##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
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data_I
_audit_creation_method     SHELXL-2013
_journal_date_recd_electronic     2016-05-04
_journal_date_accepted     2016-08-10
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2016
_journal_volume     72
_journal_issue      9
_journal_page_first     679
_journal_page_last     684
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229616012973
_journal_coeditor_code     EG3204
_publ_contact_author_name     'Weber, Edwin'
_publ_contact_author_address
;
Institut für Organische Chemie
TU Bergakademie Freiberg
Leipziger Strasse 29
D-09596 Freiberg/Sachsen
Germany
;
_publ_contact_author_email     edwin.weber@chemie.tu-freiberg.de
_publ_contact_author_fax     '+49(0)3731 393170'
_publ_contact_author_phone     '+49(0)3731 392386'
_publ_section_title
;
Crystal structures of functional building blocks derived from
bis(benzo[b]thiophen-2-yl)methane
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Katzsch, Felix' .
;
Institut für Organische Chemie
TU Bergakademie Freiberg
Leipziger Strasse 29
D-09596 Freiberg/Sachsen
Germany
;
    'Gruber, Tobias' .
;
School of Pharmacy
University of Lincoln
Joseph Banks Laboratories
Green Lane
Lincoln LN6 7DL
England
;
    'Weber, Edwin' .
;
Institut für Organische Chemie
TU Bergakademie Freiberg
Leipziger Strasse 29
D-09596 Freiberg/Sachsen
Germany
;
_publ_section_synopsis
;
The syntheses of three bis(benzo[b]thiophen-2-yl)methane derivatives are
described and their crystal structures discussed comparatively. The
conformations of the title compounds compared with respective bioisoteres and
APIs containing the dithien-2-ylmethane scaffold.
;
_database_code_depnum_ccdc_archive     'CCDC 1498663'
_chemical_name_systematic
;
Bis(benzo[b]thiophen-2-yl)methanone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H10 O S2'
_chemical_formula_sum     'C17 H10 O S2'
_chemical_formula_iupac     'C17 H10 O S2'
_chemical_formula_weight     294.37
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'A b a 2'
_space_group_name_Hall     'A 2 -2ac'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, z'
    'x+1/2, -y+1/2, z'
    '-x+1/2, y+1/2, z'
    'x, y+1/2, z+1/2'
    '-x, -y+1/2, z+1/2'
    'x+1/2, -y+1, z+1/2'
    '-x+1/2, y+1, z+1/2'
_cell_length_a     18.2186(4)
_cell_length_b     20.0166(4)
_cell_length_c     7.2534(2)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     2645.13(11)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     9041
_cell_measurement_theta_min     2.32
_cell_measurement_theta_max     34.97
_cell_measurement_temperature     100(2)
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.350
_exptl_crystal_size_mid     0.340
_exptl_crystal_size_min     0.100
_exptl_crystal_density_diffrn     1.478
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     1216
_exptl_absorpt_coefficient_mu     0.393
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2004)
;
_shelx_estimated_absorpt_T_min     0.875
_shelx_estimated_absorpt_T_max     0.962
_exptl_absorpt_correction_T_min     0.8748
_exptl_absorpt_correction_T_max     0.9618
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type
                      'Bruker Kappa goniometer with an APEXII CCD area detector'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     13345
_diffrn_reflns_av_R_equivalents     0.0267
_diffrn_reflns_theta_min     2.035
_diffrn_reflns_theta_max     24.997
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     0.975
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     21
_diffrn_reflns_limit_k_min     -23
_diffrn_reflns_limit_k_max     23
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_limit_l_max     8
_refine_special_details     ?
_reflns_number_total     2327
_reflns_number_gt     2282
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0259
_refine_ls_R_factor_gt     0.0252
_refine_ls_wR_factor_gt     0.0668
_refine_ls_wR_factor_ref     0.0671
_refine_ls_goodness_of_fit_ref     0.992
_refine_ls_restrained_S_all     0.992
_refine_ls_number_reflns     2327
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0377P)²+3.9183P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.422
_refine_diff_density_min     -0.276
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x determined using 1027 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons & Flack, 2004)
;
_refine_ls_abs_structure_Flack     0.03(2)
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'
    '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'
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_cell_refinement
;
SAINT-NT (Bruker, 2008)
;
_computing_data_reduction
;
SAINT-NT (Bruker, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.75309(12) 0.69981(10) 1.0553(3) 0.0223(5) Uani d 1 . .
    S S1 0.76808(4) 0.55431(4) 1.10846(11) 0.01741(19) Uani d 1 . .
    S S2 0.84820(4) 0.80488(3) 0.88387(12) 0.01572(18) Uani d 1 . .
    C C1 0.82947(16) 0.60759(14) 0.9991(4) 0.0131(6) Uani d 1 . .
    C C2 0.88343(17) 0.57534(13) 0.8931(4) 0.0153(6) Uani d 1 . .
    H H2 0.9214 0.5970 0.8259 0.018 Uiso calc 1 . .
    C C3 0.87191(15) 0.50314(15) 0.9026(4) 0.0141(6) Uani d 1 . .
    C C4 0.91093(16) 0.45231(15) 0.8115(4) 0.0168(6) Uani d 1 . .
    H H4 0.9511 0.4632 0.7335 0.020 Uiso calc 1 . .
    C C5 0.89051(16) 0.38673(15) 0.8364(4) 0.0173(7) Uani d 1 . .
    H H5 0.9171 0.3523 0.7759 0.021 Uiso calc 1 . .
    C C6 0.83086(17) 0.37018(15) 0.9502(4) 0.0170(6) Uani d 1 . .
    H H6 0.8175 0.3246 0.9653 0.020 Uiso calc 1 . .
