#------------------------------------------------------------------------------
#$Date: 2024-07-09 05:03:39 +0300 (Tue, 09 Jul 2024) $
#$Revision: 293326 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/25/2312544.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_2312544
loop_
_publ_author_name
'Sánchez-Pacheco, Addi Dana'
'Huerta, Eduardo H.'
'Espinosa-Camargo, Josué Benjamín'
'Rodríguez-Nájera, Evelyn Valeria'
'Martínez-Otero, Diego'
'Hernández-Ortega, Simón'
'Valdés-Martínez, Jesús'
_publ_section_title
;
 Using cocrystals as a tool to study non-crystallizing molecules: crystal
 structure, Hirshfeld surface analysis and computational study of the 1:1
 cocrystal of (E)-N-(3,4-difluorophenyl)-1-(pyridin-4-yl)methanimine and
 acetic acid.
;
_journal_coeditor_code           DG3053
_journal_issue                   8
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_paper_doi               10.1107/S2053229624005187
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C12 H8 F2 N2, C2 H4 O2'
_chemical_formula_moiety         'C12 H8 F2 N2, C2 H4 O2'
_chemical_formula_sum            'C14 H12 F2 N2 O2'
_chemical_formula_weight         278.26
_chemical_name_systematic
;
(E)-N-(3,4-difluorophenyl)-1-(pyridin-4-yl)methanimine; acetic
acid
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                79.5350(10)
_cell_angle_beta                 89.2230(10)
_cell_angle_gamma                82.8800(10)
_cell_formula_units_Z            2
_cell_length_a                   3.80470(10)
_cell_length_b                   11.0101(4)
_cell_length_c                   15.4968(6)
_cell_measurement_reflns_used    8212
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.51
_cell_volume                     633.42(4)
_computing_cell_refinement
;
SAINT (Bruker, 1998)
;
_computing_data_collection
;
APEX2 (Bruker, 2005)
;
_computing_data_reduction
;
SAINT (Bruker, 1998)
;
_computing_molecular_graphics
;
X-Seed 4 (Barbour, 2020)
;
_computing_publication_material
;
CIFTAB (Sheldrick, 2008) and PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11642
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.516
_diffrn_reflns_theta_min         1.336
_diffrn_source                   'Incoatec ImuS'
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_description       Prism
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.349
_exptl_crystal_size_mid          0.281
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.277
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2896
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0586P)²+0.0912P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1096
_reflns_number_gt                2531
_reflns_number_total             2896
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dg3053.cif
_cod_data_source_block           I
_cod_database_code               2312544
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.960
_shelx_estimated_absorpt_t_max   0.976
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 1.2872(2) 0.35402(6) 0.05185(4) 0.0267(2) Uani d 1 . .
F F2 1.3162(2) 0.14057(7) -0.00933(4) 0.0270(2) Uani d 1 . .
O O1 1.0367(2) 0.26535(7) 0.77019(5) 0.0227(2) Uani d 1 . .
H H1 1.149(4) 0.2625(16) 0.7221(8) 0.034 Uiso d 1 . .
O O2 0.9139(2) 0.46992(8) 0.71996(5) 0.0248(2) Uani d 1 . .
N N1 0.3443(2) 0.25072(9) 0.61506(6) 0.0173(2) Uani d 1 . .
N N2 0.8633(2) 0.15059(9) 0.33060(6) 0.0160(2) Uani d 1 . .
C C2 0.2908(3) 0.35258(10) 0.55249(7) 0.0184(2) Uani d 1 . .
H H2 0.170570 0.426595 0.567636 0.022 Uiso calc 1 . .
C C3 0.4024(3) 0.35531(10) 0.46656(7) 0.0179(2) Uani d 1 . .
H H3 0.356878 0.429362 0.423999 0.022 Uiso calc 1 . .
C C4 0.5820(3) 0.24782(10) 0.44380(7) 0.0146(2) Uani d 1 . .
C C5 0.6392(3) 0.14168(10) 0.50878(7) 0.0165(2) Uani d 1 . .
H H5 0.760800 0.066575 0.495690 0.020 Uiso calc 1 . .
C C6 0.5164(3) 0.14717(11) 0.59270(7) 0.0186(2) Uani d 1 . .
H H6 0.555773 0.074234 0.636467 0.022 Uiso calc 1 . .
C C7 0.7017(3) 0.24845(10) 0.35283(7) 0.0162(2) Uani d 1 . .
H H7 0.657799 0.322648 0.310346 0.019 Uiso calc 1 . .
C C8 0.9763(3) 0.15414(10) 0.24265(7) 0.0150(2) Uani d 1 . .
C C9 1.0735(3) 0.26135(10) 0.18881(7) 0.0165(2) Uani d 1 . .
H H9 1.062252 0.337691 0.209691 0.020 Uiso calc 1 . .
C C10 1.1855(3) 0.25322(11) 0.10491(7) 0.0180(2) Uani d 1 . .
C C11 1.2023(3) 0.14296(11) 0.07350(7) 0.0188(2) Uani d 1 . .
C C12 1.1089(3) 0.03675(11) 0.12571(7) 0.0195(2) Uani d 1 . .
H H12 1.118976 -0.038866 0.103919 0.023 Uiso calc 1 . .
C C13 0.9997(3) 0.04275(10) 0.21085(7) 0.0175(2) Uani d 1 . .
H H13 0.939981 -0.030190 0.248056 0.021 Uiso calc 1 . .
C C14 0.8935(3) 0.37915(10) 0.77688(7) 0.0173(2) Uani d 1 . .
