#------------------------------------------------------------------------------ #$Date: 2021-07-06 06:56:22 +0300 (Tue, 06 Jul 2021) $ #$Revision: 267271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158158.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_7158158 loop_ _publ_author_name 'Vroemans, Robby' 'Ribone, Sergio' 'Thomas, Joice' 'Van Meervelt, Luc' 'Ollevier, Thierry' 'Dehaen, Wim' _publ_section_title ; Synthesis of homochiral sulfanyl- and sulfoxide-substituted naphthyltriazoles and study of the conformational stability ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D1OB00784J _journal_year 2021 _chemical_formula_moiety 'C26 H21 N3 O2 S' _chemical_formula_sum 'C26 H21 N3 O2 S' _chemical_formula_weight 439.52 _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' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary iterative _audit_creation_date 2016-02-26 _audit_creation_method ; Olex2 1.2 (compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155) ; _audit_update_record ; 2021-04-09 deposited with the CCDC. 2021-07-05 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.84610(10) _cell_length_b 15.7021(3) _cell_length_c 21.1251(4) _cell_measurement_reflns_used 5702 _cell_measurement_temperature 100.03(10) _cell_measurement_theta_max 28.5660 _cell_measurement_theta_min 3.1210 _cell_volume 2270.91(7) _computing_cell_refinement 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _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 ; Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012) ; _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.03(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 15.9631 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -20.00 25.00 1.00 22.50 -- -17.00 -99.00-120.00 45 2 \w -2.00 88.00 1.00 22.50 -- 19.03 57.00 150.00 90 3 \w -2.00 88.00 1.00 22.50 -- 19.03 57.00 60.00 90 4 \w -93.00 -68.00 1.00 22.50 -- -17.00-178.00-150.00 25 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Single source at offset, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0067055000 _diffrn_orient_matrix_UB_12 -0.0424223000 _diffrn_orient_matrix_UB_13 0.0288672000 _diffrn_orient_matrix_UB_21 -0.0326734000 _diffrn_orient_matrix_UB_22 -0.0069873000 _diffrn_orient_matrix_UB_23 0.0184262000 _diffrn_orient_matrix_UB_31 -0.0041342000 _diffrn_orient_matrix_UB_32 -0.0137989000 _diffrn_orient_matrix_UB_33 -0.0977181000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0351 _diffrn_reflns_av_unetI/netI 0.0438 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 11256 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.214 _diffrn_reflns_theta_max 26.340 _diffrn_reflns_theta_min 2.592 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.170 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.81871 