Synthesis, resolution, and absolute configuration of chiral 4,4'-bipyridines.
Mamane, Victor; Aubert, Emmanuel; Peluso, Paola; Cossu, Sergio; The Journal of organic chemistry 77 (2012) 2579–2583; doi:10.1021/jo300286z

data_4037599
_publ_section_title
;
 Synthesis, resolution, and absolute configuration of chiral
 4,4'-bipyridines.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2579
_journal_page_last               2583
_journal_paper_doi               10.1021/jo300286z
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C22 H14 Br2 N2'
_chemical_formula_sum            'C22 H14 Br2 N2'
_chemical_formula_weight         466.15
_chemical_name_systematic
;
'3',5'-Dibromo-3,5-diphenyl-[4,4']bipyridinyl'
;
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.61130(10)
_cell_length_b                   12.44370(10)
_cell_length_c                   17.7610(2)
_cell_measurement_reflns_used    27573
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      76.3188
_cell_measurement_theta_min      3.5489
_cell_volume                     3671.31(6)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR_92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 10.4508
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0521
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            36076
_diffrn_reflns_theta_full        76.52
_diffrn_reflns_theta_max         76.52
_diffrn_reflns_theta_min         4.98
_exptl_absorpt_coefficient_mu    5.691
_exptl_absorpt_correction_T_max  0.614
_exptl_absorpt_correction_T_min  0.408
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.2272
_exptl_crystal_size_mid          0.1668
_exptl_crystal_size_min          0.1101
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3854
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0250
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+3.3601P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0676
_reflns_number_gt                3771
_reflns_number_total             3854
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300286z_si_002.cif
_cod_data_source_block           vm781
_cod_database_code               4037599