#------------------------------------------------------------------------------ #$Date: 2024-01-06 10:01:35 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288801 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247723.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_7247723 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, O4 P' _chemical_formula_sum 'C16 H14 Cl3 N2 O5 P S' _chemical_formula_weight 483.67 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-I 2ya' _space_group_name_H-M_alt 'I 1 2/a 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2019/2 _audit_update_record ; 2023-10-27 deposited with the CCDC. 2023-11-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.792(8) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 17.2992(13) _cell_length_b 6.8054(5) _cell_length_c 34.882(3) _cell_measurement_reflns_used 1692 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 73.9490 _cell_measurement_theta_min 2.5610 _cell_volume 4046.8(6) _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 'SHELXS-2013/1 (Sheldrick, 2015)' _diffrn_ambient_temperature 298(2) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.969 _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 -17.00 24.00 0.50 0.05 -- -47.33 19.00 0.00 82 2 \w -121.00 -35.00 0.50 0.05 -- -47.33 -23.00 51.00 172 3 \w -137.00-112.00 0.50 0.05 -- -91.75 -23.00 51.00 50 4 \w -45.00 -20.00 0.50 0.05 -- -91.75 45.00 -30.00 50 5 \w -26.00 26.00 0.50 0.05 -- -47.33 23.00-143.00 104 6 \w 151.00 176.00 0.50 0.05 -- 113.25 45.00-120.00 50 7 \w 101.00 172.00 0.50 0.05 -- 113.25 23.00-143.00 142 8 \w 103.00 128.00 0.50 0.05 -- 113.25 45.00-120.00 50 9 \w 62.00 103.00 0.50 0.05 -- 47.33 23.00-143.00 82 10 \w 103.00 137.00 0.50 0.05 -- 113.25 45.00 -60.00 68 11 \w 153.00 178.00 0.50 0.05 -- 113.25 45.00 -60.00 50 12 \w 101.00 165.00 0.50 0.05 -- 113.25 45.00 -30.00 128 13 \w 101.00 172.00 0.50 0.05 -- 113.25 15.00 90.00 142 14 \w 102.00 167.00 0.50 0.05 -- 113.25 15.00 150.00 130 15 \w 42.00 103.00 0.50 0.05 -- 113.25 -77.00 0.00 122 16 \w 47.00 73.00 0.50 0.05 -- 113.25 -61.00 90.00 52 17 \w 46.00 73.00 0.50 0.05 -- 113.25 -61.00 150.00 54 18 \w 43.00 73.00 0.50 0.05 -- 113.25 -61.00 30.00 60 19 \w 42.00 67.00 0.50 0.05 -- 113.25 -61.00 -30.00 50 20 \w 48.00 73.00 0.50 0.05 -- 113.25 -61.00 -60.00 50 21 \w 47.00 72.00 0.50 0.05 -- 113.25 -61.00-120.00 50 22 \w 48.00 73.00 0.50 0.05 -- 113.25 -61.00-180.00 50 23 \w -7.00 20.00 0.50 0.05 -- 47.33 -19.00 -60.00 54 24 \w -22.00 3.00 0.50 0.05 -- 47.33 -23.00 51.00 50 25 \w 61.00 105.00 0.50 0.05 -- 113.25 -95.00 -60.00 88 26 \w 44.00 96.00 0.50 0.05 -- 113.25-125.00 0.00 104 27 \w 59.00 99.00 0.50 0.05 -- 113.25 -95.00 0.00 80 28 \w 43.00 90.00 0.50 0.05 -- 47.33-125.00-120.00 94 ; _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 -0.0024557000 _diffrn_orient_matrix_UB_12 0.0472606000 _diffrn_orient_matrix_UB_13 0.0429566000 _diffrn_orient_matrix_UB_21 0.0879570000 _diffrn_orient_matrix_UB_22 -0.0491368000 _diffrn_orient_matrix_UB_23 0.0106418000 _diffrn_orient_matrix_UB_31 0.0204567000 _diffrn_orient_matrix_UB_32 0.2159809000 _diffrn_orient_matrix_UB_33 -0.0069790000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0968 _diffrn_reflns_av_unetI/netI 0.0824 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.969 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_number 14898 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.969 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 80.796 _diffrn_reflns_theta_min 2.571 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 6.105 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.77916 _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 colorless _exptl_crystal_density_diffrn 1.588 _exptl_crystal_description plate _exptl_crystal_F_000 1968 _exptl_crystal_size_max 0.440 _exptl_crystal_size_mid 0.110 _exptl_crystal_size_min 0.020 _refine_diff_density_max 0.511 _refine_diff_density_min -0.420 _refine_diff_density_rms 0.071 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 260 _refine_ls_number_reflns 4311 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.096 _refine_ls_R_factor_all 0.1453 _refine_ls_R_factor_gt 0.0748 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1228P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2161 _refine_ls_wR_factor_ref 0.2693 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2029 _reflns_number_total 4311 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00948c2.cif _cod_data_source_block TCZ-PHOS_AM231023a _cod_depositor_comments 'Adding full bibliography for 7247709--7247724.cif.' _cod_original_cell_volume 4046.7(6) _cod_original_sg_symbol_H-M 'I 2/a' _cod_database_code 7247723 _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 0.174 _shelx_estimated_absorpt_t_max 0.888 _shelx_res_file ; TITL TCZ-PHOS_AM231023a in I2/a shelx.res created by SHELXL-2019/2 at 10:33:47 on 25-Oct-2023 CELL 1.54184 17.2992 6.8054 34.8816 90.000 99.792 90.000 ZERR 8.00 0.0013 0.0005 0.0029 0.000 0.008 0.000 LATT 2 SYMM 1/2 - X, Y, - Z SFAC C H N O CL S P UNIT 128 112 16 40 24 8 8 MERG 2 OMIT -2 8 4 OMIT -2 8 2 FMAP 2 PLAN 2 SIZE 0.020 0.110 0.440 ACTA BOND $H CONF L.S. 10 TEMP 25.00 WGHT 0.122800 FVAR 1.78307 0.90996 0.66421 C1 1 0.418380 0.103303 0.412885 11.00000 0.04811 0.06844 = 0.06183 -0.00014 0.00681 -0.00927 C2 1 0.453538 0.243211 0.438965 11.00000 0.05875 0.07005 = 0.08630 -0.01081 0.00986 -0.01500 C3 1 0.524800 0.210712 0.463054 11.00000 0.06870 0.08806 = 0.08179 -0.01710 -0.00162 -0.01484 AFIX 43 H3 2 0.547722 0.307333 0.480153 11.00000 -1.20000 AFIX 0 C4 1 0.560114 0.034189 0.460980 11.00000 0.05222 0.10921 = 0.05298 -0.00502 0.00351 -0.00749 C5 1 0.528122 -0.109539 0.435496 11.00000 0.07734 0.09170 = 0.08126 -0.01162 -0.00640 0.02045 AFIX 43 H5 2 0.553411 -0.229413 0.434295 11.00000 -1.20000 AFIX 0 C6 1 0.456972 -0.071177 0.411549 11.00000 0.07030 0.08327 = 0.07934 -0.02573 -0.00897 0.00951 AFIX 43 H6 2 0.434931 -0.167190 0.394072 11.00000 -1.20000 AFIX 0 C7 1 0.341848 0.141887 0.385214 11.00000 0.04769 0.06798 = 0.06810 -0.00484 0.00146 -0.00518 AFIX 13 H7 2 0.312393 0.244786 0.396112 11.00000 -1.20000 AFIX 0 C8 1 0.360805 0.210526 0.346505 11.00000 0.05454 0.08535 = 0.07351 0.01259 0.00816 -0.00330 AFIX 23 H8A 2 0.395599 0.323129 0.350673 11.00000 -1.20000 H8B 2 0.387732 0.106423 0.335079 11.00000 -1.20000 AFIX 0 C9 1 0.261884 0.447221 0.313027 11.00000 0.06972 0.08533 = 0.08346 0.00729 0.00400 0.00543 AFIX 43 H9 2 0.285892 0.560767 0.324131 11.00000 -1.20000 AFIX 0 C10 1 0.179015 0.246073 0.278929 11.00000 0.05708 0.10994 = 0.07014 0.00759 0.00419 -0.01002 AFIX 43 H10 2 0.135058 0.198795 0.262405 11.00000 -1.20000 AFIX 0 C11 1 0.237530 0.136815 0.297860 11.00000 0.07617 0.08449 = 0.06519 -0.00103 0.00703 -0.01260 AFIX 43 H11 2 0.242515 0.000993 0.296633 11.00000 -1.20000 AFIX 0 C12 1 0.247954 -0.070105 0.406672 11.00000 0.08164 0.09818 = 0.05803 -0.00466 0.01586 -0.02303 AFIX 23 H12A 2 0.226328 0.050280 0.415334 11.00000 -1.20000 H12B 2 0.279812 -0.132325 0.428943 11.00000 -1.20000 AFIX 0 C13 1 0.166749 -0.379429 0.402623 11.00000 0.07314 0.07934 = 0.07551 -0.00585 0.01563 -0.00686 C14 1 0.183220 -0.204828 0.389178 11.00000 0.06232 0.06440 = 0.06667 -0.00156 0.01275 -0.01132 C15 1 0.129286 -0.161840 0.354455 11.00000 0.07887 0.08583 = 0.07918 0.00674 0.01300 -0.01264 AFIX 43 H15 2 0.129842 -0.045075 0.340653 11.00000 -1.20000 AFIX 0 C16 1 0.077994 -0.306452 0.343844 11.00000 0.06304 0.13182 = 0.07111 -0.00078 0.00463 -0.02430 AFIX 43 H16 2 0.039911 -0.301461 0.321566 11.00000 -1.20000 