A 2:1 co-crystal of 2-methylbenzoic acid and <i>N</i>,<i>N</i>'-bis(pyridin-4-ylmethyl)ethanediamide: crystal structure and Hirshfeld surface analysis
Syed, Sabrina; Jotani, Mukesh M.; Halim, Siti Nadiah Abdul; Tiekink, Edward R. T.; Acta Crystallographica Section E 72 (2016) 391–398; doi:10.1107/S2056989016002735

data_2241576
_publ_section_title
;
 A 2:1 co-crystal of 2-methylbenzoic acid and
 <i>N</i>,<i>N</i>'-bis(pyridin-4-ylmethyl)ethanediamide: crystal
 structure and Hirshfeld surface analysis
;
_journal_coeditor_code           HB7566
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              391
_journal_page_last               398
_journal_paper_doi               10.1107/S2056989016002735
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C14 H14 N4 O2, 2C8 H8 O2'
_chemical_formula_moiety         'C14 H14 N4 O2, 2(C8 H8 O2)'
_chemical_formula_sum            'C30 H30 N4 O6'
_chemical_formula_weight         542.58
_chemical_name_systematic
;
2-Methylbenzoic acid--\
<i>N</i>,<i>N</i>'-bis(pyridin-4-ylmethyl)ethanediamide (2/1)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                82.971(5)
_cell_angle_beta                 81.638(6)
_cell_angle_gamma                85.686(5)
_cell_formula_units_Z            1
_cell_length_a                   6.8948(5)
_cell_length_b                   9.7219(5)
_cell_length_c                   9.9621(7)
_cell_measurement_reflns_used    3840
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.97
_cell_measurement_theta_min      3.53
_cell_volume                     654.58(8)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2014)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg,
2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Agilent Technologies SuperNova Dual diffractometer with an Atlas detector'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15067
_diffrn_reflns_theta_full        27.496
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.991
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       prism
_exptl_crystal_F_000             286
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.231
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2993
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0577
_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
'w=1/[\s^2^(Fo^2^)+(0.0434P)^2^+0.2225P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1060
_reflns_number_gt                2358
_reflns_number_total             2993
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7566sup1.cif
_cod_data_source_block           I
_cod_database_code               2241576
_cod_database_fobs_code          2241576
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.990
_shelx_hkl_checksum              52641
_shelx_res_checksum              69217