# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_audit_block_doi                 10.5517/ccdc.csd.cc207h2v
_database_code_depnum_ccdc_archive 'CCDC 1854236'
_audit_update_record             
;
2018-07-06 deposited with the CCDC.
2018-09-05 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            'Organic Compound'
_chemical_formula_moiety         'C42 H50 O2 Si2'
_chemical_formula_sum            'C42 H50 O2 Si2'
_chemical_formula_iupac          ?
_chemical_formula_weight         643.00

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6019(6)
_cell_length_b                   7.7795(7)
_cell_length_c                   17.7908(15)
_cell_angle_alpha                94.036(5)
_cell_angle_beta                 92.577(5)
_cell_angle_gamma                114.867(4)
_cell_volume                     948.98(14)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    125
_cell_measurement_theta_min      3.0335
_cell_measurement_theta_max      22.8899
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.467
_exptl_crystal_size_mid          0.358
_exptl_crystal_size_min          0.038
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             346

_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'

_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            13766
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_refine_special_details          
;
;

_reflns_number_total             3303
_reflns_number_gt                2677
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0860
_refine_ls_wR_factor_gt          0.2596
_refine_ls_wR_factor_ref         0.2746
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_number_reflns         3303
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1844P)²+0.3694P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.978
_refine_diff_density_min         -0.381
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXTL V6.14 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL V6.14 (Bruker AXS)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  
'PLATON V1.16 (Spek, 2009), SHELXTL V6.14 (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.7272(5) 0.9046(5) 0.2577(2) 0.0621(9) Uani d . . . 1 . .
C C2 0.7265(5) 0.7978(5) 0.30350(19) 0.0549(8) Uani d . . . 1 . .
C C3 0.7119(4) 0.6545(4) 0.35229(16) 0.0472(7) Uani d . . . 1 . .
C C4 0.5288(4) 0.5377(4) 0.37605(17) 0.0459(7) Uani d . . . 1 . .
H H4 0.4211 0.5622 0.3654 0.055 Uiso calc U . R 1 . .
C C5 0.5133(4) 0.3883(4) 0.41496(15) 0.0408(7) Uani d . . . 1 . .
C C6 0.3357(4) 0.2387(4) 0.44296(16) 0.0418(7) Uani d . . . 1 . .
C C7 0.4045(4) 0.1025(4) 0.47560(15) 0.0376(6) Uani d . . . 1 . .
C C8 0.2954(4) -0.0628(4) 0.50750(15) 0.0398(7) Uani d . . . 1 . .
H H8 0.1632 -0.1024 0.5126 0.048 Uiso calc U . R 1 . .
C C9 0.6047(4) 0.1670(4) 0.46827(14) 0.0377(7) Uani d . . . 1 . .
C C10 0.6715(4) 0.3447(4) 0.43131(15) 0.0399(7) Uani d . . . 1 . .
C C11 0.8544(4) 0.4633(4) 0.41109(16) 0.0462(7) Uani d . . . 1 . .
H H11 0.9623 0.4405 0.4235 0.055 Uiso calc U . R 1 . .
C C12 0.8716(4) 0.6160(4) 0.37199(17) 0.0488(8) Uani d . . . 1 . .
H H12 0.9935 0.6962 0.3582 0.059 Uiso calc U . R 1 . .
C C13 0.5339(8) 1.1513(8) 0.2145(3) 0.0950(15) Uani d . . . 1 . .
H H13 0.6115 1.2564 0.2528 0.114 Uiso calc U . R 1 . .
C C14 0.4675(14) 1.2406(16) 0.1519(6) 0.187(4) Uani d . . . 1 . .
H H14A 0.4279 1.1549 0.1065 0.281 Uiso calc U . R 1 . .
H H14B 0.5729 1.3581 0.1427 0.281 Uiso calc U . R 1 . .
H H14C 0.3598 1.2649 0.1671 0.281 Uiso calc U . R 1 . .
C C15 0.3593(7) 1.0204(8) 0.2529(3) 0.0969(15) Uani d . . . 1 . .
H H15A 0.2923 1.0915 0.2732 0.145 Uiso calc U . R 1 . .
H H15B 0.4024 0.9675 0.2931 0.145 Uiso calc U . R 1 . .
H H15C 0.2728 0.9194 0.2166 0.145 Uiso calc U . R 1 . .
C C16 0.9538(8) 1.2335(7) 0.1673(3) 0.0881(13) Uani d . . . 1 . .
