#------------------------------------------------------------------------------
#$Date: 2025-04-05 13:40:53 +0200 (Sat, 05 Apr 2025) $
#$Revision: 299190 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/34/2023405.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_2023405
loop_
_publ_author_name
'Mewis, Ryan E.'
'Hulme, Matthew C.'
'Marron, Jack'
'Langley, Stuart K.'
'Sutcliffe, Oliver B.'
'Benjamin, Sophie L.'
_publ_section_title
;
Synthesis and crystal structures of five fluorinated diphenidine
derivatives.
;
_journal_coeditor_code EE2011
_journal_issue 'Pt 3'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first 229
_journal_page_last 234
_journal_paper_doi 10.1107/S2056989025001288
_journal_volume 81
_journal_year 2025
_chemical_formula_iupac 'C19 H19 F5 N +, Cl -'
_chemical_formula_moiety 'C19 H19 Cl F5 N +, Cl -'
_chemical_formula_sum 'C19 H19 Cl F5 N'
_chemical_formula_weight 391.80
_chemical_name_systematic
;
1-[1-(2,3,4,5,6-Pentafluorophenyl)-2-phenylethyl]piperidin-1-ium chloride
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_Hall '-P 2ybc'
_space_group_name_H-M_alt 'P 1 21/c 1'
_atom_sites_solution_hydrogens mixed
_audit_creation_method SHELXL-2018/3
_cell_angle_alpha 90
_cell_angle_beta 90.165(5)
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 9.3155(5)
_cell_length_b 22.2529(13)
_cell_length_c 8.2699(3)
_cell_measurement_reflns_used 9843
_cell_measurement_temperature 123(2)
_cell_measurement_theta_max 26.54
_cell_measurement_theta_min 3.04
_cell_volume 1714.32(15)
_computing_cell_refinement 'CrysAlisPro (Agilent, 2014)'
_computing_data_collection 'CrysAlisPro (Agilent, 2014)'
_computing_data_reduction 'CrysAlisPro (Agilent, 2014)'
_computing_molecular_graphics
;
X-SEED (Barbour, 2020)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature 123(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type 'Oxford Diffraction Xcalibur'
_diffrn_measurement_method 'scans in phi and omega'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0491
_diffrn_reflns_av_unetI/netI 0.0786
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 26
_diffrn_reflns_limit_k_min -18
_diffrn_reflns_limit_l_max 9
_diffrn_reflns_limit_l_min -8
_diffrn_reflns_number 5523
_diffrn_reflns_theta_full 25.000
_diffrn_reflns_theta_max 25.000
_diffrn_reflns_theta_min 3.069
_diffrn_source 'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu 0.277
_exptl_absorpt_correction_T_max 0.986
_exptl_absorpt_correction_T_min 0.967
_exptl_absorpt_correction_type analytical
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.518
_exptl_crystal_description block
_exptl_crystal_F_000 808
_exptl_crystal_size_max 0.2
_exptl_crystal_size_mid 0.1
_exptl_crystal_size_min 0.05
_refine_diff_density_max 0.299
_refine_diff_density_min -0.249
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.013
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 239
_refine_ls_number_reflns 2896
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.013
_refine_ls_R_factor_all 0.0862
_refine_ls_R_factor_gt 0.0556
_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^)+(0.0452P)^2^+0.3121P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1082
_refine_ls_wR_factor_ref 0.1225
_reflns_number_gt 2117
_reflns_number_total 2896
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file ee2011.cif
_cod_data_source_block V
_cod_depositor_comments
'Adding full bibliography for 2023405--2023409.cif.'
_cod_original_sg_symbol_H-M 'P 21/c'
_cod_database_code 2023405
_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 0 2 1794.75 46.9642 4
0 0 2 1950.09 75.9492 3
0 0 3 16.1250 16.9978 3
0 0 3-18.8606 14.1533 1
0 0 3-11.3645 9.78460 4
0 0 4 2586.65 109.535 1
0 0 4 2770.40 130.713 3
0 0 4 2714.04 78.2161 4
0 0 5 40.8284 30.9052 3
0 0 5 1.45452 16.0267 1
0 0 5 3.97675 9.65837 4
0 0 6 104.288 30.8978 1
0 0 6 130.883 18.8145 4
0 0 6 204.700 55.0005 3
0 0 7 1.08793 14.1281 1
0 0 7-42.1538 30.7274 3
0 0 7-10.7630 7.68910 4
0 0 8 3198.87 212.178 3
0 0 8 4227.10 202.733 1
0 0 9 8.88291 31.2271 3
0 0 10 255.946 87.4480 3