AFIX 0 CL1B 5 0.411864 0.472361 0.440979 21.00000 0.10202 0.07197 = 0.19595 -0.03737 -0.02165 -0.00114 CL1A 5 0.389173 0.428227 0.455202 -21.00000 0.06469 CL2 5 0.649626 -0.011319 0.490904 11.00000 0.06207 0.16624 = 0.07196 -0.00124 -0.00540 0.00346 CL3 5 0.209165 -0.490464 0.445473 11.00000 0.10626 0.10850 = 0.10172 0.02327 0.00817 0.00170 S1 6 0.088787 -0.497894 0.374509 11.00000 0.08631 0.08990 = 0.09724 -0.01205 0.02219 -0.02949 N1 3 0.288899 0.264799 0.319505 11.00000 0.05655 0.07889 = 0.06460 0.00659 0.00713 -0.00200 N2 3 0.194728 0.439441 0.287976 11.00000 0.06956 0.11528 = 0.08242 0.01538 0.00255 0.02064 O1 4 0.294486 -0.027531 0.377788 11.00000 0.05501 0.07490 = 0.06227 -0.00468 0.00764 -0.01164 O2 4 0.132213 0.762512 0.246575 11.00000 0.07219 0.13463 = 0.14810 0.03917 -0.01999 0.00694 O3A 4 0.033784 0.562879 0.213284 31.00000 0.10210 O3B 4 0.004802 0.628121 0.206823 -31.00000 0.09268 O4A 4 0.003641 0.885299 0.233372 31.00000 0.10369 O4B 4 0.033595 0.968344 0.223745 -31.00000 0.14805 O5A 4 0.073321 0.860336 0.181738 31.00000 0.10427 O5B 4 0.093531 0.782448 0.178679 -31.00000 0.09918 P1 7 0.065267 0.785657 0.218412 11.00000 0.06229 0.06930 = 0.07650 0.00191 0.00421 0.00721 H2N 2 0.166905 0.557178 0.279393 11.00000 0.13701 HKLF 4 REM TCZ-PHOS_AM231023a in I2/a REM wR2 = 0.2693, GooF = S = 1.096, Restrained GooF = 1.096 for all data REM R1 = 0.0748 for 2029 Fo > 4sig(Fo) and 0.1453 for all 4311 data REM 260 parameters refined using 0 restraints END WGHT 0.1189 3.3992 REM Highest difference peak 0.511, deepest hole -0.420, 1-sigma level 0.071 Q1 1 -0.0092 0.7020 0.2205 11.00000 0.05 0.51 Q2 1 0.0678 0.9678 0.1973 11.00000 0.05 0.49 ; _shelx_res_checksum 29891 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4184(3) 0.1033(8) 0.41289(14) 0.0598(12) Uani 1 1 d . . . . . C2 C 0.4535(3) 0.2432(9) 0.43897(18) 0.0720(15) Uani 1 1 d . . . . . C3 C 0.5248(3) 0.2107(10) 0.46305(18) 0.0812(17) Uani 1 1 d . . . . . H3 H 0.547722 0.307333 0.480153 0.097 Uiso 1 1 calc R U . . . C4 C 0.5601(3) 0.0342(10) 0.46098(16) 0.0721(16) Uani 1 1 d . . . . . C5 C 0.5281(3) -0.1095(10) 0.43550(18) 0.0858(18) Uani 1 1 d . . . . . H5 H 0.553411 -0.229413 0.434295 0.103 Uiso 1 1 calc R U . . . C6 C 0.4570(3) -0.0712(10) 0.41155(18) 0.0802(17) Uani 1 1 d . . . . . H6 H 0.434931 -0.167190 0.394072 0.096 Uiso 1 1 calc R U . . . C7 C 0.3418(3) 0.1419(8) 0.38521(15) 0.0622(13) Uani 1 1 d . . . . . H7 H 0.312393 0.244786 0.396112 0.075 Uiso 1 1 calc R U . . . C8 C 0.3608(3) 0.2105(9) 0.34650(16) 