# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       yzli@chem.ecnu.edu.cn
_publ_contact_author_name        'Yanzhong Li'
_publ_author_name                'Y. Li'

data_mo_dm11253_0m
_database_code_depnum_ccdc_archive 'CCDC 850260'
#TrackingRef 'mo_dm11253_0m.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 O6'
_chemical_formula_weight         382.40

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/c

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

_cell_length_a                   24.115(3)
_cell_length_b                   10.4602(11)
_cell_length_c                   15.5022(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.746(2)
_cell_angle_gamma                90.00
_cell_volume                     3890.7(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    6984
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      29.36

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1616
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9721
_exptl_absorpt_correction_T_max  0.9813
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      133(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 APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13752
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         26.99
_reflns_number_total             4240
_reflns_number_gt                3584
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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^)+(0.0687P)^2^+1.9837P] 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         4240
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.1127
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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 0.04531(4) 0.51044(8) 0.15727(6) 0.0271(2) Uani 1 1 d . . .
O2 O 0.01710(4) 0.89906(9) 0.15098(6) 0.0303(2) Uani 1 1 d . . .
O3 O 0.09826(4) 0.92805(8) 0.23385(6) 0.0238(2) Uani 1 1 d . . .
O4 O 0.30525(4) 0.35573(8) 0.43022(6) 0.0279(2) Uani 1 1 d . . .
O5 O 0.37088(3) 0.55070(9) 0.47454(6) 0.0260(2) Uani 1 1 d . . .
O6 O 0.33834(3) 0.79506(8) 0.43747(6) 0.0268(2) Uani 1 1 d . . .
C1 C -0.05164(5) 0.45399(13) 0.11132(9) 0.0283(3) Uani 1 1 d . . .
H1 H -0.0650 0.5323 0.1323 0.034 Uiso 1 1 calc R . .
C2 C -0.08825(5) 0.36309(13) 0.07293(9) 0.0301(3) Uani 1 1 d . . .
H2 H -0.1271 0.3803 0.0672 0.036 Uiso 1 1 calc R . .
C3 C -0.06932(6) 0.24817(13) 0.04295(9) 0.0286(3) Uani 1 1 d . . .
H3 H -0.0948 0.1874 0.0163 0.034 Uiso 1 1 calc R . .
C4 C -0.01254(6) 0.22268(12) 0.05226(9) 0.0298(3) Uani 1 1 d . . .
H4 H 0.0009 0.1432 0.0331 0.036 Uiso 1 1 calc R . .
C5 C 0.02469(5) 0.31281(12) 0.08946(9) 0.0271(3) Uani 1 1 d . . .
H5 H 0.0636 0.2959 0.0952 0.033 Uiso 1 1 calc R . .
C6 C 0.00476(5) 0.42742(11) 0.11808(8) 0.0226(3) Uani 1 1 d . . .
C7 C 0.03578(5) 0.63693(11) 0.15553(8) 0.0227(3) Uani 1 1 d . . .
H7 H 0.0034 0.6696 0.1230 0.027 Uiso 1 1 calc R . .
C8 C 0.07166(5) 0.71772(11) 0.19935(8) 0.0206(2) Uani 1 1 d . . .
C9 C 0.05861(5) 0.85664(11) 0.19127(8) 0.0217(3) Uani 1 1 d . . .
C10 C 0.08855(6) 1.06508(12) 0.22991(9) 0.0300(3) Uani 1 1 d . . .