0 1 2 3947.25 110.158 3
0 1 -2 3574.67 71.3346 4
0 -1 2 3880.72 99.9300 3
0 -1 2 3587.64 71.0158 4
0 1 -2 3592.81 93.2532 1
0 1 -3 10527.2 144.359 4
0 1 3 10592.0 218.287 3
0 -1 3 10409.7 209.248 3
0 1 3 10130.8 138.736 4
0 -1 3 10439.5 139.563 4
0 -1 3 9695.90 184.547 1
0 1 4 485.541 33.6071 4
0 1 4 476.489 56.0405 3
0 -1 4 518.730 34.6383 4
0 -1 4 466.050 53.7287 3
0 -1 4 459.244 45.4297 1
0 -1 5 10051.3 159.505 4
0 1 5 9876.46 237.332 1
0 1 5 9150.40 277.050 3
0 -1 5 9781.29 239.776 1
0 1 5 9265.71 159.076 4
0 -1 5 9478.63 274.811 3
0 -1 6 208.860 24.4851 4
0 -1 6 126.004 26.8472 1
0 1 6 207.017 24.7200 4
0 -1 6 170.878 45.4313 3
0 1 6 238.343 51.9590 3
0 1 6 162.094 32.6175 1
0 1 7 85.0539 39.6817 3
0 -1 7 125.118 28.8827 1
0 1 7 132.637 35.4381 1
0 -1 7 87.0946 36.5126 3
0 1 7 86.9536 13.5434 4
0 1 8 555.680 93.7890 1
0 1 8 267.344 68.6633 3
0 -1 8 357.956 72.3885 3
0 1 9 88.0488 45.2818 3
0 -1 9 103.250 44.4344 3
0 1 9 96.6710 43.2044 1
0 -1 10 149.369 63.2158 3
0 1 10 107.672 52.6092 3
0 -1 11 135.057 39.9787 3
0 2 -1 3873.54 73.6552 4
0 2 2 25839.2 293.056 3
0 -2 2 23920.0 207.072 4
0 2 -2 22808.4 244.054 1
0 2 -2 23656.4 208.221 4
0 -2 2 24360.9 240.812 3
0 -2 3 1456.83 56.9120 4
0 2 -3 1383.35 72.3403 1
0 2 3 1512.40 86.9462 3
0 -2 3 1476.66 74.9846 1
0 2 -3 1457.27 58.1038 4
0 -2 3 1535.56 79.4081 3
0 2 4 4312.61 167.416 3
0 2 -4 4570.30 115.860 4
0 -2 4 4708.16 109.911 4
0 2 4 4435.78 106.865 4
0 -2 4 4328.87 146.422 1
0 -2 4 4444.37 160.078 3
0 -2 5 142.052 36.8453 3
0 2 5 148.828 36.5877 3
0 2 5 159.165 22.2742 4
0 -2 5 167.974 32.1090 1
0 -2 5 181.340 24.4521 4
0 -2 6 1012.96 56.9286 4
0 2 6 1019.91 55.8095 4
0 2 6 1102.07 106.466 3
0 2 6 1081.71 90.1947 1
0 -2 6 913.348 94.4566 3
0 -2 6 1040.79 89.1428 1
0 2 7 36.1708 25.9036 1
0 2 7 6.62740 7.17482 4
0 -2 7-14.7202 21.6873 3
0 2 7-25.5364 22.1883 3
0 -2 8 832.097 107.453 3
0 2 8 781.824 111.661 3
0 2 8 1076.70 98.9363 1
0 -2 9 252.198 61.5980 3
0 2 9 149.552 43.2077 1
0 2 9 174.188 63.7973 3
0 2 10 201.754 70.6238 3
0 -2 10 292.411 79.5330 3
0 -2 11 25.9264 45.4476 3
0 3 -1 420.235 29.9728 4
0 3 1 455.766 31.6684 3
0 3 -2 16936.8 231.143 1
0 3 -2 17277.9 201.063 4
0 -3 2 16762.1 199.657 4
0 3 2 18004.1 253.855 3
0 -3 2 17053.6 193.832 3
0 3 -3 9991.86 168.846 4
0 3 -3 10004.3 196.103 1
0 -3 3 10083.0 164.543 4
0 -3 3 10296.0 200.574 3
0 3 3 10446.2 227.990 3
0 3 -4 64.0802 16.1653 4
0 -3 4 78.7050 28.5006 3
0 3 4 60.4863 24.9467 3
0 3 -4 85.9677 26.3642 1
0 -3 4 67.9596 17.9645 4
0 3 5 904.366 54.6487 4
0 3 5 885.465 87.1393 3
0 3 -5 968.899 63.1832 4
0 -3 5 912.727 83.9916 3
0 -3 5 908.749 57.7702 4
0 -3 6 161.335 45.8759 3
0 3 6 99.8710 37.7243 3
0 3 6 126.317 21.5949 4
0 3 7 305.679 29.6954 4
0 3 7 455.578 62.5117 1
0 -3 7 368.065 63.0211 3
0 3 7 358.982 68.0884 3
0 3 8 1007.80 96.9615 1
0 3 8 844.011 111.012 3
0 -3 8 738.708 101.030 3
0 3 9 113.125 43.5028 1
0 -3 9 92.4928 46.1234 3
0 3 9 86.0827 44.8161 3
0 -3 10 37.9055 37.9767 3
0 3 10 108.871 53.5591 3
0 -3 11 228.983 74.4200 3
0 4 0 2942.02 53.2293 3
0 4 -1 473.454 25.0477 2
0 4 1 602.999 37.9797 3
0 4 -1 569.185 39.3640 4
0 4 -2 4441.58 112.574 4
0 -4 2 4461.33 97.0053 3
0 4 2 4706.70 134.196 3
0 -4 2 4314.84 105.418 2
0 -4 3 368.948 38.2672 3
0 4 -3 404.850 37.8228 4
0 4 3 447.440 50.3843 3
0 -4 3 366.376 37.0991 4
0 4 -3 367.082 42.4741 1
0 -4 4 204.430 34.6997 3
0 4 -4 216.845 32.9670 4
0 4 4 143.957 35.2017 3
0 -4 4 139.312 24.6738 4
0 4 -4 176.201 32.8997 1
0 -4 5 1202.16 93.8074 3
0 4 -5 1213.64 73.4361 4
0 4 5 1157.73 102.024 3
0 4 -6 422.948 47.1840 4
0 4 6 401.407 68.3411 3
0 4 6 440.528 42.4900 4
0 -4 6 350.780 60.4491 3
0 -4 7 35.2380 29.3501 3
0 4 7 57.4766 34.3772 3
0 4 7 35.7345 21.8754 1
0 4 8 78.7266 39.4206 1
0 -4 8 27.2820 35.3760 3
0 4 8 78.7324 45.1404 3
0 -4 9 139.609 59.8768 3
0 4 9 74.7820 32.7426 1
0 4 9 116.176 50.1040 3
0 -4 10 189.716 70.6990 3
0 4 10 51.2732 40.7378 3
0 -4 11 173.306 80.5800 2
0 5 0 4.74683 7.00921 3
0 5 -1 1473.00 70.2589 4
0 5 1 1700.61 66.5502 3
0 5 -2 2195.94 87.2208 4
0 -5 2 2238.32 75.4054 2
