#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:40:22 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180349 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/18/7201835.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_7201835
loop_
_publ_author_name
'Chen, Jihua'
'Subramanian, Sankar'
'Parkin, Sean R.'
'Siegler, Maxime'
'Gallup, Kaitlin'
'Haughn, Chelsea'
'Martin, David C.'
'Anthony, John E.'
_publ_section_title
;
 The influence of side chains on the structures and properties of
 functionalized pentacenes
;
_journal_issue                   17
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              1961
_journal_paper_doi               10.1039/b717082c
_journal_volume                  18
_journal_year                    2008
_chemical_formula_moiety         'C38 H38'
_chemical_formula_sum            'C38 H38'
_chemical_formula_weight         494.68
_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                105.5261(9)
_cell_angle_beta                 100.2523(9)
_cell_angle_gamma                92.7360(9)
_cell_formula_units_Z            1
_cell_length_a                   6.6368(1)
_cell_length_b                   8.3446(2)
_cell_length_c                   13.7421(3)
_cell_measurement_reflns_used    3280
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     717.92(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0518
_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       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5024
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.57
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.9987
_exptl_absorpt_correction_T_min  0.9748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             266
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2513
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0474
_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)+(0.0755P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1343
_reflns_number_gt                1571
_reflns_number_total             2513
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            b717082c.txt
_cod_data_source_block           k04107
_cod_database_code               7201835
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
C1 C 0.3167(2) 0.58226(19) 0.49429(11) 0.0176(4) Uani 1 1 d . . .
C2 C 0.3829(2) 0.50182(18) 0.40214(11) 0.0191(4) Uani 1 1 d . . .
C3 C 0.2723(2) 0.50037(19) 0.30454(12) 0.0216(4) Uani 1 1 d . . .
H3 H 0.1467 0.5504 0.3001 0.026 Uiso 1 1 calc R . .
C4 C 0.3407(2) 0.42830(19) 0.21471(12) 0.0219(4) Uani 1 1 d . . .
C5 C 0.2314(3) 0.4299(2) 0.11542(12) 0.0294(5) Uani 1 1 d . . .
H5 H 0.1049 0.4786 0.1098 0.035 Uiso 1 1 calc R . .
C6 C 0.3062(3) 0.3625(2) 0.02893(13) 0.0334(5) Uani 1 1 d . . .
H6 H 0.2328 0.3665 -0.0363 0.040 Uiso 1 1 calc R . .
C7 C 0.4932(3) 0.2865(2) 0.03558(13) 0.0335(5) Uani 1 1 d . . .
H7 H 0.5433 0.2392 -0.0254 0.040 Uiso 1 1 calc R . .
C8 C 0.6008(3) 0.2806(2) 0.12776(13) 0.0297(5) Uani 1 1 d . . .
H8 H 0.7252 0.2286 0.1305 0.036 Uiso 1 1 calc R . .
C9 C 0.5308(2) 0.35123(19) 0.22112(12) 0.0230(4) Uani 1 1 d . . .
C10 C 0.6379(2) 0.34780(19) 0.31624(12) 0.0218(4) Uani 1 1 d . . .
H10 H 0.7613 0.2946 0.3197 0.026 Uiso 1 1 calc R . .
C11 C 0.5707(2) 0.42033(18) 0.40832(11) 0.0179(4) Uani 1 1 d . . .
C12 C 0.1360(2) 0.66897(19) 0.48851(11) 0.0202(4) Uani 1 1 d . . .
C13 C -0.0122(2) 0.74409(19) 0.48461(11) 0.0199(4) Uani 1 1 d . . .
C14 C -0.1981(2) 0.83236(19) 0.47558(11) 0.0197(4) Uani 1 1 d . . .
H14A H -0.1649 0.9494 0.5191 0.024 Uiso 1 1 calc R . .
H14B H -0.3046 0.7788 0.5020 0.024 Uiso 1 1 calc R . .
C15 C -0.2850(2) 0.83215(19) 0.36485(11) 0.0208(4) Uani 1 1 d . . .
H15A H -0.1809 0.8903 0.3394 0.025 Uiso 1 1 calc R . .
H15B H -0.3127 0.7153 0.3207 0.025 Uiso 1 1 calc R . .
C16 C -0.4820(2) 0.91708(19) 0.35567(11) 0.0200(4) Uani 1 1 d . . .
H16A H -0.5827 0.8634 0.3854 0.024 Uiso 1 1 calc R . .
H16B H -0.4520 1.0357 0.3967 0.024 Uiso 1 1 calc R . .
C17 C -0.5783(2) 0.90919(19) 0.24554(11) 0.0224(4) Uani 1 1 d . . .
H17A H -0.5981 0.7910 0.2034 0.027 Uiso 1 1 calc R . .
H17B H -0.4818 0.9705 0.2176 0.027 Uiso 1 1 calc R . .
