# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_ao_tr1_0m
_audit_block_doi                 10.5517/ccdc.csd.cc21cl78
_database_code_depnum_ccdc_archive 'CCDC 1887969'
loop_
_audit_author_name
_audit_author_address
'Tomasz Ratajczk'
;Institute of Physical Chemistry Polish Academy of Sciences
Poland
;
_audit_update_record             
;
2018-12-30 deposited with the CCDC.	2019-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H20 Cl2 O Si'
_chemical_formula_sum            'C27 H20 Cl2 O Si'
_chemical_formula_weight         459.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
O O 0.0492 0.0322 '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'
Cl Cl 0.3639 0.7018 '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                   12.1512(5)
_cell_length_b                   14.9012(7)
_cell_length_c                   12.3525(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.101(3)
_cell_angle_gamma                90.00
_cell_volume                     2233.36(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2531
_cell_measurement_theta_min      4.65
_cell_measurement_theta_max      67.19

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    3.259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5788
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15345
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.65
_diffrn_reflns_theta_max         66.59
_reflns_number_total             3884
_reflns_number_gt                2790
_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)+(0.0854P)²+0.8663P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3884
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1655
_refine_ls_wR_factor_gt          0.1478
_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
Cl1 Cl 0.22542(8) 0.34813(9) 0.52819(8) 0.0903(4) Uani 1 1 d . . .
Cl2 Cl 0.53808(7) 0.11252(7) 0.26572(8) 0.0766(3) Uani 1 1 d . . .
Si1 Si 0.37365(7) 0.12287(6) 0.06302(7) 0.0571(3) Uani 1 1 d . . .
O1 O 0.1902(2) 0.11180(19) -0.3996(2) 0.0824(8) Uani 1 1 d . . .
C1 C 0.4071(3) 0.2494(3) 0.4991(3) 0.0739(10) Uani 1 1 d . . .
H1 H 0.4277 0.2641 0.5705 0.089 Uiso 1 1 calc R . .
C2 C 0.3083(3) 0.2796(3) 0.4515(3) 0.0654(9) Uani 1 1 d . . .
C3 C 0.2751(3) 0.2559(2) 0.3466(3) 0.0578(8) Uani 1 1 d . . .
C4 C 0.3439(2) 0.2045(2) 0.2834(2) 0.0539(8) Uani 1 1 d . . .
C5 C 0.2938(2) 0.1892(2) 0.1657(2) 0.0508(7) Uani 1 1 d . . .
C6 C 0.3041(3) 0.1213(2) -0.0757(3) 0.0550(8) Uani 1 1 d . . .
C7 C 0.3686(3) 0.0939(3) -0.1589(3) 0.0687(10) Uani 1 1 d . . .
H7 H 0.4409 0.0762 -0.1419 0.082 Uiso 1 1 calc R . .
C8 C 0.3299(3) 0.0919(3) -0.2653(3) 0.0758(11) Uani 1 1 d . . .
H8 H 0.3757 0.0736 -0.3191 0.091 Uiso 1 1 calc R . .
C9 C 0.2221(3) 0.1175(2) -0.2922(3) 0.0606(8) Uani 1 1 d . . .
C10 C 0.0770(4) 0.1273(3) -0.4294(4) 0.0976(15) Uani 1 1 d . . .
H10A H 0.0321 0.0889 -0.3876 0.146 Uiso 1 1 calc R . .
H10B H 0.0634 0.1145 -0.5051 0.146 Uiso 1 1 calc R . .
H10C H 0.0591 0.1888 -0.4157 0.146 Uiso 1 1 calc R . .
C11 C 0.1807(2) 0.1452(2) 0.1841(3) 0.0560(8) Uani 1 1 d . . .
C12 C 0.1140(2) 0.1963(3) 0.2482(3) 0.0603(9) Uani 1 1 d . . .
C13 C 0.0087(3) 0.1670(3) 0.2699(3) 0.0737(11) Uani 1 1 d . . .
H13 H -0.0358 0.2015 0.3124 0.088 Uiso 1 1 calc R . .
