#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/64/2206496.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_2206496
loop_
_publ_author_name
'Joussef, Antonio C.'
'Silva, Liuz Everson da'
'Bortoluzzi, Adailton J.'
'Foro, Sabine'
_publ_section_title
;2,2-Dimethyl-5-(4H-1,2,4-triazol-4-ylaminomethylene)-1,3-dioxane-4,6-dione
 monohydrate
;
_journal_coeditor_code           NC6036
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2642
_journal_page_last               o2643
_journal_paper_doi               10.1107/S1600536805022750
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C9 H10 N4 O4, H2 O'
_chemical_formula_moiety         'C9 H10 N4 O4, H2 O'
_chemical_formula_sum            'C9 H12 N4 O5'
_chemical_formula_weight         256.23
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.786(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.012(5)
_cell_length_b                   5.356(5)
_cell_length_c                   12.937(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      20.36
_cell_measurement_theta_min      5.05
_cell_volume                     1181.6(12)
_computing_cell_refinement
;
CAD-4/PC Software
;
_computing_data_collection
;
CAD-4/PC Software (Enraf--Nonius, 1993)
;
_computing_data_reduction        'XCAD (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2004)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2126
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         1.19
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.152
_refine_ls_extinction_coef       0.031(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2058
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0425P)²+0.3902P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.1029
_reflns_number_gt                1504
_reflns_number_total             2058
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc6036.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2206496
_cod_database_fobs_code          2206496
loop_
_symmetry_equiv_pos_as_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_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_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
C1 0.35489(12) 0.5497(4) 0.97169(16) 0.0427(5) Uani d . 1 C
H1 0.3183 0.6784 0.9575 0.051 Uiso calc R 1 H
N2 0.40545(11) 0.5005(4) 1.06606(14) 0.0490(5) Uani d . 1 N
N3 0.44961(11) 0.2979(4) 1.05313(13) 0.0509(5) Uani d . 1 N
C4 0.42304(13) 0.2357(4) 0.95069(16) 0.0465(5) Uani d . 1 C
H4 0.4425 0.1061 0.9191 0.056 Uiso calc R 1 H
N5 0.36322(9) 0.3861(3) 0.89694(12) 0.0368(4) Uani d . 1 N
N6 0.32277(10) 0.3864(4) 0.78542(13) 0.0400(4) Uani d . 1 N
C7 0.26956(11) 0.2132(4) 0.74386(15) 0.0361(5) Uani d . 1 C
H7 0.2597 0.1009 0.7927 0.043 Uiso calc R 1 H
C8 0.22740(11) 0.1824(4) 0.63604(14) 0.0339(4) Uani d . 1 C
C9 0.17387(13) -0.0279(4) 0.60775(17) 0.0444(5) Uani d . 1 C
O9 0.16466(11) -0.1838(3) 0.66980(13) 0.0709(6) Uani d . 1 O
O10 0.13246(8) -0.0530(3) 0.49951(11) 0.0483(4) Uani d . 1 O
C11 0.12131(11) 0.1637(4) 0.43119(15) 0.0397(5) Uani d . 1 C
O12 0.19482(8) 0.2884(3) 0.44785(10) 0.0428(4) Uani d . 1 O
C13 0.23999(11) 0.3376(4) 0.55254(15) 0.0357(5) Uani d . 1 C
O13 0.28936(8) 0.4991(3) 0.56709(11) 0.0479(4) Uani d . 1 O
