#------------------------------------------------------------------------------
#$Date: 2019-11-03 10:32:08 +0200 (Sun, 03 Nov 2019) $
#$Revision: 221163 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/80/4128025.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_4128025
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         'C46 H34'
_chemical_formula_sum            'C46 H34'
_chemical_formula_weight         586.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                90.0000
_cell_angle_beta                 107.053(2)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   8.21746(18)
_cell_length_b                   24.3054(5)
_cell_length_c                   7.85743(16)
_cell_measurement_reflns_used    6016
_cell_measurement_temperature    123
_cell_measurement_theta_max      73.32
_cell_measurement_theta_min      3.59
_cell_volume                     1500.36(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_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    'Superflip (Palatinus, et al., 2007)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13858
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        74.160
_diffrn_reflns_theta_max         74.160
_diffrn_reflns_theta_min         3.637
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.554
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            metalliclightblac
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             620.00
_exptl_crystal_size_max          0.128
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3028
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0495P)²+0.7124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1082
_reflns_number_gt                2806
_reflns_number_total             3028
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja9b04080_si_002.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               4128025
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+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
C1 C 0.24791(16) 0.89642(5) 0.51322(17) 0.0214(3) Uani 1 1 d .
C2 C 0.26397(16) 0.92378(5) 0.67807(17) 0.0216(3) Uani 1 1 d .
C3 C 0.38640(17) 0.90225(5) 0.83437(18) 0.0250(3) Uani 1 1 d .
H3 H 0.4491 0.8705 0.8218 0.030 Uiso 1 1 calc R
C4 C 0.41761(17) 0.92507(6) 1.00033(18) 0.0266(3) Uani 1 1 d .
H4 H 0.4994 0.9087 1.0986 0.032 Uiso 1 1 calc R
C5 C 0.33053(17) 0.97216(5) 1.02674(18) 0.0247(3) Uani 1 1 d .
H5 H 0.3529 0.9886 1.1410 0.030 Uiso 1 1 calc R
C6 C 0.21044(16) 0.99403(5) 0.88027(17) 0.0215(3) Uani 1 1 d .
C7 C 0.10226(16) 1.04219(5) 0.87351(17) 0.0214(3) Uani 1 1 d .
C8 C 0.09784(17) 1.07721(5) 1.01139(18) 0.0249(3) Uani 1 1 d .
H8 H 0.1730 1.0723 1.1279 0.030 Uiso 1 1 calc R
C9 C -0.02071(17) 1.11986(5) 0.97308(18) 0.0246(3) Uani 1 1 d .
H9 H -0.0270 1.1446 1.0645 0.030 Uiso 1 1 calc R
C10 C -0.12902(17) 1.12634(5) 0.80296(18) 0.0235(3) Uani 1 1 d .
H10 H -0.2092 1.1556 0.7820 0.028 Uiso 1 1 calc R
C11 C -0.12767(16) 1.09165(5) 0.65674(17) 0.0208(3) Uani 1 1 d .
C12 C -0.00519(16) 1.04830(5) 0.69779(17) 0.0202(3) Uani 1 1 d .
C13 C 0.03695(15) 1.00418(5) 0.58942(17) 0.0196(3) Uani 1 1 d .
C14 C 0.17293(15) 0.97111(5) 0.70789(17) 0.0202(3) Uani 1 1 d .
C15 C 0.37001(16) 0.84988(5) 0.51886(17) 0.0218(3) Uani 1 1 d .
C16 C 0.32257(17) 0.79551(5) 0.54156(18) 0.0250(3) Uani 1 1 d .
C17 C 0.43835(17) 0.75305(5) 0.54937(19) 0.0270(3) Uani 1 1 d .
H17 H 0.4059 0.7163 0.5649 0.032 Uiso 1 1 calc R
C18 C 0.60059(18) 0.76319(6) 0.53495(19) 0.0276(3) Uani 1 1 d .
C19 C 0.64588(17) 0.81732(6) 0.51349(18) 0.0257(3) Uani 1 1 d .
H19 H 0.7563 0.8248 0.5037 0.031 Uiso 1 1 calc R
C20 C 0.53386(16) 0.86095(5) 0.50589(17) 0.0230(3) Uani 1 1 d .
C21 C 0.14851(18) 0.78296(6) 0.5598(2) 0.0328(3) Uani 1 1 d .
