#------------------------------------------------------------------------------
#$Date: 2023-09-20 04:48:29 +0300 (Wed, 20 Sep 2023) $
#$Revision: 286428 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/28/2022863.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_2022863
loop_
_publ_author_name
'Sakamoto, Nasa'
'Gato, Katsuhiko'
_publ_section_title
;
Crystal structure of a 1:1 co-crystal of quabodepistat (OPC-167832) with
2,5-dihydroxybenzoic acid using microcrystal electron diffraction
;
_journal_coeditor_code DJ2052
_journal_issue 10
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi 10.1107/S2056989023006047
_journal_volume 79
_journal_year 2023
_chemical_formula_iupac 'C21 H20 Cl F3 N2 O4, C7 H6 O4'
_chemical_formula_moiety 'C21 H20 Cl F3 N2 O4, C7 H6 O4'
_chemical_formula_sum 'C28 H26 Cl F3 N2 O8'
_chemical_formula_weight 610.96
_chemical_name_common quabodepistat-2,5-dihydroxybenzoicacid
_chemical_name_systematic
'5-{[(3R,4R)-1-(4-Chloro-2,6-difluorophenyl)-3,4-dihydroxypiperidin-4-yl]methoxy}-8-fluoro-3,4-dihydroquinolin-2(1H)-one--2,5-dihydroxybenzoic acid (1/1)'
_space_group_crystal_system monoclinic
_space_group_IT_number 4
_space_group_name_Hall 'P 2yb'
_space_group_name_H-M_alt 'P 1 21 1'
_atom_sites_solution_hydrogens geom
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_cell_angle_alpha 90
_cell_angle_beta 90.30(9)
_cell_angle_gamma 90
_cell_formula_units_Z 2
_cell_length_a 5.6(3)
_cell_length_b 9.6(3)
_cell_length_c 28.2(3)
_cell_measurement_reflns_used 411
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 0.8340
_cell_measurement_theta_min 0.1030
_cell_volume 1516(10)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2022)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2022)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2022)
;
_computing_molecular_graphics
;
Olex2 1.5 (Dolomanov et al., 2009)
;
_computing_publication_material
;
Olex2 1.5 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXD (Sheldrick, 2008)
;
_diffrn_ambient_temperature 293(2)
_diffrn_detector 'HPC area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.931
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type 'Rigaku XtaLAB Synergy-ED'
_diffrn_measurement_method rotation
_diffrn_radiation_type electron
_diffrn_radiation_wavelength 0.0251
_diffrn_reflns_av_R_equivalents 0.1491
_diffrn_reflns_av_unetI/netI 0.1595
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_h_min -6
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 31
_diffrn_reflns_limit_l_min -31
_diffrn_reflns_number 8548
_diffrn_reflns_theta_full 0.799
_diffrn_reflns_theta_max 0.799
_diffrn_reflns_theta_min 0.107
_diffrn_source 'thermionic-emission electron gun'
_exptl_absorpt_coefficient_mu 0.000
_exptl_absorpt_correction_type none
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.338
_exptl_crystal_description 'thin platelets'
_exptl_crystal_F_000 224
_exptl_crystal_size_max 1
_exptl_crystal_size_mid 0.2
_exptl_crystal_size_min 0.2
_refine_diff_density_max 0.149
_refine_diff_density_min -0.146
_refine_ls_abs_structure_details
;
All f" are zero, so absolute structure could not be determined
;
_refine_ls_extinction_coef 37E1(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
'SHELXL2018/3 (Sheldrick, 2015)'
;
_refine_ls_goodness_of_fit_ref 1.075
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 348
_refine_ls_number_reflns 4096
_refine_ls_number_restraints 537
_refine_ls_restrained_S_all 1.034
_refine_ls_R_factor_all 0.2455
_refine_ls_R_factor_gt 0.1602
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2805P)^2^+0.1700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.4121
_refine_ls_wR_factor_ref 0.4803
_reflns_number_gt 2030
_reflns_number_total 4096
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file dj2052sup1.cif
_cod_data_source_block I
_cod_original_cell_volume 152E1(11)
_cod_database_code 2022863
_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_hkl_file
;
0 -10 0 74.7904 32.5314 1
0 -10 -1 44.8843 28.5421 1
0 -10 1-1.15184 27.4757 1
0 -10 2 38.1195 32.9666 1
0 -10 -2 6.97725 28.7914 1
0 -10 -3-12.9031 25.1940 1
0 -10 3 66.2080 34.3614 1
0 -10 4 26.7980 36.7098 1
0 -10 -4 20.4311 26.8364 1
0 -10 5 15.6967 38.6725 1
0 -10 -5 39.3686 28.6215 1
0 -10 -6 11.4919 27.3159 1
0 -10 6-20.2142 33.7692 1
0 -10 -7 12.6185 28.2392 1
0 -10 -7 113.844 100.546 1
0 -10 7-2.87347 32.6996 1
0 -10 -8 8.98354 27.0906 1
0 -10 -8-103.533 83.6669 1
0 -10 8-26.4626 33.9091 1
0 -10 9-9.44596 35.1678 1
0 -10 -9-48.8766 24.6007 1
0 -10 -9 67.4037 93.3232 1
0 -10 -10-6.43736 24.8161 1
0 -10 10-10.0123 36.2539 1
0 -10 -10-150.647 87.7776 1
0 -10 11 73.4036 40.9500 1
0 -10 -11 41.5215 81.4841 1
0 -10 -11 37.0988 24.8396 1
0 -9 0 114.182 39.7526 1
0 -9 -1 99.6117 35.8312 1
0 -9 1 69.2139 36.3621 1
0 -9 2 33.7534 40.2863 1
0 -9 -2 64.3522 35.8537 1
