Annulated diketopiperazines from dipeptides or Schöllkopf reagents via tandem cyclization-intramolecular N-arylation.
Lim, Hwan Jung; Gallucci, Judith C.; RajanBabu, T. V.; Organic letters 12 (2010) 2162–2165; doi:10.1021/ol100663y

data_1502971
_publ_section_title
;
 Annulated diketopiperazines from dipeptides or Sch\"ollkopf reagents via
 tandem cyclization-intramolecular N-arylation.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2162
_journal_page_last               2165
_journal_paper_doi               10.1021/ol100663y
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C17 H18 Br1 N3 O2, H0.78 O0.39'
_chemical_formula_sum            'C17 H18.78 Br N3 O2.39'
_chemical_formula_weight         383.24
_chemical_name_common            'RajanBabu 1646'
_chemical_name_systematic        ?
_space_group_IT_number           145
_symmetry_cell_setting           trigonal
_symmetry_Int_Tables_number      145
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_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             2010-02-15T11:30:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   8.0855(1)
_cell_length_b                   8.0855(1)
_cell_length_c                   22.4109(2)
_cell_measurement_reflns_used    1960
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.037
_cell_measurement_wavelength     0.71073
_cell_volume                     1268.83(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.119279
_diffrn_orient_matrix_UB_12      0.783298E-1
_diffrn_orient_matrix_UB_13      0.56571E-2
_diffrn_orient_matrix_UB_21      0.608435E-1
_diffrn_orient_matrix_UB_22      0.462487E-1
_diffrn_orient_matrix_UB_23      -0.120641
_diffrn_orient_matrix_UB_31      -0.245339E-1
_diffrn_orient_matrix_UB_32      0.372228E-1
_diffrn_orient_matrix_UB_33      0.18963E-2
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.054
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            29488
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.73
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    2.446
_exptl_absorpt_correction_T_max  0.570
_exptl_absorpt_correction_T_min  0.477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'triangular chunk'
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.008(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3840
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.024
_refine_ls_R_factor_gt           0.0212
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0223P)^2^+0.3470P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0483
_refine_ls_wR_factor_ref         0.0494
_reflns_number_gt                3652
_reflns_number_total             3840
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100663y_si_001.cif
_cod_data_source_block           RajanBabu1646
_cod_depositor_comments
;
 Marking attached hydrogen atoms.

 Antanas Vaitkus,
 2017-07-12
;
_cod_original_sg_symbol_Hall     P32
_cod_original_sg_symbol_H-M      P32
_cod_database_code               1502971