#------------------------------------------------------------------------------ #$Date: 2022-09-23 05:09:46 +0300 (Fri, 23 Sep 2022) $ #$Revision: 278105 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/24/41/2244179.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2244179 loop_ _publ_author_name 'Archana, Sreeramapura D.' 'Kiran Kumar, Haruvegowda' 'Shankara Prasad, Holehundi J.' 'Yathirajan, Hemmige S.' 'Parkin, Sean' _publ_section_title ; Synthesis and crystal structures of 1-benzoyl-4-(4-nitrophenyl)piperazine and 1-(4-bromobenzoyl)-4-phenylpiperazine at 90K ; _journal_coeditor_code TX2058 _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first ; ; _journal_paper_doi 10.1107/S2056989022009008 _journal_volume 78 _journal_year 2022 _chemical_absolute_configuration ad _chemical_formula_iupac 'C17 H17 Br N2 O' _chemical_formula_moiety 'C17 H17 Br N2 O' _chemical_formula_sum 'C17 H17 Br N2 O' _chemical_formula_weight 345.23 _chemical_name_systematic ; 1-(4-Bromobenzoyl)-4-phenylpiperazine ; _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 difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method 'SHELXL-2019/2 and CIFFIX' _cell_angle_alpha 90 _cell_angle_beta 98.6250(10) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.5162(3) _cell_length_b 6.1125(2) _cell_length_c 15.7249(5) _cell_measurement_reflns_used 9856 _cell_measurement_temperature 90.0(2) _cell_measurement_theta_max 27.47 _cell_measurement_theta_min 2.62 _cell_volume 714.28(4) _computing_cell_refinement ; APEX3 (Bruker, 2016) ; _computing_data_collection ; APEX3 (Bruker, 2016) ; _computing_data_reduction ; APEX3 (Bruker, 2016) ; _computing_molecular_graphics ; XP in SHELXTL (Sheldrick, 2008) ; _computing_publication_material ; SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010) ; _computing_structure_refinement ; SHELXL2019/2 (Sheldrick, 2015b) ; _computing_structure_solution ; SHELXT (Sheldrick, 2015a) ; _diffrn_ambient_temperature 90.0(2) _diffrn_detector_area_resol_mean 7.41 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker D8 Venture dual source' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0650 _diffrn_reflns_av_unetI/netI 0.0367 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 6918 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.504 _diffrn_reflns_theta_min 2.620 _diffrn_source microsource _exptl_absorpt_coefficient_mu 2.878 _exptl_absorpt_correction_T_max 0.806 _exptl_absorpt_correction_T_min 0.568 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (TWINABS; Sheldrick, 2012) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.605 _exptl_crystal_description 'slab cut from lath' _exptl_crystal_F_000 352 _exptl_crystal_size_max 0.350 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.060 _refine_diff_density_max 0.293 _refine_diff_density_min -0.222 _refine_ls_abs_structure_details ; Flack x determined using 1306 quotients [(I^+^)-(I^-^)]/[(I^+^)+(I^-^)] (Parsons et al., 2013) ; _refine_ls_abs_structure_Flack 0.012(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 191 _refine_ls_number_reflns 6918 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all 0.0266 _refine_ls_R_factor_gt 0.0225 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0158P)^2^+0.0999P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.0491 _reflns_number_gt 6410 _reflns_number_total 6918 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file tx2058sup1.cif _cod_data_source_block II _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 2244179 _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 0.432 _shelx_estimated_absorpt_t_max 0.846 _shelx_hkl_file ; 1 0 0 201.065 4.87581 2 1 0 0 422.570 17.8935 -2 1 0 0 422.570 17.8935 1 1 0 0 224.094 5.78314 1 2 0 0 4992.35 200.349 -2 2 0 0 4992.35 200.349 1 2 0 0 2612.32 53.3638 1 2 0 0 2599.53 53.1178 2 3 0 0 4.96110 1.23779 2 3 0 0 5.04421 1.29799 1 4 0 