# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2015

####################################################################### 
# 
# 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_cd212331
_database_code_depnum_ccdc_archive 'CCDC 1021338'
_audit_update_record             
;
2014-08-27 deposited with the CCDC.
2015-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H33 N O3 S Si'
_chemical_formula_weight         479.69

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   10.8466(8)
_cell_length_b                   23.0405(16)
_cell_length_c                   10.6995(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.6580(10)
_cell_angle_gamma                90.00
_cell_volume                     2608.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4112
_cell_measurement_theta_min      5.156
_cell_measurement_theta_max      48.324

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.145
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.61847
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15701
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5133
_reflns_number_gt                3865
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0674P)²+0.5602P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5133
_refine_ls_number_parameters     323
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1329
_refine_ls_wR_factor_gt          0.1218
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.037
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.78622(5) 0.59345(2) 0.48326(5) 0.05277(17) Uani 1 1 d . . .
Si1 Si 0.91973(6) 0.66881(3) -0.02216(6) 0.05639(19) Uani 1 1 d . . .
N1 N 0.75043(15) 0.64481(7) 0.37099(15) 0.0475(4) Uani 1 1 d . . .
O1 O 1.03977(15) 0.60801(8) 0.18064(17) 0.0753(5) Uani 1 1 d D . .
O2 O 0.92068(14) 0.59252(7) 0.52171(16) 0.0700(5) Uani 1 1 d . . .
O3 O 0.71262(16) 0.60595(7) 0.57543(14) 0.0684(4) Uani 1 1 d . . .
C1 C 0.83725(19) 0.65384(9) 0.2846(2) 0.0521(5) Uani 1 1 d . A .
H1A H 0.9232 0.6474 0.3318 0.063 Uiso 1 1 calc R . .
H1B H 0.8309 0.6938 0.2554 0.063 Uiso 1 1 calc R . .
C2 C 0.8103(2) 0.61436(8) 0.17013(19) 0.0500(5) Uani 1 1 d . . .
C3 C 0.6938(2) 0.59269(9) 0.13136(19) 0.0522(5) Uani 1 1 d . A .
C4 C 0.59155(19) 0.61612(9) 0.18811(19) 0.0502(5) Uani 1 1 d . . .
C5 C 0.4616(2) 0.61170(10) 0.1265(2) 0.0639(6) Uani 1 1 d . A .
H5 H 0.4383 0.5915 0.0498 0.077 Uiso 1 1 calc R . .
C6 C 0.3708(2) 0.63680(12) 0.1789(3) 0.0714(7) Uani 1 1 d . . .
H6 H 0.2864 0.6325 0.1375 0.086 Uiso 1 1 calc R A .
C7 C 0.4005(2) 0.66884(10) 0.2931(3) 0.0630(6) Uani 1 1 d . A .
C8 C 0.3065(2) 0.69761(13) 0.3453(3) 0.0833(9) Uani 1 1 d . . .
H8 H 0.2216 0.6941 0.3053 0.100 Uiso 1 1 calc R A .
C9 C 0.3408(3) 0.73000(13) 0.4531(4) 0.0914(10) Uani 1 1 d . A .
H9 H 0.2789 0.7485 0.4865 0.110 Uiso 1 1 calc R . .
C10 C 0.4665(3) 0.73596(11) 0.5141(3) 0.0780(8) Uani 1 1 d . . .
H10 H 0.4882 0.7592 0.5867 0.094 Uiso 1 1 calc R A .
C11 C 0.5588(2) 0.70826(9) 0.4692(2) 0.0610(6) Uani 1 1 d . A .
H11 H 0.6427 0.7120 0.5126 0.073 Uiso 1 1 calc R . .
C12 C 0.52844(19) 0.67379(8) 0.3572(2) 0.0522(5) Uani 1 1 d . . .
C13 C 0.62060(17) 0.64489(8) 0.30361(19) 0.0454(4) Uani 1 1 d . A .
C14 C 0.6582(3) 0.54746(12) 0.0273(3) 0.0811(8) Uani 1 1 d . . .
H14A H 0.6187 0.5660 -0.0516 0.122 Uiso 1 1 calc R A .
H14B H 0.6005 0.5201 0.0510 0.122 Uiso 1 1 calc R . .
H14C H 0.7328 0.5275 0.0165 0.122 Uiso 1 1 calc R . .
C15 C 0.9160(2) 0.60821(9) 0.0991(2) 0.0563(5) Uani 1 1 d . A .
H15 H 0.9042 0.5713 0.0524 0.068 Uiso 1 1 calc R . .
