#------------------------------------------------------------------------------ #$Date: 2024-01-06 10:01:35 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288801 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247719.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_7247719 loop_ _publ_author_name 'Madhesiya, Avinash' 'Dash, Sibananda G.' 'Gupta, Princi' 'Akhir, Abdul' 'Saxena, Deepanshi' 'Maitra, Rahul' 'Chopra, Sidharth' 'Thakur, Tejender S.' _publ_section_title ; Development of new multicomponent crystals of the antifungal drug tioconazole and the assessment of their biopharmaceutical attributes ; _journal_issue 48 _journal_name_full CrystEngComm _journal_page_first 6758 _journal_page_last 6776 _journal_paper_doi 10.1039/D3CE00948C _journal_volume 25 _journal_year 2023 _chemical_formula_moiety 'C16 H14 Cl3 N2 O S, C4 H5 O6, 3(H2 O), 0.42(O)' _chemical_formula_sum 'C20 H25 Cl3 N2 O10.42 S' _chemical_formula_weight 598.57 _chemical_name_common 'Tioconazole-L-tartrate 1:1 salt hydrate' _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 mixed _audit_creation_method SHELXL-2019/2 _audit_update_record ; 2023-09-21 deposited with the CCDC. 2023-11-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.60280(10) _cell_length_b 9.94440(10) _cell_length_c 35.6016(4) _cell_measurement_reflns_used 54997 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 76.6930 _cell_measurement_theta_min 2.4770 _cell_volume 2691.67(5) _computing_cell_refinement 'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)' _computing_data_collection 'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)' _computing_data_reduction 'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)' _computing_structure_refinement 'SHELXL-2019/2 (Sheldrick, 2019)' _computing_structure_solution 'SHELXL-2018/2 (Sheldrick, 2015)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.987 _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 -19.00 22.00 0.50 0.05 -- 14.00 100.00-175.98 82 2 \w 2.00 43.00 0.50 0.05 -- 30.00 88.00 -80.38 82 3 \w -20.00 7.00 0.50 0.05 -- 14.00 103.00 -20.34 54 4 \w 0.00 34.00 0.50 0.05 -- 30.00 93.00 115.73 68 5 \w 13.00 42.00 0.50 0.05 -- 42.00 91.00 12.02 58 6 \w 14.00 43.00 0.50 0.05 -- 42.00 88.00 87.55 58 7 \w 25.00 119.00 0.50 0.05 -- 47.33 77.00 120.00 188 8 \w 35.00 122.00 0.50 0.05 -- 47.33 19.00 150.00 174 9 \w 32.00 126.00 0.50 0.05 -- 54.00 75.00 33.66 188 10 \w 44.00 139.00 0.50 0.05 -- 66.00 75.00 -25.96 190 11 \w 44.00 139.00 0.50 0.05 -- 66.00 76.00 -69.39 190 12 \w 25.00 119.00 0.50 0.05 -- 47.33 77.00-150.00 188 13 \w 33.00 126.00 0.50 0.05 -- 54.00 74.00-127.64 186 14 \w 38.00 131.00 0.50 0.05 -- 58.00 71.00 -99.18 186 15 \w 44.00 139.00 0.50 0.05 -- 66.00 76.00 -69.39 190 16 \w 120.00 174.00 0.50 0.22 -- 109.61 125.00 -30.00 108 17 \w 107.00 178.00 0.50 0.22 -- 109.61 101.00 4.00 142 18 \w 38.00 63.00 0.50 0.22 -- 109.61 -57.00 30.00 50 19 \w 38.00 63.00 0.50 0.22 -- 109.61 -57.00 60.00 50 20 \w 38.00 63.00 0.50 0.22 -- 109.61 -57.00 120.00 50 21 \w 40.00 106.00 0.50 0.22 -- 109.61-125.00 120.00 132 22 \w 41.00 109.00 0.50 0.22 -- 109.61-125.00 150.00 136 23 \w 77.00 108.00 0.50 0.22 -- 109.61-125.00 -30.00 62 24 \w 81.00 106.00 0.50 0.22 -- 109.61 -99.00 -30.00 50 25 \w 40.00 68.00 0.50 0.22 -- 109.61-125.00 -30.00 56 26 \w 39.00 106.00 0.50 0.22 -- 109.61-101.00 -99.00 134 27 \w 71.00 105.00 0.50 0.22 -- 109.61 -99.00-150.00 68 28 \w 40.00 66.00 0.50 0.22 -- 109.61 -99.00-150.00 52 29 \w 