#------------------------------------------------------------------------------
#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/47/7204797.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_7204797
loop_
_publ_author_name
'Christer B. Aakeröy'
'John Desper'
'Brian A. Helfrich'
_publ_section_title
;
 Heteromeric intermolecular interactions as synthetic tools for the
 formation of binary co-crystals
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              19
_journal_page_last               24
_journal_paper_doi               10.1039/b315181f
_journal_volume                  6
_journal_year                    2004
_chemical_formula_moiety
;
(C6 H6 N2 O) (C7 H5 F O2)
;
_chemical_formula_sum            'C13 H11 F N2 O3'
_chemical_formula_weight         262.24
_chemical_melting_point          154.0(10)
_chemical_name_common            'isonicotinamide, 4-fluorobenzoic acid'
_chemical_name_systematic
;
isonicotinamide, 4-fluorobenzoic acid
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 95.402(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.725(13)
_cell_length_b                   5.231(3)
_cell_length_c                   20.785(12)
_cell_measurement_reflns_used    617
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      23.45
_cell_measurement_theta_min      2.75
_cell_volume                     2460(2)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '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  0.1491
_diffrn_reflns_av_sigmaI/netI    0.1586
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8008
_diffrn_reflns_theta_full        26.55
_diffrn_reflns_theta_max         26.55
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       0.0119(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.868
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2520
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.868
_refine_ls_R_factor_all          0.1392
_refine_ls_R_factor_gt           0.0604
_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)+(0.0700P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1269
_refine_ls_wR_factor_ref         0.1624
_reflns_number_gt                1070
_reflns_number_total             2520
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b315181f.txt
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/adriana/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '153-155' was changed to '154.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7204797
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.39043(11) 0.4010(4) 0.32302(11) 0.0490(6) Uani 1 1 d . . .
C2 C 0.43565(13) 0.2686(5) 0.30379(14) 0.0541(8) Uani 1 1 d . . .
H2 H 0.4495 0.3117 0.2640 0.065 Uiso 1 1 calc R . .
C3 C 0.46327(14) 0.0722(5) 0.33891(12) 0.0527(8) Uani 1 1 d . . .
H3 H 0.4948 -0.0169 0.3230 0.063 Uiso 1 1 calc R . .
C4 C 0.44405(11) 0.0079(4) 0.39776(11) 0.0399(7) Uani 1 1 d . . .
C5 C 0.39709(13) 0.1444(5) 0.41818(13) 0.0494(8) Uani 1 1 d . . .
H5 H 0.3825 0.1061 0.4579 0.059 Uiso 1 1 calc R . .
C6 C 0.37183(13) 0.3375(6) 0.37959(13) 0.0542(8) Uani 1 1 d . . .
H6 H 0.3399 0.4285 0.3940 0.065 Uiso 1 1 calc R . .
O7 O 0.44724(9) -0.2485(3) 0.49165(9) 0.0564(6) Uani 1 1 d . . .
N7 N 0.51467(11) -0.3353(4) 0.42204(11) 0.0474(7) Uani 1 1 d . . .
H71 H 0.5275(12) -0.467(5) 0.4479(12) 0.057 Uiso 1 1 d . . .
H72 H 0.5332(13) -0.298(5) 0.3849(13) 0.057 Uiso 1 1 d . . .
C7 C 0.46949(12) -0.2029(5) 0.44093(13) 0.0411(7) Uani 1 1 d . . .
C11 C 0.33613(12) 1.0376(5) 0.16165(12) 0.0434(7) Uani 1 1 d . . .
C12 C 0.35880(14) 1.1224(6) 0.10610(13) 0.0572(8) Uani 1 1 d . . .
H12 H 0.3939 1.0505 0.0936 0.069 Uiso 1 1 calc R . .
C13 C 0.33044(15) 1.3116(6) 0.06879(15) 0.0688(10) Uani 1 1 d . . .
H13 H 0.3455 1.3691 0.0307 0.083 Uiso 1 1 calc R . .
F14 F 0.25160(9) 1.5990(4) 0.05223(9) 0.0960(8) Uani 1 1 d . . .
C14 C 0.28012(15) 1.4122(6) 0.08868(14) 0.0591(9) Uani 1 1 d . . .
C15 C 0.25622(14) 1.3355(6) 0.14330(14) 0.0616(9) Uani 1 1 d . . .
H15 H 0.2213 1.4097 0.1555 0.074 Uiso 1 1 calc R . .
C16 C 0.28503(13) 1.1454(5) 0.18005(14) 0.0518(8) Uani 1 1 d . . .
H16 H 0.2696 1.0891 0.2180 0.062 Uiso 1 1 calc R . .
O17 O 0.34021(9) 0.7646(4) 0.25167(9) 0.0575(6) Uani 1 1 d . . .