H H16 1.0329 1.1639 0.1566 0.106 Uiso calc U . R 1 . .
C C17 0.9581(11) 1.3395(11) 0.0996(4) 0.146(3) Uani d . . . 1 . .
H H17A 0.8932 1.4204 0.109 0.218 Uiso calc U . R 1 . .
H H17B 0.8931 1.2502 0.0563 0.218 Uiso calc U . R 1 . .
H H17C 1.0906 1.4156 0.0901 0.218 Uiso calc U . R 1 . .
C C18 1.0481(7) 1.3607(8) 0.2385(3) 0.0990(16) Uani d . . . 1 . .
H H18A 1.1814 1.441 0.2316 0.149 Uiso calc U . R 1 . .
H H18B 1.0427 1.2845 0.2793 0.149 Uiso calc U . R 1 . .
H H18C 0.9807 1.4382 0.2502 0.149 Uiso calc U . R 1 . .
C C19 0.6273(11) 0.8885(8) 0.0928(3) 0.117(2) Uani d . . . 1 . .
H H19 0.6184 0.9648 0.0525 0.14 Uiso calc U . R 1 . .
C C20 0.7550(19) 0.7994(14) 0.0705(4) 0.204(5) Uani d . . . 1 . .
H H20A 0.7313 0.6922 0.0988 0.306 Uiso calc U . R 1 . .
H H20B 0.8883 0.8901 0.0807 0.306 Uiso calc U . R 1 . .
H H20C 0.7292 0.7574 0.0175 0.306 Uiso calc U . R 1 . .
C C21 0.4230(14) 0.7215(10) 0.0958(5) 0.172(4) Uani d . . . 1 . .
H H21A 0.3955 0.6319 0.0521 0.258 Uiso calc U . R 1 . .
H H21B 0.3262 0.7704 0.0965 0.258 Uiso calc U . R 1 . .
H H21C 0.4214 0.6592 0.1407 0.258 Uiso calc U . R 1 . .
O O1 0.1739(3) 0.2297(3) 0.43947(14) 0.0584(7) Uani d . . . 1 . .
Si Si1 0.69929(15) 1.04317(13) 0.18294(5) 0.0566(4) Uani d . . . 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.203(5) ?
C1 Si1 . 1.828(4) ?
C2 C3 . 1.432(4) ?
C3 C12 . 1.403(5) ?
C3 C4 . 1.409(4) ?
C4 C5 . 1.360(4) ?
C4 H4 . 0.93 ?
C5 C10 . 1.404(4) ?
C5 C6 . 1.499(4) ?
C6 O1 . 1.200(3) ?
C6 C7 . 1.503(4) ?
C7 C8 . 1.382(4) ?
C7 C9 . 1.404(4) ?
C8 C9 2_656 1.399(4) ?
C8 H8 . 0.93 ?
C9 C8 2_656 1.399(4) ?
C9 C10 . 1.473(4) ?
C10 C11 . 1.388(4) ?
C11 C12 . 1.380(4) ?
C11 H11 . 0.93 ?
C12 H12 . 0.93 ?
C13 C15 . 1.519(7) ?
C13 C14 . 1.527(8) ?
C13 Si1 . 1.868(5) ?
C13 H13 . 0.98 ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
C16 C18 . 1.497(7) ?
C16 C17 . 1.502(7) ?
C16 Si1 . 1.926(5) ?
C16 H16 . 0.98 ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
C19 C20 . 1.464(10) ?
C19 C21 . 1.556(10) ?
C19 Si1 . 1.847(5) ?
C19 H19 . 0.98 ?
C20 H20A . 0.96 ?
C20 H20B . 0.96 ?
C20 H20C . 0.96 ?
C21 H21A . 0.96 ?
C21 H21B . 0.96 ?
C21 H21C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 Si1 . . 172.8(3) ?
C1 C2 C3 . . 173.9(4) ?
C12 C3 C4 . . 118.7(3) ?
C12 C3 C2 . . 121.9(3) ?
C4 C3 C2 . . 119.2(3) ?
C5 C4 C3 . . 118.4(3) ?
C5 C4 H4 . . 120.8 ?
C3 C4 H4 . . 120.8 ?
C4 C5 C10 . . 122.6(3) ?
C4 C5 C6 . . 128.9(3) ?
C10 C5 C6 . . 108.3(2) ?
O1 C6 C5 . . 127.3(3) ?
