##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
N-(2-Nitrobenzylidene)aniline
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H10 N2 O2'
_chemical_formula_sum     'C13 H10 N2 O2'
_chemical_formula_iupac     'C13 H10 N2 O2'
_chemical_formula_weight     226.23
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    x,y,z
    -x,1/2+y,1/2-z
    -x,-y,-z
    x,1/2-y,1/2+z
_cell_length_a     11.178(13)
_cell_length_b     7.718(5)
_cell_length_c     13.217(16)
_cell_angle_alpha     90
_cell_angle_beta     94.064(3)
_cell_angle_gamma     90
_cell_volume     1137(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3583
_cell_measurement_theta_min     3.06
_cell_measurement_theta_max     25.02
_cell_measurement_temperature     295(2)
_exptl_crystal_description     block
_exptl_crystal_colour     'pale yellow'
_exptl_crystal_size_max     0.250
_exptl_crystal_size_mid     0.23
_exptl_crystal_size_min     0.22
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.321
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     472
_exptl_absorpt_coefficient_mu     0.091
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     none
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     295(2)
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'MacScience DIPLabo 32001'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     10.0
_diffrn_reflns_number     3583
_diffrn_reflns_av_R_equivalents     0.0196
_diffrn_reflns_av_sigmaI/netI     0.0251
_diffrn_reflns_theta_min     3.06
_diffrn_reflns_theta_max     25.02
_diffrn_reflns_theta_full     25.02
_diffrn_measured_fraction_theta_max     0.961
_diffrn_measured_fraction_theta_full     0.961
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     0
_refine_special_details
;
 Refinement on F\^2 for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F\^2, conventional R-factors R are based
 on F, with F set to zero for negative F\^2. The
 observed criterion of F\^2 > 2sigma(F\^2) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F\^2 are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_reflns_number_total     1923
_reflns_number_gt     1555
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0611
_refine_ls_R_factor_gt     0.0509
_refine_ls_wR_factor_gt     0.1516
_refine_ls_wR_factor_ref     0.1720
_refine_ls_goodness_of_fit_ref     1.005
_refine_ls_restrained_S_all     1.005
_refine_ls_number_reflns     1923
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.1279P)²+0.0772P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.266
_refine_diff_density_min     -0.162
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_extinction_coef     0.081(12)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    O O 0.0106 0.0060 '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'
    H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'XPRESS (MacScience, 2002)'
_computing_cell_refinement     'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO (Otwinowski & Minor, 1997) and SCALEPACK'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
                               'PLATON (Spek, 2003) and ORTEPII (Johnson, 1976)'
_computing_publication_material     'PLATON'
loop_
    _atom_site_type_symbol
