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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/4/51/24/4512412.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_4512412
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(C14 H12 Cl N O2), C10 H8 N2'
_chemical_formula_sum            'C38 H32 Cl2 N4 O4'
_chemical_formula_weight         679.58
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.911(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.7315(12)
_cell_length_b                   45.263(12)
_cell_length_c                   7.929(2)
_cell_measurement_reflns_used    6181
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      28.261
_cell_measurement_theta_min      2.700
_cell_volume                     1624.7(7)
_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      183(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       57
_diffrn_reflns_limit_k_min       -57
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13525
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.80
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.9755
_exptl_absorpt_correction_T_min  0.9404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3508
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0493
_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)+(0.0268P)²+1.1587P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1086
_reflns_number_gt                3094
_reflns_number_total             3508
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg5012633_si_006.cif
_cod_data_source_block           TFA-BP
_cod_depositor_comments
'Adding full bibliography for 4512412--4512416.cif.'
_cod_original_cell_volume        1624.6(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4512412
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
Cl1 Cl 0.36688(14) 0.246345(12) 0.34010(8) 0.05084(18) Uani 1 1 d
N1 N 0.5399(4) 0.35922(4) 0.3821(2) 0.0383(4) Uani 1 1 d
O1 O 0.8596(4) 0.40535(3) 0.33754(19) 0.0464(4) Uani 1 1 d
O2 O 0.9899(4) 0.43882(4) 0.5515(2) 0.0539(4) Uani 1 1 d
C11 C 0.7239(4) 0.39734(4) 0.6009(2) 0.0349(4) Uani 1 1 d
C12 C 0.5590(4) 0.37132(4) 0.5430(2) 0.0336(4) Uani 1 1 d
C13 C 0.4146(5) 0.35812(5) 0.6559(3) 0.0419(5) Uani 1 1 d
C14 C 0.4421(6) 0.36947(6) 0.8202(3) 0.0492(6) Uani 1 1 d
C15 C 0.6144(6) 0.39406(6) 0.8811(3) 0.0531(7) Uani 1 1 d
C16 C 0.7503(6) 0.40778(5) 0.7717(3) 0.0456(5) Uani 1 1 d
C17 C 0.8632(5) 0.41351(4) 0.4848(3) 0.0390(5) Uani 1 1 d
C21 C 0.3645(4) 0.33438(4) 0.3071(2) 0.0325(4) Uani 1 1 d
C22 C 0.1099(5) 0.33923(5) 0.1687(3) 0.0400(5) Uani 1 1 d
C23 C -0.0580(5) 0.31587(5) 0.0838(3) 0.0444(5) Uani 1 1 d
C24 C 0.0235(5) 0.28736(5) 0.1382(3) 0.0408(5) Uani 1 1 d
C25 C 0.2749(4) 0.28282(4) 0.2769(3) 0.0344(4) Uani 1 1 d
C26 C 0.4537(4) 0.30566(4) 0.3657(2) 0.0316(4) Uani 1 1 d
