#------------------------------------------------------------------------------
#$Date: 2018-01-13 08:30:40 +0200 (Sat, 13 Jan 2018) $
#$Revision: 205177 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/86/1548669.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_1548669
loop_
_publ_author_name
'El-Hiti, Gamal A.'
'Mohamed, Hanan A.'
'Abdel-Wahab, Bakr F.'
'Alotaibi, Mohammad Hayal'
'Hegazy, Amany S.'
'Kariuki, Benson M.'
_publ_section_title
;
Ethyl
(Z)-2-[2-(4-methylphenyl)hydrazin-1-ylidene]-3-oxo-3-(thiazol-2-ylamino)propanoate
;
_journal_coeditor_code HB4198
_journal_issue 1
_journal_name_full IUCrData
_journal_page_first x171852
_journal_paper_doi 10.1107/S2414314617018521
_journal_volume 3
_journal_year 2018
_chemical_formula_iupac 'C15 H16 N4 O3 S'
_chemical_formula_moiety 'C15 H16 N4 O3 S'
_chemical_formula_sum 'C15 H16 N4 O3 S'
_chemical_formula_weight 332.38
_chemical_name_systematic
'Ethyl (Z)-2-[2-(4-methylphenyl)hydrazin-1-ylidene]-3-oxo-3-(thiazol-2-ylamino)propanoate'
_space_group_crystal_system orthorhombic
_space_group_IT_number 19
_space_group_name_Hall 'P 2ac 2ab'
_space_group_name_H-M_alt 'P 21 21 21'
_symmetry_space_group_name_Hall 'P 2ac 2ab'
_symmetry_space_group_name_H-M 'P 21 21 21'
_atom_sites_solution_hydrogens geom
_audit_creation_method SHELXL-2013
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 5.6487(3)
_cell_length_b 16.7479(11)
_cell_length_c 16.9726(14)
_cell_measurement_reflns_used 1846
_cell_measurement_temperature 298(2)
_cell_measurement_theta_max 26.8230
_cell_measurement_theta_min 3.7780
_cell_volume 1605.67(19)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2014)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and CHEMDRAW Ultra (Cambridge Soft,
2001)
;
_computing_structure_refinement 'SHELXL2013 (Sheldrick, 20015)'
_computing_structure_solution
;
SHELXS2013 (Sheldrick, 2008)
;
_diffrn_ambient_temperature 298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_device_type 'Agilent SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0218
_diffrn_reflns_limit_h_max 5
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -23
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_limit_l_min -22
_diffrn_reflns_number 5888
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 29.747
_diffrn_reflns_theta_min 3.418
_diffrn_standards_decay_% 0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time 0
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.222
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.75580
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Agilent 2014)
;
_exptl_crystal_colour yellow
_exptl_crystal_density_diffrn 1.375
_exptl_crystal_description block
_exptl_crystal_F_000 696
_exptl_crystal_size_max 0.182
_exptl_crystal_size_mid 0.179
_exptl_crystal_size_min 0.114
_refine_diff_density_max 0.176
_refine_diff_density_min -0.188
_refine_ls_abs_structure_details
;
Flack x determined
using 863 quotients
[(I^+^)-(I^-^)]/[(I^+^)+(I^-^)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack 0.02(5)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.072
