# Supplementary Material (ESI) for Organic and Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2009

data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Bhisma Patel'
_publ_contact_author_email       PATEL@IITG.ERNET.IN

_publ_section_title              
;
Hypervalent iodine (III) mediated oxidation
of aldoximes to N-acetoxy or N-hydroxy amides
;
loop_
_publ_author_name
'Bhisma Patel'
'Harisadhan Ghosh'

# Attachment '_9a_cif.cif'

data_hg-1
_database_code_depnum_ccdc_archive 'CCDC 744680'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'N-Acetoxy-2,6-dichloro-benzamide '
_chemical_name_common            N-Acetoxy-2,6-dichloro-benzamide
_chemical_formula_moiety         'C9 H7 Cl2 N O3'
_chemical_formula_sum            'C9 H7 Cl2 N O3'
_exptl_crystal_recrystallization_method CHCl3
_chemical_melting_point          164

_exptl_crystal_description       blocks
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         248.06

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic

_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.8316(4)

_cell_length_b                   12.1236(5)

_cell_length_c                   8.8033(3)

_cell_angle_alpha                90.00

_cell_angle_beta                 92.170(2)

_cell_angle_gamma                90.00

_cell_volume                     1048.55(7)

_cell_formula_units_Z            4

_cell_measurement_temperature    298(2)

_cell_measurement_reflns_used    3653

_cell_measurement_theta_min      2.67

_cell_measurement_theta_max      26.94
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;
_diffrn_radiation_probe          ?

_diffrn_radiation_type           MoK\a

_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7954
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         24.49
_reflns_number_total             1655
_reflns_number_gt                1415
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0439P)^2^+0.1367P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1655
_refine_ls_number_parameters     141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0779
_refine_ls_wR_factor_gt          0.0753
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