    _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_refinement_flags
    _atom_site_occupancy
    O O8 0.00571(14) 0.1380(3) 0.09731(14) 0.0931(7) Uani . . 1.000
    O O9 0.16962(13) -0.0031(2) 0.09510(13) 0.0771(6) Uani . . 1.000
    N N7 0.10594(15) 0.1188(2) 0.06905(12) 0.0619(6) Uani . . 1.000
    N N11 0.47063(13) 0.23753(19) 0.06941(11) 0.0519(5) Uani . . 1.000
    C C1 0.2230(2) 0.4690(3) -0.14600(16) 0.0670(7) Uani . . 1.000
    C C2 0.30484(18) 0.4046(2) -0.07250(14) 0.0580(7) Uani . . 1.000
    C C3 0.27086(15) 0.2895(2) 0.00127(13) 0.0496(6) Uani . . 1.000
    C C4 0.14966(16) 0.2461(2) -0.00221(14) 0.0521(6) Uani . . 1.000
    C C5 0.06591(18) 0.3115(3) -0.07450(16) 0.0634(7) Uani . . 1.000
    C C6 0.1037(2) 0.4228(3) -0.14711(17) 0.0693(8) Uani . . 1.000
    C C10 0.35996(15) 0.2297(2) 0.08162(13) 0.0499(6) Uani . . 1.000
    C C12 0.55308(15) 0.1916(2) 0.15159(13) 0.0476(5) Uani . . 1.000
    C C13 0.65628(16) 0.1045(2) 0.12956(14) 0.0549(6) Uani . . 1.000
    C C14 0.74091(17) 0.0600(3) 0.20630(17) 0.0627(7) Uani . . 1.000
    C C15 0.72453(18) 0.1057(3) 0.30544(16) 0.0630(7) Uani . . 1.000
    C C16 0.62333(18) 0.1939(3) 0.32780(15) 0.0633(7) Uani . . 1.000
    C C17 0.53740(16) 0.2378(2) 0.25167(14) 0.0555(6) Uani . . 1.000
    H H1 0.24840 0.54410 -0.19520 0.0800 Uiso calc R 1.000
    H H2 0.38460 0.43890 -0.07220 0.0700 Uiso calc R 1.000
    H H5 -0.01450 0.28070 -0.07400 0.0760 Uiso calc R 1.000
    H H6 0.04890 0.46680 -0.19680 0.0830 Uiso calc R 1.000
    H H10 0.33410 0.18580 0.14190 0.0600 Uiso calc R 1.000
    H H13 0.66870 0.07580 0.06280 0.0660 Uiso calc R 1.000
    H H14 0.80920 -0.00090 0.19120 0.0750 Uiso calc R 1.000
    H H15 0.78210 0.07670 0.35690 0.0760 Uiso calc R 1.000
    H H16 0.61240 0.22450 0.39460 0.0760 Uiso calc R 1.000
    H H17 0.46910 0.29810 0.26730 0.0670 Uiso calc R 1.000
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 0.0592(10) 0.1275(15) 0.0953(13) -0.0015(9) 0.0242(9) 0.0218(10)
    O9 0.0669(9) 0.0745(9) 0.0888(11) -0.0078(7) -0.0028(8) 0.0227(8)
    N7 0.0491(10) 0.0767(11) 0.0595(10) -0.0090(8) 0.0016(7) 0.0053(8)
    N11 0.0466(9) 0.0608(9) 0.0483(9) -0.0007(6) 0.0039(6) -0.0015(6)
    C1 0.0759(14) 0.0638(12) 0.0603(12) -0.0059(9) -0.0026(10) 0.0104(9)
    C2 0.0583(12) 0.0603(11) 0.0552(11) -0.0094(8) 0.0023(9) 0.0019(8)
    C3 0.0490(10) 0.0537(9) 0.0459(10) -0.0028(7) 0.0010(7) -0.0050(7)
    C4 0.0491(10) 0.0559(10) 0.0512(10) -0.0015(7) 0.0034(8) -0.0012(7)
    C5 0.0478(11) 0.0713(13) 0.0698(13) 0.0012(8) -0.0044(9) 0.0037(10)
    C6 0.0676(14) 0.0717(13) 0.0663(13) 0.0022(10) -0.0110(10) 0.0085(10)
    C10 0.0483(10) 0.0550(10) 0.0462(10) -0.0057(7) 0.0028(7) -0.0013(7)
    C12 0.0428(9) 0.0520(9) 0.0483(10) -0.0068(7) 0.0050(7) 0.0003(7)
    C13 0.0509(11) 0.0620(11) 0.0526(11) 0.0004(7) 0.0093(8) -0.0027(8)
    C14 0.0482(11) 0.0643(11) 0.0759(14) 0.0042(8) 0.0055(9) 0.0040(9)
    C15 0.0518(12) 0.0698(13) 0.0659(13) -0.0104(8) -0.0066(9) 0.0135(9)
    C16 0.0621(12) 0.0806(13) 0.0469(11) -0.0122(10) 0.0023(9) -0.0030(9)
    C17 0.0477(10) 0.0669(11) 0.0524(11) -0.0025(8) 0.0068(8) -0.0071(8)
_geom_special_details
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All esds are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O8 N7 . . 1.215(2) yes