C C15 0.7135(3) 0.38455(11) 0.86306(8) 0.0218(3) Uani d 1 . .
H H15A 0.891114 0.385338 0.908111 0.026 Uiso calc 1 . .
H H15B 0.587614 0.311498 0.879896 0.026 Uiso calc 1 . .
H H15C 0.544320 0.460336 0.857478 0.026 Uiso calc 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C14 O1 H1 . . 113.1(11) ?
C2 N1 C6 . . 117.64(9) ?
C7 N2 C8 . . 119.44(9) yes
N1 C2 C3 . . 123.21(10) ?
N1 C2 H2 . . 118.4 ?
C3 C2 H2 . . 118.4 ?
C2 C3 C4 . . 118.93(10) ?
C2 C3 H3 . . 120.5 ?
C4 C3 H3 . . 120.5 ?
C3 C4 C5 . . 118.06(10) ?
C3 C4 C7 . . 119.85(10) ?
C5 C4 C7 . . 122.09(10) ?
C6 C5 C4 . . 119.10(10) ?
C6 C5 H5 . . 120.4 ?
C4 C5 H5 . . 120.4 ?
N1 C6 C5 . . 123.06(10) ?
N1 C6 H6 . . 118.5 ?
C5 C6 H6 . . 118.5 ?
N2 C7 C4 . . 120.72(10) yes
N2 C7 H7 . . 119.6 ?
C4 C7 H7 . . 119.6 ?
C13 C8 C9 . . 119.71(10) ?
C13 C8 N2 . . 116.81(10) ?
C9 C8 N2 . . 123.45(10) ?
C10 C9 C8 . . 118.37(10) ?
C10 C9 H9 . . 120.8 ?
C8 C9 H9 . . 120.8 ?
F1 C10 C9 . . 119.95(10) ?
F1 C10 C11 . . 118.55(10) ?
C9 C10 C11 . . 121.49(10) ?
F2 C11 C12 . . 120.40(10) ?
F2 C11 C10 . . 118.78(10) ?
C12 C11 C10 . . 120.81(10) ?
C11 C12 C13 . . 118.52(10) ?
C11 C12 H12 . . 120.7 ?
C13 C12 H12 . . 120.7 ?
C12 C13 C8 . . 121.07(10) ?
C12 C13 H13 . . 119.5 ?
C8 C13 H13 . . 119.5 ?
O2 C14 O1 . . 123.43(10) yes
O2 C14 C15 . . 123.74(10) yes
O1 C14 C15 . . 112.80(9) yes
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
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
F1 C10 . 1.3504(13) ?
F2 C11 . 1.3531(12) ?
O1 C14 . 1.3243(14) yes
O1 H1 . 0.858(9) ?
O2 C14 . 1.2166(14) yes
N1 C2 . 1.3391(14) ?
N1 C6 . 1.3419(15) ?
N2 C7 . 1.2739(15) yes
N2 C8 . 1.4188(13) yes
C2 C3 . 1.3884(15) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.3917(15) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.3938(15) ?
C4 C7 . 1.4746(14) ?
C5 C6 . 1.3850(15) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 C13 . 1.3951(16) ?
C8 C9 . 1.4029(15) ?
C9 C10 . 1.3777(15) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.3818(17) ?
C11 C12 . 1.3783(16) ?
C12 C13 . 1.3884(15) ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
C14 C15 . 1.5000(15) ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
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
O1 H1 N1 1_655 0.858(9) 1.827(9) 2.6819(12) 173.6(17) yes
C2 H2 O2 1_455 0.95 2.64 3.3344(14) 130.1 yes
C3 H3 O2 2_666 0.95 2.48 3.3174(14) 147.1 yes
C9 H9 O2 2_766 0.95 2.56 3.5088(14) 173.2 yes
C13 H13 O1 2_756 0.95 2.65 3.3713(14) 133.6 yes
C15 H15B F2 1_456 0.98 2.61 3.5224(14) 154.9 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C2 C3 . . . . 0.39(17) ?
N1 C2 C3 C4 . . . . -0.65(17) ?
C2 C3 C4 C5 . . . . 0.43(16) ?
C2 C3 C4 C7 . . . . 179.76(10) ?
C3 C4 C5 C6 . . . . 0.00(16) ?
C7 C4 C5 C6 . . . . -179.31(10) ?
C2 N1 C6 C5 . . . . 0.08(17) ?
C4 C5 C6 N1 . . . . -0.27(17) ?
C8 N2 C7 C4 . . . . -179.80(9) ?
C3 C4 C7 N2 . . . . -179.29(10) yes
C5 C4 C7 N2 . . . . 0.01(17) yes
C7 N2 C8 C13 . . . . -151.63(11) yes
C7 N2 C8 C9 . . . . 30.40(16) yes
C13 C8 C9 C10 . . . . 0.87(16) ?
N2 C8 C9 C10 . . . . 178.78(10) ?
C8 C9 C10 F1 . . . . -178.78(10) ?
C8 C9 C10 C11 . . . . 0.20(17) ?
F1 C10 C11 F2 . . . . -0.67(17) ?
C9 C10 C11 F2 . . . . -179.67(10) ?
F1 C10 C11 C12 . . . . 178.57(10) ?
C9 C10 C11 C12 . . . . -0.43(18) ?
F2 C11 C12 C13 . . . . 178.80(10) ?
C10 C11 C12 C13 . . . . -0.42(18) ?
C11 C12 C13 C8 . . . . 1.50(17) ?
C9 C8 C13 C12 . . . . -1.74(17) ?
N2 C8 C13 C12 . . . . -179.79(10) ?
