# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_TIPS_Tetracene

loop_
_audit_creation_method
SHELXL-97
_chemical_name_systematic        
; 
 5,12-bis((triisopropylsilyl)ethynyl)tetracene 
;
_chemical_name_common            ?
_chemical_melting_point          155.4
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H52 Si2'
_chemical_formula_weight         589.00

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   14.4346(5)
_cell_length_b                   15.1821(6)
_cell_length_c                   17.0101(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3727.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    187
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.049
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6775
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29590
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         25.25
_reflns_number_total             6748
_reflns_number_gt                5482
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0951P)²+1.3009P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.11(16)
_refine_ls_number_reflns         6748
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1718
_refine_ls_wR_factor_gt          0.1538
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.26291(6) 0.70895(5) 0.41918(6) 0.0533(2) Uani 1 1 d . . .
Si2 Si 0.88916(7) 0.25486(6) 0.59389(6) 0.0625(3) Uani 1 1 d . . .
C1 C 0.2751(3) 0.8254(2) 0.4546(3) 0.0750(11) Uani 1 1 d . . .
H1A H 0.2145 0.8538 0.4488 0.090 Uiso 1 1 calc R . .
C2 C 0.3015(4) 0.8306(4) 0.5403(3) 0.1081(18) Uani 1 1 d . . .
H2A H 0.3064 0.8913 0.5558 0.162 Uiso 1 1 calc R . .
H2B H 0.3599 0.8018 0.5483 0.162 Uiso 1 1 calc R . .
H2C H 0.2548 0.8021 0.5715 0.162 Uiso 1 1 calc R . .
C3 C 0.3426(4) 0.8775(4) 0.4085(4) 0.124(2) Uani 1 1 d . . .
H3A H 0.3457 0.9363 0.4291 0.185 Uiso 1 1 calc R . .
H3B H 0.3234 0.8795 0.3545 0.185 Uiso 1 1 calc R . .
H3C H 0.4026 0.8505 0.4119 0.185 Uiso 1 1 calc R . .
C4 C 0.2448(4) 0.7069(4) 0.3089(3) 0.0933(14) Uani 1 1 d . . .
H4A H 0.2962 0.7404 0.2861 0.112 Uiso 1 1 calc R . .
C5 C 0.1552(5) 0.7560(5) 0.2849(4) 0.151(3) Uani 1 1 d . . .
H5A H 0.1485 0.7544 0.2288 0.227 Uiso 1 1 calc R . .
H5B H 0.1587 0.8161 0.3022 0.227 Uiso 1 1 calc R . .
H5C H 0.1027 0.7279 0.3090 0.227 Uiso 1 1 calc R . .
C6 C 0.2496(5) 0.6178(4) 0.2737(3) 0.130(2) Uani 1 1 d . . .
H6A H 0.2399 0.6219 0.2180 0.195 Uiso 1 1 calc R . .
H6B H 0.2026 0.5811 0.2965 0.195 Uiso 1 1 calc R . .
H6C H 0.3095 0.5927 0.2838 0.195 Uiso 1 1 calc R . .
C7 C 0.1686(3) 0.6464(4) 0.4695(4) 0.0975(16) Uani 1 1 d . . .
H7A H 0.1476 0.6016 0.4320 0.117 Uiso 1 1 calc R . .
C8 C 0.0838(4) 0.7057(6) 0.4866(6) 0.182(4) Uani 1 1 d . . .
H8A H 0.0361 0.6714 0.5114 0.272 Uiso 1 1 calc R . .
H8B H 0.0607 0.7296 0.4382 0.272 Uiso 1 1 calc R . .
H8C H 0.1018 0.7529 0.5209 0.272 Uiso 1 1 calc R . .
C9 C 0.1922(5) 0.5991(5) 0.5423(4) 0.145(3) Uani 1 1 d . . .
H9A H 0.1385 0.5686 0.5614 0.217 Uiso 1 1 calc R . .
H9B H 0.2129 0.6405 0.5812 0.217 Uiso 1 1 calc R . .
H9C H 0.2406 0.5574 0.5318 0.217 Uiso 1 1 calc R . .
C10 C 0.3723(2) 0.6513(2) 0.4396(2) 0.0543(8) Uani 1 1 d . . .
C11 C 0.4404(2) 0.6091(2) 0.45680(19) 0.0503(7) Uani 1 1 d . . .
C12 C 0.5178(2) 0.55589(19) 0.47950(18) 0.0460(7) Uani 1 1 d . . .
C13 C 0.58019(18) 0.52459(17) 0.42305(18) 0.0443(6) Uani 1 1 d . . .
C14 C 0.5729(2) 0.5468(2) 0.3427(2) 0.0581(8) Uani 1 1 d . . .
H14A H 0.5245 0.5829 0.3264 0.070 Uiso 1 1 calc R . .
C15 C 0.6335(3) 0.5175(3) 0.2890(2) 0.0686(10) Uani 1 1 d . . .
H15A H 0.6273 0.5342 0.2367 0.082 Uiso 1 1 calc R . .
C16 C 0.7066(2) 0.4614(2) 0.3117(2) 0.0637(9) Uani 1 1 d . . .
H16A H 0.7478 0.4405 0.2740 0.076 Uiso 1 1 calc R . .
C17 C 0.7175(2) 0.4378(2) 0.3871(2) 0.0556(8) Uani 1 1 d . . .
H17A H 0.7665 0.4013 0.4010 0.067 Uiso 1 1 calc R . .
C18 C 0.65504(19) 0.46777(18) 0.4467(2) 0.0461(7) Uani 1 1 d . . .
C19 C 0.66419(19) 0.4434(2) 0.52583(19) 0.0470(7) Uani 1 1 d . . .
C20 C 0.60282(18) 0.47627(18) 0.58403(19) 0.0463(6) Uani 1 1 d . . .
C21 C 0.6115(2) 0.4544(2) 0.6634(2) 0.0550(8) Uani 1 1 d . . .
H21A H 0.6580 0.4155 0.6786 0.066 Uiso 1 1 calc R . .
C22 C 0.5527(2) 0.4889(2) 0.7204(2) 0.0583(8) Uani 1 1 d . . .
C23 C 0.5629(3) 0.4686(3) 0.8025(2) 0.0762(11) Uani 1 1 d . . .
H23A H 0.6082 0.4287 0.8180 0.091 Uiso 1 1 calc R . .
C24 C 0.5087(3) 0.5058(4) 0.8576(3) 0.0905(14) Uani 1 1 d . . .
H24A H 0.5162 0.4915 0.9104 0.109 Uiso 1 1 calc R . .
C25 C 0.4398(3) 0.5673(4) 0.8341(3) 0.0957(15) Uani 1 1 d . . .
H25A H 0.4034 0.5942 0.8722 0.115 Uiso 1 1 calc R . .
C26 C 0.4261(3) 0.5874(3) 0.7580(3) 0.0799(12) Uani 1 1 d . . .
H26A H 0.3798 0.6271 0.7443 0.096 Uiso 1 1 calc R . .
C27 C 0.4822(2) 0.5485(2) 0.6981(2) 0.0575(8) Uani 1 1 d . . .
C28 C 0.4709(2) 0.5693(2) 0.6194(2) 0.0557(8) Uani 1 1 d . . .
H28A H 0.4232 0.6073 0.6049 0.067 Uiso 1 1 calc R . .
C29 C 0.52915(19) 0.53493(18) 0.56086(18) 0.0457(7) Uani 1 1 d . . .
C30 C 0.7376(2) 0.3846(2) 0.54866(19) 0.0519(7) Uani 1 1 d . . .
C31 C 0.7987(2) 0.3346(2) 0.5667(2) 0.0613(9) Uani 1 1 d . . .
C32 C 0.8319(5) 0.1883(4) 0.6799(4) 0.120(2) Uani 1 1 d . . .
H32A H 0.7775 0.1583 0.6581 0.144 Uiso 1 1 calc R . .
C33 C 0.8002(5) 0.2419(4) 0.7438(3) 0.124(2) Uani 1 1 d . . .
H33A H 0.7728 0.2051 0.7834 0.186 Uiso 1 1 calc R . .
H33B H 0.7549 0.2831 0.7249 0.186 Uiso 1 1 calc R . .
H33C H 0.8516 0.2734 0.7659 0.186 Uiso 1 1 calc R . .
C34 C 0.9003(8) 0.1154(6) 0.7082(5) 0.230(6) Uani 1 1 d . . .
H34A H 0.8723 0.0823 0.7500 0.345 Uiso 1 1 calc R . .
H34B H 0.9563 0.1424 0.7268 0.345 Uiso 1 1 calc R . .
H34C H 0.9143 0.0768 0.6652 0.345 Uiso 1 1 calc R . .
C35 C 0.9926(4) 0.3126(3) 0.6285(4) 0.1059(17) Uani 1 1 d . . .
H35A H 0.9829 0.3237 0.6846 0.127 Uiso 1 1 calc R . .
C36 C 1.0140(4) 0.3994(4) 0.5926(5) 0.144(3) Uani 1 1 d . . .
H36A H 1.0697 0.4226 0.6156 0.216 Uiso 1 1 calc R . .
H36B H 0.9637 0.4393 0.6021 0.216 Uiso 1 1 calc R . .
H36C H 1.0226 0.3923 0.5370 0.216 Uiso 1 1 calc R . .
C37 C 1.0811(4) 0.2542(5) 0.6224(6) 0.193(4) Uani 1 1 d . . .
H37A H 1.1337 0.2867 0.6412 0.290 Uiso 1 1 calc R . .
H37B H 1.0911 0.2378 0.5686 0.290 Uiso 1 1 calc R . .
H37C H 1.0731 0.2022 0.6537 0.290 Uiso 1 1 calc R . .
C38 C 0.9048(4) 0.1777(3) 0.5113(3) 0.1017(18) Uani 1 1 d . . .
H38A H 0.9507 0.1338 0.5277 0.122 Uiso 1 1 calc R . .
C39 C 0.8230(6) 0.1305(6) 0.4867(7) 0.218(6) Uani 1 1 d . . .
H39A H 0.8384 0.0921 0.4438 0.328 Uiso 1 1 calc R . .
H39B H 0.7765 0.1717 0.4701 0.328 Uiso 1 1 calc R . .
H39C H 0.7998 0.0962 0.5298 0.328 Uiso 1 1 calc R . .
C40 C 0.9420(7) 0.2221(6) 0.4376(3) 0.183(4) Uani 1 1 d . . .
H40A H 0.9496 0.1790 0.3968 0.274 Uiso 1 1 calc R . .
H40B H 1.0007 0.2489 0.4490 0.274 Uiso 1 1 calc R . .
H40C H 0.8991 0.2665 0.4205 0.274 Uiso 1 1 calc R . .