39.00 74.00 0.50 0.22 -- 109.61 -99.00 -30.00 70 30 \w 48.00 89.00 0.50 0.22 -- 109.61 -99.00 -60.00 82 31 \w 39.00 106.00 0.50 0.22 -- 109.61 -99.00 150.00 134 32 \w 77.00 104.00 0.50 0.22 -- 109.61 -99.00 30.00 54 33 \w 44.00 73.00 0.50 0.22 -- 109.61 -99.00 30.00 58 34 \w 4.00 81.00 0.50 0.05 -- 47.33-101.00 -99.00 154 35 \w 34.00 93.00 0.50 0.05 -- 47.33-125.00-180.00 118 36 \w 34.00 93.00 0.50 0.05 -- 47.33-125.00 0.00 118 37 \w -119.00 -25.00 0.50 0.05 -- -47.33 -77.00 120.00 188 38 \w -119.00 -25.00 0.50 0.05 -- -47.33 -77.00 -60.00 188 39 \w -119.00 -25.00 0.50 0.05 -- -47.33 -77.00 -90.00 188 40 \w -119.00 -25.00 0.50 0.05 -- -47.33 -77.00-180.00 188 41 \w -162.00 -85.00 0.50 0.22 -- -91.75-101.00 -99.00 154 42 \w -92.00 -59.00 0.50 0.22 -- -82.00 -77.00-110.52 66 43 \w -126.00 -31.00 0.50 0.05 -- -54.00 -77.00 -99.09 190 44 \w -156.00-127.00 0.50 0.22 -- -91.75 -77.00-162.74 58 45 \w -110.00 -69.00 0.50 0.22 -- -91.75 -77.00-162.74 82 46 \w -89.00 -63.00 0.50 0.22 -- -86.00 -77.00 -55.63 52 47 \w -110.00 -69.00 0.50 0.22 -- -91.75 -77.00 -30.00 82 48 \w -151.00 -69.00 0.50 0.22 -- -91.75 -77.00 -65.36 164 49 \w -162.00-136.00 0.50 0.22 -- -91.75 -77.00 -30.00 52 50 \w -114.00 -69.00 0.50 0.22 -- -91.75 -77.00 90.00 90 51 \w -139.00 -43.00 0.50 0.05 -- -66.00 -77.00 176.54 192 52 \w -147.00-121.00 0.50 0.22 -- -91.75 -77.00 90.00 52 53 \w -161.00 -94.00 0.50 0.22 -- -91.75 -77.00 30.00 134 54 \w -77.00 -51.00 0.50 0.05 -- -74.00 -76.00 69.91 52 55 \w -77.00 -51.00 0.50 0.05 -- -74.00 -76.00 -20.06 52 56 \w -161.00 -69.00 0.50 0.22 -- -91.75 -77.00-180.00 184 57 \w -139.00 -43.00 0.50 0.05 -- -66.00 -76.00-123.20 192 58 \w -143.00 -47.00 0.50 0.05 -- -70.00 -77.00 0.34 192 59 \w -144.00 -67.00 0.50 0.22 -- -90.00 -76.00 61.89 154 60 \w -77.00 -51.00 0.50 0.05 -- -74.00 -76.00 145.45 52 61 \w -88.00 -63.00 0.50 0.22 -- -86.00 -76.00 136.35 50 62 \w -154.00-104.00 0.50 0.22 -- -86.00 -76.00 136.35 100 63 \w -98.00 -69.00 0.50 0.22 -- -91.75 -76.00 -0.79 58 64 \w -94.00 -69.00 0.50 0.22 -- -91.75 -76.00 15.30 50 65 \w -154.00-110.00 0.50 0.22 -- -91.75 -76.00 15.30 88 66 \w -163.00-128.00 0.50 0.22 -- -91.75 -76.00 -0.79 70 67 \w -78.00 -52.00 0.50 0.05 -- -74.00 -74.00 -79.53 52 68 \w -86.00 -60.00 0.50 0.22 -- -82.00 -75.00-130.18 52 69 \w -85.00 -52.00 0.50 0.05 -- -74.00 -75.00-150.35 66 70 \w -143.00 -70.00 0.50 0.22 -- -91.75 -75.00-147.78 146 71 \w -82.00 -56.00 0.50 0.05 -- -78.00 -74.00 106.21 52 72 \w -79.00 -53.00 0.50 0.05 -- -74.00 -74.00 130.10 52 73 \w -146.00 -70.00 0.50 0.22 -- -91.75 -74.00 160.43 152 74 \w -163.00-113.00 0.50 0.22 -- -91.75 -74.00 128.67 100 75 \w -101.00 -71.00 0.50 0.22 -- -91.75 -74.00 128.67 60 76 \w -100.00 -64.00 0.50 0.22 -- -86.00 -74.00 49.13 72 77 \w -148.00-108.00 0.50 0.22 -- -86.00 -74.00 49.13 80 78 \w -135.00 -40.00 0.50 0.05 -- -62.00 -74.00 32.89 190 79 \w -86.00 -60.00 0.50 0.22 -- -82.00 -74.00 -38.52 52 80 \w -88.00 -62.00 0.50 0.22 -- -82.00 -73.00 -94.99 52 81 \w -154.00-116.00 0.50 0.22 -- -82.00 -73.00 -94.99 76 82 \w -151.00-126.00 0.50 0.22 -- -91.75 -71.00-138.10 50 83 \w -161.00 -75.00 0.50 0.22 -- -91.75 -72.00 -82.38 172 84 \w -101.00 -71.00 0.50 0.22 -- -91.75 -71.00-138.10 60 85 \w -83.00 -54.00 0.50 0.05 -- -74.00 -71.00 15.93 58 86 \w -107.00 -71.00 0.50 0.22 -- -91.75 -71.00 102.54 72 87 \w -163.00-112.00 0.50 0.22 -- -91.75 -71.00 102.54 102 88 \w -139.00 -46.00 0.50 0.05 -- -66.00 -71.00 83.90 186 89 \w -101.00 -74.00 0.50 0.22 -- -91.75 -70.00-111.95 54 90 \w -163.00-111.00 0.50 0.22 -- -91.75 -70.00-111.95 104 91 \w -154.00 -89.00 0.50 0.22 -- -91.75 -57.00 -30.00 130 92 \w -41.00 26.00 0.50 0.05 -- -47.33 38.00-150.00 134 93 \w -81.00 18.00 0.50 0.05 -- -47.33 101.00 4.00 198 94 \w -84.00 -44.00 0.50 0.22 -- -91.75 125.00 -60.00 80 95 \w -78.00 -34.00 0.50 0.22 -- -91.75 101.00 4.00 88 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.1068175000 _diffrn_orient_matrix_UB_12 0.0841283000 _diffrn_orient_matrix_UB_13 0.0282759000 _diffrn_orient_matrix_UB_21 -0.0260247000 _diffrn_orient_matrix_UB_22 0.1099391000 _diffrn_orient_matrix_UB_23 -0.0300082000 _diffrn_orient_matrix_UB_31 -0.1701809000 _diffrn_orient_matrix_UB_32 -0.0695602000 _diffrn_orient_matrix_UB_33 -0.0131427000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.1116 _diffrn_reflns_av_unetI/netI 0.0270 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.987 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_number 93425 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.971 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 77.786 _diffrn_reflns_theta_min 2.482 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 4.312 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.42537 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.477 _exptl_crystal_description plate _exptl_crystal_F_000 1237 _exptl_crystal_size_max 0.210 _exptl_crystal_size_mid 0.110 _exptl_crystal_size_min 0.080 _refine_diff_density_max 0.327 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.056 _refine_ls_abs_structure_details ; Flack x determined using 1917 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.046(7) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.146 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 366 _refine_ls_number_reflns 5579 _refine_ls_number_restraints 8 _refine_ls_restrained_S_all 1.151 _refine_ls_R_factor_all 0.0641 _refine_ls_R_factor_gt 0.0618 _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^)+(0.0357P)^2^+3.1046P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1301 _refine_ls_wR_factor_ref 0.1312 _reflns_Friedel_coverage 0.714 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.949 _reflns_number_gt 5273 _reflns_number_total 5579 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00948c2.cif _cod_data_source_block TCA-LTAH _cod_depositor_comments 'Adding full bibliography for 7247709--7247724.cif.' _cod_database_code 7247719 _shelx_shelxl_version_number 2019/2 _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. ; _shelx_estimated_absorpt_t_min 0.465 _shelx_estimated_absorpt_t_max 0.724 _oxdiff_exptl_absorpt_empirical_full_min 0.338 _oxdiff_exptl_absorpt_empirical_full_max 3.985 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _shelx_res_file ; TITL AM230905 in P212121 shelx.res created by SHELXL-2019/2 at 18:37:01 on 18-Sep-2023 CELL 1.54184 7.6028 9.9444 35.6016 90.000 90.000 90.000 ZERR 4.00 0.0001 0.0001 0.0004 0.000 0.000 0.000 LATT -1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM 1/2 + X, 1/2 - Y, - Z SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O CL S UNIT 80 100 8 41.685 12 4 MERG 2 DFIX 0.90 0.020 O8 H8C DFIX 0.90 0.020 O8 H8D DFIX 0.90 0.020 O9 H9A DFIX 0.90 0.020 O9 H9B DFIX 0.90 0.020 O10 H10B DFIX 0.90 0.020 O10 H10A DANG 1.200 0.040 H10A O10 H10A H10B FMAP 2 PLAN 5 SIZE 0.080 0.110 0.210 ACTA BOND $H CONF L.S. 10 WGHT 0.035700 3.104600 FVAR 0.37766 C20 1 1.198440 0.460345 0.089307 11.00000 0.02278 