#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/52/2225226.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_2225226
loop_
_publ_author_name
'Potgieter, Kim'
'Mayer, Peter'
'Hosten, Eric'
'Gerber, Thomas I. A.'
_publ_section_title
;
 2-[5-(Benzo[d]thiazol-2-yl)thiophen-2-yl]benzo[d]thiazole
;
_journal_coeditor_code           EZ2199
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o531
_journal_paper_doi               10.1107/S1600536810004009
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H10 N2 S3'
_chemical_formula_moiety         'C18 H10 N2 S3'
_chemical_formula_sum            'C18 H10 N2 S3'
_chemical_formula_weight         350.483
_chemical_name_systematic
;
2-[5-(Benzo[d]thiazol-2-yl)thiophen-2-yl]benzo[d]thiazole
;
_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
_audit_block_code                C18H10N2S3_no136_gerber
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_cell_angle_alpha                90.00
_cell_angle_beta                 112.872(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.7297(14)
_cell_length_b                   8.2396(5)
_cell_length_c                   12.8160(12)
_cell_measurement_reflns_used    1275
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.2369
_cell_measurement_theta_min      4.1953
_cell_volume                     1530.4(3)
_computing_cell_refinement
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material
'publCIF (Westrip, 2010) and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Oxford XCalibur'
_diffrn_measurement_method       'omega scans'
_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  0.0526
_diffrn_reflns_av_sigmaI/netI    0.1601
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5789
_diffrn_reflns_theta_full        26.31
_diffrn_reflns_theta_max         26.31
_diffrn_reflns_theta_min         4.20
_exptl_absorpt_coefficient_mu    0.483
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.5212(2)
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.303
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.720
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3086
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.720
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0425
_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)+(0.0060P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0447
_refine_ls_wR_factor_ref         0.0513
_reflns_number_gt                1452
_reflns_number_total             3086
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ez2199.cif
_cod_data_source_block           I
_cod_original_cell_volume        1530.4(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225226
_cod_database_fobs_code          2225226
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 0.19188(5) -0.01268(9) 0.55789(7) 0.0372(2) Uani d . 1 . .
S S2 0.40390(5) 0.14749(8) 0.43819(7) 0.0294(2) Uani d . 1 . .
S S3 0.65397(5) 0.41064(8) 0.64495(7) 0.0351(2) Uani d . 1 . .
N N1 0.22730(15) -0.0478(2) 0.3780(2) 0.0306(7) Uani d . 1 . .
N N2 0.57525(15) 0.3239(2) 0.4337(2) 0.0258(6) Uani d . 1 . .
C C1 0.11335(19) -0.1200(3) 0.4461(3) 0.0294(8) Uani d . 1 . .
C C2 0.1446(2) -0.1266(3) 0.3573(3) 0.0299(8) Uani d . 1 . .
C C3 0.0918(2) -0.2090(3) 0.2584(3) 0.0393(9) Uani d . 1 . .
H H3 0.1119 -0.2156 0.1975 0.047 Uiso calc R 1 . .
C C4 0.0108(2) -0.2802(3) 0.2499(3) 0.0421(9) Uani d . 1 . .
H H4 -0.0250 -0.3369 0.1825 0.051 Uiso calc R 1 . .
C C5 -0.0200(2) -0.2717(3) 0.3369(3) 0.0436(9) Uani d . 1 . .
H H5 -0.0766 -0.3220 0.3284 0.052 Uiso calc R 1 . .
C C6 0.0300(2) -0.1917(3) 0.4350(3) 0.0383(9) Uani d . 1 . .
H H6 0.0084 -0.1851 0.4946 0.046 Uiso calc R 1 . .
C C7 0.25959(18) 0.0157(3) 0.4775(3) 0.0252(7) Uani d . 1 . .
C C8 0.34453(18) 0.1056(3) 0.5237(3) 0.0233(7) Uani d . 1 . .
C C9 0.38812(19) 0.1676(3) 0.6290(3) 0.0321(8) Uani d . 1 . .
H H9 0.3656 0.1568 0.6875 0.039 Uiso calc R 1 . .
C C10 0.46999(19) 0.2493(3) 0.6426(2) 0.0292(8) Uani d . 1 . .
H H10 0.5091 0.2988 0.7115 0.035 Uiso calc R 1 . .
C C11 0.48737(18) 0.2503(3) 0.5468(2) 0.0242(7) Uani d . 1 . .
