Highly Diastereoselective Arylations of Substituted Piperidines
Stephanie Seel; Tobias Thaler; Keishi Takatsu; Cong Zhang; Hendrik Zipse; Bernd F. Straub; Peter Mayer; Paul Knochel; Journal of the American Chemical Society 133 (2011) 4774–4777; doi:10.1021/ja201008e

data_4105891
_publ_contact_author_address
;
Department Chemie
Ludwig-Maximilians Universit\"at
Butenandtstra\&se 5-13 (Haus F)
D-81377 M\"unchen
Bundesrepublik Deutschland
;
_publ_contact_author_email       paul.knochel@cup.uni-muenchen.de
_publ_contact_author_fax         '+49 089-2180-77680'
_publ_contact_author_name        'Paul Knochel'
_publ_section_title
;
 Highly Diastereoselective Arylations of Substituted Piperidines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4774
_journal_page_last               4777
_journal_paper_doi               10.1021/ja201008e
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'C20 H22 F3 N O2 S'
_chemical_formula_sum            'C20 H22 F3 N O2 S'
_chemical_formula_weight         397.455
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_author_name               'P. Mayer'
_audit_block_code                C20H22F3NO2S_oo010_knochel
_audit_creation_date
;
'Wed Jan 20 10:23:51 2010'
;
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_audit_update_record             20-Jan-10
_cell_angle_alpha                90.00
_cell_angle_beta                 98.366(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1552(5)
_cell_length_b                   11.7039(5)
_cell_length_c                   16.2918(8)
_cell_measurement_reflns_used    3082
_cell_measurement_temperature    243(2)
_cell_measurement_theta_max      26.2490
_cell_measurement_theta_min      4.2964
_cell_volume                     1915.76(16)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_structure_refinement
;
Sheldrick, G. M. (2008).
<i>Acta Cryst.</i> A<b>64</b>, 112--122.
;
_computing_structure_solution
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;
_diffrn_ambient_temperature      243(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega  -93.00   13.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2931  -77.0000 -150.0000 106

  2 omega  -27.00   92.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3869    0.0000 -180.0000 119

;
_diffrn_measurement_device       'CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'Oxford XCalibur'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0694199589
_diffrn_orient_matrix_UB_12      0.0064067868
_diffrn_orient_matrix_UB_13      0.0000527954
_diffrn_orient_matrix_UB_21      0.0048649669
_diffrn_orient_matrix_UB_22      -0.0325800772
_diffrn_orient_matrix_UB_23      0.0370229823
_diffrn_orient_matrix_UB_31      0.0117337839
_diffrn_orient_matrix_UB_32      0.0507578890
_diffrn_orient_matrix_UB_33      0.0237863294
_diffrn_radiation_collimation    '0.5 mm collimator'
_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  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0604
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7447
_diffrn_reflns_theta_full        26.33
_diffrn_reflns_theta_max         26.33
_diffrn_reflns_theta_min         4.30
_diffrn_source_current           40_mA
_diffrn_source_power             2.00_kW
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50_kV
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.37804(12)
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.881
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3883
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      0.881
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0432P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0840
_reflns_number_gt                2580
_reflns_number_total             3883
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja201008e_si_009.cif
_cod_data_source_block           oo010
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4105891