# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2011

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Faber, Jonathan'
_publ_contact_author_email       c.williams3@uq.edu.au

_publ_section_title              
;
A Concise Total Synthesis
of (+-)-Cipadonoid B from Synthetic Azedaralide
;
_publ_requested_category         FO
loop_
_publ_author_name
J.Faber
C.Williams

# Attachment '- archive.cif'

#\#CIF_1.1

# CIF produced by WinGX routine CIF_UPDATE
# Created on 2010-07-07 at 16:44:12
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.3
# Request file : c:\wingx\files\archive.dat
# CIF files read : 397jf3 397jf3 struct

data_397jf3
_database_code_depnum_ccdc_archive 'CCDC 798654'
#TrackingRef '- archive.cif'

_audit_creation_date             2010-07-07T16:44:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C27 H32 O6'
_chemical_formula_sum            'C27 H32 O6'
_chemical_formula_weight         452.53
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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                   8.4670(6)
_cell_length_b                   26.236(2)
_cell_length_c                   11.2916(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.651(7)
_cell_angle_gamma                90
_cell_volume                     2376.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2936
_cell_measurement_theta_min      2.9696
_cell_measurement_theta_max      29.0102
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_number            10315
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             4171
_reflns_number_gt                2231
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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^)+(0.0478P)^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     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_coef       0.0031(6)
_refine_ls_number_reflns         4171
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0889
_refine_ls_goodness_of_fit_ref   0.838
_refine_ls_restrained_S_all      0.838
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.029

