#------------------------------------------------------------------------------ #$Date: 2022-01-21 05:01:58 +0200 (Fri, 21 Jan 2022) $ #$Revision: 272183 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/24/40/2244017.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_2244017 loop_ _publ_author_name 'Rakhmonova, Dilnoza' 'Kadirova, Zukhra' 'Torambetov, Batirbay' 'Kadirova, Shakhnoza' 'Ashurov, Jamshid' 'Shishkina, Svitlana' _publ_section_title ; The molecular and crystal structures of 2-(3-hydroxypropyl)benzimidazole and its nitrate salt ; _journal_coeditor_code DX2040 _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first ; ; _journal_paper_doi 10.1107/S2056989022000585 _journal_volume 78 _journal_year 2022 _chemical_formula_iupac 'C10 H12 N2 O' _chemical_formula_moiety 'C10 H12 N2 O' _chemical_formula_sum 'C10 H12 N2 O' _chemical_formula_weight 176.22 _chemical_name_systematic ; 2-(3-Hydroxypropyl)-1H-benzimidazole ; _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary difmap _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2016/6 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.852(2) _cell_length_b 12.437(3) _cell_length_c 12.444(3) _cell_measurement_reflns_used 1839 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 32.4 _cell_measurement_theta_min 5.2 _cell_volume 905.7(4) _computing_cell_refinement ; CrysAlisPro (Oxford Diffraction, 2009) ; _computing_data_collection ; CrysAlisPro (Oxford Diffraction, 2009) ; _computing_data_reduction ; CrysAlisPro (Oxford Diffraction, 2009) ; _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material 'OLEX2 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL2016/6 (Sheldrick, 2015)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 10.2576 _diffrn_measured_fraction_theta_full 0.961 _diffrn_measured_fraction_theta_max 0.961 _diffrn_measurement_device_type 'Oxford Diffraction Xcallibur, Ruby' _diffrn_measurement_method '\w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_unetI/netI 0.0276 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 3945 _diffrn_reflns_theta_full 62.021 _diffrn_reflns_theta_max 62.021 _diffrn_reflns_theta_min 5.027 _diffrn_source 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.688 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.958 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysAlisPro; Oxford Diffraction, 2009) ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.292 _exptl_crystal_description block _exptl_crystal_F_000 376 _exptl_crystal_size_max 0.120 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.080 _refine_diff_density_max 0.110 _refine_diff_density_min -0.188 _refine_ls_abs_structure_details ; Flack x determined using 428 quotients [(I^+^)-(I^-^)]/[(I^+^)+(I^-^)] (Parsons et al., 2013) ; _refine_ls_abs_structure_Flack 0.1(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 166 _refine_ls_number_reflns 1371 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.0490 _refine_ls_R_factor_gt 0.0394 _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^)+(0.0573P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0864 _refine_ls_wR_factor_ref 0.0912 _reflns_number_gt 1191 _reflns_number_total 1371 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file dx2040sup1.cif _cod_data_source_block BIZ _cod_database_code 2244017 _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 0.922 _shelx_estimated_absorpt_t_max 0.947 _shelx_hkl_file ; 1 0 0 73.4402 72.2241 1 -1 0 0 51.4148 84.6975 2 1 0 0 56.8237 92.6832 0 2 0 0 55752.5 629.753 1 2 0 0 55238.7 750.671 0 -2 0 0 56550.5 690.784 2 -3 0 0 171.031 288.092 6 -3 0 0 224.949 217.605 2 3 0 0 225.256 302.595 0 -3 0 0 65.6203 280.766 5 -4 0 0 407.333 346.887 5 -4 0 0 421.610 356.575 6 -5 0 0 51.8750 413.912 6 -5 0 0-197.908 379.713 5 -6 0 0 20816.5 1006.84 6 0 1 0 551.278 64.4300 0 1 -1 0 492.510 135.671 0 -1 1 0 889.535 137.938 0 1 1 0 556.257 114.580 2 -1 -1 0 637.593 134.049 2 1 -1 0 472.895 131.385 1 -2 -1 0 75520.3 886.244 2 2 -1 0 71439.8 907.793 0 2 -1 0 75190.1 887.638 1 -2 1 0 73279.6 713.362 2 2 1 0 72291.2 827.422 0 -3 -1 0 25401.5 785.347 6 -3 1 0 25216.3 745.745 5 -3 -1 0 24977.9 720.992 5 -4 1 0 3064.62 459.551 6 -4 -1 0 3419.98 499.988 6 -4 -1 0 3343.69 407.865 5 -4 1 0 3719.93 451.030 5 -5 -1 0 1957.06 522.361 6 -5 1 0 3196.85 599.292 6 -5 -1 0 3275.39 473.065 5 -6 1 0 18814.8 976.796 6 0 -2 0 151011. 