#------------------------------------------------------------------------------ #$Date: 2019-10-07 12:15:10 +0300 (Mon, 07 Oct 2019) $ #$Revision: 219128 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/44/7234418.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_7234418 loop_ _publ_author_name 'Guo-Ping Yong' 'Chen Shen' 'Cong Zhang' 'Yu-Mei Zhao' _publ_section_title ; Morphology-controllable fabrication of organic microcrystals by solid-phase reactions: revealing morphology-sensitive highly efficient phosphorescence and enhanced near-infrared absorption ; _journal_name_full 'Journal of Materials Chemistry C' _journal_page_first 9048 _journal_page_last 9052 _journal_paper_doi 10.1039/C5TC01770J _journal_volume 3 _journal_year 2015 _chemical_formula_sum 'C14 H9 B F2 N4 O' _chemical_formula_weight 298.06 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 105.03(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.213(2) _cell_length_b 9.1955(18) _cell_length_c 13.667(3) _cell_measurement_temperature 293(2) _cell_volume 1239.6(5) _computing_cell_refinement 'CrysAlisPro (Agilent Technologies)' _computing_data_collection 'CrysAlisPro (Agilent Technologies)' _computing_data_reduction 'CrysAlisPro (Agilent Technologies)' _computing_molecular_graphics 'Ortep-3 (L. J. Farrugia, 2001)' _computing_publication_material SHELXL-2014 _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.959 _diffrn_measurement_device_type 'Gemini S Ultra, Agilent Technologies' _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0411 _diffrn_reflns_av_unetI/netI 0.0428 _diffrn_reflns_Laue_measured_fraction_full 0.987 _diffrn_reflns_Laue_measured_fraction_max 0.959 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 4288 _diffrn_reflns_point_group_measured_fraction_full 0.987 _diffrn_reflns_point_group_measured_fraction_max 0.959 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 25.644 _diffrn_reflns_theta_min 2.234 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_T_max 0.974 _exptl_absorpt_correction_T_min 0.965 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour pale-yellow _exptl_crystal_density_diffrn 1.597 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 608 _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.240 _exptl_crystal_size_min 0.210 _refine_diff_density_max 0.349 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.067 _refine_ls_extinction_coef 0.013(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 200 _refine_ls_number_reflns 2252 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.0965 _refine_ls_R_factor_gt 0.0749 _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^)+(0.1506P)^2^+0.1851P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2081 _refine_ls_wR_factor_ref 0.2461 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1546 _reflns_number_total 2252 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file J-Mater-Chem-C-2015-3-9048.cif _cod_data_source_block 1 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7234418 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.972 _shelx_estimated_absorpt_t_max 0.981 _shelx_res_file ; sc141010.res created by SHELXL-2014/7 TITL SC141010 in P2(1)/n CELL 0.71073 10.2131 9.1955 13.6673 90.000 105.033 90.000 ZERR 3.00 0.0020 0.0018 0.0027 0.000 0.030 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H B N O F UNIT 42 27 3 12 3 6 MERG 2 FMAP 2 PLAN 25 L.S. 20 acta 50 bond $H conf size 0.30 0.24 0.21 WGHT 0.150600 0.185100 EXTI 0.012749 FVAR 6.79795 C1 1 0.248360 0.023754 0.537381 11.00000 0.05084 0.07922 = 0.06713 0.00037 0.01869 -0.00633 C2 1 0.169755 0.122540 0.573719 11.00000 0.05990 0.08965 = 0.07410 -0.00216 0.02189 -0.00034 AFIX 43 H2A 2 0.186414 0.141359 0.642716 11.00000 -1.20000 