#------------------------------------------------------------------------------
#$Date: 2025-08-21 04:34:05 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301843 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/24/4512414.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_4512414
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(C15 H15 N O2), C10 H8 N2'
_chemical_formula_sum            'C40 H38 N4 O4'
_chemical_formula_weight         638.74
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.276(1)
_cell_angle_beta                 99.368(1)
_cell_angle_gamma                98.738(1)
_cell_formula_units_Z            1
_cell_length_a                   7.3302(4)
_cell_length_b                   8.6992(5)
_cell_length_c                   13.6719(8)
_cell_measurement_reflns_used    4522
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      30.500
_cell_measurement_theta_min      2.494
_cell_volume                     807.55(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      183(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  0.0151
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8341
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.49
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9649
_exptl_absorpt_correction_T_min  0.9600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             338
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3878
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0406
_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)+(0.0591P)²+0.1805P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1137
_reflns_number_gt                3311
_reflns_number_total             3878
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg5012633_si_003.cif
_cod_data_source_block           MFA-BP
_cod_depositor_comments
'Adding full bibliography for 4512412--4512416.cif.'
_cod_database_code               4512414
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.25476(15) 0.53453(12) 0.37384(8) 0.0310(2) Uani 1 1 d
O1 O 0.22868(14) 0.24706(10) 0.23216(7) 0.0405(2) Uani 1 1 d
O2 O 0.34588(14) 0.23935(12) 0.09133(7) 0.0395(2) Uani 1 1 d
C11 C 0.37343(15) 0.49866(14) 0.21431(8) 0.0273(2) Uani 1 1 d
C12 C 0.34111(14) 0.59976(13) 0.30874(8) 0.0262(2) Uani 1 1 d
C13 C 0.40229(16) 0.77045(15) 0.33405(10) 0.0319(2) Uani 1 1 d
C14 C 0.49118(18) 0.83742(17) 0.26970(11) 0.0390(3) Uani 1 1 d
C15 C 0.52487(18) 0.73870(18) 0.17790(11) 0.0400(3) Uani 1 1 d
C16 C 0.46583(16) 0.57139(17) 0.15121(10) 0.0338(3) Uani 1 1 d
C17 C 0.30907(15) 0.31941(14) 0.18144(8) 0.0288(2) Uani 1 1 d
C21 C 0.20594(15) 0.62812(12) 0.46609(8) 0.0262(2) Uani 1 1 d
C22 C 0.31561(16) 0.64065(14) 0.56206(9) 0.0302(2) Uani 1 1 d
C23 C 0.26795(17) 0.72400(15) 0.65324(9) 0.0323(3) Uani 1 1 d
C24 C 0.11130(16) 0.79526(13) 0.64837(9) 0.0290(2) Uani 1 1 d
C25 C -0.00028(15) 0.78376(13) 0.55309(9) 0.0261(2) Uani 1 1 d
C26 C 0.04712(15) 0.69944(13) 0.45997(8) 0.0260(2) Uani 1 1 d
C27 C -0.17322(18) 0.85812(17) 0.55011(11) 0.0359(3) Uani 1 1 d
C28 C -0.07247(19) 0.68528(17) 0.35639(10) 0.0362(3) Uani 1 1 d
N2 N 0.19372(16) 0.91949(13) 0.04075(8) 0.0368(2) Uani 1 1 d
C1 C 0.2135(2) 0.80081(18) -0.04081(10) 0.0423(3) Uani 1 1 d
C2 C 0.1403(2) 0.63710(17) -0.05968(10) 0.0406(3) Uani 1 1 d
C3 C 0.03913(16) 0.58767(15) 0.00777(8) 0.0303(2) Uani 1 1 d
C4 C 0.0159(2) 0.71183(17) 0.09147(10) 0.0406(3) Uani 1 1 d
C5 C 0.0948(2) 0.87215(17) 0.10482(11) 0.0430(3) Uani 1 1 d
H11 H 0.216(2) 0.428(2) 0.3516(13) 0.047(4) Uiso 1 1 d
H21 H 0.289(3) 0.124(3) 0.0731(17) 0.081(7) Uiso 1 1 d
H13 H 0.381(2) 0.840(2) 0.3977(13) 0.043(4) Uiso 1 1 d
H14 H 0.533(2) 0.957(2) 0.2912(13) 0.049(4) Uiso 1 1 d
H15 H 0.587(2) 0.7862(19) 0.1334(13) 0.045(4) Uiso 1 1 d
H16 H 0.485(2) 0.4986(19) 0.0869(12) 0.040(4) Uiso 1 1 d
H22 H 0.425(2) 0.5891(19) 0.5630(12) 0.041(4) Uiso 1 1 d
H23 H 0.344(2) 0.7324(18) 0.7205(13) 0.041(4) Uiso 1 1 d
H24 H 0.075(2) 0.8526(18) 0.7134(12) 0.037(4) Uiso 1 1 d
H27A H -0.168(2) 0.937(2) 0.5111(13) 0.050(4) Uiso 1 1 d
H27B H -0.293(3) 0.771(2) 0.5152(14) 0.058(5) Uiso 1 1 d
H27C H -0.185(2) 0.915(2) 0.6219(14) 0.055(5) Uiso 1 1 d
H28A H -0.212(3) 0.645(2) 0.3514(14) 0.063(5) Uiso 1 1 d
H28B H -0.042(3) 0.606(2) 0.2998(15) 0.058(5) Uiso 1 1 d
H28C H -0.059(3) 0.789(3) 0.3426(15) 0.069(6) Uiso 1 1 d
H1 H 0.289(2) 0.838(2) -0.0876(14) 0.054(5) Uiso 1 1 d
H2 H 0.161(3) 0.561(2) -0.1186(15) 0.063(5) Uiso 1 1 d
H4 H -0.051(3) 0.692(2) 0.1443(14) 0.057(5) Uiso 1 1 d
H5 H 0.086(2) 0.962(2) 0.1627(14) 0.051(4) 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'
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 124.73(9) .
