A Short Diastereoselective Synthesis of the Putative Alkaloid Jamtine, Using a Tandem Pummerer/Mannich Cyclization Sequence
Albert Padwa; M. Diana Danca; Kenneth I. Hardcastle; Michael S. McClure; Journal of Organic Chemistry 68 (2003) 929–941; doi:10.1021/jo026471g

data_4022306
_publ_contact_author_address
;
Emory University
Department of Chemistry
X-ray Crystallography Center
Atlanta GA  30322
USA
;
_publ_contact_author_email       khardca@emory.edu
_publ_contact_author_fax         404-727-6586
_publ_contact_author_name        'Kenneth I. Hardcastle'
_publ_contact_author_phone       404-727-6140
_publ_section_title
;
 A Short Diastereoselective Synthesis of the Putative Alkaloid Jamtine,
 Using a Tandem Pummerer/Mannich Cyclization Sequence
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              929
_journal_page_last               941
_journal_paper_doi               10.1021/jo026471g
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C21 H27 N O4 S'
_chemical_formula_weight         389.50
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.1120(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4474(2)
_cell_length_b                   9.0088(2)
_cell_length_c                   22.8671(4)
_cell_measurement_reflns_used    6344
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.965
_cell_measurement_theta_min      3.876
_cell_volume                     1941.20(7)
_computing_cell_refinement       'Bruker SMART/SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8659
_diffrn_reflns_theta_full        65.96
_diffrn_reflns_theta_max         65.96
_diffrn_reflns_theta_min         3.88
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    1.703
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.694504
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS in SHELXTL 5.1, Sheldrick 1997'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'hex block'
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         3253
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0782P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1038
_reflns_number_gt                2814
_reflns_number_total             3253
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo026471gsi20021107_031521.cif
_cod_data_source_block           ddlts
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4022306