AFIX 0 C3 1 0.066931 0.191561 0.505110 11.00000 0.06293 0.08752 = 0.09827 -0.00177 0.02755 0.00932 AFIX 43 H3A 2 0.012003 0.257129 0.527820 11.00000 -1.20000 AFIX 0 C4 1 0.043391 0.164561 0.400864 11.00000 0.06225 0.09116 = 0.08920 0.01124 0.01419 0.00810 AFIX 43 H4A 2 -0.026169 0.212998 0.355009 11.00000 -1.20000 AFIX 0 C5 1 0.121594 0.068348 0.367028 11.00000 0.05827 0.08979 = 0.07058 0.00716 0.01203 0.00248 AFIX 43 H5A 2 0.106089 0.049761 0.298078 11.00000 -1.20000 AFIX 0 C6 1 0.316702 -0.102496 0.419270 11.00000 0.05459 0.08246 = 0.05764 0.00013 0.01160 0.00100 AFIX 43 H6A 2 0.322572 -0.138817 0.357043 11.00000 -1.20000 AFIX 0 C7 1 0.397717 -0.138305 0.512363 11.00000 0.05537 0.07702 = 0.05843 0.00123 0.01366 -0.00485 C8 1 0.510173 -0.229757 0.552861 11.00000 0.05088 0.07935 = 0.06093 0.00273 0.01287 -0.00283 C9 1 0.564600 -0.360316 0.407142 11.00000 0.05916 0.09296 = 0.05970 0.00194 0.01291 -0.00101 AFIX 43 H9A 2 0.499313 -0.314155 0.356467 11.00000 -1.20000 AFIX 0 C10 1 0.647112 -0.461524 0.383490 11.00000 0.06168 0.09601 = 0.06854 -0.00742 0.01752 -0.00090 AFIX 43 H10A 2 0.637038 -0.486644 0.316027 11.00000 -1.20000 AFIX 0 C11 1 0.747768 -0.529264 0.459240 11.00000 0.06133 0.08857 = 0.08800 -0.00487 0.02111 0.00660 AFIX 43 H11A 2 0.804477 -0.597861 0.441507 11.00000 -1.20000 AFIX 0 C12 1 0.763127 -0.495591 0.558159 11.00000 0.05727 0.09228 = 0.07731 0.00214 0.01188 0.00781 AFIX 43 H12A 2 0.829865 -0.541080 0.608157 11.00000 -1.20000 AFIX 0 C13 1 0.678367 -0.392496 0.584412 11.00000 0.05402 0.08312 = 0.05941 0.00411 0.00772 -0.00351 C14 1 0.570732 -0.242338 0.654595 11.00000 0.05664 0.09157 = 0.05866 0.00259 0.01463 -0.00171 B1 3 0.407964 -0.084492 0.702269 11.00000 0.07295 0.09262 = 0.05907 -0.00387 0.01902 0.00141 F1 6 0.425086 0.042575 0.752245 11.00000 0.16083 0.12492 = 0.08397 -0.03072 -0.01853 0.04112 F2 6 0.310261 -0.167545 0.730688 11.00000 0.08316 0.19702 = 0.09690 0.05223 0.04024 0.01376 N1 4 0.224135 -0.001526 0.435724 11.00000 0.05026 0.07786 = 0.06323 0.00531 0.01212 -0.00216 N2 4 0.355507 -0.059472 0.585966 11.00000 0.05384 0.08066 = 0.06099 0.00011 0.01689 -0.00061 N3 4 0.578526 -0.326729 0.506802 11.00000 0.04988 0.07722 = 0.06101 0.00255 0.01348 -0.00191 N4 4 0.673198 -0.340255 0.675646 11.00000 0.05704 0.09495 = 0.06217 0.00406 0.00911 0.00610 O1 5 0.534363 -0.166517 0.726918 11.00000 0.06863 0.11525 = 0.05485 -0.00409 0.00904 0.00980 HKLF 4 REM SC141010 in P2(1)/n REM R1 = 0.0749 for 1546 Fo > 4sig(Fo) and 0.0965 for all 2252 data REM 200 parameters refined using 0 restraints END WGHT 0.1507 0.1854 REM Highest difference peak 0.349, deepest hole -0.413, 1-sigma level 0.067 Q1 1 0.5039 0.0549 0.7179 11.00000 0.05 0.35 Q2 1 0.2374 0.2689 0.6394 11.00000 0.05 0.21 Q3 1 0.4717 -0.2461 0.4397 11.00000 0.05 0.21 Q4 1 0.3767 0.1226 0.5852 11.00000 0.05 0.21 Q5 1 0.3437 -0.0763 0.7582 11.00000 0.05 0.19 Q6 1 0.6883 -0.1829 0.7610 11.00000 0.05 0.18 Q7 1 0.6260 -0.5982 0.4310 11.00000 0.05 0.18 Q8 1 0.5450 -0.6327 0.2958 11.00000 0.05 0.18 Q9 1 0.2086 -0.3018 0.7329 11.00000 0.05 0.17 Q10 1 0.0128 -0.1297 0.2757 11.00000 0.05 0.17 Q11 1 0.5219 0.1260 0.7924 11.00000 0.05 0.17 Q12 1 0.5284 -0.5249 0.3791 11.00000 0.05 0.16 Q13 1 0.3187 -0.0572 0.7391 11.00000 0.05 0.16 Q14 1 0.8728 -0.5418 0.6319 11.00000 0.05 0.16 Q15 1 0.0255 0.2070 0.6406 11.00000 0.05 0.16 Q16 1 0.4375 0.0507 0.6470 11.00000 0.05 0.16 Q17 1 0.5935 -0.5948 0.3399 11.00000 0.05 0.16 Q18 1 0.4880 -0.5180 0.2950 11.00000 0.05 0.16 Q19 1 0.3829 0.0361 0.6654 11.00000 0.05 0.16 Q20 1 0.4387 -0.2738 0.3473 11.00000 0.05 0.16 Q21 1 0.1001 -0.0925 0.3794 11.00000 0.05 0.15 Q22 1 0.5247 -0.4057 0.6405 11.00000 0.05 0.15 Q23 1 0.0764 -0.0540 0.3011 11.00000 0.05 0.15 Q24 1 0.1198 -0.1625 0.3196 11.00000 0.05 0.15 Q25 1 0.1757 0.2819 0.5655 11.00000 0.05 0.14 ; _shelx_res_checksum 31774 _shelx_hkl_file ; 0 0 -1 18.3668 10.5796 1 0 0 -2 257675. 