Substrate-Controlled and Organocatalytic Asymmetric Synthesis of Carbocyclic Amino Acid Dipeptide Mimetics
Stephen Hanessian; Dilip K. Maji; Subramaniyan Govindan; Riccardo Matera; Marina Tintelnot-Blomley; Journal of Organic Chemistry 75 (2010) 2861–2876; doi:10.1021/jo100017t

data_4025386
_publ_section_title
;
 Substrate-Controlled and Organocatalytic Asymmetric Synthesis of
 Carbocyclic Amino Acid Dipeptide Mimetics
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2861
_journal_page_last               2876
_journal_paper_doi               10.1021/jo100017t
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration rmad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_sum            'C12 H21 N O3'
_chemical_formula_weight         227.30
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.1780(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.83570(10)
_cell_length_b                   31.1808(6)
_cell_length_c                   8.5989(2)
_cell_measurement_reflns_used    3676
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.66
_cell_measurement_theta_min      2.83
_cell_volume                     1262.41(5)
_computing_cell_refinement       'SMART (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker AXS Smart 2K/Platform'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_av_sigmaI/netI    0.1269
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10285
_diffrn_reflns_theta_full        72.83
_diffrn_reflns_theta_max         72.83
_diffrn_reflns_theta_min         2.83
_diffrn_standards_decay_%        0.00
_diffrn_standards_number         94
_exptl_absorpt_coefficient_mu    0.690
_exptl_absorpt_correction_T_max  1.0500
_exptl_absorpt_correction_T_min  0.7900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick,1996)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), XXXX Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.6(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4661
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1172
_refine_ls_R_factor_gt           0.0631
_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^)+(0.0503P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1584
_reflns_number_gt                2649
_reflns_number_total             4661
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo100017t_si_004.cif
_cod_data_source_block           han379
_cod_depositor_comments
;
The following automatic conversions were performed:

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

'_geom_angle_publ_flag' value 'Y' changed to 'y'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (42
times).

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
the built-in table from CIF Core dictionary named 'cif_core.dic'
version 2.4.1 from 2010-06-29 (32 times).

'_geom_torsion_publ_flag'
value 'Y' changed to 'y' according to the built-in table from CIF
Core dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29
(48 times).

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025386