#------------------------------------------------------------------------------ #$Date: 2019-10-12 05:39:46 +0300 (Sat, 12 Oct 2019) $ #$Revision: 219311 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/71/7157148.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_7157148 loop_ _publ_author_name 'Zbieg, Jason Robert' 'Li, Jun' 'Wang, Xiaojing' 'Liang, Jun' 'Ortwine, Daniel F.' 'DiPasquale, Antonio' 'Liu, Yanzhou' 'Luo, Lennon Shao-Xiong' 'Lambrecht, Michael John' _publ_section_title ; cis-Selective Synthesis of 1,3-Disubstituted Tetrahydro-\b-Carbolines from N-Sulfonyl N,S-Acetals ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/C9OB01796H _journal_year 2019 _chemical_absolute_configuration ad _chemical_formula_sum 'C23 H26 N2 O3 S' _chemical_formula_weight 410.52 _chemical_name_systematic 14 _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 9.2149(3) _cell_length_b 11.3488(4) _cell_length_c 19.7251(7) _cell_measurement_reflns_used 9888 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 25.33 _cell_measurement_theta_min 2.74 _cell_volume 2062.81(12) _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 1.000 _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 0.0450 _diffrn_reflns_av_unetI/netI 0.0227 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_refln_scan_rate 10 _diffrn_refln_scan_width 1.0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 42376 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 25.367 _diffrn_reflns_theta_min 2.065 _diffrn_source 'fine focus sealed tube' _exptl_absorpt_coefficient_mu 0.184 _exptl_absorpt_correction_T_max 0.928 _exptl_absorpt_correction_T_min 0.842 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.322 _exptl_crystal_description plate _exptl_crystal_F_000 872 _exptl_crystal_size_max 0.080 _exptl_crystal_size_mid 0.080 _exptl_crystal_size_min 0.040 _refine_diff_density_max 0.377 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.048 _refine_ls_abs_structure_details ; Flack x determined using 1494 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.03(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 265 _refine_ls_number_reflns 3784 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.063 _refine_ls_R_factor_all 0.0364 _refine_ls_R_factor_gt 0.0342 _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^)+(0.0474P)^2^+0.6579P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0826 _refine_ls_wR_factor_ref 