1450.43 1 0 0 -3 12.9759 26.7111 1 0 0 -4 55608.1 1024.67 1 0 0 -5-35.4625 49.5012 1 0 0 5 11.2640 29.0369 11 0 0 6 166618. 1504.30 11 0 0 7 57.9960 36.0959 11 0 0 8 276.356 82.4042 11 0 0 9-29.0444 54.4925 2 0 0 9-41.1539 61.4743 11 0 0 10 304.647 164.653 2 0 0 10 224.955 91.0250 9 0 0 10 273.428 93.0543 11 0 0 11-32.9553 66.1687 9 0 0 11 55.9413 69.1454 11 0 0 12 8413.96 575.013 6 0 0 12 8266.10 518.592 9 0 0 13-61.2202 79.4895 6 0 0 13-45.9471 70.2954 9 0 0 14 1126.39 195.395 6 0 0 14 1108.31 183.546 9 0 0 15 3.97254 47.0443 6 0 0 15-43.3710 38.6959 9 0 -1 0 11.6180 7.54513 1 0 -1 1 72570.3 503.501 2 0 -1 -1 75305.3 605.817 1 0 -1 -2 173014. 1263.38 1 0 -1 -3 64.7035 40.7108 1 0 -1 -4 49887.8 983.818 1 0 -1 -5 325.948 97.9197 1 0 1 5 410.760 67.5989 11 0 1 6 40670.8 726.879 11 0 -1 6 39803.6 747.964 11 0 -1 -6 38978.6 1107.76 1 0 1 7 20974.1 582.684 11 0 -1 7 20620.3 869.587 2 0 -1 7 21448.1 609.565 11 0 1 8-3.46602 31.6102 11 0 -1 8 33.4616 59.5234 2 0 -1 8-15.7010 41.0565 11 0 -1 9 725.985 210.539 2 0 1 9 703.940 127.014 11 0 1 9 665.352 205.797 2 0 -1 9 840.120 152.357 11 0 -1 10 4327.33 347.765 11 0 1 10 4326.14 333.448 11 0 -1 10 3492.32 461.773 2 0 1 10 4067.64 340.132 9 0 -1 10 3833.01 320.703 9 0 1 11 820.142 161.949 11 0 -1 11 989.146 171.668 9 0 -1 11 870.384 171.641 11 0 1 11 761.049 168.669 9 0 1 12 511.803 140.677 6 0 -1 12 594.559 157.762 6 0 -1 12 710.873 154.586 9 0 1 12 477.318 132.549 9 0 1 13 1742.97 253.827 6 0 -1 13 1675.73 222.888 9 0 -1 13 1664.01 253.333 6 0 1 13 1890.61 252.919 9 0 -1 14 794.909 147.294 9 0 1 14 743.900 148.821 9 0 1 14 769.754 136.659 6 0 -1 14 659.657 153.026 6 0 1 15 315.488 86.7657 9 0 -1 15 330.907 95.7539 6 0 1 15 404.923 101.143 6 0 -2 0 79569.0 591.350 1 0 -2 -1 57156.6 625.043 1 0 -2 1 53075.9 565.367 1 0 -2 -2 24094.7 517.141 1 0 -2 2 21263.7 382.353 2 0 -2 3 21302.5 502.243 2 0 -2 -3 21214.5 592.232 1 0 -2 4 9730.21 392.395 2 0 -2 -4 9187.66 458.165 1 0 2 5 381.074 64.6850 11 0 -2 5 422.627 99.3835 2 0 -2 5 349.626 66.9870 11 0 -2 -5 248.013 96.2356 1 0 -2 6 93228.1 1168.53 11 0 2 6 93741.2 1098.79 11 0 -2 6 96031.7 1636.88 2 0 -2 -6 91385.7 1721.56 1 0 2 7 29443.0 679.133 11 0 -2 7 29243.4 722.719 11 0 -2 -7 30116.6 1089.13 1 0 -2 7 31786.1 1057.85 2 0 2 8 5689.59 322.086 11 0 -2 8 6086.18 513.308 2 0 -2 8 5917.61 361.120 11 0 2 9 1194.36 286.120 2 0 -2 9 1040.18 164.403 11 0 2 9 1020.02 152.047 11 0 2 10 2756.31 266.937 11 0 -2 10 2613.05 271.975 11 0 2 10 2621.84 275.177 9 0 -2 11 7955.91 499.168 11 0 2 11 7833.21 505.737 9 0 2 12 597.696 146.803 9 0 -2 12 757.659 180.327 6 0 2 12 654.990 163.002 6 0 2 13 553.101 148.181 9 0 -2 13 683.959 168.056 6 0 2 13 584.611 136.997 6 0 -2 -13 676.502 156.017 16 0 2 14 229.600 103.615 9 0 2 14 208.567 83.5224 6 0 -2 14 96.6975 64.2994 6 0 -2 15 61.3245 52.8890 6 0 2 15 30.6925 48.8218 9 0 -3 0 32.3326 18.6915 1 0 -3 -1 7445.27 269.769 1 0 -3 -1 8786.19 268.293 10 0 -3 -2 3596.05 226.004 1 0 -3 -2 3971.45 194.024 10 0 -3 2 3341.87 184.719 1 0 -3 -3 207.288 56.1746 10 0 -3 -3 108.102 53.0929 1 0 -3 4 1454.55 120.785 11 0 -3 -4 1681.86 203.187 1 0 -3 -5 4046.00 341.895 1 0 -3 5 3881.86 218.762 11 0 -3 6 63.1731 38.3631 11 0 -3 -6-54.3839 61.7440 1 0 -3 7 6098.79 336.937 11 0 -3 8 465.599 103.902 11 0 -3 -8 693.218 116.618 10 0 -3 9 12208.0 551.220 11 0 3 9 12435.1 582.120 9 0 3 10 234.390 102.199 9 0 -3 10 237.134 93.0031 6 0 -3 10 200.457 84.3400 11 0 -3 11 8682.95 573.336 6 0 -3 11 7961.82 486.941 11 0 3 11 8477.45 529.869 9 0 3 12 1050.92 194.931 9 0 -3 12 1139.60 220.780 6 0 3 13 393.166 119.022 9 0 -3 13 380.443 126.742 6 0 -3 -13 