#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2011344.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_2011344
loop_
_publ_author_name
'Vijayalakshmi, L.'
'Parthasarathi, V.'
'Manishanker, P.'
_publ_section_title
;
 <i>N</i>-(<i>p</i>-Chlorobenzylidene)phenylamine <i>N</i>-oxide
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              e403
_journal_page_last               e404
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C13 H10 Cl N O'
_chemical_formula_sum            'C13 H10 Cl N O'
_chemical_formula_weight         231.67
_chemical_name_common            \a-(4-Chlorophenyl)-N-phenylnitrone
_chemical_name_systematic
;
N-(p-Chlorobenzylidene)phenylamine N-oxide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.089(17)
_cell_angle_beta                 98.130(18)
_cell_angle_gamma                83.505(14)
_cell_formula_units_Z            4
_cell_length_a                   13.594(2)
_cell_length_b                   14.808(3)
_cell_length_c                   5.6110(15)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     1110.8(4)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structures Corporation, 1995a)
;
_computing_data_reduction
'TEXSAN (Molecular Structures Corporation, 1995b)'
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1983)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device_type  '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     .71069
_diffrn_reflns_av_R_equivalents  .044
_diffrn_reflns_av_sigmaI/netI    .0298
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4199
_diffrn_reflns_theta_full        24.86
_diffrn_reflns_theta_max         24.86
_diffrn_reflns_theta_min         2.16
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .319
_exptl_absorpt_correction_T_max  .990
_exptl_absorpt_correction_T_min  .927
_exptl_absorpt_correction_type   '\y scan'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       'Rectangular block'
_exptl_crystal_F_000             480
_exptl_crystal_size_max          .20
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .15
_refine_diff_density_max         .197
_refine_diff_density_min         -.185
_refine_ls_extinction_coef       .0105(17)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          .054
_refine_ls_R_factor_gt           .036
_refine_ls_shift/su_max          .028
_refine_ls_shift/su_mean         .005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0540P)^2^+0.3079P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_ref         .115
_reflns_number_gt                2936
_reflns_number_total             3914
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    qa0266.cif
_[local]_cod_data_source_block   I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2011344
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cl1 .08634(4) .37479(5) .49747(12) .0754(2) Uani d . 1 Cl
O7 .55717(10) .36277(11) 1.1074(2) .0628(4) Uani d . 1 O
C1 .42085(13) .37648(12) .6602(3) .0414(4) Uani d . 1 C
N7 .58725(11) .37073(10) .8998(3) .0436(4) Uani d . 1 N
C7 .52773(14) .37843(12) .6946(3) .0443(4) Uani d . 1 C
H7 .5572 .3859 .5573 .0597(14) Uiso calc R 1 H
C8 .69399(13) .37342(12) .9075(3) .0426(4) Uani d . 1 C
C11 .89717(15) .37876(15) .9362(4) .0587(5) Uani d . 1 C
H11 .9657 .3808 .9457 .0597(14) Uiso calc R 1 H
C6 .36746(14) .34128(13) .8289(3) .0459(4) Uani d . 1 C
H6 .4011 .3188 .9765 .0597(14) Uiso calc R 1 H
C10 .84620(15) .41711(15) 1.1144(4) .0554(5) Uani d . 1 C
H10 .8806 .4452 1.2437 .0597(14) Uiso calc R 1 H
C2 .36751(14) .41033(13) .4411(3) .0468(4) Uani d . 1 C
H2 .4020 .4327 .3263 .0597(14) Uiso calc R 1 H
C3 .26571(14) .41142(13) .3913(3) .0509(5) Uani d . 1 C
H3 .2311 .4356 .2464 .0597(14) Uiso calc R 1 H
C4 .21524(14) .37588(13) .5607(3) .0483(5) Uani d . 1 C
C5 .26572(14) .33987(13) .7768(3) .0500(5) Uani d . 1 C
H5 .2310 .3148 .8868 .0597(14) Uiso calc R 1 H
