#------------------------------------------------------------------------------ #$Date: 2022-03-07 10:53:17 +0200 (Mon, 07 Mar 2022) $ #$Revision: 273487 $ #$URL: file:///home/coder/svn-repositories/cod/cif/8/10/46/8104659.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_8104659 loop_ _publ_author_name 'Atio\(glu, Zeliha' 'Karata\,s, Halis' 'K\"okbudak, Z\"ulbiye' _publ_section_title ; The crystal structure of 5-benzoyl-1-[(E)-(4-fluorobenzylidene)amino]-4-phenylpyrimidin-2(1H)-one, C24H16FN3O2 ; _journal_issue 5 _journal_name_full 'Zeitschrift f\"ur Kristallographie - New Crystal Structures' _journal_page_first 1035 _journal_page_last 1037 _journal_paper_doi 10.1515/ncrs-2021-0216 _journal_volume 236 _journal_year 2021 _chemical_formula_moiety 'C24 H16 F N3 O2' _chemical_formula_sum 'C24 H16 F N3 O2' _chemical_formula_weight 397.40 _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 _cell_angle_alpha 90 _cell_angle_beta 91.750(9) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 6.0024(5) _cell_length_b 19.474(2) _cell_length_c 8.3531(8) _cell_measurement_reflns_used 1069 _cell_measurement_temperature 294(2) _cell_measurement_theta_max 22.4200 _cell_measurement_theta_min 4.0060 _cell_volume 975.94(16) _computing_cell_refinement 'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019) [1]' _computing_data_collection 'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019) [1]' _computing_data_reduction 'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019) [1]' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 2012) [4]' _computing_publication_material 'PLATON (Spek, 2009) [5]' _computing_structure_refinement 'SHELXL2018/3 (Sheldrick, 2015b) [3]' _computing_structure_solution 'SHELXT2014/5 (Sheldrick, 2015a) [2]' _diffrn_ambient_temperature 294(2) _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0943408000 _diffrn_orient_matrix_UB_12 -0.0211627000 _diffrn_orient_matrix_UB_13 0.0156322000 _diffrn_orient_matrix_UB_21 0.0698213000 _diffrn_orient_matrix_UB_22 0.0255793000 _diffrn_orient_matrix_UB_23 -0.0321847000 _diffrn_orient_matrix_UB_31 0.0140158000 _diffrn_orient_matrix_UB_32 0.0149849000 _diffrn_orient_matrix_UB_33 0.0770707000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_unetI/netI 0.0518 _diffrn_reflns_Laue_measured_fraction_full 0.992 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 3430 _diffrn_reflns_point_group_measured_fraction_full 0.638 _diffrn_reflns_point_group_measured_fraction_max 0.638 _diffrn_reflns_theta_full 25.026 _diffrn_reflns_theta_max 25.026 _diffrn_reflns_theta_min 3.214 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_correction_T_min 0.980 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.352 _exptl_crystal_description prism _exptl_crystal_F_000 412 _exptl_crystal_size_max 0.303 _exptl_crystal_size_mid 0.278 _exptl_crystal_size_min 0.215 _refine_diff_density_max 0.131 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.036 _refine_ls_abs_structure_details ; Flack x determined using 328 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 271 _refine_ls_number_reflns 2195 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.010 _refine_ls_R_factor_all 0.0631 _refine_ls_R_factor_gt 0.0409 _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^)+(0.0302P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0733 _refine_ls_wR_factor_ref 0.0832 _reflns_Friedel_coverage 0.246 _reflns_Friedel_fraction_full 0.260 _reflns_Friedel_fraction_max 0.260 _reflns_number_gt 1680 _reflns_number_total 2195 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file suppl_j_ncrs-2021-0216_suppl.cif _cod_data_source_block ZKK-12 _cod_original_cell_volume 975.92(17) _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 8104659 _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_res_file ; TITL ZKK-12 in P2(1) shelx.res created by SHELXL-2018/3 at 07:44:19 on 12-Dec-2020 CELL 0.71073 6.0024 19.4736 8.3531 90.000 91.750 90.000 ZERR 2.00 0.0005 0.0023 0.0008 0.000 0.009 0.000 LATT -1 SYMM - X, 1/2 + Y, - Z