#------------------------------------------------------------------------------ #$Date: 2018-01-13 08:36:00 +0200 (Sat, 13 Jan 2018) $ #$Revision: 205189 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/86/1548681.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_1548681 loop_ _publ_author_name 'El-Hiti, Gamal A.' 'Smith, Keith' 'Hegazy, Amany S.' 'Alshammari, Mohammed B.' 'Kariuki, Benson M.' _publ_section_title ; Methyl N-(2-bromo-4-chlorophenyl)carbamate ; _journal_coeditor_code SJ4153 _journal_issue 1 _journal_name_full IUCrData _journal_page_first x180054 _journal_paper_doi 10.1107/S2414314618000548 _journal_volume 3 _journal_year 2018 _chemical_formula_iupac 'C8 H7 Br Cl N O2' _chemical_formula_moiety 'C8 H7 Br Cl N O2' _chemical_formula_sum 'C8 H7 Br Cl N O2' _chemical_formula_weight 264.51 _chemical_name_systematic ; Methyl N-(2-bromo-4-chlorophenyl)carbamate ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2013 _cell_angle_alpha 111.639(5) _cell_angle_beta 101.035(5) _cell_angle_gamma 93.712(5) _cell_formula_units_Z 2 _cell_length_a 4.6637(3) _cell_length_b 9.4598(6) _cell_length_c 11.9898(7) _cell_measurement_reflns_used 2127 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 74.0500 _cell_measurement_theta_min 5.0680 _cell_volume 477.25(6) _computing_cell_refinement ; CrysAlis PRO (Agilent, 2014) ; _computing_data_collection ; CrysAlis PRO (Agilent, 2014) ; _computing_data_reduction ; CrysAlis PRO (Agilent, 2014) ; _computing_molecular_graphics ; ORTEP-3 for Windows (Farrugia, 2012) ; _computing_publication_material ; WinGX (Farrugia, 2012) and CHEMDRAW Ultra (Cambridge Soft, 2001) ; _computing_structure_refinement ; SHELXL2013 (Sheldrick, 2015) ; _computing_structure_solution ; SHELXS2013 (Sheldrick, 2008) ; _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.954 _diffrn_measurement_device_type 'Agilent SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 2938 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.969 _diffrn_reflns_theta_min 4.078 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 8.191 _exptl_absorpt_correction_T_max 0.891 _exptl_absorpt_correction_T_min 0.776 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; (CrysAlis PRO; Agilent, 2014) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.841 _exptl_crystal_description block _exptl_crystal_F_000 260 _exptl_crystal_size_max 0.305 _exptl_crystal_size_mid 0.203 _exptl_crystal_size_min 0.150 _refine_diff_density_max 0.303 _refine_diff_density_min -0.607 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 119 _refine_ls_number_reflns 1847 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.076 _refine_ls_R_factor_all 0.0248 _refine_ls_R_factor_gt 0.0239 _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^)+(0.0400P)^2^+0.1570P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0627 _refine_ls_wR_factor_ref 0.0633 _reflns_number_gt 1777 _reflns_number_total 1847 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file sj4153sup1.cif _cod_data_source_block I _cod_original_cell_volume 477.25(5) _cod_database_code 1548681 _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 0.189 _shelx_estimated_absorpt_t_max 0.373 _shelx_hkl_file ; -5 -4 5 26927.1 1110.08 13 -5 -4 6 7373.14 607.244 13 -5 -4 7 72032.4 1829.18 13 -5 -4 8 40978.6 1303.32 13 -5 -4 9 3801.12 367.660 13 -5 -3 -1 16635.9 783.522 7 -5 -3 0 711.727 228.047 7 -5 -3 1 56415.9 1687.01 7 -5 -3 2 27538.2 1198.16 7 -5 -3 3 3974.12 458.184 7 -5 -3 4 46002.5 1499.72 13 -5 -3 5 44194.0 1563.10 13 -5 -3 6 11201.4 804.057 13 -5 -3 7 67860.8 1927.78 13 -5 -3 8 16702.6 910.025 13 -5 -3 9 52.5812 142.066 13 -5 -2 -2 65917.4 1627.77 7 -5 -2 -1 22596.0 1091.48 7 -5 -2 0 14451.6 944.049 7 -5 -2 1 71553.5 2130.24 7 -5 -2 2 50278.8 1786.53 7 -5 -2 3 610.266 245.555 7 -5 -2 4 132396. 2723.26 13 -5 -2 4 147086. 