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 1.0277(2) 0.08798(7) 0.33944(17) 0.0370(5) Uani 1 1 d . . .
C2 C 1.1105(2) 0.13976(7) 0.37127(18) 0.0361(5) Uani 1 1 d . . .
C3 C 1.1002(2) 0.17295(7) 0.27987(18) 0.0428(5) Uani 1 1 d . . .
H3 H 1.1618 0.2029 0.2989 0.051 Uiso 1 1 calc R . .
C4 C 0.9964(3) 0.16412(8) 0.1514(2) 0.0465(5) Uani 1 1 d . . .
C6 C 1.0178(2) 0.07543(6) 0.20485(18) 0.0426(5) Uani 1 1 d . . .
H6 H 1.1318 0.0711 0.2026 0.051 Uiso 1 1 calc R . .
C7 C 1.1350(2) 0.04673(7) 0.42551(17) 0.0466(6) Uani 1 1 d . . .
H7A H 1.0714 0.0153 0.4146 0.056 Uiso 1 1 calc R . .
H7B H 1.2326 0.0403 0.4005 0.056 Uiso 1 1 calc R . .
C8 C 1.1912(3) 0.06147(7) 0.56357(18) 0.0529(6) Uani 1 1 d . . .
H8A H 1.2627 0.0347 0.6113 0.063 Uiso 1 1 calc R . .
H8B H 1.0939 0.0633 0.591 0.063 Uiso 1 1 calc R . .
C9 C 1.2851(2) 0.11237(6) 0.59357(17) 0.0401(5) Uani 1 1 d . . .
H9 H 1.28 0.1221 0.676 0.048 Uiso 1 1 calc R . .
C10 C 1.1859(2) 0.15281(7) 0.50519(17) 0.0373(5) Uani 1 1 d . . .
C11 C 1.5821(3) 0.17224(8) 0.4648(2) 0.0568(6) Uani 1 1 d . . .
H11 H 1.5629 0.1854 0.3849 0.068 Uiso 1 1 calc R . .
C12 C 1.6860(3) 0.19612(8) 0.5606(2) 0.0587(6) Uani 1 1 d . . .
H12 H 1.7451 0.2236 0.5439 0.07 Uiso 1 1 calc R . .
C13 C 1.7161(2) 0.18233(7) 0.69446(18) 0.0439(5) Uani 1 1 d . . .
C14 C 1.5576(2) 0.15633(7) 0.70456(16) 0.0370(5) Uani 1 1 d . . .
H14 H 1.4738 0.1835 0.6851 0.044 Uiso 1 1 calc R . .
C15 C 1.4781(2) 0.11341(7) 0.60726(17) 0.0394(5) Uani 1 1 d . . .
C16 C 1.4969(2) 0.12631(8) 0.47968(19) 0.0466(6) Uani 1 1 d . . .
C17 C 0.7130(4) -0.02410(10) 0.0598(3) 0.0879(10) Uani 1 1 d . . .
H17 H 0.6067 -0.0373 0.0224 0.106 Uiso 1 1 calc R . .
C18 C 0.7480(3) 0.02335(9) 0.0974(2) 0.0839(9) Uani 1 1 d . . .
H18 H 0.6703 0.0492 0.09 0.101 Uiso 1 1 calc R . .
C19 C 0.9213(3) 0.02861(8) 0.15046(19) 0.0503(6) Uani 1 1 d . . .
C20 C 0.9832(3) -0.01790(9) 0.1409(2) 0.0766(8) Uani 1 1 d . . .
H20 H 1.096 -0.026 0.1692 0.092 Uiso 1 1 calc R . .
C22 C 1.1530(2) 0.19816(7) 0.5449(2) 0.0530(6) Uani 1 1 d . . .
H22A H 1.0839 0.221 0.4888 0.064 Uiso 1 1 calc R . .
H22B H 1.1992 0.207 0.6286 0.064 Uiso 1 1 calc R . .
C24 C 1.5748(3) 0.14078(8) 0.83967(17) 0.0481(5) Uani 1 1 d . . .
H24A H 1.5539 0.1045 0.8409 0.058 Uiso 1 1 calc R . .
H24B H 1.6891 0.1467 0.8914 0.058 Uiso 1 1 calc R . .
C25 C 1.5590(3) 0.06067(7) 0.6435(2) 0.0702(8) Uani 1 1 d . . .
H25A H 1.5507 0.0507 0.7231 0.105 Uiso 1 1 calc R . .
H25B H 1.6743 0.0623 0.6486 0.105 Uiso 1 1 calc R . .
H25C H 1.5025 0.0361 0.5814 0.105 Uiso 1 1 calc R . .
C27 C 1.7451(3) 0.23216(8) 0.7707(2) 0.0640(7) Uani 1 1 d . . .
H27A H 1.764 0.2244 0.8572 0.096 Uiso 1 1 calc R . .
H27B H 1.6487 0.2536 0.7404 0.096 Uiso 1 1 calc R . .
H27C H 1.8406 0.2495 0.762 0.096 Uiso 1 1 calc R . .
C28 C 1.8768(3) 0.15003(9) 0.7403(2) 0.0675(7) Uani 1 1 d . . .
H28A H 1.8969 0.1405 0.826 0.101 Uiso 1 1 calc R . .
H28B H 1.9693 0.1696 0.7336 0.101 Uiso 1 1 calc R . .
H28C H 1.8641 0.1199 0.6899 0.101 Uiso 1 1 calc R . .
C29 C 1.4618(3) 0.16785(9) 0.8979(2) 0.0498(6) Uani 1 1 d . . .
C32 C 1.3633(4) 0.16752(12) 1.0709(3) 0.1048(10) Uani 1 1 d . . .
H32A H 1.3778 0.1491 1.1472 0.157 Uiso 1 1 calc R . .
H32B H 1.249 0.1653 1.0189 0.157 Uiso 1 1 calc R . .
H32C H 1.3929 0.2026 1.0898 0.157 Uiso 1 1 calc R . .
C33 C 0.8547(3) 0.09153(8) 0.3556(2) 0.0595(6) Uani 1 1 d . . .
H33A H 0.7992 0.0592 0.3359 0.089 Uiso 1 1 calc R . .
H33B H 0.7901 0.1172 0.3006 0.089 Uiso 1 1 calc R . .
H33C H 0.8667 0.1004 0.4406 0.089 Uiso 1 1 calc R . .
O5 O 0.93960(17) 0.11653(5) 0.11909(12) 0.0511(4) Uani 1 1 d . . .
