#------------------------------------------------------------------------------ #$Date: 2020-07-06 06:42:45 +0300 (Mon, 06 Jul 2020) $ #$Revision: 253968 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/75/7157519.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_7157519 loop_ _publ_author_name 'Li, Ying-Xian' 'Cheng, Cheng' 'Tang, Lei' 'Yang, Yuan-Yong' _publ_section_title ; Palladium catalyzed asymmetric allylic alkylation of isoquinolinedione derivatives in the preparation of quaternary carbon stereocenters. ; _journal_issue 24 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 4551 _journal_page_last 4555 _journal_paper_doi 10.1039/d0ob00765j _journal_volume 18 _journal_year 2020 _chemical_absolute_configuration ad _chemical_formula_moiety 'C32 H29 N O S' _chemical_formula_sum 'C32 H29 N O S' _chemical_formula_weight 475.62 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2019-12-09 _audit_creation_method ; Olex2 1.3-alpha (compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003) ; _audit_update_record ; 2020-01-14 deposited with the CCDC. 2020-05-26 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 106.464(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.25182(19) _cell_length_b 14.2225(3) _cell_length_c 10.38203(19) _cell_measurement_reflns_used 3749 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 73.3640 _cell_measurement_theta_min 5.4150 _cell_volume 1310.10(5) _computing_cell_refinement 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 1.3-alpha (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3-alpha (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2684 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.971 _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 -57.00 -2.00 1.00 1.00 -- -40.98 125.00-120.00 55 2 \w 18.00 113.00 1.00 1.00 -- 40.98 38.00-180.00 95 3 \w 131.00 175.00 1.00 1.00 -- 106.95 125.00-120.00 44 4 \w 102.00 140.00 1.00 1.00 -- 106.95 125.00 -30.00 38 5 \w 74.00 135.00 1.00 1.00 -- 106.95 -30.00 0.00 61 6 \w 106.00 132.00 1.00 1.00 -- 106.95 -61.00 90.00 26 7 \w 34.00 127.00 1.00 1.00 -- 106.95 -30.00-120.00 93 8 \w 48.00 119.00 1.00 1.00 -- 106.95-125.00-150.00 71 9 \w 27.00 85.00 1.00 1.00 -- 106.95 -15.00-180.00 58 10 \w -95.00 -4.00 1.00 1.00 -- -40.98 125.00 150.00 91 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0588680000 _diffrn_orient_matrix_UB_12 0.0002194000 _diffrn_orient_matrix_UB_13 0.1248547000 _diffrn_orient_matrix_UB_21 -0.1427104000 _diffrn_orient_matrix_UB_22 -0.0530276000 _diffrn_orient_matrix_UB_23 -0.0797227000 _diffrn_orient_matrix_UB_31 0.0798877000 _diffrn_orient_matrix_UB_32 -0.0942947000 _diffrn_orient_matrix_UB_33 0.0446051000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0187 _diffrn_reflns_av_unetI/netI 0.0259 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.971 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 4890 _diffrn_reflns_point_group_measured_fraction_full 0.709 _diffrn_reflns_point_group_measured_fraction_max 0.678 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.527 _diffrn_reflns_theta_min 4.441 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.274 