Pincer CNC bis-N-heterocyclic carbenes: robust ligands for palladium-catalysed Suzuki–Miyaura arylation of bromoanthracene and related substrates
Zende, V. M.; Schulzke, C.; Kapdi, A. R.; Organic Chemistry Frontiers 2 (2015) 1397–; doi:10.1039/C5QO00236B

data_1553177
_publ_section_title
;
 Pincer CNC bis-N-heterocyclic carbenes: robust ligands for
 palladium-catalysed Suzuki--Miyaura arylation of bromoanthracene and
 related substrates
;
_journal_issue                   10
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1397
_journal_paper_doi               10.1039/C5QO00236B
_journal_volume                  2
_journal_year                    2015
_chemical_formula_sum            'C25 H27 Br2 N5 O2'
_chemical_formula_weight         589.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-07-11 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                82.99(3)
_cell_angle_beta                 87.24(3)
_cell_angle_gamma                62.65(3)
_cell_formula_units_Z            2
_cell_length_a                   8.8674(18)
_cell_length_b                   9.3784(19)
_cell_length_c                   16.618(3)
_cell_measurement_reflns_used    7716
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      49.4
_cell_measurement_theta_min      6.9
_cell_volume                     1218.3(5)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.933
_diffrn_measured_fraction_theta_max 0.977
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_Laue_measured_fraction_full 0.933
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7716
_diffrn_reflns_point_group_measured_fraction_full 0.933
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         24.598
_diffrn_reflns_theta_min         3.431
_exptl_absorpt_coefficient_mu    3.360
_exptl_absorpt_correction_T_max  0.7637
_exptl_absorpt_correction_T_min  0.5814
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'face indexed'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_description       platelet
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.402
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.060
_refine_diff_density_max         1.132
_refine_diff_density_min         -0.909
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4006
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1128P)^2^+0.6185P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1482
_refine_ls_wR_factor_ref         0.1615
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3174
_reflns_number_total             4006
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5qo00236b2.cif
_cod_data_source_block           shelx
_cod_database_code               1553177
_shelxl_version_number           2013-3
_shelx_res_checksum              59157