#------------------------------------------------------------------------------
#$Date: 2019-11-03 10:32:28 +0200 (Sun, 03 Nov 2019) $
#$Revision: 221164 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/80/4128026.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_4128026
loop_
_publ_author_name
'Konishi, Akihito'
'Horii, Koki'
'Shiomi, Daisuke'
'Sato, Kazunobu'
'Takui, Takeji'
'Yasuda, Makoto'
_publ_section_title
;
 Open-Shell and Antiaromatic Character Induced by the Highly Symmetric
 Geometry of the Planar Heptalene Structure: Synthesis and
 Characterization of a Nonalternant Isomer of Bisanthene.
;
_journal_issue                   26
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10165
_journal_page_last               10170
_journal_paper_doi               10.1021/jacs.9b04080
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C52 H46 B2 F8'
_chemical_formula_sum            'C52 H46 B2 F8'
_chemical_formula_weight         844.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.756(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   28.2664(9)
_cell_length_b                   8.0077(2)
_cell_length_c                   18.2814(5)
_cell_measurement_reflns_used    8579
_cell_measurement_temperature    123
_cell_measurement_theta_max      30.43
_cell_measurement_theta_min      2.22
_cell_volume                     4137.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.805
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19849
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        30.900
_diffrn_reflns_theta_max         30.900
_diffrn_reflns_theta_min         2.228
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            metalliclightpurp
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1760.00
_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.92
_refine_diff_density_min         -0.78
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0667
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0800P)²+7.9504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1654
_refine_ls_wR_factor_ref         0.1788
_reflns_number_gt                4006
_reflns_number_total             5265
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja9b04080_si_003.cif
_cod_data_source_block           xcalibur
_cod_depositor_comments
;
The following automatic conversions were performed:
data name '_atom_site_symetry_multiplicity' replaced with
'_atom_site_symmetry_multiplicity' as specified in the replacement
file
'/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/lists/replacement-tags.lst'.

Automatic conversion script
Id: cif_correct_tags 4968 2017-02-21 14:55:21Z antanas 
;
_cod_database_code               4128026
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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
F1 F 0.60277(6) -0.15268(19) 0.44090(7) 0.0468(4) Uani 1 1 d .
F2 F 0.54631(9) -0.2207(3) 0.36031(13) 0.1091(10) Uani 1 1 d .
F3 F 0.57463(9) 0.0361(2) 0.36039(10) 0.0795(7) Uani 1 1 d .
F4 F 0.61941(8) -0.1695(3) 0.32025(9) 0.0922(9) Uani 1 1 d .
C1 C 0.59004(7) 0.0245(2) 0.60701(9) 0.0219(4) Uani 1 1 d .
C2 C 0.58273(7) 0.1619(2) 0.55870(10) 0.0224(4) Uani 1 1 d .
C3 C 0.61642(7) 0.2955(3) 0.56311(11) 0.0270(4) Uani 1 1 d .
H3 H 0.6420 0.2863 0.5971 0.032 Uiso 1 1 calc R
C4 C 0.61329(8) 0.4359(3) 0.52044(11) 0.0290(4) Uani 1 1 d .
H4 H 0.6370 0.5196 0.5242 0.035 Uiso 1 1 calc R
C5 C 0.57528(7) 0.4568(3) 0.47120(11) 0.0266(4) Uani 1 1 d .
H5 H 0.5726 0.5545 0.4420 0.032 Uiso 1 1 calc R
C6 C 0.54196(7) 0.3316(2) 0.46635(10) 0.0220(4) Uani 1 1 d .
C7 C 0.49978(7) 0.3233(2) 0.41989(10) 0.0220(4) Uani 1 1 d .
C8 C 0.48296(7) 0.4401(2) 0.37024(10) 0.0256(4) Uani 1 1 d .
H8 H 0.4983 0.5448 0.3646 0.031 Uiso 1 1 calc R
C9 C 0.44278(8) 0.4001(3) 0.32854(10) 0.0275(4) Uani 1 1 d .
H9 H 0.4308 0.4778 0.2937 0.033 Uiso 1 1 calc R
C10 C 0.42053(7) 0.2498(3) 0.33748(10) 0.0262(4) Uani 1 1 d .