0 190.307 4.98747 1 4 0 0 178.386 4.53211 2 5 0 0 933.898 17.7409 1 5 0 0 921.959 18.1734 2 6 0 0 430.196 9.79697 2 6 0 0 449.357 10.3396 1 7 0 0 409.487 12.2985 1 7 0 0 368.533 11.2976 2 8 0 0 103.086 7.76715 2 8 0 0 110.309 7.58909 1 9 0 0 254.907 11.8050 2 9 0 0 245.640 12.7137 1 0 -1 0 0.16635 0.41368 2 0 -1 0 0.13423 0.36899 1 0 1 0 0.63691 0.50509 2 0 1 0 0.86699 0.45681 1 0 1 0 1.32433 0.95269 -2 0 1 0 1.32433 0.95269 1 -1 -1 0 6130.51 350.543 1 -2 -1 0 2774.50 62.8419 1 -2 -1 0 5240.33 235.030 -2 -2 -1 0 5240.33 235.030 1 -2 -1 0 2652.79 52.8095 2 2 1 0 3105.95 85.7246 1 2 1 0 2980.21 90.9829 2 2 1 0 6041.06 165.689 -2 2 1 0 6041.06 165.689 1 -3 -1 0 609.653 12.1975 1 -3 -1 0 584.721 11.5372 2 -3 -1 0 1199.66 73.9763 -2 -3 -1 0 1199.66 73.9763 1 3 1 0 579.015 12.1497 1 3 1 0 548.695 11.4919 2 -4 -1 0 305.788 6.92792 1 -4 -1 0 297.476 7.22881 2 4 1 0 267.431 6.71772 1 4 1 0 248.916 6.47008 2 -5 -1 0 291.703 7.38231 2 -5 -1 0 298.282 7.45072 1 5 1 0 270.099 6.49747 2 5 1 0 282.470 7.38322 1 -6 -1 0 117.148 4.37647 2 -6 -1 0 116.466 4.77265 1 6 1 0 103.973 4.04713 2 6 1 0 114.802 4.55915 1 -7 -1 0 106.102 6.95029 1 -7 -1 0 90.1439 6.56481 2 7 1 0 87.6401 5.39001 2 7 1 0 101.992 5.46054 1 -8 -1 0 496.430 16.2674 2 -8 -1 0 520.814 17.9257 1 8 1 0 545.799 17.9499 1 8 1 0 518.563 14.9120 2 -9 -1 0 291.448 12.6911 2 -9 -1 0 300.499 13.6277 1 9 1 0 306.235 15.1359 1 9 1 0 269.936 12.7610 2 0 -2 0 1079.74 26.1663 1 0 -2 0 1032.27 24.8154 2 0 2 0 1213.35 26.1993 1 0 2 0 1147.02 24.8936 2 -1 -2 0 1414.15 24.0487 1 -1 -2 0 1345.44 22.3011 2 1 2 0 1514.67 24.2078 1 1 2 0 1459.50 23.1418 2 -2 -2 0 456.027 8.83563 1 -2 -2 0 431.492 8.37447 2 2 2 0 492.718 8.57564 1 2 2 0 472.052 8.19741 2 -3 -2 0 336.269 7.29169 1 -3 -2 0 303.063 6.45977 2 3 2 0 350.282 7.77405 1 3 2 0 325.196 7.22617 2 -4 -2 0 178.990 5.14015 1 -4 -2 0 168.101 4.72693 2 4 2 0 209.547 9.56244 2 4 2 0 254.951 5.77646 1 -5 -2 0 375.618 8.86497 1 -5 -2 0 354.609 7.85706 2 5 2 0 323.944 7.68540 2 5 2 0 363.654 8.42568 1 -6 -2 0 654.252 14.8269 2 -6 -2 0 687.288 16.2333 1 6 2 0 667.966 14.5786 1 6 2 0 646.447 14.2896 2 -7 -2 0 505.992 14.2633 1 -7 -2 0 471.727 13.6799 2 7 2 0 477.701 13.8968 1 7 2 0 445.967 11.8614 2 -8 -2 0 8.73274 5.51398 1 -8 -2 0 12.9486 5.73088 2 8 2 0 7.03564 3.52691 2 8 2 0 3.41959 4.21795 1 -9 -2 0 57.6335 8.98724 2 -9 -2 0 76.4539 12.8192 1 9 2 0 58.9472 6.45727 2 9 2 0 73.1516 8.61582 1 0 -3 0 1.45329 1.12325 2 0 -3 0 1.73832 0.92114 1 0 3 0 1.94359 0.93406 1 0 3 0 0.21280 1.00526 2 -1 -3 0 180.003 4.32647 1 -1 -3 0 170.584 4.40707 2 1 3 0 212.019 5.22922 2 1 3 0 216.583 5.39913 1 -2 -3 0 986.095 18.2979 1 -2 -3 0 956.019 15.9849 2 2 3 0 876.866 14.9340 2 2 3 0 947.813 16.6242 1 -3 -3 0 568.174 12.1252 2 -3 -3 0 596.760 11.5753 1 3 3 0 603.270 11.2283 2 3 3 0 638.775 11.3427 1 -4 -3 0 245.280 5.65790 2 -4 -3 0 257.743 6.66886 1 4 3 0 263.479 6.15007 1 4 3 0 252.531 5.91041 2 -5 -3 0 286.090 7.30705 2 -5 -3 0 305.382 7.83517 1 5 3 0 295.318 7.81163 2 5 3 0 316.940 7.50675 1 -6 -3 0 6.37645 3.47403 2 -6 -3 0 5.65279 3.52100 1 6 3 0 11.4207 2.84205 2 6 3 0 26.8696 3.94760 1 -7 -3 0 311.355 10.6748 2 -7 -3 0 321.154 11.1728 1 7 3 0 331.366 10.3628 2 7 3 0 375.153 11.6624 1 -8 -3 0 334.063 12.1015 1 -8 -3 0 343.369 14.5379 2 8 3 0 331.177 11.5736 1 8 3 0 319.398 15.3804 2 0 -4 0 1724.93 39.0681 2 0 -4 0 1744.48 43.7533 1 0 4 0 1651.94 50.1469 2 0 4 0 1741.39 76.2868 1 -1 -4 0 488.228 9.49937 1 -1 -4 0 459.110 8.78942 2 1 4 0 390.128 11.6880 2 1 4 0 411.303 10.6890 1 -2 -4 0 2.46760 1.76768 2 -2 -4 0 3.70678 1.89658 1 2 4 0 10.1363 2.27392 1 2 4 0 9.37187 2.15293 2 -3 -4 0 473.253 9.05913 2 -3 -4 0 507.966 10.3530 1 3 4 0 478.395 9.72362 1 3 4 0 440.021 10.7615 2 -4 -4 0 142.110 4.44859 2 -4 -4 0 138.443 5.14584 1 4 4 0 197.068 5.22893 1 4 4 0 185.911 4.34418 2 -5 -4 0 381.670 11.0929 2 -5 -4 0 390.110 11.9813 1 5 4 0 491.143 11.3647 2 