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.286 _exptl_crystal_description block _exptl_crystal_F_000 920 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.207 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.042 _refine_ls_abs_structure_details ; Flack x determined using 1671 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.00(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 290 _refine_ls_number_reflns 4637 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.054 _refine_ls_R_factor_all 0.0419 _refine_ls_R_factor_gt 0.0371 _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^)+(0.0336P)^2^+0.5517P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0831 _refine_ls_wR_factor_ref 0.0865 _reflns_Friedel_coverage 0.743 _reflns_Friedel_fraction_full 0.999 _reflns_Friedel_fraction_max 0.999 _reflns_number_gt 4267 _reflns_number_total 4637 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; wdh1062.res created by SHELXL-2014/7 TITL wdh1062 P 21 21 21 R = 0.04 New: P212121 CELL 0.71 6.8461 15.7021 21.1251 90 90 90 ZERR 4 0.0001 0.0003 0.0004 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,-Z SYMM -X,0.5+Y,0.5-Z SFAC C H N O S UNIT 104 84 12 8 4 L.S. 5 PLAN 5 TEMP -178 BOND $H CONF HTAB fmap 2 acta MORE -1 SHEL 999 0.8 OMIT 0 12 0 OMIT 0 0 8 OMIT 0 5 4 REM REM REM WGHT 0.033600 0.551700 FVAR 4.42624 S16 5 -1.166260 0.923962 0.130674 11.00000 0.02102 0.01681 = 0.01802 0.00091 0.00055 -0.00121 O25 4 -0.669350 0.867820 0.181449 11.00000 0.02508 0.03634 = 0.02707 -0.00954 0.00782 -0.00770 AFIX 3 H25 2 -0.557940 0.888100 0.174299 11.00000 -1.50000 AFIX 0 O32 4 -1.367186 0.957190 0.145428 11.00000 0.02408 0.02424 = 0.02792 0.00099 0.00453 0.00300 N11 3 -1.033144 0.722069 0.225749 11.00000 0.02871 0.01636 = 0.01700 0.00100 -0.00158 -0.00110 N14 3 -1.217472 0.748551 0.145792 11.00000 0.03395 0.01977 = 0.02068 0.00144 -0.00298 -0.00377 N15 3 -1.152152 0.686904 0.181596 11.00000 0.03771 0.01919 = 0.02110 -0.00040 -0.00547 -0.00474 C1 1 -0.909731 0.863925 0.260278 11.00000 0.02091 0.01456 = 0.01697 0.00051 -0.00357 0.00160 C2 1 -0.983815 0.889009 0.320539 11.00000 0.02389 0.01411 = 0.01809 0.00175 -0.00270 0.00369 C3 1 -1.171365 0.863753 0.342126 11.00000 0.02846 0.01708 = 0.02058 0.00028 0.00077 -0.00113 AFIX 43 H3 2 -1.250588 0.828063 0.316447 11.00000 -1.20000 AFIX 0 C4 1 -1.238627 0.890615 0.399820 11.00000 0.03171 0.03034 = 0.02481 0.00261 0.00728 0.00363 AFIX 43 H4 2 -1.364378 0.873161 0.413721 11.00000 -1.20000 AFIX 0 C5 1 -1.125197 0.943438 0.438763 11.00000 0.04391 0.03257 = 0.01978 -0.00580 0.00576 0.00761 AFIX 43 H5 2 -1.173618 0.961447 0.478724 11.00000 -1.20000 AFIX 0 C6 1 -0.944237 0.968820 0.418733 11.00000 0.04189 0.02464 = 0.02175 -0.00717 -0.00603 0.00345 AFIX 43 H6 2 -0.867483 1.004526 0.445176 11.00000 -1.20000 AFIX 0 C7 1 -0.869238 0.942824 0.359276 11.00000 0.02920 0.01822 = 0.02109 -0.00020 -0.00545 0.00431 C8 1 -0.685429 0.970615 0.336310 11.00000 0.02860 0.02441 = 0.02835 -0.00744 -0.00859 -0.00069 AFIX 43 H8 2 -0.607058 1.006393 0.362195 11.00000 -1.20000 AFIX 0 C9 1 -0.618321 0.947487 0.278313 11.00000 0.02168 0.02551 = 0.03202 -0.00167 -0.00027 -0.00327 AFIX 43 H9 2 -0.495283 0.967692 0.263930 11.00000 -1.20000 AFIX 0 C10 1 -0.731216 0.893419 0.239329 11.00000 0.02440 0.02006 = 0.02067 -0.00251 -0.00127 0.00246 C12 1 -1.022873 0.807754 0.218524 11.00000 0.02345 0.01532 = 0.01654 -0.00075 0.00263 -0.00016 C13 1 -1.139556 0.823080 0.166990 11.00000 0.02200 0.01738 = 0.01803 -0.00030 0.00102 -0.00220 C17 1 -1.170583 0.886838 0.050724 11.00000 0.03741 0.01628 = 0.01568 0.00436 0.00034 0.00436 C18 1 -0.995227 0.889717 0.017684 11.00000 0.04827 0.02756 = 0.02672 0.00666 0.01154 0.01068 AFIX 43 H18 2 -0.881563 0.913024 0.036798 11.00000 -1.20000 AFIX 0 C19 1 -0.988443 0.858459 -0.042893 11.00000 0.09018 0.03313 = 0.02579 0.00369 0.01955 0.01976 AFIX 43 H19 2 -0.869255 0.859193 -0.065916 11.00000 -1.20000 AFIX 0 C20 1 -1.154073 0.826232 -0.069987 11.00000 0.13254 0.02325 = 0.01886 0.00293 0.00990 0.02070 AFIX 43 H20 2 -1.147956 0.803689 -0.111672 11.00000 -1.20000 AFIX 0 C21 1 -1.330700 0.825754 -0.037929 11.00000 0.10158 0.02293 = 0.03476 0.00350 -0.03448 0.00014 AFIX 43 H21 2 -1.444830 0.804461 -0.058024 11.00000 -1.20000 AFIX 0 C22 1 -1.340565 0.856801 0.024294 11.00000 0.05169 0.02374 = 0.02463 0.00596 -0.01127 -0.00294 AFIX 43 H22 2 -1.459950 0.857040 0.047216 11.00000 -1.20000 AFIX 0 C23 1 -0.916441 0.669648 0.270102 11.00000 0.03104 0.01861 = 0.02152 0.00251 -0.00318 0.00124 AFIX 13 H23 2 -0.790147 0.700065 0.277485 11.00000 -1.20000 AFIX 0 C24 1 -0.868359 0.584104 0.240010 11.00000 0.05248 0.02166 = 0.02858 0.00465 0.00365 0.01064 AFIX 137 H24A 2 -0.988722 0.551114 0.234599 11.00000 -1.50000 H24B 2 -0.778089 0.552715 0.267431 11.00000 -1.50000 H24C 2 -0.807308 0.593404 0.198623 11.00000 -1.50000 AFIX 0 C26 1 -1.016389 0.660116 0.333652 11.00000 0.03824 0.01657 = 0.02099 0.00340 -0.00159 0.00326 C27 1 -1.201941 0.625033 0.338401 11.00000 0.04142 0.02550 = 0.03461 0.00131 0.00239 -0.00288 AFIX 43 H27 2 -1.269340 0.607506 0.301313 11.00000 -1.20000 AFIX 0 C28 1 -1.289092 0.615549 0.397357 11.00000 0.05971 0.03491 = 0.05043 0.01131 0.02293 -0.00173 AFIX 43 H28 2 -1.415179 0.590681 0.400672 11.00000 -1.20000 AFIX 0 C29 1 -1.191737 0.642453 0.451448 11.00000 0.08860 0.04701 = 0.02863 0.01121 0.01866 0.00447 AFIX 43 H29 2 -1.252763 0.637486 0.491667 11.00000 -1.20000 AFIX 0 C30 1 -1.006604 0.676358 0.446799 11.00000 0.08117 0.04608 = 0.02473 0.00549 -0.01054 0.00738 AFIX 43 H30 2 -0.938643 0.693476 