The co-crystal structure of 4-hydroxy-3-methoxybenzoic acid – 4,4′-bipyridine, C8H8O4·C10H8N2
Angevine, Devin J.; Benedict, Jason B.; Zeitschrift für Kristallographie - New Crystal Structures 237 (2022) 397–398; doi:10.1515/ncrs-2022-0088

data_8105706
_publ_section_title
;
 The co-crystal structure of 4-hydroxy-3-methoxybenzoic acid --
 4,4&#x2032;-bipyridine, C8H8O4&#x00B7;C10H8N2
;
_journal_issue                   3
_journal_name_full
'Zeitschrift f\"ur 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       '\f and \w 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 \l/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/[\s^2^(Fo^2^)+(0.0564P)^2^+0.4299P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_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)
;
_shelx_res_checksum              6568
_shelx_hkl_checksum              13360
_olex2_submission_special_instructions 'No special instructions were received'