903.230 1 0 2 0 148485. 849.881 0 1 2 0 23090.2 458.904 2 1 -2 0 23725.0 467.015 0 1 -2 0 23353.3 482.721 1 -1 2 0 23722.5 469.683 0 -2 2 0 33545.3 459.618 2 2 2 0 34677.4 697.482 2 2 -2 0 32514.3 681.186 0 2 -2 0 33241.5 690.511 1 -3 -2 0 47077.8 1086.55 6 3 -2 0 50476.8 975.819 1 -3 -2 0 51597.2 1014.53 5 -3 2 0 47444.0 1054.84 5 -4 -2 0 10045.9 698.907 6 -4 2 0 9952.24 689.877 6 -4 -2 0 11128.7 652.925 5 -4 2 0 9667.33 639.381 5 -5 -2 0 6192.37 657.249 6 -5 -2 0 7942.46 600.607 5 -5 2 0 6902.76 702.330 6 -6 2 0 1013.06 423.280 6 0 3 0 78.9053 154.139 0 0 -3 0-2.30380 149.552 1 1 -3 0 56942.1 799.259 0 1 3 0 55291.2 775.422 2 -1 -3 0 56027.9 505.449 1 -1 3 0 55639.0 787.187 0 2 3 0 56977.2 948.833 2 2 -3 0 55250.6 936.853 0 2 -3 0 56474.9 1000.20 1 -3 3 0 18361.8 705.208 5 -3 -3 0 20033.6 657.291 5 -3 -3 0 18860.2 765.907 6 -4 -3 0 4684.45 586.349 6 -4 3 0 3935.29 520.672 6 -5 3 0 1723.06 456.860 6 -5 -3 0 2095.10 471.137 5 -6 3 0 5464.48 600.341 6 6 -3 0 4092.39 1047.88 4 0 -4 0 343767. 1983.42 1 0 4 0 337145. 1841.21 0 -1 4 0 91928.6 1107.57 0 -1 -4 0 91364.7 820.792 1 1 -4 0 93168.7 1130.62 0 1 -4 0 94902.0 1217.80 1 1 4 0 93058.0 1118.35 2 2 4 0 82162.8 1217.83 2 2 -4 0 82298.6 1310.68 1 -3 -4 0 138625. 1673.37 5 -4 -4 0 76254.5 1441.41 5 -5 4 0 4169.58 537.575 6 6 -4 0 863.540 972.390 4 -6 4 0 505.887 446.151 6 0 5 0 114.720 187.872 0 0 5 0 89.2014 186.994 2 0 -5 0 245.274 221.306 1 1 5 0 21528.3 511.932 0 1 5 0 21276.3 605.022 2 -1 -5 0 22273.2 490.372 1 1 -5 0 20698.4 674.105 1 -1 5 0 22548.6 635.032 0 -2 -5 0 57177.6 1214.62 12 4 -5 0 1175.15 522.974 9 -5 -5 0 7013.78 592.152 7 -5 5 0 6926.52 640.729 6 -6 5 0-30.9702 450.662 6 6 5 0 430.548 716.220 11 6 -5 0 835.371 894.374 4 0 -6 0 215693. 2711.77 12 0 6 0 220424. 1853.63 2 0 6 0 221870. 1878.48 0 0 -6 0 218835. 2018.02 1 -1 -6 0 137955. 1364.20 1 -1 -6 0 137830. 1981.70 12 -2 -6 0 1099.97 346.031 12 4 -6 0 167.818 468.350 9 -4 -6 0-282.418 345.118 7 -5 -6 0-349.667 460.330 7 -5 6 0-200.496 459.488 6 6 -6 0 1387.98 898.781 4 -6 6 0 2111.79 541.110 6 0 -7 0-142.563 303.031 7 0 -7 0 529.166 405.599 12 0 -7 0-153.856 311.617 8 -1 -7 0 8051.67 638.341 12 1 -7 0 7539.24 497.164 8 -1 -7 0 7334.34 503.739 7 -1 -7 0 7715.39 529.380 8 -2 -7 0 24224.8 906.246 7 -2 -7 0 24767.0 936.447 12 -3 -7 0 544.770 293.757 7 4 -7 0 4159.14 630.614 9 -4 -7 0 3666.02 466.147 7 -5 7 0 4459.91 589.771 6 -5 -7 0 4089.91 495.406 7 5 7 0 4817.52 713.105 11 0 -8 0 2198.47 386.854 8 0 -8 0 2842.23 341.671 7 0 -8 0 2093.64 587.236 12 -1 -8 0 472.537 427.423 8 -1 -8 0 873.206 350.475 12 -1 -8 0 899.186 267.608 7 1 -8 0 44.1745 578.241 12 1 -8 0 914.846 354.827 8 2 -8 0 548.600 329.770 8 -2 -8 0 562.411 295.979 7 -2 -8 0 165.904 366.304 12 -3 -8 0 2149.72 385.349 7 3 -8 0 1584.85 549.917 9 4 -8 0 29983.0 1256.88 9 -4 -8 0 29433.7 1128.48 7 5 -8 0 1477.72 431.510 8 -5 8 0 1433.56 464.472 6 5 -8 0 616.183 907.743 4 -5 -8 0 1509.41 449.473 7 5 8 0 1235.79 523.123 11 0 -9 0-383.226 430.555 12 0 -9 0-231.691 376.401 7 0 -9 0-445.651 427.612 9 0 -9 0 42.4430 394.191 8 1 -9 0 7788.23 603.087 8 -1 -9 0 7864.61 637.800 12 1 -9 0 8519.30 762.473 12 -1 -9 0 7562.83 607.671 7 -1 -9 0 8221.69 627.588 8 2 -9 0 30742.4 1155.58 8 -2 -9 0 31411.6 1140.22 7 -2 -9 0 30604.9 1208.91 12 3 -9 0 11954.6 866.395 9 -3 -9 0 12749.5 797.102 7 3 -9 0 12553.2 800.071 8 4 -9 0 2267.38 544.357 