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#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/71/1507107.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_1507107
loop_
_publ_author_name
'Payne, Marcia M.'
'Delcamp, Jared H.'
'Parkin, Sean R.'
'Anthony, John E.'
_publ_section_title
;
 Robust, soluble pentacene ethers.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              1609
_journal_page_last               1612
_journal_paper_doi               10.1021/ol049593z
_journal_volume                  6
_journal_year                    2004
_chemical_formula_sum            'C46 H54 O4 Si2'
_chemical_formula_weight         727.07
_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                93.790(10)
_cell_angle_beta                 101.850(10)
_cell_angle_gamma                93.840(10)
_cell_formula_units_Z            1
_cell_length_a                   7.6170(10)
_cell_length_b                   7.7650(10)
_cell_length_c                   17.5390(10)
_cell_measurement_reflns_used    3318
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1009.6(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      90.0(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4340
_diffrn_reflns_theta_full        22.50
_diffrn_reflns_theta_max         22.50
_diffrn_reflns_theta_min         2.38
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_correction_T_min  0.9682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            'very dark'
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             390
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         2625
_refine_ls_number_restraints     92
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1260
_refine_ls_R_factor_gt           0.0605
_refine_ls_shift/su_max          0.314
_refine_ls_shift/su_mean         0.015
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0668P)²+0.3896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1550
_reflns_number_gt                1563
_reflns_number_total             2625
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol049593zsi20040304_025733.cif
_cod_data_source_block           k03069
_cod_original_cell_volume        1009.58(19)
_cod_database_code               1507107
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 0.26683(17) 0.34382(16) 0.32535(7) 0.0375(4) Uani 1 1 d U B .
O1 O 0.8394(4) 0.0826(3) -0.02453(15) 0.0360(7) Uani 1 1 d U . .
O2 O 0.7305(4) 0.1017(4) -0.15692(16) 0.0419(8) Uani 1 1 d U . .
C1 C 0.0622(5) 0.4760(5) 0.0803(2) 0.0274(10) Uani 1 1 d U . .
C2 C 0.1624(5) 0.4214(4) 0.0246(2) 0.0255(9) Uani 1 1 d U . .
C3 C 0.3270(5) 0.3449(5) 0.0472(2) 0.0278(9) Uani 1 1 d U . .
H3 H 0.3719 0.3340 0.1013 0.033 Uiso 1 1 calc R . .
C4 C 0.4249(5) 0.2854(5) -0.0056(2) 0.0268(9) Uani 1 1 d U . .
C5 C 0.5906(5) 0.2112(5) 0.0198(2) 0.0303(10) Uani 1 1 d U . .
H5 H 0.6373 0.2008 0.0737 0.036 Uiso 1 1 calc R . .
C6 C 0.6789(6) 0.1565(5) -0.0349(2) 0.0307(10) Uani 1 1 d U . .
C7 C 0.8719(6) 0.0393(5) -0.1011(2) 0.0377(11) Uani 1 1 d U . .
H7A H 0.9900 0.0940 -0.1057 0.045 Uiso 1 1 calc R . .
H7B H 0.8728 -0.0878 -0.1105 0.045 Uiso 1 1 calc R . .
C8 C 0.6126(6) 0.1682(5) -0.1153(2) 0.0315(10) Uani 1 1 d U . .
C9 C 0.4591(6) 0.2381(5) -0.1439(2) 0.0315(10) Uani 1 1 d U . .
H9 H 0.4184 0.2451 -0.1984 0.038 Uiso 1 1 calc R . .
C10 C 0.3576(5) 0.3024(5) -0.0881(2) 0.0273(9) Uani 1 1 d U . .
C11 C 0.1998(5) 0.3826(5) -0.1109(2) 0.0288(10) Uani 1 1 d U . .
H11 H 0.1580 0.3974 -0.1647 0.035 Uiso 1 1 calc R . .
C12 C 0.0996(5) 0.4430(5) -0.0568(2) 0.0262(9) Uani 1 1 d U . .
C13 C 0.1251(5) 0.4436(5) 0.1608(2) 0.0298(10) Uani 1 1 d U . .
C14 C 0.1783(5) 0.4066(5) 0.2267(2) 0.0324(10) Uani 1 1 d U . .
