# Supplementary Material (ESI) for Green Chemistry
# This journal is © The Royal Society of Chemistry 2008

data_global
_journal_name_full               'Green Chemistry'

_journal_coden_Cambridge         1048
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'P. Chattopadhyay'
_publ_contact_author_email       PARTHA@IICB.RES.IN

_publ_section_title              
;
A Green Chemical Approach for the N-alkylation of
Aldoximes to form Nitrones in Organized Aqueous Media and Their In Situ
Cycloaddition with Olefins
;
loop_
_publ_author_name
'P. Chattopadhyay'
'Pranab K. Bhattacharya'
'Amrita Chatterje'
'Sandip K. Hota'

# Attachment 'SH110A.cif.txt'

data_sh110a
_database_code_depnum_ccdc_archive 'CCDC 686184'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H13 N O3 S'
_chemical_formula_weight         239.28

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   17.1392(5)
_cell_length_b                   6.0512(2)
_cell_length_c                   10.9857(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.007(2)
_cell_angle_gamma                90.00
_cell_volume                     1137.79(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2660
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      30.870

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.994
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa Apex 2'
_diffrn_measurement_method       'Difference vectors'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17365
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.19
_diffrn_reflns_theta_max         30.87
_reflns_number_total             3520
_reflns_number_gt                2660
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex 2, Bruker Kappa'
_computing_cell_refinement       'Apex 2, Bruker Kappa'
_computing_data_reduction        'Apex 2, Bruker Kappa'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  ?

_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^)+(0.1000P)^2^+0.0000P] 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         3520
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1748
_refine_ls_wR_factor_gt          0.1500
_refine_ls_goodness_of_fit_ref   1.241
_refine_ls_restrained_S_all      1.241
_refine_ls_shift/su_max          0.000
_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
S1 S 0.89052(2) 0.64753(6) 0.08819(3) 0.03701(17) Uani 1 1 d . . .
C10 C 0.78895(9) 0.6434(2) 0.11815(15) 0.0382(3) Uani 1 1 d . . .
H10 H 0.7618 0.7760 0.0871 0.046 Uiso 1 1 calc R . .
C6 C 0.69961(9) 0.6647(2) 0.29597(16) 0.0397(4) Uani 1 1 d . . .
C7 C 0.78071(9) 0.6129(2) 0.25598(14) 0.0354(3) Uani 1 1 d . . .
H7 H 0.8193 0.7045 0.3016 0.042 Uiso 1 1 calc R . .
C9 C 0.92138(10) 0.3899(3) 0.14791(17) 0.0450(4) Uani 1 1 d . . .
H9A H 0.9070 0.2746 0.0896 0.054 Uiso 1 1 calc R . .
H9B H 0.9778 0.3898 0.1601 0.054 Uiso 1 1 calc R . .
C8 C 0.88502(11) 0.3398(3) 0.26880(19) 0.0511(5) Uani 1 1 d . . .
H8A H 0.8954 0.1863 0.2893 0.061 Uiso 1 1 calc R . .
H8B H 0.9112 0.4296 0.3317 0.061 Uiso 1 1 calc R . .
C11 C 0.75106(11) 0.4345(4) 0.06880(19) 0.0572(5) Uani 1 1 d . . .
H11A H 0.6957 0.4576 0.0500 0.069 Uiso 1 1 calc R . .
H11B H 0.7753 0.3868 -0.0046 0.069 Uiso 1 1 calc R . .
C5 C 0.66559(12) 0.8660(3) 0.2734(2) 0.0652(6) Uani 1 1 d . . .
H5 H 0.6921 0.9705 0.2293 0.078 Uiso 1 1 calc R . .
C1 C 0.65967(12) 0.5188(4) 0.3654(3) 0.0768(7) Uani 1 1 d . . .
H1 H 0.6817 0.3821 0.3851 0.092 Uiso 1 1 calc R . .
C2 C 0.58759(17) 0.5719(5) 0.4063(4) 0.1098(13) Uani 1 1 d . . .
H2 H 0.5613 0.4697 0.4524 0.132 Uiso 1 1 calc R . .
C3 C 0.55423(13) 0.7699(4) 0.3806(3) 0.0807(7) Uani 1 1 d . . .
H3 H 0.5053 0.8038 0.4082 0.097 Uiso 1 1 calc R . .
C4 C 0.59313(13) 0.9187(4) 0.3141(3) 0.0745(7) Uani 1 1 d . . .
H4 H 0.5710 1.0559 0.2960 0.089 Uiso 1 1 calc R . .
O2 O 0.89876(8) 0.6476(2) -0.04122(12) 0.0591(4) Uani 1 1 d . . .
O3 O 0.92705(7) 0.82305(18) 0.15789(13) 0.0527(3) Uani 1 1 d . . .
O1 O 0.76300(8) 0.2734(2) 0.16400(14) 0.0624(4) Uani 1 1 d . . .
N1 N 0.80037(9) 0.3779(2) 0.27213(15) 0.0463(4) Uani 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
S1 0.0347(2) 0.0454(2) 0.0314(3) 0.00544(13) 0.00581(17) -0.00174(13)
C10 0.0322(8) 0.0489(8) 0.0334(9) 0.0036(6) 0.0001(6) 0.0006(5)
C6 0.0344(8) 0.0445(7) 0.0406(9) -0.0008(6) 0.0072(7) -0.0035(6)
C7 0.0339(8) 0.0385(6) 0.0343(8) 0.0030(5) 0.0058(6) -0.0036(5)
C9 0.0412(9) 0.0485(8) 0.0463(10) 0.0064(7) 0.0119(7) 0.0077(6)
C8 0.0452(10) 0.0562(9) 0.0530(12) 0.0206(8) 0.0139(8) 0.0129(7)
C11 0.0445(10) 0.0752(11) 0.0517(12) -0.0137(9) 0.0003(8) -0.0147(9)
C5 0.0566(12) 0.0461(9) 0.0956(19) 0.0112(9) 0.0310(12) 0.0023(7)
C1 0.0583(13) 0.0710(13) 0.1055(19) 0.0372(12) 0.0450(12) 0.0152(10)
C2 0.0797(17) 0.0888(16) 0.169(3) 0.047(2) 0.083(2) 0.0169(15)
C3 0.0487(12) 0.0753(13) 0.122(2) -0.0043(15) 0.0383(13) 0.0035(10)
C4 0.0586(12) 0.0598(10) 0.107(2) 0.0056(12) 0.0258(12) 0.0156(10)
O2 0.0540(8) 0.0914(10) 0.0329(7) 0.0127(6) 0.0110(6) 0.0064(6)
O3 0.0456(7) 0.0498(6) 0.0635(9) -0.0044(5) 0.0102(6) -0.0122(5)
O1 0.0586(8) 0.0464(6) 0.0832(10) -0.0111(6) 0.0135(7) -0.0191(6)
N1 0.0441(8) 0.0445(7) 0.0516(9) 0.0096(6) 0.0140(7) 0.0015(5)

