# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Jian Gong'
_publ_contact_author_email       gongjian0618@163.com
_publ_author_name                'Youhong Hu'

data_mo_dm1166_0m
_database_code_depnum_ccdc_archive 'CCDC 814417'
#TrackingRef 'mo_dm1166_0m.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H20 O4'
_chemical_formula_weight         456.47

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.037(4)
_cell_length_b                   12.336(6)
_cell_length_c                   13.346(7)
_cell_angle_alpha                76.670(9)
_cell_angle_beta                 76.633(9)
_cell_angle_gamma                83.431(9)
_cell_volume                     1094.4(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1140
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      27.40

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9909
_exptl_absorpt_correction_T_max  0.9955
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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            6737
_diffrn_reflns_av_R_equivalents  0.0741
_diffrn_reflns_av_sigmaI/netI    0.1398
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3828
_reflns_number_gt                1679
_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^)+(0.1255P)^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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3828
_refine_ls_number_parameters     321
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1658
_refine_ls_R_factor_gt           0.0766
_refine_ls_wR_factor_ref         0.2406
_refine_ls_wR_factor_gt          0.1881
_refine_ls_goodness_of_fit_ref   0.901
_refine_ls_restrained_S_all      0.901
_refine_ls_shift/su_max          0.052
_refine_ls_shift/su_mean         0.001

