#------------------------------------------------------------------------------ #$Date: 2019-11-11 20:25:40 +0200 (Mon, 11 Nov 2019) $ #$Revision: 227260 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/03/58/4035843.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4035843 loop_ _publ_author_name 'Skalenko, Yevhen A.' 'Druzhenko, Tetiana V.' 'Denisenko, Aleksandr V.' 'Samoilenko, Maryna V.' 'Dacenko, Oleksandr P.' 'Trofymchuk, Serhii A.' 'Grygorenko, Oleksandr O.' 'Tolmachev, Andrey A.' 'Mykhailiuk, Pavel K.' _publ_section_title ; [2+2]-Photocycloaddition of N-Benzylmaleimide to Alkenes As an Approach to Functional 3-Azabicyclo[3.2.0]heptanes. ; _journal_issue 12 _journal_name_full 'The Journal of organic chemistry' _journal_page_first 6275 _journal_page_last 6289 _journal_paper_doi 10.1021/acs.joc.8b00077 _journal_volume 83 _journal_year 2018 _chemical_formula_sum 'C18 H19 N O4' _chemical_formula_weight 313.34 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _cell_angle_alpha 90 _cell_angle_beta 103.26(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 17.576(5) _cell_length_b 6.016(3) _cell_length_c 15.422(5) _cell_measurement_reflns_used 329 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 16.5 _cell_measurement_theta_min 3.5 _cell_volume 1587.2(11) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.1827 _diffrn_measured_fraction_theta_full 0.970 _diffrn_measured_fraction_theta_max 0.970 _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.279 _diffrn_reflns_av_unetI/netI 0.2796 _diffrn_reflns_Laue_measured_fraction_full 0.970 _diffrn_reflns_Laue_measured_fraction_max 0.970 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2609 _diffrn_reflns_point_group_measured_fraction_full 0.970 _diffrn_reflns_point_group_measured_fraction_max 0.970 _diffrn_reflns_theta_full 24.995 _diffrn_reflns_theta_max 24.995 _diffrn_reflns_theta_min 3.204 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.311 _exptl_crystal_description plate _exptl_crystal_F_000 664 _exptl_crystal_size_max 0.150 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.020 _refine_diff_density_max 0.185 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.055 _refine_ls_extinction_coef 0.016(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 0.792 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 210 _refine_ls_number_reflns 2609 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.792 _refine_ls_R_factor_all 0.3019 _refine_ls_R_factor_gt 0.0972 _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^)+(0.0589P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1902 _refine_ls_wR_factor_ref 0.2669 _reflns_Friedel_coverage 0.000 _reflns_number_gt 663 _reflns_number_total 2609 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file jo8b00077_si_002.cif _cod_data_source_block 23a_1 _cod_original_cell_volume 1587.1(10) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 4035843 _shelx_shelxl_version_number 2014/7 _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 0.986 _shelx_estimated_absorpt_t_max 0.998 _shelx_hkl_file ; -3 0 0 740829 23445 -2 3 0 0 740829 23445 1 -4 0 0 40712 8324 -2 4 0 0 40712 8324 1 -5 0 0 1170372 32680 -2 5 0 0 1170372 32680 1 -6 0 0 155089 8512 -2 6 0 0 155089 8512 1 -7 0 0 7549 5039 -2 7 0 0 7549 5039 1 -8 0 0 3907 1855 -2 8 0 0 3907 1855 1 -9 0 0 31029 4579 -2 9 0 0 31029 4579 1 -10 0 0 5830 3991 -2 10 0 0 5830 3991 1 -11 0 0 3843 2343 -2 11 0 0 3843 2343 1 -12 0 0 2540 1484 -2 12 0 0 2540 1484 1 -13 0 0 388 873 -2 13 0 0 388 873 1 -14 0 0 1980 1124 -2 14 0 0 1980 1124 1 -15 0 0 0 1827 -2 15 0 0 0 1827 1 -16 0 0 0 3386 -2 16 0 0 0 3386 1 17 0 0 12872 5292 1 18 0 0 2022 3513 1 19 0 0 767 2016 1 20 0 0 1072 3056 1 -1 -1 0 2371968 63402 -2 1 1 0 2371968 63402 1 -2 -1 0 22114 1686 -2 2 1 0 22114 1686 1 -3 -1 0 0 415 -2 3 1 0 0 415 1 -4 -1 0 879474 35489 -2 4 1 0 879474 35489 1 -5 -1 0 239157 18938 -2 5 1 0 239157 