# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_4
_database_code_depnum_ccdc_archive 'CCDC 1418862'
_audit_update_record             
;
2015-10-26 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H34 Cl4 N2 Si2'
_chemical_formula_sum            'C24 H34 Cl4 N2 Si2'
_chemical_formula_weight         548.51

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'
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)/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                   9.730(6)
_cell_length_b                   11.344(7)
_cell_length_c                   13.051(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.115(9)
_cell_angle_gamma                90.00
_cell_volume                     1432.3(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    5072
_cell_measurement_theta_min      1.6
_cell_measurement_theta_max      28.0

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.512
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8956
_exptl_absorpt_correction_T_max  0.9134
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(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  'Rigaku Saturn CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12871
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_sigmaI/netI    0.0645
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         27.91
_reflns_number_total             3411
_reflns_number_gt                2294
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r2'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0362P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3411
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0818
_refine_ls_wR_factor_gt          0.0791
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_restrained_S_all      0.923
_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
Si1 Si 0.07677(5) 0.08366(4) -0.01468(3) 0.01633(12) Uani 1 1 d . . .
N1 N 0.00087(15) 0.02844(11) 0.08810(9) 0.0155(3) Uani 1 1 d . . .
Cl1 Cl 0.28637(5) 0.08484(4) -0.00020(3) 0.02446(12) Uani 1 1 d . . .
Cl2 Cl 0.02062(5) 0.24994(4) -0.05873(3) 0.02653(13) Uani 1 1 d . . .
C1 C 0.00128(18) 0.06410(14) 0.19455(11) 0.0170(4) Uani 1 1 d . . .
C2 C -0.10001(19) 0.14272(15) 0.22140(12) 0.0216(4) Uani 1 1 d . . .
C3 C -0.0977(2) 0.17479(18) 0.32473(14) 0.0351(5) Uani 1 1 d . . .
H3 H -0.1659 0.2275 0.3447 0.042 Uiso 1 1 calc R . .
C4 C 0.0017(2) 0.1315(2) 0.39848(14) 0.0406(6) Uani 1 1 d . . .
H4 H 0.0016 0.1545 0.4685 0.049 Uiso 1 1 calc R . .
C5 C 0.1013(2) 0.05465(17) 0.37055(13) 0.0327(5) Uani 1 1 d . . .
H5 H 0.1695 0.0255 0.4218 0.039 Uiso 1 1 calc R . .
C6 C 0.10386(19) 0.01909(15) 0.26842(12) 0.0203(4) Uani 1 1 d . . .
C7 C -0.21403(19) 0.19288(15) 0.14525(13) 0.0217(4) Uani 1 1 d . . .
H7 H -0.1984 0.1641 0.0750 0.026 Uiso 1 1 calc R . .
C8 C -0.2122(2) 0.32811(16) 0.14303(14) 0.0344(5) Uani 1 1 d . . .
H8A H -0.2292 0.3587 0.2108 0.052 Uiso 1 1 calc R . .
H8B H -0.2844 0.3565 0.0908 0.052 Uiso 1 1 calc R . .
H8C H -0.1218 0.3555 0.1261 0.052 Uiso 1 1 calc R . .
C9 C -0.3559(2) 0.14801(17) 0.16912(14) 0.0315(5) Uani 1 1 d . . .
H9A H -0.3546 0.0617 0.1726 0.047 Uiso 1 1 calc R . .
H9B H -0.4268 0.1735 0.1146 0.047 Uiso 1 1 calc R . .
H9C H -0.3770 0.1802 0.2354 0.047 Uiso 1 1 calc R . .
C10 C 0.21611(19) -0.06545(14) 0.24277(13) 0.0208(4) Uani 1 1 d . . .
H10 H 0.2010 -0.0827 0.1673 0.025 Uiso 1 1 calc R . .
C11 C 0.3607(2) -0.01191(17) 0.26595(15) 0.0317(5) Uani 1 1 d . . .
H11A H 0.3657 0.0621 0.2278 0.048 Uiso 1 1 calc R . .
H11B H 0.4298 -0.0672 0.2449 0.048 Uiso 1 1 calc R . .
H11C H 0.3791 0.0036 0.3400 0.048 Uiso 1 1 calc R . .
