C–H arylation of triphenylene, naphthalene and related arenes using Pd/C
Collins, Karl D.; Honeker, Roman; Vásquez-Céspedes, Suhelen; Tang, Dan-Tam D.; Glorius, Frank; Chem. Sci. 6 (2015) 1816–; doi:10.1039/C4SC03051F

data_1518611
_publ_section_title
;
 C--H arylation of triphenylene, naphthalene and related arenes using Pd/C
;
_journal_issue                   3
_journal_name_full               'Chem. Sci.'
_journal_page_first              1816
_journal_paper_doi               10.1039/C4SC03051F
_journal_volume                  6
_journal_year                    2015
_chemical_formula_sum            'C24 H16'
_chemical_formula_weight         304.37
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-07-11 deposited with the CCDC.
2015-01-12 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.002(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.1157(9)
_cell_length_b                   5.7556(3)
_cell_length_c                   29.6669(11)
_cell_measurement_reflns_used    5626
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      0.88
_cell_volume                     3104.2(3)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.093
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            38915
_diffrn_reflns_theta_full        67.38
_diffrn_reflns_theta_max         67.38
_diffrn_reflns_theta_min         3.13
_exptl_absorpt_coefficient_mu    0.559
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_correction_T_min  0.9110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00100(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         5320
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0638P)^2^+1.1470P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1448
_reflns_number_gt                3678
_reflns_number_total             5320
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4sc03051f2.cif
_cod_data_source_block           glo7606
_cod_depositor_comments
'Adding full bibliography for 1518610--1518611.cif.'
_cod_original_cell_volume        3104.2(2)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1518611