#------------------------------------------------------------------------------ #$Date: 2021-07-06 06:56:22 +0300 (Tue, 06 Jul 2021) $ #$Revision: 267271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158159.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_7158159 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 geom _atom_sites_solution_primary direct _audit_creation_date 2016-03-01 _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 21.3972(3) _cell_length_b 14.6607(2) _cell_length_c 6.86195(11) _cell_measurement_reflns_used 7079 _cell_measurement_temperature 100(1) _cell_measurement_theta_max 28.5370 _cell_measurement_theta_min 3.2630 _cell_volume 2152.58(5) _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 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100(1) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 15.9631 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.996 _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 1.00 120.00 -- -17.00 -99.00-150.00 45 2 \w -90.00 27.00 1.00 120.00 -- -17.00 -19.00 30.00 117 3 \w -90.00 56.00 1.00 120.00 -- -17.00 0.00 90.00 146 4 \w -61.00 -36.00 1.00 120.00 -- -17.00 19.00-150.00 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 0.0058822000 _diffrn_orient_matrix_UB_12 -0.0415732000 _diffrn_orient_matrix_UB_13 0.0496586000 _diffrn_orient_matrix_UB_21 -0.0311400000 _diffrn_orient_matrix_UB_22 -0.0001069000 _diffrn_orient_matrix_UB_23 0.0353424000 _diffrn_orient_matrix_UB_31 -0.0097003000 _diffrn_orient_matrix_UB_32 -0.0247828000 _diffrn_orient_matrix_UB_33 -0.0834797000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_unetI/netI 0.0334 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 15539 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.368 _diffrn_reflns_theta_min 2.779 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.180 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.89221 _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 1.356 _exptl_crystal_description needle _exptl_crystal_F_000 920 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.188 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.043 _refine_ls_abs_structure_details ; Flack x determined using 1650 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.04(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 291 _refine_ls_number_reflns 4400 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.075 _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0318 _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^)+(0.0323P)^2^+0.4442P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0709 _refine_ls_wR_factor_ref 0.0723 _reflns_Friedel_coverage 0.741 _reflns_Friedel_fraction_full 0.999 _reflns_Friedel_fraction_max 0.999 _reflns_number_gt 4121 _reflns_number_total 4400 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; wdh1063.res created by SHELXL-2014/7 TITL WDH1063 in P212121 #19 REM reset to P212121 #19 CELL 0.71073 21.397174 14.660735 6.861955 90 90 90 ZERR 4 0.000255 0.000218 0.000109 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. 10 PLAN 10 TEMP -173.1(10) BOND HTAB MORE -1 BOND $H CONF fmap 2 acta SHEL 999 0.8 OMIT 0 14 0 OMIT 9 9 0 OMIT 16 0 4 OMIT 0 16 0 OMIT 12 0 3 OMIT 10 10 0 OMIT 9 12 0 OMIT 9 3 3 OMIT 0 12 0 REM REM REM WGHT 0.032300 0.444200 FVAR 1.86982 C1 1 -0.012159 0.912102 0.805421 11.00000 0.01180 0.00974 = 0.01450 -0.00210 0.00294 0.00058 C2 1 -0.071728 0.884269 0.731663 11.00000 0.01169 0.01203 = 0.01551 -0.00346 0.00256 0.00233 C3 1 -0.093390 0.908337 0.543894 11.00000 0.01407 0.01313 = 0.01777 -0.00287 0.00105 0.00122 AFIX 43 H3 2 -0.067959 0.944769 0.461311 11.00000 -1.20000 AFIX 0 C4 1 -0.150588 0.879616 0.480330 11.00000 0.01634 0.02177 = 0.01789 -0.00372 -0.00418 0.00276 AFIX 43 H4 2 -0.164677 0.896883 0.354331 11.00000 -1.20000 AFIX 0 C5 1 -0.188971 0.824781 0.598877 11.00000 0.01226 0.02072 = 0.02860 -0.00545 -0.00329 -0.00193 AFIX 43 H5 2 -0.228523 0.804853 0.552574 11.00000 -1.20000 AFIX 0 C6 1 -0.169181 0.800433 0.780114 11.00000 0.01389 0.01589 = 0.02615 -0.00055 0.00248 -0.00301 AFIX 43 H6 2 -0.195330 0.763633 0.859719 11.00000 -1.20000 AFIX 0 C7 1 -0.110259 0.829001 0.852186 11.00000 0.01273 0.01245 = 0.01821 -0.00372 0.00237 0.00094 C8 1 -0.088274 0.803239 1.038119 11.00000 0.01601 0.01347 = 0.01859 -0.00026 0.00578 -0.00064 AFIX 43 H8 2 -0.114239 0.767190 1.119850 11.00000 -1.20000 AFIX 0 C9 1 -0.030837 0.828747 1.103179 11.00000 0.01854 0.01476 = 0.01350 0.00021 -0.00003 0.00227 AFIX 43 H9 2 -0.016945 0.810167 1.228536 11.00000 -1.20000 AFIX 0 C10 1 0.008096 0.882900 0.984002 11.00000 0.01238 0.01330 = 0.01709 -0.00366 0.00110 0.00022 N11 3 0.027718 1.060809 0.663565 11.00000 0.01265 0.01169 = 0.01968 0.00196 0.00102 -0.00009 C12 1 0.030073 0.968894 0.685322 11.00000 0.01132 0.01231 = 0.01427 0.00037 -0.00272 -0.00111 C13 1 0.080199 0.943967 0.573328 11.00000 0.00945 0.01269 = 0.01753 0.00069 -0.00218 -0.00056 N14 3 0.105930 1.018693 0.487092 11.00000 0.01454 0.01352 = 0.02636 0.00276 0.00390 -0.00051 N15 3 0.073873 1.089802 0.542402 11.00000 0.01542 0.01445 = 0.02862 0.00416 0.00566 -0.00052 S16 5 0.109219 0.832012 0.547308 11.00000 0.01034 0.01218 = 0.01539 0.00049 -0.00058 -0.00022 C17 1 0.190373 0.859552 0.561272 11.00000 0.00927 0.01215 = 0.02487 -0.00326 -0.00003 0.00167 C18 1 0.218631 0.852211 0.742504 11.00000 0.01864 0.01790 = 0.02498 -0.00195 -0.00527 0.00235 AFIX 43 H18 2 0.196117 0.829784 0.851783 11.00000 -1.20000 AFIX 0 C19 1 0.280657 0.878502 0.759878 11.00000 0.02062 0.02302 = 0.03969 -0.00760 -0.01220 0.00229 AFIX 43 H19 2 0.300938 0.875127 0.882824 11.00000 -1.20000 AFIX 0 C20 1 0.312819 0.909405 0.599716 11.00000 0.01284 0.01890 = 0.05285 -0.01075 -0.00274 0.00076 AFIX 43 H20 2 0.355156 0.927834 0.613463 11.00000 -1.20000 AFIX 0 C21 1 0.284486 0.914127 0.418386 11.00000 0.01715 0.01937 = 0.04448 -0.00109 0.01142 0.00162 AFIX 43 H21 2 0.307466 0.934660 0.308352 11.00000 -1.20000 AFIX 0 C22 1 0.221989 0.888535 0.398392 11.00000 0.01728 0.01854 = 0.02506 -0.00076 0.00184 0.00302 AFIX 43 H22 2 0.201809 0.891094 0.275196 11.00000 -1.20000 AFIX 0 C23 1 -0.010558 1.131510 0.762753 11.00000 0.01603 0.01140 = 0.02802 -0.00194 0.00023 0.00262 AFIX 13 H23 2 0.002990 1.191666 0.708588 11.00000 -1.20000 AFIX 0 C24 1 0.005626 1.132800 0.979130 11.00000 0.02499 0.02589 = 0.03237 -0.00925 -0.00655 0.00796 AFIX 137 H24A 2 -0.001943 1.072316 1.035168 11.00000 -1.50000 H24B 2 -0.020532 1.177931 1.045811 11.00000 -1.50000 H24C 2 0.049753 1.148983 0.995485 11.00000 -1.50000 AFIX 0 O25 4 0.066030 0.908779 1.043740 11.00000 0.01417 0.02353 = 0.01849 0.00455 -0.00553 -0.00487 AFIX 147 H25 2 0.075043 0.881619 1.147798 11.00000 -1.50000 AFIX 0 C26 1 -0.079245 1.120937 0.711888 11.00000 0.01476 0.01230 = 0.02389 -0.00416 0.00085 0.00299 C27 1 -0.099103 1.148479 0.529167 11.00000 0.02099 0.01543 = 0.02140 0.00117 0.00325 0.00054 AFIX 43 H27 2 -0.069745 1.172785 0.439224 11.00000 -1.20000 AFIX 0 C28 1 -0.161691 1.140917 0.475838 11.00000 0.02460 0.02147 = 0.02814 0.00099 -0.00723 0.00541 AFIX 43 H28 2 -0.174853 1.159587 0.349777 11.00000 -1.20000 AFIX 0 C29 1 -0.204483 1.106272 0.606462 11.00000 0.01541 0.02185 = 0.04244 -0.00413 -0.00155 0.00444 AFIX 43 H29 2 -0.247197 1.100961 0.570433 11.00000 -1.20000 AFIX 0 C30 1 -0.185256 1.079279 0.789734 11.00000 0.01718 0.01837 = 0.03790 -0.00142 0.01152 0.00232 AFIX 43 H30 2 -0.214799 1.055325 0.879519 11.00000 -1.20000 AFIX 0 C31 1 -0.122726 1.087049 0.843368 11.00000 0.02187 0.01684 = 0.02289 -0.00160 0.00446 0.00310 AFIX 43 H31 2 -0.109802 1.069126 0.970160 11.00000 -1.20000 AFIX 0 O32 4 0.096877 0.802643 0.340354 11.00000 0.01854 0.01790 = 0.01843 -0.00261 -0.00401 0.00006 HKLF 4 REM WDH1063 in P212121 #19 REM R1 = 0.0318 for 4121 Fo > 4sig(Fo) and 0.0355 for all 4400 data REM 291 parameters refined using 0 restraints END WGHT 0.0323 0.4445 REM Instructions for potential hydrogen bonds EQIV $1 x, y, z+1 HTAB C9 O32_$1 EQIV $2 -x, y+1/2, -z+3/2 HTAB C24 S16_$2 HTAB C24 O32_$2 HTAB O25 S16_$1 HTAB O25 O32_$1 REM Highest