#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/54/1515429.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_1515429
loop_
_publ_author_name
'Shu, Ying'
'Lim, Yee-Fun'
'Li, Zhong'
'Purushothaman, Balaji'
'Hallani, Rawad'
'Kim, Jo Eun'
'Parkin, Sean R.'
'Malliaras, George G.'
'Anthony, John E.'
_publ_section_title
;
 A survey of electron-deficient pentacenes as acceptors in polymer bulk
 heterojunction solar cells
;
_journal_issue                   2
_journal_name_full               'Chemical Science'
_journal_page_first              363
_journal_paper_doi               10.1039/c0sc00433b
_journal_volume                  2
_journal_year                    2011
_chemical_formula_moiety         'C44 H53 N O2 Si2'
_chemical_formula_sum            'C44 H53 N O2 Si2'
_chemical_formula_weight         684.05
_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                96.230(1)
_cell_angle_beta                 100.619(1)
_cell_angle_gamma                94.648(1)
_cell_formula_units_Z            1
_cell_length_a                   7.3935(2)
_cell_length_b                   7.7475(2)
_cell_length_c                   17.3713(4)
_cell_measurement_reflns_used    6169
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      68.48
_cell_measurement_theta_min      2.61
_cell_volume                     967.02(4)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker-AXS, 2006)'
_computing_data_reduction        APEX2
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELX-97 (Sheldrick, 2008) and local procedures
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker X8 Proteum diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'graded multilayer optics'
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13133
_diffrn_reflns_theta_full        68.48
_diffrn_reflns_theta_max         68.48
_diffrn_reflns_theta_min         2.61
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.108
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs in APEX2 (BrukerAXS, 2006)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3491
_refine_ls_number_restraints     57
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0736
_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)+(0.0646P)²+2.1061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1900
_refine_ls_wR_factor_ref         0.1962
_reflns_number_gt                3049
_reflns_number_total             3491
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c0sc00433b.txt
_cod_data_source_block           x09015
_cod_database_code               1515429
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.23629(12) 0.67094(13) 0.17917(5) 0.0319(3) Uani 1 1 d . . .
C1 C 0.4420(4) 0.5326(4) 0.42046(18) 0.0276(7) Uani 1 1 d . . .
C2 C 0.3398(4) 0.5882(4) 0.47851(18) 0.0267(6) Uani 1 1 d . . .
C3 C 0.1795(4) 0.6718(4) 0.45902(19) 0.0293(7) Uani 1 1 d . . .
H3 H 0.1403 0.6930 0.4060 0.035 Uiso 1 1 calc R . .
C4 C 0.0755(4) 0.7249(4) 0.5149(2) 0.0311(7) Uani 1 1 d . . .
C5 C -0.0904(5) 0.8046(4) 0.4940(2) 0.0353(8) Uani 1 1 d U A .
H5 H -0.1325 0.8240 0.4409 0.042 Uiso 1 1 calc R . .
C6 C -0.1888(5) 0.8531(4) 0.5504(2) 0.0382(8) Uani 1 1 d DU . .
H6 H -0.3010 0.9035 0.5355 0.046 Uiso 0.564(3) 1 calc PR A 2
N1 N -0.3529(8) 0.9336(8) 0.5257(4) 0.0310(13) Uani 0.436(3) 1 d PDU A 1
O1 O -0.4050(7) 0.9488(7) 0.4551(3) 0.0369(13) Uani 0.436(3) 1 d PDU . 1
O2 O -0.4374(7) 0.9842(7) 0.5783(4) 0.0380(13) Uani 0.436(3) 1 d PDU . 1
C7 C -0.1284(5) 0.8306(5) 0.6302(2) 0.0405(8) Uani 1 1 d DU A .
H7 H -0.1984 0.8679 0.6685 0.049 Uiso 0.936(3) 1 calc PR B 1
N1' N -0.285(4) 0.872(6) 0.6620(19) 0.049(5) Uiso 0.064(3) 1 d PDU A 2
O1' O -0.389(4) 0.974(5) 0.631(2) 0.053(8) Uiso 0.064(3) 1 d PDU A 2
O2' O -0.277(7) 0.837(8) 0.731(2) 0.087(14) Uiso 0.064(3) 1 d PDU A 2
C8 C 0.0293(5) 0.7556(5) 0.6524(2) 0.0385(8) Uani 1 1 d U . .
