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_4127701
_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         'C54 H32'
_chemical_formula_sum            'C54 H32'
_chemical_formula_weight         680.79
_chemical_name_systematic
6,14-bis(2,6-dimethylphenyl)dibenzo[hi,st]ovalene
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 93.916(19)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.9726(19)
_cell_length_b                   17.601(3)
_cell_length_c                   12.768(3)
_cell_measurement_reflns_used    3846
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.99
_cell_measurement_theta_min      1.97
_cell_volume                     2011.7(7)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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 0.986
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      ' 132 frames, detector distance = 70 mm   '
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1181
_diffrn_reflns_av_unetI/netI     0.1609
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9173
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.230
_diffrn_reflns_theta_min         2.314
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.124
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.762
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.597
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4813
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.597
_refine_ls_R_factor_all          0.4114
_refine_ls_R_factor_gt           0.2540
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.5643
_refine_ls_wR_factor_ref         0.6393
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1616
_reflns_number_total             4813
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b08320_si_003.cif
_cod_data_source_block           DBOV-DMEP
_cod_database_code               4127701
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.996
_shelx_res_checksum              12561
_shelx_hkl_checksum              25487
_shelx_fab_checksum              9410