#------------------------------------------------------------------------------ #$Date: 2019-11-17 09:21:32 +0200 (Sun, 17 Nov 2019) $ #$Revision: 229073 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229950.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_7229950 loop_ _publ_author_name 'Chen, Xin' 'Li, Duanxiu' 'Luo, Chun' 'Wang, Jinqiu' 'Deng, Zongwu' 'Zhang, Hailu' _publ_section_title ; Cocrystals of zileuton with enhanced physical stability ; _journal_issue 7 _journal_name_full CrystEngComm _journal_page_first 990 _journal_paper_doi 10.1039/C7CE02150J _journal_volume 20 _journal_year 2018 _chemical_formula_moiety 'C11 H12 N2 O2 S' _chemical_formula_sum 'C11 H12 N2 O2 S' _chemical_formula_weight 236.29 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2017-12-05 deposited with the CCDC. 2018-01-11 downloaded from the CCDC. ; _cell_angle_alpha 87.300(14) _cell_angle_beta 87.390(13) _cell_angle_gamma 81.545(14) _cell_formula_units_Z 4 _cell_length_a 5.224(3) _cell_length_b 6.014(4) _cell_length_c 36.61(2) _cell_measurement_reflns_used 5229 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 26.489 _cell_measurement_theta_min 2.229 _cell_volume 1135.5(12) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_reduction 'SAINT v8.37A (Bruker, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0742 _diffrn_reflns_av_unetI/netI 0.0826 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_number 4307 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.679 _diffrn_reflns_theta_min 2.787 _exptl_absorpt_coefficient_mu 0.271 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.5484 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS 2014/5' _exptl_crystal_colour 'clear colourless' _exptl_crystal_density_diffrn 1.382 _exptl_crystal_description needle _exptl_crystal_F_000 496.15 _refine_diff_density_max 0.283 _refine_diff_density_min -0.544 _refine_diff_density_rms 0.074 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 292 _refine_ls_number_reflns 4307 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.067 _refine_ls_R_factor_all 0.0939 _refine_ls_R_factor_gt 0.0654 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0360P)^2^+1.8158P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1331 _refine_ls_wR_factor_ref 0.1426 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3280 _reflns_number_total 4307 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ce02150j2.cif _cod_data_source_block FA _cod_depositor_comments 'Adding full bibliography for 7229950--7229953.cif.' _cod_database_code 7229950 _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. ; _shelx_res_file ; FA.res created by SHELXL-2014/7 TITL 20161217ziP -19_0m R = 0.11 CELL 0.71073 5.224 6.014 36.61 87.3 87.39 81.545 ZERR 4 0.003 0.004 0.02 0.014 0.013 0.014 LATT 1 SFAC C 2.310 20.844 1.02 10.208 1.589 0.569 0.865 51.651 0.216 0.003 0.002 = 11.5 0.68 12.01 SFAC H 0.493 10.511 0.323 26.126 0.14 3.142 0.041 57.8 0.003 0 0 0.624 0.35 = 1.008 SFAC N 12.213 0.006 3.132 9.893 2.013 28.998 1.166 0.583 -11.529 0.006 = 0.003 19.6 0.68 14.01 SFAC O 3.049 13.277 2.287 5.701 1.546 0.324 0.867 32.909 0.251 0.011 0.006 = 32.5 0.68 16 SFAC S 6.905 1.468 5.203 22.215 1.438 0.254 1.586 56.172 0.867 0.125 0.123 = 532 1.04 32.06 UNIT 44 48 8 8 4 L.S. 5 PLAN -20 TEMP 23 HTAB O1 O2_$1 HTAB N2 O2_$2 HTAB N2 O1_$3 HTAB O3 O4_$4 HTAB N4 O4_$5 HTAB N4 O3_$6 EQIV $1 -1+x,y,z EQIV $2 2-x,2-y,1-z EQIV $3 1-x,1-y,1-z EQIV $4 1+x,y,z EQIV $5 -1-x,1-y,2-z EQIV $6 -x,2-y,2-z BOND $H CONF MORE -1 fmap 2 acta SHEL 999 0.82 REM REM REM WGHT 0.035980 1.815846 BASF 0.15178 FVAR 10.46316 S1 5 0.381204 0.949833 0.372421 11.00000 0.02314 0.02298 = 0.02965 -0.00238 -0.00075 0.00118 O1 4 0.476324 0.609720 0.456765 11.00000 0.01543 0.03228 = 0.02932 0.00428 0.00077 -0.01100 AFIX 3 H1 2 0.330414 0.679110 0.454265 11.00000 -1.50000 AFIX 0 O2 4 1.017963 0.889778 0.456248 11.00000 0.01450 0.03071 = 0.03154 -0.00249 0.00197 -0.00938 N1 3 0.662548 0.741347 0.441653 11.00000 0.01323 0.02638 = 0.02146 -0.00098 -0.00051 -0.01053 N2 3 0.750795 0.785999 0.502324 11.00000 0.02076 0.03579 = 0.02462 -0.00179 -0.00200 -0.01279 AFIX 3 H2A 2 0.842985 0.830399 0.518694 11.00000 -1.20000 H2B 2 0.614085 0.727599 0.508794 11.00000 -1.20000 AFIX 0 C8 1 0.576221 0.688330 0.378119 11.00000 0.01806 0.01761 = 0.02222 0.00333 0.00336 -0.00100 C9 1 0.778877 0.658592 0.406479 11.00000 0.01932 0.02599 = 0.02402 -0.00317 0.00288 -0.00327 AFIX 13 H9 2 0.909884 0.753549 0.398525 11.00000 -1.20000 AFIX 0 C11 1 0.820496 0.806527 0.467047 11.00000 0.01222 0.01876 = 0.02556 0.00033 -0.00032 0.00286 C10 1 0.916531 0.415679 0.410030 11.00000 0.03033 0.03007 = 0.03624 -0.00518 -0.00447 0.00983 AFIX 137 H10A 2 1.049781 0.406390 0.427482 11.00000 -1.50000 H10B 2 0.992506 0.370283 0.386687 11.00000 -1.50000 H10C 