#------------------------------------------------------------------------------ #$Date: 2024-03-05 21:44:39 +0100 (Tue, 05 Mar 2024) $ #$Revision: 290339 $ #$URL: svn://www.crystallography.net/cod/cif/2/02/30/2023010.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_2023010 loop_ _publ_author_name 'Bibik, Yurii S.' 'Khomenko, Dmytro M.' 'Doroshchuk, Roman O.' 'Raspertova, Ilona V.' 'Bargan, Alexandra' 'Lampeka, Rostyslav D.' _publ_section_title ; Synthesis and crystal structure of N1,N2-di-methyl-ethane-dihydrazide. ; _journal_coeditor_code VM2294 _journal_issue 'Pt 2' _journal_name_full 'Acta crystallographica. Section E, Crystallographic communications' _journal_page_first 148 _journal_page_last 151 _journal_paper_doi 10.1107/S2056989024000239 _journal_volume 80 _journal_year 2024 _chemical_absolute_configuration unk _chemical_formula_iupac 'C4 H10 N4 O2' _chemical_formula_moiety 'C4 H10 N4 O2' _chemical_formula_sum 'C4 H10 N4 O2' _chemical_formula_weight 146.16 _chemical_name_systematic ; N^1^,N^2^-Dimethylethanedihydrazide ; _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 dual _audit_creation_method ; Olex2 1.5-ac5-024 (compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498) ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.0356(5) _cell_length_b 7.6501(6) _cell_length_c 15.7851(14) _cell_measurement_reflns_used 809 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 21.4460 _cell_measurement_theta_min 2.5740 _cell_volume 728.84(11) _computing_cell_refinement ; CrysAlisPro 1.171.38.41 (Rigaku OD, 2021) ; _computing_data_collection ; CrysAlisPro 1.171.38.41 (Rigaku OD, 2021) ; _computing_data_reduction ; CrysAlisPro 1.171.38.41 (Rigaku OD, 2021) ; _computing_molecular_graphics ; Olex2 1.5-ac5-024 (Dolomanov et al., 2009) ; _computing_publication_material ; Olex2 1.5-ac5-024 (Dolomanov et al., 2009) ; _computing_structure_refinement ; SHELXL2018/3 (Sheldrick, 2015b) ; _computing_structure_solution ; SHELXT (Sheldrick, 2015a) ; _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 8.0797 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_unetI/netI 0.0595 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 2356 _diffrn_reflns_theta_full 25.011 _diffrn_reflns_theta_max 25.011 _diffrn_reflns_theta_min 2.581 _diffrn_source 'fine-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.97469 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysAlisPro; Rigaku OD, 2021) ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_density_diffrn 1.332 _exptl_crystal_description prism _exptl_crystal_F_000 312 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.142 _refine_diff_density_min -0.115 _refine_ls_abs_structure_details ; Flack x determined using 280 quotients [(I^+^)-(I^-^)]/[(I^+^)+(I^-^)] (Parsons et al., 2013) ; _refine_ls_abs_structure_Flack -0.7(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 107 _refine_ls_number_reflns 1279 _refine_ls_number_restraints 6 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_all 0.0680 _refine_ls_R_factor_gt 0.0497 _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^)+(0.0311P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0846 _refine_ls_wR_factor_ref 0.0932 _reflns_number_gt 1014 _reflns_number_total 1279 