# 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_E-4a
_database_code_depnum_ccdc_archive 'CCDC 1057523'
_audit_update_record             
;
2015-07-02 deposited with the CCDC.
2015-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H30 N2 Si2'
_chemical_formula_sum            'C20 H30 N2 Si2'
_chemical_formula_weight         354.64

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   10.132(5)
_cell_length_b                   13.834(9)
_cell_length_c                   16.460(11)
_cell_angle_alpha                91.96(2)
_cell_angle_beta                 91.53(3)
_cell_angle_gamma                110.682(17)
_cell_volume                     2155(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.093
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9512
_exptl_absorpt_correction_T_max  0.9833
_exptl_absorpt_process_details   
;
Jacobson, R. (1998) Private communication
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       
;
Mercury CCD (2x2 bin mode)
;
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14077
_diffrn_reflns_av_unetI/netI     0.0649
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.084
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.241
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.941
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.941
_reflns_number_total             7330
_reflns_number_gt                5155
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'

_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)+(0.0375P)²+3.1862P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7330
_refine_ls_number_parameters     449
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0769
_refine_ls_wR_factor_ref         0.1651
_refine_ls_wR_factor_gt          0.1468
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_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 0.16758(12) 0.80693(8) 0.14126(6) 0.0343(3) Uani 1 1 d . . . . .
Si2 Si 0.79277(12) 1.16269(9) 0.36224(7) 0.0391(3) Uani 1 1 d . . . . .
Si3 Si 0.20961(11) 0.33134(8) 0.61342(6) 0.0303(3) Uani 1 1 d . . . . .
C11 C 0.5874(4) 1.1150(3) 0.2284(2) 0.0283(8) Uani 1 1 d . . . . .
C1 C 0.3832(4) 0.8546(3) 0.2696(2) 0.0301(8) Uani 1 1 d . . . . .
C2 C 0.2629(4) 0.7803(3) 0.2327(2) 0.0284(8) Uani 1 1 d . . . . .
C12 C 0.7035(4) 1.1904(3) 0.2682(2) 0.0301(8) Uani 1 1 d . . . . .
C3 C 0.2160(4) 0.6832(3) 0.2672(2) 0.0334(9) Uani 1 1 d . . . . .
H1 H 0.1348 0.6307 0.2432 0.040 Uiso 1 1 calc R U . . .
C21 C 0.3981(4) 0.3664(2) 0.48021(19) 0.0244(7) Uani 1 1 d . . . . .
C16 C 0.5236(4) 1.1360(3) 0.1585(2) 0.0344(9) Uani 1 1 d . . . . .
H18 H 0.4452 1.0835 0.1317 0.041 Uiso 1 1 calc R U . . .
C22 C 0.2883(3) 0.2947(3) 0.5199(2) 0.0249(7) Uani 1 1 d . . . . .
C13 C 0.7509(4) 1.2882(3) 0.2356(2) 0.0338(9) Uani 1 1 d . . . . .
H16 H 0.8294 1.3411 0.2618 0.041 Uiso 1 1 calc R U . . .
C6 C 0.4510(4) 0.8337(3) 0.3382(2) 0.0368(9) Uani 1 1 d . . . . .
H3 H 0.5323 0.8857 0.3627 0.044 Uiso 1 1 calc R U . . .
C15 C 0.5753(4) 1.2335(3) 0.1286(2) 0.0328(9) Uani 1 1 d . . . . .
H17 H 0.5325 1.2478 0.0806 0.039 Uiso 1 1 calc R U . . .
C14 C 0.6881(4) 1.3110(3) 0.1669(2) 0.0336(9) Uani 1 1 d . . . . .
C4 C 0.2823(4) 0.6600(3) 0.3348(2) 0.0337(9) Uani 1 1 d . . . . .
C26 C 0.4535(4) 0.3386(3) 0.4105(2) 0.0311(8) Uani 1 1 d . . . . .
H33 H 0.5265 0.3891 0.3838 0.037 Uiso 1 1 calc R U . . .
C23 C 0.2394(4) 0.1932(3) 0.4870(2) 0.0306(8) Uani 1 1 d . . . . .
H31 H 0.1645 0.1428 0.5126 0.037 Uiso 1 1 calc R U . . .
C24 C 0.2951(4) 0.1624(3) 0.4187(2) 0.0320(8) Uani 1 1 d . . . . .
C5 C 0.3994(4) 0.7376(3) 0.3701(2) 0.0390(10) Uani 1 1 d . . . . .
H2 H 0.4449 0.7242 0.4173 0.047 Uiso 1 1 calc R U . . .
C25 C 0.4020(4) 0.2376(3) 0.3805(2) 0.0354(9) Uani 1 1 d . . . . .
H32 H 0.4401 0.2188 0.3329 0.042 Uiso 1 1 calc R U . . .
Si4 Si 0.21479(12) 0.33701(8) 0.11906(7) 0.0371(3) Uani 1 1 d . . . . .
N4 N 0.4469(3) 0.4700(2) 0.01660(17) 0.0308(7) Uani 1 1 d . . . . .
C32 C 0.2903(4) 0.2959(3) 0.0263(2) 0.0289(8) Uani 1 1 d . . . . .
C31 C 0.3987(4) 0.3661(3) -0.0155(2) 0.0296(8) Uani 1 1 d . . . . .
C33 C 0.2442(4) 0.1923(3) -0.0019(2) 0.0337(9) Uani 1 1 d . . . . .
H46 H 0.1727 0.1427 0.0265 0.040 Uiso 1 1 calc R U . . .
C36 C 0.4537(4) 0.3335(3) -0.0840(2) 0.0383(9) Uani 1 1 d . . . . .
