# 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

_publ_contact_author_name        'Cehpuri Ramana'
_publ_contact_author_email       VR.CHEPURI@NCL.RES.IN

_publ_section_title              
;
Effect of the allylic substituents on ring closing
metathesis: The total synthesis of stagonolide B and 4-epi-stagonolide B
;
loop_
_publ_author_name
'Cehpuri Ramana'
'Awadut G. Giri'
'Mohabul A. Mondal'
'Vedavati G Puranik'

# Attachment 'CIF_CVR.cif'

data_4-epi-staganolideB
_database_code_depnum_ccdc_archive 'CCDC 743822'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          185-187
_chemical_formula_moiety         'C12 H20 O5'
_chemical_formula_sum            'C12 H20 O5'
_chemical_formula_weight         244.28
_chemical_absolute_configuration syn

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   C2

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

_cell_length_a                   16.861(15)
_cell_length_b                   4.981(4)
_cell_length_c                   16.109(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.087(14)
_cell_angle_gamma                90.00
_cell_volume                     1253.7(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    503
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      18.88

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9864
_exptl_absorpt_correction_T_max  0.9979
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      295(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'
_diffrn_measurement_method       'Phi and Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5114
_diffrn_reflns_av_R_equivalents  0.1106
_diffrn_reflns_av_sigmaI/netI    0.1956
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2177
_reflns_number_gt                948
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2003)'
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 2003)'

