# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006


data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Sengodagounder Muthusamy'
_publ_contact_author_address     
;
School of Chemistry
Bharathidasan University
Palkalaiperur
Tiruchirappalli
620024
INDIA
;

_publ_contact_author_email       MUTHU@BDU.AC.IN

_publ_section_title              
;
Multicomponent reactions involving tricyclo-
oxonium ylide intermediate: Diastereoselective synthesis of mono- and
bisalkoxyoctahydro-1,4-benzodioxocin-6(5H)-one frameworks
;
loop_
_publ_author_name
'Sengodagounder Muthusamy'
'Janagiraman Krishnamurthi'
'Eringathodi Suresh'

# Attachment 'compound_11d_revised_suresh1.txt'

data_compound_11d
_database_code_depnum_ccdc_archive 'CCDC 619131'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H24 O6'
_chemical_formula_weight         348.38

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'
O O 0.0106 0.0060 '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                   9.6678(14)
_cell_length_b                   11.1324(17)
_cell_length_c                   16.858(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.138(3)
_cell_angle_gamma                90.00
_cell_volume                     1780.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Blocks
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_special_details           
;
?
;

_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  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8627
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0597
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3111
_reflns_number_gt                2016
_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    ORTEP
_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 w=1/[\s^2^(Fo^2^)+(0.0925P)^2^+0.1070P] 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_number_reflns         3111
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0649
_refine_ls_wR_factor_ref         0.1919
_refine_ls_wR_factor_gt          0.1588
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.126
_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3170(2) 0.27201(19) 0.02688(12) 0.0416(6) Uani 1 d . . .
C2 C 0.1971(3) 0.2687(3) 0.0654(2) 0.0445(8) Uani 1 d . . .
H2A H 0.2286 0.2536 0.1227 0.053 Uiso 1 calc R . .
H2B H 0.1358 0.2031 0.0430 0.053 Uiso 1 calc R . .
C3 C 0.1152(3) 0.3845(3) 0.0543(2) 0.0486(9) Uani 1 d . . .
H3A H 0.0827 0.3981 -0.0031 0.058 Uiso 1 calc R . .
H3B H 0.0326 0.3760 0.0786 0.058 Uiso 1 calc R . .
O4 O 0.1926(2) 0.48768(19) 0.08830(13) 0.0420(6) Uani 1 d . . .
C5 C 0.2465(3) 0.4768(3) 0.17210(18) 0.0385(8) Uani 1 d . . .
H5 H 0.1750 0.4387 0.1977 0.046 Uiso 1 calc R . .
C6 C 0.3824(3) 0.4023(3) 0.19108(19) 0.0341(7) Uani 1 d . . .
C6A C 0.4732(3) 0.3970(3) 0.12727(17) 0.0337(7) Uani 1 d . . .
H6A H 0.4458 0.4642 0.0900 0.040 Uiso 1 calc R . .
C7 C 0.6264(3) 0.4157(3) 0.1678(2) 0.0443(8) Uani 1 d . . .
H7A H 0.6543 0.3531 0.2077 0.053 Uiso 1 calc R . .
H7B H 0.6356 0.4923 0.1958 0.053 Uiso 1 calc R . .
C8 C 0.7248(4) 0.4137(4) 0.1071(2) 0.0594(10) Uani 1 d . . .
H8A H 0.7035 0.4809 0.0702 0.071 Uiso 1 calc R . .
H8B H 0.8217 0.4215 0.1355 0.071 Uiso 1 calc R . .
C9 C 0.7066(4) 0.2967(4) 0.0601(2) 0.0612(11) Uani 1 d . . .
H9A H 0.7371 0.2304 0.0966 0.073 Uiso 1 calc R . .
H9B H 0.7657 0.2979 0.0197 0.073 Uiso 1 calc R . .
C10 C 0.5522(4) 0.2769(3) 0.0182(2) 0.0502(9) Uani 1 d . . .
H10A H 0.5251 0.3385 -0.0225 0.060 Uiso 1 calc R . .
H10B H 0.5438 0.1997 -0.0089 0.060 Uiso 1 calc R . .
C10A C 0.4527(3) 0.2806(3) 0.07740(18) 0.0365(8) Uani 1 d . . .
O11 O 0.4737(2) 0.18610(18) 0.13441(12) 0.0398(6) Uani 1 d . . .
C12 C 0.4545(4) 0.0667(3) 0.1025(2) 0.0575(10) Uani 1 d . . .
H12A H 0.3644 0.0609 0.0669 0.086 Uiso 1 calc R . .
H12B H 0.4586 0.0105 0.1461 0.086 Uiso 1 calc R . .
H12C H 0.5277 0.0486 0.0731 0.086 Uiso 1 calc R . .
O13 O 0.4154(2) 0.3554(2) 0.25650(13) 0.0441(6) Uani 1 d . . .
C14 C 0.2798(3) 0.6018(3) 0.2093(2) 0.0408(8) Uani 1 d . . .
H14 H 0.2977 0.5936 0.2683 0.049 Uiso 1 calc R . .
O15 O 0.4053(2) 0.6421(2) 0.18644(15) 0.0505(6) Uani 1 d . . .
H15 H 0.4469 0.6881 0.2209 0.076 Uiso 1 calc R . .
C16 C 0.1558(3) 0.6867(3) 0.18437(19) 0.0400(8) Uani 1 d . . .
C17 C 0.1663(4) 0.7850(3) 0.1368(2) 0.0470(9) Uani 1 d . . .
H17 H 0.2511 0.8007 0.1205 0.056 Uiso 1 calc R . .
C18 C 0.0531(4) 0.8611(3) 0.1127(2) 0.0540(10) Uani 1 d . . .
H18 H 0.0625 0.9283 0.0815 0.065 Uiso 1 calc R . .
C19 C -0.0721(4) 0.8374(3) 0.1348(2) 0.0505(9) Uani 1 d . . .
C20 C -0.0835(4) 0.7394(4) 0.1827(2) 0.0596(11) Uani 1 d . . .
H20 H -0.1690 0.7233 0.1981 0.071 Uiso 1 calc R . .
C21 C 0.0296(4) 0.6649(3) 0.2081(2) 0.0543(10) Uani 1 d . . .
H21 H 0.0210 0.5998 0.2414 0.065 Uiso 1 calc R . .
C22 C -0.1969(3) 0.9146(3) 0.10660(17) 0.0674(12) Uani 1 d . . .
H22 H -0.2818 0.8932 0.1208 0.081 Uiso 1 calc R . .
O23 O -0.1941(3) 1.0031(3) 0.06648(17) 0.0944(11) Uani 1 d R . .

