#------------------------------------------------------------------------------
#$Date: 2020-05-20 08:05:43 +0300 (Wed, 20 May 2020) $
#$Revision: 252207 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/33/2243397.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243397
loop_
_publ_author_name
'Tan, Sang Loon'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Crystal structure, Hirshfeld surface analysis and computational study of
 the 1:2 co-crystal formed between
 N,N'-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
;
N,N'-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
;
SHELXL2017/1 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2015a)
;
_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       'ω 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/[σ²(Fo²)+(0.0629P)²+0.3630P] where P=(Fo²+2Fc²)/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 > 2σ(I)'
_cod_data_source_file            wm5558sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        691.47(4)
_cod_database_code               2243397
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Cl Cl1 1.16272(7) 1.19147(7) 0.97323(5) 0.04950(19) Uani d 1 . .
O O2 0.52027(18) 0.7929(2) 0.61549(14) 0.0462(4) Uani d 1 . .
O O3 0.61166(18) 0.70870(18) 0.41896(13) 0.0379(3) Uani d 1 . .
H H3O 0.4966(19) 0.676(4) 0.389(3) 0.080(10) Uiso d 1 . .
C C8 0.6450(2) 0.7875(2) 0.54909(18) 0.0323(4) Uani d 1 . .
C C9 0.8502(2) 0.8715(2) 0.61122(18) 0.0314(4) Uani d 1 . .
C C10 0.9858(3) 0.8450(2) 0.5341(2) 0.0337(4) Uani d 1 . .
H H10 0.949112 0.774182 0.441116 0.040 Uiso calc 1 . .
C C11 1.1744(3) 0.9230(3) 0.5943(2) 0.0383(4) Uani d 1 . .
H H11 1.266423 0.903127 0.542180 0.046 Uiso calc 1 . .
C C12 1.2306(3) 1.0291(3) 0.7289(2) 0.0385(4) Uani d 1 . .
H H12 1.360150 1.082595 0.769580 0.046 Uiso calc 1 . .
C C13 1.0942(3) 1.0560(2) 0.8034(2) 0.0358(4) Uani d 1 . .
C C14 0.9041(2) 0.9776(2) 0.74687(19) 0.0341(4) Uani d 1 . .
H H14 0.812284 0.996077 0.799770 0.041 Uiso calc 1 . .
O O1 0.62312(17) 0.12645(16) -0.07710(13) 0.0330(3) Uani d 1 . .
N N1 1.2621(2) 0.5924(2) 0.31316(17) 0.0383(4) Uani d 1 . .
N N2 0.5685(2) 0.2032(2) 0.13447(16) 0.0328(3) Uani d 1 . .
H H2N 0.522(3) 0.167(3) 0.1913(19) 0.045(7) Uiso d 1 . .
C C1 1.1930(3) 0.6341(3) 0.22886(19) 0.0388(4) Uani d 1 . .
H H1 1.278903 0.712666 0.201889 0.047 Uiso calc 1 . .
C C2 1.0017(3) 0.5676(2) 0.17938(19) 0.0365(4) Uani d 1 . .
H H2 0.958087 0.600506 0.119978 0.044 Uiso calc 1 . .
C C3 0.8745(3) 0.4522(2) 0.21761(18) 0.0339(4) Uani d 1 . .
C C4 0.9465(3) 0.4093(3) 0.3046(2) 0.0444(5) Uani d 1 . .
H H4 0.863962 0.330319 0.332615 0.053 Uiso calc 1 . .
C C5 1.1384(3) 0.4818(3) 0.3502(2) 0.0459(5) Uani d 1 . .
H H5 1.185252 0.452059 0.410711 0.055 Uiso calc 1 . .
C C6 0.6630(3) 0.3820(2) 0.1718(2) 0.0381(4) Uani d 1 . .
H H6A 0.608278 0.441956 0.244426 0.046 Uiso calc 1 . .
H H6B 0.639555 0.402602 0.094503 0.046 Uiso calc 1 . .
C C7 0.5558(2) 0.0917(2) 0.01203(17) 0.0291(4) Uani d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -3 5 0.0471
1 -3 5 0.0318
0 -4 5 0.0304
0 4 -5 0.0338
-2 3 -5 0.0267
0 2 1 0.0334
-3 4 3 0.0354
-4 2 3 0.0571
3 -4 -3 0.0355
1 -4 -2 0.0338
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
C8 O3 H3O . . 110(2) ?
O2 C8 O3 . . 123.38(17) ?
O2 C8 C9 . . 122.38(17) ?
O3 C8 C9 . . 114.23(15) ?
C10 C9 C8 . . 120.62(17) ?
C14 C9 C8 . . 119.03(16) ?
C14 C9 C10 . . 120.35(17) ?
C9 C10 H10 . . 120.3 ?
C11 C10 C9 . . 119.44(19) ?
C11 C10 H10 . . 120.3 ?
C10 C11 H11 . . 119.5 ?
C12 C11 C10 . . 121.04(18) ?
C12 C11 H11 . . 119.5 ?
C11 C12 H12 . . 120.7 ?
C11 C12 C13 . . 118.63(17) ?
C13 C12 H12 . . 120.7 ?
C12 C13 Cl1 . . 119.31(15) ?
C14 C13 Cl1 . . 118.88(15) ?
C14 C13 C12 . . 121.81(19) ?
C9 C14 H14 . . 120.6 ?