C12 C 0.2087(2) -0.18234(16) 0.30073(14) 0.0320(5) Uani 1 1 d . . .
H12A H 0.2283 -0.1683 0.3749 0.048 Uiso 1 1 calc R . .
H12B H 0.2771 -0.2373 0.2782 0.048 Uiso 1 1 calc R . .
H12C H 0.1160 -0.2161 0.2862 0.048 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 N1 1.7170(15) . ?
Si1 N1 1.7181(15) 3 ?
Si1 Cl1 2.0280(14) . ?
Si1 Cl2 2.0298(12) . ?
Si1 Si1 2.4704(14) 3 ?
N1 C1 1.447(2) . ?
N1 Si1 1.7181(15) 3 ?
C1 C2 1.401(2) . ?
C1 C6 1.408(2) . ?
C2 C3 1.395(2) . ?
C2 C7 1.519(2) . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(2) . ?
C5 H5 0.9500 . ?
C6 C10 1.517(2) . ?
C7 C9 1.534(3) . ?
C7 C8 1.534(3) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.533(3) . ?
C10 C12 1.532(2) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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
N1 Si1 N1 88.03(7) . 3 ?
N1 Si1 Cl1 116.20(6) . . ?
N1 Si1 Cl1 115.78(6) 3 . ?
N1 Si1 Cl2 115.80(5) . . ?
N1 Si1 Cl2 116.15(6) 3 . ?
Cl1 Si1 Cl2 104.95(3) . . ?
N1 Si1 Si1 44.03(5) . 3 ?
N1 Si1 Si1 44.00(5) 3 3 ?
Cl1 Si1 Si1 127.54(4) . 3 ?
Cl2 Si1 Si1 127.52(5) . 3 ?
C1 N1 Si1 133.70(11) . . ?
C1 N1 Si1 134.32(11) . 3 ?
Si1 N1 Si1 91.97(7) . 3 ?
C2 C1 C6 121.73(15) . . ?
C2 C1 N1 119.22(15) . . ?
C6 C1 N1 119.05(15) . . ?
C3 C2 C1 117.95(17) . . ?
C3 C2 C7 118.05(16) . . ?
C1 C2 C7 123.99(15) . . ?
C4 C3 C2 121.29(18) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.00(17) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 121.25(18) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 117.78(16) . . ?
C5 C6 C10 118.67(16) . . ?
C1 C6 C10 123.55(15) . . ?
C2 C7 C9 110.68(15) . . ?
C2 C7 C8 112.19(15) . . ?
C9 C7 C8 110.37(16) . . ?
C2 C7 H7 107.8 . . ?
C9 C7 H7 107.8 . . ?
C8 C7 H7 107.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 C11 111.91(15) . . ?
C6 C10 C12 111.42(15) . . ?
C11 C10 C12 109.63(15) . . ?
C6 C10 H10 107.9 . . ?
C11 C10 H10 107.9 . . ?
C12 C10 H10 107.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
N1 Si1 N1 C1 -179.27(19) 3 . . . ?
Cl1 Si1 N1 C1 62.83(16) . . . . ?
Cl2 Si1 N1 C1 -61.03(17) . . . . ?
Si1 Si1 N1 C1 -179.27(19) 3 . . . ?
N1 Si1 N1 Si1 0.0 3 . . 3 ?
Cl1 Si1 N1 Si1 -117.91(6) . . . 3 ?
Cl2 Si1 N1 Si1 118.24(7) . . . 3 ?
Si1 N1 C1 C2 89.9(2) . . . . ?
Si1 N1 C1 C2 -89.1(2) 3 . . . ?
Si1 N1 C1 C6 -89.9(2) . . . . ?
Si1 N1 C1 C6 91.1(2) 3 . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
N1 C1 C2 C3 179.49(16) . . . . ?
C6 C1 C2 C7 -179.24(16) . . . . ?
N1 C1 C2 C7 1.0(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C7 C2 C3 C4 179.15(19) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C5 C6 C10 179.97(18) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
N1 C1 C6 C5 -179.74(16) . . . . ?
C2 C1 C6 C10 -179.53(16) . . . . ?
N1 C1 C6 C10 0.3(2) . . . . ?
C3 C2 C7 C9 -64.6(2) . . . . ?
