##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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/  #
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# This file may be used for bona fide research purposes within the           #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2009-06-25
_journal_date_accepted     2009-06-29
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      8
_journal_page_first     o1760
_journal_page_last     o1760
_journal_paper_category     QO
_journal_coeditor_code     XU2546
_publ_contact_author_name     'Du, Zhi Ming'
_publ_contact_author_address
;
State Key Laboratory of Explosion Science and Technology
Beijing Institute of Technology
Beijing 100081
People's Republic of China
;
_publ_contact_author_email     'duzhiming430@sohu.com'
_publ_contact_author_fax     '86-10-68912765'
_publ_contact_author_phone     '86-10-68912765'
_publ_section_title
;
1-Isopropylideneamino-1H-tetrazol-5-amine
;
loop_
    _publ_author_name
    _publ_author_address
    'He, Chun-Lin'
;
State Key Laboratory of Explosion Science and Technology
Beijing Institute of Technology
Beijing 100081
People's Republic of China
;
    'Du, Zhi-Ming'
;
State Key Laboratory of Explosion Science and Technology
Beijing Institute of Technology
Beijing 100081
People's Republic of China
;
    'Tang, Zheng-Qiang'
;
State Key Laboratory of Explosion Science and Technology
Beijing Institute of Technology
Beijing 100081
People's Republic of China
;
    'Cong, Xiao-Min'
;
State Key Laboratory of Explosion Science and Technology
Beijing Institute of Technology
Beijing 100081
People's Republic of China
;
    'Meng, Ling-Qiao'
;
State Key Laboratory of Explosion Science and Technology
Beijing Institute of Technology
Beijing 100081
People's Republic of China
;
data_I
_chemical_name_systematic
;
1-Isopropylideneamino-1H<ι>-tetrazol-5-amine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C4 H8 N6'
_chemical_formula_sum     'C4 H8 N6'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C4 H8 N6'
_chemical_formula_weight     140.16
_chemical_melting_point     445
_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     7.488(2)
_cell_length_b     7.4238(19)
_cell_length_c     11.997(3)
_cell_angle_alpha     90.00
_cell_angle_beta     97.145(3)
_cell_angle_gamma     90.00
_cell_volume     661.7(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2076
_cell_measurement_theta_min     3.05
_cell_measurement_theta_max     27.48
_cell_measurement_temperature     93(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     Colourless
_exptl_crystal_size_max     0.43
_exptl_crystal_size_mid     0.43
_exptl_crystal_size_min     0.33
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.407
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     296
_exptl_absorpt_coefficient_mu     0.102
_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     93(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Rotating Anode'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku Saturn724+'
_diffrn_measurement_method     multi-scan
_diffrn_detector_area_resol_mean     28.5714
_diffrn_reflns_number     5172
_diffrn_reflns_av_R_equivalents     0.0236
_diffrn_reflns_av_sigmaI/netI     0.0266
_diffrn_reflns_theta_min     3.23
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -8
_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     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_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     1520
_reflns_number_gt     1334
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0410
_refine_ls_R_factor_gt     0.0361
_refine_ls_wR_factor_gt     0.0837
_refine_ls_wR_factor_ref     0.0876
_refine_ls_goodness_of_fit_ref     0.997
_refine_ls_restrained_S_all     0.997
_refine_ls_number_reflns     1520
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
            'calc w=1/[σ²(Fo²)+(0.045P)²+0.16P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.281
_refine_diff_density_min     -0.173
_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     'CrystalClear (Rigaku, 2008)'
_computing_cell_refinement     'CrystalClear (Rigaku, 2008)'
_computing_data_reduction     'CrystalClear (Rigaku, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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
    N N1 0.90734(13) 0.19832(13) 0.44509(8) 0.0177(2) Uani d . 1 . .
    N N2 0.84796(13) 0.34792(13) 0.38501(8) 0.0182(2) Uani d . 1 . .
    N N3 0.78344(13) 0.46815(13) 0.44617(8) 0.0181(2) Uani d . 1 . .
    N N4 0.79984(12) 0.39605(12) 0.55284(7) 0.0144(2) Uani d . 1 . .
    N N5 0.74880(12) 0.46344(12) 0.65193(7) 0.0165(2) Uani d . 1 . .
    N N6 0.91309(15) 0.12338(14) 0.63884(8) 0.0223(2) Uani d . 1 . .
    C C1 0.87689(14) 0.23122(15) 0.55029(9) 0.0153(2) Uani d . 1 . .
    C C2 0.66745(14) 0.61599(15) 0.65364(9) 0.0169(2) Uani d . 1 . .
    C C3 0.61800(16) 0.74455(16) 0.55860(10) 0.0215(3) Uani d . 1 . .
    H H3A 0.7275 0.7992 0.5366 0.026 Uiso calc R 1 . .
    H H3B 0.5397 0.8391 0.5825 0.026 Uiso calc R 1 . .
    H H3C 0.5545 0.6795 0.4945 0.026 Uiso calc R 1 . .
    C C4 0.62021(16) 0.66948(17) 0.76627(10) 0.0232(3) Uani d . 1 . .
    H H4A 0.6608 0.5760 0.8213 0.028 Uiso calc R 1 . .