5 4 0 532.623 11.8073 1 -6 -4 0 473.667 12.7259 1 -6 -4 0 457.996 15.3705 2 6 4 0 431.241 12.7260 1 6 4 0 395.898 10.4691 2 -7 -4 0 141.187 8.74084 2 -7 -4 0 152.691 7.56718 1 7 4 0 149.068 7.90698 1 7 4 0 132.995 8.44717 2 -8 -4 0 1.22545 7.48382 2 -8 -4 0 8.02596 6.29016 1 8 4 0 8.14900 7.75203 2 8 4 0 5.20250 7.57347 1 0 -5 0 0.06625 1.38246 2 0 -5 0 5.35011 7.06049 1 0 5 0 -2.9526 4.76780 2 0 5 0 -1.2947 5.45107 1 -1 -5 0 827.354 17.1121 2 -1 -5 0 878.587 20.3285 1 1 5 0 845.287 24.1899 1 1 5 0 766.411 19.0360 2 -2 -5 0 980.735 22.5679 1 -2 -5 0 929.919 21.7305 2 2 5 0 825.071 22.3996 2 2 5 0 869.477 20.4538 1 -3 -5 0 1.54246 5.05581 1 -3 -5 0 2.38833 3.22876 2 3 5 0 23.9483 4.51558 2 3 5 0 30.7820 4.20148 1 -4 -5 0 370.198 8.81395 2 -4 -5 0 382.977 10.2662 1 4 5 0 494.843 12.7886 1 4 5 0 467.785 21.0812 2 -5 -5 0 136.734 5.23170 1 -5 -5 0 135.773 4.84868 2 5 5 0 119.518 4.60190 2 5 5 0 122.226 4.97033 1 -6 -5 0 3.34400 4.30775 1 -6 -5 0 3.63580 4.08375 2 6 5 0 4.25722 3.49228 1 6 5 0 6.13757 4.14343 2 -7 -5 0 184.170 9.69576 2 -7 -5 0 179.437 17.9905 1 7 5 0 143.973 9.95867 2 7 5 0 162.737 9.75200 1 0 -6 0 960.415 33.6573 1 0 -6 0 915.746 32.6072 2 0 6 0 892.422 48.9377 1 0 6 0 857.877 44.5351 2 -1 -6 0 493.151 11.3983 1 -1 -6 0 465.357 12.1847 2 1 6 0 461.013 16.3847 2 1 6 0 503.969 19.1411 1 -2 -6 0 23.5294 3.46695 2 -2 -6 0 29.3784 5.23342 1 2 6 0 55.6566 4.47275 2 2 6 0 58.3030 5.53583 1 -3 -6 0 14.6834 3.49745 2 -3 -6 0 18.8286 4.22328 1 3 6 0 11.7422 4.14097 2 3 6 0 13.9191 5.08983 1 -4 -6 0 115.767 5.89404 1 -4 -6 0 104.901 5.12779 2 4 6 0 128.203 9.93601 2 4 6 0 135.880 8.75981 1 -5 -6 0 170.735 7.91638 1 -5 -6 0 182.024 7.31862 2 5 6 0 142.434 11.7445 1 5 6 0 128.917 14.0485 2 -6 -6 0 107.912 7.55110 1 -6 -6 0 92.3096 9.39043 2 6 6 0 126.508 17.3887 2 6 6 0 129.152 18.0538 1 0 -7 0 3.23575 7.76363 2 0 -7 0 -6.8511 3.92383 1 0 7 0 -5.3846 15.1833 1 0 7 0 0.45941 17.2064 2 -1 -7 0 149.424 4.62061 2 -1 -7 0 158.602 8.96578 1 1 7 0 140.251 14.6055 1 1 7 0 123.572 25.3179 2 -2 -7 0 362.240 11.2468 1 -2 -7 0 344.203 11.7323 2 2 7 0 413.294 19.3828 1 2 7 0 384.458 22.3410 2 -3 -7 0 202.865 10.1496 1 -3 -7 0 203.764 7.19012 2 3 7 0 200.870 13.1123 2 3 7 0 229.811 21.1275 1 -4 -7 0 83.3094 8.19519 1 -4 -7 0 73.3425 5.83223 2 4 7 0 46.7738 15.1837 2 4 7 0 69.4674 15.4233 1 -9 0 1 110.538 8.62979 2 -9 0 1 126.928 9.01439 1 -8 0 1 3.86677 5.31846 2 -8 0 1 9.53676 4.77364 1 -7 0 1 18.2747 4.68945 1 -7 0 1 17.7250 4.05849 2 -6 0 1 948.347 21.2743 2 -6 0 1 979.358 18.9992 1 -5 0 1 1190.00 21.6875 2 -5 0 1 1231.17 22.6377 1 -4 0 1 1028.22 18.7781 1 -4 0 1 992.987 17.9887 2 -3 0 1 23.6505 1.70936 1 -3 0 1 20.2965 1.47721 2 -2 0 1 4351.61 174.802 -2 -2 0 1 4351.61 174.802 1 -2 0 1 2213.29 41.0260 1 -2 0 1 2156.54 39.9025 2 -1 0 1 467.966 10.0562 2 -1 0 1 467.130 12.6915 1 -1 0 1 910.707 22.0838 -2 -1 0 1 910.707 22.0838 1 1 0 1 18.3169 0.97861 1 1 0 1 19.5301 1.01227 2 1 0 1 34.0092 2.58966 -2 1 0 1 34.0092 2.58966 1 2 0 1 5905.31 236.677 -2 2 0 1 5905.31 236.677 1 2 0 1 2814.96 61.6216 2 2 0 1 3193.87 69.4386 1 3 0 1 119.202 3.84331 1 3 0 1 110.674 3.90943 2 4 0 1 119.357 4.26847 2 4 0 1 127.540 4.36531 1 5 0 1 874.930 16.9131 1 5 0 1 832.351 16.5076 2 6 0 1 860.687 16.8895 2 6 0 1 890.116 18.3526 1 7 0 1 282.644 9.71974 2 7 0 1 303.619 10.1762 1 8 0 1 9.05122 5.46574 1 8 0 1 6.93819 5.68589 2 9 0 1 32.5047 7.20824 2 9 0 1 25.9954 6.79624 1 9 -1 -1 222.225 11.0218 2 9 -1 -1 209.063 10.9887 1 -9 1 1 241.706 11.6112 1 -9 1 1 213.266 12.1846 2 8 -1 -1 356.789 13.3674 2 8 -1 -1 360.733 13.1393 1 -8 1 1 395.956 12.6046 1 -8 1 1 362.509 10.9993 2 7 -1 -1 164.327 8.01154 2 7 -1 -1 171.501 8.31903 1 -7 1 1 128.006 6.31381 2 -7 1 1 135.996 6.57405 1 6 -1 -1 651.326 13.9718 2 6 -1 -1 686.859 15.4515 1 -6 1 1 789.632 15.0395 1 -6 1 1 747.791 14.7926 2 5 -1 -1 88.1173 3.72004 1 5 -1 -1 80.2575 3.48195 2 -5 1 1 79.2196 3.79086 