#------------------------------------------------------------------------------ #$Date: 2022-03-29 12:03:18 +0300 (Tue, 29 Mar 2022) $ #$Revision: 274087 $ #$URL: file:///home/coder/svn-repositories/cod/cif/8/10/49/8104933.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_8104933 loop_ _publ_author_name 'Wang, Li-Hua' 'Zhou, Xiao-Jing' 'Liu, Li-Li' 'Zhang, Ai-Ling' 'Tai, Xi-Shi' _publ_section_title ; The crystal structure of 5H-dibenzo[b,e]azepine-6,11-dione, C14H9NO2 ; _journal_issue 1 _journal_name_full 'Zeitschrift f\"ur Kristallographie - New Crystal Structures' _journal_page_first 243 _journal_page_last 244 _journal_paper_doi 10.1515/ncrs-2020-0482 _journal_volume 236 _journal_year 2021 _chemical_formula_moiety 'C14 H9 N O2' _chemical_formula_sum 'C14 H9 N O2' _chemical_formula_weight 223.22 _space_group_crystal_system orthorhombic _space_group_IT_number 29 _space_group_name_Hall 'P 2c -2ac' _space_group_name_H-M_alt 'P c a 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 27.190(4) _cell_length_b 4.3317(6) _cell_length_c 17.297(2) _cell_measurement_reflns_used 1636 _cell_measurement_temperature 150.00(10) _cell_measurement_theta_max 26.5710 _cell_measurement_theta_min 2.7710 _cell_volume 2037.2(5) _computing_cell_refinement 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 1.3-alpha (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3-alpha (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 150.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2684 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.868 _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 -8.00 60.00 1.00 5.00 -- -11.27 37.00 150.00 68 2 \w -43.00 14.00 1.00 5.00 -- 11.90 -57.00 0.00 57 ; _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 0.0845409000 _diffrn_orient_matrix_UB_12 -0.0214671000 _diffrn_orient_matrix_UB_13 -0.0097562000 _diffrn_orient_matrix_UB_21 -0.0163009000 _diffrn_orient_matrix_UB_22 -0.0086903000 _diffrn_orient_matrix_UB_23 0.0384633000 _diffrn_orient_matrix_UB_31 -0.1393070000 _diffrn_orient_matrix_UB_32 -0.0119700000 _diffrn_orient_matrix_UB_33 -0.0104490000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_unetI/netI 0.0645 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.868 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 6181 _diffrn_reflns_point_group_measured_fraction_full 0.815 _diffrn_reflns_point_group_measured_fraction_max 0.671 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.331 _diffrn_reflns_theta_min 2.355 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.86525 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.456 _exptl_crystal_description block _exptl_crystal_F_000 928 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.213 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.055 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack -1.1(19) _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 308 _refine_ls_number_reflns 3727 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.020 _refine_ls_R_factor_all 0.0674 _refine_ls_R_factor_gt 0.0524 _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^)+(0.0463P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1030 _refine_ls_wR_factor_ref 0.1122 _reflns_Friedel_coverage 0.501 _reflns_Friedel_fraction_full 0.620 _reflns_Friedel_fraction_max 0.463 _reflns_number_gt 3061 _reflns_number_total 3727 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file suppl_j_ncrs-2020-0482_suppl.cif _cod_data_source_block w02 _cod_database_code 8104933 _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 99.68 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Twinned data refinement Scales: 2.1(19) -1.1(19) 2. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups 3.a Aromatic/amide H refined with riding coordinates: N1(H1), N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C16(H16), C17(H17), C18(H18), C19(H19), C25(H25), C26(H26), C27(H27), C28(H28) ; _shelx_res_file ; TITL w02_a.res in Pca2(1) w02.res created by SHELXL-2018/3 at 17:54:50 on 09-Sep-2020 REM Old TITL w02 in Pbcm REM SHELXT solution in Pca2(1): R1 0.102, Rweak 0.258, Alpha 0.004 REM 0.804 for 346 systematic absences, Orientation a'=b, b'=a, c'=-c REM Flack x = -0.148 ( 1.247 ) from 917 Parsons' quotients REM Formula found by SHELXT: C28 N2 O4 CELL 0.71073 27.1903 4.3317 17.297 90 90 90 ZERR 8 0.004 0.0006 0.0022 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM 0.5+X,-Y,+Z SYMM 0.5-X,+Y,0.5+Z SFAC C H N O UNIT 112 72 8 16 L.S. 20 PLAN 5 CONF BOND list 4 MORE -1 BOND $H fmap 2 53 acta TWIN -1 0 0 0 -1 0 0 0 -1 2 REM REM REM WGHT 0.046300 BASF -1.11893 FVAR 0.66193 O1 4 0.231514 1.123676 0.403722 11.00000 0.01947 0.04304 = 0.03489 -0.00124 -0.00395 -0.00259 O2 4 0.381273 0.675732 0.565479 11.00000 0.02386 0.02317 = 0.02687 0.00549 0.00086 0.00263 O3 4 0.480029 0.834669 0.437079 11.00000 0.01884 0.02863 = 0.02609 0.00470 -0.00113 0.00364 O4 4 0.627375 0.300575 0.602246 11.00000 0.01886 0.05862 = 0.03341 -0.00214 -0.00952 0.00305 N1 3 0.377873 1.000358 0.465596 11.00000 0.01596 0.02171 = 0.02261 0.00033 0.00398 0.00244 AFIX 43 H1 2 0.406255 0.924542 0.454597 11.00000 -1.20000 AFIX 0 N2 3 0.482076 0.500717 0.534632 11.00000 0.01803 0.02180 = 0.02428 0.00120 -0.00044 0.00413 AFIX 43 H2 2 