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file vm2294sup1.cif _cod_data_source_block I _cod_depositor_comments 'Adding full bibliography for 2023010.cif.' _cod_original_cell_volume 728.84(10) _cod_database_code 2023010 _cod_database_fobs_code 2023010 _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 -2 14236.4 562.420 2 0 0 2 14845.6 571.674 2 0 0 2 14260.8 634.003 1 0 0 -2 14292.3 631.602 1 0 0 3 185.425 142.491 1 0 0 -3 330.145 150.022 2 0 0 3 266.073 133.413 2 0 0 -3 438.754 189.296 1 0 0 -4 43220.0 1377.23 2 0 0 -4 44015.8 1568.82 1 0 0 4 43637.8 1552.81 1 0 0 4 43962.7 1393.15 2 0 0 5-64.9935 116.789 2 0 0 5 323.324 234.470 1 0 0 -5-37.7679 154.204 1 0 0 6 319414. 5192.33 1 0 0 6 331867. 4710.87 2 0 0 -6 322515. 5238.72 1 0 0 7 420.933 367.571 1 0 0 7 224.830 245.803 2 0 0 -7-146.805 170.457 1 0 0 8 100992. 3057.87 2 0 0 8 104189. 3464.34 1 0 0 9 331.659 272.168 2 0 0 9-139.205 174.642 1 0 0 10 23514.5 1881.09 1 0 0 11 333.626 314.005 1 0 0 12 1644.63 581.011 1 0 0 13-119.079 351.984 1 0 0 14 1015.46 598.351 1 0 0 15-63.5984 337.534 1 0 0 16 1908.73 694.184 1 0 0 17 566.227 548.848 1 0 0 18 9707.29 1706.99 1 0 0 19 401.574 438.418 1 0 1 0 18.2357 57.5133 1 0 -1 -1 94296.8 1451.64 1 0 1 1 94806.4 1444.43 1 0 1 -1 96746.5 1671.66 2 0 1 -2 607361. 4876.90 2 0 1 -2 609284. 4661.97 1 0 -1 -2 614722. 4381.61 1 0 1 2 600844. 4283.22 1 0 -1 2 615800. 4919.66 2 0 1 3 243.253 153.532 1 0 1 -3-106.569 127.354 1 0 -1 3 90.9631 113.751 2 0 1 -3 158.747 131.974 2 0 -1 -3 44.8355 95.9880 1 0 -1 3 81.5473 131.672 1 0 1 4 255021. 3801.33 1 0 1 -4 251536. 3989.29 1 0 -1 4 253845. 3936.05 2 0 1 -4 250676. 3920.68 2 0 -1 -4 251513. 3774.46 1 0 -1 4 251473. 3961.72 1 0 -1 -5 198588. 3755.23 1 0 1 5 196793. 3705.39 1 0 -1 5 201233. 3794.61 2 0 -1 5 193919. 3846.58 1 0 1 -5 199389. 3917.61 1 0 1 -5 197093. 3800.19 2 0 1 6 106170. 2981.25 1 0 -1 -6 112912. 3136.20 1 0 -1 6 112425. 3207.19 1 0 1 -6 105724. 2989.20 2 0 1 6 109412. 2437.48 2 0 1 -6 107156. 3102.41 1 0 -1 6 105496. 2972.40 2 0 -1 7 131.898 218.569 2 0 1 -7 180.306 129.870 1 0 -1 7 184.717 239.046 1 0 1 7 336.180 182.564 2 0 1 -7 90.0974 233.560 2 0 -1 -7 431.720 311.250 1 0 1 7-3.71813 209.556 1 0 -1 8 533.763 334.299 2 0 1 8 565.965 298.473 1 0 -1 8 222.213 244.744 1 0 1 -8 197.130 180.404 2 0 1 8 737.122 269.290 2 0 1 9 34268.3 1744.31 2 0 1 -9 35146.5 2071.89 2 0 1 9 36377.3 2154.73 1 0 -1 9 36753.4 2246.98 1 0 1 10 210.484 192.024 2 0 1 10-54.7798 231.123 1 0 -1 10 393.186 330.869 1 0 -1 11 1598.50 576.068 1 0 1 11 1748.19 582.442 1 0 1 12 6380.75 1099.05 1 0 -1 12 6835.94 1176.25 1 0 -1 13 14085.3 1707.30 1 0 1 13 14956.2 1723.62 1 0 1 14-24.1645 313.126 1 0 -1 14 331.807 446.426 1 0 1 15 573.219 483.027 1 0 -1 15 217.202 415.943 1 0 1 16 1296.75 630.522 1 0 -1 16 775.127 390.317 1 0 1 17 1859.77 791.171 1 0 -1 17 986.840 562.203 1 0 1 18 3052.30 1044.30 1 0 1 19 3353.18 1117.62 1 0 1 20 5099.27 1378.51 1 0 2 0 5822.99 494.091 1 0 -2 -1 436359. 4202.04 1 0 2 1 438030. 4164.94 1 0 -2 -2 18050.1 899.806 1 0 2 -2 18007.3 1051.51 2 0 2 2 17192.8 881.207 1 0 -2 -3 83520.9 2106.37 1 0 2 3 86836.2 2129.71 1 0 2 -3 83973.1 2431.97 2 0 -2 4 160334. 3598.57 2 0 -2 -4 161501. 3215.91 1 0 2 -4 160097. 3616.92 2 0 2 4 160236. 