H21A H 0.1386 0.7433 0.5777 0.039 Uiso 1 1 calc R
H21B H 0.0611 0.7944 0.4513 0.039 Uiso 1 1 calc R
H21C H 0.1329 0.8030 0.6621 0.039 Uiso 1 1 calc R
C22 C 0.72354(19) 0.71638(6) 0.5426(2) 0.0362(4) Uani 1 1 d .
H22A H 0.6910 0.6849 0.6032 0.043 Uiso 1 1 calc R
H22B H 0.8389 0.7282 0.6082 0.043 Uiso 1 1 calc R
H22C H 0.7204 0.7058 0.4214 0.043 Uiso 1 1 calc R
C23 C 0.58984(17) 0.91924(6) 0.48921(19) 0.0272(3) Uani 1 1 d .
H23A H 0.5962 0.9394 0.5989 0.033 Uiso 1 1 calc R
H23B H 0.5076 0.9372 0.3885 0.033 Uiso 1 1 calc R
H23C H 0.7022 0.9190 0.4694 0.033 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 0.0181 0.0091
;
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)
;
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 127.17(11) . 3_576
C2 C1 C15 116.12(11) . .
C11 C1 C15 116.71(11) 3_576 .
C1 C2 C14 127.62(12) . .
C1 C2 C3 117.44(11) . .
C14 C2 C3 114.94(11) . .
C4 C3 C2 123.65(12) . .
C4 C3 H3 118.2 . .
C2 C3 H3 118.2 . .
C3 C4 C5 120.78(12) . .
C3 C4 H4 119.6 . .
C5 C4 H4 119.6 . .
C6 C5 C4 117.55(12) . .
C6 C5 H5 121.2 . .
C4 C5 H5 121.2 . .
C5 C6 C14 123.23(12) . .
C5 C6 C7 128.01(12) . .
C14 C6 C7 108.76(11) . .
C8 C7 C12 123.19(12) . .
C8 C7 C6 128.19(12) . .
C12 C7 C6 108.61(11) . .
C7 C8 C9 117.69(12) . .
C7 C8 H8 121.2 . .
C9 C8 H8 121.2 . .
C10 C9 C8 120.35(12) . .
C10 C9 H9 119.8 . .
C8 C9 H9 119.8 . .
C9 C10 C11 123.84(12) . .
C9 C10 H10 118.1 . .
C11 C10 H10 118.1 . .
C12 C11 C10 115.18(11) . .
C12 C11 C1 127.25(12) . 3_576
C10 C11 C1 117.56(11) . 3_576
C7 C12 C11 119.73(11) . .
C7 C12 C13 107.66(11) . .
C11 C12 C13 132.60(12) . .
C13 C13 C14 126.48(14) 3_576 .
C13 C13 C12 126.27(14) 3_576 .
C14 C13 C12 107.26(11) . .
C6 C14 C2 119.82(11) . .
C6 C14 C13 107.69(11) . .
C2 C14 C13 132.49(12) . .
C16 C15 C20 119.81(12) . .
C16 C15 C1 120.27(11) . .
C20 C15 C1 119.91(11) . .
C17 C16 C15 119.44(12) . .
C17 C16 C21 119.99(12) . .
C15 C16 C21 120.56(12) . .
C18 C17 C16 121.53(13) . .
C18 C17 H17 119.2 . .
C16 C17 H17 119.2 . .
C19 C18 C17 118.29(12) . .
C19 C18 C22 121.16(13) . .
C17 C18 C22 120.55(13) . .
C18 C19 C20 121.87(12) . .
C18 C19 H19 119.1 . .
C20 C19 H19 119.1 . .
C19 C20 C15 119.05(12) . .
C19 C20 C23 120.28(12) . .
C15 C20 C23 120.64(12) . .
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 . .
C18 C22 H22A 109.5 . .
C18 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C18 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
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 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.4272(18) .
C1 C11 1.4387(18) 3_576
C1 C15 1.5042(17) .
C2 C14 1.4287(18) .
C2 C3 1.4386(18) .
C3 C4 1.3702(19) .
C3 H3 0.9500 .
C4 C5 1.3972(19) .
C4 H4 0.9500 .
C5 C6 1.3837(18) .
C5 H5 0.9500 .
C6 C14 1.4124(18) .
C6 C7 1.4614(17) .
C7 C8 1.3865(18) .
C7 C12 1.4117(18) .