C C12 0.56531(19) 0.3212(3) 0.5304(3) 0.0252(8) Uani d . 1 . .
C C13 0.70982(19) 0.4587(3) 0.5569(3) 0.0278(8) Uani d . 1 . .
C C14 0.6576(2) 0.4025(3) 0.4477(3) 0.0280(8) Uani d . 1 . .
C C15 0.6891(2) 0.4295(3) 0.3612(3) 0.0372(8) Uani d . 1 . .
H H15 0.6546 0.3929 0.2862 0.045 Uiso calc R 1 . .
C C16 0.7711(2) 0.5105(3) 0.3873(3) 0.0401(9) Uani d . 1 . .
H H16 0.7925 0.5313 0.3287 0.048 Uiso calc R 1 . .
C C17 0.8235(2) 0.5627(3) 0.4957(3) 0.0392(9) Uani d . 1 . .
H H17 0.8806 0.6163 0.5109 0.047 Uiso calc R 1 . .
C C18 0.79350(19) 0.5377(3) 0.5819(3) 0.0370(9) Uani d . 1 . .
H H18 0.8291 0.5735 0.6567 0.044 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?
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
C1 S1 C7 . . 89.01(14) ?
C11 S2 C8 . . 90.91(14) ?
C13 S3 C12 . . 89.42(14) ?
C7 N1 C2 . . 111.1(3) ?
C12 N2 C14 . . 109.4(2) ?
C6 C1 C2 . . 120.8(3) ?
C6 C1 S1 . . 129.9(3) ?
C2 C1 S1 . . 109.2(2) ?
N1 C2 C3 . . 125.9(3) ?
N1 C2 C1 . . 115.2(3) ?
C3 C2 C1 . . 118.9(3) ?
C4 C3 C2 . . 119.3(3) ?
C4 C3 H3 . . 120.4 ?
C2 C3 H3 . . 120.4 ?
C3 C4 C5 . . 121.5(3) ?
C3 C4 H4 . . 119.3 ?
C5 C4 H4 . . 119.3 ?
C6 C5 C4 . . 120.8(3) ?
C6 C5 H5 . . 119.6 ?
C4 C5 H5 . . 119.6 ?
C5 C6 C1 . . 118.6(3) ?
C5 C6 H6 . . 120.7 ?
C1 C6 H6 . . 120.7 ?
N1 C7 C8 . . 124.3(3) ?
N1 C7 S1 . . 115.5(2) ?
C8 C7 S1 . . 120.2(2) ?
C9 C8 C7 . . 129.4(3) ?
C9 C8 S2 . . 111.5(2) ?
C7 C8 S2 . . 119.1(2) ?
C8 C9 C10 . . 113.0(3) ?
C8 C9 H9 . . 123.5 ?
C10 C9 H9 . . 123.5 ?
C11 C10 C9 . . 112.8(3) ?
C11 C10 H10 . . 123.6 ?
C9 C10 H10 . . 123.6 ?
C10 C11 C12 . . 127.9(3) ?
C10 C11 S2 . . 111.7(2) ?
C12 C11 S2 . . 120.3(2) ?
N2 C12 C11 . . 124.4(3) ?
N2 C12 S3 . . 116.0(2) ?
C11 C12 S3 . . 119.5(2) ?
C18 C13 C14 . . 121.4(3) ?
C18 C13 S3 . . 129.3(3) ?
C14 C13 S3 . . 109.2(2) ?
C15 C14 N2 . . 124.7(3) ?
C15 C14 C13 . . 119.4(3) ?
N2 C14 C13 . . 115.9(3) ?
C16 C15 C14 . . 118.3(3) ?
C16 C15 H15 . . 120.9 ?
C14 C15 H15 . . 120.9 ?
C15 C16 C17 . . 122.2(3) ?
C15 C16 H16 . . 118.9 ?
C17 C16 H16 . . 118.9 ?
C18 C17 C16 . . 120.3(3) ?
C18 C17 H17 . . 119.8 ?
C16 C17 H17 . . 119.8 ?
C17 C18 C13 . . 118.3(3) ?
C17 C18 H18 . . 120.8 ?
C13 C18 H18 . . 120.8 ?
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 . 1.728(3) ?
S1 C7 . 1.761(3) ?
S2 C11 . 1.720(3) ?
S2 C8 . 1.729(3) ?
S3 C13 . 1.725(3) ?
S3 C12 . 1.747(3) ?
N1 C7 . 1.286(3) ?
N1 C2 . 1.384(3) ?
