Asymmetric synthesis of chloroisothreonine derivatives via syn-stereoselective Mannich-type additions across N-sulfinyl-α-chloroimines.
Callebaut, Gert; Colpaert, Filip; Nonn, Melinda; Kiss, Loránd; Sillanpää, Reijo; Törnroos, Karl W; Fülöp, Ferenc; De Kimpe, Norbert; Mangelinckx, Sven; Organic & biomolecular chemistry 12 (2014) 3393–3405; doi:10.1039/c4ob00243a

data_7153750
_publ_section_title
;
 Asymmetric synthesis of chloroisothreonine derivatives via
 syn-stereoselective Mannich-type additions across
 N-sulfinyl-\a-chloroimines.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3393
_journal_page_last               3405
_journal_paper_doi               10.1039/c4ob00243a
_journal_volume                  12
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H24 Cl N O4 S'
_chemical_formula_sum            'C12 H24 Cl N O4 S'
_chemical_formula_weight         313.83
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   9.4099(9)
_cell_length_b                   9.4099(9)
_cell_length_c                   31.116(3)
_cell_measurement_reflns_used    9653
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.48
_cell_measurement_theta_min      2.50
_cell_volume                     2386.1(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            41013
_diffrn_reflns_theta_full        31.48
_diffrn_reflns_theta_max         31.48
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    0.380
_exptl_absorpt_correction_T_max  0.8300
_exptl_absorpt_correction_T_min  0.8238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS G.M Sheldrick, University of 
G\"ttingen, Germany, 2008.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular prism'
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.51
_refine_diff_density_max         0.811
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.244
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         10576
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.244
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0319P)^2^+1.2559P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                10532
_reflns_number_total             10576
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00243a2.cif
_cod_data_source_block           Compound7ac
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 7153748--7153750.cif.
;
_cod_original_sg_symbol_H-M      P3(1)
_cod_database_code               7153750