# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ch14573

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H14 S6'
_chemical_formula_sum            'C28 H14 S6'
_chemical_formula_weight         542.75

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.9639(18)
_cell_length_b                   7.509(2)
_cell_length_c                   50.362(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.826(7)
_cell_angle_gamma                90.00
_cell_volume                     2252.5(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8443
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12233
_diffrn_reflns_av_R_equivalents  0.1507
_diffrn_reflns_av_sigmaI/netI    0.1898
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -59
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_theta_min         0.81
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3952
_reflns_number_gt                1562
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1074P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3952
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2014
_refine_ls_R_factor_gt           0.0698
_refine_ls_wR_factor_ref         0.2479
_refine_ls_wR_factor_gt          0.1613
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_restrained_S_all      0.957
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0285(15) 0.5650(14) 0.39158(17) 0.025(3) Uani 1 1 d . . .
C2 C 0.1091(15) 0.5583(15) 0.41975(18) 0.028(3) Uani 1 1 d . . .
C3 C -0.0193(16) 0.6377(15) 0.43889(19) 0.034(3) Uani 1 1 d . . .
H3 H -0.1529 0.6950 0.4338 0.041 Uiso 1 1 calc R . .
C4 C 0.0526(18) 0.6311(16) 0.4656(2) 0.044(3) Uani 1 1 d . . .
H4 H -0.0369 0.6792 0.4784 0.053 Uiso 1 1 calc R . .
C5 C 0.2579(18) 0.5528(16) 0.4733(2) 0.044(3) Uani 1 1 d . . .
H5 H 0.3088 0.5537 0.4911 0.052 Uiso 1 1 calc R . .
C6 C 0.384(2) 0.4744(16) 0.4544(2) 0.051(4) Uani 1 1 d . . .
H6 H 0.5190 0.4180 0.4593 0.061 Uiso 1 1 calc R . .
C7 C 0.3090(15) 0.4803(14) 0.42782(19) 0.033(3) Uani 1 1 d . . .
H7 H 0.3971 0.4296 0.4151 0.040 Uiso 1 1 calc R . .
C8 C -0.1763(16) 0.6211(14) 0.38097(16) 0.025(2) Uani 1 1 d . . .
H8 H -0.2925 0.6620 0.3910 0.030 Uiso 1 1 calc R . .
C9 C -0.1890(14) 0.6091(14) 0.35281(17) 0.023(2) Uani 1 1 d . . .
C10 C 0.0058(15) 0.5383(14) 0.34215(17) 0.023(2) Uani 1 1 d . . .
C11 C -0.0083(14) 0.5379(13) 0.31382(17) 0.021(2) Uani 1 1 d . . .
C12 C -0.2083(13) 0.6071(14) 0.30332(17) 0.023(2) Uani 1 1 d . . .
C13 C -0.2193(15) 0.6273(14) 0.27543(17) 0.028(3) Uani 1 1 d . . .
H13 H -0.3418 0.6742 0.2656 0.033 Uiso 1 1 calc R . .
C14 C -0.0276(15) 0.5690(13) 0.26472(18) 0.022(2) Uani 1 1 d . . .
C15 C 0.0291(14) 0.5696(14) 0.23719(17) 0.025(3) Uani 1 1 d . . .
C16 C 0.2215(16) 0.5129(13) 0.22648(18) 0.026(3) Uani 1 1 d . . .
H16 H 0.3458 0.4688 0.2362 0.031 Uiso 1 1 calc R . .
C17 C 0.2065(14) 0.5303(14) 0.19822(18) 0.027(3) Uani 1 1 d . . .
C18 C 0.0076(14) 0.6017(15) 0.18820(17) 0.025(2) Uani 1 1 d . . .
C19 C -0.0028(15) 0.5996(14) 0.15926(17) 0.026(2) Uani 1 1 d . . .
C20 C 0.1889(15) 0.5298(14) 0.14901(19) 0.028(3) Uani 1 1 d . . .
C21 C 0.1755(15) 0.5114(13) 0.12042(17) 0.025(2) Uani 1 1 d . . .
H21 H 0.2898 0.4666 0.1104 0.030 Uiso 1 1 calc R . .
C22 C -0.0284(14) 0.5690(14) 0.11001(16) 0.024(3) Uani 1 1 d . . .
C23 C -0.1069(15) 0.5653(14) 0.08186(17) 0.024(2) Uani 1 1 d . . .
C24 C 0.0125(17) 0.4820(15) 0.06293(19) 0.039(3) Uani 1 1 d . . .
H24 H 0.1471 0.4259 0.0679 0.047 Uiso 1 1 calc R . .
C25 C -0.0631(18) 0.4794(15) 0.0365(2) 0.041(3) Uani 1 1 d . . .
H25 H 0.0211 0.4224 0.0239 0.049 Uiso 1 1 calc R . .
C26 C -0.2616(16) 0.5606(16) 0.0287(2) 0.040(3) Uani 1 1 d . . .
H26 H -0.3120 0.5592 0.0110 0.048 Uiso 1 1 calc R . .
C27 C -0.3858(17) 0.6440(15) 0.04733(19) 0.038(3) Uani 1 1 d . . .
H27 H -0.5208 0.6988 0.0421 0.046 Uiso 1 1 calc R . .