0 -9 -3 20.6116 32.9043 1
0 -9 3 94.9681 45.2248 1
0 -9 4 54.5559 45.4944 1
0 -9 -4 31.7962 38.1664 1
0 -9 -5 18.5970 35.3694 1
0 -9 5 158.839 49.7486 1
0 -9 -6-16.7115 101.981 1
0 -9 6 51.5775 42.4193 1
0 -9 -6 129.999 37.7440 1
0 -9 -7-3.41333 100.795 1
0 -9 -7 37.3018 35.9287 1
0 -9 7 2.73783 41.6114 1
0 -9 -8-17.5200 98.9219 1
0 -9 8 17.7709 42.3033 1
0 -9 -8-6.68757 32.8947 1
0 -9 9 67.5498 47.5189 1
0 -9 -9-10.1348 91.7125 1
0 -9 -9 90.1897 33.8339 1
0 -9 -10 227.470 34.8437 1
0 -9 10 250.212 52.3830 1
0 -9 -10 226.058 96.1285 1
0 -9 -11 293.735 36.3549 1
0 -9 11 260.037 57.1291 1
0 -9 -11 295.820 101.269 1
0 -9 12 89.8615 57.9094 1
0 -9 -12 251.095 103.550 1
0 -9 -12 67.8706 35.7489 1
0 -9 -13 150.465 36.5142 1
0 -9 13 204.548 62.6156 1
0 -9 -13 334.421 103.864 1
0 -9 -14 186.116 99.5505 1
0 -9 -14 143.764 34.9811 1
0 -9 14 181.250 62.2429 1
0 -9 15-52.7367 55.1859 1
0 -9 -15 79.3419 33.8679 1
0 -9 -15 26.4568 91.5428 1
0 -9 -16 48.5794 33.0333 1
0 -9 16 48.2211 59.6284 1
0 -9 -16-72.0315 89.0207 1
0 -8 0 536.592 51.6426 1
0 -8 -1 309.593 46.7276 1
0 -8 1 329.188 45.2736 1
0 -8 -2 135.360 45.3801 1
0 -8 2 112.984 48.8728 1
0 -8 -3 94.5969 41.0040 1
0 -8 3 107.110 51.7706 1
0 -8 4 128.642 53.5769 1
0 -8 -4 193.351 45.4714 1
0 -8 -5 165.447 45.3357 1
0 -8 5 103.870 48.1349 1
0 -8 -5 88.9031 105.572 1
0 -8 6 135.277 47.3723 1
0 -8 -6 366.303 47.0876 1
0 -8 -6 370.573 111.677 1
0 -8 -7 389.077 117.136 1
0 -8 7 355.470 55.7605 1
0 -8 -7 465.524 48.3343 1
0 -8 -8 1282.54 126.017 1
0 -8 8 943.873 67.3413 1
0 -8 -8 1232.52 55.3168 1
0 -8 -9 1063.28 121.018 1
0 -8 -9 896.377 47.5995 1
0 -8 9 849.274 68.4390 1
0 -8 -10 330.706 117.626 1
0 -8 10 371.396 66.2042 1
0 -8 -10 385.274 46.5028 1
0 -8 -11 251.267 46.2175 1
0 -8 -11 301.874 114.437 1
0 -8 11 70.5327 64.9259 1
0 -8 -12 110.516 43.1711 1
0 -8 -12 121.467 114.128 1
0 -8 12 61.4961 66.9276 1
0 -8 -13-94.0808 102.821 1
0 -8 13 72.7054 69.2919 1
0 -8 -13 101.619 42.1528 1
0 -8 -14-20.2633 38.1831 1
0 -8 14 74.7031 67.5715 1
0 -8 -14 55.8488 99.9690 1
0 -8 -15 20.0728 99.3958 1
0 -8 15-84.4950 67.4666 1
0 -8 -16-23.8906 89.6562 1
0 -8 16-88.4906 63.9099 1
0 -8 -17 28.1562 89.7615 1
0 -8 17-2.46430 63.6916 1
0 -8 18 38.1721 61.1517 1
0 -8 -18 40.5130 84.4965 1
0 -8 19 64.9039 58.2903 1
0 -8 -19 32.2635 81.8596 1
0 -8 -20 107.909 79.1835 1
0 -7 0 188.862 48.5270 1
0 -7 -1 85.9435 44.2439 1
0 -7 1 115.843 47.1450 1
0 -7 -2 126.416 44.1345 1
0 -7 2 231.047 51.9032 1
0 -7 -3 103.450 46.0587 1
0 -7 3 288.590 57.3749 1
0 -7 -4 892.984 55.3156 1
0 -7 4 730.261 57.2510 1
0 -7 5 298.590 51.4843 1
0 -7 -5 335.103 50.3544 1
0 -7 -5 233.905 107.711 1
0 -7 6 337.297 55.2110 1
0 -7 -6 579.305 119.267 1
0 -7 7 329.925 58.8118 1
0 -7 -7 470.014 109.828 1
0 -7 -7 420.789 48.0799 1
0 -7 -8 245.824 104.867 1
0 -7 -8 332.477 42.9320 1
0 -7 8 411.589 62.5158 1
0 -7 9 113.261 64.1111 1
0 -7 -9 119.427 112.305 1
0 -7 -9 104.770 46.3051 1
0 -7 -10 64.2697 48.5472 1
0 -7 10 141.281 72.5780 1
0 -7 -10 210.592 120.676 1
0 -7 11 51.1658 73.7115 1
0 -7 -11 99.4102 116.651 1
0 -7 -11 31.5211 46.9599 1
0 -7 12 179.351 79.6698 1
0 -7 -12 59.8030 111.299 1
0 -7 -12 123.062 46.2695 1
0 -7 13-8.61892 79.9576 1
0 -7 -13 106.562 45.2773 1
0 -7 -13 83.6701 109.081 1
0 -7 14 354.317 82.6958 1
0 -7 -14-13.9128 98.7463 1
0 -7 -15 73.2081 95.5980 1
0 -7 15 56.4426 76.0424 1
0 -7 -16 170.653 91.1514 1
0 -7 16 19.2049 70.0939 1
0 -7 17 159.355 70.3302 1
0 -7 -17-53.0603 83.9330 1
0 -7 -18-3.64382 87.2235 1
0 -7 -19-49.1491 84.5390 1
0 -7 -20 19.8563 84.5233 1
0 -7 -21 70.0832 82.2445 1
0 -7 -22 169.886 85.6461 1
0 -7 -23-142.625 81.9318 1
0 -6 0 2859.33 76.7963 1
0 -6 1 784.338 57.7958 1
0 -6 -1 922.649 58.2262 1
0 -6 2 407.186 59.4137 1
0 -6 -2 381.605 49.2717 1
0 -6 3 421.128 60.2073 1
0 -6 -3 381.250 55.5450 1
0 -6 -4 312.957 112.395 1
0 -6 4 305.506 50.0443 1
0 -6 -4 222.585 51.1000 1
0 -6 -5 302.358 50.2479 1
0 -6 5 270.278 53.4224 1
0 -6 -6 410.256 46.3192 1
0 -6 -6 614.660 110.441 1
0 -6 6 248.794 55.5407 1
0 -6 7 459.793 60.4174 1
0 -6 -7 254.169 101.036 1
0 -6 -8 621.583 53.6058 1
0 -6 -8 581.835 110.756 1
0 -6 8 357.043 69.9526 1
0 -6 -9 200.927 49.0183 1
0 -6 -9 129.545 102.954 1
0 -6 9 220.484 71.3587 1
0 -6 -10 218.882 47.8214 1
0 -6 -10 238.644 105.424 1
0 -6 10 200.703 74.4791 1
0 -6 -11 395.326 106.736 1
0 -6 11 144.778 79.5943 1
0 -6 -11 410.196 50.8901 1
0 -6 -12 526.997 106.730 1
0 -6 12 323.411 82.5760 1
0 -6 -13 63.3362 102.854 1
0 -6 13 228.303 80.5827 1
0 -6 -14 18.0109 93.6354 1
0 -6 14 61.8090 76.8843 1
0 -6 -15 184.949 98.5731 1
0 -6 -16 51.1781 97.4927 1
0 -6 -17 73.3912 97.8865 1
0 -6 -18 279.755 100.516 1
0 -6 -19 296.213 103.435 1
0 -6 -20 156.877 104.603 1
0 -6 -21 70.6231 102.950 1
0 -6 -22 49.5187 89.6517 1
0 -6 -23 132.395 70.2885 1
0 -6 -24 108.334 65.2452 1
0 -6 -25-31.0955 55.4513 1
0 -5 0 938.575 65.2989 1