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 0.0113(7) 0.5539(4) 0.1843(4) 0.0451(13) Uani 1 1 d . . .
C2 C -0.1549(8) 0.5967(4) 0.1440(5) 0.0640(16) Uani 1 1 d . . .
H2 H -0.1720 0.5814 0.0817 0.077 Uiso 1 1 calc R . .
C3 C -0.2934(8) 0.6624(5) 0.1992(5) 0.0664(17) Uani 1 1 d . . .
H3 H -0.4040 0.6931 0.1733 0.080 Uiso 1 1 calc R . .
C4 C -0.2682(9) 0.6825(4) 0.2920(6) 0.0718(18) Uani 1 1 d . . .
H4 H -0.3651 0.7242 0.3299 0.086 Uiso 1 1 calc R . .
C5 C -0.1020(8) 0.6423(4) 0.3302(5) 0.0568(15) Uani 1 1 d . . .
H5 H -0.0851 0.6583 0.3923 0.068 Uiso 1 1 calc R . .
C6 C 0.0407(7) 0.5771(4) 0.2745(4) 0.0439(12) Uani 1 1 d . . .
C7 C 0.2229(7) 0.5352(4) 0.3113(4) 0.0476(13) Uani 1 1 d . . .
C8 C 0.3476(7) 0.4561(3) 0.2543(4) 0.0374(11) Uani 1 1 d . . .
C9 C 0.3013(7) 0.4368(4) 0.1669(4) 0.0428(12) Uani 1 1 d . . .
C10 C 0.4034(7) 0.3580(4) 0.1110(4) 0.0438(13) Uani 1 1 d . . .
H10 H 0.3638 0.3488 0.0518 0.053 Uiso 1 1 calc R . .
C11 C 0.5588(7) 0.2947(4) 0.1409(3) 0.0397(12) Uani 1 1 d . . .
C12 C 0.6261(6) 0.3162(3) 0.2279(3) 0.0328(10) Uani 1 1 d . . .
C13 C 0.5197(6) 0.3941(3) 0.2863(3) 0.0347(11) Uani 1 1 d . . .
C14 C 0.5840(7) 0.4068(4) 0.3749(4) 0.0432(13) Uani 1 1 d . . .
H14 H 0.5133 0.4554 0.4159 0.052 Uiso 1 1 calc R . .
C15 C 0.7481(7) 0.3488(4) 0.4016(4) 0.0421(13) Uani 1 1 d . . .
H15 H 0.7905 0.3609 0.4589 0.051 Uiso 1 1 calc R . .
C16 C 0.8531(6) 0.2724(3) 0.3451(3) 0.0329(11) Uani 1 1 d . . .
C17 C 0.7958(6) 0.2578(3) 0.2576(3) 0.0344(11) Uani 1 1 d . . .
H17 H 0.8696 0.2090 0.2176 0.041 Uiso 1 1 calc R . .
C18 C 0.6428(7) 0.2018(4) 0.0884(3) 0.0366(11) Uani 1 1 d . . .
C19 C 0.6980(8) 0.2169(4) -0.0205(4) 0.0492(14) Uani 1 1 d . . .
H19 H 0.6959 0.2888 -0.0616 0.059 Uiso 1 1 calc R . .
C20 C 0.7549(8) 0.1291(5) -0.0686(4) 0.0527(14) Uani 1 1 d . . .
H20 H 0.7965 0.1426 -0.1415 0.063 Uiso 1 1 calc R . .
C21 C 0.7526(7) 0.0205(4) -0.0119(4) 0.0457(13) Uani 1 1 d . . .
C22 C 0.7024(7) 0.0045(4) 0.0976(4) 0.0457(13) Uani 1 1 d . . .
H22 H 0.7061 -0.0675 0.1385 0.055 Uiso 1 1 calc R . .
C23 C 0.6479(7) 0.0928(4) 0.1456(4) 0.0415(12) Uani 1 1 d . . .
H23 H 0.6133 0.0795 0.2188 0.050 Uiso 1 1 calc R . .
C24 C 0.8059(8) -0.0781(5) -0.0637(4) 0.0611(16) Uani 1 1 d . . .
H24A H 0.7133 -0.1339 -0.0309 0.092 Uiso 1 1 calc R . .
H24B H 0.9347 -0.1087 -0.0561 0.092 Uiso 1 1 calc R . .
H24C H 0.8035 -0.0546 -0.1372 0.092 Uiso 1 1 calc R . .
C25 C 1.0352(7) 0.2123(4) 0.3782(3) 0.0376(11) Uani 1 1 d . . .
C26 C 1.0869(7) 0.0962(4) 0.3729(3) 0.0357(11) Uani 1 1 d . . .
C27 C 1.2710(8) 0.0476(4) 0.3881(4) 0.0481(13) Uani 1 1 d . . .
C28 C 1.3208(9) -0.0626(4) 0.3828(4) 0.0567(15) Uani 1 1 d . . .
H28 H 1.4444 -0.0934 0.3913 0.068 Uiso 1 1 calc R . .
C29 C 1.1946(9) -0.1263(4) 0.3654(4) 0.0567(15) Uani 1 1 d . . .
H29 H 1.2326 -0.1999 0.3601 0.068 Uiso 1 1 calc R . .
C30 C 1.0077(8) -0.0831(4) 0.3553(4) 0.0490(13) Uani 1 1 d . . .
H30 H 0.9191 -0.1278 0.3449 0.059 Uiso 1 1 calc R . .
C31 C 0.9547(7) 0.0260(4) 0.3608(3) 0.0398(12) Uani 1 1 d . . .
H31 H 0.8278 0.0542 0.3563 0.048 Uiso 1 1 calc R . .
O1 O 0.2595(6) 0.5665(3) 0.3846(3) 0.0822(15) Uani 1 1 d . . .
O2 O 0.1412(5) 0.4883(3) 0.1275(3) 0.0534(10) Uani 1 1 d . . .
O3 O 1.1333(5) 0.2647(3) 0.4125(3) 0.0520(10) Uani 1 1 d . . .
O4 O 1.4016(5) 0.1061(3) 0.4069(3) 0.0596(11) Uani 1 1 d . . .
H1 H 1.313(8) 0.175(5) 0.431(4) 0.080(18) Uiso 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 0.044(3) 0.034(3) 0.060(3) -0.009(3) -0.022(3) 0.005(2)
C2 0.062(4) 0.057(3) 0.076(4) -0.010(3) -0.034(3) 0.013(3)
C3 0.044(3) 0.057(4) 0.109(5) -0.018(4) -0.043(4) 0.006(3)
C4 0.053(4) 0.052(3) 0.117(6) -0.030(4) -0.029(4) 0.017(3)
C5 0.052(3) 0.043(3) 0.083(4) -0.024(3) -0.025(3) 0.007(3)
C6 0.042(3) 0.030(3) 0.063(3) -0.012(3) -0.019(3) 0.004(2)
C7 0.047(3) 0.047(3) 0.060(3) -0.023(3) -0.024(3) 0.002(2)
C8 0.038(3) 0.033(3) 0.044(3) -0.010(2) -0.013(2) -0.002(2)
C9 0.043(3) 0.043(3) 0.047(3) -0.010(2) -0.023(3) 0.008(2)
C10 0.047(3) 0.054(3) 0.038(3) -0.016(2) -0.025(2) 0.007(3)
C11 0.043(3) 0.044(3) 0.033(3) -0.008(2) -0.012(2) 0.002(2)
C12 0.033(3) 0.031(2) 0.036(3) -0.002(2) -0.013(2) -0.005(2)
C13 0.035(3) 0.031(2) 0.042(3) -0.010(2) -0.014(2) -0.002(2)
C14 0.049(3) 0.043(3) 0.047(3) -0.022(2) -0.020(3) 0.006(2)
C15 0.052(3) 0.042(3) 0.040(3) -0.012(2) -0.025(3) 0.003(2)
C16 0.034(3) 0.032(2) 0.037(3) -0.010(2) -0.015(2) 0.000(2)
C17 0.038(3) 0.031(2) 0.037(3) -0.010(2) -0.012(2) -0.001(2)
C18 0.038(3) 0.044(3) 0.034(3) -0.014(2) -0.015(2) 0.000(2)
C19 0.060(3) 0.053(3) 0.034(3) -0.010(3) -0.012(3) 0.005(3)
C20 0.058(4) 0.070(4) 0.035(3) -0.021(3) -0.012(3) 0.004(3)
C21 0.030(3) 0.066(4) 0.053(3) -0.033(3) -0.013(2) 0.002(2)
C22 0.049(3) 0.042(3) 0.048(3) -0.013(2) -0.012(3) 0.003(2)
C23 0.045(3) 0.047(3) 0.036(3) -0.014(2) -0.009(2) -0.003(2)
C24 0.046(3) 0.081(4) 0.072(4) -0.044(3) -0.018(3) 0.005(3)
C25 0.039(3) 0.048(3) 0.028(2) -0.010(2) -0.011(2) -0.001(2)
C26 0.037(3) 0.044(3) 0.030(2) -0.011(2) -0.016(2) 0.006(2)
C27 0.049(3) 0.059(3) 0.035(3) -0.010(3) -0.011(2) 0.006(3)
C28 0.064(4) 0.050(3) 0.051(3) -0.011(3) -0.013(3) 0.021(3)
C29 0.084(4) 0.036(3) 0.044(3) -0.007(3) -0.009(3) 0.012(3)
C30 0.065(4) 0.042(3) 0.047(3) -0.010(2) -0.023(3) -0.004(3)
C31 0.041(3) 0.047(3) 0.037(3) -0.008(2) -0.020(2) -0.002(2)
O1 0.076(3) 0.100(3) 0.101(3) -0.071(3) -0.051(3) 0.043(2)
O2 0.052(2) 0.061(2) 0.054(2) -0.0165(19) -0.0328(19) 0.0189(18)
O3 0.054(2) 0.053(2) 0.059(2) -0.0145(18) -0.0300(19) -0.0011(18)
O4 0.044(2) 0.065(3) 0.074(3) -0.012(2) -0.026(2) 0.003(2)

