Chiral Phosphoramide-Catalyzed Enantioselective Addition of Allylic Trichlorosilanes to Aldehydes. Preparative Studies with Bidentate Phosphorus-Based Amides
Scott E. Denmark; Jiping Fu; Michael J. Lawler; Journal of Organic Chemistry 71 (2006) 1523–1536; doi:10.1021/jo052203h

data_4021501
_publ_section_title
;
 Chiral Phosphoramide-Catalyzed Enantioselective Addition of
 Allylic Trichlorosilanes to Aldehydes. Preparative
 Studies with Bidentate Phosphorus-Based Amides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1523
_journal_page_last               1536
_journal_paper_doi               10.1021/jo052203h
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C28 H29 Br O2'
_chemical_formula_sum            'C28 H29 Br O2'
_chemical_formula_weight         477.42
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
; 
2001-06-12   text and data added, srw 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.9036(13)
_cell_length_b                   17.011(4)
_cell_length_c                   23.974(5)
_cell_measurement_reflns_used    867
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      21.9
_cell_measurement_theta_min      2.4
_cell_volume                     2407.6(9)
_computing_cell_refinement       'SAINT V5 (Bruker, 1998)'
_computing_data_collection       'SMART V5 (Bruker, 1998)'
_computing_data_reduction        'SAINT V5 (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL V5 (Bruker, 1998)'
_computing_publication_material  'CIFTAB (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXTL V5 (Bruker, 1998)'
_computing_structure_solution    'SHELXTL V5 (Bruker, 1998)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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_reflns_av_R_equivalents  0.0830
_diffrn_reflns_av_sigmaI/netI    0.1051
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            16949
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         1.70
_diffrn_standards_decay_%        2.7
_diffrn_standards_interval_time  607
_diffrn_standards_number         176
_exptl_absorpt_coefficient_mu    1.729
_exptl_absorpt_correction_T_max  0.9387
_exptl_absorpt_correction_T_min  0.6720
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Bruker, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       acicular
_exptl_crystal_F_000             992
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
thin glass fiber with the (1 0 -1) scattering planes roughly normal 
to the spindle axis. 
;
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.002(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.900
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         4933
_refine_ls_number_restraints     108
_refine_ls_restrained_S_all      0.893
_refine_ls_R_factor_all          0.1110
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0221P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0606
_refine_ls_wR_factor_ref         0.0720
_reflns_number_gt                2793
_reflns_number_total             4933
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo052203hrom20051021_041338.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4021501