H48 H 0.5262 0.3822 -0.1124 0.046 Uiso 1 1 calc R U . . .
C34 C 0.2979(4) 0.1582(3) -0.0697(2) 0.0366(9) Uani 1 1 d . . . . .
C35 C 0.4033(4) 0.2315(3) -0.1102(2) 0.0381(9) Uani 1 1 d . . . . .
H47 H 0.4410 0.2104 -0.1569 0.046 Uiso 1 1 calc R U . . .
C37 C 0.2476(5) 0.0457(3) -0.0962(3) 0.0506(11) Uani 1 1 d . . . . .
H49 H 0.2163 0.0374 -0.1537 0.076 Uiso 1 1 calc R U . . .
H51 H 0.1686 0.0069 -0.0633 0.076 Uiso 1 1 calc R U . . .
H50 H 0.3250 0.0194 -0.0888 0.076 Uiso 1 1 calc R U . . .
N1 N 0.4309(3) 0.9520(2) 0.23180(17) 0.0316(7) Uani 1 1 d . . . . .
N2 N 0.5403(3) 1.0174(2) 0.26526(17) 0.0315(7) Uani 1 1 d . . . . .
N3 N 0.4487(3) 0.4681(2) 0.51697(17) 0.0270(7) Uani 1 1 d . . . . .
C17 C 0.7419(4) 1.4179(3) 0.1335(3) 0.0477(11) Uani 1 1 d . . . . .
H20 H 0.6650 1.4453 0.1306 0.072 Uiso 1 1 calc R U . . .
H19 H 0.7767 1.4140 0.0790 0.072 Uiso 1 1 calc R U . . .
H21 H 0.8189 1.4638 0.1694 0.072 Uiso 1 1 calc R U . . .
C29 C 0.1424(4) 0.4383(3) 0.5957(2) 0.0403(10) Uani 1 1 d . . . . .
H40 H 0.0738 0.4187 0.5495 0.060 Uiso 1 1 calc R U . . .
H41 H 0.2214 0.5010 0.5839 0.060 Uiso 1 1 calc R U . . .
H42 H 0.0967 0.4514 0.6445 0.060 Uiso 1 1 calc R U . . .
C8 C 0.1133(4) 0.9210(3) 0.1586(3) 0.0427(10) Uani 1 1 d . . . . .
H8 H 0.1975 0.9834 0.1680 0.064 Uiso 1 1 calc R U . . .
H7 H 0.0547 0.9109 0.2062 0.064 Uiso 1 1 calc R U . . .
H9 H 0.0591 0.9288 0.1106 0.064 Uiso 1 1 calc R U . . .
C7 C 0.2293(5) 0.5548(3) 0.3692(3) 0.0497(11) Uani 1 1 d . . . . .
H4 H 0.1506 0.5087 0.3344 0.075 Uiso 1 1 calc R U . . .
H6 H 0.1968 0.5600 0.4242 0.075 Uiso 1 1 calc R U . . .
H5 H 0.3056 0.5268 0.3714 0.075 Uiso 1 1 calc R U . . .
C18 C 0.8637(4) 1.0576(3) 0.3420(3) 0.0450(10) Uani 1 1 d . . . . .
H22 H 0.9330 1.0779 0.2995 0.068 Uiso 1 1 calc R U . . .
H23 H 0.7862 0.9941 0.3238 0.068 Uiso 1 1 calc R U . . .
H24 H 0.9093 1.0455 0.3919 0.068 Uiso 1 1 calc R U . . .
C28 C 0.0564(5) 0.2157(3) 0.6384(3) 0.0507(11) Uani 1 1 d . . . . .
H38 H 0.0896 0.1596 0.6524 0.076 Uiso 1 1 calc R U . . .
H37 H -0.0100 0.1933 0.5912 0.076 Uiso 1 1 calc R U . . .
H39 H 0.0089 0.2332 0.6846 0.076 Uiso 1 1 calc R U . . .
C27 C 0.2420(5) 0.0521(3) 0.3856(3) 0.0477(11) Uani 1 1 d . . . . .
H34 H 0.3183 0.0242 0.3893 0.072 Uiso 1 1 calc R U . . .
H35 H 0.2101 0.0495 0.3286 0.072 Uiso 1 1 calc R U . . .
H36 H 0.1630 0.0107 0.4174 0.072 Uiso 1 1 calc R U . . .
C30 C 0.3405(5) 0.3683(3) 0.7005(2) 0.0478(11) Uani 1 1 d . . . . .
H45 H 0.2970 0.3853 0.7488 0.072 Uiso 1 1 calc R U . . .
H44 H 0.4219 0.4286 0.6873 0.072 Uiso 1 1 calc R U . . .
H43 H 0.3718 0.3104 0.7115 0.072 Uiso 1 1 calc R U . . .
C40 C 0.3515(5) 0.3860(4) 0.2019(2) 0.0508(11) Uani 1 1 d . . . . .
H59 H 0.4190 0.4536 0.1884 0.076 Uiso 1 1 calc R U . . .
H58 H 0.4013 0.3373 0.2084 0.076 Uiso 1 1 calc R U . . .
H60 H 0.3070 0.3931 0.2527 0.076 Uiso 1 1 calc R U . . .
C38 C 0.1368(5) 0.4363(4) 0.0965(3) 0.0540(12) Uani 1 1 d . . . . .
H54 H 0.0987 0.4555 0.1462 0.081 Uiso 1 1 calc R U . . .
H52 H 0.0606 0.4084 0.0548 0.081 Uiso 1 1 calc R U . . .
H53 H 0.2097 0.4976 0.0768 0.081 Uiso 1 1 calc R U . . .
C39 C 0.0714(6) 0.2200(4) 0.1530(3) 0.0766(18) Uani 1 1 d . . . . .
H56 H 0.1118 0.1685 0.1694 0.115 Uiso 1 1 calc R U . . .
H55 H 0.0015 0.1906 0.1081 0.115 Uiso 1 1 calc R U . . .
H57 H 0.0256 0.2394 0.1993 0.115 Uiso 1 1 calc R U . . .
C9 C 0.2787(5) 0.8234(4) 0.0511(2) 0.0569(13) Uani 1 1 d . . . . .
H11 H 0.2255 0.8318 0.0030 0.085 Uiso 1 1 calc R U . . .
H12 H 0.3051 0.7623 0.0425 0.085 Uiso 1 1 calc R U . . .
H10 H 0.3642 0.8849 0.0604 0.085 Uiso 1 1 calc R U . . .
C10 C 0.0043(5) 0.6921(3) 0.1211(3) 0.0551(12) Uani 1 1 d . . . . .
H15 H -0.0522 0.6796 0.1697 0.083 Uiso 1 1 calc R U . . .
H14 H 0.0295 0.6315 0.1076 0.083 Uiso 1 1 calc R U . . .
H13 H -0.0508 0.7047 0.0755 0.083 Uiso 1 1 calc R U . . .
C19 C 0.6703(5) 1.1298(4) 0.4477(3) 0.0621(13) Uani 1 1 d . . . . .
H27 H 0.7226 1.1255 0.4976 0.093 Uiso 1 1 calc R U . . .
H25 H 0.5949 1.0631 0.4350 0.093 Uiso 1 1 calc R U . . .
H26 H 0.6291 1.1836 0.4556 0.093 Uiso 1 1 calc R U . . .
C20 C 0.9444(5) 1.2824(3) 0.3929(3) 0.0667(15) Uani 1 1 d . . . . .
H30 H 0.9949 1.2697 0.4406 0.100 Uiso 1 1 calc R U . . .
H29 H 0.9096 1.3384 0.4063 0.100 Uiso 1 1 calc R U . . .
H28 H 1.0087 1.3020 0.3479 0.100 Uiso 1 1 calc R U . . .