    C C7 0.79150(16) 0.41898(15) 1.0403(4) 0.0161(6) Uani d 1 . .
    H H7 0.7512 0.4077 1.1172 0.019 Uiso calc 1 . .
    C C8 0.81227(15) 0.48537(14) 1.0158(4) 0.0138(6) Uani d 1 . .
    C C9 0.87383(16) 0.72714(13) 0.9694(4) 0.0129(6) Uani d 1 . .
    C C10 0.94780(16) 0.72143(14) 1.0019(4) 0.0139(6) Uani d 1 . .
    H H10 0.9708 0.6821 1.0472 0.017 Uiso calc 1 . .
    C C11 0.98609(16) 0.78209(14) 0.9592(4) 0.0134(6) Uani d 1 . .
    C C12 1.06093(17) 0.79737(14) 0.9823(4) 0.0152(6) Uani d 1 . .
    H H12 1.0937 0.7651 1.0316 0.018 Uiso calc 1 . .
    C C13 1.08617(17) 0.85968(15) 0.9327(4) 0.0170(7) Uani d 1 . .
    H H13 1.1366 0.8703 0.9493 0.020 Uiso calc 1 . .
    C C14 1.03856(18) 0.90768(15) 0.8579(4) 0.0186(7) Uani d 1 . .
    H H14 1.0574 0.9500 0.8224 0.022 Uiso calc 1 . .
    C C15 0.96454(17) 0.89438(15) 0.8351(4) 0.0161(6) Uani d 1 . .
    H H15 0.9324 0.9269 0.7844 0.019 Uiso calc 1 . .
    C C16 0.93852(15) 0.83169(14) 0.8887(4) 0.0136(6) Uani d 1 . .
    C C17 0.81376(16) 0.67971(15) 1.0119(4) 0.0145(6) Uani d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    O1 C17 . 1.217(4) ?
    S1 C8 . 1.733(3) ?
    S1 C1 . 1.737(3) ?
    S2 C16 . 1.731(3) ?
    S2 C9 . 1.739(3) ?
    C1 C2 . 1.405(4) ?
    C1 C17 . 1.475(4) ?
    C2 C3 . 1.462(4) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.406(4) ?
    C3 C8 . 1.408(4) ?
    C4 C5 . 1.376(4) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.405(4) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.376(4) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.393(4) ?
    C7 H7 . 0.9500 ?
    C9 C10 . 1.373(4) ?
    C9 C17 . 1.481(4) ?
    C10 C11 . 1.434(4) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.407(4) ?
    C11 C16 . 1.414(4) ?
    C12 C13 . 1.377(4) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.404(4) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.384(4) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.397(4) ?
    C15 H15 . 0.9500 ?
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 C1 . . 90.71(14) ?
    C16 S2 C9 . . 90.85(14) ?
    C2 C1 C17 . . 128.3(3) ?
    C2 C1 S1 . . 114.7(2) ?
    C17 C1 S1 . . 116.6(2) ?
    C1 C2 C3 . . 109.1(3) ?
    C1 C2 H2 . . 125.4 ?
    C3 C2 H2 . . 125.4 ?
    C4 C3 C8 . . 118.8(3) ?
    C4 C3 C2 . . 128.4(3) ?
    C8 C3 C2 . . 112.8(3) ?
    C5 C4 C3 . . 119.5(3) ?
    C5 C4 H4 . . 120.3 ?
    C3 C4 H4 . . 120.3 ?
    C4 C5 C6 . . 120.7(3) ?
    C4 C5 H5 . . 119.6 ?
    C6 C5 H5 . . 119.6 ?
    C7 C6 C5 . . 121.0(3) ?
    C7 C6 H6 . . 119.5 ?
    C5 C6 H6 . . 119.5 ?
    C6 C7 C8 . . 118.4(3) ?
    C6 C7 H7 . . 120.8 ?
    C8 C7 H7 . . 120.8 ?
    C7 C8 C3 . . 121.7(3) ?
    C7 C8 S1 . . 125.7(2) ?
    C3 C8 S1 . . 112.6(2) ?
    C10 C9 C17 . . 129.5(3) ?
    C10 C9 S2 . . 113.5(2) ?
    C17 C9 S2 . . 116.7(2) ?
    C9 C10 C11 . . 111.7(3) ?
    C9 C10 H10 . . 124.1 ?
    C11 C10 H10 . . 124.1 ?
    C12 C11 C16 . . 119.0(3) ?
    C12 C11 C10 . . 129.0(3) ?
    C16 C11 C10 . . 112.0(3) ?
    C13 C12 C11 . . 119.3(3) ?
    C13 C12 H12 . . 120.4 ?
    C11 C12 H12 . . 120.4 ?
    C12 C13 C14 . . 121.0(3) ?
    C12 C13 H13 . . 119.5 ?
    C14 C13 H13 . . 119.5 ?
    C15 C14 C13 . . 121.1(3) ?
    C15 C14 H14 . . 119.5 ?
    C13 C14 H14 . . 119.5 ?
    C14 C15 C16 . . 118.0(3) ?
    C14 C15 H15 . . 121.0 ?
    C16 C15 H15 . . 121.0 ?
    C15 C16 C11 . . 121.6(3) ?
    C15 C16 S2 . . 126.5(2) ?
    C11 C16 S2 . . 111.9(2) ?
    O1 C17 C1 . . 121.1(3) ?
    O1 C17 C9 . . 120.8(3) ?
    C1 C17 C9 . . 118.1(3) ?
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
    C8 S1 C1 C2 . . . . -0.1(2) ?
    C8 S1 C1 C17 . . . . 173.4(2) ?
    C17 C1 C2 C3 . . . . -171.8(3) ?
