# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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
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# 
#  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.
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data_dan7545

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H24 Si'
_chemical_formula_weight         304.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.2541 0.3302 '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                   7.5625(6)
_cell_length_b                   8.5844(6)
_cell_length_c                   14.9024(15)
_cell_angle_alpha                105.447(4)
_cell_angle_beta                 98.731(5)
_cell_angle_gamma                99.813(4)
_cell_volume                     898.84(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    2573
_cell_measurement_theta_min      0.88
_cell_measurement_theta_max      68.25

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    1.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8123
_exptl_absorpt_correction_T_max  0.9579
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10040
_diffrn_reflns_av_R_equivalents  0.057
_diffrn_reflns_av_sigmaI/netI    0.0604
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         66.53
_reflns_number_total             3007
_reflns_number_gt                2606
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0896P)²+0.1168P] 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         3007
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1581
_refine_ls_wR_factor_gt          0.1526
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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 0.31624(7) 0.48881(7) 0.25245(3) 0.0533(2) Uani 1 1 d . . .
C1 C 0.5720(3) 0.5523(3) 0.26005(13) 0.0571(5) Uani 1 1 d . . .
H1 H 0.6415 0.5427 0.3195 0.068 Uiso 1 1 calc R . .
C2 C 0.6300(3) 0.4490(3) 0.17332(14) 0.0577(5) Uani 1 1 d . . .
C3 C 0.6524(3) 0.5567(3) 0.11209(15) 0.0668(6) Uani 1 1 d . . .
H3 H 0.6672 0.5201 0.0489 0.080 Uiso 1 1 calc R . .
C4 C 0.6491(3) 0.7120(3) 0.15678(18) 0.0724(6) Uani 1 1 d . . .
H4 H 0.6632 0.7986 0.1291 0.087 Uiso 1 1 calc R . .
C5 C 0.6207(3) 0.7337(3) 0.25565(16) 0.0694(6) Uani 1 1 d . . .
H5A H 0.5201 0.7898 0.2671 0.083 Uiso 1 1 calc R . .
H5B H 0.7324 0.7975 0.3025 0.083 Uiso 1 1 calc R . .
C6 C 0.6631(3) 0.2956(3) 0.15690(15) 0.0612(5) Uani 1 1 d . . .
C7 C 0.7123(4) 0.2063(4) 0.06529(18) 0.0809(7) Uani 1 1 d . . .
H7A H 0.7021 0.2709 0.0211 0.121 Uiso 1 1 calc R . .
H7B H 0.6291 0.0986 0.0376 0.121 Uiso 1 1 calc R . .
H7C H 0.8371 0.1921 0.0784 0.121 Uiso 1 1 calc R . .
C8 C 0.6617(4) 0.2021(4) 0.22838(19) 0.0776(7) Uani 1 1 d . . .
H8A H 0.6447 0.2724 0.2878 0.116 Uiso 1 1 calc R . .
H8B H 0.7775 0.1688 0.2391 0.116 Uiso 1 1 calc R . .
H8C H 0.5621 0.1045 0.2047 0.116 Uiso 1 1 calc R . .
C9 C 0.1888(3) 0.5189(3) 0.14317(14) 0.0637(6) Uani 1 1 d . . .
H9A H 0.0592 0.5036 0.1444 0.096 Uiso 1 1 calc R . .
H9B H 0.2059 0.4387 0.0873 0.096 Uiso 1 1 calc R . .
H9C H 0.2351 0.6300 0.1409 0.096 Uiso 1 1 calc R . .
C11 C 0.2390(3) 0.2666(3) 0.24874(14) 0.0561(5) Uani 1 1 d . . .
C12 C 0.1815(3) 0.1372(3) 0.16312(16) 0.0667(6) Uani 1 1 d . . .
H12 H 0.1837 0.1613 0.1053 0.080 Uiso 1 1 calc R . .
C13 C 0.1215(4) -0.0249(3) 0.16164(19) 0.0771(7) Uani 1 1 d . . .
H13 H 0.0820 -0.1091 0.1031 0.093 Uiso 1 1 calc R . .
C14 C 0.1192(4) -0.0641(3) 0.2455(2) 0.0777(7) Uani 1 1 d . . .