0.0843 _reflns_Friedel_coverage 0.743 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 1.000 _reflns_number_gt 3597 _reflns_number_total 3784 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ob01796h2.cif _cod_data_source_block 14 _cod_database_code 7157148 _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 0.985 _shelx_estimated_absorpt_t_max 0.993 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL gene708_0m_a.res in P2(1)2(1)2(1) CELL 0.71073 9.2149 11.3488 19.7251 90.000 90.000 90.000 ZERR 4.00 0.0003 0.0004 0.0007 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 92 104 8 12 4 MERG 2 FMAP 2 PLAN 20 SIZE 0.040 0.080 0.080 ACTA 50.00 BOND $H LIST 4 WPDB -2 L.S. 10 TEMP -173.00 WGHT 0.047400 0.657900 FVAR 0.15014 C1 1 0.314346 0.333814 0.756101 11.00000 0.01667 0.01398 = 0.02096 -0.00007 -0.00423 -0.00113 AFIX 13 H1 2 0.381208 0.265452 0.762991 11.00000 -1.20000 AFIX 0 C2 1 0.246609 0.323427 0.687503 11.00000 0.01402 0.01707 = 0.02118 -0.00180 -0.00010 0.00009 C3 1 0.118841 0.245261 0.601987 11.00000 0.01623 0.02310 = 0.01951 -0.00107 0.00067 0.00247 C4 1 0.037626 0.172920 0.559532 11.00000 0.02748 0.02370 = 0.02528 -0.00408 -0.00149 0.00138 AFIX 43 H4 2 0.022080 0.092200 0.570019 11.00000 -1.20000 AFIX 0 C5 1 -0.019859 0.223217 0.501229 11.00000 0.02331 0.03886 = 0.02207 -0.01013 -0.00419 0.00336 AFIX 43 H5 2 -0.076902 0.176174 0.471617 11.00000 -1.20000 AFIX 0 C6 1 0.004336 0.341237 0.485220 11.00000 0.02465 0.04213 = 0.02200 0.00338 -0.00380 0.00763 AFIX 43 H6 2 -0.034163 0.372698 0.444373 11.00000 -1.20000 AFIX 0 C7 1 0.084001 0.413430 0.528214 11.00000 0.02335 0.02808 = 0.02268 0.00508 0.00059 0.00334 AFIX 43 H7 2 0.099312 0.494004 0.517290 11.00000 -1.20000 AFIX 0 C8 1 0.141264 0.365715 0.587772 11.00000 0.01448 0.02358 = 0.02046 0.00090 0.00316 0.00182 C9 1 0.222670 0.413870 0.643752 11.00000 0.01385 0.02111 = 0.02180 0.00109 0.00158 0.00107 C10 1 0.277017 0.536959 0.655296 11.00000 0.02243 0.01885 = 0.03063 0.00453 -0.00486 -0.00093 AFIX 23 H10A 2 0.197659 0.593602 0.646212 11.00000 -1.20000 H10B 2 0.356902 0.553778 0.623161 11.00000 -1.20000 AFIX 0 C11 1 0.332073 0.554122 0.728490 11.00000 0.01816 0.01364 = 0.03103 0.00213 -0.00163 0.00048 AFIX 13 H11 2 0.408747 0.616411 0.726812 11.00000 -1.20000 AFIX 0 C12 1 0.213749 0.598812 0.775908 11.00000 0.02543 0.01915 = 0.03977 -0.00082 0.00464 0.00289 AFIX 137 H12A 2 0.126204 0.550803 0.770184 11.00000 -1.50000 