    O9 N7 . . 1.215(2) yes
    N7 C4 . . 1.468(2) yes
    N11 C10 . . 1.260(2) yes
    N11 C12 . . 1.419(2) yes
    C1 C2 . . 1.379(3) no
    C1 C6 . . 1.379(3) no
    C2 C3 . . 1.392(2) no
    C3 C4 . . 1.393(2) no
    C3 C10 . . 1.477(2) no
    C4 C5 . . 1.385(3) no
    C5 C6 . . 1.377(3) no
    C12 C13 . . 1.384(2) no
    C12 C17 . . 1.393(3) no
    C13 C14 . . 1.380(3) no
    C14 C15 . . 1.382(3) no
    C15 C16 . . 1.370(3) no
    C16 C17 . . 1.383(3) no
    C1 H1 . . 0.9304 no
    C2 H2 . . 0.9298 no
    C5 H5 . . 0.9302 no
    C6 H6 . . 0.9300 no
    C10 H10 . . 0.9305 no
    C13 H13 . . 0.9297 no
    C14 H14 . . 0.9301 no
    C15 H15 . . 0.9299 no
    C16 H16 . . 0.9303 no
    C17 H17 . . 0.9298 no
loop_
    _geom_contact_atom_site_label_1
    _geom_contact_atom_site_label_2
    _geom_contact_distance
    _geom_contact_site_symmetry_1
    _geom_contact_site_symmetry_2
    _geom_contact_publ_flag
    O8 N7 3.151(3) . 3_555 no
    O9 C16 3.396(3) . 2_645 no
    O9 C10 2.800(2) . . no
    O8 H5 2.5136 . . no
    O8 H14 2.8108 . 1_455 no
    O8 H6 2.8472 . 4_555 no
    O9 H10 2.3932 . . no
    O9 H5 2.7579 . 3_555 no
    O9 H13 2.9105 . 3_655 no
    O9 H1 2.8656 . 4_555 no
    N7 O8 3.151(3) . 3_555 no
    N7 H10 2.7112 . . no
    N11 H2 2.5668 . . no
    N11 H16 2.9076 . 4_554 no
    C1 C13 3.558(3) . 3_665 no
    C3 C15 3.531(3) . 2_655 no
    C10 C15 3.427(3) . 2_655 no
    C10 O9 2.800(2) . . no
    C13 C1 3.558(3) . 3_665 no
    C15 C3 3.531(3) . 2_645 no
    C15 C10 3.427(3) . 2_645 no
    C16 O9 3.396(3) . 2_655 no
    C3 H13 3.0337 . 3_655 no
    C3 H15 2.9892 . 2_655 no
    C10 H13 3.0363 . 3_655 no
    C10 H17 2.7139 . . no
    C12 H1 3.0391 . 3_665 no
    C13 H1 3.0187 . 3_665 no
    C14 H1 3.0618 . 3_665 no
    C15 H1 3.0955 . 3_665 no
    C16 H1 3.0939 . 3_665 no
    C17 H10 2.6387 . . no
    C17 H1 3.0621 . 3_665 no
    H1 C12 3.0391 . 3_665 no
    H1 C13 3.0187 . 3_665 no
    H1 C14 3.0618 . 3_665 no
    H1 C15 3.0955 . 3_665 no
    H1 C16 3.0939 . 3_665 no
    H1 C17 3.0621 . 3_665 no
    H1 O9 2.8656 . 4_554 no
    H2 N11 2.5668 . . no
    H5 O8 2.5136 . . no
    H5 O9 2.7579 . 3_555 no
    H6 O8 2.8472 . 4_554 no
    H10 O9 2.3932 . . no
    H10 N7 2.7112 . . no
    H10 C17 2.6387 . . no
    H10 H17 2.3283 . . no
    H13 O9 2.9105 . 3_655 no
    H13 C3 3.0337 . 3_655 no
    H13 C10 3.0363 . 3_655 no
    H14 O8 2.8108 . 1_655 no
    H15 C3 2.9892 . 2_645 no
    H16 N11 2.9076 . 4_555 no
    H17 C10 2.7139 . . no
    H17 H10 2.3283 . . no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O8 N7 O9 . . . 122.82(18) yes
    O8 N7 C4 . . . 118.14(17) yes
    O9 N7 C4 . . . 119.01(16) yes
    C10 N11 C12 . . . 118.70(15) yes
    C2 C1 C6 . . . 120.5(2) no
    C1 C2 C3 . . . 121.55(18) no
    C2 C3 C4 . . . 116.32(16) no
    C2 C3 C10 . . . 119.97(16) no
    C4 C3 C10 . . . 123.58(15) no
    N7 C4 C3 . . . 120.45(15) yes
    N7 C4 C5 . . . 116.55(16) yes
    C3 C4 C5 . . . 122.92(17) no
    C4 C5 C6 . . . 118.86(19) no
    C1 C6 C5 . . . 119.9(2) no
    N11 C10 C3 . . . 120.72(15) yes
    N11 C12 C13 . . . 117.79(15) yes
    N11 C12 C17 . . . 122.98(15) yes
    C13 C12 C17 . . . 119.14(16) no
    C12 C13 C14 . . . 120.29(17) no
