#------------------------------------------------------------------------------
#$Date: 2025-08-21 02:19:08 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301842 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/53/4505334.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4505334
loop_
_publ_author_name
'Banerjee, Subarna'
'Murugavel, Ramaswamy'
_publ_section_title
;
 Formation of One-Dimensional Water Inside an Organic Solid: 
 Supramolecular Architectures Derived by the Interaction of Aminobenzoic
 Acids with Nitrogen Bases and H2SO4†
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              545
_journal_paper_doi               10.1021/cg034229c
_journal_volume                  4
_journal_year                    2004
_chemical_formula_moiety         'C12 H13 N3 O2'
_chemical_formula_sum            'C12 H13 N3 O2'
_chemical_formula_weight         231.25
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.932(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6455(5)
_cell_length_b                   10.9229(7)
_cell_length_c                   11.9761(15)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.15
_cell_measurement_theta_min      11.27
_cell_volume                     1162.04(18)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2149
_diffrn_reflns_theta_full        24.95
_diffrn_reflns_theta_max         24.95
_diffrn_reflns_theta_min         2.29
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.093
_exptl_crystal_colour            'deep brown'
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2044
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0363
_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)+(0.0619P)²+0.1386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1093
_reflns_number_gt                1521
_reflns_number_total             2044
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg034229csi20031125_124010.cif
_cod_data_source_block           rm079a_(Compound_1)
_cod_original_cell_volume        1162.04(17)
_cod_database_code               4505334
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_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
C1 C 0.20611(17) -0.08602(14) 0.56034(13) 0.0434(4) Uani 1 1 d
C2 C 0.28811(16) 0.02338(13) 0.63327(12) 0.0401(4) Uani 1 1 d
C3 C 0.38342(17) 0.09075(14) 0.59441(13) 0.0424(4) Uani 1 1 d
C4 C 0.46184(16) 0.19230(14) 0.65923(14) 0.0444(4) Uani 1 1 d
C5 C 0.44335(19) 0.22410(17) 0.76556(16) 0.0536(4) Uani 1 1 d
C6 C 0.3502(2) 0.15698(18) 0.80463(16) 0.0588(5) Uani 1 1 d
C7 C 0.2704(2) 0.05764(16) 0.73889(14) 0.0501(4) Uani 1 1 d
C8 C 0.03940(17) 0.34745(15) 0.66535(14) 0.0461(4) Uani 1 1 d
C9 C 0.1265(2) 0.44670(17) 0.73076(18) 0.0604(5) Uani 1 1 d
C10 C 0.2183(2) 0.5064(2) 0.6871(2) 0.0739(6) Uani 1 1 d
C11 C 0.2289(2) 0.4703(2) 0.5784(2) 0.0716(6) Uani 1 1 d
C12 C 0.1444(2) 0.37490(17) 0.51779(18) 0.0584(5) Uani 1 1 d
N1 N 0.55350(18) 0.26095(17) 0.61804(17) 0.0630(4) Uani 1 1 d
N2 N 0.05223(15) 0.31511(13) 0.56055(12) 0.0466(4) Uani 1 1 d
N3 N -0.05418(18) 0.28448(16) 0.70035(15) 0.0583(4) Uani 1 1 d
O1 O 0.23623(14) -0.11756(11) 0.47200(10) 0.0587(4) Uani 1 1 d
O2 O 0.11162(14) -0.14054(11) 0.59202(10) 0.0611(4) Uani 1 1 d
H1A H 0.611(3) 0.321(2) 0.670(2) 0.102(8) Uiso 1 1 d
H1B H 0.593(2) 0.2234(19) 0.573(2) 0.074(6) Uiso 1 1 d
H2 H -0.007(2) 0.2484(19) 0.514(2) 0.071(6) Uiso 1 1 d
H3 H 0.3950(18) 0.0664(15) 0.5230(16) 0.053(5) Uiso 1 1 d
H3A H -0.075(2) 0.3121(19) 0.762(2) 0.076(6) Uiso 1 1 d
H3B H -0.116(2) 0.2234(19) 0.6467(19) 0.072(6) Uiso 1 1 d
H5 H 0.500(2) 0.2961(17) 0.8123(17) 0.067(5) Uiso 1 1 d
H6 H 0.338(2) 0.1799(18) 0.879(2) 0.081(6) Uiso 1 1 d
H7 H 0.203(2) 0.0107(16) 0.7645(16) 0.056(5) Uiso 1 1 d
H9 H 0.118(2) 0.4697(19) 0.807(2) 0.082(6) Uiso 1 1 d
H10 H 0.280(3) 0.573(2) 0.737(2) 0.086(6) Uiso 1 1 d
H11 H 0.296(2) 0.510(2) 0.5499(18) 0.079(6) Uiso 1 1 d
H12 H 0.147(2) 0.3420(17) 0.4439(18) 0.062(5) 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
O1 C1 O2 123.83(14)
O1 C1 C2 117.76(13)
O2 C1 C2 118.41(12)
C3 C2 C7 119.51(14)
C3 C2 C1 119.38(13)
C7 C2 C1 121.11(13)
C2 C3 C4 121.32(14)
N1 C4 C3 120.92(15)
N1 C4 C5 120.99(16)
C3 C4 C5 118.08(15)
C6 C5 C4 120.66(16)
C5 C6 C7 121.08(15)
C6 C7 C2 119.33(15)
N3 C8 N2 118.46(15)
N3 C8 C9 123.76(16)
N2 C8 C9 117.77(16)
C10 C9 C8 119.51(18)
C9 C10 C11 121.16(19)
C12 C11 C10 118.05(19)
C11 C12 N2 121.17(18)
C12 N2 C8 122.34(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.2499(17)
C1 O2 1.2643(18)
C1 C2 1.509(2)
C2 C3 1.392(2)
C2 C7 1.392(2)
C3 C4 1.396(2)
C4 N1 1.388(2)
C4 C5 1.397(2)
C5 C6 1.375(3)
C6 C7 1.385(2)
C8 N3 1.326(2)
C8 N2 1.355(2)
C8 C9 1.408(2)
C9 C10 1.358(3)
C10 C11 1.401(3)
C11 C12 1.347(3)
C12 N2 1.354(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145794