H17 H 0.3626(13) 0.619(5) 0.2778(13) 0.069 Uiso 1 1 d . . .
C17 C 0.36761(13) 0.8342(5) 0.20143(13) 0.0443(7) Uani 1 1 d . . .
O18 O 0.41438(9) 0.7391(3) 0.18904(9) 0.0573(6) Uani 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'
F F 0.0171 0.0103 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C2 117.0(2) . . ?
N1 C2 C3 123.7(3) . . ?
N1 C2 H2 118.1 . . ?
C3 C2 H2 118.1 . . ?
C2 C3 C4 119.0(3) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 117.7(3) . . ?
C3 C4 C7 124.9(2) . . ?
C5 C4 C7 117.4(2) . . ?
C6 C5 C4 119.3(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
N1 C6 C5 123.2(3) . . ?
N1 C6 H6 118.4 . . ?
C5 C6 H6 118.4 . . ?
C7 N7 H71 116.0(17) . . ?
C7 N7 H72 123.9(17) . . ?
H71 N7 H72 120(2) . . ?
O7 C7 N7 122.8(3) . . ?
O7 C7 C4 119.1(2) . . ?
N7 C7 C4 118.1(2) . . ?
C16 C11 C12 119.4(3) . . ?
C16 C11 C17 120.8(2) . . ?
C12 C11 C17 119.8(3) . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 118.0(3) . . ?
C14 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
C13 C14 F14 118.6(3) . . ?
C13 C14 C15 123.5(3) . . ?
F14 C14 C15 117.9(3) . . ?
C14 C15 C16 117.8(3) . . ?
C14 C15 H15 121.1 . . ?
C16 C15 H15 121.1 . . ?
C11 C16 C15 120.6(3) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C17 O17 H17 111.8(16) . . ?
O18 C17 O17 122.7(3) . . ?
O18 C17 C11 123.8(2) . . ?
O17 C17 C11 113.6(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.328(3) . ?
N1 C2 1.332(3) . ?
C2 C3 1.377(4) . ?
C2 H2 0.9400 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.384(4) . ?
C4 C7 1.502(3) . ?
C5 C6 1.381(4) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
O7 C7 1.235(3) . ?
N7 C7 1.328(3) . ?
N7 H71 0.91(2) . ?
N7 H72 0.93(3) . ?
C11 C16 1.377(4) . ?
C11 C12 1.381(4) . ?
C11 C17 1.489(4) . ?
C12 C13 1.379(4) . ?
C12 H12 0.9400 . ?
C13 C14 1.358(4) . ?
C13 H13 0.9400 . ?
F14 C14 1.362(3) . ?
C14 C15 1.364(4) . ?
C15 C16 1.381(4) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?
O17 C17 1.317(3) . ?
O17 H17 1.04(3) . ?
C17 O18 1.223(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O17 H17 N1 1.04(3) 1.57(3) 2.608(3) 173(3) .
N7 H72 O18 0.93(3) 2.04(3) 2.964(3) 170(2) 2_645
C3 H3 O18 0.94 2.46 3.378(4) 165.3 2_645
N7 H71 O7 0.91(2) 2.00(3) 2.901(3) 177(2) 5_646
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 0.4(4) . . . . ?
N1 C2 C3 C4 -0.7(5) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C2 C3 C4 C7 179.4(2) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C7 C4 C5 C6 -179.1(2) . . . . ?
C2 N1 C6 C5 0.1(4) . . . . ?
C4 C5 C6 N1 -0.1(4) . . . . ?
C3 C4 C7 O7 -177.5(3) . . . . ?
C5 C4 C7 O7 1.2(4) . . . . ?
C3 C4 C7 N7 1.4(4) . . . . ?
C5 C4 C7 N7 -179.9(3) . . . . ?
C16 C11 C12 C13 -0.6(5) . . . . ?
C17 C11 C12 C13 -179.7(3) . . . . ?
C11 C12 C13 C14 0.5(5) . . . . ?
C12 C13 C14 F14 -179.9(3) . . . . ?
C12 C13 C14 C15 -0.2(5) . . . . ?
C13 C14 C15 C16 0.0(5) . . . . ?
F14 C14 C15 C16 179.7(3) . . . . ?
C12 C11 C16 C15 0.4(5) . . . . ?
C17 C11 C16 C15 179.5(3) . . . . ?
C14 C15 C16 C11 -0.2(5) . . . . ?
C16 C11 C17 O18 -176.8(3) . . . . ?
C12 C11 C17 O18 2.2(4) . . . . ?
C16 C11 C17 O17 3.3(4) . . . . ?
C12 C11 C17 O17 -177.6(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21149527
2 PubChem 85991834
