#------------------------------------------------------------------------------ #$Date: 2016-07-01 13:23:38 +0300 (Fri, 01 Jul 2016) $ #$Revision: 184110 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/90/7119066.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_7119066 loop_ _publ_author_name 'Ming Chen' 'Ning Sun' 'Haoyi Chen' 'Yuanhong Liu' _publ_section_title ; Dioxazoles, a new mild nitrene transfer reagent in gold catalysis: highly efficient synthesis of functionalized oxazoles ; _journal_name_full Chem.Commun. _journal_page_first 6324 _journal_volume 52 _journal_year 2016 _chemical_formula_sum 'C23 H18 N2 O3 S2' _chemical_formula_weight 434.51 _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 mixed _audit_creation_method SHELXL-2013 _audit_update_record ; 2016-02-23 deposited with the CCDC. 2016-04-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 91.235(13) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 18.929(9) _cell_length_b 12.430(6) _cell_length_c 8.472(4) _cell_measurement_reflns_used 1157 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 38.774 _cell_measurement_theta_min 5.411 _cell_volume 1992.9(16) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_solution 'Bruker SHELXTL' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0644 _diffrn_reflns_av_unetI/netI 0.0693 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 11203 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.499 _diffrn_reflns_theta_min 1.960 _exptl_absorpt_coefficient_mu 0.296 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6158 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.448 _exptl_crystal_description prismatic _exptl_crystal_F_000 904 _exptl_crystal_size_max 0.190 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.278 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.052 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 276 _refine_ls_number_reflns 3705 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.995 _refine_ls_R_factor_all 0.0911 _refine_ls_R_factor_gt 0.0529 _refine_ls_shift/su_max 0.038 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0451P)^2^+0.7329P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1062 _refine_ls_wR_factor_ref 0.1218 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2463 _reflns_number_total 3705 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6cc02776h2.cif _cod_data_source_block cd16075 _cod_original_cell_volume 1992.9(17) _cod_database_code 7119066 _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 0.946 _shelx_estimated_absorpt_t_max 0.971 _shelxl_version_number 2013-4 _shelx_res_file ; TITL cd16075 in P2(1)/c CELL 0.71073 18.9288 12.4304 8.4719 90.000 91.235 