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_4028474
_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         'C10 H3 Br2 Cl2 I N2 '
_chemical_formula_sum            'C10 H3 Br2 Cl2 I N2'
_chemical_formula_weight         508.74
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.773(1)
_cell_angle_beta                 101.424(1)
_cell_angle_gamma                111.340(1)
_cell_formula_units_Z            2
_cell_length_a                   6.8899(1)
_cell_length_b                   9.0638(1)
_cell_length_c                   11.7741(2)
_cell_measurement_reflns_used    45382
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      37.5974
_cell_measurement_theta_min      2.8596
_cell_volume                     668.341(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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 (Mo) x-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0752
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            65157
_diffrn_reflns_theta_full        36.66
_diffrn_reflns_theta_max         36.66
_diffrn_reflns_theta_min         2.87
_exptl_absorpt_coefficient_mu    8.750
_exptl_absorpt_correction_T_max  0.373
_exptl_absorpt_correction_T_min  0.253
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
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    2.528
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.2141
_exptl_crystal_size_mid          0.2035
_exptl_crystal_size_min          0.1735
_refine_diff_density_max         0.935
_refine_diff_density_min         -0.911
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.001(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         13261
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0282
_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^)+(0.0501P)^2^+0.1827P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0718
_reflns_number_gt                13039
_reflns_number_total             13261
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401255q_si_002.cif
_cod_data_source_block           bipyk1peak1
_cod_original_cell_volume        668.341(17)
_cod_original_formula_sum        'C10 H3 Br2 Cl2 I N2 '
_cod_database_code               4028474