#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/63/2206336.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_2206336
loop_
_publ_author_name
'Wei Wang'
'Bing Zhao'
'Peng-Wu Zheng'
'Xue-Min Duan'
_publ_section_title
;
 Bis[2-(1-phenyl-1H-tetrazol-5-ylsulfanyl)ethoxy] ether
;
_journal_coeditor_code           AT6021
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2623
_journal_page_last               o2624
_journal_paper_doi               10.1107/S160053680502249X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C20 H22 N8 O2 S2'
_chemical_formula_moiety         'C20 H22 N8 O2 S2'
_chemical_formula_sum            'C20 H22 N8 O2 S2'
_chemical_formula_weight         470.60
_chemical_melting_point          398
_chemical_name_systematic
;
Bis[2-(1-phenyl-1H-tetrazol-5-ylsulfanyl)ethoxy] ether
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.929(5)
_cell_length_b                   8.2223(16)
_cell_length_c                   18.737(6)
_cell_measurement_reflns_used    2662
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.18
_cell_measurement_theta_min      2.57
_cell_volume                     2300.0(12)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.070
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12227
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.01
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2356
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.01
_refine_ls_R_factor_all          0.091
_refine_ls_R_factor_gt           0.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0575P)²+0.95P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          1.101
_refine_ls_wR_factor_ref         0.128
_reflns_number_gt                1429
_reflns_number_total             2356
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at6021.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2206336
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_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_type_symbol
S1 0.17416(4) 0.21193(10) 0.25982(3) 0.0440(2) Uani d . 1 S
O1 0.06129(14) 0.3699(3) 0.44061(10) 0.0596(6) Uani d . 1 O
N1 0.32132(16) 0.3016(3) 0.33927(12) 0.0454(6) Uani d . 1 N
N2 0.41120(17) 0.3097(3) 0.32744(13) 0.0539(7) Uani d . 1 N
N3 0.43159(15) 0.2681(3) 0.26312(13) 0.0514(6) Uani d . 1 N
N4 0.35254(14) 0.2300(3) 0.22993(11) 0.0373(5) Uani d . 1 N
C1 0.0163(2) 0.5141(4) 0.46286(16) 0.0639(10) Uani d . 1 C
H1A -0.0336 0.5370 0.4314 0.077 Uiso calc R 1 H
H1B 0.0571 0.6059 0.4617 0.077 Uiso calc R 1 H
C2 0.0995(2) 0.3857(4) 0.37217(14) 0.0500(8) Uani d . 1 C
H2A 0.1502 0.4594 0.3737 0.060 Uiso calc R 1 H
H2B 0.0558 0.4283 0.3388 0.060 Uiso calc R 1 H
C3 0.12926(19) 0.2185(3) 0.34970(13) 0.0427(7) Uani d . 1 C
H3A 0.0786 0.1449 0.3527 0.051 Uiso calc R 1 H
H3B 0.1747 0.1803 0.3827 0.051 Uiso calc R 1 H
C4 0.28641(17) 0.2517(3) 0.27823(13) 0.0350(6) Uani d . 1 C
C5 0.35038(17) 0.1762(3) 0.15739(13) 0.0380(7) Uani d . 1 C
C6 0.2968(2) 0.2555(4) 0.10911(15) 0.0612(9) Uani d . 1 C
H6 0.2614 0.3426 0.1234 0.073 Uiso calc R 1 H
C7 0.2962(3) 0.2035(5) 0.03861(17) 0.0753(11) Uani d . 1 C
H7 0.2596 0.2549 0.0054 0.090 Uiso calc R 1 H
C8 0.3496(3) 0.0766(5) 0.01787(16) 0.0654(10) Uani d . 1 C
H8 0.3498 0.0434 -0.0296 0.078 Uiso calc R 1 H
C9 0.4027(2) -0.0016(4) 0.06656(17) 0.0554(8) Uani d . 1 C
H9 0.4390 -0.0873 0.0520 0.066 Uiso calc R 1 H
C10 0.40246(18) 0.0462(3) 0.13699(14) 0.0437(7) Uani d . 1 C
H10 0.4371 -0.0087 0.1704 0.052 Uiso calc R 1 H
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
;
O O 0.0106 0.0060
; 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 S1 C3 . . 99.57(12) ?
C2 O1 C1 . . 112.3(2) ?
C4 N1 N2 . . 105.2(2) ?
N3 N2 N1 . . 111.8(2) ?
