# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

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

data_s9
_database_code_depnum_ccdc_archive 'CCDC 1428620'
_audit_update_record             
;
2016-04-13 deposited with the CCDC.
2016-05-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H25 N O5 S Si'
_chemical_formula_sum            'C17 H25 N O5 S Si'
_chemical_formula_weight         383.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   8.3421(6)
_cell_length_b                   13.3327(10)
_cell_length_c                   16.7969(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1868.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    33751
_cell_measurement_theta_min      2.726
_cell_measurement_theta_max      28.330

_exptl_crystal_description       plates
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.264
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_process_details   'SADABS (Sheldrick 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33751
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.726
_diffrn_reflns_theta_max         28.330
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4651
_reflns_number_gt                4370
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'APEX2 (Bruker, 2013)'
_computing_structure_solution    'SHELXT-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    Diamond
_computing_publication_material  ?

_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)+(0.0577P)²+0.6341P] 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_abs_structure_details 
;
 Flack x determined using 1826 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.020(16)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4651
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.1007
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.44329(9) 0.23592(5) 0.67083(4) 0.02801(16) Uani 1 1 d . . . . .
S1 S 0.10959(9) 0.50959(5) 0.53329(4) 0.03832(17) Uani 1 1 d . . . . .
O1 O 0.0335(3) 1.00563(16) 0.57450(13) 0.0434(5) Uani 1 1 d . . . . .
O2 O -0.0995(3) 0.54801(19) 0.64548(17) 0.0633(7) Uani 1 1 d . . . . .
C1 C 0.1332(4) 1.0528(2) 0.51664(19) 0.0434(7) Uani 1 1 d . . . . .
H1A H 0.1228 1.1258 0.5212 0.065 Uiso 1 1 calc R U . . .
H1B H 0.1002 1.0316 0.4632 0.065 Uiso 1 1 calc R U . . .
H1C H 0.2450 1.0335 0.5257 0.065 Uiso 1 1 calc R U . . .
C2 C 0.0327(3) 0.9039(2) 0.57686(17) 0.0337(5) Uani 1 1 d . . . . .
C3 C -0.0606(4) 0.8601(2) 0.63586(19) 0.0435(7) Uani 1 1 d . . . . .
H3 H -0.1179 0.9015 0.6720 0.052 Uiso 1 1 calc R U . . .
C4 C -0.0713(3) 0.7571(2) 0.64264(18) 0.0408(6) Uani 1 1 d . . . . .
H4 H -0.1349 0.7281 0.6835 0.049 Uiso 1 1 calc R U . . .
C5 C 0.0116(3) 0.6952(2) 0.58932(15) 0.0325(5) Uani 1 1 d . . . . .
C6 C 0.1072(3) 0.7391(2) 0.53187(15) 0.0333(5) Uani 1 1 d . . . . .
H6 H 0.1655 0.6975 0.4962 0.040 Uiso 1 1 calc R U . . .
C7 C 0.1202(3) 0.8425(2) 0.52496(15) 0.0334(5) Uani 1 1 d . . . . .
H7 H 0.1876 0.8713 0.4855 0.040 Uiso 1 1 calc R U . . .
C8 C -0.0084(3) 0.5847(2) 0.59808(17) 0.0356(6) Uani 1 1 d . . . . .
C9 C 0.0456(4) 0.3852(2) 0.56412(18) 0.0372(6) Uani 1 1 d . . . . .
H9A H -0.0659 0.3893 0.5839 0.045 Uiso 1 1 calc R U . . .
H9B H 0.0459 0.3405 0.5171 0.045 Uiso 1 1 calc R U . . .
C10 C 0.1504(3) 0.3385(2) 0.62884(16) 0.0338(5) Uani 1 1 d . . . . .
H10A H 0.1508 0.3834 0.6758 0.041 Uiso 1 1 calc R U . . .
H10B H 0.1022 0.2739 0.6454 0.041 Uiso 1 1 calc R U . . .
