Conformational Analysis of Sulfur-Containing 6-Deoxy-L-hexose Derivatives by Molecular Modeling and NMR Spectroscopy. A Theoretical Study and Experimental Evidence of Intramolecular Nonbonded Interactions between Sulfur and Oxygen
Mabel Fragoso-Serrano; Georgina Guillén-Jaramillo; Rogelio Pereda-Miranda; Carlos M. Cerda-García-Rojas; Journal of Organic Chemistry 68 (2003) 7167–7175; doi:10.1021/jo034492k

data_4022477
_publ_contact_author
;
  Dr. Carlos M. Cerda-Garcia-Rojas
  Departamento de Quimica
  CINVESTAV-IPN
  Av. Instituto Politecnico Nacional 2508
  07360 Mexico City
  Mexico

;
_publ_contact_author_email       ccerda@mail.cinvestav.mx
_publ_contact_author_fax         '5255 57477137'
_publ_contact_author_phone       '5255 50613800 ext 4035'
_publ_section_title
;
 Conformational Analysis of Sulfur-Containing 6-Deoxy-L-hexose
 Derivatives by Molecular Modeling and NMR Spectroscopy.
 A Theoretical Study and Experimental Evidence of Intramolecular
 Nonbonded Interactions between Sulfur and Oxygen
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7167
_journal_page_last               7175
_journal_paper_doi               10.1021/jo034492k
_journal_volume                  68
_journal_year                    2003
_chemical_formula_moiety         'C12 H18 O5 S2'
_chemical_formula_sum            'C12 H18 O5 S2'
_chemical_formula_weight         306.38
_chemical_melting_point          111.0(10)
_chemical_name_systematic
;
(4aR,6S,7S,8R,8aS)-7,8-diacetyloxy-6-methylhexahydro-4aH-[1,4]dithiino
[2,3b]pyran.
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1347(3)
_cell_length_b                   9.4741(3)
_cell_length_c                   18.1026(6)
_cell_measurement_reflns_used    100
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      7
_cell_volume                     1566.65(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'XPMA (Zsolnai, 1997)'
_computing_publication_material  'CIFTAB (Sheldrick, 1992-7)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10469
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.25
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    0.351
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(8)
_refine_ls_extinction_coef       0.076(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2659
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0694P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1004
_reflns_number_gt                2659
_reflns_number_total             3086
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo034492ksi20030626_090712.cif
_cod_data_source_block           pyran
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '110-112' was changed to '111.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4022477