# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2010

data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Sen, Subhabrata'
'Potti, Venkata'
'Surakanti, Ramu'
'Murthy, Y.L.'
'Raghavaiah, Pallepogu'

_publ_contact_author_name        'Sen, Subhabrata'
_publ_contact_author_email       organic6@hotmail.com

_publ_section_title              
;
Enantioselective synthesis of spirooxoindoles via chiral
auxiliary (bicyclic lactam) controlled SnAr reactions
;

data_egvk23
_database_code_depnum_ccdc_archive 'CCDC 796841'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 N3 O8'
_chemical_formula_weight         427.37

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'

_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_cell_setting           orthorhombic

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

_cell_length_a                   9.7745(6)
_cell_length_b                   9.7915(4)
_cell_length_c                   20.5118(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1963.12(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2664
_cell_measurement_theta_min      2.8704
_cell_measurement_theta_max      29.1412

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9623
_exptl_absorpt_correction_T_max  0.9732
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_chemical_absolute_configuration rm
_diffrn_ambient_temperature      293(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  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7779
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0797
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         26.37
_reflns_number_total             4020
_reflns_number_gt                2404
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_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^)+(0.0305P)^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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(11)
_refine_ls_number_reflns         4020
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.0733
_refine_ls_wR_factor_gt          0.0662
_refine_ls_goodness_of_fit_ref   0.833
_refine_ls_restrained_S_all      0.833
_refine_ls_shift/su_max          0.001
_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
C1 C 0.8616(3) 0.4824(2) 0.07051(10) 0.0416(7) Uani 1 1 d . . .
H1 H 0.7799 0.5233 0.0509 0.050 Uiso 1 1 calc R . .
C2 C 0.8680(3) 0.5650(2) 0.17911(11) 0.0445(7) Uani 1 1 d . . .
H2 H 0.9249 0.5369 0.2161 0.053 Uiso 1 1 calc R . .
C3 C 0.9546(4) 0.6530(3) 0.13159(13) 0.0714(9) Uani 1 1 d . . .
H3A H 0.9082 0.7383 0.1223 0.086 Uiso 1 1 calc R . .
H3B H 1.0429 0.6736 0.1508 0.086 Uiso 1 1 calc R . .
C4 C 0.8821(3) 0.3175(2) 0.15306(11) 0.0361(6) Uani 1 1 d . . .
C5 C 0.9127(2) 0.23881(19) 0.08825(10) 0.0315(6) Uani 1 1 d . . .
C6 C 0.9032(3) 0.35278(19) 0.03578(10) 0.0389(6) Uani 1 1 d . . .
H6A H 0.9909 0.3649 0.0145 0.047 Uiso 1 1 calc R . .
H6B H 0.8357 0.3288 0.0030 0.047 Uiso 1 1 calc R . .
C7 C 1.0607(3) 0.1886(2) 0.09716(11) 0.0410(6) Uani 1 1 d . . .
C8 C 1.1931(3) -0.0031(3) 0.12794(15) 0.0668(9) Uani 1 1 d . . .
H8A H 1.2199 -0.0411 0.0867 0.100 Uiso 1 1 calc R . .
H8B H 1.1877 -0.0746 0.1598 0.100 Uiso 1 1 calc R . .
H8C H 1.2595 0.0633 0.1415 0.100 Uiso 1 1 calc R . .
C9 C 0.8148(3) 0.1212(2) 0.07679(10) 0.0317(6) Uani 1 1 d . . .
C10 C 0.8167(3) 0.0375(2) 0.02106(9) 0.0327(6) Uani 1 1 d . . .
C11 C 0.7289(3) -0.0709(2) 0.01183(10) 0.0353(6) Uani 1 1 d . . .
H11 H 0.7363 -0.1265 -0.0248 0.042 Uiso 1 1 calc R . .
