#------------------------------------------------------------------------------ #$Date: 2019-11-17 09:21:32 +0200 (Sun, 17 Nov 2019) $ #$Revision: 229073 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229951.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_7229951 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, H2 O' _chemical_formula_sum 'C11 H14 N2 O3 S' _chemical_formula_weight 254.30 _space_group_crystal_system monoclinic _space_group_IT_number 7 _space_group_name_Hall 'P -2yc' _space_group_name_H-M_alt 'P 1 c 1' _symmetry_space_group_name_Hall 'P -2yc' _symmetry_space_group_name_H-M 'P 1 c 1' _atom_sites_solution_hydrogens mixed _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 90 _cell_angle_beta 95.637(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 20.997(3) _cell_length_b 6.1061(9) _cell_length_c 9.6195(14) _cell_measurement_reflns_used 9899 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 26.927 _cell_measurement_theta_min 2.925 _cell_volume 1227.3(3) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_unetI/netI 0.0701 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 5543 _diffrn_reflns_point_group_measured_fraction_full 0.991 _diffrn_reflns_point_group_measured_fraction_max 0.976 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.607 _diffrn_reflns_theta_min 2.925 _exptl_absorpt_coefficient_mu 0.262 _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.376 _exptl_crystal_description block _exptl_crystal_F_000 536 _refine_diff_density_max 1.142 _refine_diff_density_min -0.640 _refine_diff_density_rms 0.144 _refine_ls_abs_structure_details ; Flack x determined using 1857 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.26(6) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 356 _refine_ls_number_reflns 5543 _refine_ls_number_restraints 38 _refine_ls_restrained_S_all 1.113 _refine_ls_R_factor_all 0.1118 _refine_ls_R_factor_gt 0.0990 _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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2565 _refine_ls_wR_factor_ref 0.2685 _reflns_Friedel_coverage 0.971 _reflns_Friedel_fraction_full 0.986 _reflns_Friedel_fraction_max 0.963 _reflns_number_gt 4667 _reflns_number_total 5543 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ce02150j2.cif _cod_data_source_block t _cod_depositor_comments 'Adding full bibliography for 7229950--7229953.cif.' _cod_database_code 7229951 _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 ; t.res created by SHELXL-2014/7 TITL w P 1 c 1 R = 0.14 CELL 0.71073 20.997 6.1061 9.6195 90 95.637 90 ZERR 4 0.003 0.0009 0.0014 0 0.005 0 LATT -1 SYMM +X,-Y,0.5+Z 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 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 56 8 12 4 EQIV $1 +X,1+Y,+Z EQIV $2 +X,1-Y,-0.5+Z EQIV $3 +X,-Y,0.5+Z EQIV $4 +X,-1+Y,+Z EQIV $5 +X,1-Y,0.5+Z EQIV $6 +X,2-Y,0.5+Z DFIX 2.2 H5a H4b_$1 SADI C7 C8 C8 C7A SADI C18 C19 C19 C18A RIGU S1 S1A C7 C7A S2 S2A C18A C18 RIGU C3 C4 C5 ISOR 0.01 0.02 C7A C7 C18 C18A L.S. 5 PLAN -20 TEMP 23 HTAB N2 O6 HTAB O5 O1 HTAB O6 O3 HTAB N2 O6_$2 HTAB O3 O4_$3 HTAB N4 O5_$2 HTAB N4 O5_$4 HTAB O1 O2_$5 HTAB O6 O4_$5 HTAB O5 O2_$6 BOND $H CONF MORE -1 fmap 2 acta REM REM REM WGHT 0.200000 BASF 0.18715 FVAR 10.87190 0.59667 0.65396 PART 1 S1 5 0.231921 0.567027 0.488119 21.00000 0.03231 0.04213 = 0.05951 0.00882 0.00150 0.00400 PART 0 PART 2 S1A 5 0.186417 1.013660 0.398799 -21.00000 0.02527 0.03818 = 0.08150 0.02026 0.00988 0.01317 PART 0 O1 4 0.377748 0.737214 0.489474 11.00000 0.03810 0.02654 = 0.01773 0.00032 -0.00054 -0.00321 AFIX 147 H1 2 0.367734 0.644354 0.544938 11.00000 -1.50000 AFIX 0 O2 4 0.370570 0.621564 0.134046 11.00000 0.04427 0.03744 = 0.01547 -0.00458 0.00162 0.00054 N1 3 0.348213 0.689371 0.356053 11.00000 0.03065 0.02883 = 0.01885 -0.00239 -0.00254 0.00327 N2 3 0.446429 0.551325 0.311563 11.00000 0.03304 0.04954 = 0.02548 0.00093 0.00555 0.01097 AFIX 93 H2A 2 0.472290 0.502789 0.254754 11.00000 -1.20000 H2B 2 0.457906 0.553578 0.399868 11.00000 -1.20000 AFIX 0 C8 1 0.241191 0.807803 0.400473 11.00000 0.02585 0.03478 = 0.03217 -0.00594 -0.00243 0.00391 C9 1 0.296149 0.838279 0.310997 11.00000 0.03324 0.03059 = 0.02460 -0.00056 0.00173 0.00683 AFIX 13 H9 2 0.280338 0.797163 0.215314 11.00000 -1.20000 AFIX 0 C11 1 0.389273 0.622175 0.263349 11.00000 0.03040 0.02217 = 0.02385 -0.00019 0.00314 -0.00381 C10 1 0.318361 1.077265 0.306828 11.00000 0.05050 0.03689 = 0.04353 0.00951 0.00791 0.00402 AFIX 137 H10A 2 0.327005 1.131451 0.400463 11.00000 -1.50000 H10B 2 0.285407 1.164296 0.257532 11.00000 -1.50000 H10C 2 0.356576 1.085638 0.259878 11.00000 -1.50000 AFIX 0 PART 1 C7 1 0.191905 0.958549 0.420975 21.00000 0.03361 0.05020 = 0.03973 0.01240 0.00408 0.00404 AFIX 43 H7 2 0.188919 1.098905 0.383359 21.00000 -1.20000 AFIX 0 PART 0 PART 2 C7A 1 0.223669 0.628697 0.475646 -21.00000 0.05065 0.04542 = 0.02656 -0.00610 -0.00483 0.02068 AFIX 43 H7A 2 0.246658 0.498326 0.478395 -21.00000 -1.20000 AFIX 0 PART 0 C6 1 0.145806 0.862821 0.510252 11.00000 0.02764 0.06172 = 0.05405 -0.00629 0.00475 0.00494 C1 1 0.167224 0.655580 0.550254 11.00000 0.03161 0.05267 = 0.05217 0.00547 -0.00247 -0.01110 C2 1 0.133551 0.532642 0.640871 11.00000 0.07394 0.08403 = 0.08093 0.01565 -0.00102 -0.03204 AFIX 43 H2 2 0.147497 0.393239 0.668334 11.00000 -1.20000 AFIX 0 C3 1 0.080214 0.618637 0.688541 11.00000 0.05121 0.17042 = 0.07523 0.00937 0.01329 -0.03042 AFIX 43 H3 2 0.058463 0.538576 0.751197 11.00000 -1.20000 AFIX 0 C4 1 0.058034 0.818390 0.646808 11.00000 0.03757 0.17631 = 0.08210 -0.01258 0.01949 -0.01862 AFIX 43 H4 2 0.020376 0.869293 0.678875 11.00000 -1.20000 AFIX 0 C5 1 0.089447 0.950034 0.557890 