466.500 129.560 16 0 -3 14 4.36985 60.9263 6 0 3 14-6.54390 49.8062 9 0 -3 -14 107.521 56.4505 16 0 3 15 12.0940 45.4137 9 0 -4 0 3342.50 197.963 10 0 -4 1 16804.4 434.034 10 0 -4 -1 17270.7 464.733 10 0 -4 2 7009.70 275.154 10 0 -4 -2 6910.94 300.519 10 0 -4 -3 11457.5 469.083 1 0 -4 -3 12098.2 414.518 10 0 -4 3 12010.9 375.146 10 0 -4 -4 776.599 113.692 10 0 -4 -4 873.495 147.315 1 0 -4 -5 77168.8 1158.68 10 0 -4 -5 77651.0 1497.66 1 0 -4 -6 1339.43 219.298 1 0 -4 -6 1481.74 171.110 10 0 -4 -7 4035.89 291.510 10 0 -4 7 3719.19 262.531 11 0 -4 -8 3332.33 271.060 10 0 -4 -8 2990.83 263.651 14 0 -4 8 2505.06 232.834 11 0 4 9 1186.93 184.476 9 0 -4 9 1507.18 192.970 11 0 -4 10 17804.0 761.997 6 0 -4 10 17918.5 696.218 11 0 4 10 19526.8 771.342 9 0 4 11 1855.01 242.148 9 0 -4 11 1485.79 233.678 6 0 -4 12 4232.15 373.229 6 0 4 12 4704.64 383.601 9 0 4 13 81.4696 59.2976 9 0 -4 -13 48.5489 71.0533 16 0 -4 13-12.2982 60.9943 6 0 -4 -14 273.969 95.7166 16 0 4 14 145.373 62.6708 9 0 -5 0 44.3487 44.1998 10 0 -5 1 340.439 79.2738 10 0 -5 -1 398.920 90.4583 10 0 -5 2 4058.26 249.527 10 0 -5 -2 4466.19 287.184 10 0 -5 3 883.543 120.911 10 0 -5 -3 1096.91 150.818 10 0 -5 -4 9717.51 446.884 10 0 -5 -5-26.0390 55.8389 10 0 -5 -6 1464.33 188.047 10 0 -5 -7 531.928 152.602 15 0 -5 -7 984.484 156.376 14 0 -5 -7 770.672 147.181 10 0 -5 -8 176.952 84.8161 10 0 -5 -8 33.1986 63.3748 14 0 -5 -9 79.8400 54.9367 10 0 -5 -9 157.125 135.406 15 0 5 10 3534.29 317.702 9 0 5 11 375.994 105.862 9 0 5 12 879.295 151.190 9 0 -5 -12 1050.38 195.081 16 0 -5 -13 89.2168 69.7934 16 0 5 13-49.3540 47.0895 9 0 5 14 160.942 52.9279 9 0 -5 -14 27.6255 39.6340 16 0 -6 0 24843.2 722.583 10 0 -6 -1 1875.71 208.850 10 0 -6 1 1988.36 205.230 10 0 -6 -2 3398.16 284.930 10 0 -6 2 3020.90 249.002 10 0 -6 3 13172.4 520.993 10 0 -6 -3 14761.5 609.001 10 0 -6 -4 19686.8 726.303 10 0 -6 -5 5128.25 377.294 10 0 -6 -5 3589.26 396.783 15 0 -6 -6 430.430 156.359 15 0 -6 -6 276.208 91.0764 14 0 -6 -6 274.849 113.300 10 0 -6 -7 609.200 136.075 14 0 -6 -7 624.399 183.514 15 0 -6 -7 726.202 149.878 10 0 -6 -8 383.582 112.935 10 0 -6 -8 366.005 139.640 15 0 -6 -8 364.282 110.087 14 0 -6 -9 5653.07 508.888 15 0 -6 -9 5149.30 369.137 10 0 -6 -10 72.6002 82.8631 16 0 -6 -10-54.9214 111.332 15 0 -6 -11 551.170 149.191 16 0 -6 -12 138.217 80.8830 16 0 -6 -13 532.072 116.464 16 0 -7 0-60.3722 75.6625 10 0 -7 1 1665.08 211.213 10 0 -7 -1 1461.66 252.443 15 0 -7 -1 1874.61 234.978 10 0 -7 -2 296.143 107.115 10 0 -7 -2 189.325 94.3286 15 0 -7 2 168.079 89.2034 10 0 -7 -3 2593.81 287.990 10 0 -7 -3 1705.21 278.061 15 0 -7 -4-29.8648 66.6732 10 0 -7 -4-92.8675 106.790 15 0 -7 -5 17.2899 83.6967 10 0 -7 -5-62.0251 105.725 15 0 -7 -6 790.928 151.512 14 0 -7 -6 1015.96 191.165 10 0 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699.001 146.807 9 2 1 12 3.36277 63.2002 9 2 1 13 19.9845 52.8087 9 2 1 13-78.1267 82.8993 6 2 -1 13-77.9301 71.6049 6 2 1 14 330.392 100.073 9 2 1 14 223.330 86.7642 6 2 -1 14 118.015 55.0137 6 2 -1 15-12.3639 29.0423 6 -2 2 16-51.1467 51.6675 9 -2 2 15 1331.71 176.709 9 -2 2 14 26.3549 55.6501 9 -2 -2 14-4.90563 60.4349 6 -2 2 13 1922.46 250.739 6 2 -2 -13 2059.03 251.701 16 -2 -2 13 1397.52 203.588 11 -2 -2 13 2276.28 299.839 6 -2 2 13 2085.82 268.745 9 -2 -2 13 1987.72 242.378 9 -2 -2 12 124.125 88.0947 6 -2 2 12 164.237 84.7218 9 -2 -2 12 255.765 114.481 11 2 -2 -12 199.356 80.9530 16 -2 2 12 97.0684 63.6773 6 -2 -2 12 58.9647 63.8703 9 -2 -2 11 11156.9 586.074 11 -2 2 11 9844.41 557.612 6 -2 -2 11 10830.3 637.039 6 -2 2 11 10696.0 524.080 11 -2 -2 11 10251.8 546.028 9 -2 2 11 11583.3 603.642 9 -2 -2 10 5946.53 598.283 2 -2 -2 10 6222.81 419.612 11 -2 2 10 5958.15 376.856 11 -2 -2 10 5665.01 438.969 6 -2 2 10 