    S1 C1 C2 C3 . . . . 0.8(3) ?
    C1 C2 C3 C4 . . . . 177.0(3) ?
    C1 C2 C3 C8 . . . . -1.3(3) ?
    C8 C3 C4 C5 . . . . -0.6(4) ?
    C2 C3 C4 C5 . . . . -178.8(3) ?
    C3 C4 C5 C6 . . . . 0.5(5) ?
    C4 C5 C6 C7 . . . . -0.2(5) ?
    C5 C6 C7 C8 . . . . 0.0(4) ?
    C6 C7 C8 C3 . . . . -0.1(4) ?
    C6 C7 C8 S1 . . . . 177.2(2) ?
    C4 C3 C8 C7 . . . . 0.4(4) ?
    C2 C3 C8 C7 . . . . 178.9(3) ?
    C4 C3 C8 S1 . . . . -177.3(2) ?
    C2 C3 C8 S1 . . . . 1.2(3) ?
    C1 S1 C8 C7 . . . . -178.2(3) ?
    C1 S1 C8 C3 . . . . -0.6(2) ?
    C16 S2 C9 C10 . . . . 0.4(2) ?
    C16 S2 C9 C17 . . . . 175.1(2) ?
    C17 C9 C10 C11 . . . . -173.1(3) ?
    S2 C9 C10 C11 . . . . 0.8(3) ?
    C9 C10 C11 C12 . . . . 176.5(3) ?
    C9 C10 C11 C16 . . . . -2.0(4) ?
    C16 C11 C12 C13 . . . . -1.2(4) ?
    C10 C11 C12 C13 . . . . -179.5(3) ?
    C11 C12 C13 C14 . . . . -0.7(4) ?
    C12 C13 C14 C15 . . . . 1.3(5) ?
    C13 C14 C15 C16 . . . . 0.0(4) ?
    C14 C15 C16 C11 . . . . -1.9(4) ?
    C14 C15 C16 S2 . . . . 176.8(3) ?
    C12 C11 C16 C15 . . . . 2.5(4) ?
    C10 C11 C16 C15 . . . . -178.9(3) ?
    C12 C11 C16 S2 . . . . -176.4(2) ?
    C10 C11 C16 S2 . . . . 2.3(3) ?
    C9 S2 C16 C15 . . . . 179.7(3) ?
    C9 S2 C16 C11 . . . . -1.5(2) ?
    C2 C1 C17 O1 . . . . 154.8(3) ?
    S1 C1 C17 O1 . . . . -17.6(4) ?
    C2 C1 C17 C9 . . . . -24.8(4) ?
    S1 C1 C17 C9 . . . . 162.8(2) ?
    C10 C9 C17 O1 . . . . 145.8(3) ?
    S2 C9 C17 O1 . . . . -27.9(4) ?
    C10 C9 C17 C1 . . . . -34.5(5) ?
    S2 C9 C17 C1 . . . . 151.7(2) ?
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
    C13 H13 O1 3_565 0.95 2.66 3.385(3) 133.6
    C5 H5 Cg4 5_544 0.95 2.90 3.694(11) 142.0
    C10 H10 Cg2 6_765 0.95 2.70 3.324(12) 123.7
data_II
_audit_creation_method     'SHELXL-2014/7'
_journal_date_recd_electronic     2016-05-04
_journal_date_accepted     2016-08-10
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2016
_journal_volume     72
_journal_issue      9
_journal_page_first     679
_journal_page_last     684
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229616012973
_journal_coeditor_code     EG3204
_database_code_depnum_ccdc_archive     'CCDC 1498664'
_chemical_name_systematic
;
1,1-Bis(benzo[b]thiophen-2-yl)-3-(trimethylsilyl)prop-2-yn-1-ol
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H20 O S2 Si'
_chemical_formula_sum     'C22 H20 O S2 Si'
_chemical_formula_iupac     'C22 H20 O S2 Si'
_chemical_formula_weight     392.59
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P n m a'
_space_group_name_Hall     '-P 2ac 2n'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z'
    'x+1/2, -y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    'x, -y-1/2, z'
    '-x-1/2, y-1/2, z-1/2'
_cell_length_a     19.3755(5)
_cell_length_b     17.0998(4)
_cell_length_c     5.96560(10)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1976.51(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4265
_cell_measurement_theta_min     2.42
_cell_measurement_theta_max     33.44
_cell_measurement_temperature     100(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.58
_exptl_crystal_size_mid     0.44
_exptl_crystal_size_min     0.19
_exptl_crystal_density_diffrn     1.319
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     824
_exptl_absorpt_coefficient_mu     0.338
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2004)
;
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     0.8279
_exptl_absorpt_correction_T_max     0.9385
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type
                      'Bruker Kappa goniometer with an APEXII CCD area detector'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4278
_diffrn_reflns_av_R_equivalents     0.0160
_diffrn_reflns_theta_min     2.102
_diffrn_reflns_theta_max     27.499
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -24
_diffrn_reflns_limit_h_max     0
_diffrn_reflns_limit_k_min     -22
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     7
_refine_special_details     ?
_reflns_number_total     2345
_reflns_number_gt     1991
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0400
_refine_ls_R_factor_gt     0.0327
_refine_ls_wR_factor_gt     0.0788
_refine_ls_wR_factor_ref     0.0820
_refine_ls_goodness_of_fit_ref     1.062
_refine_ls_restrained_S_all     1.081
_refine_ls_number_reflns     2345
_refine_ls_number_parameters     151
_refine_ls_number_restraints     5
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0349P)²+0.8238P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.305
_refine_diff_density_min     -0.322
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
    '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'
    'Si' 'Si' 0.0817 0.0704
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_cell_refinement
;
SAINT-NT (Bruker, 2008)
;
_computing_data_reduction
;
SAINT-NT (Bruker, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Si Si1 0.49457(2) 0.7500 0.27063(8) 0.02004(13) Uani d 1 . .
