##############################################################################
#                                                                            #
# 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_global
_audit_creation_method     'from SHELXTL CIF, local template and enCIFer'
_journal_date_recd_electronic     2015-05-04
_journal_date_accepted     2015-06-05
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2015
_journal_volume     71
_journal_issue      7
_journal_page_first     o491
_journal_page_last     o491
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2056989015010944
_journal_coeditor_code     CQ2016
_publ_contact_author_name     'Dr. Philip W. Leonard'
_publ_contact_author_address
;
PO Box 1663 MS C920
Los Alamos National Laboratory
Los Alamos, NM 87545
USA
;
_publ_contact_author_email     'philipl@lanl.gov'
_publ_contact_author_fax     '505-667-0500'
_publ_contact_author_phone     '505-665-3637'
_publ_section_title
;
Crystal structure of 2-diazoimidazole-4,5-dicarbonitrile
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Parrish, Damon A.' ?
;
CBMSE, Code 6910
Naval Research Laboratory
Washington, DC 20375
USA
;
    'Kramer, Stephanie' ?
;
CBMSE, Code 6910
Naval Research Laboratory
Washington, DC 20375
USA
;
    'Windler, G. Kenneth' ?
;
PO Box 1663 MS C920
Los Alamos National Laboratory
Los Alamos, NM 87545
USA
;
    'Chavez, David E.' ?
;
PO Box 1663 MS C920
Los Alamos National Laboratory
Los Alamos, NM 87545
USA
;
    'Leonard, Philip W.' ?
;
PO Box 1663 MS C920
Los Alamos National Laboratory
Los Alamos, NM 87545
USA
;
data_I
_audit_creation_method     'from SHELXTL CIF, local template and enCIFer'
_database_code_depnum_ccdc_archive     'CCDC 1056377'
_chemical_name_systematic
;
2-Diazoimidazole-4,5-dicarbonitrile
;
_chemical_name_common
;
2-Diazo-4,5-dicyanoimidazole
;
_chemical_formula_moiety     'C5 N6'
_chemical_formula_sum     'C5 N6'
_chemical_formula_iupac     'C5 N6'
_chemical_formula_weight     144.11
_chemical_melting_point     '413 K (expl.)'
_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     trigonal
_space_group_name_H-M_alt     'P 32 2 1'
_space_group_name_Hall     'P 32 2"'
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'
_cell_length_a     8.0746(3)
_cell_length_b     8.0746(3)
_cell_length_c     16.7315(6)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     120
_cell_volume     944.73(8)
_cell_formula_units_Z     6
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min     ?
_cell_measurement_theta_max     ?
_cell_measurement_temperature     150(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     purple
_exptl_crystal_size_max     0.370
_exptl_crystal_size_mid     0.300
_exptl_crystal_size_min     0.080
_exptl_crystal_density_diffrn     1.520
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     432
_exptl_absorpt_coefficient_mu     0.111
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_absorpt_correction_T_min     0.9300
_exptl_absorpt_correction_T_max     0.9912
_diffrn_ambient_temperature     150(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine focus sealed tube'
_diffrn_measurement_device_type     'Bruker SMART APEXII CCD'
_diffrn_measurement_method     '\w scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9178
_diffrn_reflns_av_R_equivalents     0.0188
_diffrn_reflns_theta_min     3.157
_diffrn_reflns_theta_max     26.353
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     20
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     1289
_reflns_number_gt     1269
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0213
_refine_ls_R_factor_gt     0.0210
_refine_ls_wR_factor_gt     0.0574
_refine_ls_wR_factor_ref     0.0578
_refine_ls_goodness_of_fit_ref     1.086
_refine_ls_restrained_S_all     1.086
_refine_ls_number_reflns     1289
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     .
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[\s^2^(Fo^2^)+(0.0333P)^2^+0.1041P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     .