C28 C -0.3105(17) 0.6467(15) 0.07384(19) 0.037(3) Uani 1 1 d . . .
H28 H -0.3957 0.7028 0.0864 0.044 Uiso 1 1 calc R . .
S1 S 0.2050(4) 0.4883(4) 0.36711(5) 0.0293(7) Uani 1 1 d . . .
S2 S -0.3891(4) 0.6663(4) 0.32825(5) 0.0312(8) Uani 1 1 d . . .
S3 S 0.1707(4) 0.4917(4) 0.28868(5) 0.0300(8) Uani 1 1 d . . .
S4 S -0.1701(4) 0.6470(4) 0.21281(4) 0.0290(7) Uani 1 1 d . . .
S5 S 0.3904(4) 0.4711(4) 0.17343(5) 0.0310(8) Uani 1 1 d . . .
S6 S -0.2036(4) 0.6464(4) 0.13434(5) 0.0309(8) Uani 1 1 d . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C8 1.375(12) . ?
C1 C2 1.476(12) . ?
C1 S1 1.757(9) . ?
C2 C7 1.372(13) . ?
C2 C3 1.394(13) . ?
C3 C4 1.393(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(14) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(14) . ?
C5 H5 0.9300 . ?
C6 C7 1.392(13) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.419(11) . ?
C8 H8 0.9300 . ?
C9 C10 1.408(12) . ?
C9 S2 1.730(9) . ?
C10 C11 1.425(11) . ?
C10 S1 1.728(9) . ?
C11 C12 1.382(12) . ?
C11 S3 1.731(9) . ?
C12 C13 1.411(11) . ?
C12 S2 1.753(9) . ?
C13 C14 1.361(12) . ?
C13 H13 0.9300 . ?
C14 C15 1.443(11) . ?
C14 S3 1.747(8) . ?
C15 C16 1.360(12) . ?
C15 S4 1.764(8) . ?
C16 C17 1.428(12) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(12) . ?
C17 S5 1.759(9) . ?
C18 C19 1.456(11) . ?
C18 S4 1.704(9) . ?
C19 C20 1.381(12) . ?
C19 S6 1.728(9) . ?
C20 C21 1.444(12) . ?
C20 S5 1.734(9) . ?
C21 C22 1.370(12) . ?
C21 H21 0.9300 . ?
C22 C23 1.471(11) . ?
C22 S6 1.748(9) . ?
C23 C24 1.369(13) . ?
C23 C28 1.400(13) . ?
C24 C25 1.386(13) . ?
C24 H24 0.9300 . ?
C25 C26 1.371(13) . ?
C25 H25 0.9300 . ?
C26 C27 1.373(13) . ?
C26 H26 0.9300 . ?
C27 C28 1.388(12) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C1 C2 128.7(9) . . ?
C8 C1 S1 112.3(6) . . ?
C2 C1 S1 119.0(7) . . ?
C7 C2 C3 118.5(9) . . ?
C7 C2 C1 122.4(9) . . ?
C3 C2 C1 119.1(9) . . ?
C2 C3 C4 120.0(10) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.5(10) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 119.4(10) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 119.3(10) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C2 C7 C6 122.3(10) . . ?
C2 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C1 C8 C9 111.8(8) . . ?
C1 C8 H8 124.1 . . ?
C9 C8 H8 124.1 . . ?
C10 C9 C8 113.6(8) . . ?
C10 C9 S2 112.0(6) . . ?
C8 C9 S2 134.4(7) . . ?
C9 C10 C11 111.9(8) . . ?
C9 C10 S1 110.8(7) . . ?
C11 C10 S1 137.1(7) . . ?
C12 C11 C10 112.9(8) . . ?
C12 C11 S3 110.3(7) . . ?
C10 C11 S3 136.4(7) . . ?
C11 C12 C13 114.7(8) . . ?
C11 C12 S2 111.8(7) . . ?
C13 C12 S2 133.3(7) . . ?
C14 C13 C12 111.2(8) . . ?
C14 C13 H13 124.4 . . ?
C12 C13 H13 124.4 . . ?
C13 C14 C15 128.4(7) . . ?
C13 C14 S3 112.7(7) . . ?
C15 C14 S3 118.8(6) . . ?
C16 C15 C14 128.5(8) . . ?
C16 C15 S4 112.3(7) . . ?
C14 C15 S4 119.2(6) . . ?
C15 C16 C17 110.7(8) . . ?
C15 C16 H16 124.6 . . ?
C17 C16 H16 124.6 . . ?
C18 C17 C16 114.3(9) . . ?
C18 C17 S5 113.3(7) . . ?
C16 C17 S5 132.4(7) . . ?
C17 C18 C19 110.9(8) . . ?
C17 C18 S4 111.5(7) . . ?
C19 C18 S4 137.1(7) . . ?
C20 C19 C18 112.5(8) . . ?
C20 C19 S6 111.2(7) . . ?
C18 C19 S6 136.0(7) . . ?
C19 C20 C21 113.8(8) . . ?
C19 C20 S5 112.9(7) . . ?
C21 C20 S5 133.3(7) . . ?
C22 C21 C20 110.9(8) . . ?
C22 C21 H21 124.6 . . ?
C20 C21 H21 124.6 . . ?
C21 C22 C23 126.7(9) . . ?
C21 C22 S6 112.7(7) . . ?