_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^)+(0.0761P)^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   5(3)
_refine_ls_number_reflns         2177
_refine_ls_number_parameters     158
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1490
_refine_ls_R_factor_gt           0.0720
_refine_ls_wR_factor_ref         0.1731
_refine_ls_wR_factor_gt          0.1554
_refine_ls_goodness_of_fit_ref   0.835
_refine_ls_restrained_S_all      0.835
_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
O1 O 0.2588(2) 0.6950(8) 0.2109(3) 0.0382(11) Uani 1 1 d . . .
O2 O 0.2028(3) 1.1014(9) 0.2140(4) 0.0595(15) Uani 1 1 d . . .
O3 O 0.0698(3) 0.7078(8) 0.4019(3) 0.0442(12) Uani 1 1 d . . .
H3' H 0.0616 0.8690 0.4052 0.066 Uiso 1 1 calc R . .
O4 O 0.3724(3) 1.0129(8) 0.4195(3) 0.0400(11) Uani 1 1 d . . .
H4' H 0.3913 1.0492 0.4730 0.060 Uiso 1 1 calc R . .
O5 O 0.4829(2) 0.7019(8) 0.3612(3) 0.0416(11) Uani 1 1 d . . .
H5' H 0.4937 0.8599 0.3752 0.062 Uiso 1 1 calc R . .
C1 C 0.1940(4) 0.8615(16) 0.2048(4) 0.0404(17) Uani 1 1 d . . .
C2 C 0.1124(3) 0.7182(13) 0.1852(4) 0.0394(16) Uani 1 1 d . . .
H2A H 0.1224 0.5265 0.1852 0.047 Uiso 1 1 calc R . .
H2B H 0.0728 0.7678 0.1259 0.047 Uiso 1 1 calc R . .
C3 C 0.0715(4) 0.7809(12) 0.2533(4) 0.0417(18) Uani 1 1 d . . .
H3A H 0.0681 0.9743 0.2583 0.050 Uiso 1 1 calc R . .
H3B H 0.0134 0.7117 0.2306 0.050 Uiso 1 1 calc R . .
C4 C 0.1188(4) 0.6654(13) 0.3467(4) 0.0378(16) Uani 1 1 d . . .
H4 H 0.1228 0.4709 0.3399 0.045 Uiso 1 1 calc R . .
C5 C 0.2070(4) 0.7689(12) 0.3863(4) 0.0377(17) Uani 1 1 d . . .
H5 H 0.2154 0.9408 0.4107 0.045 Uiso 1 1 calc R . .
C6 C 0.2751(4) 0.6297(11) 0.3892(4) 0.0355(17) Uani 1 1 d . . .
H6 H 0.2660 0.4470 0.3777 0.043 Uiso 1 1 calc R . .
C7 C 0.3634(4) 0.7232(12) 0.4079(4) 0.0387(16) Uani 1 1 d . . .
H7 H 0.4019 0.6363 0.4629 0.046 Uiso 1 1 calc R . .
C8 C 0.3928(3) 0.6572(12) 0.3335(4) 0.0335(15) Uani 1 1 d . . .
H8 H 0.3839 0.4639 0.3228 0.040 Uiso 1 1 calc R . .
C9 C 0.3460(4) 0.7943(12) 0.2434(4) 0.0370(17) Uani 1 1 d . . .
H9 H 0.3460 0.9890 0.2521 0.044 Uiso 1 1 calc R . .
C10 C 0.3813(4) 0.7322(14) 0.1735(4) 0.0453(17) Uani 1 1 d . . .
H10A H 0.3778 0.5398 0.1636 0.054 Uiso 1 1 calc R . .
H10B H 0.4414 0.7808 0.1967 0.054 Uiso 1 1 calc R . .
C11 C 0.3381(5) 0.8698(16) 0.0844(4) 0.063(2) Uani 1 1 d . . .
H11A H 0.3400 1.0624 0.0939 0.075 Uiso 1 1 calc R . .
H11B H 0.2784 0.8163 0.0595 0.075 Uiso 1 1 calc R . .
C12 C 0.3790(5) 0.805(2) 0.0172(5) 0.095(3) Uani 1 1 d . . .
H12A H 0.4402 0.8082 0.0468 0.142 Uiso 1 1 calc R . .
H12B H 0.3616 0.9361 -0.0299 0.142 Uiso 1 1 calc R . .
H12C H 0.3611 0.6299 -0.0076 0.142 Uiso 1 1 calc 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 0.036(2) 0.027(2) 0.048(2) 0.001(2) 0.011(2) 0.008(2)
O2 0.067(3) 0.017(3) 0.102(4) 0.006(3) 0.041(3) 0.009(2)
O3 0.049(3) 0.032(3) 0.062(3) 0.008(3) 0.032(2) 0.005(3)
O4 0.053(3) 0.026(2) 0.036(3) 0.000(2) 0.011(2) -0.006(2)
O5 0.033(2) 0.029(2) 0.062(3) -0.006(3) 0.017(2) -0.001(2)
C1 0.039(4) 0.050(5) 0.028(4) 0.010(4) 0.007(3) 0.000(4)
C2 0.042(4) 0.030(4) 0.043(4) -0.013(4) 0.013(3) 0.006(4)
C3 0.040(4) 0.028(4) 0.050(4) 0.001(3) 0.008(3) 0.000(3)
C4 0.050(4) 0.027(4) 0.042(4) -0.004(3) 0.024(3) 0.004(3)
C5 0.040(4) 0.030(4) 0.039(4) -0.004(3) 0.011(3) -0.001(3)
C6 0.042(4) 0.015(3) 0.047(4) 0.005(3) 0.014(3) 0.004(3)
C7 0.037(4) 0.029(4) 0.049(4) 0.008(4) 0.015(3) 0.005(3)
C8 0.036(4) 0.020(3) 0.047(4) 0.003(3) 0.017(3) 0.004(3)
C9 0.033(4) 0.028(4) 0.042(4) -0.004(3) 0.005(3) 0.002(3)
C10 0.042(4) 0.047(5) 0.049(4) 0.004(4) 0.019(3) 0.007(4)
C11 0.082(6) 0.061(5) 0.045(4) 0.007(4) 0.023(4) -0.004(4)
C12 0.100(7) 0.142(10) 0.057(5) 0.013(6) 0.047(5) -0.006(6)