0.03726 = 0.04390 -0.00332 -0.00083 -0.00146 C14 1 0.403219 1.097328 0.192424 11.00000 0.03825 0.04242 = 0.04504 -0.00739 -0.00072 -0.00401 C1 1 0.170573 0.786792 0.160785 11.00000 0.03708 0.04812 = 0.04388 -0.00502 -0.00363 0.00346 C8 1 0.188391 0.910725 0.099039 11.00000 0.04102 0.05409 = 0.05225 -0.00280 0.00283 -0.00754 AFIX 23 H8A 2 0.233817 0.992248 0.087650 11.00000 -1.20000 H8B 2 0.250235 0.835255 0.087924 11.00000 -1.20000 AFIX 0 C2 1 0.282692 0.678680 0.165479 11.00000 0.04220 0.05024 = 0.04522 -0.00618 -0.00306 0.00412 C15 1 0.485955 1.197181 0.169625 11.00000 0.05458 0.04949 = 0.05504 0.00803 -0.00557 -0.00920 AFIX 43 H15 2 0.424435 1.251981 0.153027 11.00000 -1.20000 AFIX 0 C12 1 0.208550 1.068293 0.191858 11.00000 0.03998 0.05541 = 0.05660 -0.00929 -0.00042 -0.00052 AFIX 23 H12A 2 0.183360 0.995403 0.209146 11.00000 -1.20000 H12B 2 0.145180 1.147206 0.200422 11.00000 -1.20000 AFIX 0 C4 1 0.062760 0.554299 0.197379 11.00000 0.06035 0.04255 = 0.04347 -0.00349 -0.00022 -0.00199 C13 1 0.523531 1.033492 0.213670 11.00000 0.04790 0.05207 = 0.05203 0.00313 -0.00527 -0.00297 C11 1 -0.124654 0.998385 0.094484 11.00000 0.06014 0.03853 = 0.10962 -0.00727 -0.02168 0.00568 AFIX 43 H11 2 -0.106810 1.084430 0.103981 11.00000 -1.20000 AFIX 0 C5 1 -0.054093 0.658805 0.193408 11.00000 0.04278 0.06659 = 0.05991 -0.00179 0.00702 -0.00345 AFIX 43 H5 2 -0.167708 0.652244 0.202913 11.00000 -1.20000 AFIX 0 C6 1 0.000486 0.773625 0.175043 11.00000 0.03976 0.05333 = 0.06474 0.00110 0.00187 0.00922 AFIX 43 H6 2 -0.078390 0.844315 0.172081 11.00000 -1.20000 AFIX 0 C16 1 0.659436 1.204439 0.174366 11.00000 0.05761 0.07439 = 0.06030 0.00792 0.00167 -0.02503 AFIX 43 H16 2 0.731898 1.263766 0.161392 11.00000 -1.20000 AFIX 0 C10 1 -0.277315 0.946114 0.082292 11.00000 0.05149 0.05216 = 0.12696 -0.00888 -0.02735 0.01145 AFIX 43 H10 2 -0.385277 0.990021 0.081650 11.00000 -1.20000 AFIX 0 C17 1 0.718399 0.355930 0.069587 11.00000 0.02191 0.04007 = 0.05587 -0.00049 -0.00524 0.00180 C19 1 1.010294 0.416626 0.098777 11.00000 0.02496 0.04019 = 0.04116 0.00027 0.00152 -0.00290 AFIX 13 H19 2 0.952459 0.490087 0.112347 11.00000 -1.20000 AFIX 0 C9 1 -0.075967 0.791078 0.075830 11.00000 0.04856 0.03740 = 0.06251 -0.00290 -0.00163 -0.00179 AFIX 43 H9 2 -0.020205 0.710402 0.070106 11.00000 -1.20000 AFIX 0 C7 1 0.227157 0.914024 0.140627 11.00000 0.03206 0.04372 = 0.05599 -0.00385 0.00054 0.00091 AFIX 13 H7 2 0.354714 0.923033 0.143690 11.00000 -1.20000 AFIX 0 C18 1 0.910252 0.391942 0.062352 11.00000 0.02342 0.04769 = 0.04507 -0.00129 -0.00135 -0.00138 AFIX 13 H18 2 0.913719 0.474572 0.047370 11.00000 -1.20000 AFIX 0 C3 1 0.231207 0.561729 0.183366 11.00000 0.05203 0.04517 = 0.04780 -0.00331 -0.00396 0.01077 AFIX 43 H3 2 0.308521 0.489813 0.185869 11.00000 -1.20000 AFIX 0 CL1 5 0.496894 0.684457 0.148457 11.00000 0.03969 0.07635 = 0.08423 0.00224 0.00873 0.01270 CL2 5 -0.000871 0.408821 0.220961 11.00000 0.09009 0.05287 = 0.06591 0.00095 0.01105 -0.01167 CL3 5 0.487302 0.902674 0.244170 11.00000 0.09206 0.08624 = 0.09217 0.04269 -0.02561 -0.02502 N1 3 0.000366 0.899032 0.090111 11.00000 0.04325 0.04437 = 0.05201 -0.00032 -0.00620 -0.00077 N2 3 -0.245887 0.817366 0.071036 11.00000 0.05323 0.05034 = 0.07461 -0.00247 -0.01325 -0.00536 O7 4 1.319533 0.384651 0.100241 11.00000 0.02342 0.05344 = 0.06984 0.00429 -0.00154 0.00073 O5 4 1.008023 0.300798 0.121817 11.00000 0.03629 0.05112 = 0.05991 0.01559 -0.00387 -0.00564 AFIX 147 H5O 2 1.105372 0.265311 