_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 C10 1.857(4) . ?
Si1 C9 1.858(4) . ?
Si1 C8 1.862(4) . ?
Si1 C2 1.883(4) . ?
Si2 C18 1.860(4) . ?
Si2 C20 1.861(5) . ?
Si2 C19 1.861(5) . ?
Si2 C12 1.890(4) . ?
Si3 C30 1.856(4) . ?
Si3 C28 1.861(4) . ?
Si3 C29 1.862(4) . ?
Si3 C22 1.886(4) . ?
C11 C16 1.394(5) . ?
C11 C12 1.395(5) . ?
C11 N2 1.428(4) . ?
C1 C2 1.395(5) . ?
C1 C6 1.396(5) . ?
C1 N1 1.432(5) . ?
C2 C3 1.403(5) . ?
C12 C13 1.397(5) . ?
C3 C4 1.389(5) . ?
C3 H1 0.9500 . ?
C21 C26 1.391(5) . ?
C21 C22 1.398(5) . ?
C21 N3 1.423(4) . ?
C16 C15 1.378(5) . ?
C16 H18 0.9500 . ?
C22 C23 1.397(5) . ?
C13 C14 1.383(5) . ?
C13 H16 0.9500 . ?
C6 C5 1.374(5) . ?
C6 H3 0.9500 . ?
C15 C14 1.379(5) . ?
C15 H17 0.9500 . ?
C14 C17 1.513(5) . ?
C4 C5 1.386(5) . ?
C4 C7 1.499(5) . ?
C26 C25 1.376(5) . ?
C26 H33 0.9500 . ?
C23 C24 1.391(5) . ?
C23 H31 0.9500 . ?
C24 C25 1.391(5) . ?
C24 C27 1.504(5) . ?
C5 H2 0.9500 . ?
C25 H32 0.9500 . ?
Si4 C40 1.847(4) . ?
Si4 C38 1.854(4) . ?
Si4 C39 1.867(5) . ?
Si4 C32 1.884(4) . ?
N4 N4 1.256(6) 2_665 ?
N4 C31 1.423(4) . ?
C32 C31 1.399(5) . ?
C32 C33 1.399(5) . ?
C31 C36 1.401(5) . ?
C33 C34 1.393(5) . ?
C33 H46 0.9500 . ?
C36 C35 1.369(5) . ?
C36 H48 0.9500 . ?
C34 C35 1.390(5) . ?
C34 C37 1.501(5) . ?
C35 H47 0.9500 . ?
C37 H49 0.9800 . ?
C37 H51 0.9800 . ?
C37 H50 0.9800 . ?
N1 N2 1.255(4) . ?
N3 N3 1.260(5) 2_666 ?
C17 H20 0.9800 . ?
C17 H19 0.9800 . ?
C17 H21 0.9800 . ?
C29 H40 0.9800 . ?
C29 H41 0.9800 . ?
C29 H42 0.9800 . ?
C8 H8 0.9800 . ?
C8 H7 0.9800 . ?
C8 H9 0.9800 . ?
C7 H4 0.9800 . ?
C7 H6 0.9800 . ?
C7 H5 0.9800 . ?
C18 H22 0.9800 . ?
C18 H23 0.9800 . ?
C18 H24 0.9800 . ?
C28 H38 0.9800 . ?
C28 H37 0.9800 . ?
C28 H39 0.9800 . ?
C27 H34 0.9800 . ?
C27 H35 0.9800 . ?
C27 H36 0.9800 . ?
C30 H45 0.9800 . ?
C30 H44 0.9800 . ?
C30 H43 0.9800 . ?
C40 H59 0.9800 . ?
C40 H58 0.9800 . ?
C40 H60 0.9800 . ?
C38 H54 0.9800 . ?
C38 H52 0.9800 . ?
C38 H53 0.9800 . ?
C39 H56 0.9800 . ?
C39 H55 0.9800 . ?
C39 H57 0.9800 . ?
C9 H11 0.9800 . ?
C9 H12 0.9800 . ?
C9 H10 0.9800 . ?
C10 H15 0.9800 . ?
C10 H14 0.9800 . ?
C10 H13 0.9800 . ?
C19 H27 0.9800 . ?
C19 H25 0.9800 . ?
C19 H26 0.9800 . ?
C20 H30 0.9800 . ?
C20 H29 0.9800 . ?
C20 H28 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
C10 Si1 C9 108.6(2) . . ?
C10 Si1 C8 107.4(2) . . ?
C9 Si1 C8 110.6(2) . . ?
C10 Si1 C2 107.18(18) . . ?
C9 Si1 C2 110.03(19) . . ?
C8 Si1 C2 112.77(17) . . ?
C18 Si2 C20 107.7(2) . . ?
C18 Si2 C19 110.2(2) . . ?
C20 Si2 C19 108.3(2) . . ?
C18 Si2 C12 111.77(18) . . ?
C20 Si2 C12 107.54(19) . . ?
C19 Si2 C12 111.1(2) . . ?
C30 Si3 C28 109.3(2) . . ?
C30 Si3 C29 109.7(2) . . ?
C28 Si3 C29 107.5(2) . . ?
C30 Si3 C22 110.71(18) . . ?
C28 Si3 C22 107.15(18) . . ?
C29 Si3 C22 112.30(17) . . ?
C16 C11 C12 121.4(3) . . ?
C16 C11 N2 123.7(3) . . ?
C12 C11 N2 114.9(3) . . ?
C2 C1 C6 121.6(3) . . ?
C2 C1 N1 115.1(3) . . ?
C6 C1 N1 123.3(3) . . ?
C1 C2 C3 116.2(3) . . ?
C1 C2 Si1 122.5(3) . . ?
C3 C2 Si1 121.2(3) . . ?
C11 C12 C13 116.9(3) . . ?
C11 C12 Si2 121.9(3) . . ?
C13 C12 Si2 121.1(3) . . ?
C4 C3 C2 123.4(4) . . ?
C4 C3 H1 118.3 . . ?
C2 C3 H1 118.3 . . ?
C26 C21 C22 121.7(3) . . ?
C26 C21 N3 123.3(3) . . ?
C22 C21 N3 115.0(3) . . ?
C15 C16 C11 119.2(3) . . ?
C15 C16 H18 120.4 . . ?
C11 C16 H18 120.4 . . ?
C23 C22 C21 116.5(3) . . ?
C23 C22 Si3 121.2(3) . . ?
C21 C22 Si3 122.3(3) . . ?
C14 C13 C12 122.6(4) . . ?
C14 C13 H16 118.7 . . ?
C12 C13 H16 118.7 . . ?
C5 C6 C1 119.7(4) . . ?
C5 C6 H3 120.2 . . ?
C1 C6 H3 120.2 . . ?
C16 C15 C14 121.3(4) . . ?
C16 C15 H17 119.3 . . ?
C14 C15 H17 119.3 . . ?
C15 C14 C13 118.4(3) . . ?
C15 C14 C17 120.3(4) . . ?
C13 C14 C17 121.2(4) . . ?
C5 C4 C3 117.8(3) . . ?
C5 C4 C7 120.7(4) . . ?
C3 C4 C7 121.5(4) . . ?
C25 C26 C21 119.7(3) . . ?
C25 C26 H33 120.2 . . ?
C21 C26 H33 120.2 . . ?
C24 C23 C22 123.2(3) . . ?
C24 C23 H31 118.4 . . ?
C22 C23 H31 118.4 . . ?
C23 C24 C25 117.8(3) . . ?
C23 C24 C27 122.0(3) . . ?
C25 C24 C27 120.2(3) . . ?
C6 C5 C4 121.3(4) . . ?
C6 C5 H2 119.3 . . ?
C4 C5 H2 119.3 . . ?
C26 C25 C24 121.1(3) . . ?
C26 C25 H32 119.4 . . ?
C24 C25 H32 119.4 . . ?
C40 Si4 C38 109.9(2) . . ?
C40 Si4 C39 108.9(2) . . ?
C38 Si4 C39 108.2(2) . . ?
C40 Si4 C32 110.54(19) . . ?
C38 Si4 C32 112.04(19) . . ?
C39 Si4 C32 107.21(19) . . ?
N4 N4 C31 114.6(4) 2_665 . ?
C31 C32 C33 116.8(3) . . ?
C31 C32 Si4 121.9(3) . . ?
C33 C32 Si4 121.3(3) . . ?
C32 C31 C36 120.8(3) . . ?
C32 C31 N4 115.4(3) . . ?
C36 C31 N4 123.8(3) . . ?
C34 C33 C32 123.2(3) . . ?
C34 C33 H46 118.4 . . ?
C32 C33 H46 118.4 . . ?
C35 C36 C31 120.2(4) . . ?
C35 C36 H48 119.9 . . ?
C31 C36 H48 119.9 . . ?
C35 C34 C33 117.7(3) . . ?
C35 C34 C37 121.1(4) . . ?
C33 C34 C37 121.1(4) . . ?
C36 C35 C34 121.2(4) . . ?
C36 C35 H47 119.4 . . ?
C34 C35 H47 119.4 . . ?
C34 C37 H49 109.5 . . ?
C34 C37 H51 109.5 . . ?
H49 C37 H51 109.5 . . ?
C34 C37 H50 109.5 . . ?
H49 C37 H50 109.5 . . ?
H51 C37 H50 109.5 . . ?
N2 N1 C1 114.1(3) . . ?
N1 N2 C11 114.4(3) . . ?
N3 N3 C21 115.0(4) 2_666 . ?
C14 C17 H20 109.5 . . ?
