# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1515998'
_audit_update_record             
;
2016-11-09 deposited with the CCDC.
2017-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H24 S4 Si2'
_chemical_formula_weight         472.83

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'
S S 0.1246 0.1234 '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   '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                   10.5479(13)
_cell_length_b                   16.600(2)
_cell_length_c                   13.9079(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.242(2)
_cell_angle_gamma                90.00
_cell_volume                     2433.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3826
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      24.67

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.496
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8301
_exptl_absorpt_correction_T_max  0.9161
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12295
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4294
_reflns_number_gt                3374
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0665P)²+1.2961P] 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         4294
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1333
_refine_ls_wR_factor_gt          0.1207
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
S1 S -0.06398(8) 0.19567(5) 0.80677(6) 0.0586(2) Uani 1 1 d . . .
S3 S 0.25077(9) -0.11045(5) 0.95537(6) 0.0657(3) Uani 1 1 d . . .
S4 S 0.56000(7) 0.19788(5) 0.82360(6) 0.0551(2) Uani 1 1 d . . .
S2 S 0.24965(10) 0.23231(6) 1.20219(6) 0.0691(3) Uani 1 1 d . . .
Si1 Si -0.00188(10) 0.34291(6) 0.93863(7) 0.0636(3) Uani 1 1 d . . .
Si2 Si 0.52820(10) 0.03369(6) 0.72648(7) 0.0628(3) Uani 1 1 d . . .
C16 C 0.3161(3) 0.03374(15) 0.91528(18) 0.0385(6) Uani 1 1 d . . .
C14 C 0.4799(3) 0.10722(17) 0.8206(2) 0.0440(6) Uani 1 1 d . . .
C7 C 0.0121(3) 0.10537(18) 0.8140(2) 0.0483(7) Uani 1 1 d . . .
H7 H -0.0039 0.0627 0.7720 0.058 Uiso 1 1 calc R . .
C6 C 0.0998(2) 0.10318(16) 0.88922(18) 0.0388(6) Uani 1 1 d . . .
C15 C 0.3947(2) 0.10488(15) 0.89358(18) 0.0373(6) Uani 1 1 d . . .
C13 C 0.4826(3) 0.23185(18) 0.9193(2) 0.0481(7) Uani 1 1 d . . .
H13 H 0.4971 0.2819 0.9478 0.058 Uiso 1 1 calc R . .
C9 C 0.1338(3) 0.21049(17) 1.1181(2) 0.0523(7) Uani 1 1 d . . .
H9 H 0.0476 0.2119 1.1298 0.063 Uiso 1 1 calc R . .
C10 C 0.3171(3) 0.19175(15) 1.03384(19) 0.0425(6) Uani 1 1 d . . .
C17 C 0.1802(3) 0.03302(15) 0.91308(18) 0.0392(6) Uani 1 1 d . . .
C8 C 0.1815(3) 0.19058(15) 1.03059(19) 0.0405(6) Uani 1 1 d . . .
C19 C 0.3654(3) -0.04058(17) 0.9370(2) 0.0506(7) Uani 1 1 d . . .
H19 H 0.4518 -0.0517 0.9413 0.061 Uiso 1 1 calc R . .
C4 C 0.0188(3) 0.23458(17) 0.9050(2) 0.0452(7) Uani 1 1 d . . .
C5 C 0.1013(2) 0.17709(16) 0.94215(18) 0.0383(6) Uani 1 1 d . . .
C12 C 0.3959(3) 0.17718(15) 0.95015(19) 0.0401(6) Uani 1 1 d . . .
C11 C 0.3653(3) 0.21399(18) 1.1227(2) 0.0553(8) Uani 1 1 d . . .
H11 H 0.4516 0.2186 1.1381 0.066 Uiso 1 1 calc R . .
C18 C 0.1340(3) -0.04186(17) 0.9324(2) 0.0525(8) Uani 1 1 d . . .
H18 H 0.0480 -0.0540 0.9329 0.063 Uiso 1 1 calc R . .