0 -5 2 2128.50 60.0840 3
0 5 2 2412.80 99.5445 3
0 5 -3 2005.42 99.6451 1
0 5 3 1980.38 104.586 3
0 5 -3 2028.16 88.8935 4
0 -5 3 1846.56 79.6503 3
0 5 -4 3379.04 119.989 4
0 -5 4 3211.39 129.938 3
0 5 4 3398.46 156.429 3
0 5 -4 3557.71 140.739 1
0 5 5 1036.98 100.504 3
0 -5 5 992.935 83.2247 3
0 5 -5 1154.49 91.2060 1
0 5 -5 1006.58 67.7237 4
0 5 6 40.5708 19.7983 4
0 5 6-29.4024 26.1922 3
0 -5 6-28.4174 27.3700 3
0 5 -6 49.1808 25.7004 4
0 -5 7 163.792 47.5329 3
0 5 7 215.774 57.2444 3
0 5 8 29.4923 28.8233 1
0 -5 8-3.10044 34.5929 3
0 5 8 34.4908 33.3351 3
0 -5 9 820.647 110.805 3
0 5 9 1049.34 104.645 1
0 5 9 815.436 117.248 3
0 -5 10 722.459 113.496 3
0 -5 10 475.500 97.4532 2
0 5 10 779.785 129.386 3
0 -5 11 129.709 68.1924 2
0 6 0 3048.35 66.4274 3
0 6 -1 115.240 25.5158 4
0 6 1 125.487 21.0541 3
0 6 2 2102.94 95.2122 3
0 6 -2 1936.32 88.4373 4
0 -6 2 1642.67 50.5594 3
0 -6 2 1994.46 71.1312 2
0 -6 3 474.307 38.5624 3
0 -6 3 519.851 46.7672 2
0 6 3 534.092 54.9849 3
0 6 -3 528.397 50.9606 4
0 6 -4 133.734 27.9244 4
0 6 4 270.954 49.8776 3
0 6 -4 256.190 41.4225 1
0 -6 4 192.892 30.6894 3
0 6 -5 79.0837 28.1829 4
0 6 -5 114.910 36.7719 1
0 -6 5 56.3286 22.0623 3
0 6 5 96.8881 33.0427 3
0 6 6 217.378 61.1128 3
0 -6 6 171.298 40.8759 3
0 6 -6 184.552 37.5145 4
0 6 -7 213.627 42.0636 4
0 -6 7 101.761 31.1445 3
0 6 7 104.711 43.2312 3
0 6 8 11.7515 37.0804 3
0 6 8 203.996 49.2567 1
0 -6 8 144.376 48.2867 3
0 -6 9-21.5044 36.9980 3
0 -6 9 32.2695 48.5599 2
0 6 9 48.0629 55.5768 3
0 6 10 225.672 83.9891 3
0 -6 10 134.212 56.8373 2
0 -6 10 190.844 61.0835 3
0 7 0-5.45750 9.13713 3
0 7 1 1643.73 72.6745 3
0 7 -2 133.801 28.3870 4
0 7 2 147.600 27.9927 3
0 -7 3 333.060 38.9178 2
0 7 -3 334.619 43.9800 4
0 -7 3 386.368 32.8234 3
0 7 3 398.708 51.8370 3
0 -7 4 119.437 22.2625 3
0 -7 4 87.1957 28.8376 2
0 7 -4 162.181 34.8590 1
0 7 4 80.1858 27.5141 3
0 7 -4 79.9194 23.4920 4
0 7 5 1214.95 110.580 3
0 7 -5 1130.09 84.4023 4
0 -7 5 1071.11 79.1783 3
0 7 -5 1314.53 101.196 1
0 -7 5 1114.05 91.8130 2
0 -7 6 964.056 89.0430 3
0 7 -6 1087.68 82.2183 4
0 7 6 1129.91 119.456 3
0 -7 6 1055.73 99.7726 2
0 -7 7 118.492 48.1866 2
0 7 7 63.1466 27.2365 3
0 -7 7 108.740 35.1981 3
0 7 -7 128.292 31.6661 4
0 7 8 124.495 45.2421 3
0 -7 8 171.585 44.3478 3
0 -7 8 127.813 41.7692 2
0 -7 9 207.283 58.3439 2
0 -7 9 263.956 72.4150 3
0 7 9 277.534 68.5473 3
0 7 10 71.5924 40.2098 3
0 -7 10 54.4721 40.2167 2
0 8 0 8960.25 134.709 3
0 8 1 256.113 31.3382 3
0 8 2 197.453 32.3583 3
0 8 -2 195.686 35.2173 4
0 8 3 1423.19 96.2272 3
0 8 -3 1406.36 89.4181 4
0 -8 3 1435.05 75.8427 2
0 8 4 70.2185 33.8343 3
0 -8 4 61.0317 21.0942 3
0 8 -4 12.5851 16.8039 4
0 -8 4 69.2352 21.3702 2
0 8 -4 39.8233 24.3534 1
0 -8 5 54.3136 21.3591 3
0 -8 5 53.0070 24.3620 2
0 8 5-10.6239 27.5010 3
0 8 -5 42.6248 23.4368 4
0 -8 6 1397.70 107.363 3
0 -8 6 1342.31 113.428 2
0 8 6 1523.67 137.211 3
0 8 -6 1447.27 99.8114 4
0 -8 7 158.254 46.0910 3
0 -8 7 298.625 58.3570 2
0 8 7 237.344 61.0179 3
0 8 -7 228.841 46.2124 4
0 8 8 612.351 102.795 3
0 -8 8 700.034 95.3042 3
0 -8 8 643.315 96.7176 2
0 8 9 82.4724 38.2820 3
0 -8 9 49.7795 45.8662 2
0 9 0 25.6855 12.0847 3
0 9 1 7496.75 166.216 3
0 9 -2-9.24299 16.1937 4
0 9 -2 20.6086 11.5639 2
0 9 2 20.3082 19.4128 3
0 9 -3 3972.69 154.016 4
0 9 3 3847.53 161.435 3
0 9 4 499.577 68.2075 3
0 9 -4 472.100 56.4166 4
0 -9 4 469.824 50.3655 2
0 9 -5 77.0306 28.9032 4
0 9 5 111.023 37.9057 3
0 -9 5 150.666 33.8730 3
0 -9 5 178.983 39.6065 2
0 9 -6 274.455 54.3017 4
0 -9 6 141.166 38.5018 2
0 9 6 153.881 45.1565 3
0 -9 6 153.913 38.2486 3
0 9 -7 80.3732 31.8097 4
0 9 7 103.824 40.8870 3
0 -9 7 44.3481 26.4228 3
0 -9 7 46.7844 28.6829 2
0 -9 8 125.188 49.1526 2
0 9 8 54.5114 41.6484 3
0 -9 9 59.5900 47.8443 2
0 9 9 74.7948 50.4012 3
0 10 0 9.29512 7.94220 3
0 10 -1 592.489 64.6023 4
0 10 1 663.952 52.7100 3
0 10 -2 700.834 43.3056 2
0 10 -2 745.723 70.6900 4
0 10 2 665.498 61.4108 3
0 10 -3 2561.86 132.060 4
0 10 3 2741.64 138.099 3
0 10 -4 195.712 45.4991 4
0 10 4 62.4340 31.8054 3
0 10 5 2248.59 156.851 3
