#------------------------------------------------------------------------------ #$Date: 2022-01-06 23:31:01 +0200 (Thu, 06 Jan 2022) $ #$Revision: 271851 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/38/7243895.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_7243895 loop_ _publ_author_name 'Guo, Sheng-Qiang' 'Yang, Hui-Qing' 'Wang, Ai-Lian' 'Jiang, Yu-Zhen' 'Xu, Guo-Qiang' 'Luo, Yong-Chun' 'Chen, Zhao-Xu' 'Xu, Peng-Fei' _publ_section_title ; Divergent Ritter-type amination via photoredox catalytic four-component radical-polar crossover reactions ; _journal_issue 23 _journal_name_full 'Green Chemistry' _journal_page_first 9571 _journal_page_last 9576 _journal_paper_doi 10.1039/D1GC03048E _journal_volume 23 _journal_year 2021 _chemical_formula_moiety 'C25 H25 N O4 S' _chemical_formula_sum 'C25 H25 N O4 S' _chemical_formula_weight 435.52 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-I 2ya' _space_group_name_H-M_alt 'I 1 2/a 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2020-12-29 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226) ; _audit_update_record ; 2021-03-28 deposited with the CCDC. 2021-10-25 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 109.6714(18) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 19.8661(3) _cell_length_b 9.09317(15) _cell_length_c 25.7813(4) _cell_measurement_reflns_used 8979 _cell_measurement_temperature 150.0(2) _cell_measurement_theta_max 75.5340 _cell_measurement_theta_min 3.6380 _cell_volume 4385.48(13) _computing_cell_refinement 'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)' _computing_data_collection 'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)' _computing_data_reduction 'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 150.0(2) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.947 _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 -14.00 21.00 1.00 0.10 -- 43.05 -19.00 -60.00 35 2 \w -26.00 7.00 1.00 0.10 -- 43.05 -37.00 -60.00 33 3 \w -2.00 76.00 1.00 0.10 -- 43.05-103.00 58.00 78 4 \w 63.00 107.00 1.00 0.10 -- 109.26-103.00 58.00 44 5 \w 77.00 102.00 1.00 0.10 -- 109.26 -77.00 90.00 25 6 \w 37.00 67.00 1.00 0.10 -- 109.26 -61.00 120.00 30 7 \w 40.00 68.00 1.00 0.10 -- 109.26 -77.00 90.00 28 8 \w 35.00 60.00 1.00 0.10 -- 109.26 -61.00 60.00 25 9 \w 36.00 64.00 1.00 0.10 -- 109.26 -61.00 -60.00 28 10 \w 35.00 68.00 1.00 0.10 -- 109.26 -61.00-120.00 33 11 \w 37.00 63.00 1.00 0.10 -- 109.26 -61.00 -90.00 26 12 \w 42.00 68.00 1.00 0.10 -- 109.26 -61.00-150.00 26 13 \w 35.00 66.00 1.00 0.10 -- 109.26 -61.00-180.00 31 14 \w 26.00 112.00 1.00 0.10 -- 43.05 57.00-120.00 86 15 \w 87.00 166.00 1.00 0.10 -- 109.26 103.00 160.00 79 16 \w -49.00 -24.00 1.00 0.10 -- -100.00 45.00 150.00 25 17 \w -52.00 -25.00 1.00 0.10 -- -100.00 45.00 90.00 27 18 \w -50.00 -25.00 1.00 0.10 -- -100.00 45.00 30.00 25 19 \w -50.00 -24.00 