C18 C -0.7840(2) 0.9823(2) 0.23495(12) 0.0284(5) Uani 1 1 d . . .
H18A H -0.7647 1.1004 0.2771 0.034 Uiso 1 1 calc R . .
H18B H -0.8811 0.9207 0.2624 0.034 Uiso 1 1 calc R . .
C19 C -0.8779(3) 0.9739(2) 0.12388(12) 0.0376(5) Uani 1 1 d . . .
H19A H -0.7856 1.0392 0.0973 0.056 Uiso 1 1 calc R . .
H19B H -1.0113 1.0198 0.1214 0.056 Uiso 1 1 calc R . .
H19C H -0.8972 0.8573 0.0816 0.056 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 0.0033 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'
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
_geom_angle_publ_flag
C11 C1 C2 120.79(14) 2_666 . ?
C11 C1 C12 119.79(13) 2_666 . ?
C2 C1 C12 119.41(13) . . ?
C3 C2 C1 121.90(14) . . ?
C3 C2 C11 118.72(14) . . ?
C1 C2 C11 119.38(13) . . ?
C4 C3 C2 122.13(14) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 122.37(15) . . ?
C3 C4 C9 119.11(14) . . ?
C5 C4 C9 118.50(14) . . ?
C6 C5 C4 120.90(16) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 120.40(16) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.74(16) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 121.19(15) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 122.44(15) . . ?
C10 C9 C4 119.31(14) . . ?
C8 C9 C4 118.25(14) . . ?
C9 C10 C11 122.35(15) . . ?
C9 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
C10 C11 C1 121.85(14) . 2_666 ?
C10 C11 C2 118.33(14) . . ?
C1 C11 C2 119.81(13) 2_666 . ?
C13 C12 C1 178.72(17) . . ?
C12 C13 C14 177.70(16) . . ?
C13 C14 C15 112.85(12) . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C16 C15 C14 112.44(12) . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C15 113.41(12) . . ?
C17 C16 H16A 108.9 . . ?
C15 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 C18 113.67(13) . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 C19 112.93(13) . . ?
C17 C18 H18A 109.0 . . ?
C19 C18 H18A 109.0 . . ?
C17 C18 H18B 109.0 . . ?
C19 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
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 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C11 1.418(2) 2_666 ?
C1 C2 1.420(2) . ?
C1 C12 1.431(2) . ?
C2 C3 1.406(2) . ?
C2 C11 1.448(2) . ?
C3 C4 1.386(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.431(2) . ?
C4 C9 1.442(2) . ?
C5 C6 1.362(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.421(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.353(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.430(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(2) . ?
C10 C11 1.408(2) . ?
C10 H10 0.9500 . ?
C11 C1 1.418(2) 2_666 ?
C12 C13 1.193(2) . ?
C13 C14 1.470(2) . ?
C14 C15 1.5277(18) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5187(19) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5170(19) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.521(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.5242(19) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C1 C2 C3 179.00(13) 2_666 . . . ?
C12 C1 C2 C3 -2.0(2) . . . . ?
C11 C1 C2 C11 -1.7(2) 2_666 . . . ?
C12 C1 C2 C11 177.33(13) . . . . ?
C1 C2 C3 C4 177.19(14) . . . . ?
C11 C2 C3 C4 -2.1(2) . . . . ?
C2 C3 C4 C5 -178.50(14) . . . . ?
C2 C3 C4 C9 0.4(2) . . . . ?
C3 C4 C5 C6 177.92(16) . . . . ?
C9 C4 C5 C6 -1.0(2) . . . . ?
C4 C5 C6 C7 1.1(3) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C7 C8 C9 C10 -179.67(15) . . . . ?
C7 C8 C9 C4 0.4(2) . . . . ?
C3 C4 C9 C10 1.4(2) . . . . ?
C5 C4 C9 C10 -179.69(14) . . . . ?
C3 C4 C9 C8 -178.74(15) . . . . ?
C5 C4 C9 C8 0.2(2) . . . . ?
C8 C9 C10 C11 178.72(15) . . . . ?
C4 C9 C10 C11 -1.4(2) . . . . ?
C9 C10 C11 C1 -179.25(14) . . . 2_666 ?
C9 C10 C11 C2 -0.3(2) . . . . ?
C3 C2 C11 C10 2.0(2) . . . . ?
C1 C2 C11 C10 -177.26(14) . . . . ?
C3 C2 C11 C1 -179.00(13) . . . 2_666 ?
C1 C2 C11 C1 1.7(2) . . . 2_666 ?
C13 C14 C15 C16 177.53(13) . . . . ?
C14 C15 C16 C17 -176.50(12) . . . . ?
C15 C16 C17 C18 175.61(13) . . . . ?
C16 C17 C18 C19 179.77(13) . . . . ?