0.483885 11.00000 -1.20000 AFIX 0 C31 1 -0.920111 0.685398 0.388158 11.00000 0.05089 0.03052 = 0.02681 0.00397 -0.00854 0.00325 AFIX 43 H31 2 -0.792936 0.709263 0.385153 11.00000 -1.20000 AFIX 0 HKLF 4 1 0 0 -1 0 1 0 1 0 0 REM wdh1062 P 21 21 21 R = 0.04 New: P212121 REM R1 = 0.0371 for 4267 Fo > 4sig(Fo) and 0.0419 for all 4637 data REM 290 parameters refined using 0 restraints END WGHT 0.0336 0.5497 REM Instructions for potential hydrogen bonds EQIV $1 x+1, y, z HTAB O25 S16_$1 HTAB O25 O32_$1 HTAB C9 O32_$1 EQIV $2 -x-2, y-1/2, -z+1/2 HTAB C24 S16_$2 HTAB C24 O32_$2 REM Highest difference peak 0.207, deepest hole -0.275, 1-sigma level 0.042 Q1 1 -1.4552 0.9345 0.1362 11.00000 0.05 0.21 Q2 1 -1.0782 0.8602 0.0461 11.00000 0.05 0.19 Q3 1 -1.4586 0.8155 -0.0347 11.00000 0.05 0.19 Q4 1 -1.1815 0.9014 0.0846 11.00000 0.05 0.17 Q5 1 -1.0999 0.8377 -0.0431 11.00000 0.05 0.17 REM The information below was added by Olex2. REM REM R1 = 0.0371 for 4267 Fo > 4sig(Fo) and 0.0419 for all 12131 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.21, deepest hole -0.27 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0419 REM R1_gt = 0.0371 REM wR_ref = 0.0865 REM GOOF = 1.054 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 12131 REM Reflections_gt = 4267 REM Parameters = n/a REM Hole = -0.27 REM Peak = 0.21 REM Flack = -0.00(4) ; _cod_data_source_file d1ob00784j2.cif _cod_data_source_block wdh1062 _cod_database_code 7158158 _chemical_oxdiff_formula 'C25 H21 N3 O2 S1' _chemical_oxdiff_usercomment 'RV-34-A t18' _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. ; _reflns_odcompleteness_completeness 99.81 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Riding coordinates: O25(H25) 2.b Ternary CH refined with riding coordinates: C23(H23) 2.c Aromatic/amide H refined with riding coordinates: C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31) 2.d Idealised Me refined as rotating group: C24(H24A,H24B,H24C) ; _shelx_shelxl_version_number 2014/7 _olex2_date_sample_data_collection 2016-02-25 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.174 _oxdiff_exptl_absorpt_empirical_full_min 0.863 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -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 S16 S -1.16626(9) 0.92396(4) 0.13067(3) 0.01862(15) Uani 1 1 d . . . . . O25 O -0.6694(3) 0.86782(13) 0.18145(9) 0.0295(5) Uani 1 1 d . . . . . H25 H -0.5579 0.8881 0.1743 0.044 Uiso 1 1 d R . . . . O32 O -1.3672(3) 0.95719(12) 0.14543(9) 0.0254(4) Uani 1 1 d . . . . . N11 N -1.0331(3) 0.72207(13) 0.22575(10) 0.0207(5) Uani 1 1 d . . . . . N14 N -1.2175(3) 0.74855(15) 0.14579(10) 0.0248(5) Uani 1 1 d . . . . . N15 N -1.1522(4) 0.68690(14) 0.18160(10) 0.0260(5) Uani 1 1 d . . . . . C1 C -0.9097(4) 0.86393(16) 0.26028(12) 0.0175(5) Uani 