#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/40/2224057.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_2224057
loop_
_publ_author_name
'He, Chun-Lin'
'Du, Zhi-Ming'
'Tang, Zheng-Qiang'
'Cong, Xiao-Min'
'Meng, Ling-Qiao'
_publ_section_title
(5Z,7Z)-6,8-Dimethyl-9H-tetrazolo[1,5-b][1,2,4]triazepine
_journal_coeditor_code           WN2354
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2894
_journal_paper_doi               10.1107/S160053680904392X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C6 H8 N6'
_chemical_formula_moiety         'C6 H8 N6'
_chemical_formula_sum            'C6 H8 N6'
_chemical_formula_weight         164.18
_chemical_melting_point          477
_chemical_name_systematic
;
(5Z,7Z)-6,8-Dimethyl-9H-
tetrazolo[1,5-b][1,2,4]triazepine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 96.274(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.9184(8)
_cell_length_b                   13.584(3)
_cell_length_c                   13.767(3)
_cell_measurement_reflns_used    2263
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.33
_cell_volume                     728.4(3)
_computing_cell_refinement       'CrystalClear (Rigaku, 2008)'
_computing_data_collection       'CrystalClear (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear (Rigaku, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku Saturn 724+'
_diffrn_measurement_method       multi-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5029
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.33
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Chunk
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1647
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.031P)²+0.36P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0823
_reflns_number_gt                1445
_reflns_number_total             1647
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn2354.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224057
_cod_database_fobs_code          2224057
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.4467(3) 0.24707(7) 0.45448(7) 0.0165(2) Uani d . 1 . .
N N2 0.5870(3) 0.24983(8) 0.36816(7) 0.0208(2) Uani d . 1 . .
N N3 0.6547(3) 0.16030(8) 0.34635(8) 0.0223(3) Uani d . 1 . .
N N4 0.5650(3) 0.09674(8) 0.41698(7) 0.0195(2) Uani d . 1 . .
N N5 0.3238(3) 0.11503(8) 0.56546(8) 0.0207(3) Uani d . 1 . .
N N6 0.3868(3) 0.34046(7) 0.49433(7) 0.0176(2) Uani d . 1 . .
C C1 0.4389(3) 0.15238(9) 0.48318(8) 0.0163(3) Uani d . 1 . .
C C2 0.1660(3) 0.16746(9) 0.63408(8) 0.0165(3) Uani d . 1 . .
C C3 0.1175(3) 0.26544(9) 0.63462(9) 0.0180(3) Uani d . 1 . .
C C4 0.2395(3) 0.34313(9) 0.57359(9) 0.0165(3) Uani d . 1 . .
C C5 0.0598(3) 0.10241(9) 0.71313(9) 0.0202(3) Uani d . 1 . .
H H5A 0.2595 0.0819 0.7548 0.024 Uiso calc R 1 . .
H H5B -0.0569 0.0456 0.6844 0.024 Uiso calc R 1 . .
H H5C -0.0914 0.1380 0.7509 0.024 Uiso calc R 1 . .
C C6 0.1945(3) 0.44529(9) 0.61191(9) 0.0206(3) Uani d . 1 . .
H H6A 0.2920 0.4920 0.5705 0.025 Uiso calc R 1 . .
H H6B 0.3084 0.4503 0.6771 0.025 Uiso calc R 1 . .
H H6C -0.0457 0.4588 0.6126 0.025 Uiso calc R 1 . .
H H3 0.006(4) 0.2905(11) 0.6876(11) 0.025(4) Uiso d . 1 . .
H H5N 0.342(4) 0.0478(14) 0.5724(12) 0.036(5) Uiso 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 0.0214(5) 0.0138(5) 0.0148(5) 0.0006(4) 0.0043(4) 0.0002(4)
N2 0.0285(6) 0.0182(5) 0.0167(5) 0.0010(4) 0.0074(4) 0.0004(4)
N3 0.0309(6) 0.0180(5) 0.0191(5) 0.0013(5) 0.0078(4) 0.0014(4)
N4 0.0261(6) 0.0167(5) 0.0166(5) 0.0007(4) 0.0062(4) 0.0005(4)
N5 0.0315(6) 0.0130(5) 0.0193(5) 0.0016(4) 0.0106(5) 0.0019(4)
N6 0.0230(5) 0.0110(5) 0.0189(5) 0.0009(4) 0.0030(4) -0.0018(4)
C1 0.0177(6) 0.0151(6) 0.0161(6) 0.0000(5) 0.0013(4) 0.0005(4)
C2 0.0174(6) 0.0168(6) 0.0153(5) -0.0009(5) 0.0021(4) -0.0007(4)
C3 0.0196(6) 0.0181(6) 0.0168(6) 0.0000(5) 0.0050(5) -0.0007(5)
C4 0.0163(6) 0.0147(6) 0.0181(6) 0.0004(4) -0.0002(5) -0.0002(4)
C5 0.0240(6) 0.0174(6) 0.0202(6) -0.0003(5) 0.0072(5) 0.0024(5)
C6 0.0246(6) 0.0155(6) 0.0224(6) 0.0011(5) 0.0055(5) -0.0020(5)
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_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 N2 . . 107.83(10) ?