H10 H 0.3936 0.2254 0.3078 0.031 Uiso 1 1 calc R
C11 C 0.43621(7) 0.1273(2) 0.38987(10) 0.0223(4) Uani 1 1 d .
C12 C 0.47737(7) 0.1687(2) 0.43168(9) 0.0206(4) Uani 1 1 d .
C13 C 0.50491(7) 0.0782(2) 0.48662(9) 0.0202(4) Uani 1 1 d .
C14 C 0.54475(7) 0.1828(2) 0.50771(9) 0.0206(4) Uani 1 1 d .
C15 C 0.62838(7) 0.0425(2) 0.66392(10) 0.0239(4) Uani 1 1 d .
C16 C 0.67449(7) -0.0094(3) 0.65097(10) 0.0287(4) Uani 1 1 d .
C17 C 0.70693(8) -0.0078(3) 0.70985(11) 0.0323(5) Uani 1 1 d .
H17 H 0.7384 -0.0448 0.7020 0.039 Uiso 1 1 calc R
C18 C 0.69440(8) 0.0461(3) 0.77911(11) 0.0305(5) Uani 1 1 d .
C19 C 0.64874(8) 0.1044(3) 0.78866(11) 0.0300(5) Uani 1 1 d .
H19 H 0.6403 0.1478 0.8351 0.036 Uiso 1 1 calc R
C20 C 0.61475(7) 0.1019(3) 0.73292(10) 0.0261(4) Uani 1 1 d .
C21 C 0.68927(8) -0.0690(3) 0.57634(12) 0.0390(6) Uani 1 1 d .
H21A H 0.7235 -0.0886 0.5765 0.047 Uiso 1 1 calc R
H21B H 0.6812 0.0160 0.5397 0.047 Uiso 1 1 calc R
H21C H 0.6727 -0.1732 0.5644 0.047 Uiso 1 1 calc R
C22 C 0.72820(9) 0.0328(3) 0.84537(12) 0.0389(6) Uani 1 1 d .
C23 C 0.56450(8) 0.1505(3) 0.74739(12) 0.0329(5) Uani 1 1 d .
H23A H 0.5635 0.2218 0.7909 0.040 Uiso 1 1 calc R
H23B H 0.5456 0.0498 0.7555 0.040 Uiso 1 1 calc R
H23C H 0.5516 0.2117 0.7052 0.040 Uiso 1 1 calc R
C24 C 0.72621(11) 0.1931(4) 0.89162(14) 0.0540(8) Uani 1 1 d .
H24A H 0.7503 0.1879 0.9306 0.065 Uiso 1 1 calc R
H24B H 0.6948 0.2035 0.9134 0.065 Uiso 1 1 calc R
H24C H 0.7322 0.2901 0.8604 0.065 Uiso 1 1 calc R
C25 C 0.71125(9) -0.1155(3) 0.89178(13) 0.0435(6) Uani 1 1 d .
H25A H 0.6789 -0.0946 0.9080 0.052 Uiso 1 1 calc R
H25B H 0.7322 -0.1286 0.9346 0.052 Uiso 1 1 calc R
H25C H 0.7119 -0.2178 0.8623 0.052 Uiso 1 1 calc R
C26 C 0.77938(9) 0.0030(4) 0.82284(14) 0.0498(7) Uani 1 1 d .
H26A H 0.7998 0.0009 0.8665 0.060 Uiso 1 1 calc R
H26B H 0.7895 0.0932 0.7903 0.060 Uiso 1 1 calc R
H26C H 0.7816 -0.1041 0.7972 0.060 Uiso 1 1 calc R
B1 B 0.58639(10) -0.1271(3) 0.36937(14) 0.0337(5) Uani 1 1 d .
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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
B B 0.0013 0.0007
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(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 127.75(16) . 5_656
C2 C1 C15 116.96(16) . .
C11 C1 C15 115.23(16) 5_656 .
C14 C2 C1 126.82(17) . .
C14 C2 C3 116.37(17) . .
C1 C2 C3 116.79(17) . .
C4 C3 C2 122.83(18) . .
C4 C3 H3 118.6 . .
C2 C3 H3 118.6 . .
C3 C4 C5 120.41(18) . .
C3 C4 H4 119.8 . .
