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_7151413
_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(R)-CYCLIC SULPHITE'
_chemical_name_systematic
;
1-OXO-4B,6B-DIYL-S(R)-CYCLIC SULPHITE
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 106.32(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.321(2)
_cell_length_b                   7.996(2)
_cell_length_c                   11.132(2)
_cell_measurement_reflns_used    29
_cell_measurement_temperature    294(1)
_cell_measurement_theta_max      18.2
_cell_measurement_theta_min      15
_cell_volume                     796.2(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      294(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3060
_diffrn_reflns_theta_full        32.53
_diffrn_reflns_theta_max         32.53
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'short prism'
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.18(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3060
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.166
_refine_ls_R_factor_all          0.1050
_refine_ls_R_factor_gt           0.0672
_refine_ls_shift/su_max          0.053
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0626P)^2^+0.1946P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1455
_refine_ls_wR_factor_ref         0.1730
_reflns_number_gt                2084
_reflns_number_total             3060
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b301577g.txt
_cod_data_source_block           1-oxo-4b,6b-diyl-S(R)-cyclic_sulphite
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7151413