#------------------------------------------------------------------------------ #$Date: 2021-07-06 06:56:22 +0300 (Tue, 06 Jul 2021) $ #$Revision: 267271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158160.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_7158160 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 2016-03-03 _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 8.2288(5) _cell_length_b 10.1233(6) _cell_length_c 25.6942(15) _cell_measurement_reflns_used 4553 _cell_measurement_temperature 100.01(10) _cell_measurement_theta_max 26.2550 _cell_measurement_theta_min 2.9010 _cell_volume 2140.4(2) _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 100.01(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 -54.00 63.00 1.00 150.00 -- 19.03 -19.00-180.00 117 2 \w -6.00 91.00 1.00 150.00 -- 19.03 38.00 30.00 97 3 \w -87.00 13.00 1.00 150.00 -- -17.00 -77.00-150.00 100 4 \w 34.00 96.00 1.00 150.00 -- 19.03-178.00-150.00 62 5 \w -2.00 25.00 1.00 150.00 -- 19.03 57.00 150.00 27 6 \w 34.00 96.00 1.00 150.00 -- 19.03-178.00 120.00 62 ; _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 -0.0215187000 _diffrn_orient_matrix_UB_12 0.0392788000 _diffrn_orient_matrix_UB_13 0.0217870000 _diffrn_orient_matrix_UB_21 0.0831130000 _diffrn_orient_matrix_UB_22 0.0049904000 _diffrn_orient_matrix_UB_23 0.0070352000 _diffrn_orient_matrix_UB_31 0.0074783000 _diffrn_orient_matrix_UB_32 0.0578614000 _diffrn_orient_matrix_UB_33 -0.0154026000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0624 _diffrn_reflns_av_unetI/netI 0.0648 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 19890 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.371 _diffrn_reflns_theta_min 2.562 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.181 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.84723 _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 1.364 _exptl_crystal_description needle _exptl_crystal_F_000 920 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.245 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.051 _refine_ls_abs_structure_details ; Flack x determined using 1245 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.02(6) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 291 _refine_ls_number_reflns 4376 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.042 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0464 _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^)+(0.0325P)^2^+0.2326P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0820 _refine_ls_wR_factor_ref 0.0873 _reflns_Friedel_coverage 