# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_3a
_audit_block_doi                 10.5517/ccdc.csd.cc20cjmk
_database_code_depnum_ccdc_archive 'CCDC 1858128'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.orglett.8b03169 2018
loop_
_audit_author_name
_audit_author_address
'Yosuke Tani'
;Osaka University
Japan
;
_audit_update_record             
;
2018-07-31 deposited with the CCDC.	2021-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H8 O4'
_chemical_formula_weight         264.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   5.8777(12)
_cell_length_b                   5.7800(12)
_cell_length_c                   16.704(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.63(3)
_cell_angle_gamma                90
_cell_volume                     566.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    5221
_cell_measurement_theta_min      3.475
_cell_measurement_theta_max      27.495

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_F_000             272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6635
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'Rigaku VariMax RAPID FR-E'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5368
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.473
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1299
_reflns_number_gt                1175
_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       'Rigaku RAPID AUTO'
_computing_cell_refinement       'Rigaku RAPID AUTO'
_computing_data_reduction        'Rigaku RAPID AUTO'
_computing_structure_solution    Yadokari-SG
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_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)+(0.0499P)²+0.2945P] 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         1299
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1235
_refine_ls_wR_factor_gt          0.1192
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_restrained_S_all      1.155
_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
O1 O 0.22572(18) 0.1220(2) 0.46555(7) 0.0284(3) Uani 1 1 d . . . . .
O2 O 1.0239(2) -0.0269(2) 0.63289(8) 0.0378(4) Uani 1 1 d . . . . .
C1 C 0.4876(3) 0.2495(3) 0.57194(9) 0.0262(4) Uani 1 1 d . . . . .
C2 C 0.3506(3) 0.4363(3) 0.59122(10) 0.0299(4) Uani 1 1 d . . . . .
H2 H 0.2118 0.4611 0.5626 0.036 Uiso 1 1 calc R U . . .
C3 C 0.4214(3) 0.5836(3) 0.65268(10) 0.0333(4) Uani 1 1 d . . . . .
H3 H 0.3296 0.7077 0.6653 0.040 Uiso 1 1 calc R U . . .
C4 C 0.6291(3) 0.5490(3) 0.69619(10) 0.0334(4) Uani 1 1 d . . . . .
H4 H 0.6748 0.6496 0.7376 0.040 Uiso 1 1 calc R U . . .
C5 C 0.7667(3) 0.3661(3) 0.67786(10) 0.0305(4) Uani 1 1 d . . . . .
H5 H 0.9053 0.3431 0.7068 0.037 Uiso 1 1 calc R U . . .
C6 C 0.6973(3) 0.2149(3) 0.61564(9) 0.0268(4) Uani 1 1 d . . . . .
C7 C 0.4303(3) 0.0871(3) 0.50869(9) 0.0260(4) Uani 1 1 d . . . . .
C8 C 0.8454(3) 0.0199(3) 0.59771(10) 0.0275(4) 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
O1 C7 1.3768(18) . ?
O1 C8 1.381(2) 3_656 ?
O2 C8 1.2006(19) . ?
C1 C2 1.397(2) . ?
C1 C6 1.406(2) . ?
C1 C7 1.438(2) . ?
C2 C3 1.378(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.395(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(2) . ?
C5 H5 0.9300 . ?
C6 C8 1.467(2) . ?
C7 C7 1.341(3) 3_656 ?
C8 O1 1.381(2) 3_656 ?

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
C7 O1 C8 121.69(13) . 3_656 ?
C2 C1 C6 119.30(15) . . ?
C2 C1 C7 124.23(14) . . ?
C6 C1 C7 116.47(15) . . ?
C3 C2 C1 119.88(15) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 120.83(16) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 120.06(16) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 119.82(15) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 120.12(16) . . ?
C5 C6 C8 118.87(14) . . ?
C1 C6 C8 121.02(15) . . ?
C7 C7 O1 121.48(19) 3_656 . ?
C7 C7 C1 122.07(18) 3_656 . ?
O1 C7 C1 116.44(14) . . ?
O2 C8 O1 116.96(15) . 3_656 ?
O2 C8 C6 125.81(16) . . ?
O1 C8 C6 117.23(13) 3_656 . ?

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 -0.2(2) . . . . ?
C7 C1 C2 C3 -179.54(16) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C5 C6 C8 -179.39(15) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
C7 C1 C6 C5 179.59(15) . . . . ?
C2 C1 C6 C8 179.54(15) . . . . ?
C7 C1 C6 C8 -1.1(2) . . . . ?
C8 O1 C7 C7 -0.2(3) 3_656 . . 3_656 ?
C8 O1 C7 C1 178.63(14) 3_656 . . . ?
C2 C1 C7 C7 178.58(19) . . . 3_656 ?
C6 C1 C7 C7 -0.8(3) . . . 3_656 ?
C2 C1 C7 O1 -0.2(2) . . . . ?
C6 C1 C7 O1 -179.55(14) . . . . ?
C5 C6 C8 O2 1.3(3) . . . . ?
C1 C6 C8 O2 -178.02(17) . . . . ?
C5 C6 C8 O1 -178.26(14) . . . 3_656 ?
C1 C6 C8 O1 2.4(2) . . . 3_656 ?

_refine_diff_density_max         0.328
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.053



####################################################################### 
# 
# 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_3b
_audit_block_doi                 10.5517/ccdc.csd.cc20cjnl
_database_code_depnum_ccdc_archive 'CCDC 1858129'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.orglett.8b03169 2018
loop_
_audit_author_name
_audit_author_address
'Yosuke Tani'
;Osaka University
Japan
;
_audit_update_record             
;
2018-07-31 deposited with the CCDC.	2021-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 O4'
_chemical_formula_weight         376.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   5.1379(7)
_cell_length_b                   5.6996(7)
_cell_length_c                   16.900(2)
_cell_angle_alpha                89.711(6)
_cell_angle_beta                 88.904(6)
_cell_angle_gamma                80.110(6)
_cell_volume                     487.45(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2700
_cell_measurement_theta_min      3.62
_cell_measurement_theta_max      27.475

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5251
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'Rigaku VariMax RAPID II'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4426
_diffrn_reflns_av_unetI/netI     0.1574
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.618
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             2179
_reflns_number_gt                984
_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       'Rigaku RAPID AUTO'
_computing_cell_refinement       'Rigaku RAPID AUTO'
_computing_data_reduction        'Rigaku RAPID AUTO'
_computing_structure_solution    Yadokari-SG
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_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)+(0.0660P)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         2179
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1250
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1284
_refine_ls_wR_factor_gt          0.1157
_refine_ls_goodness_of_fit_ref   0.820
_refine_ls_restrained_S_all      0.820
_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
C1 C 0.7908(4) 0.5546(3) 0.63610(11) 0.0264(5) Uani 1 1 d . . . . .
C2 C 0.6433(4) 0.5474(3) 0.70571(12) 0.0309(5) Uani 1 1 d . . . . .
H1 H 0.6632 0.6532 0.7476 0.037 Uiso 1 1 calc R U . . .
C3 C 0.4678(4) 0.3890(3) 0.71524(11) 0.0294(5) Uani 1 1 d . . . . .
C4 C 0.4448(4) 0.2350(4) 0.65289(12) 0.0326(5) Uani 1 1 d . . . . .
H2 H 0.3277 0.1237 0.6588 0.039 Uiso 1 1 calc R U . . .
C5 C 0.5868(4) 0.2393(3) 0.58298(11) 0.0292(5) Uani 1 1 d . . . . .
H3 H 0.5652 0.1335 0.5413 0.035 Uiso 1 1 calc R U . . .
C6 C 0.7628(4) 0.3998(3) 0.57351(11) 0.0276(5) Uani 1 1 d . . . . .
C7 C 0.9191(4) 0.4199(3) 0.50349(11) 0.0274(5) Uani 1 1 d . . . . .
O1 O 0.8934(3) 0.2657(2) 0.44218(7) 0.0293(4) Uani 1 1 d . . . . .
C8 C 1.0266(4) 0.2754(4) 0.37100(12) 0.0283(5) Uani 1 1 d . . . . .
O2 O 0.9833(3) 0.1396(2) 0.31987(8) 0.0342(4) Uani 1 1 d . . . . .
C9 C 0.3053(4) 0.3890(4) 0.79056(11) 0.0369(6) Uani 1 1 d . . . . .
H4 H 0.1782 0.2785 0.7839 0.044 Uiso 1 1 calc R U . . .
H5 H 0.2017 0.5506 0.7986 0.044 Uiso 1 1 calc R U . . .
C10 C 0.4639(5) 0.3174(4) 0.86467(12) 0.0434(6) Uani 1 1 d . . . . .
H6 H 0.5955 0.4267 0.8697 0.052 Uiso 1 1 calc R U . . .
C11 C 0.6152(6) 0.0646(4) 0.85983(14) 0.0561(8) Uani 1 1 d . . . . .
H7 H 0.7187 0.0278 0.9078 0.084 Uiso 1 1 calc R U . . .
H8 H 0.7342 0.0493 0.8134 0.084 Uiso 1 1 calc R U . . .
H9 H 0.4905 -0.0465 0.8552 0.084 Uiso 1 1 calc R U . . .
C12 C 0.2815(6) 0.3517(5) 0.93760(13) 0.0581(8) Uani 1 1 d . . . . .
H10 H 0.1927 0.5181 0.9404 0.087 Uiso 1 1 calc R U . . .
H11 H 0.3858 0.3116 0.9853 0.087 Uiso 1 1 calc R U . . .
H12 H 0.1491 0.2476 0.9339 0.087 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
C1 C2 1.391(3) . ?
C1 C6 1.406(3) . ?
C1 C8 1.463(3) 2_766 ?
C2 C3 1.388(3) . ?
C2 H1 0.9500 . ?
C3 C4 1.395(3) . ?
C3 C9 1.509(3) . ?
C4 C5 1.379(3) . ?
C4 H2 0.9500 . ?
C5 C6 1.399(3) . ?
C5 H3 0.9500 . ?
C6 C7 1.433(3) . ?
C7 C7 1.340(4) 2_766 ?
C7 O1 1.385(2) . ?
O1 C8 1.378(2) . ?
C8 O2 1.212(2) . ?
C8 C1 1.463(3) 2_766 ?
C9 C10 1.523(3) . ?
C9 H4 0.9900 . ?
C9 H5 0.9900 . ?
C10 C11 1.517(3) . ?
C10 C12 1.527(3) . ?
C10 H6 1.0000 . ?
C11 H7 0.9800 . ?
C11 H8 0.9800 . ?
C11 H9 0.9800 . ?
C12 H10 0.9800 . ?
C12 H11 0.9800 . ?
C12 H12 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
C2 C1 C6 119.96(18) . . ?
C2 C1 C8 119.3(2) . 2_766 ?
C6 C1 C8 120.76(18) . 2_766 ?
C3 C2 C1 121.4(2) . . ?
C3 C2 H1 119.3 . . ?
C1 C2 H1 119.3 . . ?
C2 C3 C4 117.91(19) . . ?
C2 C3 C9 120.3(2) . . ?
C4 C3 C9 121.76(18) . . ?
C5 C4 C3 122.00(19) . . ?
C5 C4 H2 119.0 . . ?
C3 C4 H2 119.0 . . ?
C4 C5 C6 119.9(2) . . ?
C4 C5 H3 120.0 . . ?
C6 C5 H3 120.0 . . ?
C5 C6 C1 118.86(18) . . ?
C5 C6 C7 124.51(19) . . ?
C1 C6 C7 116.62(18) . . ?
C7 C7 O1 121.1(2) 2_766 . ?
C7 C7 C6 122.4(3) 2_766 . ?
O1 C7 C6 116.56(17) . . ?
C8 O1 C7 121.49(16) . . ?
O2 C8 O1 116.67(18) . . ?
O2 C8 C1 125.73(19) . 2_766 ?
O1 C8 C1 117.6(2) . 2_766 ?
C3 C9 C10 114.96(18) . . ?
C3 C9 H4 108.5 . . ?
C10 C9 H4 108.5 . . ?
C3 C9 H5 108.5 . . ?
C10 C9 H5 108.5 . . ?
H4 C9 H5 107.5 . . ?
C11 C10 C9 112.2(2) . . ?
C11 C10 C12 111.32(17) . . ?
C9 C10 C12 109.8(2) . . ?
C11 C10 H6 107.8 . . ?
C9 C10 H6 107.8 . . ?
C12 C10 H6 107.8 . . ?
C10 C11 H7 109.5 . . ?
C10 C11 H8 109.5 . . ?
H7 C11 H8 109.5 . . ?
C10 C11 H9 109.5 . . ?
H7 C11 H9 109.5 . . ?
H8 C11 H9 109.5 . . ?
C10 C12 H10 109.5 . . ?
C10 C12 H11 109.5 . . ?
H10 C12 H11 109.5 . . ?
C10 C12 H12 109.5 . . ?
H10 C12 H12 109.5 . . ?
H11 C12 H12 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 0.2(3) . . . . ?
C8 C1 C2 C3 -179.92(18) 2_766 . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C1 C2 C3 C9 -178.50(18) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C9 C3 C4 C5 177.96(19) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C5 C6 C7 -179.79(19) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C8 C1 C6 C5 179.70(17) 2_766 . . . ?
C2 C1 C6 C7 179.30(18) . . . . ?
C8 C1 C6 C7 -0.5(2) 2_766 . . . ?
C5 C6 C7 C7 178.5(2) . . . 2_766 ?
C1 C6 C7 C7 -1.2(3) . . . 2_766 ?
C5 C6 C7 O1 -0.9(3) . . . . ?
C1 C6 C7 O1 179.36(16) . . . . ?
C7 C7 O1 C8 -1.9(3) 2_766 . . . ?
C6 C7 O1 C8 177.48(17) . . . . ?
C7 O1 C8 O2 -177.15(16) . . . . ?
C7 O1 C8 C1 3.6(2) . . . 2_766 ?
C2 C3 C9 C10 -64.8(3) . . . . ?
C4 C3 C9 C10 116.2(2) . . . . ?
C3 C9 C10 C11 -62.1(3) . . . . ?
C3 C9 C10 C12 173.54(19) . . . . ?