11.00000 0.03110 0.12868 = 0.09772 -0.01186 0.01479 0.01858 AFIX 43 H5 2 0.074261 1.088285 0.531023 11.00000 -1.20000 AFIX 0 PART 1 S2 5 0.810901 0.504462 0.529468 31.00000 0.03463 0.04496 = 0.09111 0.01140 -0.01124 -0.01263 PART 0 PART 2 S2A 5 0.763192 0.052673 0.598618 -31.00000 0.02588 0.02679 = 0.04971 0.01170 -0.00028 -0.00228 PART 0 O3 4 0.616664 0.238145 0.539563 11.00000 0.03167 0.03169 = 0.02103 0.00189 0.01057 0.00307 AFIX 147 H3A 2 0.621866 0.135457 0.594437 11.00000 -1.50000 AFIX 0 O4 4 0.625285 0.121892 0.188127 11.00000 0.04466 0.03193 = 0.02131 -0.00518 0.01028 -0.00585 N3 3 0.647588 0.191510 0.418192 11.00000 0.03352 0.02673 = 0.01945 -0.00675 0.00803 -0.00307 N4 3 0.548791 0.050942 0.333405 11.00000 0.04244 0.04931 = 0.02684 -0.00103 0.00134 -0.00897 AFIX 93 H4A 2 0.522939 -0.000275 0.266363 11.00000 -1.20000 H4B 2 0.537525 0.055063 0.416937 11.00000 -1.20000 AFIX 0 C19 1 0.753616 0.307216 0.506939 11.00000 0.03019 0.03241 = 0.03519 -0.00231 0.01308 -0.00346 C20 1 0.698875 0.343493 0.396539 11.00000 0.03874 0.03612 = 0.02144 -0.00014 0.00562 -0.00429 AFIX 13 H20 2 0.714344 0.306102 0.306655 11.00000 -1.20000 AFIX 0 C22 1 0.606022 0.123554 0.307982 11.00000 0.03583 0.02359 = 0.01991 0.00312 0.00333 0.00493 C21 1 0.676433 0.581524 0.386449 11.00000 0.05786 0.02960 = 0.04637 0.00808 -0.00777 -0.00563 AFIX 137 H21A 2 0.635464 0.588915 0.332747 11.00000 -1.50000 H21B 2 0.706840 0.667371 0.341707 11.00000 -1.50000 H21C 2 0.672897 0.637829 0.478551 11.00000 -1.50000 AFIX 0 PART 1 C18A 1 0.765806 0.125409 0.585513 31.00000 0.01978 0.04545 = 0.04846 0.01260 0.00589 0.00627 AFIX 43 H18A 2 0.739728 0.001985 0.580038 31.00000 -1.20000 AFIX 0 PART 0 PART 2 C18 1 0.803867 0.427617 0.555167 -31.00000 0.06815 0.05493 = 0.07758 0.02895 0.01491 0.00417 AFIX 43 H18 2 0.807532 0.569024 0.520932 -31.00000 -1.20000 AFIX 0 PART 0 C12 1 0.827850 0.145505 0.685360 11.00000 0.04287 0.05163 = 0.05044 -0.00089 0.01741 -0.00388 C17 1 0.852558 0.348178 0.657721 11.00000 0.03439 0.04030 = 0.06180 -0.00360 0.00134 -0.00374 C16 1 0.910200 0.410150 0.732961 11.00000 0.03860 0.09163 = 0.11194 0.01273 -0.02412 -0.02310 AFIX 43 H16 2 0.927824 0.545692 0.714856 11.00000 -1.20000 AFIX 0 C15 1 0.940411 0.282384 0.828899 11.00000 0.03656 0.12970 = 0.09888 0.00947 -0.01918 -0.01989 AFIX 43 H15 2 0.979016 0.326869 0.876128 11.00000 -1.20000 AFIX 0 C14 1 0.913365 0.076146 0.859321 11.00000 0.05783 0.13752 = 0.07370 0.04380 0.01015 0.04160 AFIX 43 H14 2 0.932743 -0.011832 0.930231 11.00000 -1.20000 AFIX 0 C13 1 0.857785 0.008396 0.781810 11.00000 0.05044 0.05920 = 0.08846 0.01380 0.01758 0.00565 AFIX 43 H13 2 0.841091 -0.130068 0.795748 11.00000 -1.20000 AFIX 6 O5 4 0.467402 1.062155 0.569240 11.00000 0.03184 0.03440 = 0.03724 -0.00327 0.00322 -0.00077 H5A 2 0.452063 0.957231 0.518401 11.00000 -1.50000 H5B 2 