O1 C6 C7 . . 127.8(3) ?
C5 C6 C7 . . 104.9(2) ?
C8 C7 C9 . . 123.0(3) ?
C8 C7 C6 . . 127.9(2) ?
C9 C7 C6 . . 109.1(2) ?
C7 C8 C9 . 2_656 116.2(2) ?
C7 C8 H8 . . 121.9 ?
C9 C8 H8 2_656 . 121.9 ?
C8 C9 C7 2_656 . 120.7(2) ?
C8 C9 C10 2_656 . 131.1(2) ?
C7 C9 C10 . . 108.1(2) ?
C11 C10 C5 . . 119.5(3) ?
C11 C10 C9 . . 131.0(3) ?
C5 C10 C9 . . 109.5(2) ?
C12 C11 C10 . . 118.1(3) ?
C12 C11 H11 . . 120.9 ?
C10 C11 H11 . . 120.9 ?
C11 C12 C3 . . 122.5(3) ?
C11 C12 H12 . . 118.8 ?
C3 C12 H12 . . 118.8 ?
C15 C13 C14 . . 109.9(5) ?
C15 C13 Si1 . . 115.0(4) ?
C14 C13 Si1 . . 113.3(4) ?
C15 C13 H13 . . 106.0 ?
C14 C13 H13 . . 106.0 ?
Si1 C13 H13 . . 106.0 ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C13 C15 H15A . . 109.5 ?
C13 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C13 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C18 C16 C17 . . 113.6(5) ?
C18 C16 Si1 . . 111.0(3) ?
C17 C16 Si1 . . 114.0(4) ?
C18 C16 H16 . . 105.8 ?
C17 C16 H16 . . 105.8 ?
Si1 C16 H16 . . 105.8 ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C16 C18 H18A . . 109.5 ?
C16 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C16 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C20 C19 C21 . . 105.6(7) ?
C20 C19 Si1 . . 116.8(6) ?
C21 C19 Si1 . . 110.2(5) ?
C20 C19 H19 . . 108.0 ?
C21 C19 H19 . . 108.0 ?
Si1 C19 H19 . . 108.0 ?
C19 C20 H20A . . 109.5 ?
C19 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C19 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C19 C21 H21A . . 109.5 ?
C19 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C19 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C1 Si1 C19 . . 108.1(2) ?
C1 Si1 C13 . . 107.70(19) ?
C19 Si1 C13 . . 117.6(3) ?
C1 Si1 C16 . . 107.9(2) ?
C19 Si1 C16 . . 103.0(3) ?
C13 Si1 C16 . . 112.1(2) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C12 C3 C4 C5 . . . . -2.2(4) ?
C2 C3 C4 C5 . . . . 172.4(3) ?
C3 C4 C5 C10 . . . . -0.9(4) ?
C3 C4 C5 C6 . . . . -176.7(3) ?
C4 C5 C6 O1 . . . . -4.4(5) ?
C10 C5 C6 O1 . . . . 179.4(3) ?
C4 C5 C6 C7 . . . . 175.2(3) ?
C10 C5 C6 C7 . . . . -1.1(3) ?
O1 C6 C7 C8 . . . . 0.9(5) ?
C5 C6 C7 C8 . . . . -178.6(3) ?
O1 C6 C7 C9 . . . . -179.9(3) ?
C5 C6 C7 C9 . . . . 0.6(3) ?
C9 C7 C8 C9 . . . 2_656 -0.9(4) ?
C6 C7 C8 C9 . . . 2_656 178.2(3) ?
C8 C7 C9 C8 . . . 2_656 1.0(4) ?
C6 C7 C9 C8 . . . 2_656 -178.3(2) ?
C8 C7 C9 C10 . . . . 179.4(2) ?
C6 C7 C9 C10 . . . . 0.1(3) ?
C4 C5 C10 C11 . . . . 3.7(4) ?
C6 C5 C10 C11 . . . . -179.8(2) ?
C4 C5 C10 C9 . . . . -175.4(3) ?
C6 C5 C10 C9 . . . . 1.2(3) ?
C8 C9 C10 C11 2_656 . . . -1.6(5) ?
C7 C9 C10 C11 . . . . -179.7(3) ?
C8 C9 C10 C5 2_656 . . . 177.3(3) ?
C7 C9 C10 C5 . . . . -0.8(3) ?
C5 C10 C11 C12 . . . . -3.1(4) ?