SFAC C H F N O UNIT 48 32 2 6 4 MERG 2 MORE -1 FMAP 2 53 53 PLAN 5 ACTA BOND BOND $H CONF LIST 4 L.S. 13 WGHT 0.030200 FVAR 11.01865 F1 3 -0.420734 0.287381 0.108709 11.00000 0.06612 0.09154 = 0.07740 -0.00840 -0.03222 -0.01502 O1 5 0.633247 0.345820 0.725052 11.00000 0.05672 0.04691 = 0.05859 0.01672 -0.00962 -0.01459 O2 5 1.253245 0.558680 0.450041 11.00000 0.03404 0.06071 = 0.08272 0.02574 0.00227 0.00184 N1 4 0.893361 0.429810 0.751835 11.00000 0.03841 0.03871 = 0.04547 0.00152 -0.00384 -0.00392 N2 4 0.627957 0.431140 0.535362 11.00000 0.03830 0.03288 = 0.04088 0.00230 -0.00287 -0.00066 N3 4 0.448361 0.408858 0.436118 11.00000 0.03792 0.03770 = 0.04951 0.00030 -0.00643 -0.00342 C1 1 0.308538 0.366788 0.489431 11.00000 0.04083 0.04352 = 0.04518 0.00151 -0.00097 0.00202 AFIX 43 H1 2 0.324181 0.349847 0.593261 11.00000 -1.20000 AFIX 0 C2 1 0.120754 0.345137 0.384275 11.00000 0.03801 0.03418 = 0.04263 -0.00661 -0.00110 0.00323 C3 1 0.085874 0.372567 0.231754 11.00000 0.05232 0.04180 = 0.04796 0.00669 0.00236 -0.00288 AFIX 43 H3 2 0.186226 0.404403 0.192823 11.00000 -1.20000 AFIX 0 C4 1 -0.095595 0.353053 0.137991 11.00000 0.06137 0.05884 = 0.04196 0.00087 -0.01311 0.00722 AFIX 43 H4 2 -0.120613 0.371454 0.036286 11.00000 -1.20000 AFIX 0 C5 1 -0.238083 0.305663 0.199345 11.00000 0.04424 0.05575 = 0.05444 -0.01354 -0.01657 0.00396 C6 1 -0.209292 0.276551 0.345797 11.00000 0.04473 0.05251 = 0.05473 0.00110 -0.00323 -0.01081 AFIX 43 H6 2 -0.309460 0.244095 0.382256 11.00000 -1.20000 AFIX 0 C7 1 -0.026648 0.296473 0.439583 11.00000 0.04702 0.04411 = 0.04385 -0.00026 -0.00442 0.00041 AFIX 43 H7 2 -0.002663 0.277079 0.540383 11.00000 -1.20000 AFIX 0 C8 1 0.715874 0.397722 0.675379 11.00000 0.04030 0.04091 = 0.04181 0.00616 0.00054 0.00105 C9 1 0.990678 0.483595 0.692063 11.00000 0.03361 0.03563 = 0.04291 -0.00246 0.00085 0.00462 C10 1 1.177889 0.512480 0.791783 11.00000 0.04162 0.03932 = 0.04261 -0.00242 -0.00117 0.00077 C11 1 1.221966 0.582110 0.799870 11.00000 0.05972 0.04225 = 0.06266 -0.00390 -0.01348 0.00241 AFIX 43 H11 2 1.132344 0.612730 0.741724 11.00000 -1.20000 AFIX 0 C12 1 1.398143 0.606505 0.893688 11.00000 0.07712 0.05150 = 0.07609 -0.00747 -0.01434 -0.02065 AFIX 43 H12 2 1.426222 0.653441 0.898224 11.00000 -1.20000 AFIX 0 C13 1 1.531292 0.562331 0.979742 11.00000 0.05374 0.07368 = 0.06771 -0.01599 -0.01448 -0.01097 AFIX 43 H13 2 1.652549 0.578989 1.039870 11.00000 -1.20000 AFIX 0 C14 1 1.485963 0.493210 0.977433 11.00000 0.05705 0.05922 = 0.06080 -0.00131 -0.01839 0.00507 AFIX 43 H14 2 1.573843 0.463213 1.038699 11.00000 -1.20000 AFIX 0 C15 1 1.309874 0.468134 0.884166 11.00000 0.05169 0.04254 = 0.05310 -0.00065 -0.00901 0.00310 AFIX 43 H15 2 1.279576 0.421298 0.883255 11.00000 -1.20000 AFIX 0 C16 1 0.733406 0.485305 0.472921 11.00000 0.04031 0.02960 = 0.04214 0.00593 0.00058 0.00459 AFIX 43 H16 2 0.676756 0.504300 0.377982 11.00000 -1.20000 AFIX 0 C17 1 0.919168 0.513472 0.542590 11.00000 0.03252 0.03225 = 0.04042 0.00414 -0.00045 0.00164 C18 1 1.050938 0.563873 0.450609 11.00000 0.03815 0.03327 = 0.04779 0.00037 -0.00328 -0.00209 C19 1 0.935203 0.618759 0.355291 11.00000 0.03350 0.04102 = 0.03672 0.00294 -0.00289 -0.00352 C20 1 1.045169 0.647359 0.229590 11.00000 0.04880 0.05626 = 0.05795 0.01189 -0.00169 -0.00673 AFIX 43 H20 2 1.185055 0.630978 0.203635 11.00000 -1.20000 AFIX 0 C21 1 0.949092 0.700295 0.141590 11.00000 0.08570 0.06190 = 0.05199 0.02413 -0.00597 -0.00805 AFIX 43 H21 2 1.023022 0.719103 0.055728 11.00000 -1.20000 AFIX 0 C22 1 0.742377 0.725148 0.181922 11.00000 0.07807 0.03609 = 0.06336 0.00734 -0.02553 0.00077 AFIX 43 H22 2 0.678019 0.761289 0.124294 11.00000 -1.20000 AFIX 0 C23 1 0.634144 0.696932 0.304919 11.00000 0.04943 0.03478 = 0.07357 -0.00259 -0.01466 0.00640 AFIX 43 H23 2 0.494585 0.713686 0.330536 11.00000 -1.20000 AFIX 0 C24 1 0.727072 0.643388 0.393943 11.00000 0.04329 0.03372 = 0.04989 0.00264 0.00114 -0.00384 AFIX 43 H24 2 0.650722 0.624309 0.478349 11.00000 -1.20000 AFIX 0 HKLF 4 REM ZKK-12 in P2(1) REM wR2 = 0.0832, GooF = S = 1.010, Restrained GooF = 1.010 for all data REM R1 = 0.0409 for 1680 Fo > 4sig(Fo) and 0.0631 for all 2195 data REM 271 parameters refined using 1 restraints END WGHT 0.0302 0.0000 REM Highest difference peak 0.131, deepest hole -0.199, 1-sigma level 0.036 Q1 1 0.5558 0.4206 0.4793 11.00000 0.05 0.13 Q2 1 0.8576 0.4016 0.4454 11.00000 0.05 0.13 Q3 1 0.6155 0.5176 0.3087 11.00000 0.05 0.13 Q4 1 0.5771 0.5230 0.6195 11.00000 0.05 0.13 Q5 1 1.8189 0.6006 1.0385 11.00000 0.05 0.12 ; _shelx_res_checksum 32040 _shelx_hkl_file ; 0 -23 0-522.185 703.605 4 0 -23 -1-949.260 845.491 4 0 -22 0 8581.48 1551.42 4 0 -22 -1 1036.12 648.232 4 0 -22 -2 28.1983 510.024 4 0 -22 -3 908.648 540.917 4 0 -21 0-1654.63 822.540 4 0 -21 -1 5756.72 1200.58 4 0 -21 -2 3941.70 1018.40 4 0 -21 -3 2870.59 912.635 4 0 -21 -4 4484.61 1138.83 4 0 -20 0 1063.92 505.443 4 0 -20 -1 134.252 475.870 4 0 -20 -2 1740.58 669.941 4 0 -20 -3 6100.17 1211.22 4 0 -20 -4 2344.24 803.703 4 0 -20 -5-659.808 559.805 4 0 -19 0-578.121 648.051 4 0 -19 -1 618.581 620.734 4 0 -19 -2-212.116 469.349 4 0 -19 -3 2466.15 742.318 4 0 -19 -4 4239.89 1061.46 4 0 -19 -5 919.147 502.470 4 0 -18 0 4234.79 973.043 4 0 -18 -1 314.042 423.662 4 0 -18 1 406.271 495.279 4 0 -18 -2 1825.28 558.669 4 0 -18 -3 4812.63 1020.06 4 0 -18 -4 4595.06 1047.13 4 0 -18 -5 319.326 451.968 4 0 -18 -6 871.076 559.230 4 0 -17 0-524.423 593.977 4 0 -17 1 358.520 518.063 4 0 -17 -1 927.890 571.962 4 0 -17 -2 1896.46 737.695 4 0 -17 -3 6703.63 1122.51 4 0 -17 -4 5035.57 1027.03 4 0 -17 -5 885.850 596.535 4 0 -17 -6 944.091 596.799 4 0 -16 0 8957.99 1322.28 4 0 -16 -1 2092.24 777.409 4 0 -16 1 2845.71 811.466 4 0 -16 -2 12205.4 1469.62 4 0 -16 -3 3211.08 807.976 4 0 -16 -4 14324.0 1583.23 4 0 -16 -5 1123.45 486.980 4 0 -16 6 1208.06 872.958 2 0 -16 -6 592.484 446.048 4 0 -16 7 1106.36 846.476 2 0 -16 -7 1216.29 562.321 4 0 -15 0 843.582 618.888 4 0 -15 1 12005.8 1460.33 4 0 -15 -1 10514.2 1269.26 4 0 -15 -2 3899.71 873.839 4 0 -15 -3 26901.2 2045.02 4 0 -15 -4 7167.03 1146.41 4 0 -15 -5 346.649 365.290 4 0 -15 6 6120.85 1381.29 2 0 -15 -6 4392.98 943.129 4 0 -15 -7 1129.85 601.788 4 0 -15 7 1719.40 839.419 2 0 -14 0 166324. 4858.12 4 0 -14 1 24665.7 1980.60 4 0 -14 -1 22909.9 1788.00 4 0 -14 -2 6268.49 969.001 4 0 -14 -3 43491.3 2444.94 4 0 -14 -4 18468.0 1666.63 4 0 -14 -5 8201.73 1175.46 4 0 -14 -6 1159.96 443.523 4 0 -14 6 1450.57 983.523 2 0 -14 -7 6610.81 1134.10 4 0 -14 7 8079.65 1611.47 2 0 -13 0-161.878 511.937 4 0 -13 -1 12423.9 1285.36 4 0 -13 1 12670.3 1350.00 4 0 -13 -2 7645.27 1020.05 4 0 -13 -3 22311.6 1692.11 4 0 -13 -4 47919.3 2549.72 4 0 -13 -5 20111.1 1717.27 4 0 -13 -6-225.861 349.665 4 0 -13 6-381.315 697.710 2 0 -13 7 1319.44 634.577 2 0 -13 -7 2223.97 655.045 4 0 -13 -8 1662.75 640.162 4 0 -13 8 886.120 674.648 2 0 -12 0 1049.48 567.143 4 0 -12 1 4756.85 895.436 4 0 -12 -1 4842.75 845.215 4 0 -12 -2 11486.3 1209.86 4 0 -12 -3 727.878 444.492 4 0 -12 -4 15746.3 1407.77 4 0 -12 -5 8381.52 1093.24 4 0 -12 -6 767.968 366.855 4 0 -12 6 1189.09 898.168 2 0 -12 7 1543.23 962.043 2 0 -12 -7 1493.39 591.243 4 0 -12 -8 6255.50 1097.22 4 0 -12 8 6607.73 1435.92 2 0 -11 0 176.251 378.409 4 0 -11 1 87385.7 3190.26 4 0 -11 -1 92712.2 3130.23 4 0 -11 -2 216.631 328.485 4 0 -11 -3 525.433 439.870 4 0 -11 -4 47362.1 2331.74 4 0 -11 5 79805.6 3796.47 2 0 -11 -5 84180.8 3207.02 4 0 -11 6 9639.19 1466.71 2 0 -11 -6 10560.4 1252.94 4 0 -11 7-692.583 781.556 2 0 -11 -7 96.7295 303.090 4 0 -11 -8 7198.13 1171.45 4 0 -11 8 8290.86 1538.47 2 0 -10 0 24214.9 1511.36 4 0 -10 1 16598.9 1332.82 4 0 -10 -1 14085.6 1181.38 4 0 -10 -2 15884.5 1266.38 4 0 -10 -3 1134.21 424.330 4 0 -10 -4 2864.35 614.471 4 0 -10 -5 14553.5 1334.48 4 0 -10 5 13237.4 1614.79 2 0 -10 -6 6564.13 965.736 4 0 -10 6 7639.26 1340.28 2 0 -10 -7-47.6565 336.791 4 0 -10 7 85.5864 546.792 2 0 -10 -8 8030.10 1172.64 4 0 -10 8 6896.91 1338.97 2 0 -9 0-73.3484 339.045 4 0 -9 1 25085.4 1540.37 4 0 -9 -1 23682.8 1417.26 4 0 -9 -2 4781.68 679.638 4 0 -9 -3 5783.26 779.773 4 0 -9 -4 970.584 