C11 C 0.3235(3) 0.3198(2) 0.60309(15) 0.0306(5) Uani 1 1 d . . . . .
H11A H 0.3789 0.3853 0.5991 0.037 Uiso 1 1 calc R U . . .
H11B H 0.3224 0.2897 0.5492 0.037 Uiso 1 1 calc R U . . .
N1 N 0.5833(3) 0.13622(19) 0.74702(15) 0.0393(5) Uani 1 1 d . . . . .
C21 C 0.7587(11) 0.1481(9) 0.7122(6) 0.063(2) Uani 0.5 1 d . . P A 1
H21A H 0.8229 0.1916 0.7477 0.075 Uiso 0.5 1 calc R U P A 1
H21B H 0.8112 0.0816 0.7097 0.075 Uiso 0.5 1 calc R U P A 1
C21' C 0.7078(8) 0.1010(5) 0.7005(4) 0.0365(14) Uani 0.5 1 d . . P A 2
H21C H 0.6740 0.0403 0.6709 0.044 Uiso 0.5 1 calc R U P A 2
H21D H 0.8010 0.0834 0.7342 0.044 Uiso 0.5 1 calc R U P A 2
C22 C 0.7532(4) 0.1873(3) 0.6409(3) 0.0609(10) Uani 1 1 d . . . . .
H22A H 0.7734 0.1329 0.6021 0.073 Uiso 0.5 1 calc R U P A 1
H22B H 0.8433 0.2354 0.6364 0.073 Uiso 0.5 1 calc R U P A 1
H22C H 0.8273 0.2351 0.6671 0.073 Uiso 0.5 1 calc R U P A 2
H22D H 0.8079 0.1589 0.5937 0.073 Uiso 0.5 1 calc R U P A 2
O21 O 0.6119(2) 0.23772(18) 0.61719(12) 0.0427(5) Uani 1 1 d . . . . .
C31 C 0.5392(13) 0.0338(7) 0.7230(8) 0.090(4) Uani 0.5 1 d . . P A 1
H31A H 0.5541 -0.0139 0.7675 0.108 Uiso 0.5 1 calc R U P A 1
H31B H 0.6043 0.0113 0.6770 0.108 Uiso 0.5 1 calc R U P A 1
C31' C 0.4607(6) 0.0560(3) 0.7729(3) 0.0237(9) Uani 0.5 1 d . . P A 2
H31C H 0.5149 -0.0075 0.7875 0.028 Uiso 0.5 1 calc R U P A 2
H31D H 0.3960 0.0795 0.8186 0.028 Uiso 0.5 1 calc R U P A 2
C32 C 0.3584(4) 0.0426(2) 0.6998(2) 0.0430(7) Uani 1 1 d . . . . .
H32A H 0.3314 -0.0108 0.6611 0.052 Uiso 0.5 1 calc R U P A 1
H32B H 0.2916 0.0324 0.7478 0.052 Uiso 0.5 1 calc R U P A 1
H32C H 0.4160 0.0008 0.6604 0.052 Uiso 0.5 1 calc R U P A 2
H32D H 0.2577 0.0079 0.7142 0.052 Uiso 0.5 1 calc R U P A 2
O31 O 0.3227(3) 0.13727(15) 0.66605(15) 0.0495(6) Uani 1 1 d . . . . .
C41 C 0.6090(6) 0.1927(4) 0.8191(2) 0.0788(15) Uani 1 1 d . . . . .
H41A H 0.7195 0.2198 0.8191 0.095 Uiso 1 1 calc R U . . .
H41B H 0.5982 0.1475 0.8655 0.095 Uiso 1 1 calc R U . . .
C42 C 0.4969(5) 0.2745(2) 0.82701(19) 0.0536(9) Uani 1 1 d . . . . .
H42A H 0.4066 0.2530 0.8613 0.064 Uiso 1 1 calc R U . . .
H42B H 0.5507 0.3316 0.8535 0.064 Uiso 1 1 calc R U . . .