H8 H 0.0686 0.7403 0.7062 0.046 Uiso 1 1 calc R A .
C9 C 0.1378(5) 0.6989(4) 0.5955(2) 0.0320(7) Uani 1 1 d . A .
C10 C 0.2967(4) 0.6176(4) 0.61583(19) 0.0313(7) Uani 1 1 d . . .
H10 H 0.3377 0.6008 0.6694 0.038 Uiso 1 1 calc R A .
C11 C 0.3992(4) 0.5591(4) 0.55912(18) 0.0271(7) Uani 1 1 d . . .
C12 C 0.3834(4) 0.5665(4) 0.34152(19) 0.0295(7) Uani 1 1 d . . .
C13 C 0.3293(4) 0.6003(5) 0.27515(19) 0.0334(7) Uani 1 1 d . . .
C14 C 0.1953(5) 0.4727(5) 0.1027(2) 0.0392(8) Uani 1 1 d . . .
H14 H 0.1424 0.5110 0.0508 0.047 Uiso 1 1 calc R . .
C15 C 0.0558(6) 0.3309(6) 0.1194(3) 0.0524(10) Uani 1 1 d . . .
H15A H 0.0402 0.2306 0.0784 0.079 Uiso 1 1 calc R . .
H15B H -0.0635 0.3776 0.1194 0.079 Uiso 1 1 calc R . .
H15C H 0.1014 0.2940 0.1710 0.079 Uiso 1 1 calc R . .
C16 C 0.3769(6) 0.3985(5) 0.0945(2) 0.0451(9) Uani 1 1 d . . .
H16A H 0.4374 0.3683 0.1457 0.068 Uiso 1 1 calc R . .
H16B H 0.4583 0.4859 0.0769 0.068 Uiso 1 1 calc R . .
H16C H 0.3516 0.2936 0.0557 0.068 Uiso 1 1 calc R . .
C17 C 0.4207(5) 0.8303(5) 0.1573(2) 0.0369(8) Uani 1 1 d . . .
H17 H 0.5345 0.7677 0.1607 0.044 Uiso 1 1 calc R . .
C18 C 0.3815(5) 0.8821(6) 0.0738(2) 0.0444(9) Uani 1 1 d . . .
H18A H 0.2799 0.9565 0.0690 0.067 Uiso 1 1 calc R . .
H18B H 0.3467 0.7769 0.0354 0.067 Uiso 1 1 calc R . .
H18C H 0.4926 0.9463 0.0636 0.067 Uiso 1 1 calc R . .
C19 C 0.4717(6) 0.9907(5) 0.2191(2) 0.0476(9) Uani 1 1 d . . .
H19A H 0.5831 1.0572 0.2105 0.071 Uiso 1 1 calc R . .
H19B H 0.4954 0.9537 0.2719 0.071 Uiso 1 1 calc R . .
H19C H 0.3694 1.0642 0.2147 0.071 Uiso 1 1 calc R . .
C20 C 0.0201(5) 0.7782(6) 0.1904(2) 0.0471(9) Uani 1 1 d . . .
H20 H 0.0624 0.8958 0.2211 0.056 Uiso 1 1 calc R . .
C21 C -0.0933(5) 0.8099(6) 0.1110(3) 0.0522(11) Uani 1 1 d . . .
H21A H -0.1440 0.6976 0.0799 0.078 Uiso 1 1 calc R . .
H21B H -0.0136 0.8741 0.0822 0.078 Uiso 1 1 calc R . .
H21C H -0.1949 0.8783 0.1202 0.078 Uiso 1 1 calc R . .
C22 C -0.1048(6) 0.6821(8) 0.2374(3) 0.0709(16) Uani 1 1 d . . .
H22A H -0.1858 0.7629 0.2574 0.106 Uiso 1 1 calc R . .
H22B H -0.0278 0.6385 0.2818 0.106 Uiso 1 1 calc R . .
H22C H -0.1804 0.5838 0.2028 0.106 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 '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 C17 106.72(15) . .