0 -5 -1 319.480 56.4624 1
0 -5 1 764.318 63.2510 1
0 -5 2 1341.75 71.7056 1
0 -5 -2 1677.84 66.1796 1
0 -5 3 258.694 57.9698 1
0 -5 -3 345.087 59.4597 1
0 -5 -3 349.733 104.929 1
0 -5 -4 252.164 55.8472 1
0 -5 -4 140.806 107.553 1
0 -5 4 98.8949 53.3377 1
0 -5 -5 1870.98 116.736 1
0 -5 -5 1864.76 62.0556 1
0 -5 -6 377.941 50.8312 1
0 -5 6 333.260 67.0148 1
0 -5 7 549.007 76.5933 1
0 -5 -7 787.565 113.851 1
0 -5 -8 306.252 109.146 1
0 -5 8 283.694 76.1860 1
0 -5 -8 312.791 53.1665 1
0 -5 -9 111.594 49.5238 1
0 -5 9 188.154 77.4067 1
0 -5 -9 147.430 104.032 1
0 -5 -10 305.304 97.1531 1
0 -5 10 189.559 79.6040 1
0 -5 -11 516.942 97.3466 1
0 -5 11 360.514 75.6318 1
0 -5 -12 347.107 92.5302 1
0 -5 12 406.325 77.2776 1
0 -5 -13 996.637 100.796 1
0 -5 -14 597.224 96.8581 1
0 -5 -15 268.360 95.1263 1
0 -5 -16 165.899 100.823 1
0 -5 -17-57.9133 101.745 1
0 -5 -18 358.073 109.201 1
0 -5 -19 53.0416 82.6257 1
0 -5 -20 53.0038 73.7306 1
0 -5 -21 159.869 71.7741 1
0 -5 22-98.4590 156.526 1
0 -5 -22 111.777 84.0744 1
0 -5 23 232.366 152.262 1
0 -5 -23 78.2712 91.3630 1
0 -5 -24-4.38953 92.1802 1
0 -5 24-48.8455 128.433 1
0 -5 25-258.012 113.645 1
0 -5 -25-4.66308 87.6114 1
0 -5 26-174.335 114.426 1
0 -5 -26 54.5644 95.8012 1
0 -5 27-11.4261 108.699 1
0 -5 -27 141.725 92.8659 1
0 -4 0 2478.05 71.6536 1
0 -4 1 1977.69 71.4633 1
0 -4 -1 678.391 60.4816 1
0 -4 2 4747.44 91.0353 1
0 -4 -2 7379.15 99.0863 1
0 -4 -3 1054.94 64.5884 1
0 -4 -3 169.551 102.070 1
0 -4 -4 738.040 55.1025 1
0 -4 -4 767.599 109.739 1
0 -4 4 552.959 63.8712 1
0 -4 -5 3758.03 70.7511 1
0 -4 -5 5553.40 146.360 1
0 -4 6 671.411 86.0419 1
0 -4 -6 547.922 61.2295 1
0 -4 -6 460.624 119.604 1
0 -4 -7 636.490 60.4564 1
0 -4 7 572.485 89.1886 1
0 -4 -7 953.733 121.887 1
0 -4 8 1038.90 95.8801 1
0 -4 -8 1081.07 112.228 1
0 -4 9 684.132 86.8461 1
0 -4 -9 846.861 104.962 1
0 -4 -10 543.849 96.4676 1
0 -4 -11 252.086 89.9249 1
0 -4 -12 501.587 93.5402 1
0 -4 -13 261.823 97.9899 1
0 -4 -14 2.80767 94.6314 1
0 -4 -15 320.170 84.2210 1
0 -4 -16 215.315 68.3839 1
0 -4 -18 139.986 85.6677 1
0 -4 18 179.901 181.546 1
0 -4 -19 131.266 106.861 1
0 -4 19 313.557 179.248 1
0 -4 -20 123.388 111.855 1
0 -4 20 388.554 164.221 1
0 -4 -21 140.795 112.742 1
0 -4 21 90.0931 154.270 1
0 -4 -22-33.5727 110.952 1
0 -4 22 291.552 153.193 1
0 -4 23 15.4587 137.400 1
0 -4 -23 103.055 115.806 1
0 -4 24-52.0214 133.443 1
0 -4 -24 472.283 122.650 1
0 -4 -25 343.908 119.895 1
0 -4 25 167.338 131.878 1
0 -4 -26 374.995 123.446 1
0 -4 26 142.061 117.651 1
0 -4 -27 227.609 110.777 1
0 -4 27 84.9855 107.157 1
0 -4 28 72.9218 108.480 1
0 -4 -28-90.0700 99.2134 1
0 -4 29-145.950 109.631 1
0 -4 -29 63.5430 102.065 1
0 -3 0 2556.88 69.1437 1
0 -3 1 2945.82 73.6722 1
0 -3 -1 469.291 55.4035 1
0 -3 -2 2799.69 69.3443 1
0 -3 -2 2010.60 111.583 1
0 -3 3 168.660 55.8232 1
0 -3 -3 19.3728 92.2562 1
0 -3 -3 63.0405 47.9008 1
0 -3 4 1257.69 74.8195 1
0 -3 -4 1455.00 62.3541 1
0 -3 -4 1684.30 108.706 1
0 -3 5 1118.86 82.1770 1
0 -3 -5 1179.84 58.8770 1
0 -3 6 1539.28 91.2727 1
0 -3 -6 2707.54 111.315 1
0 -3 -7 665.758 90.9381 1
0 -3 7 1053.17 84.5458 1
0 -3 -8 3328.48 114.995 1
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0 -3 -10 4742.70 145.911 1
0 -3 -11 3036.08 116.479 1
0 -3 -12 601.354 77.3900 1
0 -3 -13 2378.97 107.835 1
0 -3 13 2099.69 217.821 1
0 -3 -14 530.869 101.536 1
0 -3 14 925.218 192.956 1
0 -3 -15 610.394 108.502 1
0 -3 15 240.139 168.232 1
0 -3 16 147.378 157.103 1
0 -3 -16 435.076 105.420 1
0 -3 17 42.5387 149.915 1
0 -3 -17 218.535 107.984 1
0 -3 18 390.388 153.303 1
0 -3 -18 258.199 111.544 1
0 -3 19 420.704 149.867 1
0 -3 -19 147.147 115.678 1
0 -3 20 346.676 147.253 1
0 -3 -20 309.221 128.148 1
0 -3 21-4.63106 148.700 1
0 -3 -21 240.242 136.672 1
0 -3 22 317.412 163.492 1
0 -3 -22 164.369 140.103 1
0 -3 -23 386.854 145.698 1
0 -3 23 300.448 164.245 1
0 -3 -24-64.3239 133.793 1
0 -3 24 301.226 158.073 1
0 -3 -25 260.345 137.590 1
0 -3 25 54.5271 156.353 1
0 -3 26 80.5829 147.992 1
0 -3 -26-18.0035 134.859 1
0 -3 27 25.6437 136.599 1
0 -3 -27 125.272 127.906 1
0 -3 -28-6.59221 120.657 1
0 -3 28 13.0454 122.724 1
0 -3 -29-145.827 114.526 1
0 -3 29-127.076 108.671 1
0 -3 30 224.264 127.311 1
0 -3 -30-146.023 114.047 1
0 -2 0 13973.4 98.0155 1
0 -2 -1 48377.4 162.079 1
0 -2 1 47687.1 160.972 1
0 -2 -2 527.246 56.8609 1
0 -2 -2 856.589 109.292 1
0 -2 2 806.306 65.9574 1
0 -2 -3 3865.03 131.794 1
0 -2 3 3522.61 96.3244 1
0 -2 -4 8273.91 137.709 1
0 -2 4 8130.22 119.854 1
0 -2 -5 4493.54 112.029 1
0 -2 -6 3225.67 102.853 1
0 -2 -7 516.910 85.5244 1
0 -2 -8 2868.27 84.8852 1
0 -2 -9 10874.2 155.156 1
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-6 2 -5 221.408 79.6923 1
0 0 0 0.00 0.00 0
TITL merge_2254_2260 in P2(1)
REM P2(1) (#4 in standard setting)
CELL 0.02510 5.594063 9.622357 28.161983 90.0000 90.2989 90.0000
