# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_mo_SMYY007_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1543755'
_audit_update_record             
;
2017-04-12 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ' C16 H27 Cl1 N2 Si1'
_chemical_formula_sum            'C16 H27 Cl N2 Si'
_chemical_formula_weight         310.93

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.4858(18)
_cell_length_b                   11.987(2)
_cell_length_c                   15.459(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1757.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9970
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      27.28

_exptl_crystal_description       neeedle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.279
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_process_details   'SADABS (BRUKER, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50112
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  0.0918
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.519
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3099
_reflns_number_gt                2891
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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.
;

_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-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1015P)²+3.9023P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.053(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1156 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.31(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3099
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0646
_refine_ls_wR_factor_ref         0.1896
_refine_ls_wR_factor_gt          0.1840
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_restrained_S_all      1.151
_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_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 1.01697(14) 0.95386(11) 0.30665(9) 0.0148(4) Uani 1 1 d . . . . .
Si1 Si 0.8947(2) 0.78494(17) 0.33145(12) 0.0284(6) Uani 1 1 d . . . . .
N003 N 0.7585(7) 0.6628(5) 0.3395(4) 0.0296(14) Uani 1 1 d . . . . .
N004 N 0.8000(7) 0.7696(5) 0.2301(4) 0.0282(14) Uani 1 1 d . . . . .
C2 C 0.5857(8) 0.6456(6) 0.2185(4) 0.0289(16) Uani 1 1 d . . . . .
C7 C 0.4695(8) 0.7155(7) 0.2134(5) 0.0319(16) Uani 1 1 d . . . . .
H7 H 0.4738 0.7870 0.2365 0.038 Uiso 1 1 calc R U . . .
C1 C 0.7139(8) 0.6883(6) 0.2614(5) 0.0270(16) Uani 1 1 d . . . . .
C3 C 0.5777(8) 0.5391(6) 0.1837(5) 0.0320(16) Uani 1 1 d . . . . .
H3 H 0.6556 0.4922 0.1864 0.038 Uiso 1 1 calc R U . . .
C12 C 0.6871(9) 0.6026(7) 0.4093(5) 0.0326(17) Uani 1 1 d . . . . .
C8 C 0.8199(8) 0.8084(7) 0.1394(5) 0.0310(17) Uani 1 1 d . . . . .
C6 C 0.3466(8) 0.6786(7) 0.1737(5) 0.0362(19) Uani 1 1 d . . . . .
H6 H 0.2693 0.7260 0.1692 0.043 Uiso 1 1 calc R U . . .
C13 C 0.5461(9) 0.6570(8) 0.4312(5) 0.041(2) Uani 1 1 d . . . . .
H13A H 0.5621 0.7312 0.4523 0.061 Uiso 1 1 calc R U . . .
H13B H 0.4991 0.6139 0.4748 0.061 Uiso 1 1 calc R U . . .
H13C H 0.4885 0.6601 0.3802 0.061 Uiso 1 1 calc R U . . .
C9 C 0.7665(9) 0.9255(7) 0.1322(5) 0.0382(19) Uani 1 1 d . . . . .
H9A H 0.6697 0.9282 0.1503 0.057 Uiso 1 1 calc R U . . .
H9B H 0.7735 0.9500 0.0732 0.057 Uiso 1 1 calc R U . . .
H9C H 0.8219 0.9735 0.1684 0.057 Uiso 1 1 calc R U . . .
C16 C 1.0567(8) 0.7012(7) 0.3473(5) 0.0330(17) Uani 1 1 d . . . . .
H16A H 1.0436 0.6284 0.3226 0.049 Uiso 1 1 calc R U . . .
H16B H 1.0758 0.6942 0.4080 0.049 Uiso 1 1 calc R U . . .
H16C H 1.1346 0.7375 0.3194 0.049 Uiso 1 1 calc R U . . .
C4 C 0.4568(9) 0.5028(7) 0.1456(5) 0.0366(19) Uani 1 1 d . . . . .
H4 H 0.4527 0.4312 0.1225 0.044 Uiso 1 1 calc R U . . .
