#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/06/2230653.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_2230653
loop_
_publ_author_name
'Seo, Pil Ja'
'Choi, Hong Dae'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 3-Cyclopentylsulfonyl-5-fluoro-2-methyl-1-benzofuran
;
_journal_coeditor_code           GO2016
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1689
_journal_paper_doi               10.1107/S1600536811021222
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H15 F O3 S'
_chemical_formula_moiety         'C14 H15 F O3 S'
_chemical_formula_sum            'C14 H15 F O3 S'
_chemical_formula_weight         282.32
_chemical_melting_point_gt       394
_chemical_melting_point_lt       395
_chemical_name_systematic
;
3-Cyclopentylsulfonyl-5-fluoro-2-methyl-1-benzofuran
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                95.033(4)
_cell_angle_beta                 109.140(4)
_cell_angle_gamma                91.229(4)
_cell_formula_units_Z            4
_cell_length_a                   10.0568(8)
_cell_length_b                   10.2697(8)
_cell_length_c                   13.2894(10)
_cell_measurement_reflns_used    6383
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.06
_cell_measurement_theta_min      2.22
_cell_volume                     1289.82(18)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  'graphite multilayer'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21777
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.63
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.9481
_exptl_absorpt_correction_T_min  0.9355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.306
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5565
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0452
_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)+(0.0514P)²+0.6137P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1189
_reflns_number_gt                4022
_reflns_number_total             5565
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            go2016.cif
_cod_data_source_block           I
_cod_original_cell_volume        1289.82(17)
_cod_database_code               2230653
_cod_database_fobs_code          2230653
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.23453(6) 0.33785(5) 0.23641(4) 0.03150(15) Uani d . 1 2 . .
F F1 0.81952(14) 0.46170(14) 0.28853(11) 0.0484(4) Uani d . 1 2 . .
O O1 0.40319(15) 0.10269(14) 0.07061(11) 0.0326(4) Uani d . 1 2 . .
O O2 0.09116(17) 0.32983(18) 0.16639(13) 0.0460(4) Uani d . 1 2 . .
C C1 0.3369(2) 0.2567(2) 0.17088(16) 0.0269(4) Uani d . 1 2 . .
C C2 0.4835(2) 0.28575(19) 0.18530(15) 0.0252(4) Uani d . 1 2 . .
O O3 0.30185(18) 0.46418(15) 0.27859(14) 0.0438(4) Uani d . 1 2 . .
C C3 0.5859(2) 0.3822(2) 0.24350(16) 0.0296(5) Uani d . 1 2 . .
H H3 0.5664 0.4524 0.2872 0.036 Uiso calc R 1 2 . .
C C4 0.7165(2) 0.3693(2) 0.23369(17) 0.0311(5) Uani d . 1 2 . .
C C5 0.7522(2) 0.2698(2) 0.17204(18) 0.0344(5) Uani d . 1 2 . .
H H5 0.8456 0.2666 0.1699 0.041 Uiso calc R 1 2 . .
C C6 0.6504(2) 0.1750(2) 0.11357(17) 0.0333(5) Uani d . 1 2 . .
H H6 0.6704 0.1051 0.0699 0.040 Uiso calc R 1 2 . .
C C7 0.5185(2) 0.1872(2) 0.12172(16) 0.0280(5) Uani d . 1 2 . .
C C8 0.2955(2) 0.1465(2) 0.10210(16) 0.0305(5) Uani d . 1 2 . .
C C9 0.1621(2) 0.0657(2) 0.05858(19) 0.0411(6) Uani d . 1 2 . .
H H9A 0.1435 0.0392 -0.0177 0.062 Uiso calc R 1 2 . .
H H9B 0.0847 0.1166 0.0675 0.062 Uiso calc R 1 2 . .
H H9C 0.1697 -0.0125 0.0971 0.062 Uiso calc R 1 2 . .
