# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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. 
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data_Ph2Pen
_database_code_depnum_ccdc_archive 'CCDC 1511836'
_audit_update_record             
;
2016-10-27 deposited with the CCDC.
2016-11-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
5-(tert-butyldimethylsilyl)-10-(trimethylsilyl)dibenzo[a,e]pentalene
_chemical_name_common            ?
_chemical_melting_point          431--433
_chemical_formula_moiety         'C25 H32 Si2'
_chemical_formula_sum            'C25 H32 Si2'
_chemical_formula_weight         388.68

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'
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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.657(2)
_cell_length_b                   34.537(13)
_cell_length_c                   19.811(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4555(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    93
_cell_measurement_reflns_used    10330
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      31.1

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_F_000             1680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.163
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            27767
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_av_R_equivalents  0.1158
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.564
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4210
_reflns_number_gt                3758
_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       'RIGAKU CrystalClear'
_computing_cell_refinement       'RIGAKU CrystalClear'
_computing_data_reduction        'RIGAKU CrystalClear'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto, et al.)'
_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)+(0.0846P)²+6.9507P] 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         4210
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1140
_refine_ls_R_factor_gt           0.0987
_refine_ls_wR_factor_ref         0.2401
_refine_ls_wR_factor_gt          0.2249
_refine_ls_goodness_of_fit_ref   1.318
_refine_ls_restrained_S_all      1.318
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

