##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
<i>N</i>-[4-(Dimethylamino)benzylidene]-4<i>H</i>-1,2,4-triazol-4-amine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H13 N5'
_chemical_formula_sum     'C11 H13 N5'
_chemical_formula_iupac     'C11 H13 N5'
_chemical_formula_weight     215.26
_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     10.3665(16)
_cell_length_b     11.1585(19)
_cell_length_c     9.5248(12)
_cell_angle_alpha     90.00
_cell_angle_beta     90.2570(10)
_cell_angle_gamma     90.00
_cell_volume     1101.8(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1214
_cell_measurement_theta_min     2.682
_cell_measurement_theta_max     22.957
_cell_measurement_temperature     298(2)
_exptl_crystal_description     Cuboid
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.52
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.11
_exptl_crystal_density_diffrn     1.298
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     456
_exptl_absorpt_coefficient_mu     0.084
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2002)'
_exptl_absorpt_correction_T_min     0.9574
_exptl_absorpt_correction_T_max     0.9908
_exptl_special_details     ?
_diffrn_ambient_temperature     298(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     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5465
_diffrn_reflns_av_R_equivalents     0.0621
_diffrn_reflns_av_sigmaI/netI     0.0635
_diffrn_reflns_theta_min     1.96
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     1940
_reflns_number_gt     1184
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0791
_refine_ls_R_factor_gt     0.0474
_refine_ls_wR_factor_gt     0.1078
_refine_ls_wR_factor_ref     0.1186
_refine_ls_goodness_of_fit_ref     1.004
_refine_ls_restrained_S_all     1.004
_refine_ls_number_reflns     1940
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0462P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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     0.165
_refine_diff_density_min     -0.179
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.086(5)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
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'
_computing_data_collection     'SMART (Bruker, 2002)'
_computing_cell_refinement     'SAINT (Bruker, 2002)'
_computing_data_reduction     'SAINT (Bruker, 2002)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.20167(17) 0.23656(19) 0.4358(2) 0.0665(6) Uani d . 1 1 . .
    N N2 0.24339(17) 0.13578(17) 0.36475(19) 0.0599(5) Uani d . 1 1 . .
    N N3 0.34969(14) 0.14765(14) 0.56204(17) 0.0461(4) Uani d . 1 1 . .
    N N4 0.43764(14) 0.11434(15) 0.66817(17) 0.0498(5) Uani d . 1 1 . .
    N N5 0.87803(15) 0.16192(15) 1.14369(18) 0.0590(5) Uani d . 1 1 . .
    C C1 0.33047(19) 0.08539(19) 0.4428(2) 0.0540(6) Uani d . 1 1 . .
    H H1 0.3740 0.0154 0.4195 0.065 Uiso calc R 1 1 . .
    C C2 0.26690(19) 0.2406(2) 0.5530(2) 0.0588(6) Uani d . 1 1 . .
    H H2 0.2576 0.2996 0.6212 0.071 Uiso calc R 1 1 . .
    C C3 0.49452(17) 0.20274(18) 0.7270(2) 0.0469(5) Uani d . 1 1 . .
    H H3 0.4751 0.2797 0.6959 0.056 Uiso calc R 1 1 . .
    C C4 0.58726(17) 0.18934(17) 0.8392(2) 0.0437(5) Uani d . 1 1 . .
    C C5 0.61841(19) 0.07978(19) 0.8997(2) 0.0539(6) Uani d . 1 1 . .
    H H5 0.5744 0.0114 0.8707 0.065 Uiso calc R 1 1 . .
    C C6 0.7122(2) 0.06956(19) 1.0008(2) 0.0581(6) Uani d . 1 1 . .
    H H6 0.7301 -0.0051 1.0396 0.070 Uiso calc R 1 1 . .
    C C7 0.78200(17) 0.17091(18) 1.0468(2) 0.0458(5) Uani d . 1 1 . .
    C C8 0.74731(17) 0.28123(18) 0.9884(2) 0.0491(6) Uani d . 1 1 . .
    H H8 0.7890 0.3504 1.0186 0.059 Uiso calc R 1 1 . .
    C C9 0.65320(18) 0.28964(18) 0.8876(2) 0.0477(6) Uani d . 1 1 . .
    H H9 0.6329 0.3644 0.8505 0.057 Uiso calc R 1 1 . .
    C C10 0.9193(3) 0.0473(2) 1.1988(3) 0.0853(9) Uani d . 1 1 . .
    H H10A 0.8525 0.0144 1.2566 0.128 Uiso calc R 1 1 . .
