#------------------------------------------------------------------------------ #$Date: 2024-05-06 07:19:39 +0300 (Mon, 06 May 2024) $ #$Revision: 291717 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/02/30/2023077.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_2023077 loop_ _publ_author_name 'Businski, Artjom' 'Ta, Thuy C.' 'Gindullis, Niklas' 'Näther, Christian' 'Herges, Rainer' _publ_section_title ; Synthesis and crystal structure of tetra-methyl (E)-4,4'-(ethene-1,2-di-yl)bis-(5-nitro-benzene-1,2-di-carboxyl-ate). ; _journal_coeditor_code WM5712 _journal_issue 'Pt 4' _journal_name_full 'Acta crystallographica. Section E, Crystallographic communications' _journal_page_first 435 _journal_page_last 438 _journal_paper_doi 10.1107/S2056989024002676 _journal_volume 80 _journal_year 2024 _chemical_formula_iupac 'C22 H18 N2 O12' _chemical_formula_moiety 'C22 H18 N2 O12' _chemical_formula_sum 'C22 H18 N2 O12' _chemical_formula_weight 502.38 _chemical_name_systematic ; Tetramethyl (E)-4,4'-(ethene-1,2-diyl)bis(5-nitrobenzene-1,2-dicarboxylate) ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_method ; Olex2 1.3-ac4 (compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214) ; _cell_angle_alpha 72.124(3) _cell_angle_beta 79.661(3) _cell_angle_gamma 86.052(3) _cell_formula_units_Z 1 _cell_length_a 5.9454(2) _cell_length_b 7.9543(3) _cell_length_c 12.0673(4) _cell_measurement_reflns_used 3255 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 78.7870 _cell_measurement_theta_min 3.8830 _cell_volume 534.25(3) _computing_cell_refinement ; CrysAlisPro (Rigaku OD, 2022) ; _computing_data_collection ; CrysAlisPro (Rigaku OD, 2022) ; _computing_data_reduction ; CrysAlisPro (Rigaku OD, 2022) ; _computing_molecular_graphics ; DIAMOND (Brandenburg & Putz, 1999) and XP in SHELXTL-PC (Sheldrick, 2008) ; _computing_publication_material ; publCIF (Westrip, 2010) ; _computing_structure_refinement ; SHELXL (Sheldrick, 2015b) ; _computing_structure_solution ; SHELXT (Sheldrick, 2015a) ; _diffrn_ambient_temperature 100.00(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.946 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_unetI/netI 0.0255 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 5274 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 80.114 _diffrn_reflns_theta_min 3.904 _diffrn_source 'micro-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 1.120 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.79073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysAlisPro; Rigaku OD, 2022) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.561 _exptl_crystal_description plate _exptl_crystal_F_000 260 _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.371 _refine_diff_density_min -0.301 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 165 _refine_ls_number_reflns 2211 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.087 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0429 _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^)+(0.0710P)^2^+0.2093P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1224 _refine_ls_wR_factor_ref 0.1247 _reflns_number_gt 2042 _reflns_number_total 2211 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file wm5712.cif _cod_data_source_block I _cod_depositor_comments 'Adding full bibliography for 2023077.cif.' _cod_database_code 2023077 _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_hkl_file ; 0 0 1 43677.2 1146.58 11 0 0 2 13287.0 367.173 11 0 0 3 101135. 2664.71 11 0 0 4 6230.37 211.387 11 0 0 5 125448. 3328.51 11 0 0 -6 273.638 75.1082 18 0 0 7 41.5203 37.6209 23 0 0 -7 72.8090 74.2277 18 0 0 8 28502.5 775.341 23 0 0 -8 29149.6 891.235 18 0 0 9 871.037 66.1748 23 0 0 -9 701.541 121.017 12 0 0 -9 785.498 129.508 18 0 0 10 841.417 71.0860 23 0 0 -10 680.257 133.117 18 0 0 11 182.605 56.4169 23 0 0 12 4956.74 167.306 23 0 0 13 296.733 51.2021 27 0 0 14 231.763 34.9619 27 0 0 14 164.783 39.2057 35 0 -1 13 15752.8 426.505 43 0 -1 13 16254.8 425.038 27 0 -1 12 5443.91 175.942 27 0 -1 11 594.691 65.8714 44 0 -1 11 419.157 60.7381 23 0 -1 10 631.748 70.4167 44 0 1 -10 521.422 72.2774 34 0 -1 10 658.823 65.0135 23 0 1 -9 9927.91 300.133 34 0 -1 9 10365.0 300.017 23 0 1 -9 8535.44 400.683 12 0 -1 9 10198.7 301.702 44 0 1 -9 8933.35 404.098 18 0 1 -8 105.101 89.7678 18 0 -1 8 92.0588 46.3019 23 0 1 -7 20486.8 658.011 18 0 -1 7 20586.6 563.331 23 0 -1 6 11277.3 316.178 23 0 -1 5 3884.23 180.792 11 0 -1 4 14184.8 433.663 11 0 -1 3 20431.0 581.202 11 0 -1 2 14607.1 399.521 4 0 -1 2 15019.7 400.911 3 0 -1 2 13654.7 415.005 11 0 -1 1 69566.6 1816.45 4 0 -1 1 66851.8 1817.21 2 0 -1 1 69626.9 1822.82 13 0 -1 1 70386.5 1818.03 3 0 -1 0 30130.0 165.919 11 0 -1 0 30654.9 121.775 15 0 -1 -1 2627.39 91.7655 4 0 -1 -1 2817.69 92.5760 12 0 -1 -1 2889.55 87.0473 14 0 -1 -1 3071.91 96.2242 18 0 -1 -2 71960.4 1890.40 4 0 -1 -2 74012.2 1897.52 12 0 -1 -2 73482.8 1892.41 2 0 1 2 70651.4 1879.64 11 0 -1 -2 72097.6 1891.08 3 0 -1 -3 228866. 6052.09 4 0 -1 -3 230845. 6052.07 3 0 1 3 235479. 6051.35 11 0 1 4 17372.5 486.330 11 0 -1 -5 56971.7 1559.54 18 0 -1 -6 1679.73 126.402 18 0 -1 -7 3535.60 190.815 18 0 1 7 3219.92 109.610 23 0 -1 -8 22545.4 702.067 18 0 1 8 21183.7 584.497 23 0 1 9 8601.30 255.892 23 0 -1 -9 7841.53 363.430 18 0 1 10 1470.29 85.5821 44 0 -1 -10 1373.34 162.474 18 0 -1 -10 1410.89 87.2727 34 0 1 10 1539.66 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3 0 -2 0 169941. 4440.03 13 0 -2 0 168816. 4438.16 2 0 -2 0 168352. 4425.43 11 0 -2 -1 35069.4 955.231 2 0 -2 -1 35196.1 945.163 16 0 -2 -2 5772.47 170.564 14 0 -2 -2 5629.02 190.046 2 0 -2 -2 5440.44 186.500 3 0 -2 -2 5803.30 184.148 12 0 -2 -2 5433.89 186.594 4 0 -2 -3 240127. 6302.84 4 0 -2 -3 243613. 6309.72 18 0 -2 -3 237329. 6302.97 3 0 -2 -3 242012. 6305.75 12 0 -2 -4 328360. 8598.35 18 0 -2 -4 325030. 8596.02 12 0 -2 -4 326419. 8579.75 3 0 -2 -4 331433. 