N2 C12 . 1.308(3) ?
N2 C14 . 1.397(3) ?
C1 C6 . 1.394(3) ?
C1 C2 . 1.404(4) ?
C2 C3 . 1.392(3) ?
C3 C4 . 1.368(4) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.379(4) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.366(4) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C8 . 1.438(3) ?
C8 C9 . 1.353(3) ?
C9 C10 . 1.403(3) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.357(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.445(3) ?
C13 C18 . 1.389(3) ?
C13 C14 . 1.398(4) ?
C14 C15 . 1.396(4) ?
C15 C16 . 1.374(3) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.380(4) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.375(4) ?
C17 H17 . 0.9500 ?
C18 H18 . 0.9500 ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
? ? ? ? ? ?
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
_geom_hbond_publ_flag
C16 H16 N1 2_655 0.95 2.63 3.444(4) 144.4 yes
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 S1 C1 C6 . . . . -178.8(3) ?
C7 S1 C1 C2 . . . . 0.3(2) ?
C7 N1 C2 C3 . . . . -179.5(3) ?
C7 N1 C2 C1 . . . . 0.5(3) ?
C6 C1 C2 N1 . . . . 178.7(2) ?
S1 C1 C2 N1 . . . . -0.5(3) ?
C6 C1 C2 C3 . . . . -1.3(4) ?
S1 C1 C2 C3 . . . . 179.5(2) ?
N1 C2 C3 C4 . . . . -179.5(3) ?
C1 C2 C3 C4 . . . . 0.5(4) ?
C2 C3 C4 C5 . . . . 0.3(5) ?
C3 C4 C5 C6 . . . . -0.3(5) ?
C4 C5 C6 C1 . . . . -0.6(5) ?
C2 C1 C6 C5 . . . . 1.4(4) ?
S1 C1 C6 C5 . . . . -179.6(2) ?
C2 N1 C7 C8 . . . . -180.0(2) ?
C2 N1 C7 S1 . . . . -0.3(3) ?
C1 S1 C7 N1 . . . . 0.0(2) ?
C1 S1 C7 C8 . . . . 179.7(2) ?
N1 C7 C8 C9 . . . . -174.9(3) ?
S1 C7 C8 C9 . . . . 5.4(4) ?
N1 C7 C8 S2 . . . . 5.6(4) ?
S1 C7 C8 S2 . . . . -174.02(14) ?
C11 S2 C8 C9 . . . . -0.3(2) ?
C11 S2 C8 C7 . . . . 179.2(2) ?
C7 C8 C9 C10 . . . . -179.6(2) ?
S2 C8 C9 C10 . . . . -0.1(3) ?
C8 C9 C10 C11 . . . . 0.7(4) ?
C9 C10 C11 C12 . . . . -179.3(2) ?
C9 C10 C11 S2 . . . . -0.9(3) ?
C8 S2 C11 C10 . . . . 0.7(2) ?
C8 S2 C11 C12 . . . . 179.2(2) ?
C14 N2 C12 C11 . . . . 179.5(2) ?
C14 N2 C12 S3 . . . . -0.6(3) ?
C10 C11 C12 N2 . . . . -176.7(3) ?
S2 C11 C12 N2 . . . . 5.1(4) ?
C10 C11 C12 S3 . . . . 3.4(4) ?
S2 C11 C12 S3 . . . . -174.81(13) ?
C13 S3 C12 N2 . . . . 0.6(2) ?
C13 S3 C12 C11 . . . . -179.5(2) ?
C12 S3 C13 C18 . . . . -179.6(3) ?
C12 S3 C13 C14 . . . . -0.4(2) ?
C12 N2 C14 C15 . . . . -178.8(3) ?
C12 N2 C14 C13 . . . . 0.2(3) ?
C18 C13 C14 C15 . . . . -1.5(4) ?
S3 C13 C14 C15 . . . . 179.3(2) ?
C18 C13 C14 N2 . . . . 179.4(2) ?
S3 C13 C14 N2 . . . . 0.2(3) ?
N2 C14 C15 C16 . . . . 179.2(2) ?
C13 C14 C15 C16 . . . . 0.3(4) ?
C14 C15 C16 C17 . . . . 1.2(4) ?
C15 C16 C17 C18 . . . . -1.4(5) ?
C16 C17 C18 C13 . . . . 0.1(4) ?
C14 C13 C18 C17 . . . . 1.3(4) ?
S3 C13 C18 C17 . . . . -179.7(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2906006
