#------------------------------------------------------------------------------ #$Date: 2016-07-01 13:23:38 +0300 (Fri, 01 Jul 2016) $ #$Revision: 184110 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/90/7119065.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_7119065 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 'C22 H18 N2 O3 S' _chemical_formula_weight 390.44 _chemical_name_systematic ; ? ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2013 _audit_update_record ; 2016-01-27 deposited with the CCDC. 2016-04-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 92.321(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.4353(13) _cell_length_b 17.316(2) _cell_length_c 11.6428(17) _cell_measurement_reflns_used 2774 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 50.398 _cell_measurement_theta_min 4.705 _cell_volume 1900.7(4) _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 1.000 _diffrn_measured_fraction_theta_max 1.000 _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 0.0473 _diffrn_reflns_av_unetI/netI 0.0456 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 11248 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.999 _diffrn_reflns_theta_min 2.109 _exptl_absorpt_coefficient_mu 0.196 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.364 _exptl_crystal_description prismatic _exptl_crystal_F_000 816 _exptl_crystal_size_max 0.240 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.170 _refine_diff_density_max 0.314 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.070 _refine_ls_extinction_coef 0.0183(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 1.038 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 255 _refine_ls_number_reflns 3737 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.038 _refine_ls_R_factor_all 0.0614 _refine_ls_R_factor_gt 0.0465 _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^)+(0.0661P)^2^+0.2201P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1159 _refine_ls_wR_factor_ref 0.1255 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2885 _reflns_number_total 3737 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6cc02776h2.cif _cod_data_source_block cd15151 _cod_original_cell_volume 1900.7(5) _cod_database_code 7119065 _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 0.954 _shelx_estimated_absorpt_t_max 0.967 _shelxl_version_number 2013-4 _shelx_res_file ; TITL cd15151 in P2(1)/n CELL 0.71073 9.4353 17.3162 11.6428 90.000 92.321 90.000 ZERR 4.00 0.0013 0.0024 0.0017 