C1 C2 C7 C9 113.90(19) . . . . ?
C3 C2 C7 C8 59.1(2) . . . . ?
C1 C2 C7 C8 -122.34(19) . . . . ?
C5 C6 C10 C11 -62.7(2) . . . . ?
C1 C6 C10 C11 117.27(18) . . . . ?
C5 C6 C10 C12 60.4(2) . . . . ?
C1 C6 C10 C12 -119.58(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.91
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.062
####################################################################### 
# 
# 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 1418863'
_audit_update_record             
;
2015-10-26 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;
_audit_creation_date             2015-10-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H37 Cl2 N3 Si, C7 H8'
_chemical_formula_sum            'C30 H45 Cl2 N3 Si'
_chemical_formula_weight         546.68
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   9.490(4)
_cell_length_b                   14.842(6)
_cell_length_c                   21.882(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.321(7)
_cell_angle_gamma                90
_cell_volume                     3081(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9391
_cell_measurement_temperature    113
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.7
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.741
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            23056
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.007
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_min         1.658
_diffrn_ambient_temperature      113
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
scan:
	Number of images: 180
	           Slice: -110.0000 - 70.0000
	     Image width: 1.0000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 44.9835
	          2theta: -19.9948
scan:
	Number of images: 140
	           Slice: -110.0000 - 30.0000
	     Image width: 1.0000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 44.9835
	          2theta: -19.9948
scan:
	Number of images: 75
	           Slice: -110.0000 - -35.0000
	     Image width: 1.0000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 44.9835
	          2theta: -19.9948
;
_diffrn_measurement_device       
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.029407
_diffrn_orient_matrix_UB_12      0.066919
_diffrn_orient_matrix_UB_13      -0.075942
_diffrn_orient_matrix_UB_21      -0.061404
_diffrn_orient_matrix_UB_22      -0.027730
_diffrn_orient_matrix_UB_23      -0.000658
_diffrn_orient_matrix_UB_31      -0.014128
_diffrn_orient_matrix_UB_32      0.030551
_diffrn_orient_matrix_UB_33      0.030929
_diffrn_radiation_monochromator  Multilayer
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4578
_reflns_number_total             5427
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         5427
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0656
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0980P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1669
_refine_ls_wR_factor_ref         0.1781
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C31 \\sim C32 \\sim C33 \\sim C34 \\sim C35 \\sim C36 \\sim C37: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
C24 \\sim C25 \\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: C24(0.5) C25(0.5) H25(0.5) C26(0.5) H26(0.5) C27(0.5) H27(0.5)
 C28(0.5) H28(0.5) C29(0.5) H29(0.5) C30(0.5) H30A(0.5) H30B(0.5) H30C(0.5)
 C32(0.5) H32(0.5) C31(0.5) C36(0.5) H36(0.5) C35(0.5) H35(0.5) C34(0.5)
 H34(0.5) C33(0.5) H33(0.5) C37(0.5) H37A(0.5) H37B(0.5) H37C(0.5)
4.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10), C16(H16), C21(H21)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29),
 C32(H32), C36(H36), C35(H35), C34(H34), C33(H33)
4.c Fitted hexagon refined as free rotating group:
 C32(C31,C36,C35,C34,C33)
4.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C),
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C30(H30A,H30B,H30C), C37(H37A,
 H37B,H37C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.54325(8) 0.32630(6) 0.57043(3) 0.0328(2) Uani 1 1 d . . . . .
Cl2 Cl 0.55483(8) 0.18191(5) 0.68171(3) 0.0310(2) Uani 1 1 d . . . . .
Si1 Si 0.62636(8) 0.31154(6) 0.65963(4) 0.0216(2) Uani 1 1 d . . . . .
N1 N 0.5955(3) 0.38706(17) 0.70772(11) 0.0276(6) Uani 1 1 d . . . . .
N2 N 0.9279(3) 0.35402(17) 0.66694(10) 0.0237(6) Uani 1 1 d . . . . .
N3 N 0.8869(2) 0.23444(17) 0.61222(10) 0.0228(6) Uani 1 1 d . . . . .
C1 C 0.4991(3) 0.4400(2) 0.73799(13) 0.0240(7) Uani 1 1 d . . . . .
