# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_mh165_0m
_database_code_depnum_ccdc_archive 'CCDC 1451107'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H10 F10 S2'
_chemical_formula_weight         696.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.5254(3)
_cell_length_b                   12.2658(5)
_cell_length_c                   24.0109(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2805.35(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4574
_cell_measurement_theta_min      3.68
_cell_measurement_theta_max      66.47

_exptl_crystal_description       block
_exptl_crystal_colour            dark-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    2.590
_shelx_estimated_absorpt_T_min   0.713
_shelx_estimated_absorpt_T_max   0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6399
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12847
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.682
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             2481
_reflns_number_gt                2009
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0880P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2481
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1244
_refine_ls_wR_factor_gt          0.1152
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.09025(6) 1.15055(4) 0.49299(2) 0.0372(2) Uani 1 1 d . . . . .
F1 F 0.12356(14) 0.76059(11) 0.40206(6) 0.0495(4) Uani 1 1 d . . . . .
F2 F 0.14947(18) 0.60899(11) 0.32211(6) 0.0651(5) Uani 1 1 d . . . . .
F3 F 0.3695(2) 0.61559(14) 0.25042(6) 0.0758(5) Uani 1 1 d . . . . .
F4 F 0.56104(18) 0.77906(16) 0.25838(6) 0.0723(5) Uani 1 1 d . . . . .
F5 F 0.53589(14) 0.93076(12) 0.33641(5) 0.0495(4) Uani 1 1 d . . . . .
C1 C 0.5562(2) 0.91814(17) 0.46333(8) 0.0311(5) Uani 1 1 d . . . . .
C2 C 0.4192(2) 0.96060(16) 0.45544(8) 0.0312(5) Uani 1 1 d . . . . .
C3 C 0.3657(2) 1.04354(17) 0.49330(8) 0.0306(5) Uani 1 1 d . . . . .
C4 C 0.2243(2) 1.06580(17) 0.47397(8) 0.0311(5) Uani 1 1 d . . . . .
C5 C 0.1942(2) 1.00143(16) 0.42791(8) 0.0317(5) Uani 1 1 d . . . . .
C6 C 0.3155(2) 0.93461(16) 0.41638(8) 0.0312(5) Uani 1 1 d . . . . .
C7 C 0.0570(2) 1.02265(17) 0.40515(8) 0.0346(5) Uani 1 1 d . . . . .
C8 C -0.0127(2) 1.10234(17) 0.43743(10) 0.0366(5) Uani 1 1 d . . . . .
C9 C -0.1498(3) 1.13459(19) 0.42533(12) 0.0460(6) Uani 1 1 d . . . . .
C10 C -0.2154(3) 1.0911(2) 0.37955(12) 0.0540(7) Uani 1 1 d . . . . .
C11 C -0.1468(3) 1.0154(2) 0.34605(12) 0.0535(7) Uani 1 1 d . . . . .
C12 C -0.0122(2) 0.9808(2) 0.35868(11) 0.0420(6) Uani 1 1 d . . . . .
C13 C 0.3287(2) 0.85166(16) 0.37244(8) 0.0316(5) Uani 1 1 d . . . . .
C14 C 0.2320(2) 0.76762(17) 0.36681(9) 0.0373(5) Uani 1 1 d . . . . .
C15 C 0.2454(3) 0.68852(19) 0.32620(10) 0.0453(6) Uani 1 1 d . . . . .
C16 C 0.3566(3) 0.6920(2) 0.28981(9) 0.0492(6) Uani 1 1 d . . . . .
C17 C 0.4531(3) 0.7742(2) 0.29409(10) 0.0462(6) Uani 1 1 d . . . . .
C18 C 0.4390(2) 0.85152(18) 0.33487(9) 0.0370(5) Uani 1 1 d . . . . .
H1 H 0.591(2) 0.8650(17) 0.4390(9) 0.033(6) Uiso 1 1 d . . . . .
H9 H -0.197(2) 1.181(2) 0.4459(10) 0.056(8) Uiso 1 1 d . . . . .
H10 H -0.310(3) 1.112(2) 0.3687(9) 0.051(7) Uiso 1 1 d . . . . .
H11 H -0.193(3) 0.982(2) 0.3134(11) 0.071(9) Uiso 1 1 d . . . . .
H12 H 0.034(3) 0.926(2) 0.3370(10) 0.061(8) Uiso 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
S1 C4 1.709(2) . ?
S1 C8 1.758(2) . ?
F1 C14 1.338(2) . ?
F2 C15 1.340(3) . ?
F3 C16 1.337(3) . ?
F4 C17 1.340(3) . ?
F5 C18 1.341(3) . ?
C1 C3 1.364(3) 5_676 ?
C1 C2 1.417(3) . ?
C2 C6 1.399(3) . ?
C2 C3 1.457(3) . ?
C3 C1 1.364(3) 5_676 ?
C3 C4 1.450(3) . ?
C4 C5 1.389(3) . ?
C5 C7 1.440(3) . ?
C5 C6 1.443(3) . ?
C6 C13 1.471(3) . ?
C7 C12 1.394(3) . ?
C7 C8 1.413(3) . ?
C8 C9 1.395(3) . ?
C9 C10 1.372(4) . ?
C10 C11 1.392(4) . ?
C11 C12 1.384(3) . ?
C13 C18 1.385(3) . ?
C13 C14 1.389(3) . ?
C14 C15 1.382(3) . ?
C15 C16 1.374(4) . ?
C16 C17 1.368(4) . ?
C17 C18 1.370(3) . ?

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
C4 S1 C8 90.54(10) . . ?
C3 C1 C2 118.6(2) 5_676 . ?
C6 C2 C1 130.97(19) . . ?
C6 C2 C3 109.29(18) . . ?
C1 C2 C3 119.71(19) . . ?
C1 C3 C4 133.4(2) 5_676 . ?
C1 C3 C2 121.7(2) 5_676 . ?
C4 C3 C2 104.89(18) . . ?
C5 C4 C3 109.84(18) . . ?
C5 C4 S1 113.87(15) . . ?
C3 C4 S1 136.29(17) . . ?
C4 C5 C7 112.75(18) . . ?
C4 C5 C6 108.08(17) . . ?
C7 C5 C6 139.13(19) . . ?
C2 C6 C5 107.89(17) . . ?
C2 C6 C13 125.32(18) . . ?
C5 C6 C13 126.77(18) . . ?
C12 C7 C8 118.1(2) . . ?
C12 C7 C5 131.8(2) . . ?
C8 C7 C5 110.08(19) . . ?
C9 C8 C7 121.4(2) . . ?
C9 C8 S1 125.8(2) . . ?
C7 C8 S1 112.75(16) . . ?
C10 C9 C8 118.9(2) . . ?
C9 C10 C11 120.6(2) . . ?
C12 C11 C10 120.8(3) . . ?
C11 C12 C7 120.1(2) . . ?
C18 C13 C14 116.04(19) . . ?
C18 C13 C6 122.19(18) . . ?
C14 C13 C6 121.76(19) . . ?
F1 C14 C15 118.2(2) . . ?
F1 C14 C13 119.88(19) . . ?
C15 C14 C13 121.9(2) . . ?
F2 C15 C14 120.0(2) . . ?
F2 C15 C16 120.1(2) . . ?
C14 C15 C16 119.9(2) . . ?
F3 C16 C17 120.5(2) . . ?
F3 C16 C15 119.9(2) . . ?
C17 C16 C15 119.6(2) . . ?
F4 C17 C16 120.0(2) . . ?
F4 C17 C18 120.1(2) . . ?
C16 C17 C18 119.9(2) . . ?
F5 C18 C17 117.0(2) . . ?
F5 C18 C13 120.23(19) . . ?
C17 C18 C13 122.7(2) . . ?

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
C3 C1 C2 C6 -177.7(2) 5_676 . . . ?
C3 C1 C2 C3 0.2(3) 5_676 . . . ?
C6 C2 C3 C1 178.09(19) . . . 5_676 ?
C1 C2 C3 C1 -0.2(3) . . . 5_676 ?
C6 C2 C3 C4 -0.5(2) . . . . ?
C1 C2 C3 C4 -178.77(18) . . . . ?
C1 C3 C4 C5 -178.4(2) 5_676 . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C1 C3 C4 S1 2.5(4) 5_676 . . . ?
C2 C3 C4 S1 -179.13(18) . . . . ?
C8 S1 C4 C5 -0.84(16) . . . . ?
C8 S1 C4 C3 178.2(2) . . . . ?
C3 C4 C5 C7 -177.65(17) . . . . ?
S1 C4 C5 C7 1.7(2) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
S1 C4 C5 C6 179.83(13) . . . . ?
C1 C2 C6 C5 178.8(2) . . . . ?
C3 C2 C6 C5 0.8(2) . . . . ?
C1 C2 C6 C13 0.1(3) . . . . ?
C3 C2 C6 C13 -177.88(18) . . . . ?
C4 C5 C6 C2 -0.8(2) . . . . ?
C7 C5 C6 C2 176.6(2) . . . . ?
C4 C5 C6 C13 177.85(19) . . . . ?
C7 C5 C6 C13 -4.7(4) . . . . ?
C4 C5 C7 C12 177.0(2) . . . . ?
C6 C5 C7 C12 -0.3(4) . . . . ?
C4 C5 C7 C8 -1.8(2) . . . . ?
C6 C5 C7 C8 -179.1(2) . . . . ?
C12 C7 C8 C9 3.4(3) . . . . ?
C5 C7 C8 C9 -177.6(2) . . . . ?
C12 C7 C8 S1 -177.84(16) . . . . ?
C5 C7 C8 S1 1.1(2) . . . . ?
C4 S1 C8 C9 178.5(2) . . . . ?
C4 S1 C8 C7 -0.21(16) . . . . ?
C7 C8 C9 C10 -2.9(3) . . . . ?
S1 C8 C9 C10 178.52(18) . . . . ?
C8 C9 C10 C11 0.6(4) . . . . ?
C9 C10 C11 C12 1.1(4) . . . . ?
C10 C11 C12 C7 -0.6(4) . . . . ?
C8 C7 C12 C11 -1.6(3) . . . . ?
C5 C7 C12 C11 179.6(2) . . . . ?
C2 C6 C13 C18 -53.9(3) . . . . ?
C5 C6 C13 C18 127.6(2) . . . . ?
C2 C6 C13 C14 125.0(2) . . . . ?
C5 C6 C13 C14 -53.4(3) . . . . ?
C18 C13 C14 F1 178.80(18) . . . . ?
C6 C13 C14 F1 -0.2(3) . . . . ?
C18 C13 C14 C15 0.2(3) . . . . ?
C6 C13 C14 C15 -178.86(19) . . . . ?
F1 C14 C15 F2 1.5(3) . . . . ?
C13 C14 C15 F2 -179.82(18) . . . . ?
F1 C14 C15 C16 -178.96(19) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
F2 C15 C16 F3 -0.4(3) . . . . ?
C14 C15 C16 F3 -179.9(2) . . . . ?
F2 C15 C16 C17 179.4(2) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
F3 C16 C17 F4 0.6(4) . . . . ?
C15 C16 C17 F4 -179.2(2) . . . . ?
F3 C16 C17 C18 -179.6(2) . . . . ?
C15 C16 C17 C18 0.6(4) . . . . ?
F4 C17 C18 F5 0.8(3) . . . . ?
C16 C17 C18 F5 -179.1(2) . . . . ?
F4 C17 C18 C13 179.0(2) . . . . ?
C16 C17 C18 C13 -0.8(4) . . . . ?
C14 C13 C18 F5 178.62(19) . . . . ?
C6 C13 C18 F5 -2.4(3) . . . . ?
C14 C13 C18 C17 0.4(3) . . . . ?
C6 C13 C18 C17 179.4(2) . . . . ?

