#------------------------------------------------------------------------------ #$Date: 2021-10-06 19:13:14 +0300 (Wed, 06 Oct 2021) $ #$Revision: 269772 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/82/7158296.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_7158296 loop_ _publ_author_name 'Bormann, Carl Thomas' 'Fadaei-Tirani, Farzaneh' 'Scopelliti, Rosario' 'Severin, Kay' _publ_section_title ; Synthesis of bicyclic vinyl triazenes by Ficini-type reactions. ; _journal_issue 37 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 8113 _journal_page_last 8117 _journal_paper_doi 10.1039/d1ob01546j _journal_volume 19 _journal_year 2021 _chemical_formula_moiety 'C26 H36 N4 O3 S' _chemical_formula_sum 'C26 H36 N4 O3 S' _chemical_formula_weight 484.65 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_date 2021-05-07 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) ; _audit_update_record ; 2021-08-03 deposited with the CCDC. 2021-09-02 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 95.7493(9) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.80574(8) _cell_length_b 34.1537(3) _cell_length_c 9.62710(9) _cell_measurement_reflns_used 12502 _cell_measurement_temperature 140.00(10) _cell_measurement_theta_max 72.5600 _cell_measurement_theta_min 4.7730 _cell_volume 2553.63(4) _computing_cell_refinement 'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)' _computing_data_collection 'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)' _computing_data_reduction 'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)' _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 2018/2 (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 140.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2817 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.986 _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 -89.00 -64.00 1.00 2.00 -- -40.91 155.00 -71.00 25 2 \w -111.00 -86.00 1.00 2.00 -- -40.91-155.00-110.00 25 3 \w -68.00 -43.00 1.00 2.00 -- -40.91 120.00 131.00 25 4 \w 56.00 81.00 1.00 2.00 -- 40.91-120.00 47.00 25 5 \w 46.00 73.00 1.00 8.00 -- 105.15-120.00 47.00 27 6 \w 93.00 142.00 1.00 8.00 -- 105.15 155.00 -71.00 49 7 \w 120.00 146.00 1.00 8.00 -- 105.15 120.00 131.00 26 8 \w 64.00 89.00 1.00 8.00 -- 105.15-155.00-110.00 25 9 \w -114.00 -17.00 1.00 2.00 -- -40.91 -38.00 -60.00 97 10 \w -86.00 -10.00 1.00 2.00 -- -40.91 125.00-180.00 76 11 \w -106.00 -16.00 1.00 2.00 -- -40.91 -38.00 30.00 90 12 \w 49.00 74.00 1.00 2.00 -- 40.91-125.00 -90.00 25 13 \w -21.00 50.00 1.00 2.00 -- 40.91 -77.00 150.00 71 14 \w 135.00 161.00 1.00 8.00 -- 105.15 111.00-120.00 26 15 \w 34.00 70.00 1.00 8.00 -- 105.15-111.00 -60.00 36 16 \w 80.00 178.00 1.00 8.00 -- 105.15 45.00 120.00 98 17 \w 29.00 109.00 1.00 8.00 -- 105.15-111.00 120.00 80 18 \w 31.00 130.00 1.00 8.00 -- 105.15 -77.00 -60.00 99 19 \w 23.00 98.00 1.00 8.00 -- 105.15 -94.00-120.00 75 20 \w 84.00 109.00 1.00 8.00 -- 105.15-111.00 -60.00 25 21 \w 57.00 108.00 1.00 8.00 -- 105.15-111.00 0.00 51 22 \w 43.00 109.00 1.00 8.00 -- 105.15-111.00-180.00 66 23 \w 82.00 178.00 1.00 8.00 -- 105.15 30.00-180.00 96 24 \w 104.00 144.00 1.00 8.00 -- 105.15 111.00 0.00 40 25 \w 76.00 176.00 1.00 8.00 -- 105.15 61.00 60.00 100 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.1973596000 _diffrn_orient_matrix_UB_12 0.0007047000 _diffrn_orient_matrix_UB_13 -0.0001307000 _diffrn_orient_matrix_UB_21 0.0006201000 _diffrn_orient_matrix_UB_22 0.0447647000 _diffrn_orient_matrix_UB_23 -0.0196589000 _diffrn_orient_matrix_UB_31 -0.0198985000 _diffrn_orient_matrix_UB_32 -0.0055030000 _diffrn_orient_matrix_UB_33 -0.1596238000 _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 0.0222 _diffrn_reflns_av_unetI/netI 0.0171 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.986 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 20995 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.986 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 72.655 _diffrn_reflns_theta_min 4.795 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.400 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.640 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021) Numerical absorption correction based on Gaussian integration over a multifaceted crystal model. Empirical absorption correction using spherical harmonics as implemented in SCALE3 ABSPACK scaling algorithm ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.261 _exptl_crystal_description plate _exptl_crystal_F_000 1040 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.303 _refine_diff_density_min -0.348 _refine_diff_density_rms 0.036 _refine_ls_extinction_coef 0.00059(10) _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 1.022 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 314 _refine_ls_number_reflns 5004 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.022 _refine_ls_R_factor_all 0.0330 _refine_ls_R_factor_gt 0.0310 _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^)+(0.0405P)^2^+0.9103P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0799 _refine_ls_wR_factor_ref 0.0816 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4698 _reflns_number_total 5004 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01546j2.cif _cod_data_source_block cb715-1 _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Gaussian' was changed to 'gaussian' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas Adding full bibliography for 7158295--7158296.cif. ; _cod_original_cell_volume 2553.62(4) _cod_database_code 7158296 _shelx_shelxl_version_number 2018/3 _audit_contact_author 'Farzaneh Fadaei Tirani' _chemical_oxdiff_formula 'C26 H36 N4 O3 S' _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 0.959 _shelx_estimated_absorpt_t_min 0.712 _reflns_odcompleteness_completeness 99.96 _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.a Ternary CH refined with riding coordinates: C2(H2), C21(H21), C24(H24) 2.b Secondary CH2 refined with riding coordinates: C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B) 2.c Aromatic/amide H refined with riding coordinates: C10(H10), C15(H15), C16(H16), C18(H18), C19(H19) 2.d Idealised Me refined as rotating group: C8(H8A,H8B,H8C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C23(H23A,H23B, H23C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C) ; _shelx_res_file ; TITL cb715-1.res in P2(1)/c cb715-1.res created by SHELXL-2018/3 at 15:36:58 on 07-May-2021 CELL 1.54184 7.805735 34.15366 9.627101 90 95.7493 90 ZERR 4 0.000083 0.000341 0.000089 0 0.0009 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O S UNIT 104 144 16 12 4 L.S. 20 PLAN 10 SIZE 0.03 0.18 0.26 TEMP -133.15 CONF wpdb -2 MORE -1 BOND $H fmap 2 acta REM REM REM WGHT 0.040500 0.910300 EXTI 0.000586 FVAR 0.52111 S1 5 0.642923 0.411913 0.563748 11.00000 0.01824 0.02110 = 0.02738 -0.00326 -0.00123 -0.00082 O1 4 0.401885 0.222515 0.330810 11.00000 0.05085 0.02442 = 0.03627 -0.00549 0.00889 -0.00677 O2 4 0.803098 0.423476 