C14 C -0.0289(3) 0.0866(4) 0.2278(3) 0.0857(13) Uani 1 1 d . . .
H14 H -0.0994 0.0669 0.2415 0.103 Uiso 1 1 calc R . .
C15 C 0.0372(3) 0.0352(3) 0.1657(3) 0.0846(13) Uani 1 1 d . . .
H15 H 0.0111 -0.0192 0.1379 0.101 Uiso 1 1 calc R . .
C16 C 0.1432(3) 0.0637(3) 0.1438(3) 0.0696(10) Uani 1 1 d . . .
H16 H 0.1880 0.0282 0.1026 0.083 Uiso 1 1 calc R . .
C17 C 0.1675(3) 0.2829(3) 0.2887(3) 0.0599(8) Uani 1 1 d . . .
H17 H 0.1201 0.3177 0.3348 0.072 Uiso 1 1 calc R . .
C18 C 0.1999(2) 0.3343(2) 0.1899(2) 0.0554(8) Uani 1 1 d . . .
C19 C 0.1700(3) 0.4216(3) 0.1646(3) 0.0669(9) Uani 1 1 d . . .
H19 H 0.1248 0.4537 0.2090 0.080 Uiso 1 1 calc R . .
C20 C 0.2082(3) 0.4605(3) 0.0723(3) 0.0721(10) Uani 1 1 d . . .
H20 H 0.1888 0.5192 0.0546 0.087 Uiso 1 1 calc R . .
C21 C 0.2747(3) 0.4128(3) 0.0066(3) 0.0679(9) Uani 1 1 d . . .
H21 H 0.2997 0.4394 -0.0557 0.081 Uiso 1 1 calc R . .
C22 C 0.3046(3) 0.3258(2) 0.0325(3) 0.0584(8) Uani 1 1 d . . .
H22 H 0.3502 0.2941 -0.0121 0.070 Uiso 1 1 calc R . .
C23 C 0.2671(2) 0.2851(2) 0.1248(2) 0.0512(7) Uani 1 1 d . . .
C24 C 0.1562(3) 0.1460(2) -0.2125(3) 0.0643(9) Uani 1 1 d . . .
H24 H 0.0843 0.1644 -0.2300 0.077 Uiso 1 1 calc R . .
C25 C 0.1972(3) 0.1471(3) -0.1059(3) 0.0649(9) Uani 1 1 d . . .
H25 H 0.1514 0.1660 -0.0525 0.078 Uiso 1 1 calc R . .
C26 C 0.4433(3) 0.1759(2) 0.3322(3) 0.0587(8) Uani 1 1 d . . .
C27 C 0.4738(3) 0.1975(3) 0.4392(3) 0.0673(9) Uani 1 1 d . . .
H27 H 0.5402 0.1765 0.4704 0.081 Uiso 1 1 calc R . .
H1SI H 0.477(2) 0.1627(19) 0.051(2) 0.047(8) Uiso 1 1 d . . .
H2SI H 0.385(3) 0.031(2) 0.094(3) 0.059(9) Uiso 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
Cl1 C2 1.748(4) . ?
Cl2 C26 1.731(4) . ?
Si1 C6 1.869(3) . ?
Si1 C5 1.913(3) . ?
Si1 H1SI 1.41(3) . ?
Si1 H2SI 1.42(3) . ?
O1 C9 1.365(4) . ?
O1 C10 1.423(5) . ?
C1 C27 1.365(5) . ?
C1 C2 1.383(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.382(5) . ?
C3 C4 1.402(5) . ?
C3 C17 1.510(4) . ?
C4 C26 1.388(4) . ?
C4 C5 1.563(4) . ?
C5 C23 1.545(4) . ?
C5 C11 1.551(4) . ?
C6 C25 1.387(4) . ?
C6 C7 1.387(5) . ?
C7 C8 1.373(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(5) . ?
C8 H8 0.9300 . ?
C9 C24 1.369(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C16 1.380(5) . ?
C11 C12 1.390(5) . ?
C12 C13 1.392(5) . ?
C12 C17 1.517(5) . ?
C13 C14 1.374(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.396(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.511(5) . ?
C17 H17 0.9800 . ?