H14 H 0.0777 -0.1744 0.2443 0.093 Uiso 1 1 calc R . .
C15 C 0.1780(3) 0.0595(4) 0.33062(19) 0.0729(7) Uani 1 1 d . . .
H15 H 0.1793 0.0334 0.3881 0.087 Uiso 1 1 calc R . .
C16 C 0.2356(3) 0.2225(3) 0.33229(16) 0.0649(6) Uani 1 1 d . . .
H16 H 0.2734 0.3057 0.3912 0.078 Uiso 1 1 calc R . .
C21 C 0.2571(3) 0.6199(3) 0.36191(13) 0.0566(5) Uani 1 1 d . . .
C22 C 0.0752(3) 0.6067(3) 0.37043(15) 0.0671(6) Uani 1 1 d . . .
H22 H -0.0172 0.5341 0.3201 0.080 Uiso 1 1 calc R . .
C23 C 0.0259(3) 0.6975(4) 0.45091(16) 0.0765(7) Uani 1 1 d . . .
H23 H -0.0985 0.6855 0.4546 0.092 Uiso 1 1 calc R . .
C24 C 0.1593(3) 0.8056(4) 0.52577(15) 0.0733(7) Uani 1 1 d . . .
H24 H 0.1265 0.8676 0.5804 0.088 Uiso 1 1 calc R . .
C25 C 0.3399(3) 0.8215(4) 0.51939(15) 0.0741(7) Uani 1 1 d . . .
H25 H 0.4312 0.8952 0.5699 0.089 Uiso 1 1 calc R . .
C26 C 0.3896(3) 0.7297(3) 0.43915(15) 0.0665(6) Uani 1 1 d . . .
H26 H 0.5145 0.7414 0.4365 0.080 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 C9 1.866(2) . ?
Si1 C11 1.880(2) . ?
Si1 C21 1.882(2) . ?
Si1 C1 1.895(2) . ?
C1 C2 1.531(3) . ?
C1 C5 1.559(3) . ?
C1 H1 0.9900 . ?
C2 C6 1.348(3) . ?
C2 C3 1.469(3) . ?
C3 C4 1.329(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.489(3) . ?
C4 H4 0.9400 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C6 C8 1.495(4) . ?
C6 C7 1.511(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C11 C16 1.397(3) . ?
C11 C12 1.401(3) . ?
C12 C13 1.382(4) . ?
C12 H12 0.9400 . ?
C13 C14 1.380(4) . ?
C13 H13 0.9400 . ?
C14 C15 1.372(4) . ?
C14 H14 0.9400 . ?
C15 C16 1.386(4) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?
C21 C22 1.388(3) . ?
C21 C26 1.403(3) . ?
C22 C23 1.386(3) . ?
C22 H22 0.9400 . ?
C23 C24 1.383(4) . ?
C23 H23 0.9400 . ?
C24 C25 1.370(3) . ?
C24 H24 0.9400 . ?
C25 C26 1.388(3) . ?
C25 H25 0.9400 . ?
C26 H26 0.9400 . ?

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 Si1 C11 108.33(10) . . ?
C9 Si1 C21 110.44(10) . . ?
C11 Si1 C21 106.79(9) . . ?
C9 Si1 C1 109.49(9) . . ?
C11 Si1 C1 113.15(10) . . ?
C21 Si1 C1 108.61(9) . . ?
C2 C1 C5 104.50(17) . . ?
C2 C1 Si1 111.36(14) . . ?
C5 C1 Si1 109.42(15) . . ?
C2 C1 H1 110.5 . . ?
C5 C1 H1 110.5 . . ?
Si1 C1 H1 110.5 . . ?
C6 C2 C3 126.3(2) . . ?
C6 C2 C1 128.52(19) . . ?
C3 C2 C1 105.13(19) . . ?
C4 C3 C2 111.8(2) . . ?
C4 C3 H3 124.1 . . ?
C2 C3 H3 124.1 . . ?
C3 C4 C5 112.4(2) . . ?
C3 C4 H4 123.8 . . ?
C5 C4 H4 123.8 . . ?
C4 C5 C1 103.29(19) . . ?
C4 C5 H5A 111.1 . . ?
C1 C5 H5A 111.1 . . ?
C4 C5 H5B 111.1 . . ?