1 1 d . . . . . C2 C -0.9838(4) 0.88901(16) 0.32054(12) 0.0187(5) Uani 1 1 d . . . . . C3 C -1.1714(4) 0.86375(16) 0.34213(12) 0.0220(6) Uani 1 1 d . . . . . H3 H -1.2506 0.8281 0.3164 0.026 Uiso 1 1 calc R . . . . C4 C -1.2386(4) 0.8906(2) 0.39982(14) 0.0290(7) Uani 1 1 d . . . . . H4 H -1.3644 0.8732 0.4137 0.035 Uiso 1 1 calc R . . . . C5 C -1.1252(5) 0.94344(19) 0.43876(13) 0.0321(7) Uani 1 1 d . . . . . H5 H -1.1736 0.9614 0.4787 0.039 Uiso 1 1 calc R . . . . C6 C -0.9442(5) 0.96882(19) 0.41873(14) 0.0294(7) Uani 1 1 d . . . . . H6 H -0.8675 1.0045 0.4452 0.035 Uiso 1 1 calc R . . . . C7 C -0.8692(4) 0.94282(16) 0.35928(12) 0.0228(6) Uani 1 1 d . . . . . C8 C -0.6854(4) 0.97061(18) 0.33631(13) 0.0271(6) Uani 1 1 d . . . . . H8 H -0.6071 1.0064 0.3622 0.033 Uiso 1 1 calc R . . . . C9 C -0.6183(4) 0.94749(17) 0.27831(14) 0.0264(6) Uani 1 1 d . . . . . H9 H -0.4953 0.9677 0.2639 0.032 Uiso 1 1 calc R . . . . C10 C -0.7312(4) 0.89342(18) 0.23933(13) 0.0217(6) Uani 1 1 d . . . . . C12 C -1.0229(4) 0.80775(16) 0.21852(12) 0.0184(5) Uani 1 1 d . . . . . C13 C -1.1396(4) 0.82308(16) 0.16699(12) 0.0191(5) Uani 1 1 d . . . . . C17 C -1.1706(4) 0.88684(16) 0.05072(12) 0.0231(6) Uani 1 1 d . . . . . C18 C -0.9952(5) 0.8897(2) 0.01768(14) 0.0342(7) Uani 1 1 d . . . . . H18 H -0.8816 0.9130 0.0368 0.041 Uiso 1 1 calc R . . . . C19 C -0.9884(7) 0.8585(2) -0.04289(16) 0.0497(10) Uani 1 1 d . . . . . H19 H -0.8693 0.8592 -0.0659 0.060 Uiso 1 1 calc R . . . . C20 C -1.1541(8) 0.8262(2) -0.06999(15) 0.0582(12) Uani 1 1 d . . . . . H20 H -1.1480 0.8037 -0.1117 0.070 Uiso 1 1 calc R . . . . C21 C -1.3307(7) 0.8258(2) -0.03793(16) 0.0531(11) Uani 1 1 d . . . . . H21 H -1.4448 0.8045 -0.0580 0.064 Uiso 1 1 calc R . . . . C22 C -1.3406(5) 0.85680(18) 0.02429(14) 0.0334(7) Uani 1 1 d . . . . . H22 H -1.4599 0.8570 0.0472 0.040 Uiso 1 1 calc R . . . . C23 C -0.9164(4) 0.66965(17) 0.27010(13) 0.0237(6) Uani 1 1 d . . . . . H23 H -0.7901 0.7001 0.2775 0.028 Uiso 1 1 calc R . . . . C24 C -0.8684(5) 0.58410(18) 0.24001(14) 0.0342(7) Uani 1 1 d . . . . . H24A H -0.9887 0.5511 0.2346 0.051 Uiso 1 1 calc GR . . . . H24B H -0.7781 0.5527 0.2674 0.051 Uiso 1 1 calc GR . . . . H24C H -0.8073 0.5934 0.1986 0.051 Uiso 1 1 calc GR . . . . C26 C -1.0164(4) 0.66012(17) 0.33365(13) 0.0253(6) Uani 1 1 d . . . . . C27 C -1.2019(5) 0.62503(19) 0.33840(15) 0.0338(7) Uani 1 1 d . . . . . H27 H -1.2693 0.6075 0.3013 0.041 Uiso 1 1 calc R . . . . C28 C -1.2891(6) 0.6155(2) 0.39736(18) 0.0483(9) Uani 1 1 d . . . . . H28 H -1.4152 0.5907 0.4007 0.058 Uiso 1 1 calc R . . . . C29 C -1.1917(7) 0.6425(2) 0.45145(17) 0.0547(11) Uani 1 1 d . . . . . H29 H -1.2528 0.6375 0.4917 0.066 Uiso 1 1 calc R . . . . C30 C -1.0066(7) 0.6764(2) 0.44680(16) 0.0507(10) Uani 1 1 d . . . . . H30 