Synthesis of mono- and di-arylated acenaphthylenes and programmed access to dibenzo[j,l]fluoranthenes via palladium-catalysed C‒H bond functionalisation
Shi, Xinzhe; Roisnel, Thierry; Soulé, Jean-François; Doucet, Henri; Organic Chemistry Frontiers 5 (2018) 398–; doi:10.1039/C7QO00799J

data_1553903
_publ_section_title
;
 Synthesis of mono- and di-arylated acenaphthylenes and programmed access
 to dibenzo[j,l]fluoranthenes via palladium-catalysed C--H bond
 functionalisation
;
_journal_issue                   3
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              398
_journal_paper_doi               10.1039/C7QO00799J
_journal_volume                  5
_journal_year                    2018
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C24 H13 F'
_chemical_formula_sum            'C24 H13 F'
_chemical_formula_weight         320.34
_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'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2017-06-02 deposited with the CCDC.
2017-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.086(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4684(7)
_cell_length_b                   7.4280(4)
_cell_length_c                   18.7773(11)
_cell_measurement_reflns_used    3463
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.95
_cell_measurement_wavelength     0.71073
_cell_volume                     1460.11(15)
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2017)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12886
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.363
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0647
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0668P)^2^+1.5977P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1592
_refine_ls_wR_factor_ref         0.1789
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2348
_reflns_number_total             3338
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7qo00799j2.cif
_cod_data_source_block           SX2_556P
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1553903
_shelx_res_checksum              19261
_shelx_hkl_checksum              6195