C9 C10 C11 C12 . . . . 175.7(3) ?
C10 C11 C12 C3 . . . . 0.0(5) ?
C4 C3 C12 C11 . . . . 2.7(5) ?
C2 C3 C12 C11 . . . . -171.7(3) ?
C20 C19 Si1 C1 . . . . -55.6(6) ?
C21 C19 Si1 C1 . . . . 64.9(6) ?
C20 C19 Si1 C13 . . . . -177.7(6) ?
C21 C19 Si1 C13 . . . . -57.3(6) ?
C20 C19 Si1 C16 . . . . 58.5(6) ?
C21 C19 Si1 C16 . . . . 179.0(5) ?
C15 C13 Si1 C1 . . . . -41.7(5) ?
C14 C13 Si1 C1 . . . . -169.3(6) ?
C15 C13 Si1 C19 . . . . 80.7(5) ?
C14 C13 Si1 C19 . . . . -46.9(7) ?
C15 C13 Si1 C16 . . . . -160.3(4) ?
C14 C13 Si1 C16 . . . . 72.1(6) ?



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc207h3w
_database_code_depnum_ccdc_archive 'CCDC 1854237'
_audit_update_record             
;
2018-07-06 deposited with the CCDC.
2018-09-05 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            'Organic Compound'
_chemical_formula_moiety         'C48 H50 N4 Si2'
_chemical_formula_sum            'C48 H50 N4 Si2'
_chemical_formula_iupac          ?
_chemical_formula_weight         739.10

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   39.755(5)
_cell_length_b                   10.0294(12)
_cell_length_c                   11.4351(14)
_cell_angle_alpha                90
_cell_angle_beta                 102.874(8)
_cell_angle_gamma                90
_cell_volume                     4444.8(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2806
_cell_measurement_theta_min      2.5710
_cell_measurement_theta_max      23.4121
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.032
_exptl_crystal_density_diffrn    1.104
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1576

_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'

_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            16272
_diffrn_reflns_av_R_equivalents  0.0967
_diffrn_reflns_av_unetI/netI     0.0833
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10

_refine_special_details          
;
;

_reflns_number_total             3918
_reflns_number_gt                1782
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.2020
_refine_ls_R_factor_gt           0.1097
_refine_ls_wR_factor_gt          0.3031
_refine_ls_wR_factor_ref         0.3730
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.034
_refine_ls_number_reflns         3918
_refine_ls_number_parameters     250
_refine_ls_number_restraints     19
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1917P)²+6.5584P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.234
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXTL V6.14 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL V6.14 (Bruker AXS)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  
'PLATON V1.16 (Spek, 2009), SHELXTL V6.14 (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2590(3) 0.227(2) 0.2308(18) 0.289(11) Uani d . . . 1 . .
H H1A 0.2567 0.1314 0.2276 0.434 Uiso calc U . R 1 . .
H H1B 0.259 0.2603 0.1522 0.434 Uiso calc U . R 1 . .
H H1C 0.2401 0.2649 0.2587 0.434 Uiso calc U . R 1 . .
C C2 0.2907(4) 0.229(2) 0.4398(12) 0.258(7) Uani d U . D 1 . .
H H2A 0.2726 0.2785 0.4639 0.387 Uiso calc U . R 1 . .
H H2B 0.3125 0.2535 0.49 0.387 Uiso calc U . R 1 . .
H H2C 0.2868 0.1355 0.4475 0.387 Uiso calc U . R 1 . .
C C3 0.2907(3) 0.2614(16) 0.3111(11) 0.200(6) Uani d U . D 1 . .
H H3 0.2894 0.359 0.3108 0.24 Uiso calc U . R 1 . .
C C4 0.3380(3) 0.5009(14) 0.1847(12) 0.190(5) Uani d . . . 1 . .
H H4A 0.3411 0.5585 0.1208 0.285 Uiso calc U . R 1 . .
H H4B 0.3568 0.5134 0.2529 0.285 Uiso calc U . R 1 . .
H H4C 0.3166 0.522 0.2064 0.285 Uiso calc U . R 1 . .
C C5 0.3373(3) 0.3553(13) 0.1432(9) 0.151(4) Uani d . . . 1 . .
H H5 0.3608 0.3384 0.1333 0.181 Uiso calc U . R 1 . .
C C6 0.3162(5) 0.3347(18) 0.0269(11) 0.275(10) Uani d . . . 1 . .
