#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/37/2203733.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_2203733
loop_
_publ_author_name
'S. M. Malathy Sony'
'P. Charles'
'M. N. Ponnuswamy'
'H. S. Yathirajan'
_publ_section_title
;2,2'-{(Z)-Ethane-1,2-diylbis[(Z)-o-phenylenenitrilomethylidyne]}diphenol
 (EIEP)
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1078
_journal_page_last               o1080
_journal_paper_doi               10.1107/S1600536804012073
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C28 H24 N2 O2'
_chemical_formula_moiety         'C28 H24 N2 O2'
_chemical_formula_sum            'C28 H24 N2 O2'
_chemical_formula_weight         420.49
_chemical_name_systematic
;
2,2'-{(Z)-Ethane-1,2-diylbis[(Z)-o-phenylenenitrilomethylidyne]}diphenol
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.15(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.817(3)
_cell_length_b                   13.762(6)
_cell_length_c                   6.873(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      8
_cell_volume                     1096.6(6)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
'PLATON (Spek, 1990) and ORTEP-3 (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       'non-profiled ω/2θ'
_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  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0639
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3425
_diffrn_reflns_theta_full        29.95
_diffrn_reflns_theta_max         29.95
_diffrn_reflns_theta_min         1.76
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.171
_refine_ls_extinction_coef       0.039(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         3179
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1545
_refine_ls_R_factor_gt           0.0572
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0961P)²+0.0403P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1504
_refine_ls_wR_factor_ref         0.1991
_reflns_number_gt                1504
_reflns_number_total             3179
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6383.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2203733
_cod_database_fobs_code          2203733
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_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_type_symbol
C1 0.95547(17) 0.12126(14) 0.3165(3) 0.0384(5) Uani d . 1 C
C2 1.03434(17) 0.05488(14) 0.2642(3) 0.0392(5) Uani d . 1 C
C3 1.14800(19) 0.06032(17) 0.3620(3) 0.0477(5) Uani d . 1 C
H3 1.2014 0.0171 0.3280 0.057 Uiso calc R 1 H
C4 1.1842(2) 0.1278(2) 0.5082(3) 0.0552(6) Uani d . 1 C
H4 1.2609 0.1291 0.5732 0.066 Uiso calc R 1 H
C5 1.1068(2) 0.19376(18) 0.5584(3) 0.0536(6) Uani d . 1 C
H5 1.1313 0.2402 0.6558 0.064 Uiso calc R 1 H
C6 0.99255(19) 0.19053(17) 0.4633(3) 0.0473(5) Uani d . 1 C
H6 0.9401 0.2347 0.4973 0.057 Uiso calc R 1 H
C7 0.99653(18) -0.01933(15) 0.1034(3) 0.0429(5) Uani d . 1 C
H7A 0.9177 -0.0386 0.1048 0.051 Uiso calc R 1 H
H7B 1.0449 -0.0766 0.1309 0.051 Uiso calc R 1 H
N8 0.84017(14) 0.11922(12) 0.2103(3) 0.0425(4) Uani d . 1 N
C9 0.75664(19) 0.13183(16) 0.3012(3) 0.0475(5) Uani d . 1 C
H9 0.7732 0.1416 0.4376 0.057 Uiso calc R 1 H