C22 C 0.4068(5) -0.0443(3) 0.6977(3) 0.1169(19) Uani 1 1 d . . .
H22A H 0.3290 -0.0187 0.6764 0.175 Uiso 1 1 calc R . .
H22B H 0.3925 -0.0758 0.7541 0.175 Uiso 1 1 calc R . .
H22C H 0.4360 -0.0787 0.6476 0.175 Uiso 1 1 calc R . .
C2 C -0.1278(5) 0.3518(3) 1.0282(3) 0.1119(18) Uani 1 1 d . . .
H2A H -0.1329 0.4067 1.0497 0.168 Uiso 1 1 calc R . .
H2B H -0.1075 0.3175 1.0822 0.168 Uiso 1 1 calc R . .
H2C H -0.2078 0.3359 0.9990 0.168 Uiso 1 1 calc R . .
C20 C 0.5508(5) 0.0906(3) 0.6129(3) 0.1071(16) Uani 1 1 d . . .
H20A H 0.6130 0.1321 0.6242 0.161 Uiso 1 1 calc R . .
H20B H 0.4718 0.1145 0.5915 0.161 Uiso 1 1 calc R . .
H20C H 0.5793 0.0544 0.5643 0.161 Uiso 1 1 calc R . .
C3 C 0.1530(5) 0.3864(2) 0.9845(4) 0.1097(17) Uani 1 1 d . . .
H3A H 0.2205 0.3657 0.9473 0.165 Uiso 1 1 calc R . .
H3B H 0.1674 0.3719 1.0508 0.165 Uiso 1 1 calc R . .
H3C H 0.1503 0.4441 0.9788 0.165 Uiso 1 1 calc R . .
C21 C 0.6827(4) -0.0110(3) 0.7708(4) 0.1122(17) Uani 1 1 d . . .
H21A H 0.7177 -0.0428 0.7206 0.168 Uiso 1 1 calc R . .
H21B H 0.6688 -0.0445 0.8256 0.168 Uiso 1 1 calc R . .
H21C H 0.7407 0.0315 0.7888 0.168 Uiso 1 1 calc R . .
C1 C -0.0510(5) 0.3987(3) 0.8287(3) 0.1009(15) Uani 1 1 d . . .
H1A H 0.0136 0.3940 0.7823 0.151 Uiso 1 1 calc R . .
H1B H -0.0630 0.4545 0.8442 0.151 Uiso 1 1 calc R . .
H1C H -0.1290 0.3767 0.8024 0.151 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 C7 1.702(3) . ?
S1 C4 1.719(3) . ?
S3 C18 1.698(3) . ?
S3 C19 1.702(3) . ?
S4 C13 1.686(3) . ?
S4 C14 1.726(3) . ?
S2 C9 1.698(3) . ?
S2 C11 1.705(3) . ?
Si1 C1 1.844(4) . ?
Si1 C2 1.862(4) . ?
Si1 C4 1.873(3) . ?
Si1 C3 1.875(5) . ?
Si2 C22 1.853(4) . ?
Si2 C20 1.864(4) . ?
Si2 C21 1.872(5) . ?
Si2 C14 1.875(3) . ?
C16 C19 1.368(4) . ?
C16 C17 1.432(4) . ?
C16 C15 1.481(4) . ?
C14 C15 1.382(4) . ?
C7 C6 1.369(4) . ?
C7 H7 0.9300 . ?
C6 C5 1.431(4) . ?
C6 C17 1.471(4) . ?
C15 C12 1.435(4) . ?
C13 C12 1.369(4) . ?
C13 H13 0.9300 . ?
C9 C8 1.375(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.369(4) . ?
C10 C8 1.429(4) . ?
C10 C12 1.477(4) . ?
C17 C18 1.366(4) . ?
C8 C5 1.483(4) . ?
C19 H19 0.9300 . ?
C4 C5 1.378(4) . ?
C11 H11 0.9300 . ?