C14 C17 H19 109.5 . . ?
H20 C17 H19 109.5 . . ?
C14 C17 H21 109.5 . . ?
H20 C17 H21 109.5 . . ?
H19 C17 H21 109.5 . . ?
Si3 C29 H40 109.5 . . ?
Si3 C29 H41 109.5 . . ?
H40 C29 H41 109.5 . . ?
Si3 C29 H42 109.5 . . ?
H40 C29 H42 109.5 . . ?
H41 C29 H42 109.5 . . ?
Si1 C8 H8 109.5 . . ?
Si1 C8 H7 109.5 . . ?
H8 C8 H7 109.5 . . ?
Si1 C8 H9 109.5 . . ?
H8 C8 H9 109.5 . . ?
H7 C8 H9 109.5 . . ?
C4 C7 H4 109.5 . . ?
C4 C7 H6 109.5 . . ?
H4 C7 H6 109.5 . . ?
C4 C7 H5 109.5 . . ?
H4 C7 H5 109.5 . . ?
H6 C7 H5 109.5 . . ?
Si2 C18 H22 109.5 . . ?
Si2 C18 H23 109.5 . . ?
H22 C18 H23 109.5 . . ?
Si2 C18 H24 109.5 . . ?
H22 C18 H24 109.5 . . ?
H23 C18 H24 109.5 . . ?
Si3 C28 H38 109.5 . . ?
Si3 C28 H37 109.5 . . ?
H38 C28 H37 109.5 . . ?
Si3 C28 H39 109.5 . . ?
H38 C28 H39 109.5 . . ?
H37 C28 H39 109.5 . . ?
C24 C27 H34 109.5 . . ?
C24 C27 H35 109.5 . . ?
H34 C27 H35 109.5 . . ?
C24 C27 H36 109.5 . . ?
H34 C27 H36 109.5 . . ?
H35 C27 H36 109.5 . . ?
Si3 C30 H45 109.5 . . ?
Si3 C30 H44 109.5 . . ?
H45 C30 H44 109.5 . . ?
Si3 C30 H43 109.5 . . ?
H45 C30 H43 109.5 . . ?
H44 C30 H43 109.5 . . ?
Si4 C40 H59 109.5 . . ?
Si4 C40 H58 109.5 . . ?
H59 C40 H58 109.5 . . ?
Si4 C40 H60 109.5 . . ?
H59 C40 H60 109.5 . . ?
H58 C40 H60 109.5 . . ?
Si4 C38 H54 109.5 . . ?
Si4 C38 H52 109.5 . . ?
H54 C38 H52 109.5 . . ?
Si4 C38 H53 109.5 . . ?
H54 C38 H53 109.5 . . ?
H52 C38 H53 109.5 . . ?
Si4 C39 H56 109.5 . . ?
Si4 C39 H55 109.5 . . ?
H56 C39 H55 109.5 . . ?
Si4 C39 H57 109.5 . . ?
H56 C39 H57 109.5 . . ?
H55 C39 H57 109.5 . . ?
Si1 C9 H11 109.5 . . ?
Si1 C9 H12 109.5 . . ?
H11 C9 H12 109.5 . . ?
Si1 C9 H10 109.5 . . ?
H11 C9 H10 109.5 . . ?
H12 C9 H10 109.5 . . ?
Si1 C10 H15 109.5 . . ?
Si1 C10 H14 109.5 . . ?
H15 C10 H14 109.5 . . ?
Si1 C10 H13 109.5 . . ?
H15 C10 H13 109.5 . . ?
H14 C10 H13 109.5 . . ?
Si2 C19 H27 109.5 . . ?
Si2 C19 H25 109.5 . . ?
H27 C19 H25 109.5 . . ?
Si2 C19 H26 109.5 . . ?
H27 C19 H26 109.5 . . ?
H25 C19 H26 109.5 . . ?
Si2 C20 H30 109.5 . . ?
Si2 C20 H29 109.5 . . ?
H30 C20 H29 109.5 . . ?
Si2 C20 H28 109.5 . . ?
H30 C20 H28 109.5 . . ?
H29 C20 H28 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
C6 C1 C2 C3 -1.3(5) . . . . ?
N1 C1 C2 C3 178.4(3) . . . . ?
C6 C1 C2 Si1 178.9(3) . . . . ?
N1 C1 C2 Si1 -1.3(4) . . . . ?
C10 Si1 C2 C1 -173.6(3) . . . . ?
C9 Si1 C2 C1 68.5(3) . . . . ?
C8 Si1 C2 C1 -55.5(3) . . . . ?
C10 Si1 C2 C3 6.7(4) . . . . ?
C9 Si1 C2 C3 -111.2(3) . . . . ?
C8 Si1 C2 C3 124.7(3) . . . . ?
C16 C11 C12 C13 1.2(5) . . . . ?
N2 C11 C12 C13 -178.2(3) . . . . ?
C16 C11 C12 Si2 -179.1(3) . . . . ?
N2 C11 C12 Si2 1.4(4) . . . . ?
C18 Si2 C12 C11 60.2(4) . . . . ?
C20 Si2 C12 C11 178.2(3) . . . . ?
C19 Si2 C12 C11 -63.4(4) . . . . ?
C18 Si2 C12 C13 -120.2(3) . . . . ?
C20 Si2 C12 C13 -2.1(4) . . . . ?
C19 Si2 C12 C13 116.3(3) . . . . ?
C1 C2 C3 C4 0.6(5) . . . . ?
Si1 C2 C3 C4 -179.7(3) . . . . ?
C12 C11 C16 C15 -0.7(6) . . . . ?
N2 C11 C16 C15 178.6(3) . . . . ?
C26 C21 C22 C23 1.4(5) . . . . ?
N3 C21 C22 C23 -177.9(3) . . . . ?
C26 C21 C22 Si3 -178.9(3) . . . . ?
N3 C21 C22 Si3 1.8(4) . . . . ?
C30 Si3 C22 C23 113.1(3) . . . . ?
C28 Si3 C22 C23 -6.1(3) . . . . ?
C29 Si3 C22 C23 -123.9(3) . . . . ?
C30 Si3 C22 C21 -66.6(3) . . . . ?
C28 Si3 C22 C21 174.3(3) . . . . ?
C29 Si3 C22 C21 56.4(3) . . . . ?
C11 C12 C13 C14 -0.4(5) . . . . ?
Si2 C12 C13 C14 180.0(3) . . . . ?
C2 C1 C6 C5 0.6(6) . . . . ?
N1 C1 C6 C5 -179.2(3) . . . . ?
C11 C16 C15 C14 -0.6(6) . . . . ?
C16 C15 C14 C13 1.4(6) . . . . ?
C16 C15 C14 C17 -179.3(4) . . . . ?
C12 C13 C14 C15 -0.9(6) . . . . ?
C12 C13 C14 C17 179.8(4) . . . . ?
C2 C3 C4 C5 0.9(6) . . . . ?
C2 C3 C4 C7 -179.4(4) . . . . ?
C22 C21 C26 C25 -1.6(5) . . . . ?
N3 C21 C26 C25 177.6(3) . . . . ?
C21 C22 C23 C24 0.3(5) . . . . ?
Si3 C22 C23 C24 -179.4(3) . . . . ?
C22 C23 C24 C25 -1.8(5) . . . . ?
C22 C23 C24 C27 178.8(4) . . . . ?
C1 C6 C5 C4 1.1(6) . . . . ?
C3 C4 C5 C6 -1.8(6) . . . . ?
C7 C4 C5 C6 178.5(4) . . . . ?
C21 C26 C25 C24 0.0(6) . . . . ?
C23 C24 C25 C26 1.6(5) . . . . ?
C27 C24 C25 C26 -179.0(4) . . . . ?
C40 Si4 C32 C31 -62.8(3) . . . . ?
C38 Si4 C32 C31 60.2(4) . . . . ?
C39 Si4 C32 C31 178.7(3) . . . . ?
C40 Si4 C32 C33 114.5(3) . . . . ?
C38 Si4 C32 C33 -122.6(3) . . . . ?
C39 Si4 C32 C33 -4.0(4) . . . . ?
C33 C32 C31 C36 2.2(5) . . . . ?
Si4 C32 C31 C36 179.6(3) . . . . ?
C33 C32 C31 N4 -177.7(3) . . . . ?
Si4 C32 C31 N4 -0.3(4) . . . . ?
N4 N4 C31 C32 173.3(4) 2_665 . . . ?
N4 N4 C31 C36 -6.5(6) 2_665 . . . ?
C31 C32 C33 C34 -1.9(5) . . . . ?
Si4 C32 C33 C34 -179.3(3) . . . . ?
C32 C31 C36 C35 -1.1(6) . . . . ?
N4 C31 C36 C35 178.8(3) . . . . ?
C32 C33 C34 C35 0.5(6) . . . . ?
C32 C33 C34 C37 178.3(4) . . . . ?
C31 C36 C35 C34 -0.4(6) . . . . ?
C33 C34 C35 C36 0.7(6) . . . . ?
C37 C34 C35 C36 -177.1(4) . . . . ?
C2 C1 N1 N2 -179.1(3) . . . . ?
C6 C1 N1 N2 0.6(5) . . . . ?
C1 N1 N2 C11 -179.3(3) . . . . ?
C16 C11 N2 N1 -3.4(5) . . . . ?
C12 C11 N2 N1 176.0(3) . . . . ?
C26 C21 N3 N3 -1.9(5) . . . 2_666 ?
C22 C21 N3 N3 177.4(4) . . . 2_666 ?

