Photoinduced diastereoselective pinacolisation of 4-oxo-4-phenylbutanamides to 4,5-dihydroxy-4,5-diphenyloctanediamides
Lindemann, Ute; Neuburger, Markus; Neuburger-Zehnder, Margareta; Wulff-Molder, Dirk; Wessig, Pablo; Journal of the Chemical Society, Perkin Transactions 2  (1999) 2029–; doi:10.1039/a905040j

data_7213136
_publ_section_title
;
 Photoinduced diastereoselective pinacolisation of
 4-oxo-4-phenylbutanamides to 4,5-dihydroxy-4,5-diphenyloctanediamides
;
_journal_issue                   10
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              2029
_journal_paper_doi               10.1039/a905040j
_journal_year                    1999
_chemical_formula_structural     '[Ph--C(.5)-(CH2)2-COC]2'
_chemical_formula_sum            'C20 H18 O4'
_chemical_formula_weight         322.36
_chemical_melting_point          221(3)
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 95.910(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.4970(10)
_cell_length_b                   8.4210(10)
_cell_length_c                   10.0870(10)
_cell_measurement_reflns_used    32
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      19.7
_cell_measurement_theta_min      17.8
_cell_volume                     802.41(15)
_computing_cell_refinement       'STADI 4 (STOE, 1995)'
_computing_data_collection       'STADI 4 (STOE, 1995)'
_computing_data_reduction        'X-RED (STOE, 1995)'
_computing_publication_material  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Stoe STADI 4 diffractometer'
_diffrn_measurement_method       omega-2theta-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3130
_diffrn_reflns_theta_max         24.94
_diffrn_reflns_theta_min         2.16
_diffrn_standards_decay_%        15
_diffrn_standards_interval_time  4
_diffrn_standards_number         4
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   no
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       plates
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.760
_exptl_crystal_size_mid          0.475
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.100
_refine_diff_density_rms         0.025
_refine_ls_extinction_coef       0.0333(43)
_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   1.123
_refine_ls_goodness_of_fit_obs   1.153
_refine_ls_hydrogen_treatment    free
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1401
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_restrained_S_obs      1.153
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_obs          0.0324
_refine_ls_shift/esd_max         0.004
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0370P)^2^+0.1201P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0818
_refine_ls_wR_factor_obs         0.0792
_reflns_number_observed          1263
_reflns_number_total             1401
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            905040jsup1.cif
_cod_data_source_block           ute2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '218-224' was changed to '221(3)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0370P)^2^+0.1201P] 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^)+(0.0370P)^2^+0.1201P] 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 21/c '
_cod_database_code               7213136