411.710 4 0 -9 5 1094.28 712.019 2 0 -9 -5 231.730 345.510 4 0 -9 -6 5980.70 883.011 4 0 -9 6 4276.63 1022.37 2 0 -9 -7 1759.44 529.139 4 0 -9 7 2436.19 816.577 2 0 -9 -8 1689.57 581.930 4 0 -9 8 670.477 707.295 2 0 -9 -8 1217.25 544.388 3 0 -9 -9 6462.48 1086.43 4 0 -9 -9 5947.33 1134.51 3 0 -8 0 6524.29 746.762 4 0 -8 -1 55748.5 2003.67 4 0 -8 1 56575.5 2206.80 4 0 -8 -2 26586.4 1413.89 4 0 -8 -3 10881.1 947.363 4 0 -8 -4 2142.62 495.320 4 0 -8 5 6738.73 1137.95 2 0 -8 -5 5978.29 814.741 4 0 -8 -6 12331.9 1238.23 4 0 -8 6 11290.4 1477.22 2 0 -8 -7 9885.59 1174.44 4 0 -8 7 10972.2 1522.84 2 0 -8 -8 3276.59 760.891 3 0 -8 -8 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536.753 2 3 -5 -3 7189.09 1026.54 4 3 -5 -2 19323.8 644.939 2 3 -5 -2 21868.5 1580.25 4 -3 -5 2 19274.8 1350.52 1 3 -5 -1 11362.0 981.640 3 3 -5 -1 11409.9 1106.87 4 -3 -5 1 12553.7 982.655 1 -3 -5 0 10056.4 810.655 1 3 -5 0 9288.66 474.543 2 3 -5 0 10060.5 986.512 3 3 -5 0 9911.83 1015.18 4 3 -5 1 366.352 322.056 4 3 -5 1 724.578 439.907 3 3 -5 1 618.115 245.857 2 -3 -5 -2 2918.06 650.840 3 3 -5 2 3471.41 600.286 4 -3 -5 -3 10124.8 1224.56 3 3 -5 3 9971.22 991.495 4 3 -5 4 5408.00 619.949 1 -3 -5 -4 5140.47 995.865 3 -3 -5 -5 22093.6 1978.74 3 3 -5 5 26101.7 1364.22 1 -3 -5 -6 7305.03 768.340 1 -3 -5 -6 6423.19 1173.66 3 -3 -5 -7 2646.78 568.443 1 -3 -5 -7 2092.53 809.163 3 -3 -5 -8 3237.50 1120.43 3 3 -4 -8 6178.42 1326.76 1 3 -4 -7 18924.8 1990.52 1 3 -4 -6 6291.44 429.134 3 -3 -4 6 7147.41 1044.78 2 3 -4 -5 14659.2 1197.60 2 -3 -4 5 16784.7 1484.30 2 -3 -4 4 16017.4 1303.02 2 3 -4 -4 14699.5 1004.55 2 3 -4 -3 20391.5 935.067 2 -3 -4 3 21039.1 729.218 3 3 -4 -2 1364.71 473.789 4 -3 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1067.51 4 -5 -2 1 7751.50 960.475 3 5 -2 0 12815.4 1224.08 4 5 -2 0 11557.8 905.748 1 -5 -2 0 10408.1 1174.18 3 5 -2 1 9739.74 646.922 1 5 -2 1 10310.6 1066.34 4 -5 -2 -1 10608.6 1273.43 3 5 -2 2 7077.86 824.650 4 -5 -2 -2 8171.55 1246.08 3 -5 -2 -3 4183.89 960.466 3 5 -2 3 5704.39 701.567 4 -5 -2 -4 3120.90 840.028 3 -5 -2 -5 8943.50 1525.52 3 -5 -2 -6 1289.89 731.635 3 5 -1 -7 1807.58 767.591 1 5 -1 -6 779.244 687.073 1 5 -1 -5 573.179 499.981 1 5 -1 -4 277.011 400.633 1 5 -1 -3 2412.16 683.229 1 5 -1 -2 383.696 347.315 1 5 -1 -1 1301.34 507.773 1 5 -1 -1 688.791 440.650 4 -5 -1 1 1166.52 494.176 3 5 -1 0 1147.56 427.982 4 -5 -1 0 1681.42 621.337 3 5 -1 0 1438.24 412.360 1 5 -1 1 10869.8 1032.01 4 -5 -1 -1 9886.21 1224.96 3 -5 -1 -2 1412.43 727.665 3 5 -1 2 1160.27 347.116 4 -5 -1 -2 1924.44 442.915 2 5 -1 3 3929.33 522.820 4 -5 -1 -3 4255.36 959.154 3 -5 -1 -4 9776.64 1492.33 3 -5 -1 -5-910.595 880.186 3 -5 -1 -6 4370.23 1204.77 3 5 0 -7 2079.23 816.931 1 5 0 -6 1823.06 825.167 1 5 0 -5 967.246 649.453 1 5 0 -4-891.313 607.944 1 5 0 -3 189.660 408.174 1 5 0 -2 8839.63 1056.21 1 5 0 -1 298.165 309.093 4 5 0 -1-86.6865 378.038 1 -5 0 0 3591.61 304.488 2 5 0 0 4068.32 674.628 4 -5 0 0 4822.46 866.283 3 -5 0 -1 5040.94 531.104 2 5 0 1 6009.12 760.445 4 -5 0 -1 4388.59 854.137 3 -5 0 -2 922.460 338.135 2 5 0 2 465.319 265.518 4 -5 0 -2 917.457 666.060 3 -5 0 -3-596.017 668.442 3 -5 0 -4 261.592 641.973 3 -5 0 -5 12372.6 1775.15 3 -5 0 -6 842.674 913.878 3 5 1 -7 1434.99 874.912 1 5 1 -6 1447.30 919.310 1 5 1 -5 929.761 571.831 1 5 1 -4 613.933 489.150 1 5 1 -3 1772.36 626.555 1 5 1 -2 149.171 438.067 1 5 1 0 2003.75 511.754 4 -5 1 -1 10163.3 709.456 2 5 1 1 9387.07 885.761 4 -5 1 -1 8669.14 1236.57 3 5 1 2 1748.87 353.102 4 -5 1 -2 1355.58 570.931 3 -5 1 -3 4254.12 707.281 2 -5 1 -3 3671.89 925.045 3 -5 1 -4 10870.6 1668.35 3 -5 1 -5 1094.62 863.307 3 -5 1 -6 1038.27 682.129 3 5 2 -7-837.358 671.351 1 5 2 -6 233.908 556.842 1 5 2 -5 3761.99 948.101 1 5 2 -4 3898.85 928.365 1 5 2 -3 4276.38 860.081 1 5 2 0 11967.9 1077.81 4 5 2 1 10711.5 891.537 4 -5 2 -2 7682.12 1246.85 3 5 2 2 5904.82 556.948 4 -5 2 -3 4278.62 706.316 2 -5 2 -3 4768.80 1023.73 3 -5 2 -4 3943.00 932.050 3 -5 2 -5 8446.79 1475.42 3 -5 2 -6 2008.42 1030.05 3 5 3 1 206.894 245.820 4 5 3 2 5052.73 