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_7116870
_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            'C54 H52'
_chemical_formula_weight         700.96
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.2582(6)
_cell_length_b                   14.2403(8)
_cell_length_c                   42.561(2)
_cell_measurement_reflns_used    4085
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.09
_cell_measurement_theta_min      3.73
_cell_volume                     8035.5(7)
_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 0.992
_diffrn_measured_fraction_theta_max 0.982
_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  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0550
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            23068
_diffrn_reflns_theta_full        66.60
_diffrn_reflns_theta_max         70.11
_diffrn_reflns_theta_min         3.27
_exptl_absorpt_coefficient_mu    0.487
_exptl_absorpt_correction_T_max  0.9855
_exptl_absorpt_correction_T_min  0.801691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             3008
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.9(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     977
_refine_ls_number_reflns         13704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0568P)^2^+0.7663P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1150
_reflns_number_gt                11325
_reflns_number_total             13704
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc10132d2.cif
_cod_data_source_block           s3937ma
_cod_original_cell_volume        8035.6(7)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7116870