C13 .74442(15) .33390(13) .7271(3) .0510(5) Uani d . 1 C
H13 .7102 .3057 .5977 .0597(14) Uiso calc R 1 H
C9 .74453(14) .41396(14) 1.1015(3) .0491(5) Uani d . 1 C
H9 .7104 .4390 1.2228 .0597(14) Uiso calc R 1 H
C12 .84608(15) .33733(15) .7439(4) .0577(5) Uani d . 1 C
H12 .8806 .3114 .6244 .0597(14) Uiso calc R 1 H
Cl1A .05893(4) .13780(5) -.02480(12) .0789(2) Uani d . 1 Cl
N7A .55987(11) .12874(10) .3994(3) .0446(4) Uani d . 1 N
O7A .52828(11) .13979(12) .6064(2) .0683(4) Uani d . 1 O
C8A .66763(14) .12258(12) .4054(3) .0434(4) Uani d . 1 C
C7A .50223(14) .12091(12) .1950(3) .0450(4) Uani d . 1 C
H7A .5340 .1116 .0593 .0597(14) Uiso calc R 1 H
C6A .33154(14) .16178(13) .3207(3) .0470(4) Uani d . 1 C
H6A .3591 .1834 .4679 .0597(14) Uiso calc R 1 H
C1A .39456(13) .12514(12) .1576(3) .0412(4) Uani d . 1 C
C13A .70872(15) .15996(14) .2211(3) .0511(5) Uani d . 1 C
H13A .6676 .1889 .0903 .0597(14) Uiso calc R 1 H
C2A .35026(14) .09271(13) -.0612(3) .0464(4) Uani d . 1 C
H2A .3909 .0693 -.1720 .0597(14) Uiso calc R 1 H
C10A .83055(15) .07375(15) .6109(4) .0570(5) Uani d . 1 C
H10A .8718 .0446 .7412 .0597(14) Uiso calc R 1 H
C12A .81117(15) .15366(15) .2344(4) .0588(5) Uani d . 1 C
H12A .8394 .1788 .1120 .0597(14) Uiso calc R 1 H
C4A .18828(14) .13218(13) .0471(4) .0495(5) Uani d . 1 C
C9A .72788(15) .08020(14) .6017(3) .0504(5) Uani d . 1 C
H9A .6997 .0563 .7259 .0597(14) Uiso calc R 1 H
C5A .22948(14) .16580(13) .2635(3) .0503(5) Uani d . 1 C
H5A .1882 .1912 .3707 .0597(14) Uiso calc R 1 H
C3A .24824(15) .09455(14) -.1168(3) .0504(5) Uani d . 1 C
H3A .2200 .0711 -.2611 .0597(14) Uiso calc R 1 H
C11A .87240(15) .11036(15) .4277(4) .0585(5) Uani d . 1 C
H11A .9415 .1058 .4345 .0597(14) Uiso calc R 1 H
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
Cl1 .0402(3) .1010(5) .0847(4) -.0088(3) .0076(3) -.0126(3)
O7 .0505(8) .1047(12) .0353(7) -.0089(8) .0128(6) .0025(7)
C1 .0439(10) .0436(10) .0379(9) -.0068(8) .0086(7) -.0020(7)
N7 .0412(8) .0528(9) .0378(8) -.0055(7) .0095(6) -.0006(6)
C7 .0449(10) .0533(11) .0363(9) -.0078(8) .0098(8) .0011(8)
C8 .0421(10) .0464(10) .0395(9) -.0026(8) .0083(7) .0022(7)
C11 .0385(11) .0740(14) .0627(13) -.0037(10) .0059(9) .0022(11)
C6 .0491(11) .0498(11) .0402(9) -.0091(8) .0083(8) .0032(8)
C10 .0474(11) .0662(13) .0495(11) -.0053(9) -.0030(9) -.0051(9)
C2 .0493(11) .0548(11) .0383(9) -.0106(9) .0097(8) .0012(8)
C3 .0495(11) .0582(12) .0429(10) -.0037(9) .0019(8) -.0008(8)
C4 .0396(10) .0529(11) .0535(11) -.0072(8) .0087(8) -.0114(9)
C5 .0512(11) .0560(12) .0471(10) -.0136(9) .0156(9) -.0008(9)
C13 .0510(11) .0587(12) .0443(10) -.0068(9) .0103(8) -.0079(9)
C9 .0469(11) .0583(12) .0406(10) -.0009(9) .0057(8) -.0043(8)
C12 .0503(12) .0692(14) .0559(12) -.0010(10) .0197(9) -.0050(10)
Cl1A .0429(3) .1096(5) .0818(4) -.0063(3) .0022(3) .0008(4)
N7A .0447(9) .0534(9) .0376(8) -.0067(7) .0120(7) -.0012(6)
O7A .0529(9) .1166(13) .0369(7) -.0052(8) .0149(6) -.0075(7)
C8A .0447(10) .0465(10) .0403(9) -.0076(8) .0088(8) -.0044(8)
C7A .0478(10) .0518(11) .0373(9) -.0061(8) .0122(8) -.0028(8)
C6A .0510(11) .0523(11) .0385(9) -.0052(9) .0099(8) -.0049(8)
C1A .0452(10) .0425(10) .0374(9) -.0047(7) .0112(7) .0017(7)
C13A .0493(11) .0587(12) .0460(10) -.0084(9) .0074(8) .0061(9)
C2A .0497(11) .0519(11) .0390(9) -.0044(8) .0126(8) -.0025(8)
C10A .0526(12) .0661(13) .0501(11) -.0099(10) -.0028(9) .0038(9)
C12A .0535(12) .0756(15) .0522(12) -.0189(11) .0154(10) .0039(10)
C4A .0428(10) .0548(12) .0510(11) -.0051(9) .0073(8) .0062(9)
C9A .0528(11) .0598(12) .0399(10) -.0127(9) .0065(8) .0023(8)
C5A .0478(11) .0573(12) .0469(10) -.0005(9) .0150(9) -.0030(9)
C3A .0519(11) .0580(12) .0417(10) -.0108(9) .0040(8) -.0026(8)
C11A .0415(11) .0747(14) .0608(13) -.0137(10) .0062(9) -.0041(11)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl .1484 .1585 '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 118.17(17) ?