5801.69 400.282 9 2 -2 -10 6267.79 444.688 16 -2 -2 9 278.397 130.646 2 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593.590 133.108 9 2 2 13 514.888 119.114 6 2 -2 13 608.011 136.234 6 2 2 14 341.255 84.4373 9 2 2 14 278.410 81.3967 6 2 -2 14 240.492 70.6539 6 -2 3 15-33.9211 53.8116 9 -2 3 14 849.752 155.896 9 2 -3 -14 901.582 163.791 16 -2 3 13 222.005 90.0943 9 2 -3 -13 293.339 103.590 16 -2 -3 13 425.520 122.507 6 -2 3 12 586.441 147.490 9 -2 -3 12 311.918 94.2070 11 -2 -3 12 613.847 159.643 6 2 -3 -12 686.802 173.679 16 -2 -3 11 4191.30 390.554 6 -2 -3 11 4373.07 361.109 11 -2 3 11 4268.34 367.806 9 2 -3 -11 4789.59 424.944 16 2 -3 -11 3979.73 431.395 15 -2 -3 10 319.386 103.928 11 2 -3 -10 278.724 99.4250 16 2 -3 -10 416.564 147.660 15 -2 -3 10 429.288 141.717 6 -2 3 10 364.594 110.042 9 -2 -3 9 1167.86 183.565 11 -2 3 9 986.840 226.076 2 -2 3 8 5933.23 551.526 2 -2 -3 7 12345.7 698.955 2 -2 3 7 12545.4 742.292 2 -2 -3 6 956.597 128.168 4 -2 3 6 728.906 160.619 2 2 -3 -6 843.890 104.677 10 -2 -3 6 726.086 160.348 2 -2 3 5 20416.8 778.429 2 2 -3 -5 18595.3 462.249 10 2 -3 -4 21620.6 482.699 10 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361.704 16 -2 4 12 3003.15 304.949 9 2 -4 -11 45.9565 89.9969 15 -2 4 11-55.2220 95.2740 9 -2 -4 11-91.6604 100.317 11 -2 -4 11 17.8408 53.4156 6 2 -4 -11 118.974 91.0088 16 2 -4 -10 1666.92 291.997 15 -2 -4 10 1558.95 213.606 11 -2 -4 10 1481.07 220.553 6 2 -4 -10 1589.03 262.074 16 -2 4 10 1332.81 199.363 9 -2 -4 9 78.0498 47.4231 11 2 -4 -9 135.325 93.9310 16 2 -4 -9-71.2181 147.513 15 -2 -4 8 2339.27 236.279 11 2 -4 -7 8.89913 48.0930 10 2 -4 -6 56.5189 51.9668 10 2 -4 -5 22758.3 592.781 10 -2 -4 4 26460.3 922.124 1 2 -4 -4 23691.5 588.840 10 -2 -4 3 9839.39 463.372 1 2 -4 -3 10873.1 388.601 10 2 -4 -2 55062.7 863.628 10 -2 -4 2 56870.0 1116.63 1 2 -4 -1 9964.02 365.256 10 -2 -4 1 9902.09 453.171 1 -2 -4 1 9306.96 323.913 10 -2 -4 0 6632.48 293.760 10 2 -4 0 6891.47 308.599 10 -2 -4 0 7648.84 426.292 1 -2 -4 -1 18882.3 528.282 10 -2 -4 -1 19594.2 696.588 1 2 -4 1 18057.4 516.783 10 -2 -4 -2 2737.80 272.010 1 2 -4 2 2428.68 201.609 10 -2 -4 -3 36124.2 1064.24 1 -2 -4 -4 224.111 97.9381 1 -2 -4 -5 32881.9 1166.64 1 -2 -4 -6 753.015 197.475 1 -2 -4 -7 17791.0 640.641 14 -2 -4 -7 17287.7 941.431 1 -2 -4 -8 442.241 111.283 14 -2 -4 -8 447.293 125.825 5 -2 -4 -9-82.9599 83.9664 5 -2 -4 -9-43.0007 58.8384 14 -2 -4 -9 109.757 53.8330 10 -2 -4 -10 4712.25 407.158 5 2 4 10 4139.52 365.244 9 2 -4 11 1400.08 209.557 6 2 4 11 1980.77 251.928 9 2 -4 12 457.364 116.074 6 2 4 12 408.207 121.339 9 -2 -4 -13 60.7837 56.3916 16 2 -4 13 106.152 62.9303 6 2 4 13-73.9828 70.4839 9 2 4 14 19.8534 38.7927 9 2 -5 -14-93.2680 57.8040 16 2 -5 -13 51.5441 61.1956 16 2 -5 -12 40.4529 70.2761 16 2 -5 -11 975.024 225.325 15 2 -5 -11 1010.33 209.581 16 2 -5 -10 220.845 132.073 15 2 -5 -10 514.751 146.392 16 2 -5 -9-33.2008 81.5968 16 2 -5 -9-118.371 150.510 15 2 -5 -8 588.089 164.203 16 2 -5 -8 469.537 158.971 15 2 -5 -7 56.2153 54.0552 10 2 -5 -7-3.05276 96.5380 15 2 -5 -6 75.4509 56.2525 10 2 -5 -5 6248.52 358.828 10 2 -5 -4 5137.93 319.756 10 2 -5 -3 23.3150 61.5191 10 -2 -5 2 4130.13 243.798 10 2 -5 -2 4038.61 273.204 10 -2 -5 1 2793.10 215.441 10 2 -5 -1 2751.54 226.103 10 2 -5 0 63.3590 55.2247 10 -2 -5 0-37.4566 45.2212 10 -2 -5 -1 1057.84 137.872 10 2 -5 1 932.237 140.995 10 -2 -5 -2 182.231 69.7704 10 2 -5 2 98.9864 63.8264 10 -2 -5 -3-24.4077 68.6177 10 -2 -5 -4 748.102 137.989 10 -2 -5 -5 111.587 70.4463 10 -2 -5 -6 449.373 110.102 14 -2 -5 -6 438.420 144.438 15 -2 -5 -6 402.859 120.231 10 -2 -5 -7 31.3047 56.1149 14 -2 -5 -7-2.32720 54.7603 10 -2 -5 -8 7769.84 477.473 10 -2 -5 -8 6680.93 453.147 5 -2 -5 -8 8027.71 464.199 14 -2 -5 -9 630.067 