0.0714(15) Uani 1 1 d . . . . . H8A H 0.395599 0.323129 0.350673 0.086 Uiso 1 1 calc R U . . . H8B H 0.387732 0.106423 0.335079 0.086 Uiso 1 1 calc R U . . . C9 C 0.2619(3) 0.4472(10) 0.31303(18) 0.0806(17) Uani 1 1 d . . . . . H9 H 0.285892 0.560767 0.324131 0.097 Uiso 1 1 calc R U . . . C10 C 0.1790(3) 0.2461(11) 0.27893(17) 0.0798(17) Uani 1 1 d . . . . . H10 H 0.135058 0.198795 0.262405 0.096 Uiso 1 1 calc R U . . . C11 C 0.2375(3) 0.1368(10) 0.29786(16) 0.0759(16) Uani 1 1 d . . . . . H11 H 0.242515 0.000993 0.296633 0.091 Uiso 1 1 calc R U . . . C12 C 0.2480(3) -0.0701(10) 0.40667(16) 0.0788(16) Uani 1 1 d . . . . . H12A H 0.226328 0.050280 0.415334 0.095 Uiso 1 1 calc R U . . . H12B H 0.279812 -0.132325 0.428943 0.095 Uiso 1 1 calc R U . . . C13 C 0.1667(3) -0.3794(9) 0.40262(17) 0.0756(15) Uani 1 1 d . . . . . C14 C 0.1832(3) -0.2048(8) 0.38918(15) 0.0643(13) Uani 1 1 d . . . . . C15 C 0.1293(3) -0.1618(9) 0.35446(18) 0.0813(16) Uani 1 1 d . . . . . H15 H 0.129842 -0.045075 0.340653 0.098 Uiso 1 1 calc R U . . . C16 C 0.0780(3) -0.3065(11) 0.34384(18) 0.089(2) Uani 1 1 d . . . . . H16 H 0.039911 -0.301461 0.321566 0.107 Uiso 1 1 calc R U . . . Cl1B Cl 0.4119(3) 0.4724(6) 0.4410(3) 0.129(3) Uani 0.91(2) 1 d . . P . . Cl1A Cl 0.3892(18) 0.428(5) 0.4552(5) 0.065(9) Uiso 0.09(2) 1 d . . P . . Cl2 Cl 0.64963(9) -0.0113(3) 0.49090(5) 0.1021(7) Uani 1 1 d . . . . . Cl3 Cl 0.20917(12) -0.4905(3) 0.44547(6) 0.1066(7) Uani 1 1 d . . . . . S1 S 0.08879(10) -0.4979(3) 0.37451(5) 0.0904(6) Uani 1 1 d . . . . . N1 N 0.2889(2) 0.2648(7) 0.31950(13) 0.0670(11) Uani 1 1 d . . . . . N2 N 0.1947(3) 0.4394(11) 0.28798(16) 0.0903(17) Uani 1 1 d . . . . . O1 O 0.29449(19) -0.0275(5) 0.37779(10) 0.0643(9) Uani 1 1 d . . . . . O2 O 0.1322(3) 0.7625(8) 0.24657(17) 0.1228(19) Uani 1 1 d . . . . . O3A O 0.0338(6) 0.5629(16) 0.2133(3) 0.102(3) Uiso 0.66(2) 1 d . . P . . O3B O 0.0048(11) 0.628(3) 0.2068(5) 0.093(6) Uiso 0.34(2) 1 d . . P . . O4A O 0.0036(5) 0.8853(15) 0.2334(2) 0.104(4) Uiso 0.66(2) 1 d . . P . . O4B O 0.0336(15) 0.968(4) 0.2237(7) 0.148(9) Uiso 0.34(2) 1 d . . P . . O5A O 0.0733(6) 0.8603(18) 0.1817(3) 0.104(3) Uiso 0.66(2) 1 d . . P . . O5B O 0.0935(11) 0.782(3) 0.1787(5) 0.099(6) Uiso 0.34(2) 1 d . . P . . P1 P 0.06527(8) 0.7857(2) 0.21841(5) 0.0703(5) Uani 1 1 d . . . . . H2N H 0.167(5) 0.557(12) 0.279(2) 0.14(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 0.048(2) 0.068(3) 0.062(3) 0.000(2) 0.007(2) -0.009(2) C2 0.059(3) 0.070(4) 0.086(4) -0.011(3) 0.010(3) -0.015(3) C3 