#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/82/2228200.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_2228200
loop_
_publ_author_name
'Wang, Wei'
'Qiu, Hong'
'Gao, Yan'
'Yao, Hong-Guo'
'Ji, Ming'
_publ_section_title
;
 5,5'-Diphenyl-2,2'-[butane-1,4-diylbis(sulfanediyl)]bis(1,3,4-oxadiazole)
;
_journal_coeditor_code           ZS2072
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2931
_journal_paper_doi               10.1107/S1600536810042315
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H18 N4 O2 S2'
_chemical_formula_moiety         'C20 H18 N4 O2 S2'
_chemical_formula_sum            'C20 H18 N4 O2 S2'
_chemical_formula_weight         410.50
_chemical_name_common
;
1,4-bis(5-phenyl-1,3,4-oxadiazol-2-ylsulfanyl)butane
;
_chemical_name_systematic
;
5,5'-diphenyl-2,2'-[butane-1,4-diylbis(sulfanediyl)]bis(1,3,4-oxadiazole)
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 104.04(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.202(2)
_cell_length_b                   5.9317(12)
_cell_length_c                   13.518(3)
_cell_measurement_reflns_used    3017
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.859
_cell_measurement_theta_min      1.720
_cell_volume                     949.2(3)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 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      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_sigmaI/netI    0.0516
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7030
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.70
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_T_max  0.9643
_exptl_absorpt_correction_T_min  0.9415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.329
_refine_ls_extinction_coef       0.067(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1661
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0403
_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)+(0.0778P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1279
_reflns_number_gt                1323
_reflns_number_total             1661
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2072.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228200
_cod_database_fobs_code          2228200
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
S S1 0.43518(5) 1.09305(10) 0.65529(4) 0.0256(3) Uani d . 1 . .
O O1 0.30541(12) 0.7504(3) 0.68093(12) 0.0210(4) Uani d . 1 . .
N N1 0.19647(17) 0.6825(3) 0.52644(14) 0.0265(5) Uani d . 1 . .
N N2 0.26743(17) 0.8685(3) 0.51955(14) 0.0242(5) Uani d . 1 . .
C C1 0.2073(2) 0.3923(4) 0.77192(18) 0.0278(6) Uani d . 1 . .
H H1 0.2568 0.4939 0.8155 0.033 Uiso calc R 1 . .
C C2 0.1655(2) 0.2040(4) 0.81204(19) 0.0292(6) Uani d . 1 . .
H H2 0.1869 0.1762 0.8834 0.035 Uiso calc R 1 . .
C C3 0.0925(2) 0.0563(4) 0.7481(2) 0.0291(6) Uani d . 1 . .
H H3 0.0657 -0.0740 0.7757 0.035 Uiso calc R 1 . .
C C4 0.0589(2) 0.0987(4) 0.64463(19) 0.0278(6) Uani d . 1 . .
H H4 0.0071 -0.0001 0.6016 0.033 Uiso calc R 1 . .
C C5 0.1004(2) 0.2843(4) 0.60345(18) 0.0258(6) Uani d . 1 . .
H H5 0.0778 0.3123 0.5322 0.031 Uiso calc R 1 . .
C C6 0.17557(19) 0.4300(4) 0.66720(17) 0.0185(6) Uani d . 1 . .
C C7 0.22137(19) 0.6207(4) 0.62076(17) 0.0193(6) Uani d . 1 . .
C C8 0.3285(2) 0.8996(4) 0.61119(17) 0.0214(6) Uani d . 1 . .
C C9 0.4184(2) 1.2482(4) 0.53652(18) 0.0235(6) Uani d . 1 . .
H H9A 0.4274 1.1445 0.4817 0.028 Uiso calc R 1 . .
H H9B 0.3417 1.3145 0.5166 0.028 Uiso calc R 1 . .
C C10 0.5064(2) 1.4340(4) 0.55008(17) 0.0216(6) Uani d . 1 . .
H H10A 0.5829 1.3674 0.5705 0.026 Uiso calc R 1 . .
