#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/89/2238903.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_2238903
loop_
_publ_author_name
'Sajitha, N. R.'
'Sithambaresan, M.'
'Kurup, M. R. Prathapachandra'
_publ_section_title
;
 5,5'-Bis(benzyloxy)-2,2'-[hydrazinediylidenebis(methanylylidene)]diphenol
;
_journal_coeditor_code           NG5346
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1755
_journal_paper_doi               10.1107/S1600536813030171
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C28 H24 N2 O4'
_chemical_formula_moiety         'C28 H24 N2 O4'
_chemical_formula_sum            'C28 H24 N2 O4'
_chemical_formula_weight         452.49
_chemical_name_common
;
1,2-Bis(4-benzyloxy-2-hydroxybenzylidene)hydrazine
;
_chemical_name_systematic
;
5,5'-Bis(benzyloxy)-2,2'-[hydrazinediylidenebis(methanylylidene)]diphenol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.699(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.4748(17)
_cell_length_b                   5.3630(6)
_cell_length_c                   17.021(2)
_cell_measurement_reflns_used    1647
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.245
_cell_measurement_theta_min      3.266
_cell_volume                     1138.7(2)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2010)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6320
_diffrn_reflns_theta_full        28.17
_diffrn_reflns_theta_max         28.17
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9824
_exptl_absorpt_correction_T_min  0.9653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.150
_refine_ls_extinction_coef       0.0115(19)
_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   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2738
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0435
_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)+(0.0436P)²+0.1778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1220
_reflns_number_gt                1593
_reflns_number_total             2738
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ng5346.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2238903
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_symmetry_multiplicity
O O1 0.38498(9) 0.6629(2) 0.90134(6) 0.0614(4) Uani d . 1 1
O O2 0.36761(13) 0.8385(2) 0.62715(7) 0.0803(4) Uani d D 1 1
N N1 0.47835(11) 0.5470(3) 0.53460(7) 0.0601(4) Uani d . 1 1
C C1 0.23742(16) 0.7056(3) 1.04210(9) 0.0663(5) Uani d . 1 1
H H1 0.2071 0.5745 1.0138 0.080 Uiso calc R 1 1
C C2 0.22037(16) 0.7219(4) 1.12153(10) 0.0699(5) Uani d . 1 1
H H2 0.1786 0.6028 1.1464 0.084 Uiso calc R 1 1
C C3 0.26443(16) 0.9118(4) 1.16380(10) 0.0665(5) Uani d . 1 1
H H3 0.2522 0.9238 1.2175 0.080 Uiso calc R 1 1
C C4 0.32641(17) 1.0844(4) 1.12737(11) 0.0742(6) Uani d . 1 1
H H4 0.3573 1.2133 1.1563 0.089 Uiso calc R 1 1
C C5 0.34358(16) 1.0684(3) 1.04737(11) 0.0706(5) Uani d . 1 1
H H5 0.3862 1.1868 1.0228 0.085 Uiso calc R 1 1
C C6 0.29828(14) 0.8791(3) 1.00385(9) 0.0553(4) Uani d . 1 1
C C7 0.31240(16) 0.8630(3) 0.91687(9) 0.0675(5) Uani d . 1 1
H H7A 0.2439 0.8320 0.8911 0.081 Uiso calc R 1 1
H H7B 0.3410 1.0185 0.8970 0.081 Uiso calc R 1 1
C C8 0.40808(13) 0.6150(3) 0.82489(9) 0.0505(4) Uani d . 1 1