H12B 2 0.191560 0.681152 0.765111 11.00000 -1.50000 H12C 2 0.247369 0.593227 0.822934 11.00000 -1.50000 AFIX 0 C13 1 0.614408 0.401649 0.660647 11.00000 0.02430 0.02468 = 0.02304 -0.00141 0.00058 0.00134 AFIX 13 H13 2 0.560248 0.334046 0.640223 11.00000 -1.20000 AFIX 0 C14 1 0.768582 0.417730 0.636967 11.00000 0.02563 0.04084 = 0.02858 0.00312 0.00684 0.00366 AFIX 23 H14A 2 0.840196 0.447928 0.670101 11.00000 -1.20000 H14B 2 0.807546 0.360116 0.603969 11.00000 -1.20000 AFIX 0 C15 1 0.653130 0.500142 0.613183 11.00000 0.03300 0.03737 = 0.02842 0.00740 0.00467 -0.00208 AFIX 23 H15A 2 0.620901 0.493519 0.565457 11.00000 -1.20000 H15B 2 0.653543 0.581309 0.631572 11.00000 -1.20000 AFIX 0 C16 1 0.202445 0.334120 0.812875 11.00000 0.01903 0.01477 = 0.02134 0.00114 -0.00208 -0.00074 C17 1 0.055126 0.333529 0.798120 11.00000 0.02126 0.02137 = 0.01935 0.00103 -0.00298 -0.00275 AFIX 43 H17 2 0.026128 0.326869 0.752061 11.00000 -1.20000 AFIX 0 C18 1 -0.051807 0.342198 0.847408 11.00000 0.01744 0.02125 = 0.02868 0.00108 -0.00069 -0.00117 AFIX 43 H18 2 -0.151680 0.342273 0.835465 11.00000 -1.20000 AFIX 0 C19 1 -0.008825 0.350731 0.914445 11.00000 0.02164 0.01787 = 0.02338 0.00017 0.00410 -0.00171 C20 1 0.137435 0.347473 0.931429 11.00000 0.02533 0.02126 = 0.01867 -0.00057 -0.00375 -0.00115 AFIX 43 H20 2 0.164864 0.351764 0.977789 11.00000 -1.20000 AFIX 0 C21 1 0.244341 0.338091 0.882188 11.00000 0.02112 0.01683 = 0.02186 -0.00032 -0.00273 -0.00025 C22 1 0.400440 0.335983 0.903692 11.00000 0.01969 0.02730 = 0.02055 -0.00046 -0.00141 0.00008 AFIX 137 H22A 2 0.443523 0.413944 0.896528 11.00000 -1.50000 H22B 2 0.453199 0.277403 0.876767 11.00000 -1.50000 H22C 2 0.406592 0.315222 0.951832 11.00000 -1.50000 AFIX 0 C23 1 -0.252829 0.379303 0.951068 11.00000 0.01852 0.03770 = 0.02876 -0.00141 0.00304 -0.00028 AFIX 137 H23A 2 -0.264059 0.449271 0.922427 11.00000 -1.50000 H23B 2 -0.309702 0.389195 0.992662 11.00000 -1.50000 H23C 2 -0.287337 0.309707 0.926468 11.00000 -1.50000 AFIX 0 N1 3 0.402276 0.444989 0.756506 11.00000 0.01485 0.01439 = 0.02188 -0.00002 -0.00225 -0.00111 N2 3 0.184831 0.220735 0.663056 11.00000 0.02295 0.01461 = 0.02021 0.00036 -0.00424 -0.00027 AFIX 43 H2 2 0.187277 0.151502 0.683114 11.00000 -1.20000 AFIX 0 O1 4 0.621472 0.329926 0.783987 11.00000 0.01821 0.02308 = 0.02580 0.00102 -0.00395 0.00224 O2 4 0.642370 0.543047 0.762781 11.00000 0.01830 0.02305 = 0.03578 -0.00609 -0.00362 -0.00165 O3 