C1 C5 H5B 111.1 . . ?
H5A C5 H5B 109.1 . . ?
C2 C6 C8 123.3(2) . . ?
C2 C6 C7 122.4(2) . . ?
C8 C6 C7 114.3(2) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
Si1 C9 H9A 109.5 . . ?
Si1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
Si1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C16 C11 C12 116.5(2) . . ?
C16 C11 Si1 121.17(17) . . ?
C12 C11 Si1 122.35(16) . . ?
C13 C12 C11 121.6(2) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 119.4(2) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 120.3(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 121.8(2) . . ?
C15 C16 H16 119.1 . . ?
C11 C16 H16 119.1 . . ?
C22 C21 C26 116.7(2) . . ?
C22 C21 Si1 120.10(16) . . ?
C26 C21 Si1 123.17(16) . . ?
C23 C22 C21 122.0(2) . . ?
C23 C22 H22 119.0 . . ?
C21 C22 H22 119.0 . . ?
C24 C23 C22 120.1(2) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C24 C23 119.2(2) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 120.7(2) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C25 C26 C21 121.2(2) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?

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
C9 Si1 C1 C2 -59.86(17) . . . . ?
C11 Si1 C1 C2 61.08(16) . . . . ?
C21 Si1 C1 C2 179.47(14) . . . . ?
C9 Si1 C1 C5 55.16(16) . . . . ?
C11 Si1 C1 C5 176.10(13) . . . . ?
C21 Si1 C1 C5 -65.51(15) . . . . ?
C5 C1 C2 C6 160.8(2) . . . . ?
Si1 C1 C2 C6 -81.1(2) . . . . ?
C5 C1 C2 C3 -16.2(2) . . . . ?
Si1 C1 C2 C3 101.82(17) . . . . ?
C6 C2 C3 C4 -165.9(2) . . . . ?
C1 C2 C3 C4 11.3(2) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 C1 -9.5(3) . . . . ?
C2 C1 C5 C4 15.4(2) . . . . ?
Si1 C1 C5 C4 -103.89(17) . . . . ?
C3 C2 C6 C8 171.5(2) . . . . ?
C1 C2 C6 C8 -5.0(4) . . . . ?
C3 C2 C6 C7 -6.1(3) . . . . ?
C1 C2 C6 C7 177.4(2) . . . . ?
C9 Si1 C11 C16 -148.85(18) . . . . ?
C21 Si1 C11 C16 -29.9(2) . . . . ?
C1 Si1 C11 C16 89.55(19) . . . . ?
C9 Si1 C11 C12 30.9(2) . . . . ?
C21 Si1 C11 C12 149.84(18) . . . . ?
C1 Si1 C11 C12 -90.72(19) . . . . ?
C16 C11 C12 C13 1.1(3) . . . . ?
Si1 C11 C12 C13 -178.61(19) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C13 C14 C15 C16 1.3(4) . . . . ?
C14 C15 C16 C11 -1.1(4) . . . . ?
C12 C11 C16 C15 -0.1(3) . . . . ?
Si1 C11 C16 C15 179.61(17) . . . . ?
C9 Si1 C21 C22 55.0(2) . . . . ?
C11 Si1 C21 C22 -62.6(2) . . . . ?
C1 Si1 C21 C22 175.04(18) . . . . ?
C9 Si1 C21 C26 -127.2(2) . . . . ?
C11 Si1 C21 C26 115.2(2) . . . . ?
C1 Si1 C21 C26 -7.1(2) . . . . ?
C26 C21 C22 C23 0.2(4) . . . . ?
Si1 C21 C22 C23 178.2(2) . . . . ?
C21 C22 C23 C24 0.2(4) . . . . ?
C22 C23 C24 C25 -0.1(4) . . . . ?
C23 C24 C25 C26 -0.4(4) . . . . ?
C24 C25 C26 C21 0.8(4) . . . . ?
C22 C21 C26 C25 -0.7(4) . . . . ?
Si1 C21 C26 C25 -178.60(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.952
_diffrn_reflns_theta_full        66.53
_diffrn_measured_fraction_theta_full 0.952
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.044
#=============================================================================
#  end of cif data for "dan7545" (compound 5) 
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================
_database_code_depnum_ccdc_archive 'CCDC 1008790'
