#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/48/2214899.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_2214899
loop_
_publ_author_name
'Graham Smith'
'Urs D. Wermuth'
'Peter C. Healy'
_publ_section_title
;
 Guanidinium 2-carboxy-6-nitrobenzoate monohydrate: a two-dimensional
 hydrogen-bonded network structure
;
_journal_coeditor_code           WN2170
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3527
_journal_page_last               o3528
_journal_paper_doi               10.1107/S1600536807034356
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C H6 N3 + , C8 H4 N O6 - , H2 O'
_chemical_formula_moiety         'C H6 N3 + , C8 H4 N O6 - , H2 O'
_chemical_formula_sum            'C9 H12 N4 O7'
_chemical_formula_weight         288.23
_chemical_melting_point          .395E-305
_chemical_name_common
'guanidinium hydrogen 3-nitrophthalate monohydrate'
_chemical_name_systematic
;
guanidinium 2-carboxy-6-nitrobenzoate monohydrate
;
_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           'SHELXL97 (Sheldrick, 1997)'
_cell_angle_alpha                90.00
_cell_angle_beta                 100.006(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.758(3)
_cell_length_b                   12.5955(19)
_cell_length_c                   6.8423(12)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      17.5
_cell_measurement_theta_min      12.6
_cell_volume                     1252.5(4)
_computing_cell_refinement       'MSC/AFC Diffractmeter Control Software'
_computing_data_collection
;
MSC/AFC Diffractmeter Control Software (Molecular Structure
Corporation, 1999)
;
_computing_data_reduction
;
TEXSAN for Windows (Molecular Structure Corporation, 1999)
;
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  PLATON
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku AFC-7R'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3307
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.80
_diffrn_standards_decay_%        1.2
_diffrn_standards_interval_time  150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.9739
_exptl_absorpt_correction_T_min  0.9487
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
'(TEXSAN for Windows; Molecular Structure Corporation, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_description       'cut block'
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.403
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.86
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.86
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1P)²+5.5554P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1466
_reflns_number_gt                2080
_reflns_number_total             2872
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn2170.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2214899
_cod_database_fobs_code          2214899
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_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_occupancy
O O11A 0.33502(12) 1.28306(13) 0.6829(3) 0.0402(6) Uani 1.000
O O11B 0.21101(11) 1.19235(14) 0.5452(3) 0.0436(6) Uani 1.000
O O21A 0.16688(11) 0.96584(13) 0.4120(2) 0.0331(5) Uani 1.000
O O21B 0.16155(10) 0.98708(14) 0.7330(2) 0.0339(5) Uani 1.000
O O31A 0.25485(12) 0.78120(15) 0.6336(3) 0.0480(6) Uani 1.000
O O31B 0.38515(13) 0.73913(16) 0.5523(3) 0.0551(7) Uani 1.000
N N31 0.33335(13) 0.80279(15) 0.6115(3) 0.0338(6) Uani 1.000
C C1 0.34791(14) 1.09732(17) 0.6688(3) 0.0266(6) Uani 1.000
C C2 0.30745(13) 0.99645(16) 0.6370(3) 0.0240(5) Uani 1.000
C C3 0.36807(14) 0.91080(17) 0.6560(3) 0.0270(6) Uani 1.000
C C4 0.46275(15) 0.92106(19) 0.7140(4) 0.0337(7) Uani 1.000
C C5 0.50006(15) 1.0204(2) 0.7553(4) 0.0374(7) Uani 1.000
C C6 0.44276(15) 1.10785(19) 0.7288(4) 0.0346(7) Uani 1.000
C C11 0.29065(15) 1.19500(17) 0.6278(3) 0.0283(6) Uani 1.000
C C21 0.20296(13) 0.98198(16) 0.5881(3) 0.0250(6) Uani 1.000
N N12 0.08940(15) 0.7473(2) 0.8170(3) 0.0406(7) Uani 1.000
N N22 -0.05841(16) 0.6993(2) 0.6799(4) 0.0454(7) Uani 1.000
N N32 -0.01159(16) 0.87191(19) 0.6668(4) 0.0409(7) Uani 1.000
