#------------------------------------------------------------------------------
#$Date: 2020-01-31 02:29:29 +0200 (Fri, 31 Jan 2020) $
#$Revision: 247395 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/71/1557195.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_1557195
loop_
_publ_author_name
'Shibuya, Yusuke'
'Aonuma, Kazuhiro'
'Kimura, Tomohiro'
'Kaneko, Takuro'
'Fujiwara, Wataru'
'Yamaguchi, Yuji'
'Kumaki, Daisuke'
'Tokito, Shizuo'
'Katagiri, Hiroshi'
_publ_section_title
;
 Linear Biazulene Isomers: Effects of Molecular and Packing Structure on
 Optoelectronic and Charge-Transport Properties
;
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_paper_doi               10.1021/acs.jpcc.9b11214
_journal_year                    2020
_chemical_formula_moiety         'C20 H14'
_chemical_formula_sum            'C20 H14'
_chemical_formula_weight         254.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                86.684(5)
_cell_angle_beta                 87.090(5)
_cell_angle_gamma                88.848(5)
_cell_formula_units_Z            2
_cell_length_a                   5.9457(3)
_cell_length_b                   7.8815(5)
_cell_length_c                   14.0822(8)
_cell_measurement_reflns_used    3019
_cell_measurement_temperature    296
_cell_measurement_theta_max      30.0640
_cell_measurement_theta_min      2.5950
_cell_volume                     657.85(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8859
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.895
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Blue
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2996
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1123
_refine_ls_R_factor_gt           0.0583
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0670P)²+0.0136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1269
_refine_ls_wR_factor_ref         0.1522
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1753
_reflns_number_total             2996
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp9b11214_si_003.cif
_cod_data_source_block           BiAz2_rt_20180921
_cod_database_code               1557195
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.988
_shelx_estimated_absorpt_t_max   0.998
_oxdiff_exptl_absorpt_empirical_full_min 0.899
_oxdiff_exptl_absorpt_empirical_full_max 1.693
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.0034(3) 0.0244(2) 0.54836(13) 0.0479(5) Uani 1 1 d . .
C2 C -0.1616(3) -0.0086(2) 0.62186(14) 0.0518(5) Uani 1 1 d . .
H2 H -0.2955 -0.0648 0.6152 0.062 Uiso 1 1 calc R U
C3 C -0.0960(3) 0.0543(2) 0.70502(14) 0.0474(5) Uani 1 1 d . .
C4 C -0.2094(3) 0.0415(2) 0.79318(15) 0.0546(5) Uani 1 1 d . .
H4 H -0.3477 -0.0119 0.7945 0.066 Uiso 1 1 calc R U
C5 C -0.1490(4) 0.0958(3) 0.87938(15) 0.0627(6) Uani 1 1 d . .
H5 H -0.2499 0.0721 0.9308 0.075 Uiso 1 1 calc R U
C6 C 0.0437(4) 0.1817(3) 0.89942(16) 0.0643(6) Uani 1 1 d . .
H6 H 0.0530 0.2076 0.9627 0.077 Uiso 1 1 calc R U
C7 C 0.2224(4) 0.2339(3) 0.83972(15) 0.0599(6) Uani 1 1 d . .
H7 H 0.3338 0.2916 0.8681 0.072 Uiso 1 1 calc R U
C8 C 0.2594(3) 0.2127(2) 0.74365(15) 0.0544(5) Uani 1 1 d . .
H8 H 0.3928 0.2573 0.7165 0.065 Uiso 1 1 calc R U
C9 C 0.1260(3) 0.1345(2) 0.68191(14) 0.0467(5) Uani 1 1 d . .
C10 C 0.1757(3) 0.1133(2) 0.58680(14) 0.0505(5) Uani 1 1 d . .
H10 H 0.3047 0.1522 0.5530 0.061 Uiso 1 1 calc R U
C11 C 0.5049(3) 0.5244(2) 0.54842(13) 0.0488(5) Uani 1 1 d . .