0 -10 5 2020.86 117.678 2
0 10 -5 2208.71 129.973 4
0 10 6 1258.17 128.613 3
0 -10 6 1264.66 104.845 2
0 10 -6 1411.71 109.995 4
0 10 -7-6.76947 21.2659 4
0 10 7-1.60299 25.2313 3
0 -10 7 33.5135 31.0584 2
0 -10 8 630.497 90.1862 2
0 10 8 671.382 106.158 3
0 10 9 259.237 70.6280 3
0 11 0-3.96198 17.7534 3
0 11 1 40.1759 16.2572 3
0 11 -1 59.8858 20.9394 4
0 11 -2 76.5087 17.3284 2
0 11 2 126.610 30.0475 3
0 11 -2 178.492 38.0247 4
0 11 3 1675.73 112.946 3
0 11 -3 1650.21 109.752 4
0 11 4 786.569 85.8396 3
0 11 -4 787.007 80.7025 4
0 11 5 776.866 94.9024 3
0 11 -5 772.971 80.4117 4
0 11 6 7.62283 21.7331 3
0 -11 6 27.3229 27.6858 2
0 11 -6 3.76069 23.7694 4
0 11 -7 128.620 42.0985 4
0 11 7 65.9338 47.1727 3
0 -11 7 10.7722 28.5769 2
0 11 8 141.174 55.4794 3
0 -11 8 154.349 51.8136 2
0 11 9 76.9597 59.3174 3
0 12 0 739.886 46.2066 3
0 12 -1 49.9268 25.9751 4
0 12 1 62.4665 21.3205 3
0 12 -2 928.207 52.3540 2
0 12 2 1178.19 85.8562 3
0 12 -2 1161.04 96.4901 4
0 12 -3 261.499 49.0469 4
0 12 3 261.987 50.5415 3
0 12 4-1.69375 18.7348 3
0 12 -4 46.6057 28.4843 4
0 12 -5 328.983 64.6438 4
0 12 5 391.060 68.3068 3
0 12 6 1076.11 122.644 3
0 12 -6 1248.53 108.779 4
0 12 -7 2078.57 145.833 4
0 12 7 1749.01 165.261 3
0 -12 7 1807.49 136.790 2
0 12 8 438.446 87.7796 3
0 12 9 316.083 82.1443 3
0 13 0 21.3817 12.4018 3
0 13 1 229.806 35.8906 3
0 13 -1 230.361 46.9601 4
0 13 2 1450.47 99.1000 3
0 13 -2 1261.46 63.1348 2
0 13 -2 1490.12 113.885 4
0 13 3 1486.42 111.223 3
0 13 -3 1260.29 105.355 4
0 13 4 36.9860 29.5404 3
0 13 -4 23.7880 24.0523 4
0 13 5 247.297 56.8003 3
0 13 -5 282.792 54.6192 4
0 13 6 691.224 101.582 3
0 13 -6 757.490 89.9590 4
0 13 7 28.2504 25.4250 3
0 13 -7 73.6404 48.6251 4
0 13 8-9.83043 37.1136 3
0 13 9 15.4724 29.2955 3
0 14 0 3279.39 102.449 3
0 14 -1 994.694 97.7657 4
0 14 1 999.081 72.1798 3
0 14 -2 437.528 68.8027 4
0 14 2 501.919 61.0324 3
0 14 -2 388.206 36.8980 2
0 14 -3 46.5544 27.0809 4
0 14 3 64.4152 29.4976 3
0 14 4 184.109 46.2603 3
0 14 -4 193.226 48.0379 4
0 14 -5 418.517 67.1541 4
0 14 5 300.283 60.2883 3
0 14 -6 80.6563 39.4003 4
0 14 6 66.8204 35.2672 3
0 14 -7 103.621 45.4045 4
0 14 7 23.3529 36.7260 3
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10 3 0 20.7588 32.7523 1
10 3 1 746.256 108.782 1
10 3 2 175.184 56.8531 1
10 -3 2 107.697 57.2763 1
10 3 3 145.406 59.0895 1
10 -3 3-45.4075 60.6705 1
10 3 4 30.9402 50.5939 1
10 -3 4 0.52768 38.0962 1
10 3 5 72.7482 50.8060 1
10 -3 5-25.0963 57.0904 1
10 4 -1 51.1371 35.8789 1
10 4 0 1034.16 128.015 1
10 4 1 79.6427 42.7349 1
10 4 2 50.4496 48.2276 1
10 4 3 47.1294 52.4510 1
10 4 4 74.7077 63.0125 1
10 4 5 45.9388 61.0529 1
10 5 -1 8.67168 25.7184 1
10 5 0 45.8806 31.7438 1
10 5 1 103.767 57.6178 1
10 5 2 524.272 97.0560 1
10 5 3 296.951 85.5096 1
10 5 4-2.84445 42.2421 1
10 5 5 323.813 93.6604 1
10 6 -1 140.620 48.8242 1
10 6 0 754.897 110.533 1
10 6 1 694.389 109.074 1
10 6 2 274.093 75.6309 1
10 6 3 37.1658 71.1292 1
10 6 4 149.682 72.7029 1
10 6 5 103.162 63.9536 1
10 7 -1 8.60503 37.2674 1
10 7 0 123.407 50.4936 1
10 7 1 54.2435 53.7487 1
10 7 2 76.0582 50.7256 1
10 7 3 1738.63 184.112 1
10 7 4 115.299 68.7806 1
10 8 -1 181.072 55.4084 1
10 8 0 304.385 78.3375 1
-10 8 0 587.498 104.234 4
10 8 1-18.8459 30.9704 1
-10 8 -1 12.6630 30.9133 4
10 8 2-9.40214 34.7378 1
-10 8 -2 67.6498 61.7536 4
10 8 3 104.873 59.9089 1
10 8 4 50.2861 61.0406 1
-10 9 2 106.145 48.4607 4
-10 9 1-52.5495 44.7096 4
-10 9 0 95.0453 51.6164 4
-10 9 -1 463.956 99.6025 4
-10 9 -2 635.220 114.572 4
-10 9 -3 745.851 130.430 4
10 9 4 295.936 98.6197 1
-10 10 2 550.734 98.2092 4
-10 10 1 23.0263 26.0751 4
-10 10 0 290.649 87.8585 4
-10 10 -1 53.0559 48.8931 4
-10 10 -2 119.219 54.8349 4
-10 10 -3 11.1614 33.0227 4
-10 11 3 17.1390 36.8027 4
-10 11 2 282.040 69.3581 4
-10 11 1 38.6272 28.7003 4
-10 11 0 52.4909 44.3911 4
-10 11 -1 827.198 130.257 4
-10 11 -2 138.297 60.9092 4
-10 11 -3 473.980 105.353 4
-10 12 3 101.541 46.4984 4
-10 12 2 70.6715 47.8970 4
-10 12 1 180.248 63.3873 4
-10 12 0 175.233 73.0727 4