90.000 ZERR 4.00 0.0085 0.0060 0.0043 0.000 0.013 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O S UNIT 92 72 8 12 8 OMIT 1 0 0 OMIT -3 4 3 OMIT -4 1 5 OMIT 10 3 0 OMIT -3.00 51.00 L.S. 10 ACTA BOND $H FMAP 2 PLAN 20 wpdb -1 size 0.19 0.15 0.10 mpla c17 > c22 mpla c10 > c16 mpla c1 > c6 htab conf WGHT 0.045100 0.732900 FVAR 0.17416 MOLE 1 S1 5 0.423147 0.898884 0.188020 11.00000 0.04319 0.05504 = 0.04786 0.00087 0.01307 0.00797 S2 5 0.154864 1.072803 0.206127 11.00000 0.04157 0.04700 = 0.03865 -0.00199 0.00824 0.00403 N1 3 0.241370 1.059498 0.178025 11.00000 0.03815 0.03205 = 0.03963 0.00025 0.00187 -0.00486 N2 3 0.249181 0.865176 0.238383 11.00000 0.04215 0.03549 = 0.03405 -0.00386 -0.00182 -0.00946 O1 4 0.209471 0.747942 0.420647 11.00000 0.06118 0.04669 = 0.05174 0.00699 0.00369 -0.01793 O2 4 0.138438 1.006996 0.338176 11.00000 0.05588 0.07474 = 0.03983 0.00766 0.01605 0.00554 O3 4 0.142119 1.185757 0.211599 11.00000 0.06051 0.04594 = 0.06629 -0.01262 0.00872 0.00894 C1 1 0.287471 1.139044 0.120817 11.00000 0.04106 0.03639 = 0.03011 -0.00280 0.00078 -0.00492 C2 1 0.274629 1.244091 0.068340 11.00000 0.05920 0.04279 = 0.04635 0.00116 -0.00255 0.00023 AFIX 43 H2 2 0.229530 1.273729 0.069405 11.00000 -1.20000 AFIX 0 C3 1 0.331140 1.301566 0.015316 11.00000 0.07423 0.04090 = 0.04786 0.00542 -0.00049 -0.01177 AFIX 43 H3 2 0.323981 1.371247 -0.021658 11.00000 -1.20000 AFIX 0 C4 1 0.398539 1.258669 0.015343 11.00000 0.06873 0.05668 = 0.05338 0.00616 0.00730 -0.02685 AFIX 43 H4 2 0.435626 1.300129 -0.021427 11.00000 -1.20000 AFIX 0 C5 1 0.411946 1.155617 0.068786 11.00000 0.04700 0.05253 = 0.04462 -0.00312 0.00516 -0.01094 AFIX 43 H5 2 0.457506 1.127580 0.070262 11.00000 -1.20000 AFIX 0 C6 1 0.354875 1.094788 0.120589 11.00000 0.04211 0.04246 = 0.02465 -0.00390 0.00085 -0.00780 C7 1 0.350101 0.983901 0.170073 11.00000 0.03813 0.03653 = 0.02958 -0.00295 0.00514 -0.00031 C8 1 0.281768 0.963014 0.198553 11.00000 0.03973 0.03208 = 0.02893 -0.00189 0.00041 -0.00268 C9 1 0.247038 0.824507 0.387718 11.00000 0.03651 0.03351 = 0.04328 -0.00028 0.00762 0.00250 C10 1 0.295493 0.876747 0.507353 11.00000 0.04291 0.02972 = 0.03112 0.00341 0.00276 -0.00168 C11 1 0.368593 0.872864 0.490802 11.00000 0.04510 0.03050 = 0.03048 0.00246 0.00215 0.00219 C12 1 0.400288 0.812849 0.354773 11.00000 0.04342 0.03998 = 0.04598 -0.00231 0.00383 0.00752 AFIX 23 H12A 2 0.366954 0.758599 0.318109 11.00000 -1.20000 H12B 2 0.442578 0.776007 0.392348 11.00000 -1.20000 AFIX 0 C13 1 0.267162 0.924227 0.639845 11.00000 0.05044 0.04393 = 0.03795 0.00070 0.00962 -0.00034 AFIX 43 H13 2 0.218515 0.923417 0.653014 11.00000 -1.20000 AFIX 0 C14 1 0.310230 0.972655 0.752378 11.00000 0.06704 0.05624 = 