0.741 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 1.000 _reflns_number_gt 3615 _reflns_number_total 4376 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; wdh1064.res created by SHELXL-2014/7 TITL WDH1064 in P212121 #19 REM reset to P212121 #19 CELL 0.71073 8.228835 10.123337 25.694247 90 90 90 ZERR 4 0.000519 0.000577 0.001458 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 HTAB MORE -1 BOND $H CONF fmap 2 acta SHEL 999 0.8 OMIT 0 4 12 OMIT 0 3 9 OMIT 6 6 0 OMIT 4 8 0 REM REM REM WGHT 0.032500 0.232600 FVAR 0.89230 C1 1 0.932081 0.240398 0.595709 11.00000 0.01106 0.01162 = 0.01611 -0.00259 0.00173 -0.00357 C2 1 0.947543 0.204965 0.544097 11.00000 0.01120 0.01571 = 0.01736 0.00045 -0.00096 -0.00563 C3 1 1.043335 0.094723 0.529822 11.00000 0.01681 0.02054 = 0.02028 -0.00846 0.00158 -0.00225 AFIX 43 H3 2 1.051679 0.069863 0.494270 11.00000 -1.20000 AFIX 0 C4 1 1.123413 0.024315 0.566801 11.00000 0.01613 0.01749 = 0.02782 -0.00658 0.00193 0.00135 AFIX 43 H4 2 1.190089 -0.047711 0.556518 11.00000 -1.20000 AFIX 0 C5 1 1.109806 0.055809 0.620382 11.00000 0.01507 0.01497 = 0.02536 0.00027 0.00085 -0.00288 C6 1 1.194915 -0.015290 0.659225 11.00000 0.01825 0.01575 = 0.03965 0.00148 -0.00440 -0.00209 AFIX 43 H6 2 1.263677 -0.086373 0.649341 11.00000 -1.20000 AFIX 0 C7 1 1.179913 0.016477 0.710575 11.00000 0.02437 0.01979 = 0.03112 0.01105 -0.01091 -0.00480 AFIX 43 H7 2 1.237236 -0.032738 0.736148 11.00000 -1.20000 AFIX 0 C8 1 1.079262 0.122414 0.725661 11.00000 0.02310 0.02776 = 0.02066 0.00556 0.00042 -0.01082 AFIX 43 H8 2 1.068135 0.143551 0.761507 11.00000 -1.20000 AFIX 0 C9 1 0.997125 0.195387 0.689103 11.00000 0.01325 0.01813 = 0.02101 0.00265 0.00208 -0.00294 AFIX 43 H9 2 0.930201 0.266717 0.699959 11.00000 -1.20000 AFIX 0 C10 1 1.010906 0.165626 0.635265 11.00000 0.01456 0.01155 = 0.01916 -0.00022 -0.00018 -0.00523 N11 3 0.894855 0.484567 0.608386 11.00000 0.01631 0.01456 = 0.01580 -0.00027 0.00440 0.00192 C12 1 0.835477 0.359099 0.608634 11.00000 0.01955 0.01403 = 0.00711 -0.00052 -0.00027 0.00037 C13 1 0.676128 0.376796 0.623167 11.00000 0.01614 0.01696 = 0.01238 0.00086 0.00360 -0.00038 N14 3 0.644653 0.507980 0.631242 11.00000 0.01750 0.01805 = 0.01967 0.00012 0.00393 0.00009 N15 3 0.779680 0.573873 0.621925 11.00000 0.01968 0.01527 = 0.02373 0.00011 0.00650 0.00430 S16 5 0.523530 0.255271 0.626431 11.00000 0.01687 0.01855 = 0.01619 -0.00487 0.00345 -0.00303 C17 1 0.455645 0.289068 0.691289 11.00000 0.01466 0.01492 = 0.01517 -0.00265 0.00238 -0.00396 C18 1 0.336184 0.382663 0.699507 11.00000 