# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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
#  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_TPASi

_audit_creation_method           SHELXL-97
_chemical_name_systematic        TPASi
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 N Si'
_chemical_formula_weight         301.45

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'
N N 0.0061 0.0033 '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)/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                   11.649(4)
_cell_length_b                   8.213(3)
_cell_length_c                   17.429(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.953(4)
_cell_angle_gamma                90.00
_cell_volume                     1663.6(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9810
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            5602
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         21.57
_reflns_number_total             1917
_reflns_number_gt                1613
_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. 
;
# start Validation Reply Form
_vrf_THETM01_TPASi               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The measured crystal diffracted weakly. Although the initial measurement
was performed to a theta range up to 26 deg/2Theta, reflections at Theta values
greater than 21 deg were too weak. Therefore the data set was cut-off for angles >
21 deg/2 theta.
Nevertheless, the refined structure has a data-to-parameter ratio of 9.5
(1917 independent reflections, 1613 observed (2 sigma threshold), 201 parameters)
and therefore we believe it is well determined.
;
# end Validation Reply Form
_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)+(0.0501P)²+0.4542P] 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         1917
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0968
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.16413(18) 0.4022(3) 0.67901(12) 0.0440(6) Uani 1 1 d . . .
C2 C 0.0772(2) 0.4261(3) 0.62056(13) 0.0555(7) Uani 1 1 d . . .
H2 H 0.0718 0.3533 0.5796 0.067 Uiso 1 1 calc R . .
C3 C -0.0007(2) 0.5522(3) 0.62063(14) 0.0602(7) Uani 1 1 d . . .
H3 H -0.0573 0.5642 0.5807 0.072 Uiso 1 1 calc R . .
C4 C 0.00720(19) 0.6597(3) 0.68093(14) 0.0562(7) Uani 1 1 d . . .
H4 H -0.0442 0.7463 0.6816 0.067 Uiso 1 1 calc R . .
C5 C 0.08971(18) 0.6412(3) 0.74009(13) 0.0486(6) Uani 1 1 d . . .
H5 H 0.0931 0.7149 0.7807 0.058 Uiso 1 1 calc R . .
C6 C 0.16928(17) 0.5129(3) 0.74062(11) 0.0405(5) Uani 1 1 d . . .
C7 C 0.34192(17) 0.3844(3) 0.81420(12) 0.0423(6) Uani 1 1 d . . .
C8 C 0.41532(19) 0.3925(3) 0.88118(12) 0.0513(6) Uani 1 1 d . . .
H8 H 0.4009 0.4687 0.9188 0.062 Uiso 1 1 calc R . .
C9 C 0.5083(2) 0.2899(3) 0.89244(15) 0.0611(7) Uani 1 1 d . . .
H9 H 0.5561 0.2982 0.9372 0.073 Uiso 1 1 calc R . .
C10 C 0.5312(2) 0.1753(3) 0.83824(16) 0.0699(8) Uani 1 1 d . . .
H10 H 0.5952 0.1079 0.8452 0.084 Uiso 1 1 calc R . .
C11 C 0.4579(2) 0.1626(3) 0.77379(15) 0.0620(7) Uani 1 1 d . . .
H11 H 0.4726 0.0830 0.7378 0.074 Uiso 1 1 calc R . .
C12 C 0.36177(19) 0.2637(3) 0.75918(13) 0.0471(6) Uani 1 1 d . . .
C13 C 0.3446(2) 0.2417(3) 0.58272(14) 0.0718(8) Uani 1 1 d . . .
H13A H 0.3874 0.3414 0.5822 0.108 Uiso 1 1 calc R . .
H13B H 0.2903 0.2380 0.5387 0.108 Uiso 1 1 calc R . .
H13C H 0.3964 0.1510 0.5812 0.108 Uiso 1 1 calc R . .
C14 C 0.1932(3) 0.0299(3) 0.67479(17) 0.0790(8) Uani 1 1 d . . .
H14A H 0.2481 -0.0550 0.6675 0.118 Uiso 1 1 calc R . .
H14B H 0.1328 0.0248 0.6345 0.118 Uiso 1 1 calc R . .
H14C H 0.1611 0.0159 0.7236 0.118 Uiso 1 1 calc R . .