0.03093 -0.01282 0.00538 0.00554 AFIX 43 H14 2 0.290766 1.005031 0.840342 11.00000 -1.20000 AFIX 0 C15 1 0.382539 0.972653 0.733300 11.00000 0.06352 0.04768 = 0.03794 -0.00700 -0.00899 -0.00295 AFIX 43 H15 2 0.411865 1.006660 0.807305 11.00000 -1.20000 AFIX 0 C16 1 0.411269 0.922269 0.604616 11.00000 0.04573 0.03994 = 0.04375 0.00543 -0.00318 0.00038 AFIX 43 H16 2 0.460061 0.921387 0.593934 11.00000 -1.20000 AFIX 0 C17 1 0.115995 1.018975 0.033534 11.00000 0.02982 0.04023 = 0.04222 -0.00024 0.00500 0.00419 C18 1 0.082949 0.920418 0.037923 11.00000 0.04549 0.04487 = 0.05442 0.01044 -0.00063 -0.00171 AFIX 43 H18 2 0.079353 0.883223 0.132659 11.00000 -1.20000 AFIX 0 C19 1 0.055362 0.877829 -0.099737 11.00000 0.04973 0.03485 = 0.06629 0.00478 -0.00537 -0.00253 AFIX 43 H19 2 0.032132 0.811971 -0.096292 11.00000 -1.20000 AFIX 0 C20 1 0.061005 0.929599 -0.242905 11.00000 0.03691 0.04334 = 0.05209 -0.00370 -0.00032 0.00946 C21 1 0.092999 1.029702 -0.243321 11.00000 0.04905 0.05675 = 0.04208 0.00699 -0.00307 -0.00100 AFIX 43 H21 2 0.096016 1.067235 -0.337897 11.00000 -1.20000 AFIX 0 C22 1 0.120404 1.074925 -0.107319 11.00000 0.05143 0.04391 = 0.05290 0.00724 0.00286 -0.00936 AFIX 43 H22 2 0.141673 1.142329 -0.109776 11.00000 -1.20000 AFIX 0 C23 1 0.035413 0.876295 -0.393090 11.00000 0.07286 0.05965 = 0.06507 -0.01164 -0.00546 0.00325 AFIX 137 H23A 2 0.074197 0.840468 -0.441930 11.00000 -1.50000 H23B 2 0.016291 0.929709 -0.463825 11.00000 -1.50000 H23C 2 -0.000572 0.824715 -0.369293 11.00000 -1.50000 AFIX 0 H2A 2 0.230053 0.830503 0.162012 11.00000 0.04656 HKLF 4 REM cd16075 in P2(1)/c REM R1 = 0.0529 for 2463 Fo > 4sig(Fo) and 0.0911 for all 3705 data REM 276 parameters refined using 0 restraints END WGHT 0.0491 0.2813 REM Instructions for potential hydrogen bonds HTAB C2 O3 EQIV $1 x, -y+5/2, z-1/2 HTAB C22 O3_$1 EQIV $2 x, -y+3/2, z-1/2 HTAB N2 O1_$2 REM Highest difference peak 0.278, deepest hole -0.236, 1-sigma level 0.052 Q1 1 0.3694 0.9024 0.1771 11.00000 0.05 0.28 Q2 1 0.4783 0.9074 0.1665 11.00000 0.05 0.27 Q3 1 0.3853 0.9620 0.2248 11.00000 0.05 0.26 Q4 1 0.2048 1.0625 0.1781 11.00000 0.05 0.26 Q5 1 0.2498 1.0104 0.1584 11.00000 0.05 0.23 Q6 1 0.2985 0.9787 0.6433 11.00000 0.05 0.22 Q7 1 -0.0282 0.9051 -0.4094 11.00000 0.05 0.21 Q8 1 0.0674 1.0005 0.0318 11.00000 0.05 0.21 Q9 1 0.4210 0.8805 0.0556 11.00000 0.05 0.20 Q10 1 0.2796 0.9380 0.5226 11.00000 0.05 0.20 Q11 1 0.2565 1.1009 0.1484 11.00000 0.05 0.20 Q12 1 0.4677 0.8018 0.3492 11.00000 0.05 0.20 Q13 1 0.1307 1.0615 0.0843 11.00000 0.05 0.20 Q14 1 0.1431 1.0236 0.1195 11.00000 0.05 0.19 Q15 1 0.3862 0.9397 0.4976 11.00000 0.05 0.19 Q16 1 0.3915 0.8223 0.5025 11.00000 0.05 0.19 Q17 1 0.0684 1.0773 -0.1407 