Dioxygenase-catalysed mono-, di- and tri-oxygenation of dialkyl sulfides and thioacetals: chemoenzymatic synthesis of enantiopure cis-diol sulfoxides
Derek R. Boyd; Narain D. Sharma; Simon A. Haughey; John F. Malone; Alistair W. T. King; Brian T. McMurray; André Alves-Areias; Christopher C. R. Allen; Robert Holt; Howard Dalton; Journal of the Chemical Society, Perkin Transactions 1  (2001) 3288–3296; doi:10.1039/b108620k

data_7213521
_publ_section_title
;
 Dioxygenase-catalysed mono-, di- and tri-oxygenation of dialkyl sulfides
 and thioacetals: chemoenzymatic synthesis of enantiopure cis-diol
 sulfoxides
;
_journal_issue                   24
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              3288
_journal_page_last               3296
_journal_paper_doi               10.1039/b108620k
_journal_year                    2001
_chemical_formula_sum            'C8 H12 O3 S'
_chemical_formula_weight         188.24
_chemical_melting_point          123
_chemical_name_systematic
;
cis-(1S,2R)-3-(R-methylsulfinylmethyl)cyclohexa-3,5-diene-1,2-diol 
;
_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   difmap
_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                   5.3260(10)
_cell_length_b                   8.8440(10)
_cell_length_c                   18.602(3)
_cell_measurement_reflns_used    29
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      10.2
_cell_volume                     876.2(2)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker XSCANS'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            938
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.333
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.26(19)
_refine_ls_extinction_coef       0.002(2)
_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   1.114
_refine_ls_hydrogen_treatment    refined
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         938
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0556P)^2^+0.1884P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0933
_reflns_number_gt                843
_reflns_number_total             938
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b108620ksup1.cif
_cod_data_source_block           27
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7213521