C18 H18 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
C7 S1 C4 93.43(14) . . ?
C18 S3 C19 91.65(15) . . ?
C13 S4 C14 93.39(14) . . ?
C9 S2 C11 91.67(15) . . ?
C1 Si1 C2 109.3(2) . . ?
C1 Si1 C4 107.89(17) . . ?
C2 Si1 C4 109.67(18) . . ?
C1 Si1 C3 107.5(2) . . ?
C2 Si1 C3 112.1(3) . . ?
C4 Si1 C3 110.26(17) . . ?
C22 Si2 C20 106.3(3) . . ?
C22 Si2 C21 112.3(3) . . ?
C20 Si2 C21 109.9(2) . . ?
C22 Si2 C14 113.66(18) . . ?
C20 Si2 C14 108.02(17) . . ?
C21 Si2 C14 106.5(2) . . ?
C19 C16 C17 111.6(2) . . ?
C19 C16 C15 123.6(3) . . ?
C17 C16 C15 124.8(2) . . ?
C15 C14 S4 109.8(2) . . ?
C15 C14 Si2 134.2(2) . . ?
S4 C14 Si2 116.01(15) . . ?
C6 C7 S1 111.8(2) . . ?
C6 C7 H7 124.1 . . ?
S1 C7 H7 124.1 . . ?
C7 C6 C5 111.3(2) . . ?
C7 C6 C17 124.0(2) . . ?
C5 C6 C17 124.6(2) . . ?
C14 C15 C12 112.8(2) . . ?
C14 C15 C16 123.9(2) . . ?
C12 C15 C16 123.2(2) . . ?
C12 C13 S4 112.1(2) . . ?
C12 C13 H13 124.0 . . ?
S4 C13 H13 124.0 . . ?
C8 C9 S2 112.5(2) . . ?
C8 C9 H9 123.8 . . ?
S2 C9 H9 123.8 . . ?
C11 C10 C8 111.6(3) . . ?
C11 C10 C12 123.7(3) . . ?
C8 C10 C12 124.5(2) . . ?
C18 C17 C16 111.6(2) . . ?
C18 C17 C6 123.9(3) . . ?
C16 C17 C6 124.5(2) . . ?
C9 C8 C10 111.7(3) . . ?
C9 C8 C5 123.6(3) . . ?
C10 C8 C5 124.5(2) . . ?
C16 C19 S3 112.5(2) . . ?
C16 C19 H19 123.8 . . ?
S3 C19 H19 123.8 . . ?
C5 C4 S1 109.3(2) . . ?
C5 C4 Si1 130.5(2) . . ?
S1 C4 Si1 119.90(16) . . ?
C4 C5 C6 114.0(2) . . ?
C4 C5 C8 122.5(2) . . ?
C6 C5 C8 123.4(2) . . ?
C13 C12 C15 112.0(3) . . ?
C13 C12 C10 122.8(2) . . ?
C15 C12 C10 125.2(2) . . ?
C10 C11 S2 112.6(2) . . ?
C10 C11 H11 123.7 . . ?
S2 C11 H11 123.7 . . ?
C17 C18 S3 112.7(2) . . ?
C17 C18 H18 123.7 . . ?
S3 C18 H18 123.7 . . ?
Si2 C22 H22A 109.5 . . ?
Si2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
Si2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Si1 C2 H2A 109.5 . . ?
Si1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
Si1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
Si2 C20 H20A 109.5 . . ?
Si2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
Si2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
Si1 C3 H3A 109.5 . . ?
Si1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
Si1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
Si2 C21 H21A 109.5 . . ?
Si2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
Si2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Si1 C1 H1A 109.5 . . ?
Si1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
Si1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1515999'
_audit_update_record             
;
2016-11-09 deposited with the CCDC.
2017-02-06 downloaded from the CCDC.
;
_audit_creation_date             2016-10-27
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H72 Li4 O4 S4 Si4'
_chemical_formula_sum            'C44 H72 Li4 O4 S4 Si4'
_chemical_formula_weight         933.37
_chemical_melting_point          ?