_refine_diff_density_max         0.296
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.050



####################################################################### 
# 
# 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_3c
_audit_block_doi                 10.5517/ccdc.csd.cc20dsdm
_database_code_depnum_ccdc_archive 'CCDC 1859330'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.orglett.8b03169 2018
loop_
_audit_author_name
_audit_author_address
'Yosuke Tani'
;Osaka University
Japan
;
_audit_update_record             
;
2018-07-31 deposited with the CCDC.	2021-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H6 F2 O4'
_chemical_formula_weight         300.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.1445(7)
_cell_length_b                   6.0709(7)
_cell_length_c                   11.9097(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.416(7)
_cell_angle_gamma                90
_cell_volume                     583.94(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2704
_cell_measurement_theta_min      3.45
_cell_measurement_theta_max      27.47

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.144
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6860
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating anode X-ray tube'
_diffrn_measurement_device_type  'Rigaku VariMax RAPID II'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5349
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.234
_diffrn_reflns_theta_max         27.469
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1332
_reflns_number_gt                864
_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       'Rigaku RAPID AUTO'
_computing_cell_refinement       'Rigaku RAPID AUTO'
_computing_data_reduction        'Rigaku RAPID AUTO'
_computing_structure_solution    Yadokari-SG
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_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)+(0.0594P)²+0.1875P] 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         1332
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1250
_refine_ls_wR_factor_gt          0.1083
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
C1 C 0.2094(3) 0.0425(4) 0.08389(17) 0.0203(5) Uani 1 1 d . . . . .
C2 C 0.2975(3) 0.1958(4) 0.15631(17) 0.0232(5) Uani 1 1 d . . . . .
H1 H 0.2478 0.3293 0.1762 0.028 Uiso 1 1 calc R U . . .
C3 C 0.4590(3) 0.1453(4) 0.19745(18) 0.0239(5) Uani 1 1 d . . . . .
C4 C 0.5376(3) -0.0481(4) 0.17257(18) 0.0264(5) Uani 1 1 d . . . . .
H2 H 0.6487 -0.0768 0.2040 0.032 Uiso 1 1 calc R U . . .
C5 C 0.4501(3) -0.1973(4) 0.10122(18) 0.0239(5) Uani 1 1 d . . . . .
H3 H 0.5015 -0.3305 0.0825 0.029 Uiso 1 1 calc R U . . .
C6 C 0.2861(3) -0.1542(4) 0.05597(17) 0.0219(5) Uani 1 1 d . . . . .
C7 C 0.1985(3) -0.3118(4) -0.02330(19) 0.0239(5) Uani 1 1 d . . . . .
O1 O 0.03527(18) -0.2647(2) -0.06424(12) 0.0236(4) Uani 1 1 d . . . . .
C8 C -0.0405(3) -0.0748(3) -0.03450(17) 0.0205(5) Uani 1 1 d . . . . .
O2 O 0.2549(2) -0.4793(3) -0.05664(13) 0.0307(4) Uani 1 1 d . . . . .
F1 F 0.54515(17) 0.2952(2) 0.26558(11) 0.0335(4) 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 C2 1.402(3) . ?
C1 C6 1.408(3) . ?
C1 C8 1.437(3) 3 ?
C2 C3 1.377(3) . ?
C2 H1 0.9500 . ?
C3 F1 1.353(3) . ?
C3 C4 1.387(3) . ?
C4 C5 1.376(3) . ?
C4 H2 0.9500 . ?
C5 C6 1.399(3) . ?
C5 H3 0.9500 . ?
C6 C7 1.463(3) . ?
C7 O2 1.204(3) . ?
C7 O1 1.386(3) . ?
O1 C8 1.376(2) . ?
C8 C8 1.340(4) 3 ?
C8 C1 1.437(3) 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
C2 C1 C6 120.04(19) . . ?
C2 C1 C8 123.3(2) . 3 ?
C6 C1 C8 116.71(19) . 3 ?
C3 C2 C1 117.5(2) . . ?
C3 C2 H1 121.3 . . ?
C1 C2 H1 121.3 . . ?
F1 C3 C2 117.5(2) . . ?
F1 C3 C4 118.66(19) . . ?
C2 C3 C4 123.9(2) . . ?
C5 C4 C3 118.2(2) . . ?
C5 C4 H2 120.9 . . ?
C3 C4 H2 120.9 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H3 119.8 . . ?
C6 C5 H3 119.8 . . ?
C5 C6 C1 119.9(2) . . ?
C5 C6 C7 119.2(2) . . ?
C1 C6 C7 120.84(19) . . ?
O2 C7 O1 116.6(2) . . ?
O2 C7 C6 126.2(2) . . ?
O1 C7 C6 117.25(19) . . ?
C8 O1 C7 121.63(17) . . ?
C8 C8 O1 121.6(2) 3 . ?
C8 C8 C1 121.9(2) 3 3 ?
O1 C8 C1 116.50(18) . 3 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_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 0.1(3) . . . . ?
C8 C1 C2 C3 -179.7(2) 3 . . . ?
C1 C2 C3 F1 178.74(19) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
F1 C3 C4 C5 -178.59(19) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C4 C5 C6 C7 177.5(2) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C8 C1 C6 C5 -179.8(2) 3 . . . ?
C2 C1 C6 C7 -177.3(2) . . . . ?
C8 C1 C6 C7 2.5(3) 3 . . . ?
C5 C6 C7 O2 -1.3(4) . . . . ?
C1 C6 C7 O2 176.5(2) . . . . ?
C5 C6 C7 O1 178.73(18) . . . . ?
C1 C6 C7 O1 -3.5(3) . . . . ?
O2 C7 O1 C8 -178.1(2) . . . . ?
C6 C7 O1 C8 1.9(3) . . . . ?
C7 O1 C8 C8 0.7(4) . . . 3 ?
C7 O1 C8 C1 178.99(19) . . . 3 ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.059



####################################################################### 
# 
# 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_3f
_audit_block_doi                 10.5517/ccdc.csd.cc20dsfn
_database_code_depnum_ccdc_archive 'CCDC 1859331'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.orglett.8b03169 2018
loop_
_audit_author_name
_audit_author_address
'Yosuke Tani'
;Osaka University
Japan
;
_audit_update_record             
;
2018-07-31 deposited with the CCDC.	2021-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H26 O4 S Si'
_chemical_formula_weight         426.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   9.4775(3)
_cell_length_b                   15.1136(4)
_cell_length_c                   16.9587(4)
_cell_angle_alpha                98.967(7)
_cell_angle_beta                 103.925(7)
_cell_angle_gamma                107.087(7)
_cell_volume                     2185.45(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    17013
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      27.46

