#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/68/1516833.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_1516833
loop_
_publ_author_name
'Bruzek, Matthew J.'
'Anthony, John E.'
_publ_section_title
;
 Synthesis and optical properties of dioxolane-functionalized hexacenes
 and heptacenes.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3608
_journal_page_last               3610
_journal_paper_doi               10.1021/ol501373s
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C48 H48 O6'
_chemical_formula_sum            'C48 H48 O6'
_chemical_formula_weight         720.86
_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                95.527(3)
_cell_angle_beta                 97.680(2)
_cell_angle_gamma                99.574(3)
_cell_formula_units_Z            1
_cell_length_a                   6.0156(2)
_cell_length_b                   8.3441(3)
_cell_length_c                   18.7234(6)
_cell_measurement_reflns_used    3967
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      66.45
_cell_measurement_theta_min      4.80
_cell_volume                     911.63(5)
_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 0.908
_diffrn_measured_fraction_theta_max 0.908
_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  0.0643
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4297
_diffrn_reflns_theta_full        67.53
_diffrn_reflns_theta_max         67.53
_diffrn_reflns_theta_min         2.40
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_max  0.907
_exptl_absorpt_correction_T_min  0.627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs in APEX2 (BrukerAXS, 2006)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4297
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0536
_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)+(0.0488P)²+1.5409P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1518
_refine_ls_wR_factor_ref         0.1536
_reflns_number_gt                3977
_reflns_number_total             4297
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol501373s_si_003.cif
_cod_data_source_block           x12417
_cod_database_code               1516833
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
O1 O 0.0630(3) 0.3585(2) 0.44810(10) 0.0206(5) Uani 1 1 d .
O2 O 0.1049(3) 1.3987(2) 0.22989(10) 0.0194(4) Uani 1 1 d .
O3 O 0.4877(3) 1.4993(2) 0.25868(10) 0.0195(4) Uani 1 1 d .
C1 C 0.2591(5) 0.4240(3) 0.47273(13) 0.0165(6) Uani 1 1 d .
C2 C 0.3555(5) 0.5890(3) 0.45588(13) 0.0171(6) Uani 1 1 d .
C3 C 0.2174(5) 0.6746(3) 0.41708(14) 0.0177(6) Uani 1 1 d .
H3 H 0.0613 0.6273 0.4019 0.021 Uiso 1 1 calc R
C4 C 0.3007(5) 0.8317(3) 0.39887(13) 0.0165(6) Uani 1 1 d .
C5 C 0.1608(5) 0.9215(3) 0.35969(13) 0.0173(6) Uani 1 1 d .
H5 H 0.0026 0.8779 0.3468 0.021 Uiso 1 1 calc R
C6 C 0.2459(5) 1.0722(3) 0.33908(14) 0.0176(6) Uani 1 1 d .
C7 C 0.1016(5) 1.1588(3) 0.29552(14) 0.0182(6) Uani 1 1 d .
H7 H -0.0580 1.1198 0.2834 0.022 Uiso 1 1 calc R
C8 C 0.2020(5) 1.2972(3) 0.27269(14) 0.0176(6) Uani 1 1 d .
C9 C 0.4379(5) 1.3603(3) 0.29146(13) 0.0177(6) Uani 1 1 d .
C10 C 0.5802(5) 1.2910(3) 0.33536(14) 0.0188(6) Uani 1 1 d .
H10 H 0.7362 1.3398 0.3495 0.023 Uiso 1 1 calc R
C11 C 0.4857(5) 1.1403(3) 0.35979(13) 0.0176(6) Uani 1 1 d .
C12 C 0.6225(5) 1.0536(3) 0.40112(13) 0.0170(6) Uani 1 1 d .
H12 H 0.7789 1.0999 0.4165 0.020 Uiso 1 1 calc R
C13 C 0.5371(5) 0.9009(3) 0.42075(13) 0.0163(6) Uani 1 1 d .
