Two-Step Route to Diverse N-Functionalized Peptidomimetic-like Isatins through an Oxidation/Intramolecular Oxidative-Amidation Cascade of Ugi Azide and Ugi Three-Component Reaction Products.
Foley, Christopher; Shaw, Arthur; Hulme, Christopher; Organic letters 18 (2016) 4904–4907; doi:10.1021/acs.orglett.6b02383

data_1555757
_publ_section_title
;
 Two-Step Route to Diverse N-Functionalized Peptidomimetic-like Isatins
 through an Oxidation/Intramolecular Oxidative-Amidation Cascade of Ugi
 Azide and Ugi Three-Component Reaction Products.
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_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4904
_journal_page_last               4907
_journal_paper_doi               10.1021/acs.orglett.6b02383
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C21 H22 N2 O3'
_chemical_formula_weight         350.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                75.507(2)
_cell_angle_beta                 77.927(2)
_cell_angle_gamma                82.204(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5529(4)
_cell_length_b                   9.1794(4)
_cell_length_c                   12.3004(5)
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      35.7485
_cell_measurement_theta_min      2.3003
_cell_volume                     910.75(7)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'Bruker Instrument Service v2011.2.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  Bruker_Kappa_Apex
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            79000
_diffrn_reflns_theta_full        33.73
_diffrn_reflns_theta_max         37.24
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       equant
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.284
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         9109
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0462
_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^)+(0.0749P)^2^+0.2429P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1417
_reflns_number_gt                6564
_reflns_number_total             9109
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b02383_si_002.cif
_cod_data_source_block           I
_cod_database_code               1555757
_vrf
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PROBLEM: Long   C(sp2)-C(sp2) Bond  C1     -   C2     ...       1.55 Ang.
RESPONSE: C1 and C2 are bound to a carbonyl oxygen. Thus despite these two adjacent carbons being sp2 hybridized,
 only a single bonded is expected between them.
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