3152.44 1 0 2 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0-19.3655 167.385 1 0 5 -1 19662.3 1565.25 2 0 5 -1 17898.1 1400.69 1 0 5 1 20867.7 1455.36 1 0 5 2 13290.6 1159.53 1 0 5 -2 12250.9 1185.64 1 0 5 -2 12020.8 1247.70 2 0 5 -3 878.095 365.422 1 0 5 3 898.944 326.537 1 0 5 -3 1966.54 571.618 2 0 -5 -3 2564.95 539.219 1 0 -5 -4 12917.5 1194.50 1 0 5 4 13378.2 1211.09 1 0 5 -4 13287.9 1446.56 2 0 5 -5 108536. 4208.81 2 0 5 5 100287. 3378.03 1 0 5 -6 37310.7 2624.39 2 0 5 6 35571.8 2080.38 1 0 5 -7 8883.54 1335.67 2 0 5 7 11099.4 1216.18 1 0 5 -8 10661.5 1469.61 2 0 5 8 9952.64 1205.88 1 0 5 -9 12319.2 1640.60 2 0 5 9 12544.6 1411.12 1 0 5 -10 4757.42 1097.03 2 0 5 10 5402.14 1002.99 1 0 5 11 5893.75 1050.00 1 0 5 -11 5649.03 1219.76 2 0 5 12 9265.51 1365.46 1 0 5 -12 7606.01 1504.59 2 0 5 -13 3541.84 1131.02 2 0 5 13 3202.85 831.551 1 0 5 -14 1866.55 793.131 2 0 5 14 2453.56 783.230 1 0 5 -15 3150.98 1020.16 2 0 5 15 2904.88 905.354 1 0 5 16 1018.24 531.862 1 0 5 17 429.224 638.555 1 0 5 18 404.716 467.522 1 0 6 0 308.205 277.511 1 0 6 0 57.0797 174.699 2 0 6 1 2296.02 574.413 2 0 6 -1 2429.54 576.036 1 0 6 1 1660.53 479.365 1 0 6 -1 2351.13 662.468 2 0 6 2 273.327 255.128 1 0 6 2 599.479 402.307 2 0 6 -2 923.908 451.325 1 0 6 -2 162.358 193.938 2 0 6 -3 10478.5 1340.28 2 0 6 -3 8630.95 1127.26 1 0 6 3 10454.3 1134.33 1 0 6 -4 13740.8 1474.75 1 0 6 -4 15346.5 1665.07 2 0 6 4 15725.8 1419.50 1 0 6 5 3251.57 675.906 1 0 6 -5 2096.75 694.930 2 0 6 -6 312.050 355.681 2 0 6 6 630.964 373.535 1 0 6 -7 3028.22 874.683 2 0 6 7 1435.02 503.980 1 0 6 -8 18708.0 2126.86 2 0 6 8 20630.0 1811.36 1 0 6 -9 13369.8 1854.71 2 0 6 9 14832.1 1589.16 1 0 6 10 6225.02 1114.05 1 0 6 -10 5769.21 1275.18 2 0 6 -11 978.023 730.240 2 0 6 11 2216.26 720.856 1 0 6 12 2585.74 742.377 1 0 6 -12 2423.22 881.804 2 0 6 13 10660.0 1545.32 1 0 6 -13 5994.83 1478.73 2 0 6 14 11410.3 1661.52 1 0 6 -14 12352.2 2046.02 2 0 6 15 706.045 584.172 1 0 6 -15 600.264 669.808 2 0 7 0 733.021 418.871 1 0 7 0 243.803 361.287 2 0 7 -1 9965.49 1337.30 2 0 7 1 9719.38 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1028.35 1 3 7 7 64.3488 377.539 1 3 7 8 960.063 777.891 1 3 7 9 751.045 569.952 1 3 7 10 871.945 588.488 1 3 7 11 1652.01 779.200 1 3 7 12 125.297 347.237 1 3 8 -9 3268.42 1153.13 1 3 8 -8 1161.10 670.654 1 3 8 -7 2046.66 976.197 1 3 8 -7 581.332 602.051 2 3 8 -6 524.238 562.680 1 3 8 -6 2717.02 1031.12 2 3 8 -5 1127.35 657.024 1 3 8 -4 1321.54 725.018 1 3 8 -3 1011.06 682.803 1 3 8 -2 335.376 299.012 1 3 8 -1 1542.76 688.530 1 3 8 0 2996.34 971.615 1 3 8 1 3604.16 1134.10 1 3 8 2 1840.14 822.744 1 3 8 3-679.536 513.366 1 3 8 4 2862.76 1001.13 1 3 8 5 2234.82 857.620 1 3 8 6 1625.76 809.398 1 3 8 7-51.3131 453.582 1 3 8 8 1523.98 793.180 1 3 8 9 879.691 662.932 1 3 8 10 781.029 657.376 1 3 9 -5 60.0401 505.193 1 3 9 -4 788.604 531.678 1 3 9 -3 502.577 551.227 1 3 9 -2 270.339 379.532 1 3 9 -1 2207.65 897.548 1 3 9 0 289.238 453.497 1 3 9 1 995.600 508.533 1 3 9 2 47.6004 355.090 1 3 9 3-112.656 446.942 1 3 9 4 269.347 463.275 1 3 9 5 628.762 603.131 1 3 9 6 1758.42 969.884 1 3 9 7 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1 -11 8916.25 1271.77 2 4 -1 10 6195.08 1149.08 1 4 -1 9-230.530 264.847 1 4 -1 8 17933.5 1783.38 