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.229
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8812
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating anode X-ray tube'
_diffrn_measurement_device_type  'Rigaku VariMax RAPID II'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21594
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.992
_diffrn_reflns_theta_max         27.460
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             9945
_reflns_number_gt                8173
_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       'Rigaku RAPID AUTO'
_computing_cell_refinement       'Rigaku RAPID AUTO'
_computing_data_reduction        'Rigaku RAPID AUTO'
_computing_structure_solution    Yadokari-SG
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_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)+(0.0482P)²+0.7393P] 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         9945
_refine_ls_number_parameters     535
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0962
_refine_ls_wR_factor_gt          0.0904
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
O1 O -0.01506(11) 0.40104(7) 0.84188(6) 0.0198(2) Uani 1 1 d . . . . .
C1 C -0.10781(16) 0.35161(10) 0.88355(9) 0.0201(3) Uani 1 1 d . . . . .
O2 O -0.23733(12) 0.30166(8) 0.84243(7) 0.0291(2) Uani 1 1 d . . . . .
C2 C -0.03846(15) 0.36296(10) 0.97369(8) 0.0182(3) Uani 1 1 d . . . . .
C3 C -0.12913(16) 0.31128(10) 1.01624(9) 0.0208(3) Uani 1 1 d . . . . .
H1 H -0.2334 0.2716 0.9875 0.025 Uiso 1 1 calc R U . . .
C4 C -0.06670(18) 0.31818(11) 1.10016(9) 0.0239(3) Uani 1 1 d . . . . .
H2 H -0.1278 0.2829 1.1293 0.029 Uiso 1 1 calc R U . . .
C5 C 0.08638(18) 0.37707(11) 1.14249(9) 0.0257(3) Uani 1 1 d . . . . .
H3 H 0.1283 0.3815 1.2004 0.031 Uiso 1 1 calc R U . . .
C6 C 0.17786(17) 0.42905(11) 1.10141(9) 0.0226(3) Uani 1 1 d . . . . .
H4 H 0.2817 0.4689 1.1309 0.027 Uiso 1 1 calc R U . . .
C7 C 0.11593(15) 0.42234(10) 1.01578(8) 0.0178(3) Uani 1 1 d . . . . .
C8 C 0.19949(15) 0.47377(10) 0.96722(8) 0.0170(3) Uani 1 1 d . . . . .
O3 O 0.34643(11) 0.53714(7) 1.00847(6) 0.0189(2) Uani 1 1 d . . . . .
C9 C 0.43609(15) 0.59478(10) 0.96900(8) 0.0183(3) Uani 1 1 d . . . . .
O4 O 0.56349(11) 0.64744(8) 1.01166(6) 0.0258(2) Uani 1 1 d . . . . .
C10 C 0.36324(15) 0.58421(10) 0.88034(8) 0.0169(3) Uani 1 1 d . . . . .
C11 C 0.42445(16) 0.63793(10) 0.82690(8) 0.0186(3) Uani 1 1 d . . . . .
H5 H 0.5246 0.6855 0.8447 0.022 Uiso 1 1 calc R U . . .
C12 C 0.32496(16) 0.61445(10) 0.74704(8) 0.0190(3) Uani 1 1 d . . . . .
S1 S 0.15274(4) 0.52430(2) 0.73790(2) 0.01886(8) Uani 1 1 d . . . . .
C13 C 0.21556(15) 0.51926(10) 0.83991(8) 0.0168(3) Uani 1 1 d . . . . .
C14 C 0.13347(15) 0.46260(10) 0.88457(8) 0.0170(3) Uani 1 1 d . . . . .
Si1 Si 0.34303(4) 0.67559(3) 0.65922(2) 0.01770(9) Uani 1 1 d . . . . .
C15 C 0.27646(17) 0.78088(11) 0.67977(9) 0.0240(3) Uani 1 1 d . . . . .
H6 H 0.2839 0.8132 0.6330 0.029 Uiso 1 1 calc R U . . .
C16 C 0.55411(17) 0.72117(12) 0.66668(9) 0.0261(3) Uani 1 1 d . . . . .
H7 H 0.6085 0.7582 0.7261 0.031 Uiso 1 1 calc R U . . .
C17 C 0.20645(17) 0.58854(11) 0.55789(8) 0.0242(3) Uani 1 1 d . . . . .
H8 H 0.1041 0.5632 0.5680 0.029 Uiso 1 1 calc R U . . .
C18 C 0.3832(2) 0.85443(12) 0.76155(10) 0.0353(4) Uani 1 1 d . . . . .
H9 H 0.3521 0.9109 0.7673 0.053 Uiso 1 1 calc R U . . .
H10 H 0.4905 0.8730 0.7602 0.053 Uiso 1 1 calc R U . . .
H11 H 0.3749 0.8262 0.8092 0.053 Uiso 1 1 calc R U . . .
C19 C 0.10689(18) 0.75096(12) 0.67951(10) 0.0296(3) Uani 1 1 d . . . . .
H12 H 0.0943 0.7166 0.7233 0.044 Uiso 1 1 calc R U . . .
H13 H 0.0399 0.7092 0.6248 0.044 Uiso 1 1 calc R U . . .
H14 H 0.0782 0.8079 0.6903 0.044 Uiso 1 1 calc R U . . .
C20 C 0.6277(2) 0.64533(16) 0.65301(14) 0.0494(5) Uani 1 1 d . . . . .
H15 H 0.5909 0.6124 0.5935 0.074 Uiso 1 1 calc R U . . .
H16 H 0.5989 0.5991 0.6861 0.074 Uiso 1 1 calc R U . . .
H17 H 0.7406 0.6757 0.6707 0.074 Uiso 1 1 calc R U . . .
C21 C 0.5930(2) 0.79340(16) 0.61387(12) 0.0485(5) Uani 1 1 d . . . . .
H18 H 0.7057 0.8234 0.6287 0.073 Uiso 1 1 calc R U . . .
H19 H 0.5470 0.8425 0.6249 0.073 Uiso 1 1 calc R U . . .
H20 H 0.5510 0.7604 0.5543 0.073 Uiso 1 1 calc R U . . .
C22 C 0.1791(2) 0.63808(14) 0.48585(10) 0.0430(5) Uani 1 1 d . . . . .
H21 H 0.2767 0.6647 0.4736 0.065 Uiso 1 1 calc R U . . .
H22 H 0.1410 0.6896 0.5022 0.065 Uiso 1 1 calc R U . . .
H23 H 0.1023 0.5915 0.4358 0.065 Uiso 1 1 calc R U . . .
C23 C 0.2520(2) 0.50171(14) 0.53221(12) 0.0493(5) Uani 1 1 d . . . . .
H24 H 0.1672 0.4546 0.4856 0.074 Uiso 1 1 calc R U . . .
H25 H 0.2724 0.4731 0.5799 0.074 Uiso 1 1 calc R U . . .
H26 H 0.3454 0.5218 0.5147 0.074 Uiso 1 1 calc R U . . .
O5 O -0.01772(11) -0.09732(7) 0.85585(6) 0.0196(2) Uani 1 1 d . . . . .
C24 C -0.10495(16) -0.14504(10) 0.90068(8) 0.0204(3) Uani 1 1 d . . . . .
O6 O -0.23804(12) -0.19107(9) 0.86406(7) 0.0336(3) Uani 1 1 d . . . . .
C25 C -0.02629(15) -0.13567(9) 0.98936(8) 0.0166(3) Uani 1 1 d . . . . .
C26 C -0.11057(16) -0.18747(10) 1.03450(8) 0.0189(3) Uani 1 1 d . . . . .
H27 H -0.2157 -0.2272 1.0082 0.023 Uiso 1 1 calc R U . . .
C27 C -0.03974(16) -0.18049(10) 1.11772(8) 0.0201(3) Uani 1 1 d . . . . .
H28 H -0.0963 -0.2156 1.1488 0.024 Uiso 1 1 calc R U . . .
C28 C 0.11490(17) -0.12192(10) 1.15627(8) 0.0220(3) Uani 1 1 d . . . . .
H29 H 0.1623 -0.1175 1.2136 0.026 Uiso 1 1 calc R U . . .
C29 C 0.20009(16) -0.07031(10) 1.11230(8) 0.0194(3) Uani 1 1 d . . . . .
H30 H 0.3051 -0.0308 1.1392 0.023 Uiso 1 1 calc R U . . .
C30 C 0.12975(15) -0.07687(9) 1.02757(8) 0.0161(3) Uani 1 1 d . . . . .
C31 C 0.20621(15) -0.02543(9) 0.97638(8) 0.0160(3) Uani 1 1 d . . . . .
O7 O 0.35426(10) 0.03785(7) 1.01441(5) 0.0185(2) Uani 1 1 d . . . . .
C32 C 0.43534(15) 0.09749(10) 0.97315(8) 0.0183(3) Uani 1 1 d . . . . .
O8 O 0.56385(11) 0.15105(8) 1.01299(6) 0.0256(2) Uani 1 1 d . . . . .
C33 C 0.35410(15) 0.08755(10) 0.88581(8) 0.0170(3) Uani 1 1 d . . . . .
C34 C 0.40653(16) 0.14308(10) 0.83129(8) 0.0185(3) Uani 1 1 d . . . . .
H31 H 0.5048 0.1923 0.8473 0.022 Uiso 1 1 calc R U . . .
C35 C 0.30065(15) 0.11847(10) 0.75299(8) 0.0181(3) Uani 1 1 d . . . . .
S2 S 0.13499(4) 0.02506(2) 0.74646(2) 0.01735(8) Uani 1 1 d . . . . .
C36 C 0.20739(15) 0.02061(10) 0.84804(8) 0.0160(3) Uani 1 1 d . . . . .
C37 C 0.13235(15) -0.03671(9) 0.89481(8) 0.0162(3) Uani 1 1 d . . . . .
Si2 Si 0.31829(4) 0.17136(3) 0.66061(2) 0.01726(9) Uani 1 1 d . . . . .
C38 C 0.44700(17) 0.29989(11) 0.70579(9) 0.0250(3) Uani 1 1 d . . . . .
H32 H 0.5418 0.2978 0.7459 0.030 Uiso 1 1 calc R U . . .
C39 C 0.41596(16) 0.10530(11) 0.60038(8) 0.0220(3) Uani 1 1 d . . . . .
H33 H 0.4340 0.1367 0.5542 0.026 Uiso 1 1 calc R U . . .
C40 C 0.11412(16) 0.14825(11) 0.59286(8) 0.0233(3) Uani 1 1 d . . . . .
H34 H 0.0587 0.0779 0.5803 0.028 Uiso 1 1 calc R U . . .
C41 C 0.5051(3) 0.34875(14) 0.64199(13) 0.0520(5) Uani 1 1 d . . . . .
H35 H 0.4179 0.3552 0.6014 0.078 Uiso 1 1 calc R U . . .
H36 H 0.5529 0.3104 0.6127 0.078 Uiso 1 1 calc R U . . .
H37 H 0.5819 0.4122 0.6708 0.078 Uiso 1 1 calc R U . . .
C42 C 0.3837(2) 0.36031(12) 0.75841(12) 0.0398(4) Uani 1 1 d . . . . .
H38 H 0.4646 0.4224 0.7872 0.060 Uiso 1 1 calc R U . . .
H39 H 0.3509 0.3276 0.7999 0.060 Uiso 1 1 calc R U . . .
H40 H 0.2948 0.3699 0.7220 0.060 Uiso 1 1 calc R U . . .
C43 C 0.57423(18) 0.11158(13) 0.65622(10) 0.0325(4) Uani 1 1 d . . . . .
H41 H 0.5600 0.0817 0.7024 0.049 Uiso 1 1 calc R U . . .
H42 H 0.6405 0.1787 0.6790 0.049 Uiso 1 1 calc R U . . .
H43 H 0.6231 0.0783 0.6229 0.049 Uiso 1 1 calc R U . . .
C44 C 0.3153(2) 0.00004(12) 0.56035(10) 0.0325(4) Uani 1 1 d . . . . .
H44 H 0.3720 -0.0317 0.5316 0.049 Uiso 1 1 calc R U . . .
H45 H 0.2192 -0.0038 0.5198 0.049 Uiso 1 1 calc R U . . .
H46 H 0.2905 -0.0315 0.6041 0.049 Uiso 1 1 calc R U . . .
C45 C 0.11015(19) 0.17242(15) 0.50778(10) 0.0402(4) Uani 1 1 d . . . . .
H47 H 0.0023 0.1559 0.4738 0.060 Uiso 1 1 calc R U . . .
H48 H 0.1605 0.1359 0.4786 0.060 Uiso 1 1 calc R U . . .
H49 H 0.1651 0.2408 0.5167 0.060 Uiso 1 1 calc R U . . .
C46 C 0.01923(18) 0.19555(13) 0.63455(10) 0.0340(4) Uani 1 1 d . . . . .
H50 H 0.0626 0.2649 0.6429 0.051 Uiso 1 1 calc R U . . .
H51 H 0.0229 0.1801 0.6889 0.051 Uiso 1 1 calc R U . . .
H52 H -0.0885 0.1719 0.5986 0.051 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
O1 C14 1.3788(15) . ?
O1 C1 1.3812(17) . ?
C1 O2 1.2010(17) . ?
C1 C2 1.4720(19) . ?
C2 C3 1.3960(19) . ?
C2 C7 1.4078(18) . ?
C3 C4 1.378(2) . ?
C3 H1 0.9500 . ?
C4 C5 1.398(2) . ?
C4 H2 0.9500 . ?
C5 C6 1.384(2) . ?
C5 H3 0.9500 . ?
C6 C7 1.4046(19) . ?
C6 H4 0.9500 . ?
C7 C8 1.4356(19) . ?
C8 C14 1.3515(18) . ?
C8 O3 1.3728(15) . ?
O3 C9 1.3963(16) . ?
C9 O4 1.2043(16) . ?
C9 C10 1.4572(18) . ?
C10 C13 1.3833(18) . ?
C10 C11 1.4222(18) . ?
C11 C12 1.3741(18) . ?
C11 H5 0.9500 . ?
C12 S1 1.7464(14) . ?
C12 Si1 1.8868(14) . ?
S1 C13 1.7101(13) . ?
C13 C14 1.4166(19) . ?
Si1 C16 1.8798(15) . ?
Si1 C15 1.8906(15) . ?
Si1 C17 1.8929(14) . ?
C15 C19 1.535(2) . ?
C15 C18 1.538(2) . ?
C15 H6 1.0000 . ?
C16 C20 1.523(2) . ?
C16 C21 1.535(2) . ?
C16 H7 1.0000 . ?
C17 C23 1.531(2) . ?
C17 C22 1.539(2) . ?
C17 H8 1.0000 . ?
C18 H9 0.9800 . ?
C18 H10 0.9800 . ?
C18 H11 0.9800 . ?
C19 H12 0.9800 . ?
C19 H13 0.9800 . ?
C19 H14 0.9800 . ?
C20 H15 0.9800 . ?
C20 H16 0.9800 . ?
C20 H17 0.9800 . ?
C21 H18 0.9800 . ?
C21 H19 0.9800 . ?
C21 H20 0.9800 . ?
C22 H21 0.9800 . ?
C22 H22 0.9800 . ?
C22 H23 0.9800 . ?
C23 H24 0.9800 . ?
C23 H25 0.9800 . ?
C23 H26 0.9800 . ?
O5 C37 1.3755(15) . ?
O5 C24 1.3801(16) . ?
C24 O6 1.1972(17) . ?
C24 C25 1.4728(18) . ?
C25 C26 1.3966(19) . ?
C25 C30 1.4084(18) . ?
C26 C27 1.3819(19) . ?
C26 H27 0.9500 . ?
C27 C28 1.398(2) . ?
C27 H28 0.9500 . ?
C28 C29 1.3847(19) . ?
C28 H29 0.9500 . ?
C29 C30 1.4052(18) . ?
C29 H30 0.9500 . ?
C30 C31 1.4372(18) . ?
C31 C37 1.3501(18) . ?
C31 O7 1.3723(15) . ?
O7 C32 1.3932(16) . ?
C32 O8 1.2039(16) . ?
C32 C33 1.4570(18) . ?
C33 C36 1.3820(18) . ?
C33 C34 1.4228(18) . ?
C34 C35 1.3761(18) . ?
C34 H31 0.9500 . ?
C35 S2 1.7422(14) . ?
C35 Si2 1.8866(14) . ?
S2 C36 1.7140(13) . ?
C36 C37 1.4173(18) . ?
Si2 C38 1.8821(16) . ?
Si2 C39 1.8914(15) . ?
Si2 C40 1.8958(14) . ?
C38 C41 1.522(2) . ?
C38 C42 1.522(2) . ?
C38 H32 1.0000 . ?
C39 C43 1.536(2) . ?
C39 C44 1.537(2) . ?
C39 H33 1.0000 . ?
C40 C46 1.532(2) . ?
C40 C45 1.537(2) . ?
C40 H34 1.0000 . ?
C41 H35 0.9800 . ?
C41 H36 0.9800 . ?
C41 H37 0.9800 . ?
C42 H38 0.9800 . ?
C42 H39 0.9800 . ?
C42 H40 0.9800 . ?
C43 H41 0.9800 . ?
C43 H42 0.9800 . ?
C43 H43 0.9800 . ?
C44 H44 0.9800 . ?
C44 H45 0.9800 . ?
C44 H46 0.9800 . ?
C45 H47 0.9800 . ?
C45 H48 0.9800 . ?
C45 H49 0.9800 . ?
C46 H50 0.9800 . ?
C46 H51 0.9800 . ?
