#------------------------------------------------------------------------------ #$Date: 2019-11-17 07:10:30 +0200 (Sun, 17 Nov 2019) $ #$Revision: 228587 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/11/7121121.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_7121121 loop_ _publ_author_name 'Sun, Deli' 'Yin, Kun' 'Zhang, Ronghua' _publ_section_title ; Visible-light-induced multicomponent cascade cycloaddition involving N-propargyl aromatic amines, diaryliodonium salts and sulfur dioxide: rapid access to 3-arylsulfonylquinolines. ; _journal_issue 11 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 1335 _journal_page_last 1338 _journal_paper_doi 10.1039/c7cc09410h _journal_volume 54 _journal_year 2018 _chemical_formula_sum 'C22 H17 N O2 S' _chemical_formula_weight 359.42 _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 _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2017-11-20 deposited with the CCDC. 2018-01-09 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 96.831(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.3596(8) _cell_length_b 10.4885(12) _cell_length_c 23.677(3) _cell_measurement_reflns_used 9928 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 27.52 _cell_measurement_theta_min 2.79 _cell_volume 1814.7(4) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX3' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-III CMOS' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_unetI/netI 0.0267 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_number 23471 _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 27.100 _diffrn_reflns_theta_min 3.103 _exptl_absorpt_coefficient_mu 0.194 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.316 _exptl_crystal_description sheet _exptl_crystal_F_000 752 _exptl_crystal_size_max 0.450 _exptl_crystal_size_mid 0.060 _exptl_crystal_size_min 0.050 _exptl_transmission_factor_max 0.7456 _exptl_transmission_factor_min 0.6761 _refine_diff_density_max 0.226 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.044 _refine_ls_extinction_coef 0.0196(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2016/6 (Sheldrick 2016)' _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 237 _refine_ls_number_reflns 4014 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.087 _refine_ls_R_factor_all 0.0709 _refine_ls_R_factor_gt 0.0498 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0362P)^2^+0.9536P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1055 _refine_ls_wR_factor_ref 0.1170 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3072 _reflns_number_total 4014 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7cc09410h2.cif _cod_data_source_block mo_171115a_a _cod_depositor_comments 