#------------------------------------------------------------------------------
#$Date: 2022-08-29 11:05:46 +0200 (Mon 29 de Aug de 2022) $
#$Revision: 277433 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/57/8105706.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_8105706
loop_
_publ_author_name
'Angevine, Devin J.'
'Benedict, Jason B.'
_publ_section_title
;
 The co-crystal structure of 4-hydroxy-3-methoxybenzoic acid --
 4,4′-bipyridine, C8H8O4·C10H8N2
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              397
_journal_page_last               398
_journal_paper_doi               10.1515/ncrs-2022-0088
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C8 H8 O4, C10 H8 N2'
_chemical_formula_sum            'C18 H16 N2 O4'
_chemical_formula_weight         324.33
_chemical_name_systematic
'4-Hydroxy-3-Methoxybenzoic Acid 4,4'-Bipyridine'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 116.124(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.427(4)
_cell_length_b                   10.069(3)
_cell_length_c                   12.751(4)
_cell_measurement_reflns_used    5225
_cell_measurement_temperature    90.0
_cell_measurement_theta_max      28.82
_cell_measurement_theta_min      2.64
_cell_volume                     1547.8(8)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      90.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24407
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.985
_diffrn_reflns_theta_min         1.689
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1360 before and 0.0650 after correction.
The Ratio of minimum to maximum transmission is 0.8210.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_preparation       'slow evaporation from methanol'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0564P)²+0.4299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1152
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3215
_reflns_number_total             4098
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0088_suppl.cif
_cod_data_source_block           p-vanillic_acid+4,4-bipy
_cod_database_code               8105706
_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_max   0.998
_shelx_estimated_absorpt_t_min   0.966
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C7(H7), C15(H15), C16(H16), C12(H12), C13(H13), C9(H9),
 C18(H18), C10(H10), C17(H17)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.09607(10) 0.45834(13) 0.80850(11) 0.0167(3) Uani 1 1 d . . . . .
C2 C 0.99142(10) 0.46545(12) 0.82183(11) 0.0154(2) Uani 1 1 d . . . . .
C3 C 0.97455(10) 0.37150(12) 0.89381(11) 0.0159(2) Uani 1 1 d . . . . .
H3 H 1.029132 0.305530 0.932321 0.019 Uiso 1 1 calc R U . . .
C4 C 0.87823(10) 0.37483(12) 0.90882(11) 0.0153(2) Uani 1 1 d . . . . .
C5 C 0.92922(11) 0.18543(13) 1.03420(12) 0.0205(3) Uani 1 1 d . . . . .
H5A H 0.946260 0.136130 0.977827 0.031 Uiso 1 1 calc R U . . .
H5B H 0.897505 0.124807 1.071614 0.031 Uiso 1 1 calc R U . . .
H5C H 0.997416 0.224875 1.093751 0.031 Uiso 1 1 calc R U . . .
C6 C 0.79791(10) 0.47377(12) 0.85243(11) 0.0158(2) Uani 1 1 d . . . . .
C7 C 0.81397(11) 0.56382(12) 0.77869(11) 0.0176(3) Uani 1 1 d . . . . .
H7 H 0.758598 0.628350 0.738390 0.021 Uiso 1 1 calc R U . . .
C8 C 0.91054(11) 0.56047(12) 0.76321(11) 0.0169(3) Uani 1 1 d . . . . .
H8 H 0.921056 0.622671 0.712961 0.020 Uiso 1 1 calc R U . . .
C9 C 0.66153(11) 0.25859(13) 0.57113(12) 0.0201(3) Uani 1 1 d . . . . .
H9 H 0.738985 0.275912 0.608242 0.024 Uiso 1 1 calc R U . . .
C10 C 0.59381(10) 0.32881(13) 0.60809(11) 0.0182(3) Uani 1 1 d . . . . .
H10 H 0.624593 0.393448 0.668170 0.022 Uiso 1 1 calc R U . . .
C11 C 0.47967(10) 0.30336(12) 0.55590(11) 0.0155(2) Uani 1 1 d . . . . .
C12 C 0.43914(11) 0.20780(13) 0.46776(12) 0.0193(3) Uani 1 1 d . . . . .
H12 H 0.362390 0.186513 0.430581 0.023 Uiso 1 1 calc R U . . .
C13 C 0.51320(11) 0.14449(13) 0.43552(12) 0.0208(3) Uani 1 1 d . . . . .