C16 C 1.0841(5) 0.5621(2) 0.2664(4) 0.0728(11) Uani 0.70 1 d PDU A 1
H16A H 1.0176 0.5491 0.3073 0.087 Uiso 0.70 1 calc PR A 1
H16B H 1.1549 0.5752 0.3324 0.087 Uiso 0.70 1 calc PR A 1
C17 C 1.1237(10) 0.5144(3) 0.1933(7) 0.102(2) Uani 0.60 1 d PU A 1
H17A H 1.0505 0.4967 0.1404 0.153 Uiso 0.60 1 calc PR A 1
H17B H 1.1692 0.4861 0.2514 0.153 Uiso 0.60 1 calc PR A 1
H17C H 1.1773 0.5293 0.1403 0.153 Uiso 0.60 1 calc PR A 1
C16' C 1.0451(11) 0.5393(5) 0.1942(14) 0.086(3) Uani 0.30 1 d PDU A 2
H16C H 0.9866 0.5258 0.2447 0.104 Uiso 0.30 1 calc PR A 2
H16D H 1.0245 0.5209 0.1108 0.104 Uiso 0.30 1 calc PR A 2
C17' C 1.1772(11) 0.5268(6) 0.2600(12) 0.109(4) Uani 0.40 1 d PU A 2
H17D H 1.2318 0.5331 0.2018 0.164 Uiso 0.40 1 calc PR A 2
H17E H 1.1838 0.4871 0.2882 0.164 Uiso 0.40 1 calc PR A 2
H17F H 1.2016 0.5520 0.3326 0.164 Uiso 0.40 1 calc PR A 2
C18 C 0.9706(3) 0.73775(11) 0.0638(3) 0.0774(7) Uani 1 1 d . . .
H18A H 0.9940 0.7652 0.0056 0.116 Uiso 1 1 calc R . .
H18B H 1.0418 0.7304 0.1330 0.116 Uiso 1 1 calc R . .
H18C H 0.9023 0.7533 0.0973 0.116 Uiso 1 1 calc R . .
C19 C 0.7607(2) 0.67649(12) -0.1287(2) 0.0761(7) Uani 1 1 d . . .
H19A H 0.6995 0.6837 -0.0779 0.114 Uiso 1 1 calc R . .
H19B H 0.7393 0.6414 -0.1770 0.114 Uiso 1 1 calc R . .
H19C H 0.7611 0.7084 -0.1864 0.114 Uiso 1 1 calc R . .
C20 C 1.0361(3) 0.64652(13) -0.1175(3) 0.0844(8) Uani 1 1 d . . .
H20A H 1.0446 0.6769 -0.1764 0.127 Uiso 1 1 calc R . .
H20B H 1.0072 0.6118 -0.1643 0.127 Uiso 1 1 calc R . .
H20C H 1.1164 0.6394 -0.0610 0.127 Uiso 1 1 calc R . .
C21 C 0.73367(19) 0.52558(9) 0.41557(18) 0.0480(5) Uani 1 1 d . . .
C22 C 0.8199(2) 0.48599(9) 0.3890(2) 0.0558(5) Uani 1 1 d . . .
H22 H 0.9055 0.4951 0.4052 0.067 Uiso 1 1 calc R . .
C23 C 0.7778(2) 0.43288(10) 0.3382(2) 0.0624(6) Uani 1 1 d . . .
H23 H 0.8363 0.4061 0.3213 0.075 Uiso 1 1 calc R . .
C24 C 0.6517(2) 0.41819(9) 0.3116(2) 0.0590(6) Uani 1 1 d . . .
C25 C 0.5668(2) 0.45818(10) 0.3414(2) 0.0623(6) Uani 1 1 d . . .
H25 H 0.4814 0.4488 0.3259 0.075 Uiso 1 1 calc R . .
C26 C 0.6065(2) 0.51135(10) 0.3933(2) 0.0562(5) Uani 1 1 d . . .
H26 H 0.5485 0.5376 0.4134 0.067 Uiso 1 1 calc R . .
C27 C 0.6075(3) 0.36004(11) 0.2542(3) 0.0875(8) Uani 1 1 d . . .
H27A H 0.5265 0.3511 0.2718 0.131 Uiso 1 1 calc R . .
H27B H 0.6672 0.3307 0.2910 0.131 Uiso 1 1 calc R . .
H27C H 0.6005 0.3613 0.1632 0.131 Uiso 1 1 calc R . .


_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 O2 1.4261(16) . ?
S1 O3 1.4275(16) . ?
S1 N1 1.6701(17) . ?
S1 C21 1.765(2) . ?
Si1 C19 1.856(3) . ?
Si1 C18 1.858(3) . ?
