#------------------------------------------------------------------------------
#$Date: 2015-06-20 04:56:12 +0300 (Sat, 20 Jun 2015) $
#$Revision: 139443 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/08/2240849.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_2240849
loop_
_publ_author_name
'Parrish, Damon A.'
'Kramer, Stephanie'
'Windler, G. Kenneth'
'Chavez, David E.'
'Leonard, Philip W.'
_publ_section_title
;
 Crystal structure of 2-diazoimidazole-4,5-dicarbonitrile
;
_journal_coeditor_code           CQ2016
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o491
_journal_paper_doi               10.1107/S2056989015010944
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C5 N6'
_chemical_formula_moiety         'C5 N6'
_chemical_formula_sum            'C5 N6'
_chemical_formula_weight         144.11
_chemical_melting_point          '413 K (expl.)'
_chemical_name_common
;
2-Diazo-4,5-dicyanoimidazole
;
_chemical_name_systematic
;
2-Diazoimidazole-4,5-dicarbonitrile
;
_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_Hall           'P 32 2"'
_space_group_name_H-M_alt        'P 32 2 1'
_symmetry_space_group_name_Hall  'P 32 2"'
_symmetry_space_group_name_H-M   'P 32 2 1'
_audit_creation_method
'from SHELXTL CIF, local template and enCIFer'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   8.0746(3)
_cell_length_b                   8.0746(3)
_cell_length_c                   16.7315(6)
_cell_measurement_temperature    150(2)
_cell_volume                     944.73(6)
_computing_cell_refinement
;
APEX2 and SAINT (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009) and XPREP (Bruker, 2008)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
CHEMDRAW Ultra (Cambridge Soft, 2014)
;
_computing_structure_refinement
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXTL (Sheldrick, 2008)
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9178
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.353
_diffrn_reflns_theta_min         3.157
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_correction_T_min  0.9300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0213
_refine_ls_R_factor_gt           0.0210
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0333P)²+0.1041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0574
_refine_ls_wR_factor_ref         0.0578
_reflns_number_gt                1269
_reflns_number_total             1289
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cq2016sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        944.73(8)
_cod_database_code               2240849
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'y, x, -z'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'
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 0.61645(16) 0.00825(16) 0.93835(6) 0.0254(3) Uani d 1
C C2 0.7396(2) 0.16549(19) 0.89882(7) 0.0226(3) Uani d 1
N N3 0.91448(16) 0.28157(17) 0.92732(6) 0.0239(3) Uani d 1
C C4 0.90565(19) 0.18858(19) 0.99570(7) 0.0225(3) Uani d 1
C C5 0.72502(19) 0.02197(19) 1.00215(7) 0.0240(3) Uani d 1
N N6 0.68567(16) 0.20682(16) 0.82574(6) 0.0238(3) Uani d 1
N N7 0.6461(2) 0.23873(19) 0.76756(7) 0.0329(3) Uani d 1
C C8 1.0629(2) 0.2582(2) 1.05016(7) 0.0258(3) Uani d 1
N N9 1.18839(19) 0.3094(2) 1.09341(7) 0.0351(3) Uani d 1
C C10 0.6572(2) -0.1202(2) 1.06366(8) 0.0299(3) Uani d 1
N N11 0.6055(2) -0.2345(2) 1.11254(8) 0.0441(4) 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
C2 N1 C5 99.75(11)
N3 C2 N1 121.08(11)
N3 C2 N6 119.59(12)
N1 C2 N6 119.33(12)
C2 N3 C4 99.74(11)
N3 C4 C5 109.70(11)
N3 C4 C8 122.12(13)
C5 C4 C8 128.18(12)
N1 C5 C4 109.72(11)
N1 C5 C10 122.03(12)
C4 C5 C10 128.23(12)
N7 N6 C2 178.50(12)
N9 C8 C4 178.23(16)
N11 C10 C5 178.82(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.3327(18)
N1 C5 1.3502(16)
C2 N3 1.3325(18)
C2 N6 1.3936(15)
N3 C4 1.3507(17)
C4 C5 1.4094(18)
C4 C8 1.4297(18)
C5 C10 1.4314(18)
N6 N7 1.0946(15)
C8 N9 1.1415(19)
C10 N11 1.144(2)
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
C5 N1 C2 N3 -0.01(16)
C5 N1 C2 N6 178.72(11)
N1 C2 N3 C4 -0.34(16)
N6 C2 N3 C4 -179.07(11)
C2 N3 C4 C5 0.53(14)
C2 N3 C4 C8 -179.64(12)
C2 N1 C5 C4 0.36(14)
C2 N1 C5 C10 -178.37(13)
N3 C4 C5 N1 -0.61(16)
C8 C4 C5 N1 179.57(12)
N3 C4 C5 C10 178.02(13)
C8 C4 C5 C10 -1.8(2)

_cod_database_fobs_code 2240849