C13 Si1 C14 107.62(16) . .
C17 Si1 C14 109.35(16) . .
C13 Si1 C20 107.01(16) . .
C17 Si1 C20 111.61(18) . .
C14 Si1 C20 114.15(17) . .
C2 C1 C12 119.3(3) . .
C2 C1 C11 120.4(3) . 2_666
C12 C1 C11 120.3(3) . 2_666
C3 C2 C1 121.3(3) . .
C3 C2 C11 118.5(3) . .
C1 C2 C11 120.2(3) . .
C4 C3 C2 122.1(3) . .
C4 C3 H3 118.9 . .
C2 C3 H3 118.9 . .
C3 C4 C5 121.7(3) . .
C3 C4 C9 119.1(3) . .
C5 C4 C9 119.2(3) . .
C6 C5 C4 119.8(3) . .
C6 C5 H5 120.1 . .
C4 C5 H5 120.1 . .
C5 C6 C7 121.7(3) . .
C5 C6 N1 117.1(4) . .
C7 C6 N1 121.1(4) . .
C5 C6 H6 119.1 . .
C7 C6 H6 119.1 . .
N1 C6 H6 2.8 . .
O1 N1 O2 123.6(6) . .
O1 N1 C6 119.9(5) . .
O2 N1 C6 116.5(6) . .
N1 O1 O2 127.1(5) . 2_476
N1 O2 O1 109.3(6) . 2_476
C8 C7 C6 120.1(3) . .
C8 C7 N1' 137.9(12) . .
C6 C7 N1' 100.9(13) . .
C8 C7 H7 120.0 . .
C6 C7 H7 120.0 . .
N1' C7 H7 21.3 . .
O1' N1' O2' 124.4(19) . .
O1' N1' C7 119.7(17) . .
O2' N1' C7 113.3(16) . .
C7 C8 C9 120.9(3) . .
C7 C8 H8 119.6 . .
C9 C8 H8 119.6 . .
C10 C9 C4 119.4(3) . .
C10 C9 C8 122.3(3) . .
C4 C9 C8 118.2(3) . .
C9 C10 C11 121.7(3) . .
C9 C10 H10 119.2 . .
C11 C10 H10 119.2 . .
C10 C11 C1 121.5(3) . 2_666
C10 C11 C2 119.2(3) . .
C1 C11 C2 119.3(3) 2_666 .
C13 C12 C1 177.5(4) . .
C12 C13 Si1 173.9(3) . .
C16 C14 C15 110.5(3) . .
C16 C14 Si1 111.0(3) . .
C15 C14 Si1 112.6(3) . .
C16 C14 H14 107.5 . .
C15 C14 H14 107.5 . .
Si1 C14 H14 107.5 . .
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 111.2(3) . .
C19 C17 Si1 113.1(2) . .
C18 C17 Si1 114.4(3) . .
C19 C17 H17 105.7 . .
C18 C17 H17 105.7 . .
Si1 C17 H17 105.7 . .
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 110.0(3) . .
C21 C20 Si1 112.5(3) . .
C22 C20 Si1 114.3(3) . .
C21 C20 H20 106.5 . .
C22 C20 H20 106.5 . .
Si1 C20 H20 106.5 . .
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 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Si1 C13 1.841(3) .
Si1 C17 1.884(4) .
Si1 C14 1.884(4) .
Si1 C20 1.891(4) .
C1 C2 1.419(4) .
C1 C12 1.420(4) .
C1 C11 1.430(4) 2_666
C2 C3 1.401(4) .
C2 C11 1.436(4) .
C3 C4 1.394(5) .
C3 H3 0.9500 .
C4 C5 1.424(5) .
C4 C9 1.432(5) .
C5 C6 1.362(5) .
C5 H5 0.9500 .
C6 C7 1.410(5) .
C6 N1 1.426(7) .
C6 H6 0.9500 .
N1 O1 1.237(8) .
N1 O2 1.246(8) .
O1 O2 1.371(8) 2_476
O2 O1 1.371(8) 2_476
C7 C8 1.356(5) .
C7 N1' 1.419(12) .
C7 H7 0.9500 .
N1' O1' 1.238(13) .
N1' O2' 1.246(12) .
C8 C9 1.438(5) .
