#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/04/2220477.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_2220477
loop_
_publ_author_name
'Wang, Guo-wei'
'Wu, Lin-ping'
'Zhuang, Ling-hua'
'Wang, Jin-tang'
_publ_section_title
;
 1,2-Bis(1,3-benzothiazol-2-yl)benzene
;
_journal_coeditor_code           DN2416
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o158
_journal_paper_doi               10.1107/S1600536808042542
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H12 N2 S2'
_chemical_formula_moiety         'C20 H12 N2 S2'
_chemical_formula_sum            'C20 H12 N2 S2'
_chemical_formula_weight         344.44
_chemical_name_systematic
;
1,2-Bis(1,3-benzothiazol-2-yl)benzene
;
_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                 100.77(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.748(2)
_cell_length_b                   19.148(4)
_cell_length_c                   8.1840(16)
_cell_measurement_reflns_used    27
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      1
_cell_volume                     1654.6(6)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia,
1997) and
PLATON (Spek, 2003)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0766
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3000
_diffrn_reflns_theta_full        25.31
_diffrn_reflns_theta_max         25.31
_diffrn_reflns_theta_min         1.93
_diffrn_standards_decay_%        9
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.324
_exptl_absorpt_correction_T_max  0.9683
_exptl_absorpt_correction_T_min  0.9090
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.323
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3000
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.1339
_refine_ls_R_factor_gt           0.0686
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0773P)²+1.3256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1565
_refine_ls_wR_factor_ref         0.2058
_reflns_number_gt                1640
_reflns_number_total             3000
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2416.cif
_cod_data_source_block           I
_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 1527 2010-12-29 10:47:43Z saulius 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220477
_cod_database_fobs_code          2220477
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
C C1 0.1724(9) 0.5336(4) 0.9897(12) 0.108(3) Uani d . 1 . .
H H1 0.1202 0.5630 1.0376 0.130 Uiso calc R 1 . .
C C2 0.1344(7) 0.5137(4) 0.8270(9) 0.096(2) Uani d . 1 . .
H H2 0.0583 0.5291 0.7640 0.116 Uiso calc R 1 . .
C C3 0.2149(6) 0.4693(3) 0.7600(7) 0.0610(15) Uani d . 1 . .
C C4 0.3256(5) 0.4465(3) 0.8557(6) 0.0524(13) Uani d . 1 . .
C C5 0.3633(6) 0.4661(3) 1.0209(7) 0.0664(16) Uani d . 1 . .
H H5 0.4376 0.4496 1.0862 0.080 Uiso calc R 1 . .
C C6 0.2832(8) 0.5121(4) 1.0827(9) 0.085(2) Uani d . 1 . .
H H6 0.3064 0.5284 1.1911 0.102 Uiso calc R 1 . .
C C7 0.2792(4) 0.4036(3) 0.5708(6) 0.0456(12) Uani d . 1 . .
C C8 0.2677(5) 0.3692(3) 0.4050(6) 0.0457(12) Uani d . 1 . .
C C9 0.1489(5) 0.3646(3) 0.3069(7) 0.0586(15) Uani d . 1 . .
H H9 0.0800 0.3835 0.3453 0.070 Uiso calc R 1 . .
C C10 0.1297(6) 0.3325(3) 0.1532(8) 0.0712(18) Uani d . 1 . .
H H10 0.0485 0.3300 0.0897 0.085 Uiso calc R 1 . .
C C11 0.2287(6) 0.3044(3) 0.0938(8) 0.0702(17) Uani d . 1 . .
H H11 0.2159 0.2832 -0.0102 0.084 Uiso calc R 1 . .
C C12 0.3461(6) 0.3079(3) 0.1882(8) 0.0664(16) Uani d . 1 . .
H H12 0.4133 0.2888 0.1464 0.080 Uiso calc R 1 . .
C C13 0.3715(5) 0.3394(3) 0.3479(6) 0.0474(12) Uani d . 1 . .
C C14 0.5036(5) 0.3402(3) 0.4373(6) 0.0486(13) Uani d . 1 . .
C C15 0.6821(5) 0.3021(3) 0.5897(6) 0.0478(13) Uani d . 1 . .
C C16 0.7649(6) 0.2577(3) 0.6947(8) 0.0701(17) Uani d . 1 . .
H H16 0.7366 0.2153 0.7297 0.084 Uiso calc R 1 . .
C C17 0.8887(6) 0.2782(4) 0.7449(8) 0.0744(18) Uani d . 1 . .
H H17 0.9447 0.2498 0.8157 0.089 Uiso calc R 1 . .
C C18 0.9307(6) 0.3412(4) 0.6907(7) 0.0682(17) Uani d . 1 . .
H H18 1.0155 0.3532 0.7240 0.082 Uiso calc R 1 . .
C C19 0.8532(5) 0.3858(3) 0.5915(7) 0.0590(15) Uani d . 1 . .
H H19 0.8835 0.4280 0.5583 0.071 Uiso calc R 1 . .
