# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2011



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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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. 
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#  fide research purposes only. It may contain copyright material 
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#  except for the purpose of generating routine backup copies 
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#  data retrieval see:
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data_masa442
_database_code_depnum_ccdc_archive 'CCDC 792994'
#TrackingRef '- TriphenylenoMe2SiloleWithCifCheck.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 Si'
_chemical_formula_sum            'C20 H16 Si'
_chemical_formula_weight         284.42

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           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

loop_
_symmetry_equiv_pos_as_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                   8.3831(10)
_cell_length_b                   11.7677(15)
_cell_length_c                   15.0120(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1480.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6063
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      27.91

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_process_details   
;
SADABS; Sheldrick 1996
;
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_number            10647
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         27.93
_reflns_number_total             3549
_reflns_number_gt                3356
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (Bruker 2000)'
_computing_cell_refinement       'Bruker SMART (Bruker 2000)'
_computing_data_reduction        'Bruker SAINT (Bruker 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0670P)^2^+0.1754P] where P=(Fo^2^+2Fc^2^)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(12)
_refine_ls_number_reflns         3549
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1005
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.08787(4) -0.06060(3) 0.49995(3) 0.02407(12) Uani 1 1 d . . .
C5 C 0.56533(16) 0.14336(13) 0.49803(11) 0.0275(3) Uani 1 1 d . . .
H5 H 0.6589 0.1856 0.5017 0.033 Uiso 1 1 calc R . .
C4 C 0.44845(18) 0.15291(13) 0.56562(10) 0.0234(3) Uani 1 1 d . . .
C9 C 0.30893(17) 0.08821(12) 0.55561(10) 0.0222(3) Uani 1 1 d . . .
C8 C 0.28512(17) 0.01264(13) 0.48384(9) 0.0233(3) Uani 1 1 d . . .
C10 C 0.17646(18) 0.09878(13) 0.61740(9) 0.0231(3) Uani 1 1 d . . .
C16 C 0.3327(2) 0.23756(13) 0.70401(10) 0.0263(3) Uani 1 1 d . . .
C11 C 0.04057(19) 0.03221(13) 0.59856(10) 0.0256(3) Uani 1 1 d . . .
C3 C 0.4628(2) 0.22658(13) 0.64434(10) 0.0260(3) Uani 1 1 d . . .
C13 C -0.0903(2) 0.12474(15) 0.72231(10) 0.0330(4) Uani 1 1 d . . .
H13 H -0.1807 0.1342 0.7575 0.040 Uiso 1 1 calc R . .
C6 C 0.5408(2) 0.07141(14) 0.42645(10) 0.0293(3) Uani 1 1 d . . .
H6 H 0.6178 0.0670 0.3820 0.035 Uiso 1 1 calc R . .
C7 C 0.4033(2) 0.00532(14) 0.41931(10) 0.0278(3) Uani 1 1 d . . .
H7 H 0.3907 -0.0437 0.3712 0.033 Uiso 1 1 calc R . .
C2 C 0.6047(2) 0.28594(14) 0.66251(12) 0.0317(3) Uani 1 1 d . . .
H2 H 0.6900 0.2798 0.6231 0.038 Uiso 1 1 calc R . .
C15 C 0.1836(2) 0.17602(13) 0.68865(10) 0.0255(3) Uani 1 1 d . . .
C14 C 0.0440(2) 0.18802(15) 0.74004(10) 0.0312(4) Uani 1 1 d . . .
H14 H 0.0426 0.2397 0.7869 0.037 Uiso 1 1 calc R . .
C12 C -0.0931(2) 0.04618(14) 0.65200(11) 0.0306(3) Uani 1 1 d . . .
H12 H -0.1845 0.0035 0.6412 0.037 Uiso 1 1 calc R . .
C18 C 0.4926(3) 0.36376(16) 0.79621(12) 0.0412(5) Uani 1 1 d . . .
H18 H 0.5025 0.4092 0.8466 0.049 Uiso 1 1 calc R . .
C1 C 0.6204(2) 0.35293(15) 0.73732(13) 0.0377(4) Uani 1 1 d . . .
H1 H 0.7158 0.3907 0.7485 0.045 Uiso 1 1 calc R . .
C17 C 0.3525(2) 0.30739(14) 0.77983(11) 0.0348(4) Uani 1 1 d . . .
H17 H 0.2682 0.3153 0.8197 0.042 Uiso 1 1 calc R . .
C20 C -0.05703(19) -0.05288(15) 0.40654(11) 0.0310(3) Uani 1 1 d . . .
H20A H -0.0153 -0.0932 0.3561 0.046 Uiso 1 1 calc R . .
H20B H -0.0745 0.0252 0.3907 0.046 Uiso 1 1 calc R . .
H20C H -0.1562 -0.0866 0.4246 0.046 Uiso 1 1 calc R . .
C19 C 0.1181(2) -0.21238(14) 0.53243(11) 0.0305(3) Uani 1 1 d . . .
H19A H 0.0168 -0.2466 0.5454 0.046 Uiso 1 1 calc R . .
H19B H 0.1849 -0.2160 0.5843 0.046 Uiso 1 1 calc R . .
H19C H 0.1683 -0.2525 0.4843 0.046 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Si1 0.0261(2) 0.0222(2) 0.0238(2) 0.00180(17) 0.00058(18) -0.00011(14)
C5 0.0239(7) 0.0260(7) 0.0325(7) 0.0067(7) 0.0019(7) 0.0008(5)
C4 0.0259(7) 0.0212(7) 0.0231(7) 0.0051(5) -0.0013(6) 0.0035(5)
C9 0.0244(7) 0.0212(7) 0.0209(6) 0.0045(5) 0.0005(5) 0.0043(5)
C8 0.0241(6) 0.0237(7) 0.0222(7) 0.0027(5) 0.0016(6) 0.0025(5)
C10 0.0273(7) 0.0225(7) 0.0195(7) 0.0053(5) 0.0019(5) 0.0053(6)
C16 0.0369(8) 0.0225(7) 0.0196(7) 0.0023(5) -0.0034(6) 0.0070(6)
C11 0.0288(7) 0.0247(7) 0.0232(7) 0.0052(5) 0.0042(6) 0.0038(6)
C3 0.0329(8) 0.0214(7) 0.0237(7) 0.0042(6) -0.0050(6) 0.0044(6)
C13 0.0350(8) 0.0394(9) 0.0247(7) 0.0101(6) 0.0117(7) 0.0126(7)
C6 0.0285(7) 0.0319(8) 0.0274(7) 0.0047(6) 0.0083(6) 0.0062(6)
C7 0.0328(8) 0.0271(7) 0.0236(7) -0.0006(6) 0.0029(6) 0.0057(6)
C2 0.0364(8) 0.0249(7) 0.0338(8) 0.0055(6) -0.0082(7) 0.0022(7)
C15 0.0337(8) 0.0244(7) 0.0183(6) 0.0052(5) 0.0010(6) 0.0063(6)
C14 0.0425(9) 0.0329(8) 0.0184(7) 0.0041(6) 0.0048(7) 0.0134(7)
C12 0.0282(7) 0.0308(8) 0.0329(8) 0.0104(6) 0.0058(6) 0.0017(7)
C18 0.0639(13) 0.0282(9) 0.0315(9) -0.0051(7) -0.0161(9) 0.0058(9)
C1 0.0454(10) 0.0256(8) 0.0422(10) 0.0037(7) -0.0185(8) -0.0018(7)
C17 0.0526(10) 0.0269(8) 0.0248(8) -0.0026(6) -0.0043(7) 0.0075(8)
C20 0.0306(8) 0.0293(8) 0.0331(8) 0.0055(7) -0.0035(6) -0.0028(7)
C19 0.0399(9) 0.0251(7) 0.0265(7) 0.0018(6) -0.0006(6) 0.0017(7)

