#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/65/1506596.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_1506596
loop_
_publ_author_name
'Swartz, Christopher R.'
'Parkin, Sean R.'
'Bullock, Joseph E.'
'Anthony, John E.'
'Mayer, Alex C.'
'Malliaras, George G.'
_publ_section_title
;
 Synthesis and characterization of electron-deficient pentacenes.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3163
_journal_page_last               3166
_journal_paper_doi               10.1021/ol050872b
_journal_volume                  7
_journal_year                    2005
_chemical_formula_moiety         'C48 H50 N4 Si2'
_chemical_formula_sum            'C48 H50 N4 Si2'
_chemical_formula_weight         739.10
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.9757(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.6777(6)
_cell_length_b                   7.3590(2)
_cell_length_c                   22.1035(6)
_cell_measurement_reflns_used    5002
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     4136.32(19)
_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 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      90.0(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full .999
_diffrn_measured_fraction_theta_max .999
_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  0.0567
_diffrn_reflns_av_sigmaI/netI    0.0864
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8102
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_correction_T_min  0.9463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1576
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_refine_diff_density_max         .310
_refine_diff_density_min         -.297
_refine_diff_density_rms         .061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4757
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1084
_refine_ls_R_factor_gt           0.0506
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0568P)²+0.4913P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1235
_reflns_number_gt                2894
_reflns_number_total             4757
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol050872bsi20050609_051818.cif
_cod_data_source_block           k04040
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1506596
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'
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
Si1 Si 0.07390(2) 0.87459(8) 0.14073(2) 0.01660(16) Uani 1 1 d .
C1 C 0.20931(7) 0.7733(3) 0.03690(8) 0.0144(4) Uani 1 1 d .
C2 C 0.24132(7) 0.6166(3) 0.04449(8) 0.0149(4) Uani 1 1 d .
C3 C 0.23415(7) 0.4827(3) 0.08838(8) 0.0163(4) Uani 1 1 d .
H3 H 0.2079 0.5002 0.1142 0.020 Uiso 1 1 calc R
C4 C 0.26459(7) 0.3262(3) 0.09471(8) 0.0156(5) Uani 1 1 d .
C5 C 0.25711(7) 0.1880(3) 0.13807(9) 0.0179(5) Uani 1 1 d .
H5 H 0.2310 0.2038 0.1641 0.021 Uiso 1 1 calc R
C6 C 0.28676(7) 0.0342(3) 0.14278(9) 0.0176(5) Uani 1 1 d .
C7 C 0.32724(7) 0.0087(3) 0.10435(8) 0.0172(5) Uani 1 1 d .
C8 C 0.33572(7) 0.1388(3) 0.06286(8) 0.0166(4) Uani 1 1 d .
H8 H 0.3625 0.1210 0.0378 0.020 Uiso 1 1 calc R
C9 C 0.30514(7) 0.3009(3) 0.05642(9) 0.0152(4) Uani 1 1 d .
C10 C 0.31332(7) 0.4337(3) 0.01427(8) 0.0165(4) Uani 1 1 d .
H10 H 0.3406 0.4173 -0.0103 0.020 Uiso 1 1 calc R
C11 C 0.28242(7) 0.5921(3) 0.00677(8) 0.0148(4) Uani 1 1 d .
C12 C 0.16745(7) 0.7978(3) 0.07283(9) 0.0166(4) Uani 1 1 d .
C13 C 0.13140(8) 0.8233(3) 0.10166(9) 0.0189(5) Uani 1 1 d .
C14 C 0.05707(8) 1.1207(3) 0.12498(9) 0.0216(5) Uani 1 1 d .
H14 H 0.0367 1.1266 0.0830 0.026 Uiso 1 1 calc R
C15 C 0.10576(8) 1.2437(3) 0.12472(11) 0.0286(5) Uani 1 1 d .
H15A H 0.0944 1.3659 0.1110 0.043 Uiso 1 1 calc R
H15B H 0.1286 1.1930 0.0969 0.043 Uiso 1 1 calc R
H15C H 0.1252 1.2503 0.1661 0.043 Uiso 1 1 calc R
C16 C 0.02086(8) 1.1942(3) 0.16919(11) 0.0305(6) Uani 1 1 d .
H16A H 0.0401 1.1978 0.2107 0.046 Uiso 1 1 calc R
H16B H -0.0098 1.1146 0.1684 0.046 Uiso 1 1 calc R
H16C H 0.0092 1.3171 0.1567 0.046 Uiso 1 1 calc R
C17 C 0.02023(7) 0.7179(3) 0.10507(9) 0.0193(5) Uani 1 1 d .