0.458855 1.183074 0.527775 11.00000 -1.50000 AFIX 6 O6 4 0.526432 0.563329 0.581482 11.00000 0.03383 0.03404 = 0.04406 -0.00694 0.00403 0.00084 H6A 2 0.546841 0.682750 0.575906 11.00000 -1.50000 H6B 2 0.550232 0.456720 0.562867 11.00000 -1.50000 AFIX 0 HKLF 5 REM w P 1 c 1 R = 0.14 REM R1 = 0.0990 for 4667 Fo > 4sig(Fo) and 0.1118 for all 5543 data REM 356 parameters refined using 38 restraints END WGHT 0.2000 0.0000 REM Highest difference peak 1.142, deepest hole -0.640, 1-sigma level 0.144 Q1 1 0.7656 -0.0659 0.6752 11.00000 0.05 1.14 Q2 1 0.2339 0.4297 0.4183 11.00000 0.05 0.95 Q3 1 0.3797 0.6234 0.6936 11.00000 0.05 0.86 Q4 1 0.3755 1.2577 0.4223 11.00000 0.05 0.75 Q5 1 0.4659 0.9336 0.6285 11.00000 0.05 0.72 Q6 1 0.7581 0.6958 0.5860 11.00000 0.05 0.68 Q7 1 0.3438 1.2991 0.2863 11.00000 0.05 0.64 Q8 1 0.6206 -0.1163 0.2562 11.00000 0.05 0.63 Q9 1 0.1811 1.0047 0.3210 11.00000 0.05 0.62 Q10 1 0.2410 1.2079 0.3271 11.00000 0.05 0.62 Q11 1 0.5234 0.4334 0.5170 11.00000 0.05 0.60 Q12 1 0.7058 0.6722 0.4599 11.00000 0.05 0.59 Q13 1 0.6208 0.2502 0.1048 11.00000 0.05 0.56 Q14 1 0.6228 0.7637 0.4773 11.00000 0.05 0.51 Q15 1 0.3187 0.9409 0.2399 11.00000 0.05 0.51 Q16 1 0.2441 0.4177 0.5383 11.00000 0.05 0.48 Q17 1 0.2378 0.9410 0.5829 11.00000 0.05 0.48 Q18 1 0.8045 0.4951 0.6051 11.00000 0.05 0.48 Q19 1 0.0757 0.4320 0.6030 11.00000 0.05 0.47 Q20 1 0.5209 0.4368 0.6561 11.00000 0.05 0.46 ; _shelx_res_checksum 12519 loop_ _space_group_symop_operation_xyz 'x, y, z' 'x, -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 S1 S 0.2319(3) 0.5670(11) 0.4881(7) 0.0448(15) Uani 0.597(12) 1 d . . P A 1 S1A S 0.1864(5) 1.0137(17) 0.3988(14) 0.048(3) Uani 0.403(12) 1 d . . P A 2 O1 O 0.3777(2) 0.7372(7) 0.4895(4) 0.0277(9) Uani 1 1 d . . . . . H1 H 0.3677 0.6444 0.5449 0.042 Uiso 1 1 calc R U . . . O2 O 0.3706(3) 0.6216(8) 0.1340(4) 0.0325(10) Uani 1 1 d . . . . . N1 N 0.3482(3) 0.6894(9) 0.3561(5) 0.0264(11) Uani 1 1 d . . . . . N2 N 0.4464(3) 0.5513(10) 0.3116(6) 0.0358(13) Uani 1 1 d . . . . . H2A H 0.4723 0.5028 0.2548 0.043 Uiso 1 1 calc R U . . . H2B H 0.4579 0.5536 0.3999 0.043 Uiso 1 1 calc R U . . . C8 C 0.2412(3) 0.8078(11) 0.4005(7) 0.0313(13) Uani 1 1 d D . . . . C9 C 0.2961(3) 0.8383(10) 0.3110(7) 0.0296(13) Uani 1 1 d . . . . . H9 H 0.2803 0.7972 0.2153 0.035 Uiso 1 1 calc R U . . . C11 C 0.3893(3) 0.6222(9) 0.2633(6) 0.0254(12) Uani 1 1 d . . . . . C10 C 0.3184(4) 1.0773(12) 0.3068(9) 0.0434(17) Uani 1 1 d . . . . . H10A H 0.3270 1.1315 0.4005 0.065 Uiso 1 1 calc R U . . . H10B H 0.2854 1.1643 0.2575 0.065 Uiso 1 1 calc R U . . . H10C H 0.3566 1.0856 0.2599 0.065 Uiso 1 1 calc R U . . . C7 C 0.1919(14) 0.959(4) 0.421(3) 0.041(6) Uani 0.597(12) 1 d D U P A 1 H7 H 0.1889 1.0989 0.3834 0.049 Uiso 0.597(12) 1 calc R U P A 1 C7A C 0.2237(18) 0.629(5) 0.476(3) 0.041(9) Uani 0.403(12) 1 d D U P