150.457 5 -2 -5 -9 900.792 161.858 14 2 5 9 549.375 135.686 9 -2 -5 -9 995.380 173.557 10 2 5 10 2619.80 282.713 9 2 5 11 303.678 95.6689 9 2 5 12-66.3280 48.6303 9 2 5 13 70.0305 45.9827 9 -2 -5 -13 55.8546 44.2806 16 2 -6 -14-38.0863 45.5743 16 2 -6 -13 864.372 154.705 16 2 -6 -12 1249.15 197.354 16 2 -6 -11 513.375 151.703 16 2 -6 -11 424.399 145.644 15 2 -6 -10 9012.17 613.568 16 2 -6 -10 10369.2 728.855 15 2 -6 -9 5318.45 457.517 16 2 -6 -9 4685.67 489.036 15 2 -6 -8 5958.29 498.579 16 2 -6 -8 6682.38 570.800 15 2 -6 -7 10380.8 520.236 10 2 -6 -7 10018.4 601.774 16 2 -6 -7 11670.8 749.238 15 2 -6 -6 139.112 117.258 15 2 -6 -6 54.4785 53.3346 13 2 -6 -6-7.52524 70.2886 10 2 -6 -6-96.5075 87.9725 16 2 -6 -5 285.729 127.384 15 2 -6 -5 640.446 138.925 10 2 -6 -4 6649.23 408.070 10 2 -6 -3 360.313 100.887 10 2 -6 -2 218.283 91.3268 10 -2 -6 1 4747.94 310.724 10 2 -6 -1 5322.97 359.859 10 2 -6 0 3028.32 277.752 10 -2 -6 0 2987.17 261.608 10 -2 -6 -1 487.444 115.249 10 2 -6 1 592.397 142.899 10 -2 -6 -2 54.8950 57.5715 10 2 -6 2-13.3059 89.3149 10 -2 -6 -3 700.690 142.038 10 -2 -6 -4 3490.68 285.089 14 -2 -6 -4 3527.88 320.347 10 -2 -6 -4 3328.60 354.532 15 -2 -6 -5-31.4801 57.1152 10 -2 -6 -5 47.3109 42.2274 14 -2 -6 -5-45.2490 84.0043 15 -2 -6 -6 529.962 158.589 15 -2 -6 -6 422.480 111.380 14 -2 -6 -6 559.901 130.937 10 -2 -6 -7 1870.06 231.233 14 -2 -6 -7 1497.08 220.061 10 -2 -6 -7 1185.64 229.481 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-2 9 79.9456 47.3291 9 -11 -2 8 183.418 67.3896 9 -11 -2 7-75.1504 74.2358 9 -11 -2 6 395.750 115.517 9 -11 -2 5 212.895 84.1180 7 -11 -2 5 151.903 88.7897 9 -11 -2 4 490.766 114.494 7 -11 -2 4 308.697 89.6136 9 -11 -2 3 625.925 124.692 7 -11 -2 3 767.130 144.076 9 -11 -2 2 83.5694 66.4959 7 -11 -2 2 36.5464 76.7074 9 -11 -2 1 208.738 74.8949 7 -11 2 0 63.0161 49.4527 8 -11 -2 0 74.1510 57.6825 8 -11 2 -1 456.638 99.7060 8 -11 -2 -1 351.734 82.6391 8 -11 -2 -2 252.875 76.7131 5 -11 -2 -2 354.539 75.8679 8 -11 -3 9 33.5472 37.6876 9 -11 -3 8 26.7629 43.8993 9 -11 -3 7 693.190 132.955 9 -11 -3 6 216.277 73.3626 7 -11 -3 6 163.161 78.2606 9 -11 -3 5 463.591 108.275 7 -11 -3 5 574.864 122.705 9 -11 -3 4 220.054 71.6983 7 -11 -3 4 203.987 87.6243 9 -11 -3 3 78.0351 56.1261 7 -11 -3 3 64.0759 47.1727 9 -11 -3 2 98.7121 54.3254 7 -11 -3 1 19.3850 39.5035 8 -11 -3 1 87.8998 45.7156 7 -11 -3 0 5.68976 34.1667 8 -11 -3 0 131.764 58.4276 7 -11 -3 -2 27.6409 33.8181 5 -11 -4 8 10.4266 44.9043 7 -11 -4 7 21.3263 40.4793 7 -11 -4 7-35.6647 54.0760 9 -11 -4 6 73.6696 42.5921 7 -11 -4 6 43.9312 41.8345 9 -11 -4 5 142.976 64.0049 7 -11 -4 5 177.385 73.7233 9 -11 -4 4 296.316 77.8359 7 -11 -4 3 77.6700 52.7265 7 -11 -4 2 138.537 65.6579 7 -11 -4 1 47.2937 36.0404 7 -11 -5 4 6.34496 34.1526 7 -11 -5 3 916.974 107.207 7 -12 0 7-51.6575 37.5403 9 -12 0 6 296.877 70.7449 9 -12 0 5-56.5500 38.0016 9 -12 0 1-19.4432 43.4268 8 -12 0 0 1230.30 129.902 8 -12 -1 7-20.3841 44.2425 9 -12 -1 6 65.1508 38.8756 7 -12 -1 6 130.210 35.8423 9 -12 -1 5 213.092 72.2090 9 -12 1 1 398.487 80.6592 8 -12 -1 1 397.561 81.5663 8 -12 -2 7 126.878 55.6987 9 -12 -2 6 379.635 73.9048 7 -12 -2 6 190.644 64.7081 9 -12 -2 5 26.6362 42.2086 7 -12 -2 5 15.1080 32.1844 9 -12 -2 4 997.864 111.224 7 -12 -2 3 674.569 95.1499 7 0 0 0 0.00 0.00 0 TITL SC141010 in P2(1)/n REM P2(1)/n (#14 in standard setting) CELL 1.54184 10.213118 9.195463 13.667284 90.0000 105.0326 90.0000 ZERR 2.00 0.001169 0.001284 0.001210 0.0000 0.0105 0.0000 LATT 1 SYMM -x+1/2, y+1/2,-z+1/2 SFAC C H B N O F Cl UNIT 40.00 40.00 2.00 4.00 4.00 6.00 2.00 TREF HKLF 4 END ; _shelx_hkl_checksum 7473 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 C1 C 0.2484(3) 0.0238(4) 0.5374(2) 0.0651(8) Uani 1 1 d . . . . . C2 