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 210
_refine_ls_number_reflns 3601
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.072
_refine_ls_R_factor_all 0.0697
_refine_ls_R_factor_gt 0.0477
_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^)+(0.0542P)^2^+0.2718P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1135
_refine_ls_wR_factor_ref 0.1297
_reflns_number_gt 2691
_reflns_number_total 3601
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file hb4198sup1.cif
_cod_data_source_block I
_cod_database_code 1548669
_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 0.961
_shelx_estimated_absorpt_t_max 0.975
_shelx_hkl_file
;
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0 0 8 32844.2 493.389 2
0 0 9 65.7949 31.6237 2
0 0 10 4538.59 206.743 2
0 0 -11 209.532 63.0938 2
0 0 11 74.8800 35.2201 2
0 0 -12 324.359 71.3469 2
0 0 12 232.581 54.7232 2
0 0 -13 225.572 69.1796 2
0 0 13 141.362 45.5187 2
0 0 -14 453.278 91.0727 2
0 0 -15 119.531 59.7154 2
0 0 -16 784.603 123.038 2
0 0 -17 21.8147 51.8714 2
0 0 -18 265.379 79.0686 2
0 0 -19-17.7170 43.9909 2
0 0 -20 185.767 77.8259 2
0 0 -21 28.8747 50.7451 2
0 1 3 3186.37 95.8978 2
0 -1 3 3085.85 95.8615 2
0 1 4 113017. 642.305 2
0 -1 4 113065. 663.635 2
0 -1 5 4409.26 143.526 2
0 1 5 4238.33 139.698 2
0 -1 6 1109.66 81.8202 2
0 1 6 1193.43 81.4379 2
0 1 7 75.8069 26.9888 2
0 -1 7 112.856 31.6385 2
0 1 8 15545.7 339.110 2
0 -1 8 14951.7 336.765 2
0 -1 9 1804.29 125.503 2
0 1 9 1914.91 127.666 2
0 -1 10 23215.4 467.262 2
0 1 10 22993.3 465.357 2
0 -1 11 3904.82 201.563 2
0 1 -11 3670.84 204.407 2
0 1 11 3624.54 194.419 2
0 -1 12 3452.08 199.277 2
0 -1 -12 3137.24 198.828 2
0 1 -12 3203.83 200.857 2
0 1 12 3543.15 201.237 2
0 1 -13 5106.91 265.390 2
0 -1 -13 4871.81 257.343 2
0 1 13 5072.69 253.927 2
0 -1 13 5086.36 252.506 2
0 1 -14 693.753 105.678 2
0 -1 -14 751.391 108.367 2
0 1 -15 158.687 62.3924 2
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0 -1 -16-104.561 54.5664 2
0 1 -16-23.4387 51.7819 2
0 -1 -17 15.5271 44.4018 2
0 1 -17-67.8812 66.6271 2
0 -1 -18 1108.17 156.094 2
0 1 -18 1026.14 150.977 2
0 -1 -19 79.8799 66.4144 2
0 1 -19-33.6519 48.9055 2
0 1 -20 454.560 105.610 2
0 -1 -20 498.745 112.755 2
0 -1 -21 99.0186 68.3517 2
0 1 -21 66.4483 60.5880 2
0 2 2 3137.91 85.0441 2
0 -2 3 53833.2 421.673 2
0 2 3 55093.9 408.364 2
0 2 4 21016.0 285.437 2
0 -2 4 22559.9 302.803 2
0 -2 5 495.938 52.0475 2
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0 2 7 1510.03 102.284 2
0 -2 7 1693.65 108.551 2
0 2 8 5363.99 202.044 2
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0 2 10 5494.77 229.271 2
0 -2 10 6032.86 239.845 2
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0 2 -11 97.4848 48.7644 2
0 2 11 181.161 47.7268 2
0 2 12 2727.86 178.128 2
0 -2 12 2590.87 173.538 2
0 2 -12 2511.83 179.095 2
0 -2 -12 2448.46 177.148 2
0 -2 13 577.685 87.4659 2
0 -2 -13 527.645 89.7923 2
0 2 -13 667.685 103.840 2
0 2 -14 18.6627 41.3060 2
0 -2 -14 2.60764 45.6066 2
0 2 -15 103.800 55.8730 2
0 -2 -15 133.738 59.4478 2
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0 2 -16 653.106 111.808 2