11.00000 0.05 0.19 Q18 1 0.0432 1.0205 -0.2656 11.00000 0.05 0.19 Q19 1 0.3276 0.9771 0.2323 11.00000 0.05 0.19 Q20 1 0.1321 1.1466 0.2071 11.00000 0.05 0.18 ; _shelx_res_checksum 7959 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' '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_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 0.42315(4) 0.89888(7) 0.18802(10) 0.0485(3) Uani 1 1 d . . . . . S2 S 0.15486(4) 1.07280(7) 0.20613(10) 0.0423(2) Uani 1 1 d . . . . . N1 N 0.24137(12) 1.05950(18) 0.1780(3) 0.0366(6) Uani 1 1 d . . . . . N2 N 0.24918(13) 0.8652(2) 0.2384(3) 0.0373(6) Uani 1 1 d . . . . . O1 O 0.20947(12) 0.74794(18) 0.4206(3) 0.0532(6) Uani 1 1 d . . . . . O2 O 0.13844(12) 1.00700(19) 0.3382(3) 0.0566(7) Uani 1 1 d . . . . . O3 O 0.14212(12) 1.18576(18) 0.2116(3) 0.0575(6) Uani 1 1 d . . . . . C1 C 0.28747(16) 1.1390(2) 0.1208(3) 0.0359(7) Uani 1 1 d . . . . . C2 C 0.27463(19) 1.2441(3) 0.0683(4) 0.0495(9) Uani 1 1 d . . . . . H2 H 0.2295 1.2737 0.0694 0.059 Uiso 1 1 calc R U . . . C3 C 0.3311(2) 1.3016(3) 0.0153(4) 0.0544(9) Uani 1 1 d . . . . . H3 H 0.3240 1.3712 -0.0217 0.065 Uiso 1 1 calc R U . . . C4 C 0.3985(2) 1.2587(3) 0.0153(4) 0.0595(10) Uani 1 1 d . . . . . H4 H 0.4356 1.3001 -0.0214 0.071 Uiso 1 1 calc R U . . . C5 C 0.41195(18) 1.1556(3) 0.0688(4) 0.0480(9) Uani 1 1 d . . . . . H5 H 0.4575 1.1276 0.0703 0.058 Uiso 1 1 calc R U . . . C6 C 0.35487(16) 1.0948(2) 0.1206(3) 0.0364(7) Uani 1 1 d . . . . . C7 C 0.35010(15) 0.9839(2) 0.1701(3) 0.0347(7) Uani 1 1 d . . . . . C8 C 0.28177(15) 0.9630(2) 0.1986(3) 0.0336(7) Uani 1 1 d . . . . . C9 C 0.24704(16) 0.8245(2) 0.3877(4) 0.0377(7) Uani 1 1 d . . . . . C10 C 0.29549(15) 0.8767(2) 0.5074(3) 0.0346(7) Uani 1 1 d . . . . . C11 C 0.36859(16) 0.8729(2) 0.4908(3) 0.0353(7) Uani 1 1 d . . . . . C12 C 0.40029(16) 0.8128(2) 0.3548(4) 0.0431(8) Uani 1 1 d . . . . . H12A H 0.3670 0.7586 0.3181 0.052 Uiso 1 1 calc R U . . . H12B H 0.4426 0.7760 0.3923 0.052 Uiso 1 1 calc R U . . . C13 C 0.26716(18) 0.9242(2) 0.6398(4) 0.0440(8) Uani 1 1 d . . . . . H13 H 0.2185 0.9234 0.6530 0.053 Uiso 1 1 calc R U . . . C14 C 0.31023(19) 0.9727(3) 0.7524(4) 0.0513(9) Uani 1 1 d . . . . . H14 H 0.2908 1.0050 0.8403 0.062 Uiso 1 1 calc R U . . . C15 C 0.38254(19) 0.9727(3) 0.7333(4) 0.0499(9) Uani 1 1 d . . . . . H15 H 0.4119 1.0067 0.8073 0.060 Uiso 1 1 calc R U . . . C16 C 0.41127(17) 0.9223(2) 0.6046(4) 0.0432(8) Uani 1 1 d . . . . . H16 H 0.4601 0.9214 0.5939 0.052 Uiso 1 1 calc R U . . . C17 C 0.11599(15) 1.0190(2) 0.0335(4) 0.0374(7) Uani 1 1 d . . . . . C18 C 0.08295(17) 0.9204(3) 0.0379(4) 0.0483(9) Uani 1 1 d . . . . . H18 H 0.0794 0.8832 0.1327 0.058 Uiso 1 1 calc R U . . . C19 C 0.05536(17) 