Diastereoselective synthesis of novel aza-diketopiperazines via a domino cyclohydrocarbonylation/addition process
Pierre Regenass; Jean-Francois Margathe; Andre Mann; Jean Suffert; Marcel Hibert; Nicolas Girard; Dominique Bonnet; Chem.Commun. 50 (2014) 9657–; doi:10.1039/C4cc03660C

data_7115483
_publ_section_title
;
 Diastereoselective synthesis of novel aza-diketopiperazines via a domino
 cyclohydrocarbonylation/addition process
;
_journal_name_full               Chem.Commun.
_journal_page_first              9657
_journal_paper_doi               10.1039/C4cc03660C
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H21 N3 O3'
_chemical_formula_sum            'C16 H21 N3 O3'
_chemical_formula_weight         303.36
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 101.369(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.6284(6)
_cell_length_b                   11.6932(6)
_cell_length_c                   25.7411(15)
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.67
_cell_measurement_theta_min      5.69
_cell_volume                     3136.3(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            13001
_diffrn_reflns_theta_full        66.67
_diffrn_reflns_theta_max         66.67
_diffrn_reflns_theta_min         5.69
_exptl_absorpt_coefficient_mu    0.735
_exptl_absorpt_correction_T_max  0.8375
_exptl_absorpt_correction_T_min  0.7574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.08(14)
_refine_ls_extinction_coef       0.0035(2)
_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   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     402
_refine_ls_number_reflns         4347
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0285
_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^)+(0.0418P)^2^+0.7289P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.0770
_reflns_number_gt                4276
_reflns_number_total             4347
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c4cc03660c3.cif
_cod_data_source_block           mhpr130206
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7115483