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
O1 0.0409(13) 0.0465(14) 0.0357(11) -0.0058(10) 0.0034(10) 0.0059(10)
C2 0.039(2) 0.044(2) 0.0483(19) -0.0078(16) 0.0031(16) -0.0017(15)
C3 0.0337(18) 0.053(2) 0.055(2) -0.0143(18) -0.0023(16) 0.0035(16)
O4 0.0411(13) 0.0404(13) 0.0412(13) -0.0061(10) -0.0002(10) 0.0073(10)
C5 0.0394(19) 0.0397(19) 0.0363(17) -0.0013(15) 0.0071(15) 0.0046(15)
C6 0.0362(18) 0.0299(17) 0.0352(17) -0.0031(14) 0.0043(14) 0.0011(13)
C6A 0.0319(17) 0.0343(17) 0.0350(17) 0.0002(13) 0.0067(13) 0.0063(13)
C7 0.0355(19) 0.0430(19) 0.054(2) -0.0039(16) 0.0081(16) 0.0017(15)
C8 0.044(2) 0.061(2) 0.077(3) -0.007(2) 0.021(2) -0.0041(18)
C9 0.052(2) 0.071(3) 0.067(3) -0.007(2) 0.030(2) 0.006(2)
C10 0.055(2) 0.051(2) 0.048(2) -0.0041(17) 0.0186(18) 0.0055(18)
C10A 0.0353(18) 0.0381(18) 0.0355(17) 0.0002(14) 0.0055(14) 0.0055(14)
O11 0.0442(13) 0.0331(12) 0.0406(12) 0.0006(10) 0.0040(10) 0.0059(10)
C12 0.066(3) 0.037(2) 0.064(2) -0.0026(18) -0.003(2) 0.0059(18)
O13 0.0455(14) 0.0502(14) 0.0362(12) 0.0035(11) 0.0071(10) 0.0092(11)
C14 0.0366(19) 0.045(2) 0.0397(18) -0.0081(15) 0.0046(15) 0.0084(15)
O15 0.0332(13) 0.0485(15) 0.0691(16) -0.0169(12) 0.0084(12) -0.0020(10)
C16 0.0381(19) 0.0409(19) 0.0396(18) -0.0089(15) 0.0038(15) 0.0072(15)
C17 0.0395(19) 0.048(2) 0.052(2) -0.0050(18) 0.0063(16) 0.0036(16)
C18 0.054(2) 0.045(2) 0.060(2) 0.0001(18) 0.0036(19) 0.0067(18)
C19 0.052(2) 0.050(2) 0.047(2) -0.0096(18) 0.0038(18) 0.0192(18)
C20 0.042(2) 0.073(3) 0.069(3) -0.007(2) 0.0224(19) 0.0152(19)
C21 0.046(2) 0.059(2) 0.061(2) 0.0050(19) 0.0202(19) 0.0136(18)
C22 0.074(3) 0.069(3) 0.055(2) -0.013(2) 0.001(2) 0.030(2)
O23 0.096(3) 0.070(2) 0.108(3) 0.006(2) -0.006(2) 0.0385(18)