Si1 C20 1.860(3) . ?
Si1 C15 1.912(2) . ?
N1 C13 1.434(2) . ?
N1 C1 1.472(2) . ?
O1 C16 1.413(4) . ?
O1 C15 1.432(3) . ?
O1 C16' 1.589(11) . ?
C1 C2 1.502(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.337(3) . ?
C2 C15 1.514(3) . ?
C3 C4 1.478(3) . ?
C3 C14 1.512(3) . ?
C4 C13 1.377(3) . ?
C4 C5 1.423(3) . ?
C5 C6 1.364(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.403(4) . ?
C6 H6 0.9300 . ?
C7 C12 1.411(3) . ?
C7 C8 1.428(3) . ?
C8 C9 1.355(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.384(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.361(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.416(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.422(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15 0.9800 . ?
C16 C17 1.466(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C16' C17' 1.480(16) . ?
C16' H16C 0.9700 . ?
C16' H16D 0.9700 . ?
C17' H17D 0.9600 . ?
C17' H17E 0.9600 . ?
C17' H17F 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.380(3) . ?
C21 C26 1.387(3) . ?
C22 C23 1.376(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.377(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.389(3) . ?
C24 C27 1.508(3) . ?
C25 C26 1.375(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

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
O2 S1 O3 119.68(10) . . ?
O2 S1 N1 106.26(9) . . ?
O3 S1 N1 106.07(9) . . ?
O2 S1 C21 108.84(10) . . ?
O3 S1 C21 106.45(10) . . ?
N1 S1 C21 109.23(9) . . ?
C19 Si1 C18 110.97(13) . . ?
C19 Si1 C20 109.88(13) . . ?
C18 Si1 C20 110.13(14) . . ?
C19 Si1 C15 109.35(12) . . ?
C18 Si1 C15 109.67(11) . . ?
C20 Si1 C15 106.76(11) . . ?
C13 N1 C1 112.14(16) . . ?
C13 N1 S1 114.22(12) . . ?
C1 N1 S1 118.16(13) . . ?
C16 O1 C15 122.6(3) . . ?
C16 O1 C16' 36.4(4) . . ?
C15 O1 C16' 94.0(5) . . ?
N1 C1 C2 112.93(16) . . ?
N1 C1 H1A 109.0 . . ?
C2 C1 H1A 109.0 . . ?
N1 C1 H1B 109.0 . . ?
C2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
C3 C2 C1 118.73(18) . . ?
C3 C2 C15 125.24(19) . . ?
C1 C2 C15 115.63(17) . . ?
C2 C3 C4 118.64(18) . . ?
C2 C3 C14 123.9(2) . . ?
C4 C3 C14 117.4(2) . . ?
C13 C4 C5 117.31(19) . . ?
C13 C4 C3 119.99(18) . . ?
C5 C4 C3 122.7(2) . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 122.1(2) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C6 C7 C12 118.6(2) . . ?
C6 C7 C8 122.5(2) . . ?
C12 C7 C8 118.9(3) . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 121.0(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 120.6(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C7 C12 C11 118.6(2) . . ?
C7 C12 C13 118.0(2) . . ?
C11 C12 C13 123.4(2) . . ?
C4 C13 C12 122.98(19) . . ?
C4 C13 N1 117.18(17) . . ?
C12 C13 N1 119.84(18) . . ?
C3 C14 H14A 109.5 . . ?
C3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 C2 113.95(18) . . ?
O1 C15 Si1 105.02(14) . . ?
C2 C15 Si1 113.78(14) . . ?
O1 C15 H15 107.9 . . ?
C2 C15 H15 107.9 . . ?
Si1 C15 H15 107.9 . . ?
O1 C16 C17 108.2(4) . . ?
O1 C16 H16A 110.1 . . ?
C17 C16 H16A 110.1 . . ?
O1 C16 H16B 110.1 . . ?
C17 C16 H16B 110.1 . . ?
H16A C16 H16B 108.4 . . ?
C17' C16' O1 104.5(9) . . ?
C17' C16' H16C 110.9 . . ?
O1 C16' H16C 110.9 . . ?
C17' C16' H16D 110.9 . . ?
O1 C16' H16D 110.9 . . ?
H16C C16' H16D 108.9 . . ?
C16' C17' H17D 109.5 . . ?
C16' C17' H17E 109.5 . . ?
H17D C17' H17E 109.5 . . ?
C16' C17' H17F 109.5 . . ?
H17D C17' H17F 109.5 . . ?
H17E C17' H17F 109.5 . . ?
Si1 C18 H18A 109.5 . . ?
Si1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
Si1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
Si1 C19 H19A 109.5 . . ?
