Enantioselective C-h bond addition of pyridines to alkenes catalyzed by chiral half-sandwich rare-Earth complexes.
Song, Guoyong; O, Wylie W N; Hou, Zhaomin; Journal of the American Chemical Society 136 (2014) 12209–12212; doi:10.1021/ja504995f

data_4122477
_publ_section_title
;
 Enantioselective C-h bond addition of pyridines to alkenes catalyzed by
 chiral half-sandwich rare-Earth complexes.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12209
_journal_page_last               12212
_journal_paper_doi               10.1021/ja504995f
_journal_volume                  136
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H18 N, F6 P'
_chemical_formula_sum            'C13 H18 F6 N P'
_chemical_formula_weight         333.25
_chemical_name_systematic
; 
 ? 
;
_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            16
_cell_length_a                   8.234(2)
_cell_length_b                   19.756(5)
_cell_length_c                   36.5075(10)
_cell_measurement_reflns_used    113914
_cell_measurement_temperature    163(2)
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      3.14
_cell_volume                     5939(2)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b25'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b25 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b25'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      163(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Hybrid pixel array detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '3 kW sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0803
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            113914
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         3.14
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  0.9419
_exptl_absorpt_correction_T_min  0.9051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2752
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.933
_refine_diff_density_min         -0.894
_refine_diff_density_rms         0.110
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.471
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     768
_refine_ls_number_reflns         10496
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.477
_refine_ls_R_factor_all          0.1249
_refine_ls_R_factor_gt           0.1121
_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3264
_refine_ls_wR_factor_ref         0.3467
_reflns_number_gt                8671
_reflns_number_total             10496
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja504995f_si_001.cif
_cod_data_source_block           5a_HPF6
_cod_depositor_comments
;Adding full bibliography for 4122477.cif.

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               4122477