#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/74/1507424.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_1507424
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            'C34 H30'
_chemical_formula_weight         438.58
_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                 124.441(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.0740(14)
_cell_length_b                   6.4820(4)
_cell_length_c                   19.2460(11)
_cell_measurement_reflns_used    10809
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     2579.7(3)
_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      173(1)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full .995
_diffrn_measured_fraction_theta_max .995
_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  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0640
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9518
_diffrn_reflns_theta_full        27.31
_diffrn_reflns_theta_max         27.31
_diffrn_reflns_theta_min         2.18
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_refine_diff_density_max         .175
_refine_diff_density_min         -.169
_refine_diff_density_rms         .035
_refine_ls_extinction_coef       0.0038(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2898
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0606
_refine_ls_shift/su_max          2.845
_refine_ls_shift/su_mean         0.135
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0468P)²+1.0626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1323
_reflns_number_gt                2025
_reflns_number_total             2898
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0167356_s2.cif
_cod_data_source_block           k01105
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1507424
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
C1 C 0.20052(7) 0.2796(2) 0.41310(9) 0.0258(4) Uani 1 1 d .
C2 C 0.20787(7) 0.4233(2) 0.47309(9) 0.0254(4) Uani 1 1 d .
C3 C 0.16768(7) 0.5981(3) 0.44938(10) 0.0277(4) Uani 1 1 d .
H3 H 0.1347(7) 0.619(2) 0.3914(10) 0.033 Uiso 1 1 calc .
C4 C 0.17438(7) 0.7402(2) 0.50717(9) 0.0274(4) Uani 1 1 d .
C5 C 0.13455(8) 0.9214(3) 0.48273(11) 0.0322(4) Uani 1 1 d .
H5 H 0.1014(8) 0.943(2) 0.4249(11) 0.039 Uiso 1 1 calc .
C6 C 0.14333(8) 1.0607(3) 0.54019(11) 0.0360(4) Uani 1 1 d .
H6 H 0.1165(8) 1.180(3) 0.5225(10) 0.043 Uiso 1 1 calc .
C7 C 0.19249(8) 1.0312(3) 0.62725(11) 0.0354(4) Uani 1 1 d .
H7 H 0.1984(8) 1.131(3) 0.6672(11) 0.042 Uiso 1 1 calc .
C8 C 0.23095(8) 0.8624(3) 0.65371(10) 0.0327(4) Uani 1 1 d .
H8 H 0.2632(8) 0.845(3) 0.7121(10) 0.039 Uiso 1 1 calc .
C9 C 0.22399(7) 0.7103(2) 0.59539(9) 0.0279(4) Uani 1 1 d .
C10 C 0.26381(7) 0.5386(3) 0.61990(10) 0.0283(4) Uani 1 1 d .
H10 H 0.2961(7) 0.518(2) 0.6781(10) 0.034 Uiso 1 1 calc .
C11 C 0.25799(7) 0.3941(2) 0.56159(9) 0.0261(4) Uani 1 1 d .
C12 C 0.15074(7) 0.3091(2) 0.32561(9) 0.0279(4) Uani 1 1 d .
C13 C 0.10954(7) 0.3339(3) 0.25257(9) 0.0289(4) Uani 1 1 d .
C14 C 0.06058(7) 0.3678(3) 0.16188(9) 0.0319(4) Uani 1 1 d .
C15 C 0.00072(8) 0.4703(3) 0.14872(11) 0.0512(6) Uani 1 1 d .
H15A H -0.0181 0.3798 0.1703 0.077 Uiso 1 1 calc R
H15B H -0.0311 0.4947 0.0885 0.077 Uiso 1 1 calc R
H15C H 0.0129 0.6020 0.1789 0.077 Uiso 1 1 calc R
C16 C 0.09006(9) 0.5037(4) 0.12680(11) 0.0544(6) Uani 1 1 d .
H16A H 0.1017 0.6380 0.1551 0.082 Uiso 1 1 calc R
H16B H 0.0585 0.5233 0.0661 0.082 Uiso 1 1 calc R
H16C H 0.1288 0.4368 0.1367 0.082 Uiso 1 1 calc R
C17 C 0.04192(9) 0.1587(3) 0.11683(12) 0.0558(6) Uani 1 1 d .
H17A H 0.0807 0.0905 0.1272 0.084 Uiso 1 1 calc R
H17B H 0.0109 0.1798 0.0561 0.084 Uiso 1 1 calc R
H17C H 0.0223 0.0720 0.1383 0.084 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'
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
C2 C1 C11 120.74(13) . 7_556
C2 C1 C12 119.81(14) . .
