An orthogonal C-H borylation - cross-coupling strategy for the preparation of tetrasubstituted 'A2B2'-chrysene derivatives with tuneable photophysical properties
K. W. J. Heard; J. J. Morrison; L. Weston; C. H. Lo; L. Pirvu; J. Raftery; M. S. Little; J. J. W. McDouall; S. G. Yeates; P. Quayle; Chem.Commun. 51 (2015) 6115–; doi:10.1039/C4cc10132D

data_7116871
_publ_section_title
;
 An orthogonal C-H borylation - cross-coupling strategy for the
 preparation of tetrasubstituted 'A2B2'-chrysene derivatives with tuneable
 photophysical properties
;
_journal_name_full               Chem.Commun.
_journal_page_first              6115
_journal_paper_doi               10.1039/C4cc10132D
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C42 H42 Cl2'
_chemical_formula_weight         617.66
_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
;
2014-10-17 deposited with the CCDC.
2015-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.615(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.5669(11)
_cell_length_b                   11.5716(8)
_cell_length_c                   18.0171(14)
_cell_measurement_reflns_used    9948
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.56
_cell_measurement_theta_min      2.86
_cell_volume                     3223.9(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0604
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27577
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         72.94
_diffrn_reflns_theta_min         2.86
_exptl_absorpt_coefficient_mu    2.020
_exptl_absorpt_correction_T_max  0.7792
_exptl_absorpt_correction_T_min  0.607457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         6250
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0611
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0847P)^2^+4.7058P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1708
_refine_ls_wR_factor_ref         0.1818
_reflns_number_gt                5224
_reflns_number_total             6250
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc10132d2.cif
_cod_data_source_block           s4067na
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7116871