0.514926 11.00000 0.01868 0.02707 = 0.04728 -0.00522 0.00254 -0.00333 O3 4 0.621145 0.413312 0.709904 11.00000 0.03323 0.02852 = 0.02624 -0.00452 -0.00459 0.00065 N1 3 0.612095 0.366584 0.516419 11.00000 0.01986 0.02080 = 0.02503 -0.00242 0.00121 -0.00168 N2 3 0.252506 0.367112 0.271018 11.00000 0.01791 0.02424 = 0.01998 0.00083 -0.00054 0.00144 N3 3 0.107772 0.373932 0.200957 11.00000 0.02018 0.02841 = 0.01958 0.00173 -0.00030 0.00219 N4 3 0.116595 0.393079 0.081750 11.00000 0.01849 0.03434 = 0.02026 0.00531 -0.00019 0.00140 C1 1 0.379945 0.321995 0.454027 11.00000 0.01704 0.02226 = 0.01776 0.00066 -0.00056 -0.00119 C2 1 0.322752 0.278683 0.467906 11.00000 0.02239 0.02335 = 0.02026 0.00182 -0.00128 -0.00274 AFIX 13 H2 2 0.366043 0.269120 0.563177 11.00000 -1.20000 AFIX 0 C3 1 0.419988 0.257002 0.360545 11.00000 0.02623 0.02508 = 0.02235 -0.00075 -0.00260 -0.00106 C4 1 0.544368 0.283961 0.304132 11.00000 0.01995 0.02617 = 0.02351 -0.00315 -0.00112 0.00014 C5 1 0.520467 0.319519 0.356432 11.00000 0.01552 0.02438 = 0.01930 0.00097 -0.00183 0.00033 C6 1 0.630160 0.355301 0.369237 11.00000 0.01715 0.02443 = 0.02540 -0.00218 0.00268 -0.00112 AFIX 23 H6A 2 0.751255 0.349366 0.354823 11.00000 -1.20000 H6B 2 0.585756 0.375933 0.302909 11.00000 -1.20000 AFIX 0 C7 1 0.486651 0.341029 0.580839 11.00000 0.02040 0.02374 = 0.02049 0.00133 -0.00187 -0.00194 AFIX 23 H7A 2 0.412081 0.356668 0.637053 11.00000 -1.20000 H7B 2 0.547004 0.320865 0.641302 11.00000 -1.20000 AFIX 0 C8 1 0.678939 0.270546 0.214846 11.00000 0.02721 0.03418 = 0.03907 -0.01192 0.00782 -0.00180 AFIX 137 H8A 2 0.632786 0.271602 0.116429 11.00000 -1.50000 H8B 2 0.712387 0.243589 0.239653 11.00000 -1.50000 H8C 2 0.779896 0.287651 0.229900 11.00000 -1.50000 AFIX 0 C9 1 0.230492 0.348697 0.400319 11.00000 0.01766 0.02389 = 0.01912 -0.00047 -0.00156 -0.00090 C10 1 0.095523 0.353635 0.473526 11.00000 0.01873 0.03126 = 0.02296 -0.00141 -0.00034 0.00114 AFIX 43 H10 2 0.014246 0.373565 0.445965 11.00000 -1.20000 AFIX 0 C11 1 0.067868 0.328713 0.598101 11.00000 0.02115 0.04453 = 0.02239 0.00065 0.00378 -0.00145 AFIX 23 H11A 2 -0.026796 0.339950 0.646568 11.00000 -1.20000 H11B 2 0.173621 0.328956 0.664099 11.00000 -1.20000 AFIX 0 C12 1 0.023080 0.286144 0.555842 11.00000 0.02344 0.04311 = 0.03066 0.00705 0.00327 -0.00718 AFIX 23 H12A 2 0.041601 0.269290 0.639666 11.00000 -1.20000 H12B 2 -0.100540 0.284729 0.521220 11.00000 -1.20000 AFIX 0 C13 1 0.129305 0.270029 0.443256 11.00000 0.02425 0.03134 = 0.02924 0.00189 -0.00047 -0.00863 AFIX 23 H13A 2 0.084261 0.281257 0.352029 11.00000 -1.20000 H13B 2 0.112913 0.241310 0.437537 11.00000 -1.20000 AFIX 0 C14 1 0.480771 0.440649 0.472928 11.00000 0.02085 0.01959 = 0.02654 -0.00290 0.00081 0.00002 C15 1 0.516812 0.461987 0.356731 11.00000 0.02629 0.02508 = 0.02986 -0.00125 0.00540 -0.00330 AFIX 43 H15 2 0.629573 0.461939 0.327646 11.00000 -1.20000 AFIX 0 C16 1 0.386334 0.483406 0.283441 11.00000 0.03886 0.02528 = 0.02897 0.00273 0.00189 -0.00242 AFIX 43 H16 2 0.411284 0.498452 0.204947 11.00000 -1.20000 AFIX 0 C17 1 0.219387 0.483239 0.322921 11.00000 0.03085 0.02131 = 0.03375 -0.00400 -0.00619 0.00074 C18 1 0.186191 0.461638 0.440048 11.00000 0.02233 0.02558 = 0.03931 -0.00296 0.00196 0.00054 AFIX 43 H18 2 0.073058 0.461286 0.468361 11.00000 -1.20000 AFIX 0 C19 1 0.315609 0.440677 0.515800 11.00000 0.02504 0.02457 = 0.02963 0.00033 0.00527 -0.00014 AFIX 43 H19 2 0.291900 0.426421 0.596421 11.00000 -1.20000 AFIX 0 C20 1 0.078277 0.506443 