# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2008



data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'J. Stephen Clark'
_publ_contact_author_email       STEPHENC@CHEM.GLA.AC.UK

_publ_section_title              
;
Synthetic Studies on the Cornexistins:
Synthesis of (+-) 5-epi-Hydroxycornexistin
;
_publ_author_name                'J. Stephen Clark'

data_nitnon
_database_code_depnum_ccdc_archive 'CCDC 693627'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H23 N O8'
_chemical_formula_weight         441.42
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   'P 21/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                   7.2351(7)
_cell_length_b                   25.532(2)
_cell_length_c                   12.0626(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.539(2)
_cell_angle_gamma                90.00
_cell_volume                     2156.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7955
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      27.45
_exptl_crystal_description       'hexagonal plate'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?

_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART1000 CCD area detector'
_diffrn_measurement_method       omega
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            18983
_diffrn_reflns_av_R_equivalents  0.067
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         27.46
_reflns_number_total             4848
_reflns_number_gt                3821
_reflns_threshold_expression     >2\s(I)
_computing_data_collection       'Bruker SMART version 5.624 (Bruker, 2001)'
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2000)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'enCIFer (CCDC, 2003); PLATON (Spek, 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 Rfactors
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^)+(0.0731P)^2^+0.2235P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   'CH geometrically placed, OH from delta-F'
_refine_ls_hydrogen_treatment    'riding model, OH as rigid rotor'
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4848
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1205
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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

O1 O 0.09095(13) 0.26772(4) -0.07716(8) 0.0304(2) Uani 1 1 d . . .
N1 N 1.03830(17) 0.03491(5) 0.23048(11) 0.0327(3) Uani 1 1 d . . .
C1 C 0.17212(18) 0.31907(5) -0.04450(11) 0.0252(3) Uani 1 1 d . . .
H1A H 0.1734 0.3395 -0.1150 0.030 Uiso 1 1 calc R . .
O2 O -0.16000(16) 0.22146(5) -0.05545(9) 0.0437(3) Uani 1 1 d . . .
C2 C 0.03317(18) 0.34404(5) 0.01448(11) 0.0260(3) Uani 1 1 d . . .
O3 O 0.49122(15) 0.47403(4) 0.11123(9) 0.0373(3) Uani 1 1 d . . .
C3 C 0.03885(19) 0.40042(5) 0.04977(12) 0.0295(3) Uani 1 1 d . . .
H3A H -0.0299 0.4214 -0.0169 0.035 Uiso 1 1 calc R . .
H3B H -0.0314 0.4041 0.1100 0.035 Uiso 1 1 calc R . .
O4 O 0.67039(13) 0.32996(4) 0.24264(8) 0.0317(2) Uani 1 1 d . . .
H4 H 0.7517 0.3188 0.3003 0.048 Uiso 1 1 calc R . .
C4 C 0.23431(19) 0.42314(5) 0.09385(11) 0.0269(3) Uani 1 1 d . . .
O5 O 0.51153(13) 0.23679(3) 0.14051(8) 0.0276(2) Uani 1 1 d . . .
C5 C 0.37749(18) 0.40668(5) 0.19360(11) 0.0252(3) Uani 1 1 d . . .
O6 O 0.33822(15) 0.18943(4) 0.23541(10) 0.0381(3) Uani 1 1 d . . .
C6 C 0.36541(18) 0.36097(5) 0.27031(11) 0.0245(3) Uani 1 1 d . . .
H6A H 0.2290 0.3495 0.2528 0.029 Uiso 1 1 calc R . .
O7 O 1.16759(17) 0.04168(5) 0.18372(12) 0.0559(4) Uani 1 1 d . . .
C7 C 0.48511(18) 0.31390(5) 0.24859(11) 0.0248(3) Uani 1 1 d . . .
H7A H 0.5008 0.2896 0.3153 0.030 Uiso 1 1 calc R . .
O8 O 1.02447(16) -0.00374(4) 0.28757(11) 0.0462(3) Uani 1 1 d . . .
C8 C 0.39161(18) 0.28296(5) 0.14067(11) 0.0240(3) Uani 1 1 d . . .
H8A H 0.2614 0.2715 0.1448 0.029 Uiso 1 1 calc R . .