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'
Li Li -0.0003 0.0001 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   20.763(3)
_cell_length_b                   20.763(3)
_cell_length_c                   13.7545(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5929.5(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3029
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.97
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6459
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1171 before and 0.0452 after correction.
The Ratio of minimum to maximum transmission is 0.8662.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.046
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14919
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.776
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1558
_reflns_number_total             2608
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL-2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2608
_refine_ls_number_restraints     44
_refine_ls_R_factor_all          0.1222
_refine_ls_R_factor_gt           0.0831
_refine_ls_restrained_S_all      1.147
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1681P)²+7.1028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2424
_refine_ls_wR_factor_ref         0.2973
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C8-C9 = C9-C10 = C10-C11
 1.5 with sigma of 0.01
3. Rigid bond restraints
 C8, C9
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C9, C10
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C10, C11
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O1, C8
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O1, C11
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C9 \\sim C8 \\sim C10: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.02
O1 \\sim C8 \\sim C11: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.02
Si1 \\sim C6 \\sim C7: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
5.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
5.b Me refined with riding coordinates:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.59462(7) 0.36868(7) 0.01803(9) 0.0892(6) Uani 1 1 d . . . . .
Si1 Si 0.61597(9) 0.41401(9) 0.23650(11) 0.1102(7) Uani 1 1 d . U . . .
C1 C 0.5467(2) 0.3051(2) -0.0182(3) 0.0763(12) Uani 1 1 d . . . . .
C2 C 0.5217(2) 0.2777(2) 0.0675(3) 0.0702(11) Uani 1 1 d . . . . .
C3 C 0.5430(2) 0.3094(2) 0.1548(3) 0.0813(13) Uani 1 1 d . . . . .
H3 H 0.5303 0.2959 0.2164 0.098 Uiso 1 1 calc R . . . .
C4 C 0.5829(2) 0.3601(2) 0.1412(3) 0.0838(13) Uani 1 1 d . . . . .
C5 C 0.6868(3) 0.4593(4) 0.1911(5) 0.141(3) Uani 1 1 d . . . . .
H5A H 0.6743 0.4852 0.1365 0.212 Uiso 1 1 calc R . . . .
H5B H 0.7030 0.4866 0.2419 0.212 Uiso 1 1 calc R . . . .
H5C H 0.7197 0.4295 0.1716 0.212 Uiso 1 1 calc R . . . .
C6 C 0.5532(4) 0.4732(5) 0.2729(7) 0.185(4) Uani 1 1 d . U . . .
H6A H 0.5414 0.4989 0.2177 0.278 Uiso 1 1 calc R . . . .
H6B H 0.5160 0.4507 0.2966 0.278 Uiso 1 1 calc R . . . .
H6C H 0.5699 0.5006 0.3232 0.278 Uiso 1 1 calc R . . . .
C7 C 0.6389(6) 0.3652(5) 0.3394(6) 0.211(4) Uani 1 1 d . U . . .
H7A H 0.6020 0.3418 0.3625 0.316 Uiso 1 1 calc R . . . .
H7B H 0.6718 0.3353 0.3200 0.316 Uiso 1 1 calc R . . . .
H7C H 0.6551 0.3923 0.3903 0.316 Uiso 1 1 calc R . . . .
C8 C 0.5912(5) 0.4069(5) -0.3095(8) 0.191(3) Uani 1 1 d D U . . .
H8A H 0.5887 0.4499 -0.2823 0.229 Uiso 1 1 calc R . . . .
H8B H 0.5505 0.3965 -0.3403 0.229 Uiso 1 1 calc R . . . .
C9 C 0.6455(6) 0.4014(7) -0.3795(9) 0.238(4) Uani 1 1 d D U . . .
H9A H 0.6291 0.3830 -0.4394 0.285 Uiso 1 1 calc R . . . .
H9B H 0.6609 0.4444 -0.3942 0.285 Uiso 1 1 calc R . . . .