1 -5 1 1 78.5809 3.04729 2 4 -1 -1 1510.43 32.6999 2 4 -1 -1 1583.17 32.4162 1 -4 1 1 1820.13 31.3506 1 -4 1 1 1749.14 31.4049 2 3 -1 -1 3965.02 65.7890 2 3 -1 -1 4074.32 66.5709 1 -3 1 1 3602.36 66.2711 2 -3 1 1 3804.97 77.1939 1 2 -1 -1 2538.26 43.1549 2 2 -1 -1 2654.87 42.1377 1 -2 1 1 2169.50 45.6234 2 -2 1 1 2267.28 51.5437 1 -2 1 1 4233.44 172.978 -2 -2 1 1 4233.44 172.978 1 1 -1 -1 77.1528 1.65303 1 1 -1 -1 71.7115 1.57974 2 -1 1 1 392.054 17.2540 -2 -1 1 1 392.054 17.2540 1 0 -1 -1 194.475 3.56733 2 0 -1 -1 208.455 3.85385 1 0 -1 -1 401.096 26.4590 -2 0 -1 -1 401.096 26.4590 1 0 1 1 449.787 15.6065 -2 0 1 1 449.787 15.6065 1 0 1 1 225.212 5.12004 2 0 1 1 235.991 5.33703 1 -1 -1 -1 718.408 13.6521 1 -1 -1 -1 686.428 14.4732 2 -1 -1 -1 1445.71 88.5346 -2 -1 -1 -1 1445.71 88.5346 1 1 1 1 802.622 14.4411 1 1 1 1 771.438 13.3389 2 1 1 1 1589.65 66.7692 -2 1 1 1 1589.65 66.7692 1 -2 -1 -1 720.252 15.1513 2 -2 -1 -1 756.094 16.5653 1 2 1 1 1085.45 26.9426 -2 2 1 1 1085.45 26.9426 1 2 1 1 581.795 40.4372 2 2 1 1 585.617 29.5944 1 -3 -1 -1 1978.71 41.2994 1 -3 -1 -1 1905.13 39.9616 2 -3 -1 -1 4004.69 135.986 -2 -3 -1 -1 4004.69 135.986 1 3 1 1 1965.17 46.6977 2 3 1 1 1999.46 48.3787 1 3 1 1 4067.66 117.212 -2 3 1 1 4067.66 117.212 1 -4 -1 -1 1030.15 19.7820 1 -4 -1 -1 991.625 20.0649 2 4 1 1 1055.16 19.8691 1 4 1 1 1038.39 19.3289 2 -5 -1 -1 688.005 13.6916 2 -5 -1 -1 730.800 14.4492 1 5 1 1 656.877 14.2162 1 5 1 1 629.963 13.5126 2 -6 -1 -1 53.5746 3.70656 2 -6 -1 -1 57.6632 3.89951 1 6 1 1 69.2599 3.95334 1 6 1 1 63.9164 3.48522 2 -7 -1 -1 279.405 10.6204 2 -7 -1 -1 298.073 11.2956 1 7 1 1 289.655 9.56586 2 7 1 1 324.024 10.0905 1 -8 -1 -1 150.044 8.84301 2 -8 -1 -1 161.834 9.06271 1 8 1 1 188.816 8.88836 2 8 1 1 199.636 9.24353 1 -9 -1 -1 78.9019 8.34109 2 -9 -1 -1 86.7529 8.95785 1 9 1 1 60.9547 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49.7820 6.58310 2 1 0 18 44.5485 6.77483 1 2 0 18 9.71070 6.18033 2 2 0 18 13.5931 6.67750 1 3 0 18 9.03225 8.00857 2 3 0 18 16.1484 7.85397 1 5 -1 -18 90.0140 7.91621 2 5 -1 -18 56.7644 9.58966 1 -5 1 18 30.9217 9.27107 1 -5 1 18 40.5642 8.03422 2 4 -1 -18 191.475 9.45053 2 4 -1 -18 198.873 10.4205 1 -4 1 18 227.698 11.4697 1 -4 1 18 203.591 10.6905 2 3 -1 -18 160.066 9.20878 1 3 -1 -18 134.949 8.13164 2 -3 1 18 121.663 9.89552 1 -3 1 18 121.086 8.24598 2 2 -1 -18 163.795 7.19431 1 2 -1 -18 148.172 8.20545 2 -2 1 18 146.423 7.30966 2 -2 1 18 150.824 8.23686 1 1 -1 -18 14.0687 4.55659 2 1 -1 -18 9.93248 4.67687 1 -1 1 18 28.5121 5.68708 1 -1 1 18 16.9719 5.12812 2 0 -1 -18 85.5959 6.89689 2 0 -1 -18 97.9824 7.36823 1 0 1 18 83.7664 6.28481 2 0 1 18 71.5939 6.82766 1 -1 -1 -18 191.413 9.20881 2 -1 -1 -18 207.432 10.8339 1 1 1 18 158.729 8.82332 1 1 1 18 148.034 8.55514 2 -2 -1 -18 49.2654 9.06245 2 -2 -1 -18 38.0109 8.34507 1 2 1 18 41.8984 6.56398 1 2 1 18 43.3169 6.50597 2 -3 -1 -18 83.1270 8.40822 1 -3 -1 -18 80.6816 8.30852 2 3 1 18 102.603 9.51145 1 3 1 18 115.226 8.40159 2 5 -2 -18 78.4608 9.84238 1 5 -2 -18 64.1783 8.16588 2 -5 2 18 102.342 9.65072 2 -5 2 18 76.4030 10.1778 1 4 -2 -18 12.7018 7.10533 2 4 -2 -18 29.2387 10.1568 1 -4 2 18 13.8944 8.04352 1 -4 2 18 10.8952 5.82028 2 3 -2 -18 -1.4974 5.57544 2 3 -2 -18 4.20466 6.23255 1 -3 2 18 1.07369 5.26981 2 -3 2 18 2.77978 7.24820 1 2 -2 -18 50.6402 3.78982 2 2 -2 -18 55.1669 4.43041 1 -2 2 18 51.0237 5.46664 2 -2 2 18 59.7851 6.56963 1 1 -2 -18 751.169 19.5859 1 1 -2 -18 704.031 19.2951 2 -1 2 18 718.466 20.2411 2 -1 2 18 729.663 25.8736 1 0 -2 -18 85.2744 6.41929 2 0 -2 -18 82.9795 6.59626 1 0 2 18 66.2985 6.65022 1 0 2 18 64.2435 5.98662 2 -1 -2 -18 7.99221 6.16605 2 -1 -2 -18 1.88312 7.14182 1 1 2 18 -3.1355 5.09142 2 1 2 18 3.90605 6.22833 1 -2 -2 -18 81.7095 8.05744 2 -2 -2 -18 110.990 10.4405 1 2 2 18 69.1910 7.07388 2 2 2 18 79.0088 8.21417 1 4 -3 -18 103.307 12.3796 2 4 -3 -18 121.997 13.9289 1 -4 