C15 C 0.24427(18) 0.6185(3) 0.86475(12) 0.0473(6) Uani 1 1 d . . .
C16 C 0.1768(2) 0.5883(3) 0.92504(14) 0.0624(7) Uani 1 1 d . . .
H16 H 0.1341 0.4928 0.9265 0.075 Uiso 1 1 calc R . .
C17 C 0.1735(3) 0.7031(4) 0.98394(14) 0.0760(9) Uani 1 1 d . . .
H17 H 0.1285 0.6843 1.0251 0.091 Uiso 1 1 calc R . .
C18 C 0.2364(3) 0.8432(4) 0.98093(17) 0.0802(9) Uani 1 1 d . . .
H18 H 0.2345 0.9187 1.0206 0.096 Uiso 1 1 calc R . .
C19 C 0.3016(2) 0.8735(4) 0.92096(18) 0.0763(8) Uani 1 1 d . . .
H19 H 0.3433 0.9699 0.9194 0.092 Uiso 1 1 calc R . .
C20 C 0.3059(2) 0.7612(3) 0.86234(14) 0.0599(7) Uani 1 1 d . . .
H20 H 0.3505 0.7819 0.8212 0.072 Uiso 1 1 calc R . .
N1 N 0.25071(15) 0.4991(2) 0.80416(10) 0.0461(5) Uani 1 1 d . . .
Si1 Si 0.26599(6) 0.23126(8) 0.67226(4) 0.0510(3) 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 C2 1.400(3) . ?
C1 C6 1.405(3) . ?
C1 Si1 1.847(2) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.403(3) . ?
C5 H5 0.9300 . ?
C6 N1 1.412(3) . ?
C7 C8 1.400(3) . ?
C7 C12 1.410(3) . ?
C7 N1 1.422(3) . ?
C8 C9 1.376(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.372(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.367(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.403(3) . ?
C11 H11 0.9300 . ?
C12 Si1 1.838(2) . ?
C13 Si1 1.865(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 Si1 1.860(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C20 1.377(3) . ?
C15 C16 1.377(3) . ?
C15 N1 1.447(3) . ?
C16 C17 1.396(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.367(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.357(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.380(3) . ?
C19 H19 0.9300 . ?
C20 H20 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
C2 C1 C6 117.1(2) . . ?
C2 C1 Si1 119.75(17) . . ?
C6 C1 Si1 123.14(16) . . ?
C3 C2 C1 123.3(2) . . ?
C3 C2 H2 118.4 . . ?
C1 C2 H2 118.4 . . ?
C4 C3 C2 118.4(2) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 121.2(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 119.18(19) . . ?
C5 C6 N1 118.22(18) . . ?
C1 C6 N1 122.59(19) . . ?
C8 C7 C12 118.8(2) . . ?
C8 C7 N1 118.64(19) . . ?
C12 C7 N1 122.60(19) . . ?
C9 C8 C7 121.3(2) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C10 C9 C8 120.7(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 118.5(2) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C10 C11 C12 123.3(2) . . ?
C10 C11 H11 118.3 . . ?
C12 C11 H11 118.3 . . ?
C11 C12 C7 117.3(2) . . ?
C11 C12 Si1 119.72(18) . . ?
C7 C12 Si1 122.95(17) . . ?
Si1 C13 H13A 109.5 . . ?
Si1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
Si1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Si1 C14 H14A 109.5 . . ?
Si1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Si1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 120.2(2) . . ?
C20 C15 N1 120.1(2) . . ?
C16 C15 N1 119.7(2) . . ?
C15 C16 C17 119.0(3) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C18 C17 C16 119.9(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 121.0(3) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 119.9(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C15 C20 C19 120.0(3) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C6 N1 C7 127.24(17) . . ?
C6 N1 C15 116.91(17) . . ?
C7 N1 C15 115.80(16) . . ?
C12 Si1 C1 101.16(10) . . ?
C12 Si1 C14 111.16(12) . . ?
C1 Si1 C14 112.23(12) . . ?
C12 Si1 C13 112.21(11) . . ?
C1 Si1 C13 111.90(11) . . ?