0.01710 0.02063 = 0.01625 0.00324 -0.00092 -0.00290 AFIX 43 H18 2 0.291445 0.430713 0.671164 11.00000 -1.20000 AFIX 0 C19 1 0.282696 0.405169 0.750081 11.00000 0.01639 0.02199 = 0.02111 -0.00383 0.00241 -0.00115 AFIX 43 H19 2 0.200663 0.469158 0.756501 11.00000 -1.20000 AFIX 0 C20 1 0.348314 0.334973 0.790842 11.00000 0.02400 0.03378 = 0.01177 -0.00383 0.00301 -0.00892 AFIX 43 H20 2 0.311131 0.350548 0.825303 11.00000 -1.20000 AFIX 0 C21 1 0.468368 0.241663 0.781893 11.00000 0.02677 0.03048 = 0.01787 0.00862 -0.00547 -0.00339 AFIX 43 H21 2 0.513698 0.193943 0.810226 11.00000 -1.20000 AFIX 0 C22 1 0.522271 0.217926 0.731767 11.00000 0.01555 0.02013 = 0.02506 0.00493 -0.00099 0.00111 AFIX 43 H22 2 0.603913 0.153618 0.725332 11.00000 -1.20000 AFIX 0 C23 1 1.056313 0.532005 0.591194 11.00000 0.01182 0.01600 = 0.01767 0.00015 0.00324 0.00050 AFIX 13 H23 2 1.132904 0.455330 0.591843 11.00000 -1.20000 AFIX 0 C24 1 1.119639 0.635759 0.629059 11.00000 0.02157 0.01980 = 0.01823 -0.00111 -0.00007 -0.00354 AFIX 137 H24A 2 1.050386 0.714402 0.627397 11.00000 -1.50000 H24B 2 1.231233 0.659688 0.619649 11.00000 -1.50000 H24C 2 1.118031 0.599924 0.664487 11.00000 -1.50000 AFIX 0 O25 4 0.866231 0.279102 0.508752 11.00000 0.02198 0.02347 = 0.01166 -0.00295 -0.00024 0.00327 AFIX 147 H25 2 0.893127 0.255845 0.478575 11.00000 -1.50000 AFIX 0 C26 1 1.047893 0.583309 0.535510 11.00000 0.01155 0.01544 = 0.01495 -0.00077 0.00199 -0.00517 C27 1 1.127411 0.516323 0.496094 11.00000 0.02038 0.01663 = 0.02337 -0.00141 0.00664 0.00038 AFIX 43 H27 2 1.182615 0.436141 0.503608 11.00000 -1.20000 AFIX 0 C28 1 1.127149 0.565402 0.445628 11.00000 0.02388 0.02406 = 0.01948 -0.00640 0.00671 -0.00545 AFIX 43 H28 2 1.182161 0.518943 0.418766 11.00000 -1.20000 AFIX 0 C29 1 1.046594 0.682161 0.434497 11.00000 0.02384 0.02661 = 0.01430 0.00094 0.00029 -0.00842 AFIX 43 H29 2 1.046892 0.716021 0.400015 11.00000 -1.20000 AFIX 0 C30 1 0.965544 0.749681 0.473596 11.00000 0.02119 0.01978 = 0.02051 0.00354 -0.00236 -0.00246 AFIX 43 H30 2 0.910031 0.829643 0.465953 11.00000 -1.20000 AFIX 0 C31 1 0.965768 0.699927 0.524096 11.00000 0.01673 0.01974 = 0.01789 -0.00094 0.00164 0.00044 AFIX 43 H31 2 0.909624 0.745771 0.550882 11.00000 -1.20000 AFIX 0 O32 4 0.390965 0.301498 0.590396 11.00000 0.01964 0.03770 = 0.01199 -0.00493 -0.00069 -0.00339 HKLF 4 REM WDH1064 in P212121 #19 REM R1 = 0.0464 for 3615 Fo > 4sig(Fo) and 0.0622 for all 4376 data REM 291 parameters refined using 0 restraints END WGHT 0.0325 0.2326 REM Instructions for potential hydrogen bonds EQIV $1 x+1, y, z HTAB C23 O32_$1 