#------------------------------------------------------------------------------ #$Date: 2016-03-18 09:58:37 +0200 (Fri, 18 Mar 2016) $ #$Revision: 178327 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/46/7224639.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_7224639 loop_ _publ_author_name 'Baig, Noorullah' 'Madduluri, Vimal Kumar' 'Sah, Ajay K.' _publ_section_title ; Selective oxidation of organic sulfides to sulfoxides using sugar derived cis-dioxo molybdenum(vi) complexes: kinetic and mechanistic studies ; _journal_issue 33 _journal_name_full 'RSC Adv.' _journal_page_first 28015 _journal_paper_doi 10.1039/C6RA01087C _journal_volume 6 _journal_year 2016 _chemical_formula_moiety 'C23 H17 N O S' _chemical_formula_sum 'C23 H17 N O S' _chemical_formula_weight 355.43 _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 _audit_creation_date 2015-11-30 _audit_creation_method ; Olex2 1.2 (compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103) ; _audit_update_record ; 2016-01-04 deposited with the CCDC. 2016-03-03 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.132(2) _cell_length_b 14.536(5) _cell_length_c 19.327(7) _cell_measurement_reflns_used 3219 _cell_measurement_temperature 100 _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 3.5 _cell_volume 1722.7(10) _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011) ; _computing_data_collection ; CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 100 _diffrn_detector CCD _diffrn_detector_area_resol_mean 13.6612 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_details ; scan: Number of images: 533 Slice: -69.0000 - 90.9000 Image width: 0.3000 Exp time: 20.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.8600 2theta: 29.8900 scan: Number of images: 334 Slice: 4.0000 - 104.2000 Image width: 0.3000 Exp time: 20.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 180.0000 XTD: 49.8600 2theta: 29.8900 scan: Number of images: 334 Slice: 4.0000 - 104.2000 Image width: 0.3000 Exp time: 20.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 90.0000 XTD: 49.8600 2theta: 29.8900 ; _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support Fiber _diffrn_orient_matrix_type d*Trek _diffrn_orient_matrix_UB_11 -0.158229 _diffrn_orient_matrix_UB_12 -0.035656 _diffrn_orient_matrix_UB_13 0.017044 _diffrn_orient_matrix_UB_21 -0.014484 _diffrn_orient_matrix_UB_22 0.037634 _diffrn_orient_matrix_UB_23 -0.055737 _diffrn_orient_matrix_UB_31 0.006207 _diffrn_orient_matrix_UB_32 -0.041809 _diffrn_orient_matrix_UB_33 -0.029843 _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.1318 _diffrn_reflns_av_unetI/netI 0.1430 _diffrn_reflns_laue_measured_fraction_full 0.996 _diffrn_reflns_laue_measured_fraction_max 0.989 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 11726 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.989 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.542 _diffrn_reflns_theta_min 3.459 _diffrn_source 'Sealed Tube' _diffrn_source_current 12.0 _diffrn_source_power 0.6 _diffrn_source_voltage 50.0 _exptl_absorpt_coefficient_mu 0.200 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.683 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Blessings, 1995' _exptl_crystal_colour 'clear light yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.371 _exptl_crystal_description needle _exptl_crystal_F_000 744 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.922 _refine_diff_density_min -0.496 _refine_diff_density_rms 0.095 _refine_ls_abs_structure_details ; Flack x determined using 567 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.08(17) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 236 _refine_ls_number_reflns 3922 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.018 _refine_ls_R_factor_all 0.1416 _refine_ls_R_factor_gt 0.0910 _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^)+(0.1367P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2135 _refine_ls_wR_factor_ref 0.2693 _reflns_Friedel_coverage 0.730 _reflns_friedel_fraction_full 0.998 _reflns_friedel_fraction_max 0.989 _reflns_number_gt 2163 _reflns_number_total 3922 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL mk17s_100k_a.res in P2(1)2(1)2(1) REM Old TITL MK17S_100K in P212121 #19 REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.158, Rweak 0.035, Alpha 0.001, Orientation as input REM Flack x = 0.063 ( 0.174 ) from Parsons' quotients REM Formula found by SHELXT: C23 N O S CELL 0.71075 6.1316 14.5361 19.3271 90 90 90 ZERR 4 0.0021 0.0053 0.0072 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N O S UNIT 92 68 4 4 4 L.S. 8 PLAN 20 TEMP -173.15 BOND $H LIST 6 fmap 2 MORE -1 CONF ACTA REM REM REM WGHT 0.136700 FVAR 0.81723 S1 5 0.112303 0.806925 0.650690 11.00000 0.04455 0.03211 = 0.04309 0.00608 -0.00722 -0.00871 O1 4 0.503562 0.872207 0.770312 11.00000 0.04118 0.02951 = 0.04754 0.00545 -0.00562 -0.00439 AFIX 147 H1 2 0.398440 0.836896 0.761862 11.00000 -1.50000 AFIX 0 N1 3 0.282735 0.723831 0.771852 11.00000 0.02765 0.02317 = 0.04878 -0.00304 -0.00389 -0.00490 C10 1 0.751322 0.704936 0.890432 11.00000 0.02713 0.02474 = 0.03375 -0.00453 