1.00 0.10 -- -100.00 45.00 -30.00 26 20 \w -54.00 -29.00 1.00 0.10 -- -100.00 45.00 0.00 25 21 \w -67.00 -39.00 1.00 0.10 -- -100.00 61.00 -60.00 28 22 \w -54.00 -27.00 1.00 0.10 -- -100.00 45.00 -90.00 27 23 \w -73.00 -44.00 1.00 0.10 -- -100.00 61.00 0.00 29 24 \w -73.00 -33.00 1.00 0.10 -- -100.00 61.00 120.00 40 25 \w -74.00 -49.00 1.00 0.10 -- -100.00 61.00 150.00 25 26 \w -70.00 -3.00 1.00 0.10 -- -43.05 103.00 160.00 67 27 \w -106.00 -51.00 1.00 0.10 -- -100.00 103.00 160.00 55 28 \w -149.00 -90.00 1.00 0.10 -- -100.00 -94.00 90.00 59 29 \w -152.00-108.00 1.00 0.10 -- -100.00-103.00 58.00 44 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'ROD, Synergy Custom system, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0289302000 _diffrn_orient_matrix_UB_12 -0.0556424000 _diffrn_orient_matrix_UB_13 0.0599084000 _diffrn_orient_matrix_UB_21 -0.0121411000 _diffrn_orient_matrix_UB_22 0.1533416000 _diffrn_orient_matrix_UB_23 0.0206439000 _diffrn_orient_matrix_UB_31 -0.0761133000 _diffrn_orient_matrix_UB_32 -0.0457305000 _diffrn_orient_matrix_UB_33 -0.0035850000 _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 0.0446 _diffrn_reflns_av_unetI/netI 0.0379 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.947 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 13779 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.947 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 75.911 _diffrn_reflns_theta_min 3.641 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.573 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.07487 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.319 _exptl_crystal_description block _exptl_crystal_F_000 1840 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.353 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.054 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 283 _refine_ls_number_reflns 4342 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.063 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0446 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0776P)^2^+1.9746P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1253 _refine_ls_wR_factor_ref 0.1279 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3926 _reflns_number_total 4342 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1gc03048e2.cif _cod_data_source_block guoshq_1229 _cod_depositor_comments 'Adding full bibliography for 7243893--7243896.cif.' _cod_database_code 7243895 _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 0.898 _shelx_estimated_absorpt_t_min 0.810 _reflns_odcompleteness_completeness 99.83 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _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 2.a Ternary CH refined with riding coordinates: C10(H10), C17(H17) 2.