    S S1 0.18173(4) 0.64903(5) 0.72862(13) 0.02106(16) Uani d 0.64 A 1
    S S1B 0.25524(8) 0.62932(10) 0.2747(2) 0.0179(3) Uani d 0.36 A 2
    C C1 0.28354(9) 0.7500 0.5884(3) 0.0201(4) Uani d 1 A .
    O O1 0.29528(7) 0.7500 0.8252(2) 0.0271(3) Uani d 1 . .
    H H1 0.3138(19) 0.7922(13) 0.865(6) 0.052(12) Uiso d 0.5 . .
    C C2 0.24199(6) 0.67730(8) 0.5315(2) 0.0181(3) Uani d 1 . .
    C C3 0.24152(18) 0.6339(3) 0.3446(6) 0.0244(8) Uani d 0.64 A 1
    H H3 0.2710 0.6445 0.2212 0.029 Uiso calc 0.64 A 1
    C C3B 0.1927(3) 0.6387(3) 0.6495(8) 0.0258(13) Uani d 0.36 A 2
    H H3B 0.1816 0.6547 0.7976 0.031 Uiso calc 0.36 A 2
    C C4 0.19188(6) 0.56845(8) 0.3441(2) 0.0240(3) Uani d 1 . .
    C C5 0.17515(8) 0.50935(9) 0.1933(3) 0.0316(3) Uani d 1 . .
    H H5 0.1988 0.5052 0.0544 0.038 Uiso calc 1 . .
    C C6 0.12397(9) 0.45706(9) 0.2476(3) 0.0362(4) Uani d 1 . .
    H H6 0.1122 0.4167 0.1452 0.043 Uiso calc 1 . .
    C C7 0.08915(8) 0.46275(9) 0.4518(3) 0.0358(4) Uani d 1 . .
    H H7 0.0537 0.4263 0.4860 0.043 Uiso calc 1 . .
    C C8 0.10537(7) 0.52028(9) 0.6043(3) 0.0284(3) Uani d 1 . .
    H H8 0.0817 0.5237 0.7435 0.034 Uiso calc 1 . .
    C C9 0.15736(7) 0.57358(8) 0.5501(2) 0.0210(3) Uani d 1 . .
    C C10 0.34990(9) 0.7500 0.4663(3) 0.0226(4) Uani d 1 . .
    C C11 0.40588(9) 0.7500 0.3796(3) 0.0210(4) Uani d 1 A .
    C C12 0.49279(11) 0.7500 -0.0405(3) 0.0293(4) Uani d 1 . .
    H H12A 0.4822 0.6972 -0.0946 0.044 Uiso calc 0.5 . .
    H H12B 0.5379 0.7663 -0.0980 0.044 Uiso calc 0.5 . .
    H H12C 0.4573 0.7865 -0.0931 0.044 Uiso calc 0.5 . .
    C C13 0.53701(10) 0.83950(13) 0.3775(3) 0.0549(6) Uani d 1 . .
    H H13A 0.5136 0.8857 0.3168 0.082 Uiso calc 1 . .
    H H13B 0.5855 0.8399 0.3308 0.082 Uiso calc 1 . .
    H H13C 0.5344 0.8403 0.5416 0.082 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    Si1 C11 . 1.8372(19) ?
    Si1 C13 7_575 1.8508(17) ?
    Si1 C13 . 1.8508(17) ?
    Si1 C12 . 1.856(2) ?
    S1 C2 . 1.7263(14) ?
    S1 C9 . 1.7384(15) ?
    S1B C4 . 1.662(2) ?
    S1B C2 . 1.7567(19) ?
    C1 O1 . 1.431(2) ?
    C1 C10 . 1.478(3) ?
    C1 C2 7_575 1.5193(16) ?
    C1 C2 . 1.5194(16) ?
    O1 H1 . 0.839(10) ?
    C2 C3 . 1.339(4) ?
    C2 C3B . 1.358(5) ?
    C3 C4 . 1.476(4) ?
    C3 H3 . 0.9500 ?
    C3B C9 . 1.435(5) ?
    C3B H3B . 0.9500 ?
    C4 C5 . 1.391(2) ?
    C4 C9 . 1.4018(19) ?
    C5 C6 . 1.374(2) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.396(2) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.377(2) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.3965(19) ?
    C8 H8 . 0.9500 ?
    C10 C11 . 1.202(3) ?
    C12 H12A . 0.9800 ?
    C12 H12B . 0.9800 ?
    C12 H12C . 0.9800 ?
    C13 H13A . 0.9800 ?
    C13 H13B . 0.9800 ?
    C13 H13C . 0.9800 ?
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
    C11 Si1 C13 . 7_575 107.08(8) ?
    C11 Si1 C13 . . 107.08(8) ?
    C13 Si1 C13 7_575 . 111.57(15) ?
    C11 Si1 C12 . . 109.66(10) ?
    C13 Si1 C12 7_575 . 110.66(7) ?
    C13 Si1 C12 . . 110.66(7) ?
    C2 S1 C9 . . 88.52(7) ?
    C4 S1B C2 . . 88.13(9) ?
    O1 C1 C10 . . 110.37(15) ?
    O1 C1 C2 . 7_575 107.74(10) ?
    C10 C1 C2 . 7_575 110.54(10) ?
    O1 C1 C2 . . 107.74(10) ?
    C10 C1 C2 . . 110.55(10) ?
    C2 C1 C2 7_575 . 109.82(14) ?
