#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/19/8101956.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8101956
loop_
_publ_author_name
'Zhang, G.-F.'
'Dou, Y.-L.'
'She, J.-B.'
'Zhao, S.-M.'
'Liu, H.-Q.'
_publ_section_title
;
Crystal structure of 1,3-bis(1-phenyl-1H-tetrazol-5-ylthio)propane, 
C₃H₆(SCN₄C₆H₅)₂
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              185
_journal_page_last               186
_journal_volume                  221
_journal_year                    2006
_chemical_formula_moiety         'C17 H16 N8 S2'
_chemical_formula_sum            'C17 H16 N8 S2'
_chemical_formula_weight         396.50
_chemical_name_systematic
; 
 1,3-bis(1-phenyl-1H-tetrazol-5-ylthio)propane
;
_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                 112.126(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.716(5)
_cell_length_b                   6.4919(19)
_cell_length_c                   18.640(6)
_cell_measurement_reflns_used    1109
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.252
_cell_measurement_theta_min      2.631
_cell_volume                     1873.8(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       phi/omega
_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  0.0875
_diffrn_reflns_av_sigmaI/netI    0.1066
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9385
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.40
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_T_max  0.9644
_exptl_absorpt_correction_T_min  0.8504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3294
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1280
_refine_ls_R_factor_gt           0.0521
_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)+(0.0395P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1282
_reflns_number_gt                1615
_reflns_number_total             3294
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-1760.cff
_cod_data_source_block           060404e
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        1873.8(9)
_cod_original_sg_symbol_H-M      P12(1)/n1
_cod_database_code               8101956
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.04582(18) 0.7693(5) 1.08313(16) 0.0381(8) Uani 1 4 e d . . .
N2 N -0.0412(2) 0.7573(5) 1.05584(18) 0.0462(9) Uani 1 4 e d . . .
N3 N -0.06656(19) 0.7356(5) 0.98173(19) 0.0491(9) Uani 1 4 e d . . .
N4 N 0.00204(19) 0.7348(5) 0.95859(16) 0.0425(8) Uani 1 4 e d . . .
N5 N 0.1068(2) 1.1641(5) 0.65259(17) 0.0466(9) Uani 1 4 e d . . .
N6 N 0.1408(2) 1.0614(6) 0.60686(19) 0.0636(11) Uani 1 4 e d . . .
N7 N 0.1950(2) 0.9305(7) 0.6514(2) 0.0713(12) Uani 1 4 e d . . .
N8 N 0.1975(2) 0.9394(6) 0.72557(18) 0.0553(10) Uani 1 4 e d . . .
S1 S 0.17870(6) 0.76499(18) 1.03344(5) 0.0486(3) Uani 1 4 e d . . .
S2 S 0.11121(7) 1.16743(18) 0.79837(6) 0.0545(4) Uani 1 4 e d . . .
C1 C 0.1734(2) 0.6566(6) 0.9420(2) 0.0496(11) Uani 1 4 e d . . .
H1A H 0.2317 0.6248 0.9463 0.059 Uiso 1 4 e calc R . .
H1B H 0.1419 0.5277 0.9338 0.059 Uiso 1 4 e calc R . .
C2 C 0.1316(2) 0.7910(6) 0.8713(2) 0.0514(12) Uani 1 4 e d . . .
H2A H 0.1318 0.7172 0.8261 0.062 Uiso 1 4 e calc R . .
H2B H 0.0718 0.8142 0.8644 0.062 Uiso 1 4 e calc R . .
C3 C 0.1745(2) 0.9962(6) 0.8749(2) 0.0469(11) Uani 1 4 e d . . .
H3A H 0.2304 0.9751 0.8714 0.056 Uiso 1 4 e calc R . .
H3B H 0.1841 1.0602 0.9245 0.056 Uiso 1 4 e calc R . .
C4 C 0.0715(2) 0.7546(6) 1.0230(2) 0.0383(10) Uani 1 4 e d . . .
C5 C 0.0958(2) 0.7835(7) 1.1650(2) 0.0420(10) Uani 1 4 e d . . .
C6 C 0.0978(3) 0.6185(7) 1.2110(2) 0.0617(13) Uani 1 4 e d . . .
H6 H 0.0685 0.4978 1.1898 0.074 Uiso 1 4 e calc R . .
C7 C 0.1445(3) 0.6343(9) 1.2899(3) 0.0793(17) Uani 1 4 e d . . .