2837.48 7 -5 -2 5 15285.7 971.417 13 -5 -2 6 590.526 272.721 13 -5 -2 7 54731.4 1787.50 13 -5 -2 8 13104.0 829.423 13 -5 -2 9 2149.65 334.907 13 -5 -1 -3 548.562 182.082 7 -5 -1 -2 32249.2 1299.98 7 -5 -1 -1 8745.25 761.706 7 -5 -1 0 1064.03 337.855 7 -5 -1 1 17491.2 1129.19 7 -5 -1 2 8563.04 802.935 7 -5 -1 3 10297.2 859.251 7 -5 -1 4 47978.2 1749.43 7 -5 -1 4 41879.9 1577.98 13 -5 -1 5 5503.66 614.557 13 -5 -1 6 33246.1 1439.81 13 -5 -1 7 56968.9 1816.57 13 -5 -1 8 47850.4 1565.17 13 -5 -1 9 4231.48 438.170 13 -5 0 -3 3358.45 423.478 7 -5 0 -2 48750.8 1698.78 7 -5 0 -1 7779.78 749.224 7 -5 0 0 62483.9 2135.74 7 -5 0 1 23811.0 1348.80 7 -5 0 2 45302.6 1848.51 7 -5 0 3-221.828 273.093 7 -5 0 4 24083.2 1189.31 13 -5 0 4 23455.7 1274.98 7 -5 0 5 61790.9 1894.71 7 -5 0 5 57545.2 1861.42 13 -5 0 6 12922.6 894.190 13 -5 0 7 6266.57 626.395 13 -5 0 8 50200.0 1569.11 13 -5 0 9 258.466 163.188 13 -5 1 -4 14702.5 734.228 7 -5 1 -3 13801.0 855.543 7 -5 1 -2 40222.9 1594.49 7 -5 1 -1 51825.3 1913.66 7 -5 1 0 35327.0 1638.48 7 -5 1 1 103741. 2798.31 7 -5 1 2 70518.5 2309.63 7 -5 1 3 17477.6 1160.89 7 -5 1 4 75327.0 2267.31 7 -5 1 4 72840.5 2029.70 13 -5 1 5 60429.0 1885.99 7 -5 1 5 59217.7 1847.97 13 -5 1 6 9380.86 742.404 13 -5 1 7 26324.5 1173.59 13 -5 1 8 256.857 174.923 13 -5 1 9 12107.4 644.234 13 -5 2 -4 21343.3 911.185 7 -5 2 -3 119.350 192.224 7 -5 2 -2 33855.9 1473.28 7 -5 2 -1 68534.9 2197.17 7 -5 2 0 231.533 278.735 7 -5 2 1 44198.2 1842.34 7 -5 2 2 405.185 307.926 7 -5 2 3 17705.3 1158.33 7 -5 2 4 45169.9 1713.25 7 -5 2 4 40579.9 1470.16 13 -5 2 5 1887.38 364.217 13 -5 2 6 21386.7 1055.74 13 -5 2 7 92360.3 2050.06 13 -5 2 8 1155.74 227.889 13 -5 3 -4 19996.6 846.895 7 -5 3 -3 4202.49 501.248 7 -5 3 -2 93700.0 2394.78 7 -5 3 -1 12898.4 951.859 7 -5 3 0 454.126 265.130 7 -5 3 1 74557.3 2314.14 7 -5 3 2 11907.3 943.484 7 -5 3 3 633.801 289.570 7 -5 3 4 37281.2 1330.68 13 -5 3 5 4212.28 464.584 13 -5 3 6 524.348 202.575 13 -5 3 7 57939.2 1425.30 13 -5 4 -3 715.348 241.244 8 -5 4 -3 507.597 211.191 7 -5 4 -2 18927.7 1022.94 7 -5 4 -1 4093.04 543.182 7 -5 4 0 6083.52 644.409 7 -5 4 1 119937. 2738.92 7 -5 4 3 10007.7 732.576 8 -5 4 4 60573.1 1531.24 8 -5 4 5 19620.2 817.368 13 -5 5 -3 229.233 156.607 8 -5 5 -2 6202.00 573.083 8 -5 5 -1 14170.4 892.338 8 -5 5 0 5051.91 555.618 8 -5 5 1 7358.07 641.929 8 -5 5 2 7189.80 589.941 8 -5 5 3 11401.3 637.334 8 -5 6 -2 44604.0 1238.88 8 -5 6 -1 20916.9 897.078 8 -5 6 0 2712.18 355.002 8 -5 6 1 9101.37 567.800 8 -5 6 2 10064.0 522.720 8 -4 -6 -1 61831.9 1449.61 4 -4 -6 0 1485.79 299.847 4 -4 -6 1 42990.6 1527.43 4 -4 -6 2 57378.7 1816.15 4 -4 -6 2 59157.2 1614.11 7 -4 -6 3 17428.7 997.645 4 -4 -6 10 75684.1 1839.01 13 -4 -5 -2 36445.3 1288.35 4 -4 -5 -1 13557.9 913.452 4 -4 -5 0 10864.7 891.700 4 -4 -5 1 128104. 3113.75 4 -4 -5 2 30703.9 1536.63 4 -4 -5 3 3061.30 459.079 7 -4 -5 3 2794.03 493.386 4 -4 -5 4 106189. 2660.50 4 -4 -5 10 209432. 3378.72 13 -4 -5 11 7829.84 564.068 13 -4 -4 -4 1533.56 243.987 7 -4 -4 -3 5097.03 523.269 4 -4 -4 -2 82061.9 2351.29 4 -4 -4 -1 3251.58 566.972 4 -4 -4 0 1359.02 422.999 4 -4 -4 1 142676. 3557.31 4 -4 -4 2 40829.3 1892.75 4 -4 -4 3 12824.6 1055.78 4 -4 -4 3 12584.4 946.309 7 -4 -4 4 279232. 4581.51 4 -4 -4 10 130773. 2837.09 13 -4 -4 11 24371.6 1051.80 13 -4 -3 -5 47654.3 1230.93 7 -4 -3 -3 184.191 208.923 4 -4 -3 -2 70456.8 2408.81 4 -4 -3 -1 37219.5 1844.08 4 -4 -3 0 8956.57 926.291 4 -4 -3 1 20993.5 1424.52 4 -4 -3 2 17892.7 1283.20 4 -4 -3 3 32543.6 1579.74 7 -4 -3 3 29298.6 1580.67 4 -4 -3 9 65879.4 2240.45 13 -4 -3 10 41069.7 1629.27 13 -4 -3 11 40327.6 1391.48 13 -4 -2 -5 40271.8 1391.51 7 -4 -2 -3 32544.8 1616.46 4 -4 -2 -2 111731. 3155.21 4 -4 -2 -1 15329.4 1239.12 4 -4 -2 0 156634. 3839.23 4 -4 -2 1 37166.2 1859.41 4 -4 -2 2 68353.1 2363.25 7 -4 -2 2 64633.1 2376.68 4 -4 -2 3 18152.7 1211.63 7 -4 -2 4 52516.9 1951.47 7 -4 -2 8 153649. 3567.19 13 -4 -2 9-83.2003 266.071 13 -4 -2 10 22108.6 1198.39 13 -4 -2 11 26846.7 1136.03 13 -4 -1 -6 28643.7 1051.80 7 -4 -1 -6 27650.2 1006.74 14 -4 -1 -5 9679.27 770.491 7 -4 -1 -4 16697.1 1125.17 7 -4 -1 -3 40675.4 1858.05 4 -4 -1 -2 35971.3 1808.25 4 -4 -1 -1 23758.5 1497.14 4 -4 -1 0 155666. 