    C1 O1 H1 . . 110(3) ?
    C3 C2 C1 . . 130.00(19) ?
    C3B C2 C1 . . 130.9(2) ?
    C3 C2 S1 . . 114.04(17) ?
    C1 C2 S1 . . 115.81(10) ?
    C3B C2 S1B . . 109.1(2) ?
    C1 C2 S1B . . 119.97(11) ?
    C2 C3 C4 . . 115.2(2) ?
    C2 C3 H3 . . 122.4 ?
    C4 C3 H3 . . 122.4 ?
    C2 C3B C9 . . 119.9(4) ?
    C2 C3B H3B . . 120.0 ?
    C9 C3B H3B . . 120.0 ?
    C5 C4 C9 . . 120.08(13) ?
    C5 C4 C3 . . 134.76(17) ?
    C9 C4 C3 . . 105.16(17) ?
    C5 C4 S1B . . 117.77(12) ?
    C9 C4 S1B . . 122.12(12) ?
    C6 C5 C4 . . 119.22(14) ?
    C6 C5 H5 . . 120.4 ?
    C4 C5 H5 . . 120.4 ?
    C5 C6 C7 . . 120.62(14) ?
    C5 C6 H6 . . 119.7 ?
    C7 C6 H6 . . 119.7 ?
    C8 C7 C6 . . 121.10(14) ?
    C8 C7 H7 . . 119.4 ?
    C6 C7 H7 . . 119.4 ?
    C7 C8 C9 . . 118.54(14) ?
    C7 C8 H8 . . 120.7 ?
    C9 C8 H8 . . 120.7 ?
    C8 C9 C4 . . 120.43(13) ?
    C8 C9 C3B . . 139.0(2) ?
    C4 C9 C3B . . 100.6(2) ?
    C8 C9 S1 . . 122.57(11) ?
    C4 C9 S1 . . 116.99(11) ?
    C11 C10 C1 . . 176.0(2) ?
    C10 C11 Si1 . . 175.22(18) ?
    Si1 C12 H12A . . 109.5 ?
    Si1 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    Si1 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    Si1 C13 H13A . . 109.5 ?
    Si1 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    Si1 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
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
    O1 C1 C2 C3 . . . . -149.3(3) ?
    C10 C1 C2 C3 . . . . -28.6(3) ?
    C2 C1 C2 C3 7_575 . . . 93.6(3) ?
    O1 C1 C2 C3B . . . . 33.6(4) ?
    C10 C1 C2 C3B . . . . 154.3(3) ?
    C2 C1 C2 C3B 7_575 . . . -83.5(4) ?
    O1 C1 C2 S1 . . . . 35.55(14) ?
    C10 C1 C2 S1 . . . . 156.23(11) ?
    C2 C1 C2 S1 7_575 . . . -81.53(15) ?
    O1 C1 C2 S1B . . . . -146.19(12) ?
    C10 C1 C2 S1B . . . . -25.51(17) ?
    C2 C1 C2 S1B 7_575 . . . 96.73(15) ?
    C9 S1 C2 C3 . . . . 1.7(2) ?
    C9 S1 C2 C1 . . . . 177.66(10) ?
    C4 S1B C2 C3B . . . . 3.4(3) ?
    C4 S1B C2 C1 . . . . -176.76(11) ?
    C1 C2 C3 C4 . . . . -177.48(16) ?
    S1 C2 C3 C4 . . . . -2.2(3) ?
    C1 C2 C3B C9 . . . . 175.6(2) ?
    S1B C2 C3B C9 . . . . -4.6(5) ?
    C2 C3 C4 C5 . . . . -178.47(17) ?
    C2 C3 C4 C9 . . . . 1.5(3) ?
    C2 S1B C4 C5 . . . . -179.69(11) ?
    C2 S1B C4 C9 . . . . -1.93(15) ?
    C9 C4 C5 C6 . . . . 0.9(2) ?
    C3 C4 C5 C6 . . . . -179.2(3) ?
    S1B C4 C5 C6 . . . . 178.67(13) ?
    C4 C5 C6 C7 . . . . -0.2(2) ?
    C5 C6 C7 C8 . . . . -0.5(2) ?
    C6 C7 C8 C9 . . . . 0.4(2) ?
    C7 C8 C9 C4 . . . . 0.2(2) ?
    C7 C8 C9 C3B . . . . -177.5(4) ?
    C7 C8 C9 S1 . . . . 179.50(12) ?
    C5 C4 C9 C8 . . . . -0.89(19) ?
    C3 C4 C9 C8 . . . . 179.1(2) ?
    S1B C4 C9 C8 . . . . -178.61(13) ?
    C5 C4 C9 C3B . . . . 177.6(3) ?
    S1B C4 C9 C3B . . . . -0.1(3) ?
    C5 C4 C9 S1 . . . . 179.80(11) ?
    C3 C4 C9 S1 . . . . -0.2(2) ?
    C2 C3B C9 C8 . . . . -178.9(2) ?
    C2 C3B C9 C4 . . . . 3.1(5) ?
    C2 S1 C9 C8 . . . . 179.90(12) ?
    C2 S1 C9 C4 . . . . -0.82(11) ?