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C20(H20), C21(H21), C23(H23), C24(H24) 2.c Idealised Me refined as rotating group: C9(H9A,H9B,H9C), C18(H18A,H18B,H18C), C25(H25A,H25B,H25C) ; _shelx_res_file ; TITL guoshq_1229_a.res in I2/a guoshq_1229.res created by SHELXL-2018/3 at 18:18:37 on 29-Dec-2020 REM Old TITL guoshq_1229 in I2/a REM SHELXT solution in I2/a: R1 0.132, Rweak 0.086, Alpha 0.028 REM 1.030 for 275 systematic absences, Orientation as input REM Formula found by SHELXT: C25 N O4 S CELL 1.54184 19.866126 9.09317 25.781299 90 109.6714 90 ZERR 8 0.000321 0.00015 0.000426 0 0.0018 0 LATT 2 SYMM 0.5-X,+Y,-Z SFAC C H N O S UNIT 200 200 8 32 8 L.S. 4 0 0 PLAN 1 SIZE 0.07 0.12 0.14 CONF BOND list 4 MORE -1 BOND $H fmap 2 53 ACTA REM REM REM WGHT 0.077600 1.974600 FVAR 2.96181 S1 5 0.521820 1.056497 0.679612 11.00000 0.03590 0.03557 = 0.03466 -0.00728 0.01008 -0.01128 O1 4 0.432305 0.586739 0.610181 11.00000 0.04638 0.02937 = 0.02939 0.00294 0.00263 0.00358 O2 4 0.417579 0.976203 0.497797 11.00000 0.03800 0.03150 = 0.03252 0.00484 0.00728 0.00066 O3 4 0.594205 1.045025 0.716881 11.00000 0.03149 0.06665 = 0.05044 -0.02014 0.01046 -0.01665 O4 4 0.504400 1.170947 0.638447 11.00000 0.07438 0.03413 = 0.04072 -0.00323 0.02246 -0.01624 N1 3 0.416004 0.785235 0.553956 11.00000 0.02992 0.02622 = 0.02596 -0.00091 0.00622 0.00055 C1 1 0.366434 0.539993 0.516877 11.00000 0.02439 0.02707 = 0.02913 -0.00007 0.00986 0.00092 C2 1 0.378846 0.389642 0.521418 11.00000 0.03117 0.02893 = 0.03251 0.00229 0.00988 0.00490 AFIX 43 H2 2 0.414654 0.351932 0.551902 11.00000 -1.20000 AFIX 0 C3 1 0.338150 0.295658 0.480765 11.00000 0.04581 0.02542 = 0.04348 -0.00315 0.01368 0.00089 AFIX 43 H3 2 0.347190 0.195095 0.483505 11.00000 -1.20000 AFIX 0 C4 1 0.283670 0.351943 0.435776 11.00000 0.04095 0.03896 = 0.03583 -0.00731 0.00959 -0.00822 AFIX 43 H4 2 0.256162 0.288712 0.408504 11.00000 -1.20000 AFIX 0 C5 1 0.270248 0.500638 0.431395 11.00000 0.02832 0.04188 = 0.03075 -0.00006 0.00579 0.00012 AFIX 43 H5 2 0.233453 0.537541 0.401381 11.00000 -1.20000 AFIX 0 C6 1 0.311588 0.595771 0.471752 11.00000 0.02884 0.02734 = 0.03261 0.00278 0.00954 0.00406 AFIX 43 H6 2 0.302708 0.696377 0.468681 11.00000 -1.20000 AFIX 0 C7 1 0.408804 0.634805 0.563498 11.00000 0.02726 0.02646 = 0.03031 -0.00021 0.00722 0.00398 C8 1 0.424849 0.845478 0.506357 11.00000 0.02268 0.03246 = 0.02695 0.00124 0.00413 -0.00183 C9 1 0.449442 0.748299 0.469184 11.00000 0.03824 0.03928 = 0.03967 -0.00141 0.01926 -0.00170 AFIX 137 H9A 2 0.410584 0.732066 0.435466 11.00000 -1.50000 H9B 2 0.465236 0.655768 0.487068 11.00000 -1.50000 H9C 2 0.488232 0.794913 0.461245 11.00000 -1.50000 AFIX 0 C10 1 0.422986 0.888744 0.600434 11.00000 0.02866 0.02438 = 0.02718 -0.00186 0.00542 -0.00018 AFIX 13 H10 2 0.418811 0.987652 0.584561 11.00000 -1.20000 AFIX 0 C11 1 0.359975 0.872427 0.621134 11.00000 0.02641 0.02443 = 0.02670 -0.00416 0.00315 -0.00161 C12 1 0.361435 0.789344 0.666681 11.00000 