# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Pei-Qiang, Huang'
_publ_contact_author_email       pqhuang@xmu.edu.cn

_publ_section_title              
;
The first enantioselective synthesis of cytotoxic marine
natural product palau\^aimide and assignment of its C-20
stereochemistry
;
loop_
_publ_author_name
'Hong-Qiao Lan'
'Yuan-Ping Ruan'
'Huang Pei-Qiang'

# Attachment '- a.cif'

data_a
_database_code_depnum_ccdc_archive 'CCDC 756363'
#TrackingRef '- a.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H25 N O4'
_chemical_formula_sum            'C22 H25 N O4'
_chemical_formula_weight         367.43

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_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1) '

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

_cell_length_a                   11.079(3)
_cell_length_b                   6.5096(15)
_cell_length_c                   13.174(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.774(4)
_cell_angle_gamma                90.00
_cell_volume                     936.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    4979
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      28.65

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   'SADABS - V2.03'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      273(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 AXS area-detector diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5938
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0679
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3125
_reflns_number_gt                2894
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.1124P)^2^+1.4790P] 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   -1(4)
_refine_ls_number_reflns         3125
_refine_ls_number_parameters     244
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.1115
_refine_ls_wR_factor_ref         0.2793
_refine_ls_wR_factor_gt          0.2765
_refine_ls_goodness_of_fit_ref   1.229
_refine_ls_restrained_S_all      1.229
_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
C17 C -0.6824(5) 0.3864(10) 0.2751(4) 0.0347(14) Uani 1 1 d . . .
O2 O -0.3019(4) 0.4322(7) 0.0929(3) 0.0476(12) Uani 1 1 d . . .
N1 N -0.4825(5) 0.2329(8) 0.2637(3) 0.0339(11) Uani 1 1 d . . .
O3 O -0.5140(6) -0.0368(10) 0.4287(4) 0.0760(18) Uani 1 1 d . . .
H3AA H -0.5404 -0.1364 0.4561 0.114 Uiso 1 1 calc R . .
C22 C -0.7209(5) 0.5621(12) 0.3115(5) 0.0435(16) Uani 1 1 d . . .
H5AA H -0.6775 0.6176 0.3718 0.052 Uiso 1 1 calc R . .
O1 O -0.5200(5) -0.0987(8) 0.2197(4) 0.0570(13) Uani 1 1 d . . .
C2 C -0.4741(5) 0.0650(9) 0.2078(4) 0.0324(13) Uani 1 1 d . . .
C4 C -0.3686(5) 0.3066(9) 0.1419(4) 0.0336(14) Uani 1 1 d . . .
C6 C -0.3173(6) 0.4923(10) 0.3097(5) 0.0414(15) Uani 1 1 d . . .
H9AA H -0.2816 0.6097 0.2804 0.050 Uiso 1 1 calc R . .
H9BA H -0.3542 0.5411 0.3668 0.050 Uiso 1 1 calc R . .
C15 C -0.5697(6) 0.2754(10) 0.3306(5) 0.0437(16) Uani 1 1 d . . .
H10A H -0.5296 0.3674 0.3849 0.052 Uiso 1 1 calc R . .
C18 C -0.7494(6) 0.3048(11) 0.1869(5) 0.0448(16) Uani 1 1 d . . .
H11A H -0.7248 0.1819 0.1607 0.054 Uiso 1 1 calc R . .
C19 C -0.8519(6) 0.4030(12) 0.1374(5) 0.0463(16) Uani 1 1 d . . .
H12A H -0.8964 0.3460 0.0778 0.056 Uiso 1 1 calc R . .
C12 C -0.2358(7) 0.2001(16) 0.4187(5) 0.063(2) Uani 1 1 d . . .
H13A H -0.3101 0.1931 0.4425 0.076 Uiso 1 1 calc R . .
O4 O -0.9899(4) 0.6646(9) 0.1190(4) 0.0611(15) Uani 1 1 d . . .
C5 C -0.4189(5) 0.3981(9) 0.2265(4) 0.0352(13) Uani 1 1 d . . .
H15A H -0.4775 0.5057 0.1994 0.042 Uiso 1 1 calc R . .
C21 C -0.8234(6) 0.6625(10) 0.2615(6) 0.0485(18) Uani 1 1 d . . .
H16A H -0.8477 0.7858 0.2875 0.058 Uiso 1 1 calc R . .
C20 C -0.8893(6) 0.5806(12) 0.1738(5) 0.0444(16) Uani 1 1 d . . .
