#------------------------------------------------------------------------------ #$Date: 2026-10-02 23:14:58 +0200 (Fri, 02 Oct 2026) $ #$Revision: 306942 $ #$URL: svn://www.crystallography.net/cod/cif/2/02/35/2023590.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2023590 loop_ _publ_author_name 'Kumar, Sharatha' 'H\"okelek, Tuncer' _publ_section_title ; Synthesis, structure and computational study of 1-acetyl-3-(3,5-dichlorophenyl)thiourea ; _journal_coeditor_code WM5812 _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E Crystallographic Communications' _journal_paper_doi 10.1107/S2056989026010121 _journal_volume 82 _journal_year 2026 _chemical_formula_iupac 'C9 H8 Cl2 N2 O S' _chemical_formula_moiety 'C9 H8 Cl2 N2 O S' _chemical_formula_sum 'C9 H8 Cl2 N2 O S' _chemical_formula_weight 263.13 _chemical_name_systematic ; 1-Acetyl-3-(3,5-dichlorophenyl)thiourea ; _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-2018/3 _cell_angle_alpha 102.870(10) _cell_angle_beta 92.650(10) _cell_angle_gamma 99.040(10) _cell_formula_units_Z 2 _cell_length_a 4.5764(9) _cell_length_b 10.873(2) _cell_length_c 12.093(2) _cell_measurement_reflns_used 1807 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.57 _cell_measurement_theta_min 2.90 _cell_volume 577.27(19) _computing_cell_refinement ; CrysAlis RED (Oxford Diffraction, 2009) ; _computing_data_collection ; CrysAlis CCD (Oxford Diffraction, 2009) ; _computing_data_reduction ; CrysAlis RED (Oxford Diffraction, 2009) ; _computing_molecular_graphics ; ORTEP-3 for Windows (Farrugia, 2012) ; _computing_publication_material ; WinGX (Farrugia, 2012) and PLATON (Spek, 2009) ; _computing_structure_refinement ; SHELXL (Sheldrick, 2015b) ; _computing_structure_solution ; SHELXT (Sheldrick, 2015a) ; _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.960 _diffrn_measured_fraction_theta_max 0.960 _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur with Sapphire CCD ; _diffrn_measurement_method ; Rotation method data acquisition using omega scans. ; _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0131 _diffrn_reflns_av_unetI/netI 0.0179 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 3301 _diffrn_reflns_theta_full 25.184 _diffrn_reflns_theta_max 25.184 _diffrn_reflns_theta_min 2.896 _exptl_absorpt_coefficient_mu 0.717 _exptl_absorpt_correction_T_max 0.9318 _exptl_absorpt_correction_T_min 0.7248 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysAlisRED; Oxford Diffraction, 2009) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.514 _exptl_crystal_description needle _exptl_crystal_F_000 268 _exptl_crystal_size_max 0.480 _exptl_crystal_size_mid 0.140 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.461 _refine_diff_density_min -0.398 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.327 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 144 _refine_ls_number_reflns 2007 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.327 _refine_ls_R_factor_all 0.0779 _refine_ls_R_factor_gt 0.0648 _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^)+(0.0189P)^2^+1.3739P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1305 _refine_ls_wR_factor_ref 0.1391 _reflns_number_gt 1747 _reflns_number_total 2007 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file wm5812.cif _cod_data_source_block I _cod_original_cell_volume 577.27(18) _cod_database_code 