#------------------------------------------------------------------------------ #$Date: 2019-02-23 01:25:20 +0200 (Sat, 23 Feb 2019) $ #$Revision: 213800 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/06/1550644.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_1550644 loop_ _publ_author_name 'Xu, Wenhan' 'Lee, Michelle M. S.' 'Zhang, Zhihan' 'Sung, Herman H-Y.' 'Williams, Ian Duncan' 'Kwok, Ryan T. K.' 'Lam, Jacky Wing Yip' 'Wang, Dong' 'Tang, Ben Zhong' _publ_section_title ; Facile synthesis of AIEgens with wide color tunability for cellular imaging and therapy ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C8SC05805A _journal_year 2019 _chemical_formula_moiety 'C25 H21 N O3 S' _chemical_formula_sum 'C25 H21 N O3 S' _chemical_formula_weight 415.49 _chemical_name_systematic ; ? ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2018-01-30 _audit_creation_method ; Olex2 1.2 (compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381) ; _audit_update_record ; 2018-12-22 deposited with the CCDC. 2019-02-19 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 107.5934(19) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.89163(18) _cell_length_b 19.5816(3) _cell_length_c 10.94012(19) _cell_measurement_reflns_used 6303 _cell_measurement_temperature 100.01(10) _cell_measurement_theta_max 74.0830 _cell_measurement_theta_min 4.5180 _cell_volume 2019.92(6) _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (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 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.01(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.3577 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _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 80.00 174.00 1.00 5.00 -- 107.97 30.00 90.00 94 2 \w -67.00 28.00 1.00 2.00 -- -40.45 37.00 90.00 95 3 \w -96.00 -3.00 1.00 2.00 -- -40.45 125.00 150.00 93 4 \w -113.00 -16.00 1.00 2.00 -- -40.45 -37.00 -90.00 97 5 \w 54.00 108.00 1.00 5.00 -- 107.97 -94.00 150.00 54 6 \w 50.00 136.00 1.00 5.00 -- 107.97 -45.00 120.00 86 7 \w 44.00 131.00 1.00 5.00 -- 107.97 -45.00 30.00 87 8 \w 40.00 132.00 1.00 5.00 -- 107.97 -61.00 -90.00 92 9 \w 79.00 169.00 1.00 5.00 -- 107.97 -15.00-150.00 90 10 \w 38.00 116.00 1.00 5.00 -- 107.97-111.00 -60.00 78 11 \w 25.00 105.00 1.00 5.00 -- 107.97 -94.00 60.00 80 12 \w 25.00 51.00 1.00 5.00 -- 107.97 -94.00 150.00 26 ; _diffrn_measurement_device 'kappa diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.1396902000 _diffrn_orient_matrix_UB_12 0.0181188000 _diffrn_orient_matrix_UB_13 0.1038329000 _diffrn_orient_matrix_UB_21 0.0445906000 _diffrn_orient_matrix_UB_22 -0.0756606000 _diffrn_orient_matrix_UB_23 0.0086556000 _diffrn_orient_matrix_UB_31 0.0722740000 _diffrn_orient_matrix_UB_32 0.0117408000 _diffrn_orient_matrix_UB_33 -0.1046688000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_unetI/netI 0.0228 _diffrn_reflns_Laue_measured_fraction_full 0.992 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 11028 _diffrn_reflns_point_group_measured_fraction_full 0.992 _diffrn_reflns_point_group_measured_fraction_max 0.992 _diffrn_reflns_theta_full 66.500 _diffrn_reflns_theta_max 67.471 _diffrn_reflns_theta_min 4.516 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_current 0.80 _diffrn_source_power 0.040 _diffrn_source_target Cu _diffrn_source_type 'SuperNova (Cu) X-ray Source' _diffrn_source_voltage 50 _exptl_absorpt_coefficient_mu 1.647 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.94429 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (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 1.366 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 872 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.249 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.037 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 390 _refine_ls_number_reflns 3611 _refine_ls_number_restraints 240 _refine_ls_restrained_S_all 1.021 _refine_ls_R_factor_all 0.0363 _refine_ls_R_factor_gt 0.0325 _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^)+(0.0580P)^2^+0.3490P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0886 _refine_ls_wR_factor_ref 0.0919 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3241 _reflns_number_total 3611 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; dw20a.res created by SHELXL-2014/7 TITL dw20a in P21/n #14 REM reset to P21/n #14 CELL 1.54184 9.89163 19.58165 10.94012 90 107.5934 90 ZERR 4 0.00018 0.00032 0.00019 0 0.0019 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O S UNIT 100 84 4 12 4 SADI C11 C12 C16 C11 C15 C16 C15 C14 C13 C14 C12 C13 SADI C11A C12A C16A C11A C15A C16A C15A C14A C12A C13A C13A C14A SADI S1 C4 S1 C1 S1A C1A S1A C4A RIGU 0.001 0.001 S1 C2 C15 C14 C13 C1 C11 C16 O1 C12 C4 C3 C5 RIGU 0.001 0.001 S1A C2A C1A C4A C3A O1A C5A C11A C12A C15A C16A C14A C13A ISOR 0.005 0.002 O1A O1 L.S. 6 PLAN 20 BOND CONF fmap 2 acta 133 OMIT 0 135 OMIT 0 6 3 OMIT -2 4 4 OMIT -2 4 3 OMIT 1 7 1 OMIT -1 4 2 OMIT 3 6 2 OMIT 1 0 5 OMIT 1 1 2 OMIT 0 9 2 OMIT -4 0 4 OMIT 1 8 2 OMIT -3 1 4 OMIT -8 15 7 OMIT 1 6 0 OMIT -1 1 2 OMIT -2 7 4 OMIT 4 0 0 OMIT -5 1 2 OMIT -3 0 3 OMIT -2 9 2 OMIT -5 6 1 OMIT -1 2 1 OMIT 2 5 4 OMIT 1 0 3 OMIT -3 18 8 OMIT 5 6 0 REM REM REM WGHT 0.058000 0.349000 FVAR 4.71077 PART 1 S1 5 0.218902 0.526754 -0.135811 10.70000 0.02508 0.02173 = 0.02342 0.00067 0.00132 -0.00224 PART 0 PART 2 S1A 5 0.197953 0.464582 0.050931 10.30000 0.03282 0.02985 = 0.03122 0.00313 0.01233 -0.00008 PART 0 PART 1 O1 4 -0.012945 0.462168 -0.360166 10.70000 0.03557 0.04377 = 0.03847 -0.01000 0.00090 0.00425 PART 0 PART 2 O1A 4 -0.106353 0.380957 -0.228893 10.30000 0.04297 0.04323 = 0.04816 -0.00279 0.00773 -0.00087 PART 0 O2 4 0.934210 0.919062 0.095969 11.00000 0.03764 0.02321 = 0.04859 0.00305 0.02048 -0.00490 O3 4 0.882729 0.687677 0.837286 11.00000 0.04493 0.03121 = 0.02737 -0.00029 0.01320 0.00183 N1 3 0.744496 0.690555 0.303021 11.00000 0.03136 0.02271 = 0.02766 -0.00004 0.01040 -0.00409 PART 1 C1 1 0.291774 0.519439 0.030351 10.70000 0.02305 0.02044 = 0.02486 -0.00094 0.00473 0.00377 C2 1 0.229314 0.469689 0.082836 10.70000 0.03240 0.03204 = 0.03505 -0.00136 0.00622 -0.00493 AFIX 43 H2 2 0.255978 0.458624 0.169533 10.70000 -1.20000 AFIX 0 C3 1 0.115898 0.436626 -0.015306 10.70000 0.02144 0.02144 = 0.03022 -0.00314 0.00494 -0.00335 AFIX 43 H3 2 0.060047 0.402020 0.002181 10.70000 -1.20000 AFIX 0 C4 1 0.098843 0.461288 -0.136500 10.70000 0.02218 0.02007 = 0.03072 -0.00150 0.00709 -0.00177 C5 1 -0.001080 0.438926 -0.254652 10.70000 0.02477 0.02772 = 0.03982 -0.01026 0.00181 0.00193 AFIX 43 H5 2 -0.061949 0.403543 -0.249756 10.70000 -1.20000 AFIX 0 C11 1 0.407930 0.563374 0.098811 10.70000 0.02193 0.01818 = 0.02300 0.00127 0.00745 0.00298 C12 1 0.489740 0.599151 0.035487 10.70000 0.02502 0.01925 = 0.02458 -0.00065 0.00784 0.00108 AFIX 43 H12 2 0.466599 0.594716 -0.053091 10.70000 -1.20000 AFIX 0 C13 1 0.603463 0.640877 0.097475 10.70000 0.02456 0.01686 = 0.02627 0.00133 0.00959 0.00072 AFIX 43 H13 2 0.656900 0.662658 0.052201 10.70000 -1.20000 AFIX 0 C14 1 0.635100 0.649091 0.230851 10.70000 0.02199 0.01668 = 0.02782 0.00111 0.01035 0.00055 C15 1 0.554243 0.613737 0.297789 10.70000 0.02249 0.01924 = 0.02481 -0.00065 0.00715 -0.00158 AFIX 43 H15 2 0.575477 0.618974 0.386076 10.70000 -1.20000 AFIX 0 C16 1 0.443359 0.571270 0.232208 10.70000 0.02428 0.02175 = 0.02104 0.00125 0.00803 -0.00179 AFIX 43 H16 2 0.392028 0.547800 0.277379 10.70000 -1.20000 AFIX 0 PART 0 PART 2 C1A 1 0.283472 0.524432 -0.009030 10.30000 0.02975 0.02316 = 0.03584 0.00277 0.01454 0.00340 C2A 1 0.217159 0.525699 -0.132167 10.30000 0.02508 0.02264 = 0.03422 0.00064 0.01465 0.01304 AFIX 43 H2A 2 0.242362 0.559186 -0.181511 10.30000 -1.20000 AFIX 0 C3A 1 0.116831 0.482250 -0.190066 10.30000 0.03964 0.03859 = 0.04058 0.00021 0.01105 -0.00024 AFIX 43 H3A 2 0.074617 0.478046 -0.278062 10.30000 -1.20000 AFIX 0 C4A 1 0.086524 0.444866 -0.097899 10.30000 0.03337 0.03138 = 0.03786 -0.00061 0.01071 0.00364 C5A 1 -0.030007 0.395661 -0.122437 10.30000 0.03880 0.03899 = 0.04681 0.00025 0.00955 -0.00250 AFIX 43 H5A 2 -0.046652 0.374361 -0.052374 10.30000 -1.20000 AFIX 0 C11A 1 0.406833 0.564682 0.072923 10.30000 0.03121 0.02242 = 0.03404 0.00469 0.01467 0.00273 C12A 1 0.499433 0.600708 0.022660 10.30000 0.03031 0.02247 = 0.03683 0.00592 0.01626 0.00233 AFIX 43 H12A 2 0.493398 0.598459 -0.063743 10.30000 -1.20000 AFIX 0 C13A 1 0.601414 0.640227 0.109262 10.30000 0.03139 0.02486 = 0.03841 0.00437 0.01744 -0.00024 AFIX 43 H13A 2 0.659739 0.665685 0.073986 10.30000 -1.20000 AFIX 0 C14A 1 0.628362 0.647037 0.239960 10.30000 0.02803 0.02156 = 0.03720 0.00424 0.01531 0.00266 C15A 1 0.535864 0.607613 0.284710 10.30000 0.03224 0.02819 = 0.03618 0.00297 0.01632 -0.00268 AFIX 43 H15A 2 0.545348 0.607262 0.371914 10.30000 -1.20000 AFIX 0 C16A 1 0.430828 0.569224 0.202227 10.30000 0.02990 0.02280 = 0.03555 0.00448 0.01517 -0.00061 AFIX 43 H16A 2 0.371478 0.544405 0.237352 10.30000 -1.20000 AFIX 0 PART 0 C20 1 0.832201 0.965911 0.020914 11.00000 0.04817 0.02497 = 0.04866 0.00484 0.02349 -0.00265 AFIX 137 H20A 2 0.772517 0.942946 -0.053401 11.00000 -1.50000 H20B 2 0.880152 1.003086 -0.005535 11.00000 -1.50000 H20C 2 0.775255 0.983241 0.071146 11.00000 -1.50000 AFIX 0 C21 1 0.788684 0.748024 0.244058 11.00000 0.02892 0.02081 = 0.02713 -0.00261 0.01255 -0.00259 C22 1 0.691603 0.790410 0.159375 11.00000 0.02525 0.02297 = 0.03440 -0.00180 0.01302 -0.00113 AFIX 43 H22 2 0.595383 0.780237 0.137263 11.00000 -1.20000 AFIX 0 C23 1 0.735965 0.847667 0.107297 11.00000 0.02926 0.02198 = 0.03358 0.00068 0.01271 0.00205 AFIX 43 H23 2 0.669893 0.875283 0.049996 11.00000 -1.20000 AFIX 0 C24 1 0.879889 0.863661 0.141142 11.00000 0.03357 0.02066 = 0.03440 -0.00479 0.01791 -0.00401 C25 1 0.977957 0.821524 0.226307 11.00000 0.02534 0.02805 = 0.03458 -0.00494 0.01199 -0.00483 AFIX 43 H25 2 1.074086 0.831999 0.249318 11.00000 -1.20000 AFIX 0 C26 1 0.932654 0.764055 0.276812 11.00000 0.02816 0.02571 = 0.02990 -0.00176 0.00930 0.00078 AFIX 43 H26 2 0.998768 0.735964 0.332978 11.00000 -1.20000 AFIX 0 C30 1 0.859263 0.745956 0.906467 11.00000 0.04094 0.03235 = 0.03068 -0.00550 0.01497 -0.00578 AFIX 137 H30A 2 