C5 C4 H4 119.8 . .
C6 C5 C4 118.17(18) . .
C6 C5 H5 120.9 . .
C4 C5 H5 120.9 . .
C5 C6 C14 123.08(17) . .
C5 C6 C7 128.68(17) . .
C14 C6 C7 108.23(16) . .
C8 C7 C12 122.91(18) . .
C8 C7 C6 128.56(18) . .
C12 C7 C6 108.51(16) . .
C7 C8 C9 118.22(18) . .
C7 C8 H8 120.9 . .
C9 C8 H8 120.9 . .
C10 C9 C8 120.54(18) . .
C10 C9 H9 119.7 . .
C8 C9 H9 119.7 . .
C9 C10 C11 122.80(18) . .
C9 C10 H10 118.6 . .
C11 C10 H10 118.6 . .
C12 C11 C1 126.85(17) . 5_656
C12 C11 C10 116.22(17) . .
C1 C11 C10 116.90(17) 5_656 .
C7 C12 C11 119.27(16) . .
C7 C12 C13 107.80(16) . .
C11 C12 C13 132.88(17) . .
C13 C13 C14 126.2(2) 5_656 .
C13 C13 C12 126.2(2) 5_656 .
C14 C13 C12 107.57(16) . .
C6 C14 C2 119.09(17) . .
C6 C14 C13 107.88(16) . .
C2 C14 C13 133.04(17) . .
C16 C15 C20 121.46(17) . .
C16 C15 C1 121.54(17) . .
C20 C15 C1 116.81(18) . .
C15 C16 C17 118.06(19) . .
C15 C16 C21 121.29(17) . .
C17 C16 C21 120.6(2) . .
C18 C17 C16 122.0(2) . .
C18 C17 H17 119.0 . .
C16 C17 H17 119.0 . .
C19 C18 C17 117.97(18) . .
C19 C18 C22 119.6(2) . .
C17 C18 C22 122.3(2) . .
C18 C19 C20 122.56(19) . .
C18 C19 H19 118.7 . .
C20 C19 H19 118.7 . .
C19 C20 C15 117.8(2) . .
C19 C20 C23 120.90(18) . .
C15 C20 C23 121.15(17) . .
C16 C21 H21A 109.5 . .
C16 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C16 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C26 C22 C18 112.30(19) . .
C26 C22 C24 108.6(2) . .
C18 C22 C24 110.4(2) . .
C26 C22 C25 109.3(2) . .
C18 C22 C25 107.07(18) . .
C24 C22 C25 109.1(2) . .
C20 C23 H23A 109.5 . .
C20 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C20 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 . .
C22 C25 H25A 109.5 . .
C22 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C22 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C22 C26 H26A 109.5 . .
C22 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C22 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
F4 B1 F3 109.4(2) . .
F4 B1 F2 111.2(3) . .
F3 B1 F2 108.2(2) . .
F4 B1 F1 111.3(2) . .
F3 B1 F1 109.4(2) . .
F2 B1 F1 107.3(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 B1 1.397(3) .
F2 B1 1.367(3) .
F3 B1 1.358(3) .
F4 B1 1.347(3) .
C1 C2 1.425(3) .
C1 C11 1.425(3) 5_656
C1 C15 1.499(2) .
C2 C14 1.422(2) .
C2 C3 1.434(3) .
C3 C4 1.371(3) .
C3 H3 0.9500 .
C4 C5 1.402(3) .
C4 H4 0.9500 .
C5 C6 1.377(3) .
C5 H5 0.9500 .
C6 C14 1.413(3) .
C6 C7 1.456(3) .
C7 C8 1.383(3) .
C7 C12 1.409(3) .
C8 C9 1.397(3) .
C8 H8 0.9500 .
C9 C10 1.369(3) .
C9 H9 0.9500 .
C10 C11 1.437(3) .
C10 H10 0.9500 .
C11 C12 1.423(3) .
C11 C1 1.425(3) 5_656
C12 C13 1.456(2) .
C13 C13 1.374(4) 5_656
C13 C14 1.452(3) .
C15 C16 1.391(3) .
C15 C20 1.406(3) .
C16 C17 1.405(3) .
C16 C21 1.510(3) .