_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 1.839(3) . ?
Si1 C7 1.867(5) . ?
Si1 C1 1.876(4) . ?
Si1 C4 1.895(4) . ?
Si2 C35 1.829(5) . ?
Si2 C31 1.840(3) . ?
Si2 C38 1.843(4) . ?
Si2 C32 1.962(6) . ?
C1 C3 1.481(7) . ?
C1 C2 1.509(7) . ?
C4 C6 1.480(7) . ?
C4 C5 1.547(7) . ?
C7 C9 1.471(9) . ?
C7 C8 1.548(7) . ?
C10 C11 1.208(4) . ?
C11 C12 1.433(4) . ?
C12 C13 1.399(4) . ?
C12 C29 1.429(4) . ?
C13 C14 1.412(5) . ?
C13 C18 1.440(4) . ?
C14 C15 1.339(5) . ?
C15 C16 1.411(5) . ?
C16 C17 1.340(5) . ?
C17 C18 1.430(4) . ?
C18 C19 1.403(5) . ?
C19 C20 1.419(4) . ?
C19 C30 1.440(4) . ?
C20 C21 1.396(5) . ?
C20 C29 1.442(4) . ?
C21 C22 1.391(5) . ?
C22 C27 1.414(5) . ?
C22 C23 1.437(5) . ?
C23 C24 1.345(6) . ?
C24 C25 1.420(7) . ?
C25 C26 1.344(6) . ?
C26 C27 1.430(5) . ?
C27 C28 1.384(5) . ?
C28 C29 1.405(4) . ?
C30 C31 1.202(4) . ?
C32 C33 1.433(8) . ?
C32 C34 1.558(9) . ?
C35 C36 1.484(8) . ?
C35 C37 1.559(7) . ?
C38 C39 1.442(9) . ?
C38 C40 1.522(9) . ?

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 C7 107.3(2) . . ?
C10 Si1 C1 107.90(16) . . ?
C7 Si1 C1 113.6(2) . . ?
C10 Si1 C4 107.30(19) . . ?
C7 Si1 C4 110.2(3) . . ?
C1 Si1 C4 110.3(2) . . ?
C35 Si2 C31 110.2(2) . . ?
C35 Si2 C38 116.8(3) . . ?
C31 Si2 C38 108.26(19) . . ?
C35 Si2 C32 110.6(3) . . ?
C31 Si2 C32 103.2(2) . . ?
C38 Si2 C32 107.0(3) . . ?
C3 C1 C2 108.5(4) . . ?
C3 C1 Si1 113.3(4) . . ?
C2 C1 Si1 112.6(3) . . ?
C6 C4 C5 111.9(5) . . ?
C6 C4 Si1 114.1(4) . . ?
C5 C4 Si1 111.6(4) . . ?
C9 C7 C8 108.0(5) . . ?
C9 C7 Si1 117.7(4) . . ?
C8 C7 Si1 111.5(4) . . ?
C11 C10 Si1 174.9(3) . . ?
C10 C11 C12 176.9(3) . . ?
C13 C12 C29 121.0(3) . . ?
C13 C12 C11 120.6(3) . . ?
C29 C12 C11 118.4(3) . . ?
C12 C13 C14 122.4(3) . . ?
C12 C13 C18 119.7(3) . . ?
C14 C13 C18 118.0(3) . . ?
C15 C14 C13 122.1(3) . . ?
C14 C15 C16 120.2(4) . . ?
C17 C16 C15 120.7(3) . . ?
C16 C17 C18 121.3(3) . . ?
C19 C18 C17 122.5(3) . . ?
C19 C18 C13 119.8(3) . . ?
C17 C18 C13 117.8(3) . . ?
C18 C19 C20 121.2(3) . . ?
C18 C19 C30 119.5(3) . . ?
C20 C19 C30 119.3(3) . . ?
C21 C20 C19 122.3(3) . . ?
C21 C20 C29 118.5(3) . . ?
C19 C20 C29 119.1(3) . . ?
C22 C21 C20 122.0(3) . . ?
C21 C22 C27 119.5(3) . . ?
C21 C22 C23 122.4(3) . . ?
C27 C22 C23 118.1(3) . . ?
C24 C23 C22 121.9(4) . . ?
C23 C24 C25 119.1(4) . . ?
C26 C25 C24 121.6(4) . . ?
C25 C26 C27 120.6(4) . . ?
C28 C27 C22 119.4(3) . . ?
C28 C27 C26 121.9(3) . . ?
C22 C27 C26 118.7(3) . . ?
C27 C28 C29 122.0(3) . . ?
C28 C29 C12 122.4(3) . . ?
C28 C29 C20 118.5(3) . . ?
C12 C29 C20 119.1(3) . . ?
C31 C30 C19 178.9(4) . . ?
C30 C31 Si2 177.9(3) . . ?
C33 C32 C34 111.8(6) . . ?
C33 C32 Si2 114.1(4) . . ?
C34 C32 Si2 109.2(5) . . ?
C36 C35 C37 107.8(6) . . ?
C36 C35 Si2 117.6(4) . . ?
C37 C35 Si2 112.0(4) . . ?
C39 C38 C40 105.7(7) . . ?
C39 C38 Si2 115.9(5) . . ?
C40 C38 Si2 112.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.688
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.045
_database_code_depnum_ccdc_archive 'CCDC 1008540'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_TIPS-TCDAT

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 1,2,3,4-tetrachloro-6, 11-bis((triisopropylsilyl)ethynyl)-5,12-diazatetracene 
;
_chemical_name_common            ?
_chemical_melting_point          179.5
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H46 Cl4 N2 Si2'
_chemical_formula_weight         728.75