'Adding full bibliography for 7121121.cif.' _cod_database_code 7121121 _shelx_shelxl_version_number 2016/6 _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 0.918 _shelx_estimated_absorpt_t_max 0.990 _shelx_res_file ; TITL mo_171115a_a.res in P2(1)/c mo_171115a_a.res created by SHELXL-2016/6 at 16:09:51 on 20-Nov-2017 REM Old TITL mo_171115a in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.176, Rweak 0.010, Alpha 0.035, Orientation as input REM Formula found by SHELXT: C23 O2 S CELL 0.71073 7.3596 10.4885 23.6766 90.000 96.831 90.000 ZERR 4.000 0.0008 0.0012 0.0029 0.000 0.004 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H N O S UNIT 88 68 4 8 4 TEMP 25.230 L.S. 10 BOND $H shel 7.23 0.78 LIST 4 acta conf size 0.05 0.06 0.45 FMAP 2 PLAN 20 WGHT 0.036200 0.953600 EXTI 0.019565 FVAR 0.59042 S1 5 0.381727 0.674831 0.691777 11.00000 0.04084 0.05586 = 0.04836 0.01614 0.00309 0.00176 O1 4 0.567329 0.718570 0.695164 11.00000 0.03691 0.07871 = 0.06863 0.01657 -0.00034 -0.00007 O2 4 0.337617 0.580799 0.732242 11.00000 0.06446 0.07468 = 0.06262 0.03479 0.00974 0.00515 N1 3 0.257943 0.407268 0.575162 11.00000 0.06521 0.03246 = 0.09411 0.00175 0.01791 0.00147 C1 1 0.249403 0.472009 0.524863 11.00000 0.04383 0.03654 = 0.08088 -0.01005 0.01347 0.00325 C2 1 0.216292 0.401654 0.474060 11.00000 0.06076 0.04396 = 0.10187 -0.02511 0.01170 -0.00152 AFIX 43 H2 2 0.199932 0.313860 0.475641 11.00000 -1.20000 AFIX 0 C3 1 0.208034 0.460291 0.423057 11.00000 0.06267 0.06863 = 0.08513 -0.04020 0.00454 -0.00087 AFIX 43 H3 2 0.188290 0.411490 0.390103 11.00000 -1.20000 AFIX 0 C4 1 0.228487 0.593423 0.418314 11.00000 0.05708 0.07300 = 0.05996 -0.01942 0.00583 -0.00162 C5 1 0.260828 0.663425 0.467357 11.00000 0.05798 0.04686 = 0.05410 -0.00787 0.00795 -0.00576 AFIX 43 H5 2 0.275453 0.751235 0.464838 11.00000 -1.20000 AFIX 0 C6 1 0.272561 0.605993 0.521579 11.00000 0.03997 0.03650 = 0.05817 -0.00540 0.00996 -0.00126 C7 1 0.215199 0.655713 0.360771 11.00000 0.12104 0.10794 = 0.05366 -0.01642 0.00139 -0.00945 AFIX 137 H7A 2 0.251287 0.596000 0.333466 11.00000 -1.50000 H7B 2 0.294513 0.728631 0.362522 11.00000 -1.50000 H7C 2 0.091314 0.682279 0.349586 11.00000 -1.50000 AFIX 0 C8 1 0.311643 0.675277 0.573184 11.00000 0.03906 0.03188 = 0.05097 0.00144 0.01029 0.00036 C9 1 0.337991 0.816901 0.571387 11.00000 0.05492 0.03125 = 0.03471 0.00168 0.00709 0.00004 C10 1 0.187951 0.896506 0.559773 11.00000 0.06337 0.04228 = 0.04709 0.00082 -0.00459 0.00494 AFIX 43 H10 2 0.071099 0.862105 0.552291 11.00000 -1.20000 AFIX 0 C11 1 0.212394 1.027544 0.559331 11.00000 0.08985 0.04297 = 0.05434 0.00460 -0.00243 0.01824 AFIX 43 H11 2 0.111522 1.080949 0.551868 11.00000 -1.20000 AFIX 0 C12 1 0.384784 1.078952 