ZERR 2.00 0.346651 0.326078 0.337047 0.0000 0.0939 0.0000
LATT -1
SYMM -x, y+1/2,-z
REM SFAC C H N O
SFAC C 0.731 36.995 1.195 11.297 0.456 2.814 0.125 0.346 0 0 0 0 0.77 12.011
SFAC H 0.375 15.495 0.141 4.126 0.022 0.025 -0.101 46.884 0 0 0 0 0.32 1.008
SFAC N 0.572 28.846 1.043 9.054 0.465 2.421 0.131 0.317 0 0 0 0 0.75 14.007
SFAC O 0.455 23.780 0.917 7.622 0.472 2.144 0.138 0.296 0 0 0 0 0.73 15.999
UNIT 52.00 52.00 4.00 16.00
TREF
HKLF 4
END
;
_shelx_hkl_checksum 14713
_shelx_res_file
;
TITL merge_2254_2260 in P21 #4
i.res
created by SHELXL-2018/3 at 16:11:44 on 15-Jul-2023
REM Best SHELXD solution FINAL CC 68.76
REM Fragments: 45 3
REM reset to P21 #4
REM WGHT 0.200000
CELL 0.0251 5.594063 9.622357 28.161983 90 90.2989 90
ZERR 2 0.346651 0.326078 0.337047 0 0.0939 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C 0.731 36.995 1.195 11.297 0.456 2.814 0.125 0.346 0 0 0 0 0.77 12.011
SFAC H 0.375 15.495 0.141 4.126 0.022 0.025 -0.101 46.884 0 0 0 0 0.32 1.008
SFAC Cl 0.340 0.338 0.891 2.619 2.388 11.068 1.238 33.538 0 0 0 0 0.99 17
SFAC F 0.152 0.289 0.519 2.062 0.822 7.263 0.308 22.026 0 0 0 0 0.64 9
SFAC N 0.572 28.846 1.042 9.054 0.465 2.421 0.131 0.317 0 0 0 0 0.75 14.007
SFAC O 0.455 23.78 0.917 7.622 0.472 2.144 0.138 0.296 0 0 0 0 0.73 15.999
UNIT 56 52 2 6 4 16
EQIV $1 1+X,-1+Y,+Z
EQIV $2 -1+X,1+Y,+Z
EQIV $3 -1+X,+Y,+Z
EQIV $4 1-X,0.5+Y,2-Z
EQIV $5 1+X,+Y,+Z
EQIV $6 1-X,-0.5+Y,2-Z
SIMU 0.01 0.02 2
DFIX 1.54 0.01 C15 C16 C16 C17 C15 C20 C20 C19 C9 C8 C9 C10 C11 C10 C32 C38
DFIX 1.43 0.01 O41 C33 O21 C16
DFIX 1.47 0.01 C17 N18 C19 N18
DFIX 1.76 0.01 Cl31 C26
SADI 0.01 C25 Cl31 C27 Cl31
SADI 0.01 C16 C20 C17 C19
FLAT C32 C33 C34 C35 C36 C37 C38 O39 O40 O41 O42
FLAT F29 C23 C28 F30 C27 C26 Cl31 C25 C24
RIGU C2 C3 C4 C5 C6 N7 C8 C9 C10 C11 O12 F13
RIGU C14 C15 C16 C17 N18 C19 C20 O21 O22
RIGU C32 C33 C34 C35 C36 C37 C38 O39 O40 O41 O42
L.S. 20 0 0
PLAN 4
CONF
HTAB C3 O42_$5
HTAB C9 O22_$2
HTAB N7 O40_$2
HTAB C34 O42_$6
HTAB O42 O41_$4
HTAB O39 O12_$1
HTAB O21 O22_$3
HTAB O22 O12_$1
LIST 4
MORE -1
BOND $H
fmap 2 53
acta
TWIN -1 0 0 0 -1 0 0 0 1 2
REM
REM
REM
WGHT 0.280500 0.170000
EXTI 367.920532
BASF 0.25311
FVAR 6.01960
AFIX 66
C2 1 0.960174 0.558920 0.794472 11.00000 0.07831 0.05728 =
0.07584 0.00533 0.00998 0.02947
C11 1 0.803926 0.670009 0.788639 11.00000 0.08499 0.05585 =
0.06222 0.01115 0.00825 0.03000
C6 1 0.660290 0.712101 0.826110 11.00000 0.08700 0.04258 =
0.05905 0.01466 0.00931 0.03378
C5 1 0.672900 0.643105 0.869414 11.00000 0.08804 0.06253 =
0.06586 0.02407 0.00710 0.03677
C4 1 0.829147 0.532016 0.875247 11.00000 0.08071 0.06868 =
0.07447 0.02013 0.00228 0.03740
AFIX 43
H4 2 0.837583 0.485853 0.904220 11.00000 -1.20000
AFIX 65
C3 1 0.972784 0.489923 0.837777 11.00000 0.08239 0.05932 =
0.07613 0.00770 0.00250 0.03209
AFIX 43
H3 2 1.077324 0.415597 0.841680 11.00000 -1.20000
AFIX 0
C10 1 0.796438 0.752693 0.741616 11.00000 0.08912 0.05771 =
0.06003 0.01052 0.00892 0.03108
AFIX 23
H10A 2 0.957975 0.785032 0.735893 11.00000 -1.20000
H10B 2 0.759602 0.686397 0.716684 11.00000 -1.20000
AFIX 0
C9 1 0.631204 0.877616 0.733804 11.00000 0.09635 0.06711 =
0.06199 0.01793 0.01464 0.03984
AFIX 23
H9A 2 0.528342 0.859999 0.706630 11.00000 -1.20000
H9B 2 0.726751 0.959210 0.726908 11.00000 -1.20000
AFIX 0
C8 1 0.476099 0.905902 0.777814 11.00000 0.09008 0.05844 =
0.05496 0.01318 0.01109 0.04451
N7 5 0.478811 0.824299 0.820633 11.00000 0.09643 0.04544 =
0.05930 0.00950 0.01502 0.03969
AFIX 43 1.0100
H7 2 0.359249 0.842859 0.846624 11.00000 -1.20000
AFIX 66
C32 1 0.785469 0.055173 0.917064 11.00000 0.05140 0.04986 =
0.05722 -0.00194 0.00156 0.00519
C37 1 0.610958 0.150027 0.903314 11.00000 0.05471 0.05188 =
0.05537 -0.00412 0.00778 0.01037
AFIX 43
H37 2 0.608891 0.184541 0.872468 11.00000 -1.20000
AFIX 65
C36 1 0.439537 0.193296 0.935665 11.00000 0.04910 0.06355 =
0.05860 -0.00360 0.00378 0.01517
C35 1 0.442625 0.141711 0.981767 11.00000 0.05207 0.06315 =
0.06166 0.00321 0.00860 0.00100
AFIX 43
H35 2 0.327933 0.170661 1.003412 11.00000 -1.20000
AFIX 65
C34 1 0.617135 0.046856 0.995518 11.00000 0.06360 0.06342 =
0.06407 0.01206 0.00409 0.00019
AFIX 43
H34 2 0.619200 0.012343 1.026363 11.00000 -1.20000
AFIX 65
C33 1 0.788557 0.003586 0.963167 11.00000 0.06052 0.05284 =
0.06459 0.00932 0.00641 -0.00396
AFIX 0
O40 6 1.127544 -0.085461 0.890882 11.00000 0.04711 0.07790 =
0.08276 0.01599 0.02460 0.01644
C15 1 1.307119 0.339537 0.708119 11.00000 0.06213 0.06224 =
0.11826 0.02046 0.01914 0.03755
C38 1 0.975224 0.005204 0.881823 11.00000 0.04354 0.05261 =
0.06323 -0.00766 0.00069 0.00129
O42 6 0.250657 0.291418 0.921121 11.00000 0.04775 0.06476 =
0.07179 -0.00527 0.00448 0.02166
AFIX 147
H42 2 0.156468 0.302044 0.943037 11.00000 -1.50000
AFIX 0
C14 1 1.241097 0.396907 0.756499 11.00000 0.07175 0.05946 =
0.11614 0.01108 0.01825 0.03317
