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_1505380
_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_compound_source        'Frederic Douelle'
_chemical_formula_moiety         'C23 H24 I1 N3 O10 S1'
_chemical_formula_sum            'C23 H24 I N3 O10 S'
_chemical_formula_weight         661.43
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             07-02-12
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 91.6490(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2772(3)
_cell_length_b                   14.9744(3)
_cell_length_c                   13.9581(3)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    150
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     2773.97(10)
_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    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker SMART'
_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  0.030
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            36600
_diffrn_reflns_theta_full        28.416
_diffrn_reflns_theta_max         30.555
_diffrn_reflns_theta_min         1.995
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.287
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.58
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.10
_refine_diff_density_max         3.97
_refine_diff_density_min         -2.79
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9319
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         8080
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.000688
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 1.66P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1024
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1024
_reflns_limit_h_max              18
_reflns_limit_h_min              -18
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                5866
_reflns_number_total             8100
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.80
_oxford_diffrn_Wilson_scale      10.18
_oxford_refine_ls_scale          0.3337(3)
_oxford_structure_analysis_title 'mg7001 in P2(1)/c'
_cod_data_source_file            ol070482ksi20070225_103715.cif
_cod_data_source_block           MG7001
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      'P 1 21/c 1 '
_cod_original_formula_sum        'C23 H24 I1 N3 O10 S1'
_cod_database_code               1505380