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_4022261
_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            'C19 H36 Cl5 N3 O5 Os'
_chemical_formula_weight         753.98
_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'
_audit_creation_date             1998-06-16
_audit_creation_method           'by teXsan v1.7'
_cell_angle_alpha                101.31(4)
_cell_angle_beta                 119.63(3)
_cell_angle_gamma                73.15(3)
_cell_formula_units_Z            2
_cell_length_a                   11.595(6)
_cell_length_b                   12.862(5)
_cell_length_c                   11.561(6)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      0.0
_cell_measurement_theta_min      0.0
_cell_volume                     1431(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)'
_diffrn_ambient_temperature      296.2
_diffrn_measurement_device       'Rigaku AFC6S'
_diffrn_orient_matrix_UB_11      -0.03506
_diffrn_orient_matrix_UB_12      -0.00776
_diffrn_orient_matrix_UB_13      0.06066
_diffrn_orient_matrix_UB_21      -0.03520
_diffrn_orient_matrix_UB_22      0.08066
_diffrn_orient_matrix_UB_23      0.00460
_diffrn_orient_matrix_UB_31      -0.08892
_diffrn_orient_matrix_UB_32      -0.00777
_diffrn_orient_matrix_UB_33      -0.07900
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.02308
_diffrn_reflns_av_sigmaI/netI    0.060
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5326
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.66
_diffrn_standards_decay_%        -0.43
_diffrn_standards_interval_count 0
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.950
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_type
;
\y scans (North,Phillips & Matthews, 1968)
;
_exptl_crystal_colour            unknown
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_density_meas      ?
_exptl_crystal_description       unknown
_exptl_crystal_F_000             744.00
_exptl_crystal_size_max          0.00
_exptl_crystal_size_mid          0.00
_exptl_crystal_size_min          0.00
_refine_diff_density_max         0.82
_refine_diff_density_min         -0.79
_refine_ls_extinction_coef       0.00000041(3)
_refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.'
_refine_ls_extinction_method     'Zachariasen (1967)'
_refine_ls_goodness_of_fit_all   1.609
_refine_ls_goodness_of_fit_obs   1.521
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_obs          0.0354
_refine_ls_shift/esd_max         0.0000
_refine_ls_shift/esd_mean        0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo) + 0.00003|Fo|^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0369
_refine_ls_wR_factor_obs         0.0316
_reflns_number_observed          4202
_reflns_number_total             5053
_reflns_observed_criterion       >2.00\s(I)
_cod_data_source_file            jo026161y_s8.cif
_cod_data_source_block           S667_CMPD-51
_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

 Adding the '_geom_hbond_atom_site_label_A' data item. Values of the
 data item were determined from the geometry of the molecule.

 Antanas Vaitkus,
 2017-03-06

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(Fo) +
0.00003|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) + 0.00003|Fo|^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 

The following automatic conversions were performed:
data name '_geom_bond_atom_site_label_D' replaced with
'_geom_hbond_atom_site_label_D' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_bond_atom_site_label_H' replaced with
'_geom_hbond_atom_site_label_H' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_bond_distance_DH' replaced with '_geom_hbond_distance_DH'
as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_contact_distance_HA' replaced with
'_geom_hbond_distance_HA' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_contact_distance_DA' replaced with
'_geom_hbond_distance_DA' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_angle_DHA' replaced with '_geom_hbond_angle_DHA' as
specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 5005 2017-03-03 11:38:54Z antanas 
;
_cod_original_sg_symbol_H-M      'P -1       '
_cod_original_formula_sum        'C19 H36 Cl5 N3 O5 Os '
_cod_database_code               4022261