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 0.12120(17) 0.41382(3) 0.41236(6) 0.0196(3) Uani 1 1 d . . . . .
Si2 Si 0.80961(19) 0.30308(4) 0.60452(7) 0.0256(4) Uani 1 1 d . . . . .
C15 C 0.4114(6) 0.39683(13) 0.5739(2) 0.0219(9) Uani 1 1 d . . . . .
C7 C 0.5812(7) 0.33052(12) 0.4427(2) 0.0231(10) Uani 1 1 d . . . . .
C13 C 0.3383(7) 0.43880(13) 0.6674(2) 0.0248(10) Uani 1 1 d . . . . .
H7 H 0.2707 0.4599 0.6856 0.030 Uiso 1 1 calc R U . . .
C3 C 0.4300(7) 0.34254(12) 0.3334(2) 0.0240(10) Uani 1 1 d . . . . .
H1 H 0.3406 0.3560 0.3060 0.029 Uiso 1 1 calc R U . . .
C8 C 0.5645(6) 0.34774(12) 0.5113(2) 0.0210(9) Uani 1 1 d . . . . .
C16 C 0.4179(6) 0.37921(12) 0.5052(2) 0.0219(9) Uani 1 1 d . . . . .
C5 C 0.6846(7) 0.29288(13) 0.3463(2) 0.0260(10) Uani 1 1 d . . . . .
H3 H 0.7630 0.2733 0.3276 0.031 Uiso 1 1 calc R U . . .
C4 C 0.5519(7) 0.31325(13) 0.3060(2) 0.0248(10) Uani 1 1 d . . . . .
H2 H 0.5431 0.3075 0.2603 0.030 Uiso 1 1 calc R U . . .
C10 C 0.5417(7) 0.37523(13) 0.6153(2) 0.0233(10) Uani 1 1 d . . . . .
C14 C 0.3093(7) 0.42882(13) 0.5996(2) 0.0242(10) Uani 1 1 d . . . . .
H8 H 0.2237 0.4432 0.5723 0.029 Uiso 1 1 calc R U . . .
C1 C 0.3351(7) 0.38188(12) 0.4430(2) 0.0231(10) Uani 1 1 d . . . . .
C17 C 0.2311(7) 0.46154(13) 0.3816(2) 0.0241(10) Uani 1 1 d . . . . .
C2 C 0.4440(7) 0.35120(13) 0.4018(2) 0.0239(10) Uani 1 1 d . . . . .
C18 C 0.3423(7) 0.48217(13) 0.4397(2) 0.0292(11) Uani 1 1 d . . . . .
H9 H 0.3979 0.5061 0.4235 0.044 Uiso 1 1 calc R U . . .
H10 H 0.4485 0.4658 0.4560 0.044 Uiso 1 1 calc R U . . .
H11 H 0.2498 0.4874 0.4757 0.044 Uiso 1 1 calc R U . . .
C6 C 0.7015(7) 0.30167(13) 0.4155(2) 0.0267(10) Uani 1 1 d . . . . .
H4 H 0.7921 0.2883 0.4426 0.032 Uiso 1 1 calc R U . . .
C12 C 0.4663(7) 0.41750(13) 0.7071(2) 0.0291(11) Uani 1 1 d . . . . .
H6 H 0.4852 0.4247 0.7518 0.035 Uiso 1 1 calc R U . . .
C11 C 0.5690(7) 0.38517(13) 0.6819(2) 0.0282(11) Uani 1 1 d . . . . .
H5 H 0.6536 0.3708 0.7096 0.034 Uiso 1 1 calc R U . . .
C9 C 0.6350(7) 0.34280(13) 0.5751(2) 0.0250(10) Uani 1 1 d . . . . .
C20 C 0.3798(8) 0.45432(14) 0.3242(2) 0.0362(13) Uani 1 1 d . . . . .
H15 H 0.4325 0.4786 0.3086 0.054 Uiso 1 1 calc R U . . .
H16 H 0.3124 0.4415 0.2877 0.054 Uiso 1 1 calc R U . . .
H17 H 0.4879 0.4384 0.3402 0.054 Uiso 1 1 calc R U . . .
C22 C -0.0169(7) 0.38952(13) 0.3419(2) 0.0285(11) Uani 1 1 d . . . . .
H21 H -0.0315 0.3625 0.3518 0.043 Uiso 1 1 calc R U . . .
H22 H 0.0572 0.3926 0.3007 0.043 Uiso 1 1 calc R U . . .
H23 H -0.1473 0.4011 0.3370 0.043 Uiso 1 1 calc R U . . .
C19 C 0.0592(8) 0.48781(13) 0.3575(3) 0.0351(12) Uani 1 1 d . . . . .
H12 H -0.0398 0.4900 0.3926 0.053 Uiso 1 1 calc R U . . .
H13 H -0.0013 0.4768 0.3180 0.053 Uiso 1 1 calc R U . . .
H14 H 0.1114 0.5130 0.3471 0.053 Uiso 1 1 calc R U . . .
C21 C -0.0697(7) 0.42187(14) 0.4809(2) 0.0298(11) Uani 1 1 d . . . . .
H18 H -0.2020 0.4220 0.4616 0.045 Uiso 1 1 calc R U . . .
H19 H -0.0446 0.4463 0.5025 0.045 Uiso 1 1 calc R U . . .
H20 H -0.0601 0.4014 0.5136 0.045 Uiso 1 1 calc R U . . .
C24 C 0.6950(8) 0.25596(14) 0.5799(3) 0.0368(13) Uani 1 1 d . . . . .
H27 H 0.6539 0.2571 0.5335 0.055 Uiso 1 1 calc R U . . .
H28 H 0.5803 0.2509 0.6079 0.055 Uiso 1 1 calc R U . . .
H29 H 0.7919 0.2356 0.5856 0.055 Uiso 1 1 calc R U . . .
C23 C 1.0650(7) 0.31128(14) 0.5687(3) 0.0354(12) Uani 1 1 d . . . . .
H24 H 1.0551 0.3147 0.5208 0.053 Uiso 1 1 calc R U . . .
H25 H 1.1486 0.2893 0.5783 0.053 Uiso 1 1 calc R U . . .
H26 H 1.1227 0.3340 0.5887 0.053 Uiso 1 1 calc R U . . .
C25 C 0.8347(9) 0.30128(16) 0.6986(3) 0.0453(14) Uani 1 1 d . . . . .
H30 H 0.9088 0.2786 0.7113 0.068 Uiso 1 1 calc R U . . .
H31 H 0.7035 0.3004 0.7187 0.068 Uiso 1 1 calc R U . . .
H32 H 0.9045 0.3239 0.7141 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
Si1 C22 1.870(4) . ?
Si1 C21 1.881(5) . ?
Si1 C1 1.900(5) . ?
Si1 C17 1.903(5) . ?
Si2 C24 1.862(5) . ?
Si2 C23 1.863(5) . ?
Si2 C25 1.873(5) . ?
Si2 C9 1.890(5) . ?
C15 C14 1.394(6) . ?
C15 C10 1.408(6) . ?
C15 C16 1.490(6) . ?
C7 C6 1.387(6) . ?
C7 C2 1.414(6) . ?
C7 C8 1.487(6) . ?
C13 C12 1.373(6) . ?
C13 C14 1.400(6) . ?
C13 H7 0.9300 . ?
C3 C2 1.391(6) . ?
C3 C4 1.406(6) . ?
C3 H1 0.9300 . ?
C8 C9 1.360(6) . ?
C8 C16 1.466(6) . ?
C16 C1 1.354(6) . ?
C5 C4 1.383(6) . ?
C5 C6 1.409(6) . ?
C5 H3 0.9300 . ?
C4 H2 0.9300 . ?
C10 C11 1.375(6) . ?
C10 C9 1.508(6) . ?
C14 H8 0.9300 . ?
C1 C2 1.521(6) . ?
C17 C20 1.529(6) . ?
C17 C19 1.536(6) . ?
C17 C18 1.543(6) . ?
C18 H9 0.9600 . ?
C18 H10 0.9600 . ?
C18 H11 0.9600 . ?
C6 H4 0.9300 . ?
C12 C11 1.401(6) . ?
C12 H6 0.9300 . ?
C11 H5 0.9300 . ?
C20 H15 0.9600 . ?
C20 H16 0.9600 . ?
C20 H17 0.9600 . ?
C22 H21 0.9600 . ?
C22 H22 0.9600 . ?
C22 H23 0.9600 . ?
C19 H12 0.9600 . ?
C19 H13 0.9600 . ?
C19 H14 0.9600 . ?
C21 H18 0.9600 . ?
C21 H19 0.9600 . ?
C21 H20 0.9600 . ?
C24 H27 0.9600 . ?
C24 H28 0.9600 . ?
C24 H29 0.9600 . ?
C23 H24 0.9600 . ?
C23 H25 0.9600 . ?
C23 H26 0.9600 . ?
C25 H30 0.9600 . ?
C25 H31 0.9600 . ?
C25 H32 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 Si1 C21 105.9(2) . . ?
C22 Si1 C1 110.2(2) . . ?
C21 Si1 C1 111.2(2) . . ?
C22 Si1 C17 109.8(2) . . ?
C21 Si1 C17 111.3(2) . . ?
C1 Si1 C17 108.5(2) . . ?
C24 Si2 C23 114.0(2) . . ?
C24 Si2 C25 105.6(3) . . ?
C23 Si2 C25 107.6(3) . . ?
C24 Si2 C9 107.6(2) . . ?
C23 Si2 C9 109.5(2) . . ?
C25 Si2 C9 112.7(2) . . ?
C14 C15 C10 120.5(4) . . ?
C14 C15 C16 132.2(4) . . ?
C10 C15 C16 107.3(4) . . ?
C6 C7 C2 120.9(4) . . ?
C6 C7 C8 133.3(4) . . ?
C2 C7 C8 105.8(4) . . ?
C12 C13 C14 120.2(4) . . ?
C12 C13 H7 119.9 . . ?
C14 C13 H7 119.9 . . ?
C2 C3 C4 119.5(4) . . ?
C2 C3 H1 120.3 . . ?
C4 C3 H1 120.3 . . ?
C9 C8 C16 113.5(4) . . ?
C9 C8 C7 140.7(4) . . ?
C16 C8 C7 105.8(4) . . ?
C1 C16 C8 113.3(4) . . ?
C1 C16 C15 142.3(4) . . ?
C8 C16 C15 104.3(4) . . ?
C4 C5 C6 120.2(4) . . ?
C4 C5 H3 119.9 . . ?
C6 C5 H3 119.9 . . ?
C5 C4 C3 120.8(4) . . ?
C5 C4 H2 119.6 . . ?
C3 C4 H2 119.6 . . ?
C11 C10 C15 120.6(4) . . ?
C11 C10 C9 129.6(4) . . ?
C15 C10 C9 109.8(4) . . ?
C15 C14 C13 118.6(4) . . ?
C15 C14 H8 120.7 . . ?
C13 C14 H8 120.7 . . ?
C16 C1 C2 104.3(4) . . ?
C16 C1 Si1 129.4(3) . . ?
C2 C1 Si1 126.2(3) . . ?
C20 C17 C19 110.3(4) . . ?
C20 C17 C18 108.6(4) . . ?
C19 C17 C18 108.4(4) . . ?
C20 C17 Si1 110.2(3) . . ?
C19 C17 Si1 109.0(3) . . ?
C18 C17 Si1 110.2(3) . . ?
C3 C2 C7 119.5(4) . . ?
C3 C2 C1 129.8(4) . . ?
C7 C2 C1 110.7(4) . . ?
C17 C18 H9 109.5 . . ?
C17 C18 H10 109.5 . . ?
H9 C18 H10 109.5 . . ?
C17 C18 H11 109.5 . . ?
H9 C18 H11 109.5 . . ?
H10 C18 H11 109.5 . . ?
C7 C6 C5 119.1(4) . . ?
C7 C6 H4 120.4 . . ?
C5 C6 H4 120.4 . . ?
C13 C12 C11 121.7(4) . . ?
C13 C12 H6 119.1 . . ?
C11 C12 H6 119.1 . . ?
C10 C11 C12 118.4(4) . . ?
C10 C11 H5 120.8 . . ?
C12 C11 H5 120.8 . . ?
C8 C9 C10 104.8(4) . . ?
C8 C9 Si2 126.2(3) . . ?
C10 C9 Si2 129.0(3) . . ?
C17 C20 H15 109.5 . . ?
C17 C20 H16 109.5 . . ?
H15 C20 H16 109.5 . . ?
C17 C20 H17 109.5 . . ?
H15 C20 H17 109.5 . . ?
H16 C20 H17 109.5 . . ?
Si1 C22 H21 109.5 . . ?
Si1 C22 H22 109.5 . . ?
H21 C22 H22 109.5 . . ?
Si1 C22 H23 109.5 . . ?
H21 C22 H23 109.5 . . ?
H22 C22 H23 109.5 . . ?
C17 C19 H12 109.5 . . ?
C17 C19 H13 109.5 . . ?
H12 C19 H13 109.5 . . ?
C17 C19 H14 109.5 . . ?
H12 C19 H14 109.5 . . ?
H13 C19 H14 109.5 . . ?
Si1 C21 H18 109.5 . . ?
Si1 C21 H19 109.5 . . ?
H18 C21 H19 109.5 . . ?
Si1 C21 H20 109.5 . . ?
H18 C21 H20 109.5 . . ?
H19 C21 H20 109.5 . . ?
Si2 C24 H27 109.5 . . ?
Si2 C24 H28 109.5 . . ?
H27 C24 H28 109.5 . . ?
Si2 C24 H29 109.5 . . ?
H27 C24 H29 109.5 . . ?
H28 C24 H29 109.5 . . ?
Si2 C23 H24 109.5 . . ?
Si2 C23 H25 109.5 . . ?
H24 C23 H25 109.5 . . ?
Si2 C23 H26 109.5 . . ?
H24 C23 H26 109.5 . . ?
H25 C23 H26 109.5 . . ?
Si2 C25 H30 109.5 . . ?
Si2 C25 H31 109.5 . . ?
H30 C25 H31 109.5 . . ?
Si2 C25 H32 109.5 . . ?
H30 C25 H32 109.5 . . ?
H31 C25 H32 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 C7 C8 C9 -6.7(9) . . . . ?
C2 C7 C8 C9 175.7(6) . . . . ?
C6 C7 C8 C16 175.9(5) . . . . ?
C2 C7 C8 C16 -1.7(4) . . . . ?
C9 C8 C16 C1 -174.6(4) . . . . ?
C7 C8 C16 C1 3.6(5) . . . . ?
C9 C8 C16 C15 4.1(5) . . . . ?
C7 C8 C16 C15 -177.6(3) . . . . ?
C14 C15 C16 C1 -5.5(10) . . . . ?
C10 C15 C16 C1 176.1(6) . . . . ?
C14 C15 C16 C8 176.4(5) . . . . ?
C10 C15 C16 C8 -2.0(5) . . . . ?
C6 C5 C4 C3 -0.9(7) . . . . ?
C2 C3 C4 C5 0.3(7) . . . . ?
C14 C15 C10 C11 0.5(7) . . . . ?
C16 C15 C10 C11 179.1(4) . . . . ?
C14 C15 C10 C9 -179.1(4) . . . . ?
C16 C15 C10 C9 -0.5(5) . . . . ?
C10 C15 C14 C13 -0.3(6) . . . . ?
C16 C15 C14 C13 -178.5(4) . . . . ?
C12 C13 C14 C15 0.5(7) . . . . ?
C8 C16 C1 C2 -3.7(5) . . . . ?
C15 C16 C1 C2 178.3(5) . . . . ?
C8 C16 C1 Si1 172.9(3) . . . . ?
C15 C16 C1 Si1 -5.1(9) . . . . ?
C4 C3 C2 C7 0.3(6) . . . . ?
C4 C3 C2 C1 178.1(4) . . . . ?
C6 C7 C2 C3 -0.2(6) . . . . ?
C8 C7 C2 C3 177.8(4) . . . . ?
C6 C7 C2 C1 -178.4(4) . . . . ?
C8 C7 C2 C1 -0.4(5) . . . . ?
C16 C1 C2 C3 -175.4(4) . . . . ?
Si1 C1 C2 C3 7.8(7) . . . . ?
C16 C1 C2 C7 2.5(5) . . . . ?
Si1 C1 C2 C7 -174.3(3) . . . . ?
C2 C7 C6 C5 -0.4(6) . . . . ?
C8 C7 C6 C5 -177.8(4) . . . . ?
C4 C5 C6 C7 1.0(7) . . . . ?
C14 C13 C12 C11 -0.9(7) . . . . ?
C15 C10 C11 C12 -0.8(7) . . . . ?
C9 C10 C11 C12 178.7(4) . . . . ?
C13 C12 C11 C10 1.0(7) . . . . ?
C16 C8 C9 C10 -4.4(5) . . . . ?
C7 C8 C9 C10 178.3(5) . . . . ?
C16 C8 C9 Si2 175.0(3) . . . . ?
C7 C8 C9 Si2 -2.3(8) . . . . ?
C11 C10 C9 C8 -176.6(5) . . . . ?
C15 C10 C9 C8 3.0(5) . . . . ?
C11 C10 C9 Si2 4.1(7) . . . . ?
C15 C10 C9 Si2 -176.4(3) . . . . ?
C24 Si2 C9 C8 -53.9(5) . . . . ?
C23 Si2 C9 C8 70.5(5) . . . . ?
C25 Si2 C9 C8 -169.8(4) . . . . ?
C24 Si2 C9 C10 125.4(4) . . . . ?
C23 Si2 C9 C10 -110.3(4) . . . . ?
C25 Si2 C9 C10 9.4(5) . . . . ?

