Preparation of new axially chiral bridged 2,2'-bipyridines and pyridyl monooxazolines (pymox). Evaluation in copper(I)-catalyzed enantioselective cyclopropanation.
Bouet, Alexis; Deguest, Geoffrey; Heller, Barbara; Papamicaël, Cyril; Dupas, Georges; Oudeyer, Sylvain; Marsais, Francis; Levacher, Vincent; Organic & biomolecular chemistry 5 (2007) 1397–1404; doi:10.1039/b701549f

data_7151103
_publ_section_title
;
 Preparation of new axially chiral bridged 2,2'-bipyridines and pyridyl
 monooxazolines (pymox). Evaluation in copper(I)-catalyzed
 enantioselective cyclopropanation.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1397
_journal_page_last               1404
_journal_paper_doi               10.1039/b701549f
_journal_volume                  5
_journal_year                    2007
_chemical_absolute_configuration syn
_chemical_formula_sum            'C27 H21 N3 O2'
_chemical_formula_weight         419.47
_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   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            12
_cell_length_a                   10.052(2)
_cell_length_b                   15.052(3)
_cell_length_c                   42.205(8)
_cell_measurement_reflns_used    all
_cell_measurement_temperature    200(2)
_cell_volume                     6386(2)
_computing_data_collection       STOE-X-AREA
_computing_molecular_graphics    XP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'STOE-IPDS II'
_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  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            62075
_diffrn_reflns_theta_full        23.00
_diffrn_reflns_theta_max         23.00
_diffrn_reflns_theta_min         1.44
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2640
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(18)
_refine_ls_extinction_coef       0.0085(8)
_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   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     832
_refine_ls_number_reflns         8869
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0684
_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^)+(0.1343P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1820
_refine_ls_wR_factor_ref         0.1931
_reflns_number_gt                6461
_reflns_number_total             8869
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b701549f.txt
_cod_data_source_block           ks466
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7151103