H -0.9386 0.6935 0.4839 0.061 Uiso 1 1 calc R . . . . C31 C -0.9201(5) 0.6854(2) 0.38816(14) 0.0361(7) Uani 1 1 d . . . . . H31 H -0.7929 0.7093 0.3852 0.043 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 S16 0.0210(3) 0.0168(3) 0.0180(3) 0.0009(3) 0.0005(3) -0.0012(3) O25 0.0251(9) 0.0363(11) 0.0271(11) -0.0095(9) 0.0078(9) -0.0077(10) O32 0.0241(10) 0.0242(10) 0.0279(10) 0.0010(8) 0.0045(8) 0.0030(8) N11 0.0287(12) 0.0164(11) 0.0170(11) 0.0010(9) -0.0016(9) -0.0011(10) N14 0.0339(12) 0.0198(12) 0.0207(12) 0.0014(10) -0.0030(9) -0.0038(10) N15 0.0377(13) 0.0192(11) 0.0211(11) -0.0004(9) -0.0055(11) -0.0047(11) C1 0.0209(12) 0.0146(12) 0.0170(12) 0.0005(10) -0.0036(10) 0.0016(10) C2 0.0239(12) 0.0141(12) 0.0181(13) 0.0017(10) -0.0027(11) 0.0037(11) C3 0.0285(13) 0.0171(12) 0.0206(13) 0.0003(10) 0.0008(12) -0.0011(12) C4 0.0317(15) 0.0303(16) 0.0248(15) 0.0026(13) 0.0073(12) 0.0036(13) C5 0.0439(18) 0.0326(17) 0.0198(14) -0.0058(12) 0.0058(13) 0.0076(14) C6 0.0419(18) 0.0246(15) 0.0217(14) -0.0072(12) -0.0060(13) 0.0034(14) C7 0.0292(14) 0.0182(13) 0.0211(13) -0.0002(10) -0.0054(11) 0.0043(11) C8 0.0286(14) 0.0244(14) 0.0283(15) -0.0074(12) -0.0086(13) -0.0007(13) C9 0.0217(14) 0.0255(15) 0.0320(15) -0.0017(12) -0.0003(11) -0.0033(11) C10 0.0244(13) 0.0201(13) 0.0207(13) -0.0025(11) -0.0013(11) 0.0025(11) C12 0.0235(13) 0.0153(12) 0.0165(12) -0.0007(10) 0.0026(11) -0.0002(11) C13 0.0220(13) 0.0174(12) 0.0180(12) -0.0003(10) 0.0010(10) -0.0022(11) C17 0.0374(14) 0.0163(12) 0.0157(12) 0.0044(10) 0.0003(13) 0.0044(13) C18 0.0483(18) 0.0276(15) 0.0267(16) 0.0067(13) 0.0115(14) 0.0107(15) C19 0.090(3) 0.0331(19) 0.0258(17) 0.0037(15) 0.020(2) 0.020(2) C20 0.133(4) 0.0232(17) 0.0189(15) 0.0029(13) 0.010(2) 0.021(2) C21 0.102(3) 0.0229(17) 0.0348(19) 0.0035(14) -0.034(2) 0.000(2) C22 0.0517(18) 0.0237(15) 0.0246(14) 0.0060(12) -0.0113(15) -0.0029(15) C23 0.0310(14) 0.0186(13) 0.0215(14) 0.0025(11) -0.0032(11) 0.0012(12) C24 0.0525(19) 0.0217(14) 0.0286(15) 0.0047(13) 0.0037(14) 0.0106(15) C26 0.0382(16) 0.0166(13) 0.0210(14) 0.0034(11) -0.0016(13) 0.0033(13) C27 0.0414(18) 0.0255(16) 0.0346(17) 0.0013(13) 0.0024(14) -0.0029(14) C28 0.060(2) 0.0349(19) 0.050(2) 0.0113(17) 0.0229(19) -0.0017(17) C29 0.089(3) 0.047(2) 0.0286(18) 0.0112(16) 0.019(2) 0.004(2) C30 0.081(3) 0.046(2) 0.0247(17) 0.0055(16) -0.0105(19) 0.007(2) C31 0.0509(19) 0.0305(16) 0.0268(15) 0.0040(13) -0.0085(14) 0.0033(15) 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 _geom_angle_publ_flag O32 S16 C13 108.37(11) . . ? O32 S16 C17 107.09(12) . . ? C13 S16 C17 96.86(12) . . ? C10 O25 H25 109.5 . . ? N15 N11 C23 122.2(2) . . ? C12 N11 N15 111.0(2) . . ? C12 N11 C23 126.5(2) . . ? N15 N14 C13 108.2(2) . . ? N14 N15 N11 107.6(2) . . ? C2 C1 C12 121.0(2) . . ? C10 