0.760980 0.758610 0.876147 11.00000 -1.50000 H30B 2 0.916482 0.783256 0.893628 11.00000 -1.50000 H30C 2 0.884535 0.735220 0.996177 11.00000 -1.50000 AFIX 0 C31 1 0.781903 0.691853 0.440517 11.00000 0.02565 0.02436 = 0.02794 0.00020 0.01077 -0.00287 C32 1 0.760378 0.750212 0.503991 11.00000 0.02843 0.02234 = 0.03376 0.00318 0.01200 0.00150 AFIX 43 H32 2 0.722902 0.789076 0.457088 11.00000 -1.20000 AFIX 0 C33 1 0.794169 0.751320 0.636986 11.00000 0.02990 0.02295 = 0.03367 -0.00360 0.01503 -0.00049 AFIX 43 H33 2 0.781199 0.790961 0.678905 11.00000 -1.20000 AFIX 0 C34 1 0.847406 0.692821 0.706731 11.00000 0.02560 0.02773 = 0.02891 -0.00060 0.01127 -0.00303 C35 1 0.869854 0.633930 0.643422 11.00000 0.02668 0.02287 = 0.03241 0.00269 0.00920 0.00000 AFIX 43 H35 2 0.905723 0.594780 0.690107 11.00000 -1.20000 AFIX 0 C36 1 0.838825 0.633802 0.511579 11.00000 0.02687 0.02187 = 0.03276 -0.00238 0.01167 -0.00073 AFIX 43 H36 2 0.855934 0.594846 0.469917 11.00000 -1.20000 AFIX 0 HKLF 4 REM dw20a in P21/n #14 REM R1 = 0.0325 for 3241 Fo > 4sig(Fo) and 0.0363 for all 3611 data REM 390 parameters refined using 240 restraints END WGHT 0.0515 0.3031 REM Highest difference peak 0.249, deepest hole -0.332, 1-sigma level 0.037 Q1 1 0.0729 0.3975 0.0832 11.00000 0.05 0.25 Q2 1 -0.0126 0.4406 -0.3241 11.00000 0.05 0.18 Q3 1 0.0350 0.4513 -0.2000 11.00000 0.05 0.18 Q4 1 0.8105 0.8445 0.0996 11.00000 0.05 0.16 Q5 1 0.9254 0.8329 0.1565 11.00000 0.05 0.16 Q6 1 0.8749 0.9260 0.0394 11.00000 0.05 0.15 Q7 1 -0.0911 0.3915 -0.3047 11.00000 0.05 0.15 Q8 1 0.0144 0.4808 -0.3788 11.00000 0.05 0.14 Q9 1 0.3446 0.5363 0.0566 11.00000 0.05 0.14 Q10 1 0.7613 0.6564 0.4683 11.00000 0.05 0.14 Q11 1 0.8531 0.7477 0.2417 11.00000 0.05 0.14 Q12 1 0.7558 0.6903 0.3629 11.00000 0.05 0.13 Q13 1 0.6586 0.6879 0.2636 11.00000 0.05 0.13 Q14 1 0.8209 0.6270 0.5745 11.00000 0.05 0.13 Q15 1 0.7448 0.7592 0.1776 11.00000 0.05 0.13 Q16 1 0.7764 0.7167 0.6676 11.00000 0.05 0.12 Q17 1 0.7983 0.7486 0.5741 11.00000 0.05 0.12 Q18 1 0.8480 0.6677 0.4789 11.00000 0.05 0.12 Q19 1 0.2737 0.5251 -0.1586 11.00000 0.05 0.12 Q20 1 0.7368 0.7749 0.2181 11.00000 0.05 0.12 REM The information below was added by Olex2. REM REM R1 = 0.0325 for 3241 Fo > 4sig(Fo) and 0.0363 for all 12010 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.25, deepest hole -0.33 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0363 REM R1_gt = 0.0325 REM wR_ref = 0.0919 REM GOOF = 1.007 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 12010 REM Reflections_gt = 3241 REM Parameters = n/a REM Hole = -0.33 REM Peak = 0.25 REM Flack = n/a ; _cod_data_source_file c8sc05805a2.cif _cod_data_source_block dw20a _cod_database_code 1550644 _shelx_shelxl_version_number 2014/7 _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 99.87 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 67.46 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances C11-C12 \\sim C16-C11 \\sim C15-C16 \\sim C15-C14 \\sim C13-C14 \\sim C12-C13 with sigma of 0.02 C11A-C12A \\sim C16A-C11A \\sim C15A-C16A \\sim C15A-C14A \\sim C12A-C13A \\sim C13A-C14A with sigma of 0.02 S1-C4 \\sim S1-C1 \\sim S1A-C1A \\sim S1A-C4A with sigma of 0.02 3. Uiso/Uaniso restraints and constraints Uanis(O1A) \\sim Ueq, Uanis(O1) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.002 4. Rigid body (RIGU) restrains S1, C2, C15, C14, C13, C1, C11, C16, O1, C12, C4, C3, C5 