#------------------------------------------------------------------------------ #$Date: 2019-11-08 04:10:20 +0200 (Fri, 08 Nov 2019) $ #$Revision: 225313 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/71/7157147.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_7157147 loop_ _publ_author_name 'Luo, Shao-Xiong' 'Liu, Yanzhou' 'Lambrecht, Michael J.' 'Ortwine, Daniel F.' 'DiPasquale, Antonio G.' 'Liang, Jun' 'Wang, Xiaojing' 'Zbieg, Jason R.' 'Li, Jun' _publ_section_title ; cis-Selective synthesis of 1,3-disubstituted tetrahydro-\b-carbolines from N-sulfonyl N,S-acetals. ; _journal_issue 43 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 9510 _journal_paper_doi 10.1039/c9ob01796h _journal_volume 17 _journal_year 2019 _chemical_absolute_configuration ad _chemical_formula_sum 'C25 H24 N2 O2 S' _chemical_formula_weight 416.52 _chemical_name_systematic 28 _space_group.centring_type primitive _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-03-04 deposited with the CCDC. 2019-10-09 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.0518(4) _cell_length_b 12.1315(5) _cell_length_c 18.9731(8) _cell_measurement_reflns_used 8729 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 25.38 _cell_measurement_theta_min 2.49 _cell_volume 2083.47(15) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics ORTEP-32 _computing_publication_material WinGX _computing_structure_refinement SHELXL-2014 _computing_structure_solution SHELXT-2014 _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 8.366 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-I CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0602 _diffrn_reflns_av_unetI/netI 0.0430 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_refln_scan_rate 20 _diffrn_refln_scan_width 1.0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 26438 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 25.377 _diffrn_reflns_theta_min 1.993 _diffrn_source 'fine focus sealed tube' _exptl_absorpt_coefficient_mu 0.180 _exptl_absorpt_correction_T_max 0.928 _exptl_absorpt_correction_T_min 0.851 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.328 _exptl_crystal_description prism _exptl_crystal_F_000 880 _exptl_crystal_size_max 0.070 _exptl_crystal_size_mid 0.030 _exptl_crystal_size_min 0.030 _refine_diff_density_max 0.255 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.050 _refine_ls_abs_structure_details ; Flack x determined using 1342 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.04(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 