#------------------------------------------------------------------------------ #$Date: 2021-11-19 01:14:06 +0200 (Fri, 19 Nov 2021) $ #$Revision: 270750 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/53/1565325.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1565325 loop_ _publ_author_name 'Xu, Bingjia' 'Song, Zicun' 'Zhang, Minmin' 'Zhang, Qingqing' 'Jiang, Long' 'Xu, Chao' 'Zhong, Lijun' 'Su, Changlin' 'Ban, Qiqi' 'Liu, Cong' 'Sun, Fengqiang' 'Zhang, Yi' 'Chi, Zhenguo' 'Zhao, Zujin' 'Shi, Guang' _publ_section_title ; Controlling the Thermally Activated Delayed Fluorescence of Axially Chiral Organic Emitters and Their Racemate for Information Encryption ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D1SC04738H _journal_year 2021 _chemical_formula_moiety 'C55 H34 N4 O2, C4 H8 O2' _chemical_formula_sum 'C59 H42 N4 O4' _chemical_formula_weight 870.96 _chemical_name_systematic (S)-CzACN-SCer _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2017-12-14 _audit_creation_method ; Olex2 1.2 (compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227) ; _audit_update_record ; 2021-06-29 deposited with the CCDC. 2021-11-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.9114(3) _cell_length_b 16.3200(5) _cell_length_c 26.1644(9) _cell_measurement_reflns_used 4535 _cell_measurement_temperature 293.3(4) _cell_measurement_theta_max 73.7650 _cell_measurement_theta_min 4.3420 _cell_volume 4659.2(2) _computing_cell_refinement 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_environment air _diffrn_ambient_temperature 293.3(4) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2913 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.966 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -110.00 -18.00 1.00 30.42 -- -38.50 -37.00 -30.00 92 2 \w 1.00 77.00 1.00 30.42 -- 43.56 -99.00-180.00 76 3 \w 43.00 123.00 1.00 47.50 -- 107.38 -45.00-150.00 80 4 \w 33.00 104.00 1.00 47.50 -- 107.38 -94.00 90.00 71 5 \w 35.00 94.00 1.00 47.50 -- 107.38 -94.00-180.00 59 6 \w 38.00 141.00 1.00 47.50 -- 107.38 -15.00 -90.00 103 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0030330000 _diffrn_orient_matrix_UB_12 -0.0665331000 _diffrn_orient_matrix_UB_13 -0.0418056000 _diffrn_orient_matrix_UB_21 0.0264077000 _diffrn_orient_matrix_UB_22 0.0661572000 _diffrn_orient_matrix_UB_23 -0.0405322000 _diffrn_orient_matrix_UB_31 0.1385834000 _diffrn_orient_matrix_UB_32 -0.0109585000 _diffrn_orient_matrix_UB_33 0.0086586000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0504 _diffrn_reflns_av_unetI/netI 0.0585 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.966 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 14493 _diffrn_reflns_point_group_measured_fraction_full 0.989 _diffrn_reflns_point_group_measured_fraction_max 0.948 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 74.794 _diffrn_reflns_theta_min 4.331 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.622 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.35021 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour red _exptl_crystal_colour_primary red _exptl_crystal_density_diffrn 1.242 _exptl_crystal_description needle _exptl_crystal_F_000 1824 _exptl_crystal_preparation Luminescent _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: dichloromethane and ethyl acetate' _exptl_crystal_size_max 0.900 _exptl_crystal_size_mid 0.040 _exptl_crystal_size_min 0.020 _refine_diff_density_max 0.260 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.041 _refine_ls_abs_structure_details ; Flack x determined using 2078 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.1(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 608 _refine_ls_number_reflns 9084 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.055 _refine_ls_R_factor_all 0.0793 _refine_ls_R_factor_gt 0.0624 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0747P)^2^+0.2411P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1539 _refine_ls_wR_factor_ref 0.1758 _reflns_Friedel_coverage 0.766 _reflns_Friedel_fraction_full 0.982 _reflns_Friedel_fraction_max 0.925 _reflns_number_gt 7002 _reflns_number_total 9084 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; 17121305.res created by SHELXL-2014/7 TITL 17121305_a.res in P2(1)2(1)2(1) REM Old TITL REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.139, Rweak 0.048, Alpha 0.002, Orientation as input REM Flack x = -0.290 ( 0.284 ) from Parsons' quotients REM Formula found by SHELXT: C57 N7 O3 CELL 1.54184 10.9114 16.32 26.1644 90 90 90 ZERR 4 0.0003 0.0005 0.0009 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N O UNIT 236 168 16 16 L.S. 10 PLAN 20 BOND $H list 4 fmap 2 MORE -1 CONF ACTA REM REM REM WGHT 0.074700 0.241100 FVAR 0.41294 O001 4 0.553000 0.586921 0.599813 11.00000 0.05836 0.04818 = 0.04695 0.00664 -0.01007 -0.00956 O002 4 0.379484 0.495618 0.660213 11.00000 0.06143 0.05056 = 0.04709 0.00492 -0.00587 -0.00901 N003 3 0.332807 0.511663 0.447919 11.00000 0.06514 0.05336 = 0.04475 -0.00359 -0.00976 0.01587 N004 3 0.164670 0.418057 0.508235 11.00000 0.05284 0.05019 = 0.06865 -0.00950 -0.01897 0.00348 O005 4 0.114093 0.759924 0.629834 11.00000 0.08351 0.09705 = 0.07356 -0.01584 0.00050 0.01815 C006 1 0.275491 0.582668 0.426784 11.00000 0.05275 0.05297 = 0.05280 0.00203 -0.00534 0.00709 C007 1 0.457785 0.543828 0.578981 11.00000 0.05175 0.03920 = 0.04636 -0.00021 -0.00719 -0.00286 C008 1 0.373878 0.500535 0.608449 11.00000 0.04834 0.04237 = 0.04723 0.00615 -0.00591 -0.00137 O009 4 0.192741 0.659685 0.582508 11.00000 0.11540 0.08485 = 0.08433 -0.02473 -0.00915 0.01129 C00A 1 0.441742 0.547494 0.526633 11.00000 0.05365 0.04733 = 0.04572 0.00406 -0.00308 0.00152 C00B 1 0.391907 0.569763 0.687674 11.00000 0.06078 0.04807 = 0.04290 0.00472 -0.00210 0.00163 C00C 1 0.632913 0.544147 0.632597 11.00000 0.04724 0.04520 = 0.05056 0.00509 -0.00746 -0.00881 C00D 1 0.613257 0.547545 0.684207 11.00000 0.04909 0.04385 = 0.05090 0.00474 -0.00544 -0.00885 C00E 1 0.524887 0.595362 0.496567 11.00000 0.06044 0.05770 = 0.04843 0.00584 -0.00253 0.00128 C00F 1 0.279394 0.457394 0.583771 11.00000 0.04967 0.04620 = 0.05459 0.00134 -0.00664 -0.00048 C00G 1 0.695718 0.504531 0.717084 11.00000 0.04818 0.05422 = 0.05724 0.00942 -0.00798 -0.00986 C00H 1 0.345066 0.506227 0.501800 11.00000 0.05455 0.04920 = 0.04952 -0.00353 -0.00891 0.00642 C00I 1 0.054453 0.456504 0.494900 11.00000 0.04758 0.05598 = 0.05809 -0.00279 -0.00701 0.00243 N00J 3 0.591553 0.634447 0.473217 11.00000 0.07925 0.08208 = 0.07288 0.01279 0.00610 -0.00699 C00K 1 0.515550 0.666192 0.733834 11.00000 0.08087 0.04705 = 0.04424 0.00302 -0.00229 -0.00832 C00L 1 0.169332 0.341829 0.484669 11.00000 0.05814 0.04826 = 0.06087 -0.00285 -0.00832 -0.00042 C00M 1 0.264607 0.460000 0.530784 11.00000 0.05097 0.04506 = 0.05567 -0.00340 -0.01123 0.00478 C00N 1 0.505484 0.593802 0.703342 11.00000 0.06225 0.04737 = 0.04091 0.00358 -0.00079 -0.00291 C00O 1 0.251542 0.584952 0.375150 11.00000 0.05934 0.05870 = 0.05536 0.00405 -0.00544 0.00005 C00P 1 0.732110 0.504387 0.610829 11.00000 0.05377 0.06645 = 0.05492 -0.00068 0.00227 -0.01144 AFIX 43 H00P 2 0.743272 0.504509 0.575590 11.00000 -1.20000 AFIX 0 C00Q 1 0.399739 0.459325 0.416239 11.00000 0.05488 0.05040 = 0.06440 -0.00711 -0.00597 0.00399 C00R 1 0.195109 0.411496 0.614668 11.00000 0.05320 0.06133 = 0.06340 0.00502 -0.00629 -0.00953 C00S 1 0.678773 0.500039 0.770488 11.00000 0.06205 0.07351 = 0.05517 0.01327 -0.00794 -0.00675 AFIX 43 H00S 2 0.612226 0.526410 0.785410 11.00000 -1.20000 AFIX 0 C00T 1 0.285050 0.613004 0.699581 11.00000 0.05925 0.07420 = 0.05405 0.00709 -0.00276 0.00540 AFIX 43 H00T 2 0.209149 0.595001 0.687946 11.00000 -1.20000 AFIX 0 C00U 1 0.204003 0.722889 0.604650 11.00000 0.08370 0.07146 = 0.05529 0.00844 -0.00148 0.01442 N00V 3 0.129664 0.375003 0.639565 11.00000 0.07855 0.09012 = 0.09771 0.01745 -0.00065 -0.02574 C00W 1 0.294447 0.682446 0.728741 11.00000 0.08029 0.07114 = 0.05582 0.00373 0.00334 0.02497 AFIX 43 H00W 2 0.223959 0.711672 0.736926 11.00000 -1.20000 AFIX 0 C00X 1 0.629873 0.696598 0.751090 11.00000 0.09085 0.06164 = 0.05550 0.00008 -0.00526 -0.02052 AFIX 43 H00X 2 0.701923 0.669086 0.742959 11.00000 -1.20000 AFIX 0 C00Y 1 0.797486 0.463230 0.694739 11.00000 0.04868 0.05909 = 0.07470 0.01122 -0.00742 -0.00991 C00Z 1 0.378586 0.461548 0.363805 11.00000 0.06720 0.07128 = 0.05719 -0.01502 -0.00160 0.00764 C010 1 0.407884 0.710171 0.746408 11.00000 0.09832 0.05327 = 0.04555 0.00313 0.00124 0.01046 C011 1 0.273467 0.511365 0.342244 11.00000 0.06521 0.07655 = 0.05795 -0.00524 -0.00219 -0.00051 C012 1 0.062641 0.328872 0.456029 11.00000 0.05890 0.05494 = 0.07182 -0.00779 -0.00664 -0.00791 C013 1 0.244136 0.648256 0.458385 11.00000 0.07677 0.05857 = 0.06956 -0.00343 0.00027 0.01495 AFIX 43 H013 2 0.261001 0.645688 0.493189 11.00000 -1.20000 AFIX 0 C014 1 0.261657 0.283007 0.487002 11.00000 0.06859 0.06450 = 0.10536 0.00406 -0.01883 0.01016 AFIX 43 H014 2 0.332636 0.291000 0.506038 11.00000 -1.20000 AFIX 0 C015 1 0.813453 0.464894 0.642130 11.00000 0.04814 0.07883 = 0.07137 0.00014 -0.00161 0.00186 AFIX 43 H015 2 0.880862 0.438614 0.627832 11.00000 -1.20000 AFIX 0 C016 1 0.010514 0.532214 0.509698 11.00000 0.06644 0.06551 = 0.07696 -0.00217 0.00157 0.00635 AFIX 43 H016 2 0.054365 0.566202 0.531596 11.00000 -1.20000 AFIX 0 C017 1 -0.011279 0.403741 0.462963 11.00000 0.05088 0.07229 = 0.06962 -0.00054 -0.00660 -0.01084 C018 1 0.415877 0.782424 0.775771 11.00000 0.14502 0.05773 = 0.06608 -0.00844 0.00130 0.01719 AFIX 43 H018 2 0.345506 0.811783 0.783945 11.00000 -1.20000 AFIX 0 C019 1 -0.167474 0.502580 0.457752 11.00000 0.05561 0.09730 = 0.08475 0.00401 -0.00723 0.01215 AFIX 43 H019 2 -0.243235 0.519247 0.445218 11.00000 -1.20000 AFIX 0 C01A 1 0.487076 0.405311 0.436519 11.00000 0.07332 0.06661 = 0.08250 -0.00088 -0.00870 0.01514 AFIX 43 H01A 2 0.501824 0.405564 0.471527 11.00000 -1.20000 AFIX 0 C01B 1 0.047019 0.257752 0.429083 11.00000 0.08878 0.07578 = 0.08768 -0.02153 -0.00708 -0.01842 AFIX 43 H01B 2 -0.023234 0.249157 0.409684 11.00000 -1.20000 AFIX 0 C01C 1 0.187946 0.717276 0.438181 11.00000 0.08878 0.07072 = 0.08788 -0.00120 0.00716 0.02299 AFIX 43 H01C 2 0.168179 0.761449 0.459068 11.00000 -1.20000 AFIX 0 C01D 1 -0.123628 0.428139 0.443928 11.00000 0.05116 0.09970 = 0.08154 -0.00080 -0.01034 -0.00698 AFIX 43 H01D 2 -0.168067 0.394284 0.422156 11.00000 -1.20000 AFIX 0 C01E 1 0.758761 0.457515 0.800468 11.00000 0.07984 0.10248 = 0.06681 0.02789 -0.01688 -0.01142 AFIX 43 H01E 2 0.746814 0.455529 0.835639 11.00000 -1.20000 AFIX 0 C01F 1 -0.103354 0.554890 0.489966 11.00000 0.07856 0.08550 = 0.08718 0.01039 0.00530 0.02319 AFIX 43 H01F 2 -0.136641 0.605545 0.498474 11.00000 -1.20000 AFIX 0 C01G 1 0.192978 0.656178 