0.8778(3) -0.0997(4) 0.0504(9) Uani 1 1 d . . . . . H19 H 0.0321 0.8120 -0.0963 0.060 Uiso 1 1 calc R U . . . C20 C 0.06101(16) 0.9296(3) -0.2429(4) 0.0441(8) Uani 1 1 d . . . . . C21 C 0.09300(17) 1.0297(3) -0.2433(4) 0.0494(9) Uani 1 1 d . . . . . H21 H 0.0960 1.0672 -0.3379 0.059 Uiso 1 1 calc R U . . . C22 C 0.12040(17) 1.0749(3) -0.1073(4) 0.0494(9) Uani 1 1 d . . . . . H22 H 0.1417 1.1423 -0.1098 0.059 Uiso 1 1 calc R U . . . C23 C 0.0354(2) 0.8763(3) -0.3931(5) 0.0660(11) Uani 1 1 d . . . . . H23A H 0.0742 0.8405 -0.4419 0.099 Uiso 1 1 calc R U . . . H23B H 0.0163 0.9297 -0.4638 0.099 Uiso 1 1 calc R U . . . H23C H -0.0006 0.8247 -0.3693 0.099 Uiso 1 1 calc R U . . . H2A H 0.2301(16) 0.831(3) 0.162(4) 0.047(10) Uiso 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 S1 0.0432(5) 0.0550(6) 0.0479(5) 0.0009(4) 0.0131(4) 0.0080(4) S2 0.0416(5) 0.0470(5) 0.0386(5) -0.0020(4) 0.0082(4) 0.0040(4) N1 0.0381(15) 0.0321(14) 0.0396(15) 0.0003(11) 0.0019(12) -0.0049(12) N2 0.0422(16) 0.0355(15) 0.0340(16) -0.0039(12) -0.0018(12) -0.0095(12) O1 0.0612(15) 0.0467(14) 0.0517(15) 0.0070(11) 0.0037(12) -0.0179(12) O2 0.0559(14) 0.0747(17) 0.0398(14) 0.0077(12) 0.0160(11) 0.0055(13) O3 0.0605(15) 0.0459(14) 0.0663(17) -0.0126(12) 0.0087(12) 0.0089(12) C1 0.0411(18) 0.0364(18) 0.0301(17) -0.0028(13) 0.0008(13) -0.0049(15) C2 0.059(2) 0.043(2) 0.046(2) 0.0012(16) -0.0026(17) 0.0002(17) C3 0.074(3) 0.041(2) 0.048(2) 0.0054(16) -0.0005(19) -0.012(2) C4 0.069(3) 0.057(2) 0.053(2) 0.0062(18) 0.0073(19) -0.027(2) C5 0.047(2) 0.053(2) 0.045(2) -0.0031(16) 0.0052(16) -0.0109(17) C6 0.0421(19) 0.0425(18) 0.0247(16) -0.0039(13) 0.0009(13) -0.0078(15) C7 0.0381(19) 0.0365(17) 0.0296(16) -0.0029(13) 0.0051(13) -0.0003(14) C8 0.0397(18) 0.0321(17) 0.0289(16) -0.0019(13) 0.0004(13) -0.0027(14) C9 0.0365(18) 0.0335(18) 0.043(2) -0.0003(14) 0.0076(14) 0.0025(15) C10 0.0429(19) 0.0297(16) 0.0311(17) 0.0034(13) 0.0028(13) -0.0017(14) C11 0.0451(19) 0.0305(16) 0.0305(17) 0.0025(13) 0.0022(14) 0.0022(14) C12 0.0434(19) 0.0400(19) 0.046(2) -0.0023(15) 0.0038(15) 0.0075(15) C13 0.050(2) 0.0439(19) 0.0380(19) 0.0007(15) 0.0096(15) -0.0003(16) C14 0.067(3) 0.056(2) 0.0309(18) -0.0128(16) 0.0054(17) 0.0055(19) C15 0.064(2) 0.048(2) 0.038(2) -0.0070(16) -0.0090(17) -0.0029(18) C16 0.046(2) 0.0399(18) 0.044(2) 0.0054(15) -0.0032(15) 0.0004(15) C17 0.0298(16) 0.0402(18) 0.0422(19) -0.0002(15) 0.0050(14) 0.0042(14) C18 0.045(2) 0.045(2) 0.054(2) 0.0104(17) -0.0006(16) -0.0017(17) C19 0.050(2) 0.0349(19) 0.066(3) 0.0048(17) -0.0054(18) -0.0025(16) C20 0.0369(19) 0.043(2) 0.052(2) -0.0037(16) -0.0003(15) 0.0095(16) C21 0.049(2) 0.057(2) 0.042(2) 0.0070(17) -0.0031(16) -0.0010(18) C22 0.051(2) 