0.02653 0.02634 = 0.03132 -0.00150 0.00240 -0.00103 AFIX 43 H12 2 0.402480 0.736930 0.685844 11.00000 -1.20000 AFIX 0 C13 1 0.302411 0.783424 0.684030 11.00000 0.03229 0.03410 = 0.03335 -0.00079 0.00717 -0.00517 AFIX 43 H13 2 0.304375 0.728338 0.714900 11.00000 -1.20000 AFIX 0 C14 1 0.240325 0.859881 0.655246 11.00000 0.02581 0.04289 = 0.04031 -0.00646 0.00835 -0.00564 AFIX 43 H14 2 0.200729 0.855996 0.666745 11.00000 -1.20000 AFIX 0 C15 1 0.237975 0.941633 0.609436 11.00000 0.02493 0.03773 = 0.03714 -0.00400 -0.00033 0.00322 AFIX 43 H15 2 0.196545 0.992455 0.589958 11.00000 -1.20000 AFIX 0 C16 1 0.297109 0.948198 0.592399 11.00000 0.03031 0.03026 = 0.02726 -0.00099 0.00111 0.00036 AFIX 43 H16 2 0.294977 1.003538 0.561549 11.00000 -1.20000 AFIX 0 C17 1 0.499108 0.880933 0.644533 11.00000 0.02726 0.02967 = 0.02992 -0.00178 0.00564 -0.00307 AFIX 13 H17 2 0.499974 0.804250 0.671460 11.00000 -1.20000 AFIX 0 C18 1 0.557576 0.849626 0.619528 11.00000 0.02834 0.04257 = 0.03880 -0.00180 0.00941 0.00085 AFIX 137 H18A 2 0.552411 0.915867 0.589437 11.00000 -1.50000 H18B 2 0.553255 0.750116 0.606371 11.00000 -1.50000 H18C 2 0.603678 0.863290 0.647117 11.00000 -1.50000 AFIX 0 C19 1 0.465076 1.073760 0.718773 11.00000 0.03180 0.02920 = 0.02831 -0.00617 0.00430 -0.00507 C20 1 0.479602 0.993884 0.767222 11.00000 0.03192 0.03283 = 0.02923 -0.00405 0.00071 -0.00050 AFIX 43 H20 2 0.522011 0.941157 0.781134 11.00000 -1.20000 AFIX 0 C21 1 0.430764 0.993299 0.794526 11.00000 0.04162 0.03742 = 0.02977 -0.00419 0.00644 -0.00539 AFIX 43 H21 2 0.440372 0.939447 0.826882 11.00000 -1.20000 AFIX 0 C22 1 0.367226 1.072215 0.774345 11.00000 0.03931 0.04009 = 0.04187 -0.01219 0.01220 -0.00376 C23 1 0.355387 1.156956 0.727237 11.00000 0.03886 0.03868 = 0.04800 -0.00548 0.00650 0.00830 AFIX 43 H23 2 0.314324 1.214321 0.714555 11.00000 -1.20000 AFIX 0 C24 1 0.403163 1.157922 0.698857 11.00000 0.04223 0.02915 = 0.03529 -0.00130 0.00288 0.00150 AFIX 43 H24 2 0.394161 1.213767 0.667016 11.00000 -1.20000 AFIX 0 C25 1 0.312024 1.063859 0.802460 11.00000 0.05267 0.06951 = 0.06816 -0.01526 0.03022 -0.00565 AFIX 137 H25A 2 0.327457 0.995210 0.832441 11.00000 -1.50000 H25B 2 0.267293 1.031821 0.776525 11.00000 -1.50000 H25C 2 0.306141 1.159220 0.816330 11.00000 -1.50000 AFIX 0 HKLF 4 REM guoshq_1229_a.res in I2/a REM wR2 = 0.1279, GooF = S = 1.063, Restrained GooF = 1.063 for all data REM R1 = 0.0446 for 3926 Fo > 4sig(Fo) and 0.0481 for all 4342 data REM 283 parameters refined using 0 restraints END WGHT 0.0776 1.9746 REM Highest difference peak 0.353, deepest hole -0.411, 1-sigma level 0.054 Q1 1 0.4875 1.0619 0.6982 11.00000 0.05 0.35 ; _shelx_res_checksum 78772 _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 9.271 _oxdiff_exptl_absorpt_empirical_full_min 0.440 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' '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 