9 -4 -9 0 2867.90 460.508 7 4 -9 0 2110.04 445.195 8 4 9 0 2887.05 609.303 11 5 -9 0 2010.26 384.208 8 -5 9 0 1396.35 562.639 6 5 -9 0 728.132 801.610 4 -5 -9 0 842.009 476.512 7 5 9 0 871.738 553.320 11 0 -10 0 42436.3 1450.80 12 0 -10 0 46556.7 1367.84 8 0 -10 0 44122.8 1305.28 9 0 -10 0 46224.9 1259.19 7 1 -10 0 10744.6 846.333 12 1 -10 0 9983.32 697.753 8 -1 -10 0 9020.73 649.326 7 -1 -10 0 9748.44 739.056 12 -1 -10 0 9966.67 696.687 8 1 -10 0 8943.29 757.877 9 2 -10 0 9747.15 826.989 9 2 -10 0 10128.8 759.156 8 -2 -10 0 10561.0 754.795 7 -2 -10 0 9892.98 755.975 12 2 10 0 11364.1 878.893 11 3 -10 0 5579.34 987.465 4 3 -10 0 6238.51 704.625 9 3 -10 0 5625.24 601.804 8 3 10 0 5637.13 719.800 11 -3 -10 0 6034.50 610.745 7 4 -10 0 785.160 955.929 4 4 -10 0 750.095 533.044 9 4 10 0 580.013 515.834 11 4 -10 0 1000.69 382.081 8 -4 -10 0 266.903 407.965 7 0 -11 0-104.761 480.461 12 0 -11 0-37.2014 548.475 8 -1 -11 0 10915.7 743.562 7 1 -11 0 9623.68 762.236 9 -1 -11 0 10002.1 771.311 12 1 -11 0 10324.6 753.984 8 -2 -11 0 1790.51 428.343 7 2 -11 0 1506.87 542.071 9 2 -11 0 1108.87 457.631 8 3 -11 0-103.007 473.779 9 3 -11 0 279.919 464.208 8 -3 -11 0 349.795 382.938 7 3 11 0-570.770 612.094 11 4 -11 0 2175.73 473.697 9 4 -11 0 2041.17 432.369 8 4 11 0 1669.45 569.523 11 -4 -11 0 2050.94 452.111 7 0 -12 0 81447.3 1863.80 12 1 -12 0 1337.40 564.820 8 -1 -12 0 1393.04 502.710 7 -1 -12 0 1751.93 431.830 12 1 -12 0 1606.13 570.586 9 2 -12 0-351.725 480.747 9 2 -12 0 76.8245 522.375 8 -2 -12 0-113.714 417.534 7 3 -12 0 1244.12 489.610 9 3 -12 0 1922.41 504.995 8 -3 -12 0 1670.02 454.650 7 1 -13 0 1344.55 671.238 9 2 -13 0 4191.07 505.591 9 2 -13 0 4442.96 695.107 8 -2 -13 0 3829.94 504.714 7 1 0 -1 6008.62 156.551 2 -1 0 1 5990.68 164.069 0 -1 0 -1 5716.98 193.104 1 1 0 -1 6157.40 158.623 0 2 0 -1 40988.2 545.724 1 2 0 1 39029.0 714.345 0 -2 0 -1 40495.9 653.133 2 2 0 -1 39463.9 561.764 0 -3 0 -1 102.310 233.458 5 3 0 1 580.346 354.584 0 -3 0 1 92.2076 308.968 6 -3 0 1 222.493 295.907 5 -3 0 -1-200.547 246.072 2 -3 0 -1-247.966 269.715 6 -4 0 1 8663.84 568.865 5 -4 0 -1 7219.51 584.506 6 -4 0 -1 9077.00 608.582 5 -4 0 1 8791.02 651.109 6 -5 0 -1 9446.22 814.200 6 -5 0 -1 7999.62 688.193 5 -5 0 1 9350.69 764.938 6 -6 0 1 2928.31 497.933 6 0 -1 1 535.479 71.2474 0 0 -1 -1 527.530 69.7478 2 0 1 -1 698.333 105.352 1 1 -1 1 127986. 999.360 1 1 -1 1 128417. 984.056 0 1 -1 -1 129467. 859.984 0 -1 1 1 129315. 862.216 0 1 1 -1 128713. 870.243 2 -1 1 -1 126175. 958.934 1 -1 -1 -1 126927. 950.081 2 -2 -1 -1 17994.8 473.010 2 2 1 -1 18163.1 341.611 0 2 -1 -1 18636.9 450.236 1 2 1 -1 17906.2 264.847 1 2 -1 -1 18073.7 447.530 0 2 -1 1 17194.0 514.396 0 2 -1 1 18341.6 480.178 1 -2 1 -1 17786.1 438.772 2 -3 1 1 41823.6 960.960 5 -3 -1 -1 42450.7 973.995 5 -3 -1 1 43556.2 904.077 5 -3 -1 1 42430.8 996.032 6 -3 -1 -1 41859.3 1023.75 6 -3 1 -1 41038.4 1000.79 6 -3 1 -1 42216.6 974.359 5 -3 1 -1 42760.1 760.743 2 -3 -1 -1 41826.6 839.306 2 3 -1 -1 42364.7 852.935 0 -4 -1 -1 27018.0 1004.96 6 -4 1 1 26489.1 939.728 5 -4 -1 -1 27288.9 957.506 5 -4 1 -1 25990.4 968.131 5 -4 1 1 26653.6 1004.41 6 -4 1 -1 25474.4 960.762 6 -4 -1 1 26017.3 982.191 6 -4 -1 1 28222.8 911.983 5 -5 1 1 875.379 425.241 6 5 -1 1 1503.63 920.640 4 -5 -1 -1 678.015 514.821 6 -5 -1 1 1403.46 434.212 5 -5 -1 -1 1733.25 394.516 5 -5 -1 1 1426.23 442.521 6 -5 1 -1 965.421 428.465 5 -5 1 -1 1465.66 473.029 6 6 -1 1 3688.41 801.950 3 -6 1 1 2653.93 484.835 6 -6 1 -1 3556.16 582.901 6 0 -2 -1 739825. 7517.65 2 0 -2 1 732067. 2250.69 1 0 2 -1 723294. 7241.09 0 0 2 1 733160. 7341.49 2 0 2 -1 732487. 2207.62 1 1 2 -1 356816. 1720.22 2 -1 2 1 354992. 1694.58 0 1 -2 1 357009. 1797.94 0 1 2 -1 348605. 1104.98 1 -1 -2 -1 361392. 1779.26 2 1 2 -1 352025. 3211.25 0 1 2 1 354472. 1776.24 2 -1 2 -1 356959. 1842.65 1 1 -2 1 355489. 