4 -0.103265 0.364341 0.968044 11.00000 0.02134 0.03735 = 0.02304 0.00037 0.00147 0.00163 S1 5 0.577265 0.431604 0.745999 11.00000 0.01487 0.01736 = 0.02056 -0.00175 -0.00107 -0.00030 HKLF 4 REM gene708_0m_a.res in P2(1)2(1)2(1) REM R1 = 0.0342 for 3597 Fo > 4sig(Fo) and 0.0364 for all 3784 data REM 265 parameters refined using 0 restraints END WGHT 0.0470 0.6696 REM Highest difference peak 0.377, deepest hole -0.230, 1-sigma level 0.048 Q1 1 0.5947 0.4255 0.6992 11.00000 0.05 0.38 Q2 1 0.2310 0.3214 0.8434 11.00000 0.05 0.20 Q3 1 0.6084 0.4663 0.6463 11.00000 0.05 0.20 Q4 1 0.0145 0.3162 0.8225 11.00000 0.05 0.19 Q5 1 0.2340 0.4748 0.6496 11.00000 0.05 0.18 Q6 1 0.2389 0.3327 0.7883 11.00000 0.05 0.18 Q7 1 0.1973 0.3834 0.6001 11.00000 0.05 0.18 Q8 1 0.1556 0.3231 0.8144 11.00000 0.05 0.17 Q9 1 0.1125 0.2037 0.5705 11.00000 0.05 0.17 Q10 1 0.1982 0.3937 0.6701 11.00000 0.05 0.17 Q11 1 -0.0169 0.3296 0.8756 11.00000 0.05 0.17 Q12 1 0.3204 0.3064 0.7087 11.00000 0.05 0.17 Q13 1 -0.2821 0.3665 0.9078 11.00000 0.05 0.17 Q14 1 0.2316 0.3919 0.8488 11.00000 0.05 0.17 Q15 1 0.6077 0.3324 0.7452 11.00000 0.05 0.16 Q16 1 0.7207 0.3950 0.6596 11.00000 0.05 0.16 Q17 1 0.4630 0.4344 0.7486 11.00000 0.05 0.16 Q18 1 0.1017 0.3032 0.6003 11.00000 0.05 0.16 Q19 1 0.1755 0.2216 0.6247 11.00000 0.05 0.16 Q20 1 0.3072 0.5533 0.6917 11.00000 0.05 0.16 ; _shelx_res_checksum 85783 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 0.3143(3) 0.3338(2) 0.75610(13) 0.0172(5) Uani 1 1 d . . H1 H 0.3812 0.2655 0.7630 0.021 Uiso 1 1 calc R U C2 C 0.2466(3) 0.3234(2) 0.68750(13) 0.0174(5) Uani 1 1 d . . C3 C 0.1188(3) 0.2453(2) 0.60199(12) 0.0196(6) Uani 1 1 d . . C4 C 0.0376(3) 0.1729(2) 0.55953(13) 0.0255(6) Uani 1 1 d . . H4 H 0.0221 0.0922 0.5700 0.031 Uiso 1 1 calc R U C5 C -0.0199(3) 0.2232(3) 0.50123(14) 0.0281(6) Uani 1 1 d . . H5 H -0.0769 0.1762 0.4716 0.034 Uiso 1 1 calc R U C6 C 0.0043(3) 0.3412(3) 0.48522(14) 0.0296(7) Uani 1 1 d . . H6 H -0.0342 0.3727 0.4444 0.036 Uiso 1 1 calc R U C7 C 0.0840(3) 0.4134(2) 0.52821(13) 0.0247(6) Uani 1 1 d . . H7 H 0.0993 0.4940 0.5173 0.030 Uiso 1 1 calc R U C8 C 0.1413(3) 0.3657(2) 0.58777(13) 0.0195(5) Uani 1 1 d . . C9 C 0.2227(3) 0.4139(2) 0.64375(12) 0.0189(5) Uani 1 1 d . . C10 C 0.2770(3) 0.5370(2) 0.65530(14) 0.0240(6) Uani 1 1 d . . H10A H 0.1977 0.5936 0.6462 0.029 Uiso 1 1 calc R U H10B H 0.3569 0.5538 0.6232 0.029 Uiso 1 1 calc R U C11 C 0.3321(3) 0.5541(2) 