18938 1 -6 -1 0 20928 3664 -2 6 1 0 20928 3664 1 -7 -1 0 12986 3723 -2 7 1 0 12986 3723 1 -8 -1 0 490 451 -2 8 1 0 490 451 1 -9 -1 0 149194 16957 -2 9 1 0 149194 16957 1 -10 -1 0 22954 8483 -2 10 1 0 22954 8483 1 -11 -1 0 1639 1404 -2 11 1 0 1639 1404 1 -12 -1 0 18483 5079 -2 12 1 0 18483 5079 1 -13 -1 0 330 1069 -2 13 1 0 330 1069 1 -14 -1 0 18 1182 -2 14 1 0 18 1182 1 -15 -1 0 7915 2354 -2 15 1 0 7915 2354 1 -16 -1 0 4928 2099 -2 16 1 0 4928 2099 1 17 1 0 3087 2199 1 18 1 0 3291 1795 1 19 1 0 1242 2065 1 20 1 0 1950 2676 1 0 -2 0 24379 4299 -2 0 2 0 24379 4299 1 -1 -2 0 0 450 -2 1 2 0 0 450 1 -2 -2 0 299181 13666 -2 2 2 0 299181 13666 1 -3 -2 0 7059 1476 -2 3 2 0 7059 1476 1 -4 -2 0 0 1025 -2 4 2 0 0 1025 1 -5 -2 0 0 893 -2 5 2 0 0 893 1 -6 -2 0 6981 1373 -2 6 2 0 6981 1373 1 -7 -2 0 1455 791 -2 7 2 0 1455 791 1 -8 -2 0 197144 11967 -2 8 2 0 197144 11967 1 -9 -2 0 7075 2156 -2 9 2 0 7075 2156 1 -10 -2 0 32900 4326 -2 10 2 0 32900 4326 1 -11 -2 0 630 1215 -2 11 2 0 630 1215 1 -12 -2 0 1185 6726 -2 12 2 0 1185 6726 1 -13 -2 0 19251 8300 -2 13 2 0 19251 8300 1 -14 -2 0 2137 1068 -2 14 2 0 2137 1068 1 -15 -2 0 0 1465 -2 15 2 0 0 1465 1 -16 -2 0 2468 1774 -2 16 2 0 2468 1774 1 17 2 0 4272 2301 1 18 2 0 3993 2675 1 19 2 0 3878 1968 1 -1 -3 0 98617 8126 -2 1 3 0 98617 8126 1 -2 -3 0 273871 15901 -2 2 3 0 273871 15901 1 -3 -3 0 216776 12410 -2 3 3 0 216776 12410 1 -4 -3 0 7320 1746 -2 4 3 0 7320 1746 1 -5 -3 0 19439 3076 -2 5 3 0 19439 3076 1 -6 -3 0 4992 2821 -2 6 3 0 4992 2821 1 -7 -3 0 3612 1317 -2 7 3 0 3612 1317 1 -8 -3 0 6331 3419 -2 8 3 0 6331 3419 1 -9 -3 0 8995 3307 -2 9 3 0 8995 3307 1 -10 -3 0 1234 2022 -2 10 3 0 1234 2022 1 -11 -3 0 0 3179 -2 11 3 0 0 3179 1 -12 -3 0 8317 3831 -2 12 3 0 8317 3831 1 -13 -3 0 403 2710 -2 13 3 0 403 2710 1 -14 -3 0 2433 2669 -2 14 3 0 2433 2669 1 -15 -3 0 3333 3476 -2 15 3 0 3333 3476 1 -16 -3 0 0 2615 -2 16 3 0 0 2615 1 17 3 0 1945 2634 1 18 3 0 852 2957 1 0 -4 0 67283 10892 -2 0 4 0 67283 10892 1 -1 -4 0 700 1818 -2 1 4 0 700 1818 1 -2 -4 0 45627 5969 -2 2 4 0 45627 5969 1 -3 -4 0 5597 2908 -2 3 4 0 5597 2908 1 -4 -4 0 7143 2233 -2 4 4 0 7143 2233 1 -5 -4 0 9030 2291 -2 5 4 0 9030 2291 1 -6 -4 0 13057 2596 -2 6 4 0 13057 2596 1 -7 -4 0 2476 1373 -2 7 4 0 2476 1373 1 -8 -4 0 5719 1415 -2 8 4 0 5719 1415 1 -9 -4 0 0 1027 -2 9 4 0 0 1027 1 -10 -4 0 0 2201 -2 10 4 0 0 2201 1 -11 -4 0 343 1950 -2 11 4 0 343 1950 1 -12 -4 0 82 2155 -2 12 4 0 82 2155 1 -13 -4 0 0 4813 -2 13 4 0 0 4813 1 -14 -4 0 1243 1689 -2 14 4 0 1243 1689 1 -15 -4 0 0 3191 -2 15 4 0 0 3191 1 -16 -4 0 93 3331 -2 16 4 0 93 3331 1 -1 -5 0 821 2644 -2 1 5 0 821 2644 1 -2 -5 0 2071 1357 -2 2 5 0 2071 1357 1 -3 -5 0 1088 2419 -2 3 5 0 1088 2419 1 -4 -5 0 3285 2150 -2 4 5 0 3285 2150 1 -5 -5 0 320 2284 -2 5 5 0 320 2284 1 -6 -5 0 3530 2245 -2 6 5 0 3530 2245 1 -7 -5 0 5438 2275 -2 7 5 0 5438 2275 1 -8 -5 0 3381 1399 -2 8 5 0 3381 1399 1 -9 -5 0 15774 3863 -2 9 5 0 15774 3863 1 -10 -5 0 5698 3141 -2 10 5 0 5698 3141 1 -11 -5 0 6385 4158 -2 11 5 0 6385 4158 1 -12 -5 0 2221 2538 -2 12 5 0 2221 2538 1 -13 -5 0 8169 5064 -2 13 5 0 8169 5064 1 -14 -5 0 691 3734 -2 14 5 0 691 3734 1 0 -6 0 1253 1734 -2 0 6 0 1253 1734 1 -1 -6 0 8818 3215 -2 1 6 0 8818 3215 1 -2 -6 0 18705 5883 -2 2 6 0 18705 5883 1 -3 -6 0 0 2951 -2 3 6 0 0 2951 1 -4 -6 0 0 2829 -2 4 6 0 0 2829 1 -5 -6 0 4331 2561 -2 5 6 0 4331 2561 1 -6 -6 0 0 899 -2 6 6 0 0 899 1 -7 -6 0 8088 3190 -2 7 6 0 8088 3190 1 -8 -6 0 2598 2998 -2 8 6 0 2598 2998 1 -9 -6 0 0 6082 -2 9 6 0 0 6082 1 -10 -6 0 674 2151 -2 10 6 0 674 2151 1 -11 -6 0 2056 3441 -2 11 6 0 2056 3441 1 -1 -7 0 0 2106 -2 1 7 0 0 2106 1 -2 -7 0 1297 3521 -2 2 7 0 1297 3521 1 -3 -7 0 3166 3017 -2 3 7 0 3166 3017 1 -4 -7 0 3101 3677 -2 4 7 0 3101 3677 1 -20 1 1 0 1707 1 -19 1 1 166 1835 1 -18 1 1 1039 1602 1 -17 1 1 515 1085 1 -16 1 1 1556 1164 1 -15 1 1 15424 6645 1 -14 1 1 5119 2065 1 -13 1 1 10646 2013 1 -12 1 1 0 797 1 -11 1 1 48062 12972 