C23 C22 S6 120.6(7) . . ?
C24 C23 C28 118.2(9) . . ?
C24 C23 C22 121.8(9) . . ?
C28 C23 C22 120.0(9) . . ?
C23 C24 C25 121.4(10) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C26 C25 C24 120.1(10) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C27 119.7(9) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C26 C27 C28 120.2(10) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C27 C28 C23 120.4(10) . . ?
C27 C28 H28 119.8 . . ?
C23 C28 H28 119.8 . . ?
C10 S1 C1 91.4(4) . . ?
C9 S2 C12 91.3(4) . . ?
C11 S3 C14 91.0(4) . . ?
C18 S4 C15 91.1(4) . . ?
C20 S5 C17 90.3(5) . . ?
C19 S6 C22 91.4(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.755
_refine_diff_density_min         -0.789
_refine_diff_density_rms         0.271
_database_code_depnum_ccdc_archive 'CCDC 1005153'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_a14202

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H12 S3'
_chemical_formula_sum            'C20 H12 S3'
_chemical_formula_weight         348.48

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.468(4)
_cell_length_b                   5.916(3)
_cell_length_c                   34.719(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.01(4)
_cell_angle_gamma                90.00
_cell_volume                     1530.2(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7619
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8859
_diffrn_reflns_av_R_equivalents  0.1837
_diffrn_reflns_av_sigmaI/netI    0.2492
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         25.12
_reflns_number_total             2642
_reflns_number_gt                1227
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1339P)²+25.2888P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2642
_refine_ls_number_parameters     105
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2708
_refine_ls_R_factor_gt           0.1599
_refine_ls_wR_factor_ref         0.4062
_refine_ls_wR_factor_gt          0.3548
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5200(18) 0.933(3) 0.3436(4) 0.025(3) Uiso 1 1 d . . .
C2 C 0.5289(18) 0.861(3) 0.3839(4) 0.027(3) Uiso 1 1 d . . .
C3 C 0.6136(19) 0.997(3) 0.4132(4) 0.034(4) Uiso 1 1 d . . .
H3 H 0.6680 1.1349 0.4063 0.041 Uiso 1 1 calc R . .
C4 C 0.6198(19) 0.936(3) 0.4513(4) 0.034(4) Uiso 1 1 d . . .
H4 H 0.6775 1.0321 0.4703 0.041 Uiso 1 1 calc R . .
C5 C 0.5419(19) 0.734(3) 0.4625(4) 0.040(4) Uiso 1 1 d . . .
H5 H 0.5459 0.6905 0.4889 0.048 Uiso 1 1 calc R . .
C6 C 0.459(2) 0.598(3) 0.4341(4) 0.039(4) Uiso 1 1 d . . .
H6 H 0.4061 0.4595 0.4411 0.047 Uiso 1 1 calc R . .
C7 C 0.4517(18) 0.661(3) 0.3960(4) 0.030(4) Uiso 1 1 d . . .
H7 H 0.3922 0.5653 0.3772 0.036 Uiso 1 1 calc R . .
C8 C 0.5736(18) 1.133(3) 0.3275(4) 0.030(4) Uiso 1 1 d . . .
H8 H 0.6208 1.2591 0.3418 0.036 Uiso 1 1 calc R . .
C9 C 0.5487(17) 1.123(2) 0.2874(4) 0.023(3) Uiso 1 1 d . . .
C10 C 0.4748(16) 0.930(2) 0.2715(3) 0.019(3) Uiso 1 1 d . . .
C11 C 0.4621(17) 0.931(2) 0.2313(4) 0.022(3) Uiso 1 1 d . . .
C12 C 0.5278(17) 1.125(2) 0.2159(4) 0.022(3) Uiso 1 1 d . . .
C13 C 0.5368(18) 1.128(3) 0.1758(4) 0.031(4) Uiso 1 1 d . . .
H13 H 0.5798 1.2521 0.1618 0.037 Uiso 1 1 calc R . .
C14 C 0.4747(17) 0.926(2) 0.1590(4) 0.024(3) Uiso 1 1 d . . .
C15 C 0.4668(18) 0.857(3) 0.1193(4) 0.026(3) Uiso 1 1 d . . .
C16 C 0.545(2) 0.990(3) 0.0912(4) 0.036(4) Uiso 1 1 d . . .
H16 H 0.6071 1.1252 0.0988 0.043 Uiso 1 1 calc R . .
C17 C 0.534(2) 0.928(3) 0.0531(4) 0.041(4) Uiso 1 1 d . . .
H17 H 0.5845 1.0236 0.0347 0.049 Uiso 1 1 calc R . .
C18 C 0.4507(19) 0.730(3) 0.0409(4) 0.041(4) Uiso 1 1 d . . .
H18 H 0.4445 0.6864 0.0145 0.049 Uiso 1 1 calc R . .
C19 C 0.375(2) 0.595(3) 0.0689(4) 0.037(4) Uiso 1 1 d . . .
H19 H 0.3181 0.4569 0.0612 0.045 Uiso 1 1 calc R . .
C20 C 0.3820(19) 0.656(3) 0.1065(4) 0.036(4) Uiso 1 1 d . . .
H20 H 0.3287 0.5608 0.1246 0.043 Uiso 1 1 calc R . .