2023590 _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 0.725 _shelx_estimated_absorpt_t_max 0.932 _shelx_hkl_file ; 0 0 2 2000.83 13.6066 3 0 0 -3 4.45154 3.90353 2 0 0 3 9.44147 7.29739 3 0 0 -3 17.4892 6.04162 1 0 0 3 9.52780 8.69335 0 0 0 -4 12604.5 32.2409 2 0 0 -4 12712.3 42.5868 1 0 0 4 12654.9 47.2282 3 0 0 4 12882.8 50.9323 0 0 0 -5 1349.54 12.2997 2 0 0 5 1309.62 19.9779 0 0 0 -5 1377.24 17.1449 1 0 0 -6 534.276 13.6743 1 0 0 -6 557.628 9.33969 2 0 0 6 534.989 15.1905 0 0 0 -7 1889.95 17.1716 2 0 0 7 1843.53 26.5558 0 0 0 -7 1908.12 24.2962 1 0 0 8 698.683 19.6640 0 0 0 -8 695.277 17.3347 1 0 0 -9 2761.08 32.4469 1 0 0 9 2807.77 37.6869 0 0 0 10 7506.09 62.9265 0 0 0 11 65.9150 12.8843 0 0 0 12 1465.64 32.7613 0 0 0 14 895.281 27.3055 0 0 -1 14 56.9804 12.0226 0 0 -1 13 385.673 18.9906 0 0 -1 12 632.256 24.2126 0 0 -1 11 4.05911 12.0715 0 0 -1 10 89.4927 15.0367 0 0 1 -10 60.5064 13.0237 1 0 -1 9 4297.44 45.4880 0 0 1 -9 4237.14 39.8078 1 0 1 -8 893.402 19.7189 1 0 -1 8 883.141 21.1103 3 0 -1 8 916.694 23.0866 0 0 1 -7 24796.9 53.5237 2 0 1 -7 24841.8 80.3587 1 0 -1 7 24777.8 87.2756 3 0 1 -6 2519.41 16.3715 2 0 1 -6 2415.64 24.2343 1 0 -1 6 2434.61 26.2667 3 0 1 -5 8805.86 26.7138 2 0 -1 5 9049.78 43.8360 3 0 1 -5 8876.29 40.0022 1 0 -1 4 300.356 10.9619 3 0 1 -4 303.879 5.66819 2 0 1 -4 313.195 9.21461 1 0 1 -3 12787.5 37.1485 1 0 -1 3 12800.3 39.5339 3 0 1 -2 3790.26 17.0426 1 0 -1 2 3769.81 18.3509 3 0 1 1 19362.4 149.470 0 0 1 2 7040.33 28.7701 0 0 -1 -2 7112.23 25.3214 1 0 -1 -3 38169.4 270.314 1 0 1 3 37929.4 78.0599 0 0 1 4 1391.02 18.5777 0 0 -1 -4 1443.00 16.2031 1 0 1 5 725.620 16.2853 0 0 -1 -5 722.268 13.8837 1 0 -1 -6 6111.78 37.9317 1 0 1 6 6096.17 44.1884 0 0 -1 -7 4470.40 35.7776 1 0 1 7 4423.34 41.0294 0 0 1 8 2610.14 35.1167 0 0 -1 -8 2664.22 29.9692 1 0 1 9 437.394 19.6366 0 0 1 10 59.3015 13.4676 0 0 1 11 168.666 14.2473 0 0 1 12-32.4428 12.0008 0 0 1 13 119.878 14.4576 0 0 1 14 499.785 20.6435 0 0 -2 15 183.609 15.6827 0 0 -2 14 119.480 14.8742 0 0 -2 12 763.380 24.7368 0 0 -2 11 600.409 22.5711 0 0 2 -10 319.562 16.1460 1 0 -2 10 334.275 22.5324 0 0 -2 10 365.130 18.1028 3 0 2 -9 2009.36 28.6666 1 0 -2 9 1965.30 30.6473 3 0 2 -8 783.303 17.6229 1 0 -2 8 736.711 19.5075 3 0 2 -7 2275.60 15.6125 2 0 2 -7 2033.26 25.0184 1 0 -2 7 2078.79 26.8771 3 0 2 -6 2903.44 16.9465 2 0 -2 6 2959.94 28.9757 3 0 2 -6 2926.67 26.9471 1 0 -2 5 9230.23 44.0379 3 0 2 -5 9213.35 42.2599 1 0 2 -4 38655.6 305.993 1 0 -2 4 38514.1 80.8577 3 0 2 -3 2350.65 18.1295 1 0 -2 3 2371.86 19.0066 3 0 2 -2 41385.8 254.163 1 0 -2 2 41134.9 259.982 3 0 -2 1 1383.83 12.4476 3 0 2 -1 1388.53 12.8127 0 0 -2 0 10139.4 29.6792 3 0 2 0 10118.7 32.0320 0 0 2 1 5137.00 25.1087 0 0 2 2 454.170 10.7630 0 0 2 3 1985.98 21.0302 0 0 -2 -3 2036.12 18.0934 1 0 -2 -4 2761.00 23.1090 1 0 2 4 2712.15 26.8434 0 0 -2 -5 9952.44 46.3317 1 0 2 5 10093.7 53.9871 0 0 2 6 7580.62 51.3203 0 0 -2 -6 7655.31 44.1083 1 0 -2 -7 90.1472 10.4325 1 0 2 7 92.4153 11.9531 0 0 -2 -8 333.179 13.9022 1 0 2 8 328.857 16.2119 0 0 2 9 17.0439 12.4233 0 0 2 10 2355.91 37.8040 0 0 2 11-9.14820 14.0181 0 0 2 12 544.925 23.1254 0 0 -3 15-15.0671 16.8881 0 0 -3 14 767.940 26.7047 0 0 -3 13 386.481 21.2219 0 0 -3 12 39.8265 17.5386 0 0 3 -11 732.838 22.5946 1 0 -3 11 751.453 23.7206 3 0 3 -10 240.934 14.5857 1 0 -3 10 211.932 16.3148 3 0 3 -9 3599.36 37.7024 