Improved microbiological hydroxylation of sesquiterpenoids: semisynthesis, structural determination and biotransformation studies of cyclic sulfite eudesmane derivatives
Andrés García-Granados; María C. Gutiérrez; Francisco Rivas; Org. Biomol. Chem. 1 (2003) 2314–2320; doi:10.1039/b301577g

data_7151412
_publ_section_title
;
 Improved microbiological hydroxylation of sesquiterpenoids:
 semisynthesis, structural determination and biotransformation studies
 of cyclic sulfite eudesmane derivatives
;
_journal_issue                   13
_journal_name_full               'Org. Biomol. Chem.'
_journal_page_first              2314
_journal_page_last               2320
_journal_paper_doi               10.1039/b301577g
_journal_volume                  1
_journal_year                    2003
_chemical_formula_sum            'C15 H24 O4 S'
_chemical_formula_weight         300.4
_chemical_name_common            '1-OXO-4B,6B-DIYL-S(S)-CYCLIC SULPHITE'
_chemical_name_systematic
;
1-OXO-4B,6B-DIYL-S(S)-CYCLIC SULPHITE
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.519(1)
_cell_length_b                   9.782(1)
_cell_length_c                   18.631(2)
_cell_measurement_reflns_used    38
_cell_measurement_temperature    294(1)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      10
_cell_volume                     1552.6(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      294
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            3332
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.825
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'short prism'
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.20(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0613P)^2^+0.0749P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1086
_reflns_number_gt                2609
_reflns_number_total             3129
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b301577g.txt
_cod_data_source_block           1-oxo-4b,6b-diyl-S(S)-cyclic_sulphite
_cod_original_cell_volume        1552.6(2)
_cod_original_sg_symbol_H-M      'P 212121'
_cod_database_code               7151412