S1 S 0.4350(5) 0.7403(7) 0.30799(11) 0.0295(10) Uani 1 1 d . . .
S2 S 0.5978(5) 1.3213(6) 0.25172(12) 0.03424(8) Uani 1 1 d . . .
S3 S 0.4066(5) 0.7375(7) 0.19432(11) 0.0296(10) Uani 1 1 d . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C8 1.38(2) . ?
C1 C2 1.461(18) . ?
C1 S1 1.769(14) . ?
C2 C7 1.39(2) . ?
C2 C3 1.411(19) . ?
C3 C4 1.368(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.40(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.38(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.373(19) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.395(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.370(19) . ?
C9 S2 1.761(14) . ?
C10 C11 1.391(16) . ?
C10 S1 1.734(13) . ?
C11 C12 1.372(19) . ?
C11 S3 1.749(14) . ?
C12 C13 1.399(18) . ?
C12 S2 1.753(13) . ?
C13 C14 1.39(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.434(18) . ?
C14 S3 1.758(14) . ?
C15 C20 1.41(2) . ?
C15 C16 1.41(2) . ?
C16 C17 1.37(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.38(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.41(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.352(19) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C1 C2 130.2(13) . . ?
C8 C1 S1 111.7(10) . . ?
C2 C1 S1 118.1(11) . . ?
C7 C2 C3 116.3(13) . . ?
C7 C2 C1 123.0(13) . . ?
C3 C2 C1 120.7(14) . . ?
C4 C3 C2 121.9(15) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 120.5(15) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 118.2(15) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C7 C6 C5 121.1(17) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C2 122.0(14) . . ?
C6 C7 H7 119.0 . . ?
C2 C7 H7 119.0 . . ?
C1 C8 C9 110.5(13) . . ?
C1 C8 H8 124.8 . . ?
C9 C8 H8 124.8 . . ?
C10 C9 C8 117.2(13) . . ?
C10 C9 S2 111.7(10) . . ?
C8 C9 S2 131.1(12) . . ?
C9 C10 C11 113.5(12) . . ?
C9 C10 S1 109.3(9) . . ?
C11 C10 S1 137.0(11) . . ?
C12 C11 C10 113.1(12) . . ?
C12 C11 S3 109.6(9) . . ?
C10 C11 S3 136.9(12) . . ?
C11 C12 C13 116.2(13) . . ?
C11 C12 S2 112.0(9) . . ?
C13 C12 S2 131.7(12) . . ?
C14 C13 C12 111.6(14) . . ?
C14 C13 H13 124.2 . . ?
C12 C13 H13 124.2 . . ?
C13 C14 C15 129.4(14) . . ?
C13 C14 S3 110.9(10) . . ?
C15 C14 S3 119.7(11) . . ?
C20 C15 C16 116.9(13) . . ?
C20 C15 C14 122.1(13) . . ?
C16 C15 C14 121.1(14) . . ?
C17 C16 C15 121.2(15) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 121.3(16) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C17 C18 C19 117.7(15) . . ?
C17 C18 H18 121.1 . . ?
C19 C18 H18 121.1 . . ?
C20 C19 C18 121.7(17) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C15 121.1(15) . . ?
C19 C20 H20 119.4 . . ?
C15 C20 H20 119.4 . . ?
C10 S1 C1 91.3(7) . . ?
C12 S2 C9 89.5(7) . . ?
C11 S3 C14 91.8(7) . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        25.12
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         1.214
_refine_diff_density_min         -1.465
_refine_diff_density_rms         0.173
_database_code_depnum_ccdc_archive 'CCDC 1005154'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ch14574

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H9 F5 S6'
_chemical_formula_sum            'C28 H9 F5 S6'
_chemical_formula_weight         632.71

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.8338(5)
_cell_length_b                   5.8334(8)
_cell_length_c                   26.039(4)
_cell_angle_alpha                86.150(9)
_cell_angle_beta                 87.916(10)
_cell_angle_gamma                87.044(9)
_cell_volume                     579.93(13)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             318
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8138
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4776
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_sigmaI/netI    0.0899
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         25.06
_reflns_number_total             2031
_reflns_number_gt                1376
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1032P)²+0.6820P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2031
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0692
_refine_ls_wR_factor_ref         0.2001
_refine_ls_wR_factor_gt          0.1767
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9623(14) 0.0220(11) 0.0267(2) 0.0282(14) Uani 1 1 d . . .
C2 C 0.8047(15) 0.2137(11) 0.0468(2) 0.0318(14) Uani 1 1 d . . .
H2 H 0.7225 0.3428 0.0271 0.038 Uiso 1 1 calc R . .
C3 C 0.7824(13) 0.1916(11) 0.1009(2) 0.0271(14) Uani 1 1 d . . .
C4 C 0.9159(14) -0.0170(11) 0.1220(2) 0.0297(14) Uani 1 1 d . . .
C5 C 0.8907(14) -0.0311(11) 0.1768(2) 0.0282(14) Uani 1 1 d . . .
C6 C 0.7364(15) 0.1690(11) 0.1957(2) 0.0306(14) Uani 1 1 d . . .
C7 C 0.7150(15) 0.1611(12) 0.2500(2) 0.0349(15) Uani 1 1 d . . .
H7 H 0.6159 0.2803 0.2685 0.042 Uiso 1 1 calc R . .