1 -10 1 1 54897 9991 1 -9 1 1 3627 1498 1 -8 1 1 15336 6218 1 -7 1 1 110142 9673 1 -6 1 1 4298 1543 1 -5 1 1 23086 2863 1 -4 1 1 0 1001 1 -3 1 1 65244 4748 1 -2 1 1 123034 4890 1 -1 1 1 9486 1193 1 0 1 1 4178 689 1 1 1 1 61146 2831 1 2 1 1 304827 11415 1 3 1 1 778557 27991 1 4 1 1 264731 21243 1 5 1 1 139172 18003 1 6 1 1 401948 83100 1 7 1 1 5888 3769 1 8 1 1 6747 2582 1 9 1 1 3492 1667 1 10 1 1 1586 804 1 11 1 1 4498 1506 1 12 1 1 931 1028 1 13 1 1 687 911 1 14 1 1 1168 1230 1 15 1 1 0 671 1 16 1 1 5243 3913 1 17 1 1 230 1193 1 18 1 1 0 2024 1 19 1 1 0 1823 1 -19 2 1 1645 1848 1 -18 2 1 236 1142 1 -17 2 1 557 1177 1 -16 2 1 5241 2696 1 -15 2 1 0 1612 1 -14 2 1 5552 2095 1 -13 2 1 1173 2798 1 -12 2 1 7658 3403 1 -11 2 1 5715 2169 1 -10 2 1 21933 3226 1 -9 2 1 11164 2660 1 -8 2 1 8222 1980 1 -7 2 1 3309 1006 1 -6 2 1 23950 3795 1 -5 2 1 13675 3830 1 -4 2 1 10508 1645 1 -3 2 1 5016 1859 1 -2 2 1 2514 538 1 -1 2 1 12650 1845 1 0 2 1 91720 8125 1 1 2 1 34089 3712 1 2 2 1 4975 1461 1 3 2 1 0 1096 1 4 2 1 3406 1068 1 5 2 1 44595 4241 1 6 2 1 32094 3381 1 7 2 1 0 719 1 8 2 1 75056 9405 1 9 2 1 15972 4822 1 10 2 1 1471 2240 1 11 2 1 26046 6660 1 12 2 1 1438 2667 1 13 2 1 1386 1490 1 14 2 1 14965 7621 1 15 2 1 246 2253 1 16 2 1 0 1433 1 17 2 1 706 1546 1 18 2 1 0 2638 1 19 2 1 537 1799 1 -18 3 1 0 3049 1 -17 3 1 0 4095 1 -16 3 1 2124 2413 1 -15 3 1 0 1877 1 -14 3 1 0 3558 1 -13 3 1 7516 3750 1 -12 3 1 2473 2696 1 -11 3 1 42449 8192 1 -10 3 1 11284 3887 1 -9 3 1 0 1493 1 -8 3 1 2453 1351 1 -7 3 1 10699 2312 1 -6 3 1 0 1268 1 -5 3 1 3166 962 1 -4 3 1 34828 4128 1 -3 3 1 46682 4620 1 -2 3 1 26429 3936 1 -1 3 1 4272 1432 1 0 3 1 0 1031 1 1 3 1 14755 2607 1 2 3 1 57510 5859 1 3 3 1 42831 4569 1 4 3 1 1261 841 1 5 3 1 0 818 1 6 3 1 3177 1741 1 7 3 1 940 1173 1 8 3 1 1055 2685 1 9 3 1 4074 2621 1 10 3 1 0 2788 1 11 3 1 9102 3871 1 12 3 1 1014 1854 1 13 3 1 0 3756 1 14 3 1 1930 3468 1 15 3 1 1003 2596 1 16 3 1 3512 2861 1 17 3 1 1026 2081 1 18 3 1 0 3046 1 -17 4 1 0 5610 1 -16 4 1 134 1967 1 -15 4 1 2025 2345 1 -14 4 1 866 3799 1 -13 4 1 0 1981 1 -12 4 1 1226 1493 1 -11 4 1 508 1253 1 -10 4 1 158 1287 1 -9 4 1 1985 1131 1 -8 4 1 3671 1918 1 -7 4 1 0 1226 1 -6 4 1 22299 3842 1 -5 4 1 2124 1770 1 -4 4 1 25014 4359 1 -3 4 1 2740 1791 1 -2 4 1 11375 3269 1 -1 4 1 1629 2407 1 0 4 1 2703 2156 1 1 4 1 14273 2919 1 2 4 1 0 905 1 3 4 1 6137 1670 1 4 4 1 21763 3806 1 5 4 1 0 875 1 6 4 1 4946 1759 1 7 4 1 15604 4869 1 8 4 1 464 1228 1 9 4 1 16168 4609 1 10 4 1 11264 3947 1 11 4 1 0 1554 1 12 4 1 2297 1872 1 13 4 1 0 3482 1 14 4 1 0 4474 1 15 4 1 950 2521 1 16 4 1 0 4638 1 -14 5 1 0 2880 1 -13 5 1 7137 4752 1 -12 5 1 4433 4499 1 -11 5 1 0 2008 1 -10 5 1 69 3263 1 -9 5 1 979 2572 1 -8 5 1 1648 1661 1 -7 5 1 574 1816 1 -6 5 1 0 1308 1 -5 5 1 250 2620 1 -4 5 1 876 2227 1 -3 5 1 1917 2465 1 -2 5 1 849 991 1 -1 5 1 446 1728 1 0 5 1 2246 1902 1 1 5 1 2763 1818 1 2 5 1 0 2560 1 3 5 1 5894 2182 1 4 5 1 21820 4475 1 5 5 1 9079 2825 1 6 5 1 0 1569 1 7 5 1 0 944 1 8 5 1 1018 1476 1 9 5 1 0 1142 1 10 5 1 0 2392 1 11 5 1 1794 2125 1 12 5 1 191 2136 1 13 5 1 1948 5715 1 14 5 1 0 4186 1 -11 6 1 2944 3659 1 -10 6 1 1491 1986 1 -9 6 1 1824 2691 1 -8 6 1 0 4048 1 -7 6 1 2083 2014 1 -6 6 1 0 3789 1 -5 6 1 1377 2517 1 -4 6 1 2085 1660 1 -3 6 1 4062 3946 1 -2 6 1 3330 1970 1 -1 6 1 897 2121 1 0 6 1 2006 3170 1 1 6 1 5460 2338 1 2 6 1 1559 2859 1 3 6 1 4313 1910 1 4 6 1 677 2041 1 5 6 1 2887 2152 1 6 6 1 0 1523 1 7 6 1 1012 1663 1 8 6 1 1489 4017 1 9 6 1 1595 4264 1 10 6 1 506 4505 1 -4 7 1 2988 2496 1 -3 7 1 4236 3072 1 -2 7 1 479 4094 1 -1 7 1 0 4087 1 0 7 1 0 3724 1 1 7 1 1929 3336 1 2 7 1 510 3824 1 3 7 1 1402 2684 1 -20 0 2 1018 2312 1 -19 0 2 3247 3104 1 -18 0 2 1633 1281 1 -17 0 2 3615 2742 1 15 0 2 17606 4444 -2 -16 0 2 17606 4444 1 14 0 2 0 1096 -2 -15 0 2 0 1096 1 13 0 2 84733 9711 -2 -14 0 2 84733 9711 1 12 0 2 37021 6331 -2 -13 0 2 37021 6331 1 11 0 2 1894 1419 -2 -12 0 2 