#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/51/2005182.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_2005182 loop_ _publ_author_name 'Singh, P.' 'Izydore, R. A.' _publ_section_title ; 1,2-Diacetyl-4-phenyl-1,2,4-triazolidine-3,5-dione ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1817 _journal_page_last 1820 _journal_paper_doi 10.1107/S0108270196000947 _journal_volume 52 _journal_year 1996 _chemical_formula_sum 'C12 H11 N3 O4' _chemical_formula_weight 261.24 _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_type_scat_source IntTabIV _cell_angle_alpha 103.94(3) _cell_angle_beta 92.10(3) _cell_angle_gamma 97.31(3) _cell_formula_units_Z 6 _cell_length_a 11.002(4) _cell_length_b 12.962(5) _cell_length_c 13.643(6) _cell_measurement_reflns_used 25 _cell_measurement_temperature 298 _cell_measurement_theta_max 13.5 _cell_measurement_theta_min 10 _cell_volume 1868.4(13) _diffrn_measurement_device 'Siemens R3m/\m' _diffrn_measurement_method \w _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.023 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 10540 _diffrn_reflns_theta_max 29 _diffrn_standards_decay_% 2.3 _diffrn_standards_interval_time 48 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.08 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.39 _exptl_crystal_description 'thin plate' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.34 _refine_diff_density_min -0.29 _refine_ls_extinction_coef 1.3E-6(4) _refine_ls_extinction_method Zachariasen _refine_ls_goodness_of_fit_obs 1.3 _refine_ls_hydrogen_treatment refall _refine_ls_number_parameters 647 _refine_ls_number_reflns 4346 _refine_ls_R_factor_obs 0.067 _refine_ls_shift/esd_max 0.49 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/[\s^2^(F~o~)+0.001F~o~^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.078 _reflns_number_observed 4346 _reflns_number_total 9947 _reflns_observed_criterion I>=2.5\s(I) _cod_data_source_file sz1002.cif _cod_data_source_block sz1002a _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value '1/[\s^2^(F~o~)+0.001F~o~^2^]' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(F~o~)+0.001F~o~^2^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 1868.0(10) _cod_database_code 2005182 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv N(1A) .2870(3) .8311(2) .4740(2) .0290(10) N(2A) .2896(3) .7204(2) .4309(2) .0290(10) C(1A) .1690(3) .6668(3) .4188(3) .0310(10) O(1A) .1364(3) .5727(2) .3863(2) .0420(10) N(3A) .0954(3) .7457(3) .4519(2) .0330(10) C(2A) .1625(4) .8461(3) .4871(3) .0330(10) O(2A) .1252(3) .9287(3) .5230(3) .0500(10) C(3A) .3837(4) .8852(3) .5470(3) .0330(10) O(3A) .4655(3) .8380(3) .5642(2) .0430(10) C(4A) .3776(5) 