C C10 0.2422(2) 0.2431(2) 0.34337(17) 0.0310(5) Uani d . 1 2 . .
H H10 0.2079 0.1510 0.3140 0.037 Uiso calc R 1 2 . .
C C11 0.3910(3) 0.2436(2) 0.42411(18) 0.0396(6) Uani d . 1 2 . .
H H11A 0.4133 0.1548 0.4460 0.048 Uiso calc R 1 2 . .
H H11B 0.4617 0.2748 0.3933 0.048 Uiso calc R 1 2 . .
C C12 0.3888(3) 0.3373(3) 0.5190(2) 0.0514(7) Uani d . 1 2 . .
H H12A 0.4612 0.3171 0.5860 0.062 Uiso calc R 1 2 . .
H H12B 0.4047 0.4293 0.5070 0.062 Uiso calc R 1 2 . .
C C13 0.2438(3) 0.3130(3) 0.5228(2) 0.0510(7) Uani d . 1 2 . .
H H13A 0.2174 0.3868 0.5643 0.061 Uiso calc R 1 2 . .
H H13B 0.2374 0.2315 0.5560 0.061 Uiso calc R 1 2 . .
C C14 0.1491(3) 0.3006(2) 0.40645(19) 0.0405(6) Uani d . 1 2 . .
H H14A 0.1171 0.3872 0.3839 0.049 Uiso calc R 1 2 . .
H H14B 0.0654 0.2414 0.3954 0.049 Uiso calc R 1 2 . .
S S2 0.97507(6) 0.86902(6) 0.24244(5) 0.03691(16) Uani d . 1 2 . .
F F2 0.43771(16) 0.96231(15) 0.28861(13) 0.0589(4) Uani d . 1 2 . .
O O4 0.67248(16) 0.60770(14) 0.08407(12) 0.0359(4) Uani d . 1 2 . .
O O5 0.93729(18) 1.00229(16) 0.24654(16) 0.0536(5) Uani d . 1 2 . .
O O6 1.07814(18) 0.83460(19) 0.19339(15) 0.0534(5) Uani d . 1 2 . .
C C15 0.8217(2) 0.7728(2) 0.17896(17) 0.0308(5) Uani d . 1 2 . .
C C16 0.6865(2) 0.7948(2) 0.19121(16) 0.0290(5) Uani d . 1 2 . .
C C17 0.6327(2) 0.8908(2) 0.24526(17) 0.0332(5) Uani d . 1 2 . .
H H17 0.6884 0.9657 0.2853 0.040 Uiso calc R 1 2 . .
C C18 0.4942(3) 0.8703(2) 0.23702(19) 0.0399(6) Uani d . 1 2 . .
C C19 0.4080(3) 0.7648(2) 0.1794(2) 0.0424(6) Uani d . 1 2 . .
H H19 0.3129 0.7566 0.1776 0.051 Uiso calc R 1 2 . .
C C20 0.4606(2) 0.6713(2) 0.12428(19) 0.0387(5) Uani d . 1 2 . .
H H20 0.4039 0.5976 0.0830 0.046 Uiso calc R 1 2 . .
C C21 0.5994(2) 0.6900(2) 0.13206(17) 0.0312(5) Uani d . 1 2 . .
C C22 0.8073(2) 0.6592(2) 0.11486(17) 0.0334(5) Uani d . 1 2 . .
C C23 0.9032(3) 0.5815(3) 0.0738(2) 0.0456(6) Uani d . 1 2 . .
H H23A 0.9124 0.4962 0.1026 0.068 Uiso calc R 1 2 . .
H H23B 0.9960 0.6279 0.0961 0.068 Uiso calc R 1 2 . .
H H23C 0.8650 0.5686 -0.0045 0.068 Uiso calc R 1 2 . .
C C24 1.0323(2) 0.8246(2) 0.37518(18) 0.0367(5) Uani d . 1 2 A .
