Allylic C-H Amination for the Preparation of syn-1,3-Amino Alcohol Motifs
Grant T. Rice; M. Christina White; Journal of the American Chemical Society 131 (2009) 11707–11711; doi:10.1021/ja9054959

data_4104914
_publ_contact_author
; 
Scott R. Wilson 
University of Illinois 
School of Chemical Sciences, Box 59-1 
505 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
;
_publ_contact_author_email       srwilson@uiuc.edu
_publ_contact_author_fax         '1  217 244 8068'
_publ_contact_author_phone       '1  217 244 1708'
_publ_section_title
;
 Allylic C-H Amination for the Preparation of syn-1,3-Amino Alcohol Motifs
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11707
_journal_page_last               11711
_journal_paper_doi               10.1021/ja9054959
_journal_volume                  131
_journal_year                    2009
_chemical_formula_moiety         'C16 H18 N2 O6 S'
_chemical_formula_sum            'C16 H18 N2 O6 S'
_chemical_formula_weight         366.38
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
; 
2008-10-01   text and data added, srw 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.802(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.100(4)
_cell_length_b                   12.199(4)
_cell_length_c                   10.354(3)
_cell_measurement_reflns_used    888
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.28
_cell_volume                     1651.0(9)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'SMART V5.625 (Bruker, 2001)'
_computing_data_reduction
; 
SAINT V7.23A, XPREP V2005/2, SADABS V2007/4 (Bruker, 2005 & 2007) 
;
_computing_molecular_graphics    'SHELXTL V6.12 (Bruker, 2005)'
_computing_publication_material  'XCIF V6.12 (Bruker, 2005)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2005)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Siemens Platform/CCD'
_diffrn_measurement_method       'profile data from \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  b11dasx
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17388
_diffrn_reflns_theta_full        25.42
_diffrn_reflns_theta_max         25.42
_diffrn_reflns_theta_min         1.56
_diffrn_standards_decay_%        3.1
_diffrn_standards_interval_time  306
_diffrn_standards_number         144
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.9807
_exptl_absorpt_correction_T_min  0.9342
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP V2005/2 (Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_description       tabular
_exptl_crystal_F_000             768
_exptl_crystal_id                b11dasx
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (1 1 -1) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3054
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0663P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                2203
_reflns_number_total             3054
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9054959_si_003.cif
_cod_data_source_block           b11dasx
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               4104914