1 4 -1 7 1329.28 464.572 1 4 1 -6 4832.83 940.140 1 4 -1 6 4684.78 866.938 1 4 -1 5 20414.2 1669.38 1 4 1 -5 21885.5 1880.57 1 4 -1 4 8345.42 1044.58 1 4 1 -4 7171.18 1064.38 1 4 -1 3 10900.0 1130.16 1 4 1 -3 12120.0 1366.11 1 4 -1 2 9591.27 1029.28 1 4 1 -2 10379.2 1260.78 1 4 -1 1 8358.67 952.846 1 4 1 -1 8251.17 1097.79 1 4 1 0 10900.4 1304.42 1 4 -1 0 10710.4 1037.38 1 -4 1 0 12246.4 1109.07 1 4 -1 -1 8307.21 934.219 1 4 1 1 8322.48 1125.69 1 -4 1 -1 9651.48 1020.27 1 4 1 2 12228.4 1370.91 1 -4 1 -2 10257.4 1096.42 1 4 -1 -2 10634.9 1034.92 1 4 1 3 10680.3 1309.43 1 4 -1 -3 10573.8 1064.38 1 4 1 4 8731.81 1209.71 1 4 -1 -4 8522.24 984.615 1 4 1 5 26637.6 2137.45 1 4 -1 -5 24797.4 1674.65 1 4 -1 -6 3662.33 696.387 1 4 1 6 5167.87 985.973 1 4 1 7 2046.51 736.614 1 4 1 8 20372.0 2014.11 1 4 1 9 129.825 485.142 1 4 1 10 5342.67 1158.52 1 4 -1 -10 4739.70 769.280 2 4 -1 -11 8486.10 1019.80 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2 -7 5032.38 1136.25 1 5 -2 6 12651.5 1434.68 1 5 2 -6 11446.3 1649.58 1 5 2 -5 3629.66 925.781 1 5 -2 5 4313.58 828.629 1 5 2 -4 23.7236 256.443 1 5 -2 4 840.906 384.780 1 5 -2 3 10927.0 1186.89 1 5 2 -3 12496.7 1651.97 1 5 -2 2 15968.2 1374.00 1 5 2 -2 16739.0 1880.15 1 5 -2 1 4102.71 690.983 1 5 2 -1 3009.98 861.705 1 5 -2 0 7889.83 920.712 1 5 2 0 8673.24 1348.00 1 5 -2 -1 3599.85 607.627 1 5 2 1 2492.44 751.375 1 5 2 2 15140.9 1835.85 1 5 -2 -2 14852.6 1222.28 1 5 -2 -3 11617.0 1097.29 1 5 2 3 12186.3 1635.60 1 5 2 4 1080.23 628.296 1 5 -2 -4 301.567 276.964 1 5 2 5 3241.44 901.346 1 5 -2 -5 3558.86 647.311 1 5 2 6 16102.6 1949.71 1 5 -2 -6 11884.3 1209.54 1 5 2 7 4775.96 1087.09 1 5 -2 -7 5011.88 819.154 1 5 2 8 5185.12 1170.10 1 5 -2 -8 6614.39 976.340 1 5 -2 -9 244.966 298.942 1 5 2 9 551.249 502.249 1 5 -2 -10 1727.22 542.007 1 5 2 10 3251.45 974.435 1 5 2 11 3708.19 1049.94 1 5 2 12 2099.57 847.596 1 5 2 13 1364.64 760.694 1 5 2 14 2935.53 1068.54 1 5 3 -16 121.273 567.354 2 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783.265 1 5 3 7 385.708 447.163 1 5 3 8 1608.79 697.471 1 5 3 9 6663.05 1411.85 1 5 3 10 6117.76 1389.68 1 5 3 11 2938.53 994.410 1 5 3 12 3286.07 1082.95 1 5 3 13 3333.60 1207.63 1 5 4 -13 1180.70 774.239 2 5 4 -12 2865.40 1079.57 1 5 4 -12 1636.80 850.093 2 5 4 -11 1131.99 765.254 1 5 4 -10 849.047 590.524 1 5 4 -9 871.122 674.448 1 5 4 -8 4454.97 1232.78 1 5 4 -7 8559.85 1642.76 1 5 4 -6 325.138 447.317 1 5 4 -5 1635.55 751.971 1 5 4 -4 5259.27 1254.73 1 5 4 -3 2666.20 896.547 1 5 4 -2 5452.70 1248.06 1 5 4 -1 11556.8 1752.68 1 5 4 0 8766.35 1564.06 1 5 4 1 10825.3 1698.18 1 5 4 2 2902.45 948.935 1 5 4 3 2269.22 887.589 1 5 4 4 6625.29 1384.17 1 5 4 5 2056.64 799.914 1 5 4 6 389.490 353.702 1 5 4 7 6456.22 1432.06 1 5 4 8 4324.06 1175.00 1 5 4 9 1030.45 610.749 1 5 4 10 789.419 600.557 1 5 4 11 452.942 340.744 1 5 4 12 1808.82 890.591 1 5 5 -10 326.431 389.315 1 5 5 -9 1337.58 799.570 1 5 5 -8 3665.52 1156.95 1 5 5 -7 1142.28 785.877 1 5 5 -6 3388.58 1154.79 1 5 5 -5 1642.62 823.985 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1 6 0 -1 182.867 269.157 1 6 0 1 569.930 436.349 1 6 0 2 308.472 422.876 1 6 0 -2 655.511 406.176 1 6 0 3 1784.49 664.974 1 6 0 -3 544.401 470.414 1 6 0 4 8169.12 1338.77 1 6 0 -4 7949.86 