_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 C20 1.8574(17) . ?
Si1 C19 1.8687(16) . ?
Si1 C8 1.8803(15) . ?
Si1 C11 1.8819(17) . ?
C5 C6 1.384(2) . ?
C5 C4 1.415(2) . ?
C5 H5 0.9300 . ?
C4 C9 1.404(2) . ?
C4 C3 1.471(2) . ?
C9 C8 1.411(2) . ?
C9 C10 1.4523(19) . ?
C8 C7 1.388(2) . ?
C10 C15 1.405(2) . ?
C10 C11 1.411(2) . ?
C16 C17 1.414(2) . ?
C16 C3 1.417(2) . ?
C16 C15 1.463(2) . ?
C11 C12 1.388(2) . ?
C3 C2 1.406(2) . ?
C13 C14 1.376(3) . ?
C13 C12 1.403(2) . ?
C13 H13 0.9300 . ?
C6 C7 1.395(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C2 C1 1.378(3) . ?
C2 H2 0.9300 . ?
C15 C14 1.409(2) . ?
C14 H14 0.9300 . ?
C12 H12 0.9300 . ?
C18 C17 1.372(3) . ?
C18 C1 1.395(3) . ?
C18 H18 0.9300 . ?
C1 H1 0.9300 . ?
C17 H17 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C20 Si1 C19 109.42(8) . . ?
C20 Si1 C8 117.11(7) . . ?
C19 Si1 C8 110.62(7) . . ?
C20 Si1 C11 115.32(7) . . ?
C19 Si1 C11 112.21(7) . . ?
C8 Si1 C11 91.17(7) . . ?
C6 C5 C4 120.16(14) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C9 C4 C5 117.21(14) . . ?
C9 C4 C3 118.29(13) . . ?
C5 C4 C3 124.50(14) . . ?
C4 C9 C8 122.78(13) . . ?
C4 C9 C10 121.49(13) . . ?
C8 C9 C10 115.69(13) . . ?
C7 C8 C9 118.10(14) . . ?
C7 C8 Si1 133.53(12) . . ?
C9 C8 Si1 108.36(10) . . ?
C15 C10 C11 123.11(14) . . ?
C15 C10 C9 120.60(14) . . ?
C11 C10 C9 116.21(13) . . ?
C17 C16 C3 118.14(16) . . ?
C17 C16 C15 121.00(16) . . ?
C3 C16 C15 120.84(14) . . ?
C12 C11 C10 118.05(15) . . ?
C12 C11 Si1 133.91(13) . . ?
C10 C11 Si1 108.04(11) . . ?
C2 C3 C16 118.89(15) . . ?
C2 C3 C4 121.19(15) . . ?
C16 C3 C4 119.92(14) . . ?
C14 C13 C12 121.05(15) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C5 C6 C7 121.60(14) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 120.10(14) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C1 C2 C3 121.53(18) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C10 C15 C14 116.51(15) . . ?
C10 C15 C16 118.48(14) . . ?
C14 C15 C16 125.01(15) . . ?
C13 C14 C15 121.31(15) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C11 C12 C13 119.94(16) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C17 C18 C1 120.01(16) . . ?
C17 C18 H18 120.0 . . ?
C1 C18 H18 120.0 . . ?
C2 C1 C18 119.68(18) . . ?
C2 C1 H1 120.2 . . ?
C18 C1 H1 120.2 . . ?
C18 C17 C16 121.74(18) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
Si1 C20 H20A 109.5 . . ?
Si1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
Si1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
Si1 C19 H19A 109.5 . . ?
Si1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
Si1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.93
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.059