IBX-mediated oxidation of unactivated cyclic amines: application in highly diastereoselective oxidative Ugi-type and aza-Friedel-Crafts reactions.
de Graaff, C.; Bensch, L.; van Lint, Matthijs J.; Ruijter, E.; Orru, R. V. A.; Organic & biomolecular chemistry 13 (2015) 10108–10112; doi:10.1039/c5ob01519g

data_7154706
_publ_section_title
;
 IBX-mediated oxidation of unactivated cyclic amines: application in
 highly diastereoselective oxidative Ugi-type and aza-Friedel-Crafts
 reactions.
;
_journal_issue                   40
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10108
_journal_page_last               10112
_journal_paper_doi               10.1039/c5ob01519g
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C20 H24 N2 O3'
_chemical_formula_sum            'C20 H24 N2 O3'
_chemical_formula_weight         340.41
_chemical_melting_point          454(4)
_chemical_name_systematic
'(1 R,3a S,4 S,7 R,7a R)-2-benzoyl-N-(tert-butyl)-2,3,3a,4,7,7a-hexahydro-1H-4,7-epoxyisoindole-1-carboxamide'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   'fourier maps'
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-05-12 deposited with the CCDC.
2015-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.1190(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0781(3)
_cell_length_b                   15.5615(6)
_cell_length_c                   12.3439(5)
_cell_measurement_reflns_used    9845
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.65
_cell_measurement_theta_min      4.58
_cell_volume                     1736.85(11)
_computing_cell_refinement       'Bruker Saint v8.34A'
_computing_data_collection       'Bruker Saint v8.34A'
_computing_data_reduction        'Bruker Saint v8.34A'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker Prospector with APEX II'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25514
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        66.739
_diffrn_reflns_theta_max         66.739
_diffrn_reflns_theta_min         4.584
_diffrn_source                   'Incoatec Cu microsource'
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2008/1'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0028(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3045
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0342P)^2^+0.9332P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0817
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2952
_reflns_number_total             3045
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob01519g2.cif
_cod_data_source_block           mz048
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '450.0-458.5' was changed to '454(4)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7154706.cif.
;
_cod_database_code               7154706
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              51883