A 2 H7A H 0.2467 0.4983 0.4784 0.050 Uiso 0.403(12) 1 calc R U P A 2 C6 C 0.1458(4) 0.8628(15) 0.5103(10) 0.0478(19) Uani 1 1 d . . . . . C1 C 0.1672(4) 0.6556(14) 0.5503(9) 0.0459(18) Uani 1 1 d . . . . . C2 C 0.1336(6) 0.533(2) 0.6409(15) 0.080(4) Uani 1 1 d . . . . . H2 H 0.1475 0.3932 0.6683 0.096 Uiso 1 1 calc R U . . . C3 C 0.0802(7) 0.619(4) 0.6885(16) 0.098(4) Uani 1 1 d . U . . . H3 H 0.0585 0.5386 0.7512 0.118 Uiso 1 1 calc R U . . . C4 C 0.0580(6) 0.818(4) 0.6468(16) 0.098(4) Uani 1 1 d . U . . . H4 H 0.0204 0.8693 0.6789 0.117 Uiso 1 1 calc R U . . . C5 C 0.0894(5) 0.950(3) 0.5579(16) 0.085(4) Uani 1 1 d . U . . . H5 H 0.0743 1.0883 0.5310 0.102 Uiso 1 1 calc R U . . . S2 S 0.81090(19) 0.5045(8) 0.5295(5) 0.0581(14) Uani 0.654(11) 1 d . . P B 1 S2A S 0.7632(5) 0.0527(15) 0.5986(12) 0.034(2) Uani 0.346(11) 1 d . . P B 2 O3 O 0.6167(2) 0.2381(8) 0.5396(4) 0.0276(9) Uani 1 1 d . . . . . H3A H 0.6219 0.1355 0.5944 0.041 Uiso 1 1 calc R U . . . O4 O 0.6253(3) 0.1219(7) 0.1881(5) 0.0322(10) Uani 1 1 d . . . . . N3 N 0.6476(3) 0.1915(8) 0.4182(5) 0.0262(11) Uani 1 1 d . . . . . N4 N 0.5488(3) 0.0509(11) 0.3334(6) 0.0397(14) Uani 1 1 d . . . . . H4A H 0.5229 -0.0003 0.2664 0.048 Uiso 1 1 calc R U . . . H4B H 0.5375 0.0551 0.4169 0.048 Uiso 1 1 calc R U . . . C19 C 0.7536(3) 0.3072(11) 0.5069(7) 0.0319(14) Uani 1 1 d D . . . . C20 C 0.6989(4) 0.3435(11) 0.3965(7) 0.0319(14) Uani 1 1 d . . . . . H20 H 0.7143 0.3061 0.3067 0.038 Uiso 1 1 calc R U . . . C22 C 0.6060(3) 0.1236(10) 0.3080(6) 0.0264(12) Uani 1 1 d . . . . . C21 C 0.6764(4) 0.5815(12) 0.3864(9) 0.0455(19) Uani 1 1 d . . . . . H21A H 0.6355 0.5889 0.3327 0.068 Uiso 1 1 calc R U . . . H21B H 0.7068 0.6674 0.3417 0.068 Uiso 1 1 calc R U . . . H21C H 0.6729 0.6378 0.4786 0.068 Uiso 1 1 calc R U . . . C18A C 0.7658(11) 0.125(4) 0.586(3) 0.038(5) Uani 0.654(11) 1 d D U P B 1 H18A H 0.7397 0.0020 0.5800 0.045 Uiso 0.654(11) 1 calc R U P B 1 C18 C 0.8039(17) 0.428(6) 0.555(4) 0.066(11) Uani 0.346(11) 1 d D U P B 2 H18 H 0.8075 0.5690 0.5209 0.080 Uiso 0.346(11) 1 calc R U P B 2 C12 C 0.8278(4) 0.1455(15) 0.6854(9) 0.0475(19) Uani 1 1 d . . . . . C17 C 0.8526(4) 0.3482(13) 0.6577(10) 0.0457(18) Uani 1 1 d . . . . . C16 C 0.9102(5) 0.410(2) 0.7330(17) 0.083(4) Uani 1 1 d . . . . . H16 H 0.9278 0.5457 0.7149 0.099 Uiso 1 1 calc R U . . . C15 C 0.9404(5) 0.282(3) 0.8289(17) 0.090(4) Uani 1 1 d . . . . . H15 H 0.9790 0.3269 0.8761 0.108 Uiso 1 1 calc R U . . . C14 C 0.9134(6) 0.076(3) 0.8593(14) 0.089(5) Uani 1 1 d . . . . . H14 H 0.9327 -0.0118 0.9302 0.107 Uiso 1 1 calc R U . . . C13 C 0.8578(5) 0.0084(18) 0.7818(14) 0.065(3) Uani 1 1 d . . . . . H13 H 0.8411 -0.1301 0.7957 0.078 Uiso 1 1 calc R U . . . O5 O 0.4674(2) 1.0622(8) 0.5692(5) 0.0345(11) Uani 1 1 d G . . . . H5A H 0.4521 0.9572 0.5184 0.052 Uiso 1 1 d DG U . . . H5B H 0.4589 