_refine_diff_density_max         0.288
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_E-4d
_database_code_depnum_ccdc_archive 'CCDC 1057524'
_audit_update_record             
;
2015-07-02 deposited with the CCDC.
2015-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H24 F2 N2 Si2'
_chemical_formula_sum            'C18 H24 F2 N2 Si2'
_chemical_formula_weight         362.57

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'
F F 0.0171 0.0103 '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           64
_space_group_name_H-M_alt        'C m c a'
_space_group_name_Hall           '-C 2bc 2'

_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, -y+1/2, z+1/2'
'x, -y, -z'
'-x+1/2, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x, y, z'
'x-1/2, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z-1/2'

_cell_length_a                   7.290(5)
_cell_length_b                   16.889(12)
_cell_length_c                   15.688(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1932(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2632
_cell_measurement_theta_min      3.0434
_cell_measurement_theta_max      27.3871

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.204
_shelx_estimated_absorpt_T_min   0.905
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8225
_exptl_absorpt_process_details   
;
Jacobson, R. (1998) Private communication
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       
;
Mercury CCD (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 14.5666
_diffrn_measurement_method       dtprofit.ref
_diffrn_reflns_number            7144
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.309
_diffrn_reflns_theta_max         27.391
_diffrn_reflns_theta_full        25.241
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1176
_reflns_number_gt                973
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_measurement_details      
;
scan:
	Number of images: 600
	           Slice: -70.0000 - 110.0000
	     Image width: 0.3000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.3361
	          2theta: 19.6775
scan:
	Number of images: 600
	           Slice: -70.0000 - 110.0000
	     Image width: 0.3000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.3361
	          2theta: 19.6775

;
_diffrn_measurement_device_details 
;
AFC8: Eulerian 3-circle
;
_diffrn_orient_matrix_UB_11      0.0115
_diffrn_orient_matrix_UB_12      -0.0041
_diffrn_orient_matrix_UB_13      -0.1366
_diffrn_orient_matrix_UB_21      0.0267
_diffrn_orient_matrix_UB_22      0.0528
_diffrn_orient_matrix_UB_23      0.0007
_diffrn_orient_matrix_UB_31      0.0566
_diffrn_orient_matrix_UB_32      -0.0287
_diffrn_orient_matrix_UB_33      0.0056
_diffrn_orient_matrix_type       d*Trek

_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       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'

_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)+(0.0590P)²+1.7300P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1176
_refine_ls_number_parameters     72
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1286
_refine_ls_wR_factor_gt          0.1207
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_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_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 0.0000 0.11864(4) 0.12996(5) 0.0251(3) Uani 1 2 d S T P . .
F1 F 0.0000 0.15839(9) 0.22498(10) 0.0415(5) Uani 1 2 d S T P . .
N1 N 0.0000 -0.03671(12) 0.00924(13) 0.0220(5) Uani 1 2 d S T P . .
C6 C 0.0000 -0.13121(16) 0.12357(17) 0.0276(6) Uani 1 2 d S T P . .
H3 H 0.0000 -0.1720 0.0818 0.033 Uiso 1 2 calc R U P . .
C1 C 0.0000 -0.05166(14) 0.09825(17) 0.0227(5) Uani 1 2 d S T P . .
C2 C 0.0000 0.01051(14) 0.15892(17) 0.0223(5) Uani 1 2 d S T P . .
C4 C 0.0000 -0.09140(17) 0.27142(17) 0.0276(6) Uani 1 2 d S T P . .
C3 C 0.0000 -0.01208(15) 0.24496(18) 0.0260(6) Uani 1 2 d S T P . .
H1 H 0.0000 0.0282 0.2872 0.031 Uiso 1 2 calc R U P . .
C7 C 0.0000 -0.11138(19) 0.36531(18) 0.0353(7) Uani 1 2 d S T P . .
H4 H -0.0674 -0.1609 0.3745 0.053 Uiso 0.5 1 calc R U P . .
H5 H -0.0592 -0.0686 0.3972 0.053 Uiso 0.5 1 calc R U P . .
H6 H 0.1267 -0.1177 0.3851 0.053 Uiso 0.5 1 calc R U P . .
C8 C 0.2204(3) 0.15780(12) 0.08694(14) 0.0373(5) Uani 1 1 d . . . . .
H7 H 0.2665 0.1220 0.0427 0.056 Uiso 1 1 calc R U . . .
H8 H 0.3106 0.1615 0.1331 0.056 Uiso 1 1 calc R U . . .
H9 H 0.2001 0.2105 0.0625 0.056 Uiso 1 1 calc R U . . .
C5 C 0.0000 -0.15054(16) 0.20947(18) 0.0304(6) Uani 1 2 d S T P . .
H2 H 0.0000 -0.2046 0.2262 0.036 Uiso 1 2 calc R U P . .


_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 F1 1.635(2) . ?
Si1 C8 1.864(2) 11 ?
Si1 C8 1.864(2) . ?
Si1 C2 1.882(3) . ?
N1 N1 1.274(4) 9 ?
N1 C1 1.419(4) . ?
C6 C5 1.387(4) . ?
C6 C1 1.401(4) . ?
C6 H3 0.9500 . ?
C1 C2 1.417(4) . ?
C2 C3 1.403(4) . ?
C4 C5 1.394(4) . ?
C4 C3 1.402(4) . ?
C4 C7 1.511(4) . ?
C3 H1 0.9500 . ?
C7 H4 0.9800 . ?
C7 H5 0.9800 . ?
C7 H6 0.9800 . ?
C8 H7 0.9800 . ?
C8 H8 0.9800 . ?
C8 H9 0.9800 . ?
C5 H2 0.9500 . ?

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
F1 Si1 C8 100.63(8) . 11 ?
F1 Si1 C8 100.63(8) . . ?
C8 Si1 C8 119.09(14) 11 . ?
F1 Si1 C2 100.27(11) . . ?
C8 Si1 C2 115.57(8) 11 . ?
C8 Si1 C2 115.58(8) . . ?
N1 N1 C1 113.4(3) 9 . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 H3 120.0 . . ?
C1 C6 H3 120.0 . . ?
C6 C1 C2 121.3(3) . . ?
C6 C1 N1 116.7(2) . . ?
C2 C1 N1 121.9(2) . . ?
C3 C2 C1 116.4(2) . . ?
C3 C2 Si1 119.76(19) . . ?
C1 C2 Si1 123.8(2) . . ?
C5 C4 C3 118.6(2) . . ?
C5 C4 C7 121.3(3) . . ?
C3 C4 C7 120.1(3) . . ?
C4 C3 C2 123.0(2) . . ?
C4 C3 H1 118.5 . . ?
C2 C3 H1 118.5 . . ?
C4 C7 H4 109.5 . . ?
C4 C7 H5 109.5 . . ?
H4 C7 H5 109.5 . . ?
C4 C7 H6 109.5 . . ?
H4 C7 H6 109.5 . . ?
H5 C7 H6 109.5 . . ?
Si1 C8 H7 109.5 . . ?
Si1 C8 H8 109.5 . . ?
H7 C8 H8 109.5 . . ?
Si1 C8 H9 109.5 . . ?
H7 C8 H9 109.5 . . ?
H8 C8 H9 109.5 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H2 119.7 . . ?
C4 C5 H2 119.7 . . ?