0.069(3) 0.088(4) 0.082(4) -0.017(3) -0.002(3) -0.015(3) C4 0.052(3) 0.109(5) 0.053(3) -0.005(3) 0.004(2) -0.007(3) C5 0.077(4) 0.092(5) 0.081(4) -0.012(3) -0.006(3) 0.020(3) C6 0.070(3) 0.083(4) 0.079(4) -0.026(3) -0.009(3) 0.010(3) C7 0.048(2) 0.068(3) 0.068(3) -0.005(3) 0.001(2) -0.005(2) C8 0.055(3) 0.085(4) 0.074(3) 0.013(3) 0.008(2) -0.003(3) C9 0.070(3) 0.085(4) 0.083(4) 0.007(3) 0.004(3) 0.005(3) C10 0.057(3) 0.110(5) 0.070(4) 0.008(4) 0.004(3) -0.010(3) C11 0.076(3) 0.084(4) 0.065(3) -0.001(3) 0.007(3) -0.013(3) C12 0.082(4) 0.098(4) 0.058(3) -0.005(3) 0.016(3) -0.023(3) C13 0.073(3) 0.079(4) 0.076(4) -0.006(3) 0.016(3) -0.007(3) C14 0.062(3) 0.064(3) 0.067(3) -0.002(3) 0.013(2) -0.011(3) C15 0.079(4) 0.086(4) 0.079(4) 0.007(3) 0.013(3) -0.013(3) C16 0.063(3) 0.132(6) 0.071(4) -0.001(4) 0.005(3) -0.024(4) Cl1B 0.102(2) 0.0720(16) 0.196(6) -0.037(2) -0.022(3) -0.0011(14) Cl2 0.0621(8) 0.1662(19) 0.0720(9) -0.0012(10) -0.0054(7) 0.0035(9) Cl3 0.1063(13) 0.1085(15) 0.1017(13) 0.0233(10) 0.0082(10) 0.0017(10) S1 0.0863(10) 0.0899(12) 0.0972(12) -0.0120(9) 0.0222(9) -0.0295(8) N1 0.057(2) 0.079(3) 0.065(3) 0.007(2) 0.0071(19) -0.002(2) N2 0.070(3) 0.115(5) 0.082(4) 0.015(3) 0.003(3) 0.021(3) O1 0.0550(18) 0.075(2) 0.062(2) -0.0047(17) 0.0076(15) -0.0116(16) O2 0.072(3) 0.135(4) 0.148(5) 0.039(4) -0.020(3) 0.007(3) P1 0.0623(8) 0.0693(10) 0.0765(9) 0.0019(7) 0.0042(6) 0.0072(7) 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' P P 0.2955 0.4335 '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(5) . . ? C6 C1 C7 120.3(5) . . ? C2 C1 C7 122.4(5) . . ? C1 C2 C3 122.3(6) . . ? C1 C2 Cl1B 120.6(4) . . ? C3 C2 Cl1B 117.0(5) . . ? C1 C2 Cl1A 117.0(12) . . ? C3 C2 Cl1A 116.5(10) . . ? Cl1B C2 Cl1A 24.0(7) . . ? C4 C3 C2 118.1(5) . . ? C4 C3 H3 120.9 . . ? C2 C3 H3 120.9 . . ? C3 C4 C5 122.0(5) . . ? C3 C4 Cl2 119.2(5) . . ? C5 C4 Cl2 118.7(5) . . ? C4 C5 C6 118.3(6) . . ? C4 C5 H5 120.9 . . ? C6 C5 H5 120.9 . . ? C1 C6 C5 122.0(6) . . ? C1 C6 H6 119.0 . . ? C5 C6 H6 119.0 . . ? O1 C7 C8 107.1(4) . . ? O1 C7 C1 113.0(4) . . ? C8 C7 C1 108.7(4) . . ? O1 C7 H7 109.3 . . ? C8 C7 H7 109.3 . . ? C1 C7 H7 109.3 . . ? N1 C8 C7 111.1(4) . . ? 