C2 C 0.4338(3) 0.4076(2) 0.79152(14) 0.0316(8) Uani 1 1 d . . . . .
C3 C 0.3348(3) 0.4620(3) 0.82010(15) 0.0376(9) Uani 1 1 d . . . . .
H3 H 0.2913 0.4408 0.8549 0.045 Uiso 1 1 calc R . . . .
C4 C 0.3001(4) 0.5463(3) 0.79803(15) 0.0429(10) Uani 1 1 d . . . . .
H4 H 0.2325 0.5808 0.8173 0.051 Uiso 1 1 calc R . . . .
C5 C 0.3660(4) 0.5788(2) 0.74737(16) 0.0401(9) Uani 1 1 d . . . . .
H5 H 0.3427 0.6359 0.7328 0.048 Uiso 1 1 calc R . . . .
C6 C 0.4673(3) 0.5282(2) 0.71722(14) 0.0287(7) Uani 1 1 d . . . . .
C7 C 0.5389(4) 0.5683(2) 0.66226(15) 0.0371(8) Uani 1 1 d . . . . .
H7 H 0.6142 0.5269 0.6507 0.045 Uiso 1 1 calc R . . . .
C8 C 0.6072(5) 0.6587(3) 0.6775(2) 0.0665(13) Uani 1 1 d . . . . .
H8A H 0.5354 0.7020 0.6863 0.100 Uiso 1 1 calc GR . . . .
H8B H 0.6602 0.6790 0.6433 0.100 Uiso 1 1 calc GR . . . .
H8C H 0.6692 0.6520 0.7125 0.100 Uiso 1 1 calc GR . . . .
C9 C 0.4380(4) 0.5773(3) 0.60752(16) 0.0489(10) Uani 1 1 d . . . . .
H9A H 0.4035 0.5187 0.5959 0.073 Uiso 1 1 calc GR . . . .
H9B H 0.4866 0.6036 0.5739 0.073 Uiso 1 1 calc GR . . . .
H9C H 0.3603 0.6151 0.6182 0.073 Uiso 1 1 calc GR . . . .
C10 C 0.4739(4) 0.3168(2) 0.81792(15) 0.0428(10) Uani 1 1 d . . . . .
H10 H 0.5143 0.2810 0.7850 0.051 Uiso 1 1 calc R . . . .
C11 C 0.5857(4) 0.3261(3) 0.8682(2) 0.0583(12) Uani 1 1 d . . . . .
H11A H 0.6658 0.3575 0.8526 0.087 Uiso 1 1 calc GR . . . .
H11B H 0.6142 0.2674 0.8820 0.087 Uiso 1 1 calc GR . . . .
H11C H 0.5480 0.3594 0.9017 0.087 Uiso 1 1 calc GR . . . .
C12 C 0.3485(5) 0.2643(3) 0.84255(19) 0.0697(14) Uani 1 1 d . . . . .
H12A H 0.3125 0.2949 0.8775 0.105 Uiso 1 1 calc GR . . . .
H12B H 0.3784 0.2048 0.8541 0.105 Uiso 1 1 calc GR . . . .
H12C H 0.2758 0.2602 0.8114 0.105 Uiso 1 1 calc GR . . . .
C13 C 0.8238(3) 0.2989(2) 0.64573(12) 0.0216(7) Uani 1 1 d . . . . .
C14 C 1.0577(3) 0.3223(2) 0.64786(14) 0.0288(8) Uani 1 1 d . . . . .
C15 C 1.0319(3) 0.2483(2) 0.61330(13) 0.0269(7) Uani 1 1 d . . . . .
C16 C 0.9049(3) 0.4361(2) 0.70493(13) 0.0273(7) Uani 1 1 d . . . . .
H16 H 0.8033 0.4481 0.7033 0.033 Uiso 1 1 calc R . . . .
C17 C 0.9765(4) 0.5192(2) 0.67859(15) 0.0396(9) Uani 1 1 d . . . . .
H17A H 1.0760 0.5164 0.6875 0.059 Uiso 1 1 calc GR . . . .
H17B H 0.9380 0.5725 0.6966 0.059 Uiso 1 1 calc GR . . . .
H17C H 0.9607 0.5208 0.6351 0.059 Uiso 1 1 calc GR . . . .
