#------------------------------------------------------------------------------ #$Date: 2023-11-15 01:36:00 +0200 (Wed, 15 Nov 2023) $ #$Revision: 287595 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247710.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_7247710 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 Multi-component Crystals of the Antifungal Drug Tioconazole and the Assessment of their Biopharmaceutical Attributes ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D3CE00948C _journal_year 2023 _chemical_formula_moiety 'C16 H13 Cl3 N2 O S, C7 H3 Cl N O4' _chemical_formula_sum 'C23 H16 Cl4 N3 O5 S' _chemical_formula_weight 588.25 _chemical_name_common 'Tiaconazole-2-Chloro-4-nitrobenzoic acid cocrystal' _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 _audit_creation_method SHELXL-2019/2 _audit_update_record ; 2023-07-31 deposited with the CCDC. 2023-11-14 downloaded from the CCDC. ; _cell_angle_alpha 110.029(5) _cell_angle_beta 96.939(5) _cell_angle_gamma 103.891(5) _cell_formula_units_Z 2 _cell_length_a 7.7627(5) _cell_length_b 11.9414(6) _cell_length_c 14.9934(7) _cell_measurement_reflns_used 3939 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 30.4050 _cell_measurement_theta_min 2.8410 _cell_volume 1235.79(13) _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-2019/2 (Sheldrick, 2019)' _computing_structure_solution 'SHELXT-2018/2 (Sheldrick, 2015)' _diffrn_ambient_temperature 100(2) _diffrn_detector CCD _diffrn_detector_area_resol_mean 28.5714 _diffrn_measured_fraction_theta_full 0.861 _diffrn_measured_fraction_theta_max 0.731 _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 -30.00 70.00 0.50 10.00 -- -20.00 60.00 0.00 200 2 \w -30.00 70.00 0.50 10.00 -- -20.00 60.00 90.00 200 3 \w -110.00 -10.00 0.50 10.00 -- -20.00 -60.00 180.00 200 4 \w -110.00 -10.00 0.50 10.00 -- -20.00 -60.00 180.00 200 ; _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_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0177153000 _diffrn_orient_matrix_UB_12 -0.0095829000 _diffrn_orient_matrix_UB_13 -0.0500157000 _diffrn_orient_matrix_UB_21 -0.0237310000 _diffrn_orient_matrix_UB_22 -0.0655797000 _diffrn_orient_matrix_UB_23 -0.0128564000 _diffrn_orient_matrix_UB_31 -0.0918952000 _diffrn_orient_matrix_UB_32 -0.0022438000 _diffrn_orient_matrix_UB_33 0.0008814000 _diffrn_radiation_monochromator Confocal _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1408 _diffrn_reflns_av_unetI/netI 0.1240 _diffrn_reflns_Laue_measured_fraction_full 0.861 _diffrn_reflns_Laue_measured_fraction_max 0.731 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 12445 _diffrn_reflns_point_group_measured_fraction_full 0.861 _diffrn_reflns_point_group_measured_fraction_max 