O41 O 0.4366(3) 0.30609(15) 0.75310(11) 0.0359(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
Si1 O31 1.658(2) . ?
Si1 O41 1.670(2) . ?
Si1 O21 1.670(2) . ?
Si1 C11 1.883(3) . ?
Si1 N1 2.184(2) . ?
S1 C8 1.777(3) . ?
S1 C9 1.817(3) . ?
O1 C2 1.357(3) . ?
O1 C1 1.425(4) . ?
O2 C8 1.205(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.389(4) . ?
C2 C7 1.401(4) . ?
C3 C4 1.381(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.400(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(4) . ?
C5 C8 1.490(4) . ?
C6 C7 1.387(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C9 C10 1.528(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.528(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N1 C21' 1.382(7) . ?
N1 C41 1.441(5) . ?
N1 C31 1.471(9) . ?
N1 C31' 1.542(5) . ?
N1 C21 1.583(10) . ?
C21 C22 1.307(10) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21' C22 1.572(8) . ?
C21' H21C 0.9900 . ?
C21' H21D 0.9900 . ?
C22 O21 1.415(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 H22C 0.9900 . ?
C22 H22D 0.9900 . ?
C31 C32 1.562(10) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31' C32 1.505(6) . ?
C31' H31C 0.9900 . ?
C31' H31D 0.9900 . ?
C32 O31 1.415(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 H32C 0.9900 . ?
C32 H32D 0.9900 . ?
C41 C42 1.442(5) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 O41 1.404(4) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?

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
O31 Si1 O41 117.67(13) . . ?
O31 Si1 O21 119.74(14) . . ?
O41 Si1 O21 117.81(12) . . ?
O31 Si1 C11 96.89(11) . . ?
O41 Si1 C11 98.61(11) . . ?
O21 Si1 C11 96.45(11) . . ?
O31 Si1 N1 82.53(10) . . ?
O41 Si1 N1 82.76(10) . . ?
O21 Si1 N1 82.79(10) . . ?
C11 Si1 N1 178.63(12) . . ?
C8 S1 C9 100.20(14) . . ?
C2 O1 C1 117.6(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 116.4(2) . . ?
O1 C2 C7 124.3(3) . . ?
C3 C2 C7 119.3(3) . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 118.8(3) . . ?
C6 C5 C8 123.5(2) . . ?
C4 C5 C8 117.6(2) . . ?
C5 C6 C7 121.6(3) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C2 119.2(3) . . ?
C6 C7 H7 120.4 . . ?
C2 C7 H7 120.4 . . ?
O2 C8 C5 122.5(3) . . ?
O2 C8 S1 121.7(2) . . ?
C5 C8 S1 115.8(2) . . ?
C10 C9 S1 114.0(2) . . ?
C10 C9 H9A 108.8 . . ?
S1 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
S1 C9 H9B 108.8 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C9 113.9(2) . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 Si1 115.31(17) . . ?
C10 C11 H11A 108.4 . . ?
Si1 C11 H11A 108.4 . . ?
C10 C11 H11B 108.4 . . ?
Si1 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C21' N1 C41 122.7(4) . . ?
C41 N1 C31 138.9(6) . . ?
C21' N1 C31' 114.9(4) . . ?
C41 N1 C31' 103.0(3) . . ?
C41 N1 C21 96.9(5) . . ?
C31 N1 C21 102.8(7) . . ?
C21' N1 Si1 106.1(3) . . ?
C41 N1 Si1 104.7(2) . . ?
C31 N1 Si1 105.7(4) . . ?
C31' N1 Si1 103.4(2) . . ?
C21 N1 Si1 102.5(3) . . ?
C22 C21 N1 110.3(6) . . ?
C22 C21 H21A 109.6 . . ?
N1 C21 H21A 109.6 . . ?
C22 C21 H21B 109.6 . . ?
N1 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
N1 C21' C22 107.0(4) . . ?