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   35.551(4)
_cell_length_b                   15.1706(16)
_cell_length_c                   14.9907(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.265(2)
_cell_angle_gamma                90.00
_cell_volume                     7835.7(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    140
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3072
_exptl_absorpt_coefficient_mu    0.392
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5617
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28076
_diffrn_reflns_av_R_equivalents  0.1350
_diffrn_reflns_av_sigmaI/netI    0.1310
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.18
_diffrn_reflns_theta_max         25.25
_reflns_number_total             7080
_reflns_number_gt                2960
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1152P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7080
_refine_ls_number_parameters     453
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1967
_refine_ls_R_factor_gt           0.0806
_refine_ls_wR_factor_ref         0.2584
_refine_ls_wR_factor_gt          0.1846
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.052
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.08955(4) 0.47595(11) 0.12957(11) 0.0594(5) Uani 1 1 d . . .
Si2 Si 0.40757(5) 0.55375(13) 0.58839(13) 0.0719(6) Uani 1 1 d . B .
Cl1 Cl 0.33664(5) 0.23223(12) 0.49603(12) 0.0868(6) Uani 1 1 d . . .
Cl2 Cl 0.29562(6) 0.05043(12) 0.44553(13) 0.0890(6) Uani 1 1 d . . .
Cl3 Cl 0.21146(6) 0.04155(12) 0.32656(13) 0.0940(6) Uani 1 1 d . . .
Cl4 Cl 0.16540(5) 0.21397(12) 0.25733(12) 0.0837(6) Uani 1 1 d . . .
N1 N 0.20958(12) 0.3763(3) 0.3166(3) 0.0537(12) Uani 1 1 d . . .
N2 N 0.28748(12) 0.3841(4) 0.4246(3) 0.0560(12) Uani 1 1 d . . .
C1 C 0.16646(15) 0.5252(4) 0.2576(4) 0.0568(15) Uani 1 1 d . . .
C2 C 0.13470(15) 0.5137(4) 0.2100(4) 0.0616(16) Uani 1 1 d . . .
C3 C 0.05411(15) 0.5689(4) 0.1019(4) 0.0622(16) Uani 1 1 d . . .
H3A H 0.0311 0.5460 0.0578 0.075 Uiso 1 1 calc R . .
C4 C 0.0406(2) 0.6023(5) 0.1834(5) 0.097(2) Uani 1 1 d . . .
H4A H 0.0225 0.6496 0.1642 0.146 Uiso 1 1 calc R . .
H4B H 0.0626 0.6233 0.2296 0.146 Uiso 1 1 calc R . .
H4C H 0.0283 0.5553 0.2082 0.146 Uiso 1 1 calc R . .
C5 C 0.0694(2) 0.6454(5) 0.0539(5) 0.098(2) Uani 1 1 d . . .
H5A H 0.0503 0.6914 0.0408 0.147 Uiso 1 1 calc R . .
H5B H 0.0745 0.6248 -0.0025 0.147 Uiso 1 1 calc R . .
H5C H 0.0929 0.6677 0.0935 0.147 Uiso 1 1 calc R . .
C6 C 0.07130(19) 0.3793(5) 0.1832(5) 0.086(2) Uani 1 1 d . . .
H6A H 0.0854 0.3294 0.1657 0.103 Uiso 1 1 calc R . .
C7 C 0.0811(2) 0.3747(6) 0.2862(5) 0.122(3) Uani 1 1 d . . .
H7A H 0.0708 0.3214 0.3051 0.183 Uiso 1 1 calc R . .
H7B H 0.0701 0.4246 0.3101 0.183 Uiso 1 1 calc R . .
H7C H 0.1088 0.3752 0.3096 0.183 Uiso 1 1 calc R . .
C8 C 0.02818(19) 0.3567(5) 0.1399(5) 0.110(3) Uani 1 1 d . . .
H8A H 0.0210 0.3055 0.1696 0.165 Uiso 1 1 calc R . .
H8B H 0.0246 0.3451 0.0754 0.165 Uiso 1 1 calc R . .
H8C H 0.0121 0.4055 0.1480 0.165 Uiso 1 1 calc R . .
C9 C 0.10534(18) 0.4433(5) 0.0229(4) 0.082(2) Uani 1 1 d . . .
H9A H 0.1163 0.4966 0.0021 0.098 Uiso 1 1 calc R . .
C10 C 0.0707(2) 0.4161(6) -0.0567(5) 0.120(3) Uani 1 1 d . . .
H10A H 0.0799 0.4007 -0.1097 0.179 Uiso 1 1 calc R . .
H10B H 0.0528 0.4645 -0.0718 0.179 Uiso 1 1 calc R . .
H10C H 0.0578 0.3663 -0.0382 0.179 Uiso 1 1 calc R . .
C11 C 0.1369(2) 0.3750(5) 0.0385(5) 0.098(2) Uani 1 1 d . . .
H11A H 0.1435 0.3626 -0.0186 0.147 Uiso 1 1 calc R . .
H11B H 0.1280 0.3221 0.0617 0.147 Uiso 1 1 calc R . .
H11C H 0.1594 0.3968 0.0823 0.147 Uiso 1 1 calc R . .
C12 C 0.32457(15) 0.5457(4) 0.4735(3) 0.0543(15) Uani 1 1 d . . .
C13 C 0.35714(17) 0.5502(4) 0.5190(4) 0.0677(17) Uani 1 1 d . . .
C14 C 0.4053(3) 0.6071(7) 0.7009(6) 0.120(3) Uani 1 1 d D . .
H14 H 0.4313 0.6009 0.7414 0.144 Uiso 1 1 calc R A 1
C15 C 0.3782(4) 0.5645(12) 0.7519(9) 0.165(7) Uani 0.747(15) 1 d P B 1
H15A H 0.3793 0.5963 0.8079 0.247 Uiso 0.747(15) 1 calc PR B 1
H15B H 0.3860 0.5045 0.7663 0.247 Uiso 0.747(15) 1 calc PR B 1
H15C H 0.3522 0.5656 0.7140 0.247 Uiso 0.747(15) 1 calc PR B 1
C16 C 0.3973(7) 0.6999(10) 0.6971(16) 0.189(11) Uani 0.747(15) 1 d P B 1
H16A H 0.3966 0.7206 0.7572 0.284 Uiso 0.747(15) 1 calc PR B 1
H16B H 0.3726 0.7107 0.6550 0.284 Uiso 0.747(15) 1 calc PR B 1
H16C H 0.4172 0.7305 0.6766 0.284 Uiso 0.747(15) 1 calc PR B 1
C15' C 0.4457(6) 0.620(3) 0.763(2) 0.17(2) Uani 0.253(15) 1 d PD B 2
H15D H 0.4439 0.6467 0.8196 0.253 Uiso 0.253(15) 1 calc PR B 2
H15E H 0.4607 0.6565 0.7327 0.253 Uiso 0.253(15) 1 calc PR B 2
H15F H 0.4582 0.5632 0.7758 0.253 Uiso 0.253(15) 1 calc PR B 2
C16' C 0.3842(15) 0.696(2) 0.678(4) 0.29(7) Uani 0.253(15) 1 d PD B 2
H16D H 0.3828 0.7245 0.7346 0.442 Uiso 0.253(15) 1 calc PR B 2
H16E H 0.3585 0.6859 0.6411 0.442 Uiso 0.253(15) 1 calc PR B 2
H16F H 0.3983 0.7324 0.6456 0.442 Uiso 0.253(15) 1 calc PR B 2
C17 C 0.4353(2) 0.6243(7) 0.5272(7) 0.136(4) Uani 1 1 d D . .
H17A H 0.4250 0.6827 0.5359 0.164 Uiso 1 1 calc R B .
C18 C 0.4268(3) 0.6194(8) 0.4258(7) 0.180(5) Uani 1 1 d D B .
H18A H 0.4428 0.6609 0.4037 0.269 Uiso 1 1 calc R . .
H18B H 0.4000 0.6331 0.4001 0.269 Uiso 1 1 calc R . .
H18C H 0.4322 0.5609 0.4077 0.269 Uiso 1 1 calc R . .
C19 C 0.4779(2) 0.6361(8) 0.5752(8) 0.195(6) Uani 1 1 d . B .
H19A H 0.4899 0.6735 0.5387 0.293 Uiso 1 1 calc R . .
H19B H 0.4905 0.5797 0.5829 0.293 Uiso 1 1 calc R . .
H19C H 0.4801 0.6626 0.6345 0.293 Uiso 1 1 calc R . .
C20 C 0.4247(3) 0.4381(7) 0.6080(8) 0.149(4) Uani 1 1 d D . .
H20 H 0.4059 0.4171 0.6413 0.179 Uiso 1 1 calc R B 1
C21 C 0.4615(4) 0.4207(11) 0.6815(12) 0.203(11) Uani 0.679(17) 1 d PD B 1
H21A H 0.4667 0.3585 0.6853 0.305 Uiso 0.679(17) 1 calc PR B 1
H21B H 0.4585 0.4416 0.7398 0.305 Uiso 0.679(17) 1 calc PR B 1
H21C H 0.4828 0.4509 0.6660 0.305 Uiso 0.679(17) 1 calc PR B 1
C22 C 0.4178(6) 0.3749(16) 0.5372(18) 0.192(14) Uani 0.679(17) 1 d P B 1
H22A H 0.4283 0.3191 0.5618 0.288 Uiso 0.679(17) 1 calc PR B 1
H22B H 0.4301 0.3931 0.4900 0.288 Uiso 0.679(17) 1 calc PR B 1
H22C H 0.3904 0.3692 0.5116 0.288 Uiso 0.679(17) 1 calc PR B 1
C21' C 0.4067(12) 0.391(2) 0.677(3) 0.22(3) Uani 0.321(17) 1 d PD B 2
H21D H 0.4163 0.3313 0.6850 0.324 Uiso 0.321(17) 1 calc PR B 2
H21E H 0.3790 0.3898 0.6543 0.324 Uiso 0.321(17) 1 calc PR B 2
H21F H 0.4135 0.4210 0.7348 0.324 Uiso 0.321(17) 1 calc PR B 2
C22' C 0.4261(18) 0.406(3) 0.5115(19) 0.21(3) Uani 0.321(17) 1 d PD B 2
H22D H 0.4345 0.3452 0.5151 0.319 Uiso 0.321(17) 1 calc PR B 2
H22E H 0.4440 0.4411 0.4885 0.319 Uiso 0.321(17) 1 calc PR B 2
H22F H 0.4007 0.4100 0.4706 0.319 Uiso 0.321(17) 1 calc PR B 2
C23 C 0.20603(14) 0.5323(4) 0.3127(3) 0.0519(14) Uani 1 1 d . . .
C24 C 0.22376(14) 0.6152(4) 0.3363(4) 0.0530(15) Uani 1 1 d . . .
C25 C 0.20385(17) 0.6946(5) 0.3084(4) 0.0676(17) Uani 1 1 d . . .
H25A H 0.1783 0.6928 0.2737 0.081 Uiso 1 1 calc R . .
C26 C 0.22142(19) 0.7737(5) 0.3313(5) 0.079(2) Uani 1 1 d . . .
H26A H 0.2081 0.8254 0.3105 0.094 Uiso 1 1 calc R . .
C27 C 0.25993(18) 0.7780(5) 0.3866(4) 0.077(2) Uani 1 1 d . . .
H27A H 0.2713 0.8326 0.4038 0.093 Uiso 1 1 calc R . .
C28 C 0.28002(17) 0.7042(5) 0.4143(4) 0.0645(17) Uani 1 1 d . . .
H28A H 0.3054 0.7086 0.4495 0.077 Uiso 1 1 calc R . .
C29 C 0.26358(15) 0.6189(4) 0.3913(4) 0.0534(15) Uani 1 1 d . . .
C30 C 0.28451(14) 0.5423(4) 0.4195(3) 0.0532(15) Uani 1 1 d . . .
C31 C 0.26676(14) 0.4579(4) 0.3955(3) 0.0506(14) Uani 1 1 d . . .
C32 C 0.26928(16) 0.3078(4) 0.4014(4) 0.0559(15) Uani 1 1 d . . .
C33 C 0.28946(17) 0.2260(5) 0.4309(4) 0.0620(16) Uani 1 1 d . . .
C34 C 0.27184(18) 0.1473(4) 0.4091(4) 0.0628(16) Uani 1 1 d . . .
C35 C 0.23224(19) 0.1431(4) 0.3534(4) 0.0648(17) Uani 1 1 d . . .
C36 C 0.21231(17) 0.2183(4) 0.3236(4) 0.0598(16) Uani 1 1 d . . .
C37 C 0.22981(16) 0.3032(4) 0.3451(4) 0.0553(15) Uani 1 1 d . . .
C38 C 0.22712(14) 0.4537(4) 0.3407(3) 0.0502(14) 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 C2 1.845(5) . ?
Si1 C6 1.864(7) . ?
Si1 C3 1.869(6) . ?
Si1 C9 1.886(7) . ?
Si2 C13 1.838(6) . ?
Si2 C17 1.846(9) . ?
Si2 C20 1.856(9) . ?
Si2 C14 1.892(9) . ?
Cl1 C33 1.723(6) . ?
Cl2 C34 1.716(7) . ?
Cl3 C35 1.714(6) . ?
Cl4 C36 1.719(6) . ?
N1 C37 1.333(7) . ?
N1 C38 1.338(7) . ?
N2 C32 1.330(7) . ?
N2 C31 1.352(7) . ?
C1 C2 1.191(7) . ?
C1 C23 1.449(7) . ?
C3 C4 1.505(8) . ?
C3 C5 1.532(8) . ?
C6 C7 1.498(9) . ?
C6 C8 1.549(8) . ?
C9 C11 1.503(9) . ?
C9 C10 1.546(8) . ?
C12 C13 1.192(7) . ?
C12 C30 1.455(7) . ?
C14 C16 1.434(16) . ?
C14 C15 1.513(15) . ?
C14 C15' 1.521(10) . ?
C14 C16' 1.535(10) . ?
C17 C18 1.477(8) . ?
C17 C19 1.516(10) . ?
C20 C22 1.41(2) . ?
C20 C21 1.513(9) . ?
C20 C21' 1.522(10) . ?
C20 C22' 1.542(10) . ?
C23 C24 1.412(7) . ?
C23 C38 1.416(7) . ?
C24 C25 1.406(8) . ?
C24 C29 1.453(7) . ?
C25 C26 1.357(8) . ?
C26 C27 1.417(8) . ?
C27 C28 1.339(8) . ?
C28 C29 1.427(8) . ?
C29 C30 1.388(7) . ?
C30 C31 1.434(7) . ?
C31 C38 1.447(7) . ?
C32 C33 1.446(8) . ?
C32 C37 1.450(8) . ?
C33 C34 1.351(8) . ?
C34 C35 1.450(8) . ?
C35 C36 1.359(8) . ?
C36 C37 1.432(8) . ?

