# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2015

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1037609'
_audit_update_record             
;
2014-12-04 deposited with the CCDC.
2015-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
2,3-bis(4-chlorophenyl)-1,1-diphenyl-1H-benzo[b]silole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H22 Cl2 Si'
_chemical_formula_weight         505.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cl Cl 0.1484 0.1585 '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                   9.9590(11)
_cell_length_b                   24.396(3)
_cell_length_c                   11.0384(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.6020(10)
_cell_angle_gamma                90.00
_cell_volume                     2541.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048
_exptl_absorpt_coefficient_mu    0.322
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            41982
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         27.64
_reflns_number_total             5888
_reflns_number_gt                4863
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0429P)²+1.5588P] 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         5888
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0941
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.002
_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 0.38570(4) 0.456797(16) 0.11826(4) 0.02647(11) Uani 1 1 d . . .
Cl2 Cl 1.19812(5) 0.33634(2) 0.34587(5) 0.03556(12) Uani 1 1 d . . .
Si1 Si 0.66519(4) 0.123651(17) 0.27645(4) 0.01620(10) Uani 1 1 d . . .
C1 C 0.42714(16) 0.38824(6) 0.15788(16) 0.0194(3) Uani 1 1 d . . .
C2 C 0.50831(17) 0.37415(7) 0.28099(16) 0.0216(3) Uani 1 1 d . . .
H2 H 0.5391 0.4013 0.3456 0.026 Uiso 1 1 calc R . .
C3 C 0.54383(16) 0.31928(7) 0.30818(15) 0.0205(3) Uani 1 1 d . . .
H3 H 0.5995 0.3090 0.3922 0.025 Uiso 1 1 calc R . .
C4 C 0.49902(16) 0.27925(6) 0.21412(15) 0.0178(3) Uani 1 1 d . . .
C5 C 0.41603(17) 0.29480(7) 0.09136(16) 0.0217(3) Uani 1 1 d . . .
H5 H 0.3840 0.2677 0.0267 0.026 Uiso 1 1 calc R . .
C6 C 0.37971(17) 0.34927(7) 0.06245(16) 0.0225(3) Uani 1 1 d . . .
H6 H 0.3233 0.3597 -0.0213 0.027 Uiso 1 1 calc R . .
C7 C 0.53922(16) 0.22049(6) 0.23933(14) 0.0179(3) Uani 1 1 d . . .
C8 C 0.42549(16) 0.17968(6) 0.23277(14) 0.0178(3) Uani 1 1 d . . .
C9 C 0.28499(16) 0.19338(7) 0.21794(15) 0.0209(3) Uani 1 1 d . . .
H9 H 0.2559 0.2307 0.2095 0.025 Uiso 1 1 calc R . .
C10 C 0.18810(17) 0.15214(7) 0.21556(16) 0.0247(4) Uani 1 1 d . . .
H10 H 0.0922 0.1613 0.2043 0.030 Uiso 1 1 calc R . .
C11 C 0.22986(17) 0.09779(7) 0.22939(16) 0.0242(3) Uani 1 1 d . . .
H11 H 0.1625 0.0699 0.2271 0.029 Uiso 1 1 calc R . .
C12 C 0.37072(17) 0.08374(7) 0.24677(15) 0.0213(3) Uani 1 1 d . . .
H12 H 0.3990 0.0464 0.2575 0.026 Uiso 1 1 calc R . .
C13 C 0.47013(16) 0.12435(6) 0.24839(14) 0.0174(3) Uani 1 1 d . . .
C14 C 0.76711(16) 0.09251(6) 0.43362(14) 0.0167(3) Uani 1 1 d . . .
C15 C 0.70303(17) 0.08209(7) 0.52712(15) 0.0207(3) Uani 1 1 d . . .
H15 H 0.6060 0.0911 0.5102 0.025 Uiso 1 1 calc R . .
C16 C 0.77783(18) 0.05891(7) 0.64386(16) 0.0254(4) Uani 1 1 d . . .
