Ligand-controlled β-selective C(sp3)–H arylation of N-Boc-piperidines
Millet, Anthony; Larini, Paolo; Clot, Eric; Baudoin, Olivier; Chemical Science 4 (2013) 2241–; doi:10.1039/c3sc50428j

data_1514692
_publ_section_title
;
 Ligand-controlled \b-selective C(sp3)--H arylation of N-Boc-piperidines
;
_journal_issue                   5
_journal_name_full               'Chemical Science'
_journal_page_first              2241
_journal_paper_doi               10.1039/c3sc50428j
_journal_volume                  4
_journal_year                    2013
_chemical_formula_moiety         'C20 H29 N1 O2'
_chemical_formula_sum            'C20 H29 N O2'
_chemical_formula_weight         315.44
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                76.241(4)
_cell_angle_beta                 75.622(5)
_cell_angle_gamma                77.643(5)
_cell_formula_units_Z            4
_cell_length_a                   10.7367(8)
_cell_length_b                   11.1830(5)
_cell_length_c                   16.1060(7)
_cell_measurement_reflns_used    7389
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.9145
_cell_measurement_theta_min      2.8855
_cell_volume                     1794.66(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10.4678
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19429
_diffrn_reflns_theta_full        67.023
_diffrn_reflns_theta_max         67.023
_diffrn_reflns_theta_min         2.888
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.579
_exptl_absorpt_correction_T_max  0.869
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
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    1.167
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.285
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.29
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0246
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         6285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.0004078
_refine_ls_shift/su_mean         0.0000505
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.40P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1159
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1159
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              13
_reflns_limit_k_min              -12
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                5316
_reflns_number_total             6316
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.10
_oxford_diffrn_Wilson_scale      0.04
_oxford_refine_ls_r_factor_ref   0.0528
_oxford_refine_ls_scale          5.30(9)
_oxford_reflns_number_all        6285
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            c3sc50428j.txt
_cod_data_source_block           3
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C20 H29 N1 O2'
_cod_database_code               1514692
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S
RIDE C ( 5,X'S) H ( 51,X'S) H ( 53,X'S) H ( 52,X'S)
RIDE C ( 6,X'S) H ( 61,X'S) H ( 63,X'S) H ( 62,X'S)
RIDE C ( 7,X'S) H ( 71,X'S) H ( 72,X'S) H ( 73,X'S)
RIDE C ( 9,X'S) H ( 91,X'S) H ( 92,X'S)
RIDE C ( 10,X'S) H ( 101,X'S)
RIDE C ( 12,X'S) H ( 121,X'S)
RIDE C ( 13,X'S) H ( 131,X'S)
RIDE C ( 14,X'S) H ( 141,X'S)
RIDE C ( 15,X'S) H ( 151,X'S)
RIDE C ( 16,X'S) H ( 161,X'S)
RIDE C ( 17,X'S) H ( 172,X'S) H ( 171,X'S)
RIDE C ( 18,X'S) H ( 181,X'S)
RIDE C ( 19,X'S) H ( 191,X'S)
RIDE C ( 20,X'S) H ( 202,X'S) H ( 201,X'S)
RIDE C ( 21,X'S) H ( 212,X'S) H ( 211,X'S)
RIDE C ( 22,X'S) H ( 222,X'S) H ( 221,X'S)
RIDE C ( 23,X'S) H ( 232,X'S) H ( 231,X'S)
RIDE C ( 26,X'S) H ( 261,X'S) H ( 263,X'S) H ( 262,X'S)
RIDE C ( 27,X'S) H ( 271,X'S) H ( 273,X'S) H ( 272,X'S)
RIDE C ( 28,X'S) H ( 281,X'S) H ( 282,X'S) H ( 283,X'S)
RIDE C ( 32,X'S) H ( 321,X'S) H ( 322,X'S)
RIDE C ( 33,X'S) H ( 331,X'S)
RIDE C ( 35,X'S) H ( 351,X'S)
RIDE C ( 36,X'S) H ( 361,X'S)
RIDE C ( 37,X'S) H ( 371,X'S)
RIDE C ( 38,X'S) H ( 381,X'S)
RIDE C ( 39,X'S) H ( 391,X'S)
RIDE C ( 40,X'S) H ( 402,X'S) H ( 401,X'S)
RIDE C ( 41,X'S) H ( 411,X'S)
RIDE C ( 42,X'S) H ( 421,X'S)
RIDE C ( 43,X'S) H ( 432,X'S) H ( 431,X'S)
RIDE C ( 44,X'S) H ( 442,X'S) H ( 441,X'S)
RIDE C ( 45,X'S) H ( 452,X'S) H ( 451,X'S)
RIDE C ( 46,X'S) H ( 462,X'S) H ( 461,X'S)
END
;
_iucr_refine_instruction_details_restraints
;
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;