1.1831 0.5278 0.052 Uiso 1 1 d G U . . . O6 O 0.5264(2) 0.5633(8) 0.5815(6) 0.0373(11) Uani 1 1 d G . . . . H6A H 0.5468 0.6827 0.5759 0.056 Uiso 1 1 d G U . . . H6B H 0.5502 0.4567 0.5629 0.056 Uiso 1 1 d G 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 0.032(2) 0.042(3) 0.060(3) 0.009(2) 0.0015(17) 0.004(2) S1A 0.025(3) 0.038(4) 0.081(7) 0.020(3) 0.010(3) 0.013(2) O1 0.038(2) 0.027(2) 0.0177(18) 0.0003(15) -0.0005(17) -0.0032(18) O2 0.044(3) 0.037(2) 0.0155(19) -0.0046(17) 0.0016(18) 0.001(2) N1 0.031(3) 0.029(2) 0.019(2) -0.0024(18) -0.0025(19) 0.003(2) N2 0.033(3) 0.050(3) 0.025(3) 0.001(2) 0.006(2) 0.011(2) C8 0.026(3) 0.035(3) 0.032(3) -0.006(3) -0.002(2) 0.004(3) C9 0.033(3) 0.031(3) 0.025(3) -0.001(2) 0.002(2) 0.007(2) C11 0.030(3) 0.022(2) 0.024(3) 0.000(2) 0.003(2) -0.004(2) C10 0.051(4) 0.037(4) 0.044(4) 0.010(3) 0.008(3) 0.004(3) C7 0.034(10) 0.050(13) 0.040(8) 0.012(9) 0.004(6) 0.004(8) C7A 0.051(13) 0.045(14) 0.027(10) -0.006(10) -0.005(8) 0.021(10) C6 0.028(4) 0.062(5) 0.054(5) -0.006(4) 0.005(3) 0.005(3) C1 0.032(4) 0.053(4) 0.052(4) 0.005(4) -0.002(3) -0.011(3) C2 0.074(8) 0.084(8) 0.081(8) 0.016(6) -0.001(6) -0.032(6) C3 0.051(6) 0.170(12) 0.075(8) 0.009(8) 0.013(6) -0.030(7) C4 0.038(5) 0.176(12) 0.082(8) -0.013(8) 0.019(5) -0.019(6) C5 0.031(4) 0.129(9) 0.098(8) -0.012(7) 0.015(5) 0.019(5) S2 0.0346(18) 0.045(2) 0.091(3) 0.011(2) -0.0112(17) -0.0126(15) S2A 0.026(3) 0.027(4) 0.050(4) 0.012(3) 0.000(2) -0.002(3) O3 0.032(2) 0.032(2) 0.0210(19) 0.0019(15) 0.0106(16) 0.0031(18) O4 0.045(3) 0.032(2) 0.021(2) -0.0052(17) 0.0103(19) -0.0059(19) N3 0.034(3) 0.027(2) 0.019(2) -0.0067(19) 0.008(2) -0.003(2) N4 0.042(3) 0.049(3) 0.027(3) -0.001(2) 0.001(2) -0.009(3) C19 0.030(3) 0.032(3) 0.035(3) -0.002(3) 0.013(3) -0.003(3) C20 0.039(3) 0.036(3) 0.021(3) 0.000(2) 0.006(2) -0.004(3) C22 0.036(3) 0.024(3) 0.020(3) 0.003(2) 0.003(2) 0.005(2) C21 0.058(5) 0.030(3) 0.046(4) 0.008(3) -0.008(4) -0.006(3) C18A 0.020(6) 0.045(10) 0.048(8) 0.013(8) 0.006(5) 0.006(8) C18 0.068(16) 0.055(15) 0.078(15) 0.029(12) 0.015(11) 0.004(12) C12 0.043(4) 0.052(4) 0.050(5) -0.001(3) 0.017(4) -0.004(3) C17 0.034(4) 0.040(4) 0.062(5) -0.004(3) 0.001(3) -0.004(3) C16 0.039(5) 0.092(8) 0.112(10) 0.013(7) -0.024(6) -0.023(5) C15 0.037(5) 0.130(12) 0.099(9) 0.009(9) -0.019(5) -0.020(6) C14 0.058(7) 0.138(12) 0.074(8) 0.044(8) 0.010(6) 0.042(8) C13 0.050(5) 0.059(6) 0.088(7) 0.014(5) 0.018(5) 0.006(4) O5 0.032(2) 0.034(2) 0.037(2) -0.0033(19) 0.003(2) -0.0008(19) O6 0.034(3) 0.034(2) 0.044(3) -0.007(2) 0.004(2) 0.0008(19) 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 92.0(5) C8 S1A C6 88.5(6) N1 O1 H1 109.5 C11 N1 O1 114.3(5) C11 N1 C9 119.9(5) O1 N1 C9 113.3(5) C11 N2 H2A 120.0 C11 N2 H2B 120.0 H2A N2 H2B 120.0 C7A C8 C9 130.6(16) C7 C8 C9 127.4(13) C7A C8 S1A 112.0(16) C9 C8 S1A 117.0(6) C7 