0.569855 11.00000 0.10287 0.03331 = 0.06090 0.00252 0.00806 -0.00516 AFIX 43 H12 2 0.400394 1.166944 0.569932 11.00000 -1.20000 AFIX 0 C13 1 0.533507 1.000403 0.580227 11.00000 0.07682 0.04236 = 0.06562 0.00114 0.01385 -0.01280 AFIX 43 H13 2 0.650427 1.035095 0.586678 11.00000 -1.20000 AFIX 0 C14 1 0.510442 0.869645 0.581142 11.00000 0.05611 0.03962 = 0.05390 0.00256 0.01492 -0.00272 AFIX 43 H14 2 0.612059 0.816847 0.588395 11.00000 -1.20000 AFIX 0 C15 1 0.321530 0.607231 0.623266 11.00000 0.04110 0.03655 = 0.05807 0.00775 0.01133 0.00370 C16 1 0.291623 0.473645 0.621870 11.00000 0.06042 0.03835 = 0.07922 0.01577 0.01627 0.00325 AFIX 43 H16 2 0.296295 0.430665 0.656368 11.00000 -1.20000 AFIX 0 C17 1 0.236985 0.806556 0.696697 11.00000 0.03896 0.05370 = 0.03178 0.00165 0.00132 -0.00304 C18 1 0.310931 0.926729 0.703621 11.00000 0.04372 0.06282 = 0.04302 -0.00680 0.00267 -0.01055 AFIX 43 H18 2 0.436634 0.938823 0.705266 11.00000 -1.20000 AFIX 0 C19 1 0.196043 1.028867 0.708081 11.00000 0.06662 0.05541 = 0.05880 -0.01559 0.00890 -0.00915 AFIX 43 H19 2 0.244249 1.110659 0.712804 11.00000 -1.20000 AFIX 0 C20 1 0.010427 1.010435 0.705580 11.00000 0.06131 0.06585 = 0.06159 -0.01490 0.01230 0.00902 AFIX 43 H20 2 -0.066504 1.080076 0.707967 11.00000 -1.20000 AFIX 0 C21 1 -0.062622 0.889503 0.699562 11.00000 0.04109 0.07332 = 0.06630 -0.00751 0.00913 0.00102 AFIX 43 H21 2 -0.188244 0.877734 0.698453 11.00000 -1.20000 AFIX 0 C22 1 0.049767 0.786424 0.695202 11.00000 0.04415 0.05851 = 0.04918 -0.00122 0.00381 -0.00962 AFIX 43 H22 2 0.001501 0.704517 0.691315 11.00000 -1.20000 AFIX 0 HKLF 4 REM mo_171115a_a.res in P2(1)/c REM R1 = 0.0498 for 3072 Fo > 4sig(Fo) and 0.0709 for all 4014 data REM 237 parameters refined using 0 restraints END WGHT 0.0362 0.9536 REM Highest difference peak 0.226, deepest hole -0.316, 1-sigma level 0.044 Q1 1 0.3063 0.5323 0.5260 11.00000 0.05 0.23 Q2 1 0.2545 0.8417 0.5707 11.00000 0.05 0.21 Q3 1 0.3220 0.7468 0.5756 11.00000 0.05 0.21 Q4 1 0.3396 0.5487 0.6205 11.00000 0.05 0.21 Q5 1 0.2882 0.7468 0.6908 11.00000 0.05 0.20 Q6 1 0.3123 0.6392 0.5481 11.00000 0.05 0.20 Q7 1 0.3608 0.6236 0.6521 11.00000 0.05 0.20 Q8 1 0.1254 0.5833 0.3368 11.00000 0.05 0.19 Q9 1 0.3440 0.6450 0.6008 11.00000 0.05 0.18 Q10 1 0.2541 0.5431 0.7001 11.00000 0.05 0.17 Q11 1 0.2246 0.8285 0.4306 11.00000 0.05 0.17 Q12 1 0.2273 0.4428 0.5477 11.00000 0.05 0.17 Q13 1 0.1499 0.4271 0.4489 11.00000 0.05 0.16 Q14 1 0.1963 0.5432 0.4242 11.00000 0.05 0.16 Q15 1 0.2146 0.7807 0.3587 11.00000 0.05 0.15 Q16 1 0.1584 0.7924 0.7054 11.00000 0.05 0.15 Q17 1 0.0031 1.0401 0.5609 11.00000 0.05 0.15 Q18 1 0.3107 0.4215 0.6950 11.00000 0.05 0.15 Q19 1 0.2227 0.5556 0.5256 11.00000 0.05 0.15 Q20 1 0.1527 