0.453107 0.572572 0.543268 11.00000 -1.20000 AFIX 0 C1 1 0.313135 1.298493 0.396863 11.00000 0.01809 0.01889 = 0.02189 -0.00535 -0.00123 0.00179 C2 1 0.302858 1.504002 0.336337 11.00000 0.02236 0.02519 = 0.02481 -0.00489 -0.00287 0.00487 AFIX 43 H2A 2 0.270285 1.555356 0.326154 11.00000 -1.20000 AFIX 0 C3 1 0.339185 1.631748 0.291678 11.00000 0.03295 0.02289 = 0.02081 -0.00124 0.00143 0.00357 AFIX 43 H3 2 0.331570 1.770661 0.252469 11.00000 -1.20000 AFIX 0 C4 1 0.387492 1.549103 0.306314 11.00000 0.02607 0.02361 = 0.02235 -0.00136 0.00368 -0.00146 AFIX 43 H4 2 0.412527 1.631853 0.276104 11.00000 -1.20000 AFIX 0 C5 1 0.399130 1.345161 0.365227 11.00000 0.01766 0.02114 = 0.02599 -0.00576 0.00485 0.00126 AFIX 43 H5 2 0.431729 1.290081 0.373857 11.00000 -1.20000 AFIX 0 C6 1 0.361919 1.222012 0.411734 11.00000 0.01816 0.01664 = 0.01908 -0.00666 -0.00070 0.00190 C7 1 0.358209 0.879776 0.531274 11.00000 0.01620 0.01941 = 0.02082 -0.00270 -0.00222 -0.00079 C8 1 0.311873 1.000192 0.565192 11.00000 0.01490 0.02010 = 0.02441 -0.00027 0.00057 -0.00134 C9 1 0.308064 0.974339 0.645997 11.00000 0.02336 0.03346 = 0.02480 0.00087 0.00202 0.00207 AFIX 43 H9 2 0.333814 0.886493 0.673718 11.00000 -1.20000 AFIX 0 C10 1 0.266868 1.076715 0.685059 11.00000 0.03434 0.04038 = 0.02645 0.00245 0.00872 0.00169 AFIX 43 H10 2 0.265285 1.063217 0.738662 11.00000 -1.20000 AFIX 0 C11 1 0.228123 1.199104 0.643790 11.00000 0.02628 0.03846 = 0.03483 -0.00158 0.01190 0.00288 AFIX 43 H11 2 0.200338 1.267870 0.669994 11.00000 -1.20000 AFIX 0 C12 1 0.229865 1.221201 0.564588 11.00000 0.01825 0.03036 = 0.03067 -0.00051 0.00280 0.00227 AFIX 43 H12 2 0.203017 1.299076 0.537582 11.00000 -1.20000 AFIX 0 C13 1 0.272207 1.126201 0.524241 11.00000 0.01650 0.02186 = 0.02365 -0.00356 0.00386 -0.00282 C14 1 0.270096 1.166594 0.438472 11.00000 0.01555 0.02079 = 0.02365 -0.00441 -0.00121 0.00239 C15 1 0.552615 0.531364 0.441367 11.00000 0.01834 0.01992 = 0.02320 -0.00556 -0.00065 0.00023 C16 1 0.560897 0.614062 0.364657 11.00000 0.01926 0.02837 = 0.02925 0.00426 -0.00151 0.00237 AFIX 43 H16 2 0.536696 0.721675 0.337875 11.00000 -1.20000 AFIX 0 C17 1 0.604294 0.539699 0.327465 11.00000 0.02426 0.03659 = 0.02675 -0.00305 0.00227 -0.00066 AFIX 43 H17 2 0.609050 0.595254 0.276071 11.00000 -1.20000 AFIX 0 C18 1 0.640799 0.381260 0.367402 11.00000 0.01879 0.04057 = 0.03410 -0.00905 0.00582 0.00284 AFIX 43 H18 2 0.669805 0.325489 0.342568 11.00000 -1.20000 AFIX 0 C19 1 0.633660 0.307722 0.443914 11.00000 0.01864 0.03320 = 0.03386 -0.00322 -0.00353 0.00351 AFIX 43 H19 2 0.658624 0.207849 0.470846 11.00000 -1.20000 AFIX 0 C20 1 0.589775 0.379278 0.482366 