H H6A 0.2928 0.359 0.0269 0.412 Uiso calc U . R 1 . .
H H6B 0.317 0.2425 0.0053 0.412 Uiso calc U . R 1 . .
H H6C 0.3244 0.3889 -0.0301 0.412 Uiso calc U . R 1 . .
C C7 0.3316(4) -0.0448(15) 0.3051(14) 0.225(6) Uani d U . . 1 . .
H H7A 0.3502 -0.1076 0.3133 0.338 Uiso calc U . R 1 . .
H H7B 0.31 -0.0911 0.2833 0.338 Uiso calc U . R 1 . .
H H7C 0.3331 0.0006 0.38 0.338 Uiso calc U . R 1 . .
C C8 0.3342(3) 0.0572(11) 0.2073(10) 0.141(3) Uani d U . . 1 . .
H H8 0.3152 0.0419 0.1376 0.169 Uiso calc U . R 1 . .
C C9 0.3652(3) 0.0239(13) 0.1771(13) 0.202(5) Uani d U . . 1 . .
H H9A 0.3833 0.021 0.2484 0.303 Uiso calc U . R 1 . .
H H9B 0.3706 0.0897 0.1232 0.303 Uiso calc U . R 1 . .
H H9C 0.363 -0.0618 0.1388 0.303 Uiso calc U . R 1 . .
C C10 0.36740(19) 0.2651(7) 0.3870(7) 0.090(2) Uani d . . . 1 . .
C C11 0.39035(19) 0.2908(7) 0.4719(7) 0.088(2) Uani d . . . 1 . .
C C12 0.41605(16) 0.3205(6) 0.5773(6) 0.0772(17) Uani d . . . 1 . .
C C13 0.43281(17) 0.2166(6) 0.6500(7) 0.0845(19) Uani d . . . 1 . .
H H13 0.4289 0.1289 0.6242 0.101 Uiso calc U . R 1 . .
C C14 0.45490(17) 0.2419(5) 0.7582(6) 0.0767(18) Uani d . . . 1 . .
H H14 0.4654 0.172 0.8062 0.092 Uiso calc U . R 1 . .
C C15 0.46134(13) 0.3704(5) 0.7944(5) 0.0627(15) Uani d . . . 1 . .
C C16 0.48231(13) 0.4246(5) 0.9045(5) 0.0626(15) Uani d . . . 1 . .
C C17 0.48029(13) 0.5653(5) 0.9008(5) 0.0614(15) Uani d . . . 1 . .
C C18 0.45851(13) 0.6027(5) 0.7844(5) 0.0649(15) Uani d . . . 1 . .
C C19 0.44622(14) 0.4767(5) 0.7209(6) 0.0640(15) Uani d . . . 1 . .
C C20 0.4630(2) 0.8431(7) 0.8092(8) 0.119(3) Uani d . . . 1 . .
C C21 0.45148(15) 0.7298(5) 0.7424(6) 0.0754(18) Uani d . . . 1 . .
C C22 0.43310(18) 0.7551(6) 0.6208(8) 0.087(2) Uani d . . . 1 . .
C C23 0.50218(14) 0.3589(5) 1.0040(6) 0.0682(16) Uani d . . . 1 . .
H H23 0.5036 0.2663 1.0061 0.082 Uiso calc U . R 1 . .
C C24 0.42347(14) 0.4517(6) 0.6129(6) 0.0718(16) Uani d . . . 1 . .
H H007 0.4133 0.5218 0.5646 0.086 Uiso calc U . R 1 . .
N N1 0.4192(2) 0.7822(7) 0.5250(7) 0.127(3) Uani d . . . 1 . .
N N2 0.4729(3) 0.9357(7) 0.8629(9) 0.188(5) Uani d . . . 1 . .
Si Si1 0.33115(5) 0.2316(2) 0.26221(18) 0.0916(8) Uani d . . . 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C3 . 1.425(15) ?
C1 H1A . 0.96 ?
C1 H1B . 0.96 ?
C1 H1C . 0.96 ?
C2 C3 . 1.506(9) ?
C2 H2A . 0.96 ?
C2 H2B . 0.96 ?
C2 H2C . 0.96 ?
C3 Si1 . 1.843(11) ?
C3 H3 . 0.98 ?
C4 C5 . 1.534(16) ?
C4 H4A . 0.96 ?
C4 H4B . 0.96 ?