_refine_diff_density_max         0.457
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.169

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/methanol'
####################################################################### 
# 
# 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_PhNpPen
_database_code_depnum_ccdc_archive 'CCDC 1511837'
_audit_update_record             
;
2016-10-27 deposited with the CCDC.
2016-11-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
5-(tert-Butyldimethylsilyl)-12-(trimethylsilyl)benzo[a]naphtho[2,3-e]pentalene
_chemical_name_common            ?
_chemical_melting_point          445--447
_chemical_formula_moiety         'C29 H34 Si2'
_chemical_formula_sum            'C29 H34 Si2'
_chemical_formula_weight         438.74

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'
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                   15.291(8)
_cell_length_b                   11.701(6)
_cell_length_c                   14.170(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.057(7)
_cell_angle_gamma                90
_cell_volume                     2532(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    93
_cell_measurement_reflns_used    7866
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      30.9

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.154
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.336
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            17515
_diffrn_reflns_av_unetI/netI     0.0797
_diffrn_reflns_av_R_equivalents  0.0924
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.259
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4952
_reflns_number_gt                4312
_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       'RIGAKU CrystalClear'
_computing_cell_refinement       'RIGAKU CrystalClear'
_computing_data_reduction        'RIGAKU CrystalClear'
_computing_structure_solution    'SHELXLT-2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto, et al.)'
_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)+(0.1001P)²+3.0719P] 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         4952
_refine_ls_number_parameters     288
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0772
_refine_ls_wR_factor_ref         0.2171
_refine_ls_wR_factor_gt          0.1967
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_restrained_S_all      1.168
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001