0 2 -17 1662.73 181.814 2
0 -2 -17 1451.79 172.046 2
0 -2 -18 79.6695 67.2304 2
0 2 -18 97.2638 63.8900 2
0 2 -19 322.303 93.5086 2
0 -2 -19 182.448 73.5044 2
0 -2 -20 110.402 64.3620 2
0 -2 -21-11.7746 52.7885 2
0 -3 1 1232.34 41.1203 1
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0 3 4 3902.11 128.758 2
0 3 5 13660.3 259.364 2
0 -3 5 13748.3 268.628 2
0 -3 6 11200.3 261.396 2
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0 3 7 9945.33 260.457 2
0 3 8 712.256 76.2071 2
0 -3 8 561.787 69.6365 2
0 3 -8 526.265 73.3196 2
0 -3 9 15284.1 368.568 2
0 3 9 14672.3 358.189 2
0 -3 10 1315.34 115.109 2
0 3 10 1339.35 114.547 2
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0 3 -11 23.4305 44.6017 2
0 -3 12 2830.20 184.469 2
0 3 -12 3632.32 225.855 2
0 -3 -12 3552.13 214.625 2
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0 -3 13 4677.52 247.170 2
0 3 -13 5049.59 269.193 2
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0 -3 -14-24.1884 47.1503 2
0 -3 -15 1840.62 177.645 2
0 3 -15 1989.30 185.477 2
0 -3 -16 360.730 90.4484 2
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0 -3 -21 590.716 131.100 2
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0 4 -3 65.4239 18.1526 1
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0 7 -3 1649.09 77.1468 1
0 -7 3 1803.29 77.1062 1
0 -7 -4 213.047 39.9660 2
0 7 -4 181.206 28.0084 1
0 7 -5 5297.06 150.873 1
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0 -8 3 1814.40 82.8613 1
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-6 -6 -8 123.643 52.4329 1
-6 -6 -8 118.062 55.0888 2
-6 -6 -7 21.3776 27.7545 1
-6 -6 -7 13.3391 30.8216 2
-6 -6 -6 57.0296 38.1643 2
-6 -6 -6 23.1875 31.8161 1
-6 -6 -5 21.2462 34.6968 1
-6 -6 -5 17.5726 31.1044 2
-6 -6 -4 40.9134 31.5638 1
-6 -6 -4 1.37677 28.5043 2
-6 -6 -3 97.8534 48.4223 1
-6 -6 -2 59.9566 39.2507 1
-6 -6 -1 190.771 58.7904 1
-6 -6 0 332.076 75.3275 1
-6 -6 1 305.504 73.1229 1
-6 -6 2 16.4722 30.2560 1
-6 -6 3 40.7381 42.0593 1
-6 -6 4-6.99419 33.0671 1
-6 -7 -13 161.733 70.5786 2
-6 -7 -12 78.9933 51.6297 2
-6 -7 -11 386.386 97.7597 2
-6 -7 -10 251.193 67.8499 1
-6 -7 -10 104.824 58.9688 2
-6 -7 -9-4.55734 26.8252 1
-6 -7 -9-0.28758 33.7770 2
-6 -7 -8 254.765 68.4695 1
-6 -7 -8 243.883 67.6299 2
-6 -7 -7 34.7253 40.8742 2
-6 -7 -7 51.5012 38.4475 1
-6 -7 -6-79.7296 45.7521 2
-6 -7 -6 58.9052 38.8089 1
-6 -7 -5 259.266 68.8048 1
-6 -7 -5 227.521 67.6247 2
-6 -7 -4 167.961 53.7462 1
-6 -7 -4 96.8684 43.5566 2
-6 -7 -3 392.668 80.6500 1
-6 -7 -2 142.666 54.9306 1
-6 -7 -1 10.7341 29.8483 1
-6 -7 0 470.473 84.9422 1
-6 -7 1 85.8908 49.4820 1
-6 -7 2 126.092 50.2450 1
-6 -7 3 322.992 76.9133 1
-6 -7 4 59.2939 40.1096 1
-6 -8 -13 139.260 63.5526 2
-6 -8 -12 62.7225 58.9423 2
-6 -8 -11 65.2886 56.1739 2
-6 -8 -10 86.6394 48.4483 2
-6 -8 -9-2.64160 29.5050 1
-6 -8 -9-102.804 54.5530 2
-6 -8 -8 149.108 60.7362 1
-6 -8 -8 177.235 64.9537 2
-6 -8 -7 29.1049 39.6650 2
-6 -8 -7 107.590 51.7001 1
-6 -8 -6 8.60896 27.7202 1
-6 -8 -6-41.6140 36.4439 2
-6 -8 -5 32.2744 36.2417 1
-6 -8 -5 20.2636 39.0137 2
-6 -8 -4 85.0893 45.0218 1
-6 -8 -4-125.241 52.7524 2
