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#$Date: 2022-07-23 06:54:42 +0300 (Sat, 23 Jul 2022) $
#$Revision: 276892 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/26/2022649.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_2022649
loop_
_publ_author_name
'Jeyaraman Selvaraj, Nirmalram'
'Sathya, Udhayasuriyan'
'Gomathi, Sundaramoorthy'
'Jegan Jennifer, Samson'
'Mathivathanan, Logesh'
'Abdul Razak, Ibrahim'
_publ_section_title
;
 Synthesis, crystal structure determination and Hirshfeld surface analysis
 of three new salt forms of creatinine with hydrobromic acid,
 3-aminobenzoic acid and 3,5-dinitrobenzoic acid
;
_journal_coeditor_code           DG3030
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229622006684
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C7 H3 N2 O6 +, C4 H8 N3 O -'
_chemical_formula_moiety         'C7 H3 N2 O6 +, C4 H8 N3 O -'
_chemical_formula_sum            'C11 H11 N5 O7'
_chemical_formula_weight         325.25
_chemical_name_common
;
Creatininium 3,5-dinitrobenzoate
;
_chemical_name_systematic
;
2-Amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-3-ium 3,5-dinitrobenzoate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 98.696(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4175(8)
_cell_length_b                   22.634(3)
_cell_length_c                   11.3668(16)
_cell_measurement_reflns_used    3163
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.8
_cell_volume                     1377.8(3)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX2 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020), Mercury (Macrae et al., 2020)
and POVRay (Cason, 2004)
;
_computing_publication_material
;
PLATON (Spek, 2020) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0374
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20448
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.545
_diffrn_reflns_theta_min         1.799
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.8664
_exptl_absorpt_correction_T_min  0.5857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            'COLOUR LESS'
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.323
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3163
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0653
_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)+(0.0937P)²+1.0476P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1786
_refine_ls_wR_factor_ref         0.1961
_reflns_number_gt                2272
_reflns_number_total             3163
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dg3030sup1.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2022649
_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   0.964
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 C4 -0.3894(5) 0.67552(12) 0.7844(2) 0.0424(6) Uani d 1 . .
H H4A -0.558043 0.685231 0.796735 0.051 Uiso calc 1 . .
H H4B -0.392828 0.639390 0.738318 0.051 Uiso calc 1 . .
C C5 -0.2733(5) 0.72557(12) 0.7240(2) 0.0427(6) Uani d 1 . .
C C2 -0.0405(4) 0.70851(10) 0.9023(2) 0.0350(5) Uani d 1 . .
C C3 -0.2620(5) 0.62719(12) 0.9871(2) 0.0483(6) Uani d 1 . .
H H3B -0.129434 0.630486 1.053120 0.072 Uiso calc 1 . .
H H3C -0.262564 0.588098 0.954290 0.072 Uiso calc 1 . .
H H3A -0.419004 0.634623 1.013773 0.072 Uiso calc 1 . .
N N8 0.9177(6) 1.01956(13) 0.7037(3) 0.0736(8) Uani d 1 . .
C C11 0.7730(4) 0.87486(11) 0.9151(2) 0.0393(5) Uani d 1 . .
H H11 0.743572 0.843176 0.963179 0.047 Uiso calc 1 . .
C C6 0.6068(4) 0.88805(10) 0.8141(2) 0.0375(5) Uani d 1 . .
C C8 0.8648(5) 0.96901(11) 0.7773(2) 0.0472(6) Uani d 1 . .
C C10 0.9834(4) 0.90935(11) 0.9437(2) 0.0414(6) Uani d 1 . .
C C7 0.6512(5) 0.93614(11) 0.7447(2) 0.0437(6) Uani d 1 . .
H H6 0.538901 0.946056 0.677449 0.052 Uiso calc 1 . .
C C9 1.0353(5) 0.95663(12) 0.8765(2) 0.0473(6) Uani d 1 . .
H H8 1.178680 0.979244 0.896870 0.057 Uiso calc 1 . .
N N3 -0.2244(4) 0.66995(9) 0.89681(17) 0.0392(5) Uani d 1 . .
N N1 -0.0656(4) 0.74201(10) 0.80206(19) 0.0413(5) Uani d 1 . .
