#------------------------------------------------------------------------------ #$Date: 2018-01-12 04:40:18 +0200 (Fri, 12 Jan 2018) $ #$Revision: 205103 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229953.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_7229953 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_name_full CrystEngComm _journal_paper_doi 10.1039/C7CE02150J _journal_year 2018 _chemical_formula_moiety 'C11 H12 N2 O2 S, 2(C6 H6 N2 O)' _chemical_formula_sum 'C23 H24 N6 O4 S' _chemical_formula_weight 480.54 _chemical_name_systematic ; ? ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2017-09-05 _audit_creation_method ; Olex2 1.2 (compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320) ; _audit_update_record ; 2017-12-05 deposited with the CCDC. 2018-01-11 downloaded from the CCDC. ; _cell_angle_alpha 90.00 _cell_angle_beta 104.691(12) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.1859(7) _cell_length_b 43.799(5) _cell_length_c 10.7366(15) _cell_measurement_reflns_used 1855 _cell_measurement_temperature 213.0 _cell_measurement_theta_max 22.8460 _cell_measurement_theta_min 4.0170 _cell_volume 2359.0(5) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'XS (Sheldrick, 2008)' _diffrn_ambient_temperature 213.0 _diffrn_detector_area_resol_mean 10.4471 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 20.00 85.25 0.7500 40.0000 omega____ theta____ kappa____ phi______ frames - 15.2428 57.0000 0.0000 87 #__ type_ start__ end____ width___ exp.time_ 2 omega -39.00 39.00 0.7500 40.0000 omega____ theta____ kappa____ phi______ frames - 15.2428 -37.0000 -150.0000 104 #__ type_ start__ end____ width___ exp.time_ 3 omega 27.00 52.50 0.7500 40.0000 omega____ theta____ kappa____ phi______ frames - 15.2428 19.0000 0.0000 34 #__ type_ start__ end____ width___ exp.time_ 4 omega -47.00 -11.00 0.7500 40.0000 omega____ theta____ kappa____ phi______ frames - 15.2428 -37.0000 -180.0000 48 #__ type_ start__ end____ width___ exp.time_ 5 omega -25.00 0.50 0.7500 40.0000 omega____ theta____ kappa____ phi______ frames - -16.1803 -99.0000 90.0000 34 #__ type_ start__ end____ width___ exp.time_ 6 omega -17.00 16.00 0.7500 40.0000 omega____ theta____ kappa____ phi______ frames - -16.1803 -87.0000 132.0000 44 ; _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0472865000 _diffrn_orient_matrix_UB_12 -0.0142515000 _diffrn_orient_matrix_UB_13 0.0169984000 _diffrn_orient_matrix_UB_21 -0.0578927000 _diffrn_orient_matrix_UB_22 -0.0029818000 _diffrn_orient_matrix_UB_23 -0.0658380000 _diffrn_orient_matrix_UB_31 0.1189826000 _diffrn_orient_matrix_UB_32 -0.0070970000 _diffrn_orient_matrix_UB_33 -0.0065852000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0688 _diffrn_reflns_av_unetI/netI 0.1022 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 40 _diffrn_reflns_limit_k_min -54 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 14099 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 3.04 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.180 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.19389 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_description rodlike _exptl_crystal_F_000 1008 _refine_diff_density_max 0.512 _refine_diff_density_min -0.697 _refine_diff_density_rms 0.064 _refine_ls_extinction_coef 0.0057(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 311 _refine_ls_number_reflns 4806 _refine_ls_number_restraints 65 _refine_ls_restrained_S_all 1.133 _refine_ls_R_factor_all 0.1654 _refine_ls_R_factor_gt 0.0882 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0940P)^2^+1.9215P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2056 _refine_ls_wR_factor_ref 0.2634 _reflns_number_gt 2415 _reflns_number_total 4806 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL g170904a in Pn #7 New: P21/c CELL 0.71073 5.1859 43.799 10.7366 90 104.691 90 ZERR 4 0.0007 0.005 0.0015 0 0.012 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O S UNIT 92 96 24 16 4 EQIV $1 -X,-Y,-Z EQIV $2 -1+X,+Y,-1+Z EQIV $3 1+X,0.5-Y,-0.5+Z DELU 0.005 0.002 C8 C7 C6 C5 C4 C3 C2 C1 SIMU 0.005 0.004 2 C8 C7 C6 C5 C4 C3 C2 C1 L.S. 40 PLAN -20 TEMP 22.51(10) HTAB N2 O2_$1 HTAB O1 N6_$2 HTAB N3 O4_$3 BOND $H CONF fmap 2 acta SHEL 999 0.8 REM REM REM WGHT 0.094000 1.921500 EXTI 0.005722 FVAR 1.21845 C11 1 0.043453 0.044826 0.050828 11.00000 0.02972 0.04031 = 0.04577 0.00069 0.00397 0.00363 C9 1 -0.029018 0.085449 0.192099 11.00000 0.03394 0.03645 = 0.05398 -0.00093 0.00846 0.00126 AFIX 13 H9 2 -0.203862 0.075909 0.182661 11.00000 -1.20000 AFIX 0 C10 1 -0.072121 0.119867 0.189540 11.00000 0.04648 0.04180 = 0.08240 -0.00589 0.01134 0.00337 AFIX 137 H10A 2 -0.131553 0.125887 0.263627 11.00000 -1.50000 H10B 2 -0.204382 0.125365 0.112730 11.00000 -1.50000 H10C 2 0.092405 0.130043 0.190647 11.00000 -1.50000 AFIX 0 C8 1 0.147438 0.074175 0.316145 11.00000 0.04292 0.04982 = 0.05842 0.00371 0.01387 0.01105 C7 1 0.098273 0.051083 0.386942 11.00000 0.08231 0.07994 = 0.09218 0.03479 -0.00195 0.00252 AFIX 43 H7 2 -0.057411 0.039596 0.363848 11.00000 -1.20000 AFIX 0 C6 1 0.303031 0.045275 0.501236 11.00000 0.10346 0.10099 = 0.08065 0.03252 -0.00010 0.02234 C5 1 0.317322 0.023028 0.599894 11.00000 0.13964 0.12972 = 0.10421 0.05364 -0.00490 0.02545 AFIX 43 H5 2 0.179272 0.009212 0.595870 11.00000 -1.20000 AFIX 0 C4 1 0.541153 