273 _refine_ls_number_reflns 3817 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.081 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0403 _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^)+(0.0396P)^2^+0.7032P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0889 _refine_ls_wR_factor_ref 0.0922 _reflns_Friedel_coverage 0.744 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.998 _reflns_number_gt 3452 _reflns_number_total 3817 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ob01796h2.cif _cod_data_source_block 28 _cod_depositor_comments 'Adding full bibliography for 7157147--7157148.cif.' _cod_database_code 7157147 _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_estimated_absorpt_t_min 0.987 _shelx_estimated_absorpt_t_max 0.995 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL gene707_0m_a.res in P2(1)2(1)2(1) CELL 0.71073 9.0518 12.1315 18.9731 90.000 90.000 90.000 ZERR 4.00 0.0004 0.0005 0.0008 0.000 0.000 0.000 LATT -1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM - X, 1/2 + Y, 1/2 - Z SYMM 1/2 + X, 1/2 - Y, - Z SFAC C H N O S UNIT 100 96 8 8 4 MERG 2 FMAP 2 PLAN 20 SIZE 0.030 0.030 0.070 ACTA 50.00 BOND $H LIST 4 WPDB -2 L.S. 10 TEMP -173.00 WGHT 0.039600 0.703200 FVAR 0.20941 C1 1 0.626647 0.451408 0.307388 11.00000 0.02047 0.01865 = 0.01674 0.00526 -0.00149 -0.00083 AFIX 13 H1 2 0.555829 0.462352 0.267545 11.00000 -1.20000 AFIX 0 C2 1 0.614120 0.552521 0.354641 11.00000 0.02128 0.01630 = 0.01921 0.00346 -0.00099 -0.00174 AFIX 23 H2A 2 0.662711 0.616323 0.331816 11.00000 -1.20000 H2B 2 0.508771 0.571047 0.362137 11.00000 -1.20000 AFIX 0 C3 1 0.686702 0.528905 0.424098 11.00000 0.01865 0.01590 = 0.01887 0.00092 0.00017 -0.00086 C4 1 0.754273 0.600431 0.474998 11.00000 0.01630 0.01903 = 0.01960 -0.00094 0.00128 0.00248 C5 1 0.773728 0.715450 0.480451 11.00000 0.02314 0.01639 = 0.02404 -0.00021 -0.00104 -0.00144 AFIX 43 H5 2 0.735275 0.763484 0.445419 11.00000 -1.20000 AFIX 0 C6 1 0.849671 0.756825 0.537638 11.00000 0.02366 0.01806 = 0.03170 -0.00584 0.00132 0.00033 AFIX 43 H6 2 0.865416 0.834068 0.540997 11.00000 -1.20000 AFIX 0 C7 1 0.904125 0.688122 0.590815 11.00000 0.01866 0.02292 = 0.02499 -0.00825 -0.00235 -0.00164 AFIX 43 H7 2 0.954714 0.719631 0.629785 11.00000 -1.20000 AFIX 0 C8 1 0.885517 0.574772 0.587615 11.00000 0.02158 0.02126 = 0.01921 -0.00162 0.00068 0.00146 AFIX 43 H8 2 0.921389 0.527736 0.623804 11.00000 -1.20000 AFIX 0 C9 1 0.811722 0.532901 0.528840 