1304.77 1 6 0 5 6862.20 1254.64 1 6 0 -5 5455.35 1085.25 1 6 0 6 322.330 414.680 1 6 0 -6 519.416 341.927 1 6 0 -7 651.753 537.029 1 6 0 7-51.7907 253.358 1 6 0 -8 540.907 416.606 1 6 0 8 176.245 318.301 1 6 0 -9 1073.23 562.309 1 6 0 9 2019.85 727.931 1 6 0 -10 2499.64 884.266 1 6 0 10 3225.95 986.171 1 6 0 11 619.813 553.565 1 6 0 -11 236.602 430.132 1 6 0 12 6.17038 507.224 1 6 0 -12 1171.96 724.687 1 6 0 13 1004.50 730.641 1 6 1 -14 127.204 378.064 1 6 -1 14 807.996 657.746 1 6 -1 13 269.487 505.560 1 6 1 -13 731.673 547.918 1 6 -1 12 1004.24 550.075 1 6 1 -12 766.887 481.819 1 6 -1 11 636.621 433.877 1 6 1 -11 534.793 475.301 1 6 -1 10 1683.22 750.746 1 6 1 -10 2552.16 938.617 1 6 -1 9-65.6562 268.507 1 6 1 -9 1858.54 797.431 1 6 1 -8 738.263 473.253 1 6 -1 8 1747.55 735.333 1 6 1 -7 1228.96 593.058 1 6 -1 7 1638.95 630.384 1 6 1 -6 4364.69 1034.26 1 6 -1 6 4912.89 1040.92 1 6 -1 5 692.434 455.816 1 6 1 -5 673.669 411.614 1 6 -1 4 1220.06 546.713 1 6 1 -4 1023.44 522.369 1 6 1 -3 12028.9 1675.89 1 6 -1 3 9544.00 1318.94 1 6 -1 2 11031.0 1387.16 1 6 1 -2 9989.74 1516.29 1 6 -1 1 9900.98 1352.30 1 6 1 -1 7541.63 1310.52 1 6 1 0 31285.2 2647.30 1 6 -1 0 34295.2 2394.23 1 6 1 1 7310.09 1301.81 1 6 -1 -1 7539.05 1152.69 1 6 -1 -2 8494.52 1204.65 1 6 1 2 9851.68 1506.88 1 6 1 3 8754.23 1434.14 1 6 -1 -3 9047.93 1222.74 1 6 1 4 817.587 496.685 1 6 -1 -4 618.277 351.522 1 6 1 5 684.411 559.922 1 6 -1 -5 302.078 361.019 1 6 1 6 4585.89 1088.34 1 6 -1 -6 3903.46 852.076 1 6 1 7 2558.04 896.272 1 6 -1 -7 1299.37 569.971 1 6 1 8 762.964 518.715 1 6 -1 -8 551.721 358.267 1 6 1 9 1694.66 878.579 1 6 1 10 992.787 552.007 1 6 1 11 1085.58 695.944 1 6 1 12 1511.99 843.788 1 6 -2 14 1285.62 696.908 1 6 2 -13 2105.18 956.725 1 6 -2 13 640.553 560.008 1 6 2 -13 701.602 512.992 2 6 2 -12 562.350 553.663 1 6 -2 12 731.597 588.287 1 6 -2 11 1611.16 744.626 1 6 2 -11 1743.94 836.196 1 6 -2 10 701.372 546.742 1 6 2 -10 307.960 403.315 1 6 -2 9 2601.07 833.550 1 6 2 -9 1389.90 773.342 1 6 -2 8 1955.23 731.709 1 6 2 -8 1715.29 777.397 1 6 -2 7 535.439 447.055 1 6 2 -7 474.983 525.657 1 6 -2 6 2874.70 787.987 1 6 2 -6 5893.10 1338.54 1 6 2 -5 2258.91 768.736 1 6 -2 5 4480.55 913.553 1 6 2 -4 2866.61 912.409 1 6 -2 4 1609.19 572.010 1 6 -2 3 3735.76 804.697 1 6 2 -3 4526.66 1102.42 1 6 -2 2 2907.13 678.562 1 6 2 -2 3201.27 937.516 1 6 2 -1 14597.9 1911.85 1 6 -2 1 17237.4 1562.45 1 6 -2 0 2108.35 572.703 1 6 2 0 1350.13 657.679 1 6 2 1 14598.2 1939.16 1 6 2 2 3085.01 917.813 1 6 2 3 5824.55 1254.89 1 6 2 4 768.298 546.983 1 6 2 5 4104.32 1107.39 1 6 2 6 1899.69 820.092 1 6 2 7 1261.01 710.112 1 6 2 8 976.194 634.068 1 6 2 9 1339.49 781.005 1 6 2 10 1601.93 739.471 1 6 2 11 1981.21 895.447 1 6 3 -13 2551.08 964.157 2 6 3 -11 1369.60 750.224 1 6 3 -10 803.281 670.383 1 6 3 -9 1479.49 780.493 1 6 3 -8 6317.29 1446.93 1 6 3 -7 2818.64 1021.32 1 6 3 -6 1869.52 809.419 1 6 3 -5 274.115 541.085 1 6 3 -4 8128.21 1551.93 1 6 3 -3 1372.49 669.062 1 6 3 -2 2193.22 858.527 1 6 3 -1 3319.87 1000.32 1 6 3 0 3294.69 979.960 1 6 3 1 3450.38 982.190 1 6 3 2 1489.65 684.106 1 6 3 3-126.536 429.272 1 6 3 4 6626.68 1394.17 1 6 3 5 536.502 616.730 1 6 3 6 1370.85 672.755 1 6 3 7 1056.79 674.943 1 6 3 8 4277.63 1245.25 1 6 3 9 1278.91 