C C20 0.7256(4) 0.3666(3) 0.5396(6) 0.0470(12) Uani d . 1 . .
N N1 0.1893(4) 0.4454(2) 0.5978(5) 0.0545(12) Uani d . 1 . .
N N2 0.5565(4) 0.2888(2) 0.5286(5) 0.0538(11) Uani d . 1 . .
S S1 0.40034(14) 0.39075(8) 0.73836(18) 0.0629(5) Uani d . 1 . .
S S2 0.60337(13) 0.40998(7) 0.41671(19) 0.0594(5) Uani d . 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'
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
C6 C1 C2 . . 122.1(7) ?
C6 C1 H1 . . 118.9 ?
C2 C1 H1 . . 118.9 ?
C1 C2 C3 . . 117.2(7) ?
C1 C2 H2 . . 121.4 ?
C3 C2 H2 . . 121.4 ?
C4 C3 N1 . . 116.0(5) ?
C4 C3 C2 . . 120.4(6) ?
N1 C3 C2 . . 123.6(6) ?
C3 C4 C5 . . 122.3(6) ?
C3 C4 S1 . . 108.9(4) ?
C5 C4 S1 . . 128.8(5) ?
C4 C5 C6 . . 115.9(6) ?
C4 C5 H5 . . 122.0 ?
C6 C5 H5 . . 122.0 ?
C1 C6 C5 . . 121.9(7) ?
C1 C6 H6 . . 119.0 ?
C5 C6 H6 . . 119.0 ?
N1 C7 C8 . . 119.1(4) ?
N1 C7 S1 . . 115.2(4) ?
C8 C7 S1 . . 125.6(4) ?
C9 C8 C13 . . 119.0(5) ?
C9 C8 C7 . . 117.9(4) ?
C13 C8 C7 . . 123.0(4) ?
C8 C9 C10 . . 121.6(5) ?
C8 C9 H9 . . 119.2 ?
C10 C9 H9 . . 119.2 ?
C11 C10 C9 . . 120.5(6) ?
C11 C10 H10 . . 119.7 ?
C9 C10 H10 . . 119.7 ?
C12 C11 C10 . . 119.0(6) ?
C12 C11 H11 . . 120.5 ?
C10 C11 H11 . . 120.5 ?
C11 C12 C13 . . 123.1(6) ?
C11 C12 H12 . . 118.4 ?
C13 C12 H12 . . 118.4 ?
C8 C13 C12 . . 116.7(5) ?
C8 C13 C14 . . 125.5(5) ?
C12 C13 C14 . . 117.8(5) ?
N2 C14 C13 . . 123.7(5) ?
N2 C14 S2 . . 115.2(4) ?
C13 C14 S2 . . 121.0(4) ?
N2 C15 C16 . . 125.4(5) ?
N2 C15 C20 . . 114.4(4) ?
C16 C15 C20 . . 120.2(5) ?
C17 C16 C15 . . 118.5(6) ?
C17 C16 H16 . . 120.7 ?
C15 C16 H16 . . 120.7 ?
C16 C17 C18 . . 120.5(6) ?
C16 C17 H17 . . 119.8 ?
C18 C17 H17 . . 119.8 ?
C19 C18 C17 . . 122.6(6) ?
C19 C18 H18 . . 118.7 ?
C17 C18 H18 . . 118.7 ?
C18 C19 C20 . . 118.2(6) ?
C18 C19 H19 . . 120.9 ?
C20 C19 H19 . . 120.9 ?
C19 C20 C15 . . 119.9(5) ?
C19 C20 S2 . . 130.4(4) ?
C15 C20 S2 . . 109.7(4) ?
C7 N1 C3 . . 110.2(4) ?
C14 N2 C15 . . 111.4(4) ?
C7 S1 C4 . . 89.6(3) ?
C20 S2 C14 . . 89.4(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
C1 C6 . 1.352(10) ?
C1 C2 . 1.372(10) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.395(8) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.369(7) ?
C3 N1 . 1.383(7) ?
C4 C5 . 1.389(7) ?
C4 S1 . 1.730(5) ?
C5 C6 . 1.391(9) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 N1 . 1.305(6) ?
C7 C8 . 1.492(7) ?
C7 S1 . 1.723(5) ?
C8 C9 . 1.379(7) ?
C8 C13 . 1.409(7) ?
C9 C10 . 1.381(8) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.360(8) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.352(8) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.418(7) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.471(7) ?
C14 N2 . 1.301(6) ?
C14 S2 . 1.740(5) ?
C15 N2 . 1.373(6) ?
C15 C16 . 1.402(7) ?
C15 C20 . 1.409(7) ?
C16 C17 . 1.374(8) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.390(9) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.352(8) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.407(7) ?
C19 H19 . 0.9300 ?
C20 S2 . 1.712(5) ?
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
C12 H12 N2 4_565 0.93 2.46 3.370(7) 165.2
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13568040