0.000 0.003 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N O S UNIT 88 72 8 12 4 OMIT -3.00 52.00 L.S. 10 ACTA BOND $H FMAP 2 PLAN 20 HTAB C22 N1 HTAB C21 N1 size 0.24 0.20 0.17 wpdb -1 mpla c10 > c15 mpla n1 o1 c1 c2 c3 mpla c4 > c9 mpla c16 > c21 mpla c10 > c15 htab conf HTAB C21 N1 WGHT 0.066100 0.220100 EXTI 0.018290 FVAR 0.18031 MOLE 1 S1 5 0.865661 0.168191 1.146823 11.00000 0.04976 0.05274 = 0.03817 0.00835 -0.00511 -0.00649 N1 3 0.715785 0.183459 0.891037 11.00000 0.04486 0.05066 = 0.03275 -0.00055 -0.00113 -0.00500 N2 3 0.712854 0.207975 1.099014 11.00000 0.04655 0.05170 = 0.03227 -0.00270 -0.00382 -0.00585 O1 4 0.516805 0.115208 0.868476 11.00000 0.04215 0.04529 = 0.03295 -0.00150 -0.00122 -0.00382 O2 4 0.844850 0.087296 1.137886 11.00000 0.07503 0.05070 = 0.08863 0.02427 -0.01796 -0.01139 O3 4 0.901199 0.202104 1.255699 11.00000 0.06261 0.10814 = 0.03744 -0.00306 -0.01180 -0.00255 C1 1 0.652382 0.175137 0.995685 11.00000 0.04489 0.04494 = 0.03105 -0.00052 -0.00178 -0.00119 C2 1 0.531547 0.133423 0.983936 11.00000 0.04160 0.04210 = 0.03115 -0.00215 -0.00087 0.00255 C3 1 0.631088 0.146704 0.818711 11.00000 0.04163 0.04058 = 0.03619 0.00198 0.00045 -0.00035 C4 1 0.645405 0.136959 0.695886 11.00000 0.04399 0.04192 = 0.03374 0.00093 -0.00051 0.00507 C5 1 0.763785 0.166268 0.643725 11.00000 0.04248 0.07362 = 0.04239 0.00043 -0.00091 0.00113 AFIX 43 H5 2 0.834572 0.190703 0.688171 11.00000 -1.20000 AFIX 0 C6 1 0.777404 0.159484 0.526553 11.00000 0.05185 0.09073 = 0.04603 0.00710 0.01340 0.00975 AFIX 43 H6 2 0.856657 0.179633 0.492221 11.00000 -1.20000 AFIX 0 C7 1 0.673080 0.122719 0.460519 11.00000 0.08007 0.06862 = 0.03423 -0.00229 0.00798 0.01784 AFIX 43 H7 2 0.682171 0.117825 0.381614 11.00000 -1.20000 AFIX 0 C8 1 0.555946 0.093388 0.511305 11.00000 0.08041 0.05159 = 0.03949 -0.00733 -0.00640 -0.00415 AFIX 43 H8 2 0.485905 0.068688 0.466410 11.00000 -1.20000 AFIX 0 C9 1 0.540875 0.100155 0.628615 11.00000 0.05863 0.04732 = 0.04018 0.00100 -0.00068 -0.00728 AFIX 43 H9 2 0.461061 0.080137 0.662289 11.00000 -1.20000 AFIX 0 C10 1 0.424388 0.104627 1.058860 11.00000 0.03878 0.04633 = 0.03761 0.00468 0.00011 0.00449 C11 1 0.327149 0.048983 1.021578 11.00000 0.04499 0.04758 = 0.04970 0.00327 0.00276 0.00139 AFIX 43 H11 2 0.330222 0.029675 0.947183 11.00000 -1.20000 AFIX 0 C12 1 0.225886 0.022045 1.093995 11.00000 0.04837 0.05290 = 0.07551 0.01190 0.00702 -0.00203 AFIX 43 H12 2 0.160602 -0.014767 1.067597 11.00000 -1.20000 AFIX 0 C13 1 0.220670 0.048958 1.204088 11.00000 0.05094 