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
Cl1 Cl 0.89489(5) 1.02832(4) 0.16257(5) 0.05339(19) Uani 1 1 d . . .
Cl2 Cl 0.52876(6) 0.72173(5) -0.01864(6) 0.0596(2) Uani 1 1 d . . .
C6 C 0.56821(18) 0.84285(15) 0.07932(17) 0.0387(4) Uani 1 1 d . . .
C1 C 0.70140(17) 0.87983(14) 0.08211(16) 0.0336(4) Uani 1 1 d . . .
C2 C 0.73012(18) 0.97766(15) 0.15928(18) 0.0376(4) Uani 1 1 d . . .
C3 C 0.6298(2) 1.03633(16) 0.22950(19) 0.0446(5) Uani 1 1 d . . .
H3 H 0.6508 1.1016 0.2807 0.054 Uiso 1 1 calc R . .
C4 C 0.4983(2) 0.99687(17) 0.2226(2) 0.0485(5) Uani 1 1 d . . .
H4 H 0.4304 1.0364 0.2691 0.058 Uiso 1 1 calc R . .
C5 C 0.46562(19) 0.90000(17) 0.14826(18) 0.0452(5) Uani 1 1 d . . .
H5 H 0.3767 0.8736 0.1445 0.054 Uiso 1 1 calc R . .
C7 C 0.80515(17) 0.82085(15) -0.00976(17) 0.0356(4) Uani 1 1 d . . .
O1 O 0.81947(13) 0.84273(11) -0.14389(12) 0.0471(3) Uani 1 1 d . . .
N1 N 0.87397(17) 0.74402(14) 0.06734(18) 0.0470(4) Uani 1 1 d . . .
O2 O 0.95342(13) 0.67098(11) -0.01510(13) 0.0460(3) Uani 1 1 d . . .
C8 C 1.0918(2) 0.68732(16) 0.00655(19) 0.0418(5) Uani 1 1 d . . .
O3 O 1.13842(17) 0.75547(13) 0.08853(19) 0.0685(4) Uani 1 1 d . . .
C9 C 1.1641(2) 0.60544(18) -0.0865(2) 0.0546(5) Uani 1 1 d . . .
H9A H 1.2597 0.6217 -0.0830 0.082 Uiso 1 1 calc R . .
H9B H 1.1294 0.6089 -0.1898 0.082 Uiso 1 1 calc R . .
H9C H 1.1499 0.5328 -0.0467 0.082 Uiso 1 1 calc R . .
H1N H 0.858(2) 0.7246(16) 0.153(2) 0.051(6) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0432(4) 0.0586(4) 0.0585(3) -0.0109(2) 0.0034(2) -0.0100(2)
Cl2 0.0571(4) 0.0604(4) 0.0617(3) -0.0130(2) 0.0087(3) -0.0206(3)
C6 0.0397(12) 0.0464(11) 0.0302(8) 0.0014(7) 0.0034(7) -0.0037(9)
C1 0.0334(11) 0.0405(10) 0.0273(8) 0.0020(7) 0.0046(7) 0.0012(8)
C2 0.0355(11) 0.0448(11) 0.0326(8) 0.0013(7) 0.0023(7) 0.0008(8)
C3 0.0473(14) 0.0484(12) 0.0380(9) -0.0054(8) 0.0015(8) 0.0076(10)
C4 0.0450(14) 0.0620(13) 0.0390(10) 0.0018(9) 0.0089(8) 0.0159(11)
C5 0.0336(11) 0.0649(14) 0.0373(9) 0.0076(9) 0.0059(7) -0.0008(10)
C7 0.0340(11) 0.0419(11) 0.0311(8) -0.0029(7) 0.0053(7) -0.0055(8)
O1 0.0556(9) 0.0562(9) 0.0303(6) 0.0008(5) 0.0118(5) 0.0005(7)
N1 0.0513(11) 0.0556(11) 0.0352(8) 0.0034(7) 0.0160(7) 0.0176(8)
O2 0.0393(9) 0.0515(8) 0.0479(7) -0.0090(6) 0.0100(5) 0.0066(6)
C8 0.0413(13) 0.0454(12) 0.0388(9) 0.0070(8) 0.0043(8) 0.0018(9)
O3 0.0641(11) 0.0633(10) 0.0776(10) -0.0170(8) -0.0030(8) -0.0062(8)
C9 0.0441(13) 0.0686(15) 0.0518(11) -0.0027(10) 0.0095(9) 0.0094(11)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Cl1 C2 1.7317(19) . ?
Cl2 C6 1.7393(18) . ?
C6 C5 1.383(3) . ?
C6 C1 1.383(2) . ?
C1 C2 1.391(2) . ?
C1 C7 1.506(2) . ?
C2 C3 1.381(3) . ?
C3 C4 1.378(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C7 O1 1.2235(19) . ?
C7 N1 1.323(2) . ?
N1 O2 1.4014(19) . ?
N1 H1N 0.81(2) . ?
O2 C8 1.381(2) . ?
C8 O3 1.178(2) . ?
C8 C9 1.485(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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
C5 C6 C1 122.38(17) . . ?
C5 C6 Cl2 119.21(14) . . ?
C1 C6 Cl2 118.39(13) . . ?
C2 C1 C6 117.37(15) . . ?
C2 C1 C7 122.56(15) . . ?
C6 C1 C7 119.77(15) . . ?
C3 C2 C1 121.53(17) . . ?
C3 C2 Cl1 119.56(15) . . ?
C1 C2 Cl1 118.90(13) . . ?
C2 C3 C4 119.10(18) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 121.27(18) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 118.35(18) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
O1 C7 N1 124.91(17) . . ?
O1 C7 C1 121.35(16) . . ?
N1 C7 C1 113.72(14) . . ?
C7 N1 O2 117.60(15) . . ?
C7 N1 H1N 124.4(15) . . ?
O2 N1 H1N 115.6(15) . . ?
C8 O2 N1 113.79(14) . . ?
O3 C8 O2 122.91(18) . . ?
O3 C8 C9 128.57(19) . . ?
O2 C8 C9 108.51(17) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.947
_diffrn_reflns_theta_full        24.49
_diffrn_measured_fraction_theta_full 0.947
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.069