0.022648 0.700947 11.00000 0.14625 0.13980 = 0.07980 0.03796 0.00238 0.05009 AFIX 43 H4 2 0.558069 0.007221 0.762009 11.00000 -1.20000 AFIX 0 C3 1 0.726915 0.042408 0.715158 11.00000 0.13940 0.15208 = 0.05836 0.00749 -0.00559 0.04526 AFIX 43 H3 2 0.867444 0.042137 0.788859 11.00000 -1.20000 AFIX 0 C2 1 0.720264 0.063693 0.623685 11.00000 0.12408 0.14696 = 0.05710 0.00066 -0.01111 0.01682 AFIX 43 H2 2 0.861545 0.077271 0.632182 11.00000 -1.20000 AFIX 0 C1 1 0.502434 0.065486 0.516174 11.00000 0.09097 0.11447 = 0.04373 -0.00568 0.00237 0.02029 N2 3 0.241982 0.032026 0.013018 11.00000 0.02890 0.03910 = 0.06889 -0.00775 0.01270 -0.00206 AFIX 93 H2A 2 0.231260 0.013217 -0.010736 11.00000 -1.20000 H2B 2 0.381728 0.042516 0.012198 11.00000 -1.20000 AFIX 0 N1 3 0.066758 0.076132 0.079824 11.00000 0.02804 0.04073 = 0.04886 -0.00050 0.00467 -0.00185 O2 4 -0.163882 0.031667 0.055223 11.00000 0.03064 0.04605 = 0.07894 -0.01432 0.01509 -0.00421 O1 4 0.325359 0.087965 0.088559 11.00000 0.03044 0.04574 = 0.04797 0.00984 0.00539 -0.00511 AFIX 147 H1 2 0.325015 0.097481 0.022745 11.00000 -1.50000 AFIX 0 S1 5 0.450690 0.090045 0.387725 11.00000 0.08902 0.13453 = 0.04725 0.00654 -0.01519 -0.04799 C12 1 1.141136 0.249078 0.243939 11.00000 0.04282 0.04078 = 0.02969 -0.00007 0.00900 0.00843 C13 1 0.932942 0.225664 0.247360 11.00000 0.04065 0.03639 = 0.02728 0.00150 0.00901 0.00764 C17 1 0.796956 0.211590 0.133925 11.00000 0.05907 0.04492 = 0.02401 -0.00296 0.00846 0.00138 AFIX 43 H17 2 0.836503 0.216416 0.056465 11.00000 -1.20000 AFIX 0 C16 1 0.602642 0.190382 0.137354 11.00000 0.05754 0.04930 = 0.03520 -0.00413 0.00736 -0.00003 AFIX 43 H16 2 0.507576 0.180949 0.062074 11.00000 -1.20000 AFIX 0 C15 1 0.551285 0.183370 0.253022 11.00000 0.06244 0.03731 = 0.04320 -0.00187 0.01365 -0.00754 AFIX 43 H15 2 0.419612 0.169019 0.253945 11.00000 -1.20000 AFIX 0 C14 1 0.864702 0.217029 0.359438 11.00000 0.05746 0.05185 = 0.02798 -0.00670 0.00820 -0.00391 AFIX 43 H14 2 0.953103 0.226459 0.435973 11.00000 -1.20000 AFIX 0 N3 3 1.257741 0.263411 0.352436 11.00000 0.05769 0.05630 = 0.03142 -0.00215 0.01158 -0.00900 AFIX 93 H3A 2 1.380375 0.276683 0.353244 11.00000 -1.20000 H3B 2 1.210709 0.259433 0.421972 11.00000 -1.20000 AFIX 0 N4 3 0.680031 0.196025 0.364392 11.00000 0.06507 0.05484 = 0.03755 -0.00230 0.01779 -0.00555 O3 4 1.203606 0.254205 0.141689 11.00000 0.05741 0.05823 = 0.03180 0.00080 0.01304 -0.00512 C18 1 0.720205 0.185885 0.742133 11.00000 0.04875 0.05274 = 0.03316 0.00265 0.00898 -0.00336 C19 1 0.925062 0.161769 0.744257 11.00000 0.05081 0.04768 = 0.03878 0.00637 0.01144 0.00042 C23 1 1.016266 0.153058 0.639643 11.00000 0.09034 0.07895 = 0.04833 