#------------------------------------------------------------------------------ #$Date: 2022-03-21 10:47:39 +0200 (Mon, 21 Mar 2022) $ #$Revision: 273861 $ #$URL: file:///home/coder/svn-repositories/cod/cif/8/10/48/8104813.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_8104813 loop_ _publ_author_name 'Pan, Fei' 'Wei, Xian' 'Lv, Menglan Lan' _publ_section_title ; Crystal structure of (Z)-3-(6-bromo-1H-indol-3-yl)-1,3-diphenylprop-2-en-1-one, C23H16BrNO ; _journal_issue 2 _journal_name_full 'Zeitschrift f\"ur Kristallographie - New Crystal Structures' _journal_page_first 305 _journal_page_last 306 _journal_paper_doi 10.1515/ncrs-2020-0533 _journal_volume 236 _journal_year 2021 _chemical_formula_moiety 'C23 H16 Br N O' _chemical_formula_sum 'C23 H16 Br N O' _chemical_formula_weight 402.28 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _cell_angle_alpha 90.177(5) _cell_angle_beta 112.202(5) _cell_angle_gamma 95.167(5) _cell_formula_units_Z 2 _cell_length_a 9.914(3) _cell_length_b 10.141(3) _cell_length_c 10.179(3) _cell_measurement_reflns_used 1663 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 23.654 _cell_measurement_theta_min 2.857 _cell_volume 942.9(5) _computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)' _computing_data_reduction 'SAINT v8.34A (Bruker, 2013)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 296 _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0181 _diffrn_reflns_av_unetI/netI 0.0453 _diffrn_reflns_Laue_measured_fraction_full 0.986 _diffrn_reflns_Laue_measured_fraction_max 0.986 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 4715 _diffrn_reflns_point_group_measured_fraction_full 0.986 _diffrn_reflns_point_group_measured_fraction_max 0.986 _diffrn_reflns_theta_full 24.998 _diffrn_reflns_theta_max 24.998 _diffrn_reflns_theta_min 2.857 _exptl_absorpt_coefficient_mu 2.190 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.5947 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour 'clear yellowish yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier yellowish _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_meas . _exptl_crystal_description block _exptl_crystal_F_000 408 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.23 _refine_diff_density_max 0.923 _refine_diff_density_min -0.817 _refine_diff_density_rms 0.071 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 235 _refine_ls_number_reflns 3262 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.071 _refine_ls_R_factor_all 0.0797 _refine_ls_R_factor_gt 0.0520 _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^)+(0.0529P)^2^+1.4530P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1267 _refine_ls_wR_factor_ref 0.1351 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2338 _reflns_number_total 3262 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file suppl_j_ncrs-2020-0533_suppl.cif _cod_data_source_block 1 _cod_original_cell_volume 942.9(4) _cod_database_code 8104813 _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_max 0.633 _shelx_estimated_absorpt_t_min 0.600 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups 2.a Aromatic/amide H refined with riding coordinates: N1(H1a), C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C19(H19), C20(H20), C21(H21), C23(H23) ; _shelx_res_file ; TITL 1_a.res in P-1 1.res created by SHELXL-2018/3 at 08:55:00 on 10-Oct-2020 CELL 0.71073 9.9141 10.1411 10.1792 90.177 112.202 95.167 ZERR 2 0.0027 0.0028 0.0027 0.005 0.005 0.005 LATT 1 SFAC C H Br N O UNIT 46 32 2 2 2 EQIV $1 2-X,2-Y,1-Z L.S. 25 PLAN 