Dibenzo[<i>hi</i>,<i>st</i>]ovalene as Highly Luminescent Nanographene: Efficient Synthesis via Photochemical Cyclodehydroiodination, Optoelectronic Properties, and Single-Molecule Spectroscopy.
Chen, Qiang; Thoms, Stefan; Stöttinger, Sven; Schollmeyer, Dieter; Müllen, Klaus; Narita, Akimitsu; Basché, Thomas; Journal of the American Chemical Society 141 (2019) 16439–16449; doi:10.1021/jacs.9b08320

data_4127702
_publ_section_title
;
 Dibenzo[<i>hi</i>,<i>st</i>]ovalene as Highly Luminescent Nanographene:
 Efficient Synthesis via Photochemical Cyclodehydroiodination,
 Optoelectronic Properties, and Single-Molecule Spectroscopy.
;
_journal_issue                   41
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16439
_journal_page_last               16449
_journal_paper_doi               10.1021/jacs.9b08320
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C38 H18 O2, C2 H3 N'
_chemical_formula_sum            'C40 H21 N O2'
_chemical_formula_weight         547.58
_chemical_name_systematic
5,14-diformylbenzo[a]dinaphtho[2,1,8-cde:1',2',3',4'-ghi]perylene
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   24.2958(5)
_cell_length_b                   17.0876(2)
_cell_length_c                   24.3610(3)
_cell_measurement_reflns_used    77793
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      1.68
_cell_volume                     10113.6(3)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SIR-2004
_diffrn_ambient_temperature      193(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      ' 275 frames, detector distance = 80 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            94183
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.445
_diffrn_reflns_theta_min         1.676
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       needle
_exptl_crystal_F_000             4544
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     778
_refine_ls_number_reflns         13022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0878
_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/[\s^2^(Fo^2^)+(0.0185P)^2^+31.5257P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1855
_refine_ls_wR_factor_ref         0.1999
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10483
_reflns_number_total             13022
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b08320_si_002.cif
_cod_data_source_block           kmu5
_cod_database_code               4127702
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.952
_shelx_estimated_absorpt_t_max   0.992
_shelx_res_checksum              82390
_shelx_hkl_checksum              3673