# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_130906_wsz_2_91_3
_database_code_depnum_ccdc_archive 'CCDC 979559'
_audit_update_record             
;
2014-01-03 deposited with the CCDC.
2015-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H23 N O Si, H2 O'
_chemical_formula_sum            'C17 H25 N O2 Si'
_chemical_formula_weight         303.47

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   7.8451(6)
_cell_length_b                   10.8055(10)
_cell_length_c                   41.681(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.188(5)
_cell_angle_gamma                90.00
_cell_volume                     3530.7(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2943
_cell_measurement_theta_min      2.8054
_cell_measurement_theta_max      29.4993

_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9497
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_process_details   
;
CrysAlis PRO (Agilent Technologies, 2011) 
;

_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  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3592
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15620
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0619
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         25.35
_reflns_number_total             6440
_reflns_number_gt                4214
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0876P)²+7.5774P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6440
_refine_ls_number_parameters     401
_refine_ls_number_restraints     76
_refine_ls_R_factor_all          0.1392
_refine_ls_R_factor_gt           0.1006
_refine_ls_wR_factor_ref         0.2672
_refine_ls_wR_factor_gt          0.2419
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.2312(2) 0.89884(17) 0.05838(4) 0.0674(5) Uani 1 1 d U . .
Si2 Si 0.7175(3) 0.40098(19) 0.06095(4) 0.0754(6) Uani 1 1 d U . .
O1 O 0.1635(4) 1.0279(4) 0.23139(8) 0.0542(9) Uani 1 1 d . . .
O2 O 0.6640(4) 0.2902(4) 0.23400(8) 0.0544(9) Uani 1 1 d . . .
O3 O 0.4946(5) 0.7414(4) 0.24389(11) 0.0683(12) Uani 1 1 d D . .
H3A H 0.597(3) 0.759(5) 0.2491(11) 0.049(14) Uiso 1 1 d D . .
H3B H 0.471(6) 0.676(3) 0.2540(11) 0.049(15) Uiso 1 1 d D . .
O4 O -0.0024(6) 0.5714(4) 0.24540(11) 0.0702(12) Uani 1 1 d D . .
H4A H 0.103(4) 0.587(8) 0.2485(17) 0.11(3) Uiso 1 1 d D . .
H4B H -0.051(11) 0.632(6) 0.2543(19) 0.15(4) Uiso 1 1 d D . .
N1 N 0.2309(5) 0.8531(4) 0.20583(9) 0.0460(10) Uani 1 1 d . . .
H1 H 0.3223 0.8483 0.2178 0.055 Uiso 1 1 calc R . .
N2 N 0.7301(5) 0.4637(4) 0.20772(8) 0.0415(9) Uani 1 1 d . . .
H2 H 0.8205 0.4703 0.2199 0.050 Uiso 1 1 calc R . .
C1 C 0.0111(5) 0.9861(4) 0.15333(10) 0.0377(10) Uani 1 1 d . . .
C2 C -0.1326(6) 1.0007(5) 0.13313(11) 0.0463(12) Uani 1 1 d . . .
H2A H -0.1193 1.0086 0.1111 0.056 Uiso 1 1 calc R . .
C3 C -0.2935(6) 1.0038(5) 0.14488(13) 0.0541(13) Uani 1 1 d . . .
H3 H -0.3879 1.0123 0.1309 0.065 Uiso 1 1 calc R . .
C4 C -0.3153(6) 0.9943(5) 0.17712(13) 0.0553(13) Uani 1 1 d . . .
H4 H -0.4242 0.9987 0.1851 0.066 Uiso 1 1 calc R . .
C5 C -0.1763(6) 0.9781(5) 0.19790(12) 0.0508(13) Uani 1 1 d . . .
H5 H -0.1915 0.9710 0.2198 0.061 Uiso 1 1 calc R . .
C6 C -0.0129(5) 0.9724(4) 0.18604(10) 0.0395(10) Uani 1 1 d . . .
C7 C 0.1346(5) 0.9527(5) 0.20941(10) 0.0413(11) Uani 1 1 d . . .
