#------------------------------------------------------------------------------ #$Date: 2024-01-06 10:01:35 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288801 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247722.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_7247722 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 H3 O4, O' _chemical_formula_sum 'C20 H17 Cl3 N2 O6 S' _chemical_formula_weight 519.77 _chemical_name_common 'Tioconazole-Fumerate salt monohydrate' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary direct _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2023-07-31 deposited with the CCDC. 2023-11-14 downloaded from the CCDC. ; _cell_angle_alpha 94.572(2) _cell_angle_beta 98.318(2) _cell_angle_gamma 94.709(3) _cell_formula_units_Z 2 _cell_length_a 7.4874(2) _cell_length_b 8.0833(3) _cell_length_c 19.8791(5) _cell_measurement_reflns_used 13045 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 71.9910 _cell_measurement_theta_min 2.2500 _cell_volume 1181.34(6) _computing_cell_refinement 'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)' _computing_data_collection 'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)' _computing_data_reduction 'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)' _computing_molecular_graphics 'Ortep for Windows (Farrugia, 2012)' _computing_publication_material 'WinGX publication routines (Farrugia, 2012)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXS-2013/1 (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector CCD _diffrn_detector_area_resol_mean 28.5714 _diffrn_measured_fraction_theta_full 0.962 _diffrn_measured_fraction_theta_max 0.934 _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 -130.00 -10.00 1.00 4.00 -- -40.00 -72.00 0.00 120 2 \w -130.00 -10.00 1.00 4.00 -- -40.00 -72.00 70.00 120 3 \w -130.00 -10.00 1.00 4.00 -- -40.00 -72.00 140.00 120 4 \w -130.00 -10.00 1.00 4.00 -- -40.00 -72.00 210.00 120 5 \w -130.00 -10.00 1.00 4.00 -- -40.00 -72.00 280.00 120 6 \w -130.00 50.00 1.00 4.00 -- -40.00 0.00 0.00 180 7 \w -100.00 20.00 1.00 4.00 -- -70.00 72.00 0.00 120 8 \w -100.00 20.00 1.00 4.00 -- -70.00 72.00 70.00 120 9 \w -100.00 20.00 1.00 4.00 -- -70.00 72.00 140.00 120 10 \w -100.00 20.00 1.00 4.00 -- -70.00 72.00 210.00 120 11 \w -100.00 20.00 1.00 4.00 -- -70.00 72.00 280.00 120 12 \w -160.00 20.00 1.00 4.00 -- -70.00 0.00 0.00 180 13 \w -190.00 -70.00 1.00 4.00 -- -100.00 -72.00 0.00 120 14 \w -190.00 -70.00 1.00 4.00 -- -100.00 -72.00 70.00 120 15 \w -190.00 -70.00 1.00 4.00 -- -100.00 -72.00 140.00 120 16 \w -190.00 -70.00 1.00 4.00 -- -100.00 -72.00 210.00 120 17 \w -190.00 -70.00 1.00 4.00 -- -100.00 -72.00 280.00 120 18 \w -130.00 -10.00 1.00 4.00 -- -100.00 72.00 0.00 120 19 \w -130.00 -10.00 1.00 4.00 -- -100.00 72.00 70.00 120 20 \w -130.00 -10.00 1.00 4.00 -- -100.00 72.00 140.00 120 