0.00442 0.00051 C19 1 -0.017743 0.835965 0.519039 11.00000 0.03542 0.03237 = 0.04094 -0.00160 0.00064 -0.00189 AFIX 43 H19 2 0.118433 0.809679 0.506438 11.00000 -1.20000 AFIX 0 C12 1 0.102591 0.673622 0.746606 11.00000 0.03033 0.02005 = 0.03458 -0.00558 0.00443 -0.00316 C3 1 0.640811 0.831137 0.815892 11.00000 0.03441 0.02321 = 0.03585 0.00350 -0.00136 0.00556 C11 1 0.944291 0.753479 0.906319 11.00000 0.03145 0.03446 = 0.02910 -0.00688 -0.00539 0.00367 C14 1 -0.186922 0.661338 0.661138 11.00000 0.03561 0.02747 = 0.04493 0.00285 -0.00452 0.00246 AFIX 43 H14 2 -0.257500 0.684140 0.620881 11.00000 -1.20000 AFIX 0 C16 1 -0.158849 0.548437 0.750993 11.00000 0.03325 0.02345 = 0.04681 -0.00116 -0.00316 0.00365 AFIX 43 H16 2 -0.211204 0.493896 0.772381 11.00000 -1.20000 AFIX 0 C2 1 0.598841 0.743296 0.840635 11.00000 0.03498 0.02447 = 0.02825 -0.00362 0.00530 -0.00234 C17 1 0.023148 0.592556 0.777515 11.00000 0.03488 0.02359 = 0.02820 0.00604 0.00409 0.00155 AFIX 43 H17 2 0.095004 0.567891 0.816914 11.00000 -1.20000 AFIX 0 C13 1 -0.005699 0.706524 0.687234 11.00000 0.03288 0.02570 = 0.03981 0.00202 0.00335 -0.00186 C1 1 0.418188 0.689933 0.815258 11.00000 0.03302 0.02449 = 0.02732 -0.00179 0.00263 0.00656 AFIX 43 H1A 2 0.399170 0.628536 0.830986 11.00000 -1.20000 AFIX 0 C20 1 -0.159832 0.870645 0.467994 11.00000 0.04107 0.02890 = 0.03706 0.00208 0.00121 -0.00387 AFIX 43 H20 2 -0.116413 0.871365 0.420813 11.00000 -1.20000 AFIX 0 C23 1 -0.283655 0.874911 0.604978 11.00000 0.03514 0.02783 = 0.05317 0.00133 0.00196 -0.00453 AFIX 43 H23 2 -0.326611 0.876764 0.652185 11.00000 -1.20000 AFIX 0 C6 1 1.102517 0.713063 0.950920 11.00000 0.02794 0.03581 = 0.03096 0.00081 0.00411 -0.00424 AFIX 43 H6 2 1.235115 0.744747 0.959784 11.00000 -1.20000 AFIX 0 C5 1 0.979688 0.842071 0.877240 11.00000 0.03896 0.02306 = 0.03957 -0.00082 -0.00324 -0.00445 AFIX 43 H5 2 1.109555 0.874718 0.887996 11.00000 -1.20000 AFIX 0 C22 1 -0.424270 0.906027 0.554784 11.00000 0.04729 0.02660 = 0.04632 -0.00374 0.01001 0.00468 AFIX 43 H22 2 -0.563544 0.929052 0.567585 11.00000 -1.20000 AFIX 0 C7 1 1.067091 0.630594 0.980740 11.00000 0.03604 0.02610 = 0.04131 -0.00043 -0.00634 0.00817 AFIX 43 H7 2 1.174413 0.604226 1.010125 11.00000 -1.20000 AFIX 0 C15 1 -0.265093 0.583535 0.693316 11.00000 0.03295 0.03157 = 0.03976 -0.00390 -0.00197 0.00072 AFIX 43 H15 2 -0.391889 0.553831 0.676030 11.00000 -1.20000 AFIX 0 C18 1 -0.079316 0.840768 0.587418 11.00000 0.03793 0.02119 = 0.04333 0.00206 -0.00414 -0.00880 C4 1 0.831363 0.880269 0.834633 11.00000 0.04659 0.02132 = 0.04265 