#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/61/2206131.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_2206131
loop_
_publ_author_name
'Kos̨ar, Bas̨ak'
'Albayrak, Çiğdem'
'Odabaşoğlu, Mustafa'
'Büyükgüngör, Orhan'
_publ_section_title
;
 (E)-4-Methoxy-2-[(4-nitrophenyl)iminomethyl]phenol
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2106
_journal_page_last               o2108
_journal_paper_doi               10.1107/S1600536805018155
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C14 H12 N2 O4'
_chemical_formula_moiety         'C14 H12 N2 O4'
_chemical_formula_sum            'C14 H12 N2 O4'
_chemical_formula_weight         272.26
_chemical_name_systematic
;
(E)-4-Methoxy-2-[(4-nitrophenyl)iminomethyl]phenol
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 101.755(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9769(9)
_cell_length_b                   14.3789(13)
_cell_length_c                   10.0589(10)
_cell_measurement_reflns_used    9989
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.83
_cell_measurement_theta_min      1.42
_cell_volume                     1271.2(2)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (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 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Stoe IPDS-II'
_diffrn_measurement_method       'rotation method'
_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  0.0722
_diffrn_reflns_av_sigmaI/netI    0.0578
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19135
_diffrn_reflns_theta_full        28.09
_diffrn_reflns_theta_max         28.09
_diffrn_reflns_theta_min         2.51
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9888
_exptl_absorpt_correction_T_min  0.9767
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED; Stoe & Cie, 2002)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.106
_refine_diff_density_min         -0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.817
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.817
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.05P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.1044
_reflns_number_gt                1230
_reflns_number_total             3049
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6675.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2206131
_cod_database_fobs_code          2206131
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_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 0.08289(19) 0.47916(11) 0.36339(18) 0.0524(5) Uani d . 1 C
N2 0.18738(15) 0.55222(9) 0.40484(15) 0.0557(4) Uani d . 1 N
O3 0.45960(14) 0.60752(9) 0.52155(15) 0.0799(5) Uani d . 1 O
H33 0.3921 0.5699 0.4928 0.120 Uiso calc R 1 H
C7 0.1500(2) 0.63745(12) 0.38352(18) 0.0561(5) Uani d . 1 C
H7 0.0511 0.6518 0.3399 0.067 Uiso calc R 1 H
C12 0.5036(2) 0.76916(13) 0.5333(2) 0.0649(5) Uani d . 1 C
H12 0.6032 0.7582 0.5783 0.078 Uiso calc R 1 H
C13 0.4064(2) 0.69466(12) 0.49318(19) 0.0587(5) Uani d . 1 C
C4 -0.09738(19) 0.32643(12) 0.28793(19) 0.0567(5) Uani d . 1 C
C2 0.1359(2) 0.39074(11) 0.4000(2) 0.0603(5) Uani d . 1 C
H2 0.2339 0.3830 0.4509 0.072 Uiso calc R 1 H
C6 -0.0646(2) 0.48993(13) 0.2897(2) 0.0629(5) Uani d . 1 C
H6 -0.1023 0.5492 0.2661 0.075 Uiso calc R 1 H
C8 0.25691(19) 0.71214(11) 0.42517(18) 0.0549(5) Uani d . 1 C
C5 -0.1552(2) 0.41352(12) 0.2515(2) 0.0647(5) Uani d . 1 C
H5 -0.2539 0.4206 0.2018 0.078 Uiso calc R 1 H
O4 0.26926(16) 0.96910(8) 0.42188(15) 0.0771(4) Uani d . 1 O
C9 0.2084(2) 0.80430(11) 0.39989(19) 0.0593(5) Uani d . 1 C
H9 0.1092 0.8164 0.3547 0.071 Uiso calc R 1 H
N1 -0.1926(2) 0.24483(12) 0.24440(19) 0.0727(5) Uani d . 1 N
C11 0.4543(2) 0.85820(13) 0.5074(2) 0.0644(5) Uani d . 1 C
H11 0.5211 0.9073 0.5346 0.077 Uiso calc R 1 H
C3 0.0461(2) 0.31393(12) 0.3623(2) 0.0638(5) Uani d . 1 C
H3 0.0824 0.2545 0.3871 0.077 Uiso calc R 1 H
O2 -0.1413(2) 0.16804(11) 0.27642(19) 0.1014(6) Uani d . 1 O
C10 0.3065(2) 0.87682(12) 0.4414(2) 0.0599(5) Uani d . 1 C
O1 -0.31999(18) 0.25807(11) 0.17620(18) 0.1002(6) Uani d . 1 O
C14 0.1203(2) 0.99100(14) 0.3516(3) 0.0868(7) Uani d . 1 C
H14A 0.1090 1.0573 0.3445 0.130 Uiso calc R 1 H
H14B 0.0477 0.9663 0.4004 0.130 Uiso calc R 1 H
H14C 0.1031 0.9643 0.2624 0.130 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
C2 C1 C6 118.99(16) ?
