Inverted regioselectivity of C-H amination: Unexpected oxidation at beta- rather than gamma-C-H.
Wyszynski, Filip J.; Thompson, Amber L.; Davis, Benjamin G.; Organic & biomolecular chemistry 8 (2010) 4246–4248; doi:10.1039/c0ob00113a

data_7153431
_publ_section_title
;
 Inverted regioselectivity of C-H amination: Unexpected oxidation at beta-
 rather than gamma-C-H.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4246
_journal_page_last               4248
_journal_paper_doi               10.1039/c0ob00113a
_journal_volume                  8
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C9 H15 N1 O7 S1'
_chemical_formula_sum            'C9 H15 N O7 S'
_chemical_formula_weight         281.29
_chemical_melting_point          ?
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             08-07-24
_audit_creation_method           CRYSTALS_ver_12.86
_cell_angle_alpha                80.5318(12)
_cell_angle_beta                 84.2434(12)
_cell_angle_gamma                89.0269(12)
_cell_formula_units_Z            1
_cell_length_a                   6.0756(2)
_cell_length_b                   6.6423(2)
_cell_length_c                   7.3505(2)
_cell_measurement_reflns_used    1305
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     291.120(15)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_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      150
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6964
_diffrn_reflns_theta_full        26.944
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         5.483
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             148
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.24
_refine_ls_abs_structure_details 'Flack (1983), 1221 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2545
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0232
_refine_ls_shift/su_max          0.000162
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 0.06P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0570
_refine_ls_wR_factor_gt          0.0567
_refine_ls_wR_factor_ref         0.0570
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              9
_reflns_limit_l_min              -9
_reflns_number_gt                2498
_reflns_number_total             2545
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.59
_oxford_diffrn_Wilson_scale      0.14
_oxford_refine_ls_r_factor_ref   0.0238
_oxford_refine_ls_scale          2.597(18)
_oxford_reflns_number_all        2545
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 5940
_cod_data_source_file            c0ob00113a.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_symmetry_cell_setting' value
'Triclinic' changed to 'triclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

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

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 1 '
_cod_original_formula_sum        'C9 H15 N1 O7 S1'
_cod_database_code               7153431