_refine_diff_density_max         0.245
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.047

_shelxl_version_number           2013-4



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_mh166_0m
_database_code_depnum_ccdc_archive 'CCDC 1451108'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H10 F10 S2'
_chemical_formula_weight         696.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.1062(5)
_cell_length_b                   14.1291(6)
_cell_length_c                   14.3389(6)
_cell_angle_alpha                70.677(2)
_cell_angle_beta                 76.199(3)
_cell_angle_gamma                86.760(3)
_cell_volume                     2061.40(16)
_cell_formula_units_Z            3
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    7673
_cell_measurement_theta_min      3.32
_cell_measurement_theta_max      66.34

_exptl_crystal_description       cut-block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_F_000             1044
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    2.643
_shelx_estimated_absorpt_T_min   0.742
_shelx_estimated_absorpt_T_max   0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6650
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27258
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.316
_diffrn_reflns_theta_max         66.646
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.953
_reflns_number_total             7106
_reflns_number_gt                5752
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0708P)²+0.6483P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7106
_refine_ls_number_parameters     709
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1253
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.96941(6) 0.64012(5) 0.13220(4) 0.03625(17) Uani 1 1 d . . . . .
F1 F 1.14682(13) 0.47408(10) 0.12465(10) 0.0387(3) Uani 1 1 d . . . . .
F2 F 1.16491(16) 0.31670(12) 0.05895(11) 0.0493(4) Uani 1 1 d . . . . .
F3 F 1.03877(19) 0.14375(13) 0.17541(15) 0.0616(5) Uani 1 1 d . . . . .
F4 F 0.89407(17) 0.12868(12) 0.36246(14) 0.0597(5) Uani 1 1 d . . . . .
F5 F 0.86822(15) 0.28560(12) 0.42784(11) 0.0485(4) Uani 1 1 d . . . . .
C1 C 1.0114(2) 0.39788(19) 0.50199(18) 0.0330(5) Uani 1 1 d . . . . .
C2 C 1.0002(2) 0.47596(18) 0.41230(17) 0.0319(5) Uani 1 1 d . . . . .
C3 C 0.9905(2) 0.57866(18) 0.41258(18) 0.0321(5) Uani 1 1 d . . . . .
C4 C 0.9829(2) 0.64049(18) 0.31056(18) 0.0316(5) Uani 1 1 d . . . . .
C5 C 0.9891(2) 0.57787(18) 0.25389(17) 0.0317(5) Uani 1 1 d . . . . .
C6 C 0.9994(2) 0.47449(18) 0.31486(18) 0.0313(5) Uani 1 1 d . . . . .
C7 C 0.9642(2) 0.74290(18) 0.25688(18) 0.0343(6) Uani 1 1 d . . . . .
C8 C 0.9546(2) 0.75353(18) 0.15761(18) 0.0351(6) Uani 1 1 d . . . . .
C9 C 0.9332(3) 0.8463(2) 0.0906(2) 0.0438(7) Uani 1 1 d . . . . .
C10 C 0.9200(3) 0.9282(2) 0.1237(2) 0.0489(8) Uani 1 1 d . . . . .
C11 C 0.9293(3) 0.9189(2) 0.2218(2) 0.0470(7) Uani 1 1 d . . . . .
C12 C 0.9526(3) 0.82780(19) 0.2880(2) 0.0397(6) Uani 1 1 d . . . . .
C13 C 1.0082(2) 0.38741(18) 0.28053(18) 0.0303(5) Uani 1 1 d . . . . .
C14 C 1.0815(2) 0.39027(17) 0.18521(18) 0.0306(5) Uani 1 1 d . . . . .
C15 C 1.0922(2) 0.3101(2) 0.14977(19) 0.0360(6) Uani 1 1 d . . . . .
C16 C 1.0291(3) 0.2215(2) 0.2096(2) 0.0418(6) Uani 1 1 d . . . . .
C17 C 0.9566(3) 0.21443(19) 0.3038(2) 0.0419(6) Uani 1 1 d . . . . .
C18 C 0.9460(2) 0.2957(2) 0.33776(19) 0.0364(6) Uani 1 1 d . . . . .
S1A S 0.29350(6) 0.33614(5) 0.37282(4) 0.03783(17) Uani 1 1 d . . . . .
F1A F 0.44167(18) 0.49984(13) 0.38322(12) 0.0538(4) Uani 1 1 d . . . . .
F2A F 0.3877(2) 0.64526(16) 0.46528(14) 0.0738(6) Uani 1 1 d . . . . .
F3A F 0.2894(2) 0.81844(14) 0.36526(15) 0.0739(6) Uani 1 1 d . . . . .
F4A F 0.24589(18) 0.84359(12) 0.17976(15) 0.0617(5) Uani 1 1 d . . . . .
F5A F 0.28768(16) 0.69548(12) 0.10086(12) 0.0484(4) Uani 1 1 d . . . . .
C1A C 0.5040(2) 0.59886(18) 0.00722(18) 0.0304(5) Uani 1 1 d . . . . .
C2A C 0.4482(2) 0.51634(18) 0.09222(18) 0.0306(5) Uani 1 1 d . . . . .
C3A C 0.4461(2) 0.41719(18) 0.08326(18) 0.0291(5) Uani 1 1 d . . . . .
C4A C 0.3882(2) 0.34909(18) 0.18386(18) 0.0308(5) Uani 1 1 d . . . . .
C5A C 0.3621(2) 0.40545(19) 0.24888(18) 0.0320(5) Uani 1 1 d . . . . .
C6A C 0.3943(2) 0.50967(18) 0.19389(17) 0.0310(5) Uani 1 1 d . . . . .
C7A C 0.3479(2) 0.24666(19) 0.23331(19) 0.0330(5) Uani 1 1 d . . . . .
C8A C 0.2928(2) 0.22915(19) 0.33776(19) 0.0359(6) Uani 1 1 d . . . . .
C9A C 0.2428(3) 0.1357(2) 0.4021(2) 0.0446(7) Uani 1 1 d . . . . .
C10A C 0.2476(3) 0.0595(2) 0.3617(2) 0.0507(7) Uani 1 1 d . . . . .
C11A C 0.3006(3) 0.0750(2) 0.2591(2) 0.0492(7) Uani 1 1 d . . . . .
C12A C 0.3511(3) 0.1668(2) 0.1953(2) 0.0402(6) Uani 1 1 d . . . . .
C13A C 0.3675(2) 0.59102(19) 0.23767(18) 0.0329(5) Uani 1 1 d . . . . .
C14A C 0.3885(3) 0.5817(2) 0.33258(19) 0.0400(6) Uani 1 1 d . . . . .
C15A C 0.3612(3) 0.6567(2) 0.3754(2) 0.0480(7) Uani 1 1 d . . . . .
C16A C 0.3121(3) 0.7446(2) 0.3251(2) 0.0488(8) Uani 1 1 d . . . . .
C17A C 0.2908(3) 0.7573(2) 0.2311(2) 0.0454(7) Uani 1 1 d . . . . .
C18A C 0.3163(2) 0.6811(2) 0.18948(19) 0.0365(6) Uani 1 1 d . . . . .
S1B S 0.71362(6) 0.15488(4) 0.12736(4) 0.03623(17) Uani 1 1 d . . . . .
F1B F 0.54136(16) 0.00108(12) 0.11822(11) 0.0470(4) Uani 1 1 d . . . . .
F2B F 0.56687(18) -0.14875(14) 0.04156(12) 0.0558(5) Uani 1 1 d . . . . .
F3B F 0.64552(16) -0.32971(12) 0.14404(13) 0.0515(4) Uani 1 1 d . . . . .
F4B F 0.69254(15) -0.36037(10) 0.32900(12) 0.0463(4) Uani 1 1 d . . . . .
F5B F 0.67598(15) -0.21063(11) 0.40498(10) 0.0407(4) Uani 1 1 d . . . . .
C1B C 0.4840(2) -0.09778(17) 0.49375(17) 0.0289(5) Uani 1 1 d . . . . .
C2B C 0.5458(2) -0.01854(17) 0.40782(17) 0.0284(5) Uani 1 1 d . . . . .
C3B C 0.5593(2) 0.07940(17) 0.41614(17) 0.0280(5) Uani 1 1 d . . . . .
C4B C 0.6193(2) 0.14393(17) 0.31543(17) 0.0281(5) Uani 1 1 d . . . . .
C5B C 0.6408(2) 0.08724(17) 0.25132(17) 0.0299(5) Uani 1 1 d . . . . .
C6B C 0.5969(2) -0.01462(17) 0.30645(17) 0.0288(5) Uani 1 1 d . . . . .
C7B C 0.6601(2) 0.24583(17) 0.26598(17) 0.0284(5) Uani 1 1 d . . . . .
C8B C 0.7158(2) 0.26222(17) 0.16217(18) 0.0303(5) Uani 1 1 d . . . . .
C9B C 0.7629(2) 0.35654(19) 0.09714(19) 0.0358(6) Uani 1 1 d . . . . .
C10B C 0.7539(3) 0.43390(19) 0.1361(2) 0.0373(6) Uani 1 1 d . . . . .
C11B C 0.6993(3) 0.41958(19) 0.2383(2) 0.0373(6) Uani 1 1 d . . . . .
C12B C 0.6524(2) 0.32674(18) 0.30296(19) 0.0319(5) Uani 1 1 d . . . . .
C13B C 0.6064(2) -0.09789(17) 0.26586(17) 0.0303(5) Uani 1 1 d . . . . .
C14B C 0.5808(2) -0.08652(18) 0.17183(18) 0.0332(5) Uani 1 1 d . . . . .
C15B C 0.5935(2) -0.1630(2) 0.13081(19) 0.0375(6) Uani 1 1 d . . . . .
C16B C 0.6323(2) -0.25550(19) 0.1831(2) 0.0363(6) Uani 1 1 d . . . . .
C17B C 0.6563(2) -0.27066(18) 0.27698(19) 0.0348(6) Uani 1 1 d . . . . .
C18B C 0.6445(2) -0.19262(18) 0.31616(17) 0.0312(5) Uani 1 1 d . . . . .
H1 H 1.014(2) 0.3306(19) 0.5036(17) 0.024(6) Uiso 1 1 d . . . . .
H9 H 0.924(3) 0.853(2) 0.026(2) 0.046(8) Uiso 1 1 d . . . . .
H10 H 0.905(3) 0.988(2) 0.080(2) 0.048(8) Uiso 1 1 d . . . . .
H11 H 0.919(3) 0.974(2) 0.244(2) 0.053(9) Uiso 1 1 d . . . . .
H12 H 0.961(3) 0.824(2) 0.353(2) 0.042(8) Uiso 1 1 d . . . . .
H1A H 0.512(3) 0.664(2) 0.011(2) 0.037(7) Uiso 1 1 d . . . . .
H9A H 0.199(3) 0.126(2) 0.474(2) 0.051(8) Uiso 1 1 d . . . . .
H10A H 0.207(3) -0.002(2) 0.400(2) 0.055(9) Uiso 1 1 d . . . . .
H11A H 0.298(3) 0.021(3) 0.235(3) 0.071(11) Uiso 1 1 d . . . . .
H12A H 0.393(3) 0.176(2) 0.126(2) 0.048(8) Uiso 1 1 d . . . . .
H1B H 0.471(2) -0.1625(19) 0.4861(18) 0.028(6) Uiso 1 1 d . . . . .
H9B H 0.797(3) 0.364(2) 0.031(2) 0.052(9) Uiso 1 1 d . . . . .
H10B H 0.785(3) 0.497(2) 0.099(2) 0.050(9) Uiso 1 1 d . . . . .
H11B H 0.698(3) 0.478(2) 0.263(2) 0.048(8) Uiso 1 1 d . . . . .
H12B H 0.614(3) 0.320(2) 0.370(2) 0.036(7) Uiso 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
S1 C5 1.735(2) . ?
S1 C8 1.748(3) . ?
F1 C14 1.341(3) . ?
F2 C15 1.335(3) . ?
F3 C16 1.333(3) . ?
F4 C17 1.342(3) . ?
F5 C18 1.339(3) . ?
C1 C3 1.366(3) 2_766 ?
C1 C2 1.417(3) . ?
C2 C6 1.406(3) . ?
C2 C3 1.450(3) . ?
C3 C1 1.366(3) 2_766 ?
C3 C4 1.454(3) . ?
C4 C5 1.375(3) . ?
C4 C7 1.426(3) . ?
C5 C6 1.447(3) . ?
C6 C13 1.460(3) . ?
C7 C12 1.401(4) . ?
C7 C8 1.411(4) . ?
C8 C9 1.392(4) . ?
C9 C10 1.376(4) . ?
C10 C11 1.397(4) . ?
C11 C12 1.376(4) . ?
C13 C18 1.399(3) . ?
C13 C14 1.403(3) . ?
C14 C15 1.375(3) . ?
C15 C16 1.378(4) . ?
C16 C17 1.372(4) . ?
C17 C18 1.377(4) . ?
S1A C5A 1.728(2) . ?
S1A C8A 1.745(3) . ?
F1A C14A 1.337(3) . ?
F2A C15A 1.345(3) . ?
F3A C16A 1.334(3) . ?
F4A C17A 1.337(3) . ?
F5A C18A 1.331(3) . ?
C1A C3A 1.371(3) 2_665 ?
C1A C2A 1.418(3) . ?
C2A C6A 1.411(3) . ?
C2A C3A 1.451(3) . ?
C3A C1A 1.371(3) 2_665 ?
C3A C4A 1.459(3) . ?
C4A C5A 1.387(3) . ?
C4A C7A 1.428(3) . ?
C5A C6A 1.440(3) . ?
C6A C13A 1.468(3) . ?
C7A C12A 1.401(4) . ?
C7A C8A 1.419(3) . ?
C8A C9A 1.391(4) . ?
C9A C10A 1.374(4) . ?
C10A C11A 1.396(4) . ?
C11A C12A 1.373(4) . ?
C13A C18A 1.395(4) . ?
C13A C14A 1.397(4) . ?
C14A C15A 1.378(4) . ?
C15A C16A 1.371(5) . ?
C16A C17A 1.376(4) . ?
C17A C18A 1.381(4) . ?
S1B C5B 1.733(2) . ?
S1B C8B 1.749(2) . ?
F1B C14B 1.336(3) . ?
F2B C15B 1.330(3) . ?
F3B C16B 1.329(3) . ?
F4B C17B 1.336(3) . ?
F5B C18B 1.340(3) . ?
C1B C3B 1.371(3) 2_656 ?
C1B C2B 1.419(3) . ?
C2B C6B 1.412(3) . ?
C2B C3B 1.447(3) . ?
C3B C1B 1.371(3) 2_656 ?
C3B C4B 1.449(3) . ?
C4B C5B 1.380(3) . ?
C4B C7B 1.424(3) . ?
C5B C6B 1.441(3) . ?
C6B C13B 1.464(3) . ?
C7B C12B 1.401(3) . ?
C7B C8B 1.414(3) . ?
C8B C9B 1.394(3) . ?
C9B C10B 1.372(4) . ?
C10B C11B 1.396(4) . ?
C11B C12B 1.376(3) . ?
C13B C18B 1.391(3) . ?
C13B C14B 1.400(3) . ?
C14B C15B 1.377(4) . ?
C15B C16B 1.378(4) . ?
C16B C17B 1.379(4) . ?
C17B C18B 1.381(3) . ?