C111 0.06421(13) 0.3383(5) 0.45610(19) 0.0543(6) Uani d . 1 C
H11A 0.0152 0.2540 0.4445 0.082 Uiso calc R 1 H
H11B 0.0562 0.4812 0.4089 0.082 Uiso calc R 1 H
H11C 0.0847 0.3916 0.5308 0.082 Uiso calc R 1 H
C112 0.09524(15) 0.0712(5) 0.31547(17) 0.0624(7) Uani d . 1 C
H11D 0.0460 -0.0138 0.3002 0.094 Uiso calc R 1 H
H11E 0.1338 -0.0419 0.3056 0.094 Uiso calc R 1 H
H11F 0.0893 0.2102 0.2666 0.094 Uiso calc R 1 H
O1W 0.40935(10) 0.7898(3) 0.76790(13) 0.0551(5) Uani d . 1 O
H6 0.3378(13) 0.499(5) 0.7489(18) 0.052(7) Uiso d . 1 H
H1WA 0.4116(15) 0.856(5) 0.704(2) 0.073(8) Uiso d . 1 H
H1WB 0.462(2) 0.769(7) 0.815(3) 0.110(11) Uiso d . 1 H
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
N2 C1 N5 109.7(2)
N2 C1 H1 125.1
N5 C1 H1 125.1
C1 N2 N3 107.60(17)
C4 N3 N2 106.64(17)
N3 C4 N5 110.1(2)
N3 C4 H4 124.9
N5 C4 H4 124.9
C4 N5 C1 105.89(17)
C4 N5 N6 126.95(17)
C1 N5 N6 126.95(18)
C7 N6 N5 119.46(18)
C7 N6 H6 125.8(15)
N5 N6 H6 114.7(15)
N6 C7 C8 126.42(19)
N6 C7 H7 116.8
C8 C7 H7 116.8
C7 C8 C13 121.80(18)
C7 C8 C9 117.19(18)
C13 C8 C9 120.80(17)
O9 C9 O10 117.9(2)
O9 C9 C8 126.3(2)
O10 C9 C8 115.77(18)
C9 O10 C11 118.32(16)
O10 C11 O12 110.17(16)
O10 C11 C111 110.00(17)
O12 C11 C111 109.92(18)
O10 C11 C112 106.52(19)
O12 C11 C112 106.28(17)
C111 C11 C112 113.83(19)
C13 O12 C11 117.76(14)
O13 C13 O12 117.78(17)
O13 C13 C8 125.57(18)
O12 C13 C8 116.56(17)
C11 C111 H11A 109.5
C11 C111 H11B 109.5
H11A C111 H11B 109.5
C11 C111 H11C 109.5
H11A C111 H11C 109.5
H11B C111 H11C 109.5
C11 C112 H11D 109.5
C11 C112 H11E 109.5
H11D C112 H11E 109.5
C11 C112 H11F 109.5
H11D C112 H11F 109.5
H11E C112 H11F 109.5
H1WA O1W H1WB 107(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.293(3)
C1 N5 1.348(3)
C1 H1 0.9300
N2 N3 1.387(3)
N3 C4 1.299(3)
C4 N5 1.346(3)
C4 H4 0.9300
N5 N6 1.391(2)
N6 C7 1.317(3)
N6 H6 0.86(2)
C7 C8 1.367(3)
C7 H7 0.9300
C8 C13 1.437(3)
C8 C9 1.451(3)
C9 O9 1.207(3)
C9 O10 1.365(2)
O10 C11 1.433(3)
C11 O12 1.436(2)
C11 C111 1.500(3)
C11 C112 1.502(3)
O12 C13 1.362(2)
C13 O13 1.211(2)
C111 H11A 0.9600
C111 H11B 0.9600
C111 H11C 0.9600
C112 H11D 0.9600
C112 H11E 0.9600
C112 H11F 0.9600
O1W H1WA 0.91(3)
O1W H1WB 0.96(4)
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
N6 H6 O13 . 0.86(2) 2.23(2) 2.759(2) 119.6(19)
N6 H6 O1W . 0.86(2) 1.99(2) 2.717(3) 142(2)
O1W H1WA N2 4_575 0.91(3) 1.92(3) 2.822(3) 174(2)
O1W H1WB N3 3_667 0.96(4) 1.95(4) 2.872(3) 160(3)
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
N5 C1 N2 N3 0.6(2)
C1 N2 N3 C4 0.1(2)
N2 N3 C4 N5 -0.8(2)
N3 C4 N5 C1 1.1(2)
N3 C4 N5 N6 176.18(19)
N2 C1 N5 C4 -1.1(2)
N2 C1 N5 N6 -176.12(19)
C4 N5 N6 C7 77.5(3)
C1 N5 N6 C7 -108.4(2)
N5 N6 C7 C8 -177.18(19)
N6 C7 C8 C13 2.8(3)
N6 C7 C8 C9 177.56(19)
C7 C8 C9 O9 -2.6(3)
C13 C8 C9 O9 172.2(2)
C7 C8 C9 O10 179.79(18)
C13 C8 C9 O10 -5.4(3)
O9 C9 O10 C11 159.2(2)
C8 C9 O10 C11 -23.0(3)
C9 O10 C11 O12 49.5(2)
C9 O10 C11 C111 -71.8(2)
C9 O10 C11 C112 164.38(18)
O10 C11 O12 C13 -49.7(2)
C111 C11 O12 C13 71.7(2)
C112 C11 O12 C13 -164.71(18)
C11 O12 C13 O13 -159.60(18)
C11 O12 C13 C8 23.6(3)
C7 C8 C13 O13 3.1(3)
C9 C8 C13 O13 -171.5(2)
C7 C8 C13 O12 179.60(18)
C9 C8 C13 O12 5.0(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21129089
2 PubChem 129880873
