Asymmetric modular synthesis of a semirigid dipeptide mimetic by cascade cycloaddition/ring rearrangement and borohydride reduction.
Pellegrino, Sara; Contini, Alessandro; Gelmi, Maria Luisa; Lo Presti, Leonardo; Soave, Raffaella; Erba, Emanuela; The Journal of organic chemistry 79 (2014) 3094–3102; doi:10.1021/jo500237j

data_4029249
_publ_section_title
;
 Asymmetric modular synthesis of a semirigid dipeptide mimetic by cascade
 cycloaddition/ring rearrangement and borohydride reduction.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3094
_journal_page_last               3102
_journal_paper_doi               10.1021/jo500237j
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H33 N3 O4 S'
_chemical_formula_sum            'C25 H33 N3 O4 S'
_chemical_formula_weight         471.60
_chemical_name_systematic
;
 ?
;
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             XXXXXXXXXXXXX
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.774(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.2959(9)
_cell_length_b                   21.648(3)
_cell_length_c                   9.8033(14)
_cell_measurement_reflns_used    5465
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.6
_cell_measurement_theta_min      2.4
_cell_volume                     1272.4(3)
_computing_cell_refinement
'SAINT+ (Bruker AXS, Madison (USA) 1994-1996)'
_computing_data_collection
'SAINT+ (Bruker AXS, Madison (USA) 1994-1996)'
_computing_data_reduction
'SAINT+ (Bruker AXS, Madison (USA) 1994-1996)'
_computing_molecular_graphics    'Diamond v3.2i (Brandenburg, 2012)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker AXS APEX CCD area-detector'
_diffrn_measurement_method       \w-scan
_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  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19930
_diffrn_reflns_theta_full        30.15
_diffrn_reflns_theta_max         30.15
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6782
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS-2007/4; Sheldrick, 2004'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     414
_refine_ls_number_reflns         7434
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0570P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.1011
_reflns_number_gt                5493
_reflns_number_total             7434
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500237j_si_002.cif
_cod_data_source_block           cf38
_cod_depositor_comments
;Adding full bibliography for
 ./tmp-cod-update-bibliographies-12971/cifs/4029249.cif.
;
_cod_original_cell_volume        1272.4(5)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4029249