# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mo_20101028a_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H19 Si'
_chemical_formula_weight         239.40

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'
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                   8.6845(10)
_cell_length_b                   10.2120(12)
_cell_length_c                   15.7233(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.264(2)
_cell_angle_gamma                90.00
_cell_volume                     1386.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5685
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.949
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_process_details   ?

_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            9670
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2424
_reflns_number_gt                2145
_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)+(0.0720P)²+1.0396P] 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         2424
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1485
_refine_ls_wR_factor_gt          0.1284
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_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 0.47747(7) 0.05477(5) 0.06515(4) 0.0316(2) Uani 1 1 d . . .
C7 C 0.6705(3) 0.1024(2) 0.12683(14) 0.0371(5) Uani 1 1 d . . .
C1 C 0.3698(3) 0.2137(2) 0.03998(14) 0.0379(5) Uani 1 1 d . . .
C12 C 0.7477(3) 0.2141(3) 0.10382(16) 0.0473(6) Uani 1 1 d . . .
H12 H 0.7034 0.2642 0.0582 0.057 Uiso 1 1 calc R . .
C8 C 0.7433(3) 0.0313(2) 0.19546(16) 0.0459(6) Uani 1 1 d . . .
H8 H 0.6970 -0.0449 0.2128 0.055 Uiso 1 1 calc R . .
C9 C 0.8831(3) 0.0717(3) 0.23838(18) 0.0542(7) Uani 1 1 d . . .
H9 H 0.9291 0.0222 0.2839 0.065 Uiso 1 1 calc R . .
C10 C 0.9542(3) 0.1827(3) 0.21499(18) 0.0549(7) Uani 1 1 d . . .
H10 H 1.0465 0.2101 0.2453 0.066 Uiso 1 1 calc R . .
C2 C 0.3986(3) 0.3239(2) 0.09122(17) 0.0498(7) Uani 1 1 d . . .
H2 H 0.4746 0.3198 0.1377 0.060 Uiso 1 1 calc R . .
C3 C 0.3179(4) 0.4393(3) 0.0752(2) 0.0622(8) Uani 1 1 d . . .
H3 H 0.3404 0.5115 0.1104 0.075 Uiso 1 1 calc R . .
C11 C 0.8890(3) 0.2537(3) 0.14660(18) 0.0549(7) Uani 1 1 d . . .
H11 H 0.9387 0.3279 0.1288 0.066 Uiso 1 1 calc R . .
C4 C 0.2048(4) 0.4477(3) 0.0077(2) 0.0626(8) Uani 1 1 d . . .
H4 H 0.1515 0.5259 -0.0036 0.075 Uiso 1 1 calc R . .
C6 C 0.2530(3) 0.2244(3) -0.02681(17) 0.0528(7) Uani 1 1 d . . .
H6 H 0.2291 0.1523 -0.0619 0.063 Uiso 1 1 calc R . .
C5 C 0.1702(4) 0.3402(3) -0.04316(19) 0.0663(9) Uani 1 1 d . . .
H5 H 0.0918 0.3446 -0.0884 0.080 Uiso 1 1 calc R . .
C16 C 0.3519(3) -0.0457(2) 0.13488(15) 0.0398(6) Uani 1 1 d . . .
C15 C 0.1837(3) -0.0506(3) 0.09336(19) 0.0553(7) Uani 1 1 d . . .
H15A H 0.1222 -0.0999 0.1291 0.083 Uiso 1 1 calc R . .
H15B H 0.1802 -0.0917 0.0383 0.083 Uiso 1 1 calc R . .
H15C H 0.1436 0.0369 0.0867 0.083 Uiso 1 1 calc R . .
C13 C 0.3527(3) 0.0233(3) 0.22237(16) 0.0526(7) Uani 1 1 d . . .
H13A H 0.3209 0.1127 0.2136 0.079 Uiso 1 1 calc R . .
H13B H 0.4553 0.0206 0.2520 0.079 Uiso 1 1 calc R . .
H13C H 0.2823 -0.0207 0.2558 0.079 Uiso 1 1 calc R . .
C14 C 0.4112(4) -0.1873(2) 0.14917(18) 0.0547(7) Uani 1 1 d . . .
H14A H 0.5167 -0.1857 0.1748 0.082 Uiso 1 1 calc R . .
H14B H 0.4055 -0.2321 0.0952 0.082 Uiso 1 1 calc R . .
H14C H 0.3482 -0.2322 0.1864 0.082 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 C1 1.893(2) . ?
Si1 C7 1.906(2) . ?
Si1 C16 1.924(2) . ?