460.764 4 -5 3 -3 352.732 652.165 3 -5 3 -4 10197.0 1590.24 3 -5 3 -5 2521.43 943.020 3 -5 3 -6-290.493 671.141 3 5 4 1 15344.2 1008.33 4 5 5 1 24969.2 1257.09 4 6 -12 -1 8245.98 1486.14 4 -6 -12 0 1157.01 569.858 3 6 -12 0 708.444 550.185 4 -6 -12 -1 1034.43 588.874 3 6 -12 1 771.382 650.289 4 6 -11 -2 454.292 439.485 4 6 -11 -1 1527.96 724.732 4 -6 -11 0 2877.42 814.874 3 6 -11 0 5974.84 1214.42 4 -6 -11 -1 6154.09 1216.85 3 6 -11 1 6319.79 1197.10 4 -6 -11 -2 746.902 603.165 3 6 -11 2-81.5260 394.814 4 6 -10 -3 2457.20 924.026 4 6 -10 -2 525.521 491.779 4 6 -10 -1 5687.14 1215.10 4 -6 -10 0 1254.34 601.233 3 6 -10 0 493.734 508.158 4 -6 -10 -1 4359.64 1032.41 3 6 -10 1 2930.59 866.197 4 -6 -10 -2 786.195 560.806 3 6 -10 2 682.570 475.661 4 -6 -10 -3 1195.49 728.986 3 6 -9 -4 1037.30 524.867 4 6 -9 -3 3222.77 961.427 4 6 -9 -2 2156.62 854.444 4 -6 -9 1 1250.61 609.436 3 6 -9 -1 195.933 400.419 4 -6 -9 0 1084.22 488.927 3 6 -9 0 2927.85 890.401 4 -6 -9 -1-5.89063 522.521 3 6 -9 1 774.816 552.072 4 -6 -9 -2 5404.05 1177.32 3 6 -9 2 5314.72 1073.23 4 -6 -9 -3 2243.35 822.335 3 6 -8 -4 1145.87 718.062 4 6 -8 -3 1855.35 831.556 4 6 -8 -2-337.060 598.423 4 -6 -8 1 1275.10 595.042 3 6 -8 -1 758.008 577.318 4 -6 -8 0 1247.43 540.489 3 6 -8 0 1976.23 723.548 4 -6 -8 -1 797.853 459.863 3 6 -8 1 1015.72 569.534 4 -6 -8 -2 820.813 639.985 3 6 -8 2 1268.47 614.380 4 -6 -8 -3 499.887 729.055 3 6 -7 -4 169.991 431.247 4 6 -7 -3 5275.52 1121.40 4 6 -7 -2 276.626 548.189 4 -6 -7 1 735.344 433.573 3 6 -7 -1 716.977 544.998 4 -6 -7 0 924.749 533.180 3 6 -7 0 797.846 508.836 4 -6 -7 -1 6406.58 1133.86 3 6 -7 1 6023.90 1003.25 4 -6 -7 -2 1137.57 586.311 3 6 -7 2 1327.77 627.380 4 -6 -7 -3 2384.65 932.428 3 -6 -7 -4 2610.20 911.521 3 6 -6 -5 645.760 548.329 1 6 -6 -5-363.818 539.388 4 6 -6 -4 1217.46 508.367 1 6 -6 -4 2639.82 893.602 4 6 -6 -3 267.143 491.486 4 6 -6 -2 2458.48 825.114 4 6 -6 -1 2914.27 833.282 4 -6 -6 1 3432.53 737.374 3 -6 -6 0 2258.21 625.094 3 6 -6 0 2069.37 657.433 4 -6 -6 -1 2874.36 800.788 3 6 -6 1 2614.02 711.622 4 -6 -6 -2 733.317 594.521 3 6 -6 2 869.501 452.365 4 -6 -6 -3 395.888 557.205 3 -6 -6 -4 211.656 628.403 3 6 -5 -5-464.487 596.319 4 6 -5 -5-335.373 517.176 1 6 -5 -4 3235.13 881.188 1 6 -5 -4 1896.41 728.366 4 6 -5 -3 4930.42 1080.87 4 6 -5 -3 4682.54 936.796 1 6 -5 -2 14234.9 1666.69 4 6 -5 -2 13130.3 1382.17 1 6 -5 -1 1890.73 531.804 1 6 -5 -1 1449.89 593.218 4 -6 -5 1 1925.04 554.576 3 6 -5 0 1851.12 605.493 4 -6 -5 0 2260.32 584.266 3 -6 -5 -1 4464.93 887.325 3 6 -5 1 6723.09 1048.43 4 -6 -5 -2 960.677 577.272 3 -6 -5 -3 1193.28 737.545 3 -6 -5 -4-90.9054 578.086 3 6 -4 -5-299.865 466.677 1 6 -4 -5 670.642 607.096 4 6 -4 -4 1247.42 579.589 1 6 -4 -4 1846.52 752.697 4 6 -4 -3 5826.94 1120.36 4 6 -4 -3 4966.86 941.663 1 6 -4 -2 5607.97 1064.55 4 6 -4 -2 6107.06 962.911 1 6 -4 -1 999.777 451.276 1 6 -4 -1 2136.02 715.334 4 -6 -4 1 758.118 438.214 3 6 -4 0 3449.69 805.197 4 -6 -4 0 5918.74 1023.97 3 -6 -4 -1 363.634 449.951 3 6 -4 1 567.306 355.567 4 -6 -4 -2 2679.35 949.898 3 -6 -4 -3 3661.50 968.977 3 -6 -4 -4 2308.66 942.731 3 6 -3 -5-72.2090 524.806 4 6 -3 -5 974.074 574.376 1 6 -3 -4 1477.91 781.011 4 6 -3 -4 265.827 499.175 1 6 -3 -3 2395.81 816.302 4 6 -3 -3 1970.78 648.572 1 6 -3 -2 935.857 592.221 4 6 -3 -2 1062.71 483.272 1 6 -3 -1 5163.98 967.148 4 6 -3 -1 3509.49 704.593 1 -6 -3 1 3142.47 689.940 3 6 -3 0 5863.67 947.693 4 -6 -3 0 5086.47 950.206 3 6 -3 1 2563.14 621.551 4 -6 -3 -1 2477.26 786.728 3 -6 -3 -2 6035.84 1117.25 3 -6 -3 -3 5405.87 1168.30 3 -6 -3 -4 1278.99 758.088 3 6 -2 -5-193.172 621.597 1 6 -2 -4 1501.42 661.768 1 6 -2 -4 899.175 518.800 4 6 -2 -3 4783.54 914.371 1 6 -2 -3 5893.85 1125.16 4 6 -2 -2 17858.6 1590.90 1 6 -2 -2 17019.8 1718.07 4 6 -2 -1 15595.1 1323.23 1 6 -2 -1 18832.1 1729.18 4 -6 -2 1 15657.7 1455.13 3 6 -2 0-88.7781 309.275 4 -6 -2 0 153.978 404.786 3 6 -2 1 9582.19 1108.58 4 -6 -2 -1 9127.27 1328.19 3 -6 -2 -2-83.3086 591.027 3 -6 -2 -3 1449.10 801.014 3 -6 -2 -4 4439.62 1169.24 3 -6 -2 -5 188.833 600.096 