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
C5 S1 C8 90.23(12) . . ?
C3 C1 C2 118.9(2) 2_766 . ?
C6 C2 C1 131.4(2) . . ?
C6 C2 C3 109.2(2) . . ?
C1 C2 C3 119.4(2) . . ?
C1 C3 C2 121.7(2) 2_766 . ?
C1 C3 C4 131.9(2) 2_766 . ?
C2 C3 C4 106.4(2) . . ?
C5 C4 C7 113.7(2) . . ?
C5 C4 C3 107.6(2) . . ?
C7 C4 C3 138.6(2) . . ?
C4 C5 C6 110.8(2) . . ?
C4 C5 S1 112.87(18) . . ?
C6 C5 S1 136.0(2) . . ?
C2 C6 C5 106.0(2) . . ?
C2 C6 C13 127.7(2) . . ?
C5 C6 C13 126.3(2) . . ?
C12 C7 C8 119.0(2) . . ?
C12 C7 C4 130.7(2) . . ?
C8 C7 C4 110.2(2) . . ?
C9 C8 C7 121.3(3) . . ?
C9 C8 S1 125.8(2) . . ?
C7 C8 S1 112.95(18) . . ?
C10 C9 C8 118.5(3) . . ?
C9 C10 C11 120.9(3) . . ?
C12 C11 C10 121.0(3) . . ?
C11 C12 C7 119.2(3) . . ?
C18 C13 C14 114.6(2) . . ?
C18 C13 C6 124.0(2) . . ?
C14 C13 C6 121.4(2) . . ?
F1 C14 C15 117.0(2) . . ?
F1 C14 C13 119.6(2) . . ?
C15 C14 C13 123.4(2) . . ?
F2 C15 C14 120.8(2) . . ?
F2 C15 C16 119.7(2) . . ?
C14 C15 C16 119.5(2) . . ?
F3 C16 C17 120.8(2) . . ?
F3 C16 C15 119.7(3) . . ?
C17 C16 C15 119.5(2) . . ?
F4 C17 C16 120.0(2) . . ?
F4 C17 C18 119.8(3) . . ?
C16 C17 C18 120.2(2) . . ?
F5 C18 C17 117.2(2) . . ?
F5 C18 C13 119.9(2) . . ?
C17 C18 C13 122.8(2) . . ?
C5A S1A C8A 90.39(12) . . ?
C3A C1A C2A 118.5(2) 2_665 . ?
C6A C2A C1A 130.9(2) . . ?
C6A C2A C3A 108.7(2) . . ?
C1A C2A C3A 120.3(2) . . ?
C1A C3A C2A 121.2(2) 2_665 . ?
C1A C3A C4A 132.0(2) 2_665 . ?
C2A C3A C4A 106.9(2) . . ?
C5A C4A C7A 112.8(2) . . ?
C5A C4A C3A 107.0(2) . . ?
C7A C4A C3A 140.2(2) . . ?
C4A C5A C6A 110.7(2) . . ?
C4A C5A S1A 113.45(19) . . ?
C6A C5A S1A 135.77(19) . . ?
C2A C6A C5A 106.6(2) . . ?
C2A C6A C13A 128.5(2) . . ?
C5A C6A C13A 124.8(2) . . ?
C12A C7A C8A 118.3(2) . . ?
C12A C7A C4A 131.1(2) . . ?
C8A C7A C4A 110.6(2) . . ?
C9A C8A C7A 121.8(3) . . ?
C9A C8A S1A 125.4(2) . . ?
C7A C8A S1A 112.79(19) . . ?
C10A C9A C8A 118.1(3) . . ?
C9A C10A C11A 121.2(3) . . ?
C12A C11A C10A 121.0(3) . . ?
C11A C12A C7A 119.6(3) . . ?
C18A C13A C14A 115.5(2) . . ?
C18A C13A C6A 122.7(2) . . ?
C14A C13A C6A 121.8(2) . . ?
F1A C14A C15A 117.5(2) . . ?
F1A C14A C13A 120.1(2) . . ?
C15A C14A C13A 122.3(3) . . ?
F2A C15A C16A 119.8(3) . . ?
F2A C15A C14A 119.8(3) . . ?
C16A C15A C14A 120.4(3) . . ?
F3A C16A C15A 120.3(3) . . ?
F3A C16A C17A 120.4(3) . . ?
C15A C16A C17A 119.3(2) . . ?
F4A C17A C16A 120.1(2) . . ?
F4A C17A C18A 119.9(3) . . ?
C16A C17A C18A 120.0(3) . . ?
F5A C18A C17A 117.4(3) . . ?
F5A C18A C13A 120.1(2) . . ?
C17A C18A C13A 122.5(3) . . ?
C5B S1B C8B 90.08(11) . . ?
C3B C1B C2B 118.4(2) 2_656 . ?
C6B C2B C1B 131.0(2) . . ?
C6B C2B C3B 109.0(2) . . ?
C1B C2B C3B 119.9(2) . . ?
C1B C3B C2B 121.6(2) 2_656 . ?
C1B C3B C4B 131.9(2) 2_656 . ?
C2B C3B C4B 106.38(19) . . ?
C5B C4B C7B 113.5(2) . . ?
C5B C4B C3B 107.9(2) . . ?
C7B C4B C3B 138.5(2) . . ?
C4B C5B C6B 110.4(2) . . ?
C4B C5B S1B 113.14(17) . . ?
C6B C5B S1B 136.49(18) . . ?
C2B C6B C5B 106.3(2) . . ?
C2B C6B C13B 127.0(2) . . ?
C5B C6B C13B 126.8(2) . . ?
C12B C7B C8B 118.7(2) . . ?
C12B C7B C4B 131.0(2) . . ?
C8B C7B C4B 110.2(2) . . ?
C9B C8B C7B 121.2(2) . . ?
C9B C8B S1B 125.73(19) . . ?
C7B C8B S1B 113.02(17) . . ?
C10B C9B C8B 118.4(2) . . ?
C9B C10B C11B 121.4(2) . . ?
C12B C11B C10B 120.6(2) . . ?
C11B C12B C7B 119.7(2) . . ?
C18B C13B C14B 115.3(2) . . ?
C18B C13B C6B 122.7(2) . . ?
C14B C13B C6B 122.0(2) . . ?
F1B C14B C15B 117.2(2) . . ?
F1B C14B C13B 120.0(2) . . ?
C15B C14B C13B 122.8(2) . . ?
F2B C15B C14B 120.5(2) . . ?
F2B C15B C16B 119.6(2) . . ?
C14B C15B C16B 119.9(2) . . ?
F3B C16B C15B 120.4(2) . . ?
F3B C16B C17B 120.3(2) . . ?
C15B C16B C17B 119.3(2) . . ?
F4B C17B C16B 119.9(2) . . ?
F4B C17B C18B 120.2(2) . . ?
C16B C17B C18B 119.9(2) . . ?
F5B C18B C17B 116.9(2) . . ?
F5B C18B C13B 120.2(2) . . ?
C17B C18B C13B 122.8(2) . . ?

_refine_diff_density_max         0.315
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.058

_shelxl_version_number           2013-4



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mh132_a
_database_code_depnum_ccdc_archive 'CCDC 1451109'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44.50 H36.50 Cl1.50 S2'
_chemical_formula_weight         688.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.7863(11)
_cell_length_b                   37.373(3)
_cell_length_c                   7.0980(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.313(5)
_cell_angle_gamma                90
_cell_volume                     3598.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2247
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      49.04