1925.01 1 -2 2 1 77305.5 988.792 0 2 2 -1 75919.5 588.482 0 -2 -2 -1 78431.8 1030.27 2 2 -2 -1 78835.5 1032.41 1 2 -2 1 75234.4 1057.19 1 2 -2 -1 74328.2 964.359 0 2 -2 1 74205.2 1048.42 0 2 2 -1 76223.9 978.689 2 -3 2 -1 57861.5 1187.07 5 3 -2 -1 60820.6 1086.90 0 -3 -2 -1 60451.7 1161.48 5 -3 -2 1 58621.9 1185.63 6 -3 -2 1 61003.7 1030.37 5 -3 2 1 58261.1 1169.94 5 -3 -2 -1 57565.2 1210.99 6 -4 -2 1 6144.19 610.358 6 -4 -2 -1 5517.10 594.224 6 -4 -2 -1 6194.02 530.635 5 -4 -2 1 6916.81 497.160 5 -4 2 -1 6068.79 534.296 5 -4 2 1 5484.27 562.234 6 -4 2 -1 7100.65 580.933 6 -5 2 1 7224.16 718.610 6 5 2 1 9079.03 678.850 11 -5 2 -1 7483.96 661.129 6 -5 -2 -1 8808.31 660.754 5 -5 -2 1 6925.88 706.388 6 -5 -2 1 8871.88 636.480 5 -6 2 -1 4666.16 599.534 6 6 2 1 4100.70 601.017 10 -6 2 1 4660.92 622.356 6 0 3 -1 438805. 1956.89 1 0 3 -1 438181. 1732.35 0 0 -3 1 442051. 1758.44 0 0 -3 1 443336. 2080.35 1 -1 3 1 37686.4 380.260 2 -1 3 1 38154.5 671.681 0 1 3 -1 36590.5 662.962 2 1 3 -1 38061.4 404.869 0 -1 3 -1 38333.8 669.391 0 1 3 1 38198.8 661.142 2 -1 -3 -1 37723.5 672.269 2 1 -3 1 37212.7 733.114 1 1 -3 1 39125.4 688.790 0 2 -3 1 4762.92 345.436 0 2 3 -1 5898.42 344.906 2 -2 -3 -1 5773.36 373.431 2 2 -3 -1 5633.52 365.162 1 2 3 1 5585.84 341.368 2 2 -3 -1 5500.08 327.957 0 2 -3 1 5046.54 365.970 1 -2 3 1 4614.85 331.814 0 -3 -3 -1 12659.2 604.815 5 -3 -3 1 12855.2 626.335 6 -3 -3 -1 11183.1 636.889 6 3 -3 1 12326.7 595.878 9 -3 3 -1 12838.7 629.867 5 -4 3 -1 24141.8 962.870 5 -4 -3 -1 26503.4 935.419 5 -4 -3 1 24457.4 994.032 6 -4 3 -1 25901.8 1030.56 6 -5 3 1 41.9872 420.457 6 -5 3 -1 474.987 462.847 6 5 3 1 765.122 556.540 11 -5 -3 -1 291.871 446.416 5 6 -3 -1-1244.51 1116.23 4 6 3 1 28.1728 542.397 10 -6 3 1-94.7115 463.696 6 -6 3 -1 150.840 464.180 6 0 4 1 125692. 1180.87 0 0 4 1 128047. 1100.30 2 0 4 -1 128981. 1112.76 0 -1 4 -1 63052.2 940.648 0 -1 4 1 61494.6 918.957 0 1 -4 1 62064.1 1035.28 1 1 -4 1 62559.3 934.088 0 1 4 -1 63623.5 950.336 2 -1 4 1 64133.5 635.049 2 -1 -4 -1 62303.6 693.445 1 1 4 -1 62518.1 656.082 0 1 4 1 64411.4 947.813 2 -2 -4 -1 10586.7 533.867 12 2 4 -1 11026.5 477.875 2 -3 -4 -1 12337.9 607.699 5 3 -4 1 11928.9 656.093 9 -4 -4 -1 2000.37 396.428 5 -4 -4 1 2010.60 359.446 7 -5 4 -1 871.816 385.595 6 -5 4 1 895.134 404.715 6 -5 -4 -1 667.262 472.061 5 5 4 1 1350.94 530.031 11 6 -4 1 1251.05 949.147 4 -6 4 -1 1279.17 453.433 6 6 -4 -1 328.730 991.078 4 -6 4 1 1036.25 474.855 6 0 -5 1 13335.3 497.300 1 0 -5 -1 13469.9 486.127 1 0 5 -1 13690.7 445.046 0 0 5 1 12962.8 423.176 2 0 5 1 12662.5 459.879 0 -1 -5 1 22196.7 508.022 1 1 -5 -1 22931.5 687.714 1 1 -5 1 22103.0 702.206 1 -1 5 1 22260.1 638.510 0 -1 5 1 22399.9 454.373 2 1 5 -1 23771.4 482.925 0 1 -5 1 22741.2 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3 5 9 21525.4 964.131 13 -3 -5 -9 19770.9 979.412 5 3 5 9 20520.0 983.951 3 3 -5 9 22594.9 978.373 3 3 -5 9 20596.0 1028.81 4 4 5 9 5581.28 581.684 13 -4 -5 -9 6099.81 581.397 5 4 -5 9 6590.03 589.694 3 4 -5 9 6718.51 593.214 4 0 6 9 7765.40 633.743 14 -1 6 9 14409.5 824.684 14 1 6 9 14603.8 820.903 14 1 -6 -9 16944.5 880.546 8 1 -6 9 14131.3 796.894 4 -2 6 9 1302.59 454.480 14 2 6 9 1587.86 491.523 14 2 -6 9 2434.27 463.415 4 3 -6 9 1482.11 437.460 4 3 6 9 1033.86 506.505 13 -3 -6 -9 1307.22 446.854 5 4 6 9 9369.86 640.487 13 -4 -6 -9 9210.70 663.958 5 4 -6 9 11088.1 702.507 4 0 7 9 716.930 382.479 14 -1 7 9 6306.66 633.176 14 1 7 9 6254.84 604.720 14 -1 -7 -9 7535.78 827.835 12 1 -7 -9 8756.23 669.965 8 1 -7 9 7212.51 610.574 4 -2 7 9 21479.0 936.844 14 2 7 9 21250.4 955.472 14 2 -7 9 20706.9 972.411 4 3 -7 9 3879.18 502.519 4 3 7 9 2549.21 603.141 13 -3 -7 -9 3603.18 556.692 5 -4 -7 -9 6415.49 514.410 5 4 -7 9 7130.06 549.207 4 0 8 9-207.549 385.424 14 0 -8 -9 1753.91 883.740 12 -1 8 9 2451.81 494.333 14 1 8 9 1884.46 418.679 14 -1 -8 -9 1777.93 678.810 12 1 -8 -9 2504.23 525.891 8 -2 8 9 