#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2006466.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_2006466
loop_
_publ_author_name
'Vijayalakshmi, L.'
'Parthasarathi, V.'
'Manishanker, P.'
_publ_section_title
;
 <i>N</i>-(<i>p</i>-Hydroxybenzylidene)phenylamine <i>N</i>-Oxide
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1343
_journal_page_last               1344
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C13 H11 N1 O2'
_chemical_formula_structural     'C13 H11 N1 O2'
_chemical_formula_sum            'C13 H11 N O2'
_chemical_formula_weight         213.23
_chemical_melting_point          487
_chemical_name_common            '\a-(4--Hydroxy phenyl)-N-Phenyl nitrone'
_chemical_name_systematic
'N-(p-Hydroxy Benzylidene)phenylamine N-oxide'
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_audit_creation_method           SHELXL
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.033(9)
_cell_length_b                   14.019(9)
_cell_length_c                   8.973(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      25
_cell_measurement_theta_min      5
_cell_volume                     2268(2)
_computing_cell_refinement       TEXSAN
_computing_data_collection
'TEXSAN (Molecular Strucutre Corporation, 1989)'
_computing_data_reduction        TEXSAN
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Rigaku AFC-7S'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7071
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_av_sigmaI/netI    0.0956
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1875
_diffrn_reflns_theta_max         24.87
_diffrn_reflns_theta_min         4.89
_diffrn_standards_decay_%        negligible
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_type   '\y scan (North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.972
_refine_ls_goodness_of_fit_obs   1.043
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1874
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.972
_refine_ls_restrained_S_obs      1.043
_refine_ls_R_factor_all          0.146
_refine_ls_R_factor_obs          0.035
_refine_ls_shift/esd_max         0.048
_refine_ls_shift/esd_mean        0.013
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^) + (0.0407P)^2^] where P = (Fo^2^ + 2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.115
_refine_ls_wR_factor_obs         0.079
_reflns_number_observed          843
_reflns_number_total             1874
_reflns_observed_criterion       I>2\s(I)
_[local]_cod_data_source_file    de1054.cif
_[local]_cod_data_source_block   vps1a93
_cod_original_cell_volume        2269(2)
_cod_database_code               2006466
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z'
'-x, y-1/2, -z-1/2'
'x-1/2, y, -z-1/2'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O8 0.0612(11) 0.0501(9) 0.0449(10) -0.0018(8) 0.0089(9) -0.0073(8)
O4 0.0544(11) 0.0520(10) 0.0738(14) -0.0073(9) 0.0170(11) -0.0055(8)
N8 0.0448(12) 0.0461(11) 0.0367(11) 0.0006(9) -0.0013(11) -0.0011(10)
C4 0.0428(15) 0.0483(15) 0.051(2) 0.0030(12) 0.0003(14) 0.0044(13)
C7 0.0459(15) 0.0505(14) 0.0380(14) 0.0017(12) 0.0008(12) -0.0057(11)
C8 0.047(2) 0.0471(14) 0.0424(15) -0.0024(12) 0.0032(13) 0.0010(12)
C2 0.0512(14) 0.049(2) 0.061(2) -0.0032(12) 0.009(2) -0.0107(13)
C3 0.054(2) 0.052(2) 0.072(2) 0.0000(13) 0.020(2) -0.0133(13)
C1 0.0429(14) 0.0460(13) 0.0405(14) -0.0003(11) 0.0001(13) -0.0020(12)
C5 0.0512(15) 0.0422(12) 0.051(2) -0.0028(11) 0.0004(14) -0.0047(13)
C6 0.056(2) 0.0491(14) 0.0439(15) 0.0029(12) 0.0094(14) -0.0042(11)
C13 0.055(2) 0.070(2) 0.054(2) -0.0091(13) -0.001(2) 0.0005(14)
C9 0.071(2) 0.069(2) 0.047(2) -0.0118(15) 0.004(2) -0.0042(14)
C12 0.053(2) 0.089(2) 0.085(3) -0.015(2) 0.005(2) 0.000(2)
C11 0.060(2) 0.075(2) 0.092(3) -0.013(2) 0.025(2) 0.005(2)
C10 0.093(3) 0.077(2) 0.058(2) -0.011(2) 0.029(2) 0.0026(15)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_type_symbol
O8 0.62471(10) 0.14149(10) 0.1313(2) 0.0520(5) Uani d 1 O
O4 0.88404(10) 0.45819(10) 0.0815(2) 0.0601(5) Uani d 1 O
N8 0.60283(10) 0.18808(12) 0.2520(2) 0.0425(5) Uani d 1 N
C4 0.82362(14) 0.4123(2) 0.1350(3) 0.0473(6) Uani d 1 C
C7 0.63625(13) 0.2644(2) 0.3013(3) 0.0448(6) Uani d 1 C
C8 0.53572(14) 0.1539(2) 0.3225(3) 0.0456(6) Uani d 1 C
C2 0.7495(2) 0.2706(2) 0.1337(3) 0.0536(7) Uani d 1 C
C3 0.80965(15) 0.3209(2) 0.0834(3) 0.0593(8) Uani d 1 C
C1 0.70133(12) 0.3093(2) 0.2403(3) 0.0431(6) Uani d 1 C
C5 0.77657(13) 0.45249(15) 0.2404(3) 0.0480(6) Uani d 1 C
C6 0.71760(15) 0.4011(2) 0.2935(3) 0.0497(7) Uani d 1 C
C13 0.4787(2) 0.1236(2) 0.2323(3) 0.0599(7) Uani d 1 C
C9 0.5297(2) 0.1513(2) 0.4753(3) 0.0623(8) Uani d 1 C
C12 0.4139(2) 0.0935(2) 0.2974(4) 0.0756(9) Uani d 1 C
C11 0.4070(2) 0.0912(2) 0.4503(4) 0.0756(10) Uani d 1 C
C10 0.4643(2) 0.1200(2) 0.5395(4) 0.0761(10) Uani d 1 C
H7 0.6115 0.2935 0.3841 0.048 Uiso d 1 H
H6 0.6862 0.4253 0.3614 0.054 Uiso d 1 H
H4 0.6166 0.0233 0.1087 0.065 Uiso d 1 H
H2 0.7407 0.2096 0.0966 0.077 Uiso d 1 H
H10 0.4612 0.1159 0.6427 0.083 Uiso d 1 H
H5 0.7840 0.5164 0.2803 0.051 Uiso d 1 H
H3 0.8439 0.2950 0.0092 0.063 Uiso d 1 H
H13 0.4850 0.1268 0.1277 0.064 Uiso d 1 H
H11 0.3633 0.0696 0.4971 0.081 Uiso d 1 H
H12 0.3709 0.0770 0.2340 0.082 Uiso d 1 H
H9 0.5679 0.1648 0.5300 0.067 Uiso d 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 N8 O8 122.9(2) ?