0.242733 11.00000 0.04082 0.02969 = 0.04493 -0.00139 -0.01422 0.00436 AFIX 137 H20A 2 -0.033843 0.497101 0.266529 11.00000 -1.50000 H20B 2 0.085457 0.503117 0.142373 11.00000 -1.50000 H20C 2 0.091370 0.534216 0.267104 11.00000 -1.50000 AFIX 0 C21 1 -0.047676 0.392465 -0.009647 11.00000 0.02103 0.03760 = 0.02151 0.00506 -0.00365 0.00102 AFIX 13 H21 2 -0.025478 0.404243 -0.101241 11.00000 -1.20000 AFIX 0 C22 1 -0.180936 0.417836 0.052238 11.00000 0.02300 0.04612 = 0.03767 0.00101 -0.00323 0.00624 AFIX 137 H22A 2 -0.287453 0.418113 -0.010980 11.00000 -1.50000 H22B 2 -0.136755 0.444596 0.064714 11.00000 -1.50000 H22C 2 -0.204491 0.407149 0.142867 11.00000 -1.50000 AFIX 0 C23 1 -0.113517 0.350998 -0.037893 11.00000 0.03420 0.04230 = 0.03410 -0.00029 -0.00746 -0.00381 AFIX 137 H23A 2 -0.021871 0.334990 -0.071325 11.00000 -1.50000 H23B 2 -0.212546 0.351618 -0.108986 11.00000 -1.50000 H23C 2 -0.148535 0.339683 0.048443 11.00000 -1.50000 AFIX 0 C24 1 0.283817 0.401851 0.029448 11.00000 0.02047 0.03130 = 0.02285 0.00231 0.00196 -0.00082 AFIX 13 H24 2 0.366572 0.408419 0.112260 11.00000 -1.20000 AFIX 0 C25 1 0.272638 0.437445 -0.066157 11.00000 0.03249 0.04705 = 0.03762 0.01717 0.00444 0.00027 AFIX 137 H25A 2 0.204204 0.430908 -0.154036 11.00000 -1.50000 H25B 2 0.388754 0.445247 -0.085387 11.00000 -1.50000 H25C 2 0.217760 0.459100 -0.020607 11.00000 -1.50000 AFIX 0 C26 1 0.354015 0.365932 -0.039479 11.00000 0.03158 0.04244 = 0.03856 -0.00949 0.00994 -0.00036 AFIX 137 H26A 2 0.365113 0.344265 0.027556 11.00000 -1.50000 H26B 2 0.467193 0.372018 -0.069780 11.00000 -1.50000 H26C 2 0.274921 0.358395 -0.120576 11.00000 -1.50000 AFIX 0 HKLF 4 REM cb715-1.res in P2(1)/c REM wR2 = 0.0816, GooF = S = 1.022, Restrained GooF = 1.022 for all data REM R1 = 0.0310 for 4698 Fo > 4sig(Fo) and 0.0330 for all 5004 data REM 314 parameters refined using 0 restraints END WGHT 0.0405 0.9103 REM Highest difference peak 0.303, deepest hole -0.348, 1-sigma level 0.036 Q1 1 0.5518 0.4277 0.5142 11.00000 0.05 0.30 Q2 1 0.4214 0.3302 0.5188 11.00000 0.05 0.27 Q3 1 0.4468 0.3210 0.4017 11.00000 0.05 0.27 Q4 1 0.3087 0.3355 0.4337 11.00000 0.05 0.27 Q5 1 0.3455 0.3010 0.4659 11.00000 0.05 0.26 Q6 1 0.4794 0.2711 0.3191 11.00000 0.05 0.24 Q7 1 0.2283 0.2724 0.4576 11.00000 0.05 0.23 Q8 1 0.2076 0.4724 0.3824 11.00000 0.05 0.21 Q9 1 0.3721 0.2682 0.4200 11.00000 0.05 0.21 Q10 1 0.1445 0.3420 0.4180 11.00000 0.05 0.21 ; _shelx_res_checksum 79910 _olex2_date_sample_data_collection 2021-05-06 _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 - Detector area scaling - B-factor correction ; _oxdiff_exptl_absorpt_empirical_full_max 1.338 _oxdiff_exptl_absorpt_empirical_full_min 0.764 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -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 S1 S 0.64292(3) 0.41191(2) 0.56375(3) 0.02248(9) Uani 1 1 d . . . . . O1 O 0.40189(14) 0.22251(3) 0.33081(10) 0.0369(2) Uani 1 1 d . . . . . O2 O 0.80310(11) 0.42348(3) 0.51493(10) 0.0311(2) Uani 1 1 d . . . . . O3 O 0.62115(12) 0.41331(3) 0.70990(9) 0.0298(2) Uani 1 1 d . . . . . N1 N 0.61209(12) 0.36658(3) 0.51642(10) 0.0220(2) Uani 1 1 d . . . . . N2 N 0.25251(12) 0.36711(3) 0.27102(10) 0.0209(2) Uani 1 1 d . . . . . N3 N 0.10777(12) 0.37393(3) 0.20096(10) 0.0229(2) Uani 1 1 d . . . . . N4 N 0.11660(12) 0.39308(3) 0.08175(10) 0.0245(2) Uani 1 1 d . . . . . C1 C 0.37995(14) 0.32199(3) 0.45403(11) 0.0192(2) Uani 1 1 d . . . . . C2 C 0.32275(15) 0.27868(3) 0.46791(12) 0.0222(2) Uani 1 