-6 -8 -3 70.6236 39.9808 1
-6 -8 -2 261.651 72.3362 1
-6 -8 -1 469.849 90.6129 1
-6 -8 0 136.138 52.2358 1
-6 -8 1 407.497 83.3913 1
-6 -8 2 284.125 71.4352 1
-6 -8 3-26.7837 32.3451 1
-6 -8 4 23.2554 28.3776 1
-6 -8 5 4.33571 25.6990 1
-6 -9 -11 149.398 70.9253 2
-6 -9 -10 4.64745 27.1621 2
-6 -9 -9 33.2219 38.3473 2
-6 -9 -8 15.5802 33.6189 2
-6 -9 -7 16.3877 37.8194 2
-6 -9 -7-20.9233 40.3518 1
-6 -9 -6 98.5765 46.1928 1
-6 -9 -6 204.325 66.7134 2
-6 -9 -5 22.4456 27.2183 1
-6 -9 -5 83.0673 47.5352 2
-6 -9 -4 168.480 60.2745 1
-6 -9 -4 15.2520 35.0631 2
-6 -9 -3 312.633 78.6293 1
-6 -9 -2 44.4765 40.3102 1
-6 -9 -1 216.212 65.3323 1
-6 -9 0-13.9924 29.4913 1
-6 -9 1 182.869 56.9437 1
-6 -9 2-22.7270 39.2670 1
-6 -9 3 289.056 77.7430 1
-6 -9 4 67.4524 44.9275 1
-6 -9 5 14.0528 37.8686 1
-6 -10 -10 6.94394 25.6444 2
-6 -10 -9-13.6345 37.5076 2
-6 -10 -8-12.8505 30.6358 2
-6 -10 -7 145.528 66.9618 2
-6 -10 -6 23.8372 34.7152 1
-6 -10 -6-6.67984 32.8035 2
-6 -10 -5 32.4985 43.7279 1
-6 -10 -5 48.9945 39.7667 2
-6 -10 -4 67.9240 33.6410 1
-6 -10 -4-75.0726 47.9430 2
-6 -10 -3 74.9673 42.5627 1
-6 -10 -2 356.421 83.5542 1
-6 -10 -1 158.389 63.1865 1
-6 -10 0 10.3406 28.9351 1
-6 -10 1 284.034 75.9872 1
-6 -10 2 167.540 66.1282 1
-6 -10 3 53.3105 42.1252 1
-6 -10 4-6.32639 39.1025 1
-6 -10 5 56.7462 43.0258 1
-6 -11 -8 125.165 67.9752 2
-6 -11 -7 85.8970 56.7380 2
-6 -11 -6 47.6055 48.0216 2
-6 -11 -5 23.4575 33.0839 2
-6 -11 -4 19.7118 40.1465 2
-6 -11 -3 43.2383 46.3038 1
-6 -11 -2 45.1057 40.4111 1
-6 -11 -1 71.7786 38.4546 1
-6 -11 0 236.704 72.7943 1
-6 -11 1 176.691 62.6495 1
-6 -11 2-16.2358 36.9747 1
-6 -12 -5 46.7381 40.1218 2
-6 -12 -4 88.1714 44.8884 2
-7 0 0-7.20954 29.8302 1
-7 0 -1 16.8183 28.8790 1
-7 0 -2 27.0774 24.3583 1
-7 0 -3-40.3481 32.7660 1
-7 0 -4-10.4243 26.6104 1
-7 0 -5 150.109 51.1161 1
-7 0 -6 18.0049 24.1125 1
-7 0 -7 40.4324 30.8796 1
-7 0 -8 83.8917 38.5443 1
-7 -1 -10 12.7486 24.1639 1
-7 -1 -9-107.405 43.5605 1
-7 -1 -8 50.5528 33.8786 1
-7 -1 -7 73.4860 41.2831 1
-7 -1 -6 79.5534 36.1451 1
-7 -1 -5 13.7438 32.7099 1
-7 -1 -4 32.9178 32.8337 1
-7 -1 -3 14.6311 26.8990 1
-7 -1 -2 183.649 57.9464 1
-7 -1 -1 57.9654 36.6898 1
-7 -1 0 2.62114 29.5249 1
-7 -1 1 55.7149 39.4283 1
-7 1 -1-0.58223 34.1197 1
-7 1 -2 66.1987 32.2760 1
-7 1 -3 36.0739 33.2841 1
-7 1 -4 11.0250 25.3110 1
-7 1 -5 15.7296 25.0377 1
-7 1 -6 133.192 43.7117 1
-7 -2 -10 38.3582 30.2438 1
-7 -2 -9-10.5586 34.0322 1
-7 -2 -8-32.0094 30.6988 1
-7 -2 -7 6.35498 25.8392 1
-7 -2 -6 212.597 61.1466 1
-7 -2 -5 55.5291 36.7133 1
-7 -2 -4 63.9703 39.5460 1
-7 -2 -3 9.33968 31.6188 1
-7 -2 -2 292.252 68.8518 1
-7 -2 -1 41.1765 35.7244 1
-7 -2 0 29.3234 30.1187 1
-7 -2 1 9.15543 28.1895 1
-7 2 -2 319.740 61.7985 1
-7 -3 -10 6.75103 23.0438 1
-7 -3 -9-48.4426 33.5265 1
-7 -3 -8 140.212 51.5532 1
-7 -3 -7 104.631 45.3869 1
-7 -3 -6-10.8557 27.1414 1
-7 -3 -5 248.261 65.1441 1
-7 -3 -4 766.453 106.873 1
-7 -3 -3 3.95357 32.4085 1
-7 -3 -2 44.7683 37.2671 1
-7 -3 -1 3.77408 37.3749 1
-7 -3 0-39.5479 41.9110 1
-7 -3 1-6.98017 33.2192 1
-7 -3 2 119.921 50.7565 1
-7 -4 -8-10.7828 28.7651 1