0.08975 = 0.06267 0.02257 0.01676 0.00563 AFIX 43 H13 2 0.152433 0.030454 1.252544 11.00000 -1.20000 AFIX 0 C14 1 0.317027 0.103586 1.242696 11.00000 0.06087 0.11354 = 0.04250 0.00054 0.01202 0.00423 AFIX 43 H14 2 0.314091 0.121776 1.317719 11.00000 -1.20000 AFIX 0 C15 1 0.417736 0.131569 1.171326 11.00000 0.05374 0.08124 = 0.04363 -0.00679 0.00615 -0.00608 AFIX 43 H15 2 0.481905 0.168767 1.198330 11.00000 -1.20000 AFIX 0 C16 1 0.686012 0.289567 1.119980 11.00000 0.03748 0.05377 = 0.04003 -0.00832 0.00338 -0.00606 C17 1 0.670287 0.315493 1.230965 11.00000 0.05918 0.07295 = 0.04063 -0.01014 0.00341 -0.00917 AFIX 43 H17 2 0.678041 0.281305 1.292501 11.00000 -1.20000 AFIX 0 C18 1 0.642881 0.392875 1.249534 11.00000 0.05993 0.08148 = 0.06045 -0.03365 0.00972 -0.00904 AFIX 43 H18 2 0.632540 0.410571 1.324146 11.00000 -1.20000 AFIX 0 C19 1 0.630733 0.443885 1.159571 11.00000 0.05932 0.06164 = 0.08077 -0.02350 0.00840 -0.00163 AFIX 43 H19 2 0.614469 0.496003 1.173122 11.00000 -1.20000 AFIX 0 C20 1 0.642802 0.417295 1.049362 11.00000 0.07023 0.05710 = 0.07009 -0.00250 0.00651 0.00415 AFIX 43 H20 2 0.632342 0.451404 0.987902 11.00000 -1.20000 AFIX 0 C21 1 0.670370 0.340253 1.029000 11.00000 0.05930 0.05455 = 0.04438 -0.00629 0.00613 0.00111 AFIX 43 H21 2 0.678362 0.322612 0.954094 11.00000 -1.20000 AFIX 0 C22 1 0.993925 0.195931 1.050491 11.00000 0.05014 0.05647 = 0.05237 0.00178 0.00360 0.00011 AFIX 137 H22A 2 1.085415 0.178008 1.077988 11.00000 -1.50000 H22B 2 0.995235 0.251206 1.044271 11.00000 -1.50000 H22C 2 0.971479 0.173795 0.976375 11.00000 -1.50000 AFIX 0 HKLF 4 REM cd15151 in P2(1)/n REM R1 = 0.0465 for 2885 Fo > 4sig(Fo) and 0.0614 for all 3737 data REM 255 parameters refined using 0 restraints END WGHT 0.0629 0.2568 REM Instructions for potential hydrogen bonds HTAB C21 N1 HTAB C22 N1 REM Highest difference peak 0.314, deepest hole -0.317, 1-sigma level 0.070 Q1 1 0.9358 0.1930 1.0986 11.00000 0.05 0.31 Q2 1 0.7224 0.2492 1.1095 11.00000 0.05 0.29 Q3 1 0.7790 0.1969 1.1208 11.00000 0.05 0.27 Q4 1 0.6811 0.1964 1.0565 11.00000 0.05 0.26 Q5 1 0.8932 0.2185 1.2134 11.00000 0.05 0.22 Q6 1 0.8996 0.2181 1.2760 11.00000 0.05 0.21 Q7 1 0.4130 0.0551 1.0551 11.00000 0.05 0.19 Q8 1 0.8240 0.2209 1.2807 11.00000 0.05 0.19 Q9 1 0.7723 0.2226 0.8670 11.00000 0.05 0.19 Q10 1 0.3189 0.0164 1.0776 11.00000 0.05 0.19 Q11 1 0.7277 0.2584 1.2946 11.00000 0.05 0.19 Q12 1 0.3162 -0.0023 0.4017 11.00000 0.05 0.18 Q13 1 0.9604 0.2235 1.0156 11.00000 0.05 0.18 Q14 1 1.0636 0.2366 1.0840 11.00000 