6 SIZE 0.26 0.25 0.23 TEMP 23 HTAB C23 Br1_$1 BOND $H LIST 4 HTAB CONF fmap 2 acta OMIT 0 50 OMIT 0 1 0 OMIT -1 0 1 OMIT -1 0 3 REM REM REM WGHT 0.052900 1.453000 FVAR 0.66687 BR1 3 0.739903 0.987332 0.303661 11.00000 0.08453 0.03796 = 0.08889 0.01977 0.02084 0.00234 O1 5 0.686673 0.323042 0.273508 11.00000 0.02965 0.05747 = 0.03136 -0.00804 0.01296 -0.00470 N1 4 1.005495 0.605944 0.631482 11.00000 0.01840 0.04900 = 0.02949 -0.00530 0.00485 -0.00583 AFIX 43 H1A 2 1.093526 0.642946 0.671364 11.00000 -1.20000 AFIX 0 C1 1 0.758940 0.374421 0.832890 11.00000 0.03482 0.03900 = 0.03060 0.00243 0.01207 0.00369 AFIX 43 H1 2 0.767345 0.464771 0.818313 11.00000 -1.20000 AFIX 0 C2 1 0.762776 0.331416 0.963451 11.00000 0.04722 0.05996 = 0.02481 0.00096 0.01365 0.00413 AFIX 43 H2 2 0.772361 0.392605 1.035432 11.00000 -1.20000 AFIX 0 C3 1 0.752437 0.199206 0.985627 11.00000 0.06119 0.06285 = 0.03198 0.01808 0.01743 0.00480 AFIX 43 H3 2 0.753335 0.170343 1.072558 11.00000 -1.20000 AFIX 0 C4 1 0.740799 0.108884 0.881797 11.00000 0.06924 0.03819 = 0.04755 0.01300 0.01841 0.00809 AFIX 43 H4 2 0.737032 0.018928 0.899214 11.00000 -1.20000 AFIX 0 C5 1 0.734555 0.150309 0.750561 11.00000 0.04682 0.03754 = 0.03459 0.00178 0.01037 0.00285 AFIX 43 H5 2 0.724803 0.087905 0.679605 11.00000 -1.20000 AFIX 0 C6 1 0.742727 0.284341 0.723850 11.00000 0.02087 0.03723 = 0.02435 0.00195 0.00510 0.00343 C7 1 0.722512 0.331482 0.580062 11.00000 0.02435 0.03062 = 0.02610 0.00284 0.00960 0.00940 C8 1 0.618350 0.266848 0.466212 11.00000 0.02611 0.03497 = 0.03089 0.00021 0.00937 -0.00071 AFIX 43 H8 2 0.558949 0.199055 0.484508 11.00000 -1.20000 AFIX 0 C9 1 0.588038 0.291693 0.315641 11.00000 0.02833 0.03132 = 0.02810 -0.00313 0.01041 0.00276 C10 1 0.433221 0.275463 0.213670 11.00000 0.02642 0.03373 = 0.02484 -0.00580 0.00758 0.00564 C11 1 0.316139 0.249064 0.256477 11.00000 0.03032 0.04889 = 0.02695 -0.00732 0.00971 0.00431 AFIX 43 H11 2 0.333769 0.238204 0.352058 11.00000 -1.20000 AFIX 0 C12 1 0.174504 0.238911 0.158475 11.00000 0.03066 0.05812 = 0.04135 -0.00963 0.01090 0.00330 AFIX 43 H12 2 0.096971 0.219706 0.187817 11.00000 -1.20000 AFIX 0 C13 1 0.147214 0.257106 0.017053 11.00000 0.02828 0.07179 = 0.03722 -0.01323 -0.00112 0.01112 AFIX 43 H13 2 0.051381 0.251643 -0.048932 11.00000 -1.20000 AFIX 0 C14 1 0.261115 0.283133 -0.025807 11.00000 0.04381 0.09626 = 0.02610 0.00118 0.00680 0.01963 AFIX 43 H14 2 0.242556 0.293710 -0.121607 11.00000 -1.20000 AFIX 0 C15 1 0.403107 0.293937 0.070873 11.00000 0.03557 0.07258 = 0.02873 0.00002 0.01264 0.00499 AFIX 43 H15 2 0.479643 0.313807 0.040270 11.00000 -1.20000 AFIX 0 C16 1 0.810927 0.453731 0.574915 11.00000 0.02460 0.03469 = 0.02038 -0.00307 0.00901 0.00367 C17 1 0.767016 0.567689 0.490630 11.00000 0.02383 0.03254 = 0.02131 -0.00355 0.01137 0.00256 C18 1 0.891942 0.660010 0.530249 11.00000 0.02233 0.03590 = 0.02802 -0.00658 0.01142 -0.00106 C19 1 0.956029 0.484476 0.658313 11.00000 0.02813 0.03859 = 0.02668 -0.00033 0.00805 0.00708 AFIX 43 H19 2 1.013011 0.428911 0.724742 11.00000 -1.20000 AFIX 0 C20 1 0.635139 0.603806 0.391439 11.00000 0.02187 0.03706 = 0.03008 -0.00126 0.00971 -0.00134 AFIX 43 H20 2 0.551228 0.544434 0.362642 11.00000 -1.20000 AFIX 0 C21 1 0.630623 0.727331 0.337084 11.00000 0.03179 0.04383 = 0.03481 -0.00037 0.01014 0.00939 AFIX 43 H21 2 0.542875 0.752413 0.272124 11.00000 -1.20000 AFIX 0 C22 1 0.755995 0.815250 0.378248 11.00000 0.04732 0.02603 = 0.04770 0.00427 0.02261 0.00380 C23 1 0.889395 0.785828 0.475238 11.00000 0.03771 0.03843 = 0.04017 -0.00543 0.01585 -0.00868 AFIX 43 H23 2 0.972466 0.846126 0.502269 11.00000 -1.20000 AFIX 0 HKLF 4 REM 1_a.res in P-1 REM wR2 = 0.1351, GooF = S = 1.071, Restrained GooF = 1.071 for all data REM R1 = 0.0520 for 2338 Fo > 4sig(Fo) and 0.0797 for all 3262 data REM 235 parameters refined using 0 restraints END WGHT 0.0530 1.4414 REM Instructions for potential hydrogen bonds EQIV $2 -x+2, -y+1, -z+1 HTAB N1 O1_$2 HTAB C23 Br1_$1 REM Highest difference peak 0.923, deepest hole -0.817, 1-sigma level 0.071 Q1 1 0.8188 0.9668 0.2798 11.00000 0.05 0.92 Q2 1 0.7464 1.1377 0.3177 11.00000 0.05 0.74 Q3 1 0.7292 0.8306 0.2797 11.00000 0.05 0.51 Q4 1 0.6347 0.9723 0.2321 11.00000 0.05 0.39 Q5 1 0.7535 0.9537 0.3739 11.00000 0.05 0.37 Q6 1 0.7567 0.3022 0.3391 11.00000 0.05 0.34 ; _shelx_hkl_file ; 2 0 0 9999.00 179.48 -3 0 0 532.25 9.90 3 0 0 488.75 10.20 -4 0 0 2010.40 35.70 4 0 0 1937.91 36.10 -5 0 0 3.60 1.40 5 0 0 2.90 2.00 -6 0 0 862.81 16.70 6 0 0 822.12 17.40 -7 0 0 115.39 5.10 7 0 0 117.19 6.10 8 0 0 286.47 9.70 9 0 0 11.80 4.70 10 0 0 18.30 5.70 11 0 0 -0.30 5.90 11 -1 0 2.50 6.20 10 -1 0 4.00 5.40 9 -1 0 20.00 5.00 8 -1 0 8.30 4.10 7 -1 0 73.59 5.70 -7 1 0 75.49 3.90 6 -1 0 289.07 8.00 -6 1 0 283.57 6.80 5 -1 0 887.61 17.70 -5 1 0 889.11 16.80 4 -1 0 224.78 5.60 -4 1 0 207.48 4.80 3 -1 0 963.30 17.80 -3 1 0 932.91 17.20 1 -1 0 68.99 1.80 0 1 0 2.50 0.40 1 1 0 139.09 3.10 -2 -1 0 2895.61 52.49 2 1 0 2862.91 52.69 -3 -1 0 1134.79 20.50 3 1 0 1081.09 20.70 -4 -1 0 742.93 14.70 4 1 0 772.52 15.10 5 1 0 3.20 2.10 -6 -1 0 177.18 5.70 6 1 0 169.08 6.30 -7 -1 0 18.70 2.90 7 1 0 21.40 3.60 -8 -1 0 66.39 5.60 8 1 0 81.69 5.90 9 1 0 27.00 5.20 10 1 0 27.80 5.90 11 1 0 4.30 5.90 11 -2 0 3.40 6.10 10 -2 0 6.20 5.60 9 -2 0 11.10 4.90 8 -2 0 22.30 4.60 7 -2 0 -0.10 3.30 6 -2 0 26.00 3.40 -6 2 0 22.10 1.90 5 -2 0 13.90 2.40 -5 2 0 13.80 1.40 4 -2 0 1404.76 26.30 3 -2 0 128.39 3.80 2 -2 0 39.50 2.10 1 -2 0 1126.69 20.10 -1 2 0 1099.19 20.30 0 -2 0 1223.28 22.30 0 -2 0 1245.58 22.20 0 2 0 1219.08 22.30 -1 -2 0 138.49 3.60 1 2 0 146.29 3.60 -2 -2 0 308.87 6.70 2 2 0 301.97 6.60 -3 -2 0 196.38 5.10 3 2 0 186.98 5.00 -4 -2 0 868.81 17.00 4 2 0 853.61 17.00 -5 -2 0 24.70 2.50 5 2 0 32.30 3.20 -6 -2 0 16.80 2.70 6 2 0 18.80 3.30 -7 -2 0 45.60 3.90 7 2 0 48.30 4.60 -8 -2 0 1.20 3.00 8 2 0 -3.00 3.90 -9 -2 0 -4.20 3.30 9 2 0 3.30 4.60 10 2 0 25.80 6.00 11 2 0 4.40 6.40 11 -3 0 11.90 6.50 10 -3 0 -1.50 5.30 9 -3 0 0.80 4.60 8 -3 0 46.80 5.10 7 -3 0 2.70 3.30 6 -3 0 117.39 5.30 5 -3 0 7.50 2.30 4 -3 0 296.27 7.30 3 -3 0 98.49 3.50 -2 3 0 2200.88 39.80 1 -3 0 1250.17 22.60 -1 3 0 1236.18 22.90 0 -3 0 3049.59 53.69 0 3 0 2966.10 53.69 -1 -3 0 35.40 2.40 1 3 0 28.10 2.40 -2 -3 0 342.57 7.60 2 3 0 333.57 7.50 -3 -3 0 482.15 10.40 3 3 0 482.55 10.40 -4 -3 0 116.29 4.70 4 3 0 106.59 4.50 -5 -3 0 113.69 5.30 5 3 0 120.19 5.30 -6 -3 0 290.07 8.80 6 3 0 301.37 9.00 -7 -3 0 215.48 8.20 7 3 0 232.58 8.60 -8 -3 0 86.39 6.50 8 3 0 92.39 7.50 -9 -3 0 9.30 4.10 9 3 0 24.40 5.70 10 3 0 1.80 5.60 11 3 0 4.50 6.50 11 -4 0 -2.00 6.50 10 -4 0 22.80 6.20 9 -4 0 69.69 6.90 8 -4 0 4.00 4.20 7 -4 0 27.60 4.10 6 -4 0 72.79 5.00 5 -4 0 2.80 2.40 -4 4 0 3.10 2.30 -3 4 0 -1.70 1.90 -2 4 0 227.78 5.90 -1 4 0 176.48 5.00 0 -4 0 1868.61 34.10 0 4 0 1849.81 34.10 -1 -4 0 44.70 3.20 1 4 0 37.40 3.00 -2 -4 0 624.44 13.30 2 4 0 652.93 13.20 -3 -4 0 26.90 2.70 3 4 0 23.20 2.80 -4 -4 0 76.09 4.80 4 4 0 76.19 4.70 -5 -4 0 14.90 3.10 5 4 0 11.80 3.30 -6 -4 0 101.89 6.40 6 4 0 93.39 6.50 -7 -4 0 13.30 3.70 7 4 0 14.40 4.40 -8 -4 0 1.30 3.70 8 4 0 4.80 4.70 -9 -4 0 27.60 4.90 9 4 