11.00000 0.01806 0.02031 = 0.02976 -0.00472 -0.00293 -0.00100 C21 1 0.588915 0.293939 0.566575 11.00000 0.02131 0.02064 = 0.02405 -0.00426 -0.00594 0.00440 C22 1 0.543974 0.177011 0.604566 11.00000 0.02182 0.02105 = 0.01907 -0.00651 -0.00458 0.00361 C23 1 0.496201 0.275623 0.588469 11.00000 0.02286 0.01750 = 0.01866 -0.00435 -0.00281 0.00367 C24 1 0.503835 0.630963 0.471878 11.00000 0.02052 0.01835 = 0.02242 -0.00317 -0.00213 -0.00086 C25 1 0.457037 0.164774 0.634330 11.00000 0.02145 0.02176 = 0.02344 -0.00197 -0.00269 -0.00085 AFIX 43 H25 2 0.425211 0.233391 0.624704 11.00000 -1.20000 AFIX 0 C26 1 0.465265 -0.043594 0.693148 11.00000 0.03060 0.02136 = 0.02244 -0.00086 0.00070 -0.00202 AFIX 43 H26 2 0.439052 -0.115078 0.722685 11.00000 -1.20000 AFIX 0 C27 1 0.512727 -0.147193 0.708411 11.00000 0.03658 0.02145 = 0.02232 0.00185 -0.00683 0.00004 AFIX 43 H27 2 0.518304 -0.290562 0.747461 11.00000 -1.20000 AFIX 0 C28 1 0.551184 -0.036105 0.665395 11.00000 0.02865 0.02168 = 0.02222 -0.00358 -0.00979 0.00521 AFIX 43 H28 2 0.582911 -0.102825 0.676544 11.00000 -1.20000 AFIX 0 HKLF 4 REM w02_a.res in Pca2(1) REM wR2 = 0.1122, GooF = S = 1.021, Restrained GooF = 1.020 for all data REM R1 = 0.0524 for 3061 Fo > 4sig(Fo) and 0.0674 for all 3727 data REM 308 parameters refined using 1 restraints END WGHT 0.0464 0.0000 REM Highest difference peak 0.213, deepest hole -0.262, 1-sigma level 0.055 Q1 1 0.6555 0.0289 0.4680 11.00000 0.05 0.21 Q2 1 0.2785 0.7027 0.5797 11.00000 0.05 0.21 Q3 1 0.5407 -0.3868 0.7604 11.00000 0.05 0.21 Q4 1 0.3420 1.3019 0.4189 11.00000 0.05 0.20 Q5 1 0.4175 0.6669 0.5380 11.00000 0.05 0.19 ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' 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 O1 O 0.23151(10) 1.1237(7) 0.40372(17) 0.0325(7) Uani 1 1 d . . . . . O2 O 0.38127(10) 0.6757(6) 0.56548(15) 0.0246(6) Uani 1 1 d . . . . . O3 O 0.48003(9) 0.8347(6) 0.43708(14) 0.0245(6) Uani 1 1 d . . . . . O4 O 0.62737(10) 0.3006(7) 0.60225(16) 0.0370(8) Uani 1 1 d . . . . . N1 N 0.37787(11) 1.0004(7) 0.46560(18) 0.0201(7) Uani 1 1 d . . . . . H1 H 0.406255 0.924542 0.454597 0.024 Uiso 1 1 calc R U . . . N2 N 0.48208(11) 0.5007(7) 0.53463(17) 0.0214(7) Uani 1 1 d . . . . . H2 H 0.453107 0.572572 0.543268 0.026 Uiso 1 1 calc R U . . . C1 C 0.31314(13) 1.2985(8) 0.3969(2) 0.0196(8) Uani 1 1 d . . . . . C2 C 0.30286(14) 1.5040(9) 0.3363(2) 0.0241(9) Uani 1 1 d . . . . . H2A H 0.270285 1.555356 0.326154 0.029 Uiso 1 1 calc R U . . . C3 C 0.33918(15) 1.6317(9) 0.2917(2) 0.0256(9) Uani 1 1 d . . . . . H3 H 0.331570 1.770661 0.252469 0.031 Uiso 1 1 calc R U . . . C4 C 0.38749(15) 