-10 12 -1 233.935 79.3329 4
-10 12 -2 88.0041 60.6353 4
-10 13 3 73.8092 36.8536 4
-10 13 2 7.32323 41.9545 4
-10 13 1 311.691 84.4355 4
-10 13 0 56.9872 52.2834 4
-10 13 -1 298.338 84.9856 4
-10 13 -2 125.136 66.2167 4
-10 14 3 43.2438 28.5148 4
-10 14 2 132.429 46.7229 4
-10 14 1 96.2721 56.0961 4
-10 14 0 346.105 91.8262 4
-10 14 -1-9.91999 55.7267 4
-10 15 3 129.929 58.4632 4
-10 15 2 21.1029 31.7053 4
-10 15 1 241.384 80.4839 4
-10 15 0 250.689 84.8138 4
-10 16 3 138.868 63.2511 4
-10 16 2 195.548 77.4714 4
-10 16 1 301.573 89.3832 4
-10 17 3 101.945 59.1601 4
11 0 0 68.1912 30.3821 1
11 0 1-48.2261 61.9974 1
11 0 2 251.751 68.9268 1
11 0 3 144.052 60.5554 1
11 0 4 1946.04 214.450 1
11 1 0-9.94475 25.1756 1
11 1 1 124.099 44.8714 1
11 -1 1 127.982 35.9243 1
11 1 2 30.9105 41.1003 1
11 -1 2 57.1235 52.4015 1
11 1 3 288.275 85.1930 1
11 -1 3 244.929 67.1919 1
11 1 4 94.8017 103.605 1
11 -1 4 142.750 59.3112 1
11 2 0 239.528 64.0068 1
11 2 1 455.367 92.9953 1
11 -2 2 348.199 86.8090 1
11 2 2 495.228 98.3160 1
11 -2 3 13.5751 34.8143 1
11 2 3 154.803 66.6360 1
11 -2 4 219.033 68.4246 1
11 2 4 327.035 89.7518 1
11 3 0 88.7258 47.6472 1
11 3 1 413.805 96.9342 1
11 3 2 4.75029 39.0591 1
11 3 3 9.40932 34.1709 1
11 3 4 363.916 93.0132 1
11 4 0 63.8405 41.0393 1
11 4 1 76.5579 44.6671 1
11 4 2 127.545 55.5366 1
11 4 3 62.9508 52.4369 1
11 5 0 144.138 55.5209 1
11 5 1 68.0975 42.2540 1
11 5 2 98.0236 56.4035 1
11 5 3 31.8518 41.6885 1
11 6 0 13.8921 40.0536 1
11 6 1 231.522 72.8272 1
11 6 2 313.149 79.0406 1
11 6 3 33.4638 31.8559 1
11 7 0 45.3464 40.8258 1
11 7 1 51.5384 42.0591 1
11 7 2 92.5224 60.9937 1
11 7 3 110.614 60.0370 1
11 8 0 36.7249 37.8543 1
11 8 1 122.737 57.7819 1
11 8 2 146.467 76.5898 1
11 8 3 33.8985 53.5974 1
11 9 0 51.1942 42.8515 1
11 9 1 78.7460 48.2436 1
11 9 2 196.096 76.2419 1
11 9 3 257.738 78.1022 1
11 10 0 317.248 91.9839 1
11 10 1 131.704 61.3561 1
11 10 2 81.2689 62.5657 1
-11 11 1-0.20530 37.5688 4
-11 11 0 1078.87 145.978 4
-11 12 2 364.275 92.1022 4
-11 12 1 17.7681 42.3283 4
-11 13 3 101.862 61.7214 4
-11 13 2 510.900 97.8347 4
12 0 1 80.4401 63.7026 1
12 0 2 294.951 93.2668 1
12 1 1 22.2453 30.0988 1
12 1 2-27.2034 47.5873 1
12 2 1-1.50406 49.5235 1
12 2 2 59.4903 44.0906 1
12 3 1 169.336 71.1634 1
12 3 2 35.4967 39.6858 1
12 4 1 2.50718 29.2457 1
12 4 2 94.0589 46.8800 1
12 5 1 176.008 71.0169 1
12 5 2 178.332 70.0325 1
12 6 1-21.3763 30.8969 1
12 6 2 86.0804 46.3573 1
12 7 1 306.765 81.7958 1
12 7 2 109.191 55.1894 1
0 0 0 0.00 0.00 0
TITL OS2 recollect3 in P2(1)/c
REM P2(1)/c (#14 in standard setting)
CELL 0.71073 9.315504 22.252866 8.269873 90.0000 90.1650 90.0000
ZERR 4.00 0.000473 0.001273 0.000349 0.0000 0.0048 0.0000
LATT 1
SYMM -x, y+1/2,-z+1/2
SFAC C H N F
UNIT 76.00 72.00 4.00 20.00
TREF
HKLF 4
END
;
_shelx_res_file
;
REM reset to P21/c #14
REM
REM
REM
REM OS2 recollect3 in P21/c #14
REM R1 = 0.0658 for 2424 Fo > 4sig(Fo) and 0.1079 for all 3546 data
REM 235 parameters refined using 0 restraints
REM Highest difference peak 0.363, deepest hole -0.251, 1-sigma level 0.068
REM OS2 recollect3 in P21/c #14
REM wR2 = 0.1183, GooF = S = 1.063, Restrained GooF = 1.063 for all data
REM R1 = 0.0561 for 2117 Fo > 4sig(Fo) and 0.0867 for all 2896 data
REM 235 parameters refined using 0 restraints
REM Highest difference peak 0.289, deepest hole -0.313, 1-sigma level 0.059
TITL OS2 recollect3 in P21/c #14
C:\Users\stula\Desktop\OS2R-V~1\OS2r.res
created by SHELXL-2018/3 at 10:30:23 on 29-Jan-2025
CELL 0.71073 9.3155 22.2529 8.2699 90.000 90.165 90.000
ZERR 4.0000 0.0005 0.0013 0.0003 0.000 0.005 0.000
LATT 1
SYMM -X, 0.5+Y, 0.5-Z
SFAC C H CL F N
UNIT 76 76 4 20 4
MERG 2
OMIT -2 50
SHEL 7.00 0.77
FMAP 2
GRID
PLAN 5
TEMP -100
BOND $H
HTAB N1 CL1
L.S. 20
ACTA
WGHT 0.045200 0.312100
FVAR 1.25937
CL1 3 0.242691 0.510189 0.689216 11.00000 0.02380 0.04209 =
0.02857 0.00240 0.00071 0.00158
F1 4 0.073308 0.426672 0.055497 11.00000 0.02339 0.04572 =
0.02894 0.00253 -0.00597 -0.00085
F5 4 0.312047 0.369120 0.535965 11.00000 0.02217 0.03869 =
0.03128 0.00625 -0.00490 -0.00096