C8 S1 111.7(12) C9 C8 S1 120.9(5) N1 C9 C8 110.2(5) N1 C9 C10 112.4(6) C8 C9 C10 112.4(6) N1 C9 H9 107.2 C8 C9 H9 107.2 C10 C9 H9 107.2 O2 C11 N2 121.9(6) O2 C11 N1 119.2(6) N2 C11 N1 118.8(6) 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 110.7(17) C8 C7 H7 124.6 C6 C7 H7 124.6 C8 C7A C1 116(2) C8 C7A H7A 121.9 C1 C7A H7A 121.9 C1 C6 C5 120.9(10) C1 C6 C7 108.1(11) C5 C6 C7 131.0(14) C1 C6 S1A 120.0(7) C5 C6 S1A 119.1(10) C6 C1 C2 119.7(10) C6 C1 C7A 103.0(13) C2 C1 C7A 137.4(14) C6 C1 S1 117.5(7) C2 C1 S1 122.9(9) C3 C2 C1 119.3(14) C3 C2 H2 120.4 C1 C2 H2 120.4 C4 C3 C2 121.4(14) C4 C3 H3 119.3 C2 C3 H3 119.3 C3 C4 C5 122.3(13) C3 C4 H4 118.8 C5 C4 H4 118.8 C4 C5 C6 116.4(14) C4 C5 H5 121.8 C6 C5 H5 121.8 C19 S2 C17 90.1(4) C12 S2A C19 89.9(6) N3 O3 H3A 109.5 C22 N3 O3 112.9(5) C22 N3 C20 120.5(5) O3 N3 C20 113.3(5) C22 N4 H4A 120.0 C22 N4 H4B 120.0 H4A N4 H4B 120.0 C18 C19 C20 133.6(18) C18A C19 C20 127.2(12) C18A C19 S2 114.7(11) C20 C19 S2 117.9(5) C18 C19 S2A 105.1(18) C20 C19 S2A 121.2(6) N3 C20 C19 109.3(5) N3 C20 C21 112.9(6) C19 C20 C21 113.3(6) N3 C20 H20 107.0 C19 C20 H20 107.0 C21 C20 H20 107.0 O4 C22 N4 123.0(6) O4 C22 N3 118.3(6) N4 C22 N3 118.6(6) 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 C18A C12 112.6(16) C19 C18A H18A 123.7 C12 C18A H18A 123.7 C19 C18 C17 123(3) C19 C18 H18 118.7 C17 C18 H18 118.7 C13 C12 C17 121.9(9) C13 C12 C18A 132.9(11) C17 C12 C18A 105.2(10) C13 C12 S2A 116.3(8) C17 C12 S2A 121.7(8) C12 C17 C16 117.8(9) C12 C17 C18 100.4(15) C16 C17 C18 141.8(16) C12 C17 S2 117.4(7) C16 C17 S2 124.8(8) C15 C16 C17 122.2(12) C15 C16 H16 118.9 C17 C16 H16 118.9 C16 C15 C14 119.5(11) C16 C15 H15 120.3 C14 C15 H15 120.3 C13 C14 C15 119.1(10) C13 C14 H14 120.5 C15 C14 H14 120.5 C12 C13 C14 119.5(11) C12 C13 H13 120.2 C14 C13 H13 120.2 H5A O5 H5B 109.5 H6A O6 H6B 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C1 1.629(11) S1 C8 1.715(9) S1A C8 1.703(12) S1A C6 1.704(15) O1 N1 1.400(6) O1 H1 0.8200 O2 C11 1.267(8) N1 C11 1.363(8) N1 C9 1.455(8) N2 C11 1.317(9) N2 H2A 0.8600 N2 H2B 0.8600 C8 C7A 1.38(3) C8 C7 1.41(3) C8 C9 1.517(9) C9 C10 1.534(10) C9 H9 0.9800 C10 H10A 0.9600 C10 H10B 0.9600 C10 H10C 0.9600 C7 C6 1.48(3) C7 H7 0.9300 C7A C1 1.45(4) C7A H7A 0.9300 C6 C1 1.385(13) C6 C5 1.414(13) C1 C2 1.394(15) C2 C3 1.36(2) C2 H2 0.9300 C3 C4 1.35(3) C3 H3 0.9300 C4 C5 1.39(2) C4 H4 0.9300 C5 H5 0.9300 S2 C19 1.701(7) S2 C17 1.728(10) S2A C12 1.624(14) S2A C19 1.789(12) O3 N3 1.419(6) O3 H3A 0.8200 O4 C22 1.259(8) N3 C22 1.370(8) N3 C20 1.452(8) N4 C22 1.326(10) N4 H4A 0.8600 N4 H4B 0.8600 C19 C18 1.33(3) C19 C18A 1.35(2) C19 C20 1.503(10) C20 C21 1.528(10) C20 H20 0.9800 C21 H21A 0.9600 C21 H21B 0.9600 C21 H21C 0.9600 C18A C12 1.55(3) C18A H18A 0.9300 C18 C17 1.43(4) C18 H18 0.9300 C12 C13 1.357(15) C12 C17 1.378(12) C17 C16 1.400(13) C16 C15 