3 18 73.2425 23.5939 1 -4 3 18 111.793 22.0555 2 3 -3 -18 125.572 11.4201 1 3 -3 -18 123.224 9.22763 2 -3 3 18 109.575 9.74367 1 -3 3 18 99.3297 11.2259 2 2 -3 -18 73.2158 9.93490 1 2 -3 -18 88.5544 8.71549 2 -2 3 18 77.8375 7.80645 1 -2 3 18 62.5556 8.82767 2 1 -3 -18 28.3326 7.33028 2 1 -3 -18 32.6119 8.64332 1 -1 3 18 21.6211 6.67584 1 -1 3 18 25.1433 5.98854 2 0 -3 -18 235.276 14.8392 2 0 -3 -18 238.065 15.2085 1 0 3 18 207.771 11.1885 2 0 3 18 210.541 11.7554 1 -1 -3 -18 289.660 14.5652 2 -1 -3 -18 291.192 15.3373 1 1 3 18 331.802 14.5976 1 1 3 18 306.574 15.4542 2 -4 0 19 -2.6948 9.18864 1 -4 0 19 2.44831 6.40898 2 -3 0 19 4.07072 6.93001 2 -3 0 19 2.94174 7.23459 1 -2 0 19 42.4956 5.60979 1 -2 0 19 32.5865 4.59848 2 -1 0 19 396.992 13.6388 1 -1 0 19 387.654 13.9373 2 0 0 19 179.373 8.70862 2 0 0 19 188.781 10.1286 1 1 0 19 14.0649 5.88687 1 1 0 19 3.10923 7.09018 2 2 0 19 10.3431 7.48417 1 2 0 19 7.18148 7.58004 2 4 -1 -19 191.784 9.78075 2 4 -1 -19 190.663 11.8645 1 -4 1 19 183.176 12.1686 1 -4 1 19 191.884 9.75551 2 3 -1 -19 161.233 9.95123 1 3 -1 -19 161.850 10.8887 2 -3 1 19 159.043 11.7565 1 -3 1 19 171.795 9.50472 2 2 -1 -19 226.058 9.23053 1 2 -1 -19 205.295 9.80225 2 -2 1 19 220.292 8.95626 2 -2 1 19 229.115 11.7123 1 1 -1 -19 6.86513 4.54745 2 1 -1 -19 12.9434 7.05462 1 -1 1 19 3.87615 5.03685 2 -1 1 19 10.0295 5.71976 1 0 -1 -19 21.3120 8.15594 1 0 -1 -19 35.9554 7.34737 2 0 1 19 21.9136 5.63040 2 0 1 19 16.7919 6.39453 1 -1 -1 -19 91.5040 9.37033 2 -1 -1 -19 98.6735 8.90307 1 1 1 19 118.861 9.44723 1 1 1 19 101.395 7.47884 2 3 -2 -19 46.5287 7.68032 2 3 -2 -19 28.9582 8.43184 1 -3 2 19 41.5005 9.64429 1 -3 2 19 23.7823 6.61935 2 2 -2 -19 88.4138 8.75907 1 2 -2 -19 85.0577 9.03540 2 -2 2 19 99.9356 6.52971 2 -2 2 19 100.670 8.20489 1 1 -2 -19 131.619 9.56120 1 1 -2 -19 115.343 9.01051 2 -1 2 19 147.062 7.95134 2 -1 2 19 178.686 10.0153 1 0 -2 -19 44.1641 6.86585 2 0 -2 -19 42.6744 8.05505 1 0 2 19 26.3920 5.99180 2 0 2 19 36.0110 7.38179 1 -1 -2 -19 103.913 9.76863 2 -1 -2 -19 136.550 10.0576 1 1 2 19 134.161 9.74010 1 1 2 19 123.791 8.37595 2 -3 0 20 4.69458 7.02310 2 -3 0 20 20.3689 8.25790 1 -2 0 20 65.8286 6.41910 1 -2 0 20 66.6482 8.38483 2 -1 0 20 66.7034 7.70984 2 -1 0 20 98.8776 7.51708 1 0 0 20 89.5067 7.13761 2 0 0 20 98.4850 8.14867 1 3 -1 -20 245.649 28.9581 1 3 -1 -20 221.521 27.5734 2 -3 1 20 208.996 28.1261 2 -3 1 20 225.266 41.5996 1 2 -1 -20 177.370 10.9251 2 2 -1 -20 167.620 12.7436 1 -2 1 20 182.360 13.1064 1 -2 1 20 168.422 8.45936 2 1 -1 -20 10.3786 6.15871 2 1 -1 -20 1.59049 6.45112 1 -1 1 20 3.41028 5.54185 2 -1 1 20 -0.9132 6.14806 1 0 -1 -20 1.16344 6.03992 1 0 -1 -20 3.17060 7.86222 2 0 1 20 -3.9420 6.27984 2 0 1 20 -7.0875 6.63883 1 0 0 0 0.00 0.00 0 ; _shelx_hkl_checksum 76395 _shelx_res_file ; TITL m22123 : space group P21 m22123.res created by SHELXL-2019/2 at 09:33:53 on 01-Sep-2022 CELL 0.71073 7.5162 6.1125 15.7249 90.000 98.625 90.000 ZERR 2 0.0003 0.0002 0.0005 0.000 0.001 0.000 LATT -1 SYMM -X, 1/2+Y, -Z SFAC C H BR N O UNIT 34 34 2 4 2 TEMP -183 SIZE 0.35 0.20 0.06 REM FORM slab cut from lath REM COLR colourless MERG 0 L.S. 10 ACTA BOND $H LIST 6 CONF HTAB REM Various planes for dihedrals etc. MPLA C5 C6 C7 C8 C9 C10 MPLA 6 C12 C13 C14 C15 C16 C17 Br1 REM Torsion angle: RTAB tors N1 C11 C12 C13 EQIV $2 x, y-1, z HTAB C13 O1_$2 HTAB C14 O1_$2 HTAB FMAP 2 PLAN 20 REM EXTI 0.000000 not needed. WGHT 0.015800 0.099900 BASF 0.48604 FVAR 1.08994 BR1 3 0.090547 0.112863 0.950387 11.00000 0.01541 0.01942 = 0.02254 0.00283 0.00626 -0.00119 O1 5 0.672997 0.884387 0.839924 11.00000 0.02691 0.01401 = 0.03359 -0.00649 0.01451 -0.00233 N1 4 0.776314 0.602248 0.768958 11.00000 0.01588 0.01242 = 0.01359 -0.00073 0.00422 -0.00256 N2 4 0.802222 0.577290 0.589085 11.00000 0.01624 0.01020 = 0.01232 -0.00133 0.00315 -0.00175 C1 1 0.754435 0.391296 0.724081 11.00000 0.02580 0.01187 = 0.01492 -0.00079 0.00810 -0.00019 AFIX 23 H1A 2 0.666366 0.300535 0.749181 11.00000 -1.20000 H1B 2 0.870892 0.312654 0.731847 11.00000 -1.20000 AFIX 0 C2 1 0.689615 0.424764 0.628811 11.00000 0.02550 0.01194 = 0.01404 -0.00229 0.00500 -0.00602 AFIX 23 H2A 2 0.688355 0.281887 0.599077 11.00000 -1.20000 H2B 2 0.564666 0.480861 0.621072 11.00000 -1.20000 AFIX 0 C3 1 0.833135 0.784337 0.636072 11.00000 0.01612 0.01295 = 0.01592 0.00008 0.00164 -0.00204 AFIX 23 H3A 2 0.719803 0.869390 0.629414 11.00000 -1.20000 H3B 2 0.923829 0.871335 0.611219 11.00000 -1.20000 AFIX 0 C4 1 0.898516 0.745879 0.731184 11.00000 0.01413 0.01786 = 0.01463 0.00010 0.00441 -0.00366 AFIX 23 H4A 2 1.019905 0.679267 0.738344 11.00000 -1.20000 H4B 2 0.907757 0.887866 0.761819 11.00000 -1.20000 AFIX 0 C5 1 0.768761 0.591846 0.498299 11.00000 0.01010 0.01784 = 0.01362 0.00415 0.00102 0.00180 C6 1 0.819961 0.775338 0.454824 11.00000 0.01940 0.01905 = 0.01786 0.00197 0.00298 -0.00204 AFIX 43 H6 2 0.874536 0.895931 0.486795 11.00000 -1.20000 AFIX 0 C7 1 0.792229 0.784015 0.365533 11.00000 0.02177 0.02226 = 0.02020 0.00745 0.00658 -0.00083 AFIX 43 H7 2 0.828030 0.910876 0.337573 11.00000 -1.20000 AFIX 0 C8 1 0.713443 0.611584 0.316311 11.00000 0.01670 0.03074 = 0.01339 0.00192 0.00134 0.00420 AFIX 43 H8 2 0.694672 0.618576 0.255269 11.00000 -1.20000 AFIX 0 C9 1 0.663335 0.430068 0.358716 11.00000 0.02574 0.02723 = 0.01666 -0.00379 0.00101 -0.00651 AFIX 43 H9 2 0.610006 0.309579 0.326239 11.00000 -1.20000 AFIX 0 C10 1 0.688921 0.419035 0.447796 11.00000 0.02639 0.02161 = 0.01662 0.00124 0.00087 -0.00737 AFIX 43 H10 2 0.651625 0.291940 0.475097 11.00000 -1.20000 AFIX 0 C11 1 0.666807 0.689445 0.821222 11.00000 0.01464 0.01550 = 0.01297 0.00071 0.00009 0.00202 C12 1 0.533820 0.544361 0.856048 11.00000 0.01539 0.01511 = 0.00971 -0.00186 0.00068 -0.00014 C13 1 0.576997 0.339467 0.892050 11.00000 0.01267 0.01433 = 0.01146 -0.00188 0.00174 0.00263 AFIX 43 H13 2 0.696220 0.285267 0.894978 11.00000 -1.20000 AFIX 0 C14 1 0.447636 0.213170 0.923785 11.00000 0.01730 0.01317 = 0.00954 -0.00140 0.00101 0.00114 AFIX 43 H14 2 0.477362 0.073859 0.948719 11.00000 -1.20000 AFIX 0 C15 1 0.274769 0.295155 0.918185 11.00000 0.01350 0.01744 = 0.01100 -0.00151 0.00346 -0.00324 C16 1 0.229031 0.501415 0.886678 11.00000 0.01223 0.01856 = 0.01378 0.00074 0.00291 0.00287 AFIX 43 H16 2 0.110701 0.556801 0.885896 11.00000 -1.20000 AFIX 0 C17 1 0.361040 0.626664 0.855978 11.00000 0.01936 0.01448 = 0.01169 0.00136 0.00115 0.00305 AFIX 43 H17 2 0.332668 0.769940 0.834754 11.00000 -1.20000 AFIX 0 HKLF 5 REM m22123 : space group P21 REM wR2 = 0.0491, GooF = S = 1.044, Restrained GooF = 1.044 for all data REM R1 = 0.0225 for 6410 Fo > 4sig(Fo) and 0.0266 for all 6918 data REM 191 parameters refined using 1 restraints END WGHT 0.0158 0.0999 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.293, deepest hole -0.222, 1-sigma level 0.049 Q1 1 0.1390 -0.0269 0.9380 11.00000 0.05 0.29 Q2 1 0.6041 0.6124 0.8388 11.00000 0.05 0.27 Q3 1 0.7235 0.5098 0.3416 11.00000 0.05 0.22 Q4 1 0.7084 0.7148 0.3439 11.00000 0.05 0.21 Q5 1 0.5638 0.4513 0.8830 11.00000 0.05 0.21 Q6 1 0.7394 0.5081 0.4758 11.00000 0.05 0.20 Q7 1 0.7635 0.7897 0.4173 11.00000 0.05 0.20 Q8 1 0.0375 0.1153 0.8972 11.00000 0.05 0.20 Q9 1 0.2788 0.7591 0.8041 11.00000 0.05 0.19 Q10 1 0.8638 0.7550 0.6790 11.00000 0.05 0.19 Q11 1 0.7749 0.5968 0.5408 11.00000 0.05 0.19 Q12 1 0.7313 0.4062 0.4067 11.00000 0.05 0.19 Q13 1 0.7540 0.6969 0.4749 11.00000 0.05 0.18 Q14 1 0.7367 0.5120 0.6124 11.00000 0.05 0.18 Q15 1 0.0452 0.2555 0.9646 11.00000 0.05 0.18 Q16 1 0.8541 0.7536 0.4170 11.00000 0.05 0.18 Q17 1 0.7438 0.6306 0.8084 11.00000 0.05 0.17 Q18 1 0.4961 0.2518 0.8857 11.00000 0.05 0.17 Q19 1 0.8468 0.5968 0.7734 11.00000 0.05 0.17 Q20 1 0.6220 0.2926 0.8769 11.00000 0.05 0.17 ; _shelx_res_checksum 39843 