0.731 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 31.400 _diffrn_reflns_theta_min 1.483 _diffrn_source MicroMax003_Mo _exptl_absorpt_coefficient_mu 0.605 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.33594 _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 1.581 _exptl_crystal_description plate _exptl_crystal_F_000 598 _exptl_crystal_size_max 0.270 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.090 _refine_diff_density_max 0.593 _refine_diff_density_min -0.883 _refine_diff_density_rms 0.145 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 334 _refine_ls_number_reflns 5965 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.047 _refine_ls_R_factor_all 0.1344 _refine_ls_R_factor_gt 0.0874 _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^)+(0.1343P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2182 _refine_ls_wR_factor_ref 0.2393 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3665 _reflns_number_total 5965 _reflns_threshold_expression 'I > 2\s(I)' _twin_special_details ; Component 2 rotated by 10.7356\% around [-0.90 0.44 -0.03] (reciprocal) or [-1.00 0.02 -0.07] (direct) ; _cod_data_source_file d3ce00948c2.cif _cod_data_source_block TCZ-CNBA _cod_database_code 7247710 _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 0.854 _shelx_estimated_absorpt_t_max 0.948 _oxdiff_exptl_absorpt_empirical_full_min 0.504 _oxdiff_exptl_absorpt_empirical_full_max 2.303 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_twin_items 2 _oxdiff_twin_integration_method simultaneous _shelx_res_file ; TITL shelxt_a.res in P-1 shelx.res created by SHELXL-2019/2 at 14:09:30 on 31-Jul-2023 CELL 0.71073 7.7627 11.9414 14.9934 110.029 96.939 103.891 ZERR 2.00 0.0005 0.0006 0.0007 0.005 0.005 0.005 LATT 1 SFAC C H N O S CL UNIT 46 32 6 10 2 8 MERG 2 OMIT 0 -9 20 OMIT 0 1 1 OMIT 0 1 0 FMAP 2 PLAN 2 SIZE 0.090 0.120 0.270 ACTA BOND $H CONF LIST 6 L.S. 10 TEMP -173.00 WGHT 0.134300 FVAR 2.05100 0.93785 C1 1 0.824430 0.613546 0.783252 11.00000 0.01044 0.02408 = 0.01951 0.00762 -0.00272 -0.00015 C2 1 0.887057 0.579516 0.858785 11.00000 0.00802 0.03039 = 0.02577 0.01396 -0.00349 0.00088 C3 1 0.909571 0.654768 0.956137 11.00000 0.01640 0.04302 = 0.01456 0.00992 -0.00407 -0.00151 AFIX 43 H3 2 0.948954 0.628395 1.005945 11.00000 -1.20000 AFIX 0 C4 1 0.874595 0.766989 0.979611 11.00000 0.02069 0.03851 = 0.01965 -0.00061 -0.00063 0.00013 C5 1 0.813440 0.806274 0.906601 11.00000 0.01977 0.03391 = 0.03164 0.00668 -0.00376 0.01117 AFIX 43 H5 2 0.789269 0.884325 0.922994 11.00000 -1.20000 AFIX 0 C6 1 0.789098 0.727866 0.809472 11.00000 0.01725 0.02924 = 0.02714 0.01187 0.00054 0.00412 AFIX 43 H6 2 0.747030 0.753454 0.759684 11.00000 -1.20000 AFIX 0 