0 36.30 6.30 -10 -4 0 -4.30 4.50 10 4 0 6.70 6.10 10 -5 0 -1.50 6.10 9 -5 0 28.90 6.00 8 -5 0 124.39 8.30 7 -5 0 15.90 4.10 -6 5 0 127.19 6.80 -5 5 0 31.60 3.70 -4 5 0 554.74 12.50 -3 5 0 392.06 9.40 -2 5 0 794.42 16.10 -1 5 0 1959.90 36.30 0 -5 0 291.67 7.40 0 5 0 282.07 7.40 -1 -5 0 327.57 8.40 1 5 0 333.47 8.30 -2 -5 0 213.58 6.90 2 5 0 217.08 6.60 -3 -5 0 306.27 8.70 3 5 0 300.67 8.30 -4 -5 0 226.48 7.90 4 5 0 214.18 7.50 -5 -5 0 95.09 6.60 5 5 0 87.89 6.10 -6 -5 0 9.80 3.90 6 5 0 7.60 4.10 -7 -5 0 -3.70 3.70 7 5 0 9.30 4.60 -8 -5 0 33.80 5.30 8 5 0 54.19 6.70 -9 -5 0 -1.90 4.60 9 5 0 9.20 5.90 -10 -5 0 3.80 5.20 10 5 0 18.20 6.90 -10 6 0 32.20 7.30 -9 6 0 17.20 6.40 -8 6 0 32.50 5.90 -7 6 0 8.60 4.50 -6 6 0 272.37 9.30 -5 6 0 113.89 6.40 -4 6 0 719.33 15.80 -2 6 0 471.15 11.10 -1 6 0 483.85 11.40 0 -6 0 342.27 9.30 0 6 0 364.36 9.30 -1 -6 0 308.77 8.80 1 6 0 307.97 8.60 -2 -6 0 610.44 14.20 2 6 0 616.14 13.90 3 6 0 177.18 7.20 -4 -6 0 226.18 8.70 4 6 0 240.28 8.50 -5 -6 0 201.08 9.00 5 6 0 188.98 8.40 -6 -6 0 102.99 8.30 6 6 0 123.39 7.90 -7 -6 0 34.80 5.70 7 6 0 38.90 6.10 -8 -6 0 -2.20 5.00 8 6 0 -2.80 5.70 -9 -6 0 -3.50 5.50 9 6 0 -2.50 6.60 -10 -6 0 -2.60 6.10 10 6 0 9.10 7.00 -10 7 0 2.70 7.00 -9 7 0 0.20 6.10 -8 7 0 30.20 6.10 -7 7 0 17.50 5.30 -6 7 0 144.69 8.10 -5 7 0 185.28 8.10 -4 7 0 138.79 7.10 -3 7 0 17.50 4.10 -2 7 0 243.68 8.50 -1 7 0 143.59 6.80 0 7 0 584.44 13.90 -1 -7 0 212.28 8.30 1 7 0 199.28 7.90 -2 -7 0 324.97 10.50 2 7 0 324.17 9.90 -3 -7 0 184.18 8.80 3 7 0 185.28 8.10 -4 -7 0 128.99 8.40 4 7 0 127.09 7.60 -5 -7 0 25.30 5.10 5 7 0 28.20 5.40 -6 -7 0 66.19 6.70 6 7 0 85.49 7.10 -7 -7 0 149.49 11.30 7 7 0 150.48 9.90 -8 -7 0 18.20 6.80 8 7 0 36.00 6.90 -9 -7 0 22.90 7.60 9 7 0 46.50 8.30 -9 8 0 1.20 6.60 -8 8 0 28.60 6.50 -7 8 0 2.90 5.20 -6 8 0 4.70 4.80 -5 8 0 26.40 5.00 -4 8 0 50.89 5.50 -3 8 0 49.00 5.30 -2 8 0 182.68 8.50 -1 8 0 235.88 9.10 0 8 0 186.78 8.30 -1 -8 0 182.98 9.30 1 8 0 180.78 8.40 -2 -8 0 5.10 4.40 2 8 0 8.80 4.60 -3 -8 0 232.88 10.50 3 8 0 244.98 9.60 -4 -8 0 23.40 5.40 4 8 0 27.60 5.50 -5 -8 0 51.19 6.60 5 8 0 53.39 6.50 -6 -8 0 7.50 6.10 6 8 0 16.20 6.00 -7 -8 0 -8.00 6.50 7 8 0 12.60 6.40 -8 -8 0 0.50 7.50 8 8 0 21.40 7.30 -8 9 0 6.40 6.50 -7 9 0 1.80 6.10 -6 9 0 74.19 7.30 -5 9 0 38.70 6.20 -4 9 0 107.59 8.50 -3 9 0 86.29 6.80 -2 9 0 312.17 11.10 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4 -0.30 5.60 -6 -8 4 30.90 5.80 -5 -8 4 99.49 8.90 -4 -8 4 33.70 5.20 -3 -8 4 181.88 8.00 -3 -8 4 155.38 8.50 -2 -8 4 104.39 7.40 -2 -8 4 107.09 6.00 1 8 -4 95.79 6.80 -1 -8 4 90.69 6.70 -1 -8 4 110.59 6.20 0 8 -4 117.59 7.10 0 -8 4 119.59 6.80 -1 8 -4 75.09 5.80 1 -8 4 73.09 5.40 -2 8 -4 78.39 5.90 2 -8 4 76.69 5.80 -3 8 -4 192.38 8.70 3 -8 4 210.38 9.00 -4 8 -4 83.19 6.50 4 -8 4 86.29 6.70 -5 8 -4 76.89 7.00 5 -8 4 73.39 7.10 -6 8 -4 0.90 5.70 6 -8 4 -5.70 5.90 -7 8 -4 3.70 6.30 -10 -7 4 8.20 7.30 -9 -7 4 37.50 7.00 -8 -7 4 33.40 6.30 -7 -7 4 31.20 5.60 -6 -7 4 2.00 4.20 -5 -7 4 6.70 4.00 -4 -7 4 21.40 4.00 -3 -7 4 28.40 4.10 -3 -7 4 34.70 3.50 2 7 -4 11.40 3.70 -2 -7 4 16.50 3.30 -2 -7 4 13.40 3.60 1 7 -4 240.08 7.90 -1 -7 4 239.88 7.60 -1 -7 4 235.38 8.00 0 7 -4 12.90 3.70 0 -7 4 10.30 3.50 -1 7 -4 55.79 4.70 1 -7 4 51.39 4.60 -2 7 -4 10.70 3.80 2 -7 4 4.90 3.70 -3 7 -4 8.30 4.10 3 -7 4 8.20 4.00 -4 7 -4 4.20 4.30 4 -7 4 0.40 4.20 -5 7 -4 55.39 6.00 5 -7 4 50.59 6.00 -6 7 -4 6.70 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4 91.09 6.10 5 -4 4 88.19 6.60 6 -4 4 8.90 4.70 6 -4 4 10.90 3.90 7 -4 4 -0.30 3.90 7 -4 4 -1.50 5.30 8 -4 4 5.60 