H H24 0.9527 0.8329 0.4044 0.044 Uiso calc R 1 2 . .
C C25 1.1571(3) 0.9139(3) 0.4469(2) 0.0526(7) Uani d . 1 2 A .
H H25A 1.2183 0.9408 0.4064 0.063 Uiso calc R 1 2 . .
H H25B 1.1246 0.9932 0.4779 0.063 Uiso calc R 1 2 . .
C C26 1.2325(3) 0.8310(2) 0.5315(2) 0.0665(9) Uani d D 1 2 . .
H H26A 1.1804 0.8185 0.5819 0.080 Uiso calc PR 0.60(2) 1 A 1
H H26B 1.3293 0.8672 0.5719 0.080 Uiso calc PR 0.60(2) 1 A 1
H H26C 1.1987 0.8460 0.5934 0.080 Uiso d PR 0.40(2) 1 A 2
H H26D 1.3349 0.8542 0.5562 0.080 Uiso d PR 0.40(2) 1 A 2
C C27A 1.2327(6) 0.7051(8) 0.4620(8) 0.060(3) Uani d PDU 0.60(2) 1 A 1
H H27A 1.3006 0.7139 0.4230 0.072 Uiso calc PR 0.60(2) 1 A 1
H H27B 1.2574 0.6306 0.5058 0.072 Uiso calc PR 0.60(2) 1 A 1
C C27B 1.1998(14) 0.6866(3) 0.4914(7) 0.050(3) Uani d PDU 0.40(2) 1 A 2
H H27C 1.2837 0.6453 0.4824 0.060 Uiso calc PR 0.40(2) 1 A 2
H H27D 1.1679 0.6392 0.5419 0.060 Uiso calc PR 0.40(2) 1 A 2
C C28 1.0829(3) 0.6861(2) 0.3846(2) 0.0429(6) Uani d D 1 2 . .
H H28A 1.0237 0.6318 0.4132 0.051 Uiso calc PR 0.60(2) 1 A 1
H H28B 1.0810 0.6439 0.3142 0.051 Uiso calc PR 0.60(2) 1 A 1
H H28C 1.012(7) 0.612(7) 0.354(5) 0.051 Uiso d P 0.40(2) 1 A 2
H H28D 1.134(8) 0.675(7) 0.343(5) 0.051 Uiso d P 0.40(2) 1 A 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'
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'
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
O3 S1 O2 . . 118.65(11) ?
O3 S1 C1 . . 107.46(10) ?
O2 S1 C1 . . 108.81(10) ?
O3 S1 C10 . . 109.46(10) ?
O2 S1 C10 . . 107.34(10) ?
C1 S1 C10 . . 104.18(10) ?
C8 O1 C7 . . 107.10(15) ?
C8 C1 C2 . . 107.13(19) ?
C8 C1 S1 . . 125.44(16) ?
C2 C1 S1 . . 127.23(16) ?
C7 C2 C3 . . 119.14(19) ?
C7 C2 C1 . . 104.77(17) ?
C3 C2 C1 . . 136.1(2) ?
C4 C3 C2 . . 115.69(19) ?
C4 C3 H3 . . 122.2 ?
C2 C3 H3 . . 122.2 ?
F1 C4 C3 . . 117.72(19) ?
F1 C4 C5 . . 117.06(19) ?
C3 C4 C5 . . 125.22(19) ?
C6 C5 C4 . . 119.1(2) ?
C6 C5 H5 . . 120.5 ?
C4 C5 H5 . . 120.5 ?
C7 C6 C5 . . 116.5(2) ?
C7 C6 H6 . . 121.8 ?
C5 C6 H6 . . 121.8 ?
C6 C7 O1 . . 125.45(19) ?
C6 C7 C2 . . 124.39(19) ?
O1 C7 C2 . . 110.14(18) ?
O1 C8 C1 . . 110.84(17) ?
O1 C8 C9 . . 115.52(19) ?
