Spiro-fused pyrrolidine, piperidine, and oxindole scaffolds from lactams.
Hirschhäuser, Christoph; Parker, Jeremy S.; Perry, Matthew W. D.; Haddow, Mairi F.; Gallagher, Timothy; Organic letters 14 (2012) 4846–4849; doi:10.1021/ol302176z

data_1516060
_publ_section_title
;
 Spiro-fused pyrrolidine, piperidine, and oxindole scaffolds from lactams.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4846
_journal_page_last               4849
_journal_paper_doi               10.1021/ol302176z
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration uk
_chemical_formula_moiety         'C16 H20 N2 O3'
_chemical_formula_sum            'C16 H20 N2 O3'
_chemical_formula_weight         288.34
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   40.076(7)
_cell_length_b                   5.5575(11)
_cell_length_c                   13.021(2)
_cell_measurement_reflns_used    882
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      17.99
_cell_measurement_theta_min      2.57
_cell_volume                     2900.1(9)
_computing_cell_refinement       'Bruker Apex II'
_computing_data_collection       'Bruker Apex II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker ShelXTL'
_computing_publication_material  'Bruker ShelXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Apex II kappa 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  0.2227
_diffrn_reflns_av_sigmaI/netI    0.1420
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_h_min       -51
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26080
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_correction_T_min  0.7975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         3483
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.1450
_refine_ls_R_factor_gt           0.0533
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0317P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.1042
_reflns_number_gt                1847
_reflns_number_total             3483
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302176z_si_001.cif
_cod_data_source_block           10a
_cod_original_cell_volume        2899.9(9)
_cod_original_sg_symbol_H-M      Pna21
_cod_database_code               1516060