##############################################################################
#                                                                            #
# 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
_database_code_depnum_ccdc_archive 'CCDC 1468833'
_audit_creation_method     'SHELXL-2014/7'
_journal_date_recd_electronic     2016-03-02
_journal_date_accepted     2016-03-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2016
_journal_volume     72
_journal_issue      4
_journal_page_first     556
_journal_page_last     558
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989016004497
_journal_coeditor_code     BG2582
_publ_contact_author_name     'Gene-Hsiang Lee'
_publ_contact_author_address
;
Instrumentation Center
National Taiwan University
Taipei, Taiwan
;
_publ_contact_author_email     ghlee@ntu.edu.tw
_publ_contact_author_fax     '886-2-33668659'
_publ_contact_author_phone     '886-2-33662808'
_publ_section_title
;
Crystal structure of 1,2-bis[(1H-imidazol-2-yl)methylidene]hydrazine and
its one-dimensional hydrogen-bonding network
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Lee, Chia-Hwa' .
;
Department of Chemistry
National Taiwan University
Taipei, Taiwan
;
    'Lee, Gene-Hsiang' .
;
Instrumentation Center
National Taiwan University
Taipei, Taiwan
;
_publ_section_synopsis
;
In the title compound, two imidazolyl groups are separated by a zigzag
--CH=N---N=CH-- linkage. Each molecule forms four N---H...N
hydrogen bonds with two neighbouring molecules to constitute a one-dimensional
ladder-like structure along the a axis.
;
_chemical_name_systematic
;
1,2-Bis[(1H-imidazol-2-yl)methylidene]hydrazine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C8 H8 N6'
_chemical_formula_sum     'C8 H8 N6'
_chemical_formula_iupac     'C8 H8 N6'
_chemical_formula_weight     188.20
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/n'
_space_group_name_Hall     '-P 2yn'
loop_
    _space_group_symop_operation_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     5.0618(3)
_cell_length_b     14.6282(8)
_cell_length_c     6.1294(4)
_cell_angle_alpha     90
_cell_angle_beta     106.321(2)
_cell_angle_gamma     90
_cell_volume     435.56(5)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2074
_cell_measurement_theta_min     2.78
_cell_measurement_theta_max     27.49
_cell_measurement_temperature     150(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.350
_exptl_crystal_size_mid     0.100
_exptl_crystal_size_min     0.030
_exptl_crystal_density_diffrn     1.435
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     196
_exptl_absorpt_coefficient_mu     0.099
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_shelx_estimated_absorpt_T_min     0.966
_shelx_estimated_absorpt_T_max     0.997
_exptl_absorpt_correction_T_min     0.7023
_exptl_absorpt_correction_T_max     0.7456
_diffrn_ambient_temperature     150(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker D8 VENTURE'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     2614
_diffrn_reflns_av_R_equivalents     0.0142
_diffrn_reflns_theta_min     2.785
_diffrn_reflns_theta_max     27.495
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -7
_diffrn_reflns_limit_l_max     6
_refine_special_details     ?
_reflns_number_total     999
_reflns_number_gt     903
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0467
_refine_ls_R_factor_gt     0.0423
_refine_ls_wR_factor_gt     0.1133
_refine_ls_wR_factor_ref     0.1165
_refine_ls_goodness_of_fit_ref     1.119
_refine_ls_restrained_S_all     1.119
_refine_ls_number_reflns     999
_refine_ls_number_parameters     68
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0528P)²+0.2863P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.312
_refine_diff_density_min     -0.259
_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
;
APEX3 (Bruker, 2015)
;
_computing_cell_refinement
;
SAINT (Bruker, 2015)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 -0.1374(2) 0.62851(8) 0.4802(2) 0.0175(3) Uani d 1 . .
    H H1 0.055(5) 0.6193(14) 0.515(4) 0.037(6) Uiso d 1 . .
    C C2 -0.2801(3) 0.67725(10) 0.2944(2) 0.0204(4) Uani d 1 . .
    H H2 -0.2082 0.7044 0.1823 0.025 Uiso calc 1 . .
    C C3 -0.5481(3) 0.67920(10) 0.3022(2) 0.0197(3) Uani d 1 . .
    H H3 -0.6956 0.7084 0.1937 0.024 Uiso calc 1 . .
    N N4 -0.5714(2) 0.63279(8) 0.4899(2) 0.0187(3) Uani d 1 . .
    C C5 -0.3193(3) 0.60313(10) 0.5944(2) 0.0162(3) Uani d 1 . .
    C C6 -0.2539(3) 0.55035(10) 0.8020(2) 0.0180(3) Uani d 1 . .
    H H6 -0.3975 0.5336 0.8659 0.022 Uiso calc 1 . .
    N N7 -0.0068(3) 0.52574(8) 0.9014(2) 0.0195(3) Uani d 1 . .
_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
    N1 C5 . 1.3557(18) ?
    N1 C2 . 1.3656(18) ?
    N1 H1 . 0.95(2) ?
    C2 C3 . 1.371(2) ?
    C2 H2 . 0.9500 ?
    C3 N4 . 1.3689(19) ?
    C3 H3 . 0.9500 ?
    N4 C5 . 1.3295(18) ?
    C5 C6 . 1.445(2) ?
    C6 N7 . 1.2795(19) ?
    C6 H6 . 0.9500 ?
    N7 N7 3_567 1.409(2) ?
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
    C5 N1 C2 . . 107.26(12) ?
    C5 N1 H1 . . 130.4(13) ?
    C2 N1 H1 . . 122.3(13) ?
    N1 C2 C3 . . 106.15(12) ?
    N1 C2 H2 . . 126.9 ?
    C3 C2 H2 . . 126.9 ?
    N4 C3 C2 . . 109.81(13) ?
    N4 C3 H3 . . 125.1 ?
    C2 C3 H3 . . 125.1 ?
    C5 N4 C3 . . 105.60(12) ?
    N4 C5 N1 . . 111.18(13) ?
    N4 C5 C6 . . 123.37(13) ?
    N1 C5 C6 . . 125.46(13) ?
    N7 C6 C5 . . 121.43(13) ?
    N7 C6 H6 . . 119.3 ?
    C5 C6 H6 . . 119.3 ?
    C6 N7 N7 . 3_567 111.41(15) ?
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
    C5 N1 C2 C3 . . . . -0.35(16) ?
    N1 C2 C3 N4 . . . . 0.21(17) ?
    C2 C3 N4 C5 . . . . 0.02(17) ?
    C3 N4 C5 N1 . . . . -0.25(16) ?
    C3 N4 C5 C6 . . . . -179.93(13) ?
    C2 N1 C5 N4 . . . . 0.38(17) ?
    C2 N1 C5 C6 . . . . -179.95(14) ?
    N4 C5 C6 N7 . . . . -177.58(13) ?
    N1 C5 C6 N7 . . . . 2.8(2) ?
    C5 C6 N7 N7 . . . 3_567 -179.35(14) ?
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 N4 1_655 0.95(2) 1.95(2) 2.8493(17) 157.9(19)
