One-pot synthesis of functionalized piperid-4-ones: a four-component condensation.
Clarke, Paul A.; Zaytsev, Andrey V.; Morgan, Tyson W.; Whitwood, Adrian C.; Wilson, Claire; Organic letters 10 (2008) 2877–2880; doi:10.1021/ol801051g

data_1504760
_publ_section_title
;
 One-pot synthesis of functionalized piperid-4-ones: a four-component
 condensation.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              2877
_journal_page_last               2880
_journal_paper_doi               10.1021/ol801051g
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C26 H25 N O5 S'
_chemical_formula_weight         463.53
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   'geom, sp2 bound Me and OH from difmap'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.050(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.823(3)
_cell_length_b                   8.027(2)
_cell_length_c                   19.753(4)
_cell_measurement_reflns_used    1342
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      20.35
_cell_measurement_theta_min      2.85
_cell_volume                     2247.0(9)
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2000)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_publication_material  'enCIFer (CCDC, 2003); PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.881
_diffrn_measured_fraction_theta_max 0.832
_diffrn_measurement_device_type  'Bruker SMART1000 area detector diffractometer'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         ' sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_av_sigmaI/netI    0.0499
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10839
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.16
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Twinabs v2007/3'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         5548
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0611P)^2^+1.6084P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1268
_reflns_number_gt                4591
_reflns_number_total             5548
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol801051g-file005.cif
_cod_data_source_block           4a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1504760