1909.76 508.648 14 2 8 9 1254.80 538.546 14 2 -8 9 1287.30 463.783 4 3 -8 9-400.005 427.466 4 -3 -8 -9 124.578 457.902 5 0 9 9 620.862 440.973 14 0 -9 -9-38.1511 776.438 12 -1 9 9 12500.0 808.147 14 1 9 9 10923.9 735.139 14 -1 -9 -9 12283.4 919.670 12 -2 9 9 3493.10 572.125 14 2 9 9 3992.01 575.890 14 2 -9 9 4174.48 572.963 4 2 -9 -9 4079.90 669.154 8 -3 -9 -9-195.811 444.235 5 0 10 9 693.926 440.256 14 0 -10 -9-167.329 681.643 12 -1 10 9 2210.03 422.819 14 1 10 9 2915.18 445.953 14 -1 -10 -9 2757.78 654.751 12 1 -10 -9 3678.16 802.770 12 2 -10 -9 909.373 865.786 12 1 0 10 726.292 397.818 3 2 0 10 25774.7 1084.50 3 3 0 10 2335.18 497.149 3 4 0 10-423.733 354.175 3 -4 0 -10-1087.67 523.339 5 1 1 10 9304.45 669.041 3 1 -1 10 11151.1 707.065 3 -2 1 10 27723.7 1061.81 14 2 1 10 26998.7 1030.51 14 2 1 10 24472.7 1065.49 3 2 -1 10 27061.2 1084.17 3 2 -1 10 28357.9 1148.92 4 3 1 10 2767.07 506.739 3 3 -1 10 2763.48 513.914 3 3 -1 10 2050.60 449.237 4 3 1 10 2903.26 523.810 13 -3 -1 -10 3495.26 485.630 5 4 1 10 2914.98 416.560 3 4 -1 10 2846.95 454.809 3 -4 -1 -10 2793.59 468.571 5 -1 2 10 6011.90 559.964 14 1 2 10 6376.11 585.683 14 1 2 10 5908.86 627.799 3 1 -2 10 6394.11 579.425 3 2 -2 10 487.540 391.066 3 2 -2 10 644.332 404.264 4 -2 2 10 113.238 474.284 14 2 2 10 652.338 423.950 14 2 2 10 194.577 467.542 13 -2 -2 -10 966.451 472.920 5 2 2 10-20.5869 373.220 3 3 -2 10 3282.74 499.268 3 3 -2 10 2684.57 525.952 4 3 2 10 3477.85 533.042 13 -3 -2 -10 2914.27 450.439 5 3 2 10 2462.33 502.407 3 4 -2 10 1177.45 429.218 3 4 -2 10 1500.61 473.949 4 4 2 10 471.245 442.470 13 -4 -2 -10-65.5788 460.426 5 4 2 10 856.262 427.102 3 0 3 10 12041.8 758.862 14 -1 3 10 10290.8 768.185 14 1 3 10 9387.12 669.009 14 1 -3 10 11433.9 686.198 3 2 -3 10 4935.03 565.735 3 -2 3 10 5113.97 564.930 14 2 3 10 5209.13 545.474 14 2 -3 10 4744.60 618.734 4 2 3 10 4313.58 561.888 13 -2 -3 -10 5110.90 573.414 5 2 3 10 5711.89 617.064 3 3 -3 10 1056.44 475.719 3 3 -3 10-30.1197 417.323 4 3 3 10 1460.76 491.047 13 -3 -3 -10 582.530 485.383 5 3 3 10 1111.44 386.918 3 4 -3 10 493.810 408.176 3 4 -3 10-707.388 437.000 4 4 3 10 624.007 457.858 13 -4 -3 -10-638.527 447.825 5 4 3 10 275.030 412.640 3 0 4 10 3243.95 470.679 14 -1 4 10 17228.7 877.790 14 1 4 10 15969.6 849.714 14 -2 4 10 11871.9 758.506 14 2 4 10 10961.6 721.934 14 2 4 10 11593.9 715.423 13 2 -4 10 12021.4 697.032 3 2 -4 10 10730.7 782.921 4 3 -4 10 1186.17 470.999 3 3 -4 10 909.847 421.671 4 3 4 10 870.168 479.444 13 -3 -4 -10 779.770 403.949 5 3 4 10 498.508 409.933 3 4 -4 10 3117.01 504.756 3 4 -4 10 2774.82 440.629 4 4 4 10 2366.78 438.965 13 4 4 10 2285.25 491.248 3 -4 -4 -10 2512.19 418.379 5 0 5 10 5919.46 632.460 14 -1 5 10 5858.51 592.943 14 1 5 10 4786.38 545.157 14 -2 5 10 12475.7 770.830 14 2 5 10 12052.6 700.443 14 2 -5 10 12622.9 830.123 4 3 -5 10 2169.73 478.279 4 3 5 10 2005.11 549.315 13 -3 -5 -10 2392.79 445.773 5 4 -5 10 1861.76 416.843 4 4 5 10 1798.62 503.773 13 -4 -5 -10 1079.59 418.360 5 0 6 10 2148.34 448.409 14 -1 6 10 1297.77 490.735 14 1 6 10 1728.19 450.322 14 -2 6 10 6732.74 632.800 14 2 6 10 7258.15 592.846 14 2 -6 10 5664.02 611.460 4 3 -6 10 26.6077 431.517 4 -3 -6 -10 1190.27 479.435 5 0 7 10 3365.14 521.087 14 0 -7 -10 2570.78 914.781 12 -1 7 10 756.341 448.917 14 1 7 10-471.624 415.723 14 2 -7 10 2575.10 495.180 4 -2 7 10 2758.48 553.994 14 2 7 10 2502.59 501.602 14 3 -7 10 2039.83 462.798 4 -3 -7 -10 2223.69 448.909 5 0 8 10 164.761 443.383 14 0 -8 -10 1996.51 884.408 12 -1 8 10 6489.84 597.277 14 1 8 10 5124.47 580.727 14 -2 8 10 7059.60 582.976 14 2 8 10 8087.29 605.860 14 0 9 10 2114.82 455.299 14 0 -9 -10 2492.24 760.634 12 -1 9 10 637.895 428.298 14 1 9 10 943.740 425.531 14 1 -9 -10 838.498 847.649 12 2 -9 -10 4530.08 950.188 12 -2 -9 -10 3054.33 468.270 5 0 10 10 573.083 492.652 14 1 0 11 932.964 399.093 3 2 0 11 373.140 414.131 3 3 0 