C14 Si1 C13 108.14(13) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        21.57
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.032
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane and ethanol solution'
_exptl_crystal_preparation       Luminescent
_database_code_depnum_ccdc_archive 'CCDC 1020766'
#######################################################################
#
#                 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_PhCzSi

_audit_creation_method           SHELXL-97
_chemical_name_systematic        PhCzSi
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 N Si'
_chemical_formula_weight         299.44

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'
N N 0.0061 0.0033 '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                   9.4672(19)
_cell_length_b                   17.673(4)
_cell_length_c                   10.494(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.360(2)
_cell_angle_gamma                90.00
_cell_volume                     1586.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9802
_exptl_absorpt_correction_T_max  0.9830
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            7781
_diffrn_reflns_av_R_equivalents  0.1042
_diffrn_reflns_av_sigmaI/netI    0.0694
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2795
_reflns_number_gt                2305
_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)+(0.0531P)²+0.1838P] 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         2795
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1235
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_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
C1 C 0.2446(2) 0.24146(11) 0.98863(18) 0.0397(4) Uani 1 1 d . . .
C2 C 0.2519(2) 0.31380(12) 1.04392(19) 0.0486(5) Uani 1 1 d . . .
H2 H 0.3466 0.3396 1.0773 0.058 Uiso 1 1 calc R . .
C3 C 0.1259(3) 0.34906(12) 1.0516(2) 0.0543(5) Uani 1 1 d . . .
H3 H 0.1367 0.3966 1.0928 0.065 Uiso 1 1 calc R . .
C4 C -0.0173(3) 0.31225(12) 0.9969(2) 0.0522(5) Uani 1 1 d . . .
H4 H -0.1045 0.3360 0.9981 0.063 Uiso 1 1 calc R . .
C5 C -0.0309(2) 0.24045(11) 0.94076(19) 0.0439(4) Uani 1 1 d . . .
H5 H -0.1276 0.2164 0.9033 0.053 Uiso 1 1 calc R . .
C6 C 0.0991(2) 0.20378(10) 0.93981(17) 0.0357(4) Uani 1 1 d . . .
C7 C -0.0402(2) 0.07794(10) 0.85620(17) 0.0363(4) Uani 1 1 d . . .
C8 C -0.1460(2) 0.07280(11) 0.91629(19) 0.0431(4) Uani 1 1 d . . .
H8 H -0.1472 0.1089 0.9804 0.052 Uiso 1 1 calc R . .
C9 C -0.2488(2) 0.01260(12) 0.8778(2) 0.0500(5) Uani 1 1 d . . .
H9 H -0.3199 0.0084 0.9170 0.060 Uiso 1 1 calc R . .
C10 C -0.2491(2) -0.04179(12) 0.7822(2) 0.0547(5) Uani 1 1 d . . .
H10 H -0.3218 -0.0809 0.7563 0.066 Uiso 1 1 calc R . .
C11 C -0.1418(2) -0.03795(11) 0.7257(2) 0.0493(5) Uani 1 1 d . . .
H11 H -0.1408 -0.0747 0.6627 0.059 Uiso 1 1 calc R . .
C12 C -0.0351(2) 0.02156(10) 0.76399(17) 0.0387(4) Uani 1 1 d . . .
C13 C 0.0988(2) 0.03712(10) 0.73636(17) 0.0380(4) Uani 1 1 d . . .
C14 C 0.1676(2) 0.00042(12) 0.65924(19) 0.0482(5) Uani 1 1 d . . .
H14 H 0.1218 -0.0425 0.6064 0.058 Uiso 1 1 calc R . .
C15 C 0.3051(2) 0.02916(13) 0.6630(2) 0.0540(5) Uani 1 1 d . . .
H15 H 0.3502 0.0061 0.6097 0.065 Uiso 1 1 calc R . .
C16 C 0.3770(2) 0.09179(12) 0.7449(2) 0.0478(5) Uani 1 1 d . . .
H16 H 0.4708 0.1088 0.7465 0.057 Uiso 1 1 calc R . .
C17 C 0.3143(2) 0.13039(11) 0.82502(17) 0.0389(4) Uani 1 1 d . . .
C18 C 0.1712(2) 0.10228(10) 0.81365(17) 0.0356(4) Uani 1 1 d . . .
