Synthesis of Highly Enantioenriched Chiral α-Aminoorganotins via Diastereoselective Ring Opening of Chiral N-(Arenesulfonyl) 2-Tributylstannyloxazolidines
Vincent Coeffard; Erwan Le Grognec; Isabelle Beaudet; Michel Evain; Jean-Paul Quintard; Journal of Organic Chemistry 74 (2009) 5822–5838; doi:10.1021/jo900223k

data_4024736
_publ_section_title
;
Synthesis of Highly Enantioenriched Chiral \a-Aminoorganotins via
Diastereoselective Ring Opening of Chiral N-(Arenesulfonyl)
2-Tributylstannyloxazolidines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5822
_journal_page_last               5838
_journal_paper_doi               10.1021/jo900223k
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H40 N2 O5 S1 Sn1'
_chemical_formula_sum            'C27 H40 N2 O5 S Sn'
_chemical_formula_weight         623.4
_chemical_name_systematic        ' ?'
_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'
_audit_creation_method           'Jana2006 Version : 23/10/2008'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.5154(12)
_cell_length_b                   15.5547(17)
_cell_length_c                   49.389(5)
_cell_measurement_temperature    100
_cell_volume                     5773.6(13)
_computing_publication_material
'Jana2006 (Petricek, Dusek & Palatinus, 2006)'
_computing_structure_refinement
'Jana2006 (Petricek, Dusek & Palatinus, 2006)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type  'Nonius CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       64
_diffrn_reflns_limit_l_min       -63
_diffrn_reflns_number            40680
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    0.995
_exptl_absorpt_correction_T_max  0.9183
_exptl_absorpt_correction_T_min  0.647
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
'Jana2006  (Petricek, Dusek & Palatinus, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.4339
_exptl_crystal_description       plate
_exptl_crystal_F_000             2476
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.65
_refine_diff_density_min         -0.69
_refine_ls_abs_structure_details
'Jana2006 (Petricek, Dusek & Palatinus, 2006)'
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_gt    1.89
_refine_ls_goodness_of_fit_ref   1.90
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     649
_refine_ls_number_reflns         12723
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.0343
_refine_ls_shift/su_mean         0.0009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/(\s^2^(I)+0.001936I^2^)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1140
_reflns_number_gt                11674
_reflns_number_total             12723
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo900223k_si_003.cif
_cod_data_source_block           (I)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Gaussian' changed to 'gaussian'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_formula_sum        'C27 H40 N2 O5 S1 Sn1'
_cod_database_code               4024736