0.355985 11.00000 0.07877 0.08344 = 0.07460 0.01739 -0.01534 0.01273 AFIX 43 H01G 2 0.175248 0.659791 0.321291 11.00000 -1.20000 AFIX 0 C01H 1 0.877386 0.419472 0.727678 11.00000 0.05133 0.09135 = 0.09738 0.02326 -0.01176 0.00403 AFIX 43 H01H 2 0.944252 0.391918 0.713878 11.00000 -1.20000 AFIX 0 C01I 1 0.858349 0.417000 0.778687 11.00000 0.06923 0.11358 = 0.09178 0.03903 -0.02394 -0.00524 AFIX 43 H01I 2 0.912208 0.387988 0.799458 11.00000 -1.20000 AFIX 0 C01J 1 0.550518 0.352758 0.406384 11.00000 0.09021 0.08055 = 0.13481 -0.01715 -0.00211 0.03592 AFIX 43 H01J 2 0.606530 0.316158 0.420406 11.00000 -1.20000 AFIX 0 C01K 1 0.633791 0.766687 0.779796 11.00000 0.13544 0.06475 = 0.06442 -0.00891 -0.00248 -0.02753 AFIX 43 H01K 2 0.709125 0.786123 0.791173 11.00000 -1.20000 AFIX 0 C01L 1 0.528887 0.809063 0.792216 11.00000 0.17908 0.05591 = 0.06443 -0.01001 -0.00326 -0.00518 AFIX 43 H01L 2 0.534423 0.856294 0.811968 11.00000 -1.20000 AFIX 0 C01M 1 0.241411 0.211253 0.459063 11.00000 0.09812 0.05910 = 0.13304 -0.00836 -0.01579 0.02038 AFIX 43 H01M 2 0.300646 0.170283 0.459362 11.00000 -1.20000 AFIX 0 C01N 1 0.446274 0.407602 0.333414 11.00000 0.11537 0.11031 = 0.08449 -0.03205 0.00370 0.02930 AFIX 43 H01N 2 0.434100 0.407592 0.298234 11.00000 -1.20000 AFIX 0 C01O 1 0.162264 0.719309 0.387415 11.00000 0.08894 0.08994 = 0.08952 0.01330 -0.00572 0.03206 AFIX 43 H01O 2 0.122796 0.764882 0.373834 11.00000 -1.20000 AFIX 0 C01P 1 0.136733 0.199880 0.431342 11.00000 0.10002 0.06882 = 0.13875 -0.03008 -0.00741 0.00452 AFIX 43 H01P 2 0.126414 0.151116 0.413461 11.00000 -1.20000 AFIX 0 C01Q 1 0.156269 0.458246 0.342830 11.00000 0.08314 0.09454 = 0.10331 -0.01441 -0.00849 -0.02638 AFIX 137 H01Q 2 0.138640 0.441664 0.377257 11.00000 -1.50000 H01R 2 0.168574 0.410572 0.321958 11.00000 -1.50000 H01S 2 0.088773 0.489495 0.329640 11.00000 -1.50000 AFIX 0 C01R 1 0.318617 0.770001 0.607024 11.00000 0.09900 0.08468 = 0.10136 0.02183 0.01523 -0.00050 AFIX 137 H01X 2 0.321707 0.807753 0.578916 11.00000 -1.50000 H01Y 2 0.387124 0.733224 0.605081 11.00000 -1.50000 H 2 0.321902 0.799807 0.638627 11.00000 -1.50000 AFIX 0 C01S 1 0.299711 0.538044 0.287271 11.00000 0.10486 0.10720 = 0.05947 -0.00378 -0.00280 -0.00705 AFIX 137 H01T 2 0.229532 0.566111 0.273735 11.00000 -1.50000 H01U 2 0.316854 0.490660 0.266739 11.00000 -1.50000 H01V 2 0.369214 0.574104 0.286842 11.00000 -1.50000 AFIX 0 C01T 1 0.529800 0.354936 0.354099 11.00000 0.11991 0.11600 = 0.12967 -0.04277 0.00901 0.04515 AFIX 43 H01W 2 0.573544 0.319936 0.332791 11.00000 -1.20000 AFIX 0 C01U 1 -0.008065 0.726522 0.625886 11.00000 0.06978 0.19639 = 0.12843 -0.02778 -0.00767 0.01357 AFIX 23 H01Z 2 -0.064856 0.770440 0.617943 11.00000 -1.20000 HA 2 -0.010433 0.687553 0.597911 11.00000 -1.20000 AFIX 0 C01V 1 -0.046796 0.686914 0.671349 11.00000 0.09618 0.18668 = 0.22912 0.08907 -0.01157 -0.02453 AFIX 137 H01 2 -0.134546 0.682659 0.671487 11.00000 -1.50000 HB 2 -0.020522 0.718194 0.700427 11.00000 -1.50000 HC 2 -0.011537 0.633079 0.672907 11.00000 -1.50000 AFIX 0 HKLF 4 REM 17121305_a.res in P2(1)2(1)2(1) REM R1 = 0.0624 for 7002 Fo > 4sig(Fo) and 0.0793 for all 9084 data REM 608 parameters refined using 0 restraints END WGHT 0.0747 0.2359 REM Highest difference peak 0.260, deepest hole -0.190, 1-sigma level 0.041 Q1 1 0.0002 0.3832 0.4195 11.00000 0.05 0.26 Q2 1 0.0474 0.4130 0.3772 11.00000 0.05 0.23 Q3 1 0.3237 0.5561 0.3684 11.00000 0.05 0.22 Q4 1 -0.1231 0.3276 0.4045 11.00000 0.05 0.19 Q5 1 0.3519 0.4547 0.5875 11.00000 0.05 0.17 Q6 1 0.7558 0.5018 0.7143 11.00000 0.05 0.16 Q7 1 0.4732 0.4633 0.6361 11.00000 0.05 0.15 Q8 1 -0.0655 0.6149 0.5107 11.00000 0.05 0.14 Q9 1 0.6732 0.4581 0.8643 11.00000 0.05 0.13 Q10 1 0.4129 0.5030 0.5042 11.00000 0.05 0.13 Q11 1 0.1192 0.4054 0.6121 11.00000 0.05 0.13 Q12 1 0.0299 0.6682 0.6302 11.00000 0.05 0.13 Q13 1 0.4867 0.6018 0.6595 11.00000 0.05 0.13 Q14 1 -0.0780 0.2647 0.3705 11.00000 0.05 0.13 Q15 1 0.2166 0.6240 0.4232 11.00000 0.05 0.13 Q16 1 0.4787 0.5965 0.6123 11.00000 0.05 0.13 Q17 1 0.5138 0.6536 0.6411 11.00000 0.05 0.13 Q18 1 0.5532 0.6419 0.6258 11.00000 0.05 0.13 Q19 1 0.4702 0.4515 0.4140 11.00000 0.05 0.12 Q20 1 0.9704 0.3599 0.6946 11.00000 0.05 0.12 REM The information below was added by Olex2. REM REM R1 = 0.0624 for 7002 Fo > 4sig(Fo) and 0.0793 for all 14523 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.26, deepest hole -0.19 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0793 REM R1_gt = 0.0624 REM wR_ref = 0.1758 REM GOOF = 1.055 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 14523 REM Reflections_gt = 7002 REM Parameters = n/a REM Hole = -0.19 REM Peak = 0.26 REM Flack = -0.1(3) ; _cod_data_source_file d1sc04738h2.cif _cod_data_source_block (S)-CzACN-SCer _cod_database_code 1565325 _chemical_oxdiff_formula 'C H O N' _chemical_oxdiff_usercomment R-CzACN _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _reflns_odcompleteness_completeness 99.40 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C01U(H01Z,HA) 2.b Aromatic/amide H refined with riding coordinates: C00P(H00P), C00S(H00S), C00T(H00T), C00W(H00W), C00X(H00X), C013(H013), C014(H014), C015(H015), C016(H016), C018(H018), C019(H019), C01A(H01A), C01B(H01B), C01C(H01C), C01D(H01D), C01E(H01E), C01F(H01F), C01G(H01G), C01H(H01H), C01I(H01I), C01J(H01J), C01K(H01K), C01L(H01L), C01M(H01M), C01N(H01N), C01O(H01O), C01P(H01P), C01T(H01W) 