21 \w -130.00 -10.00 1.00 4.00 -- -100.00 72.00 210.00 120 22 \w -130.00 -10.00 1.00 4.00 -- -100.00 72.00 280.00 120 23 \w -190.00 -10.00 1.00 4.00 -- -100.00 0.00 0.00 180 ; _diffrn_measurement_device ; AFC12 (Right): Kappa 3 circle ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (4x4 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support Loop _diffrn_radiation_monochromator Confocal _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.1204 _diffrn_reflns_av_unetI/netI 0.0639 _diffrn_reflns_Laue_measured_fraction_full 0.962 _diffrn_reflns_Laue_measured_fraction_max 0.934 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 23733 _diffrn_reflns_point_group_measured_fraction_full 0.962 _diffrn_reflns_point_group_measured_fraction_max 0.934 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 72.787 _diffrn_reflns_theta_min 2.256 _diffrn_source MicroMax003_Cu _diffrn_source_current 0.6 _diffrn_source_power 0.0 _diffrn_source_voltage 50.0 _exptl_absorpt_coefficient_mu 4.684 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.44547 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.461 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 532 _exptl_crystal_size_max 0.410 _exptl_crystal_size_mid 0.380 _exptl_crystal_size_min 0.330 _refine_diff_density_max 0.701 _refine_diff_density_min -0.532 _refine_diff_density_rms 0.122 _refine_ls_extinction_coef 0.0155(17) _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 1.047 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 296 _refine_ls_number_reflns 4386 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.047 _refine_ls_R_factor_all 0.0836 _refine_ls_R_factor_gt 0.0726 _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^)+(0.1222P)^2^+0.5265P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1881 _refine_ls_wR_factor_ref 0.2029 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3561 _reflns_number_total 4386 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00948c2.cif _cod_data_source_block TCZ-FUMH1 _cod_depositor_comments 'Adding full bibliography for 7247709--7247724.cif.' _cod_database_code 7247722 _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_min 0.250 _shelx_estimated_absorpt_t_max 0.307 _shelx_res_file ; TITL AM20220712b_Cu in P-1 shelx.res created by SHELXL-2018/3 at 09:52:20 on 01-Aug-2022 CELL 1.54184 7.4874 8.0833 19.8791 94.572 98.318 94.709 ZERR 2.00 0.0002 0.0003 0.0005 0.002 0.002 0.003 LATT 1 SFAC C H N O S CL UNIT 40 34 4 12 2 6 MERG 2 OMIT 2 -1 1 FMAP 2 PLAN 2 SIZE 0.330 0.380 0.410 ACTA BOND $H CONF L.S. 10 TEMP 20.00 WGHT 0.122200 0.526500 EXTI 0.015495 FVAR 4.62480 0.39585 C1 1 0.929260 0.300008 0.350230 11.00000 0.04690 0.04534 = 0.05251 0.00608 0.01382 0.01415 C2 1 0.835078 0.251605 0.401716 11.00000 0.05426 0.03964 = 0.06080 0.00559 0.01756 0.00934 C3 1 0.768714 0.365962 0.445137 11.00000 0.06206 0.05270 = 0.05806 0.00680 0.02461 0.01440 AFIX 43 H3 2 0.704483 0.331015 0.478967 11.00000 -1.20000 AFIX 0 C4 1 0.800213 0.531672 0.436909 11.00000 0.06714 0.04780 = 0.05739 0.00136 0.01854 0.02030 C5 1 0.897080 0.585553 0.388172 11.00000 0.08808 0.04338 = 0.07182 0.00608 0.02857 0.01740 AFIX 43 H5 2 0.919996 0.698893 0.384167 11.00000 -1.20000 AFIX 0 C6 1 0.960628 0.468500 0.344799 11.00000 0.07445 0.04776 = 0.06708 0.01625 0.03091 0.01679 AFIX 43 H6 2 1.025723 0.504528 0.311381 11.00000 -1.20000 AFIX 0 C7 1 0.989206 0.171664 0.300075 11.00000 0.04933 0.04938 = 0.05326 0.00538 0.01910 0.01465 AFIX 13 H7 2 1.025432 0.075247 0.323834 11.00000 -1.20000 AFIX 0 C8 1 0.833205 0.116386 0.243521 11.00000 0.05563 0.06062 = 0.06910 -0.00331 0.00782 0.02097 AFIX 23 H8A 2 0.723563 0.092935 0.263142 11.00000 -1.20000 H8B 2 0.813884 0.205773 0.214270 11.00000 -1.20000 AFIX 0 C9 1 0.925178 -0.036822 0.142393 11.00000 0.07353 0.07562 = 0.06055 0.00900 0.01427 0.00243 AFIX 43 H9 2 0.943329 0.054552 0.117730 11.00000 -1.20000 AFIX 0 C10 1 0.910777 -0.290621 0.172229 11.00000 0.07460 0.05698 = 0.08319 -0.00705 0.01830 0.00907 AFIX 43 H10 2 0.916561 -0.405216 0.171565 11.00000 -1.20000 AFIX 0 C11 1 0.861181 -0.190957 0.221549 11.00000 0.07360 0.06227 = 0.06746 0.00538 0.02492 0.01423 AFIX 43 H11 2 0.827114 -0.224094 0.261971 11.00000 -1.20000 AFIX 0 C12 1 1.309217 0.205067 0.302991 11.00000 0.04734 0.06186 = 0.06110 0.00360 0.01729 0.00958 AFIX 23 H12A 2 1.315196 0.230453 0.351831 11.00000 -1.20000 H12B 2 1.403139 0.276819 0.288003 11.00000 -1.20000 AFIX 0 C13 1 1.351155 -0.088865 0.333620 11.00000 0.05628 0.06790 = 0.07494 0.00948 0.02246 0.01926 C14 1 1.343648 0.027261 0.288657 11.00000 0.04000 0.05850 = 0.06466 0.00208 0.01652 0.01002 C15 1 1.372411 -0.042381 0.223123 11.00000 0.05159 0.07521 = 0.06942 -0.00723 0.01767 0.00937 AFIX 43 H15 2 1.371271 0.018114 0.185207 11.00000 -1.20000 AFIX 0 C16 1 1.401373 -0.205040 0.222061 11.00000 0.06632 0.07886 = 0.09170 -0.02027 0.02065 0.01416 AFIX 43 H16 2 1.422359 -0.268922 0.183471 11.00000 -1.20000 AFIX 0 C17 1 0.986654 0.321862 0.045623 11.00000 0.04714 0.06458 = 0.05188 0.00849 0.01738 0.01889 C18 1 1.190520 0.341052 0.056692 11.00000 0.04638 0.08571 = 0.05567 0.00941 0.01836 0.01769 AFIX 43 H18 2 1.249707 0.336381 0.018650 11.00000 -1.20000 AFIX 0 C19 1 1.288334 0.363957 0.117170 11.00000 0.04705 0.07371 = 0.05383 0.00973 0.01715 0.01588 AFIX 43 H19 2 1.227994 0.374310 0.154806 11.00000 -1.20000 AFIX 0 C20 1 1.488845 0.374560 0.129875 11.00000 0.05024 0.06952 = 0.05881 0.01173 0.01508 0.01961 N1 3 0.868798 -0.032336 0.202772 11.00000 0.05475 0.05944 = 0.05407 -0.00002 0.01250 0.01317 N2 3 0.951362 -0.192043 0.122970 11.00000 0.06792 0.08169 = 0.05992 -0.01503 0.01575 0.00908 O1 4 1.136227 0.238861 0.269230 11.00000 0.05301 0.06296 = 0.05569 0.01349 0.02009 0.01800 O2 4 0.907896 0.277193 -0.013309 11.00000 0.05171 0.13014 = 0.05771 -0.01051 0.01332 0.00987 O3 4 0.908069 0.349940 0.095991 11.00000 0.04453 0.09450 = 0.05710 0.00200 0.01947 0.01719 O4 4 1.562835 0.353743 0.074874 11.00000 0.04230 0.17105 = 0.06492 -0.00532 0.01661 0.02125 AFIX 148 H4 2 1.683450 0.358570 0.086253 11.00000 -1.50000 AFIX 0 O5 4 1.573026 0.401652 0.186683 11.00000 0.05366 0.11540 = 0.06231 0.01118 0.00871 0.01857 S1 5 1.395122 -0.280246 0.299582 11.00000 0.07588 0.06138 = 0.12292 0.00418 0.02613 0.02295 CL1 6 0.798931 0.042055 0.414366 11.00000 0.09424 0.04455 = 0.10125 0.01362 0.05262 0.01084 CL2 6 0.716647 0.676638 0.490983 11.00000 0.10794 0.06034 = 0.07869 -0.00537 0.03629 0.02945 CL3 6 1.318502 -0.062994 0.417960 11.00000 0.09138 0.09563 = 0.07412 0.02740 0.03033 0.03037 O6A 4 1.528492 0.202083 -0.065192 21.00000 0.12957 O6B 4 1.544853 0.082653 -0.057035 -21.00000 0.17323 H2N 2 1.008595 -0.221566 0.079294 11.00000 0.11131 HKLF 4 REM AM20220712b_Cu in P-1 REM wR2 = 0.2029, GooF = S = 1.047, Restrained GooF = 1.047 for all data REM R1 = 0.0726 for 3561 Fo > 4sig(Fo) and 0.0836 for all 4386 data REM 296 parameters refined using 0 restraints END WGHT 0.1222 0.5265 REM Highest difference peak 0.701, deepest hole -0.532, 1-sigma level 0.122 Q1 1 1.3139 -0.1503 0.3910 11.00000 0.05 0.70 Q2 1 1.5255 0.1239 -0.0681 11.00000 0.05 0.46 ; _shelx_res_checksum 6764 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.9293(4) 0.3000(4) 0.35023(15) 0.0470(7) Uani 1 1 d . . . . . C2 C 0.8351(4) 0.2516(4) 0.40172(16) 0.0504(7) Uani 1 1 d . . . . . C3 C 0.7687(4) 0.3660(4) 0.44514(16) 0.0555(8) Uani 1 1 d . . . . . H3 H 0.704483 0.331015 0.478967 0.067 Uiso 1 1 calc R U . . . C4 C 0.8002(5) 0.5317(4) 0.43691(16) 0.0559(8) Uani 1 1 d . . . . . C5 C 0.8971(5) 0.5856(4) 0.38817(19) 0.0655(9) Uani 1 1 d . . . . . H5 H 0.919996 0.698893 0.384167 0.079 Uiso 1 1 calc R U . . . C6 C 0.9606(5) 0.4685(4) 0.34480(17) 0.0599(8) Uani 1 1 d . . . . . H6 H 1.025723 0.504528 0.311381 0.072 Uiso 1 1 calc R U . . . C7 C 0.9892(4) 0.1717(4) 0.30007(15) 0.0489(7) Uani 1 1 d . . . . . H7 H 1.025432 0.075247 0.323834 0.059 Uiso 1 1 calc R U . . . C8 C 0.8332(5) 0.1164(4) 0.24352(18) 0.0616(9) Uani 1 1 d . . . . . H8A H 0.723563 0.092935 0.263142 0.074 Uiso 1 1 calc R U . . . H8B H 0.813884 0.205773 0.214270 0.074 Uiso 1 1 calc R U . . . C9 C 0.9252(5) -0.0368(5) 0.14239(19) 0.0696(10) Uani 1 1 d . . . . . H9 H 0.943329 0.054552 0.117730 0.084 Uiso 1 1 calc R U . . . C10 C 0.9108(5) -0.2906(5) 0.1722(2) 0.0715(10) Uani 1 1 d . . . . . H10 H 0.916561 -0.405216 0.171565 0.086 Uiso 1 1 calc R U . . . C11 C 0.8612(5) -0.1910(5) 0.22155(19) 0.0660(9) Uani 1 1 d . . . . . H11 H 0.827114 -0.224094 0.261971 0.079 Uiso 1 1 calc R U . . . C12 C 1.3092(4) 0.2051(4) 0.30299(17) 0.0557(8) Uani 1 1 d . . . . . H12A H 1.315196 0.230453 0.351831 0.067 Uiso 1 1 calc R U . . . H12B H 1.403139 0.276819 0.288003 0.067 Uiso 1 1 calc R U . . . C13 C 1.3512(5) -0.0889(5) 0.33362(19) 0.0642(9) Uani 1 1 d . . . . . C14 C 1.3436(4) 0.0273(4) 0.28866(17) 0.0534(8) Uani 1 1 d . . . . . C15 C 1.3724(4) -0.0424(5) 0.22312(19) 0.0651(9) Uani 1 1 d . . . . . H15 H 1.371271 0.018114 0.185207 0.078 Uiso 1 1 calc R U . . . C16 C 1.4014(5) -0.2050(6) 0.2221(2) 0.0792(12) Uani 1 1 d . . . . . H16 H 1.422359 -0.268922 0.183471 0.095 Uiso 1 1 calc R U . . . C17 C 0.9867(4) 0.3219(4) 0.04562(15) 0.0526(8) Uani 1 1 d . . . . . C18 C 1.1905(4) 0.3411(5) 0.05669(17) 0.0607(9) Uani 1 1 d . . . . . H18 H 1.249707 0.336381 0.018650 0.073 Uiso 1 1 calc R U . . . C19 C 1.2883(4) 0.3640(5) 0.11717(16) 0.0565(8) Uani 1 1 d . . . . . H19 H 1.227994 0.374310 0.154806 0.068 Uiso 1 1 calc R U . . . C20 C 1.4888(4) 0.3746(5) 0.12988(17) 0.0578(8) Uani 1 1 d . . . . . N1 N 0.8688(4) -0.0323(4) 0.20277(13) 0.0555(7) Uani 1 1 d . . . . . N2 N 0.9514(4) -0.1920(4) 0.12297(16) 0.0703(9) Uani 1 1 d . . . . . O1 O 1.1362(3) 0.2389(3) 0.26923(10) 0.0549(6) Uani 1 1 d . . . . . O2 O 0.9079(3) 0.2772(4) -0.01331(12) 0.0803(8) Uani 1 1 d . . . . . O3 O 0.9081(3) 0.3499(3) 0.09599(11) 0.0639(6) Uani 1 1 d . . . . . O4 O 1.5628(3) 0.3537(5) 0.07487(13) 0.0922(11) Uani 1 1 d . . . . . H4 H 1.683(9) 0.359(8) 0.0863(9) 0.138 Uiso 1 1 calc R U . . . O5 O 1.5730(3) 0.4017(4) 0.18668(13) 0.0764(8) Uani 1 1 d . . . . . S1 S 1.39512(15) -0.28025(13) 0.29958(7) 0.0850(4) Uani 1 1 d . . . . . Cl1 Cl 0.79893(14) 0.04206(11) 0.41437(5) 0.0757(4) Uani 1 1 d . . . . . Cl2 Cl 0.71665(16) 0.67664(12) 0.49098(5) 0.0796(4) Uani 1 1 d . . . . . Cl3 Cl 1.31850(15) -0.06299(15) 0.41796(5) 0.0830(4) Uani 1 1 d . . . . . O6A O 1.5285(17) 0.202(2) -0.0652(6) 0.130(6) Uiso 0.40(2) 1 d . . P . . O6B O 1.5449(15) 0.083(2) -0.0570(5) 0.173(5) Uiso 0.60(2) 1 d . . P . . H2N H 1.009(7) -0.222(7) 0.079(3) 0.111(16) Uiso 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0469(15) 0.0453(17) 0.0525(15) 0.0061(12) 0.0138(12) 0.0141(12) C2 0.0543(16) 0.0396(17) 0.0608(17) 0.0056(13) 0.0176(13) 0.0093(12) C3 0.0621(18) 0.053(2) 0.0581(17) 0.0068(14) 0.0246(14) 0.0144(14) C4 0.0671(19) 0.0478(19) 0.0574(17) 0.0014(13) 0.0185(14) 0.0203(14) C5 0.088(2) 0.0434(19) 0.072(2) 0.0061(15) 0.0286(18) 0.0174(16) C6 0.074(2) 0.048(2) 0.0671(19) 0.0162(15) 0.0309(16) 0.0168(15) C7 0.0493(15) 0.0494(17) 0.0533(16) 0.0054(13) 0.0191(12) 0.0147(12) C8 0.0556(18) 0.061(2) 0.069(2) -0.0033(16) 0.0078(15) 0.0210(15) C9 0.074(2) 0.076(3) 0.0606(19) 0.0090(18) 0.0143(17) 0.0024(18) C10 0.075(2) 0.057(2) 0.083(2) -0.0070(19) 0.0183(19) 0.0091(17) C11 0.074(2) 0.062(2) 0.067(2) 0.0054(17) 0.0249(17) 0.0142(17) C12 0.0473(15) 0.062(2) 0.0611(17) 0.0036(15) 0.0173(13) 0.0096(14) C13 0.0563(18) 0.068(2) 0.075(2) 0.0095(18) 0.0225(16) 0.0193(16) C14 0.0400(14) 0.058(2) 0.0647(18) 0.0021(15) 