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_1514691
_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         'C24 H28 F3 N1 O2'
_chemical_formula_sum            'C24 H28 F3 N O2'
_chemical_formula_weight         419.49
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 96.101(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7796(3)
_cell_length_b                   10.0791(3)
_cell_length_c                   21.9689(5)
_cell_measurement_reflns_used    12477
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.8900
_cell_measurement_theta_min      4.0120
_cell_volume                     2153.20(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
;
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.039
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            23974
_diffrn_reflns_theta_full        66.818
_diffrn_reflns_theta_max         66.818
_diffrn_reflns_theta_min         4.047
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  0.885
_exptl_absorpt_correction_T_min  0.711
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
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    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.679
_exptl_crystal_size_mid          0.327
_exptl_crystal_size_min          0.145
_refine_diff_density_max         0.47
_refine_diff_density_min         -0.34
_refine_ls_extinction_coef       33.2(12)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0227
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3806
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.0004979
_refine_ls_shift/su_mean         0.0000633
_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:
843. 0.133E+04 671. 175.
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0813
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0813
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                3589
_reflns_number_total             3806
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0424
_oxford_refine_ls_scale          4.84(6)
_oxford_reflns_number_all        3806
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            c3sc50428j.txt
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_original_formula_sum        'C24 H28 F3 N1 O2'
_cod_database_code               1514691
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S
CONT EXTPARAM
RIDE C ( 6,X'S) H ( 61,X'S)
RIDE C ( 7,X'S) H ( 71,X'S)
RIDE C ( 9,X'S) H ( 91,X'S)
RIDE C ( 10,X'S) H ( 101,X'S)
RIDE C ( 11,X'S) H ( 112,X'S) H ( 111,X'S)
RIDE C ( 12,X'S) H ( 121,X'S)
RIDE C ( 14,X'S) H ( 141,X'S) H ( 142,X'S)
RIDE C ( 19,X'S) H ( 191,X'S) H ( 192,X'S) H ( 193,X'S)
RIDE C ( 20,X'S) H ( 201,X'S) H ( 202,X'S) H ( 203,X'S)
RIDE C ( 21,X'S) H ( 212,X'S) H ( 211,X'S) H ( 213,X'S)
RIDE C ( 22,X'S) H ( 222,X'S) H ( 221,X'S) H ( 223,X'S)
RIDE C ( 24,X'S) H ( 241,X'S)
RIDE C ( 25,X'S) H ( 251,X'S)
RIDE C ( 26,X'S) H ( 261,X'S)
RIDE C ( 27,X'S) H ( 271,X'S)
RIDE C ( 28,X'S) H ( 281,X'S)
RIDE C ( 29,X'S) H ( 291,X'S)
RIDE C ( 30,X'S) H ( 301,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
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