#------------------------------------------------------------------------------ #$Date: 2021-07-06 09:40:08 +0300 (Tue, 06 Jul 2021) $ #$Revision: 267275 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/02/23/2022373.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_2022373 loop_ _publ_author_name 'Roy, Monalisa' 'Li, Keyao' 'Nisar, Madiha' 'Wong, Lawrence W.-Y.' 'Sung, Herman H.-Y.' 'Haynes, Richard K.' 'Williams, Ian D.' _publ_section_title ; Varying degrees of homostructurality in a series of cocrystals of antimalarial drug 11-azaartemisinin with salicylic acids ; _journal_coeditor_code DV3004 _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 262 _journal_page_last 270 _journal_paper_doi 10.1107/S2053229621004460 _journal_volume 77 _journal_year 2021 _chemical_absolute_configuration rmad _chemical_formula_iupac 'C15 H23 N O4, C7 H5 Br O3' _chemical_formula_moiety 'C15 H23 N O4, C7 H5 Br O3' _chemical_formula_sum 'C22 H28 Br N O7' _chemical_formula_weight 498.36 _chemical_name_common ; 11-Azaartemisinin--5-bromosalicylic acid (1/1) ; _chemical_name_systematic '1,5,9-Trimethyl-14,15,16-trioxa-11-azatetracyclo[10.3.1.0^4,13^.0^8,13^]hexadecan-10-one; 5-bromosalicylic acid' _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 mixed _atom_sites_solution_primary direct _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _cell_angle_alpha 90 _cell_angle_beta 93.844(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.9325(4) _cell_length_b 9.0196(3) _cell_length_c 12.3942(4) _cell_measurement_reflns_used 2387 _cell_measurement_temperature 100.01(10) _cell_measurement_theta_max 71.7170 _cell_measurement_theta_min 3.5470 _cell_volume 1107.86(7) _computing_cell_refinement ; CrysAlis PRO (Rigaku OD, 2020) ; _computing_data_collection ; CrysAlis PRO (Rigaku OD, 2020) ; _computing_data_reduction ; CrysAlis PRO (Rigaku OD, 2020) ; _computing_molecular_graphics ; OLEX2 (Dolomanov et al., 2009) ; _computing_publication_material ; OLEX2 (Dolomanov et al., 2009) ; _computing_structure_refinement ; SHELXL2014 (Sheldrick, 2015) ; _computing_structure_solution ; SHELXS (Sheldrick, 2008) ; _diffrn_ambient_temperature 100.01(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.1788 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measurement_device 'kappa diffractometer' _diffrn_measurement_device_type 'Rigaku OD SuperNova Dual source diffractometer with an Atlas detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0475 _diffrn_reflns_av_unetI/netI 0.0592 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 6416 _diffrn_reflns_theta_full 66.500 _diffrn_reflns_theta_max 72.510 _diffrn_reflns_theta_min 3.574 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_current 0.80 _diffrn_source_power 0.040 _diffrn_source_voltage 50 _exptl_absorpt_coefficient_mu 2.906 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.96066 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysAlis PRO; Rigaku OD, 2020) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.494 _exptl_crystal_description needle _exptl_crystal_F_000 516 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.239 _refine_diff_density_min -0.392 _refine_ls_abs_structure_details ; Flack x determined using 735 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) ; _refine_ls_abs_structure_Flack -0.04(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 295 _refine_ls_number_reflns 3193 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.018 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0336 _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^)+(0.0101P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.0611 _reflns_number_gt 2929 _reflns_number_total 3193 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file dv3004sup1.cif _cod_data_source_block mona16cult _cod_depositor_comments 'Adding full bibliography for 2022370--2022375.cif.' _cod_original_cell_volume 1107.88(6) _cod_database_code 2022373 _cod_database_fobs_code 2022373 _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 0.760 _shelx_estimated_absorpt_t_max 0.944 _shelx_hkl_file ; 0 -10 0 4966.60 1081.28 12 0 -10 0 5441.58 1289.95 5 0 -10 -1 