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
C2 Si1 C6 107.5(3) . . ?
C2 Si1 C3 110.0(3) . . ?
C6 Si1 C3 113.7(3) . . ?
C2 Si1 C9 104.0(3) . . ?
C6 Si1 C9 111.6(3) . . ?
C3 Si1 C9 109.6(3) . . ?
C13 Si2 C17 107.6(3) . . ?
C13 Si2 C20 107.3(4) . . ?
C17 Si2 C20 115.6(6) . . ?
C13 Si2 C14 105.5(3) . . ?
C17 Si2 C14 109.9(5) . . ?
C20 Si2 C14 110.4(5) . . ?
C37 N1 C38 117.7(4) . . ?
C32 N2 C31 116.5(5) . . ?
C2 C1 C23 175.2(6) . . ?
C1 C2 Si1 168.8(6) . . ?
C4 C3 C5 110.3(6) . . ?
C4 C3 Si1 113.9(4) . . ?
C5 C3 Si1 112.2(4) . . ?
C7 C6 C8 112.2(6) . . ?
C7 C6 Si1 117.6(5) . . ?
C8 C6 Si1 114.0(5) . . ?
C11 C9 C10 111.0(6) . . ?
C11 C9 Si1 114.6(5) . . ?
C10 C9 Si1 112.2(5) . . ?
C13 C12 C30 178.3(7) . . ?
C12 C13 Si2 178.3(6) . . ?
C16 C14 C15 107.2(14) . . ?
C16 C14 C15' 93(2) . . ?
C15 C14 C15' 111.6(19) . . ?
C16 C14 C16' 18(2) . . ?
C15 C14 C16' 99(3) . . ?
C15' C14 C16' 111(2) . . ?
C16 C14 Si2 115.9(12) . . ?
C15 C14 Si2 116.1(8) . . ?
C15' C14 Si2 110.8(15) . . ?
C16' C14 Si2 108(2) . . ?
C18 C17 C19 114.9(9) . . ?
C18 C17 Si2 118.9(6) . . ?
C19 C17 Si2 115.2(7) . . ?
C22 C20 C21 112.8(13) . . ?
C22 C20 C21' 100(2) . . ?
C21 C20 C21' 81.8(18) . . ?
C22 C20 C22' 27(2) . . ?
C21 C20 C22' 114(2) . . ?
C21' C20 C22' 127(3) . . ?
C22 C20 Si2 122.4(13) . . ?
C21 C20 Si2 118.1(8) . . ?
C21' C20 Si2 112.2(15) . . ?
C22' C20 Si2 103.9(18) . . ?
C24 C23 C38 120.3(5) . . ?
C24 C23 C1 121.3(5) . . ?
C38 C23 C1 118.4(5) . . ?
C25 C24 C23 121.8(5) . . ?
C25 C24 C29 119.0(5) . . ?
C23 C24 C29 119.2(5) . . ?
C26 C25 C24 121.0(6) . . ?
C25 C26 C27 120.5(6) . . ?
C28 C27 C26 120.5(6) . . ?
C27 C28 C29 121.9(6) . . ?
C30 C29 C28 121.9(5) . . ?
C30 C29 C24 121.0(5) . . ?
C28 C29 C24 117.1(5) . . ?
C29 C30 C31 120.1(5) . . ?
C29 C30 C12 121.2(5) . . ?
C31 C30 C12 118.7(5) . . ?
N2 C31 C30 119.2(5) . . ?
N2 C31 C38 121.6(5) . . ?
C30 C31 C38 119.2(5) . . ?
N2 C32 C33 119.6(5) . . ?
N2 C32 C37 122.2(6) . . ?
C33 C32 C37 118.2(6) . . ?
C34 C33 C32 121.3(6) . . ?
C34 C33 Cl1 120.9(5) . . ?
C32 C33 Cl1 117.8(5) . . ?
C33 C34 C35 120.2(6) . . ?
C33 C34 Cl2 121.2(5) . . ?
C35 C34 Cl2 118.6(5) . . ?
C36 C35 C34 120.5(6) . . ?
C36 C35 Cl3 121.2(5) . . ?
C34 C35 Cl3 118.4(5) . . ?
C35 C36 C37 121.2(5) . . ?
C35 C36 Cl4 120.8(5) . . ?
C37 C36 Cl4 118.0(5) . . ?
N1 C37 C36 120.4(5) . . ?
N1 C37 C32 121.0(6) . . ?
C36 C37 C32 118.6(6) . . ?
N1 C38 C23 118.8(5) . . ?
N1 C38 C31 121.0(5) . . ?
C23 C38 C31 120.1(5) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.569
_refine_diff_density_rms         0.202
_database_code_depnum_ccdc_archive 'CCDC 1008541'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_solid_solution(2)0.61(1a)0.39

loop_
_audit_creation_method
SHELXL-97
_chemical_name_systematic        
; 
 5,12-bis((triisopropylsilyl)ethynyl)tetracene
 6, 11-bis((triisopropylsilyl)ethynyl)-5,12-diazatetracene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C78 H102 N2 Si4'
_chemical_formula_weight         1179.98

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   14.4307(18)
_cell_length_b                   15.1331(18)
_cell_length_c                   16.975(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3706.9(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    121
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.057
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5198
_exptl_absorpt_correction_T_max  0.6652
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20987
_diffrn_reflns_av_R_equivalents  0.1521
_diffrn_reflns_av_sigmaI/netI    0.1860
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         25.25
_reflns_number_total             6553
_reflns_number_gt                3424
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1236P)²+2.4475P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_number_reflns         6553
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2493
_refine_ls_R_factor_gt           0.1491
_refine_ls_wR_factor_ref         0.3483
_refine_ls_wR_factor_gt          0.3014
_refine_ls_goodness_of_fit_ref   1.260
_refine_ls_restrained_S_all      1.260
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.89099(19) 0.25571(16) 0.40797(17) 0.0634(8) Uani 1 1 d . . .
Si2 Si 0.26412(17) 0.70894(15) 0.57881(16) 0.0559(8) Uani 1 1 d . . .
C1 C 0.7390(6) 0.3848(6) 0.4526(5) 0.051(2) Uani 1 1 d . . .
C2 C 0.8005(7) 0.3345(6) 0.4353(6) 0.063(3) Uani 1 1 d . . .
C3 C 0.8410(16) 0.1937(13) 0.3204(11) 0.201(11) Uani 1 1 d . . .
H3A H 0.7877 0.1636 0.3441 0.241 Uiso 1 1 calc R . .
C4 C 0.8999(19) 0.1163(15) 0.2931(13) 0.250(14) Uani 1 1 d . . .
H4A H 0.8705 0.0882 0.2489 0.376 Uiso 1 1 calc R . .
H4B H 0.9063 0.0746 0.3353 0.376 Uiso 1 1 calc R . .
H4C H 0.9600 0.1373 0.2777 0.376 Uiso 1 1 calc R . .
C5 C 0.8007(12) 0.2394(11) 0.2606(9) 0.145(6) Uani 1 1 d . . .
H5A H 0.7789 0.1988 0.2213 0.217 Uiso 1 1 calc R . .
H5B H 0.8452 0.2788 0.2376 0.217 Uiso 1 1 calc R . .
H5C H 0.7494 0.2729 0.2808 0.217 Uiso 1 1 calc R . .
C6 C 0.9939(9) 0.3150(9) 0.3763(11) 0.140(6) Uani 1 1 d . . .
H6A H 0.9827 0.3259 0.3202 0.169 Uiso 1 1 calc R . .
C7 C 1.0824(10) 0.2551(11) 0.3767(13) 0.186(9) Uani 1 1 d . . .
H7A H 1.1349 0.2890 0.3596 0.278 Uiso 1 1 calc R . .
H7B H 1.0733 0.2060 0.3418 0.278 Uiso 1 1 calc R . .
H7C H 1.0933 0.2337 0.4291 0.278 Uiso 1 1 calc R . .
C8 C 1.0147(10) 0.4021(10) 0.4075(12) 0.159(7) Uani 1 1 d . . .
H8A H 1.0710 0.4236 0.3843 0.239 Uiso 1 1 calc R . .
H8B H 1.0219 0.3985 0.4636 0.239 Uiso 1 1 calc R . .
H8C H 0.9649 0.4418 0.3951 0.239 Uiso 1 1 calc R . .
C9 C 0.9068(11) 0.1768(9) 0.4888(9) 0.121(6) Uani 1 1 d . . .
H9A H 0.9523 0.1328 0.4717 0.146 Uiso 1 1 calc R . .
C10 C 0.9466(16) 0.2239(14) 0.5627(9) 0.195(11) Uani 1 1 d . . .
H10A H 0.9543 0.1816 0.6044 0.292 Uiso 1 1 calc R . .
H10B H 0.9045 0.2693 0.5794 0.292 Uiso 1 1 calc R . .
H10C H 1.0054 0.2498 0.5501 0.292 Uiso 1 1 calc R . .
C11 C 0.8260(15) 0.1303(13) 0.5152(17) 0.249(16) Uani 1 1 d . . .
H11A H 0.8426 0.0912 0.5575 0.373 Uiso 1 1 calc R . .
H11B H 0.8007 0.0966 0.4724 0.373 Uiso 1 1 calc R . .
H11C H 0.7806 0.1719 0.5335 0.373 Uiso 1 1 calc R . .
C12 C 0.4423(6) 0.6091(6) 0.5430(5) 0.050(2) Uani 1 1 d . . .
C13 C 0.3746(7) 0.6521(6) 0.5602(5) 0.056(2) Uani 1 1 d . . .
C14 C 0.2429(10) 0.7047(10) 0.6906(7) 0.106(4) Uani 1 1 d . . .
H14A H 0.2938 0.7389 0.7137 0.128 Uiso 1 1 calc R . .
C15 C 0.2488(13) 0.6209(10) 0.7267(8) 0.142(6) Uani 1 1 d . . .
H15A H 0.2371 0.6266 0.7821 0.212 Uiso 1 1 calc R . .
H15B H 0.3096 0.5969 0.7187 0.212 Uiso 1 1 calc R . .
H15C H 0.2036 0.5821 0.7038 0.212 Uiso 1 1 calc R . .
C16 C 0.1538(10) 0.7579(12) 0.7110(10) 0.162(7) Uani 1 1 d . . .
H16A H 0.1433 0.7558 0.7668 0.243 Uiso 1 1 calc R . .
H16B H 0.1017 0.7326 0.6841 0.243 Uiso 1 1 calc R . .
H16C H 0.1615 0.8182 0.6948 0.243 Uiso 1 1 calc R . .
C17 C 0.2756(8) 0.8251(6) 0.5432(8) 0.083(3) Uani 1 1 d . . .
H17A H 0.2147 0.8533 0.5479 0.100 Uiso 1 1 calc R . .
C18 C 0.3425(10) 0.8771(9) 0.5921(10) 0.131(6) Uani 1 1 d . . .
H18A H 0.3465 0.9363 0.5721 0.196 Uiso 1 1 calc R . .
H18B H 0.4025 0.8498 0.5899 0.196 Uiso 1 1 calc R . .
H18C H 0.3214 0.8786 0.6457 0.196 Uiso 1 1 calc R . .
C19 C 0.3046(10) 0.8308(9) 0.4591(9) 0.125(5) Uani 1 1 d . . .
H19A H 0.3094 0.8918 0.4438 0.187 Uiso 1 1 calc R . .
H19B H 0.2595 0.8018 0.4266 0.187 Uiso 1 1 calc R . .
H19C H 0.3637 0.8026 0.4526 0.187 Uiso 1 1 calc R . .
C20 C 0.1727(9) 0.6467(9) 0.5250(10) 0.112(5) Uani 1 1 d . . .
H20A H 0.1520 0.6015 0.5625 0.134 Uiso 1 1 calc R . .
C21 C 0.1974(12) 0.5985(11) 0.4564(10) 0.155(7) Uani 1 1 d . . .
H21A H 0.1433 0.5702 0.4353 0.232 Uiso 1 1 calc R . .
H21B H 0.2428 0.5546 0.4697 0.232 Uiso 1 1 calc R . .
H21C H 0.2227 0.6382 0.4179 0.232 Uiso 1 1 calc R . .
C22 C 0.0855(9) 0.7035(13) 0.5091(13) 0.198(10) Uani 1 1 d . . .
H22A H 0.0405 0.6689 0.4812 0.297 Uiso 1 1 calc R . .
H22B H 0.1023 0.7540 0.4780 0.297 Uiso 1 1 calc R . .
H22C H 0.0597 0.7229 0.5583 0.297 Uiso 1 1 calc R . .
C23 C 0.6660(5) 0.4432(5) 0.4753(6) 0.041(2) Uani 1 1 d . . .
C24 C 0.6559(5) 0.4676(5) 0.5542(6) 0.047(2) Uani 1 1 d . . .
C25 C 0.7190(6) 0.4381(6) 0.6138(6) 0.057(3) Uani 1 1 d . . .
H25A H 0.7685 0.4019 0.6000 0.068 Uiso 1 1 calc R . .
C26 C 0.7073(7) 0.4620(6) 0.6890(6) 0.061(3) Uani 1 1 d . . .
H26A H 0.7485 0.4412 0.7269 0.073 Uiso 1 1 calc R . .
C27 C 0.6347(7) 0.5176(7) 0.7122(6) 0.068(3) Uani 1 1 d . . .
H27A H 0.6289 0.5338 0.7648 0.081 Uiso 1 1 calc R . .
C28 C 0.5735(7) 0.5477(6) 0.6590(6) 0.058(3) Uani 1 1 d . . .
H28A H 0.5251 0.5840 0.6752 0.069 Uiso 1 1 calc R . .
C29 C 0.5820(5) 0.5247(5) 0.5784(6) 0.044(2) Uani 1 1 d . . .
C30 C 0.5194(5) 0.5571(5) 0.5217(5) 0.043(2) Uani 1 1 d . . .
C31 C 0.5309(6) 0.5339(5) 0.4399(5) 0.044(2) Uani 1 1 d . . .
C32 C 0.4736(6) 0.5687(6) 0.3834(6) 0.064(3) Uani 0.50 1 d P . .
H32A H 0.4271 0.6079 0.3983 0.076 Uiso 0.50 1 calc PR . .
N1 N 0.4736(6) 0.5687(6) 0.3834(6) 0.064(3) Uani 0.50 1 d P . .
C33 C 0.4834(6) 0.5469(6) 0.3052(6) 0.058(3) Uani 1 1 d . . .
C34 C 0.4275(8) 0.5858(9) 0.2446(8) 0.087(4) Uani 1 1 d . . .
H34A H 0.3813 0.6259 0.2580 0.104 Uiso 1 1 calc R . .
C35 C 0.4412(10) 0.5650(10) 0.1697(8) 0.102(4) Uani 1 1 d . . .
H35A H 0.4049 0.5924 0.1316 0.123 Uiso 1 1 calc R . .
C36 C 0.5089(9) 0.5025(10) 0.1451(8) 0.097(4) Uani 1 1 d . . .
H36A H 0.5151 0.4875 0.0922 0.117 Uiso 1 1 calc R . .
C37 C 0.5646(8) 0.4651(8) 0.2010(7) 0.083(3) Uani 1 1 d . . .
H37A H 0.6098 0.4247 0.1857 0.100 Uiso 1 1 calc R . .
C38 C 0.5549(7) 0.4868(7) 0.2831(6) 0.065(3) Uani 1 1 d . . .
C39 C 0.6143(6) 0.4530(5) 0.3384(6) 0.061(2) Uani 0.50 1 d P . .
H39A H 0.6613 0.4145 0.3235 0.073 Uiso 0.50 1 calc PR . .
N2 N 0.6143(6) 0.4530(5) 0.3384(6) 0.061(2) Uani 0.50 1 d P . .
C40 C 0.6040(5) 0.4765(5) 0.4166(5) 0.045(2) 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 C6 1.816(14) . ?
Si1 C2 1.828(10) . ?
Si1 C9 1.833(12) . ?
Si1 C3 1.900(19) . ?
Si2 C13 1.839(10) . ?
Si2 C20 1.861(13) . ?
Si2 C17 1.867(10) . ?
Si2 C14 1.924(12) . ?
C1 C2 1.206(11) . ?
C1 C23 1.427(12) . ?
C3 C5 1.36(2) . ?
C3 C4 1.52(2) . ?
C6 C8 1.452(19) . ?
C6 C7 1.567(17) . ?
C9 C11 1.43(2) . ?
C9 C10 1.55(2) . ?
C12 C13 1.211(11) . ?
C12 C30 1.409(12) . ?
C14 C15 1.411(17) . ?
C14 C16 1.556(18) . ?
C17 C19 1.492(17) . ?
C17 C18 1.496(17) . ?
C20 C21 1.42(2) . ?
C20 C22 1.548(18) . ?
C23 C24 1.397(12) . ?
C23 C40 1.431(12) . ?
C24 C25 1.432(12) . ?
C24 C29 1.434(11) . ?
C25 C26 1.339(12) . ?
C26 C27 1.400(13) . ?
C27 C28 1.343(13) . ?
C28 C29 1.417(12) . ?
C29 C30 1.408(11) . ?
C30 C31 1.441(11) . ?
C31 C32 1.372(11) . ?
C31 C40 1.422(11) . ?
C32 C33 1.375(12) . ?
C33 C38 1.425(13) . ?
C33 C34 1.433(14) . ?
C34 C35 1.325(16) . ?
C35 C36 1.423(18) . ?
C36 C37 1.367(16) . ?
C37 C38 1.439(14) . ?
C38 C39 1.370(13) . ?
C39 C40 1.381(12) . ?