2.c Idealised Me refined as rotating group: C01Q(H01Q,H01R,H01S), C01R(H01X,H01Y,H), C01S(H01T,H01U,H01V), C01V(H01,HB,HC) ; _shelx_shelxl_version_number 2014/7 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.925 _oxdiff_exptl_absorpt_empirical_full_min 0.540 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O001 O 0.5530(3) 0.58692(17) 0.59981(10) 0.0512(7) Uani 1 1 d . . . . . O002 O 0.3795(3) 0.49562(18) 0.66021(10) 0.0530(7) Uani 1 1 d . . . . . N003 N 0.3328(3) 0.5117(2) 0.44792(13) 0.0544(8) Uani 1 1 d . . . . . N004 N 0.1647(3) 0.4181(2) 0.50824(15) 0.0572(9) Uani 1 1 d . . . . . O005 O 0.1141(4) 0.7599(3) 0.62983(15) 0.0847(11) Uani 1 1 d . . . . . C006 C 0.2755(4) 0.5827(3) 0.42678(16) 0.0528(10) Uani 1 1 d . . . . . C007 C 0.4578(4) 0.5438(2) 0.57898(15) 0.0458(8) Uani 1 1 d . . . . . C008 C 0.3739(4) 0.5005(2) 0.60845(15) 0.0460(8) Uani 1 1 d . . . . . O009 O 0.1927(5) 0.6597(3) 0.58251(16) 0.0949(13) Uani 1 1 d . . . . . C00A C 0.4417(4) 0.5475(3) 0.52663(15) 0.0489(9) Uani 1 1 d . . . . . C00B C 0.3919(4) 0.5698(3) 0.68767(15) 0.0506(9) Uani 1 1 d . . . . . C00C C 0.6329(3) 0.5441(2) 0.63260(15) 0.0477(9) Uani 1 1 d . . . . . C00D C 0.6133(4) 0.5475(2) 0.68421(16) 0.0479(9) Uani 1 1 d . . . . . C00E C 0.5249(4) 0.5954(3) 0.49657(16) 0.0555(10) Uani 1 1 d . . . . . C00F C 0.2794(4) 0.4574(3) 0.58377(16) 0.0502(9) Uani 1 1 d . . . . . C00G C 0.6957(4) 0.5045(3) 0.71708(17) 0.0532(10) Uani 1 1 d . . . . . C00H C 0.3451(4) 0.5062(3) 0.50180(16) 0.0511(9) Uani 1 1 d . . . . . C00I C 0.0545(4) 0.4565(3) 0.49490(17) 0.0539(10) Uani 1 1 d . . . . . N00J N 0.5916(5) 0.6344(3) 0.47322(17) 0.0781(12) Uani 1 1 d . . . . . C00K C 0.5155(5) 0.6662(3) 0.73383(15) 0.0574(11) Uani 1 1 d . . . . . C00L C 0.1693(4) 0.3418(3) 0.48467(17) 0.0558(10) Uani 1 1 d . . . . . C00M C 0.2646(4) 0.4600(3) 0.53078(16) 0.0506(9) Uani 1 1 d . . . . . C00N C 0.5055(4) 0.5938(3) 0.70334(15) 0.0502(9) Uani 1 1 d . . . . . C00O C 0.2515(4) 0.5850(3) 0.37515(17) 0.0578(10) Uani 1 1 d . . . . . C00P C 0.7321(4) 0.5044(3) 0.61083(18) 0.0584(11) Uani 1 1 d . . . . . H00P H 0.7433 0.5045 0.5756 0.070 Uiso 1 1 calc R . . . . C00Q C 0.3997(4) 0.4593(3) 0.41624(18) 0.0566(10) Uani 1 1 d . . . . . C00R C 0.1951(4) 0.4115(3) 0.61467(18) 0.0593(11) Uani 1 1 d . . . . . C00S C 0.6788(4) 0.5000(3) 0.77049(18) 0.0636(12) Uani 1 1 d . . . . . H00S H 0.6122 0.5264 0.7854 0.076 Uiso 1 1 calc R . . . . C00T C 0.2851(4) 0.6130(3) 0.69958(18) 0.0625(12) Uani 1 1 d . . . . . H00T H 0.2091 0.5950 0.6879 0.075 Uiso 1 1 calc R . . . . C00U C 0.2040(5) 0.7229(4) 0.60465(19) 0.0702(13) Uani 1 1 d . . . . . N00V N 0.1297(5) 0.3750(3) 0.6396(2) 0.0888(15) Uani 1 1 d . . . . . C00W C 0.2944(5) 0.6824(3) 0.72874(18) 0.0691(14) Uani 1 1 d . . . . . H00W H 0.2240 0.7117 0.7369 0.083 Uiso 1 1 calc R . . . . C00X C 0.6299(6) 0.6966(3) 0.75109(18) 0.0693(13) Uani 1 1 d . . . . . H00X H 0.7019 0.6691 0.7430 0.083 Uiso 1 1 calc R . . . . C00Y C 0.7975(4) 0.4632(3) 0.69474(19) 0.0608(11) Uani 1 1 d . . . . . C00Z C 0.3786(5) 0.4615(3) 0.36380(18) 0.0652(12) Uani 1 1 d . . . . . C010 C 0.4079(5) 0.7102(3) 0.74641(17) 0.0657(12) Uani 1 1 d . . . . . C011 C 0.2735(5) 0.5114(4) 0.34224(19) 0.0666(12) Uani 1 1 d . . . . . C012 C 0.0626(4) 0.3289(3) 0.45603(19) 0.0619(11) Uani 1 1 d . . . . . C013 C 0.2441(5) 0.6483(3) 0.4584(2) 0.0683(13) Uani 1 1 d . . . . . H013 H 0.2610 0.6457 0.4932 0.082 Uiso 1 1 calc R . . . . C014 C 0.2617(5) 0.2830(3) 0.4870(2) 0.0795(15) Uani 1 1 d . . . . . H014 H 0.3326 0.2910 0.5060 0.095 Uiso 1 1 calc R . . . . C015 C 0.8135(4) 0.4649(3) 0.6421(2) 0.0661(12) Uani 1 1 d . . . . . H015 H 0.8809 0.4386 0.6278 0.079 Uiso 1 1 calc R . . . . C016 C 0.0105(5) 0.5322(3) 0.5097(2) 0.0696(13) Uani 1 1 d . . . . . H016 H 0.0544 0.5662 0.5316 0.084 Uiso 1 1 calc R . . . . C017 C -0.0113(4) 0.4037(3) 0.46296(19) 0.0643(12) Uani 1 1 d . . . . . C018 C 0.4159(8) 0.7824(4) 0.7758(2) 0.0896(19) Uani 1 1 d . . . . . H018 H 0.3455 0.8118 0.7839 0.108 Uiso 1 1 calc R . . . . C019 C -0.1675(5) 0.5026(4) 0.4578(2) 0.0792(15) Uani 1 1 d . . . . . H019 H -0.2432 0.5192 0.4452 0.095 Uiso 1 1 calc R . . . . C01A C 0.4871(5) 0.4053(3) 0.4365(2) 0.0741(14) Uani 1 1 d . . . . . H01A H 0.5018 0.4056 0.4715 0.089 Uiso 1 1 calc R . . . . C01B C 0.0470(6) 0.2578(4) 0.4291(2) 0.0841(16) Uani 1 1 d . . . . . H01B H -0.0232 0.2492 0.4097 0.101 Uiso 1 1 calc R . . . . C01C C 0.1879(6) 0.7173(4) 0.4382(2) 0.0825(16) Uani 1 1 d . . . . . H01C H 0.1682 0.7614 0.4591 0.099 Uiso 1 1 calc R . . . . C01D C -0.1236(5) 0.4281(4) 0.4439(2) 0.0775(15) Uani 1 1 d . . . . . H01D H -0.1681 0.3943 0.4222 0.093 Uiso 1 1 calc R . . . . C01E C 0.7588(5) 0.4575(4) 0.8005(2) 0.0830(17) Uani 1 1 d . . . . . H01E H 0.7468 0.4555 0.8356 0.100 Uiso 1 1 calc R . . . . C01F C -0.1034(6) 0.5549(4) 0.4900(2) 0.0837(16) Uani 1 1 d . . . . . H01F H -0.1366 0.6055 0.4985 0.100 Uiso 1 1 calc R . . . . C01G C 0.1930(5) 0.6562(4) 0.3560(2) 0.0789(15) Uani 1 1 d . . . . . H01G H 0.1752 0.6598 0.3213 0.095 Uiso 1 1 calc R . . . . C01H C 0.8774(5) 0.4195(4) 0.7277(2) 0.0800(16) Uani 1 1 d . . . . . H01H H 0.9443 0.3919 0.7139 0.096 Uiso 1 1 calc R . . . . C01I C 0.8583(5) 0.4170(5) 0.7787(3) 0.092(2) Uani 1 1 d . . . . . H01I H 0.9122 0.3880 0.7995 0.110 Uiso 1 1 calc R . . . . C01J C 0.5505(6) 0.3528(4) 0.4064(3) 0.102(2) Uani 