Asymmetric Sulfur Ylide Reactions with Boranes: Scope and Limitations, Mechanism and Understanding
Guang Y. Fang; Olov A. Wallner; Nadia Di Blasio; Xavier Ginesta; Jeremy N. Harvey; Varinder K. Aggarwal; Journal of the American Chemical Society 129 (2007) 14632–14639; doi:10.1021/ja074110i

data_4110201
_publ_section_title
;
 Asymmetric Sulfur Ylide Reactions with Boranes: Scope and Limitations,
 Mechanism and Understanding
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14632
_journal_page_last               14639
_journal_paper_doi               10.1021/ja074110i
_journal_volume                  129
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H21 Br O2'
_chemical_formula_sum            'C15 H21 Br O2'
_chemical_formula_weight         313.23
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.890(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.57920(10)
_cell_length_b                   9.1278(3)
_cell_length_c                   13.4765(3)
_cell_measurement_reflns_used    10932
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     682.68(3)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'SHELXTL v6.14 (Bruker-AXS, 2000)'
_computing_publication_material  'SHELXTL v6.14 (Bruker-AXS, 2000)'
_computing_structure_refinement  'SHELXTL v6.14 (Bruker-AXS, 2000)'
_computing_structure_solution    'SHELXTL v6.14 (Bruker-AXS, 2000)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker-Nonius APEX II CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10718
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         3.04
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    3.003
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    none
_exptl_crystal_description       needle
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack (1983), 1070 Friedel pairs'
_refine_ls_abs_structure_Flack   0.136(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.819
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2734
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.819
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0280
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0971
_reflns_number_gt                2619
_reflns_number_total             2734
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ja074110isi20070913_064714.cif
_cod_data_source_block           fg521
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4110201