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

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#
#                 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
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_4ab

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H36 Si2'
_chemical_formula_weight         500.81

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           Triclinic
_symmetry_space_group_name_H-M   'P-1   '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8603(13)
_cell_length_b                   10.5873(14)
_cell_length_c                   14.4723(19)
_cell_angle_alpha                72.748(2)
_cell_angle_beta                 86.325(2)
_cell_angle_gamma                84.298(2)
_cell_volume                     1434.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    123
_cell_measurement_reflns_used    2599
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      27.44
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9581
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            8189
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_sigmaI/netI    0.0457
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         27.49
_reflns_number_total             6222
_reflns_number_gt                4742
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_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)+(0.0100P)²+1.0000P] 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         6222
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.0863
_refine_ls_wR_factor_gt          0.0789
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
C1 C 0.2981(2) 0.42369(18) 0.14520(15) 0.0301(5) Uani 1 1 d . . .
H1A H 0.2918 0.5181 0.1061 0.036 Uiso 1 1 calc R . .
H1B H 0.3750 0.4084 0.1891 0.036 Uiso 1 1 calc R . .
C2A C -0.0176(2) 0.44418(19) 0.14335(15) 0.0307(5) Uani 1 1 d . . .
H2A1 H -0.0251 0.5414 0.1202 0.046 Uiso 1 1 calc R . .
H2A2 H -0.0993 0.4140 0.1828 0.046 Uiso 1 1 calc R . .
H2A3 H -0.0091 0.4084 0.0879 0.046 Uiso 1 1 calc R . .
C2B C 0.1209(2) 0.4528(2) 0.32366(15) 0.0362(5) Uani 1 1 d . . .
H2B1 H 0.2031 0.4232 0.3616 0.054 Uiso 1 1 calc R . .
H2B2 H 0.0409 0.4208 0.3644 0.054 Uiso 1 1 calc R . .
H2B3 H 0.1112 0.5500 0.3005 0.054 Uiso 1 1 calc R . .
C3 C 0.16880(18) 0.20068(17) 0.26242(13) 0.0218(4) Uani 1 1 d . . .
H3 H 0.1239 0.1532 0.3206 0.026 Uiso 1 1 calc R . .
C4 C 0.25488(17) 0.13338(17) 0.21423(12) 0.0182(4) Uani 1 1 d . . .
C5 C 0.33480(17) 0.12178(18) 0.04954(13) 0.0222(4) Uani 1 1 d . . .
H5 H 0.3271 0.0288 0.0726 0.027 Uiso 1 1 calc R . .
C6 C 0.37171(19) 0.1784(2) -0.04692(13) 0.0282(4) Uani 1 1 d . . .
H6 H 0.3890 0.1246 -0.0893 0.034 Uiso 1 1 calc R . .
C7 C 0.38316(19) 0.3137(2) -0.08109(14) 0.0320(5) Uani 1 1 d . . .
H7 H 0.4068 0.3538 -0.1473 0.038 Uiso 1 1 calc R . .
C8 C 0.35998(19) 0.3903(2) -0.01824(14) 0.0312(5) Uani 1 1 d . . .
H8 H 0.3693 0.4830 -0.0421 0.037 Uiso 1 1 calc R . .
C9 C 0.32333(18) 0.33578(18) 0.07923(14) 0.0240(4) Uani 1 1 d . . .
C10 C 0.30856(17) 0.19788(17) 0.11386(12) 0.0194(4) Uani 1 1 d . . .
C11 C 0.29598(18) -0.01063(16) 0.25887(12) 0.0180(4) Uani 1 1 d . . .
C12 C 0.19965(18) -0.09789(17) 0.30702(12) 0.0202(4) Uani 1 1 d . . .
H12 H 0.1062 -0.0663 0.3088 0.024 Uiso 1 1 calc R . .
C13 C 0.23898(19) -0.23047(18) 0.35234(13) 0.0238(4) Uani 1 1 d . . .
H13 H 0.1723 -0.2889 0.3847 0.029 Uiso 1 1 calc R . .