0.72849(13) 0.0209(6) Uani 1 1 d . . H11 H 0.4087 0.6164 0.7268 0.025 Uiso 1 1 calc R U C12 C 0.2137(3) 0.5988(2) 0.77591(15) 0.0281(6) Uani 1 1 d . . H12A H 0.1262 0.5508 0.7702 0.042 Uiso 1 1 calc R U H12B H 0.1916 0.6812 0.7651 0.042 Uiso 1 1 calc R U H12C H 0.2474 0.5932 0.8229 0.042 Uiso 1 1 calc R U C13 C 0.6144(3) 0.4016(2) 0.66065(13) 0.0240(6) Uani 1 1 d . . H13 H 0.5602 0.3340 0.6402 0.029 Uiso 1 1 calc R U C14 C 0.7686(3) 0.4177(3) 0.63697(14) 0.0317(7) Uani 1 1 d . . H14A H 0.8402 0.4479 0.6701 0.038 Uiso 1 1 calc R U H14B H 0.8075 0.3601 0.6040 0.038 Uiso 1 1 calc R U C15 C 0.6531(4) 0.5001(3) 0.61318(16) 0.0329(7) Uani 1 1 d . . H15A H 0.6209 0.4935 0.5655 0.040 Uiso 1 1 calc R U H15B H 0.6535 0.5813 0.6316 0.040 Uiso 1 1 calc R U C16 C 0.2024(3) 0.3341(2) 0.81287(12) 0.0184(6) Uani 1 1 d . . C17 C 0.0551(3) 0.3335(2) 0.79812(13) 0.0207(6) Uani 1 1 d . . H17 H 0.0261 0.3269 0.7521 0.025 Uiso 1 1 calc R U C18 C -0.0518(3) 0.3422(2) 0.84741(13) 0.0225(6) Uani 1 1 d . . H18 H -0.1517 0.3423 0.8355 0.027 Uiso 1 1 calc R U C19 C -0.0088(3) 0.3507(2) 0.91444(13) 0.0210(6) Uani 1 1 d . . C20 C 0.1374(3) 0.3475(2) 0.93143(13) 0.0218(6) Uani 1 1 d . . H20 H 0.1649 0.3518 0.9778 0.026 Uiso 1 1 calc R U C21 C 0.2443(3) 0.3381(2) 0.88219(13) 0.0199(6) Uani 1 1 d . . C22 C 0.4004(3) 0.3360(2) 0.90369(13) 0.0225(6) Uani 1 1 d . . H22A H 0.4435 0.4139 0.8965 0.034 Uiso 1 1 calc R U H22B H 0.4532 0.2774 0.8768 0.034 Uiso 1 1 calc R U H22C H 0.4066 0.3152 0.9518 0.034 Uiso 1 1 calc R U C23 C -0.2528(3) 0.3793(3) 0.95107(15) 0.0283(7) Uani 1 1 d . . H23A H -0.2641 0.4493 0.9224 0.042 Uiso 1 1 calc R U H23B H -0.3097 0.3892 0.9927 0.042 Uiso 1 1 calc R U H23C H -0.2873 0.3097 0.9265 0.042 Uiso 1 1 calc R U N1 N 0.4023(2) 0.44499(17) 0.75651(10) 0.0170(4) Uani 1 1 d . . N2 N 0.1848(2) 0.22074(18) 0.66306(10) 0.0193(5) Uani 1 1 d . . H2 H 0.1873 0.1515 0.6831 0.023 Uiso 1 1 calc R U O1 O 0.6215(2) 0.32993(16) 0.78399(9) 0.0224(4) Uani 1 1 d . . O2 O 0.6424(2) 0.54305(16) 0.76278(10) 0.0257(4) Uani 1 1 d . . O3 O -0.1033(2) 0.36434(18) 0.96804(9) 0.0272(5) Uani 1 1 d . . S1 S 0.57727(7) 0.43160(5) 0.74600(3) 0.01760(16) 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 0.0167(12) 0.0140(11) 0.0210(12) -0.0001(10) -0.0042(11) -0.0011(9) C2 0.0140(13) 0.0171(13) 0.0212(13) -0.0018(10) -0.0001(10) 0.0001(10) C3 0.0162(14) 0.0231(13) 0.0195(12) -0.0011(10) 0.0007(10) 0.0025(11) C4 0.0275(16) 