C9 C 0.37748(17) 0.31101(5) 0.02639(11) 0.0237(3) Uani 1 1 d . . .
H9A H 0.4406 0.3456 0.0419 0.028 Uiso 1 1 calc R . .
H9B H 0.4477 0.2903 -0.0192 0.028 Uiso 1 1 calc R . .
C10 C -0.09863(19) 0.30889(6) 0.02157(12) 0.0313(3) Uani 1 1 d . . .
H10A H -0.1976 0.3139 0.0595 0.038 Uiso 1 1 calc R . .
C11 C -0.0673(2) 0.26146(6) -0.03797(12) 0.0322(3) Uani 1 1 d . . .
C12 C 0.3102(2) 0.46332(6) 0.04757(12) 0.0335(3) Uani 1 1 d . . .
H12A H 0.2468 0.4816 -0.0198 0.040 Uiso 1 1 calc R . .
C13 C 0.5275(2) 0.43889(5) 0.19951(12) 0.0316(3) Uani 1 1 d . . .
H13A H 0.6436 0.4373 0.2576 0.038 Uiso 1 1 calc R . .
C14 C 0.4261(2) 0.37631(6) 0.39795(12) 0.0347(3) Uani 1 1 d . . .
H14A H 0.4209 0.3447 0.4448 0.042 Uiso 1 1 calc R . .
H14B H 0.5603 0.3885 0.4164 0.042 Uiso 1 1 calc R . .
C15 C 0.3029(2) 0.41910(6) 0.43187(13) 0.0414(4) Uani 1 1 d . . .
H15A H 0.3551 0.4276 0.5138 0.050 Uiso 1 1 calc R . .
H15B H 0.3116 0.4511 0.3871 0.050 Uiso 1 1 calc R . .
C16 C 0.0945(3) 0.40411(8) 0.41279(16) 0.0544(5) Uani 1 1 d . . .
H16A H 0.0242 0.4332 0.4362 0.082 Uiso 1 1 calc R . .
H16B H 0.0841 0.3730 0.4584 0.082 Uiso 1 1 calc R . .
H16C H 0.0406 0.3965 0.3315 0.082 Uiso 1 1 calc R . .
C17 C 0.47451(19) 0.19430(5) 0.19592(11) 0.0256(3) Uani 1 1 d . . .
C18 C 0.62407(18) 0.15313(5) 0.20349(11) 0.0246(3) Uani 1 1 d . . .
C19 C 0.5919(2) 0.10389(5) 0.24439(12) 0.0310(3) Uani 1 1 d . . .
H19A H 0.4774 0.0972 0.2669 0.037 Uiso 1 1 calc R . .
C20 C 0.7268(2) 0.06457(5) 0.25240(13) 0.0319(3) Uani 1 1 d . . .
H20A H 0.7063 0.0307 0.2797 0.038 Uiso 1 1 calc R . .
C21 C 0.89155(19) 0.07603(5) 0.21957(11) 0.0268(3) Uani 1 1 d . . .
C22 C 0.92735(19) 0.12453(5) 0.17860(12) 0.0293(3) Uani 1 1 d . . .
H22A H 1.0421 0.1311 0.1563 0.035 Uiso 1 1 calc R . .
C23 C 0.79125(19) 0.16328(5) 0.17103(11) 0.0280(3) Uani 1 1 d . . .
