#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/92/2229276.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_2229276
loop_
_publ_author_name
'Wang, Peng'
'Yue, Zheng'
'Zhang, Jie'
'Feng, Sheng-Yu'
_publ_section_title
;
 Bis[4-(2-isopropyl-2H-tetrazol-5-yl)phenyl]dimethylsilane
;
_journal_coeditor_code           XU5118
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o368
_journal_paper_doi               10.1107/S160053681100033X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C22 H28 N8 Si'
_chemical_formula_moiety         'C22 H28 N8 Si'
_chemical_formula_sum            'C22 H28 N8 Si'
_chemical_formula_weight         432.61
_chemical_name_systematic
;
Bis[4-(2-isopropyl-2H-tetrazol-5-yl)phenyl]dimethylsilane
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2722(14)
_cell_length_b                   11.536(2)
_cell_length_c                   28.444(6)
_cell_measurement_reflns_used    1662
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.545
_cell_measurement_theta_min      2.865
_cell_volume                     2386.2(8)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0492
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            12923
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.43
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_correction_T_min  0.9453
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.188
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2613
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.1230
_refine_ls_R_factor_gt           0.0875
_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)+(0.0693P)²+1.6746P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1897
_refine_ls_wR_factor_ref         0.2071
_reflns_number_gt                1827
_reflns_number_total             2613
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu5118.cif
_cod_data_source_block           I
_cod_database_code               2229276
_cod_database_fobs_code          2229276
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
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
Si Si1 0.0000 0.80602(11) 0.2500 0.0536(4) Uani d S 1 . .
N N1 0.5087(4) 0.4553(2) 0.40351(9) 0.0610(8) Uani d . 1 . .
N N2 0.5050(4) 0.3688(2) 0.43454(10) 0.0634(8) Uani d . 1 . .
N N3 0.3420(5) 0.3270(3) 0.44279(12) 0.0804(10) Uani d . 1 . .
N N4 0.2291(4) 0.3870(3) 0.41648(11) 0.0748(9) Uani d . 1 . .
C C1 0.1069(4) 0.7079(3) 0.29478(10) 0.0473(7) Uani d . 1 . .
C C2 0.2904(5) 0.7098(3) 0.30746(12) 0.0600(9) Uani d . 1 . .
H H2 0.3668 0.7655 0.2942 0.072 Uiso calc R 1 . .
C C3 0.3639(5) 0.6321(3) 0.33902(12) 0.0604(9) Uani d . 1 . .
H H3 0.4883 0.6361 0.3465 0.072 Uiso calc R 1 . .
C C4 0.2560(4) 0.5490(3) 0.35956(10) 0.0489(8) Uani d . 1 . .
C C5 0.0720(5) 0.5455(3) 0.34793(12) 0.0679(10) Uani d . 1 . .
H H5 -0.0042 0.4903 0.3617 0.082 Uiso calc R 1 . .
C C6 0.0004(5) 0.6231(3) 0.31617(12) 0.0663(10) Uani d . 1 . .
H H6 -0.1239 0.6186 0.3087 0.080 Uiso calc R 1 . .
C C7 0.3320(5) 0.4640(3) 0.39285(10) 0.0512(8) Uani d . 1 . .
C C8 0.6736(6) 0.3243(3) 0.45759(14) 0.0759(11) Uani d . 1 . .
H H8 0.6317 0.2726 0.4828 0.091 Uiso calc R 1 . .
C C9 0.7768(6) 0.4185(4) 0.48099(16) 0.0952(15) Uani d . 1 . .
H H9A 0.8732 0.3859 0.4999 0.143 Uiso calc R 1 . .
H H9B 0.6949 0.4622 0.5007 0.143 Uiso calc R 1 . .
H H9C 0.8292 0.4687 0.4576 0.143 Uiso calc R 1 . .
C C10 0.7788(6) 0.2512(4) 0.42484(17) 0.1005(15) Uani d . 1 . .
H H10A 0.6997 0.1925 0.4120 0.151 Uiso calc R 1 . .
H H10B 0.8788 0.2151 0.4413 0.151 Uiso calc R 1 . .
H H10C 0.8264 0.2982 0.3998 0.151 Uiso calc R 1 . .
C C11 0.1814(6) 0.8966(3) 0.22270(15) 0.0823(13) Uani d . 1 . .
H H11A 0.2715 0.8474 0.2082 0.123 Uiso calc R 1 . .
H H11B 0.2394 0.9431 0.2464 0.123 Uiso calc R 1 . .
H H11C 0.1273 0.9461 0.1994 0.123 Uiso calc R 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'
Si Si 0.0817 0.0704 '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
C11 Si1 C11 . 3 111.4(3) ?
C11 Si1 C1 . 3 110.56(16) ?
C11 Si1 C1 3 3 109.28(16) ?
C11 Si1 C1 . . 109.28(16) ?
C11 Si1 C1 3 . 110.56(16) ?
