#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/43/2234364.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_2234364
loop_
_publ_author_name
'Ourari, Ali'
'Baameur, Lotfi'
'Bouet, Gilles'
'Allain, Magali'
_publ_section_title
;
 2-[N-(4-{4-[(2-Hydroxy-5-methoxybenzylidene)amino]benzyl}phenyl)carboximidoyl]-4-methoxyphenol
;
_journal_coeditor_code           QK2024
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1141
_journal_paper_doi               10.1107/S1600536812010550
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C29 H26 N2 O4'
_chemical_formula_moiety         'C29 H26 N2 O4'
_chemical_formula_sum            'C29 H26 N2 O4'
_chemical_formula_weight         466.52
_chemical_name_systematic
;
2-[N-(4-{4-[(2-Hydroxy-5-
methoxybenzylidene)amino]benzyl}phenyl)carboximidoyl]-4-methoxyphenol
;
_space_group_IT_number           15
_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
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90.00
_cell_angle_beta                 93.653(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   41.307(4)
_cell_length_b                   4.5993(3)
_cell_length_c                   12.2229(13)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.9
_cell_measurement_theta_min      1.95
_cell_volume                     2317.4(4)
_computing_cell_refinement       'X-RED (Stoe & Cie, 1995)'
_computing_data_collection       'EXPOSE (Stoe & Cie, 1995)'
_computing_data_reduction        'X-RED (Stoe & Cie, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.66
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       '0.6° φ '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10694
_diffrn_reflns_theta_full        25.94
_diffrn_reflns_theta_max         25.8
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.9529
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(PLATON-ABSGAUSS; Spek, 2009)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.148
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2244
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0720P)²+0.1658P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1163
_reflns_number_gt                1662
_reflns_number_total             2244
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qk2024.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2234364
_cod_database_fobs_code          2234364
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_symmetry_multiplicity
O O1 0.37635(3) 0.9988(3) 0.40329(8) 0.0634(3) Uani d . 1 1
H H1 0.3881 0.8694 0.4423 0.076 Uiso d R 1 1
O O2 0.28937(3) 1.4522(3) 0.68223(9) 0.0651(4) Uani d . 1 1
N N1 0.40032(2) 0.7019(2) 0.57231(8) 0.0404(3) Uani d . 1 1
C C1 0.35488(3) 1.1095(3) 0.47152(10) 0.0435(3) Uani d . 1 1
C C2 0.33158(3) 1.3024(4) 0.43070(11) 0.0521(4) Uani d . 1 1
H H2 0.3309 1.3538 0.3570 0.063 Uiso calc R 1 1
C C3 0.30928(3) 1.4206(3) 0.49763(12) 0.0502(4) Uani d . 1 1
H H3 0.2936 1.5494 0.4687 0.060 Uiso calc R 1 1
C C4 0.31021(3) 1.3469(3) 0.60828(11) 0.0451(3) Uani d . 1 1
C C5 0.33363(3) 1.1561(3) 0.64977(11) 0.0438(3) Uani d . 1 1
H H5 0.3345 1.1092 0.7239 0.053 Uiso calc R 1 1