C7 1 0.797059 0.529822 0.677547 11.00000 0.01733 0.02358 = 0.01645 0.00987 -0.00097 0.00326 AFIX 13 H7 2 0.903220 0.496836 0.668162 11.00000 -1.20000 AFIX 0 C8 1 0.620979 0.420519 0.645998 11.00000 0.01539 0.02864 = 0.01612 0.00872 -0.00016 0.00120 AFIX 23 H8A 2 0.610619 0.388230 0.698392 11.00000 -1.20000 H8B 2 0.515040 0.450778 0.635854 11.00000 -1.20000 AFIX 0 C9 1 0.594700 0.318722 0.465427 11.00000 0.02710 0.02612 = 0.01614 0.01095 -0.00521 0.00352 AFIX 43 H9 2 0.573607 0.385283 0.449238 11.00000 -1.20000 AFIX 0 C10 1 0.636245 0.141118 0.453191 11.00000 0.02620 0.02784 = 0.01758 0.01087 -0.00318 0.00731 AFIX 43 H10 2 0.648773 0.059795 0.425976 11.00000 -1.20000 AFIX 0 C11 1 0.645940 0.205903 0.549078 11.00000 0.02463 0.02532 = 0.01803 0.01263 -0.00186 0.00524 AFIX 43 H11 2 0.667544 0.179257 0.601129 11.00000 -1.20000 AFIX 0 C12 1 0.942776 0.669809 0.607740 11.00000 0.01338 0.02689 = 0.03489 0.02003 0.00003 0.00041 AFIX 23 H12A 2 1.027010 0.619868 0.588769 11.00000 -1.20000 H12B 2 1.001525 0.738749 0.671779 11.00000 -1.20000 AFIX 0 C13 1 0.877856 0.835896 0.549666 11.00000 0.01903 0.01972 = 0.01690 0.00440 0.00079 0.00191 C14 1 0.895971 0.721197 0.531944 11.00000 0.01002 0.02036 = 0.02283 0.00808 -0.00224 -0.00254 C15 1 0.868712 0.651836 0.429738 11.00000 0.01323 0.02050 = 0.03059 0.00309 0.00365 0.00049 AFIX 43 H15 2 0.873950 0.568551 0.402617 11.00000 -1.20000 AFIX 0 C16 1 0.834629 0.718151 0.376016 11.00000 0.01767 0.03230 = 0.01757 0.00397 0.00211 -0.00438 AFIX 43 H16 2 0.816483 0.687308 0.307097 11.00000 -1.20000 AFIX 0 C17 1 0.642841 0.254231 0.104643 11.00000 0.01095 0.01826 = 0.01435 0.00622 -0.00357 0.00064 C18 1 0.607846 0.342661 0.068846 11.00000 0.01740 0.02020 = 0.01451 0.00644 -0.00191 0.00236 C19 1 0.582532 0.319035 -0.030517 11.00000 0.02278 0.02241 = 0.01385 0.00772 -0.00737 0.00021 AFIX 43 H19 2 0.554333 0.377530 -0.055130 11.00000 -1.20000 AFIX 0 C20 1 0.600013 0.207070 -0.092082 11.00000 0.01643 0.01973 = 0.01182 0.00278 -0.00118 -0.00254 C21 1 0.639707 0.120168 -0.059229 11.00000 0.02099 0.01882 = 0.01686 0.00549 0.00068 0.00185 AFIX 43 H21 2 0.653537 0.045353 -0.103062 11.00000 -1.20000 AFIX 0 C22 1 0.659177 0.143610 0.038899 11.00000 0.02056 0.02107 = 0.01606 0.00722 -0.00289 0.00189 C23 1 0.655612 0.271171 0.210658 11.00000 0.01936 0.02922 = 0.00770 0.00644 -0.00401 0.00452 N1 3 0.617946 0.318579 0.555488 11.00000 0.01379 0.02557 = 0.01485 0.00921 -0.00048 -0.00051 N2 3 0.605320 0.213372 0.402715 11.00000 0.02033 0.02428 = 0.01743 0.01027 -0.00133 -0.00040 N3 3 0.568020 0.181761 -0.196605 11.00000 0.02228 0.02308 = 0.01636 0.00539 -0.00185 0.00011 O1 4 0.771417 0.591550 0.612527 11.00000 0.01499 0.02396 = 0.02107 0.01314 -0.00312 0.00122 O2 4 