C14 C 0.3749(2) -0.27800(18) 0.35063(13) 0.0263(4) Uani 1 1 d . . .
H14 H 0.4015 -0.3688 0.3815 0.032 Uiso 1 1 calc R . .
C15 C 0.47197(19) -0.19240(18) 0.30366(13) 0.0267(4) Uani 1 1 d . . .
H15 H 0.5654 -0.2243 0.3030 0.032 Uiso 1 1 calc R . .
C16 C 0.43265(18) -0.05988(18) 0.25750(13) 0.0221(4) Uani 1 1 d . . .
H16 H 0.4996 -0.0021 0.2246 0.027 Uiso 1 1 calc R . .
C17 C 0.7959(2) 0.1138(2) 0.41614(14) 0.0322(5) Uani 1 1 d . . .
H17A H 0.8805 0.1603 0.4033 0.039 Uiso 1 1 calc R . .
H17B H 0.7796 0.0818 0.4872 0.039 Uiso 1 1 calc R . .
C18A C 0.6659(3) 0.4034(2) 0.37012(16) 0.0469(6) Uani 1 1 d . . .
H18A H 0.5949 0.4656 0.3329 0.070 Uiso 1 1 calc R . .
H18B H 0.7559 0.4315 0.3442 0.070 Uiso 1 1 calc R . .
H18C H 0.6557 0.4023 0.4382 0.070 Uiso 1 1 calc R . .
C18B C 0.4815(2) 0.1762(2) 0.41370(14) 0.0355(5) Uani 1 1 d . . .
H18D H 0.4082 0.2377 0.3788 0.053 Uiso 1 1 calc R . .
H18E H 0.4744 0.1732 0.4822 0.053 Uiso 1 1 calc R . .
H18F H 0.4734 0.0873 0.4080 0.053 Uiso 1 1 calc R . .
C19 C 0.68003(19) 0.23818(18) 0.23192(13) 0.0242(4) Uani 1 1 d . . .
H19 H 0.6394 0.3107 0.1831 0.029 Uiso 1 1 calc R . .
C20 C 0.75802(17) 0.14205(17) 0.20540(12) 0.0195(4) Uani 1 1 d . . .
C21 C 0.82512(17) -0.09998(18) 0.24352(13) 0.0219(4) Uani 1 1 d . . .
H21 H 0.8195 -0.0897 0.1764 0.026 Uiso 1 1 calc R . .
C22 C 0.85516(19) -0.22600(19) 0.30611(14) 0.0275(4) Uani 1 1 d . . .
H22 H 0.8691 -0.3008 0.2821 0.033 Uiso 1 1 calc R . .
C23 C 0.8645(2) -0.2415(2) 0.40374(15) 0.0341(5) Uani 1 1 d . . .
H23 H 0.8842 -0.3272 0.4475 0.041 Uiso 1 1 calc R . .
C24 C 0.8451(2) -0.1313(2) 0.43741(14) 0.0331(5) Uani 1 1 d . . .
H24 H 0.8528 -0.1430 0.5046 0.040 Uiso 1 1 calc R . .
C25 C 0.81459(18) -0.00345(19) 0.37608(13) 0.0252(4) Uani 1 1 d . . .
C26 C 0.80287(17) 0.01233(17) 0.27636(12) 0.0195(4) Uani 1 1 d . . .
C27 C 0.79969(18) 0.15955(16) 0.10132(12) 0.0179(4) Uani 1 1 d . . .
C28 C 0.70301(18) 0.19449(17) 0.02968(12) 0.0203(4) Uani 1 1 d . . .
H28 H 0.6089 0.2052 0.0470 0.024 Uiso 1 1 calc R . .
C29 C 0.74377(19) 0.21366(17) -0.06708(13) 0.0213(4) Uani 1 1 d . . .
H29 H 0.6772 0.2354 -0.1152 0.026 Uiso 1 1 calc R . .
C30 C 0.88044(19) 0.20118(17) -0.09344(13) 0.0225(4) Uani 1 1 d . . .
H30 H 0.9080 0.2147 -0.1595 0.027 Uiso 1 1 calc R . .