C7 N8 C8 120.6(2) yes
O8 N8 C8 116.3(2) yes
O4 C4 C3 117.9(2) ?
O4 C4 C5 122.7(2) ?
C3 C4 C5 119.4(2) ?
N8 C7 C1 127.3(2) yes
N8 C7 H7 113.3(2) ?
C1 C7 H7 119.3(2) ?
C9 C8 C13 121.3(3) yes
C9 C8 N8 120.7(2) yes
C13 C8 N8 118.0(2) yes
C3 C2 C1 121.1(2) ?
C3 C2 H2 119.3(3) ?
C1 C2 H2 119.6(3) ?
C2 C3 C4 120.6(2) ?
C2 C3 H3 122.3(2) ?
C4 C3 H3 117.1(2) ?
C6 C1 C2 117.2(2) ?
C6 C1 C7 116.2(2) ?
C2 C1 C7 126.5(2) ?
C6 C5 C4 119.9(2) ?
C6 C5 H5 117.6(3) ?
C4 C5 H5 122.6(2) ?
C5 C6 C1 121.7(2) ?
C5 C6 H6 121.8(2) ?
C1 C6 H6 116.4(2) ?
C12 C13 C8 118.8(3) ?
C12 C13 H13 122.5(3) ?
C8 C13 H13 118.6(3) ?
C8 C9 C10 119.4(3) ?
C8 C9 H9 119.7(3) ?
C10 C9 H9 120.7(3) ?
C13 C12 C11 120.5(3) ?
C13 C12 H12 119.7(3) ?
C11 C12 H12 119.7(3) ?
C10 C11 C12 120.6(3) ?
C10 C11 H11 117.7(4) ?
C12 C11 H11 121.7(4) ?
C11 C10 C9 119.5(3) ?
C11 C10 H10 121.3(4) ?
C9 C10 H10 119.0(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O8 N8 1.325(2) ?
O4 C4 1.353(3) yes
N8 C7 1.304(3) ?
N8 C8 1.447(3) ?
C4 C3 1.386(3) yes
C4 C5 1.390(4) yes
C7 C1 1.440(3) ?
C7 H7 0.959(2) ?
C8 C9 1.376(4) yes
C8 C13 1.376(4) yes
C2 C3 1.370(4) yes
C2 C1 1.401(4) yes
C2 H2 0.931(2) ?
C3 H3 0.979(3) ?
C1 C6 1.404(3) yes
C5 C6 1.370(3) yes
C5 H5 0.975(2) ?
C6 H6 0.899(3) ?
C13 C12 1.373(4) yes
C13 H13 0.947(3) ?
C9 C10 1.385(4) yes
C9 H9 0.866(3) ?
C12 C11 1.378(5) yes
C12 H12 0.989(3) ?
C11 C10 1.368(5) yes
C11 H11 0.944(3) ?
C10 H10 0.929(3) ?
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
_geom_torsion_publ_flag
O8 N8 C7 C1 -1.8(4) yes
C8 N8 C7 C1 -177.4(2) yes
C7 N8 C8 C9 -43.2(3) yes
O8 N8 C8 C9 141.0(2) yes
C7 N8 C8 C13 137.3(2) yes
O8 N8 C8 C13 -38.6(3) yes
C1 C2 C3 C4 -1.2(4) ?
O4 C4 C3 C2 179.8(3) yes
C5 C4 C3 C2 1.0(4) ?
C3 C2 C1 C6 -0.3(4) ?
C3 C2 C1 C7 179.6(3) ?
N8 C7 C1 C6 167.1(2) yes
N8 C7 C1 C2 -12.8(4) yes
O4 C4 C5 C6 -178.0(2) yes
C3 C4 C5 C6 0.8(4) ?
C4 C5 C6 C1 -2.4(4) ?
C2 C1 C6 C5 2.1(4) ?
C7 C1 C6 C5 -177.8(2) ?
C9 C8 C13 C12 2.2(4) ?
N8 C8 C13 C12 -178.2(2) yes
C13 C8 C9 C10 -1.8(4) ?
N8 C8 C9 C10 178.7(2) yes
C8 C13 C12 C11 -1.7(4) ?
C13 C12 C11 C10 0.8(5) ?
C12 C11 C10 C9 -0.3(5) ?
C8 C9 C10 C11 0.7(5) ?
O8 N8 C7 H7 174.55(2) yes
C8 N8 C7 H7 -0.89(4) yes