6.30 9 -4 4 -4.00 6.80 -12 -3 4 0.10 4.90 -11 -3 4 7.30 4.70 -10 -3 4 0.10 4.00 -9 -3 4 45.20 5.00 -8 -3 4 53.39 4.60 -7 -3 4 77.99 5.80 -6 -3 4 10.60 2.80 -6 -3 4 14.90 2.20 5 3 -4 568.74 11.30 -5 -3 4 577.74 13.00 -5 -3 4 568.74 11.70 4 3 -4 49.10 2.10 -4 -3 4 41.50 3.10 -4 -3 4 52.29 3.90 3 3 -4 808.12 14.60 -3 -3 4 797.62 16.20 -3 -3 4 792.42 15.70 2 3 -4 89.49 2.70 -2 -3 4 92.49 3.90 -2 -3 4 93.39 3.80 1 3 -4 1826.12 32.80 -1 -3 4 1825.92 33.40 -1 -3 4 1831.22 33.70 0 -3 4 283.07 6.20 0 -3 4 270.57 7.00 1 -3 4 1148.49 22.10 1 -3 4 1155.18 21.70 2 -3 4 121.39 4.70 2 -3 4 122.09 4.90 3 -3 4 545.75 12.10 3 -3 4 544.85 12.20 4 -3 4 78.99 5.40 4 -3 4 80.49 5.20 5 -3 4 415.26 11.20 5 -3 4 381.56 10.30 6 -3 4 5.00 4.40 6 -3 4 6.40 3.40 7 -3 4 109.39 8.90 7 -3 4 115.09 6.80 8 -3 4 8.80 6.10 9 -3 4 18.50 7.10 -12 -2 4 4.20 4.50 -11 -2 4 1.80 4.00 -10 -2 4 13.60 4.20 -9 -2 4 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155.68 6.20 8 -1 -4 3.00 2.80 -8 1 4 1.40 2.50 7 -1 -4 75.99 4.20 -7 1 4 62.39 4.10 6 -1 -4 76.29 3.70 -6 1 4 66.39 3.70 -5 1 4 71.99 3.10 -5 1 4 72.69 3.50 -4 1 4 1.50 1.50 -4 1 4 1.60 1.30 -3 1 4 997.80 18.30 -3 1 4 1001.60 18.90 -2 1 4 673.33 12.60 -2 1 4 661.53 13.00 -1 1 4 230.18 5.50 -1 1 4 231.48 5.20 0 1 4 100.59 3.50 0 1 4 100.59 3.40 1 1 4 577.84 11.80 1 1 4 563.24 11.50 2 1 4 111.29 4.20 2 1 4 120.59 4.60 3 1 4 194.38 6.50 3 1 4 190.38 5.50 4 1 4 60.79 3.70 4 1 4 61.49 5.30 5 1 4 164.28 7.40 6 1 4 32.40 5.10 7 1 4 35.90 6.00 8 1 4 27.20 6.40 9 1 4 18.20 7.20 11 -2 -4 3.50 4.70 10 -2 -4 12.90 4.30 -10 2 4 7.90 3.40 -10 2 4 12.00 3.70 9 -2 -4 107.19 6.50 8 -2 -4 7.10 3.00 -6 2 4 5.20 2.40 -5 2 4 110.59 4.30 -5 2 4 116.39 4.10 -4 2 4 196.48 5.30 -4 2 4 189.78 5.00 -3 2 4 907.61 17.40 -3 2 4 911.81 17.20 -2 2 4 646.94 12.80 -2 2 4 654.83 12.70 -1 2 4 1009.80 18.90 -1 2 4 983.20 18.70 0 2 4 42.40 2.60 0 2 4 44.30 3.00 1 2 4 233.18 6.30 1 2 4 227.58 5.70 2 2 4 -1.60 2.40 2 2 4 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11 33.20 6.30 0 0 11 0.60 5.80 1 0 11 59.19 7.00 -10 1 11 -1.20 6.20 -9 1 11 9.20 6.30 -8 1 11 -8.30 5.80 -7 1 11 1.20 5.70 -6 1 11 1.00 5.60 -5 1 11 -0.50 5.60 -4 1 11 -11.00 5.30 -3 1 11 2.50 5.40 -2 1 11 12.00 5.70 -1 1 11 -6.20 5.40 0 1 11 0.10 5.50 1 1 11 -1.30 5.70 -10 2 11 1.30 6.80 -9 2 11 -2.60 6.50 -8 2 11 2.70 6.30 -7 2 11 7.60 6.10 -6 2 11 4.60 5.80 -5 2 11 4.70 5.60 -4 2 11 10.20 5.80 -3 2 11 4.90 5.60 -2 2 11 -4.10 5.20 -1 2 11 -5.20 5.20 0 2 11 -2.60 5.30 -10 3 11 1.10 7.40 -9 3 11 6.30 7.00 -8 3 11 2.50 6.50 -7 3 11 -6.00 6.00 -6 3 11 4.10 6.00 -5 3 11 0.90 5.70 -4 3 11 22.00 6.10 -3 3 11 10.80 5.90 -2 3 11 31.30 5.90 -1 3 11 4.30 5.50 -9 4 11 -6.00 7.30 -8 4 11 8.60 7.10 -7 4 11 17.20 6.70 -6 4 11 13.30 6.30 -5 4 11 -0.70 5.90 -4 4 11 -1.40 5.70 -3 4 11 -0.60 5.70 -2 4 11 11.20 5.70 -1 4 11 3.10 5.40 -9 5 11 -6.80 7.30 -8 5 11 17.00 7.50 -7 5 11 80.09 8.60 -6 5 11 4.50 6.60 -5 5 11 16.60 6.70 -4 5 11 18.90 6.40 -3 5 11 15.20 6.10 -2 5 11 2.70 5.70 -8 6 11 38.60 8.20 -7 6 11 4.90 7.20 -6 6 11 3.50 7.00 -5 6 11 3.80 6.50 -4 6 11 4.70 6.30 -3 6 11 -4.40 5.80 -6 7 11 -1.40 7.30 -5 7 11 3.70 7.20 -4 7 11 0.70 6.40 -6 -5 12 5.20 8.40 -6 -5 12 12.70 7.20 -5 -5 12 3.00 7.30 -4 -5 12 -5.00 7.20 -3 -5 12 6.40 7.20 -2 -5 12 8.20 7.40 -7 -4 12 4.60 5.80 -7 -4 12 -0.20 6.60 -6 -4 12 19.10 5.70 -6 -4 12 7.50 7.00 -5 -4 12 0.80 7.00 -4 -4 12 1.50 7.00 -3 -4 12 -2.90 7.00 -2 -4 12 12.00 7.50 -1 -4 12 10.30 7.20 -8 -3 12 15.30 6.70 -8 -3 12 22.50 6.20 -7 -3 12 -4.70 6.60 -6 -3 12 4.50 6.80 -5 -3 12 -0.90 6.70 -4 -3 12 2.20 6.90 -3 -3 12 -10.90 