Understanding the Correlation of Structure and Selectivity in the Chiral-Phosphoramide-Catalyzed Enantioselective Allylation Reactions: Solution and Solid-State Structural Studies of Bisphosphoramide.SnCl4 Complexes
Scott E. Denmark; Jiping Fu; Journal of the American Chemical Society 125 (2003) 2208–2216; doi:10.1021/ja021280g

data_4113473
_publ_contact_author
;
Scott E. Denmark
University of Illinois
Department of Chemistry
Roger Adams Laboratory, Box 18-5
Urbana, Illinois  61801
USA
;
_publ_contact_author_email       sdenmark@uiuc.edu
_publ_contact_author_fax         '1  217 333-3984'
_publ_contact_author_phone       '1  217 333 0066'
_publ_section_title
;
 Understanding the Correlation of Structure and Selectivity in the
 Chiral-Phosphoramide-Catalyzed Enantioselective Allylation Reactions:
 Solution and Solid-State Structural Studies of Bisphosphoramide.SnCl4
 Complexes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2208
_journal_page_last               2216
_journal_paper_doi               10.1021/ja021280g
_journal_volume                  125
_journal_year                    2003
_chemical_formula_moiety         'C23 H44 CL4 N6 O2 P2 Sn1, H2 0'
_chemical_formula_sum            'C23 H46 Cl4 N6 O3 P2 Sn'
_chemical_formula_weight         777.09
_chemical_name_common            7d(SnCl4
_chemical_name_systematic
;
?
;
_space_group_IT_number           20
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
?
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.898(3)
_cell_length_b                   18.010(3)
_cell_length_c                   12.420(2)
_cell_measurement_reflns_used    963
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.0
_cell_measurement_theta_min      2.4
_cell_volume                     3332.4(10)
_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 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0806
_diffrn_reflns_av_sigmaI/netI    0.0945
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15641
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.77
_diffrn_standards_decay_%        4.2
_diffrn_standards_interval_time  731
_diffrn_standards_number         248
_exptl_absorpt_coefficient_mu    1.218
_exptl_absorpt_correction_T_max  0.9680
_exptl_absorpt_correction_T_min  0.8267
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Bruker, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_description       columnar
_exptl_crystal_F_000             1592
_exptl_crystal_preparation
;
The data crystal was mounted using oil (Parantone-N, Exxon) to a
thin glass fiber with the (0 0 1) scattering planes roughly normal
to the spindle axis.
;
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         4023
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      0.919
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.002
_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          0.0612
_refine_ls_wR_factor_ref         0.0679
_reflns_number_gt                2874
_reflns_number_total             4023
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja021280g_2.cif
_cod_data_source_block           p48na
_cod_original_cell_volume        3332.6(10)
_cod_original_sg_symbol_H-M      'C 2 2 21 '
_cod_database_code               4113473