O21 O 0.8606(3) -0.05118(7) 0.08501(17) 0.1107(8) Uani 1 1 d . . .
O23 O 0.95111(19) 0.19736(5) 0.07361(14) 0.0658(5) Uani 1 1 d . . .
O26 O 1.44534(19) 0.09722(6) 0.39112(14) 0.0752(5) Uani 1 1 d . . .
O30 O 1.3769(2) 0.20405(7) 0.85654(15) 0.0819(6) Uani 1 1 d . . .
O31 O 1.46947(19) 0.14561(6) 1.00594(14) 0.0710(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 0.0361(12) 0.0350(11) 0.0397(12) -0.0023(9) 0.0117(9) -0.0031(9)
C2 0.0314(11) 0.0352(11) 0.0434(12) -0.0007(10) 0.0141(9) 0.0036(9)
C3 0.0450(13) 0.0351(12) 0.0475(13) 0.0006(10) 0.0137(10) -0.0006(10)
C4 0.0494(14) 0.0414(13) 0.0488(14) 0.0055(12) 0.0157(11) 0.0061(11)
C6 0.0409(13) 0.0371(12) 0.0445(13) 0.0011(10) 0.0064(10) 0.0053(10)
C7 0.0521(14) 0.0320(11) 0.0487(13) 0.0034(10) 0.0063(10) -0.0102(10)
C8 0.0600(15) 0.0468(13) 0.0460(13) 0.0102(10) 0.0088(10) -0.0104(11)
C9 0.0439(13) 0.0413(12) 0.0352(11) 0.0000(9) 0.0127(9) -0.0040(10)
C10 0.0345(12) 0.0344(11) 0.0441(12) -0.0024(10) 0.0142(9) -0.0032(9)
C11 0.0749(17) 0.0611(15) 0.0358(13) 0.0036(11) 0.0199(12) -0.0007(13)
C12 0.0749(17) 0.0558(14) 0.0503(15) 0.0065(12) 0.0271(12) -0.0107(13)
C13 0.0461(14) 0.0473(12) 0.0387(12) -0.0035(10) 0.0140(10) -0.0046(11)
C14 0.0390(12) 0.0390(11) 0.0313(11) -0.0031(9) 0.0087(9) 0.0038(9)
C15 0.0396(13) 0.0375(11) 0.0388(12) -0.0024(9) 0.0094(9) 0.0057(9)
C16 0.0353(13) 0.0628(15) 0.0395(13) -0.0127(12) 0.0088(10) 0.0093(11)
C17 0.0585(18) 0.0590(17) 0.113(2) -0.0156(16) -0.0187(16) -0.0132(15)
C18 0.0587(19) 0.0624(17) 0.108(2) -0.0157(15) -0.0043(16) -0.0036(14)
C19 0.0528(15) 0.0425(13) 0.0452(13) -0.0021(11) 0.0012(11) 0.0013(11)
C20 0.0701(18) 0.0496(15) 0.0806(18) -0.0174(13) -0.0174(14) 0.0046(14)
C22 0.0497(14) 0.0503(14) 0.0525(14) -0.0073(11) 0.0073(11) 0.0089(11)
C24 0.0497(14) 0.0562(13) 0.0378(12) 0.0004(10) 0.0132(10) 0.0007(11)
C25 0.0693(17) 0.0473(14) 0.0767(17) -0.0085(12) -0.0009(13) 0.0142(12)
C27 0.0714(17) 0.0626(15) 0.0532(14) -0.0096(12) 0.0134(12) -0.0169(12)
C28 0.0458(15) 0.0884(18) 0.0710(17) 0.0060(13) 0.0222(12) 0.0024(13)
C29 0.0517(15) 0.0611(15) 0.0350(13) -0.0093(12) 0.0118(10) -0.0057(12)
C32 0.111(3) 0.155(3) 0.070(2) -0.0187(18) 0.0595(18) -0.001(2)
C33 0.0452(14) 0.0675(15) 0.0681(16) -0.0065(12) 0.0213(11) -0.0098(11)
O5 0.0598(10) 0.0418(9) 0.0427(8) 0.0029(7) 0.0039(7) 0.0027(7)
O21 0.1287(19) 0.0607(11) 0.1066(16) -0.0155(11) -0.0130(14) -0.0092(13)
O23 0.0876(12) 0.0507(9) 0.0522(10) 0.0172(8) 0.0126(8) 0.0059(8)
O26 0.0656(11) 0.1100(13) 0.0563(11) -0.0410(10) 0.0282(8) -0.0222(9)
O30 0.1040(15) 0.0908(13) 0.0560(11) -0.0036(9) 0.0326(10) 0.0336(11)
O31 0.0813(12) 0.0954(12) 0.0478(10) 0.0006(9) 0.0367(8) -0.0036(9)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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 C2 1.518(2) . ?
C1 C6 1.531(3) . ?
C1 C33 1.535(3) . ?
C1 C7 1.542(2) . ?
C2 C3 1.332(2) . ?
C2 C10 1.481(3) . ?
C3 C4 1.454(3) . ?
C4 O23 1.210(2) . ?
C4 O5 1.346(2) . ?
C6 O5 1.459(2) . ?
C6 C19 1.494(3) . ?
C7 C8 1.527(2) . ?
C8 C9 1.536(2) . ?
C9 C10 1.514(2) . ?
C9 C15 1.592(3) . ?
C10 C22 1.332(2) . ?
C11 C12 1.315(3) . ?
C11 C16 1.442(3) . ?
C12 C13 1.495(3) . ?
C13 C14 1.541(3) . ?
C13 C27 1.541(3) . ?
C13 C28 1.545(3) . ?
C14 C24 1.541(2) . ?
C14 C15 1.567(2) . ?
C15 C16 1.537(3) . ?
C15 C25 1.540(2) . ?
C16 O26 1.222(2) . ?
C17 C18 1.318(3) . ?
C17 O21 1.385(3) . ?
C18 C19 1.403(3) . ?
C19 C20 1.346(3) . ?
C20 O21 1.349(3) . ?
C24 C29 1.501(3) . ?
C29 O30 1.193(2) . ?
C29 O31 1.335(2) . ?
C32 O31 1.448(3) . ?