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001 S1A, C2A, C1A, C4A, C3A, O1A, C5A, C11A, C12A, C15A, C16A, C14A, C13A with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001 5. Others Fixed Sof: S1(0.7) S1A(0.3) O1(0.7) O1A(0.3) C1(0.7) C2(0.7) H2(0.7) C3(0.7) H3(0.7) C4(0.7) C5(0.7) H5(0.7) C11(0.7) C12(0.7) H12(0.7) C13(0.7) H13(0.7) C14(0.7) C15(0.7) H15(0.7) C16(0.7) H16(0.7) C1A(0.3) C2A(0.3) H2A(0.3) C3A(0.3) H3A(0.3) C4A(0.3) C5A(0.3) H5A(0.3) C11A(0.3) C12A(0.3) H12A(0.3) C13A(0.3) H13A(0.3) C14A(0.3) C15A(0.3) H15A(0.3) C16A(0.3) H16A(0.3) 6.a Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C5(H5), C12(H12), C13(H13), C15(H15), C16(H16), C2A(H2A), C3A(H3A), C5A(H5A), C12A(H12A), C13A(H13A), C15A(H15A), C16A(H16A), C22(H22), C23(H23), C25(H25), C26(H26), C32(H32), C33(H33), C35(H35), C36(H36) 6.b Idealised Me refined as rotating group: C20(H20A,H20B,H20C), C30(H30A,H30B,H30C) ; _olex2_date_sample_data_collection 2017-12-20 _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 1.122 _oxdiff_exptl_absorpt_empirical_full_min 0.884 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, 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 S1 S 0.2189(2) 0.52675(11) -0.1358(2) 0.0247(4) Uani 0.7 1 d D U P A 1 S1A S 0.1980(3) 0.46458(14) 0.0509(2) 0.0307(5) Uani 0.3 1 d D U P A 2 O1 O -0.01295(16) 0.46217(8) -0.36017(15) 0.0416(3) Uani 0.7 1 d . U P A 1 O1A O -0.1064(4) 0.3810(2) -0.2289(4) 0.0461(8) Uani 0.3 1 d . U P A 2 O2 O 0.93421(11) 0.91906(5) 0.09597(10) 0.0348(2) Uani 1 1 d . . . . . O3 O 0.88273(11) 0.68768(5) 0.83729(9) 0.0340(2) Uani 1 1 d . . . . . N1 N 0.74450(12) 0.69056(5) 0.30302(10) 0.0269(2) Uani 1 1 d . . . . . C1 C 0.2918(3) 0.51944(15) 0.0304(2) 0.0233(6) Uani 0.7 1 d D U P A 1 C2 C 0.2293(5) 0.4697(3) 0.0828(5) 0.0340(9) Uani 0.7 1 d . U P A 1 H2 H 0.2560 0.4586 0.1695 0.041 Uiso 0.7 1 calc R . P A 1 C3 C 0.1159(2) 0.43663(9) -0.0153(2) 0.0250(4) Uani 0.7 1 d . U P A 1 H3 H 0.0600 0.4020 0.0022 0.030 Uiso 0.7 1 calc R . P A 1 C4 C 0.0988(2) 0.46129(12) -0.1365(3) 0.0245(5) Uani 0.7 1 d D U P A 1 C5 C -0.0011(2) 0.43893(10) -0.2547(2) 0.0325(4) Uani 0.7 1 d . U P A 1 H5 H -0.0619 0.4035 -0.2498 0.039 Uiso 0.7 1 calc R . P A 1 C11 C 0.4079(5) 0.5634(3) 0.0988(3) 0.0209(7) Uani 0.7 1 d D U P A 1 C12 C 0.4897(7) 0.5992(4) 0.0355(6) 0.0229(10) Uani 0.7 1 d D U P A 1 H12 H 0.4666 0.5947 -0.0531 0.027 Uiso 0.7 1 calc R . P A 1 C13 C 0.6035(9) 0.6409(5) 0.0975(6) 0.0221(12) Uani 0.7 1 d D U P A 1 H13 H 0.6569 0.6627 0.0522 0.027 Uiso 0.7 1 calc R . P A 1 C14 C 0.6351(10) 0.6491(5) 0.2309(7) 0.0215(11) Uani 0.7 1 d D U P A 1 C15 C 0.5542(6) 0.6137(3) 0.2978(5) 0.0222(9) Uani 0.7 1 d D U P A 1 H15 H 0.5755 0.6190 0.3861 0.027 Uiso 0.7 1 calc R . P A 1 C16 C 0.4434(5) 0.5713(2) 0.2322(3) 0.0221(8) Uani 0.7 1 d D U P A 1 H16 H 0.3920 0.5478 0.2774 0.027 Uiso 0.7 1 calc R . P A 1 C1A C 0.2835(8) 0.5244(4) -0.0090(7) 0.0286(13) Uani 0.3 1 d D U P A 2 C2A C 0.217(2) 0.5257(11) -0.132(2) 0.026(3) Uani 0.3 1 d . U P A 2 H2A H 0.2424 0.5592 -0.1815 0.031 Uiso 0.3 1 calc R . P A 2 C3A C 0.1168(6) 0.4823(3) -0.1901(6) 0.0398(11) Uani 0.3 1 d . U P A 2 H3A H 0.0746 0.4780 -0.2781 0.048 Uiso 0.3 1 calc R . P A 2 C4A C 0.0865(7) 0.4449(4) -0.0979(8) 0.0342(12) Uani 0.3 1 d D U P A 2 C5A C -0.0300(6) 0.3957(3) -0.1224(5) 0.0423(10) Uani 0.3 1 d . U P A 2 H5A H -0.0467 0.3744 -0.0524 0.051 Uiso 0.3 1 calc R . P A 2 