1894 1419 1 10 0 2 100213 10168 -2 -11 0 2 100213 10168 1 9 0 2 58970 7165 -2 -10 0 2 58970 7165 1 8 0 2 163887 10536 -2 -9 0 2 163887 10536 1 7 0 2 3828 3414 -2 -8 0 2 3828 3414 1 6 0 2 349401 15757 -2 -7 0 2 349401 15757 1 5 0 2 1169 1399 -2 -6 0 2 1169 1399 1 4 0 2 140877 12219 -2 -5 0 2 140877 12219 1 3 0 2 2258568 87095 -2 -4 0 2 2258568 87095 1 2 0 2 155656 18662 -2 -3 0 2 155656 18662 1 1 0 2 755867 58685 -2 -2 0 2 755867 58685 1 -2 0 2 1415622 72354 -2 1 0 2 1415622 72354 1 -3 0 2 88087 15036 -2 2 0 2 88087 15036 1 -4 0 2 1799904 60799 -2 3 0 2 1799904 60799 1 -5 0 2 144182 16081 -2 4 0 2 144182 16081 1 -6 0 2 4599 1168 -2 5 0 2 4599 1168 1 -7 0 2 359275 15965 -2 6 0 2 359275 15965 1 -8 0 2 9337 1588 -2 7 0 2 9337 1588 1 -9 0 2 130131 8516 -2 8 0 2 130131 8516 1 -10 0 2 33353 7812 -2 9 0 2 33353 7812 1 -11 0 2 66451 21126 -2 10 0 2 66451 21126 1 -12 0 2 261 1323 -2 11 0 2 261 1323 1 -13 0 2 26656 11069 -2 12 0 2 26656 11069 1 -14 0 2 43404 17374 -2 13 0 2 43404 17374 1 -15 0 2 0 1537 -2 14 0 2 0 1537 1 -16 0 2 8946 8557 -2 15 0 2 8946 8557 1 16 0 2 1999 3056 1 17 0 2 513 1353 1 18 0 2 1669 2766 1 19 0 2 0 4465 1 -20 1 2 1122 2725 1 -19 1 2 1600 1866 1 -18 1 2 4722 2290 1 -17 1 2 0 713 1 15 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1 -12 1 12 464 1142 1 -11 1 12 0 2549 1 -10 1 12 5901 2808 1 -9 1 12 6605 2706 1 -8 1 12 3079 2455 1 1 -1 12 0 874 -2 -7 1 12 0 874 1 0 -1 12 2773 1331 -2 -6 1 12 2773 1331 1 -1 -1 12 13921 7272 -2 -5 1 12 13921 7272 1 -2 -1 12 7165 3108 -2 -4 1 12 7165 3108 1 -3 -1 12 7744 2936 -2 -3 1 12 7744 2936 1 -4 -1 12 4435 2271 -2 -2 1 12 4435 2271 1 -5 -1 12 2821 1307 -2 -1 1 12 2821 1307 1 -6 -1 12 893 1143 -2 0 1 12 893 1143 1 -7 -1 12 3815 2255 -2 1 1 12 3815 2255 1 2 1 12 758 3597 1 3 1 12 3120 3198 1 4 1 12 3535 3647 1 5 1 12 0 3950 1 6 1 12 0 2649 1 7 1 12 5544 4870 1 8 1 12 7238 3081 1 9 1 12 122 2329 1 10 1 12 7774 5116 1 11 1 12 2217 5398 1 -17 2 12 2533 2300 1 -16 2 12 15 1852 1 -15 2 12 0 2300 1 -14 2 12 0 3414 1 -13 2 12 0 1986 1 -12 2 12 0 3994 1 -11 2 12 0 3024 1 -10 2 12 14181 3903 1 -9 2 12 313 839 1 -8 2 12 676 1539 1 1 -2 12 5469 4497 -2 -7 2 12 5469 4497 1 0 -2 12 2565 2372 -2 -6 2 12 2565 2372 1 -1 -2 12 1605 1939 -2 -5 2 12 1605 1939 1 -2 -2 12 1233 1124 -2 -4 2 12 1233 1124 1 -3 -2 12 0 1375 -2 -3 2 12 0 1375 1 -4 -2 12 1259 1095 -2 -2 2 12 1259 1095 1 -5 -2 12 0 1702 -2 -1 2 12 0 1702 1 -6 -2 12 3247 2022 -2 0 2 12 3247 2022 1 -7 -2 12 3077 3336 -2 1 2 12 3077 3336 1 2 2 12 1031 3244 1 3 2 12 2699 1647 1 4 2 12 0 2146 1 5 2 12 0 2424 1 6 2 12 0 2249 1 7 2 12 92 4410 1 8 2 12 228 1918 1 9 2 12 8678 4962 1 10 2 12 1339 4508 1 11 2 12 1089 2983 1 -15 3 12 0 2667 1 -14 3 12 0 3824 1 -13 3 12 4747 4260 1 -12 3 12 1707 2948 1 -11 3 12 0 1578 1 -10 3 12 2120 3046 1 -9 3 12 5056 3852 1 -8 3 12 0 2852 1 1 -3 12 6739 4959 -2 -7 3 12 6739 4959 1 0 -3 12 3310 2122 -2 -6 3 12 3310 2122 1 -1 -3 12 0 3268 -2 -5 3 12 0 3268 1 -2 -3 12 383 3509 -2 -4 3 12 383 3509 1 -3 -3 12 579 3870 -2 -3 3 12 579 3870 1 -4 -3 12 5502 4798 -2 -2 3 12 5502 4798 1 -5 -3 12 4583 2297 -2 -1 3 12 4583 2297 1 -6 -3 12 4046 5404 -2 0 3 12 4046 5404 1 -7 -3 12 0 3178 -2 1 3 12 0 3178 1 2 3 12 1780 5033 1 3 3 12 296 2844 1 4 3 12 96 1920 1 5 3 12 0 4897 1 6 3 12 0 3546 1 7 3 12 3482 3763 1 8 3 12 6387 6118 1 9 3 12 0 3422 1 -13 4 12 4921 5418 1 -12 4 12 0 7331 1 -11 4 12 0 4077 1 -10 4 12 849 1881 1 -9 4 12 0 1373 1 2 -4 12 0 4317 -2 -8 4 12 0 4317 1 1 -4 12 1242 3236 -2 -7 4 12 1242 3236 1 0 -4 12 0 1797 -2 -6 4 12 0 1797 1 -1 -4 12 941 2959 -2 -5 4 12 941 2959 1 -2 -4 12 0 2721 -2 -4 4 12 0 2721 1 -3 -4 12 4184 1856 -2 -3 4 12 4184 1856 1 -4 -4 12 2845 4302 -2 -2 4 12 2845 4302 1 -5 -4 12 2533 2049 -2 -1 4 12 2533 2049 1 -6 -4 12 4366 2661 -2 0 4 12 4366 2661 1 -7 -4 12 0 3816 -2 1 4 12 0 3816 1 -8 -4 12 0 4096 -2 2 4 12 0 4096 1 3 4 12 662 1515 1 4 4 12 0 4848 1 5 4 12 3035 3413 1 6 4 12 0 5556 1 7 4 12 0 3105 1 -9 5 