C5 C 0.3391(9) 0.5719(7) 0.1408(5) 0.0367(19) Uani 1 1 d . . . . .
H5 H 0.2561 0.5462 0.1157 0.044 Uiso 1 1 calc R U . . .
C14 C 0.6620(9) 0.4806(7) 0.3855(6) 0.0385(19) Uani 1 1 d . . . . .
H14A H 0.5923 0.4763 0.3407 0.058 Uiso 1 1 calc R U . . .
H14B H 0.6294 0.4408 0.4356 0.058 Uiso 1 1 calc R U . . .
H14C H 0.7485 0.4481 0.3655 0.058 Uiso 1 1 calc R U . . .
C10 C 0.7447(10) 0.7343(8) 0.0729(5) 0.042(2) Uani 1 1 d . . . . .
H10A H 0.7815 0.6599 0.0762 0.063 Uiso 1 1 calc R U . . .
H10B H 0.7601 0.7636 0.0159 0.063 Uiso 1 1 calc R U . . .
H10C H 0.6455 0.7332 0.0851 0.063 Uiso 1 1 calc R U . . .
C15 C 0.7822(10) 0.6074(8) 0.4867(5) 0.045(2) Uani 1 1 d . . . . .
H15A H 0.8653 0.5638 0.4759 0.067 Uiso 1 1 calc R U . . .
H15B H 0.7336 0.5779 0.5362 0.067 Uiso 1 1 calc R U . . .
H15C H 0.8085 0.6834 0.4977 0.067 Uiso 1 1 calc R U . . .
C11 C 0.9756(9) 0.8007(8) 0.1183(5) 0.044(2) Uani 1 1 d . . . . .
H11A H 1.0265 0.8546 0.1519 0.066 Uiso 1 1 calc R U . . .
H11B H 0.9896 0.8153 0.0579 0.066 Uiso 1 1 calc R U . . .
H11C H 1.0092 0.7272 0.1318 0.066 Uiso 1 1 calc R U . . .
H1 H 0.830(7) 0.845(6) 0.394(5) 0.019(18) 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 Si1 2.365(2) . ?
Si1 N004 1.815(6) . ?
Si1 C16 1.851(8) . ?
Si1 N003 1.957(7) . ?
Si1 C1 2.336(8) . ?
Si1 H1 1.35(7) . ?
N003 C1 1.315(9) . ?
N003 C12 1.465(10) . ?
N004 C1 1.360(10) . ?
N004 C8 1.490(10) . ?
C2 C7 1.387(11) . ?
C2 C3 1.387(10) . ?
C2 C1 1.477(10) . ?
C7 C6 1.390(11) . ?
C7 H7 0.9300 . ?
C3 C4 1.361(11) . ?
C3 H3 0.9300 . ?
C12 C15 1.500(11) . ?
C12 C13 1.526(11) . ?
C12 C14 1.526(11) . ?
C8 C9 1.497(12) . ?
C8 C11 1.514(11) . ?
C8 C10 1.534(11) . ?
C6 C5 1.378(12) . ?
C6 H6 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C4 C5 1.391(12) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
N004 Si1 C16 118.0(3) . . ?
N004 Si1 N003 69.6(3) . . ?
C16 Si1 N003 97.7(3) . . ?
N004 Si1 C1 35.5(3) . . ?
C16 Si1 C1 113.7(3) . . ?
N003 Si1 C1 34.3(3) . . ?
N004 Si1 Cl1 100.9(2) . . ?
C16 Si1 Cl1 94.5(3) . . ?
N003 Si1 Cl1 167.1(2) . . ?
C1 Si1 Cl1 135.2(2) . . ?
N004 Si1 H1 116(3) . . ?
C16 Si1 H1 125(3) . . ?
N003 Si1 H1 93(3) . . ?
C1 Si1 H1 105(3) . . ?
Cl1 Si1 H1 83(3) . . ?
C1 N003 C12 129.9(7) . . ?
C1 N003 Si1 88.9(5) . . ?
C12 N003 Si1 136.2(5) . . ?