1 0 -3 9 3443.70 38.6910 3 0 -3 8 82.1883 11.8871 3 0 3 -8 64.3370 10.8547 1 0 -3 7 23.2691 10.3559 3 0 3 -7 0.37117 8.62631 1 0 3 -6 829.763 15.8868 1 0 -3 6 862.100 16.9945 3 0 -3 5 474.551 12.3999 3 0 3 -5 461.492 11.8453 1 0 3 -4 5157.69 31.0075 1 0 -3 4 5338.64 31.8552 3 0 3 -3 1058.10 14.2679 1 0 -3 3 1036.44 14.3759 3 0 3 -2 33414.6 74.1934 0 0 -3 2 33540.2 67.2465 3 0 -3 1 6859.94 30.4461 3 0 3 -1 6948.50 32.2915 0 0 3 0 5386.70 29.3537 0 0 -3 0 5290.05 26.5776 3 0 3 1 8272.66 36.9920 0 0 3 1 8146.80 25.9285 4 0 3 2 9055.77 42.2833 0 0 3 3 18997.3 66.2520 0 0 3 4 733.930 16.9535 0 0 -3 -5 5053.34 35.6751 1 0 3 5 5138.36 41.6051 0 0 3 6 6.81345 11.6470 0 0 -3 -6-1.32262 8.06773 1 0 3 7 0.71927 10.7529 0 0 -3 -7 42.1352 9.21438 1 0 3 8 2628.33 37.4094 0 0 3 9 393.017 20.1554 0 0 3 10 1932.37 37.1361 0 0 3 11 204.902 16.4561 0 0 3 12 1932.62 39.5018 0 0 3 13 839.574 27.8110 0 0 -4 14 93.9198 15.0606 0 0 -4 13 606.901 24.4266 3 0 -4 12 73.8208 17.5481 3 0 4 -12 89.6827 15.6874 1 0 -4 11 1499.73 30.7719 3 0 4 -11 1551.45 30.3801 1 0 -4 10 957.448 24.9220 3 0 4 -10 912.889 23.1244 1 0 4 -9 3195.84 36.4629 1 0 -4 9 3194.17 37.6240 3 0 4 -8 457.985 15.5375 1 0 -4 8 490.873 16.8307 3 0 4 -7 3924.10 35.1461 1 0 -4 7 3923.41 35.9066 3 0 4 -6 10361.9 52.3321 1 0 -4 6 10254.6 53.3344 3 0 -4 5 507.455 13.3598 3 0 4 -5 496.224 12.9804 1 0 -4 4 313.532 11.3475 3 0 4 -4 310.220 10.4282 1 0 -4 3 925.484 15.2903 3 0 -4 2 11370.0 45.6586 3 0 4 -2 11418.4 49.0677 0 0 -4 1 4790.09 29.7508 3 0 4 -1 4709.75 31.5281 0 0 -4 0 188.789 9.07041 3 0 4 0 162.002 10.0466 0 0 4 1 11704.9 50.8653 0 0 4 1 11471.5 35.4288 4 0 4 2 1300.69 19.6960 0 0 4 2 1233.16 12.4873 4 0 4 3 214.742 11.5321 0 0 4 4 9347.58 54.9408 0 0 4 5 6251.72 48.5292 0 0 4 6 505.715 17.5331 0 0 4 7 171.533 14.6737 0 0 4 8 2564.34 38.2707 0 0 4 9 529.461 22.5496 0 0 4 10 315.546 18.6552 0 0 4 11 125.160 13.3194 0 0 4 12 235.773 16.0874 0 0 -5 14 460.389 26.6126 3 0 -5 13 225.751 18.3504 3 0 -5 12 465.259 22.3845 3 0 5 -12 483.636 21.0343 1 0 5 -11 1239.77 28.5536 1 0 -5 11 1134.25 28.4439 3 0 -5 10 342.995 17.3703 3 0 5 -10 367.561 17.3308 1 0 -5 9 338.795 15.6812 3 0 5 -9 279.815 15.4263 1 0 -5 8 7023.80 51.7745 3 0 5 -8 7034.13 51.7384 1 0 -5 7 2305.76 29.0675 3 0 5 -7 2384.49 28.6731 1 0 5 -6 3768.59 34.1322 1 0 -5 6 3617.88 33.5751 3 0 -5 5 277.041 12.2773 3 0 5 -5 260.789 11.0818 1 0 5 -4 13974.5 59.4664 1 0 -5 4 14278.3 59.0033 3 0 5 -3 15.8845 9.38464 0 0 -5 3 2.16000 8.22744 3 0 5 -2 1185.90 19.7559 0 0 -5 2 1204.67 18.1580 3 0 -5 1 7.42754 8.41528 3 0 5 -1 5.28212 8.20607 0 0 5 0 88.5157 9.68618 0 0 -5 0 60.8582 7.39589 3 0 5 1 2552.83 27.7351 0 0 -5 -1 2598.90 25.6796 3 0 5 1 2492.06 19.2932 4 0 5 2 1159.94 13.2735 4 0 5 2 1224.93 20.5544 0 0 5 3 7546.31 50.1488 0 0 5 4 1586.59 26.4537 0 0 5 5 284.258 14.4607 0 0 5 6 360.134 16.2398 0 0 5 7 215.758 15.4630 0 0 5 8 2853.63 41.6268 0 0 5 9 122.705 15.1872 0 0 5 10 1440.41 33.3295 0 0 5 12-36.9088 14.1541 0 0 -6 15 1144.48 34.8386 3 0 -6 14 186.477 18.8920 3 0 -6 13 102.798 19.7546 3 0 6 -13 120.138 16.0358 1 0 -6 12 208.997 17.1894 3 0 6 -12 369.229 20.8833 1 0 6 -11 4602.29 50.9006 1 0 -6 11 4547.84 50.8091 3 0 -6 10 282.070 16.8588 3 0 6 -10 209.927 15.4484 1 0 -6 9 557.064 19.8159 3 0 6 -9 593.476 19.1171 1 0 -6 8 142.652 12.4993 3 0 6 -8 143.270 11.5738 1 0 6 -7 281.855 13.6005 1 0 -6 7 288.174 14.2163 3 0 6 -6 105.673 11.1950 1 0 -6 6 122.252 11.0672 3 0 6 -5 3256.99 32.2069 1 0 -6 5 3137.94 31.9725 3 0 -6 4 3038.74 30.6153 3 0 -6 3 148.060 11.1681 3 0 6 -3 149.725 12.3413 0 0 6 -2 16769.0 73.7649 0 0 -6 2 16886.8 67.6367 3 0 6 -1 6779.94 46.4481 0 0 -6 1 6786.54 43.0143 3 0 -6 0 213.571 10.6232 3 0 6 0 206.336 12.5905 0 0 6 1 2081.10 27.2117 0 0 -6 -1 2031.32 25.0966 3 0 6 1 2054.39 19.3436 4 0 6 2 136.730 11.8857 0 0 -6 -2 136.968 10.5890 3 0 6 3 6086.40 48.5326 0 0 6 4 156.534 11.6241 0 0 6 5 58.2377 11.9293 0 0 6 6 1486.02 29.1993 0 0 6 7 73.6992 12.7183 0 0 6 8 271.168 17.4664 0 0 6 9 8.63397 12.6359 0 0 6 10 925.087 28.1325 0 0 6 11 680.568 28.7647 0 0 -7 14 200.413 19.0429 3 0 -7 13 267.387 21.1935 3 0 7 -13 325.595 21.4003 1 0 7 -12 644.142 23.9681 1 0 -7 12 590.581 23.8123 3 0 -7 11 21.1794 13.3233 3 0 -7 10 1281.01 28.2817 3 0 7 -10 1287.95 29.1538 1 0 7 -9 3123.89 39.8137 1 0 -7 9 3128.39 39.7208 3 0 7 -8 984.415 22.4696 1 0 -7 8 945.639 22.8182 3 0 7 -7-2.27970 9.23859 1 0 -7 7 47.6023 10.7648 3 0 -7 6 735.581 19.0973 3 0 7 -6 827.302 20.0629 1 0 7 -5 508.463 16.0485 1 0 -7 5 566.425 16.6242 3 0 -7 4 1797.81 25.9683 3 0 7 -3 111.492 12.3000 0 0 -7 3 147.566 11.7736 3 0 7 -2 3680.37 38.3989 0 0 -7 2 3418.42 33.8018 3 0 7 -1 1012.41 21.2364 0 0 -7 1 959.443 19.6891 3 0 -7 0 41.3904 9.72040 3 0 7 0 4.65036 10.4623 0 0 7 1 1769.69 27.6694 0 0 -7 -1 1756.19 25.4535 3 0 -7 -2 2669.16 32.1305 3 0 7 2 2665.37 34.6728 0 0 7 3 1333.08 26.2945 0 0 7 4 137.252 12.7281 0 0 7 5 424.477 18.9661 0 0 7 6 2470.81 38.9390 0 0 7 7 78.6089 12.1693 0 0 7 9 5.61638 13.8591 0 0 7 10 172.076 16.2353 0 0 8 -14 229.699 19.5626 1 0 -8 14 76.4043 18.5248 3 0 8 -13 1156.11 31.4930 1 0 -8 13 1023.98 31.5968 3 0 -8 12 53.2411 17.8784 3 0 -8 11-24.1719 11.5745 3 0 8 -10 177.339 14.8033 1 0 -8 10 181.910 17.5244 3 0 -8 9 837.037 22.9325 3 0 8 -9 860.659 22.4959 1 0 -8 8 486.235 19.2184 3 0 8 -8 480.109 18.8550 1 0 8 -7 73.1565 11.9031 1 0 -8 7 68.2636 13.3699 3 0 8 -6 5250.22 48.0642 1 0 -8 6 5239.36 47.1876 3 0 8 -5 3031.11 36.9777 1 0 -8 5 2988.43 35.9313 3 0 -8 4 29.7186 10.5991 3 0 8 -4 22.8996 11.9052 0 0 8 -3 1212.85 26.0358 0 0 -8 3 1173.78 23.0835 3 0 -8 2 145.959 12.1599 3 0 8 -2 164.540 13.7238 0 0 8 -1 4790.27 46.2709 0 0 -8 1 4835.24 43.0414 3 0 8 0 404.436 16.6382 0 0 -8 0 293.297 14.9107 3 0 8 1-37.6759 9.65426 0 0 -8 -1-15.4908 9.15982 3 0 8 2 1307.07 26.6989 0 0 -8 -2 1256.25 24.1996 3 0 8 3 137.688 13.1500 0 0 -8 -3 123.689 12.3524 3 0 8 4 1061.56 26.5148 0 0 -8 -4 1033.13 24.0527 3 0 8 5 163.778 14.5134 0 0 8 6 616.667 21.6266 0 0 8 8 849.464 25.9586 0 0 8 9 163.469 13.3220 0 0 9 -14 162.452 18.4503 1 0 -9 13 548.899 25.0362 3 0 9 -13 735.260 28.3705 1 0 9 -12-23.3928 15.7563 1 0 -9 12 90.0994 14.3025 3 0 -9 11-2.53535 14.9399 3 0 9 -11 41.1397 14.1804 1 0 9 -10 380.162 17.9486 1 0 -9 10 475.818 21.2938 3 0 9 -9 664.188 21.6769 1 0 -9 9 486.902 20.4706 3 0 9 -8 1869.51 33.3831 1 0 -9 8 1748.95 31.0741 3 0 -9 7 348.090 17.0742 3 0 9 -7 226.135 15.9722 1 0 -9 6 85.3387 13.6651 3 0 9 -6 17.4736 11.4218 1 0 -9 5 19.4579 11.2102 3 0 9 -5 13.1914 11.9321 1 0 -9 4 147.767 13.8018 3 0 9 -4 229.586 15.9547 0 0 9 -3 3348.82 42.7632 0 0 -9 3 3305.33 39.0290 3 0 -9 2-17.8166 11.7878 3 0 9 -2 37.9865 11.9940 0 0 -9 1-17.4575 11.5311 3 0 9 -1 25.8658 10.1755 0 0 9 0 430.985 17.7886 0 0 -9 0 433.597 17.6860 3 0 -9 -1 7520.95 58.7239 3 0 9 