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
    O1 H1 S1B 7_576 0.839(10) 3.01(4) 3.4717(19) 117(3)
    C5 H5 S1B 2_564 0.95 2.98 3.698(2) 133.7
data_III
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2016-05-04
_journal_date_accepted     2016-08-10
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2016
_journal_volume     72
_journal_issue      9
_journal_page_first     679
_journal_page_last     684
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229616012973
_journal_coeditor_code     EG3204
_database_code_depnum_ccdc_archive     'CCDC 1498665'
_chemical_name_systematic
;
1,1-Bis(benzo[b]thiophen-2-yl)prop-2-yn-1-ol
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H12 O S2'
_chemical_formula_sum     'C19 H12 O S2'
_chemical_formula_iupac     'C19 H12 O S2'
_chemical_formula_weight     320.41
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     9.4426(3)
_cell_length_b     19.5197(6)
_cell_length_c     8.4323(3)
_cell_angle_alpha     90.00
_cell_angle_beta     101.539(2)
_cell_angle_gamma     90.00
_cell_volume     1522.80(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9905
_cell_measurement_theta_min     3.03
_cell_measurement_theta_max     40.23
_cell_measurement_temperature     100(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.42
_exptl_crystal_size_mid     0.39
_exptl_crystal_size_min     0.24
_exptl_crystal_density_diffrn     1.398
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     664
_exptl_absorpt_coefficient_mu     0.347
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2004)
;
_exptl_absorpt_correction_T_min     0.8678
_exptl_absorpt_correction_T_max     0.9213
_exptl_special_details     ?
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
                      'Bruker Kappa goniometer with an APEXII CCD area detector'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     29484
_diffrn_reflns_av_R_equivalents     0.0217
_diffrn_reflns_av_sigmaI/netI     0.0106
_diffrn_reflns_theta_min     3.14
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -23
_diffrn_reflns_limit_k_max     23
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2673
_reflns_number_gt     2567
_reflns_threshold_expression     >2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0271
_refine_ls_R_factor_gt     0.0258
_refine_ls_wR_factor_gt     0.0659
_refine_ls_wR_factor_ref     0.0668
_refine_ls_goodness_of_fit_ref     1.081
_refine_ls_restrained_S_all     1.081
_refine_ls_number_reflns     2673
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0306P)²+0.8696P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.524
_refine_diff_density_min     -0.251
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     .
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'
    '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'
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_cell_refinement
;
SAINT-NT (Bruker, 2008)
;
_computing_data_reduction
;
SAINT-NT (Bruker, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.87719(10) 0.14944(5) 0.63203(12) 0.0192(2) Uani d . 1 1 . .
    H H1 0.9266 0.1503 0.5596 0.029 Uiso calc R 1 1 . .
    S S1 0.97650(3) 0.017169(17) 0.79264(4) 0.01571(12) Uani d P 0.9648(15) 1 A
                                                                               1
    S S1B 0.7585(15) -0.0370(8) 0.5105(18) 0.015(4) Uiso d P 0.0352(15) 1 A 2
    S S2 0.64591(4) 0.192805(18) 0.77639(4) 0.01717(13) Uani d P 0.9250(14) 1 A
                                                                               1
    S S2B 0.5665(6) 0.0391(3) 0.7355(7) 0.0115(16) Uiso d P 0.0750(14) 1 A 2
    C C1 0.83728(14) 0.02681(7) 0.62486(15) 0.0143(3) Uani d . 1 1 . .
    C C2 0.8000(2) -0.03234(10) 0.5456(2) 0.0196(4) Uani d . 1 1 A .
    H H2 0.7275 -0.0355 0.4499 0.023 Uiso calc R 1 1 . .
    C C3 0.88078(14) -0.09012(7) 0.62027(16) 0.0164(3) Uani d . 1 1 . .
    C C4 0.87069(15) -0.15970(7) 0.57672(17) 0.0211(3) Uani d . 1 1 A .
    H H4 0.8036 -0.1743 0.4833 0.025 Uiso calc R 1 1 . .
    C C5 0.95946(16) -0.20676(7) 0.67126(18) 0.0224(3) Uani d . 1 1 . .
    H H5 0.9526 -0.2539 0.6425 0.027 Uiso calc R 1 1 A .
    C C6 1.05924(15) -0.18589(7) 0.80878(17) 0.0212(3) Uani d . 1 1 A .
    H H6 1.1189 -0.2191 0.8723 0.025 Uiso calc R 1 1 . .
    C C7 1.07217(14) -0.11790(7) 0.85328(17) 0.0188(3) Uani d . 1 1 . .
    H H7 1.1404 -0.1037 0.9461 0.023 Uiso calc R 1 1 A .
    C C8 0.98227(14) -0.07031(7) 0.75833(16) 0.0155(3) Uani d . 1 1 A .
    C C9 0.66590(14) 0.10978(6) 0.70964(15) 0.0143(3) Uani d . 1 1 . .
    C C10 0.57303(17) 0.06420(12) 0.7569(2) 0.0207(4) Uani d . 1 1 A .
    H H10 0.5713 0.0167 0.7320 0.025 Uiso calc R 1 1 . .
    C C11 0.47804(14) 0.09599(7) 0.84862(16) 0.0167(3) Uani d . 1 1 . .
    C C12 0.36824(15) 0.06735(8) 0.91738(17) 0.0217(3) Uani d . 1 1 A .
    H H12 0.3466 0.0199 0.9052 0.026 Uiso calc R 1 1 . .
    C C13 0.29201(15) 0.10872(8) 1.00276(18) 0.0256(3) Uani d . 1 1 . .
    H H13 0.2181 0.0894 1.0503 0.031 Uiso calc R 1 1 A .
    C C14 0.32179(16) 0.17870(8) 1.02058(17) 0.0256(3) Uani d . 1 1 A .
    H H14 0.2682 0.2062 1.0806 0.031 Uiso calc R 1 1 . .
    C C15 0.42754(16) 0.20856(8) 0.95255(17) 0.0234(3) Uani d . 1 1 . .
    H H15 0.4465 0.2563 0.9634 0.028 Uiso calc R 1 1 A .
