##############################################################################
###                                                                        ###
###        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_global
_audit_creation_method     ?
_journal_date_recd_electronic     2006-06-07
_journal_date_accepted     2006-06-28
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      8
_journal_page_first     o3209
_journal_page_last     o3210
_journal_paper_category     EO
_journal_coeditor_code     CV2070
_publ_contact_author_name     'PhD Anna V. Vologzhanina'
_publ_contact_author_address
;
Department of Chemistry
Samara State University
Samara
acad. Pavlov str., 1. 443011
Russia
;
_publ_contact_author_email     vologzhanina@mail.ru
_publ_contact_author_fax     '+7-8846-3345417'
_publ_contact_author_phone     '+7-8846-3345445'
_publ_section_title
;
1H-Benzimidazole-1-carbohydrazonamide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Sokolov, Andrey V.' ?
;
Department of Chemistry
Samara State University
acad. Pavlov str. 1
443011 Samara
Russian Federation
;
    'Vologzhanina, Anna V.' ?
;
Department of Chemistry
Samara State University
acad. Pavlov str. 1
443011 Samara
Russian Federation
;
    'Purygin, Petr P.' .
;
Department of Chemistry
Samara State University
acad. Pavlov str. 1
443011 Samara
Russian Federation
;
_exptl_special_details
;
Elemental analysis found: C, 54.82; H, 5.20. (C₈H₉N₅), requires: C,
54.85; H, 5.18 %. The ¹H NMR spectrum in DMSO-d₆ solution was recorded
on a Bruker WM-250 instrument working at 250.13 MHz and room temperature and
referred to extemal TMS. IR spectra were recorded on a Shimadzu FTIR-8400S.
¹H NMR (δ, ppm, DMSO-d₆): 7.94 d (1H, 4-H), 7.68 d (1H, 7-H), 7.28 m
(2H, 5,6-H), 8.42 s (1H, 2-H), 4.96 br s (N-NH₂), 6.24 br s (C-NH₂). IR
(KBr) νₘₐₓ/cm⁻¹ 3306 (s), 3124 (s), 1685 (s), 1674 (s), 1493 (s), 1462
(s), 1223 (s).
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1H-Benzimidazole-1-carbohydrazonamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C8 H9 N5'
_chemical_formula_sum     'C8 H9 N5'
_chemical_formula_iupac     'C8 H9 N5'
_chemical_formula_weight     175.20
_chemical_melting_point     436
_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     7.3890(15)
_cell_length_b     8.1520(16)
_cell_length_c     13.660(3)
_cell_angle_alpha     90.00
_cell_angle_beta     94.25(3)
_cell_angle_gamma     90.00
_cell_volume     820.5(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     24
_cell_measurement_theta_min     12
_cell_measurement_theta_max     14
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.60
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.418
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     368
_exptl_absorpt_coefficient_mu     0.095
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_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     'Siemens P3/PC'
_diffrn_measurement_method     ω/2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     1929
_diffrn_reflns_av_R_equivalents     0.0246
_diffrn_reflns_av_sigmaI/netI     0.0238
_diffrn_reflns_theta_min     2.99
_diffrn_reflns_theta_max     27.07
_diffrn_reflns_theta_full     27.07
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.992
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     0
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     0
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     2
_diffrn_standards_interval_count     98
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     2
_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 > 2sigma(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     1795
_reflns_number_gt     1448
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0591
_refine_ls_R_factor_gt     0.0464
_refine_ls_wR_factor_gt     0.1392
_refine_ls_wR_factor_ref     0.1430
_refine_ls_goodness_of_fit_ref     1.096
_refine_ls_restrained_S_all     1.096
_refine_ls_number_reflns     1795
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
           'calc w=1/[σ²(Fo²)+(0.0798P)²+0.29P] 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     0.011
_refine_ls_shift/su_mean     0.002
_refine_diff_density_max     0.348
_refine_diff_density_min     -0.207
_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'
_computing_data_collection     'P3/PC (Siemens, 1989)'
_computing_cell_refinement     'P3/PC'
_computing_data_reduction     'XDISK (Siemens, 1989)'
_computing_structure_solution     'SHELXTL (Sheldrick, 1998)'
_computing_structure_refinement     'SHELXTL'
_computing_molecular_graphics
                               'SHELXTL and TOPOS (Blatov et al.,  1999)'
_computing_publication_material     'SHELXTL'
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
    C C1 0.5500(2) 0.2281(2) 0.84344(12) 0.0312(4) Uani d . 1 . .