C12 C 0.3383(3) 0.6180(2) 0.59846(14) 0.0527(5) Uani 1 1 d . .
H12 H 0.2056 0.6612 0.5736 0.063 Uiso 1 1 calc R U
C13 C 0.4024(3) 0.6359(2) 0.69016(14) 0.0473(5) Uani 1 1 d . .
C14 C 0.2777(3) 0.7158(2) 0.76115(15) 0.0559(5) Uani 1 1 d . .
H14 H 0.1422 0.7656 0.7430 0.067 Uiso 1 1 calc R U
C15 C 0.3264(4) 0.7316(3) 0.85461(16) 0.0628(6) Uani 1 1 d . .
H15 H 0.2198 0.7912 0.8908 0.075 Uiso 1 1 calc R U
C16 C 0.5122(4) 0.6710(3) 0.90212(16) 0.0664(6) Uani 1 1 d . .
H16 H 0.5105 0.6931 0.9663 0.080 Uiso 1 1 calc R U
C17 C 0.7004(4) 0.5825(3) 0.86843(16) 0.0645(6) Uani 1 1 d . .
H17 H 0.8074 0.5544 0.9129 0.077 Uiso 1 1 calc R U
C18 C 0.7505(3) 0.5305(2) 0.77808(15) 0.0558(5) Uani 1 1 d . .
H18 H 0.8886 0.4744 0.7697 0.067 Uiso 1 1 calc R U
C19 C 0.6254(3) 0.5495(2) 0.69788(14) 0.0482(5) Uani 1 1 d . .
C20 C 0.6799(3) 0.4861(2) 0.60983(14) 0.0510(5) Uani 1 1 d . .
H20 H 0.8122 0.4271 0.5938 0.061 Uiso 1 1 calc R 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 0.0000 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_3
C10 C1 C2 107.29(17) .
C10 C1 C1 126.4(2) 2_556
C2 C1 C1 126.3(2) 2_556
C3 C2 C1 110.03(17) .
C3 C2 H2 125.0 .
C1 C2 H2 125.0 .
C2 C3 C4 127.10(18) .
C2 C3 C9 106.21(17) .
C4 C3 C9 126.67(18) .
C5 C4 C3 129.9(2) .
C5 C4 H4 115.1 .
C3 C4 H4 115.1 .
C4 C5 C6 128.4(2) .
C4 C5 H5 115.8 .
C6 C5 H5 115.8 .
C7 C6 C5 129.7(2) .
C7 C6 H6 115.1 .
C5 C6 H6 115.1 .
C6 C7 C8 129.0(2) .
C6 C7 H7 115.5 .
C8 C7 H7 115.5 .
C7 C8 C9 129.22(19) .
C7 C8 H8 115.4 .
C9 C8 H8 115.4 .
C10 C9 C8 126.37(18) .
C10 C9 C3 106.44(16) .
C8 C9 C3 127.19(18) .
C9 C10 C1 110.02(16) .
C9 C10 H10 125.0 .
C1 C10 H10 125.0 .
C20 C11 C12 107.80(18) .
C20 C11 C11 126.4(2) 2_666
C12 C11 C11 125.8(2) 2_666
C13 C12 C11 109.50(17) .
C13 C12 H12 125.2 .
C11 C12 H12 125.2 .
C12 C13 C14 125.99(19) .
C12 C13 C19 106.66(17) .
C14 C13 C19 127.33(19) .
C15 C14 C13 129.1(2) .
C15 C14 H14 115.5 .
C13 C14 H14 115.5 .
C14 C15 C16 128.8(2) .
C14 C15 H15 115.6 .
C16 C15 H15 115.6 .
C15 C16 C17 129.7(2) .
C15 C16 H16 115.2 .
C17 C16 H16 115.2 .