C18 C19 1.381(5) . ?
C18 C23 1.387(4) . ?
C19 C20 1.381(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.374(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.380(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.390(4) . ?
C22 H22 0.9300 . ?
C24 C25 1.382(5) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C27 1.392(5) . ?
C27 H27 0.9300 . ?

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
C6 Si1 C5 113.19(13) . . ?
C6 Si1 H1SI 105.8(12) . . ?
C5 Si1 H1SI 109.9(12) . . ?
C6 Si1 H2SI 105.2(13) . . ?
C5 Si1 H2SI 111.4(12) . . ?
H1SI Si1 H2SI 111.1(17) . . ?
C9 O1 C10 117.5(3) . . ?
C27 C1 C2 118.8(3) . . ?
C27 C1 H1 120.6 . . ?
C2 C1 H1 120.6 . . ?
C3 C2 C1 121.2(4) . . ?
C3 C2 Cl1 120.6(3) . . ?
C1 C2 Cl1 118.2(3) . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 C17 125.2(3) . . ?
C4 C3 C17 114.1(3) . . ?
C26 C4 C3 117.2(3) . . ?
C26 C4 C5 130.2(3) . . ?
C3 C4 C5 112.6(2) . . ?
C23 C5 C11 105.5(2) . . ?
C23 C5 C4 103.5(2) . . ?
C11 C5 C4 103.2(2) . . ?
C23 C5 Si1 111.5(2) . . ?
C11 C5 Si1 111.4(2) . . ?
C4 C5 Si1 120.4(2) . . ?
C25 C6 C7 116.1(3) . . ?
C25 C6 Si1 127.9(3) . . ?
C7 C6 Si1 115.9(2) . . ?
C8 C7 C6 122.5(3) . . ?
C8 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C7 C8 C9 119.6(3) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
O1 C9 C24 124.8(3) . . ?
O1 C9 C8 115.5(3) . . ?
C24 C9 C8 119.7(3) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 119.8(3) . . ?
C16 C11 C5 126.6(3) . . ?
C12 C11 C5 113.6(3) . . ?
C11 C12 C13 120.5(4) . . ?
C11 C12 C17 113.7(3) . . ?
C13 C12 C17 125.9(3) . . ?
C14 C13 C12 119.5(4) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 120.3(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 120.8(4) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C11 C16 C15 119.2(4) . . ?
C11 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C3 C17 C18 105.1(3) . . ?
C3 C17 C12 105.9(3) . . ?
C18 C17 C12 106.9(3) . . ?
C3 C17 H17 112.8 . . ?
C18 C17 H17 112.8 . . ?
C12 C17 H17 112.8 . . ?
C19 C18 C23 121.4(3) . . ?
C19 C18 C17 125.7(3) . . ?
C23 C18 C17 112.8(3) . . ?
C20 C19 C18 119.1(3) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C21 C20 C19 120.4(4) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 120.3(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C23 120.4(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C18 C23 C22 118.4(3) . . ?
C18 C23 C5 114.8(3) . . ?
C22 C23 C5 126.8(3) . . ?
C9 C24 C25 119.5(3) . . ?
C9 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C24 C25 C6 122.5(3) . . ?
C24 C25 H25 118.7 . . ?
C6 C25 H25 118.7 . . ?
C4 C26 C27 121.5(3) . . ?
C4 C26 Cl2 123.2(3) . . ?
C27 C26 Cl2 115.3(2) . . ?
C1 C27 C26 120.7(3) . . ?