C8 C9 1.3936(19) .
C8 H8 0.9500 .
C9 C10 1.3806(19) .
C9 H9 0.9500 .
C10 C11 1.4277(18) .
C10 H10 0.9500 .
C11 C12 1.4273(17) .
C11 C1 1.4387(18) 3_576
C12 C13 1.4722(17) .
C13 C13 1.373(3) 3_576
C13 C14 1.4666(17) .
C15 C16 1.4038(18) .
C15 C20 1.4058(18) .
C16 C17 1.3929(18) .
C16 C21 1.5098(19) .
C17 C18 1.393(2) .
C17 H17 0.9500 .
C18 C19 1.391(2) .
C18 C22 1.5110(18) .
C19 C20 1.3941(18) .
C19 H19 0.9500 .
C20 C23 1.5070(18) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 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 -4.8(2) 3_576 .
C15 C1 C2 C14 175.50(12) . .
C11 C1 C2 C3 175.79(12) 3_576 .
C15 C1 C2 C3 -3.91(17) . .
C1 C2 C3 C4 178.58(13) . .
C14 C2 C3 C4 -0.90(19) . .
C2 C3 C4 C5 -0.6(2) . .
C3 C4 C5 C6 1.1(2) . .
C4 C5 C6 C14 -0.1(2) . .
C4 C5 C6 C7 179.29(12) . .
C5 C6 C7 C8 1.2(2) . .
C14 C6 C7 C8 -179.36(12) . .
C5 C6 C7 C12 -177.99(13) . .
C14 C6 C7 C12 1.42(14) . .
C12 C7 C8 C9 0.91(19) . .
C6 C7 C8 C9 -178.21(12) . .
C7 C8 C9 C10 0.0(2) . .
C8 C9 C10 C11 -0.7(2) . .
C9 C10 C11 C12 0.48(19) . .
C9 C10 C11 C1 -179.79(12) . 3_576
C8 C7 C12 C11 -1.17(19) . .
C6 C7 C12 C11 178.10(11) . .
C8 C7 C12 C13 179.56(12) . .
C6 C7 C12 C13 -1.17(14) . .
C10 C11 C12 C7 0.45(17) . .
C1 C11 C12 C7 -179.26(12) 3_576 .
C10 C11 C12 C13 179.51(12) . .
C1 C11 C12 C13 -0.2(2) 3_576 .
C7 C12 C13 C13 -179.20(15) . 3_576
C11 C12 C13 C13 1.7(3) . 3_576
C7 C12 C13 C14 0.52(13) . .
C11 C12 C13 C14 -178.62(13) . .
C5 C6 C14 C2 -1.51(19) . .
C7 C6 C14 C2 179.04(11) . .
C5 C6 C14 C13 178.38(12) . .
C7 C6 C14 C13 -1.07(14) . .
C1 C2 C14 C6 -177.53(12) . .
C3 C2 C14 C6 1.89(17) . .
C1 C2 C14 C13 2.6(2) . .
C3 C2 C14 C13 -177.97(12) . .
C13 C13 C14 C6 -179.93(15) 3_576 .
C12 C13 C14 C6 0.35(13) . .
C13 C13 C14 C2 -0.1(3) 3_576 .
C12 C13 C14 C2 -179.78(13) . .
C2 C1 C15 C16 94.18(15) . .
C11 C1 C15 C16 -85.56(15) 3_576 .
C2 C1 C15 C20 -84.21(15) . .
C11 C1 C15 C20 96.06(14) 3_576 .
C20 C15 C16 C17 -0.6(2) . .
C1 C15 C16 C17 -178.96(12) . .
C20 C15 C16 C21 178.65(13) . .
C1 C15 C16 C21 0.3(2) . .
C15 C16 C17 C18 -0.1(2) . .
C21 C16 C17 C18 -179.31(14) . .
C16 C17 C18 C19 0.4(2) . .
C16 C17 C18 C22 -179.59(13) . .
C17 C18 C19 C20 -0.1(2) . .
C22 C18 C19 C20 179.90(13) . .
C18 C19 C20 C15 -0.5(2) . .
C18 C19 C20 C23 177.78(13) . .
C16 C15 C20 C19 0.86(19) . .
C1 C15 C20 C19 179.25(12) . .
C16 C15 C20 C23 -177.43(12) . .
C1 C15 C20 C23 0.97(19) . .
