Covalent-assisted supramolecular synthesis: the effect of hydrogen bonding in cocrystals of 4-<i>tert</i>-butylbenzoic acid with isoniazid and its derivatized forms
Madeley, Lee G.; Levendis, Demetrius C.; Lemmerer, Andreas; Acta Crystallographica Section C 75 (2019) –; doi:10.1107/S205322961900055X

data_2021461
_publ_section_title
;
 Covalent-assisted supramolecular synthesis: the effect of hydrogen
 bonding in cocrystals of 4-<i>tert</i>-butylbenzoic acid with isoniazid
 and its derivatized forms
;
_journal_coeditor_code           FA3397
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S205322961900055X
_journal_volume                  75
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_iupac          'C19 H15 N3 O, C11 H14 O2'
_chemical_formula_moiety         'C19 H15 N3 O, C11 H14 O2'
_chemical_formula_sum            'C30 H29 N3 O3'
_chemical_formula_weight         479.56
_chemical_name_common
;
4-<i>tert</i>-Butylbenzoic
acid--<i>N</i>'-(diphenylmethylene)isonicotinohydrazide
;
_chemical_name_systematic
;
4-<i>tert</i>-Butylbenzoic
acid--<i>N</i>'-(diphenylmethylene)pyridine-4-carbohydrazide (1/1)
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 93.5050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.69670(10)
_cell_length_b                   10.1984(2)
_cell_length_c                   15.9931(3)
_cell_measurement_reflns_used    6555
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.37
_cell_volume                     1253.01(4)
_computing_cell_refinement
;
SAINT-Plus (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT-Plus and XPREP (Bruker, 2016)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012),
Mercury (Macrae <i>et al.</i>,  2008) and
DIAMOND (Brandenburg, 2006)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12710
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.37
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.9
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause <i>et al.</i>,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.456
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.178
_refine_ls_abs_structure_details
;
The low value of Friedif(stat), 4.9, indicates that the absolute structure
cannot be reliably determined on the basis of the diffraction data."
Flack, H. D. & Bernardinelli, G. (2008). Acta Cryst. A64, 484-493.
Flack, H. D. & Shmueli, U. (2007). Acta Cryst. A63, 257-265. (Equation
8).
;
_refine_ls_abs_structure_Flack   0.5(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5486
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.038
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0496P)^2^+0.1553P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0914
_reflns_number_gt                5107
_reflns_number_total             5486
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            fa3397sup1.cif
_cod_data_source_block           IV
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2021461
_cod_database_fobs_code          2021461
_shelx_hkl_checksum              6962
_shelx_res_checksum              56092