difference peak 0.188, deepest hole -0.279, 1-sigma level 0.043 Q1 1 0.0942 0.8986 0.5819 11.00000 0.05 0.19 Q2 1 0.1796 0.7857 0.8316 11.00000 0.05 0.16 Q3 1 -0.0105 0.9169 0.9141 11.00000 0.05 0.15 Q4 1 -0.0576 1.0013 1.0631 11.00000 0.05 0.15 Q5 1 0.1024 0.7816 0.6568 11.00000 0.05 0.15 Q6 1 -0.0839 0.8385 0.7722 11.00000 0.05 0.15 Q7 1 -0.0887 1.2507 0.5813 11.00000 0.05 0.15 Q8 1 -0.0563 0.7980 1.0432 11.00000 0.05 0.14 Q9 1 0.0927 0.9658 0.5597 11.00000 0.05 0.14 Q10 1 -0.0922 0.8581 0.7948 11.00000 0.05 0.14 REM The information below was added by Olex2. REM REM R1 = 0.0318 for 4121 Fo > 4sig(Fo) and 0.0355 for all 16798 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.19, deepest hole -0.28 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0355 REM R1_gt = 0.0318 REM wR_ref = 0.0723 REM GOOF = 1.075 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 16798 REM Reflections_gt = 4121 REM Parameters = n/a REM Hole = -0.28 REM Peak = 0.19 REM Flack = -0.04(3) ; _cod_data_source_file d1ob00784j2.cif _cod_data_source_block wdh1063 _cod_database_code 7158159 _chemical_oxdiff_formula 'C26 H21 N3 S1 O2' _chemical_oxdiff_usercomment 'RV-33 t4 dia 1' _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 Ternary CH refined with riding coordinates: C23(H23) 2.b 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.c Idealised Me refined as rotating group: C24(H24A,H24B,H24C) 2.d Idealised tetrahedral OH refined as rotating group: O25(H25) ; _shelx_shelxl_version_number 2014/7 _olex2_date_sample_data_collection 2016-02-29 _olex2_submission_original_sample_id 'RV-33-A t4' _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 1.303 _oxdiff_exptl_absorpt_empirical_full_min 0.838 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 C1 C -0.01216(9) 0.91210(16) 0.8054(3) 0.0120(5) Uani 1 1 d . . . . . C2 C -0.07173(10) 0.88427(16) 0.7317(3) 0.0131(5) Uani 1 1 d . . . . . C3 C -0.09339(9) 0.90834(15) 0.5439(4) 0.0150(5) Uani 1 1 d . . . . . H3 H -0.0680 0.9448 0.4613 0.018 Uiso 1 1 calc R . . . . C4 C -0.15059(10) 0.87962(17) 0.4803(4) 0.0187(5) Uani 1 1 d . . . . . H4 H -0.1647 0.8969 0.3543 0.022 Uiso 1 1 calc R . . . . C5 C -0.18897(10) 0.82478(17) 0.5989(4) 0.0205(5) Uani 1 1 d . . . . . H5 H -0.2285 0.8049 0.5526 0.025 Uiso 1 1 calc R . . . . C6 C -0.16918(10) 0.80043(17) 0.7801(4) 0.0186(5) Uani 1 1 d . . . . . H6 H -0.1953 0.7636 0.8597 0.022 Uiso 1 1 calc R . . . . C7 C -0.11026(10) 0.82900(16) 0.8522(3) 0.0145(5) Uani 1 1 d . . . . . C8 C -0.08827(10) 0.80324(15) 1.0381(4) 0.0160(5) Uani 1 1 d . . . . . H8 H -0.1142 0.7672 1.1199 0.019 Uiso 1 1 calc R . . . . C9 C -0.03084(10) 0.82875(17) 1.1032(3) 0.0156(5) Uani 1 1 d . . . . . H9 