1 7495.46 63.5236 0 0 -9 -2 336.372 16.4732 3 0 9 2 332.061 17.5479 0 0 -9 -3-6.84067 9.48751 3 0 9 4 2.09726 9.78638 0 0 -9 -5 30.5179 14.1403 3 0 9 5 147.841 12.1067 0 0 9 6 22.1518 10.8938 0 0 9 7 32.0993 11.9309 0 0 9 8 211.323 18.1769 0 0 10 -12 136.274 16.2849 1 0 10 -11-30.7933 13.2695 1 0 10 -10 388.252 19.1122 1 0 -10 8 1993.87 35.3723 3 0 10 -8 2136.09 37.3831 1 0 -10 7 1638.33 31.6100 3 0 10 -7 1823.55 33.9015 1 0 -10 6 1336.57 28.7702 3 0 10 -6 1418.66 29.4899 1 0 -10 5 78.1982 12.6365 3 0 10 -5 157.295 14.0438 1 0 10 -4 73.2582 12.6564 0 0 -10 4 27.2965 15.4776 3 0 -10 3 206.272 15.0820 3 0 10 -3 248.197 16.9793 0 0 10 -2 238.875 16.5899 0 0 -10 2 343.515 17.9649 3 0 -10 1 250.784 17.0662 3 0 10 -1 111.377 11.9400 0 0 -10 0 568.190 20.7158 3 0 10 0 606.545 20.2519 0 0 10 1 78.2288 13.1920 0 0 -10 -1-18.5870 9.52719 3 0 10 2 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50.2863 16.8777 5 5 -3 -2 191.500 16.1098 2 -5 3 2 241.356 21.1647 5 5 -3 -1 63.6103 16.1833 2 -5 3 1 35.4105 18.2650 5 5 -3 0 135.556 15.2098 2 -5 3 0-2.24878 14.5819 5 -5 3 -1 178.515 21.0399 5 -5 3 -2 726.033 28.3597 5 -5 3 -3 52.1315 16.8814 5 -5 3 -4 64.9364 17.8532 5 -5 3 -5 5.05913 16.3391 5 -5 3 -5 121.617 20.6808 1 -5 3 -6 94.6003 21.7962 1 -5 3 -7 114.801 21.7009 1 5 -2 -7 126.428 19.5041 2 -5 2 7 180.039 21.0009 5 -5 2 6-17.9492 15.6443 5 5 -2 -5 618.485 24.7146 2 -5 2 5 569.024 25.5251 5 5 -2 -4 103.730 15.3230 2 -5 2 4 74.4310 18.9149 5 5 -2 -2 196.469 17.5064 2 -5 2 2 46.3526 19.0455 5 -5 2 1 212.416 22.5147 5 5 -2 -1 72.3748 14.2216 2 5 -2 0 100.303 14.9258 2 -5 2 0 85.2324 15.7149 5 -5 2 -1 380.099 23.7908 5 -5 2 -4 106.471 20.1825 5 -5 2 -4 52.7481 19.8377 1 -5 2 -5 372.378 22.6637 5 -5 2 -5 192.530 21.9621 1 -5 2 -6 47.8562 20.2699 1 -5 2 -7 132.052 23.6090 1 5 -1 -7 95.5290 18.2771 2 -5 1 7 25.5705 19.3077 5 5 -1 -6 377.824 24.3773 2 -5 1 6 177.205 18.6606 5 5 -1 -5 19.6714 15.8594 2 -5 1 5 50.4711 17.7611 5 5 -1 -4 154.098 16.3060 2 -5 1 4 153.273 19.8210 5 -5 1 3 92.0723 19.0678 5 5 -1 -3 81.5906 14.3865 2 -5 1 2 462.703 21.8852 5 -5 1 1 96.7736 17.6998 5 -5 1 0 153.054 15.1300 5 -5 1 -1 124.673 16.2838 5 -5 1 -2 521.850 23.6497 5 -5 1 -3 206.422 16.7596 5 -5 1 -3-21.7609 16.7242 1 -5 1 -4 544.567 24.0721 5 -5 1 -4 421.797 26.8351 1 -5 1 -5 254.139 17.5880 5 -5 1 -5 17.6037 21.2457 1 5 0 -7 208.987 21.9681 2 -5 0 7 308.943 25.1409 5 -5 0 6 95.0069 18.6155 5 -5 0 5 222.976 16.0733 5 -5 0 4 174.268 15.9220 5 -5 0 3 46.9466 11.2025 5 -5 0 1 202.803 16.8555 5 -5 0 0 170.024 16.3198 5 -5 0 -1 58.8943 13.1288 5 -5 0 -2 5.79346 13.3685 5 -5 0 -2-34.3255 16.8609 1 -5 0 -3 205.668 23.7945 1 -5 0 -3 84.7048 14.8044 5 -5 0 -4 18.9546 19.4521 1 -5 0 -5 545.425 21.5833 5 -5 0 -5 808.974 32.7289 1 -5 0 -6 27.0424 21.3892 1 5 1 -7 284.879 20.7849 2 -5 -1 7 536.608 21.7959 5 -5 -1 6 116.565 14.9594 5 -5 -1 5-25.5489 14.1335 5 -5 -1 4 254.488 16.4433 5 -5 -1 3 152.365 16.9179 5 -5 -1 2 204.974 17.0043 5 -5 -1 1 37.4328 14.9082 5 -5 -1 0 126.213 14.2112 5 -5 -1 -1 114.603 17.3519 5 -5 -1 -2 346.369 20.3843 5 -5 -1 -3 298.890 23.2267 1 -5 -1 -3 184.965 17.6854 5 -5 -1 -4-33.9389 13.5588 5 -5 -1 -5 65.1017 24.8280 1 -5 -2 6 306.616 16.0561 5 -5 -2 4 187.342 15.2536 5 -5 -2 2 285.528 18.6458 5 -5 -2 1 263.342 19.7090 5 -5 -2 0 95.0240 13.5156 5 -5 -2 -1 127.784 16.4180 5 -5 -2 -2 82.8818 13.6718 5 -5 -2 -3 337.396 21.7267 5 -5 -2 -4 