#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/49/2234904.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_2234904
loop_
_publ_author_name
'Ourari, Ali'
'Baameur, Lotfi'
'Bouacida, Sofiane'
'Ouari, Kamel'
_publ_section_title
;
 2-[({2-[(2-Hydroxy-5-methoxybenzylidene)amino]ethyl}imino)methyl]-4-methoxyphenol
;
_journal_coeditor_code           BQ2353
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1760
_journal_paper_doi               10.1107/S1600536812018405
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C18 H20 N2 O4'
_chemical_formula_moiety         'C18 H20 N2 O4'
_chemical_formula_sum            'C18 H20 N2 O4'
_chemical_formula_weight         328.36
_chemical_name_systematic
;
2-[({2-[(2-Hydroxy-5-methoxybenzylidene)amino]ethyl}imino)methyl]-
4-methoxyphenol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 92.001(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.0040(12)
_cell_length_b                   5.9722(3)
_cell_length_c                   9.3128(8)
_cell_measurement_reflns_used    1761
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.373
_cell_measurement_theta_min      0.998
_cell_volume                     833.98(11)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor 1997)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2002 (Burla et al., 2005)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_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  0.0208
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3001
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.72
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.164
_refine_ls_extinction_coef       0.08(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0541
_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)+(0.1010P)²+0.0006P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1438
_refine_ls_wR_factor_ref         0.1666
_reflns_number_gt                1097
_reflns_number_total             1664
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bq2353.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2234904
_cod_database_fobs_code          2234904
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C C1 0.00544(12) 0.5332(3) 0.42227(18) 0.0554(5) Uani d . 1 1
H H1A 0.0237 0.404 0.3674 0.066 Uiso calc R 1 1
H H1B -0.0511 0.586 0.3816 0.066 Uiso calc R 1 1
C C3 0.13689(11) 0.6835(3) 0.32973(18) 0.0500(5) Uani d . 1 1
H H3 0.1399 0.5537 0.2749 0.06 Uiso calc R 1 1
C C4 0.20642(11) 0.8520(3) 0.31789(17) 0.0488(5) Uani d . 1 1
C C5 0.20521(13) 1.0483(3) 0.40154(19) 0.0545(5) Uani d . 1 1
C C6 0.27360(14) 1.2037(3) 0.3894(2) 0.0620(5) Uani d . 1 1
H H6 0.2731 1.3341 0.4439 0.074 Uiso calc R 1 1
C C7 0.34154(14) 1.1672(3) 0.2983(2) 0.0623(5) Uani d . 1 1
H H7 0.3863 1.2739 0.2909 0.075 Uiso calc R 1 1
C C8 0.34469(12) 0.9719(3) 0.21605(18) 0.0542(5) Uani d . 1 1
C C9 0.27715(11) 0.8166(3) 0.22553(18) 0.0515(5) Uani d . 1 1
H H9 0.2784 0.687 0.1702 0.062 Uiso calc R 1 1
C C10 0.42592(14) 0.7497(3) 0.0532(3) 0.0764(7) Uani d . 1 1
H H10A 0.4313 0.6263 0.119 0.115 Uiso calc R 1 1
H H10B 0.4781 0.7572 -0.0033 0.115 Uiso calc R 1 1
H H10C 0.3742 0.7287 -0.0089 0.115 Uiso calc R 1 1
N N2 0.07208(9) 0.7091(2) 0.41315(16) 0.0544(5) Uani d . 1 1
O O5 0.13958(10) 1.0889(2) 0.49361(15) 0.0712(5) Uani d . 1 1
H H5 0.1037 0.9853 0.4903 0.107 Uiso calc R 1 1
O O8 0.41724(10) 0.9514(2) 0.13122(15) 0.0727(5) Uani d . 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 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
N2 C1 C1 . 3_566 109.99(18)
N2 C1 H1A . . 109.7
C1 C1 H1A 3_566 . 109.7
N2 C1 H1B . . 109.7
C1 C1 H1B 3_566 . 109.7
H1A C1 H1B . . 108.2
N2 C3 C4 . . 121.80(15)
N2 C3 H3 . . 119.1
C4 C3 H3 . . 119.1
C9 C4 C5 . . 119.26(16)
C9 C4 C3 . . 120.03(15)
C5 C4 C3 . . 120.68(16)
O5 C5 C6 . . 119.26(16)
O5 C5 C4 . . 121.64(16)
C6 C5 C4 . . 119.10(17)
C7 C6 C5 . . 120.86(16)
C7 C6 H6 . . 119.6
C5 C6 H6 . . 119.6
C6 C7 C8 . . 120.91(16)
C6 C7 H7 . . 119.5
C8 C7 H7 . . 119.5
O8 C8 C9 . . 125.19(16)
O8 C8 C7 . . 115.64(15)
C9 C8 C7 . . 119.18(17)
C8 C9 C4 . . 120.69(16)
C8 C9 H9 . . 119.7
C4 C9 H9 . . 119.7
O8 C10 H10A . . 109.5
O8 C10 H10B . . 109.5
H10A C10 H10B . . 109.5
O8 C10 H10C . . 109.5
H10A C10 H10C . . 109.5
H10B C10 H10C . . 109.5
C3 N2 C1 . . 119.31(15)
C5 O5 H5 . . 109.5
C8 O8 C10 . . 117.41(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N2 . 1.455(2)
C1 C1 3_566 1.515(3)
C1 H1A . 0.97
C1 H1B . 0.97
C3 N2 . 1.275(2)
C3 C4 . 1.456(2)
C3 H3 . 0.93
C4 C9 . 1.405(2)
C4 C5 . 1.408(2)
C5 O5 . 1.350(2)
C5 C6 . 1.391(3)
C6 C7 . 1.366(3)
C6 H6 . 0.93
C7 C8 . 1.397(2)
C7 H7 . 0.93
C8 O8 . 1.373(2)
C8 C9 . 1.379(2)
C9 H9 . 0.93
C10 O8 . 1.415(2)
C10 H10A . 0.96
C10 H10B . 0.96
C10 H10C . 0.96
O5 H5 . 0.82
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
_geom_hbond_publ_flag
O5 H5 N2 . 0.8200 1.8500 2.5844(18) 148 yes
C10 H10C Cg 4_564 0.96 2.64 3.521(2) 152 yes
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
N2 C3 C4 C9 . 179.47(16)
N2 C3 C4 C5 . 1.4(3)
C9 C4 C5 O5 . -178.94(15)
C3 C4 C5 O5 . -0.9(3)
C9 C4 C5 C6 . 0.8(2)
C3 C4 C5 C6 . 178.82(15)
O5 C5 C6 C7 . 179.38(17)
C4 C5 C6 C7 . -0.3(3)
C5 C6 C7 C8 . -0.7(3)
C6 C7 C8 O8 . -178.45(17)
C6 C7 C8 C9 . 1.2(3)
O8 C8 C9 C4 . 178.87(17)
C7 C8 C9 C4 . -0.8(3)
C5 C4 C9 C8 . -0.2(2)
C3 C4 C9 C8 . -178.27(15)
C4 C3 N2 C1 . -178.95(15)
C1 C1 N2 C3 3_566 127.0(2)
C9 C8 O8 C10 . -3.6(3)
C7 C8 O8 C10 . 176.06(17)
