Diastereoselective Synthesis of Diketopiperazine Bis-α,β-epoxides
Shin Ando; Amy L. Grote; Kazunori Koide; Journal of Organic Chemistry 76 (2011) 1155–1158; doi:10.1021/jo102096d

data_4026043
_publ_section_title
;
 Diastereoselective Synthesis of Diketopiperazine Bis-\a,\b-epoxides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1155
_journal_page_last               1158
_journal_paper_doi               10.1021/jo102096d
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C20 H18 N2 O4'
_chemical_formula_weight         350.36
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 91.927(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   14.326(4)
_cell_length_b                   15.140(4)
_cell_length_c                   24.246(6)
_cell_measurement_reflns_used    4794
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      26.07
_cell_measurement_theta_min      2.55
_cell_volume                     5256(2)
_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      203(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.937
_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  0.0598
_diffrn_reflns_av_sigmaI/netI    0.0577
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            32650
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         32.42
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9833
_exptl_absorpt_correction_T_min  0.9751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       anit-prism
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         8866
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0592
_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^)+(0.0780P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1663
_reflns_number_gt                5655
_reflns_number_total             8866
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102096d_si_002.cif
_cod_data_source_block           sa3036s
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4026043