#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/68/2226803.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_2226803
loop_
_publ_author_name
'Smith, Graham'
'Wermuth, Urs D.'
_publ_section_title
;
 Guanidinium 3-nitrobenzoate
;
_journal_coeditor_code           BV2146
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1946
_journal_paper_doi               10.1107/S160053681002581X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C H6 N3 +, C7 H4 N O4 -'
_chemical_formula_moiety         'C H6 N3 +, C7 H4 N O4 -'
_chemical_formula_sum            'C8 H10 N4 O4'
_chemical_formula_weight         226.20
_chemical_melting_point          514
_chemical_name_common            'guanidinium 3-nitrobenzoate'
_chemical_name_systematic
;
Guanidinium 3-nitrobenzoate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3978(12)
_cell_length_b                   10.1302(12)
_cell_length_c                   13.7118(17)
_cell_measurement_reflns_used    2964
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      28.94
_cell_measurement_theta_min      2.97
_cell_volume                     1027.6(2)
_computing_cell_refinement
'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_reduction
'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Oxford Diffraction Gemini-S CCD-detector diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7455
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.97
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis Pro; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.155
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         1252
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0346
_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)+(0.0716P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0960
_reflns_number_gt                1092
_reflns_number_total             1252
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bv2146.cif
_cod_data_source_block           I
_cod_database_code               2226803
_cod_database_fobs_code          2226803
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O11 0.8853(3) 0.39642(19) -0.15616(11) 0.0763(7) Uani . . 1.000
O O12 0.8391(3) 0.51830(14) -0.02410(12) 0.0587(5) Uani . . 1.000
O O31 0.9478(4) 0.2929(2) 0.29189(13) 0.0891(8) Uani . . 1.000
O O32 0.8919(4) 0.0871(2) 0.30563(13) 0.0879(8) Uani . . 1.000
N N31 0.9085(3) 0.1871(2) 0.25680(14) 0.0582(6) Uani . . 1.000
C C1 0.8552(3) 0.28643(18) -0.00456(13) 0.0395(5) Uani . . 1.000
C C2 0.8834(3) 0.29418(19) 0.09621(14) 0.0395(5) Uani . . 1.000
C C3 0.8802(3) 0.1785(2) 0.15053(15) 0.0438(6) Uani . . 1.000
C C4 0.8496(3) 0.0567(2) 0.10846(18) 0.0546(7) Uani . . 1.000
C C5 0.8224(3) 0.0507(2) 0.00897(18) 0.0579(8) Uani . . 1.000
C C6 0.8262(3) 0.1633(2) -0.04688(16) 0.0487(6) Uani . . 1.000
C C11 0.8592(3) 0.4098(2) -0.06632(14) 0.0472(6) Uani . . 1.000
N N1G 0.5698(4) 0.7518(2) 0.02372(14) 0.0596(7) Uani . . 1.000
N N2G 0.5023(3) 0.7924(2) 0.18458(16) 0.0624(7) Uani . . 1.000
N N3G 0.6559(3) 0.6050(2) 0.14213(17) 0.0599(7) Uani . . 1.000
C C1G 0.5763(3) 0.7166(2) 0.11723(14) 0.0468(6) Uani . . 1.000
H H2 0.90390 0.37520 0.12620 0.0470 Uiso calc R 1.000
H H4 0.84730 -0.01950 0.14630 0.0660 Uiso calc R 1.000
H H5 0.80130 -0.03050 -0.02060 0.0690 Uiso calc R 1.000