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.80494 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43f (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 1.206 _exptl_crystal_description block _exptl_crystal_F_000 504 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.157 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.035 _refine_ls_abs_structure_details ; Flack x determined using 844 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.052(17) _refine_ls_extinction_coef 0.0149(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 326 _refine_ls_number_reflns 3578 _refine_ls_number_restraints 8 _refine_ls_restrained_S_all 1.065 _refine_ls_R_factor_all 0.0369 _refine_ls_R_factor_gt 0.0360 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0680P)^2^+0.0028P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1005 _refine_ls_wR_factor_ref 0.1027 _reflns_Friedel_coverage 0.340 _reflns_Friedel_fraction_full 0.393 _reflns_Friedel_fraction_max 0.359 _reflns_number_gt 3452 _reflns_number_total 3578 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00765j2.cif _cod_data_source_block lyx620 _cod_depositor_comments 'Adding full bibliography for 7157519.cif.' _cod_original_cell_volume 1310.09(4) _cod_database_code 7157519 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.905 _shelx_estimated_absorpt_t_min 0.862 _reflns_odcompleteness_completeness 99.92 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Rigid bond restraints C3, C4 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01 3. Uiso/Uaniso restraints and constraints C3 \\sim C4: within 2A with sigma of 0.002 and sigma for terminal atoms of 0.004 within 2A 4.a Ternary CH refined with riding coordinates: C15(H15) 4.b Secondary CH2 refined with riding coordinates: C23(H23A,H23B), C7(H7A,H7B) 4.c Aromatic/amide H refined with riding coordinates: C22(H22), C21(H21), C30(H30), C18(H18), C24(H24), C20(H20), C13(H13), C9(H9), C2(H2), C19(H19), C29(H29), C6(H6), C27(H27), C12(H12), C28(H28), C3(H3), C10(H10), C5(H5), C4(H4) 4.d Idealised Me refined as rotating group: C14(H14A,H14B,H14C) ; _shelx_res_file ; TITL lyx620_a.res in P2(1) lyx620.res created by SHELXL-2018/3 at 17:54:30 on 09-Dec-2019 REM Old TITL lyx620 in P2(1) REM SHELXT solution in P2(1): R1 0.140, Rweak 0.043, Alpha 0.002 REM 0.429 for 4 systematic absences, Orientation as input REM Flack x = 0.197 ( 0.017 ) from 450 Parsons' quotients REM Formula found by SHELXT: C30 N2 O2 Cl CELL 1.54184 9.25182 14.222483 10.382034 90 106.4641 90 ZERR 2 0.000186 0.00025 0.000193 0 0.002 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H N O S UNIT 64 58 2 2 2 SIMU 0.002 0.004 2 C3 C4 DELU C3 C4 L.S. 10 PLAN 5 SIZE 0.08 0.1 0.12 CONF BOND list 4 MORE -1 BOND $H fmap 2 acta REM REM REM WGHT 0.068000 0.002800 EXTI 0.014930 FVAR 11.47985 S1 5 0.495411 0.517405 0.559188 11.00000 0.06758 0.08826 = 0.05908 -0.00122 -0.00046 0.02659 O1 4 0.813965 0.503504 0.983185 11.00000 0.09408 0.09003 = 0.03532 -0.00729 0.01911 -0.01983 N1 3 0.664889 0.437052 0.794060 11.00000 0.05587 0.05455 = 0.03971 -0.00043 0.01715 -0.00128 C1 1 0.525142 0.303593 0.854509 11.00000 0.05662 0.07422 = 0.04623 -0.00169 0.02422 -0.00933 