#------------------------------------------------------------------------------
#$Date: 2016-04-01 04:44:13 +0300 (Fri, 01 Apr 2016) $
#$Revision: 180670 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/16/2241627.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2241627
loop_
_publ_author_name
'Lee, Chia-Hwa'
'Lee, Gene-Hsiang'
_publ_section_title
;
 Crystal structure of
 1,2-bis[(1H-imidazol-2-yl)methylidene]hydrazine and its
 one-dimensional hydrogen-bonding network
;
_journal_coeditor_code           BG2582
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              556
_journal_page_last               558
_journal_paper_doi               10.1107/S2056989016004497
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C8 H8 N6'
_chemical_formula_moiety         'C8 H8 N6'
_chemical_formula_sum            'C8 H8 N6'
_chemical_formula_weight         188.20
_chemical_name_systematic
;
1,2-Bis[(1H-imidazol-2-yl)methylidene]hydrazine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.321(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.0618(3)
_cell_length_b                   14.6282(8)
_cell_length_c                   6.1294(4)
_cell_measurement_reflns_used    2074
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.78
_cell_volume                     435.56(5)
_computing_cell_refinement
;
SAINT (Bruker, 2015)
;
_computing_data_collection
;
APEX3 (Bruker, 2015)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0142
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2614
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         2.785
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       needle
_exptl_crystal_F_000             196
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.259
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     68
_refine_ls_number_reflns         999
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0528P)²+0.2863P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1165
_reflns_number_gt                903
_reflns_number_total             999
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bg2582sup1.cif
_cod_data_source_block           I
_cod_database_code               2241627
_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.
;
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.997
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'
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
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
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
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_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)
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_4
_geom_torsion
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)

_cod_database_fobs_code 2241627