EQIV $2 x+1/2, -y+1/2, -z+1 HTAB O25 S16_$2 HTAB O25 O32_$2 REM Highest difference peak 0.245, deepest hole -0.261, 1-sigma level 0.051 Q1 1 0.4831 0.2743 0.6651 11.00000 0.05 0.25 Q2 1 0.5598 0.1568 0.6220 11.00000 0.05 0.24 Q3 1 1.3518 -0.0191 0.6245 11.00000 0.05 0.21 Q4 1 0.4419 0.3543 0.6955 11.00000 0.05 0.21 Q5 1 0.4751 0.1326 0.8006 11.00000 0.05 0.20 REM The information below was added by Olex2. REM REM R1 = 0.0464 for 3615 Fo > 4sig(Fo) and 0.0622 for all 21415 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.25, deepest hole -0.26 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0622 REM R1_gt = 0.0464 REM wR_ref = 0.0873 REM GOOF = 1.042 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 21415 REM Reflections_gt = 3615 REM Parameters = n/a REM Hole = -0.26 REM Peak = 0.25 REM Flack = -0.02(6) ; _cod_data_source_file d1ob00784j2.cif _cod_data_source_block wdh1064 _cod_database_code 7158160 _chemical_oxdiff_formula 'C26 H21 N3 S1 O2' _chemical_oxdiff_usercomment 'RV-33B t10 dia 2' _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 99.84 _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), C6(H6), C7(H7), 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 2016-03-01 _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 1.181 _oxdiff_exptl_absorpt_empirical_full_min 0.766 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 0.9321(4) 0.2404(3) 0.59571(12) 0.0129(7) Uani 1 1 d . . . . . C2 C 0.9475(4) 0.2050(3) 0.54410(12) 0.0148(8) Uani 1 1 d . . . . . C3 C 1.0433(4) 0.0947(3) 0.52982(14) 0.0192(8) Uani 1 1 d . . . . . H3 H 1.0517 0.0699 0.4943 0.023 Uiso 1 1 calc R . . . . C4 C 1.1234(4) 0.0243(3) 0.56680(14) 0.0205(8) Uani 1 1 d . . . . . H4 H 1.1901 -0.0477 0.5565 0.025 Uiso 1 1 calc R . . . . C5 C 1.1098(4) 0.0558(3) 0.62038(14) 0.0185(8) Uani 1 1 d . . . . . C6 C 1.1949(5) -0.0153(3) 0.65923(15) 0.0246(9) Uani 1 1 d . . . . . H6 H 1.2637 -0.0864 0.6493 0.029 Uiso 1 1 calc R . . . . C7 C 1.1799(5) 0.0165(3) 0.71057(14) 0.0251(9) Uani 1 1 d . . . . . H7 H 1.2372 -0.0327 0.7361 0.030 Uiso 1 1 calc R . . . . C8 C 1.0793(4) 0.1224(3) 0.72566(14) 0.0238(9) Uani 1 1 d . . . . . H8 H 1.0681 0.1436 0.7615 0.029 Uiso 1 1 calc R . . . . C9 C 0.9971(4) 0.1954(3) 0.68910(12) 0.0175(8) Uani 1 1 d . . . . . H9 H 0.9302 0.2667 0.7000 0.021 Uiso 1 1 calc R . . . . C10 C 1.0109(4) 0.1656(3) 0.63527(12) 0.0151(7) Uani 1 1 d . . . . . N11 N 0.8949(3) 0.4846(3) 0.60839(10) 0.0156(6) Uani 1 1 d . . . . . C12 C 0.8355(4) 0.3591(3) 0.60863(12) 0.0136(7) Uani 1 1 d . . . . . C13 C 0.6761(4) 0.3768(3) 0.62317(13) 