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
C6 Si1 C2 109.7(5) . . ?
C6 Si1 C9 116.2(8) . . ?
C2 Si1 C9 108.9(5) . . ?
C6 Si1 C3 108.8(10) . . ?
C2 Si1 C3 104.5(6) . . ?
C9 Si1 C3 108.1(9) . . ?
C13 Si2 C20 107.0(5) . . ?
C13 Si2 C17 107.9(4) . . ?
C20 Si2 C17 112.4(6) . . ?
C13 Si2 C14 107.0(5) . . ?
C20 Si2 C14 110.8(7) . . ?
C17 Si2 C14 111.4(6) . . ?
C2 C1 C23 178.4(10) . . ?
C1 C2 Si1 178.1(9) . . ?
C5 C3 C4 113.8(17) . . ?
C5 C3 Si1 119.7(14) . . ?
C4 C3 Si1 114.0(15) . . ?
C8 C6 C7 110.8(14) . . ?
C8 C6 Si1 120.6(12) . . ?
C7 C6 Si1 112.3(10) . . ?
C11 C9 C10 105.8(17) . . ?
C11 C9 Si1 116.9(14) . . ?
C10 C9 Si1 110.6(11) . . ?
C13 C12 C30 178.2(10) . . ?
C12 C13 Si2 173.4(8) . . ?
C15 C14 C16 114.7(13) . . ?
C15 C14 Si2 116.7(10) . . ?
C16 C14 Si2 109.5(10) . . ?
C19 C17 C18 108.6(11) . . ?
C19 C17 Si2 112.9(8) . . ?
C18 C17 Si2 111.9(9) . . ?
C21 C20 C22 110.3(14) . . ?
C21 C20 Si2 119.1(12) . . ?
C22 C20 Si2 112.3(10) . . ?
C24 C23 C1 119.9(8) . . ?
C24 C23 C40 120.6(7) . . ?
C1 C23 C40 119.5(8) . . ?
C23 C24 C25 121.9(8) . . ?
C23 C24 C29 120.8(8) . . ?
C25 C24 C29 117.3(9) . . ?
C26 C25 C24 120.6(9) . . ?
C25 C26 C27 121.7(9) . . ?
C28 C27 C26 120.5(9) . . ?
C27 C28 C29 120.6(9) . . ?
C30 C29 C28 121.3(7) . . ?
C30 C29 C24 119.4(8) . . ?
C28 C29 C24 119.3(8) . . ?
C29 C30 C12 121.7(8) . . ?
C29 C30 C31 120.0(7) . . ?
C12 C30 C31 118.3(8) . . ?
C32 C31 C40 119.1(8) . . ?
C32 C31 C30 120.7(7) . . ?
C40 C31 C30 120.2(8) . . ?
C31 C32 C33 121.4(8) . . ?
C32 C33 C38 118.7(9) . . ?
C32 C33 C34 122.4(10) . . ?
C38 C33 C34 118.8(10) . . ?
C35 C34 C33 120.5(12) . . ?
C34 C35 C36 122.8(13) . . ?
C37 C36 C35 118.4(12) . . ?
C36 C37 C38 121.3(12) . . ?
C39 C38 C33 120.7(9) . . ?
C39 C38 C37 121.1(11) . . ?
C33 C38 C37 118.1(11) . . ?
C38 C39 C40 119.6(8) . . ?
C39 C40 C31 120.3(8) . . ?
C39 C40 C23 120.7(8) . . ?
C31 C40 C23 119.0(8) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.078
_database_code_depnum_ccdc_archive 'CCDC 1008542'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_solid_solution(2)0.19(1b)0.81

loop_
_audit_creation_method
SHELXL-97
_chemical_name_systematic        
; 
 5,12-bis((triisopropylsilyl)ethynyl)tetracene
 1,2,3,4-tetrachloro-6, 11-bis((triisopropylsilyl)ethynyl)-5,12-diazatetracene 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H46 Cl4 N2 Si2'
_chemical_formula_weight         728.75

