#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/03/2230319.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_2230319
loop_
_publ_author_name
'Djamel, Daoud'
'Tahar, Douadi'
'Djahida, Haffar'
'Hanane, Hammani'
'Salah, Chafaa'
_publ_section_title
;
 4,4'-Methylenebis{N-[(E)-quinolin-2-ylmethylidene]aniline}
;
_journal_coeditor_code           FY2004
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1318
_journal_paper_doi               10.1107/S1600536811016011
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C33 H24 N4'
_chemical_formula_moiety         'C33 H24 N4'
_chemical_formula_sum            'C33 H24 N4'
_chemical_formula_weight         476.56
_chemical_melting_point          472
_chemical_name_systematic
;
4,4'-Methylenebis{N-[(E)-quinolin-2-ylmethylidene]aniline}
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                88.393(2)
_cell_angle_beta                 88.521(2)
_cell_angle_gamma                78.044(2)
_cell_formula_units_Z            1
_cell_length_a                   4.6051(2)
_cell_length_b                   6.0189(2)
_cell_length_c                   22.2172(8)
_cell_measurement_reflns_used    3977
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      2.75
_cell_volume                     602.09(4)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'APEX2 (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9094
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         3.46
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             250
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         2707
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0373P)²+0.1098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0867
_reflns_number_gt                2415
_reflns_number_total             2707
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fy2004.cif
_cod_data_source_block           I
_cod_database_code               2230319
_cod_database_fobs_code          2230319
loop_
_space_group_symop_operation_xyz
'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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.6501(4) 0.5318(3) 0.77370(8) 0.0237(4) Uani d . 1 1 . .
N N2 1.0442(4) 0.6798(3) 0.89610(8) 0.0238(4) Uani d . 1 1 . .
N N4 1.0206(4) -0.2145(3) 1.38522(9) 0.0268(4) Uani d . 1 1 . .
C C5 0.2926(5) 0.8583(4) 0.73373(10) 0.0253(5) Uani d . 1 1 . .
C C10 0.9472(5) 0.5623(4) 0.85769(10) 0.0247(5) Uani d . 1 1 . .
H H10 1.0207 0.4063 0.8569 0.03 Uiso calc R 1 1 . .
C C24 1.3130(5) -0.1462(4) 1.29921(10) 0.0278(5) Uani d . 1 1 . .
H H24 1.2005 0.0007 1.2957 0.033 Uiso calc R 1 1 . .
C C17 1.9310(5) 0.3232(4) 1.07135(10) 0.0269(5) Uani d . 1 1 . .
H H17A 1.9971 0.4504 1.0884 0.032 Uiso calc R 1 1 . .
H H17B 2.1015 0.2279 1.052 0.032 Uiso calc R 1 1 . .
N N3 1.5292(4) -0.2108(3) 1.26316(8) 0.0276(4) Uani d . 1 1 . .
C C21 1.6114(5) -0.0656(4) 1.21714(10) 0.0253(5) Uani d . 1 1 . .
C C29 0.9465(5) -0.3569(4) 1.42954(10) 0.0248(5) Uani d . 1 1 . .
C C9 0.7206(5) 0.6683(4) 0.81435(10) 0.0228(5) Uani d . 1 1 . .
C C12 1.3477(5) 0.7218(4) 0.97880(10) 0.0258(5) Uani d . 1 1 . .
H H12 1.2586 0.8754 0.9777 0.031 Uiso calc R 1 1 . .
C C6 0.4393(5) 0.6264(4) 0.73269(10) 0.0228(5) Uani d . 1 1 . .
C C11 1.2656(4) 0.5772(4) 0.93764(9) 0.0219(5) Uani d . 1 1 . .
C C25 1.2375(5) -0.3021(4) 1.34684(10) 0.0258(5) Uani d . 1 1 . .
C C16 1.4071(5) 0.3483(4) 0.93972(10) 0.0251(5) Uani d . 1 1 . .
H H16 1.3565 0.2488 0.9125 0.03 Uiso calc R 1 1 . .
C C28 1.0849(5) -0.5901(4) 1.43483(10) 0.0265(5) Uani d . 1 1 . .