2 0.793513 0.318239 0.418144 11.00000 -1.50000 AFIX 0 C7 1 0.525802 0.538120 0.353490 11.00000 0.02489 0.02381 = 0.02362 -0.00054 -0.00089 -0.00292 AFIX 43 H7 2 0.613261 0.392155 0.352340 11.00000 -1.20000 AFIX 0 C6 1 0.320818 0.631259 0.329317 11.00000 0.02362 0.02778 = 0.02397 0.00034 0.00305 -0.00797 C1 1 0.223090 0.854845 0.336666 11.00000 0.02020 0.03242 = 0.02552 0.00086 0.00590 -0.00416 C2 1 0.015616 0.974599 0.317311 11.00000 0.02234 0.03726 = 0.03060 0.00959 0.00053 0.00233 AFIX 43 H2 2 -0.048130 1.123070 0.322363 11.00000 -1.20000 AFIX 0 C3 1 -0.090185 0.865600 0.290691 11.00000 0.02101 0.06098 = 0.03090 0.01215 -0.00678 -0.00691 AFIX 43 H3 2 -0.228828 0.940953 0.277863 11.00000 -1.20000 AFIX 0 C4 1 0.007982 0.643180 0.282684 11.00000 0.03634 0.05970 = 0.02344 -0.00263 -0.00199 -0.01697 AFIX 43 H4 2 -0.065085 0.573400 0.264435 11.00000 -1.20000 AFIX 0 C5 1 0.213289 0.525186 0.301652 11.00000 0.03972 0.03831 = 0.02444 -0.00470 -0.00103 -0.01175 AFIX 43 H5 2 0.278431 0.377848 0.296063 11.00000 -1.20000 AFIX 0 S2 5 0.186093 0.653447 0.869038 11.00000 0.02271 0.02393 = 0.03021 -0.00156 0.00052 -0.00166 O3 4 0.045587 0.913926 0.956461 11.00000 0.01329 0.03393 = 0.02773 -0.00358 -0.00251 -0.01017 AFIX 3 H3A 2 0.193797 0.849326 0.953141 11.00000 -1.50000 AFIX 0 O4 4 -0.495723 0.632452 0.955639 11.00000 0.01620 0.02967 = 0.02778 0.00038 -0.00294 -0.01077 N3 3 -0.132495 0.790295 0.940942 11.00000 0.01360 0.02408 = 0.02302 -0.00448 -0.00445 -0.00871 N4 3 -0.248870 0.709066 1.001633 11.00000 0.02232 0.03254 = 0.02396 0.00040 0.00001 -0.01111 AFIX 3 H4A 2 -0.345460 0.651766 1.018033 11.00000 -1.20000 H4B 2 -0.116370 0.765876 1.007933 11.00000 -1.20000 AFIX 0 C19 1 -0.023501 0.902352 0.877875 11.00000 0.01638 0.01942 = 0.02370 -0.00629 -0.00585 -0.00240 C20 1 -0.238179 0.900233 0.906769 11.00000 0.01710 0.02443 = 0.02415 -0.00191 -0.00352 -0.00604 AFIX 13 H20 2 -0.360749 0.807651 0.898112 11.00000 -1.20000 AFIX 0 C22 1 -0.304347 0.710868 0.966511 11.00000 0.01524 0.01534 = 0.02325 0.00057 -0.00220 -0.00010 C21 1 -0.386585 1.135115 0.912406 11.00000 0.02637 0.03159 = 0.03970 -0.00063 0.00718 0.00566 AFIX 137 H21A 2 -0.526298 1.125837 0.930115 11.00000 -1.50000 H21B 2 -0.455009 1.197037 0.889612 11.00000 -1.50000 H21C 2 -0.271785 1.230195 0.921037 11.00000 -1.50000 AFIX 0 C18 1 0.027519 1.075619 0.855215 11.00000 0.02268 0.02195 = 0.02586 -0.00222 -0.00255 -0.00548 