0.00535 -0.00176 -0.00487 AFIX 43 H4 2 0.854658 0.940502 0.817048 11.00000 -1.20000 AFIX 0 C21 1 -0.365874 0.904123 0.487235 11.00000 0.04233 0.02512 = 0.05392 0.01369 -0.00724 0.00077 AFIX 43 H21 2 -0.464359 0.925450 0.452847 11.00000 -1.20000 AFIX 0 C8 1 0.865440 0.582636 0.967792 11.00000 0.04059 0.02623 = 0.03951 0.00342 0.00094 0.00351 AFIX 43 H8 2 0.837146 0.525361 0.989698 11.00000 -1.20000 AFIX 0 C9 1 0.714735 0.620192 0.923667 11.00000 0.04527 0.02355 = 0.04429 -0.00814 -0.00480 -0.00053 AFIX 43 H9 2 0.582228 0.588198 0.915312 11.00000 -1.20000 AFIX 0 HKLF 4 REM mk17s_100k_a.res in P2(1)2(1)2(1) REM R1 = 0.0910 for 2163 Fo > 4sig(Fo) and 0.1416 for all 3922 data REM 236 parameters refined using 0 restraints END WGHT 0.1366 0.0000 REM Highest difference peak 0.922, deepest hole -0.496, 1-sigma level 0.095 Q1 1 1.2386 0.7405 0.9056 11.00000 0.05 0.36 Q2 1 -0.3246 0.8062 0.6516 11.00000 0.05 0.35 Q3 1 0.9839 0.7456 0.9165 11.00000 0.05 0.34 Q4 1 -0.1667 0.9608 0.6582 11.00000 0.05 0.33 Q5 1 0.3378 0.6147 0.9185 11.00000 0.05 0.32 Q6 1 0.0088 0.8135 0.7264 11.00000 0.05 0.31 Q7 1 -0.0019 0.8877 0.3766 11.00000 0.05 0.31 Q8 1 -0.3737 0.4179 0.8310 11.00000 0.05 0.31 Q9 1 -0.1916 0.4992 0.8450 11.00000 0.05 0.30 Q10 1 0.1208 0.5928 0.6467 11.00000 0.05 0.30 Q11 1 0.0188 0.8368 0.4243 11.00000 0.05 0.30 Q12 1 0.7200 0.9450 0.9046 11.00000 0.05 0.29 Q13 1 -0.5771 1.0154 0.4322 11.00000 0.05 0.29 Q14 1 -0.2235 0.8025 0.5928 11.00000 0.05 0.28 Q15 1 -0.0134 0.8204 0.5928 11.00000 0.05 0.28 Q16 1 0.4232 0.7059 0.7060 11.00000 0.05 0.28 Q17 1 1.2838 0.8250 1.0071 11.00000 0.05 0.27 Q18 1 -0.1434 0.8187 0.3466 11.00000 0.05 0.27 Q19 1 -0.6874 0.9365 0.5577 11.00000 0.05 0.27 Q20 1 1.1205 0.5797 1.0486 11.00000 0.05 0.26 REM The information below was added by Olex2. REM REM R1 = 0.0910 for 2163 Fo > 4sig(Fo) and 0.1416 for all 11776 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.92, deepest hole -0.50 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.1416 REM R1_gt = 0.0910 REM wR_ref = 0.2693 REM GOOF = 1.018 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 11776 REM Reflections_gt = 2163 REM Parameters = n/a REM Hole = -0.50 REM Peak = 0.92 REM Flack = 0.08(17) ; _cod_data_source_file c6ra01087c2.cif _cod_data_source_block AKSsulfide_100k _cod_original_cell_volume 1722.6(11) _cod_database_code 7224639 _shelxl_version_number 2014/6 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All O(H) groups 2.a Aromatic/amide H refined with riding coordinates: C19(H19), C14(H14), C16(H16), C17(H17), C1(H1A), C20(H20), C23(H23), C6(H6), C5(H5), C22(H22), C7(H7), C15(H15), C4(H4), C21(H21), C8(H8), C9(H9) 2.b Idealised tetrahedral OH refined as rotating group: O1(H1) ; _olex2_submission_special_instructions 'No special instructions were received' 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 S1 S 0.1123(4) 0.80693(14) 0.65069(11) 0.0399(6) Uani 1 1 d . O1 O 0.5036(11) 0.8722(4) 0.7703(3) 0.0394(14) Uani 1 1 d . H1 H 0.3984 0.8369 0.7619 0.059 Uiso 1 1 calc GR N1 N 0.2827(11) 0.7238(4) 0.7719(4) 0.0332(16) Uani 1 1 d . C10 C 0.7513(13) 0.7049(5) 0.8904(4) 0.0285(16) Uani 1 1 d . C19 C -0.0177(15) 0.8360(6) 0.5190(4) 0.0362(18) Uani 1 1 d . H19 H 0.1184 0.8097 0.5064 0.043 Uiso 1 1 calc R C12 C 0.1026(13) 0.6736(5) 0.7466(4) 0.0283(16) Uani 1 1 d . C3 C 0.6408(13) 0.8311(5) 0.8159(4) 0.0312(17) Uani 1 1 d . C11 C 0.9443(13) 0.7535(6) 0.9063(4) 0.0317(18) Uani 1 1 d . C14 C -0.1869(13) 0.6613(5) 0.6611(4) 0.0360(18) Uani 1 1 d . H14 H -0.2575 0.6841 0.6209 0.043 Uiso 1 1 calc R C16 C -0.1588(14) 0.5484(5) 0.7510(4) 0.0345(19) Uani 1 1 d . H16 H -0.2112 0.4939 0.7724 0.041 Uiso 1 1 calc R C2 C 0.5988(13) 0.7433(5) 0.8406(4) 0.0292(16) Uani 1 1 d . C17 C 0.0231(13) 0.5926(5) 0.7775(4) 0.0289(17) Uani 1 1 d . H17 H 0.0950 0.5679 0.8169 0.035 Uiso 1 1 calc R C13 C -0.0057(14) 0.7065(5) 0.6872(4) 0.0328(17) Uani 1 1 d . C1 C 0.4182(12) 0.6899(5) 0.8153(4) 0.0283(16) Uani 1 1 d . H1A H 0.3992 0.6285 0.8310 0.034 Uiso 1 1 calc R C20 C -0.1598(15) 0.8706(5) 0.4680(4) 0.036(2) Uani 1 1 d . H20 H -0.1164 0.8714 0.4208 0.043 Uiso 1 1 calc R C23 C -0.2837(14) 0.8749(5) 0.6050(5) 0.039(2) Uani 1 1 d . H23 H -0.3266 0.8768 0.6522 0.046 Uiso 1 1 calc R C6 C 1.1025(14) 0.7131(5) 0.9509(4) 0.0316(17) Uani 1 1 d . H6 H 1.2351 0.7447 0.9598 0.038 Uiso 1 1 calc R C5 C 0.9797(15) 0.8421(5) 0.8772(4) 0.0339(18) Uani 1 1 d . H5 H 1.1096 0.8747 0.8880 0.041 Uiso 1 1 calc R C22 C -0.4243(16) 0.9060(5) 0.5548(4) 0.040(2) Uani 1 1 d . H22 H -0.5635 0.9291 0.5676 0.048 Uiso 1 1 calc R C7 C 1.0671(13) 0.6306(5) 0.9807(4) 0.0345(19) Uani 1 1 d . H7 H 1.1744 0.6042 1.0101 0.041 Uiso 1 1 calc R C15 C -0.2651(14) 0.5835(5) 0.6933(4) 0.0348(18) Uani 1 1 d . H15 H -0.3919 0.5538 0.6760 0.042 Uiso 1 1 calc R C18 C -0.0793(14) 0.8408(5) 0.5874(4) 0.0342(19) Uani 1 1 d . C4 C 0.8314(14) 0.8803(5) 0.8346(4) 0.037(2) Uani 1 1 d . H4 H 0.8547 0.9405 0.8170 0.044 Uiso 1 1 calc R C21 C -0.3659(16) 0.9041(5) 0.4872(5) 0.040(2) Uani 1 1 d . H21 H -0.4644 0.9254 0.4528 0.049 Uiso 1 1 calc R C8 C 0.8654(15) 0.5826(5) 0.9678(4) 0.0354(19) Uani 1 1 d . H8 H 0.8371 0.5254 0.9897 