C1 C8 C9 . . 133.6(2) ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C11 C10 C14 . . 106.14(18) ?
C11 C10 S1 . . 112.41(15) ?
C14 C10 S1 . . 110.05(16) ?
C11 C10 H10 . . 109.4 ?
C14 C10 H10 . . 109.4 ?
S1 C10 H10 . . 109.4 ?
C12 C11 C10 . . 104.7(2) ?
C12 C11 H11A . . 110.8 ?
C10 C11 H11A . . 110.8 ?
C12 C11 H11B . . 110.8 ?
C10 C11 H11B . . 110.8 ?
H11A C11 H11B . . 108.9 ?
C13 C12 C11 . . 103.0(2) ?
C13 C12 H12A . . 111.2 ?
C11 C12 H12A . . 111.2 ?
C13 C12 H12B . . 111.2 ?
C11 C12 H12B . . 111.2 ?
H12A C12 H12B . . 109.1 ?
C12 C13 C14 . . 104.7(2) ?
C12 C13 H13A . . 110.8 ?
C14 C13 H13A . . 110.8 ?
C12 C13 H13B . . 110.8 ?
C14 C13 H13B . . 110.8 ?
H13A C13 H13B . . 108.9 ?
C13 C14 C10 . . 104.66(19) ?
C13 C14 H14A . . 110.8 ?
C10 C14 H14A . . 110.8 ?
C13 C14 H14B . . 110.8 ?
C10 C14 H14B . . 110.8 ?
H14A C14 H14B . . 108.9 ?
O6 S2 O5 . . 118.23(11) ?
O6 S2 C15 . . 109.20(11) ?
O5 S2 C15 . . 107.56(10) ?
O6 S2 C24 . . 109.04(11) ?
O5 S2 C24 . . 107.64(11) ?
C15 S2 C24 . . 104.28(10) ?
C22 O4 C21 . . 107.03(16) ?
C22 C15 C16 . . 107.17(19) ?
C22 C15 S2 . . 127.18(18) ?
C16 C15 S2 . . 125.52(17) ?
C21 C16 C17 . . 119.4(2) ?
C21 C16 C15 . . 105.14(19) ?
C17 C16 C15 . . 135.4(2) ?
C18 C17 C16 . . 115.7(2) ?
C18 C17 H17 . . 122.2 ?
C16 C17 H17 . . 122.2 ?
F2 C18 C17 . . 117.4(2) ?
F2 C18 C19 . . 117.8(2) ?
C17 C18 C19 . . 124.8(2) ?
C20 C19 C18 . . 119.4(2) ?
C20 C19 H19 . . 120.3 ?
C18 C19 H19 . . 120.3 ?
C21 C20 C19 . . 116.5(2) ?
C21 C20 H20 . . 121.7 ?
C19 C20 H20 . . 121.7 ?
C20 C21 O4 . . 125.7(2) ?
C20 C21 C16 . . 124.1(2) ?
O4 C21 C16 . . 110.18(19) ?
C15 C22 O4 . . 110.5(2) ?
C15 C22 C23 . . 134.7(2) ?
O4 C22 C23 . . 114.8(2) ?
C22 C23 H23A . . 109.5 ?
C22 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C22 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
C28 C24 C25 . . 105.42(19) ?
C28 C24 S2 . . 113.88(17) ?
C25 C24 S2 . . 111.11(17) ?
C28 C24 H24 . . 108.8 ?
C25 C24 H24 . . 108.8 ?
S2 C24 H24 . . 108.8 ?
C26 C25 C24 . . 103.5(2) ?
C26 C25 H25A . . 111.1 ?
C24 C25 H25A . . 111.1 ?
C26 C25 H25B . . 111.1 ?
C24 C25 H25B . . 111.1 ?
H25A C25 H25B . . 109.0 ?
C25 C26 C27B . . 110.6(2) ?