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
C5 C6 C1 C2 0.000(0) . . . . ?
C5 C6 C1 N1 180.0 . . . . ?
N1 N1 C1 C6 180.0 9 . . . ?
N1 N1 C1 C2 0.000(0) 9 . . . ?
C6 C1 C2 C3 0.000(0) . . . . ?
N1 C1 C2 C3 180.000(0) . . . . ?
C6 C1 C2 Si1 180.0 . . . . ?
N1 C1 C2 Si1 0.0 . . . . ?
F1 Si1 C2 C3 0.000(0) . . . . ?
C8 Si1 C2 C3 -107.13(9) 11 . . . ?
C8 Si1 C2 C3 107.13(9) . . . . ?
F1 Si1 C2 C1 180.000(0) . . . . ?
C8 Si1 C2 C1 72.87(9) 11 . . . ?
C8 Si1 C2 C1 -72.87(9) . . . . ?
C5 C4 C3 C2 0.000(0) . . . . ?
C7 C4 C3 C2 180.000(0) . . . . ?
C1 C2 C3 C4 0.000(0) . . . . ?
Si1 C2 C3 C4 180.000(0) . . . . ?
C1 C6 C5 C4 0.000(0) . . . . ?
C3 C4 C5 C6 0.000(0) . . . . ?
C7 C4 C5 C6 180.000(0) . . . . ?

_refine_diff_density_max         0.286
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.061

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_E-4e
_database_code_depnum_ccdc_archive 'CCDC 1057525'
_audit_update_record             
;
2015-07-02 deposited with the CCDC.
2015-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 F6 N2 Si2'
_chemical_formula_sum            'C14 H12 F6 N2 Si2'
_chemical_formula_weight         378.44

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'
F F 0.0171 0.0103 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.992(5)
_cell_length_b                   12.925(8)
_cell_length_c                   7.595(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.626(7)
_cell_angle_gamma                90
_cell_volume                     783.7(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1832
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      26.96

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.6015
_exptl_absorpt_correction_T_max  0.7455
_shelx_estimated_absorpt_T_min   0.9443
_shelx_estimated_absorpt_T_max   0.9942

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4029
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.551
_diffrn_reflns_theta_max         27.230
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             1684
_reflns_number_gt                1316
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'

_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)+(0.0500P)²+3.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1684
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0711
_refine_ls_wR_factor_ref         0.1721
_refine_ls_wR_factor_gt          0.1633
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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 0.21505(14) 0.34712(10) 0.07576(15) 0.0302(3) Uani 1 1 d . . . . .
F1 F 0.3014(3) 0.2376(2) 0.1059(4) 0.0460(7) Uani 1 1 d . . . . .
F2 F 0.2470(3) 0.3956(2) 0.2645(3) 0.0425(7) Uani 1 1 d . . . . .
F3 F 0.3342(3) 0.3977(2) -0.0584(3) 0.0361(6) Uani 1 1 d . . . . .
N1 N -0.0737(4) 0.4932(3) -0.0297(4) 0.0245(7) Uani 1 1 d . . . . .
C1 C -0.1179(5) 0.3877(3) -0.0473(5) 0.0240(8) Uani 1 1 d . . . . .
C2 C 0.0001(5) 0.3109(3) -0.0015(5) 0.0251(8) Uani 1 1 d . . . . .
C3 C -0.0503(5) 0.2091(3) -0.0191(5) 0.0279(8) Uani 1 1 d . . . . .
H1 H 0.0275 0.1557 0.0114 0.033 Uiso 1 1 calc R U . . .
C4 C -0.2129(5) 0.1819(3) -0.0807(5) 0.0284(8) Uani 1 1 d . . . . .
C5 C -0.3256(5) 0.2606(3) -0.1251(5) 0.0293(9) Uani 1 1 d . . . . .
H2 H -0.4358 0.2435 -0.1674 0.035 Uiso 1 1 calc R U . . .
C6 C -0.2798(5) 0.3632(3) -0.1088(5) 0.0279(8) Uani 1 1 d . . . . .
H3 H -0.3579 0.4165 -0.1391 0.034 Uiso 1 1 calc R U . . .
C7 C -0.2659(7) 0.0705(4) -0.0977(6) 0.0406(11) Uani 1 1 d . . . . .
H4 H -0.1718 0.0255 -0.0612 0.061 Uiso 1 1 calc R U . . .
H5 H -0.3601 0.0575 -0.0224 0.061 Uiso 1 1 calc R U . . .
H6 H -0.3004 0.0557 -0.2207 0.061 Uiso 1 1 calc R U . . .


_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 F3 1.569(3) . ?
Si1 F2 1.575(3) . ?
Si1 F1 1.587(3) . ?
Si1 C2 1.850(4) . ?
N1 N1 1.255(6) 3_565 ?
N1 C1 1.413(5) . ?
C1 C6 1.392(5) . ?
C1 C2 1.402(5) . ?
C2 C3 1.381(6) . ?
C3 C4 1.405(6) . ?
C3 H1 0.9500 . ?
C4 C5 1.390(6) . ?
C4 C7 1.506(6) . ?
C5 C6 1.379(6) . ?
C5 H2 0.9500 . ?
C6 H3 0.9500 . ?
C7 H4 0.9800 . ?
C7 H5 0.9800 . ?
C7 H6 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
F3 Si1 F2 110.32(16) . . ?
F3 Si1 F1 101.11(16) . . ?
F2 Si1 F1 99.93(16) . . ?
F3 Si1 C2 118.81(16) . . ?
F2 Si1 C2 119.95(17) . . ?
F1 Si1 C2 102.18(17) . . ?
N1 N1 C1 113.3(4) 3_565 . ?
C6 C1 C2 121.7(4) . . ?
C6 C1 N1 118.4(3) . . ?
C2 C1 N1 119.9(3) . . ?
C3 C2 C1 117.5(4) . . ?
C3 C2 Si1 122.3(3) . . ?
C1 C2 Si1 120.2(3) . . ?
C2 C3 C4 122.1(4) . . ?
C2 C3 H1 118.9 . . ?
C4 C3 H1 118.9 . . ?
C5 C4 C3 118.5(4) . . ?
C5 C4 C7 120.2(4) . . ?
C3 C4 C7 121.3(4) . . ?
C6 C5 C4 121.0(4) . . ?
C6 C5 H2 119.5 . . ?
C4 C5 H2 119.5 . . ?
C5 C6 C1 119.2(4) . . ?
C5 C6 H3 120.4 . . ?
C1 C6 H3 120.4 . . ?
C4 C7 H4 109.5 . . ?
C4 C7 H5 109.5 . . ?
H4 C7 H5 109.5 . . ?
C4 C7 H6 109.5 . . ?
H4 C7 H6 109.5 . . ?
H5 C7 H6 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 N1 C1 C6 178.7(4) 3_565 . . . ?
N1 N1 C1 C2 -0.6(5) 3_565 . . . ?
C6 C1 C2 C3 -0.1(5) . . . . ?
N1 C1 C2 C3 179.2(3) . . . . ?
C6 C1 C2 Si1 178.9(3) . . . . ?
N1 C1 C2 Si1 -1.8(5) . . . . ?
F3 Si1 C2 C3 110.5(3) . . . . ?
F2 Si1 C2 C3 -108.7(3) . . . . ?
F1 Si1 C2 C3 0.4(4) . . . . ?
F3 Si1 C2 C1 -68.5(3) . . . . ?
F2 Si1 C2 C1 72.3(3) . . . . ?
F1 Si1 C2 C1 -178.6(3) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
Si1 C2 C3 C4 -178.9(3) . . . . ?
C2 C3 C4 C5 0.1(6) . . . . ?
C2 C3 C4 C7 -179.5(4) . . . . ?
C3 C4 C5 C6 -0.3(6) . . . . ?
C7 C4 C5 C6 179.4(4) . . . . ?
C4 C5 C6 C1 0.2(6) . . . . ?
C2 C1 C6 C5 0.0(6) . . . . ?
N1 C1 C6 C5 -179.3(3) . . . . ?