1498.40 857.449 12 0 -10 1 4560.01 1073.46 12 0 -10 1 2558.30 1091.96 5 0 -10 -1 2283.50 1090.83 5 0 -10 2 6503.03 1170.54 12 0 -10 2 5375.53 1181.50 5 0 -10 -2 4974.54 962.786 12 0 -10 -2 3345.50 1081.09 5 0 -10 3 14980.8 1489.23 5 0 -10 3 11434.7 1298.30 8 0 -10 -3 10289.8 1278.24 12 0 -10 -3 13213.5 1462.55 5 0 -10 -4 3976.03 853.841 12 0 -10 4 5286.37 971.256 8 0 -10 -5 3565.96 804.845 12 0 -10 5 2157.35 689.526 8 0 -10 -6 737.682 507.927 12 0 -9 0-1455.89 1364.86 5 0 -9 0-26.0170 722.022 8 0 -9 0-707.956 1016.79 12 0 -9 -1 7438.30 1584.33 5 0 -9 1 5283.49 1333.85 12 0 -9 1 9178.94 1450.44 8 0 -9 -1 4675.63 1281.08 12 0 -9 1 5864.60 1474.98 5 0 -9 2 9051.59 1571.62 12 0 -9 2 8256.77 1641.78 5 0 -9 -2 10370.7 1725.53 5 0 -9 -2 7412.90 1371.25 12 0 -9 2 8172.04 1442.12 8 0 -9 3 803.704 1023.12 5 0 -9 -3 1325.70 889.941 12 0 -9 3 1078.54 865.333 8 0 -9 -3 748.762 984.586 5 0 -9 3 2403.61 1140.20 12 0 -9 -4 4033.03 1169.84 12 0 -9 4 2952.25 983.929 5 0 -9 4 2610.91 1028.52 8 0 -9 -4 4588.29 1181.02 5 0 -9 -5 2712.83 940.449 12 0 -9 5 3754.37 920.743 5 0 -9 5 2633.79 1005.79 8 0 -9 -5 3091.07 982.002 5 0 -9 -6 755.812 753.690 12 0 -9 6 1597.10 907.300 8 0 -9 -7 395.119 641.438 12 0 -9 7 883.985 630.358 8 0 -9 8 2262.55 586.311 8 0 -9 -8 3338.56 739.695 12 0 -8 0 12556.4 1592.41 8 0 -8 0 12676.9 1726.90 12 0 -8 0 12849.0 1954.65 5 0 -8 1 5220.54 1447.12 5 0 -8 -1 9165.42 1594.82 12 0 -8 -1 6055.84 1168.28 8 0 -8 1 7484.50 1486.59 12 0 -8 1 7386.56 1421.94 8 0 -8 -1 6445.11 1463.08 5 0 -8 -2 5249.26 1013.04 8 0 -8 2 6349.24 1455.33 12 0 -8 2 6388.72 1378.38 8 0 -8 -2 2659.21 1150.18 5 0 -8 -2 3803.65 1173.47 12 0 -8 2 3947.13 1327.46 5 0 -8 -3 29455.9 2794.84 12 0 -8 -3 27786.2 2476.56 5 0 -8 3 24294.1 2318.42 5 0 -8 3 31486.0 2586.11 8 0 -8 3 29258.1 2588.25 12 0 -8 -4 7539.04 1482.25 5 0 -8 4 8595.90 1501.33 5 0 -8 4 9126.84 1576.91 8 0 -8 4 9401.97 1174.90 1 0 -8 -4 8435.73 1586.70 12 0 -8 4 10050.3 1755.41 12 0 -8 -5 32731.4 2744.33 12 0 -8 -5 30850.2 2223.73 5 0 -8 5 32424.7 2616.44 8 0 -8 5 33228.6 2331.95 5 0 -8 5 29744.2 1976.44 1 0 -8 6 5760.00 1302.61 8 0 -8 6 4391.30 869.454 1 0 -8 -6 5181.46 1358.95 12 0 -8 7 20362.8 1581.13 1 0 -8 7 22246.2 1996.79 8 0 -8 -7 20007.5 2060.61 12 0 -8 8 10467.3 1104.15 1 0 -8 -8 11144.8 1499.56 12 0 -8 8 12212.1 1336.15 8 0 -8 -9 1165.38 661.266 12 0 -8 9 2134.01 640.138 8 0 -8 9 955.956 438.173 1 0 -8 -10 8571.36 982.583 12 0 -7 0-411.694 666.331 8 0 -7 0 952.982 957.754 12 0 -7 -1 37724.3 3735.30 4 0 -7 1 36849.9 2461.98 8 0 -7 1 38698.1 2697.67 12 0 -7 -1 42173.5 2381.56 8 0 -7 -1 34694.2 2594.44 12 0 -7 2 5055.34 1104.85 8 0 -7 -2 4550.96 843.122 8 0 -7 -2 8687.60 1905.02 4 0 -7 -2 5401.52 1245.73 12 0 -7 2 7120.11 1357.47 12 0 -7 2 6662.07 877.422 1 0 -7 3 25779.7 1729.17 1 0 -7 -3 25550.7 3012.79 4 0 -7 -3 23303.6 2241.82 12 0 -7 3 28725.5 2317.17 8 0 -7 3 27677.2 2376.17 12 0 -7 -3 27956.9 2318.62 6 0 -7 -4 6403.71 1605.04 4 0 -7 -4 4609.19 1196.91 12 0 -7 4 4969.07 1310.86 12 0 -7 -4 5665.95 1235.22 5 0 -7 4 5942.40 1018.95 1 0 -7 4 4255.64 1157.98 8 0 -7 4 4600.31 1199.73 5 0 -7 -4 6715.89 1446.85 6 0 -7 5 42396.2 3047.88 12 0 -7 -5 43168.2 2522.63 5 0 -7 5 46499.2 3013.38 8 0 -7 -5 46428.4 3299.34 6 0 -7 -5 45233.6 3185.96 12 0 -7 5 46026.9 2598.92 1 0 -7 5 43025.7 2543.55 5 0 -7 -6 16488.3 2095.44 6 0 -7 6 13625.0 1540.27 1 0 -7 -6 19618.7 2196.00 12 0 -7 6 17276.9 2003.99 8 0 -7 -7 2653.19 1095.44 12 0 -7 7 2985.30 1055.68 8 0 -7 -7 5042.26 1560.58 6 0 -7 7 5031.96 1076.76 1 0 -7 -8 8807.40 1611.76 12 0 -7 8 10127.7 1415.00 8 0 -7 8 9485.19 1308.14 1 0 -7 9 11373.7 1280.21 8 0 -7 9 12913.2 1395.77 1 0 -7 -9 9152.84 1528.71 12 0 -7 -10 2588.25 895.591 12 0 -7 10 1048.83 611.938 1 0 -7 -11 34.2453 509.520 12 0 -7 11 429.134 401.661 1 0 -6 0 53171.7 4154.05 4 0 -6 1 31254.7 3223.95 4 0 -6 -1 26677.3 2966.09 4 0 -6 -2 4604.98 1485.18 4 0 -6 2 5362.85 987.628 8 0 -6 -3 122157. 4234.99 6 0 -6 -3 127280. 4366.57 12 0 -6 -3 125115. 6170.48 4 0 -6 3 120388. 4119.21 12 0 -6 3 123227. 