#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/01/2230183.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_2230183
loop_
_publ_author_name
'Djamel, Daoud'
'Tahar, Douadi'
'Djahida, Haffar'
'Hanane, Hammani'
'Salah, Chafaa'
_publ_section_title
;
 4,4'-Oxybis{N-[(E)-quinolin-2-ylmethylidene]aniline}
;
_journal_coeditor_code           XU5181
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1119
_journal_page_last               o1120
_journal_paper_doi               10.1107/S1600536811012955
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C32 H22 N4 O'
_chemical_formula_moiety         'C32 H22 N4 O'
_chemical_formula_sum            'C32 H22 N4 O'
_chemical_formula_weight         478.54
_chemical_melting_point          491
_chemical_name_systematic
;
4,4'-Oxybis{N-[(E)-quinolin-2-ylmethylidene]aniline}
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                90
_cell_angle_beta                 92.8390(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.4533(7)
_cell_length_b                   5.0836(2)
_cell_length_c                   26.8170(10)
_cell_measurement_reflns_used    5947
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.34
_cell_volume                     2376.43(16)
_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 1
_diffrn_measured_fraction_theta_max 1
_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  0.0351
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            20425
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.36
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.299
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.1
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0834P)²+0.4121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1499
_reflns_number_gt                4143
_reflns_number_total             5473
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            xu5181.cif
_cod_data_source_block           I
_cod_database_code               2230183
_cod_database_fobs_code          2230183
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_disorder_assembly
_atom_site_disorder_group
N N1 0.44063(7) 0.2230(2) 0.11249(4) 0.0237(3) Uani d . 1 . .
N N4 0.57723(7) -0.2658(2) 0.14573(4) 0.0227(3) Uani d . 1 . .
O O1 0.32016(6) 0.7878(2) -0.05150(4) 0.0302(3) Uani d . 1 . .
C C25 0.49844(8) 0.0726(3) 0.11071(5) 0.0239(3) Uani d . 1 . .
H H25 0.5257 0.0662 0.0818 0.029 Uiso calc R 1 . .
N N3 -0.04347(7) 1.8407(3) -0.14217(5) 0.0282(3) Uani d . 1 . .
C C26 0.52279(8) -0.0916(3) 0.15378(5) 0.0221(3) Uani d . 1 . .
N N2 0.04205(8) 1.3301(3) -0.06988(5) 0.0294(3) Uani d . 1 . .
C C30 0.60189(8) -0.4232(3) 0.18480(5) 0.0220(3) Uani d . 1 . .
C C14 0.25109(8) 0.9214(3) -0.05263(5) 0.0242(3) Uani d . 1 . .
C C22 0.39182(8) 0.4332(3) -0.01897(5) 0.0250(3) Uani d . 1 . .
H H22 0.3994 0.382 -0.0517 0.03 Uiso calc R 1 . .
C C21 0.42483(8) 0.2911(3) 0.02053(5) 0.0250(3) Uani d . 1 . .
H H21 0.4545 0.144 0.0143 0.03 Uiso calc R 1 . .
C C18 0.33675(9) 0.7328(3) 0.03893(6) 0.0259(3) Uani d . 1 . .
H H18 0.3079 0.8823 0.045 0.031 Uiso calc R 1 . .
C C11 0.11440(9) 1.2017(3) -0.06541(5) 0.0258(3) Uani d . 1 . .
C C9 -0.04232(9) 1.6533(3) -0.10785(5) 0.0263(3) Uani d . 1 . .
C C13 0.24528(9) 1.1256(3) -0.08705(6) 0.0271(3) Uani d . 1 . .
H H13 0.2869 1.1686 -0.1058 0.033 Uiso calc R 1 . .
C C6 -0.18146(9) 1.8825(3) -0.13310(6) 0.0269(3) Uani d . 1 . .
C C12 0.17775(9) 1.2639(3) -0.09323(6) 0.0304(4) Uani d . 1 . .
