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#$Date: 2025-08-21 04:34:05 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301843 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/24/4512416.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_4512416
loop_
_publ_author_name
'Surov, Artem O.'
'Simagina, Anna A.'
'Manin, Nikolay G.'
'Kuzmina, Lyudmila G.'
'Churakov, Andrei V.'
'Perlovich, German L.'
_publ_section_title
;
 Fenamate Cocrystals with 4,4′-Bipyridine: Structural and
 Thermodynamic Aspects
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              228
_journal_paper_doi               10.1021/cg5012633
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         '2(C13 H9 F3 N2 O2), C10 H8 N2'
_chemical_formula_sum            'C36 H26 F6 N6 O4'
_chemical_formula_weight         720.63
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.386(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   26.000(4)
_cell_length_b                   6.7394(10)
_cell_length_c                   19.854(3)
_cell_measurement_reflns_used    2603
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.331
_cell_measurement_theta_min      2.203
_cell_volume                     3239.4(8)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_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  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13319
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.23
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.9760
_exptl_absorpt_correction_T_min  0.9702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         3523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0423
_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)+(0.0469P)²+2.4794P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1115
_reflns_number_gt                2732
_reflns_number_total             3523
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg5012633_si_004.cif
_cod_data_source_block           NFA-BP
_cod_depositor_comments
'Adding full bibliography for 4512412--4512416.cif.'
_cod_original_cell_volume        3239.3(8)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4512416
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
N1 N 0.19215(6) 0.2793(2) 0.34145(7) 0.0281(3) Uani 1 1 d
N3 N 0.10198(5) 0.23169(19) 0.26114(7) 0.0264(3) Uani 1 1 d
O1 O 0.24803(5) 0.21320(18) 0.17020(6) 0.0321(3) Uani 1 1 d
O2 O 0.27265(5) 0.23207(19) 0.28966(6) 0.0358(3) Uani 1 1 d
C11 C 0.17694(6) 0.2058(2) 0.21687(8) 0.0241(3) Uani 1 1 d
C12 C 0.15610(6) 0.2376(2) 0.27298(8) 0.0231(3) Uani 1 1 d
C13 C 0.06708(7) 0.1955(2) 0.19383(9) 0.0296(4) Uani 1 1 d
C14 C 0.08304(7) 0.1603(3) 0.13591(9) 0.0319(4) Uani 1 1 d
C15 C 0.13883(7) 0.1654(2) 0.14813(9) 0.0284(4) Uani 1 1 d
C16 C 0.23675(7) 0.2179(2) 0.22941(8) 0.0257(3) Uani 1 1 d
C21 C 0.18182(7) 0.3411(2) 0.40265(8) 0.0253(3) Uani 1 1 d
C22 C 0.13387(7) 0.2977(2) 0.41535(9) 0.0276(4) Uani 1 1 d
C23 C 0.12910(7) 0.3584(3) 0.47979(9) 0.0297(4) Uani 1 1 d
C24 C 0.17090(7) 0.4627(3) 0.53192(9) 0.0325(4) Uani 1 1 d
C25 C 0.21811(7) 0.5081(3) 0.51824(9) 0.0318(4) Uani 1 1 d
C26 C 0.22363(7) 0.4485(2) 0.45494(9) 0.0286(4) Uani 1 1 d
C27 C 0.07646(8) 0.3139(3) 0.49054(10) 0.0416(5) Uani 1 1 d
F1 F 0.03481(5) 0.4273(3) 0.44996(8) 0.0763(5) Uani 1 1 d
F2 F 0.05863(6) 0.1280(2) 0.47127(8) 0.0745(5) Uani 1 1 d
F3 F 0.07959(5) 0.3339(3) 0.55809(6) 0.0709(5) Uani 1 1 d
N2 N 0.35461(6) 0.2459(2) 0.19948(7) 0.0284(3) Uani 1 1 d
C1 C 0.37826(7) 0.2837(2) 0.15112(9) 0.0301(4) Uani 1 1 d
C2 C 0.43462(7) 0.2840(2) 0.16860(9) 0.0285(4) Uani 1 1 d
C3 C 0.46948(7) 0.2416(2) 0.23938(8) 0.0242(3) Uani 1 1 d
C4 C 0.44465(7) 0.2020(2) 0.28908(9) 0.0279(4) Uani 1 1 d
C5 C 0.38790(7) 0.2064(2) 0.26725(9) 0.0295(4) Uani 1 1 d
H11 H 0.2903(13) 0.230(4) 0.1800(15) 0.092(9) Uiso 1 1 d
H12 H 0.2272(9) 0.283(3) 0.3451(11) 0.045(6) Uiso 1 1 d
H1 H 0.3538(8) 0.313(3) 0.1006(11) 0.042(5) Uiso 1 1 d
H2 H 0.4491(8) 0.316(3) 0.1313(10) 0.035(5) Uiso 1 1 d
H4 H 0.4660(8) 0.166(3) 0.3377(10) 0.033(5) Uiso 1 1 d
H5 H 0.3694(8) 0.175(3) 0.2998(10) 0.041(5) Uiso 1 1 d
H13 H 0.0275(8) 0.191(3) 0.1876(10) 0.035(5) Uiso 1 1 d
H14 H 0.0551(8) 0.132(3) 0.0891(10) 0.042(5) Uiso 1 1 d
H15 H 0.1526(7) 0.143(3) 0.1097(10) 0.032(5) Uiso 1 1 d
H22 H 0.1046(8) 0.224(3) 0.3801(10) 0.038(5) Uiso 1 1 d
H24 H 0.1677(8) 0.502(3) 0.5768(10) 0.039(5) Uiso 1 1 d
H25 H 0.2470(8) 0.580(3) 0.5536(10) 0.037(5) Uiso 1 1 d
H26 H 0.2557(8) 0.478(3) 0.4444(9) 0.031(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'
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_3
C12 N1 C21 130.09(14) .