    C C16 0.50620(14) 0.16674(7) 0.86702(16) 0.0181(3) Uani d . 1 1 A .
    C C17 0.76939(14) 0.09720(7) 0.59569(16) 0.0151(3) Uani d . 1 1 A .
    C C18 0.68690(15) 0.10377(7) 0.42813(16) 0.0181(3) Uani d . 1 1 . .
    C C19 0.61967(16) 0.11146(8) 0.29504(18) 0.0250(3) Uani d . 1 1 A .
    H H19 0.5657 0.1176 0.1882 0.030 Uiso calc R 1 1 . .
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
    O1 C17 . 1.4301(16) ?
    O1 H1 . 0.8400 ?
    S1 C8 . 1.7346(13) ?
    S1 C1 . 1.7381(13) ?
    S1B C1 . 1.658(15) ?
    S1B C3 . 1.685(15) ?
    S2 C16 . 1.7282(14) ?
    S2 C9 . 1.7381(13) ?
    S2B C9 . 1.707(6) ?
    S2B C11 . 1.777(6) ?
    C1 C2 . 1.345(2) ?
    C1 C17 . 1.5152(18) ?
    C2 C3 . 1.435(2) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.4051(19) ?
    C3 C8 . 1.4060(19) ?
    C4 C5 . 1.384(2) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.401(2) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.378(2) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.3974(19) ?
    C7 H7 . 0.9500 ?
    C9 C10 . 1.364(2) ?
    C9 C17 . 1.5213(18) ?
    C10 C11 . 1.437(2) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.4016(19) ?
    C11 C16 . 1.409(2) ?
    C12 C13 . 1.377(2) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.397(2) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.377(2) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.397(2) ?
    C15 H15 . 0.9500 ?
    C17 C18 . 1.4762(18) ?
    C18 C19 . 1.183(2) ?
    C19 H19 . 0.9500 ?
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
    C17 O1 H1 . . 109.5 ?
    C8 S1 C1 . . 90.85(6) ?
    C1 S1B C3 . . 87.9(7) ?
    C16 S2 C9 . . 90.61(6) ?
    C9 S2B C11 . . 83.8(3) ?
    C2 C1 C17 . . 129.59(14) ?
    C17 C1 S1B . . 117.4(5) ?
    C2 C1 S1 . . 113.06(12) ?
    C17 C1 S1 . . 117.19(9) ?
    S1B C1 S1 . . 124.8(5) ?
    C1 C2 C3 . . 113.15(18) ?
    C1 C2 H2 . . 123.4 ?
    C3 C2 H2 . . 123.4 ?
    C4 C3 C8 . . 118.78(12) ?
    C4 C3 C2 . . 130.00(15) ?
    C8 C3 C2 . . 111.21(14) ?
    C4 C3 S1B . . 116.6(5) ?
    C8 C3 S1B . . 124.4(5) ?
    C5 C4 C3 . . 119.31(13) ?
    C5 C4 H4 . . 120.3 ?
    C3 C4 H4 . . 120.3 ?
    C4 C5 C6 . . 120.90(13) ?
    C4 C5 H5 . . 119.5 ?
    C6 C5 H5 . . 119.5 ?
    C7 C6 C5 . . 120.93(13) ?
    C7 C6 H6 . . 119.5 ?
    C5 C6 H6 . . 119.5 ?
    C6 C7 C8 . . 118.27(13) ?
    C6 C7 H7 . . 120.9 ?
    C8 C7 H7 . . 120.9 ?
    C7 C8 C3 . . 121.80(12) ?
    C7 C8 S1 . . 126.48(11) ?
    C3 C8 S1 . . 111.71(10) ?
    C10 C9 C17 . . 127.67(14) ?
    C17 C9 S2B . . 112.9(2) ?
    C10 C9 S2 . . 113.32(12) ?
    C17 C9 S2 . . 118.69(9) ?
    S2B C9 S2 . . 127.9(2) ?
    C9 C10 C11 . . 112.49(19) ?
    C9 C10 H10 . . 123.8 ?
    C11 C10 H10 . . 123.8 ?
    C12 C11 C16 . . 118.97(13) ?
    C12 C11 C10 . . 130.04(15) ?
    C16 C11 C10 . . 110.99(14) ?
    C12 C11 S2B . . 116.0(2) ?
    C16 C11 S2B . . 125.0(2) ?
    C13 C12 C11 . . 119.32(14) ?
    C13 C12 H12 . . 120.3 ?
    C11 C12 H12 . . 120.3 ?
    C12 C13 C14 . . 120.98(14) ?
    C12 C13 H13 . . 119.5 ?
    C14 C13 H13 . . 119.5 ?
    C15 C14 C13 . . 121.09(13) ?
    C15 C14 H14 . . 119.5 ?
    C13 C14 H14 . . 119.5 ?
    C14 C15 C16 . . 118.20(14) ?
    C14 C15 H15 . . 120.9 ?
    C16 C15 H15 . . 120.9 ?
    C15 C16 C11 . . 121.42(13) ?
    C15 C16 S2 . . 126.00(11) ?
    C11 C16 S2 . . 112.57(10) ?
    O1 C17 C18 . . 111.09(11) ?
    O1 C17 C1 . . 110.60(10) ?
    C18 C17 C1 . . 111.05(11) ?
    O1 C17 C9 . . 105.61(10) ?
    C18 C17 C9 . . 107.93(10) ?
    C1 C17 C9 . . 110.38(10) ?
    C19 C18 C17 . . 177.58(15) ?
    C18 C19 H19 . . 180.0 ?
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
    C3 S1B C1 C2 . . . . 16(2) ?
    C3 S1B C1 C17 . . . . -176.2(2) ?