H -0.0169 0.8102 1.2285 0.019 Uiso 1 1 calc R . . . . C10 C 0.00810(10) 0.88290(16) 0.9840(3) 0.0143(5) Uani 1 1 d . . . . . N11 N 0.02772(8) 1.06081(13) 0.6636(3) 0.0147(4) Uani 1 1 d . . . . . C12 C 0.03007(10) 0.96889(15) 0.6853(3) 0.0126(5) Uani 1 1 d . . . . . C13 C 0.08020(9) 0.94397(15) 0.5733(3) 0.0132(5) Uani 1 1 d . . . . . N14 N 0.10593(8) 1.01869(13) 0.4871(3) 0.0181(4) Uani 1 1 d . . . . . N15 N 0.07387(8) 1.08980(13) 0.5424(3) 0.0195(4) Uani 1 1 d . . . . . S16 S 0.10922(2) 0.83201(4) 0.54731(8) 0.01264(13) Uani 1 1 d . . . . . C17 C 0.19037(9) 0.85955(15) 0.5613(4) 0.0154(5) Uani 1 1 d . . . . . C18 C 0.21863(11) 0.85221(17) 0.7425(4) 0.0205(5) Uani 1 1 d . . . . . H18 H 0.1961 0.8298 0.8518 0.025 Uiso 1 1 calc R . . . . C19 C 0.28066(11) 0.87850(19) 0.7599(4) 0.0278(7) Uani 1 1 d . . . . . H19 H 0.3009 0.8751 0.8828 0.033 Uiso 1 1 calc R . . . . C20 C 0.31282(11) 0.90941(18) 0.5997(4) 0.0282(7) Uani 1 1 d . . . . . H20 H 0.3552 0.9278 0.6135 0.034 Uiso 1 1 calc R . . . . C21 C 0.28449(11) 0.91413(18) 0.4184(5) 0.0270(6) Uani 1 1 d . . . . . H21 H 0.3075 0.9347 0.3084 0.032 Uiso 1 1 calc R . . . . C22 C 0.22199(11) 0.88854(17) 0.3984(4) 0.0203(6) Uani 1 1 d . . . . . H22 H 0.2018 0.8911 0.2752 0.024 Uiso 1 1 calc R . . . . C23 C -0.01056(10) 1.13151(17) 0.7628(4) 0.0185(5) Uani 1 1 d . . . . . H23 H 0.0030 1.1917 0.7086 0.022 Uiso 1 1 calc R . . . . C24 C 0.00563(12) 1.13280(19) 0.9791(4) 0.0277(6) Uani 1 1 d . . . . . H24A H -0.0019 1.0723 1.0352 0.042 Uiso 1 1 calc GR . . . . H24B H -0.0205 1.1779 1.0458 0.042 Uiso 1 1 calc GR . . . . H24C H 0.0498 1.1490 0.9955 0.042 Uiso 1 1 calc GR . . . . O25 O 0.06603(7) 0.90878(11) 1.0437(3) 0.0187(4) Uani 1 1 d . . . . . H25 H 0.0750 0.8816 1.1478 0.028 Uiso 1 1 calc GR . . . . C26 C -0.07925(10) 1.12094(16) 0.7119(4) 0.0170(5) Uani 1 1 d . . . . . C27 C -0.09910(10) 1.14848(16) 0.5292(4) 0.0193(5) Uani 1 1 d . . . . . H27 H -0.0697 1.1728 0.4392 0.023 Uiso 1 1 calc R . . . . C28 C -0.16169(11) 1.14092(17) 0.4758(4) 0.0247(6) Uani 1 1 d . . . . . H28 H -0.1749 1.1596 0.3498 0.030 Uiso 1 1 calc R . . . . C29 C -0.20448(11) 1.10627(18) 0.6065(4) 0.0266(7) Uani 1 1 d . . . . . H29 H -0.2472 1.1010 0.5704 0.032 Uiso 1 1 calc R . . . . C30 C -0.18526(11) 1.07928(18) 0.7897(4) 0.0245(6) Uani 1 1 d . . . . . H30 H -0.2148 1.0553 0.8795 0.029 Uiso 1 1 calc R . . . . C31 C -0.12273(11) 1.08705(17) 0.8434(4) 0.0205(5) Uani 1 1 d . . . . . H31 H -0.1098 1.0691 0.9702 0.025 Uiso 1 1 calc R . . . . O32 O 0.09688(7) 0.80264(11) 0.3404(2) 0.0183(4) 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 0.0118(10) 0.0097(12) 0.0145(12) -0.0021(10) 0.0029(8) 0.0006(8) C2 0.0117(11) 0.0120(12) 