Chemoenzymatic synthesis of chiral 2,2'-bipyridine ligands and their N-oxide derivatives: applications in the asymmetric aminolysis of epoxides and asymmetric allylation of aldehydes.
Boyd, D. R.; Sharma, N. D.; Sbircea, L.; Murphy, D.; Malone, J. F.; James, S. L.; Allen, C. C. R.; Hamilton, J. T. G.; Organic & biomolecular chemistry 8 (2010) 1081–1090; doi:10.1039/b919894f

data_7153272
_publ_section_title
;
 Chemoenzymatic synthesis of chiral 2,2'-bipyridine ligands and their
 N-oxide derivatives: applications in the asymmetric aminolysis of
 epoxides and asymmetric allylation of aldehydes.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1081
_journal_page_last               1090
_journal_paper_doi               10.1039/b919894f
_journal_volume                  8
_journal_year                    2010
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C26 H32 N2 O6'
_chemical_formula_sum            'C26 H32 N2 O6'
_chemical_formula_weight         468.54
_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   difmap
_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                   14.1616(1)
_cell_length_b                   14.2969(1)
_cell_length_c                   22.8822(2)
_cell_measurement_reflns_used    101809
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     4632.89(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        'Denzo & Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       KappaCCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            66883
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'sortav (Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.809
_refine_diff_density_rms         0.145
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(8)
_refine_ls_extinction_coef       0.0179(11)
_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   1.155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     656
_refine_ls_number_reflns         10614
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0601P)^2^+3.7018P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1431
_refine_ls_wR_factor_ref         0.1461
_reflns_number_gt                10001
_reflns_number_total             10614
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b919894f.txt
_cod_data_source_block           3Jp
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7153272