C 0.1698(3) 0.1225(4) 0.5737(3) 0.0737(10) Uani 1 1 d . . . . . H2A H 0.1864 0.1414 0.6427 0.088 Uiso 1 1 calc R U . . . C3 C 0.0669(4) 0.1916(4) 0.5051(3) 0.0817(10) Uani 1 1 d . . . . . H3A H 0.0120 0.2571 0.5278 0.098 Uiso 1 1 calc R U . . . C4 C 0.0434(4) 0.1646(4) 0.4009(3) 0.0819(11) Uani 1 1 d . . . . . H4A H -0.0262 0.2130 0.3550 0.098 Uiso 1 1 calc R U . . . C5 C 0.1216(3) 0.0683(4) 0.3670(3) 0.0738(10) Uani 1 1 d . . . . . H5A H 0.1061 0.0498 0.2981 0.089 Uiso 1 1 calc R U . . . C6 C 0.3167(3) -0.1025(4) 0.4193(2) 0.0654(8) Uani 1 1 d . . . . . H6A H 0.3226 -0.1388 0.3570 0.079 Uiso 1 1 calc R U . . . C7 C 0.3977(3) -0.1383(4) 0.5124(2) 0.0638(8) Uani 1 1 d . . . . . C8 C 0.5102(3) -0.2298(4) 0.5529(2) 0.0640(8) Uani 1 1 d . . . . . C9 C 0.5646(3) -0.3603(4) 0.4071(2) 0.0711(9) Uani 1 1 d . . . . . H9A H 0.4993 -0.3142 0.3565 0.085 Uiso 1 1 calc R U . . . C10 C 0.6471(3) -0.4615(4) 0.3835(3) 0.0753(10) Uani 1 1 d . . . . . H10A H 0.6370 -0.4866 0.3160 0.090 Uiso 1 1 calc R U . . . C11 C 0.7478(3) -0.5293(4) 0.4592(3) 0.0790(10) Uani 1 1 d . . . . . H11A H 0.8045 -0.5979 0.4415 0.095 Uiso 1 1 calc R U . . . C12 C 0.7631(3) -0.4956(4) 0.5582(3) 0.0767(10) Uani 1 1 d . . . . . H12A H 0.8299 -0.5411 0.6082 0.092 Uiso 1 1 calc R U . . . C13 C 0.6784(3) -0.3925(4) 0.5844(2) 0.0668(9) Uani 1 1 d . . . . . C14 C 0.5707(3) -0.2423(4) 0.6546(2) 0.0690(9) Uani 1 1 d . . . . . B1 B 0.4080(4) -0.0845(5) 0.7023(3) 0.0745(11) Uani 1 1 d . . . . . F1 F 0.4251(3) 0.0426(3) 0.75224(18) 0.1326(12) Uani 1 1 d . . . . . F2 F 0.3103(2) -0.1675(4) 0.73069(19) 0.1226(12) Uani 1 1 d . . . . . N1 N 0.2241(2) -0.0015(3) 0.43572(18) 0.0643(7) Uani 1 1 d . . . . . N2 N 0.3555(2) -0.0595(3) 0.58597(18) 0.0648(7) Uani 1 1 d . . . . . N3 N 0.5785(2) -0.3267(3) 0.50680(19) 0.0629(7) Uani 1 1 d . . . . . N4 N 0.6732(3) -0.3403(3) 0.6756(2) 0.0726(8) Uani 1 1 d . . . . . O1 O 0.5344(2) -0.1665(3) 0.72692(16) 0.0809(8) Uani 1 1 d . . . . . 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 C1 0.0508(15) 0.079(2) 0.0671(17) 0.0004(15) 0.0187(13) -0.0063(14) C2 0.0599(17) 0.090(2) 0.074(2) -0.0022(18) 0.0219(15) -0.0003(17) C3 0.0629(19) 0.088(2) 0.098(3) -0.002(2) 0.0275(18) 0.0093(18) C4 0.0622(18) 0.091(3) 0.089(2) 0.011(2) 0.0142(17) 0.0081(19) C5 0.0583(17) 0.090(2) 0.0706(19) 0.0072(17) 0.0120(14) 0.0025(17) C6 0.0546(16) 0.082(2) 0.0576(16) 0.0001(15) 0.0116(13) 0.0010(15) C7 0.0554(15) 0.077(2) 0.0584(16) 0.0012(15) 0.0137(13) -0.0048(15) C8 0.0509(15) 0.079(2) 0.0609(16) 0.0027(15) 0.0129(12) -0.0028(15) C9 0.0592(17) 0.093(2) 0.0597(17) 0.0019(16) 0.0129(14) -0.0010(17) C10 0.0617(17) 0.096(3) 0.0685(18) -0.0074(17) 0.0175(15) -0.0009(18) C11 0.0613(18) 0.089(3) 0.088(2) -0.0049(19) 0.0211(16) 0.0066(18) C12 0.0573(17) 0.092(2) 0.077(2) 0.0021(18) 0.0119(15) 0.0078(17) C13 0.0540(15) 0.083(2) 0.0594(17) 0.0041(15) 0.0077(13) -0.0035(15) C14 0.0566(17) 0.092(2) 0.0587(17) 0.0026(16) 0.0146(13) -0.0017(16) B1 0.073(2) 0.093(3) 0.0591(19) -0.0039(19) 0.0190(17) 0.001(2) F1 0.161(3) 0.125(2) 0.0840(15) -0.0307(15) -0.0185(16) 0.0411(19) F2 0.0832(15) 0.197(3) 0.0969(17) 0.0522(18) 0.0402(13) 0.0138(18) N1 0.0503(13) 0.0779(17) 0.0632(14) 0.0053(13) 0.0121(10) -0.0022(12) N2 0.0538(13) 0.0807(18) 0.0610(14) 0.0001(13) 0.0169(11) -0.0006(13) N3 0.0499(13) 0.0772(17) 0.0610(14) 0.0026(12) 0.0135(11) -0.0019(12) N4 0.0570(14) 0.095(2) 0.0622(15) 0.0041(14) 0.0091(12) 0.0061(14) O1 0.0686(14) 0.115(2) 0.0548(13) -0.0041(12) 0.0090(11) 0.0098(13) 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' B B 0.0013 0.0007 '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' F F 0.0171 0.0103 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 N2 C1 N1 108.1(3) . . N2 C1 C2 131.4(3) . . N1 C1 