1 d . . . . . H2 H 0.366043 0.269120 0.563177 0.027 Uiso 1 1 calc R U . . . C3 C 0.41999(16) 0.25700(4) 0.36055(12) 0.0249(2) Uani 1 1 d . . . . . C4 C 0.54437(15) 0.28396(4) 0.30413(12) 0.0234(2) Uani 1 1 d . . . . . C5 C 0.52047(14) 0.31952(3) 0.35643(11) 0.0200(2) Uani 1 1 d . . . . . C6 C 0.63016(14) 0.35530(3) 0.36924(12) 0.0223(2) Uani 1 1 d . . . . . H6A H 0.751255 0.349366 0.354823 0.027 Uiso 1 1 calc R U . . . H6B H 0.585756 0.375933 0.302909 0.027 Uiso 1 1 calc R U . . . C7 C 0.48665(14) 0.34103(3) 0.58084(12) 0.0218(2) Uani 1 1 d . . . . . H7A H 0.412081 0.356668 0.637053 0.026 Uiso 1 1 calc R U . . . H7B H 0.547004 0.320865 0.641302 0.026 Uiso 1 1 calc R U . . . C8 C 0.67894(17) 0.27055(4) 0.21485(15) 0.0332(3) Uani 1 1 d . . . . . H8A H 0.632786 0.271602 0.116429 0.050 Uiso 1 1 calc R U . . . H8B H 0.712387 0.243589 0.239653 0.050 Uiso 1 1 calc R U . . . H8C H 0.779896 0.287651 0.229900 0.050 Uiso 1 1 calc R U . . . C9 C 0.23049(14) 0.34870(3) 0.40032(11) 0.0205(2) Uani 1 1 d . . . . . C10 C 0.09552(15) 0.35363(4) 0.47353(12) 0.0245(2) Uani 1 1 d . . . . . H10 H 0.014246 0.373565 0.445965 0.029 Uiso 1 1 calc R U . . . C11 C 0.06787(16) 0.32871(4) 0.59810(13) 0.0293(3) Uani 1 1 d . . . . . H11A H -0.026796 0.339950 0.646568 0.035 Uiso 1 1 calc R U . . . H11B H 0.173621 0.328956 0.664099 0.035 Uiso 1 1 calc R U . . . C12 C 0.02308(17) 0.28614(4) 0.55584(14) 0.0324(3) Uani 1 1 d . . . . . H12A H 0.041601 0.269290 0.639666 0.039 Uiso 1 1 calc R U . . . H12B H -0.100540 0.284729 0.521220 0.039 Uiso 1 1 calc R U . . . C13 C 0.12930(16) 0.27003(4) 0.44326(13) 0.0285(3) Uani 1 1 d . . . . . H13A H 0.084261 0.281257 0.352029 0.034 Uiso 1 1 calc R U . . . H13B H 0.112913 0.241310 0.437537 0.034 Uiso 1 1 calc R U . . . C14 C 0.48077(15) 0.44065(3) 0.47293(12) 0.0224(2) Uani 1 1 d . . . . . C15 C 0.51681(16) 0.46199(4) 0.35673(13) 0.0269(3) Uani 1 1 d . . . . . H15 H 0.629573 0.461939 0.327646 0.032 Uiso 1 1 calc R U . . . C16 C 0.38633(18) 0.48341(4) 0.28344(14) 0.0311(3) Uani 1 1 d . . . . . H16 H 0.411284 0.498452 0.204947 0.037 Uiso 1 1 calc R U . . . C17 C 0.21939(17) 0.48324(4) 0.32292(14) 0.0293(3) Uani 1 1 d . . . . . C18 C 0.18619(16) 0.46164(4) 0.44005(14) 0.0292(3) Uani 1 1 d . . . . . H18 H 0.073058 0.461286 0.468361 0.035 Uiso 1 1 calc R U . . . C19 C 0.31561(16) 0.44068(4) 0.51580(13) 0.0262(3) Uani 1 1 d . . . . . H19 H 0.291900 0.426421 0.596421 0.031 Uiso 1 1 calc R U . . . C20 C 0.0783(2) 0.50644(4) 0.24273(16) 0.0397(3) Uani 1 1 d . . . . . H20A H -0.033843 0.497101 0.266529 0.060 Uiso 1 1 calc R U . . . H20B H 0.085457 0.503117 0.142373 0.060 Uiso 1 1 calc R U . . . H20C H 0.091370 0.534216 0.267104 0.060 Uiso 1 1 calc R U . . . C21 C -0.04768(15) 0.39247(4) -0.00965(12) 0.0271(3) Uani 1 1 d . . . . . H21 H -0.025478 0.404243 -0.101241 0.033 Uiso 1 1 calc R U . . . C22 C -0.18094(17) 0.41784(5) 0.05224(15) 0.0360(3) Uani 1 1 d . . . . . H22A H -0.287453 0.418113 -0.010980 0.054 Uiso 1 1 calc R U . . . H22B H -0.136755 0.444596 0.064714 0.054 Uiso 1 1 calc R U . . . H22C H -0.204491 0.407149 0.142867 0.054 Uiso 1 1 calc R U . . . C23 C -0.11352(19) 0.35100(4) -0.03789(15) 0.0376(3) Uani 1 1 d . . . . . H23A H -0.021871 0.334990 -0.071325 0.056 Uiso 1 1 calc R U . . . H23B H -0.212546 0.351618 -0.108986 0.056 Uiso 1 1 calc R U . . . H23C H -0.148535 0.339683 0.048443 0.056 Uiso 1 1 calc R U . . . C24 C 0.28382(15) 0.40185(4) 0.02945(12) 0.0249(2) Uani 1 1 d . . . . . H24 H 0.366572 0.408419 0.112260 0.030 