4105.11 8 0 -6 4 12277.3 1577.19 12 0 -6 4 10703.7 1413.87 8 0 -6 4 12426.6 1288.99 1 0 -6 -4 10182.5 1556.82 6 0 -6 -4 11627.2 2083.63 4 0 -6 -4 11110.6 1538.77 12 0 -6 5 1743.54 705.734 1 0 -6 5 2464.27 1269.28 12 0 -6 -5 1422.44 750.280 12 0 -6 5 3658.71 1084.34 8 0 -6 -5 784.613 966.720 4 0 -6 -5 1651.18 961.789 6 0 -6 -6 11881.0 1303.87 7 0 -6 -6 13334.4 1750.47 12 0 -6 6 12046.0 1466.40 1 0 -6 -6 13645.2 2053.14 4 0 -6 -6 12832.9 1865.21 6 0 -6 6 13183.9 1632.42 8 0 -6 -7 3039.44 1040.78 12 0 -6 7 4699.13 1110.46 8 0 -6 -7 5198.41 998.770 7 0 -6 7 4495.44 1002.47 1 0 -6 -7 5310.09 1376.80 6 0 -6 -8 2500.07 1122.73 6 0 -6 -8 2398.84 1157.95 12 0 -6 8 2003.45 859.643 1 0 -6 -8 1749.57 853.131 7 0 -6 8 2246.48 934.672 8 0 -6 9 5527.23 1143.30 1 0 -6 -9 4803.83 1013.72 7 0 -6 9 6137.69 1042.25 8 0 -6 -9 4843.28 1222.51 6 0 -6 -9 4157.73 1274.82 12 0 -6 -10 4045.52 859.249 7 0 -6 -10 4905.49 1176.53 12 0 -6 10 6070.86 1104.81 1 0 -6 -11 19104.3 1866.79 12 0 -6 -11 17659.3 1315.11 7 0 -6 11 16083.6 1505.80 1 0 -6 -12 3269.65 766.586 12 0 -6 12 2859.87 657.399 1 0 -5 0 142.185 778.009 4 0 -5 1 55475.4 3850.96 4 0 -5 -1 56279.8 3761.09 4 0 -5 -2 84023.5 4618.23 4 0 -5 -3 1380.09 943.211 4 0 -5 -4 10912.7 1856.88 4 0 -5 -5 30412.4 2130.48 6 0 -5 -5 34356.5 3100.18 4 0 -5 -5 29884.9 2108.07 12 0 -5 -6 25136.1 1726.97 7 0 -5 6 27888.3 1948.36 1 0 -5 -6 24576.7 2101.29 12 0 -5 6 27383.8 1908.33 8 0 -5 -6 27721.7 2903.37 4 0 -5 -6 26405.6 2213.85 6 0 -5 7 5799.01 1104.47 1 0 -5 -7 6425.80 1437.38 4 0 -5 -7 5192.11 1045.03 7 0 -5 -7 7942.07 1328.65 6 0 -5 7 7910.60 1210.23 8 0 -5 8-615.587 635.712 8 0 -5 -8-379.703 774.901 7 0 -5 -8 1805.10 1025.75 6 0 -5 8 972.106 820.680 1 0 -5 -9 25687.6 2303.41 6 0 -5 -9 24373.9 2088.74 7 0 -5 9 26707.7 2317.05 1 0 -5 -10 17143.5 1810.33 6 0 -5 10 13694.5 1738.97 1 0 -5 -10 15076.3 2027.73 12 0 -5 -10 14388.1 1683.49 7 0 -5 11 1005.52 820.353 1 0 -5 -11 1822.65 1011.08 12 0 -5 -11 1342.54 738.990 7 0 -5 -12 11454.4 1465.70 12 0 -5 12 14164.8 1507.56 1 0 -5 -12 9719.92 1138.66 7 0 -5 13 11029.3 1052.16 1 0 -5 -13 11396.1 1166.19 12 0 -5 -13 9900.22 800.473 7 0 -4 0 78036.1 3854.50 4 0 -4 -1 7465.21 1361.90 4 0 -4 1 8439.44 1508.77 4 0 -4 -2 11000.3 1632.61 4 0 -4 -3 52542.4 3268.50 4 0 -4 -4 40434.2 3030.87 4 0 -4 -5 23257.3 2410.28 4 0 -4 -6 17797.6 2171.95 4 0 -4 -7 60199.4 2917.91 6 0 -4 -7 68402.6 4263.14 4 0 -4 -8 45386.6 2718.86 6 0 -4 -8 48003.2 3531.50 4 0 -4 9 8237.50 1287.13 11 0 -4 -9 8924.68 1379.19 6 0 -4 -10 28356.8 2142.97 6 0 -4 10 26895.5 2293.99 11 0 -4 -11 12631.6 1659.57 7 0 -4 11 14637.3 1667.48 11 0 -4 -12 2660.46 932.609 7 0 -4 12 3734.24 976.176 11 0 -4 12 2692.39 968.215 1 0 -4 13 6367.50 982.546 1 0 -4 13 5617.62 864.111 11 0 -4 -13 5871.88 909.422 7 0 -4 -13 6964.34 1145.91 12 0 -4 14 17453.6 1137.11 1 0 -4 -14 16007.2 1193.46 12 0 -3 0-38.7443 672.168 4 0 -3 1 17880.0 1672.87 4 0 -3 -1 20908.5 1711.76 4 0 -3 -2 227835. 5525.48 4 0 -3 -3 168743. 4971.44 4 0 -3 -4 38772.2 2601.05 4 0 -3 -5 89404.9 4106.47 4 0 -3 -6 41356.4 2957.72 4 0 -3 -7 11178.1 1742.42 4 0 -3 8 93385.3 3598.15 11 0 -3 -8 92985.6 3216.01 6 0 -3 -8 85006.8 4578.44 4 0 -3 -9 40348.0 3103.54 4 0 -3 9 43162.0 2867.78 11 0 -3 10 7493.52 1477.43 11 0 -3 11 5391.35 1360.53 11 0 -3 12 15030.8 1858.21 11 0 -3 13 21033.4 1906.61 11 0 -3 -13 20665.3 1833.67 7 0 -3 -14 736.513 497.224 7 0 -3 14 715.450 533.550 11 0 -3 14 611.525 530.868 1 0 -2 0 222799. 4120.17 4 0 -2 1 311369. 5109.00 4 0 -2 -1 309361. 4911.94 4 0 -2 -2 137770. 1391.86 2 0 -2 -2 133707. 3454.97 4 0 -2 -3 5090.63 906.056 4 0 -2 -3 4871.10 522.043 2 0 -2 -4 159754. 4524.32 4 0 -2 -4 162028. 3364.91 2 0 -2 -5 53446.1 2901.79 4 0 -2 -5 54739.0 2349.69 2 0 -2 -6 137221. 4236.50 2 0 -2 -6 128478. 4790.24 4 0 -2 -7 44607.1 3063.71 4 0 -2 -7 49891.5 2859.64 2 0 -2 -8 50345.7 3426.17 4 0 -2 9 28939.6 2452.27 11 0 -2 -9 25826.0 2532.36 4 0 -2 10 43767.3 3177.44 11 0 -2 11 45149.2 3396.38 11 0 -2 12 1596.49 1046.86 11 0 -2 13-137.418 899.949 11 0 -2 14 14742.4 1559.75 11 0 -2 -14 14157.8 1373.58 7 0 -2 15 5954.81 625.863 1 0 -2 -15 4639.92 651.081 12 0 -1 0-28.5977 261.701 4 0 -1 -1 1322.18 372.267 4 0 -1 1 1160.68 407.768 4 0 -1 -2 335153. 4755.33 3 0 -1 -3 20668.0 1525.71 3 0 -1 -4 55359.5 2778.17 3 0 -1 -5 732.504 868.913 3 0 -1 -6 335021. 