AFIX 43 H18 2 -0.066780 1.219186 0.855988 11.00000 -1.20000 AFIX 0 C17 1 0.242631 1.016073 0.829702 11.00000 0.02463 0.03234 = 0.02326 -0.00292 -0.00286 -0.01141 C12 1 0.349739 0.788792 0.834314 11.00000 0.02126 0.03037 = 0.02421 -0.00713 -0.00395 -0.00487 C13 1 0.567142 0.697948 0.812919 11.00000 0.02585 0.04258 = 0.03451 -0.01166 0.00222 -0.00720 AFIX 43 H13 2 0.638389 0.547470 0.815921 11.00000 -1.20000 AFIX 0 C14 1 0.672053 0.839110 0.787247 11.00000 0.02465 0.07124 = 0.02657 -0.01513 0.00854 -0.01587 AFIX 43 H14 2 0.816181 0.782002 0.772920 11.00000 -1.20000 AFIX 0 C15 1 0.566819 1.064288 0.782400 11.00000 0.03496 0.07074 = 0.02333 0.00035 0.00059 -0.02110 AFIX 43 H15 2 0.640780 1.155051 0.764885 11.00000 -1.20000 AFIX 0 C16 1 0.354118 1.154059 0.803299 11.00000 0.03661 0.04022 = 0.02902 0.00208 -0.00332 -0.01117 AFIX 43 H16 2 0.284743 1.304791 0.799976 11.00000 -1.20000 AFIX 0 HKLF 5 REM 20161217ziP -19_0m R = 0.11 REM R1 = 0.0654 for 3280 Fo > 4sig(Fo) and 0.0939 for all 4307 data REM 292 parameters refined using 0 restraints END WGHT 0.0405 1.5056 REM Highest difference peak 0.283, deepest hole -0.544, 1-sigma level 0.074 Q1 1 0.8038 0.8958 0.5203 11.00000 0.05 0.28 Q2 1 0.4636 0.3315 0.3713 11.00000 0.05 0.28 Q3 1 -0.0728 1.3225 0.8635 11.00000 0.05 0.28 Q4 1 0.5000 0.5000 0.5000 10.50000 0.05 0.27 Q5 1 0.0783 1.1347 0.2890 11.00000 0.05 0.26 Q6 1 -0.0953 1.2791 0.3433 11.00000 0.05 0.25 Q7 1 0.8812 0.5501 0.3608 11.00000 0.05 0.24 Q8 1 0.4479 0.5881 0.3406 11.00000 0.05 0.24 Q9 1 0.2876 0.8887 0.3492 11.00000 0.05 0.24 Q10 1 0.3927 0.4656 0.8997 11.00000 0.05 0.24 Q11 1 0.1002 0.6276 0.3683 11.00000 0.05 0.24 Q12 1 0.5355 0.2334 0.4032 11.00000 0.05 0.23 Q13 1 0.9619 0.8246 0.4292 11.00000 0.05 0.23 Q14 1 -0.5193 1.0318 0.9507 11.00000 0.05 0.23 Q15 1 0.0872 0.3392 0.3299 11.00000 0.05 0.23 Q16 1 0.0376 0.7930 0.8686 11.00000 0.05 0.23 Q17 1 0.6092 1.0076 0.3238 11.00000 0.05 0.23 Q18 1 0.3752 1.0105 0.3413 11.00000 0.05 0.23 Q19 1 0.6263 0.1967 0.2498 11.00000 0.05 0.22 Q20 1 0.6595 0.6664 0.3913 11.00000 0.05 0.22 ; _shelx_res_checksum 97278 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 S1 S 0.38120(19) 0.94983(17) 0.37242(3) 0.0257(3) Uani 1 1 d . . O1 O 0.4763(5) 0.6097(5) 0.45676(7) 0.0251(6) Uani 1 1 d . . H1 H 0.3304 0.6791 0.4543 0.038 Uiso 1 1 d R U O2 O 1.0180(5) 0.8898(5) 0.45625(7) 0.0250(6) Uani 1 1 d . . N1 N 0.6625(5) 0.7413(5) 