Solvent-free double aza-Michael under ultrasound irradiation: diastereoselective sequential one-pot synthesis of pyrrolidine Lobelia alkaloids analogues.
Amara, Zacharias; Drège, Emmanuelle; Troufflard, Claire; Retailleau, Pascal; Joseph, Delphine; Organic & biomolecular chemistry 10 (2012) 7148–7157; doi:10.1039/c2ob25963j

data_7152575
_publ_section_title
;
 Solvent-free double aza-Michael under ultrasound irradiation:
 diastereoselective sequential one-pot synthesis of pyrrolidine Lobelia
 alkaloids analogues.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7148
_journal_page_last               7157
_journal_paper_doi               10.1039/c2ob25963j
_journal_volume                  10
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H28 N, Cl'
_chemical_formula_sum            'C21 H28 Cl N'
_chemical_formula_weight         329.89
_chemical_name_systematic
;
(meso)1-methyl-2,5-diphenethylpyrrolidin-1-ium chloride
;
_space_group_IT_number           41
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'A 2 -2ab'
_symmetry_space_group_name_H-M   'A b a 2'
_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            4
_cell_length_a                   25.438(2)
_cell_length_b                   10.6710(5)
_cell_length_c                   7.1250(2)
_cell_measurement_reflns_used    9798
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      71.6
_cell_measurement_theta_min      6.6
_cell_volume                     1934.07(19)
_computing_cell_refinement
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            12865
_diffrn_reflns_theta_full        73.14
_diffrn_reflns_theta_max         73.14
_diffrn_reflns_theta_min         6.96
_exptl_absorpt_coefficient_mu    1.721
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'regular parallelepiped'
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881; 855 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1891
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.307
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0544
_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^)+(0.1146P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1467
_refine_ls_wR_factor_ref         0.1763
_reflns_number_gt                1405
_reflns_number_total             1894
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25963j.txt
_cod_data_source_block           za231
_cod_original_sg_symbol_Hall     'A 2 -2ac'
_cod_database_code               7152575