H16 H 0.7314 0.0515 0.7051 0.031 Uiso 1 1 calc R . .
C17 C 0.92052(19) 0.04653(7) 0.67126(16) 0.0250(4) Uani 1 1 d . . .
H17 H 0.9723 0.0312 0.7517 0.030 Uiso 1 1 calc R . .
C18 C 0.98741(18) 0.05665(7) 0.58064(17) 0.0238(3) Uani 1 1 d . . .
H18 H 1.0851 0.0484 0.5992 0.029 Uiso 1 1 calc R . .
C19 C 0.91136(17) 0.07890(7) 0.46278(16) 0.0210(3) Uani 1 1 d . . .
H19 H 0.9575 0.0850 0.4008 0.025 Uiso 1 1 calc R . .
C20 C 0.72402(17) 0.08966(7) 0.14989(15) 0.0210(3) Uani 1 1 d . . .
C21 C 0.80636(17) 0.11598(8) 0.08597(16) 0.0248(4) Uani 1 1 d . . .
H21 H 0.8271 0.1539 0.1006 0.030 Uiso 1 1 calc R . .
C22 C 0.85875(19) 0.08745(9) 0.00081(17) 0.0324(4) Uani 1 1 d . . .
H22 H 0.9157 0.1058 -0.0410 0.039 Uiso 1 1 calc R . .
C23 C 0.8276(2) 0.03256(9) -0.02240(16) 0.0328(4) Uani 1 1 d . . .
H23 H 0.8639 0.0131 -0.0797 0.039 Uiso 1 1 calc R . .
C24 C 0.7440(3) 0.00586(8) 0.03732(19) 0.0405(5) Uani 1 1 d . . .
H24 H 0.7216 -0.0318 0.0202 0.049 Uiso 1 1 calc R . .
C25 C 0.6925(3) 0.03413(8) 0.12259(19) 0.0373(5) Uani 1 1 d . . .
H25 H 0.6349 0.0154 0.1632 0.045 Uiso 1 1 calc R . .
C26 C 0.67269(16) 0.20047(6) 0.26685(14) 0.0169(3) Uani 1 1 d . . .
C27 C 0.80075(16) 0.23434(6) 0.28166(15) 0.0169(3) Uani 1 1 d . . .
C28 C 0.80643(17) 0.27606(7) 0.19624(16) 0.0224(3) Uani 1 1 d . . .
H28 H 0.7257 0.2831 0.1240 0.027 Uiso 1 1 calc R . .
C29 C 0.92831(18) 0.30728(7) 0.21542(16) 0.0231(3) Uani 1 1 d . . .
H29 H 0.9311 0.3354 0.1566 0.028 Uiso 1 1 calc R . .
C30 C 1.04537(17) 0.29708(7) 0.32087(17) 0.0225(3) Uani 1 1 d . . .
C31 C 1.04398(18) 0.25582(7) 0.40643(17) 0.0272(4) Uani 1 1 d . . .
H31 H 1.1251 0.2490 0.4784 0.033 Uiso 1 1 calc R . .
C32 C 0.92230(17) 0.22457(7) 0.38545(16) 0.0228(3) Uani 1 1 d . . .
H32 H 0.9216 0.1958 0.4432 0.027 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
Cl1 C1 1.7446(16) . ?
Cl2 C30 1.7435(16) . ?
Si1 C13 1.8671(16) . ?
Si1 C14 1.8692(16) . ?
Si1 C20 1.8721(16) . ?
Si1 C26 1.8799(16) . ?
C1 C2 1.385(2) . ?
C1 C6 1.385(2) . ?
C2 C3 1.393(2) . ?
C3 C4 1.391(2) . ?
C4 C5 1.396(2) . ?
C4 C7 1.491(2) . ?
C5 C6 1.387(2) . ?
C7 C26 1.357(2) . ?
C7 C8 1.492(2) . ?
C8 C9 1.397(2) . ?