C22 1 0.967862 0.305480 0.769875 11.00000 0.04755 0.04879 = 0.05084 0.00188 0.00819 -0.00383 AFIX 43 H22 2 1.022749 0.359600 0.801833 11.00000 -1.20000 AFIX 0 C17 1 0.834769 0.312378 0.665590 11.00000 0.04909 0.04364 = 0.03498 -0.00105 0.01342 -0.00384 C16 1 0.770085 0.407314 0.603150 11.00000 0.05076 0.04429 = 0.03123 0.00013 0.00737 -0.00076 C23 1 0.720715 0.400854 0.447484 11.00000 0.06906 0.05447 = 0.03195 0.00035 0.00849 0.00054 AFIX 23 H23A 2 0.627523 0.365298 0.420211 11.00000 -1.20000 H23B 2 0.698562 0.463955 0.411913 11.00000 -1.20000 AFIX 0 C32 1 0.785916 0.488045 0.862133 11.00000 0.06661 0.05005 = 0.03798 0.00166 0.01369 0.00014 C8 1 0.570095 0.624476 0.638849 11.00000 0.07384 0.06944 = 0.05488 0.01477 0.01970 0.02783 C15 1 0.626707 0.424545 0.649619 11.00000 0.05128 0.05279 = 0.03862 -0.00060 0.00940 0.00158 AFIX 13 H15 2 0.569324 0.365742 0.631097 11.00000 -1.20000 AFIX 0 C31 1 0.887257 0.523712 0.783747 11.00000 0.06218 0.04427 = 0.03419 0.00277 0.01031 -0.00351 C21 1 1.019884 0.219102 0.826867 11.00000 0.05549 0.06146 = 0.05636 0.00983 0.00806 0.00528 AFIX 43 H21 2 1.107738 0.216441 0.897779 11.00000 -1.20000 AFIX 0 C26 1 0.879385 0.486738 0.656237 11.00000 0.05767 0.04240 = 0.03842 0.00338 0.01271 -0.00188 C30 1 0.989556 0.593892 0.838790 11.00000 0.08580 0.05463 = 0.04627 -0.00283 0.01229 -0.01496 AFIX 43 H30 2 0.993448 0.617911 0.923023 11.00000 -1.20000 AFIX 0 C18 1 0.758046 0.229216 0.620457 11.00000 0.06627 0.04964 = 0.04284 -0.00109 0.00459 -0.00874 AFIX 43 H18 2 0.668442 0.231440 0.551447 11.00000 -1.20000 AFIX 0 C24 1 0.829934 0.357166 0.382763 11.00000 0.09033 0.05656 = 0.04258 -0.00042 0.02243 0.00511 AFIX 43 H24 2 0.887100 0.306525 0.425919 11.00000 -1.20000 AFIX 0 C20 1 0.943593 0.137721 0.780095 11.00000 0.08205 0.04542 = 0.05751 0.00928 0.02220 0.00955 AFIX 43 H20 2 0.979546 0.079920 0.817640 11.00000 -1.20000 AFIX 0 C13 1 0.537414 0.652954 0.755516 11.00000 0.08793 0.06808 = 0.07041 0.01141 0.03749 0.02087 AFIX 43 H13 2 0.477591 0.615236 0.792758 11.00000 -1.20000 AFIX 0 C7 1 0.551514 0.408458 0.859905 11.00000 0.06882 0.07228 = 0.06242 -0.00215 0.03539 -0.00217 AFIX 23 H7A 2 0.457282 0.440074 0.816917 11.00000 -1.20000 H7B 2 0.583760 0.428365 0.953056 11.00000 -1.20000 AFIX 0 C9 1 0.654644 0.683735 0.584213 11.00000 0.10195 0.08468 = 0.06588 0.02304 0.03977 0.03389 AFIX 43 H9 2 0.676542 0.666620 0.505338 11.00000 -1.20000 AFIX 0 C2 1 0.386911 0.265542 0.786133 11.00000 0.05911 0.09546 = 0.06762 -0.00632 0.02195 -0.00556 AFIX 43 H2 2 0.308612 0.304954 0.741225 11.00000 -1.20000 AFIX 0 C19 1 0.811988 0.143431 0.675857 11.00000 0.08837 0.04472 = 0.05416 -0.00146 0.01424 -0.01325 AFIX 43 H19 2 0.759211 0.088822 0.642696 11.00000 -1.20000 AFIX 0 C29 1 1.085855 0.628732 0.770476 11.00000 0.09786 0.06358 = 0.06365 -0.00752 0.02102 -0.03621 AFIX 43 H29 2 1.154476 0.675881 0.808136 11.00000 -1.20000 AFIX 0 C6 1 0.639212 0.242309 0.917749 11.00000 0.06412 0.07735 = 0.06020 0.00631 0.01146 -0.01045 AFIX 43 H6 2 0.733630 0.266091 0.962858 11.00000 -1.20000 AFIX 0 C27 1 0.978378 0.522699 0.589327 11.00000 0.08032 0.05928 = 0.04970 -0.00145 0.02665 -0.01537 AFIX 43 H27 2 0.976231 0.498921 0.505359 