_refine_diff_density_max         1.059
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.107

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_Z-4d
_database_code_depnum_ccdc_archive 'CCDC 1057526'
_audit_update_record             
;
2015-07-02 deposited with the CCDC.
2015-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H24 F2 N2 Si2'
_chemical_formula_sum            'C18 H24 F2 N2 Si2'
_chemical_formula_weight         362.57

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'
F F 0.0171 0.0103 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   8.9666(5)
_cell_length_b                   10.7053(7)
_cell_length_c                   11.2276(7)
_cell_angle_alpha                93.383(2)
_cell_angle_beta                 106.763(2)
_cell_angle_gamma                99.798(2)
_cell_volume                     1010.19(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9709
_cell_measurement_theta_min      2.4191
_cell_measurement_theta_max      29.6287

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.195
_shelx_estimated_absorpt_T_min   0.890
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.6062
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            35781
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.907
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             3575
_reflns_number_gt                3359
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_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)+(0.0400P)²+0.6000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3575
_refine_ls_number_parameters     224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0880
_refine_ls_wR_factor_gt          0.0846
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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_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
N1 N 0.19854(14) 0.73879(11) 0.70839(11) 0.0248(3) Uani 1 1 d . . . . .
N2 N 0.21916(14) 0.76524(12) 0.60608(11) 0.0248(3) Uani 1 1 d . . . . .
F1 F 0.17264(13) 0.89161(11) 1.08218(9) 0.0471(3) Uani 1 1 d . . . . .
F2 F 0.34926(12) 0.54938(10) 0.29843(10) 0.0448(3) Uani 1 1 d . . . . .
Si1 Si 0.14046(5) 0.85121(4) 0.93514(4) 0.02748(13) Uani 1 1 d . . . . .
Si2 Si 0.25639(5) 0.60200(4) 0.38773(4) 0.02540(13) Uani 1 1 d . . . . .
C1 C 0.32556(17) 0.72551(13) 0.81704(13) 0.0228(3) Uani 1 1 d . . . . .
C2 C 0.30732(17) 0.76870(13) 0.93144(14) 0.0241(3) Uani 1 1 d . . . . .
C3 C 0.42058(18) 0.75103(15) 1.04098(14) 0.0289(3) Uani 1 1 d . . . . .
H1 H 0.4137 0.7835 1.1194 0.035 Uiso 1 1 calc R U . . .
C4 C 0.54303(18) 0.68746(15) 1.03910(15) 0.0295(3) Uani 1 1 d . . . . .
C5 C 0.55264(18) 0.64103(14) 0.92385(15) 0.0288(3) Uani 1 1 d . . . . .
H2 H 0.6337 0.5952 0.9212 0.035 Uiso 1 1 calc R U . . .
C6 C 0.44634(17) 0.66032(14) 0.81274(14) 0.0261(3) Uani 1 1 d . . . . .
H3 H 0.4556 0.6295 0.7346 0.031 Uiso 1 1 calc R U . . .
C7 C 0.6617(2) 0.66790(18) 1.15935(17) 0.0413(4) Uani 1 1 d . . . . .
H7 H 0.7307 0.6129 1.1405 0.062 Uiso 1 1 calc R U . . .
H8 H 0.6051 0.6275 1.2142 0.062 Uiso 1 1 calc R U . . .
H9 H 0.7262 0.7506 1.2014 0.062 Uiso 1 1 calc R U . . .
C8 C 0.37555(16) 0.80237(13) 0.59200(13) 0.0221(3) Uani 1 1 d . . . . .
C9 C 0.40356(16) 0.73959(13) 0.49001(13) 0.0214(3) Uani 1 1 d . . . . .
C10 C 0.55037(17) 0.78074(14) 0.47037(14) 0.0244(3) Uani 1 1 d . . . . .
H4 H 0.5738 0.7380 0.4034 0.029 Uiso 1 1 calc R U . . .
C11 C 0.66367(17) 0.88228(14) 0.54562(14) 0.0269(3) Uani 1 1 d . . . . .
C12 C 0.62810(18) 0.94390(14) 0.64307(14) 0.0291(3) Uani 1 1 d . . . . .
H5 H 0.7030 1.0143 0.6941 0.035 Uiso 1 1 calc R U . . .
C13 C 0.48533(18) 0.90467(14) 0.66737(14) 0.0269(3) Uani 1 1 d . . . . .
H6 H 0.4628 0.9473 0.7349 0.032 Uiso 1 1 calc R U . . .
C14 C 0.82024(19) 0.92316(18) 0.52004(17) 0.0387(4) Uani 1 1 d . . . . .
H10 H 0.8650 1.0124 0.5546 0.058 Uiso 1 1 calc R U . . .
H11 H 0.8032 0.9144 0.4295 0.058 Uiso 1 1 calc R U . . .
H12 H 0.8941 0.8692 0.5594 0.058 Uiso 1 1 calc R U . . .
C15 C -0.0576(2) 0.74735(19) 0.8789(2) 0.0455(5) Uani 1 1 d . . . . .
H13 H -0.1368 0.7942 0.8934 0.068 Uiso 1 1 calc R U . . .
H14 H -0.0580 0.6719 0.9243 0.068 Uiso 1 1 calc R U . . .
H15 H -0.0835 0.7207 0.7891 0.068 Uiso 1 1 calc R U . . .
C16 C 0.1538(2) 1.00059(16) 0.86186(18) 0.0394(4) Uani 1 1 d . . . . .
H16 H 0.1456 0.9813 0.7735 0.059 Uiso 1 1 calc R U . . .
H17 H 0.2559 1.0572 0.9050 0.059 Uiso 1 1 calc R U . . .
H18 H 0.0671 1.0427 0.8680 0.059 Uiso 1 1 calc R U . . .
C17 C 0.2055(2) 0.47087(15) 0.47767(17) 0.0347(4) Uani 1 1 d . . . . .
H19 H 0.1598 0.5023 0.5403 0.052 Uiso 1 1 calc R U . . .
H20 H 0.3016 0.4396 0.5198 0.052 Uiso 1 1 calc R U . . .
H21 H 0.1280 0.4012 0.4206 0.052 Uiso 1 1 calc R U . . .
C18 C 0.0792(2) 0.65021(19) 0.28648(17) 0.0453(4) Uani 1 1 d . . . . .
H22 H 0.0084 0.5753 0.2326 0.068 Uiso 1 1 calc R U . . .
H23 H 0.1115 0.7134 0.2345 0.068 Uiso 1 1 calc R U . . .
H24 H 0.0234 0.6876 0.3385 0.068 Uiso 1 1 calc R U . . .