11.00000 0.01537 0.01801 = 0.01803 -0.00051 0.00453 -0.00128 C10 1 0.703245 0.424606 0.448566 11.00000 0.01750 0.01866 = 0.01594 -0.00068 0.00059 0.00129 C11 1 0.641052 0.321432 0.416736 11.00000 0.01943 0.01741 = 0.01262 0.00117 -0.00246 -0.00237 AFIX 13 H11 2 0.556975 0.297428 0.447288 11.00000 -1.20000 AFIX 0 C12 1 0.779179 0.436881 0.274859 11.00000 0.02217 0.02514 = 0.02205 0.00149 0.00221 -0.00153 AFIX 137 H12A 2 0.853884 0.436187 0.312242 11.00000 -1.50000 H12B 2 0.799095 0.498035 0.242475 11.00000 -1.50000 H12C 2 0.782733 0.367073 0.248922 11.00000 -1.50000 AFIX 0 C13 1 0.749638 0.225922 0.413231 11.00000 0.02039 0.01844 = 0.01229 0.00164 -0.00313 -0.00109 C14 1 0.899473 0.242634 0.399194 11.00000 0.02746 0.01756 = 0.01890 0.00041 -0.00465 -0.00174 AFIX 43 H14 2 0.935461 0.315306 0.391905 11.00000 -1.20000 AFIX 0 C15 1 0.996052 0.154233 0.395807 11.00000 0.02436 0.02907 = 0.02268 -0.00161 -0.00447 0.00282 AFIX 43 H15 2 1.097223 0.166475 0.385033 11.00000 -1.20000 AFIX 0 C16 1 0.945678 0.047607 0.408098 11.00000 0.03157 0.02365 = 0.02426 -0.00437 -0.00796 0.00734 AFIX 43 H16 2 1.012294 -0.012854 0.406529 11.00000 -1.20000 AFIX 0 C17 1 0.797692 0.030434 0.422627 11.00000 0.03527 0.01785 = 0.02128 -0.00145 -0.00874 -0.00130 AFIX 43 H17 2 0.762346 -0.042096 0.431115 11.00000 -1.20000 AFIX 0 C18 1 0.700666 0.119151 0.424823 11.00000 0.02291 0.02078 = 0.01982 0.00085 -0.00384 -0.00431 AFIX 43 H18 2 0.599084 0.106430 0.434427 11.00000 -1.20000 AFIX 0 C19 1 0.290453 0.407551 0.325478 11.00000 0.01710 0.01905 = 0.01930 -0.00122 -0.00356 -0.00553 C20 1 0.263352 0.469641 0.265550 11.00000 0.02137 0.02960 = 0.02014 -0.00054 -0.00148 -0.00088 AFIX 43 H20 2 0.303674 0.448000 0.221441 11.00000 -1.20000 AFIX 0 C21 1 0.176773 0.563720 0.270556 11.00000 0.02258 0.03083 = 0.02383 0.00659 -0.00203 -0.00061 AFIX 43 H21 2 0.160396 0.607398 0.229739 11.00000 -1.20000 AFIX 0 C22 1 0.113676 0.595143 0.334134 11.00000 0.01945 0.02506 = 0.02998 0.00061 -0.00109 -0.00381 C23 1 0.137983 0.528729 0.393004 11.00000 0.02424 0.02557 = 0.02596 -0.00461 0.00552 -0.00442 AFIX 43 H23 2 0.091846 0.547160 0.436405 11.00000 -1.20000 AFIX 0 C24 1 0.227401 0.437000 0.389616 11.00000 0.02186 0.02268 = 0.02021 0.00037 -0.00071 -0.00484 AFIX 43 H24 2 0.245806 0.394304 0.430661 11.00000 -1.20000 AFIX 0 C25 1 0.021792 0.698601 0.338688 11.00000 0.02900 0.02891 = 0.04208 0.00589 0.00689 0.00328 AFIX 137 H25A 2 -0.077166 0.680163 0.356010 11.00000 -1.50000 H25B 2 0.014024 0.732160 0.291851 11.00000 -1.50000 