AFIX 23
H14A 2 1.151605 0.326933 0.773690 11.00000 -1.20000
H14B 2 1.386475 0.415660 0.774296 11.00000 -1.20000
AFIX 0
O12 6 0.319128 1.000352 0.777420 11.00000 0.10562 0.06215 =
0.05842 0.02047 0.01539 0.05875
O41 6 0.958410 -0.098723 0.979153 11.00000 0.08745 0.05484 =
0.08657 0.02391 0.01346 0.00140
AFIX 147
H41 2 1.043887 -0.121798 0.956939 11.00000 -1.50000
AFIX 0
F13 4 0.511142 0.687962 0.904780 11.00000 0.13442 0.04474 =
0.05932 0.02529 0.02277 0.04116
O1 6 1.104010 0.519633 0.754011 11.00000 0.07126 0.05725 =
0.10301 0.00685 0.01843 0.03006
O39 6 0.968249 0.070756 0.839980 11.00000 0.04574 0.08392 =
0.06891 0.00476 0.00012 0.00094
AFIX 83
H39 2 1.072100 0.039139 0.822607 11.00000 -1.50000
AFIX 0
C17 1 1.138464 0.243388 0.628974 11.00000 0.07494 0.07188 =
0.12416 0.01796 0.01917 0.04083
AFIX 23
H17A 2 1.232176 0.158593 0.628400 11.00000 -1.20000
H17B 2 0.988301 0.225125 0.612765 11.00000 -1.20000
AFIX 0
O21 6 0.972465 0.185052 0.711047 11.00000 0.06816 0.09159 =
0.13581 0.03095 0.01270 0.01629
AFIX 83
H21 2 0.828359 0.200591 0.711408 11.00000 -1.50000
AFIX 0
C20 1 1.438313 0.447479 0.677458 11.00000 0.07447 0.06684 =
0.12488 0.02573 0.01979 0.03439
AFIX 23
H20A 2 1.346328 0.532911 0.678027 11.00000 -1.20000
H20B 2 1.591213 0.466927 0.692442 11.00000 -1.20000
AFIX 0
O22 6 1.469244 0.223555 0.714850 11.00000 0.04922 0.05663 =
0.14463 0.01240 0.02712 0.03643
AFIX 147
H22 2 1.401436 0.161832 0.729667 11.00000 -1.50000
AFIX 0
C16 1 1.087343 0.283135 0.680970 11.00000 0.06249 0.06470 =
0.12192 0.01841 0.01869 0.03910
AFIX 13
H16 2 0.976517 0.361826 0.679004 11.00000 -1.20000
AFIX 66
C23 1 1.265147 0.344425 0.551134 11.00000 0.12268 0.12783 =
0.14300 0.01214 0.01949 0.04092
C28 1 1.434432 0.263645 0.527994 11.00000 0.14609 0.14858 =
0.15420 -0.00697 0.01841 0.04320
C27 1 1.440441 0.260705 0.478667 11.00000 0.16507 0.16161 =
0.16639 -0.01097 0.01744 0.04052
AFIX 43
H27 2 1.553704 0.206657 0.463185 11.00000 -1.20000
AFIX 65
C26 1 1.277166 0.338545 0.452481 11.00000 0.17379 0.16835 =
0.16788 -0.00690 0.01452 0.03960
C25 1 1.107880 0.419326 0.475620 11.00000 0.16090 0.15927 =
0.16527 0.00490 0.01544 0.03969
AFIX 43
H25 2 0.998639 0.471406 0.458099 11.00000 -1.20000
AFIX 65
C24 1 1.101869 0.422267 0.524946 11.00000 0.14367 0.14646 =
0.15277 0.01163 0.01821 0.04528
AFIX 0
CL31 3 1.268152 0.321997 0.390454 11.00000 0.23401 0.22053 =
0.19061 -0.00797 0.00857 0.05804
F29 4 0.928685 0.501262 0.548351 11.00000 0.17117 0.17956 =
0.16483 0.02244 0.02454 0.05069
F30 4 1.614888 0.175910 0.550726 11.00000 0.16358 0.14228 =
0.16771 -0.04910 0.00913 0.05220
C19 1 1.484726 0.409918 0.625408 11.00000 0.07841 0.07204 =
0.12708 0.02993 0.02462 0.04086
AFIX 23
H19A 2 1.534890 0.492210 0.608241 11.00000 -1.20000
H19B 2 1.612402 0.341921 0.623696 11.00000 -1.20000
AFIX 0
N18 5 1.268100 0.353069 0.603398 11.00000 0.08813 0.09035 =
0.12610 0.02257 0.02236 0.03460
HKLF 4
REM merge_2254_2260 in P21 #4
REM wR2 = 0.480288, GooF = S = 1.07494, Restrained GooF = 1.03439 for all data
REM R1 = 0.160193 for 2030 Fo > 4sig(Fo) and 0.245506 for all 4096 data
REM 348 parameters refined using 537 restraints
END
WGHT 0.2000 0.0000
REM Highest difference peak 0.149, deepest hole -0.146, 1-sigma level 0.037
Q1 1 0.5745 0.6195 0.9162 11.00000 0.05 0.15
Q2 1 0.8285 0.8702 0.7263 11.00000 0.05 0.13
Q3 1 0.4854 0.0779 1.0329 11.00000 0.05 0.12
Q4 1 0.8395 -0.0445 0.9782 11.00000 0.05 0.12
;
_shelx_res_checksum 58307
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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 C2 0.960(3) 0.5589(17) 0.7945(6) 0.070(5) Uani d 1 . .
C C11 0.804(4) 0.6700(17) 0.7886(5) 0.068(4) Uani d 1 . .
C C6 0.660(3) 0.7121(17) 0.8261(6) 0.063(4) Uani d 1 . .
C C5 0.673(3) 0.6431(19) 0.8694(6) 0.072(5) Uani d 1 . .
C C4 0.829(3) 0.5320(19) 0.8752(5) 0.075(5) Uani d 1 . .
H H4 0.837583 0.485853 0.904220 0.090 Uiso calc 1 . .
C C3 0.973(3) 0.4899(16) 0.8378(6) 0.073(5) Uani d 1 . .
H H3 1.077324 0.415597 0.841680 0.087 Uiso calc 1 . .
C C10 0.796(5) 0.753(2) 0.7416(8) 0.069(5) Uani d 1 . .
H H10A 0.957975 0.785032 0.735893 0.083 Uiso calc 1 . .
H H10B 0.759602 0.686397 0.716684 0.083 Uiso calc 1 . .
C C9 0.631(5) 0.878(3) 0.7338(10) 0.075(5) Uani d 1 . .
H H9A 0.528342 0.859999 0.706630 0.090 Uiso calc 1 . .
H H9B 0.726751 0.959210 0.726908 0.090 Uiso calc 1 . .
C C8 0.476(5) 0.906(3) 0.7778(9) 0.068(5) Uani d 1 . .
N N7 0.479(5) 0.824(2) 0.8206(10) 0.067(5) Uani d 1 . .
H H7 0.359249 0.842859 0.846624 0.080 Uiso calc 1 . .
C C32 0.785(2) 0.0552(14) 0.9171(6) 0.053(4) Uani d 1 . .
C C37 0.611(3) 0.1500(15) 0.9033(5) 0.054(4) Uani d 1 . .
H H37 0.608891 0.184541 0.872468 0.065 Uiso calc 1 . .
C C36 0.440(2) 0.1933(15) 0.9357(6) 0.057(5) Uani d 1 . .
C C35 0.443(2) 0.1417(17) 0.9818(6) 0.059(5) Uani d 1 . .
H H35 0.327933 0.170661 1.003412 0.071 Uiso calc 1 . .
