Sulfonylation-Induced N- to O-Acetyl Migration in 2-Acetamidoethanol Derivatives
Takao Yamaguchi; Dusan Hesek; Mijoon Lee; Allen G. Oliver; Shahriar Mobashery; Journal of Organic Chemistry 75 (2010) 3515–3517; doi:10.1021/jo100456z

data_4025432
_publ_contact_author_address
;University of Notre Dame
Department of Chemistry and Biochemistry
251 Nieuwland Science Hall
Notre Dame, IN 46556-5670
USA
;
_publ_contact_author_email       mobashery@nd.edu
_publ_contact_author_fax         1(574)6316652
_publ_contact_author_name        'Professor Shahriar Mobashery'
_publ_contact_author_phone       1(574)6312933
_publ_section_title
;
 Sulfonylation-Induced N- to O-Acetyl Migration in 2-Acetamidoethanol
 Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3515
_journal_page_last               3517
_journal_paper_doi               10.1021/jo100456z
_journal_volume                  75
_journal_year                    2010
_chemical_compound_source        synthesized
_chemical_formula_moiety         'C15 H15 N O4 S'
_chemical_formula_sum            'C15 H15 N O4 S'
_chemical_formula_weight         305.34
_chemical_name_common            1-O-Tosyl-2-(acetamido)phenol
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                110.471(2)
_cell_angle_beta                 97.296(2)
_cell_angle_gamma                98.322(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5600(6)
_cell_length_b                   8.7553(6)
_cell_length_c                   10.5123(7)
_cell_measurement_reflns_used    7204
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      69.03
_cell_measurement_theta_min      4.57
_cell_volume                     716.79(9)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2007; Sheldrick, 2008)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.933
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0142
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8235
_diffrn_reflns_theta_full        69.53
_diffrn_reflns_theta_max         69.53
_diffrn_reflns_theta_min         4.57
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Simens DFFCU2K-90'
_exptl_absorpt_coefficient_mu    2.153
_exptl_absorpt_correction_T_max  0.7217
_exptl_absorpt_correction_T_min  0.5721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G. M. (2006). SADABS. University of G\"ottingen, Germany.'
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2512
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0485P)^2^+0.4454P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0889
_reflns_number_gt                2496
_reflns_number_total             2512
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100456z_si_001.cif
_cod_data_source_block           compound_2f
_cod_original_cell_volume        716.79(8)
_cod_original_sg_symbol_Hall     -P1
_cod_database_code               4025432