8485.51 3 0 -1 -7 55277.5 3326.39 2 0 -1 -8 26966.9 2575.65 2 0 -1 9 22196.3 2130.23 11 0 -1 -9 21499.8 2432.65 2 0 -1 -10 22680.1 2413.33 2 0 -1 10 25189.7 2515.40 11 0 -1 11 9410.01 1872.49 11 0 -1 12 18668.2 2352.82 11 0 -1 13 12687.6 1867.41 11 0 -1 14 2105.33 832.849 11 0 -1 15 6364.27 678.032 1 0 -1 -15 4694.04 725.128 7 0 -1 15 4744.65 763.289 11 0 0 -1 13524.1 565.643 3 0 0 -2 159608. 2830.96 3 0 0 -3 19478.1 1364.87 3 0 0 -4 279381. 5588.23 3 0 0 -5 26924.4 2080.01 3 0 0 -6 194205. 6058.46 3 0 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9735.34 1182.87 6 -10 2 -7 240.194 551.576 6 -10 3 4 1896.46 806.362 11 -10 3 3 25752.8 2105.57 11 -10 3 2 4554.86 1150.20 11 -10 3 1 9909.78 1444.59 11 -10 3 0 11229.2 1550.23 11 -10 3 -6 2082.47 678.242 6 -11 -4 3 8103.56 1046.23 10 11 -4 -3 10309.8 948.719 9 11 -4 -2 5285.40 834.433 9 -11 -4 2 5337.85 1009.55 10 11 -4 -1 7756.51 959.464 9 -11 -4 1 5892.70 1037.19 10 11 -4 0 7651.46 959.497 9 -11 -4 0 8870.19 1206.79 10 11 -4 1 8620.72 993.623 9 -11 -4 -1 8125.22 1078.02 10 11 -4 2 360.238 450.171 9 -11 -4 -2 721.367 510.243 10 -11 -3 5 4815.89 812.247 11 11 -3 -4 3642.56 625.952 9 -11 -3 4 2666.96 787.448 11 -11 -3 4 4349.01 892.455 10 11 -3 -3 179.045 457.757 9 -11 -3 3-833.433 658.359 11 -11 -3 3 964.562 841.726 10 11 -3 -2 1018.47 600.090 9 -11 -3 2 995.907 689.521 11 -11 -3 2 1150.10 876.728 10 11 -3 -1 4732.63 869.827 9 -11 -3 1 2620.42 879.772 11 -11 -3 1 3782.52 1050.91 10 11 -3 0 1110.42 659.949 9 -11 -3 0 1366.80 820.224 11 -11 -3 0 1083.97 814.172 10 11 -3 1 7827.23 1035.31 9 -11 -3 -1 7447.46 1175.13 10 11 -3 2 2673.79 709.955 9 -11 -3 -2 1416.25 735.675 10 -11 -3 -3 10591.8 938.807 10 11 -3 3 6090.62 802.399 9 -11 -2 7 3328.25 696.535 11 -11 -2 6 3381.84 803.666 11 -11 -2 5 1327.67 712.414 11 -11 -2 5 96.4147 525.346 10 -11 -2 4 11320.9 1494.41 11 -11 -2 4 12781.6 1440.66 10 -11 -2 3 1169.93 898.433 11 -11 -2 2 1484.06 990.114 11 11 -2 -1 3607.80 721.379 9 -11 -2 1 3854.73 1209.50 11 11 -2 0 6353.29 890.290 9 -11 -2 0 6038.49 1382.20 11 11 -2 1 2967.79 715.246 9 -11 -2 -1 3589.30 1067.51 11 11 -2 2 2438.46 749.998 9 -11 -2 -2 1775.47 889.072 10 -11 -2 -3 2802.05 682.535 10 11 -2 3 2505.74 607.227 9 -11 -2 -4 11979.0 880.361 6 11 -2 4 15312.0 1037.72 9 -11 -1 7 1199.23 687.622 11 -11 -1 6 6923.17 1166.70 11 -11 -1 5 7200.20 1299.67 11 -11 -1 4 8915.66 1483.74 11 -11 -1 3 1483.92 1045.57 11 -11 -1 2 10674.9 1720.94 11 -11 -1 1 18514.9 2175.80 11 -11 -1 0-68.5046 1112.10 11 -11 -1 -1 7374.36 1516.04 11 -11 -1 -2 4459.58 775.763 6 -11 -1 -3 3185.67 645.121 6 -11 -1 -4 1273.62 540.795 6 -11 -1 -5 6603.55 765.567 6 -11 0 7 21169.3 1643.48 11 -11 0 6 1701.09 824.912 11 -11 0 5-16.9421 792.339 11 -11 0 4 6197.34 1416.39 11 -11 0 3 7232.99 1536.97 11 -11 0 2 3170.45 1248.30 11 -11 0 1 1988.08 1089.21 11 -11 0 0 4908.66 1370.51 11 -11 0 -1 3713.54 1229.60 11 -11 0 -1 565.622 483.323 6 -11 0 -2 82.9692 582.259 6 -11 0 -3 9401.24 1087.25 6 -11 0 -4 1170.44 618.922 6 -11 0 -5 1433.16 553.783 6 -11 1 7-585.389 571.907 11 -11 1 6 6778.96 1081.72 11 -11 1 5 8956.65 1365.27 11 -11 1 4 8974.37 1436.79 11 -11 1 3 4558.14 1271.34 11 -11 1 2 11239.0 1706.55 11 -11 1 1 20015.6 2141.67 11 -11 1 0 1039.53 993.838 11 -11 1 -1 6806.91 1451.85 11 -11 1 -2 4908.00 897.479 6 -11 1 -3 2977.66 725.395 6 -11 1 -4 784.913 588.526 6 -11 1 -5 7591.72 881.401 6 -11 2 6 1477.31 524.530 11 -11 2 5 1582.12 602.836 11 -11 2 4 12192.9 1438.84 11 -11 2 3 3120.58 1010.99 11 -11 2 2 2303.21 959.657 11 -11 2 1 2126.43 869.697 11 -11 2 0 6094.61 1235.90 11 -11 2 -4 15986.0 1267.22 6 -11 2 -5 1828.66 547.901 6 -11 3 -4 1091.95 540.113 6 -12 -2 2 3792.23 733.774 11 -12 -2 2 1679.10 620.485 10 -12 -2 1 2327.93 664.245 10 -12 -2 0 311.519 528.291 10 -12 -1 4 4872.19 811.214 11 -12 -1 3 553.337 574.082 11 -12 -1 3 1181.18 587.602 10 -12 -1 2 2917.73 783.940 11 -12 -1 1 1380.37 739.193 11 -12 -1 -1 331.816 517.207 10 -12 0 4 2008.10 673.883 11 -12 0 3 1905.04 695.482 11 -12 0 2 5986.68 1014.32 11 -12 0 1 5793.11 1032.09 11 -12 1 3 480.677 523.914 11 -12 1 2 3609.58 771.655 11 -12 1 1 1187.39 653.908 11 0 0 0 0.00 0.00 0 TITL mona16CuLT in P2(1) REM P2(1) (#4 in standard setting) CELL 1.54184 