0.0237(15) 0.0253(13) -0.0041(11) -0.0015(11) 0.0014(12) C5 0.0233(15) 0.0389(17) 0.0221(13) -0.0101(12) -0.0042(11) 0.0034(12) C6 0.0246(16) 0.0421(17) 0.0220(13) 0.0034(12) -0.0038(12) 0.0076(13) C7 0.0234(15) 0.0281(15) 0.0227(12) 0.0051(11) 0.0006(11) 0.0033(12) C8 0.0145(13) 0.0236(14) 0.0205(12) 0.0009(10) 0.0032(10) 0.0018(11) C9 0.0138(13) 0.0211(13) 0.0218(12) 0.0011(11) 0.0016(10) 0.0011(10) C10 0.0224(15) 0.0189(13) 0.0306(14) 0.0045(11) -0.0049(12) -0.0009(11) C11 0.0182(13) 0.0136(12) 0.0310(13) 0.0021(10) -0.0016(10) 0.0005(10) C12 0.0254(15) 0.0192(13) 0.0398(15) -0.0008(11) 0.0046(13) 0.0029(11) C13 0.0243(15) 0.0247(14) 0.0230(13) -0.0014(11) 0.0006(11) 0.0013(11) C14 0.0256(16) 0.0408(18) 0.0286(14) 0.0031(13) 0.0068(12) 0.0037(14) C15 0.0330(18) 0.0374(17) 0.0284(14) 0.0074(13) 0.0047(13) -0.0021(14) C16 0.0190(14) 0.0148(13) 0.0213(12) 0.0011(10) -0.0021(11) -0.0007(10) C17 0.0213(14) 0.0214(13) 0.0193(12) 0.0010(10) -0.0030(11) -0.0027(11) C18 0.0174(14) 0.0213(13) 0.0287(13) 0.0011(11) -0.0007(11) -0.0012(11) C19 0.0216(15) 0.0179(12) 0.0234(13) 0.0002(11) 0.0041(11) -0.0017(11) C20 0.0253(15) 0.0213(13) 0.0187(12) -0.0006(10) -0.0037(11) -0.0012(12) C21 0.0211(14) 0.0168(13) 0.0219(13) -0.0003(10) -0.0027(11) -0.0002(10) C22 0.0197(15) 0.0273(14) 0.0205(12) -0.0005(10) -0.0014(10) 0.0001(11) C23 0.0185(15) 0.0377(17) 0.0288(14) -0.0014(12) 0.0030(11) -0.0003(12) N1 0.0148(11) 0.0144(10) 0.0219(10) 0.0000(9) -0.0023(9) -0.0011(8) N2 0.0230(12) 0.0146(11) 0.0202(10) 0.0004(8) -0.0042(9) -0.0003(9) O1 0.0182(10) 0.0231(10) 0.0258(9) 0.0010(8) -0.0039(8) 0.0022(8) O2 0.0183(10) 0.0230(9) 0.0358(11) -0.0061(8) -0.0036(8) -0.0017(8) O3 0.0213(11) 0.0374(11) 0.0230(9) 0.0004(8) 0.0015(8) 0.0016(9) S1 0.0149(3) 0.0174(3) 0.0206(3) -0.0017(3) -0.0011(3) -0.0003(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 C2 C1 N1 107.3(2) C2 C1 C16 112.5(2) N1 C1 C16 111.1(2) C2 C1 H1 108.6 N1 C1 H1 108.6 C16 C1 H1 108.6 C9 C2 N2 110.4(2) C9 C2 C1 125.7(2) N2 C2 C1 123.6(2) N2 C3 C4 130.1(2) N2 C3 C8 107.8(2) C4 C3 C8 122.1(2) C5 C4 C3 117.5(3) C5 C4 H4 121.3 C3 C4 H4 121.3 C4 C5 C6 121.4(3) C4 C5 H5 119.3 C6 C5 H5 119.3 C7 C6 C5 120.9(3) C7 C6 H6 119.6 C5 C6 H6 119.6 C6 C7 C8 119.0(3) C6 C7 H7 120.5 C8 C7 H7 120.5 C7 C8 C3 119.2(3) C7 C8 C9 133.9(3) C3 C8 C9 106.9(2) C2 C9 C8 106.5(2) C2 C9 C10 123.5(2) C8 C9 C10 129.9(2) C9 C10 C11 111.7(2) C9 C10 H10A 109.3 C11 C10 H10A 109.3 C9 C10 