76.7424 15.4423 5 -5 -3 6-6.96428 13.2805 5 -5 -3 5 13.9288 14.8489 5 -5 -3 4 72.3614 14.9628 5 -5 -3 2 105.628 15.5337 5 -5 -3 1 79.1154 14.3519 5 -5 -3 0 73.1867 18.5249 5 -5 -3 -1 98.0092 16.6957 5 -5 -3 -2 146.612 17.8654 5 -5 -3 -3 193.714 15.9245 5 -5 -3 -4 128.913 18.3385 5 -5 -4 5 76.7630 18.2001 5 -5 -4 4-11.7335 15.7991 5 -5 -4 2 91.6930 16.4423 5 -5 -4 1 193.091 17.4480 5 -5 -4 0 368.649 22.3812 5 -5 -4 -1 235.668 18.5623 5 ; _shelx_hkl_checksum 38183 _shelx_res_file ; TITL SAT19 P-1 shelx.res created by SHELXL-2018/3 at 10:20:36 on 22-Sep-2026 CELL 0.71073 4.5764 10.8730 12.0930 102.870 92.650 99.040 ZERR 2.00 0.0009 0.0020 0.0020 0.010 0.010 0.010 LATT 1 SFAC C H N O CL S UNIT 18 16 4 2 4 2 MERG 2 SHEL 13 0.835 DFIX 0.86 0.02 N1 H1N N2 H2N HTAB N1 O1 HTAB N2 S1_$1 EQIV $1 -x, -y+2, -z HTAB C9 S1_$1 EQIV $2 -x, -y+1, -z HTAB C9 Cl1_$2 HTAB N1 O1 HTAB N2 S1_$1 HTAB C9 Cl1_$2 HTAB C9 S1_$1 HTAB N1 O1 HTAB N2 S1_$1 FMAP 2 PLAN 30 SIZE 0.100 0.140 0.480 ACTA BOND $H CONF LIST 4 L.S. 14 WGHT 0.018900 1.373900 FVAR 3.03782 0.91828 C1 1 -0.114639 0.704152 0.240677 11.00000 0.05390 0.03886 = 0.03639 0.00977 0.00201 -0.01081 C2 1 0.042378 0.605588 0.241151 11.00000 0.05225 0.04188 = 0.03327 0.00496 0.00510 -0.00934 AFIX 43 H2 2 0.074750 0.551893 0.173074 11.00000 -1.20000 AFIX 0 C3 1 0.151092 0.587653 0.344245 11.00000 0.04651 0.04770 = 0.03984 0.01330 -0.00241 -0.00896 C4 1 0.107258 0.667198 0.445591 11.00000 0.06502 0.05037 = 0.03895 0.01752 -0.00602 -0.01238 AFIX 43 H4 2 0.183289 0.655586 0.514480 11.00000 -1.20000 AFIX 0 C5 1 -0.051207 0.764194 0.442959 11.00000 0.08205 0.04537 = 0.02889 0.00821 0.00959 -0.01066 C6 1 -0.165603 0.783766 0.341384 11.00000 0.06872 0.04211 = 0.04324 0.01247 0.00741 0.00097 AFIX 43 H6 2 -0.274366 0.849115 0.341043 11.00000 -1.20000 AFIX 0 C7 1 -0.145928 0.818814 0.090235 11.00000 0.04529 0.04050 = 0.02744 0.00664 0.00442 0.00685 C8 1 -0.534110 0.734633 -0.072524 11.00000 0.05371 0.04879 = 0.03507 0.00619 0.00106 -0.00223 C9 1 -0.659577 0.774457 -0.173464 11.00000 0.05695 0.06207 = 0.04641 0.01275 -0.00919 0.00080 AFIX 127 H9A 2 -0.504337 0.791366 -0.221559 21.00000 -1.50000 H9B 2 -0.743052 0.850490 -0.147804 21.00000 -1.50000 H9C 2 -0.811532 0.706967 -0.215545 21.00000 -1.50000 H9D 2 -0.868277 0.774516 -0.168380 -21.00000 -1.50000 H9E 2 -0.629562 0.715392 -0.242135 -21.00000 -1.50000 H9F 2 -0.561082 0.858915 -0.174394 -21.00000 -1.50000 AFIX 0 N1 3 -0.235286 0.719527 0.133625 11.00000 0.06225 0.04534 = 0.03400 0.01651 -0.00470 -0.00965 N2 3 -0.292966 0.820747 -0.012933 11.00000 0.04748 0.04110 = 0.03810 0.01378 0.00218 0.00032 O1 4 -0.636065 0.637267 -0.044155 11.00000 0.08863 0.06509 = 0.05339 0.02217 -0.01711 -0.02882 CL1 5 0.343400 0.462338 0.345011 11.00000 0.06515 0.07300 = 0.07027 0.02498 -0.00363 0.01228 CL2 5 -0.113262 0.863607 0.571615 11.00000 0.15343 0.06274 = 0.03796 0.00375 0.02119 0.00548 S1 6 0.133067 0.938613 0.149235 11.00000 0.05339 0.04521 = 0.04161 0.01731 -0.00595 -0.00696 H1N 2 -0.375741 0.662243 0.094643 11.00000 -1.20000 H2N 2 -0.230919 0.890351 -0.033336 11.00000 -1.20000 HKLF 4 REM SAT19 P-1 REM wR2 = 0.1391, GooF = S = 1.327, Restrained GooF = 1.327 for all data REM R1 = 0.0648 for 1747 Fo > 4sig(Fo) and 0.0779 for all 2007 data REM 144 parameters refined using 2 restraints END WGHT 0.0189 1.3740 REM Highest difference peak 0.461, deepest hole -0.398, 