_exptl_crystal_description       plate
_exptl_crystal_colour            'royal blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             1444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    2.593
_shelx_estimated_absorpt_T_min   0.800
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7158
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13782
_diffrn_reflns_av_unetI/netI     0.0825
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.364
_diffrn_reflns_theta_max         53.935
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measured_fraction_theta_full 0.617
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_Laue_measured_fraction_full 0.617
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.617
_reflns_number_total             4023
_reflns_number_gt                2714
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1084P)²+8.4172P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4023
_refine_ls_number_parameters     450
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0737
_refine_ls_wR_factor_ref         0.2203
_refine_ls_wR_factor_gt          0.1903
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.033
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.00725(11) 0.49435(4) 0.2453(2) 0.0334(5) Uani 1 1 d . . . . .
S2 S 0.27367(11) 0.49341(4) 0.2662(2) 0.0351(5) Uani 1 1 d . . . . .
C1 C 0.8837(4) 0.48865(14) 0.2463(9) 0.0279(16) Uani 1 1 d . . . . .
C2 C 0.8177(4) 0.45833(15) 0.2459(9) 0.0267(15) Uani 1 1 d . . . . .
C3 C 0.7218(5) 0.47281(15) 0.2332(9) 0.0301(16) Uani 1 1 d . . . . .
C4 C 0.6307(4) 0.45667(15) 0.2474(9) 0.0282(16) Uani 1 1 d . . . . .
H4A H 0.6259 0.4314 0.2580 0.034 Uiso 1 1 calc R U . . .
C5 C 0.5500(4) 0.47754(15) 0.2458(9) 0.0258(15) Uani 1 1 d . . . . .
C6 C 0.4495(4) 0.46843(15) 0.2639(9) 0.0267(15) Uani 1 1 d . . . . .
C7 C 0.3919(4) 0.43733(16) 0.2849(8) 0.0287(16) Uani 1 1 d . . . . .
C8 C 0.4172(5) 0.40131(16) 0.3060(10) 0.0369(18) Uani 1 1 d . . . . .
H8A H 0.4828 0.3940 0.3023 0.044 Uiso 1 1 calc R U . . .
C9 C 0.3480(5) 0.37640(17) 0.3321(11) 0.047(2) Uani 1 1 d . . . . .
H9A H 0.3665 0.3520 0.3496 0.056 Uiso 1 1 calc R U . . .
C10 C 0.2501(5) 0.38656(18) 0.3333(11) 0.047(2) Uani 1 1 d . . . . .
H10A H 0.2026 0.3689 0.3488 0.056 Uiso 1 1 calc R U . . .
C11 C 0.2220(5) 0.42184(16) 0.3122(10) 0.0389(18) Uani 1 1 d . . . . .
H11A H 0.1559 0.4287 0.3147 0.047 Uiso 1 1 calc R U . . .
C12 C 0.2927(5) 0.44748(16) 0.2870(9) 0.0344(17) Uani 1 1 d . . . . .
C13 C 0.3958(4) 0.49978(15) 0.2548(9) 0.0289(16) Uani 1 1 d . . . . .
C14 C 0.4593(4) 0.53027(15) 0.2363(9) 0.0298(16) Uani 1 1 d . . . . .
C15 C 0.5549(4) 0.51624(15) 0.2319(8) 0.0277(16) Uani 1 1 d . . . . .
C16 C 0.6466(4) 0.53264(16) 0.2276(9) 0.0287(16) Uani 1 1 d . . . . .
H16A H 0.6517 0.5580 0.2244 0.034 Uiso 1 1 calc R U . . .
C17 C 0.7280(4) 0.51181(15) 0.2281(8) 0.0267(15) Uani 1 1 d . . . . .
C18 C 0.8310(4) 0.52042(15) 0.2313(9) 0.0279(16) Uani 1 1 d . . . . .
C19 C 0.8910(4) 0.55086(15) 0.2115(9) 0.0283(16) Uani 1 1 d . . . . .
C20 C 0.8662(5) 0.58704(16) 0.1818(9) 0.0345(17) Uani 1 1 d . . . . .
H20A H 0.8004 0.5947 0.1807 0.041 Uiso 1 1 calc R U . . .
C21 C 0.9370(5) 0.61149(17) 0.1541(9) 0.0385(18) Uani 1 1 d . . . . .
H21A H 0.9196 0.6360 0.1333 0.046 Uiso 1 1 calc R U . . .
C22 C 1.0347(5) 0.60065(16) 0.1564(9) 0.0352(18) Uani 1 1 d . . . . .
H22A H 1.0829 0.6178 0.1373 0.042 Uiso 1 1 calc R U . . .
C23 C 1.0608(5) 0.56519(16) 0.1863(9) 0.0341(17) Uani 1 1 d . . . . .
H23A H 1.1269 0.5579 0.1877 0.041 Uiso 1 1 calc R U . . .
C24 C 0.9896(4) 0.54016(15) 0.2146(9) 0.0290(16) Uani 1 1 d . . . . .
C25 C 0.8460(4) 0.42101(15) 0.2534(9) 0.0259(15) Uani 1 1 d . . . . .
C26 C 0.9415(5) 0.41141(16) 0.3464(9) 0.0325(17) Uani 1 1 d . . . . .
H26A H 0.9856 0.4296 0.4028 0.039 Uiso 1 1 calc R U . . .
C27 C 0.9725(5) 0.37615(16) 0.3572(9) 0.0328(17) Uani 1 1 d . . . . .
H27A H 1.0379 0.3708 0.4190 0.039 Uiso 1 1 calc R U . . .
C28 C 0.9117(5) 0.34838(16) 0.2814(9) 0.0327(17) Uani 1 1 d . . . . .
C29 C 0.8159(5) 0.35787(16) 0.1874(9) 0.0340(17) Uani 1 1 d . . . . .
H29A H 0.7716 0.3397 0.1315 0.041 Uiso 1 1 calc R U . . .
C30 C 0.7861(5) 0.39290(16) 0.1758(9) 0.0314(16) Uani 1 1 d . . . . .
H30A H 0.7212 0.3982 0.1114 0.038 Uiso 1 1 calc R U . . .
C31 C 0.9495(5) 0.30976(16) 0.2933(10) 0.0370(17) Uani 1 1 d . . . . .
C32 C 1.0225(5) 0.30595(18) 0.1520(12) 0.055(2) Uani 1 1 d . . . . .
H32A H 0.9881 0.3110 0.0215 0.083 Uiso 1 1 calc R U . . .
H32B H 1.0487 0.2815 0.1583 0.083 Uiso 1 1 calc R U . . .
H32C H 1.0769 0.3229 0.1868 0.083 Uiso 1 1 calc R U . . .
C33 C 1.0033(6) 0.30173(18) 0.4979(12) 0.059(2) Uani 1 1 d . . . . .
H33A H 0.9569 0.3039 0.5870 0.089 Uiso 1 1 calc R U . . .
H33B H 1.0574 0.3188 0.5336 0.089 Uiso 1 1 calc R U . . .
H33C H 1.0298 0.2773 0.5035 0.089 Uiso 1 1 calc R U . . .
C34 C 0.8691(5) 0.28190(16) 0.2390(11) 0.049(2) Uani 1 1 d . . . . .
H34A H 0.8345 0.2864 0.1081 0.073 Uiso 1 1 calc R U . . .
H34B H 0.8223 0.2834 0.3275 0.073 Uiso 1 1 calc R U . . .
H34C H 0.8987 0.2580 0.2464 0.073 Uiso 1 1 calc R U . . .
C35 C 0.4297(4) 0.56788(15) 0.2379(8) 0.0263(15) Uani 1 1 d . . . . .
C36 C 0.3509(5) 0.57796(16) 0.3272(9) 0.0327(16) Uani 1 1 d . . . . .
H36A H 0.3131 0.5599 0.3744 0.039 Uiso 1 1 calc R U . . .
C37 C 0.3272(5) 0.61308(17) 0.3479(10) 0.0395(18) Uani 1 1 d . . . . .
H37A H 0.2741 0.6186 0.4115 0.047 Uiso 1 1 calc R U . . .
C38 C 0.3780(5) 0.64104(17) 0.2791(10) 0.0390(18) Uani 1 1 d . . . . .
C39 C 0.4528(5) 0.63088(17) 0.1782(10) 0.0405(18) Uani 1 1 d . . . . .
H39A H 0.4872 0.6489 0.1227 0.049 Uiso 1 1 calc R U . . .
C40 C 0.4776(5) 0.59545(16) 0.1573(9) 0.0344(17) Uani 1 1 d . . . . .
H40A H 0.5281 0.5897 0.0871 0.041 Uiso 1 1 calc R U . . .
C41 C 0.3583(6) 0.67987(17) 0.3258(12) 0.053(2) Uani 1 1 d . . . . .
C42 C 0.2503(6) 0.68653(19) 0.3190(12) 0.064(2) Uani 1 1 d . . . . .
H42A H 0.2258 0.6705 0.4092 0.096 Uiso 1 1 calc R U . . .
H42B H 0.2143 0.6820 0.1891 0.096 Uiso 1 1 calc R U . . .
H42C H 0.2402 0.7114 0.3541 0.096 Uiso 1 1 calc R U . . .
C43 C 0.4089(8) 0.6868(2) 0.5316(16) 0.112(4) Uani 1 1 d . . . . .
H43A H 0.3840 0.6699 0.6171 0.167 Uiso 1 1 calc R U . . .
H43B H 0.3951 0.7113 0.5678 0.167 Uiso 1 1 calc R U . . .
H43C H 0.4803 0.6836 0.5421 0.167 Uiso 1 1 calc R U . . .
C44 C 0.3940(6) 0.70585(19) 0.1884(15) 0.086(3) Uani 1 1 d . . . . .
H44A H 0.3603 0.7008 0.0574 0.129 Uiso 1 1 calc R U . . .
H44B H 0.4653 0.7031 0.1960 0.129 Uiso 1 1 calc R U . . .
H44C H 0.3796 0.7304 0.2230 0.129 Uiso 1 1 calc R U . . .
C1S C 0.7114(13) 0.7017(5) 0.029(3) 0.073(10) Uiso 0.25 1 d D . P A 1
H1SA H 0.7365 0.6876 -0.0722 0.088 Uiso 0.25 1 calc R U P A 1
C1SA C 0.6848(14) 0.7185(6) 0.147(4) 0.112(15) Uiso 0.25 1 d D . P A 2
H1SB H 0.6610 0.7327 0.2492 0.134 Uiso 0.25 1 calc R U P A 2
Cl1S Cl 0.7062(5) 0.6747(2) 0.2171(14) 0.175(4) Uani 0.5 1 d D . P . .
Cl2S Cl 0.7919(5) 0.7347(3) 0.1040(12) 0.183(4) Uani 0.5 1 d D . P . .
Cl3S Cl 0.5972(5) 0.7190(2) -0.0677(10) 0.146(3) Uani 0.5 1 d D . P . .


_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 C1 1.718(6) . ?
S1 C24 1.737(6) . ?
S2 C13 1.716(6) . ?
S2 C12 1.739(6) . ?
C1 C18 1.386(8) . ?
C1 C2 1.452(8) . ?
C2 C3 1.416(8) . ?
C2 C25 1.446(8) . ?
C3 C4 1.414(8) . ?
C3 C17 1.461(8) . ?
C4 C5 1.357(8) . ?
C4 H4A 0.9500 . ?
C5 C15 1.452(8) . ?
C5 C6 1.455(8) . ?
C6 C13 1.382(8) . ?
C6 C7 1.430(8) . ?
C7 C8 1.392(8) . ?
C7 C12 1.422(8) . ?
C8 C9 1.368(9) . ?
C8 H8A 0.9500 . ?
C9 C10 1.405(9) . ?
C9 H9A 0.9500 . ?
C10 C11 1.375(9) . ?
C10 H10A 0.9500 . ?
C11 C12 1.401(8) . ?
C11 H11A 0.9500 . ?
C13 C14 1.457(8) . ?
C14 C15 1.424(8) . ?
C14 C35 1.464(8) . ?
C15 C16 1.411(8) . ?
C16 C17 1.365(8) . ?
C16 H16A 0.9500 . ?
C17 C18 1.453(8) . ?
C18 C19 1.428(8) . ?
C19 C20 1.402(8) . ?
C19 C24 1.412(8) . ?
C20 C21 1.376(8) . ?
C20 H20A 0.9500 . ?
C21 C22 1.403(9) . ?
C21 H21A 0.9500 . ?
C22 C23 1.380(8) . ?
C22 H22A 0.9500 . ?
C23 C24 1.397(8) . ?
C23 H23A 0.9500 . ?
C25 C30 1.388(8) . ?
C25 C26 1.411(9) . ?
C26 C27 1.383(8) . ?
C26 H26A 0.9500 . ?
C27 C28 1.381(9) . ?
C27 H27A 0.9500 . ?
C28 C29 1.415(9) . ?
C28 C31 1.532(8) . ?
C29 C30 1.370(8) . ?
C29 H29A 0.9500 . ?
C30 H30A 0.9500 . ?
C31 C34 1.519(9) . ?
C31 C33 1.537(10) . ?
C31 C32 1.550(9) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C40 1.400(8) . ?
C35 C36 1.404(8) . ?
C36 C37 1.367(8) . ?
C36 H36A 0.9500 . ?
C37 C38 1.394(9) . ?
C37 H37A 0.9500 . ?
C38 C39 1.409(9) . ?
C38 C41 1.524(9) . ?
C39 C40 1.382(8) . ?
C39 H39A 0.9500 . ?
C40 H40A 0.9500 . ?
C41 C42 1.502(10) . ?
C41 C44 1.520(11) . ?
C41 C43 1.524(12) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C1S Cl2S 1.680(18) . ?
C1S Cl1S 1.688(18) . ?
C1S Cl3S 1.726(18) . ?
C1S H1SA 1.0000 . ?
C1SA Cl2S 1.673(19) . ?
C1SA Cl1S 1.723(19) . ?
C1SA Cl3S 1.767(19) . ?
C1SA H1SB 1.0000 . ?