C C15 1.6231(5) 0.2676(4) 0.98216(10) 0.0250(5) Uani d . 1 1 . .
H H15 1.7168 0.1151 0.9826 0.03 Uiso calc R 1 1 . .
C C22 1.8462(5) -0.1645(4) 1.17962(10) 0.0272(5) Uani d . 1 1 . .
H H22 1.9367 -0.3162 1.1859 0.033 Uiso calc R 1 1 . .
C C4 0.0736(5) 0.9418(4) 0.69045(11) 0.0327(5) Uani d . 1 1 . .
H H4 -0.0249 1.0932 0.6911 0.039 Uiso calc R 1 1 . .
C C7 0.3754(5) 0.9952(4) 0.77817(10) 0.0296(5) Uani d . 1 1 . .
H H7 0.2831 1.1476 0.7804 0.035 Uiso calc R 1 1 . .
C C8 0.5909(5) 0.9030(4) 0.81772(10) 0.0267(5) Uani d . 1 1 . .
H H8 0.6519 0.9923 0.8464 0.032 Uiso calc R 1 1 . .
C C13 1.5611(5) 0.6402(4) 1.02157(10) 0.0262(5) Uani d . 1 1 . .
H H13 1.611 0.7397 1.0489 0.031 Uiso calc R 1 1 . .
C C33 0.9868(5) -0.7265(4) 1.48092(11) 0.0309(5) Uani d . 1 1 . .
H H33 1.0742 -0.88 1.4843 0.037 Uiso calc R 1 1 . .
C C32 0.7644(6) -0.6344(4) 1.52053(11) 0.0340(6) Uani d . 1 1 . .
H H32 0.702 -0.7254 1.5506 0.041 Uiso calc R 1 1 . .
C C30 0.7182(5) -0.2664(4) 1.47154(11) 0.0301(5) Uani d . 1 1 . .
H H30 0.6277 -0.1134 1.4689 0.036 Uiso calc R 1 1 . .
C C1 0.3662(5) 0.4863(4) 0.68751(10) 0.0272(5) Uani d . 1 1 . .
H H1 0.4637 0.3349 0.6857 0.033 Uiso calc R 1 1 . .
C C14 1.7009(5) 0.4130(4) 1.02415(10) 0.0237(5) Uani d . 1 1 . .
C C19 1.5822(5) 0.2860(4) 1.15999(10) 0.0273(5) Uani d . 1 1 . .
H H19 1.4927 0.438 1.1537 0.033 Uiso calc R 1 1 . .
C C23 1.9483(5) -0.0403(4) 1.13279(11) 0.0286(5) Uani d . 1 1 . .
H H23 2.1062 -0.1098 1.1083 0.034 Uiso calc R 1 1 . .
C C3 0.0056(5) 0.8029(5) 0.64793(12) 0.0359(6) Uani d . 1 1 . .
H H3 -0.1385 0.8601 0.6198 0.043 Uiso calc R 1 1 . .
C C2 0.1522(5) 0.5731(4) 0.64641(11) 0.0322(5) Uani d . 1 1 . .
H H2 0.1037 0.4795 0.6173 0.039 Uiso calc R 1 1 . .
C C18 1.8167(5) 0.1865(4) 1.12220(10) 0.0240(5) Uani d . 1 1 . .
C C27 1.3166(5) -0.6745(4) 1.39298(10) 0.0304(5) Uani d . 1 1 . .
H H27 1.4141 -0.826 1.3951 0.036 Uiso calc R 1 1 . .
C C26 1.3957(5) -0.5313(4) 1.34953(10) 0.0287(5) Uani d . 1 1 . .
H H26 1.5499 -0.583 1.3223 0.034 Uiso calc R 1 1 . .
C C20 1.4791(5) 0.1629(4) 1.20683(10) 0.0276(5) Uani d . 1 1 . .
H H20 1.3218 0.2326 1.2314 0.033 Uiso calc R 1 1 . .
C C31 0.6299(5) -0.4020(4) 1.51582(11) 0.0333(5) Uani d . 1 1 . .
