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_4022257
_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_sum            'C13 H16 Cl3 N O7'
_chemical_formula_weight         404.62
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             1999-10-18
_audit_creation_method           'by teXsan v1.7'
_cell_angle_alpha                115.014(11)
_cell_angle_beta                 115.946(12)
_cell_angle_gamma                74.141(13)
_cell_formula_units_Z            2
_cell_length_a                   10.2633(18)
_cell_length_b                   10.9378(13)
_cell_length_c                   9.7783(18)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      39.9
_cell_measurement_theta_min      39.6
_cell_volume                     889.2(2)
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
SHELXS86 (Sheldrick, 1985)
;
_diffrn_ambient_temperature      296.2
_diffrn_measured_fraction_theta_full 0.930
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device       'Rigaku AFC5R'
_diffrn_measurement_method       \w-2\q
_diffrn_orient_matrix_UB_11      -0.05504
_diffrn_orient_matrix_UB_12      0.04912
_diffrn_orient_matrix_UB_13      0.07438
_diffrn_orient_matrix_UB_21      -0.00987
_diffrn_orient_matrix_UB_22      0.08519
_diffrn_orient_matrix_UB_23      -0.01982
_diffrn_orient_matrix_UB_31      -0.09356
_diffrn_orient_matrix_UB_32      -0.02508
_diffrn_orient_matrix_UB_33      -0.09393
_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  0.0391
_diffrn_reflns_av_sigmaI/netI    0.0213
_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       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3748
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        77.93
_diffrn_reflns_theta_max         77.93
_diffrn_reflns_theta_min         4.49
_diffrn_standards_decay_%        20.50
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.993
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.474
_exptl_absorpt_correction_type
;
\y scans (North,Phillips & Matthews, 1968)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.690
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.037(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   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3538
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0574
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0918P)^2^+0.6623P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1589
_refine_ls_wR_factor_ref         0.1672
_reflns_number_gt                3179
_reflns_number_total             3538
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo026161y_s4.cif
_cod_data_source_block           s770_ANTI-32
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0918P)^2^+0.6623P] where P=(Fo^2^+2Fc^2^)/3' 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^2^)+(0.0918P)^2^+0.6623P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P -1       '
_cod_database_code               4022257