8579.68 4 0 -2 -5 9913.78 331.251 12 0 -2 -5 9855.30 334.930 18 0 -2 -5 9748.63 298.118 4 0 -2 -6 22696.5 688.985 12 0 -2 -6 23321.6 699.912 18 0 -2 -7 49447.7 1404.71 12 0 -2 -8 1240.36 133.530 12 0 2 8 1337.28 66.3455 23 0 -2 -9 50506.0 1484.47 12 0 2 9 50494.3 1345.58 23 0 -2 -10 6787.53 215.433 34 0 2 10 6730.28 213.303 23 0 -2 -10 6437.47 334.574 12 0 2 11 14962.3 420.100 23 0 -2 -11 14703.9 421.587 25 0 2 11 14224.8 419.542 44 0 2 12 9048.88 269.201 44 0 -2 -12 8785.46 265.325 25 0 2 12 8516.90 264.956 23 0 2 13 276.094 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42178.7 1131.68 25 1 -5 -5 17902.3 600.777 16 1 -5 -5 18707.1 601.170 3 1 -5 -5 17155.9 484.972 25 1 -5 -4 21185.7 700.731 17 1 -5 -4 22475.2 708.662 3 1 -5 -3 44979.2 1323.69 17 1 -5 -3 46106.1 1329.13 3 1 -5 -2 2037.30 158.038 17 1 -5 -2 2292.37 159.426 3 1 -5 -1 24010.1 762.800 3 1 -5 0 29054.1 918.687 17 1 -5 0 30325.9 919.150 3 1 -5 1 2155.02 167.865 17 1 -5 1 1994.94 159.951 3 1 -5 2 40003.7 1207.04 17 1 -5 3 774.510 127.393 17 1 -5 3 1075.15 71.0402 39 1 -5 4 7.13625 84.4461 17 1 -5 4 42.7218 51.1013 39 1 -5 5 749.622 69.8026 39 1 -5 5 706.823 75.9228 42 1 -5 6 3539.11 155.912 35 1 -5 6 3274.15 137.496 42 1 -5 7 74.4455 65.4094 35 1 -5 7 88.9903 52.6145 42 1 -5 8 722.976 71.7363 35 1 -5 9 679.357 59.0919 35 1 -5 10 1148.34 53.3903 35 1 -4 -14 4878.30 146.776 36 1 -4 -13 3434.83 121.365 25 1 -4 -12 703.011 57.3795 56 1 -4 -12 625.218 57.5035 50 1 -4 -12 806.385 63.5414 25 1 -4 -11 114.460 55.0908 25 1 -4 -11 126.433 48.5510 56 1 -4 -10 559.444 63.9273 56 1 -4 -9 8236.69 259.943 56 1 -4 -9 7499.90 384.554 16 1 -4 -8 9270.05 408.580 16 1 -4 -7 2988.73 208.214 16 1 -4 -6 8810.20 330.774 3 1 -4 -6 8867.79 362.820 16 1 -4 -5 37251.7 1051.88 3 1 -4 -5 35264.3 1025.68 14 1 -4 -5 36527.9 1074.54 16 1 -4 -4 807.703 105.940 16 1 -4 -4 926.627 97.9499 17 1 -4 -4 915.229 97.3402 3 1 -4 -3 12663.0 424.437 3 1 -4 -3 11791.4 415.012 17 1 -4 -2 17093.9 548.049 17 1 -4 -1 29067.2 867.288 3 1 -4 0-40.3428 61.3957 3 1 -4 1 4348.23 216.741 13 1 -4 1 4443.17 208.026 3 1 -4 2 2292.51 162.873 13 1 -4 2 2039.17 138.615 3 1 -4 3 745.656 97.9875 3 1 -4 3 936.735 122.828 13 1 -4 4 1098.26 130.208 13 1 -4 5 48.1192 92.1934 13 1 -4 6 375.783 60.3292 39 1 -4 6 271.423 99.2299 13 1 -4 7 20222.7 567.394 39 1 -4 7 20627.2 602.226 35 1 -4 8 1167.64 94.4323 35 1 -4 9 10597.5 326.881 35 1 -4 10 22.8185 50.6555 35 1 -4 11 2725.51 96.2875 35 -1 3 14 189.962 35.6170 27 1 -3 -14 216.348 33.7882 36 1 -3 -13 5125.86 164.184 25 -1 3 13 5084.02 158.928 27 -1 3 12 1316.80 73.1751 23 1 -3 -12 1494.81 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405.923 37 -6 -2 0 14425.3 406.081 29 -6 -2 -1 5490.34 179.533 29 -6 -2 -2 1258.86 82.8582 29 -6 -2 -3 549.098 69.7875 29 6 2 3 474.972 55.2070 55 6 2 4 706.350 59.1020 55 6 2 5 2452.71 97.4342 55 6 2 6 84.1082 42.8755 55 -6 -2 -7 3579.50 127.445 29 -6 -2 -8 1240.27 71.1281 29 6 2 9 1843.01 72.5029 40 -6 -2 -9 1895.12 76.2186 45 6 2 10 14284.7 379.990 40 -6 -2 -10 13638.2 380.515 45 6 2 11 168.603 22.6178 40 -6 -2 -11 136.441 26.1347 45 6 3 -4 42.7359 25.9776 55 6 3 -3 555.949 42.6958 55 -6 -3 2 57.0969 40.2445 37 -6 -3 0 14439.8 398.308 29 6 3 0 14287.8 402.345 55 -6 -3 -1 21408.5 580.157 29 6 3 1 21212.5 583.575 55 -6 -3 -2-0.97062 56.7392 29 6 3 2 33.4985 46.6739 55 -6 -3 -3 692.068 55.6585 38 -6 -3 -3 860.010 68.3444 29 6 3 3 850.763 60.6706 55 -6 -3 -4 93.3963 58.6591 29 6 3 4 45.1331 42.6407 55 -6 -3 -5 52.4996 55.8987 29 6 3 5 41.1891 40.9616 55 -6 -3 -6 1603.46 81.5802 29 6 3 6 1535.72 71.1860 55 -6 -3 -7 1458.84 75.2329 29 -6 -3 -7 1176.83 66.2019 45 -6 -3 -8 1509.18 69.4439 9 -6 -3 -8 1866.46 75.1188 45 -6 -3 -9 3676.79 119.298 45 6 3 10 1554.64 60.4657 40 6 3 11 820.669 35.1972 40 -6 -3 -11 694.563 35.0937 45 6 4 -3 52.0479 24.5038 55 -6 -4 2 53.7631 26.6796 41 6 4 -2 26.4736 31.0377 55 -6 -4 1 66.6284 29.4372 41 6 4 -1 68.7282 37.0187 55 -6 -4 0 287.528 40.4974 5 6 4 0 459.846 45.8435 55 -6 -4 -1 4830.11 157.326 38 -6 -4 -1 4716.71 158.123 9 6 4 1 4901.40 152.252 55 -6 -4 -2 475.068 49.8522 38 6 4 2 512.839 51.2809 55 -6 -4 -3 1182.34 66.0381 38 6 4 3 1284.32 65.5977 55 -6 -4 -4 7433.93 227.240 38 -6 -4 -4 7821.85 223.822 29 6 4 4 7687.99 223.553 55 -6 -4 -5 1226.53 63.1871 38 -6 -4 -5 1411.00 71.6039 29 6 4 5 1288.61 62.3236 55 -6 -4 -6 762.590 58.9505 29 6 4 6 695.666 47.1949 55 -6 -4 -7 1426.13 69.2819 9 -6 -4 -7 1515.76 70.6936 29 -6 -4 -8 299.697 37.4930 9 -6 -4 -8 382.949 50.9417 29 -6 -4 -8 306.894 37.0143 45 -6 -4 -9 9251.92 258.886 45 -6 -4 -10 15327.4 412.498 45 -6 -4 -11 24.6709 14.9173 45 6 5 -1 542.106 36.4852 55 -6 -5 0 15.8385 26.4149 41 -6 -5 0 1.47431 28.3870 38 6 5 0 54.8596 32.2075 55 -6 -5 -1 1496.07 65.9605 38 6 5 1 1419.64 62.3568 55 -6 -5 -2 136.535 36.8772 38 -6 -5 -2 113.874 37.6355 5 -6 -5 -2 112.470 35.5978 9 6 5 2 101.388 35.6435 55 -6 -5 -3 5681.41 170.669 38 -6 -5 -3 5380.86 173.077 5 -6 -5 -3 5387.65 173.443 9 6 5 3 5591.29 162.070 55 -6 -5 -4 175.131 37.7955 38 -6 -5 -4 93.7368 36.1976 5 6 5 4 138.351 34.8438 55 -6 -5 -5 62.9910 35.1701 38 -6 -5 -5 77.8819 39.0776 9 6 5 5 65.1001 32.9182 55 -6 -5 -6 636.294 47.0457 5 -6 -5 -6 585.468 48.2950 9 -6 -5 -7 59.2467 29.7349 5 -6 -5 -7 54.7656 36.8144 9 -6 -5 -8 2477.76 84.4734 9 -6 -5 -9 148.080 23.3150 26 6 5 10 2743.94 82.3763 40 -6 -6 -2 34.0817 25.6577 38 -6 -6 -3 734.205 42.7300 38 -6 -6 -3 695.451 41.7652 9 -6 -6 -4 114.285 30.1760 38 -6 -6 -5 812.770 45.4118 9 -6 -6 -6 2638.44 89.3814 9 -6 -6 -7 1166.30 51.1567 9 -6 -6 -7 1368.10 53.6549 26 -6 -6 -8 323.039 28.6983 26 7 -3 1 86.6105 18.2379 10 7 -3 2 295.438 21.2852 10 7 -3 2 267.408 19.0304 30 7 -2 -1 293.692 25.1335 10 7 -2 -1 324.141 25.5005 8 -7 2 1 335.482 33.1140 29 7 -2 0 2178.18 70.7231 10 7 -2 0 2109.63 70.0149 8 -7 2 0 2013.52 66.0223 29 7 -2 1 3792.98 114.116 30 7 -2 2 1981.09 72.6888 10 7 -2 2 2099.53 70.5453 30 7 -2 2 2046.99 72.4308 8 7 -2 3 586.403 35.2344 10 7 -2 3 556.149 34.4006 8 7 -2 4 764.525 36.0171 10 7 -2 4 861.484 37.5527 8 7 -2 5 1436.23 48.1622 30 -7 1 3 405.633 29.2839 29 -7 1 2 209.538 36.8811 29 7 -1 -1 739.291 38.8129 10 7 -1 -1 698.966 