#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/09/2240986.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_2240986
loop_
_publ_author_name
'Windler, G. Kenneth'
'Scott, Brian L.'
'Tomson, Neil C.'
'Leonard, Philip W.'
_publ_section_title
;
 Crystal structure of 2-azido-1H-imidazole-4,5-dicarbonitrile
;
_journal_coeditor_code           ZS2337
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o633
_journal_paper_doi               10.1107/S2056989015013444
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C5 H N7'
_chemical_formula_moiety         'C5 H N7'
_chemical_formula_sum            'C5 H N7'
_chemical_formula_weight         159.13
_chemical_name_common            azidodicyanoimidazole
_chemical_name_systematic
;
2-Azido-1H-imidazole-4,5-dicarbonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.215(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3217(6)
_cell_length_b                   12.8128(11)
_cell_length_c                   7.5202(6)
_cell_measurement_reflns_used    2943
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      35.09
_cell_measurement_theta_min      3.18
_cell_volume                     689.51(10)
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_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
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100.0(10)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker D8 Quest with CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'Bruker Triumph curved graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13020
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         35.09
_diffrn_reflns_theta_min         3.18
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.9888
_exptl_absorpt_correction_T_min  0.9603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.249
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.556
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.556
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0562P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1172
_reflns_number_gt                2535
_reflns_number_total             2943
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            zs2337sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2240986
_cod_database_fobs_code          2240986
loop_
_symmetry_equiv_pos_as_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
_atom_site_symmetry_multiplicity
N N1 0.95971(8) 0.23656(4) 0.20204(8) 0.01244(12) Uani d 1 1
H H1 0.946(2) 0.2147(12) 0.087(3) 0.080 Uiso d 1 1
N N3 0.79681(9) -0.00660(5) 0.33122(9) 0.01989(14) Uani d 1 1
N N4 0.97866(9) 0.20303(5) 0.83076(8) 0.01915(14) Uani d 1 1
N N5 1.08587(9) 0.39994(5) 0.14988(8) 0.01601(13) Uani d 1 1
N N6 1.15492(9) 0.48197(5) 0.22731(9) 0.01800(14) Uani d 1 1
N N7 1.21954(11) 0.55869(5) 0.27860(11) 0.02869(17) Uani d 1 1
N N2 1.05744(8) 0.33629(4) 0.44841(8) 0.01346(13) Uani d 1 1
C C1 0.92901(9) 0.17977(5) 0.34810(8) 0.01148(13) Uani d 1 1
C C2 0.98919(9) 0.24295(5) 0.49778(8) 0.01203(13) Uani d 1 1
C C3 1.03672(9) 0.32810(5) 0.27026(9) 0.01232(13) Uani d 1 1
C C4 0.85397(9) 0.07743(5) 0.33564(9) 0.01397(13) Uani d 1 1
C C5 0.98406(9) 0.22016(5) 0.68201(9) 0.01401(14) Uani d 1 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
C3 N1 C1 106.32(5)
C3 N1 H1 126.2(11)
C1 N1 H1 127.1(10)
N6 N5 C3 112.74(6)
N7 N6 N5 172.47(8)
C3 N2 C2 103.55(5)
N1 C1 C2 105.25(6)
N1 C1 C4 124.29(6)
C2 C1 C4 130.45(6)
N2 C2 C1 111.15(6)
N2 C2 C5 121.75(6)
C1 C2 C5 127.10(6)
N2 C3 N1 113.73(6)
N2 C3 N5 128.17(6)
N1 C3 N5 118.09(6)
N3 C4 C1 177.65(7)
N4 C5 C2 179.07(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C3 1.3545(8)
N1 C1 1.3752(8)
N1 H1 0.893(19)
N3 C4 1.1530(8)
N4 C5 1.1489(9)
N5 N6 1.2549(8)
N5 C3 1.3907(8)
N6 N7 1.1232(9)
N2 C3 1.3202(8)
N2 C2 1.3770(9)
C1 C2 1.3808(9)
C1 C4 1.4171(9)
C2 C5 1.4241(9)
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
_geom_hbond_publ_flag
N1 H1 N4 1_554 0.89(2) 2.00(2) 2.8572(9) 160.9(14) yes
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
_geom_torsion_publ_flag
C3 N1 C1 C2 0.65(7) no
C3 N1 C1 C4 -178.28(6) no
C1 N1 C3 N2 -0.56(8) no
C1 N1 C3 N5 178.61(6) no
C3 N2 C2 C1 0.24(8) no
C3 N2 C2 C5 -179.26(6) no
C2 N2 C3 N1 0.20(8) no
C2 N2 C3 N5 -178.86(7) no
N6 N5 C3 N1 179.67(6) no
N6 N5 C3 N2 -1.31(11) no
N1 C1 C2 N2 -0.56(8) no
N1 C1 C2 C5 178.90(7) no
C4 C1 C2 N2 178.28(7) no
C4 C1 C2 C5 -2.26(12) no