759.433 1 6 3 10 1179.77 728.045 1 6 4 -9 1692.50 876.796 1 6 4 -8 2712.91 1067.29 1 6 4 -7 2880.85 1131.90 1 6 4 -6 2321.18 954.690 1 6 4 -5 4207.70 1214.50 1 6 4 -4 1260.05 736.093 1 6 4 -3 258.329 602.102 1 6 4 -2 4254.18 1144.68 1 6 4 -1 1415.66 714.495 1 6 4 0 1108.80 644.296 1 6 4 1 1516.21 769.454 1 6 4 2 4162.99 1170.28 1 6 4 3 974.279 731.792 1 6 4 4 2823.81 1018.16 1 6 4 5 4712.96 1290.56 1 6 4 6 3520.72 1131.53 1 6 4 7 1761.86 915.407 1 6 4 8 2836.80 1009.66 1 6 4 9 5058.82 1426.77 1 6 5 -6 1551.38 885.553 1 6 5 -5 2191.60 987.357 1 6 5 -4 696.530 632.497 1 6 5 -3 2628.60 1025.19 1 6 5 -2 1627.18 794.679 1 6 5 -1 999.710 716.187 1 6 5 0 996.519 688.358 1 6 5 1 52.9092 314.250 1 6 5 2 1742.47 766.590 1 6 5 3 3035.14 1119.15 1 6 5 4 1726.37 892.346 1 6 5 5 586.533 515.039 1 6 5 6 373.229 530.492 1 7 0 0 519.909 396.879 1 7 0 -1 2749.70 860.678 1 7 0 1 1861.31 744.100 1 7 0 -2 6236.84 1241.94 1 7 0 2 5006.39 1117.55 1 7 0 -3 1047.34 595.944 1 7 0 3 33.5451 316.644 1 7 0 4 2088.33 785.874 1 7 0 -4 1934.07 684.985 1 7 0 5 978.646 530.849 1 7 0 6 3774.15 1025.63 1 7 0 7 349.009 319.872 1 7 0 8 889.942 643.762 1 7 0 9 307.447 381.156 1 7 0 10 3006.01 1030.52 1 7 1 -9 622.566 558.557 1 7 -1 8 315.435 254.580 1 7 1 -8 196.099 465.358 1 7 1 -7 1119.21 652.101 1 7 -1 7 1011.82 594.115 1 7 1 -6 1453.42 729.992 1 7 1 -5 2961.75 919.628 1 7 1 -4 4713.70 1161.81 1 7 1 -3-127.286 226.767 1 7 1 -2-266.111 288.600 1 7 1 -1 3581.06 971.538 1 7 1 0 2252.51 790.597 1 7 1 1 3493.34 966.447 1 7 1 2 993.551 642.048 1 7 1 3 999.799 638.072 1 7 1 4 2131.54 872.467 1 7 1 5 3696.60 1064.02 1 7 1 6 363.695 479.200 1 7 1 7 986.675 700.680 1 7 1 8 1432.06 818.427 1 7 1 9 1409.02 830.948 1 7 2 -10 1311.86 822.136 1 7 2 -9-84.6641 405.442 1 7 2 -8 1701.38 870.671 1 7 2 -7 734.936 575.815 1 7 2 -6 2070.92 843.994 1 7 2 -5 1485.29 758.959 1 7 2 -4 750.369 469.728 1 7 2 -3 8923.02 1637.70 1 7 2 -2 428.554 409.644 1 7 2 -1 957.622 604.717 1 7 2 0 4543.25 1231.11 1 7 2 1 2034.30 737.891 1 7 2 2 2293.46 939.776 1 7 2 3 9814.89 1728.31 1 7 2 4 1268.05 739.315 1 7 2 5 666.317 491.159 1 7 2 6 1442.84 788.612 1 7 2 7 1798.98 838.086 1 7 2 8 1635.18 779.514 1 7 3 -7 534.579 676.824 1 7 3 -6 1987.97 910.620 1 7 3 -5 1209.08 863.641 1 7 3 -4 427.400 585.120 1 7 3 -3 224.614 274.888 1 7 3 -2 2773.06 974.141 1 7 3 -1 1935.10 854.580 1 7 3 0 1537.27 821.699 1 7 3 1 1917.37 924.428 1 7 3 2 1849.47 891.220 1 7 3 3 840.709 556.107 1 7 3 4 1433.36 818.927 1 7 3 5 1741.45 927.204 1 7 3 6 2341.38 976.411 1 7 4 -3 210.910 365.834 1 7 4 -2 261.304 631.455 1 7 4 -1 1273.04 743.862 1 7 4 0 986.152 683.587 1 7 4 1 1225.92 757.552 1 7 4 2 278.765 424.424 1 8 1 2-43.1311 292.061 1 8 1 3-103.704 441.859 1 8 1 4 2007.26 853.573 1 8 1 5 1869.68 901.837 1 8 2 -3 655.651 517.893 1 8 2 -2 1346.77 779.258 1 8 2 -1-48.0195 558.129 1 8 2 0 2470.21 986.191 1 8 2 1 2711.06 1019.32 1 0 0 0 0.00 0.00 0 TITL shI_3390_RoLa in P2(1)2(1)2(1) REM P2(1)2(1)2(1) (#19 in standard setting) CELL 0.71073 6.035565 7.650091 15.785074 90.0000 90.0000 90.0000 ZERR 2.00 0.000469 0.000636 0.001357 0.0000 0.0000 0.0000 LATT -1 SYMM -x+1/2,-y, z+1/2 SYMM -x, y+1/2,-z+1/2 SYMM x+1/2,-y+1/2,-z SFAC C H N O UNIT 40.00 40.00 8.00 8.00 TREF HKLF 4 END ; _shelx_hkl_checksum 