C18 C 0.9436(3) 0.4190(2) 0.77114(13) 0.0337(8) Uani 1 1 d . . . . .
H18A H 0.8940 0.3669 0.7852 0.051 Uiso 1 1 calc GR . . . .
H18B H 0.9183 0.4704 0.7952 0.051 Uiso 1 1 calc GR . . . .
H18C H 1.0433 0.4088 0.7752 0.051 Uiso 1 1 calc GR . . . .
C19 C 1.1966(3) 0.3639(3) 0.66329(16) 0.0412(9) Uani 1 1 d . . . . .
H19A H 1.2149 0.4118 0.6350 0.062 Uiso 1 1 calc GR . . . .
H19B H 1.2693 0.3192 0.6607 0.062 Uiso 1 1 calc GR . . . .
H19C H 1.1953 0.3877 0.7041 0.062 Uiso 1 1 calc GR . . . .
C20 C 1.1375(3) 0.1927(2) 0.57977(14) 0.0358(8) Uani 1 1 d . . . . .
H20A H 1.1152 0.1300 0.5840 0.054 Uiso 1 1 calc GR . . . .
H20B H 1.2302 0.2040 0.5966 0.054 Uiso 1 1 calc GR . . . .
H20C H 1.1347 0.2088 0.5373 0.054 Uiso 1 1 calc GR . . . .
C21 C 0.8114(3) 0.1587(2) 0.58146(14) 0.0294(7) Uani 1 1 d . . . . .
H21 H 0.7106 0.1699 0.5864 0.035 Uiso 1 1 calc R . . . .
C22 C 0.8360(4) 0.1567(3) 0.51331(15) 0.0518(11) Uani 1 1 d . . . . .
H22A H 0.8209 0.2158 0.4966 0.078 Uiso 1 1 calc GR . . . .
H22B H 0.7716 0.1151 0.4941 0.078 Uiso 1 1 calc GR . . . .
H22C H 0.9310 0.1381 0.5061 0.078 Uiso 1 1 calc GR . . . .
C23 C 0.8439(4) 0.0696(2) 0.61370(18) 0.0468(10) Uani 1 1 d . . . . .
H23A H 0.9426 0.0565 0.6110 0.070 Uiso 1 1 calc GR . . . .
H23B H 0.7902 0.0221 0.5945 0.070 Uiso 1 1 calc GR . . . .
H23C H 0.8193 0.0741 0.6559 0.070 Uiso 1 1 calc GR . . . .
C24 C 0.5111(17) -0.0675(10) 0.5254(5) 0.036(3) Uani 0.5 1 d . U P A -1
C25 C 0.4691(16) 0.0148(10) 0.5539(7) 0.036(4) Uani 0.5 1 d . U P A -1
H25 H 0.4533 0.0168 0.5957 0.044 Uiso 0.5 1 calc R . P A -1
C26 C 0.4527(16) 0.0897(11) 0.5190(7) 0.042(3) Uani 0.5 1 d . U P A -1
H26 H 0.4257 0.1432 0.5375 0.050 Uiso 0.5 1 calc R . P A -1
C27 C 0.4746(17) 0.0891(12) 0.4572(7) 0.046(3) Uani 0.5 1 d . U P A -1
H27 H 0.4592 0.1407 0.4339 0.055 Uiso 0.5 1 calc R . P A -1
C28 C 0.5189(18) 0.0125(11) 0.4314(7) 0.038(3) Uani 0.5 1 d . U P A -1
H28 H 0.5352 0.0123 0.3896 0.046 Uiso 0.5 1 calc R . P A -1
C29 C 0.5408(16) -0.0650(12) 0.4635(5) 0.032(3) Uani 0.5 1 d . U P A -1
H29 H 0.5755 -0.1159 0.4442 0.038 Uiso 0.5 1 calc R . P A -1
C30 C 0.5321(9) -0.1516(7) 0.5637(4) 0.057(2) Uani 0.5 1 d . U P A -1
H30A H 0.4701 -0.1982 0.5487 0.086 Uiso 0.5 1 calc GR . P A -1
H30B H 0.5113 -0.1386 0.6055 0.086 Uiso 0.5 1 calc GR . P A -1
H30C H 0.6280 -0.1715 0.5611 0.086 Uiso 0.5 1 calc GR . P A -1
C32 C -0.0924(5) 0.4354(4) 0.4965(3) 0.045(2) Uani 0.5 1 d . U P B -1
H32 H -0.1780 0.4052 0.4982 0.054 Uiso 0.5 1 calc R . P B -1