_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
S1 O3 1.4339(12) . ?
S1 O2 1.4360(14) . ?
S1 C9 1.7618(16) . ?
S1 C10 1.7887(16) . ?
C10 C11 1.509(2) . ?
C10 C7 1.539(2) . ?
C6 C5 1.368(2) . ?
C6 C1 1.373(2) . ?
C6 C7 1.512(2) . ?
C7 N1 1.4702(18) . ?
C9 C8 1.527(2) . ?
C8 N1 1.471(2) . ?
C11 O1 1.436(3) . ?
C5 C4 1.379(3) . ?
C1 C2 1.374(3) . ?
C2 C3 1.351(4) . ?
C3 C4 1.356(3) . ?
O1 N1 1.463(2) . ?

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
O3 S1 O2 117.74(9) . . ?
O3 S1 C9 110.03(8) . . ?
O2 S1 C9 109.02(8) . . ?
O3 S1 C10 108.30(7) . . ?
O2 S1 C10 109.23(8) . . ?
C9 S1 C10 101.25(7) . . ?
C11 C10 C7 101.14(12) . . ?
C11 C10 S1 110.51(12) . . ?
C7 C10 S1 108.85(10) . . ?
C5 C6 C1 116.95(16) . . ?
C5 C6 C7 121.42(14) . . ?
C1 C6 C7 121.41(14) . . ?
N1 C7 C6 111.93(12) . . ?
N1 C7 C10 101.66(12) . . ?
C6 C7 C10 113.22(13) . . ?
C8 C9 S1 111.81(11) . . ?
N1 C8 C9 116.00(15) . . ?
O1 C11 C10 105.35(14) . . ?
C6 C5 C4 121.99(18) . . ?
C6 C1 C2 120.9(2) . . ?
C3 C2 C1 121.1(2) . . ?
C2 C3 C4 119.1(2) . . ?
C3 C4 C5 119.8(2) . . ?
C11 O1 N1 109.72(11) . . ?
O1 N1 C7 103.43(13) . . ?
O1 N1 C8 107.59(13) . . ?
C7 N1 C8 111.64(12) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        30.87
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.130