F4 4 0.119037 0.282121 0.580136 11.00000 0.04040 0.03617 =
0.04463 0.01089 0.00806 -0.00405
F2 4 -0.116625 0.339638 0.100983 11.00000 0.02900 0.06679 =
0.04643 -0.01259 -0.00837 -0.01718
F3 4 -0.097652 0.266132 0.362500 11.00000 0.04180 0.04615 =
0.05956 -0.00717 0.00882 -0.02804
C14 1 0.198852 0.402786 0.296908 11.00000 0.01281 0.02565 =
0.02706 -0.00455 0.00542 0.00309
C18 1 0.108124 0.318068 0.449667 11.00000 0.02953 0.02775 =
0.02707 0.00214 0.00613 0.00128
C6 1 0.316688 0.449323 0.272314 11.00000 0.01230 0.02485 =
0.02734 -0.00051 0.00132 0.00051
AFIX 13
H6 2 0.395538 0.438117 0.348882 11.00000 -1.20000
AFIX 0
C5 1 0.133397 0.534693 0.244512 11.00000 0.01428 0.03408 =
0.02854 -0.00151 -0.00375 0.00288
AFIX 23
H5A 2 0.055024 0.505280 0.260780 11.00000 -1.20000
H5B 2 0.148162 0.539641 0.126760 11.00000 -1.20000
AFIX 0
C4 1 0.092152 0.594156 0.318230 11.00000 0.01732 0.03871 =
0.03621 -0.00185 -0.00463 0.00731
AFIX 23
H4A 2 0.070518 0.588238 0.434277 11.00000 -1.20000
H4B 2 0.003969 0.609188 0.264765 11.00000 -1.20000
AFIX 0
C8 1 0.420488 0.383953 0.052866 11.00000 0.01877 0.02822 =
0.02684 0.00335 0.00786 -0.00007
C1 1 0.388255 0.556974 0.300186 11.00000 0.01403 0.03323 =
0.03291 0.00302 0.00199 -0.00443
AFIX 23
H1A 2 0.477032 0.541589 0.351631 11.00000 -1.20000
H1B 2 0.407412 0.562601 0.183476 11.00000 -1.20000
AFIX 0
C19 1 0.206615 0.363641 0.427295 11.00000 0.01708 0.02955 =
0.02220 -0.00267 0.00033 0.00202
C10 1 0.565442 0.294931 0.084878 11.00000 0.02665 0.03690 =
0.03246 0.00579 0.00725 0.00735
AFIX 43
H10 2 0.641115 0.274303 0.138504 11.00000 -1.20000
AFIX 0
C16 1 -0.011769 0.347431 0.209809 11.00000 0.01863 0.04415 =
0.03016 -0.01217 0.00103 -0.00556
C2 1 0.348570 0.616393 0.374765 11.00000 0.01875 0.02991 =
0.03729 0.00054 0.00224 -0.00365
AFIX 23
H2A 2 0.427250 0.645549 0.357103 11.00000 -1.20000
H2B 2 0.336184 0.611273 0.492819 11.00000 -1.20000
AFIX 0
N1 5 0.268868 0.511736 0.321617 11.00000 0.01275 0.02778 =
0.02197 0.00229 -0.00016 -0.00139
C7 1 0.383279 0.447446 0.102414 11.00000 0.01956 0.02906 =
0.02885 0.00308 0.00558 0.00098
AFIX 23
H7A 2 0.314639 0.464662 0.023408 11.00000 -1.20000
H7B 2 0.471239 0.472407 0.101079 11.00000 -1.20000
AFIX 0
C15 1 0.087321 0.392713 0.188641 11.00000 0.02127 0.03057 =
0.02067 -0.00214 0.00254 0.00044
C17 1 -0.000714 0.309903 0.341167 11.00000 0.02546 0.02985 =
0.04157 -0.01003 0.01057 -0.00845
C12 1 0.379119 0.297127 -0.114758 11.00000 0.02521 0.04308 =
0.02985 -0.00750 0.00306 -0.00822
AFIX 43
H12 2 0.327115 0.277949 -0.199197 11.00000 -1.20000
AFIX 0
C3 1 0.210297 0.640907 0.301575 11.00000 0.03038 0.02916 =
0.03546 0.00205 0.00130 0.00258
AFIX 23
H3A 2 0.182086 0.678299 0.358033 11.00000 -1.20000
H3B 2 0.225342 0.650474 0.185948 11.00000 -1.20000
AFIX 0
C11 1 0.488309 0.266760 -0.036390 11.00000 0.03451 0.02794 =
0.03206 -0.00026 0.01104 0.00146
AFIX 43
H11 2 0.510387 0.226548 -0.065800 11.00000 -1.20000
AFIX 0
C9 1 0.531791 0.353309 0.127652 11.00000 0.01936 0.03539 =
0.02893 -0.00074 0.00260 -0.00281
AFIX 43
H9 2 0.586002 0.372763 0.209846 11.00000 -1.20000
AFIX 0
C13 1 0.345188 0.355477 -0.070604 11.00000 0.01969 0.04287 =
0.02838 0.00108 0.00478 0.00301
AFIX 43
H13 2 0.270025 0.376141 -0.125034 11.00000 -1.20000
AFIX 0
H1 2 0.261396 0.510512 0.424506 11.00000 0.03771
HKLF 4
REM OS2 recollect3 in P21/c #14
REM wR2 = 0.1225, GooF = S = 1.013, Restrained GooF = 1.013 for all data
REM R1 = 0.0556 for 2117 Fo > 4sig(Fo) and 0.0862 for all 2896 data
REM 239 parameters refined using 0 restraints
END
WGHT 0.0405 0.0000
REM Highest difference peak 0.299, deepest hole -0.249, 1-sigma level 0.059
Q1 1 0.2209 0.5282 0.5711 11.00000 0.05 0.30
Q2 1 0.2397 0.5006 0.5646 11.00000 0.05 0.28
Q3 1 0.2352 0.3727 0.3447 11.00000 0.05 0.27
Q4 1 0.3035 0.4694 0.7215 11.00000 0.05 0.25
Q5 1 0.3873 0.4505 0.3928 11.00000 0.05 0.25
;
_shelx_res_checksum 78547
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.24269(9) 0.51019(4) 0.68922(9) 0.0315(2) Uani d 1 . .
F F1 0.07331(19) 0.42667(8) 0.0555(2) 0.0327(5) Uani d 1 . .