Si1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
Si1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
Si1 C20 H20A 109.5 . . ?
Si1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
Si1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C26 120.1(2) . . ?
C22 C21 S1 119.85(16) . . ?
C26 C21 S1 119.97(16) . . ?
C23 C22 C21 119.2(2) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C22 C23 C24 121.9(2) . . ?
C22 C23 H23 119.0 . . ?
C24 C23 H23 119.0 . . ?
C23 C24 C25 117.9(2) . . ?
C23 C24 C27 121.1(2) . . ?
C25 C24 C27 121.0(2) . . ?
C26 C25 C24 121.3(2) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C25 C26 C21 119.5(2) . . ?
C25 C26 H26 120.3 . . ?
C21 C26 H26 120.3 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
O2 S1 N1 C13 168.99(13) . . . . ?
O3 S1 N1 C13 -62.65(15) . . . . ?
C21 S1 N1 C13 51.72(15) . . . . ?
O2 S1 N1 C1 33.78(16) . . . . ?
O3 S1 N1 C1 162.15(14) . . . . ?
C21 S1 N1 C1 -83.48(15) . . . . ?
C13 N1 C1 C2 -49.9(2) . . . . ?
S1 N1 C1 C2 86.22(19) . . . . ?
N1 C1 C2 C3 24.2(3) . . . . ?
N1 C1 C2 C15 -162.59(17) . . . . ?
C1 C2 C3 C4 10.3(3) . . . . ?
C15 C2 C3 C4 -162.13(18) . . . . ?
C1 C2 C3 C14 -172.9(2) . . . . ?
C15 C2 C3 C14 14.6(3) . . . . ?
C2 C3 C4 C13 -20.4(3) . . . . ?
C14 C3 C4 C13 162.7(2) . . . . ?
C2 C3 C4 C5 157.9(2) . . . . ?
C14 C3 C4 C5 -19.0(3) . . . . ?
C13 C4 C5 C6 2.1(3) . . . . ?
C3 C4 C5 C6 -176.3(2) . . . . ?
C4 C5 C6 C7 1.3(3) . . . . ?
C5 C6 C7 C12 -1.7(3) . . . . ?
C5 C6 C7 C8 176.9(2) . . . . ?
C6 C7 C8 C9 -177.2(2) . . . . ?
C12 C7 C8 C9 1.4(4) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
C8 C9 C10 C11 -1.6(4) . . . . ?
C9 C10 C11 C12 1.5(4) . . . . ?
C6 C7 C12 C11 177.2(2) . . . . ?
C8 C7 C12 C11 -1.5(3) . . . . ?
C6 C7 C12 C13 -1.3(3) . . . . ?
C8 C7 C12 C13 -179.93(19) . . . . ?
C10 C11 C12 C7 0.0(3) . . . . ?
C10 C11 C12 C13 178.4(2) . . . . ?
C5 C4 C13 C12 -5.2(3) . . . . ?
C3 C4 C13 C12 173.15(17) . . . . ?
C5 C4 C13 N1 174.56(17) . . . . ?
C3 C4 C13 N1 -7.1(3) . . . . ?
C7 C12 C13 C4 4.9(3) . . . . ?
C11 C12 C13 C4 -173.53(19) . . . . ?
C7 C12 C13 N1 -174.91(17) . . . . ?
C11 C12 C13 N1 6.7(3) . . . . ?
C1 N1 C13 C4 41.6(2) . . . . ?
S1 N1 C13 C4 -96.26(18) . . . . ?
C1 N1 C13 C12 -138.57(17) . . . . ?
S1 N1 C13 C12 83.54(19) . . . . ?
C16 O1 C15 C2 68.1(3) . . . . ?
C16' O1 C15 C2 92.2(5) . . . . ?
C16 O1 C15 Si1 -166.7(2) . . . . ?
C16' O1 C15 Si1 -142.6(5) . . . . ?
C3 C2 C15 O1 -150.5(2) . . . . ?
C1 C2 C15 O1 36.8(2) . . . . ?
C3 C2 C15 Si1 89.1(2) . . . . ?
C1 C2 C15 Si1 -83.5(2) . . . . ?
C19 Si1 C15 O1 -176.77(14) . . . . ?
C18 Si1 C15 O1 -54.88(17) . . . . ?
C20 Si1 C15 O1 64.41(17) . . . . ?
C19 Si1 C15 C2 -51.49(19) . . . . ?
C18 Si1 C15 C2 70.40(19) . . . . ?
C20 Si1 C15 C2 -170.31(16) . . . . ?
C15 O1 C16 C17 79.5(6) . . . . ?