0.587085 0.169512 0.222249 11.00000 0.03393 0.02378 = 0.01529 0.00878 -0.00186 -0.00179 O3 4 0.723896 0.375315 0.275965 11.00000 0.04047 0.02403 = 0.01520 0.00345 -0.01078 0.00370 O4 4 0.485830 0.243107 -0.226647 11.00000 0.03100 0.03431 = 0.02183 0.01613 -0.00276 0.01018 O5 4 0.620654 0.099737 -0.249663 11.00000 0.05725 0.03685 = 0.01778 0.01080 0.00741 0.02225 S1 5 0.827817 0.863295 0.445660 11.00000 0.02760 0.02607 = 0.02279 0.01266 -0.00245 0.00165 CL1 6 0.934956 0.437345 0.830282 11.00000 0.02390 0.03495 = 0.02657 0.01700 -0.00238 0.00849 CL2 6 0.902215 0.862112 1.100676 11.00000 0.03411 0.05941 = 0.02399 -0.00551 -0.00147 0.00568 CL3 6 0.892068 0.948648 0.661357 11.00000 0.05197 0.02611 = 0.02022 0.00271 0.00812 0.00477 CL4A 6 0.582853 0.482642 0.142375 21.00000 0.01957 0.01984 = 0.01447 0.00383 -0.00291 0.00677 CL4B 6 0.735939 0.070153 0.079608 -21.00000 0.06424 H2 2 0.604890 0.184161 0.306989 11.00000 0.10841 HKLF 4 REM shelxt_a.res in P-1 REM wR2 = 0.2393, GooF = S = 1.047, Restrained GooF = 1.047 for all data REM R1 = 0.0874 for 3665 Fo > 4sig(Fo) and 0.1344 for all 5965 data REM 334 parameters refined using 0 restraints END WGHT 0.1343 0.0000 REM Highest difference peak 0.593, deepest hole -0.883, 1-sigma level 0.145 Q1 1 0.7871 0.8713 0.6779 11.00000 0.05 0.59 Q2 1 0.6639 0.2426 -0.2217 11.00000 0.05 0.58 ; _shelx_res_checksum 33282 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 0.8244(6) 0.6135(4) 0.7833(3) 0.0198(10) Uani 1 1 d . . . . . C2 C 0.8871(6) 0.5795(5) 0.8588(3) 0.0221(10) Uani 1 1 d . . . . . C3 C 0.9096(6) 0.6548(5) 0.9561(3) 0.0277(12) Uani 1 1 d . . . . . H3 H 0.948954 0.628395 1.005945 0.033 Uiso 1 1 calc R U . . . C4 C 0.8746(7) 0.7670(5) 0.9796(3) 0.0317(13) Uani 1 1 d . . . . . C5 C 0.8134(7) 0.8063(5) 0.9066(4) 0.0304(12) Uani 1 1 d . . . . . H5 H 0.789269 0.884325 0.922994 0.036 Uiso 1 1 calc R U . . . C6 C 0.7891(7) 0.7279(5) 0.8095(3) 0.0252(11) Uani 1 1 d . . . . . H6 H 0.747030 0.753454 0.759684 0.030 Uiso 1 1 calc R U . . . C7 C 0.7971(6) 0.5298(4) 0.6775(3) 0.0195(10) Uani 1 1 d . . . . . H7 H 0.903220 0.496836 0.668162 0.023 Uiso 1 1 calc R U . . . C8 C 0.6210(6) 0.4205(4) 0.6460(3) 0.0214(10) Uani 1 1 d . . . . . H8A H 0.610619 0.388230 0.698392 0.026 Uiso 1 1 calc R U . . . H8B H 0.515040 0.450778 0.635854 0.026 Uiso 1 1 calc R U . . . C9 C 0.5947(7) 0.3187(4) 0.4654(3) 0.0241(11) Uani 1 1 d . . . . . H9 H 0.573607 0.385283 0.449238 0.029 Uiso 1 1 calc R U . . . C10 C 0.6362(7) 0.1411(5) 0.4532(3) 0.0242(11) Uani 1 1 d . . . . . H10 H 0.648773 0.059795 0.425976 0.029 Uiso 1 1 calc R U . . . C11 C 0.6459(7) 0.2059(4) 0.5491(3) 0.0225(10) Uani 1 1 d . . . . . H11 H 0.667544 0.179257 0.601129 0.027 Uiso 1 1 calc R U . . . C12 C 