H H6 0.80920 0.15720 -0.11390 0.0580 Uiso calc R 1.000
H H11G 0.617(4) 0.701(3) -0.015(2) 0.070(9) Uiso . . 1.000
H H12G 0.514(4) 0.821(3) 0.012(2) 0.072(8) Uiso . . 1.000
H H21G 0.444(4) 0.869(3) 0.170(2) 0.077(9) Uiso . . 1.000
H H22G 0.506(4) 0.767(3) 0.244(2) 0.065(8) Uiso . . 1.000
H H31G 0.666(4) 0.588(3) 0.203(2) 0.065(8) Uiso . . 1.000
H H32G 0.715(4) 0.563(3) 0.093(2) 0.073(9) Uiso . . 1.000
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O31 N31 O32 . . . 122.8(2) no
O31 N31 C3 . . . 118.64(19) no
O32 N31 C3 . . . 118.60(19) no
C1G N1G H12G . . . 115.5(19) no
H11G N1G H12G . . . 128(3) no
C1G N1G H11G . . . 116(2) no
H21G N2G H22G . . . 119(3) no
C1G N2G H21G . . . 122.6(18) no
C1G N2G H22G . . . 119(2) no
H31G N3G H32G . . . 126(3) no
C1G N3G H32G . . . 115.1(19) no
C1G N3G H31G . . . 118(2) no
C6 C1 C11 . . . 120.72(17) no
C2 C1 C11 . . . 120.29(17) no
C2 C1 C6 . . . 118.99(17) no
C1 C2 C3 . . . 118.66(18) no
N31 C3 C4 . . . 119.27(19) no
N31 C3 C2 . . . 118.53(18) no
C2 C3 C4 . . . 122.2(2) no
C3 C4 C5 . . . 118.4(2) no
C4 C5 C6 . . . 120.8(2) no
C1 C6 C5 . . . 121.0(2) no
O11 C11 C1 . . . 117.67(18) no
O12 C11 C1 . . . 117.73(17) no
O11 C11 O12 . . . 124.6(2) no
C3 C2 H2 . . . 121.00 no
C1 C2 H2 . . . 121.00 no
C3 C4 H4 . . . 121.00 no
C5 C4 H4 . . . 121.00 no
C4 C5 H5 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
C5 C6 H6 . . . 120.00 no
C1 C6 H6 . . . 119.00 no
N2G C1G N3G . . . 120.2(2) no
N1G C1G N2G . . . 120.2(2) no
N1G C1G N3G . . . 119.6(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O11 C11 . . 1.254(2) no
O12 C11 . . 1.251(3) no
O31 N31 . . 1.210(3) no
O32 N31 . . 1.221(3) no
N31 C3 . . 1.475(3) no
N1G C1G . . 1.332(3) no
N2G C1G . . 1.320(3) no
N3G C1G . . 1.320(3) no
N1G H12G . . 0.83(3) no
N1G H11G . . 0.82(3) no
N2G H22G . . 0.86(3) no
N2G H21G . . 0.91(3) no
N3G H31G . . 0.86(3) no
N3G H32G . . 0.91(3) no
C1 C6 . . 1.392(3) no
C1 C11 . . 1.510(3) no
C1 C2 . . 1.400(3) no
C2 C3 . . 1.389(3) no
C3 C4 . . 1.381(3) no
C4 C5 . . 1.380(3) no
C5 C6 . . 1.374(3) no
C2 H2 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C6 H6 . . 0.9300 no
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
N1G H11G O12 . 0.82(3) 2.48(3) 3.161(3) 142(3) yes
N1G H12G O12 3_465 0.83(3) 2.09(3) 2.887(3) 162(3) yes
N2G H21G O11 3_465 0.91(3) 2.42(3) 3.292(3) 160(2) yes
N2G H21G O12 3_465 0.91(3) 2.43(3) 3.159(3) 137(2) yes
N2G H22G O11 2_665 0.86(3) 2.29(3) 3.020(3) 143(3) yes
N3G H31G O11 2_665 0.86(3) 1.97(3) 2.783(3) 157(3) yes
N3G H32G O12 . 0.91(3) 1.90(3) 2.794(3) 166(3) yes
C4 H4 O31 4_745 0.93 2.57 3.355(3) 142 no
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
O31 N31 C3 C2 . . . . -5.8(3) no
O31 N31 C3 C4 . . . . 174.9(2) no
O32 N31 C3 C2 . . . . 174.4(2) no
O32 N31 C3 C4 . . . . -4.9(3) no
C6 C1 C2 C3 . . . . -0.4(3) no
C11 C1 C2 C3 . . . . -179.5(2) no
C2 C1 C6 C5 . . . . 1.0(3) no
C11 C1 C6 C5 . . . . -180.0(2) no
C2 C1 C11 O11 . . . . 160.0(2) no
C2 C1 C11 O12 . . . . -18.9(3) no
C6 C1 C11 O11 . . . . -19.1(3) no
C6 C1 C11 O12 . . . . 162.0(2) no
C1 C2 C3 N31 . . . . -179.5(2) no
C1 C2 C3 C4 . . . . -0.2(3) no
N31 C3 C4 C5 . . . . 179.6(2) no
C2 C3 C4 C5 . . . . 0.4(3) no
C3 C4 C5 C6 . . . . 0.2(3) no
C4 C5 C6 C1 . . . . -0.8(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 129865905