0.0152(7) Uani 1 1 d . . . . . N14 N 0.6447(3) 0.5080(3) 0.63124(11) 0.0184(7) Uani 1 1 d . . . . . N15 N 0.7797(3) 0.5739(3) 0.62193(11) 0.0196(7) Uani 1 1 d . . . . . S16 S 0.52353(10) 0.25527(8) 0.62643(3) 0.0172(2) Uani 1 1 d . . . . . C17 C 0.4556(4) 0.2891(3) 0.69129(12) 0.0149(7) Uani 1 1 d . . . . . C18 C 0.3362(4) 0.3827(3) 0.69951(13) 0.0180(8) Uani 1 1 d . . . . . H18 H 0.2914 0.4307 0.6712 0.022 Uiso 1 1 calc R . . . . C19 C 0.2827(4) 0.4052(3) 0.75008(13) 0.0198(8) Uani 1 1 d . . . . . H19 H 0.2007 0.4692 0.7565 0.024 Uiso 1 1 calc R . . . . C20 C 0.3483(4) 0.3350(4) 0.79084(13) 0.0232(9) Uani 1 1 d . . . . . H20 H 0.3111 0.3505 0.8253 0.028 Uiso 1 1 calc R . . . . C21 C 0.4684(4) 0.2417(4) 0.78189(12) 0.0250(8) Uani 1 1 d . . . . . H21 H 0.5137 0.1939 0.8102 0.030 Uiso 1 1 calc R . . . . C22 C 0.5223(4) 0.2179(3) 0.73177(13) 0.0202(8) Uani 1 1 d . . . . . H22 H 0.6039 0.1536 0.7253 0.024 Uiso 1 1 calc R . . . . C23 C 1.0563(4) 0.5320(3) 0.59119(13) 0.0152(7) Uani 1 1 d . . . . . H23 H 1.1329 0.4553 0.5918 0.018 Uiso 1 1 calc R . . . . C24 C 1.1196(4) 0.6358(3) 0.62906(13) 0.0199(8) Uani 1 1 d . . . . . H24A H 1.0504 0.7144 0.6274 0.030 Uiso 1 1 calc GR . . . . H24B H 1.2312 0.6597 0.6196 0.030 Uiso 1 1 calc GR . . . . H24C H 1.1180 0.5999 0.6645 0.030 Uiso 1 1 calc GR . . . . O25 O 0.8662(3) 0.2791(2) 0.50875(8) 0.0190(6) Uani 1 1 d . . . . . H25 H 0.8931 0.2558 0.4786 0.029 Uiso 1 1 calc GR . . . . C26 C 1.0479(4) 0.5833(3) 0.53551(12) 0.0140(7) Uani 1 1 d . . . . . C27 C 1.1274(4) 0.5163(3) 0.49609(13) 0.0201(8) Uani 1 1 d . . . . . H27 H 1.1826 0.4361 0.5036 0.024 Uiso 1 1 calc R . . . . C28 C 1.1271(5) 0.5654(4) 0.44563(14) 0.0225(9) Uani 1 1 d . . . . . H28 H 1.1822 0.5189 0.4188 0.027 Uiso 1 1 calc R . . . . C29 C 1.0466(4) 0.6822(3) 0.43450(13) 0.0216(8) Uani 1 1 d . . . . . H29 H 1.0469 0.7160 0.4000 0.026 Uiso 1 1 calc R . . . . C30 C 0.9655(4) 0.7497(3) 0.47360(12) 0.0205(7) Uani 1 1 d . . . . . H30 H 0.9100 0.8296 0.4660 0.025 Uiso 1 1 calc R . . . . C31 C 0.9658(4) 0.6999(3) 0.52410(13) 0.0181(8) Uani 1 1 d . . . . . H31 H 0.9096 0.7458 0.5509 0.022 Uiso 1 1 calc R . . . . O32 O 0.3910(3) 0.3015(2) 0.59040(8) 0.0231(6) 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 0.0111(17) 0.0116(16) 0.0161(16) -0.0026(14) 0.0017(13) -0.0036(14) C2 0.0112(18) 0.0157(17) 0.0174(18) 0.0004(14) -0.0010(14) -0.0056(14) C3 0.0168(19) 0.0205(19) 0.0203(18) -0.0085(15) 0.0016(17) -0.0023(17) C4 0.0161(19) 0.0175(18) 0.028(2) -0.0066(16) 0.0019(17) 0.0014(15) C5 0.0151(19) 0.0150(17) 0.025(2) 0.0003(16) 0.0009(17) -0.0029(14) C6 