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
C1 S1 C24 90.3(3) . . ?
C13 S2 C12 90.4(3) . . ?
C18 C1 C2 110.4(5) . . ?
C18 C1 S1 113.5(4) . . ?
C2 C1 S1 135.9(4) . . ?
C3 C2 C25 127.8(5) . . ?
C3 C2 C1 106.2(5) . . ?
C25 C2 C1 126.0(5) . . ?
C4 C3 C2 131.6(5) . . ?
C4 C3 C17 119.0(5) . . ?
C2 C3 C17 109.0(5) . . ?
C5 C4 C3 119.4(5) . . ?
C5 C4 H4A 120.3 . . ?
C3 C4 H4A 120.3 . . ?
C4 C5 C15 121.7(5) . . ?
C4 C5 C6 131.0(5) . . ?
C15 C5 C6 107.2(5) . . ?
C13 C6 C7 113.0(5) . . ?
C13 C6 C5 108.0(5) . . ?
C7 C6 C5 139.0(5) . . ?
C8 C7 C12 118.6(5) . . ?
C8 C7 C6 131.7(6) . . ?
C12 C7 C6 109.7(5) . . ?
C9 C8 C7 120.4(6) . . ?
C9 C8 H8A 119.8 . . ?
C7 C8 H8A 119.8 . . ?
C8 C9 C10 120.7(6) . . ?
C8 C9 H9A 119.6 . . ?
C10 C9 H9A 119.6 . . ?
C11 C10 C9 120.7(6) . . ?
C11 C10 H10A 119.7 . . ?
C9 C10 H10A 119.7 . . ?
C10 C11 C12 118.8(6) . . ?
C10 C11 H11A 120.6 . . ?
C12 C11 H11A 120.6 . . ?
C11 C12 C7 120.7(6) . . ?
C11 C12 S2 126.0(5) . . ?
C7 C12 S2 113.2(5) . . ?
C6 C13 C14 110.0(5) . . ?
C6 C13 S2 113.7(4) . . ?
C14 C13 S2 136.3(5) . . ?
C15 C14 C13 106.7(5) . . ?
C15 C14 C35 127.8(5) . . ?
C13 C14 C35 125.3(5) . . ?
C16 C15 C14 132.6(5) . . ?
C16 C15 C5 119.1(5) . . ?
C14 C15 C5 108.1(5) . . ?
C17 C16 C15 119.5(5) . . ?
C17 C16 H16A 120.3 . . ?
C15 C16 H16A 120.3 . . ?
C16 C17 C18 132.4(5) . . ?
C16 C17 C3 121.2(5) . . ?
C18 C17 C3 106.4(5) . . ?
C1 C18 C19 112.7(5) . . ?
C1 C18 C17 108.0(5) . . ?
C19 C18 C17 139.2(6) . . ?
C20 C19 C24 118.9(5) . . ?
C20 C19 C18 130.8(6) . . ?
C24 C19 C18 110.2(5) . . ?
C21 C20 C19 120.1(6) . . ?
C21 C20 H20A 119.9 . . ?
C19 C20 H20A 119.9 . . ?
C20 C21 C22 120.7(6) . . ?
C20 C21 H21A 119.7 . . ?
C22 C21 H21A 119.7 . . ?
C23 C22 C21 120.2(5) . . ?
C23 C22 H22A 119.9 . . ?
C21 C22 H22A 119.9 . . ?
C22 C23 C24 119.6(6) . . ?
C22 C23 H23A 120.2 . . ?
C24 C23 H23A 120.2 . . ?
C23 C24 C19 120.5(5) . . ?
C23 C24 S1 126.3(5) . . ?
C19 C24 S1 113.2(4) . . ?
C30 C25 C26 115.6(5) . . ?
C30 C25 C2 125.3(6) . . ?
C26 C25 C2 119.0(5) . . ?
C27 C26 C25 121.4(6) . . ?
C27 C26 H26A 119.3 . . ?
C25 C26 H26A 119.3 . . ?
C28 C27 C26 122.3(6) . . ?
C28 C27 H27A 118.8 . . ?
C26 C27 H27A 118.8 . . ?
C27 C28 C29 116.5(6) . . ?
C27 C28 C31 120.7(6) . . ?
C29 C28 C31 122.8(6) . . ?
C30 C29 C28 120.8(6) . . ?
C30 C29 H29A 119.6 . . ?
C28 C29 H29A 119.6 . . ?
C29 C30 C25 123.3(6) . . ?
C29 C30 H30A 118.3 . . ?
C25 C30 H30A 118.3 . . ?
C34 C31 C28 114.0(6) . . ?
C34 C31 C33 108.2(6) . . ?
C28 C31 C33 109.7(5) . . ?
C34 C31 C32 107.6(5) . . ?
C28 C31 C32 107.8(5) . . ?
C33 C31 C32 109.5(6) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C40 C35 C36 116.5(5) . . ?
C40 C35 C14 123.4(5) . . ?
C36 C35 C14 120.0(5) . . ?
C37 C36 C35 121.7(6) . . ?
C37 C36 H36A 119.1 . . ?
C35 C36 H36A 119.1 . . ?
C36 C37 C38 122.5(6) . . ?
C36 C37 H37A 118.7 . . ?
C38 C37 H37A 118.7 . . ?
C37 C38 C39 115.8(6) . . ?
C37 C38 C41 121.2(6) . . ?
C39 C38 C41 122.9(6) . . ?
C40 C39 C38 122.0(6) . . ?
C40 C39 H39A 119.0 . . ?
C38 C39 H39A 119.0 . . ?
C39 C40 C35 121.1(6) . . ?
C39 C40 H40A 119.4 . . ?
C35 C40 H40A 119.4 . . ?
C42 C41 C44 107.9(6) . . ?
C42 C41 C43 106.5(7) . . ?
C44 C41 C43 111.2(8) . . ?
C42 C41 C38 111.4(6) . . ?
C44 C41 C38 112.2(6) . . ?
C43 C41 C38 107.5(6) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C41 C43 H43A 109.5 . . ?
C41 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C41 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C41 C44 H44A 109.5 . . ?
C41 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C41 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
Cl2S C1S Cl1S 107.9(12) . . ?
Cl2S C1S Cl3S 110.8(12) . . ?
Cl1S C1S Cl3S 111.9(12) . . ?
Cl2S C1S H1SA 108.7 . . ?
Cl1S C1S H1SA 108.7 . . ?
Cl3S C1S H1SA 108.7 . . ?
Cl2S C1SA Cl1S 106.6(13) . . ?
Cl2S C1SA Cl3S 109.2(13) . . ?
Cl1S C1SA Cl3S 108.3(13) . . ?
Cl2S C1SA H1SB 110.9 . . ?
Cl1S C1SA H1SB 110.9 . . ?
Cl3S C1SA H1SB 110.9 . . ?