C1 N1 N6 . . 137.23(10) ?
N2 N1 N6 . . 114.45(9) ?
N3 N2 N1 . . 106.88(10) ?
N2 N3 N4 . . 110.69(10) ?
C1 N4 N3 . . 105.82(10) ?
C1 N5 C2 . . 126.17(11) ?
C1 N5 H5N . . 115.3(10) ?
C2 N5 H5N . . 118.4(10) ?
C4 N6 N1 . . 117.58(10) ?
N4 C1 N1 . . 108.78(10) ?
N4 C1 N5 . . 122.92(11) ?
N1 C1 N5 . . 128.29(11) ?
C3 C2 N5 . . 126.01(11) ?
C3 C2 C5 . . 122.01(11) ?
N5 C2 C5 . . 111.95(11) ?
C2 C3 C4 . . 131.03(12) ?
C2 C3 H3 . . 115.8(9) ?
C4 C3 H3 . . 112.8(9) ?
N6 C4 C3 . . 132.13(11) ?
N6 C4 C6 . . 113.82(10) ?
C3 C4 C6 . . 114.02(11) ?
C2 C5 H5A . . 109.5 ?
C2 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C2 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C4 C6 H6A . . 109.5 ?
C4 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C4 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
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 C1 . 1.3469(15) ?
N1 N2 . 1.3635(14) ?
N1 N6 . 1.4119(14) ?
N2 N3 . 1.2874(15) ?
N3 N4 . 1.3745(14) ?
N4 C1 . 1.3207(15) ?
N5 C1 . 1.3623(15) ?
N5 C2 . 1.3820(15) ?
N5 H5N . 0.920(18) ?
N6 C4 . 1.2897(16) ?
C2 C3 . 1.3446(17) ?
C2 C5 . 1.4958(16) ?
C3 C4 . 1.4615(17) ?
C3 H3 . 0.953(15) ?
C4 C6 . 1.5018(16) ?
C5 H5A . 0.9600 ?
C5 H5B . 0.9600 ?
C5 H5C . 0.9600 ?
C6 H6A . 0.9600 ?
C6 H6B . 0.9600 ?
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
N5 H5N N4 3_656 0.920(19) 1.999(19) 2.9156(17) 173.5(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
C1 N1 N2 N3 . . . . 0.80(13) ?
N6 N1 N2 N3 . . . . 174.17(10) ?
N1 N2 N3 N4 . . . . -0.47(14) ?
N2 N3 N4 C1 . . . . -0.04(14) ?
C1 N1 N6 C4 . . . . -12.5(2) ?
N2 N1 N6 C4 . . . . 176.81(10) ?
N3 N4 C1 N1 . . . . 0.55(13) ?
N3 N4 C1 N5 . . . . -179.54(11) ?
N2 N1 C1 N4 . . . . -0.84(14) ?
N6 N1 C1 N4 . . . . -171.93(13) ?
N2 N1 C1 N5 . . . . 179.24(12) ?
N6 N1 C1 N5 . . . . 8.2(2) ?
C2 N5 C1 N4 . . . . -174.90(12) ?
C2 N5 C1 N1 . . . . 5.0(2) ?
C1 N5 C2 C3 . . . . -4.3(2) ?
C1 N5 C2 C5 . . . . 177.67(12) ?
N5 C2 C3 C4 . . . . -7.1(2) ?
C5 C2 C3 C4 . . . . 170.75(12) ?
N1 N6 C4 C3 . . . . 0.64(19) ?
N1 N6 C4 C6 . . . . 178.52(10) ?
C2 C3 C4 N6 . . . . 10.9(2) ?
C2 C3 C4 C6 . . . . -167.02(13) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4808116
