#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/54/4025432.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4025432
loop_
_publ_author_name
'Takao Yamaguchi'
'Dusan Hesek'
'Mijoon Lee'
'Allen G. Oliver'
'Shahriar Mobashery'
_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       'φ and ω 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 Göttingen, 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/[σ²(Fo²)+(0.0485P)²+0.4454P] where P=(Fo²+2Fc²)/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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.68817(15) 0.70651(16) 0.09437(13) 0.0178(3) Uani 1 1 d . . .
H1N H 0.6546 0.7593 0.0421 0.021 Uiso 1 1 calc R . .
S1 S 0.41654(4) 1.00926(4) 0.19510(4) 0.01751(13) Uani 1 1 d . . .
O1 O 0.40717(12) 0.81836(13) 0.09712(10) 0.0176(2) Uani 1 1 d . . .
O2 O 0.90681(15) 0.6173(2) 0.16848(15) 0.0422(4) Uani 1 1 d . . .
O3 O 0.31980(13) 1.01228(14) 0.29667(12) 0.0238(3) Uani 1 1 d . . .
O4 O 0.37751(13) 1.08441(14) 0.09783(12) 0.0230(3) Uani 1 1 d . . .
C1 C 0.42957(18) 0.70467(19) 0.16306(15) 0.0169(3) Uani 1 1 d . . .
C2 C 0.57443(18) 0.64825(19) 0.16117(14) 0.0169(3) Uani 1 1 d . . .
C3 C 0.59574(19) 0.53563(19) 0.22545(16) 0.0199(3) Uani 1 1 d . . .
H3 H 0.6916 0.4928 0.2251 0.024 Uiso 1 1 calc R . .
C4 C 0.4771(2) 0.4860(2) 0.28988(16) 0.0229(3) Uani 1 1 d . . .
H4 H 0.4948 0.4127 0.3364 0.028 Uiso 1 1 calc R . .
C5 C 0.3334(2) 0.5413(2) 0.28753(17) 0.0243(4) Uani 1 1 d . . .
H5 H 0.2528 0.5046 0.3307 0.029 Uiso 1 1 calc R . .
C6 C 0.30800(19) 0.6506(2) 0.22174(16) 0.0210(3) Uani 1 1 d . . .
H6 H 0.2091 0.6875 0.2171 0.025 Uiso 1 1 calc R . .
C7 C 0.84527(19) 0.6900(2) 0.10184(16) 0.0238(4) Uani 1 1 d . . .
C8 C 0.9401(2) 0.7721(2) 0.02349(19) 0.0297(4) Uani 1 1 d . . .
H8A H 1.0090 0.8770 0.0884 0.045 Uiso 1 1 calc R . .
H8B H 0.8659 0.7946 -0.0437 0.045 Uiso 1 1 calc R . .
H8C H 1.0070 0.6981 -0.0252 0.045 Uiso 1 1 calc R . .
C9 C 0.61888(18) 1.08351(19) 0.27757(15) 0.0174(3) Uani 1 1 d . . .
C10 C 0.72209(19) 1.17023(19) 0.22245(15) 0.0199(3) Uani 1 1 d . . .
H10 H 0.6846 1.1855 0.1396 0.024 Uiso 1 1 calc R . .
C11 C 0.88033(19) 1.2338(2) 0.29071(16) 0.0215(3) Uani 1 1 d . . .
H11 H 0.9514 1.2948 0.2548 0.026 Uiso 1 1 calc R . .
C12 C 0.93761(19) 1.2098(2) 0.41157(15) 0.0196(3) Uani 1 1 d . . .
C13 C 0.83207(19) 1.1196(2) 0.46281(16) 0.0213(3) Uani 1 1 d . . .
H13 H 0.8702 1.1011 0.5440 0.026 Uiso 1 1 calc R . .
C14 C 0.67235(19) 1.0564(2) 0.39719(16) 0.0206(3) Uani 1 1 d . . .
H14 H 0.6009 0.9959 0.4331 0.025 Uiso 1 1 calc R . .
C15 C 1.1090(2) 1.2833(2) 0.48596(17) 0.0251(4) Uani 1 1 d . . .
H15A H 1.1296 1.2510 0.5659 0.038 Uiso 1 1 calc R . .
H15B H 1.1275 1.4049 0.5174 0.038 Uiso 1 1 calc R . .
H15C H 1.1818 1.2418 0.4230 0.038 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C2 127.09(13) . . ?
C7 N1 H1N 116.5 . . ?
C2 N1 H1N 116.5 . . ?
O3 S1 O4 119.91(7) . . ?
O3 S1 O1 108.80(6) . . ?
O4 S1 O1 102.75(6) . . ?
O3 S1 C9 109.00(7) . . ?
O4 S1 C9 110.50(7) . . ?
O1 S1 C9 104.68(6) . . ?
C1 O1 S1 117.28(9) . . ?
C6 C1 C2 123.02(14) . . ?
C6 C1 O1 119.59(13) . . ?
C2 C1 O1 117.36(13) . . ?
C3 C2 C1 117.22(14) . . ?
C3 C2 N1 124.19(14) . . ?
C1 C2 N1 118.58(14) . . ?
C4 C3 C2 120.18(14) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 121.25(15) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 119.62(15) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 118.61(14) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
O2 C7 N1 123.38(15) . . ?
O2 C7 C8 121.62(15) . . ?
N1 C7 C8 114.98(14) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 121.52(14) . . ?
C10 C9 S1 118.93(12) . . ?
C14 C9 S1 119.55(12) . . ?
C11 C10 C9 118.70(14) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C12 121.21(15) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 118.75(14) . . ?
C13 C12 C15 120.88(14) . . ?
C11 C12 C15 120.36(15) . . ?
C14 C13 C12 121.11(14) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C9 118.68(15) . . ?
C13 C14 H14 120.7 . . ?
C9 C14 H14 120.7 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.369(2) . ?
N1 C2 1.4077(19) . ?
N1 H1N 0.8800 . ?
S1 O3 1.4275(12) . ?
S1 O4 1.4275(11) . ?
S1 O1 1.6115(11) . ?
S1 C9 1.7529(15) . ?
O1 C1 1.4185(18) . ?
O2 C7 1.220(2) . ?
C1 C6 1.383(2) . ?
C1 C2 1.400(2) . ?
C2 C3 1.396(2) . ?
C3 C4 1.390(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.506(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.391(2) . ?
C9 C14 1.393(2) . ?
C10 C11 1.384(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.399(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.395(2) . ?
C12 C15 1.504(2) . ?
C13 C14 1.388(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 497796