H25C 2 0.068811 0.750708 0.371164 11.00000 -1.50000 AFIX 0 N1 3 0.577745 0.350305 0.346102 11.00000 0.02046 0.01753 = 0.01616 0.00249 -0.00157 -0.00152 N2 3 0.780353 0.424875 0.511244 11.00000 0.02017 0.01590 = 0.01659 0.00209 -0.00292 -0.00071 AFIX 43 H2 2 0.805323 0.366264 0.535838 11.00000 -1.20000 AFIX 0 O1 4 0.380052 0.216610 0.373081 11.00000 0.02558 0.02180 = 0.02335 0.00384 -0.00162 -0.00584 O2 4 0.430350 0.266791 0.249137 11.00000 0.02864 0.02446 = 0.01807 -0.00511 -0.00088 -0.00371 S1 5 0.419656 0.298698 0.321677 11.00000 0.02069 0.01847 = 0.01651 -0.00066 -0.00123 -0.00324 HKLF 4 REM gene707_0m_a.res in P2(1)2(1)2(1) REM R1 = 0.0403 for 3452 Fo > 4sig(Fo) and 0.0472 for all 3817 data REM 273 parameters refined using 0 restraints END WGHT 0.0391 0.7224 REM Highest difference peak 0.255, deepest hole -0.290, 1-sigma level 0.050 Q1 1 0.3555 0.3658 0.3287 11.00000 0.05 0.25 Q2 1 0.6022 0.4015 0.3273 11.00000 0.05 0.23 Q3 1 0.6947 0.2689 0.4112 11.00000 0.05 0.20 Q4 1 0.4905 0.3522 0.3274 11.00000 0.05 0.20 Q5 1 0.9529 0.6388 0.5740 11.00000 0.05 0.20 Q6 1 0.8646 0.7339 0.4914 11.00000 0.05 0.19 Q7 1 0.6710 0.5398 0.3949 11.00000 0.05 0.19 Q8 1 0.6617 0.4806 0.4332 11.00000 0.05 0.19 Q9 1 0.4600 0.3258 0.2621 11.00000 0.05 0.18 Q10 1 0.4309 0.1752 0.3854 11.00000 0.05 0.18 Q11 1 0.6056 0.3365 0.3766 11.00000 0.05 0.18 Q12 1 0.7414 0.5659 0.4322 11.00000 0.05 0.17 Q13 1 0.3380 0.2126 0.3931 11.00000 0.05 0.17 Q14 1 0.8077 0.5586 0.5678 11.00000 0.05 0.17 Q15 1 -0.0756 0.6637 0.3151 11.00000 0.05 0.17 Q16 1 0.5876 0.3130 0.4377 11.00000 0.05 0.17 Q17 1 0.7062 0.5974 0.3277 11.00000 0.05 0.17 Q18 1 0.2855 0.4179 0.3439 11.00000 0.05 0.17 Q19 1 0.4285 0.2552 0.3834 11.00000 0.05 0.17 Q20 1 0.2986 0.4470 0.3050 11.00000 0.05 0.16 ; _shelx_res_checksum 59813 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -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 C1 C 0.6266(4) 0.4514(3) 0.30739(17) 0.0186(7) Uani 1 1 d . . H1 H 0.5558 0.4624 0.2675 0.022 Uiso 1 1 calc R U C2 C 0.6141(4) 0.5525(2) 0.35464(17) 0.0189(7) Uani 1 1 d . . H2A H 0.6627 0.6163 0.3318 0.023 Uiso 1 1 calc R U H2B H 0.5088 0.5710 0.3621 0.023 Uiso 1 1 calc R U C3 C 0.6867(4) 0.5289(3) 0.42410(17) 0.0178(7) Uani 1 1 d . . C4 C 0.7543(4) 0.6004(3) 0.47500(17) 0.0183(7) Uani 1 1 d . . C5 C 0.7737(4) 0.7154(3) 0.48045(17) 0.0212(8) Uani 1 1 d . . H5 H 0.7353 0.7635 0.4454 0.025 Uiso 1 1 calc R U C6 C 0.8497(4) 0.7568(3) 0.53764(19) 0.0245(8) Uani 1 1 d . . H6 H 0.8654 0.8341 0.5410 0.029 Uiso 