#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/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/μ'
_diffrn_measurement_method       ω
_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/[σ²(Fₒ)+0.001Fₒ²]'
_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
