Highly diastereoselective 1,3-dipolar cycloaddition reactions of trans-2-methylene-1,3-dithiolane 1,3-dioxide with 3-oxidopyridinium and 3-oxidopyrylium betaines: a route to the tropane skeleton
Aggarwal, Varinder K.; Grainger, Richard S.; Newton, Gary K.; Spargo, Peter L.; Hobson, Adrian D.; Adams, Harry; Organic & Biomolecular Chemistry 1 (2003) 1884–; doi:10.1039/b302834h

data_7151428
_publ_section_title
;
 Highly diastereoselective 1,3-dipolar cycloaddition reactions of
 trans-2-methylene-1,3-dithiolane 1,3-dioxide with 3-oxidopyridinium
 and 3-oxidopyrylium betaines: a route to the tropane skeleton
;
_journal_issue                   11
_journal_name_full               'Organic &amp;  Biomolecular Chemistry'
_journal_page_first              1884
_journal_paper_doi               10.1039/b302834h
_journal_volume                  1
_journal_year                    2003
_chemical_formula_sum            'C16 H17 N O3 S2'
_chemical_formula_weight         335.43
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 106.840(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.087(2)
_cell_length_b                   6.443(2)
_cell_length_c                   16.736(2)
_cell_measurement_reflns_used    37
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.629
_cell_measurement_theta_min      9.662
_cell_volume                     1557.1(6)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens XSCANS'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2748
_diffrn_reflns_theta_max         22.51
_diffrn_reflns_theta_min         2.53
_diffrn_standards_decay_%        19.83
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.353
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.075
_refine_ls_goodness_of_fit_obs   1.109
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_restrained_S_obs      1.109
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_obs          0.0418
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0559P)^2^+0.6583P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1117
_refine_ls_wR_factor_obs         0.1030
_reflns_number_observed          1660
_reflns_number_total             2031
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b302834h.txt
_cod_data_source_block           grange1
_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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0559P)^2^+0.6583P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0559P)^2^+0.6583P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7151428