1 1 calc R U C7 C 0.9041(4) 0.6881(3) 0.59081(17) 0.0222(7) Uani 1 1 d . . H7 H 0.9547 0.7196 0.6298 0.027 Uiso 1 1 calc R U C8 C 0.8855(4) 0.5748(3) 0.58762(17) 0.0207(8) Uani 1 1 d . . H8 H 0.9214 0.5277 0.6238 0.025 Uiso 1 1 calc R U C9 C 0.8117(4) 0.5329(3) 0.52884(17) 0.0171(7) Uani 1 1 d . . C10 C 0.7032(4) 0.4246(3) 0.44857(17) 0.0174(7) Uani 1 1 d . . C11 C 0.6411(4) 0.3214(2) 0.41674(16) 0.0165(7) Uani 1 1 d . . H11 H 0.5570 0.2974 0.4473 0.020 Uiso 1 1 calc R U C12 C 0.7792(4) 0.4369(3) 0.27486(18) 0.0231(8) Uani 1 1 d . . H12A H 0.8539 0.4362 0.3122 0.035 Uiso 1 1 calc R U H12B H 0.7991 0.4980 0.2425 0.035 Uiso 1 1 calc R U H12C H 0.7827 0.3671 0.2489 0.035 Uiso 1 1 calc R U C13 C 0.7496(4) 0.2259(3) 0.41323(16) 0.0170(7) Uani 1 1 d . . C14 C 0.8995(4) 0.2426(3) 0.39919(16) 0.0213(8) Uani 1 1 d . . H14 H 0.9355 0.3153 0.3919 0.026 Uiso 1 1 calc R U C15 C 0.9961(4) 0.1542(3) 0.39581(18) 0.0254(8) Uani 1 1 d . . H15 H 1.0972 0.1665 0.3850 0.030 Uiso 1 1 calc R U C16 C 0.9457(4) 0.0476(3) 0.40810(18) 0.0265(9) Uani 1 1 d . . H16 H 1.0123 -0.0129 0.4065 0.032 Uiso 1 1 calc R U C17 C 0.7977(4) 0.0304(3) 0.42263(18) 0.0248(8) Uani 1 1 d . . H17 H 0.7623 -0.0421 0.4311 0.030 Uiso 1 1 calc R U C18 C 0.7007(4) 0.1192(3) 0.42482(17) 0.0212(8) Uani 1 1 d . . H18 H 0.5991 0.1064 0.4344 0.025 Uiso 1 1 calc R U C19 C 0.2905(4) 0.4076(3) 0.32548(18) 0.0185(7) Uani 1 1 d . . C20 C 0.2634(4) 0.4696(3) 0.26555(18) 0.0237(8) Uani 1 1 d . . H20 H 0.3037 0.4480 0.2214 0.028 Uiso 1 1 calc R U C21 C 0.1768(4) 0.5637(3) 0.27056(19) 0.0257(8) Uani 1 1 d . . H21 H 0.1604 0.6074 0.2297 0.031 Uiso 1 1 calc R U C22 C 0.1137(4) 0.5951(3) 0.33413(18) 0.0248(8) Uani 1 1 d . . C23 C 0.1380(4) 0.5287(3) 0.39300(19) 0.0253(8) Uani 1 1 d . . H23 H 0.0918 0.5472 0.4364 0.030 Uiso 1 1 calc R U C24 C 0.2274(4) 0.4370(3) 0.38962(18) 0.0216(8) Uani 1 1 d . . H24 H 0.2458 0.3943 0.4307 0.026 Uiso 1 1 calc R U C25 C 0.0218(4) 0.6986(3) 0.3387(2) 0.0333(9) Uani 1 1 d . . H25A H -0.0772 0.6802 0.3560 0.050 Uiso 1 1 calc R U H25B H 0.0140 0.7322 0.2919 0.050 Uiso 1 1 calc R U H25C H 0.0688 0.7507 0.3712 0.050 Uiso 1 1 calc R U N1 N 0.5777(3) 0.3503(2) 0.34610(13) 0.0180(6) Uani 1 1 d . . N2 N 0.7804(3) 0.4249(2) 0.51124(14) 0.0176(6) Uani 1 1 d . . H2 H 0.8053 0.3663 0.5358 0.021 Uiso 1 1 calc R U O1 O 0.3801(3) 0.21661(18) 0.37308(12) 0.0236(6) Uani 1 1 d . . O2 O 0.4304(3) 0.26679(18) 0.24914(12) 0.0237(6) Uani 1 1 d . . S1 S 0.41966(9) 0.29870(6) 0.32168(4) 0.0186(2) Uani 1 