# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1843653'
_audit_update_record             
;
2018-05-16 deposited with the CCDC.
2018-07-12 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C8 H19 N3 Si2'
_chemical_formula_sum            'C8 H19 N3 Si2'
_chemical_formula_iupac          ?
_chemical_formula_weight         213.44

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.7038(11)
_cell_length_b                   9.1027(15)
_cell_length_c                   21.146(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.335(2)
_cell_angle_gamma                90
_cell_volume                     1290.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9881
_cell_measurement_theta_min      2.4361
_cell_measurement_theta_max      30.5048
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.099
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464

_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5 (Bruker AXS, 2014)'
_exptl_absorpt_correction_T_min  0.6150
_exptl_absorpt_correction_T_max  0.7461

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'

_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega- and phi-scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            24848
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27

_refine_special_details          
;
;

_reflns_number_total             2950
_reflns_number_gt                2747
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0655
_refine_ls_wR_factor_gt          0.1652
_refine_ls_wR_factor_ref         0.1665
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_number_reflns         2950
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0196P)²+8.9477P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.013
_refine_diff_density_min         -0.440
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       
'Bruker Instrument Service v2012.12.0.3 (Bruker AXS, 2012)'
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS, 2013)'
_computing_structure_solution    'SHELXTL XT 2014/4 (Bruker AXS, 2014)'
_computing_structure_refinement  'SHELXTL XL 2014/7 (Bruker AXS, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXTL XT 2014/4 (Bruker AXS, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2110(5) 0.4450(4) 0.31923(15) 0.0138(6) Uani d . . . 1 . .
C C2 0.1427(5) 0.3044(4) 0.33422(15) 0.0142(6) Uani d . . . 1 . .
C C3 0.4891(6) 0.6983(4) 0.28970(18) 0.0243(8) Uani d . . . 1 . .
H H3A 0.3745 0.7554 0.2739 0.036 Uiso calc U . R 1 . .
H H3B 0.5433 0.6402 0.2551 0.036 Uiso calc U . R 1 . .
H H3C 0.5922 0.7652 0.3063 0.036 Uiso calc U . R 1 . .
C C4 0.6305(5) 0.4662(4) 0.38266(18) 0.0212(7) Uani d . . . 1 . .
H H4A 0.679 0.4045 0.3483 0.032 Uiso calc U . R 1 . .
H H4B 0.5929 0.4038 0.4182 0.032 Uiso calc U . R 1 . .
H H4C 0.7361 0.5341 0.3965 0.032 Uiso calc U . R 1 . .
C C5 0.2896(5) 0.6781(4) 0.41912(18) 0.0231(8) Uani d . . . 1 . .
H H5A 0.3872 0.7461 0.4381 0.035 Uiso calc U . R 1 . .
H H5B 0.244 0.6095 0.4515 0.035 Uiso calc U . R 1 . .
H H5C 0.1754 0.7337 0.402 0.035 Uiso calc U . R 1 . .
C C6 0.4367(5) 0.0747(5) 0.3876(2) 0.0284(9) Uani d . . . 1 . .
H H6A 0.4791 0.023 0.4263 0.043 Uiso calc U . R 1 . .
H H6B 0.5403 0.1446 0.3756 0.043 Uiso calc U . R 1 . .
H H6C 0.4151 0.0033 0.3534 0.043 Uiso calc U . R 1 . .
C C7 -0.0104(5) 0.0423(4) 0.40789(18) 0.0224(8) Uani d . . . 1 . .
H H7A -0.0263 -0.0115 0.3679 0.034 Uiso calc U . R 1 . .
H H7B -0.1339 0.0953 0.4166 0.034 Uiso calc U . R 1 . .
H H7C 0.0189 -0.0272 0.4423 0.034 Uiso calc U . R 1 . .