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
C2 C1 C6 107.57(15) . . ?
C2 C1 C33 107.68(16) . . ?
C6 C1 C33 112.34(16) . . ?
C2 C1 C7 110.13(14) . . ?
C6 C1 C7 107.99(15) . . ?
C33 C1 C7 111.08(17) . . ?
C3 C2 C10 122.69(17) . . ?
C3 C2 C1 119.39(17) . . ?
C10 C2 C1 117.65(16) . . ?
C2 C3 C4 122.52(18) . . ?
O23 C4 O5 117.94(18) . . ?
O23 C4 C3 124.03(19) . . ?
O5 C4 C3 117.92(18) . . ?
O5 C6 C19 105.20(15) . . ?
O5 C6 C1 111.64(14) . . ?
C19 C6 C1 115.71(17) . . ?
C8 C7 C1 113.23(16) . . ?
C7 C8 C9 114.58(16) . . ?
C10 C9 C8 108.96(15) . . ?
C10 C9 C15 112.84(14) . . ?
C8 C9 C15 118.65(16) . . ?
C22 C10 C2 118.82(17) . . ?
C22 C10 C9 122.42(18) . . ?
C2 C10 C9 118.55(16) . . ?
C12 C11 C16 122.0(2) . . ?
C11 C12 C13 124.7(2) . . ?
C12 C13 C14 108.13(16) . . ?
C12 C13 C27 107.74(17) . . ?
C14 C13 C27 108.74(16) . . ?
C12 C13 C28 108.58(18) . . ?
C14 C13 C28 115.25(17) . . ?
C27 C13 C28 108.17(16) . . ?
C24 C14 C13 112.45(15) . . ?
C24 C14 C15 112.80(15) . . ?
C13 C14 C15 117.07(15) . . ?
C16 C15 C25 106.05(16) . . ?
C16 C15 C14 110.44(16) . . ?
C25 C15 C14 113.86(15) . . ?
C16 C15 C9 108.87(14) . . ?
C25 C15 C9 111.46(16) . . ?
C14 C15 C9 106.14(14) . . ?
O26 C16 C11 119.2(2) . . ?
O26 C16 C15 120.8(2) . . ?
C11 C16 C15 119.94(17) . . ?
C18 C17 O21 108.9(2) . . ?
C17 C18 C19 109.1(2) . . ?
C20 C19 C18 104.9(2) . . ?
C20 C19 C6 127.0(2) . . ?
C18 C19 C6 128.05(19) . . ?
C19 C20 O21 111.3(2) . . ?
C29 C24 C14 115.93(17) . . ?
O30 C29 O31 123.6(2) . . ?
O30 C29 C24 126.4(2) . . ?
O31 C29 C24 110.0(2) . . ?
C4 O5 C6 117.29(15) . . ?
C20 O21 C17 105.83(19) . . ?
C29 O31 C32 115.6(2) . . ?