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_4037603
_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         'C10 H4 Br2 I2 N2'
_chemical_formula_sum            'C10 H4 Br2 I2 N2'
_chemical_formula_weight         565.75
_chemical_name_systematic
;
'5,5'-Dibromo-3,3'-diiodo-[4,4']bipyridinyl'
;
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 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                102.6890(10)
_cell_angle_beta                 98.1530(10)
_cell_angle_gamma                90.8930(10)
_cell_formula_units_Z            4
_cell_length_a                   8.07800(10)
_cell_length_b                   11.29930(10)
_cell_length_c                   15.5039(2)
_cell_measurement_reflns_used    56204
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      37.7010
_cell_measurement_theta_min      2.9237
_cell_volume                     1365.01(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Mova (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0752
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            106245
_diffrn_reflns_theta_full        36.65
_diffrn_reflns_theta_max         36.65
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    10.437
_exptl_absorpt_correction_T_max  0.491
_exptl_absorpt_correction_T_min  0.282
_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    2.753
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.1678
_exptl_crystal_size_mid          0.1499
_exptl_crystal_size_min          0.0796
_refine_diff_density_max         1.863
_refine_diff_density_min         -1.931
_refine_diff_density_rms         0.137
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.124(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     617
_refine_ls_number_reflns         27062
_refine_ls_number_restraints     105
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0228P)^2^+4.6175P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0707
_reflns_number_gt                25198
_reflns_number_total             27062
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300286z_si_003.cif
_cod_data_source_block           bipyapeak2
_cod_database_code               4037603