9.932532 9.019645 12.394226 90.0000 93.8440 90.0000 ZERR 5.00 0.000346 0.000284 0.000374 0.0000 0.0029 0.0000 LATT -1 SYMM -x, y+1/2,-z SFAC C H N O UNIT 55.00 50.00 5.00 5.00 TREF HKLF 4 END ; _shelx_hkl_checksum 52793 _shelx_res_file ; mona16cult.res created by SHELXL-2014/7 TITL Mono16CuLT in P21 100K CELL 1.54184 9.93253 9.01965 12.39423 90 93.844 90 ZERR 2 0.00035 0.00028 0.00037 0 0.0029 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H Br N O UNIT 44 56 2 2 14 L.S. 20 PLAN 20 SIZE 0.02 0.02 0.1 TEMP -173 HTAB N11 O21 HTAB O22 O21 HTAB O20 O10 HTAB CONF fmap 2 acta 133 MERG 2 REM REM REM WGHT 0.010100 FVAR 7.01691 O1 5 0.553170 0.703415 0.665610 11.00000 0.02278 0.01796 = 0.02685 -0.00117 0.00171 0.00304 C1 1 0.602968 0.551391 0.663965 11.00000 0.01945 0.01648 = 0.02580 -0.00175 -0.00014 0.00049 O2 5 0.412327 0.715416 0.622104 11.00000 0.02276 0.02436 = 0.02825 0.00593 0.00325 0.00184 C2 1 0.506464 0.457857 0.591117 11.00000 0.02233 0.02010 = 0.02333 -0.00136 0.00065 0.00364 AFIX 13 H2 2 0.536815 0.352360 0.597899 11.00000 -1.20000 AFIX 0 O3 5 0.370942 0.463817 0.618998 11.00000 0.02302 0.02311 = 0.02652 0.00338 0.00198 -0.00415 C3 1 0.337375 0.601584 0.668566 11.00000 0.02784 0.02487 = 0.02703 0.00371 0.00903 0.00522 C4 1 0.365819 0.594256 0.791284 11.00000 0.03506 0.03540 = 0.02585 0.00262 0.00884 0.00020 AFIX 23 H4A 2 0.280950 0.569217 0.824715 11.00000 -1.20000 H4B 2 0.394560 0.693638 0.817756 11.00000 -1.20000 AFIX 0 C5 1 0.474397 0.480918 0.829143 11.00000 0.03983 0.03048 = 0.02388 0.00752 0.00055 -0.00197 AFIX 23 H5A 2 0.488316 0.487906 0.908823 11.00000 -1.20000 H5B 2 0.438923 0.380494 0.811917 11.00000 -1.20000 AFIX 0 C6 1 0.691377 0.348968 0.794521 11.00000 0.03559 0.02145 = 0.03236 0.00067 -0.00703 0.00053 AFIX 13 H6 2 0.637218 0.271074 0.753913 11.00000 -1.20000 AFIX 0 C7 1 0.826035 0.360247 0.743527 11.00000 0.03071 0.02643 = 0.05266 0.00215 -0.01444 0.00589 AFIX 23 H7A 2 0.870851 0.262173 0.747398 11.00000 -1.20000 H7B 2 0.884573 0.431141 0.785757 11.00000 -1.20000 AFIX 0 C8 1 0.812041 0.410670 0.626107 11.00000 0.02007 0.02892 = 0.04652 -0.00757 -0.00618 0.00389 AFIX 23 H8A 2 0.759686 0.336267 0.582111 11.00000 -1.20000 H8B 2 0.902572 0.418847 0.597732 11.00000 -1.20000 AFIX 0 C9 1 0.726933 0.630487 0.503062 11.00000 0.02079 0.02539 = 0.02286 -0.00850 0.00097 -0.00229 AFIX 13 H9 2 0.703152 0.736828 0.514406 11.00000 -1.20000 AFIX 0 O10 5 0.606945 0.587910 0.331814 11.00000 0.02499 0.02831 = 0.02201 -0.00241 0.00037 -0.00601 C10 1 0.611395 0.567681 0.432092 11.00000 0.02125 0.01545 = 0.02748 -0.00682 0.00304 0.00039 N11 4 0.511075 0.500269 0.478213 11.00000 0.02258 0.01901 = 0.02534 -0.00208 0.00071 -0.00278 C11 1 0.612064 0.495675 0.781508 11.00000 0.03104 0.01930 = 0.02388 -0.00065 -0.00678 -0.00049 AFIX 13 H11A 2 0.664052 0.571772 0.825714 11.00000 -1.20000 AFIX 0 C12 1 0.740193 0.561739 0.616775 11.00000 0.02352 0.02131 = 0.02874 -0.00412 -0.00407 0.00122 AFIX 13 H12 2 0.795395 0.632254 0.663652 11.00000 -1.20000 AFIX 0 C13 1 0.191783 0.634114 0.632044 11.00000 0.02305 0.04513 = 0.03925 0.01285 0.00865 0.00581 AFIX 137 H13A 2 0.163851 0.727144 0.664744 11.00000 -1.50000 H13B 2 0.134256 0.553112 0.654671 11.00000 -1.50000 H13C 2 0.183046 0.643131 0.553089 11.00000 -1.50000 AFIX 0 C14 1 0.707965 0.299484 0.912401 11.00000 0.05886 0.03332 = 0.03906 0.00882 -0.01964 0.00185 AFIX 137 H14A 2 0.752098 0.378335 0.956173 11.00000 -1.50000 H14B 2 0.763395 0.209575 0.917952 11.00000 -1.50000 H14C 2 0.619056 0.278763 0.938781 11.00000 -1.50000 AFIX 0 C15 1 0.858558 0.633689 0.445703 11.00000 0.02178 0.05558 = 0.03399 -0.00391 0.00302 -0.00889 AFIX 137 H15A 2 0.880815 0.533123 0.422833 11.00000 -1.50000 H15B 2 0.931464 0.671633 0.495351 11.00000 -1.50000 H15C 2 0.847720 0.698364 0.382179 11.00000 -1.50000 AFIX 0 BR5 3 0.229692 0.152271 -0.140144 11.00000 0.03676 0.05062 = 0.02552 -0.01035 0.00600 -0.00966 O20 5 0.436452 0.476726 0.192641 11.00000 0.02197 0.02623 = 0.02390 0.00318 0.00297 -0.00611 C20 1 0.316400 0.454947 0.228173 11.00000 0.02508 0.01817 = 0.02749 0.00693 -0.00433 -0.00078 O21 5 0.283302 0.498798 0.316870 11.00000 0.02444 0.02792 = 0.02300 -0.00246 