Uiso 1 1 calc R U . . . C25 C 0.27264(19) 0.43745(5) -0.06616(15) 0.0390(3) Uani 1 1 d . . . . . H25A H 0.204204 0.430908 -0.154036 0.058 Uiso 1 1 calc R U . . . H25B H 0.388754 0.445247 -0.085387 0.058 Uiso 1 1 calc R U . . . H25C H 0.217760 0.459100 -0.020607 0.058 Uiso 1 1 calc R U . . . C26 C 0.35402(18) 0.36593(5) -0.03948(15) 0.0371(3) Uani 1 1 d . . . . . H26A H 0.365113 0.344265 0.027556 0.056 Uiso 1 1 calc R U . . . H26B H 0.467193 0.372018 -0.069780 0.056 Uiso 1 1 calc R U . . . H26C H 0.274921 0.358395 -0.120576 0.056 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 0.01824(15) 0.02110(15) 0.02738(16) -0.00326(10) -0.00123(10) -0.00082(10) O1 0.0508(6) 0.0244(5) 0.0363(5) -0.0055(4) 0.0089(4) -0.0068(4) O2 0.0187(4) 0.0271(4) 0.0473(5) -0.0052(4) 0.0025(4) -0.0033(3) O3 0.0332(5) 0.0285(5) 0.0262(4) -0.0045(3) -0.0046(4) 0.0006(4) N1 0.0199(5) 0.0208(5) 0.0250(5) -0.0024(4) 0.0012(4) -0.0017(4) N2 0.0179(4) 0.0242(5) 0.0200(4) 0.0008(4) -0.0005(3) 0.0014(4) N3 0.0202(5) 0.0284(5) 0.0196(5) 0.0017(4) -0.0003(4) 0.0022(4) N4 0.0185(5) 0.0343(6) 0.0203(5) 0.0053(4) -0.0002(4) 0.0014(4) C1 0.0170(5) 0.0223(5) 0.0178(5) 0.0007(4) -0.0006(4) -0.0012(4) C2 0.0224(6) 0.0234(6) 0.0203(5) 0.0018(4) -0.0013(4) -0.0027(4) C3 0.0262(6) 0.0251(6) 0.0223(6) -0.0008(4) -0.0026(4) -0.0011(5) C4 0.0200(5) 0.0262(6) 0.0235(5) -0.0031(4) -0.0011(4) 0.0001(4) C5 0.0155(5) 0.0244(6) 0.0193(5) 0.0010(4) -0.0018(4) 0.0003(4) C6 0.0172(5) 0.0244(6) 0.0254(6) -0.0022(4) 0.0027(4) -0.0011(4) C7 0.0204(5) 0.0237(6) 0.0205(5) 0.0013(4) -0.0019(4) -0.0019(4) C8 0.0272(6) 0.0342(7) 0.0391(7) -0.0119(6) 0.0078(5) -0.0018(5) C9 0.0177(5) 0.0239(5) 0.0191(5) -0.0005(4) -0.0016(4) -0.0009(4) C10 0.0187(5) 0.0313(6) 0.0230(6) -0.0014(5) -0.0003(4) 0.0011(5) C11 0.0212(6) 0.0445(8) 0.0224(6) 0.0006(5) 0.0038(4) -0.0014(5) C12 0.0234(6) 0.0431(8) 0.0307(6) 0.0071(6) 0.0033(5) -0.0072(5) C13 0.0243(6) 0.0313(6) 0.0292(6) 0.0019(5) -0.0005(5) -0.0086(5) C14 0.0209(5) 0.0196(5) 0.0265(6) -0.0029(4) 0.0008(4) 0.0000(4) C15 0.0263(6) 0.0251(6) 0.0299(6) -0.0012(5) 0.0054(5) -0.0033(5) C16 0.0389(7) 0.0253(6) 0.0290(6) 0.0027(5) 0.0019(5) -0.0024(5) C17 0.0309(6) 0.0213(6) 0.0338(6) -0.0040(5) -0.0062(5) 0.0007(5) C18 0.0223(6) 0.0256(6) 0.0393(7) -0.0030(5) 0.0020(5) 0.0005(5) C19 0.0250(6) 0.0246(6) 0.0296(6) 0.0003(5) 0.0053(5) -0.0001(5) C20 0.0408(8) 0.0297(7) 0.0449(8) -0.0014(6) -0.0142(6) 0.0044(6) C21 0.0210(6) 0.0376(7) 0.0215(5) 0.0051(5) -0.0037(4) 0.0010(5) C22 0.0230(6) 0.0461(8) 0.0377(7) 0.0010(6) -0.0032(5) 0.0062(6) C23 0.0342(7) 0.0423(8) 0.0341(7) -0.0003(6) -0.0075(6) -0.0038(6) C24 0.0205(6) 0.0313(6) 0.0228(5) 0.0023(5) 0.0020(4) -0.0008(5) C25 0.0325(7) 0.0471(8) 0.0376(7) 0.0172(6) 0.0044(6) 0.0003(6) C26 0.0316(7) 0.0424(8) 0.0386(7) -0.0095(6) 0.0099(6) -0.0004(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 0 0.0153 0 -1 0 0.0191 -1 0 0 0.0896 1 0 0 0.0877 0 0 -1 0.1247 0 0 1 0.1150 -2 1 2 0.1224 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 O2 S1 O3 120.32(6) . . ? O2 S1 N1 106.25(5) . . ? O2 S1 C14 106.87(6) . . ? O3 S1 N1 106.14(5) . . ? O3 S1 C14 108.55(6) . . ? N1 S1 C14 108.21(5) . . ? C6 N1 S1 119.21(8) . . ? C6 N1 C7 111.89(9) . . ? C7 N1 S1 121.71(8) . . ? N3 N2 C9 111.42(9) . . ? N2 N3 N4 115.22(10) . . ? N3 N4 C21 112.93(9) . . ? N3 N4 C24 121.24(9) . . ? C24 N4 C21 122.88(9) . . ? C5 C1 C2 103.41(9) . . ? C5 C1 C7 98.42(8) . . ? C5 C1 C9 113.48(9) . . ? C7 C1 C2 117.88(9) . . ? C9 C1 C2 112.37(9) . . ? C9 