#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/89/4508920.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4508920
loop_
_publ_author_name
'Eppel, Sagi'
'Bernstein, Joel'
_publ_section_title
;
 Statistics-Based Design of Multicomponent Molecular Crystals with the
 Three-Center Hydrogen Bond
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1683
_journal_paper_doi               10.1021/cg8002788
_journal_volume                  9
_journal_year                    2009
_chemical_formula_moiety         C7N1O4H4,NH4
_chemical_formula_sum            'C7 H8 N2 O4'
_chemical_formula_weight         184.15
_chemical_name_systematic        '3 NITROBENZOIC ACID , AMOUNIOM'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                85.866(6)
_cell_angle_beta                 82.325(7)
_cell_angle_gamma                81.876(7)
_cell_formula_units_Z            4
_cell_length_a                   7.038(2)
_cell_length_b                   7.596(2)
_cell_length_c                   15.973(5)
_cell_measurement_temperature    298(2)
_cell_volume                     836.6(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_measured_fraction_theta_max 0.890
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5391
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         1.29
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             384
_exptl_crystal_recrystallization_method '33% amonioum Hydroxide '
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.827
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3720
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.827
_refine_ls_R_factor_all          0.1317
_refine_ls_R_factor_gt           0.0492
_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)+(0.0544P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1273
_reflns_number_gt                1651
_reflns_number_total             3720
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg8002788sup1.cif
_cod_data_source_block           III
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'NONE' changed to 'none'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               4508920
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
O1 O 0.4972(2) 0.2054(2) 0.35773(9) 0.0515(5) Uani 1 1 d
O2 O 1.2501(2) 0.4686(2) 0.54067(10) 0.0568(5) Uani 1 1 d
O3 O 1.1318(2) 0.74514(19) 0.50352(9) 0.0472(4) Uani 1 1 d
O4 O 0.5839(3) -0.0842(2) 0.34479(9) 0.0579(5) Uani 1 1 d
N1 N 0.2618(3) 0.0946(3) 0.50267(14) 0.0418(5) Uani 1 1 d
C1 C 0.5624(3) 0.0733(3) 0.31518(13) 0.0394(6) Uani 1 1 d
C2 C 0.9874(3) 0.8086(3) 0.67281(14) 0.0401(6) Uani 1 1 d
C3 C 1.1539(3) 0.6145(3) 0.55652(14) 0.0410(6) Uani 1 1 d
N2 N 0.4147(4) 0.5874(4) 0.37060(16) 0.0547(6) Uani 1 1 d
C4 C 1.0566(3) 0.6395(3) 0.64614(13) 0.0390(6) Uani 1 1 d
N3 N 0.8384(3) 1.0076(3) 0.78356(14) 0.0569(6) Uani 1 1 d
C5 C 0.9059(3) 0.8275(3) 0.75560(14) 0.0417(6) Uani 1 1 d
C6 C 0.6209(3) 0.1050(3) 0.22161(13) 0.0403(6) Uani 1 1 d
O5 O 0.8334(3) 1.1308(2) 0.73061(12) 0.0791(6) Uani 1 1 d
C7 C 0.6189(4) 0.2754(3) 0.18648(14) 0.0463(6) Uani 1 1 d
C8 C 1.0370(4) 0.4954(3) 0.70248(16) 0.0543(7) Uani 1 1 d
O6 O 0.7918(3) 1.0263(3) 0.85871(12) 0.0969(8) Uani 1 1 d
C15 C 0.6748(4) 0.3012(3) 0.10163(14) 0.0565(7) Uani 1 1 d