C2 C1 C7 117.28(16) ?
C6 C1 C7 124.54(16) ?
O7 N7 C7 124.13(15) yes
O7 N7 C8 115.32(14) yes
C7 N7 C8 120.52(14) yes
N7 C7 C1 126.45(16) ?
N7 C7 H7 116.8 ?
C1 C7 H7 116.8 ?
C9 C8 C13 120.94(18) ?
C9 C8 N7 118.13(16) yes
C13 C8 N7 120.91(16) yes
C12 C11 C10 119.82(19) ?
C12 C11 H11 120.1 ?
C10 C11 H11 120.1 ?
C5 C6 C1 120.33(17) ?
C5 C6 H6 119.8 ?
C1 C6 H6 119.8 ?
C9 C10 C11 120.33(19) ?
C9 C10 H10 119.8 ?
C11 C10 H10 119.8 ?
C3 C2 C1 121.67(17) ?
C3 C2 H2 119.2 ?
C1 C2 H2 119.2 ?
C2 C3 C4 118.81(18) ?
C2 C3 H3 120.6 ?
C4 C3 H3 120.6 ?
C5 C4 C3 121.15(17) ?
C5 C4 Cl1 119.53(15) ?
C3 C4 Cl1 119.31(15) yes
C6 C5 C4 119.83(17) ?
C6 C5 H5 120.1 ?
C4 C5 H5 120.1 ?
C12 C13 C8 118.73(18) ?
C12 C13 H13 120.6 ?
C8 C13 H13 120.6 ?
C8 C9 C10 119.43(18) ?
C8 C9 H9 120.3 ?
C10 C9 H9 120.3 ?
C13 C12 C11 120.74(19) ?
C13 C12 H12 119.6 ?
C11 C12 H12 119.6 ?
O7A N7A C7A 124.61(16) yes
O7A N7A C8A 115.50(14) yes
C7A N7A C8A 119.86(15) yes
C9A C8A C13A 120.98(18) ?
C9A C8A N7A 118.24(16) yes
C13A C8A N7A 120.76(16) yes
N7A C7A C1A 126.93(16) yes
N7A C7A H7A 116.5 ?
C1A C7A H7A 116.5 ?
C5A C6A C1A 120.38(17) ?
C5A C6A H6A 119.8 ?
C1A C6A H6A 119.8 ?
C2A C1A C6A 118.12(17) ?
C2A C1A C7A 116.88(16) ?
C6A C1A C7A 124.96(16) ?
C12A C13A C8A 119.09(18) ?
C12A C13A H13A 120.5 ?
C8A C13A H13A 120.5 ?
C3A C2A C1A 121.73(17) ?
C3A C2A H2A 119.1 ?
C1A C2A H2A 119.1 ?
C9A C10A C11A 120.41(19) ?
C9A C10A H10A 119.8 ?
C11A C10A H10A 119.8 ?
C13A C12A C11A 120.62(18) ?
C13A C12A H12A 119.7 ?
C11A C12A H12A 119.7 ?
C5A C4A C3A 121.19(18) ?
C5A C4A Cl1A 119.79(15) ?
C3A C4A Cl1A 119.01(15) ?
C8A C9A C10A 119.13(18) ?
C8A C9A H9A 120.4 ?
C10A C9A H9A 120.4 ?
C6A C5A C4A 119.98(17) ?
C6A C5A H5A 120.0 ?
C4A C5A H5A 120.0 ?
C2A C3A C4A 118.57(18) ?
C2A C3A H3A 120.7 ?
C4A C3A H3A 120.7 ?
C12A C11A C10A 119.75(19) ?
C12A C11A H11A 120.1 ?
C10A C11A H11A 120.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C4 1.7398(19) yes
O7 N7 1.2976(18) yes
C1 C2 1.398(2) yes
C1 C6 1.406(2) ?
