#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/61/2206132.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_2206132
loop_
_publ_author_name
'Koşar, Başak'
'Albayrak, Çiğdem'
'Odabaşoğlu, Mustafa'
'Büyükgüngör, Orhan'
_publ_section_title
;
 (E)-2-Ethoxy-6-[(4-nitrophenyl)iminomethyl]phenol
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2109
_journal_page_last               o2111
_journal_paper_doi               10.1107/S1600536805018167
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C15 H14 N2 O4'
_chemical_formula_moiety         'C15 H14 N2 O4'
_chemical_formula_sum            'C15 H14 N2 O4'
_chemical_formula_weight         286.28
_chemical_name_systematic
;
(E)-2-Ethoxy-6-[(4-nitrophenyl)iminomethyl]phenol
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 111.524(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   27.883(2)
_cell_length_b                   7.1237(7)
_cell_length_c                   14.7975(10)
_cell_measurement_reflns_used    11318
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.06
_cell_measurement_theta_min      1.48
_cell_volume                     2734.3(4)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       rotation
_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  0.0710
_diffrn_reflns_av_sigmaI/netI    0.0616
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16558
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         1.57
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_correction_T_min  0.9656
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'X-RED32 (Stoe & Cie, 2002)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.297
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.083
_refine_diff_density_min         -0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.809
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2693
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      0.805
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0349
_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)+(0.075P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0625
_refine_ls_wR_factor_ref         0.0685
_reflns_number_gt                1289
_reflns_number_total             2693
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6676.cif
_cod_data_source_block           I
_cod_original_cell_volume        2734.2(4)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2206132
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_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
N2 0.19145(5) 0.01499(17) 0.46671(9) 0.0541(3) Uani d U 1 N
O4 0.08969(4) 0.23344(16) 0.66700(8) 0.0698(3) Uani d . 1 O
C4 0.30980(6) -0.1273(2) 0.37268(13) 0.0582(4) Uani d U 1 C
C1 0.23027(6) -0.0365(2) 0.43092(11) 0.0514(4) Uani d U 1 C
C13 0.11459(6) 0.1315(2) 0.54012(12) 0.0524(4) Uani d . 1 C
O3 0.16196(4) 0.10675(15) 0.60865(7) 0.0647(3) Uani d . 1 O
H33 0.1818 0.0709 0.5829 0.097 Uiso calc R 1 H
C7 0.14488(6) 0.0428(2) 0.40868(12) 0.0552(4) Uani d . 1 C
H7 0.1369 0.0269 0.3424 0.066 Uiso calc R 1 H
C8 0.10437(6) 0.0979(2) 0.44210(11) 0.0502(4) Uani d . 1 C
C12 0.07507(6) 0.1970(2) 0.56943(12) 0.0560(4) Uani d . 1 C
C11 0.02645(6) 0.2202(2) 0.50197(13) 0.0638(5) Uani d . 1 C
H11 0.0002 0.2614 0.5216 0.077 Uiso calc R 1 H
N1 0.35282(7) -0.1742(2) 0.34188(15) 0.0774(5) Uani d U 1 N
O1 0.34245(6) -0.2107(2) 0.25592(12) 0.1027(5) Uani d U 1 O
C6 0.22042(6) -0.1233(2) 0.34157(11) 0.0617(4) Uani d . 1 C
H2 0.1867 -0.1510 0.3015 0.074 Uiso calc R 1 H
O2 0.39643(5) -0.1736(2) 0.40282(12) 0.1021(5) Uani d . 1 O
C2 0.28053(6) 0.0002(2) 0.49074(12) 0.0576(4) Uani d . 1 C
H6 0.2872 0.0559 0.5510 0.069 Uiso calc R 1 H
C5 0.26057(7) -0.1681(2) 0.31272(12) 0.0646(5) Uani d U 1 C
H3 0.2543 -0.2256 0.2530 0.078 Uiso calc R 1 H
C9 0.05420(6) 0.1236(2) 0.37502(12) 0.0613(4) Uani d . 1 C
H13 0.0469 0.0999 0.3095 0.074 Uiso calc R 1 H
C3 0.32096(6) -0.0450(2) 0.46198(13) 0.0618(5) Uani d U 1 C
H5 0.3549 -0.0203 0.5021 0.074 Uiso calc R 1 H
C10 0.01584(6) 0.1830(2) 0.40447(13) 0.0670(5) Uani d . 1 C
H12 -0.0174 0.1986 0.3593 0.080 Uiso calc R 1 H
C15 0.07949(7) 0.3888(2) 0.80025(12) 0.0752(5) Uani d . 1 C
H15A 0.0555 0.4539 0.8220 0.113 Uiso calc R 1 H
H15B 0.1077 0.4707 0.8051 0.113 Uiso calc R 1 H
H15C 0.0924 0.2800 0.8401 0.113 Uiso calc R 1 H
C14 0.05272(7) 0.3293(2) 0.69640(12) 0.0685(5) Uani d . 1 C
H14A 0.0241 0.2467 0.6906 0.082 Uiso calc R 1 H
H14B 0.0394 0.4383 0.6555 0.082 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
_geom_angle_publ_flag
C7 N2 C1 120.97(14) ?
C12 O4 C14 116.15(13) ?
