##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'SHELXL-2014/7'
_chemical_name_systematic
;
2-Methylbenzoic acid--\
N,N'-bis(pyridin-4-ylmethyl)ethanediamide (2/1)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H14 N4 O2, 2(C8 H8 O2)'
_chemical_formula_sum     'C30 H30 N4 O6'
_chemical_formula_iupac     'C14 H14 N4 O2, 2C8 H8 O2'
_chemical_formula_weight     542.58
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     6.8948(5)
_cell_length_b     9.7219(5)
_cell_length_c     9.9621(7)
_cell_angle_alpha     82.971(5)
_cell_angle_beta     81.638(6)
_cell_angle_gamma     85.686(5)
_cell_volume     654.58(8)
_cell_formula_units_Z     1
_cell_measurement_reflns_used     3840
_cell_measurement_theta_min     3.53
_cell_measurement_theta_max     29.97
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.210
_exptl_crystal_size_mid     0.150
_exptl_crystal_size_min     0.100
_exptl_crystal_density_diffrn     1.376
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     286
_exptl_absorpt_coefficient_mu     0.097
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2014)
;
_shelx_estimated_absorpt_T_min     0.980
_shelx_estimated_absorpt_T_max     0.990
_exptl_absorpt_correction_T_min     0.57977
_exptl_absorpt_correction_T_max     1.00000
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator     Mirror
_diffrn_measurement_device_type
     'Agilent Technologies SuperNova Dual diffractometer with an Atlas detector'
_diffrn_measurement_method     'ω scan'
_diffrn_detector_area_resol_mean     10.4041
_diffrn_reflns_number     15067
_diffrn_reflns_av_R_equivalents     0.0444
_diffrn_reflns_theta_min     2.991
_diffrn_reflns_theta_max     27.496
_diffrn_reflns_theta_full     27.496
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details     ?
_reflns_number_total     2993
_reflns_number_gt     2358
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0577
_refine_ls_R_factor_gt     0.0406
_refine_ls_wR_factor_gt     0.0942
_refine_ls_wR_factor_ref     0.1060
_refine_ls_goodness_of_fit_ref     1.059
_refine_ls_restrained_S_all     1.059
_refine_ls_number_reflns     2993
_refine_ls_number_parameters     188
_refine_ls_number_restraints     2
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0434P)²+0.2225P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.340
_refine_diff_density_min     -0.231
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlis PRO (Agilent, 2014)
;
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2014)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg,
2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 -0.26845(15) 1.04906(10) 0.41903(10) 0.0202(2) Uani d 1 . .
    N N1 0.10595(19) 0.54943(12) 0.25502(12) 0.0194(3) Uani d 1 . .
    N N2 -0.34990(18) 0.85635(11) 0.56442(12) 0.0157(3) Uani d 1 . .
    H H2N -0.4483(18) 0.8165(15) 0.6161(14) 0.019 Uiso d 1 . .
    C C1 -0.0650(2) 0.71369(13) 0.45691(14) 0.0159(3) Uani d 1 . .
    C C2 0.1324(2) 0.66915(14) 0.44690(15) 0.0183(3) Uani d 1 . .
    H H2 0.2123 0.6945 0.5089 0.022 Uiso calc 1 . .
    C C3 0.2113(2) 0.58766(14) 0.34574(15) 0.0197(3) Uani d 1 . .
    H H3 0.3461 0.5574 0.3403 0.024 Uiso calc 1 . .
    C C4 -0.0837(2) 0.59250(14) 0.26467(15) 0.0205(3) Uani d 1 . .
    H H4 -0.1600 0.5661 0.2009 0.025 Uiso calc 1 . .
    C C5 -0.1746(2) 0.67411(14) 0.36357(15) 0.0182(3) Uani d 1 . .
    H H5 -0.3100 0.7024 0.3672 0.022 Uiso calc 1 . .
    C C6 -0.1494(2) 0.80107(14) 0.57005(14) 0.0165(3) Uani d 1 . .
    H H3A -0.1442 0.7438 0.6589 0.020 Uiso calc 1 . .
    H H3B -0.0648 0.8796 0.5668 0.020 Uiso calc 1 . .
    C C7 -0.3901(2) 0.97768(13) 0.49211(14) 0.0154(3) Uani d 1 . .
    O O2 0.30435(15) 0.41238(10) 0.06130(11) 0.0200(2) Uani d 1 . .
    H H2O 0.242(2) 0.4581(16) 0.1233(15) 0.030 Uiso d 1 . .
    O O3 0.50558(15) 0.34690(10) 0.21737(10) 0.0210(2) Uani d 1 . .
    C C8 0.4571(2) 0.33987(13) 0.10547(14) 0.0160(3) Uani d 1 . .
    C C9 0.5600(2) 0.24530(13) 0.00615(14) 0.0157(3) Uani d 1 . .