11.00000 -1.20000 AFIX 0 C12 1 0.592909 0.736529 0.816310 11.00000 0.11018 0.06905 = 0.07871 0.00255 0.04177 0.02270 AFIX 43 H12 2 0.572351 0.753423 0.895853 11.00000 -1.20000 AFIX 0 C25 1 0.850105 0.386128 0.268110 11.00000 0.12341 0.08328 = 0.05290 0.00115 0.04271 0.00102 C28 1 1.079071 0.592657 0.645249 11.00000 0.09800 0.07064 = 0.06930 -0.00152 0.03766 -0.03238 AFIX 43 H28 2 1.143345 0.615986 0.598349 11.00000 -1.20000 AFIX 0 C11 1 0.678184 0.795877 0.762404 11.00000 0.10226 0.06137 = 0.09951 0.01648 0.03733 0.02702 C3 1 0.364347 0.168843 0.784139 11.00000 0.07892 0.09277 = 0.08652 -0.01844 0.03511 -0.02935 AFIX 43 H3 2 0.270706 0.144266 0.738430 11.00000 -1.20000 AFIX 0 C10 1 0.707085 0.767827 0.644710 11.00000 0.10726 0.07580 = 0.10096 0.03135 0.04757 0.02528 AFIX 43 H10 2 0.763398 0.806811 0.605491 11.00000 -1.20000 AFIX 0 C5 1 0.615372 0.146522 0.915078 11.00000 0.09262 0.07587 = 0.07642 0.01221 0.02669 -0.00387 AFIX 43 H5 2 0.693521 0.106688 0.959022 11.00000 -1.20000 AFIX 0 C4 1 0.478066 0.109419 0.848519 11.00000 0.08818 0.08531 = 0.08450 -0.00862 0.03967 -0.02435 AFIX 43 H4 2 0.462338 0.044797 0.847093 11.00000 -1.20000 AFIX 0 C14 1 0.740143 0.887654 0.832443 11.00000 0.17394 0.06709 = 0.17072 -0.00614 0.06335 0.01126 AFIX 137 H14A 2 0.687178 0.903306 0.896794 11.00000 -1.50000 H14B 2 0.726747 0.937033 0.767065 11.00000 -1.50000 H14C 2 0.845514 0.880406 0.877566 11.00000 -1.50000 AFIX 0 H25A 2 0.921152 0.354043 0.229067 11.00000 0.08311 H25B 2 0.793000 0.445989 0.221573 11.00000 0.10840 HKLF 4 REM lyx620_a.res in P2(1) REM wR2 = 0.1027, GooF = S = 1.056, Restrained GooF = 1.065 for all data REM R1 = 0.0360 for 3452 Fo > 4sig(Fo) and 0.0369 for all 3578 data REM 326 parameters refined using 8 restraints END WGHT 0.0688 0.0055 REM Highest difference peak 0.157, deepest hole -0.188, 1-sigma level 0.035 Q1 1 0.3406 0.3164 0.7554 11.00000 0.05 0.16 Q2 1 0.6984 0.4223 0.6171 11.00000 0.05 0.16 Q3 1 0.3145 0.2220 0.7407 11.00000 0.05 0.15 Q4 1 0.8004 0.3633 0.6375 11.00000 0.05 0.15 Q5 1 0.6119 0.4687 0.6014 11.00000 0.05 0.15 ; _shelx_res_checksum 70281 _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 1.271 _oxdiff_exptl_absorpt_empirical_full_min 0.817 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.49541(8) 0.51741(6) 0.55919(7) 0.0754(3) Uani 1 1 d . . . . . O1 O 0.8140(2) 0.50350(17) 0.98319(16) 0.0730(6) Uani 1 1 d . . . . . N1 N 0.6649(2) 0.43705(15) 0.79406(18) 0.0493(4) Uani 1 1 d . . . . . C1 C 0.5251(3) 0.3036(2) 0.8545(2) 0.0570(6) Uani 1 1 d . . . . . C22 C 0.9679(2) 0.30548(18) 0.7699(2) 0.0502(5) Uani 1 1 d . . . . . H22 H 1.022749 0.359600 0.801833 0.060 Uiso 1 1 calc R U . . . C17 C 0.8348(2) 0.31238(15) 0.66559(19) 0.0423(4) Uani 1 1 d . . . . . C16 C 0.7701(2) 0.40731(16) 0.60315(19) 0.0430(4) Uani 1 1 d . . . . . C23 C 0.7207(3) 0.40085(19) 0.4475(2) 0.0530(5) Uani 1 1 d . . . . . H23A H 0.627523 0.365298 0.420211 0.064 Uiso 1 1 calc R U . . . H23B H 0.698562 0.463955 0.411913 0.064 Uiso 1 1 calc R U . . . C32 C 0.7859(3) 0.48804(18) 0.8621(2) 0.0518(5) Uani 1 1 d . . . . . C8 C 0.5701(3) 0.6245(2) 0.6388(3) 0.0658(7) Uani 1 1 d . . . . . C15 C 0.6267(3) 0.42455(17) 0.6496(2) 