C46 H52 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 O1 C1 120.83(10) . . ?
O2 C1 O1 116.84(12) . . ?
O2 C1 C2 125.80(13) . . ?
O1 C1 C2 117.34(12) . . ?
C3 C2 C7 120.64(13) . . ?
C3 C2 C1 118.08(12) . . ?
C7 C2 C1 121.26(13) . . ?
C4 C3 C2 119.67(13) . . ?
C4 C3 H1 120.2 . . ?
C2 C3 H1 120.2 . . ?
C3 C4 C5 120.09(14) . . ?
C3 C4 H2 120.0 . . ?
C5 C4 H2 120.0 . . ?
C6 C5 C4 121.05(14) . . ?
C6 C5 H3 119.5 . . ?
C4 C5 H3 119.5 . . ?
C5 C6 C7 119.46(14) . . ?
C5 C6 H4 120.3 . . ?
C7 C6 H4 120.3 . . ?
C6 C7 C2 119.09(13) . . ?
C6 C7 C8 124.20(13) . . ?
C2 C7 C8 116.71(12) . . ?
C14 C8 O3 121.37(12) . . ?
C14 C8 C7 121.05(12) . . ?
O3 C8 C7 117.54(11) . . ?
C8 O3 C9 122.86(10) . . ?
O4 C9 O3 116.82(12) . . ?
O4 C9 C10 127.53(13) . . ?
O3 C9 C10 115.66(11) . . ?
C13 C10 C11 112.34(12) . . ?
C13 C10 C9 120.46(12) . . ?
C11 C10 C9 127.14(12) . . ?
C12 C11 C10 113.60(12) . . ?
C12 C11 H5 123.2 . . ?
C10 C11 H5 123.2 . . ?
C11 C12 S1 110.02(10) . . ?
C11 C12 Si1 129.01(11) . . ?
S1 C12 Si1 120.42(7) . . ?
C13 S1 C12 92.55(7) . . ?
C10 C13 C14 120.16(12) . . ?
C10 C13 S1 111.50(10) . . ?
C14 C13 S1 128.25(10) . . ?
C8 C14 O1 122.66(12) . . ?
C8 C14 C13 119.47(12) . . ?
O1 C14 C13 117.80(11) . . ?
C16 Si1 C12 107.50(6) . . ?
C16 Si1 C15 108.82(7) . . ?
C12 Si1 C15 106.50(6) . . ?
C16 Si1 C17 116.74(7) . . ?
C12 Si1 C17 107.75(7) . . ?
C15 Si1 C17 109.06(7) . . ?
C19 C15 C18 110.81(13) . . ?
C19 C15 Si1 112.70(11) . . ?
C18 C15 Si1 111.56(10) . . ?
C19 C15 H6 107.1 . . ?
C18 C15 H6 107.1 . . ?
Si1 C15 H6 107.1 . . ?
C20 C16 C21 110.96(15) . . ?
C20 C16 Si1 115.81(12) . . ?
C21 C16 Si1 113.57(12) . . ?
C20 C16 H7 105.1 . . ?
C21 C16 H7 105.1 . . ?
Si1 C16 H7 105.1 . . ?
C23 C17 C22 111.31(15) . . ?
C23 C17 Si1 114.16(11) . . ?
C22 C17 Si1 112.12(11) . . ?
C23 C17 H8 106.2 . . ?
C22 C17 H8 106.2 . . ?
Si1 C17 H8 106.2 . . ?
C15 C18 H9 109.5 . . ?
C15 C18 H10 109.5 . . ?
H9 C18 H10 109.5 . . ?
C15 C18 H11 109.5 . . ?
H9 C18 H11 109.5 . . ?
H10 C18 H11 109.5 . . ?
C15 C19 H12 109.5 . . ?
C15 C19 H13 109.5 . . ?
H12 C19 H13 109.5 . . ?
C15 C19 H14 109.5 . . ?
H12 C19 H14 109.5 . . ?
H13 C19 H14 109.5 . . ?
C16 C20 H15 109.5 . . ?
C16 C20 H16 109.5 . . ?
H15 C20 H16 109.5 . . ?
C16 C20 H17 109.5 . . ?
H15 C20 H17 109.5 . . ?
H16 C20 H17 109.5 . . ?
C16 C21 H18 109.5 . . ?
C16 C21 H19 109.5 . . ?
H18 C21 H19 109.5 . . ?
C16 C21 H20 109.5 . . ?
H18 C21 H20 109.5 . . ?
H19 C21 H20 109.5 . . ?
C17 C22 H21 109.5 . . ?
C17 C22 H22 109.5 . . ?
H21 C22 H22 109.5 . . ?
C17 C22 H23 109.5 . . ?
H21 C22 H23 109.5 . . ?
H22 C22 H23 109.5 . . ?
C17 C23 H24 109.5 . . ?
C17 C23 H25 109.5 . . ?
H24 C23 H25 109.5 . . ?
C17 C23 H26 109.5 . . ?
H24 C23 H26 109.5 . . ?
H25 C23 H26 109.5 . . ?
C37 O5 C24 120.85(10) . . ?
O6 C24 O5 117.22(12) . . ?
O6 C24 C25 125.47(13) . . ?
O5 C24 C25 117.30(12) . . ?
C26 C25 C30 120.79(12) . . ?
C26 C25 C24 118.07(12) . . ?
C30 C25 C24 121.14(12) . . ?
C27 C26 C25 119.42(13) . . ?
C27 C26 H27 120.3 . . ?
C25 C26 H27 120.3 . . ?
C26 C27 C28 120.17(13) . . ?
C26 C27 H28 119.9 . . ?
C28 C27 H28 119.9 . . ?
C29 C28 C27 121.09(13) . . ?
C29 C28 H29 119.5 . . ?
C27 C28 H29 119.5 . . ?
C28 C29 C30 119.39(13) . . ?
C28 C29 H30 120.3 . . ?
C30 C29 H30 120.3 . . ?
C29 C30 C25 119.14(12) . . ?
C29 C30 C31 124.11(12) . . ?
C25 C30 C31 116.74(12) . . ?
C37 C31 O7 121.62(12) . . ?
C37 C31 C30 120.91(12) . . ?
O7 C31 C30 117.42(11) . . ?
C31 O7 C32 122.68(10) . . ?
O8 C32 O7 116.98(12) . . ?
O8 C32 C33 127.23(13) . . ?
O7 C32 C33 115.79(11) . . ?
C36 C33 C34 112.49(12) . . ?
C36 C33 C32 120.37(12) . . ?
C34 C33 C32 127.10(12) . . ?
C35 C34 C33 113.29(12) . . ?
C35 C34 H31 123.4 . . ?
C33 C34 H31 123.4 . . ?
C34 C35 S2 110.33(10) . . ?
C34 C35 Si2 128.57(11) . . ?
S2 C35 Si2 121.10(7) . . ?
C36 S2 C35 92.45(6) . . ?
C33 C36 C37 120.24(12) . . ?
C33 C36 S2 111.44(10) . . ?
C37 C36 S2 128.19(10) . . ?
C31 C37 O5 122.81(12) . . ?
C31 C37 C36 119.22(12) . . ?
O5 C37 C36 117.83(11) . . ?
C38 Si2 C35 106.06(6) . . ?
C38 Si2 C39 109.80(7) . . ?
C35 Si2 C39 107.32(6) . . ?
C38 Si2 C40 116.75(7) . . ?
C35 Si2 C40 106.96(6) . . ?
C39 Si2 C40 109.48(6) . . ?
C41 C38 C42 111.86(15) . . ?
C41 C38 Si2 113.76(11) . . ?
C42 C38 Si2 115.00(11) . . ?
C41 C38 H32 105.0 . . ?
C42 C38 H32 105.0 . . ?
Si2 C38 H32 105.0 . . ?
C43 C39 C44 109.54(13) . . ?
C43 C39 Si2 111.41(10) . . ?
C44 C39 Si2 112.43(10) . . ?
C43 C39 H33 107.8 . . ?
C44 C39 H33 107.8 . . ?
Si2 C39 H33 107.8 . . ?
C46 C40 C45 110.02(13) . . ?
C46 C40 Si2 115.27(10) . . ?
C45 C40 Si2 112.42(10) . . ?
C46 C40 H34 106.1 . . ?
C45 C40 H34 106.1 . . ?
Si2 C40 H34 106.1 . . ?
C38 C41 H35 109.5 . . ?
C38 C41 H36 109.5 . . ?
H35 C41 H36 109.5 . . ?
C38 C41 H37 109.5 . . ?
H35 C41 H37 109.5 . . ?
H36 C41 H37 109.5 . . ?
C38 C42 H38 109.5 . . ?
C38 C42 H39 109.5 . . ?
H38 C42 H39 109.5 . . ?
C38 C42 H40 109.5 . . ?
H38 C42 H40 109.5 . . ?
H39 C42 H40 109.5 . . ?
C39 C43 H41 109.5 . . ?
C39 C43 H42 109.5 . . ?
H41 C43 H42 109.5 . . ?
C39 C43 H43 109.5 . . ?
H41 C43 H43 109.5 . . ?
H42 C43 H43 109.5 . . ?
C39 C44 H44 109.5 . . ?
C39 C44 H45 109.5 . . ?
H44 C44 H45 109.5 . . ?
C39 C44 H46 109.5 . . ?
H44 C44 H46 109.5 . . ?
H45 C44 H46 109.5 . . ?
C40 C45 H47 109.5 . . ?
C40 C45 H48 109.5 . . ?
H47 C45 H48 109.5 . . ?
C40 C45 H49 109.5 . . ?
H47 C45 H49 109.5 . . ?
H48 C45 H49 109.5 . . ?
C40 C46 H50 109.5 . . ?
C40 C46 H51 109.5 . . ?
H50 C46 H51 109.5 . . ?
C40 C46 H52 109.5 . . ?
H50 C46 H52 109.5 . . ?
H51 C46 H52 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
C14 O1 C1 O2 177.75(13) . . . . ?
C14 O1 C1 C2 -3.63(18) . . . . ?
O2 C1 C2 C3 0.4(2) . . . . ?
O1 C1 C2 C3 -178.12(12) . . . . ?
O2 C1 C2 C7 178.90(14) . . . . ?
O1 C1 C2 C7 0.4(2) . . . . ?
C7 C2 C3 C4 -0.3(2) . . . . ?
C1 C2 C3 C4 178.28(13) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C4 C5 C6 C7 -0.1(2) . . . . ?
C5 C6 C7 C2 0.2(2) . . . . ?
C5 C6 C7 C8 179.24(14) . . . . ?
C3 C2 C7 C6 0.0(2) . . . . ?
C1 C2 C7 C6 -178.53(13) . . . . ?
C3 C2 C7 C8 -179.12(12) . . . . ?
C1 C2 C7 C8 2.38(19) . . . . ?
C6 C7 C8 C14 178.82(14) . . . . ?
C2 C7 C8 C14 -2.1(2) . . . . ?
C6 C7 C8 O3 -3.5(2) . . . . ?
C2 C7 C8 O3 175.50(11) . . . . ?
C14 C8 O3 C9 1.0(2) . . . . ?
C7 C8 O3 C9 -176.66(12) . . . . ?
C8 O3 C9 O4 -179.83(12) . . . . ?
C8 O3 C9 C10 0.47(18) . . . . ?
O4 C9 C10 C13 179.29(14) . . . . ?
O3 C9 C10 C13 -1.05(19) . . . . ?
O4 C9 C10 C11 -3.8(2) . . . . ?
O3 C9 C10 C11 175.82(12) . . . . ?
C13 C10 C11 C12 0.11(17) . . . . ?
C9 C10 C11 C12 -176.97(13) . . . . ?
C10 C11 C12 S1 -0.03(15) . . . . ?
C10 C11 C12 Si1 171.36(10) . . . . ?
C11 C12 S1 C13 -0.04(11) . . . . ?
Si1 C12 S1 C13 -172.28(9) . . . . ?
C11 C10 C13 C14 -177.04(12) . . . . ?
C9 C10 C13 C14 0.3(2) . . . . ?
C11 C10 C13 S1 -0.13(15) . . . . ?
C9 C10 C13 S1 177.17(10) . . . . ?
C12 S1 C13 C10 0.10(11) . . . . ?
C12 S1 C13 C14 176.69(13) . . . . ?
O3 C8 C14 O1 -178.58(11) . . . . ?
C7 C8 C14 O1 -1.0(2) . . . . ?
O3 C8 C14 C13 -1.8(2) . . . . ?
C7 C8 C14 C13 175.75(12) . . . . ?
C1 O1 C14 C8 4.1(2) . . . . ?
C1 O1 C14 C13 -172.75(12) . . . . ?
C10 C13 C14 C8 1.2(2) . . . . ?
S1 C13 C14 C8 -175.15(11) . . . . ?
C10 C13 C14 O1 178.11(12) . . . . ?
S1 C13 C14 O1 1.77(19) . . . . ?
C11 C12 Si1 C16 35.49(15) . . . . ?
S1 C12 Si1 C16 -153.90(9) . . . . ?
C11 C12 Si1 C15 -81.01(14) . . . . ?
S1 C12 Si1 C15 89.61(9) . . . . ?
C11 C12 Si1 C17 162.09(13) . . . . ?
S1 C12 Si1 C17 -27.30(10) . . . . ?
C16 Si1 C15 C19 -177.04(10) . . . . ?
C12 Si1 C15 C19 -61.43(11) . . . . ?
C17 Si1 C15 C19 54.59(12) . . . . ?
C16 Si1 C15 C18 -51.62(13) . . . . ?
C12 Si1 C15 C18 63.99(13) . . . . ?
C17 Si1 C15 C18 -179.99(11) . . . . ?
C12 Si1 C16 C20 64.16(14) . . . . ?
C15 Si1 C16 C20 179.12(12) . . . . ?
C17 Si1 C16 C20 -56.95(14) . . . . ?
C12 Si1 C16 C21 -165.72(12) . . . . ?
C15 Si1 C16 C21 -50.75(14) . . . . ?
C17 Si1 C16 C21 73.17(15) . . . . ?
C16 Si1 C17 C23 53.74(15) . . . . ?
C12 Si1 C17 C23 -67.24(14) . . . . ?
C15 Si1 C17 C23 177.54(13) . . . . ?
C16 Si1 C17 C22 -74.03(14) . . . . ?
C12 Si1 C17 C22 164.99(12) . . . . ?
C15 Si1 C17 C22 49.77(13) . . . . ?
C37 O5 C24 O6 174.63(13) . . . . ?
C37 O5 C24 C25 -5.82(18) . . . . ?
O6 C24 C25 C26 2.8(2) . . . . ?
O5 C24 C25 C26 -176.69(12) . . . . ?
O6 C24 C25 C30 -177.69(15) . . . . ?
O5 C24 C25 C30 2.80(19) . . . . ?
C30 C25 C26 C27 0.2(2) . . . . ?
C24 C25 C26 C27 179.72(12) . . . . ?
C25 C26 C27 C28 0.1(2) . . . . ?
C26 C27 C28 C29 -0.2(2) . . . . ?
C27 C28 C29 C30 0.1(2) . . . . ?
C28 C29 C30 C25 0.2(2) . . . . ?
C28 C29 C30 C31 178.96(13) . . . . ?
C26 C25 C30 C29 -0.4(2) . . . . ?
C24 C25 C30 C29 -179.86(12) . . . . ?
C26 C25 C30 C31 -179.21(12) . . . . ?
C24 C25 C30 C31 1.31(19) . . . . ?
C29 C30 C31 C37 178.64(13) . . . . ?
C25 C30 C31 C37 -2.60(19) . . . . ?
C29 C30 C31 O7 -3.8(2) . . . . ?
C25 C30 C31 O7 174.99(11) . . . . ?
C37 C31 O7 C32 3.05(19) . . . . ?
C30 C31 O7 C32 -174.53(11) . . . . ?
C31 O7 C32 O8 179.08(12) . . . . ?
C31 O7 C32 C33 -1.08(18) . . . . ?
O8 C32 C33 C36 178.30(14) . . . . ?
O7 C32 C33 C36 -1.52(19) . . . . ?
O8 C32 C33 C34 -4.1(2) . . . . ?
O7 C32 C33 C34 176.10(12) . . . . ?
C36 C33 C34 C35 -0.02(17) . . . . ?
C32 C33 C34 C35 -177.80(13) . . . . ?
C33 C34 C35 S2 -0.42(15) . . . . ?
C33 C34 C35 Si2 -179.91(10) . . . . ?
C34 C35 S2 C36 0.58(11) . . . . ?
Si2 C35 S2 C36 -179.89(9) . . . . ?
C34 C33 C36 C37 -175.70(12) . . . . ?
C32 C33 C36 C37 2.2(2) . . . . ?
C34 C33 C36 S2 0.46(15) . . . . ?
C32 C33 C36 S2 178.40(10) . . . . ?
C35 S2 C36 C33 -0.59(11) . . . . ?
C35 S2 C36 C37 175.18(13) . . . . ?
O7 C31 C37 O5 -177.84(11) . . . . ?
C30 C31 C37 O5 -0.3(2) . . . . ?
O7 C31 C37 C36 -2.3(2) . . . . ?
C30 C31 C37 C36 175.22(12) . . . . ?
C24 O5 C37 C31 4.8(2) . . . . ?
C24 O5 C37 C36 -170.81(12) . . . . ?
C33 C36 C37 C31 -0.4(2) . . . . ?
S2 C36 C37 C31 -175.81(11) . . . . ?
C33 C36 C37 O5 175.42(12) . . . . ?
S2 C36 C37 O5 -0.02(19) . . . . ?
C34 C35 Si2 C38 -30.09(15) . . . . ?
S2 C35 Si2 C38 150.47(8) . . . . ?
C34 C35 Si2 C39 87.23(14) . . . . ?
S2 C35 Si2 C39 -92.21(9) . . . . ?
C34 C35 Si2 C40 -155.37(13) . . . . ?
S2 C35 Si2 C40 25.19(10) . . . . ?
C35 Si2 C38 C41 166.75(13) . . . . ?
C39 Si2 C38 C41 51.10(15) . . . . ?
C40 Si2 C38 C41 -74.23(15) . . . . ?
C35 Si2 C38 C42 -62.40(13) . . . . ?
C39 Si2 C38 C42 -178.05(12) . . . . ?
C40 Si2 C38 C42 56.62(14) . . . . ?
C38 Si2 C39 C43 57.68(13) . . . . ?
C35 Si2 C39 C43 -57.18(12) . . . . ?
C40 Si2 C39 C43 -172.92(11) . . . . ?
C38 Si2 C39 C44 -178.92(10) . . . . ?
C35 Si2 C39 C44 66.23(11) . . . . ?
C40 Si2 C39 C44 -49.52(12) . . . . ?
C38 Si2 C40 C46 -55.96(14) . . . . ?
C35 Si2 C40 C46 62.57(13) . . . . ?
C39 Si2 C40 C46 178.55(11) . . . . ?
C38 Si2 C40 C45 71.22(14) . . . . ?
C35 Si2 C40 C45 -170.25(12) . . . . ?
C39 Si2 C40 C45 -54.27(14) . . . . ?