12 0 2861 1 2 -5 12 1759 3300 -2 -8 5 12 1759 3300 1 1 -5 12 0 1492 -2 -7 5 12 0 1492 1 0 -5 12 1458 2771 -2 -6 5 12 1458 2771 1 -1 -5 12 5892 3623 -2 -5 5 12 5892 3623 1 -2 -5 12 2394 3353 -2 -4 5 12 2394 3353 1 -3 -5 12 0 2007 -2 -3 5 12 0 2007 1 -4 -5 12 0 1081 -2 -2 5 12 0 1081 1 -5 -5 12 0 2447 -2 -1 5 12 0 2447 1 -6 -5 12 1343 3635 -2 0 5 12 1343 3635 1 -7 -5 12 2916 5416 -2 1 5 12 2916 5416 1 -8 -5 12 2254 4715 -2 2 5 12 2254 4715 1 -17 1 13 1117 2164 1 -16 1 13 0 3025 1 -15 1 13 1538 2376 1 -14 1 13 599 1366 1 -13 1 13 0 3134 1 -12 1 13 1581 2440 1 -11 1 13 512 2047 1 -10 1 13 2401 1753 1 -9 1 13 551 1178 1 -8 1 13 3227 1587 1 -7 1 13 20951 14594 1 -6 1 13 2048 1804 1 -5 1 13 2651 1894 1 -4 1 13 2462 4423 1 -3 1 13 6904 2697 1 -2 1 13 629 2172 1 -1 1 13 1425 1332 1 0 1 13 5587 5513 1 1 1 13 267 2010 1 2 1 13 198 1577 1 3 1 13 872 2492 1 4 1 13 680 3703 1 5 1 13 3752 2714 1 6 1 13 824 2947 1 7 1 13 2252 3102 1 8 1 13 0 5008 1 9 1 13 1124 2213 1 10 1 13 0 2616 1 -16 2 13 0 2409 1 -15 2 13 0 4101 1 -14 2 13 1070 3805 1 -13 2 13 2924 3014 1 -12 2 13 4780 6146 1 -11 2 13 0 5519 1 -10 2 13 12226 8293 1 -9 2 13 1742 1325 1 -8 2 13 2073 3119 1 -7 2 13 1488 1973 1 -6 2 13 6745 4409 1 -5 2 13 18551 4252 1 -4 2 13 7980 6047 1 -3 2 13 6479 4277 1 -2 2 13 10139 3957 1 -1 2 13 1584 1149 1 0 2 13 3239 2703 1 1 2 13 1764 1083 1 2 2 13 218 3215 1 3 2 13 2776 1740 1 4 2 13 0 2610 1 5 2 13 4190 2641 1 6 2 13 0 5471 1 7 2 13 784 1838 1 8 2 13 5789 6522 1 9 2 13 7939 5524 1 -14 3 13 0 7029 1 -13 3 13 0 5362 1 -12 3 13 2132 2755 1 -11 3 13 1227 1839 1 -10 3 13 7896 6260 1 -9 3 13 2725 2189 1 -8 3 13 6510 3182 1 -7 3 13 2093 2574 1 -6 3 13 0 2203 1 -5 3 13 2828 2302 1 -4 3 13 18539 5857 1 -3 3 13 28361 8916 1 -2 3 13 6830 3844 1 -1 3 13 4058 2151 1 0 3 13 2824 1715 1 1 3 13 3522 3155 1 2 3 13 1050 3419 1 3 3 13 3727 3583 1 4 3 13 10763 8645 1 5 3 13 0 2146 1 6 3 13 1529 4854 1 7 3 13 2789 7182 1 8 3 13 0 3845 1 -12 4 13 0 915 1 -11 4 13 0 3663 1 -10 4 13 831 4609 1 -9 4 13 2826 3270 1 -8 4 13 3685 4034 1 -7 4 13 0 4038 1 -6 4 13 3850 3068 1 -5 4 13 0 4041 1 -4 4 13 0 3664 1 -3 4 13 1029 4726 1 -2 4 13 0 2289 1 -1 4 13 0 5164 1 0 4 13 2112 4746 1 1 4 13 1607 1498 1 2 4 13 4570 4442 1 3 4 13 0 2217 1 4 4 13 0 6082 1 5 4 13 4855 19339 1 -5 5 13 2051 5415 1 -4 5 13 0 5290 1 -3 5 13 2211 7741 1 -2 5 13 0 3335 1 -16 0 14 164 3383 1 -15 0 14 3124 3265 1 -14 0 14 0 3866 1 -13 0 14 1625 1718 1 -12 0 14 2001 1979 1 -11 0 14 0 3726 1 -10 0 14 0 1723 1 -9 0 14 2691 2058 1 -8 0 14 0 1872 1 0 0 14 5783 9556 -2 -7 0 14 5783 9556 1 -1 0 14 855 2245 -2 -6 0 14 855 2245 1 -2 0 14 0 3826 -2 -5 0 14 0 3826 1 -3 0 14 8511 5000 -2 -4 0 14 8511 5000 1 -4 0 14 112 3811 -2 -3 0 14 112 3811 1 -5 0 14 0 1313 -2 -2 0 14 0 1313 1 -6 0 14 3881 2934 -2 -1 0 14 3881 2934 1 -7 0 14 1651 2302 -2 0 0 14 1651 2302 1 1 0 14 195 10474 1 2 0 14 5137 3922 1 3 0 14 7754 3732 1 4 0 14 3529 4891 1 5 0 14 6403 7691 1 6 0 14 0 11658 1 7 0 14 18462 14725 1 8 0 14 2363 1732 1 9 0 14 0 16161 1 -16 1 14 1642 2437 1 -15 1 14 42 1694 1 -14 1 14 594 1459 1 -13 1 14 0 2227 1 -12 1 14 0 890 1 -11 1 14 0 2969 1 -10 1 14 565 2312 1 -9 1 14 1003 2286 1 -8 1 14 4005 2489 1 0 -1 14 1587 1100 -2 -7 1 14 1587 1100 1 -1 -1 14 7161 5048 -2 -6 1 14 7161 5048 1 -2 -1 14 1628 2493 -2 -5 1 14 1628 2493 1 -3 -1 14 145 1535 -2 -4 1 14 145 1535 1 -4 -1 14 1381 1757 -2 -3 1 14 1381 1757 1 -5 -1 14 1220 2471 -2 -2 1 14 1220 2471 1 -6 -1 14 268 1255 -2 -1 1 14 268 1255 1 -7 -1 14 0 1633 -2 0 1 14 0 1633 1 1 1 14 701 1015 1 2 1 14 4290 1926 1 3 1 14 648 1049 1 4 1 14 0 2535 1 5 1 14 1792 2572 1 6 1 14 1107 5381 1 7 1 14 0 4433 1 8 1 14 0 6318 1 9 1 14 0 3291 1 -15 2 14 976 2950 1 -14 2 14 0 3963 1 -13 2 14 0 4650 1 -12 2 14 0 12691 1 -11 2 14 3527 5516 1 -10 2 14 0 4033 1 -9 2 14 4160 4455 1 -8 2 14 0 1436 1 0 -2 14 7341 10079 -2 -7 2 14 7341 10079 1 -1 -2 14 0 2239 -2 -6 2 14 0 2239 1 -2 -2 14 0 2701 -2 -5 2 14 0 2701 1 -3 -2 14 1183 3287 -2 -4 2 14 1183 3287 1 -4 -2 14 4014 2554 -2 -3 2 14 4014 2554 1 -5 -2 14 5914 2630 -2 -2 2 14 5914 2630 1 -6 -2 14 5360 4780 -2 -1 2 14 5360 4780 1 -7 -2 14 0 1765 -2 0 2 14 0 1765 1 1 2 14 633 1864 1 2 2 14 220 2941 1 3 2 14 2211 2200 1 4 2 14 2440 3068 1 5 2 14 0 5002 1 6 2 14 0 3099 1 7 2 14 5432 4490 1 8 2 14 0 2796 1 -13 3 14 0 3800 1 -12 3 14 3444 3119 1 -11 3 14 0 3719 1 -10 3 14 0 3565 1 -9 3 14 186 702 1 -8 3 14 0 3593 1 0 -3 14 1618 1824 -2 -7 3 14 1618 1824 1 -1 -3 14 687 3621 -2 -6 3 14 687 3621 1 -2 -3 14 0 3803 -2 -5 3 14 0 3803 1 -3 -3 14 420 3036 -2 -4 3 14 420 3036 1 -4 -3 14 384 4435 -2 -3 3 14 384 4435 1 -5 -3 14 0 4223 -2 -2 3 14 0 4223 1 -6 -3 14 11331 4796 -2 -1 3 14 11331 4796 1 -7 -3 14 2281 1553 -2 0 3 14 2281 1553 1 1 3 14 719 2588 1 2 3 14 3423 3495 1 3 3 14 3779 2154 1 4 3 14 2058 5468 1 5 3 14 0 4397 1 6 3 14 4066 2843 1 -10 4 14 407 3827 1 -9 4 14 0 3621 1 1 -4 14 0 3344 -2 -8 4 14 0 3344 1 0 -4 14 0 3389 -2 -7 4 14 0 3389 1 -1 -4 14 0 2228 -2 -6 4 14 0 2228 1 -2 -4 14 709 5645 -2 -5 4 14 709 5645 1 -3 -4 14 417 4456 -2 -4 4 14 417 4456 1 -4 -4 14 0 4077 -2 -3 4 14 0 4077 1 -5 -4 14 0 4954 -2 -2 4 14 0 4954 1 -6 -4 14 2488 2812 -2 -1 4 14 2488 2812 1 -7 -4 14 0 4531 -2 0 4 14 0 4531 1 -8 -4 14 0 5817 -2 1 4 14 0 5817 1 2 4 14 0 1048 1 -15 1 15 1820 3016 1 -14 1 15 587 2007 1 -13 1 15 1844 2007 1 -12 1 15 0 1031 1 -11 1 15 357 5821 1 -10 1 15 2235 3749 1 -9 1 15 2657 4045 1 -8 1 15 1088 1380 1 -7 1 15 0 1303 1 -6 1 15 3266 2186 1 -5 1 15 2503 1261 1 -4 1 15 3235 1522 1 -3 1 15 280 2379 1 -2 1 15 962 3412 1 -1 1 15 2261 1417 1 0 1 15 4874 2693 1 1 1 15 835 2942 1 2 1 15 0 2378 1 3 1 15 203 1553 1 4 1 15 0 1521 1 5 1 15 1216 3024 1 6 1 15 163 3591 1 7 1 15 0 1900 1 -14 2 15 3181 7238 1 -13 2 15 0 3312 1 -12 2 15 1466 5134 1 -11 2 15 0 3786 1 -10 2 15 0 4627 1 -9 2 15 4458 2473 1 -8 2 15 4519 4650 1 -7 2 15 0 3041 1 -6 2 15 0 2314 1 -5 2 15 1074 4762 1 -4 2 15 0 3367 1 -3 2 15 4256 3660 1 -2 2 15 8822 4942 1 -1 2 15 1016 1696 1 0 2 15 4307 2541 1 1 2 15 824 1904 1 2 2 15 857 1801 1 3 2 15 0 2754 1 4 2 15 4292 3818 1 5 2 15 3803 4602 1 6 2 15 821 4409 1 -11 3 15 0 3646 1 -10 3 15 2235 3844 1 -9 3 15 0 5451 1 -8 3 15 1565 2385 1 -7 3 15 4524 3125 1 -6 3 15 0 3269 1 -5 3 15 0 3209 1 -4 3 15 0 4549 1 -3 3 15 2633 2784 1 -2 3 15 490 2148 1 -1 3 15 770 4159 1 0 3 15 0 3361 1 1 3 15 5518 5147 1 2 3 15 1164 3096 1 3 3 15 0 2342 1 4 3 15 652 1897 1 -6 4 15 0 3143 1 -5 4 15 0 4373 1 -4 4 15 5073 6582 1 -3 4 15 0 3297 1 -2 4 15 0 3771 1 -14 0 16 0 5916 1 -13 0 16 8 7399 1 -12 0 16 755 7232 1 -11 0 16 3268 3065 1 -10 0 16 5532 4858 1 -9 0 16 0 4095 1 -8 0 16 3287 4264 1 -1 0 16 0 1405 -2 -7 0 16 0 1405 1 -2 0 16 0 1092 -2 -6 0 16 0 1092 1 -3 0 16 3207 3975 -2 -5 0 16 3207 3975 1 -4 0 16 4628 2502 -2 -4 0 16 4628 2502 1 -5 0 16 1526 3773 -2 -3 0 16 1526 3773 1 -6 0 16 0 3614 -2 -2 0 16 0 3614 1 -7 0 16 1121 2418 -2 -1 0 16 1121 2418 1 0 0 16 1037 4527 1 1 0 16 0 7374 1 2 0 16 0 3131 1 3 0 16 0 3421 1 4 0 16 0 2857 1 5 0 16 197 4157 1 -13 1 16 5243 4305 1 -12 1 16 664 1827 1 -11 1 16 177 4976 1 -10 1 16 0 3707 1 -9 1 16 0 5215 1 -8 1 16 1386 1903 1 -1 -1 16 0 1226 -2 -7 1 16 0 1226 1 -2 -1 16 157 2311 -2 -6 1 16 157 2311 1 -3 -1 16 2335 1675 -2 -5 1 16 2335 1675 1 -4 -1 16 1043 3061 -2 -4 1 16 1043 3061 1 -5 -1 16 18 1625 -2 -3 1 16 18 1625 1 -6 -1 16 1639 2964 -2 -2 1 16 1639 2964 1 -7 -1 16 1216 1209 -2 -1 1 16 1216 1209 1 0 1 16 0 1856 1 1 1 16 0 1594 1 2 1 16 2385 846 1 3 1 16 552 2481 1 4 1 16 353 1665 1 5 1 16 546 3474 1 -12 2 16 2469 3297 1 -11 2 16 0 5079 1 -10 2 16 1086 4272 1 -9 2 16 0 4871 1 0 -2 16 0 2826 -2 -8 2 16 0 2826 1 -1 -2 16 0 1575 -2 -7 2 16 0 1575 1 -2 -2 16 0 1935 -2 -6 2 16 0 1935 1 -3 -2 16 7542 2843 -2 -5 2 16 7542 2843 1 -4 -2 16 0 3707 -2 -4 2 16 0 3707 1 -5 -2 16 2209 983 -2 -3 2 16 2209 983 1 -6 -2 16 760 2598 -2 -2 2 16 760 2598 1 -7 -2 16 2830 4225 -2 -1 2 16 2830 4225 1 -8 -2 