    C C10 0.4507(2) 0.19550(14) -0.08313(15) 0.0183(3) Uani d 1 . .
    H H10 0.3160 0.2250 -0.0817 0.022 Uiso calc 1 . .
    C C11 0.5355(2) 0.10374(14) -0.17385(15) 0.0222(3) Uani d 1 . .
    H H11 0.4586 0.0672 -0.2314 0.027 Uiso calc 1 . .
    C C12 0.7337(2) 0.06622(14) -0.17932(15) 0.0220(3) Uani d 1 . .
    H H12 0.7947 0.0059 -0.2432 0.026 Uiso calc 1 . .
    C C13 0.8436(2) 0.11621(14) -0.09211(15) 0.0195(3) Uani d 1 . .
    H H13 0.9800 0.0904 -0.0983 0.023 Uiso calc 1 . .
    C C14 0.7595(2) 0.20349(13) 0.00468(14) 0.0166(3) Uani d 1 . .
    C C15 0.8858(2) 0.24942(15) 0.09983(16) 0.0225(3) Uani d 1 . .
    H H15A 0.8762 0.3510 0.0945 0.034 Uiso calc 1 . .
    H H15B 1.0226 0.2173 0.0735 0.034 Uiso calc 1 . .
    H H15C 0.8409 0.2100 0.1935 0.034 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C7 . 1.2252(17) ?
    N1 C4 . 1.3364(19) ?
    N1 C3 . 1.3401(19) ?
    N2 C7 . 1.3371(17) ?
    N2 C6 . 1.4510(18) ?
    N2 H2N . 0.874(9) ?
    C1 C5 . 1.385(2) ?
    C1 C2 . 1.390(2) ?
    C1 C6 . 1.5166(18) ?
    C2 C3 . 1.3820(19) ?
    C2 H2 . 0.9500 ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.3892(19) ?
    C4 H4 . 0.9500 ?
    C5 H5 . 0.9500 ?
    C6 H3A . 0.9900 ?
    C6 H3B . 0.9900 ?
    C7 C7 2_476 1.536(3) ?
    O2 C8 . 1.3217(17) ?
    O2 H2O . 0.853(9) ?
    O3 C8 . 1.2205(17) ?
    C8 C9 . 1.4994(18) ?
    C9 C10 . 1.396(2) ?
    C9 C14 . 1.403(2) ?
    C10 C11 . 1.385(2) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.383(2) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.384(2) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.3964(19) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.503(2) ?
    C15 H15A . 0.9800 ?
    C15 H15B . 0.9800 ?
    C15 H15C . 0.9800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C4 N1 C3 . . 117.67(12) ?
    C7 N2 C6 . . 121.54(12) ?
    C7 N2 H2N . . 117.2(11) ?
    C6 N2 H2N . . 120.9(11) ?
    C5 C1 C2 . . 117.97(13) ?
    C5 C1 C6 . . 123.56(13) ?
    C2 C1 C6 . . 118.47(13) ?
    C3 C2 C1 . . 119.31(14) ?
    C3 C2 H2 . . 120.3 ?
    C1 C2 H2 . . 120.3 ?
    N1 C3 C2 . . 122.93(14) ?
    N1 C3 H3 . . 118.5 ?
    C2 C3 H3 . . 118.5 ?
    N1 C4 C5 . . 123.05(14) ?
    N1 C4 H4 . . 118.5 ?
    C5 C4 H4 . . 118.5 ?
    C1 C5 C4 . . 119.07(13) ?
    C1 C5 H5 . . 120.5 ?
    C4 C5 H5 . . 120.5 ?
    N2 C6 C1 . . 115.06(12) ?
    N2 C6 H3A . . 108.5 ?
    C1 C6 H3A . . 108.5 ?
    N2 C6 H3B . . 108.5 ?
    C1 C6 H3B . . 108.5 ?
    H3A C6 H3B . . 107.5 ?
    O1 C7 N2 . . 125.26(13) ?
    O1 C7 C7 . 2_476 121.45(15) ?
    N2 C7 C7 . 2_476 113.29(15) ?
    C8 O2 H2O . . 110.8(13) ?
    O3 C8 O2 . . 123.13(12) ?
    O3 C8 C9 . . 123.68(13) ?
    O2 C8 C9 . . 113.16(12) ?
    C10 C9 C14 . . 120.20(12) ?
    C10 C9 C8 . . 118.28(13) ?
    C14 C9 C8 . . 121.48(12) ?
    C11 C10 C9 . . 121.07(14) ?
    C11 C10 H10 . . 119.5 ?
    C9 C10 H10 . . 119.5 ?
    C12 C11 C10 . . 118.97(14) ?
    C12 C11 H11 . . 120.5 ?
    C10 C11 H11 . . 120.5 ?