0.0482(5) Uani 1 1 d . . . . . H15 H 0.569324 0.365742 0.631097 0.058 Uiso 1 1 calc R U . . . C31 C 0.8873(3) 0.52371(17) 0.78375(19) 0.0476(5) Uani 1 1 d . . . . . C21 C 1.0199(3) 0.21910(19) 0.8269(3) 0.0594(6) Uani 1 1 d . . . . . H21 H 1.107738 0.216441 0.897779 0.071 Uiso 1 1 calc R U . . . C26 C 0.8794(3) 0.48674(16) 0.6562(2) 0.0463(5) Uani 1 1 d . . . . . C30 C 0.9896(4) 0.5939(2) 0.8388(3) 0.0636(7) Uani 1 1 d . . . . . H30 H 0.993448 0.617911 0.923023 0.076 Uiso 1 1 calc R U . . . C18 C 0.7580(3) 0.22922(18) 0.6205(2) 0.0551(6) Uani 1 1 d . . . . . H18 H 0.668442 0.231440 0.551447 0.066 Uiso 1 1 calc R U . . . C24 C 0.8299(4) 0.3572(2) 0.3828(2) 0.0624(6) Uani 1 1 d . . . . . H24 H 0.887100 0.306525 0.425919 0.075 Uiso 1 1 calc R U . . . C20 C 0.9436(3) 0.13772(19) 0.7801(3) 0.0612(6) Uani 1 1 d . . . . . H20 H 0.979546 0.079920 0.817640 0.073 Uiso 1 1 calc R U . . . C13 C 0.5374(4) 0.6530(2) 0.7555(3) 0.0724(8) Uani 1 1 d . . . . . H13 H 0.477591 0.615236 0.792758 0.087 Uiso 1 1 calc R U . . . C7 C 0.5515(3) 0.4085(2) 0.8599(3) 0.0644(7) Uani 1 1 d . . . . . H7A H 0.457282 0.440074 0.816917 0.077 Uiso 1 1 calc R U . . . H7B H 0.583760 0.428365 0.953056 0.077 Uiso 1 1 calc R U . . . C9 C 0.6546(4) 0.6837(3) 0.5842(3) 0.0809(10) Uani 1 1 d . . . . . H9 H 0.676542 0.666620 0.505338 0.097 Uiso 1 1 calc R U . . . C2 C 0.3869(3) 0.2655(3) 0.7861(3) 0.0732(8) Uani 1 1 d . . . . . H2 H 0.308612 0.304954 0.741225 0.088 Uiso 1 1 calc R U . . . C19 C 0.8120(4) 0.14343(18) 0.6759(3) 0.0636(7) Uani 1 1 d . . . . . H19 H 0.759211 0.088822 0.642696 0.076 Uiso 1 1 calc R U . . . C29 C 1.0859(4) 0.6287(2) 0.7705(3) 0.0754(8) Uani 1 1 d . . . . . H29 H 1.154476 0.675881 0.808136 0.090 Uiso 1 1 calc R U . . . C6 C 0.6392(3) 0.2423(2) 0.9177(3) 0.0685(7) Uani 1 1 d . . . . . H6 H 0.733630 0.266091 0.962858 0.082 Uiso 1 1 calc R U . . . C27 C 0.9784(3) 0.5227(2) 0.5893(2) 0.0614(6) Uani 1 1 d . . . . . H27 H 0.976231 0.498921 0.505359 0.074 Uiso 1 1 calc R U . . . C12 C 0.5929(4) 0.7365(2) 0.8163(4) 0.0829(9) Uani 1 1 d . . . . . H12 H 0.572351 0.753423 0.895853 0.099 Uiso 1 1 calc R U . . . C25 C 0.8501(5) 0.3861(3) 0.2681(3) 0.0829(10) Uani 1 1 d . . . . . C28 C 1.0791(4) 0.5927(2) 0.6452(3) 0.0764(9) Uani 1 1 d . . . . . H28 H 1.143345 0.615986 0.598349 0.092 Uiso 1 1 calc R U . . . C11 C 0.6782(5) 0.7959(3) 0.7624(4) 0.0859(10) Uani 1 1 d . . . . . C3 C 0.3643(4) 0.1688(3) 0.7841(4) 0.0837(8) Uani 1 1 d . U . . . H3 H 0.270706 0.144266 0.738430 0.100 Uiso 1 1 calc R U . . . C10 C 0.7071(5) 0.7678(3) 0.6447(4) 0.0910(11) Uani 1 1 d . . . . . H10 H 0.763398 0.806811 0.605491 0.109 Uiso 1 1 calc R U . . . C5 C 0.6154(5) 0.1465(3) 0.9151(3) 0.0811(9) Uani 1 1 d . . . . . H5 H 0.693521 0.106688 0.959022 0.097 Uiso 1 1 calc R U . . . C4 C 0.4781(4) 0.1094(3) 0.8485(4) 0.0829(8) Uani 1 1 d . U . . . H4 H 0.462338 0.044797 0.847093 0.099 Uiso 1 1 calc R U . . . C14 C 0.7401(8) 0.8877(3) 0.8324(7) 0.1343(19) Uani 1 1 d . . . . . H14A H 0.687178 0.903306 0.896794 0.201 Uiso 1 1 calc R U . . . H14B H 0.726747 0.937033 0.767065 0.201 Uiso 1 1 calc R U . . . H14C H 0.845514 0.880406 0.877566 0.201 Uiso 1 1 calc R U . . . H25A H 0.921(4) 