0.00253 0.00071 C21 1 0.220926 0.372105 0.153461 11.00000 0.01992 0.02433 = 0.02075 0.00518 0.00103 0.00096 O22 5 0.044733 0.391052 0.278718 11.00000 0.02330 0.04282 = 0.02768 -0.00284 0.00327 0.00098 C22 1 0.090126 0.342648 0.184603 11.00000 0.02055 0.03139 = 0.02401 0.00405 0.00162 0.00362 C23 1 0.002305 0.257272 0.116374 11.00000 0.02161 0.04644 = 0.03193 0.00048 0.00648 -0.00612 AFIX 43 H23 2 -0.087069 0.238850 0.135833 11.00000 -1.20000 AFIX 0 C24 1 0.044480 0.200462 0.022143 11.00000 0.02344 0.05133 = 0.02714 -0.00262 -0.00157 -0.01166 AFIX 43 H24 2 -0.014626 0.140126 -0.022427 11.00000 -1.20000 AFIX 0 C25 1 0.174113 0.230865 -0.008744 11.00000 0.02961 0.03431 = 0.01967 -0.00197 0.00145 -0.00069 C26 1 0.260763 0.316287 0.055319 11.00000 0.02161 0.02925 = 0.02310 0.00366 0.00412 -0.00193 AFIX 43 H26 2 0.348322 0.337730 0.033004 11.00000 -1.20000 AFIX 0 H11 2 0.454194 0.466408 0.426616 11.00000 0.05786 H22 2 0.107271 0.429570 0.313679 11.00000 0.02429 H20 2 0.495388 0.515944 0.240142 11.00000 0.08844 HKLF 4 REM Mono16CuLT in P21 100K REM R1 = 0.0336 for 2929 Fo > 4sig(Fo) and 0.0395 for all 3193 data REM 295 parameters refined using 1 restraints END WGHT 0.0101 0.0000 REM Instructions for potential hydrogen bonds EQIV $1 -x+1, y-1/2, -z+1 HTAB N11 O1_$1 HTAB N11 O21 HTAB O22 O21 HTAB O20 O10 REM Highest difference peak 0.239, deepest hole -0.392, 1-sigma level 0.055 Q1 1 0.7042 0.5522 0.9818 11.00000 0.05 0.24 Q2 1 0.2245 0.3104 -0.1404 11.00000 0.05 0.21 Q3 1 0.7130 0.1552 0.9237 11.00000 0.05 0.21 Q4 1 0.2273 -0.0069 -0.1453 11.00000 0.05 0.20 Q5 1 0.2171 0.1596 -0.0436 11.00000 0.05 0.20 Q6 1 0.0400 0.2144 -0.1389 11.00000 0.05 0.20 Q7 1 0.8379 0.3833 0.6804 11.00000 0.05 0.20 Q8 1 0.4472 0.3510 0.1915 11.00000 0.05 0.20 Q9 1 0.3613 0.6558 0.9427 11.00000 0.05 0.19 Q10 1 0.1142 0.1526 0.0202 11.00000 0.05 0.19 Q11 1 0.2967 0.2525 0.0070 11.00000 0.05 0.18 Q12 1 0.7282 0.6096 0.5630 11.00000 0.05 0.18 Q13 1 0.0125 0.1593 0.0216 11.00000 0.05 0.18 Q14 1 0.5587 0.5510 0.7248 11.00000 0.05 0.18 Q15 1 0.6464 0.5006 0.7065 11.00000 0.05 0.18 Q16 1 0.2654 0.6565 0.6508 11.00000 0.05 0.17 Q17 1 0.2444 0.5850 0.4310 11.00000 0.05 0.17 Q18 1 0.3763 0.8068 0.9007 11.00000 0.05 0.17 Q19 1 0.9225 0.7163 0.5651 11.00000 0.05 0.17 Q20 1 0.1633 0.0888 -0.1633 11.00000 0.05 0.17 ; _shelx_res_checksum 80759 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 O O1 0.5532(3) 0.7034(3) 0.6656(3) 0.0225(7) Uani d 1 . . C C1 0.6030(5) 0.5514(5) 0.6640(4) 0.0207(9) Uani d 1 . . O O2 0.4123(3) 0.7154(3) 0.6221(3) 0.0251(7) Uani d 1 . . C C2 0.5065(4) 0.4579(4) 0.5911(3) 0.0220(9) Uani d 1 . . H H2 0.5368 0.3524 0.5979 0.026 Uiso calc 1 . . O O3 0.3709(3) 0.4638(3) 0.6190(2) 0.0242(7) Uani d 1 . . C C3 0.3374(5) 0.6016(5) 0.6686(4) 0.0263(10) Uani d 1 . . C C4 0.3658(5) 0.5943(5) 0.7913(4) 0.0318(11) Uani d 1 . . H H4A 0.2810 0.5692 0.8247 0.038 Uiso calc 1 . . H H4B 0.3946 0.6936 0.8178 0.038 Uiso calc 1 . . C C5 0.4744(5) 0.4809(5) 0.8291(4) 0.0315(11) Uani d 1 . . H H5A 0.4883 0.4879 0.9088 0.038 Uiso calc 1 . . H H5B 0.4389 0.3805 0.8119 0.038 Uiso calc 1 . . C C6 0.6914(6) 0.3490(5) 0.7945(4) 0.0302(12) Uani d 1 . . H H6 0.6372 0.2711 0.7539 0.036 Uiso calc 1 . . C C7 0.8260(5) 0.3602(5) 0.7435(4) 0.0374(13) Uani d 1 . . H H7A 0.8709 0.2622 0.7474 0.045 Uiso calc 1 . . H H7B 0.8846 0.4311 0.7858 0.045 Uiso calc 1 . . C C8 0.8120(5) 0.4107(5) 0.6261(4) 0.0322(11) Uani d 1 . . H H8A 0.7597 0.3363 0.5821 0.039 Uiso calc 1 . . H H8B 0.9026 0.4188 0.5977 0.039 Uiso calc 1 . . C C9 0.7269(4) 0.6305(5) 0.5031(3) 0.0230(9) Uani d 1 . . H H9 0.7032 0.7368 0.5144 0.028 Uiso calc 1 . . O O10 0.6069(3) 0.5879(3) 0.3318(3) 0.0252(7) Uani d 1 . . C C10 0.6114(4) 0.5677(4) 0.4321(4) 0.0213(9) Uani d 1 . . N N11 0.5111(4) 0.5003(4) 0.4782(3) 0.0224(8) Uani d 1 . . C C11 0.6121(5) 0.4957(5) 0.7815(4) 0.0251(10) Uani d 1 . . H H11A 0.6641 0.5718 0.8257 0.030 Uiso calc 1 . . C C12 0.7402(4) 0.5617(5) 0.6168(4) 0.0248(10) Uani d 1 . . H H12 0.7954 0.6323 0.6637 0.030 Uiso calc 1 . . C C13 0.1918(4) 0.6341(7) 0.6320(4) 0.0355(11) Uani d 1 . . H H13A 0.1639 0.7271 0.6647 0.053 Uiso calc 1 . . H H13B 0.1343 0.5531 