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 0.34857(6) 0.84195(7) 0.12178(6) 0.0127(2) Uani 1 1 d . . . . .
Si2 Si 0.13159(6) 0.34556(7) 0.27720(6) 0.0157(3) Uani 1 1 d . . . . .
C20 C 0.2321(2) 0.7531(3) 0.2685(2) 0.0137(6) Uani 1 1 d . . . . .
C19 C 0.2172(2) 0.8532(3) 0.3147(2) 0.0165(7) Uani 1 1 d . . . . .
H10 H 0.2411 0.9208 0.2931 0.020 Uiso 1 1 calc R U . . .
C1 C 0.2877(2) 0.7283(3) 0.1871(2) 0.0140(6) Uani 1 1 d . . . . .
C21 C 0.4548(2) 0.8751(3) 0.1920(2) 0.0156(7) Uani 1 1 d . . . . .
C9 C 0.2146(2) 0.4419(3) 0.2238(2) 0.0147(6) Uani 1 1 d . . . . .
C10 C 0.2242(2) 0.5567(3) 0.2401(2) 0.0135(6) Uani 1 1 d . . . . .
C4 C 0.3740(2) 0.5147(3) 0.0452(2) 0.0182(7) Uani 1 1 d . . . . .
H1 H 0.4008 0.5812 0.0255 0.022 Uiso 1 1 calc R U . . .
C12 C 0.1433(2) 0.6476(3) 0.3784(2) 0.0173(7) Uani 1 1 d . . . . .
H5 H 0.1191 0.5795 0.3987 0.021 Uiso 1 1 calc R U . . .
C7 C 0.2944(2) 0.3123(3) 0.1050(2) 0.0174(7) Uani 1 1 d . . . . .
H4 H 0.2683 0.2452 0.1245 0.021 Uiso 1 1 calc R U . . .
C26 C 0.3723(2) 0.8004(3) -0.0021(2) 0.0182(7) Uani 1 1 d . . . . .
H23 H 0.3253 0.7541 -0.0286 0.027 Uiso 1 1 calc R U . . .
H24 H 0.4260 0.7579 -0.0014 0.027 Uiso 1 1 calc R U . . .
H25 H 0.3778 0.8680 -0.0397 0.027 Uiso 1 1 calc R U . . .
C2 C 0.2836(2) 0.6108(3) 0.1751(2) 0.0136(6) Uani 1 1 d . . . . .
C5 C 0.3922(2) 0.4092(3) 0.0028(2) 0.0191(7) Uani 1 1 d . . . . .
H2 H 0.4304 0.4063 -0.0461 0.023 Uiso 1 1 calc R U . . .
C6 C 0.3537(2) 0.3097(3) 0.0333(2) 0.0192(7) Uani 1 1 d . . . . .
H3 H 0.3675 0.2403 0.0058 0.023 Uiso 1 1 calc R U . . .
C17 C 0.1502(2) 0.9577(3) 0.4452(2) 0.0193(7) Uani 1 1 d . . . . .
H9 H 0.1734 1.0261 0.4243 0.023 Uiso 1 1 calc R U . . .
C14 C 0.0787(2) 0.7546(3) 0.5099(2) 0.0213(7) Uani 1 1 d . . . . .
H6 H 0.0547 0.6875 0.5323 0.026 Uiso 1 1 calc R U . . .
C28 C 0.0215(2) 0.4154(3) 0.2645(3) 0.0233(8) Uani 1 1 d . . . . .
H29 H 0.0055 0.4265 0.1987 0.035 Uiso 1 1 calc R U . . .
H30 H 0.0236 0.4880 0.2961 0.035 Uiso 1 1 calc R U . . .
H31 H -0.0212 0.3675 0.2922 0.035 Uiso 1 1 calc R U . . .
C22 C 0.4382(2) 0.9268(3) 0.2890(2) 0.0260(8) Uani 1 1 d . . . . .
H11 H 0.4931 0.9384 0.3238 0.039 Uiso 1 1 calc R U . . .
H12 H 0.4025 0.8756 0.3233 0.039 Uiso 1 1 calc R U . . .
H13 H 0.4086 0.9987 0.2806 0.039 Uiso 1 1 calc R U . . .
C25 C 0.2783(2) 0.9726(3) 0.1091(3) 0.0237(8) Uani 1 1 d . . . . .
H20 H 0.2983 1.0194 0.0590 0.036 Uiso 1 1 calc R U . . .
H21 H 0.2818 1.0149 0.1672 0.036 Uiso 1 1 calc R U . . .
H22 H 0.2187 0.9503 0.0946 0.036 Uiso 1 1 calc R U . . .
C16 C 0.1017(2) 0.9572(3) 0.5237(2) 0.0209(7) Uani 1 1 d . . . . .
H8 H 0.0925 1.0253 0.5556 0.025 Uiso 1 1 calc R U . . .
C15 C 0.0658(2) 0.8557(3) 0.5566(3) 0.0231(8) Uani 1 1 d . . . . .
H7 H 0.0332 0.8566 0.6102 0.028 Uiso 1 1 calc R U . . .
C23 C 0.5091(2) 0.9595(3) 0.1362(2) 0.0249(8) Uani 1 1 d . . . . .
H14 H 0.4771 1.0296 0.1270 0.037 Uiso 1 1 calc R U . . .
H15 H 0.5205 0.9270 0.0759 0.037 Uiso 1 1 calc R U . . .
H16 H 0.5635 0.9746 0.1708 0.037 Uiso 1 1 calc R U . . .
C24 C 0.5080(2) 0.7640(3) 0.2081(3) 0.0273(8) Uani 1 1 d . . . . .
H17 H 0.5612 0.7806 0.2446 0.041 Uiso 1 1 calc R U . . .
H18 H 0.5220 0.7325 0.1481 0.041 Uiso 1 1 calc R U . . .
H19 H 0.4740 0.7098 0.2414 0.041 Uiso 1 1 calc R U . . .
C27 C 0.1632(3) 0.3189(3) 0.4046(3) 0.0294(9) Uani 1 1 d . . . . .
H26 H 0.1170 0.2783 0.4333 0.044 Uiso 1 1 calc R U . . .
H27 H 0.1730 0.3906 0.4364 0.044 Uiso 1 1 calc R U . . .
H28 H 0.2159 0.2742 0.4095 0.044 Uiso 1 1 calc R U . . .
C29 C 0.1203(3) 0.2049(3) 0.2150(3) 0.0409(11) Uani 1 1 d . . . . .
H32 H 0.0715 0.1638 0.2381 0.061 Uiso 1 1 calc R U . . .
H33 H 0.1729 0.1611 0.2266 0.061 Uiso 1 1 calc R U . . .
H34 H 0.1108 0.2176 0.1483 0.061 Uiso 1 1 calc R U . . .
C18 C 0.1654(2) 0.8553(3) 0.3955(2) 0.0154(7) Uani 1 1 d . . . . .
C3 C 0.3160(2) 0.5184(3) 0.1163(2) 0.0141(6) Uani 1 1 d . . . . .
C8 C 0.2745(2) 0.4160(3) 0.1470(2) 0.0141(6) Uani 1 1 d . . . . .
C11 C 0.1932(2) 0.6479(3) 0.3013(2) 0.0145(7) Uani 1 1 d . . . . .
C13 C 0.1281(2) 0.7514(3) 0.4281(2) 0.0172(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si1 C25 1.871(4) . ?
Si1 C26 1.876(3) . ?
Si1 C1 1.893(3) . ?
Si1 C21 1.899(3) . ?
Si2 C27 1.870(4) . ?
Si2 C29 1.871(4) . ?
Si2 C28 1.871(4) . ?
Si2 C9 1.886(3) . ?
C20 C19 1.366(5) . ?
C20 C11 1.453(4) . ?
C20 C1 1.498(4) . ?
C19 C18 1.427(5) . ?
C19 H10 0.9300 . ?
C1 C2 1.386(5) . ?
C21 C23 1.536(4) . ?
C21 C22 1.536(4) . ?
C21 C24 1.544(5) . ?
C9 C10 1.369(5) . ?
C9 C8 1.491(4) . ?
C10 C11 1.470(4) . ?
C10 C2 1.471(4) . ?
C4 C3 1.378(4) . ?
C4 C5 1.408(5) . ?
C4 H1 0.9300 . ?
C12 C11 1.366(5) . ?
C12 C13 1.429(5) . ?
C12 H5 0.9300 . ?
C7 C8 1.392(5) . ?
C7 C6 1.398(5) . ?
C7 H4 0.9300 . ?
C26 H23 0.9600 . ?
C26 H24 0.9600 . ?
C26 H25 0.9600 . ?
C2 C3 1.467(4) . ?
C5 C6 1.384(5) . ?
C5 H2 0.9300 . ?
C6 H3 0.9300 . ?
C17 C16 1.370(5) . ?
C17 C18 1.416(5) . ?
C17 H9 0.9300 . ?
C14 C15 1.375(5) . ?
C14 C13 1.418(5) . ?
C14 H6 0.9300 . ?
C28 H29 0.9600 . ?
C28 H30 0.9600 . ?
C28 H31 0.9600 . ?
C22 H11 0.9600 . ?
C22 H12 0.9600 . ?
C22 H13 0.9600 . ?
C25 H20 0.9600 . ?
C25 H21 0.9600 . ?
C25 H22 0.9600 . ?
C16 C15 1.399(5) . ?
C16 H8 0.9300 . ?
C15 H7 0.9300 . ?
C23 H14 0.9600 . ?
C23 H15 0.9600 . ?
C23 H16 0.9600 . ?
C24 H17 0.9600 . ?
C24 H18 0.9600 . ?
C24 H19 0.9600 . ?
C27 H26 0.9600 . ?
C27 H27 0.9600 . ?
C27 H28 0.9600 . ?
C29 H32 0.9600 . ?
C29 H33 0.9600 . ?
C29 H34 0.9600 . ?
C18 C13 1.430(5) . ?
C3 C8 1.434(4) . ?

