Synthesis of Polyhalogenated 4,4'-Bipyridines via a Simple Dimerization Procedure
Mohamed Abboud; Victor Mamane; Emmanuel Aubert; Claude Lecomte; Yves Fort; Journal of Organic Chemistry 75 (2010) 3224–3231; doi:10.1021/jo100152e

data_4025411
_publ_contact_author_address
;Equipe Synth\`ese Organom\'etallique de R\'eactivit\'e (SOR)
Laboratoire SRSMC UMR CNRS-UHP 7565
Nancy-Universit\'e
Boulevard des Aiguillettes BP70239
54506 Vandoeuvre-l\`es-Nancy
France
;
_publ_contact_author_email       victor.mamane@sor.uhp-nancy.fr
_publ_contact_author_fax         '(33) 3 83 68 47 85'
_publ_contact_author_name        'Mamane, Victor'
_publ_contact_author_phone       '(33) 3 83 68 43 20'
_publ_section_title
;
 Synthesis of Polyhalogenated 4,4'-Bipyridines via a Simple Dimerization
 Procedure
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3224
_journal_page_last               3231
_journal_paper_doi               10.1021/jo100152e
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C10 H5 Br Cl2 N2'
_chemical_formula_sum            'C10 H5 Br Cl2 N2'
_chemical_formula_weight         303.97
_chemical_name_systematic
;
 3-Bromo-2,2'-dichloro-[4,4']bipyridinyl
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 107.738(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.3807(2)
_cell_length_b                   7.2933(3)
_cell_length_c                   10.2971(3)
_cell_measurement_reflns_used    4522
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      31.0166
_cell_measurement_theta_min      3.4720
_cell_volume                     527.94(3)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-92
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 10.4508
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_sigmaI/netI    0.151
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12691
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         3.48
_exptl_absorpt_coefficient_mu    4.362
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
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    1.912
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.1172
_exptl_crystal_size_mid          0.0851
_exptl_crystal_size_min          0.0157
_refine_diff_density_max         2.701
_refine_diff_density_min         -0.735
_refine_diff_density_rms         0.198
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.44(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1912
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0627
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0922P)^2^+4.4407P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1644
_refine_ls_wR_factor_ref         0.1759
_reflns_number_gt                1632
_reflns_number_total             1912
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100152e_si_003.cif
_cod_data_source_block           3h-ma151
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4025411