0.121571 11.00000 -1.50000 AFIX 0 O6 4 1.215034 0.567988 0.071683 11.00000 0.03141 0.04644 = 0.07683 0.01189 0.00317 -0.00423 O2 4 0.638136 0.447746 0.088811 11.00000 0.02315 0.05830 = 0.09648 -0.01960 0.00456 -0.00132 AFIX 147 H2O 2 0.533041 0.429732 0.090029 11.00000 -1.50000 AFIX 0 O8 4 0.479455 0.693512 0.034857 11.00000 0.03900 0.05773 = 0.07952 0.00756 0.00618 -0.00610 O4 4 0.996731 0.289941 0.042207 11.00000 0.03281 0.08761 = 0.06144 -0.03089 -0.00266 0.00733 AFIX 147 H4O 2 0.965139 0.291926 0.020192 11.00000 -1.50000 AFIX 0 O3 4 0.652126 0.253879 0.057708 11.00000 0.03345 0.05416 = 0.11163 -0.02464 -0.00592 -0.00526 O9 4 0.269026 0.897077 0.007648 11.00000 0.07189 0.05544 = 0.07738 0.00287 -0.01454 0.00092 O10 4 0.326950 0.165631 0.031381 11.00000 0.04383 0.08109 = 0.09150 -0.03840 -0.00295 0.00437 O1 4 0.147710 1.032358 0.155216 11.00000 0.03824 0.04697 = 0.05810 -0.00569 -0.00539 0.00584 S1 6 0.733400 1.092099 0.207052 11.00000 0.03831 0.08140 = 0.07614 0.00578 -0.00668 -0.00447 O11 4 0.829846 0.038508 0.006184 0.42119 0.45777 0.21516 = 0.12615 -0.03866 -0.01341 0.05671 H9B 2 0.261627 0.976437 0.019644 11.00000 0.19779 H10B 2 0.245691 0.222584 0.038517 11.00000 0.11618 H8D 2 0.414490 0.755900 0.023703 11.00000 0.08203 H2N 2 -0.328626 0.768161 0.056076 11.00000 0.04165 H8C 2 0.412864 0.656787 0.052487 11.00000 0.12661 H9A 2 0.153410 0.891194 0.002454 11.00000 0.13858 H10A 2 0.407817 0.200567 0.048417 11.00000 0.12550 HKLF 4 REM AM230905 in P212121 REM wR2 = 0.1312, GooF = S = 1.146, Restrained GooF = 1.151 for all data REM R1 = 0.0618 for 5273 Fo > 4sig(Fo) and 0.0641 for all 5579 data REM 366 parameters refined using 8 restraints END WGHT 0.0357 3.1048 REM Highest difference peak 0.327, deepest hole -0.277, 1-sigma level 0.056 Q1 1 0.4903 0.6857 0.1115 11.00000 0.05 0.33 Q2 1 0.5051 0.6936 0.1789 11.00000 0.05 0.32 Q3 1 0.4627 0.9794 0.2578 11.00000 0.05 0.30 Q4 1 0.0094 0.4274 0.1891 11.00000 0.05 0.28 Q5 1 0.3037 0.1541 0.0572 11.00000 0.05 0.27 ; _shelx_res_checksum 25156 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 C20 C 1.1984(6) 0.4603(5) 0.08931(13) 0.0346(9) Uani 1 1 d . . . . . C14 C 0.4032(6) 1.0973(5) 0.19242(13) 0.0419(11) Uani 1 1 d . . . . . C1 C 0.1706(7) 0.7868(5) 0.16078(14) 0.0430(11) Uani 1 1 d . . . . . C8 C 0.1884(7) 0.9107(6) 0.09904(14) 0.0491(12) Uani 1 1 d . . . . . H8A H 0.233817 0.992248 0.087650 0.059 Uiso 1 1 calc R U . . . H8B H 0.250235 0.835255 0.087924 0.059 Uiso 1 1 calc R U . . . C2 C 0.2827(7) 0.6787(6) 0.16548(14) 0.0459(11) Uani 1 1 d . . . . . C15 C 0.4860(8) 1.1972(6) 0.16962(15) 0.0530(12) Uani 1 1 d . . . . . H15 H 0.424435 1.251981 0.153027 0.064 Uiso 1 1 calc R U . . . C12 C 0.2085(7) 1.0683(6) 0.19186(15) 0.0507(13) Uani 1 1 d . . . . . H12A H 0.183360 0.995403 0.209146 0.061 Uiso 1 1 calc R U . . . H12B H 0.145180 1.147206 0.200422 0.061 Uiso 1 1 calc R U . . . C4 C 0.0628(8) 0.5543(5) 0.19738(14) 0.0488(13) Uani 1 1 d . . . . . C13 C 0.5235(8) 1.0335(6) 0.21367(15) 0.0507(12) Uani 1 1 d . . . . . C11 C -0.1247(9) 0.9984(6) 0.0945(2) 0.0694(19) Uani 1 1 d . . . . . H11 H -0.106810 1.084430 0.103981 0.083 Uiso 1 1 calc R U . . . C5 C -0.0541(8) 0.6588(7) 0.19341(16) 0.0564(14) Uani 1 1 d . . . . . H5 H -0.167708 0.652244 0.202913 0.068 Uiso 1 1 calc R U . . . C6 C 0.0005(8) 0.7736(6) 0.17504(15) 0.0526(12) Uani 1 1 d . . . . . H6 H -0.078390 0.844315 0.172081 0.063 Uiso 1 1 calc R U . . . C16 C 0.6594(8) 1.2044(7) 0.17437(18) 0.0641(17) Uani 1 1 d . . . . . H16 H 0.731898 1.263766 0.161392 0.077 Uiso 1 1 calc R U . . . C10 C -0.2773(9) 0.9461(7) 0.0823(2) 0.077(2) Uani 1 1 d . . . . . H10 H -0.385277 0.990021 0.081650 0.092 Uiso 1 1 calc R U . . . C17 C 0.7184(6) 0.3559(5) 0.06959(14) 0.0393(10) Uani 1 1 d . . . . . C19 C 1.0103(6) 0.4166(5) 0.09878(12) 0.0354(9) Uani 1 1 d . . . . . H19 H 0.952459 0.490087 0.112347 0.043 Uiso 1 1 calc R U . . . C9 C -0.0760(8) 0.7911(5) 0.07583(16) 0.0495(12) Uani 1 1 d . . . . . H9 H -0.020205 0.710402 0.070106 0.059 Uiso 1 1 calc R U . . . C7 C 0.2272(6) 0.9140(5) 0.14063(14) 0.0439(11) Uani 1 1 d . . . . . H7 H 0.354714 0.923033 0.143690 0.053 Uiso 1 1 calc R U . . . C18 C 0.9103(6) 0.3919(5) 0.06235(13) 0.0387(10) Uani 1 1 d . . . . . H18 H 0.913719 0.474572 0.047370 0.046 Uiso 1 1 calc R U . . . C3 C 0.2312(8) 0.5617(5) 0.18337(14) 0.0483(12) Uani 1 1 d . . . . . H3 H 0.308521 0.489813 0.185869 0.058 Uiso 1 1 calc R U . . . Cl1 Cl 0.4969(2) 0.68446(17) 0.14846(5) 0.0668(4) Uani 1 1 d . . . . . Cl2 Cl -0.0009(3) 0.40882(15) 0.22096(4) 0.0696(4) Uani 1 1 d . . . . . Cl3 Cl 0.4873(3) 0.9027(2) 0.24417(5) 0.0902(6) Uani 1 1 d . . . . . N1 N 0.0004(6) 0.8990(4) 0.09011(11) 0.0465(9) Uani 1 1 d . . . . . N2 N -0.2459(7) 0.8174(5) 0.07104(16) 0.0594(12) Uani 1 1 d . . . . . O7 O 1.3195(4) 0.3847(4) 0.10024(11) 0.0489(9) Uani 1 1 d . . . . . O5 O 1.0080(5) 0.3008(4) 0.12182(10) 0.0491(8) Uani 1 1 d . . . . . H5O H 1.105372 0.265311 0.121571 0.074 Uiso 1 1 calc R U . . . O6 O 1.2150(5) 0.5680(4) 0.07168(11) 0.0516(9) Uani 1 1 d . . . . . O2 O 0.6381(4) 0.4477(4) 0.08881(13) 0.0593(11) Uani 1 1 d . . . . . H2O H 0.533041 0.429732 0.090029 0.089 Uiso 1 1 calc R U . . . O8 O 0.4795(5) 0.6935(4) 0.03486(13) 0.0587(10) Uani 1 1 d D . . . . O4 O 0.9967(5) 0.2899(4) 0.04221(11) 0.0606(10) Uani 1 1 d . . . . . H4O H 0.965139 0.291926 0.020192 0.091 Uiso 1 1 calc R U . . . O3 O 0.6521(5) 0.2539(4) 0.05771(14) 0.0664(12) Uani 1 1 d . . . . . O9 O 0.2690(7) 0.8971(5) 0.00765(14) 0.0682(11) Uani 1 1 d D . . . . O10 O 0.3269(6) 0.1656(5) 0.03138(14) 0.0721(13) Uani 1 1 d D . . . . O1 O 0.1477(5) 1.0324(4) 0.15522(11) 0.0478(8) Uani 1 1 d . . . . . S1 S 0.73340(19) 1.0921(2) 0.20705(5) 0.0653(4) Uani 1 1 d . . . . . O11 O 0.830(6) 0.039(3) 0.0062(7) 0.27(2) Uani 0.42(2) 1 d . . . . . H9B H 0.26(2) 0.976(7) 0.020(4) 0.20(6) Uiso 1 1 d D . . . . H10B H 0.246(8) 0.223(7) 0.039(2) 0.12(3) Uiso 1 1 d D . . . . H8D H 0.414(9) 0.756(6) 0.0237(19) 0.08(2) Uiso 1 1 d D . . . . H2N H -0.329(7) 0.768(5) 0.0561(15) 0.042(14) Uiso 1 1 d . . . . . H8C H 0.413(11) 0.657(9) 0.052(2) 0.13(4) Uiso 1 1 d D . . . . H9A H 0.153(5) 0.891(12) 0.002(3) 0.14(4) Uiso 1 1 d D . . . . H10A H 0.408(9) 0.201(9) 0.048(2) 0.13(4) Uiso 1 1 d 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 C20 0.023(2) 0.037(2) 0.044(2) -0.0033(19) -0.0008(18) -0.0015(17) C14 0.038(2) 0.042(3) 0.045(2) -0.007(2) -0.001(2) -0.004(2) C1 0.037(2) 0.048(3) 0.044(3) -0.005(2) -0.004(2) 0.003(2) C8 0.041(3) 0.054(3) 0.052(3) -0.003(3) 0.003(2) -0.008(3) C2 0.042(3) 0.050(3) 0.045(3) -0.006(2) -0.003(2) 0.004(2) C15 0.055(3) 0.049(3) 0.055(3) 0.008(2) -0.006(3) -0.009(3) C12 0.040(3) 0.055(3) 0.057(3) -0.009(3) 0.000(2) -0.001(2) C4 0.060(3) 0.043(3) 0.043(3) -0.003(2) 0.000(2) -0.002(2) C13 0.048(3) 0.052(3) 0.052(3) 0.003(2) -0.005(2) -0.003(3) C11 0.060(4) 0.039(3) 0.110(6) -0.007(3) -0.022(4) 0.006(3) C5 0.043(3) 0.067(4) 0.060(3) -0.002(3) 0.007(2) -0.003(3) C6 0.040(3) 0.053(3) 0.065(3) 