1.5491(9) 0.3063(2) 0.0240(9) Uani 1 1 d . . . . . H4 H 0.412527 1.631853 0.276104 0.029 Uiso 1 1 calc R U . . . C5 C 0.39913(14) 1.3452(9) 0.3652(2) 0.0216(8) Uani 1 1 d . . . . . H5 H 0.431729 1.290081 0.373857 0.026 Uiso 1 1 calc R U . . . C6 C 0.36192(13) 1.2220(8) 0.4117(2) 0.0180(8) Uani 1 1 d . . . . . C7 C 0.35821(13) 0.8798(8) 0.5313(2) 0.0188(8) Uani 1 1 d . . . . . C8 C 0.31187(13) 1.0002(8) 0.5652(2) 0.0198(8) Uani 1 1 d . . . . . C9 C 0.30806(15) 0.9743(9) 0.6460(2) 0.0272(9) Uani 1 1 d . . . . . H9 H 0.333814 0.886493 0.673718 0.033 Uiso 1 1 calc R U . . . C10 C 0.26687(15) 1.0767(10) 0.6851(2) 0.0337(11) Uani 1 1 d . . . . . H10 H 0.265285 1.063217 0.738662 0.040 Uiso 1 1 calc R U . . . C11 C 0.22812(16) 1.1991(10) 0.6438(2) 0.0332(10) Uani 1 1 d . . . . . H11 H 0.200338 1.267870 0.669994 0.040 Uiso 1 1 calc R U . . . C12 C 0.22986(14) 1.2212(9) 0.5646(2) 0.0264(9) Uani 1 1 d . . . . . H12 H 0.203017 1.299076 0.537582 0.032 Uiso 1 1 calc R U . . . C13 C 0.27221(13) 1.1262(9) 0.5242(2) 0.0207(8) Uani 1 1 d . . . . . C14 C 0.27010(13) 1.1666(9) 0.4385(2) 0.0200(8) Uani 1 1 d . . . . . C15 C 0.55262(13) 0.5314(8) 0.4414(2) 0.0205(8) Uani 1 1 d . . . . . C16 C 0.56090(14) 0.6141(9) 0.3647(2) 0.0256(9) Uani 1 1 d . . . . . H16 H 0.536696 0.721675 0.337875 0.031 Uiso 1 1 calc R U . . . C17 C 0.60429(14) 0.5397(10) 0.3275(2) 0.0292(10) Uani 1 1 d . . . . . H17 H 0.609050 0.595254 0.276071 0.035 Uiso 1 1 calc R U . . . C18 C 0.64080(15) 0.3813(10) 0.3674(2) 0.0312(10) Uani 1 1 d . . . . . H18 H 0.669805 0.325489 0.342568 0.037 Uiso 1 1 calc R U . . . C19 C 0.63366(15) 0.3077(9) 0.4439(2) 0.0286(10) Uani 1 1 d . . . . . H19 H 0.658624 0.207849 0.470846 0.034 Uiso 1 1 calc R U . . . C20 C 0.58978(13) 0.3793(8) 0.4824(2) 0.0227(8) Uani 1 1 d . . . . . C21 C 0.58892(14) 0.2939(8) 0.5666(2) 0.0220(8) Uani 1 1 d . . . . . C22 C 0.54397(14) 0.1770(8) 0.6046(2) 0.0206(8) Uani 1 1 d . . . . . C23 C 0.49620(14) 0.2756(8) 0.5885(2) 0.0197(8) Uani 1 1 d . . . . . C24 C 0.50384(13) 0.6310(9) 0.4719(2) 0.0204(8) Uani 1 1 d . . . . . C25 C 0.45704(14) 0.1648(8) 0.6343(2) 0.0222(9) Uani 1 1 d . . . . . H25 H 0.425211 0.233391 0.624704 0.027 Uiso 1 1 calc R U . . . C26 C 0.46526(15) -0.0436(9) 0.6931(2) 0.0248(9) Uani 1 1 d . . . . . H26 H 0.439052 -0.115078 0.722685 0.030 Uiso 1 1 calc R U . . . C27 C 0.51273(16) -0.1472(8) 0.7084(2) 0.0268(9) Uani 1 1 d . . . . . H27 H 0.518304 -0.290562 0.747461 0.032 Uiso 1 1 calc R U . . . C28 C 0.55118(16) -0.0361(9) 0.6654(2) 0.0242(9) Uani 1 1 d . . . . . H28 H 0.582911 -0.102825 0.676544 0.029 Uiso 1 1 calc R U . . . 