C15 C 0.0846(6) 0.2025(5) 0.3530(2) 0.0379(10) Uani 1 1 d U . .
H15 H -0.0212 0.2732 0.3501 0.045 Uiso 1 1 calc R . .
C16 C 0.0210(6) 0.0416(5) 0.2949(2) 0.0511(12) Uani 1 1 d U . .
H16A H 0.1222 -0.0293 0.2936 0.077 Uiso 1 1 calc R . .
H16B H -0.0243 0.0786 0.2426 0.077 Uiso 1 1 calc R . .
H16C H -0.0753 -0.0265 0.3116 0.077 Uiso 1 1 calc R . .
C17 C 0.1320(6) 0.1499(6) 0.4372(2) 0.0546(13) Uani 1 1 d U . .
H17A H 0.0264 0.0884 0.4499 0.082 Uiso 1 1 calc R . .
H17B H 0.1692 0.2538 0.4733 0.082 Uiso 1 1 calc R . .
H17C H 0.2307 0.0739 0.4422 0.082 Uiso 1 1 calc R . .
C18 C 0.3148(6) 0.5466(5) 0.3923(2) 0.0421(11) Uani 1 1 d U . .
H18 H 0.3756 0.5147 0.4451 0.051 Uiso 1 1 calc R . .
C19 C 0.1391(6) 0.6260(6) 0.4011(3) 0.0550(13) Uani 1 1 d U . .
H19A H 0.1681 0.7361 0.4334 0.082 Uiso 1 1 calc R . .
H19B H 0.0679 0.5460 0.4261 0.082 Uiso 1 1 calc R . .
H19C H 0.0697 0.6462 0.3494 0.082 Uiso 1 1 calc R . .
C20 C 0.4431(7) 0.6825(6) 0.3658(3) 0.0632(14) Uani 1 1 d U . .
H20A H 0.3880 0.7144 0.3137 0.095 Uiso 1 1 calc R . .
H20B H 0.5576 0.6334 0.3642 0.095 Uiso 1 1 calc R . .
H20C H 0.4647 0.7857 0.4029 0.095 Uiso 1 1 calc R . .
C21 C 0.4706(6) 0.2223(6) 0.3228(2) 0.0472(12) Uani 1 1 d DU . .
H21 H 0.4318 0.1018 0.2988 0.057 Uiso 1 1 calc R A 1
C22 C 0.5940(6) 0.2151(6) 0.4019(2) 0.0554(14) Uani 1 1 d DU B .
H22A H 0.6851 0.1339 0.3974 0.083 Uiso 1 1 calc R . .
H22B H 0.5234 0.1762 0.4393 0.083 Uiso 1 1 calc R . .
H22C H 0.6535 0.3306 0.4202 0.083 Uiso 1 1 calc R . .
C23 C 0.5889(16) 0.321(3) 0.2699(8) 0.058(4) Uani 0.57(3) 1 d PDU B 1
H23A H 0.5148 0.3294 0.2177 0.087 Uiso 0.57(3) 1 calc PR B 1
H23B H 0.6929 0.2565 0.2655 0.087 Uiso 0.57(3) 1 calc PR B 1
H23C H 0.6307 0.4379 0.2944 0.087 Uiso 0.57(3) 1 calc PR B 1
C23' C 0.576(2) 0.234(3) 0.2582(9) 0.044(4) Uani 0.43(3) 1 d PDU B 2
H23D H 0.4929 0.2379 0.2079 0.067 Uiso 0.43(3) 1 calc PR B 2
H23E H 0.6456 0.1323 0.2564 0.067 Uiso 0.43(3) 1 calc PR B 2
H23F H 0.6590 0.3392 0.2688 0.067 Uiso 0.43(3) 1 calc PR B 2
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'
O O 0.0106 0.0060 '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
C14 Si1 C18 107.28(19) . .
C14 Si1 C15 107.08(18) . .
C18 Si1 C15 109.32(19) . .
C14 Si1 C21 108.37(18) . .
C18 Si1 C21 113.6(2) . .
C15 Si1 C21 110.9(2) . .
C6 O1 C7 106.8(3) . .
C8 O2 C7 106.5(3) . .