0.354(3) 0.229(4) 0.083(10) Uiso 1 1 d . . . . . H25B H 0.793(5) 0.446(3) 0.222(4) 0.108(14) Uiso 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 S1 0.0676(4) 0.0883(5) 0.0591(3) -0.0012(4) -0.0005(3) 0.0266(4) O1 0.0941(12) 0.0900(15) 0.0353(7) -0.0073(9) 0.0191(7) -0.0198(12) N1 0.0559(10) 0.0545(11) 0.0397(8) -0.0004(8) 0.0172(8) -0.0013(9) C1 0.0566(12) 0.0742(16) 0.0462(11) -0.0017(12) 0.0242(9) -0.0093(12) C22 0.0475(11) 0.0488(12) 0.0508(11) 0.0019(10) 0.0082(9) -0.0038(10) C17 0.0491(10) 0.0436(11) 0.0350(8) -0.0010(8) 0.0134(7) -0.0038(9) C16 0.0508(10) 0.0443(11) 0.0312(8) 0.0001(8) 0.0074(7) -0.0008(9) C23 0.0691(13) 0.0545(13) 0.0320(9) 0.0003(9) 0.0085(9) 0.0005(11) C32 0.0666(13) 0.0501(12) 0.0380(9) 0.0017(9) 0.0137(9) 0.0001(11) C8 0.0738(16) 0.0694(17) 0.0549(13) 0.0148(13) 0.0197(12) 0.0278(15) C15 0.0513(11) 0.0528(13) 0.0386(10) -0.0006(9) 0.0094(8) 0.0016(10) C31 0.0622(11) 0.0443(11) 0.0342(8) 0.0028(9) 0.0103(8) -0.0035(10) C21 0.0555(12) 0.0615(15) 0.0564(12) 0.0098(12) 0.0081(10) 0.0053(12) C26 0.0577(11) 0.0424(10) 0.0384(9) 0.0034(9) 0.0127(8) -0.0019(10) C30 0.0858(18) 0.0546(14) 0.0463(12) -0.0028(11) 0.0123(12) -0.0150(13) C18 0.0663(14) 0.0496(13) 0.0428(11) -0.0011(10) 0.0046(10) -0.0087(11) C24 0.0903(18) 0.0566(14) 0.0426(11) -0.0004(11) 0.0224(11) 0.0051(14) C20 0.0821(17) 0.0454(13) 0.0575(13) 0.0093(11) 0.0222(12) 0.0095(13) C13 0.088(2) 0.0681(18) 0.0704(16) 0.0114(14) 0.0375(15) 0.0209(16) C7 0.0688(15) 0.0723(17) 0.0624(14) -0.0022(13) 0.0354(12) -0.0022(14) C9 0.102(2) 0.085(2) 0.0659(16) 0.0230(17) 0.0398(16) 0.034(2) C2 0.0591(14) 0.095(2) 0.0676(15) -0.0063(16) 0.0220(12) -0.0056(15) C19 0.0884(18) 0.0447(13) 0.0542(13) -0.0015(11) 0.0142(12) -0.0133(13) C29 0.098(2) 0.0636(17) 0.0637(15) -0.0075(14) 0.0210(14) -0.0362(17) C6 0.0641(15) 0.0774(19) 0.0602(14) 0.0063(14) 0.0115(11) -0.0105(14) C27 0.0803(15) 0.0593(14) 0.0497(11) -0.0014(12) 0.0267(11) -0.0154(14) C12 0.110(3) 0.069(2) 0.0787(19) 0.0026(16) 0.0418(18) 0.0227(19) C25 0.123(3) 0.083(2) 0.0529(14) 0.0012(16) 0.0427(17) 0.001(2) C28 0.098(2) 0.0706(18) 0.0693(17) -0.0015(15) 0.0377(16) -0.0324(17) C11 0.102(2) 0.0614(18) 0.100(2) 0.0165(18) 0.0373(19) 0.0270(18) C3 0.0789(17) 0.093(2) 0.0865(18) -0.0184(16) 0.0351(14) -0.0293(15) C10 0.107(3) 0.076(2) 0.101(2) 0.031(2) 0.048(2) 0.025(2) C5 0.093(2) 0.076(2) 0.0764(19) 0.0122(17) 0.0267(16) -0.0039(18) C4 0.0882(17) 0.085(2) 0.0845(18) -0.0086(15) 0.0397(15) -0.0244(15) C14 0.174(5) 0.067(3) 0.171(5) -0.006(3) 0.063(4) 0.011(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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 C8 S1 C15 105.17(12) . . ? C32 N1 C15 121.91(19) . . ? C32 N1 C7 120.12(19) . . ? C15 N1 C7 116.9(2) . . ? C2 C1 C7 121.4(3) . . ? C2 C1 C6 117.8(3) . . ? C6 C1 C7 120.8(3) . . ? C17 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? C21 C22 C17 121.1(2) . . ? C22 C17 C16 122.7(2) . . ? C18 C17 C22 117.1(2) . . ? C18 C17 C16 120.16(18) . . ? C17 C16 C23 110.50(17) . . ? C17 C16 C15 105.73(16) . . ? C23 C16 C15 107.90(18) . . ? C26 C16 C17 111.15(17) . . ? C26 C16 C23 113.12(18) . . ? C26 C16 C15 108.09(18) . . ? C16 C23 H23A 108.0 . . ? C16 C23 H23B 108.0 . . ? H23A C23 H23B 107.3 . . ? C24 C23 C16 117.0(2) . . ? C24 C23 H23A 108.0 . . ? C24 C23 H23B 108.0 . . ? O1 C32 N1 122.3(2) . . ? O1 C32 C31 120.9(2) . . ? N1 C32 C31 116.86(18) . . ? C13 C8 S1 120.2(3) . . ? C9 C8 S1 121.6(2) . . ? C9 C8 C13 118.0(3) . . ? S1 C15 H15 105.5 . . ? N1 C15 S1 111.58(16) . . ? N1 C15 C16 111.16(18) . . ? N1 C15 H15 105.5 . . ? C16 C15 S1 116.64(15) . . ? C16 C15 H15 105.5 . . ? C26 C31 C32 120.8(2) . . ? C30 C31 C32 118.8(2) . . ? C30 C31 C26 120.4(2) . . ? C22 C21 H21 119.5 . . ? C20 C21 C22 121.0(2) . . ? C20 C21 H21 119.5 . . ? C31 C26 C16 118.23(19) . . ? C27 C26 C16 123.9(2) . . ? C27 C26 C31 117.7(2) . . ? C31 C30 H30 119.6 . . ? C29 C30 C31 120.9(2) . . ? C29 C30 H30 119.6 . . ? C17 C18 H18 119.3 . . ? C19 C18 C17 121.4(2) . . ? C19 C18 H18 119.3 . . ? C23 C24 H24 118.0 . . ? C25 C24 C23 124.1(3) . . ? C25 C24 H24 118.0 . . ? C21 C20 H20 120.7 . . ? C21 C20 C19 118.6(2) . . ? C19 C20 H20 120.7 . . ? C8 C13 H13 119.8 . . ? C12 C13 C8 120.5(3) . . ? C12 C13 H13 119.8 . . ? N1 C7 C1 112.8(2) . . ? N1 C7 H7A 109.0 . . ? N1 C7 H7B 109.0 . . ? C1 C7 H7A 109.0 . . ? C1 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C8 C9 H9 119.6 . . ? C10 C9 C8 120.9(3) . . ? C10 C9 H9 119.6 . . ? C1 C2 H2 119.8 . . ? C1 C2 C3 120.5(3) . . ? C3 C2 H2 119.8 . . ? C18 C19 C20 120.8(2) . . ? C18 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? C30 C29 H29 120.4 . . ? C30 C29 C28 119.1(3) . . ? C28 C29 H29 120.4 . . ? C1 C6 H6 119.4 . . ? C5 C6 C1 121.1(3) . . ? C5 C6 H6 119.4 . . ? C26 C27 H27 119.4 . . ? C28 C27 C26 121.2(2) . . ? C28 C27 H27 119.4 . . ? C13 C12 H12 119.2 . . ? C13 C12 C11 121.7(3) . . ? C11 C12 H12 119.2 . . ? C24 C25 H25A 121(2) . . ? C24 C25 H25B 119(2) . . ? H25A C25 H25B 120(3) . . ? C29 C28 H28 119.6 . . ? C27 C28 C29 120.7(3) . . ? C27 C28 H28 119.6 . . ? C12 C11 C10 117.3(4) . . ? C12 C11 C14 120.8(4) . . ? C10 C11 C14 121.9(4) . . ? C2 C3 H3 119.6 . . ? C4 C3 C2 120.8(3) . . ? C4 C3 H3 119.6 . . ? C9 C10 C11 121.6(4) . . ? C9 C10 H10 119.2 . . ? C11 C10 H10 119.2 . . ? C6 C5 H5 119.6 . . ? C4 C5 C6 120.8(4) . . ? C4 C5 H5 119.6 . . ? C3 C4 H4 120.5 . . ? C5 C4 C3 119.0(4) . . ? C5 C4 H4 120.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? 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 S1 C8 1.777(3) . ? S1 C15 1.859(2) . ? O1 C32 1.229(3) . ? N1 C32 1.353(3) . ? N1 C15 1.451(3) . ? N1 C7 1.463(3) . ? C1 C7 1.510(4) . ? C1 C2 1.385(4) . ? C1 C6 1.383(4) . ? C22 H22 0.9300 . ? C22 C17 1.394(3) . ? C22 C21 1.389(3) . ? C17 C16 1.543(3) . ? C17 C18 1.391(3) . ? C16 C23 1.553(3) . ? C16 C15 1.554(3) . ? C16 C26 1.512(3) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C23 C24 1.498(4) . ? C32 C31 1.494(3) . ? C8 C13 1.389(4) . ? C8 C9 1.377(5) . ? C15 H15 0.9800 . ? C31 C26 1.407(3) . ? C31 C30 1.383(4) . ? C21 H21 0.9300 . ? C21 C20 1.371(4) . ? C26 C27 1.394(3) . ? C30 H30 0.9300 . ? C30 C29 1.379(4) . ? C18 H18 0.9300 . ? C18 C19 1.380(4) . ? C24 H24 0.9300 . ? C24 C25 1.322(4) . ? C20 H20 0.9300 . ? C20 C19 1.383(4) . ? C13 H13 0.9300 . ? C13 C12 1.375(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C9 H9 0.9300 . ? C9 