N1 C21' H21C 110.3 . . ?
C22 C21' H21C 110.3 . . ?
N1 C21' H21D 110.3 . . ?
C22 C21' H21D 110.3 . . ?
H21C C21' H21D 108.6 . . ?
C21 C22 O21 118.5(5) . . ?
O21 C22 C21' 109.0(3) . . ?
C21 C22 H22A 107.7 . . ?
O21 C22 H22A 107.7 . . ?
C21 C22 H22B 107.7 . . ?
O21 C22 H22B 107.7 . . ?
H22A C22 H22B 107.1 . . ?
O21 C22 H22C 109.9 . . ?
C21' C22 H22C 109.9 . . ?
O21 C22 H22D 109.9 . . ?
C21' C22 H22D 109.9 . . ?
H22C C22 H22D 108.3 . . ?
C22 O21 Si1 122.9(2) . . ?
N1 C31 C32 103.9(6) . . ?
N1 C31 H31A 111.0 . . ?
C32 C31 H31A 111.0 . . ?
N1 C31 H31B 111.0 . . ?
C32 C31 H31B 111.0 . . ?
H31A C31 H31B 109.0 . . ?
C32 C31' N1 103.2(3) . . ?
C32 C31' H31C 111.1 . . ?
N1 C31' H31C 111.1 . . ?
C32 C31' H31D 111.1 . . ?
N1 C31' H31D 111.1 . . ?
H31C C31' H31D 109.1 . . ?
O31 C32 C31' 109.9(3) . . ?
O31 C32 C31 111.7(4) . . ?
O31 C32 H32A 109.3 . . ?
C31 C32 H32A 109.3 . . ?
O31 C32 H32B 109.3 . . ?
C31 C32 H32B 109.3 . . ?
H32A C32 H32B 107.9 . . ?
O31 C32 H32C 109.7 . . ?
C31' C32 H32C 109.7 . . ?
O31 C32 H32D 109.7 . . ?
C31' C32 H32D 109.7 . . ?
H32C C32 H32D 108.2 . . ?
C32 O31 Si1 124.10(19) . . ?
N1 C41 C42 112.1(3) . . ?
N1 C41 H41A 109.2 . . ?
C42 C41 H41A 109.2 . . ?
N1 C41 H41B 109.2 . . ?
C42 C41 H41B 109.2 . . ?
H41A C41 H41B 107.9 . . ?
O41 C42 C41 112.2(3) . . ?
O41 C42 H42A 109.2 . . ?
C41 C42 H42A 109.2 . . ?
O41 C42 H42B 109.2 . . ?
C41 C42 H42B 109.2 . . ?
H42A C42 H42B 107.9 . . ?
C42 O41 Si1 123.47(19) . . ?

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
C1 O1 C2 C3 177.5(3) . . . . ?
C1 O1 C2 C7 -1.6(4) . . . . ?
O1 C2 C3 C4 179.1(3) . . . . ?
C7 C2 C3 C4 -1.7(5) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C3 C4 C5 C6 1.9(4) . . . . ?
C3 C4 C5 C8 -178.2(3) . . . . ?
C4 C5 C6 C7 -1.3(4) . . . . ?
C8 C5 C6 C7 178.8(3) . . . . ?
C5 C6 C7 C2 -0.8(4) . . . . ?
O1 C2 C7 C6 -178.6(3) . . . . ?
C3 C2 C7 C6 2.3(4) . . . . ?
C6 C5 C8 O2 -175.5(3) . . . . ?
C4 C5 C8 O2 4.6(5) . . . . ?
C6 C5 C8 S1 3.9(4) . . . . ?
C4 C5 C8 S1 -176.0(2) . . . . ?
C9 S1 C8 O2 -0.1(3) . . . . ?
C9 S1 C8 C5 -179.5(2) . . . . ?
C8 S1 C9 C10 -92.5(2) . . . . ?
S1 C9 C10 C11 -63.4(3) . . . . ?