0.05 0.18 Q15 1 0.8559 0.2180 0.4862 11.00000 0.05 0.17 Q16 1 0.8642 0.0582 1.1412 11.00000 0.05 0.17 Q17 1 0.6427 0.4902 1.2382 11.00000 0.05 0.17 Q18 1 0.6433 0.0793 0.5058 11.00000 0.05 0.17 Q19 1 0.6672 0.5282 1.1174 11.00000 0.05 0.17 Q20 1 0.4778 0.2113 1.1747 11.00000 0.05 0.16 ; _shelx_res_checksum 46340 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 0.86566(5) 0.16819(3) 1.14682(4) 0.04708(19) Uani 1 1 d . . . . . N1 N 0.71579(16) 0.18346(9) 0.89104(12) 0.0428(4) Uani 1 1 d . . . . . N2 N 0.71285(16) 0.20797(9) 1.09901(12) 0.0437(4) Uani 1 1 d . . . . . O1 O 0.51680(13) 0.11521(7) 0.86848(10) 0.0402(3) Uani 1 1 d . . . . . O2 O 0.84485(18) 0.08730(9) 1.13789(15) 0.0720(5) Uani 1 1 d . . . . . O3 O 0.90120(17) 0.20210(10) 1.25570(12) 0.0698(5) Uani 1 1 d . . . . . C1 C 0.6524(2) 0.17514(10) 0.99568(15) 0.0404(4) Uani 1 1 d . . . . . C2 C 0.53155(19) 0.13342(10) 0.98394(15) 0.0383(4) Uani 1 1 d . . . . . C3 C 0.6311(2) 0.14670(11) 0.81871(15) 0.0395(4) Uani 1 1 d . . . . . C4 C 0.6454(2) 0.13696(10) 0.69589(15) 0.0399(4) Uani 1 1 d . . . . . C5 C 0.7638(2) 0.16627(13) 0.64372(17) 0.0529(5) Uani 1 1 d . . . . . H5 H 0.8346 0.1907 0.6882 0.063 Uiso 1 1 calc R U . . . C6 C 0.7774(2) 0.15948(15) 0.52655(18) 0.0626(6) Uani 1 1 d . . . . . H6 H 0.8567 0.1796 0.4922 0.075 Uiso 1 1 calc R U . . . C7 C 0.6731(3) 0.12272(13) 0.46052(18) 0.0608(6) Uani 1 1 d . . . . . H7 H 0.6822 0.1178 0.3816 0.073 Uiso 1 1 calc R U . . . C8 C 0.5559(3) 0.09339(12) 0.51130(18) 0.0574(6) Uani 1 1 d . . . . . H8 H 0.4859 0.0687 0.4664 0.069 Uiso 1 1 calc R U . . . C9 C 0.5409(2) 0.10016(11) 0.62861(16) 0.0488(5) Uani 1 1 d . . . . . H9 H 0.4611 0.0801 0.6623 0.059 Uiso 1 1 calc R U . . . C10 C 0.42439(19) 0.10463(11) 1.05886(15) 0.0409(4) Uani 1 1 d . . . . . C11 C 0.3271(2) 0.04898(11) 1.02158(18) 0.0474(5) Uani 1 1 d . . . . . H11 H 0.3302 0.0297 0.9472 0.057 Uiso 1 1 calc R U . . . C12 C 0.2259(2) 0.02205(13) 1.0940(2) 0.0588(6) Uani 1 1 d . . . . . H12 H 0.1606 -0.0148 1.0676 0.071 Uiso 1 1 calc R U . . . C13 C 0.2207(2) 0.04896(15) 1.2041(2) 0.0674(7) Uani 1 1 d . . . . . H13 H 0.1524 0.0305 1.2525 0.081 Uiso 1 1 calc R U . . . C14 C 0.3170(3) 0.10359(17) 1.2427(2) 0.0720(7) Uani 1 1 d . . . . . H14 H 0.3141 0.1218 1.3177 0.086 Uiso 1 1 calc R U . . . C15 C 0.4177(2) 0.13157(14) 1.17133(18) 0.0594(6) Uani 1 1 d . . . . . H15 H 0.4819 0.1688 1.1983 0.071 Uiso 1 1 calc R U . . . C16 C 0.68601(19) 0.28957(12) 1.11998(16) 0.0437(5) Uani 1 1 d . . . . . C17 C 0.6703(2) 0.31549(14) 1.23096(18) 