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 . . ? N1 C9 N2 108.4(6) . . ? N1 C9 H9 125.8 . . ? N2 C9 H9 125.8 . . ? C11 C10 N2 108.5(5) . . ? C11 C10 H10 125.8 . . ? N2 C10 H10 125.8 . . ? C10 C11 N1 106.5(6) . . ? C10 C11 H11 126.8 . . ? N1 C11 H11 126.8 . . ? O1 C12 C14 108.1(4) . . ? O1 C12 H12A 110.1 . . ? C14 C12 H12A 110.1 . . ? O1 C12 H12B 110.1 . . ? C14 C12 H12B 110.1 . . ? H12A C12 H12B 108.4 . . ? C14 C13 Cl3 127.9(5) . . ? C14 C13 S1 114.3(5) . . ? Cl3 C13 S1 117.7(4) . . ? C13 C14 C15 109.6(5) . . ? C13 C14 C12 126.6(5) . . ? C15 C14 C12 123.8(5) . . ? C16 C15 C14 113.1(6) . . ? C16 C15 H15 123.5 . . ? C14 C15 H15 123.5 . . ? C15 C16 S1 113.6(5) . . ? C15 C16 H16 123.2 . . ? S1 C16 H16 123.2 . . ? Cl1A Cl1B C2 86.2(18) . . ? Cl1B Cl1A C2 69.8(16) . . ? C16 S1 C13 89.5(3) . . ? C9 N1 C11 108.8(5) . . ? C9 N1 C8 125.1(5) . . ? C11 N1 C8 126.1(5) . . ? C9 N2 C10 107.8(6) . . ? C9 N2 H2N 121(5) . . ? C10 N2 H2N 132(5) . . ? C7 O1 C12 114.6(4) . . ? O3B O3A P1 68.8(16) . . ? O3A O3B P1 86.4(18) . . ? O4B O4A P1 68.8(17) . . ? O4A O4B P1 75(2) . . ? O5B O5A P1 90(2) . . ? O5A O5B P1 65.3(19) . . ? O4B P1 O2 107.9(9) . . ? O4B P1 O5A 84.3(11) . . ? O2 P1 O5A 118.9(4) . . ? O4B P1 O4A 36.0(11) . . ? O2 P1 O4A 112.1(4) . . ? O5A P1 O4A 110.8(5) . . ? O4B P1 O3B 113.8(11) . . ? O2 P1 O3B 124.4(9) . . ? O5A P1 O3B 100.7(8) . . ? O4A P1 O3B 84.8(7) . . ? O4B P1 O5B 109.0(12) . . ? O2 P1 O5B 106.2(7) . . ? O5A P1 O5B 25.0(7) . . ? O4A P1 O5B 134.5(8) . . ? O3B P1 O5B 93.5(8) . . ? O4B P1 O3A 136.6(12) . . ? O2 P1 O3A 101.3(5) . . ? O5A P1 O3A 108.9(6) . . ? O4A P1 O3A 103.1(5) . . ? O3B P1 O3A 24.9(7) . . ? O5B P1 O3A 92.3(8) . . ? 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 1.367(8) . ? C1 C2 1.384(7) . ? C1 C7 1.523(6) . ? C2 C3 1.386(7) . ? C2 Cl1B 1.724(6) . ? C2 Cl1A 1.83(2) . ? C3 C4 1.355(8) . ? C3 H3 0.9300 . ? C4 C5 1.373(8) . ? C4 Cl2 1.742(5) . ? C5 C6 1.390(7) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O1 1.413(6) . ? C7 C8 1.516(7) . ? C7 H7 0.9800 . ? C8 N1 1.474(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N1 1.332(7) . ? C9 N2 1.331(7) . ? C9 H9 0.9300 . ? C10 C11 1.336(8) . ? C10 N2 1.370(8) . ? C10 H10 0.9300 . ? C11 N1 1.375(7) . ? C11 H11 0.9300 . ? C12 O1 1.422(6) . ? C12 C14 1.495(7) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.326(8) . ? C13 Cl3 1.723(6) . ? C13 S1 1.726(6) . ? C14 C15 1.428(8) . ? C15 C16 1.335(8) . ? C15 H15 0.9300 . ? C16 S1 1.676(7) . ? C16 H16 0.9300 . ? Cl1B Cl1A 0.75(2) . ? N2 H2N 0.96(8) . ? O2 P1 1.394(4) . ? O3A O3B 0.679(17) . ? O3A P1 1.611(9) . ? O3B P1 1.504(15) . ? O4A O4B 0.87(3) . ? O4A P1 1.435(8) . ? O4B P1 1.38(2) . ? O5A O5B 0.654(19) . ? O5A P1 1.405(9) . ? O5B P1 1.546(18) . ? 