0.001(2) 0.002(3) 0.009(3) C16 0.058(4) 0.074(4) 0.060(3) 0.008(3) 0.002(3) -0.025(3) C10 0.051(3) 0.052(4) 0.127(6) -0.009(4) -0.027(4) 0.011(3) C17 0.022(2) 0.040(2) 0.056(3) 0.000(2) -0.005(2) 0.0018(19) C19 0.0250(19) 0.040(2) 0.041(2) 0.0003(18) 0.0015(18) -0.003(2) C9 0.049(3) 0.037(3) 0.063(3) -0.003(2) -0.002(3) -0.002(2) C7 0.032(2) 0.044(3) 0.056(3) -0.004(2) 0.001(2) 0.001(2) C18 0.023(2) 0.048(3) 0.045(2) -0.001(2) -0.0013(18) -0.001(2) C3 0.052(3) 0.045(3) 0.048(3) -0.003(2) -0.004(2) 0.011(2) Cl1 0.0397(6) 0.0763(9) 0.0842(10) 0.0022(8) 0.0087(7) 0.0127(7) Cl2 0.0901(11) 0.0529(7) 0.0659(8) 0.0009(6) 0.0110(9) -0.0117(9) Cl3 0.0921(13) 0.0862(12) 0.0922(12) 0.0427(10) -0.0256(11) -0.0250(12) N1 0.043(2) 0.044(2) 0.052(2) -0.0003(18) -0.006(2) -0.001(2) N2 0.053(3) 0.050(3) 0.075(3) -0.002(2) -0.013(3) -0.005(2) O7 0.0234(16) 0.053(2) 0.070(2) 0.0043(18) -0.0015(15) 0.0007(15) O5 0.0363(17) 0.0511(19) 0.060(2) 0.0156(16) -0.0039(18) -0.0056(18) O6 0.0314(17) 0.046(2) 0.077(2) 0.0119(18) 0.0032(16) -0.0042(16) O2 0.0231(16) 0.058(2) 0.096(3) -0.020(2) 0.0046(19) -0.0013(16) O8 0.039(2) 0.058(2) 0.080(3) 0.008(2) 0.006(2) -0.006(2) O4 0.0328(18) 0.088(3) 0.061(2) -0.031(2) -0.0027(19) 0.007(2) O3 0.0335(19) 0.054(2) 0.112(4) -0.025(2) -0.006(2) -0.0053(18) O9 0.072(3) 0.055(3) 0.077(3) 0.003(2) -0.015(2) 0.001(2) O10 0.044(2) 0.081(3) 0.091(3) -0.038(3) -0.003(2) 0.004(2) O1 0.0382(18) 0.047(2) 0.058(2) -0.0057(17) -0.0054(16) 0.0058(15) S1 0.0383(7) 0.0814(11) 0.0761(9) 0.0058(9) -0.0067(7) -0.0045(7) O11 0.46(6) 0.22(3) 0.126(19) -0.04(2) -0.01(3) 0.06(4) 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' Cl Cl 0.3639 0.7018 '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 O6 C20 O7 126.8(4) . . ? O6 C20 C19 116.7(4) . . ? O7 C20 C19 116.6(4) . . ? C13 C14 C15 110.4(5) . . ? C13 C14 C12 125.7(5) . . ? C15 C14 C12 123.9(5) . . ? C2 C1 C6 117.0(5) . . ? C2 C1 C7 122.1(5) . . ? C6 C1 C7 120.9(5) . . ? N1 C8 C7 113.8(4) . . ? N1 C8 H8A 108.8 . . ? C7 C8 H8A 108.8 . . ? N1 C8 H8B 108.8 . . ? C7 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? C1 C2 C3 122.4(5) . . ? C1 C2 Cl1 120.7(4) . . ? C3 C2 Cl1 117.0(4) . . ? C16 C15 C14 113.7(5) . . ? C16 C15 H15 123.2 . . ? C14 C15 H15 123.2 . . ? O1 C12 C14 112.2(4) . . ? O1 C12 H12A 109.2 . . ? C14 C12 H12A 109.2 . . ? O1 C12 H12B 109.2 . . ? C14 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C5 C4 C3 121.6(5) . . ? C5 C4 Cl2 119.9(5) . . ? C3 C4 Cl2 118.5(4) . . ? C14 C13 S1 113.3(4) . . ? C14 C13 Cl3 127.1(5) . . ? S1 C13 Cl3 119.6(3) . . ? C10 C11 N1 106.4(5) . . ? C10 C11 H11 126.8 . . ? N1 C11 H11 126.8 . . ? C4 C5 C6 118.7(5) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C5 C6 C1 121.9(5) . . ? C5 C6 H6 119.0 . . ? C1 C6 H6 119.0 . . ? C15 C16 S1 112.1(5) . . ? C15 C16 H16 123.9 . . ? S1 C16 H16 123.9 . . ? C11 C10 N2 107.9(6) . . ? C11 C10 H10 126.1 . . ? N2 C10 H10 126.1 . . ? O3 C17 O2 125.5(4) . . ? O3 C17 C18 122.5(5) . . ? O2 C17 C18 112.0(4) . . ? O5 C19 C18 110.9(4) . . ? O5 C19 C20 111.7(4) . . ? C18 C19 C20 108.9(3) . . ? O5 C19 H19 108.4 . . ? C18 C19 H19 108.4 . . ? C20 C19 H19 108.4 . . ? N1 C9 N2 108.4(5) . . ? N1 C9 H9 125.8 . . ? N2 C9 H9 125.8 . . ? O1 C7 C8 107.1(4) . . ? O1 C7 C1 113.4(4) . . ? C8 C7 C1 113.0(4) . . ? O1 C7 H7 107.7 . . ? C8 C7 H7 107.7 . . ? C1 C7 H7 107.7 . . ? O4 C18 C19 108.5(4) . . ? O4 C18 C17 111.4(4) . . ? C19 C18 C17 111.8(4) . . ? O4 C18 H18 108.3 . . ? C19 C18 H18 108.3 . . ? C17 C18 H18 108.3 . . ? C4 C3 C2 118.4(5) . . ? C4 C3 H3 120.8 . . ? C2 C3 H3 120.8 . . ? C9 N1 C11 108.8(5) . . ? C9 N1 C8 125.1(5) . . ? C11 N1 C8 126.1(5) . . ? C9 N2 C10 108.5(5) . . ? C9 N2 H2N 128(3) . . ? C10 N2 H2N 122(3) . . ? C19 O5 H5O 109.5 . . ? C17 O2 H2O 109.5 . . ? H8D O8 H8C 107(8) . . ? C18 O4 H4O 109.5 . . ? H9B O9 H9A 95(10) . . ? H10B O10 H10A 92(5) . . ? C7 O1 C12 113.8(4) . . ? C16 S1 C13 90.5(3) . . ? 