C C6 0.35595(3) 1.0324(3) 0.58312(10) 0.0377(3) Uani d . 1 1
C C7 0.26320(4) 1.6273(4) 0.64047(16) 0.0725(5) Uani d . 1 1
H H7A 0.2715 1.8012 0.6091 0.109 Uiso calc R 1 1
H H7B 0.2498 1.6779 0.6989 0.109 Uiso calc R 1 1
H H7C 0.2506 1.5214 0.5851 0.109 Uiso calc R 1 1
C C8 0.37983(3) 0.8291(3) 0.63036(10) 0.0405(3) Uani d . 1 1
H H8 0.3803 0.7902 0.7051 0.049 Uiso calc R 1 1
C C9 0.42351(3) 0.5050(3) 0.62024(10) 0.0381(3) Uani d . 1 1
C C10 0.42235(3) 0.3824(3) 0.72409(11) 0.0460(3) Uani d . 1 1
H H10 0.4053 0.4280 0.7673 0.055 Uiso calc R 1 1
C C11 0.44638(3) 0.1933(3) 0.76319(11) 0.0463(3) Uani d . 1 1
H H11 0.4450 0.1111 0.8323 0.056 Uiso calc R 1 1
C C12 0.47241(3) 0.1226(3) 0.70280(11) 0.0411(3) Uani d . 1 1
C C13 0.47310(3) 0.2425(3) 0.59852(12) 0.0489(4) Uani d . 1 1
H H13 0.4902 0.1979 0.5556 0.059 Uiso calc R 1 1
C C14 0.44889(3) 0.4265(3) 0.55754(11) 0.0467(4) Uani d . 1 1
H H14 0.4496 0.4989 0.4867 0.056 Uiso calc R 1 1
C C15 0.5000 -0.0659(4) 0.7500 0.0474(5) Uani d S 1 2
H H15A 0.4922 -0.1658 0.8076 0.057 Uiso d 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 0.0016 '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'
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
C1 O1 H1 . 106.2
C4 O2 C7 . 117.30(12)
C8 N1 C9 . 121.08(11)
O1 C1 C2 . 119.22(12)
O1 C1 C6 . 121.38(12)
C2 C1 C6 . 119.40(12)
C1 C2 C3 . 121.01(13)
C1 C2 H2 . 119.5
C3 C2 H2 . 119.5
C2 C3 C4 . 120.06(13)
C2 C3 H3 . 120.0
C4 C3 H3 . 120.0
O2 C4 C5 . 115.87(12)
O2 C4 C3 . 124.94(13)
C5 C4 C3 . 119.19(12)
C4 C5 C6 . 121.39(12)
C4 C5 H5 . 119.3
C6 C5 H5 . 119.3
C5 C6 C1 . 118.95(12)
C5 C6 C8 . 119.31(11)
C1 C6 C8 . 121.75(11)
O2 C7 H7A . 109.5
O2 C7 H7B . 109.5
H7A C7 H7B . 109.5
O2 C7 H7C . 109.5
H7A C7 H7C . 109.5
H7B C7 H7C . 109.5
N1 C8 C6 . 122.03(12)
N1 C8 H8 . 119.0
C6 C8 H8 . 119.0
C14 C9 C10 . 118.04(12)
C14 C9 N1 . 116.95(11)
C10 C9 N1 . 125.00(11)
C11 C10 C9 . 120.28(12)
C11 C10 H10 . 119.9
C9 C10 H10 . 119.9
C12 C11 C10 . 122.00(13)
C12 C11 H11 . 119.0
C10 C11 H11 . 119.0
C11 C12 C13 . 117.28(12)
C11 C12 C15 . 121.54(11)
C13 C12 C15 . 121.11(11)
C14 C13 C12 . 121.29(12)
C14 C13 H13 . 119.4
C12 C13 H13 . 119.4
C13 C14 C9 . 121.04(13)
C13 C14 H14 . 119.5
C9 C14 H14 . 119.5
C12 C15 C12 2_656 110.27(15)
C12 C15 H15A 2_656 106.7
C12 C15 H15A . 106.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.3548(15)
O1 H1 . 0.8879
O2 C4 . 1.3754(16)
O2 C7 . 1.4168(19)
N1 C8 . 1.2802(16)
N1 C9 . 1.4176(16)
C1 C2 . 1.379(2)
C1 C6 . 1.4074(18)
C2 C3 . 1.3819(19)
C2 H2 . 0.9300
C3 C4 . 1.392(2)
C3 H3 . 0.9300
C4 C5 . 1.3787(19)
C5 C6 . 1.3901(18)
C5 H5 . 0.9300
C6 C8 . 1.4520(18)
C7 H7A . 0.9600
C7 H7B . 0.9600
C7 H7C . 0.9600
C8 H8 . 0.9300
C9 C14 . 1.3852(17)
C9 C10 . 1.3926(18)
C10 C11 . 1.3822(19)
C10 H10 . 0.9300
C11 C12 . 1.3814(18)
C11 H11 . 0.9300
C12 C13 . 1.3908(19)
C12 C15 . 1.5161(17)
C13 C14 . 1.3795(19)
C13 H13 . 0.9300
C14 H14 . 0.9300
C15 C12 2_656 1.5161(17)
C15 H15A . 0.9160
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 N1 0.89 1.81 2.6177(15) 150.5
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
C6 C8 N1 C9 179.75(11)
