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-yl)methyl]ethanediamide and 3-chlorobenzoic acid
Tan, Sang Loon; Tiekink, Edward R. T.; Acta Crystallographica Section E 76 (2020) 870–876; doi:10.1107/S2056989020006568

data_2243397
_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-yl)methyl]ethanediamide and
 3-chlorobenzoic acid
;
_journal_coeditor_code           WM5558
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              870
_journal_page_last               876
_journal_paper_doi               10.1107/S2056989020006568
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C7 H5 Cl O2, C7 H7 N2 O'
_chemical_formula_moiety         'C7 H5 Cl O2, C7 H7 N2 O'
_chemical_formula_sum            'C14 H12 Cl N2 O3'
_chemical_formula_weight         291.71
_chemical_name_systematic
;
<i>N</i>,<i>N</i>'-Bis[(pyridin-4-yl)methyl]ethanediamide--3-chlorobenzoic
acid (1/1)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                113.721(3)
_cell_angle_beta                 90.064(2)
_cell_angle_gamma                112.397(3)
_cell_formula_units_Z            2
_cell_length_a                   7.7817(2)
_cell_length_b                   9.5743(3)
_cell_length_c                   11.1516(4)
_cell_measurement_reflns_used    7027
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      75.9960
_cell_measurement_theta_min      5.3620
_cell_volume                     691.47(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
;
<i>SHELXL2017/1</i> (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      100.0(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17474
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.640
_diffrn_reflns_theta_min         4.405
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.535
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.604
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2018)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       rhombohedral
_exptl_crystal_F_000             302
_exptl_crystal_size_max          0.166
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.064
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.467
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2873
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0629P)^2^+0.3630P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1277
_reflns_number_gt                2589
_reflns_number_total             2873
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            wm5558sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        691.47(4)
_cod_database_code               2243397
_cod_database_fobs_code          2243397
_shelx_hkl_checksum              15033
_shelx_res_checksum              34493