C11A C 0.4068(15) 0.5647(8) 0.0729(10) 0.0282(17) Uani 0.3 1 d D U P A 2 C12A C 0.4994(18) 0.6007(10) 0.0227(16) 0.029(2) Uani 0.3 1 d D U P A 2 H12A H 0.4934 0.5985 -0.0637 0.034 Uiso 0.3 1 calc R . P A 2 C13A C 0.601(2) 0.6402(13) 0.1093(17) 0.030(3) Uani 0.3 1 d D U P A 2 H13A H 0.6597 0.6657 0.0740 0.036 Uiso 0.3 1 calc R . P A 2 C14A C 0.628(3) 0.6470(14) 0.2400(19) 0.028(3) Uani 0.3 1 d D U P A 2 C15A C 0.5359(16) 0.6076(9) 0.2847(14) 0.031(2) Uani 0.3 1 d D U P A 2 H15A H 0.5453 0.6073 0.3719 0.037 Uiso 0.3 1 calc R . P A 2 C16A C 0.4308(12) 0.5692(6) 0.2022(10) 0.0282(18) Uani 0.3 1 d D U P A 2 H16A H 0.3715 0.5444 0.2374 0.034 Uiso 0.3 1 calc R . P A 2 C20 C 0.83220(18) 0.96591(7) 0.02091(16) 0.0386(3) Uani 1 1 d . . . . . H20A H 0.7725 0.9429 -0.0534 0.058 Uiso 1 1 calc GR . . . . H20B H 0.8802 1.0031 -0.0055 0.058 Uiso 1 1 calc GR . . . . H20C H 0.7753 0.9832 0.0711 0.058 Uiso 1 1 calc GR . . . . C21 C 0.78868(14) 0.74802(6) 0.24406(12) 0.0247(3) Uani 1 1 d . . . . . C22 C 0.69160(14) 0.79041(6) 0.15938(13) 0.0267(3) Uani 1 1 d . . . . . H22 H 0.5954 0.7802 0.1373 0.032 Uiso 1 1 calc R . . . . C23 C 0.73597(14) 0.84767(7) 0.10730(13) 0.0276(3) Uani 1 1 d . . . . . H23 H 0.6699 0.8753 0.0500 0.033 Uiso 1 1 calc R . . . . C24 C 0.87989(14) 0.86366(7) 0.14114(13) 0.0278(3) Uani 1 1 d . . . . . C25 C 0.97796(14) 0.82152(7) 0.22631(13) 0.0287(3) Uani 1 1 d . . . . . H25 H 1.0741 0.8320 0.2493 0.034 Uiso 1 1 calc R . . . . C26 C 0.93265(14) 0.76405(7) 0.27681(12) 0.0278(3) Uani 1 1 d . . . . . H26 H 0.9988 0.7360 0.3330 0.033 Uiso 1 1 calc R . . . . C30 C 0.85926(16) 0.74596(7) 0.90647(13) 0.0337(3) Uani 1 1 d . . . . . H30A H 0.7610 0.7586 0.8761 0.051 Uiso 1 1 calc GR . . . . H30B H 0.9165 0.7833 0.8936 0.051 Uiso 1 1 calc GR . . . . H30C H 0.8845 0.7352 0.9962 0.051 Uiso 1 1 calc GR . . . . C31 C 0.78190(13) 0.69185(7) 0.44052(12) 0.0254(3) Uani 1 1 d . . . . . C32 C 0.76038(14) 0.75021(7) 0.50399(13) 0.0276(3) Uani 1 1 d . . . . . H32 H 0.7229 0.7891 0.4571 0.033 Uiso 1 1 calc R . . . . C33 C 0.79417(14) 0.75132(7) 0.63699(13) 0.0276(3) Uani 1 1 d . . . . . H33 H 0.7812 0.7910 0.6789 0.033 Uiso 1 1 calc R . . . . C34 C 0.84741(13) 0.69282(7) 0.70673(13) 0.0267(3) Uani 1 1 d . . . . . C35 C 0.86985(14) 0.63393(7) 0.64342(13) 0.0273(3) Uani 1 1 d . . . . . H35 H 0.9057 0.5948 0.6901 0.033 Uiso 1 1 calc R . . . . C36 C 0.83882(14) 0.63380(7) 0.51158(13) 0.0266(3) Uani 1 1 d . . . . . H36 H 0.8559 0.5948 0.4699 0.032 Uiso 1 1 calc R . . . . 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 S1 0.0251(6) 0.0217(6) 0.0234(3) 0.0007(3) 0.0013(3) -0.0022(6) S1A 0.0328(11) 0.0298(8) 0.0312(10) 0.0031(7) 0.0123(8) -0.0001(7) O1 0.0356(7) 0.0438(8) 0.0385(7) -0.0100(6) 0.0009(6) 0.0042(6) O1A 0.0430(14) 0.0432(15) 0.0482(13) -0.0028(11) 0.0077(11) -0.0009(12) O2 0.0376(5) 0.0232(5) 0.0486(6) 0.0030(4) 0.0205(5) -0.0049(4) O3 0.0449(6) 0.0312(5) 0.0274(5) -0.0003(4) 0.0132(4) 0.0018(4) N1 0.0314(6) 0.0227(5) 0.0277(6) 0.0000(4) 0.0104(5) -0.0041(4) C1 0.0230(9) 0.0204(10) 0.0249(10) -0.0009(8) 0.0047(8) 0.0038(7) C2 0.0324(17) 0.0320(13) 0.0350(15) -0.0014(11) 0.0062(11) -0.0049(11) C3 0.0214(9) 0.0214(8) 0.0302(9) -0.0031(7) 0.0049(7) -0.0034(7) C4 0.0222(9) 0.0201(11) 0.0307(10) -0.0015(8) 0.0071(8) -0.0018(7) C5 0.0248(9) 0.0277(9) 0.0398(8) -0.0103(7) 0.0018(7) 0.0019(7) C11 0.0219(10) 0.0182(12) 0.0230(14) 0.0013(10) 0.0074(10) 