Direct Transformation of N-protected α,β-Unsaturated γ-Amino Amides into γ-Lactams through a Base Mediated Molecular Rearrangement.
Ganesh Kumar, Mothukuri; Veeresh, Kuruva; Nalawade, Sachin A.; Nithun, Raj V.; Gopi, Hosahudya N.; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b01936

data_4036043
_publ_section_title
;
 Direct Transformation of N-protected \a,\b-Unsaturated \g-Amino Amides
 into \g-Lactams through a Base Mediated Molecular Rearrangement.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b01936
_journal_year                    2019
_chemical_formula_moiety         'C17 H24 N2 O3'
_chemical_formula_sum            'C17 H24 N2 O3'
_chemical_formula_weight         304.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 110.4360(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.9637(5)
_cell_length_b                   11.3042(4)
_cell_length_c                   21.2771(9)
_cell_measurement_reflns_used    9936
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.65
_cell_measurement_theta_min      4.44
_cell_volume                     3372.6(2)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20711
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.641
_diffrn_reflns_theta_min         4.435
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       cylindershape
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         1.141
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 2638 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.56(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         5806
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      2.070
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0550
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2125
_refine_ls_wR_factor_ref         0.2128
_reflns_Friedel_coverage         0.848
_reflns_Friedel_fraction_full    0.921
_reflns_Friedel_fraction_max     0.944
_reflns_number_gt                5783
_reflns_number_total             5806
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01936_si_002.cif
_cod_data_source_block           2b
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4036043
_shelxl_version_number           2013-4
_shelx_res_checksum              19330
_shelx_hkl_checksum              26276