    C13 C14 C15 . . . 120.22(19) no
    C14 C15 C16 . . . 119.89(19) no
    C15 C16 C17 . . . 120.41(18) no
    C12 C17 C16 . . . 120.03(17) no
    C2 C1 H1 . . . 119.79 no
    C6 C1 H1 . . . 119.75 no
    C1 C2 H2 . . . 119.24 no
    C3 C2 H2 . . . 119.21 no
    C4 C5 H5 . . . 120.55 no
    C6 C5 H5 . . . 120.59 no
    C1 C6 H6 . . . 120.07 no
    C5 C6 H6 . . . 120.06 no
    N11 C10 H10 . . . 119.63 no
    C3 C10 H10 . . . 119.65 no
    C12 C13 H13 . . . 119.88 no
    C14 C13 H13 . . . 119.83 no
    C13 C14 H14 . . . 119.88 no
    C15 C14 H14 . . . 119.90 no
    C14 C15 H15 . . . 120.06 no
    C16 C15 H15 . . . 120.06 no
    C15 C16 H16 . . . 119.78 no
    C17 C16 H16 . . . 119.81 no
    C12 C17 H17 . . . 119.98 no
    C16 C17 H17 . . . 119.99 no
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_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O8 N7 C4 C3 . . . . 146.97(18) no
    O9 N7 C4 C3 . . . . -35.0(2) no
    O8 N7 C4 C5 . . . . -36.2(2) no
    O9 N7 C4 C5 . . . . 141.83(19) no
    C10 N11 C12 C13 . . . . 143.06(16) no
    C12 N11 C10 C3 . . . . 175.05(14) no
    C10 N11 C12 C17 . . . . -40.3(2) no
    C2 C1 C6 C5 . . . . -0.1(3) no
    C6 C1 C2 C3 . . . . 1.2(3) no
    C1 C2 C3 C10 . . . . -177.14(17) no
    C1 C2 C3 C4 . . . . -1.2(3) no
    C4 C3 C10 N11 . . . . 163.25(16) no
    C10 C3 C4 N7 . . . . -7.4(2) no
    C2 C3 C10 N11 . . . . -21.2(2) no
    C2 C3 C4 C5 . . . . 0.2(3) no
    C2 C3 C4 N7 . . . . 176.84(15) no
    C10 C3 C4 C5 . . . . 175.99(17) no
    C3 C4 C5 C6 . . . . 0.8(3) no
    N7 C4 C5 C6 . . . . -175.91(18) no
    C4 C5 C6 C1 . . . . -0.9(3) no
    N11 C12 C13 C14 . . . . 178.56(16) no
    N11 C12 C17 C16 . . . . -177.79(17) no
    C13 C12 C17 C16 . . . . -1.2(2) no
    C17 C12 C13 C14 . . . . 1.7(3) no
    C12 C13 C14 C15 . . . . -1.5(3) no
    C13 C14 C15 C16 . . . . 0.7(3) no
    C14 C15 C16 C17 . . . . -0.1(3) no
    C15 C16 C17 C12 . . . . 0.3(3) no
data_global
_journal_date_recd_electronic     2006-08-07
_journal_date_accepted     2006-08-08
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      9
_journal_page_first     o3790
_journal_page_last     o3791
_journal_paper_category     EO
_journal_coeditor_code     AT2080
_publ_contact_author_name     'Dr M. A. Sridhar'
_publ_contact_author_address
;
Department of Studies in Physics
Mansagangotri
University of Mysore
Mysore 570 006
India
;
_publ_contact_author_email     mas@physics.uni-mysore.ac.in
_publ_contact_author_fax     '+91 821 2419333'
_publ_contact_author_phone     '+91 821 2419333'
_publ_section_title
;
N-(2-Nitrobenzylidene)aniline
;
loop_
    _publ_author_name
    _publ_author_address
    'Naveen, S.'
;
Department of Studies in Physics
Mansagangotri
University of Mysore
Mysore 570 006
India
;
    'Anil Kumar, K.'
;
Department of Studies in Chemistry
Mansagangotri
University of Mysore
Mysore 570 006
India
;
    'Channe Gowda, D.'
;
Department of Studies in Chemistry
Mansagangotri
University of Mysore
Mysore 570 006
India
;
    'Sridhar, M. A.'
;
Department of Studies in Physics
Mansagangotri
University of Mysore
Mysore 570 006
India
;
    'Shashidhara Prasad, J.'
;
Department of Studies in Physics
Mansagangotri
University of Mysore
Mysore 570 006
India
;
