#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/82/2218246.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_2218246
loop_
_publ_author_name
'Xing, Zheng'
'Han, Guang-Fan'
'Zhu, Wei-Feng'
'Zhao, Yu-Yuan'
_publ_section_title
;
 2-(1H-Tetrazol-5-yl)benzonitrile
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o816
_journal_paper_doi               10.1107/S1600536808008027
_journal_volume                  64
_journal_year                    2008
_chemical_formula_moiety         'C8 H5 N5'
_chemical_formula_sum            'C8 H5 N5'
_chemical_formula_weight         171.17
_chemical_name_common            2-(1H-tetrazol-5-yl)benzonitrile
_chemical_name_systematic        ?
_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                 95.27(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.9281(10)
_cell_length_b                   6.5420(13)
_cell_length_c                   24.867(5)
_cell_measurement_reflns_used    6584
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.78
_cell_measurement_theta_min      3.11
_cell_volume                     798.3(3)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            6844
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.22
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.2500
_exptl_crystal_size_mid          0.0700
_exptl_crystal_size_min          0.0700
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.241
_refine_ls_abs_structure_details none
_refine_ls_extinction_coef       0.044(14)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1553
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0549
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0619P)²+0.1285P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1375
_reflns_number_gt                1167
_reflns_number_total             1553
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2471.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2218246
_cod_database_fobs_code          2218246
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_refinement_flags
_atom_site_occupancy
C C1 0.5249(4) 0.5054(3) 0.13602(8) 0.0345(5) Uani d . 1
C C2 0.6569(4) 0.5277(3) 0.08892(8) 0.0403(5) Uani d . 1
C C3 0.6021(5) 0.6960(4) 0.05536(10) 0.0548(7) Uani d . 1
H H3 0.6925 0.7116 0.0244 0.066 Uiso calc R 1
C C4 0.4141(5) 0.8390(4) 0.06821(11) 0.0608(7) Uani d . 1
H H4 0.3762 0.9509 0.0457 0.073 Uiso calc R 1
C C5 0.2821(5) 0.8174(4) 0.11410(11) 0.0539(6) Uani d . 1
H H5 0.1537 0.9140 0.1223 0.065 Uiso calc R 1
C C6 0.3384(4) 0.6532(3) 0.14819(9) 0.0441(6) Uani d . 1
H H6 0.2504 0.6416 0.1796 0.053 Uiso calc R 1
C C7 0.5736(4) 0.3299(3) 0.17202(8) 0.0323(5) Uani d . 1
C C8 0.8482(5) 0.3773(4) 0.07280(9) 0.0476(6) Uani d . 1
N N1 0.9990(5) 0.2612(4) 0.05847(9) 0.0701(7) Uani d . 1