0.44165(8) 0.0196(7) Uani 1 1 d . . N2 N 0.7508(6) 0.7860(6) 0.50232(9) 0.0261(8) Uani 1 1 d . . H2A H 0.8430 0.8304 0.5187 0.031 Uiso 1 1 d R U H2B H 0.6141 0.7276 0.5088 0.031 Uiso 1 1 d R U C8 C 0.5762(7) 0.6883(6) 0.37812(10) 0.0197(8) Uani 1 1 d . . C9 C 0.7789(7) 0.6586(7) 0.40648(10) 0.0232(9) Uani 1 1 d . . H9 H 0.9099 0.7535 0.3985 0.028 Uiso 1 1 calc R U C11 C 0.8205(7) 0.8065(6) 0.46705(10) 0.0194(8) Uani 1 1 d . . C10 C 0.9165(8) 0.4157(7) 0.41003(12) 0.0334(11) Uani 1 1 d . . H10A H 1.0498 0.4064 0.4275 0.050 Uiso 1 1 calc R U H10B H 0.9925 0.3703 0.3867 0.050 Uiso 1 1 calc R U H10C H 0.7935 0.3182 0.4181 0.050 Uiso 1 1 calc R U C7 C 0.5258(7) 0.5381(7) 0.35349(10) 0.0242(9) Uani 1 1 d . . H7 H 0.6133 0.3922 0.3523 0.029 Uiso 1 1 calc R U C6 C 0.3208(7) 0.6313(7) 0.32932(11) 0.0249(9) Uani 1 1 d . . C1 C 0.2231(7) 0.8548(7) 0.33667(11) 0.0263(9) Uani 1 1 d . . C2 C 0.0156(8) 0.9746(8) 0.31731(11) 0.0311(10) Uani 1 1 d . . H2 H -0.0481 1.1231 0.3224 0.037 Uiso 1 1 calc R U C3 C -0.0902(8) 0.8656(9) 0.29069(12) 0.0378(12) Uani 1 1 d . . H3 H -0.2288 0.9410 0.2779 0.045 Uiso 1 1 calc R U C4 C 0.0080(9) 0.6432(9) 0.28268(12) 0.0388(12) Uani 1 1 d . . H4 H -0.0651 0.5734 0.2644 0.047 Uiso 1 1 calc R U C5 C 0.2133(8) 0.5252(8) 0.30165(11) 0.0334(10) Uani 1 1 d . . H5 H 0.2784 0.3778 0.2961 0.040 Uiso 1 1 calc R U S2 S 0.18609(19) 0.65345(18) 0.86904(3) 0.0258(3) Uani 1 1 d . . O3 O 0.0456(5) 0.9139(5) 0.95646(7) 0.0242(6) Uani 1 1 d . . H3A H 0.1938 0.8493 0.9531 0.036 Uiso 1 1 d R U O4 O -0.4957(5) 0.6325(4) 0.95564(7) 0.0238(6) Uani 1 1 d . . N3 N -0.1325(5) 0.7903(5) 0.94094(8) 0.0194(7) Uani 1 1 d . . N4 N -0.2489(6) 0.7091(6) 1.00163(9) 0.0256(8) Uani 1 1 d . . H4A H -0.3455 0.6518 1.0180 0.031 Uiso 1 1 d R U H4B H -0.1164 0.7659 1.0079 0.031 Uiso 1 1 d R U C19 C -0.0235(7) 0.9024(6) 0.87788(10) 0.0195(8) Uani 1 1 d . . C20 C -0.2382(7) 0.9002(6) 0.90677(10) 0.0215(9) Uani 1 1 d . . H20 H -0.3607 0.8077 0.8981 0.026 Uiso 1 1 calc R U C22 C -0.3043(7) 0.7109(6) 0.96651(10) 0.0182(8) Uani 1 1 d . . C21 C -0.3866(8) 1.1351(7) 0.91241(12) 0.0338(11) Uani 1 1 d . . H21A H -0.5263 1.1258 0.9301 0.051 Uiso 1 1 calc R U H21B H -0.4550 1.1970 0.8896 0.051 Uiso 1 1 calc R U H21C H -0.2718 1.2302 0.9210 0.051 Uiso 1 1 calc R U C18 C 0.0275(7) 1.0756(7) 0.85521(10) 0.0232(9) Uani 1 1 d . . H18 H -0.0668 1.2192 0.8560 0.028 Uiso 1 1 calc R U C17 C 0.2426(7) 