    H H1 0.5492 0.1155 0.8323 0.037 Uiso calc R 1 . .
    C C2 0.3657(3) 0.6150(2) 0.88709(14) 0.0389(4) Uani d . 1 . .
    H H2 0.2400 0.6127 0.8884 0.047 Uiso calc R 1 . .
    C C3 0.4624(3) 0.7586(2) 0.90254(15) 0.0439(5) Uani d . 1 . .
    H H3 0.4001 0.8548 0.9144 0.053 Uiso calc R 1 . .
    C C4 0.6499(3) 0.7638(2) 0.90088(14) 0.0403(4) Uani d . 1 . .
    H H4 0.7096 0.8634 0.9111 0.048 Uiso calc R 1 . .
    C C5 0.7503(2) 0.6246(2) 0.88436(13) 0.0345(4) Uani d . 1 . .
    H H5 0.8761 0.6275 0.8841 0.041 Uiso calc R 1 . .
    C C6 0.6522(2) 0.4800(2) 0.86810(11) 0.0273(4) Uani d . 1 . .
    C C7 0.4643(2) 0.4729(2) 0.86939(12) 0.0302(4) Uani d . 1 . .
    C C8 0.8842(2) 0.2563(2) 0.84960(11) 0.0266(4) Uani d . 1 . .
    N N1 0.70550(17) 0.31878(17) 0.85135(10) 0.0277(3) Uani d . 1 . .
    N N2 0.40322(19) 0.31221(19) 0.85282(11) 0.0342(4) Uani d . 1 . .
    N N3 1.09102(19) 0.05532(18) 0.88904(11) 0.0334(4) Uani d . 1 . .
    H H6 1.1870 0.1235 0.8905 0.040 Uiso d R 1 . .
    H H7 1.1114 -0.0137 0.9401 0.040 Uiso d R 1 . .
    N N4 0.91930(19) 0.12857(16) 0.90246(10) 0.0292(3) Uani d . 1 . .
    N N5 0.9939(2) 0.3400(2) 0.79285(12) 0.0405(4) Uani d . 1 . .
    H H8 1.1134 0.3179 0.7945 0.049 Uiso d R 1 . .
    H H9 0.9430 0.4070 0.7462 0.049 Uiso d R 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
    C1 0.0279(8) 0.0313(9) 0.0343(8) -0.0033(6) 0.0022(6) 0.0014(7)
    C2 0.0315(9) 0.0451(11) 0.0408(9) 0.0109(8) 0.0071(7) 0.0018(8)
    C3 0.0537(12) 0.0339(10) 0.0445(10) 0.0143(9) 0.0052(9) -0.0022(8)
    C4 0.0506(11) 0.0289(9) 0.0411(10) 0.0001(8) 0.0010(8) -0.0022(7)
    C5 0.0348(9) 0.0301(9) 0.0384(9) -0.0029(7) 0.0014(7) 0.0006(7)
    C6 0.0283(8) 0.0278(8) 0.0261(7) 0.0037(6) 0.0029(6) 0.0032(6)
    C7 0.0285(8) 0.0338(9) 0.0281(8) 0.0014(6) 0.0020(6) 0.0038(6)
    C8 0.0249(8) 0.0267(8) 0.0282(7) -0.0010(6) 0.0024(6) -0.0012(6)
    N1 0.0257(7) 0.0249(7) 0.0325(7) 0.0001(5) 0.0029(5) 0.0014(5)
    N2 0.0268(7) 0.0389(8) 0.0368(8) -0.0026(6) 0.0030(5) 0.0017(6)
    N3 0.0296(7) 0.0288(7) 0.0417(8) 0.0044(6) 0.0023(6) 0.0029(6)
    N4 0.0270(7) 0.0263(7) 0.0345(7) 0.0022(5) 0.0037(5) 0.0010(5)
    N5 0.0286(7) 0.0449(9) 0.0490(9) 0.0053(6) 0.0099(6) 0.0185(7)
_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
    C1 N2 . 1.297(2) no
    C1 N1 . 1.364(2) no
    C1 H1 . 0.9300 no
    C2 C3 . 1.380(3) no
    C2 C7 . 1.399(2) no
    C2 H2 . 0.9300 no
    C3 C4 . 1.388(3) no
    C3 H3 . 0.9300 no
    C4 C5 . 1.383(3) no
    C4 H4 . 0.9300 no
    C5 C6 . 1.394(2) no
    C5 H5 . 0.9300 no
    C6 C7 . 1.391(2) no