C1 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        66.59
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_ao_y_0m
_audit_block_doi                 10.5517/ccdc.csd.cc21clhj
_database_code_depnum_ccdc_archive 'CCDC 1887977'
loop_
_audit_author_name
_audit_author_address
'Tomasz Ratajczk'
;Institute of Physical Chemistry Polish Academy of Sciences
Poland
;
_audit_update_record             
;
2018-12-30 deposited with the CCDC.	2019-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H22 O Si'
_chemical_formula_weight         390.54

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'
O O 0.0492 0.0322 '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                   11.7985(5)
_cell_length_b                   11.7703(5)
_cell_length_c                   15.4232(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.149(3)
_cell_angle_gamma                90.00
_cell_volume                     2125.20(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1595
_cell_measurement_theta_min      4.74
_cell_measurement_theta_max      66.35

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    1.076
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9038
_exptl_absorpt_correction_T_max  0.9502
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11605
_diffrn_reflns_av_R_equivalents  0.1114
_diffrn_reflns_av_sigmaI/netI    0.0755
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.74
_diffrn_reflns_theta_max         65.08
_reflns_number_total             3559
_reflns_number_gt                2180
_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)+(0.0816P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3559
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.1553
_refine_ls_wR_factor_gt          0.1356
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_restrained_S_all      0.921
_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 0.89544(8) 0.91689(8) 0.12535(6) 0.0611(3) Uani 1 1 d . . .
C1 C 0.5323(4) 1.2098(4) 0.3621(3) 0.1005(15) Uani 1 1 d . . .
H1A H 0.4788 1.2039 0.3101 0.151 Uiso 1 1 calc R . .
H1B H 0.5091 1.2697 0.3983 0.151 Uiso 1 1 calc R . .
H1C H 0.5346 1.1393 0.3935 0.151 Uiso 1 1 calc R . .
O1 O 0.6413(2) 1.2340(2) 0.33930(18) 0.0849(8) Uani 1 1 d . . .
C3 C 0.6926(3) 1.1530(3) 0.29320(19) 0.0551(7) Uani 1 1 d . . .
C4 C 0.6462(2) 1.0493(3) 0.26875(18) 0.0531(7) Uani 1 1 d . . .
H4 H 0.5760 1.0280 0.2850 0.064 Uiso 1 1 calc R . .
C5 C 0.7052(3) 0.9764(3) 0.21939(19) 0.0544(7) Uani 1 1 d . . .
H5 H 0.6734 0.9060 0.2033 0.065 Uiso 1 1 calc R . .
C6 C 0.8094(2) 1.0050(2) 0.19353(19) 0.0508(7) Uani 1 1 d . . .
C7 C 0.8267(2) 0.7832(2) 0.07647(17) 0.0458(7) Uani 1 1 d . . .
C8 C 0.9029(2) 0.7202(3) 0.01728(17) 0.0485(7) Uani 1 1 d . . .
C9 C 1.0093(3) 0.7521(3) -0.0024(2) 0.0627(9) Uani 1 1 d . . .
H9 H 1.0452 0.8160 0.0236 0.075 Uiso 1 1 calc R . .
C10 C 1.0627(3) 0.6877(4) -0.0618(2) 0.0727(11) Uani 1 1 d . . .
H10 H 1.1344 0.7092 -0.0750 0.087 Uiso 1 1 calc R . .
C11 C 1.0113(3) 0.5940(3) -0.1007(2) 0.0686(10) Uani 1 1 d . . .
H11 H 1.0470 0.5534 -0.1413 0.082 Uiso 1 1 calc R . .
C12 C 0.5106(4) 0.8007(5) -0.0971(2) 0.0920(15) Uani 1 1 d . . .
H12 H 0.4422 0.8016 -0.1343 0.110 Uiso 1 1 calc R . .
C13 C 0.5639(3) 0.6984(4) -0.0754(2) 0.0780(11) Uani 1 1 d . . .
H13 H 0.5321 0.6306 -0.0975 0.094 Uiso 1 1 calc R . .
C14 C 0.6658(2) 0.6987(3) -0.01995(17) 0.0553(8) Uani 1 1 d . . .
C15 C 0.7367(2) 0.5954(3) 0.00658(19) 0.0546(7) Uani 1 1 d . . .
H15 H 0.7034 0.5252 -0.0195 0.066 Uiso 1 1 calc R . .
C16 C 0.8527(2) 0.6219(3) -0.02082(17) 0.0491(7) Uani 1 1 d . . .
C17 C 0.9060(3) 0.5590(3) -0.07985(18) 0.0620(9) Uani 1 1 d . . .
H17 H 0.8714 0.4940 -0.1052 0.074 Uiso 1 1 calc R . .