C16' O1 C16 C17 36.2(8) . . . . ?
C16 O1 C16' C17' -44.5(8) . . . . ?
C15 O1 C16' C17' 170.9(9) . . . . ?
O2 S1 C21 C22 -10.2(2) . . . . ?
O3 S1 C21 C22 -140.49(17) . . . . ?
N1 S1 C21 C22 105.39(17) . . . . ?
O2 S1 C21 C26 167.54(16) . . . . ?
O3 S1 C21 C26 37.29(19) . . . . ?
N1 S1 C21 C26 -76.84(18) . . . . ?
C26 C21 C22 C23 1.2(3) . . . . ?
S1 C21 C22 C23 178.94(16) . . . . ?
C21 C22 C23 C24 0.7(3) . . . . ?
C22 C23 C24 C25 -2.0(3) . . . . ?
C22 C23 C24 C27 179.1(2) . . . . ?
C23 C24 C25 C26 1.3(3) . . . . ?
C27 C24 C25 C26 -179.8(2) . . . . ?
C24 C25 C26 C21 0.5(3) . . . . ?
C22 C21 C26 C25 -1.8(3) . . . . ?
S1 C21 C26 C25 -179.55(16) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_cd214703
_database_code_depnum_ccdc_archive 'CCDC 1038047'
_audit_update_record             
;
2014-12-08 deposited with the CCDC.
2015-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        cd214703
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H28 Cl N O3 S Si'
_chemical_formula_weight         498.09

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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   32.673(2)
_cell_length_b                   12.2122(8)
_cell_length_c                   12.9554(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.633(2)
_cell_angle_gamma                90
_cell_volume                     5163.9(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4555
_cell_measurement_theta_min      4.715
_cell_measurement_theta_max      55.215

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             2096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.112
_exptl_absorpt_coefficient_mu    0.303
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4563
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15390
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.780
_diffrn_reflns_theta_max         25.992
_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             5066
_reflns_number_gt                4155
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0641P)²+3.1071P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5066
_refine_ls_number_parameters     306
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1241
_refine_ls_wR_factor_gt          0.1166
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.017
_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 0.35724(2) 0.49057(4) 0.13602(4) 0.04396(16) Uani 1 1 d . . . . .
Si1 Si 0.34689(2) 1.00486(5) 0.09670(5) 0.04674(17) Uani 1 1 d . . . . .
Cl1 Cl 0.46941(2) 0.90214(6) 0.36927(6) 0.0809(2) Uani 1 1 d . . . . .
N1 N 0.39030(5) 0.57628(12) 0.08515(12) 0.0381(4) Uani 1 1 d . . . . .
O1 O 0.37376(5) 0.75220(12) -0.14640(11) 0.0461(4) Uani 1 1 d . . . . .
O2 O 0.34089(5) 0.42651(12) 0.05212(13) 0.0592(4) Uani 1 1 d . . . . .
O3 O 0.37764(5) 0.43706(12) 0.22186(12) 0.0574(4) Uani 1 1 d . . . . .
C1 C 0.41039(6) 0.65477(15) 0.15270(14) 0.0366(4) Uani 1 1 d . . . . .
C2 C 0.43303(6) 0.62073(18) 0.24049(16) 0.0478(5) Uani 1 1 d . . . . .
H2 H 0.4362 0.5463 0.2539 0.057 Uiso 1 1 calc R U . . .
C3 C 0.45087(7) 0.6962(2) 0.30776(17) 0.0563(6) Uani 1 1 d . . . . .
H3 H 0.4651 0.6731 0.3676 0.068 Uiso 1 1 calc R U . . .
C4 C 0.44733(6) 0.80600(19) 0.28535(17) 0.0513(5) Uani 1 1 d . . . . .
C5 C 0.42754(6) 0.84079(17) 0.19507(16) 0.0453(5) Uani 1 1 d . . . . .
H5 H 0.4273 0.9149 0.1786 0.054 Uiso 1 1 calc R U . . .
C6 C 0.40798(5) 0.76658(15) 0.12846(14) 0.0358(4) Uani 1 1 d . . . . .
C7 C 0.38844(6) 0.80249(14) 0.02958(14) 0.0354(4) Uani 1 1 d . . . . .
C8 C 0.39582(6) 0.71906(14) -0.05461(14) 0.0361(4) Uani 1 1 d . . . . .
C9 C 0.37588(6) 0.61295(15) -0.01963(15) 0.0399(4) Uani 1 1 d . . . . .
H9A H 0.3464 0.6233 -0.0204 0.048 Uiso 1 1 calc R U . . .