1.0003(4) .5955(4) .054(2) C(5A) .3811(3) .6979(3) .3603(3) .0350(10) O(4A) .4548(3) .7684(3) .3496(2) .0460(10) C(6A) .3775(5) .5817(4) .3091(4) .060(2) C(7A) -.0354(3) .7247(3) .4599(3) .0350(10) C(8A) -0.1142(4) .7633(4) .4024(4) .050(2) C(9A) -0.2390(4) .7455(5) .4148(4) .062(2) C(10A) -0.2818(4) .6913(4) .4840(4) .058(2) C(11A) -0.2024(4) .6529(4) .5414(4) .055(2) C(12A) -.0771(4) .6687(4) .5293(4) .043(2) N(1B) .5961(3) .2434(3) .2475(2) .0310(10) N(2B) .6002(3) .1342(3) .2015(3) .0330(10) C(1B) .4787(4) .0794(3) .1872(3) .0370(10) O(1B) .4479(3) -.0132(3) .1487(3) .0610(10) N(3B) .4062(3) .1560(3) .2258(3) .0320(10) C(2B) .4724(4) .2562(3) .2653(3) .0340(10) O(2B) .4345(3) .3362(2) .3062(3) .0480(10) C(3B) .6965(4) .2958(3) .3193(3) .0350(10) O(3B) .7768(3) .2469(3) .3354(2) .0450(10) C(4B) .6921(5) .4111(4) .3673(4) .051(2) C(5B) .6954(4) .1122(4) .1340(3) .0390(10) O(4B) .7661(3) .1842(3) .1214(2) .0520(10) C(6B) .6999(5) -.0039(4) .0876(5) .070(2) C(7B) .2759(3) .1310(3) .2366(3) .0310(10) C(8B) .2395(4) .0862(4) .3137(3) .0390(10) C(9B) .1143(4) .0644(4) .3263(4) .049(2) C(10B) .0304(4) .0894(4) .2611(4) .051(2) C(11B) .0694(4) .1339(4) .1842(4) .054(2) C(12B) .1927(4) .1554(4) .1706(3) .043(2) N(1C) -.0427(3) .5928(3) .1549(2) .0310(10) N(2C) -.0010(3) .6789(3) .1129(2) .0310(10) C(1C) -0.1038(3) .7194(3) .0790(3) .0310(10) O(1C) -0.1036(3) .7929(3) .0414(3) .0520(10) N(3C) -0.2040(3) .6557(3) .1009(2) .0310(10) C(2C) -0.1726(3) .5762(3) .1447(3) .0340(10) O(2C) -0.2396(3) .5089(3) .1686(3) .0520(10) C(3C) .0282(4) .5058(3) .1361(3) .0380(10) O(3C) .1177(3) .5129(3) .0901(3) .0560(10) C(4C) -.0151(6) .4157(4) .1823(6) .061(2) C(5C) .1110(3) .7451(3) .1589(3) .0310(10) O(4C) .1629(3) .7239(3) .2272(2) .0500(10) C(6C) .1538(4) .8344(4) .1120(4) .042(2) C(7C) -0.3289(3) .6615(3) .0668(3) .0310(10) C(8C) -0.4039(4) .7145(4) .1334(4) .051(2) C(9C) -0.5222(4) .7203(4) .0984(4) .058(2) C(10C) -0.5632(4) .6719(4) .0003(4) .049(2) C(11C) -0.4873(4) .6197(4) -.0647(4) .052(2) C(12C) -0.3681(4) .6145(4) -.0316(3) .047(2) H(4AA) .312(4) 1.004(3) .630(3) .046(12) H(4AB) .353(4) 1.037(4) .548(3) .051(13) H(4AC) .448(6) 