H23A H 0.8124 0.1970 0.1434 0.034 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 0.0285(5) 0.0351(5) 0.0282(5) -0.0055(4) 0.0082(4) -0.0050(4)
N1 0.0297(6) 0.0288(6) 0.0378(6) 0.0035(5) 0.0053(5) 0.0025(5)
C1 0.0225(6) 0.0294(7) 0.0240(6) 0.0000(5) 0.0068(5) -0.0013(5)
O2 0.0411(6) 0.0498(7) 0.0380(6) -0.0071(5) 0.0058(5) -0.0205(5)
C2 0.0191(6) 0.0366(7) 0.0209(6) 0.0003(5) 0.0023(5) 0.0036(5)
O3 0.0402(6) 0.0321(5) 0.0413(6) 0.0076(5) 0.0133(5) -0.0049(4)
C3 0.0256(7) 0.0346(7) 0.0281(7) 0.0010(6) 0.0066(5) 0.0070(6)
O4 0.0193(5) 0.0391(6) 0.0348(5) 0.0061(4) 0.0034(4) -0.0015(4)
C4 0.0282(7) 0.0271(6) 0.0264(6) 0.0009(5) 0.0087(5) 0.0048(5)
O5 0.0261(5) 0.0253(5) 0.0352(5) 0.0049(4) 0.0150(4) 0.0033(4)
C5 0.0257(6) 0.0256(6) 0.0252(6) -0.0001(5) 0.0081(5) 0.0001(5)
O6 0.0364(6) 0.0338(6) 0.0530(7) 0.0063(5) 0.0275(5) 0.0015(4)
C6 0.0242(6) 0.0269(6) 0.0225(6) 0.0020(5) 0.0061(5) -0.0008(5)
O7 0.0460(7) 0.0508(7) 0.0813(9) 0.0235(7) 0.0353(7) 0.0192(6)
C7 0.0196(6) 0.0288(7) 0.0257(6) 0.0055(5) 0.0051(5) 0.0005(5)
O8 0.0437(7) 0.0306(6) 0.0652(8) 0.0164(5) 0.0155(6) 0.0063(5)
C8 0.0193(6) 0.0257(6) 0.0287(6) 0.0032(5) 0.0091(5) 0.0031(5)
C9 0.0198(6) 0.0278(6) 0.0253(6) 0.0013(5) 0.0093(5) 0.0003(5)
C10 0.0194(6) 0.0467(8) 0.0283(7) -0.0016(6) 0.0067(5) -0.0013(6)
C11 0.0243(7) 0.0443(8) 0.0253(7) -0.0003(6) 0.0010(5) -0.0069(6)
C12 0.0379(8) 0.0310(7) 0.0321(7) 0.0056(6) 0.0097(6) 0.0047(6)
C13 0.0326(7) 0.0300(7) 0.0318(7) 0.0026(6) 0.0072(6) -0.0032(6)
C14 0.0411(8) 0.0368(8) 0.0244(7) 0.0006(6) 0.0049(6) 0.0005(6)
C15 0.0560(10) 0.0414(8) 0.0283(7) -0.0037(6) 0.0135(7) 0.0029(7)
C16 0.0587(11) 0.0634(12) 0.0495(10) -0.0028(9) 0.0294(9) 0.0081(9)
C17 0.0261(6) 0.0257(6) 0.0263(6) -0.0002(5) 0.0088(5) -0.0033(5)
C18 0.0244(6) 0.0256(6) 0.0236(6) 0.0000(5) 0.0057(5) -0.0016(5)
C19 0.0265(7) 0.0295(7) 0.0387(8) 0.0039(6) 0.0114(6) -0.0038(5)
C20 0.0320(7) 0.0238(6) 0.0395(8) 0.0056(6) 0.0081(6) -0.0030(6)
C21 0.0257(6) 0.0256(6) 0.0273(6) 0.0008(5) 0.0034(5) 0.0020(5)
C22 0.0264(7) 0.0312(7) 0.0321(7) 0.0050(6) 0.0103(6) 0.0000(5)
C23 0.0284(7) 0.0251(6) 0.0322(7) 0.0047(5) 0.0108(6) -0.0008(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
O1 C11 1.3536(17) . ?
O1 C1 1.4501(16) . ?
N1 O7 1.2198(16) . ?
N1 O8 1.2217(16) . ?
N1 C21 1.4753(17) . ?
C1 C2 1.5108(18) . ?
C1 C9 1.5308(17) . ?
O2 C11 1.2107(17) . ?
C2 C10 1.3278(19) . ?
C2 C3 1.4987(19) . ?
O3 C13 1.3667(17) . ?
O3 C12 1.3693(18) . ?
C3 C4 1.4972(19) . ?
O4 C7 1.4207(15) . ?
C4 C12 1.349(2) . ?
C4 C5 1.4394(18) . ?
O5 C17 1.3362(15) . ?
O5 C8 1.4640(15) . ?
C5 C13 1.3494(19) . ?
C5 C6 1.5057(18) . ?
O6 C17 1.2044(16) . ?
C6 C7 1.5417(18) . ?
C6 C14 1.5419(18) . ?
C7 C8 1.5277(18) . ?
C8 C9 1.5339(17) . ?