0.9428(7) 0.6698(5) 0.6077(4) 0.0244(10) Uani 1 1 d . . . . . H12A H 1.027010 0.619868 0.588769 0.029 Uiso 1 1 calc R U . . . H12B H 1.001525 0.738749 0.671779 0.029 Uiso 1 1 calc R U . . . C13 C 0.8779(6) 0.8359(4) 0.5497(3) 0.0203(10) Uani 1 1 d . . . . . C14 C 0.8960(6) 0.7212(4) 0.5319(3) 0.0197(10) Uani 1 1 d . . . . . C15 C 0.8687(6) 0.6518(4) 0.4297(3) 0.0243(11) Uani 1 1 d . . . . . H15 H 0.873950 0.568551 0.402617 0.029 Uiso 1 1 calc R U . . . C16 C 0.8346(7) 0.7182(5) 0.3760(3) 0.0265(12) Uani 1 1 d . . . . . H16 H 0.816483 0.687308 0.307097 0.032 Uiso 1 1 calc R U . . . C17 C 0.6428(6) 0.2542(4) 0.1046(3) 0.0158(9) Uani 1 1 d . . . . . C18 C 0.6078(6) 0.3427(4) 0.0688(3) 0.0186(9) Uani 1 1 d . . . . . C19 C 0.5825(6) 0.3190(4) -0.0305(3) 0.0218(10) Uani 1 1 d . . . . . H19 H 0.554333 0.377530 -0.055130 0.026 Uiso 1 1 calc R U . . . C20 C 0.6000(6) 0.2071(4) -0.0921(3) 0.0188(10) Uani 1 1 d . . . . . C21 C 0.6397(6) 0.1202(4) -0.0592(3) 0.0204(10) Uani 1 1 d . . . . . H21 H 0.653537 0.045353 -0.103062 0.024 Uiso 1 1 calc R U . . . C22 C 0.6592(7) 0.1436(4) 0.0389(3) 0.0207(10) Uani 1 1 d . . . . . C23 C 0.6556(6) 0.2712(4) 0.2107(3) 0.0201(10) Uani 1 1 d . . . . . N1 N 0.6179(5) 0.3186(3) 0.5555(2) 0.0192(9) Uani 1 1 d . . . . . N2 N 0.6053(5) 0.2134(4) 0.4027(3) 0.0219(9) Uani 1 1 d . . . . . N3 N 0.5680(6) 0.1818(4) -0.1966(3) 0.0230(9) Uani 1 1 d . . . . . O1 O 0.7714(4) 0.5915(3) 0.6125(2) 0.0203(7) Uani 1 1 d . . . . . O2 O 0.5871(5) 0.1695(3) 0.2222(2) 0.0266(8) Uani 1 1 d . . . . . O3 O 0.7239(5) 0.3753(3) 0.2760(2) 0.0304(9) Uani 1 1 d . . . . . O4 O 0.4858(5) 0.2431(3) -0.2266(2) 0.0283(8) Uani 1 1 d . . . . . O5 O 0.6207(6) 0.0997(3) -0.2497(2) 0.0358(9) Uani 1 1 d . . . . . S1 S 0.82782(18) 0.86329(11) 0.44566(8) 0.0266(3) Uani 1 1 d . . . . . Cl1 Cl 0.93496(17) 0.43735(12) 0.83028(8) 0.0279(3) Uani 1 1 d . . . . . Cl2 Cl 0.9022(2) 0.86211(15) 1.10068(9) 0.0475(5) Uani 1 1 d . . . . . Cl3 Cl 0.8921(2) 0.94865(11) 0.66136(8) 0.0358(4) Uani 1 1 d . . . . . Cl4A Cl 0.58285(16) 0.48264(10) 0.14238(7) 0.0192(3) Uani 0.938(4) 1 d . . P . . Cl4B Cl 0.736(5) 0.070(3) 0.080(2) 0.064(9) Uiso 0.062(4) 1 d . . P . . H2 H 0.605(12) 0.184(8) 0.307(7) 0.11(3) 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 0.010(2) 0.024(2) 0.020(2) 0.0076(17) -0.0027(16) -0.0001(19) C2 0.008(2) 0.030(2) 0.026(2) 0.0140(18) -0.0035(17) 0.0009(19) C3 0.016(3) 0.043(3) 0.015(2) 0.0099(19) -0.0041(17) -0.002(2) C4 0.021(3) 0.039(3) 0.020(2) -0.001(2) -0.0006(19) 0.000(2) C5 0.020(3) 0.034(3) 0.032(3) 0.007(2) -0.004(2) 0.011(2) C6 0.017(3) 0.029(2) 0.027(2) 0.0119(19) 0.0005(19) 0.004(2) C7 0.017(2) 0.024(2) 0.0165(19) 0.0099(16) -0.0010(16) 0.0033(19) C8 0.015(2) 0.029(2) 0.016(2) 