H13 H 0.484632 0.080936 0.374279 0.025 Uiso 1 1 calc R U . . .
C14 C 0.40541(10) 0.37396(12) 0.59617(11) 0.0157(2) Uani 1 1 d . . . . .
C15 C 0.42670(11) 0.50417(13) 0.63812(11) 0.0180(3) Uani 1 1 d . . . . .
H15 H 0.488739 0.551079 0.639722 0.022 Uiso 1 1 calc R U . . .
C16 C 0.35639(11) 0.56438(13) 0.67743(12) 0.0193(3) Uani 1 1 d . . . . .
H16 H 0.371066 0.653584 0.704153 0.023 Uiso 1 1 calc R U . . .
C17 C 0.24845(11) 0.37797(14) 0.63836(13) 0.0224(3) Uani 1 1 d . . . . .
H17 H 0.186313 0.333192 0.638701 0.027 Uiso 1 1 calc R U . . .
C18 C 0.31262(11) 0.31054(13) 0.59541(13) 0.0213(3) Uani 1 1 d . . . . .
H18 H 0.293845 0.222744 0.565984 0.026 Uiso 1 1 calc R U . . .
N1 N 0.62331(9) 0.16781(11) 0.48594(10) 0.0201(2) Uani 1 1 d . . . . .
N2 N 0.26870(9) 0.50268(11) 0.67950(10) 0.0198(2) Uani 1 1 d . . . . .
O1 O 1.10629(8) 0.55635(9) 0.74365(9) 0.0222(2) Uani 1 1 d . . . . .
H1 H 1.172(2) 0.541(2) 0.730(2) 0.061(7) Uiso 1 1 d . . . . .
O2 O 1.16489(8) 0.37046(10) 0.85106(9) 0.0224(2) Uani 1 1 d . . . . .
O3 O 0.85112(7) 0.28829(9) 0.97499(8) 0.0195(2) Uani 1 1 d . . . . .
O4 O 0.70308(7) 0.48247(9) 0.86544(8) 0.0189(2) Uani 1 1 d . . . . .
H4 H 0.6996(18) 0.421(2) 0.917(2) 0.053(6) 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_1
_geom_angle_site_symmetry_3
C6 O4 H4 112.9(14) . .
C1 O1 H1 109.7(13) . .
C4 O3 C5 117.01(10) . .
C17 N2 C16 117.01(11) . .
C9 N1 C13 117.04(11) . .
O4 C6 C4 122.08(11) . .
O4 C6 C7 118.29(11) . .
C7 C6 C4 119.62(11) . .
C3 C2 C1 118.29(11) . .
C8 C2 C3 120.11(11) . .
C8 C2 C1 121.58(11) . .
C15 C14 C11 121.69(11) . .
C18 C14 C11 120.70(12) . .
C18 C14 C15 117.60(12) . .
C2 C3 H3 119.9 . .
C4 C3 C2 120.12(11) . .
C4 C3 H3 119.9 . .
C12 C11 C14 121.64(11) . .
C12 C11 C10 117.79(11) . .
C10 C11 C14 120.55(12) . .
O3 C4 C6 114.37(11) . .
O3 C4 C3 125.87(11) . .
C3 C4 C6 119.76(11) . .
C2 C8 H8 120.2 . .
C2 C8 C7 119.63(12) . .
C7 C8 H8 120.2 . .
C6 C7 C8 120.70(12) . .
C6 C7 H7 119.6 . .
C8 C7 H7 119.6 . .
C14 C15 H15 120.3 . .
C16 C15 C14 119.42(12) . .
C16 C15 H15 120.3 . .
O1 C1 C2 113.28(11) . .
O2 C1 O1 123.23(12) . .
O2 C1 C2 123.48(12) . .
N2 C16 C15 123.17(12) . .
N2 C16 H16 118.4 . .
C15 C16 H16 118.4 . .
C11 C12 H12 120.7 . .
C13 C12 C11 118.65(12) . .
C13 C12 H12 120.7 . .
N1 C13 C12 123.87(13) . .
N1 C13 H13 118.1 . .
C12 C13 H13 118.1 . .
N1 C9 H9 118.3 . .
N1 C9 C10 123.34(12) . .
C10 C9 H9 118.3 . .
C14 C18 H18 120.6 . .
C17 C18 C14 118.79(13) . .
C17 C18 H18 120.6 . .
O3 C5 H5A 109.5 . .
O3 C5 H5B 109.5 . .
O3 C5 H5C 109.5 . .
