Removal of the Pyridine Directing Group from α-Substituted N-(Pyridin-2-yl)piperidines Obtained via Directed Ru-Catalyzed sp3 C-H Functionalization
Veerle Smout; Aldo Peschiulli; Stefan Verbeeck; Emily A. Mitchell; Wouter Herrebout; Patrick Bultinck; Christophe M. L. Vande Velde; Didier Berthelot; Lieven Meerpoel; Bert U. W. Maes; Journal of Organic Chemistry 78 (2013) 9803–9814; doi:10.1021/jo401521y

data_4028635
_publ_section_title
;
 Removal of the Pyridine Directing Group from \a-Substituted
 N-(Pyridin-2-yl)piperidines Obtained via Directed Ru-Catalyzed sp3 C-H
 Functionalization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9803
_journal_page_last               9814
_journal_paper_doi               10.1021/jo401521y
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C10 H10 Cl0 N2 O2'
_chemical_formula_weight         190.20
_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            15
_cell_length_a                   7.4578(7)
_cell_length_b                   9.7077(8)
_cell_length_c                   50.505(4)
_cell_measurement_temperature    293(2)
_cell_volume                     3656.5(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.953
_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  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0568
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       66
_diffrn_reflns_limit_l_min       -73
_diffrn_reflns_number            29772
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         31.98
_diffrn_reflns_theta_min         0.81
_exptl_absorpt_coefficient_mu    0.092
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             1500
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.20(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         11850
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0519
_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^)+(0.0561P)^2^+0.8620P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1274
_reflns_number_gt                9847
_reflns_number_total             11850
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401521y_si_001.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        3656.5(6)
_cod_database_code               4028635