C25 C26 C27A . . 99.5(5) ?
C25 C26 H26A . . 111.9 ?
C27B C26 H26A . . 88.1 ?
C27A C26 H26A . . 111.9 ?
C25 C26 H26B . . 111.9 ?
C27B C26 H26B . . 122.4 ?
C27A C26 H26B . . 111.9 ?
H26A C26 H26B . . 109.6 ?
C25 C26 H26C . . 109.7 ?
C27B C26 H26C . . 106.2 ?
C27A C26 H26C . . 129.9 ?
H26B C26 H26C . . 94.1 ?
C25 C26 H26D . . 110.0 ?
C27B C26 H26D . . 111.9 ?
C27A C26 H26D . . 98.1 ?
H26A C26 H26D . . 122.4 ?
H26C C26 H26D . . 108.3 ?
C28 C27A C26 . . 104.3(2) ?
C28 C27A H27A . . 110.9 ?
C26 C27A H27A . . 110.9 ?
C28 C27A H27B . . 110.9 ?
C26 C27A H27B . . 110.9 ?
H27A C27A H27B . . 108.9 ?
C26 C27A H28D . . 124(3) ?
H27A C27A H28D . . 78.9 ?
H27B C27A H28D . . 117.5 ?
C28 C27B C26 . . 104.3(2) ?
C28 C27B H27C . . 110.9 ?
C26 C27B H27C . . 110.9 ?
C28 C27B H27D . . 110.9 ?
C26 C27B H27D . . 110.9 ?
H27C C27B H27D . . 108.9 ?
C27A C28 C24 . . 103.9(3) ?
C27B C28 C24 . . 107.6(3) ?
C27A C28 H28A . . 111.0 ?
C27B C28 H28A . . 88.1 ?
C24 C28 H28A . . 111.0 ?
C27A C28 H28B . . 111.0 ?
C27B C28 H28B . . 127.7 ?
C24 C28 H28B . . 111.0 ?
H28A C28 H28B . . 109.0 ?
C27A C28 H28C . . 137(4) ?
C27B C28 H28C . . 123(4) ?
C24 C28 H28C . . 118(4) ?
H28A C28 H28C . . 45.4 ?
H28B C28 H28C . . 64.8 ?
C27A C28 H28D . . 76(4) ?
C27B C28 H28D . . 98(5) ?
C24 C28 H28D . . 107(5) ?
H28A C28 H28D . . 137.9 ?
H28C C28 H28D . . 100(6) ?
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 O3 . 1.4289(17) ?
S1 O2 . 1.4329(17) ?
S1 C1 . 1.735(2) ?
S1 C10 . 1.774(2) ?
F1 C4 . 1.359(2) ?
O1 C8 . 1.355(3) ?
O1 C7 . 1.377(2) ?
C1 C8 . 1.356(3) ?
C1 C2 . 1.444(3) ?
C2 C7 . 1.387(3) ?
C2 C3 . 1.392(3) ?
C3 C4 . 1.370(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.381(3) ?
C5 C6 . 1.379(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.373(3) ?
C6 H6 . 0.9500 ?
C8 C9 . 1.478(3) ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 C11 . 1.528(3) ?
C10 C14 . 1.543(3) ?
C10 H10 . 1.0000 ?
C11 C12 . 1.524(3) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.492(4) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C14 . 1.520(3) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
S2 O6 . 1.4292(19) ?
S2 O5 . 1.4294(18) ?
S2 C15 . 1.733(2) ?
S2 C24 . 1.771(2) ?
F2 C18 . 1.360(3) ?
O4 C22 . 1.362(3) ?
O4 C21 . 1.379(3) ?
C15 C22 . 1.358(3) ?
C15 C16 . 1.442(3) ?
C16 C21 . 1.380(3) ?
C16 C17 . 1.390(3) ?
C17 C18 . 1.372(3) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.375(3) ?
