Asymmetric conjugate reductions with samarium diiodide: asymmetric synthesis of (2S,3R)- and (2S,3S)-[2-2H,3-2H]-leucine-(S)-phenylalanine dipeptides and (2S,3R)-[2-(2)H,3-2H]-phenylalanine methyl ester.
Davies, Stephen G.; Rodriguez-Solla, Humberto; Tamayo, Juan A.; Cowley, Andrew R.; Concellon, Carmen; Garner, A. Christopher; Parkes, Alastair L.; Smith, Andrew D.; Organic & biomolecular chemistry 3 (2005) 1435–1447; doi:10.1039/b500566c

data_7150143
_publ_section_title
;
 Asymmetric conjugate reductions with samarium diiodide: asymmetric
 synthesis of (2S,3R)- and
 (2S,3S)-[2-2H,3-2H]-leucine-(S)-phenylalanine dipeptides and
 (2S,3R)-[2-(2)H,3-2H]-phenylalanine methyl ester.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1435
_journal_page_last               1447
_journal_paper_doi               10.1039/b500566c
_journal_volume                  3
_journal_year                    2005
_chemical_absolute_configuration syn
_chemical_compound_source
;
synthesis as described
;
_chemical_formula_moiety         ' C27 H34 N2 O4 '
_chemical_formula_sum            'C27 H34 N2 O4'
_chemical_formula_weight         450.58
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             01-11-10
_audit_creation_method           CRYSTALS_ver_12-03-99
_cell_angle_alpha                90
_cell_angle_beta                 110.9299(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.3830(4)
_cell_length_b                   7.0716(2)
_cell_length_c                   13.9236(5)
_cell_measurement_reflns_used    14684
_cell_measurement_temperature    150
_cell_measurement_theta_max      28
_cell_measurement_theta_min      5
_cell_volume                     1230.77(7)
_computing_cell_refinement
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_data_collection
;
KappaCCD software 'Collect' (Nonius, 2000)
;
_computing_data_reduction
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_publication_material
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_refinement
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
;
Nonius KappaCCD
;
_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       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14684
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         5.26
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_crystal_colour            ' colourless '
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_description       ' fragment '
_exptl_crystal_F_000             484.115
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.12
_refine_diff_density_min         -0.15
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0513
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         2510
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.004749
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Chebychev polynomial with 3 parameters (Carruthers & Watkin , 1979)
0.536    0.145    0.215
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0354
_reflns_limit_h_max              16
_reflns_limit_h_min              -17
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                2510
_reflns_number_total             2996
_reflns_threshold_expression     >3.00\s(I)
_cod_data_source_file            b500566c.txt
_cod_data_source_block           CRYSTALS_cif
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        1230.8
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_original_formula_sum        ' C27 H34 N2 O4 '
_cod_database_code               7150143