H17 H 0.0359 0.5933 0.1069 0.023 Uiso 1 1 calc R
C18 C 0.00196(9) 0.7563(3) 0.03728(10) 0.0323(6) Uani 1 1 d .
H18A H -0.0216 0.6589 0.0201 0.048 Uiso 1 1 calc R
H18B H 0.0326 0.7618 0.0154 0.048 Uiso 1 1 calc R
H18C H -0.0168 0.8726 0.0331 0.048 Uiso 1 1 calc R
C19 C -0.02733(8) 0.7070(3) 0.13974(10) 0.0278(5) Uani 1 1 d .
H19A H -0.0462 0.8231 0.1361 0.042 Uiso 1 1 calc R
H19B H -0.0153 0.6813 0.1829 0.042 Uiso 1 1 calc R
H19C H -0.0509 0.6097 0.1224 0.042 Uiso 1 1 calc R
C20 C 0.09103(8) 0.8248(3) 0.22445(9) 0.0198(5) Uani 1 1 d .
H20 H 0.0590 0.8520 0.2440 0.024 Uiso 1 1 calc R
C21 C 0.10401(8) 0.6240(3) 0.23616(9) 0.0260(5) Uani 1 1 d .
H21A H 0.1361 0.5931 0.2190 0.039 Uiso 1 1 calc R
H21B H 0.0748 0.5491 0.2168 0.039 Uiso 1 1 calc R
H21C H 0.1095 0.6009 0.2803 0.039 Uiso 1 1 calc R
C22 C 0.13576(8) 0.9428(3) 0.25673(10) 0.0303(6) Uani 1 1 d .
H22A H 0.1416 0.9130 0.3004 0.045 Uiso 1 1 calc R
H22B H 0.1263 1.0713 0.2515 0.045 Uiso 1 1 calc R
H22C H 0.1680 0.9192 0.2390 0.045 Uiso 1 1 calc R
C23 C 0.27883(7) -0.1043(3) 0.18703(9) 0.0205(5) Uani 1 1 d .
N1 N 0.27296(7) -0.2132(3) 0.22173(9) 0.0294(5) Uani 1 1 d .
C24 C 0.35916(8) -0.1534(3) 0.10982(9) 0.0202(5) Uani 1 1 d .
N2 N 0.38479(7) -0.2817(3) 0.11388(8) 0.0288(5) Uani 1 1 d .
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'
N N .0061 .0033 '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 Si1 C20 109.10(9) . .
C13 Si1 C14 106.72(9) . .
C20 Si1 C14 112.71(9) . .
C13 Si1 C17 105.35(9) . .
C20 Si1 C17 110.53(9) . .
C14 Si1 C17 112.06(9) . .
C2 C1 C11 120.72(16) . 7_565
C2 C1 C12 120.36(17) . .
C11 C1 C12 118.91(17) 7_565 .
C3 C2 C1 121.46(17) . .
C3 C2 C11 119.00(18) . .
C1 C2 C11 119.54(17) . .
C4 C3 C2 121.51(17) . .
C4 C3 H3 119.2 . .
C2 C3 H3 119.2 . .
C3 C4 C5 122.15(18) . .
C3 C4 C9 119.36(17) . .
C5 C4 C9 118.49(17) . .
C6 C5 C4 121.19(18) . .
C6 C5 H5 119.4 . .
C4 C5 H5 119.4 . .
C5 C6 C7 120.29(18) . .
C5 C6 C23 120.56(18) . .
C7 C6 C23 119.14(18) . .
C8 C7 C6 120.00(18) . .
C8 C7 C24 119.65(18) . .
C6 C7 C24 120.35(17) . .
C7 C8 C9 121.17(18) . .
C7 C8 H8 119.4 . .
C9 C8 H8 119.4 . .
C10 C9 C8 121.65(18) . .
C10 C9 C4 119.50(17) . .
C8 C9 C4 118.84(17) . .
C9 C10 C11 121.85(17) . .
C9 C10 H10 119.1 . .
C11 C10 H10 119.1 . .
C10 C11 C1 121.53(17) . 7_565
C10 C11 C2 118.73(17) . .
C1 C11 C2 119.74(17) 7_565 .
C13 C12 C1 177.6(2) . .
C12 C13 Si1 175.35(18) . .
C16 C14 C15 110.96(18) . .
C16 C14 Si1 111.36(14) . .
C15 C14 Si1 113.52(14) . .
C16 C14 H14 106.9 . .
C15 C14 H14 106.9 . .
Si1 C14 H14 106.9 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C14 C16 H16A 109.5 . .
C14 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C14 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C19 C17 C18 109.98(16) . .
C19 C17 Si1 114.23(14) . .
C18 C17 Si1 113.77(15) . .
C19 C17 H17 106.0 . .