C8 C 0.1973(6) 0.7508(4) 0.18354(11) 0.0445(11) Uani 1 1 d . . .
H8A H 0.0759 0.7481 0.1782 0.053 Uiso 1 1 calc R . .
H8B H 0.2279 0.6738 0.1942 0.053 Uiso 1 1 calc R . .
C9 C 0.2935(6) 0.7596(4) 0.15259(11) 0.0415(11) Uani 1 1 d . . .
H9 H 0.4140 0.7735 0.1586 0.050 Uiso 1 1 calc R . .
C10 C 0.2830(6) 0.6409(5) 0.13254(12) 0.0480(12) Uani 1 1 d . . .
H10A H 0.3721 0.5834 0.1394 0.058 Uiso 1 1 calc R . .
H10B H 0.1731 0.6011 0.1346 0.058 Uiso 1 1 calc R . .
C11 C 0.3066(6) 0.6827(5) 0.09811(12) 0.0523(13) Uani 1 1 d . . .
H11A H 0.2350 0.6350 0.0832 0.063 Uiso 1 1 calc R . .
H11B H 0.4246 0.6741 0.0923 0.063 Uiso 1 1 calc R . .
C12 C 0.2523(6) 0.8201(5) 0.09812(11) 0.0470(12) Uani 1 1 d . . .
C13 C 0.2406(5) 0.8582(4) 0.12826(11) 0.0393(10) Uani 1 1 d . . .
C14 C 0.1873(6) 0.9840(4) 0.13934(11) 0.0425(11) Uani 1 1 d . . .
H14A H 0.1884 1.0408 0.1213 0.051 Uiso 1 1 calc R . .
H14B H 0.2700 1.0134 0.1555 0.051 Uiso 1 1 calc R . .
C15 C 0.0216(12) 0.8567(10) 0.03845(19) 0.132(3) Uani 1 1 d U . .
H15A H 0.0027 0.7694 0.0406 0.197 Uiso 1 1 calc R . .
H15B H 0.0226 0.8780 0.0161 0.197 Uiso 1 1 calc R . .
H15C H -0.0682 0.9012 0.0484 0.197 Uiso 1 1 calc R . .
C16 C 0.4061(13) 0.8438(11) 0.03346(19) 0.138(3) Uani 1 1 d U . .
H16A H 0.5138 0.8606 0.0443 0.207 Uiso 1 1 calc R . .
H16B H 0.4006 0.8859 0.0132 0.207 Uiso 1 1 calc R . .
H16C H 0.3945 0.7563 0.0300 0.207 Uiso 1 1 calc R . .
C17 C 0.2441(12) 1.0695(8) 0.05936(17) 0.110(3) Uani 1 1 d U . .
H17A H 0.1431 1.1024 0.0685 0.165 Uiso 1 1 calc R . .
H17B H 0.2533 1.1004 0.0379 0.165 Uiso 1 1 calc R . .
H17C H 0.3424 1.0943 0.0722 0.165 Uiso 1 1 calc R . .
C18 C 0.5105(5) 0.3252(4) 0.15619(10) 0.0377(10) Uani 1 1 d . . .
C19 C 0.3665(6) 0.3041(5) 0.13631(11) 0.0466(12) Uani 1 1 d . . .
H19 H 0.3799 0.2899 0.1145 0.056 Uiso 1 1 calc R . .
C20 C 0.2052(6) 0.3039(5) 0.14809(12) 0.0500(12) Uani 1 1 d . . .
H20 H 0.1107 0.2918 0.1343 0.060 Uiso 1 1 calc R . .
C21 C 0.1840(6) 0.3215(5) 0.18024(12) 0.0523(13) Uani 1 1 d . . .
H21 H 0.0749 0.3210 0.1882 0.063 Uiso 1 1 calc R . .
C22 C 0.3228(6) 0.3398(5) 0.20066(11) 0.0485(12) Uani 1 1 d . . .
H22 H 0.3082 0.3495 0.2226 0.058 Uiso 1 1 calc R . .