C9 C10 C11 Si1 -166.26(19) . . . . ?
O31 Si1 C11 C10 57.6(2) . . . . ?
O41 Si1 C11 C10 -61.9(2) . . . . ?
O21 Si1 C11 C10 178.7(2) . . . . ?
C21' N1 C21 C22 83.3(11) . . . . ?
C41 N1 C21 C22 -124.1(8) . . . . ?
C31 N1 C21 C22 92.2(9) . . . . ?
C31' N1 C21 C22 114.5(7) . . . . ?
Si1 N1 C21 C22 -17.4(9) . . . . ?
C41 N1 C21' C22 -87.0(5) . . . . ?
C31 N1 C21' C22 135.0(6) . . . . ?
C31' N1 C21' C22 146.6(4) . . . . ?
C21 N1 C21' C22 -54.1(9) . . . . ?
Si1 N1 C21' C22 33.0(5) . . . . ?
N1 C21 C22 O21 18.0(11) . . . . ?
N1 C21 C22 C21' -60.4(9) . . . . ?
N1 C21' C22 C21 77.6(10) . . . . ?
N1 C21' C22 O21 -36.8(6) . . . . ?
C21 C22 O21 Si1 -8.6(8) . . . . ?
C21' C22 O21 Si1 22.4(5) . . . . ?
O31 Si1 O21 C22 -80.0(3) . . . . ?
O41 Si1 O21 C22 75.0(3) . . . . ?
C11 Si1 O21 C22 178.2(3) . . . . ?
N1 Si1 O21 C22 -2.9(3) . . . . ?
C21' N1 C31 C32 -136.8(8) . . . . ?
C41 N1 C31 C32 102.0(7) . . . . ?
C31' N1 C31 C32 58.8(6) . . . . ?
C21 N1 C31 C32 -141.3(7) . . . . ?
Si1 N1 C31 C32 -34.2(8) . . . . ?
C21' N1 C31' C32 -78.8(4) . . . . ?
C41 N1 C31' C32 145.2(3) . . . . ?
C31 N1 C31' C32 -62.3(6) . . . . ?
C21 N1 C31' C32 -95.2(7) . . . . ?
Si1 N1 C31' C32 36.4(3) . . . . ?
N1 C31' C32 O31 -43.0(4) . . . . ?
N1 C31' C32 C31 57.8(5) . . . . ?
N1 C31 C32 O31 33.2(9) . . . . ?
N1 C31 C32 C31' -62.8(7) . . . . ?
C31' C32 O31 Si1 30.9(4) . . . . ?
C31 C32 O31 Si1 -14.3(7) . . . . ?
O41 Si1 O31 C32 -83.3(3) . . . . ?
O21 Si1 O31 C32 71.6(3) . . . . ?
C11 Si1 O31 C32 173.1(3) . . . . ?
N1 Si1 O31 C32 -5.6(3) . . . . ?
C21' N1 C41 C42 139.6(5) . . . . ?
C31 N1 C41 C42 -117.5(8) . . . . ?
C31' N1 C41 C42 -88.9(4) . . . . ?
C21 N1 C41 C42 123.9(5) . . . . ?
Si1 N1 C41 C42 18.9(5) . . . . ?
N1 C41 C42 O41 -24.6(6) . . . . ?
C41 C42 O41 Si1 19.2(5) . . . . ?
O31 Si1 O41 C42 71.5(3) . . . . ?
O21 Si1 O41 C42 -84.0(3) . . . . ?
C11 Si1 O41 C42 174.0(3) . . . . ?
N1 Si1 O41 C42 -6.1(3) . . . . ?

_refine_diff_density_max         0.508
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-3

# start Validation Reply Form
_vrf_PLAT410_s9                  
;
PROBLEM: Short Intra H...H Contact H21A .. H41A .. 1.52 Ang.