H H31 0.4799 -0.3404 1.543 0.04 Uiso calc R 1 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0 '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
C9 N1 C6 . . 117.22(19) ?
C10 N2 C11 . . 121.13(17) ?
C25 N4 C29 . . 117.13(19) ?
C7 C5 C4 . . 123.2(2) ?
C7 C5 C6 . . 117.7(2) ?
C4 C5 C6 . . 119.1(2) ?
N2 C10 C9 . . 121.21(18) ?
N2 C10 H10 . . 119.4 ?
C9 C10 H10 . . 119.4 ?
N3 C24 C25 . . 120.6(2) ?
N3 C24 H24 . . 119.7 ?
C25 C24 H24 . . 119.7 ?
C14 C17 C18 . . 113.55(17) ?
C14 C17 H17A . . 108.9 ?
C18 C17 H17A . . 108.9 ?
C14 C17 H17B . . 108.9 ?
C18 C17 H17B . . 108.9 ?
H17A C17 H17B . . 107.7 ?
C24 N3 C21 . . 122.4(2) ?
C22 C21 C20 . . 118.4(2) ?
C22 C21 N3 . . 115.5(2) ?
C20 C21 N3 . . 126.1(2) ?
N4 C29 C30 . . 118.1(2) ?
N4 C29 C28 . . 123.1(2) ?
C30 C29 C28 . . 118.8(2) ?
N1 C9 C8 . . 124.0(2) ?
N1 C9 C10 . . 116.01(18) ?
C8 C9 C10 . . 120.03(18) ?
C13 C12 C11 . . 121.0(2) ?
C13 C12 H12 . . 119.5 ?
C11 C12 H12 . . 119.5 ?
N1 C6 C5 . . 122.56(19) ?
N1 C6 C1 . . 118.5(2) ?
C5 C6 C1 . . 118.9(2) ?
C12 C11 C16 . . 118.22(19) ?
C12 C11 N2 . . 115.96(19) ?
C16 C11 N2 . . 125.81(18) ?
N4 C25 C26 . . 124.0(2) ?
N4 C25 C24 . . 116.30(19) ?
C26 C25 C24 . . 119.7(2) ?
C15 C16 C11 . . 120.7(2) ?
C15 C16 H16 . . 119.7 ?
C11 C16 H16 . . 119.7 ?
C27 C28 C33 . . 123.3(2) ?
C27 C28 C29 . . 117.5(2) ?
C33 C28 C29 . . 119.2(2) ?
C16 C15 C14 . . 120.9(2) ?
C16 C15 H15 . . 119.6 ?
C14 C15 H15 . . 119.6 ?
C21 C22 C23 . . 121.1(2) ?
C21 C22 H22 . . 119.4 ?
C23 C22 H22 . . 119.4 ?
C3 C4 C5 . . 120.8(2) ?
C3 C4 H4 . . 119.6 ?
C5 C4 H4 . . 119.6 ?
C8 C7 C5 . . 119.7(2) ?
C8 C7 H7 . . 120.1 ?
C5 C7 H7 . . 120.1 ?
C7 C8 C9 . . 118.8(2) ?
C7 C8 H8 . . 120.6 ?
C9 C8 H8 . . 120.6 ?
C14 C13 C12 . . 121.1(2) ?
C14 C13 H13 . . 119.4 ?
C12 C13 H13 . . 119.4 ?
C32 C33 C28 . . 120.6(2) ?
C32 C33 H33 . . 119.7 ?
C28 C33 H33 . . 119.7 ?
C33 C32 C31 . . 120.2(2) ?
C33 C32 H32 . . 119.9 ?
C31 C32 H32 . . 119.9 ?
C31 C30 C29 . . 120.7(2) ?
C31 C30 H30 . . 119.7 ?
C29 C30 H30 . . 119.7 ?
C2 C1 C6 . . 120.3(2) ?
C2 C1 H1 . . 119.8 ?
C6 C1 H1 . . 119.8 ?
C13 C14 C15 . . 118.2(2) ?
C13 C14 C17 . . 121.1(2) ?
