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_4113474
_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_absolute_configuration syn
_chemical_formula_moiety         'C22 H42 Cl4 N6 O2 P2 Sn, 4(C H Cl3)'
_chemical_formula_sum            'C26 H46 Cl16 N6 O2 P2 Sn'
_chemical_formula_weight         1222.52
_chemical_name_common            7c(SnCl4
_chemical_name_systematic
;
?
;
_space_group_IT_number           144
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 31'
_symmetry_space_group_name_H-M   'P 31'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2002-10-08   text and data added, srw
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            3
_cell_length_a                   10.332(2)
_cell_length_b                   10.332(2)
_cell_length_c                   39.809(16)
_cell_measurement_reflns_used    959
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      23.17
_cell_measurement_theta_min      2.75
_cell_volume                     3680.3(18)
_computing_cell_refinement       'SAINT V6 (Bruker, 2001)'
_computing_data_collection       'SMART V5 (Bruker, 2001)'
_computing_data_reduction        'SAINT V6 (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL V6 (Bruker, 2001)'
_computing_publication_material  'CIFTAB (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXTL V6 (Bruker, 2001)'
_computing_structure_solution    'SHELXTL V6 (Bruker, 2001)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  p39qas
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_sigmaI/netI    0.0737
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            18194
_diffrn_reflns_theta_full        25.37
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         1.53
_diffrn_standards_decay_%        0.2
_diffrn_standards_interval_time  226
_diffrn_standards_number         442
_exptl_absorpt_coefficient_mu    1.491
_exptl_absorpt_correction_T_max  0.8648
_exptl_absorpt_correction_T_min  0.5359
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_description       tabular
_exptl_crystal_F_000             1836
_exptl_crystal_id                p39qas
_exptl_crystal_preparation
;
The data crystal was mounted using oil (Parantone-N, Exxon) to a
0.4 mm cryo-loop (Hampton Research) with the (1 1 0) scattering planes
roughly normal to the spindle axis.
;
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.10
_refine_diff_density_max         2.918
_refine_diff_density_min         -1.754
_refine_diff_density_rms         0.224
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.13(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     479
_refine_ls_number_reflns         7630
_refine_ls_number_restraints     590
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0948
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1363P)^2^+51.3723P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2553
_refine_ls_wR_factor_ref         0.2593
_reflns_number_gt                7045
_reflns_number_total             7630
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja021280g_3.cif
_cod_data_source_block           p39qas
_cod_original_cell_volume        3680.4(19)
_cod_original_sg_symbol_Hall     'P 31 '
_cod_original_sg_symbol_H-M      'P 31 '
_cod_database_code               4113474