C19 C20 . 1.375(3) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.374(3) ?
C20 H20 . 0.9500 ?
C22 C23 . 1.471(3) ?
C23 H23A . 0.9800 ?
C23 H23B . 0.9800 ?
C23 H23C . 0.9800 ?
C24 C28 . 1.523(3) ?
C24 C25 . 1.529(3) ?
C24 H24 . 1.0000 ?
C25 C26 . 1.484(4) ?
C25 H25A . 0.9900 ?
C25 H25B . 0.9900 ?
C26 C27B . 1.522(2) ?
C26 C27A . 1.522(2) ?
C26 H26A . 0.9900 ?
C26 H26B . 0.9900 ?
C26 H26C . 0.9900 ?
C26 H26D . 0.9900 ?
C27A C28 . 1.5166(18) ?
C27A H27A . 0.9900 ?
C27A H27B . 0.9900 ?
C27B C28 . 1.5171(18) ?
C27B H27C . 0.9900 ?
C27B H27D . 0.9900 ?
C28 H28A . 0.9900 ?
C28 H28B . 0.9900 ?
C28 H28C . 0.99(7) ?
C28 H28D . 0.87(7) ?
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
C9 H9C O6 1_445 0.98 2.45 3.348(3) 152
C19 H19 O6 1_455 0.95 2.58 3.469(3) 157
C23 H23A O2 1_655 0.98 2.50 3.318(3) 141
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
O3 S1 C1 C8 . . . . -165.58(19) ?
O2 S1 C1 C8 . . . . -35.9(2) ?
C10 S1 C1 C8 . . . . 78.3(2) ?
O3 S1 C1 C2 . . . . 20.1(2) ?
O2 S1 C1 C2 . . . . 149.75(18) ?
C10 S1 C1 C2 . . . . -96.00(19) ?
C8 C1 C2 C7 . . . . 0.0(2) ?
S1 C1 C2 C7 . . . . 175.20(16) ?
C8 C1 C2 C3 . . . . 179.9(2) ?
S1 C1 C2 C3 . . . . -4.9(4) ?
C7 C2 C3 C4 . . . . -1.0(3) ?
C1 C2 C3 C4 . . . . 179.1(2) ?
C2 C3 C4 F1 . . . . 179.56(18) ?
C2 C3 C4 C5 . . . . -0.2(3) ?
F1 C4 C5 C6 . . . . -178.90(19) ?
C3 C4 C5 C6 . . . . 0.9(4) ?
C4 C5 C6 C7 . . . . -0.2(3) ?
C5 C6 C7 O1 . . . . -179.5(2) ?
C5 C6 C7 C2 . . . . -1.1(3) ?
C8 O1 C7 C6 . . . . 178.1(2) ?
C8 O1 C7 C2 . . . . -0.5(2) ?
C3 C2 C7 C6 . . . . 1.8(3) ?
C1 C2 C7 C6 . . . . -178.4(2) ?
C3 C2 C7 O1 . . . . -179.60(17) ?
C1 C2 C7 O1 . . . . 0.3(2) ?
C7 O1 C8 C1 . . . . 0.5(2) ?
C7 O1 C8 C9 . . . . -177.92(18) ?
C2 C1 C8 O1 . . . . -0.3(2) ?
S1 C1 C8 O1 . . . . -175.62(14) ?
C2 C1 C8 C9 . . . . 177.7(2) ?
S1 C1 C8 C9 . . . . 2.4(4) ?
O3 S1 C10 C11 . . . . -50.09(18) ?
O2 S1 C10 C11 . . . . 179.88(16) ?
C1 S1 C10 C11 . . . . 64.59(18) ?
O3 S1 C10 C14 . . . . 67.98(17) ?
O2 S1 C10 C14 . . . . -62.05(17) ?
C1 S1 C10 C14 . . . . -177.34(15) ?
C14 C10 C11 C12 . . . . -17.1(2) ?