S1 S 0.52182(2) 1.05650(5) 0.67961(2) 0.03583(14) Uani 1 1 d . . . . . O1 O 0.43231(6) 0.58674(13) 0.61018(5) 0.0376(3) Uani 1 1 d . . . . . O2 O 0.41758(6) 0.97620(13) 0.49780(5) 0.0352(3) Uani 1 1 d . . . . . O3 O 0.59421(6) 1.04502(17) 0.71688(6) 0.0504(4) Uani 1 1 d . . . . . O4 O 0.50440(8) 1.17095(15) 0.63845(5) 0.0490(3) Uani 1 1 d . . . . . N1 N 0.41600(6) 0.78524(14) 0.55396(5) 0.0282(3) Uani 1 1 d . . . . . C1 C 0.36643(7) 0.53999(16) 0.51688(6) 0.0266(3) Uani 1 1 d . . . . . C2 C 0.37885(8) 0.38964(18) 0.52142(6) 0.0311(3) Uani 1 1 d . . . . . H2 H 0.414654 0.351932 0.551902 0.037 Uiso 1 1 calc R U . . . C3 C 0.33815(9) 0.29566(19) 0.48077(7) 0.0386(4) Uani 1 1 d . . . . . H3 H 0.347190 0.195095 0.483505 0.046 Uiso 1 1 calc R U . . . C4 C 0.28367(9) 0.3519(2) 0.43578(7) 0.0394(4) Uani 1 1 d . . . . . H4 H 0.256162 0.288712 0.408504 0.047 Uiso 1 1 calc R U . . . C5 C 0.27025(8) 0.5006(2) 0.43140(7) 0.0347(4) Uani 1 1 d . . . . . H5 H 0.233453 0.537541 0.401381 0.042 Uiso 1 1 calc R U . . . C6 C 0.31159(8) 0.59577(18) 0.47175(6) 0.0298(3) Uani 1 1 d . . . . . H6 H 0.302708 0.696377 0.468681 0.036 Uiso 1 1 calc R U . . . C7 C 0.40880(7) 0.63481(17) 0.56350(6) 0.0286(3) Uani 1 1 d . . . . . C8 C 0.42485(7) 0.84548(18) 0.50636(6) 0.0284(3) Uani 1 1 d . . . . . C9 C 0.44944(9) 0.7483(2) 0.46918(7) 0.0375(4) Uani 1 1 d . . . . . H9A H 0.410584 0.732066 0.435466 0.056 Uiso 1 1 calc R U . . . H9B H 0.465236 0.655768 0.487068 0.056 Uiso 1 1 calc R U . . . H9C H 0.488232 0.794913 0.461245 0.056 Uiso 1 1 calc R U . . . C10 C 0.42299(8) 0.88874(17) 0.60043(6) 0.0277(3) Uani 1 1 d . . . . . H10 H 0.418811 0.987652 0.584561 0.033 Uiso 1 1 calc R U . . . C11 C 0.35998(7) 0.87243(17) 0.62113(6) 0.0273(3) Uani 1 1 d . . . . . C12 C 0.36143(8) 0.78934(17) 0.66668(6) 0.0299(3) Uani 1 1 d . . . . . H12 H 0.402480 0.736930 0.685844 0.036 Uiso 1 1 calc R U . . . C13 C 0.30241(8) 0.78342(19) 0.68403(7) 0.0342(3) Uani 1 1 d . . . . . H13 H 0.304375 0.728338 0.714900 0.041 Uiso 1 1 calc R U . . . C14 C 0.24032(8) 0.8599(2) 0.65525(7) 0.0370(4) Uani 1 1 d . . . . . H14 H 0.200729 0.855996 0.666745 0.044 Uiso 1 1 calc R U . . . C15 C 0.23798(8) 0.94163(19) 0.60944(7) 0.0360(4) Uani 1 1 d . . . . . H15 H 0.196545 0.992455 0.589958 0.043 Uiso 1 1 calc R U . . . C16 C 0.29711(8) 0.94820(18) 0.59240(6) 0.0314(3) Uani 1 1 d . . . . . H16 H 0.294977 1.003538 0.561549 0.038 Uiso 1 1 calc R U . . . C17 C 0.49911(8) 0.88093(18) 0.64453(6) 0.0300(3) Uani 1 1 d . . . . . H17 H 0.499974 0.804250 0.671460 0.036 Uiso 1 1 calc R U . . . C18 C 0.55758(8) 0.8496(2) 0.61953(7) 0.0370(4) Uani 1 1 d . . . . . H18A H 0.552411 0.915867 0.589437 0.056 Uiso 1 1 calc R U . . . H18B H 0.553255 0.750116 0.606371 0.056 Uiso 1 1 calc R U . . . H18C H 0.603678 0.863290 0.647117 0.056 Uiso 1 1 calc R U . . . C19 C 0.46508(8) 1.07376(18) 0.71877(6) 