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
C24 S1 C1 C18 -2.3(5) . . . . ?
C24 S1 C1 C2 172.5(7) . . . . ?
C18 C1 C2 C3 -1.0(7) . . . . ?
S1 C1 C2 C3 -175.9(5) . . . . ?
C18 C1 C2 C25 178.0(6) . . . . ?
S1 C1 C2 C25 3.1(11) . . . . ?
C25 C2 C3 C4 8.7(11) . . . . ?
C1 C2 C3 C4 -172.3(6) . . . . ?
C25 C2 C3 C17 -179.6(6) . . . . ?
C1 C2 C3 C17 -0.7(7) . . . . ?
C2 C3 C4 C5 174.4(6) . . . . ?
C17 C3 C4 C5 3.4(9) . . . . ?
C3 C4 C5 C15 -0.7(9) . . . . ?
C3 C4 C5 C6 -177.8(6) . . . . ?
C4 C5 C6 C13 179.4(6) . . . . ?
C15 C5 C6 C13 1.9(7) . . . . ?
C4 C5 C6 C7 -1.8(13) . . . . ?
C15 C5 C6 C7 -179.3(7) . . . . ?
C13 C6 C7 C8 -177.5(6) . . . . ?
C5 C6 C7 C8 3.8(13) . . . . ?
C13 C6 C7 C12 1.1(7) . . . . ?
C5 C6 C7 C12 -177.7(7) . . . . ?
C12 C7 C8 C9 -1.3(10) . . . . ?
C6 C7 C8 C9 177.1(7) . . . . ?
C7 C8 C9 C10 1.6(11) . . . . ?
C8 C9 C10 C11 -1.4(11) . . . . ?
C9 C10 C11 C12 0.8(11) . . . . ?
C10 C11 C12 C7 -0.6(10) . . . . ?
C10 C11 C12 S2 -177.6(5) . . . . ?
C8 C7 C12 C11 0.8(9) . . . . ?
C6 C7 C12 C11 -178.0(6) . . . . ?
C8 C7 C12 S2 178.2(5) . . . . ?
C6 C7 C12 S2 -0.6(7) . . . . ?
C13 S2 C12 C11 177.2(6) . . . . ?
C13 S2 C12 C7 -0.1(5) . . . . ?
C7 C6 C13 C14 179.2(5) . . . . ?
C5 C6 C13 C14 -1.7(7) . . . . ?
C7 C6 C13 S2 -1.2(7) . . . . ?
C5 C6 C13 S2 177.9(4) . . . . ?
C12 S2 C13 C6 0.7(5) . . . . ?
C12 S2 C13 C14 -179.8(7) . . . . ?
C6 C13 C14 C15 0.7(7) . . . . ?
S2 C13 C14 C15 -178.7(5) . . . . ?
C6 C13 C14 C35 -174.9(6) . . . . ?
S2 C13 C14 C35 5.7(10) . . . . ?
C13 C14 C15 C16 -175.6(6) . . . . ?
C35 C14 C15 C16 -0.1(11) . . . . ?
C13 C14 C15 C5 0.5(7) . . . . ?
C35 C14 C15 C5 176.0(6) . . . . ?
C4 C5 C15 C16 -2.5(9) . . . . ?
C6 C5 C15 C16 175.2(5) . . . . ?
C4 C5 C15 C14 -179.2(6) . . . . ?
C6 C5 C15 C14 -1.5(7) . . . . ?
C14 C15 C16 C17 178.6(6) . . . . ?
C5 C15 C16 C17 2.8(9) . . . . ?
C15 C16 C17 C18 -177.5(6) . . . . ?
C15 C16 C17 C3 -0.1(9) . . . . ?
C4 C3 C17 C16 -3.1(9) . . . . ?
C2 C3 C17 C16 -176.0(6) . . . . ?
C4 C3 C17 C18 174.9(5) . . . . ?
C2 C3 C17 C18 2.0(7) . . . . ?
C2 C1 C18 C19 -174.0(5) . . . . ?
S1 C1 C18 C19 2.1(7) . . . . ?
C2 C1 C18 C17 2.2(7) . . . . ?
S1 C1 C18 C17 178.4(4) . . . . ?
C16 C17 C18 C1 175.1(6) . . . . ?
C3 C17 C18 C1 -2.5(7) . . . . ?
C16 C17 C18 C19 -10.2(13) . . . . ?
C3 C17 C18 C19 172.2(7) . . . . ?
C1 C18 C19 C20 175.9(6) . . . . ?
C17 C18 C19 C20 1.4(12) . . . . ?
C1 C18 C19 C24 -0.6(7) . . . . ?
C17 C18 C19 C24 -175.2(7) . . . . ?
C24 C19 C20 C21 0.7(9) . . . . ?
C18 C19 C20 C21 -175.6(6) . . . . ?
C19 C20 C21 C22 -0.4(10) . . . . ?
C20 C21 C22 C23 0.1(10) . . . . ?
C21 C22 C23 C24 -0.1(9) . . . . ?
C22 C23 C24 C19 0.4(9) . . . . ?
C22 C23 C24 S1 177.4(5) . . . . ?
C20 C19 C24 C23 -0.7(9) . . . . ?
C18 C19 C24 C23 176.3(5) . . . . ?
C20 C19 C24 S1 -178.1(5) . . . . ?
C18 C19 C24 S1 -1.1(7) . . . . ?
C1 S1 C24 C23 -175.3(6) . . . . ?
C1 S1 C24 C19 1.9(5) . . . . ?
C3 C2 C25 C30 27.4(10) . . . . ?
C1 C2 C25 C30 -151.3(6) . . . . ?
C3 C2 C25 C26 -152.4(6) . . . . ?
C1 C2 C25 C26 28.8(9) . . . . ?
C30 C25 C26 C27 0.3(9) . . . . ?
C2 C25 C26 C27 -179.8(5) . . . . ?
C25 C26 C27 C28 -1.2(9) . . . . ?
C26 C27 C28 C29 1.3(9) . . . . ?
C26 C27 C28 C31 178.9(5) . . . . ?
C27 C28 C29 C30 -0.7(9) . . . . ?
C31 C28 C29 C30 -178.2(5) . . . . ?
C28 C29 C30 C25 0.0(10) . . . . ?
C26 C25 C30 C29 0.3(9) . . . . ?
C2 C25 C30 C29 -179.6(6) . . . . ?
C27 C28 C31 C34 168.7(6) . . . . ?
C29 C28 C31 C34 -13.9(9) . . . . ?
C27 C28 C31 C33 47.2(8) . . . . ?
C29 C28 C31 C33 -135.4(6) . . . . ?
C27 C28 C31 C32 -72.0(8) . . . . ?
C29 C28 C31 C32 105.4(7) . . . . ?
C15 C14 C35 C40 27.9(10) . . . . ?
C13 C14 C35 C40 -157.4(6) . . . . ?
C15 C14 C35 C36 -150.7(6) . . . . ?
C13 C14 C35 C36 24.0(9) . . . . ?
C40 C35 C36 C37 -5.1(9) . . . . ?
C14 C35 C36 C37 173.6(6) . . . . ?
C35 C36 C37 C38 1.2(10) . . . . ?
C36 C37 C38 C39 3.0(10) . . . . ?
C36 C37 C38 C41 -172.3(6) . . . . ?
C37 C38 C39 C40 -3.3(10) . . . . ?
C41 C38 C39 C40 171.9(7) . . . . ?
C38 C39 C40 C35 -0.6(10) . . . . ?
C36 C35 C40 C39 4.7(9) . . . . ?
C14 C35 C40 C39 -173.9(6) . . . . ?
C37 C38 C41 C42 -39.9(9) . . . . ?
C39 C38 C41 C42 145.1(7) . . . . ?
C37 C38 C41 C44 -161.0(7) . . . . ?
C39 C38 C41 C44 24.1(10) . . . . ?
C37 C38 C41 C43 76.4(9) . . . . ?
C39 C38 C41 C43 -98.5(9) . . . . ?
Cl2S C1S Cl1S C1SA 60.4(15) . . . . ?
Cl3S C1S Cl1S C1SA -61.8(15) . . . . ?
Cl2S C1SA Cl1S C1S -60.1(15) . . . . ?
Cl3S C1SA Cl1S C1S 57.3(14) . . . . ?
Cl1S C1SA Cl2S C1S 59.1(14) . . . . ?
Cl3S C1SA Cl2S C1S -57.7(15) . . . . ?
Cl1S C1S Cl2S C1SA -61.8(15) . . . . ?
Cl3S C1S Cl2S C1SA 61.0(15) . . . . ?
Cl2S C1S Cl3S C1SA -59.1(15) . . . . ?
Cl1S C1S Cl3S C1SA 61.3(15) . . . . ?
Cl2S C1SA Cl3S C1S 58.6(15) . . . . ?
Cl1S C1SA Cl3S C1S -57.1(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1SA H1SB Cl3S 1.00 2.48 3.45(3) 163.9 4_576

_refine_diff_density_max         0.713
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.076

_shelxl_version_number           2013-4