3779.30 4 -4 -1 1 172276. 3783.85 7 -4 -1 1 169173. 3858.54 4 -4 -1 2 71628.5 2413.61 7 -4 -1 3 68625.8 2312.54 7 -4 -1 4 165565. 3515.66 7 -4 -1 7 124219. 3245.51 13 -4 -1 8 796.037 383.641 13 -4 -1 9 23957.3 1329.66 13 -4 -1 10 48794.1 1726.15 13 -4 -1 11 7406.88 601.929 13 -4 0 -7 35121.9 1085.48 14 -4 0 -6 14380.0 853.185 14 -4 0 -6 14190.5 818.083 7 -4 0 -5 77849.4 2139.76 14 -4 0 -5 79466.2 2265.85 7 -4 0 -4 41383.8 1796.64 7 -4 0 -3 144.953 291.534 7 -4 0 -2 84573.2 2716.02 7 -4 0 -1 130854. 3351.46 7 -4 0 0-239.351 316.249 7 -4 0 1 128913. 3260.96 7 -4 0 2-121.949 236.863 7 -4 0 3 21787.0 1319.76 7 -4 0 4 104820. 2863.99 13 -4 0 4 107815. 2873.47 7 -4 0 5-1.07615 211.723 13 -4 0 5 254.253 232.952 7 -4 0 6 47809.0 1998.58 13 -4 0 7 156723. 3573.96 13 -4 0 8 62110.6 2201.66 13 -4 0 9 64722.1 2115.28 13 -4 0 10 99619.6 2403.03 13 -4 0 11 7.22337 123.987 13 -4 1 -7 16886.4 873.944 14 -4 1 -6 4840.66 503.612 7 -4 1 -6 3965.02 510.034 14 -4 1 -5 137195. 2980.44 14 -4 1 -5 140988. 3074.96 7 -4 1 -4 13868.4 1059.82 7 -4 1 -3 37038.1 1763.80 7 -4 1 -2 314481. 5139.94 7 -4 1 -1 13440.0 1090.31 7 -4 1 0 10834.1 985.060 7 -4 1 1 216998. 4203.99 7 -4 1 2 3856.96 610.090 7 -4 1 2 2703.16 463.185 13 -4 1 3 22571.7 1362.27 7 -4 1 3 24222.4 1334.32 13 -4 1 4 168485. 3590.42 13 -4 1 4 156902. 3545.65 7 -4 1 5 7280.59 787.773 7 -4 1 5 7647.02 813.362 13 -4 1 6 189.654 278.669 13 -4 1 7 148527. 3388.88 13 -4 1 8 49731.8 1909.24 13 -4 1 9 4639.82 576.162 13 -4 1 10 38211.1 1422.27 13 -4 1 11 224.918 132.928 13 -4 2 -8 31061.4 1018.74 14 -4 2 -7 2043.08 352.830 14 -4 2 -6 30.1818 184.883 14 -4 2 -5 55874.9 1929.52 7 -4 2 -5 53339.3 1887.43 14 -4 2 -4 653.705 320.812 7 -4 2 -3 8333.98 849.422 7 -4 2 -2 47639.8 1999.82 7 -4 2 -1 401.516 302.100 7 -4 2 0 36457.8 1746.78 7 -4 2 1 216880. 4237.30 7 -4 2 2 44838.3 1738.70 13 -4 2 2 44125.1 1917.42 7 -4 2 3 77366.5 2539.23 7 -4 2 3 76268.8 2339.58 13 -4 2 4 136574. 3384.39 7 -4 2 4 144128. 3269.95 13 -4 2 5 28569.6 1519.93 7 -4 2 5 28139.3 1470.80 13 -4 2 6 63572.1 2200.00 13 -4 2 7 123216. 3035.18 13 -4 2 8 50719.5 1872.19 13 -4 2 9 37764.3 1490.89 13 -4 2 10 16461.2 851.370 13 -4 3 -8 31026.3 1075.86 14 -4 3 -7 19022.2 994.047 14 -4 3 -6 14695.7 968.551 14 -4 3 -5 37375.2 1549.14 7 -4 3 -5 37444.2 1565.27 14 -4 3 -4 35155.7 1618.16 7 -4 3 -4 37104.4 1544.07 14 -4 3 -3 436.283 263.945 7 -4 3 -2 15275.4 1140.82 7 -4 3 -1 55668.4 2157.58 7 -4 3 0 25011.2 1450.26 7 -4 3 1 31848.4 1661.00 7 -4 3 2 57044.6 1993.25 13 -4 3 2 58993.2 2280.30 7 -4 3 3 34382.0 1595.84 13 -4 3 3 35016.0 1754.56 7 -4 3 4 40756.7 1763.72 13 -4 3 4 39750.6 1834.38 7 -4 3 5 13957.5 1050.69 13 -4 3 6 89491.5 2577.67 13 -4 3 7 7192.51 735.535 13 -4 3 8 384.487 262.272 13 -4 3 9 68315.1 1791.33 13 -4 3 10 33608.7 966.828 13 -4 4 -8 3483.92 385.763 14 -4 4 -7 7426.26 631.022 14 -4 4 -6 37079.2 1472.52 14 -4 4 -5 59144.9 1884.67 7 -4 4 -5 60227.4 1926.94 14 -4 4 -4 18849.0 1164.79 7 -4 4 -4 19100.0 1099.94 14 -4 4 -3 154671. 3440.40 7 -4 4 -2 107077. 2941.29 7 -4 4 -1 25896.4 1500.29 7 -4 4 0 57512.0 2240.66 7 -4 4 1 50882.7 2100.13 7 -4 4 2 19912.9 1195.61 13 -4 4 2 20983.9 1372.33 7 -4 4 3 40361.6 1729.01 13 -4 4 3 39980.4 1854.44 7 -4 4 4 29934.6 1490.18 13 -4 4 4 29164.3 1432.42 8 -4 4 5 25303.1 1366.06 13 -4 4 6 491.106 271.116 13 -4 4 7 16534.8 1005.81 13 -4 4 8 10224.9 711.031 13 -4 4 9 3728.04 350.021 13 -4 5 -8 12222.8 653.045 14 -4 5 -8 11728.0 639.800 9 -4 5 -7 4981.19 504.140 14 -4 5 -6 17352.6 969.850 14 -4 5 -5 37008.8 1525.89 8 -4 5 -5 38484.6 1479.28 14 -4 5 -4 26.8383 196.734 7 -4 5 -4-3.10131 156.337 14 -4 5 -3 56397.2 2026.88 7 -4 5 -2 43770.5 1850.80 7 -4 5 -1 1463.04 440.692 7 -4 5 0 12542.3 1045.54 7 -4 5 1 58258.7 2214.80 7 -4 5 2 316.053 283.795 8 -4 5 2 295.487 236.281 13 -4 5 3 28576.0 1424.08 8 -4 5 3 28630.0 1411.72 13 -4 5 4 66677.3 2120.93 13 -4 5 4 64123.8 1895.04 8 -4 5 5 902.519 286.389 13 -4 5 6 23592.2 1147.25 13 -4 5 7 72652.8 