11 10577.6 735.952 3 4 0 11 299.570 401.437 3 1 -1 11 4040.47 546.489 3 -2 1 11 14961.0 854.820 14 2 1 11 13606.8 760.358 14 2 1 11 12821.1 814.258 3 2 -1 11 13881.6 819.634 3 3 -1 11 4972.08 614.857 3 3 1 11 4212.06 550.810 3 4 1 11 1530.36 401.434 3 4 -1 11 1368.98 441.143 3 0 2 11 4633.06 585.253 14 -1 2 11 4299.93 542.471 14 1 2 11 4018.66 495.808 14 1 -2 11 5058.77 572.059 3 2 2 11 16134.9 812.426 14 2 2 11 14356.8 871.054 3 2 -2 11 15854.7 858.906 3 -3 -2 -11 3954.44 553.952 5 3 2 11 3140.48 485.362 3 3 -2 11 3172.62 492.026 3 4 2 11 23.3234 439.891 3 4 -2 11-915.768 463.019 3 0 3 11 6715.58 667.426 14 -1 3 11 8943.45 739.586 14 1 3 11 8502.85 677.192 14 -2 3 11 1042.74 500.854 14 2 3 11 1493.26 480.407 14 -2 -3 -11 143.777 559.760 5 2 -3 11 766.501 493.609 3 3 3 11 2441.88 435.095 3 -3 -3 -11 1368.35 508.897 5 3 -3 11 985.025 467.315 3 0 4 11 696.575 403.991 14 -1 4 11 5127.09 591.873 14 1 4 11 4545.20 545.659 14 -2 4 11 820.969 519.163 14 2 4 11 1030.51 490.023 14 -2 -4 -11 1397.49 504.824 5 -3 -4 -11 705.108 493.820 5 3 -4 11 1153.60 558.340 3 0 5 11 11402.1 776.269 14 -1 5 11 10356.4 781.426 14 1 5 11 9526.26 680.405 14 -2 5 11 487.534 501.586 14 2 5 11-293.388 508.407 14 -2 -5 -11 264.715 464.113 5 -3 -5 -11 1888.80 495.279 5 0 6 11 1241.33 463.315 14 1 6 11 5046.12 523.219 14 -1 6 11 3917.62 504.235 14 -2 6 11 2808.34 533.637 14 2 6 11 3668.59 543.938 14 -2 -6 -11 3456.36 501.212 5 -3 -6 -11 208.160 467.186 5 0 7 11 4216.63 557.361 14 -1 7 11 1068.97 431.894 14 1 7 11 697.114 445.630 14 -2 7 11 10615.8 642.692 14 2 7 11 9381.79 601.244 14 -2 -7 -11 9480.18 598.260 5 0 8 11 379.819 445.283 14 -1 8 11 1923.96 440.250 14 1 8 11 3229.58 419.922 14 1 -8 -11 3051.17 1013.32 12 0 9 11 5855.87 535.320 14 -2 0 12-344.731 494.369 14 2 0 12-721.948 516.791 14 3 0 12 1449.90 443.518 3 0 1 12 5387.42 575.147 14 -1 1 12 3343.48 535.911 14 1 1 12 2500.09 451.754 14 -2 1 12 4276.51 511.927 14 2 1 12 4246.88 502.805 14 -2 -1 12 4389.54 503.168 14 2 -1 12 2778.71 506.929 14 2 -1 12 2987.66 491.848 3 3 1 12 2100.49 405.738 3 3 -1 12 1065.26 483.753 3 0 2 12 373.780 434.592 14 -1 2 12 18989.1 940.539 14 1 2 12 18800.0 913.312 14 -2 2 12 1396.25 528.367 14 2 2 12 711.352 497.830 14 2 -2 12-384.311 521.805 3 3 -2 12 659.794 474.375 3 0 3 12 3814.19 505.427 14 -1 3 12 2943.80 522.575 14 1 3 12 2137.80 406.905 14 -2 3 12 6510.26 553.589 14 2 3 12 6297.42 531.202 14 0 4 12 1878.61 424.362 14 -1 4 12 1105.41 464.336 14 1 4 12 439.752 411.595 14 -2 4 12 1117.46 569.701 14 2 4 12 758.005 525.116 14 0 5 12 4954.73 543.787 14 -1 5 12 1772.52 454.683 14 1 5 12 1391.49 447.448 14 -2 5 12 1418.85 613.671 14 2 5 12 1330.98 584.974 14 -2 -5 -12 3179.62 635.611 5 0 6 12 332.514 398.489 14 -1 6 12 2069.03 470.560 14 1 6 12 1660.73 409.476 14 -1 -6 -12 2322.89 644.049 5 0 7 12 5555.94 514.644 14 -1 7 12 6434.49 554.957 14 1 7 12 6946.87 518.787 14 0 0 13 180.279 382.154 14 -1 0 13 9663.03 641.018 14 1 0 13 8818.26 601.473 14 -2 0 13 804.235 612.690 14 2 0 13 1842.75 543.171 14 0 1 13 2586.13 472.203 14 -1 1 13 932.276 443.970 14 1 1 13 512.918 448.921 14 -2 1 13 2835.87 600.004 14 2 1 13 2593.00 583.808 14 -2 -1 13 2430.41 612.086 14 2 -1 13 2570.72 562.627 14 0 2 13-65.5053 444.297 14 -1 2 13 330.838 432.382 14 1 2 13 274.624 445.904 14 0 3 13 28265.5 1023.48 14 -1 3 13 2202.92 466.265 14 1 3 13 1908.57 415.969 14 0 4 13 325.915 432.400 14 -1 4 13 1935.47 425.963 14 1 4 13 1880.22 408.587 14 0 5 13-548.668 382.543 14 -1 5 13 5625.12 511.101 14 1 5 13 6687.97 491.472 14 0 0 14 2283.28 464.743 14 -1 0 14 911.705 443.366 14 1 0 14 616.709 476.346 14 0 1 14-232.334 452.973 14 0 -1 14-1.65437 472.154 14 0 2 14 821.923 469.266 14 0 -2 14 201.530 450.929 14 0 0 0 0.00 0.00 0 ; _shelx_hkl_checksum 68265 _shelx_res_file ; TITL himfak_6 in P2(1)2(1)2(1) him6.res created by SHELXL-2016/6 at 13:29:37 on 16-Nov-2021 CELL 1.54178 