    H H10B 0.9963 0.0579 1.2539 0.128 Uiso calc R 1 1 . .
    H H10C 0.9366 -0.0064 1.1224 0.128 Uiso calc R 1 1 . .
    C C11 0.9429(2) 0.2687(2) 1.1945(2) 0.0691(7) Uani d . 1 1 . .
    H H11A 0.9861 0.3074 1.1180 0.104 Uiso calc R 1 1 . .
    H H11B 1.0049 0.2468 1.2652 0.104 Uiso calc R 1 1 . .
    H H11C 0.8806 0.3225 1.2340 0.104 Uiso calc R 1 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
    N1 0.0658(12) 0.0829(14) 0.0507(13) 0.0148(10) -0.0210(10) -0.0039(11)
    N2 0.0641(11) 0.0706(13) 0.0448(12) -0.0003(10) -0.0169(9) 0.0003(10)
    N3 0.0464(9) 0.0559(11) 0.0359(10) -0.0001(8) -0.0119(8) 0.0019(9)
    N4 0.0521(10) 0.0569(11) 0.0403(11) 0.0002(8) -0.0165(8) 0.0024(9)
    N5 0.0578(10) 0.0678(13) 0.0512(12) 0.0076(10) -0.0251(9) -0.0019(10)
    C1 0.0651(13) 0.0536(13) 0.0432(14) -0.0038(11) -0.0132(11) -0.0005(11)
    C2 0.0547(13) 0.0712(16) 0.0503(15) 0.0103(12) -0.0140(11) -0.0079(12)
    C3 0.0441(11) 0.0530(13) 0.0436(14) 0.0054(10) -0.0059(10) -0.0006(11)
    C4 0.0454(11) 0.0481(12) 0.0374(13) 0.0048(9) -0.0075(9) -0.0018(10)
    C5 0.0642(13) 0.0516(13) 0.0456(14) -0.0066(10) -0.0164(11) -0.0038(11)
    C6 0.0744(14) 0.0508(13) 0.0488(14) 0.0075(11) -0.0204(12) 0.0025(11)
    C7 0.0472(11) 0.0536(13) 0.0364(13) 0.0077(10) -0.0068(9) -0.0039(10)
    C8 0.0462(11) 0.0535(13) 0.0475(14) -0.0016(10) -0.0104(10) -0.0063(11)
    C9 0.0489(11) 0.0493(13) 0.0448(14) 0.0051(9) -0.0099(10) -0.0002(10)
    C10 0.0898(17) 0.089(2) 0.0766(19) 0.0287(15) -0.0392(15) 0.0001(16)
    C11 0.0548(13) 0.0922(18) 0.0602(17) -0.0066(12) -0.0212(12) -0.0041(14)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    N1 C2 . 1.303(3) ?
    N1 N2 . 1.383(2) ?
    N2 C1 . 1.295(2) ?
    N3 C1 . 1.346(2) ?
    N3 C2 . 1.349(2) ?
    N3 N4 . 1.408(2) ?
    N4 C3 . 1.277(2) ?
    N5 C7 . 1.358(2) ?
    N5 C10 . 1.446(3) ?
    N5 C11 . 1.450(3) ?
    C1 H1 . 0.9300 ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.442(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.389(3) ?
    C4 C9 . 1.389(3) ?
    C5 C6 . 1.370(3) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.411(3) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.397(3) ?
    C8 C9 . 1.369(3) ?
    C8 H8 . 0.9300 ?
    C9 H9 . 0.9300 ?
    C10 H10A . 0.9600 ?
    C10 H10B . 0.9600 ?
    C10 H10C . 0.9600 ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
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
    C2 N1 N2 . . 106.54(17) ?
    C1 N2 N1 . . 106.92(17) ?
    C1 N3 C2 . . 104.55(17) ?
    C1 N3 N4 . . 124.23(17) ?
    C2 N3 N4 . . 131.21(17) ?
    C3 N4 N3 . . 114.03(17) ?
    C7 N5 C10 . . 121.78(18) ?
    C7 N5 C11 . . 120.24(17) ?
    C10 N5 C11 . . 117.98(18) ?
    N2 C1 N3 . . 111.1(2) ?
    N2 C1 H1 . . 124.4 ?
    N3 C1 H1 . . 124.4 ?
    N1 C2 N3 . . 110.9(2) ?
    N1 C2 H2 . . 124.6 ?
    N3 C2 H2 . . 124.6 ?
    N4 C3 C4 . . 123.37(19) ?