0.043 Uiso 1 1 calc R C9 C 0.7147(16) 0.6202(5) 0.9237(4) 0.038(2) Uani 1 1 d . H9 H 0.5822 0.5882 0.9153 0.045 Uiso 1 1 calc R 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 0.0445(13) 0.0321(10) 0.0431(11) 0.0061(9) -0.0072(11) -0.0087(10) O1 0.041(3) 0.030(3) 0.048(3) 0.005(3) -0.006(3) -0.004(3) N1 0.028(4) 0.023(3) 0.049(4) -0.003(3) -0.004(3) -0.005(3) C10 0.027(4) 0.025(3) 0.034(4) -0.005(3) 0.004(3) 0.001(3) C19 0.035(4) 0.032(4) 0.041(4) -0.002(4) 0.001(4) -0.002(4) C12 0.030(4) 0.020(3) 0.035(4) -0.006(3) 0.004(4) -0.003(3) C3 0.034(4) 0.023(3) 0.036(4) 0.004(3) -0.001(4) 0.006(3) C11 0.031(5) 0.034(4) 0.029(4) -0.007(3) -0.005(3) 0.004(4) C14 0.036(4) 0.027(3) 0.045(4) 0.003(4) -0.005(4) 0.002(4) C16 0.033(5) 0.023(4) 0.047(4) -0.001(3) -0.003(4) 0.004(4) C2 0.035(4) 0.024(3) 0.028(3) -0.004(3) 0.005(4) -0.002(3) C17 0.035(4) 0.024(3) 0.028(3) 0.006(3) 0.004(4) 0.002(4) C13 0.033(4) 0.026(4) 0.040(4) 0.002(3) 0.003(4) -0.002(4) C1 0.033(4) 0.024(3) 0.027(3) -0.002(3) 0.003(3) 0.007(4) C20 0.041(5) 0.029(4) 0.037(4) 0.002(3) 0.001(4) -0.004(4) C23 0.035(5) 0.028(4) 0.053(5) 0.001(4) 0.002(4) -0.005(4) C6 0.028(4) 0.036(4) 0.031(4) 0.001(3) 0.004(4) -0.004(4) C5 0.039(5) 0.023(3) 0.040(4) -0.001(3) -0.003(4) -0.004(4) C22 0.047(6) 0.027(4) 0.046(5) -0.004(4) 0.010(5) 0.005(4) C7 0.036(5) 0.026(4) 0.041(4) 0.000(3) -0.006(4) 0.008(4) C15 0.033(4) 0.032(4) 0.040(4) -0.004(3) -0.002(4) 0.001(4) C18 0.038(5) 0.021(3) 0.043(4) 0.002(3) -0.004(4) -0.009(4) C4 0.047(5) 0.021(3) 0.043(4) 0.005(3) -0.002(4) -0.005(4) C21 0.042(5) 0.025(4) 0.054(5) 0.014(4) -0.007(5) 0.001(4) C8 0.041(5) 0.026(4) 0.040(4) 0.003(3) 0.001(4) 0.004(4) C9 0.045(5) 0.024(4) 0.044(4) -0.008(3) -0.005(4) -0.001(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 C18 S1 C13 103.5(4) C3 O1 H1 109.5 C1 N1 C12 122.4(6) C11 C10 C2 119.4(7) C9 C10 C11 118.2(8) C9 C10 C2 122.4(7) C20 C19 H19 120.5 C18 C19 H19 120.5 C18 C19 C20 119.0(8) C17 C12 N1 123.8(7) C17 C12 C13 117.8(7) C13 C12 N1 118.3(7) O1 C3 C2 120.9(7) O1 C3 C4 117.1(6) C2 C3 C4 121.9(7) C10 C11 C6 119.8(7) C10 C11 C5 119.7(7) C5 C11 C6 120.6(8) C13 C14 H14 119.9 C15 C14 H14 119.9 C15 C14 C13 120.3(8) C17 C16 H16 119.8 C17 C16 C15 120.3(7) C15 C16 H16 119.8 C3 C2 C10 117.5(7) C3 C2 C1 121.4(7) C1 C2 C10 121.0(6) C12 C17 H17 119.7 C16 C17 C12 120.6(7) C16 C17 H17 119.7 C12 C13 S1 114.3(6) C14 C13 S1 124.9(6) C14 C13 C12 120.9(7) N1 C1 C2 121.1(7) N1 C1 H1A 119.5 C2 C1 H1A 119.5 C19 C20 H20 120.2 C21 C20 C19 119.7(8) C21 C20 H20 120.2 C22 C23 H23 119.6 C22 C23 C18 120.7(9) C18 C23 H23 