C5 C4 C3 122.38(16) ?
C5 C4 N1 119.38(17) ?
C3 C4 N1 118.23(17) ?
C2 C1 C6 119.57(15) ?
C2 C1 N2 116.50(14) ?
C6 C1 N2 123.93(15) ?
O3 C13 C8 121.99(14) ?
O3 C13 C12 118.31(14) ?
C8 C13 C12 119.69(14) ?
C13 O3 H33 109.5 ?
N2 C7 C8 122.68(15) ?
N2 C7 H7 118.7 ?
C8 C7 H7 118.7 ?
C13 C8 C9 119.04(15) ?
C13 C8 C7 121.12(14) ?
C9 C8 C7 119.80(15) ?
C11 C12 O4 125.26(15) ?
C11 C12 C13 119.67(15) ?
O4 C12 C13 115.07(14) ?
C12 C11 C10 120.81(16) ?
C12 C11 H11 119.6 ?
C10 C11 H11 119.6 ?
O2 N1 O1 124.06(18) yes
O2 N1 C4 118.41(18) ?
O1 N1 C4 117.52(18) ?
C5 C6 C1 119.90(16) ?
C5 C6 H2 120.0 ?
C1 C6 H2 120.0 ?
C1 C2 C3 120.62(16) ?
C1 C2 H6 119.7 ?
C3 C2 H6 119.7 ?
C4 C5 C6 119.24(16) ?
C4 C5 H3 120.4 ?
C6 C5 H3 120.4 ?
C10 C9 C8 120.80(16) ?
C10 C9 H13 119.6 ?
C8 C9 H13 119.6 ?
C4 C3 C2 118.27(16) ?
C4 C3 H5 120.9 ?
C2 C3 H5 120.9 ?
C9 C10 C11 119.95(16) ?
C9 C10 H12 120.0 ?
C11 C10 H12 120.0 ?
C14 C15 H15A 109.5 ?
C14 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C14 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
O4 C14 C15 107.62(14) ?
O4 C14 H14A 110.2 ?
C15 C14 H14A 110.2 ?
O4 C14 H14B 110.2 ?
C15 C14 H14B 110.2 ?
H14A C14 H14B 108.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N2 C7 1.2825(17) yes
N2 C1 1.4168(18) ?
O4 C12 1.3734(18) ?
O4 C14 1.4310(17) ?
C4 C5 1.365(2) ?
C4 C3 1.373(2) ?
C4 N1 1.469(2) yes
C1 C2 1.380(2) ?
C1 C6 1.393(2) ?
C13 O3 1.3496(16) yes
C13 C8 1.393(2) ?
C13 C12 1.404(2) ?
O3 H33 0.8200 ?
C7 C8 1.443(2) ?
C7 H7 0.9300 ?
C8 C9 1.399(2) ?
C12 C11 1.367(2) ?
C11 C10 1.388(2) ?
C11 H11 0.9300 ?
N1 O2 1.2197(18) yes
N1 O1 1.2246(18) yes
C6 C5 1.374(2) ?
C6 H2 0.9300 ?
C2 C3 1.381(2) ?
C2 H6 0.9300 ?
C5 H3 0.9300 ?
C9 C10 1.362(2) ?
C9 H13 0.9300 ?
C3 H5 0.9300 ?
C10 H12 0.9300 ?
C15 C14 1.502(2) ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
C14 H14A 0.9700 ?
C14 H14B 0.9700 ?
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
O3 H33 N2 0.82 1.88 2.6043(16) 147
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
C7 N2 C1 C2 157.85(14)
C7 N2 C1 C6 -23.4(2)
C1 N2 C7 C8 -179.14(13)
O3 C13 C8 C9 179.02(13)
C12 C13 C8 C9 -2.3(2)
O3 C13 C8 C7 -2.9(2)
C12 C13 C8 C7 175.74(13)
N2 C7 C8 C13 2.8(2)
N2 C7 C8 C9 -179.18(14)
C14 O4 C12 C11 -9.9(2)
C14 O4 C12 C13 169.91(14)
O3 C13 C12 C11 -178.77(14)
C8 C13 C12 C11 2.5(2)
O3 C13 C12 O4 1.4(2)
C8 C13 C12 O4 -177.31(14)
O4 C12 C11 C10 178.64(15)
C13 C12 C11 C10 -1.2(2)
C5 C4 N1 O2 -164.98(16)
C3 C4 N1 O2 14.4(2)
C5 C4 N1 O1 15.4(2)
C3 C4 N1 O1 -165.29(16)
C2 C1 C6 C5 -1.4(2)
N2 C1 C6 C5 179.93(14)
C6 C1 C2 C3 1.3(2)
N2 C1 C2 C3 -179.95(14)
C3 C4 C5 C6 0.9(2)
N1 C4 C5 C6 -179.73(14)
C1 C6 C5 C4 0.3(2)
C13 C8 C9 C10 0.8(2)
C7 C8 C9 C10 -177.29(15)
C5 C4 C3 C2 -1.1(2)
N1 C4 C3 C2 179.61(13)
C1 C2 C3 C4 -0.1(2)
C8 C9 C10 C11 0.5(2)
C12 C11 C10 C9 -0.4(3)
C12 O4 C14 C15 -168.97(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21180606
