Stereoselectivity of the Thia-Sommelet [2,3]-Dearomatization
Richard Berger; Joseph W. Ziller; David L. Van Vranken; Journal of the American Chemical Society 120 (1998) 841–842; doi:10.1021/ja973734t

data_4116676
_publ_section_title
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 Stereoselectivity of the Thia-Sommelet [2,3]-Dearomatization
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_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              841
_journal_page_last               842
_journal_paper_doi               10.1021/ja973734t
_journal_volume                  120
_journal_year                    1998
_chemical_formula_sum            'C22 H25 N3 O2 S'
_chemical_formula_weight         395.51
_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           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 102.400(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.131(2)
_cell_length_b                   12.6429(9)
_cell_length_c                   9.044(3)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    296
_cell_measurement_theta_max      18.59
_cell_measurement_theta_min      7.00
_cell_volume                     2024.8(7)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        CARESS
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_structure_solution    'Siemens SHELXTL'
_diffrn_ambient_temperature      296
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6623
_diffrn_reflns_theta_max         60.00
_diffrn_reflns_theta_min         4.30
_diffrn_standards_decay_%        '< 1.0'
_diffrn_standards_interval_count 99
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    1.598
_exptl_absorpt_correction_T_max  0.9713
_exptl_absorpt_correction_T_min  0.6463
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       Plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_all   1.047
_refine_ls_goodness_of_fit_obs   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2409
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_restrained_S_obs      1.082
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_obs          0.0410
_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^)+(0.0579P)^2^+1.0353P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1160
_refine_ls_wR_factor_obs         0.1075
_reflns_number_observed          1984
_reflns_number_total             2409
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja973734t.cif
_cod_data_source_block           dvv4b
_cod_depositor_comments
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The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0579P)^2^+1.0353P] 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^)+(0.0579P)^2^+1.0353P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
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_cod_database_code               4116676