#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/22/2202254.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_2202254
loop_
_publ_author_name
'Ruqiang Zou'
'Jian-Rong Li'
'Yan Zheng'
'Ruo-Hua Zhang'
'Xian-He Bu'
_publ_section_title
;
 1,2-Bis(benzothiazol-2-ylsulfanyl)ethane
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o393
_journal_page_last               o394
_journal_paper_doi               10.1107/S1600536803004264
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C16 H12 N2 S4'
_chemical_formula_moiety         'C16 H12 N2 S4'
_chemical_formula_sum            'C16 H12 N2 S4'
_chemical_formula_weight         360.53
_chemical_name_systematic
;
1,2-bis(benzothiazol-2-ylsulfanyl)ethane
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 114.029(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.534(4)
_cell_length_b                   10.719(4)
_cell_length_c                   14.006(5)
_cell_measurement_reflns_used    719
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.6
_cell_measurement_theta_min      3.7
_cell_volume                     1581.5(10)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_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 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  0.037
_diffrn_reflns_av_sigmaI/netI    0.049
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6363
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         1.9
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.60
_exptl_absorpt_correction_T_max  0.890
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.00
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2791
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.00
_refine_ls_R_factor_all          0.075
_refine_ls_R_factor_gt           0.039
_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)+(0.0413P)²+0.2548P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.081
_refine_ls_wR_factor_ref         0.094
_reflns_number_gt                1833
_reflns_number_total             2791
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ya6152.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Yes' changed to 'yes' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (12 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Yes' changed to 'yes' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (12
times).

'_geom_angle_publ_flag' value 'Yes' changed to 'yes'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (2
times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2202254
_cod_database_fobs_code          2202254
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_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
_atom_site_type_symbol
S1 0.71656(7) 0.53816(7) 0.11326(6) 0.0529(2) Uani d . 1 . . S
S2 0.73711(8) 0.40329(8) 0.30512(6) 0.0618(3) Uani d . 1 . . S
S3 0.43280(8) 0.33636(8) 0.41476(7) 0.0626(3) Uani d . 1 . . S
S4 0.43831(7) 0.19798(8) 0.59982(6) 0.0591(3) Uani d . 1 . . S