0.0312(3) Uani 1 1 d . . . . . C20 C 0.47960(8) 0.99388(19) 0.76722(6) 0.0338(3) Uani 1 1 d . . . . . H20 H 0.522011 0.941157 0.781134 0.041 Uiso 1 1 calc R U . . . C21 C 0.43076(9) 0.9933(2) 0.79453(7) 0.0377(4) Uani 1 1 d . . . . . H21 H 0.440372 0.939447 0.826882 0.045 Uiso 1 1 calc R U . . . C22 C 0.36723(9) 1.0722(2) 0.77435(8) 0.0408(4) Uani 1 1 d . . . . . C23 C 0.35539(9) 1.1570(2) 0.72724(8) 0.0439(4) Uani 1 1 d . . . . . H23 H 0.314324 1.214321 0.714555 0.053 Uiso 1 1 calc R U . . . C24 C 0.40316(9) 1.15792(19) 0.69886(7) 0.0381(4) Uani 1 1 d . . . . . H24 H 0.394161 1.213767 0.667016 0.046 Uiso 1 1 calc R U . . . C25 C 0.31202(12) 1.0639(3) 0.80246(11) 0.0609(6) Uani 1 1 d . . . . . H25A H 0.327457 0.995210 0.832441 0.091 Uiso 1 1 calc R U . . . H25B H 0.267293 1.031821 0.776525 0.091 Uiso 1 1 calc R U . . . H25C H 0.306141 1.159220 0.816330 0.091 Uiso 1 1 calc R U . . . 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 0.0359(2) 0.0356(3) 0.0347(2) -0.00728(16) 0.01008(17) -0.01128(15) O1 0.0464(7) 0.0294(6) 0.0294(6) 0.0029(5) 0.0026(5) 0.0036(5) O2 0.0380(6) 0.0315(6) 0.0325(6) 0.0048(5) 0.0073(5) 0.0007(5) O3 0.0315(6) 0.0667(10) 0.0504(8) -0.0201(7) 0.0105(6) -0.0166(6) O4 0.0744(9) 0.0341(7) 0.0407(7) -0.0032(5) 0.0225(6) -0.0162(6) N1 0.0299(6) 0.0262(7) 0.0260(6) -0.0009(5) 0.0062(5) 0.0006(5) C1 0.0244(6) 0.0271(8) 0.0291(7) -0.0001(6) 0.0099(6) 0.0009(5) C2 0.0312(7) 0.0289(8) 0.0325(8) 0.0023(6) 0.0099(6) 0.0049(6) C3 0.0458(9) 0.0254(8) 0.0435(9) -0.0032(7) 0.0137(7) 0.0009(7) C4 0.0410(9) 0.0390(10) 0.0358(8) -0.0073(7) 0.0096(7) -0.0082(7) C5 0.0283(7) 0.0419(10) 0.0307(8) -0.0001(7) 0.0058(6) 0.0001(7) C6 0.0288(7) 0.0273(8) 0.0326(8) 0.0028(6) 0.0095(6) 0.0041(6) C7 0.0273(7) 0.0265(8) 0.0303(7) -0.0002(6) 0.0072(6) 0.0040(6) C8 0.0227(6) 0.0325(8) 0.0269(7) 0.0012(6) 0.0041(5) -0.0018(6) C9 0.0382(8) 0.0393(9) 0.0397(9) -0.0014(7) 0.0193(7) -0.0017(7) C10 0.0287(7) 0.0244(7) 0.0272(7) -0.0019(6) 0.0054(6) -0.0002(5) C11 0.0264(7) 0.0244(7) 0.0267(7) -0.0042(6) 0.0032(5) -0.0016(5) C12 0.0265(7) 0.0263(8) 0.0313(7) -0.0015(6) 0.0024(6) -0.0010(6) C13 0.0323(8) 0.0341(9) 0.0334(8) -0.0008(7) 0.0072(6) -0.0052(6) C14 0.0258(7) 0.0429(10) 0.0403(9) -0.0065(7) 0.0083(6) -0.0056(7) C15 0.0249(7) 0.0377(9) 0.0371(9) -0.0040(7) -0.0003(6) 0.0032(6) C16 0.0303(7) 0.0303(8) 0.0273(7) -0.0010(6) 0.0011(6) 0.0004(6) C17 0.0273(7) 0.0297(8) 0.0299(7) -0.0018(6) 0.0056(6) -0.0031(6) C18 0.0283(7) 0.0426(10) 0.0388(9) -0.0018(7) 0.0094(6) 0.0009(7) C19 0.0318(8) 0.0292(8) 0.0283(7) -0.0062(6) 0.0043(6) -0.0051(6) C20 0.0319(8) 0.0328(9) 0.0292(8) -0.0041(7) 0.0007(6) -0.0005(6) C21 0.0416(9) 0.0374(9) 0.0298(8) -0.0042(7) 0.0064(7) -0.0054(7) C22 0.0393(9) 0.0401(10) 0.0419(9) -0.0122(8) 0.0122(7) -0.0038(7) C23 0.0389(9) 0.0387(10) 0.0480(10) -0.0055(8) 0.0065(7) 0.0083(7) C24 0.0422(9) 0.0291(9) 