Crystal structure, Hirshfeld surface analysis and computational study of the 1:2 co-crystal formed between <i>N</i>,<i>N</i>'-bis(pyridin-4-ylmethyl)ethanediamide and 4-chlorobenzoic acid
Tan, Sang Loon; Tiekink, Edward R. T.; Acta Crystallographica Section E 76 (2020) 245–253; doi:10.1107/S2056989020000572

data_2243262
_publ_section_title
;
 Crystal structure, Hirshfeld surface analysis and computational study of
 the 1:2 co-crystal formed between
 <i>N</i>,<i>N</i>'-bis(pyridin-4-ylmethyl)ethanediamide and
 4-chlorobenzoic acid
;
_journal_coeditor_code           HB7889
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              245
_journal_page_last               253
_journal_paper_doi               10.1107/S2056989020000572
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C14 H14 N4 O2, 2C7 H5 Cl O2'
_chemical_formula_moiety         'C14 H14 N4 O2, 2(C7 H5 Cl O2)'
_chemical_formula_sum            'C28 H24 Cl2 N4 O6'
_chemical_formula_weight         583.41
_chemical_name_systematic
'<i>N</i>,<i>N</i>'-Bis(pyridin-4-ylmethyl)ethanediamide--4-chlorobenzoic acid (1/2)'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                78.871(2)
_cell_angle_beta                 78.816(2)
_cell_angle_gamma                81.992(2)
_cell_formula_units_Z            2
_cell_length_a                   9.9401(2)
_cell_length_b                   11.2002(2)
_cell_length_c                   12.3308(3)
_cell_measurement_reflns_used    14644
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.1260
_cell_measurement_theta_min      3.6990
_cell_volume                     1313.98(5)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg,
2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.2558
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            33133
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.466
_diffrn_reflns_theta_min         3.709
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.668
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.847
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2018)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       plate
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.127
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.333
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         5486
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0315
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0502P)^2^+0.3813P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0904
_reflns_number_gt                4814
_reflns_number_total             5486
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7889sup1.cif
_cod_data_source_block           I
_cod_database_code               2243262
_cod_database_fobs_code          2243262
_shelx_estimated_absorpt_t_min   0.728
_shelx_estimated_absorpt_t_max   0.936
_shelx_hkl_checksum              15199
_shelx_res_checksum              64957