C14 C -0.3813(7) -0.0540(13) 0.0556(6) 0.0557(19) Uani 1 1 d . . .
H18A H -0.3321 -0.0024 0.0079 0.084 Uiso 1 1 calc R . .
H18B H -0.4591 -0.0987 0.0186 0.084 Uiso 1 1 calc R . .
H18C H -0.3402 -0.1678 0.0930 0.084 Uiso 1 1 calc R . .
C7 C -0.2180(6) 0.3435(11) 0.3492(5) 0.0434(16) Uani 1 1 d . . .
C8 C -0.1087(6) 0.3525(11) 0.3150(5) 0.0486(17) Uani 1 1 d . . .
H20A H -0.0971 0.4509 0.2664 0.058 Uiso 1 1 calc R . .
C3 C -0.4006(5) 0.1111(9) 0.1289(4) 0.0328(13) Uani 1 1 d . . .
C9 C -0.0166(7) 0.2203(14) 0.3505(6) 0.057(2) Uani 1 1 d . . .
H22A H 0.0578 0.2295 0.3271 0.069 Uiso 1 1 calc R . .
C13 C -0.2406(7) 0.3543(14) 0.0172(6) 0.060(2) Uani 1 1 d . . .
H23A H -0.1975 0.4634 -0.0102 0.090 Uiso 1 1 calc R . .
H23B H -0.2987 0.2945 -0.0371 0.090 Uiso 1 1 calc R . .
H23C H -0.1833 0.2511 0.0467 0.090 Uiso 1 1 calc R . .
C10 C -0.0332(7) 0.0756(17) 0.4199(6) 0.068(2) Uani 1 1 d . . .
H24A H 0.0294 -0.0159 0.4444 0.082 Uiso 1 1 calc R . .
C16 C -0.6121(7) 0.0872(14) 0.3834(6) 0.062(2) Uani 1 1 d . . .
H25A H -0.6579 0.1314 0.4361 0.074 Uiso 1 1 calc R . .
H25B H -0.6666 0.0068 0.3332 0.074 Uiso 1 1 calc R . .
C23 C -1.0311(9) 0.8460(18) 0.1546(9) 0.088(3) Uani 1 1 d . . .
H26A H -1.1028 0.8909 0.1085 0.132 Uiso 1 1 calc R . .
H26B H -0.9683 0.9486 0.1579 0.132 Uiso 1 1 calc R . .
H26C H -1.0508 0.8250 0.2220 0.132 Uiso 1 1 calc R . .
C11 C -0.1434(8) 0.0642(16) 0.4541(6) 0.073(3) Uani 1 1 d . . .
H27A H -0.1555 -0.0362 0.5016 0.088 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
C17 0.036(3) 0.042(4) 0.029(3) -0.008(3) 0.016(2) -0.012(3)
O2 0.050(3) 0.047(3) 0.048(2) 0.008(2) 0.014(2) 0.002(2)
N1 0.036(3) 0.035(3) 0.029(2) 0.007(2) 0.002(2) 0.006(2)
O3 0.080(4) 0.083(4) 0.061(3) 0.037(3) 0.002(3) 0.002(3)
C22 0.031(3) 0.060(4) 0.039(3) -0.010(3) 0.004(3) -0.003(3)
O1 0.059(3) 0.046(3) 0.069(3) -0.006(3) 0.018(3) -0.007(3)
C2 0.029(3) 0.024(3) 0.039(3) 0.007(2) -0.010(2) -0.006(2)
C4 0.024(3) 0.033(3) 0.037(3) 0.016(3) -0.012(2) 0.014(2)
C6 0.041(4) 0.043(3) 0.039(3) -0.006(3) 0.002(3) -0.007(3)
C15 0.044(4) 0.052(4) 0.032(3) -0.002(3) -0.004(3) 0.000(3)
C18 0.051(4) 0.047(4) 0.039(3) -0.010(3) 0.015(3) 0.003(3)
C19 0.033(3) 0.071(5) 0.033(3) -0.006(3) 0.000(3) -0.003(3)
C12 0.040(4) 0.108(6) 0.041(4) 0.017(4) 0.004(3) -0.006(4)
O4 0.040(3) 0.068(4) 0.069(3) 0.006(3) -0.008(2) 0.017(3)
C5 0.040(3) 0.031(3) 0.034(3) 0.004(3) 0.005(2) 0.015(3)
C21 0.038(3) 0.038(4) 0.073(5) -0.026(3) 0.018(3) -0.003(3)
C20 0.038(3) 0.055(4) 0.044(3) 0.002(3) 0.016(3) -0.007(3)
C14 0.043(4) 0.066(5) 0.055(4) -0.023(4) 0.000(3) -0.018(4)
C7 0.039(3) 0.057(4) 0.030(3) -0.016(3) -0.005(3) -0.012(3)
C8 0.047(4) 0.052(4) 0.045(3) 0.007(3) 0.003(3) -0.012(3)
C3 0.033(3) 0.035(3) 0.025(3) 0.007(2) -0.012(2) 0.011(3)
C9 0.041(4) 0.084(5) 0.047(4) -0.001(4) 0.007(3) 0.000(4)
C13 0.062(5) 0.073(6) 0.049(4) 0.005(4) 0.023(4) 0.003(4)
C10 0.041(4) 0.100(7) 0.058(4) 0.006(5) -0.008(3) 0.017(5)
C16 0.062(5) 0.081(6) 0.045(4) 0.018(4) 0.015(3) 0.002(5)
C23 0.054(5) 0.093(7) 0.107(7) 0.004(6) -0.012(5) 0.026(5)
C11 0.066(5) 0.098(7) 0.053(4) 0.044(5) 0.002(4) 0.013(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
C17 C22 1.338(9) . ?
C17 C18 1.374(9) . ?
C17 C15 1.519(9) . ?
O2 C4 1.338(7) . ?
O2 C13 1.395(8) . ?
N1 C2 1.330(8) . ?
N1 C5 1.418(8) . ?
N1 C15 1.441(8) . ?
O3 C16 1.403(10) . ?
C22 C21 1.376(10) . ?
O1 C2 1.202(7) . ?
C2 C3 1.456(8) . ?
C4 C3 1.325(9) . ?
C4 C5 1.456(8) . ?
C6 C7 1.492(10) . ?
C6 C5 1.557(8) . ?
C15 C16 1.521(10) . ?
C18 C19 1.369(9) . ?
C19 C20 1.344(10) . ?
C12 C7 1.344(10) . ?
C12 C11 1.374(12) . ?
O4 C20 1.338(9) . ?
O4 C23 1.376(12) . ?
C21 C20 1.366(10) . ?
C14 C3 1.485(9) . ?
C7 C8 1.363(9) . ?
C8 C9 1.356(11) . ?
C9 C10 1.347(12) . ?
C10 C11 1.373(11) . ?