C10 C11 1.454(2) . ?
C14 C15 1.529(2) . ?
C15 C16 1.516(3) . ?
C17 C18 1.4948(18) . ?
C18 C23 1.3861(18) . ?
C18 C19 1.3914(18) . ?
C19 C20 1.3862(19) . ?
C20 C21 1.3785(19) . ?
C21 C22 1.3816(19) . ?
C22 C23 1.3826(19) . ?
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
C11 O1 C1 109.41(10) . . ?
O7 N1 O8 123.77(12) . . ?
O7 N1 C21 118.44(12) . . ?
O8 N1 C21 117.78(12) . . ?
O1 C1 C2 103.73(10) . . ?
O1 C1 C9 107.48(10) . . ?
C2 C1 C9 117.45(10) . . ?
C10 C2 C3 126.86(12) . . ?
C10 C2 C1 108.58(12) . . ?
C3 C2 C1 124.40(12) . . ?
C13 O3 C12 106.00(11) . . ?
C4 C3 C2 115.42(11) . . ?
C12 C4 C5 106.60(12) . . ?
C12 C4 C3 126.45(13) . . ?
C5 C4 C3 126.95(12) . . ?
C17 O5 C8 117.38(10) . . ?
C13 C5 C4 105.48(12) . . ?
C13 C5 C6 127.58(12) . . ?
C4 C5 C6 126.83(12) . . ?
C5 C6 C7 112.21(10) . . ?
C5 C6 C14 111.77(11) . . ?
C7 C6 C14 109.66(11) . . ?
O4 C7 C8 109.13(10) . . ?
O4 C7 C6 111.17(10) . . ?
C8 C7 C6 113.60(10) . . ?
O5 C8 C7 106.36(10) . . ?
O5 C8 C9 106.29(10) . . ?
C7 C8 C9 116.09(11) . . ?
C1 C9 C8 113.65(10) . . ?
C2 C10 C11 109.13(12) . . ?
O2 C11 O1 121.25(14) . . ?
O2 C11 C10 129.82(14) . . ?
O1 C11 C10 108.93(12) . . ?
C4 C12 O3 110.56(12) . . ?
C5 C13 O3 111.35(12) . . ?
C15 C14 C6 114.19(12) . . ?
C16 C15 C14 113.77(14) . . ?
O6 C17 O5 124.64(12) . . ?
O6 C17 C18 123.73(12) . . ?
O5 C17 C18 111.63(11) . . ?
C23 C18 C19 120.30(12) . . ?
C23 C18 C17 121.40(12) . . ?
C19 C18 C17 118.31(12) . . ?
C20 C19 C18 120.10(13) . . ?
C21 C20 C19 118.08(12) . . ?
C20 C21 C22 123.11(13) . . ?
C20 C21 N1 118.57(12) . . ?
C22 C21 N1 118.31(12) . . ?
C21 C22 C23 118.07(12) . . ?
C22 C23 C18 120.34(12) . . ?
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

C11 O1 C1 C2 -3.05(13) . . . . ?
C11 O1 C1 C9 122.01(11) . . . . ?
O1 C1 C2 C10 4.66(14) . . . . ?
C9 C1 C2 C10 -113.72(13) . . . . ?
O1 C1 C2 C3 -171.05(11) . . . . ?
C9 C1 C2 C3 70.57(16) . . . . ?
C10 C2 C3 C4 147.76(13) . . . . ?
C1 C2 C3 C4 -37.33(18) . . . . ?
C2 C3 C4 C12 118.17(15) . . . . ?
C2 C3 C4 C5 -62.05(18) . . . . ?
C12 C4 C5 C13 0.58(15) . . . . ?
C3 C4 C5 C13 -179.23(13) . . . . ?
C12 C4 C5 C6 -175.99(12) . . . . ?
C3 C4 C5 C6 4.2(2) . . . . ?
C13 C5 C6 C7 -72.10(17) . . . . ?
C4 C5 C6 C7 103.74(15) . . . . ?
C13 C5 C6 C14 51.57(18) . . . . ?
C4 C5 C6 C14 -132.59(14) . . . . ?
C5 C6 C7 O4 46.68(14) . . . . ?
C14 C6 C7 O4 -78.17(13) . . . . ?