6.70 -2 -3 12 9.30 7.30 -1 -3 12 21.10 7.60 0 -3 12 -4.70 7.30 -8 -2 12 -3.30 6.40 -7 -2 12 3.90 6.70 -6 -2 12 -0.40 6.40 -5 -2 12 5.20 6.80 -4 -2 12 -6.50 6.30 -3 -2 12 25.00 7.10 -2 -2 12 4.60 7.00 -1 -2 12 -1.20 6.90 0 -2 12 2.30 7.20 -9 -1 12 0.30 6.60 -8 -1 12 2.20 6.70 -7 -1 12 1.20 6.70 -6 -1 12 4.00 6.70 -5 -1 12 3.70 6.50 -4 -1 12 -0.40 6.50 -3 -1 12 -2.60 6.50 -2 -1 12 25.90 7.10 -1 -1 12 8.60 7.00 0 -1 12 27.30 7.50 -9 0 12 5.40 7.00 -8 0 12 0.40 6.80 -7 0 12 13.10 6.90 -6 0 12 15.40 6.70 -5 0 12 16.50 6.80 -4 0 12 -2.10 6.40 -3 0 12 15.40 6.80 -2 0 12 7.30 6.70 -1 0 12 22.70 7.10 0 0 12 4.20 6.70 -9 1 12 0.50 7.10 -8 1 12 5.30 7.10 -7 1 12 18.70 7.20 -6 1 12 20.40 7.00 -5 1 12 -2.00 6.30 -4 1 12 -1.40 6.40 -3 1 12 -2.80 6.30 -2 1 12 -8.60 6.30 -1 1 12 2.60 6.40 0 1 12 -8.10 6.20 -9 2 12 -5.70 7.20 -8 2 12 -10.70 6.90 -7 2 12 4.20 6.80 -6 2 12 -8.60 6.40 -5 2 12 -6.60 6.60 -4 2 12 0.30 6.40 -3 2 12 0.50 6.30 -2 2 12 0.40 6.20 -1 2 12 -6.10 6.10 0 2 12 -9.90 8.10 -8 3 12 4.30 7.20 -7 3 12 -5.20 7.00 -6 3 12 2.90 6.70 -5 3 12 -4.60 6.70 -4 3 12 11.50 6.90 -3 3 12 4.20 6.40 -2 3 12 1.70 6.10 -1 3 12 -2.60 5.90 -8 4 12 17.60 7.90 -7 4 12 -5.40 7.00 -6 4 12 -2.70 7.10 -5 4 12 -4.10 6.80 -4 4 12 -5.80 6.70 -3 4 12 1.50 6.40 -2 4 12 15.20 6.40 -7 5 12 16.70 7.60 -6 5 12 6.10 7.40 -5 5 12 0.50 7.10 -4 5 12 7.70 7.00 -3 5 12 0.30 6.60 -6 -2 13 1.10 7.70 -5 -2 13 -0.60 7.50 -4 -2 13 28.70 8.30 -6 -1 13 16.20 8.00 -5 -1 13 0.90 7.40 -4 -1 13 -5.10 7.50 -3 -1 13 -5.50 7.30 -7 0 13 9.50 7.70 -6 0 13 8.80 7.70 -5 0 13 2.40 7.40 -4 0 13 -5.50 7.30 -3 0 13 15.10 7.80 -6 1 13 15.00 7.70 -5 1 13 -2.60 7.10 -4 1 13 26.30 7.80 -3 1 13 4.80 7.50 -6 2 13 -3.30 7.50 -5 2 13 6.60 7.40 -4 2 13 -11.70 7.30 0 0 0 0.00 0.00 _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 Br1 Br 0.73990(7) 0.98733(5) 0.30366(7) 0.0742(3) Uani 1 1 d . . . . . O1 O 0.6867(3) 0.3230(3) 0.2735(3) 0.0397(7) Uani 1 1 d . . . . . N1 N 1.0055(3) 0.6059(3) 0.6315(3) 0.0342(8) Uani 1 1 d . . . . . H1A H 1.093526 0.642946 0.671364 0.041 Uiso 1 1 calc R . . . . C1 C 0.7589(4) 0.3744(4) 0.8329(4) 0.0349(10) Uani 1 1 d . . . . . H1 H 0.767345 0.464771 0.818313 0.042 Uiso 1 1 calc R . . . . C2 C 0.7628(5) 0.3314(5) 0.9635(4) 0.0441(11) Uani 1 1 d . . . . . H2 H 0.772361 0.392605 1.035432 0.053 Uiso 1 1 calc R . . . . C3 C 0.7524(5) 0.1992(5) 0.9856(5) 0.0521(13) Uani 1 1 d . . . . . H3 H 0.753335 0.170343 1.072558 0.063 Uiso 1 1 calc R . . . . C4 C 0.7408(6) 0.1089(5) 0.8818(5) 0.0526(13) Uani 1 1 d . . . . . H4 H 0.737032 0.018928 0.899214 0.063 Uiso 1 1 calc R . . . . C5 C 0.7346(5) 0.1503(4) 0.7506(5) 0.0412(11) Uani 1 1 d . . . . . H5 H 0.724803 0.087905 0.679605 0.049 Uiso 1 1 calc R . . . . C6 C 0.7427(4) 0.2843(4) 0.7239(4) 0.0285(9) Uani 1 1 d . . . . . C7 C 0.7225(4) 0.3315(4) 0.5801(4) 0.0266(8) Uani 1 1 d . . . . . C8 C 0.6183(4) 0.2668(4) 0.4662(4) 0.0313(9) Uani 1 1 d . . . . . H8 H 0.558949 0.199055 0.484508 0.038 Uiso 1 1 calc R . . . . C9 C 0.5880(4) 0.2917(4) 0.3156(4) 0.0294(9) Uani 1 1 d . . . . . C10 C 0.4332(4) 0.2755(4) 0.2137(4) 0.0288(9) Uani 1 1 d . . . . . C11 C 0.3161(4) 0.2491(4) 0.2565(4) 0.0357(10) Uani 1 1 d . . . . . H11 H 0.333769 0.238204 0.352058 0.043 Uiso 1 1 calc R . . . . C12 C 0.1745(5) 0.2389(5) 0.1585(5) 0.0443(11) Uani 1 1 d . . . . . H12 H 0.096971 0.219706 0.187817 0.053 Uiso 1 1 calc R . . . . C13 C 0.1472(5) 0.2571(5) 0.0171(5) 0.0494(12) Uani 1 1 d . . . . . H13 H 0.051381 0.251643 -0.048932 0.059 Uiso 1 1 calc R . . . . C14 C 0.2611(5) 0.2831(6) -0.0258(5) 0.0565(14) Uani 1 1 d . . . . . H14 