H9B H 0.3814 0.5556 -0.0689 0.048 Uiso 1 1 calc R U . . .
C10 C 0.44118(6) 0.70852(15) -0.07481(14) 0.0388(4) Uani 1 1 d . . . . .
C11 C 0.46274(8) 0.80229(19) -0.0970(2) 0.0626(6) Uani 1 1 d . . . . .
H11 H 0.4496 0.8699 -0.0959 0.075 Uiso 1 1 calc R U . . .
C12 C 0.50335(8) 0.7971(2) -0.1206(2) 0.0778(8) Uani 1 1 d . . . . .
H12 H 0.5175 0.8608 -0.1357 0.093 Uiso 1 1 calc R U . . .
C13 C 0.52309(8) 0.6974(3) -0.1220(2) 0.0698(7) Uani 1 1 d . . . . .
H13 H 0.5506 0.6939 -0.1372 0.084 Uiso 1 1 calc R U . . .
C14 C 0.50223(7) 0.6044(2) -0.10102(19) 0.0612(6) Uani 1 1 d . . . . .
H14 H 0.5155 0.5371 -0.1029 0.073 Uiso 1 1 calc R U . . .
C15 C 0.46141(7) 0.60916(18) -0.07689(17) 0.0502(5) Uani 1 1 d . . . . .
H15 H 0.4475 0.5450 -0.0620 0.060 Uiso 1 1 calc R U . . .
C16 C 0.36686(6) 0.89434(15) 0.01316(15) 0.0431(5) Uani 1 1 d . . . . .
H16 H 0.3602 0.9060 -0.0566 0.052 Uiso 1 1 calc R U . . .
C17 C 0.33973(11) 0.9658(3) 0.2330(2) 0.0903(10) Uani 1 1 d . . . . .
H17A H 0.3653 0.9727 0.2720 0.135 Uiso 1 1 calc R U . . .
H17B H 0.3304 0.8913 0.2358 0.135 Uiso 1 1 calc R U . . .
H17C H 0.3197 1.0131 0.2619 0.135 Uiso 1 1 calc R U . . .
C18 C 0.37993(11) 1.1268(2) 0.0920(3) 0.1043(12) Uani 1 1 d . . . . .
H18A H 0.4052 1.1132 0.1308 0.156 Uiso 1 1 calc R U . . .
H18B H 0.3662 1.1882 0.1213 0.156 Uiso 1 1 calc R U . . .
H18C H 0.3856 1.1426 0.0215 0.156 Uiso 1 1 calc R U . . .
C19 C 0.29545(10) 1.0365(4) 0.0374(3) 0.1253(17) Uani 1 1 d . . . . .
H19A H 0.2841 1.0983 0.0718 0.188 Uiso 1 1 calc R U . . .
H19B H 0.2778 0.9743 0.0441 0.188 Uiso 1 1 calc R U . . .
H19C H 0.2978 1.0532 -0.0345 0.188 Uiso 1 1 calc R U . . .
C20 C 0.31855(6) 0.57444(16) 0.18339(17) 0.0466(5) Uani 1 1 d . . . . .
C21 C 0.32248(7) 0.6167(2) 0.28191(19) 0.0577(6) Uani 1 1 d . . . . .
H21 H 0.3447 0.5975 0.3256 0.069 Uiso 1 1 calc R U . . .
C22 C 0.29288(8) 0.6880(2) 0.3148(2) 0.0688(7) Uani 1 1 d . . . . .
H22 H 0.2954 0.7165 0.3814 0.083 Uiso 1 1 calc R U . . .
C23 C 0.25975(7) 0.7178(2) 0.2512(3) 0.0686(7) Uani 1 1 d . . . . .
C24 C 0.25621(7) 0.6725(2) 0.1541(3) 0.0736(8) Uani 1 1 d . . . . .
H24 H 0.2337 0.6906 0.1109 0.088 Uiso 1 1 calc R U . . .
C25 C 0.28512(7) 0.6011(2) 0.1189(2) 0.0607(6) Uani 1 1 d . . . . .
H25 H 0.2822 0.5712 0.0529 0.073 Uiso 1 1 calc R U . . .
C26 C 0.22861(9) 0.7992(3) 0.2871(3) 0.1052(12) Uani 1 1 d . . . . .
H26A H 0.2348 0.8174 0.3582 0.158 Uiso 1 1 calc R U . . .
H26B H 0.2017 0.7677 0.2801 0.158 Uiso 1 1 calc R U . . .
H26C H 0.2296 0.8643 0.2457 0.158 Uiso 1 1 calc R U . . .
H1 H 0.3755(8) 0.707(2) -0.191(2) 0.067(8) Uiso 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4233(16) . ?
