#------------------------------------------------------------------------------
#$Date: 2021-07-01 08:11:34 +0300 (Thu, 01 Jul 2021) $
#$Revision: 266841 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/38/2243860.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_2243860
loop_
_publ_author_name
'Atioğlu, Zeliha'
'Akkurt, Mehmet'
'Mammadova, Gunay Z.'
'Huseynov, Fatali E.'
'Hajiyeva, Sevinj R.'
'Shamilov, Nazim T.'
'Bhattarai, Ajaya'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of dimethyl
 5-[2-(2,4,6-trioxo-1,3-diazinan-5-ylidene)hydrazin-1-yl]benzene-1,3-dicarboxylate
 0.224-hydrate
;
_journal_coeditor_code           YK2153
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              759
_journal_page_last               764
_journal_paper_doi               10.1107/S2056989021006563
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C14 H12 N4 O7, 0.224H2 O'
_chemical_formula_moiety         'C14 H12 N4 O7, 0.224(H2O)'
_chemical_formula_sum            'C14 H12.448 N4 O7.224'
_chemical_formula_weight         351.86
_chemical_name_systematic
;Dimethyl
5-[2-(2,4,6-trioxo-1,3-diazinan-5-ylidene)hydrazin-1-yl]benzene-1,3-dicarboxylate 0.224-hydrate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 113.133(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.2097(11)
_cell_length_b                   12.6311(6)
_cell_length_c                   10.4022(5)
_cell_measurement_reflns_used    9840
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      3.23
_cell_volume                     2925.2(2)
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_collection
;
APEX2 (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_unetI/netI     0.0078
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            34832
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.378
_diffrn_reflns_theta_min         3.226
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_description       block
_exptl_crystal_F_000             1454
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.270
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         2944
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0340
_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/[σ²(Fo²)+(0.0586P)²+2.1077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                2699
_reflns_number_total             2944
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yk2153sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2243860
_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_estimated_absorpt_t_min   0.957
_shelx_estimated_absorpt_t_max   0.965
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 0.37057(5) 0.39423(9) 0.82909(12) 0.0190(2) Uani d 1 . .
C C2 0.37833(5) 0.39902(9) 0.97648(12) 0.0207(2) Uani d 1 . .
C C3 0.48693(5) 0.37742(9) 1.04270(12) 0.0208(2) Uani d 1 . .
C C4 0.42279(5) 0.38365(8) 0.79361(12) 0.0186(2) Uani d 1 . .
C C5 0.24165(5) 0.38344(8) 0.50833(12) 0.0192(2) Uani d 1 . .
C C6 0.23130(5) 0.37794(9) 0.36716(12) 0.0204(2) Uani d 1 . .
H H6 0.263906 0.380695 0.338172 0.025 Uiso calc 1 . .
C C7 0.17254(5) 0.36834(9) 0.26874(11) 0.0197(2) Uani d 1 . .
C C8 0.12459(5) 0.36539(9) 0.31079(12) 0.0201(2) Uani d 1 . .
H H8 0.084612 0.358679 0.243355 0.024 Uiso calc 1 . .
C C9 0.13569(5) 0.37237(9) 0.45277(12) 0.0200(2) Uani d 1 . .
C C10 0.19423(5) 0.38111(9) 0.55282(12) 0.0203(2) Uani d 1 . .
H H10 0.201704 0.385399 0.649417 0.024 Uiso calc 1 . .
C C11 0.15859(5) 0.35937(9) 0.11562(12) 0.0211(2) Uani d 1 . .
C C12 0.19700(5) 0.35182(11) -0.05977(12) 0.0264(3) Uani d 1 . .
H H12A 0.177183 0.284238 -0.096410 0.040 Uiso calc 1 . .
H H12B 0.235389 0.355077 -0.070599 0.040 Uiso calc 1 . .
H H12C 0.171209 0.410245 -0.111573 0.040 Uiso calc 1 . .
C C13 0.08236(5) 0.37078(10) 0.49220(12) 0.0231(3) Uani d 1 . .
C C14 0.04671(6) 0.39831(12) 0.66992(14) 0.0307(3) Uani d 1 . .
H H14A 0.022390 0.461429 0.630597 0.046 Uiso calc 1 . .
H H14B 0.062181 0.401216 0.772194 0.046 Uiso calc 1 . .
H H14C 0.021864 0.334851 0.636695 0.046 Uiso calc 1 . .
N N1 0.43716(4) 0.38898(8) 1.07229(10) 0.0215(2) Uani d 1 . .