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
C25 Si1 C26 105.10(16) . . ?
C25 Si1 C1 109.01(15) . . ?
C26 Si1 C1 113.59(15) . . ?
C25 Si1 C21 110.76(16) . . ?
C26 Si1 C21 109.89(15) . . ?
C1 Si1 C21 108.47(14) . . ?
C27 Si2 C29 108.7(2) . . ?
C27 Si2 C28 110.51(17) . . ?
C29 Si2 C28 106.2(2) . . ?
C27 Si2 C9 110.01(16) . . ?
C29 Si2 C9 112.58(17) . . ?
C28 Si2 C9 108.76(15) . . ?
C19 C20 C11 119.4(3) . . ?
C19 C20 C1 130.6(3) . . ?
C11 C20 C1 109.9(3) . . ?
C20 C19 C18 120.8(3) . . ?
C20 C19 H10 119.6 . . ?
C18 C19 H10 119.6 . . ?
C2 C1 C20 105.3(3) . . ?
C2 C1 Si1 131.1(2) . . ?
C20 C1 Si1 123.7(2) . . ?
C23 C21 C22 109.1(3) . . ?
C23 C21 C24 108.8(3) . . ?
C22 C21 C24 108.1(3) . . ?
C23 C21 Si1 109.4(2) . . ?
C22 C21 Si1 111.8(2) . . ?
C24 C21 Si1 109.5(2) . . ?
C10 C9 C8 105.0(3) . . ?
C10 C9 Si2 126.0(2) . . ?
C8 C9 Si2 128.6(2) . . ?
C9 C10 C11 141.0(3) . . ?
C9 C10 C2 112.4(3) . . ?
C11 C10 C2 106.7(3) . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H1 120.3 . . ?
C5 C4 H1 120.3 . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H5 119.9 . . ?
C13 C12 H5 119.9 . . ?
C8 C7 C6 119.6(3) . . ?
C8 C7 H4 120.2 . . ?
C6 C7 H4 120.2 . . ?
Si1 C26 H23 109.5 . . ?
Si1 C26 H24 109.5 . . ?
H23 C26 H24 109.5 . . ?
Si1 C26 H25 109.5 . . ?
H23 C26 H25 109.5 . . ?
H24 C26 H25 109.5 . . ?
C1 C2 C3 141.9(3) . . ?
C1 C2 C10 112.0(3) . . ?
C3 C2 C10 106.0(3) . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H2 119.8 . . ?
C4 C5 H2 119.8 . . ?
C5 C6 C7 120.8(3) . . ?
C5 C6 H3 119.6 . . ?
C7 C6 H3 119.6 . . ?
C16 C17 C18 120.7(3) . . ?
C16 C17 H9 119.6 . . ?
C18 C17 H9 119.6 . . ?
C15 C14 C13 120.8(3) . . ?
C15 C14 H6 119.6 . . ?
C13 C14 H6 119.6 . . ?
Si2 C28 H29 109.5 . . ?
Si2 C28 H30 109.5 . . ?
H29 C28 H30 109.5 . . ?
Si2 C28 H31 109.5 . . ?
H29 C28 H31 109.5 . . ?
H30 C28 H31 109.5 . . ?
C21 C22 H11 109.5 . . ?
C21 C22 H12 109.5 . . ?
H11 C22 H12 109.5 . . ?
C21 C22 H13 109.5 . . ?
H11 C22 H13 109.5 . . ?
H12 C22 H13 109.5 . . ?
Si1 C25 H20 109.5 . . ?
Si1 C25 H21 109.5 . . ?
H20 C25 H21 109.5 . . ?
Si1 C25 H22 109.5 . . ?
H20 C25 H22 109.5 . . ?
H21 C25 H22 109.5 . . ?
C17 C16 C15 120.9(3) . . ?
C17 C16 H8 119.6 . . ?
C15 C16 H8 119.5 . . ?
C14 C15 C16 120.1(3) . . ?
C14 C15 H7 120.0 . . ?
C16 C15 H7 120.0 . . ?
C21 C23 H14 109.5 . . ?
C21 C23 H15 109.5 . . ?
H14 C23 H15 109.5 . . ?
C21 C23 H16 109.5 . . ?
H14 C23 H16 109.5 . . ?
H15 C23 H16 109.5 . . ?
C21 C24 H17 109.5 . . ?
C21 C24 H18 109.5 . . ?
H17 C24 H18 109.5 . . ?
C21 C24 H19 109.5 . . ?
H17 C24 H19 109.5 . . ?
H18 C24 H19 109.5 . . ?
Si2 C27 H26 109.5 . . ?
Si2 C27 H27 109.5 . . ?
H26 C27 H27 109.5 . . ?
Si2 C27 H28 109.5 . . ?
H26 C27 H28 109.5 . . ?
H27 C27 H28 109.5 . . ?
Si2 C29 H32 109.5 . . ?
Si2 C29 H33 109.5 . . ?
H32 C29 H33 109.5 . . ?
Si2 C29 H34 109.5 . . ?
H32 C29 H34 109.5 . . ?
H33 C29 H34 109.5 . . ?
C17 C18 C19 121.8(3) . . ?
C17 C18 C13 118.7(3) . . ?
C19 C18 C13 119.5(3) . . ?
C4 C3 C8 120.5(3) . . ?
C4 C3 C2 133.5(3) . . ?
C8 C3 C2 106.0(3) . . ?
C7 C8 C3 119.3(3) . . ?
C7 C8 C9 130.3(3) . . ?
C3 C8 C9 110.5(3) . . ?
C12 C11 C20 120.9(3) . . ?
C12 C11 C10 133.0(3) . . ?
C20 C11 C10 106.0(3) . . ?
C14 C13 C12 122.2(3) . . ?
C14 C13 C18 118.8(3) . . ?
C12 C13 C18 119.0(3) . . ?

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
C11 C20 C19 C18 1.2(5) . . . . ?
C1 C20 C19 C18 -175.9(3) . . . . ?
C19 C20 C1 C2 175.2(3) . . . . ?
C11 C20 C1 C2 -2.0(3) . . . . ?
C19 C20 C1 Si1 -3.9(5) . . . . ?
C11 C20 C1 Si1 178.8(2) . . . . ?
C25 Si1 C1 C2 142.1(3) . . . . ?
C26 Si1 C1 C2 25.3(4) . . . . ?
C21 Si1 C1 C2 -97.2(3) . . . . ?
C25 Si1 C1 C20 -39.0(3) . . . . ?
C26 Si1 C1 C20 -155.8(2) . . . . ?
C21 Si1 C1 C20 81.7(3) . . . . ?
C25 Si1 C21 C23 -65.3(3) . . . . ?
C26 Si1 C21 C23 50.4(3) . . . . ?
C1 Si1 C21 C23 175.1(2) . . . . ?
C25 Si1 C21 C22 55.7(3) . . . . ?
C26 Si1 C21 C22 171.4(2) . . . . ?
C1 Si1 C21 C22 -63.9(3) . . . . ?
C25 Si1 C21 C24 175.5(2) . . . . ?
C26 Si1 C21 C24 -68.8(3) . . . . ?
C1 Si1 C21 C24 55.9(3) . . . . ?
C27 Si2 C9 C10 -73.1(3) . . . . ?
C29 Si2 C9 C10 165.4(3) . . . . ?
C28 Si2 C9 C10 48.0(3) . . . . ?
C27 Si2 C9 C8 115.8(3) . . . . ?
C29 Si2 C9 C8 -5.6(4) . . . . ?
C28 Si2 C9 C8 -123.0(3) . . . . ?
C8 C9 C10 C11 -178.5(4) . . . . ?
Si2 C9 C10 C11 8.7(6) . . . . ?
C8 C9 C10 C2 3.2(4) . . . . ?
Si2 C9 C10 C2 -169.6(2) . . . . ?
C20 C1 C2 C3 -179.8(4) . . . . ?
Si1 C1 C2 C3 -0.7(6) . . . . ?
C20 C1 C2 C10 3.5(3) . . . . ?
Si1 C1 C2 C10 -177.5(2) . . . . ?
C9 C10 C2 C1 175.2(3) . . . . ?
C11 C10 C2 C1 -3.7(4) . . . . ?
C9 C10 C2 C3 -2.7(4) . . . . ?
C11 C10 C2 C3 178.4(2) . . . . ?
C3 C4 C5 C6 -1.3(5) . . . . ?
C4 C5 C6 C7 1.7(5) . . . . ?
C8 C7 C6 C5 -0.8(5) . . . . ?
C18 C17 C16 C15 -0.2(5) . . . . ?
C13 C14 C15 C16 -0.1(5) . . . . ?
C17 C16 C15 C14 -0.2(5) . . . . ?
C16 C17 C18 C19 -178.7(3) . . . . ?
C16 C17 C18 C13 0.9(5) . . . . ?
C20 C19 C18 C17 179.1(3) . . . . ?
C20 C19 C18 C13 -0.5(5) . . . . ?
C5 C4 C3 C8 0.0(5) . . . . ?
C5 C4 C3 C2 179.2(3) . . . . ?
C1 C2 C3 C4 4.8(7) . . . . ?
C10 C2 C3 C4 -178.4(3) . . . . ?
C1 C2 C3 C8 -176.0(4) . . . . ?
C10 C2 C3 C8 0.9(3) . . . . ?
C6 C7 C8 C3 -0.5(5) . . . . ?
C6 C7 C8 C9 -179.9(3) . . . . ?
C4 C3 C8 C7 0.9(5) . . . . ?
C2 C3 C8 C7 -178.5(3) . . . . ?
C4 C3 C8 C9 -179.7(3) . . . . ?
C2 C3 C8 C9 1.0(3) . . . . ?
C10 C9 C8 C7 176.9(3) . . . . ?
Si2 C9 C8 C7 -10.6(5) . . . . ?
C10 C9 C8 C3 -2.6(4) . . . . ?
Si2 C9 C8 C3 169.9(2) . . . . ?
C13 C12 C11 C20 0.3(5) . . . . ?
C13 C12 C11 C10 175.9(3) . . . . ?
C19 C20 C11 C12 -1.1(5) . . . . ?
C1 C20 C11 C12 176.5(3) . . . . ?
C19 C20 C11 C10 -177.8(3) . . . . ?
C1 C20 C11 C10 -0.1(3) . . . . ?
C9 C10 C11 C12 7.7(7) . . . . ?
C2 C10 C11 C12 -173.9(3) . . . . ?
C9 C10 C11 C20 -176.2(4) . . . . ?
C2 C10 C11 C20 2.2(3) . . . . ?
C15 C14 C13 C12 179.5(3) . . . . ?
C15 C14 C13 C18 0.7(5) . . . . ?
C11 C12 C13 C14 -178.3(3) . . . . ?
C11 C12 C13 C18 0.4(5) . . . . ?
C17 C18 C13 C14 -1.1(5) . . . . ?
C19 C18 C13 C14 178.5(3) . . . . ?
C17 C18 C13 C12 -179.9(3) . . . . ?
C19 C18 C13 C12 -0.3(5) . . . . ?