C23 C 0.4855(5) 0.3438(4) 0.18857(10) 0.0377(10) Uani 1 1 d . . .
C24 C 0.6343(6) 0.3637(5) 0.21175(10) 0.0417(11) Uani 1 1 d . . .
C25 C 0.6970(6) 0.5630(5) 0.18471(10) 0.0438(11) Uani 1 1 d . . .
H25A H 0.7270 0.6413 0.1948 0.053 Uiso 1 1 calc R . .
H25B H 0.5758 0.5650 0.1792 0.053 Uiso 1 1 calc R . .
C26 C 0.7944(6) 0.5507(4) 0.15406(11) 0.0424(11) Uani 1 1 d . . .
H26 H 0.9150 0.5369 0.1600 0.051 Uiso 1 1 calc R . .
C27 C 0.7812(6) 0.6676(5) 0.13314(12) 0.0519(13) Uani 1 1 d . . .
H27A H 0.6708 0.7068 0.1350 0.062 Uiso 1 1 calc R . .
H27B H 0.8696 0.7266 0.1395 0.062 Uiso 1 1 calc R . .
C28 C 0.8044(7) 0.6226(6) 0.09912(12) 0.0579(14) Uani 1 1 d . . .
H28A H 0.9226 0.6294 0.0934 0.069 Uiso 1 1 calc R . .
H28B H 0.7340 0.6699 0.0839 0.069 Uiso 1 1 calc R . .
C29 C 0.7478(6) 0.4873(5) 0.09978(12) 0.0521(13) Uani 1 1 d . . .
C30 C 0.7376(5) 0.4504(5) 0.13040(10) 0.0408(11) Uani 1 1 d . . .
C31 C 0.6857(6) 0.3235(4) 0.14217(11) 0.0438(11) Uani 1 1 d . . .
H31A H 0.6858 0.2655 0.1244 0.053 Uiso 1 1 calc R . .
H31B H 0.7686 0.2952 0.1584 0.053 Uiso 1 1 calc R . .
C32 C 0.7529(13) 0.2300(8) 0.06363(18) 0.123(3) Uani 1 1 d U . .
H32A H 0.8670 0.2140 0.0717 0.185 Uiso 1 1 calc R . .
H32B H 0.7367 0.1938 0.0427 0.185 Uiso 1 1 calc R . .
H32C H 0.6730 0.1945 0.0779 0.185 Uiso 1 1 calc R . .
C33 C 0.4906(12) 0.4153(10) 0.04514(19) 0.126(3) Uani 1 1 d U . .
H33A H 0.4147 0.3895 0.0614 0.189 Uiso 1 1 calc R . .
H33B H 0.4740 0.3639 0.0265 0.189 Uiso 1 1 calc R . .
H33C H 0.4673 0.4999 0.0395 0.189 Uiso 1 1 calc R . .
C34 C 0.8532(15) 0.4728(12) 0.0320(2) 0.162(4) Uani 1 1 d U . .
H34A H 0.8232 0.5585 0.0297 0.243 Uiso 1 1 calc R . .
H34B H 0.8382 0.4318 0.0117 0.243 Uiso 1 1 calc R . .
H34C H 0.9703 0.4662 0.0394 0.243 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
Si1 C17 1.847(9) . ?
Si1 C16 1.851(8) . ?
Si1 C12 1.864(5) . ?
Si1 C15 1.870(8) . ?
Si2 C34 1.813(9) . ?
Si2 C32 1.871(9) . ?
Si2 C29 1.875(6) . ?
Si2 C33 1.881(9) . ?
O1 C7 1.239(6) . ?
O2 C24 1.236(6) . ?
O3 H3A 0.85(2) . ?
O3 H3B 0.85(2) . ?
O4 H4A 0.85(2) . ?
O4 H4B 0.85(2) . ?
N1 C7 1.326(6) . ?
N1 C8 1.461(6) . ?
N1 H1 0.8600 . ?
N2 C24 1.331(6) . ?
N2 C25 1.457(6) . ?
N2 H2 0.8600 . ?
C1 C2 1.390(6) . ?
C1 C6 1.391(6) . ?