0.6547 0.053 Uiso calc 1 . . H H13C 0.1830 0.6431 0.5531 0.053 Uiso calc 1 . . C C14 0.7080(6) 0.2995(6) 0.9124(4) 0.0448(14) Uani d 1 . . H H14A 0.7521 0.3783 0.9562 0.067 Uiso calc 1 . . H H14B 0.7634 0.2096 0.9180 0.067 Uiso calc 1 . . H H14C 0.6191 0.2788 0.9388 0.067 Uiso calc 1 . . C C15 0.8586(4) 0.6337(7) 0.4457(4) 0.0371(12) Uani d 1 . . H H15A 0.8808 0.5331 0.4228 0.056 Uiso calc 1 . . H H15B 0.9315 0.6716 0.4954 0.056 Uiso calc 1 . . H H15C 0.8477 0.6984 0.3822 0.056 Uiso calc 1 . . Br Br5 0.22969(5) 0.15227(6) -0.14014(4) 0.03746(12) Uani d 1 . . O O20 0.4365(3) 0.4767(3) 0.1926(3) 0.0240(7) Uani d 1 . . C C20 0.3164(5) 0.4549(5) 0.2282(4) 0.0239(11) Uani d 1 . . O O21 0.2833(3) 0.4988(3) 0.3169(2) 0.0251(7) Uani d 1 . . C C21 0.2209(4) 0.3721(5) 0.1535(3) 0.0217(9) Uani d 1 . . O O22 0.0447(3) 0.3911(4) 0.2787(3) 0.0312(8) Uani d 1 . . C C22 0.0901(5) 0.3426(5) 0.1846(4) 0.0253(9) Uani d 1 . . C C23 0.0023(5) 0.2573(5) 0.1164(4) 0.0331(12) Uani d 1 . . H H23 -0.0871 0.2388 0.1358 0.040 Uiso calc 1 . . C C24 0.0445(5) 0.2005(6) 0.0221(4) 0.0341(12) Uani d 1 . . H H24 -0.0146 0.1401 -0.0224 0.041 Uiso calc 1 . . C C25 0.1741(5) 0.2309(5) -0.0087(4) 0.0279(10) Uani d 1 . . C C26 0.2608(5) 0.3163(5) 0.0553(3) 0.0245(9) Uani d 1 . . H H26 0.3483 0.3377 0.0330 0.029 Uiso calc 1 . . H H11 0.454(6) 0.466(7) 0.427(5) 0.06(2) Uiso d 1 . . H H22 0.107(5) 0.430(5) 0.314(4) 0.024(14) Uiso d 1 . . H H20 0.495(7) 0.516(8) 0.240(6) 0.09(3) Uiso d 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0228(16) 0.0180(15) 0.0268(17) 0.0030(11) 0.0017(13) -0.0012(11) C1 0.019(2) 0.016(2) 0.026(2) 0.0005(17) -0.0001(18) -0.0018(16) O2 0.0228(16) 0.0244(15) 0.0283(17) 0.0018(13) 0.0033(13) 0.0059(12) C2 0.022(2) 0.020(2) 0.023(2) 0.0036(17) 0.0007(18) -0.0014(16) O3 0.0230(16) 0.0231(16) 0.0265(16) -0.0041(12) 0.0020(13) 0.0034(12) C3 0.028(2) 0.025(2) 0.027(2) 0.0052(17) 0.009(2) 0.0037(17) C4 0.035(3) 0.035(2) 0.026(2) 0.000(2) 0.009(2) 0.0026(18) C5 0.040(3) 0.030(3) 0.024(2) -0.002(2) 0.001(2) 0.008(2) C6 0.036(3) 0.021(2) 0.032(3) 0.001(2) -0.007(2) 0.001(2) C7 0.031(3) 0.026(2) 0.053(3) 0.006(2) -0.014(2) 0.002(2) C8 0.020(2) 0.029(2) 0.047(3) 0.0039(19) -0.006(2) -0.008(2) C9 0.021(2) 0.025(3) 0.0229(18) -0.0023(19) 0.0010(15) -0.0085(19) O10 0.0250(17) 0.0283(15) 0.0220(16) -0.0060(13) 0.0004(13) -0.0024(12) C10 0.021(2) 0.015(2) 0.027(2) 0.0004(17) 0.0030(19) -0.0068(17) N11 0.023(2) 0.0190(17) 0.025(2) -0.0028(15) 0.0007(16) -0.0021(15) C11 0.031(3) 0.019(2) 0.024(2) -0.0005(19) -0.0068(19) -0.0006(17) C12 0.024(2) 0.021(2) 0.029(3) 0.0012(18) -0.0041(19) -0.0041(17) C13 0.023(2) 0.045(3) 0.039(2) 0.006(3) 0.0087(19) 0.013(3) C14 0.059(4) 0.033(3) 0.039(3) 0.002(3) -0.020(3) 0.009(2) C15 0.022(2) 0.056(3) 0.034(2) -0.009(3) 0.0030(18) -0.004(3) Br5 0.0368(3) 0.0506(3) 0.0255(2) -0.0097(3) 0.00600(18) -0.0104(3) O20 0.0220(17) 0.0262(16) 0.0239(16) -0.0061(13) 0.0030(13) 0.0032(13) C20 0.025(3) 0.018(2) 0.027(3) -0.0008(19) -0.004(2) 0.0069(18) O21 0.0244(17) 0.0279(16) 0.0230(16) 0.0007(13) 0.0025(13) -0.0025(13) C21 0.020(2) 0.024(2) 0.021(2) 0.0010(17) 0.0010(17) 0.0052(16) O22 0.0233(19) 0.043(2) 0.0277(18) 0.0010(16) 0.0033(15) -0.0028(15) C22 0.021(2) 0.031(2) 0.024(2) 0.0036(18) 0.0016(18) 0.0040(18) C23 0.022(3) 0.046(3) 0.032(3) -0.006(2) 0.006(2) 0.000(2) C24 0.023(2) 0.051(3) 0.027(2) -0.012(2) -0.002(2) -0.003(2) C25 0.030(3) 0.034(2) 0.020(2) -0.001(2) 0.001(2) -0.0020(19) C26 0.022(2) 0.029(2) 0.023(2) -0.0019(18) 0.0041(18) 0.0037(18) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 C1 O1 O2 . . 112.3(3) ? O1 C1 C2 . . 109.1(3) ? O1 C1 C11 . . 107.0(4) ? O1 C1 C12 . . 105.1(4) ? C2 C1 C11 . . 112.0(4) ? C12 C1 C2 . . 110.5(4) ? C12 C1 C11 . . 112.8(4) ? C3 O2 O1 . . 108.2(3) ? O3 C2 C1 . . 113.9(4) ? O3 C2 N11 . . 108.5(3) ? N11 C2 C1 . . 111.4(4) ? C2 O3 C3 . . 113.0(3) ? O2 C3 O3 . . 108.1(3) ? O2 C3 C4 . . 111.7(4) ? O2 C3 C13 . . 104.8(4) ? O3 C3 C4 . . 110.8(3) ? O3 C3 C13 . . 106.5(4) ? C13 C3 C4 . . 114.5(4) ? C3 C4 C5 . . 114.3(4) ? C11 C5 C4 . . 116.8(4) ? C7 C6 C11 . . 110.9(4) ? C7 C6 C14 . . 112.1(5) ? C14 C6 C11 . . 111.9(5) ? C6 C7 C8 . . 113.0(4) ? C7 C8 C12 . . 