C14 C 0.6754(5) 0.8109(3) 0.46248(13) 0.0166(6) Uani 1 1 d .
H14 H 0.8319 0.8565 0.4782 0.020 Uiso 1 1 calc R
C15 C 0.5900(5) 0.6606(3) 0.48071(13) 0.0173(6) Uani 1 1 d .
C16 C 0.2930(5) 1.4923(3) 0.20231(14) 0.0180(6) Uani 1 1 d .
C17 C 0.3404(5) 1.3968(3) 0.13397(14) 0.0192(6) Uani 1 1 d .
H17A H 0.3613 1.2866 0.1457 0.023 Uiso 1 1 calc R
H17B H 0.4871 1.4522 0.1220 0.023 Uiso 1 1 calc R
C18 C 0.1611(5) 1.3751(4) 0.06561(15) 0.0238(7) Uani 1 1 d .
H18 H 0.1346 1.4862 0.0550 0.029 Uiso 1 1 calc R
C19 C -0.0670(5) 1.2735(4) 0.07315(16) 0.0326(8) Uani 1 1 d .
H19A H -0.1663 1.2530 0.0260 0.049 Uiso 1 1 calc R
H19B H -0.1390 1.3330 0.1086 0.049 Uiso 1 1 calc R
H19C H -0.0428 1.1689 0.0897 0.049 Uiso 1 1 calc R
C20 C 0.2554(6) 1.2980(4) 0.00183(16) 0.0317(8) Uani 1 1 d .
H20A H 0.2799 1.1879 0.0106 0.048 Uiso 1 1 calc R
H20B H 0.4006 1.3656 -0.0034 0.048 Uiso 1 1 calc R
H20C H 0.1464 1.2910 -0.0427 0.048 Uiso 1 1 calc R
C21 C 0.2448(5) 1.6623(3) 0.19439(14) 0.0188(6) Uani 1 1 d .
H21A H 0.2425 1.7179 0.2434 0.023 Uiso 1 1 calc R
H21B H 0.0902 1.6517 0.1664 0.023 Uiso 1 1 calc R
C22 C 0.4123(5) 1.7723(4) 0.15739(14) 0.0211(6) Uani 1 1 d .
H22 H 0.4222 1.7130 0.1092 0.025 Uiso 1 1 calc R
C23 C 0.6507(5) 1.8135(4) 0.20134(17) 0.0293(7) Uani 1 1 d .
H23A H 0.7489 1.8903 0.1774 0.044 Uiso 1 1 calc R
H23B H 0.7140 1.7131 0.2046 0.044 Uiso 1 1 calc R
H23C H 0.6427 1.8637 0.2502 0.044 Uiso 1 1 calc R
C24 C 0.3255(6) 1.9292(4) 0.14444(17) 0.0279(7) Uani 1 1 d .
H24A H 0.3154 1.9894 0.1911 0.042 Uiso 1 1 calc R
H24B H 0.1741 1.9026 0.1148 0.042 Uiso 1 1 calc R
H24C H 0.4309 1.9969 0.1190 0.042 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'
O O 0.0492 0.0322 '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_3
C8 O2 C16 105.0(2) .
C9 O3 C16 105.0(2) .
O1 C1 C2 121.1(2) .
O1 C1 C15 121.0(3) 2_666
C2 C1 C15 117.8(2) 2_666
C3 C2 C15 119.7(3) .
C3 C2 C1 119.3(2) .
C15 C2 C1 120.9(2) .
C2 C3 C4 121.7(3) .
C2 C3 H3 119.1 .
C4 C3 H3 119.1 .
C5 C4 C3 122.4(2) .
C5 C4 C13 118.8(2) .
C3 C4 C13 118.8(2) .
C6 C5 C4 122.0(3) .
C6 C5 H5 119.0 .
C4 C5 H5 119.0 .
C5 C6 C7 121.2(2) .