37.3156 8 7 -1 0-0.61296 24.4399 30 -7 1 0 72.0048 40.1815 29 7 -1 0 24.5189 25.5618 8 7 -1 1 80.6859 31.0165 6 7 -1 1 16.2283 27.4092 30 -7 1 -1 33.4695 44.3469 29 7 -1 1 36.1680 28.5224 24 -7 1 -2 6192.17 171.524 29 7 -1 2 5695.39 174.475 8 7 -1 2 5634.12 174.753 6 7 -1 3 474.442 36.4937 30 -7 1 -3 481.059 49.0081 29 7 -1 3 429.196 36.6968 8 7 -1 3 433.556 34.1088 24 7 -1 3 375.248 34.5594 6 7 -1 4 9.03648 25.3440 30 -7 1 -4 5.04579 37.6598 29 7 -1 4 21.2635 26.4041 8 7 -1 5 235.452 24.5296 10 7 -1 5 255.958 28.5392 30 7 -1 5 247.497 24.5670 8 7 -1 6 902.003 36.6296 30 -7 0 1 82.3513 37.1546 29 -7 0 0 420.324 45.7355 29 7 0 0 315.469 32.8265 8 -7 0 -1 207.397 45.6689 29 -7 0 -2 8684.21 242.478 29 7 0 2 8471.23 237.510 55 -7 0 -3 1089.95 58.9901 29 7 0 4 1406.64 62.1892 30 -7 0 -4 1669.83 67.3958 29 7 0 5 391.408 33.8939 30 -7 0 -5 469.868 45.1367 29 7 0 5 348.415 34.0329 8 7 0 6 2280.84 78.5512 10 7 0 6 2349.83 78.9443 8 -7 0 -7 745.518 35.1873 45 -7 -1 2 1924.17 65.5198 29 -7 -1 1 115.640 34.9590 29 7 1 0 50.0614 26.2832 55 7 1 1 1335.64 54.8625 55 7 1 2 680.422 42.3177 55 -7 -1 -3 821.783 55.2378 29 7 1 3 842.014 45.4262 55 -7 -1 -4 150.115 43.7371 29 7 1 4 178.597 33.4020 55 7 1 5 72.4098 30.6164 30 -7 -1 -5 66.9545 39.9189 29 7 1 6 42.3063 25.2652 30 -7 -1 -6 51.7256 36.1339 29 -7 -1 -7 344.367 39.2801 29 -7 -1 -7 308.820 27.9454 45 7 2 -1 13081.7 349.660 55 -7 -2 0 219.005 35.8280 29 7 2 0 257.834 27.8405 55 -7 -2 -1 43.3392 38.0276 29 7 2 1 81.2877 27.9961 55 -7 -2 -2 92.7882 40.3874 29 -7 -2 -3 248.411 42.6771 29 7 2 4 679.070 41.4536 55 7 2 6 1257.81 47.9833 30 -7 -2 -7 88.9174 32.6512 29 -7 -2 -7 86.1806 21.6993 45 -7 -2 -8 3294.06 94.8929 45 7 3 1 259.185 27.0994 55 -7 -3 -2 4501.85 149.631 9 7 3 2 5487.31 145.997 55 7 3 3 3084.87 95.5477 55 -7 -3 -4 1099.92 51.1809 29 7 3 4 1072.27 46.5029 55 -7 -3 -5 377.034 35.3040 9 -7 -3 -5 432.616 38.7483 29 -7 -3 -6 152.458 28.0052 9 -7 -3 -6 201.691 33.0040 29 7 4 2 135.184 19.9872 55 -7 -4 -3 108.397 22.1481 9 7 4 3 152.083 23.8870 55 7 4 4 703.359 33.5495 55 -7 -4 -5 209.698 26.6459 9 -7 -4 -6 11.0501 18.2582 9 0 0 0 0.00 0.00 0 TITL Herges176_auto in P-1 REM P-1 (#2 in standard setting) CELL 1.54184 5.945394 7.954262 12.067305 72.1244 79.6615 86.0523 ZERR 1.00 0.000224 0.000256 0.000422 0.0031 0.0032 0.0028 LATT 1 SFAC C H N O UNIT 22.00 18.00 2.00 12.00 REM CrysAlisPro recorded range (K): Min=100.0; max=100.1; aver:100.0 TEMP -173 TREF HKLF 4 END ; _shelx_hkl_checksum 17098 _shelx_res_file ; TITL herges176_a.res in P-1 herges176.res created by SHELXL-2016/6 at 19:04:49 on 02-Feb-2024 REM Old TITL Herges176_auto in P-1 REM SHELXT solution in P-1 REM R1 0.113, Rweak 0.006, Alpha 0.076, Orientation as input REM Formula found by SHELXT: C11 N O6 CELL 1.54184 5.945394 7.954262 12.067305 72.1244 79.6615 86.0523 ZERR 1 0.000224 0.000256 0.000422 0.0031 0.0032 0.0028 LATT 1 SFAC C H N O UNIT 22 18 2 12 EQIV $1 1-X,-Y,2-Z EQIV $2 +X,-1+Y,+Z EQIV $3 1+X,+Y,+Z L.S. 10 PLAN 5 TEMP -173 HTAB C9 O5_$1 