_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 O2 1.363(5) . ?
C1 C6 1.365(7) . ?
C1 C2 1.398(7) . ?
C2 C3 1.383(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.474(6) . ?
C7 O1 1.220(5) . ?
C7 C8 1.462(6) . ?
C8 C9 1.358(6) . ?
C8 C13 1.452(6) . ?
C9 O2 1.380(5) . ?
C9 C10 1.395(6) . ?
C10 C11 1.352(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.438(6) . ?
C11 C18 1.476(6) . ?
C12 C17 1.411(6) . ?
C12 C13 1.414(6) . ?
C13 C14 1.406(6) . ?
C14 C15 1.362(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.374(6) . ?
C16 C25 1.511(6) . ?
C17 H17 0.9300 . ?
C18 C23 1.386(6) . ?
C18 C19 1.389(6) . ?
C19 C20 1.359(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.377(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.394(7) . ?
C21 C24 1.504(6) . ?
C22 C23 1.362(6) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 O3 1.220(5) . ?
C25 C26 1.451(6) . ?
C26 C31 1.400(6) . ?
C26 C27 1.402(6) . ?
C27 O4 1.331(6) . ?
C27 C28 1.379(7) . ?
C28 C29 1.341(8) . ?
C28 H28 0.9300 . ?
C29 C30 1.386(7) . ?
C29 H29 0.9300 . ?
C30 C31 1.370(6) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
O4 H1 1.06(5) . ?