1.032(5) .625(5) .09(2) H(6AA) .297(7) .547(6) .283(6) .15(3) H(6AB) .387(5) .543(4) .358(4) .087(18) H(6AC) .444(4) .574(4) .274(4) .045(13) H(8A) -.080(4) .804(3) .358(3) .037(12) H(9A) -0.295(5) .774(4) .377(4) .065(15) H(10A) -0.369(5) .684(5) .503(4) .083(18) H(11A) -0.229(5) .622(5) .590(5) .10(2) H(12A) -.021(4) .646(3) .575(3) .036(11) H(4BA) .679(3) .448(3) .323(3) .031(10) H(4BB) .630(5) .420(4) .419(4) .070(16) H(4BC) .772(5) .442(4) .401(4) .079(17) H(6BA) .709(7) -.032(6) .131(6) .16(3) H(6BB) .762(5) -.005(5) .049(5) .10(2) H(6BC) .622(5) -.037(5) .064(5) .096(19) H(8B) .303(4) .066(4) .358(4) .060(15) H(9B) .093(5) .032(4) .385(4) .069(16) H(10B) -.051(4) .076(4) .282(4) .059(15) H(11B) .017(4) .142(3) .139(3) .043(12) H(12B) .219(4) .187(4) .115(3) .051(13) H(4CA) -.037(7) .442(6) .246(6) .10(3) H(4CB) .035(5) .368(5) .165(4) .067(17) H(4CC) -.088(5) .376(5) .150(4) .075(18) H(6CA) .150(4) .807(4) .043(4) .053(15) H(6CB) .102(5) .892(4) .132(4) .075(16) H(6CC) .235(4) .864(3) .140(3) .039(12) H(8C) -0.374(5) .750(4) .199(4) .082(18) H(9C) -0.580(5) .753(4) .138(4) .073(17) H(10C) -0.640(4) .674(4) -.020(4) .058(15) H(11C) -0.512(4) .588(4) -0.130(3) .044(13) H(12C) -0.314(4) .577(3) -.072(3) .037(11) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag N(2A) N(1A) C(2A) 107.8(3) yes C(2A) N(1A) C(3A) 122.5(3) yes N(1A) N(2A) C(5A) 114.7(3) yes N(2A) C(1A) O(1A) 127.2(4) yes O(1A) C(1A) N(3A) 127.2(3) yes C(1A) N(3A) C(7A) 124.2(3) yes N(1A) C(2A) N(3A) 105.5(3) yes N(3A) C(2A) O(2A) 127.8(4) yes N(1A) C(3A) C(4A) 116.6(4) yes N(2A) C(5A) O(4A) 119.8(4) yes O(4A) C(5A) C(6A) 125.5(4) yes N(3A) C(7A) C(12A) 118.3(4) yes C(7A) C(8A) C(9A) 118.6(5) yes C(9A) C(10A) C(11A) 120.7(5) yes C(7A) C(12A) C(11A) 118.8(5) yes N(2B) N(1B) C(3B) 115.5(3) yes N(1B) N(2B) C(1B) 108.3(3) yes C(1B) N(2B) C(5B) 125.6(3) yes N(2B) C(1B) N(3B) 105.3(3) yes C(1B) N(3B) C(2B) 113.1(3) yes C(2B) N(3B) C(7B) 123.3(3) yes N(1B) C(2B) O(2B) 127.0(3) yes N(1B) C(3B) O(3B) 119.7(3) yes O(3B) C(3B) C(4B) 125.0(4) yes N(2B) C(5B) C(6B) 115.4(4) yes N(3B) C(7B) C(8B) 118.8(4) yes C(8B) C(7B) C(12B) 122.0(4) yes C(8B) C(9B) C(10B) 119.1(5) yes C(10B) C(11B) C(12B) 121.0(5) yes N(2C) N(1C) C(2C) 108.1(3) yes C(2C) N(1C) C(3C) 122.3(3) yes N(1C) N(2C) C(5C) 116.5(3) yes N(2C) C(1C) O(1C) 127.6(3) yes O(1C) C(1C) N(3C) 127.7(4) yes C(1C) N(3C) C(7C) 122.7(4) yes N(1C) C(2C) N(3C) 105.0(3) yes N(3C) C(2C) O(2C) 127.6(4) yes N(1C) C(3C) C(4C) 115.2(4) yes N(2C) C(5C) O(4C) 119.2(4) yes O(4C) C(5C) C(6C) 125.4(4) yes N(3C) C(7C) C(12C) 118.7(3) yes C(7C) C(8C) C(9C) 118.4(4) yes C(9C) C(10C) C(11C) 120.3(4) yes C(7C) C(12C) C(11C) 119.0(4) yes N(2A) N(1A) C(3A) 116.7(3) yes N(1A) N(2A) C(1A) 108.6(3) yes C(1A) N(2A) C(5A) 125.0(3) yes N(2A) C(1A) N(3A) 105.6(3) yes C(1A) N(3A) C(2A) 112.5(3) yes C(2A) N(3A) C(7A) 122.9(3) yes N(1A) C(2A) O(2A) 126.7(3) yes N(1A) C(3A) O(3A) 119.3(3) yes O(3A) C(3A) C(4A) 124.2(4) yes N(2A) C(5A) C(6A) 114.6(4) yes N(3A) C(7A) C(8A) 119.9(4) yes