0.0165(13) 0.0100(13) C15 0.0516(17) 0.075(2) 0.069(2) -0.0072(17) 0.0177(15) 0.0094(16) C16 0.066(2) 0.079(3) 0.092(3) -0.020(2) 0.021(2) 0.0142(19) C17 0.0471(15) 0.065(2) 0.0519(16) 0.0085(14) 0.0174(13) 0.0189(14) C18 0.0464(16) 0.086(3) 0.0557(17) 0.0094(16) 0.0184(13) 0.0177(16) C19 0.0471(16) 0.074(2) 0.0538(17) 0.0097(15) 0.0172(13) 0.0159(14) C20 0.0502(16) 0.070(2) 0.0588(18) 0.0117(15) 0.0151(14) 0.0196(15) N1 0.0547(14) 0.0594(18) 0.0541(14) 0.0000(12) 0.0125(11) 0.0132(12) N2 0.0679(18) 0.082(2) 0.0599(16) -0.0150(16) 0.0158(14) 0.0091(15) O1 0.0530(12) 0.0630(14) 0.0557(11) 0.0135(10) 0.0201(9) 0.0180(10) O2 0.0517(13) 0.130(3) 0.0577(14) -0.0105(14) 0.0133(11) 0.0099(14) O3 0.0445(11) 0.0945(18) 0.0571(12) 0.0020(12) 0.0195(9) 0.0172(11) O4 0.0423(12) 0.171(3) 0.0649(15) -0.0053(17) 0.0166(11) 0.0213(16) O5 0.0537(13) 0.115(2) 0.0623(14) 0.0112(14) 0.0087(11) 0.0186(13) S1 0.0759(7) 0.0614(7) 0.1229(9) 0.0042(6) 0.0261(6) 0.0230(5) Cl1 0.0942(7) 0.0446(6) 0.1012(7) 0.0136(4) 0.0526(5) 0.0108(4) Cl2 0.1079(8) 0.0603(6) 0.0787(6) -0.0054(4) 0.0363(5) 0.0295(5) Cl3 0.0914(7) 0.0956(8) 0.0741(6) 0.0274(5) 0.0303(5) 0.0304(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' Cl Cl 0.3639 0.7018 '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 C6 C1 C2 117.5(3) . . ? C6 C1 C7 121.3(3) . . ? C2 C1 C7 121.1(3) . . ? C3 C2 C1 122.2(3) . . ? C3 C2 Cl1 117.5(2) . . ? C1 C2 Cl1 120.3(2) . . ? C4 C3 C2 118.2(3) . . ? C4 C3 H3 120.9 . . ? C2 C3 H3 120.9 . . ? C3 C4 C5 121.7(3) . . ? C3 C4 Cl2 118.6(3) . . ? C5 C4 Cl2 119.7(3) . . ? C4 C5 C6 119.0(3) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C1 C6 C5 121.4(3) . . ? C1 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? O1 C7 C8 107.4(2) . . ? O1 C7 C1 111.8(2) . . ? C8 C7 C1 109.1(2) . . ? O1 C7 H7 109.5 . . ? C8 C7 H7 109.5 . . ? C1 C7 H7 109.5 . . ? N1 C8 C7 111.3(2) . . ? N1 C8 H8A 109.4 . . ? C7 C8 H8A 109.4 . . ? N1 C8 H8B 109.4 . . ? C7 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? N2 C9 N1 109.0(3) . . ? N2 C9 H9 125.5 . . ? N1 C9 H9 125.5 . . ? C11 C10 N2 106.7(4) . . ? C11 C10 H10 126.7 . . ? N2 C10 H10 126.7 . . ? C10 C11 N1 108.5(3) . . ? C10 C11 H11 125.7 . . ? N1 C11 H11 125.7 . . ? O1 C12 C14 111.8(3) . . ? 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 . . ? C14 C13 S1 113.5(3) . . ? C14 C13 Cl3 126.9(3) . . ? S1 C13 Cl3 119.5(2) . . ? C13 C14 C15 110.7(3) . . ? C13 C14 C12 126.1(3) . . ? C15 C14 C12 123.2(3) . . ? C16 C15 C14 112.9(4) . . ? C16 C15 H15 123.5 . . ? C14 C15 H15 123.5 . . ? C15 C16 S1 112.3(3) . . ? C15 C16 H16 123.8 . . ? S1 C16 H16 123.8 . . ? O2 C17 O3 124.5(3) . . ? O2 C17 C18 117.5(3) . . ? O3 C17 C18 118.1(3) . . ? C19 C18 C17 123.1(3) . . ? C19 C18 H18 118.5 . . ? C17 C18 H18 118.5 . . ? C18 C19 C20 124.4(3) . . ? C18 C19 H19 117.8 . . ? C20 C19 H19 117.8 . . ? O5 C20 O4 124.2(3) . . ? O5 C20 