#------------------------------------------------------------------------------
#$Date: 2025-08-19 08:12:48 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301798 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/74/2017437.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_2017437
loop_
_publ_author_name
'Titi, Hatem M.'
'Goldberg, Israel'
_publ_section_title
;
 Hydrogen bonding and π--π interactions in
 1-benzofuran-2,3-dicarboxylic acid and its 1:1 cocrystals with
 pyridine, phenazine and 1,4-phenylenediamine
;
_journal_coeditor_code           GD3317
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o639
_journal_page_last               o644
_journal_paper_doi               10.1107/S0108270109047519
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H9 N2 + , C10 H5 O5 -'
_chemical_formula_moiety         'C12 H9 N2 + , C10 H5 O5 -'
_chemical_formula_sum            'C22 H14 N2 O5'
_chemical_formula_weight         386.35
_chemical_name_systematic
;
Phenazinium 3-carboxylato-1-benzofuran-2-carboxylic acid
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 1'
_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                 90.3794(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.3881(2)
_cell_length_b                   8.3227(4)
_cell_length_c                   18.6514(11)
_cell_measurement_reflns_used    2631
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.83
_cell_measurement_theta_min      2.32
_cell_volume                     836.38(7)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 12.8
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       '1 deg. φ and ω 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  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0758
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7323
_diffrn_reflns_theta_full        27.83
_diffrn_reflns_theta_max         27.83
_diffrn_reflns_theta_min         3.28
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.214
_refine_ls_extinction_coef       0.014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         1970
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0543P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.1051
_reflns_number_gt                1352
_reflns_number_total             1970
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3317.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'P n'
_cod_database_code               2017437
_cod_database_fobs_code          2017437
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, 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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 -0.0823(4) 0.0534(3) 0.33621(13) 0.0288(6) Uani d . 1 . .
C C2 0.0873(6) 0.1450(4) 0.37378(18) 0.0267(8) Uani d . 1 . .
C C3 0.2624(6) 0.2099(4) 0.32969(19) 0.0255(8) Uani d . 1 . .
C C4 0.2029(6) 0.1535(4) 0.25793(18) 0.0244(8) Uani d . 1 . .
C C5 0.3084(6) 0.1660(4) 0.18949(18) 0.0272(8) Uani d . 1 . .
H H5 0.4541 0.2280 0.1821 0.033 Uiso calc R 1 . .
C C6 0.1955(6) 0.0862(4) 0.13342(19) 0.0291(8) Uani d . 1 . .
H H6 0.2662 0.0924 0.0870 0.035 Uiso calc R 1 . .
C C7 -0.0216(6) -0.0040(5) 0.14333(18) 0.0323(9) Uani d . 1 . .
H H7 -0.0965 -0.0555 0.1032 0.039 Uiso calc R 1 . .
C C8 -0.1290(6) -0.0196(5) 0.21002(18) 0.0287(8) Uani d . 1 . .
H H8 -0.2757 -0.0805 0.2174 0.034 Uiso calc R 1 . .
C C9 -0.0080(6) 0.0599(4) 0.26538(18) 0.0258(8) Uani d . 1 . .
C C10 0.0409(7) 0.1437(5) 0.45215(19) 0.0306(9) Uani d . 1 . .
O O11 0.1996(5) 0.2263(3) 0.49206(14) 0.0373(7) Uani d . 1 . .
H H11 0.312(8) 0.288(6) 0.461(2) 0.045 Uiso d . 1 . .
O O12 -0.1297(4) 0.0690(3) 0.47726(13) 0.0383(7) Uani d . 1 . .
C C13 0.4685(6) 0.3198(4) 0.3483(2) 0.0290(8) Uani d . 1 . .
O O14 0.5928(4) 0.3723(3) 0.29539(13) 0.0324(6) Uani d . 1 . .
O O15 0.5115(4) 0.3595(3) 0.41287(13) 0.0351(7) Uani d . 1 . .
