Synthesis of tetraarylpyridines by chemo-selective Suzuki-Miyaura reactions of 3,5-dibromo-2,6-dichloropyridine.
Reimann, Sebastian; Parpart, Silvio; Ehlers, Peter; Sharif, Muhammad; Spannenberg, Anke; Langer, Peter; Organic & biomolecular chemistry 13 (2015) 6832–6838; doi:10.1039/c5ob00866b

data_7154510
_publ_section_title
;
 Synthesis of tetraarylpyridines by chemo-selective Suzuki-Miyaura
 reactions of 3,5-dibromo-2,6-dichloropyridine.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6832
_journal_page_last               6838
_journal_paper_doi               10.1039/c5ob00866b
_journal_volume                  13
_journal_year                    2015
_chemical_formula_sum            'C12 H8 Br Cl2 N'
_chemical_formula_weight         317.00
_chemical_name_systematic
;
3-Bromo-2,6-dichloro-5-(4-tolyl)pyridine
;
_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
;
2015-04-28 deposited with the CCDC.
2015-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.2980(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.5770(3)
_cell_length_b                   10.7855(3)
_cell_length_c                   7.6172(2)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.77
_cell_measurement_theta_min      2.37
_cell_volume                     1170.10(5)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_data_reduction        SAINT
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa APEX II Duo'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0156
_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       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            23134
_diffrn_reflns_theta_full        28.79
_diffrn_reflns_theta_max         28.79
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    3.938
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         3049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0212
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0281P)^2^+0.6513P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0528
_refine_ls_wR_factor_ref         0.0547
_reflns_number_gt                2737
_reflns_number_total             3049
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob00866b2.cif
_cod_data_source_block           ax0229
_cod_depositor_comments
'Adding full bibliography for 7154509--7154510.cif.'
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7154510