C1 N004 C8 129.4(6) . . ?
C1 N004 Si1 93.6(5) . . ?
C8 N004 Si1 135.9(5) . . ?
C7 C2 C3 119.4(7) . . ?
C7 C2 C1 118.0(7) . . ?
C3 C2 C1 122.6(7) . . ?
C2 C7 C6 120.0(7) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
N003 C1 N004 107.4(7) . . ?
N003 C1 C2 126.6(7) . . ?
N004 C1 C2 125.7(7) . . ?
N003 C1 Si1 56.9(4) . . ?
N004 C1 Si1 50.9(4) . . ?
C2 C1 Si1 170.0(5) . . ?
C4 C3 C2 120.5(7) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
N003 C12 C15 106.9(7) . . ?
N003 C12 C13 111.0(6) . . ?
C15 C12 C13 109.5(7) . . ?
N003 C12 C14 111.5(7) . . ?
C15 C12 C14 108.8(7) . . ?
C13 C12 C14 109.0(7) . . ?
N004 C8 C9 108.6(6) . . ?
N004 C8 C11 107.9(7) . . ?
C9 C8 C11 111.8(7) . . ?
N004 C8 C10 113.0(6) . . ?
C9 C8 C10 109.6(7) . . ?
C11 C8 C10 105.9(7) . . ?
C5 C6 C7 120.1(8) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
Si1 C16 H16A 109.5 . . ?
Si1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
Si1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C3 C4 C5 120.6(7) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 119.4(7) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_refine_diff_density_max         1.366
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.116
_vrf_PLAT340_mo_SMYY007_0m_a     
;
Problem:Low Bond Precision on  C-C Bonds .... 0.01146 Ang
RESPONSE:This alert is generated because there is a disorder
in the structure.
;
# end Validation Reply Form


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
_chemical_properties_physical    ', Air-sensitive'
####################################################################### 
# 
# 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_mo_SEN_109_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1543756'
_audit_update_record             
;
2017-04-12 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          389.4
_chemical_formula_moiety         'C17 H29 Si1 N3'
_chemical_formula_sum            'C17 H27 N3 Si'
_chemical_formula_weight         301.50

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.527(3)
_cell_length_b                   12.162(4)
_cell_length_c                   15.346(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1778.0(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4461
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      19.66

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   0.959
_exptl_transmission_factor_max   0.972
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.131
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (BRUKER, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48296
_diffrn_reflns_av_unetI/netI     0.1655
_diffrn_reflns_av_R_equivalents  0.3217
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.137
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3132
_reflns_number_gt                1718
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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.
;

_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-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0642P)²+0.3115P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 517 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.33(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3132
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1731
_refine_ls_R_factor_gt           0.0668
_refine_ls_wR_factor_ref         0.1514
_refine_ls_wR_factor_gt          0.1147
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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_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
Si1 Si 0.88320(19) 0.22577(17) 0.33456(12) 0.0305(6) Uani 1 1 d . . . . .
N2 N 0.7873(5) 0.2377(4) 0.2338(3) 0.0261(14) Uani 1 1 d . . . . .
N1 N 0.7424(5) 0.3440(4) 0.3420(3) 0.0286(14) Uani 1 1 d . . . . .
C1 C 0.7001(7) 0.3193(6) 0.2637(4) 0.0260(17) Uani 1 1 d . . . . .
C2 C 0.5722(7) 0.3607(6) 0.2179(4) 0.0270(18) Uani 1 1 d . . . . .
C12 C 0.8098(7) 0.1972(6) 0.1438(4) 0.0297(18) Uani 1 1 d . . . . .
C7 C 0.4561(7) 0.2950(6) 0.2149(4) 0.0327(19) Uani 1 1 d . . . . .
H7 H 0.4586 0.2255 0.2402 0.039 Uiso 1 1 calc R U . . .
N3 N 1.0590(7) 0.0144(6) 0.3089(4) 0.058(2) Uani 1 1 d . . . . .
C3 C 0.5707(7) 0.4644(6) 0.1804(4) 0.0325(19) Uani 1 1 d . . . . .