0.0030(8) C12 0.0250(14) 0.0193(16) 0.0246(14) -0.0007(10) 0.0078(10) 0.0011(12) C13 0.0246(16) 0.0169(19) 0.0263(15) 0.0013(11) 0.0096(11) 0.0007(15) C14 0.0220(17) 0.017(2) 0.0278(16) 0.0011(11) 0.0104(10) 0.0005(15) C15 0.0225(15) 0.0192(16) 0.0248(13) -0.0007(9) 0.0072(10) -0.0016(12) C16 0.0243(13) 0.0217(13) 0.0210(13) 0.0012(10) 0.0080(10) -0.0018(10) C1A 0.030(2) 0.023(2) 0.036(2) 0.0028(16) 0.0145(16) 0.0034(16) C2A 0.025(4) 0.023(5) 0.034(2) 0.0006(18) 0.0147(18) 0.013(4) C3A 0.040(2) 0.039(2) 0.0406(18) 0.0002(15) 0.0111(15) -0.0002(17) C4A 0.0334(18) 0.031(2) 0.0379(18) -0.0006(15) 0.0107(15) 0.0036(16) C5A 0.0388(18) 0.039(2) 0.0468(17) 0.0003(14) 0.0095(13) -0.0025(16) C11A 0.031(2) 0.022(3) 0.034(3) 0.005(2) 0.0147(19) 0.003(2) C12A 0.030(3) 0.022(4) 0.037(3) 0.006(2) 0.016(2) 0.002(3) C13A 0.031(4) 0.025(5) 0.038(3) 0.004(2) 0.017(2) 0.000(4) C14A 0.028(4) 0.022(5) 0.037(3) 0.004(2) 0.015(2) 0.003(4) C15A 0.032(4) 0.028(4) 0.036(3) 0.003(2) 0.016(2) -0.003(3) C16A 0.030(3) 0.023(3) 0.036(3) 0.004(2) 0.015(2) -0.001(2) C20 0.0482(9) 0.0250(7) 0.0487(9) 0.0048(6) 0.0235(7) -0.0027(6) C21 0.0289(6) 0.0208(6) 0.0271(6) -0.0026(5) 0.0125(5) -0.0026(5) C22 0.0252(6) 0.0230(6) 0.0344(7) -0.0018(5) 0.0130(5) -0.0011(5) C23 0.0293(7) 0.0220(6) 0.0336(7) 0.0007(5) 0.0127(5) 0.0021(5) C24 0.0336(7) 0.0207(6) 0.0344(7) -0.0048(5) 0.0179(6) -0.0040(5) C25 0.0253(6) 0.0280(7) 0.0346(7) -0.0049(5) 0.0120(5) -0.0048(5) C26 0.0282(7) 0.0257(6) 0.0299(6) -0.0018(5) 0.0093(5) 0.0008(5) C30 0.0409(8) 0.0324(7) 0.0307(7) -0.0055(5) 0.0150(6) -0.0058(6) C31 0.0257(6) 0.0244(6) 0.0279(6) 0.0002(5) 0.0108(5) -0.0029(5) C32 0.0284(6) 0.0223(6) 0.0338(7) 0.0032(5) 0.0120(5) 0.0015(5) C33 0.0299(7) 0.0229(6) 0.0337(7) -0.0036(5) 0.0150(5) -0.0005(5) C34 0.0256(6) 0.0277(7) 0.0289(6) -0.0006(5) 0.0113(5) -0.0030(5) C35 0.0267(6) 0.0229(6) 0.0324(7) 0.0027(5) 0.0092(5) 0.0000(5) C36 0.0269(6) 0.0219(6) 0.0328(7) -0.0024(5) 0.0117(5) -0.0007(5) 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' S S 0.3331 0.5567 '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 C4 S1 C1 90.60(18) C1A S1A C4A 92.4(4) C24 O2 C20 115.56(11) C34 O3 C30 117.64(11) C14 N1 C21 119.6(3) C14 N1 C31 121.0(2) C14A N1 C21 124.2(8) C14A N1 C31 115.5(6) C21 N1 C31 116.19(10) C2 C1 S1 113.5(2) C2 C1 C11 126.4(3) C11 C1 S1 120.1(2) C1 C2 C3 110.7(3) C4 C3 C2 113.6(3) C3 C4 S1 111.67(17) C3 C4 C5 127.7(2) C5 C4 S1 120.6(2) O1 C5 C4 125.7(2) C12 C11 C1 121.8(3) C12 C11 C16 117.3(3) C16 C11 C1 120.8(3) C13 C12 C11 123.8(6) C12 C13 C14 117.8(8) N1 C14 C13 123.1(4) N1 C14 C15 117.1(5) C13 C14 C15 119.8(7) C16 C15 C14 120.4(5) C15 C16 C11 120.9(3) C2A C1A S1A 105.0(12) C2A C1A C11A 132.0(13) C11A C1A S1A 123.0(6) C1A C2A C3A 124(2) C2A C3A C4A 107.2(13) C3A C4A S1A 111.3(5) C3A C4A C5A 124.1(6) C5A C4A S1A 124.6(6) O1A C5A C4A 123.9(6) C12A C11A C1A 122.9(8) C16A C11A C1A 120.6(8) C16A C11A C12A 116.5(10) C13A C12A C11A 116.1(15) C14A C13A C12A 129(2) C13A C14A N1 115.7(12) C13A C14A C15A 112(2) C15A C14A N1 132.7(15) C16A C15A C14A 121.2(15) C11A C16A C15A 125.2(10) C22 C21 N1 121.80(11) C22 C21 C26 118.87(12) C26 C21 N1 119.26(12) C23 C22 C21 121.05(12) C22 C23 C24 119.79(13) O2 C24 C23 124.30(13) O2 C24 C25 116.17(12) C23 C24 C25 119.54(12) C26 C25 C24 120.22(12) C25 C26 C21 120.53(12) C32 C31 N1 120.60(11) C32 C31 C36 119.29(12) C36 C31 N1 120.10(11) C31 C32 C33 120.79(12) C34 C33 C32 