H10B 109.3 C11 C10 H10B 109.3 H10A C10 H10B 107.9 N1 C11 C12 110.9(2) N1 C11 C10 112.4(2) C12 C11 C10 112.4(2) N1 C11 H11 106.9 C12 C11 H11 106.9 C10 C11 H11 106.9 C11 C12 H12A 109.5 C11 C12 H12B 109.5 H12A C12 H12B 109.5 C11 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 C15 C13 C14 59.49(19) C15 C13 S1 120.1(2) C14 C13 S1 117.3(2) C15 C13 H13 116.0 C14 C13 H13 116.0 S1 C13 H13 116.0 C15 C14 C13 60.07(19) C15 C14 H14A 117.8 C13 C14 H14A 117.8 C15 C14 H14B 117.8 C13 C14 H14B 117.8 H14A C14 H14B 114.9 C14 C15 C13 60.44(19) C14 C15 H15A 117.7 C13 C15 H15A 117.7 C14 C15 H15B 117.7 C13 C15 H15B 117.7 H15A C15 H15B 114.8 C17 C16 C21 117.9(2) C17 C16 C1 120.5(2) C21 C16 C1 121.6(2) C18 C17 C16 123.2(2) C18 C17 H17 118.4 C16 C17 H17 118.4 C19 C18 C17 118.1(3) C19 C18 H18 120.9 C17 C18 H18 120.9 O3 C19 C18 124.1(2) O3 C19 C20 115.5(2) C18 C19 C20 120.4(2) C21 C20 C19 121.5(2) C21 C20 H20 119.3 C19 C20 H20 119.3 C20 C21 C16 118.9(2) C20 C21 C22 119.0(2) C16 C21 C22 122.1(2) C21 C22 H22A 109.5 C21 C22 H22B 109.5 H22A C22 H22B 109.5 C21 C22 H22C 109.5 H22A C22 H22C 109.5 H22B C22 H22C 109.5 O3 C23 H23A 109.5 O3 C23 H23B 109.5 H23A C23 H23B 109.5 O3 C23 H23C 109.5 H23A C23 H23C 109.5 H23B C23 H23C 109.5 C1 N1 C11 117.32(19) C1 N1 S1 117.04(15) C11 N1 S1 117.07(16) C3 N2 C2 108.4(2) C3 N2 H2 125.8 C2 N2 H2 125.8 C19 O3 C23 116.3(2) O1 S1 O2 117.94(11) O1 S1 N1 106.79(11) O2 S1 N1 107.51(11) O1 S1 C13 106.88(12) O2 S1 C13 108.08(13) N1 S1 C13 109.46(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.495(3) C1 N1 1.499(3) C1 C16 1.522(4) C1 H1 1.0000 C2 C9 1.359(4) C2 N2 1.384(3) C3 N2 1.378(3) C3 C4 1.391(4) C3 C8 1.411(4) C4 C5 1.389(4) C4 H4 0.9500 C5 C6 1.394(4) C5 H5 0.9500 C6 C7 1.389(4) C6 H6 0.9500 C7 C8 1.397(4) C7 H7 0.9500 C8 C9 1.442(4) C9 C10 1.501(4) C10 C11 1.543(4) C10 H10A 0.9900 C10 H10B 0.9900 C11 N1 1.503(3) C11 C12 1.523(4) C11 H11 1.0000 C12 H12A 0.9800 C12 H12B 0.9800 C12 H12C 0.9800 C13 C15 1.501(4) C13 C14 1.507(4) C13 S1 1.751(3) C13 H13 1.0000 C14 C15 1.492(4) C14 H14A 0.9900 C14 H14B 0.9900 C15 H15A 0.9900 C15 H15B 0.9900 C16 C17 1.388(4) C16 C21 1.421(4) C17 C18 1.388(4) C17 H17 0.9500 C18 C19 1.384(4) C18 H18 0.9500 C19 O3 1.378(3) C19 C20 1.389(4) C20 C21 1.388(4) C20 H20 0.9500 C21 C22 1.500(4) C22 H22A 0.9800 C22 H22B 0.9800 C22 H22C 0.9800 C23 O3 1.428(3) C23 H23A 0.9800 C23 H23B 0.9800 C23 H23C 0.9800 N1 S1 1.633(2) N2 H2 0.8800 O1 S1 1.4349(19) O2 S1 1.4384(18)