C C9 0.37165(14) 0.7540(3) 0.76205(9) 0.0565(4) Uani d . 1 1
H H9 0.3261 0.8887 0.7701 0.068 Uiso calc R 1 1
C C10 0.40315(14) 0.6925(3) 0.68662(9) 0.0539(4) Uani d . 1 1
C C11 0.46947(13) 0.4874(3) 0.67316(8) 0.0512(4) Uani d . 1 1
C C12 0.50273(14) 0.3498(3) 0.73856(10) 0.0611(5) Uani d . 1 1
H H12 0.5461 0.2110 0.7310 0.073 Uiso calc R 1 1
C C13 0.47411(14) 0.4112(3) 0.81321(9) 0.0594(5) Uani d . 1 1
H H13 0.4986 0.3173 0.8557 0.071 Uiso calc R 1 1
C C14 0.50412(14) 0.4193(3) 0.59605(9) 0.0581(4) Uani d . 1 1
H H14 0.5466 0.2782 0.5902 0.070 Uiso calc R 1 1
H H2' 0.3950(16) 0.782(4) 0.5836(10) 0.096(7) Uiso d 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 0.0000 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_3
_geom_angle
C8 O1 C7 . 117.41(12)
C10 O2 H2' . 107.8(14)
C14 N1 N1 3_666 113.47(19)
C6 C1 C2 . 121.17(17)
C6 C1 H1 . 119.4
C2 C1 H1 . 119.4
C3 C2 C1 . 120.14(18)
C3 C2 H2 . 119.9
C1 C2 H2 . 119.9
C2 C3 C4 . 119.79(17)
C2 C3 H3 . 120.1
C4 C3 H3 . 120.1
C3 C4 C5 . 120.15(18)
C3 C4 H4 . 119.9
C5 C4 H4 . 119.9
C6 C5 C4 . 120.57(18)
C6 C5 H5 . 119.7
C4 C5 H5 . 119.7
C1 C6 C5 . 118.16(16)
C1 C6 C7 . 120.25(16)
C5 C6 C7 . 121.58(16)
O1 C7 C6 . 107.98(13)
O1 C7 H7A . 110.1
C6 C7 H7A . 110.1
O1 C7 H7B . 110.1
C6 C7 H7B . 110.1
H7A C7 H7B . 108.4
O1 C8 C9 . 124.69(15)
O1 C8 C13 . 114.82(14)
C9 C8 C13 . 120.49(14)
C8 C9 C10 . 119.72(16)
C8 C9 H9 . 120.1
C10 C9 H9 . 120.1
O2 C10 C9 . 117.49(15)
O2 C10 C11 . 121.55(14)
C9 C10 C11 . 120.95(15)
C12 C11 C10 . 117.17(14)
C12 C11 C14 . 120.39(16)
C10 C11 C14 . 122.44(15)
C13 C12 C11 . 122.50(16)
C13 C12 H12 . 118.8
C11 C12 H12 . 118.8
C12 C13 C8 . 119.15(16)
C12 C13 H13 . 120.4
C8 C13 H13 . 120.4
N1 C14 C11 . 122.21(17)
N1 C14 H14 . 118.9
C11 C14 H14 . 118.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C8 . 1.3607(17)
O1 C7 . 1.431(2)
O2 C10 . 1.3505(19)
O2 H2' . 0.874(15)
N1 C14 . 1.288(2)
N1 N1 3_666 1.396(2)
C1 C6 . 1.370(2)
C1 C2 . 1.374(2)
C1 H1 . 0.9300
C2 C3 . 1.359(3)
C2 H2 . 0.9300
C3 C4 . 1.360(3)
C3 H3 . 0.9300
C4 C5 . 1.384(2)
C4 H4 . 0.9300
C5 C6 . 1.374(3)
C5 H5 . 0.9300
C6 C7 . 1.496(2)
C7 H7A . 0.9700
C7 H7B . 0.9700
C8 C9 . 1.376(2)
C8 C13 . 1.385(2)
C9 C10 . 1.387(2)
C9 H9 . 0.9300
C10 C11 . 1.397(2)
C11 C12 . 1.394(2)
C11 C14 . 1.434(2)
C12 C13 . 1.364(2)
C12 H12 . 0.9300
C13 H13 . 0.9300
C14 H14 . 0.9300
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
O2 H2' N1 0.87(2) 1.84(2) 2.625(2) 148(2)
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
C6 C1 C2 C3 . -0.3(3)
C1 C2 C3 C4 . -0.7(3)
C2 C3 C4 C5 . 0.7(3)
C3 C4 C5 C6 . 0.1(3)
C2 C1 C6 C5 . 1.1(3)
C2 C1 C6 C7 . -177.71(17)
C4 C5 C6 C1 . -1.0(3)
C4 C5 C6 C7 . 177.77(17)
C8 O1 C7 C6 . 179.40(14)
C1 C6 C7 O1 . -74.4(2)
C5 C6 C7 O1 . 106.85(19)
C7 O1 C8 C9 . 4.0(2)
C7 O1 C8 C13 . -176.67(16)
O1 C8 C9 C10 . 177.95(16)
C13 C8 C9 C10 . -1.4(3)
C8 C9 C10 O2 . -178.25(16)
C8 C9 C10 C11 . 1.5(3)
O2 C10 C11 C12 . 179.36(16)
C9 C10 C11 C12 . -0.4(2)
O2 C10 C11 C14 . 0.2(3)
C9 C10 C11 C14 . -179.61(16)
C10 C11 C12 C13 . -0.9(3)
C14 C11 C12 C13 . 178.29(17)
C11 C12 C13 C8 . 1.1(3)
O1 C8 C13 C12 . -179.31(16)
C9 C8 C13 C12 . 0.1(3)
N1 N1 C14 C11 3_666 178.83(17)
C12 C11 C14 N1 . -177.39(17)
C10 C11 C14 N1 . 1.8(3)