C C34 0.617(3) 0.0469(18) 0.9955(5) 0.064(5) Uani d 1 . .
H H34 0.619200 0.012343 1.026363 0.076 Uiso calc 1 . .
C C33 0.789(2) 0.0036(15) 0.9632(6) 0.059(4) Uani d 1 . .
O O40 1.128(4) -0.085(2) 0.8909(11) 0.069(6) Uani d 1 . .
C C15 1.307(4) 0.340(2) 0.7081(11) 0.081(5) Uani d 1 . .
C C38 0.975(3) 0.005(2) 0.8818(8) 0.053(4) Uani d 1 . .
O O42 0.251(4) 0.291(2) 0.9211(10) 0.061(6) Uani d 1 . .
H H42 0.156468 0.302044 0.943037 0.092 Uiso calc 1 . .
C C14 1.241(6) 0.397(3) 0.7565(12) 0.082(5) Uani d 1 . .
H H14A 1.151605 0.326933 0.773690 0.099 Uiso calc 1 . .
H H14B 1.386475 0.415660 0.774296 0.099 Uiso calc 1 . .
O O12 0.319(5) 1.000(2) 0.7774(9) 0.075(7) Uani d 1 . .
O O41 0.958(4) -0.099(2) 0.9792(11) 0.076(7) Uani d 1 . .
H H41 1.043887 -0.121798 0.956939 0.114 Uiso calc 1 . .
F F13 0.511(6) 0.688(2) 0.9048(10) 0.079(7) Uani d 1 . .
O O1 1.104(4) 0.520(2) 0.7540(12) 0.077(5) Uani d 1 . .
O O39 0.968(4) 0.071(2) 0.8400(11) 0.066(5) Uani d 1 . .
H H39 1.072100 0.039139 0.822607 0.099 Uiso calc 1 . .
C C17 1.138(5) 0.243(2) 0.6290(10) 0.090(6) Uani d 1 . .
H H17A 1.232176 0.158593 0.628400 0.108 Uiso calc 1 . .
H H17B 0.988301 0.225125 0.612765 0.108 Uiso calc 1 . .
O O21 0.972(5) 0.185(3) 0.7110(12) 0.098(8) Uani d 1 . .
H H21 0.828359 0.200591 0.711408 0.148 Uiso calc 1 . .
C C20 1.438(5) 0.447(2) 0.6775(10) 0.089(6) Uani d 1 . .
H H20A 1.346328 0.532911 0.678027 0.106 Uiso calc 1 . .
H H20B 1.591213 0.466927 0.692442 0.106 Uiso calc 1 . .
O O22 1.469(3) 0.224(2) 0.7149(14) 0.083(7) Uani d 1 . .
H H22 1.401436 0.161832 0.729667 0.125 Uiso calc 1 . .
C C16 1.087(4) 0.283(2) 0.6810(9) 0.083(5) Uani d 1 . .
H H16 0.976517 0.361826 0.679004 0.100 Uiso calc 1 . .
C C23 1.265(6) 0.344(3) 0.5511(9) 0.131(7) Uani d 1 . .
C C28 1.434(5) 0.264(3) 0.5280(10) 0.150(8) Uani d 1 . .
C C27 1.440(5) 0.261(3) 0.4787(10) 0.164(9) Uani d 1 . .
H H27 1.553704 0.206657 0.463185 0.197 Uiso calc 1 . .
C C26 1.277(6) 0.339(4) 0.4525(9) 0.170(9) Uani d 1 . .
C C25 1.108(5) 0.419(3) 0.4756(10) 0.162(9) Uani d 1 . .
H H25 0.998639 0.471406 0.458099 0.194 Uiso calc 1 . .
C C24 1.102(5) 0.422(3) 0.5249(10) 0.148(8) Uani d 1 . .
Cl Cl31 1.268(6) 0.322(4) 0.3905(9) 0.215(12) Uani d 1 . .
F F29 0.929(10) 0.501(5) 0.548(2) 0.172(14) Uani d 1 . .
F F30 1.615(9) 0.176(5) 0.551(2) 0.158(13) Uani d 1 . .
C C19 1.485(4) 0.410(3) 0.6254(10) 0.092(6) Uani d 1 . .
H H19A 1.534890 0.492210 0.608241 0.111 Uiso calc 1 . .
H H19B 1.612402 0.341921 0.623696 0.111 Uiso calc 1 . .
N N18 1.268(5) 0.353(3) 0.6034(11) 0.101(5) 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
C2 0.078(9) 0.057(8) 0.076(10) 0.029(7) 0.010(9) 0.005(8)
C11 0.085(9) 0.056(8) 0.062(9) 0.030(7) 0.008(8) 0.011(7)
C6 0.087(9) 0.043(7) 0.059(9) 0.034(7) 0.009(8) 0.015(7)
C5 0.088(10) 0.063(9) 0.066(10) 0.037(8) 0.007(9) 0.024(8)
C4 0.081(11) 0.069(10) 0.074(11) 0.037(8) 0.002(10) 0.020(9)
C3 0.082(11) 0.059(9) 0.076(11) 0.032(9) 0.002(10) 0.008(8)
C10 0.089(10) 0.058(9) 0.060(10) 0.031(8) 0.009(10) 0.011(8)
C9 0.096(11) 0.067(9) 0.062(11) 0.040(9) 0.015(10) 0.018(9)
C8 0.090(10) 0.058(8) 0.055(10) 0.045(8) 0.011(9) 0.013(8)
N7 0.096(10) 0.045(8) 0.059(10) 0.040(8) 0.015(9) 0.009(7)
C32 0.051(7) 0.050(7) 0.057(9) 0.005(6) 0.002(7) -0.002(7)
C37 0.055(8) 0.052(8) 0.055(10) 0.010(7) 0.008(8) -0.004(8)
C36 0.049(8) 0.064(9) 0.059(10) 0.015(7) 0.004(8) -0.004(8)
C35 0.052(9) 0.063(9) 0.062(10) 0.001(7) 0.009(9) 0.003(9)
C34 0.064(9) 0.063(9) 0.064(10) 0.000(8) 0.004(9) 0.012(9)
C33 0.061(8) 0.053(8) 0.065(10) -0.004(7) 0.006(8) 0.009(8)
O40 0.047(10) 0.078(12) 0.083(17) 0.016(9) 0.025(12) 0.016(12)
C15 0.062(8) 0.062(8) 0.118(11) 0.038(7) 0.019(9) 0.020(8)
C38 0.044(8) 0.053(9) 0.063(10) 0.001(7) 0.001(8) -0.008(8)
O42 0.048(10) 0.065(11) 0.072(16) 0.022(8) 0.004(12) -0.005(11)
C14 0.072(10) 0.059(9) 0.116(12) 0.033(9) 0.018(10) 0.011(9)
O12 0.106(15) 0.062(11) 0.058(15) 0.059(11) 0.015(13) 0.020(11)
O41 0.087(14) 0.055(10) 0.087(17) 0.001(9) 0.013(14) 0.024(12)
F13 0.134(17) 0.045(9) 0.059(14) 0.041(11) 0.023(13) 0.025(10)
O1 0.071(9) 0.057(8) 0.103(12) 0.030(8) 0.018(10) 0.007(9)
O39 0.046(10) 0.084(12) 0.069(13) 0.001(10) 0.000(11) 0.005(11)
C17 0.075(10) 0.072(10) 0.124(13) 0.041(9) 0.019(11) 0.018(10)
O21 0.068(12) 0.092(14) 0.14(2) 0.016(10) 0.013(15) 0.031(14)
C20 0.074(10) 0.067(9) 0.125(13) 0.034(8) 0.020(11) 0.026(10)
O22 0.049(10) 0.057(10) 0.14(2) 0.036(9) 0.027(13) 0.012(12)
C16 0.062(9) 0.065(9) 0.122(12) 0.039(8) 0.019(10) 0.018(9)
C23 0.123(13) 0.128(12) 0.143(14) 0.041(12) 0.019(14) 0.012(13)
C28 0.146(15) 0.149(15) 0.154(16) 0.043(14) 0.018(16) -0.007(15)
C27 0.165(16) 0.162(16) 0.166(18) 0.041(15) 0.017(18) -0.011(17)
C26 0.174(16) 0.168(16) 0.168(17) 0.040(15) 0.015(18) -0.007(16)
C25 0.161(16) 0.159(16) 0.165(18) 0.040(15) 0.015(18) 0.005(17)
C24 0.144(15) 0.146(15) 0.153(17) 0.045(14) 0.018(16) 0.012(15)
Cl31 0.23(2) 0.22(2) 0.19(2) 0.06(2) 0.01(2) -0.01(2)
F29 0.17(3) 0.18(3) 0.16(3) 0.05(2) 0.02(3) 0.02(2)
F30 0.16(2) 0.14(2) 0.17(3) 0.05(2) 0.01(3) -0.05(2)
C19 0.078(11) 0.072(10) 0.127(13) 0.041(9) 0.025(12) 0.030(11)
N18 0.088(10) 0.090(10) 0.126(12) 0.035(9) 0.022(11) 0.023(10)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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'
Cl Cl 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 '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
C11 C2 C3 . . 120.0 ?