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
C22 C17 C18 118.3(6) . . ?
C22 C17 C15 121.4(5) . . ?
C18 C17 C15 120.3(6) . . ?
C4 O2 C13 119.9(5) . . ?
C2 N1 C5 110.3(4) . . ?
C2 N1 C15 127.8(5) . . ?
C5 N1 C15 119.3(5) . . ?
C17 C22 C21 121.5(6) . . ?
O1 C2 N1 125.9(6) . . ?
O1 C2 C3 125.1(6) . . ?
N1 C2 C3 109.0(5) . . ?
C3 C4 O2 133.0(6) . . ?
C3 C4 C5 111.3(6) . . ?
O2 C4 C5 115.7(5) . . ?
C7 C6 C5 113.1(5) . . ?
N1 C15 C17 112.2(5) . . ?
N1 C15 C16 114.6(6) . . ?
C17 C15 C16 108.1(5) . . ?
C19 C18 C17 120.5(6) . . ?
C20 C19 C18 120.8(6) . . ?
C7 C12 C11 119.4(7) . . ?
C20 O4 C23 117.4(7) . . ?
N1 C5 C4 103.4(5) . . ?
N1 C5 C6 113.4(5) . . ?
C4 C5 C6 112.0(5) . . ?
C20 C21 C22 119.9(6) . . ?
O4 C20 C19 116.0(6) . . ?
O4 C20 C21 125.0(7) . . ?
C19 C20 C21 119.0(7) . . ?
C12 C7 C8 119.8(7) . . ?
C12 C7 C6 120.3(6) . . ?
C8 C7 C6 120.0(6) . . ?
C9 C8 C7 121.1(7) . . ?
C4 C3 C2 106.0(5) . . ?
C4 C3 C14 135.6(6) . . ?
C2 C3 C14 118.3(5) . . ?
C10 C9 C8 119.8(7) . . ?
C9 C10 C11 119.5(8) . . ?
O3 C16 C15 112.4(6) . . ?
C10 C11 C12 120.4(8) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.888
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.077