0.0575(6) Uani 1 1 d . . . . . H17 H 0.6780 0.2813 1.2925 0.069 Uiso 1 1 calc R U . . . C18 C 0.6429(2) 0.39287(15) 1.2495(2) 0.0671(7) Uani 1 1 d . . . . . H18 H 0.6325 0.4106 1.3241 0.081 Uiso 1 1 calc R U . . . C19 C 0.6307(2) 0.44388(15) 1.1596(2) 0.0671(7) Uani 1 1 d . . . . . H19 H 0.6145 0.4960 1.1731 0.081 Uiso 1 1 calc R U . . . C20 C 0.6428(3) 0.41730(14) 1.0494(2) 0.0657(6) Uani 1 1 d . . . . . H20 H 0.6323 0.4514 0.9879 0.079 Uiso 1 1 calc R U . . . C21 C 0.6704(2) 0.34025(12) 1.02900(18) 0.0526(5) Uani 1 1 d . . . . . H21 H 0.6784 0.3226 0.9541 0.063 Uiso 1 1 calc R U . . . C22 C 0.9939(2) 0.19593(13) 1.05049(18) 0.0530(5) Uani 1 1 d . . . . . H22A H 1.0854 0.1780 1.0780 0.079 Uiso 1 1 calc R U . . . H22B H 0.9952 0.2512 1.0443 0.079 Uiso 1 1 calc R U . . . H22C H 0.9715 0.1738 0.9764 0.079 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0498(3) 0.0527(3) 0.0382(3) 0.0083(2) -0.0051(2) -0.0065(2) N1 0.0449(9) 0.0507(10) 0.0327(8) -0.0005(7) -0.0011(7) -0.0050(7) N2 0.0466(9) 0.0517(10) 0.0323(8) -0.0027(7) -0.0038(7) -0.0058(7) O1 0.0422(7) 0.0453(7) 0.0330(7) -0.0015(5) -0.0012(5) -0.0038(6) O2 0.0750(11) 0.0507(10) 0.0886(12) 0.0243(8) -0.0180(9) -0.0114(8) O3 0.0626(9) 0.1081(13) 0.0374(8) -0.0031(8) -0.0118(7) -0.0026(9) C1 0.0449(10) 0.0449(11) 0.0310(9) -0.0005(8) -0.0018(8) -0.0012(8) C2 0.0416(10) 0.0421(11) 0.0312(9) -0.0022(7) -0.0009(8) 0.0026(8) C3 0.0416(10) 0.0406(10) 0.0362(9) 0.0020(8) 0.0005(8) -0.0003(8) C4 0.0440(10) 0.0419(10) 0.0337(9) 0.0009(8) -0.0005(8) 0.0051(8) C5 0.0425(11) 0.0736(15) 0.0424(11) 0.0004(10) -0.0009(9) 0.0011(10) C6 0.0519(13) 0.0907(18) 0.0460(12) 0.0071(11) 0.0134(10) 0.0098(12) C7 0.0801(16) 0.0686(15) 0.0342(11) -0.0023(10) 0.0080(11) 0.0178(12) C8 0.0804(16) 0.0516(13) 0.0395(11) -0.0073(9) -0.0064(11) -0.0041(11) C9 0.0586(12) 0.0473(12) 0.0402(11) 0.0010(9) -0.0007(9) -0.0073(9) C10 0.0388(10) 0.0463(11) 0.0376(10) 0.0047(8) 0.0001(8) 0.0045(8) C11 0.0450(11) 0.0476(11) 0.0497(12) 0.0033(9) 0.0028(9) 0.0014(9) C12 0.0484(12) 0.0529(13) 0.0755(16) 0.0119(11) 0.0070(11) -0.0020(10) C13 0.0509(13) 0.0897(18) 0.0627(15) 0.0226(13) 0.0168(11) 0.0056(12) C14 0.0609(14) 0.114(2) 0.0425(13) 0.0005(13) 0.0120(11) 0.0042(15) C15 0.0537(13) 0.0812(17) 0.0436(12) -0.0068(11) 0.0062(10) -0.0061(11) C16 0.0375(10) 0.0538(12) 0.0400(10) -0.0083(9) 0.0034(8) -0.0061(8) C17 0.0592(13) 0.0729(15) 0.0406(11) -0.0101(10) 0.0034(10) -0.0092(11) C18 0.0599(14) 0.0815(17) 0.0605(15) -0.0336(13) 0.0097(12) -0.0090(12) C19 0.0593(14) 0.0616(15) 