H H12 0.1741 1.4008 -0.1162 0.036 Uiso calc R 1 . .
C C20 0.41394(8) 0.3668(3) 0.06980(5) 0.0216(3) Uani d . 1 . .
C C16 0.12138(9) 0.9950(3) -0.03153(6) 0.0281(3) Uani d . 1 . .
H H16 0.0798 0.9508 -0.0128 0.034 Uiso calc R 1 . .
C C17 0.34752(8) 0.6517(3) -0.00961(5) 0.0234(3) Uani d . 1 . .
C C29 0.57228(8) -0.4008(3) 0.23301(5) 0.0235(3) Uani d . 1 . .
C C10 0.03217(9) 1.5231(3) -0.09934(6) 0.0298(3) Uani d . 1 . .
H H10 0.0738 1.5847 -0.1163 0.036 Uiso calc R 1 . .
C C31 0.65914(9) -0.6133(3) 0.17642(6) 0.0264(3) Uani d . 1 . .
H H31 0.6786 -0.6303 0.1449 0.032 Uiso calc R 1 . .
C C19 0.36957(8) 0.5879(3) 0.07820(5) 0.0247(3) Uani d . 1 . .
H H19 0.3618 0.6396 0.1108 0.03 Uiso calc R 1 . .
C C34 0.60200(9) -0.5671(3) 0.27190(6) 0.0278(3) Uani d . 1 . .
H H34 0.5836 -0.5531 0.3038 0.033 Uiso calc R 1 . .
C C28 0.51373(9) -0.2130(3) 0.23956(6) 0.0269(3) Uani d . 1 . .
H H28 0.4925 -0.1939 0.2705 0.032 Uiso calc R 1 . .
C C1 -0.11244(9) 1.9575(3) -0.15479(5) 0.0260(3) Uani d . 1 . .
C C33 0.65745(9) -0.7475(3) 0.26262(6) 0.0311(4) Uani d . 1 . .
H H33 0.6767 -0.8554 0.2883 0.037 Uiso calc R 1 . .
C C27 0.48872(9) -0.0606(3) 0.20035(5) 0.0258(3) Uani d . 1 . .
H H27 0.4499 0.062 0.204 0.031 Uiso calc R 1 . .
C C15 0.18910(9) 0.8532(3) -0.02517(6) 0.0290(3) Uani d . 1 . .
H H15 0.1928 0.7139 -0.0027 0.035 Uiso calc R 1 . .
C C5 -0.25113(9) 2.0034(3) -0.15027(6) 0.0315(4) Uani d . 1 . .
H H5 -0.2971 1.9519 -0.1371 0.038 Uiso calc R 1 . .
C C32 0.68574(9) -0.7717(3) 0.21458(6) 0.0300(4) Uani d . 1 . .
H H32 0.723 -0.8972 0.2088 0.036 Uiso calc R 1 . .
C C7 -0.17651(9) 1.6876(3) -0.09530(6) 0.0345(4) Uani d . 1 . .
H H7 -0.2201 1.6375 -0.0792 0.041 Uiso calc R 1 . .
C C8 -0.10793(10) 1.5743(3) -0.08275(6) 0.0337(4) Uani d . 1 . .
H H8 -0.1041 1.4464 -0.058 0.04 Uiso calc R 1 . .
C C4 -0.25106(10) 2.1942(4) -0.18585(6) 0.0369(4) Uani d . 1 . .
H H4 -0.297 2.2737 -0.1966 0.044 Uiso calc R 1 . .
C C2 -0.11438(10) 2.1559(3) -0.19178(6) 0.0364(4) Uani d . 1 . .
H H2 -0.0692 2.207 -0.2061 0.044 Uiso calc R 1 . .
C C3 -0.18194(11) 2.2725(4) -0.20663(6) 0.0400(4) Uani d . 1 . .