5.852 12.437 12.444 90 90 90 ZERR 4 0 0 0 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,-Z SYMM -X,0.5+Y,0.5-Z SFAC C H O N UNIT 40 48 4 8 EQIV $1 0.5+X,0.5-Y,1-Z EQIV $2 0.5-X,1-Y,0.5+Z EQIV $3 0.5+X,0.5-Y,-Z L.S. 14 PLAN 1 SIZE 0.12 0.1 0.08 HTAB N2 O1_$1 HTAB O1 N1_$2 HTAB C3 C3_$3 CONF MORE -1 BOND $H fmap 2 acta REM REM REM WGHT 0.057300 FVAR 12.91558 O1 3 -0.026119 0.388551 0.582406 11.00000 0.09556 0.04012 = 0.05469 0.00414 0.02024 0.01400 H1 2 -0.080263 0.438933 0.621146 11.00000 0.08275 N1 4 0.647103 0.437189 0.204706 11.00000 0.05265 0.04249 = 0.04573 0.00340 -0.00318 -0.00183 N2 4 0.627126 0.290106 0.305626 11.00000 0.05180 0.03979 = 0.04538 0.00910 -0.00323 -0.00465 H2N 2 0.586945 0.242748 0.349699 11.00000 0.04500 C1 1 0.820425 0.366807 0.174190 11.00000 0.04755 0.04274 = 0.04590 -0.00403 -0.00348 -0.00526 C2 1 0.987810 0.376613 0.096155 11.00000 0.06374 0.05165 = 0.05218 -0.00315 0.00449 -0.01314 H2 2 0.993811 0.443921 0.051103 11.00000 0.06795 C3 1 1.143002 0.294161 0.084678 11.00000 0.06009 0.06580 = 0.06351 -0.01560 0.01013 -0.01043 H3 2 1.268176 0.296566 0.033847 11.00000 0.07562 C4 1 1.133479 0.203652 0.149927 11.00000 0.05530 0.05684 = 0.07260 -0.01597 -0.00133 0.00390 H4 2 1.232296 0.147568 0.144223 11.00000 0.08135 C5 1 0.968300 0.191494 0.227686 11.00000 0.05939 0.04420 = 0.06280 -0.00273 -0.00815 0.00221 H5 2 0.960783 0.128023 0.273626 11.00000 0.07497 C6 1 0.809605 0.274481 0.237691 11.00000 0.04653 0.04253 = 0.04484 -0.00254 -0.00594 -0.00588 C7 1 0.536519 0.387535 0.282981 11.00000 0.04681 0.04040 = 0.04089 -0.00071 -0.00729 -0.00428 C8 1 0.331683 0.433069 0.336999 11.00000 0.05511 0.05086 = 0.04548 0.00334 -0.00490 0.00220 H8A 2 0.368865 0.511310 0.352691 11.00000 0.07604 H8B 2 0.206399 0.430607 0.285734 11.00000 0.05898 C9 1 0.255457 0.379985 0.440346 11.00000 0.05794 0.04175 = 0.04578 -0.00231 -0.00234 0.00182 H9A 2 0.375602 0.381583 0.492881 11.00000 0.05540 H9B 2 0.220483 0.306978 0.427797 11.00000 0.04919 C10 1 0.046696 0.434871 0.484407 11.00000 0.06142 0.04411 = 0.04667 0.00352 -0.00084 0.00302 H10A 2 0.073071 0.511979 0.495214 11.00000 0.05073 H10B 2 -0.085771 0.431986 0.431871 11.00000 0.06852 HKLF 4 REM himfak_6 in P2(1)2(1)2(1) REM R1 = 0.0394 for 1191 Fo > 4sig(Fo) and 0.0490 for all 1371 data REM 166 parameters refined using 0 restraints END WGHT 0.0576 0.0000 REM Highest difference peak 0.110, deepest hole -0.188, 1-sigma level 0.042 Q1 1 1.5016 0.1355 0.2391 11.00000 0.05 0.11 ; _shelx_res_checksum 69217 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' 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 -0.0261(5) 0.38855(16) 0.5824(2) 0.0635(7) Uani d 1 . . H H1 -0.080(6) 0.439(3) 0.621(3) 0.083(14) Uiso d 1 . . N N1 0.6471(4) 0.43719(19) 0.2047(2) 0.0470(6) Uani d 1 . . N N2 0.6271(4) 0.2901(2) 0.3056(2) 0.0457(7) Uani d 1 . . H H2N 0.587(5) 0.243(2) 0.350(3) 0.045(9) Uiso d 1 . . C C1 0.8204(5) 0.3668(2) 0.1742(2) 0.0454(7) Uani d 1 . . C C2 0.9878(6) 0.3766(3) 0.0962(3) 0.0559(9) Uani d 1 . . H H2 0.994(6) 0.444(3) 0.051(3) 0.068(10) Uiso d 1 . . C C3 1.1430(6) 0.2942(3) 0.0847(3) 0.0631(9) Uani d 1 . . H H3 1.268(7) 0.297(3) 0.034(3) 0.076(11) Uiso d 1 . . C C4 1.1335(6) 0.2037(3) 0.1499(3) 0.0616(10) Uani d 1 . . H H4 1.232(6) 0.148(3) 0.144(3) 0.081(12) Uiso d 1 . . C C5 0.9683(6) 0.1915(3) 0.2277(3) 0.0555(9) Uani d 1 . . H H5 0.961(6) 0.128(3) 0.274(3) 0.075(11) Uiso d 1 . . C C6 0.8096(5) 0.2745(2) 0.2377(2) 0.0446(7) Uani d 1 . . C C7 0.5365(5) 0.3875(2) 0.2830(2) 0.0427(7) Uani d 1 . . C C8 0.3317(6) 0.4331(3) 0.3370(3) 0.0505(8) Uani d 1 . . H H8A 0.369(6) 0.511(3) 0.353(3) 0.076(11) Uiso d 1 . . H H8B 0.206(6) 0.431(3) 0.286(3) 0.059(9) Uiso d 1 . . C C9 0.2555(6) 0.3800(3) 0.4403(3) 0.0485(8) Uani d 1 . . H H9A 0.376(6) 0.382(3) 0.493(3) 0.055(9) Uiso d 1 . . H H9B 0.220(5) 0.307(3) 0.428(3) 0.049(8) Uiso d 1 . . C C10 