C2 C1 N2 115.69(15) ?
C6 C1 N2 125.32(16) ?
C7 N2 C1 121.86(15) ?
C13 O3 H33 109.5 ?
N2 C7 C8 121.92(16) ?
N2 C7 H7 119.0 ?
C8 C7 H7 119.0 ?
C11 C12 C13 120.61(17) ?
C11 C12 H12 119.7 ?
C13 C12 H12 119.7 ?
O3 C13 C12 118.68(16) ?
O3 C13 C8 122.19(16) ?
C12 C13 C8 119.12(17) ?
C3 C4 C5 121.93(17) ?
C3 C4 N1 119.13(17) ?
C5 C4 N1 118.93(16) ?
C3 C2 C1 120.99(16) ?
C3 C2 H2 119.5 ?
C1 C2 H2 119.5 ?
C5 C6 C1 120.40(17) ?
C5 C6 H6 119.8 ?
C1 C6 H6 119.8 ?
C13 C8 C9 119.34(16) ?
C13 C8 C7 121.50(16) ?
C9 C8 C7 119.15(15) ?
C6 C5 C4 118.90(17) ?
C6 C5 H5 120.6 ?
C4 C5 H5 120.6 ?
C10 O4 C14 117.67(15) ?
C10 C9 C8 120.43(16) ?
C10 C9 H9 119.8 ?
C8 C9 H9 119.8 ?
O2 N1 O1 123.43(18) yes
O2 N1 C4 118.85(18) ?
O1 N1 C4 117.72(18) ?
C12 C11 C10 121.06(17) ?
C12 C11 H11 119.5 ?
C10 C11 H11 119.5 ?
C4 C3 C2 118.76(17) ?
C4 C3 H3 120.6 ?
C2 C3 H3 120.6 ?
O4 C10 C9 124.62(17) ?
O4 C10 C11 115.94(15) ?
C9 C10 C11 119.44(16) ?
O4 C14 H14A 109.5 ?
O4 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
O4 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.381(2) ?
C1 C6 1.388(2) ?
C1 N2 1.413(2) ?
N2 C7 1.277(2) yes
O3 C13 1.351(2) yes
O3 H33 0.8200 ?
C7 C8 1.444(2) ?
C7 H7 0.9300 ?
C12 C11 1.362(2) ?
C12 C13 1.389(2) ?
C12 H12 0.9300 ?
C13 C8 1.399(2) ?
C4 C3 1.363(2) ?
C4 C5 1.376(2) ?
C4 N1 1.465(2) yes
C2 C3 1.375(2) ?
C2 H2 0.9300 ?
C6 C5 1.374(2) ?
C6 H6 0.9300 ?
C8 C9 1.402(2) ?
C5 H5 0.9300 ?
O4 C10 1.373(2) ?
O4 C14 1.415(2) ?
C9 C10 1.374(2) ?
C9 H9 0.9300 ?
N1 O2 1.214(2) yes
N1 O1 1.223(2) yes
C11 C10 1.384(2) ?
C11 H11 0.9300 ?
C3 H3 0.9300 ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
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 1.89 2.6102(19) 146
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
C2 C1 N2 C7 -176.33(18)
C6 C1 N2 C7 4.2(3)
C1 N2 C7 C8 -179.66(17)
C11 C12 C13 O3 -179.64(19)
C11 C12 C13 C8 0.2(3)
C6 C1 C2 C3 1.3(3)
N2 C1 C2 C3 -178.27(18)
C2 C1 C6 C5 -1.3(3)
N2 C1 C6 C5 178.15(19)
O3 C13 C8 C9 179.45(18)
C12 C13 C8 C9 -0.4(3)
O3 C13 C8 C7 1.1(3)
C12 C13 C8 C7 -178.72(17)
N2 C7 C8 C13 -1.1(3)
N2 C7 C8 C9 -179.43(19)
C1 C6 C5 C4 0.3(3)
C3 C4 C5 C6 0.9(3)
N1 C4 C5 C6 -178.54(18)
C13 C8 C9 C10 0.0(3)
C7 C8 C9 C10 178.35(18)
C3 C4 N1 O2 0.4(3)
C5 C4 N1 O2 179.9(2)
C3 C4 N1 O1 -179.0(2)
C5 C4 N1 O1 0.5(3)
C13 C12 C11 C10 0.4(3)
C5 C4 C3 C2 -1.0(3)
N1 C4 C3 C2 178.47(18)
C1 C2 C3 C4 -0.1(3)
C14 O4 C10 C9 -1.3(3)
C14 O4 C10 C11 178.41(19)
C8 C9 C10 O4 -179.67(19)
C8 C9 C10 C11 0.6(3)
C12 C11 C10 O4 179.45(19)
C12 C11 C10 C9 -0.8(3)