H7 H 0.1464 0.5239 1.3223 0.095 Uiso 1 4 e calc R . .
C8 C 0.1878(3) 0.8116(10) 1.3202(3) 0.0795(17) Uani 1 4 e d . . .
H8 H 0.2196 0.8211 1.3731 0.095 Uiso 1 4 e calc R . .
C9 C 0.1846(3) 0.9753(8) 1.2732(3) 0.0755(15) Uani 1 4 e d . . .
H9 H 0.2137 1.0962 1.2946 0.091 Uiso 1 4 e calc R . .
C10 C 0.1383(3) 0.9630(7) 1.1939(2) 0.0611(13) Uani 1 4 e d . . .
H10 H 0.1364 1.0735 1.1616 0.073 Uiso 1 4 e calc R . .
C11 C 0.1416(2) 1.0858(6) 0.7241(2) 0.0411(10) Uani 1 4 e d . . .
C12 C 0.0428(3) 1.3204(8) 0.6224(2) 0.0463(11) Uani 1 4 e d . . .
C13 C 0.0559(3) 1.5104(8) 0.6565(2) 0.0589(13) Uani 1 4 e d . . .
H13 H 0.1065 1.5385 0.6986 0.071 Uiso 1 4 e calc R . .
C14 C -0.0062(3) 1.6592(8) 0.6280(3) 0.0752(15) Uani 1 4 e d . . .
H14 H 0.0012 1.7879 0.6516 0.090 Uiso 1 4 e calc R . .
C15 C -0.0799(3) 1.6169(10) 0.5642(3) 0.0849(19) Uani 1 4 e d . . .
H15 H -0.1214 1.7188 0.5443 0.102 Uiso 1 4 e calc R . .
C16 C -0.0925(3) 1.4282(11) 0.5302(3) 0.0825(18) Uani 1 4 e d . . .
H16 H -0.1426 1.4019 0.4873 0.099 Uiso 1 4 e calc R . .
C17 C -0.0311(3) 1.2749(8) 0.5592(2) 0.0623(13) Uani 1 4 e d . . .
H17 H -0.0394 1.1448 0.5367 0.075 Uiso 1 4 e calc R . .
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'
S S 0.1246 0.1234 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 N2 108.6(3) . . ?
C4 N1 C5 130.3(3) . . ?
N2 N1 C5 121.0(3) . . ?
N3 N2 N1 106.4(3) . . ?
N2 N3 N4 111.2(3) . . ?
C4 N4 N3 105.4(3) . . ?
C11 N5 N6 108.0(3) . . ?
C11 N5 C12 130.1(3) . . ?
N6 N5 C12 121.9(3) . . ?
N7 N6 N5 106.1(3) . . ?
N6 N7 N8 111.6(3) . . ?
C11 N8 N7 104.9(3) . . ?
C4 S1 C1 101.41(18) . . ?
C11 S2 C3 100.51(19) . . ?
C2 C1 S1 115.9(3) . . ?
C2 C1 H1A 108.3 . . ?
S1 C1 H1A 108.3 . . ?
C2 C1 H1B 108.3 . . ?
S1 C1 H1B 108.3 . . ?
H1A C1 H1B 107.4 . . ?
C3 C2 C1 114.6(3) . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
C1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
C2 C3 S2 112.5(3) . . ?
C2 C3 H3A 109.1 . . ?
S2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
S2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
N4 C4 N1 108.4(3) . . ?
N4 C4 S1 128.5(3) . . ?
N1 C4 S1 123.1(3) . . ?
C6 C5 C10 122.4(4) . . ?
C6 C5 N1 118.8(4) . . ?
C10 C5 N1 118.7(4) . . ?
C5 C6 C7 118.7(5) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C8 C7 C6 120.0(5) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 120.4(4) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 120.6(5) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C5 C10 C9 117.9(4) . . ?
C5 C10 H10 121.1 . . ?
C9 C10 H10 121.1 . . ?
N8 C11 N5 109.4(3) . . ?
N8 C11 S2 128.4(3) . . ?
N5 C11 S2 122.2(3) . . ?
C13 C12 C17 121.7(4) . . ?
C13 C12 N5 119.6(4) . . ?
C17 C12 N5 118.8(4) . . ?
C12 C13 C14 119.4(5) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C15 119.6(5) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 120.9(5) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 120.2(5) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 118.2(5) . . ?