H 0.242556 0.293710 -0.121607 0.068 Uiso 1 1 calc R . . . . C15 C 0.4031(5) 0.2939(5) 0.0709(4) 0.0455(12) Uani 1 1 d . . . . . H15 H 0.479643 0.313807 0.040270 0.055 Uiso 1 1 calc R . . . . C16 C 0.8109(4) 0.4537(4) 0.5749(4) 0.0264(8) Uani 1 1 d . . . . . C17 C 0.7670(4) 0.5677(4) 0.4906(4) 0.0251(8) Uani 1 1 d . . . . . C18 C 0.8919(4) 0.6600(4) 0.5302(4) 0.0285(9) Uani 1 1 d . . . . . C19 C 0.9560(4) 0.4845(4) 0.6583(4) 0.0316(9) Uani 1 1 d . . . . . H19 H 1.013011 0.428911 0.724742 0.038 Uiso 1 1 calc R . . . . C20 C 0.6351(4) 0.6038(4) 0.3914(4) 0.0300(9) Uani 1 1 d . . . . . H20 H 0.551228 0.544434 0.362642 0.036 Uiso 1 1 calc R . . . . C21 C 0.6306(5) 0.7273(4) 0.3371(4) 0.0372(10) Uani 1 1 d . . . . . H21 H 0.542875 0.752413 0.272124 0.045 Uiso 1 1 calc R . . . . C22 C 0.7560(5) 0.8153(4) 0.3782(5) 0.0390(10) Uani 1 1 d . . . . . C23 C 0.8894(5) 0.7858(4) 0.4752(5) 0.0393(10) Uani 1 1 d . . . . . H23 H 0.972466 0.846126 0.502269 0.047 Uiso 1 1 calc R . . . . 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 Br1 0.0845(5) 0.0380(3) 0.0889(5) 0.0198(3) 0.0208(4) 0.0023(3) O1 0.0296(16) 0.0575(19) 0.0314(16) -0.0080(14) 0.0130(13) -0.0047(14) N1 0.0184(17) 0.049(2) 0.0295(18) -0.0053(16) 0.0048(15) -0.0058(15) C1 0.035(2) 0.039(2) 0.031(2) 0.0024(18) 0.0121(19) 0.0037(19) C2 0.047(3) 0.060(3) 0.025(2) 0.001(2) 0.014(2) 0.004(2) C3 0.061(3) 0.063(3) 0.032(3) 0.018(2) 0.017(2) 0.005(3) C4 0.069(3) 0.038(3) 0.048(3) 0.013(2) 0.018(3) 0.008(2) C5 0.047(3) 0.038(2) 0.035(2) 0.0018(19) 0.010(2) 0.003(2) C6 0.021(2) 0.037(2) 0.024(2) 0.0020(17) 0.0051(16) 0.0034(17) C7 0.024(2) 0.031(2) 0.026(2) 0.0028(16) 0.0096(17) 0.0094(16) C8 0.026(2) 0.035(2) 0.031(2) 0.0002(18) 0.0094(18) -0.0007(17) C9 0.028(2) 0.031(2) 0.028(2) -0.0031(17) 0.0104(18) 0.0028(17) C10 0.026(2) 0.034(2) 0.025(2) -0.0058(17) 0.0076(17) 0.0056(17) C11 0.030(2) 0.049(3) 0.027(2) -0.0073(19) 0.0097(19) 0.0043(19) C12 0.031(2) 0.058(3) 0.041(3) -0.010(2) 0.011(2) 0.003(2) C13 0.028(2) 0.072(3) 0.037(3) -0.013(2) -0.001(2) 0.011(2) C14 0.044(3) 0.096(4) 0.026(2) 0.001(2) 0.007(2) 0.020(3) C15 0.036(3) 0.073(3) 0.029(2) 0.000(2) 0.013(2) 0.005(2) C16 0.025(2) 0.035(2) 0.0204(19) -0.0031(16) 0.0090(17) 0.0037(17) C17 0.024(2) 0.033(2) 0.0213(19) -0.0035(16) 0.0114(17) 0.0026(16) C18 0.022(2) 0.036(2) 0.028(2) -0.0066(17) 0.0114(17) -0.0011(17) C19 0.028(2) 0.039(2) 0.027(2) -0.0003(17) 0.0081(18) 0.0071(18) C20 0.022(2) 0.037(2) 0.030(2) -0.0013(17) 0.0097(17) -0.0013(17) C21 0.032(2) 0.044(3) 0.035(2) -0.0004(19) 0.0101(19) 0.0094(19) C22 0.047(3) 0.026(2) 0.048(3) 0.0043(19) 0.023(2) 0.0038(19) C23 0.038(3) 0.038(2) 0.040(3) -0.0054(19) 0.016(2) -0.009(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' Br Br -0.2901 2.4595 '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_ _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 C18 N1 H1A 125.8 . . C19 N1 H1A 125.8 . . C19 N1 C18 108.4(3) . . C2 C1 H1 119.6 . . C6 C1 H1 119.6 . . C6 C1 C2 120.8(4) . . C1 C2 H2 120.2 . . C3 C2 C1 119.7(4) . . C3 C2 H2 120.2 . . C2 C3 H3 119.7 . . C4 C3 C2 120.6(4) . . C4 C3 H3 119.7 . . C3 C4 H4 119.9 . . C3 C4 C5 120.3(4) . . C5 C4 H4 119.9 . . C4 C5 H5 119.7 . . C4 C5 C6 120.5(4) . . C6 C5 H5 119.7 . . C1 C6 C5 118.0(4) . . C1 C6 C7 120.1(4) . . C5 C6 C7 121.7(4) . . C8 C7 C6 118.8(3) . . C8 C7 C16 124.7(3) . . C16 C7 C6 116.3(3) . . C7 C8 H8 116.4 . . C7 C8 C9 127.1(4) . . C9 C8 H8 116.4 . . O1 C9 C8 121.7(4) . . O1 C9 C10 120.1(3) . . C8 C9 C10 118.2(3) . . C11 C10 C9 122.7(3) . . C15 C10 C9 119.0(4) . . C15 C10 C11 