HTAB C11 O3_$2 HTAB C11 O5_$3 MPLA C2 C3 C4 C5 C6 MPLA N1 O1 O2 MPLA C8 O3 O4 MPLA C10 O5 O6 BOND $H HTAB list 6 fmap 2 53 acta REM REM REM WGHT 0.071000 0.209300 FVAR 9.43017 C1 1 0.035915 0.572094 0.512411 11.00000 0.02920 0.02379 = 0.03938 -0.01704 -0.01674 0.00827 AFIX 43 H1 2 -0.031345 0.684945 0.481716 11.00000 -1.20000 AFIX 0 C2 1 0.216662 0.553716 0.586336 11.00000 0.02552 0.02140 = 0.02761 -0.01276 -0.00895 0.00477 C3 1 0.315850 0.698109 0.602460 11.00000 0.02726 0.01724 = 0.02678 -0.00994 -0.00883 0.00602 C4 1 0.471101 0.680737 0.678719 11.00000 0.02685 0.01864 = 0.02794 -0.01101 -0.00876 0.00208 AFIX 43 H4 2 0.530524 0.782718 0.687774 11.00000 -1.20000 AFIX 0 C5 1 0.538855 0.513619 0.741569 11.00000 0.02427 0.02070 = 0.02638 -0.00999 -0.00815 0.00346 C6 1 0.450635 0.365888 0.725505 11.00000 0.02554 0.01885 = 0.02764 -0.00932 -0.00817 0.00327 C7 1 0.290094 0.386832 0.650941 11.00000 0.02676 0.01874 = 0.03160 -0.01244 -0.01046 0.00296 AFIX 43 H7 2 0.228245 0.284508 0.643620 11.00000 -1.20000 AFIX 0 N1 3 0.261008 0.881057 0.537582 11.00000 0.02761 0.01960 = 0.03189 -0.01066 -0.01171 0.00460 O1 4 0.265733 0.994882 0.586985 11.00000 0.03958 0.01964 = 0.04553 -0.01693 -0.01851 0.00803 O2 4 0.221966 0.912521 0.437211 11.00000 0.04185 0.02615 = 0.03261 -0.00705 -0.01826 0.00384 C8 1 0.696567 0.500146 0.828105 11.00000 0.02816 0.01665 = 0.02889 -0.01096 -0.01049 0.00534 O3 4 0.860163 0.593045 0.808158 11.00000 0.03086 0.02262 = 0.03555 -0.01015 -0.01378 0.00048 O4 4 0.627971 0.376629 0.930053 11.00000 0.03271 0.02016 = 0.02722 -0.00693 -0.01262 0.00163 C9 1 0.782607 0.341121 1.015035 11.00000 0.03665 0.02654 = 0.03108 -0.00851 -0.01706 0.00452 AFIX 137 H9A 2 0.933156 0.306373 0.979732 11.00000 -1.50000 H9B 2 0.722258 0.245232 1.085262 11.00000 -1.50000 H9C 2 0.796944 0.447755 1.037561 11.00000 -1.50000 AFIX 0 C10 1 0.526710 0.181109 0.784642 11.00000 0.03059 0.01926 = 0.03191 -0.00943 -0.01366 0.00212 O5 4 0.398966 0.058335 0.825059 11.00000 0.03861 0.02226 = 0.06048 -0.00176 -0.02457 -0.00230 O6 4 0.750632 0.170461 0.783932 11.00000 0.02971 0.01854 = 0.03332 -0.00973 -0.01288 0.00656 C11 1 0.837390 -0.002497 0.843837 11.00000 0.03726 0.01997 = 0.04427 -0.00844 -0.01733 0.00991 AFIX 137 H11A 2 0.806798 -0.087882 0.804802 11.00000 -1.50000 H11B 2 0.761355 -0.039755 0.926402 11.00000 -1.50000 H11C 2 1.002594 0.003374 0.840751 11.00000 -1.50000 AFIX 0 HKLF 4 REM herges176_a.res in P-1 REM R1 = 0.0429 for 2042 Fo > 4sig(Fo) and 0.0458 for all 2211 data REM 165 parameters refined using 0 restraints END WGHT 0.0710 0.2092 REM Instructions for potential hydrogen bonds HTAB C9 O5_$1 HTAB C11 O3_$2 HTAB C11 O5_$3 REM Highest difference peak 0.371, deepest hole -0.301, 1-sigma level 0.055 Q1 1 -0.0881 0.6559 0.5315 11.00000 0.05 0.37 Q2 1 0.1217 0.6592 0.4235 11.00000 0.05 0.35 Q3 1 0.6133 0.5013 0.7837 11.00000 0.05 0.28 Q4 1 0.2597 0.6334 0.5954 11.00000 0.05 0.27 Q5 1 0.1385 0.5642 0.5452 11.00000 0.05 0.24 ; _shelx_res_checksum 54454 