0.0155(12) -0.0035(10) 0.0026(9) 0.0023(8) C3 0.0141(10) 0.0131(11) 0.0178(11) -0.0029(11) 0.0010(9) 0.0012(8) C4 0.0163(11) 0.0218(13) 0.0179(13) -0.0037(11) -0.0042(9) 0.0028(9) C5 0.0123(10) 0.0207(13) 0.0286(14) -0.0054(12) -0.0033(9) -0.0019(9) C6 0.0139(11) 0.0159(12) 0.0262(14) -0.0005(11) 0.0025(10) -0.0030(9) C7 0.0127(10) 0.0124(11) 0.0182(11) -0.0037(10) 0.0024(9) 0.0009(9) C8 0.0160(10) 0.0135(11) 0.0186(12) -0.0003(11) 0.0058(10) -0.0006(8) C9 0.0185(11) 0.0148(12) 0.0135(12) 0.0002(11) 0.0000(8) 0.0023(9) C10 0.0124(10) 0.0133(12) 0.0171(12) -0.0037(10) 0.0011(9) 0.0002(8) N11 0.0127(9) 0.0117(10) 0.0197(11) 0.0020(9) 0.0010(8) -0.0001(7) C12 0.0113(10) 0.0123(12) 0.0143(11) 0.0004(10) -0.0027(9) -0.0011(8) C13 0.0094(9) 0.0127(11) 0.0175(12) 0.0007(10) -0.0022(9) -0.0006(8) N14 0.0145(9) 0.0135(9) 0.0264(12) 0.0028(9) 0.0039(8) -0.0005(7) N15 0.0154(9) 0.0145(10) 0.0286(11) 0.0042(10) 0.0057(9) -0.0005(7) S16 0.0103(2) 0.0122(3) 0.0154(3) 0.0005(2) -0.0006(2) -0.0002(2) C17 0.0093(9) 0.0122(11) 0.0249(13) -0.0033(11) 0.0000(10) 0.0017(8) C18 0.0186(11) 0.0179(14) 0.0250(14) -0.0019(11) -0.0053(10) 0.0024(9) C19 0.0206(13) 0.0230(15) 0.0397(17) -0.0076(13) -0.0122(12) 0.0023(10) C20 0.0128(11) 0.0189(14) 0.053(2) -0.0108(14) -0.0027(11) 0.0008(10) C21 0.0172(11) 0.0194(13) 0.0445(18) -0.0011(13) 0.0114(12) 0.0016(10) C22 0.0173(11) 0.0185(13) 0.0251(14) -0.0008(11) 0.0018(10) 0.0030(9) C23 0.0160(11) 0.0114(12) 0.0280(14) -0.0019(11) 0.0002(10) 0.0026(9) C24 0.0250(13) 0.0259(15) 0.0324(16) -0.0093(13) -0.0066(11) 0.0080(10) O25 0.0142(7) 0.0235(10) 0.0185(9) 0.0045(8) -0.0055(7) -0.0049(6) C26 0.0148(11) 0.0123(12) 0.0239(13) -0.0042(11) 0.0008(10) 0.0030(8) C27 0.0210(11) 0.0154(12) 0.0214(13) 0.0012(11) 0.0033(10) 0.0005(9) C28 0.0246(12) 0.0215(13) 0.0281(14) 0.0010(12) -0.0072(11) 0.0054(10) C29 0.0154(12) 0.0218(14) 0.0424(18) -0.0041(13) -0.0015(11) 0.0044(10) C30 0.0172(12) 0.0184(13) 0.0379(16) -0.0014(13) 0.0115(11) 0.0023(10) C31 0.0219(12) 0.0168(13) 0.0229(13) -0.0016(11) 0.0045(10) 0.0031(10) O32 0.0185(8) 0.0179(9) 0.0184(9) -0.0026(8) -0.0040(6) 0.0001(6) 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 C2 C1 C12 120.5(2) . . ? C10 C1 C2 120.6(2) . . ? C10 C1 C12 118.78(19) . . ? C3 C2 C1 122.9(2) . . ? C3 C2 C7 118.8(2) . . ? C7 C2 C1 118.3(2) . . ? C2 C3 H3 119.7 . . ? C4 C3 C2 120.5(2) . . ? C4 C3 H3 119.7 . . ? C3 C4 H4 119.5 . . ? C3 C4 C5 120.9(2) . . ? C5 C4 H4 119.5 . . ? C4 C5 H5 120.1 . . ? C6 C5 C4 119.7(2) . . ? C6 C5 H5 120.1 . . ? C5 C6 H6 119.4 . . ? C5 C6 C7 121.2(2) . . ? C7 C6 H6 119.4 . . ? C6 C7 C2 118.8(2) . . ? C8 C7 C2 119.0(2) . . ? C8 C7 C6 122.2(2) . . ? C7 C8 H8 119.2 . . ? C9 