##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
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data_global
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2010-10-15
_journal_date_accepted     2010-10-27
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue     12
_journal_page_first     o3288
_journal_page_last     o3288
_journal_paper_category     QO
_journal_coeditor_code     DN2613
_publ_contact_author_name     ' Wang Yong '
_publ_contact_author_address
;
School of Pharmaceutical and Chemical Engineering
Taizhou University
Linhai 317000
China
;
_publ_contact_author_email     yutaitang@hotmail.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
4-Anilino-3-nitrobenzonitrile
;
loop_
    _publ_author_name
    _publ_author_address
    'Wang, Yong'
;
School of Pharmaceutical and Chemical Engineering
Taizhou University
Linhai 317000
People's Republic of China
;
    'Fan, Kaiqing'
;
Agronomy  Department
Jiangsu Polytechnic College of Agriculture and Forestry
Jurong  212400 Jiangsu
People's Republic of China
;
    'Li, Chenghong'
;
School of Pharmaceutical and Chemical Engineering
Taizhou University
Linhai 317000
People's Republic of China
;
    'Ge, Changhua'
;
School of Pharmaceutical and Chemical Engineering
Taizhou University
Linhai 317000
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4-Anilino-3-nitrobenzonitrile
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H9 N3 O2'
_chemical_formula_sum     'C13 H9 N3 O2'
_chemical_formula_iupac     'C13 H9 N3 O2'
_chemical_formula_weight     239.23
_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, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     14.066(3)
_cell_length_b     7.4290(15)
_cell_length_c     11.652(2)
_cell_angle_alpha     90.00
_cell_angle_beta     109.04(3)
_cell_angle_gamma     90.00
_cell_volume     1151.0(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     9
_cell_measurement_theta_max     13
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.381
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     496
_exptl_absorpt_coefficient_mu     0.097
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al., 1968)'
_exptl_absorpt_correction_T_min     0.9715
_exptl_absorpt_correction_T_max     0.9904
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(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     'Enraf--Nonius CAD-4'
_diffrn_measurement_method     ω/2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4199
_diffrn_reflns_av_R_equivalents     0.0299
_diffrn_reflns_av_sigmaI/netI     0.0290
_diffrn_reflns_theta_min     1.53
_diffrn_reflns_theta_max     25.28
_diffrn_reflns_theta_full     25.28
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     3
_diffrn_standards_interval_count     200
_diffrn_standards_interval_time     120
_diffrn_standards_decay_%     1
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² 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     2082
_reflns_number_gt     1546
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0576
_refine_ls_R_factor_gt     0.0403
_refine_ls_wR_factor_gt     0.0978
_refine_ls_wR_factor_ref     0.1068
_refine_ls_goodness_of_fit_ref     1.041
_refine_ls_restrained_S_all     1.041
_refine_ls_number_reflns     2082
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0511P)²+0.1451P] 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     0.194
_refine_diff_density_min     -0.160
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_cell_refinement     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction     'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia,
1997) and
PLATON (Spek, 2009)
;
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.91767(8) 0.4271(2) 0.39718(10) 0.0665(4) Uani d . 1 . .
    O O2 0.84253(9) 0.43363(19) 0.20463(10) 0.0659(4) Uani d . 1 . .
    N N1 0.82164(10) 0.5168(2) 0.54802(11) 0.0545(4) Uani d . 1 . .
    H H1 0.8774 0.4845 0.5388 0.065 Uiso calc R 1 . .
    N N2 0.84229(10) 0.45587(19) 0.30832(11) 0.0485(4) Uani d . 1 . .
    N N3 0.43509(11) 0.6904(2) 0.03546(14) 0.0699(5) Uani d . 1 . .
    C C1 0.74708(13) 0.4539(2) 0.70743(15) 0.0570(5) Uani d . 1 . .
    H H1B 0.6921 0.3979 0.6517 0.068 Uiso calc R 1 . .
    C C2 0.75504(15) 0.4625(3) 0.82822(17) 0.0669(5) Uani d . 1 . .
    H H2A 0.7042 0.4143 0.8535 0.080 Uiso calc R 1 . .
    C C3 0.83667(16) 0.5411(3) 0.91186(16) 0.0695(6) Uani d . 1 . .
    H H3A 0.8414 0.5451 0.9933 0.083 Uiso calc R 1 . .
    C C4 0.91129(15) 0.6136(3) 0.87473(16) 0.0656(5) Uani d . 1 . .
    H H4A 0.9671 0.6659 0.9314 0.079 Uiso calc R 1 . .
    C C5 0.90432(12) 0.6097(3) 0.75389(14) 0.0537(4) Uani d . 1 . .