1770.95 13 -4 5 8 569.137 171.443 13 -4 6 -8 82156.8 1575.23 9 -4 6 -7 2477.28 331.020 14 -4 6 -6 4883.13 493.956 14 -4 6 -5 41614.0 1443.55 14 -4 6 -5 40932.2 1474.10 8 -4 6 -4 17796.6 1113.79 8 -4 6 -3 406.926 289.795 8 -4 6 -2 45665.9 1913.08 8 -4 6 -1 4173.82 625.030 8 -4 6 0 6982.03 785.459 8 -4 6 1 35626.5 1612.21 8 -4 6 2 957.033 263.147 13 -4 6 2 612.690 278.377 8 -4 6 3 12556.8 817.853 8 -4 6 3 11887.1 827.808 13 -4 6 4 62698.6 1809.76 13 -4 6 5 12772.4 775.096 13 -4 6 6 32829.1 1085.09 13 -4 7 -7-7.35649 137.879 9 -4 7 -6 9447.55 660.261 9 -4 7 -5 55463.7 1471.42 8 -4 7 -4 3513.65 452.523 8 -4 7 -3 37943.4 1507.86 8 -4 7 -2 114152. 2701.91 8 -4 7 -1 656.002 307.212 8 -4 7 0 78075.1 2177.78 8 -4 7 1 69786.8 1919.24 8 -4 7 2 1766.96 318.756 8 -4 7 3 13910.1 673.987 8 -4 7 3 14744.5 744.964 13 -4 7 4 27399.2 945.034 13 -4 8 -6 23836.4 793.966 9 -4 8 -5 14335.1 650.429 9 -4 8 -4 178.243 130.073 9 -4 8 -4 187.913 153.611 8 -4 8 -3 21066.7 935.230 8 -4 8 -2 46073.1 1411.20 8 -4 8 -1 25408.1 1042.08 8 -4 8 0 34055.5 1151.92 8 -4 8 1 18376.3 775.350 8 -3 -8 0 907.165 217.399 4 -3 -8 1 51349.3 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4352.44 18 2 3 -4 439094. 4490.66 17 2 3 -3 409519. 4233.57 18 2 3 -2 112922. 2238.53 18 2 3 -1 470369. 4621.70 18 2 3 0 69899.0 1830.74 18 2 3 1 7223.19 619.748 18 2 3 2 505523. 5294.09 18 2 3 3 52197.7 2135.97 15 2 3 4 817.439 433.094 15 2 4 -14 16260.7 890.775 12 2 4 -13 87892.5 2411.31 12 2 4 -12 17079.7 1198.69 12 2 4 -12 17031.2 1048.81 5 2 4 -11 38422.9 1715.19 5 2 4 -11 36839.1 1807.47 12 2 4 -11 37932.2 1764.57 11 2 4 -10 100977. 3002.47 12 2 4 -10 103914. 2881.24 11 2 4 -9 100425. 2718.56 11 2 4 -9 95002.8 2577.01 17 2 4 -9 97187.7 2518.81 10 2 4 -8 293887. 4909.82 6 2 4 -8 290966. 4347.89 11 2 4 -8 290210. 4276.26 10 2 4 -7 310395. 4884.61 6 2 4 -7 305793. 4292.97 10 2 4 -6 58552.8 1894.35 17 2 4 -5 238.676 187.225 17 2 4 -4 406552. 4600.97 17 2 4 -3 7741.96 632.975 17 2 4 -2 6155.16 609.150 18 2 4 -1 638307. 6082.34 18 2 4 2 194946. 4071.39 15 2 4 3 27922.7 1603.35 15 2 5 -14 32045.9 1133.17 12 2 5 -13 150259. 2925.33 12 2 5 -13 155784. 2803.78 5 2 5 -12 28109.1 1399.41 12 2 5 -12 30748.4 1515.39 11 2 5 -12 29130.7 1436.79 5 2 5 -11 2713.67 499.316 5 2 5 -11 2506.27 460.906 12 2 5 -11 2785.50 506.110 11 2 5 -10 111794. 2930.44 12 2 5 -10 118868. 3039.97 11 2 5 -9 19315.6 1205.04 12 2 5 -9 20049.8 1223.59 11 2 5 -8 1091.28 339.095 17 2 5 -8 1060.74 303.464 11 2 5 -8 914.926 329.999 6 2 5 -8 554.364 206.261 10 2 5 -7 271965. 4105.72 11 2 5 -7 273176. 4463.54 17 2 5 -7 271732. 4797.89 6 2 5 -7 267428. 4251.99 10 2 5 -6 144138. 3165.73 17 2 5 -6 147415. 3402.65 6 2 5 -6 150544. 3155.14 10 2 5 -5 4687.13 564.299 17 2 5 -5 5439.25 609.819 10 2 5 -4 119222. 2650.12 17 2 5 -4 116971. 2791.77 10 2 5 -3 126750. 2665.87 17 2 5 -2 502.204 234.563 17 2 5 -1 114843. 2482.15 17 2 5 0 343534. 4855.60 15 2 5 1 630.363 274.089 15 2 6 -13 28153.9 1071.09 12 2 6 -13 30296.7 1268.54 5 2 6 -12 67833.7 1877.09 12 2 6 -12 75742.7 2250.71 11 2 6 -12 71794.2 2249.77 5 2 6 -11 34768.1 1719.91 5 2 6 -11 36920.7 1653.15 11 2 6 -10 93555.6 2677.84 11 2 6 -9 31143.6 1538.73 11 2 6 -9 30995.0 1466.33 10 2 6 -8 127213. 2983.18 11 2 6 -8 125697. 3411.77 6 2 6 -8 127872. 3047.32 10 2 6 -7 59857.0 2010.63 11 2 6 -7 62133.0 2203.26 17 2 6 -7 61253.4 2336.26 6 2 6 -7 59964.1 2102.44 10 2 6 -6 295591. 4726.01 17 2 6 -6 285926. 4624.21 10 2 6 -5 46846.1 1833.84 17 2 6 -5 45881.7 1907.94 6 2 6 -5 45439.1 1858.85 10 2 6 -4 129409. 2940.00 17 2 6 -3 249640. 3920.77 17 2 6 -2 11186.9 834.028 17 2 7 -13 6589.39 570.201 5 2 7 -12 119946. 2621.57 11 2 7 -12 119257. 2756.31 5 2 7 -11 15833.5 1122.49 5 2 7 -11 16172.5 1040.72 11 2 7 -10 22674.9 1266.85 11 2 7 -9 202813. 3782.74 11 2 7 -9 211866. 3769.28 10 2 7 -8 2979.33 504.425 11 2 7 -8 4796.37 701.786 6 2 7 -8 3700.23 548.131 10 2 7 -7 17274.4 1244.77 6 2 7 -7 15256.7 1107.54 10 2 7 -6 128996. 3300.97 6 2 7 -6 127828. 