1 1 d . . . . . H01J H 0.6065 0.3162 0.4204 0.122 Uiso 1 1 calc R . . . . C01K C 0.6338(8) 0.7667(4) 0.7798(2) 0.0882(19) Uani 1 1 d . . . . . H01K H 0.7091 0.7861 0.7912 0.106 Uiso 1 1 calc R . . . . C01L C 0.5289(9) 0.8091(4) 0.7922(2) 0.100(2) Uani 1 1 d . . . . . H01L H 0.5344 0.8563 0.8120 0.120 Uiso 1 1 calc R . . . . C01M C 0.2414(6) 0.2113(4) 0.4591(3) 0.097(2) Uani 1 1 d . . . . . H01M H 0.3006 0.1703 0.4594 0.116 Uiso 1 1 calc R . . . . C01N C 0.4463(7) 0.4076(5) 0.3334(3) 0.103(2) Uani 1 1 d . . . . . H01N H 0.4341 0.4076 0.2982 0.124 Uiso 1 1 calc R . . . . C01O C 0.1623(6) 0.7193(4) 0.3874(2) 0.0895(18) Uani 1 1 d . . . . . H01O H 0.1228 0.7649 0.3738 0.107 Uiso 1 1 calc R . . . . C01P C 0.1367(7) 0.1999(4) 0.4313(3) 0.103(2) Uani 1 1 d . . . . . H01P H 0.1264 0.1511 0.4135 0.123 Uiso 1 1 calc R . . . . C01Q C 0.1563(6) 0.4582(4) 0.3428(3) 0.0937(19) Uani 1 1 d . . . . . H01Q H 0.1386 0.4417 0.3773 0.140 Uiso 1 1 calc GR . . . . H01R H 0.1686 0.4106 0.3220 0.140 Uiso 1 1 calc GR . . . . H01S H 0.0888 0.4895 0.3296 0.140 Uiso 1 1 calc GR . . . . C01R C 0.3186(6) 0.7700(4) 0.6070(3) 0.0950(19) Uani 1 1 d . . . . . H01X H 0.3217 0.8078 0.5789 0.143 Uiso 1 1 calc GR . . . . H01Y H 0.3871 0.7332 0.6051 0.143 Uiso 1 1 calc GR . . . . H H 0.3219 0.7998 0.6386 0.143 Uiso 1 1 calc GR . . . . C01S C 0.2997(7) 0.5380(4) 0.2873(2) 0.0905(18) Uani 1 1 d . . . . . H01T H 0.2295 0.5661 0.2737 0.136 Uiso 1 1 calc GR . . . . H01U H 0.3169 0.4907 0.2667 0.136 Uiso 1 1 calc GR . . . . H01V H 0.3692 0.5741 0.2868 0.136 Uiso 1 1 calc GR . . . . C01T C 0.5298(8) 0.3549(5) 0.3541(3) 0.122(3) Uani 1 1 d . . . . . H01W H 0.5735 0.3199 0.3328 0.146 Uiso 1 1 calc R . . . . C01U C -0.0081(7) 0.7265(7) 0.6259(4) 0.132(3) Uani 1 1 d . . . . . H01Z H -0.0649 0.7704 0.6179 0.158 Uiso 1 1 calc R . . . . HA H -0.0104 0.6876 0.5979 0.158 Uiso 1 1 calc R . . . . C01V C -0.0468(8) 0.6869(7) 0.6713(5) 0.171(5) Uani 1 1 d . . . . . H01 H -0.1345 0.6827 0.6715 0.256 Uiso 1 1 calc GR . . . . HB H -0.0205 0.7182 0.7004 0.256 Uiso 1 1 calc GR . . . . HC H -0.0115 0.6331 0.6729 0.256 Uiso 1 1 calc GR . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O001 0.0584(15) 0.0482(15) 0.0470(14) 0.0066(12) -0.0101(12) -0.0096(13) O002 0.0614(16) 0.0506(15) 0.0471(15) 0.0049(13) -0.0059(13) -0.0090(14) N003 0.065(2) 0.053(2) 0.0448(17) -0.0036(15) -0.0098(16) 0.0159(17) N004 0.0528(18) 0.0502(19) 0.069(2) -0.0095(17) -0.0190(17) 0.0035(16) O005 0.084(2) 0.097(3) 0.074(2) -0.016(2) 0.001(2) 0.018(2) C006 0.053(2) 0.053(2) 0.053(2) 0.0020(19) -0.0053(18) 0.0071(19) C007 0.052(2) 0.0392(18) 0.0464(19) -0.0002(16) -0.0072(17) -0.0029(17) C008 0.0483(19) 0.0424(19) 0.047(2) 0.0061(17) -0.0059(16) -0.0014(17) O009 0.115(3) 0.085(3) 0.084(3) -0.025(2) -0.009(2) 0.011(3) C00A 0.054(2) 0.047(2) 0.046(2) 0.0041(17) -0.0031(17) 0.0015(18) C00B 0.061(2) 0.048(2) 0.043(2) 0.0047(17) -0.0021(18) 0.002(2) C00C 0.047(2) 0.045(2) 0.051(2) 0.0051(17) -0.0075(17) -0.0088(17) C00D 0.0491(19) 0.044(2) 0.051(2) 0.0047(17) -0.0054(17) -0.0089(18) C00E 0.060(2) 0.058(2) 0.048(2) 0.006(2) -0.0025(19) 0.001(2) C00F 0.050(2) 0.046(2) 0.055(2) 0.0013(18) -0.0066(17) -0.0005(18) C00G 0.048(2) 0.054(2) 0.057(2) 0.009(2) -0.0080(18) -0.010(2) C00H 0.055(2) 0.049(2) 0.050(2) -0.0035(18) -0.0089(17) 0.0064(19) C00I 0.048(2) 0.056(2) 0.058(2) -0.003(2) -0.0070(18) 0.0024(19) N00J 0.079(3) 0.082(3) 0.073(3) 0.013(2) 0.006(2) -0.007(3) C00K 0.081(3) 0.047(2) 0.044(2) 0.0030(18) -0.002(2) -0.008(2) C00L 0.058(2) 0.048(2) 0.061(3) -0.003(2) -0.008(2) -0.0004(19) C00M 0.051(2) 0.045(2) 0.056(2) -0.0034(18) -0.0112(18) 0.0048(18) C00N 0.062(2) 0.047(2) 0.0409(19) 0.0036(16) -0.0008(17) -0.0029(19) C00O 0.059(2) 0.059(3) 0.055(2) 0.004(2) -0.005(2) 0.000(2) C00P 0.054(2) 0.066(3) 0.055(2) -0.001(2) 0.0023(19) -0.011(2) C00Q 0.055(2) 0.050(2) 0.064(3) -0.007(2) -0.006(2) 0.004(2) C00R 0.053(2) 0.061(3) 0.063(3) 0.005(2) -0.006(2) -0.010(2) C00S 0.062(2) 0.074(3) 0.055(2) 0.013(2) -0.008(2) -0.007(3) C00T 0.059(2) 0.074(3) 0.054(2) 0.007(2) -0.003(2) 0.005(2) C00U 0.084(3) 0.071(3) 0.055(3) 0.008(2) -0.001(2) 0.014(3) N00V 0.079(3) 0.090(3) 0.098(3) 0.017(3) -0.001(3) -0.026(3) C00W 0.080(3) 0.071(3) 0.056(3) 0.004(2) 0.003(2) 0.025(3) C00X 0.091(3) 0.062(3) 0.056(3) 0.000(2) -0.005(3) -0.021(3) C00Y 0.049(2) 0.059(3) 0.075(3) 0.011(2) -0.007(2) -0.010(2) C00Z 0.067(3) 0.071(3) 0.057(2) -0.015(2) -0.002(2) 0.008(3) C010 0.098(4) 0.053(2) 0.046(2) 0.003(2) 0.001(2) 0.010(3) C011 0.065(3) 0.077(3) 0.058(3) -0.005(2) -0.002(2) -0.001(3) C012 0.059(2) 0.055(3) 0.072(3) -0.008(2) -0.007(2) -0.008(2) C013 0.077(3) 0.059(3) 0.070(3) -0.003(2) 0.000(3) 0.015(2) C014 0.069(3) 0.065(3) 0.105(4) 0.004(3) -0.019(3) 0.010(3) C015 0.048(2) 0.079(3) 0.071(3) 0.000(3) -0.002(2) 0.002(2) C016 0.066(3) 0.066(3) 0.077(3) -0.002(3) 0.002(2) 0.006(2) C017 0.051(2) 0.072(3) 0.070(3) -0.001(2) -0.007(2) -0.011(2) C018 0.145(6) 0.058(3) 0.066(3) -0.008(3) 0.001(4) 0.017(4) C019 0.056(3) 0.097(4) 0.085(4) 0.004(3) -0.007(3) 0.012(3) C01A 0.073(3) 0.067(3) 0.082(3) -0.001(3) -0.009(3) 0.015(3) C01B 0.089(4) 0.076(3) 0.088(4) -0.022(3) -0.007(3) -0.018(3) C01C 0.089(4) 0.071(3) 0.088(4) -0.001(3) 0.007(3) 0.023(3) C01D 0.051(2) 0.100(4) 0.082(3) -0.001(3) -0.010(2) -0.007(3) C01E 0.080(3) 0.102(4) 0.067(3) 0.028(3) -0.017(3) -0.011(3) C01F 0.079(3) 0.085(4) 0.087(4) 