Investigation of Diastereoselective Acyclic α-Alkoxydithioacetal Substitutions Involving Thiacarbenium Intermediates.
Prévost, Michel; Dostie, Starr; Waltz, Marie-Ève; Guindon, Yvan; The Journal of organic chemistry 79 (2014) 10504–; doi:10.1021/jo502181a

data_4030081
_publ_section_title
;
 Investigation of Diastereoselective Acyclic \a-Alkoxydithioacetal
 Substitutions Involving Thiacarbenium Intermediates.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10504
_journal_paper_doi               10.1021/jo502181a
_journal_volume                  79
_journal_year                    2014
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C12 H16 N2 O5'
_chemical_formula_sum            'C12 H16 N2 O5'
_chemical_formula_weight         268.27
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 101.4011(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5811(2)
_cell_length_b                   21.9839(6)
_cell_length_c                   10.4340(3)
_cell_measurement_reflns_used    2638
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      55.84
_cell_measurement_theta_min      4.02
_cell_volume                     1254.93(7)
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.870
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measurement_device_type  'Bruker Smart 6000'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13217
_diffrn_reflns_theta_full        68.67
_diffrn_reflns_theta_max         68.67
_diffrn_reflns_theta_min         4.02
_diffrn_standards_decay_%        0.00
_diffrn_standards_number         62
_exptl_absorpt_coefficient_mu    0.942
_exptl_absorpt_correction_T_max  0.9900
_exptl_absorpt_correction_T_min  0.7500
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick,1996)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2027
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0437P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0905
_reflns_number_gt                1344
_reflns_number_total             2027
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo502181a_si_003.cif
_cod_data_source_block           guin34
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_geom_bond_publ_flag' value 'Y' changed to 'y'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26 (21
time).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26 (33
times).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according
to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26 (43
times).

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 4030080--4030081.cif.
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_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4030081