N N2 0.3814(3) 0.2405(3) 0.19806(7) 0.0399(5) Uani d . 1
N N3 0.4920(3) 0.0893(3) 0.22916(8) 0.0480(5) Uani d . 1
N N4 0.7498(3) 0.0881(3) 0.22217(7) 0.0458(5) Uani d . 1
N N5 0.8068(3) 0.2363(3) 0.18650(7) 0.0380(5) Uani d . 1
H H2 0.195(6) 0.253(4) 0.1939(10) 0.072(8) 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
C1 0.0263(10) 0.0405(11) 0.0363(11) 0.0019(9) 0.0016(8) 0.0010(9)
C2 0.0345(12) 0.0463(12) 0.0407(12) 0.0040(10) 0.0062(9) 0.0018(10)
C3 0.0598(16) 0.0595(15) 0.0473(14) 0.0110(12) 0.0171(12) 0.0137(12)
C4 0.0658(17) 0.0558(15) 0.0611(17) 0.0139(13) 0.0072(14) 0.0187(13)
C5 0.0491(14) 0.0480(14) 0.0642(16) 0.0144(11) 0.0041(12) -0.0003(12)
C6 0.0397(12) 0.0507(13) 0.0425(13) 0.0070(10) 0.0069(10) -0.0014(10)
C7 0.0221(9) 0.0434(11) 0.0319(11) 0.0004(8) 0.0055(8) -0.0021(9)
C8 0.0476(13) 0.0573(15) 0.0395(13) 0.0069(12) 0.0127(10) 0.0069(11)
N1 0.0705(15) 0.0809(15) 0.0623(15) 0.0288(13) 0.0242(12) 0.0062(12)
N2 0.0203(9) 0.0531(11) 0.0468(11) 0.0024(8) 0.0058(8) 0.0107(8)
N3 0.0306(9) 0.0600(12) 0.0540(12) 0.0029(9) 0.0074(8) 0.0166(10)
N4 0.0296(9) 0.0583(12) 0.0494(11) 0.0047(8) 0.0042(8) 0.0139(9)
N5 0.0238(8) 0.0510(10) 0.0400(10) 0.0035(8) 0.0065(7) 0.0070(8)
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
C6 C1 C2 118.61(19)
C6 C1 C7 119.24(18)
C2 C1 C7 122.13(17)
C3 C2 C1 120.31(19)
C3 C2 C8 117.86(19)
C1 C2 C8 121.81(19)
C4 C3 C2 119.7(2)
C4 C3 H3 120.1
C2 C3 H3 120.1
C5 C4 C3 120.3(2)
C5 C4 H4 119.9
C3 C4 H4 119.9
C4 C5 C6 120.5(2)
C4 C5 H5 119.8
C6 C5 H5 119.8
C5 C6 C1 120.5(2)
C5 C6 H6 119.7
C1 C6 H6 119.7
N5 C7 N2 107.65(17)
N5 C7 C1 128.31(17)
N2 C7 C1 123.99(17)
N1 C8 C2 177.8(2)
C7 N2 N3 109.61(16)
C7 N2 H2 130.9(16)
N3 N2 H2 118.7(16)
N4 N3 N2 106.16(16)
N3 N4 N5 110.25(16)
C7 N5 N4 106.33(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.386(3)
C1 C2 1.399(3)
C1 C7 1.462(3)
C2 C3 1.393(3)
C2 C8 1.445(3)
C3 C4 1.375(3)
C3 H3 0.9300
C4 C5 1.372(3)
C4 H4 0.9300
C5 C6 1.381(3)
C5 H5 0.9300
C6 H6 0.9300
C7 N5 1.323(2)
C7 N2 1.331(2)
C8 N1 1.142(3)
N2 N3 1.340(2)
N2 H2 0.92(3)
N3 N4 1.298(2)
N4 N5 1.361(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
N2 H2 N5 1_455 0.92(3) 1.91(3) 2.820(2) 172(2)
N2 H2 N4 1_455 0.92(3) 2.60(3) 3.374(2) 142(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
C6 C1 C2 C3 0.4(3)
C7 C1 C2 C3 179.22(19)
C6 C1 C2 C8 -178.3(2)
C7 C1 C2 C8 0.5(3)
C1 C2 C3 C4 -1.1(4)
C8 C2 C3 C4 177.7(2)
C2 C3 C4 C5 0.5(4)
C3 C4 C5 C6 0.7(4)
C4 C5 C6 C1 -1.3(4)
C2 C1 C6 C5 0.8(3)
C7 C1 C6 C5 -178.05(19)
C6 C1 C7 N5 -141.7(2)
C2 C1 C7 N5 39.5(3)
C6 C1 C7 N2 35.6(3)
C2 C1 C7 N2 -143.2(2)
N5 C7 N2 N3 -0.1(2)
C1 C7 N2 N3 -177.85(18)
C7 N2 N3 N4 0.3(2)
N2 N3 N4 N5 -0.4(2)
N2 C7 N5 N4 -0.2(2)
C1 C7 N5 N4 177.48(19)
N3 N4 N5 C7 0.4(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9868695
