##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, 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           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2012-05-10
_journal_date_accepted     2012-06-05
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      7
_journal_page_first     o2028
_journal_page_last     o2028
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812025482
_journal_coeditor_code     YK2058
_publ_contact_author_name     'Prof. Uk Lee'
_publ_contact_author_address
;
 Department of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong
 Nam-gu, Busan 608-737, Republic of Korea
;
_publ_contact_author_email     'uklee@pknu.ac.kr'
_publ_contact_author_fax     '+82-51-629-5583'
_publ_contact_author_phone     '+82-51-629-5596'
_publ_section_title
;
5-Cyclopentyl-2-(3-fluorophenyl)-3-methylsulfinyl-1-benzofuran
;
loop_
    _publ_author_name
    _publ_author_address
    'Choi, Hong Dae'
;
 Department of Chemistry, Dongeui University, San 24 Kaya-dong
 Busanjin-gu, Busan 614-714, Republic of Korea
;
    'Seo, Pil Ja'
;
 Department of Chemistry, Dongeui University, San 24 Kaya-dong
 Busanjin-gu, Busan 614-714, Republic of Korea
;
    'Lee, Uk'
;
 Department of Chemistry, Pukyong National University,
 599-1 Daeyeon 3-dong
 Nam-gu, Busan 608-737, Republic of Korea
;
_publ_section_synopsis     .
data_I
_chemical_name_systematic
;
5-Cyclopentyl-2-(3-fluorophenyl)-3-methylsulfinyl-1-benzofuran
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H19 F O2 S'
_chemical_formula_sum     'C20 H19 F O2 S'
_chemical_formula_iupac     'C20 H19 F O2 S'
_chemical_formula_weight     342.41
_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     6.1024(3)
_cell_length_b     25.3030(11)
_cell_length_c     10.6840(5)
_cell_angle_alpha     90.00
_cell_angle_beta     90.2310(10)
_cell_angle_gamma     90.00
_cell_volume     1649.69(13)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5280
_cell_measurement_theta_min     2.50
_cell_measurement_theta_max     28.18
_cell_measurement_temperature     173(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.22
_exptl_crystal_density_diffrn     1.379
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     720
_exptl_absorpt_coefficient_mu     0.216
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.9188
_exptl_absorpt_correction_T_max     0.9536
_exptl_special_details     ?
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'rotating anode'
_diffrn_radiation_monochromator     'graphite multilayer'
_diffrn_measurement_device_type     'Bruker SMART APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     10.0
_diffrn_reflns_number     13224
_diffrn_reflns_av_R_equivalents     0.0272
_diffrn_reflns_av_sigmaI/netI     0.0204
_diffrn_reflns_theta_min     2.07
_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     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -30
_diffrn_reflns_limit_k_max     30
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     0
_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 > 2sigma(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     2905
_reflns_number_gt     2568
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0658
_refine_ls_R_factor_gt     0.0595
_refine_ls_wR_factor_gt     0.1578
_refine_ls_wR_factor_ref     0.1651
_refine_ls_goodness_of_fit_ref     1.021
_refine_ls_restrained_S_all     1.021
_refine_ls_number_reflns     2905
_refine_ls_number_parameters     228
_refine_ls_number_restraints     30
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0870P)²+2.8614P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.354
_refine_diff_density_min     -0.546
_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'
    'F' 'F' 0.0171 0.0103
                         '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, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
         'ORTEP3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998)'
_computing_publication_material     'SHELXL97 (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
    S S1 0.49517(11) 0.72428(3) 0.41704(6) 0.0274(2) Uani d . 1 2 . .
    O O1 0.5749(3) 0.56958(7) 0.45210(17) 0.0261(4) Uani d . 1 2 . .
    O O2 0.4494(4) 0.74049(8) 0.28532(19) 0.0403(6) Uani d . 1 2 . .
    F F1 1.2882(3) 0.56555(10) 0.6805(2) 0.0617(6) Uani d . 1 2 . .
    C C1 0.3984(4) 0.57030(11) 0.3714(2) 0.0245(6) Uani d . 1 2 . .
    C C2 0.6189(4) 0.62149(11) 0.4815(2) 0.0242(6) Uani d . 1 2 . .
    C C3 0.4786(4) 0.65466(11) 0.4202(2) 0.0234(6) Uani d . 1 2 . .