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 _atom_site_disorder_assembly _atom_site_disorder_group C C1 0.0359(3) 0.5721(2) 0.51241(15) 0.0281(3) Uani d 1 . . H H1 -0.031345 0.684945 0.481716 0.034 Uiso calc 1 . . C C2 0.2167(3) 0.55372(19) 0.58634(13) 0.0233(3) Uani d 1 . . C C3 0.3159(3) 0.69811(19) 0.60246(13) 0.0227(3) Uani d 1 . . C C4 0.4711(3) 0.6807(2) 0.67872(13) 0.0231(3) Uani d 1 . . H H4 0.530524 0.782718 0.687774 0.028 Uiso calc 1 . . C C5 0.5389(3) 0.5136(2) 0.74157(13) 0.0228(3) Uani d 1 . . C C6 0.4506(3) 0.36589(19) 0.72551(13) 0.0232(3) Uani d 1 . . C C7 0.2901(3) 0.3868(2) 0.65094(14) 0.0240(3) Uani d 1 . . H H7 0.228245 0.284508 0.643620 0.029 Uiso calc 1 . . N N1 0.2610(2) 0.88106(17) 0.53758(12) 0.0251(3) Uani d 1 . . O O1 0.2657(2) 0.99488(15) 0.58698(11) 0.0322(3) Uani d 1 . . O O2 0.2220(2) 0.91252(15) 0.43721(11) 0.0326(3) Uani d 1 . . C C8 0.6966(3) 0.50015(19) 0.82811(13) 0.0232(3) Uani d 1 . . O O3 0.8602(2) 0.59305(14) 0.80816(10) 0.0283(3) Uani d 1 . . O O4 0.62797(19) 0.37663(14) 0.93005(9) 0.0258(3) Uani d 1 . . C C9 0.7826(3) 0.3411(2) 1.01503(15) 0.0302(4) Uani d 1 . . H H9A 0.933156 0.306373 0.979732 0.045 Uiso calc 1 . . H H9B 0.722258 0.245232 1.085262 0.045 Uiso calc 1 . . H H9C 0.796944 0.447755 1.037561 0.045 Uiso calc 1 . . C C10 0.5267(3) 0.1811(2) 0.78464(14) 0.0259(3) Uani d 1 . . O O5 0.3990(2) 0.05833(16) 0.82506(13) 0.0407(3) Uani d 1 . . O O6 0.75063(19) 0.17046(14) 0.78393(10) 0.0261(3) Uani d 1 . . C C11 0.8374(3) -0.0025(2) 0.84384(17) 0.0332(4) Uani d 1 . . H H11A 0.806798 -0.087882 0.804802 0.050 Uiso calc 1 . . H H11B 0.761355 -0.039755 0.926402 0.050 Uiso calc 1 . . H H11C 1.002594 0.003374 0.840751 0.050 Uiso calc 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0292(8) 0.0238(8) 0.0394(9) 0.0083(6) -0.0167(7) -0.0170(6) C2 0.0255(7) 0.0214(7) 0.0276(7) 0.0048(5) -0.0089(6) -0.0128(6) C3 0.0273(7) 0.0172(7) 0.0268(7) 0.0060(5) -0.0088(6) -0.0099(5) C4 0.0268(7) 0.0186(7) 0.0279(7) 0.0021(5) -0.0088(6) -0.0110(6) C5 0.0243(7) 0.0207(7) 0.0264(7) 0.0035(5) -0.0081(6) -0.0100(6) C6 0.0255(7) 0.0188(7) 0.0276(7) 0.0033(5) -0.0082(6) -0.0093(6) C7 0.0268(7) 0.0187(7) 0.0316(8) 0.0030(5) -0.0105(6) -0.0124(6) N1 0.0276(6) 0.0196(6) 0.0319(7) 0.0046(5) -0.0117(5) -0.0107(5) O1 0.0396(7) 0.0196(6) 0.0455(7) 0.0080(4) -0.0185(5) -0.0169(5) O2 0.0418(7) 0.0262(6) 0.0326(6) 0.0038(5) -0.0183(5) -0.0071(5) C8 0.0282(7) 0.0166(7) 0.0289(7) 0.0053(5) -0.0105(6) -0.0110(6) O3 0.0309(6) 0.0226(6) 0.0356(6) 0.0005(4) -0.0138(5) -0.0102(4) O4 0.0327(6) 0.0202(5) 0.0272(5) 0.0016(4) -0.0126(4) -0.0069(4) C9 0.0366(8) 0.0265(8) 0.0311(8) 0.0045(6) -0.0171(7) -0.0085(6) C10 0.0306(8) 0.0193(7) 0.0319(8) 0.0021(6) -0.0137(6) -0.0094(6) O5 0.0386(7) 0.0223(6) 0.0605(8) -0.0023(5) -0.0246(6) -0.0018(5) O6 0.0297(6) 0.0185(5) 0.0333(6) 0.0066(4) -0.0129(4) -0.0097(4) C11 0.0373(9) 0.0200(8) 0.0443(9) 0.0099(6) -0.0173(7) -0.0084(7) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 C1 H1 2_566 . 119.4 ? C1 C1 C2 2_566 . 