_refine_diff_density_max         0.580
_refine_diff_density_min         -0.603
_refine_diff_density_rms         0.143

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/methanol'
####################################################################### 
# 
# 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_ANPh2Pen
_database_code_depnum_ccdc_archive 'CCDC 1511838'
_audit_update_record             
;
2016-10-27 deposited with the CCDC.
2016-11-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
5-(tert-Butyldimethylsilyl)-3-(dimethylamino)-8-nitro-10-(trimethylsilyl)dibenzo[a,e]pentalene
_chemical_name_common            ?
_chemical_melting_point          457--459
_chemical_formula_moiety         'C27 H36 N2 O2 Si2'
_chemical_formula_sum            'C27 H36 N2 O2 Si2'
_chemical_formula_weight         476.76

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'
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'

_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                   7.221(3)
_cell_length_b                   11.790(5)
_cell_length_c                   16.389(9)
_cell_angle_alpha                110.915(10)
_cell_angle_beta                 93.663(16)
_cell_angle_gamma                94.99(2)
_cell_volume                     1291.6(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    93
_cell_measurement_reflns_used    3326
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      31.0

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.164
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.642
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            9281
_diffrn_reflns_av_unetI/netI     0.1151
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.855
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             4927
_reflns_number_gt                3057
_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       'RIGAKU CrystalClear'
_computing_cell_refinement       'RIGAKU CrystalClear'
_computing_data_reduction        'RIGAKU CrystalClear'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto, et al.)'
_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)+(0.1050P)²+0.7445P] 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         4927
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1298
_refine_ls_R_factor_gt           0.0765
_refine_ls_wR_factor_ref         0.2282
_refine_ls_wR_factor_gt          0.1805
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