H3 H 0.6500 0.5090 0.1818 0.039 Uiso 1 1 calc R U . . .
C8 C 0.6720(7) 0.4091(6) 0.4097(4) 0.0327(19) Uani 1 1 d . . . . .
C4 C 0.4481(8) 0.4999(7) 0.1408(4) 0.039(2) Uani 1 1 d . . . . .
H4 H 0.4449 0.5698 0.1162 0.046 Uiso 1 1 calc R U . . .
C17 C 1.0392(7) 0.3126(6) 0.3529(5) 0.041(2) Uani 1 1 d . . . . .
H17A H 1.1222 0.2679 0.3505 0.061 Uiso 1 1 calc R U . . .
H17B H 1.0328 0.3469 0.4091 0.061 Uiso 1 1 calc R U . . .
H17C H 1.0439 0.3683 0.3086 0.061 Uiso 1 1 calc R U . . .
C16 C 0.9907(7) 0.0921(7) 0.3092(5) 0.037(2) Uani 1 1 d . . . . .
C6 C 0.3344(7) 0.3312(7) 0.1742(5) 0.041(2) Uani 1 1 d . . . . .
H6 H 0.2555 0.2863 0.1720 0.049 Uiso 1 1 calc R U . . .
C10 C 0.6613(8) 0.5293(6) 0.3846(5) 0.048(2) Uani 1 1 d . . . . .
H10A H 0.7502 0.5542 0.3629 0.072 Uiso 1 1 calc R U . . .
H10B H 0.6355 0.5718 0.4348 0.072 Uiso 1 1 calc R U . . .
H10C H 0.5912 0.5380 0.3402 0.072 Uiso 1 1 calc R U . . .
C5 C 0.3319(8) 0.4342(7) 0.1373(5) 0.043(2) Uani 1 1 d . . . . .
H5 H 0.2509 0.4592 0.1098 0.051 Uiso 1 1 calc R U . . .
C14 C 0.7653(8) 0.0782(6) 0.1405(5) 0.045(2) Uani 1 1 d . . . . .
H14A H 0.8155 0.0373 0.1840 0.068 Uiso 1 1 calc R U . . .
H14B H 0.7859 0.0485 0.0840 0.068 Uiso 1 1 calc R U . . .
H14C H 0.6664 0.0729 0.1515 0.068 Uiso 1 1 calc R U . . .
C15 C 0.9645(7) 0.2101(7) 0.1218(4) 0.046(2) Uani 1 1 d . . . . .
H15A H 0.9898 0.2864 0.1245 0.069 Uiso 1 1 calc R U . . .
H15B H 0.9814 0.1828 0.0640 0.069 Uiso 1 1 calc R U . . .
H15C H 1.0198 0.1693 0.1628 0.069 Uiso 1 1 calc R U . . .
C11 C 0.5259(7) 0.3631(7) 0.4305(5) 0.046(2) Uani 1 1 d . . . . .
H11A H 0.4655 0.3730 0.3811 0.069 Uiso 1 1 calc R U . . .
H11B H 0.4875 0.4013 0.4798 0.069 Uiso 1 1 calc R U . . .
H11C H 0.5333 0.2861 0.4438 0.069 Uiso 1 1 calc R U . . .
C9 C 0.7640(9) 0.4003(6) 0.4903(4) 0.057(3) Uani 1 1 d . . . . .
H9A H 0.7759 0.3243 0.5055 0.086 Uiso 1 1 calc R U . . .
H9B H 0.7202 0.4385 0.5378 0.086 Uiso 1 1 calc R U . . .
H9C H 0.8540 0.4325 0.4785 0.086 Uiso 1 1 calc R U . . .
C13 C 0.7275(7) 0.2625(6) 0.0746(4) 0.045(2) Uani 1 1 d . . . . .
H13A H 0.6288 0.2496 0.0819 0.068 Uiso 1 1 calc R U . . .
H13B H 0.7558 0.2390 0.0175 0.068 Uiso 1 1 calc R U . . .
H13C H 0.7467 0.3395 0.0812 0.068 Uiso 1 1 calc R U . . .