0.018(2) 0.0158(19) 0.040(2) 0.0015(18) -0.0044(18) -0.0021(17) C7 0.024(2) 0.020(2) 0.031(2) 0.0111(17) -0.0109(19) -0.0048(17) C8 0.023(2) 0.028(2) 0.0207(19) 0.0056(17) 0.0004(17) -0.0108(17) C9 0.0132(19) 0.0181(17) 0.0210(18) 0.0026(15) 0.0021(15) -0.0029(14) C10 0.0146(19) 0.0116(16) 0.0192(18) -0.0002(13) -0.0002(15) -0.0052(14) N11 0.0163(15) 0.0146(15) 0.0158(15) -0.0003(12) 0.0044(13) 0.0019(12) C12 0.0195(19) 0.0140(17) 0.0071(16) -0.0005(13) -0.0003(15) 0.0004(14) C13 0.0161(19) 0.0170(17) 0.0124(17) 0.0009(15) 0.0036(16) -0.0004(14) N14 0.0175(16) 0.0181(15) 0.0197(16) 0.0001(13) 0.0039(14) 0.0001(12) N15 0.0197(16) 0.0153(14) 0.0237(16) 0.0001(14) 0.0065(15) 0.0043(12) S16 0.0169(4) 0.0185(4) 0.0162(4) -0.0049(4) 0.0035(4) -0.0030(4) C17 0.0147(18) 0.0149(17) 0.0152(17) -0.0027(14) 0.0024(15) -0.0040(14) C18 0.0171(19) 0.0206(19) 0.0162(18) 0.0032(15) -0.0009(16) -0.0029(15) C19 0.0164(19) 0.022(2) 0.021(2) -0.0038(16) 0.0024(16) -0.0012(16) C20 0.024(2) 0.034(2) 0.0118(18) -0.0038(16) 0.0030(16) -0.0089(18) C21 0.027(2) 0.030(2) 0.0179(17) 0.0086(17) -0.0055(16) -0.003(2) C22 0.0155(18) 0.0201(19) 0.0251(19) 0.0049(15) -0.0010(16) 0.0011(15) C23 0.0118(18) 0.0160(17) 0.0177(17) 0.0001(14) 0.0032(15) 0.0005(14) C24 0.022(2) 0.0198(18) 0.0182(19) -0.0011(16) -0.0001(17) -0.0035(15) O25 0.0220(14) 0.0235(14) 0.0117(12) -0.0030(10) -0.0002(10) 0.0033(11) C26 0.0115(18) 0.0154(17) 0.0150(17) -0.0008(14) 0.0020(15) -0.0052(15) C27 0.020(2) 0.0166(18) 0.023(2) -0.0014(16) 0.0066(17) 0.0004(16) C28 0.024(2) 0.024(2) 0.019(2) -0.0064(16) 0.0067(17) -0.0055(17) C29 0.024(2) 0.027(2) 0.0143(17) 0.0009(15) 0.0003(16) -0.0084(17) C30 0.0212(18) 0.0198(17) 0.0205(17) 0.0035(16) -0.0024(16) -0.0025(19) C31 0.0167(18) 0.0197(17) 0.0179(17) -0.0009(15) 0.0016(15) 0.0004(16) O32 0.0196(14) 0.0377(15) 0.0120(12) -0.0049(11) -0.0007(10) -0.0034(11) 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 C10 120.4(3) . . ? C2 C1 C12 118.5(3) . . ? C10 C1 C12 121.1(3) . . ? C1 C2 C3 120.4(3) . . ? O25 C2 C1 117.0(3) . . ? O25 C2 C3 122.6(3) . . ? C2 C3 H3 119.9 . . ? C4 C3 C2 120.2(3) . . ? C4 C3 H3 119.9 . . ? C3 C4 H4 119.2 . . ? C3 C4 C5 121.5(3) . . ? C5 C4 H4 119.2 . . ? C4 C5 C10 118.7(3) . . ? C6 C5 C4 122.1(3) . . ? C6 C5 C10 119.2(3) . . ? C5 C6 H6 119.4 . . ? C7 C6 C5 121.2(4) . . ? C7 C6 H6 119.4 . . ? C6 C7 H7 120.0 . . ? C6 C7 C8 119.9(3) . . ? C8 C7 H7 120.0 . . ? C7 C8 H8 119.6 . . ? C9 C8 C7 120.7(3) . . ? C9 C8 H8 119.6 . . ? C8 C9 H9 119.6 . . ? C8 C9 C10 120.9(3) . . ? C10 C9 H9 119.6 . . ? C1 C10 C5 