F F5 0.31205(19) 0.36912(8) 0.53597(19) 0.0307(5) Uani d 1 . .
F F4 0.1190(2) 0.28212(8) 0.5801(2) 0.0404(5) Uani d 1 . .
F F2 -0.1166(2) 0.33964(10) 0.1010(2) 0.0474(6) Uani d 1 . .
F F3 -0.0977(2) 0.26613(9) 0.3625(2) 0.0492(6) Uani d 1 . .
C C14 0.1989(3) 0.40279(14) 0.2969(3) 0.0218(7) Uani d 1 . .
C C18 0.1081(4) 0.31807(14) 0.4497(4) 0.0281(8) Uani d 1 . .
C C6 0.3167(3) 0.44932(13) 0.2723(3) 0.0215(7) Uani d 1 . .
H H6 0.395538 0.438117 0.348882 0.026 Uiso calc 1 . .
C C5 0.1334(3) 0.53469(14) 0.2445(4) 0.0256(8) Uani d 1 . .
H H5A 0.055024 0.505280 0.260780 0.031 Uiso calc 1 . .
H H5B 0.148162 0.539641 0.126760 0.031 Uiso calc 1 . .
C C4 0.0922(3) 0.59416(15) 0.3182(4) 0.0308(8) Uani d 1 . .
H H4A 0.070518 0.588238 0.434277 0.037 Uiso calc 1 . .
H H4B 0.003969 0.609188 0.264765 0.037 Uiso calc 1 . .
C C8 0.4205(3) 0.38395(14) 0.0529(3) 0.0246(8) Uani d 1 . .
C C1 0.3883(3) 0.55697(14) 0.3002(4) 0.0267(8) Uani d 1 . .
H H1A 0.477032 0.541589 0.351631 0.032 Uiso calc 1 . .
H H1B 0.407412 0.562601 0.183476 0.032 Uiso calc 1 . .
C C19 0.2066(3) 0.36364(14) 0.4273(3) 0.0229(7) Uani d 1 . .
C C10 0.5654(4) 0.29493(15) 0.0849(4) 0.0320(8) Uani d 1 . .
H H10 0.641115 0.274303 0.138504 0.038 Uiso calc 1 . .
C C16 -0.0118(4) 0.34743(16) 0.2098(4) 0.0310(8) Uani d 1 . .
C C2 0.3486(3) 0.61639(15) 0.3748(4) 0.0286(8) Uani d 1 . .
H H2A 0.427250 0.645549 0.357103 0.034 Uiso calc 1 . .
H H2B 0.336184 0.611273 0.492819 0.034 Uiso calc 1 . .
N N1 0.2689(3) 0.51174(11) 0.3216(3) 0.0208(6) Uani d 1 . .
C C7 0.3833(3) 0.44745(14) 0.1024(3) 0.0258(8) Uani d 1 . .
H H7A 0.314639 0.464662 0.023408 0.031 Uiso calc 1 . .
H H7B 0.471239 0.472407 0.101079 0.031 Uiso calc 1 . .
C C15 0.0873(3) 0.39271(14) 0.1886(3) 0.0242(8) Uani d 1 . .
C C17 -0.0007(4) 0.30990(15) 0.3412(4) 0.0323(9) Uani d 1 . .
C C12 0.3791(4) 0.29713(16) -0.1148(4) 0.0327(9) Uani d 1 . .
H H12 0.327115 0.277949 -0.199197 0.039 Uiso calc 1 . .
C C3 0.2103(4) 0.64091(15) 0.3016(4) 0.0317(8) Uani d 1 . .
H H3A 0.182086 0.678299 0.358033 0.038 Uiso calc 1 . .
H H3B 0.225342 0.650474 0.185948 0.038 Uiso calc 1 . .
C C11 0.4883(4) 0.26676(15) -0.0364(4) 0.0315(9) Uani d 1 . .
H H11 0.510387 0.226548 -0.065800 0.038 Uiso calc 1 . .
C C9 0.5318(3) 0.35331(15) 0.1277(4) 0.0279(8) Uani d 1 . .
H H9 0.586002 0.372763 0.209846 0.033 Uiso calc 1 . .
C C13 0.3452(4) 0.35548(15) -0.0706(4) 0.0303(8) Uani d 1 . .
H H13 0.270025 0.376141 -0.125034 0.036 Uiso calc 1 . .
H H1 0.261(4) 0.5105(14) 0.425(4) 0.038(10) 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
Cl1 0.0238(5) 0.0421(5) 0.0286(4) 0.0016(4) 0.0007(4) 0.0024(4)
F1 0.0234(11) 0.0457(12) 0.0289(9) -0.0008(10) -0.0060(8) 0.0025(8)
F5 0.0222(11) 0.0387(12) 0.0313(9) -0.0010(9) -0.0049(8) 0.0063(8)
F4 0.0404(13) 0.0362(12) 0.0446(11) -0.0041(10) 0.0081(10) 0.0109(9)
F2 0.0290(12) 0.0668(15) 0.0464(11) -0.0172(11) -0.0084(10) -0.0126(10)
F3 0.0418(14) 0.0461(13) 0.0596(13) -0.0280(12) 0.0088(11) -0.0072(10)
C14 0.0128(17) 0.0257(17) 0.0271(16) 0.0031(15) 0.0054(14) -0.0046(13)
C18 0.030(2) 0.0277(19) 0.0271(17) 0.0013(17) 0.0061(16) 0.0021(14)
C6 0.0123(17) 0.0248(18) 0.0273(16) 0.0005(15) 0.0013(14) -0.0005(13)
C5 0.0143(18) 0.034(2) 0.0285(16) 0.0029(16) -0.0038(14) -0.0015(14)
C4 0.0173(19) 0.039(2) 0.0362(18) 0.0073(17) -0.0046(16) -0.0018(15)
C8 0.0188(18) 0.0282(18) 0.0268(16) -0.0001(16) 0.0079(15) 0.0034(14)
C1 0.0140(18) 0.033(2) 0.0329(18) -0.0044(16) 0.0020(15) 0.0030(14)
C19 0.0171(18) 0.0295(19) 0.0222(16) 0.0020(16) 0.0003(14) -0.0027(14)
C10 0.027(2) 0.037(2) 0.0325(18) 0.0074(18) 0.0072(16) 0.0058(16)
C16 0.0186(19) 0.044(2) 0.0302(18) -0.0056(18) 0.0010(16) -0.0122(16)
C2 0.0187(19) 0.0299(19) 0.0373(18) -0.0037(16) 0.0022(15) 0.0005(15)
N1 0.0128(15) 0.0278(15) 0.0220(14) -0.0014(13) -0.0002(12) 0.0023(12)
C7 0.0196(19) 0.0291(19) 0.0288(17) 0.0010(16) 0.0056(15) 0.0031(14)
C15 0.0213(19) 0.0306(19) 0.0207(16) 0.0004(16) 0.0025(14) -0.0021(14)
C17 0.025(2) 0.0299(19) 0.042(2) -0.0084(17) 0.0106(17) -0.0100(16)
C12 0.025(2) 0.043(2) 0.0299(18) -0.0082(19) 0.0031(16) -0.0075(16)
C3 0.030(2) 0.0292(19) 0.0355(18) 0.0026(17) 0.0013(17) 0.0020(15)
C11 0.035(2) 0.0279(19) 0.0321(19) 0.0015(18) 0.0110(17) -0.0003(15)
C9 0.0194(19) 0.035(2) 0.0289(17) -0.0028(16) 0.0026(15) -0.0007(14)
C13 0.0197(19) 0.043(2) 0.0284(17) 0.0030(17) 0.0048(15) 0.0011(15)
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
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
C15 C14 C19 . . 115.9(3) ?