    C C4 0.1509(5) 0.63050(11) 0.2681(3) 0.0289(6) Uani d . 1 2 . .
    H H4 0.1049 0.6654 0.2488 0.035 Uiso calc R 1 2 . .
    C C5 0.0407(5) 0.58719(12) 0.2184(3) 0.0344(7) Uani d . 1 2 A .
    C C6 0.1179(5) 0.53590(12) 0.2453(3) 0.0356(7) Uani d . 1 2 . .
    H H6 0.0429 0.5066 0.2096 0.043 Uiso calc R 1 2 . .
    C C7 0.2976(5) 0.52630(11) 0.3211(3) 0.0306(6) Uani d . 1 2 . .
    H H7 0.3486 0.4915 0.3376 0.037 Uiso calc R 1 2 . .
    C C8 0.3310(4) 0.62182(10) 0.3474(2) 0.0233(6) Uani d . 1 2 . .
    C C9 -0.1701(6) 0.59386(12) 0.1427(3) 0.0448(8) Uani d DU 1 2 . .
    H H9A -0.2944 0.5837 0.1984 0.054 Uiso calc PR 0.803(16) 1 A 1
    H H9B -0.2753 0.5944 0.2142 0.054 Uiso d PR 0.197(16) 1 A 2
    C C10A -0.1826(10) 0.5586(2) 0.0271(5) 0.0527(19) Uani d PDU 0.803(16) 1 A 1
    H H10A -0.2053 0.5212 0.0505 0.063 Uiso calc PR 0.803(16) 1 A 1
    H H10B -0.0476 0.5615 -0.0236 0.063 Uiso calc PR 0.803(16) 1 A 1
    C C10B -0.283(3) 0.5505(2) 0.0671(11) 0.035(3) Uani d PDU 0.197(16) 1 A 2
    H H10C -0.3989 0.5330 0.1167 0.043 Uiso calc PR 0.197(16) 1 A 2
    H H10D -0.1763 0.5236 0.0390 0.043 Uiso calc PR 0.197(16) 1 A 2
    C C11 -0.3803(8) 0.58042(15) -0.0439(5) 0.0776(16) Uani d DU 1 1 . .
    H H11A -0.3541 0.5794 -0.1352 0.093 Uiso calc PR 0.803(16) 1 A 1
    H H11B -0.5127 0.5593 -0.0252 0.093 Uiso calc PR 0.803(16) 1 A 1
    H H11C -0.2866 0.5788 -0.1192 0.093 Uiso d PR 0.197(16) 1 A 2
    H H11D -0.5234 0.5637 -0.0628 0.093 Uiso d PR 0.197(16) 1 A 2
    C C12 -0.4100(5) 0.63712(13) 0.0002(3) 0.0377(7) Uani d . 1 2 A .
    H H12A -0.5526 0.6415 0.0428 0.045 Uiso calc R 1 2 . .
    H H12B -0.4034 0.6619 -0.0713 0.045 Uiso calc R 1 2 . .
    C C13 -0.2206(5) 0.64710(12) 0.0912(3) 0.0377(7) Uani d . 1 2 A .
    H H13A -0.0923 0.6620 0.0472 0.045 Uiso calc R 1 2 . .
    H H13B -0.2649 0.6717 0.1586 0.045 Uiso calc R 1 2 . .
    C C14 0.7931(4) 0.62945(11) 0.5734(2) 0.0258(6) Uani d . 1 2 . .
    C C15 0.9653(4) 0.59298(12) 0.5813(3) 0.0297(6) Uani d . 1 2 . .
    H H15 0.9718 0.5635 0.5263 0.036 Uiso calc R 1 2 . .
    C C16 1.1247(5) 0.60094(13) 0.6706(3) 0.0341(7) Uani d . 1 2 . .
    C C17 1.1235(5) 0.64302(14) 0.7524(3) 0.0390(8) Uani d . 1 2 . .
    H H17 1.2369 0.6474 0.8126 0.047 Uiso calc R 1 2 . .
    C C18 0.9526(5) 0.67855(13) 0.7442(3) 0.0380(7) Uani d . 1 2 . .
    H H18 0.9485 0.7079 0.7995 0.046 Uiso calc R 1 2 . .