0.0087(17) -0.0002(16) 0.001(2) C9 0.027(3) 0.026(2) 0.016(2) 0.0110(17) -0.0052(18) 0.004(2) C10 0.026(3) 0.028(2) 0.018(2) 0.0109(17) -0.0032(18) 0.007(2) C11 0.025(3) 0.025(2) 0.018(2) 0.0126(17) -0.0019(18) 0.005(2) C12 0.013(2) 0.027(2) 0.035(3) 0.020(2) 0.0000(19) 0.000(2) C13 0.019(3) 0.020(2) 0.0169(19) 0.0044(16) 0.0008(17) 0.0019(19) C14 0.010(2) 0.020(2) 0.023(2) 0.0081(16) -0.0022(16) -0.0025(18) C15 0.013(2) 0.021(2) 0.031(2) 0.0031(18) 0.0036(18) 0.0005(19) C16 0.018(3) 0.032(2) 0.018(2) 0.0040(18) 0.0021(18) -0.004(2) C17 0.011(2) 0.0183(19) 0.0144(18) 0.0062(15) -0.0036(15) 0.0006(17) C18 0.017(2) 0.020(2) 0.0145(19) 0.0064(15) -0.0019(16) 0.0024(18) C19 0.023(3) 0.022(2) 0.0139(19) 0.0077(16) -0.0074(17) 0.000(2) C20 0.016(2) 0.020(2) 0.0118(18) 0.0028(15) -0.0012(16) -0.0025(18) C21 0.021(3) 0.019(2) 0.017(2) 0.0055(16) 0.0007(17) 0.0019(19) C22 0.021(3) 0.021(2) 0.0161(19) 0.0072(16) -0.0029(17) 0.0019(19) C23 0.019(3) 0.029(2) 0.0077(17) 0.0064(16) -0.0040(15) 0.005(2) N1 0.014(2) 0.0256(19) 0.0149(16) 0.0092(14) -0.0005(14) -0.0005(16) N2 0.020(2) 0.0243(19) 0.0174(17) 0.0103(14) -0.0013(15) -0.0004(17) N3 0.022(2) 0.0231(19) 0.0164(17) 0.0054(15) -0.0018(15) 0.0001(18) O1 0.0150(17) 0.0240(15) 0.0211(15) 0.0131(12) -0.0031(12) 0.0012(13) O2 0.034(2) 0.0238(16) 0.0153(15) 0.0088(12) -0.0019(13) -0.0018(15) O3 0.040(2) 0.0240(17) 0.0152(15) 0.0035(12) -0.0108(14) 0.0037(16) O4 0.031(2) 0.0343(19) 0.0218(16) 0.0161(14) -0.0028(14) 0.0102(16) O5 0.057(3) 0.037(2) 0.0178(16) 0.0108(15) 0.0074(16) 0.022(2) S1 0.0276(7) 0.0261(6) 0.0228(6) 0.0127(4) -0.0025(5) 0.0017(5) Cl1 0.0239(7) 0.0350(6) 0.0266(6) 0.0170(5) -0.0024(5) 0.0085(5) Cl2 0.0341(9) 0.0594(9) 0.0240(6) -0.0055(6) -0.0015(5) 0.0057(7) Cl3 0.0520(9) 0.0261(6) 0.0202(5) 0.0027(4) 0.0081(5) 0.0048(6) Cl4A 0.0196(7) 0.0198(6) 0.0145(5) 0.0038(4) -0.0029(4) 0.0068(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 117.2(4) . . ? C6 C1 C7 121.3(4) . . ? C2 C1 C7 121.5(5) . . ? C3 C2 C1 121.9(5) . . ? C3 C2 Cl1 118.8(4) . . ? C1 C2 Cl1 119.2(4) . . ? C4 C3 C2 119.5(5) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 120.9(4) . . ? C3 C4 Cl2 120.1(4) . . ? C5 C4 Cl2 119.0(5) . . ? C6 C5 C4 118.4(5) . . ? C6 C5 H5 120.8 . . ? C4 C5 H5 120.8 . . ? C1 C6 C5 122.1(5) . . ? C1 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? O1 C7 C1 112.9(4) . . ? O1 C7 C8 104.2(4) . . ? C1 C7 C8 110.3(3) . . ? O1 C7 H7 109.8 . . ? C1 C7 H7 109.8 . . ? C8 C7 H7 109.8 . . ? N1 C8 C7 111.4(4) . . ? N1 C8 H8A 109.3 . . ? C7 C8 H8A 109.3 . . ? N1 C8 H8B 109.3 . . ? C7 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? N2 C9 N1 110.2(4) . . ? N2 C9 H9 124.9 . . ? N1 C9 H9 124.9 . . ? C11 C10 N2 108.3(4) . . ? C11 