H H1N 0.445330 0.388946 1.160377 0.026(4) Uiso d 1 . .
N N2 0.47752(4) 0.37483(8) 0.90340(10) 0.0209(2) Uani d 1 . .
H H2N 0.510968 0.367522 0.886519 0.032(4) Uiso d 1 . .
N N3 0.31416(4) 0.39456(7) 0.73771(10) 0.0197(2) Uani d 1 . .
N N4 0.30173(4) 0.38952(8) 0.60489(10) 0.0202(2) Uani d 1 . .
H H4N 0.329280 0.391432 0.572748 0.041(5) Uiso d 1 . .
O O1 0.33809(4) 0.41106(8) 1.01707(9) 0.0285(2) Uani d 1 . .
O O2 0.53768(4) 0.37191(8) 1.13392(9) 0.0279(2) Uani d 1 . .
O O3 0.41946(4) 0.38163(7) 0.67172(8) 0.0229(2) Uani d 1 . .
O O4 0.10827(4) 0.35077(8) 0.02776(9) 0.0310(2) Uani d 1 . .
O O5 0.20773(4) 0.36060(7) 0.08791(8) 0.0250(2) Uani d 1 . .
O O6 0.03258(4) 0.35068(10) 0.41153(10) 0.0431(3) Uani d 1 . .
O O7 0.09668(4) 0.39450(8) 0.62583(9) 0.0292(2) Uani d 1 . .
O OW1 0.3463(2) 0.3484(4) 0.3151(6) 0.0466(19) Uani d 0.224(5) . .
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
N3 C1 C4 . . 124.93(10) ?
N3 C1 C2 . . 114.97(10) ?
C4 C1 C2 . . 120.00(10) ?
O1 C2 N1 . . 119.97(10) ?
O1 C2 C1 . . 125.19(10) ?
N1 C2 C1 . . 114.84(9) ?
O2 C3 N1 . . 122.53(10) ?
O2 C3 N2 . . 121.04(10) ?
N1 C3 N2 . . 116.41(10) ?
O3 C4 N2 . . 120.22(10) ?
O3 C4 C1 . . 123.21(10) ?
N2 C4 C1 . . 116.56(10) ?
C6 C5 C10 . . 121.20(10) ?
C6 C5 N4 . . 117.59(10) ?
C10 C5 N4 . . 121.20(10) ?
C5 C6 C7 . . 119.25(10) ?
C5 C6 H6 . . 120.4 ?
C7 C6 H6 . . 120.4 ?
C8 C7 C6 . . 120.52(10) ?
C8 C7 C11 . . 117.69(10) ?
C6 C7 C11 . . 121.79(10) ?
C7 C8 C9 . . 119.52(10) ?
C7 C8 H8 . . 120.2 ?
C9 C8 H8 . . 120.2 ?
C10 C9 C8 . . 120.75(11) ?
C10 C9 C13 . . 121.89(10) ?
C8 C9 C13 . . 117.35(10) ?
C9 C10 C5 . . 118.75(10) ?
C9 C10 H10 . . 120.6 ?
C5 C10 H10 . . 120.6 ?
O4 C11 O5 . . 124.04(10) ?
O4 C11 C7 . . 123.45(10) ?
O5 C11 C7 . . 112.50(9) ?
O5 C12 H12A . . 109.5 ?
O5 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
O5 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
O6 C13 O7 . . 124.04(11) ?
O6 C13 C9 . . 123.36(11) ?
O7 C13 C9 . . 112.60(9) ?
O7 C14 H14A . . 109.5 ?
O7 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O7 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C3 N1 C2 . . 126.63(9) ?
C3 N1 H1N . . 112.8 ?
C2 N1 H1N . . 120.6 ?
C4 N2 C3 . . 125.51(10) ?
C4 N2 H2N . . 119.7 ?
C3 N2 H2N . . 114.8 ?
N4 N3 C1 . . 120.55(10) ?
N3 N4 C5 . . 120.38(9) ?
N3 N4 H4N . . 121.7 ?
C5 N4 H4N . . 117.9 ?
C11 O5 C12 . . 115.04(9) ?
C13 O7 C14 . . 115.50(9) ?
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 N3 . 1.3223(15) ?
C1 C4 . 1.4557(16) ?
C1 C2 . 1.4708(15) ?
C2 O1 . 1.2140(14) ?
C2 N1 . 1.3864(14) ?
C3 O2 . 1.2242(14) ?
C3 N1 . 1.3638(15) ?
C3 N2 . 1.3759(15) ?
C4 O3 . 1.2387(14) ?
C4 N2 . 1.3724(14) ?