C5 C6 C11 119.1(3) .
C7 C6 C11 119.6(2) .
C8 C7 C6 117.3(3) .
C8 C7 H7 121.3 .
C6 C7 H7 121.3 .
C7 C8 O2 128.7(3) .
C7 C8 C9 122.6(3) .
O2 C8 C9 108.8(2) .
C10 C9 O3 128.3(3) .
C10 C9 C8 123.3(2) .
O3 C9 C8 108.5(2) .
C9 C10 C11 117.0(3) .
C9 C10 H10 121.5 .
C11 C10 H10 121.5 .
C12 C11 C10 121.2(3) .
C12 C11 C6 118.7(3) .
C10 C11 C6 120.1(2) .
C11 C12 C13 122.0(3) .
C11 C12 H12 119.0 .
C13 C12 H12 119.0 .
C12 C13 C14 122.5(2) .
C12 C13 C4 119.3(2) .
C14 C13 C4 118.2(2) .
C15 C14 C13 121.9(3) .
C15 C14 H14 119.1 .
C13 C14 H14 119.1 .
C14 C15 C2 119.5(3) .
C14 C15 C1 119.3(3) 2_666
C2 C15 C1 121.2(3) 2_666
O2 C16 O3 103.92(19) .
O2 C16 C21 109.0(2) .
O3 C16 C21 110.3(2) .
O2 C16 C17 109.7(2) .
O3 C16 C17 107.3(2) .
C21 C16 C17 115.9(2) .
C16 C17 C18 117.6(2) .
C16 C17 H17A 107.9 .
C18 C17 H17A 107.9 .
C16 C17 H17B 107.9 .
C18 C17 H17B 107.9 .
H17A C17 H17B 107.2 .
C19 C18 C20 109.9(3) .
C19 C18 C17 113.8(2) .
C20 C18 C17 109.0(2) .
C19 C18 H18 108.0 .
C20 C18 H18 108.0 .
C17 C18 H18 108.0 .
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 .
C16 C21 C22 116.2(2) .
C16 C21 H21A 108.2 .
C22 C21 H21A 108.2 .
C16 C21 H21B 108.2 .
C22 C21 H21B 108.2 .
H21A C21 H21B 107.4 .
C24 C22 C23 109.5(3) .
C24 C22 C21 110.1(2) .
C23 C22 C21 112.4(2) .
C24 C22 H22 108.2 .
C23 C22 H22 108.2 .
C21 C22 H22 108.2 .
C22 C23 H23A 109.5 .
C22 C23 H23B 109.5 .
H23A C23 H23B 109.5 .
C22 C23 H23C 109.5 .
H23A C23 H23C 109.5 .
H23B C23 H23C 109.5 .
C22 C24 H24A 109.5 .
C22 C24 H24B 109.5 .
H24A C24 H24B 109.5 .
C22 C24 H24C 109.5 .
H24A C24 H24C 109.5 .
H24B C24 H24C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.223(3) .
O2 C8 1.368(3) .
O2 C16 1.448(3) .
O3 C9 1.373(3) .
O3 C16 1.458(3) .
C1 C2 1.483(4) .
C1 C15 1.484(4) 2_666
C2 C3 1.365(4) .
C2 C15 1.433(4) .
C3 C4 1.414(4) .
C3 H3 0.9500 .
C4 C5 1.400(4) .
C4 C13 1.431(4) .
C5 C6 1.387(4) .
C5 H5 0.9500 .
C6 C7 1.440(4) .
C6 C11 1.446(4) .
C7 C8 1.347(4) .
C7 H7 0.9500 .
C8 C9 1.413(4) .
C9 C10 1.346(4) .
C10 C11 1.434(4) .
C10 H10 0.9500 .
C11 C12 1.390(4) .
C12 C13 1.395(4) .
C12 H12 0.9500 .
C13 C14 1.419(4) .
C14 C15 1.367(4) .