C10 H10 125.9 . . ? N2 C10 H10 125.9 . . ? C10 C11 N1 106.2(4) . . ? C10 C11 H11 126.9 . . ? N1 C11 H11 126.9 . . ? O1 C12 C14 106.2(4) . . ? O1 C12 H12A 110.5 . . ? C14 C12 H12A 110.5 . . ? O1 C12 H12B 110.5 . . ? C14 C12 H12B 110.5 . . ? H12A C12 H12B 108.7 . . ? C14 C13 S1 113.2(3) . . ? C14 C13 Cl3 127.0(4) . . ? S1 C13 Cl3 119.7(3) . . ? C13 C14 C15 111.1(4) . . ? C13 C14 C12 126.0(4) . . ? C15 C14 C12 122.8(4) . . ? C16 C15 C14 112.5(4) . . ? C16 C15 H15 123.8 . . ? C14 C15 H15 123.8 . . ? C15 C16 S1 112.6(3) . . ? C15 C16 H16 123.7 . . ? S1 C16 H16 123.7 . . ? C22 C17 C18 118.3(4) . . ? C22 C17 C23 118.8(4) . . ? C18 C17 C23 122.9(4) . . ? C19 C18 C17 121.1(4) . . ? C19 C18 Cl4A 116.0(4) . . ? C17 C18 Cl4A 122.9(3) . . ? C20 C19 C18 117.7(4) . . ? C20 C19 H19 121.1 . . ? C18 C19 H19 121.1 . . ? C21 C20 C19 122.8(4) . . ? C21 C20 N3 120.0(4) . . ? C19 C20 N3 117.2(4) . . ? C20 C21 C22 118.7(4) . . ? C20 C21 H21 120.7 . . ? C22 C21 H21 120.7 . . ? C21 C22 C17 121.4(4) . . ? C21 C22 Cl4B 120.6(13) . . ? C17 C22 Cl4B 116.6(13) . . ? O3 C23 O2 125.9(4) . . ? O3 C23 C17 120.5(4) . . ? O2 C23 C17 113.7(4) . . ? C9 N1 C11 107.5(4) . . ? C9 N1 C8 126.9(4) . . ? C11 N1 C8 125.6(4) . . ? C9 N2 C10 107.8(4) . . ? C9 N2 H2 127(4) . . ? C10 N2 H2 125(4) . . ? O5 N3 O4 123.4(4) . . ? O5 N3 C20 118.5(4) . . ? O4 N3 C20 118.0(4) . . ? C7 O1 C12 112.2(3) . . ? C23 O2 H2 113(4) . . ? C16 S1 C13 90.5(2) . . ? 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 1.390(7) . ? C1 C2 1.400(6) . ? C1 C7 1.513(6) . ? C2 C3 1.390(6) . ? C2 Cl1 1.746(5) . ? C3 C4 1.367(8) . ? C3 H3 0.9500 . ? C4 C5 1.406(8) . ? C4 Cl2 1.734(5) . ? C5 C6 1.396(7) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O1 1.431(5) . ? C7 C8 1.536(6) . ? C7 H7 1.0000 . ? C8 N1 1.473(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N2 1.316(6) . ? C9 N1 1.341(5) . ? C9 H9 0.9500 . ? C10 C11 1.362(6) . ? C10 N2 1.370(6) . ? C10 H10 0.9500 . ? C11 N1 1.387(6) . ? C11 H11 0.9500 . ? C12 O1 1.456(5) . ? C12 C14 1.512(6) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.349(7) . ? C13 S1 1.719(5) . ? C13 Cl3 1.723(4) . ? C14 C15 1.431(6) . ? C15 C16 1.353(7) . ? C15 H15 0.9500 . ? C16 S1 1.707(5) . ? C16 H16 0.9500 . ? C17 C22 1.397(6) . ? C17 C18 1.403(6) . ? C17 C23 1.520(5) . ? C18 C19 1.397(6) . ? C18 Cl4A 1.730(5) . ? C19 C20 1.389(7) . ? C19 H19 0.9500 . ? C20 C21 1.372(7) . ? C20 N3 1.468(5) . ? C21 C22 1.382(6) . ? C21 H21 0.9500 . ? C22 Cl4B 1.42(4) . ? C23 O3 1.229(5) . ? C23 O2 1.282(5) . ? N2 H2 1.36(9) . ? N3 O5 1.223(5) . ? N3 O4 1.236(5) . ? O2 H2 1.21(9) . ? 