S1 C10 C11 C12 . . . . 103.3(2) ?
C10 C11 C12 C13 . . . . 36.0(3) ?
C11 C12 C13 C14 . . . . -41.4(3) ?
C12 C13 C14 C10 . . . . 30.6(3) ?
C11 C10 C14 C13 . . . . -7.9(2) ?
S1 C10 C14 C13 . . . . -129.75(18) ?
O6 S2 C15 C22 . . . . 17.4(2) ?
O5 S2 C15 C22 . . . . 146.8(2) ?
C24 S2 C15 C22 . . . . -99.1(2) ?
O6 S2 C15 C16 . . . . -167.32(18) ?
O5 S2 C15 C16 . . . . -37.9(2) ?
C24 S2 C15 C16 . . . . 76.3(2) ?
C22 C15 C16 C21 . . . . 0.1(2) ?
S2 C15 C16 C21 . . . . -176.02(16) ?
C22 C15 C16 C17 . . . . -180.0(2) ?
S2 C15 C16 C17 . . . . 3.9(4) ?
C21 C16 C17 C18 . . . . 1.7(3) ?
C15 C16 C17 C18 . . . . -178.2(2) ?
C16 C17 C18 F2 . . . . -179.82(19) ?
C16 C17 C18 C19 . . . . -0.8(4) ?
F2 C18 C19 C20 . . . . 178.6(2) ?
C17 C18 C19 C20 . . . . -0.5(4) ?
C18 C19 C20 C21 . . . . 0.7(3) ?
C19 C20 C21 O4 . . . . 179.4(2) ?
C19 C20 C21 C16 . . . . 0.3(3) ?
C22 O4 C21 C20 . . . . -177.9(2) ?
C22 O4 C21 C16 . . . . 1.3(2) ?
C17 C16 C21 C20 . . . . -1.6(3) ?
C15 C16 C21 C20 . . . . 178.4(2) ?
C17 C16 C21 O4 . . . . 179.21(18) ?
C15 C16 C21 O4 . . . . -0.8(2) ?
C16 C15 C22 O4 . . . . 0.7(2) ?
S2 C15 C22 O4 . . . . 176.73(15) ?
C16 C15 C22 C23 . . . . -178.4(2) ?
S2 C15 C22 C23 . . . . -2.4(4) ?
C21 O4 C22 C15 . . . . -1.2(2) ?
C21 O4 C22 C23 . . . . 178.08(18) ?
O6 S2 C24 C28 . . . . -47.9(2) ?
O5 S2 C24 C28 . . . . -177.32(17) ?
C15 S2 C24 C28 . . . . 68.63(19) ?
O6 S2 C24 C25 . . . . 70.9(2) ?
O5 S2 C24 C25 . . . . -58.5(2) ?
C15 S2 C24 C25 . . . . -172.52(18) ?
C28 C24 C25 C26 . . . . -29.6(3) ?
S2 C24 C25 C26 . . . . -153.4(2) ?
C24 C25 C26 C27B . . . . 23.9(8) ?
C24 C25 C26 C27A . . . . 45.8(5) ?
C25 C26 C27A C28 . . . . -46.0(9) ?
C27B C26 C27A C28 . . . . 74.3(4) ?
C25 C26 C27B C28 . . . . -8.7(12) ?
C27A C26 C27B C28 . . . . -74.2(4) ?
C26 C27A C28 C27B . . . . -74.3(4) ?
C26 C27A C28 C24 . . . . 27.8(10) ?
C26 C27B C28 C27A . . . . 74.2(4) ?
C26 C27B C28 C24 . . . . -10.5(12) ?
C25 C24 C28 C27A . . . . 0.6(7) ?
S2 C24 C28 C27A . . . . 122.7(6) ?
C25 C24 C28 C27B . . . . 25.2(8) ?
S2 C24 C28 C27B . . . . 147.2(8) ?