RESPONSE: This alert originates from the highly disordered carbon C21 which is disordered over two positions C21 and C21', with SOFs of 0.5 each. As a result the hydrogen associated with C21 ie. H21A is in close proximity to H41 (hydrogen atom on C41).  This model of refinement 
seems to be the most appropriate one.
;
####################################################################### 
# 
# 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_s7
_database_code_depnum_ccdc_archive 'CCDC 1428621'
_audit_update_record             
;
2016-04-13 deposited with the CCDC.
2016-05-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H27 N O4 S Si'
_chemical_formula_sum            'C22 H27 N O4 S Si'
_chemical_formula_weight         429.59

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   7.2068(2)
_cell_length_b                   8.9671(3)
_cell_length_c                   16.5006(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.3430(10)
_cell_angle_gamma                90
_cell_volume                     1064.52(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    18186
_cell_measurement_theta_min      2.473
_cell_measurement_theta_max      28.386

_exptl_crystal_description       plates
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.237
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   'SADABS (Sheldrick 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18186
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.473
_diffrn_reflns_theta_max         28.386
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5321
_reflns_number_gt                5035
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.880
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.999

_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       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'APEX2 (Bruker, 2013)'
_computing_structure_solution    'SHELXT-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXT-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    Diamond
_computing_publication_material  ?

_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)+(0.0407P)²+0.1161P] 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_abs_structure_details 
;
 Flack x determined using 2263 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.02(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5321
_refine_ls_number_parameters     262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0726
_refine_ls_wR_factor_gt          0.0713
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.80071(7) 0.63753(6) 0.12347(3) 0.02032(11) Uani 1 1 d . . . . .
S1 S 0.16724(7) 0.29321(7) 0.16717(3) 0.03386(14) Uani 1 1 d . . . . .
C1 C 0.2508(3) 0.2095(2) 0.25910(13) 0.0269(4) Uani 1 1 d . . . . .
C2 C 0.1133(3) 0.2015(2) 0.32329(12) 0.0250(4) Uani 1 1 d . . . . .
C3 C 0.1665(3) 0.1306(3) 0.39596(13) 0.0322(4) Uani 1 1 d . . . . .
H3A H 0.2878 0.0896 0.4035 0.039 Uiso 1 1 calc R U . . .
C4 C 0.0444(3) 0.1193(3) 0.45718(12) 0.0321(5) Uani 1 1 d . . . . .
H4A H 0.0827 0.0702 0.5064 0.038 Uiso 1 1 calc R U . . .
C5 C -0.1342(3) 0.1789(2) 0.44791(12) 0.0263(4) Uani 1 1 d . . . . .
C6 C -0.1860(3) 0.2514(3) 0.37501(13) 0.0312(5) Uani 1 1 d . . . . .
H6A H -0.3068 0.2934 0.3675 0.037 Uiso 1 1 calc R U . . .
C7 C -0.0637(3) 0.2627(2) 0.31342(13) 0.0295(4) Uani 1 1 d . . . . .
H7A H -0.1011 0.3124 0.2643 0.035 Uiso 1 1 calc R U . . .
C8 C -0.2656(3) 0.1698(2) 0.51409(12) 0.0266(4) Uani 1 1 d . . . . .
C9 C -0.2724(3) 0.0429(3) 0.56285(13) 0.0313(5) Uani 1 1 d . . . . .
H9A H -0.1943 -0.0397 0.5530 0.038 Uiso 1 1 calc R U . . .
C10 C -0.3921(3) 0.0366(3) 0.62534(14) 0.0362(5) Uani 1 1 d . . . . .
H10A H -0.3950 -0.0501 0.6583 0.043 Uiso 1 1 calc R U . . .
C11 C -0.5079(3) 0.1558(3) 0.64024(13) 0.0392(5) Uani 1 1 d . . . . .
H11A H -0.5890 0.1513 0.6835 0.047 Uiso 1 1 calc R U . . .
C12 C -0.5045(4) 0.2809(3) 0.59173(16) 0.0455(6) Uani 1 1 d . . . . .