C5 C6 C7 C8 -76.88(14) . . . . ?
C14 C6 C7 C8 158.28(11) . . . . ?
C17 O5 C8 C7 87.68(12) . . . . ?
C17 O5 C8 C9 -148.03(11) . . . . ?
O4 C7 C8 O5 61.89(12) . . . . ?
C6 C7 C8 O5 -173.45(9) . . . . ?
O4 C7 C8 C9 -56.09(14) . . . . ?
C6 C7 C8 C9 68.57(14) . . . . ?
O1 C1 C9 C8 -65.14(13) . . . . ?
C2 C1 C9 C8 51.22(16) . . . . ?
O5 C8 C9 C1 123.67(11) . . . . ?
C7 C8 C9 C1 -118.31(12) . . . . ?
C3 C2 C10 C11 171.11(12) . . . . ?
C1 C2 C10 C11 -4.46(15) . . . . ?
C1 O1 C11 O2 179.70(12) . . . . ?
C1 O1 C11 C10 0.57(14) . . . . ?
C2 C10 C11 O2 -176.46(15) . . . . ?
C2 C10 C11 O1 2.57(16) . . . . ?
C5 C4 C12 O3 -0.52(16) . . . . ?
C3 C4 C12 O3 179.30(12) . . . . ?
C13 O3 C12 C4 0.25(16) . . . . ?
C4 C5 C13 O3 -0.45(16) . . . . ?
C6 C5 C13 O3 176.10(12) . . . . ?
C12 O3 C13 C5 0.14(16) . . . . ?
C5 C6 C14 C15 60.75(16) . . . . ?
C7 C6 C14 C15 -174.15(12) . . . . ?
C6 C14 C15 C16 61.07(18) . . . . ?
C8 O5 C17 O6 8.16(19) . . . . ?
C8 O5 C17 C18 -171.68(10) . . . . ?
O6 C17 C18 C23 -170.88(13) . . . . ?
O5 C17 C18 C23 8.96(17) . . . . ?
O6 C17 C18 C19 9.0(2) . . . . ?
O5 C17 C18 C19 -171.13(12) . . . . ?
C23 C18 C19 C20 -0.3(2) . . . . ?
C17 C18 C19 C20 179.79(12) . . . . ?
C18 C19 C20 C21 0.4(2) . . . . ?
C19 C20 C21 C22 -0.4(2) . . . . ?
C19 C20 C21 N1 178.47(12) . . . . ?
O7 N1 C21 C20 167.50(14) . . . . ?
O8 N1 C21 C20 -13.57(19) . . . . ?
O7 N1 C21 C22 -13.5(2) . . . . ?
O8 N1 C21 C22 165.39(13) . . . . ?
C20 C21 C22 C23 0.4(2) . . . . ?
N1 C21 C22 C23 -178.54(12) . . . . ?
C21 C22 C23 C18 -0.3(2) . . . . ?
C19 C18 C23 C22 0.2(2) . . . . ?
C17 C18 C23 C22 -179.87(12) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O2 0.84 1.98 2.7678(15) 155.1 4_666
_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.045

data_nofulc
_database_code_depnum_ccdc_archive 'CCDC 693628'
_audit_creation_method           'enCIFer editing of SHELXL97 CIF output'
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 O3'
_chemical_formula_sum            'C16 H18 O3'
_chemical_formula_weight         258.30
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   'P 21/n'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a                   10.3476(7)
_cell_length_b                   12.7195(9)
_cell_length_c                   11.1244(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.035(2)
_cell_angle_gamma                90.00
_cell_volume                     1337.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5260
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.5
_exptl_crystal_description       tablet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  .
_exptl_absorpt_correction_T_max  .
_exptl_absorpt_process_details   .

_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11914
_diffrn_reflns_av_R_equivalents  0.096
_diffrn_reflns_av_sigmaI/netI    0.060
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         27.51
_reflns_number_total             3087
_reflns_number_gt                2629
_reflns_threshold_expression     >2\s(I)
_computing_data_collection       'Bruker SMART version 5.625 (Bruker,2001)'
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker,2000)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'enCIFer(Allen et al.,2004);PLATON(Spek,2003)'
_refine_special_details          
;
;
_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^)+(0.056P)^2^+0.208P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   .