    H H5A 0.9548 0.6605 0.7290 0.064 Uiso calc R 1 . .
    C C6 0.82202(11) 0.5299(2) 0.67003(13) 0.0463(4) Uani d . 1 . .
    C C7 0.74482(11) 0.5487(2) 0.44502(13) 0.0438(4) Uani d . 1 . .
    C C8 0.65218(12) 0.6207(2) 0.44808(14) 0.0489(4) Uani d . 1 . .
    H H8A 0.6447 0.6444 0.5230 0.059 Uiso calc R 1 . .
    C C9 0.57426(12) 0.6561(2) 0.34586(14) 0.0506(4) Uani d . 1 . .
    H H9A 0.5150 0.7039 0.3520 0.061 Uiso calc R 1 . .
    C C10 0.58206(11) 0.6214(2) 0.23110(14) 0.0461(4) Uani d . 1 . .
    C C11 0.67092(11) 0.5533(2) 0.22313(13) 0.0455(4) Uani d . 1 . .
    H H11A 0.6771 0.5300 0.1474 0.055 Uiso calc R 1 . .
    C C12 0.75095(11) 0.5196(2) 0.32739(13) 0.0432(4) Uani d . 1 . .
    C C13 0.49993(12) 0.6596(2) 0.12224(15) 0.0524(4) Uani d . 1 . .
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
    O1 0.0436(7) 0.1033(11) 0.0496(7) 0.0174(7) 0.0112(5) -0.0019(6)
    O2 0.0553(7) 0.1003(11) 0.0471(7) 0.0071(7) 0.0237(6) -0.0053(6)
    N1 0.0437(7) 0.0796(11) 0.0403(7) 0.0117(7) 0.0140(6) 0.0013(7)
    N2 0.0431(7) 0.0617(9) 0.0421(7) 0.0019(7) 0.0157(6) -0.0028(6)
    N3 0.0545(9) 0.0920(13) 0.0557(9) 0.0140(9) 0.0076(8) 0.0037(9)
    C1 0.0556(10) 0.0621(11) 0.0535(10) -0.0002(9) 0.0182(8) 0.0053(9)
    C2 0.0700(12) 0.0752(13) 0.0661(12) 0.0131(11) 0.0369(10) 0.0185(10)
    C3 0.0884(15) 0.0803(14) 0.0438(10) 0.0311(12) 0.0268(10) 0.0111(9)
    C4 0.0634(11) 0.0753(13) 0.0466(10) 0.0174(10) 0.0022(9) -0.0035(9)
    C5 0.0428(9) 0.0686(11) 0.0476(9) 0.0092(8) 0.0120(7) 0.0026(8)
    C6 0.0449(8) 0.0540(10) 0.0394(8) 0.0119(8) 0.0130(7) 0.0038(7)
    C7 0.0430(8) 0.0468(9) 0.0418(8) -0.0007(7) 0.0140(7) -0.0001(7)
    C8 0.0485(9) 0.0578(10) 0.0431(9) 0.0042(8) 0.0189(7) -0.0009(8)
    C9 0.0431(9) 0.0561(10) 0.0543(10) 0.0058(8) 0.0181(8) 0.0022(8)
    C10 0.0395(8) 0.0509(10) 0.0450(9) -0.0007(7) 0.0102(7) 0.0020(7)
    C11 0.0461(9) 0.0509(10) 0.0394(8) -0.0027(7) 0.0140(7) -0.0013(7)
    C12 0.0389(8) 0.0472(9) 0.0442(8) 0.0013(7) 0.0144(7) -0.0013(7)
    C13 0.0449(9) 0.0615(11) 0.0502(9) 0.0041(8) 0.0148(8) 0.0021(8)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 N2 . 1.2352(16) ?
    O2 N2 . 1.2206(16) ?
    N1 C7 . 1.3483(18) ?
    N1 C6 . 1.4232(19) ?
    N1 H1 . 0.8600 ?
    N2 C12 . 1.4529(19) ?
    N3 C13 . 1.142(2) ?
    C1 C2 . 1.377(2) ?
    C1 C6 . 1.385(2) ?
    C1 H1B . 0.9300 ?
    C2 C3 . 1.371(3) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.369(3) ?
    C3 H3A . 0.9300 ?
    C4 C5 . 1.379(2) ?
    C4 H4A . 0.9300 ?
    C5 C6 . 1.382(2) ?
    C5 H5A . 0.9300 ?
    C7 C12 . 1.418(2) ?
    C7 C8 . 1.420(2) ?
    C8 C9 . 1.356(2) ?
    C8 H8A . 0.9300 ?
    C9 C10 . 1.401(2) ?
    C9 H9A . 0.9300 ?