C19 121.7(3) . . ? O4 C20 C19 114.1(3) . . ? C9 N1 C11 107.2(3) . . ? C9 N1 C8 126.4(3) . . ? C11 N1 C8 126.3(3) . . ? C9 N2 C10 108.5(3) . . ? C9 N2 H2N 122(3) . . ? C10 N2 H2N 130(3) . . ? C7 O1 C12 113.1(2) . . ? C20 O4 H4 109.5 . . ? C16 S1 C13 90.55(19) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.378(5) . ? C1 C2 1.388(4) . ? C1 C7 1.521(4) . ? C2 C3 1.385(4) . ? C2 Cl1 1.737(3) . ? C3 C4 1.368(5) . ? C3 H3 0.9300 . ? C4 C5 1.369(5) . ? C4 Cl2 1.742(3) . ? C5 C6 1.388(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O1 1.426(4) . ? C7 C8 1.511(4) . ? C7 H7 0.9800 . ? C8 N1 1.460(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N2 1.322(5) . ? C9 N1 1.328(5) . ? C9 H9 0.9300 . ? C10 C11 1.333(5) . ? C10 N2 1.363(6) . ? C10 H10 0.9300 . ? C11 N1 1.363(5) . ? C11 H11 0.9300 . ? C12 O1 1.428(4) . ? C12 C14 1.493(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.346(5) . ? C13 S1 1.715(4) . ? C13 Cl3 1.728(4) . ? C14 C15 1.430(5) . ? C15 C16 1.349(6) . ? C15 H15 0.9300 . ? C16 S1 1.706(5) . ? C16 H16 0.9300 . ? C17 O2 1.244(4) . ? C17 O3 1.248(4) . ? C17 C18 1.504(4) . ? C18 C19 1.305(5) . ? C18 H18 0.9300 . ? C19 C20 1.480(4) . ? C19 H19 0.9300 . ? C20 O5 1.205(4) . ? C20 O4 1.301(4) . ? N2 H2N 1.04(6) . ? O4 H4 0.90(7) . ? O6A O6B 1.006(14) . ? 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 2.1(5) . . . . ? C7 C1 C2 C3 -175.6(3) . . . . ? C6 C1 C2 Cl1 -177.1(2) . . . . ? C7 C1 C2 Cl1 5.2(4) . . . . ? C1 C2 C3 C4 -0.9(5) . . . . ? Cl1 C2 C3 C4 178.3(3) . . . . ? C2 C3 C4 C5 -1.1(5) . . . . ? C2 C3 C4 Cl2 179.7(2) . . . . ? C3 C4 C5 C6 1.8(6) . . . . ? Cl2 C4 C5 C6 -179.1(3) . . . . ? C2 C1 C6 C5 -1.4(5) . . . . ? C7 C1 C6 C5 176.3(3) . . . . ? C4 C5 C6 C1 -0.5(6) . . . . ? C6 C1 C7 O1 24.3(4) . . . . ? C2 C1 C7 O1 -158.1(3) . . . . ? C6 C1 C7 C8 -94.4(4) . . . . ? C2 C1 C7 C8 83.2(4) . . . . ? O1 C7 C8 N1 71.4(3) . . . . ? C1 C7 C8 N1 -167.1(3) . . . . ? N2 C10 C11 N1 0.7(4) . . . . ? S1 C13 C14 C15 0.8(4) . . . . ? Cl3 C13 C14 C15 -178.2(3) . . . . ? S1 C13 C14 C12 -179.5(2) . . . . ? Cl3 C13 C14 C12 1.4(5) . . . . ? O1 C12 C14 C13 -110.5(4) . . . . ? O1 C12 C14 C15 69.0(4) . . . . ? C13 C14 C15 C16 -0.5(4) . . . . ? C12 C14 C15 C16 179.8(3) . . . . ? C14 C15 C16 S1 0.0(4) . . . . ? O2 C17 C18 C19 -170.0(4) . . . . ? O3 C17 C18 C19 9.3(6) . . . . ? C17 C18 C19 C20 176.7(3) . . . . ? C18 C19 C20 O5 177.4(4) . . . . ? C18 C19 C20 O4 -2.0(6) . . . . ? N2 C9 N1 C11 0.4(4) . . . . ? N2 C9 N1 C8 176.7(3) . . . . ? C10 C11 N1 C9 -0.7(4) . . . . ? C10 C11 N1 C8 -177.0(3) . . . . ? C7 C8 N1 C9 -100.4(4) . . . . ? C7 C8 N1 C11 75.2(4) . . . . ? N1 C9 N2 C10 0.0(4) . . . . ? C11 C10 N2 C9 -0.4(4) . . . . ? C8 C7 O1 C12 -144.8(3) . . . . ? C1 C7 O1 C12 95.5(3) . . . . ? C14 C12 O1 C7 73.9(3) . . . . ? C15 C16 S1 C13 0.4(3) . . . . ? C14 C13 S1 C16 -0.7(3) . . . . ? Cl3 C13 S1 C16 178.4(2) . . . . ?