3 6 -1 -5 949.669 664.268 1 6 -1 -4-240.198 493.280 1 6 -1 -3 1249.79 608.273 1 6 -1 -3 290.509 498.724 4 6 -1 -2 3381.87 809.557 4 6 -1 -2 1875.96 572.211 1 6 -1 -1 12161.2 1166.64 1 6 -1 -1 14086.4 1500.27 4 6 -1 0 7716.52 1046.67 4 -6 -1 0 7138.77 1161.16 3 6 -1 1 2001.87 541.814 4 -6 -1 -1 881.614 527.478 3 -6 -1 -2 8146.71 1313.05 3 -6 -1 -3 2348.62 889.292 3 -6 -1 -4 1984.20 833.951 3 -6 -1 -5 3614.71 1161.68 3 6 0 -5-736.708 811.844 1 6 0 -4 279.910 621.696 1 6 0 -3 2655.17 745.975 1 6 0 -2 844.415 539.030 4 6 0 -2 846.864 454.407 1 6 0 -1 341.664 408.561 4 6 0 0 12092.2 1239.69 4 -6 0 -1 7520.83 1224.85 3 -6 0 -2 2434.44 858.485 3 -6 0 -3 4308.17 1108.80 3 -6 0 -4 3242.16 1037.04 3 -6 0 -5 1768.23 916.280 3 6 1 -5 1494.54 675.594 1 6 1 -4 146.483 422.120 1 6 1 -3-734.126 512.886 1 6 1 -1 15715.9 1533.67 4 6 1 0 6496.64 893.771 4 -6 1 -2 6531.33 1282.80 3 -6 1 -3 1685.64 761.889 3 -6 1 -4 867.664 717.802 3 -6 1 -5 1163.05 763.671 3 6 2 -1 15819.0 1467.00 4 6 2 0 520.402 295.880 4 -6 2 -4 3915.96 1087.95 3 -6 2 -5-353.031 808.273 3 6 3 0 6585.33 875.403 4 7 -4 -1-247.404 367.306 4 7 -3 -1 135.669 348.152 4 -7 -3 -1 595.369 711.927 3 7 -2 -2 3925.54 935.538 4 7 -2 -1 2679.89 773.405 4 -7 -2 -1 707.059 623.169 3 7 -1 -2 419.350 368.442 4 -7 -1 -1 2071.60 885.493 3 7 0 -2 1220.01 655.346 4 7 1 -2-87.3530 400.567 4 7 2 -2 4475.77 951.481 4 0 0 0 0.00 0.00 0 ; _shelx_hkl_checksum 27227 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group F1 F -0.4207(4) 0.28738(16) 0.1087(3) 0.0791(9) Uani 1 1 d . . . . . O1 O 0.6332(4) 0.34582(17) 0.7251(3) 0.0543(9) Uani 1 1 d . . . . . O2 O 1.2532(4) 0.55868(17) 0.4500(4) 0.0591(9) Uani 1 1 d . . . . . N1 N 0.8934(5) 0.42981(19) 0.7518(4) 0.0410(9) Uani 1 1 d . . . . . N2 N 0.6280(5) 0.43114(17) 0.5354(4) 0.0374(9) Uani 1 1 d . . . . . N3 N 0.4484(5) 0.40886(18) 0.4361(4) 0.0419(9) Uani 1 1 d . . . . . C1 C 0.3085(6) 0.3668(2) 0.4894(5) 0.0432(11) Uani 1 1 d . . . . . H1 H 0.324181 0.349847 0.593261 0.052 Uiso 1 1 calc R U . . . C2 C 0.1208(6) 0.3451(2) 0.3843(5) 0.0383(10) Uani 1 1 d . . . . . C3 C 0.0859(7) 0.3726(2) 0.2318(5) 0.0473(12) Uani 1 1 d . . . . . H3 H 0.186226 0.404403 0.192823 0.057 Uiso 1 1 calc R U . . . C4 C -0.0956(7) 0.3531(3) 0.1380(5) 0.0544(13) Uani 1 1 d . . . . . H4 H -0.120613 0.371454 0.036286 0.065 Uiso 1 1 calc R U . . . C5 C -0.2381(7) 0.3057(3) 0.1993(5) 0.0518(13) Uani 1 1 d . . . . . C6 C -0.2093(6) 0.2766(3) 0.3458(5) 0.0508(13) Uani 1 1 d . . . . . H6 H -0.309460 0.244095 0.382256 0.061 Uiso 1 1 calc R U . . . C7 C -0.0266(6) 0.2965(2) 0.4396(5) 0.0451(11) Uani 1 1 d . . . . . H7 H -0.002663 0.277079 0.540383 0.054 Uiso 1 1 calc R U . . . C8 C 0.7159(6) 0.3977(3) 0.6754(5) 0.0410(11) Uani 1 1 d . . . . . C9 C 0.9907(6) 0.4836(2) 0.6921(5) 0.0374(10) Uani 1 1 d . . . . . C10 C 1.1779(6) 0.5125(2) 0.7918(5) 0.0412(11) Uani 1 1 d . . . . . C11 C 1.2220(7) 0.5821(3) 0.7999(5) 0.0552(13) Uani 1 1 d . . . . . H11 H 1.132344 0.612730 0.741724 0.066 Uiso 1 1 calc R U . . . C12 C 1.3981(8) 0.6065(3) 0.8937(6) 0.0686(16) Uani 1 1 d . . . . . H12 H 1.426222 0.653441 0.898224 0.082 Uiso 1 1 calc R U . . . C13 C 1.5313(7) 0.5623(3) 0.9797(6) 0.0654(15) Uani 1 1 d . . . . . H13 H 1.652549 0.578989 1.039870 0.078 Uiso 1 1 calc R U . . . C14 C 1.4860(7) 0.4932(3) 0.9774(6) 0.0594(14) Uani 1 1 d . . . . . H14 H 1.573843 0.463213 1.038699 0.071 Uiso 1 1 calc R U . . . C15 C 1.3099(6) 0.4681(3) 0.8842(5) 0.0493(12) Uani 1 1 d . . . . . H15 H 1.279576 0.421298 0.883255 0.059 Uiso 1 1 calc R U . . . C16 C 0.7334(6) 0.4853(2) 0.4729(5) 0.0374(10) Uani 1 1 d . . . . . H16 H 0.676756 0.504300 0.377982 0.045 Uiso 1 1 calc R U . . . C17 C 0.9192(6) 0.5135(2) 0.5426(4) 0.0351(10) Uani 1 1 d . . . . . C18 C 1.0509(6) 0.5639(2) 0.4506(5) 0.0398(10) Uani 1 1 d . . . . . C19 C 0.9352(6) 0.6188(2) 0.3553(5) 0.0372(10) Uani 1 1 d . . . . . C20 C 1.0452(7) 0.6474(3) 0.2296(5) 0.0544(13) Uani 1 1 d . . . . . H20 H 1.185055 0.630978 0.203635 0.065 Uiso 1 1 calc R U . . . C21 C 0.9491(9) 0.7003(3) 0.1416(6) 0.0667(15) Uani 