C10 C 0.6994(7) 0.3631(8) -0.3473(9) 0.255(5) Uani 1 1 d D U . . .
H10A H 0.7375 0.3889 -0.3350 0.305 Uiso 1 1 calc R . . . .
H10B H 0.7095 0.3285 -0.3921 0.305 Uiso 1 1 calc R . . . .
C11 C 0.6697(4) 0.3400(5) -0.2586(7) 0.178(3) Uani 1 1 d D U . . .
H11A H 0.6684 0.2934 -0.2609 0.213 Uiso 1 1 calc R . . . .
H11B H 0.6969 0.3521 -0.2043 0.213 Uiso 1 1 calc R . . . .
O1 O 0.6065(2) 0.3627(2) -0.2397(3) 0.1238(15) Uani 1 1 d . U . . .
Li1 Li 0.5465(4) 0.3057(4) -0.1783(5) 0.085(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.727(5) . ?
S1 C4 1.721(5) . ?
Si1 C4 1.856(5) . ?
Si1 C5 1.853(7) . ?
Si1 C6 1.859(9) . ?
Si1 C7 1.805(9) . ?
C1 C2 1.408(6) . ?
C1 Li1 2.203(8) . ?
C1 Li1 2.242(9) 11_665 ?
C1 Li1 2.257(10) 16_655 ?
C2 C2 1.462(9) 6_554 ?
C2 C3 1.439(6) . ?
C2 Li1 2.531(9) 16_655 ?
C2 Li1 2.557(9) 11_665 ?
C3 H3 0.9300 . ?
C3 C4 1.351(7) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.487(8) . ?
C8 O1 1.365(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.443(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.449(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 O1 1.417(10) . ?
O1 Li1 1.913(9) . ?
Li1 C1 2.257(10) 11_665 ?
Li1 C1 2.242(9) 16_655 ?
Li1 C2 2.531(9) 11_665 ?
Li1 C2 2.557(9) 16_655 ?
Li1 Li1 2.588(13) 11_665 ?
Li1 Li1 2.588(13) 16_655 ?
Li1 Li1 3.015(17) 6_554 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 S1 C1 97.1(2) . . ?
C4 Si1 C6 109.2(3) . . ?
C5 Si1 C4 111.2(3) . . ?
C5 Si1 C6 108.1(4) . . ?
C7 Si1 C4 108.2(4) . . ?
C7 Si1 C5 109.9(5) . . ?
C7 Si1 C6 110.2(6) . . ?
S1 C1 Li1 106.5(3) . . ?
S1 C1 Li1 140.0(3) . 11_665 ?
S1 C1 Li1 134.2(3) . 16_655 ?
C2 C1 S1 106.2(3) . . ?
C2 C1 Li1 147.1(4) . . ?
C2 C1 Li1 83.9(3) . 16_655 ?
C2 C1 Li1 85.7(3) . 11_665 ?
Li1 C1 Li1 71.2(3) . 11_665 ?
Li1 C1 Li1 84.1(4) 11_665 16_655 ?
Li1 C1 Li1 70.9(3) . 16_655 ?
C1 C2 C2 123.0(2) . 6_554 ?
C1 C2 C3 113.6(4) . . ?
C1 C2 Li1 62.5(3) . 16_655 ?
C1 C2 Li1 61.0(3) . 11_665 ?
C2 C2 Li1 74.3(3) 6_554 16_655 ?
C2 C2 Li1 72.3(3) 6_554 11_665 ?
C3 C2 C2 123.3(3) . 6_554 ?
C3 C2 Li1 139.1(4) . 16_655 ?
C3 C2 Li1 144.6(4) . 11_665 ?
Li1 C2 Li1 72.7(4) 16_655 11_665 ?
C2 C3 H3 122.3 . . ?
C4 C3 C2 115.4(4) . . ?
C4 C3 H3 122.3 . . ?
S1 C4 Si1 125.5(3) . . ?
C3 C4 S1 107.7(3) . . ?