C1 C14 1.521(6) . ?
C2 C3 1.372(7) . ?
C2 H2A 0.9300 . ?
C3 C4 1.365(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.499(6) . ?
C8 C9 1.522(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C13 1.518(6) . ?
C9 C10 1.531(7) . ?
C9 H9 0.9800 . ?
C10 C11 1.522(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.546(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.328(6) . ?
C13 C14 1.501(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C23 1.386(6) . ?
C18 C19 1.394(6) . ?
C18 C31 1.514(6) . ?
C19 C20 1.375(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.370(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.371(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.391(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.502(6) . ?
C25 C26 1.519(6) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C30 1.520(6) . ?
C26 C27 1.537(7) . ?
C26 H26 0.9800 . ?
C27 C28 1.516(7) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.529(8) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.342(6) . ?
C30 C31 1.517(6) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 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
C17 Si1 C16 107.0(5) . . ?
C17 Si1 C12 115.7(3) . . ?
C16 Si1 C12 108.0(3) . . ?
C17 Si1 C15 107.4(5) . . ?
C16 Si1 C15 109.3(5) . . ?
C12 Si1 C15 109.3(3) . . ?
C34 Si2 C32 111.9(5) . . ?
C34 Si2 C29 107.6(4) . . ?
C32 Si2 C29 115.2(3) . . ?
C34 Si2 C33 107.7(5) . . ?
C32 Si2 C33 103.8(5) . . ?
C29 Si2 C33 110.4(3) . . ?
H3A O3 H3B 106(5) . . ?
H4A O4 H4B 103(8) . . ?
C7 N1 C8 126.5(4) . . ?
C7 N1 H1 116.7 . . ?
C8 N1 H1 116.7 . . ?
C24 N2 C25 126.5(4) . . ?
C24 N2 H2 116.8 . . ?
C25 N2 H2 116.8 . . ?
C2 C1 C6 118.0(4) . . ?
C2 C1 C14 119.8(4) . . ?
C6 C1 C14 122.2(4) . . ?
C3 C2 C1 121.5(5) . . ?
C3 C2 H2A 119.3 . . ?
C1 C2 H2A 119.3 . . ?
C4 C3 C2 120.1(5) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.2(5) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.0(5) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 120.2(4) . . ?
C1 C6 C7 121.5(4) . . ?
C5 C6 C7 118.3(4) . . ?
O1 C7 N1 121.8(4) . . ?
O1 C7 C6 120.1(4) . . ?
N1 C7 C6 118.1(4) . . ?
N1 C8 C9 114.1(4) . . ?
N1 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
N1 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C13 C9 C8 118.6(4) . . ?
C13 C9 C10 102.5(4) . . ?
C8 C9 C10 113.1(4) . . ?
C13 C9 H9 107.4 . . ?
C8 C9 H9 107.4 . . ?
C10 C9 H9 107.4 . . ?
C11 C10 C9 105.1(4) . . ?
C11 C10 H10A 110.7 . . ?
C9 C10 H10A 110.7 . . ?
C11 C10 H10B 110.7 . . ?
C9 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
C10 C11 C12 104.0(4) . . ?
C10 C11 H11A 111.0 . . ?
C12 C11 H11A 111.0 . . ?
C10 C11 H11B 111.0 . . ?
C12 C11 H11B 111.0 . . ?
H11A C11 H11B 109.0 . . ?
C13 C12 C11 109.1(4) . . ?
C13 C12 Si1 133.8(4) . . ?
C11 C12 Si1 117.0(3) . . ?
C12 C13 C14 127.0(4) . . ?
C12 C13 C9 112.8(4) . . ?
C14 C13 C9 120.2(4) . . ?
C13 C14 C1 113.5(4) . . ?
C13 C14 H14A 108.9 . . ?
C1 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C1 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
Si1 C15 H15A 109.5 . . ?
Si1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
Si1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Si1 C16 H16A 109.5 . . ?
Si1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
Si1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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 . . ?
C23 C18 C19 117.4(4) . . ?
C23 C18 C31 122.8(4) . . ?
