Osmium-Catalyzed Vicinal Oxyamination of Alkenes by N-(4-Toluenesulfonyloxy)carbamates
Masruri; Anthony C. Willis; Malcolm D. McLeod; Journal of Organic Chemistry 77 (2012) 8480–8491; doi:10.1021/jo301372y

data_4027553
_publ_contact_author_address
;
Research School of Chemistry,
Australian National University,
Canberra, A. C. T. 0200, Australia
;
_publ_contact_author_email       'malcolm.mcleod@anu.edu.au '
_publ_contact_author_fax         ' 61 2 6125 8114 '
_publ_contact_author_name        'Malcolm D. McLeod'
_publ_contact_author_phone       ' 61 2 6125 3504 '
_publ_section_title
;
 Osmium-Catalyzed Vicinal Oxyamination of Alkenes by
 N-(4-Toluenesulfonyloxy)carbamates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8480
_journal_page_last               8491
_journal_paper_doi               10.1021/jo301372y
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration unk
_chemical_compound_source        local
_chemical_formula_moiety         'C12 H10 F5 N O4'
_chemical_formula_sum            'C12 H10 F5 N O4'
_chemical_formula_weight         327.21
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             10-11-10
_audit_creation_method           CRYSTALS_ver_12.87
_audit_update_record
;
2010-11-16 - Report on C12 H10 F5 N O4
             by Anthony C. Willis
             for  Masruri and Mal McLeod

2010-11-16 - passes checkcif tests with minor warnings  

;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3522(2)
_cell_length_b                   12.9233(3)
_cell_length_c                   9.3901(1)
_cell_measurement_reflns_used    16363
_cell_measurement_temperature    200
_cell_measurement_theta_max      30
_cell_measurement_theta_min      2.6
_cell_volume                     1377.60(4)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
; 
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       ' \f and \w scans with CCD '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            25020
_diffrn_reflns_theta_full        30.028
_diffrn_reflns_theta_max         30.028
_diffrn_reflns_theta_min         3.153
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.22
_refine_ls_abs_structure_details
;
The space group is polar but,
in the absence of significant anomalous scattering, 
the Friedel pairs have been merged
and the absolute structure has not been determined. 
The space group is not enantiomorphic so
the compound is present as a racemate within the crystal structure.
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.0015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2130
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0325
_refine_ls_shift/su_max          0.0061548
_refine_ls_shift/su_mean         0.0004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.15P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0829
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0829
_reflns_limit_h_max              15
_reflns_limit_h_min              0
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                1919
_reflns_number_total             2130
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.35
_oxford_diffrn_Wilson_scale      0.62
_oxford_refine_ls_r_factor_ref   0.0372
_oxford_refine_ls_scale          1.304(7)
_oxford_reflns_number_all        2130
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'transform axes for std setting of sp gp'
_cod_data_source_file            jo301372y_si_002.cif
_cod_data_source_block           mcl1007
_cod_original_sg_symbol_H-M      'P c a 21 '
_cod_database_code               4027553