C11 C2 O1 . . 117(2) ?
C3 C2 O1 . . 123(2) ?
C2 C11 C10 . . 120.8(16) ?
C6 C11 C2 . . 120.0 ?
C6 C11 C10 . . 119.2(19) ?
C11 C6 N7 . . 122(2) ?
C5 C6 C11 . . 120.0 ?
C5 C6 N7 . . 117.9(18) ?
C6 C5 C4 . . 120.0 ?
C6 C5 F13 . . 116(2) ?
C4 C5 F13 . . 124(2) ?
C5 C4 H4 . . 120.0 ?
C3 C4 C5 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C2 C3 H3 . . 120.0 ?
C4 C3 C2 . . 120.0 ?
C4 C3 H3 . . 120.0 ?
C11 C10 H10A . . 106.6 ?
C11 C10 H10B . . 106.6 ?
H10A C10 H10B . . 106.6 ?
C9 C10 C11 . . 123(2) ?
C9 C10 H10A . . 106.6 ?
C9 C10 H10B . . 106.6 ?
C10 C9 H9A . . 109.3 ?
C10 C9 H9B . . 109.3 ?
C10 C9 C8 . . 111(3) ?
H9A C9 H9B . . 108.0 ?
C8 C9 H9A . . 109.3 ?
C8 C9 H9B . . 109.3 ?
N7 C8 C9 . . 125(2) ?
O12 C8 C9 . . 121(3) ?
O12 C8 N7 . . 114(3) ?
C6 N7 H7 . . 120.4 ?
C8 N7 C6 . . 119(3) ?
C8 N7 H7 . . 120.4 ?
C37 C32 C33 . . 120.0 ?
C37 C32 C38 . . 121(2) ?
C33 C32 C38 . . 119.1(19) ?
C32 C37 H37 . . 120.0 ?
C36 C37 C32 . . 120.0 ?
C36 C37 H37 . . 120.0 ?
C37 C36 C35 . . 120.0 ?
C37 C36 O42 . . 120(3) ?
C35 C36 O42 . . 119.6(18) ?
C36 C35 H35 . . 120.0 ?
C34 C35 C36 . . 120.0 ?
C34 C35 H35 . . 120.0 ?
C35 C34 H34 . . 120.0 ?
C35 C34 C33 . . 120.0 ?
C33 C34 H34 . . 120.0 ?
C32 C33 O41 . . 122.8(19) ?
C34 C33 C32 . . 120.0 ?
C34 C33 O41 . . 117(3) ?
C14 C15 C20 . . 112(3) ?
C14 C15 C16 . . 112(3) ?
C20 C15 C16 . . 110(3) ?
O22 C15 C14 . . 109(3) ?
O22 C15 C20 . . 107(4) ?
O22 C15 C16 . . 107(4) ?
O40 C38 C32 . . 124(3) ?
O40 C38 O39 . . 122(2) ?
O39 C38 C32 . . 114(2) ?
C36 O42 H42 . . 109.5 ?
C15 C14 H14A . . 108.9 ?
C15 C14 H14B . . 108.9 ?
H14A C14 H14B . . 107.7 ?
O1 C14 C15 . . 113(3) ?
O1 C14 H14A . . 108.9 ?
O1 C14 H14B . . 108.9 ?
C33 O41 H41 . . 109.5 ?
C14 O1 C2 . . 119(3) ?
C38 O39 H39 . . 109.5 ?
H17A C17 H17B . . 107.9 ?
C16 C17 H17A . . 109.1 ?
C16 C17 H17B . . 109.1 ?
N18 C17 H17A . . 109.1 ?
N18 C17 H17B . . 109.1 ?
N18 C17 C16 . . 112(2) ?
C16 O21 H21 . . 109.5 ?
C15 C20 H20A . . 107.9 ?
C15 C20 H20B . . 107.9 ?
H20A C20 H20B . . 107.2 ?
C19 C20 C15 . . 117(2) ?
C19 C20 H20A . . 107.9 ?
C19 C20 H20B . . 107.9 ?
C15 O22 H22 . . 109.5 ?
C15 C16 H16 . . 105.0 ?
C17 C16 C15 . . 114(3) ?
C17 C16 H16 . . 105.0 ?
O21 C16 C15 . . 107(3) ?
O21 C16 C17 . . 119(3) ?
O21 C16 H16 . . 105.0 ?
C28 C23 C24 . . 120.0 ?
C28 C23 N18 . . 120(2) ?
C24 C23 N18 . . 120(2) ?
C23 C28 C27 . . 120.0 ?
C23 C28 F30 . . 126(3) ?
C27 C28 F30 . . 114(3) ?
C28 C27 H27 . . 120.0 ?
C26 C27 C28 . . 120.0 ?
C26 C27 H27 . . 120.0 ?
C27 C26 Cl31 . . 119.7(11) ?
C25 C26 C27 . . 120.0 ?
C25 C26 Cl31 . . 120.1(13) ?
C26 C25 H25 . . 120.0 ?
C26 C25 C24 . . 120.0 ?
C24 C25 H25 . . 120.0 ?
C23 C24 F29 . . 120(4) ?
C25 C24 C23 . . 120.0 ?
C25 C24 F29 . . 120(3) ?
C20 C19 H19A . . 109.6 ?
C20 C19 H19B . . 109.6 ?
H19A C19 H19B . . 108.1 ?
N18 C19 C20 . . 110(3) ?
N18 C19 H19A . . 109.6 ?
N18 C19 H19B . . 109.6 ?
C17 N18 C23 . . 116(3) ?
C19 N18 C17 . . 118(3) ?
C19 N18 C23 . . 117(3) ?
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
C2 C11 . 1.3900 ?
C2 C3 . 1.3900 ?
C2 O1 . 1.45(4) ?
C11 C6 . 1.3900 ?
C11 C10 . 1.55(2) ?
C6 C5 . 1.3900 ?
C6 N7 . 1.49(6) ?
C5 C4 . 1.3900 ?
C5 F13 . 1.42(5) ?
C4 H4 . 0.9300 ?
C4 C3 . 1.3900 ?
C3 H3 . 0.9300 ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C10 C9 . 1.53(5) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C9 C8 . 1.54(4) ?