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3087
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0435

_refine_ls_wR_factor_ref         0.122
_refine_ls_wR_factor_gt          0.118
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_restrained_S_all      1.08
_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
O1 O 0.91355(9) 0.25968(6) 0.86767(9) 0.0318(2) Uani 1 1 d . . .
O2 O 1.07350(9) 0.14094(8) 0.98855(9) 0.0377(2) Uani 1 1 d . . .
O3 O 0.36038(10) -0.05814(7) 0.81197(11) 0.0429(3) Uani 1 1 d . . .
C1 C 0.76293(13) 0.26119(9) 0.78437(12) 0.0284(3) Uani 1 1 d . . .
H1A H 0.7469 0.2843 0.6935 0.034 Uiso 1 1 calc R . .
C2 C 0.71783(13) 0.14852(9) 0.78230(11) 0.0259(3) Uani 1 1 d . . .
C3 C 0.57333(12) 0.10908(9) 0.69186(12) 0.0298(3) Uani 1 1 d . . .
H3A H 0.5191 0.1686 0.6371 0.036 Uiso 1 1 calc R . .
H3B H 0.5850 0.0561 0.6319 0.036 Uiso 1 1 calc R . .
C4 C 0.48777(12) 0.06095(9) 0.75893(12) 0.0293(3) Uani 1 1 d . . .
C5 C 0.43424(12) 0.10941(9) 0.84699(12) 0.0278(3) Uani 1 1 d . . .
C6 C 0.46204(12) 0.21974(8) 0.90214(12) 0.0258(2) Uani 1 1 d . . .
H6A H 0.5634 0.2242 0.9659 0.031 Uiso 1 1 calc R . .
C7 C 0.43828(13) 0.29839(9) 0.79313(12) 0.0286(3) Uani 1 1 d . . .
H7A H 0.3427 0.3123 0.7357 0.034 Uiso 1 1 calc R . .
C8 C 0.53657(14) 0.34981(9) 0.76944(13) 0.0316(3) Uani 1 1 d . . .
H8A H 0.5049 0.3978 0.6978 0.038 Uiso 1 1 calc R . .
C9 C 0.69365(14) 0.33927(9) 0.84544(13) 0.0325(3) Uani 1 1 d . . .
H9A H 0.7129 0.3162 0.9361 0.039 Uiso 1 1 calc R . .
H9B H 0.7379 0.4092 0.8513 0.039 Uiso 1 1 calc R . .
C10 C 0.82753(12) 0.09274(9) 0.86358(11) 0.0277(3) Uani 1 1 d . . .
H10A H 0.8252 0.0204 0.8840 0.033 Uiso 1 1 calc R . .
C11 C 0.95240(13) 0.16088(9) 0.91649(11) 0.0289(3) Uani 1 1 d . . .
C12 C 0.44011(14) -0.03911(10) 0.74252(14) 0.0378(3) Uani 1 1 d . . .
H12A H 0.4597 -0.0897 0.6894 0.045 Uiso 1 1 calc R . .
C13 C 0.35832(13) 0.03399(10) 0.87445(14) 0.0363(3) Uani 1 1 d . . .
H13A H 0.3098 0.0437 0.9300 0.044 Uiso 1 1 calc R . .
C14 C 0.36928(14) 0.24703(10) 0.97590(13) 0.0329(3) Uani 1 1 d . . .
H14A H 0.2686 0.2400 0.9145 0.040 Uiso 1 1 calc R . .
H14B H 0.3881 0.1955 1.0478 0.040 Uiso 1 1 calc R . .
C15 C 0.39374(15) 0.35734(10) 1.03416(13) 0.0358(3) Uani 1 1 d . . .
H15A H 0.3753 0.4090 0.9624 0.043 Uiso 1 1 calc R . .
H15B H 0.3252 0.3709 1.0737 0.043 Uiso 1 1 calc R . .
C16 C 0.54201(17) 0.37419(11) 1.13796(14) 0.0440(3) Uani 1 1 d . . .
H16A H 0.5510 0.4462 1.1718 0.066 Uiso 1 1 calc R . .
H16B H 0.6105 0.3629 1.0990 0.066 Uiso 1 1 calc R . .