0.044(2) 0.053(2) 0.0072(17) 0.0029(17) -0.0094(16) C23 0.073(3) 0.060(2) 0.065(3) -0.012(2) -0.005(2) 0.003(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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 C7 S1 C12 102.77(14) . . O2 S2 O3 119.98(15) . . O2 S2 N1 106.65(13) . . O3 S2 N1 105.64(13) . . O2 S2 C17 109.90(15) . . O3 S2 C17 109.53(15) . . N1 S2 C17 103.80(13) . . C1 N1 C8 107.2(2) . . C1 N1 S2 126.6(2) . . C8 N1 S2 126.12(19) . . C9 N2 C8 124.4(3) . . C9 N2 H2A 120(2) . . C8 N2 H2A 116(2) . . C6 C1 C2 121.5(3) . . C6 C1 N1 107.3(3) . . C2 C1 N1 131.2(3) . . C3 C2 C1 117.3(3) . . C3 C2 H2 121.3 . . C1 C2 H2 121.3 . . C2 C3 C4 121.7(3) . . C2 C3 H3 119.1 . . C4 C3 H3 119.1 . . C3 C4 C5 121.4(3) . . C3 C4 H4 119.3 . . C5 C4 H4 119.3 . . C4 C5 C6 117.9(3) . . C4 C5 H5 121.1 . . C6 C5 H5 121.1 . . C1 C6 C5 120.2(3) . . C1 C6 C7 108.3(3) . . C5 C6 C7 131.4(3) . . C8 C7 C6 107.6(3) . . C8 C7 S1 129.1(2) . . C6 C7 S1 123.3(2) . . C7 C8 N2 129.6(3) . . C7 C8 N1 109.2(2) . . N2 C8 N1 121.2(2) . . O1 C9 N2 121.9(3) . . O1 C9 C10 122.2(3) . . N2 C9 C10 115.9(3) . . C13 C10 C11 119.9(3) . . C13 C10 C9 119.3(3) . . C11 C10 C9 120.7(3) . . C16 C11 C10 118.6(3) . . C16 C11 C12 121.0(3) . . C10 C11 C12 120.4(3) . . C11 C12 S1 113.9(2) . . C11 C12 H12A 108.8 . . S1 C12 H12A 108.8 . . C11 C12 H12B 108.8 . . S1 C12 H12B 108.8 . . H12A C12 H12B 107.7 . . C14 C13 C10 120.8(3) . . C14 C13 H13 119.6 . . C10 C13 H13 119.6 . . C13 C14 C15 119.4(3) . . C13 C14 H14 120.3 . . C15 C14 H14 120.3 . . C16 C15 C14 120.1(3) . . C16 C15 H15 120.0 . . C14 C15 H15 120.0 . . C15 C16 C11 121.1(3) . . C15 C16 H16 119.4 . . C11 C16 H16 119.4 . . C18 C17 C22 120.4(3) . . C18 C17 S2 120.0(3) . . C22 C17 S2 119.6(2) . . C19 C18 C17 119.0(3) . . C19 C18 H18 120.5 . . C17 C18 H18 120.5 . . C18 C19 C20 122.1(3) . . C18 C19 H19 118.9 . . C20 C19 H19 118.9 . . C19 C20 C21 117.6(3) . . C19 C20 C23 120.6(3) . . C21 C20 C23 121.8(3) . . C22 C21 C20 121.5(3) . . C22 C21 H21 119.2 . . C20 C21 H21 119.2 . . C21 C22 C17 119.2(3) . . C21 C22 H22 120.4 . . C17 C22 H22 120.4 . . C20 C23 H23A 109.5 . . C20 C23 H23B 109.5 . . H23A C23 H23B 109.5 . . C20 C23 H23C 109.5 . . H23A C23 H23C 109.5 . . H23B C23 H23C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 S1 C7 1.744(3) . S1 C12 1.831(3) . S2 O2 1.426(2) . S2 O3 1.426(2) . S2 N1 1.668(3) . S2 C17 1.755(3) . N1 C1 1.412(4) . N1 C8 1.431(4) . N2 C9 1.364(4) . N2 C8 1.408(4) . N2 H2A 0.85(3) . O1 C9 1.224(3) . C1 C6 1.389(4) . C1 C2 1.399(4) . C2 C3 1.370(4) . C2 H2 0.9300 . C3 C4 1.383(5) . C3 H3 0.9300 . C4 C5 1.380(5) . C4 H4 0.9300 . C5 C6 1.397(4) . C5 H5 0.9300 . C6 C7 1.444(4) . C7 C8 1.346(4) . C9 C10 1.500(4) . C10 C13 1.386(4) . C10 C11 