C(8A) C(7A) C(12A) 121.7(4) yes C(8A) C(9A) C(10A) 120.5(5) yes C(10A) C(11A) C(12A) 119.8(5) yes N(2B) N(1B) C(2B) 108.0(3) yes C(2B) N(1B) C(3B) 122.9(3) yes N(1B) N(2B) C(5B) 116.2(3) yes N(2B) C(1B) O(1B) 126.5(4) yes O(1B) C(1B) N(3B) 128.2(4) yes C(1B) N(3B) C(7B) 123.1(3) yes N(1B) C(2B) N(3B) 105.3(3) yes N(3B) C(2B) O(2B) 127.7(4) yes N(1B) C(3B) C(4B) 115.3(4) yes N(2B) C(5B) O(4B) 119.6(4) yes O(4B) C(5B) C(6B) 125.0(4) yes N(3B) C(7B) C(12B) 119.2(4) yes C(7B) C(8B) C(9B) 119.2(4) yes C(9B) C(10B) C(11B) 120.5(4) yes C(7B) C(12B) C(11B) 118.2(5) yes N(2C) N(1C) C(3C) 115.4(3) yes N(1C) N(2C) C(1C) 108.9(3) yes C(1C) N(2C) C(5C) 123.7(3) yes N(2C) C(1C) N(3C) 104.7(3) yes C(1C) N(3C) C(2C) 113.3(3) yes C(2C) N(3C) C(7C) 123.4(3) yes N(1C) C(2C) O(2C) 127.5(4) yes N(1C) C(3C) O(3C) 118.7(4) yes O(3C) C(3C) C(4C) 126.0(5) yes N(2C) C(5C) C(6C) 115.3(4) yes N(3C) C(7C) C(8C) 119.6(3) yes C(8C) C(7C) C(12C) 121.7(4) yes C(8C) C(9C) C(10C) 120.4(5) yes C(10C) C(11C) C(12C) 120.2(4) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N(1A) N(2A) 1.418(4) yes N(1A) C(3A) 1.418(4) yes N(2A) C(5A) 1.428(5) yes C(1A) N(3A) 1.386(5) yes N(3A) C(7A) 1.444(5) yes C(3A) O(3A) 1.197(5) yes C(5A) O(4A) 1.182(5) yes C(7A) C(8A) 1.366(7) yes C(8A) C(9A) 1.387(7) yes C(10A) C(11A) 1.369(8) yes N(1B) N(2B) 1.411(4) yes N(1B) C(3B) 1.432(5) yes N(2B) C(5B) 1.430(5) yes C(1B) N(3B) 1.371(5) yes N(3B) C(7B) 1.450(5) yes C(3B) O(3B) 1.193(6) yes C(5B) O(4B) 1.187(6) yes C(7B) C(8B) 1.368(6) yes C(8B) C(9B) 1.395(6) yes C(10B) C(11B) 1.372(8) yes N(1C) N(2C) 1.407(5) yes N(1C) C(3C) 1.430(5) yes N(2C) C(5C) 1.437(4) yes C(1C) N(3C) 1.378(5) yes N(3C) C(7C) 1.451(5) yes C(3C) O(3C) 1.192(5) yes C(5C) O(4C) 1.180(5) yes C(7C) C(8C) 1.369(6) yes C(8C) C(9C) 1.387(7) yes C(10C) C(11C) 1.359(7) yes N(1A) C(2A) 1.419(5) yes N(2A) C(1A) 1.401(5) yes C(1A) O(1A) 1.195(5) yes N(3A) C(2A) 1.378(5) yes C(2A) O(2A) 1.195(5) yes C(3A) C(4A) 1.490(6) yes C(5A) C(6A) 1.494(6) yes C(7A) C(12A) 1.383(7) yes C(9A) C(10A) 1.369(9) yes C(11A) C(12A) 1.389(6) yes N(1B) C(2B) 1.414(5) yes N(2B) C(1B) 1.415(5) yes C(1B) O(1B) 1.188(5) yes N(3B) C(2B) 1.378(5) yes C(2B) O(2B) 1.187(5) yes C(3B) C(4B) 1.487(6) yes C(5B) C(6B) 1.494(7) yes C(7B) C(12B) 1.377(6) yes C(9B) C(10B) 1.380(7) yes C(11B) C(12B) 1.378(6) yes N(1C) C(2C) 1.414(5) yes N(2C) C(1C) 1.414(5) yes C(1C) O(1C) 1.185(6) yes N(3C) C(2C) 1.383(6) yes C(2C) O(2C) 1.185(5) yes C(3C) C(4C) 1.491(9) yes C(5C) C(6C) 1.487(7) yes C(7C) C(12C) 1.362(6) yes C(9C) C(10C) 1.367(7) yes C(11C) C(12C) 1.387(7) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139055054