C19 C18 C31 119.7(4) . . ?
C20 C19 C18 121.6(4) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C21 C20 C19 119.8(4) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 120.3(4) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C23 119.9(4) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C18 C23 C22 121.0(4) . . ?
C18 C23 C24 120.8(4) . . ?
C22 C23 C24 118.2(4) . . ?
O2 C24 N2 121.7(4) . . ?
O2 C24 C23 120.7(4) . . ?
N2 C24 C23 117.6(4) . . ?
N2 C25 C26 114.0(4) . . ?
N2 C25 H25A 108.8 . . ?
C26 C25 H25A 108.8 . . ?
N2 C25 H25B 108.8 . . ?
C26 C25 H25B 108.8 . . ?
H25A C25 H25B 107.7 . . ?
C25 C26 C30 117.6(4) . . ?
C25 C26 C27 112.3(4) . . ?
C30 C26 C27 101.9(4) . . ?
C25 C26 H26 108.2 . . ?
C30 C26 H26 108.2 . . ?
C27 C26 H26 108.2 . . ?
C28 C27 C26 105.0(4) . . ?
C28 C27 H27A 110.7 . . ?
C26 C27 H27A 110.7 . . ?
C28 C27 H27B 110.7 . . ?
C26 C27 H27B 110.7 . . ?
H27A C27 H27B 108.8 . . ?
C27 C28 C29 104.2(4) . . ?
C27 C28 H28A 110.9 . . ?
C29 C28 H28A 110.9 . . ?
C27 C28 H28B 110.9 . . ?
C29 C28 H28B 110.9 . . ?
H28A C28 H28B 108.9 . . ?
C30 C29 C28 109.2(5) . . ?
C30 C29 Si2 131.5(4) . . ?
C28 C29 Si2 119.2(4) . . ?
C29 C30 C31 127.0(5) . . ?
C29 C30 C26 112.3(4) . . ?
C31 C30 C26 120.7(4) . . ?
C18 C31 C30 111.9(4) . . ?
C18 C31 H31A 109.2 . . ?
C30 C31 H31A 109.2 . . ?
C18 C31 H31B 109.2 . . ?
C30 C31 H31B 109.2 . . ?
H31A C31 H31B 107.9 . . ?
Si2 C32 H32A 109.5 . . ?
Si2 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
Si2 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
Si2 C33 H33A 109.5 . . ?
Si2 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
Si2 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
Si2 C34 H34A 109.5 . . ?
Si2 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
Si2 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.062
####################################################################### 
# 
# 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_140306_wsz_3_134
_database_code_depnum_ccdc_archive 'CCDC 990983'
_audit_update_record             
;
2014-03-11 deposited with the CCDC.
2015-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H17 N O S, C H2 Cl2 '
_chemical_formula_sum            'C19 H19 Cl2 N O S'
_chemical_formula_weight         380.31

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   9.4678(14)
_cell_length_b                   22.465(3)
_cell_length_c                   8.4857(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.892(15)
_cell_angle_gamma                90.00
_cell_volume                     1798.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    2167
_cell_measurement_theta_min      2.8112
_cell_measurement_theta_max      29.4107

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8492
_exptl_absorpt_correction_T_max  0.8971
_exptl_absorpt_process_details   
;
CrysAlis PRO (Agilent Technologies, 2011) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      170(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  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3592
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7449
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         25.35
_reflns_number_total             3290
_reflns_number_gt                2578
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.1035P)²+3.0111P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3290
_refine_ls_number_parameters     217
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0646
_refine_ls_wR_factor_ref         0.1993
_refine_ls_wR_factor_gt          0.1837
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.43611(15) 0.52014(6) -0.28413(18) 0.0644(4) Uani 1 1 d . . .
Cl2 Cl 0.44010(12) 0.64056(5) -0.15278(14) 0.0507(4) Uani 1 1 d . . .
S1 S -0.11009(15) 0.94114(5) 0.14833(16) 0.0563(4) Uani 1 1 d U . .
O1 O 0.1813(3) 0.53130(11) 0.0346(3) 0.0329(6) Uani 1 1 d . . .