0.02339 0.02584 0.02913 AFIX 43 H23 2 0.950533 0.162533 0.560415 11.00000 -1.20000 AFIX 0 C22 1 1.205652 0.130214 0.652482 11.00000 0.11013 0.08450 = 0.07878 0.02299 0.05544 0.04567 AFIX 43 H22 2 1.267324 0.123827 0.582618 11.00000 -1.20000 AFIX 0 C21 1 1.298940 0.117360 0.771582 11.00000 0.07263 0.06719 = 0.10287 0.02658 0.02706 0.02179 AFIX 43 H21 2 1.428343 0.102244 0.780747 11.00000 -1.20000 AFIX 0 C20 1 1.034752 0.146947 0.858864 11.00000 0.06155 0.06127 = 0.04715 0.01291 0.00564 -0.00266 AFIX 43 H20 2 0.976900 0.152702 0.930652 11.00000 -1.20000 AFIX 0 N5 3 0.609640 0.199686 0.630418 11.00000 0.05738 0.05888 = 0.03353 -0.00192 0.01107 0.00987 AFIX 7 H5A 2 0.587611 0.186707 0.568406 11.00000 -1.20000 H5B 2 0.457515 0.207010 0.633458 11.00000 -1.20000 AFIX 0 N6 3 1.217929 0.124945 0.873926 11.00000 0.06623 0.05869 = 0.06697 0.02322 0.00718 0.00212 O4 4 0.663135 0.192797 0.843392 11.00000 0.07818 0.07698 = 0.02723 0.00412 0.01390 0.01732 HKLF 4 1 1 0 0 0 -1 0 -1 0 -1 REM g170904a in Pn #7 New: P21/c REM R1 = 0.0882 for 2415 Fo > 4sig(Fo) and 0.1654 for all 4806 data REM 311 parameters refined using 65 restraints END WGHT 0.0940 1.9130 REM Highest difference peak 0.512, deepest hole -0.697, 1-sigma level 0.064 Q1 1 0.1634 0.0417 0.3362 11.00000 0.05 0.51 Q2 1 0.3583 0.0118 0.5409 11.00000 0.05 0.47 Q3 1 0.3279 0.1020 0.3860 11.00000 0.05 0.46 Q4 1 0.6453 0.0803 0.6350 11.00000 0.05 0.42 Q5 1 0.6478 0.0301 0.7279 11.00000 0.05 0.42 Q6 1 0.3473 0.0306 0.6638 11.00000 0.05 0.36 Q7 1 0.0818 0.0550 0.4401 11.00000 0.05 0.30 Q8 1 0.6655 0.1976 0.5417 11.00000 0.05 0.28 Q9 1 0.4454 0.0074 0.6815 11.00000 0.05 0.28 Q10 1 0.3700 0.0515 0.5425 11.00000 0.05 0.27 Q11 1 0.8491 0.0573 0.7041 11.00000 0.05 0.24 Q12 1 0.1525 0.0216 0.6181 11.00000 0.05 0.24 Q13 1 0.3765 0.1169 -0.0386 11.00000 0.05 0.23 Q14 1 0.4608 0.0798 0.4853 11.00000 0.05 0.22 Q15 1 0.8356 0.1720 0.8859 11.00000 0.05 0.21 Q16 1 0.8664 0.0701 0.5971 11.00000 0.05 0.21 Q17 1 0.3434 0.1073 0.1929 11.00000 0.05 0.20 Q18 1 -0.4043 0.0760 0.2650 11.00000 0.05 0.20 Q19 1 1.0714 0.2596 0.0768 11.00000 0.05 0.20 Q20 1 1.5047 0.2775 0.1404 11.00000 0.05 0.20 REM The information below was added by Olex2. REM REM R1 = 0.0882 for 2415 Fo > 4sig(Fo) and 0.1654 for all 17057 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.51, deepest hole -0.70 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.1654 REM R1_gt = 0.0882 REM wR_ref = 0.2634 REM GOOF = 1.056 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 17057 REM Reflections_gt = 2415 REM Parameters = n/a REM Hole = -0.70 REM Peak = 0.51 REM Flack = n/a ; _cod_data_source_file c7ce02150j2.cif _cod_data_source_block