16 0 3984 -2 0 2 16 0 3984 1 1 2 16 3225 1780 1 2 2 16 0 1594 1 3 2 16 1681 1941 1 -9 3 16 249 3368 1 0 -3 16 4309 3490 -2 -8 3 16 4309 3490 1 -1 -3 16 1962 4310 -2 -7 3 16 1962 4310 1 -2 -3 16 938 2666 -2 -6 3 16 938 2666 1 -3 -3 16 2667 6645 -2 -5 3 16 2667 6645 1 -4 -3 16 0 2750 -2 -4 3 16 0 2750 1 -5 -3 16 0 2524 -2 -3 3 16 0 2524 1 -6 -3 16 5886 4445 -2 -2 3 16 5886 4445 1 -7 -3 16 1765 4956 -2 -1 3 16 1765 4956 1 -8 -3 16 0 4256 -2 0 3 16 0 4256 1 -11 1 17 0 2067 1 -10 1 17 3535 4282 1 -9 1 17 0 4606 1 -8 1 17 0 3125 1 -7 1 17 0 4138 1 -6 1 17 4164 3852 1 -5 1 17 0 1334 1 -4 1 17 388 987 1 -3 1 17 750 1493 1 -2 1 17 0 2733 1 -1 1 17 1407 3301 1 0 1 17 2019 2368 1 1 1 17 2432 1544 1 2 1 17 1062 3098 1 -9 2 17 2780 3546 1 -8 2 17 2824 4908 1 -7 2 17 2696 5418 1 -6 2 17 773 1876 1 -5 2 17 1200 3377 1 -4 2 17 4149 2930 1 -3 2 17 1920 4326 1 -2 2 17 0 2576 1 -1 2 17 610 1839 1 0 2 17 2423 1885 1 -1 0 18 296 5745 -2 -8 0 18 296 5745 1 -2 0 18 4619 7882 -2 -7 0 18 4619 7882 1 -3 0 18 1503 2298 -2 -6 0 18 1503 2298 1 -4 0 18 0 2882 -2 -5 0 18 0 2882 1 -5 0 18 0 2740 -2 -4 0 18 0 2740 1 -6 0 18 0 3019 -2 -3 0 18 0 3019 1 -7 0 18 2846 3888 -2 -2 0 18 2846 3888 1 -8 0 18 0 3456 -2 -1 0 18 0 3456 1 -2 -1 18 4949 3560 -2 -7 1 18 4949 3560 1 -3 -1 18 0 10358 -2 -6 1 18 0 10358 1 -4 -1 18 1221 1579 -2 -5 1 18 1221 1579 1 -5 -1 18 2203 2419 -2 -4 1 18 2203 2419 1 -6 -1 18 0 2835 -2 -3 1 18 0 2835 1 ; _shelx_hkl_checksum 90175 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp O1 O 0.2551(3) -0.0391(9) 0.2673(4) 0.0915(19) Uani 1 1 d . . O2 O 0.3516(4) 0.5809(10) 0.4253(4) 0.104(2) Uani 1 1 d . . O3 O 0.0336(4) 0.5091(9) 0.3918(4) 0.105(2) Uani 1 1 d . . O4 O -0.0158(4) 0.1726(10) 0.3719(5) 0.097(2) Uani 1 1 d . . N1 N 0.3180(4) 0.2635(9) 0.3394(5) 0.0671(18) Uani 1 1 d . . C1 C 0.0874(5) 0.2145(11) 0.4956(6) 0.073(3) Uani 1 1 d . . H1 H 0.0560 0.1806 0.5389 0.087 Uiso 1 1 calc R U C2 C 0.1269(4) 0.0046(11) 0.4794(6) 0.077(2) Uani 1 1 d . . H2A H 0.0941 -0.0794 0.4314 0.092 Uiso 1 1 calc R U H2B H 0.1382 -0.0868 0.5326 0.092 Uiso 1 1 calc R U C3 C 0.2032(4) 0.0769(11) 0.4541(5) 0.068(2) Uani 1 1 d . . H3 H 0.2446 -0.0355 0.4669 0.081 Uiso 1 1 calc R U C4 C 0.1945(5) 0.1923(12) 0.3623(5) 0.065(2) Uani 1 1 d . . H4 H 0.1414 0.1941 0.3247 0.078 Uiso 1 1 calc R U C5 C 0.2561(4) 0.1277(14) 0.3168(6) 0.069(2) Uani 1 1 d . . C6 C 0.3048(5) 0.4336(15) 0.3934(6) 0.079(2) Uani 1 1 d . . C7 C 0.2224(4) 0.4138(11) 0.4091(5) 0.064(2) Uani 1 1 d . . H7 H 0.1879 0.5426 0.3934 0.077 Uiso 1 1 calc R U C8 C 0.2264(4) 0.3029(11) 0.5027(6) 0.064(2) Uani 1 1 d . . H8 H 0.2778 0.3060 0.5442 0.077 Uiso 1 1 calc R U C9 C 0.1561(5) 0.3636(14) 0.5436(5) 0.076(2) Uani 1 1 d . . H9A H 0.1687 0.3349 0.6071 0.092 Uiso 1 1 calc R U H9B H 0.1428 0.5195 0.5338 0.092 Uiso 1 1 calc R U C10 C 0.0346(5) 0.3236(14) 0.4181(6) 0.067(2) Uani 1 1 d . . C11 C -0.0715(6) 0.2480(12) 0.2932(8) 0.103(4) Uani 1 1 d . . H11A H -0.1036 0.1253 0.2668 0.154 Uiso 1 1 calc R U H11B H -0.1039 0.3619 0.3094 0.154 Uiso 1 1 calc R U H11C H -0.0441 0.3066 0.2511 0.154 Uiso 1 1 calc R U C12 C 0.3947(4) 0.2315(11) 0.3165(6) 0.078(3) Uani 1 1 d . . H12A H 0.4066 0.0740 0.3172 0.093 Uiso 1 1 calc R U H12B H 0.4351 0.3037 0.3611 0.093 Uiso 1 1 calc R U C13 C 0.3951(5) 0.3264(13) 0.2254(6) 0.068(2) Uani 1 1 d . . C14 C 0.3660(5) 0.5290(13) 0.1982(6) 0.084(3) Uani 1 1 d . . H14 H 0.3408 0.6112 0.2343 0.101 Uiso 1 1 calc R U C15 C 0.3730(5) 0.6151(14) 0.1182(6) 0.080(3) Uani 1 1 d . . H15 H 0.3488 0.7492 0.0986 0.097 Uiso 1 1 calc R U C16 C 0.4160(5) 0.5046(15) 0.0658(7) 0.094(3) Uani 1 1 d . . H16 H 0.4241 0.5657 0.0133 0.112 Uiso 1 1 calc R U C17 C 0.4465(5) 0.2939(15) 0.0970(8) 0.086(3) Uani 1 1 d . . H17 H 0.4720 0.2086 0.0621 0.103 Uiso 1 1 calc R U C18 C 0.4390(4) 0.2140(12) 0.1777(6) 0.070(2) Uani 1 1 d . . H18 H 0.4639 0.0827 0.1999 0.084 Uiso 1 1 calc R U loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.094(4) 