1.0161(7) 0.82970(11) 0.0259(9) Uani 1 1 d . . C12 C 0.3497(7) 0.7888(7) 0.83431(11) 0.0249(9) Uani 1 1 d . . C13 C 0.5671(8) 0.6979(8) 0.81292(12) 0.0339(11) Uani 1 1 d . . H13 H 0.6384 0.5475 0.8159 0.041 Uiso 1 1 calc R U C14 C 0.6721(8) 0.8391(9) 0.78725(12) 0.0398(12) Uani 1 1 d . . H14 H 0.8162 0.7820 0.7729 0.048 Uiso 1 1 calc R U C15 C 0.5668(9) 1.0643(9) 0.78240(12) 0.0418(13) Uani 1 1 d . . H15 H 0.6408 1.1551 0.7649 0.050 Uiso 1 1 calc R U C16 C 0.3541(8) 1.1541(8) 0.80330(12) 0.0348(11) Uani 1 1 d . . H16 H 0.2847 1.3048 0.8000 0.042 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 S1 0.0231(5) 0.0230(6) 0.0296(6) -0.0024(4) -0.0007(4) 0.0012(4) O1 0.0154(13) 0.0323(17) 0.0293(16) 0.0043(13) 0.0008(12) -0.0110(12) O2 0.0145(13) 0.0307(17) 0.0315(16) -0.0025(12) 0.0020(11) -0.0094(12) N1 0.0132(15) 0.0264(19) 0.0215(18) -0.0010(14) -0.0005(13) -0.0105(14) N2 0.0208(17) 0.036(2) 0.0246(19) -0.0018(16) -0.0020(15) -0.0128(16) C8 0.0181(18) 0.018(2) 0.022(2) 0.0033(16) 0.0034(16) -0.0010(16) C9 0.0193(19) 0.026(2) 0.024(2) -0.0032(17) 0.0029(16) -0.0033(17) C11 0.0122(17) 0.019(2) 0.026(2) 0.0003(16) -0.0003(16) 0.0029(16) C10 0.030(2) 0.030(3) 0.036(3) -0.005(2) -0.004(2) 0.010(2) C7 0.025(2) 0.024(2) 0.024(2) -0.0005(17) -0.0009(17) -0.0029(17) C6 0.024(2) 0.028(2) 0.024(2) 0.0003(17) 0.0030(17) -0.0080(18) C1 0.020(2) 0.032(2) 0.026(2) 0.0009(18) 0.0059(17) -0.0042(18) C2 0.022(2) 0.037(3) 0.031(2) 0.010(2) 0.0005(18) 0.0023(19) C3 0.021(2) 0.061(3) 0.031(3) 0.012(2) -0.0068(19) -0.007(2) C4 0.036(3) 0.060(3) 0.023(2) -0.003(2) -0.002(2) -0.017(2) C5 0.040(3) 0.038(3) 0.024(2) -0.0047(19) -0.001(2) -0.012(2) S2 0.0227(5) 0.0239(6) 0.0302(6) -0.0016(4) 0.0005(4) -0.0017(4) O3 0.0133(12) 0.0339(17) 0.0277(15) -0.0036(12) -0.0025(11) -0.0102(12) O4 0.0162(13) 0.0297(16) 0.0278(15) 0.0004(12) -0.0029(11) -0.0108(12) N3 0.0136(15) 0.0241(18) 0.0230(18) -0.0045(14) -0.0045(13) -0.0087(14) N4 0.0223(17) 0.033(2) 0.0240(19) 0.0004(15) 0.0000(14) -0.0111(16) C19 0.0164(18) 0.019(2) 0.024(2) -0.0063(16) -0.0059(16) -0.0024(16) C20 0.0171(18) 0.024(2) 0.024(2) -0.0019(17) -0.0035(16) -0.0060(17) C22 0.0152(18) 0.015(2) 0.023(2) 0.0006(16) -0.0022(16) -0.0001(16) C21 0.026(2) 0.032(3) 0.040(3) -0.001(2) 0.0072(19) 0.0057(19) C18 0.023(2) 0.022(2) 0.026(2) -0.0022(17) -0.0026(17) -0.0055(17) C17 0.025(2) 0.032(2) 0.023(2) -0.0029(18) -0.0029(17) -0.0114(18) C12 