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(9) . . . . ? C7 C1 C2 C3 -177.4(5) . . . . ? C6 C1 C2 Cl1B 176.6(7) . . . . ? C7 C1 C2 Cl1B -0.6(9) . . . . ? C6 C1 C2 Cl1A -156.3(11) . . . . ? C7 C1 C2 Cl1A 26.5(12) . . . . ? C1 C2 C3 C4 -0.8(9) . . . . ? Cl1B C2 C3 C4 -177.7(7) . . . . ? Cl1A C2 C3 C4 155.5(13) . . . . ? C2 C3 C4 C5 1.2(9) . . . . ? C2 C3 C4 Cl2 -179.9(4) . . . . ? C3 C4 C5 C6 -0.6(10) . . . . ? Cl2 C4 C5 C6 -179.5(5) . . . . ? C2 C1 C6 C5 0.7(9) . . . . ? C7 C1 C6 C5 178.0(6) . . . . ? C4 C5 C6 C1 -0.4(10) . . . . ? C6 C1 C7 O1 36.2(7) . . . . ? C2 C1 C7 O1 -146.6(5) . . . . ? C6 C1 C7 C8 -82.6(6) . . . . ? C2 C1 C7 C8 94.6(6) . . . . ? O1 C7 C8 N1 62.0(6) . . . . ? C1 C7 C8 N1 -175.6(4) . . . . ? N2 C10 C11 N1 1.4(7) . . . . ? Cl3 C13 C14 C15 -174.5(5) . . . . ? S1 C13 C14 C15 0.9(6) . . . . ? Cl3 C13 C14 C12 5.8(9) . . . . ? S1 C13 C14 C12 -178.8(5) . . . . ? O1 C12 C14 C13 124.2(6) . . . . ? O1 C12 C14 C15 -55.4(8) . . . . ? C13 C14 C15 C16 -1.4(8) . . . . ? C12 C14 C15 C16 178.2(5) . . . . ? C14 C15 C16 S1 1.4(7) . . . . ? C1 C2 Cl1B Cl1A 88(3) . . . . ? C3 C2 Cl1B Cl1A -95(2) . . . . ? C1 C2 Cl1A Cl1B -105(3) . . . . ? C3 C2 Cl1A Cl1B 97(2) . . . . ? C15 C16 S1 C13 -0.7(5) . . . . ? C14 C13 S1 C16 -0.1(5) . . . . ? Cl3 C13 S1 C16 175.8(4) . . . . ? N2 C9 N1 C11 0.2(7) . . . . ? N2 C9 N1 C8 -178.0(5) . . . . ? C10 C11 N1 C9 -1.0(6) . . . . ? C10 C11 N1 C8 177.2(5) . . . . ? C7 C8 N1 C9 98.2(6) . . . . ? C7 C8 N1 C11 -79.7(7) . . . . ? N1 C9 N2 C10 0.7(7) . . . . ? C11 C10 N2 C9 -1.3(7) . . . . ? C8 C7 O1 C12 -157.9(4) . . . . ? C1 C7 O1 C12 82.4(5) . . . . ? C14 C12 O1 C7 161.0(4) . . . . ? O4A O4B P1 O2 -103.3(15) . . . . ? O4A O4B P1 O5A 138.2(16) . . . . ? O4A O4B P1 O3B 39(2) . . . . ? O4A O4B P1 O5B 141.9(15) . . . . ? O4A O4B P1 O3A 27(3) . . . . ? O5B O5A P1 O4B 172(2) . . . . ? O5B O5A P1 O2 64.5(19) . . . . ? O5B O5A P1 O4A -163.4(18) . . . . ? O5B O5A P1 O3B -75(2) . . . . ? O5B O5A P1 O3A -50.7(19) . . . . ? O4B O4A P1 O2 90.2(17) . . . . ? O4B O4A P1 O5A -45.2(18) . . . . ? O4B O4A P1 O3B -144.6(19) . . . . ? O4B O4A P1 O5B -55(2) . . . . ? O4B O4A P1 O3A -161.5(17) . . . . ? O3A O3B P1 O4B -160(2) . . . . ? O3A O3B P1 O2 -24(2) . . . . ? O3A O3B P1 O5A 112.1(17) . . . . ? O3A O3B P1 O4A -137.7(18) . . . . ? O3A O3B P1 O5B 87.9(19) . . . . ? O5A O5B P1 O4B -9(2) . . . . ? O5A O5B P1 O2 -124.6(17) . . . . ? O5A O5B P1 O4A 22(2) . . . . ? O5A O5B P1 O3B 108(2) . . . . ? O5A O5B P1 O3A 132.9(18) . . . . ? O3B O3A P1 O4B 28(3) . . . . ? O3B O3A P1 O2 159.7(17) . . . . ? O3B O3A P1 O5A -74.2(18) . . . . ? O3B O3A P1 O4A 43.5(18) . . . . ? O3B O3A P1 O5B -93.3(19) . . . . ?