N N2 0.1457(4) 0.71462(10) 0.98893(19) 0.0463(5) Uani d 1 . .
H H2A 0.156560 0.692065 1.050385 0.069 Uiso calc 1 . .
H H2B 0.257351 0.741190 0.984511 0.069 Uiso calc 1 . .
C C12 0.3804(5) 0.84969(12) 0.7774(2) 0.0441(6) Uani d 1 . .
N N10 1.1616(4) 0.89413(11) 1.0507(2) 0.0552(6) Uani d 1 . .
O O5 -0.3441(4) 0.74696(10) 0.62776(17) 0.0607(6) Uani d 1 . .
O O1 0.3484(4) 0.80812(10) 0.8451(2) 0.0662(6) Uani d 1 . .
O O2 0.2439(4) 0.86212(10) 0.68288(18) 0.0627(6) Uani d 1 . .
O O6 1.3477(4) 0.92497(11) 1.0742(2) 0.0732(7) Uani d 1 . .
O O7 1.1140(5) 0.85160(13) 1.1091(2) 0.0908(9) Uani d 1 . .
O O3 0.7738(7) 1.02949(15) 0.6138(3) 0.1128(12) Uani d 1 . .
O O4 1.1050(7) 1.04788(15) 0.7360(3) 0.1269(14) Uani d 1 . .
H H1 0.036(7) 0.7666(16) 0.799(3) 0.076(12) Uiso d 1 . .
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 C4 C5 . . 102.84(19) ?
N3 C4 H4A . . 111.2 ?
C5 C4 H4A . . 111.2 ?
N3 C4 H4B . . 111.2 ?
C5 C4 H4B . . 111.2 ?
H4A C4 H4B . . 109.1 ?
O5 C5 N1 . . 126.5(3) ?
O5 C5 C4 . . 128.1(2) ?
N1 C5 C4 . . 105.4(2) ?
N2 C2 N3 . . 126.7(2) ?
N2 C2 N1 . . 122.8(2) ?
N3 C2 N1 . . 110.5(2) ?
N3 C3 H3B . . 109.5 ?
N3 C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
N3 C3 H3A . . 109.5 ?
H3B C3 H3A . . 109.5 ?
H3C C3 H3A . . 109.5 ?
O3 N8 O4 . . 124.2(3) ?
O3 N8 C8 . . 118.0(3) ?
O4 N8 C8 . . 117.8(3) ?
C10 C11 C6 . . 119.0(2) ?
C10 C11 H11 . . 120.5 ?
C6 C11 H11 . . 120.5 ?
C11 C6 C7 . . 119.7(2) ?
C11 C6 C12 . . 120.4(2) ?
C7 C6 C12 . . 119.9(2) ?
C9 C8 C7 . . 122.9(3) ?
C9 C8 N8 . . 117.4(3) ?
C7 C8 N8 . . 119.7(3) ?
C9 C10 C11 . . 122.9(2) ?
C9 C10 N10 . . 118.6(2) ?
C11 C10 N10 . . 118.5(2) ?
C8 C7 C6 . . 118.8(2) ?
C8 C7 H6 . . 120.6 ?
C6 C7 H6 . . 120.6 ?
C10 C9 C8 . . 116.6(2) ?
C10 C9 H8 . . 121.7 ?
C8 C9 H8 . . 121.7 ?
C2 N3 C3 . . 126.6(2) ?
C2 N3 C4 . . 110.2(2) ?
C3 N3 C4 . . 123.3(2) ?
C2 N1 C5 . . 111.0(2) ?
C2 N1 H1 . . 117(3) ?
C5 N1 H1 . . 132(3) ?
C2 N2 H2A . . 120.0 ?
C2 N2 H2B . . 120.0 ?
H2A N2 H2B . . 120.0 ?
O2 C12 O1 . . 125.9(3) ?
O2 C12 C6 . . 117.5(3) ?
O1 C12 C6 . . 116.6(2) ?
O7 N10 O6 . . 124.6(3) ?
O7 N10 C10 . . 117.9(2) ?
O6 N10 C10 . . 117.5(3) ?
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
C4 N3 . 1.450(3) ?