110.4(4) ? C10 C9 C12 . . 113.5(4) ? C10 C9 C15 . . 112.1(3) ? C15 C9 C12 . . 114.2(4) ? O10 C10 C9 . . 119.9(4) ? O10 C10 N11 . . 121.0(4) ? N11 C10 C9 . . 118.9(4) ? C10 N11 C2 . . 127.4(4) ? C1 C11 C6 . . 112.1(4) ? C5 C11 C1 . . 113.4(4) ? C5 C11 C6 . . 110.4(4) ? C1 C12 C8 . . 109.9(4) ? C1 C12 C9 . . 110.7(4) ? C9 C12 C8 . . 115.9(4) ? O20 C20 C21 . . 115.0(4) ? O21 C20 O20 . . 123.6(5) ? O21 C20 C21 . . 121.4(5) ? C22 C21 C20 . . 119.2(4) ? C26 C21 C20 . . 121.2(4) ? C26 C21 C22 . . 119.5(4) ? O22 C22 C21 . . 123.0(4) ? O22 C22 C23 . . 117.9(4) ? C23 C22 C21 . . 119.1(4) ? C24 C23 C22 . . 120.5(4) ? C23 C24 C25 . . 120.2(4) ? C24 C25 Br5 . . 119.4(4) ? C26 C25 Br5 . . 120.1(4) ? C26 C25 C24 . . 120.5(4) ? C25 C26 C21 . . 120.3(4) ? 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 O1 C1 . 1.458(5) ? O1 O2 . 1.469(4) ? C1 C2 . 1.526(6) ? C1 C11 . 1.538(6) ? C1 C12 . 1.522(6) ? O2 C3 . 1.413(5) ? C2 O3 . 1.413(5) ? C2 N11 . 1.454(6) ? O3 C3 . 1.435(5) ? C3 C4 . 1.530(6) ? C3 C13 . 1.515(6) ? C4 C5 . 1.536(6) ? C5 C11 . 1.531(7) ? C6 C7 . 1.521(8) ? C6 C11 . 1.543(6) ? C6 C14 . 1.526(7) ? C7 C8 . 1.522(7) ? C8 C12 . 1.539(6) ? C9 C10 . 1.509(5) ? C9 C12 . 1.537(6) ? C9 C15 . 1.530(6) ? O10 C10 . 1.254(5) ? C10 N11 . 1.329(6) ? Br5 C25 . 1.892(5) ? O20 C20 . 1.313(6) ? C20 O21 . 1.233(6) ? C20 C21 . 1.482(6) ? C21 C22 . 1.405(6) ? C21 C26 . 1.398(6) ? O22 C22 . 1.351(5) ? C22 C23 . 1.404(7) ? C23 C24 . 1.367(7) ? C24 C25 . 1.395(6) ? C25 C26 . 1.369(6) ? 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 N11 H11 O21 . 0.88(6) 2.12(6) 2.917(5) 150(5) O22 H22 O21 . 0.81(5) 1.85(5) 2.575(4) 147(5) O20 H20 O10 . 0.88(7) 1.66(7) 2.541(4) 179(8) 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 O1 C1 C2 O3 . . . . -54.5(5) ? O1 C1 C2 N11 . . . . 68.6(5) ? O1 C1 C11 C5 . . . . 66.4(5) ? O1 C1 C11 C6 . . . . -167.9(4) ? O1 C1 C12 C8 . . . . 171.9(4) ? O1 C1 C12 C9 . . . . -58.9(5) ? O1 O2 C3 O3 . . . . -74.2(4) ? O1 O2 C3 C4 . . . . 48.0(4) ? O1 O2 C3 C13 . . . . 172.5(3) ? C1 O1 O2 C3 . . . . 46.3(4) ? C1 C2 O3 C3 . . . . 29.2(5) ? C1 C2 N11 C10 . . . . 23.4(6) ? O2 O1 C1 C2 . . . . 14.6(5) ? O2 O1 C1 C11 . . . . -106.7(4) ? O2 O1 C1 C12 . . . . 133.1(3) ? O2 C3 C4 C5 . . . . -95.3(4) ? C2 C1 C11 C5 . . . . -53.2(5) ? C2 C1 C11 C6 . . . . 72.6(5) ? C2 C1 C12 C8 . . . . -70.5(5) ? C2 C1 C12 C9 . . . . 58.7(5) ? C2 O3 C3 O2 . . . . 33.5(5) ? C2 O3 C3 C4 . . . . -89.2(4) ? C2 O3 C3 C13 . . . . 145.7(4) ? O3 C2 N11 C10 . . . . 149.5(4) ? O3 C3 C4 C5 . . . . 25.3(6) ? C3 C4 C5 C11 . . . . 55.3(6) ? C4 C5 C11 C1 . . . . -33.8(6) ? C4 C5 C11 C6 . . . . -160.5(4) ? C6 C7 C8 C12 . . . . 57.6(5) ? C7 C6 C11 C1 . . . . 50.4(5) ? C7 C6 C11 C5 . . . . 177.7(4) ? C7 C8 C12 C1 . . . . -57.2(5) ? C7 C8 C12 C9 . . . . 176.4(4) ? C9 C10 N11 C2 . . . . -10.2(6) ? O10 C10 N11 C2 . . . . 174.4(4) ? C10 C9 C12 C1 . . . . -45.1(5) ? C10 C9 C12 C8 . . . . 80.8(5) ? N11 C2 O3 C3 . . . . -95.5(4) ? C11 C1 C2 O3 . . . . 63.8(5) ? C11 C1 C2 N11 . . . . -173.1(3) ? C11 C1 C12 C8 . . . . 55.7(5) ? C11 C1 C12 C9 . . . . -175.1(3) ? C11 C6 C7 C8 . . . . -53.7(6) ? C12 C1 C2 O3 . . . . -169.6(3) ? C12 C1 C2 N11 . . . . -46.5(5) ? C12 C1 C11 C5 . . . . -178.5(4) ? C12 C1 C11 C6 . . . . -52.8(5) ? C12 C9 C10 O10 . . . . -163.9(4) ? C12 C9 C10 N11 . . . . 20.7(6) ? C13 C3 C4 C5 . . . . 145.8(4) ? C14 C6 C7 C8 . . . . -179.5(4) ? C14 C6 C11 C1 . . . . 176.3(4) ? C14 C6 C11 C5 . . . . -56.3(6) ? C15 C9 C10 O10 . . . . -32.6(6) ? C15 C9 C10 N11 . . . . 151.9(4) ? C15 C9 C12 C1 . . . . -175.3(4) ? C15 C9 C12 C8 . . . . -49.4(6) ? Br5 C25 C26 C21 . . . . -178.7(3) ? O20 C20 C21 C22 . . . . 179.7(4) ? O20 C20 C21 C26 . . . . 3.0(6) ? C20 C21 C22 O22 . . . . 2.4(6) ? C20 C21 C22 C23 . . . . -176.6(4) ? C20 C21 C26 C25 . . . . 175.2(4) ? O21 C20 C21 C22 . . . . -0.2(6) ? O21 C20 C21 C26 . . . . -176.8(4) ? C21 C22 C23 C24 . . . . 1.6(7) ? O22 C22 C23 C24 . . . . -177.4(4) ? C22 C21 C26 C25 . . . . -1.5(6) ? C22 C23 C24 C25 . . . . -2.0(8) ? C23 C24 C25 Br5 . . . . -179.5(4) ? C23 C24 C25 C26 . . . . 0.7(8) ? C24 C25 C26 C21 . . . . 1.0(7) ? C26 C21 C22 O22 . . . . 179.1(4) ? C26 C21 C22 C23 . . . . 0.2(6) ?