1.395(4) . C11 C16 1.388(4) . C11 C12 1.508(4) . C12 H12A 0.9700 . C12 H12B 0.9700 . C13 C14 1.379(4) . C13 H13 0.9300 . C14 C15 1.382(5) . C14 H14 0.9300 . C15 C16 1.379(4) . C15 H15 0.9300 . C16 H16 0.9300 . C17 C18 1.376(4) . C17 C22 1.385(4) . C18 C19 1.374(5) . C18 H18 0.9300 . C19 C20 1.379(5) . C19 H19 0.9300 . C20 C21 1.384(4) . C20 C23 1.505(5) . C21 C22 1.374(4) . C21 H21 0.9300 . C22 H22 0.9300 . C23 H23A 0.9600 . C23 H23B 0.9600 . C23 H23C 0.9600 . 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 O2 S2 N1 C1 -147.3(2) . . . . O3 S2 N1 C1 -18.6(3) . . . . C17 S2 N1 C1 96.6(3) . . . . O2 S2 N1 C8 36.7(3) . . . . O3 S2 N1 C8 165.5(2) . . . . C17 S2 N1 C8 -79.3(3) . . . . C8 N1 C1 C6 -5.2(3) . . . . S2 N1 C1 C6 178.2(2) . . . . C8 N1 C1 C2 173.8(3) . . . . S2 N1 C1 C2 -2.8(5) . . . . C6 C1 C2 C3 0.5(5) . . . . N1 C1 C2 C3 -178.4(3) . . . . C1 C2 C3 C4 -0.9(5) . . . . C2 C3 C4 C5 0.1(5) . . . . C3 C4 C5 C6 1.1(5) . . . . C2 C1 C6 C5 0.7(4) . . . . N1 C1 C6 C5 179.8(3) . . . . C2 C1 C6 C7 -175.9(3) . . . . N1 C1 C6 C7 3.2(3) . . . . C4 C5 C6 C1 -1.5(5) . . . . C4 C5 C6 C7 174.2(3) . . . . C1 C6 C7 C8 0.1(3) . . . . C5 C6 C7 C8 -176.0(3) . . . . C1 C6 C7 S1 -179.3(2) . . . . C5 C6 C7 S1 4.6(5) . . . . C12 S1 C7 C8 -33.1(3) . . . . C12 S1 C7 C6 146.2(2) . . . . C6 C7 C8 N2 174.9(3) . . . . S1 C7 C8 N2 -5.7(5) . . . . C6 C7 C8 N1 -3.4(3) . . . . S1 C7 C8 N1 176.0(2) . . . . C9 N2 C8 C7 83.3(4) . . . . C9 N2 C8 N1 -98.5(3) . . . . C1 N1 C8 C7 5.4(3) . . . . S2 N1 C8 C7 -178.0(2) . . . . C1 N1 C8 N2 -173.1(2) . . . . S2 N1 C8 N2 3.5(4) . . . . C8 N2 C9 O1 168.9(3) . . . . C8 N2 C9 C10 -13.3(4) . . . . O1 C9 C10 C13 -61.6(4) . . . . N2 C9 C10 C13 120.6(3) . . . . O1 C9 C10 C11 114.9(3) . . . . N2 C9 C10 C11 -62.9(4) . . . . C13 C10 C11 C16 -3.4(4) . . . . C9 C10 C11 C16 -179.9(3) . . . . C13 C10 C11 C12 174.5(3) . . . . C9 C10 C11 C12 -2.0(4) . . . . C16 C11 C12 S1 -84.5(3) . . . . C10 C11 C12 S1 97.6(3) . . . . C7 S1 C12 C11 -43.2(3) . . . . C11 C10 C13 C14 3.2(5) . . . . C9 C10 C13 C14 179.8(3) . . . . C10 C13 C14 C15 -0.7(5) . . . . C13 C14 C15 C16 -1.6(5) . . . . C14 C15 C16 C11 1.3(5) . . . . C10 C11 C16 C15 1.2(4) . . . . C12 C11 C16 C15 -176.8(3) . . . . O2 S2 C17 C18 -6.8(3) . . . . O3 S2 C17 C18 -140.7(3) . . . . N1 S2 C17 C18 106.9(3) . . . . O2 S2 C17 C22 174.8(2) . . . . O3 S2 C17 C22 41.0(3) . . . . N1 S2 C17 C22 -71.4(3) . . . . C22 C17 C18 C19 0.9(5) . . . . S2 C17 C18 C19 -177.4(2) . . . . C17 C18 C19 C20 1.4(5) . . . . C18 C19 C20 C21 -2.9(5) . . . . C18 C19 C20 C23 174.9(3) . . . . C19 C20 C21 C22 2.1(5) . . . . C23 C20 C21 C22 -175.7(3) . . . . C20 C21 C22 C17 0.1(5) . . . . C18 C17 C22 C21 -1.6(5) . . . . S2 C17 C22 C21 176.7(2) . . . .