Directed Dihydroxylation of Cyclic Allylic Alcohols and Trichloroacetamides Using OsO~4~/TMEDA
Timothy J. Donohoe; Kevin Blades; Peter R. Moore; Michael J. Waring; Jon J. G. Winter; Madeleine Helliwell; Nicholas J. Newcombe; Geoffrey Stemp; Journal of Organic Chemistry 67 (2002) 7946–7956; doi:10.1021/jo026161y

data_4022258
_publ_section_title
;
 Directed Dihydroxylation of Cyclic Allylic Alcohols and
 Trichloroacetamides Using OsO~4~/TMEDA
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7946
_journal_page_last               7956
_journal_paper_doi               10.1021/jo026161y
_journal_volume                  67
_journal_year                    2002
_chemical_formula_moiety         'C20 H24 O11 S '
_chemical_formula_sum            'C20 H24 O11 S'
_chemical_formula_weight         472.46
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_date             19102-04-04
_audit_creation_method           'by teXsan v1.7'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.947(6)
_cell_length_b                   20.304(4)
_cell_length_c                   8.817(4)
_cell_measurement_reflns_used    19
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      37.5
_cell_measurement_theta_min      31.3
_cell_volume                     2317(1)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan (MSC, 1995)'
_computing_publication_material  'teXsan (MSC, 1995)'
_computing_structure_refinement  'teXsan (MSC, 1995)'
_computing_structure_solution
;
SHELXS86 (Sheldrick, 1985)
;
_diffrn_ambient_temperature      296.2
_diffrn_measurement_device       'Rigaku AFC5R'
_diffrn_measurement_method       \w-2\q
_diffrn_orient_matrix_UB_11      -0.02354
_diffrn_orient_matrix_UB_12      -0.04687
_diffrn_orient_matrix_UB_13      -0.00423
_diffrn_orient_matrix_UB_21      -0.07344
_diffrn_orient_matrix_UB_22      0.01486
_diffrn_orient_matrix_UB_23      0.00806
_diffrn_orient_matrix_UB_31      -0.00436
_diffrn_orient_matrix_UB_32      0.00282
_diffrn_orient_matrix_UB_33      -0.11305
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.00000
_diffrn_reflns_av_sigmaI/netI    0.070
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2580
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         77.14
_diffrn_reflns_theta_min         3.41
_diffrn_standards_decay_%        4.28
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.750
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.832
_exptl_absorpt_correction_type
;
\y scans (North,Phillips & Matthews, 1968)
;
_exptl_crystal_colour            colourlessprismatic
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             992.00
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.25
_refine_ls_extinction_coef       0.0000035(2)
_refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.'
_refine_ls_extinction_method     'Zachariasen (1967)'
_refine_ls_goodness_of_fit_all   1.826
_refine_ls_goodness_of_fit_obs   1.971
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     290
_refine_ls_number_reflns         2026
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_obs          0.0489
_refine_ls_shift/esd_max         0.0000
_refine_ls_shift/esd_mean        0.0500
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo) + 0.00002|Fo|^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0409
_refine_ls_wR_factor_obs         0.0387
_reflns_number_observed          2026
_reflns_number_total             2580
_reflns_observed_criterion       >2.00\s(I)
_cod_data_source_file            jo026161y_s5.cif
_cod_data_source_block           S736_SYN-22
_cod_depositor_comments
;
 Renaming the _geom_torsion_site_symmetry_4 data item to _geom_torsion.
 The initial data name misassignment was cause by the incorrect data name
 order in the loop and the removal of data items containing only unknown
 ('?') or inapplicable ('.') values.

 Antanas Vaitkus,
 2018-08-08

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(Fo) +
0.00002|Fo|^2^]' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 1/[\s^2^(Fo) + 0.00002|Fo|^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C20 H24 O11 S '
_cod_database_code               4022258