C4 H4C . 0.96 ?
C5 C6 . 1.420(16) ?
C5 Si1 . 1.897(11) ?
C5 H5 . 0.98 ?
C6 H6A . 0.96 ?
C6 H6B . 0.96 ?
C6 H6C . 0.96 ?
C7 C8 . 1.536(16) ?
C7 H7A . 0.96 ?
C7 H7B . 0.96 ?
C7 H7C . 0.96 ?
C8 C9 . 1.393(14) ?
C8 Si1 . 1.871(10) ?
C8 H8 . 0.98 ?
C9 H9A . 0.96 ?
C9 H9B . 0.96 ?
C9 H9C . 0.96 ?
C10 C11 . 1.202(9) ?
C10 Si1 . 1.819(8) ?
C11 C12 . 1.427(10) ?
C12 C24 . 1.390(8) ?
C12 C13 . 1.404(9) ?
C13 C14 . 1.372(9) ?
C13 H13 . 0.93 ?
C14 C15 . 1.361(7) ?
C14 H14 . 0.93 ?
C15 C19 . 1.407(7) ?
C15 C16 . 1.451(8) ?
C16 C23 . 1.397(8) ?
C16 C17 . 1.413(7) ?
C17 C23 5_667 1.383(8) ?
C17 C18 . 1.466(8) ?
C18 C21 . 1.369(7) ?
C18 C19 . 1.484(8) ?
C19 C24 . 1.382(8) ?
C20 N2 . 1.135(10) ?
C20 C21 . 1.389(10) ?
C21 C22 . 1.443(10) ?
C22 N1 . 1.145(9) ?
C23 C17 5_667 1.383(8) ?
C23 H23 . 0.93 ?
C24 H007 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 C1 H1A . . 109.5 ?
C3 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C3 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C3 C2 H2A . . 109.5 ?
C3 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C3 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
C1 C3 C2 . . 112.6(13) ?
C1 C3 Si1 . . 118.0(11) ?
C2 C3 Si1 . . 116.9(9) ?
C1 C3 H3 . . 101.9 ?
C2 C3 H3 . . 101.9 ?
Si1 C3 H3 . . 101.9 ?
C5 C4 H4A . . 109.5 ?
C5 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C5 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C6 C5 C4 . . 113.2(11) ?
C6 C5 Si1 . . 115.6(11) ?
C4 C5 Si1 . . 113.4(8) ?
C6 C5 H5 . . 104.3 ?
C4 C5 H5 . . 104.3 ?
Si1 C5 H5 . . 104.3 ?
C5 C6 H6A . . 109.5 ?
C5 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C5 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C8 C7 H7A . . 109.5 ?
C8 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C8 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C9 C8 C7 . . 103.1(11) ?
C9 C8 Si1 . . 115.7(8) ?
C7 C8 Si1 . . 111.0(9) ?
C9 C8 H8 . . 108.9 ?
C7 C8 H8 . . 108.9 ?
Si1 C8 H8 . . 108.9 ?
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 ?
C11 C10 Si1 . . 176.9(7) ?
C10 C11 C12 . . 176.4(8) ?
C24 C12 C13 . . 119.2(6) ?
C24 C12 C11 . . 120.7(6) ?
C13 C12 C11 . . 120.1(6) ?
C14 C13 C12 . . 121.3(6) ?
C14 C13 H13 . . 119.3 ?
C12 C13 H13 . . 119.3 ?
C15 C14 C13 . . 119.3(6) ?
C15 C14 H14 . . 120.3 ?
C13 C14 H14 . . 120.3 ?
C14 C15 C19 . . 120.6(6) ?
C14 C15 C16 . . 130.7(5) ?
C19 C15 C16 . . 108.7(5) ?
C23 C16 C17 . . 120.9(5) ?
C23 C16 C15 . . 129.8(5) ?
C17 C16 C15 . . 109.3(5) ?
C23 C17 C16 5_667 . 120.7(5) ?
C23 C17 C18 5_667 . 131.8(5) ?
C16 C17 C18 . . 107.5(5) ?
C21 C18 C17 . . 126.1(5) ?
C21 C18 C19 . . 127.0(6) ?
C17 C18 C19 . . 106.9(4) ?
C24 C19 C15 . . 120.3(5) ?
C24 C19 C18 . . 132.1(5) ?
C15 C19 C18 . . 107.6(5) ?
N2 C20 C21 . . 178.6(12) ?