C2 C1 C12 120.6(3) . 2_565
C2 C1 C13 118.7(4) . .
C12 C1 C13 120.7(3) 2_565 .
C1 C2 C3 121.5(4) . .
C1 C2 C12 120.6(4) . .
C3 C2 C12 117.9(3) . .
C4 C3 C2 123.0(4) . .
C4 C3 H3 118.5 . .
C2 C3 H3 118.5 . .
C3 C4 C5 121.1(4) . .
C3 C4 C10 118.8(4) . .
C5 C4 C10 120.2(3) . .
C6 C5 C4 117.8(4) . .
C6 C5 H5 121.1 . .
C4 C5 H5 121.1 . .
C5 C6 O1 128.2(4) . .
C5 C6 C8 122.6(4) . .
O1 C6 C8 109.2(3) . .
O2 C7 O1 107.7(3) . .
O2 C7 H7A 110.2 . .
O1 C7 H7A 110.2 . .
O2 C7 H7B 110.2 . .
O1 C7 H7B 110.2 . .
H7A C7 H7B 108.5 . .
C9 C8 O2 127.1(4) . .
C9 C8 C6 123.3(4) . .
O2 C8 C6 109.5(4) . .
C8 C9 C10 117.3(4) . .
C8 C9 H9 121.4 . .
C10 C9 H9 121.4 . .
C11 C10 C9 122.2(4) . .
C11 C10 C4 118.9(4) . .
C9 C10 C4 118.9(4) . .
C10 C11 C12 122.2(4) . .
C10 C11 H11 118.9 . .
C12 C11 H11 118.9 . .
C11 C12 C1 122.1(3) . 2_565
C11 C12 C2 119.1(4) . .
C1 C12 C2 118.8(3) 2_565 .
C14 C13 C1 176.2(4) . .
C13 C14 Si1 177.3(4) . .
C17 C15 C16 110.7(3) . .
C17 C15 Si1 113.7(3) . .
C16 C15 Si1 112.8(3) . .
C17 C15 H15 106.4 . .
C16 C15 H15 106.4 . .
Si1 C15 H15 106.4 . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C15 C17 H17A 109.5 . .
C15 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C15 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C19 C18 C20 110.2(4) . .
C19 C18 Si1 111.1(3) . .
C20 C18 Si1 112.5(3) . .
C19 C18 H18 107.6 . .
C20 C18 H18 107.6 . .
Si1 C18 H18 107.6 . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C18 C20 H20A 109.5 . .
C18 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C18 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C22 C21 C23' 111.5(8) . .
C22 C21 C23 106.2(6) . .
C23' C21 C23 25.2(6) . .
C22 C21 Si1 114.3(3) . .
C23' C21 Si1 123.0(8) . .
C23 C21 Si1 108.1(7) . .
C22 C21 H21 109.5 . .
C23' C21 H21 84.5 . .
C23 C21 H21 109.2 . .
Si1 C21 H21 109.5 . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C21 C23 H23A 109.6 . .
C21 C23 H23B 109.6 . .
H23A C23 H23B 109.5 . .
C21 C23 H23C 109.2 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C21 C23' H23D 109.4 . .
C21 C23' H23E 109.7 . .
H23D C23' H23E 109.5 . .
C21 C23' H23F 109.3 . .
H23D C23' H23F 109.5 . .
H23E C23' H23F 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Si1 C14 1.833(4) .
Si1 C18 1.869(4) .
Si1 C15 1.873(4) .
Si1 C21 1.876(4) .
O1 C6 1.369(5) .
O1 C7 1.437(4) .
O2 C8 1.374(4) .
O2 C7 1.433(5) .
C1 C2 1.418(5) .
C1 C12 1.420(5) 2_565
C1 C13 1.438(5) .
C2 C3 1.418(5) .
C2 C12 1.434(5) .
C3 C4 1.380(5) .
C3 H3 0.9500 .
C4 C5 1.422(5) .
C4 C10 1.450(5) .
C5 C6 1.342(5) .
C5 H5 0.9500 .
C6 C8 1.407(5) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C9 1.339(5) .
C9 C10 1.450(5) .
C9 H9 0.9500 .
C10 C11 1.388(5) .