C10 1.374(6) . ? C2 H2 0.9300 . ? C2 C3 1.390(5) . ? C19 H19 0.9300 . ? C29 H29 0.9300 . ? C29 C28 1.382(4) . ? C6 H6 0.9300 . ? C6 C5 1.379(4) . ? C27 H27 0.9300 . ? C27 C28 1.374(4) . ? C12 H12 0.9300 . ? C12 C11 1.378(5) . ? C25 H25A 0.98(4) . ? C25 H25B 1.05(5) . ? C28 H28 0.9300 . ? C11 C10 1.382(5) . ? C11 C14 1.525(6) . ? C3 H3 0.9300 . ? C3 C4 1.367(6) . ? C10 H10 0.9300 . ? C5 H5 0.9300 . ? C5 C4 1.368(5) . ? C4 H4 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? 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 S1 C8 C13 C12 -178.9(3) . . . . ? S1 C8 C9 C10 177.7(3) . . . . ? O1 C32 C31 C26 163.2(2) . . . . ? O1 C32 C31 C30 -16.7(4) . . . . ? N1 C32 C31 C26 -15.6(3) . . . . ? N1 C32 C31 C30 164.5(2) . . . . ? C1 C2 C3 C4 -0.5(5) . . . . ? C1 C6 C5 C4 0.6(5) . . . . ? C22 C17 C16 C23 134.2(2) . . . . ? C22 C17 C16 C15 -109.3(2) . . . . ? C22 C17 C16 C26 7.8(3) . . . . ? C22 C17 C18 C19 -0.5(4) . . . . ? C22 C21 C20 C19 -0.9(4) . . . . ? C17 C22 C21 C20 1.5(4) . . . . ? C17 C16 C23 C24 -47.4(3) . . . . ? C17 C16 C15 S1 -165.36(14) . . . . ? C17 C16 C15 N1 65.2(2) . . . . ? C17 C16 C26 C31 -79.5(2) . . . . ? C17 C16 C26 C27 97.2(3) . . . . ? C17 C18 C19 C20 1.1(4) . . . . ? C16 C17 C18 C19 -179.0(2) . . . . ? C16 C23 C24 C25 -143.0(3) . . . . ? C16 C26 C27 C28 -177.5(3) . . . . ? C23 C16 C15 S1 -47.1(2) . . . . ? C23 C16 C15 N1 -176.6(2) . . . . ? C23 C16 C26 C31 155.5(2) . . . . ? C23 C16 C26 C27 -27.7(3) . . . . ? C32 N1 C15 S1 -91.0(2) . . . . ? C32 N1 C15 C16 41.0(3) . . . . ? C32 N1 C7 C1 -124.9(3) . . . . ? C32 C31 C26 C16 -2.4(3) . . . . ? C32 C31 C26 C27 -179.4(2) . . . . ? C32 C31 C30 C29 179.7(3) . . . . ? C8 S1 C15 N1 45.3(2) . . . . ? C8 S1 C15 C16 -83.93(18) . . . . ? C8 C13 C12 C11 2.0(5) . . . . ? C8 C9 C10 C11 0.4(6) . . . . ? C15 S1 C8 C13 -83.6(2) . . . . ? C15 S1 C8 C9 99.8(2) . . . . ? C15 N1 C32 O1 175.7(2) . . . . ? C15 N1 C32 C31 -5.5(3) . . . . ? C15 N1 C7 C1 66.8(3) . . . . ? C15 C16 C23 C24 -162.6(2) . . . . ? C15 C16 C26 C31 36.1(3) . . . . ? C15 C16 C26 C27 -147.2(2) . . . . ? C31 C26 C27 C28 -0.7(4) . . . . ? C31 C30 C29 C28 0.1(5) . . . . ? C21 C22 C17 C16 177.7(2) . . . . ? C21 C22 C17 C18 -0.8(3) . . . . ? C21 C20 C19 C18 -0.3(4) . . . . ? C26 C16 C23 C24 77.9(3) . . . . ? C26 C16 C15 S1 75.54(19) . . . . ? C26 C16 C15 N1 -53.9(2) . . . . ? C26 C31 C30 C29 -0.2(4) . . . . ? C26 C27 C28 C29 0.6(5) . . . . ? C30 C31 C26 C16 177.5(2) . . . . ? C30 C31 C26 C27 0.5(4) . . . . ? C30 C29 C28 C27 -0.3(6) . . . . ? C18 C17 C16 C23 -47.4(3) . . . . ? C18 C17 C16 C15 69.1(2) . . . . ? C18 C17 C16 C26 -173.8(2) . . . . ? C13 C8 C9 C10 1.0(5) . . . . ? C13 C12 C11 C10 -0.5(5) . . . . ? C13 C12 C11 C14 -179.3(4) . . . . ? C7 N1 C32 O1 7.9(4) . . . . ? C7 N1 C32 C31 -173.3(2) . . . . ? C7 N1 C15 S1 77.1(2) . . . . ? C7 N1 C15 C16 -150.8(2) . . . . ? C7 C1 C2 C3 -179.0(3) . . . . ? C7 C1 C6 C5 179.0(3) . . . . ? C9 C8 C13 C12 -2.2(4) . . . . ? C2 C1 C7 N1 -116.2(3) . . . . ? C2 C1 C6 C5 -1.2(4) . . . . ? C2 C3 C4 C5 -0.2(5) . . . . ? C6 C1 C7 N1 63.6(3) . . . . ? C6 C1 C2 C3 1.2(4) . . . . ? C6 C5 C4 C3 0.1(5) . . . . ? C12 C11 C10 C9 -0.7(6) . . . . ? C14 C11 C10 C9 178.0(4) . . . . ?