C8 C13 1.414(2) . ?
C9 C10 1.389(2) . ?
C10 C11 1.383(2) . ?
C11 C12 1.397(2) . ?
C12 C13 1.397(2) . ?
C14 C15 1.399(2) . ?
C14 C19 1.408(2) . ?
C15 C16 1.387(2) . ?
C16 C17 1.389(2) . ?
C17 C18 1.389(2) . ?
C18 C19 1.390(2) . ?
C20 C21 1.397(2) . ?
C20 C25 1.402(2) . ?
C21 C22 1.398(2) . ?
C22 C23 1.380(3) . ?
C23 C24 1.379(3) . ?
C24 C25 1.390(3) . ?
C26 C27 1.484(2) . ?
C27 C32 1.396(2) . ?
C27 C28 1.401(2) . ?
C28 C29 1.391(2) . ?
C29 C30 1.382(2) . ?
C30 C31 1.384(2) . ?
C31 C32 1.387(2) . ?

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
C13 Si1 C14 112.70(7) . . ?
C13 Si1 C20 115.91(7) . . ?
C14 Si1 C20 107.82(7) . . ?
C13 Si1 C26 92.26(7) . . ?
C14 Si1 C26 115.97(7) . . ?
C20 Si1 C26 111.84(7) . . ?
C2 C1 C6 121.77(15) . . ?
C2 C1 Cl1 120.09(13) . . ?
C6 C1 Cl1 118.12(13) . . ?
C1 C2 C3 118.60(15) . . ?
C4 C3 C2 120.99(15) . . ?
C3 C4 C5 118.91(15) . . ?
C3 C4 C7 122.18(14) . . ?
C5 C4 C7 118.89(14) . . ?
C6 C5 C4 120.91(15) . . ?
C1 C6 C5 118.80(15) . . ?
C26 C7 C4 125.01(14) . . ?
C26 C7 C8 116.42(14) . . ?
C4 C7 C8 118.57(13) . . ?
C9 C8 C13 120.46(14) . . ?
C9 C8 C7 124.23(14) . . ?
C13 C8 C7 115.26(13) . . ?
C10 C9 C8 119.54(15) . . ?
C11 C10 C9 120.65(15) . . ?
C10 C11 C12 120.25(15) . . ?
C11 C12 C13 120.29(15) . . ?
C12 C13 C8 118.78(14) . . ?
C12 C13 Si1 133.74(12) . . ?
C8 C13 Si1 107.39(11) . . ?
C15 C14 C19 117.43(14) . . ?
C15 C14 Si1 121.21(12) . . ?
C19 C14 Si1 121.36(12) . . ?
C16 C15 C14 121.57(15) . . ?
C15 C16 C17 120.00(16) . . ?
C16 C17 C18 119.81(16) . . ?
C17 C18 C19 120.00(15) . . ?
C18 C19 C14 121.17(15) . . ?
C21 C20 C25 117.57(16) . . ?
C21 C20 Si1 123.17(13) . . ?
C25 C20 Si1 119.13(13) . . ?
C20 C21 C22 121.06(17) . . ?
C23 C22 C21 119.88(18) . . ?
C24 C23 C22 120.24(17) . . ?
C23 C24 C25 119.90(19) . . ?
C24 C25 C20 121.31(19) . . ?
C7 C26 C27 124.78(14) . . ?
C7 C26 Si1 108.53(11) . . ?
C27 C26 Si1 126.65(11) . . ?
C32 C27 C28 117.75(14) . . ?
C32 C27 C26 119.01(14) . . ?
C28 C27 C26 123.24(14) . . ?
C29 C28 C27 121.08(15) . . ?
C30 C29 C28 119.36(15) . . ?
C29 C30 C31 121.10(15) . . ?
C29 C30 Cl2 119.57(13) . . ?
C31 C30 Cl2 119.33(13) . . ?
C30 C31 C32 118.97(15) . . ?
C31 C32 C27 121.72(15) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.64
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.050
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
