Enantioselective, protecting group-free synthesis of 1S-ethyl-4-substituted quinolizidines.
Amat, Mercedes; Semak, Vladislav; Escolano, Carmen; Molins, Elies; Bosch, Joan; Organic & biomolecular chemistry 10 (2012) 6866–6875; doi:10.1039/c2ob25392e

data_7152546
_publ_section_title
;
 Enantioselective, protecting group-free synthesis of
 1S-ethyl-4-substituted quinolizidines.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6866
_journal_page_last               6875
_journal_paper_doi               10.1039/c2ob25392e
_journal_volume                  10
_journal_year                    2012
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H25 N1 O2'
_chemical_formula_sum            'C18 H25 N O2'
_chemical_formula_weight         287.39
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2011-02-15T12:25:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 104.96(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.938(3)
_cell_length_b                   23.823(4)
_cell_length_c                   9.277(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      12.1
_cell_measurement_theta_min      8
_cell_measurement_wavelength     0.71073
_cell_volume                     1694.9(9)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled \w scans'
_diffrn_orient_matrix_type
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      0.069463
_diffrn_orient_matrix_UB_12      0.025334
_diffrn_orient_matrix_UB_13      0.079312
_diffrn_orient_matrix_UB_21      0.001098
_diffrn_orient_matrix_UB_22      -0.029584
_diffrn_orient_matrix_UB_23      0.076725
_diffrn_orient_matrix_UB_31      0.110276
_diffrn_orient_matrix_UB_32      -0.015646
_diffrn_orient_matrix_UB_33      -0.016653
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0906
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3691
_diffrn_reflns_theta_full        26.97
_diffrn_reflns_theta_max         26.97
_diffrn_reflns_theta_min         1.71
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.7774
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.888
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3691
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      0.888
_refine_ls_R_factor_all          0.1709
_refine_ls_R_factor_gt           0.0528
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0607P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1479
_reflns_number_gt                1335
_reflns_number_total             3691
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25392e.txt
_cod_data_source_block           jb87
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               7152546