H10A H 0.0553 1.0871 0.2595 0.036 Uiso 1 1 calc R . .
H10B H 0.0821 1.0934 0.1688 0.036 Uiso 1 1 calc R . .
C11 C 0.13928(6) 1.12992(13) 0.27410(9) 0.0349(3) Uani 1 1 d . . .
H11A H 0.1428 1.1091 0.3360 0.052 Uiso 1 1 calc R . .
H11B H 0.1356 1.2227 0.2666 0.052 Uiso 1 1 calc R . .
H11C H 0.1725 1.1002 0.2484 0.052 Uiso 1 1 calc R . .
C12 C 0.12076(5) 0.67625(11) 0.25033(8) 0.0206(2) Uani 1 1 d . . .
C13 C 0.16246(5) 0.64455(11) 0.29367(8) 0.0216(3) Uani 1 1 d . . .
C14 C 0.21484(5) 0.61920(11) 0.34305(8) 0.0200(2) Uani 1 1 d . . .
C15 C 0.23271(5) 0.49410(11) 0.36134(8) 0.0210(2) Uani 1 1 d . . .
H15 H 0.2099 0.4237 0.3419 0.025 Uiso 1 1 calc R . .
C16 C 0.28427(5) 0.47351(11) 0.40829(8) 0.0203(2) Uani 1 1 d . . .
C17 C 0.31868(5) 0.57670(11) 0.43562(7) 0.0197(2) Uani 1 1 d . . .
C18 C 0.30065(5) 0.70127(11) 0.41471(8) 0.0200(2) Uani 1 1 d . . .
C19 C 0.24858(5) 0.72273(11) 0.37029(8) 0.0213(2) Uani 1 1 d . . .
H19 H 0.2360 0.8076 0.3585 0.026 Uiso 1 1 calc R . .
C20 C 0.27460(6) 0.24850(12) 0.39458(10) 0.0340(3) Uani 1 1 d . . .
H20A H 0.2380 0.2463 0.4168 0.051 Uiso 1 1 calc R . .
H20B H 0.2949 0.1698 0.4112 0.051 Uiso 1 1 calc R . .
H20C H 0.2698 0.2556 0.3312 0.051 Uiso 1 1 calc R . .
C21 C 0.38564(6) 0.60714(14) 0.55782(9) 0.0319(3) Uani 1 1 d . . .
H21A H 0.3932 0.6984 0.5508 0.048 Uiso 1 1 calc R . .
H21B H 0.4190 0.5650 0.5858 0.048 Uiso 1 1 calc R . .
H21C H 0.3548 0.5966 0.5939 0.048 Uiso 1 1 calc R . .
C22 C 0.32215(6) 0.92318(12) 0.41644(10) 0.0328(3) Uani 1 1 d . . .
H22A H 0.3124 0.9305 0.3537 0.049 Uiso 1 1 calc R . .
H22B H 0.3531 0.9811 0.4344 0.049 Uiso 1 1 calc R . .
H22C H 0.2898 0.9461 0.4468 0.049 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 0.0222(4) 0.0206(4) 0.0359(5) -0.0022(4) -0.0094(4) -0.0012(3)
O2 0.0254(5) 0.0267(5) 0.0361(5) -0.0012(4) -0.0111(4) 0.0063(4)
O3 0.0235(4) 0.0196(4) 0.0270(5) -0.0001(3) -0.0045(3) -0.0009(3)
O4 0.0271(5) 0.0178(4) 0.0373(5) 0.0040(4) -0.0052(4) 0.0044(3)
O5 0.0168(4) 0.0328(5) 0.0267(5) -0.0017(4) -0.0058(3) 0.0056(4)
O6 0.0199(4) 0.0196(4) 0.0393(5) -0.0015(4) -0.0053(4) -0.0030(3)
C1 0.0235(6) 0.0257(6) 0.0353(7) -0.0041(5) 0.0010(5) 0.0004(5)
C2 0.0182(6) 0.0342(7) 0.0370(7) 0.0019(6) -0.0012(5) -0.0040(5)
C3 0.0283(6) 0.0280(6) 0.0281(6) 0.0012(5) -0.0030(5) -0.0104(5)
C4 0.0320(7) 0.0218(6) 0.0351(7) -0.0027(5) 0.0017(6) -0.0019(5)
C5 0.0216(6) 0.0232(6) 0.0357(7) 0.0011(5) -0.0019(5) -0.0004(5)
C6 0.0212(6) 0.0215(6) 0.0239(6) 0.0008(5) -0.0038(5) -0.0044(5)
C7 0.0197(6) 0.0213(6) 0.0258(6) 0.0007(5) -0.0034(4) 0.0017(4)
C8 0.0173(5) 0.0212(6) 0.0223(6) 0.0009(4) -0.0026(4) 0.0018(4)
C9 0.0206(6) 0.0223(6) 0.0215(6) -0.0005(4) -0.0021(4) 0.0010(4)
C10 0.0349(7) 0.0185(6) 0.0360(7) -0.0009(5) 0.0010(6) 0.0004(5)
C11 0.0428(8) 0.0287(7) 0.0341(7) -0.0066(6) 0.0083(6) -0.0117(6)
C12 0.0183(5) 0.0188(5) 0.0241(6) -0.0006(4) -0.0015(4) -0.0012(4)
C13 0.0189(6) 0.0193(5) 0.0260(6) 0.0003(4) -0.0013(5) 0.0000(4)
C14 0.0159(5) 0.0213(6) 0.0221(6) -0.0001(4) -0.0013(4) 0.0011(4)
C15 0.0187(6) 0.0190(5) 0.0246(6) 0.0000(4) -0.0015(4) -0.0018(4)
C16 0.0212(6) 0.0177(5) 0.0219(6) 0.0025(4) 0.0014(4) 0.0032(4)