    C C19 0.7870(5) 0.67197(12) 0.6566(3) 0.0304(6) Uani d . 1 2 . .
    H H19 0.6690 0.6964 0.6530 0.036 Uiso calc R 1 2 . .
    C C20 0.2521(5) 0.73842(12) 0.5038(3) 0.0339(7) Uani d . 1 2 . .
    H H20A 0.2213 0.7764 0.4998 0.051 Uiso calc R 1 2 . .
    H H20B 0.2733 0.7279 0.5913 0.051 Uiso calc R 1 2 . .
    H H20C 0.1286 0.7188 0.4679 0.051 Uiso calc R 1 2 . .
_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
    S1 O2 . 1.491(2) ?
    S1 C3 . 1.765(3) ?
    S1 C20 . 1.789(3) ?
    O1 C2 . 1.377(3) ?
    O1 C1 . 1.377(3) ?
    F1 C16 . 1.345(4) ?
    C1 C7 . 1.380(4) ?
    C1 C8 . 1.390(4) ?
    C2 C3 . 1.364(4) ?
    C2 C14 . 1.458(4) ?
    C3 C8 . 1.449(4) ?
    C4 C5 . 1.390(4) ?
    C4 C8 . 1.402(4) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.410(4) ?
    C5 C9 . 1.526(4) ?
    C6 C7 . 1.383(4) ?
    C6 H6 . 0.9500 ?
    C7 H7 . 0.9500 ?
    C9 C13 . 1.487(4) ?
    C9 C10A . 1.5249(16) ?
    C9 C10B . 1.5250(17) ?
    C9 H9A . 1.0000 ?
    C9 H9B . 1.0000 ?
    C10A C11 . 1.5254(17) ?
    C10A H10A . 0.9900 ?
    C10A H10B . 0.9900 ?
    C10B C11 . 1.5254(17) ?
    C10B H10C . 0.9900 ?
    C10B H10D . 0.9900 ?
    C11 C12 . 1.521(5) ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C11 H11C . 0.9900 ?
    C11 H11D . 0.9900 ?
    C12 C13 . 1.528(4) ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C14 C19 . 1.396(4) ?
    C14 C15 . 1.401(4) ?
    C15 C16 . 1.375(4) ?
    C15 H15 . 0.9500 ?
    C16 C17 . 1.377(5) ?
    C17 C18 . 1.379(5) ?
    C17 H17 . 0.9500 ?
    C18 C19 . 1.386(4) ?
    C18 H18 . 0.9500 ?
    C19 H19 . 0.9500 ?
    C20 H20A . 0.9800 ?
    C20 H20B . 0.9800 ?
    C20 H20C . 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
    O2 S1 C3 . . 106.38(12) ?
    O2 S1 C20 . . 106.37(14) ?
    C3 S1 C20 . . 98.18(13) ?
    C2 O1 C1 . . 106.34(19) ?
    O1 C1 C7 . . 125.4(2) ?
    O1 C1 C8 . . 111.0(2) ?
    C7 C1 C8 . . 123.6(2) ?
    C3 C2 O1 . . 110.9(2) ?
    C3 C2 C14 . . 133.8(3) ?
    O1 C2 C14 . . 115.2(2) ?
    C2 C3 C8 . . 107.0(2) ?
    C2 C3 S1 . . 126.0(2) ?
    C8 C3 S1 . . 126.7(2) ?
    C5 C4 C8 . . 119.0(3) ?
    C5 C4 H4 . . 120.5 ?
    C8 C4 H4 . . 120.5 ?
    C4 C5 C6 . . 119.2(3) ?
    C4 C5 C9 . . 121.4(3) ?
    C6 C5 C9 . . 119.3(3) ?
    C7 C6 C5 . . 123.0(3) ?
    C7 C6 H6 . . 118.5 ?
    C5 C6 H6 . . 118.5 ?
    C1 C7 C6 . . 116.0(3) ?
    C1 C7 H7 . . 122.0 ?
    C6 C7 H7 . . 122.0 ?
    C1 C8 C4 . . 119.3(2) ?
    C1 C8 C3 . . 104.8(2) ?
    C4 C8 C3 . . 135.9(2) ?
    C13 C9 C5 . . 118.0(3) ?
    C13 C9 C10A . . 102.7(3) ?
