Palladacycle-Catalyzed Triple Suzuki Coupling Strategy for the Synthesis of Anthracene-Based OLED Emitters.
Dhangar, Gopal; Serrano, Jose Luis; Schulzke, Carola; Gunturu, Krishna Chaitanya; Kapdi, Anant R.; ACS omega 2 (2017) 3144–3156; doi:10.1021/acsomega.7b00725

data_4516901
_publ_section_title
;
 Palladacycle-Catalyzed Triple Suzuki Coupling Strategy for the Synthesis
 of Anthracene-Based OLED Emitters.
;
_journal_issue                   7
_journal_name_full               'ACS omega'
_journal_page_first              3144
_journal_page_last               3156
_journal_paper_doi               10.1021/acsomega.7b00725
_journal_volume                  2
_journal_year                    2017
_chemical_formula_sum            'C30 H19 Br'
_chemical_formula_weight         459.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90.64(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.892(3)
_cell_length_b                   7.5837(15)
_cell_length_c                   17.555(4)
_cell_measurement_reflns_used    18789
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.3
_cell_measurement_theta_min      6.4
_cell_volume                     2115.6(8)
_computing_cell_refinement       'X-Area by STOE & Cie GmbH 2010'
_computing_data_collection       'X-Area by STOE & Cie GmbH 2010'
_computing_data_reduction        'X-Area by STOE & Cie GmbH 2010'
_computing_molecular_graphics    'XP Version 5.1 by Bruker AXS 1998'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2013)'
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'STOE IPDS2T'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0741
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17977
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.183
_diffrn_reflns_theta_min         2.320
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.958
_exptl_absorpt_correction_T_max  0.9591
_exptl_absorpt_correction_T_min  0.7581
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'face indexed'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_description       prism
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.439
_exptl_crystal_size_mid          0.366
_exptl_crystal_size_min          0.361
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4614
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.7412P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1173
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3318
_reflns_number_total             4614
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao7b00725_si_002.cif
_cod_data_source_block           GDB-194
_cod_original_cell_volume        2115.6(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4516901
_shelx_estimated_absorpt_t_min   0.480
_shelx_estimated_absorpt_t_max   0.538
_shelxl_version_number           2013-3
_shelx_res_checksum              7943
_shelx_hkl_checksum              13611