C11 C12 1.411(5) .
C11 H11 0.9500 .
C12 C1 1.420(5) 2_565
C13 C14 1.205(5) .
C15 C17 1.536(5) .
C15 C16 1.543(6) .
C15 H15 1.0000 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 C19 1.542(6) .
C18 C20 1.548(6) .
C18 H18 1.0000 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 C22 1.514(6) .
C21 C23' 1.524(11) .
C21 C23 1.615(11) .
C21 H21 1.0000 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C23' H23D 0.9800 .
C23' H23E 0.9800 .
C23' H23F 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 178.1(3) 2_565 .
C13 C1 C2 C3 -3.5(5) . .
C12 C1 C2 C12 -1.6(6) 2_565 .
C13 C1 C2 C12 176.7(3) . .
C1 C2 C3 C4 177.9(4) . .
C12 C2 C3 C4 -2.3(5) . .
C2 C3 C4 C5 179.2(3) . .
C2 C3 C4 C10 0.3(5) . .
C3 C4 C5 C6 -179.8(4) . .
C10 C4 C5 C6 -0.9(5) . .
C4 C5 C6 O1 179.6(3) . .
C4 C5 C6 C8 -0.7(6) . .
C7 O1 C6 C5 177.2(4) . .
C7 O1 C6 C8 -2.5(4) . .
C8 O2 C7 O1 -4.0(4) . .
C6 O1 C7 O2 4.0(4) . .
C7 O2 C8 C9 -178.8(4) . .
C7 O2 C8 C6 2.5(4) . .
C5 C6 C8 C9 1.6(6) . .
O1 C6 C8 C9 -178.7(4) . .
C5 C6 C8 O2 -179.7(4) . .
O1 C6 C8 O2 0.0(4) . .
O2 C8 C9 C10 -179.1(3) . .
C6 C8 C9 C10 -0.6(6) . .
C8 C9 C10 C11 177.8(4) . .
C8 C9 C10 C4 -1.0(5) . .
C3 C4 C10 C11 1.9(5) . .
C5 C4 C10 C11 -177.0(3) . .
C3 C4 C10 C9 -179.2(3) . .
C5 C4 C10 C9 1.8(5) . .
C9 C10 C11 C12 179.0(4) . .
C4 C10 C11 C12 -2.2(5) . .
C10 C11 C12 C1 -179.6(3) . 2_565
C10 C11 C12 C2 0.2(5) . .
C1 C2 C12 C11 -178.2(3) . .
C3 C2 C12 C11 2.1(5) . .
C1 C2 C12 C1 1.6(6) . 2_565
C3 C2 C12 C1 -178.2(3) . 2_565
C2 C1 C13 C14 -52(7) . .
C12 C1 C13 C14 127(6) 2_565 .
C1 C13 C14 Si1 42(13) . .
C18 Si1 C14 C13 131(8) . .
C15 Si1 C14 C13 -111(8) . .
C21 Si1 C14 C13 8(8) . .
C14 Si1 C15 C17 -175.4(3) . .
C18 Si1 C15 C17 -59.5(3) . .
C21 Si1 C15 C17 66.5(3) . .
C14 Si1 C15 C16 57.5(3) . .
C18 Si1 C15 C16 173.4(3) . .
C21 Si1 C15 C16 -60.6(3) . .
C14 Si1 C18 C19 68.5(3) . .
C15 Si1 C18 C19 -47.3(3) . .
C21 Si1 C18 C19 -171.7(3) . .
C14 Si1 C18 C20 -55.5(4) . .
C15 Si1 C18 C20 -171.3(3) . .
C21 Si1 C18 C20 64.2(4) . .
C14 Si1 C21 C22 160.2(3) . .
C18 Si1 C21 C22 41.1(4) . .
C15 Si1 C21 C22 -82.5(4) . .
C14 Si1 C21 C23' 19.7(12) . .
C18 Si1 C21 C23' -99.5(11) . .
C15 Si1 C21 C23' 136.9(11) . .
C14 Si1 C21 C23 42.3(9) . .
C18 Si1 C21 C23 -76.9(9) . .
C15 Si1 C21 C23 159.5(9) . .
loop_
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1 PubChem 12103946