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 0.91246(15) 0.55241(10) 0.21593(7) 0.0160(3) Uani 1 1 d . . . . .
Si2 Si 0.62299(15) 0.09742(10) 0.39024(7) 0.0167(3) Uani 1 1 d . . . . .
C12 C 0.7331(5) 0.4674(4) 0.5076(3) 0.0145(9) Uani 1 1 d . . . . .
H4 H 0.6922 0.4074 0.5309 0.017 Uiso 1 1 calc R U . . .
C11 C 0.7594(5) 0.4357(4) 0.4201(3) 0.0135(9) Uani 1 1 d . . . . .
C9 C 0.6959(5) 0.1942(4) 0.3266(3) 0.0160(9) Uani 1 1 d . . . . .
C10 C 0.7384(5) 0.3186(4) 0.3467(3) 0.0136(9) Uani 1 1 d . . . . .
C4 C 0.7845(5) 0.1954(4) 0.1069(3) 0.0158(9) Uani 1 1 d . . . . .
H1 H 0.8143 0.2573 0.0838 0.019 Uiso 1 1 calc R U . . .
C2 C 0.7866(5) 0.3457(4) 0.2694(2) 0.0135(9) Uani 1 1 d . . . . .
C15 C 0.8523(5) 0.6486(4) 0.4410(3) 0.0180(9) Uani 1 1 d . . . . .
H6 H 0.8920 0.7093 0.4183 0.022 Uiso 1 1 calc R U . . .
C16 C 0.8183(5) 0.5269(4) 0.3859(2) 0.0131(8) Uani 1 1 d . . . . .
C8 C 0.7153(5) 0.1365(4) 0.2306(3) 0.0153(9) Uani 1 1 d . . . . .
C13 C 0.7689(5) 0.5912(4) 0.5609(2) 0.0149(9) Uani 1 1 d . . . . .
C1 C 0.8391(5) 0.4688(4) 0.2896(3) 0.0138(8) Uani 1 1 d . . . . .
C5 C 0.7596(5) 0.0694(4) 0.0500(3) 0.0172(9) Uani 1 1 d . . . . .
C3 C 0.7654(5) 0.2268(4) 0.1948(3) 0.0141(9) Uani 1 1 d . . . . .
C6 C 0.7125(6) -0.0184(4) 0.0864(3) 0.0205(10) Uani 1 1 d . . . . .
H2 H 0.6951 -0.1024 0.0496 0.025 Uiso 1 1 calc R U . . .
C14 C 0.8280(5) 0.6818(4) 0.5300(3) 0.0169(9) Uani 1 1 d . . . . .
H5 H 0.8517 0.7648 0.5685 0.020 Uiso 1 1 calc R U . . .
C7 C 0.6904(6) 0.0143(4) 0.1757(3) 0.0187(9) Uani 1 1 d . . . . .
H3 H 0.6583 -0.0472 0.1988 0.022 Uiso 1 1 calc R U . . .
C23 C 1.0673(6) 0.6980(4) 0.2781(3) 0.0208(10) Uani 1 1 d . . . . .
H22 H 0.9937 0.7577 0.3162 0.031 Uiso 1 1 calc R U . . .
H23 H 1.1214 0.7309 0.2366 0.031 Uiso 1 1 calc R U . . .
H24 H 1.1678 0.6818 0.3140 0.031 Uiso 1 1 calc R U . . .
C20 C 0.5756(6) 0.6599(4) 0.2389(3) 0.0238(10) Uani 1 1 d . . . . .
H13 H 0.6532 0.7323 0.2807 0.036 Uiso 1 1 calc R U . . .
H14 H 0.5313 0.6067 0.2697 0.036 Uiso 1 1 calc R U . . .
H15 H 0.4683 0.6854 0.2130 0.036 Uiso 1 1 calc R U . . .
C19 C 0.6927(5) 0.5895(4) 0.1656(3) 0.0180(9) Uani 1 1 d . . . . .
C22 C 0.5752(6) 0.4702(4) 0.1050(3) 0.0233(10) Uani 1 1 d . . . . .
H19 H 0.4634 0.4897 0.0780 0.035 Uiso 1 1 calc R U . . .
H20 H 0.5379 0.4207 0.1395 0.035 Uiso 1 1 calc R U . . .
H21 H 0.6495 0.4242 0.0590 0.035 Uiso 1 1 calc R U . . .
C21 C 0.7467(6) 0.6686(4) 0.1125(3) 0.0240(10) Uani 1 1 d . . . . .
H16 H 0.8197 0.6238 0.0654 0.036 Uiso 1 1 calc R U . . .
H17 H 0.8217 0.7444 0.1511 0.036 Uiso 1 1 calc R U . . .
H18 H 0.6334 0.6884 0.0868 0.036 Uiso 1 1 calc R U . . .
C24 C 1.0516(6) 0.4616(4) 0.1278(3) 0.0223(10) Uani 1 1 d . . . . .
H25 H 1.1195 0.4070 0.1486 0.033 Uiso 1 1 calc R U . . .
H26 H 1.1410 0.5173 0.1133 0.033 Uiso 1 1 calc R U . . .
H27 H 0.9672 0.4129 0.0753 0.033 Uiso 1 1 calc R U . . .
C26 C 0.3950(6) 0.0056(4) 0.3333(3) 0.0238(10) Uani 1 1 d . . . . .
H31 H 0.3338 -0.0279 0.3729 0.036 Uiso 1 1 calc R U . . .
H32 H 0.4182 -0.0616 0.2803 0.036 Uiso 1 1 calc R U . . .
H33 H 0.3140 0.0583 0.3171 0.036 Uiso 1 1 calc R U . . .
C27 C 0.8106(6) -0.0031(4) 0.3903(3) 0.0253(10) Uani 1 1 d . . . . .
H34 H 0.9227 0.0469 0.4265 0.038 Uiso 1 1 calc R U . . .
H35 H 0.8404 -0.0442 0.3301 0.038 Uiso 1 1 calc R U . . .
H36 H 0.7666 -0.0644 0.4145 0.038 Uiso 1 1 calc R U . . .
C25 C 0.5919(6) 0.1818(4) 0.5068(3) 0.0245(10) Uani 1 1 d . . . . .
H28 H 0.7124 0.2248 0.5384 0.037 Uiso 1 1 calc R U . . .
H29 H 0.5438 0.1241 0.5332 0.037 Uiso 1 1 calc R U . . .
H30 H 0.5030 0.2413 0.5104 0.037 Uiso 1 1 calc R U . . .
O1 O 0.7772(4) 0.7350(3) 0.7022(2) 0.0291(8) Uani 1 1 d . . . . .
N2 N 0.7429(5) 0.6260(3) 0.6546(2) 0.0190(8) Uani 1 1 d . . . . .
N1 N 0.7858(5) 0.0379(3) -0.0374(2) 0.0221(8) Uani 1 1 d . . . . .
O2 O 0.6921(4) 0.5450(3) 0.6817(2) 0.0274(8) Uani 1 1 d . . . . .
C18 C 0.7553(6) -0.0887(4) -0.0957(3) 0.0253(11) Uani 1 1 d . . . . .
H10 H 0.8356 -0.1364 -0.0735 0.038 Uiso 1 1 calc R U . . .
H11 H 0.7856 -0.0950 -0.1545 0.038 Uiso 1 1 calc R U . . .
H12 H 0.6241 -0.1205 -0.0986 0.038 Uiso 1 1 calc R U . . .
C17 C 0.8160(6) 0.1312(4) -0.0749(3) 0.0260(11) Uani 1 1 d . . . . .
H7 H 0.7063 0.1757 -0.0699 0.039 Uiso 1 1 calc R U . . .
H8 H 0.8358 0.0927 -0.1369 0.039 Uiso 1 1 calc R U . . .
H9 H 0.9263 0.1882 -0.0432 0.039 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 C23 1.873(4) . ?
Si1 C24 1.874(4) . ?
Si1 C1 1.884(4) . ?
Si1 C19 1.898(4) . ?
Si2 C25 1.851(5) . ?
Si2 C9 1.866(4) . ?
Si2 C27 1.876(5) . ?
Si2 C26 1.878(4) . ?
C12 C11 1.378(5) . ?
C12 C13 1.399(5) . ?
C12 H4 0.9500 . ?
C11 C16 1.426(5) . ?
C11 C10 1.459(5) . ?
C9 C10 1.385(5) . ?
C9 C8 1.496(5) . ?
C10 C2 1.468(6) . ?
C4 C3 1.372(5) . ?
C4 C5 1.432(6) . ?
C4 H1 0.9500 . ?
C2 C1 1.380(5) . ?
C2 C3 1.482(5) . ?
C15 C16 1.386(5) . ?
C15 C14 1.395(6) . ?
C15 H6 0.9500 . ?
C16 C1 1.502(5) . ?
C8 C7 1.388(6) . ?
C8 C3 1.420(6) . ?
C13 C14 1.384(6) . ?
C13 N2 1.470(5) . ?
C5 N1 1.375(5) . ?
C5 C6 1.397(6) . ?
C6 C7 1.398(6) . ?
C6 H2 0.9500 . ?
C14 H5 0.9500 . ?
C7 H3 0.9500 . ?
C23 H22 0.9800 . ?
C23 H23 0.9800 . ?
C23 H24 0.9800 . ?
C20 C19 1.546(6) . ?
C20 H13 0.9800 . ?
C20 H14 0.9800 . ?
C20 H15 0.9800 . ?
C19 C21 1.529(6) . ?
C19 C22 1.540(5) . ?
C22 H19 0.9800 . ?
C22 H20 0.9800 . ?
C22 H21 0.9800 . ?
C21 H16 0.9800 . ?
C21 H17 0.9800 . ?
C21 H18 0.9800 . ?
C24 H25 0.9800 . ?
C24 H26 0.9800 . ?
C24 H27 0.9800 . ?
C26 H31 0.9800 . ?
C26 H32 0.9800 . ?
C26 H33 0.9800 . ?
C27 H34 0.9800 . ?
C27 H35 0.9800 . ?
C27 H36 0.9800 . ?
C25 H28 0.9800 . ?
C25 H29 0.9800 . ?
C25 H30 0.9800 . ?
O1 N2 1.236(4) . ?
N2 O2 1.227(4) . ?
N1 C18 1.445(5) . ?
N1 C17 1.446(6) . ?
C18 H10 0.9800 . ?
C18 H11 0.9800 . ?
C18 H12 0.9800 . ?
C17 H7 0.9800 . ?
C17 H8 0.9800 . ?
C17 H9 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
C23 Si1 C24 105.20(19) . . ?
C23 Si1 C1 111.82(19) . . ?
C24 Si1 C1 112.63(19) . . ?
C23 Si1 C19 109.1(2) . . ?
C24 Si1 C19 110.4(2) . . ?
C1 Si1 C19 107.71(18) . . ?