-7 -4 -7 116.887 47.7211 1
-7 -4 -6 111.049 54.3274 1
-7 -4 -5 189.630 61.3970 1
-7 -4 -4 151.619 54.9341 1
-7 -4 -4 63.0393 40.0388 2
-7 -4 -3 77.6557 39.6400 1
-7 -4 -3 78.5498 39.8140 2
-7 -4 -2 17.5141 35.7874 1
-7 -4 -1-3.93248 37.2423 1
-7 -4 0 253.625 66.0248 1
-7 -4 1-84.5565 45.2026 1
-7 -4 2 56.3796 39.1827 1
-7 -5 -7 14.8230 31.1098 1
-7 -5 -6 100.362 48.2464 1
-7 -5 -5 257.655 66.4714 2
-7 -5 -5 431.330 89.2363 1
-7 -5 -4 462.946 89.3092 1
-7 -5 -4 412.226 84.7785 2
-7 -5 -3 372.983 78.4281 1
-7 -5 -3 324.187 75.7485 2
-7 -5 -2 68.3693 44.0140 1
-7 -5 -1-92.2281 47.5955 1
-7 -5 0 69.1918 39.1362 1
-7 -5 1-98.1666 46.8690 1
-7 -5 2 37.6342 27.4283 1
-7 -5 3 312.723 79.1312 1
-7 -6 -6 145.951 55.5479 2
-7 -6 -5 169.710 61.4839 2
-7 -6 -5 162.674 58.6912 1
-7 -6 -4 77.8934 43.2658 1
-7 -6 -4 36.9128 33.3323 2
-7 -6 -3 109.286 52.7483 1
-7 -6 -3 33.4310 30.0666 2
-7 -6 -2 128.473 54.3514 1
-7 -6 -1 32.5040 27.1710 1
-7 -6 0 119.550 54.1404 1
-7 -6 1-64.4652 44.4412 1
-7 -6 2 44.8596 43.2631 1
-7 -6 3 95.4322 53.1554 1
-7 -7 -7 84.3779 45.2766 2
-7 -7 -6 79.5383 45.8178 2
-7 -7 -5 68.1295 33.4956 2
-7 -7 -4 63.2502 39.7524 2
-7 -7 -3-12.7936 27.0508 2
-7 -8 -7 33.5862 38.1185 2
-7 -8 -6 1.21018 33.2340 2
-7 -8 -5 93.3630 48.7320 2
-7 -8 -4 30.1119 32.9734 2
-7 -8 -3-31.2644 30.2599 2
-7 -9 -6 45.8543 51.6811 2
-7 -9 -5 0.31062 39.8622 2
-7 -9 -4 54.9782 53.9506 2
-7 -9 -3-17.5457 35.8096 2
0 0 0 0.00 0.00 0
TITL bmk1584 in P222(1)
REM P222(1) (#17 in standard setting)
CELL 0.71073 5.648679 16.747939 16.972626 90.0000 90.0000 90.0000
ZERR 4.00 0.000351 0.001106 0.001349 0.0000 0.0000 0.0000
LATT -1
SYMM -x,-y, z+1/2
SYMM -x, y,-z+1/2
SYMM x,-y,-z
SFAC C H N O S
UNIT 72.00 48.00 16.00 12.00 4.00
TREF
HKLF 4
END
;
_shelx_hkl_checksum 66458
_shelx_res_file
;
TITL SIR92 run in space group P 21 21 21
CELL 0.71073 5.6487 16.7479 16.9726 90.000 90.000 90.000
ZERR 4.00 0.0003 0.0011 0.0014 0.000 0.000 0.000
LATT -1
SYMM 1/2 - X, - Y, 1/2 + Z
SYMM 1/2 + X, 1/2 - Y, - Z
SYMM - X, 1/2 + Y, 1/2 - Z
SFAC C H N O S
UNIT 60 64 16 12 4
MERG 2
FMAP 2
PLAN 5
SIZE 0.114 0.179 0.182
ACTA
BOND $H
htab n2 o2
htab n4 o1
CONF
L.S. 5
TEMP 25.00
WGHT 0.054200 0.271800
FVAR 3.59874
C1 1 0.535730 -0.026808 0.381497 11.00000 0.05351 0.05310 =
0.04488 0.00473 0.00042 0.00726
C2 1 0.232321 -0.034880 0.460164 11.00000 0.05727 0.08183 =
0.05526 0.00436 0.00758 0.00917
AFIX 43
H2 2 0.097747 -0.057933 0.482049 11.00000 -1.20000
AFIX 0
C3 1 0.313590 0.035158 0.484543 11.00000 0.06927 0.07292 =
0.05659 -0.00139 0.01221 0.01652
AFIX 43
H3 2 0.245845 0.065677 0.524382 11.00000 -1.20000
AFIX 0
C4 1 0.879077 -0.009646 0.296331 11.00000 0.04924 0.04729 =
0.04323 0.00611 -0.00053 0.00532
C5 1 1.033140 -0.048595 0.237563 11.00000 0.05063 0.04633 =
0.04106 0.00314 0.00130 0.00364
C6 1 0.991500 -0.131553 0.211823 11.00000 0.06457 0.04706 =
0.05243 0.00161 0.00664 0.00129
C7 1 1.132840 -0.241640 0.138992 11.00000 0.09153 0.04912 =
0.08728 -0.01373 0.01266 0.00425
AFIX 23
H7A 2 1.087203 -0.273240 0.184415 11.00000 -1.20000
H7B 2 1.285542 -0.260736 0.120872 11.00000 -1.20000
AFIX 0
