Chiral Hexahalogenated 4,4'-Bipyridines.
Mamane, V.; Peluso, P.; Aubert, E.; Cossu, S.; Pale, P.; The Journal of organic chemistry 81 (2016) 4576–4587; doi:10.1021/acs.joc.6b00413

data_4036736
_publ_section_title
;
 Chiral Hexahalogenated 4,4'-Bipyridines.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4576
_journal_page_last               4587
_journal_paper_doi               10.1021/acs.joc.6b00413
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C10 H2 Br4 I2 N2'
_chemical_formula_sum            'C10 H2 Br4 I2 N2'
_chemical_formula_weight         723.58
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        '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            4
_cell_length_a                   7.997(2)
_cell_length_b                   11.722(2)
_cell_length_c                   16.948(3)
_cell_measurement_temperature    105(2)
_cell_volume                     1588.7(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      105(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  D8Venture
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_source         'high brilliance Incoatec Microfocus Source '
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_sigmaI/netI    0.1107
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            48146
_diffrn_reflns_theta_full        34.65
_diffrn_reflns_theta_max         34.65
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    14.003
_exptl_absorpt_correction_T_max  0.1661
_exptl_absorpt_correction_T_min  0.1064
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    3.025
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.763
_refine_diff_density_min         -2.536
_refine_diff_density_rms         0.181
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.016(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         6807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0231
_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^)+(0.0288P)^2^+0.8142P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0543
_refine_ls_wR_factor_ref         0.0551
_reflns_number_gt                6584
_reflns_number_total             6807
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00413_si_009.cif
_cod_data_source_block           hal11b_p1
_cod_original_cell_volume        1588.6(6)
_cod_database_code               4036736