H16C H 0.5605 0.3243 1.2103 0.066 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 0.0310(5) 0.0333(4) 0.0357(5) 0.0029(3) 0.0183(4) -0.0031(3)
O2 0.0287(5) 0.0514(6) 0.0313(5) 0.0055(4) 0.0104(4) -0.0018(4)
O3 0.0358(5) 0.0310(5) 0.0575(6) -0.0035(4) 0.0145(5) -0.0086(4)
C1 0.0303(6) 0.0307(6) 0.0291(6) 0.0038(5) 0.0170(5) 0.0018(5)
C2 0.0307(6) 0.0284(5) 0.0231(5) -0.0021(4) 0.0154(5) 0.0020(4)
C3 0.0296(6) 0.0324(6) 0.0255(6) -0.0050(5) 0.0092(5) 0.0043(5)
C4 0.0237(5) 0.0285(6) 0.0301(6) -0.0026(4) 0.0051(5) 0.0027(4)
C5 0.0229(5) 0.0281(5) 0.0302(6) 0.0016(4) 0.0085(5) 0.0004(4)
C6 0.0263(5) 0.0253(5) 0.0292(6) 0.0009(4) 0.0147(4) 0.0004(4)
C7 0.0330(6) 0.0272(5) 0.0287(6) 0.0015(4) 0.0158(5) 0.0081(5)
C8 0.0439(7) 0.0245(5) 0.0350(6) 0.0054(5) 0.0250(6) 0.0081(5)
C9 0.0402(7) 0.0245(5) 0.0426(7) -0.0018(5) 0.0270(6) -0.0032(5)
C10 0.0304(6) 0.0289(5) 0.0257(5) 0.0007(4) 0.0136(5) 0.0010(4)
C11 0.0323(6) 0.0351(6) 0.0240(6) 0.0015(4) 0.0164(5) -0.0008(5)
C12 0.0308(6) 0.0322(6) 0.0437(8) -0.0072(5) 0.0084(6) -0.0011(5)
C13 0.0314(6) 0.0324(6) 0.0441(7) 0.0004(5) 0.0144(6) -0.0034(5)
C14 0.0341(6) 0.0372(7) 0.0355(7) 0.0017(5) 0.0224(5) -0.0001(5)
C15 0.0461(8) 0.0369(6) 0.0338(7) 0.0020(5) 0.0258(6) 0.0068(5)
C16 0.0550(9) 0.0414(7) 0.0371(7) -0.0081(6) 0.0203(7) -0.0008(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 C11 1.3631(14) . ?
O1 C1 1.4531(14) . ?
O2 C11 1.2078(15) . ?
O3 C12 1.3621(19) . ?
O3 C13 1.3671(17) . ?
C1 C2 1.5044(16) . ?
C1 C9 1.5357(17) . ?
C1 H1A 1.0000 . ?
C2 C10 1.3316(16) . ?
C2 C3 1.5080(16) . ?
C3 C4 1.5012(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C12 1.3502(17) . ?
C4 C5 1.4451(17) . ?
C5 C13 1.3514(18) . ?
C5 C6 1.5115(15) . ?
C6 C7 1.5129(16) . ?
C6 C14 1.5351(17) . ?
C6 H6A 1.0000 . ?
C7 C8 1.3228(18) . ?
C7 H7A 0.9500 . ?
C8 C9 1.5017(19) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.4655(17) . ?
C10 H10A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C14 C15 1.5229(17) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.513(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
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

C11 O1 C1 109.38(9) . . ?
C12 O3 C13 105.93(10) . . ?
O1 C1 C2 104.04(9) . . ?
O1 C1 C9 107.41(10) . . ?
C2 C1 C9 115.15(10) . . ?
O1 C1 H1A 110.0 . . ?
C2 C1 H1A 110.0 . . ?
C9 C1 H1A 110.0 . . ?
C10 C2 C1 108.89(11) . . ?
C10 C2 C3 127.96(11) . . ?
C1 C2 C3 122.97(10) . . ?
C4 C3 C2 115.42(10) . . ?
C4 C3 H3A 108.4 . . ?
C2 C3 H3A 108.4 . . ?
C4 C3 H3B 108.4 . . ?
C2 C3 H3B 108.4 . . ?
H3A C3 H3B 107.5 . . ?
C12 C4 C5 105.90(12) . . ?