C12 N1 H12 113.4(13) .
C21 N1 H12 115.9(13) .
C13 N3 C12 117.88(14) .
C16 O1 H11 113.1(15) .
C15 C11 C12 117.41(15) .
C15 C11 C16 120.22(14) .
C12 C11 C16 122.37(14) .
N3 C12 N1 118.35(14) .
N3 C12 C11 122.27(14) .
N1 C12 C11 119.37(14) .
N3 C13 C14 124.40(16) .
N3 C13 H13 115.2(11) .
C14 C13 H13 120.4(11) .
C13 C14 C15 117.76(16) .
C13 C14 H14 119.2(11) .
C15 C14 H14 123.1(11) .
C14 C15 C11 120.27(15) .
C14 C15 H15 121.8(10) .
C11 C15 H15 118.0(11) .
O2 C16 O1 122.54(15) .
O2 C16 C11 123.18(14) .
O1 C16 C11 114.28(14) .
C22 C21 N1 124.28(15) .
C22 C21 C26 118.64(15) .
N1 C21 C26 117.05(15) .
C21 C22 C23 119.44(16) .
C21 C22 H22 120.0(11) .
C23 C22 H22 120.5(11) .
C24 C23 C22 121.77(16) .
C24 C23 C27 120.35(15) .
C22 C23 C27 117.84(15) .
C25 C24 C23 118.34(15) .
C25 C24 H24 120.2(11) .
C23 C24 H24 121.4(11) .
C26 C25 C24 120.66(16) .
C26 C25 H25 120.3(11) .
C24 C25 H25 119.0(11) .
C25 C26 C21 121.13(16) .
C25 C26 H26 122.1(11) .
C21 C26 H26 116.8(11) .
F3 C27 F1 106.93(17) .
F3 C27 F2 105.78(17) .
F1 C27 F2 104.09(17) .
F3 C27 C23 113.90(16) .
F1 C27 C23 112.62(16) .
F2 C27 C23 112.77(16) .
C5 N2 C1 117.51(14) .
N2 C1 C2 122.93(16) .
N2 C1 H1 118.0(12) .
C2 C1 H1 119.1(12) .
C1 C2 C3 119.60(16) .
C1 C2 H2 118.8(11) .
C3 C2 H2 121.6(11) .
C4 C3 C2 117.10(15) .
C4 C3 C3 121.58(18) 2_655
C2 C3 C3 121.31(17) 2_655
C5 C4 C3 119.64(16) .
C5 C4 H4 119.1(11) .
C3 C4 H4 121.2(11) .
N2 C5 C4 123.22(16) .
N2 C5 H5 115.0(12) .
C4 C5 H5 121.7(12) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C12 1.370(2) .
N1 C21 1.400(2) .
N1 H12 0.89(2) .
N3 C13 1.336(2) .
N3 C12 1.340(2) .
O1 C16 1.3118(19) .
O1 H11 1.05(3) .
O2 C16 1.2235(19) .
C11 C15 1.390(2) .
C11 C12 1.421(2) .
C11 C16 1.485(2) .
C13 C14 1.378(2) .
C13 H13 0.99(2) .
C14 C15 1.381(2) .
C14 H14 0.967(19) .
C15 H15 0.966(18) .
C21 C22 1.390(2) .
C21 C26 1.400(2) .
C22 C23 1.391(2) .
C22 H22 0.96(2) .
C23 C24 1.388(2) .
C23 C27 1.491(3) .
C24 C25 1.384(3) .
C24 H24 0.961(19) .
C25 C26 1.376(2) .
C25 H25 0.953(19) .
C26 H26 0.953(18) .
C27 F3 1.321(2) .
C27 F1 1.330(2) .
C27 F2 1.342(2) .
N2 C5 1.334(2) .
N2 C1 1.340(2) .
C1 C2 1.377(2) .
C1 H1 0.99(2) .
C2 C3 1.396(2) .
C2 H2 0.969(19) .
C3 C4 1.388(2) .
C3 C3 1.486(3) 2_655
C4 C5 1.378(2) .
C4 H4 0.952(19) .
C5 H5 0.96(2) .
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
O1 H11 N2 1.05(3) 1.58(3) 2.6250(18) 176(3)
N1 H12 O2 0.89(2) 1.92(2) 2.6661(19) 141.0(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139147798