C31 C -0.0875(5) 0.5282(4) 0.5047(3) 0.051(2) Uani 0.5 1 d G U P B -1
C36 C 0.0405(8) 0.5734(4) 0.5023(3) 0.058(3) Uani 0.5 1 d G U P B -1
H36 H 0.0438 0.6355 0.5078 0.070 Uiso 0.5 1 calc R . P B -1
C35 C 0.1637(5) 0.5258(6) 0.4916(3) 0.070(3) Uani 0.5 1 d G U P B -1
H35 H 0.2493 0.5561 0.4899 0.084 Uiso 0.5 1 calc R . P B -1
C34 C 0.1588(6) 0.4330(6) 0.4834(3) 0.069(3) Uani 0.5 1 d G U P B -1
H34 H 0.2412 0.4011 0.4763 0.083 Uiso 0.5 1 calc R . P B -1
C33 C 0.0308(8) 0.3878(4) 0.4859(3) 0.057(2) Uani 0.5 1 d G U P B -1
H33 H 0.0275 0.3257 0.4804 0.068 Uiso 0.5 1 calc R . P B -1
C37 C -0.2233(13) 0.5750(9) 0.5166(6) 0.088(4) Uani 0.5 1 d . U P B -1
H37A H -0.2713 0.5876 0.4785 0.132 Uiso 0.5 1 calc GR . P B -1
H37B H -0.2047 0.6304 0.5379 0.132 Uiso 0.5 1 calc GR . P B -1
H37C H -0.2813 0.5370 0.5411 0.132 Uiso 0.5 1 calc GR . P B -1


_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 Si1 2.0997(13) . ?
Cl2 Si1 2.1002(14) . ?
Si1 N1 1.570(3) . ?
Si1 C13 1.914(3) . ?
N1 C1 1.385(4) . ?
N2 C13 1.356(4) . ?
N2 C14 1.391(4) . ?
N2 C16 1.493(4) . ?
N3 C13 1.354(4) . ?
N3 C15 1.391(4) . ?
N3 C21 1.486(4) . ?
C1 C2 1.422(4) . ?
C1 C6 1.416(4) . ?
C2 C3 1.397(4) . ?
C2 C10 1.511(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.398(4) . ?
C6 C7 1.517(5) . ?
C7 H7 0.9800 . ?
C7 C8 1.523(5) . ?
C7 C9 1.522(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10 0.9800 . ?
C10 C11 1.517(5) . ?
C10 C12 1.531(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 C15 1.353(4) . ?
C14 C19 1.488(4) . ?
C15 C20 1.502(4) . ?
C16 H16 0.9800 . ?
C16 C17 1.528(4) . ?
C16 C18 1.508(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21 0.9800 . ?
C21 C22 1.515(4) . ?
C21 C23 1.527(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.431(16) . ?
C24 C29 1.391(15) . ?
C24 C30 1.514(13) . ?
C25 H25 0.9300 . ?
C25 C26 1.355(15) . ?
C26 H26 0.9300 . ?
C26 C27 1.373(17) . ?
C27 H27 0.9300 . ?
C27 C28 1.342(17) . ?
C28 H28 0.9300 . ?
C28 C29 1.361(13) . ?
C29 H29 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C32 H32 0.9300 . ?
C32 C31 1.3900 . ?
C32 C33 1.3900 . ?
C31 C36 1.3900 . ?
C31 C37 1.492(12) . ?
C36 H36 0.9300 . ?
C36 C35 1.3900 . ?
C35 H35 0.9300 . ?
C35 C34 1.3900 . ?
C34 H34 0.9300 . ?
C34 C33 1.3900 . ?
C33 H33 0.9300 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 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
Cl1 Si1 Cl2 101.13(5) . . ?
N1 Si1 Cl1 118.47(11) . . ?
N1 Si1 Cl2 115.69(10) . . ?
N1 Si1 C13 112.03(13) . . ?
C13 Si1 Cl1 102.16(9) . . ?