C8 H8 0.9500 .
C9 C10 1.385(5) .
C10 C11 1.408(4) .
C10 H10 0.9500 .
C11 C1 1.430(4) 2_666
C12 C13 1.212(5) .
C14 C16 1.527(5) .
C14 C15 1.533(6) .
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 1.525(5) .
C17 C18 1.528(5) .
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 1.532(5) .
C20 C22 1.540(6) .
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 .
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
C12 C1 C2 C3 1.8(5) . .
C11 C1 C2 C3 -177.3(3) 2_666 .
C12 C1 C2 C11 -178.4(3) . .
C11 C1 C2 C11 2.5(5) 2_666 .
C1 C2 C3 C4 178.9(3) . .
C11 C2 C3 C4 -0.9(5) . .
C2 C3 C4 C5 -177.9(3) . .
C2 C3 C4 C9 2.2(5) . .
C3 C4 C5 C6 179.4(3) . .
C9 C4 C5 C6 -0.8(5) . .
C4 C5 C6 C7 1.6(5) . .
C4 C5 C6 N1 179.5(4) . .
C5 C6 N1 O1 3.5(7) . .
C7 C6 N1 O1 -178.6(5) . .
C5 C6 N1 O2 -177.0(5) . .
C7 C6 N1 O2 0.9(7) . .
O2 N1 O1 O2 -2.4(11) . 2_476
C6 N1 O1 O2 177.1(5) . 2_476
O1 N1 O2 O1 2.0(10) . 2_476
C6 N1 O2 O1 -177.5(5) . 2_476
C5 C6 C7 C8 -1.4(5) . .
N1 C6 C7 C8 -179.2(4) . .
C5 C6 C7 N1' -171(2) . .
N1 C6 C7 N1' 11(2) . .
C8 C7 N1' O1' 166(3) . .
C6 C7 N1' O1' -27(5) . .
C8 C7 N1' O2' 3(6) . .
C6 C7 N1' O2' 170(4) . .
C6 C7 C8 C9 0.3(5) . .
N1' C7 C8 C9 165(3) . .
C3 C4 C9 C10 -1.7(5) . .
C5 C4 C9 C10 178.4(3) . .
C3 C4 C9 C8 179.6(3) . .
C5 C4 C9 C8 -0.2(5) . .
C7 C8 C9 C10 -178.2(3) . .
C7 C8 C9 C4 0.4(5) . .
C4 C9 C10 C11 -0.1(5) . .
C8 C9 C10 C11 178.5(3) . .
C9 C10 C11 C1 -176.8(3) . 2_666
C9 C10 C11 C2 1.5(5) . .
C3 C2 C11 C10 -1.0(4) . .
C1 C2 C11 C10 179.2(3) . .
C3 C2 C11 C1 177.4(3) . 2_666
C1 C2 C11 C1 -2.4(5) . 2_666
C2 C1 C12 C13 17(8) . .
C11 C1 C12 C13 -163(8) 2_666 .
C1 C12 C13 Si1 8(10) . .
C17 Si1 C13 C12 90(3) . .
C14 Si1 C13 C12 -152(3) . .
C20 Si1 C13 C12 -29(3) . .
C13 Si1 C14 C16 -63.9(3) . .
C17 Si1 C14 C16 51.7(3) . .
C20 Si1 C14 C16 177.5(3) . .
C13 Si1 C14 C15 60.7(3) . .
C17 Si1 C14 C15 176.2(3) . .
C20 Si1 C14 C15 -57.9(3) . .
C13 Si1 C17 C19 -60.4(3) . .
C14 Si1 C17 C19 -176.5(3) . .
C20 Si1 C17 C19 56.2(3) . .
C13 Si1 C17 C18 170.8(3) . .
C14 Si1 C17 C18 54.7(3) . .
C20 Si1 C17 C18 -72.6(3) . .
C13 Si1 C20 C21 -168.3(3) . .
C17 Si1 C20 C21 75.3(3) . .
C14 Si1 C20 C21 -49.4(4) . .
C13 Si1 C20 C22 -41.9(4) . .
C17 Si1 C20 C22 -158.3(3) . .
C14 Si1 C20 C22 77.0(3) . .