C12 C 0.6310(3) -0.0945(2) 0.05793(11) 0.0352(6) Uani 1 1 d . . .
C13 C 0.6186(3) -0.0131(2) 0.11212(11) 0.0441(6) Uani 1 1 d . . .
H13 H 0.5491 -0.0283 0.1422 0.053 Uiso 1 1 calc R . .
C14 C 0.7112(3) 0.0917(2) 0.12115(11) 0.0418(6) Uani 1 1 d . . .
H14 H 0.7040 0.1449 0.1586 0.050 Uiso 1 1 calc R . .
C15 C 0.7431(3) 0.6380(2) 0.20387(10) 0.0399(7) Uani 1 1 d . . .
C16 C 0.6126(3) 0.6023(2) 0.18590(11) 0.0462(7) Uani 1 1 d . . .
H16 H 0.5993 0.5307 0.1568 0.055 Uiso 1 1 calc R . .
C17 C 0.5003(3) 0.6718(2) 0.21062(13) 0.0597(8) Uani 1 1 d . . .
H17 H 0.4125 0.6466 0.1980 0.072 Uiso 1 1 calc R . .
C18 C 0.5185(4) 0.7774(3) 0.25360(14) 0.0681(9) Uani 1 1 d . . .
H18 H 0.4432 0.8237 0.2703 0.082 Uiso 1 1 calc R . .
C19 C 0.6486(4) 0.8143(3) 0.27181(13) 0.0740(11) Uani 1 1 d . . .
H19 H 0.6611 0.8861 0.3009 0.089 Uiso 1 1 calc R . .
C20 C 0.7611(4) 0.7460(2) 0.24740(12) 0.0611(9) Uani 1 1 d . . .
H20 H 0.8487 0.7720 0.2600 0.073 Uiso 1 1 calc R . .
N1 N 0.8389(2) 0.44571(16) 0.13781(7) 0.0351(5) Uani 1 1 d . . .
N2 N 0.9149(2) 0.05946(18) -0.03298(9) 0.0384(5) Uani 1 1 d . . .
N3 N 0.5350(3) -0.2068(2) 0.04769(10) 0.0443(5) Uani 1 1 d . . .
O1 O 0.9717(2) 0.57780(16) 0.07440(8) 0.0697(6) Uani 1 1 d . . .
O2 O 0.8969(2) 0.27289(15) 0.20755(7) 0.0489(5) Uani 1 1 d . . .
O3 O 1.16012(19) 0.25583(16) 0.08590(8) 0.0538(5) Uani 1 1 d . . .
O4 O 1.06093(18) 0.06171(15) 0.12150(8) 0.0495(5) Uani 1 1 d . . .
O5 O 1.0237(2) 0.11554(17) -0.02171(8) 0.0569(5) Uani 1 1 d . . .
O6 O 0.8811(2) 0.01798(15) -0.08664(7) 0.0528(5) Uani 1 1 d . . .
O7 O 0.5731(2) -0.30420(15) 0.01499(8) 0.0576(5) Uani 1 1 d . . .
O8 O 0.4214(2) -0.19718(17) 0.07225(9) 0.0625(5) 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
C1 0.0442(19) 0.0350(12) 0.0456(13) 0.0014(11) 0.0012(13) 0.0022(14)
C2 0.048(2) 0.0366(12) 0.0489(13) -0.0112(11) -0.0068(14) -0.0050(15)
C3 0.072(3) 0.0546(15) 0.087(2) -0.0184(16) 0.021(2) -0.0236(18)
C4 0.0336(16) 0.0353(12) 0.0394(13) -0.0037(11) -0.0012(12) -0.0041(13)
C5 0.0305(16) 0.0274(11) 0.0365(12) -0.0013(10) 0.0060(11) 0.0007(12)
C6 0.0439(18) 0.0367(12) 0.0362(12) 0.0027(10) 0.0036(12) -0.0016(13)
C7 0.0362(19) 0.0421(14) 0.0448(14) -0.0055(12) 0.0032(13) 0.0000(14)
C8 0.046(2) 0.0572(16) 0.098(2) -0.0044(16) -0.0062(17) 0.0198(17)
C9 0.0322(15) 0.0293(11) 0.0336(12) 0.0007(10) 0.0034(11) 0.0043(12)
C10 0.0334(16) 0.0311(12) 0.0336(12) 0.0028(11) 0.0042(11) 0.0068(12)
C11 0.0403(17) 0.0269(12) 0.0386(12) -0.0014(11) -0.0020(12) 0.0022(13)
C12 0.0313(15) 0.0264(11) 0.0479(14) 0.0020(11) -0.0058(12) -0.0024(12)
C13 0.0385(17) 0.0515(13) 0.0425(13) 0.0027(12) 0.0082(13) -0.0098(15)
C14 0.0418(18) 0.0445(14) 0.0390(13) -0.0092(12) 0.0048(12) -0.0056(14)
C15 0.055(2) 0.0314(12) 0.0332(13) -0.0017(11) -0.0025(14) 0.0030(14)
C16 0.054(2) 0.0347(12) 0.0502(14) -0.0072(11) 0.0084(15) -0.0014(16)
C17 0.057(2) 0.0507(16) 0.0716(17) -0.0044(15) 0.0177(17) -0.0027(17)
C18 0.084(3) 0.0582(18) 0.0625(17) -0.0016(16) 0.0244(19) 0.018(2)
C19 0.116(4) 0.0522(17) 0.0540(18) -0.0216(15) -0.005(2) 0.028(2)
C20 0.077(3) 0.0511(15) 0.0546(16) -0.0198(14) -0.0199(16) 0.0102(18)
N1 0.0404(14) 0.0288(10) 0.0361(10) -0.0058(9) 0.0010(9) 0.0032(10)
N2 0.0454(16) 0.0278(10) 0.0420(12) -0.0007(9) 0.0099(11) 0.0064(12)
N3 0.0396(16) 0.0357(11) 0.0577(13) 0.0074(11) -0.0089(12) -0.0037(13)
O1 0.0934(18) 0.0464(10) 0.0693(11) -0.0111(10) 0.0256(12) -0.0291(12)
O2 0.0654(14) 0.0442(9) 0.0370(8) 0.0017(8) -0.0038(9) 0.0013(10)
O3 0.0362(12) 0.0559(10) 0.0692(11) -0.0031(9) 0.0041(10) -0.0096(11)
