Sulfoxide-directed enantioselective synthesis of functionalized tetrahydropyridines.
Fernández de la Pradilla, Roberto; Simal, Carmen; Bates, Robert H.; Viso, Alma; Infantes, Lourdes; Organic letters 15 (2013) 4936–4939; doi:10.1021/ol402141d

data_1556228
_publ_section_title
;
 Sulfoxide-directed enantioselective synthesis of functionalized
 tetrahydropyridines.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4936
_journal_page_last               4939
_journal_paper_doi               10.1021/ol402141d
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration rmad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C24 H31 N O3 S2'
_chemical_formula_sum            'C24 H31 N O3 S2'
_chemical_formula_weight         445.62
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-02-15T11:04:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                79.648(4)
_cell_angle_beta                 84.413(4)
_cell_angle_gamma                82.507(4)
_cell_formula_units_Z            2
_cell_length_a                   8.2523(5)
_cell_length_b                   9.6600(6)
_cell_length_c                   15.0901(9)
_cell_measurement_reflns_used    8078
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      64.30
_cell_measurement_theta_min      2.99
_cell_volume                     1169.88(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Altomare, 1993)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.95
_diffrn_measured_fraction_theta_max 0.95
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \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  0.0558
_diffrn_reflns_av_unetI/netI     0.0798
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13617
_diffrn_reflns_theta_full        65.43
_diffrn_reflns_theta_max         65.43
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    2.257
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_correction_T_min  0.5245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction     
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.699
_refine_diff_density_min         -0.803
_refine_diff_density_rms         0.127
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.425
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         6427
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.424
_refine_ls_R_factor_all          0.1326
_refine_ls_R_factor_gt           0.121
_refine_ls_shift/su_max          0.01
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3148
_refine_ls_wR_factor_ref         0.3321
_reflns_number_gt                5514
_reflns_number_total             6427
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol402141d_si_004.cif
_cod_data_source_block           carmen5
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
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_cod_database_code               1556228