#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/74/1507425.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1507425
loop_
_publ_author_name
'Anthony, John E.'
'Eaton, David L.'
'Parkin, Sean R.'
_publ_section_title
;
 A Road Map to Stable, Soluble, Easily Crystallized Pentacene Derivatives
;
_journal_issue                   1
_journal_name_full               'Organic Letters'
_journal_page_first              15
_journal_paper_doi               10.1021/ol0167356
_journal_volume                  4
_journal_year                    2002
_chemical_formula_sum            'C32 H30 Si2'
_chemical_formula_weight         470.74
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                76.25(3)
_cell_angle_beta                 76.93(3)
_cell_angle_gamma                84.99(3)
_cell_formula_units_Z            1
_cell_length_a                   5.8330(12)
_cell_length_b                   10.146(2)
_cell_length_c                   11.642(2)
_cell_measurement_reflns_used    23355
_cell_measurement_temperature    145(1)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      1.00
_cell_volume                     651.5(2)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material
'SHELX97-2 (Sheldrick, 1997) and local procedures'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      145(1)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0523
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4547
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.84
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'deep blue'
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             250
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         .232
_refine_diff_density_min         -.249
_refine_diff_density_rms         .043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2282
_refine_ls_number_restraints     127
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0291P)²+0.3209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1019
_reflns_number_gt                2012
_reflns_number_total             2282
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0167356_s2.cif
_cod_data_source_block           k01071
_cod_database_code               1507425
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Si Si 0.09845(10) 0.76491(5) 0.88104(5) 0.02281(18) Uani 1 1 d U
C1 C -0.0040(3) 0.57069(18) 0.59247(16) 0.0202(4) Uani 1 1 d U
C2 C 0.1594(3) 0.45983(18) 0.57962(16) 0.0197(4) Uani 1 1 d U
C3 C 0.3194(3) 0.41787(18) 0.65646(16) 0.0221(4) Uani 1 1 d U
H3 H 0.3175 0.4647 0.7183 0.027 Uiso 1 1 calc R
C4 C 0.4798(3) 0.31024(18) 0.64467(16) 0.0213(4) Uani 1 1 d U
C5 C 0.6447(3) 0.2694(2) 0.72186(17) 0.0262(5) Uani 1 1 d U
H5 H 0.6443 0.3163 0.7835 0.031 Uiso 1 1 calc R
C6 C 0.8016(3) 0.1645(2) 0.70810(18) 0.0280(5) Uani 1 1 d U
H6 H 0.9097 0.1386 0.7602 0.034 Uiso 1 1 calc R
C7 C 0.8057(3) 0.09292(19) 0.61629(18) 0.0266(5) Uani 1 1 d U
H7 H 0.9153 0.0190 0.6083 0.032 Uiso 1 1 calc R
C8 C 0.6553(3) 0.12902(18) 0.54033(17) 0.0237(4) Uani 1 1 d U
H8 H 0.6622 0.0808 0.4789 0.028 Uiso 1 1 calc R
C9 C 0.4854(3) 0.23890(18) 0.55102(16) 0.0206(4) Uani 1 1 d U
C10 C 0.3283(3) 0.27906(18) 0.47494(17) 0.0218(4) Uani 1 1 d U
H10 H 0.3313 0.2314 0.4135 0.026 Uiso 1 1 calc R
C11 C 0.1638(3) 0.38845(18) 0.48572(16) 0.0199(4) Uani 1 1 d U
C12 C -0.0016(3) 0.64029(18) 0.68550(17) 0.0208(4) Uani 1 1 d U
C13 C 0.0170(3) 0.69470(18) 0.76445(17) 0.0226(4) Uani 1 1 d U
C14 C 0.3009(4) 0.9054(2) 0.80478(19) 0.0295(5) Uani 1 1 d U
H14A H 0.4499 0.8687 0.7639 0.044 Uiso 1 1 calc R
H14B H 0.3309 0.9510 0.8650 0.044 Uiso 1 1 calc R
H14C H 0.2292 0.9706 0.7451 0.044 Uiso 1 1 calc R
C15 C 0.2599(5) 0.6274(2) 0.9709(2) 0.0518(7) Uani 1 1 d U
H15A H 0.1528 0.5541 1.0150 0.078 Uiso 1 1 calc R
H15B H 0.3207 0.6636 1.0286 0.078 Uiso 1 1 calc R
H15C H 0.3914 0.5918 0.9165 0.078 Uiso 1 1 calc R
C16 C -0.1683(4) 0.8243(3) 0.9785(2) 0.0476(7) Uani 1 1 d U
H16A H -0.2495 0.8973 0.9293 0.071 Uiso 1 1 calc R
H16B H -0.1227 0.8584 1.0419 0.071 Uiso 1 1 calc R
H16C H -0.2739 0.7486 1.0159 0.071 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si .0817 .0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C13 Si C14 108.47(9) . .