    C6 N1 . 1.395(2) no
    C7 N2 . 1.398(2) no
    C8 N4 . 1.282(2) no
    C8 N5 . 1.348(2) no
    C8 N1 . 1.417(2) no
    N3 N4 . 1.4264(19) no
    N3 H6 . 0.9000 no
    N3 H7 . 0.9000 no
    N5 H8 . 0.9000 no
    N5 H9 . 0.9000 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_3
    _geom_angle
    _geom_angle_publ_flag
    N2 C1 N1 . . 114.27(16) no
    N2 C1 H1 . . 122.9 no
    N1 C1 H1 . . 122.9 no
    C3 C2 C7 . . 117.28(17) no
    C3 C2 H2 . . 121.4 no
    C7 C2 H2 . . 121.4 no
    C2 C3 C4 . . 121.99(17) no
    C2 C3 H3 . . 119.0 no
    C4 C3 H3 . . 119.0 no
    C5 C4 C3 . . 121.74(18) no
    C5 C4 H4 . . 119.1 no
    C3 C4 H4 . . 119.1 no
    C4 C5 C6 . . 116.15(17) no
    C4 C5 H5 . . 121.9 no
    C6 C5 H5 . . 121.9 no
    C7 C6 N1 . . 104.92(14) no
    C7 C6 C5 . . 122.76(15) no
    N1 C6 C5 . . 132.29(15) no
    C6 C7 N2 . . 110.31(14) no
    C6 C7 C2 . . 120.08(16) no
    N2 C7 C2 . . 129.60(16) no
    N4 C8 N5 . . 129.02(16) no
    N4 C8 N1 . . 115.61(14) no
    N5 C8 N1 . . 115.36(14) no
    C1 N1 C6 . . 106.07(13) no
    C1 N1 C8 . . 125.74(14) no
    C6 N1 C8 . . 128.04(14) no
    C1 N2 C7 . . 104.42(14) no
    N4 N3 H6 . . 116.5 no
    N4 N3 H7 . . 105.2 no
    H6 N3 H7 . . 106.4 no
    C8 N4 N3 . . 114.35(13) no
    C8 N5 H8 . . 121.0 no
    C8 N5 H9 . . 118.5 no
    H8 N5 H9 . . 119.8 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
    C7 C2 C3 C4 . . . . 0.0(3) no
    C2 C3 C4 C5 . . . . -0.5(3) no
    C3 C4 C5 C6 . . . . 0.9(3) no
    C4 C5 C6 C7 . . . . -0.8(3) no
    C4 C5 C6 N1 . . . . -178.44(17) no
    N1 C6 C7 N2 . . . . -0.64(18) no
    C5 C6 C7 N2 . . . . -178.82(15) no
    N1 C6 C7 C2 . . . . 178.49(15) no
    C5 C6 C7 C2 . . . . 0.3(3) no
    C3 C2 C7 C6 . . . . 0.1(3) no
    C3 C2 C7 N2 . . . . 179.08(17) no
    N2 C1 N1 C6 . . . . 0.21(19) no
    N2 C1 N1 C8 . . . . 176.18(14) no
    C7 C6 N1 C1 . . . . 0.27(17) no
    C5 C6 N1 C1 . . . . 178.21(17) no
    C7 C6 N1 C8 . . . . -175.57(14) no
    C5 C6 N1 C8 . . . . 2.4(3) no
    N4 C8 N1 C1 . . . . -45.4(2) no
    N5 C8 N1 C1 . . . . 134.90(17) no
    N4 C8 N1 C6 . . . . 129.67(17) no
    N5 C8 N1 C6 . . . . -50.0(2) no
    N1 C1 N2 C7 . . . . -0.59(19) no
    C6 C7 N2 C1 . . . . 0.76(18) no
    C2 C7 N2 C1 . . . . -178.27(18) no
    N5 C8 N4 N3 . . . . -8.5(3) no
    N1 C8 N4 N3 . . . . 171.87(13) no
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
    N3 H6 N2 1_655 0.90 2.30 3.181(2) 165 y
    N3 H7 N4 3_757 0.90 2.37 3.224(2) 158 y
    N5 H9 N3 2_756 0.90 2.21 3.069(2) 160 y
    N5 H8 N2 1_655 0.90 2.23 3.083(2) 158 y