g170904a _cod_database_code 7229953 _chemical_oxdiff_formula 'C H O N S' _reflns_odcompleteness_completeness 98.25 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 28.22 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2. Rigid bond restraints C8, C7, C6, C5, C4, C3, C2, C1 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.002 3. Uiso/Uaniso restraints and constraints C8 \\sim C7 \\sim C6 \\sim C5 \\sim C4 \\sim C3 \\sim C2 \\sim C1: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.004 4.a Rotating group: N5(H5A,H5B) 4.b Ternary CH refined with riding coordinates: C9(H9) 4.c Aromatic/amide H refined with riding coordinates: C7(H7), C5(H5), C4(H4), C3(H3), C2(H2), C17(H17), C16(H16), C15(H15), C14(H14), C23(H23), C22(H22), C21(H21), C20(H20) 4.d X=CH2 refined with riding coordinates: N2(H2A,H2B), N3(H3A,H3B) 4.e Idealised Me refined as rotating group: C10(H10A,H10B,H10C) 4.f Idealised tetrahedral OH refined as rotating group: O1(H1) ; _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -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_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp C11 C 0.0435(8) 0.04483(10) 0.0508(4) 0.0396(11) Uani 1 d . . C9 C -0.0290(9) 0.08545(10) 0.1921(5) 0.0419(12) Uani 1 d . . H9 H -0.2039 0.0759 0.1827 0.050 Uiso 1 calc R . C10 C -0.0721(10) 0.11987(11) 0.1895(6) 0.0578(15) Uani 1 d . . H10A H -0.1316 0.1259 0.2636 0.087 Uiso 1 calc GR . H10B H -0.2044 0.1254 0.1127 0.087 Uiso 1 calc GR . H10C H 0.0924 0.1300 0.1906 0.087 Uiso 1 calc GR . C8 C 0.1474(9) 0.07417(12) 0.3161(5) 0.0502(12) Uani 1 d . U C7 C 0.0983(14) 0.05108(15) 0.3869(7) 0.0892(17) Uani 1 d . U H7 H -0.0574 0.0396 0.3638 0.107 Uiso 1 calc R . C6 C 0.3030(16) 0.04527(19) 0.5012(7) 0.0993(17) Uani 1 d . U C5 C 0.3173(19) 0.0230(2) 0.5999(8) 0.131(2) Uani 1 d . U H5 H 0.1793 0.0092 0.5959 0.157 Uiso 1 calc R . C4 C 0.541(2) 0.0226(2) 0.7009(8) 0.127(2) Uani 1 d . U H4 H 0.5581 0.0072 0.7620 0.152 Uiso 1 calc R . C3 C 0.727(2) 0.0424(2) 0.7152(8) 0.122(2) Uani 1 d . U H3 H 0.8674 0.0421 0.7889 0.147 Uiso 1 calc R . C2 C 0.7203(17) 0.0637(2) 0.6237(7) 0.116(2) Uani 1 d . U H2 H 0.8615 0.0773 0.6322 0.139 Uiso 1 calc R . C1 C 0.5024(15) 0.06549(18) 0.5162(6) 0.0857(16) Uani 1 d . U N2 N 0.2420(7) 0.03203(8) 0.0130(4) 0.0456(11) Uani 1 d . . H2A H 0.2313 0.0132 -0.0107 0.055 Uiso 1 calc R . H2B H 0.3817 0.0425 0.0122 0.055 Uiso 1 calc R . N1 N 0.0668(7) 0.07613(8) 0.0798(4) 0.0401(10) Uani 1 d . . O2 O -0.1639(6) 0.03167(7) 0.0552(4) 0.0517(10) Uani 1 d . . O1 O 0.3254(5) 0.08797(7) 0.0886(3) 0.0422(8) Uani 1 d . . H1 H 0.3250 0.0975 0.0227 0.063 Uiso 1 calc GR . S1 S 0.4507(4) 0.09004(5) 0.38772(15) 