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_1553904
_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 H14 Cl2'
_chemical_formula_sum            'C24 H14 Cl2'
_chemical_formula_weight         373.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 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                 114.382(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.8237(12)
_cell_length_b                   11.3330(7)
_cell_length_c                   10.2994(8)
_cell_measurement_reflns_used    2532
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.65
_cell_measurement_wavelength     0.71073
_cell_volume                     1788.6(2)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (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                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4736
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         3.479
_exptl_absorpt_coefficient_mu    0.367
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_correction_T_min  0.838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+1.4346P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0889
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1756
_reflns_number_total             2048
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7qo00799j2.cif
_cod_data_source_block           SX25_SP2
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1553904
_shelx_res_checksum              73331
_shelx_hkl_checksum              45894