A Heterocycle-Forming Double Michael Reaction. [5 + 1] Annulation Route to Highly Substituted and Functionalized Piperidines
Hughes, Freddie; Grossman, Robert B.; Organic Letters 3 (2001) 2911–; doi:10.1021/ol016395o

data_1507526
_publ_section_title
;
 A Heterocycle-Forming Double Michael Reaction. [5 + 1] Annulation Route
 to Highly Substituted and Functionalized Piperidines
;
_journal_issue                   18
_journal_name_full               'Organic Letters'
_journal_page_first              2911
_journal_paper_doi               10.1021/ol016395o
_journal_volume                  3
_journal_year                    2001
_chemical_formula_sum            'C20 H25 F3 N2 O8'
_chemical_formula_weight         478.42
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_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                 120.430(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   29.928(4)
_cell_length_b                   9.4450(10)
_cell_length_c                   18.951(3)
_cell_measurement_temperature    173(2)
_cell_volume                     4619.0(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7128
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_correction_T_min  0.9486
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4082
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0550P)^2^+4.9000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1301
_reflns_number_gt                3065
_reflns_number_total             4082
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol016395o_s2.cif
_cod_data_source_block           k00006
_cod_original_cell_volume        4619.0(11)
_cod_database_code               1507526