C8 C 0.8544(15) -0.0390(12) 0.2727(2) 0.0327(15) Uani 1 1 d . . .
C9 C 0.8726(15) -0.1081(11) 0.3277(2) 0.0299(14) Uani 1 1 d . A .
C10 C 0.7454(18) 0.0389(12) 0.3646(2) 0.0399(17) Uani 1 1 d . . .
C11 C 0.762(2) -0.0212(15) 0.4162(3) 0.0504(19) Uani 1 1 d . A .
C12 C 0.910(2) -0.2293(15) 0.4340(3) 0.0484(19) Uani 1 1 d . . .
C13 C 1.040(2) -0.3788(13) 0.3982(3) 0.0466(18) Uani 1 1 d . A .
C14 C 1.0270(17) -0.3185(13) 0.3467(2) 0.0394(16) Uani 1 1 d . . .
S1 S 1.0788(4) -0.1890(3) 0.07478(6) 0.0315(5) Uani 1 1 d . . .
S2 S 0.6202(4) 0.3742(3) 0.14754(6) 0.0349(5) Uani 1 1 d . . .
S3 S 1.0115(4) -0.2270(3) 0.22617(6) 0.0335(5) Uani 1 1 d . . .
F1 F 0.580(2) 0.2440(14) 0.3501(3) 0.050(2) Uani 0.50 1 d P A 1
F2 F 0.622(2) 0.1263(16) 0.4486(3) 0.060(2) Uani 0.50 1 d P A 1
F3 F 0.930(3) -0.2844(18) 0.4826(3) 0.075(3) Uani 0.50 1 d P A 1
F4 F 1.199(2) -0.5758(15) 0.4130(3) 0.060(2) Uani 0.50 1 d P A 1
F5 F 1.1711(19) -0.4628(13) 0.3132(3) 0.0449(19) Uani 0.50 1 d P A 1
H10 H 0.6423 0.1838 0.3512 0.054 Uiso 0.50 1 d PR A 2
H11 H 0.6741 0.0907 0.4399 0.054 Uiso 0.50 1 d PR A 2
H12 H 0.9187 -0.2523 0.4703 0.054 Uiso 0.50 1 d PR A 2
H13 H 1.1422 -0.5283 0.4101 0.054 Uiso 0.50 1 d PR A 2
H14 H 1.1174 -0.4225 0.3213 0.054 Uiso 0.50 1 d PR A 2


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.370(9) . ?
C1 C1 1.446(12) 2_755 ?
C1 S1 1.749(6) . ?
C2 C3 1.404(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(8) . ?
C3 S2 1.746(6) . ?
C4 C5 1.424(8) . ?
C4 S1 1.719(6) . ?
C5 C6 1.392(9) . ?
C5 S3 1.721(6) . ?
C6 C7 1.412(8) . ?
C6 S2 1.729(6) . ?
C7 C8 1.364(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.465(8) . ?
C8 S3 1.757(6) . ?
C9 C10 1.389(9) . ?
C9 C14 1.402(9) . ?
C10 F1 1.362(10) . ?
C10 C11 1.369(10) . ?
C10 H10 0.9639 . ?
C11 F2 1.326(11) . ?
C11 C12 1.371(11) . ?
C11 H11 0.9676 . ?
C12 F3 1.289(10) . ?
C12 C13 1.381(11) . ?
C12 H12 0.9481 . ?
C13 F4 1.315(11) . ?
C13 C14 1.366(9) . ?
C13 H13 0.9738 . ?
C14 F5 1.338(10) . ?
C14 H14 0.9698 . ?
F1 H10 0.4142 . ?
F2 H11 0.3658 . ?
F3 H12 0.3627 . ?
F4 H13 0.3499 . ?
F5 H14 0.3754 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C1 128.9(7) . 2_755 ?
C2 C1 S1 111.9(5) . . ?
C1 C1 S1 119.2(6) 2_755 . ?
C1 C2 C3 111.8(6) . . ?
C1 C2 H2 124.1 . . ?
C3 C2 H2 124.1 . . ?
C4 C3 C2 114.2(6) . . ?
C4 C3 S2 112.6(4) . . ?
C2 C3 S2 133.2(5) . . ?
C3 C4 C5 112.3(6) . . ?
C3 C4 S1 111.0(4) . . ?
C5 C4 S1 136.7(5) . . ?
C6 C5 C4 111.8(5) . . ?
C6 C5 S3 111.3(4) . . ?
C4 C5 S3 136.9(5) . . ?
C5 C6 C7 112.9(6) . . ?
C5 C6 S2 113.0(5) . . ?
C7 C6 S2 134.1(5) . . ?
C8 C7 C6 113.3(6) . . ?
C8 C7 H7 123.4 . . ?
C6 C7 H7 123.4 . . ?
C7 C8 C9 128.3(6) . . ?
C7 C8 S3 111.1(5) . . ?
C9 C8 S3 120.6(5) . . ?
C10 C9 C14 115.8(6) . . ?
C10 C9 C8 120.9(6) . . ?
C14 C9 C8 123.3(6) . . ?
F1 C10 C11 117.8(7) . . ?
F1 C10 C9 120.2(6) . . ?
C11 C10 C9 121.9(7) . . ?
F1 C10 H10 5.7 . . ?