C25 Si2 C9 115.5(2) . . ?
C25 Si2 C27 106.4(2) . . ?
C9 Si2 C27 107.84(19) . . ?
C25 Si2 C26 108.6(2) . . ?
C9 Si2 C26 106.88(19) . . ?
C27 Si2 C26 111.7(2) . . ?
C11 C12 C13 117.5(4) . . ?
C11 C12 H4 121.3 . . ?
C13 C12 H4 121.3 . . ?
C12 C11 C16 120.6(4) . . ?
C12 C11 C10 132.7(4) . . ?
C16 C11 C10 106.7(3) . . ?
C10 C9 C8 105.1(4) . . ?
C10 C9 Si2 134.6(3) . . ?
C8 C9 Si2 120.2(3) . . ?
C9 C10 C11 142.0(4) . . ?
C9 C10 C2 111.6(4) . . ?
C11 C10 C2 106.4(3) . . ?
C3 C4 C5 120.1(4) . . ?
C3 C4 H1 119.9 . . ?
C5 C4 H1 119.9 . . ?
C1 C2 C10 112.1(3) . . ?
C1 C2 C3 141.4(4) . . ?
C10 C2 C3 106.4(3) . . ?
C16 C15 C14 119.9(4) . . ?
C16 C15 H6 120.0 . . ?
C14 C15 H6 120.0 . . ?
C15 C16 C11 120.0(4) . . ?
C15 C16 C1 129.7(4) . . ?
C11 C16 C1 110.2(3) . . ?
C7 C8 C3 118.9(4) . . ?
C7 C8 C9 130.2(4) . . ?
C3 C8 C9 110.9(3) . . ?
C14 C13 C12 123.3(4) . . ?
C14 C13 N2 118.7(4) . . ?
C12 C13 N2 117.9(4) . . ?
C2 C1 C16 104.6(3) . . ?
C2 C1 Si1 129.6(3) . . ?
C16 C1 Si1 125.7(3) . . ?
N1 C5 C6 121.9(4) . . ?
N1 C5 C4 120.0(4) . . ?
C6 C5 C4 118.0(4) . . ?
C4 C3 C8 121.2(4) . . ?
C4 C3 C2 132.9(4) . . ?
C8 C3 C2 105.9(3) . . ?
C5 C6 C7 121.5(4) . . ?
C5 C6 H2 119.2 . . ?
C7 C6 H2 119.2 . . ?
C13 C14 C15 118.6(4) . . ?
C13 C14 H5 120.7 . . ?
C15 C14 H5 120.7 . . ?
C8 C7 C6 120.2(4) . . ?
C8 C7 H3 119.9 . . ?
C6 C7 H3 119.9 . . ?
Si1 C23 H22 109.5 . . ?
Si1 C23 H23 109.5 . . ?
H22 C23 H23 109.5 . . ?
Si1 C23 H24 109.5 . . ?
H22 C23 H24 109.5 . . ?
H23 C23 H24 109.5 . . ?
C19 C20 H13 109.5 . . ?
C19 C20 H14 109.5 . . ?
H13 C20 H14 109.5 . . ?
C19 C20 H15 109.5 . . ?
H13 C20 H15 109.5 . . ?
H14 C20 H15 109.5 . . ?
C21 C19 C22 109.7(3) . . ?
C21 C19 C20 109.3(4) . . ?
C22 C19 C20 109.0(3) . . ?
C21 C19 Si1 109.4(3) . . ?
C22 C19 Si1 109.7(3) . . ?
C20 C19 Si1 109.8(3) . . ?
C19 C22 H19 109.5 . . ?
C19 C22 H20 109.5 . . ?
H19 C22 H20 109.5 . . ?
C19 C22 H21 109.5 . . ?
H19 C22 H21 109.5 . . ?
H20 C22 H21 109.5 . . ?
C19 C21 H16 109.5 . . ?
C19 C21 H17 109.5 . . ?
H16 C21 H17 109.5 . . ?
C19 C21 H18 109.5 . . ?
H16 C21 H18 109.5 . . ?
H17 C21 H18 109.5 . . ?
Si1 C24 H25 109.5 . . ?
Si1 C24 H26 109.5 . . ?
H25 C24 H26 109.5 . . ?
Si1 C24 H27 109.5 . . ?
H25 C24 H27 109.5 . . ?
H26 C24 H27 109.5 . . ?
Si2 C26 H31 109.5 . . ?
Si2 C26 H32 109.5 . . ?
H31 C26 H32 109.5 . . ?
Si2 C26 H33 109.5 . . ?
H31 C26 H33 109.5 . . ?
H32 C26 H33 109.5 . . ?
Si2 C27 H34 109.5 . . ?
Si2 C27 H35 109.5 . . ?
H34 C27 H35 109.5 . . ?
Si2 C27 H36 109.5 . . ?
H34 C27 H36 109.5 . . ?
H35 C27 H36 109.5 . . ?
Si2 C25 H28 109.5 . . ?
Si2 C25 H29 109.5 . . ?
H28 C25 H29 109.5 . . ?
Si2 C25 H30 109.5 . . ?
H28 C25 H30 109.5 . . ?
H29 C25 H30 109.5 . . ?
O2 N2 O1 123.5(4) . . ?
O2 N2 C13 118.4(3) . . ?
O1 N2 C13 118.1(4) . . ?
C5 N1 C18 120.2(4) . . ?
C5 N1 C17 120.5(4) . . ?
C18 N1 C17 118.6(4) . . ?
N1 C18 H10 109.5 . . ?
N1 C18 H11 109.5 . . ?
H10 C18 H11 109.5 . . ?
N1 C18 H12 109.5 . . ?
H10 C18 H12 109.5 . . ?
H11 C18 H12 109.5 . . ?
N1 C17 H7 109.5 . . ?
N1 C17 H8 109.5 . . ?
H7 C17 H8 109.5 . . ?
N1 C17 H9 109.5 . . ?
H7 C17 H9 109.5 . . ?
H8 C17 H9 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
C13 C12 C11 C16 -0.9(6) . . . . ?
C13 C12 C11 C10 179.4(4) . . . . ?
C25 Si2 C9 C10 2.0(5) . . . . ?
C27 Si2 C9 C10 -116.8(4) . . . . ?
C26 Si2 C9 C10 122.9(4) . . . . ?
C25 Si2 C9 C8 -176.7(3) . . . . ?
C27 Si2 C9 C8 64.5(3) . . . . ?
C26 Si2 C9 C8 -55.7(4) . . . . ?
C8 C9 C10 C11 -177.5(5) . . . . ?
Si2 C9 C10 C11 3.7(8) . . . . ?
C8 C9 C10 C2 -0.6(4) . . . . ?
Si2 C9 C10 C2 -179.4(3) . . . . ?
C12 C11 C10 C9 -3.4(9) . . . . ?
C16 C11 C10 C9 176.8(5) . . . . ?
C12 C11 C10 C2 179.6(4) . . . . ?
C16 C11 C10 C2 -0.1(4) . . . . ?
C9 C10 C2 C1 -176.7(3) . . . . ?
C11 C10 C2 C1 1.3(4) . . . . ?
C9 C10 C2 C3 2.0(4) . . . . ?
C11 C10 C2 C3 180.0(3) . . . . ?
C14 C15 C16 C11 -0.3(6) . . . . ?
C14 C15 C16 C1 -178.2(4) . . . . ?
C12 C11 C16 C15 0.9(6) . . . . ?
C10 C11 C16 C15 -179.3(4) . . . . ?
C12 C11 C16 C1 179.2(3) . . . . ?
C10 C11 C16 C1 -1.0(4) . . . . ?
C10 C9 C8 C7 179.6(4) . . . . ?
Si2 C9 C8 C7 -1.4(6) . . . . ?
C10 C9 C8 C3 -1.0(4) . . . . ?
Si2 C9 C8 C3 178.0(3) . . . . ?
C11 C12 C13 C14 0.2(6) . . . . ?
C11 C12 C13 N2 -179.5(3) . . . . ?
C10 C2 C1 C16 -1.8(4) . . . . ?
C3 C2 C1 C16 -179.8(5) . . . . ?
C10 C2 C1 Si1 -179.6(3) . . . . ?
C3 C2 C1 Si1 2.4(8) . . . . ?
C15 C16 C1 C2 179.8(4) . . . . ?
C11 C16 C1 C2 1.7(4) . . . . ?
C15 C16 C1 Si1 -2.3(6) . . . . ?
C11 C16 C1 Si1 179.6(3) . . . . ?
C23 Si1 C1 C2 -154.1(4) . . . . ?
C24 Si1 C1 C2 -35.9(4) . . . . ?
C19 Si1 C1 C2 86.0(4) . . . . ?
C23 Si1 C1 C16 28.5(4) . . . . ?
C24 Si1 C1 C16 146.7(3) . . . . ?
C19 Si1 C1 C16 -91.3(3) . . . . ?
C3 C4 C5 N1 -177.5(4) . . . . ?
C3 C4 C5 C6 1.1(6) . . . . ?
C5 C4 C3 C8 -2.0(6) . . . . ?
C5 C4 C3 C2 178.2(4) . . . . ?
C7 C8 C3 C4 1.8(6) . . . . ?
C9 C8 C3 C4 -177.7(3) . . . . ?
C7 C8 C3 C2 -178.4(4) . . . . ?
C9 C8 C3 C2 2.2(4) . . . . ?
C1 C2 C3 C4 -4.6(9) . . . . ?
C10 C2 C3 C4 177.4(4) . . . . ?
C1 C2 C3 C8 175.5(5) . . . . ?
C10 C2 C3 C8 -2.5(4) . . . . ?
N1 C5 C6 C7 178.5(4) . . . . ?
C4 C5 C6 C7 -0.1(6) . . . . ?
C12 C13 C14 C15 0.4(6) . . . . ?
N2 C13 C14 C15 -179.9(3) . . . . ?
C16 C15 C14 C13 -0.4(6) . . . . ?
C3 C8 C7 C6 -0.7(6) . . . . ?
C9 C8 C7 C6 178.5(4) . . . . ?
C5 C6 C7 C8 0.0(6) . . . . ?
C23 Si1 C19 C21 52.8(3) . . . . ?
C24 Si1 C19 C21 -62.3(3) . . . . ?
C1 Si1 C19 C21 174.4(3) . . . . ?
C23 Si1 C19 C22 173.1(3) . . . . ?
C24 Si1 C19 C22 58.0(3) . . . . ?
C1 Si1 C19 C22 -65.3(3) . . . . ?
C23 Si1 C19 C20 -67.1(3) . . . . ?
C24 Si1 C19 C20 177.8(3) . . . . ?
C1 Si1 C19 C20 54.4(3) . . . . ?
C14 C13 N2 O2 -179.3(3) . . . . ?
C12 C13 N2 O2 0.4(5) . . . . ?
C14 C13 N2 O1 -0.8(5) . . . . ?
C12 C13 N2 O1 178.9(4) . . . . ?
C6 C5 N1 C18 3.3(6) . . . . ?
C4 C5 N1 C18 -178.1(4) . . . . ?
C6 C5 N1 C17 173.8(4) . . . . ?
C4 C5 N1 C17 -7.6(6) . . . . ?

_refine_diff_density_max         0.843
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.140

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/methanol'