0.0961(8) Uani 1 d . . C12 C 1.1411(9) 0.24908(10) 0.2439(4) 0.0378(11) Uani 1 d . . C13 C 0.9329(8) 0.22566(9) 0.2474(4) 0.0347(10) Uani 1 d . . C17 C 0.7970(9) 0.21159(10) 0.1339(4) 0.0430(12) Uani 1 d . . H17 H 0.8365 0.2164 0.0565 0.052 Uiso 1 calc R . C16 C 0.6026(10) 0.19038(11) 0.1374(5) 0.0481(13) Uani 1 d . . H16 H 0.5076 0.1809 0.0621 0.058 Uiso 1 calc R . C15 C 0.5513(10) 0.18337(11) 0.2530(5) 0.0476(12) Uani 1 d . . H15 H 0.4196 0.1690 0.2539 0.057 Uiso 1 calc R . C14 C 0.8647(10) 0.21703(11) 0.3594(4) 0.0462(12) Uani 1 d . . H14 H 0.9531 0.2265 0.4360 0.055 Uiso 1 calc R . N3 N 1.2577(8) 0.26341(9) 0.3524(4) 0.0484(11) Uani 1 d . . H3A H 1.3804 0.2767 0.3532 0.058 Uiso 1 calc R . H3B H 1.2107 0.2594 0.4220 0.058 Uiso 1 calc R . N4 N 0.6800(8) 0.19602(10) 0.3644(4) 0.0516(11) Uani 1 d . . O3 O 1.2036(7) 0.25421(7) 0.1417(3) 0.0488(9) Uani 1 d . . C18 C 0.7202(9) 0.18588(11) 0.7421(5) 0.0451(12) Uani 1 d . . C19 C 0.9251(9) 0.16177(11) 0.7443(4) 0.0457(12) Uani 1 d . . C23 C 1.0163(12) 0.15306(14) 0.6396(6) 0.0711(17) Uani 1 d . . H23 H 0.9505 0.1625 0.5604 0.085 Uiso 1 calc R . C22 C 1.2057(14) 0.13021(15) 0.6525(7) 0.085(2) Uani 1 d . . H22 H 1.2673 0.1238 0.5826 0.103 Uiso 1 calc R . C21 C 1.2989(13) 0.11736(15) 0.7716(8) 0.080(2) Uani 1 d . . H21 H 1.4283 0.1022 0.7807 0.096 Uiso 1 calc R . C20 C 1.0348(11) 0.14695(13) 0.8589(5) 0.0581(15) Uani 1 d . . H20 H 0.9769 0.1527 0.9307 0.070 Uiso 1 calc R . N5 N 0.6096(8) 0.19969(10) 0.6304(4) 0.0500(11) Uani 1 d . . H5A H 0.5876 0.1867 0.5684 0.060 Uiso 1 d GR . H5B H 0.4575 0.2070 0.6335 0.060 Uiso 1 d GR . N6 N 1.2179(10) 0.12494(11) 0.8739(5) 0.0657(14) Uani 1 d . . O4 O 0.6631(7) 0.19280(9) 0.8434(3) 0.0607(11) Uani 1 d . . 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 C11 0.030(2) 0.040(3) 0.046(3) 0.001(2) 0.004(2) 0.0036(19) C9 0.034(2) 0.036(3) 0.054(3) -0.001(2) 0.008(2) 0.0013(18) C10 0.046(3) 0.042(3) 0.082(4) -0.006(3) 0.011(3) 0.003(2) C8 0.043(2) 0.050(3) 0.058(3) 0.004(2) 0.014(2) 0.011(2) C7 0.082(3) 0.080(3) 0.092(3) 0.035(3) -0.002(3) 0.003(3) C6 0.103(3) 0.101(3) 0.081(3) 0.033(2) 0.000(3) 0.022(3) C5 0.140(4) 0.130(4) 0.104(4) 0.054(3) -0.005(3) 0.025(3) C4 0.146(5) 0.140(5) 0.080(3) 0.038(3) 0.002(3) 0.050(3) C3 0.139(4) 0.152(5) 0.058(3) 0.007(3) -0.006(3) 0.045(3) C2 0.124(4) 0.147(4) 0.057(3) 0.001(3) -0.011(3) 0.017(3) C1 0.091(3) 0.114(4) 0.044(2) -0.006(2) 0.002(2) 0.020(3) N2 0.0289(19) 0.039(2) 0.069(3) -0.008(2) 0.0127(19) -0.0021(16) N1 0.0280(18) 0.041(2) 0.049(2) -0.0005(18) 0.0047(17) -0.0019(16) O2 0.0306(16) 0.0460(19) 0.079(3) -0.0143(17) 0.0151(16) -0.0042(14) O1 0.0304(15) 0.0457(19) 0.048(2) 0.0098(15) 