C1 C7 110.34(9) . . ? C1 C2 H2 108.4 . . ? C3 C2 C1 103.64(9) . . ? C3 C2 H2 108.4 . . ? C3 C2 C13 110.42(10) . . ? C13 C2 C1 117.18(10) . . ? C13 C2 H2 108.4 . . ? O1 C3 C2 124.92(11) . . ? O1 C3 C4 125.50(12) . . ? C4 C3 C2 109.52(10) . . ? C3 C4 C8 123.03(11) . . ? C5 C4 C3 107.81(10) . . ? C5 C4 C8 128.96(11) . . ? C4 C5 C1 114.93(10) . . ? C4 C5 C6 132.56(11) . . ? C6 C5 C1 110.38(9) . . ? N1 C6 C5 100.52(9) . . ? N1 C6 H6A 111.7 . . ? N1 C6 H6B 111.7 . . ? C5 C6 H6A 111.7 . . ? C5 C6 H6B 111.7 . . ? H6A C6 H6B 109.4 . . ? N1 C7 C1 103.95(9) . . ? N1 C7 H7A 111.0 . . ? N1 C7 H7B 111.0 . . ? C1 C7 H7A 111.0 . . ? C1 C7 H7B 111.0 . . ? H7A C7 H7B 109.0 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 C1 113.90(9) . . ? C10 C9 N2 125.28(11) . . ? C10 C9 C1 120.81(10) . . ? C9 C10 H10 118.9 . . ? C9 C10 C11 122.22(11) . . ? C11 C10 H10 118.9 . . ? C10 C11 H11A 109.3 . . ? C10 C11 H11B 109.3 . . ? C10 C11 C12 111.75(10) . . ? H11A C11 H11B 107.9 . . ? C12 C11 H11A 109.3 . . ? C12 C11 H11B 109.3 . . ? C11 C12 H12A 108.8 . . ? C11 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? C13 C12 C11 113.67(10) . . ? C13 C12 H12A 108.8 . . ? C13 C12 H12B 108.8 . . ? C2 C13 H13A 108.6 . . ? C2 C13 H13B 108.6 . . ? C12 C13 C2 114.57(10) . . ? C12 C13 H13A 108.6 . . ? C12 C13 H13B 108.6 . . ? H13A C13 H13B 107.6 . . ? C15 C14 S1 119.92(9) . . ? C15 C14 C19 120.48(11) . . ? C19 C14 S1 119.56(9) . . ? C14 C15 H15 120.4 . . ? C14 C15 C16 119.28(12) . . ? C16 C15 H15 120.4 . . ? C15 C16 H16 119.4 . . ? C15 C16 C17 121.19(12) . . ? C17 C16 H16 119.4 . . ? C16 C17 C20 120.94(13) . . ? C18 C17 C16 118.54(12) . . ? C18 C17 C20 120.52(13) . . ? C17 C18 H18 119.5 . . ? C19 C18 C17 120.99(12) . . ? C19 C18 H18 119.5 . . ? C14 C19 H19 120.2 . . ? C18 C19 C14 119.51(12) . . ? C18 C19 H19 120.2 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N4 C21 H21 107.6 . . ? N4 C21 C22 110.17(10) . . ? N4 C21 C23 112.10(11) . . ? C22 C21 H21 107.6 . . ? C22 C21 C23 111.61(11) . . ? C23 C21 H21 107.6 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22B 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23B 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N4 C24 H24 107.2 . . ? N4 C24 C25 111.67(10) . . ? N4 C24 C26 110.75(11) . . ? C25 C24 H24 107.2 . . ? C25 C24 C26 112.42(11) . . ? C26 C24 H24 107.2 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25B 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26B 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 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 O2 1.4345(9) . ? S1 O3 1.4349(9) . ? S1 N1 1.6249(10) . ? S1 C14 1.7630(12) . ? O1 C3 1.2170(16) . ? N1 C6 1.4887(15) . ? N1 C7 1.4923(15) . ? N2 N3 1.2778(14) . ? N2 C9 1.4204(15) . ? N3 N4 1.3286(14) . ? N4 C21 1.4808(14) . ? N4 C24 1.4761(15) . ? C1 C2 1.5548(15) . ? C1 C5 1.5164(15) . ? C1 C7 1.5502(15) . ? C1 C9 1.5294(15) . ? C2 H2 1.0000 . ? C2 C3 1.5329(17) . ? C2 C13 1.5336(16) . ? C3 C4 1.4802(17) . ? C4 C5 1.3349(17) . ? C4 C8 1.4943(17) . ? C5 C6 1.4902(16) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.3356(17) . ? C10 H10 0.9500 . ? C10 C11 1.5038(17) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C11 C12 1.5405(19) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C12 C13 1.5314(19) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.3873(17) . ? C14 C19 1.3925(17) . ? C15 H15 0.9500 . ? C15 C16 1.3879(19) . ? C16 H16 0.9500 . ? C16 C17 1.394(2) . ? C17 C18 1.3933(19) . ? C17 C20 1.5056(18) . ? C18 H18 0.9500 . ? C18 C19 1.3846(18) . ? C19 H19 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21 1.0000 . ? C21 C22 1.5205(19) . ? C21 C23 1.5218(19) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24 1.0000 . ? C24 C25 1.5220(18) . ? C24 C26 1.5226(18) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? 