119.6 C11 C6 H6 119.5 C7 C6 C11 121.1(8) C7 C6 H6 119.5 C11 C5 H5 119.6 C4 C5 C11 120.8(8) C4 C5 H5 119.6 C23 C22 H22 119.7 C21 C22 C23 120.5(9) C21 C22 H22 119.7 C6 C7 H7 120.2 C6 C7 C8 119.6(8) C8 C7 H7 120.2 C14 C15 C16 120.1(8) C14 C15 H15 120.0 C16 C15 H15 120.0 C19 C18 S1 117.9(7) C19 C18 C23 120.0(8) C23 C18 S1 122.0(7) C3 C4 H4 119.8 C5 C4 C3 120.4(7) C5 C4 H4 119.8 C20 C21 H21 120.0 C22 C21 C20 120.0(8) C22 C21 H21 120.0 C7 C8 H8 120.2 C9 C8 C7 119.6(7) C9 C8 H8 120.2 C10 C9 H9 119.2 C8 C9 C10 121.7(8) C8 C9 H9 119.2 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C13 1.775(8) S1 C18 1.766(8) O1 H1 0.8400 O1 C3 1.357(9) N1 C12 1.411(9) N1 C1 1.279(10) C10 C11 1.411(11) C10 C2 1.453(11) C10 C9 1.407(11) C19 H19 0.9500 C19 C20 1.409(12) C19 C18 1.376(11) C12 C17 1.408(10) C12 C13 1.409(11) C3 C2 1.388(10) C3 C4 1.416(12) C11 C6 1.425(11) C11 C5 1.422(11) C14 H14 0.9500 C14 C13 1.386(12) C14 C15 1.377(12) C16 H16 0.9500 C16 C17 1.385(11) C16 C15 1.388(11) C2 C1 1.438(11) C17 H17 0.9500 C1 H1A 0.9500 C20 H20 0.9500 C20 C21 1.404(13) C23 H23 0.9500 C23 C22 1.374(12) C23 C18 1.390(12) C6 H6 0.9500 C6 C7 1.348(11) C5 H5 0.9500 C5 C4 1.347(11) C22 H22 0.9500 C22 C21 1.354(12) C7 H7 0.9500 C7 C8 1.441(12) C15 H15 0.9500 C4 H4 0.9500 C21 H21 0.9500 C8 H8 0.9500 C8 C9 1.371(12) C9 H9 0.9500 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 O1 C3 C2 C10 -178.7(7) O1 C3 C2 C1 4.6(11) O1 C3 C4 C5 -177.1(7) N1 C12 C17 C16 178.0(7) N1 C12 C13 S1 2.3(9) N1 C12 C13 C14 -178.4(7) C10 C11 C6 C7 -2.9(11) C10 C11 C5 C4 -0.1(11) C10 C2 C1 N1 179.4(7) C19 C20 C21 C22 2.3(12) C12 N1 C1 C2 -179.3(6) C3 C2 C1 N1 -4.1(11) C11 C10 C2 C3 -6.2(10) C11 C10 C2 C1 170.4(7) C11 C10 C9 C8 -3.2(11) C11 C6 C7 C8 -0.4(11) C11 C5 C4 C3 -2.5(12) C2 C10 C11 C6 -175.1(6) C2 C10 C11 C5 4.4(10) C2 C10 C9 C8 176.5(7) C2 C3 C4 C5 0.5(12) C17 C12 C13 S1 -178.1(6) C17 C12 C13 C14 1.2(11) C17 C16 C15 C14 1.5(12) C13 S1 C18 C19 -113.5(7) C13 S1 C18 C23 69.1(7) C13 C12 C17 C16 -1.6(11) C13 C14 C15 C16 -1.8(12) C1 N1 C12 C17 15.9(11) C1 N1 C12 C13 -164.5(7) C20 C19 C18 S1 -174.1(6) C20 C19 C18 C23 3.4(12) C23 C22 C21 C20 -0.3(13) C6 C11 C5 C4 179.5(7) C6 C7 C8 C9 1.9(12) C5 C11 C6 C7 177.6(8) C22 C23 C18 S1 175.9(6) C22 C23 C18 C19 -1.4(12) C7 C8 C9 C10 -0.1(12) C15 C14 C13 S1 179.7(6) C15 C14 C13 C12 0.4(12) C15 C16 C17 C12 0.2(11) C18 S1 C13 C12 -171.2(6) C18 S1 C13 C14 9.5(8) C18 C19 C20 C21 -3.8(12) C18 C23 C22 C21 -0.1(12) C4 C3 C2 C10 3.8(11) C4 C3 C2 C1 -172.8(7) C9 C10 C11 C6 4.6(10) C9 C10 C11 C5 -175.8(7) C9 C10 C2 C3 174.1(7) C9 C10 C2 C1 -9.3(11)