C4 C5 . 1.511(4) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 O5 . 1.204(3) ?
C5 N1 . 1.375(3) ?
C2 N2 . 1.306(3) ?
C2 N3 . 1.319(3) ?
C2 N1 . 1.358(3) ?
C3 N3 . 1.447(3) ?
C3 H3B . 0.9600 ?
C3 H3C . 0.9600 ?
C3 H3A . 0.9600 ?
N8 O3 . 1.209(4) ?
N8 O4 . 1.210(4) ?
N8 C8 . 1.471(4) ?
C11 C10 . 1.379(3) ?
C11 C6 . 1.381(3) ?
C11 H11 . 0.9300 ?
C6 C7 . 1.386(4) ?
C6 C12 . 1.509(3) ?
C8 C9 . 1.374(4) ?
C8 C7 . 1.378(4) ?
C10 C9 . 1.369(4) ?
C10 N10 . 1.475(3) ?
C7 H6 . 0.9300 ?
C9 H8 . 0.9300 ?
N1 H1 . 0.79(4) ?
N2 H2A . 0.8600 ?
N2 H2B . 0.8600 ?
C12 O2 . 1.241(3) ?
C12 O1 . 1.244(3) ?
N10 O7 . 1.219(3) ?
N10 O6 . 1.223(3) ?
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
N1 H1 O1 . 0.79(4) 1.94(4) 2.679(3) 157(3)
N2 H2B O1 . 0.86 2.30 2.983(3) 137
N2 H2B O5 4_676 0.86 2.51 3.093(3) 125
N2 H2A O2 4_576 0.86 1.94 2.794(3) 169
C3 H3B O2 4_576 0.96 2.32 3.268(3) 168
C4 H4B O4 2_646 0.97 2.58 3.299(4) 131
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 C4 C5 O5 . . . . -179.6(3) ?
N3 C4 C5 N1 . . . . 0.7(3) ?
C10 C11 C6 C7 . . . . -1.3(4) ?
C10 C11 C6 C12 . . . . 177.4(2) ?
O3 N8 C8 C9 . . . . 177.2(3) ?
O4 N8 C8 C9 . . . . -1.4(5) ?
O3 N8 C8 C7 . . . . -2.4(5) ?
O4 N8 C8 C7 . . . . 179.0(4) ?
C6 C11 C10 C9 . . . . 0.3(4) ?
C6 C11 C10 N10 . . . . -179.0(2) ?
C9 C8 C7 C6 . . . . -0.7(4) ?
N8 C8 C7 C6 . . . . 178.9(2) ?
C11 C6 C7 C8 . . . . 1.4(4) ?
C12 C6 C7 C8 . . . . -177.3(2) ?
C11 C10 C9 C8 . . . . 0.4(4) ?
N10 C10 C9 C8 . . . . 179.7(2) ?
C7 C8 C9 C10 . . . . -0.2(4) ?
N8 C8 C9 C10 . . . . -179.8(2) ?
N2 C2 N3 C3 . . . . 1.7(4) ?
N1 C2 N3 C3 . . . . -179.4(2) ?
N2 C2 N3 C4 . . . . -177.8(2) ?
N1 C2 N3 C4 . . . . 1.1(3) ?
C5 C4 N3 C2 . . . . -1.1(3) ?
C5 C4 N3 C3 . . . . 179.4(2) ?
N2 C2 N1 C5 . . . . 178.4(2) ?
N3 C2 N1 C5 . . . . -0.6(3) ?
O5 C5 N1 C2 . . . . -179.8(3) ?
C4 C5 N1 C2 . . . . -0.1(3) ?
C11 C6 C12 O2 . . . . -176.7(2) ?
C7 C6 C12 O2 . . . . 2.0(4) ?
C11 C6 C12 O1 . . . . 3.0(4) ?
C7 C6 C12 O1 . . . . -178.3(2) ?
C9 C10 N10 O7 . . . . -179.4(3) ?
C11 C10 N10 O7 . . . . 0.0(4) ?
C9 C10 N10 O6 . . . . 0.2(4) ?
C11 C10 N10 O6 . . . . 179.6(3) ?

_cod_database_fobs_code 2022649