C31 C 0.97748(19) 0.16878(18) -0.02276(13) 0.0234(4) Uani 1 1 d . . .
H31 H 1.0717 0.1622 -0.0408 0.028 Uiso 1 1 calc R . .
C32 C 0.93731(18) 0.14602(17) 0.07375(13) 0.0214(4) Uani 1 1 d . . .
H32 H 1.0042 0.1209 0.1218 0.026 Uiso 1 1 calc R . .
Si1 Si 0.13565(5) 0.38478(5) 0.21786(4) 0.02349(12) Uani 1 1 d . . .
Si2 Si 0.64927(6) 0.23360(5) 0.36089(4) 0.02569(13) 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
C1 C9 1.513(3) . ?
C1 Si1 1.871(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2A Si1 1.860(2) . ?
C2A H2A1 0.9800 . ?
C2A H2A2 0.9800 . ?
C2A H2A3 0.9800 . ?
C2B Si1 1.868(2) . ?
C2B H2B1 0.9800 . ?
C2B H2B2 0.9800 . ?
C2B H2B3 0.9800 . ?
C3 C4 1.347(2) . ?
C3 Si1 1.8646(18) . ?
C3 H3 0.9500 . ?
C4 C11 1.494(2) . ?
C4 C10 1.497(2) . ?
C5 C6 1.386(3) . ?
C5 C10 1.398(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.395(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.415(2) . ?
C11 C12 1.396(2) . ?
C11 C16 1.397(2) . ?
C12 C13 1.389(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C25 1.510(3) . ?
C17 Si2 1.876(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18A Si2 1.866(2) . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C18B Si2 1.858(2) . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 0.9800 . ?
C19 C20 1.346(2) . ?
C19 Si2 1.8587(19) . ?
C19 H19 0.9500 . ?
C20 C26 1.496(2) . ?
C20 C27 1.498(2) . ?
C21 C22 1.388(2) . ?
C21 C26 1.399(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.381(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.397(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.414(2) . ?
C27 C32 1.395(2) . ?
C27 C28 1.396(2) . ?
C28 C29 1.393(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.381(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.390(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.383(2) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?

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
C9 C1 Si1 109.37(13) . . ?
C9 C1 H1A 109.8 . . ?
Si1 C1 H1A 109.8 . . ?
C9 C1 H1B 109.8 . . ?
Si1 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
Si1 C2A H2A1 109.5 . . ?
Si1 C2A H2A2 109.5 . . ?
H2A1 C2A H2A2 109.5 . . ?
Si1 C2A H2A3 109.5 . . ?
H2A1 C2A H2A3 109.5 . . ?
H2A2 C2A H2A3 109.5 . . ?
Si1 C2B H2B1 109.5 . . ?
Si1 C2B H2B2 109.5 . . ?
H2B1 C2B H2B2 109.5 . . ?
Si1 C2B H2B3 109.5 . . ?
H2B1 C2B H2B3 109.5 . . ?
H2B2 C2B H2B3 109.5 . . ?
C4 C3 Si1 121.62(14) . . ?
C4 C3 H3 119.2 . . ?
Si1 C3 H3 119.2 . . ?
C3 C4 C11 120.40(16) . . ?
C3 C4 C10 121.69(16) . . ?
C11 C4 C10 117.88(15) . . ?
C6 C5 C10 121.77(18) . . ?
C6 C5 H5 119.1 . . ?
C10 C5 H5 119.1 . . ?
C7 C6 C5 119.52(18) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C8 C7 C6 119.58(18) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 122.02(18) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
C8 C9 C10 118.50(18) . . ?
C8 C9 C1 120.16(17) . . ?
C10 C9 C1 121.33(17) . . ?
C5 C10 C9 118.58(17) . . ?
C5 C10 C4 119.07(16) . . ?
C9 C10 C4 122.16(16) . . ?
C12 C11 C16 118.40(16) . . ?
C12 C11 C4 120.77(15) . . ?
C16 C11 C4 120.76(16) . . ?
