Formal [4+1] annulation of alpha,alpha-dialkyl beta-oxo amides and dimethylsulfoxonium methylide: a synthetic route to beta-hydroxy-gamma-lactams
Dingyuan Zhang; Qian Zhang; Ning Zhang; Rui Zhang; Yongjiu Liang; Dewen Dong; Chem.Commun. 49 (2013) 7358–; doi:10.1039/c3cc43317j

data_7109618
_publ_section_title
;
 Formal [4+1] annulation of alpha,alpha-dialkyl beta-oxo amides and
 dimethylsulfoxonium methylide: a synthetic route to
 beta-hydroxy-gamma-lactams
;
_journal_name_full               Chem.Commun.
_journal_page_first              7358
_journal_paper_doi               10.1039/c3cc43317j
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C13 H17 N O2'
_chemical_formula_weight         219.28
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 122.398(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.590(5)
_cell_length_b                   6.6126(16)
_cell_length_c                   19.413(5)
_cell_measurement_temperature    273(2)
_cell_volume                     2448.5(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7449
_diffrn_reflns_theta_full        26.03
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0582P)^2^+0.7252P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1264
_reflns_number_gt                1737
_reflns_number_total             2403
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc43317j.txt
_cod_data_source_block           11111
_cod_original_sg_symbol_H-M      C2/C
_cod_database_code               7109618