1 1 d . . . . . H21 H 1.023022 0.719103 0.055728 0.080 Uiso 1 1 calc R U . . . C22 C 0.7424(8) 0.7251(3) 0.1819(6) 0.0597(14) Uani 1 1 d . . . . . H22 H 0.678019 0.761289 0.124294 0.072 Uiso 1 1 calc R U . . . C23 C 0.6341(7) 0.6969(2) 0.3049(6) 0.0529(13) Uani 1 1 d . . . . . H23 H 0.494585 0.713686 0.330536 0.064 Uiso 1 1 calc R U . . . C24 C 0.7271(6) 0.6434(2) 0.3939(5) 0.0423(11) Uani 1 1 d . . . . . H24 H 0.650722 0.624309 0.478349 0.051 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0661(15) 0.092(2) 0.0774(18) -0.0084(19) -0.0322(13) -0.0150(18) O1 0.0567(17) 0.047(2) 0.0586(19) 0.0167(17) -0.0096(15) -0.0146(18) O2 0.0340(15) 0.061(2) 0.083(2) 0.026(2) 0.0023(14) 0.0018(17) N1 0.0384(17) 0.039(2) 0.045(2) 0.0015(19) -0.0038(16) -0.0039(18) N2 0.0383(17) 0.033(2) 0.0409(19) 0.0023(18) -0.0029(16) -0.0007(18) N3 0.0379(18) 0.038(2) 0.050(2) 0.0003(19) -0.0064(17) -0.0034(19) C1 0.041(2) 0.044(3) 0.045(2) 0.002(2) -0.001(2) 0.002(2) C2 0.038(2) 0.034(3) 0.043(2) -0.007(2) -0.0011(19) 0.003(2) C3 0.052(2) 0.042(3) 0.048(3) 0.007(2) 0.002(2) -0.003(2) C4 0.061(3) 0.059(4) 0.042(3) 0.001(3) -0.013(2) 0.007(3) C5 0.044(2) 0.056(4) 0.054(3) -0.014(3) -0.017(2) 0.004(3) C6 0.045(2) 0.053(3) 0.055(3) 0.001(3) -0.003(2) -0.011(2) C7 0.047(2) 0.044(3) 0.044(2) 0.000(2) -0.004(2) 0.000(2) C8 0.040(2) 0.041(3) 0.042(2) 0.006(2) 0.001(2) 0.001(2) C9 0.0336(19) 0.036(3) 0.043(2) -0.002(2) 0.0009(18) 0.005(2) C10 0.042(2) 0.039(3) 0.043(2) -0.002(2) -0.0012(19) 0.001(2) C11 0.060(3) 0.042(3) 0.063(3) -0.004(3) -0.013(2) 0.002(3) C12 0.077(3) 0.052(4) 0.076(4) -0.007(3) -0.014(3) -0.021(3) C13 0.054(3) 0.074(4) 0.068(3) -0.016(3) -0.014(2) -0.011(3) C14 0.057(3) 0.059(4) 0.061(3) -0.001(3) -0.018(2) 0.005(3) C15 0.052(2) 0.043(3) 0.053(3) -0.001(2) -0.009(2) 0.003(2) C16 0.040(2) 0.030(3) 0.042(2) 0.006(2) 0.0006(18) 0.005(2) C17 0.0325(19) 0.032(3) 0.040(2) 0.004(2) -0.0005(17) 0.002(2) C18 0.038(2) 0.033(3) 0.048(2) 0.000(2) -0.0033(19) -0.002(2) C19 0.033(2) 0.041(3) 0.037(2) 0.003(2) -0.0029(18) -0.004(2) C20 0.049(3) 0.056(4) 0.058(3) 0.012(3) -0.002(2) -0.007(3) C21 0.086(4) 0.062(4) 0.052(3) 0.024(3) -0.006(3) -0.008(3) C22 0.078(4) 0.036(3) 0.063(3) 0.007(3) -0.026(3) 0.001(3) C23 0.049(3) 0.035(3) 0.074(4) -0.003(3) -0.015(2) 0.006(3) C24 0.043(2) 0.034(3) 0.050(3) 0.003(2) 0.001(2) -0.004(2) 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' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 10 11 0.1184 8 10 -1 0.1213 -1 27 -1 0.0685 2 26 -1 0.0804 8 -6 1 0.1189 0 -10 -11 0.1104 0 -14 -10 0.1208 -5 23 1 0.0949 5 -21 2 0.1517 -6 -18 1 0.1349 -6 -13 6 0.1302 1 -23 6 0.0941 -8 5 -2 0.1541 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 C9 N1 C8 122.4(3) . . C16 N2 N3 112.0(3) . . C16 N2 C8 120.7(3) . . N3 N2 C8 126.9(3) . . C1 N3 N2 119.8(3) . . N3 C1 C2 118.7(4) . . N3 C1 H1 120.6 . . C2 C1 H1 120.6 . . C7 C2 C3 119.2(4) . . C7 C2 C1 118.9(4) . . C3 C2 C1 121.9(4) . . C4 C3 C2 120.6(4) . . C4 C3 H3 119.7 . . C2 C3 H3 119.7 . . C5 C4 C3 117.8(4) . . C5 C4 H4 121.1 . . C3 C4 H4 121.1 . . C6 C5 F1 118.1(4) . . C6 C5 C4 123.8(4) . . F1 C5 C4 118.1(4) . . C5 C6 C7 118.1(4) . . C5 C6 H6 120.9 . . C7 C6 H6 120.9 . . C6 C7 C2 120.4(4) . . C6 C7 H7 119.8 . . C2 C7 H7 119.8 . . O1 C8 N1 122.8(4) . . O1 C8 N2 121.3(4) . . N1 C8 N2 115.8(4) . . N1 C9 C17 122.3(4) . . N1 C9 C10 115.3(4) . . C17 C9 C10 122.4(4) . . C11 C10 C15 118.5(4) . . C11 C10 C9 122.5(4) . . C15 C10 C9 118.9(4) . . C12 C11 C10 120.5(4) . . C12 C11 H11 119.8 . . C10 C11 H11 119.8 . . C13 C12 C11 120.5(5) . . C13 C12 H12 119.7 . . C11 C12 H12 119.7 . . C12 C13 C14 119.9(4) . . C12 C13 H13 120.1 . . C14 C13 H13 120.1 . . C13 C14 C15 120.1(4) . . C13 C14 H14 119.9 . . C15 C14 H14 119.9 . . C14 C15 C10 120.4(4) . . C14 C15 H15 119.8 . . C10 C15 H15 119.8 . . N2 C16 C17 122.8(4) . . N2 C16 H16 118.6 . . C17 C16 H16 118.6 . . C16 C17 C9 115.5(4) . . C16 C17 C18 119.2(3) . . C9 C17 C18 124.6(3) . . O2 C18 C17 119.5(4) . . O2 C18 C19 120.3(4) . . C17 C18 C19 120.1(3) . . C20 C19 C24 119.7(4) . . C20 C19 C18 118.1(4) . . C24 C19 C18 122.2(4) . . C19 C20 C21 120.4(4) . . C19 C20 H20 119.8 . . C21 C20 H20 119.8 . . C20 C21 C22 119.6(5) . . C20 C21 H21 120.2 . . C22 C21 H21 120.2 . . C23 C22 C21 120.0(5) . . C23 C22 H22 120.0 . . C21 C22 H22 120.0 . . C22 C23 C24 121.3(4) . . C22 C23 H23 119.4 . . C24 C23 H23 119.4 . . C19 C24 C23 119.1(4) . . C19 C24 H24 120.5 . . C23 C24 H24 120.