C C12 0.00621(15) 0.77276(19) 0.7218(3) 0.0313(6) Uani 1.000
O O1W 0.25121(17) 1.04247(17) 1.1102(4) 0.0536(7) Uani 1.000
H H4 0.50130 0.86020 0.72510 0.0400 Uiso 1.000
H H5 0.56420 1.02870 0.80120 0.0450 Uiso 1.000
H H6 0.46850 1.17680 0.75190 0.0420 Uiso 1.000
H H11A 0.299(3) 1.340(3) 0.655(5) 0.069(11) Uiso 1.000
H H12A 0.104(2) 0.678(3) 0.838(5) 0.055(9) Uiso 1.000
H H12B 0.130(2) 0.796(3) 0.839(5) 0.056(10) Uiso 1.000
H H22A -0.113(3) 0.720(3) 0.605(6) 0.071(11) Uiso 1.000
H H22B -0.050(2) 0.637(3) 0.733(5) 0.056(9) Uiso 1.000
H H32A 0.030(2) 0.917(3) 0.683(5) 0.058(10) Uiso 1.000
H H32B -0.066(3) 0.894(3) 0.629(5) 0.063(10) Uiso 1.000
H H1W 0.222(3) 1.022(3) 0.994(7) 0.071(12) Uiso 1.000
H H2W 0.221(3) 1.018(3) 1.196(7) 0.078(13) 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 0.0016 '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
_geom_angle_publ_flag
C11 O11A H11A 112(3) no
H1W O1W H2W 107(4) no
O31A N31 C3 118.95(19) no
O31A N31 O31B 123.6(2) no
O31B N31 C3 117.41(19) no
C12 N12 H12B 118(2) no
C12 N12 H12A 119(2) no
H12A N12 H12B 122(3) no
H22A N22 H22B 123(3) no
C12 N22 H22A 117(2) no
C12 N22 H22B 120(2) no
H32A N32 H32B 117(3) no
C12 N32 H32B 122(3) no
C12 N32 H32A 120(2) no
C2 C1 C6 120.6(2) no
C6 C1 C11 118.9(2) no
C2 C1 C11 120.35(19) no
C3 C2 C21 122.30(18) no
C1 C2 C3 115.93(18) no
C1 C2 C21 121.77(18) no
C2 C3 C4 123.5(2) no
N31 C3 C4 116.29(19) no
N31 C3 C2 120.22(18) no
C3 C4 C5 119.3(2) no
C4 C5 C6 119.0(2) no
C1 C6 C5 121.5(2) no
O11A C11 O11B 123.6(2) no
O11A C11 C1 113.95(19) no
O11B C11 C1 122.4(2) no
O21A C21 C2 118.40(18) no
O21B C21 C2 115.60(17) no
O21A C21 O21B 126.01(19) no
C3 C4 H4 120.00 no
C5 C4 H4 120.00 no
C6 C5 H5 121.00 no
C4 C5 H5 121.00 no
C5 C6 H6 119.00 no
C1 C6 H6 119.00 no
N12 C12 N22 120.6(2) no
N12 C12 N32 119.4(2) no
N22 C12 N32 120.0(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O11A C11 1.310(3) no
O11B C11 1.213(3) no
O21A C21 1.247(2) no
O21B C21 1.253(2) no
O31A N31 1.225(3) no
O31B N31 1.224(3) no
O11A H11A 0.89(4) no
O1W H1W 0.88(5) no
O1W H2W 0.85(5) no
N31 C3 1.467(3) no
N12 C12 1.325(3) no
N22 C12 1.324(3) no
N32 C12 1.318(3) no
N12 H12B 0.85(4) no
N12 H12A 0.91(4) no
N22 H22B 0.87(4) no
N22 H22A 0.91(4) no
N32 H32B 0.85(4) no
N32 H32A 0.83(3) no
C1 C6 1.395(3) no
C1 C11 1.491(3) no
C1 C2 1.405(3) no
C2 C3 1.393(3) no
C2 C21 1.531(3) no
C3 C4 1.391(3) no
C4 C5 1.376(3) no
C5 C6 1.381(3) no
C4 H4 0.9500 no
C5 H5 0.9500 no
C6 H6 0.9500 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
O1W H1W O21B . 0.88(5) 1.90(5) 2.777(3) 176(3) yes
O1W H2W O21A 1_556 0.85(5) 1.91(5) 2.764(3) 173(4) yes
O11A H11A O1W 4_574 0.89(4) 1.65(4) 2.528(3) 169(4) yes
N12 H12A O21A 4_565 0.91(4) 2.06(4) 2.946(3) 167(3) yes
N12 H12B O21B . 0.85(4) 2.58(4) 3.286(3) 141(3) yes
N12 H12B O31A . 0.85(4) 2.51(3) 2.964(3) 114(3) yes
N22 H22A O11B 3_576 0.91(4) 1.96(4) 2.846(3) 162(3) yes
N22 H22B O21B 2_546 0.87(4) 2.54(3) 3.183(3) 132(3) yes
N32 H32A O21B . 0.83(3) 2.11(3) 2.905(3) 162(3) yes
N32 H32B O11B 3_576 0.85(4) 2.51(4) 3.152(3) 134(3) yes
N32 H32B O21A 3_576 0.85(4) 2.30(4) 3.048(3) 148(3) yes
C4 H4 O11A 2_646 0.9500 2.5800 3.420(3) 148.00 no
C6 H6 O11A . 0.9500 2.3600 2.706(3) 101.00 no
C6 H6 O31B 2_656 0.9500 2.4600 3.179(3) 132.00 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
_geom_torsion_publ_flag
O31A N31 C3 C2 -28.2(3) no
O31A N31 C3 C4 152.5(2) no
O31B N31 C3 C2 151.2(2) no
O31B N31 C3 C4 -28.0(3) no
C6 C1 C2 C3 -4.2(3) no
C6 C1 C2 C21 174.8(2) no
C11 C1 C2 C3 172.36(18) no
C11 C1 C2 C21 -8.7(3) no
C2 C1 C6 C5 1.2(4) no
C11 C1 C6 C5 -175.4(2) no
C2 C1 C11 O11A 173.34(19) no
C2 C1 C11 O11B -8.8(3) no
C6 C1 C11 O11A -10.1(3) no
C6 C1 C11 O11B 167.8(2) no
C1 C2 C3 N31 -175.49(18) no
C1 C2 C3 C4 3.7(3) no
C21 C2 C3 N31 5.6(3) no
C21 C2 C3 C4 -175.3(2) no
C1 C2 C21 O21A 101.2(2) no
C1 C2 C21 O21B -79.2(3) no
C3 C2 C21 O21A -79.9(3) no
C3 C2 C21 O21B 99.7(2) no
N31 C3 C4 C5 179.1(2) no
C2 C3 C4 C5 -0.1(4) no
C3 C4 C5 C6 -3.1(4) no
C4 C5 C6 C1 2.5(4) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139072828