0.010(3) 0.005(3) 0.023(3) C01G 0.079(3) 0.083(4) 0.075(3) 0.017(3) -0.015(3) 0.013(3) C01H 0.051(2) 0.091(4) 0.097(4) 0.023(3) -0.012(3) 0.004(3) C01I 0.069(3) 0.114(5) 0.092(4) 0.039(4) -0.024(3) -0.005(4) C01J 0.090(4) 0.081(4) 0.135(6) -0.017(4) -0.002(4) 0.036(4) C01K 0.135(6) 0.065(3) 0.064(3) -0.009(3) -0.002(3) -0.028(4) C01L 0.179(8) 0.056(3) 0.064(3) -0.010(3) -0.003(4) -0.005(4) C01M 0.098(4) 0.059(3) 0.133(6) -0.008(4) -0.016(4) 0.020(3) C01N 0.115(5) 0.110(5) 0.084(4) -0.032(4) 0.004(4) 0.029(5) C01O 0.089(4) 0.090(4) 0.090(4) 0.013(4) -0.006(3) 0.032(3) C01P 0.100(5) 0.069(4) 0.139(6) -0.030(4) -0.007(4) 0.005(4) C01Q 0.083(4) 0.095(4) 0.103(5) -0.014(4) -0.008(3) -0.026(3) C01R 0.099(4) 0.085(4) 0.101(5) 0.022(4) 0.015(4) -0.001(4) C01S 0.105(4) 0.107(5) 0.059(3) -0.004(3) -0.003(3) -0.007(4) C01T 0.120(6) 0.116(6) 0.130(7) -0.043(5) 0.009(5) 0.045(5) C01U 0.070(4) 0.196(10) 0.128(7) -0.028(7) -0.008(4) 0.014(6) C01V 0.096(6) 0.187(11) 0.229(12) 0.089(10) -0.012(7) -0.025(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C007 O001 C00C 117.3(3) . . ? C008 O002 C00B 117.4(3) . . ? C00H N003 C006 118.5(3) . . ? C00Q N003 C006 119.7(4) . . ? C00Q N003 C00H 120.1(3) . . ? C00I N004 C00M 123.3(3) . . ? C00L N004 C00I 108.8(3) . . ? C00L N004 C00M 126.1(4) . . ? C00U O005 C01U 118.4(5) . . ? C00O C006 N003 119.0(4) . . ? C00O C006 C013 121.0(4) . . ? C013 C006 N003 120.0(4) . . ? O001 C007 C008 122.7(3) . . ? O001 C007 C00A 118.0(4) . . ? C00A C007 C008 119.2(4) . . ? O002 C008 C007 123.6(3) . . ? O002 C008 C00F 117.5(3) . . ? C007 C008 C00F 118.9(4) . . ? C007 C00A C00E 119.2(4) . . ? C007 C00A C00H 122.1(4) . . ? C00H C00A C00E 118.8(4) . . ? C00N C00B O002 119.1(4) . . ? C00N C00B C00T 123.1(4) . . ? C00T C00B O002 117.7(4) . . ? C00D C00C O001 118.9(4) . . ? C00D C00C C00P 123.2(4) . . ? C00P C00C O001 117.8(4) . . ? C00C C00D C00G 118.4(4) . . ? C00C C00D C00N 118.5(4) . . ? C00G C00D C00N 123.1(4) . . ? N00J C00E C00A 178.9(5) . . ? C008 C00F C00R 118.2(4) . . ? C00M C00F C008 121.7(4) . . ? C00M C00F C00R 120.1(4) . . ? C00S C00G C00D 122.6(4) . . ? C00S C00G C00Y 118.9(4) . . ? C00Y C00G C00D 118.4(4) . . ? C00A C00H N003 119.9(4) . . ? C00M C00H N003 121.2(4) . . ? C00M C00H C00A 118.8(4) . . ? C016 C00I N004 129.0(4) . . ? C016 C00I C017 122.7(4) . . ? C017 C00I N004 108.3(4) . . ? C00X C00K C00N 122.3(5) . . ? C010 C00K C00N 119.0(4) . . ? C010 C00K C00X 118.6(4) . . ? N004 C00L C012 110.0(4) . . ? N004 C00L C014 128.6(4) . . ? C014 C00L C012 121.4(4) . . ? C00F C00M N004 119.2(4) . . ? C00H C00M N004 121.6(4) . . ? C00H C00M C00F 119.2(4) . . ? C00B C00N C00D 118.2(4) . . ? C00B C00N C00K 118.4(4) . . ? C00K C00N C00D 123.2(4) . . ? C006 C00O C011 120.8(4) . . ? C006 C00O C01G 117.1(5) . . ? C01G C00O C011 121.8(4) . . ? C00C C00P H00P 120.6 . . ? C015 C00P C00C 118.8(4) . . ? C015 C00P H00P 120.6 . . ? N003 C00Q C01A 121.0(4) . . ? C00Z C00Q N003 118.8(4) . . ? C00Z C00Q C01A 120.1(5) . . ? N00V C00R C00F 179.1(5) . . ? C00G C00S H00S 119.6 . . ? C01E C00S C00G 120.8(5) . . ? C01E C00S H00S 119.6 . . ? C00B C00T H00T 120.7 . . ? C00W C00T C00B 118.6(5) . . ? C00W C00T H00T 120.7 . . ? O005 C00U C01R 111.7(5) . . ? O009 C00U O005 124.1(6) . . ? O009 C00U C01R 124.2(6) . . ? C00T C00W H00W 119.4 . . ? C00T C00W C010 121.2(5) . . ? C010 C00W H00W 119.4 . . ? C00K C00X H00X 120.2 . . ? C01K C00X C00K 119.7(6) . . ? C01K C00X H00X 120.2 . . ? C015 C00Y C00G 119.7(4) . . ? C015 C00Y C01H 122.4(5) . . ? C01H C00Y C00G 117.9(5) . . ? C00Q C00Z C011 120.4(4) . . ? C00Q C00Z C01N 117.2(5) . . ? C01N C00Z C011 121.8(5) . . ? C00W C010 C00K 119.6(4) . . ? C00W C010 C018 120.4(6) . . ? C018 C010 C00K 120.0(6) . . ? C00O C011 C00Z 109.7(4) . . ? C00O C011 C01Q 108.2(4) . . ? C00O C011 C01S 110.0(5) . . ? C00Z C011 C01Q 108.8(5) . . ? C00Z C011 C01S 111.2(5) . . ? C01S C011 C01Q 108.9(5) . . ? C00L C012 C017 105.3(4) . . ? C01B C012 C00L 120.5(5) . . ? C01B C012 C017 134.2(5) . . ? C006 C013 H013 119.8 . . ? C01C C013 C006 120.4(5) . . ? C01C C013 H013 119.8 . . ? C00L C014 H014 121.9 . . ? C00L C014 C01M 116.1(5) . . ? C01M C014 H014 121.9 . . ? C00P C015 C00Y 121.4(5) . . ? C00P C015 H015 119.3 . . ? C00Y C015 H015 119.3 . . ? C00I C016 H016 121.9 . . ? C00I C016 C01F 116.3(5) . . ? C01F C016 H016 121.9 . . ? C00I C017 C012 107.6(4) . . ? C01D C017 C00I 119.5(5) . . ? C01D C017 C012 132.8(5) . . ? C010 C018 H018 120.3 . . ? C01L C018 C010 119.3(7) . . ? C01L C018 H018 120.3 . . ? C01D C019 H019 118.8 . . ? C01D C019 C01F 122.4(5) . . ? C01F C019 H019 118.8 . . ? C00Q C01A H01A 119.2 . . ? C01J C01A C00Q 121.7(6) . . ? C01J C01A H01A 119.2 . . ? C012 C01B H01B 120.8 . . ? C01P C01B C012 118.4(6) . . ? C01P C01B H01B 120.8 . . ? C013 C01C H01C 120.5 . . ? C01O C01C C013 118.9(6) . . ? C01O C01C H01C 120.5 . . ? C017 C01D H01D 120.8 . . ? C019 C01D C017 118.4(5) . . ? C019 C01D H01D 120.8 . . ? C00S C01E H01E 119.8 . . ? C00S C01E C01I 120.4(5) . . ? C01I C01E H01E 119.8 . . ? C016 C01F H01F 119.7 . . ? C019 C01F C016 120.7(6) . . ? C019 C01F H01F 119.7 . . ? C00O C01G H01G 119.4 . . ? C01O C01G C00O 121.2(5) . . ? C01O C01G H01G 119.4 . . ? C00Y C01H H01H 119.3 . . ? C01I C01H C00Y 121.4(6) . . ? C01I C01H H01H 119.3 . . ? C01E C01I H01I 119.7 . . ? C01H C01I C01E 120.6(5) . . ? C01H C01I H01I 119.7 . . ? C01A C01J H01J 120.8 . . ? C01A C01J C01T 