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###        Electronic paper (Acta Crystallographica Section E)             ###
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#                                                                            #
# 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/  #
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#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2005-09-20
_journal_date_accepted     2005-09-26
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue     10
_journal_page_first     o3485
_journal_page_last     o3486
_journal_paper_category     EO
_journal_coeditor_code     WN6382
_publ_contact_author_name     'Dr. Pengwu Zheng'
_publ_contact_author_address
;
School of Pharmacy,
Jiangxi Science and Technology Normal University,
Nanchang, 330013
People's Republic of China
;
_publ_contact_author_email     zhengpw@sohu.com
_publ_contact_author_fax     '86 0791-3805385'
_publ_contact_author_phone     '86 0791-3805385'
_publ_section_title
;
N,N'-Bis(3-nitrobenzylidene)hydrazine
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Zheng, Peng-Wu' .
;
School of Pharmacy
Jiangxi Science and Technology Normal University
Nanchang 330013
People's Republic of China
;
    'Wang, Wei' .
;
Department of Chemical Engineering
Anshan University of Science and Technology
Anshan 114002
People's Republic of China
;
    'Duan, Xue-Min' .
;
School of Pharmacy
Jiangxi Science and Technology Normal University
Nanchang 330013
People's Republic of China
;
data_I
_chemical_name_systematic
;
N,N'-Bis(3-nitrobenzylidene)hydrazine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H10 N4 O4'
_chemical_formula_sum     'C14 H10 N4 O4'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C14 H10 N4 O4'
_chemical_formula_weight     298.26
_chemical_melting_point        .469E-305
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     6.9694(19)
_cell_length_b     7.833(2)
_cell_length_c     12.990(4)
_cell_angle_alpha     90.00
_cell_angle_beta     105.175(4)
_cell_angle_gamma     90.00
_cell_volume     684.4(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1134
_cell_measurement_theta_min     3.04
_cell_measurement_theta_max     26.11
_cell_measurement_temperature     294(2)
_exptl_crystal_description     block
_exptl_crystal_colour     'light yellow'
_exptl_crystal_size_max     0.34
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.14
_exptl_crystal_density_diffrn     1.447
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     308
_exptl_absorpt_coefficient_mu     0.110
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.962
_exptl_absorpt_correction_T_max     1.000
_exptl_special_details
;
  ?
;
_diffrn_ambient_temperature     294(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3318
_diffrn_reflns_av_R_equivalents     0.0351
_diffrn_reflns_av_sigmaI/netI     0.0350
_diffrn_reflns_theta_min     3.04
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     9
_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_%     ?
_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     1204
_reflns_number_gt     814
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0641
_refine_ls_R_factor_gt     0.0381
_refine_ls_wR_factor_gt     0.0949
_refine_ls_wR_factor_ref     0.1158
_refine_ls_goodness_of_fit_ref     1.029
_refine_ls_restrained_S_all     1.029
_refine_ls_number_reflns     1204
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
      'calc w = 1/[σ²(Fo²)+(0.061P)²+0.0625P] 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     0.121
_refine_diff_density_min     -0.179
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.094(9)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-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'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 1997)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT (Bruker, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1997)'