C1 C2 120.6(2) . . ? C10 C1 C12 118.4(2) . . ? C3 C2 C1 122.1(2) . . ? C7 C2 C1 119.0(2) . . ? C7 C2 C3 118.9(2) . . ? C2 C3 H3 119.9 . . ? C4 C3 C2 120.3(3) . . ? C4 C3 H3 119.9 . . ? C3 C4 H4 119.4 . . ? C3 C4 C5 121.2(3) . . ? C5 C4 H4 119.4 . . ? C4 C5 H5 120.3 . . ? C6 C5 C4 119.5(3) . . ? C6 C5 H5 120.3 . . ? C5 C6 H6 119.4 . . ? C5 C6 C7 121.2(3) . . ? C7 C6 H6 119.4 . . ? C2 C7 C6 119.0(3) . . ? C2 C7 C8 118.6(2) . . ? C6 C7 C8 122.4(3) . . ? C7 C8 H8 119.1 . . ? C9 C8 C7 121.8(3) . . ? C9 C8 H8 119.1 . . ? C8 C9 H9 120.0 . . ? C8 C9 C10 120.1(3) . . ? C10 C9 H9 120.0 . . ? O25 C10 C1 117.8(2) . . ? O25 C10 C9 122.2(2) . . ? C1 C10 C9 119.9(2) . . ? N11 C12 C1 123.8(2) . . ? N11 C12 C13 103.5(2) . . ? C13 C12 C1 132.7(2) . . ? N14 C13 S16 125.89(19) . . ? N14 C13 C12 109.8(2) . . ? C12 C13 S16 124.2(2) . . ? C18 C17 S16 116.7(2) . . ? C22 C17 S16 120.7(2) . . ? C22 C17 C18 122.6(3) . . ? C17 C18 H18 120.4 . . ? C19 C18 C17 119.1(3) . . ? C19 C18 H18 120.4 . . ? C18 C19 H19 120.2 . . ? C20 C19 C18 119.7(4) . . ? C20 C19 H19 120.2 . . ? C19 C20 H20 119.3 . . ? C19 C20 C21 121.4(3) . . ? C21 C20 H20 119.3 . . ? C20 C21 H21 120.1 . . ? C20 C21 C22 119.8(4) . . ? C22 C21 H21 120.1 . . ? C17 C22 C21 117.3(4) . . ? C17 C22 H22 121.3 . . ? C21 C22 H22 121.3 . . ? N11 C23 H23 107.4 . . ? N11 C23 C24 110.1(2) . . ? N11 C23 C26 111.8(2) . . ? C24 C23 H23 107.4 . . ? C26 C23 H23 107.4 . . ? C26 C23 C24 112.4(2) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C27 C26 C23 121.1(3) . . ? C31 C26 C23 119.6(3) . . ? C31 C26 C27 119.3(3) . . ? C26 C27 H27 120.0 . . ? C26 C27 C28 120.0(3) . . ? C28 C27 H27 120.0 . . ? C27 C28 H28 120.0 . . ? C29 C28 C27 119.9(3) . . ? C29 C28 H28 120.0 . . ? C28 C29 H29 120.0 . . ? C30 C29 C28 120.0(3) . . ? C30 C29 H29 120.0 . . ? C29 C30 H30 120.1 . . ? C29 C30 C31 119.9(3) . . ? C31 C30 H30 120.1 . . ? C26 C31 H31 119.6 . . ? C30 C31 C26 120.8(3) . . ? C30 C31 H31 119.6 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S16 O32 1.5038(19) . ? S16 C13 1.770(3) . ? S16 C17 1.787(3) . ? O25 H25 0.8402 . ? O25 C10 1.355(3) . ? N11 N15 1.356(3) . ? N11 C12 1.356(3) . ? N11 C23 1.481(3) . ? N14 N15 1.307(3) . ? N14 C13 1.362(3) . ? C1 C2 1.426(4) . ? C1 C10 1.380(4) . ? C1 C12 1.468(3) . ? C2 C3 1.419(4) . ? C2 C7 1.414(4) . ? C3 H3 0.9500 . ? C3 C4 1.369(4) . ? C4 H4 0.9500 . ? C4 C5 1.403(4) . ? C5 H5 0.9500 . ? C5 C6 1.368(4) . ? C6 H6 0.9500 . ? C6 C7 1.417(4) . ? C7 C8 1.418(4) . ? C8 H8 0.9500 . ? C8 C9 1.358(4) . ? C9 H9 0.9500 . ? C9 C10 1.413(4) . ? C12 C13 1.372(4) . ? C17 C18 1.389(4) . ? C17 C22 1.374(4) . ? C18 H18 0.9500 . ? C18 C19 1.371(4) . ? C19 H19 0.9500 . ? C19 C20 1.367(6) . ? C20 H20 0.9500 . ? C20 C21 1.386(7) . ? C21 H21 0.9500 . ? C21 C22 1.404(4) . ? C22 H22 0.9500 . ? C23 H23 1.0000 . ? C23 C24 1.522(4) . ? C23 C26 1.514(4) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C26 C27 1.388(4) . ? C26 C31 1.385(4) . ? C27 H27 0.9500 . ? C27 C28 1.389(4) . ? C28 H28 0.9500 . ? C28 C29 1.389(6) . ? C29 H29 0.9500 . ? C29 C30 1.378(6) . ? C30 H30 0.9500 . ? C30 C31 1.380(5) . ? C31 H31 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S16 C17 C18 C19 177.1(2) . . . . ? S16 C17 C22 C21 -177.6(2) . . . . ? O32 S16 C13 N14 76.7(3) . . . . ? O32 S16 C13 C12 -108.7(2) . . . . ? O32 S16 C17 C18 151.6(2) . . . . ? O32 S16 C17 C22 -28.7(2) . . . . ? N11 C12 C13 S16 -174.32(19) . . . . ? N11 C12 C13 N14 1.0(3) . . . . ? N11 C23 C26 C27 58.1(3) . . . . ? N11 C23 C26 C31 -123.0(3) . . . . ? N15 N11 C12 C1 178.3(2) . . . . ? N15 N11 C12 C13 -0.9(3) . . . . ? N15 N11 C23 C24 28.4(3) . . . . ? N15 N11 C23 C26 -97.3(3) . . . . ? N15 N14 C13 S16 174.4(2) . . . . ? N15 N14 C13 C12 -0.8(3) . . . . ? C1 C2 C3 C4 -178.7(3) . . . . ? C1 C2 C7 C6 179.0(2) . . . . ? C1 C2 C7 C8 0.7(4) . . . . ? C1 C12 C13 S16 6.6(4) . . . . ? C1 C12 C13 N14 -178.1(3) . . . . ? C2 C1 C10 O25 -179.5(2) . . . . ? C2 C1 C10 C9 1.4(4) . . . . ? C2 C1 C12 N11 -79.4(3) . . . . ? C2 C1 C12 C13 99.5(4) . . . . ? C2 C3 C4 C5 0.1(4) . . . . ? C2 C7 C8 C9 0.5(4) . . . . ? C3 C2 C7 C6 0.9(4) . . . . ? C3 C2 C7 C8 -177.5(2) . . . . ? C3 C4 C5 C6 0.2(5) . . . . ? C4 C5 C6 C7 0.1(4) . . . . ? C5 C6 C7 C2 -0.6(4) . . . . ? C5 C6 C7 C8 177.6(3) . . . . ? C6 C7 C8 C9 -177.7(3) . . . . ? C7 C2 C3 C4 -0.6(4) . . . . ? C7 C8 C9 C10 -0.8(4) . . . . ? C8 C9 C10 O25 -179.2(3) . . . . ? C8 C9 C10 C1 -0.1(4) . . . . ? C10 C1 C2 C3 176.4(2) . . . . ? C10 C1 C2 C7 -1.6(4) . . . . ? C10 C1 C12 N11 101.9(3) . . . . ? C10 C1 C12 C13 -79.2(4) . . . . ? C12 N11 N15 N14 0.5(3) . . . . ? C12 N11 C23 C24 -144.3(3) . . . . ? C12 N11 C23 C26 90.0(3) . . . . ? C12 C1 C2 C3 -2.2(4) . . . . ? C12 C1 C2 C7 179.7(2) . . . . ? C12 C1 C10 O25 -0.8(4) . . . . ? C12 C1 C10 C9 -179.9(2) . . . . ? C13 S16 C17 C18 -96.7(2) . . . . ? C13 S16 C17 C22 83.0(2) . . . . ? C13 N14 N15 N11 0.2(3) . . . . ? C17 S16 C13 N14 -33.9(3) . . . . ? C17 S16 C13 C12 140.7(2) . . . . ? C17 C18 C19 C20 0.9(5) . . . . ? C18 C17 C22 C21 2.0(4) . . . . ? C18 C19 C20 C21 1.2(5) . . . . ? C19 C20 C21 C22 -1.7(5) . . . . ? C20 C21 C22 C17 0.1(4) . . . . ? C22 C17 C18 C19 -2.6(4) . . . . ? C23 N11 N15 N14 -173.3(2) . . . . ? C23 N11 C12 C1 -8.3(4) . . . . ? C23 N11 C12 C13 172.5(2) . . . . ? C23 C26 C27 C28 178.8(3) . . . . ? C23 C26 C31 C30 -179.1(3) . . . . ? C24 C23 C26 C27 -66.2(3) . . . . ? C24 C23 C26 C31 112.6(3) . . . . ? C26 C27 C28 C29 1.0(5) . . . . ? C27 C26 C31 C30 -0.2(5) . . . . ? C27 C28 C29 C30 -1.8(6) . . . . ? C28 C29 C30 C31 1.6(6) . . . . ? C29 C30 C31 C26 -0.6(5) . . . . ? C31 C26 C27 C28 0.0(5) . . . . ?