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   35.4482(19)
_cell_length_b                   15.1828(8)
_cell_length_c                   14.9575(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.9080(10)
_cell_angle_gamma                90.00
_cell_volume                     7814.2(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    162
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3072
_exptl_absorpt_coefficient_mu    0.393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6882
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41070
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         25.25
_reflns_number_total             7039
_reflns_number_gt                4101
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0978P)²+23.9056P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7039
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1275
_refine_ls_R_factor_gt           0.0751
_refine_ls_wR_factor_ref         0.2537
_refine_ls_wR_factor_gt          0.2067
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.006
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.40744(4) -0.05152(11) 1.09084(12) 0.0765(5) Uani 1 1 d . . .
Si2 Si 0.08997(4) 0.02552(11) 0.63006(10) 0.0650(4) Uani 1 1 d . . .
Cl1 Cl 0.33684(4) 0.26799(13) 0.99626(12) 0.0980(6) Uani 1 1 d . . .
Cl2 Cl 0.29591(6) 0.44962(12) 0.94532(13) 0.1016(6) Uani 1 1 d . . .
Cl3 Cl 0.21193(6) 0.45908(12) 0.82701(13) 0.1062(6) Uani 1 1 d . . .
Cl4 Cl 0.16563(4) 0.28679(12) 0.75847(12) 0.0965(6) Uani 1 1 d . . .
N1 N 0.28775(11) 0.1170(3) 0.9252(3) 0.0607(11) Uani 1 1 d . . .
N2 N 0.21002(11) 0.1258(3) 0.8178(3) 0.0632(11) Uani 1 1 d . . .
C1 C 0.32432(13) -0.0443(3) 0.9750(3) 0.0620(13) Uani 1 1 d . . .
C2 C 0.35743(15) -0.0491(4) 1.0200(4) 0.0732(15) Uani 1 1 d . . .
C3 C 0.4361(2) -0.1244(7) 1.0273(8) 0.149(4) Uani 1 1 d . . .
H3A H 0.4253 -0.1826 1.0348 0.179 Uiso 1 1 calc R . .
C4 C 0.4787(2) -0.1363(8) 1.0813(9) 0.199(5) Uani 1 1 d . . .
H4A H 0.4919 -0.1745 1.0475 0.298 Uiso 1 1 calc R . .
H4B H 0.4794 -0.1619 1.1403 0.298 Uiso 1 1 calc R . .
H4C H 0.4914 -0.0801 1.0896 0.298 Uiso 1 1 calc R . .
C5 C 0.4300(3) -0.1196(9) 0.9325(7) 0.191(6) Uani 1 1 d . . .
H5A H 0.4464 -0.1614 0.9120 0.286 Uiso 1 1 calc R . .
H5B H 0.4360 -0.0613 0.9152 0.286 Uiso 1 1 calc R . .
H5C H 0.4033 -0.1328 0.9044 0.286 Uiso 1 1 calc R . .
C6 C 0.4060(2) -0.1054(7) 1.2032(6) 0.126(3) Uani 1 1 d . . .
H6A H 0.4320 -0.1026 1.2447 0.151 Uiso 1 1 calc R . .
C7 C 0.3774(4) -0.0668(10) 1.2506(7) 0.207(6) Uani 1 1 d . . .
H7A H 0.3788 -0.0977 1.3073 0.310 Uiso 1 1 calc R . .
H7B H 0.3517 -0.0721 1.2117 0.310 Uiso 1 1 calc R . .
H7C H 0.3834 -0.0058 1.2635 0.310 Uiso 1 1 calc R . .
C8 C 0.3930(4) -0.1959(8) 1.1957(10) 0.221(6) Uani 1 1 d . . .
H8A H 0.3932 -0.2182 1.2559 0.331 Uiso 1 1 calc R . .
H8B H 0.4100 -0.2306 1.1689 0.331 Uiso 1 1 calc R . .
H8C H 0.3671 -0.1988 1.1574 0.331 Uiso 1 1 calc R . .
C9 C 0.4234(3) 0.0671(6) 1.1112(8) 0.172(5) Uani 1 1 d . . .
H9A H 0.4021 0.0922 1.1347 0.206 Uiso 1 1 calc R . .
C10 C 0.4549(6) 0.0885(9) 1.1792(12) 0.326(12) Uani 1 1 d . . .
H10A H 0.4582 0.1512 1.1813 0.489 Uiso 1 1 calc R . .
H10B H 0.4776 0.0611 1.1672 0.489 Uiso 1 1 calc R . .
H10C H 0.4512 0.0681 1.2373 0.489 Uiso 1 1 calc R . .
C11 C 0.4192(4) 0.1149(7) 1.0239(11) 0.233(7) Uani 1 1 d . . .
H11A H 0.4273 0.1749 1.0365 0.350 Uiso 1 1 calc R . .
H11B H 0.3925 0.1136 0.9902 0.350 Uiso 1 1 calc R . .
H11C H 0.4350 0.0874 0.9882 0.350 Uiso 1 1 calc R . .
C12 C 0.16722(13) -0.0223(4) 0.7581(3) 0.0637(13) Uani 1 1 d . . .
C13 C 0.13498(13) -0.0112(4) 0.7102(3) 0.0689(14) Uani 1 1 d . . .
C14 C 0.05451(14) -0.0689(4) 0.6015(4) 0.0721(15) Uani 1 1 d . . .
H14A H 0.0315 -0.0466 0.5573 0.087 Uiso 1 1 calc R . .
C15 C 0.0411(2) -0.1030(5) 0.6832(5) 0.109(2) Uani 1 1 d . . .
H15A H 0.0231 -0.1505 0.6641 0.164 Uiso 1 1 calc R . .
H15B H 0.0286 -0.0564 0.7086 0.164 Uiso 1 1 calc R . .
H15C H 0.0631 -0.1239 0.7291 0.164 Uiso 1 1 calc R . .
C16 C 0.0700(2) -0.1460(5) 0.5557(5) 0.101(2) Uani 1 1 d . . .
H16A H 0.0508 -0.1918 0.5428 0.152 Uiso 1 1 calc R . .
H16B H 0.0933 -0.1682 0.5962 0.152 Uiso 1 1 calc R . .
H16C H 0.0756 -0.1265 0.4992 0.152 Uiso 1 1 calc R . .
C17 C 0.10556(17) 0.0588(5) 0.5227(4) 0.093(2) Uani 1 1 d . . .
H17A H 0.1163 0.0055 0.5015 0.112 Uiso 1 1 calc R . .
C18 C 0.1379(2) 0.1263(5) 0.5383(5) 0.112(2) Uani 1 1 d . . .
H18A H 0.1445 0.1386 0.4810 0.168 Uiso 1 1 calc R . .
H18B H 0.1602 0.1036 0.5817 0.168 Uiso 1 1 calc R . .
H18C H 0.1294 0.1795 0.5620 0.168 Uiso 1 1 calc R . .
C19 C 0.0713(2) 0.0864(6) 0.4429(5) 0.124(3) Uani 1 1 d . . .
H19A H 0.0808 0.1012 0.3899 0.186 Uiso 1 1 calc R . .
H19B H 0.0585 0.1367 0.4612 0.186 Uiso 1 1 calc R . .
H19C H 0.0532 0.0386 0.4279 0.186 Uiso 1 1 calc R . .
C20 C 0.07112(18) 0.1221(5) 0.6826(5) 0.097(2) Uani 1 1 d . . .
H20A H 0.0850 0.1723 0.6645 0.117 Uiso 1 1 calc R . .
C21 C 0.0806(2) 0.1268(6) 0.7839(5) 0.128(3) Uani 1 1 d . . .
H21A H 0.0700 0.1800 0.8027 0.191 Uiso 1 1 calc R . .
H21B H 0.1083 0.1267 0.8071 0.191 Uiso 1 1 calc R . .
H21C H 0.0697 0.0769 0.8079 0.191 Uiso 1 1 calc R . .
C22 C 0.02807(18) 0.1430(5) 0.6403(5) 0.111(2) Uani 1 1 d . . .
H22A H 0.0207 0.1943 0.6695 0.166 Uiso 1 1 calc R . .
H22B H 0.0123 0.0940 0.6495 0.166 Uiso 1 1 calc R . .
H22C H 0.0243 0.1539 0.5756 0.166 Uiso 1 1 calc R . .
C23 C 0.26735(12) 0.0433(4) 0.8967(3) 0.0555(12) Uani 1 1 d . . .
C24 C 0.28481(12) -0.0406(4) 0.9207(3) 0.0566(12) Uani 1 1 d . . .
C25 C 0.26367(13) -0.1174(4) 0.8926(3) 0.0580(12) Uani 1 1 d . . .
C26 C 0.27982(14) -0.2030(4) 0.9143(3) 0.0686(15) Uani 1 1 d . . .
H26A H 0.3052 -0.2079 0.9492 0.082 Uiso 1 1 calc R . .
C27 C 0.25954(16) -0.2772(4) 0.8860(4) 0.0799(16) Uani 1 1 d . . .
H27A H 0.2711 -0.3318 0.9018 0.096 Uiso 1 1 calc R . .
C28 C 0.22056(16) -0.2728(4) 0.8320(4) 0.0806(16) Uani 1 1 d . . .
H28A H 0.2066 -0.3241 0.8128 0.097 Uiso 1 1 calc R . .
C29 C 0.20403(15) -0.1933(4) 0.8090(4) 0.0721(15) Uani 1 1 d . . .
H29A H 0.1787 -0.1912 0.7732 0.087 Uiso 1 1 calc R . .
C30 C 0.22365(12) -0.1128(4) 0.8368(3) 0.0587(13) Uani 1 1 d . . .
C31 C 0.20665(12) -0.0305(4) 0.8129(3) 0.0572(12) Uani 1 1 d . . .
C32 C 0.22760(12) 0.0480(4) 0.8418(3) 0.0557(12) Uani 1 1 d . . .
C33 C 0.27022(14) 0.1943(4) 0.9023(3) 0.0615(13) Uani 1 1 d . . .
C34 C 0.29058(15) 0.2750(4) 0.9318(3) 0.0680(14) Uani 1 1 d . . .
C35 C 0.27276(17) 0.3542(4) 0.9098(4) 0.0719(15) Uani 1 1 d . . .
C36 C 0.23345(17) 0.3582(4) 0.8552(4) 0.0729(15) Uani 1 1 d . . .
C37 C 0.21317(15) 0.2840(4) 0.8253(4) 0.0694(14) Uani 1 1 d . . .
C38 C 0.23038(14) 0.1989(4) 0.8468(3) 0.0625(13) 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 C2 1.834(5) . ?
Si1 C6 1.881(8) . ?
Si1 C9 1.890(9) . ?
Si1 C3 1.905(9) . ?
Si2 C13 1.837(5) . ?
Si2 C20 1.862(7) . ?
Si2 C14 1.886(5) . ?
Si2 C17 1.889(6) . ?
Cl1 C34 1.694(5) . ?
Cl2 C35 1.687(6) . ?
Cl3 C36 1.718(6) . ?
Cl4 C37 1.742(5) . ?
N1 C33 1.333(6) . ?
N1 C23 1.346(6) . ?
N2 C38 1.338(7) . ?
N2 C32 1.343(6) . ?
C1 C2 1.207(6) . ?
C1 C24 1.441(6) . ?
C3 C5 1.384(12) . ?
C3 C4 1.542(11) . ?
C6 C8 1.444(13) . ?
C6 C7 1.490(13) . ?
C9 C10 1.358(16) . ?
C9 C11 1.469(15) . ?
C12 C13 1.206(6) . ?
C12 C31 1.446(6) . ?
C14 C15 1.506(8) . ?
C14 C16 1.524(8) . ?
C17 C18 1.513(9) . ?
C17 C19 1.542(8) . ?
C20 C21 1.472(9) . ?
C20 C22 1.538(8) . ?
C23 C24 1.423(7) . ?
C23 C32 1.452(6) . ?
C24 C25 1.396(7) . ?
C25 C26 1.426(7) . ?
C25 C30 1.464(6) . ?
C26 C27 1.349(8) . ?
C27 C28 1.425(7) . ?
C28 C29 1.350(8) . ?
C29 C30 1.418(7) . ?
C30 C31 1.395(7) . ?
C31 C32 1.416(7) . ?
C33 C34 1.437(8) . ?
C33 C38 1.458(7) . ?
C34 C35 1.361(8) . ?
C35 C36 1.437(8) . ?
C36 C37 1.354(8) . ?
C37 C38 1.431(7) . ?