C27 C 0.7274(5) 0.29979(6) 0.5146(3) 0.0425(5) Uani 1 1 d
N2 N 0.1863(4) 0.46725(4) 0.3107(3) 0.0513(5) Uani 1 1 d
C1 C 0.2439(6) 0.49614(5) 0.3124(4) 0.0569(6) Uani 1 1 d
C2 C 0.3669(6) 0.50948(5) 0.1954(4) 0.0534(6) Uani 1 1 d
C3 C 0.4337(4) 0.49325(4) 0.0650(3) 0.0429(5) Uani 1 1 d
C4 C 0.3693(6) 0.46331(5) 0.0619(4) 0.0613(7) Uani 1 1 d
C5 C 0.2501(6) 0.45141(5) 0.1843(4) 0.0588(7) Uani 1 1 d
H11 H 0.617(5) 0.3693(5) 0.320(3) 0.044(6) Uiso 1 1 d
H21 H 1.050(6) 0.4477(6) 0.475(4) 0.067(9) Uiso 1 1 d
H1 H 0.186(7) 0.5074(7) 0.401(4) 0.080(9) Uiso 1 1 d
H2 H 0.404(6) 0.5299(6) 0.205(3) 0.060(7) Uiso 1 1 d
H4 H 0.407(7) 0.4517(7) -0.020(4) 0.080(10) Uiso 1 1 d
H5 H 0.219(6) 0.4304(6) 0.187(4) 0.075(9) Uiso 1 1 d
H13 H 0.293(6) 0.3414(6) 0.612(3) 0.054(7) Uiso 1 1 d
H14 H 0.345(5) 0.3612(5) 0.894(3) 0.052(7) Uiso 1 1 d
H15 H 0.639(6) 0.4019(6) 0.994(4) 0.065(8) Uiso 1 1 d
H16 H 0.875(5) 0.4244(5) 0.814(3) 0.045(6) Uiso 1 1 d
H22 H 0.060(5) 0.3595(5) 0.130(3) 0.048(6) Uiso 1 1 d
H23 H -0.236(5) 0.3196(5) -0.010(3) 0.046(6) Uiso 1 1 d
H24 H -0.085(5) 0.2714(5) 0.085(3) 0.044(6) Uiso 1 1 d
H27A H 0.673(7) 0.2907(7) 0.611(4) 0.085(10) Uiso 1 1 d
H27B H 0.856(6) 0.2859(6) 0.480(4) 0.070(8) Uiso 1 1 d
H27C H 0.832(6) 0.3167(6) 0.554(4) 0.070(9) 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'
Cl Cl 0.1484 0.1585 '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 125.41(17) .
C12 N1 H11 114.4(16) .
C21 N1 H11 119.4(16) .
C17 O2 H21 109(2) .
C16 C11 C12 118.6(2) .
C16 C11 C17 120.3(2) .
C12 C11 C17 121.11(17) .
N1 C12 C13 120.73(19) .
N1 C12 C11 121.11(18) .
C13 C12 C11 118.16(18) .
C14 C13 C12 121.1(2) .
C14 C13 H13 121.7(15) .
C12 C13 H13 117.2(15) .
C13 C14 C15 121.1(2) .
C13 C14 H14 121.7(16) .
C15 C14 H14 117.2(15) .
C16 C15 C14 118.9(2) .
C16 C15 H15 118.9(17) .
C14 C15 H15 122.3(17) .
C15 C16 C11 122.1(2) .
C15 C16 H16 119.6(14) .
C11 C16 H16 118.3(14) .
O1 C17 O2 121.4(2) .
O1 C17 C11 124.27(18) .
O2 C17 C11 114.31(19) .
C22 C21 C26 121.02(18) .
C22 C21 N1 118.13(18) .
C26 C21 N1 120.79(18) .
C23 C22 C21 120.6(2) .
C23 C22 H22 121.3(14) .
C21 C22 H22 118.1(14) .
C22 C23 C24 119.8(2) .
C22 C23 H23 119.7(14) .
C24 C23 H23 120.5(14) .
C23 C24 C25 119.1(2) .
C23 C24 H24 121.7(14) .
C25 C24 H24 119.2(14) .
C24 C25 C26 123.29(19) .
C24 C25 Cl1 117.09(16) .
C26 C25 Cl1 119.62(15) .
C25 C26 C21 116.17(17) .
C25 C26 C27 121.70(19) .
C21 C26 C27 122.13(18) .
C26 C27 H27A 109.2(19) .
C26 C27 H27B 111.4(17) .
H27A C27 H27B 106(2) .
C26 C27 H27C 112.2(18) .
H27A C27 H27C 109(2) .
H27B C27 H27C 109(2) .
C1 N2 C5 116.3(2) .
N2 C1 C2 123.4(2) .
N2 C1 H1 114.9(18) .
C2 C1 H1 121.6(18) .
C1 C2 C3 120.5(2) .
C1 C2 H2 119.0(16) .
C3 C2 H2 120.5(16) .
C2 C3 C4 115.9(2) .
C2 C3 C3 122.5(2) 3_665
C4 C3 C3 121.6(3) 3_665
C5 C4 C3 120.4(3) .
C5 C4 H4 120(2) .