0.0054(14) -0.0051(13) S1 0.0890(13) 0.1345(17) 0.0473(10) 0.0065(9) -0.0152(9) -0.0480(12) C12 0.043(2) 0.041(3) 0.030(2) 0.000(2) 0.009(2) 0.0084(19) C13 0.041(2) 0.036(2) 0.027(2) 0.0015(19) 0.0090(19) 0.0076(18) C17 0.059(3) 0.045(3) 0.024(2) -0.003(2) 0.008(2) 0.001(2) C16 0.058(3) 0.049(3) 0.035(3) -0.004(2) 0.007(2) 0.000(2) C15 0.062(3) 0.037(3) 0.043(3) -0.002(2) 0.014(2) -0.008(2) C14 0.057(3) 0.052(3) 0.028(2) -0.007(2) 0.008(2) -0.004(2) N3 0.058(3) 0.056(3) 0.031(2) -0.0022(19) 0.0116(19) -0.009(2) N4 0.065(3) 0.055(3) 0.038(2) -0.002(2) 0.018(2) -0.006(2) O3 0.057(2) 0.058(2) 0.0318(18) 0.0008(15) 0.0130(16) -0.0051(16) C18 0.049(3) 0.053(3) 0.033(3) 0.003(2) 0.009(2) -0.003(2) C19 0.051(3) 0.048(3) 0.039(3) 0.006(2) 0.011(2) 0.000(2) C23 0.090(4) 0.079(4) 0.048(3) 0.023(3) 0.026(3) 0.029(3) C22 0.110(5) 0.084(5) 0.079(5) 0.023(4) 0.055(4) 0.046(4) C21 0.073(4) 0.067(4) 0.103(6) 0.027(4) 0.027(4) 0.022(3) C20 0.062(3) 0.061(3) 0.047(3) 0.013(3) 0.006(3) -0.003(3) N5 0.057(3) 0.059(3) 0.034(2) -0.0019(19) 0.0111(19) 0.010(2) N6 0.066(3) 0.059(3) 0.067(3) 0.023(3) 0.007(3) 0.002(2) O4 0.078(3) 0.077(3) 0.0272(18) 0.0041(17) 0.0139(18) 0.017(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' S S 0.1246 0.1234 '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 N2 C11 N1 116.9(4) O2 C11 N2 124.6(4) O2 C11 N1 118.4(4) C10 C9 H9 107.0 C8 C9 H9 107.0 C8 C9 C10 113.4(4) N1 C9 H9 107.0 N1 C9 C10 109.7(4) N1 C9 C8 112.3(4) C9 C10 H10A 109.5 C9 C10 H10B 109.5 C9 C10 H10C 109.5 H10A C10 H10B 109.5 H10A C10 H10C 109.5 H10B C10 H10C 109.5 C9 C8 S1 123.4(4) C7 C8 C9 126.7(5) C7 C8 S1 109.9(4) C8 C7 H7 122.6 C8 C7 C6 114.8(7) C6 C7 H7 122.6 C5 C6 C7 130.3(8) C1 C6 C7 111.6(7) C1 C6 C5 118.0(7) C6 C5 H5 121.0 C4 C5 C6 118.0(9) C4 C5 H5 121.0 C5 C4 H4 118.4 C3 C4 C5 123.2(9) C3 C4 H4 118.4 C4 C3 H3 119.9 C4 C3 C2 120.2(8) C2 C3 H3 119.9 C3 C2 H2 119.8 C3 C2 C1 120.4(9) C1 C2 H2 119.8 C6 C1 C2 120.0(7) C6 C1 S1 111.1(5) C2 C1 S1 128.9(7) C11 N2 H2A 120.0 C11 N2 H2B 120.0 H2A N2 H2B 120.0 C11 N1 C9 115.1(4) C11 N1 O1 113.5(3) O1 N1 C9 110.7(3) N1 O1 H1 109.5 C8 S1 C1 92.6(3) N3 C12 C13 118.3(4) O3 C12 C13 119.8(4) O3 C12 N3 121.9(4) C17 C13 C12 119.5(4) C17 C13 C14 117.0(4) C14 C13 C12 123.5(4) C13 C17 H17 120.4 C16 C17 C13 119.2(4) C16 C17 H17 120.4 C17 C16 H16 120.4 C15 C16 C17 119.2(4) C15 C16 H16 120.4 C16 C15 H15 118.3 N4 C15 C16 123.5(5) N4 C15 H15 118.3 C13 C14 H14 117.9 N4 C14 C13 124.3(4) N4 C14 H14 117.9 C12 N3 H3A 120.0 C12 N3 H3B 120.0 H3A N3 H3B 120.0 C15 N4 C14 116.8(4) N5 C18 C19 118.4(4) O4 C18 C19 119.2(4) O4 C18 N5 122.4(5) C23 C19 C18 124.9(4) C23 C19 C20 116.6(5) C20 C19 C18 118.5(5) C19 C23 H23 120.0 C19 