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_4022259
_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         'C11 H18 Cl3 N O3 '
_chemical_formula_sum            'C11 H18 Cl3 N O3'
_chemical_formula_weight         318.63
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_audit_creation_date             1998-08-12
_audit_creation_method           'by teXsan v1.7'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.347(2)
_cell_length_b                   17.944(2)
_cell_length_c                   11.441(2)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      37.8
_cell_measurement_theta_min      32.6
_cell_volume                     2945.4(5)
_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
;
SIR92 (Altomare, et. al. 1993)
;
_diffrn_ambient_temperature      296.2
_diffrn_measurement_device       'Rigaku AFC5R'
_diffrn_measurement_method       \w-2\q
_diffrn_orient_matrix_UB_11      -0.01911
_diffrn_orient_matrix_UB_12      0.05343
_diffrn_orient_matrix_UB_13      -0.00652
_diffrn_orient_matrix_UB_21      0.06043
_diffrn_orient_matrix_UB_22      0.01186
_diffrn_orient_matrix_UB_23      -0.03938
_diffrn_orient_matrix_UB_31      -0.02901
_diffrn_orient_matrix_UB_32      -0.01049
_diffrn_orient_matrix_UB_33      -0.07776
_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    0.100
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3070
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         79.01
_diffrn_reflns_theta_min         3.08
_diffrn_standards_decay_%        -4.92
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    5.776
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.669
_exptl_absorpt_correction_type
;
\y scans (North,Phillips & Matthews, 1968)
;
_exptl_crystal_colour            colourlessblock
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1328.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.50
_refine_diff_density_min         -0.47
_refine_ls_extinction_coef       0.00000066(9)
_refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.'
_refine_ls_extinction_method     'Zachariasen (1967)'
_refine_ls_goodness_of_fit_all   2.216
_refine_ls_goodness_of_fit_obs   2.739
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1613
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1425
_refine_ls_R_factor_obs          0.0745
_refine_ls_shift/esd_max         0.0000
_refine_ls_shift/esd_mean        0.0180
_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         0.0535
_refine_ls_wR_factor_obs         0.0501
_reflns_number_observed          1613
_reflns_number_total             3070
_reflns_observed_criterion       >2.00\s(I)
_cod_data_source_file            jo026161y_s6.cif
_cod_data_source_block           S668_SYN-42
_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) +
0.00002|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 

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'.

data
name '_geom_contact_site_symmetry_A' replaced with
'_geom_hbond_site_symmetry_A' 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 b c a    '
_cod_original_formula_sum        'C11 H18 Cl3 N O3 '
_cod_database_code               4022259