H12A H -0.5841 0.3627 0.6013 0.055 Uiso 1 1 calc R U . . .
C13 C -0.3848(3) 0.2875(3) 0.52891(14) 0.0371(5) Uani 1 1 d . . . . .
H13A H -0.3842 0.3737 0.4955 0.044 Uiso 1 1 calc R U . . .
C14 C 0.3807(3) 0.3064(3) 0.11487(13) 0.0301(4) Uani 1 1 d . . . . .
H14A H 0.4580 0.2172 0.1275 0.036 Uiso 1 1 calc R U . . .
H14B H 0.3508 0.3083 0.0556 0.036 Uiso 1 1 calc R U . . .
C15 C 0.4899(3) 0.4453(2) 0.13948(13) 0.0270(4) Uani 1 1 d . . . . .
H15A H 0.5250 0.4401 0.1983 0.032 Uiso 1 1 calc R U . . .
H15B H 0.4090 0.5336 0.1302 0.032 Uiso 1 1 calc R U . . .
C16 C 0.6653(3) 0.4658(2) 0.09330(12) 0.0239(4) Uani 1 1 d . . . . .
H16A H 0.6301 0.4708 0.0345 0.029 Uiso 1 1 calc R U . . .
H16B H 0.7461 0.3775 0.1027 0.029 Uiso 1 1 calc R U . . .
N1 N 0.9594(2) 0.8411(2) 0.16135(11) 0.0287(4) Uani 1 1 d . . . . .
O1 O 0.4087(2) 0.1627(2) 0.26938(10) 0.0429(4) Uani 1 1 d . . . . .
C21 C 0.8445(3) 0.9643(2) 0.12750(17) 0.0389(6) Uani 1 1 d . . . . .
H21A H 0.8781 0.9876 0.0716 0.047 Uiso 1 1 calc R U . . .
H21B H 0.8627 1.0549 0.1613 0.047 Uiso 1 1 calc R U . . .
C22 C 0.6442(3) 0.9116(3) 0.12749(17) 0.0373(5) Uani 1 1 d . . . . .
H22A H 0.5995 0.9185 0.1830 0.045 Uiso 1 1 calc R U . . .
H22B H 0.5641 0.9754 0.0911 0.045 Uiso 1 1 calc R U . . .
O21 O 0.6350(2) 0.76215(16) 0.10029(9) 0.0297(3) Uani 1 1 d . . . . .
C31 C 0.9737(3) 0.8339(3) 0.25064(14) 0.0382(5) Uani 1 1 d . . . . .
H31A H 0.8661 0.8840 0.2736 0.046 Uiso 1 1 calc R U . . .
H31B H 1.0892 0.8828 0.2724 0.046 Uiso 1 1 calc R U . . .
C32 C 0.9756(3) 0.6687(3) 0.27174(13) 0.0369(5) Uani 1 1 d . . . . .
H32A H 1.0998 0.6260 0.2636 0.044 Uiso 1 1 calc R U . . .
H32B H 0.9483 0.6549 0.3294 0.044 Uiso 1 1 calc R U . . .
O31 O 0.8395(2) 0.59536(16) 0.22103(8) 0.0273(3) Uani 1 1 d . . . . .
C41 C 1.1383(3) 0.8244(3) 0.12340(15) 0.0355(5) Uani 1 1 d . . . . .
H41A H 1.2285 0.7700 0.1601 0.043 Uiso 1 1 calc R U . . .
H41B H 1.1909 0.9233 0.1112 0.043 Uiso 1 1 calc R U . . .
C42 C 1.0976(3) 0.7372(3) 0.04600(15) 0.0351(5) Uani 1 1 d . . . . .
H42A H 1.0421 0.8039 0.0033 0.042 Uiso 1 1 calc R U . . .
H42B H 1.2145 0.6958 0.0267 0.042 Uiso 1 1 calc R U . . .
O41 O 0.9725(2) 0.61956(17) 0.06107(8) 0.0301(3) 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
Si1 O31 1.6614(14) . ?