0.085(4) 0.098(5) -0.031(4) 0.027(4) 0.005(3) O2 0.123(5) 0.085(4) 0.115(6) -0.018(4) 0.049(4) -0.031(4) O3 0.140(6) 0.054(4) 0.130(6) 0.026(4) 0.049(5) -0.002(3) O4 0.097(5) 0.074(4) 0.119(6) 0.001(4) 0.021(4) -0.011(4) N1 0.064(4) 0.068(4) 0.070(5) -0.017(4) 0.018(4) 0.002(3) C1 0.081(6) 0.049(4) 0.100(7) -0.004(4) 0.047(6) 0.007(4) C2 0.075(5) 0.043(4) 0.115(7) 0.003(4) 0.027(5) 0.010(4) C3 0.067(5) 0.041(4) 0.093(7) 0.010(4) 0.016(5) 0.015(3) C4 0.061(5) 0.067(5) 0.072(6) 0.002(4) 0.024(4) 0.005(4) C5 0.062(5) 0.061(5) 0.077(6) 0.005(5) 0.004(4) 0.010(4) C6 0.099(7) 0.070(6) 0.063(6) 0.017(5) 0.007(5) -0.001(5) C7 0.077(5) 0.042(4) 0.080(6) -0.011(4) 0.032(5) 0.001(4) C8 0.065(5) 0.051(4) 0.078(6) -0.003(4) 0.022(5) -0.005(4) C9 0.098(6) 0.073(5) 0.065(6) 0.002(5) 0.032(5) 0.003(5) C10 0.058(5) 0.059(5) 0.090(7) 0.015(5) 0.030(5) 0.004(4) C11 0.088(7) 0.088(8) 0.130(11) -0.001(6) 0.019(7) 0.016(5) C12 0.051(4) 0.084(6) 0.106(8) 0.033(5) 0.035(5) 0.015(4) C13 0.073(5) 0.058(5) 0.076(6) 0.012(4) 0.019(5) 0.015(4) C14 0.119(7) 0.069(5) 0.061(6) 0.001(5) 0.015(5) -0.002(5) C15 0.086(6) 0.064(5) 0.085(7) 0.015(5) 0.006(5) -0.001(5) C16 0.069(5) 0.091(7) 0.133(9) -0.006(6) 0.049(6) -0.015(5) C17 0.063(6) 0.081(6) 0.121(9) -0.023(6) 0.035(6) 0.006(4) C18 0.053(5) 0.069(5) 0.093(7) 0.015(5) 0.024(5) 0.005(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C10 O4 C11 117.9(7) C5 N1 C6 111.8(7) C5 N1 C12 125.9(6) C6 N1 C12 122.1(7) C10 C1 C2 117.9(8) C10 C1 C9 113.7(7) C2 C1 C9 103.2(6) C1 C2 C3 105.6(5) C2 C3 C4 116.6(6) C2 C3 C8 105.7(6) C4 C3 C8 90.5(5) C5 C4 C7 105.2(6) C5 C4 C3 112.8(6) C7 C4 C3 90.3(6) O1 C5 N1 122.8(7) O1 C5 C4 126.2(8) N1 C5 C4 110.9(7) O2 C6 N1 126.0(8) O2 C6 C7 124.3(8) N1 C6 C7 109.7(7) C6 C7 C4 101.8(6) C6 C7 C8 109.5(6) C4 C7 C8 90.3(5) C9 C8 C3 104.8(6) C9 C8 C7 113.5(6) C3 C8 C7 88.7(5) C1 C9 C8 106.0(6) O3 C10 O4 119.7(9) O3 C10 C1 130.4(9) O4 C10 C1 109.9(8) N1 C12 C13 111.7(6) C14 C13 C18 120.1(8) C14 C13 C12 123.0(7) C18 C13 C12 115.9(7) C13 C14 C15 121.0(8) C14 C15 C16 120.9(8) C15 C16 C17 116.2(8) C18 C17 C16 121.1(8) C13 C18 C17 120.1(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C5 1.258(8) O2 C6 1.232(9) O3 C10 1.186(8) O4 C10 1.352(10) O4 C11 1.447(11) N1 C5 1.342(9) N1 C6 1.372(10) N1 C12 1.482(9) C1 C10 1.487(12) C1 C2 1.489(8) C1 C9 1.550(11) C2 C3 1.543(9) C3 C4 1.553(10) C3 C8 1.561(9) C4 C5 1.470(10) C4 C7 1.541(10) C6 C7 1.526(10) C7 C8 1.577(10) C8 C9 1.554(10) C12 C13 1.518(11) C13 C14 1.351(10) C13 C18 1.361(11) C14 C15 1.368(10) C15 C16 1.395(10) C16 C17 1.416(10) C17 C18 1.368(12) 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 C10 C1 C2 C3 87.6(8) C9 C1 C2 C3 -38.7(8) C1 C2 C3 C4 -69.7(9) C1 C2 C3 C8 28.9(9) C2 C3 C4 C5 -142.0(7) C8 C3 C4 C5 110.1(7) C2 C3 C4 C7 111.3(6) C8 C3 C4 C7 3.4(5) C6 N1 C5 O1 179.8(8) C12 N1 C5 O1 -4.8(13) C6 N1 C5 C4 -4.3(9) C12 N1 C5 C4 171.2(7) C7 C4 C5 O1 -176.8(8) C3 C4 C5 O1 86.2(10) C7 C4 C5 N1 7.4(9) C3 C4 C5 N1 -89.5(8) C5 N1 C6 O2 179.0(8) C12 N1 C6 O2 3.4(13) C5 N1 C6 C7 -0.8(9) C12 N1 C6 C7 -176.5(6) O2 C6 C7 C4 -174.7(8) N1 C6 C7 C4 5.2(8) O2 C6 C7 C8 -80.1(9) N1 C6 C7 C8 99.7(7) C5 C4 C7 C6 -7.2(8) C3 C4 C7 C6 106.6(6) C5 C4 C7 C8 -117.2(6) C3 C4 C7 C8 -3.4(5) C2 C3 C8 C9 -7.1(8) C4 C3 C8 C9 110.7(6) C2 C3 C8 C7 -121.2(6) C4 C3 C8 C7 -3.3(5) C6 C7 C8 C9 155.1(6) C4 C7 C8 C9 -102.2(6) C6 C7 C8 C3 -99.3(6) C4 C7 C8 C3 3.3(5) C10 C1 C9 C8 -94.8(8) C2 C1 C9 C8 34.1(8) C3 C8 C9 C1 -16.1(8) C7 C8 C9 C1 79.0(8) C11 O4 C10 O3 -2.4(11) C11 O4 C10 C1 -179.4(7) C2 C1 C10 O3 -127.4(9) C9 C1 C10 O3 -6.4(12) C2 C1 C10 O4 49.3(9) C9 C1 C10 O4 170.2(6) C5 N1 C12 C13 86.0(9) C6 N1 C12 C13 -99.0(9) N1 C12 C13 C14 45.7(11) N1 C12 C13 C18 -145.7(7) C18 C13 C14 C15 6.7(13) C12 C13 C14 C15 174.9(8) C13 C14 C15 C16 -5.4(13) C14 C15 C16 C17 4.3(12) C15 C16 C17 C18 -5.0(12) C14 C13 C18 C17 -7.3(13) C12 C13 C18 C17 -176.3(8) C16 C17 C18 C13 6.6(13)