118.3(6) . . ? C01T C01J H01J 120.8 . . ? C00X C01K H01K 119.2 . . ? C00X C01K C01L 121.6(7) . . ? C01L C01K H01K 119.2 . . ? C018 C01L H01L 119.6 . . ? C01K C01L C018 120.8(5) . . ? C01K C01L H01L 119.6 . . ? C014 C01M H01M 119.2 . . ? C01P C01M C014 121.6(6) . . ? C01P C01M H01M 119.2 . . ? C00Z C01N H01N 119.2 . . ? C01T C01N C00Z 121.6(6) . . ? C01T C01N H01N 119.2 . . ? C01C C01O C01G 121.5(6) . . ? C01C C01O H01O 119.3 . . ? C01G C01O H01O 119.3 . . ? C01B C01P C01M 122.0(6) . . ? C01B C01P H01P 119.0 . . ? C01M C01P H01P 119.0 . . ? C011 C01Q H01Q 109.5 . . ? C011 C01Q H01R 109.5 . . ? C011 C01Q H01S 109.5 . . ? H01Q C01Q H01R 109.5 . . ? H01Q C01Q H01S 109.5 . . ? H01R C01Q H01S 109.5 . . ? C00U C01R H01X 109.5 . . ? C00U C01R H01Y 109.5 . . ? C00U C01R H 109.5 . . ? H01X C01R H01Y 109.5 . . ? H01X C01R H 109.5 . . ? H01Y C01R H 109.5 . . ? C011 C01S H01T 109.5 . . ? C011 C01S H01U 109.5 . . ? C011 C01S H01V 109.5 . . ? H01T C01S H01U 109.5 . . ? H01T C01S H01V 109.5 . . ? H01U C01S H01V 109.5 . . ? C01J C01T H01W 119.5 . . ? C01N C01T C01J 121.1(6) . . ? C01N C01T H01W 119.5 . . ? O005 C01U H01Z 109.0 . . ? O005 C01U HA 109.0 . . ? H01Z C01U HA 107.8 . . ? C01V C01U O005 112.8(7) . . ? C01V C01U H01Z 109.0 . . ? C01V C01U HA 109.0 . . ? C01U C01V H01 109.5 . . ? C01U C01V HB 109.5 . . ? C01U C01V HC 109.5 . . ? H01 C01V HB 109.5 . . ? H01 C01V HC 109.5 . . ? HB C01V HC 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O001 C007 1.368(5) . ? O001 C00C 1.408(5) . ? O002 C008 1.358(5) . ? O002 C00B 1.414(5) . ? N003 C006 1.428(5) . ? N003 C00H 1.419(5) . ? N003 C00Q 1.396(6) . ? N004 C00I 1.401(5) . ? N004 C00L 1.389(6) . ? N004 C00M 1.416(5) . ? O005 C00U 1.327(7) . ? O005 C01U 1.444(9) . ? C006 C00O 1.377(6) . ? C006 C013 1.395(7) . ? C007 C008 1.390(6) . ? C007 C00A 1.382(5) . ? C008 C00F 1.406(6) . ? O009 C00U 1.189(7) . ? C00A C00E 1.433(6) . ? C00A C00H 1.410(6) . ? C00B C00N 1.363(6) . ? C00B C00T 1.398(6) . ? C00C C00D 1.368(6) . ? C00C C00P 1.385(6) . ? C00D C00G 1.429(6) . ? C00D C00N 1.484(6) . ? C00E N00J 1.144(6) . ? C00F C00M 1.396(6) . ? C00F C00R 1.435(6) . ? C00G C00S 1.411(6) . ? C00G C00Y 1.425(7) . ? C00H C00M 1.384(6) . ? C00I C016 1.381(7) . ? C00I C017 1.398(6) . ? C00K C00N 1.430(6) . ? C00K C00X 1.416(7) . ? C00K C010 1.415(7) . ? C00L C012 1.401(6) . ? C00L C014 1.393(7) . ? C00O C011 1.497(7) . ? C00O C01G 1.418(7) . ? C00P H00P 0.9300 . ? C00P C015 1.369(7) . ? C00Q C00Z 1.392(7) . ? C00Q C01A 1.402(7) . ? C00R N00V 1.135(6) . ? C00S H00S 0.9300 . ? C00S C01E 1.363(7) . ? C00T H00T 0.9300 . ? C00T C00W 1.370(7) . ? C00U C01R 1.469(9) . ? C00W H00W 0.9300 . ? C00W C010 1.397(8) . ? C00X H00X 0.9300 . ? C00X C01K 1.369(7) . ? C00Y C015 1.388(7) . ? C00Y C01H 1.419(7) . ? C00Z C011 1.515(7) . ? C00Z C01N 1.397(8) . ? C010 C018 1.410(7) . ? C011 C01Q 1.545(8) . ? C011 C01S 1.530(8) . ? C012 C017 1.475(7) . ? C012 C01B 1.369(7) . ? C013 H013 0.9300 . ? C013 C01C 1.387(7) . ? C014 H014 0.9300 . ? C014 C01M 1.398(8) . ? C015 H015 0.9300 . ? C016 H016 0.9300 . ? C016 C01F 1.395(8) . ? C017 C01D 1.382(7) . ? C018 H018 0.9300 . ? C018 C01L 1.376(11) . ? C019 H019 0.9300 . ? C019 C01D 1.355(9) . ? C019 C01F 1.389(9) . ? C01A H01A 0.9300 . ? C01A C01J 1.355(8) . ? C01B H01B 0.9300 . ? C01B C01P 1.362(9) . ? C01C H01C 0.9300 . ? C01C C01O 1.358(8) . ? C01D H01D 0.9300 . ? C01E H01E 0.9300 . ? C01E C01I 1.394(9) . ? C01F H01F 0.9300 . ? C01G H01G 0.9300 . ? C01G C01O 1.360(9) . ? C01H H01H 0.9300 . ? C01H C01I 1.351(8) . ? C01I H01I 0.9300 . ? C01J H01J 0.9300 . ? C01J C01T 1.387(10) . ? C01K H01K 0.9300 . ? C01K C01L 1.376(11) . ? C01L H01L 0.9300 . ? C01M H01M 0.9300 . ? C01M C01P 1.366(9) . ? C01N H01N 0.9300 . ? C01N C01T 1.365(11) . ? C01O H01O 0.9300 . ? C01P H01P 0.9300 . ? C01Q H01Q 0.9600 . ? C01Q H01R 0.9600 . ? C01Q H01S 0.9600 . ? C01R H01X 0.9600 . ? C01R H01Y 0.9600 . ? C01R H 0.9600 . ? C01S H01T 0.9600 . ? C01S H01U 0.9600 . ? C01S H01V 0.9600 . ? C01T H01W 0.9300 . ? C01U H01Z 0.9700 . ? C01U HA 0.9700 . ? C01U C01V 1.418(13) . ? C01V H01 0.9600 . ? C01V HB 0.9600 . ? C01V HC 0.9600 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O001 C007 C008 O002 -1.2(6) . . . . ? O001 C007 C008 C00F -179.5(4) . . . . ? O001 C007 C00A C00E 0.3(6) . . . . ? O001 C007 C00A C00H -179.0(4) . . . . ? O001 C00C C00D C00G -179.4(3) . . . . ? O001 C00C C00D C00N 2.2(5) . . . . ? O001 C00C C00P C015 177.7(4) . . . . ? O002 C008 C00F C00M 178.7(4) . . . . ? O002 C008 C00F C00R 0.3(6) . . . . ? O002 C00B C00N C00D 9.0(5) . . . . ? O002 C00B C00N C00K -176.1(3) . . . . ? O002 C00B C00T C00W 176.2(4) . . . . ? N003 C006 C00O C011 6.0(7) . . . . ? N003 C006 C00O C01G 179.1(4) . . . . ? N003 C006 C013 C01C -179.7(5) . . . . ? N003 C00H C00M N004 -1.8(6) . . . . ? N003 C00H C00M C00F -179.2(4) . . . . ? N003 C00Q C00Z C011 -8.1(7) . . . . ? N003 C00Q C00Z C01N -179.3(5) . . . . ? N003 C00Q C01A C01J 178.3(5) . . . . ? N004 C00I C016 C01F 179.7(5) . . . . ? N004 C00I C017 C012 -0.3(5) . . . . ? N004 C00I C017 C01D -179.2(5) . . . . ? N004 C00L C012 C017 0.3(5) . . . . ? N004 C00L C012 C01B 179.6(5) . . . . ? N004 C00L C014 C01M -179.9(5) . . . . ? C006 N003 C00H C00A -81.0(5) . . . . ? C006 N003 C00H C00M 99.9(5) . . . . ? C006 N003 C00Q C00Z -20.1(6) . . . . ? C006 N003 C00Q C01A 159.8(4) . . . . ? C006 C00O C011 C00Z -30.5(6) . . . . ? C006 C00O C011 C01Q 