#------------------------------------------------------------------------------
#$Date: 2019-10-02 11:00:18 +0200 (Wed 02 de Oct de 2019) $
#$Revision: 219018 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/43/7234300.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_7234300
loop_
_publ_author_name
'Tien-Lin Wu'
'Chi-Hsien Kuo'
'Bo-Chao Lin'
'Yu-Tai Tao'
'Chao-Ping Hsu'
'Rai-Shung Liu'
_publ_section_title
;
 Synthesis of planar dibenzo[de,op]bistetracene derivatives for organic
 field-effect transistor applications: substituent effect on crystal
 packing and charge transport property
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              7583
_journal_page_last               7588
_journal_paper_doi               10.1039/C5TC01455G
_journal_volume                  3
_journal_year                    2015
_chemical_formula_moiety         'C17 H8'
_chemical_formula_sum            'C17 H8'
_chemical_formula_weight         212.23
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90.063(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5659(4)
_cell_length_b                   5.13300(10)
_cell_length_c                   15.5436(5)
_cell_measurement_reflns_used    6596
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.64
_cell_measurement_theta_min      2.62
_cell_volume                     922.79(5)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22871
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9905
_exptl_absorpt_correction_T_min  0.9306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       niddle
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.84
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1892
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0483
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0604P)²+0.6927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1419
_reflns_number_gt                1367
_reflns_number_total             1892
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2015-3-7583.cif
_cod_data_source_block           i14607
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7234300
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.87244(14) -0.3453(3) -0.07349(11) 0.0159(4) Uani 1 1 d U . .
C2 C 0.77963(15) -0.5008(3) -0.10231(11) 0.0177(4) Uani 1 1 d U . .
H2 H 0.7932 -0.6329 -0.1439 0.021 Uiso 1 1 calc R . .
C3 C 0.66991(15) -0.4634(4) -0.07099(12) 0.0219(4) Uani 1 1 d U . .
H3 H 0.6079 -0.5667 -0.0921 0.026 Uiso 1 1 calc R . .
C4 C 0.64918(15) -0.2751(3) -0.00860(12) 0.0205(4) Uani 1 1 d U . .
H4 H 0.573 -0.2524 0.0129 0.025 Uiso 1 1 calc R . .
C5 C 0.73821(15) -0.1192(3) 0.02285(11) 0.0167(4) Uani 1 1 d U . .
C6 C 0.71664(15) 0.0756(3) 0.09045(11) 0.0177(4) Uani 1 1 d U . .
C7 C 0.61008(15) 0.1030(4) 0.12984(12) 0.0229(4) Uani 1 1 d U . .
H7 H 0.5484 -0.0091 0.1136 0.027 Uiso 1 1 calc R . .
C8 C 0.59126(16) 0.2930(4) 0.19327(12) 0.0246(4) Uani 1 1 d U . .
H8 H 0.5174 0.3073 0.2196 0.029 Uiso 1 1 calc R . .
C9 C 0.67830(16) 0.4574(4) 0.21738(12) 0.0227(4) Uani 1 1 d U . .
H9 H 0.6646 0.5862 0.2601 0.027 Uiso 1 1 calc R . .
C10 C 0.78817(15) 0.4367(3) 0.17927(11) 0.0184(4) Uani 1 1 d U . .
C11 C 0.87892(15) 0.6073(3) 0.20244(11) 0.0193(4) Uani 1 1 d U . .
H11 H 0.8647 0.7426 0.2428 0.023 Uiso 1 1 calc R . .
C12 C 0.98658(15) 0.5809(3) 0.16781(11) 0.0183(4) Uani 1 1 d U . .
H12 H 1.046 0.6983 0.1845 0.022 Uiso 1 1 calc R . .
C13 C 1.01156(14) 0.3817(3) 0.10744(11) 0.0157(4) Uani 1 1 d U . .
C14 C 0.92247(14) 0.2147(3) 0.08016(10) 0.0148(4) Uani 1 1 d U . .
C15 C 0.94478(14) 0.0163(3) 0.01735(10) 0.0145(4) Uani 1 1 d U . .
C16 C 0.85107(14) -0.1494(3) -0.01124(10) 0.0153(4) Uani 1 1 d U . .
C17 C 0.80898(14) 0.2411(3) 0.11617(10) 0.0142(4) Uani 1 1 d U . .
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.421
-1 0 0 0.399
0 0 -1 0.055
0 0 1 0.067
0 -1 0 0.053
0 1 0 0.055
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 C16 119.02(16) . .
C2 C1 C13 120.94(16) . 3_755
C16 C1 C13 120.04(15) . 3_755
C3 C2 C1 120.78(16) . .
C3 C2 H2 119.6 . .
C1 C2 H2 119.6 . .
C2 C3 C4 120.30(16) . .
C2 C3 H3 119.8 . .
C4 C3 H3 119.8 . .
C3 C4 C5 121.09(16) . .
C3 C4 H4 119.5 . .
C5 C4 H4 119.5 . .
C4 C5 C16 119.13(16) . .
C4 C5 C6 121.00(16) . .
C16 C5 C6 119.86(15) . .
C7 C6 C17 118.94(16) . .
C7 C6 C5 122.45(16) . .
C17 C6 C5 118.60(15) . .
C6 C7 C8 121.34(17) . .
C6 C7 H7 119.3 . .
C8 C7 H7 119.3 . .
C9 C8 C7 120.47(17) . .
C9 C8 H8 119.8 . .
C7 C8 H8 119.8 . .