C C16 0.9288(6) 0.4975(5) 0.16645(19) 0.0309(9) Uani d . 1 . .
H H16 0.7843 0.4349 0.1746 0.037 Uiso calc R 1 . .
C C17 1.0186(7) 0.5167(5) 0.09880(19) 0.0330(9) Uani d . 1 . .
H H17 0.9324 0.4690 0.0596 0.040 Uiso calc R 1 . .
C C18 1.2367(7) 0.6057(5) 0.0857(2) 0.0336(9) Uani d . 1 . .
H H18 1.2961 0.6159 0.0380 0.040 Uiso calc R 1 . .
C C19 1.3626(6) 0.6769(4) 0.14050(19) 0.0301(8) Uani d . 1 . .
H H19 1.5097 0.7360 0.1310 0.036 Uiso calc R 1 . .
C C20 1.2749(6) 0.6632(4) 0.21200(19) 0.0259(8) Uani d . 1 . .
N N21 1.3953(5) 0.7381(4) 0.26556(16) 0.0277(7) Uani d . 1 . .
C C22 1.3032(6) 0.7270(4) 0.3321(2) 0.0274(8) Uani d . 1 . .
C C23 1.4220(6) 0.8082(5) 0.38998(19) 0.0290(8) Uani d . 1 . .
H H23 1.5665 0.8707 0.3818 0.035 Uiso calc R 1 . .
C C24 1.3275(6) 0.7959(5) 0.4571(2) 0.0325(9) Uani d . 1 . .
H H24 1.4084 0.8494 0.4957 0.039 Uiso calc R 1 . .
C C25 1.1094(7) 0.7041(5) 0.4708(2) 0.0329(9) Uani d . 1 . .
H H25 1.0456 0.6993 0.5181 0.039 Uiso calc R 1 . .
C C26 0.9915(6) 0.6236(5) 0.41720(19) 0.0295(8) Uani d . 1 . .
H H26 0.8491 0.5604 0.4271 0.035 Uiso calc R 1 . .
C C27 1.0827(6) 0.6349(4) 0.34679(19) 0.0260(8) Uani d . 1 . .
N N28 0.9682(5) 0.5593(4) 0.29184(15) 0.0266(7) Uani d . 1 . .
H H28 0.815(7) 0.492(5) 0.3054(19) 0.032 Uiso d . 1 . .
C C29 1.0546(6) 0.5726(4) 0.22423(19) 0.0255(8) Uani 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
C2 O1 C9 . . 105.6(3) ?
C3 C2 O1 . . 111.8(3) ?
C3 C2 C10 . . 135.8(3) ?
O1 C2 C10 . . 112.4(3) ?
C2 C3 C4 . . 106.1(3) ?
C2 C3 C13 . . 128.6(3) ?
C4 C3 C13 . . 125.2(3) ?
C9 C4 C5 . . 118.0(3) ?
C9 C4 C3 . . 105.4(3) ?
C5 C4 C3 . . 136.5(3) ?
C6 C5 C4 . . 118.3(3) ?
C6 C5 H5 . . 120.8 ?
C4 C5 H5 . . 120.8 ?
C5 C6 C7 . . 121.5(3) ?
C5 C6 H6 . . 119.2 ?
C7 C6 H6 . . 119.2 ?
C8 C7 C6 . . 121.6(3) ?
C8 C7 H7 . . 119.2 ?
C6 C7 H7 . . 119.2 ?
C7 C8 C9 . . 115.4(3) ?
C7 C8 H8 . . 122.3 ?
C9 C8 H8 . . 122.3 ?
O1 C9 C8 . . 123.7(3) ?
O1 C9 C4 . . 111.1(3) ?
C8 C9 C4 . . 125.2(3) ?
O12 C10 O11 . . 122.7(3) ?
O12 C10 C2 . . 121.3(3) ?
O11 C10 C2 . . 116.0(3) ?
C10 O11 H11 . . 110(2) ?
O15 C13 O14 . . 123.6(3) ?