0.021(2) 0.030(2) 0.024(2) -0.0071(18) -0.0040(17) -0.0049(18) C13 0.026(2) 0.043(3) 0.035(3) -0.012(2) 0.0022(19) -0.007(2) C14 0.025(2) 0.071(4) 0.027(2) -0.015(2) 0.0085(19) -0.016(2) C15 0.035(3) 0.071(4) 0.023(2) 0.000(2) 0.001(2) -0.021(3) C16 0.037(2) 0.040(3) 0.029(3) 0.002(2) -0.003(2) -0.011(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1250 0.1230 '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 C1 S1 C8 91.65(19) N1 O1 H1 109.5 C11 N1 O1 114.0(3) C11 N1 C9 119.0(3) O1 N1 C9 112.5(3) C11 N2 H2A 120.0 C11 N2 H2B 120.0 H2A N2 H2B 120.0 C7 C8 C9 128.6(3) C7 C8 S1 112.2(3) C9 C8 S1 119.2(3) N1 C9 C8 109.6(3) N1 C9 C10 112.4(3) C8 C9 C10 112.4(3) N1 C9 H9 107.4 C8 C9 H9 107.4 C10 C9 H9 107.4 O2 C11 N2 122.4(4) O2 C11 N1 119.3(3) N2 C11 N1 118.2(3) C9 C10 H10A 109.5 C9 C10 H10B 109.5 H10A C10 H10B 109.5 C9 C10 H10C 109.5 H10A C10 H10C 109.5 H10B C10 H10C 109.5 C8 C7 C6 112.6(4) C8 C7 H7 123.7 C6 C7 H7 123.7 C1 C6 C5 119.3(4) C1 C6 C7 112.2(4) C5 C6 C7 128.5(4) C6 C1 C2 121.5(4) C6 C1 S1 111.4(3) C2 C1 S1 127.1(3) C3 C2 C1 118.2(4) C3 C2 H2 120.9 C1 C2 H2 120.9 C2 C3 C4 121.0(4) C2 C3 H3 119.5 C4 C3 H3 119.5 C5 C4 C3 120.9(4) C5 C4 H4 119.6 C3 C4 H4 119.6 C4 C5 C6 119.1(4) C4 C5 H5 120.4 C6 C5 H5 120.4 C12 S2 C19 91.37(19) N3 O3 H3A 109.7 C22 N3 O3 113.4(3) C22 N3 C20 117.8(3) O3 N3 C20 112.2(3) C22 N4 H4A 120.1 C22 N4 H4B 119.9 H4A N4 H4B 120.0 C18 C19 C20 128.0(3) C18 C19 S2 112.1(3) C20 C19 S2 119.7(3) N3 C20 C19 109.7(3) N3 C20 C21 112.8(3) C19 C20 C21 112.0(3) N3 C20 H20 107.4 C19 C20 H20 107.4 C21 C20 H20 107.4 O4 C22 N4 122.9(3) O4 C22 N3 119.1(3) N4 C22 N3 117.8(3) C20 C21 H21A 109.5 C20 C21 H21B 109.5 H21A C21 H21B 109.5 C20 C21 H21C 109.5 H21A C21 H21C 109.5 H21B C21 H21C 109.5 C19 C18 C17 113.4(4) C19 C18 H18 123.3 C17 C18 H18 123.3 C12 C17 C16 119.5(4) C12 C17 C18 111.7(4) C16 C17 C18 128.8(4) C17 C12 C13 120.8(4) C17 C12 S2 111.4(3) C13 C12 S2 127.7(4) C14 C13 C12 118.1(4) C14 C13 H13 121.0 C12 C13 H13 121.0 C13 C14 C15 121.5(4) C13 C14 H14 119.2 C15 C14 H14 119.2 C16 C15 C14 120.6(4) C16 C15 H15 119.7 C14 C15 H15 119.7 C15 C16 C17 119.5(5) C15 C16 H16 120.3 C17 C16 H16 120.3 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C1 1.741(4) S1 C8 1.753(4) O1 N1 1.420(4) O1 H1 0.8202 O2 C11 1.252(4) N1 C11 1.378(5) N1 C9 1.475(5) N2 C11 1.331(5) N2 H2A 0.8612 N2 H2B 0.8602 C8 C7 1.366(5) C8 C9 1.503(5) C9 C10 1.533(5) C9 H9 0.9800 