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 F1 C5 1.361(4) . O1 C8 1.205(5) . O2 C18 1.219(4) . N1 C9 1.306(5) . N1 C8 1.375(5) . N2 C16 1.344(5) . N2 N3 1.408(4) . N2 C8 1.426(5) . N3 C1 1.264(5) . C1 C2 1.469(5) . C1 H1 0.9300 . C2 C7 1.385(5) . C2 C3 1.391(5) . C3 C4 1.376(5) . C3 H3 0.9300 . C4 C5 1.368(6) . C4 H4 0.9300 . C5 C6 1.355(6) . C6 C7 1.383(5) . C6 H6 0.9300 . C7 H7 0.9300 . C9 C17 1.431(5) . C9 C10 1.489(5) . C10 C11 1.383(6) . C10 C15 1.390(5) . C11 C12 1.381(6) . C11 H11 0.9300 . C12 C13 1.364(6) . C12 H12 0.9300 . C13 C14 1.373(7) . C13 H13 0.9300 . C14 C15 1.383(5) . C14 H14 0.9300 . C15 H15 0.9300 . C16 C17 1.358(5) . C16 H16 0.9300 . C17 C18 1.489(5) . C18 C19 1.492(5) . C19 C20 1.375(6) . C19 C24 1.386(5) . C20 C21 1.382(6) . C20 H20 0.9300 . C21 C22 1.383(7) . C21 H21 0.9300 . C22 C23 1.349(7) . C22 H22 0.9300 . C23 C24 1.388(6) . C23 H23 0.9300 . C24 H24 0.9300 . loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag C1 H1 O1 0.93 2.13 2.758(5) 124 . yes C22 H22 F1 0.93 2.50 3.287(6) 143 2_555 yes C7 H7 Cg4 0.93 2.76 3.599(4) 150 2_646 yes C13 H13 Cg4 0.93 2.83 3.674(5) 151 1_656 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C16 N2 N3 C1 -167.5(4) . . . . C8 N2 N3 C1 20.6(5) . . . . N2 N3 C1 C2 179.1(3) . . . . N3 C1 C2 C7 176.9(4) . . . . N3 C1 C2 C3 -3.8(6) . . . . C7 C2 C3 C4 1.6(6) . . . . C1 C2 C3 C4 -177.8(4) . . . . C2 C3 C4 C5 -0.5(6) . . . . C3 C4 C5 C6 -0.7(7) . . . . C3 C4 C5 F1 178.5(4) . . . . F1 C5 C6 C7 -178.4(4) . . . . C4 C5 C6 C7 0.8(7) . . . . C5 C6 C7 C2 0.3(6) . . . . C3 C2 C7 C6 -1.5(6) . . . . C1 C2 C7 C6 177.9(4) . . . . C9 N1 C8 O1 175.6(4) . . . . C9 N1 C8 N2 -6.7(5) . . . . C16 N2 C8 O1 -173.9(4) . . . . N3 N2 C8 O1 -2.5(6) . . . . C16 N2 C8 N1 8.5(5) . . . . N3 N2 C8 N1 179.8(3) . . . . C8 N1 C9 C17 0.3(6) . . . . C8 N1 C9 C10 179.1(4) . . . . N1 C9 C10 C11 -145.1(4) . . . . C17 C9 C10 C11 33.7(6) . . . . N1 C9 C10 C15 33.0(5) . . . . C17 C9 C10 C15 -148.2(4) . . . . C15 C10 C11 C12 2.2(7) . . . . C9 C10 C11 C12 -179.8(4) . . . . C10 C11 C12 C13 0.0(8) . . . . C11 C12 C13 C14 -2.1(8) . . . . C12 C13 C14 C15 2.0(8) . . . . C13 C14 C15 C10 0.2(7) . . . . C11 C10 C15 C14 -2.3(6) . . . . C9 C10 C15 C14 179.6(4) . . . . N3 N2 C16 C17 -176.3(3) . . . . C8 N2 C16 C17 -3.8(6) . . . . N2 C16 C17 C9 -2.8(6) . . . . N2 C16 C17 C18 168.0(3) . . . . N1 C9 C17 C16 4.7(6) . . . . C10 C9 C17 C16 -174.0(4) . . . . N1 C9 C17 C18 -165.5(4) . . . . C10 C9 C17 C18 15.8(6) . . . . C16 C17 C18 O2 -134.2(4) . . . . C9 C17 C18 O2 35.6(6) . . . . C16 C17 C18 C19 43.6(5) . . . . C9 C17 C18 C19 -146.6(4) . . . . O2 C18 C19 C20 21.3(6) . . . . C17 C18 C19 C20 -156.5(4) . . . . O2 C18 C19 C24 -155.8(4) . . . . C17 C18 C19 C24 26.4(6) . . . . C24 C19 C20 C21 -0.2(7) . . . . C18 C19 C20 C21 -177.4(4) . . . . C19 C20 C21 C22 0.9(7) . . . . C20 C21 C22 C23 -1.1(7) . . . . C21 C22 C23 C24 0.6(7) . . . . C20 C19 C24 C23 -0.3(6) . . . . C18 C19 C24 C23 176.8(4) . . . . C22 C23 C24 C19 0.1(6) . . . . loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0.2829 10.1473 10.9151 -0.0174 -0.0720 0.9973 7.8303 10.4110 -0.5804 0.5093 0.8317 0.2210 -1.0030 27.2243 -0.5627 -0.6796 0.6445 0.3505 2.2761 26.3313 -1.1457 -0.3604 0.8693 0.3382 8.1820 -5.7829 1.3621 0.9156 0.3795 0.1330 -0.0194 -10.4706 -10.8771 0.0497 0.0809 -0.9955 -0.0872 -13.7364 -10.1837 0.1233 -0.0297 -0.9919 -4.8100 22.5661 0.6336 -0.9214 0.2210 0.3196 5.2091 -21.1906 1.6548 0.9658 -0.2316 -0.1170 -6.4893 -17.5308 1.0741 -0.2244 -0.9361 -0.2709 -6.2445 -12.5053 6.1320 -0.2286 -0.9532 0.1977 0.5777 -23.3307 6.1290 0.6441 -0.7537 0.1309 -8.1714 5.4763 -1.6261 -0.9122 -0.3781 -0.1578