Lithiation of Prochiral 2,2'-Dichloro-5,5'-dibromo-4,4'-bipyridine as a Tool for the Synthesis of Chiral Polyhalogenated 4,4'-Bipyridines
Victor Mamane; Emmanuel Aubert; Paola Peluso; Sergio Cossu; Journal of Organic Chemistry 78 (2013) 7683–7689; doi:10.1021/jo401255q

data_4028477
_publ_section_title
;
 Lithiation of Prochiral 2,2'-Dichloro-5,5'-dibromo-4,4'-bipyridine as a
 Tool for the Synthesis of Chiral Polyhalogenated 4,4'-Bipyridines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7683
_journal_page_last               7689
_journal_paper_doi               10.1021/jo401255q
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C13 H12 Br2 Cl2 N2 Sn'
_chemical_formula_sum            'C13 H12 Br2 Cl2 N2 Sn'
_chemical_formula_weight         545.66
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_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                   9.36000(10)
_cell_length_b                   14.37080(10)
_cell_length_c                   26.1227(2)
_cell_measurement_reflns_used    29686
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      76.4929
_cell_measurement_theta_min      3.0725
_cell_volume                     3513.78(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_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       'omega scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) x-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            33415
_diffrn_reflns_theta_full        76.69
_diffrn_reflns_theta_max         76.69
_diffrn_reflns_theta_min         3.38
_exptl_absorpt_coefficient_mu    19.641
_exptl_absorpt_correction_T_max  0.202
_exptl_absorpt_correction_T_min  0.043
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
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    2.063
_exptl_crystal_description       prism
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.3417
_exptl_crystal_size_mid          0.2364
_exptl_crystal_size_min          0.2099
_refine_diff_density_max         1.948
_refine_diff_density_min         -1.222
_refine_diff_density_rms         0.144
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.002(4)
_refine_ls_extinction_coef       0.00054(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         7378
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0302
_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^)+(0.0541P)^2^+6.5494P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0796
_reflns_number_gt                7367
_reflns_number_total             7378
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401255q_si_005.cif
_cod_data_source_block           bipyk7peak2
_cod_database_code               4028477