Functionalized Pyridylboronic Acids and Their Suzuki Cross-Coupling Reactions To Yield Novel Heteroarylpyridines
Paul R. Parry; Changsheng Wang; Andrei S. Batsanov; Martin R. Bryce; Brian Tarbit; Journal of Organic Chemistry 67 (2002) 7541–7543; doi:10.1021/jo020388b

data_4022213
_publ_contact_author             'Andrei S.Batsanov'
_publ_contact_author_email       a.s.batsanov@durham.ac.uk
_publ_section_title
;
 Functionalized Pyridylboronic Acids and Their Suzuki
 Cross-Coupling Reactions To Yield Novel Heteroarylpyridines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7541
_journal_page_last               7543
_journal_paper_doi               10.1021/jo020388b
_journal_volume                  67
_journal_year                    2002
_chemical_formula_sum            'C5 H5 B Br N O2'
_chemical_formula_weight         201.82
_chemical_melting_point          441.1(10)
_chemical_name_systematic
;
  2-bromo-5-pyridine boronoc acid   
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.81(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.535(2)
_cell_length_b                   6.941(1)
_cell_length_c                   13.877(3)
_cell_measurement_reflns_used    515
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      22.5
_cell_measurement_theta_min      12.0
_cell_volume                     720.7(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'SMART 1K CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6245
_diffrn_reflns_theta_full        29.12
_diffrn_reflns_theta_max         29.12
_diffrn_reflns_theta_min         2.72
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    5.635
_exptl_absorpt_correction_T_max  0.6639
_exptl_absorpt_correction_T_min  0.2191
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
'XPREP (SHELXTL) program; before correction R(int)=0.163'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.860
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'diamond plate'
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1913
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0360P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0824
_reflns_number_gt                1314
_reflns_number_total             1913
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo020388b_2.cif
_cod_data_source_block           2a(RT)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '167--168.9\% C' was changed to
'441.1(10)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4022213