0.0467(6) 0.4349(3) 0.4844(3) 0.0507(8) Uani d 1 . . H H10A 0.073(5) 0.512(3) 0.495(3) 0.051(8) Uiso d 1 . . H H10B -0.086(6) 0.432(3) 0.432(3) 0.069(10) 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 0.0956(18) 0.0401(12) 0.0547(14) 0.0140(12) 0.0202(13) 0.0041(11) N1 0.0527(15) 0.0425(12) 0.0457(15) -0.0018(11) -0.0032(13) 0.0034(11) N2 0.0518(15) 0.0398(13) 0.0454(16) -0.0046(11) -0.0032(12) 0.0091(12) C1 0.0476(17) 0.0427(15) 0.0459(18) -0.0053(14) -0.0035(14) -0.0040(13) C2 0.064(2) 0.0517(18) 0.052(2) -0.0131(17) 0.0045(16) -0.0032(16) C3 0.060(2) 0.066(2) 0.064(2) -0.0104(18) 0.0101(19) -0.016(2) C4 0.055(2) 0.057(2) 0.073(3) 0.0039(17) -0.0013(18) -0.0160(19) C5 0.059(2) 0.0442(17) 0.063(2) 0.0022(15) -0.0082(18) -0.0027(17) C6 0.0465(16) 0.0425(15) 0.0448(18) -0.0059(13) -0.0059(14) -0.0025(13) C7 0.0468(16) 0.0404(14) 0.0409(16) -0.0043(13) -0.0073(14) -0.0007(13) C8 0.0551(18) 0.0509(17) 0.0455(18) 0.0022(16) -0.0049(16) 0.0033(14) C9 0.058(2) 0.0418(18) 0.046(2) 0.0018(14) -0.0023(15) -0.0023(15) C10 0.0614(19) 0.0441(17) 0.0467(19) 0.0030(16) -0.0008(17) 0.0035(15) 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' O O 0.0492 0.0322 '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' 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 C10 O1 H1 . . 107(3) ? C7 N1 C1 . . 105.3(2) ? C7 N2 C6 . . 107.6(3) ? C7 N2 H2N . . 131(2) ? C6 N2 H2N . . 121(2) ? C2 C1 N1 . . 130.6(3) ? C2 C1 C6 . . 120.1(3) ? N1 C1 C6 . . 109.3(3) ? C3 C2 C1 . . 118.3(3) ? C3 C2 H2 . . 123(2) ? C1 C2 H2 . . 119(2) ? C2 C3 C4 . . 121.1(4) ? C2 C3 H3 . . 123(2) ? C4 C3 H3 . . 116(2) ? C5 C4 C3 . . 121.9(4) ? C5 C4 H4 . . 115(2) ? C3 C4 H4 . . 123(2) ? C4 C5 C6 . . 116.7(3) ? C4 C5 H5 . . 122(2) ? C6 C5 H5 . . 121(2) ? N2 C6 C5 . . 132.6(3) ? N2 C6 C1 . . 105.5(3) ? C5 C6 C1 . . 121.9(3) ? N1 C7 N2 . . 112.3(3) ? N1 C7 C8 . . 123.4(3) ? N2 C7 C8 . . 124.3(3) ? C7 C8 C9 . . 117.1(3) ? C7 C8 H8A . . 106(2) ? C9 C8 H8A . . 109(2) ? C7 C8 H8B . . 107(2) ? C9 C8 H8B . . 109(2) ? H8A C8 H8B . . 109(3) ? C10 C9 C8 . . 110.6(3) ? C10 C9 H9A . . 109.7(19) ? C8 C9 H9A . . 111(2) ? C10 C9 H9B . . 108.7(19) ? C8 C9 H9B . . 110.1(19) ? H9A C9 H9B . . 107(3) ? O1 C10 C9 . . 112.0(3) ? O1 C10 H10A . . 109.1(19) ? C9 C10 H10A . . 111.5(19) ? O1 C10 H10B . . 108(2) ? C9 C10 H10B . . 112(2) ? H10A C10 H10B . . 104(3) ? 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 C10 . 1.414(4) ? O1 H1 . 0.85(4) ? N1 C7 . 1.322(4) ? N1 C1 . 1.393(4) ? N2 C7 . 1.352(4) ? N2 C6 . 1.376(4) ? N2 H2N . 0.84(3) ? C1 C2 . 1.385(4) ? C1 C6 . 1.395(4) ? C2 C3 . 1.377(5) ? C2 H2 . 1.01(4) ? C3 C4 . 1.389(5) ? C3 H3 . 0.97(4) ? C4 C5 . 1.376(5) ? C4 H4 . 0.91(4) ? C5 C6 . 1.394(4) ? C5 H5 . 0.98(4) ? C7 C8 . 1.486(5) ? C8 C9 . 1.513(4) ? C8 H8A . 1.02(4) ? C8 H8B . 0.97(3) ? C9 C10 . 1.503(5) ? C9 H9A . 0.96(4) ? C9 H9B . 0.94(3) ? C10 H10A . 0.98(3) ? C10 H10B . 1.01(4) ? 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 N2 H2N O1 3_556 0.84(3) 1.95(3) 2.772(3) 165(3) O1 H1 N1 2_565 0.85(4) 1.90(4) 2.741(3) 169(4) C3 H3 C3 3 0.97(4) 2.87(4) 3.770(4) 154(3) 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 C7 N1 C1 C2 . . . . 179.9(3) ? C7 N1 C1 C6 . . . . -0.5(3) ? N1 C1 C2 C3 . . . . 178.5(3) ? C6 C1 C2 C3 . . . . -1.0(4) ? C1 C2 C3 C4 . . . . -0.4(5) ? C2 C3 C4 C5 . . . . 0.8(5) ? C3 C4 C5 C6 . . . . 0.2(5) ? C7 N2 C6 C5 . . . . 177.5(3) ? C7 N2 C6 C1 . . . . -0.3(3) ? C4 C5 C6 N2 . . . . -179.1(3) ? C4 C5 C6 C1 . . . . -1.7(5) ? C2 C1 C6 N2 . . . . -179.9(3) ? N1 C1 C6 N2 . . . . 0.5(3) ? C2 C1 C6 C5 . . . . 2.1(4) ? N1 C1 C6 C5 . . . . -177.5(3) ? C1 N1 C7 N2 . . . . 0.3(3) ? C1 N1 C7 C8 . . . . -177.9(3) ? C6 N2 C7 N1 . . . . 0.0(3) ? C6 N2 C7 C8 . . . . 178.2(3) ? N1 C7 C8 C9 . . . . -166.7(3) ? N2 C7 C8 C9 . . . . 15.3(4) ? C7 C8 C9 C10 . . . . -179.8(3) ? C8 C9 C10 O1 . . . . -178.7(3) ? _cod_database_fobs_code 2244017