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_1514690
_publ_section_title
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 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         'C16 H23 N1 O2'
_chemical_formula_sum            'C16 H23 N O2'
_chemical_formula_weight         261.36
_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                75.311(7)
_cell_angle_beta                 80.306(9)
_cell_angle_gamma                71.263(10)
_cell_formula_units_Z            2
_cell_length_a                   8.7960(10)
_cell_length_b                   8.8679(7)
_cell_length_c                   10.3885(9)
_cell_measurement_reflns_used    4603
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.9348
_cell_measurement_theta_min      4.4162
_cell_volume                     738.95(13)
_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 0.988
_diffrn_measured_fraction_theta_max 0.978
_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  0.064
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8622
_diffrn_reflns_theta_full        66.220
_diffrn_reflns_theta_max         67.044
_diffrn_reflns_theta_min         4.420
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_T_max  0.899
_exptl_absorpt_correction_T_min  0.810
_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    1.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.523
_exptl_crystal_size_mid          0.347
_exptl_crystal_size_min          0.234
_refine_diff_density_max         0.78
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9627
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2587
_refine_ls_number_restraints     259
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0704
_refine_ls_shift/su_max          0.0007998
_refine_ls_shift/su_mean         0.0002275
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
0.265E+04 0.447E+04 0.269E+04 0.108E+04 229.
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1963
_refine_ls_wR_factor_gt          0.1905
_refine_ls_wR_factor_ref         0.1963
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              10
_reflns_limit_k_min              -9
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                2319
_reflns_number_total             2588
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.80
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0742
_oxford_refine_ls_scale          7.9(4)
_oxford_reflns_number_all        2587
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            c3sc50428j.txt
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C16 H23 N1 O2'
_cod_database_code               1514690
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S
RIDE C ( 3,X'S) H ( 31,X'S) H ( 32,X'S) H ( 33,X'S)
RIDE C ( 4,X'S) H ( 43,X'S) H ( 42,X'S) H ( 41,X'S)
RIDE C ( 5,X'S) H ( 53,X'S) H ( 52,X'S) H ( 51,X'S)
RIDE C ( 9,X'S) H ( 92,X'S) H ( 91,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 ( 182,X'S) H ( 181,X'S)
RIDE C ( 19,X'S) H ( 191,X'S) H ( 192,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)
REM SHIFTLIMIT START (DO NOT REMOVE THIS LINE)
LIMIT 0.01000000 U[ISO]
LIMIT 0.01000000 X
LIMIT 0.01000000 Y
LIMIT 0.01000000 Z
LIMIT 0.01000000 U[11]
LIMIT 0.01000000 U[22]
LIMIT 0.01000000 U[33]
LIMIT 0.01000000 U[12]
LIMIT 0.01000000 U[13]
LIMIT 0.01000000 U[23]
LIMIT 0.01000000 OCC
REM SHIFTLIMIT END (DO NOT REMOVE THIS LINE)
END
;