C13 Si1 Cl2 105.64(10) . . ?
C1 N1 Si1 149.4(2) . . ?
C13 N2 C14 109.6(3) . . ?
C13 N2 C16 124.6(2) . . ?
C14 N2 C16 125.8(2) . . ?
C13 N3 C15 109.7(2) . . ?
C13 N3 C21 124.4(2) . . ?
C15 N3 C21 125.8(2) . . ?
N1 C1 C2 120.5(3) . . ?
N1 C1 C6 120.6(3) . . ?
C6 C1 C2 118.9(3) . . ?
C1 C2 C10 120.4(3) . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 C10 120.6(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.7(3) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.5(3) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C7 121.4(3) . . ?
C5 C6 C1 119.3(3) . . ?
C5 C6 C7 119.3(3) . . ?
C6 C7 H7 107.5 . . ?
C6 C7 C8 111.6(3) . . ?
C6 C7 C9 111.9(3) . . ?
C8 C7 H7 107.5 . . ?
C9 C7 H7 107.5 . . ?
C9 C7 C8 110.6(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 H10 107.6 . . ?
C2 C10 C11 111.2(3) . . ?
C2 C10 C12 113.5(3) . . ?
C11 C10 H10 107.6 . . ?
C11 C10 C12 109.1(3) . . ?
C12 C10 H10 107.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 Si1 126.5(2) . . ?
N3 C13 Si1 127.0(2) . . ?
N3 C13 N2 106.5(2) . . ?
N2 C14 C19 125.2(3) . . ?
C15 C14 N2 107.0(3) . . ?
C15 C14 C19 127.7(3) . . ?
N3 C15 C20 125.6(3) . . ?
C14 C15 N3 107.2(2) . . ?
C14 C15 C20 127.2(3) . . ?
N2 C16 H16 106.5 . . ?
N2 C16 C17 112.1(2) . . ?
N2 C16 C18 111.2(2) . . ?
C17 C16 H16 106.5 . . ?
C18 C16 H16 106.5 . . ?
C18 C16 C17 113.4(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C21 H21 106.5 . . ?
N3 C21 C22 112.1(3) . . ?
N3 C21 C23 110.9(3) . . ?
C22 C21 H21 106.5 . . ?
C22 C21 C23 113.9(3) . . ?
C23 C21 H21 106.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C30 119.8(10) . . ?
C29 C24 C25 117.7(9) . . ?
C29 C24 C30 122.3(10) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 C24 119.0(11) . . ?
C26 C25 H25 120.5 . . ?
C25 C26 H26 119.0 . . ?
C25 C26 C27 122.1(12) . . ?
C27 C26 H26 119.0 . . ?
C26 C27 H27 120.8 . . ?
C28 C27 C26 118.5(11) . . ?
C28 C27 H27 120.8 . . ?
C27 C28 H28 118.5 . . ?
C27 C28 C29 122.9(12) . . ?
C29 C28 H28 118.5 . . ?
C24 C29 H29 120.2 . . ?
C28 C29 C24 119.6(12) . . ?
C28 C29 H29 120.2 . . ?
C24 C30 H30A 109.5 . . ?
C24 C30 H30B 109.5 . . ?
C24 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C31 C32 H32 120.0 . . ?
C31 C32 C33 120.0 . . ?
C33 C32 H32 120.0 . . ?
C32 C31 C36 120.0 . . ?
C32 C31 C37 117.2(8) . . ?
C36 C31 C37 122.8(8) . . ?
C31 C36 H36 120.0 . . ?
C31 C36 C35 120.0 . . ?
C35 C36 H36 120.0 . . ?
C36 C35 H35 120.0 . . ?
C34 C35 C36 120.0 . . ?
C34 C35 H35 120.0 . . ?
C35 C34 H34 120.0 . . ?
C35 C34 C33 120.0 . . ?
C33 C34 H34 120.0 . . ?
C32 C33 H33 120.0 . . ?
C34 C33 C32 120.0 . . ?
C34 C33 H33 120.0 . . ?
C31 C37 H37A 109.5 . . ?
C31 C37 H37B 109.5 . . ?
C31 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?

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
Cl1 Si1 N1 C1 54.0(5) . . . . ?
Cl2 Si1 N1 C1 -66.3(5) . . . . ?