N1 0.5573(2) 0.5757(2) 0.19906(17) 0.0461(6) Uani d . 1 . . N
N2 0.6112(2) 0.1659(2) 0.52809(18) 0.0466(6) Uani d . 1 . . N
C1 0.5964(2) 0.6467(2) 0.0549(2) 0.0415(7) Uani d . 1 . . C
C2 0.5719(3) 0.7194(3) -0.0323(2) 0.0533(8) Uani d . 1 . . C
H2 0.6217 0.7134 -0.0702 0.064 Uiso calc R 1 . . H
C3 0.4708(3) 0.8019(3) -0.0618(2) 0.0645(9) Uani d . 1 . . C
H3 0.4523 0.8518 -0.1205 0.077 Uiso calc R 1 . . H
C4 0.3975(3) 0.8107(3) -0.0054(3) 0.0639(9) Uani d . 1 . . C
H4 0.3305 0.8672 -0.0265 0.077 Uiso calc R 1 . . H
C5 0.4210(3) 0.7377(3) 0.0819(2) 0.0553(8) Uani d . 1 . . C
H5 0.3704 0.7443 0.1191 0.066 Uiso calc R 1 . . H
C6 0.5217(2) 0.6542(2) 0.1129(2) 0.0419(7) Uani d . 1 . . C
C7 0.6560(3) 0.5113(3) 0.2078(2) 0.0449(7) Uani d . 1 . . C
C8 0.6432(3) 0.4090(3) 0.3827(2) 0.0626(9) Uani d . 1 . . C
H8A 0.6954 0.3826 0.4536 0.075 Uiso calc R 1 . . H
H8B 0.6169 0.4943 0.3856 0.075 Uiso calc R 1 . . H
C9 0.5291(3) 0.3279(3) 0.3388(2) 0.0595(8) Uani d . 1 . . C
H9A 0.5556 0.2422 0.3376 0.071 Uiso calc R 1 . . H
H9B 0.4780 0.3529 0.2674 0.071 Uiso calc R 1 . . H
C10 0.5096(3) 0.2275(3) 0.5127(2) 0.0459(7) Uani d . 1 . . C
C11 0.6412(3) 0.0865(2) 0.6133(2) 0.0425(7) Uani d . 1 . . C
C12 0.7435(3) 0.0061(3) 0.6508(2) 0.0523(8) Uani d . 1 . . C
H12 0.7989 0.0009 0.6179 0.063 Uiso calc R 1 . . H
C13 0.7629(3) -0.0663(3) 0.7374(2) 0.0600(8) Uani d . 1 . . C
H13 0.8327 -0.1193 0.7633 0.072 Uiso calc R 1 . . H
C14 0.6800(3) -0.0611(3) 0.7862(2) 0.0629(9) Uani d . 1 . . C
H14 0.6940 -0.1113 0.8440 0.075 Uiso calc R 1 . . H
C15 0.5769(3) 0.0179(3) 0.7498(2) 0.0586(8) Uani d . 1 . . C
H15 0.5215 0.0218 0.7828 0.070 Uiso calc R 1 . . H
C16 0.5575(3) 0.0913(3) 0.6633(2) 0.0467(7) Uani d . 1 . . C
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_publ_flag
C1 S1 C7 88.77(13) ?
C7 S2 C8 100.64(14) yes
C10 S3 C9 100.98(14) yes
C16 S4 C10 88.73(13) ?
C7 N1 C6 110.0(2) ?
C10 N2 C11 110.5(2) ?
C2 C1 C6 121.7(3) ?
C2 C1 S1 129.2(2) ?
C6 C1 S1 109.0(2) ?
C1 C2 C3 118.0(3) ?
C1 C2 H2 121.0 ?
C3 C2 H2 121.0 ?
C4 C3 C2 120.8(3) ?
C4 C3 H3 119.6 ?
C2 C3 H3 119.6 ?
C3 C4 C5 121.6(3) ?
C3 C4 H4 119.2 ?
C5 C4 H4 119.2 ?
C4 C5 C6 118.7(3) ?
C4 C5 H5 120.7 ?
C6 C5 H5 120.7 ?
C5 C6 N1 125.2(2) ?
C5 C6 C1 119.2(3) ?
N1 C6 C1 115.6(2) ?
N1 C7 S2 126.9(2) ?
N1 C7 S1 116.5(2) ?
S2 C7 S1 116.60(16) ?
C9 C8 S2 112.0(2) ?
C9 C8 H8A 109.2 ?
S2 C8 H8A 109.2 ?
C9 C8 H8B 109.2 ?
S2 C8 H8B 109.2 ?
H8A C8 H8B 107.9 ?
C8 C9 S3 112.1(2) ?
C8 C9 H9A 109.2 ?
S3 C9 H9A 109.2 ?
C8 C9 H9B 109.2 ?
S3 C9 H9B 109.2 ?
H9A C9 H9B 107.9 ?
N2 C10 S3 127.8(2) ?
N2 C10 S4 116.4(2) ?
S3 C10 S4 115.86(17) ?
C12 C11 N2 125.8(2) ?
C12 C11 C16 119.2(3) ?
N2 C11 C16 115.0(2) ?
C13 C12 C11 119.6(3) ?
C13 C12 H12 120.2 ?
C11 C12 H12 120.2 ?
C12 C13 C14 120.9(3) ?
C12 C13 H13 119.5 ?
C14 C13 H13 119.5 ?
C15 C14 C13 120.5(3) ?
C15 C14 H14 119.7 ?
C13 C14 H14 119.7 ?
C14 C15 C16 118.8(3) ?
C14 C15 H15 120.6 ?