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.048



####################################################################### 
# 
# 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_3e
_audit_block_doi                 10.5517/ccdc.csd.cc20dshq
_database_code_depnum_ccdc_archive 'CCDC 1859333'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.orglett.8b03169 2018
loop_
_audit_author_name
_audit_author_address
'Yosuke Tani'
;Osaka University
Japan
;
_audit_update_record             
;
2018-07-31 deposited with the CCDC.	2021-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H44 O4 S2 Si2'
_chemical_formula_weight         588.95

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      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                   15.0426(3)
_cell_length_b                   15.2812(3)
_cell_length_c                   14.9348(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.531(8)
_cell_angle_gamma                90
_cell_volume                     3273.60(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    22988
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.455

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.267
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8390
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'Rigaku VariMax RAPID II'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31401
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.021
_diffrn_reflns_theta_max         27.456
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7469
_reflns_number_gt                6089
_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       'Rigaku RAPID AUTO'
_computing_cell_refinement       'Rigaku RAPID AUTO'
_computing_data_reduction        'Rigaku RAPID AUTO'
_computing_structure_solution    Yadokari-SG
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_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)+(0.0442P)²+2.2983P] 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         7469
_refine_ls_number_parameters     355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1048
_refine_ls_wR_factor_gt          0.0994
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 0.09342(3) 0.49135(3) 0.34576(3) 0.02126(11) Uani 1 1 d . . . . .
C1 C 0.00184(13) 0.52081(12) 0.24797(13) 0.0211(4) Uani 1 1 d . . . . .
C2 C 0.01718(13) 0.48895(12) 0.16804(13) 0.0218(4) Uani 1 1 d . . . . .
H1 H -0.0249 0.4980 0.1070 0.026 Uiso 1 1 calc R U . . .
C3 C 0.10085(12) 0.44170(12) 0.18444(13) 0.0198(4) Uani 1 1 d . . . . .
C4 C 0.15099(12) 0.43793(11) 0.27855(12) 0.0174(3) Uani 1 1 d . . . . .
C5 C 0.23838(12) 0.39544(11) 0.30787(12) 0.0185(4) Uani 1 1 d . . . . .
C6 C 0.27208(12) 0.35950(11) 0.24194(12) 0.0179(4) Uani 1 1 d . . . . .
C7 C 0.36088(12) 0.31717(11) 0.27212(12) 0.0177(3) Uani 1 1 d . . . . .
C8 C 0.40945(12) 0.31409(12) 0.36610(13) 0.0192(4) Uani 1 1 d . . . . .
C9 C 0.49248(11) 0.26635(11) 0.38331(12) 0.0173(3) Uani 1 1 d . . . . .
H2 H 0.5346 0.2588 0.4446 0.021 Uiso 1 1 calc R U . . .
C10 C 0.50833(12) 0.23128(12) 0.30451(13) 0.0207(4) Uani 1 1 d . . . . .
S2 S 0.41717(3) 0.26087(3) 0.20584(3) 0.02072(11) Uani 1 1 d . . . . .
O1 O 0.28618(9) 0.39365(8) 0.40198(8) 0.0209(3) Uani 1 1 d . . . . .
C11 C 0.37359(13) 0.35407(12) 0.43663(13) 0.0223(4) Uani 1 1 d . . . . .
O2 O 0.40946(10) 0.35615(10) 0.51993(10) 0.0321(3) Uani 1 1 d . . . . .
O3 O 0.22430(8) 0.36159(8) 0.14830(8) 0.0190(3) Uani 1 1 d . . . . .
C12 C 0.13588(12) 0.40026(12) 0.11415(13) 0.0200(4) Uani 1 1 d . . . . .
O4 O 0.09820(10) 0.39606(10) 0.03112(9) 0.0287(3) Uani 1 1 d . . . . .
Si1 Si -0.09574(3) 0.59266(3) 0.26053(4) 0.01961(12) Uani 1 1 d . . . . .
C13 C -0.05438(14) 0.70988(13) 0.26401(15) 0.0280(4) Uani 1 1 d . . . . .
H3 H -0.1079 0.7479 0.2659 0.034 Uiso 1 1 calc R U . . .
C14 C 0.02630(16) 0.73044(16) 0.35280(19) 0.0438(6) Uani 1 1 d . . . . .
H4 H 0.0800 0.6936 0.3543 0.066 Uiso 1 1 calc R U . . .
H5 H 0.0066 0.7187 0.4085 0.066 Uiso 1 1 calc R U . . .
H6 H 0.0437 0.7922 0.3523 0.066 Uiso 1 1 calc R U . . .
C15 C -0.02906(19) 0.73493(15) 0.17572(19) 0.0444(6) Uani 1 1 d . . . . .
H7 H -0.0091 0.7962 0.1801 0.067 Uiso 1 1 calc R U . . .
H8 H -0.0836 0.7272 0.1205 0.067 Uiso 1 1 calc R U . . .
H9 H 0.0218 0.6974 0.1699 0.067 Uiso 1 1 calc R U . . .
C16 C -0.11575(14) 0.56421(13) 0.37603(14) 0.0260(4) Uani 1 1 d . . . . .
H10 H -0.0548 0.5741 0.4255 0.031 Uiso 1 1 calc R U . . .
C17 C -0.14157(18) 0.46845(15) 0.38545(16) 0.0384(5) Uani 1 1 d . . . . .
H11 H -0.1371 0.4561 0.4510 0.058 Uiso 1 1 calc R U . . .
H12 H -0.0986 0.4302 0.3657 0.058 Uiso 1 1 calc R U . . .
H13 H -0.2055 0.4577 0.3456 0.058 Uiso 1 1 calc R U . . .
C18 C -0.18632(19) 0.62579(18) 0.40027(18) 0.0456(6) Uani 1 1 d . . . . .
H14 H -0.2476 0.6188 0.3536 0.068 Uiso 1 1 calc R U . . .
H15 H -0.1655 0.6865 0.4000 0.068 Uiso 1 1 calc R U . . .
H16 H -0.1908 0.6112 0.4627 0.068 Uiso 1 1 calc R U . . .
C19 C -0.19548(13) 0.57200(13) 0.15065(13) 0.0239(4) Uani 1 1 d . . . . .
H17 H -0.1682 0.5751 0.0974 0.029 Uiso 1 1 calc R U . . .
C20 C -0.23880(16) 0.48085(14) 0.14551(16) 0.0355(5) Uani 1 1 d . . . . .
H18 H -0.2739 0.4768 0.1910 0.053 Uiso 1 1 calc R U . . .
H19 H -0.1893 0.4366 0.1602 0.053 Uiso 1 1 calc R U . . .
H20 H -0.2809 0.4707 0.0821 0.053 Uiso 1 1 calc R U . . .
C21 C -0.27166(15) 0.64248(15) 0.13074(16) 0.0351(5) Uani 1 1 d . . . . .
H21 H -0.3166 0.6323 0.0688 0.053 Uiso 1 1 calc R U . . .
H22 H -0.2432 0.7003 0.1319 0.053 Uiso 1 1 calc R U . . .
H23 H -0.3038 0.6398 0.1788 0.053 Uiso 1 1 calc R U . . .
Si2 Si 0.60512(3) 0.15670(3) 0.29513(4) 0.01895(12) Uani 1 1 d . . . . .
C22 C 0.56380(14) 0.03968(13) 0.29595(14) 0.0255(4) Uani 1 1 d . . . . .
H24 H 0.6172 0.0011 0.2949 0.031 Uiso 1 1 calc R U . . .
C23 C 0.48216(17) 0.01594(15) 0.20923(16) 0.0385(5) Uani 1 1 d . . . . .
H25 H 0.4668 -0.0461 0.2118 0.058 Uiso 1 1 calc R U . . .
H26 H 0.4998 0.0272 0.1523 0.058 Uiso 1 1 calc R U . . .
H27 H 0.4277 0.0516 0.2082 0.058 Uiso 1 1 calc R U . . .
C24 C 0.53912(17) 0.01740(15) 0.38580(16) 0.0377(5) Uani 1 1 d . . . . .
H28 H 0.4873 0.0544 0.3899 0.057 Uiso 1 1 calc R U . . .
H29 H 0.5935 0.0279 0.4406 0.057 Uiso 1 1 calc R U . . .
H30 H 0.5209 -0.0443 0.3843 0.057 Uiso 1 1 calc R U . . .
C25 C 0.62542(14) 0.18343(13) 0.17972(14) 0.0252(4) Uani 1 1 d . . . . .
H31 H 0.5632 0.1783 0.1311 0.030 Uiso 1 1 calc R U . . .
C26 C 0.65877(17) 0.27690(16) 0.17196(17) 0.0393(5) Uani 1 1 d . . . . .
H32 H 0.7231 0.2834 0.2126 0.059 Uiso 1 1 calc R U . . .
H33 H 0.6184 0.3183 0.1915 0.059 Uiso 1 1 calc R U . . .
H34 H 0.6562 0.2888 0.1067 0.059 Uiso 1 1 calc R U . . .
C27 C 0.6890(2) 0.11765(18) 0.15154(19) 0.0522(7) Uani 1 1 d . . . . .
H35 H 0.6904 0.1306 0.0877 0.078 Uiso 1 1 calc R U . . .
H36 H 0.6651 0.0583 0.1537 0.078 Uiso 1 1 calc R U . . .
H37 H 0.7522 0.1220 0.1952 0.078 Uiso 1 1 calc R U . . .
C28 C 0.70602(13) 0.17596(13) 0.40460(14) 0.0256(4) Uani 1 1 d . . . . .
H38 H 0.6809 0.1661 0.4586 0.031 Uiso 1 1 calc R U . . .
C29 C 0.74538(15) 0.26920(15) 0.41634(17) 0.0368(5) Uani 1 1 d . . . . .
H39 H 0.7867 0.2770 0.4805 0.055 Uiso 1 1 calc R U . . .
H40 H 0.6940 0.3113 0.4042 0.055 Uiso 1 1 calc R U . . .
H41 H 0.7807 0.2789 0.3718 0.055 Uiso 1 1 calc R U . . .
C30 C 0.78522(15) 0.10915(17) 0.41645(18) 0.0415(6) Uani 1 1 d . . . . .
H42 H 0.8124 0.1158 0.3649 0.062 Uiso 1 1 calc R U . . .
H43 H 0.7603 0.0498 0.4155 0.062 Uiso 1 1 calc R U . . .
H44 H 0.8334 0.1193 0.4765 0.062 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
S1 C4 1.7168(18) . ?
S1 C1 1.7382(19) . ?
C1 C2 1.372(3) . ?
C1 Si1 1.8871(19) . ?
C2 C3 1.407(3) . ?
C2 H1 0.9500 . ?
C3 C4 1.382(2) . ?
C3 C12 1.454(3) . ?
C4 C5 1.412(2) . ?
C5 C6 1.352(2) . ?
C5 O1 1.373(2) . ?
C6 O3 1.367(2) . ?
C6 C7 1.429(2) . ?
C7 C8 1.374(2) . ?
C7 S2 1.7153(18) . ?
C8 C9 1.402(2) . ?
C8 C11 1.455(3) . ?
C9 C10 1.378(3) . ?
C9 H2 0.9500 . ?
C10 S2 1.7433(18) . ?
C10 Si2 1.8871(18) . ?
O1 C11 1.397(2) . ?
C11 O2 1.198(2) . ?
O3 C12 1.403(2) . ?
C12 O4 1.200(2) . ?
Si1 C19 1.8869(19) . ?
Si1 C16 1.889(2) . ?
Si1 C13 1.892(2) . ?
C13 C15 1.527(3) . ?
C13 C14 1.536(3) . ?
C13 H3 1.0000 . ?
C14 H4 0.9800 . ?
C14 H5 0.9800 . ?
C14 H6 0.9800 . ?
C15 H7 0.9800 . ?
C15 H8 0.9800 . ?
C15 H9 0.9800 . ?
C16 C17 1.531(3) . ?
C16 C18 1.541(3) . ?
C16 H10 1.0000 . ?
C17 H11 0.9800 . ?
C17 H12 0.9800 . ?
C17 H13 0.9800 . ?
C18 H14 0.9800 . ?