C13 C14 C9 . . 118.72(18) ?
C13 C14 H14 . . 120.6 ?
C5 N1 C1 . . 117.60(17) ?
C6 N2 H2N . . 120.9(16) ?
C7 N2 H2N . . 118.3(16) ?
C7 N2 C6 . . 120.72(16) ?
N1 C1 H1 . . 118.6 ?
N1 C1 C2 . . 122.84(17) ?
C2 C1 H1 . . 118.6 ?
C1 C2 H2 . . 120.4 ?
C1 C2 C3 . . 119.22(18) ?
C3 C2 H2 . . 120.4 ?
C2 C3 C6 . . 121.38(18) ?
C4 C3 C2 . . 117.76(17) ?
C4 C3 C6 . . 120.78(17) ?
C3 C4 H4 . . 120.2 ?
C5 C4 C3 . . 119.60(18) ?
C5 C4 H4 . . 120.2 ?
N1 C5 C4 . . 122.98(19) ?
N1 C5 H5 . . 118.5 ?
C4 C5 H5 . . 118.5 ?
N2 C6 C3 . . 112.60(16) ?
N2 C6 H6A . . 109.1 ?
N2 C6 H6B . . 109.1 ?
C3 C6 H6A . . 109.1 ?
C3 C6 H6B . . 109.1 ?
H6A C6 H6B . . 107.8 ?
O1 C7 N2 . . 124.94(17) ?
O1 C7 C7 . 2_655 121.2(2) ?
N2 C7 C7 . 2_655 113.87(19) ?
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
Cl1 C13 . 1.746(2) ?
O2 C8 . 1.225(2) ?
O3 H3O . 0.846(10) ?
O3 C8 . 1.308(2) ?
C8 C9 . 1.499(2) ?
C9 C10 . 1.395(3) ?
C9 C14 . 1.391(3) ?
C10 H10 . 0.9500 ?
C10 C11 . 1.386(3) ?
C11 H11 . 0.9500 ?
C11 C12 . 1.382(3) ?
C12 H12 . 0.9500 ?
C12 C13 . 1.386(3) ?
C13 C14 . 1.386(3) ?
C14 H14 . 0.9500 ?
O1 C7 . 1.228(2) ?
N1 C1 . 1.340(3) ?
N1 C5 . 1.340(3) ?
N2 H2N . 0.857(10) ?
N2 C6 . 1.453(2) ?
N2 C7 . 1.326(2) ?
C1 H1 . 0.9500 ?
C1 C2 . 1.385(3) ?
C2 H2 . 0.9500 ?
C2 C3 . 1.389(3) ?
C3 C4 . 1.385(3) ?
C3 C6 . 1.517(3) ?
C4 H4 . 0.9500 ?
C4 C5 . 1.376(3) ?
C5 H5 . 0.9500 ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C7 2_655 1.539(3) ?
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_655 0.86(2) 2.34(3) 2.717(2) 106.7(17)
N2 H2N O2 2_666 0.86(2) 2.08(2) 2.863(2) 151(2)
O3 H3O N1 1_455 0.84(2) 1.74(2) 2.581(2) 174(4)
C14 H14 O1 1_566 0.95 2.37 3.286(2) 161
C1 H1 O1 2_765 0.95 2.39 3.286(3) 157
C12 H12 O1 1_666 0.95 2.46 3.328(3) 152
C6 H6A O3 1_555 0.99 2.50 3.400(3) 151
C13 Cl1 Cg1 . 1.746(2) 3.8297(10) 5.358(2) 145.33(8)
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
Cl1 C13 C14 C9 . . . . 179.18(14) ?
O2 C8 C9 C10 . . . . 171.79(19) ?
O2 C8 C9 C14 . . . . -8.8(3) ?
O3 C8 C9 C10 . . . . -8.1(2) ?
O3 C8 C9 C14 . . . . 171.32(17) ?
C8 C9 C10 C11 . . . . -179.40(17) ?
C8 C9 C14 C13 . . . . -179.43(17) ?
C9 C10 C11 C12 . . . . -1.3(3) ?
C10 C9 C14 C13 . . . . 0.0(3) ?
C10 C11 C12 C13 . . . . 0.3(3) ?
C11 C12 C13 Cl1 . . . . -179.29(15) ?
C11 C12 C13 C14 . . . . 1.0(3) ?
C12 C13 C14 C9 . . . . -1.1(3) ?
C14 C9 C10 C11 . . . . 1.2(3) ?
N1 C1 C2 C3 . . . . -0.2(3) ?
C1 N1 C5 C4 . . . . 0.7(3) ?
C1 C2 C3 C4 . . . . 0.1(3) ?
C1 C2 C3 C6 . . . . 176.96(19) ?
C2 C3 C4 C5 . . . . 0.4(3) ?
C2 C3 C6 N2 . . . . 138.48(19) ?
C3 C4 C5 N1 . . . . -0.8(4) ?
C4 C3 C6 N2 . . . . -44.8(3) ?
C5 N1 C1 C2 . . . . -0.2(3) ?
C6 N2 C7 O1 . . . . 1.8(3) ?
C6 N2 C7 C7 . . . 2_655 -177.61(17) ?
C6 C3 C4 C5 . . . . -176.5(2) ?
C7 N2 C6 C3 . . . . -86.3(2) ?

_cod_database_fobs_code 2243397