0.0353(8) -0.0013(7) 0.0029(7) 0.0015(7) C25 0.0527(12) 0.0695(15) 0.0682(14) -0.0153(12) 0.0302(11) -0.0057(10) 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 O3 S1 O4 118.79(9) . . ? O3 S1 C17 107.08(8) . . ? O3 S1 C19 108.26(8) . . ? O4 S1 C17 108.06(7) . . ? O4 S1 C19 108.49(8) . . ? C19 S1 C17 105.38(7) . . ? C7 N1 C8 125.53(13) . . ? C7 N1 C10 117.42(12) . . ? C8 N1 C10 116.69(12) . . ? C2 C1 C6 119.71(14) . . ? C2 C1 C7 117.81(13) . . ? C6 C1 C7 122.26(14) . . ? C1 C2 H2 119.9 . . ? C3 C2 C1 120.21(15) . . ? C3 C2 H2 119.9 . . ? C2 C3 H3 120.1 . . ? C2 C3 C4 119.81(16) . . ? C4 C3 H3 120.1 . . ? C3 C4 H4 119.8 . . ? C5 C4 C3 120.35(16) . . ? C5 C4 H4 119.8 . . ? C4 C5 H5 120.0 . . ? C4 C5 C6 120.08(15) . . ? C6 C5 H5 120.0 . . ? C1 C6 H6 120.1 . . ? C5 C6 C1 119.82(15) . . ? C5 C6 H6 120.1 . . ? O1 C7 N1 119.68(14) . . ? O1 C7 C1 121.02(14) . . ? N1 C7 C1 119.05(13) . . ? O2 C8 N1 119.96(14) . . ? O2 C8 C9 120.46(14) . . ? N1 C8 C9 119.37(14) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 H10 105.8 . . ? N1 C10 C11 110.75(12) . . ? N1 C10 C17 111.23(12) . . ? C11 C10 H10 105.8 . . ? C11 C10 C17 116.74(12) . . ? C17 C10 H10 105.8 . . ? C12 C11 C10 124.28(13) . . ? C12 C11 C16 118.44(14) . . ? C16 C11 C10 117.27(14) . . ? C11 C12 H12 119.5 . . ? C11 C12 C13 120.91(14) . . ? C13 C12 H12 119.5 . . ? C12 C13 H13 120.0 . . ? C12 C13 C14 120.07(15) . . ? C14 C13 H13 120.0 . . ? C13 C14 H14 120.2 . . ? C15 C14 C13 119.52(15) . . ? C15 C14 H14 120.2 . . ? C14 C15 H15 119.8 . . ? C14 C15 C16 120.32(15) . . ? C16 C15 H15 119.8 . . ? C11 C16 H16 119.6 . . ? C15 C16 C11 120.73(15) . . ? C15 C16 H16 119.6 . . ? S1 C17 H17 109.3 . . ? C10 C17 S1 109.93(11) . . ? C10 C17 H17 109.3 . . ? C18 C17 S1 106.04(11) . . ? C18 C17 C10 112.85(12) . . ? C18 C17 H17 109.3 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 S1 119.43(12) . . ? C20 C19 C24 120.64(16) . . ? C24 C19 S1 119.73(13) . . ? C19 C20 H20 120.2 . . ? C21 C20 C19 119.53(15) . . ? C21 C20 H20 120.2 . . ? C20 C21 H21 119.6 . . ? C20 C21 C22 120.88(17) . . ? C22 C21 H21 119.6 . . ? C21 C22 C25 120.65(19) . . ? C23 C22 C21 118.55(17) . . ? C23 C22 C25 120.80(18) . . ? C22 C23 H23 119.2 . . ? C24 C23 C22 121.51(16) . . ? C24 C23 H23 119.2 . . ? C19 C24 H24 120.6 . . ? C23 C24 C19 118.76(16) . . ? C23 C24 H24 120.6 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25B 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 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 O3 1.4394(13) . ? S1 O4 1.4429(14) . ? S1 C17 1.8153(17) . ? S1 C19 1.7553(16) . ? O1 C7 1.2162(19) . ? O2 C8 1.209(2) . ? N1 C7 1.406(2) . ? N1 C8 1.4079(19) . ? N1 C10 1.4930(19) . ? C1 C2 1.387(2) . ? C1 C6 1.394(2) . ? C1 C7 1.488(2) . ? C2 H2 0.9300 . ? C2 C3 1.383(2) . ? C3 H3 0.9300 . ? C3 C4 1.391(2) . ? C4 H4 0.9300 . ? C4 C5 1.375(3) . ? C5 H5 0.9300 . ? C5 C6 1.389(2) . ? C6 H6 0.9300 . ? C8 C9 1.501(2) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10 0.9800 . ? C10 C11 1.524(2) . ? C10 C17 1.5579(19) . ? C11 C12 1.388(2) . ? C11 C16 1.400(2) . ? C12 H12 0.9300 . ? C12 C13 1.390(2) . ? C13 H13 0.9300 . ? C13 C14 1.393(2) . ? C14 H14 0.9300 . ? C14 C15 1.383(3) . ? C15 H15 0.9300 . ? C15 C16 1.387(2) . ? C16 H16 0.9300 . ? C17 H17 0.9800 . ? C17 C18 1.533(2) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.389(2) . ? C19 C24 1.392(2) . ? C20 H20 0.9300 . ? C20 C21 1.377(2) . ? C21 H21 0.9300 . ? C21 C22 1.392(3) . ? C22 C23 1.390(3) . ? C22 C25 1.506(3) . ? C23 H23 0.9300 . ? C23 C24 1.380(3) . ? C24 H24 0.9300 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 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 C19 C20 C21 -172.21(13) . . . . ? S1 C19 C24 C23 172.92(13) . . . . ? O3 S1 C17 C10 -176.12(10) . . . . ? O3 S1 C17 C18 -53.84(13) . . . . ? O3 S1 C19 C20 -38.12(15) . . . . ? O3 S1 C19 C24 146.93(13) . . . . ? O4 S1 C17 C10 -47.06(12) . . . . ? O4 S1 C17 C18 75.23(12) . . . . ? O4 S1 C19 C20 -168.29(12) . . . . ? O4 S1 C19 C24 16.76(15) . . . . ? N1 C10 C11 C12 97.89(16) . . . . ? N1 C10 C11 C16 -82.95(17) . . . . ? N1 C10 C17 S1 151.65(10) . . . . ? N1 C10 C17 C18 33.49(18) . . . . ? C1 C2 C3 C4 -1.3(2) . . . . ? C2 C1 C6 C5 -0.7(2) . . . . ? C2 C1 C7 O1 -26.9(2) . . . . ? C2 C1 C7 N1 158.96(13) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C3 C4 C5 C6 0.6(2) . . . . ? C4 C5 C6 C1 -0.4(2) . . . . ? C6 C1 C2 C3 1.5(2) . . . . ? C6 C1 C7 O1 147.78(15) . . . . ? C6 C1 C7 N1 -26.4(2) . . . . ? C7 N1 C8 O2 166.57(13) . . . . ? C7 N1 C8 C9 -18.7(2) . . . . ? C7 N1 C10 C11 -56.09(16) . . . . ? C7 N1 C10 C17 75.45(16) . . . . ? C7 C1 C2 C3 176.28(14) . . . . ? C7 C1 C6 C5 -175.18(14) . . . . ? C8 N1 C7 O1 147.40(15) . . . . ? C8 N1 C7 C1 -38.3(2) . . . . ? C8 N1 C10 C11 130.45(13) . . . . ? C8 N1 C10 C17 -98.00(14) . . . . ? C10 N1 C7 O1 -25.4(2) . . . . ? C10 N1 C7 C1 148.86(13) . . . . ? C10 N1 C8 O2 -20.58(19) . . . . ? C10 N1 C8 C9 154.19(13) . . . . ? C10 C11 C12 C13 178.02(14) . . . . ? C10 C11 C16 C15 -178.51(14) . . . . ? C11 C10 C17 S1 -79.95(15) . . . . ? C11 C10 C17 C18 161.89(14) . . . . ? C11 C12 C13 C14 0.8(2) . . . . ? C12 C11 C16 C15 0.7(2) . . . . ? C12 C13 C14 C15 -0.1(3) . . . . ? C13 C14 C15 C16 -0.3(3) . . . . ? C14 C15 C16 C11 0.0(2) . . . . ? C16 C11 C12 C13 -1.1(2) . . . . ? C17 S1 C19 C20 76.18(14) . . . . ? C17 S1 C19 C24 -98.77(14) . . . . ? C17 C10 C11 C12 -30.7(2) . . . . ? C17 C10 C11 C16 148.42(14) . . . . ? C19 S1 C17 C10 68.77(12) . . . . ? C19 S1 C17 C18 -168.95(11) . . . . ? C19 C20 C21 C22 -0.3(3) . . . . ? C20 C19 C24 C23 -2.0(2) . . . . ? C20 C21 C22 C23 -2.7(3) . . . . ? C20 C21 C22 C25 176.27(17) . . . . ? C21 C22 C23 C24 3.5(3) . . . . ? C22 C23 C24 C19 -1.2(3) . . . . ? C24 C19 C20 C21 2.7(2) . . . . ? C25 C22 C23 C24 -175.52(18) . . . . ?