Si1 O41 1.6637(14) . ?
Si1 O21 1.6639(15) . ?
Si1 C16 1.875(2) . ?
Si1 N1 2.2243(18) . ?
S1 C1 1.766(2) . ?
S1 C14 1.811(2) . ?
C1 O1 1.215(3) . ?
C1 C2 1.494(3) . ?
C2 C7 1.389(3) . ?
C2 C3 1.391(3) . ?
C3 C4 1.382(3) . ?
C4 C5 1.394(3) . ?
C5 C6 1.398(3) . ?
C5 C8 1.489(3) . ?
C6 C7 1.387(3) . ?
C8 C13 1.391(3) . ?
C8 C9 1.396(3) . ?
C9 C10 1.383(3) . ?
C10 C11 1.387(4) . ?
C11 C12 1.379(4) . ?
C12 C13 1.388(3) . ?
C14 C15 1.516(3) . ?
C15 C16 1.525(3) . ?
N1 C21 1.471(3) . ?
N1 C31 1.472(3) . ?
N1 C41 1.473(3) . ?
C21 C22 1.519(3) . ?
C22 O21 1.414(3) . ?
C31 C32 1.522(3) . ?
C32 O31 1.413(3) . ?
C41 C42 1.511(3) . ?
C42 O41 1.419(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
O31 Si1 O41 119.22(8) . . ?
O31 Si1 O21 116.98(8) . . ?
O41 Si1 O21 118.23(8) . . ?
O31 Si1 C16 97.24(8) . . ?
O41 Si1 C16 98.67(8) . . ?
O21 Si1 C16 97.76(8) . . ?
O31 Si1 N1 81.93(7) . . ?
O41 Si1 N1 82.20(7) . . ?
O21 Si1 N1 82.18(7) . . ?
C16 Si1 N1 179.02(8) . . ?
C1 S1 C14 100.40(10) . . ?
O1 C1 C2 122.6(2) . . ?
O1 C1 S1 122.41(17) . . ?
C2 C1 S1 114.98(15) . . ?
C7 C2 C3 119.12(19) . . ?
C7 C2 C1 122.71(18) . . ?
C3 C2 C1 118.17(19) . . ?
C4 C3 C2 120.5(2) . . ?
C3 C4 C5 121.01(19) . . ?
C4 C5 C6 118.11(19) . . ?
C4 C5 C8 121.41(18) . . ?
C6 C5 C8 120.47(19) . . ?
C7 C6 C5 121.0(2) . . ?
C6 C7 C2 120.23(19) . . ?
C13 C8 C9 118.30(19) . . ?
C13 C8 C5 120.85(18) . . ?
C9 C8 C5 120.84(19) . . ?
C10 C9 C8 120.5(2) . . ?
C9 C10 C11 120.5(2) . . ?
C12 C11 C10 119.5(2) . . ?
C11 C12 C13 120.1(2) . . ?
C12 C13 C8 121.1(2) . . ?
C15 C14 S1 111.60(15) . . ?
C14 C15 C16 113.45(16) . . ?
C15 C16 Si1 113.60(13) . . ?
C21 N1 C31 114.69(19) . . ?
C21 N1 C41 113.71(18) . . ?
C31 N1 C41 114.15(18) . . ?
C21 N1 Si1 103.93(13) . . ?
C31 N1 Si1 104.47(13) . . ?
C41 N1 Si1 104.20(13) . . ?
N1 C21 C22 106.28(18) . . ?
O21 C22 C21 108.79(19) . . ?
C22 O21 Si1 122.95(14) . . ?
N1 C31 C32 105.72(18) . . ?
O31 C32 C31 108.69(18) . . ?
C32 O31 Si1 122.66(13) . . ?
N1 C41 C42 106.28(17) . . ?
O41 C42 C41 109.29(18) . . ?
C42 O41 Si1 122.67(14) . . ?

_refine_diff_density_max         0.288
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-3

