Highly diastereoselective synthesis of vicinal quaternary and tertiary stereocenters using the iodo-aldol cyclization.
Douelle, Frederic; Capes, Amy S.; Greaney, Michael F.; Organic letters 9 (2007) 1931–1934; doi:10.1021/ol070482k

data_1505379
_publ_section_title
;
 Highly diastereoselective synthesis of vicinal quaternary and tertiary
 stereocenters using the iodo-aldol cyclization.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              1931
_journal_page_last               1934
_journal_paper_doi               10.1021/ol070482k
_journal_volume                  9
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_compound_source        'F. Douelle'
_chemical_formula_moiety         'C21 H20 I1 N3 O10 S1'
_chemical_formula_sum            'C21 H20 I N3 O10 S'
_chemical_formula_weight         633.37
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             06-09-15
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   22.344(5)
_cell_length_b                   29.436(6)
_cell_length_c                   14.928(3)
_cell_measurement_reflns_used    7524
_cell_measurement_temperature    150
_cell_measurement_theta_max      57
_cell_measurement_theta_min      5
_cell_volume                     9818(4)
_computing_cell_refinement       'SAINT (Siemens ,1995)'
_computing_data_collection       'SMART (Siemens, 1993)'
_computing_data_reduction        'SAINT (Siemens ,1995)'
_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    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker SMART'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            119668
_diffrn_reflns_theta_full        27.810
_diffrn_reflns_theta_max         28.969
_diffrn_reflns_theta_min         1.780
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.450
_exptl_absorpt_correction_T_max  0.67
_exptl_absorpt_correction_T_min  0.47
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_description       block
_exptl_crystal_F_000             5056
_exptl_crystal_recrystallization_method
;
Recrystallised in hexane/EtOAc 3/1 using the "two vials technics"
;
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.28
_refine_diff_density_max         2.47
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_refine_ls_abs_structure_details 'Flack (1983), 2816 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.298(14)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9975
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         6043
_refine_ls_number_restraints     1
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_refine_ls_R_factor_gt           0.0295
_refine_ls_shift/su_max          0.001425
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 11.3 15.2 4.90 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0666
_refine_ls_wR_factor_gt          0.0627
_refine_ls_wR_factor_ref         0.0666
_reflns_limit_h_max              30
_reflns_limit_h_min              0
_reflns_limit_k_max              39
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              -19
_reflns_number_gt                5504
_reflns_number_total             6066
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          0.076960(9)
_oxford_structure_analysis_title 'mg6002 in Fdd2'
_cod_data_source_file            ol070482ksi20070225_103657.cif
_cod_data_source_block           'data_mg6002'
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        9819(3)
_cod_original_sg_symbol_H-M      'F d d 2 '
_cod_original_formula_sum        'C21 H20 I1 N3 O10 S1'
_cod_database_code               1505379