Si1 Si1 2.4036(11) 3_655 ?
C7 C12 1.391(3) . ?
C7 C8 1.394(3) . ?
C1 C6 1.382(3) . ?
C1 C2 1.392(3) . ?
C12 C11 1.394(4) . ?
C12 H12 0.9300 . ?
C8 C9 1.386(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.360(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.367(4) . ?
C10 H10 0.9300 . ?
C2 C3 1.380(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(5) . ?
C3 H3 0.9300 . ?
C11 H11 0.9300 . ?
C4 C5 1.372(4) . ?
C4 H4 0.9300 . ?
C6 C5 1.393(4) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
C16 C15 1.534(4) . ?
C16 C14 1.543(3) . ?
C16 C13 1.545(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C1 Si1 C7 105.93(10) . . ?
C1 Si1 C16 106.16(10) . . ?
C7 Si1 C16 111.58(11) . . ?
C1 Si1 Si1 110.08(8) . 3_655 ?
C7 Si1 Si1 109.67(8) . 3_655 ?
C16 Si1 Si1 113.11(8) . 3_655 ?
C12 C7 C8 116.0(2) . . ?
C12 C7 Si1 119.95(17) . . ?
C8 C7 Si1 124.06(19) . . ?
C6 C1 C2 116.5(2) . . ?
C6 C1 Si1 122.13(18) . . ?
C2 C1 Si1 121.28(18) . . ?
C7 C12 C11 122.5(2) . . ?
C7 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C9 C8 C7 121.4(3) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C10 C9 C8 121.1(3) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 119.5(2) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C3 C2 C1 122.0(2) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C10 C11 C12 119.5(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C3 C4 C5 119.7(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C1 C6 C5 121.9(2) . . ?
C1 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C15 C16 C14 108.6(2) . . ?
C15 C16 C13 107.8(2) . . ?
C14 C16 C13 109.2(2) . . ?
C15 C16 Si1 110.32(17) . . ?
C14 C16 Si1 112.45(17) . . ?
C13 C16 Si1 108.47(17) . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16 C13 H13A 109.5 . . ?
C16 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C16 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C16 C14 H14A 109.5 . . ?
C16 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C16 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 Si1 C7 C12 -38.4(2) . . . . ?
C16 Si1 C7 C12 -153.47(19) . . . . ?
Si1 Si1 C7 C12 80.4(2) 3_655 . . . ?
C1 Si1 C7 C8 141.9(2) . . . . ?
C16 Si1 C7 C8 26.8(2) . . . . ?
Si1 Si1 C7 C8 -99.3(2) 3_655 . . . ?
C7 Si1 C1 C6 157.4(2) . . . . ?
C16 Si1 C1 C6 -83.9(2) . . . . ?
Si1 Si1 C1 C6 38.9(2) 3_655 . . . ?
C7 Si1 C1 C2 -26.3(2) . . . . ?
C16 Si1 C1 C2 92.4(2) . . . . ?
Si1 Si1 C1 C2 -144.8(2) 3_655 . . . ?
C8 C7 C12 C11 -0.3(4) . . . . ?
Si1 C7 C12 C11 180.0(2) . . . . ?
C12 C7 C8 C9 0.9(4) . . . . ?
Si1 C7 C8 C9 -179.4(2) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C8 C9 C10 C11 -1.8(4) . . . . ?
C6 C1 C2 C3 -1.6(4) . . . . ?
Si1 C1 C2 C3 -178.0(2) . . . . ?
C1 C2 C3 C4 0.5(5) . . . . ?
C9 C10 C11 C12 2.4(4) . . . . ?
C7 C12 C11 C10 -1.4(4) . . . . ?
C2 C3 C4 C5 1.1(5) . . . . ?
C2 C1 C6 C5 1.1(4) . . . . ?
Si1 C1 C6 C5 177.6(2) . . . . ?
C3 C4 C5 C6 -1.5(5) . . . . ?
C1 C6 C5 C4 0.3(5) . . . . ?
C1 Si1 C16 C15 49.63(19) . . . . ?
C7 Si1 C16 C15 164.59(17) . . . . ?
Si1 Si1 C16 C15 -71.19(18) 3_655 . . . ?
C1 Si1 C16 C14 170.97(18) . . . . ?
C7 Si1 C16 C14 -74.1(2) . . . . ?
Si1 Si1 C16 C14 50.2(2) 3_655 . . . ?
C1 Si1 C16 C13 -68.18(19) . . . . ?
C7 Si1 C16 C13 46.8(2) . . . . ?
Si1 Si1 C16 C13 171.00(15) 3_655 . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 1009555'