H H3 -0.1825 2.4047 -0.2306 0.048 Uiso calc R 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 0.0016 '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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C25 N1 C20 . . 120.70(13) ?
C26 N4 C30 . . 117.80(12) ?
C14 O1 C17 . . 121.91(11) ?
N1 C25 C26 . . 120.80(13) ?
N1 C25 H25 . . 119.6 ?
C26 C25 H25 . . 119.6 ?
C9 N3 C1 . . 117.82(13) ?
N4 C26 C27 . . 123.60(13) ?
N4 C26 C25 . . 115.68(13) ?
C27 C26 C25 . . 120.72(13) ?
C10 N2 C11 . . 120.10(14) ?
N4 C30 C31 . . 118.33(13) ?
N4 C30 C29 . . 122.30(13) ?
C31 C30 C29 . . 119.37(13) ?
C15 C14 O1 . . 124.71(13) ?
C15 C14 C13 . . 120.53(14) ?
O1 C14 C13 . . 114.60(13) ?
C17 C22 C21 . . 119.69(13) ?
C17 C22 H22 . . 120.2 ?
C21 C22 H22 . . 120.2 ?
C22 C21 C20 . . 120.59(13) ?
C22 C21 H21 . . 119.7 ?
C20 C21 H21 . . 119.7 ?
C19 C18 C17 . . 119.01(13) ?
C19 C18 H18 . . 120.5 ?
C17 C18 H18 . . 120.5 ?
C16 C11 C12 . . 118.21(14) ?
C16 C11 N2 . . 116.80(14) ?
C12 C11 N2 . . 124.97(14) ?
N3 C9 C8 . . 123.37(14) ?
N3 C9 C10 . . 114.56(14) ?
C8 C9 C10 . . 122.00(14) ?
C12 C13 C14 . . 119.72(14) ?
C12 C13 H13 . . 120.1 ?
C14 C13 H13 . . 120.1 ?
C1 C6 C7 . . 117.34(14) ?
C1 C6 C5 . . 118.88(14) ?
C7 C6 C5 . . 123.78(15) ?
C13 C12 C11 . . 121.00(14) ?
C13 C12 H12 . . 119.5 ?
C11 C12 H12 . . 119.5 ?
C19 C20 C21 . . 118.61(13) ?
C19 C20 N1 . . 116.72(13) ?
C21 C20 N1 . . 124.52(13) ?
C15 C16 C11 . . 121.29(14) ?
C15 C16 H16 . . 119.4 ?
C11 C16 H16 . . 119.4 ?
C22 C17 O1 . . 115.31(13) ?
C22 C17 C18 . . 120.79(13) ?
O1 C17 C18 . . 123.77(13) ?
C28 C29 C30 . . 117.68(13) ?
C28 C29 C34 . . 123.35(14) ?
C30 C29 C34 . . 118.97(14) ?
N2 C10 C9 . . 122.63(15) ?
N2 C10 H10 . . 118.7 ?
C9 C10 H10 . . 118.7 ?
C32 C31 C30 . . 120.01(14) ?
C32 C31 H31 . . 120 ?
C30 C31 H31 . . 120 ?
C18 C19 C20 . . 121.29(13) ?
C18 C19 H19 . . 119.4 ?
C20 C19 H19 . . 119.4 ?
C33 C34 C29 . . 120.17(14) ?
C33 C34 H34 . . 119.9 ?
C29 C34 H34 . . 119.9 ?
C27 C28 C29 . . 119.59(14) ?
C27 C28 H28 . . 120.2 ?
C29 C28 H28 . . 120.2 ?
N3 C1 C2 . . 118.23(14) ?
N3 C1 C6 . . 122.47(14) ?
C2 C1 C6 . . 119.28(14) ?
C34 C33 C32 . . 120.64(14) ?
C34 C33 H33 . . 119.7 ?
C32 C33 H33 . . 119.7 ?
C28 C27 C26 . . 119.00(14) ?