S1 O3 1.4283(16) . ?
S1 N1 1.6619(16) . ?
S1 C20 1.759(2) . ?
Si1 C18 1.842(3) . ?
Si1 C17 1.855(3) . ?
Si1 C19 1.856(3) . ?
Si1 C16 1.866(2) . ?
Cl1 C4 1.735(2) . ?
N1 C1 1.436(2) . ?
N1 C9 1.485(2) . ?
O1 C8 1.421(2) . ?
O1 H1 0.80(3) . ?
C1 C2 1.392(3) . ?
C1 C6 1.402(3) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(3) . ?
C5 C6 1.387(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.472(2) . ?
C7 C16 1.337(3) . ?
C7 C8 1.520(2) . ?
C8 C10 1.522(3) . ?
C8 C9 1.529(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.381(3) . ?
C10 C15 1.383(3) . ?
C11 C12 1.377(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.359(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.377(3) . ?
C20 C25 1.383(3) . ?
C21 C22 1.383(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.379(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.375(4) . ?
C23 C26 1.511(4) . ?
C24 C25 1.379(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

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
O2 S1 O3 119.25(10) . . ?
O2 S1 N1 105.74(9) . . ?
O3 S1 N1 107.96(9) . . ?
O2 S1 C20 109.62(10) . . ?
O3 S1 C20 108.18(10) . . ?
N1 S1 C20 105.20(9) . . ?
C18 Si1 C17 109.82(18) . . ?
C18 Si1 C19 109.8(2) . . ?
C17 Si1 C19 107.24(19) . . ?
C18 Si1 C16 110.15(12) . . ?
C17 Si1 C16 115.40(12) . . ?
C19 Si1 C16 104.15(12) . . ?
C1 N1 C9 118.20(14) . . ?
C1 N1 S1 117.77(12) . . ?
C9 N1 S1 111.57(12) . . ?
C8 O1 H1 110.8(19) . . ?
C2 C1 C6 119.75(18) . . ?
C2 C1 N1 120.63(17) . . ?
C6 C1 N1 119.60(16) . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 119.3(2) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 Cl1 119.93(17) . . ?
C5 C4 Cl1 119.27(17) . . ?
C4 C5 C6 120.78(19) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 118.51(17) . . ?
C5 C6 C7 121.06(17) . . ?
C1 C6 C7 120.18(16) . . ?
C16 C7 C6 126.38(17) . . ?
C16 C7 C8 123.24(17) . . ?
C6 C7 C8 110.37(15) . . ?
O1 C8 C7 108.58(14) . . ?
O1 C8 C10 109.92(15) . . ?
C7 C8 C10 111.58(15) . . ?
O1 C8 C9 106.43(15) . . ?
C7 C8 C9 105.76(15) . . ?
C10 C8 C9 114.26(15) . . ?
N1 C9 C8 113.89(15) . . ?
N1 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
N1 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C15 118.3(2) . . ?
C11 C10 C8 118.38(18) . . ?
C15 C10 C8 123.21(18) . . ?
C12 C11 C10 120.9(2) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 120.0(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C10 C15 C14 120.5(2) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C7 C16 Si1 135.27(16) . . ?
C7 C16 H16 112.4 . . ?
Si1 C16 H16 112.4 . . ?
Si1 C17 H17A 109.5 . . ?
Si1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
Si1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Si1 C18 H18A 109.5 . . ?
Si1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
Si1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
Si1 C19 H19A 109.5 . . ?
Si1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
Si1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C25 120.6(2) . . ?
C21 C20 S1 120.23(17) . . ?
C25 C20 S1 119.09(18) . . ?
C20 C21 C22 119.0(2) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C23 C22 C21 121.5(3) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C24 C23 C22 118.2(2) . . ?
C24 C23 C26 121.1(3) . . ?
C22 C23 C26 120.7(3) . . ?
C23 C24 C25 121.8(3) . . ?
C23 C24 H24 119.1 . . ?
C25 C24 H24 119.1 . . ?
C24 C25 C20 118.9(2) . . ?
C24 C25 H25 120.6 . . ?
C20 C25 H25 120.6 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
O2 S1 N1 C1 177.48(13) . . . . ?
O3 S1 N1 C1 -53.85(15) . . . . ?
C20 S1 N1 C1 61.49(16) . . . . ?
O2 S1 N1 C9 36.00(15) . . . . ?
O3 S1 N1 C9 164.67(13) . . . . ?
C20 S1 N1 C9 -79.99(15) . . . . ?
C9 N1 C1 C2 -164.47(17) . . . . ?
S1 N1 C1 C2 56.6(2) . . . . ?