C18 H15 0.9800 . ?
C18 H16 0.9800 . ?
C19 C20 1.530(3) . ?
C19 C21 1.535(3) . ?
C19 H17 1.0000 . ?
C20 H18 0.9800 . ?
C20 H19 0.9800 . ?
C20 H20 0.9800 . ?
C21 H21 0.9800 . ?
C21 H22 0.9800 . ?
C21 H23 0.9800 . ?
Si2 C25 1.884(2) . ?
Si2 C28 1.889(2) . ?
Si2 C22 1.894(2) . ?
C22 C24 1.534(3) . ?
C22 C23 1.536(3) . ?
C22 H24 1.0000 . ?
C23 H25 0.9800 . ?
C23 H26 0.9800 . ?
C23 H27 0.9800 . ?
C24 H28 0.9800 . ?
C24 H29 0.9800 . ?
C24 H30 0.9800 . ?
C25 C26 1.530(3) . ?
C25 C27 1.531(3) . ?
C25 H31 1.0000 . ?
C26 H32 0.9800 . ?
C26 H33 0.9800 . ?
C26 H34 0.9800 . ?
C27 H35 0.9800 . ?
C27 H36 0.9800 . ?
C27 H37 0.9800 . ?
C28 C29 1.533(3) . ?
C28 C30 1.538(3) . ?
C28 H38 1.0000 . ?
C29 H39 0.9800 . ?
C29 H40 0.9800 . ?
C29 H41 0.9800 . ?
C30 H42 0.9800 . ?
C30 H43 0.9800 . ?
C30 H44 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
C4 S1 C1 92.50(9) . . ?
C2 C1 S1 109.92(14) . . ?
C2 C1 Si1 129.26(15) . . ?
S1 C1 Si1 120.70(11) . . ?
C1 C2 C3 114.01(17) . . ?
C1 C2 H1 123.0 . . ?
C3 C2 H1 123.0 . . ?
C4 C3 C2 112.59(17) . . ?
C4 C3 C12 120.71(16) . . ?
C2 C3 C12 126.70(17) . . ?
C3 C4 C5 120.43(17) . . ?
C3 C4 S1 110.98(13) . . ?
C5 C4 S1 128.58(14) . . ?
C6 C5 O1 122.80(16) . . ?
C6 C5 C4 118.62(16) . . ?
O1 C5 C4 118.57(16) . . ?
C5 C6 O3 122.59(16) . . ?
C5 C6 C7 118.29(16) . . ?
O3 C6 C7 119.12(16) . . ?
C8 C7 C6 119.76(16) . . ?
C8 C7 S2 111.67(13) . . ?
C6 C7 S2 128.45(14) . . ?
C7 C8 C9 112.05(16) . . ?
C7 C8 C11 121.75(16) . . ?
C9 C8 C11 126.17(16) . . ?
C10 C9 C8 114.82(16) . . ?
C10 C9 H2 122.6 . . ?
C8 C9 H2 122.6 . . ?
C9 C10 S2 109.07(13) . . ?
C9 C10 Si2 129.36(14) . . ?
S2 C10 Si2 121.46(11) . . ?
C7 S2 C10 92.38(9) . . ?
C5 O1 C11 122.15(14) . . ?
O2 C11 O1 116.89(17) . . ?
O2 C11 C8 127.86(17) . . ?
O1 C11 C8 115.24(15) . . ?
C6 O3 C12 122.03(14) . . ?
O4 C12 O3 117.00(16) . . ?
O4 C12 C3 127.47(17) . . ?
O3 C12 C3 115.53(15) . . ?
C19 Si1 C1 104.76(8) . . ?
C19 Si1 C16 116.88(9) . . ?
C1 Si1 C16 107.43(8) . . ?
C19 Si1 C13 110.55(9) . . ?
C1 Si1 C13 107.12(9) . . ?
C16 Si1 C13 109.54(9) . . ?
C15 C13 C14 110.9(2) . . ?
C15 C13 Si1 112.28(15) . . ?
C14 C13 Si1 112.65(15) . . ?
C15 C13 H3 106.9 . . ?
C14 C13 H3 106.9 . . ?
Si1 C13 H3 106.9 . . ?
C13 C14 H4 109.5 . . ?
C13 C14 H5 109.5 . . ?
H4 C14 H5 109.5 . . ?
C13 C14 H6 109.5 . . ?
H4 C14 H6 109.5 . . ?
H5 C14 H6 109.5 . . ?
C13 C15 H7 109.5 . . ?
C13 C15 H8 109.5 . . ?
H7 C15 H8 109.5 . . ?
C13 C15 H9 109.5 . . ?
H7 C15 H9 109.5 . . ?
H8 C15 H9 109.5 . . ?
C17 C16 C18 110.50(19) . . ?
C17 C16 Si1 114.74(14) . . ?
C18 C16 Si1 112.61(14) . . ?
C17 C16 H10 106.1 . . ?
C18 C16 H10 106.1 . . ?
Si1 C16 H10 106.1 . . ?
C16 C17 H11 109.5 . . ?
C16 C17 H12 109.5 . . ?
H11 C17 H12 109.5 . . ?
C16 C17 H13 109.5 . . ?
H11 C17 H13 109.5 . . ?
H12 C17 H13 109.5 . . ?
C16 C18 H14 109.5 . . ?
C16 C18 H15 109.5 . . ?
H14 C18 H15 109.5 . . ?
C16 C18 H16 109.5 . . ?
H14 C18 H16 109.5 . . ?
H15 C18 H16 109.5 . . ?
C20 C19 C21 110.31(17) . . ?
C20 C19 Si1 114.27(14) . . ?
C21 C19 Si1 113.75(14) . . ?
C20 C19 H17 105.9 . . ?
C21 C19 H17 105.9 . . ?
Si1 C19 H17 105.9 . . ?
C19 C20 H18 109.5 . . ?
C19 C20 H19 109.5 . . ?
H18 C20 H19 109.5 . . ?
C19 C20 H20 109.5 . . ?
H18 C20 H20 109.5 . . ?
H19 C20 H20 109.5 . . ?
C19 C21 H21 109.5 . . ?
C19 C21 H22 109.5 . . ?
H21 C21 H22 109.5 . . ?
C19 C21 H23 109.5 . . ?
H21 C21 H23 109.5 . . ?
H22 C21 H23 109.5 . . ?
C25 Si2 C10 106.16(8) . . ?
C25 Si2 C28 116.66(9) . . ?
C10 Si2 C28 106.16(8) . . ?
C25 Si2 C22 110.76(9) . . ?
C10 Si2 C22 107.92(9) . . ?
C28 Si2 C22 108.73(9) . . ?
C24 C22 C23 110.02(18) . . ?
C24 C22 Si2 112.42(15) . . ?
C23 C22 Si2 113.46(14) . . ?
C24 C22 H24 106.8 . . ?
C23 C22 H24 106.8 . . ?
Si2 C22 H24 106.8 . . ?
C22 C23 H25 109.5 . . ?
C22 C23 H26 109.5 . . ?
H25 C23 H26 109.5 . . ?
C22 C23 H27 109.5 . . ?
H25 C23 H27 109.5 . . ?
H26 C23 H27 109.5 . . ?
C22 C24 H28 109.5 . . ?
C22 C24 H29 109.5 . . ?
H28 C24 H29 109.5 . . ?
C22 C24 H30 109.5 . . ?
H28 C24 H30 109.5 . . ?
H29 C24 H30 109.5 . . ?
C26 C25 C27 110.25(19) . . ?
C26 C25 Si2 114.77(15) . . ?
C27 C25 Si2 113.32(15) . . ?
C26 C25 H31 105.9 . . ?
C27 C25 H31 105.9 . . ?
Si2 C25 H31 105.9 . . ?
C25 C26 H32 109.5 . . ?
C25 C26 H33 109.5 . . ?
H32 C26 H33 109.5 . . ?
C25 C26 H34 109.5 . . ?
H32 C26 H34 109.5 . . ?
H33 C26 H34 109.5 . . ?
C25 C27 H35 109.5 . . ?
C25 C27 H36 109.5 . . ?
H35 C27 H36 109.5 . . ?
C25 C27 H37 109.5 . . ?
H35 C27 H37 109.5 . . ?
H36 C27 H37 109.5 . . ?
C29 C28 C30 110.16(17) . . ?
C29 C28 Si2 115.21(14) . . ?
C30 C28 Si2 112.87(15) . . ?
C29 C28 H38 105.9 . . ?
C30 C28 H38 105.9 . . ?
Si2 C28 H38 105.9 . . ?
C28 C29 H39 109.5 . . ?
C28 C29 H40 109.5 . . ?
H39 C29 H40 109.5 . . ?
C28 C29 H41 109.5 . . ?
H39 C29 H41 109.5 . . ?
H40 C29 H41 109.5 . . ?
C28 C30 H42 109.5 . . ?
C28 C30 H43 109.5 . . ?
H42 C30 H43 109.5 . . ?
C28 C30 H44 109.5 . . ?
H42 C30 H44 109.5 . . ?
H43 C30 H44 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
C4 S1 C1 C2 0.47(15) . . . . ?
C4 S1 C1 Si1 -175.98(12) . . . . ?
S1 C1 C2 C3 0.0(2) . . . . ?
Si1 C1 C2 C3 176.01(14) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C1 C2 C3 C12 179.95(18) . . . . ?
C2 C3 C4 C5 -178.00(16) . . . . ?
C12 C3 C4 C5 1.5(3) . . . . ?
C2 C3 C4 S1 0.9(2) . . . . ?
C12 C3 C4 S1 -179.58(14) . . . . ?
C1 S1 C4 C3 -0.78(14) . . . . ?
C1 S1 C4 C5 178.00(17) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
S1 C4 C5 C6 -178.02(14) . . . . ?
C3 C4 C5 O1 179.60(16) . . . . ?
S1 C4 C5 O1 0.9(3) . . . . ?
O1 C5 C6 O3 -179.87(15) . . . . ?
C4 C5 C6 O3 -1.0(3) . . . . ?
O1 C5 C6 C7 0.7(3) . . . . ?
C4 C5 C6 C7 179.55(16) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
O3 C6 C7 C8 -179.61(16) . . . . ?
C5 C6 C7 S2 175.76(14) . . . . ?
O3 C6 C7 S2 -3.7(3) . . . . ?
C6 C7 C8 C9 176.90(16) . . . . ?
S2 C7 C8 C9 0.4(2) . . . . ?
C6 C7 C8 C11 -0.9(3) . . . . ?
S2 C7 C8 C11 -177.40(14) . . . . ?
C7 C8 C9 C10 -1.0(2) . . . . ?
C11 C8 C9 C10 176.72(18) . . . . ?
C8 C9 C10 S2 1.1(2) . . . . ?
C8 C9 C10 Si2 -175.19(14) . . . . ?
C8 C7 S2 C10 0.18(15) . . . . ?
C6 C7 S2 C10 -175.96(17) . . . . ?
C9 C10 S2 C7 -0.69(15) . . . . ?
Si2 C10 S2 C7 175.90(12) . . . . ?
C6 C5 O1 C11 -0.2(3) . . . . ?
C4 C5 O1 C11 -179.08(16) . . . . ?
C5 O1 C11 O2 179.95(17) . . . . ?
C5 O1 C11 C8 -0.8(2) . . . . ?
C7 C8 C11 O2 -179.5(2) . . . . ?
C9 C8 C11 O2 3.0(3) . . . . ?
C7 C8 C11 O1 1.3(3) . . . . ?
C9 C8 C11 O1 -176.16(17) . . . . ?
C5 C6 O3 C12 -1.0(3) . . . . ?
C7 C6 O3 C12 178.48(15) . . . . ?
C6 O3 C12 O4 -177.45(16) . . . . ?
C6 O3 C12 C3 3.0(2) . . . . ?
C4 C3 C12 O4 177.26(19) . . . . ?
C2 C3 C12 O4 -3.3(3) . . . . ?
C4 C3 C12 O3 -3.3(2) . . . . ?
C2 C3 C12 O3 176.19(16) . . . . ?
C2 C1 Si1 C19 24.9(2) . . . . ?
S1 C1 Si1 C19 -159.47(11) . . . . ?
C2 C1 Si1 C16 149.79(18) . . . . ?
S1 C1 Si1 C16 -34.53(14) . . . . ?
C2 C1 Si1 C13 -92.60(19) . . . . ?
S1 C1 Si1 C13 83.08(13) . . . . ?
C19 Si1 C13 C15 -54.57(18) . . . . ?
C1 Si1 C13 C15 59.01(17) . . . . ?
C16 Si1 C13 C15 175.23(15) . . . . ?
C19 Si1 C13 C14 179.40(15) . . . . ?
C1 Si1 C13 C14 -67.01(18) . . . . ?
C16 Si1 C13 C14 49.21(18) . . . . ?
C19 Si1 C16 C17 58.24(18) . . . . ?
C1 Si1 C16 C17 -59.04(17) . . . . ?
C13 Si1 C16 C17 -175.07(15) . . . . ?
C19 Si1 C16 C18 -69.31(19) . . . . ?
C1 Si1 C16 C18 173.40(16) . . . . ?
C13 Si1 C16 C18 57.38(18) . . . . ?
C1 Si1 C19 C20 69.62(16) . . . . ?
C16 Si1 C19 C20 -49.11(18) . . . . ?
C13 Si1 C19 C20 -175.30(15) . . . . ?
C1 Si1 C19 C21 -162.48(15) . . . . ?
C16 Si1 C19 C21 78.79(17) . . . . ?
C13 Si1 C19 C21 -47.40(18) . . . . ?
C9 C10 Si2 C25 -149.27(18) . . . . ?
S2 C10 Si2 C25 34.90(14) . . . . ?
C9 C10 Si2 C28 -24.5(2) . . . . ?
S2 C10 Si2 C28 159.68(11) . . . . ?
C9 C10 Si2 C22 91.94(19) . . . . ?
S2 C10 Si2 C22 -83.89(13) . . . . ?
C25 Si2 C22 C24 -175.53(14) . . . . ?
C10 Si2 C22 C24 -59.72(16) . . . . ?
C28 Si2 C22 C24 55.03(17) . . . . ?
C25 Si2 C22 C23 -49.89(18) . . . . ?
C10 Si2 C22 C23 65.92(18) . . . . ?
C28 Si2 C22 C23 -179.33(16) . . . . ?
C10 Si2 C25 C26 62.92(17) . . . . ?
C28 Si2 C25 C26 -55.10(18) . . . . ?
C22 Si2 C25 C26 179.82(15) . . . . ?
C10 Si2 C25 C27 -169.20(17) . . . . ?
C28 Si2 C25 C27 72.8(2) . . . . ?
C22 Si2 C25 C27 -52.30(19) . . . . ?
C25 Si2 C28 C29 56.05(18) . . . . ?
C10 Si2 C28 C29 -61.97(17) . . . . ?
C22 Si2 C28 C29 -177.86(15) . . . . ?
C25 Si2 C28 C30 -71.69(18) . . . . ?
C10 Si2 C28 C30 170.29(16) . . . . ?
C22 Si2 C28 C30 54.41(18) . . . . ?