0.7435 0.3625 11.00000 0.05 0.15 ; _shelx_res_checksum 882 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 S1 S 0.38173(7) 0.67483(5) 0.69178(2) 0.04853(17) Uani 1 1 d . . O1 O 0.56733(18) 0.71857(16) 0.69516(7) 0.0620(4) Uani 1 1 d . . O2 O 0.3376(2) 0.58080(16) 0.73224(7) 0.0671(5) Uani 1 1 d . . N1 N 0.2579(3) 0.40727(17) 0.57516(10) 0.0632(5) Uani 1 1 d . . C1 C 0.2494(3) 0.47201(19) 0.52486(10) 0.0533(5) Uani 1 1 d . . C2 C 0.2163(3) 0.4017(2) 0.47406(13) 0.0687(7) Uani 1 1 d . . H2 H 0.199932 0.313860 0.475641 0.082 Uiso 1 1 calc R U C3 C 0.2080(3) 0.4603(3) 0.42306(13) 0.0725(8) Uani 1 1 d . . H3 H 0.188290 0.411490 0.390103 0.087 Uiso 1 1 calc R U C4 C 0.2285(3) 0.5934(3) 0.41831(10) 0.0634(6) Uani 1 1 d . . C5 C 0.2608(3) 0.6634(2) 0.46736(9) 0.0529(5) Uani 1 1 d . . H5 H 0.275453 0.751235 0.464838 0.063 Uiso 1 1 calc R U C6 C 0.2726(3) 0.60599(18) 0.52158(9) 0.0445(5) Uani 1 1 d . . C7 C 0.2152(5) 0.6557(3) 0.36077(11) 0.0949(10) Uani 1 1 d . . H7A H 0.251287 0.596000 0.333466 0.142 Uiso 1 1 calc R U H7B H 0.294513 0.728631 0.362522 0.142 Uiso 1 1 calc R U H7C H 0.091314 0.682279 0.349586 0.142 Uiso 1 1 calc R U C8 C 0.3116(2) 0.67528(17) 0.57318(8) 0.0402(4) Uani 1 1 d . . C9 C 0.3380(3) 0.81690(17) 0.57139(7) 0.0402(4) Uani 1 1 d . . C10 C 0.1880(3) 0.89651(19) 0.55977(8) 0.0518(5) Uani 1 1 d . . H10 H 0.071099 0.862105 0.552291 0.062 Uiso 1 1 calc R U C11 C 0.2124(4) 1.0275(2) 0.55933(10) 0.0633(6) Uani 1 1 d . . H11 H 0.111522 1.080949 0.551868 0.076 Uiso 1 1 calc R U C12 C 0.3848(4) 1.0790(2) 0.56986(10) 0.0658(7) Uani 1 1 d . . H12 H 0.400394 1.166944 0.569932 0.079 Uiso 1 1 calc R U C13 C 0.5335(4) 1.0004(2) 0.58023(10) 0.0612(6) Uani 1 1 d . . H13 H 0.650427 1.035095 0.586678 0.073 Uiso 1 1 calc R U C14 C 0.5104(3) 0.86965(19) 0.58114(9) 0.0492(5) Uani 1 1 d . . H14 H 0.612059 0.816847 0.588395 0.059 Uiso 1 1 calc R U C15 C 0.3215(3) 0.60723(18) 0.62327(9) 0.0448(5) Uani 1 1 d . . C16 C 0.2916(3) 0.4736(2) 0.62187(11) 0.0587(6) Uani 1 1 d . . H16 H 0.296295 0.430665 0.656368 0.070 Uiso 1 1 calc R U C17 C 0.2370(2) 0.80656(19) 0.69670(7) 0.0417(4) Uani 1 1 d . . C18 C 0.3109(3) 0.9267(2) 0.70362(8) 0.0501(5) Uani 1 1 d . . H18 H 0.436634 0.938823 0.705266 0.060 Uiso 1 1 calc R U C19 C 0.1960(3) 1.0289(2) 0.70808(10) 0.0602(6) Uani 1 1 d . . H19 H 0.244249 1.110659 0.712804 0.072 Uiso 1 1 calc R U C20 C 0.0104(3) 1.0104(2) 0.70558(10) 0.0625(6) Uani 1 1 d . . H20 H -0.066504 1.080076 0.707967 0.075 Uiso 1 1 calc R U C21 C -0.0626(3) 0.8895(2) 0.69956(10) 0.0600(6) Uani 1 1 d . . H21 H -0.188244 0.877734 0.698453 0.072 Uiso 1 1 calc R U C22 C 0.0498(3) 0.7864(2) 0.69520(9) 0.0508(5) Uani 1 1 d . . H22 H 0.001501 0.704517 0.691315 0.061 