C18 C17 C16 128.8(2) .
C18 C17 H17 115.6 .
C16 C17 H17 115.6 .
C17 C18 C19 129.4(2) .
C17 C18 H18 115.3 .
C19 C18 H18 115.3 .
C18 C19 C20 126.67(19) .
C18 C19 C13 126.86(19) .
C20 C19 C13 106.44(16) .
C19 C20 C11 109.59(17) .
C19 C20 H20 125.2 .
C11 C20 H20 125.2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C10 1.401(2) .
C1 C2 1.406(3) .
C1 C1 1.439(4) 2_556
C2 C3 1.375(3) .
C2 H2 0.9300 .
C3 C4 1.382(3) .
C3 C9 1.488(2) .
C4 C5 1.377(3) .
C4 H4 0.9300 .
C5 C6 1.391(3) .
C5 H5 0.9300 .
C6 C7 1.376(3) .
C6 H6 0.9300 .
C7 C8 1.379(3) .
C7 H7 0.9300 .
C8 C9 1.384(3) .
C8 H8 0.9300 .
C9 C10 1.376(3) .
C10 H10 0.9300 .
C11 C20 1.404(3) .
C11 C12 1.408(3) .
C11 C11 1.442(4) 2_666
C12 C13 1.381(3) .
C12 H12 0.9300 .
C13 C14 1.387(3) .
C13 C19 1.484(3) .
C14 C15 1.375(3) .
C14 H14 0.9300 .
C15 C16 1.383(3) .
C15 H15 0.9300 .
C16 C17 1.385(3) .
C16 H16 0.9300 .
C17 C18 1.376(3) .
C17 H17 0.9300 .
C18 C19 1.383(3) .
C18 H18 0.9300 .
C19 C20 1.384(3) .
C20 H20 0.9300 .
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
C10 C1 C2 C3 -1.0(2) .
C1 C1 C2 C3 178.9(2) 2_556
C1 C2 C3 C4 -177.67(17) .
C1 C2 C3 C9 0.6(2) .
C2 C3 C4 C5 177.3(2) .
C9 C3 C4 C5 -0.6(3) .
C3 C4 C5 C6 1.3(4) .
C4 C5 C6 C7 -0.2(4) .
C5 C6 C7 C8 -1.0(4) .
C6 C7 C8 C9 0.5(4) .
C7 C8 C9 C10 -178.07(19) .
C7 C8 C9 C3 0.8(3) .
C2 C3 C9 C10 0.0(2) .
C4 C3 C9 C10 178.28(18) .
C2 C3 C9 C8 -179.01(18) .
C4 C3 C9 C8 -0.7(3) .
C8 C9 C10 C1 178.42(17) .
C3 C9 C10 C1 -0.6(2) .
C2 C1 C10 C9 1.0(2) .
C1 C1 C10 C9 -178.9(2) 2_556
C20 C11 C12 C13 -1.4(2) .
C11 C11 C12 C13 178.1(2) 2_666
C11 C12 C13 C14 -177.79(17) .
C11 C12 C13 C19 0.7(2) .
C12 C13 C14 C15 176.85(19) .
C19 C13 C14 C15 -1.4(3) .
C13 C14 C15 C16 -0.4(4) .
C14 C15 C16 C17 1.7(4) .
C15 C16 C17 C18 -0.5(4) .
C16 C17 C18 C19 -1.5(4) .
C17 C18 C19 C20 -176.3(2) .
C17 C18 C19 C13 1.2(3) .
C12 C13 C19 C18 -177.67(18) .
C14 C13 C19 C18 0.8(3) .
C12 C13 C19 C20 0.2(2) .
C14 C13 C19 C20 178.65(17) .
C18 C19 C20 C11 176.84(18) .
C13 C19 C20 C11 -1.0(2) .
C12 C11 C20 C19 1.5(2) .
C11 C11 C20 C19 -178.0(2) 2_666