    C10 C11 . 1.379(2) ?
    C10 C13 . 1.438(2) ?
    C11 C12 . 1.383(2) ?
    C11 H11A . 0.9300 ?
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_3
    _geom_angle
    _geom_angle_publ_flag
    C7 N1 C6 . . 128.16(14) ?
    C7 N1 H1 . . 115.9 ?
    C6 N1 H1 . . 115.9 ?
    O2 N2 O1 . . 121.83(13) ?
    O2 N2 C12 . . 118.93(13) ?
    O1 N2 C12 . . 119.24(13) ?
    C2 C1 C6 . . 119.09(17) ?
    C2 C1 H1B . . 120.5 ?
    C6 C1 H1B . . 120.5 ?
    C3 C2 C1 . . 121.11(18) ?
    C3 C2 H2A . . 119.4 ?
    C1 C2 H2A . . 119.4 ?
    C4 C3 C2 . . 119.57(17) ?
    C4 C3 H3A . . 120.2 ?
    C2 C3 H3A . . 120.2 ?
    C3 C4 C5 . . 120.51(18) ?
    C3 C4 H4A . . 119.7 ?
    C5 C4 H4A . . 119.7 ?
    C4 C5 C6 . . 119.68(18) ?
    C4 C5 H5A . . 120.2 ?
    C6 C5 H5A . . 120.2 ?
    C5 C6 C1 . . 120.02(15) ?
    C5 C6 N1 . . 117.71(15) ?
    C1 C6 N1 . . 122.08(15) ?
    N1 C7 C12 . . 123.37(14) ?
    N1 C7 C8 . . 121.29(14) ?
    C12 C7 C8 . . 115.30(14) ?
    C9 C8 C7 . . 122.46(15) ?
    C9 C8 H8A . . 118.8 ?
    C7 C8 H8A . . 118.8 ?
    C8 C9 C10 . . 120.70(15) ?
    C8 C9 H9A . . 119.7 ?
    C10 C9 H9A . . 119.7 ?
    C11 C10 C9 . . 119.11(14) ?
    C11 C10 C13 . . 119.86(15) ?
    C9 C10 C13 . . 121.01(15) ?
    C10 C11 C12 . . 120.19(15) ?
    C10 C11 H11A . . 119.9 ?
    C12 C11 H11A . . 119.9 ?
    C11 C12 C7 . . 122.20(14) ?
    C11 C12 N2 . . 115.57(13) ?
    C7 C12 N2 . . 122.22(13) ?
    N3 C13 C10 . . 179.6(2) ?
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
    C6 C1 C2 C3 . . . . -1.5(3) ?
    C1 C2 C3 C4 . . . . 0.5(3) ?
    C2 C3 C4 C5 . . . . 0.7(3) ?
    C3 C4 C5 C6 . . . . -0.8(3) ?
    C4 C5 C6 C1 . . . . -0.1(3) ?
    C4 C5 C6 N1 . . . . -175.33(16) ?
    C2 C1 C6 C5 . . . . 1.3(3) ?
    C2 C1 C6 N1 . . . . 176.26(16) ?
    C7 N1 C6 C5 . . . . -137.13(18) ?
    C7 N1 C6 C1 . . . . 47.8(3) ?
    C6 N1 C7 C12 . . . . -175.60(16) ?
    C6 N1 C7 C8 . . . . 6.6(3) ?
    N1 C7 C8 C9 . . . . 179.15(16) ?
    C12 C7 C8 C9 . . . . 1.2(2) ?
    C7 C8 C9 C10 . . . . 0.4(3) ?
    C8 C9 C10 C11 . . . . -1.1(3) ?
    C8 C9 C10 C13 . . . . -179.63(16) ?
    C9 C10 C11 C12 . . . . 0.1(2) ?
    C13 C10 C11 C12 . . . . 178.70(15) ?
    C10 C11 C12 C7 . . . . 1.5(2) ?
    C10 C11 C12 N2 . . . . -177.32(14) ?
    N1 C7 C12 C11 . . . . 179.94(15) ?
    C8 C7 C12 C11 . . . . -2.1(2) ?
    N1 C7 C12 N2 . . . . -1.3(2) ?
    C8 C7 C12 N2 . . . . 176.63(15) ?
    O2 N2 C12 C11 . . . . -1.2(2) ?
    O1 N2 C12 C11 . . . . 178.27(15) ?
    O2 N2 C12 C7 . . . . 180.00(15) ?
    O1 N2 C12 C7 . . . . -0.6(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N1 H1 O1 . 0.86 1.96 2.6280(18) 133.8
    C3 H3A O2 1_556 0.93 2.59 3.478(2) 159.2