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
O2 C1 C6 122.6(4) . . ?
O2 C1 C2 115.7(4) . . ?
C6 C1 C2 121.7(5) . . ?
C3 C2 C1 118.3(5) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C4 C3 C2 120.2(5) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 121.3(5) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 119.1(5) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C5 119.2(5) . . ?
C1 C6 C7 120.0(4) . . ?
C5 C6 C7 120.8(4) . . ?
O1 C7 C8 124.9(4) . . ?
O1 C7 C6 119.9(4) . . ?
C8 C7 C6 115.2(4) . . ?
C9 C8 C13 116.9(4) . . ?
C9 C8 C7 119.2(4) . . ?
C13 C8 C7 123.9(4) . . ?
C8 C9 O2 123.6(4) . . ?
C8 C9 C10 123.6(4) . . ?
O2 C9 C10 112.7(4) . . ?
C11 C10 C9 121.4(4) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 118.2(4) . . ?
C10 C11 C18 118.9(4) . . ?
C12 C11 C18 122.8(4) . . ?
C17 C12 C13 119.4(4) . . ?
C17 C12 C11 120.4(4) . . ?
C13 C12 C11 120.2(4) . . ?
C14 C13 C12 118.1(4) . . ?
C14 C13 C8 122.5(4) . . ?
C12 C13 C8 119.4(4) . . ?
C15 C14 C13 121.0(4) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 121.3(4) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C17 C16 C15 119.5(4) . . ?
C17 C16 C25 121.9(4) . . ?
C15 C16 C25 118.4(4) . . ?
C16 C17 C12 120.6(4) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C23 C18 C19 116.7(4) . . ?
C23 C18 C11 120.8(4) . . ?
C19 C18 C11 122.1(4) . . ?
C20 C19 C18 121.6(5) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C21 121.6(5) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C20 C21 C22 117.1(4) . . ?
C20 C21 C24 122.6(5) . . ?
C22 C21 C24 120.3(5) . . ?
C23 C22 C21 121.0(5) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C18 121.8(5) . . ?
C22 C23 H23 119.1 . . ?
C18 C23 H23 119.1 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O3 C25 C26 121.6(4) . . ?
O3 C25 C16 117.1(4) . . ?
C26 C25 C16 121.3(4) . . ?
C31 C26 C27 117.1(4) . . ?
C31 C26 C25 122.7(4) . . ?
C27 C26 C25 120.0(4) . . ?
O4 C27 C28 118.5(5) . . ?
O4 C27 C26 121.3(5) . . ?
C28 C27 C26 120.1(5) . . ?
C29 C28 C27 121.3(5) . . ?
C29 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
C28 C29 C30 120.3(5) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C31 C30 C29 119.3(5) . . ?
C31 C30 H30 120.3 . . ?
C29 C30 H30 120.3 . . ?
C30 C31 C26 121.6(4) . . ?
C30 C31 H31 119.2 . . ?
C26 C31 H31 119.2 . . ?
C1 O2 C9 118.6(4) . . ?
C27 O4 H1 102(3) . . ?

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 H1 O3 1.06(5) 1.61(5) 2.560(5) 146(5) .

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.092