C12 N1 H11 115.3(11) .
C21 N1 H11 119.5(11) .
C17 O2 H21 109.2(13) .
C16 C11 C12 119.32(11) .
C16 C11 C17 119.78(10) .
C12 C11 C17 120.90(10) .
N1 C12 C13 120.62(10) .
N1 C12 C11 121.52(10) .
C13 C12 C11 117.87(10) .
C14 C13 C12 121.14(12) .
C14 C13 H13 120.3(9) .
C12 C13 H13 118.6(9) .
C13 C14 C15 121.10(12) .
C13 C14 H14 118.1(10) .
C15 C14 H14 120.8(10) .
C16 C15 C14 118.88(11) .
C16 C15 H15 120.4(10) .
C14 C15 H15 120.7(10) .
C15 C16 C11 121.69(12) .
C15 C16 H16 121.1(9) .
C11 C16 H16 117.2(9) .
O1 C17 O2 121.34(11) .
O1 C17 C11 123.68(10) .
O2 C17 C11 114.97(10) .
C22 C21 C26 120.93(10) .
C22 C21 N1 118.13(10) .
C26 C21 N1 120.89(10) .
C23 C22 C21 119.89(10) .
C23 C22 H22 121.7(9) .
C21 C22 H22 118.4(9) .
C22 C23 C24 119.80(11) .
C22 C23 H23 120.0(9) .
C24 C23 H23 120.2(9) .
C23 C24 C25 121.12(10) .
C23 C24 H24 119.9(8) .
C25 C24 H24 119.0(8) .
C24 C25 C26 119.50(10) .
C24 C25 C27 119.98(10) .
C26 C25 C27 120.51(10) .
C21 C26 C25 118.75(10) .
C21 C26 C28 121.08(10) .
C25 C26 C28 120.16(10) .
C25 C27 H27A 111.2(10) .
C25 C27 H27B 111.3(10) .
H27A C27 H27B 107.4(14) .
C25 C27 H27C 110.5(10) .
H27A C27 H27C 108.7(14) .
H27B C27 H27C 107.5(14) .
C26 C28 H28A 112.5(11) .
C26 C28 H28B 112.0(11) .
H28A C28 H28B 104.2(15) .
C26 C28 H28C 111.8(12) .
H28A C28 H28C 107.4(16) .
H28B C28 H28C 108.5(16) .
C5 N2 C1 116.28(12) .
N2 C1 C2 123.52(12) .
N2 C1 H1 115.5(10) .
C2 C1 H1 121.0(10) .
C1 C2 C3 120.18(11) .
C1 C2 H2 118.4(12) .
C3 C2 H2 121.4(12) .
C4 C3 C2 116.10(12) .
C4 C3 C3 121.61(14) 2_565
C2 C3 C3 122.29(13) 2_565
C5 C4 C3 119.89(12) .
C5 C4 H4 116.5(11) .
C3 C4 H4 123.6(11) .
N2 C5 C4 124.02(12) .
N2 C5 H5 113.2(10) .
C4 C5 H5 122.7(10) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C12 1.3683(14) .
N1 C21 1.4288(14) .
N1 H11 0.874(17) .
O1 C17 1.2203(14) .
O2 C17 1.3267(13) .
O2 H21 0.97(2) .
C11 C16 1.4033(15) .
C11 C12 1.4223(15) .
C11 C17 1.4733(16) .
C12 C13 1.4088(16) .
C13 C14 1.3772(17) .
C13 H13 0.961(16) .
C14 C15 1.391(2) .
C14 H14 0.980(17) .
C15 C16 1.378(2) .
C15 H15 0.961(16) .
C16 H16 0.975(15) .
C21 C22 1.3891(16) .
C21 C26 1.4014(15) .
C22 C23 1.3835(16) .
C22 H22 0.978(16) .
C23 C24 1.3863(17) .
C23 H23 0.973(16) .
C24 C25 1.3897(16) .
C24 H24 0.989(15) .
C25 C26 1.4062(15) .
C25 C27 1.5081(16) .
C26 C28 1.5015(16) .
C27 H27A 0.978(18) .
C27 H27B 1.011(19) .
C27 H27C 0.992(18) .
C28 H28A 1.01(2) .
C28 H28B 0.961(19) .
C28 H28C 0.97(2) .
N2 C5 1.3343(18) .
N2 C1 1.3353(16) .
C1 C2 1.378(2) .
C1 H1 0.994(18) .
C2 C3 1.3905(18) .
C2 H2 0.940(19) .
C3 C4 1.3899(16) .
C3 C3 1.488(2) 2_565
C4 C5 1.375(2) .
C4 H4 0.973(18) .
C5 H5 0.961(17) .
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 0.874(17) 1.950(17) 2.6573(13) 137.0(15) .
O2 H21 N2 0.97(2) 1.71(2) 2.6818(15) 179(2) 1_545
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139044818