3227.58 10 2 7 -5 38296.8 1742.80 6 2 7 -5 38959.4 1798.58 10 2 7 -4 109041. 2796.10 6 2 7 -4 107446. 3038.58 10 2 7 -3 58529.7 1976.73 6 2 8 -13 48960.7 1325.38 5 2 8 -12 51811.2 1489.69 11 2 8 -12 54082.4 1657.18 5 2 8 -11 14136.7 964.954 5 2 8 -11 12967.1 826.486 11 2 8 -10 144469. 2893.45 11 2 8 -9 99313.4 2414.32 10 2 8 -9 98044.6 2425.43 11 2 8 -8 14557.5 944.866 11 2 8 -8 14772.2 1005.84 10 2 8 -7 147370. 3331.25 6 2 8 -7 145004. 3244.74 10 2 8 -6 19183.6 1185.85 6 2 8 -6 20454.3 1283.82 10 2 8 -5 79.8872 154.585 6 2 8 -5-38.3487 214.428 10 2 8 -4 152235. 3004.08 6 2 8 -4 159067. 3603.37 10 2 8 -3 32579.3 1640.84 10 2 8 1 8430.22 658.535 10 2 8 2 58150.4 1388.87 10 2 9 -12 21032.2 827.859 5 2 9 -11 47.4710 161.924 5 2 9 -11 152.926 134.270 11 2 9 -10 148845. 2711.10 5 2 9 -10 152088. 2410.06 11 2 9 -9 521.475 181.718 10 2 9 -8 9140.52 704.158 10 2 9 -7 235450. 3723.72 10 2 9 -6 11803.0 886.321 10 2 9 -5 4007.10 534.102 10 2 9 -4 174155. 3384.44 10 2 9 -3 15048.8 988.391 10 2 9 -2 237.923 230.553 10 2 9 -1 156694. 2749.31 10 2 9 0 25974.9 986.735 10 2 10 -8 997.483 197.261 10 2 10 -7 78308.4 1710.32 10 2 10 -6 31944.5 1151.25 10 2 10 -5 8237.06 599.217 10 2 10 -4 82289.4 1841.70 10 2 10 -3 30874.3 1070.78 10 2 10 -2 27886.4 917.291 10 3 -5 -9 20432.2 752.004 3 3 -5 -8 1214.38 254.492 3 3 -5 -7 8067.97 642.495 3 3 -5 -2 965.381 370.910 18 3 -5 -1 134048. 3385.70 18 3 -5 0 293192. 5058.32 18 3 -5 1 38126.3 1855.01 18 3 -5 2 169091. 3881.87 18 3 -5 3 70030.0 2485.59 18 3 -4 -10 14361.5 685.712 3 3 -4 -9 22769.2 1032.67 3 3 -4 -2 1418.64 363.952 18 3 -4 -1 107428. 2861.45 18 3 -4 0 6568.46 733.134 18 3 -4 1 17253.4 1171.29 18 3 -4 2 182556. 3761.57 18 3 -4 3 9926.88 896.038 18 3 -4 4 1898.33 432.506 18 3 -3 -11 1485.06 248.167 3 3 -3 -10 70822.4 1854.55 3 3 -3 -3 51051.0 1770.28 18 3 -3 -2 25565.9 1285.09 18 3 -3 -1 94135.9 2492.84 18 3 -3 0 23781.7 1269.90 18 3 -3 1 780.625 287.328 18 3 -3 2 146861. 3218.96 18 3 -3 3 177317. 3587.83 18 3 -3 4 688.457 290.813 18 3 -3 5 116832. 2906.27 18 3 -2 -12 4410.78 361.326 3 3 -2 -11 2065.53 340.799 3 3 -2 -10 88245.2 2116.85 12 3 -2 -3 224962. 3534.85 18 3 -2 -2 9480.96 749.604 18 3 -2 -1 135581. 2854.97 18 3 -2 0 269236. 4055.59 18 3 -2 1 5682.66 630.319 18 3 -2 2 104653. 2600.30 18 3 -2 3 317301. 4566.08 18 3 -2 4 26565.4 1352.22 18 3 -2 5 57450.6 1977.15 18 3 -1 -12 65766.4 1426.58 12 3 -1 -12 72295.0 1684.58 3 3 -1 -11 503.142 224.178 12 3 -1 -10 36278.0 1623.95 12 3 -1 -4 94249.9 2153.46 18 3 -1 -3 92375.9 2188.56 18 3 -1 -2 261747. 3752.09 18 3 -1 -1 114345. 2510.61 18 3 -1 0 122450. 2639.56 18 3 -1 1 128950. 2762.84 18 3 -1 2 32081.7 1411.31 18 3 -1 3 9941.17 808.553 18 3 -1 4 38457.6 1589.81 18 3 0 -12 92129.8 2176.45 12 3 0 -11 7055.39 733.485 12 3 0 -6 221273. 3818.06 10 3 0 -5 20419.5 1115.09 10 3 0 -4 164430. 2844.33 18 3 0 -3 246323. 3549.26 18 3 0 -2 14017.5 872.113 18 3 0 -1 226314. 3507.11 18 3 0 0 72368.0 2021.06 18 3 0 1 302.186 216.269 18 3 0 2 118488. 2704.04 18 3 0 3 39101.6 1594.38 18 3 0 4 1828.66 362.748 18 3 1 -13 24398.5 1010.34 12 3 1 -13 22520.4 832.199 3 3 1 -12 19202.9 1120.49 12 3 1 -11 1664.73 469.527 12 3 1 -7 283293. 4486.39 10 3 1 -6 8515.22 760.582 10 3 1 -5 652.502 223.913 17 3 1 -5 1295.22 320.351 10 3 1 -4 385698. 4494.60 18 3 1 -3 179990. 3110.87 18 3 1 -2 18676.1 1027.30 18 3 1 -1 408368. 4816.26 18 3 1 0 55034.3 1803.24 18 3 1 1 3347.69 484.738 18 3 1 2 526998. 5833.20 18 3 1 3 71614.8 2179.81 18 3 2 -13 116514. 2425.41 12 3 2 -12 11752.3 922.878 12 3 2 -11 12008.3 1058.43 12 3 2 -8 220347. 4069.78 10 3 2 -7 212296. 3903.80 6 3 2 -7 214641. 3902.07 10 3 2 -6 46576.3 1667.42 17 3 2 -6 48366.4 1803.42 10 3 2 -5 1412.30 324.029 18 3 2 -5 1037.43 298.223 17 3 2 -5 1125.30 318.885 10 3 2 -4 219758. 3510.87 18 3 2 -4 230155. 3735.19 10 3 2 -3 8695.98 715.887 18 3 2 -2 5003.72 561.055 18 3 2 -1 377463. 4789.04 18 3 2 0 7462.80 707.865 18 3 2 1 142197. 3054.65 18 3 2 2 167390. 3401.25 18 3 3 -14 10318.6 573.151 12 3 3 -13 110467. 