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_mh125_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1451110'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H52 S2 Si2'
_chemical_formula_weight         725.17

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'
Si Si 0.0817 0.0704 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.041(3)
_cell_length_b                   11.320(4)
_cell_length_c                   12.549(5)
_cell_angle_alpha                106.204(11)
_cell_angle_beta                 106.976(9)
_cell_angle_gamma                99.176(11)
_cell_volume                     1012.3(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1730
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      25.37

_exptl_crystal_description       needle
_exptl_crystal_colour            'deep green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_F_000             388
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.222
_shelx_estimated_absorpt_T_min   0.7239
_shelx_estimated_absorpt_T_max   1.0000
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7239
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13155
_diffrn_reflns_av_unetI/netI     0.1610
_diffrn_reflns_av_R_equivalents  0.1167
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.808
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.925
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.925
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.925
_reflns_number_total             3395
_reflns_number_gt                1793
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0600P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3395
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1488
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.1460
_refine_ls_wR_factor_gt          0.1233
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.27692(16) 0.81372(13) 0.16883(10) 0.0254(4) Uani 1 1 d . . . . .
S1 S 0.56176(14) 0.57811(13) 0.71325(9) 0.0256(4) Uani 1 1 d . . . . .
C1 C -0.0741(5) 0.5411(4) 0.4012(3) 0.0226(11) Uani 1 1 d . . . . .
H1A H -0.1218 0.5681 0.3360 0.027 Uiso 1 1 calc R U . . .
C2 C 0.1132(5) 0.5753(4) 0.4651(3) 0.0211(11) Uani 1 1 d . . . . .
C3 C 0.2572(5) 0.6480(4) 0.4486(3) 0.0223(11) Uani 1 1 d . . . . .
C4 C 0.4216(5) 0.6524(4) 0.5379(3) 0.0192(10) Uani 1 1 d . . . . .
C5 C 0.3772(5) 0.5836(4) 0.6055(3) 0.0180(11) Uani 1 1 d . . . . .
C6 C 0.1845(5) 0.5324(4) 0.5634(3) 0.0210(11) Uani 1 1 d . . . . .
C7 C 0.6113(5) 0.7048(4) 0.5728(3) 0.0230(11) Uani 1 1 d . . . . .
C8 C 0.7056(5) 0.6718(4) 0.6689(3) 0.0228(11) Uani 1 1 d . . . . .
C9 C 0.8932(6) 0.7091(5) 0.7177(4) 0.0291(12) Uani 1 1 d . . . . .
H9A H 0.9556 0.6852 0.7818 0.035 Uiso 1 1 calc R U . . .
C10 C 0.9859(6) 0.7807(5) 0.6719(4) 0.0326(13) Uani 1 1 d . . . . .
H10A H 1.1137 0.8075 0.7051 0.039 Uiso 1 1 calc R U . . .
C11 C 0.8958(6) 0.8150(5) 0.5773(4) 0.0319(12) Uani 1 1 d . . . . .
H11A H 0.9626 0.8647 0.5464 0.038 Uiso 1 1 calc R U . . .
C12 C 0.7087(6) 0.7774(5) 0.5275(4) 0.0270(12) Uani 1 1 d . . . . .
H12A H 0.6478 0.8012 0.4628 0.032 Uiso 1 1 calc R U . . .
C13 C 0.2472(5) 0.7044(4) 0.3599(4) 0.0210(11) Uani 1 1 d . . . . .
C14 C 0.2488(5) 0.7513(5) 0.2850(4) 0.0241(11) Uani 1 1 d . . . . .
C15 C 0.0463(6) 0.8040(5) 0.0685(4) 0.0317(13) Uani 1 1 d . . . . .
H15A H 0.0611 0.8267 -0.0002 0.038 Uiso 1 1 calc R U . . .
C16 C -0.0397(7) 0.9003(6) 0.1300(4) 0.0521(16) Uani 1 1 d . . . . .
H16A H -0.1593 0.8926 0.0750 0.078 Uiso 1 1 calc R U . . .
H16B H 0.0364 0.9868 0.1541 0.078 Uiso 1 1 calc R U . . .
H16C H -0.0513 0.8833 0.2002 0.078 Uiso 1 1 calc R U . . .
C17 C -0.0766(6) 0.6688(5) 0.0185(4) 0.0416(15) Uani 1 1 d . . . . .
H17A H -0.1952 0.6672 -0.0335 0.062 Uiso 1 1 calc R U . . .
H17B H -0.0896 0.6416 0.0839 0.062 Uiso 1 1 calc R U . . .
H17C H -0.0237 0.6107 -0.0270 0.062 Uiso 1 1 calc R U . . .
C18 C 0.4141(6) 0.9836(5) 0.2440(4) 0.0310(12) Uani 1 1 d . . . . .
H18A H 0.3396 1.0299 0.2829 0.037 Uiso 1 1 calc R U . . .
C19 C 0.5910(6) 1.0046(5) 0.3435(4) 0.0442(14) Uani 1 1 d . . . . .
H19A H 0.6540 1.0955 0.3778 0.066 Uiso 1 1 calc R U . . .
H19B H 0.6668 0.9561 0.3115 0.066 Uiso 1 1 calc R U . . .
H19C H 0.5658 0.9756 0.4052 0.066 Uiso 1 1 calc R U . . .
C20 C 0.4445(7) 1.0481(6) 0.1565(4) 0.0575(17) Uani 1 1 d . . . . .
H20A H 0.5165 1.1364 0.2005 0.086 Uiso 1 1 calc R U . . .
H20B H 0.3279 1.0473 0.1025 0.086 Uiso 1 1 calc R U . . .
H20C H 0.5084 1.0019 0.1106 0.086 Uiso 1 1 calc R U . . .
C21 C 0.3823(7) 0.7008(6) 0.0859(4) 0.0515(17) Uani 1 1 d . . . . .
H21A H 0.2924 0.6173 0.0613 0.062 Uiso 1 1 calc R U . . .
C22 C 0.5457(7) 0.6773(6) 0.1570(5) 0.0600(18) Uani 1 1 d . . . . .
H22A H 0.5880 0.6175 0.1046 0.090 Uiso 1 1 calc R U . . .
H22B H 0.5186 0.6407 0.2141 0.090 Uiso 1 1 calc R U . . .
H22C H 0.6396 0.7578 0.1997 0.090 Uiso 1 1 calc R U . . .
C23 C 0.3769(7) 0.7086(6) -0.0312(4) 0.0556(17) Uani 1 1 d . . . . .
H23A H 0.4343 0.6464 -0.0672 0.083 Uiso 1 1 calc R U . . .
H23B H 0.4415 0.7946 -0.0205 0.083 Uiso 1 1 calc R U . . .
H23C H 0.2513 0.6899 -0.0833 0.083 Uiso 1 1 calc R U . . .