88.0(6) . . . . ? C006 C00O C011 C01S -153.1(5) . . . . ? C006 C00O C01G C01O 0.1(9) . . . . ? C006 C013 C01C C01O 1.1(9) . . . . ? C007 O001 C00C C00D -95.4(4) . . . . ? C007 O001 C00C C00P 88.2(4) . . . . ? C007 C008 C00F C00M -2.9(6) . . . . ? C007 C008 C00F C00R 178.6(4) . . . . ? C007 C00A C00H N003 -179.8(4) . . . . ? C007 C00A C00H C00M -0.7(6) . . . . ? C008 O002 C00B C00N -97.4(4) . . . . ? C008 O002 C00B C00T 85.7(5) . . . . ? C008 C007 C00A C00E 177.0(4) . . . . ? C008 C007 C00A C00H -2.3(6) . . . . ? C008 C00F C00M N004 -177.4(4) . . . . ? C008 C00F C00M C00H 0.0(6) . . . . ? C00A C007 C008 O002 -177.8(4) . . . . ? C00A C007 C008 C00F 4.0(6) . . . . ? C00A C00H C00M N004 179.1(4) . . . . ? C00A C00H C00M C00F 1.8(6) . . . . ? C00B O002 C008 C007 50.4(5) . . . . ? C00B O002 C008 C00F -131.3(4) . . . . ? C00B C00T C00W C010 0.1(7) . . . . ? C00C O001 C007 C008 54.9(5) . . . . ? C00C O001 C007 C00A -128.5(4) . . . . ? C00C C00D C00G C00S -175.9(4) . . . . ? C00C C00D C00G C00Y 2.8(6) . . . . ? C00C C00D C00N C00B 59.6(5) . . . . ? C00C C00D C00N C00K -115.0(4) . . . . ? C00C C00P C015 C00Y 0.8(8) . . . . ? C00D C00C C00P C015 1.5(7) . . . . ? C00D C00G C00S C01E 179.2(5) . . . . ? C00D C00G C00Y C015 -0.7(7) . . . . ? C00D C00G C00Y C01H -178.8(4) . . . . ? C00E C00A C00H N003 0.9(6) . . . . ? C00E C00A C00H C00M -180.0(4) . . . . ? C00G C00D C00N C00B -118.7(4) . . . . ? C00G C00D C00N C00K 66.7(6) . . . . ? C00G C00S C01E C01I -0.6(9) . . . . ? C00G C00Y C015 C00P -1.1(8) . . . . ? C00G C00Y C01H C01I -0.2(8) . . . . ? C00H N003 C006 C00O -173.3(4) . . . . ? C00H N003 C006 C013 6.4(6) . . . . ? C00H N003 C00Q C00Z 174.9(4) . . . . ? C00H N003 C00Q C01A -5.2(7) . . . . ? C00I N004 C00L C012 -0.5(5) . . . . ? C00I N004 C00L C014 179.8(5) . . . . ? C00I N004 C00M C00F 97.3(5) . . . . ? C00I N004 C00M C00H -80.0(6) . . . . ? C00I C016 C01F C019 0.7(8) . . . . ? C00I C017 C01D C019 -1.1(8) . . . . ? C00K C00X C01K C01L -0.4(8) . . . . ? C00K C010 C018 C01L -0.5(8) . . . . ? C00L N004 C00I C016 179.4(5) . . . . ? C00L N004 C00I C017 0.4(5) . . . . ? C00L N004 C00M C00F -99.9(5) . . . . ? C00L N004 C00M C00H 82.7(6) . . . . ? C00L C012 C017 C00I 0.0(6) . . . . ? C00L C012 C017 C01D 178.8(6) . . . . ? C00L C012 C01B C01P 0.8(9) . . . . ? C00L C014 C01M C01P -0.2(11) . . . . ? C00M N004 C00I C016 -15.3(8) . . . . ? C00M N004 C00I C017 165.8(4) . . . . ? C00M N004 C00L C012 -165.3(4) . . . . ? C00M N004 C00L C014 14.9(8) . . . . ? C00N C00B C00T C00W -0.6(7) . . . . ? C00N C00D C00G C00S 2.4(6) . . . . ? C00N C00D C00G C00Y -179.0(4) . . . . ? C00N C00K C00X C01K 179.4(4) . . . . ? C00N C00K C010 C00W -0.3(6) . . . . ? C00N C00K C010 C018 -179.0(4) . . . . ? C00O C006 C013 C01C 0.0(8) . . . . ? C00O C01G C01O C01C 1.0(11) . . . . ? C00P C00C C00D C00G -3.2(6) . . . . ? C00P C00C C00D C00N 178.4(4) . . . . ? C00Q N003 C006 C00O 21.4(6) . . . . ? C00Q N003 C006 C013 -158.8(5) . . . . ? C00Q N003 C00H C00A 84.2(5) . . . . ? C00Q N003 C00H C00M -94.9(5) . . . . ? C00Q C00Z C011 C00O 31.7(7) . . . . ? C00Q C00Z C011 C01Q -86.5(6) . . . . ? C00Q C00Z C011 C01S 153.6(5) . . . . ? C00Q C00Z C01N C01T -0.1(11) . . . . ? C00Q C01A C01J C01T 1.8(11) . . . . ? C00R C00F C00M N004 1.0(6) . . . . ? C00R C00F C00M C00H 178.4(4) . . . . ? C00S C00G C00Y C015 178.0(5) . . . . ? C00S C00G C00Y C01H -0.1(7) . . . . ? C00S C01E C01I C01H 0.2(10) . . . . ? C00T C00B C00N C00D -174.2(4) . . . . ? C00T C00B C00N C00K 0.7(6) . . . . ? C00T C00W C010 C00K 0.3(7) . . . . ? C00T C00W C010 C018 179.1(5) . . . . ? C00U O005 C01U C01V 107.6(9) . . . . ? C00W C010 C018 C01L -179.2(5) . . . . ? C00X C00K C00N C00B -178.9(4) . . . . ? C00X C00K C00N C00D -4.3(6) . . . . ? C00X C00K C010 C00W 178.4(5) . . . . ? C00X C00K C010 C018 -0.3(7) . . . . ? C00X C01K C01L C018 -0.4(9) . . . . ? C00Y C00G C00S C01E 0.5(7) . . . . ? C00Y C01H C01I C01E 0.2(10) . . . . ? C00Z C00Q C01A C01J -1.7(9) . . . . ? C00Z C01N C01T C01J 0.2(14) . . . . ? C010 C00K C00N C00B -0.2(6) . . . . ? C010 C00K C00N C00D 174.4(4) . . . . ? C010 C00K C00X C01K 0.7(7) . . . . ? C010 C018 C01L C01K 0.8(9) . . . . ? C011 C00O C01G C01O 173.2(6) . . . . ? C011 C00Z C01N C01T -171.2(7) . . . . ? C012 C00L C014 C01M 0.3(9) . . . . ? C012 C017 C01D C019 -179.8(6) . . . . ? C012 C01B C01P C01M -0.7(11) . . . . ? C013 C006 C00O C011 -173.7(5) . . . . ? C013 C006 C00O C01G -0.6(7) . . . . ? C013 C01C C01O C01G -1.6(11) . . . . ? C014 C00L C012 C017 -179.9(5) . . . . ? C014 C00L C012 C01B -0.6(8) . . . . ? C014 C01M C01P C01B 0.5(12) . . . . ? C015 C00Y C01H C01I -178.3(6) . . . . ? C016 C00I C017 C012 -179.3(5) . . . . ? C016 C00I C017 C01D 1.8(8) . . . . ? C017 C00I C016 C01F -1.5(7) . . . . ? C017 C012 C01B C01P 179.9(6) . . . . ? C01A C00Q C00Z C011 172.0(5) . . . . ? C01A C00Q C00Z C01N 0.8(8) . . . . ? C01A C01J C01T C01N -1.1(14) . . . . ? C01B C012 C017 C00I -179.2(6) . . . . ? C01B C012 C017 C01D -0.4(11) . . . . ? C01D C019 C01F C016 -0.1(9) . . . . ? C01F C019 C01D C017 0.3(9) . . . . ? C01G C00O C011 C00Z 156.7(5) . . . . ? C01G C00O C011 C01Q -84.8(6) . . . . ? C01G C00O C011 C01S 34.1(7) . . . . ? C01H C00Y C015 C00P 177.0(5) . . . . ? C01N C00Z C011 C00O -157.5(6) . . . . ? C01N C00Z C011 C01Q 84.3(7) . . . . ? C01N C00Z C011 C01S -35.6(8) . . . . ? C01U O005 C00U O009 -6.8(9) . . . . ? C01U O005 C00U C01R 172.5(7) . . . . ?