C13 Si C16 110.42(10) . .
C14 Si C16 111.27(11) . .
C13 Si C15 107.04(10) . .
C14 Si C15 108.51(11) . .
C16 Si C15 110.99(13) . .
C11 C1 C2 120.68(17) 2_566 .
C11 C1 C12 120.93(17) 2_566 .
C2 C1 C12 118.39(17) . .
C3 C2 C1 121.45(17) . .
C3 C2 C11 118.68(17) . .
C1 C2 C11 119.86(17) . .
C4 C3 C2 122.00(17) . .
C4 C3 H3 119.0 . .
C2 C3 H3 119.0 . .
C3 C4 C5 121.75(17) . .
C3 C4 C9 119.55(17) . .
C5 C4 C9 118.68(17) . .
C6 C5 C4 120.81(18) . .
C6 C5 H5 119.6 . .
C4 C5 H5 119.6 . .
C5 C6 C7 120.57(18) . .
C5 C6 H6 119.7 . .
C7 C6 H6 119.7 . .
C8 C7 C6 120.68(18) . .
C8 C7 H7 119.7 . .
C6 C7 H7 119.7 . .
C7 C8 C9 121.08(18) . .
C7 C8 H8 119.5 . .
C9 C8 H8 119.5 . .
C10 C9 C8 122.84(17) . .
C10 C9 C4 118.99(17) . .
C8 C9 C4 118.17(17) . .
C9 C10 C11 122.17(17) . .
C9 C10 H10 118.9 . .
C11 C10 H10 118.9 . .
C10 C11 C1 121.94(17) . 2_566
C10 C11 C2 118.60(17) . .
C1 C11 C2 119.46(17) 2_566 .
C13 C12 C1 175.1(2) . .
C12 C13 Si 169.94(17) . .
Si C14 H14A 109.5 . .
Si C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
Si C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
Si C15 H15A 109.5 . .
Si C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
Si C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
Si C16 H16A 109.5 . .
Si C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
Si C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Si C13 1.8400(19) .
Si C14 1.853(2) .
Si C16 1.854(2) .
Si C15 1.857(2) .
C1 C11 1.416(3) 2_566
C1 C2 1.423(3) .
C1 C12 1.430(3) .
C2 C3 1.407(3) .
C2 C11 1.442(3) .
C3 C4 1.386(3) .
C3 H3 0.9500 .
C4 C5 1.431(3) .
C4 C9 1.438(3) .
C5 C6 1.357(3) .
C5 H5 0.9500 .
C6 C7 1.423(3) .
C6 H6 0.9500 .
C7 C8 1.352(3) .
C7 H7 0.9500 .
C8 C9 1.435(3) .
C8 H8 0.9500 .
C9 C10 1.386(3) .
C10 C11 1.412(3) .
C10 H10 0.9500 .
C11 C1 1.416(3) 2_566
C12 C13 1.208(3) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
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_4
C11 C1 C2 C3 179.98(16) 2_566 .
C12 C1 C2 C3 0.5(3) . .
C11 C1 C2 C11 0.3(3) 2_566 .
C12 C1 C2 C11 -179.20(16) . .
C1 C2 C3 C4 -179.84(16) . .
C11 C2 C3 C4 -0.2(3) . .
C2 C3 C4 C5 178.99(16) . .
C2 C3 C4 C9 0.3(3) . .
C3 C4 C5 C6 -179.42(18) . .
C9 C4 C5 C6 -0.7(3) . .
C4 C5 C6 C7 0.1(3) . .
C5 C6 C7 C8 0.7(3) . .
C6 C7 C8 C9 -0.9(3) . .
C7 C8 C9 C10 179.96(17) . .
C7 C8 C9 C4 0.2(3) . .
C3 C4 C9 C10 -0.5(3) . .
C5 C4 C9 C10 -179.16(16) . .
C3 C4 C9 C8 179.28(16) . .
C5 C4 C9 C8 0.6(2) . .
C8 C9 C10 C11 -179.26(16) . .
C4 C9 C10 C11 0.5(3) . .
C9 C10 C11 C1 179.83(16) . 2_566
C9 C10 C11 C2 -0.3(3) . .
C3 C2 C11 C10 0.2(3) . .
C1 C2 C11 C10 179.84(16) . .
C3 C2 C11 C1 -179.98(16) . 2_566
C1 C2 C11 C1 -0.3(3) . 2_566
C11 C1 C12 C13 -162(2) 2_566 .
C2 C1 C12 C13 17(2) . .
C1 C12 C13 Si 6(3) . .
C14 Si C13 C12 72.7(10) . .
C16 Si C13 C12 -165.2(9) . .
C15 Si C13 C12 -44.2(10) . .