    C5 C9 C10A . . 113.8(3) ?
    C13 C9 C10B . . 111.3(3) ?
    C5 C9 C10B . . 125.4(5) ?
    C13 C9 H9A . . 107.2 ?
    C5 C9 H9A . . 107.2 ?
    C10A C9 H9A . . 107.2 ?
    C10B C9 H9A . . 77.8 ?
    C13 C9 H9B . . 97.9 ?
    C5 C9 H9B . . 98.0 ?
    C10A C9 H9B . . 126.7 ?
    C10B C9 H9B . . 97.2 ?
    C9 C10A C11 . . 103.2(3) ?
    C9 C10A H10A . . 111.1 ?
    C11 C10A H10A . . 111.1 ?
    C9 C10A H10B . . 111.1 ?
    C11 C10A H10B . . 111.1 ?
    H10A C10A H10B . . 109.1 ?
    C9 C10B C11 . . 103.2(3) ?
    C9 C10B H10C . . 111.1 ?
    C11 C10B H10C . . 111.1 ?
    C9 C10B H10D . . 111.1 ?
    C11 C10B H10D . . 111.1 ?
    H10C C10B H10D . . 109.1 ?
    C12 C11 C10B . . 105.9(5) ?
    C12 C11 C10A . . 106.4(3) ?
    C12 C11 H11A . . 110.5 ?
    C10B C11 H11A . . 133.6 ?
    C10A C11 H11A . . 110.5 ?
    C12 C11 H11B . . 110.5 ?
    C10B C11 H11B . . 83.8 ?
    C10A C11 H11B . . 110.5 ?
    H11A C11 H11B . . 108.6 ?
    C12 C11 H11C . . 111.1 ?
    C10B C11 H11C . . 112.7 ?
    C10A C11 H11C . . 86.0 ?
    H11B C11 H11C . . 128.0 ?
    C12 C11 H11D . . 111.1 ?
    C10B C11 H11D . . 106.7 ?
    C10A C11 H11D . . 130.0 ?
    H11A C11 H11D . . 86.2 ?
    H11C C11 H11D . . 109.2 ?
    C11 C12 C13 . . 105.2(2) ?
    C11 C12 H12A . . 110.7 ?
    C13 C12 H12A . . 110.7 ?
    C11 C12 H12B . . 110.7 ?
    C13 C12 H12B . . 110.7 ?
    H12A C12 H12B . . 108.8 ?
    C9 C13 C12 . . 103.9(2) ?
    C9 C13 H13A . . 111.0 ?
    C12 C13 H13A . . 111.0 ?
    C9 C13 H13B . . 111.0 ?
    C12 C13 H13B . . 111.0 ?
    H13A C13 H13B . . 109.0 ?
    C19 C14 C15 . . 119.4(3) ?
    C19 C14 C2 . . 120.9(2) ?
    C15 C14 C2 . . 119.6(3) ?
    C16 C15 C14 . . 118.3(3) ?
    C16 C15 H15 . . 120.9 ?
    C14 C15 H15 . . 120.9 ?
    F1 C16 C15 . . 118.7(3) ?
    F1 C16 C17 . . 118.1(3) ?
    C15 C16 C17 . . 123.2(3) ?
    C16 C17 C18 . . 118.1(3) ?
    C16 C17 H17 . . 121.0 ?
    C18 C17 H17 . . 121.0 ?
    C17 C18 C19 . . 120.9(3) ?
    C17 C18 H18 . . 119.5 ?
    C19 C18 H18 . . 119.5 ?
    C18 C19 C14 . . 120.1(3) ?
    C18 C19 H19 . . 119.9 ?
    C14 C19 H19 . . 119.9 ?
    S1 C20 H20A . . 109.5 ?
    S1 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    S1 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 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
    C2 O1 C1 C7 . . . . -178.4(3) ?
    C2 O1 C1 C8 . . . . 0.9(3) ?
    C1 O1 C2 C3 . . . . -1.1(3) ?
    C1 O1 C2 C14 . . . . 176.1(2) ?
    O1 C2 C3 C8 . . . . 0.9(3) ?
    C14 C2 C3 C8 . . . . -175.6(3) ?
    O1 C2 C3 S1 . . . . -172.60(18) ?