O15 C13 C3 . . 121.0(3) ?
O14 C13 C3 . . 115.4(3) ?
C17 C16 C29 . . 118.8(3) ?
C17 C16 H16 . . 120.6 ?
C29 C16 H16 . . 120.6 ?
C16 C17 C18 . . 121.5(3) ?
C16 C17 H17 . . 119.2 ?
C18 C17 H17 . . 119.2 ?
C19 C18 C17 . . 120.7(3) ?
C19 C18 H18 . . 119.7 ?
C17 C18 H18 . . 119.7 ?
C18 C19 C20 . . 120.2(3) ?
C18 C19 H19 . . 119.9 ?
C20 C19 H19 . . 119.9 ?
N21 C20 C19 . . 119.9(3) ?
N21 C20 C29 . . 121.7(3) ?
C19 C20 C29 . . 118.3(3) ?
C22 N21 C20 . . 118.5(3) ?
N21 C22 C23 . . 120.1(3) ?
N21 C22 C27 . . 121.5(3) ?
C23 C22 C27 . . 118.4(3) ?
C24 C23 C22 . . 119.6(3) ?
C24 C23 H23 . . 120.2 ?
C22 C23 H23 . . 120.2 ?
C23 C24 C25 . . 121.3(4) ?
C23 C24 H24 . . 119.4 ?
C25 C24 H24 . . 119.4 ?
C26 C25 C24 . . 121.0(4) ?
C26 C25 H25 . . 119.5 ?
C24 C25 H25 . . 119.5 ?
C25 C26 C27 . . 119.3(3) ?
C25 C26 H26 . . 120.3 ?
C27 C26 H26 . . 120.3 ?
N28 C27 C26 . . 121.1(3) ?
N28 C27 C22 . . 118.5(3) ?
C26 C27 C22 . . 120.4(3) ?
C27 N28 C29 . . 120.8(3) ?
C27 N28 H28 . . 115(2) ?
C29 N28 H28 . . 124(2) ?
N28 C29 C16 . . 120.5(3) ?
N28 C29 C20 . . 119.0(3) ?
C16 C29 C20 . . 120.5(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
O1 C2 . 1.378(4) ?
O1 C9 . 1.384(4) ?
C2 C3 . 1.367(5) ?
C2 C10 . 1.484(5) ?
C3 C4 . 1.452(5) ?
C3 C13 . 1.478(5) ?
C4 C9 . 1.385(5) ?
C4 C5 . 1.405(5) ?
C5 C6 . 1.377(5) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.403(5) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.381(5) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.385(5) ?
C8 H8 . 0.9500 ?
C10 O12 . 1.207(4) ?
C10 O11 . 1.323(4) ?
O11 H11 . 0.99(5) ?
C13 O15 . 1.269(4) ?
C13 O14 . 1.273(4) ?
C16 C17 . 1.364(5) ?
C16 C29 . 1.415(5) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.412(5) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.359(5) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.422(5) ?
C19 H19 . 0.9500 ?
C20 N21 . 1.341(4) ?
C20 C29 . 1.426(5) ?
N21 C22 . 1.343(4) ?
C22 C23 . 1.422(5) ?
C22 C27 . 1.442(5) ?
C23 C24 . 1.359(5) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.426(6) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.357(5) ?
C25 H25 . 0.9500 ?
C26 C27 . 1.408(5) ?
C26 H26 . 0.9500 ?
C27 N28 . 1.349(4) ?
N28 C29 . 1.351(4) ?
N28 H28 . 1.03(4) ?
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
O11 H11 O15 . 0.99(5) 1.52(5) 2.503(3) 171(4)
N28 H28 O14 . 1.03(4) 1.57(4) 2.553(4) 158(3)
C6 H6 O12 2_554 0.95 2.51 3.328(4) 143.7
C8 H8 N21 1_345 0.95 2.50 3.427(4) 165.3
C26 H26 O15 . 0.95 2.48 3.395(4) 160.8
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654202
2 PubChem 139060811