N1 N -0.0262(3) 0.56827(13) 0.1049(4) 0.0269(7) Uani 1 1 d . . .
H1 H -0.0712 0.5427 0.0401 0.032 Uiso 1 1 calc R . .
C1 C 0.1952(3) 0.61829(15) 0.1957(4) 0.0227(7) Uani 1 1 d . . .
C2 C 0.3014(4) 0.59978(16) 0.3097(4) 0.0285(8) Uani 1 1 d . . .
H2 H 0.3188 0.5585 0.3260 0.034 Uiso 1 1 calc R . .
C3 C 0.3815(4) 0.64116(17) 0.3992(4) 0.0304(8) Uani 1 1 d . . .
H3 H 0.4514 0.6284 0.4789 0.036 Uiso 1 1 calc R . .
C4 C 0.3588(4) 0.70157(17) 0.3713(4) 0.0285(8) Uani 1 1 d . . .
H4 H 0.4138 0.7303 0.4316 0.034 Uiso 1 1 calc R . .
C5 C 0.2555(3) 0.71984(15) 0.2553(4) 0.0231(7) Uani 1 1 d . . .
H5 H 0.2422 0.7612 0.2360 0.028 Uiso 1 1 calc R . .
C6 C 0.1711(3) 0.67926(14) 0.1667(4) 0.0195(7) Uani 1 1 d . . .
C7 C 0.0606(3) 0.70158(15) 0.0397(4) 0.0209(7) Uani 1 1 d . . .
H7A H 0.0947 0.7392 -0.0047 0.025 Uiso 1 1 calc R . .
H7B H 0.0502 0.6720 -0.0470 0.025 Uiso 1 1 calc R . .
C8 C -0.0833(3) 0.71238(15) 0.1002(4) 0.0201(7) Uani 1 1 d . . .
C9 C -0.1821(3) 0.65954(15) 0.1174(4) 0.0231(7) Uani 1 1 d . . .
H9 H -0.2239 0.6474 0.0100 0.028 Uiso 1 1 calc R . .
C10 C -0.1143(4) 0.60475(15) 0.2017(4) 0.0246(7) Uani 1 1 d . . .
H10A H -0.0551 0.6183 0.2967 0.030 Uiso 1 1 calc R . .
H10B H -0.1907 0.5794 0.2380 0.030 Uiso 1 1 calc R . .
C11 C 0.1143(4) 0.56976(15) 0.1047(4) 0.0249(8) Uani 1 1 d . . .
C12 C -0.2998(4) 0.68534(16) 0.2101(4) 0.0277(8) Uani 1 1 d . . .
H12A H -0.3932 0.6690 0.1701 0.033 Uiso 1 1 calc R . .
H12B H -0.2826 0.6757 0.3239 0.033 Uiso 1 1 calc R . .
C13 C -0.2951(3) 0.75272(17) 0.1841(4) 0.0285(8) Uani 1 1 d . . .
H13A H -0.3672 0.7651 0.0990 0.034 Uiso 1 1 calc R . .
H13B H -0.3120 0.7744 0.2823 0.034 Uiso 1 1 calc R . .
C14 C -0.1456(3) 0.76429(15) 0.1367(4) 0.0218(7) Uani 1 1 d . . .
C15 C -0.0971(4) 0.82650(15) 0.1312(4) 0.0234(7) Uani 1 1 d . . .
C16 C 0.0400(4) 0.84922(16) 0.1060(4) 0.0292(8) Uani 1 1 d . . .
H16 H 0.1179 0.8247 0.0849 0.035 Uiso 1 1 calc R . .
C17 C 0.0484(3) 0.91675(14) 0.1163(3) 0.0192(6) Uani 1 1 d U . .
H17 H 0.1302 0.9404 0.1061 0.023 Uiso 1 1 calc R . .
C18 C -0.1891(4) 0.87346(18) 0.1548(5) 0.0342(8) Uani 1 1 d U . .
H18 H -0.2860 0.8682 0.1727 0.041 Uiso 1 1 calc R . .