C18 C17 H17 106.0 . .
Si1 C17 H17 106.0 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C17 C19 H19A 109.5 . .
C17 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C17 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C21 C20 C22 109.66(17) . .
C21 C20 Si1 111.78(14) . .
C22 C20 Si1 113.94(14) . .
C21 C20 H20 107.0 . .
C22 C20 H20 107.0 . .
Si1 C20 H20 107.0 . .
C20 C21 H21A 109.5 . .
C20 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C20 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C20 C22 H22A 109.5 . .
C20 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C20 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
N1 C23 C6 179.5(2) . .
N2 C24 C7 179.5(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Si1 C13 1.850(2) .
Si1 C20 1.878(2) .
Si1 C14 1.883(2) .
Si1 C17 1.884(2) .
C1 C2 1.413(3) .
C1 C11 1.419(3) 7_565
C1 C12 1.434(3) .
C2 C3 1.413(3) .
C2 C11 1.444(2) .
C3 C4 1.388(3) .
C3 H3 0.9500 .
C4 C5 1.429(3) .
C4 C9 1.442(3) .
C5 C6 1.360(3) .
C5 H5 0.9500 .
C6 C7 1.443(3) .
C6 C23 1.447(3) .
C7 C8 1.364(3) .
C7 C24 1.443(3) .
C8 C9 1.424(3) .
C8 H8 0.9500 .
C9 C10 1.386(3) .
C10 C11 1.407(3) .
C10 H10 0.9500 .
C11 C1 1.419(3) 7_565
C12 C13 1.209(3) .
C14 C16 1.537(3) .
C14 C15 1.544(3) .
C14 H14 1.0000 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 C19 1.531(3) .
C17 C18 1.533(3) .
C17 H17 1.0000 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 C21 1.529(3) .
C20 C22 1.534(3) .
C20 H20 1.0000 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 N1 1.133(2) .
C24 N2 1.147(3) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C11 C1 C2 C3 179.01(18) 7_565 .
C12 C1 C2 C3 -1.7(3) . .
C11 C1 C2 C11 -0.8(3) 7_565 .
C12 C1 C2 C11 178.42(17) . .
C1 C2 C3 C4 178.16(17) . .
C11 C2 C3 C4 -2.0(3) . .
C2 C3 C4 C5 -178.75(18) . .
C2 C3 C4 C9 1.2(3) . .
C3 C4 C5 C6 178.82(18) . .
C9 C4 C5 C6 -1.1(3) . .
C4 C5 C6 C7 1.0(3) . .
C4 C5 C6 C23 179.82(17) . .
C5 C6 C7 C8 -0.3(3) . .
C23 C6 C7 C8 -179.22(18) . .
C5 C6 C7 C24 179.24(18) . .
C23 C6 C7 C24 0.4(3) . .
C6 C7 C8 C9 -0.1(3) . .
C24 C7 C8 C9 -179.70(17) . .
C7 C8 C9 C10 -179.78(18) . .
C7 C8 C9 C4 0.0(3) . .
C3 C4 C9 C10 0.5(3) . .
C5 C4 C9 C10 -179.62(17) . .
C3 C4 C9 C8 -179.30(17) . .
C5 C4 C9 C8 0.6(3) . .
C8 C9 C10 C11 178.52(17) . .
C4 C9 C10 C11 -1.2(3) . .
C9 C10 C11 C1 -179.37(18) . 7_565
C9 C10 C11 C2 0.4(3) . .
C3 C2 C11 C10 1.2(3) . .
C1 C2 C11 C10 -178.94(16) . .
C3 C2 C11 C1 -179.03(17) . 7_565
C1 C2 C11 C1 0.8(3) . 7_565
C13 Si1 C14 C16 -163.66(14) . .
C20 Si1 C14 C16 -43.92(17) . .
C17 Si1 C14 C16 81.51(16) . .
C13 Si1 C14 C15 -37.57(17) . .
C20 Si1 C14 C15 82.17(16) . .
C17 Si1 C14 C15 -152.40(15) . .
C13 Si1 C17 C19 167.33(15) . .
C20 Si1 C17 C19 49.62(17) . .
C14 Si1 C17 C19 -77.00(17) . .
C13 Si1 C17 C18 -65.25(17) . .
C20 Si1 C17 C18 177.04(15) . .
C14 Si1 C17 C18 50.42(18) . .
C13 Si1 C20 C21 -62.21(16) . .
C14 Si1 C20 C21 179.44(13) . .
C17 Si1 C20 C21 53.18(16) . .
C13 Si1 C20 C22 62.80(17) . .
C14 Si1 C20 C22 -55.55(17) . .
C17 Si1 C20 C22 178.19(14) . .