N2 N3 N4 . . 106.4(2) ?
C4 N4 N3 . . 107.2(2) ?
C4 N4 C5 . . 131.4(2) ?
N3 N4 C5 . . 121.4(2) ?
O1 C1 C1 . 5_566 107.3(3) ?
O1 C1 H1A . . 110.3 ?
C1 C1 H1A 5_566 . 110.3 ?
O1 C1 H1B . . 110.3 ?
C1 C1 H1B 5_566 . 110.3 ?
H1A C1 H1B . . 108.5 ?
O1 C2 C3 . . 106.8(2) ?
O1 C2 H2A . . 110.4 ?
C3 C2 H2A . . 110.4 ?
O1 C2 H2B . . 110.4 ?
C3 C2 H2B . . 110.4 ?
H2A C2 H2B . . 108.6 ?
C2 C3 S1 . . 113.35(19) ?
C2 C3 H3A . . 108.9 ?
S1 C3 H3A . . 108.9 ?
C2 C3 H3B . . 108.9 ?
S1 C3 H3B . . 108.9 ?
H3A C3 H3B . . 107.7 ?
N1 C4 N4 . . 109.4(2) yes
N1 C4 S1 . . 127.5(2) yes
N4 C4 S1 . . 123.06(19) ?
C6 C5 C10 . . 121.0(3) ?
C6 C5 N4 . . 119.5(2) ?
C10 C5 N4 . . 119.4(2) ?
C5 C6 C7 . . 119.0(3) ?
C5 C6 H6 . . 120.5 ?
C7 C6 H6 . . 120.5 ?
C8 C7 C6 . . 120.1(3) ?
C8 C7 H7 . . 120.0 ?
C6 C7 H7 . . 120.0 ?
C7 C8 C9 . . 120.4(3) ?
C7 C8 H8 . . 119.8 ?
C9 C8 H8 . . 119.8 ?
C8 C9 C10 . . 120.2(3) ?
C8 C9 H9 . . 119.9 ?
C10 C9 H9 . . 119.9 ?
C5 C10 C9 . . 119.3(3) ?
C5 C10 H10 . . 120.3 ?
C9 C10 H10 . . 120.3 ?
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
S1 C4 . 1.742(3) yes
S1 C3 . 1.813(2) yes
O1 C2 . 1.410(3) ?
O1 C1 . 1.425(3) ?
N1 C4 . 1.322(3) ?
N1 N2 . 1.362(3) ?
N2 N3 . 1.289(3) ?
N3 N4 . 1.370(3) ?
N4 C4 . 1.351(3) ?
N4 C5 . 1.430(3) ?
C1 C1 5_566 1.493(6) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 C3 . 1.505(4) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C5 C6 . 1.372(4) ?
C5 C10 . 1.376(4) ?
C6 C7 . 1.388(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.369(5) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.369(5) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.377(4) ?
C9 H9 . 0.9300 ?
C10 H10 . 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_site_symmetry_4
_geom_torsion
C4 N1 N2 N3 . 0.1(3)
N1 N2 N3 N4 . -0.1(3)
N2 N3 N4 C4 . 0.0(3)
N2 N3 N4 C5 . -179.2(2)
C2 O1 C1 C1 5_566 -176.7(3)
C1 O1 C2 C3 . -169.7(3)
O1 C2 C3 S1 . 176.30(19)
C4 S1 C3 C2 . 89.4(2)
N2 N1 C4 N4 . -0.2(3)
N2 N1 C4 S1 . 178.1(2)
N3 N4 C4 N1 . 0.1(3)
C5 N4 C4 N1 . 179.2(3)
N3 N4 C4 S1 . -178.19(19)
C5 N4 C4 S1 . 0.9(4)
C3 S1 C4 N1 . -10.9(3)
C3 S1 C4 N4 . 167.1(2)
C4 N4 C5 C6 . 55.1(4)
N3 N4 C5 C6 . -125.9(3)
C4 N4 C5 C10 . -125.2(3)
N3 N4 C5 C10 . 53.8(3)
C10 C5 C6 C7 . -0.6(5)
N4 C5 C6 C7 . 179.1(3)
C5 C6 C7 C8 . -1.0(6)
C6 C7 C8 C9 . 1.1(6)
C7 C8 C9 C10 . 0.3(5)
C6 C5 C10 C9 . 2.0(4)
N4 C5 C10 C9 . -177.7(2)
C8 C9 C10 C5 . -1.9(4)