C2 120.4(3) . . C3 C2 C1 118.1(3) . . C3 C2 H2A 121.0 . . C1 C2 H2A 121.0 . . C2 C3 C4 120.8(3) . . C2 C3 H3A 119.6 . . C4 C3 H3A 119.6 . . C5 C4 C3 120.1(3) . . C5 C4 H4A 119.9 . . C3 C4 H4A 119.9 . . C4 C5 N1 119.1(3) . . C4 C5 H5A 120.4 . . N1 C5 H5A 120.4 . . C7 C6 N1 106.5(3) . . C7 C6 H6A 126.7 . . N1 C6 H6A 126.7 . . C6 C7 N2 108.7(3) . . C6 C7 C8 137.9(3) . . N2 C7 C8 113.4(3) . . C14 C8 N3 105.0(3) . . C14 C8 C7 123.6(3) . . N3 C8 C7 131.3(3) . . C10 C9 N3 119.0(3) . . C10 C9 H9A 120.5 . . N3 C9 H9A 120.5 . . C9 C10 C11 120.9(3) . . C9 C10 H10A 119.6 . . C11 C10 H10A 119.6 . . C12 C11 C10 120.5(3) . . C12 C11 H11A 119.7 . . C10 C11 H11A 119.7 . . C11 C12 C13 119.6(3) . . C11 C12 H12A 120.2 . . C13 C12 H12A 120.2 . . N4 C13 C12 131.0(3) . . N4 C13 N3 110.5(3) . . C12 C13 N3 118.5(3) . . O1 C14 N4 122.5(3) . . O1 C14 C8 124.5(3) . . N4 C14 C8 113.1(3) . . F1 B1 F2 110.2(3) . . F1 B1 O1 110.0(3) . . F2 B1 O1 108.0(3) . . F1 B1 N2 110.8(4) . . F2 B1 N2 106.5(3) . . O1 B1 N2 111.2(3) . . C1 N1 C5 121.4(3) . . C1 N1 C6 109.2(3) . . C5 N1 C6 129.4(3) . . C1 N2 C7 107.5(3) . . C1 N2 B1 127.0(3) . . C7 N2 B1 124.8(3) . . C9 N3 C8 131.7(3) . . C9 N3 C13 121.5(3) . . C8 N3 C13 106.7(3) . . C13 N4 C14 104.7(3) . . C14 O1 B1 119.9(3) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 N2 1.359(4) . C1 N1 1.366(4) . C1 C2 1.387(5) . C2 C3 1.369(5) . C2 H2A 0.9300 . C3 C4 1.404(6) . C3 H3A 0.9300 . C4 C5 1.351(5) . C4 H4A 0.9300 . C5 N1 1.372(4) . C5 H5A 0.9300 . C6 C7 1.366(4) . C6 N1 1.384(4) . C6 H6A 0.9300 . C7 N2 1.396(4) . C7 C8 1.415(5) . C8 C14 1.372(4) . C8 N3 1.381(4) . C9 C10 1.350(5) . C9 N3 1.368(4) . C9 H9A 0.9300 . C10 C11 1.402(5) . C10 H10A 0.9300 . C11 C12 1.356(5) . C11 H11A 0.9300 . C12 C13 1.392(5) . C12 H12A 0.9300 . C13 N4 1.350(4) . C13 N3 1.403(4) . C14 O1 1.338(4) . C14 N4 1.354(4) . B1 F1 1.342(5) . B1 F2 1.390(5) . B1 O1 1.457(5) . B1 N2 1.557(5) . 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 N2 C1 C2 C3 179.8(3) . . . . N1 C1 C2 C3 0.9(5) . . . . C1 C2 C3 C4 -1.0(6) . . . . C2 C3 C4 C5 0.7(6) . . . . C3 C4 C5 N1 -0.3(5) . . . . N1 C6 C7 N2 -0.1(4) . . . . N1 C6 C7 C8 -179.3(4) . . . . C6 C7 C8 C14 -179.7(4) . . . . N2 C7 C8 C14 1.2(5) . . . . C6 C7 C8 N3 -3.1(7) . . . . N2 C7 C8 N3 177.7(3) . . . . N3 C9 C10 C11 -1.4(5) . . . . C9 C10 C11 C12 0.8(6) . . . . C10 C11 C12 C13 -0.2(6) . . . . C11 C12 C13 N4 -179.7(4) . . . . C11 C12 C13 N3 0.3(5) . . . . N3 C8 C14 O1 -179.9(3) . . . . C7 C8 C14 O1 -2.5(6) . . . . N3 C8 C14 N4 0.3(4) . . . . C7 C8 C14 N4 177.7(3) . . . . N2 C1 N1 C5 -179.7(3) . . . . C2 C1 N1 C5 -0.5(5) . . . . N2 C1 N1 C6 0.2(4) . . . . C2 C1 N1 C6 179.3(3) . . . . C4 C5 N1 C1 0.2(5) . . . . C4 C5 N1 C6 -179.6(3) . . . . C7 C6 N1 C1 0.0(4) . . . . C7 C6 N1 C5 179.8(3) . . . . N1 C1 N2 C7 -0.3(3) . . . . C2 C1 N2 C7 -179.3(3) . . . . N1 C1 N2 B1 -170.8(3) . . . . C2 C1 N2 B1 10.3(6) . . . . C6 C7 N2 C1 0.3(4) . . . . C8 C7 N2 C1 179.7(3) . . . . C6 C7 N2 B1 171.0(3) . . . . C8 C7 N2 B1 -9.6(5) . . . . F1 B1 N2 C1 -50.6(5) . . . . F2 B1 N2 C1 69.3(5) . . . . O1 B1 N2 C1 -173.3(3) . . . . F1 B1 N2 C7 140.5(3) . . . . F2 B1 N2 C7 -99.7(4) . . . . O1 B1 N2 C7 17.7(5) . . . . C10 C9 N3 C8 179.9(3) . . . . C10 C9 N3 C13 1.5(5) . . . . C14 C8 N3 C9 -179.0(3) . . . . C7 C8 N3 C9 4.0(6) . . . . C14 C8 N3 C13 -0.4(3) . . . . C7 C8 N3 C13 -177.4(3) . . . . N4 C13 N3 C9 179.1(3) . . . . C12 C13 N3 C9 -0.9(5) . . . . N4 C13 N3 C8 0.3(4) . . . . C12 C13 N3 C8 -179.7(3) . . . . C12 C13 N4 C14 179.9(4) . . . . N3 C13 N4 C14 -0.1(4) . . . . O1 C14 N4 C13 -179.9(3) . . . . C8 C14 N4 C13 -0.1(4) . . . . N4 C14 O1 B1 -168.1(3) . . . . C8 C14 O1 B1 12.2(5) . . . . F1 B1 O1 C14 -141.1(3) . . . . F2 B1 O1 C14 98.6(4) . . . . N2 B1 O1 C14 -17.9(5) . . . .