H1 H 0.813(4) 0.170(4) 0.410(3) 0.001(12) 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 N2 1.802(5) . ?
Si1 C17 1.845(7) . ?
Si1 C16 1.960(8) . ?
Si1 N1 1.969(5) . ?
Si1 C1 2.350(7) . ?
Si1 H1 1.50(4) . ?
N2 C1 1.374(8) . ?
N2 C12 1.481(7) . ?
N1 C1 1.302(7) . ?
N1 C8 1.468(8) . ?
C1 C2 1.494(9) . ?
C2 C7 1.366(8) . ?
C2 C3 1.386(9) . ?
C12 C14 1.510(9) . ?
C12 C15 1.520(8) . ?
C12 C13 1.541(8) . ?
C7 C6 1.388(9) . ?
C7 H7 0.9300 . ?
N3 C16 1.147(8) . ?
C3 C4 1.386(9) . ?
C3 H3 0.9300 . ?
C8 C9 1.520(9) . ?
C8 C10 1.515(9) . ?
C8 C11 1.534(9) . ?
C4 C5 1.367(9) . ?
C4 H4 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C6 C5 1.375(10) . ?
C6 H6 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C5 H5 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
N2 Si1 C17 119.6(3) . . ?
N2 Si1 C16 99.3(3) . . ?
C17 Si1 C16 94.8(3) . . ?
N2 Si1 N1 69.3(2) . . ?
C17 Si1 N1 97.0(3) . . ?
C16 Si1 N1 166.6(3) . . ?
N2 Si1 C1 35.7(2) . . ?
C17 Si1 C1 113.1(3) . . ?
C16 Si1 C1 134.3(3) . . ?
N1 Si1 C1 33.7(2) . . ?
N2 Si1 H1 118.4(16) . . ?
C17 Si1 H1 119.8(16) . . ?
C16 Si1 H1 90.8(17) . . ?
N1 Si1 H1 88.8(16) . . ?
C1 Si1 H1 104.2(16) . . ?
C1 N2 C12 129.7(5) . . ?
C1 N2 Si1 94.5(4) . . ?
C12 N2 Si1 134.4(4) . . ?
C1 N1 C8 129.4(6) . . ?
C1 N1 Si1 89.4(4) . . ?
C8 N1 Si1 138.2(4) . . ?
N1 C1 N2 106.7(5) . . ?
N1 C1 C2 127.6(6) . . ?
N2 C1 C2 125.4(6) . . ?
N1 C1 Si1 56.9(3) . . ?
N2 C1 Si1 49.9(3) . . ?
C2 C1 Si1 170.6(5) . . ?
C7 C2 C3 120.7(6) . . ?
C7 C2 C1 118.6(6) . . ?
C3 C2 C1 120.7(6) . . ?
N2 C12 C14 108.0(6) . . ?
N2 C12 C15 108.3(5) . . ?
C14 C12 C15 111.3(6) . . ?
N2 C12 C13 113.5(5) . . ?
C14 C12 C13 109.2(6) . . ?
C15 C12 C13 106.6(6) . . ?
C2 C7 C6 120.4(7) . . ?
C2 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C2 C3 C4 118.4(6) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
N1 C8 C9 105.9(6) . . ?
N1 C8 C10 111.8(6) . . ?
C9 C8 C10 108.3(6) . . ?
N1 C8 C11 111.5(6) . . ?
C9 C8 C11 109.1(6) . . ?
C10 C8 C11 110.1(6) . . ?
C5 C4 C3 121.2(7) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
Si1 C17 H17A 109.5 . . ?
Si1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
Si1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C16 Si1 168.6(7) . . ?
C5 C6 C7 119.3(7) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C5 C6 120.1(7) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.062
_vrf_RINTA01_mo_SEN_109_0m_a     
;
Problem:The value of Rint is greater than 0.25
            Rint given   0.322
RESPONSE:The overall quality of the data is very poor due to the
crystal quality.
;
# end Validation Reply Form


_chemical_properties_physical    ', Air-sensitive,Moisture-sensitive'