C1 Si1 C1 3 . 105.63(19) ?
C7 N1 N2 . . 100.9(3) ?
N3 N2 N1 . . 114.6(3) ?
N3 N2 C8 . . 123.1(3) ?
N1 N2 C8 . . 122.4(3) ?
N2 N3 N4 . . 105.8(3) ?
N3 N4 C7 . . 106.6(3) ?
C2 C1 C6 . . 115.8(3) ?
C2 C1 Si1 . . 124.7(2) ?
C6 C1 Si1 . . 119.5(2) ?
C3 C2 C1 . . 122.4(3) ?
C3 C2 H2 . . 118.8 ?
C1 C2 H2 . . 118.8 ?
C4 C3 C2 . . 120.7(3) ?
C4 C3 H3 . . 119.6 ?
C2 C3 H3 . . 119.6 ?
C3 C4 C5 . . 118.3(3) ?
C3 C4 C7 . . 121.7(3) ?
C5 C4 C7 . . 120.0(3) ?
C6 C5 C4 . . 120.4(3) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C5 C6 C1 . . 122.4(3) ?
C5 C6 H6 . . 118.8 ?
C1 C6 H6 . . 118.8 ?
N1 C7 N4 . . 112.1(3) ?
N1 C7 C4 . . 124.2(3) ?
N4 C7 C4 . . 123.6(3) ?
C10 C8 C9 . . 116.3(4) ?
C10 C8 N2 . . 110.4(3) ?
C9 C8 N2 . . 111.3(3) ?
C10 C8 H8 . . 106.0 ?
C9 C8 H8 . . 106.0 ?
N2 C8 H8 . . 106.0 ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C8 C10 H10A . . 109.5 ?
C8 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C8 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
Si1 C11 H11A . . 109.5 ?
Si1 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
Si1 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 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
Si1 C11 . 1.853(4) ?
Si1 C11 3 1.853(4) ?
Si1 C1 3 1.873(3) ?
Si1 C1 . 1.873(3) ?
N1 C7 . 1.324(4) ?
N1 N2 . 1.332(4) ?
N2 N3 . 1.301(4) ?
N2 C8 . 1.483(4) ?
N3 N4 . 1.309(4) ?
N4 C7 . 1.342(4) ?
C1 C2 . 1.382(4) ?
C1 C6 . 1.388(4) ?
C2 C3 . 1.377(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.370(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.379(4) ?
C4 C7 . 1.471(4) ?
C5 C6 . 1.374(5) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C8 C10 . 1.471(6) ?
C8 C9 . 1.479(5) ?
C8 H8 . 0.9800 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 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
C9 H9B Cg 5_666 0.96 2.86 3.738(5) 152
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
C7 N1 N2 N3 . . . . -0.1(4) ?
C7 N1 N2 C8 . . . . 179.8(3) ?
N1 N2 N3 N4 . . . . 0.0(4) ?
C8 N2 N3 N4 . . . . -180.0(3) ?
N2 N3 N4 C7 . . . . 0.2(4) ?
C11 Si1 C1 C2 . . . . 4.3(3) ?
C11 Si1 C1 C2 3 . . . -118.6(3) ?
C1 Si1 C1 C2 3 . . . 123.2(3) ?
C11 Si1 C1 C6 . . . . -173.0(3) ?
C11 Si1 C1 C6 3 . . . 64.1(3) ?
C1 Si1 C1 C6 3 . . . -54.0(2) ?
C6 C1 C2 C3 . . . . 0.5(5) ?
Si1 C1 C2 C3 . . . . -176.9(3) ?
C1 C2 C3 C4 . . . . -0.3(5) ?
C2 C3 C4 C5 . . . . -0.2(5) ?
C2 C3 C4 C7 . . . . 179.1(3) ?
C3 C4 C5 C6 . . . . 0.6(5) ?
C7 C4 C5 C6 . . . . -178.7(3) ?
C4 C5 C6 C1 . . . . -0.5(6) ?
C2 C1 C6 C5 . . . . -0.1(5) ?
Si1 C1 C6 C5 . . . . 177.4(3) ?
N2 N1 C7 N4 . . . . 0.2(4) ?
N2 N1 C7 C4 . . . . 179.4(3) ?
N3 N4 C7 N1 . . . . -0.3(4) ?
N3 N4 C7 C4 . . . . -179.4(3) ?
C3 C4 C7 N1 . . . . -4.4(5) ?
C5 C4 C7 N1 . . . . 174.9(3) ?
C3 C4 C7 N4 . . . . 174.7(3) ?
C5 C4 C7 N4 . . . . -6.0(5) ?
N3 N2 C8 C10 . . . . 103.6(4) ?
N1 N2 C8 C10 . . . . -76.3(5) ?
N3 N2 C8 C9 . . . . -125.6(4) ?
N1 N2 C8 C9 . . . . 54.4(5) ?