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 0.0408(3) 0.0559(3) 0.0484(3) 0.0161(2) 0.0031(2) 0.0018(2) O1 0.0369(7) 0.0787(11) 0.0686(10) 0.0166(8) -0.0003(7) -0.0001(7) O2 0.0645(10) 0.0747(11) 0.0626(10) 0.0348(8) 0.0097(8) 0.0052(8) N1 0.0652(12) 0.0325(9) 0.0941(16) 0.0018(10) 0.0179(11) 0.0015(8) C1 0.0438(11) 0.0365(11) 0.0809(16) -0.0101(10) 0.0135(10) 0.0032(9) C2 0.0608(15) 0.0440(13) 0.102(2) -0.0251(13) 0.0117(14) -0.0015(11) C3 0.0627(15) 0.0686(17) 0.0851(19) -0.0402(15) 0.0045(13) -0.0009(12) C4 0.0571(13) 0.0730(16) 0.0600(14) -0.0194(12) 0.0058(11) -0.0016(12) C5 0.0580(12) 0.0469(12) 0.0541(12) -0.0079(10) 0.0079(10) -0.0058(10) C6 0.0400(10) 0.0365(10) 0.0582(12) -0.0054(9) 0.0100(9) -0.0013(8) C7 0.121(3) 0.108(2) 0.0537(15) -0.0164(16) 0.0014(15) -0.009(2) C8 0.0391(9) 0.0319(9) 0.0510(11) 0.0014(8) 0.0103(8) 0.0004(8) C9 0.0549(11) 0.0312(9) 0.0347(9) 0.0017(7) 0.0071(8) 0.0000(8) C10 0.0634(13) 0.0423(11) 0.0471(12) 0.0008(9) -0.0046(9) 0.0049(10) C11 0.0898(18) 0.0430(12) 0.0543(13) 0.0046(10) -0.0024(12) 0.0182(12) C12 0.103(2) 0.0333(11) 0.0609(14) 0.0025(10) 0.0081(13) -0.0052(12) C13 0.0768(16) 0.0424(12) 0.0656(14) 0.0011(10) 0.0139(12) -0.0128(11) C14 0.0561(12) 0.0396(10) 0.0539(12) 0.0026(9) 0.0149(9) -0.0027(9) C15 0.0411(10) 0.0365(10) 0.0581(12) 0.0078(9) 0.0113(9) 0.0037(8) C16 0.0604(14) 0.0384(11) 0.0792(16) 0.0158(11) 0.0163(12) 0.0033(10) C17 0.0390(10) 0.0537(11) 0.0318(9) 0.0017(8) 0.0013(7) -0.0030(8) C18 0.0437(11) 0.0628(13) 0.0430(11) -0.0068(9) 0.0027(8) -0.0106(10) C19 0.0666(15) 0.0554(13) 0.0588(14) -0.0156(11) 0.0089(11) -0.0091(11) C20 0.0613(14) 0.0658(15) 0.0616(14) -0.0149(12) 0.0123(11) 0.0090(12) C21 0.0411(11) 0.0733(16) 0.0663(14) -0.0075(12) 0.0091(10) 0.0010(11) C22 0.0441(11) 0.0585(13) 0.0492(12) -0.0012(10) 0.0038(9) -0.0096(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 O1 S1 O2 118.09(9) O1 S1 C17 109.01(10) O2 S1 C17 107.96(9) O1 S1 C15 108.12(9) O2 S1 C15 106.43(10) C17 S1 C15 106.67(9) C16 N1 C1 117.26(18) N1 C1 C2 118.0(2) N1 C1 C6 123.1(2) C2 C1 C6 118.8(2) C3 C2 C1 120.7(2) C3 C2 H2 119.7 C1 C2 H2 119.7 C2 C3 C4 121.9(2) C2 C3 H3 119.1 C4 C3 H3 119.1 C5 C4 C3 118.2(2) C5 C4 C7 121.4(2) C3 C4 C7 120.4(2) C4 C5 C6 121.8(2) C4 C5 H5 119.1 C6 C5 H5 119.1 C5 C6 C1 118.54(19) C5 C6 C8 123.23(18) C1 C6 C8 118.21(19) C4 C7 H7A 109.5 C4 C7 H7B 109.5 H7A C7 H7B 109.5 C4 C7 H7C 109.5 H7A C7 H7C 109.5 H7B C7 H7C 109.5 C15 C8 C6 117.35(17) C15 C8 C9 122.93(17) C6 C8 C9 119.72(17) C14 C9 C10 119.18(18) C14 C9 C8 120.83(17) C10 C9 C8 120.00(18) C9 C10 C11 119.9(2) C9 C10 H10 120.1 C11 C10 H10 120.1 C12 C11 C10 120.4(2) C12 C11 H11 119.8 C10 C11 H11 119.8 C13 C12 C11 119.9(2) C13 C12 H12 120.1 C11 C12 H12 120.1 C12 C13 C14 