C10 0.63706(18) 0.13139(16) 0.1995(3) 0.0481(5) Uani d . 1 C
C11 0.60639(19) 0.12047(17) -0.0074(4) 0.0523(6) Uani d . 1 C
C12 0.4916(2) 0.1182(2) -0.0978(4) 0.0694(8) Uani d . 1 C
H12 0.4712 0.1104 -0.2345 0.083 Uiso calc R 1 H
C13 0.4078(2) 0.1272(2) 0.0120(5) 0.0766(8) Uani d . 1 C
H13 0.3307 0.1251 -0.0509 0.092 Uiso calc R 1 H
C14 0.4352(2) 0.1392(2) 0.2140(5) 0.0805(9) Uani d . 1 C
H14 0.3772 0.1462 0.2870 0.097 Uiso calc R 1 H
C15 0.5490(2) 0.1408(2) 0.3073(4) 0.0697(8) Uani d . 1 C
H15 0.5677 0.1483 0.4442 0.084 Uiso calc R 1 H
O16 0.68777(14) 0.11178(16) -0.1208(2) 0.0698(6) Uani d . 1 O
H16 0.7513 0.1049 -0.0490 0.105 Uiso calc R 1 H
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_site_symmetry_3
_geom_angle
C6 C1 C2 . . 119.98(19)
C6 C1 N8 . . 121.50(18)
C2 C1 N8 . . 118.43(18)
C3 C2 C1 . . 118.13(19)
C3 C2 C7 . . 121.03(18)
C1 C2 C7 . . 120.83(18)
C4 C3 C2 . . 121.9(2)
C4 C3 H3 . . 119.1
C2 C3 H3 . . 119.1
C3 C4 C5 . . 120.0(2)
C3 C4 H4 . . 120.0
C5 C4 H4 . . 120.0
C4 C5 C6 . . 119.7(2)
C4 C5 H5 . . 120.2
C6 C5 H5 . . 120.2
C5 C6 C1 . . 120.3(2)
C5 C6 H6 . . 119.8
C1 C6 H6 . . 119.8
C2 C7 C7 . 3_755 112.5(2)
C2 C7 H7A . . 109.1
C7 C7 H7A 3_755 . 109.1
C2 C7 H7B . . 109.1
C7 C7 H7B 3_755 . 109.1
H7A C7 H7B . . 107.8
C9 N8 C1 . . 120.15(18)
N8 C9 C10 . . 122.4(2)
N8 C9 H9 . . 118.8
C10 C9 H9 . . 118.8
C15 C10 C11 . . 118.3(2)
C15 C10 C9 . . 120.0(2)
C11 C10 C9 . . 121.6(2)
O16 C11 C12 . . 119.0(2)
O16 C11 C10 . . 121.2(2)
C12 C11 C10 . . 119.8(2)
C13 C12 C11 . . 120.4(3)
C13 C12 H12 . . 119.8
C11 C12 H12 . . 119.8
C12 C13 C14 . . 121.1(3)
C12 C13 H13 . . 119.4
C14 C13 H13 . . 119.4
C13 C14 C15 . . 119.5(3)
C13 C14 H14 . . 120.3
C15 C14 H14 . . 120.3
C14 C15 C10 . . 120.9(3)
C14 C15 H15 . . 119.5
C10 C15 H15 . . 119.5
C11 O16 H16 . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C6 . 1.396(3)
C1 C2 . 1.401(3)
C1 N8 . 1.416(3)
C2 C3 . 1.383(3)
C2 C7 . 1.508(3)
C3 C4 . 1.375(3)
C3 H3 . 0.93
C4 C5 . 1.379(3)
C4 H4 . 0.93
C5 C6 . 1.382(3)
C5 H5 . 0.93
C6 H6 . 0.93
C7 C7 3_755 1.534(4)
C7 H7A . 0.97
C7 H7B . 0.97
N8 C9 . 1.278(3)
C9 C10 . 1.450(3)
C9 H9 . 0.93
C10 C15 . 1.395(3)
C10 C11 . 1.405(3)
C11 O16 . 1.355(3)
C11 C12 . 1.379(3)
C12 C13 . 1.361(4)
C12 H12 . 0.93
C13 C14 . 1.373(4)
C13 H13 . 0.93
C14 C15 . 1.374(3)
C14 H14 . 0.93
C15 H15 . 0.93
O16 H16 . 0.82
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_4
_geom_torsion
C6 C1 C2 C3 . 0.2(3)
N8 C1 C2 C3 . 176.95(18)
C6 C1 C2 C7 . -178.86(18)
N8 C1 C2 C7 . -2.1(3)
C1 C2 C3 C4 . 0.5(3)
C7 C2 C3 C4 . 179.62(19)
C2 C3 C4 C5 . -1.2(3)
C3 C4 C5 C6 . 1.0(3)
C4 C5 C6 C1 . -0.3(3)
C2 C1 C6 C5 . -0.4(3)
N8 C1 C6 C5 . -176.99(19)
C3 C2 C7 C7 3_755 -91.0(3)
C1 C2 C7 C7 3_755 88.1(3)
C6 C1 N8 C9 . -42.4(3)
C2 C1 N8 C9 . 140.9(2)
C1 N8 C9 C10 . 179.39(18)
N8 C9 C10 C15 . 176.9(2)
N8 C9 C10 C11 . -2.3(4)
C15 C10 C11 O16 . 179.4(2)
C9 C10 C11 O16 . -1.3(3)
C15 C10 C11 C12 . -0.8(3)
C9 C10 C11 C12 . 178.5(2)
O16 C11 C12 C13 . -179.7(3)
C10 C11 C12 C13 . 0.5(4)
C11 C12 C13 C14 . 0.4(5)
C12 C13 C14 C15 . -0.9(5)
C13 C14 C15 C10 . 0.7(5)
C11 C10 C15 C14 . 0.2(4)
C9 C10 C15 C14 . -179.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 136728893