1-sigma level 0.070 Q1 1 -0.2823 0.9060 0.5415 11.00000 0.05 0.46 Q2 1 0.3117 0.5329 0.3936 11.00000 0.05 0.34 Q3 1 0.0919 0.6757 0.2458 11.00000 0.05 0.28 Q4 1 -0.0599 0.9640 0.1605 11.00000 0.05 0.26 Q5 1 0.1530 0.4936 0.3868 11.00000 0.05 0.26 Q6 1 0.1093 0.9942 0.2662 11.00000 0.05 0.25 Q7 1 0.3829 0.7468 0.4565 11.00000 0.05 0.24 Q8 1 0.0096 0.5600 0.1944 11.00000 0.05 0.24 Q9 1 0.1127 0.8948 0.5583 11.00000 0.05 0.23 Q10 1 -0.7587 0.5943 -0.0530 11.00000 0.05 0.23 Q11 1 -0.5054 0.6056 -0.0806 11.00000 0.05 0.22 Q12 1 0.3591 0.4000 0.2327 11.00000 0.05 0.22 Q13 1 0.1924 0.8737 0.3626 11.00000 0.05 0.21 Q14 1 0.0226 0.8192 0.4026 11.00000 0.05 0.21 Q15 1 -0.1644 0.8180 0.4966 11.00000 0.05 0.20 Q16 1 -0.7947 0.5707 -0.2409 11.00000 0.05 0.20 Q17 1 0.1183 0.9810 0.0976 11.00000 0.05 0.20 Q18 1 0.5142 0.9471 0.1622 11.00000 0.05 0.20 Q19 1 0.3103 0.8392 0.4981 11.00000 0.05 0.20 Q20 1 -0.7645 0.6597 -0.0737 11.00000 0.05 0.20 Q21 1 0.1304 0.6622 0.6416 11.00000 0.05 0.20 Q22 1 0.2619 0.8242 0.4525 11.00000 0.05 0.19 Q23 1 -0.4935 0.9046 0.0632 11.00000 0.05 0.19 Q24 1 -0.7683 0.9966 -0.1914 11.00000 0.05 0.19 Q25 1 -0.5354 0.8346 0.3178 11.00000 0.05 0.19 Q26 1 -0.4332 0.7562 0.3590 11.00000 0.05 0.19 Q27 1 0.3568 0.8933 0.6183 11.00000 0.05 0.19 Q28 1 -0.3176 0.9576 0.0876 11.00000 0.05 0.19 Q29 1 0.1485 0.5788 0.2787 11.00000 0.05 0.19 Q30 1 -0.9446 0.6320 -0.2583 11.00000 0.05 0.19 ; _shelx_res_checksum 6869 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C C1 -0.1146(11) 0.7042(4) 0.2407(4) 0.0450(11) Uani d 1 . . C C2 0.0424(11) 0.6056(4) 0.2412(4) 0.0450(11) Uani d 1 . . H H2 0.074750 0.551893 0.173074 0.054 Uiso calc 1 . . C C3 0.1511(10) 0.5877(5) 0.3442(4) 0.0463(11) Uani d 1 . . C C4 0.1073(12) 0.6672(5) 0.4456(4) 0.0531(13) Uani d 1 . . H H4 0.183289 0.655586 0.514480 0.064 Uiso calc 1 . . C C5 -0.0512(13) 0.7642(5) 0.4430(4) 0.0544(14) Uani d 1 . . C C6 -0.1656(12) 0.7838(5) 0.3414(4) 0.0518(13) Uani d 1 . . H H6 -0.274366 0.849115 0.341043 0.062 Uiso calc 1 . . C C7 -0.1459(10) 0.8188(4) 0.0902(3) 0.0380(10) Uani d 1 . . C C8 -0.5341(11) 0.7346(5) -0.0725(4) 0.0477(12) Uani d 1 . . C C9 -0.6596(12) 0.7745(5) -0.1735(4) 0.0566(13) Uani d 1 . . H H9A -0.504337 0.791366 -0.221559 0.085 Uiso calc 0.92(6) . . H H9B -0.743052 0.850490 -0.147804 0.085 Uiso calc 0.92(6) . . H H9C -0.811532 0.706967 -0.215545 0.085 Uiso calc 0.92(6) . . H H9D -0.868277 0.774516 -0.168380 0.085 Uiso calc 0.08(6) . . H H9E -0.629562 0.715392 -0.242135 0.085 Uiso calc 0.08(6) . . H H9F -0.561082 0.858915 -0.174394 0.085 Uiso calc 0.08(6) . . N N1 -0.2353(10) 0.7195(4) 0.1336(3) 0.0484(10) Uani d 1 . . N N2 -0.2930(9) 0.8207(4) -0.0129(3) 0.0424(9) Uani d 1 . . O O1 -0.6361(9) 0.6373(4) -0.0442(3) 0.0731(12) Uani d 1 . . Cl Cl1 0.3434(3) 0.46234(15) 0.34501(13) 0.0684(4) Uani d 1 . . Cl Cl2 -0.1133(5) 0.86361(15) 0.57162(12) 0.0870(6) Uani d 1 . . S S1 0.1331(3) 0.93861(12) 0.14923(10) 0.0476(3) Uani d 1 . . H H1N -0.376(8) 0.662(4) 0.095(4) 0.057 Uiso d 1 . . H H2N -0.231(11) 0.890(3) -0.033(4) 0.057 Uiso d 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.054(3) 0.039(3) 0.036(2) -0.011(2) 0.002(2) 0.010(2) C2 0.052(3) 0.042(3) 0.033(2) -0.009(2) 0.005(2) 0.005(2) C3 0.047(3) 0.048(3) 0.040(3) -0.009(2) -0.002(2) 0.013(2) C4 0.065(3) 0.050(3) 0.039(3) -0.012(3) -0.006(2) 0.018(2) C5 0.082(4) 0.045(3) 0.029(2) -0.011(3) 