0.0808(18) -0.0235(13) 0.0084(13) -0.0016(11) C20 0.0702(15) 0.0571(15) 0.0701(16) -0.0025(11) 0.0065(12) 0.0042(11) C21 0.0593(13) 0.0546(13) 0.0444(11) -0.0063(9) 0.0061(10) 0.0011(10) C22 0.0501(12) 0.0565(13) 0.0524(12) 0.0018(10) 0.0036(10) 0.0001(10) 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 O2 S1 O3 119.97(10) . . O2 S1 N2 105.52(9) . . O3 S1 N2 107.15(9) . . O2 S1 C22 108.75(11) . . O3 S1 C22 108.25(10) . . N2 S1 C22 106.42(9) . . C3 N1 C1 104.00(15) . . C1 N2 C16 117.43(14) . . C1 N2 S1 115.20(13) . . C16 N2 S1 119.78(11) . . C3 O1 C2 105.83(13) . . C2 C1 N1 111.02(15) . . C2 C1 N2 127.18(17) . . N1 C1 N2 121.79(16) . . C1 C2 O1 105.76(16) . . C1 C2 C10 136.76(17) . . O1 C2 C10 117.47(15) . . N1 C3 O1 113.39(16) . . N1 C3 C4 127.90(18) . . O1 C3 C4 118.72(16) . . C5 C4 C9 119.10(18) . . C5 C4 C3 119.79(17) . . C9 C4 C3 121.10(18) . . C6 C5 C4 120.6(2) . . C6 C5 H5 119.7 . . C4 C5 H5 119.7 . . C5 C6 C7 119.8(2) . . C5 C6 H6 120.1 . . C7 C6 H6 120.1 . . C8 C7 C6 120.0(2) . . C8 C7 H7 120.0 . . C6 C7 H7 120.0 . . C7 C8 C9 120.7(2) . . C7 C8 H8 119.6 . . C9 C8 H8 119.6 . . C8 C9 C4 119.8(2) . . C8 C9 H9 120.1 . . C4 C9 H9 120.1 . . C11 C10 C15 118.15(19) . . C11 C10 C2 121.25(17) . . C15 C10 C2 120.60(18) . . C12 C11 C10 120.6(2) . . C12 C11 H11 119.7 . . C10 C11 H11 119.7 . . C13 C12 C11 120.6(2) . . C13 C12 H12 119.7 . . C11 C12 H12 119.7 . . C12 C13 C14 119.5(2) . . C12 C13 H13 120.2 . . C14 C13 H13 120.2 . . C13 C14 C15 120.6(2) . . C13 C14 H14 119.7 . . C15 C14 H14 119.7 . . C14 C15 C10 120.5(2) . . C14 C15 H15 119.7 . . C10 C15 H15 119.7 . . C21 C16 C17 120.0(2) . . C21 C16 N2 120.14(17) . . C17 C16 N2 119.84(18) . . C16 C17 C18 119.3(2) . . C16 C17 H17 120.4 . . C18 C17 H17 120.4 . . C19 C18 C17 121.0(2) . . C19 C18 H18 119.5 . . C17 C18 H18 119.5 . . C18 C19 C20 119.4(2) . . C18 C19 H19 120.3 . . C20 C19 H19 120.3 . . C19 C20 C21 120.5(2) . . C19 C20 H20 119.7 . . C21 C20 H20 119.7 . . C16 C21 C20 119.9(2) . . C16 C21 H21 120.1 . . C20 C21 H21 120.1 . . S1 C22 H22A 109.5 . . S1 C22 H22B 109.5 . . H22A C22 H22B 109.5 . . S1 C22 H22C 109.5 . . H22A C22 H22C 109.5 . . H22B C22 H22C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 S1 O2 1.4177(16) . S1 O3 1.4247(15) . S1 N2 1.6728(16) . S1 C22 1.750(2) . N1 C3 1.303(2) . N1 C1 1.386(2) . N2 C1 1.428(2) . N2 C16 1.458(3) . O1 C3 1.359(2) . O1 C2 1.382(2) . C1 C2 1.352(3) . C2 C10 1.450(3) . C3 C4 1.452(3) . C4 C5 1.389(3) . C4 C9 1.389(3) . C5 C6 1.380(3) . C5 H5 0.9300 . C6 C7 1.380(3) . C6 H6 0.9300 . C7 