O4 0.0381(12) 0.0390(9) 0.0715(10) 0.0067(8) 0.0014(9) 0.0073(9)
O5 0.0507(14) 0.0561(10) 0.0639(11) -0.0163(9) 0.0247(11) -0.0136(12)
O6 0.0638(14) 0.0604(10) 0.0340(8) -0.0044(8) 0.0050(10) 0.0123(11)
O7 0.0611(15) 0.0313(8) 0.0804(12) -0.0089(9) -0.0015(11) 0.0015(10)
O8 0.0382(13) 0.0557(10) 0.0937(14) -0.0068(10) 0.0057(11) -0.0119(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
C1 O1 1.427(3) . ?
C1 N1 1.443(3) . ?
C1 C6 1.511(3) . ?
C1 H1 0.9800 . ?
C2 N1 1.471(2) . ?
C2 C15 1.503(4) . ?
C2 C3 1.552(3) . ?
C2 H2 0.9800 . ?
C3 O1 1.395(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O2 1.209(2) . ?
C4 N1 1.361(3) . ?
C4 C5 1.565(3) . ?
C5 C9 1.516(3) . ?
C5 C7 1.539(3) . ?
C5 C6 1.553(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O3 1.196(3) . ?
C7 O4 1.339(3) . ?
C8 O4 1.446(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C14 1.392(3) . ?
C9 C10 1.407(3) . ?
C10 C11 1.377(3) . ?
C10 N2 1.482(3) . ?
C11 C12 1.365(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(3) . ?
C12 N3 1.461(3) . ?
C13 C14 1.380(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.373(4) . ?
C15 C20 1.395(3) . ?
C16 C17 1.387(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.370(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.380(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
N2 O6 1.219(2) . ?
N2 O5 1.219(3) . ?
N3 O8 1.223(3) . ?
N3 O7 1.224(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
O1 C1 N1 103.01(18) . . ?
O1 C1 C6 112.0(2) . . ?
N1 C1 C6 106.47(16) . . ?
O1 C1 H1 111.7 . . ?
N1 C1 H1 111.7 . . ?
C6 C1 H1 111.7 . . ?
N1 C2 C15 114.5(2) . . ?
N1 C2 C3 100.63(17) . . ?
C15 C2 C3 113.07(19) . . ?
N1 C2 H2 109.4 . . ?
C15 C2 H2 109.4 . . ?
C3 C2 H2 109.4 . . ?
O1 C3 C2 107.49(18) . . ?
O1 C3 H3A 110.2 . . ?
C2 C3 H3A 110.2 . . ?
O1 C3 H3B 110.2 . . ?
C2 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
O2 C4 N1 125.64(19) . . ?
O2 C4 C5 125.80(19) . . ?
N1 C4 C5 108.55(18) . . ?
C9 C5 C7 111.67(18) . . ?
C9 C5 C6 113.59(18) . . ?
C7 C5 C6 111.6(2) . . ?
C9 C5 C4 112.64(18) . . ?
C7 C5 C4 103.66(19) . . ?
C6 C5 C4 102.91(15) . . ?
C1 C6 C5 107.02(16) . . ?
C1 C6 H6A 110.3 . . ?
C5 C6 H6A 110.3 . . ?
C1 C6 H6B 110.3 . . ?
C5 C6 H6B 110.3 . . ?
H6A C6 H6B 108.6 . . ?
O3 C7 O4 125.6(2) . . ?
O3 C7 C5 124.4(2) . . ?
O4 C7 C5 110.0(2) . . ?
O4 C8 H8A 109.5 . . ?
O4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 114.8(2) . . ?
C14 C9 C5 121.08(19) . . ?
C10 C9 C5 124.1(2) . . ?
C11 C10 C9 123.6(2) . . ?
C11 C10 N2 114.34(19) . . ?
C9 C10 N2 122.1(2) . . ?
C12 C11 C10 118.1(2) . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
C11 C12 C13 121.6(2) . . ?
C11 C12 N3 118.6(2) . . ?
C13 C12 N3 119.8(2) . . ?
C12 C13 C14 118.8(2) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C13 C14 C9 122.9(2) . . ?
C13 C14 H14 118.5 . . ?
C9 C14 H14 118.5 . . ?
C16 C15 C20 118.8(3) . . ?
C16 C15 C2 122.9(2) . . ?
C20 C15 C2 118.3(3) . . ?
C15 C16 C17 120.8(2) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 119.5(3) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C20 120.7(3) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C19 C20 C15 119.9(3) . . ?
C19 C20 H20 120.0 . . ?
C15 C20 H20 120.0 . . ?
C4 N1 C1 113.66(17) . . ?
C4 N1 C2 122.72(17) . . ?
C1 N1 C2 108.88(16) . . ?
O6 N2 O5 123.9(2) . . ?
O6 N2 C10 116.8(2) . . ?
O5 N2 C10 119.3(2) . . ?
O8 N3 O7 124.2(2) . . ?
O8 N3 C12 117.8(2) . . ?
O7 N3 C12 118.0(2) . . ?
C3 O1 C1 107.6(2) . . ?
C7 O4 C8 116.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.036