119.54(12) O3 C34 C33 124.70(12) O3 C34 C35 115.35(12) C33 C34 C35 119.94(12) C36 C35 C34 120.06(12) C35 C36 C31 120.34(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C1 1.747(3) S1 C4 1.746(3) S1A C1A 1.690(7) S1A C4A 1.712(7) O1 C5 1.213(3) O1A C5A 1.216(7) O2 C20 1.4259(19) O2 C24 1.3676(16) O3 C30 1.4266(17) O3 C34 1.3677(16) N1 C14 1.392(9) N1 C14A 1.43(2) N1 C21 1.4297(17) N1 C31 1.4366(17) C1 C2 1.369(6) C1 C11 1.449(4) C2 C3 1.450(4) C3 C4 1.373(4) C4 C5 1.438(3) C11 C12 1.402(4) C11 C16 1.403(3) C12 C13 1.390(6) C13 C14 1.406(5) C14 C15 1.417(5) C15 C16 1.391(4) C1A C2A 1.31(2) C1A C11A 1.501(13) C2A C3A 1.32(2) C3A C4A 1.351(9) C4A C5A 1.464(9) C11A C12A 1.394(10) C11A C16A 1.365(9) C12A C13A 1.392(14) C13A C14A 1.379(13) C14A C15A 1.394(13) C15A C16A 1.376(10) C21 C22 1.3898(19) C21 C26 1.3952(19) C22 C23 1.3876(18) C23 C24 1.3940(19) C24 C25 1.394(2) C25 C26 1.3864(19) C31 C32 1.3867(18) C31 C36 1.3961(19) C32 C33 1.3911(19) C33 C34 1.3888(19) C34 C35 1.3971(19) C35 C36 1.3810(19) 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 S1 C1 C2 C3 -0.9(5) S1 C1 C11 C12 -17.2(6) S1 C1 C11 C16 163.2(3) S1 C4 C5 O1 -0.7(3) S1A C1A C2A C3A -6.7(18) S1A C1A C11A C12A 163.2(11) S1A C1A C11A C16A -18.8(15) S1A C4A C5A O1A -178.2(5) O2 C24 C25 C26 -179.83(11) O3 C34 C35 C36 -179.46(11) N1 C14 C15 C16 -179.9(6) N1 C14A C15A C16A -180(2) N1 C21 C22 C23 177.18(11) N1 C21 C26 C25 -176.61(11) N1 C31 C32 C33 178.88(11) N1 C31 C36 C35 -177.49(11) C1 S1 C4 C3 0.2(2) C1 S1 C4 C5 -179.2(2) C1 C2 C3 C4 1.1(5) C1 C11 C12 C13 -178.9(9) C1 C11 C16 C15 -179.6(4) C2 C1 C11 C12 162.2(5) C2 C1 C11 C16 -17.4(6) C2 C3 C4 S1 -0.8(3) C2 C3 C4 C5 178.6(3) C3 C4 C5 O1 179.9(2) C4 S1 C1 C2 0.4(4) C4 S1 C1 C11 179.9(3) C11 C1 C2 C3 179.6(4) C11 C12 C13 C14 -2.0(13) C12 C11 C16 C15 0.8(6) C12 C13 C14 N1 -178.7(10) C12 C13 C14 C15 1.8(12) C13 C14 C15 C16 -0.3(11) C14 N1 C21 C22 41.6(5) C14 N1 C21 C26 -141.5(5) C14 N1 C31 C32 -113.3(6) C14 N1 C31 C36 65.9(6) C14 C15 C16 C11 -1.0(8) C16 C11 C12 C13 0.7(10) C1A S1A C4A C3A 1.3(6) C1A S1A C4A C5A -176.7(6) C1A C2A C3A C4A 7.7(19) C1A C11A C12A C13A 175(2) C1A C11A C16A C15A -176.3(12) C2A C1A C11A C12A -18(2) C2A C1A C11A C16A 160.1(14) C2A C3A C4A S1A -4.6(11) C2A C3A C4A C5A 173.4(9) C3A C4A C5A O1A 4.0(10) C4A S1A C1A C2A 2.5(10) C4A S1A C1A C11A -178.2(9) C11A C1A C2A C3A 174.2(12) C11A C12A C13A C14A 3(4) C12A C11A C16A C15A 1.8(18) C12A C13A C14A N1 178(3) C12A C13A C14A C15A 0(4) C13A C14A C15A C16A -1(3) C14A N1 C21 C22 37.9(13) C14A N1 C21 C26 -145.2(13) C14A N1 C31 C32 -112.0(13) C14A N1 C31 C36 67.2(13) C14A C15A C16A C11A 1(2) C16A C11A C12A C13A -3(2) C20 O2 C24 C23 7.01(18) C20 O2 C24 C25 -173.05(12) C21 N1 C14 C13 27.5(11) C21 N1 C14 C15 -153.0(6) C21 N1 C14A C13A 30(3) C21 N1 C14A C15A -152(2) C21 N1 C31 C32 46.34(16) C21 N1 C31 C36 -134.48(12) C21 C22 C23 C24 -0.73(19) C22 C21 C26 C25 0.38(19) C22 C23 C24 O2 -179.53(12) C22 C23 C24 C25 0.54(19) C23 C24 C25 C26 0.10(19) C24 C25 C26 C21 -0.57(19) C26 C21 C22 C23 0.27(19) C30 O3 C34 C33 1.95(19) C30 O3 C34 C35 -178.79(12) C31 N1 C14 C13 -173.6(7) C31 N1 C14 C15 6.0(10) C31 N1 C14A C13A -173.6(16) C31 N1 C14A C15A 5(3) C31 N1 C21 C22 -118.36(13) C31 N1 C21 C26 58.55(16) C31 C32 C33 C34 -1.31(19) C32 C31 C36 C35 1.70(19) C32 C33 C34 O3 -179.23(12) C32 C33 C34 C35 1.54(19) C33 C34 C35 C36 -0.16(19) C34 C35 C36 C31 -1.47(19) C36 C31 C32 C33 -0.30(19)