C1 C7 1.442(2) ?
N7 C7 1.307(2) yes
N7 C8 1.451(2) yes
C7 H7 .9300 ?
C8 C9 1.377(3) yes
C8 C13 1.393(2) yes
C11 C12 1.380(3) yes
C11 C10 1.381(3) yes
C11 H11 .9300 ?
C6 C5 1.375(3) yes
C6 H6 .9300 ?
C10 C9 1.380(3) yes
C10 H10 .9300 ?
C2 C3 1.371(3) yes
C2 H2 .9300 ?
C3 C4 1.385(3) yes
C3 H3 .9300 ?
C4 C5 1.382(3) yes
C5 H5 .9300 ?
C13 C12 1.378(3) yes
C13 H13 .9300 ?
C9 H9 .9300 ?
C12 H12 .9300 ?
Cl1A C4A 1.7402(19) yes
N7A O7A 1.2980(19) yes
N7A C7A 1.307(2) yes
N7A C8A 1.453(2) yes
C8A C9A 1.381(3) yes
C8A C13A 1.387(3) yes
C7A C1A 1.443(2) yes
C7A H7A .9300 ?
C6A C5A 1.374(3) yes
C6A C1A 1.407(2) yes
C6A H6A .9300 ?
C1A C2A 1.398(3) yes
C13A C12A 1.377(3) yes
C13A H13A .9300 ?
C2A C3A 1.375(3) yes
C2A H2A .9300 ?
C10A C9A 1.382(3) yes
C10A C11A 1.383(3) yes
C10A H10A .9300 ?
C12A C11A 1.381(3) yes
C12A H12A .9300 ?
C4A C5A 1.380(3) yes
C4A C3A 1.389(3) yes
C9A H9A .9300 ?
C5A H5A .9300 ?
C3A H3A .9300 ?
C11A H11A .9300 ?
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
O7 N7 C7 C1 -2.2(3) yes
C8 N7 C7 C1 179.65(16) yes
C2 C1 C7 N7 162.77(18) yes
C6 C1 C7 N7 -18.6(3) yes
O7 N7 C8 C9 -33.4(2) yes
C7 N7 C8 C9 144.82(18) yes
O7 N7 C8 C13 144.82(18) yes
C7 N7 C8 C13 -36.9(3) yes
C2 C1 C6 C5 .6(3) ?
C7 C1 C6 C5 -178.03(18) ?
C12 C11 C10 C9 .2(3) ?
C6 C1 C2 C3 1.3(3) ?
C7 C1 C2 C3 -179.98(17) ?
C1 C2 C3 C4 -1.7(3) ?
C2 C3 C4 C5 .1(3) ?
C2 C3 C4 Cl1 -178.75(15) ?
C1 C6 C5 C4 -2.1(3) ?
C3 C4 C5 C6 1.8(3) ?
Cl1 C4 C5 C6 -179.40(15) ?
C9 C8 C13 C12 -1.0(3) ?
N7 C8 C13 C12 -179.26(17) yes
C13 C8 C9 C10 1.4(3) ?
N7 C8 C9 C10 179.66(17) yes
C11 C10 C9 C8 -1.0(3) ?
C8 C13 C12 C11 .3(3) ?
C10 C11 C12 C13 .1(3) ?
O7A N7A C8A C9A 34.9(2) yes
C7A N7A C8A C9A -143.41(19) yes
O7A N7A C8A C13A -143.76(19) yes
C7A N7A C8A C13A 37.9(3) yes
O7A N7A C7A C1A 1.7(3) yes
C8A N7A C7A C1A 179.87(16) yes
C5A C6A C1A C2A -.5(3) ?
C5A C6A C1A C7A 177.43(18) ?
N7A C7A C1A C2A -164.33(18) yes
N7A C7A C1A C6A 17.7(3) yes
C9A C8A C13A C12A .6(3) ?
N7A C8A C13A C12A 179.28(18) yes
C6A C1A C2A C3A -1.1(3) ?
C7A C1A C2A C3A -179.20(17) ?
C8A C13A C12A C11A .3(3) ?
C13A C8A C9A C10A -1.2(3) ?
N7A C8A C9A C10A -179.92(17) yes
C11A C10A C9A C8A .9(3) ?
C1A C6A C5A C4A 1.3(3) ?
C3A C4A C5A C6A -.5(3) ?
Cl1A C4A C5A C6A -179.78(15) ?
C1A C2A C3A C4A 1.9(3) ?
C5A C4A C3A C2A -1.1(3) ?
Cl1A C4A C3A C2A 178.23(15) ?
C13A C12A C11A C10A -.7(3) ?
C9A C10A C11A C12A .0(3) ?