C8 1 0.958791 -0.252266 0.076782 11.00000 0.15364 0.07797 =
0.10866 -0.01656 -0.01509 -0.00566
AFIX 137
H8A 2 0.808098 -0.232535 0.094242 11.00000 -1.50000
H8B 2 0.945430 -0.307975 0.064231 11.00000 -1.50000
H8C 2 1.007904 -0.223304 0.030789 11.00000 -1.50000
AFIX 0
C9 1 1.459284 0.099002 0.185227 11.00000 0.04191 0.04758 =
0.04274 0.00344 -0.00387 0.00287
C10 1 1.486610 0.179442 0.199646 11.00000 0.05614 0.04882 =
0.06603 -0.00444 0.00127 0.00705
AFIX 43
H10 2 1.385603 0.205307 0.234588 11.00000 -1.20000
AFIX 0
C11 1 1.663987 0.221661 0.162214 11.00000 0.05590 0.04744 =
0.07503 0.00314 -0.00178 -0.00389
AFIX 43
H11 2 1.680689 0.276051 0.171754 11.00000 -1.20000
AFIX 0
C12 1 1.817278 0.183805 0.110598 11.00000 0.04488 0.07270 =
0.05528 0.01027 -0.00721 -0.00004
C13 1 1.788599 0.102718 0.098704 11.00000 0.04792 0.07565 =
0.05102 -0.00348 0.00161 0.00261
AFIX 43
H13 2 1.892288 0.076232 0.065111 11.00000 -1.20000
AFIX 0
C14 1 1.611836 0.060052 0.134929 11.00000 0.04850 0.05228 =
0.05095 -0.00483 -0.00268 0.00359
AFIX 43
H14 2 1.595361 0.005611 0.125630 11.00000 -1.20000
AFIX 0
C15 1 2.008037 0.230919 0.068319 11.00000 0.06018 0.09886 =
0.07841 0.02031 -0.00137 -0.01476
AFIX 137
H15A 2 2.160991 0.211667 0.084035 11.00000 -1.50000
H15B 2 1.994068 0.286410 0.081714 11.00000 -1.50000
H15C 2 1.989838 0.224514 0.012439 11.00000 -1.50000
AFIX 0
N1 3 0.357527 -0.071771 0.400718 11.00000 0.05897 0.06558 =
0.05207 0.00167 0.00796 -0.00055
N2 3 0.693425 -0.052178 0.324432 11.00000 0.05981 0.04908 =
0.05449 -0.00292 0.01098 0.00057
AFIX 43
H2A 2 0.671723 -0.099070 0.305087 11.00000 -1.20000
AFIX 0
N3 3 1.215312 -0.013220 0.204489 11.00000 0.05040 0.04428 =
0.04517 0.00199 -0.00262 0.00400
N4 3 1.269621 0.059639 0.222578 11.00000 0.04936 0.04567 =
0.05082 -0.00292 0.00509 0.00356
AFIX 43
H4 2 1.188717 0.084347 0.257905 11.00000 -1.20000
AFIX 0
O1 4 0.918913 0.058551 0.320868 11.00000 0.06268 0.04863 =
0.05493 -0.00469 0.00581 0.00130
O2 4 0.828333 -0.172290 0.234314 11.00000 0.08951 0.05079 =
0.09353 -0.01151 0.03489 -0.01453
O3 4 1.153371 -0.158504 0.162020 11.00000 0.07933 0.04616 =
0.07250 -0.00992 0.02112 -0.00034
S1 5 0.561518 0.061545 0.432180 11.00000 0.07563 0.05575 =
0.06563 -0.00675 0.01453 0.00354
HKLF 4
REM SIR92 run in space group P 21 21 21
REM R1 = 0.0477 for 2691 Fo > 4sig(Fo) and 0.0697 for all 3601 data
REM 210 parameters refined using 0 restraints
END
WGHT 0.0542 0.2718
REM Highest difference peak 0.176, deepest hole -0.188, 1-sigma level 0.042
Q1 1 1.2115 -0.2435 0.0616 11.00000 0.05 0.18
Q2 1 2.1370 0.2634 0.1365 11.00000 0.05 0.14
Q3 1 0.9806 -0.3218 0.0585 11.00000 0.05 0.14
Q4 1 0.8352 -0.2326 0.2050 11.00000 0.05 0.13
Q5 1 0.3668 -0.1240 0.3906 11.00000 0.05 0.13
;
_shelx_res_checksum 16716
_shelxl_version_number .2013
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_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
C C1 0.5357(7) -0.0268(2) 0.3815(2) 0.0505(8) Uani d 1
C C2 0.2323(7) -0.0349(3) 0.4602(2) 0.0648(11) Uani d 1
H H2 0.0977 -0.0579 0.4820 0.078 Uiso calc 1
C C3 0.3136(8) 0.0352(3) 0.4845(3) 0.0663(11) Uani d 1
H H3 0.2458 0.0657 0.5244 0.080 Uiso calc 1