2416.63 12 3 3 -12 10274.0 871.397 12 3 3 -11 1541.13 426.488 12 3 3 -9 36247.9 1672.99 6 3 3 -9 35922.5 1667.71 10 3 3 -8 898.543 336.296 6 3 3 -8-130.951 179.071 10 3 3 -7 253476. 4553.61 6 3 3 -7 248762. 4291.20 10 3 3 -6 127531. 2958.54 17 3 3 -6 140464. 3227.16 10 3 3 -5 35012.2 1511.98 18 3 3 -5 35259.2 1542.75 17 3 3 -5 36286.9 1602.53 10 3 3 -4 167232. 3316.40 18 3 3 -4 165562. 3361.17 10 3 3 -3 120653. 2829.43 18 3 3 -3 122695. 2836.66 10 3 3 -2 24823.1 1303.37 18 3 3 -2 25467.1 1302.48 10 3 3 -1 155302. 3290.19 18 3 3 -1 156465. 3153.86 10 3 3 0 294506. 4606.32 18 3 3 1 3864.86 559.822 18 3 4 -13 15427.9 864.480 12 3 4 -12 65683.3 2044.78 12 3 4 -11 42747.7 1816.43 12 3 4 -10 52012.1 1948.93 10 3 4 -9 3619.56 560.311 10 3 4 -9 2815.85 522.965 6 3 4 -8 210998. 4350.07 6 3 4 -8 217318. 4122.56 10 3 4 -7 50534.3 2004.54 17 3 4 -7 53267.0 2191.91 6 3 4 -7 53799.9 2075.79 10 3 4 -6 148096. 3365.03 17 3 4 -6 154134. 3464.02 10 3 4 -5 113773. 2906.75 17 3 4 -5 114169. 2959.20 10 3 4 -4 111215. 2835.39 17 3 4 -4 107130. 2852.41 10 3 4 -3 123853. 3107.79 18 3 4 -3 124998. 3086.07 10 3 4 -2 47832.5 1942.13 18 3 4 -2 45257.5 1845.06 10 3 4 -1 29788.1 1552.71 18 3 4 -1 29794.1 1486.86 10 3 4 0 266435. 4321.69 10 3 5 -13 19049.8 826.091 12 3 5 -12 102502. 2272.37 12 3 5 -12 108431. 2292.79 5 3 5 -11 26332.6 1259.82 12 3 5 -10 30157.0 1419.42 12 3 5 -10 34835.1 1554.71 10 3 5 -9 164631. 3837.87 6 3 5 -9 162961. 3530.86 10 3 5 -8 8100.24 904.336 6 3 5 -8 7752.42 806.966 10 3 5 -7 26447.0 1600.74 6 3 5 -7 26533.3 1493.04 10 3 5 -6 131510. 3461.27 6 3 5 -6 125821. 3240.09 10 3 5 -5 20459.8 1319.13 10 3 5 -4 93739.0 2795.32 10 3 5 -3 45363.7 1945.87 10 3 5 -2 55903.0 2150.29 10 3 5 -1 42530.9 1851.41 10 3 5 0 7565.88 783.962 10 3 6 -12 15802.8 885.284 5 3 6 -10 196674. 3508.22 10 3 6 -9 76690.4 2566.24 6 3 6 -9 73997.5 2318.61 10 3 6 -8 22143.9 1441.85 6 3 6 -8 23406.4 1395.43 10 3 6 -7 201432. 4261.69 6 3 6 -7 197690. 4062.21 10 3 6 -6 10345.3 992.393 6 3 6 -6 10485.1 968.687 10 3 6 -5 7264.69 825.028 10 3 6 -4 260953. 4766.39 10 3 6 -3 26090.2 1517.31 10 3 6 -2 16549.3 1184.33 10 3 6 -1 182402. 3717.44 10 3 6 0 1067.18 313.957 10 3 7 -12 12608.7 725.646 5 3 7 -10 193885. 3201.49 10 3 7 -9 1462.19 358.714 10 3 7 -8 23105.2 1363.48 6 3 7 -8 23639.7 1335.54 10 3 7 -7 243437. 4417.79 6 3 7 -7 237415. 4274.54 10 3 7 -6 194.706 255.771 6 3 7 -6 158.320 207.288 10 3 7 -5 25353.3 1394.98 6 3 7 -5 25962.4 1460.59 10 3 7 -4 161212. 3336.04 6 3 7 -4 170037. 3684.83 10 3 7 -3 1020.63 317.580 6 3 7 -3 1371.90 385.283 10 3 7 -2 13995.4 885.471 6 3 7 -2 14806.3 1042.17 10 3 7 -1 204468. 3517.70 10 3 7 0 31083.7 1219.07 10 3 8 -11 6358.43 518.732 5 3 8 -10 56231.4 1447.32 10 3 8 -9 23247.3 1071.53 10 3 8 -8 1046.92 294.942 10 3 8 -7 106311. 2513.82 6 3 8 -7 109617. 2603.51 10 3 8 -6 41952.2 1558.59 6 3 8 -6 45514.4 1725.11 10 3 8 -5 11217.2 784.014 6 3 8 -5 12398.1 920.279 10 3 8 -4 67493.2 1774.54 6 3 8 -4 75106.6 2177.52 10 3 8 -3 25642.5 1224.12 10 3 8 -2 51739.9 1592.48 10 3 8 -1 52833.0 1404.15 10 3 9 -10 55930.2 1227.12 5 3 9 -9 54543.5 1232.09 10 3 9 -8 56561.5 1426.07 10 3 9 -7 53631.0 1505.07 10 3 9 -6 67690.3 1714.34 10 3 9 -5 40505.7 1310.64 10 3 9 -4 72050.2 1670.28 10 3 9 -3 81730.4 1615.68 10 4 -4 -8 10107.5 581.569 3 4 -3 -10 36062.4 950.728 3 4 -1 -11 305.700 128.748 12 4 -1 -10 39827.0 1435.11 12 4 -1 -2 3237.40 565.578 18 4 0 -11 117.825 155.487 12 4 0 -3 22585.1 1372.67 18 4 0 -3 23064.0 1260.52 10 4 1 -12 885.292 208.720 12 4 1 -11 8410.44 710.177 12 4 1 -6 59030.5 2169.49 10 4 1 -5 82467.0 2514.45 10 4 1 -4 163582. 3456.11 10 4 1 -3 71461.3 2221.22 10 4 2 -12 50880.3 1456.65 12 4 2 -11 28253.4 1321.24 12 4 2 -7 22826.4 1385.88 10 4 2 -6 52063.3 2052.29 10 4 2 -5 111168. 2944.31 10 4 2 -4 52997.1 1990.14 10 4 2 -3 17792.6 1143.57 10 4 3 -12 51681.7 1433.74 12 4 3 -11 38595.8 1482.59 12 4 3 -8 29553.3 1450.62 6 4 3 -8 32241.2 1614.10 10 4 3 -7 57267.7 2164.67 10 4 3 -7 56371.8 2116.72 6 4 3 -6 95642.8 2804.15 10 4 3 -5 7222.04 791.891 10 4 3 -4 73383.4 2386.87 10 4 3 -3 31849.8 1538.12 10 4 3 -2 19346.2 1176.91 10 4 4 -12 1080.91 193.873 12 4 4 -11 20899.8 975.151 12 4 4 -9 22944.8 1201.19 6 4 4 -9 23094.1 1285.17 10 4 4 -8 22861.3 1325.87 6 4 4 -8 24581.5 1385.84 10 4 4 -7 145234. 