Oxidation of diazenyl-protected N-heterocycles – a new entry to functionalized lactams
Petrović, Martina; Scarpi, Dina; Nieger, Martin; Jung, Nicole; Occhiato, Ernesto G.; Bräse, Stefan; RSC Adv. 7 (2017) 9461–; doi:10.1039/C6RA26546D

data_7227609
_publ_section_title
;
 Oxidation of diazenyl-protected N-heterocycles -- a new entry to
 functionalized lactams
;
_journal_issue                   16
_journal_name_full               'RSC Adv.'
_journal_page_first              9461
_journal_paper_doi               10.1039/C6RA26546D
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C14 H17 N3 O3'
_chemical_formula_sum            'C14 H17 N3 O3'
_chemical_formula_weight         275.30
_chemical_name_systematic
;
 ethyl (E)-4-((2-oxopiperidin-1-yl)diazenyl)benzoate
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-10-17 deposited with the CCDC.
2016-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.877(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      71.9
_cell_measurement_theta_min      3.1
_cell_volume                     1327.27(6)
_computing_cell_refinement       'APEX3 v2015.9-RC2 (Bruker AXS)'
_computing_data_collection       'APEX3 v2015.9-RC2 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    Shelxtl
_computing_publication_material  publCIF
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE with Photon100 detector'
_diffrn_measurement_method       'rotation in \f and \w, 1\%, shutterless'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20424
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.118
_diffrn_reflns_theta_min         3.024
_diffrn_source                   'INCOATEC microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.814
_exptl_absorpt_correction_T_max  0.9812
_exptl_absorpt_correction_T_min  0.8739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
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_exptl_crystal_description       plates
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0024(4)
_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   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2610
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0455P)^2^+0.4246P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0899
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2289
_reflns_number_total             2610
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra26546d2.cif
_cod_data_source_block           sb837_hy_compound_6c_1
_cod_database_code               7227609
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.895
_shelx_estimated_absorpt_t_max   0.984
_shelx_res_checksum              23549