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 N1 C6 C5 -155.87(8) . . . . ? S1 N1 C7 C1 131.44(8) . . . . ? S1 C14 C15 C16 177.80(9) . . . . ? S1 C14 C19 C18 -176.65(10) . . . . ? O1 C3 C4 C5 177.28(12) . . . . ? O1 C3 C4 C8 -7.47(19) . . . . ? O2 S1 N1 C6 -49.34(9) . . . . ? O2 S1 N1 C7 162.71(8) . . . . ? O2 S1 C14 C15 13.22(11) . . . . ? O2 S1 C14 C19 -168.95(9) . . . . ? O3 S1 N1 C6 -178.53(8) . . . . ? O3 S1 N1 C7 33.52(10) . . . . ? O3 S1 C14 C15 144.39(10) . . . . ? O3 S1 C14 C19 -37.78(11) . . . . ? N1 S1 C14 C15 -100.84(10) . . . . ? N1 S1 C14 C19 76.99(10) . . . . ? N2 N3 N4 C21 167.11(10) . . . . ? N2 N3 N4 C24 6.02(16) . . . . ? N2 C9 C10 C11 170.56(11) . . . . ? N3 N2 C9 C1 150.85(10) . . . . ? N3 N2 C9 C10 -30.05(16) . . . . ? N3 N4 C21 C22 70.47(14) . . . . ? N3 N4 C21 C23 -54.46(14) . . . . ? N3 N4 C24 C25 -154.83(12) . . . . ? N3 N4 C24 C26 79.05(14) . . . . ? C1 C2 C3 O1 -174.52(12) . . . . ? C1 C2 C3 C4 8.14(12) . . . . ? C1 C2 C13 C12 -68.96(14) . . . . ? C1 C5 C6 N1 28.34(11) . . . . ? C1 C9 C10 C11 -10.39(18) . . . . ? C2 C1 C5 C4 5.00(12) . . . . ? C2 C1 C5 C6 -160.57(9) . . . . ? C2 C1 C7 N1 143.04(10) . . . . ? C2 C1 C9 N2 -118.50(10) . . . . ? C2 C1 C9 C10 62.35(14) . . . . ? C2 C3 C4 C5 -5.39(13) . . . . ? C2 C3 C4 C8 169.86(11) . . . . ? C3 C2 C13 C12 172.75(10) . . . . ? C3 C4 C5 C1 0.10(13) . . . . ? C3 C4 C5 C6 161.61(12) . . . . ? C4 C5 C6 N1 -133.79(13) . . . . ? C5 C1 C2 C3 -7.54(11) . . . . ? C5 C1 C2 C13 -129.42(10) . . . . ? C5 C1 C7 N1 32.95(10) . . . . ? C5 C1 C9 N2 -1.62(13) . . . . ? C5 C1 C9 C10 179.23(11) . . . . ? C6 N1 C7 C1 -18.62(12) . . . . ? C7 N1 C6 C5 -4.98(11) . . . . ? C7 C1 C2 C3 -114.78(10) . . . . ? C7 C1 C2 C13 123.33(11) . . . . ? C7 C1 C5 C4 126.41(10) . . . . ? C7 C1 C5 C6 -39.16(11) . . . . ? C7 C1 C9 N2 107.73(10) . . . . ? C7 C1 C9 C10 -71.42(14) . . . . ? C8 C4 C5 C1 -174.78(12) . . . . ? C8 C4 C5 C6 -13.3(2) . . . . ? C9 N2 N3 N4 176.49(10) . . . . ? C9 C1 C2 C3 115.21(10) . . . . ? C9 C1 C2 C13 -6.68(14) . . . . ? C9 C1 C5 C4 -117.01(11) . . . . ? C9 C1 C5 C6 77.42(11) . . . . ? C9 C1 C7 N1 -86.03(10) . . . . ? C9 C10 C11 C12 -68.66(15) . . . . ? C10 C11 C12 C13 41.11(15) . . . . ? C11 C12 C13 C2 45.53(15) . . . . ? C13 C2 C3 O1 -48.22(16) . . . . ? C13 C2 C3 C4 134.43(10) . . . . ? C14 S1 N1 C6 65.13(9) . . . . ? C14 S1 N1 C7 -82.82(9) . . . . ? C14 C15 C16 C17 -1.24(19) . . . . ? C15 C14 C19 C18 1.17(18) . . . . ? C15 C16 C17 C18 1.31(19) . . . . ? C15 C16 C17 C20 -179.82(12) . . . . ? C16 C17 C18 C19 -0.13(19) . . . . ? C17 C18 C19 C14 -1.09(19) . . . . ? C19 C14 C15 C16 -0.02(18) . . . . ? C20 C17 C18 C19 -179.00(12) . . . . ? C21 N4 C24 C25 45.98(16) . . . . ? C21 N4 C24 C26 -80.13(14) . . . . ? C24 N4 C21 C22 -128.79(12) . . . . ? C24 N4 C21 C23 106.28(13) . . . . ? loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -0.0001 1.0004 -0.0000 0.0007 0.0448 -0.0055 0.0001 -1.0004 0.0000 -0.0007 -0.0448 0.0055 -1.0000 0.0003 -0.0003 0.1974 -0.0006 0.0199 1.0000 -0.0003 0.0003 -0.1974 0.0006 -0.0199 -0.0009 0.0014 -0.9997 0.0003 0.0197 0.1596 0.0009 -0.0014 0.9997 -0.0003 -0.0197 -0.1596 -1.9985 0.9981 1.9988 0.3949 0.0041 -0.2848