3452.76 6 4 4 -7 146563. 3415.53 10 4 4 -6-143.480 276.344 6 4 4 -6 132.191 243.696 10 4 4 -5 23944.5 1388.32 10 4 4 -4 269875. 4654.55 10 4 4 -3 11755.6 946.594 10 4 4 -2 42475.8 1706.88 10 4 5 -9 387.112 216.862 6 4 5 -9 707.887 280.010 10 4 5 -8 21079.3 1253.14 6 4 5 -8 22848.1 1280.53 10 4 5 -7 155277. 3485.77 6 4 5 -7 154229. 3394.24 10 4 5 -6 7511.66 778.984 10 4 5 -6 7143.31 812.307 6 4 5 -5 43010.3 1817.67 10 4 5 -4 94699.7 2668.17 10 4 5 -3 2768.01 465.228 10 4 5 -2 32340.8 1401.16 10 4 6 -9 15795.8 927.559 10 4 6 -8 18213.0 1067.24 6 4 6 -8 17828.1 1035.20 10 4 6 -7 122822. 2849.15 6 4 6 -7 116647. 2753.61 10 4 6 -6 39450.5 1653.92 6 4 6 -6 37888.2 1591.43 10 4 6 -5 19625.9 1171.78 6 4 6 -5 19484.4 1152.52 10 4 6 -4 51988.5 1828.40 6 4 6 -4 51104.1 1790.49 10 4 6 -3 17190.0 988.069 10 4 6 -2 60069.2 1621.62 10 4 6 0 1318.65 200.132 6 4 7 -9 23890.3 958.069 10 4 7 -8 85824.9 1971.46 6 4 7 -8 84647.5 1938.48 10 4 7 -7 50442.2 1564.39 6 4 7 -7 49228.2 1549.54 10 4 7 -6 47029.1 1518.12 6 4 7 -6 46715.0 1519.62 10 4 7 -5 65638.2 1744.03 6 4 7 -5 66629.9 1781.24 10 4 7 -4 86583.5 1890.97 6 4 7 -4 89533.6 1942.04 10 4 7 -3 48351.0 1274.67 6 4 7 -3 50468.7 1283.04 10 5 2 -5 16575.1 951.514 6 5 3 -6 10672.8 730.776 6 5 3 -5 46430.9 1601.49 6 5 4 -7 70713.8 1602.41 6 5 4 -6 8268.79 620.334 6 5 4 -5 35442.9 1321.02 6 5 4 -4 31961.3 1257.98 6 5 5 -6 21983.1 873.704 6 5 5 -5 51400.0 1356.43 6 5 5 -4 56764.3 1403.94 6 5 5 -3 12495.1 624.669 6 0 0 0 0.00 0.00 0 TITL ks1504c in P1 REM P1 (#1 in standard setting) CELL 1.54184 4.663711 9.459797 11.989766 111.6393 101.0354 93.7116 ZERR 2.00 0.000310 0.000555 0.000672 0.0054 0.0053 0.0051 LATT -1 SFAC C H N O UNIT 16.00 20.00 2.00 4.00 TREF HKLF 4 END ; _shelx_hkl_checksum 50638 _shelx_res_file ; TITL ks1504c in P-1 CELL 1.54184 4.6637 9.4598 11.9898 111.639 101.035 93.712 ZERR 2.00 0.0003 0.0006 0.0007 0.005 0.005 0.005 LATT 1 SFAC C H N O CL BR UNIT 16 14 2 4 2 2 MERG 2 eqiv $1 x+1, y, z htab n1 o1_$1 mpla c1 c2 c3 c4 c5 c6 br1 cl1 mpla n1 c7 o1 o2 c8 FMAP 2 PLAN 10 SIZE 0.150 0.203 0.305 ACTA BOND $H L.S. 4 TEMP -123.00 WGHT 0.040000 0.157000 FVAR 13.08054 C1 1 0.583243 0.250775 0.089765 11.00000 0.01695 0.01812 = 0.01959 0.00749 0.00631 0.00470 C2 1 0.777438 0.365792 0.192082 11.00000 0.01769 0.01812 = 0.02229 0.00910 0.00581 0.00186 C3 1 0.777653 0.380636 0.311313 11.00000 0.02410 0.02148 = 0.02000 0.00703 0.00333 -0.00030 AFIX 43 H3 2 0.911500 0.458475 0.379609 11.00000 -1.20000 AFIX 0 C4 1 0.580302 0.280556 0.329503 11.00000 0.03097 0.02687 = 0.01938 0.01214 0.00970 0.00537 C5 1 0.386607 0.165374 0.231492 11.00000 0.02394 0.02191 = 0.02638 0.01152 0.00993 0.00128 AFIX 43 H5 2 0.252511 0.097264 0.245518 11.00000 -1.20000 AFIX 0 C6 1 0.390337 0.150422 0.112504 11.00000 0.02021 0.01970 = 0.02223 0.00721 0.00581 0.00016 AFIX 43 H6 2 0.259204 0.070361 0.044862 11.00000 -1.20000 AFIX 0 C7 1 0.356012 0.183171 -0.127544 11.00000 0.02081 0.01945 = 0.01936 0.00788 0.00661 0.00480 C8 1 0.210242 0.113005 -0.341858 11.00000 0.03406 0.04133 = 0.01941 0.01173 0.00171 0.00256 AFIX 137 H8A 2 0.140146 0.005800 -0.358085 11.00000 -1.50000 H8B 2 0.288193 0.117366 -0.411030 11.00000 -1.50000 H8C 2 0.045896 0.172610 -0.332342 11.00000 -1.50000 AFIX 0 N1 3 0.591626 0.237341 -0.029871 11.00000 0.01570 0.02564 = 0.01975 0.00835 0.00584 -0.00021 AFIX 43 H1 2 0.761811 0.266101 -0.042403 11.00000 -1.20000 AFIX 0 O1 4 0.103577 0.146727 -0.125012 11.00000 0.01589 0.03149 = 0.02433 0.01011 0.00524 0.00099 O2 4 0.440031 0.176496 -0.230434 11.00000 0.02191 0.04020 = 0.01980 0.01518 0.00491 0.00127 CL1 5 0.576214 0.301150 0.479837 11.00000 0.05487 0.03812 = 0.02080 0.01322 0.01223 -0.00522 BR1 6 1.041707 0.507052 0.169043 11.00000 0.02532 0.02146 = 0.02454 0.01045 0.00644 -0.00329 HKLF 4 REM ks1504c in P-1 REM R1 = 0.0239 for 1777 Fo > 4sig(Fo) and 0.0248 for all 1847 data REM 119 parameters refined using 0 restraints END WGHT 0.0400 0.1570 REM Highest difference peak 0.303, deepest hole -0.607, 1-sigma level 0.078 Q1 1 0.8845 0.5112 0.0759 11.00000 0.05 0.30 Q2 1 0.6622 0.3107 0.1422 11.00000 0.05 0.29 Q3 1 1.1989 0.5135 0.2672 11.00000 0.05 0.26 Q4 1 0.7828 0.4854 0.0071 11.00000 0.05 0.25 Q5 1 0.8234 0.3629 0.2626 11.00000 0.05 0.25 Q6 1 0.4238 0.0943 -0.3985 11.00000 0.05 0.25 Q7 1 0.6969 0.2969 0.3066 11.00000 0.05 0.23 Q8 1 1.0674 0.6229 0.2806 11.00000 0.05 0.23 Q9 1 -0.0506 0.3197 -0.3613 11.00000 0.05 0.22 Q10 1 0.6403 0.3491 0.3132 11.00000 0.05 0.22 ; _shelx_res_checksum 23778 _shelxl_version_number .2013 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 C C1 0.5832(4) 0.2508(2) 0.08977(18) 0.0178(4) Uani d 1 C C2 0.7774(4) 0.3658(2) 0.19208(19) 0.0189(4) Uani d 1 C C3 0.7777(5) 0.3806(2) 0.31131(19) 0.0226(4) Uani d 1 H H3 0.9115 0.4585 0.3796 0.027 Uiso calc 1 C C4 0.5803(5) 0.2806(3) 0.3295(2) 0.0242(4) Uani d 1 C C5 0.3866(5) 0.1654(2) 0.2315(2) 0.0230(4) Uani d 1 H H5 0.2525 0.0973 0.2455 0.028 Uiso calc 1 C C6 0.3903(5) 0.1504(2) 0.1125(2) 0.0210(4) Uani d 1 H H6 0.2592 0.0704 0.0449 0.025 Uiso calc 1 C C7 0.3560(5) 0.1832(2) -0.12754(19) 0.0194(4) Uani d 1 C C8 0.2102(6) 0.1130(3) -0.3419(2) 0.0324(5) Uani d 1 H H8A 0.1401 0.0058 -0.3581 0.049 Uiso calc 1 H H8B 0.2882 0.1174 -0.4110 0.049 Uiso calc 1 H H8C 0.0459 0.1726 -0.3323 0.049 Uiso calc 1 N N1 0.5916(4) 0.2373(2) -0.02987(16) 0.0204(3) Uani d 1 H H1 0.7618 0.2661 -0.0424 0.024 Uiso calc 1 O O1 0.1036(3) 0.14673(18) -0.12501(14) 0.0242(3) Uani d 1 O O2 0.4400(3) 0.17650(19) -0.23043(14) 0.0264(3) Uani d 1 Cl Cl1 0.57621(15) 0.30115(7) 0.47984(5) 0.03750(16) Uani d 1 Br Br1 1.04171(4) 0.50705(2) 0.16904(2) 0.02356(10) Uani 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 C1 0.0170(9) 0.0181(9) 0.0196(10) 0.0047(7) 0.0063(7) 0.0075(7) C2 0.0177(9) 0.0181(9) 0.0223(10) 0.0019(7) 0.0058(8) 0.0091(8) C3 0.0241(10) 0.0215(9) 0.0200(10) -0.0003(8) 0.0033(8) 0.0070(8) C4 0.0310(11) 0.0269(11) 0.0194(10) 0.0054(9) 0.0097(8) 0.0121(8) C5 0.0239(10) 0.0219(10) 0.0264(11) 0.0013(8) 0.0099(8) 0.0115(8) C6 0.0202(10) 0.0197(9) 0.0222(10) 0.0002(7) 0.0058(8) 0.0072(8) C7 0.0208(10) 0.0194(9) 0.0194(10) 0.0048(7) 0.0066(8) 0.0079(8) C8 0.0341(12) 0.0413(13) 0.0194(10) 0.0026(10) 0.0017(9) 0.0117(10) N1 0.0157(8) 0.0256(9) 0.0198(8) -0.0002(6) 0.0058(6) 0.0084(7) O1 0.0159(7) 0.0315(8) 0.0243(8) 0.0010(6) 0.0052(6) 0.0101(6) O2 0.0219(8) 0.0402(9) 0.0198(7) 0.0013(6) 0.0049(6) 0.0152(7) Cl1 0.0549(4) 0.0381(3) 0.0208(3) -0.0052(3) 0.0122(2) 0.0132(2) Br1 0.02532(14) 0.02146(14) 0.02454(14) -0.00329(9) 0.00644(9) 0.01045(10) 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' 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' Cl Cl 0.3639 0.7018 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C6 C1 N1 122.34(18) C6 C1 C2 117.59(19) N1 C1 C2 120.06(18) C3 C2 C1 121.46(19) C3 C2 Br1 118.43(15) C1 C2 Br1 120.11(15) C4 C3 C2 119.0(2) C4 C3 H3 120.5 C2 C3 H3 120.5 C5 C4 C3 121.44(19) C5 C4 Cl1 119.54(17) C3 C4 Cl1 119.02(17) C4 C5 C6 119.14(19) C4 C5 H5 120.4 C6 C5 H5 120.4 C5 C6 C1 121.39(19) C5 C6 H6 119.3 C1 C6 H6 119.3 O1 C7 O2 123.82(19) O1 C7 N1 126.17(19) O2 C7 N1 110.00(17) O2 C8 H8A 109.5 O2 C8 H8B 109.5 H8A C8 H8B 109.5 O2 C8 H8C 109.5 H8A C8 H8C 109.5 H8B C8 H8C 109.5 C7 N1 C1 124.53(17) C7 N1 H1 117.7 C1 N1 H1 117.7 C7 O2 C8 115.05(17) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C6 1.400(3) C1 N1 1.401(3) C1 C2 1.404(3) C2 C3 1.384(3) C2 Br1 1.890(2) C3 C4 1.381(3) C3 H3 0.9500 C4 C5 1.381(3) C4 Cl1 1.744(2) C5 C6 1.384(3) C5 H5 0.9500 C6 H6 0.9500 C7 O1 1.214(3) C7 O2 1.345(2) C7 N1 1.354(3) C8 O2 1.439(3) C8 H8A 0.9800 C8 H8B 0.9800 C8 H8C 0.9800 N1 H1 0.8800 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 N1 H1 O1 1_655 0.88 2.19 2.885(2) 135.2 _cod_database_fobs_code 1548681