_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
O1 C10A 1.423(4) . ?
O1 C2 1.434(4) . ?
C2 C3 1.505(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O4 1.429(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
O4 C5 1.413(4) . ?
C5 C6 1.534(4) . ?
C5 C14 1.535(4) . ?
C5 H5 0.9800 . ?
C6 O13 1.206(3) . ?
C6 C6A 1.516(4) . ?
C6A C7 1.521(4) . ?
C6A C10A 1.537(4) . ?
C6A H6A 0.9800 . ?
C7 C8 1.525(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.517(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.540(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C10A 1.515(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10A O11 1.413(4) . ?
O11 C12 1.433(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 O15 1.416(4) . ?
C14 C16 1.521(4) . ?
C14 H14 0.9800 . ?
O15 H15 0.8200 . ?
C16 C17 1.372(5) . ?
C16 C21 1.377(5) . ?
C17 C18 1.381(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.359(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.375(5) . ?
C19 C22 1.483(4) . ?
C20 C21 1.373(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 O23 1.1980 . ?
C22 H22 0.9300 . ?

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
C10A O1 C2 117.6(2) . . ?
O1 C2 C3 111.9(3) . . ?
O1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
O1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
O4 C3 C2 114.6(3) . . ?
O4 C3 H3A 108.6 . . ?
C2 C3 H3A 108.6 . . ?
O4 C3 H3B 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C5 O4 C3 113.3(2) . . ?
O4 C5 C6 113.0(2) . . ?
O4 C5 C14 109.8(2) . . ?
C6 C5 C14 107.5(2) . . ?
O4 C5 H5 108.8 . . ?
C6 C5 H5 108.8 . . ?
C14 C5 H5 108.8 . . ?
O13 C6 C6A 123.0(3) . . ?
O13 C6 C5 119.3(3) . . ?
C6A C6 C5 117.6(3) . . ?
C6 C6A C7 108.9(2) . . ?
C6 C6A C10A 112.9(2) . . ?
C7 C6A C10A 111.9(2) . . ?
C6 C6A H6A 107.6 . . ?
C7 C6A H6A 107.6 . . ?
C10A C6A H6A 107.6 . . ?
C6A C7 C8 112.1(3) . . ?
C6A C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C6A C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7 109.8(3) . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C8 C9 C10 111.5(3) . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C10A C10 C9 112.1(3) . . ?
C10A C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C10A C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
O11 C10A O1 110.6(2) . . ?
O11 C10A C10 113.7(3) . . ?
O1 C10A C10 103.5(2) . . ?
O11 C10A C6A 105.6(2) . . ?
O1 C10A C6A 113.0(2) . . ?
C10 C10A C6A 110.6(3) . . ?
C10A O11 C12 116.4(2) . . ?
O11 C12 H12A 109.5 . . ?
O11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O15 C14 C16 113.5(3) . . ?
O15 C14 C5 107.4(2) . . ?
C16 C14 C5 111.0(3) . . ?
O15 C14 H14 108.3 . . ?
C16 C14 H14 108.3 . . ?
C5 C14 H14 108.3 . . ?
C14 O15 H15 109.5 . . ?
C17 C16 C21 118.7(3) . . ?
C17 C16 C14 120.9(3) . . ?
C21 C16 C14 120.4(3) . . ?
C16 C17 C18 121.1(3) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C19 C18 C17 119.8(4) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 119.5(3) . . ?
C18 C19 C22 120.8(3) . . ?
C20 C19 C22 119.7(3) . . ?
C21 C20 C19 120.9(4) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C16 120.0(4) . . ?
C20 C21 H21 120.0 . . ?
C16 C21 H21 120.0 . . ?
O23 C22 C19 123.5(2) . . ?
O23 C22 H22 118.2 . . ?
C19 C22 H22 118.2 . . ?

_diffrn_measured_fraction_theta_max 0.939
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.939
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.082