C14 H14 0.9500 .
C15 C1 1.484(4) 2_666
C16 C21 1.511(4) .
C16 C17 1.526(4) .
C17 C18 1.535(4) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.519(4) .
C18 C20 1.522(4) .
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 1.529(4) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 C24 1.517(4) .
C22 C23 1.523(4) .
C22 H22 1.0000 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 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
O1 C1 C2 C3 5.3(4) . .
C15 C1 C2 C3 -175.9(2) 2_666 .
O1 C1 C2 C15 -175.6(2) . .
C15 C1 C2 C15 3.1(4) 2_666 .
C15 C2 C3 C4 1.6(4) . .
C1 C2 C3 C4 -179.4(2) . .
C2 C3 C4 C5 -179.4(2) . .
C2 C3 C4 C13 1.1(4) . .
C3 C4 C5 C6 -176.9(2) . .
C13 C4 C5 C6 2.5(4) . .
C4 C5 C6 C7 176.7(2) . .
C4 C5 C6 C11 -1.2(4) . .
C5 C6 C7 C8 -174.4(2) . .
C11 C6 C7 C8 3.5(4) . .
C6 C7 C8 O2 178.4(2) . .
C6 C7 C8 C9 -1.7(4) . .
C16 O2 C8 C7 -160.9(3) . .
C16 O2 C8 C9 19.2(3) . .
C16 O3 C9 C10 164.2(3) . .
C16 O3 C9 C8 -16.8(3) . .
C7 C8 C9 C10 -2.2(4) . .
O2 C8 C9 C10 177.7(2) . .
C7 C8 C9 O3 178.7(2) . .
O2 C8 C9 O3 -1.4(3) . .
O3 C9 C10 C11 -177.1(2) . .
C8 C9 C10 C11 4.0(4) . .
C9 C10 C11 C12 175.5(2) . .
C9 C10 C11 C6 -2.0(4) . .
C5 C6 C11 C12 -1.3(4) . .
C7 C6 C11 C12 -179.2(2) . .
C5 C6 C11 C10 176.2(2) . .
C7 C6 C11 C10 -1.7(4) . .
C10 C11 C12 C13 -175.1(2) . .
C6 C11 C12 C13 2.4(4) . .
C11 C12 C13 C14 179.6(2) . .
C11 C12 C13 C4 -1.0(4) . .
C5 C4 C13 C12 -1.4(4) . .
C3 C4 C13 C12 178.0(2) . .
C5 C4 C13 C14 178.0(2) . .
C3 C4 C13 C14 -2.6(3) . .
C12 C13 C14 C15 -179.3(2) . .
C4 C13 C14 C15 1.3(4) . .
C13 C14 C15 C2 1.4(4) . .
C13 C14 C15 C1 -177.2(2) . 2_666
C3 C2 C15 C14 -2.9(4) . .
C1 C2 C15 C14 178.1(2) . .
C3 C2 C15 C1 175.8(2) . 2_666
C1 C2 C15 C1 -3.2(4) . 2_666
C8 O2 C16 O3 -28.8(2) . .
C8 O2 C16 C21 -146.4(2) . .
C8 O2 C16 C17 85.7(2) . .
C9 O3 C16 O2 27.9(3) . .
C9 O3 C16 C21 144.6(2) . .
C9 O3 C16 C17 -88.2(2) . .
O2 C16 C17 C18 68.9(3) . .
O3 C16 C17 C18 -178.8(2) . .
C21 C16 C17 C18 -55.0(3) . .
C16 C17 C18 C19 -64.6(3) . .
C16 C17 C18 C20 172.3(2) . .
O2 C16 C21 C22 -173.0(2) . .
O3 C16 C21 C22 73.5(3) . .
C17 C16 C21 C22 -48.8(3) . .
C16 C21 C22 C24 172.5(2) . .
C16 C21 C22 C23 -65.1(3) . .