C10 H10A 0.9600 C10 H10B 0.9600 C10 H10C 0.9600 C7 C6 1.451(5) C7 H7 0.9300 C6 C1 1.400(6) C6 C5 1.402(6) C1 C2 1.410(6) C2 C3 1.379(6) C2 H2 0.9300 C3 C4 1.400(7) C3 H3 0.9300 C4 C5 1.391(6) C4 H4 0.9300 C5 H5 0.9300 S2 C12 1.737(4) S2 C19 1.754(4) O3 N3 1.426(4) O3 H3A 0.8201 O4 C22 1.254(4) N3 C22 1.385(5) N3 C20 1.478(5) N4 C22 1.330(5) N4 H4A 0.8590 N4 H4B 0.8605 C19 C18 1.351(5) C19 C20 1.507(5) C20 C21 1.526(5) C20 H20 0.9800 C21 H21A 0.9600 C21 H21B 0.9600 C21 H21C 0.9600 C18 C17 1.443(5) C18 H18 0.9300 C17 C12 1.404(6) C17 C16 1.406(6) C12 C13 1.407(6) C13 C14 1.385(6) C13 H13 0.9300 C14 C15 1.391(7) C14 H14 0.9300 C15 C16 1.377(6) C15 H15 0.9300 C16 H16 0.9300 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O2 0.82 1.91 2.718(4) 166.1 1_455 N2 H2A O2 0.86 2.18 2.950(4) 148.1 2_776 N2 H2B O1 0.86 2.43 3.106(4) 135.7 2_666 O3 H3A O4 0.82 1.93 2.723(4) 162.7 1_655 N4 H4A O4 0.86 2.17 2.960(4) 151.8 2_467 N4 H4B O3 0.86 2.46 3.132(4) 135.8 2_577 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 C1 S1 C8 C7 1.1(3) C1 S1 C8 C9 178.0(3) C11 N1 C9 C8 -156.7(3) O1 N1 C9 C8 66.2(4) C11 N1 C9 C10 77.5(4) O1 N1 C9 C10 -59.6(4) C7 C8 C9 N1 -134.1(4) S1 C8 C9 N1 49.6(4) C7 C8 C9 C10 -8.4(6) S1 C8 C9 C10 175.3(3) O1 N1 C11 O2 168.1(3) C9 N1 C11 O2 31.5(5) O1 N1 C11 N2 -14.5(5) C9 N1 C11 N2 -151.0(3) C9 C8 C7 C6 -177.6(4) S1 C8 C7 C6 -1.1(4) C8 C7 C6 C1 0.5(5) C8 C7 C6 C5 -178.0(4) C5 C6 C1 C2 1.2(6) C7 C6 C1 C2 -177.4(4) C5 C6 C1 S1 179.0(3) C7 C6 C1 S1 0.4(4) C8 S1 C1 C6 -0.8(3) C8 S1 C1 C2 176.8(4) C6 C1 C2 C3 0.0(6) S1 C1 C2 C3 -177.4(3) C1 C2 C3 C4 -0.9(6) C2 C3 C4 C5 0.7(7) C3 C4 C5 C6 0.5(7) C1 C6 C5 C4 -1.4(6) C7 C6 C5 C4 177.0(4) C12 S2 C19 C18 0.9(3) C12 S2 C19 C20 177.9(3) C22 N3 C20 C19 -160.7(3) O3 N3 C20 C19 64.8(4) C22 N3 C20 C21 73.8(4) O3 N3 C20 C21 -60.7(4) C18 C19 C20 N3 -133.8(4) S2 C19 C20 N3 49.7(4) C18 C19 C20 C21 -7.7(5) S2 C19 C20 C21 175.8(3) O3 N3 C22 O4 168.4(3) C20 N3 C22 O4 34.4(5) O3 N3 C22 N4 -15.7(5) C20 N3 C22 N4 -149.6(3) C20 C19 C18 C17 -177.5(4) S2 C19 C18 C17 -0.8(4) C19 C18 C17 C12 0.2(5) C19 C18 C17 C16 -177.6(4) C16 C17 C12 C13 0.1(6) C18 C17 C12 C13 -177.9(4) C16 C17 C12 S2 178.5(3) C18 C17 C12 S2 0.5(4) C19 S2 C12 C17 -0.8(3) C19 S2 C12 C13 177.5(4) C17 C12 C13 C14 0.0(6) S2 C12 C13 C14 -178.1(3) C12 C13 C14 C15 -0.2(6) C13 C14 C15 C16 0.3(7) C14 C15 C16 C17 -0.1(7) C12 C17 C16 C15 -0.1(6) C18 C17 C16 C15 177.6(4)