_refine_diff_density_max         0.865
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.057



####################################################################### 
# 
# 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_3d
_audit_block_doi                 10.5517/ccdc.csd.cc20dscl
_database_code_depnum_ccdc_archive 'CCDC 1859329'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.orglett.8b03169 2018
loop_
_audit_author_name
_audit_author_address
'Yosuke Tani'
;Osaka University
Japan
;
_audit_update_record             
;
2018-07-31 deposited with the CCDC.	2021-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H4 O4 S2'
_chemical_formula_weight         276.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   3.7775(8)
_cell_length_b                   7.0673(13)
_cell_length_c                   9.5332(18)
_cell_angle_alpha                86.303(6)
_cell_angle_beta                 88.614(6)
_cell_angle_gamma                83.243(6)
_cell_volume                     252.18(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    1188
_cell_measurement_theta_min      3.505
_cell_measurement_theta_max      27.245

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_F_000             140
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.529
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3395
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'Rigaku VariMax RAPID II'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2386
_diffrn_reflns_av_unetI/netI     0.1465
_diffrn_reflns_av_R_equivalents  0.0960
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.504
_diffrn_reflns_theta_max         27.466
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1138
_reflns_number_gt                644
_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       'Rigaku RAPID AUTO'
_computing_cell_refinement       'Rigaku RAPID AUTO'
_computing_data_reduction        'Rigaku RAPID AUTO'
_computing_structure_solution    Yadokari-SG
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_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)+(0.0835P)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         1138
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1312
_refine_ls_R_factor_gt           0.0649
_refine_ls_wR_factor_ref         0.1647
_refine_ls_wR_factor_gt          0.1417
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_restrained_S_all      0.934
_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 0.7467(4) 0.58922(18) 0.33565(15) 0.0276(4) Uani 1 1 d . . . . .
C1 C 0.6023(13) 0.6239(7) 0.1640(5) 0.0275(12) Uani 1 1 d . . . . .
H1 H 0.6442 0.5292 0.0973 0.033 Uiso 1 1 calc R U . . .
C2 C 0.4236(13) 0.7991(6) 0.1340(5) 0.0281(13) Uani 1 1 d . . . . .
H2 H 0.3264 0.8413 0.0449 0.034 Uiso 1 1 calc R U . . .
C3 C 0.3998(13) 0.9129(6) 0.2541(5) 0.0278(12) Uani 1 1 d . . . . .
C4 C 0.5670(13) 0.8152(6) 0.3699(5) 0.0256(12) Uani 1 1 d . . . . .
C5 C 0.5778(13) 0.9097(6) 0.4982(5) 0.0239(11) Uani 1 1 d . . . . .
O1 O 0.7485(9) 0.8114(4) 0.6109(3) 0.0282(9) Uani 1 1 d . . . . .
C6 C 0.7753(14) 0.8959(7) 0.7388(5) 0.0275(12) Uani 1 1 d . . . . .
O2 O 0.9443(10) 0.7982(5) 0.8298(4) 0.0337(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
S1 C4 1.709(4) . ?
S1 C1 1.731(5) . ?
C1 C2 1.356(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.436(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(6) . ?
C3 C6 1.438(7) 2_676 ?
C4 C5 1.435(6) . ?
C5 C5 1.343(9) 2_676 ?
C5 O1 1.374(5) . ?
O1 C6 1.402(6) . ?
C6 O2 1.218(5) . ?
C6 C3 1.438(7) 2_676 ?

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 C1 90.7(2) . . ?
C2 C1 S1 113.5(4) . . ?
C2 C1 H1 123.2 . . ?
S1 C1 H1 123.2 . . ?
C1 C2 C3 111.4(4) . . ?
C1 C2 H2 124.3 . . ?
C3 C2 H2 124.3 . . ?
C4 C3 C2 111.8(4) . . ?
C4 C3 C6 121.6(4) . 2_676 ?
C2 C3 C6 126.6(4) . 2_676 ?
C3 C4 C5 119.3(4) . . ?
C3 C4 S1 112.6(4) . . ?
C5 C4 S1 128.1(4) . . ?
C5 C5 O1 123.3(5) 2_676 . ?
C5 C5 C4 118.4(5) 2_676 . ?
O1 C5 C4 118.4(4) . . ?
C5 O1 C6 121.5(3) . . ?
O2 C6 O1 115.9(4) . . ?
O2 C6 C3 128.1(5) . 2_676 ?
O1 C6 C3 115.9(4) . 2_676 ?

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
C4 S1 C1 C2 -0.3(4) . . . . ?
S1 C1 C2 C3 0.0(6) . . . . ?
C1 C2 C3 C4 0.3(7) . . . . ?
C1 C2 C3 C6 -178.9(5) . . . 2_676 ?
C2 C3 C4 C5 178.2(5) . . . . ?
C6 C3 C4 C5 -2.5(8) 2_676 . . . ?
C2 C3 C4 S1 -0.6(6) . . . . ?
C6 C3 C4 S1 178.7(4) 2_676 . . . ?
C1 S1 C4 C3 0.5(4) . . . . ?
C1 S1 C4 C5 -178.2(5) . . . . ?
C3 C4 C5 C5 0.5(9) . . . 2_676 ?
S1 C4 C5 C5 179.1(5) . . . 2_676 ?
C3 C4 C5 O1 -179.2(4) . . . . ?
S1 C4 C5 O1 -0.6(7) . . . . ?
C5 C5 O1 C6 -0.9(9) 2_676 . . . ?
C4 C5 O1 C6 178.8(4) . . . . ?
C5 O1 C6 O2 -177.2(5) . . . . ?
C5 O1 C6 C3 2.7(7) . . . 2_676 ?