C17 0.0158(5) 0.0230(6) 0.0195(5) 0.0005(4) -0.0019(4) 0.0029(4)
C18 0.0168(5) 0.0199(6) 0.0229(6) -0.0024(4) 0.0001(4) -0.0012(4)
C19 0.0191(6) 0.0177(5) 0.0263(6) 0.0009(4) -0.0007(5) 0.0031(4)
C20 0.0419(8) 0.0176(6) 0.0410(8) -0.0017(5) -0.0025(6) 0.0035(5)
C21 0.0309(7) 0.0369(7) 0.0254(6) 0.0011(5) -0.0098(5) 0.0009(6)
C22 0.0290(7) 0.0192(6) 0.0492(9) -0.0022(6) -0.0017(6) -0.0030(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 C7 1.3427(15) . ?
O1 C6 1.4001(14) . ?
O2 C9 1.2099(14) . ?
O3 C9 1.3347(14) . ?
O3 C10 1.4528(15) . ?
O4 C16 1.3619(14) . ?
O4 C20 1.4240(16) . ?
O5 C17 1.3676(13) . ?
O5 C21 1.4319(16) . ?
O6 C18 1.3598(14) . ?
O6 C22 1.4245(15) . ?
C1 C6 1.3819(18) . ?
C1 C2 1.3901(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3870(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.3812(18) . ?
C5 H5 0.9500 . ?
C7 C8 1.3441(17) . ?
C7 H7 0.9500 . ?
C8 C12 1.4238(16) . ?
C8 C9 1.4894(16) . ?
C10 C11 1.5027(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.1989(17) . ?
C13 C14 1.4346(16) . ?
C14 C19 1.3944(16) . ?
C14 C15 1.3979(16) . ?
C15 C16 1.3931(16) . ?
C15 H15 0.9500 . ?
C16 C17 1.4008(16) . ?
C17 C18 1.4014(16) . ?
C18 C19 1.3884(16) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C7 O1 C6 119.45(9) . . ?
C9 O3 C10 115.26(10) . . ?
C16 O4 C20 116.77(10) . . ?
C17 O5 C21 116.78(10) . . ?
C18 O6 C22 117.29(9) . . ?
C6 C1 C2 118.23(12) . . ?
C6 C1 H1 120.9 . . ?
C2 C1 H1 120.9 . . ?
C3 C2 C1 121.44(12) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 119.18(12) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 120.21(12) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 119.48(12) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 121.44(11) . . ?
C5 C6 O1 115.30(11) . . ?
C1 C6 O1 123.20(11) . . ?
O1 C7 C8 120.61(11) . . ?
O1 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C12 123.12(11) . . ?
C7 C8 C9 116.81(10) . . ?
C12 C8 C9 120.06(10) . . ?
O2 C9 O3 124.39(11) . . ?
O2 C9 C8 123.93(11) . . ?
O3 C9 C8 111.68(10) . . ?
O3 C10 C11 107.79(11) . . ?
O3 C10 H10A 110.1 . . ?
C11 C10 H10A 110.1 . . ?
O3 C10 H10B 110.1 . . ?
C11 C10 H10B 110.1 . . ?
H10A C10 H10B 108.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C8 178.31(13) . . ?
C12 C13 C14 173.97(13) . . ?
C19 C14 C15 120.46(10) . . ?
C19 C14 C13 118.29(10) . . ?
C15 C14 C13 121.22(10) . . ?
C16 C15 C14 119.45(10) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
O4 C16 C15 124.05(11) . . ?
O4 C16 C17 115.32(10) . . ?
C15 C16 C17 120.63(10) . . ?
O5 C17 C16 118.12(10) . . ?
O5 C17 C18 122.52(10) . . ?
C16 C17 C18 119.06(10) . . ?
O6 C18 C19 124.04(11) . . ?
O6 C18 C17 115.27(10) . . ?
C19 C18 C17 120.62(10) . . ?
C18 C19 C14 119.73(11) . . ?
C18 C19 H19 120.1 . . ?
C14 C19 H19 120.1 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O5 C21 H21A 109.5 . . ?
O5 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O5 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O6 C22 H22A 109.5 . . ?
O6 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O6 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.060