C8 C9 C10 120.25(17) . .
C8 C9 H9 119.9 . .
C10 C9 H9 119.9 . .
C9 C10 C11 121.12(17) . .
C9 C10 C17 119.78(16) . .
C11 C10 C17 119.10(15) . .
C12 C11 C10 121.05(16) . .
C12 C11 H11 119.5 . .
C10 C11 H11 119.5 . .
C11 C12 C13 121.32(16) . .
C11 C12 H12 119.3 . .
C13 C12 H12 119.3 . .
C14 C13 C12 119.31(15) . .
C14 C13 C1 119.24(15) . 3_755
C12 C13 C1 121.44(15) . 3_755
C13 C14 C17 119.73(15) . .
C13 C14 C15 120.39(15) . .
C17 C14 C15 119.87(15) . .
C15 C15 C14 120.88(19) 3_755 .
C15 C15 C16 119.71(19) 3_755 .
C14 C15 C16 119.41(15) . .
C1 C16 C5 119.60(15) . .
C1 C16 C15 119.70(15) . .
C5 C16 C15 120.70(15) . .
C6 C17 C10 119.18(15) . .
C6 C17 C14 121.44(15) . .
C10 C17 C14 119.39(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.410(2) .
C1 C16 1.417(2) .
C1 C13 1.454(2) 3_755
C2 C3 1.373(2) .
C2 H2 0.95 .
C3 C4 1.390(3) .
C3 H3 0.95 .
C4 C5 1.392(2) .
C4 H4 0.95 .
C5 C16 1.418(2) .
C5 C6 1.472(2) .
C6 C7 1.384(2) .
C6 C17 1.422(2) .
C7 C8 1.404(3) .
C7 H7 0.95 .
C8 C9 1.366(3) .
C8 H8 0.95 .
C9 C10 1.407(2) .
C9 H9 0.95 .
C10 C11 1.413(2) .
C10 C17 1.424(2) .
C11 C12 1.364(2) .
C11 H11 0.95 .
C12 C13 1.418(2) .
C12 H12 0.95 .
C13 C14 1.405(2) .
C13 C1 1.454(2) 3_755
C14 C17 1.434(2) .
C14 C15 1.434(2) .
C15 C15 1.397(3) 3_755
C15 C16 1.447(2) .
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
C16 C1 C2 C3 0.2(2) . . . .
C13 C1 C2 C3 -179.09(16) 3_755 . . .
C1 C2 C3 C4 -1.6(3) . . . .
C2 C3 C4 C5 0.6(3) . . . .
C3 C4 C5 C16 1.7(3) . . . .
C3 C4 C5 C6 -178.45(16) . . . .
C4 C5 C6 C7 4.2(3) . . . .
C16 C5 C6 C7 -175.95(16) . . . .
C4 C5 C6 C17 -175.95(16) . . . .
C16 C5 C6 C17 3.9(2) . . . .
C17 C6 C7 C8 1.1(3) . . . .
C5 C6 C7 C8 -179.02(16) . . . .
C6 C7 C8 C9 0.3(3) . . . .
C7 C8 C9 C10 -0.5(3) . . . .
C8 C9 C10 C11 179.10(17) . . . .
C8 C9 C10 C17 -0.9(3) . . . .
C9 C10 C11 C12 177.52(17) . . . .
C17 C10 C11 C12 -2.5(2) . . . .
C10 C11 C12 C13 0.0(3) . . . .
C11 C12 C13 C14 2.6(2) . . . .
C11 C12 C13 C1 -177.04(16) . . . 3_755
C12 C13 C14 C17 -2.5(2) . . . .
C1 C13 C14 C17 177.12(14) 3_755 . . .
C12 C13 C14 C15 178.26(15) . . . .
C1 C13 C14 C15 -2.1(2) 3_755 . . .
C13 C14 C15 C15 0.5(3) . . . 3_755
C17 C14 C15 C15 -178.72(18) . . . 3_755
C13 C14 C15 C16 -178.57(14) . . . .
C17 C14 C15 C16 2.2(2) . . . .
C2 C1 C16 C5 2.1(2) . . . .
C13 C1 C16 C5 -178.62(15) 3_755 . . .
C2 C1 C16 C15 -178.40(14) . . . .
C13 C1 C16 C15 0.9(2) 3_755 . . .
C4 C5 C16 C1 -3.0(2) . . . .
C6 C5 C16 C1 177.13(15) . . . .
C4 C5 C16 C15 177.49(15) . . . .
C6 C5 C16 C15 -2.4(2) . . . .
C15 C15 C16 C1 0.7(3) 3_755 . . .
C14 C15 C16 C1 179.80(14) . . . .
C15 C15 C16 C5 -179.78(18) 3_755 . . .
C14 C15 C16 C5 -0.7(2) . . . .
C7 C6 C17 C10 -2.4(2) . . . .
C5 C6 C17 C10 177.73(15) . . . .
C7 C6 C17 C14 177.44(16) . . . .
C5 C6 C17 C14 -2.5(2) . . . .
C9 C10 C17 C6 2.3(2) . . . .
C11 C10 C17 C6 -177.68(15) . . . .
C9 C10 C17 C14 -177.53(15) . . . .
C11 C10 C17 C14 2.5(2) . . . .
C13 C14 C17 C6 -179.84(15) . . . .
C15 C14 C17 C6 -0.6(2) . . . .
C13 C14 C17 C10 0.0(2) . . . .
C15 C14 C17 C10 179.23(15) . . . .