C9 N1 C1 C6 13.9(2) . . . . ?
S1 N1 C1 C6 -124.97(16) . . . . ?
C6 C1 C2 C3 4.4(3) . . . . ?
N1 C1 C2 C3 -177.20(19) . . . . ?
C1 C2 C3 C4 -2.3(3) . . . . ?
C2 C3 C4 C5 -2.4(3) . . . . ?
C2 C3 C4 Cl1 179.77(17) . . . . ?
C3 C4 C5 C6 5.0(3) . . . . ?
Cl1 C4 C5 C6 -177.11(16) . . . . ?
C4 C5 C6 C1 -2.9(3) . . . . ?
C4 C5 C6 C7 -177.12(18) . . . . ?
C2 C1 C6 C5 -1.8(3) . . . . ?
N1 C1 C6 C5 179.81(16) . . . . ?
C2 C1 C6 C7 172.52(17) . . . . ?
N1 C1 C6 C7 -5.9(3) . . . . ?
C5 C6 C7 C16 -39.7(3) . . . . ?
C1 C6 C7 C16 146.2(2) . . . . ?
C5 C6 C7 C8 140.67(18) . . . . ?
C1 C6 C7 C8 -33.5(2) . . . . ?
C16 C7 C8 O1 -4.4(3) . . . . ?
C6 C7 C8 O1 175.32(15) . . . . ?
C16 C7 C8 C10 117.0(2) . . . . ?
C6 C7 C8 C10 -63.38(19) . . . . ?
C16 C7 C8 C9 -118.2(2) . . . . ?
C6 C7 C8 C9 61.43(19) . . . . ?
C1 N1 C9 C8 18.2(2) . . . . ?
S1 N1 C9 C8 159.47(13) . . . . ?
O1 C8 C9 N1 -169.97(15) . . . . ?
C7 C8 C9 N1 -54.6(2) . . . . ?
C10 C8 C9 N1 68.5(2) . . . . ?
O1 C8 C10 C11 66.6(2) . . . . ?
C7 C8 C10 C11 -53.9(2) . . . . ?
C9 C8 C10 C11 -173.80(19) . . . . ?
O1 C8 C10 C15 -110.2(2) . . . . ?
C7 C8 C10 C15 129.3(2) . . . . ?
C9 C8 C10 C15 9.4(3) . . . . ?
C15 C10 C11 C12 0.1(4) . . . . ?
C8 C10 C11 C12 -176.9(2) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C11 C12 C13 C14 0.7(4) . . . . ?
C12 C13 C14 C15 -0.9(4) . . . . ?
C11 C10 C15 C14 -0.2(3) . . . . ?
C8 C10 C15 C14 176.61(19) . . . . ?
C13 C14 C15 C10 0.7(4) . . . . ?
C6 C7 C16 Si1 -7.8(3) . . . . ?
C8 C7 C16 Si1 171.83(16) . . . . ?
C18 Si1 C16 C7 101.6(3) . . . . ?
C17 Si1 C16 C7 -23.4(3) . . . . ?
C19 Si1 C16 C7 -140.7(3) . . . . ?
O2 S1 C20 C21 159.12(17) . . . . ?
O3 S1 C20 C21 27.6(2) . . . . ?
N1 S1 C20 C21 -87.59(19) . . . . ?
O2 S1 C20 C25 -23.7(2) . . . . ?
O3 S1 C20 C25 -155.19(17) . . . . ?
N1 S1 C20 C25 89.62(19) . . . . ?
C25 C20 C21 C22 -1.3(3) . . . . ?
S1 C20 C21 C22 175.90(18) . . . . ?
C20 C21 C22 C23 -0.2(4) . . . . ?
C21 C22 C23 C24 1.5(4) . . . . ?
C21 C22 C23 C26 -177.6(3) . . . . ?
C22 C23 C24 C25 -1.4(4) . . . . ?
C26 C23 C24 C25 177.7(3) . . . . ?
C23 C24 C25 C20 0.0(4) . . . . ?
C21 C20 C25 C24 1.4(4) . . . . ?
S1 C20 C25 C24 -175.80(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O3 0.80(3) 2.09(3) 2.879(2) 166(3) 6_565
C2 H2 O3 0.93 2.35 2.885(3) 116.1 .
O1 H1 O3 0.80(3) 2.09(3) 2.879(2) 166(3) 6_565
C2 H2 O3 0.93 2.35 2.885(3) 116.1 .
C2 H2 O3 0.93 2.35 2.885(3) 116.1 .
O1 H1 O3 0.80(3) 2.09(3) 2.879(2) 166(3) 6_565

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-4