C11 C10 H10 122.9 . . ?
C9 C10 H10 115.2 . . ?
F2 C11 C12 120.9(7) . . ?
F2 C11 C10 117.7(8) . . ?
C12 C11 C10 121.4(7) . . ?
F2 C11 H11 3.6 . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 117.6 . . ?
F3 C12 C11 121.3(8) . . ?
F3 C12 C13 120.6(9) . . ?
C11 C12 C13 118.0(6) . . ?
F3 C12 H12 6.4 . . ?
C11 C12 H12 115.1 . . ?
C13 C12 H12 126.8 . . ?
F4 C13 C14 118.4(8) . . ?
F4 C13 C12 120.7(7) . . ?
C14 C13 C12 120.8(7) . . ?
F4 C13 H13 4.0 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 119.2 . . ?
F5 C14 C13 119.1(7) . . ?
F5 C14 C9 118.8(6) . . ?
C13 C14 C9 122.1(7) . . ?
F5 C14 H14 3.7 . . ?
C13 C14 H14 121.3 . . ?
C9 C14 H14 116.6 . . ?
C4 S1 C1 91.2(3) . . ?
C6 S2 C3 90.3(3) . . ?
C5 S3 C8 91.5(3) . . ?
C10 F1 H10 13.4 . . ?
C11 F2 H11 9.6 . . ?
C12 F3 H12 16.9 . . ?
C13 F4 H13 11.2 . . ?
C14 F5 H14 9.5 . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.118
_database_code_depnum_ccdc_archive 'CCDC 1005155'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_i13863


#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H7 F5 S3'
_chemical_formula_sum            'C20 H7 F5 S3'
_chemical_formula_weight         438.44

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   5.8734(2)
_cell_length_b                   36.1226(12)
_cell_length_c                   7.4967(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.667(2)
_cell_angle_gamma                90
_cell_volume                     1589.85(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      42.86

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       thin
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_correction_T_min  0.8174
_exptl_absorpt_correction_T_max  0.9793

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_number            30972
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.13
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             3658
_reflns_number_gt                3290
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0478P)²+9.4012P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0009(6)
_refine_ls_number_reflns         3658
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0648
_refine_ls_wR_factor_ref         0.1789
_refine_ls_wR_factor_gt          0.17
_refine_ls_goodness_of_fit_ref   1.251
_refine_ls_restrained_S_all      1.251
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.644
_refine_diff_density_min         -1.017
_refine_diff_density_rms         0.128

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.19240(17) 0.80837(3) 0.79638(14) 0.0132(2) Uani 1 1 d . . .
S2 S 0.77334(17) 0.75424(3) 0.99990(14) 0.0138(2) Uani 1 1 d . . .
S3 S 0.19663(17) 0.69917(3) 0.79654(14) 0.0126(2) Uani 1 1 d . . .
F1 F -0.0149(4) 0.63576(7) 0.6990(4) 0.0172(5) Uani 1 1 d . . .
F2 F -0.1020(4) 0.56406(7) 0.6682(4) 0.0191(6) Uani 1 1 d . . .
F3 F 0.2046(5) 0.51280(7) 0.7894(4) 0.0239(6) Uani 1 1 d . . .
F4 F 0.6068(4) 0.53593(7) 0.9459(4) 0.0211(6) Uani 1 1 d . . .
F5 F 0.6969(4) 0.60692(7) 0.9836(4) 0.0182(6) Uani 1 1 d . . .
C1 C 0.3352(7) 0.88187(12) 0.8404(5) 0.0137(8) Uani 1 1 d . . .
C2 C 0.1247(7) 0.89412(12) 0.7697(6) 0.0172(9) Uani 1 1 d . . .
C3 C 0.0776(8) 0.93164(13) 0.7533(6) 0.0194(9) Uani 1 1 d . . .
C4 C 0.2375(8) 0.95805(12) 0.8061(6) 0.0193(9) Uani 1 1 d . . .
C5 C 0.4480(8) 0.94615(13) 0.8776(6) 0.0196(9) Uani 1 1 d . . .
C6 C 0.4956(7) 0.90885(12) 0.8950(6) 0.0163(8) Uani 1 1 d . . .
C7 C 0.3891(7) 0.84242(12) 0.8619(5) 0.0142(8) Uani 1 1 d . . .
C8 C 0.5877(7) 0.82714(12) 0.9313(6) 0.0146(8) Uani 1 1 d . . .
C9 C 0.5799(7) 0.78829(12) 0.9312(5) 0.0134(8) Uani 1 1 d . . .
C10 C 0.3768(7) 0.77351(11) 0.8616(5) 0.0128(8) Uani 1 1 d . . .
C11 C 0.3775(7) 0.73430(11) 0.8640(6) 0.0132(8) Uani 1 1 d . . .
C12 C 0.5813(7) 0.72004(12) 0.9346(5) 0.0139(8) Uani 1 1 d . . .
C13 C 0.5926(7) 0.68106(12) 0.9348(5) 0.0133(8) Uani 1 1 d . . .
C14 C 0.3961(7) 0.66527(11) 0.8627(5) 0.0121(8) Uani 1 1 d . . .
C15 C 0.3463(7) 0.62585(12) 0.8428(5) 0.0129(8) Uani 1 1 d . . .