C C8 0.2153(6) 0.2828(5) 0.47743(17) 0.0251(8) Uani d . . . 1 . .
H H8A 0.0928 0.3401 0.4822 0.038 Uiso calc U . R 1 . .
H H8B 0.3301 0.3493 0.4764 0.038 Uiso calc U . R 1 . .
H H8C 0.2315 0.2149 0.5132 0.038 Uiso calc U . R 1 . .
N N1 -0.0009(4) 0.2661(3) 0.28901(13) 0.0152(6) Uani d . . . 1 . .
N N2 -0.0242(4) 0.3748(3) 0.24813(14) 0.0179(6) Uani d . . . 1 . .
N N3 0.1021(4) 0.4815(3) 0.26633(14) 0.0162(6) Uani d . . . 1 . .
H H1 0.092(6) 0.566(5) 0.248(2) 0.019 Uiso d U . . 1 . .
Si Si1 0.40812(13) 0.57308(11) 0.35394(4) 0.0144(2) Uani d . . . 1 . .
Si Si2 0.19919(13) 0.17573(11) 0.40184(4) 0.0148(2) Uani d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N3 . 1.363(4) ?
C1 C2 . 1.398(5) ?
C1 Si1 . 1.897(3) ?
C2 N1 . 1.385(4) ?
C2 Si2 . 1.880(3) ?
C3 Si1 . 1.864(4) ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C3 H3C . 0.98 ?
C4 Si1 . 1.870(4) ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C4 H4C . 0.98 ?
C5 Si1 . 1.870(4) ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C5 H5C . 0.98 ?
C6 Si2 . 1.869(4) ?
C6 H6A . 0.98 ?
C6 H6B . 0.98 ?
C6 H6C . 0.98 ?
C7 Si2 . 1.864(4) ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
C7 H7C . 0.98 ?
C8 Si2 . 1.873(4) ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
N1 N2 . 1.321(4) ?
N2 N3 . 1.339(4) ?
N3 H1 . 0.86(5) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 C1 C2 . . 103.7(3) ?
N3 C1 Si1 . . 121.5(3) ?
C2 C1 Si1 . . 134.7(3) ?
N1 C2 C1 . . 107.5(3) ?
N1 C2 Si2 . . 119.5(2) ?
C1 C2 Si2 . . 132.9(3) ?
Si1 C3 H3A . . 109.5 ?
Si1 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
Si1 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
Si1 C4 H4A . . 109.5 ?
Si1 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
Si1 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
Si1 C5 H5A . . 109.5 ?
Si1 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
Si1 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
Si2 C6 H6A . . 109.5 ?
Si2 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
Si2 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
Si2 C7 H7A . . 109.5 ?
Si2 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
Si2 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
Si2 C8 H8A . . 109.5 ?
Si2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
Si2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N2 N1 C2 . . 109.4(3) ?
N1 N2 N3 . . 106.9(3) ?
N2 N3 C1 . . 112.5(3) ?
N2 N3 H1 . . 118.(3) ?
C1 N3 H1 . . 128.(3) ?
C3 Si1 C5 . . 111.13(18) ?
C3 Si1 C4 . . 108.15(17) ?
C5 Si1 C4 . . 112.09(17) ?
C3 Si1 C1 . . 107.82(16) ?
C5 Si1 C1 . . 107.18(16) ?
C4 Si1 C1 . . 110.39(16) ?
C7 Si2 C6 . . 109.66(19) ?
C7 Si2 C8 . . 108.01(18) ?
C6 Si2 C8 . . 111.16(19) ?
C7 Si2 C2 . . 108.62(16) ?
C6 Si2 C2 . . 109.96(16) ?
C8 Si2 C2 . . 109.37(17) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N3 C1 C2 N1 . . . . 0.5(3) ?
Si1 C1 C2 N1 . . . . -177.5(3) ?
N3 C1 C2 Si2 . . . . -176.0(3) ?
Si1 C1 C2 Si2 . . . . 6.0(5) ?
C1 C2 N1 N2 . . . . -0.4(4) ?
Si2 C2 N1 N2 . . . . 176.6(2) ?
C2 N1 N2 N3 . . . . 0.1(4) ?
N1 N2 N3 C1 . . . . 0.2(4) ?
C2 C1 N3 N2 . . . . -0.5(4) ?
Si1 C1 N3 N2 . . . . 177.9(2) ?
N3 C1 Si1 C3 . . . . -22.9(3) ?
C2 C1 Si1 C3 . . . . 154.9(3) ?
N3 C1 Si1 C5 . . . . 96.9(3) ?
C2 C1 Si1 C5 . . . . -85.4(4) ?
N3 C1 Si1 C4 . . . . -140.8(3) ?
C2 C1 Si1 C4 . . . . 36.9(4) ?
N1 C2 Si2 C7 . . . . -17.5(3) ?
C1 C2 Si2 C7 . . . . 158.7(3) ?
N1 C2 Si2 C6 . . . . 102.6(3) ?
C1 C2 Si2 C6 . . . . -81.3(4) ?
N1 C2 Si2 C8 . . . . -135.1(3) ?
C1 C2 Si2 C8 . . . . 41.0(4) ?