C13 C12 C11 120.70(17) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C12 120.33(18) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.67(17) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 120.09(17) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 120.81(17) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C25 C17 Si2 111.88(13) . . ?
C25 C17 H17A 109.2 . . ?
Si2 C17 H17A 109.2 . . ?
C25 C17 H17B 109.2 . . ?
Si2 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
Si2 C18A H18A 109.5 . . ?
Si2 C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
Si2 C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
Si2 C18B H18D 109.5 . . ?
Si2 C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
Si2 C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C20 C19 Si2 122.15(14) . . ?
C20 C19 H19 118.9 . . ?
Si2 C19 H19 118.9 . . ?
C19 C20 C26 122.44(16) . . ?
C19 C20 C27 120.63(16) . . ?
C26 C20 C27 116.90(15) . . ?
C22 C21 C26 122.00(17) . . ?
C22 C21 H21 119.0 . . ?
C26 C21 H21 119.0 . . ?
C23 C22 C21 119.27(19) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C22 C23 C24 119.60(18) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C23 C24 C25 122.31(18) . . ?
C23 C24 H24 118.8 . . ?
C25 C24 H24 118.8 . . ?
C24 C25 C26 118.18(18) . . ?
C24 C25 C17 120.33(17) . . ?
C26 C25 C17 121.49(17) . . ?
C21 C26 C25 118.63(16) . . ?
C21 C26 C20 118.30(15) . . ?
C25 C26 C20 122.93(16) . . ?
C32 C27 C28 118.68(16) . . ?
C32 C27 C20 120.22(15) . . ?
C28 C27 C20 121.05(16) . . ?
C29 C28 C27 120.34(16) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C30 C29 C28 120.36(16) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C29 C30 C31 119.65(16) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 H30 120.2 . . ?
C32 C31 C30 120.21(17) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C31 C32 C27 120.72(16) . . ?
C31 C32 H32 119.6 . . ?
C27 C32 H32 119.6 . . ?
C2A Si1 C3 114.60(9) . . ?
C2A Si1 C2B 109.85(9) . . ?
C3 Si1 C2B 108.99(9) . . ?
C2A Si1 C1 112.40(10) . . ?
C3 Si1 C1 98.63(8) . . ?
C2B Si1 C1 111.97(10) . . ?
C18B Si2 C19 114.35(9) . . ?
C18B Si2 C18A 110.10(11) . . ?
C19 Si2 C18A 107.94(9) . . ?
C18B Si2 C17 112.49(10) . . ?
C19 Si2 C17 99.75(8) . . ?
C18A Si2 C17 111.82(11) . . ?

_diffrn_measured_fraction_theta_max 0.944
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.944
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 989789'
#######################################################################
#
#                 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_4ae

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 Si'
_chemical_formula_weight         312.47

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'
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)/n  '
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                   9.7459(10)
_cell_length_b                   10.4452(11)
_cell_length_c                   18.2147(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.6900(10)
_cell_angle_gamma                90.00
_cell_volume                     1827.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123
_cell_measurement_reflns_used    5728
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      27.49
_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9752
_exptl_absorpt_correction_T_max  0.9814
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            10169
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         27.52
_reflns_number_total             4132
_reflns_number_gt                3607
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_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)+(0.0100P)²+1.3000P] 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         4132
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0764
_refine_ls_wR_factor_gt          0.0729
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
C1 C 0.43492(13) 0.35126(12) 0.02532(7) 0.0203(3) Uani 1 1 d . . .
H1A H 0.4426 0.4227 0.0615 0.024 Uiso 1 1 calc R . .
H1B H 0.4230 0.3882 -0.0254 0.024 Uiso 1 1 calc R . .
C2A C 0.75512(13) 0.35565(13) 0.06222(8) 0.0247(3) Uani 1 1 d . . .
H2A1 H 0.7617 0.4084 0.0185 0.037 Uiso 1 1 calc R . .
H2A2 H 0.8380 0.3014 0.0736 0.037 Uiso 1 1 calc R . .
H2A3 H 0.7489 0.4112 0.1049 0.037 Uiso 1 1 calc R . .