118.3(4) . . C10 C11 H11 119.8 . . C12 C11 C10 120.5(4) . . C12 C11 H11 119.8 . . C11 C12 H12 119.9 . . C11 C12 C13 120.2(4) . . C13 C12 H12 119.9 . . C12 C13 H13 120.1 . . C14 C13 C12 119.7(4) . . C14 C13 H13 120.1 . . C13 C14 H14 119.6 . . C13 C14 C15 120.7(4) . . C15 C14 H14 119.6 . . C10 C15 H15 119.7 . . C14 C15 C10 120.5(4) . . C14 C15 H15 119.7 . . C17 C16 C7 129.1(3) . . C19 C16 C7 125.3(3) . . C19 C16 C17 105.5(3) . . C18 C17 C16 106.4(3) . . C20 C17 C16 135.0(3) . . C20 C17 C18 118.5(3) . . N1 C18 C17 108.4(3) . . N1 C18 C23 128.8(4) . . C23 C18 C17 122.8(4) . . N1 C19 C16 111.3(3) . . N1 C19 H19 124.4 . . C16 C19 H19 124.4 . . C17 C20 H20 120.3 . . C21 C20 C17 119.4(4) . . C21 C20 H20 120.3 . . C20 C21 H21 119.8 . . C20 C21 C22 120.4(4) . . C22 C21 H21 119.8 . . C21 C22 Br1 118.0(3) . . C23 C22 Br1 118.8(3) . . C23 C22 C21 123.1(4) . . C18 C23 H23 122.1 . . C22 C23 C18 115.8(4) . . C22 C23 H23 122.1 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Br1 C22 1.901(4) . O1 C9 1.226(5) . N1 H1A 0.8600 . N1 C18 1.367(5) . N1 C19 1.352(5) . C1 H1 0.9300 . C1 C2 1.388(6) . C1 C6 1.387(6) . C2 H2 0.9300 . C2 C3 1.361(7) . C3 H3 0.9300 . C3 C4 1.361(7) . C4 H4 0.9300 . C4 C5 1.382(6) . C5 H5 0.9300 . C5 C6 1.388(6) . C6 C7 1.487(5) . C7 C8 1.345(5) . C7 C16 1.465(5) . C8 H8 0.9300 . C8 C9 1.473(6) . C9 C10 1.487(5) . C10 C11 1.391(5) . C10 C15 1.386(6) . C11 H11 0.9300 . C11 C12 1.376(6) . C12 H12 0.9300 . C12 C13 1.377(6) . C13 H13 0.9300 . C13 C14 1.362(7) . C14 H14 0.9300 . C14 C15 1.374(6) . C15 H15 0.9300 . C16 C17 1.441(5) . C16 C19 1.372(5) . C17 C18 1.409(5) . C17 C20 1.398(5) . C18 C23 1.393(6) . C19 H19 0.9300 . C20 H20 0.9300 . C20 C21 1.369(6) . C21 H21 0.9300 . C21 C22 1.386(6) . C22 C23 1.378(6) . C23 H23 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 C23 H23 Br1 0.93 3.12 4.007(4) 159.9 2_776 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 Br1 C22 C23 C18 177.3(3) . . . . O1 C9 C10 C11 -175.4(4) . . . . O1 C9 C10 C15 1.2(6) . . . . N1 C18 C23 C22 -176.9(4) . . . . C1 C2 C3 C4 1.1(7) . . . . C1 C6 C7 C8 -134.8(4) . . . . C1 C6 C7 C16 40.0(5) . . . . C2 C1 C6 C5 -1.7(6) . . . . C2 C1 C6 C7 173.3(4) . . . . C2 C3 C4 C5 -2.1(8) . . . . C3 C4 C5 C6 1.2(7) . . . . C4 C5 C6 C1 0.7(6) . . . . C4 C5 C6 C7 -174.2(4) . . . . C5 C6 C7 C8 40.0(5) . . . . C5 C6 C7 C16 -145.2(4) . . . . C6 C1 C2 C3 0.9(7) . . . . C6 C7 C8 C9 -175.4(4) . . . . C6 C7 C16 C17 -134.1(4) . . . . C6 C7 C16 C19 42.5(5) . . . . C7 C8 C9 O1 36.8(6) . . . . C7 C8 C9 C10 -144.3(4) . . . . C7 C16 C17 C18 177.4(4) . . . . C7 C16 C17 C20 0.9(7) . . . . C7 C16 C19 N1 -178.1(3) . . . . C8 C7 C16 C17 40.3(6) . . . . C8 C7 C16 C19 -143.0(4) . . . . C8 C9 C10 C11 5.6(6) . . . . C8 C9 C10 C15 -177.8(4) . . . . C9 C10 C11 C12 178.0(4) . . . . C9 C10 C15 C14 -178.3(4) . . . . C10 C11 C12 C13 -1.1(7) . . . . C11 C10 C15 C14 -1.5(7) . . . . C11 C12 C13 C14 1.0(7) . . . . C12 C13 C14 C15 -1.2(8) . . . . C13 C14 C15 C10 1.5(8) . . . . C15 C10 C11 C12 1.4(6) . . . . C16 C7 C8 C9 10.3(6) . . . . C16 C17 C18 N1 0.4(4) . . . . C16 C17 C18 C23 -176.9(4) . . . . C16 C17 C20 C21 175.5(4) . . . . C17 C16 C19 N1 -0.8(4) . . . . C17 C18 C23 C22 -0.1(6) . . . . C17 C20 C21 C22 1.0(6) . . . . C18 N1 C19 C16 1.1(4) . . . . C18 C17 C20 C21 -0.7(5) . . . . C19 N1 C18 C17 -0.9(4) . . . . C19 N1 C18 C23 176.2(4) . . . . C19 C16 C17 C18 0.2(4) . . . . C19 C16 C17 C20 -176.3(4) . . . . C20 C17 C18 N1 177.6(3) . . . . C20 C17 C18 C23 0.3(6) . . . . C20 C21 C22 Br1 -177.7(3) . . . . C20 C21 C22 C23 -0.8(7) . . . . C21 C22 C23 C18 0.4(6) . . . .