C15 C14 C17 . . 120.7(2) ?
C20 C19 C18 . . 121.4(2) ?
C20 C19 H19 . . 119.3 ?
C18 C19 H19 . . 119.3 ?
C18 C23 C22 . . 120.7(2) ?
C18 C23 H23 . . 119.7 ?
C22 C23 H23 . . 119.7 ?
C4 C3 C2 . . 120.4(2) ?
C4 C3 H3 . . 119.8 ?
C2 C3 H3 . . 119.8 ?
C1 C2 C3 . . 120.5(2) ?
C1 C2 H2 . . 119.7 ?
C3 C2 H2 . . 119.7 ?
C23 C18 C19 . . 118.2(2) ?
C23 C18 C17 . . 120.7(2) ?
C19 C18 C17 . . 121.1(2) ?
C26 C27 C28 . . 119.5(2) ?
C26 C27 H27 . . 120.2 ?
C28 C27 H27 . . 120.2 ?
C27 C26 C25 . . 118.7(2) ?
C27 C26 H26 . . 120.6 ?
C25 C26 H26 . . 120.6 ?
C19 C20 C21 . . 120.2(2) ?
C19 C20 H20 . . 119.9 ?
C21 C20 H20 . . 119.9 ?
C30 C31 C32 . . 120.5(2) ?
C30 C31 H31 . . 119.7 ?
C32 C31 H31 . . 119.7 ?
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
N1 C9 . 1.328(3) ?
N1 C6 . 1.373(3) ?
N2 C10 . 1.270(3) ?
N2 C11 . 1.424(3) ?
N4 C25 . 1.329(3) ?
N4 C29 . 1.370(3) ?
C5 C7 . 1.412(3) ?
C5 C4 . 1.417(3) ?
C5 C6 . 1.420(3) ?
C10 C9 . 1.471(3) ?
C10 H10 . 0.93 ?
C24 N3 . 1.265(3) ?
C24 C25 . 1.477(3) ?
C24 H24 . 0.93 ?
C17 C14 . 1.517(3) ?
C17 C18 . 1.526(3) ?
C17 H17A . 0.97 ?
C17 H17B . 0.97 ?
N3 C21 . 1.421(3) ?
C21 C22 . 1.390(3) ?
C21 C20 . 1.399(3) ?
C29 C30 . 1.419(3) ?
C29 C28 . 1.419(3) ?
C9 C8 . 1.418(3) ?
C12 C13 . 1.390(3) ?
C12 C11 . 1.392(3) ?
C12 H12 . 0.93 ?
C6 C1 . 1.419(3) ?
C11 C16 . 1.397(3) ?
C25 C26 . 1.421(3) ?
C16 C15 . 1.392(3) ?
C16 H16 . 0.93 ?
C28 C27 . 1.418(3) ?
C28 C33 . 1.418(3) ?
C15 C14 . 1.399(3) ?
C15 H15 . 0.93 ?
C22 C23 . 1.393(3) ?
C22 H22 . 0.93 ?
C4 C3 . 1.363(4) ?
C4 H4 . 0.93 ?
C7 C8 . 1.362(3) ?
C7 H7 . 0.93 ?
C8 H8 . 0.93 ?
C13 C14 . 1.386(3) ?
C13 H13 . 0.93 ?
C33 C32 . 1.370(4) ?
C33 H33 . 0.93 ?
C32 C31 . 1.409(4) ?
C32 H32 . 0.93 ?
C30 C31 . 1.368(3) ?
C30 H30 . 0.93 ?
C1 C2 . 1.373(3) ?
C1 H1 . 0.93 ?
C19 C20 . 1.391(3) ?
C19 C18 . 1.394(3) ?
C19 H19 . 0.93 ?
C23 C18 . 1.390(3) ?
C23 H23 . 0.93 ?
C3 C2 . 1.408(4) ?
C3 H3 . 0.93 ?
C2 H2 . 0.93 ?
C27 C26 . 1.368(3) ?
C27 H27 . 0.93 ?
C26 H26 . 0.93 ?
C20 H20 . 0.93 ?
C31 H31 . 0.93 ?