C9 C 0.8859(4) 0.6837(4) 0.81186(17) 0.0558(7) Uani 1 1 d
C10 C 0.6791(4) -0.0351(4) 0.17010(16) 0.0633(8) Uani 1 1 d
C12 C 0.9497(4) 0.5167(4) 0.78415(17) 0.0647(8) Uani 1 1 d
N4 N 0.6729(5) 0.4841(4) 0.06611(16) 0.0941(10) Uani 1 1 d
O7 O 0.7440(4) 0.5081(3) -0.00622(14) 0.1384(12) Uani 1 1 d
O8 O 0.6014(5) 0.6038(3) 0.11043(16) 0.1487(13) Uani 1 1 d
C13 C 0.7297(5) 0.1637(4) 0.04998(18) 0.0790(10) Uani 1 1 d
C14 C 0.7304(6) -0.0043(4) 0.08428(18) 0.0891(11) Uani 1 1 d
H1 H 0.240(3) -0.020(3) 0.4970(14) 0.063(8) Uiso 1 1 d
H2 H 0.578(3) 0.381(3) 0.2183(14) 0.061(7) Uiso 1 1 d
H3 H 1.079(3) 0.383(3) 0.6854(13) 0.046(7) Uiso 1 1 d
H4 H 0.426(4) 0.480(4) 0.3565(17) 0.078(10) Uiso 1 1 d
H5 H 0.348(4) 0.128(3) 0.4513(17) 0.078(9) Uiso 1 1 d
H6 H 0.941(4) 0.415(3) 0.8232(15) 0.073(8) Uiso 1 1 d
H7 H 0.996(3) 0.911(3) 0.6376(13) 0.049(7) Uiso 1 1 d
H8 H 0.311(4) 0.106(3) 0.5564(17) 0.071(8) Uiso 1 1 d
H9 H 0.125(4) 0.169(4) 0.5055(17) 0.089(10) Uiso 1 1 d
H10 H 0.820(3) 0.705(3) 0.8671(16) 0.062(7) Uiso 1 1 d
H11 H 0.684(3) -0.157(3) 0.1962(14) 0.067(8) Uiso 1 1 d
H12 H 0.772(4) -0.105(4) 0.0501(19) 0.107(11) Uiso 1 1 d
H13 H 0.768(4) 0.186(4) -0.009(2) 0.112(11) Uiso 1 1 d
H14 H 0.325(5) 0.615(4) 0.416(2) 0.111(12) Uiso 1 1 d
H15 H 0.376(8) 0.677(7) 0.327(3) 0.23(3) Uiso 1 1 d
H16 H 0.522(7) 0.611(6) 0.390(3) 0.20(3) Uiso 1 1 d
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
H1 N1 H5 107(2)
H1 N1 H8 111.1(19)
H5 N1 H8 115(2)
H1 N1 H9 105(2)
H5 N1 H9 112(2)
H8 N1 H9 107(2)
O1 C1 O4 124.6(2)
O1 C1 C6 118.1(2)
O4 C1 C6 117.3(2)
C5 C2 C4 118.9(2)
C5 C2 H7 118.3(13)
C4 C2 H7 122.8(13)
O2 C3 O3 124.8(2)
O2 C3 C4 117.9(2)
O3 C3 C4 117.3(2)
H4 N2 H14 115(3)
H4 N2 H15 115(3)
H14 N2 H15 103(3)
H4 N2 H16 111(3)
H14 N2 H16 101(3)
H15 N2 H16 111(4)
C8 C4 C2 118.9(2)
C8 C4 C3 120.8(2)
C2 C4 C3 120.27(19)
O6 N3 O5 123.4(2)
O6 N3 C5 118.2(2)
O5 N3 C5 118.4(2)
C9 C5 C2 122.2(2)
C9 C5 N3 119.5(2)
C2 C5 N3 118.3(2)
C7 C6 C10 118.8(2)
C7 C6 C1 120.2(2)
C10 C6 C1 121.0(2)
C15 C7 C6 119.3(2)
C15 C7 H2 117.0(13)
C6 C7 H2 123.7(13)
C12 C8 C4 121.3(3)
C12 C8 H3 118.8(14)
C4 C8 H3 119.9(14)
C13 C15 C7 122.4(2)
C13 C15 N4 119.5(2)
C7 C15 N4 118.1(2)
C12 C9 C5 118.4(2)
C12 C9 H10 123.2(13)
C5 C9 H10 118.2(13)
C6 C10 C14 120.4(3)
C6 C10 H11 118.2(14)
C14 C10 H11 121.4(14)
C9 C12 C8 120.2(2)
C9 C12 H6 119.5(15)
C8 C12 H6 120.2(15)
O8 N4 O7 123.1(3)
O8 N4 C15 118.5(2)
O7 N4 C15 118.5(3)
C14 C13 C15 118.5(3)
C14 C13 H13 121.0(19)
C15 C13 H13 120.5(19)
C13 C14 C10 120.6(3)
C13 C14 H12 120.9(18)
C10 C14 H12 118.5(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.250(3)
O2 C3 1.238(3)
O3 C3 1.263(2)
O4 C1 1.251(2)
N1 H1 0.92(2)
N1 H5 0.99(3)
N1 H8 0.98(3)
N1 H9 1.04(3)
C1 C6 1.508(3)
C2 C5 1.378(3)
C2 C4 1.383(3)
C2 H7 0.93(2)
C3 C4 1.515(3)
N2 H4 0.85(3)
N2 H14 0.91(4)
N2 H15 0.97(5)
N2 H16 0.90(5)
C4 C8 1.377(3)
N3 O6 1.214(2)
N3 O5 1.215(2)
N3 C5 1.464(3)
C5 C9 1.375(3)
C6 C7 1.372(3)
C6 C10 1.375(3)
C7 C15 1.368(3)
C7 H2 0.97(2)
C8 C12 1.376(3)
C8 H3 0.91(2)
C15 C13 1.359(4)
C15 N4 1.462(3)
C9 C12 1.369(4)
C9 H10 0.95(2)
C10 C14 1.382(4)
C10 H11 0.99(2)
C12 H6 0.96(2)
N4 O8 1.204(3)
N4 O7 1.208(3)
C13 C14 1.352(4)
C13 H13 0.95(3)
C14 H12 0.96(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146792