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 O1 0.0195(15) 0.0430(18) 0.0349(16) -0.0012(14) -0.0039(13) -0.0026(13) O2 0.0239(15) 0.0232(14) 0.0269(15) 0.0055(12) 0.0009(12) 0.0026(12) O3 0.0188(14) 0.0286(15) 0.0261(14) 0.0047(13) -0.0011(12) 0.0036(12) O4 0.0189(14) 0.059(2) 0.0334(16) -0.0021(15) -0.0095(13) 0.0030(14) N1 0.0160(16) 0.0217(16) 0.0226(16) 0.0003(14) 0.0040(14) 0.0024(13) N2 0.0180(16) 0.0218(16) 0.0243(17) 0.0012(14) -0.0004(13) 0.0041(13) C1 0.0181(19) 0.0189(19) 0.0219(19) -0.0053(16) -0.0012(16) 0.0018(15) C2 0.022(2) 0.025(2) 0.025(2) -0.0049(17) -0.0029(17) 0.0049(17) C3 0.033(2) 0.023(2) 0.021(2) -0.0012(17) 0.0014(18) 0.0036(18) C4 0.026(2) 0.024(2) 0.022(2) -0.0014(19) 0.0037(17) -0.0015(17) C5 0.0177(19) 0.0211(19) 0.0260(19) -0.0058(17) 0.0048(16) 0.0013(15) C6 0.0182(19) 0.0166(18) 0.0191(18) -0.0067(15) -0.0007(15) 0.0019(15) C7 0.0162(18) 0.0194(18) 0.0208(19) -0.0027(17) -0.0022(15) -0.0008(15) C8 0.0149(18) 0.0201(19) 0.0244(19) -0.0003(16) 0.0006(16) -0.0013(16) C9 0.023(2) 0.033(2) 0.025(2) 0.0009(19) 0.0020(17) 0.0021(19) C10 0.034(3) 0.040(2) 0.026(2) 0.002(2) 0.0087(19) 0.002(2) C11 0.026(2) 0.038(2) 0.035(2) -0.002(2) 0.0119(19) 0.0029(19) C12 0.018(2) 0.030(2) 0.031(2) -0.0005(19) 0.0028(17) 0.0023(17) C13 0.0165(19) 0.0219(19) 0.024(2) -0.0036(17) 0.0039(16) -0.0028(16) C14 0.0155(19) 0.021(2) 0.024(2) -0.0044(17) -0.0012(16) 0.0024(15) C15 0.0183(19) 0.0199(18) 0.023(2) -0.0056(17) -0.0007(15) 0.0002(15) C16 0.019(2) 0.028(2) 0.029(2) 0.0043(19) -0.0015(17) 0.0024(16) C17 0.024(2) 0.037(2) 0.027(2) -0.0030(19) 0.0023(18) -0.0007(19) C18 0.019(2) 0.041(2) 0.034(2) -0.009(2) 0.0058(18) 0.0028(19) C19 0.019(2) 0.033(2) 0.034(2) -0.003(2) -0.0035(17) 0.0035(17) C20 0.0181(19) 0.0203(19) 0.030(2) -0.0047(17) -0.0029(17) -0.0010(16) C21 0.021(2) 0.0206(18) 0.0240(19) -0.0043(17) -0.0059(17) 0.0044(16) C22 0.0218(19) 0.0210(19) 0.0191(18) -0.0065(17) -0.0046(16) 0.0036(15) C23 0.023(2) 0.0175(18) 0.0187(19) -0.0043(16) -0.0028(15) 0.0037(16) C24 0.0205(19) 0.0184(18) 0.022(2) -0.0032(17) -0.0021(16) -0.0009(16) C25 0.021(2) 0.022(2) 0.023(2) -0.0020(17) -0.0027(16) -0.0009(16) C26 0.031(2) 0.0214(19) 0.022(2) -0.0009(18) 0.0007(17) -0.0020(17) C27 0.037(2) 0.021(2) 0.022(2) 0.0018(18) -0.0068(17) 0.0000(18) C28 0.029(2) 0.0217(19) 0.022(2) -0.0036(18) -0.0098(17) 0.0052(17) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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 C6 N1 H1 113.0 . . C7 N1 H1 113.0 . . C7 N1 C6 134.0(3) . . C23 N2 H2 112.8 . . C24 N2 H2 112.8 . . C24 N2 C23 134.4(3) . . C2 C1 C14 116.6(3) . . C6 C1 C2 118.6(3) . . C6 C1 C14 124.7(3) . . C1 C2 H2A 118.9 . . C3 C2 C1 122.2(4) . . C3 C2 H2A 118.9 . . C2 C3 H3 120.8 . . C2 C3 C4 118.4(4) . . C4 C3 H3 120.8 . . C3 C4 H4 119.5 . . C3 C4 C5 121.1(4) . . C5 C4 H4 119.5 . . C4 C5 H5 120.0 . . C4 C5 C6 120.1(4) . . C6 C5 H5 120.0 . . C1 C6 N1 125.4(3) . . C1 C6 C5 119.5(3) . . C5 C6 N1 114.7(3) . . O2 C7 N1 118.4(3) . . O2 C7 C8 119.6(3) . . N1 C7 C8 121.9(3) . . C9 C8 C7 115.3(3) . . C13 C8 C7 126.2(3) . . C13 C8 C9 118.5(4) . . C8 C9 H9 119.3 . . C10 C9 C8 121.4(4) . . C10 C9 H9 119.3 . . C9 C10 H10 120.3 . . C11 C10 C9 119.3(4) . . C11 C10 H10 120.3 . . C10 C11 H11 119.4 . . C12 C11 C10 121.1(4) . . C12 C11 H11 119.4 . . C11 C12 H12 119.9 . . C11 C12 C13 120.1(4) . . C13 C12 H12 119.9 . . C8 C13 C12 119.5(3) . . C8 C13 C14 125.2(3) . . C12 C13 C14 115.2(3) . . O1 C14 C1 119.7(4) . . O1 C14 C13 120.2(4) . . C1 C14 C13 119.7(3) . . C16 C15 C20 119.2(3) . . C16 C15 C24 114.0(3) . . C20 C15 C24 126.8(3) . . C15 C16 H16 119.3 . . C17 C16 C15 121.4(4) . . C17 C16 H16 119.3 . . C16 C17 H17 120.2 . . C16 C17 C18 119.6(4) . . C18 C17 H17 120.2 . . C17 C18 H18 120.3 . . C19 C18 C17 119.5(4) . . C19 C18 H18 120.3 . . C18 C19 H19 119.1 . . C18 C19 C20 121.7(4) . . C20 C19 H19 119.1 . . C15 C20 C19 118.6(4) . . C15 C20 C21 126.6(3) . . C19 C20 C21 114.8(3) . . O4 C21 C20 118.2(4) . . O4 C21 C22 119.6(4) . . C22 C21 C20 121.9(3) . . C23 C22 C21 125.2(3) . . C23 C22 C28 118.5(4) . . C28 C22 C21 116.1(3) . . N2 C23 C25 113.8(3) . . C22 C23 N2 126.9(4) . . C22 C23 C25 119.1(3) . . O3 C24 N2 116.9(3) . . O3 C24 C15 119.7(3) . . N2 C24 C15 123.4(3) . . C23 C25 H25 119.5 . . C26 C25 C23 121.0(4) . . C26 C25 H25 119.5 . . C25 C26 H26 119.9 . . C25 C26 C27 120.1(4) . . C27 C26 H26 119.9 . . C26 C27 H27 120.3 . . C28 C27 C26 119.4(4) . . C28 C27 H27 120.3 . . C22 C28 H28 119.1 . . C27 C28 C22 121.8(4) . . C27 C28 H28 119.1 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O1 C14 1.223(4) . O2 C7 1.235(4) . O3 C24 1.249(4) . O4 C21 1.215(4) . N1 H1 0.8600 . N1 C6 1.406(5) . N1 C7 1.360(5) . N2 H2 0.8600 . N2 C23 1.402(5) . N2 C24 1.359(5) . C1 C2 1.402(5) . C1 C6 1.391(5) . C1 C14 1.488(5) . C2 H2A 0.9300 . C2 C3 1.371(5) . C3 H3 0.9300 . C3 C4 1.385(5) . C4 H4 0.9300 . C4 C5 1.385(5) . C5 H5 0.9300 . C5 C6 1.398(5) . C7 C8 1.484(5) . C8 C9 1.406(5) . C8 C13 1.401(5) . C9 H9 0.9300 . C9 C10 1.381(5) . C10 H10 0.9300 . C10 C11 1.379(6) . C11 H11 0.9300 . C11 C12 1.374(5) . C12 H12 0.9300 . C12 C13 1.408(5) . C13 C14 1.495(5) . C15 C16 1.393(5) . C15 C20 1.399(5) . C15 C24 1.491(5) . C16 H16 0.9300 . C16 C17 1.382(5) . C17 H17 0.9300 . C17 C18 1.390(6) . C18 H18 0.9300 . C18 C19 1.375(6) . C19 H19 0.9300 . C19 C20 1.401(5) . C20 C21 1.503(5) . C21 C22 1.477(5) . C22 C23 1.395(5) . C22 C28 1.413(5) . C23 C25 1.412(5) . C25 H25 0.9300 . C25 C26 1.378(5) . C26 H26 0.9300 . C26 C27 1.392(6) . C27 H27 0.9300 . C27 C28 1.371(6) . C28 H28 0.9300 . 