C11 C1 C12 119.45(14) 7_556 .
C3 C2 C1 121.77(14) . .
C3 C2 C11 118.18(14) . .
C1 C2 C11 120.05(14) . .
C4 C3 C2 122.48(14) . .
C4 C3 H3 119.7(9) . .
C2 C3 H3 117.8(9) . .
C3 C4 C5 122.45(14) . .
C3 C4 C9 119.35(15) . .
C5 C4 C9 118.19(15) . .
C6 C5 C4 121.24(16) . .
C6 C5 H5 121.9(10) . .
C4 C5 H5 116.8(10) . .
C5 C6 C7 120.49(17) . .
C5 C6 H6 120.9(10) . .
C7 C6 H6 118.6(10) . .
C8 C7 C6 120.65(17) . .
C8 C7 H7 120.3(10) . .
C6 C7 H7 119.1(10) . .
C7 C8 C9 121.20(15) . .
C7 C8 H8 121.7(10) . .
C9 C8 H8 117.1(10) . .
C10 C9 C8 122.80(14) . .
C10 C9 C4 118.95(14) . .
C8 C9 C4 118.23(15) . .
C9 C10 C11 122.25(14) . .
C9 C10 H10 119.2(10) . .
C11 C10 H10 118.6(9) . .
C10 C11 C1 122.00(13) . 7_556
C10 C11 C2 118.79(14) . .
C1 C11 C2 119.21(14) 7_556 .
C13 C12 C1 179.57(16) . .
C12 C13 C14 177.75(16) . .
C13 C14 C15 110.07(13) . .
C13 C14 C16 108.73(13) . .
C15 C14 C16 110.56(15) . .
C13 C14 C17 108.73(14) . .
C15 C14 C17 109.52(15) . .
C16 C14 C17 109.18(15) . .
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 . .
C14 C17 H17A 109.5 . .
C14 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C14 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.412(2) .
C1 C11 1.419(2) 7_556
C1 C12 1.433(2) .
C2 C3 1.410(2) .
C2 C11 1.447(2) .
C3 C4 1.379(2) .
C3 H3 0.987(15) .
C4 C5 1.437(2) .
C4 C9 1.442(2) .
C5 C6 1.346(2) .
C5 H5 0.990(17) .
C6 C7 1.424(2) .
C6 H6 0.991(18) .
C7 C8 1.353(2) .
C7 H7 0.970(17) .
C8 C9 1.428(2) .
C8 H8 0.987(16) .
C9 C10 1.388(2) .
C10 C11 1.405(2) .
C10 H10 0.981(15) .
C11 C1 1.419(2) 7_556
C12 C13 1.194(2) .
C13 C14 1.476(2) .
C14 C15 1.526(2) .
C14 C16 1.531(2) .
C14 C17 1.533(3) .
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 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 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 179.35(14) 7_556 .
C12 C1 C2 C3 -0.6(2) . .
C11 C1 C2 C11 -0.2(2) 7_556 .
C12 C1 C2 C11 179.86(13) . .
C1 C2 C3 C4 -179.77(14) . .
C11 C2 C3 C4 -0.2(2) . .
C2 C3 C4 C5 178.25(14) . .
C2 C3 C4 C9 -0.3(2) . .
C3 C4 C5 C6 -178.06(15) . .
C9 C4 C5 C6 0.5(2) . .
C4 C5 C6 C7 -0.3(3) . .
C5 C6 C7 C8 -0.3(3) . .
C6 C7 C8 C9 0.7(2) . .
C7 C8 C9 C10 177.95(15) . .
C7 C8 C9 C4 -0.5(2) . .
C3 C4 C9 C10 0.0(2) . .
C5 C4 C9 C10 -178.60(14) . .
C3 C4 C9 C8 178.48(14) . .
C5 C4 C9 C8 -0.1(2) . .
C8 C9 C10 C11 -177.61(14) . .
C4 C9 C10 C11 0.8(2) . .
C9 C10 C11 C1 179.05(14) . 7_556
C9 C10 C11 C2 -1.3(2) . .
C3 C2 C11 C10 0.9(2) . .
C1 C2 C11 C10 -179.48(13) . .
C3 C2 C11 C1 -179.37(13) . 7_556
C1 C2 C11 C1 0.2(2) . 7_556
C2 C1 C12 C13 113(43) . .
C11 C1 C12 C13 -67(76) 7_556 .
C1 C12 C13 C14 -12(45) . .
C12 C13 C14 C15 -135(5) . .
C12 C13 C14 C16 -13(5) . .
C12 C13 C14 C17 105(5) . .