C28 C27 H27 . . 120.5 ?
C26 C27 H27 . . 120.5 ?
C14 C15 C16 . . 119.23(14) ?
C14 C15 H15 . . 120.4 ?
C16 C15 H15 . . 120.4 ?
C4 C5 C6 . . 120.38(16) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C31 C32 C33 . . 120.83(15) ?
C31 C32 H32 . . 119.6 ?
C33 C32 H32 . . 119.6 ?
C8 C7 C6 . . 119.76(15) ?
C8 C7 H7 . . 120.1 ?
C6 C7 H7 . . 120.1 ?
C7 C8 C9 . . 119.14(15) ?
C7 C8 H8 . . 120.4 ?
C9 C8 H8 . . 120.4 ?
C5 C4 C3 . . 120.57(15) ?
C5 C4 H4 . . 119.7 ?
C3 C4 H4 . . 119.7 ?
C3 C2 C1 . . 120.41(16) ?
C3 C2 H2 . . 119.8 ?
C1 C2 H2 . . 119.8 ?
C2 C3 C4 . . 120.44(16) ?
C2 C3 H3 . . 119.8 ?
C4 C3 H3 . . 119.8 ?
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 C25 . 1.2686(18) ?
N1 C20 . 1.4177(18) ?
N4 C26 . 1.3241(18) ?
N4 C30 . 1.3706(18) ?
O1 C14 . 1.3828(18) ?
O1 C17 . 1.3841(17) ?
C25 C26 . 1.471(2) ?
C25 H25 . 0.93 ?
N3 C9 . 1.3240(19) ?
N3 C1 . 1.3697(19) ?
C26 C27 . 1.418(2) ?
N2 C10 . 1.266(2) ?
N2 C11 . 1.4213(19) ?
C30 C31 . 1.416(2) ?
C30 C29 . 1.420(2) ?
C14 C15 . 1.383(2) ?
C14 C13 . 1.389(2) ?
C22 C17 . 1.384(2) ?
C22 C21 . 1.384(2) ?
C22 H22 . 0.93 ?
C21 C20 . 1.398(2) ?
C21 H21 . 0.93 ?
C18 C19 . 1.386(2) ?
C18 C17 . 1.387(2) ?
C18 H18 . 0.93 ?
C11 C16 . 1.391(2) ?
C11 C12 . 1.400(2) ?
C9 C8 . 1.415(2) ?
C9 C10 . 1.467(2) ?
C13 C12 . 1.375(2) ?
C13 H13 . 0.93 ?
C6 C1 . 1.416(2) ?
C6 C7 . 1.417(2) ?
C6 C5 . 1.419(2) ?
C12 H12 . 0.93 ?
C20 C19 . 1.389(2) ?
C16 C15 . 1.388(2) ?
C16 H16 . 0.93 ?
C29 C28 . 1.416(2) ?
C29 C34 . 1.421(2) ?
C10 H10 . 0.93 ?
C31 C32 . 1.365(2) ?
C31 H31 . 0.93 ?
C19 H19 . 0.93 ?
C34 C33 . 1.365(2) ?
C34 H34 . 0.93 ?
C28 C27 . 1.361(2) ?
C28 H28 . 0.93 ?
C1 C2 . 1.414(2) ?
C33 C32 . 1.408(2) ?
C33 H33 . 0.93 ?
C27 H27 . 0.93 ?
C15 H15 . 0.93 ?
C5 C4 . 1.361(2) ?
C5 H5 . 0.93 ?
C32 H32 . 0.93 ?
C7 C8 . 1.355(2) ?
C7 H7 . 0.93 ?
C8 H8 . 0.93 ?
C4 C3 . 1.411(3) ?
C4 H4 . 0.93 ?
C2 C3 . 1.362(2) ?
C2 H2 . 0.93 ?
C3 H3 . 0.93 ?
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
C28 H28 N3 4_676 0.93 2.57 3.434(2) 156
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656673
