Oxidative Deaminations and Deisatinylations of Ugi-Azide and Ugi-3CR Products: A Two-Step MCR-Oxidation Protocol toward Functionalized α-Ketoamides and α-Ketotetrazoles.
Foley, Christopher; Shaw, Arthur; Hulme, Christopher; Organic letters 19 (2017) 2238–2241; doi:10.1021/acs.orglett.7b00710

data_1556035
_publ_section_title
;
 Oxidative Deaminations and Deisatinylations of Ugi-Azide and Ugi-3CR
 Products: A Two-Step MCR-Oxidation Protocol toward Functionalized
 \a-Ketoamides and \a-Ketotetrazoles.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2238
_journal_page_last               2241
_journal_paper_doi               10.1021/acs.orglett.7b00710
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C14 H16 N4 O'
_chemical_formula_sum            'C14 H16 N4 O'
_chemical_formula_weight         256.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-12-10
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.3230(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7378(3)
_cell_length_b                   6.7075(2)
_cell_length_c                   12.6395(5)
_cell_measurement_reflns_used    6131
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.12
_cell_measurement_theta_min      2.69
_cell_volume                     640.89(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7085
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.119
_diffrn_reflns_theta_min         1.649
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1034 before and 0.0281 after correction.
The Ratio of minimum to maximum transmission is 0.9022.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0459P)^2^+0.2367P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0883
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1474
_reflns_number_total             1524
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00710_si_003.cif
_cod_data_source_block           mo_cf376f1_0m
_cod_database_code               1556035
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H14c(0.5) H14b(0.5) H14a(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7), C1(H1), C5(H5), C4(H4), C2(H2), C3(H3)
3.b Idealised Me refined as rotating group:
 C13(H13b,H13c,H13a), C14(H14c,H14b,H14a)
;
_shelx_res_checksum              24262
_shelx_hkl_checksum              98854
_shelx_shelxl_version_number     2014/7
_olex2_submission_original_sample_id cf371.f1
_olex2_submission_special_instructions 'No special instructions were received'