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_7116872
_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            'C20 H8 Cl2 F6'
_chemical_formula_weight         433.16
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date
; 
'Fri Aug 08 13:28:26 2014' 
;
_audit_creation_method
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) 
(compiled Jul 11 2012,15:38:31) 
;
_audit_update_record
;
2014-10-17 deposited with the CCDC.
2015-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                97.590(3)
_cell_angle_beta                 96.803(3)
_cell_angle_gamma                103.045(3)
_cell_formula_units_Z            3
_cell_length_a                   8.5128(3)
_cell_length_b                   11.4844(5)
_cell_length_c                   13.1495(5)
_cell_measurement_reflns_used    7255
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.4629
_cell_measurement_theta_min      3.4287
_cell_volume                     1226.68(9)
_computing_cell_refinement
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) 
(compiled Jul 11 2012,15:38:31) 
;
_computing_data_reduction
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) 
(compiled Jul 11 2012,15:38:31) 
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_details
; 
  1 omega   86.58  268.93   1.1997    6.0000 
omega____ theta____ kappa____ phi______ frames 
    -      113.0000   73.8669  219.2088 152 
  
  2 omega   84.15  238.91   1.1997    6.0000 
omega____ theta____ kappa____ phi______ frames 
    -      111.0000   73.8669   69.2094 129 
  
  3 phi    124.45  326.15   1.2006    6.0000 
omega____ theta____ kappa____ phi______ frames 
 161.4694  110.0000   73.8669     -     168 
  
  4 omega   94.08  246.48   1.2000    6.0000 
omega____ theta____ kappa____ phi______ frames 
    -      112.0000   73.8669    4.2094 127 
  
  5 omega  -62.04   57.96   1.2000    0.7200 
omega____ theta____ kappa____ phi______ frames 
    -      -45.0000   73.8669  289.2094 100 
  
  6 omega   83.89  190.66   1.1997    6.0000 
omega____ theta____ kappa____ phi______ frames 
    -      110.0000   73.8669  109.2094 89 
  
  7 phi    156.11  306.19   1.2006    3.0000 
omega____ theta____ kappa____ phi______ frames 
 111.2994  -40.0000   73.8669     -     125 
  
  8 omega  124.43  227.63   1.2000    6.0000 
omega____ theta____ kappa____ phi______ frames 
    -      110.0000   73.8669  314.2094 86 
  
  9 omega  -67.84   47.39   1.2003    3.0000 
omega____ theta____ kappa____ phi______ frames 
    -      -57.0000   73.8669   39.2088 96 
  
 10 omega  163.61  268.04   1.2003    6.0000 
omega____ theta____ kappa____ phi______ frames 
    -      112.0000   73.8669  149.2088 87 
  
 11 omega   94.28  169.88   1.2000    6.0000 
omega____ theta____ kappa____ phi______ frames 
    -      113.0000   73.8669  -25.7900 63 
  
 12 omega   55.01  128.21   1.2000    3.0000 
omega____ theta____ kappa____ phi______ frames 
    -       55.5000   73.8669  184.2094 61 
  
;
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \p scans'
_diffrn_orient_matrix_UB_11      -0.1621642000
_diffrn_orient_matrix_UB_12      -0.0339469000
_diffrn_orient_matrix_UB_13      -0.0754939000
_diffrn_orient_matrix_UB_21      -0.0408101000
_diffrn_orient_matrix_UB_22      -0.1261777000
_diffrn_orient_matrix_UB_23      0.0324232000
_diffrn_orient_matrix_UB_31      -0.0858978000
_diffrn_orient_matrix_UB_32      0.0491183000
_diffrn_orient_matrix_UB_33      0.0869269000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8880
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         74.63
_diffrn_reflns_theta_min         3.43
_exptl_absorpt_coefficient_mu    4.224
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) 
(compiled Jul 11 2012,15:38:31) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.759
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cuboid
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         4698
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0329
_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^)+(0.0462P)^2^+0.7853P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0865
_reflns_number_gt                4361
_reflns_number_total             4698
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc10132d2.cif
_cod_data_source_block           s4084na
_cod_original_cell_volume        1226.69(9)
_cod_database_code               7116872