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.143
_refine_diff_density_min     -0.113
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
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
;
APEX2 (Bruker, 2009)
;
_computing_cell_refinement
;
APEX2 and SAINT (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009) and XPREP (Bruker, 2008)
;
_computing_structure_solution
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXTL (Sheldrick, 2008)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae <i>et al.</i>,
2008)
;
_computing_publication_material
;
<i>CHEMDRAW Ultra</i> (Cambridge Soft, 2014)
;
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 0.61645(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_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 0.0235(6) 0.0266(6) 0.0250(5) 0.0117(5) -0.0016(4) -0.0005(5)
    C2 0.0241(6) 0.0255(6) 0.0200(5) 0.0138(5) -0.0021(5) -0.0011(5)
    N3 0.0234(6) 0.0258(6) 0.0226(5) 0.0125(5) -0.0006(4) -0.0012(4)
    C4 0.0223(6) 0.0251(6) 0.0223(6) 0.0135(5) -0.0002(5) -0.0022(5)
    C5 0.0237(6) 0.0266(6) 0.0237(6) 0.0140(6) 0.0002(4) -0.0005(5)
    N6 0.0231(6) 0.0256(6) 0.0244(5) 0.0136(5) -0.0005(4) -0.0020(4)
    N7 0.0370(7) 0.0425(8) 0.0282(6) 0.0265(6) -0.0027(5) -0.0003(5)
    C8 0.0266(7) 0.0298(7) 0.0239(6) 0.0161(6) 0.0024(5) -0.0005(5)
    N9 0.0310(7) 0.0467(8) 0.0306(6) 0.0216(6) -0.0070(5) -0.0064(5)
    C10 0.0240(7) 0.0324(7) 0.0314(7) 0.0127(6) -0.0020(5) 0.0025(6)
    N11 0.0362(7) 0.0456(8) 0.0451(8) 0.0164(7) -0.0007(6) 0.0179(6)
_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 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_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
    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_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 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) ?
_iucr_refine_instructions_details
;
TITL chav078 in P3(2)21
CELL 0.71073   8.0746   8.0746  16.7315  90.000  90.000 120.000
ZERR    6.00   0.0003   0.0003   0.0006   0.000   0.000   0.000
LATT -1
SYMM -Y, X-Y, 0.66667+Z
SYMM -X+Y, -X, 0.33333+Z
SYMM Y, X, -Z
SYMM X-Y, -Y, 0.33333-Z
SYMM -X, -X+Y, 0.66667-Z
SFAC C H N
UNIT 30 0 36
TEMP -123.000
L.S. 8
BOND $H
ACTA
FMAP 2
MERG 2
PLAN 5
HTAB
SIZE 0.08 0.30 0.37
WPDB -2
CONF
WGHT    0.033300    0.104100
FVAR       0.29229
N1    3    0.616448    0.008253    0.938352    11.00000    0.02352    0.02657 =
         0.02499   -0.00053   -0.00158    0.01171
C2    1    0.739647    0.165487    0.898821    11.00000    0.02413    0.02554 =
         0.01999   -0.00110   -0.00215    0.01376
N3    3    0.914479    0.281573    0.927320    11.00000    0.02340    0.02581 =
         0.02260   -0.00121   -0.00062    0.01247
C4    1    0.905652    0.188579    0.995704    11.00000    0.02229    0.02513 =
         0.02226   -0.00219   -0.00022    0.01354
C5    1    0.725023    0.021973    1.002146    11.00000    0.02371    0.02658 =
         0.02373   -0.00048    0.00021    0.01403
N6    3    0.685667    0.206822    0.825740    11.00000    0.02314    0.02562 =
         0.02437   -0.00195   -0.00045    0.01356
N7    3    0.646124    0.238730    0.767563    11.00000    0.03697    0.04247 =
         0.02820   -0.00030   -0.00267    0.02654
C8    1    1.062864    0.258171    1.050157    11.00000    0.02659    0.02976 =
         0.02389   -0.00045    0.00237    0.01611
N9    3    1.188389    0.309402    1.093414    11.00000    0.03097    0.04670 =
         0.03063   -0.00637   -0.00705    0.02156
C10   1    0.657221   -0.120232    1.063659    11.00000    0.02405    0.03240 =
         0.03137    0.00248   -0.00202    0.01268
N11   3    0.605533   -0.234512    1.112542    11.00000    0.03623    0.04560 =
         0.04513    0.01793   -0.00074    0.01643
HKLF 4
REM  chav078 in P3(2)21
REM R1 =  0.0210 for    1269 Fo > 4sig(Fo)  and  0.0213 for all    1289 data
REM    100 parameters refined using      0 restraints
END
WGHT      0.0333      0.1041
REM No hydrogen bonds found for HTAB generation
REM Highest difference peak  0.143,  deepest hole -0.113,  1-sigma level  0.027
Q1    1   0.8110  0.1188  1.0093  11.00000  0.05    0.14
Q2    1   0.6935 -0.0170  0.9616  11.00000  0.05    0.11
Q3    1   0.6563  0.1124  0.9272  11.00000  0.05    0.10
Q4    1   0.5222 -0.0995  0.9148  11.00000  0.05    0.10
Q5    1   0.7147  0.1875  0.8648  11.00000  0.05    0.09
;