C19 C 0.4661(5) 0.5641(2) -0.1115(5) 0.0467(11) Uani 1 1 d . . .
H19A H 0.4006 0.5514 -0.0330 0.056 Uiso 1 1 calc R . .
H19B H 0.5643 0.5577 -0.0647 0.056 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
Cl1 C19 1.770(5) . ?
Cl2 C19 1.766(4) . ?
S1 C17 1.642(4) . ?
S1 C18 1.697(4) . ?
O1 C11 1.252(4) . ?
N1 C11 1.331(4) . ?
N1 C10 1.469(4) . ?
N1 H1 0.8800 . ?
C1 C2 1.398(5) . ?
C1 C6 1.407(5) . ?
C1 C11 1.507(5) . ?
C2 C3 1.385(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.522(4) . ?
C7 C8 1.516(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C14 1.355(5) . ?
C8 C9 1.526(5) . ?
C9 C12 1.531(5) . ?
C9 C10 1.536(5) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C12 C13 1.531(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.527(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.473(5) . ?
C15 C18 1.393(5) . ?
C15 C16 1.428(5) . ?
C16 C17 1.521(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 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
C17 S1 C18 96.77(18) . . ?
C11 N1 C10 127.0(3) . . ?
C11 N1 H1 116.5 . . ?
C10 N1 H1 116.5 . . ?
C2 C1 C6 120.5(3) . . ?
C2 C1 C11 116.3(3) . . ?
C6 C1 C11 123.2(3) . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 121.8(3) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 117.8(3) . . ?
C5 C6 C7 119.7(3) . . ?
C1 C6 C7 122.4(3) . . ?
C8 C7 C6 113.4(3) . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C14 C8 C7 129.5(3) . . ?
C14 C8 C9 111.4(3) . . ?
C7 C8 C9 118.9(3) . . ?
C8 C9 C12 103.5(3) . . ?
C8 C9 C10 115.6(3) . . ?
C12 C9 C10 111.0(3) . . ?
C8 C9 H9 108.8 . . ?
C12 C9 H9 108.8 . . ?
C10 C9 H9 108.8 . . ?
N1 C10 C9 114.9(3) . . ?
N1 C10 H10A 108.5 . . ?
C9 C10 H10A 108.5 . . ?
N1 C10 H10B 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
O1 C11 N1 122.0(3) . . ?
O1 C11 C1 119.1(3) . . ?
N1 C11 C1 118.8(3) . . ?
C13 C12 C9 105.6(3) . . ?
C13 C12 H12A 110.6 . . ?
C9 C12 H12A 110.6 . . ?
C13 C12 H12B 110.6 . . ?
C9 C12 H12B 110.6 . . ?
H12A C12 H12B 108.7 . . ?
C14 C13 C12 104.2(3) . . ?
C14 C13 H13A 110.9 . . ?
C12 C13 H13A 110.9 . . ?
C14 C13 H13B 110.9 . . ?
C12 C13 H13B 110.9 . . ?
H13A C13 H13B 108.9 . . ?
C8 C14 C15 131.8(3) . . ?
C8 C14 C13 110.2(3) . . ?
C15 C14 C13 117.9(3) . . ?
C18 C15 C16 109.8(3) . . ?
C18 C15 C14 120.9(3) . . ?
C16 C15 C14 129.3(3) . . ?
C15 C16 C17 113.1(3) . . ?
C15 C16 H16 123.5 . . ?
C17 C16 H16 123.5 . . ?
C16 C17 S1 107.4(2) . . ?
C16 C17 H17 126.3 . . ?
S1 C17 H17 126.3 . . ?
C15 C18 S1 113.0(3) . . ?
C15 C18 H18 123.5 . . ?
S1 C18 H18 123.5 . . ?
Cl2 C19 Cl1 111.7(2) . . ?
Cl2 C19 H19A 109.3 . . ?
Cl1 C19 H19A 109.3 . . ?
Cl2 C19 H19B 109.3 . . ?
Cl1 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.231
_refine_diff_density_min         -0.802
_refine_diff_density_rms         0.086