    C14 C2 C3 S1 . . . . 10.9(4) ?
    O2 S1 C3 C2 . . . . 137.4(2) ?
    C20 S1 C3 C2 . . . . -112.8(3) ?
    O2 S1 C3 C8 . . . . -34.9(3) ?
    C20 S1 C3 C8 . . . . 74.9(3) ?
    C8 C4 C5 C6 . . . . -2.3(4) ?
    C8 C4 C5 C9 . . . . 173.6(3) ?
    C4 C5 C6 C7 . . . . 1.1(5) ?
    C9 C5 C6 C7 . . . . -174.9(3) ?
    O1 C1 C7 C6 . . . . 177.9(3) ?
    C8 C1 C7 C6 . . . . -1.3(4) ?
    C5 C6 C7 C1 . . . . 0.7(5) ?
    O1 C1 C8 C4 . . . . -179.2(2) ?
    C7 C1 C8 C4 . . . . 0.1(4) ?
    O1 C1 C8 C3 . . . . -0.3(3) ?
    C7 C1 C8 C3 . . . . 179.0(3) ?
    C5 C4 C8 C1 . . . . 1.7(4) ?
    C5 C4 C8 C3 . . . . -176.7(3) ?
    C2 C3 C8 C1 . . . . -0.4(3) ?
    S1 C3 C8 C1 . . . . 173.1(2) ?
    C2 C3 C8 C4 . . . . 178.2(3) ?
    S1 C3 C8 C4 . . . . -8.3(5) ?
    C4 C5 C9 C13 . . . . 17.8(5) ?
    C6 C5 C9 C13 . . . . -166.4(3) ?
    C4 C5 C9 C10A . . . . 138.2(5) ?
    C6 C5 C9 C10A . . . . -45.9(5) ?
    C4 C5 C9 C10B . . . . 169.7(9) ?
    C6 C5 C9 C10B . . . . -14.5(10) ?
    C13 C9 C10A C11 . . . . -40.4(6) ?
    C5 C9 C10A C11 . . . . -169.1(4) ?
    C10B C9 C10A C11 . . . . 70.6(5) ?
    C13 C9 C10B C11 . . . . 7.3(14) ?
    C5 C9 C10B C11 . . . . -146.2(7) ?
    C10A C9 C10B C11 . . . . -70.6(5) ?
    C9 C10B C11 C12 . . . . -24.6(13) ?
    C9 C10B C11 C10A . . . . 70.6(5) ?
    C9 C10A C11 C12 . . . . 22.9(7) ?
    C9 C10A C11 C10B . . . . -70.6(5) ?
    C10B C11 C12 C13 . . . . 33.3(9) ?
    C10A C11 C12 C13 . . . . 2.6(6) ?
    C5 C9 C13 C12 . . . . 168.4(3) ?
    C10A C9 C13 C12 . . . . 42.3(4) ?
    C10B C9 C13 C12 . . . . 12.7(9) ?
    C11 C12 C13 C9 . . . . -27.9(4) ?
    C3 C2 C14 C19 . . . . 28.7(5) ?
    O1 C2 C14 C19 . . . . -147.7(3) ?
    C3 C2 C14 C15 . . . . -153.4(3) ?
    O1 C2 C14 C15 . . . . 30.2(3) ?
    C19 C14 C15 C16 . . . . -0.7(4) ?
    C2 C14 C15 C16 . . . . -178.7(3) ?
    C14 C15 C16 F1 . . . . 178.7(3) ?
    C14 C15 C16 C17 . . . . -0.2(4) ?
    F1 C16 C17 C18 . . . . -178.4(3) ?
    C15 C16 C17 C18 . . . . 0.5(5) ?
    C16 C17 C18 C19 . . . . 0.2(5) ?
    C17 C18 C19 C14 . . . . -1.1(5) ?
    C15 C14 C19 C18 . . . . 1.4(4) ?
    C2 C14 C19 C18 . . . . 179.2(3) ?
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
    C19 H19 O2 4_576 0.95 2.52 3.326(4) 142.6
    C20 H20B O2 4_576 0.98 2.47 3.279(4) 140.2
    C9 H9A Cg1 1_455 1.00 2.76 3.626(4) 145.4
    C15 H15 Cg2 1_655 0.95 2.94 3.461(4) 116.1