C8 C7 121.6(2) . . ? C9 C8 H8 119.2 . . ? C8 C9 H9 120.1 . . ? C8 C9 C10 119.8(2) . . ? C10 C9 H9 120.1 . . ? C1 C10 C9 120.5(2) . . ? O25 C10 C1 118.1(2) . . ? O25 C10 C9 121.4(2) . . ? C12 N11 N15 110.55(19) . . ? C12 N11 C23 131.5(2) . . ? N15 N11 C23 117.55(19) . . ? N11 C12 C1 126.7(2) . . ? N11 C12 C13 103.4(2) . . ? C13 C12 C1 129.9(2) . . ? C12 C13 S16 125.52(18) . . ? N14 C13 C12 110.2(2) . . ? N14 C13 S16 124.22(16) . . ? N15 N14 C13 107.70(18) . . ? N14 N15 N11 108.07(18) . . ? C13 S16 C17 97.27(10) . . ? O32 S16 C13 107.43(10) . . ? O32 S16 C17 106.59(11) . . ? C18 C17 S16 117.04(18) . . ? C22 C17 S16 120.35(19) . . ? C22 C17 C18 122.6(2) . . ? C17 C18 H18 120.9 . . ? C17 C18 C19 118.2(2) . . ? C19 C18 H18 120.9 . . ? C18 C19 H19 119.9 . . ? C20 C19 C18 120.1(3) . . ? C20 C19 H19 119.9 . . ? C19 C20 H20 119.5 . . ? C19 C20 C21 121.0(2) . . ? C21 C20 H20 119.5 . . ? C20 C21 H21 120.2 . . ? C20 C21 C22 119.6(3) . . ? C22 C21 H21 120.2 . . ? C17 C22 C21 118.4(2) . . ? C17 C22 H22 120.8 . . ? C21 C22 H22 120.8 . . ? N11 C23 H23 106.6 . . ? N11 C23 C24 109.24(19) . . ? N11 C23 C26 110.9(2) . . ? C24 C23 H23 106.6 . . ? C26 C23 H23 106.6 . . ? C26 C23 C24 116.4(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 . . ? C10 O25 H25 109.5 . . ? C27 C26 C23 118.4(2) . . ? C27 C26 C31 119.2(2) . . ? C31 C26 C23 122.4(2) . . ? C26 C27 H27 119.7 . . ? C26 C27 C28 120.7(2) . . ? C28 C27 H27 119.7 . . ? C27 C28 H28 120.1 . . ? C29 C28 C27 119.8(2) . . ? C29 C28 H28 120.1 . . ? C28 C29 H29 120.0 . . ? C28 C29 C30 120.0(2) . . ? C30 C29 H29 120.0 . . ? C29 C30 H30 119.9 . . ? C29 C30 C31 120.2(2) . . ? C31 C30 H30 119.9 . . ? C26 C31 C30 120.1(2) . . ? C26 C31 H31 119.9 . . ? C30 C31 H31 119.9 . . ? 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 C1 C2 1.431(3) . ? C1 C10 1.368(3) . ? C1 C12 1.480(3) . ? C2 C3 1.414(3) . ? C2 C7 1.421(3) . ? C3 H3 0.9500 . ? C3 C4 1.366(3) . ? C4 H4 0.9500 . ? C4 C5 1.408(3) . ? C5 H5 0.9500 . ? C5 C6 1.361(3) . ? C6 H6 0.9500 . ? C6 C7 1.418(3) . ? C7 C8 1.411(3) . ? C8 H8 0.9500 . ? C8 C9 1.360(3) . ? C9 H9 0.9500 . ? C9 C10 1.412(3) . ? C10 O25 1.360(2) . ? N11 C12 1.357(3) . ? N11 N15 1.359(3) . ? N11 C23 1.486(3) . ? C12 C13 1.369(3) . ? C13 N14 1.361(3) . ? C13 S16 1.764(2) . ? N14 N15 1.304(3) . ? S16 C17 1.785(2) . ? S16 O32 1.5073(17) . ? C17 C18 1.387(3) . ? C17 C22 1.374(3) . ? C18 H18 0.9500 . ? C18 C19 1.387(3) . ? C19 H19 0.9500 . ? C19 C20 1.374(4) . ? C20 H20 0.9500 . ? C20 C21 1.386(4) . ? C21 H21 0.9500 . ? C21 C22 1.396(3) . ? C22 H22 0.9500 . ? C23 H23 1.0000 . ? C23 C24 1.525(4) . ? C23 C26 1.519(3) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? O25 H25 0.8400 . ? C26 C27 1.384(3) . ? C26 C31 1.388(3) . ? C27 H27 0.9500 . ? C27 C28 1.393(3) . ? C28 H28 0.9500 . ? C28 C29 1.378(4) . ? C29 H29 0.9500 . ? C29 C30 1.381(4) . ? C30 H30 0.9500 . ? C30 C31 1.392(3) . ? 