C18 C 0.7994(2) 0.6929(2) 0.14327(16) 0.0428(6) Uani 1 1 d . . .
C19 C 0.7507(2) 0.5934(2) 0.10584(18) 0.0468(7) Uani 1 1 d . . .
C20 C 0.7196(3) 0.5063(3) 0.1579(2) 0.0600(8) Uani 1 1 d . . .
H20 H 0.6863 0.4405 0.1329 0.072 Uiso 1 1 calc R . .
C21 C 0.7387(3) 0.5183(3) 0.2483(2) 0.0696(10) Uani 1 1 d . . .
H21 H 0.7176 0.4601 0.2838 0.084 Uiso 1 1 calc R . .
C22 C 0.7879(3) 0.6141(3) 0.2854(2) 0.0645(9) Uani 1 1 d . . .
H22 H 0.8005 0.6204 0.3459 0.077 Uiso 1 1 calc R . .
C23 C 0.8192(2) 0.7024(3) 0.23386(17) 0.0515(7) Uani 1 1 d . . .
H23 H 0.8531 0.7674 0.2596 0.062 Uiso 1 1 calc R . .
C24 C 0.7979(3) 1.1835(3) 0.2692(2) 0.0638(8) Uani 1 1 d . . .
H24 H 0.8300 1.2535 0.2862 0.077 Uiso 1 1 calc R . .
C25 C 0.8542(3) 1.1105(3) 0.2206(2) 0.0571(8) Uani 1 1 d . . .
H25 H 0.9248 1.1320 0.2051 0.069 Uiso 1 1 calc R . .
C26 C 0.7124(2) 0.7995(3) 0.01544(17) 0.0512(7) Uani 1 1 d . . .
C27 C 0.6593(3) 0.9017(3) -0.00644(19) 0.0643(9) Uani 1 1 d . . .
H27 H 0.6900 0.9696 0.0166 0.077 Uiso 1 1 calc R . .
C28 C 0.5570(3) 0.9005(4) -0.0648(2) 0.0848(13) Uani 1 1 d . . .
H28 H 0.5208 0.9687 -0.0814 0.102 Uiso 1 1 calc R . .
H1SI H 0.995(2) 0.891(2) 0.1719(17) 0.050(7) Uiso 1 1 d . . .
H2SI H 0.919(2) 0.986(3) 0.0563(18) 0.060(8) Uiso 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
Si1 C6 1.865(3) . ?
Si1 C7 1.884(3) . ?
Si1 H1SI 1.33(3) . ?
Si1 H2SI 1.40(3) . ?
C1 O1 1.404(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
O1 C3 1.374(4) . ?
C3 C4 1.371(4) . ?
C3 C24 1.387(4) . ?
C4 C5 1.390(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(4) . ?
C5 H5 0.9300 . ?
C6 C25 1.394(4) . ?
C7 C18 1.542(4) . ?
C7 C8 1.548(4) . ?
C7 C26 1.557(4) . ?
C8 C9 1.380(4) . ?
C8 C16 1.396(4) . ?
C9 C10 1.398(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.361(5) . ?
C10 H10 0.9300 . ?
C11 C17 1.384(5) . ?
C11 H11 0.9300 . ?
C12 C28 1.364(6) . ?
C12 C13 1.380(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.385(4) . ?
C13 H13 0.9300 . ?
C14 C26 1.390(4) . ?
C14 C15 1.503(4) . ?
C15 C16 1.514(4) . ?
C15 C19 1.519(4) . ?
C15 H15 0.9800 . ?
C16 C17 1.383(4) . ?
C17 H17 0.9300 . ?
C18 C23 1.392(4) . ?
C18 C19 1.397(4) . ?
C19 C20 1.381(4) . ?
C20 C21 1.391(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.361(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.386(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.366(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C27 1.379(4) . ?
C27 C28 1.413(5) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?

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
C6 Si1 C7 116.89(12) . . ?
C6 Si1 H1SI 109.0(11) . . ?
C7 Si1 H1SI 109.5(12) . . ?
C6 Si1 H2SI 106.1(12) . . ?