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 O2 C7 C8 C9 26.0(5) . . . . O2 C7 C8 C13 -152.2(4) . . . . O4 C21 C22 C23 149.3(4) . . . . O4 C21 C22 C28 -26.2(5) . . . . N1 C7 C8 C9 -149.9(3) . . . . N1 C7 C8 C13 31.9(5) . . . . N2 C23 C25 C26 -176.1(3) . . . . C1 C2 C3 C4 1.3(6) . . . . C2 C1 C6 N1 -174.2(3) . . . . C2 C1 C6 C5 -1.5(5) . . . . C2 C1 C14 O1 31.4(5) . . . . C2 C1 C14 C13 -140.7(4) . . . . C2 C3 C4 C5 -0.8(6) . . . . C3 C4 C5 C6 -0.8(6) . . . . C4 C5 C6 N1 175.4(3) . . . . C4 C5 C6 C1 2.0(6) . . . . C6 N1 C7 O2 177.7(4) . . . . C6 N1 C7 C8 -6.3(6) . . . . C6 C1 C2 C3 -0.1(6) . . . . C6 C1 C14 O1 -145.8(4) . . . . C6 C1 C14 C13 42.2(5) . . . . C7 N1 C6 C1 -25.1(6) . . . . C7 N1 C6 C5 161.8(4) . . . . C7 C8 C9 C10 -179.9(4) . . . . C7 C8 C13 C12 177.8(4) . . . . C7 C8 C13 C14 -1.2(6) . . . . C8 C9 C10 C11 1.8(7) . . . . C8 C13 C14 O1 142.4(4) . . . . C8 C13 C14 C1 -45.6(5) . . . . C9 C8 C13 C12 -0.3(5) . . . . C9 C8 C13 C14 -179.3(4) . . . . C9 C10 C11 C12 -0.1(7) . . . . C10 C11 C12 C13 -1.8(7) . . . . C11 C12 C13 C8 2.0(6) . . . . C11 C12 C13 C14 -178.9(4) . . . . C12 C13 C14 O1 -36.6(5) . . . . C12 C13 C14 C1 135.4(4) . . . . C13 C8 C9 C10 -1.5(6) . . . . C14 C1 C2 C3 -177.4(3) . . . . C14 C1 C6 N1 2.9(6) . . . . C14 C1 C6 C5 175.6(3) . . . . C15 C16 C17 C18 -0.6(6) . . . . C15 C20 C21 O4 -145.9(4) . . . . C15 C20 C21 C22 39.6(5) . . . . C16 C15 C20 C19 -1.8(5) . . . . C16 C15 C20 C21 175.1(4) . . . . C16 C15 C24 O3 -17.2(5) . . . . C16 C15 C24 N2 159.5(3) . . . . C16 C17 C18 C19 -1.6(6) . . . . C17 C18 C19 C20 2.1(6) . . . . C18 C19 C20 C15 -0.4(6) . . . . C18 C19 C20 C21 -177.7(4) . . . . C19 C20 C21 O4 31.1(5) . . . . C19 C20 C21 C22 -143.4(4) . . . . C20 C15 C16 C17 2.3(6) . . . . C20 C15 C24 O3 160.2(4) . . . . C20 C15 C24 N2 -23.1(6) . . . . C20 C21 C22 C23 -36.4(5) . . . . C20 C21 C22 C28 148.1(3) . . . . C21 C22 C23 N2 -0.4(6) . . . . C21 C22 C23 C25 -174.1(3) . . . . C21 C22 C28 C27 175.9(3) . . . . C22 C23 C25 C26 -1.5(5) . . . . C23 N2 C24 O3 -178.8(4) . . . . C23 N2 C24 C15 4.4(6) . . . . C23 C22 C28 C27 0.1(6) . . . . C23 C25 C26 C27 0.3(5) . . . . C24 N2 C23 C22 19.2(6) . . . . C24 N2 C23 C25 -166.8(4) . . . . C24 C15 C16 C17 180.0(4) . . . . C24 C15 C20 C19 -179.1(4) . . . . C24 C15 C20 C21 -2.2(6) . . . . C25 C26 C27 C28 1.1(6) . . . . C26 C27 C28 C22 -1.3(6) . . . . C28 C22 C23 N2 175.1(3) . . . . C28 C22 C23 C25 1.3(5) . . . .