54699 _shelx_res_file ; TITL shi_3390_rola_a.res in P2(1)2(1)2(1) shi_3390_rola.res created by SHELXL-2018/3 at 14:48:35 on 19-Dec-2023 REM Old TITL shI_3390_RoLa in P212121 #19 REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.181, Rweak 0.198, Alpha 0.004, Orientation as input REM Flack x = -1.293 ( 1.415 ) from Parsons' quotients REM Formula found by SHELXT: C1 N O1 CELL 0.71073 6.035565 7.650091 15.785074 90 90 90 ZERR 4 0.000469 0.000636 0.001357 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N O UNIT 16 40 16 8 ISOR 0.01 0.02 N3 L.S. 10 PLAN 1 CONF BOND $H MORE -1 fmap 2 acta 52 SHEL 99 0.84 OMIT 2 5 13 REM REM REM WGHT 0.031100 FVAR 11.78986 O1 4 -0.349513 -0.660060 -0.391584 11.00000 0.06398 0.04268 = 0.05362 -0.00617 -0.00384 0.01818 O2 4 -0.105338 -0.305676 -0.380633 11.00000 0.03175 0.08359 = 0.05418 0.01025 0.00537 -0.01064 N1 3 -0.571549 -0.438910 -0.434095 11.00000 0.03456 0.03864 = 0.03353 -0.00642 -0.00675 0.00294 N2 3 -0.626463 -0.261683 -0.420585 11.00000 0.03213 0.03725 = 0.04757 0.00105 0.00109 0.00256 N3 3 -0.283094 -0.372332 -0.259210 11.00000 0.03615 0.05142 = 0.03773 -0.00149 -0.00458 -0.00374 N4 3 -0.475784 -0.450763 -0.225224 11.00000 0.05780 0.05639 = 0.03883 -0.00189 0.00525 -0.00196 C1 1 -0.705556 -0.545280 -0.491300 11.00000 0.05979 0.05541 = 0.04079 -0.01134 -0.01341 -0.00464 AFIX 3 H1A 2 -0.703336 -0.494920 -0.546990 11.00000 -1.50000 H1B 2 -0.855356 -0.549500 -0.470930 11.00000 -1.50000 H1C 2 -0.646056 -0.661570 -0.493510 11.00000 -1.50000 AFIX 0 C2 1 -0.403968 -0.505008 -0.389632 11.00000 0.03709 0.04325 = 0.02670 -0.00230 0.00718 0.00583 C3 1 -0.257052 -0.378690 -0.342106 11.00000 0.02881 0.04435 = 0.03451 0.00477 -0.00215 0.00805 C4 1 -0.128285 -0.279335 -0.204269 11.00000 0.05706 0.08446 = 0.05666 -0.01531 -0.01716 -0.00794 AFIX 3 H4C 2 -0.188175 -0.166675 -0.190369 11.00000 -1.50000 H4D 2 0.010785 -0.264855 -0.232939 11.00000 -1.50000 H4E 2 -0.105945 -0.345315 -0.153239 11.00000 -1.50000 AFIX 0 H2A 2 -0.762827 -0.254588 -0.404072 11.00000 0.06133 H4A 2 -0.537434 -0.378261 -0.198648 11.00000 0.05299 H2B 2 -0.621399 -0.207788 -0.470712 11.00000 0.05604 H4B 2 -0.432000 -0.547762 -0.186812 11.00000 0.12084 HKLF 4 REM shi_3390_rola_a.res in P2(1)2(1)2(1) REM wR2 = 0.0932, GooF = S = 1.038, Restrained GooF = 1.036 for all data REM R1 = 0.0497 for 1014 Fo > 4sig(Fo) and 0.0680 for all 1279 data REM 107 parameters refined using 6 restraints END WGHT 0.0313 0.0000 REM Highest difference peak 0.142, deepest hole -0.115, 1-sigma level 0.034 Q1 1 -0.8180 -0.4274 -0.5171 11.00000 0.05 0.14 ; _shelx_res_checksum 67873 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O O1 -0.3495(5) -0.6601(3) -0.39158(16) 0.0534(8) Uani d 1 . . O O2 -0.1053(4) -0.3057(4) -0.38063(17) 0.0565(8) Uani d 1 . . N N1 -0.5715(5) -0.4389(3) -0.43410(17) 0.0356(8) Uani d 1 . . N N2 -0.6265(6) -0.2617(4) -0.4206(2) 0.0390(8) Uani d 1 . . N N3 -0.2831(5) -0.3723(4) -0.2592(2) 0.0418(8) Uani d 1 . . N N4 -0.4758(7) -0.4508(6) -0.2252(2) 0.0510(10) Uani d 1 . . C C1 -0.7056(7) -0.5453(5) -0.4913(2) 0.0520(11) Uani d 1 . . H H1A -0.703336 -0.494920 -0.546990 0.078 Uiso d 1 . . H H1B -0.855356 -0.549500 -0.470930 0.078 Uiso d 1 . . H H1C -0.646056 -0.661570 -0.493510 0.078 Uiso d 1 . . C C2 -0.4040(6) -0.5050(5) -0.3896(2) 0.0357(9) Uani d 1 . . C C3 -0.2571(6) -0.3787(4) -0.3421(2) 0.0359(9) Uani d 1 . . C C4 -0.1283(7) -0.2793(5) -0.2043(3) 0.0661(13) Uani d 1 . . H H4C -0.188175 -0.166675 -0.190369 0.099 Uiso d 1 . . H H4D 0.010785 -0.264855 -0.232939 0.099 Uiso d 1 . . H H4E -0.105945 -0.345315 -0.153239 0.099 Uiso d 1 . . H H2A -0.763(8) -0.255(5) -0.404(2) 0.061(14) Uiso d 1 . . H H4A -0.537(7) -0.378(5) -0.199(2) 0.053(15) Uiso d 1 . . H H2B -0.621(6) -0.208(5) -0.471(2) 0.056(14) Uiso d 1 . . H H4B -0.432(9) -0.548(7) -0.187(3) 0.12(2) 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 0.0640(19) 0.0427(15) 0.0536(18) 0.0182(15) -0.0038(16) -0.0062(13) O2 0.0318(15) 0.084(2) 0.0542(18) -0.0106(15) 0.0054(15) 0.0102(15) N1 0.0346(17) 0.0386(16) 0.0335(17) 0.0029(15) -0.0068(15) -0.0064(14) N2 0.0321(19) 0.0372(18) 0.048(2) 0.0026(17) 0.0011(18) 0.0011(17) N3 0.0361(18) 0.051(2) 0.0377(19) -0.0037(18) -0.0046(16) -0.0015(15) N4 0.058(3) 0.056(2) 0.039(2) -0.002(2) 0.0052(19) -0.002(2) C1 0.060(3) 0.055(2) 0.041(2) -0.005(2) -0.013(2) -0.011(2) C2 0.037(2) 0.043(2) 0.0267(19) 0.0058(19) 0.0072(19) -0.0023(17) C3 0.029(2) 0.044(2) 0.035(2) 0.0081(19) -0.0022(18) 0.0048(18) C4 0.057(3) 0.084(3) 0.057(3) -0.008(3) -0.017(3) -0.015(3) 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N2 N1 C1 . . 119.9(3) yes C2 N1 N2 . . 117.6(3) yes C2 N1 C1 . . 122.4(3) yes N1 N2 H2A . . 109(3) no N1 N2 H2B . . 108(2) no H2A N2 H2B . . 106(4) no N4 N3 C4 . . 120.5(3) yes C3 N3 N4 . . 117.3(3) yes C3 N3 C4 . . 122.1(4) yes N3 N4 H4A . . 107(3) no N3 N4 H4B . . 109(3) no H4A N4 H4B . . 109(4) no N1 C1 H1A . . 109.6 no N1 C1 H1B . . 109.5 no N1 C1 H1C . . 109.4 no H1A C1 H1B . . 109.5 no H1A C1 H1C . . 109.5 no H1B C1 H1C . . 109.5 no O1 C2 N1 . . 123.8(3) yes O1 C2 C3 . . 118.2(3) yes N1 C2 C3 . . 117.7(3) yes O2 C3 N3 . . 124.1(4) yes O2 C3 C2 . . 118.7(3) yes N3 C3 C2 . . 116.5(3) yes N3 C4 H4C . . 109.4 no N3 C4 H4D . . 109.6 no N3 C4 H4E . . 109.4 no H4C C4 H4D . . 109.5 no H4C C4 H4E . . 109.5 no H4D C4 H4E . . 109.5 no 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 C2 . 1.231(4) yes O2 C3 . 1.233(4) yes N1 N2 . 1.412(4) yes N1 C1 . 1.460(4) yes N1 C2 . 1.331(4) yes N2 H2A . 0.87(4) no N2 H2B . 0.89(4) no N3 N4 . 1.414(4) yes N3 C3 . 1.319(4) yes N3 C4 . 1.460(4) yes N4 H4A . 0.79(4) no N4 H4B . 0.99(5) no C1 H1A . 0.9599 no C1 H1B . 0.9601 no C1 H1C . 0.9600 no C2 C3 . 1.511(5) yes C4 H4C . 0.9600 no C4 H4D . 0.9600 no C4 H4E . 0.9601 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C1 H1C O1 ? ? 4_434 0.96 2.58 3.042(4) 110 yes N2 H2A O2 . . 1_455 0.87(5) 2.13(5) 2.977(4) 164(4) yes N2 H2B O2 . . 4_444 0.90(3) 2.35(3) 3.182(4) 155(3) yes N4 H4A O1 . . 3_454 0.79(4) 2.30(4) 3.075(5) 169(4) yes N4 H4B N2 . . 3_444 0.99(5) 2.38(5) 3.367(5) 170(4) yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O1 C2 C3 O2 . . . . 89.9(4) ? O1 C2 C3 N3 . . . . -81.4(4) ? N1 C2 C3 O2 . . . . -83.2(4) ? N1 C2 C3 N3 . . . . 105.5(4) ? N2 N1 C2 O1 . . . . 175.1(4) ? N2 N1 C2 C3 . . . . -12.2(4) ? N4 N3 C3 O2 . . . . 174.8(4) ? N4 N3 C3 C2 . . . . -14.4(5) ? C1 N1 C2 O1 . . . . -1.2(5) ? C1 N1 C2 C3 . . . . 171.6(3) ? C4 N3 C3 O2 . . . . -1.4(6) ? C4 N3 C3 C2 . . . . 169.4(3) ?