#------------------------------------------------------------------------------
#$Date: 2019-12-25 21:36:07 +0200 (Wed, 25 Dec 2019) $
#$Revision: 245754 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/12/2311281.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_2311281
loop_
_publ_author_name
'Abdoh, Muneer'
'Warad, Ismail'
'Naveen, S.'
'Lokanath, N. K.'
'Salghi, Rachid'
_publ_section_title
;
 Crystal structure of
 (1E,1'E)-N,N'-(ethane-1,2-di-yl)bis-[(pyridin-2-yl)methanimine].
;
_journal_coeditor_code           SU5142
_journal_issue                   'Pt 6'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              o431
_journal_paper_doi               10.1107/S2056989015010087
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C14 H14 N4'
_chemical_formula_moiety         'C14 H14 N4'
_chemical_formula_sum            'C14 H14 N4'
_chemical_formula_weight         238.29
_chemical_name_systematic
(1E,1'E)-N,N'-(Ethane-1,2-diyl)bis[(pyridin-2-yl)methanimine]
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 122.266(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.347(5)
_cell_length_b                   5.9339(12)
_cell_length_c                   13.165(2)
_cell_measurement_reflns_used    881
_cell_measurement_temperature    296
_cell_measurement_theta_max      63.82
_cell_measurement_theta_min      5.41
_cell_volume                     1278.0(5)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 18.4
_diffrn_measured_fraction_theta_full 0.883
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_device_type  'Bruker X8 Proteum'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            1539
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        63.82
_diffrn_reflns_theta_max         63.82
_diffrn_reflns_theta_min         5.41
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.098
_refine_diff_density_min         -0.097
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0763P)²+0.2763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1203
_reflns_number_gt                881
_reflns_number_total             933
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su5142sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2311281
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,1/2+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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
N N3 0.69126(7) 0.50665(18) 0.02615(10) 0.0576(4) Uani d . 1.000
N N6 0.55349(7) 0.05345(19) -0.11311(9) 0.0542(4) Uani d . 1.000
C C1 0.67191(10) 0.7085(3) 0.16610(14) 0.0703(6) Uani d . 1.000
C C2 0.70819(9) 0.6792(2) 0.10143(14) 0.0634(5) Uani d . 1.000
C C4 0.63482(8) 0.3583(2) 0.01373(11) 0.0478(4) Uani d . 1.000
C C5 0.61592(8) 0.1747(2) -0.07264(11) 0.0495(4) Uani d . 1.000
C C7 0.54261(9) -0.1287(2) -0.19397(13) 0.0585(5) Uani d . 1.000
C C8 0.59615(9) 0.3750(2) 0.07686(12) 0.0591(5) Uani d . 1.000
C C9 0.61501(11) 0.5541(3) 0.15343(14) 0.0728(6) Uani d . 1.000
H H1 0.68570 0.83080 0.21760 0.0840 Uiso c R 1.000
H H2 0.55830 0.26720 0.06750 0.0710 Uiso c R 1.000
H H4 0.74660 0.78490 0.11040 0.0760 Uiso c R 1.000
H H5 0.65170 0.14760 -0.09810 0.0590 Uiso c R 1.000
H H7 0.58250 -0.11360 -0.21680 0.0700 Uiso c R 1.000
H H8 0.55230 -0.27160 -0.15260 0.0700 Uiso c R 1.000
H H9 0.58950 0.57050 0.19620 0.0870 Uiso c R 1.000
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'
N N 0.0311 0.0180 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C2 N3 C4 . . 116.96(15) no
C5 N6 C7 . . 117.93(15) no
C2 C1 C9 . . 118.85(16) no
N3 C2 C1 . . 123.50(16) no
N3 C4 C5 . . 115.43(14) no
N3 C4 C8 . . 122.94(12) no
C5 C4 C8 . . 121.62(13) no
N6 C5 C4 . . 122.55(15) no
N6 C7 C7 . 2_654 111.74(13) no
C4 C8 C9 . . 118.56(16) no
C1 C9 C8 . . 119.17(19) no
C2 C1 H1 . . 121.00 no
C9 C1 H1 . . 121.00 no
N3 C2 H4 . . 118.00 no
C1 C2 H4 . . 118.00 no
N6 C5 H5 . . 119.00 no
C4 C5 H5 . . 119.00 no
N6 C7 H7 . . 109.00 no
N6 C7 H8 . . 109.00 no
H7 C7 H8 . . 108.00 no
C7 C7 H7 2_654 . 109.00 no
C7 C7 H8 2_654 . 109.00 no
C4 C8 H2 . . 121.00 no
C9 C8 H2 . . 121.00 no
C1 C9 H9 . . 120.00 no
C8 C9 H9 . . 120.00 no
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
N3 C2 . 1.3384(18) no
N3 C4 . 1.343(2) no
N6 C5 . 1.254(2) no
N6 C7 . 1.4514(18) no
C1 C2 . 1.373(3) no
C1 C9 . 1.372(3) no
C4 C5 . 1.4730(18) no
C4 C8 . 1.387(2) no
C7 C7 2_654 1.516(2) no
C8 C9 . 1.373(2) no
C1 H1 . 0.9300 no
C2 H4 . 0.9300 no
C5 H5 . 0.9300 no
C7 H7 . 0.9700 no
C7 H8 . 0.9700 no
C8 H2 . 0.9300 no
C9 H9 . 0.9300 no
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_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N3 C4 C5 . . 178.17(12) no
C2 N3 C4 C8 . . -1.6(2) no
C4 N3 C2 C1 . . 0.9(2) no
C7 N6 C5 C4 . . -177.50(11) no
C5 N6 C7 C7 . 2_654 -131.18(14) no
C9 C1 C2 N3 . . -0.2(3) no
C2 C1 C9 C8 . . 0.1(3) no
N3 C4 C5 N6 . . -164.26(12) no
C5 C4 C8 C9 . . -178.16(14) no
C8 C4 C5 N6 . . 15.5(2) no
N3 C4 C8 C9 . . 1.6(2) no
N6 C7 C7 N6 2_654 2_654 73.41(17) no
C4 C8 C9 C1 . . -0.8(2) no