C3 C4 H4 120(2) .
N2 C5 C4 123.4(2) .
N2 C5 H5 116.6(17) .
C4 C5 H5 119.8(17) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C25 1.743(2) .
N1 C12 1.367(2) .
N1 C21 1.421(2) .
N1 H11 0.83(2) .
O1 C17 1.220(2) .
O2 C17 1.329(2) .
O2 H21 0.84(3) .
C11 C16 1.405(3) .
C11 C12 1.414(3) .
C11 C17 1.473(3) .
C12 C13 1.407(3) .
C13 C14 1.371(3) .
C13 H13 0.95(3) .
C14 C15 1.381(4) .
C14 H14 0.92(3) .
C15 C16 1.369(4) .
C15 H15 0.94(3) .
C16 H16 0.95(2) .
C21 C22 1.391(3) .
C21 C26 1.403(3) .
C22 C23 1.375(3) .
C22 H22 0.97(2) .
C23 C24 1.380(3) .
C23 H23 0.96(2) .
C24 C25 1.380(3) .
C24 H24 0.91(2) .
C25 C26 1.391(3) .
C26 C27 1.500(3) .
C27 H27A 0.97(3) .
C27 H27B 0.97(3) .
C27 H27C 0.92(3) .
N2 C1 1.335(3) .
N2 C5 1.336(3) .
C1 C2 1.370(4) .
C1 H1 0.97(3) .
C2 C3 1.378(3) .
C2 H2 0.94(3) .
C3 C4 1.388(3) .
C3 C3 1.485(5) 3_665
C4 C5 1.367(4) .
C4 H4 0.89(3) .
C5 H5 0.96(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
N1 H11 O1 0.83(2) 1.98(2) 2.662(2) 139(2) .
O2 H21 N2 0.84(3) 1.84(3) 2.683(3) 179(3) 1_655
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_4
C21 N1 C12 C13 4.5(3) . .
C21 N1 C12 C11 -175.54(19) . .
C16 C11 C12 N1 -176.25(19) . .
C17 C11 C12 N1 4.5(3) . .
C16 C11 C12 C13 3.7(3) . .
C17 C11 C12 C13 -175.61(18) . .
N1 C12 C13 C14 177.4(2) . .
C11 C12 C13 C14 -2.5(3) . .
C12 C13 C14 C15 -0.6(3) . .
C13 C14 C15 C16 2.4(4) . .
C14 C15 C16 C11 -1.1(3) . .
C12 C11 C16 C15 -2.0(3) . .
C17 C11 C16 C15 177.3(2) . .
C16 C11 C17 O1 177.2(2) . .
C12 C11 C17 O1 -3.5(3) . .
C16 C11 C17 O2 -4.6(3) . .
C12 C11 C17 O2 174.67(18) . .
C12 N1 C21 C22 106.7(2) . .
C12 N1 C21 C26 -76.3(3) . .
C26 C21 C22 C23 -1.2(3) . .
N1 C21 C22 C23 175.82(19) . .
C21 C22 C23 C24 1.2(3) . .
C22 C23 C24 C25 -0.5(3) . .
C23 C24 C25 C26 -0.2(3) . .
C23 C24 C25 Cl1 179.94(17) . .
C24 C25 C26 C21 0.2(3) . .
Cl1 C25 C26 C21 -179.90(14) . .
C24 C25 C26 C27 -179.3(2) . .
Cl1 C25 C26 C27 0.6(3) . .
C22 C21 C26 C25 0.4(3) . .
N1 C21 C26 C25 -176.47(17) . .
C22 C21 C26 C27 179.96(19) . .
N1 C21 C26 C27 3.0(3) . .
C5 N2 C1 C2 -1.2(4) . .
N2 C1 C2 C3 1.2(4) . .
C1 C2 C3 C4 -0.1(4) . .
C1 C2 C3 C3 179.8(3) . 3_665
C2 C3 C4 C5 -0.7(4) . .
C3 C3 C4 C5 179.3(3) 3_665 .
C1 N2 C5 C4 0.3(4) . .
C3 C4 C5 N2 0.6(5) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139044819