118.8(3) . . ? C9 C10 C1 123.1(3) . . ? C9 C10 C5 118.1(3) . . ? C12 N11 C23 128.8(3) . . ? N15 N11 C12 111.7(3) . . ? N15 N11 C23 119.2(3) . . ? N11 C12 C1 124.4(3) . . ? N11 C12 C13 102.8(3) . . ? C13 C12 C1 132.8(3) . . ? C12 C13 S16 127.0(2) . . ? N14 C13 C12 110.4(3) . . ? N14 C13 S16 122.4(3) . . ? N15 N14 C13 107.7(3) . . ? N14 N15 N11 107.4(2) . . ? C13 S16 C17 97.66(15) . . ? O32 S16 C13 105.69(15) . . ? O32 S16 C17 106.68(15) . . ? C18 C17 S16 119.7(3) . . ? C22 C17 S16 118.6(3) . . ? C22 C17 C18 121.7(3) . . ? C17 C18 H18 120.6 . . ? C17 C18 C19 118.7(3) . . ? C19 C18 H18 120.6 . . ? C18 C19 H19 119.9 . . ? C20 C19 C18 120.2(3) . . ? C20 C19 H19 119.9 . . ? C19 C20 H20 119.8 . . ? C19 C20 C21 120.4(3) . . ? C21 C20 H20 119.8 . . ? C20 C21 H21 120.0 . . ? C22 C21 C20 120.1(3) . . ? C22 C21 H21 120.0 . . ? C17 C22 C21 119.0(3) . . ? C17 C22 H22 120.5 . . ? C21 C22 H22 120.5 . . ? N11 C23 H23 108.0 . . ? N11 C23 C24 109.9(3) . . ? N11 C23 C26 110.5(3) . . ? C24 C23 H23 108.0 . . ? C26 C23 H23 108.0 . . ? C26 C23 C24 112.3(3) . . ? 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 . . ? C2 O25 H25 109.5 . . ? C27 C26 C23 119.9(3) . . ? C27 C26 C31 119.4(3) . . ? C31 C26 C23 120.6(3) . . ? C26 C27 H27 119.8 . . ? C26 C27 C28 120.5(3) . . ? C28 C27 H27 119.8 . . ? C27 C28 H28 120.0 . . ? C29 C28 C27 119.9(3) . . ? C29 C28 H28 120.0 . . ? C28 C29 H29 120.0 . . ? C28 C29 C30 120.1(3) . . ? C30 C29 H29 120.0 . . ? C29 C30 H30 120.1 . . ? C29 C30 C31 119.8(3) . . ? C31 C30 H30 120.1 . . ? C26 C31 C30 120.3(3) . . ? 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 1.380(4) . ? C1 C10 1.424(4) . ? C1 C12 1.479(4) . ? C2 C3 1.415(5) . ? C2 O25 1.355(4) . ? C3 H3 0.9500 . ? C3 C4 1.358(5) . ? C4 H4 0.9500 . ? C4 C5 1.418(5) . ? C5 C6 1.416(5) . ? C5 C10 1.430(4) . ? C6 H6 0.9500 . ? C6 C7 1.364(5) . ? C7 H7 0.9500 . ? C7 C8 1.409(5) . ? C8 H8 0.9500 . ? C8 C9 1.373(5) . ? C9 H9 0.9500 . ? C9 C10 1.420(4) . ? N11 C12 1.361(4) . ? N11 N15 1.355(4) . ? N11 C23 1.480(4) . ? C12 C13 1.375(5) . ? C13 N14 1.369(4) . ? C13 S16 1.760(3) . ? N14 N15 1.318(4) . ? S16 C17 1.791(3) . ? S16 O32 1.505(2) . ? C17 C18 1.382(4) . ? C17 C22 1.379(4) . ? C18 H18 0.9500 . ? C18 C19 1.391(5) . ? C19 H19 0.9500 . ? C19 C20 1.376(5) . ? C20 H20 0.9500 . ? C20 C21 1.386(5) . ? C21 H21 0.9500 . ? C21 C22 1.383(4) . ? C22 H22 0.9500 . ? C23 H23 1.0000 . ? C23 C24 1.524(4) . ? C23 C26 1.524(4) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? O25 H25 0.8400 . ? C26 C27 1.383(4) . ? C26 C31 1.392(5) . ? C27 H27 0.9500 . ? C27 C28 1.389(5) . ? C28 H28 0.9500 . ? C28 C29 1.385(5) . ? C29 H29 0.9500 . ? C29 C30 1.386(5) . ? C30 H30 0.9500 . ? C30 C31 1.392(4) . ? 