C12 C17 H17 120.9 . . ?
C16 C17 H17 120.9 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C4 1.346(4) . ?
N1 N2 1.351(4) . ?
N1 C5 1.441(4) . ?
N2 N3 1.291(4) . ?
N3 N4 1.369(4) . ?
N4 C4 1.326(4) . ?
N5 C11 1.338(4) . ?
N5 N6 1.364(4) . ?
N5 C12 1.427(5) . ?
N6 N7 1.290(4) . ?
N7 N8 1.369(4) . ?
N8 C11 1.325(5) . ?
S1 C4 1.729(4) . ?
S1 C1 1.815(4) . ?
S2 C11 1.728(4) . ?
S2 C3 1.803(4) . ?
C1 C2 1.515(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.502(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 C6 1.364(5) . ?
C5 C10 1.366(5) . ?
C6 C7 1.386(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.363(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.365(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C12 C13 1.367(5) . ?
C12 C17 1.380(5) . ?
C13 C14 1.371(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.359(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.385(6) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 N2 N3 0.2(4) . . . . ?
C5 N1 N2 N3 -176.7(3) . . . . ?
N1 N2 N3 N4 -0.6(4) . . . . ?
N2 N3 N4 C4 0.8(4) . . . . ?
C11 N5 N6 N7 -1.2(5) . . . . ?
C12 N5 N6 N7 -179.1(4) . . . . ?
N5 N6 N7 N8 1.0(5) . . . . ?
N6 N7 N8 C11 -0.5(5) . . . . ?
C4 S1 C1 C2 71.4(3) . . . . ?
S1 C1 C2 C3 59.0(4) . . . . ?
C1 C2 C3 S2 -169.2(3) . . . . ?
C11 S2 C3 C2 -83.8(3) . . . . ?
N3 N4 C4 N1 -0.7(4) . . . . ?
N3 N4 C4 S1 -179.8(3) . . . . ?
N2 N1 C4 N4 0.3(4) . . . . ?
C5 N1 C4 N4 176.8(4) . . . . ?
N2 N1 C4 S1 179.5(3) . . . . ?
C5 N1 C4 S1 -3.9(6) . . . . ?
C1 S1 C4 N4 -18.4(4) . . . . ?
C1 S1 C4 N1 162.5(3) . . . . ?
C4 N1 C5 C6 -108.8(5) . . . . ?
N2 N1 C5 C6 67.4(5) . . . . ?
C4 N1 C5 C10 72.2(5) . . . . ?
N2 N1 C5 C10 -111.6(4) . . . . ?
C10 C5 C6 C7 0.3(6) . . . . ?
N1 C5 C6 C7 -178.7(4) . . . . ?
C5 C6 C7 C8 -0.5(7) . . . . ?
C6 C7 C8 C9 0.8(8) . . . . ?
C7 C8 C9 C10 -0.9(8) . . . . ?
C6 C5 C10 C9 -0.4(6) . . . . ?
N1 C5 C10 C9 178.6(3) . . . . ?
C8 C9 C10 C5 0.7(7) . . . . ?
N7 N8 C11 N5 -0.3(4) . . . . ?
N7 N8 C11 S2 177.4(3) . . . . ?
N6 N5 C11 N8 0.9(5) . . . . ?
C12 N5 C11 N8 178.6(4) . . . . ?
N6 N5 C11 S2 -177.0(3) . . . . ?
C12 N5 C11 S2 0.7(6) . . . . ?
C3 S2 C11 N8 -1.0(4) . . . . ?
C3 S2 C11 N5 176.5(3) . . . . ?
C11 N5 C12 C13 56.1(6) . . . . ?
N6 N5 C12 C13 -126.5(4) . . . . ?
C11 N5 C12 C17 -123.8(4) . . . . ?
N6 N5 C12 C17 53.6(5) . . . . ?
C17 C12 C13 C14 0.9(6) . . . . ?
N5 C12 C13 C14 -179.1(4) . . . . ?
C12 C13 C14 C15 -1.8(7) . . . . ?
C13 C14 C15 C16 1.4(8) . . . . ?
C14 C15 C16 C17 -0.2(8) . . . . ?
C13 C12 C17 C16 0.3(6) . . . . ?
N5 C12 C17 C16 -179.7(4) . . . . ?
C15 C16 C17 C12 -0.7(7) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3169715