C8 1.372(3) . C7 H7 0.9300 . C8 C9 1.384(3) . C8 H8 0.9300 . C9 H9 0.9300 . C10 C11 1.388(3) . C10 C15 1.394(3) . C11 C12 1.381(3) . C11 H11 0.9300 . C12 C13 1.367(3) . C12 H12 0.9300 . C13 C14 1.375(3) . C13 H13 0.9300 . C14 C15 1.376(3) . C14 H14 0.9300 . C15 H15 0.9300 . C16 C21 1.379(3) . C16 C17 1.382(3) . C17 C18 1.383(3) . C17 H17 0.9300 . C18 C19 1.371(4) . C18 H18 0.9300 . C19 C20 1.372(3) . C19 H19 0.9300 . C20 C21 1.382(3) . C20 H20 0.9300 . C21 H21 0.9300 . C22 H22A 0.9600 . C22 H22B 0.9600 . C22 H22C 0.9600 . 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 C22 H22C N1 0.96 2.58 3.160(2) 119.3 . C21 H21 N1 0.93 2.55 3.192(3) 126.8 . C21 H21 N1 0.93 2.55 3.192(3) 126.8 . 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 S1 N2 C1 -44.82(16) . . . . O3 S1 N2 C1 -173.74(14) . . . . C22 S1 N2 C1 70.63(15) . . . . O2 S1 N2 C16 166.32(15) . . . . O3 S1 N2 C16 37.40(17) . . . . C22 S1 N2 C16 -78.23(16) . . . . C3 N1 C1 C2 0.2(2) . . . . C3 N1 C1 N2 -179.76(16) . . . . C16 N2 C1 C2 -98.5(2) . . . . S1 N2 C1 C2 111.85(19) . . . . C16 N2 C1 N1 81.4(2) . . . . S1 N2 C1 N1 -68.2(2) . . . . N1 C1 C2 O1 -0.5(2) . . . . N2 C1 C2 O1 179.45(16) . . . . N1 C1 C2 C10 178.1(2) . . . . N2 C1 C2 C10 -1.9(4) . . . . C3 O1 C2 C1 0.60(19) . . . . C3 O1 C2 C10 -178.34(15) . . . . C1 N1 C3 O1 0.2(2) . . . . C1 N1 C3 C4 179.73(18) . . . . C2 O1 C3 N1 -0.5(2) . . . . C2 O1 C3 C4 179.90(15) . . . . N1 C3 C4 C5 2.7(3) . . . . O1 C3 C4 C5 -177.74(16) . . . . N1 C3 C4 C9 -175.82(19) . . . . O1 C3 C4 C9 3.7(3) . . . . C9 C4 C5 C6 0.4(3) . . . . C3 C4 C5 C6 -178.17(19) . . . . C4 C5 C6 C7 -0.5(3) . . . . C5 C6 C7 C8 0.3(3) . . . . C6 C7 C8 C9 0.0(3) . . . . C7 C8 C9 C4 -0.1(3) . . . . C5 C4 C9 C8 -0.1(3) . . . . C3 C4 C9 C8 178.44(18) . . . . C1 C2 C10 C11 -166.2(2) . . . . O1 C2 C10 C11 12.3(3) . . . . C1 C2 C10 C15 12.9(3) . . . . O1 C2 C10 C15 -168.57(17) . . . . C15 C10 C11 C12 0.8(3) . . . . C2 C10 C11 C12 179.89(18) . . . . C10 C11 C12 C13 -0.8(3) . . . . C11 C12 C13 C14 0.2(3) . . . . C12 C13 C14 C15 0.4(4) . . . . C13 C14 C15 C10 -0.4(4) . . . . C11 C10 C15 C14 -0.1(3) . . . . C2 C10 C15 C14 -179.3(2) . . . . C1 N2 C16 C21 -31.9(3) . . . . S1 N2 C16 C21 116.28(18) . . . . C1 N2 C16 C17 145.36(19) . . . . S1 N2 C16 C17 -66.5(2) . . . . C21 C16 C17 C18 -1.8(3) . . . . N2 C16 C17 C18 -179.10(18) . . . . C16 C17 C18 C19 0.2(3) . . . . C17 C18 C19 C20 1.5(4) . . . . C18 C19 C20 C21 -1.6(4) . . . . C17 C16 C21 C20 1.8(3) . . . . N2 C16 C21 C20 179.02(18) . . . . C19 C20 C21 C16 0.0(3) . . . .