    H H4B 0.4895 0.6838 0.7624 0.028 Uiso calc R 1 . .
    H H4C 0.6794 0.7837 0.7891 0.028 Uiso calc R 1 . .
    H H6A 0.887(2) 0.156(2) 0.7063(14) 0.033(4) Uiso d . 1 . .
    H H6B 0.972(2) 0.025(2) 0.6261(13) 0.037(4) Uiso 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
    N1 0.0210(5) 0.0176(5) 0.0146(5) 0.0012(4) 0.0026(4) -0.0006(4)
    N2 0.0214(5) 0.0174(5) 0.0161(5) 0.0008(4) 0.0036(4) -0.0003(4)
    N3 0.0230(5) 0.0186(5) 0.0133(4) 0.0000(4) 0.0045(4) 0.0006(4)
    N4 0.0175(5) 0.0144(5) 0.0117(4) 0.0008(3) 0.0030(3) -0.0010(3)
    N5 0.0192(5) 0.0183(5) 0.0127(4) -0.0001(4) 0.0042(4) -0.0031(4)
    N6 0.0337(6) 0.0202(5) 0.0137(5) 0.0093(4) 0.0062(4) 0.0008(4)
    C1 0.0152(5) 0.0167(5) 0.0141(5) -0.0007(4) 0.0026(4) -0.0019(4)
    C2 0.0151(5) 0.0167(5) 0.0190(6) -0.0019(4) 0.0025(4) -0.0029(4)
    C3 0.0243(6) 0.0185(6) 0.0220(6) 0.0043(4) 0.0045(5) 0.0002(5)
    C4 0.0261(6) 0.0244(6) 0.0196(6) 0.0046(5) 0.0043(5) -0.0055(5)
_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 C1 . 1.3326(14) ?
    N1 N2 . 1.3678(13) ?
    N2 N3 . 1.2870(13) ?
    N3 N4 . 1.3784(13) ?
    N4 C1 . 1.3549(14) ?
    N4 N5 . 1.3866(12) ?
    N5 C2 . 1.2873(15) ?
    N6 C1 . 1.3309(14) ?
    N6 H6A . 0.891(17) ?
    N6 H6B . 0.878(17) ?
    C2 C4 . 1.4924(16) ?
    C2 C3 . 1.4977(16) ?
    C3 H3A . 0.9800 ?
    C3 H3B . 0.9800 ?
    C3 H3C . 0.9800 ?
    C4 H4A . 0.9800 ?
    C4 H4B . 0.9800 ?
    C4 H4C . 0.9800 ?
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
    C1 N1 N2 . . 105.52(9) ?
    N3 N2 N1 . . 112.53(9) ?
    N2 N3 N4 . . 105.28(9) ?
    C1 N4 N3 . . 108.59(9) ?
    C1 N4 N5 . . 120.58(9) ?
    N3 N4 N5 . . 130.82(9) ?
    C2 N5 N4 . . 120.83(9) ?
    C1 N6 H6A . . 121.1(10) ?
    C1 N6 H6B . . 114.8(10) ?
    H6A N6 H6B . . 123.9(14) ?
    N6 C1 N1 . . 127.15(11) ?
    N6 C1 N4 . . 124.77(10) ?
    N1 C1 N4 . . 108.08(9) ?
    N5 C2 C4 . . 114.48(10) ?
    N5 C2 C3 . . 128.40(10) ?
    C4 C2 C3 . . 117.11(10) ?
    C2 C3 H3A . . 109.5 ?
    C2 C3 H3B . . 109.5 ?
    H3A C3 H3B . . 109.5 ?
    C2 C3 H3C . . 109.5 ?
    H3A C3 H3C . . 109.5 ?
    H3B C3 H3C . . 109.5 ?
    C2 C4 H4A . . 109.5 ?
    C2 C4 H4B . . 109.5 ?
    H4A C4 H4B . . 109.5 ?
    C2 C4 H4C . . 109.5 ?
    H4A C4 H4C . . 109.5 ?
    H4B C4 H4C . . 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
    C1 N1 N2 N3 . . . . -0.23(12) ?
    N1 N2 N3 N4 . . . . -0.08(12) ?
    N2 N3 N4 C1 . . . . 0.37(11) ?
    N2 N3 N4 N5 . . . . -178.25(10) ?
    C1 N4 N5 C2 . . . . -176.51(10) ?
    N3 N4 N5 C2 . . . . 1.97(17) ?
    N2 N1 C1 N6 . . . . -179.99(11) ?
    N2 N1 C1 N4 . . . . 0.45(11) ?
    N3 N4 C1 N6 . . . . 179.91(10) ?
    N5 N4 C1 N6 . . . . -1.31(16) ?
    N3 N4 C1 N1 . . . . -0.52(12) ?
    N5 N4 C1 N1 . . . . 178.26(9) ?
    N4 N5 C2 C4 . . . . 179.59(9) ?
    N4 N5 C2 C3 . . . . -1.35(17) ?
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
    N6 H6A N2 4_566 0.890(16) 2.200(17) 3.0600(16) 162.6(13)
    N6 H6B N1 3_756 0.876(15) 2.118(15) 2.9770(16) 166.4(14)