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 1.4(7) . . . . ? C7 C1 C2 C3 -178.8(4) . . . . ? C6 C1 C2 Cl1 -179.6(3) . . . . ? C7 C1 C2 Cl1 0.1(6) . . . . ? C1 C2 C3 C4 -1.8(7) . . . . ? Cl1 C2 C3 C4 179.3(4) . . . . ? C2 C3 C4 C5 1.0(8) . . . . ? C2 C3 C4 Cl2 -179.9(4) . . . . ? C3 C4 C5 C6 0.1(8) . . . . ? Cl2 C4 C5 C6 -179.0(4) . . . . ? C2 C1 C6 C5 -0.3(7) . . . . ? C7 C1 C6 C5 180.0(4) . . . . ? C4 C5 C6 C1 -0.4(8) . . . . ? C6 C1 C7 O1 12.6(6) . . . . ? C2 C1 C7 O1 -167.2(4) . . . . ? C6 C1 C7 C8 -103.5(5) . . . . ? C2 C1 C7 C8 76.8(6) . . . . ? O1 C7 C8 N1 75.8(5) . . . . ? C1 C7 C8 N1 -162.7(4) . . . . ? N2 C10 C11 N1 0.7(5) . . . . ? S1 C13 C14 C15 0.1(5) . . . . ? Cl3 C13 C14 C15 177.8(3) . . . . ? S1 C13 C14 C12 178.9(4) . . . . ? Cl3 C13 C14 C12 -3.5(8) . . . . ? O1 C12 C14 C13 99.4(5) . . . . ? O1 C12 C14 C15 -82.0(6) . . . . ? C13 C14 C15 C16 1.0(6) . . . . ? C12 C14 C15 C16 -177.8(4) . . . . ? C14 C15 C16 S1 -1.7(5) . . . . ? C22 C17 C18 C19 2.6(7) . . . . ? C23 C17 C18 C19 -174.8(4) . . . . ? C22 C17 C18 Cl4A 179.5(3) . . . . ? C23 C17 C18 Cl4A 2.2(6) . . . . ? C17 C18 C19 C20 -2.4(7) . . . . ? Cl4A C18 C19 C20 -179.5(3) . . . . ? C18 C19 C20 C21 0.3(7) . . . . ? C18 C19 C20 N3 178.3(4) . . . . ? C19 C20 C21 C22 1.5(7) . . . . ? N3 C20 C21 C22 -176.5(4) . . . . ? C20 C21 C22 C17 -1.3(7) . . . . ? C20 C21 C22 Cl4B -167.1(15) . . . . ? C18 C17 C22 C21 -0.7(7) . . . . ? C23 C17 C22 C21 176.7(4) . . . . ? C18 C17 C22 Cl4B 165.7(15) . . . . ? C23 C17 C22 Cl4B -16.9(15) . . . . ? C22 C17 C23 O3 146.4(5) . . . . ? C18 C17 C23 O3 -36.3(7) . . . . ? C22 C17 C23 O2 -34.8(6) . . . . ? C18 C17 C23 O2 142.5(5) . . . . ? N2 C9 N1 C11 0.3(6) . . . . ? N2 C9 N1 C8 178.1(4) . . . . ? C10 C11 N1 C9 -0.6(5) . . . . ? C10 C11 N1 C8 -178.4(4) . . . . ? C7 C8 N1 C9 -72.5(6) . . . . ? C7 C8 N1 C11 104.9(5) . . . . ? N1 C9 N2 C10 0.1(6) . . . . ? C11 C10 N2 C9 -0.5(6) . . . . ? C21 C20 N3 O5 -18.0(6) . . . . ? C19 C20 N3 O5 163.9(4) . . . . ? C21 C20 N3 O4 160.6(4) . . . . ? C19 C20 N3 O4 -17.4(6) . . . . ? C1 C7 O1 C12 80.0(5) . . . . ? C8 C7 O1 C12 -160.3(4) . . . . ? C14 C12 O1 C7 176.2(4) . . . . ? C15 C16 S1 C13 1.5(4) . . . . ? C14 C13 S1 C16 -0.9(4) . . . . ? Cl3 C13 S1 C16 -178.8(3) . . . . ? loop_ _twin_individual_id _twin_individual_mass_fraction_refined _oxdiff_twin_reflns_isolated _oxdiff_twin_reflns_overlapped _twin_individual_twin_lattice_type _twin_individual_twin_matrix_11 _twin_individual_twin_matrix_12 _twin_individual_twin_matrix_13 _twin_individual_twin_matrix_21 _twin_individual_twin_matrix_22 _twin_individual_twin_matrix_23 _twin_individual_twin_matrix_31 _twin_individual_twin_matrix_32 _twin_individual_twin_matrix_33 1 0.6368 9774 3560 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000 1.0000 2 0.3632 9496 3560 nmt 1.0088 0.0184 0.0121 0.0207 1.0532 0.1556 -0.1251 -0.2611 0.9014