    C3 S1B C1 S1 . . . . -5.3(8) ?
    C8 S1 C1 C2 . . . . -1.43(12) ?
    C8 S1 C1 C17 . . . . 174.39(10) ?
    C8 S1 C1 S1B . . . . 3.5(6) ?
    C17 C1 C2 C3 . . . . -173.51(12) ?
    S1B C1 C2 C3 . . . . -159(3) ?
    S1 C1 C2 C3 . . . . 1.67(18) ?
    C1 C2 C3 C4 . . . . 178.14(14) ?
    C1 C2 C3 C8 . . . . -1.03(19) ?
    C1 C2 C3 S1B . . . . 162(2) ?
    C1 S1B C3 C4 . . . . -179.5(3) ?
    C1 S1B C3 C8 . . . . 6.0(8) ?
    C1 S1B C3 C2 . . . . -13.5(18) ?
    C8 C3 C4 C5 . . . . 0.62(19) ?
    C2 C3 C4 C5 . . . . -178.49(15) ?
    S1B C3 C4 C5 . . . . -174.2(6) ?
    C3 C4 C5 C6 . . . . -0.3(2) ?
    C4 C5 C6 C7 . . . . -0.3(2) ?
    C5 C6 C7 C8 . . . . 0.5(2) ?
    C6 C7 C8 C3 . . . . -0.2(2) ?
    C6 C7 C8 S1 . . . . 178.61(10) ?
    C4 C3 C8 C7 . . . . -0.41(19) ?
    C2 C3 C8 C7 . . . . 178.87(13) ?
    S1B C3 C8 C7 . . . . 174.0(6) ?
    C4 C3 C8 S1 . . . . -179.34(10) ?
    C2 C3 C8 S1 . . . . -0.06(15) ?
    S1B C3 C8 S1 . . . . -5.0(6) ?
    C1 S1 C8 C7 . . . . -178.06(12) ?
    C1 S1 C8 C3 . . . . 0.81(10) ?
    C11 S2B C9 C10 . . . . 7.7(7) ?
    C11 S2B C9 C17 . . . . -174.53(13) ?
    C11 S2B C9 S2 . . . . -2.9(3) ?
    C16 S2 C9 C10 . . . . -1.27(11) ?
    C16 S2 C9 C17 . . . . 172.84(10) ?
    C16 S2 C9 S2B . . . . 1.6(3) ?
    C17 C9 C10 C11 . . . . -172.33(12) ?
    S2B C9 C10 C11 . . . . -169.8(10) ?
    S2 C9 C10 C11 . . . . 1.15(16) ?
    C9 C10 C11 C12 . . . . 179.65(14) ?
    C9 C10 C11 C16 . . . . -0.33(17) ?
    C9 C10 C11 S2B . . . . 169.8(10) ?
    C9 S2B C11 C12 . . . . -179.18(14) ?
    C9 S2B C11 C16 . . . . 3.7(3) ?
    C9 S2B C11 C10 . . . . -7.6(7) ?
    C16 C11 C12 C13 . . . . -0.8(2) ?
    C10 C11 C12 C13 . . . . 179.20(14) ?
    S2B C11 C12 C13 . . . . -178.1(2) ?
    C11 C12 C13 C14 . . . . 0.5(2) ?
    C12 C13 C14 C15 . . . . 0.4(2) ?
    C13 C14 C15 C16 . . . . -1.0(2) ?
    C14 C15 C16 C11 . . . . 0.7(2) ?
    C14 C15 C16 S2 . . . . -178.37(11) ?
    C12 C11 C16 C15 . . . . 0.25(19) ?
    C10 C11 C16 C15 . . . . -179.77(13) ?
    S2B C11 C16 C15 . . . . 177.3(2) ?
    C12 C11 C16 S2 . . . . 179.39(10) ?
    C10 C11 C16 S2 . . . . -0.63(15) ?
    S2B C11 C16 S2 . . . . -3.6(3) ?
    C9 S2 C16 C15 . . . . -179.84(12) ?
    C9 S2 C16 C11 . . . . 1.06(10) ?
    C2 C1 C17 O1 . . . . -146.09(15) ?
    S1B C1 C17 O1 . . . . -149.5(6) ?
    S1 C1 C17 O1 . . . . 38.90(13) ?
    C2 C1 C17 C18 . . . . -22.3(2) ?
    S1B C1 C17 C18 . . . . -25.7(6) ?
    S1 C1 C17 C18 . . . . 162.72(9) ?
    C2 C1 C17 C9 . . . . 97.40(17) ?
    S1B C1 C17 C9 . . . . 94.0(6) ?
    S1 C1 C17 C9 . . . . -77.61(12) ?
    C10 C9 C17 O1 . . . . -158.65(13) ?
    S2B C9 C17 O1 . . . . -159.4(2) ?
    S2 C9 C17 O1 . . . . 28.18(13) ?
    C10 C9 C17 C18 . . . . 82.46(17) ?
    S2B C9 C17 C18 . . . . 81.8(2) ?
    S2 C9 C17 C18 . . . . -90.71(12) ?
    C10 C9 C17 C1 . . . . -39.07(18) ?
    S2B C9 C17 C1 . . . . -39.8(2) ?
    S2 C9 C17 C1 . . . . 147.75(9) ?
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
    C6 H6 O1 2_746 0.95 2.57 3.2896(17) 133.0
    C2 H2 S2B 3_656 0.95 2.90 3.785(6) 155.3
    O1 H1 Cg1 3_756 0.84 2.69 3.5126(10) 166.3
    C13 H13 Cg5 3_657 0.95 2.82 3.7041(14) 154.6
    C19 H19 Cg2 1_554 0.95 2.42 3.3614(15) 171.6