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 C1 0.0205(18) 0.0187(16) 0.0167(17) 0.0053(13) -0.0015(13) -0.0008(14) C2 0.021(2) 0.0163(16) 0.0192(16) 0.0035(14) -0.0010(14) -0.0017(14) C3 0.0187(18) 0.0159(15) 0.0189(17) 0.0009(14) 0.0002(15) -0.0009(14) C4 0.0163(18) 0.0190(17) 0.0196(17) -0.0009(14) 0.0013(14) 0.0025(14) C5 0.0231(19) 0.0164(16) 0.0240(18) -0.0002(15) -0.0010(15) -0.0014(15) C6 0.0237(19) 0.0181(17) 0.032(2) -0.0058(15) 0.0013(17) 0.0003(15) C7 0.0187(18) 0.0229(17) 0.0250(18) -0.0083(14) -0.0023(15) -0.0016(16) C8 0.022(2) 0.0213(16) 0.0192(17) -0.0016(14) 0.0007(14) 0.0015(15) C9 0.0154(17) 0.0180(16) 0.0180(17) -0.0005(14) 0.0045(14) -0.0013(14) C10 0.0175(18) 0.0187(16) 0.0159(16) -0.0007(14) 0.0006(14) 0.0013(15) C11 0.0194(18) 0.0174(16) 0.0126(15) 0.0012(13) -0.0025(13) -0.0024(14) C12 0.0222(19) 0.0251(18) 0.0221(18) 0.0015(15) 0.0022(15) -0.0015(16) C13 0.0204(18) 0.0184(16) 0.0123(15) 0.0016(13) -0.0031(14) -0.0011(14) C14 0.027(2) 0.0176(16) 0.0189(17) 0.0004(13) -0.0047(16) -0.0017(16) C15 0.024(2) 0.029(2) 0.0227(19) -0.0016(16) -0.0045(16) 0.0028(16) C16 0.032(2) 0.0236(18) 0.0243(19) -0.0044(15) -0.0080(16) 0.0073(17) C17 0.035(2) 0.0179(17) 0.0213(18) -0.0014(15) -0.0087(17) -0.0013(16) C18 0.023(2) 0.0208(17) 0.0198(18) 0.0008(15) -0.0038(15) -0.0043(15) C19 0.0171(17) 0.0190(16) 0.0193(17) -0.0012(15) -0.0036(15) -0.0055(14) C20 0.021(2) 0.0296(19) 0.0201(18) -0.0005(16) -0.0015(15) -0.0009(16) C21 0.023(2) 0.031(2) 0.0238(19) 0.0066(16) -0.0020(15) -0.0006(17) C22 0.019(2) 0.0251(18) 0.030(2) 0.0006(16) -0.0011(16) -0.0038(15) C23 0.024(2) 0.0256(19) 0.026(2) -0.0046(16) 0.0055(16) -0.0044(16) C24 0.0219(19) 0.0227(17) 0.0202(17) 0.0004(15) -0.0007(15) -0.0048(16) C25 0.029(2) 0.0289(19) 0.042(2) 0.0059(18) 0.0069(18) 0.0033(18) N1 0.0205(15) 0.0175(13) 0.0162(13) 0.0025(11) -0.0016(13) -0.0015(13) N2 0.0202(15) 0.0159(13) 0.0166(14) 0.0021(12) -0.0029(12) -0.0007(12) O1 0.0256(14) 0.0218(12) 0.0234(12) 0.0038(10) -0.0016(10) -0.0058(11) O2 0.0286(14) 0.0245(12) 0.0181(11) -0.0051(10) -0.0009(11) -0.0037(11) S1 0.0207(4) 0.0185(4) 0.0165(4) -0.0007(3) -0.0012(4) -0.0032(4) 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 N1 C1 C12 111.9(3) N1 C1 C2 110.4(3) C12 C1 C2 113.5(3) N1 C1 H1 106.9 C12 C1 H1 106.9 C2 C1 H1 106.9 C3 C2 C1 109.3(3) C3 C2 H2A 109.8 C1 C2 H2A 109.8 C3 C2 H2B 109.8 C1 C2 H2B 109.8 H2A C2 H2B 108.3 C10 C3 C4 106.7(3) C10 C3 C2 121.8(3) C4 C3 C2 131.5(3) C9 C4 C5 118.4(3) C9 C4 C3 107.1(3) C5 C4 C3 134.5(3) C6 C5 C4 