C15 C14 C6 . . 124.2(3) ?
C19 C14 C6 . . 119.6(3) ?
F4 C18 C17 . . 120.1(3) ?
F4 C18 C19 . . 119.7(3) ?
C17 C18 C19 . . 120.2(3) ?
N1 C6 C14 . . 112.0(2) ?
N1 C6 C7 . . 113.0(2) ?
C14 C6 C7 . . 113.3(3) ?
N1 C6 H6 . . 105.9 ?
C14 C6 H6 . . 105.9 ?
C7 C6 H6 . . 105.9 ?
N1 C5 C4 . . 110.0(3) ?
N1 C5 H5A . . 109.7 ?
C4 C5 H5A . . 109.7 ?
N1 C5 H5B . . 109.7 ?
C4 C5 H5B . . 109.7 ?
H5A C5 H5B . . 108.2 ?
C5 C4 C3 . . 112.2(3) ?
C5 C4 H4A . . 109.2 ?
C3 C4 H4A . . 109.2 ?
C5 C4 H4B . . 109.2 ?
C3 C4 H4B . . 109.2 ?
H4A C4 H4B . . 107.9 ?
C9 C8 C13 . . 118.6(3) ?
C9 C8 C7 . . 120.7(3) ?
C13 C8 C7 . . 120.6(3) ?
C2 C1 N1 . . 110.8(2) ?
C2 C1 H1A . . 109.5 ?
N1 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
N1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 108.1 ?
F5 C19 C18 . . 117.7(3) ?
F5 C19 C14 . . 120.2(3) ?
C18 C19 C14 . . 122.1(3) ?
C9 C10 C11 . . 119.6(3) ?
C9 C10 H10 . . 120.2 ?
C11 C10 H10 . . 120.2 ?
F2 C16 C17 . . 120.4(3) ?
F2 C16 C15 . . 119.8(3) ?
C17 C16 C15 . . 119.7(3) ?
C1 C2 C3 . . 111.1(3) ?
C1 C2 H2A . . 109.4 ?
C3 C2 H2A . . 109.4 ?
C1 C2 H2B . . 109.4 ?
C3 C2 H2B . . 109.4 ?
H2A C2 H2B . . 108.0 ?
C5 N1 C1 . . 110.0(2) ?
C5 N1 C6 . . 116.4(2) ?
C1 N1 C6 . . 111.2(2) ?
C5 N1 H1 . . 111(2) ?
C1 N1 H1 . . 102(2) ?
C6 N1 H1 . . 105(2) ?
C8 C7 C6 . . 111.5(2) ?
C8 C7 H7A . . 109.3 ?
C6 C7 H7A . . 109.3 ?
C8 C7 H7B . . 109.3 ?
C6 C7 H7B . . 109.3 ?
H7A C7 H7B . . 108.0 ?
F1 C15 C16 . . 116.9(3) ?
F1 C15 C14 . . 120.6(3) ?
C16 C15 C14 . . 122.5(3) ?
F3 C17 C18 . . 120.7(3) ?
F3 C17 C16 . . 119.8(3) ?
C18 C17 C16 . . 119.5(3) ?
C11 C12 C13 . . 120.2(3) ?
C11 C12 H12 . . 119.9 ?
C13 C12 H12 . . 119.9 ?
C4 C3 C2 . . 109.3(3) ?
C4 C3 H3A . . 109.8 ?
C2 C3 H3A . . 109.8 ?
C4 C3 H3B . . 109.8 ?
C2 C3 H3B . . 109.8 ?
H3A C3 H3B . . 108.3 ?
C12 C11 C10 . . 119.9(3) ?
C12 C11 H11 . . 120.0 ?
C10 C11 H11 . . 120.0 ?
C10 C9 C8 . . 121.2(3) ?
C10 C9 H9 . . 119.4 ?
C8 C9 H9 . . 119.4 ?
C12 C13 C8 . . 120.4(3) ?
C12 C13 H13 . . 119.8 ?
C8 C13 H13 . . 119.8 ?
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
F1 C15 . 1.342(3) ?
F5 C19 . 1.335(3) ?
F4 C18 . 1.347(3) ?
F2 C16 . 1.338(4) ?
F3 C17 . 1.340(4) ?
C14 C15 . 1.388(4) ?
C14 C19 . 1.388(4) ?
C14 C6 . 1.523(4) ?
C18 C17 . 1.364(5) ?
C18 C19 . 1.380(4) ?
C6 N1 . 1.515(4) ?
C6 C7 . 1.538(4) ?
C6 H6 . 1.0000 ?
C5 N1 . 1.502(4) ?
C5 C4 . 1.507(4) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C4 C3 . 1.521(4) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C8 C9 . 1.385(4) ?
C8 C13 . 1.390(4) ?
C8 C7 . 1.512(4) ?
C1 C2 . 1.506(4) ?
C1 N1 . 1.511(4) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C10 C9 . 1.383(5) ?
C10 C11 . 1.382(5) ?
C10 H10 . 0.9500 ?
C16 C17 . 1.374(5) ?
C16 C15 . 1.378(4) ?
C2 C3 . 1.523(4) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
N1 H1 . 0.85(3) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C12 C11 . 1.381(5) ?
C12 C13 . 1.386(5) ?
C12 H12 . 0.9500 ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C11 H11 . 0.9500 ?
C9 H9 . 0.9500 ?
C13 H13 . 0.9500 ?
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 H1 Cl1 . 0.85(3) 2.20(3) 3.051(3) 178(3) yes