C23 C22 120.0(5) C22 C23 H23 120.0 C23 C22 H22 121.2 C21 C22 C23 117.7(6) C21 C22 H22 121.2 C22 C21 H21 117.8 N6 C21 C22 124.4(6) N6 C21 H21 117.8 C19 C20 H20 117.7 N6 C20 C19 124.6(6) N6 C20 H20 117.7 C18 N5 H5A 109.8 C18 N5 H5B 108.9 H5A N5 H5B 109.4 C21 N6 C20 116.7(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C11 N2 1.323(6) C11 N1 1.404(6) C11 O2 1.231(5) C9 H9 0.9800 C9 C10 1.523(6) C9 C8 1.496(7) C9 N1 1.473(6) C10 H10A 0.9600 C10 H10B 0.9600 C10 H10C 0.9600 C8 C7 1.328(8) C8 S1 1.713(5) C7 H7 0.9300 C7 C6 1.427(9) C6 C5 1.427(11) C6 C1 1.340(10) C5 H5 0.9300 C5 C4 1.373(11) C4 H4 0.9300 C4 C3 1.275(13) C3 H3 0.9300 C3 C2 1.348(12) C2 H2 0.9300 C2 C1 1.398(9) C1 S1 1.716(7) N2 H2A 0.8600 N2 H2B 0.8600 N1 O1 1.418(4) O1 H1 0.8200 C12 C13 1.496(6) C12 N3 1.326(5) C12 O3 1.241(5) C13 C17 1.387(6) C13 C14 1.390(6) C17 H17 0.9300 C17 C16 1.378(7) C16 H16 0.9300 C16 C15 1.369(7) C15 H15 0.9300 C15 N4 1.333(6) C14 H14 0.9300 C14 N4 1.339(6) N3 H3A 0.8600 N3 H3B 0.8600 C18 C19 1.494(7) C18 N5 1.336(6) C18 O4 1.235(6) C19 C23 1.379(7) C19 C20 1.380(7) C23 H23 0.9300 C23 C22 1.384(8) C22 H22 0.9300 C22 C21 1.368(9) C21 H21 0.9300 C21 N6 1.315(8) C20 H20 0.9300 C20 N6 1.334(7) N5 H5A 0.8608 N5 H5B 0.8599 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 H2A O2 0.86 2.03 2.887(5) 172.2 3 O1 H1 N6 0.82 1.96 2.756(5) 161.9 1_454 N3 H3A O4 0.86 2.01 2.866(5) 176.5 4_665 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 C9 C8 C7 C6 179.9(6) C9 C8 S1 C1 178.5(5) C10 C9 C8 C7 130.5(7) C10 C9 C8 S1 -49.5(6) C10 C9 N1 C11 -163.0(4) C10 C9 N1 O1 66.7(4) C8 C9 N1 C11 69.9(5) C8 C9 N1 O1 -60.4(5) C8 C7 C6 C5 178.9(9) C8 C7 C6 C1 2.3(11) C7 C8 S1 C1 -1.5(6) C7 C6 C5 C4 -179.7(9) C7 C6 C1 C2 179.2(7) C7 C6 C1 S1 -3.4(9) C6 C5 C4 C3 5.0(16) C6 C1 S1 C8 2.9(6) C5 C6 C1 C2 2.2(13) C5 C6 C1 S1 179.6(7) C5 C4 C3 C2 -5.2(17) C4 C3 C2 C1 3.8(15) C3 C2 C1 C6 -2.4(13) C3 C2 C1 S1 -179.2(7) C2 C1 S1 C8 179.9(8) C1 C6 C5 C4 -3.3(14) N2 C11 N1 C9 -140.9(4) N2 C11 N1 O1 -11.9(5) N1 C9 C8 C7 -104.3(7) N1 C9 C8 S1 75.7(5) O2 C11 N1 C9 43.1(5) O2 C11 N1 O1 172.1(4) S1 C8 C7 C6 -0.1(8) C12 C13 C17 C16 -179.0(4) C12 C13 C14 N4 -179.6(4) C13 C17 C16 C15 -1.0(7) C13 C14 N4 C15 -1.6(7) C17 C13 C14 N4 0.7(7) C17 C16 C15 N4 0.0(8) C16 C15 N4 C14 1.3(7) C14 C13 C17 C16 0.7(6) N3 C12 C13 C17 176.3(4) N3 C12 C13 C14 -3.4(6) O3 C12 C13 C17 -5.0(6) O3 C12 C13 C14 175.4(4) C18 C19 C23 C22 -179.5(6) C18 C19 C20 N6 179.7(5) C19 C23 C22 C21 -1.0(10) C19 C20 N6 C21 0.7(8) C23 C19 C20 N6 -0.7(8) C23 C22 C21 N6 1.0(11) C22 C21 N6 C20 -0.8(10) C20 C19 C23 C22 0.9(9) N5 C18 C19 C23 2.0(8) N5 C18 C19 C20 -178.4(4) O4 C18 C19 C23 -176.5(5) O4 C18 C19 C20 3.1(7)