H5A C5 H5B 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C11 C10 H10 120.4 . .
C9 C10 C11 119.29(12) . .
C9 C10 H10 120.4 . .
N2 C17 C18 123.98(12) . .
N2 C17 H17 118.0 . .
C18 C17 H17 118.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O4 C6 1.3575(15) .
O4 H4 0.92(2) .
O1 C1 1.3329(16) .
O1 H1 0.99(2) .
O3 C4 1.3690(15) .
O3 C5 1.4301(16) .
O2 C1 1.2205(16) .
N2 C16 1.3418(17) .
N2 C17 1.3418(18) .
N1 C13 1.3480(18) .
N1 C9 1.3372(18) .
C6 C4 1.4105(18) .
C6 C7 1.3896(18) .
C2 C3 1.4042(17) .
C2 C8 1.3922(18) .
C2 C1 1.4896(17) .
C14 C11 1.4879(17) .
C14 C15 1.3972(18) .
C14 C18 1.3963(18) .
C3 H3 0.9500 .
C3 C4 1.3886(18) .
C11 C12 1.3952(18) .
C11 C10 1.3997(18) .
C8 H8 0.9500 .
C8 C7 1.3954(18) .
C7 H7 0.9500 .
C15 H15 0.9500 .
C15 C16 1.3880(18) .
C16 H16 0.9500 .
C12 H12 0.9500 .
C12 C13 1.3871(18) .
C13 H13 0.9500 .
C9 H9 0.9500 .
C9 C10 1.3879(18) .
C18 H18 0.9500 .
C18 C17 1.3853(19) .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C10 H10 0.9500 .
C17 H17 0.9500 .
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
_geom_hbond_publ_flag
C12 H12 O2 0.95 2.45 3.4015(19) 175.2 4_465 yes
C18 H18 O4 0.95 2.57 3.3613(19) 141.3 2_646 yes
C10 H10 O4 0.95 2.43 3.3279(18) 157.5 . yes
O4 H4 N1 0.92(2) 1.85(2) 2.6920(15) 152(2) 4_566 yes
O1 H1 N2 0.99(2) 1.73(2) 2.6995(15) 169(2) 1_655 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O4 C6 C4 O3 1.18(17) . . . .
O4 C6 C4 C3 -179.11(11) . . . .
O4 C6 C7 C8 179.20(11) . . . .
N1 C9 C10 C11 1.0(2) . . . .
C2 C3 C4 O3 179.04(11) . . . .
C2 C3 C4 C6 -0.64(18) . . . .
C2 C8 C7 C6 0.33(19) . . . .
C14 C11 C12 C13 -179.14(12) . . . .
C14 C11 C10 C9 178.08(12) . . . .
C14 C15 C16 N2 1.3(2) . . . .
C14 C18 C17 N2 1.1(2) . . . .
C3 C2 C8 C7 1.58(19) . . . .
C3 C2 C1 O1 -176.50(11) . . . .
C3 C2 C1 O2 4.61(19) . . . .
C11 C14 C15 C16 -178.36(12) . . . .
C11 C14 C18 C17 177.24(12) . . . .
C11 C12 C13 N1 1.3(2) . . . .
C4 C6 C7 C8 -2.37(19) . . . .
C8 C2 C3 C4 -1.41(18) . . . .
C8 C2 C1 O1 4.78(17) . . . .
C8 C2 C1 O2 -174.11(12) . . . .
C7 C6 C4 O3 -177.19(11) . . . .
C7 C6 C4 C3 2.52(18) . . . .
C15 C14 C11 C12 -149.09(13) . . . .
C15 C14 C11 C10 32.61(18) . . . .
C15 C14 C18 C17 -1.5(2) . . . .
C1 C2 C3 C4 179.85(11) . . . .
C1 C2 C8 C7 -179.72(11) . . . .
C16 N2 C17 C18 0.5(2) . . . .
C12 C11 C10 C9 -0.29(19) . . . .
C13 N1 C9 C10 -0.5(2) . . . .
C9 N1 C13 C12 -0.7(2) . . . .
C18 C14 C11 C12 32.24(19) . . . .
C18 C14 C11 C10 -146.06(13) . . . .
C18 C14 C15 C16 0.35(19) . . . .
C5 O3 C4 C6 179.87(11) . . . .
C5 O3 C4 C3 0.17(18) . . . .
C10 C11 C12 C13 -0.79(19) . . . .
C17 N2 C16 C15 -1.7(2) . . . .