_computing_publication_material     'SHELXTL'
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_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    O1 0.6567(2) 0.8906(2) 1.09525(13) 0.0816(5) Uani d . 1 . . O
    O2 0.8984(2) 0.7322(2) 1.17929(11) 0.0769(5) Uani d . 1 . . O
    N1 0.8070(2) 0.8074(2) 1.09941(14) 0.0562(5) Uani d . 1 . . N
    N2 1.4133(2) 0.53887(19) 1.00720(13) 0.0530(5) Uani d . 1 . . N
    C1 1.3163(3) 0.6158(2) 0.92344(15) 0.0504(5) Uani d . 1 . . C
    H1 1.3649 0.6158 0.8632 0.060 Uiso calc R 1 . . H
    C2 1.1288(2) 0.7046(2) 0.92005(14) 0.0461(5) Uani d . 1 . . C
    C3 1.0230(3) 0.7846(2) 0.82660(15) 0.0578(6) Uani d . 1 . . C
    H3 1.0708 0.7805 0.7662 0.069 Uiso calc R 1 . . H
    C4 0.8475(3) 0.8700(3) 0.82294(16) 0.0632(6) Uani d . 1 . . C
    H4 0.7788 0.9232 0.7601 0.076 Uiso calc R 1 . . H
    C5 0.7733(3) 0.8773(2) 0.91120(16) 0.0566(5) Uani d . 1 . . C
    H5 0.6550 0.9340 0.9090 0.068 Uiso calc R 1 . . H
    C6 0.8800(2) 0.7978(2) 1.00290(14) 0.0465(5) Uani d . 1 . . C
    C7 1.0551(2) 0.7121(2) 1.00964(13) 0.0458(5) Uani d . 1 . . C
    H7 1.1231 0.6599 1.0730 0.055 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
    O1 0.0668(10) 0.0918(12) 0.0978(12) 0.0211(9) 0.0419(8) -0.0015(9)
    O2 0.0742(10) 0.1063(12) 0.0551(9) 0.0186(9) 0.0256(8) 0.0065(9)
    N1 0.0505(10) 0.0588(11) 0.0645(11) -0.0021(8) 0.0239(8) -0.0091(8)
    N2 0.0480(9) 0.0547(10) 0.0627(10) 0.0028(7) 0.0259(8) 0.0010(8)
    C1 0.0525(11) 0.0496(11) 0.0551(11) -0.0037(9) 0.0250(9) -0.0024(9)
    C2 0.0472(10) 0.0450(10) 0.0486(10) -0.0051(8) 0.0171(8) -0.0033(8)
    C3 0.0608(12) 0.0684(13) 0.0459(11) -0.0046(10) 0.0170(9) -0.0034(9)
    C4 0.0570(12) 0.0738(14) 0.0519(12) 0.0032(11) 0.0021(10) 0.0028(10)
    C5 0.0428(10) 0.0584(12) 0.0649(13) 0.0020(9) 0.0074(9) -0.0053(10)
    C6 0.0430(10) 0.0460(10) 0.0516(11) -0.0055(8) 0.0143(8) -0.0049(8)
    C7 0.0456(11) 0.0445(10) 0.0487(11) -0.0012(8) 0.0146(8) 0.0014(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 N1 . 1.223(2) yes
    O2 N1 . 1.2181(19) yes
    N1 C6 . 1.473(2) yes
    N2 C1 . 1.272(2) yes
    N2 N2 3_867 1.409(3) yes
    C1 C2 . 1.471(2) ?
    C1 H1 . 0.9300 ?
    C2 C7 . 1.391(2) ?
    C2 C3 . 1.393(3) ?
    C3 C4 . 1.385(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.377(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.377(3) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.375(2) ?
    C7 H7 . 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
    O2 N1 O1 . . 123.11(17) yes
    O2 N1 C6 . . 118.68(16) yes
    O1 N1 C6 . . 118.20(17) yes
    C1 N2 N2 . 3_867 111.9(2) yes
    N2 C1 C2 . . 121.24(17) ?
    N2 C1 H1 . . 119.4 ?
    C2 C1 H1 . . 119.4 ?
    C7 C2 C3 . . 118.88(17) ?
    C7 C2 C1 . . 120.98(16) ?
    C3 C2 C1 . . 120.15(17) ?
    C4 C3 C2 . . 120.58(19) ?
    C4 C3 H3 . . 119.7 ?
    C2 C3 H3 . . 119.7 ?
    C5 C4 C3 . . 120.83(18) ?
    C5 C4 H4 . . 119.6 ?
    C3 C4 H4 . . 119.6 ?
    C4 C5 C6 . . 117.78(18) ?
    C4 C5 H5 . . 121.1 ?
    C6 C5 H5 . . 121.1 ?
    C7 C6 C5 . . 123.04(18) ?
    C7 C6 N1 . . 117.99(16) ?
    C5 C6 N1 . . 118.96(16) ?
    C6 C7 C2 . . 118.89(17) ?
    C6 C7 H7 . . 120.6 ?
    C2 C7 H7 . . 120.6 ?
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
    N2 N2 C1 C2 3_867 . . . 179.36(17) ?
    N2 C1 C2 C7 . . . . 2.2(3) ?
    N2 C1 C2 C3 . . . . -178.53(17) ?
    C7 C2 C3 C4 . . . . 0.0(3) ?
    C1 C2 C3 C4 . . . . -179.32(17) ?
    C2 C3 C4 C5 . . . . -0.3(3) ?
    C3 C4 C5 C6 . . . . 0.4(3) ?
    C4 C5 C6 C7 . . . . -0.2(3) ?
    C4 C5 C6 N1 . . . . 178.36(17) ?
    O2 N1 C6 C7 . . . . -3.7(2) ?
    O1 N1 C6 C7 . . . . 176.48(16) ?
    O2 N1 C6 C5 . . . . 177.64(16) ?
    O1 N1 C6 C5 . . . . -2.2(2) ?
    C5 C6 C7 C2 . . . . 0.0(3) ?
    N1 C6 C7 C2 . . . . -178.63(15) ?
    C3 C2 C7 C6 . . . . 0.1(2) ?
    C1 C2 C7 C6 . . . . 179.47(15) ?
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
    C5 H5 O1 3_677 0.93 2.56 3.487(3) 176 yes