C8 N7 . 1.44(4) ?
C8 O12 . 1.26(5) ?
N7 H7 . 1.0100 ?
C32 C37 . 1.3900 ?
C32 C33 . 1.3900 ?
C32 C38 . 1.53(5) ?
C37 H37 . 0.9300 ?
C37 C36 . 1.3900 ?
C36 C35 . 1.3900 ?
C36 O42 . 1.47(6) ?
C35 H35 . 0.9300 ?
C35 C34 . 1.3900 ?
C34 H34 . 0.9300 ?
C34 C33 . 1.3900 ?
C33 O41 . 1.44(5) ?
O40 C38 . 1.24(5) ?
C15 C14 . 1.52(4) ?
C15 C20 . 1.54(4) ?
C15 O22 . 1.45(5) ?
C15 C16 . 1.54(6) ?
C38 O39 . 1.34(4) ?
O42 H42 . 0.8200 ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C14 O1 . 1.41(5) ?
O41 H41 . 0.8200 ?
O39 H39 . 0.8200 ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C17 C16 . 1.54(2) ?
C17 N18 . 1.47(4) ?
O21 H21 . 0.8200 ?
O21 C16 . 1.42(3) ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
C20 C19 . 1.53(2) ?
O22 H22 . 0.8200 ?
C16 H16 . 0.9800 ?
C23 C28 . 1.3900 ?
C23 C24 . 1.3900 ?
C23 N18 . 1.47(4) ?
C28 C27 . 1.3900 ?
C28 F30 . 1.46(7) ?
C27 H27 . 0.9300 ?
C27 C26 . 1.3900 ?
C26 C25 . 1.3900 ?
C26 Cl31 . 1.75(3) ?
C25 H25 . 0.9300 ?
C25 C24 . 1.3900 ?
C24 F29 . 1.40(7) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C19 N18 . 1.46(6) ?
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
C3 H3 O42 1_655 0.93 2.71 3.40(7) 131.2 yes
C9 H9B O22 1_465 0.97 2.94 3.49(11) 116.9 yes
N7 H7 O40 1_465 1.01 1.93 2.93(9) 168.7 yes
C34 H34 O42 2_647 0.93 2.69 3.48(7) 143.0 yes
O42 H42 O41 2_657 0.82 2.48 3.23(6) 152.2 yes
O39 H39 O12 1_645 0.82 1.92 2.73(10) 169.2 yes
O21 H21 O22 1_455 0.82 2.02 2.84(18) 175.3 yes
O22 H22 O12 1_645 0.82 2.11 2.90(7) 164.1 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
C2 C11 C6 C5 . . . . 0.0 ?
C2 C11 C6 N7 . . . . -176(2) ?
C2 C11 C10 C9 . . . . -179(2) ?
C11 C2 C3 C4 . . . . 0.0 ?
C11 C2 O1 C14 . . . . -172(2) ?
C11 C6 C5 C4 . . . . 0.0 ?
C11 C6 C5 F13 . . . . -177(2) ?
C11 C6 N7 C8 . . . . -10(3) ?
C11 C10 C9 C8 . . . . -1(4) ?
C6 C11 C10 C9 . . . . -2(4) ?
C6 C5 C4 C3 . . . . 0.0 ?
C5 C6 N7 C8 . . . . 174(2) ?
C5 C4 C3 C2 . . . . 0.0 ?
C3 C2 C11 C6 . . . . 0.0 ?
C3 C2 C11 C10 . . . . 177(2) ?
C3 C2 O1 C14 . . . . 8(3) ?
C10 C11 C6 C5 . . . . -177(2) ?
C10 C11 C6 N7 . . . . 7(2) ?
C10 C9 C8 N7 . . . . -2(4) ?
C10 C9 C8 O12 . . . . -176(3) ?
C9 C8 N7 C6 . . . . 7(5) ?
N7 C6 C5 C4 . . . . 176(2) ?
N7 C6 C5 F13 . . . . -1(2) ?
C32 C37 C36 C35 . . . . 0.0 ?
C32 C37 C36 O42 . . . . -178.6(16) ?
C37 C32 C33 C34 . . . . 0.0 ?
C37 C32 C33 O41 . . . . 177.5(17) ?
C37 C32 C38 O40 . . . . -175.6(19) ?
C37 C32 C38 O39 . . . . 6(2) ?
C37 C36 C35 C34 . . . . 0.0 ?
C36 C35 C34 C33 . . . . 0.0 ?
C35 C34 C33 C32 . . . . 0.0 ?
C35 C34 C33 O41 . . . . -177.7(17) ?
C33 C32 C37 C36 . . . . 0.0 ?
C33 C32 C38 O40 . . . . 4(3) ?
C33 C32 C38 O39 . . . . -174.3(16) ?
C15 C14 O1 C2 . . . . 159(2) ?
C15 C20 C19 N18 . . . . 47(3) ?
C38 C32 C37 C36 . . . . 179.5(14) ?
C38 C32 C33 C34 . . . . -179.5(14) ?
C38 C32 C33 O41 . . . . -2(2) ?
O42 C36 C35 C34 . . . . 178.6(16) ?
C14 C15 C20 C19 . . . . -172(2) ?
C14 C15 C16 C17 . . . . 172(2) ?
C14 C15 C16 O21 . . . . -54(3) ?
O12 C8 N7 C6 . . . . -178(2) ?
F13 C5 C4 C3 . . . . 176(2) ?
O1 C2 C11 C6 . . . . 179.7(19) ?
O1 C2 C11 C10 . . . . -3(2) ?
O1 C2 C3 C4 . . . . -180(2) ?
C20 C15 C14 O1 . . . . 56(4) ?
C20 C15 C16 C17 . . . . 46(3) ?
C20 C15 C16 O21 . . . . -180(2) ?
C20 C19 N18 C17 . . . . -48(3) ?
C20 C19 N18 C23 . . . . 165(2) ?
O22 C15 C14 O1 . . . . 174(2) ?
O22 C15 C20 C19 . . . . 69(3) ?
O22 C15 C16 C17 . . . . -70(3) ?
O22 C15 C16 O21 . . . . 65(3) ?
C16 C15 C14 O1 . . . . -69(4) ?
C16 C15 C20 C19 . . . . -46(3) ?
C16 C17 N18 C23 . . . . -163(3) ?
C16 C17 N18 C19 . . . . 51(4) ?
C23 C28 C27 C26 . . . . 0.0 ?
C28 C23 C24 C25 . . . . 0.0 ?
C28 C23 C24 F29 . . . . 178.7(11) ?
C28 C23 N18 C17 . . . . -86(5) ?
C28 C23 N18 C19 . . . . 61(5) ?
C28 C27 C26 C25 . . . . 0.0 ?
C28 C27 C26 Cl31 . . . . -174(3) ?
C27 C26 C25 C24 . . . . 0.0 ?
C26 C25 C24 C23 . . . . 0.0 ?
C26 C25 C24 F29 . . . . -178.7(11) ?
C24 C23 C28 C27 . . . . 0.0 ?
C24 C23 C28 F30 . . . . -179(3) ?
C24 C23 N18 C17 . . . . 97(5) ?
C24 C23 N18 C19 . . . . -116(4) ?
Cl31 C26 C25 C24 . . . . 174(3) ?
F30 C28 C27 C26 . . . . 179(3) ?
N18 C17 C16 C15 . . . . -49(3) ?
N18 C17 C16 O21 . . . . -177(2) ?
N18 C23 C28 C27 . . . . -177(3) ?
N18 C23 C28 F30 . . . . 4(3) ?
N18 C23 C24 C25 . . . . 177(3) ?
N18 C23 C24 F29 . . . . -5(3) ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.747(10)
2 0.253(10)