C C4 0.8791(6) -0.0096(2) 0.2963(2) 0.0466(8) Uani d 1
C C5 1.0331(6) -0.0486(2) 0.2376(2) 0.0460(8) Uani d 1
C C6 0.9915(7) -0.1316(2) 0.2118(2) 0.0547(9) Uani d 1
C C7 1.1328(9) -0.2416(2) 0.1390(3) 0.0760(13) Uani d 1
H H7A 1.0872 -0.2732 0.1844 0.091 Uiso calc 1
H H7B 1.2855 -0.2607 0.1209 0.091 Uiso calc 1
C C8 0.9588(13) -0.2523(3) 0.0768(4) 0.113(2) Uani d 1
H H8A 0.8081 -0.2325 0.0942 0.170 Uiso calc 1
H H8B 0.9454 -0.3080 0.0642 0.170 Uiso calc 1
H H8C 1.0079 -0.2233 0.0308 0.170 Uiso calc 1
C C9 1.4593(6) 0.09900(19) 0.1852(2) 0.0441(7) Uani d 1
C C10 1.4866(7) 0.1794(2) 0.1996(2) 0.0570(9) Uani d 1
H H10 1.3856 0.2053 0.2346 0.068 Uiso calc 1
C C11 1.6640(7) 0.2217(2) 0.1622(3) 0.0595(10) Uani d 1
H H11 1.6807 0.2761 0.1718 0.071 Uiso calc 1
C C12 1.8173(6) 0.1838(2) 0.1106(2) 0.0576(10) Uani d 1
C C13 1.7886(7) 0.1027(2) 0.0987(2) 0.0582(10) Uani d 1
H H13 1.8923 0.0762 0.0651 0.070 Uiso calc 1
C C14 1.6118(6) 0.0601(2) 0.1349(2) 0.0506(8) Uani d 1
H H14 1.5954 0.0056 0.1256 0.061 Uiso calc 1
C C15 2.0080(7) 0.2309(3) 0.0683(3) 0.0792(13) Uani d 1
H H15A 2.1610 0.2117 0.0840 0.119 Uiso calc 1
H H15B 1.9941 0.2864 0.0817 0.119 Uiso calc 1
H H15C 1.9898 0.2245 0.0124 0.119 Uiso calc 1
N N1 0.3575(6) -0.07177(19) 0.40072(19) 0.0589(8) Uani d 1
N N2 0.6934(6) -0.05218(19) 0.32443(18) 0.0545(7) Uani d 1
H H2A 0.6717 -0.0991 0.3051 0.065 Uiso calc 1
N N3 1.2153(5) -0.01322(15) 0.20449(17) 0.0466(7) Uani d 1
N N4 1.2696(5) 0.05964(17) 0.22258(17) 0.0486(7) Uani d 1
H H4 1.1887 0.0843 0.2579 0.058 Uiso calc 1
O O1 0.9189(4) 0.05855(15) 0.32087(15) 0.0554(6) Uani d 1
O O2 0.8283(6) -0.17229(15) 0.2343(2) 0.0779(9) Uani d 1
O O3 1.1534(5) -0.15850(15) 0.16202(17) 0.0660(8) Uani d 1
S S1 0.5615(2) 0.06154(6) 0.43218(7) 0.0657(3) Uani 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 0.0535(19) 0.0531(18) 0.0449(19) 0.0073(18) 0.0004(17) 0.0047(16)
C2 0.057(2) 0.082(3) 0.055(2) 0.009(2) 0.0076(19) 0.004(2)
C3 0.069(2) 0.073(3) 0.057(2) 0.017(2) 0.012(2) -0.001(2)
C4 0.0492(19) 0.0473(18) 0.0432(19) 0.0053(15) -0.0005(16) 0.0061(16)
C5 0.0506(18) 0.0463(17) 0.0411(18) 0.0036(16) 0.0013(15) 0.0031(15)
C6 0.065(2) 0.0471(17) 0.052(2) 0.0013(18) 0.007(2) 0.0016(17)
C7 0.092(3) 0.049(2) 0.087(3) 0.004(2) 0.013(3) -0.014(2)
C8 0.154(5) 0.078(3) 0.109(4) -0.006(4) -0.015(5) -0.017(3)
C9 0.0419(16) 0.0476(16) 0.0427(18) 0.0029(15) -0.0039(15) 0.0034(15)
C10 0.056(2) 0.0488(18) 0.066(3) 0.0071(17) 0.001(2) -0.0044(18)
C11 0.056(2) 0.0474(19) 0.075(3) -0.0039(17) -0.002(2) 0.0031(19)
C12 0.0449(18) 0.073(2) 0.055(2) 0.0000(19) -0.0072(19) 0.010(2)
C13 0.048(2) 0.076(2) 0.051(2) 0.0026(19) 0.0016(18) -0.0035(19)
C14 0.0485(18) 0.0523(19) 0.051(2) 0.0036(17) -0.0027(16) -0.0048(18)
C15 0.060(2) 0.099(3) 0.078(3) -0.015(2) -0.001(2) 0.020(3)
N1 0.0590(18) 0.066(2) 0.0521(18) -0.0005(16) 0.0080(16) 0.0017(16)
N2 0.0598(17) 0.0491(15) 0.0545(18) 0.0006(15) 0.0110(15) -0.0029(14)
N3 0.0504(16) 0.0443(14) 0.0452(16) 0.0040(13) -0.0026(14) 0.0020(13)
N4 0.0494(15) 0.0457(14) 0.0508(17) 0.0036(14) 0.0051(13) -0.0029(14)
O1 0.0627(15) 0.0486(13) 0.0549(15) 0.0013(13) 0.0058(12) -0.0047(12)