C2B C 0.60825(16) 0.14347(14) -0.03701(8) 0.0289(3) Uani 1 1 d . . .
H2B1 H 0.6173 0.1941 -0.0813 0.043 Uiso 1 1 calc R . .
H2B2 H 0.5237 0.0912 -0.0472 0.043 Uiso 1 1 calc R . .
H2B3 H 0.6896 0.0876 -0.0244 0.043 Uiso 1 1 calc R . .
C3 C 0.57227(13) 0.16601(12) 0.12966(7) 0.0177(2) Uani 1 1 d . . .
C4 C 0.44321(13) 0.15332(11) 0.14697(7) 0.0175(2) Uani 1 1 d . . .
C5 C 0.19012(13) 0.11921(12) 0.10037(7) 0.0204(3) Uani 1 1 d . . .
H5 H 0.1895 0.0640 0.1417 0.024 Uiso 1 1 calc R . .
C6 C 0.06947(13) 0.13332(13) 0.04852(7) 0.0233(3) Uani 1 1 d . . .
H6 H -0.0126 0.0884 0.0547 0.028 Uiso 1 1 calc R . .
C7 C 0.06871(14) 0.21303(13) -0.01234(8) 0.0247(3) Uani 1 1 d . . .
H7 H -0.0127 0.2210 -0.0489 0.030 Uiso 1 1 calc R . .
C8 C 0.18819(14) 0.28125(13) -0.01940(7) 0.0224(3) Uani 1 1 d . . .
H8 H 0.1870 0.3368 -0.0608 0.027 Uiso 1 1 calc R . .
C9 C 0.30999(13) 0.27015(12) 0.03288(7) 0.0181(2) Uani 1 1 d . . .
C10 C 0.31315(13) 0.18449(12) 0.09332(7) 0.0172(2) Uani 1 1 d . . .
C11 C 0.70090(13) 0.12158(12) 0.17960(7) 0.0208(3) Uani 1 1 d . . .
C12 C 0.78361(14) 0.02702(14) 0.15466(8) 0.0277(3) Uani 1 1 d . . .
H12 H 0.7551 -0.0106 0.1070 0.033 Uiso 1 1 calc R . .
C13 C 0.90680(15) -0.01269(17) 0.19852(10) 0.0380(4) Uani 1 1 d . . .
H13 H 0.9612 -0.0778 0.1810 0.046 Uiso 1 1 calc R . .
C14 C 0.95044(16) 0.04198(18) 0.26732(10) 0.0432(4) Uani 1 1 d . . .
H14 H 1.0350 0.0151 0.2972 0.052 Uiso 1 1 calc R . .
C15 C 0.87034(17) 0.13641(18) 0.29268(9) 0.0417(4) Uani 1 1 d . . .
H15 H 0.9004 0.1743 0.3401 0.050 Uiso 1 1 calc R . .
C16 C 0.74597(16) 0.17638(15) 0.24930(8) 0.0307(3) Uani 1 1 d . . .
H16 H 0.6918 0.2412 0.2673 0.037 Uiso 1 1 calc R . .
C17 C 0.42081(13) 0.09429(13) 0.21923(7) 0.0206(3) Uani 1 1 d . . .
C18 C 0.46283(14) -0.03116(14) 0.23736(8) 0.0257(3) Uani 1 1 d . . .
H18 H 0.5081 -0.0792 0.2041 0.031 Uiso 1 1 calc R . .
C19 C 0.43914(16) -0.08651(16) 0.30343(8) 0.0345(4) Uani 1 1 d . . .
H19 H 0.4668 -0.1725 0.3147 0.041 Uiso 1 1 calc R . .
C20 C 0.37567(16) -0.01711(18) 0.35273(8) 0.0399(4) Uani 1 1 d . . .
H20 H 0.3608 -0.0546 0.3983 0.048 Uiso 1 1 calc R . .
C21 C 0.33357(15) 0.10783(18) 0.33551(8) 0.0362(4) Uani 1 1 d . . .
H21 H 0.2898 0.1557 0.3694 0.043 Uiso 1 1 calc R . .