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 C20 O6 1.247(6) . ? C20 O7 1.251(6) . ? C20 C19 1.533(6) . ? C14 C13 1.346(7) . ? C14 C15 1.428(7) . ? C14 C12 1.508(7) . ? C1 C2 1.382(7) . ? C1 C6 1.395(8) . ? C1 C7 1.517(7) . ? C8 N1 1.469(7) . ? C8 C7 1.510(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C2 C3 1.382(8) . ? C2 Cl1 1.739(5) . ? C15 C16 1.332(9) . ? C15 H15 0.9300 . ? C12 O1 1.429(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C4 C5 1.375(8) . ? C4 C3 1.376(8) . ? C4 Cl2 1.741(6) . ? C13 S1 1.715(6) . ? C13 Cl3 1.717(6) . ? C11 C10 1.344(9) . ? C11 N1 1.380(8) . ? C11 H11 0.9300 . ? C5 C6 1.380(8) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C16 S1 1.708(7) . ? C16 H16 0.9300 . ? C10 N2 1.363(8) . ? C10 H10 0.9300 . ? C17 O3 1.209(6) . ? C17 O2 1.294(6) . ? C17 C18 1.524(6) . ? C19 O5 1.414(5) . ? C19 C18 1.523(6) . ? C19 H19 0.9800 . ? C9 N1 1.322(7) . ? C9 N2 1.329(8) . ? C9 H9 0.9300 . ? C7 O1 1.421(6) . ? C7 H7 0.9800 . ? C18 O4 1.406(6) . ? C18 H18 0.9800 . ? C3 H3 0.9300 . ? N2 H2N 0.96(6) . ? O5 H5O 0.8200 . ? O2 H2O 0.8200 . ? O8 H8D 0.89(3) . ? O8 H8C 0.89(3) . ? O4 H4O 0.8200 . ? O9 H9B 0.90(3) . ? O9 H9A 0.90(3) . ? O10 H10B 0.88(3) . ? O10 H10A 0.93(2) . ? 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 C6 C1 C2 C3 0.1(8) . . . . ? C7 C1 C2 C3 -179.1(5) . . . . ? C6 C1 C2 Cl1 179.6(4) . . . . ? C7 C1 C2 Cl1 0.4(7) . . . . ? C13 C14 C15 C16 0.1(7) . . . . ? C12 C14 C15 C16 -179.2(6) . . . . ? C13 C14 C12 O1 -121.6(6) . . . . ? C15 C14 C12 O1 57.5(7) . . . . ? C15 C14 C13 S1 0.5(6) . . . . ? C12 C14 C13 S1 179.8(4) . . . . ? C15 C14 C13 Cl3 -177.7(4) . . . . ? C12 C14 C13 Cl3 1.6(9) . . . . ? C3 C4 C5 C6 -0.3(8) . . . . ? Cl2 C4 C5 C6 179.1(4) . . . . ? C4 C5 C6 C1 -0.6(9) . . . . ? C2 C1 C6 C5 0.7(8) . . . . ? C7 C1 C6 C5 179.9(5) . . . . ? C14 C15 C16 S1 -0.6(8) . . . . ? N1 C11 C10 N2 0.5(9) . . . . ? O6 C20 C19 O5 -174.3(4) . . . . ? O7 C20 C19 O5 5.4(6) . . . . ? O6 C20 C19 C18 62.9(5) . . . . ? O7 C20 C19 C18 -117.5(5) . . . . ? N1 C8 C7 O1 -63.7(6) . . . . ? N1 C8 C7 C1 61.9(6) . . . . ? C2 C1 C7 O1 -146.9(5) . . . . ? C6 C1 C7 O1 34.0(6) . . . . ? C2 C1 C7 C8 91.1(6) . . . . ? C6 C1 C7 C8 -88.1(6) . . . . ? O5 C19 C18 O4 -63.2(5) . . . . ? C20 C19 C18 O4 60.1(5) . . . . ? O5 C19 C18 C17 60.0(5) . . . . ? C20 C19 C18 C17 -176.7(4) . . . . ? O3 C17 C18 O4 -2.7(7) . . . . ? O2 C17 C18 O4 178.6(4) . . . . ? O3 C17 C18 C19 -124.3(6) . . . . ? O2 C17 C18 C19 57.1(6) . . . . ? C5 C4 C3 C2 1.0(8) . . . . ? Cl2 C4 C3 C2 -178.4(4) . . . . ? C1 C2 C3 C4 -0.9(8) . . . . ? Cl1 C2 C3 C4 179.6(4) . . . . ? N2 C9 N1 C11 -0.3(7) . . . . ? N2 C9 N1 C8 -179.2(5) . . . . ? C10 C11 N1 C9 -0.1(8) . . . . ? C10 C11 N1 C8 178.8(6) . . . . ? C7 C8 N1 C9 -109.4(6) . . . . ? C7 C8 N1 C11 71.9(8) . . . . ? N1 C9 N2 C10 0.6(7) . . . . ? C11 C10 N2 C9 -0.7(9) . . . . ? C8 C7 O1 C12 -165.0(4) . . . . ? C1 C7 O1 C12 69.7(5) . . . . ? C14 C12 O1 C7 61.4(6) . . . . ? C15 C16 S1 C13 0.8(6) . . . . ? C14 C13 S1 C16 -0.7(5) . . . . ? Cl3 C13 S1 C16 177.6(4) . . . . ?