Dioxygenase-catalysed dihydroxylation of arene cis-dihydrodiols and acetonide derivatives: a new approach to the synthesis of enantiopure tetraoxygenated bioproducts from arenes
Boyd, Derek R.; Sharma, Narain D.; Belhocine, Tayeb; Malone, John F.; McGregor, Stuart; Allen, Christopher C. R.; Chemical Communications (Cambridge, United Kingdom)  (2006) 4934–4936; doi:10.1039/b612191h

data_7101589
_publ_section_title
;
 Dioxygenase-catalysed dihydroxylation of arene cis-dihydrodiols and acetonide
 derivatives: a new approach to the synthesis of enantiopure tetraoxygenated
 bioproducts from arenes
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   47
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              4934
_journal_page_last               4936
_journal_paper_doi               10.1039/b612191h
_journal_year                    2006
_chemical_formula_sum            'C35 H39 Cl3 O8'
_chemical_formula_weight         694.01
_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            8
_cell_length_a                   11.634(2)
_cell_length_b                   12.065(2)
_cell_length_c                   50.230(10)
_cell_measurement_reflns_used    985
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.62
_cell_measurement_theta_min      2.64
_cell_volume                     7050(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_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  0.0562
_diffrn_reflns_av_sigmaI/netI    0.0521
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       55
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_number            58452
_diffrn_reflns_theta_full        23.31
_diffrn_reflns_theta_max         23.31
_diffrn_reflns_theta_min         0.81
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8635
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             2912
_exptl_crystal_size_max          .60
_exptl_crystal_size_mid          .40
_exptl_crystal_size_min          .25
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(10)
_refine_ls_extinction_coef       0.0021(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   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     842
_refine_ls_number_reflns         10148
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0664
_refine_ls_shift/su_max          0.041
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1272P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1770
_refine_ls_wR_factor_ref         0.1982
_reflns_number_gt                6591
_reflns_number_total             10148
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b612191h.txt
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7101589