1.32(2) C16 H16 0.9300 C15 C14 1.42(2) C15 H15 0.9300 C14 C13 1.38(2) C14 H14 0.9300 C13 H13 0.9300 O5 H5A 0.8499 O5 H5B 0.8499 O6 H6A 0.8502 O6 H6B 0.8504 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 N2 H2B O6 0.86 2.15 2.952(8) 154.5 . O5 H5A O1 0.85 2.06 2.790(6) 144.1 . O6 H6B O3 0.85 1.96 2.801(7) 170.2 . N2 H2A O6 0.86 2.15 2.990(8) 166.9 2_564 O3 H3A O4 0.82 1.81 2.619(6) 168.8 2 N4 H4A O5 0.86 2.16 3.000(8) 165.6 2_564 N4 H4B O5 0.86 2.18 2.972(8) 153.6 1_545 O1 H1 O2 0.82 1.83 2.607(6) 156.6 2_565 O6 H6A O4 0.85 2.23 2.939(7) 141.5 2_565 O5 H5B O2 0.85 2.51 2.916(7) 110.7 2_575 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 C6 S1A C8 C7A 4.8(17) C6 S1A C8 C9 179.1(6) C1 S1 C8 C7 -0.3(14) C1 S1 C8 C9 -178.8(6) C11 N1 C9 C8 153.4(5) O1 N1 C9 C8 -66.9(7) C11 N1 C9 C10 -80.4(8) O1 N1 C9 C10 59.3(7) C7A C8 C9 N1 -25(2) C7 C8 C9 N1 158.7(16) S1A C8 C9 N1 161.8(7) S1 C8 C9 N1 -23.0(8) C7A C8 C9 C10 -151.4(19) C7 C8 C9 C10 32.5(17) S1A C8 C9 C10 35.6(9) S1 C8 C9 C10 -149.3(6) O1 N1 C11 O2 -164.4(5) C9 N1 C11 O2 -25.1(9) O1 N1 C11 N2 18.3(8) C9 N1 C11 N2 157.6(6) C9 C8 C7 C6 177.3(9) S1 C8 C7 C6 -1(2) C9 C8 C7A C1 -179.6(12) S1A C8 C7A C1 -6(3) C8 C7 C6 C1 2(2) C8 C7 C6 C5 -179.6(13) C8 S1A C6 C1 -2.6(10) C8 S1A C6 C5 179.0(9) C5 C6 C1 C2 -1.3(15) C7 C6 C1 C2 177.1(15) S1A C6 C1 C2 -179.6(10) C5 C6 C1 C7A 178.1(16) S1A C6 C1 C7A -0.3(17) C5 C6 C1 S1 179.0(9) C7 C6 C1 S1 -2.6(15) C8 C7A C1 C6 4(3) C8 C7A C1 C2 -176.7(13) C8 S1 C1 C6 1.8(8) C8 S1 C1 C2 -178.0(9) C6 C1 C2 C3 -0.1(17) C7A C1 C2 C3 -179(2) S1 C1 C2 C3 179.7(11) C1 C2 C3 C4 2(2) C2 C3 C4 C5 -3(3) C3 C4 C5 C6 1(2) C1 C6 C5 C4 0.7(18) C7 C6 C5 C4 -177.3(18) S1A C6 C5 C4 179.1(11) C17 S2 C19 C18A -3.3(12) C17 S2 C19 C20 -178.5(6) C12 S2A C19 C18 2(2) C12 S2A C19 C20 179.0(6) C22 N3 C20 C19 -152.2(6) O3 N3 C20 C19 69.6(7) C22 N3 C20 C21 80.8(7) O3 N3 C20 C21 -57.4(7) C18 C19 C20 N3 -162(3) C18A C19 C20 N3 20.7(15) S2 C19 C20 N3 -164.7(5) S2A C19 C20 N3 22.0(9) C18 C19 C20 C21 -35(3) C18A C19 C20 C21 147.5(14) S2 C19 C20 C21 -37.9(8) S2A C19 C20 C21 148.8(7) O3 N3 C22 O4 165.3(5) C20 N3 C22 O4 26.9(8) O3 N3 C22 N4 -18.5(8) C20 N3 C22 N4 -156.8(6) C20 C19 C18A C12 178.2(9) S2 C19 C18A C12 3.5(19) C20 C19 C18 C17 -176.0(16) S2A C19 C18 C17 1(4) C19 C18A C12 C13 179.3(12) C19 C18A C12 C17 -1.8(18) C19 S2A C12 C13 178.8(8) C19 S2A C12 C17 -4.2(10) C13 C12 C17 C16 -0.1(15) C18A C12 C17 C16 -179.2(13) S2A C12 C17 C16 -176.9(11) C13 C12 C17 C18 -178(2) S2A C12 C17 C18 5(2) C13 C12 C17 S2 178.4(8) C18A C12 C17 S2 -0.7(13) C19 C18 C17 C12 -3(4) C19 C18 C17 C16 179.1(18) C19 S2 C17 C12 2.2(8) C19 S2 C17 C16 -179.4(11) C12 C17 C16 C15 -1(2) C18 C17 C16 C15 177(3) S2 C17 C16 C15 -179.1(13) C17 C16 C15 C14 -1(3) C16 C15 C14 C13 4(2) C17 C12 C13 C14 2.7(16) C18A C12 C13 C14 -178.5(15) S2A C12 C13 C14 179.7(11) C15 C14 C13 C12 -4.5(19)