O2 0.090(2) 0.0508(14) 0.094(2) -0.0145(15) 0.035(2) -0.0115(15)
O3 0.0793(18) 0.0462(13) 0.0725(19) -0.0003(13) 0.0211(16) -0.0099(13)
S1 0.0756(6) 0.0558(5) 0.0656(6) 0.0035(5) 0.0145(5) -0.0067(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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 N2 119.8(3)
N1 C1 S1 116.1(3)
N2 C1 S1 124.1(3)
C3 C2 N1 116.6(4)
C3 C2 H2 121.7
N1 C2 H2 121.7
C2 C3 S1 110.4(3)
C2 C3 H3 124.8
S1 C3 H3 124.8
O1 C4 N2 120.5(3)
O1 C4 C5 121.9(3)
N2 C4 C5 117.5(3)
N3 C5 C6 115.0(3)
N3 C5 C4 123.5(3)
C6 C5 C4 121.5(3)
O2 C6 O3 122.4(3)
O2 C6 C5 124.0(3)
O3 C6 C5 113.6(3)
O3 C7 C8 111.5(4)
O3 C7 H7A 109.3
C8 C7 H7A 109.3
O3 C7 H7B 109.3
C8 C7 H7B 109.3
H7A C7 H7B 108.0
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C14 C9 C10 120.2(3)
C14 C9 N4 122.2(3)
C10 C9 N4 117.6(3)
C9 C10 C11 120.0(4)
C9 C10 H10 120.0
C11 C10 H10 120.0
C10 C11 C12 120.7(4)
C10 C11 H11 119.7
C12 C11 H11 119.7
C13 C12 C11 117.9(4)
C13 C12 C15 121.7(4)
C11 C12 C15 120.4(4)
C14 C13 C12 122.1(4)
C14 C13 H13 119.0
C12 C13 H13 119.0
C13 C14 C9 119.1(4)
C13 C14 H14 120.5
C9 C14 H14 120.5
C12 C15 H15A 109.5
C12 C15 H15B 109.5
H15A C15 H15B 109.5
C12 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C1 N1 C2 108.8(3)
C4 N2 C1 125.7(3)
C4 N2 H2A 117.1
C1 N2 H2A 117.1
N4 N3 C5 120.6(3)
N3 N4 C9 121.0(3)
N3 N4 H4 119.5
C9 N4 H4 119.5
C6 O3 C7 116.3(3)
C3 S1 C1 88.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.299(5)
C1 N2 1.383(5)
C1 S1 1.718(4)
C2 C3 1.326(6)
C2 N1 1.378(5)
C2 H2 0.9300
C3 S1 1.717(4)
C3 H3 0.9300
C4 O1 1.236(4)
C4 N2 1.354(4)
C4 C5 1.476(5)
C5 N3 1.313(4)
C5 C6 1.475(5)
C6 O2 1.209(4)
C6 O3 1.325(4)
C7 O3 1.451(4)
C7 C8 1.454(7)
C7 H7A 0.9700
C7 H7B 0.9700
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 C14 1.377(5)
C9 C10 1.378(5)
C9 N4 1.409(4)
C10 C11 1.381(5)
C10 H10 0.9300
C11 C12 1.385(6)
C11 H11 0.9300
C12 C13 1.382(5)
C12 C15 1.516(5)
C13 C14 1.373(5)
C13 H13 0.9300
C14 H14 0.9300
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
N2 H2A 0.8600
N3 N4 1.295(4)
N4 H4 0.8600
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
N2 H2A O2 . 0.86 1.93 2.639(4) 139
N4 H4 O1 . 0.86 1.91 2.590(4) 135
C10 H10 O2 4_755 0.93 2.44 3.255(5) 147
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
N1 C2 C3 S1 0.5(5)
O1 C4 C5 N3 -3.2(5)
N2 C4 C5 N3 178.4(3)
O1 C4 C5 C6 176.7(3)
N2 C4 C5 C6 -1.7(5)
N3 C5 C6 O2 -177.8(4)
C4 C5 C6 O2 2.3(6)
N3 C5 C6 O3 3.3(5)
C4 C5 C6 O3 -176.6(3)
C14 C9 C10 C11 1.5(5)
N4 C9 C10 C11 -177.5(3)
C9 C10 C11 C12 -0.6(6)
C10 C11 C12 C13 -0.8(6)
C10 C11 C12 C15 178.6(4)
C11 C12 C13 C14 1.4(6)
C15 C12 C13 C14 -178.0(4)
C12 C13 C14 C9 -0.5(5)
C10 C9 C14 C13 -0.9(5)
N4 C9 C14 C13 178.0(3)
N2 C1 N1 C2 178.0(3)
S1 C1 N1 C2 -0.6(4)
C3 C2 N1 C1 0.0(5)
O1 C4 N2 C1 -0.9(5)
C5 C4 N2 C1 177.6(3)
N1 C1 N2 C4 176.6(3)
S1 C1 N2 C4 -4.9(5)
C6 C5 N3 N4 -179.8(3)
C4 C5 N3 N4 0.1(5)
C5 N3 N4 C9 -177.6(3)
C14 C9 N4 N3 -7.5(5)
C10 C9 N4 N3 171.5(3)
O2 C6 O3 C7 -3.4(6)
C5 C6 O3 C7 175.5(3)
C8 C7 O3 C6 81.4(5)
C2 C3 S1 C1 -0.7(3)
N1 C1 S1 C3 0.8(3)
N2 C1 S1 C3 -177.8(3)
_cod_database_fobs_code 1548669