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
C2 Si1 C6 107.2(3) . . ?
C2 Si1 C9 106.5(4) . . ?
C6 Si1 C9 110.0(5) . . ?
C2 Si1 C3 106.3(3) . . ?
C6 Si1 C3 109.0(5) . . ?
C9 Si1 C3 117.4(6) . . ?
C13 Si2 C20 107.9(3) . . ?
C13 Si2 C14 110.1(3) . . ?
C20 Si2 C14 114.0(3) . . ?
C13 Si2 C17 104.5(3) . . ?
C20 Si2 C17 110.9(3) . . ?
C14 Si2 C17 109.1(3) . . ?
C33 N1 C23 118.0(4) . . ?
C38 N2 C32 117.6(4) . . ?
C2 C1 C24 178.7(6) . . ?
C1 C2 Si1 177.3(5) . . ?
C5 C3 C4 115.9(9) . . ?
C5 C3 Si1 120.6(7) . . ?
C4 C3 Si1 112.3(7) . . ?
C8 C6 C7 99.8(9) . . ?
C8 C6 Si1 114.9(8) . . ?
C7 C6 Si1 114.9(7) . . ?
C10 C9 C11 115.9(11) . . ?
C10 C9 Si1 120.6(9) . . ?
C11 C9 Si1 111.4(9) . . ?
C13 C12 C31 176.3(6) . . ?
C12 C13 Si2 168.7(5) . . ?
C15 C14 C16 108.6(6) . . ?
C15 C14 Si2 113.7(4) . . ?
C16 C14 Si2 113.1(4) . . ?
C18 C17 C19 111.2(6) . . ?
C18 C17 Si2 114.6(5) . . ?
C19 C17 Si2 113.2(5) . . ?
C21 C20 C22 111.9(6) . . ?
C21 C20 Si2 117.1(5) . . ?
C22 C20 Si2 114.2(5) . . ?
N1 C23 C24 119.8(4) . . ?
N1 C23 C32 120.8(4) . . ?
C24 C23 C32 119.4(4) . . ?
C25 C24 C23 120.1(4) . . ?
C25 C24 C1 121.1(4) . . ?
C23 C24 C1 118.8(4) . . ?
C24 C25 C26 122.4(4) . . ?
C24 C25 C30 120.5(5) . . ?
C26 C25 C30 117.1(5) . . ?
C27 C26 C25 122.4(5) . . ?
C26 C27 C28 120.6(6) . . ?
C29 C28 C27 119.3(6) . . ?
C28 C29 C30 122.9(5) . . ?
C31 C30 C29 123.0(4) . . ?
C31 C30 C25 119.3(5) . . ?
C29 C30 C25 117.7(5) . . ?
C30 C31 C32 120.9(4) . . ?
C30 C31 C12 121.4(5) . . ?
C32 C31 C12 117.7(5) . . ?
N2 C32 C31 118.9(4) . . ?
N2 C32 C23 121.3(5) . . ?
C31 C32 C23 119.8(4) . . ?
N1 C33 C34 120.2(4) . . ?
N1 C33 C38 121.1(5) . . ?
C34 C33 C38 118.7(5) . . ?
C35 C34 C33 120.6(5) . . ?
C35 C34 Cl1 121.5(5) . . ?
C33 C34 Cl1 117.8(4) . . ?
C34 C35 C36 120.3(5) . . ?
C34 C35 Cl2 121.3(5) . . ?
C36 C35 Cl2 118.3(5) . . ?
C37 C36 C35 121.2(5) . . ?
C37 C36 Cl3 119.5(5) . . ?
C35 C36 Cl3 119.3(5) . . ?
C36 C37 C38 120.9(5) . . ?
C36 C37 Cl4 122.2(4) . . ?
C38 C37 Cl4 116.9(4) . . ?
N2 C38 C37 120.5(4) . . ?
N2 C38 C33 121.2(5) . . ?
C37 C38 C33 118.3(5) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.060
_database_code_depnum_ccdc_archive 'CCDC 1008543'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_solid_solution(2)0.14(1b)0.86

loop_
_audit_creation_method
SHELXL-97
_chemical_name_systematic        
; 
  5,12-bis((triisopropylsilyl)ethynyl)tetracene
 1,2,3,4-tetrachloro-6, 11-bis((triisopropylsilyl)ethynyl)-5,12-diazatetracene 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H46 Cl4 N2 Si2'
_chemical_formula_weight         728.75