120.2(2) C12 C13 H13 119.9 C14 C13 H13 119.9 C9 C14 C13 120.5(2) C9 C14 H14 119.7 C13 C14 H14 119.7 C8 C15 C16 120.0(2) C8 C15 S1 124.09(15) C16 C15 S1 115.88(16) N1 C16 C15 124.1(2) N1 C16 H16 118.0 C15 C16 H16 118.0 C18 C17 C22 121.28(19) C18 C17 S1 119.62(15) C22 C17 S1 119.06(16) C17 C18 C19 118.98(19) C17 C18 H18 120.5 C19 C18 H18 120.5 C20 C19 C18 120.3(2) C20 C19 H19 119.9 C18 C19 H19 119.9 C19 C20 C21 120.5(2) C19 C20 H20 119.8 C21 C20 H20 119.8 C22 C21 C20 120.1(2) C22 C21 H21 120.0 C20 C21 H21 120.0 C21 C22 C17 118.9(2) C21 C22 H22 120.6 C17 C22 H22 120.6 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 O1 1.4341(15) S1 O2 1.4387(15) S1 C17 1.757(2) S1 C15 1.777(2) N1 C16 1.305(3) N1 C1 1.366(3) C1 C2 1.407(3) C1 C6 1.419(3) C2 C3 1.350(4) C2 H2 0.9300 C3 C4 1.410(4) C3 H3 0.9300 C4 C5 1.371(3) C4 C7 1.504(4) C5 C6 1.411(3) C5 H5 0.9300 C6 C8 1.421(3) C7 H7A 0.9600 C7 H7B 0.9600 C7 H7C 0.9600 C8 C15 1.378(3) C8 C9 1.499(2) C9 C14 1.379(3) C9 C10 1.386(3) C10 C11 1.386(3) C10 H10 0.9300 C11 C12 1.374(4) C11 H11 0.9300 C12 C13 1.369(3) C12 H12 0.9300 C13 C14 1.382(3) C13 H13 0.9300 C14 H14 0.9300 C15 C16 1.418(3) C16 H16 0.9300 C17 C18 1.375(3) C17 C22 1.390(3) C18 C19 1.377(3) C18 H18 0.9300 C19 C20 1.374(3) C19 H19 0.9300 C20 C21 1.378(3) C20 H20 0.9300 C21 C22 1.373(3) C21 H21 0.9300 C22 H22 0.9300 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 C16 N1 C1 C2 178.9(2) C16 N1 C1 C6 -0.9(3) N1 C1 C2 C3 -179.4(2) C6 C1 C2 C3 0.5(3) C1 C2 C3 C4 -1.2(4) C2 C3 C4 C5 1.2(4) C2 C3 C4 C7 -178.9(2) C3 C4 C5 C6 -0.5(3) C7 C4 C5 C6 179.6(2) C4 C5 C6 C1 -0.2(3) C4 C5 C6 C8 177.95(19) N1 C1 C6 C5 -179.91(19) C2 C1 C6 C5 0.2(3) N1 C1 C6 C8 1.8(3) C2 C1 C6 C8 -178.05(18) C5 C6 C8 C15 -179.17(18) C1 C6 C8 C15 -1.0(3) C5 C6 C8 C9 1.5(3) C1 C6 C8 C9 179.67(17) C15 C8 C9 C14 76.5(2) C6 C8 C9 C14 -104.2(2) C15 C8 C9 C10 -103.5(2) C6 C8 C9 C10 75.7(2) C14 C9 C10 C11 -1.4(3) C8 C9 C10 C11 178.63(19) C9 C10 C11 C12 0.6(3) C10 C11 C12 C13 0.7(4) C11 C12 C13 C14 -1.2(4) C10 C9 C14 C13 1.0(3) C8 C9 C14 C13 -179.06(19) C12 C13 C14 C9 0.3(3) C6 C8 C15 C16 -0.5(3) C9 C8 C15 C16 178.76(18) C6 C8 C15 S1 176.21(14) C9 C8 C15 S1 -4.5(3) O1 S1 C15 C8 -64.46(18) O2 S1 C15 C8 167.73(16) C17 S1 C15 C8 52.65(18) O1 S1 C15 C16 112.39(16) O2 S1 C15 C16 -15.41(18) C17 S1 C15 C16 -130.49(16) C1 N1 C16 C15 -0.8(3) C8 C15 C16 N1 1.5(3) S1 C15 C16 N1 -175.48(18) O1 S1 C17 C18 -1.00(18) O2 S1 C17 C18 128.44(17) C15 S1 C17 C18 -117.52(16) O1 S1 C17 C22 -179.08(15) O2 S1 C17 C22 -49.65(18) C15 S1 C17 C22 64.39(17) C22 C17 C18 C19 -1.2(3) S1 C17 C18 C19 -179.25(16) C17 C18 C19 C20 0.0(3) C18 C19 C20 C21 1.1(4) C19 C20 C21 C22 -0.9(4) C20 C21 C22 C17 -0.3(3) C18 C17 C22 C21 1.4(3) S1 C17 C22 C21 179.43(16)