C16 C 0.1451(7) 0.61188(12) 0.7631(6) 0.0136(8) Uani 1 1 d . . .
C17 C 0.0965(7) 0.57482(12) 0.7457(6) 0.0153(8) Uani 1 1 d . . .
C18 C 0.2504(7) 0.54870(12) 0.8073(6) 0.0155(8) Uani 1 1 d . . .
C19 C 0.4533(7) 0.56066(12) 0.8869(6) 0.0163(8) Uani 1 1 d . . .
C20 C 0.4967(7) 0.59779(12) 0.9026(5) 0.0132(8) Uani 1 1 d . . .
H2 H 0.022(8) 0.8756(13) 0.726(6) 0.004(11) Uiso 1 1 d . . .
H3 H -0.052(8) 0.9376(12) 0.704(6) 0.002(10) Uiso 1 1 d . . .
H4 H 0.221(8) 0.9851(14) 0.813(6) 0.009(11) Uiso 1 1 d . . .
H5 H 0.584(12) 0.9653(19) 0.930(9) 0.05(2) Uiso 1 1 d . . .
H6 H 0.628(10) 0.9021(15) 0.948(8) 0.022(14) Uiso 1 1 d . . .
H8 H 0.704(9) 0.8420(14) 0.979(7) 0.015(12) Uiso 1 1 d . . .
H13 H 0.720(9) 0.6670(15) 0.984(7) 0.019(13) Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C10 1.722(4) . ?
S1 C7 1.748(4) . ?
S2 C12 1.734(4) . ?
S2 C9 1.742(4) . ?
S3 C11 1.721(4) . ?
S3 C14 1.756(4) . ?
F1 C16 1.353(5) . ?
F2 C17 1.345(5) . ?
F3 C18 1.331(5) . ?
F4 C19 1.335(5) . ?
F5 C20 1.349(5) . ?
C1 C2 1.402(6) . ?
C1 C6 1.408(6) . ?
C1 C7 1.468(6) . ?
C2 C3 1.388(6) . ?
C2 H2 0.96(5) . ?
C3 C4 1.388(6) . ?
C3 H3 0.86(5) . ?
C4 C5 1.401(6) . ?
C4 H4 0.98(5) . ?
C5 C6 1.381(6) . ?
C5 H5 1.12(7) . ?
C6 H6 0.90(6) . ?
C7 C8 1.379(6) . ?
C8 C9 1.404(6) . ?
C8 H8 0.93(5) . ?
C9 C10 1.395(6) . ?
C10 C11 1.417(6) . ?
C11 C12 1.393(6) . ?
C12 C13 1.410(6) . ?
C13 C14 1.383(5) . ?
C13 H13 0.97(6) . ?
C14 C15 1.460(6) . ?
C15 C16 1.403(6) . ?
C15 C20 1.409(6) . ?
C16 C17 1.374(6) . ?
C17 C18 1.377(6) . ?
C18 C19 1.386(6) . ?
C19 C20 1.370(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 S1 C7 91.7(2) . . ?
C12 S2 C9 90.4(2) . . ?
C11 S3 C14 91.7(2) . . ?
C2 C1 C6 117.8(4) . . ?
C2 C1 C7 122.2(4) . . ?
C6 C1 C7 120.0(4) . . ?
C3 C2 C1 120.9(4) . . ?
C3 C2 H2 122(3) . . ?
C1 C2 H2 117(3) . . ?
C4 C3 C2 120.9(4) . . ?
C4 C3 H3 122(3) . . ?
C2 C3 H3 117(3) . . ?
C3 C4 C5 118.7(4) . . ?
C3 C4 H4 129(3) . . ?
C5 C4 H4 112(3) . . ?
C6 C5 C4 120.6(4) . . ?
C6 C5 H5 115(4) . . ?
C4 C5 H5 124(4) . . ?
C5 C6 C1 121.0(4) . . ?
C5 C6 H6 119(4) . . ?
C1 C6 H6 120(4) . . ?
C8 C7 C1 127.4(4) . . ?
C8 C7 S1 111.7(3) . . ?
C1 C7 S1 120.9(3) . . ?
C7 C8 C9 111.9(4) . . ?
C7 C8 H8 121(3) . . ?
C9 C8 H8 127(3) . . ?
C10 C9 C8 114.2(4) . . ?
C10 C9 S2 112.6(3) . . ?
C8 C9 S2 133.2(3) . . ?
C9 C10 C11 112.1(4) . . ?
C9 C10 S1 110.5(3) . . ?
C11 C10 S1 137.4(3) . . ?
C12 C11 C10 112.1(4) . . ?
C12 C11 S3 110.8(3) . . ?
C10 C11 S3 137.0(3) . . ?
C11 C12 C13 114.2(4) . . ?
C11 C12 S2 112.9(3) . . ?
C13 C12 S2 132.9(3) . . ?
C14 C13 C12 111.9(4) . . ?
C14 C13 H13 124(3) . . ?
C12 C13 H13 124(3) . . ?
C13 C14 C15 127.2(4) . . ?
C13 C14 S3 111.4(3) . . ?
C15 C14 S3 121.4(3) . . ?
C16 C15 C20 112.9(4) . . ?
C16 C15 C14 123.9(4) . . ?
C20 C15 C14 123.2(4) . . ?