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br Br1 0.09055(3) 0.11286(6) 0.95039(2) 0.01878(8) Uani d 1 . . O O1 0.6730(3) 0.8844(4) 0.83992(15) 0.0238(5) Uani d 1 . . N N1 0.7763(3) 0.6022(7) 0.76896(13) 0.0138(4) Uani d 1 . . N N2 0.8022(3) 0.5773(4) 0.58908(14) 0.0128(6) Uani d 1 . . C C1 0.7544(4) 0.3913(5) 0.72408(19) 0.0170(6) Uani d 1 . . H H1A 0.666366 0.300535 0.749181 0.020 Uiso calc 1 . . H H1B 0.870892 0.312654 0.731847 0.020 Uiso calc 1 . . C C2 0.6896(4) 0.4248(5) 0.62881(19) 0.0170(6) Uani d 1 . . H H2A 0.688355 0.281887 0.599077 0.020 Uiso calc 1 . . H H2B 0.564666 0.480861 0.621072 0.020 Uiso calc 1 . . C C3 0.8331(4) 0.7843(5) 0.63607(18) 0.0151(6) Uani d 1 . . H H3A 0.719803 0.869390 0.629414 0.018 Uiso calc 1 . . H H3B 0.923829 0.871335 0.611219 0.018 Uiso calc 1 . . C C4 0.8985(4) 0.7459(5) 0.73118(19) 0.0153(6) Uani d 1 . . H H4A 1.019905 0.679267 0.738344 0.018 Uiso calc 1 . . H H4B 0.907757 0.887866 0.761819 0.018 Uiso calc 1 . . C C5 0.7688(3) 0.5918(7) 0.49830(16) 0.0139(6) Uani d 1 . . C C6 0.8200(4) 0.7753(5) 0.4548(2) 0.0187(6) Uani d 1 . . H H6 0.874536 0.895931 0.486795 0.022 Uiso calc 1 . . C C7 0.7922(5) 0.7840(5) 0.3655(2) 0.0211(7) Uani d 1 . . H H7 0.828030 0.910876 0.337573 0.025 Uiso calc 1 . . C C8 0.7134(3) 0.6116(10) 0.31631(16) 0.0204(5) Uani d 1 . . H H8 0.694672 0.618576 0.255269 0.024 Uiso calc 1 . . C C9 0.6633(5) 0.4301(6) 0.3587(2) 0.0234(7) Uani d 1 . . H H9 0.610006 0.309579 0.326239 0.028 Uiso calc 1 . . C C10 0.6889(5) 0.4190(5) 0.4478(2) 0.0218(7) Uani d 1 . . H H10 0.651625 0.291940 0.475097 0.026 Uiso calc 1 . . C C11 0.6668(4) 0.6894(5) 0.82122(18) 0.0146(6) Uani d 1 . . C C12 0.5338(4) 0.5444(4) 0.85605(17) 0.0135(6) Uani d 1 . . C C13 0.5770(4) 0.3395(5) 0.89205(18) 0.0128(6) Uani d 1 . . H H13 0.696220 0.285267 0.894978 0.015 Uiso calc 1 . . C C14 0.4476(4) 0.2132(5) 0.92378(17) 0.0134(6) Uani d 1 . . H H14 0.477362 0.073859 0.948719 0.016 Uiso calc 1 . . C C15 0.2748(4) 0.2952(5) 0.91818(18) 0.0138(6) Uani d 1 . . C C16 0.2290(4) 0.5014(5) 0.88668(18) 0.0148(6) Uani d 1 . . H H16 0.110701 0.556801 0.885896 0.018 Uiso calc 1 . . C C17 0.3610(3) 0.6267(8) 0.85598(15) 0.0153(5) Uani d 1 . . H H17 0.332668 0.769940 0.834754 0.018 Uiso calc 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br1 0.01541(13) 0.01942(13) 0.02254(13) -0.0012(2) 0.00626(9) 0.00283(19) O1 0.0269(12) 0.0140(11) 0.0336(13) -0.0023(9) 0.0145(11) -0.0065(9) N1 0.0159(10) 0.0124(10) 0.0136(9) -0.0026(16) 0.0042(8) -0.0007(16) N2 0.0162(11) 0.0102(17) 0.0123(10) -0.0017(9) 0.0032(8) -0.0013(10) C1 0.0258(17) 0.0119(14) 0.0149(15) -0.0002(12) 0.0081(13) -0.0008(12) C2 0.0255(17) 0.0119(14) 0.0140(15) -0.0060(12) 0.0050(12) -0.0023(11) C3 0.0161(16) 0.0129(14) 0.0159(15) -0.0020(11) 0.0016(12) 0.0001(12) C4 0.0141(15) 0.0179(15) 0.0146(14) -0.0037(11) 0.0044(12) 0.0001(11) C5 0.0101(11) 0.0178(17) 0.0136(11) 0.0018(15) 0.0010(9) 0.0042(15) C6 0.0194(17) 0.0190(16) 0.0179(16) -0.0020(13) 0.0030(13) 0.0020(12) C7 0.0218(18) 0.0223(17) 0.0202(16) -0.0008(13) 0.0066(13) 0.0074(13) C8 0.0167(12) 0.0307(14) 0.0134(11) 0.004(2) 0.0013(9) 0.002(2) C9 0.0257(19) 0.0272(18) 0.0167(16) -0.0065(14) 0.0010(13) -0.0038(13) C10 0.0264(19) 0.0216(17) 0.0166(16) -0.0074(13) 0.0009(13) 0.0012(13) C11 0.0146(14) 0.0155(13) 0.0130(13) 0.0020(10) 0.0001(11) 0.0007(10) C12 0.0154(14) 0.0151(15) 0.0097(13) -0.0001(10) 0.0007(11) -0.0019(9) C13 0.0127(14) 0.0143(14) 0.0115(13) 0.0026(11) 0.0017(11) -0.0019(11) C14 0.0173(15) 0.0132(14) 0.0095(13) 0.0011(11) 0.0010(11) -0.0014(11) C15 0.0135(14) 0.0174(15) 0.0110(14) -0.0032(11) 0.0035(11) -0.0015(11) C16 0.0122(14) 0.0186(15) 0.0138(14) 0.0029(11) 0.0029(11) 0.0007(12) C17 0.0194(12) 0.0145(14) 0.0117(11) 0.0030(19) 0.0012(9) 0.0014(16) 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C11 N1 C4 . . 119.1(3) ? C11 N1 C1 . . 127.0(3) ? C4 N1 C1 . . 111.4(2) ? C5 N2 C2 . . 