C7 Si1 H2SI 107.4(12) . . ?
H1SI Si1 H2SI 107.5(17) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 O1 C1 117.7(3) . . ?
C4 C3 O1 125.0(3) . . ?
C4 C3 C24 119.8(3) . . ?
O1 C3 C24 115.1(3) . . ?
C3 C4 C5 119.4(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 122.2(3) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C25 116.7(3) . . ?
C5 C6 Si1 126.5(2) . . ?
C25 C6 Si1 116.8(2) . . ?
C18 C7 C8 104.4(2) . . ?
C18 C7 C26 104.6(2) . . ?
C8 C7 C26 103.0(2) . . ?
C18 C7 Si1 115.08(19) . . ?
C8 C7 Si1 112.6(2) . . ?
C26 C7 Si1 115.9(2) . . ?
C9 C8 C16 118.8(3) . . ?
C9 C8 C7 127.6(3) . . ?
C16 C8 C7 113.5(2) . . ?
C8 C9 C10 119.5(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 121.0(3) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C17 120.2(3) . . ?
C10 C11 H11 119.9 . . ?
C17 C11 H11 119.9 . . ?
C28 C12 C13 120.8(3) . . ?
C28 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C14 118.9(4) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C13 C14 C26 120.9(3) . . ?
C13 C14 C15 125.3(3) . . ?
C26 C14 C15 113.8(2) . . ?
C14 C15 C16 104.5(3) . . ?
C14 C15 C19 105.9(2) . . ?
C16 C15 C19 107.2(2) . . ?
C14 C15 H15 112.9 . . ?
C16 C15 H15 112.9 . . ?
C19 C15 H15 112.9 . . ?
C17 C16 C8 121.2(3) . . ?
C17 C16 C15 125.0(3) . . ?
C8 C16 C15 113.8(2) . . ?
C16 C17 C11 119.2(3) . . ?
C16 C17 H17 120.4 . . ?
C11 C17 H17 120.4 . . ?
C23 C18 C19 119.4(2) . . ?
C23 C18 C7 126.3(3) . . ?
C19 C18 C7 114.3(2) . . ?
C20 C19 C18 120.5(3) . . ?
C20 C19 C15 126.4(3) . . ?
C18 C19 C15 113.0(2) . . ?
C19 C20 C21 119.0(3) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C22 C21 C20 120.9(3) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 C23 120.6(3) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C18 119.5(3) . . ?
C22 C23 H23 120.3 . . ?
C18 C23 H23 120.3 . . ?
C25 C24 C3 119.8(3) . . ?
C25 C24 H24 120.1 . . ?
C3 C24 H24 120.1 . . ?
C24 C25 C6 122.2(3) . . ?
C24 C25 H25 118.9 . . ?
C6 C25 H25 118.9 . . ?
C27 C26 C14 120.2(3) . . ?
C27 C26 C7 126.0(3) . . ?
C14 C26 C7 113.8(2) . . ?
C26 C27 C28 118.3(4) . . ?
C26 C27 H27 120.9 . . ?
C28 C27 H27 120.9 . . ?
C12 C28 C27 120.9(3) . . ?
C12 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?

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 O1 C3 C4 -1.0(5) . . . . ?
C1 O1 C3 C24 177.3(4) . . . . ?
O1 C3 C4 C5 177.7(3) . . . . ?
C24 C3 C4 C5 -0.6(5) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C4 C5 C6 C25 1.1(5) . . . . ?
C4 C5 C6 Si1 -178.5(2) . . . . ?
C7 Si1 C6 C5 7.3(3) . . . . ?
C7 Si1 C6 C25 -172.2(2) . . . . ?
C6 Si1 C7 C18 -63.7(2) . . . . ?
C6 Si1 C7 C8 176.95(18) . . . . ?
C6 Si1 C7 C26 58.7(2) . . . . ?
C18 C7 C8 C9 -126.3(3) . . . . ?
C26 C7 C8 C9 124.7(3) . . . . ?
Si1 C7 C8 C9 -0.9(4) . . . . ?
C18 C7 C8 C16 55.6(3) . . . . ?