_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
N1 N2 1.2558(17) . ?
N1 C1 1.4422(19) . ?
N2 C8 1.4474(18) . ?
F1 Si1 1.6107(10) . ?
F2 Si2 1.6095(10) . ?
Si1 C15 1.8404(18) . ?
Si1 C16 1.8426(18) . ?
Si1 C2 1.8713(15) . ?
Si2 C18 1.8410(18) . ?
Si2 C17 1.8476(17) . ?
Si2 C9 1.8693(15) . ?
C1 C6 1.395(2) . ?
C1 C2 1.402(2) . ?
C2 C3 1.397(2) . ?
C3 C4 1.391(2) . ?
C3 H1 0.9500 . ?
C4 C5 1.390(2) . ?
C4 C7 1.510(2) . ?
C5 C6 1.385(2) . ?
C5 H2 0.9500 . ?
C6 H3 0.9500 . ?
C7 H7 0.9800 . ?
C7 H8 0.9800 . ?
C7 H9 0.9800 . ?
C8 C13 1.388(2) . ?
C8 C9 1.400(2) . ?
C9 C10 1.399(2) . ?
C10 C11 1.396(2) . ?
C10 H4 0.9500 . ?
C11 C12 1.386(2) . ?
C11 C14 1.511(2) . ?
C12 C13 1.386(2) . ?
C12 H5 0.9500 . ?
C13 H6 0.9500 . ?
C14 H10 0.9800 . ?
C14 H11 0.9800 . ?
C14 H12 0.9800 . ?
C15 H13 0.9800 . ?
C15 H14 0.9800 . ?
C15 H15 0.9800 . ?
C16 H16 0.9800 . ?
C16 H17 0.9800 . ?
C16 H18 0.9800 . ?
C17 H19 0.9800 . ?
C17 H20 0.9800 . ?
C17 H21 0.9800 . ?
C18 H22 0.9800 . ?
C18 H23 0.9800 . ?
C18 H24 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
N2 N1 C1 123.48(12) . . ?
N1 N2 C8 122.47(12) . . ?
F1 Si1 C15 106.21(8) . . ?
F1 Si1 C16 106.50(8) . . ?
C15 Si1 C16 113.64(9) . . ?
F1 Si1 C2 103.57(6) . . ?
C15 Si1 C2 114.30(8) . . ?
C16 Si1 C2 111.62(7) . . ?
F2 Si2 C18 107.54(8) . . ?
F2 Si2 C17 107.03(7) . . ?
C18 Si2 C17 112.44(9) . . ?
F2 Si2 C9 104.11(6) . . ?
C18 Si2 C9 112.86(8) . . ?
C17 Si2 C9 112.23(7) . . ?
C6 C1 C2 121.28(14) . . ?
C6 C1 N1 123.83(13) . . ?
C2 C1 N1 114.36(12) . . ?
C3 C2 C1 117.46(14) . . ?
C3 C2 Si1 121.89(11) . . ?
C1 C2 Si1 120.62(11) . . ?
C4 C3 C2 122.23(14) . . ?
C4 C3 H1 118.9 . . ?
C2 C3 H1 118.9 . . ?
C5 C4 C3 118.44(14) . . ?
C5 C4 C7 120.69(15) . . ?
C3 C4 C7 120.87(15) . . ?
C6 C5 C4 121.30(14) . . ?
C6 C5 H2 119.4 . . ?
C4 C5 H2 119.4 . . ?
C5 C6 C1 119.17(14) . . ?
C5 C6 H3 120.4 . . ?
C1 C6 H3 120.4 . . ?
C4 C7 H7 109.5 . . ?
C4 C7 H8 109.5 . . ?
H7 C7 H8 109.5 . . ?
C4 C7 H9 109.5 . . ?
H7 C7 H9 109.5 . . ?
H8 C7 H9 109.5 . . ?
C13 C8 C9 121.69(13) . . ?
C13 C8 N2 121.40(13) . . ?
C9 C8 N2 116.52(12) . . ?
C10 C9 C8 117.06(13) . . ?
C10 C9 Si2 120.85(11) . . ?
C8 C9 Si2 122.04(11) . . ?
C11 C10 C9 122.40(14) . . ?
C11 C10 H4 118.8 . . ?
C9 C10 H4 118.8 . . ?
C12 C11 C10 118.27(14) . . ?
C12 C11 C14 121.47(14) . . ?
C10 C11 C14 120.26(15) . . ?
C11 C12 C13 121.23(14) . . ?
C11 C12 H5 119.4 . . ?
C13 C12 H5 119.4 . . ?
C12 C13 C8 119.30(14) . . ?
C12 C13 H6 120.3 . . ?
C8 C13 H6 120.3 . . ?
C11 C14 H10 109.5 . . ?
C11 C14 H11 109.5 . . ?
H10 C14 H11 109.5 . . ?
C11 C14 H12 109.5 . . ?
H10 C14 H12 109.5 . . ?
H11 C14 H12 109.5 . . ?
Si1 C15 H13 109.5 . . ?
Si1 C15 H14 109.5 . . ?
H13 C15 H14 109.5 . . ?
Si1 C15 H15 109.5 . . ?
H13 C15 H15 109.5 . . ?
H14 C15 H15 109.5 . . ?
Si1 C16 H16 109.5 . . ?
Si1 C16 H17 109.5 . . ?
H16 C16 H17 109.5 . . ?
Si1 C16 H18 109.5 . . ?
H16 C16 H18 109.5 . . ?
H17 C16 H18 109.5 . . ?
Si2 C17 H19 109.5 . . ?
Si2 C17 H20 109.5 . . ?
H19 C17 H20 109.5 . . ?
Si2 C17 H21 109.5 . . ?
H19 C17 H21 109.5 . . ?
H20 C17 H21 109.5 . . ?
Si2 C18 H22 109.5 . . ?
Si2 C18 H23 109.5 . . ?
H22 C18 H23 109.5 . . ?
Si2 C18 H24 109.5 . . ?
H22 C18 H24 109.5 . . ?
H23 C18 H24 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
C1 N1 N2 C8 -8.7(2) . . . . ?
N2 N1 C1 C6 -43.5(2) . . . . ?
N2 N1 C1 C2 144.79(14) . . . . ?
C6 C1 C2 C3 3.9(2) . . . . ?
N1 C1 C2 C3 175.88(12) . . . . ?
C6 C1 C2 Si1 -177.96(11) . . . . ?
N1 C1 C2 Si1 -5.99(17) . . . . ?
F1 Si1 C2 C3 1.79(14) . . . . ?
C15 Si1 C2 C3 -113.30(14) . . . . ?
C16 Si1 C2 C3 115.99(13) . . . . ?
F1 Si1 C2 C1 -176.25(11) . . . . ?
C15 Si1 C2 C1 68.65(14) . . . . ?
C16 Si1 C2 C1 -62.05(14) . . . . ?
C1 C2 C3 C4 -3.3(2) . . . . ?
Si1 C2 C3 C4 178.63(11) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C2 C3 C4 C7 -178.86(14) . . . . ?
C3 C4 C5 C6 1.9(2) . . . . ?
C7 C4 C5 C6 -178.80(14) . . . . ?
C4 C5 C6 C1 -1.3(2) . . . . ?
C2 C1 C6 C5 -1.7(2) . . . . ?
N1 C1 C6 C5 -172.92(13) . . . . ?
N1 N2 C8 C13 -55.65(19) . . . . ?
N1 N2 C8 C9 131.39(14) . . . . ?
C13 C8 C9 C10 2.8(2) . . . . ?
N2 C8 C9 C10 175.70(12) . . . . ?
C13 C8 C9 Si2 -179.86(11) . . . . ?
N2 C8 C9 Si2 -6.92(17) . . . . ?
F2 Si2 C9 C10 5.30(13) . . . . ?
C18 Si2 C9 C10 -111.00(13) . . . . ?
C17 Si2 C9 C10 120.70(12) . . . . ?
F2 Si2 C9 C8 -171.98(11) . . . . ?
C18 Si2 C9 C8 71.72(14) . . . . ?
C17 Si2 C9 C8 -56.58(13) . . . . ?
C8 C9 C10 C11 -2.0(2) . . . . ?
Si2 C9 C10 C11 -179.37(11) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
C9 C10 C11 C14 -179.79(13) . . . . ?
C10 C11 C12 C13 1.3(2) . . . . ?
C14 C11 C12 C13 -178.94(14) . . . . ?
C11 C12 C13 C8 -0.5(2) . . . . ?
C9 C8 C13 C12 -1.6(2) . . . . ?
N2 C8 C13 C12 -174.20(13) . . . . ?

_refine_diff_density_max         0.397
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.050

_shelxl_version_number           2014/6