C5 C6 . 1.3909(16) ?
C5 C10 . 1.3968(16) ?
C5 N4 . 1.4080(14) ?
C6 C7 . 1.3936(16) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.3926(16) ?
C7 C11 . 1.4970(15) ?
C8 C9 . 1.3963(16) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.3945(16) ?
C9 C13 . 1.5006(16) ?
C10 H10 . 0.9500 ?
C11 O4 . 1.2068(14) ?
C11 O5 . 1.3298(14) ?
C12 O5 . 1.4581(14) ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C13 O6 . 1.1944(15) ?
C13 O7 . 1.3280(15) ?
C14 O7 . 1.4533(14) ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
N1 H1N . 0.8580 ?
N2 H2N . 0.8982 ?
N3 N4 . 1.2950(14) ?
N4 H4N . 0.8557 ?
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
_geom_hbond_publ_flag
N1 H1N O2 2_657 0.86 2.03 2.8800(13) 174 yes
N2 H2N O3 2_656 0.90 2.01 2.8931(15) 168 yes
N4 H4N O3 . 0.86 2.02 2.6571(15) 131 yes
N4 H4N O1 6_565 0.86 2.59 2.9302(14) 105 no
C6 H6 Ow1 . 0.95 2.14 3.061(6) 163 yes
C12 H12B O1 1_554 0.98 2.39 3.2743(17) 149 yes
C14 H14B O4 1_556 0.98 2.53 3.4754(16) 163 yes
C12 H12C Cg2 6_565 0.98 2.73 3.4717(15) 133 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
N3 C1 C2 O1 . . . . -5.85(17) ?
C4 C1 C2 O1 . . . . 177.58(11) ?
N3 C1 C2 N1 . . . . 174.41(9) ?
C4 C1 C2 N1 . . . . -2.17(15) ?
N3 C1 C4 O3 . . . . 5.51(18) ?
C2 C1 C4 O3 . . . . -178.27(10) ?
N3 C1 C4 N2 . . . . -173.94(10) ?
C2 C1 C4 N2 . . . . 2.27(15) ?
C10 C5 C6 C7 . . . . -0.97(16) ?
N4 C5 C6 C7 . . . . 177.91(10) ?
C5 C6 C7 C8 . . . . 0.67(16) ?
C5 C6 C7 C11 . . . . -178.47(10) ?
C6 C7 C8 C9 . . . . 0.14(16) ?
C11 C7 C8 C9 . . . . 179.32(10) ?
C7 C8 C9 C10 . . . . -0.68(16) ?
C7 C8 C9 C13 . . . . 178.92(10) ?
C8 C9 C10 C5 . . . . 0.40(16) ?
C13 C9 C10 C5 . . . . -179.18(10) ?
C6 C5 C10 C9 . . . . 0.43(16) ?
N4 C5 C10 C9 . . . . -178.40(10) ?
C8 C7 C11 O4 . . . . 0.70(17) ?
C6 C7 C11 O4 . . . . 179.87(11) ?
C8 C7 C11 O5 . . . . -178.51(10) ?
C6 C7 C11 O5 . . . . 0.66(15) ?
C10 C9 C13 O6 . . . . -170.65(13) ?
C8 C9 C13 O6 . . . . 9.75(18) ?
C10 C9 C13 O7 . . . . 9.60(16) ?
C8 C9 C13 O7 . . . . -170.00(10) ?
O2 C3 N1 C2 . . . . 177.97(11) ?
N2 C3 N1 C2 . . . . -0.46(17) ?
O1 C2 N1 C3 . . . . -178.47(11) ?
C1 C2 N1 C3 . . . . 1.29(17) ?
O3 C4 N2 C3 . . . . 179.07(11) ?
C1 C4 N2 C3 . . . . -1.46(16) ?
O2 C3 N2 C4 . . . . -177.92(11) ?
N1 C3 N2 C4 . . . . 0.53(17) ?
C4 C1 N3 N4 . . . . -2.91(17) ?
C2 C1 N3 N4 . . . . -179.30(9) ?
C1 N3 N4 C5 . . . . 176.15(10) ?
C6 C5 N4 N3 . . . . -179.84(10) ?
C10 C5 N4 N3 . . . . -0.97(16) ?
O4 C11 O5 C12 . . . . 0.65(16) ?
C7 C11 O5 C12 . . . . 179.85(9) ?
O6 C13 O7 C14 . . . . -1.96(19) ?
C9 C13 O7 C14 . . . . 177.79(10) ?

_cod_database_fobs_code 2243860