_refine_diff_density_max         0.448
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.112



####################################################################### 
# 
# 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_4e
_audit_block_doi                 10.5517/ccdc.csd.cc20dsgp
_database_code_depnum_ccdc_archive 'CCDC 1859332'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.orglett.8b03169 2018
loop_
_audit_author_name
_audit_author_address
'Yosuke Tani'
;Osaka University
Japan
;
_audit_update_record             
;
2018-07-31 deposited with the CCDC.	2021-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H44 O4 S2 Si2'
_chemical_formula_weight         588.95

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.18500(10)
_cell_length_b                   15.9844(3)
_cell_length_c                   11.9420(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.363(7)
_cell_angle_gamma                90
_cell_volume                     1552.77(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    19722
_cell_measurement_theta_min      3.075
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.282
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8927
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'R-AXIS7 FR-E'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25375
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.073
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3561
_reflns_number_gt                3157
_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       'Rigaku RAPID AUTO'
_computing_cell_refinement       'Rigaku RAPID AUTO'
_computing_data_reduction        'Rigaku RAPID AUTO'
_computing_structure_solution    Yadokari-SG
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_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)+(0.0455P)²+0.7138P] 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         3561
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0932
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
C1 C 0.63009(19) 0.25572(9) 0.90582(12) 0.0210(3) Uani 1 1 d . . . . .
C2 C 0.46073(19) 0.24859(9) 0.88847(12) 0.0223(3) Uani 1 1 d . . . . .
H1 H 0.3885 0.2929 0.8631 0.027 Uiso 1 1 calc R U . . .
C3 C 0.40869(19) 0.16680(9) 0.91336(13) 0.0214(3) Uani 1 1 d . . . . .
C4 C 0.53448(18) 0.11407(9) 0.94994(12) 0.0201(3) Uani 1 1 d . . . . .
S1 S 0.72068(5) 0.16144(2) 0.95328(3) 0.02374(11) Uani 1 1 d . . . . .
C5 C 0.46641(18) 0.03530(9) 0.97829(13) 0.0206(3) Uani 1 1 d . . . . .
O1 O 0.29712(13) 0.04015(6) 0.95544(10) 0.0245(2) Uani 1 1 d . . . . .
C6 C 0.25471(19) 0.12138(10) 0.91503(14) 0.0251(3) Uani 1 1 d . . . . .
O2 O 0.11427(15) 0.13942(8) 0.89092(12) 0.0379(3) Uani 1 1 d . . . . .
Si1 Si 0.75891(5) 0.35162(2) 0.88583(4) 0.01967(11) Uani 1 1 d . . . . .
C7 C 0.8466(2) 0.39009(10) 1.02927(14) 0.0284(3) Uani 1 1 d . . . . .
H2 H 0.9084 0.4427 1.0170 0.034 Uiso 1 1 calc R U . . .
C8 C 0.9687(3) 0.32958(13) 1.09151(17) 0.0462(5) Uani 1 1 d . . . . .
H3 H 1.0117 0.3538 1.1643 0.069 Uiso 1 1 calc R U . . .
H4 H 1.0596 0.3195 1.0463 0.069 Uiso 1 1 calc R U . . .
H5 H 0.9133 0.2766 1.1040 0.069 Uiso 1 1 calc R U . . .
C9 C 0.7117(3) 0.41330(13) 1.10249(17) 0.0458(5) Uani 1 1 d . . . . .
H6 H 0.6475 0.3633 1.1163 0.069 Uiso 1 1 calc R U . . .
H7 H 0.6394 0.4555 1.0637 0.069 Uiso 1 1 calc R U . . .
H8 H 0.7618 0.4359 1.1745 0.069 Uiso 1 1 calc R U . . .
C10 C 0.9326(2) 0.31926(10) 0.80533(14) 0.0264(3) Uani 1 1 d . . . . .
H9 H 1.0000 0.2786 0.8546 0.032 Uiso 1 1 calc R U . . .
C11 C 1.0478(2) 0.39184(13) 0.78482(19) 0.0428(5) Uani 1 1 d . . . . .
H10 H 1.1422 0.3705 0.7497 0.064 Uiso 1 1 calc R U . . .
H11 H 1.0864 0.4185 0.8568 0.064 Uiso 1 1 calc R U . . .
H12 H 0.9885 0.4330 0.7348 0.064 Uiso 1 1 calc R U . . .
C12 C 0.8788(3) 0.27274(12) 0.69550(16) 0.0393(4) Uani 1 1 d . . . . .
H13 H 0.8143 0.3104 0.6430 0.059 Uiso 1 1 calc R U . . .
H14 H 0.8115 0.2244 0.7113 0.059 Uiso 1 1 calc R U . . .
H15 H 0.9761 0.2537 0.6618 0.059 Uiso 1 1 calc R U . . .
C13 C 0.6140(2) 0.43281(9) 0.81694(15) 0.0279(3) Uani 1 1 d . . . . .
H16 H 0.5176 0.4342 0.8616 0.033 Uiso 1 1 calc R U . . .
C14 C 0.6876(2) 0.52131(11) 0.8238(2) 0.0423(5) Uani 1 1 d . . . . .
H17 H 0.7842 0.5231 0.7822 0.063 Uiso 1 1 calc R U . . .
H18 H 0.7201 0.5359 0.9029 0.063 Uiso 1 1 calc R U . . .
H19 H 0.6055 0.5614 0.7908 0.063 Uiso 1 1 calc R U . . .
C15 C 0.5445(3) 0.41391(12) 0.69564(17) 0.0422(5) Uani 1 1 d . . . . .
H20 H 0.4545 0.4528 0.6723 0.063 Uiso 1 1 calc R U . . .
H21 H 0.5031 0.3564 0.6907 0.063 Uiso 1 1 calc R U . . .
H22 H 0.6313 0.4205 0.6460 0.063 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
C1 C2 1.383(2) . ?
C1 S1 1.7461(15) . ?
C1 Si1 1.8905(15) . ?
C2 C3 1.417(2) . ?
C2 H1 0.9500 . ?
C3 C4 1.364(2) . ?
C3 C6 1.457(2) . ?
C4 C5 1.4325(19) . ?
C4 S1 1.6983(15) . ?
C5 C5 1.335(3) 3_657 ?
C5 O1 1.3844(18) . ?
O1 C6 1.4149(18) . ?
C6 O2 1.1891(19) . ?
Si1 C10 1.8753(16) . ?
Si1 C13 1.8848(16) . ?
Si1 C7 1.8854(17) . ?
C7 C8 1.524(3) . ?
C7 C9 1.528(3) . ?
C7 H2 1.0000 . ?
C8 H3 0.9800 . ?
C8 H4 0.9800 . ?
C8 H5 0.9800 . ?
C9 H6 0.9800 . ?
C9 H7 0.9800 . ?
C9 H8 0.9800 . ?
C10 C12 1.529(2) . ?
C10 C11 1.532(2) . ?
C10 H9 1.0000 . ?
C11 H10 0.9800 . ?
C11 H11 0.9800 . ?
C11 H12 0.9800 . ?
C12 H13 0.9800 . ?
C12 H14 0.9800 . ?
C12 H15 0.9800 . ?
C13 C15 1.527(3) . ?
C13 C14 1.536(2) . ?
C13 H16 1.0000 . ?
C14 H17 0.9800 . ?
C14 H18 0.9800 . ?
C14 H19 0.9800 . ?
C15 H20 0.9800 . ?
C15 H21 0.9800 . ?
C15 H22 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
C2 C1 S1 111.10(11) . . ?
C2 C1 Si1 127.70(11) . . ?
S1 C1 Si1 121.20(9) . . ?
C1 C2 C3 111.35(14) . . ?
C1 C2 H1 124.3 . . ?
C3 C2 H1 124.3 . . ?
C4 C3 C2 113.80(14) . . ?
C4 C3 C6 108.13(13) . . ?
C2 C3 C6 138.03(14) . . ?
C3 C4 C5 108.61(13) . . ?
C3 C4 S1 112.05(11) . . ?
C5 C4 S1 139.28(12) . . ?
C4 S1 C1 91.69(7) . . ?
C5 C5 O1 118.95(17) 3_657 . ?
C5 C5 C4 132.90(18) 3_657 . ?
O1 C5 C4 108.13(12) . . ?
C5 O1 C6 108.72(11) . . ?
O2 C6 O1 119.94(14) . . ?
O2 C6 C3 133.68(15) . . ?
O1 C6 C3 106.38(12) . . ?
C10 Si1 C13 116.26(8) . . ?
C10 Si1 C7 108.78(8) . . ?
C13 Si1 C7 109.26(8) . . ?
C10 Si1 C1 107.84(7) . . ?
C13 Si1 C1 106.29(7) . . ?
C7 Si1 C1 108.13(7) . . ?
C8 C7 C9 110.57(17) . . ?
C8 C7 Si1 113.52(12) . . ?
C9 C7 Si1 111.89(13) . . ?
C8 C7 H2 106.8 . . ?
C9 C7 H2 106.8 . . ?
Si1 C7 H2 106.8 . . ?
C7 C8 H3 109.5 . . ?
C7 C8 H4 109.5 . . ?
H3 C8 H4 109.5 . . ?
C7 C8 H5 109.5 . . ?
H3 C8 H5 109.5 . . ?
H4 C8 H5 109.5 . . ?
C7 C9 H6 109.5 . . ?
C7 C9 H7 109.5 . . ?
H6 C9 H7 109.5 . . ?
C7 C9 H8 109.5 . . ?
H6 C9 H8 109.5 . . ?
H7 C9 H8 109.5 . . ?
C12 C10 C11 110.80(15) . . ?
C12 C10 Si1 114.26(12) . . ?
C11 C10 Si1 112.84(12) . . ?
C12 C10 H9 106.1 . . ?
C11 C10 H9 106.1 . . ?
Si1 C10 H9 106.1 . . ?
C10 C11 H10 109.5 . . ?
C10 C11 H11 109.5 . . ?
H10 C11 H11 109.5 . . ?
C10 C11 H12 109.5 . . ?
H10 C11 H12 109.5 . . ?
H11 C11 H12 109.5 . . ?
C10 C12 H13 109.5 . . ?
C10 C12 H14 109.5 . . ?
H13 C12 H14 109.5 . . ?
C10 C12 H15 109.5 . . ?
H13 C12 H15 109.5 . . ?
H14 C12 H15 109.5 . . ?
C15 C13 C14 109.62(15) . . ?
C15 C13 Si1 115.36(12) . . ?
C14 C13 Si1 112.73(12) . . ?
C15 C13 H16 106.1 . . ?
C14 C13 H16 106.1 . . ?
Si1 C13 H16 106.1 . . ?
C13 C14 H17 109.5 . . ?
C13 C14 H18 109.5 . . ?
H17 C14 H18 109.5 . . ?
C13 C14 H19 109.5 . . ?
H17 C14 H19 109.5 . . ?
H18 C14 H19 109.5 . . ?
C13 C15 H20 109.5 . . ?
C13 C15 H21 109.5 . . ?
H20 C15 H21 109.5 . . ?
C13 C15 H22 109.5 . . ?
H20 C15 H22 109.5 . . ?
H21 C15 H22 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
S1 C1 C2 C3 -0.37(16) . . . . ?
Si1 C1 C2 C3 -179.49(11) . . . . ?
C1 C2 C3 C4 0.87(19) . . . . ?
C1 C2 C3 C6 178.21(18) . . . . ?
C2 C3 C4 C5 176.77(13) . . . . ?
C6 C3 C4 C5 -1.36(18) . . . . ?
C2 C3 C4 S1 -0.97(17) . . . . ?
C6 C3 C4 S1 -179.10(11) . . . . ?
C3 C4 S1 C1 0.63(12) . . . . ?
C5 C4 S1 C1 -176.09(18) . . . . ?
C2 C1 S1 C4 -0.13(12) . . . . ?
Si1 C1 S1 C4 179.04(9) . . . . ?
C3 C4 C5 C5 -176.8(2) . . . 3_657 ?
S1 C4 C5 C5 0.0(4) . . . 3_657 ?
C3 C4 C5 O1 1.62(17) . . . . ?
S1 C4 C5 O1 178.41(13) . . . . ?
C5 C5 O1 C6 177.45(18) 3_657 . . . ?
C4 C5 O1 C6 -1.22(16) . . . . ?
C5 O1 C6 O2 -179.42(15) . . . . ?
C5 O1 C6 C3 0.40(16) . . . . ?
C4 C3 C6 O2 -179.60(19) . . . . ?
C2 C3 C6 O2 3.0(3) . . . . ?
C4 C3 C6 O1 0.62(17) . . . . ?
C2 C3 C6 O1 -176.82(17) . . . . ?
C2 C1 Si1 C10 -133.38(14) . . . . ?
S1 C1 Si1 C10 47.59(11) . . . . ?
C2 C1 Si1 C13 -8.05(16) . . . . ?
S1 C1 Si1 C13 172.92(9) . . . . ?
C2 C1 Si1 C7 109.16(14) . . . . ?
S1 C1 Si1 C7 -69.87(11) . . . . ?
C10 Si1 C7 C8 -50.93(15) . . . . ?
C13 Si1 C7 C8 -178.80(13) . . . . ?
C1 Si1 C7 C8 65.93(15) . . . . ?
C10 Si1 C7 C9 -176.94(12) . . . . ?
C13 Si1 C7 C9 55.19(14) . . . . ?
C1 Si1 C7 C9 -60.09(14) . . . . ?
C13 Si1 C10 C12 -66.27(14) . . . . ?
C7 Si1 C10 C12 169.94(12) . . . . ?
C1 Si1 C10 C12 52.90(14) . . . . ?
C13 Si1 C10 C11 61.50(15) . . . . ?
C7 Si1 C10 C11 -62.29(14) . . . . ?
C1 Si1 C10 C11 -179.33(13) . . . . ?
C10 Si1 C13 C15 51.31(15) . . . . ?
C7 Si1 C13 C15 174.85(13) . . . . ?
C1 Si1 C13 C15 -68.70(14) . . . . ?
C10 Si1 C13 C14 -75.66(15) . . . . ?
C7 Si1 C13 C14 47.88(15) . . . . ?
C1 Si1 C13 C14 164.33(13) . . . . ?

_refine_diff_density_max         0.344
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.048



