Predominant (S)-Enantioselective Inclusion of Aryl Methyl Sulfoxides by (S)-Isoleucyl-(S)-phenylglycines
Motohiro Akazome; Ai Doba; Shoji Matsumoto; Katsuyuki Ogura; Journal of Organic Chemistry 75 (2010) 660–665; doi:10.1021/jo902197k

data_4025186
_publ_section_title
;
 Predominant (S)-Enantioselective Inclusion of Aryl Methyl Sulfoxides by
 (S)-Isoleucyl-(S)-phenylglycines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              660
_journal_page_last               665
_journal_paper_doi               10.1021/jo902197k
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C21 H28 N2 O4 S'
_chemical_formula_weight         404.51
_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'
_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                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.683(2)
_cell_length_b                   16.352(6)
_cell_length_c                   22.299(9)
_cell_measurement_reflns_used    1015
_cell_measurement_temperature    173
_cell_measurement_theta_max      18.62
_cell_measurement_theta_min      3.01
_cell_volume                     2072.2(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0662
_diffrn_reflns_av_sigmaI/netI    0.0791
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7004
_diffrn_reflns_theta_full        21.39
_diffrn_reflns_theta_max         21.39
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  0.9945
_exptl_absorpt_correction_T_min  0.9262
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(15)
_refine_ls_extinction_coef       0.0022(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         2337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0293P)^2^+0.8037P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.1016
_reflns_number_gt                1848
_reflns_number_total             2337
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902197k_si_002.cif
_cod_data_source_block           akaz061p212121
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        2072.3(14)
_cod_database_code               4025186