F1 C16 C17 116.6(4) . . ?
F1 C16 C15 119.3(4) . . ?
C17 C16 C15 124.1(4) . . ?
F2 C17 C16 119.8(4) . . ?
F2 C17 C18 119.9(4) . . ?
C16 C17 C18 120.2(4) . . ?
F3 C18 C17 120.4(4) . . ?
F3 C18 C19 121.0(4) . . ?
C17 C18 C19 118.6(4) . . ?
F4 C19 C20 120.3(4) . . ?
F4 C19 C18 119.9(4) . . ?
C20 C19 C18 119.8(4) . . ?
F5 C20 C19 115.8(4) . . ?
F5 C20 C15 119.8(4) . . ?
C19 C20 C15 124.3(4) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.4(7) . . . . ?
C7 C1 C2 C3 179.1(4) . . . . ?
C1 C2 C3 C4 0.1(7) . . . . ?
C2 C3 C4 C5 -0.4(7) . . . . ?
C3 C4 C5 C6 0.1(7) . . . . ?
C4 C5 C6 C1 0.5(7) . . . . ?
C2 C1 C6 C5 -0.7(7) . . . . ?
C7 C1 C6 C5 -179.4(4) . . . . ?
C2 C1 C7 C8 -179.2(4) . . . . ?
C6 C1 C7 C8 -0.5(7) . . . . ?
C2 C1 C7 S1 1.0(6) . . . . ?
C6 C1 C7 S1 179.6(3) . . . . ?
C10 S1 C7 C8 -0.1(3) . . . . ?
C10 S1 C7 C1 179.8(4) . . . . ?
C1 C7 C8 C9 -179.9(4) . . . . ?
S1 C7 C8 C9 0.0(5) . . . . ?
C7 C8 C9 C10 0.2(5) . . . . ?
C7 C8 C9 S2 180.0(3) . . . . ?
C12 S2 C9 C10 0.1(3) . . . . ?
C12 S2 C9 C8 -179.6(4) . . . . ?
C8 C9 C10 C11 179.8(4) . . . . ?
S2 C9 C10 C11 0.0(5) . . . . ?
C8 C9 C10 S1 -0.3(5) . . . . ?
S2 C9 C10 S1 179.9(2) . . . . ?
C7 S1 C10 C9 0.2(3) . . . . ?
C7 S1 C10 C11 -180.0(5) . . . . ?
C9 C10 C11 C12 -0.2(5) . . . . ?
S1 C10 C11 C12 180.0(4) . . . . ?
C9 C10 C11 S3 -177.8(4) . . . . ?
S1 C10 C11 S3 2.5(8) . . . . ?
C14 S3 C11 C12 -0.2(3) . . . . ?
C14 S3 C11 C10 177.3(5) . . . . ?
C10 C11 C12 C13 -178.2(4) . . . . ?
S3 C11 C12 C13 0.0(5) . . . . ?
C10 C11 C12 S2 0.3(5) . . . . ?
S3 C11 C12 S2 178.5(2) . . . . ?
C9 S2 C12 C11 -0.3(3) . . . . ?
C9 S2 C12 C13 177.9(4) . . . . ?
C11 C12 C13 C14 0.4(5) . . . . ?
S2 C12 C13 C14 -177.8(3) . . . . ?
C12 C13 C14 C15 -179.3(4) . . . . ?
C12 C13 C14 S3 -0.5(5) . . . . ?
C11 S3 C14 C13 0.4(3) . . . . ?
C11 S3 C14 C15 179.3(3) . . . . ?
C13 C14 C15 C16 -178.0(4) . . . . ?
S3 C14 C15 C16 3.3(6) . . . . ?
C13 C14 C15 C20 2.1(7) . . . . ?
S3 C14 C15 C20 -176.6(3) . . . . ?
C20 C15 C16 F1 -179.8(4) . . . . ?
C14 C15 C16 F1 0.3(6) . . . . ?
C20 C15 C16 C17 0.6(6) . . . . ?
C14 C15 C16 C17 -179.3(4) . . . . ?
F1 C16 C17 F2 0.0(6) . . . . ?
C15 C16 C17 F2 179.6(4) . . . . ?
F1 C16 C17 C18 179.9(4) . . . . ?
C15 C16 C17 C18 -0.5(7) . . . . ?
F2 C17 C18 F3 0.5(6) . . . . ?
C16 C17 C18 F3 -179.5(4) . . . . ?
F2 C17 C18 C19 -179.9(4) . . . . ?
C16 C17 C18 C19 0.2(7) . . . . ?
F3 C18 C19 F4 0.4(7) . . . . ?
C17 C18 C19 F4 -179.2(4) . . . . ?
F3 C18 C19 C20 179.6(4) . . . . ?
C17 C18 C19 C20 0.0(7) . . . . ?
F4 C19 C20 F5 -1.6(6) . . . . ?
C18 C19 C20 F5 179.3(4) . . . . ?
F4 C19 C20 C15 179.4(4) . . . . ?
C18 C19 C20 C15 0.2(7) . . . . ?
C16 C15 C20 F5 -179.5(4) . . . . ?
C14 C15 C20 F5 0.4(6) . . . . ?
C16 C15 C20 C19 -0.4(6) . . . . ?
C14 C15 C20 C19 179.5(4) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 1005156'