C3 C4 Si1 126.8(4) . . ?
Si1 C5 H5A 109.5 . . ?
Si1 C5 H5B 109.5 . . ?
Si1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
Si1 C6 H6A 109.5 . . ?
Si1 C6 H6B 109.5 . . ?
Si1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
H8A C8 H8B 109.1 . . ?
C9 C8 H8A 111.1 . . ?
C9 C8 H8B 111.1 . . ?
O1 C8 H8A 111.1 . . ?
O1 C8 H8B 111.1 . . ?
O1 C8 C9 103.1(9) . . ?
C8 C9 H9A 108.4 . . ?
C8 C9 H9B 108.4 . . ?
H9A C9 H9B 107.5 . . ?
C10 C9 C8 115.6(11) . . ?
C10 C9 H9A 108.4 . . ?
C10 C9 H9B 108.4 . . ?
C9 C10 H10A 112.5 . . ?
C9 C10 H10B 112.5 . . ?
C9 C10 C11 96.3(10) . . ?
H10A C10 H10B 110.0 . . ?
C11 C10 H10A 112.5 . . ?
C11 C10 H10B 112.5 . . ?
C10 C11 H11A 108.3 . . ?
C10 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
O1 C11 C10 116.0(9) . . ?
O1 C11 H11A 108.3 . . ?
O1 C11 H11B 108.3 . . ?
C8 O1 C11 108.0(6) . . ?
C8 O1 Li1 125.0(6) . . ?
C11 O1 Li1 118.5(6) . . ?
C1 Li1 C1 83.6(3) 16_655 11_665 ?
C1 Li1 C1 108.7(4) . 11_665 ?
C1 Li1 C1 109.2(4) . 16_655 ?
C1 Li1 C2 138.8(4) . 11_665 ?
C1 Li1 C2 62.8(3) 11_665 16_655 ?
C1 Li1 C2 63.5(3) 16_655 11_665 ?
C1 Li1 C2 33.30(18) 16_655 16_655 ?
C1 Li1 C2 138.4(4) . 16_655 ?
C1 Li1 C2 33.59(18) 11_665 11_665 ?
C1 Li1 Li1 48.1(3) 16_655 6_554 ?
C1 Li1 Li1 89.8(2) . 6_554 ?
C1 Li1 Li1 47.7(3) 11_665 6_554 ?
C1 Li1 Li1 100.4(3) 11_665 16_655 ?
C1 Li1 Li1 55.5(3) . 16_655 ?
C1 Li1 Li1 53.7(2) 16_655 16_655 ?
C1 Li1 Li1 53.6(2) 11_665 11_665 ?
C1 Li1 Li1 100.8(3) 16_655 11_665 ?
C1 Li1 Li1 55.1(3) . 11_665 ?
C2 Li1 C2 33.4(2) 11_665 16_655 ?
C2 Li1 Li1 104.0(3) 16_655 11_665 ?
C2 Li1 Li1 104.8(3) 11_665 16_655 ?
C2 Li1 Li1 53.3(2) 16_655 6_554 ?
C2 Li1 Li1 85.3(3) 11_665 11_665 ?
C2 Li1 Li1 84.8(3) 16_655 16_655 ?
C2 Li1 Li1 54.1(2) 11_665 6_554 ?
O1 Li1 C1 112.8(4) . 11_665 ?
O1 Li1 C1 116.4(4) . . ?
O1 Li1 C1 121.3(4) . 16_655 ?
O1 Li1 C2 103.4(3) . 16_655 ?
O1 Li1 C2 99.2(3) . 11_665 ?
O1 Li1 Li1 135.2(5) . 11_665 ?
O1 Li1 Li1 146.0(5) . 16_655 ?
O1 Li1 Li1 153.1(3) . 6_554 ?
Li1 Li1 Li1 71.3(3) 11_665 16_655 ?
Li1 Li1 Li1 54.37(15) 11_665 6_554 ?
Li1 Li1 Li1 54.37(15) 16_655 6_554 ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