Si1 N1 C1 C2 85.6(5) . . . . ?
Si1 N1 C1 C6 -96.4(5) . . . . ?
N1 C1 C2 C3 -178.6(3) . . . . ?
N1 C1 C2 C10 3.0(4) . . . . ?
N1 C1 C6 C5 177.7(3) . . . . ?
N1 C1 C6 C7 -1.2(4) . . . . ?
N2 C14 C15 N3 -0.9(3) . . . . ?
N2 C14 C15 C20 176.7(3) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C1 C2 C10 C11 95.2(4) . . . . ?
C1 C2 C10 C12 -141.4(3) . . . . ?
C1 C6 C7 C8 -125.9(3) . . . . ?
C1 C6 C7 C9 109.5(3) . . . . ?
C2 C1 C6 C5 -4.1(4) . . . . ?
C2 C1 C6 C7 176.9(3) . . . . ?
C2 C3 C4 C5 -1.3(5) . . . . ?
C3 C2 C10 C11 -83.2(4) . . . . ?
C3 C2 C10 C12 40.2(4) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C4 C5 C6 C1 2.3(5) . . . . ?
C4 C5 C6 C7 -178.7(3) . . . . ?
C5 C6 C7 C8 55.2(4) . . . . ?
C5 C6 C7 C9 -69.4(4) . . . . ?
C6 C1 C2 C3 3.3(4) . . . . ?
C6 C1 C2 C10 -175.1(3) . . . . ?
C10 C2 C3 C4 177.8(3) . . . . ?
C13 Si1 N1 C1 172.5(4) . . . . ?
C13 N2 C14 C15 1.6(3) . . . . ?
C13 N2 C14 C19 -178.7(3) . . . . ?
C13 N2 C16 C17 -128.2(3) . . . . ?
C13 N2 C16 C18 103.7(3) . . . . ?
C13 N3 C15 C14 -0.1(3) . . . . ?
C13 N3 C15 C20 -177.7(3) . . . . ?
C13 N3 C21 C22 122.8(3) . . . . ?
C13 N3 C21 C23 -108.7(3) . . . . ?
C14 N2 C13 Si1 179.3(2) . . . . ?
C14 N2 C13 N3 -1.6(3) . . . . ?
C14 N2 C16 C17 51.8(4) . . . . ?
C14 N2 C16 C18 -76.3(3) . . . . ?
C15 N3 C13 Si1 -179.9(2) . . . . ?
C15 N3 C13 N2 1.1(3) . . . . ?
C15 N3 C21 C22 -60.0(4) . . . . ?
C15 N3 C21 C23 68.5(4) . . . . ?
C16 N2 C13 Si1 -0.7(4) . . . . ?
C16 N2 C13 N3 178.4(2) . . . . ?
C16 N2 C14 C15 -178.4(3) . . . . ?
C16 N2 C14 C19 1.3(5) . . . . ?
C19 C14 C15 N3 179.4(3) . . . . ?
C19 C14 C15 C20 -3.0(5) . . . . ?
C21 N3 C13 Si1 -2.2(4) . . . . ?
C21 N3 C13 N2 178.7(3) . . . . ?
C21 N3 C15 C14 -177.7(3) . . . . ?
C21 N3 C15 C20 4.7(5) . . . . ?
C24 C25 C26 C27 0.2(18) . . . . ?
C25 C24 C29 C28 -5.1(17) . . . . ?
C25 C26 C27 C28 -2.6(18) . . . . ?
C26 C27 C28 C29 1.0(18) . . . . ?
C27 C28 C29 C24 2.8(19) . . . . ?
C29 C24 C25 C26 3.6(17) . . . . ?
C30 C24 C25 C26 179.1(12) . . . . ?
C30 C24 C29 C28 179.5(12) . . . . ?
C32 C31 C36 C35 0.0 . . . . ?
C31 C32 C33 C34 0.0 . . . . ?
C31 C36 C35 C34 0.0 . . . . ?
C36 C35 C34 C33 0.0 . . . . ?
C35 C34 C33 C32 0.0 . . . . ?
C33 C32 C31 C36 0.0 . . . . ?
C33 C32 C31 C37 -179.4(8) . . . . ?
C37 C31 C36 C35 179.3(9) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