121.20(18) ? C2 C1 H1 . . 119.4 ? C3 C2 C1 . . 123.55(13) ? C7 C2 C1 . . 121.09(13) ? C7 C2 C3 . . 115.26(13) ? C2 C3 N1 . . 121.38(13) ? C4 C3 C2 . . 123.52(13) ? C4 C3 N1 . . 115.10(12) ? C3 C4 H4 . . 120.2 ? C5 C4 C3 . . 119.57(13) ? C5 C4 H4 . . 120.2 ? C4 C5 C6 . . 118.99(13) ? C4 C5 C8 . . 117.98(13) ? C6 C5 C8 . . 122.98(13) ? C5 C6 C10 . . 122.09(13) ? C7 C6 C5 . . 120.29(13) ? C7 C6 C10 . . 117.60(13) ? C2 C7 H7 . . 118.9 ? C6 C7 C2 . . 122.30(13) ? C6 C7 H7 . . 118.9 ? O1 N1 C3 . . 117.41(12) ? O2 N1 C3 . . 118.67(12) ? O2 N1 O1 . . 123.86(13) ? O3 C8 C5 . . 123.87(14) ? O3 C8 O4 . . 124.94(14) ? O4 C8 C5 . . 111.17(13) ? C8 O4 C9 . . 115.16(12) ? O4 C9 H9A . . 109.5 ? O4 C9 H9B . . 109.5 ? O4 C9 H9C . . 109.5 ? H9A C9 H9B . . 109.5 ? H9A C9 H9C . . 109.5 ? H9B C9 H9C . . 109.5 ? O5 C10 C6 . . 123.44(14) ? O5 C10 O6 . . 124.79(14) ? O6 C10 C6 . . 111.75(13) ? C10 O6 C11 . . 115.35(12) ? O6 C11 H11A . . 109.5 ? O6 C11 H11B . . 109.5 ? O6 C11 H11C . . 109.5 ? H11A C11 H11B . . 109.5 ? H11A C11 H11C . . 109.5 ? H11B C11 H11C . . 109.5 ? 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 C1 C1 2_566 1.383(3) ? C1 H1 . 0.9500 ? C1 C2 . 1.488(2) ? C2 C3 . 1.406(2) ? C2 C7 . 1.403(2) ? C3 C4 . 1.388(2) ? C3 N1 . 1.4710(19) ? C4 H4 . 0.9500 ? C4 C5 . 1.386(2) ? C5 C6 . 1.398(2) ? C5 C8 . 1.5000(19) ? C6 C7 . 1.394(2) ? C6 C10 . 1.502(2) ? C7 H7 . 0.9500 ? N1 O1 . 1.2316(17) ? N1 O2 . 1.2208(18) ? C8 O3 . 1.2065(19) ? C8 O4 . 1.3335(19) ? O4 C9 . 1.4497(18) ? C9 H9A . 0.9800 ? C9 H9B . 0.9800 ? C9 H9C . 0.9800 ? C10 O5 . 1.202(2) ? C10 O6 . 1.3268(19) ? O6 C11 . 1.4515(18) ? C11 H11A . 0.9800 ? C11 H11B . 0.9800 ? C11 H11C . 0.9800 ? 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 C9 H9B O5 2_657 0.98 2.42 3.308(2) 149.8 C11 H11A O3 1_545 0.98 2.52 3.3650(19) 143.7 C11 H11C O5 1_655 0.98 2.39 3.364(2) 172.6 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 C1 C1 C2 C7 2_566 . . . -11.9(3) ? C1 C1 C2 C3 2_566 . . . 171.9(2) ? C7 C2 C3 C4 . . . . -1.7(2) ? C1 C2 C3 C4 . . . . 174.69(15) ? C7 C2 C3 N1 . . . . 177.99(13) ? C1 C2 C3 N1 . . . . -5.6(2) ? C2 C3 C4 C5 . . . . 1.5(2) ? N1 C3 C4 C5 . . . . -178.24(13) ? C3 C4 C5 C6 . . . . 0.7(2) ? C3 C4 C5 C8 . . . . -176.63(13) ? C4 C5 C6 C7 . . . . -2.5(2) ? C8 C5 C6 C7 . . . . 174.67(14) ? C4 C5 C6 C10 . . . . 176.16(14) ? C8 C5 C6 C10 . . . . -6.6(2) ? C5 C6 C7 C2 . . . . 2.3(2) ? C10 C6 C7 C2 . . . . -176.45(14) ? C3 C2 C7 C6 . . . . -0.2(2) ? C1 C2 C7 C6 . . . . -176.69(14) ? C4 C3 N1 O2 . . . . 146.08(15) ? C2 C3 N1 O2 . . . . -33.6(2) ? C4 C3 N1 O1 . . . . -31.3(2) ? C2 C3 N1 O1 . . . . 148.99(15) ? C4 C5 C8 O3 . . . . -43.2(2) ? C6 C5 C8 O3 . . . . 139.53(16) ? C4 C5 C8 O4 . . . . 134.90(14) ? C6 C5 C8 O4 . . . . -42.34(19) ? O3 C8 O4 C9 . . . . -8.0(2) ? C5 C8 O4 C9 . . . . 173.88(12) ? C7 C6 C10 O5 . . . . -40.6(2) ? C5 C6 C10 O5 . . . . 140.64(18) ? C7 C6 C10 O6 . . . . 137.89(15) ? C5 C6 C10 O6 . . . . -40.8(2) ? O5 C10 O6 C11 . . . . -4.0(2) ? C6 C10 O6 C11 . . . . 177.52(13) ?