_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
Si1 C14 1.842(4) . ?
Si1 C18 1.873(5) . ?
Si1 C15 1.879(4) . ?
Si1 C21 1.885(5) . ?
S1 C5 1.714(4) . ?
S1 C8 1.756(4) . ?
C1 C6 1.371(6) 2_566 ?
C1 C2 1.413(5) . ?
C1 H1A 0.9500 . ?
C2 C3 1.411(6) . ?
C2 C6 1.448(5) . ?
C3 C13 1.418(6) . ?
C3 C4 1.445(5) . ?
C4 C5 1.382(5) . ?
C4 C7 1.430(6) . ?
C5 C6 1.442(5) . ?
C6 C1 1.371(6) 2_566 ?
C7 C12 1.389(6) . ?
C7 C8 1.405(5) . ?
C8 C9 1.394(5) . ?
C9 C10 1.364(6) . ?
C9 H9A 0.9500 . ?
C10 C11 1.389(6) . ?
C10 H10A 0.9500 . ?
C11 C12 1.391(6) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C14 1.205(5) . ?
C15 C17 1.527(7) . ?
C15 C16 1.532(6) . ?
C15 H15A 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.526(6) . ?
C18 C20 1.532(6) . ?
C18 H18A 1.0000 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.468(6) . ?
C21 C23 1.485(6) . ?
C21 H21A 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
C14 Si1 C18 107.6(2) . . ?
C14 Si1 C15 107.60(19) . . ?
C18 Si1 C15 110.6(2) . . ?
C14 Si1 C21 104.6(2) . . ?
C18 Si1 C21 115.9(2) . . ?
C15 Si1 C21 110.1(2) . . ?
C5 S1 C8 90.63(19) . . ?
C6 C1 C2 117.6(3) 2_566 . ?
C6 C1 H1A 121.2 2_566 . ?
C2 C1 H1A 121.2 . . ?
C3 C2 C1 130.1(4) . . ?
C3 C2 C6 109.2(3) . . ?
C1 C2 C6 120.7(4) . . ?
C2 C3 C13 127.5(4) . . ?
C2 C3 C4 107.2(3) . . ?
C13 C3 C4 125.3(4) . . ?
C5 C4 C7 113.5(3) . . ?
C5 C4 C3 108.3(3) . . ?
C7 C4 C3 138.1(4) . . ?
C4 C5 C6 110.0(3) . . ?
C4 C5 S1 113.1(3) . . ?
C6 C5 S1 136.9(3) . . ?
C1 C6 C5 133.0(4) 2_566 . ?
C1 C6 C2 121.7(4) 2_566 . ?
C5 C6 C2 105.3(4) . . ?
C12 C7 C8 118.7(4) . . ?
C12 C7 C4 131.1(4) . . ?
C8 C7 C4 110.2(4) . . ?
C9 C8 C7 121.3(4) . . ?
C9 C8 S1 126.1(3) . . ?
C7 C8 S1 112.6(3) . . ?
C10 C9 C8 118.9(4) . . ?
C10 C9 H9A 120.5 . . ?
C8 C9 H9A 120.5 . . ?
C9 C10 C11 120.9(4) . . ?
C9 C10 H10A 119.6 . . ?
C11 C10 H10A 119.6 . . ?
C10 C11 C12 120.6(4) . . ?
C10 C11 H11A 119.7 . . ?
C12 C11 H11A 119.7 . . ?
C7 C12 C11 119.6(4) . . ?
C7 C12 H12A 120.2 . . ?
C11 C12 H12A 120.2 . . ?
C14 C13 C3 176.1(4) . . ?
C13 C14 Si1 172.2(3) . . ?
C17 C15 C16 111.4(4) . . ?
C17 C15 Si1 111.7(3) . . ?
C16 C15 Si1 111.9(3) . . ?
C17 C15 H15A 107.2 . . ?
C16 C15 H15A 107.2 . . ?
Si1 C15 H15A 107.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C20 111.1(4) . . ?
C19 C18 Si1 114.8(3) . . ?
C20 C18 Si1 112.9(3) . . ?
C19 C18 H18A 105.7 . . ?
C20 C18 H18A 105.7 . . ?
Si1 C18 H18A 105.7 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C23 116.4(4) . . ?
C22 C21 Si1 116.8(3) . . ?
C23 C21 Si1 115.7(4) . . ?
C22 C21 H21A 101.3 . . ?
C23 C21 H21A 101.3 . . ?
Si1 C21 H21A 101.3 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
_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 179.4(5) 2_566 . . . ?
C6 C1 C2 C6 0.8(7) 2_566 . . . ?
C1 C2 C3 C13 -0.9(8) . . . . ?
C6 C2 C3 C13 177.9(4) . . . . ?
C1 C2 C3 C4 -179.3(4) . . . . ?
C6 C2 C3 C4 -0.5(5) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C13 C3 C4 C5 -178.1(4) . . . . ?
C2 C3 C4 C7 178.9(5) . . . . ?
C13 C3 C4 C7 0.5(8) . . . . ?
C7 C4 C5 C6 -179.0(4) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
C7 C4 C5 S1 -0.4(5) . . . . ?
C3 C4 C5 S1 178.6(3) . . . . ?
C8 S1 C5 C4 0.4(3) . . . . ?
C8 S1 C5 C6 178.5(5) . . . . ?
C4 C5 C6 C1 179.9(5) . . . 2_566 ?
S1 C5 C6 C1 1.8(8) . . . 2_566 ?
C4 C5 C6 C2 -0.3(5) . . . . ?
S1 C5 C6 C2 -178.4(4) . . . . ?
C3 C2 C6 C1 -179.7(4) . . . 2_566 ?
C1 C2 C6 C1 -0.8(7) . . . 2_566 ?
C3 C2 C6 C5 0.5(5) . . . . ?
C1 C2 C6 C5 179.4(4) . . . . ?
C5 C4 C7 C12 179.3(5) . . . . ?
C3 C4 C7 C12 0.8(9) . . . . ?
C5 C4 C7 C8 0.1(5) . . . . ?
C3 C4 C7 C8 -178.4(5) . . . . ?
C12 C7 C8 C9 -0.8(6) . . . . ?
C4 C7 C8 C9 178.6(4) . . . . ?
C12 C7 C8 S1 -179.1(4) . . . . ?
C4 C7 C8 S1 0.2(5) . . . . ?
C5 S1 C8 C9 -178.6(4) . . . . ?
C5 S1 C8 C7 -0.4(3) . . . . ?
C7 C8 C9 C10 1.0(7) . . . . ?
S1 C8 C9 C10 179.1(4) . . . . ?
C8 C9 C10 C11 -0.7(7) . . . . ?
C9 C10 C11 C12 0.2(7) . . . . ?
C8 C7 C12 C11 0.3(7) . . . . ?
C4 C7 C12 C11 -178.9(4) . . . . ?
C10 C11 C12 C7 0.0(7) . . . . ?
C14 Si1 C15 C17 -55.4(3) . . . . ?
C18 Si1 C15 C17 -172.6(3) . . . . ?
C21 Si1 C15 C17 58.0(4) . . . . ?
C14 Si1 C15 C16 70.3(4) . . . . ?
C18 Si1 C15 C16 -47.0(4) . . . . ?
C21 Si1 C15 C16 -176.4(4) . . . . ?
C14 Si1 C18 C19 52.4(3) . . . . ?
C15 Si1 C18 C19 169.7(3) . . . . ?
C21 Si1 C18 C19 -64.1(4) . . . . ?
C14 Si1 C18 C20 -178.8(3) . . . . ?
C15 Si1 C18 C20 -61.6(4) . . . . ?
C21 Si1 C18 C20 64.6(4) . . . . ?
C14 Si1 C21 C22 -52.5(5) . . . . ?
C18 Si1 C21 C22 65.7(5) . . . . ?
C15 Si1 C21 C22 -167.8(4) . . . . ?
C14 Si1 C21 C23 164.8(4) . . . . ?
C18 Si1 C21 C23 -76.9(4) . . . . ?
C15 Si1 C21 C23 49.5(5) . . . . ?

_refine_diff_density_max         0.395
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.068

_shelxl_version_number           2013-4



