Rearrangement of 2,3-Epoxy Alcohol Dimethylthiocarbamate Derivatives. Synthesis of 2,3-Epithio Alcohol Derivatives under Mild Conditions
Przemysław Kalicki; Michał Karchier; Karol Michalak; Jerzy Wicha; Journal of Organic Chemistry 75 (2010) 5388–5391; doi:10.1021/jo101000u

data_4025575
_publ_section_title
;
 Rearrangement of 2,3-Epoxy Alcohol Dimethylthiocarbamate Derivatives.
 Synthesis of 2,3-Epithio Alcohol Derivatives under Mild Conditions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5388
_journal_page_last               5391
_journal_paper_doi               10.1021/jo101000u
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C26 H41 N O4 S'
_chemical_formula_sum            'C26 H41 N O4 S'
_chemical_formula_weight         463.66
_chemical_melting_point          478
_chemical_name_systematic
; 
S-[(20S)-17\a,20-Epoxy-3\b-(methoxymethoxy)pregn-5-en-16\b-yl]
 dimethylthiocarbamate
;
_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                   5.9928(2)
_cell_length_b                   12.2646(5)
_cell_length_c                   33.1829(14)
_cell_measurement_reflns_used    2908
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      67.58
_cell_measurement_theta_min      3.84
_cell_volume                     2438.92(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            9428
_diffrn_reflns_theta_full        65.08
_diffrn_reflns_theta_max         65.08
_diffrn_reflns_theta_min         3.84
_exptl_absorpt_coefficient_mu    1.431
_exptl_absorpt_correction_T_max  0.7930
_exptl_absorpt_correction_T_min  0.4811
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3863
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0564P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1079
_reflns_number_gt                3524
_reflns_number_total             3863
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101000u_si_002.cif
_cod_data_source_block           mka533_0m1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
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_cod_database_code               4025575