Enhancement of Antiaromatic Character via Additional Benzoannulation into Dibenzo[ a, f]pentalene: Syntheses and Properties of Benzo[ a]naphtho[2,1- f]pentalene and Dinaphtho[2,1- a, f]pentalene.
Konishi, Akihito; Okada, Yui; Kishi, Ryohei; Nakano, Masayoshi; Yasuda, Makoto; Journal of the American Chemical Society 141 (2019) 560–571; doi:10.1021/jacs.8b11530

data_4133598
_publ_section_title
;
 Enhancement of Antiaromatic Character via Additional Benzoannulation into
 Dibenzo[ a, f]pentalene: Syntheses and Properties of Benzo[
 a]naphtho[2,1- f]pentalene and Dinaphtho[2,1- a, f]pentalene.
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              560
_journal_page_last               571
_journal_paper_doi               10.1021/jacs.8b11530
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C41 H40 O S'
_chemical_formula_sum            'C41 H40 O S'
_chemical_formula_weight         580.83
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.3026(16)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   8.16835(13)
_cell_length_b                   12.1102(2)
_cell_length_c                   32.7192(6)
_cell_measurement_reflns_used    16905
_cell_measurement_temperature    123
_cell_measurement_theta_max      73.27
_cell_measurement_theta_min      3.85
_cell_volume                     3235.76(10)
_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  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXD Version 2013/2 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            38763
_diffrn_reflns_point_group_measured_fraction_full 0.762
_diffrn_reflns_point_group_measured_fraction_max 0.749
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         74.244
_diffrn_reflns_theta_min         3.650
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.111
_exptl_absorpt_correction_T_max  0.881
_exptl_absorpt_correction_T_min  0.676
_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            metalliclightoran
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1240.00
_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.114
_refine_diff_density_max         0.61
_refine_diff_density_min         -0.63
_refine_ls_abs_structure_details
;
 Flack x determined using 2802 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.88(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     804
_refine_ls_number_reflns         9872
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0751
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1617P)^2^+1.0688P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2168
_refine_ls_wR_factor_ref         0.2190
_reflns_Friedel_coverage         0.509
_reflns_Friedel_fraction_full    0.524
_reflns_Friedel_fraction_max     0.506
_reflns_number_gt                9483
_reflns_number_total             9872
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja8b11530_si_002.cif
_cod_data_source_block           xcalibur
_cod_database_code               4133598
_shelx_res_checksum              82187
_shelx_hkl_checksum              51375