_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 C1 1.346(8) . ?
O1 C9 1.450(7) . ?
O2 C1 1.207(8) . ?
O3 C4 1.439(6) . ?
O3 H3' 0.8200 . ?
O4 C7 1.456(7) . ?
O4 H4' 0.8200 . ?
O5 C8 1.431(6) . ?
O5 H5' 0.8200 . ?
C1 C2 1.476(9) . ?
C2 C3 1.531(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.526(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.473(7) . ?
C4 H4 0.9800 . ?
C5 C6 1.328(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.478(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.496(8) . ?
C7 H7 0.9800 . ?
C8 C9 1.527(8) . ?
C8 H8 0.9800 . ?
C9 C10 1.490(8) . ?
C9 H9 0.9800 . ?
C10 C11 1.508(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.521(10) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C1 O1 C9 120.1(5) . . ?
C4 O3 H3' 109.5 . . ?
C7 O4 H4' 109.5 . . ?
C8 O5 H5' 109.5 . . ?
O2 C1 O1 122.8(6) . . ?
O2 C1 C2 124.6(7) . . ?
O1 C1 C2 112.6(6) . . ?
C1 C2 C3 112.6(5) . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C2 114.8(5) . . ?
C4 C3 H3A 108.6 . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.5 . . ?
O3 C4 C5 113.6(5) . . ?
O3 C4 C3 110.2(5) . . ?
C5 C4 C3 111.4(5) . . ?
O3 C4 H4 107.1 . . ?
C5 C4 H4 107.1 . . ?
C3 C4 H4 107.1 . . ?
C6 C5 C4 123.4(5) . . ?
C6 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
C5 C6 C7 129.3(5) . . ?
C5 C6 H6 115.3 . . ?
C7 C6 H6 115.3 . . ?
O4 C7 C6 112.8(5) . . ?
O4 C7 C8 105.6(5) . . ?
C6 C7 C8 112.2(5) . . ?
O4 C7 H7 108.7 . . ?
C6 C7 H7 108.7 . . ?
C8 C7 H7 108.7 . . ?
O5 C8 C7 110.4(5) . . ?
O5 C8 C9 109.6(5) . . ?
C7 C8 C9 117.1(5) . . ?
O5 C8 H8 106.4 . . ?
C7 C8 H8 106.4 . . ?
C9 C8 H8 106.4 . . ?
O1 C9 C10 107.1(5) . . ?
O1 C9 C8 106.4(5) . . ?
C10 C9 C8 114.5(5) . . ?
O1 C9 H9 109.5 . . ?
C10 C9 H9 109.5 . . ?
C8 C9 H9 109.5 . . ?
C9 C10 C11 116.0(5) . . ?
C9 C10 H10A 108.3 . . ?
C11 C10 H10A 108.3 . . ?
C9 C10 H10B 108.3 . . ?
C11 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C10 C11 C12 113.3(6) . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O1 C1 O2 10.0(9) . . . . ?
C9 O1 C1 C2 -170.3(5) . . . . ?
O2 C1 C2 C3 -54.6(9) . . . . ?
O1 C1 C2 C3 125.7(6) . . . . ?
C1 C2 C3 C4 -69.8(8) . . . . ?
C2 C3 C4 O3 -173.0(5) . . . . ?
C2 C3 C4 C5 59.9(7) . . . . ?
O3 C4 C5 C6 133.4(6) . . . . ?
C3 C4 C5 C6 -101.5(7) . . . . ?
C4 C5 C6 C7 165.2(6) . . . . ?
C5 C6 C7 O4 -3.9(9) . . . . ?
C5 C6 C7 C8 -123.0(7) . . . . ?
O4 C7 C8 O5 68.2(6) . . . . ?
C6 C7 C8 O5 -168.6(5) . . . . ?
O4 C7 C8 C9 -58.1(6) . . . . ?
C6 C7 C8 C9 65.1(7) . . . . ?
C1 O1 C9 C10 -124.5(5) . . . . ?
C1 O1 C9 C8 112.5(5) . . . . ?
O5 C8 C9 O1 168.2(4) . . . . ?
C7 C8 C9 O1 -65.0(6) . . . . ?
O5 C8 C9 C10 50.1(7) . . . . ?
C7 C8 C9 C10 176.8(5) . . . . ?
O1 C9 C10 C11 63.8(7) . . . . ?
C8 C9 C10 C11 -178.5(5) . . . . ?
C9 C10 C11 C12 178.1(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.060