    C11 C12 C13 . . 120.28(13) ?
    C11 C12 H12 . . 119.9 ?
    C13 C12 H12 . . 119.9 ?
    C12 C13 C14 . . 121.79(14) ?
    C12 C13 H13 . . 119.1 ?
    C14 C13 H13 . . 119.1 ?
    C13 C14 C9 . . 117.56(13) ?
    C13 C14 C15 . . 119.00(13) ?
    C9 C14 C15 . . 123.43(12) ?
    C14 C15 H15A . . 109.5 ?
    C14 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    C14 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C5 C1 C2 C3 . . . . -0.2(2) ?
    C6 C1 C2 C3 . . . . 179.02(12) ?
    C4 N1 C3 C2 . . . . -0.3(2) ?
    C1 C2 C3 N1 . . . . 0.4(2) ?
    C3 N1 C4 C5 . . . . 0.0(2) ?
    C2 C1 C5 C4 . . . . -0.1(2) ?
    C6 C1 C5 C4 . . . . -179.24(12) ?
    N1 C4 C5 C1 . . . . 0.2(2) ?
    C7 N2 C6 C1 . . . . -87.65(15) ?
    C5 C1 C6 N2 . . . . -7.47(19) ?
    C2 C1 C6 N2 . . . . 173.38(12) ?
    C6 N2 C7 O1 . . . . 4.4(2) ?
    C6 N2 C7 C7 . . . 2_476 -175.86(13) ?
    O3 C8 C9 C10 . . . . 150.23(14) ?
    O2 C8 C9 C10 . . . . -27.92(17) ?
    O3 C8 C9 C14 . . . . -27.8(2) ?
    O2 C8 C9 C14 . . . . 154.08(12) ?
    C14 C9 C10 C11 . . . . 0.4(2) ?
    C8 C9 C10 C11 . . . . -177.60(12) ?
    C9 C10 C11 C12 . . . . -2.8(2) ?
    C10 C11 C12 C13 . . . . 2.1(2) ?
    C11 C12 C13 C14 . . . . 0.9(2) ?
    C12 C13 C14 C9 . . . . -3.3(2) ?
    C12 C13 C14 C15 . . . . 177.62(13) ?
    C10 C9 C14 C13 . . . . 2.56(19) ?
    C8 C9 C14 C13 . . . . -179.48(12) ?
    C10 C9 C14 C15 . . . . -178.36(13) ?
    C8 C9 C14 C15 . . . . -0.4(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N2 H2N O1 2_476 0.874(13) 2.313(13) 2.7100(16) 107.7(11)
    O2 H2O N1 . 0.852(15) 1.787(15) 2.6378(16) 178.1(16)
    N2 H2N O3 2_566 0.874(13) 2.166(14) 2.8933(15) 140.4(12)
    C6 H3B O1 2_576 0.99 2.48 3.3461(18) 146
data_global
_journal_date_recd_electronic     2016-02-12
_journal_date_accepted     2016-02-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2016
_journal_volume     72
_journal_issue      3
_journal_page_first     391
_journal_page_last     398
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989016002735
_journal_coeditor_code     HB7566
loop_
    _publ_contact_author_name
    _publ_contact_author_address
    _publ_contact_author_email
    'Edward R.T. Tiekink'
;
Faculty of Science and Technology,
Sunway University,
No.5 Jalan Universiti,
47500 Bandar Sunway,
Selangor Darul Ehsan, Malaysia
;
 edwardt@sunway.edu.my
_publ_contact_author_fax     ' +60 3 7491 8633 '
_publ_contact_author_phone     ' +60 3 7491 7173 '
_publ_section_title
;
A 2:1 co-crystal of 2-methylbenzoic acid and
N,N'-bis(pyridin-4-ylmethyl)ethanediamide: crystal structure and
Hirshfeld surface analysis
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Sabrina Syed' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
    'Jotani, Mukesh M.'
;
Additional correspondence author, e-mail: mmjotani@rediffmail.com.
;
;
Department of Physics, Bhavan's Sheth R. A. College of Science, Ahmedabad,
Gujarat 380 001, India
;
    'Siti Nadiah Abdul Halim' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
    'Tiekink, Edward R. T.' .
;
Centre for Crystalline Materials,
Faculty of Science and Technology,
Sunway University, 47500 Bandar Sunway,
Selangor Darul Ehsan, Malaysia
;
_publ_section_synopsis
;
The 2:1 acid/diamide co-crystal sees the components connected into
three-molecule aggregates via hydroxy-O---H...N(pyridyl) hydrogen
bonds. The aggregates are linked into a supramolecular layer via
amide-N---H...O(carbonyl) and methylene-C---H...O(amide) interactions. The
three-dimensional packing is consolidated by π--π interactions involving all
the aromatic residues.
;