H H10B 0.4970 1.5378 0.6048 0.026 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
;
O O 0.0106 0.0060
; International Tables
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
S S 0.1246 0.1246
; International Tables
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
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
C8 S1 C9 . . 96.73(11) ?
C8 O1 C7 . . 101.66(17) ?
C7 N1 N2 . . 106.53(18) ?
C8 N2 N1 . . 105.48(18) ?
C2 C1 C6 . . 119.2(2) ?
C2 C1 H1 . . 120.4 ?
C6 C1 H1 . . 120.4 ?
C3 C2 C1 . . 120.2(2) ?
C3 C2 H2 . . 119.9 ?
C1 C2 H2 . . 119.9 ?
C4 C3 C2 . . 120.2(2) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C3 C4 C5 . . 120.3(2) ?
C3 C4 H4 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
C4 C5 C6 . . 119.6(2) ?
C4 C5 H5 . . 120.2 ?
C6 C5 H5 . . 120.2 ?
C1 C6 C5 . . 120.5(2) ?
C1 C6 C7 . . 121.2(2) ?
C5 C6 C7 . . 118.3(2) ?
N1 C7 O1 . . 112.81(19) ?
N1 C7 C6 . . 128.2(2) ?
O1 C7 C6 . . 118.9(2) ?
N2 C8 O1 . . 113.5(2) ?
N2 C8 S1 . . 129.42(18) ?
O1 C8 S1 . . 117.02(17) ?
C10 C9 S1 . . 109.62(17) ?
C10 C9 H9A . . 109.7 ?
S1 C9 H9A . . 109.7 ?
C10 C9 H9B . . 109.7 ?
S1 C9 H9B . . 109.7 ?
H9A C9 H9B . . 108.2 ?
C9 C10 C10 . 3_686 110.2(2) ?
C9 C10 H10A . . 109.6 ?
C10 C10 H10A 3_686 . 109.6 ?
C9 C10 H10B . . 109.6 ?
C10 C10 H10B 3_686 . 109.6 ?
H10A C10 H10B . . 108.1 ?
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 C8 . 1.729(2) ?
S1 C9 . 1.818(2) ?
O1 C8 . 1.371(3) ?
O1 C7 . 1.378(3) ?
N1 C7 . 1.290(3) ?
N1 N2 . 1.419(3) ?
N2 C8 . 1.295(3) ?
C1 C2 . 1.391(3) ?
C1 C6 . 1.392(3) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.390(4) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.382(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.384(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.396(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.468(3) ?
C9 C10 . 1.518(3) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C10 3_686 1.539(4) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
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 C8 . . . . 0.1(2) ?
C6 C1 C2 C3 . . . . -0.4(4) ?
C1 C2 C3 C4 . . . . -1.5(4) ?
C2 C3 C4 C5 . . . . 2.0(4) ?
C3 C4 C5 C6 . . . . -0.6(4) ?
C2 C1 C6 C5 . . . . 1.8(3) ?
C2 C1 C6 C7 . . . . -177.2(2) ?
C4 C5 C6 C1 . . . . -1.3(3) ?
C4 C5 C6 C7 . . . . 177.7(2) ?
N2 N1 C7 O1 . . . . -0.1(2) ?
N2 N1 C7 C6 . . . . -177.1(2) ?
C8 O1 C7 N1 . . . . 0.1(2) ?
C8 O1 C7 C6 . . . . 177.40(19) ?
C1 C6 C7 N1 . . . . -176.7(2) ?
C5 C6 C7 N1 . . . . 4.3(4) ?
C1 C6 C7 O1 . . . . 6.5(3) ?
C5 C6 C7 O1 . . . . -172.54(19) ?
N1 N2 C8 O1 . . . . -0.1(3) ?
N1 N2 C8 S1 . . . . 177.74(17) ?
C7 O1 C8 N2 . . . . 0.0(2) ?
C7 O1 C8 S1 . . . . -178.11(15) ?
C9 S1 C8 N2 . . . . 6.4(2) ?
C9 S1 C8 O1 . . . . -175.89(17) ?
C8 S1 C9 C10 . . . . -178.33(17) ?
S1 C9 C10 C10 . . . 3_686 179.7(2) ?