0.010(2) 0.008(2) C6 0.069(3) 0.042(3) 0.043(3) 0.001(2) 0.007(2) 0.012(2) C7 0.045(3) 0.041(2) 0.027(2) 0.007(2) 0.0044(18) 0.0066(18) C8 0.054(3) 0.049(3) 0.035(2) -0.002(2) 0.001(2) 0.006(2) C9 0.057(3) 0.062(3) 0.046(3) 0.001(3) -0.009(2) 0.013(3) N1 0.062(3) 0.045(2) 0.034(2) -0.0096(19) -0.0047(18) 0.0165(18) N2 0.047(2) 0.041(2) 0.038(2) 0.0003(18) 0.0022(17) 0.0138(17) O1 0.089(3) 0.065(3) 0.053(2) -0.029(2) -0.017(2) 0.0222(19) Cl1 0.0651(9) 0.0730(10) 0.0703(9) 0.0123(7) -0.0036(7) 0.0250(8) Cl2 0.1534(17) 0.0627(9) 0.0380(7) 0.0055(10) 0.0212(9) 0.0037(6) S1 0.0534(7) 0.0452(7) 0.0416(7) -0.0070(5) -0.0059(5) 0.0173(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' Cl Cl 0.1484 0.1585 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C6 C1 C2 . . 120.8(5) ? C6 C1 N1 . . 120.3(5) ? C2 C1 N1 . . 118.9(4) ? C1 C2 C3 . . 119.2(4) ? C1 C2 H2 . . 120.4 ? C3 C2 H2 . . 120.4 ? C4 C3 C2 . . 121.0(5) ? C4 C3 Cl1 . . 119.8(4) ? C2 C3 Cl1 . . 119.3(4) ? C5 C4 C3 . . 118.7(5) ? C5 C4 H4 . . 120.7 ? C3 C4 H4 . . 120.7 ? C4 C5 C6 . . 121.7(5) ? C4 C5 Cl2 . . 118.8(4) ? C6 C5 Cl2 . . 119.4(4) ? C1 C6 C5 . . 118.6(5) ? C1 C6 H6 . . 120.7 ? C5 C6 H6 . . 120.7 ? N1 C7 N2 . . 116.6(4) ? N1 C7 S1 . . 124.4(3) ? N2 C7 S1 . . 119.0(3) ? O1 C8 N2 . . 122.8(4) ? O1 C8 C9 . . 123.6(4) ? N2 C8 C9 . . 113.6(4) ? C8 C9 H9A . . 109.5 ? C8 C9 H9B . . 109.5 ? H9A C9 H9B . . 109.5 ? C8 C9 H9C . . 109.5 ? H9A C9 H9C . . 109.5 ? H9B C9 H9C . . 109.5 ? C8 C9 H9D . . 109.5 ? H9A C9 H9D . . 141.1 ? H9B C9 H9D . . 56.3 ? H9C C9 H9D . . 56.3 ? C8 C9 H9E . . 109.5 ? H9A C9 H9E . . 56.3 ? H9B C9 H9E . . 141.1 ? H9C C9 H9E . . 56.3 ? H9D C9 H9E . . 109.5 ? C8 C9 H9F . . 109.5 ? H9A C9 H9F . . 56.3 ? H9B C9 H9F . . 56.3 ? H9C C9 H9F . . 141.1 ? H9D C9 H9F . . 109.5 ? H9E C9 H9F . . 109.5 ? C7 N1 C1 . . 123.9(4) ? C7 N1 H1N . . 116(4) ? C1 N1 H1N . . 120(4) ? C8 N2 C7 . . 127.8(4) ? C8 N2 H2N . . 121(4) ? C7 N2 H2N . . 111(4) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 C6 . 1.381(7) ? C1 C2 . 1.382(7) ? C1 N1 . 1.438(6) ? C2 C3 . 1.386(6) ? C2 H2 . 0.9300 ? C3 C4 . 1.377(7) ? C3 Cl1 . 1.736(5) ? C4 C5 . 1.376(7) ? C4 H4 . 0.9300 ? C5 C6 . 1.386(7) ? C5 Cl2 . 1.749(5) ? C6 H6 . 0.9300 ? C7 N1 . 1.320(6) ? C7 N2 . 1.396(5) ? C7 S1 . 1.678(4) ? C8 O1 . 1.216(6) ? C8 N2 . 1.384(6) ? C8 C9 . 1.502(7) ? C9 H9A . 0.9600 ? C9 H9B . 0.9600 ? C9 H9C . 0.9600 ? C9 H9D . 0.9600 ? C9 H9E . 0.9600 ? C9 H9F . 0.9600 ? N1 H1N . 0.859(19) ? N2 H2N . 0.858(19) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1N O1 . 0.859(19) 1.95(4) 2.655(5) 138(5) yes N2 H2N S1 2_575 0.858(19) 2.57(2) 3.395(4) 163(5) yes C9 H9F S1 2_575 0.96 2.66 3.576(5) 160.2 yes C9 H9E Cl1 2_565 0.96 2.62 3.478(6) 148.7 yes 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C6 C1 C2 C3 . . . . -0.5(7) ? N1 C1 C2 C3 . . . . -177.9(4) ? C1 C2 C3 C4 . . . . -0.6(7) ? C1 C2 C3 Cl1 . . . . 179.0(3) ? C2 C3 C4 C5 . . . . 1.0(7) ? Cl1 C3 C4 C5 . . . . -178.6(4) ? C3 C4 C5 C6 . . . . -0.3(8) ? C3 C4 C5 Cl2 . . . . 178.8(4) ? C2 C1 C6 C5 . . . . 1.2(7) ? N1 C1 C6 C5 . . . . 178.6(4) ? C4 C5 C6 C1 . . . . -0.8(8) ? Cl2 C5 C6 C1 . . . . -179.9(4) ? N2 C7 N1 C1 . . . . -178.1(4) ? S1 C7 N1 C1 . . . . 3.3(7) ? C6 C1 N1 C7 . . . . 68.6(7) ? C2 C1 N1 C7 . . . . -113.9(5) ? O1 C8 N2 C7 . . . . -5.9(8) ? C9 C8 N2 C7 . . . . 173.0(4) ? N1 C7 N2 C8 . . . . 4.2(7) ? S1 C7 N2 C8 . . . . -177.1(4) ?