Asymmetric Vinylogous Aldol Reaction of Silyloxy Furans with a Chiral Organic Salt
Ravi P. Singh; Bruce M. Foxman; Li Deng; Journal of the American Chemical Society 132 (2010) 9558–9560; doi:10.1021/ja103331t

data_4102672
_publ_section_title
;
 Asymmetric Vinylogous Aldol Reaction of Silyloxy Furans with a Chiral
 Organic Salt
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9558
_journal_page_last               9560
_journal_paper_doi               10.1021/ja103331t
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C36.57 H36.28 Cl1 F6 N4 O4.57 S1'
_chemical_formula_sum            'C36.57 H36.28 Cl F6 N4 O4.57 S'
_chemical_formula_weight         786.49
_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
_audit_creation_date             08-09-10
_audit_creation_method           CRYSTALS_ver_12.86
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6183(3)
_cell_length_b                   18.1350(7)
_cell_length_c                   24.0380(10)
_cell_measurement_reflns_used    3589
_cell_measurement_temperature    120
_cell_measurement_theta_max      20
_cell_measurement_theta_min      3
_cell_volume                     3757.0(3)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker Kappa Apex2'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.069
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            24579
_diffrn_reflns_theta_full        23.277
_diffrn_reflns_theta_max         23.277
_diffrn_reflns_theta_min         1.407
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Apex2 (Bruker AXS, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1629.095
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.68
_refine_diff_density_min         -0.64
_refine_ls_abs_structure_details 'Flack (1983), 2329 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.03(10)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         5414
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.001045
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 4.03P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1057
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.1057
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                3597
_reflns_number_total             5414
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.68
_oxford_diffrn_Wilson_scale      71.76
_oxford_refine_ls_r_factor_ref   0.0911
_oxford_refine_ls_scale          0.12899(5)
_oxford_reflns_number_all        5414
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'RPS_III_115_A_0m in P2(1)2(1)2(1)'
_cod_data_source_file            ja103331t_si_002.cif
_cod_data_source_block           RPS_III_115A
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C36.57 H36.28 Cl1 F6 N4 O4.57 S1'
_cod_database_code               4102672