C22 C 0.35500(14) 0.16361(15) 0.26873(7) 0.0268(3) Uani 1 1 d . . .
H22 H 0.3248 0.2488 0.2570 0.032 Uiso 1 1 calc R . .
Si1 Si 0.59719(4) 0.25310(3) 0.042610(19) 0.01736(8) 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
C1 C9 1.5085(17) . ?
C1 Si1 1.8665(13) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2A Si1 1.8598(13) . ?
C2A H2A1 0.9800 . ?
C2A H2A2 0.9800 . ?
C2A H2A3 0.9800 . ?
C2B Si1 1.8652(14) . ?
C2B H2B1 0.9800 . ?
C2B H2B2 0.9800 . ?
C2B H2B3 0.9800 . ?
C3 C4 1.3537(17) . ?
C3 C11 1.4935(17) . ?
C3 Si1 1.8790(13) . ?
C4 C10 1.5002(17) . ?
C4 C17 1.5021(17) . ?
C5 C6 1.3866(18) . ?
C5 C10 1.4040(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.3855(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.3894(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.3959(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.4150(17) . ?
C11 C16 1.3945(19) . ?
C11 C12 1.3982(19) . ?
C12 C13 1.389(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.395(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.3940(19) . ?
C17 C18 1.3959(19) . ?
C18 C19 1.3891(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.379(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.396(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?

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
C9 C1 Si1 110.49(9) . . ?
C9 C1 H1A 109.6 . . ?
Si1 C1 H1A 109.6 . . ?
C9 C1 H1B 109.6 . . ?
Si1 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
Si1 C2A H2A1 109.5 . . ?
Si1 C2A H2A2 109.5 . . ?
H2A1 C2A H2A2 109.5 . . ?
Si1 C2A H2A3 109.5 . . ?
H2A1 C2A H2A3 109.5 . . ?
H2A2 C2A H2A3 109.5 . . ?
Si1 C2B H2B1 109.5 . . ?
Si1 C2B H2B2 109.5 . . ?
H2B1 C2B H2B2 109.5 . . ?
Si1 C2B H2B3 109.5 . . ?
H2B1 C2B H2B3 109.5 . . ?
H2B2 C2B H2B3 109.5 . . ?
C4 C3 C11 123.05(11) . . ?
C4 C3 Si1 120.07(9) . . ?
C11 C3 Si1 116.74(9) . . ?
C3 C4 C10 122.91(11) . . ?
C3 C4 C17 121.46(11) . . ?
C10 C4 C17 115.37(10) . . ?
C6 C5 C10 121.70(12) . . ?
C6 C5 H5 119.2 . . ?
C10 C5 H5 119.2 . . ?
C7 C6 C5 119.91(12) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 119.37(12) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C7 C8 C9 121.60(12) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C8 C9 C10 119.20(11) . . ?
C8 C9 C1 119.86(11) . . ?
C10 C9 C1 120.92(11) . . ?
C5 C10 C9 118.12(11) . . ?
C5 C10 C4 118.42(11) . . ?
C9 C10 C4 123.33(11) . . ?
C16 C11 C12 118.38(13) . . ?
C16 C11 C3 122.03(12) . . ?
C12 C11 C3 119.49(12) . . ?
C13 C12 C11 120.92(15) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 120.28(16) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 119.58(14) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 120.62(16) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 120.22(15) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C22 C17 C18 118.89(12) . . ?
C22 C17 C4 120.27(12) . . ?
C18 C17 C4 120.83(12) . . ?
C19 C18 C17 120.72(14) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C18 120.24(15) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 119.67(14) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C20 C21 C22 120.50(15) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 119.97(15) . . ?
C17 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C2A Si1 C2B 110.41(7) . . ?
C2A Si1 C1 111.49(6) . . ?
C2B Si1 C1 111.36(7) . . ?
C2A Si1 C3 109.70(6) . . ?
C2B Si1 C3 113.05(6) . . ?
C1 Si1 C3 100.49(6) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.041


_database_code_depnum_ccdc_archive 'CCDC 989790'