C12 C4 C3 125.03(12) . . ?
C5 C4 C3 129.01(10) . . ?
C13 C5 C4 105.60(11) . . ?
C13 C5 C6 126.83(12) . . ?
C4 C5 C6 127.52(10) . . ?
C5 C6 C7 110.28(10) . . ?
C5 C6 C14 111.70(10) . . ?
C7 C6 C14 110.25(9) . . ?
C5 C6 H6A 108.2 . . ?
C7 C6 H6A 108.2 . . ?
C14 C6 H6A 108.2 . . ?
C8 C7 C6 126.83(11) . . ?
C8 C7 H7A 116.6 . . ?
C6 C7 H7A 116.6 . . ?
C7 C8 C9 125.97(11) . . ?
C7 C8 H8A 117.0 . . ?
C9 C8 H8A 117.0 . . ?
C8 C9 C1 113.70(10) . . ?
C8 C9 H9A 108.8 . . ?
C1 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
C1 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C2 C10 C11 109.02(11) . . ?
C2 C10 H10A 125.5 . . ?
C11 C10 H10A 125.5 . . ?
O2 C11 O1 121.06(11) . . ?
O2 C11 C10 130.47(12) . . ?
O1 C11 C10 108.45(10) . . ?
C4 C12 O3 111.29(12) . . ?
C4 C12 H12A 124.4 . . ?
O3 C12 H12A 124.4 . . ?
C5 C13 O3 111.27(13) . . ?
C5 C13 H13A 124.4 . . ?
O3 C13 H13A 124.4 . . ?
C15 C14 C6 113.84(10) . . ?
C15 C14 H14A 108.8 . . ?
C6 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C6 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C16 C15 C14 113.35(11) . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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

C11 O1 C1 C2 -3.56(12) . . . . ?
C11 O1 C1 C9 118.96(10) . . . . ?
O1 C1 C2 C10 4.67(13) . . . . ?
C9 C1 C2 C10 -112.59(12) . . . . ?
O1 C1 C2 C3 -170.81(10) . . . . ?
C9 C1 C2 C3 71.92(15) . . . . ?
C10 C2 C3 C4 64.50(16) . . . . ?
C1 C2 C3 C4 -120.92(12) . . . . ?
C2 C3 C4 C12 -119.64(13) . . . . ?
C2 C3 C4 C5 63.35(15) . . . . ?
C12 C4 C5 C13 -0.48(13) . . . . ?
C3 C4 C5 C13 176.98(11) . . . . ?
C12 C4 C5 C6 177.08(11) . . . . ?
C3 C4 C5 C6 -5.46(19) . . . . ?
C13 C5 C6 C7 -134.17(13) . . . . ?
C4 C5 C6 C7 48.77(15) . . . . ?
C13 C5 C6 C14 -11.20(16) . . . . ?
C4 C5 C6 C14 171.73(11) . . . . ?
C5 C6 C7 C8 -105.85(14) . . . . ?
C14 C6 C7 C8 130.33(13) . . . . ?
C6 C7 C8 C9 1.0(2) . . . . ?
C7 C8 C9 C1 95.23(15) . . . . ?
O1 C1 C9 C8 179.80(9) . . . . ?
C2 C1 C9 C8 -64.85(14) . . . . ?
C1 C2 C10 C11 -3.99(13) . . . . ?
C3 C2 C10 C11 171.21(11) . . . . ?
C1 O1 C11 O2 179.94(11) . . . . ?
C1 O1 C11 C10 1.37(13) . . . . ?
C2 C10 C11 O2 -176.65(13) . . . . ?
C2 C10 C11 O1 1.74(13) . . . . ?
C5 C4 C12 O3 0.32(14) . . . . ?
C3 C4 C12 O3 -177.26(10) . . . . ?
C13 O3 C12 C4 -0.04(14) . . . . ?
C4 C5 C13 O3 0.47(14) . . . . ?
C6 C5 C13 O3 -177.11(10) . . . . ?
C12 O3 C13 C5 -0.29(14) . . . . ?
C5 C6 C14 C15 179.69(10) . . . . ?
C7 C6 C14 C15 -57.33(14) . . . . ?
C6 C14 C15 C16 -63.05(15) . . . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.19
_refine_diff_density_rms         0.05
#===END of CIF