116.4(2) ? C5 N2 C3 . . 116.4(3) ? C2 N2 C3 . . 113.2(2) ? N1 C1 C2 . . 110.6(2) ? N1 C1 H1A . . 109.5 ? C2 C1 H1A . . 109.5 ? N1 C1 H1B . . 109.5 ? C2 C1 H1B . . 109.5 ? H1A C1 H1B . . 108.1 ? N2 C2 C1 . . 112.8(2) ? N2 C2 H2A . . 109.0 ? C1 C2 H2A . . 109.0 ? N2 C2 H2B . . 109.0 ? C1 C2 H2B . . 109.0 ? H2A C2 H2B . . 107.8 ? N2 C3 C4 . . 111.4(2) ? N2 C3 H3A . . 109.3 ? C4 C3 H3A . . 109.3 ? N2 C3 H3B . . 109.3 ? C4 C3 H3B . . 109.3 ? H3A C3 H3B . . 108.0 ? N1 C4 C3 . . 111.3(2) ? N1 C4 H4A . . 109.4 ? C3 C4 H4A . . 109.4 ? N1 C4 H4B . . 109.4 ? C3 C4 H4B . . 109.4 ? H4A C4 H4B . . 108.0 ? C6 C5 C10 . . 117.0(2) ? C6 C5 N2 . . 121.6(3) ? C10 C5 N2 . . 121.4(3) ? C7 C6 C5 . . 121.0(3) ? C7 C6 H6 . . 119.5 ? C5 C6 H6 . . 119.5 ? C8 C7 C6 . . 121.5(3) ? C8 C7 H7 . . 119.3 ? C6 C7 H7 . . 119.3 ? C9 C8 C7 . . 117.9(2) ? C9 C8 H8 . . 121.1 ? C7 C8 H8 . . 121.1 ? C8 C9 C10 . . 121.5(3) ? C8 C9 H9 . . 119.3 ? C10 C9 H9 . . 119.3 ? C9 C10 C5 . . 121.2(3) ? C9 C10 H10 . . 119.4 ? C5 C10 H10 . . 119.4 ? O1 C11 N1 . . 121.5(3) ? O1 C11 C12 . . 119.4(3) ? N1 C11 C12 . . 119.1(3) ? C17 C12 C13 . . 119.1(3) ? C17 C12 C11 . . 117.3(3) ? C13 C12 C11 . . 123.6(3) ? C14 C13 C12 . . 120.8(3) ? C14 C13 H13 . . 119.6 ? C12 C13 H13 . . 119.6 ? C15 C14 C13 . . 118.5(3) ? C15 C14 H14 . . 120.8 ? C13 C14 H14 . . 120.8 ? C16 C15 C14 . . 122.4(3) ? C16 C15 Br1 . . 118.6(2) ? C14 C15 Br1 . . 119.0(2) ? C15 C16 C17 . . 118.3(3) ? C15 C16 H16 . . 120.9 ? C17 C16 H16 . . 120.9 ? C12 C17 C16 . . 120.9(4) ? C12 C17 H17 . . 119.6 ? C16 C17 H17 . . 119.6 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Br1 C15 . 1.904(3) ? O1 C11 . 1.227(4) ? N1 C11 . 1.356(4) ? N1 C4 . 1.460(4) ? N1 C1 . 1.467(4) ? N2 C5 . 1.415(3) ? N2 C2 . 1.461(4) ? N2 C3 . 1.466(4) ? C1 C2 . 1.518(4) ? C1 H1A . 0.9900 ? C1 H1B . 0.9900 ? C2 H2A . 0.9900 ? C2 H2B . 0.9900 ? C3 C4 . 1.521(4) ? C3 H3A . 0.9900 ? C3 H3B . 0.9900 ? C4 H4A . 0.9900 ? C4 H4B . 0.9900 ? C5 C6 . 1.397(5) ? C5 C10 . 1.401(5) ? C6 C7 . 1.389(4) ? C6 H6 . 0.9500 ? C7 C8 . 1.387(6) ? C7 H7 . 0.9500 ? C8 C9 . 1.376(6) ? C8 H8 . 0.9500 ? C9 C10 . 1.387(4) ? C9 H9 . 0.9500 ? C10 H10 . 0.9500 ? C11 C12 . 1.500(4) ? C12 C17 . 1.393(4) ? C12 C13 . 1.393(4) ? C13 C14 . 1.391(4) ? C13 H13 . 0.9500 ? C14 C15 . 1.383(4) ? C14 H14 . 0.9500 ? C15 C16 . 1.379(4) ? C16 C17 . 1.395(5) ? C16 H16 . 0.9500 ? C17 H17 . 0.9500 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C13 H13 O1 1_545 0.95 2.60 3.018(4) 107.3 no C14 H14 O1 1_545 0.95 2.68 3.052(4) 104.0 no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C11 N1 C1 C2 . . . . 105.4(3) ? C4 N1 C1 C2 . . . . -56.4(3) ? C5 N2 C2 C1 . . . . 170.4(3) ? C3 N2 C2 C1 . . . . -50.7(3) ? N1 C1 C2 N2 . . . . 52.8(3) ? C5 N2 C3 C4 . . . . -170.3(2) ? C2 N2 C3 C4 . . . . 50.8(3) ? C11 N1 C4 C3 . . . . -105.9(3) ? C1 N1 C4 C3 . . . . 57.5(3) ? N2 C3 C4 N1 . . . . -54.1(3) ? C2 N2 C5 C6 . . . . 158.2(3) ? C3 N2 C5 C6 . . . . 20.7(4) ? C2 N2 C5 C10 . . . . -24.3(4) ? C3 N2 C5 C10 . . . . -161.8(3) ? C10 C5 C6 C7 . . . . 0.0(5) ? N2 C5 C6 C7 . . . . 177.6(3) ? C5 C6 C7 C8 . . . . -0.2(5) ? C6 C7 C8 C9 . . . . -0.1(5) ? C7 C8 C9 C10 . . . . 0.5(5) ? C8 C9 C10 C5 . . . . -0.7(5) ? C6 C5 C10 C9 . . . . 0.4(5) ? N2 C5 C10 C9 . . . . -177.2(3) ? C4 N1 C11 O1 . . . . -2.8(4) ? C1 N1 C11 O1 . . . . -163.3(3) ? C4 N1 C11 C12 . . . . 176.5(2) ? C1 N1 C11 C12 . . . . 16.0(4) ? O1 C11 C12 C17 . . . . 42.2(4) ? N1 C11 C12 C17 . . . . -137.1(3) ? O1 C11 C12 C13 . . . . -134.3(3) ? N1 C11 C12 C13 . . . . 46.4(4) ? C17 C12 C13 C14 . . . . 3.2(4) ? C11 C12 C13 C14 . . . . 179.6(3) ? C12 C13 C14 C15 . . . . 0.5(4) ? C13 C14 C15 C16 . . . . -3.6(4) ? C13 C14 C15 Br1 . . . . 173.6(2) ? C14 C15 C16 C17 . . . . 2.9(4) ? Br1 C15 C16 C17 . . . . -174.3(2) ? C13 C12 C17 C16 . . . . -3.8(4) ? C11 C12 C17 C16 . . . . 179.5(3) ? C15 C16 C17 C12 . . . . 0.9(4) ? _cod_database_fobs_code 2244179