C18 C21 C20 . . 123.6(6) ?
C18 C21 C22 . . 121.5(6) ?
C20 C21 C22 . . 114.8(5) ?
N1 C22 C21 . . 176.3(8) ?
C17 C23 C16 5_667 . 118.4(5) ?
C17 C23 H23 5_667 . 120.8 ?
C16 C23 H23 . . 120.8 ?
C19 C24 C12 . . 119.2(5) ?
C19 C24 H007 . . 120.4 ?
C12 C24 H007 . . 120.4 ?
C10 Si1 C3 . . 109.0(4) ?
C10 Si1 C8 . . 109.7(4) ?
C3 Si1 C8 . . 112.3(6) ?
C10 Si1 C5 . . 103.7(5) ?
C3 Si1 C5 . . 111.8(6) ?
C8 Si1 C5 . . 110.0(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C24 C12 C13 C14 . . . . 3.5(10) ?
C11 C12 C13 C14 . . . . -173.0(6) ?
C12 C13 C14 C15 . . . . -1.6(10) ?
C13 C14 C15 C19 . . . . -1.5(9) ?
C13 C14 C15 C16 . . . . 177.6(6) ?
C14 C15 C16 C23 . . . . 0.8(10) ?
C19 C15 C16 C23 . . . . -180.0(5) ?
C14 C15 C16 C17 . . . . -178.9(6) ?
C19 C15 C16 C17 . . . . 0.3(6) ?
C23 C16 C17 C23 . . . 5_667 -0.4(9) ?
C15 C16 C17 C23 . . . 5_667 179.4(5) ?
C23 C16 C17 C18 . . . . 178.4(5) ?
C15 C16 C17 C18 . . . . -1.9(6) ?
C23 C17 C18 C21 5_667 . . . 2.2(10) ?
C16 C17 C18 C21 . . . . -176.4(6) ?
C23 C17 C18 C19 5_667 . . . -178.8(5) ?
C16 C17 C18 C19 . . . . 2.7(6) ?
C14 C15 C19 C24 . . . . 2.7(8) ?
C16 C15 C19 C24 . . . . -176.6(5) ?
C14 C15 C19 C18 . . . . -179.3(5) ?
C16 C15 C19 C18 . . . . 1.4(6) ?
C21 C18 C19 C24 . . . . -5.8(10) ?
C17 C18 C19 C24 . . . . 175.2(6) ?
C21 C18 C19 C15 . . . . 176.6(6) ?
C17 C18 C19 C15 . . . . -2.5(6) ?
C17 C18 C21 C20 . . . . -3.6(11) ?
C19 C18 C21 C20 . . . . 177.6(7) ?
C17 C18 C21 C22 . . . . 172.4(6) ?
C19 C18 C21 C22 . . . . -6.5(10) ?
C17 C16 C23 C17 . . . 5_667 0.4(9) ?
C15 C16 C23 C17 . . . 5_667 -179.3(5) ?
C15 C19 C24 C12 . . . . -0.7(8) ?
C18 C19 C24 C12 . . . . -178.1(6) ?
C13 C12 C24 C19 . . . . -2.3(9) ?
C11 C12 C24 C19 . . . . 174.2(6) ?
C1 C3 Si1 C10 . . . . -173.1(13) ?
C2 C3 Si1 C10 . . . . -33.8(14) ?
C1 C3 Si1 C8 . . . . -51.4(15) ?
C2 C3 Si1 C8 . . . . 87.9(13) ?
C1 C3 Si1 C5 . . . . 72.9(15) ?
C2 C3 Si1 C5 . . . . -147.8(12) ?
C9 C8 Si1 C10 . . . . -54.1(11) ?
C7 C8 Si1 C10 . . . . 63.0(10) ?
C9 C8 Si1 C3 . . . . -175.4(10) ?
C7 C8 Si1 C3 . . . . -58.3(10) ?
C9 C8 Si1 C5 . . . . 59.3(11) ?
C7 C8 Si1 C5 . . . . 176.4(9) ?
C6 C5 Si1 C10 . . . . 168.6(10) ?
C4 C5 Si1 C10 . . . . -58.3(9) ?
C6 C5 Si1 C3 . . . . -74.2(12) ?
C4 C5 Si1 C3 . . . . 59.0(10) ?
C6 C5 Si1 C8 . . . . 51.4(12) ?
C4 C5 Si1 C8 . . . . -175.5(8) ?