C26 C7 C8 C16 -53.4(3) . . . . ?
Si1 C7 C8 C16 -178.98(18) . . . . ?
C16 C8 C9 C10 2.0(4) . . . . ?
C7 C8 C9 C10 -176.0(3) . . . . ?
C8 C9 C10 C11 0.1(5) . . . . ?
C9 C10 C11 C17 -1.9(5) . . . . ?
C28 C12 C13 C14 0.0(6) . . . . ?
C12 C13 C14 C26 1.8(5) . . . . ?
C12 C13 C14 C15 -177.1(3) . . . . ?
C13 C14 C15 C16 122.8(3) . . . . ?
C26 C14 C15 C16 -56.1(3) . . . . ?
C13 C14 C15 C19 -124.1(3) . . . . ?
C26 C14 C15 C19 56.9(3) . . . . ?
C9 C8 C16 C17 -2.3(4) . . . . ?
C7 C8 C16 C17 176.0(2) . . . . ?
C9 C8 C16 C15 179.5(3) . . . . ?
C7 C8 C16 C15 -2.3(3) . . . . ?
C14 C15 C16 C17 -119.7(3) . . . . ?
C19 C15 C16 C17 128.2(3) . . . . ?
C14 C15 C16 C8 58.4(3) . . . . ?
C19 C15 C16 C8 -53.7(3) . . . . ?
C8 C16 C17 C11 0.6(4) . . . . ?
C15 C16 C17 C11 178.6(3) . . . . ?
C10 C11 C17 C16 1.5(5) . . . . ?
C8 C7 C18 C23 124.9(3) . . . . ?
C26 C7 C18 C23 -127.3(3) . . . . ?
Si1 C7 C18 C23 1.0(3) . . . . ?
C8 C7 C18 C19 -54.9(3) . . . . ?
C26 C7 C18 C19 53.0(3) . . . . ?
Si1 C7 C18 C19 -178.71(18) . . . . ?
C23 C18 C19 C20 1.7(4) . . . . ?
C7 C18 C19 C20 -178.6(2) . . . . ?
C23 C18 C19 C15 -178.9(2) . . . . ?
C7 C18 C19 C15 0.8(3) . . . . ?
C14 C15 C19 C20 122.6(3) . . . . ?
C16 C15 C19 C20 -126.3(3) . . . . ?
C14 C15 C19 C18 -56.7(3) . . . . ?
C16 C15 C19 C18 54.4(3) . . . . ?
C18 C19 C20 C21 -0.8(4) . . . . ?
C15 C19 C20 C21 179.9(3) . . . . ?
C19 C20 C21 C22 -0.3(5) . . . . ?
C20 C21 C22 C23 0.5(5) . . . . ?
C21 C22 C23 C18 0.4(5) . . . . ?
C19 C18 C23 C22 -1.5(4) . . . . ?
C7 C18 C23 C22 178.8(3) . . . . ?
C4 C3 C24 C25 0.6(5) . . . . ?
O1 C3 C24 C25 -177.8(3) . . . . ?
C3 C24 C25 C6 0.2(5) . . . . ?
C5 C6 C25 C24 -1.0(5) . . . . ?
Si1 C6 C25 C24 178.6(3) . . . . ?
C13 C14 C26 C27 -2.0(4) . . . . ?
C15 C14 C26 C27 177.0(2) . . . . ?
C13 C14 C26 C7 179.7(3) . . . . ?
C15 C14 C26 C7 -1.2(3) . . . . ?
C18 C7 C26 C27 128.9(3) . . . . ?
C8 C7 C26 C27 -122.3(3) . . . . ?
Si1 C7 C26 C27 1.1(3) . . . . ?
C18 C7 C26 C14 -53.0(3) . . . . ?
C8 C7 C26 C14 55.8(3) . . . . ?
Si1 C7 C26 C14 179.17(19) . . . . ?
C14 C26 C27 C28 0.4(4) . . . . ?
C7 C26 C27 C28 178.4(3) . . . . ?
C13 C12 C28 C27 -1.6(6) . . . . ?
C26 C27 C28 C12 1.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        65.08
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.045