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 -1.2(5) . . . . ? C1 C12 C13 N14 179.6(3) . . . . ? C1 C12 C13 S16 -5.4(6) . . . . ? C2 C1 C10 C5 1.8(5) . . . . ? C2 C1 C10 C9 -178.7(3) . . . . ? C2 C1 C12 N11 -84.9(4) . . . . ? C2 C1 C12 C13 95.2(4) . . . . ? C2 C3 C4 C5 2.0(5) . . . . ? C3 C4 C5 C6 -178.8(3) . . . . ? C3 C4 C5 C10 -0.9(5) . . . . ? C4 C5 C6 C7 -179.9(3) . . . . ? C4 C5 C10 C1 -1.0(4) . . . . ? C4 C5 C10 C9 179.4(3) . . . . ? C5 C6 C7 C8 -0.5(6) . . . . ? C6 C5 C10 C1 177.0(3) . . . . ? C6 C5 C10 C9 -2.5(5) . . . . ? C6 C7 C8 C9 -0.7(5) . . . . ? C7 C8 C9 C10 0.3(5) . . . . ? C8 C9 C10 C1 -178.2(3) . . . . ? C8 C9 C10 C5 1.4(5) . . . . ? C10 C1 C2 C3 -0.7(5) . . . . ? C10 C1 C2 O25 178.6(3) . . . . ? C10 C1 C12 N11 93.6(4) . . . . ? C10 C1 C12 C13 -86.2(5) . . . . ? C10 C5 C6 C7 2.2(5) . . . . ? N11 C12 C13 N14 -0.2(4) . . . . ? N11 C12 C13 S16 174.7(3) . . . . ? N11 C23 C26 C27 -112.4(3) . . . . ? N11 C23 C26 C31 70.0(4) . . . . ? C12 C1 C2 C3 177.9(3) . . . . ? C12 C1 C2 O25 -2.8(4) . . . . ? C12 C1 C10 C5 -176.7(3) . . . . ? C12 C1 C10 C9 2.8(5) . . . . ? C12 N11 N15 N14 0.2(4) . . . . ? C12 N11 C23 C24 -138.6(3) . . . . ? C12 N11 C23 C26 96.8(4) . . . . ? C12 C13 N14 N15 0.3(4) . . . . ? C12 C13 S16 C17 128.7(3) . . . . ? C12 C13 S16 O32 -121.5(3) . . . . ? C13 N14 N15 N11 -0.3(4) . . . . ? C13 S16 C17 C18 88.0(3) . . . . ? C13 S16 C17 C22 -93.5(3) . . . . ? N14 C13 S16 C17 -56.9(3) . . . . ? N14 C13 S16 O32 52.9(3) . . . . ? N15 N11 C12 C1 -179.8(3) . . . . ? N15 N11 C12 C13 0.0(3) . . . . ? N15 N11 C23 C24 47.9(4) . . . . ? N15 N11 C23 C26 -76.6(4) . . . . ? S16 C13 N14 N15 -174.9(2) . . . . ? S16 C17 C18 C19 178.6(3) . . . . ? S16 C17 C22 C21 -178.8(3) . . . . ? C17 C18 C19 C20 0.0(5) . . . . ? C18 C17 C22 C21 -0.3(5) . . . . ? C18 C19 C20 C21 0.2(5) . . . . ? C19 C20 C21 C22 -0.4(5) . . . . ? C20 C21 C22 C17 0.5(5) . . . . ? C22 C17 C18 C19 0.1(5) . . . . ? C23 N11 C12 C1 6.3(5) . . . . ? C23 N11 C12 C13 -173.8(3) . . . . ? C23 N11 N15 N14 174.7(3) . . . . ? C23 C26 C27 C28 -176.9(3) . . . . ? C23 C26 C31 C30 176.7(3) . . . . ? C24 C23 C26 C27 124.5(3) . . . . ? C24 C23 C26 C31 -53.1(4) . . . . ? O25 C2 C3 C4 179.5(3) . . . . ? C26 C27 C28 C29 -0.1(5) . . . . ? C27 C26 C31 C30 -0.9(5) . . . . ? C27 C28 C29 C30 -0.3(5) . . . . ? C28 C29 C30 C31 0.2(5) . . . . ? C29 C30 C31 C26 0.4(5) . . . . ? C31 C26 C27 C28 0.7(5) . . . . ? O32 S16 C17 C18 -21.0(3) . . . . ? O32 S16 C17 C22 157.5(3) . . . . ?