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   35.3907(11)
_cell_length_b                   15.1394(4)
_cell_length_c                   14.9478(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.1430(10)
_cell_angle_gamma                90.00
_cell_volume                     7766.2(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    162
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3072
_exptl_absorpt_coefficient_mu    0.395
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6548
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41588
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         25.25
_reflns_number_total             7029
_reflns_number_gt                4584
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0949P)²+12.6691P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7029
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.2066
_refine_ls_wR_factor_gt          0.1670
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.004
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.40759(3) -0.05284(8) 1.08960(9) 0.0726(4) Uani 1 1 d . . .
Si2 Si 0.08974(3) 0.02484(8) 0.62967(7) 0.0606(3) Uani 1 1 d . . .
Cl1 Cl 0.33674(3) 0.26767(9) 0.99642(9) 0.0908(4) Uani 1 1 d . . .
Cl2 Cl 0.29587(4) 0.44935(9) 0.94578(9) 0.0942(4) Uani 1 1 d . . .
Cl3 Cl 0.21180(4) 0.45876(8) 0.82685(10) 0.0981(4) Uani 1 1 d . . .
Cl4 Cl 0.16558(3) 0.28642(8) 0.75758(8) 0.0873(4) Uani 1 1 d . . .
N1 N 0.28758(8) 0.1165(2) 0.92478(19) 0.0576(8) Uani 1 1 d . . .
N2 N 0.20977(8) 0.1245(2) 0.81721(19) 0.0573(8) Uani 1 1 d . . .
C1 C 0.32427(10) -0.0448(3) 0.9741(2) 0.0610(9) Uani 1 1 d . . .
C2 C 0.35733(11) -0.0501(3) 1.0198(3) 0.0711(11) Uani 1 1 d . . .
C3 C 0.43591(16) -0.1239(5) 1.0267(6) 0.142(3) Uani 1 1 d . . .
H3A H 0.4254 -0.1824 1.0348 0.170 Uiso 1 1 calc R . .
C4 C 0.47869(17) -0.1356(6) 1.0783(7) 0.194(4) Uani 1 1 d . . .
H4A H 0.4914 -0.1739 1.0435 0.291 Uiso 1 1 calc R . .
H4B H 0.4801 -0.1611 1.1378 0.291 Uiso 1 1 calc R . .
H4C H 0.4914 -0.0791 1.0858 0.291 Uiso 1 1 calc R . .
C5 C 0.4289(3) -0.1197(6) 0.9307(6) 0.183(4) Uani 1 1 d . . .
H5A H 0.4453 -0.1614 0.9099 0.274 Uiso 1 1 calc R . .
H5B H 0.4345 -0.0612 0.9127 0.274 Uiso 1 1 calc R . .
H5C H 0.4020 -0.1335 0.9036 0.274 Uiso 1 1 calc R . .
C6 C 0.40662(16) -0.1066(5) 1.2013(4) 0.119(2) Uani 1 1 d . . .
H6A H 0.4328 -0.1036 1.2423 0.143 Uiso 1 1 calc R . .
C7 C 0.3785(3) -0.0678(8) 1.2505(6) 0.211(5) Uani 1 1 d . . .
H7A H 0.3802 -0.0993 1.3070 0.316 Uiso 1 1 calc R . .
H7B H 0.3525 -0.0724 1.2121 0.316 Uiso 1 1 calc R . .
H7C H 0.3848 -0.0068 1.2639 0.316 Uiso 1 1 calc R . .
C8 C 0.3941(3) -0.1996(6) 1.1932(8) 0.221(5) Uani 1 1 d . . .
H8A H 0.3942 -0.2224 1.2532 0.331 Uiso 1 1 calc R . .
H8B H 0.4116 -0.2335 1.1669 0.331 Uiso 1 1 calc R . .
H8C H 0.3682 -0.2035 1.1541 0.331 Uiso 1 1 calc R . .
C9 C 0.4235(2) 0.0659(5) 1.1125(6) 0.170(4) Uani 1 1 d . . .
H9A H 0.4026 0.0905 1.1372 0.204 Uiso 1 1 calc R . .
C10 C 0.4558(4) 0.0856(7) 1.1805(9) 0.325(10) Uani 1 1 d . . .
H10A H 0.4596 0.1484 1.1836 0.488 Uiso 1 1 calc R . .
H10B H 0.4782 0.0577 1.1673 0.488 Uiso 1 1 calc R . .
H10C H 0.4524 0.0645 1.2386 0.488 Uiso 1 1 calc R . .
C11 C 0.4191(3) 0.1154(6) 1.0254(8) 0.232(6) Uani 1 1 d . . .
H11A H 0.4273 0.1754 1.0389 0.347 Uiso 1 1 calc R . .
H11B H 0.3923 0.1145 0.9918 0.347 Uiso 1 1 calc R . .
H11C H 0.4348 0.0885 0.9889 0.347 Uiso 1 1 calc R . .
C12 C 0.16697(9) -0.0238(3) 0.7580(2) 0.0593(9) Uani 1 1 d . . .
C13 C 0.13478(10) -0.0127(3) 0.7101(3) 0.0643(10) Uani 1 1 d . . .
C14 C 0.05416(10) -0.0689(3) 0.6011(3) 0.0651(10) Uani 1 1 d . . .
H14A H 0.0311 -0.0462 0.5567 0.078 Uiso 1 1 calc R . .
C15 C 0.04047(14) -0.1025(4) 0.6830(4) 0.0970(15) Uani 1 1 d . . .
H15A H 0.0224 -0.1501 0.6638 0.146 Uiso 1 1 calc R . .
H15B H 0.0279 -0.0556 0.7078 0.146 Uiso 1 1 calc R . .
H15C H 0.0624 -0.1233 0.7295 0.146 Uiso 1 1 calc R . .
C16 C 0.06947(15) -0.1456(3) 0.5548(4) 0.0979(15) Uani 1 1 d . . .
H16A H 0.0503 -0.1916 0.5417 0.147 Uiso 1 1 calc R . .
H16B H 0.0929 -0.1679 0.5950 0.147 Uiso 1 1 calc R . .
H16C H 0.0749 -0.1257 0.4982 0.147 Uiso 1 1 calc R . .
C17 C 0.10551(12) 0.0572(3) 0.5222(3) 0.0839(13) Uani 1 1 d . . .
H17A H 0.1164 0.0037 0.5012 0.101 Uiso 1 1 calc R . .
C18 C 0.13762(14) 0.1257(4) 0.5382(4) 0.1009(16) Uani 1 1 d . . .
H18A H 0.1443 0.1381 0.4810 0.151 Uiso 1 1 calc R . .
H18B H 0.1601 0.1036 0.5821 0.151 Uiso 1 1 calc R . .
H18C H 0.1288 0.1789 0.5615 0.151 Uiso 1 1 calc R . .
C19 C 0.07124(17) 0.0853(4) 0.4430(3) 0.117(2) Uani 1 1 d . . .
H19A H 0.0807 0.1001 0.3899 0.176 Uiso 1 1 calc R . .
H19B H 0.0586 0.1358 0.4616 0.176 Uiso 1 1 calc R . .
H19C H 0.0529 0.0375 0.4279 0.176 Uiso 1 1 calc R . .
C20 C 0.07137(13) 0.1218(3) 0.6826(3) 0.0891(14) Uani 1 1 d . . .
H20A H 0.0854 0.1721 0.6650 0.107 Uiso 1 1 calc R . .
C21 C 0.08091(18) 0.1255(4) 0.7854(4) 0.120(2) Uani 1 1 d . . .
H21A H 0.0704 0.1786 0.8047 0.180 Uiso 1 1 calc R . .
H21B H 0.1087 0.1250 0.8091 0.180 Uiso 1 1 calc R . .
H21C H 0.0698 0.0752 0.8086 0.180 Uiso 1 1 calc R . .
C22 C 0.02791(14) 0.1430(4) 0.6399(4) 0.1083(18) Uani 1 1 d . . .
H22A H 0.0205 0.1944 0.6692 0.163 Uiso 1 1 calc R . .
H22B H 0.0122 0.0937 0.6489 0.163 Uiso 1 1 calc R . .
H22C H 0.0241 0.1540 0.5750 0.163 Uiso 1 1 calc R . .
C23 C 0.26718(9) 0.0424(3) 0.8961(2) 0.0539(9) Uani 1 1 d . . .
C24 C 0.28472(9) -0.0410(3) 0.9201(2) 0.0539(9) Uani 1 1 d . . .
C25 C 0.26379(9) -0.1183(3) 0.8918(2) 0.0562(9) Uani 1 1 d . . .
C26 C 0.28009(10) -0.2041(3) 0.9142(3) 0.0651(10) Uani 1 1 d . . .
H26A H 0.3055 -0.2089 0.9497 0.078 Uiso 1 1 calc R . .
C27 C 0.25977(12) -0.2784(3) 0.8855(3) 0.0752(12) Uani 1 1 d . . .
H27A H 0.2714 -0.3332 0.9013 0.090 Uiso 1 1 calc R . .
C28 C 0.22079(12) -0.2738(3) 0.8314(3) 0.0779(12) Uani 1 1 d . . .
H28A H 0.2070 -0.3254 0.8116 0.093 Uiso 1 1 calc R . .
C29 C 0.20385(11) -0.1941(3) 0.8087(3) 0.0697(11) Uani 1 1 d . . .
H29A H 0.1783 -0.1919 0.7734 0.084 Uiso 1 1 calc R . .
C30 C 0.22380(9) -0.1140(3) 0.8368(2) 0.0557(9) Uani 1 1 d . . .
C31 C 0.20630(9) -0.0320(3) 0.8126(2) 0.0543(9) Uani 1 1 d . . .
C32 C 0.22724(9) 0.0472(3) 0.8411(2) 0.0528(9) Uani 1 1 d . . .
C33 C 0.26975(10) 0.1928(3) 0.9016(2) 0.0577(9) Uani 1 1 d . . .
C34 C 0.29002(11) 0.2743(3) 0.9320(2) 0.0644(10) Uani 1 1 d . . .
C35 C 0.27224(12) 0.3529(3) 0.9093(3) 0.0665(10) Uani 1 1 d . . .
C36 C 0.23283(12) 0.3571(3) 0.8540(3) 0.0686(10) Uani 1 1 d . . .
C37 C 0.21279(11) 0.2829(3) 0.8240(3) 0.0637(10) Uani 1 1 d . . .
C38 C 0.23010(10) 0.1976(3) 0.8465(2) 0.0576(9) 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 C2 1.829(4) . ?
Si1 C6 1.866(6) . ?
Si1 C3 1.872(7) . ?
Si1 C9 1.890(7) . ?
Si2 C13 1.837(3) . ?
Si2 C20 1.859(5) . ?
Si2 C14 1.877(4) . ?
Si2 C17 1.889(5) . ?
Cl1 C34 1.701(4) . ?
Cl2 C35 1.705(4) . ?
Cl3 C36 1.714(4) . ?
Cl4 C37 1.723(4) . ?
N1 C33 1.320(5) . ?
N1 C23 1.346(4) . ?
N2 C32 1.332(4) . ?
N2 C38 1.334(5) . ?
C1 C2 1.205(5) . ?
C1 C24 1.436(4) . ?
C3 C5 1.396(9) . ?
C3 C4 1.532(8) . ?
C6 C8 1.472(10) . ?
C6 C7 1.493(10) . ?
C9 C10 1.364(12) . ?
C9 C11 1.478(11) . ?
C12 C13 1.200(5) . ?
C12 C31 1.436(4) . ?
C14 C15 1.510(6) . ?
C14 C16 1.517(6) . ?
C17 C18 1.514(6) . ?
C17 C19 1.534(6) . ?
C20 C21 1.492(7) . ?
C20 C22 1.548(6) . ?
C23 C24 1.415(5) . ?
C23 C32 1.453(4) . ?
C24 C25 1.394(5) . ?
C25 C26 1.428(5) . ?
C25 C30 1.455(4) . ?
C26 C27 1.347(6) . ?
C27 C28 1.420(6) . ?
C28 C29 1.353(6) . ?
C29 C30 1.415(5) . ?
C30 C31 1.395(5) . ?
C31 C32 1.418(5) . ?
C33 C34 1.444(5) . ?
C33 C38 1.445(5) . ?
C34 C35 1.350(6) . ?
C35 C36 1.439(6) . ?
C36 C37 1.347(6) . ?
C37 C38 1.433(5) . ?

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
C2 Si1 C6 107.0(2) . . ?
C2 Si1 C3 107.0(3) . . ?
C6 Si1 C3 109.1(4) . . ?
C2 Si1 C9 106.7(3) . . ?
C6 Si1 C9 108.8(4) . . ?
C3 Si1 C9 117.7(4) . . ?
C13 Si2 C20 107.67(19) . . ?
C13 Si2 C14 109.96(18) . . ?
C20 Si2 C14 114.2(2) . . ?
C13 Si2 C17 104.33(18) . . ?
C20 Si2 C17 111.3(2) . . ?
C14 Si2 C17 108.90(19) . . ?
C33 N1 C23 117.4(3) . . ?
C32 N2 C38 117.6(3) . . ?
C2 C1 C24 178.5(4) . . ?
C1 C2 Si1 177.5(4) . . ?
C5 C3 C4 115.4(7) . . ?
C5 C3 Si1 120.5(5) . . ?
C4 C3 Si1 113.5(5) . . ?
C8 C6 C7 101.1(7) . . ?
C8 C6 Si1 114.5(6) . . ?
C7 C6 Si1 115.4(5) . . ?
C10 C9 C11 115.8(8) . . ?
C10 C9 Si1 120.1(7) . . ?
C11 C9 Si1 111.1(7) . . ?
C13 C12 C31 176.2(4) . . ?
C12 C13 Si2 168.4(4) . . ?
C15 C14 C16 109.5(4) . . ?
C15 C14 Si2 113.6(3) . . ?
C16 C14 Si2 112.8(3) . . ?
C18 C17 C19 110.7(4) . . ?
C18 C17 Si2 114.2(3) . . ?
C19 C17 Si2 112.7(3) . . ?
C21 C20 C22 111.7(5) . . ?
C21 C20 Si2 116.9(4) . . ?
C22 C20 Si2 113.8(3) . . ?
N1 C23 C24 119.7(3) . . ?
N1 C23 C32 120.7(3) . . ?
C24 C23 C32 119.5(3) . . ?
C25 C24 C23 120.3(3) . . ?
C25 C24 C1 120.6(3) . . ?
C23 C24 C1 119.0(3) . . ?
C24 C25 C26 122.6(3) . . ?
C24 C25 C30 120.3(3) . . ?
C26 C25 C30 117.1(3) . . ?
C27 C26 C25 122.1(3) . . ?
C26 C27 C28 120.6(4) . . ?
C29 C28 C27 119.7(4) . . ?
C28 C29 C30 122.1(4) . . ?
C31 C30 C29 121.9(3) . . ?
C31 C30 C25 119.7(3) . . ?
C29 C30 C25 118.4(3) . . ?
C30 C31 C32 120.5(3) . . ?
C30 C31 C12 122.1(3) . . ?
C32 C31 C12 117.4(3) . . ?
N2 C32 C31 119.2(3) . . ?
N2 C32 C23 121.2(3) . . ?
C31 C32 C23 119.6(3) . . ?
N1 C33 C34 119.7(3) . . ?
N1 C33 C38 122.0(3) . . ?
C34 C33 C38 118.3(4) . . ?
C35 C34 C33 120.6(4) . . ?
C35 C34 Cl1 121.5(3) . . ?
C33 C34 Cl1 117.9(3) . . ?
C34 C35 C36 120.7(4) . . ?
C34 C35 Cl2 120.9(3) . . ?
C36 C35 Cl2 118.4(3) . . ?
C37 C36 C35 120.8(4) . . ?
C37 C36 Cl3 120.5(3) . . ?
C35 C36 Cl3 118.7(3) . . ?
C36 C37 C38 120.9(4) . . ?
C36 C37 Cl4 121.5(3) . . ?
C38 C37 Cl4 117.5(3) . . ?
N2 C38 C37 120.3(3) . . ?
N2 C38 C33 121.0(3) . . ?
C37 C38 C33 118.6(4) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 1008544'