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 C1 C2 C3 C4 179.7(2) . . . . ? C1 C2 C7 C6 -179.5(2) . . . . ? C1 C2 C7 C8 -0.5(3) . . . . ? C1 C12 C13 N14 -179.9(2) . . . . ? C1 C12 C13 S16 -1.4(4) . . . . ? C2 C1 C10 C9 -3.4(3) . . . . ? C2 C1 C10 O25 177.6(2) . . . . ? C2 C1 C12 N11 82.3(3) . . . . ? C2 C1 C12 C13 -98.5(3) . . . . ? C2 C3 C4 C5 -0.7(3) . . . . ? C2 C7 C8 C9 -1.1(3) . . . . ? C3 C2 C7 C6 -0.3(3) . . . . ? C3 C2 C7 C8 178.7(2) . . . . ? C3 C4 C5 C6 0.5(4) . . . . ? C4 C5 C6 C7 -0.3(4) . . . . ? C5 C6 C7 C2 0.2(3) . . . . ? C5 C6 C7 C8 -178.8(2) . . . . ? C6 C7 C8 C9 177.9(2) . . . . ? C7 C2 C3 C4 0.6(3) . . . . ? C7 C8 C9 C10 0.5(4) . . . . ? C8 C9 C10 C1 1.8(3) . . . . ? C8 C9 C10 O25 -179.3(2) . . . . ? C10 C1 C2 C3 -176.4(2) . . . . ? C10 C1 C2 C7 2.7(3) . . . . ? C10 C1 C12 N11 -100.9(3) . . . . ? C10 C1 C12 C13 78.2(3) . . . . ? N11 C12 C13 N14 -0.7(3) . . . . ? N11 C12 C13 S16 177.88(17) . . . . ? N11 C23 C26 C27 -75.1(3) . . . . ? N11 C23 C26 C31 106.7(3) . . . . ? C12 C1 C2 C3 0.2(3) . . . . ? C12 C1 C2 C7 179.4(2) . . . . ? C12 C1 C10 C9 179.9(2) . . . . ? C12 C1 C10 O25 0.9(3) . . . . ? C12 N11 N15 N14 -0.4(3) . . . . ? C12 N11 C23 C24 62.9(3) . . . . ? C12 N11 C23 C26 -66.7(3) . . . . ? C12 C13 N14 N15 0.4(3) . . . . ? C12 C13 S16 C17 -137.8(2) . . . . ? C12 C13 S16 O32 112.2(2) . . . . ? C13 N14 N15 N11 0.0(2) . . . . ? C13 S16 C17 C18 95.0(2) . . . . ? C13 S16 C17 C22 -83.6(2) . . . . ? N14 C13 S16 C17 40.6(2) . . . . ? N14 C13 S16 O32 -69.4(2) . . . . ? N15 N11 C12 C1 180.0(2) . . . . ? N15 N11 C12 C13 0.6(2) . . . . ? N15 N11 C23 C24 -109.1(2) . . . . ? N15 N11 C23 C26 121.2(2) . . . . ? S16 C13 N14 N15 -178.11(17) . . . . ? S16 C17 C18 C19 -176.14(19) . . . . ? S16 C17 C22 C21 176.51(18) . . . . ? C17 C18 C19 C20 -1.0(4) . . . . ? C18 C17 C22 C21 -2.0(4) . . . . ? C18 C19 C20 C21 -0.6(4) . . . . ? C19 C20 C21 C22 1.1(4) . . . . ? C20 C21 C22 C17 0.2(4) . . . . ? C22 C17 C18 C19 2.4(4) . . . . ? C23 N11 C12 C1 7.5(4) . . . . ? C23 N11 C12 C13 -171.9(2) . . . . ? C23 N11 N15 N14 173.28(19) . . . . ? C23 C26 C27 C28 -179.5(2) . . . . ? C23 C26 C31 C30 179.6(2) . . . . ? C24 C23 C26 C27 159.2(2) . . . . ? C24 C23 C26 C31 -19.0(3) . . . . ? C26 C27 C28 C29 0.5(4) . . . . ? C27 C26 C31 C30 1.3(4) . . . . ? C27 C28 C29 C30 0.1(4) . . . . ? C28 C29 C30 C31 0.1(4) . . . . ? C29 C30 C31 C26 -0.8(4) . . . . ? C31 C26 C27 C28 -1.1(4) . . . . ? O32 S16 C17 C18 -154.30(18) . . . . ? O32 S16 C17 C22 27.1(2) . . . . ?