Selective radical-chain epimerisation at electron-rich chiral tertiary C–H centres using thiols as protic polarity-reversal catalysts
Dang, Hai-Shan; Roberts, Brian P.; Tocher†, Derek A.; Journal of the Chemical Society, Perkin Transactions 1  (2001) 2452–; doi:10.1039/b103558b

data_7204970
_publ_section_title
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 Selective radical-chain epimerisation at electron-rich chiral tertiary
 C--H centres using thiols as protic polarity-reversal catalysts
;
_journal_issue                   19
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2452
_journal_paper_doi               10.1039/b103558b
_journal_year                    2001
_chemical_formula_sum            'C13 H22 O6'
_chemical_formula_weight         274.31
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.3710(10)
_cell_length_b                   10.704(2)
_cell_length_c                   25.652(5)
_cell_measurement_reflns_used    28
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      8.5
_cell_volume                     1474.8(5)
_computing_cell_refinement       P3
_computing_data_collection       P3
_computing_data_reduction        XDISK
_computing_molecular_graphics    XP
_computing_publication_material  CIFTAB
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Nicolet R3mV'
_diffrn_measurement_method       2theta
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1537
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         3.05
_diffrn_standards_decay_%        ~1.0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.097
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.76
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   4.17(246)
_refine_ls_extinction_coef       0.0635(75)
_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_all   1.045
_refine_ls_goodness_of_fit_obs   1.052
_refine_ls_hydrogen_treatment    'fixed positions and U(iso)'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1534
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_restrained_S_obs      1.052
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_obs          0.0483
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0871P)^2^+0.1577P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1468
_refine_ls_wR_factor_obs         0.1230
_reflns_number_observed          1154
_reflns_number_total             1537
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b103558b.txt
_cod_data_source_block           str681
_cod_depositor_comments
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The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0871P)^2^+0.1577P] 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^)+(0.0871P)^2^+0.1577P] 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      P2(1)2(1)2(1)
_cod_database_code               7204970