C17 C18 1.388(3) .
C17 H17 0.9500 .
C18 C19 1.386(3) .
C18 C22 1.536(3) .
C19 C20 1.391(3) .
C19 H19 0.9500 .
C20 C23 1.500(3) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 C26 1.528(4) .
C22 C24 1.539(4) .
C22 C25 1.540(3) .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 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 C14 6.3(3) 5_656 .
C15 C1 C2 C14 -170.69(18) . .
C11 C1 C2 C3 -175.47(19) 5_656 .
C15 C1 C2 C3 7.6(3) . .
C14 C2 C3 C4 -0.8(3) . .
C1 C2 C3 C4 -179.24(19) . .
C2 C3 C4 C5 1.9(3) . .
C3 C4 C5 C6 -1.0(3) . .
C4 C5 C6 C14 -1.0(3) . .
C4 C5 C6 C7 -179.85(19) . .
C5 C6 C7 C8 -0.8(3) . .
C14 C6 C7 C8 -179.76(19) . .
C5 C6 C7 C12 177.80(19) . .
C14 C6 C7 C12 -1.1(2) . .
C12 C7 C8 C9 -2.0(3) . .
C6 C7 C8 C9 176.43(19) . .
C7 C8 C9 C10 0.7(3) . .
C8 C9 C10 C11 1.0(3) . .
C9 C10 C11 C12 -1.4(3) . .
C9 C10 C11 C1 -179.53(19) . 5_656
C8 C7 C12 C11 1.5(3) . .
C6 C7 C12 C11 -177.16(17) . .
C8 C7 C12 C13 179.43(18) . .
C6 C7 C12 C13 0.7(2) . .
C1 C11 C12 C7 178.06(18) 5_656 .
C10 C11 C12 C7 0.2(3) . .
C1 C11 C12 C13 0.8(3) 5_656 .
C10 C11 C12 C13 -177.09(19) . .
C7 C12 C13 C13 -179.8(2) . 5_656
C11 C12 C13 C13 -2.3(4) . 5_656
C7 C12 C13 C14 -0.1(2) . .
C11 C12 C13 C14 177.4(2) . .
C5 C6 C14 C2 2.2(3) . .
C7 C6 C14 C2 -178.83(16) . .
C5 C6 C14 C13 -177.92(18) . .
C7 C6 C14 C13 1.1(2) . .
C1 C2 C14 C6 177.07(18) . .
C3 C2 C14 C6 -1.2(3) . .
C1 C2 C14 C13 -2.8(3) . .
C3 C2 C14 C13 178.9(2) . .
C13 C13 C14 C6 179.0(2) 5_656 .
C12 C13 C14 C6 -0.7(2) . .
C13 C13 C14 C2 -1.0(4) 5_656 .
C12 C13 C14 C2 179.26(19) . .
C2 C1 C15 C16 -91.3(2) . .
C11 C1 C15 C16 91.4(2) 5_656 .
C2 C1 C15 C20 93.7(2) . .
C11 C1 C15 C20 -83.7(2) 5_656 .
C20 C15 C16 C17 2.7(3) . .
C1 C15 C16 C17 -172.13(19) . .
C20 C15 C16 C21 -178.5(2) . .
C1 C15 C16 C21 6.7(3) . .
C15 C16 C17 C18 -1.1(3) . .
C21 C16 C17 C18 -180.0(2) . .
C16 C17 C18 C19 -2.0(3) . .
C16 C17 C18 C22 174.1(2) . .
C17 C18 C19 C20 3.6(3) . .
C22 C18 C19 C20 -172.52(19) . .
C18 C19 C20 C15 -2.1(3) . .
C18 C19 C20 C23 174.0(2) . .
C16 C15 C20 C19 -1.1(3) . .
C1 C15 C20 C19 173.91(18) . .
C16 C15 C20 C23 -177.3(2) . .
C1 C15 C20 C23 -2.2(3) . .
C19 C18 C22 C26 -167.7(2) . .
C17 C18 C22 C26 16.3(3) . .
C19 C18 C22 C24 -46.3(3) . .
C17 C18 C22 C24 137.7(2) . .
C19 C18 C22 C25 72.3(3) . .
C17 C18 C22 C25 -103.6(3) . .