    N4 C3 H3 . . 118.3 ?
    C4 C3 H3 . . 118.3 ?
    C5 C4 C9 . . 117.30(18) ?
    C5 C4 C3 . . 123.47(18) ?
    C9 C4 C3 . . 119.19(18) ?
    C6 C5 C4 . . 121.84(19) ?
    C6 C5 H5 . . 119.1 ?
    C4 C5 H5 . . 119.1 ?
    C5 C6 C7 . . 120.83(19) ?
    C5 C6 H6 . . 119.6 ?
    C7 C6 H6 . . 119.6 ?
    N5 C7 C8 . . 121.48(18) ?
    N5 C7 C6 . . 121.64(18) ?
    C8 C7 C6 . . 116.88(18) ?
    C9 C8 C7 . . 121.39(19) ?
    C9 C8 H8 . . 119.3 ?
    C7 C8 H8 . . 119.3 ?
    C8 C9 C4 . . 121.70(19) ?
    C8 C9 H9 . . 119.1 ?
    C4 C9 H9 . . 119.1 ?
    N5 C10 H10A . . 109.5 ?
    N5 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    N5 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    N5 C11 H11A . . 109.5 ?
    N5 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    N5 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
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
    C2 N1 N2 C1 . . . . 0.1(2) ?
    C1 N3 N4 C3 . . . . 143.42(19) ?
    C2 N3 N4 C3 . . . . -38.0(3) ?
    N1 N2 C1 N3 . . . . -0.3(2) ?
    C2 N3 C1 N2 . . . . 0.5(2) ?
    N4 N3 C1 N2 . . . . 179.38(16) ?
    N2 N1 C2 N3 . . . . 0.2(2) ?
    C1 N3 C2 N1 . . . . -0.4(2) ?
    N4 N3 C2 N1 . . . . -179.24(17) ?
    N3 N4 C3 C4 . . . . 179.31(16) ?
    N4 C3 C4 C5 . . . . -3.8(3) ?
    N4 C3 C4 C9 . . . . 173.89(18) ?
    C9 C4 C5 C6 . . . . -1.4(3) ?
    C3 C4 C5 C6 . . . . 176.31(19) ?
    C4 C5 C6 C7 . . . . -0.5(3) ?
    C10 N5 C7 C8 . . . . -176.5(2) ?
    C11 N5 C7 C8 . . . . 3.2(3) ?
    C10 N5 C7 C6 . . . . 3.8(3) ?
    C11 N5 C7 C6 . . . . -176.49(19) ?
    C5 C6 C7 N5 . . . . -177.92(19) ?
    C5 C6 C7 C8 . . . . 2.4(3) ?
    N5 C7 C8 C9 . . . . 177.99(18) ?
    C6 C7 C8 C9 . . . . -2.3(3) ?
    C7 C8 C9 C4 . . . . 0.4(3) ?
    C5 C4 C9 C8 . . . . 1.5(3) ?
    C3 C4 C9 C8 . . . . -176.33(18) ?
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
    _geom_hbond_publ_flag
    C1 H1 N4 3_656 0.93 2.57 3.448(3) 157 yes
    C2 H2 N2 4_566 0.93 2.43 3.284(3) 152 yes
    C11 H11B N1 1_656 0.96 2.60 3.543(3) 166 yes
data_global
_journal_date_recd_electronic     2012-04-01
_journal_date_accepted     2012-04-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      5
_journal_page_first     o1343
_journal_page_last     o1343
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812014511
_journal_coeditor_code     FF2062
_publ_contact_author_name     'Zhou, Hui-Liang'
_publ_contact_author_address
;
     College of Chemistry and Chemical Engineering
     Ningxia University
     Yinchuan 750021
     Ninxia
     People's Republic of China
;
_publ_contact_author_email     zhouhl@nxu.edu.cn
_publ_contact_author_fax     '86 0951 2062413'
_publ_contact_author_phone     '86 0951 2062413'
_publ_section_title
;
<i>N</i>-[4-(Dimethylamino)benzylidene]-4<i>H</i>-1,2,4-triazol-4-amine
;
loop_
    _publ_author_name
    _publ_author_address
    'Zhou, Hui-Liang'
;
College of Chemistry and Chemical Engineering
Ningxia University
Yinchuan 750021
Ninxia
People's Republic of China
;
    'Zhang, Xiao-Min'
;
College of Chemistry and Chemical Engineering
Ningxia University
Yinchuan 750021
Ninxia
People's Republic of China
;