118.7(3) C6 C5 H5 120.7 C4 C5 H5 120.7 C5 C6 C7 121.8(3) C5 C6 H6 119.1 C7 C6 H6 119.1 C8 C7 C6 121.1(3) C8 C7 H7 119.4 C6 C7 H7 119.4 C7 C8 C9 117.0(3) C7 C8 H8 121.5 C9 C8 H8 121.5 N2 C9 C8 129.5(3) N2 C9 C4 107.5(3) C8 C9 C4 123.0(3) C3 C10 N2 110.4(3) C3 C10 C11 126.8(3) N2 C10 C11 122.6(3) N1 C11 C10 108.0(2) N1 C11 C13 112.7(2) C10 C11 C13 114.3(3) N1 C11 H11 107.2 C10 C11 H11 107.2 C13 C11 H11 107.2 C1 C12 H12A 109.5 C1 C12 H12B 109.5 H12A C12 H12B 109.5 C1 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 C18 C13 C14 118.4(3) C18 C13 C11 119.9(3) C14 C13 C11 121.7(3) C15 C14 C13 120.6(3) C15 C14 H14 119.7 C13 C14 H14 119.7 C14 C15 C16 120.3(3) C14 C15 H15 119.8 C16 C15 H15 119.8 C17 C16 C15 119.4(3) C17 C16 H16 120.3 C15 C16 H16 120.3 C16 C17 C18 120.1(3) C16 C17 H17 120.0 C18 C17 H17 120.0 C13 C18 C17 121.1(3) C13 C18 H18 119.4 C17 C18 H18 119.4 C20 C19 C24 120.4(3) C20 C19 S1 119.4(3) C24 C19 S1 120.0(3) C19 C20 C21 119.4(3) C19 C20 H20 120.3 C21 C20 H20 120.3 C20 C21 C22 121.2(3) C20 C21 H21 119.4 C22 C21 H21 119.4 C21 C22 C23 118.2(3) C21 C22 C25 120.3(3) C23 C22 C25 121.5(3) C24 C23 C22 121.5(3) C24 C23 H23 119.3 C22 C23 H23 119.3 C23 C24 C19 119.3(3) C23 C24 H24 120.3 C19 C24 H24 120.3 C22 C25 H25A 109.5 C22 C25 H25B 109.5 H25A C25 H25B 109.5 C22 C25 H25C 109.5 H25A C25 H25C 109.5 H25B C25 H25C 109.5 C1 N1 C11 121.1(3) C1 N1 S1 115.8(2) C11 N1 S1 120.0(2) C10 N2 C9 108.3(3) C10 N2 H2 125.8 C9 N2 H2 125.8 O2 S1 O1 118.74(14) O2 S1 N1 108.52(14) O1 S1 N1 106.97(14) O2 S1 C19 106.62(15) O1 S1 C19 108.96(15) N1 S1 C19 106.43(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 N1 1.497(4) C1 C12 1.523(5) C1 C2 1.524(4) C1 H1 1.0000 C2 C3 1.500(4) C2 H2A 0.9900 C2 H2B 0.9900 C3 C10 1.356(4) C3 C4 1.435(5) C4 C9 1.409(5) C4 C5 1.410(4) C5 C6 1.379(5) C5 H5 0.9500 C6 C7 1.398(5) C6 H6 0.9500 C7 C8 1.387(4) C7 H7 0.9500 C8 C9 1.396(4) C8 H8 0.9500 C9 N2 1.382(4) C10 N2 1.379(4) C10 C11 1.499(4) C11 N1 1.499(4) C11 C13 1.521(4) C11 H11 1.0000 C12 H12A 0.9800 C12 H12B 0.9800 C12 H12C 0.9800 C13 C18 1.387(4) C13 C14 1.397(5) C14 C15 1.385(5) C14 H14 0.9500 C15 C16 1.391(5) C15 H15 0.9500 C16 C17 1.383(5) C16 H16 0.9500 C17 C18 1.390(5) C17 H17 0.9500 C18 H18 0.9500 C19 C20 1.386(5) C19 C24 1.391(5) C19 S1 1.765(3) C20 C21 1.388(5) C20 H20 0.9500 C21 C22 1.388(5) C21 H21 0.9500 C22 C23 1.395(5) C22 C25 1.508(5) C23 C24 1.378(5) C23 H23 0.9500 C24 H24 0.9500 C25 H25A 0.9800 C25 H25B 0.9800 C25 H25C 0.9800 N1 S1 1.629(3) N2 H2 0.8800 O1 S1 1.439(2) O2 S1 1.433(2)