C19 C 0.5638(3) 0.15715(15) 1.1234(2) 0.0654(6) Uani 1 1 d . . .
H19A H 0.5194 0.1135 1.1469 0.098 Uiso 1 1 calc R . .
H19B H 0.5979 0.1925 1.2003 0.098 Uiso 1 1 calc R . .
H19C H 0.6514 0.1420 1.1061 0.098 Uiso 1 1 calc R . .
C20 C 0.5097(3) 0.27795(14) 0.9030(3) 0.0709(7) Uani 1 1 d . . .
H20A H 0.5768 0.2551 0.8667 0.106 Uiso 1 1 calc R . .
H20B H 0.5704 0.3099 0.9815 0.106 Uiso 1 1 calc R . .
H20C H 0.4313 0.3077 0.8305 0.106 Uiso 1 1 calc R . .
N1 N 0.08200(16) 0.12988(8) 0.88196(14) 0.0359(3) Uani 1 1 d . . .
Si1 Si 0.41355(6) 0.20274(3) 0.96215(5) 0.0419(2) 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 C2 1.393(3) . ?
C1 C6 1.414(2) . ?
C1 Si1 1.8670(19) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(2) . ?
C5 H5 0.9300 . ?
C6 N1 1.420(2) . ?
C7 C8 1.396(3) . ?
C7 C12 1.404(2) . ?
C7 N1 1.410(2) . ?
C8 C9 1.380(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.388(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.380(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.393(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.443(3) . ?
C13 C14 1.397(3) . ?
C13 C18 1.406(2) . ?
C14 C15 1.382(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.388(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.398(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.399(2) . ?
C17 Si1 1.8521(19) . ?
C18 N1 1.408(2) . ?
C19 Si1 1.864(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 Si1 1.861(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C2 C1 C6 116.76(17) . . ?
C2 C1 Si1 120.34(15) . . ?
C6 C1 Si1 122.50(13) . . ?
C3 C2 C1 123.30(19) . . ?
C3 C2 H2 118.4 . . ?
C1 C2 H2 118.4 . . ?
C2 C3 C4 118.73(19) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 120.22(19) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.55(18) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 120.29(17) . . ?
C5 C6 N1 119.40(15) . . ?
C1 C6 N1 120.21(15) . . ?
C8 C7 C12 120.55(17) . . ?
C8 C7 N1 130.12(16) . . ?
C12 C7 N1 109.05(15) . . ?
C9 C8 C7 118.03(18) . . ?
C9 C8 H8 121.0 . . ?
C7 C8 H8 121.0 . . ?
C8 C9 C10 121.91(19) . . ?
C8 C9 H9 119.0 . . ?
C10 C9 H9 119.0 . . ?
C11 C10 C9 120.14(19) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 119.32(19) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C7 119.96(17) . . ?
C11 C12 C13 132.63(17) . . ?
C7 C12 C13 107.21(15) . . ?
C14 C13 C18 118.75(17) . . ?
C14 C13 C12 134.10(18) . . ?
C18 C13 C12 107.07(15) . . ?
C15 C14 C13 118.71(18) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 121.13(18) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C17 122.65(18) . . ?
C15 C16 H16 118.7 . . ?
C17 C16 H16 118.7 . . ?
C16 C17 C18 114.90(17) . . ?
C16 C17 Si1 126.82(15) . . ?
C18 C17 Si1 117.51(13) . . ?
C17 C18 C13 123.71(16) . . ?
C17 C18 N1 127.11(16) . . ?
C13 C18 N1 109.07(15) . . ?
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 . . ?
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 . . ?
C18 N1 C7 107.39(14) . . ?
C18 N1 C6 123.55(14) . . ?
C7 N1 C6 127.95(14) . . ?
C17 Si1 C20 113.08(10) . . ?
C17 Si1 C19 110.06(10) . . ?
C20 Si1 C19 108.63(12) . . ?
C17 Si1 C1 100.75(8) . . ?
C20 Si1 C1 111.12(10) . . ?
C19 Si1 C1 113.12(10) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.054
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane and ethanol solution'
_exptl_crystal_preparation       Luminescent
_database_code_depnum_ccdc_archive 'CCDC 1020767'