C16 C15 H15 120.6 ?
C15 C16 C11 121.0(3) ?
C15 C16 S4 129.6(2) ?
C11 C16 S4 109.3(2) ?
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 C1 . 1.738(3) yes
S1 C7 . 1.754(3) yes
S2 C7 . 1.742(3) yes
S2 C8 . 1.821(3) yes
S3 C9 . 1.827(3) yes
S3 C10 . 1.743(3) yes
S4 C10 . 1.755(3) yes
S4 C16 . 1.730(3) yes
N1 C6 . 1.390(3) yes
N1 C7 . 1.294(3) yes
N2 C10 . 1.284(3) yes
N2 C11 . 1.391(3) yes
C1 C2 . 1.378(4) ?
C1 C6 . 1.406(3) ?
C2 C3 . 1.385(4) ?
C2 H2 . 0.93 ?
C3 C4 . 1.376(4) ?
C3 H3 . 0.93 ?
C4 C5 . 1.383(4) ?
C4 H4 . 0.93 ?
C5 C6 . 1.388(4) ?
C5 H5 . 0.93 ?
C8 C9 . 1.486(4) ?
C8 H8A . 0.97 ?
C8 H8B . 0.97 ?
C9 H9A . 0.97 ?
C9 H9B . 0.97 ?
C11 C12 . 1.380(4) ?
C11 C16 . 1.406(4) ?
C12 C13 . 1.379(4) ?
C12 H12 . 0.93 ?
C13 C14 . 1.385(4) ?
C13 H13 . 0.93 ?
C14 C15 . 1.377(4) ?
C14 H14 . 0.93 ?
C15 C16 . 1.384(4) ?
C15 H15 . 0.93 ?
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
C7 S1 C1 C2 179.5(3)
C7 S1 C1 C6 0.7(2)
C6 C1 C2 C3 0.3(4)
S1 C1 C2 C3 -178.4(2)
C1 C2 C3 C4 0.1(5)
C2 C3 C4 C5 -0.5(5)
C3 C4 C5 C6 0.4(5)
C4 C5 C6 N1 179.5(3)
C4 C5 C6 C1 0.0(4)
C7 N1 C6 C5 -178.8(3)
C7 N1 C6 C1 0.7(3)
C2 C1 C6 C5 -0.3(4)
S1 C1 C6 C5 178.6(2)
C2 C1 C6 N1 -179.9(2)
S1 C1 C6 N1 -1.0(3)
C6 N1 C7 S2 178.4(2)
C6 N1 C7 S1 -0.1(3)
C8 S2 C7 N1 0.7(3)
C8 S2 C7 S1 179.25(16)
C1 S1 C7 N1 -0.4(2)
C1 S1 C7 S2 -179.05(17)
C7 S2 C8 C9 83.2(2)
S2 C8 C9 S3 -178.60(15)
C10 S3 C9 C8 -84.6(2)
C11 N2 C10 S3 -179.0(2)
C11 N2 C10 S4 0.4(3)
C9 S3 C10 N2 3.9(3)
C9 S3 C10 S4 -175.54(16)
C16 S4 C10 N2 -0.2(2)
C16 S4 C10 S3 179.31(17)
C10 N2 C11 C12 179.3(3)
C10 N2 C11 C16 -0.6(3)
N2 C11 C12 C13 179.0(3)
C16 C11 C12 C13 -1.1(4)
C11 C12 C13 C14 1.1(5)
C12 C13 C14 C15 -0.8(5)
C13 C14 C15 C16 0.4(5)
C14 C15 C16 C11 -0.3(4)
C14 C15 C16 S4 179.9(2)
C12 C11 C16 C15 0.7(4)
N2 C11 C16 C15 -179.4(2)
C12 C11 C16 S4 -179.5(2)
N2 C11 C16 S4 0.4(3)
C10 S4 C16 C15 179.7(3)
C10 S4 C16 C11 -0.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 267535
