# 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_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       jlzhangscience@hotmail.com
_publ_contact_author_name        'Junliang Zhang'
loop_
_publ_author_name
'Junliang Zhang '
'Tao Wang'

data_z
_database_code_depnum_ccdc_archive 'CCDC 796889'
#TrackingRef '4m.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H14 O4'
_chemical_formula_weight         306.30

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   P2(1)/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                   8.3038(3)
_cell_length_b                   10.7343(4)
_cell_length_c                   17.4027(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.7280(10)
_cell_angle_gamma                90.00
_cell_volume                     1543.45(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.36
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9587
_exptl_absorpt_correction_T_max  0.9674
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17451
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0145
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2712
_reflns_number_gt                2347
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0463P)^2^+0.4088P] 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         2712
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0974
_refine_ls_wR_factor_gt          0.0917
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.30654(11) 0.60168(9) 0.07590(5) 0.0445(3) Uani 1 1 d . . .
O2 O 0.39266(19) 0.80257(12) 0.23333(7) 0.0794(4) Uani 1 1 d . . .
O3 O 0.06682(13) 0.97421(10) 0.07709(8) 0.0654(3) Uani 1 1 d . . .
O4 O 0.06728(12) 0.79079(10) -0.05523(6) 0.0474(3) Uani 1 1 d . . .
H4B H 0.027(2) 0.863(2) -0.0429(11) 0.082(6) Uiso 1 1 d . . .
C1 C 0.50170(19) 0.98332(15) 0.10289(9) 0.0552(4) Uani 1 1 d . . .
H1A H 0.5226 0.9027 0.0870 0.066 Uiso 1 1 calc R . .
C2 C 0.6280(2) 1.06496(18) 0.11955(11) 0.0665(5) Uani 1 1 d . . .
H2A H 0.7336 1.0394 0.1150 0.080 Uiso 1 1 calc R . .
C3 C 0.5984(2) 1.18368(17) 0.14285(10) 0.0659(5) Uani 1 1 d . . .
H3A H 0.6839 1.2390 0.1537 0.079 Uiso 1 1 calc R . .
C4 C 0.4422(2) 1.22147(15) 0.15026(9) 0.0633(5) Uani 1 1 d . . .
H4A H 0.4227 1.3020 0.1667 0.076 Uiso 1 1 calc R . .
C5 C 0.3141(2) 1.14041(13) 0.13342(9) 0.0527(4) Uani 1 1 d . . .
H5A H 0.2088 1.1666 0.1381 0.063 Uiso 1 1 calc R . .
C6 C 0.34333(18) 1.01990(13) 0.10954(8) 0.0439(3) Uani 1 1 d . . .
C7 C 0.20570(17) 0.93535(13) 0.08828(8) 0.0442(3) Uani 1 1 d . . .
C8 C 0.23200(16) 0.80176(12) 0.07213(8) 0.0409(3) Uani 1 1 d . . .
C9 C 0.16211(15) 0.74109(12) 0.00449(7) 0.0389(3) Uani 1 1 d . . .
C10 C 0.21227(16) 0.61969(12) 0.00746(8) 0.0398(3) Uani 1 1 d . . .
C11 C 0.31734(17) 0.71197(12) 0.11468(8) 0.0440(3) Uani 1 1 d . . .
C12 C 0.3986(2) 0.71059(15) 0.19309(9) 0.0546(4) Uani 1 1 d . . .
C13 C 0.4825(2) 0.59315(18) 0.22070(11) 0.0745(5) Uani 1 1 d . . .
H13A H 0.5305 0.6044 0.2727 0.112 Uiso 1 1 calc R . .
H13B H 0.5654 0.5735 0.1879 0.112 Uiso 1 1 calc R . .
H13C H 0.4055 0.5263 0.2191 0.112 Uiso 1 1 calc R . .
C14 C 0.18400(16) 0.51363(12) -0.04365(8) 0.0407(3) Uani 1 1 d . . .
C15 C 0.09110(18) 0.52628(14) -0.11453(8) 0.0497(4) Uani 1 1 d . . .
H15A H 0.0490 0.6037 -0.1298 0.060 Uiso 1 1 calc R . .
C16 C 0.0614(2) 0.42445(16) -0.16209(10) 0.0597(4) Uani 1 1 d . . .
H16A H 0.0003 0.4339 -0.2095 0.072 Uiso 1 1 calc R . .
C17 C 0.1211(2) 0.30938(16) -0.14022(10) 0.0640(5) Uani 1 1 d . . .
H17A H 0.0999 0.2410 -0.1724 0.077 Uiso 1 1 calc R . .
C18 C 0.2120(2) 0.29572(15) -0.07070(11) 0.0631(5) Uani 1 1 d . . .
H18A H 0.2519 0.2175 -0.0557 0.076 Uiso 1 1 calc R . .
C19 C 0.24530(19) 0.39694(14) -0.02260(9) 0.0523(4) Uani 1 1 d . . .
H19A H 0.3090 0.3868 0.0240 0.063 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 0.0507(6) 0.0354(5) 0.0449(5) 0.0005(4) -0.0072(4) 0.0031(4)
O2 0.1274(12) 0.0566(8) 0.0495(7) -0.0046(6) -0.0150(7) -0.0147(7)
O3 0.0527(7) 0.0431(6) 0.0967(9) -0.0115(6) -0.0112(6) 0.0079(5)
O4 0.0524(6) 0.0386(6) 0.0484(6) -0.0004(4) -0.0095(4) 0.0092(5)
C1 0.0571(9) 0.0480(9) 0.0611(10) -0.0029(7) 0.0096(7) -0.0047(7)
C2 0.0596(10) 0.0672(11) 0.0733(12) 0.0013(9) 0.0099(8) -0.0153(8)
C3 0.0733(12) 0.0629(11) 0.0591(10) 0.0080(8) -0.0055(8) -0.0266(9)
C4 0.0931(13) 0.0363(8) 0.0557(10) 0.0007(7) -0.0156(9) -0.0091(8)
C5 0.0658(10) 0.0384(8) 0.0505(8) -0.0004(6) -0.0109(7) 0.0031(7)
C6 0.0552(8) 0.0355(7) 0.0393(7) 0.0018(6) -0.0026(6) -0.0020(6)
C7 0.0499(8) 0.0378(7) 0.0435(8) -0.0008(6) -0.0022(6) 0.0035(6)
C8 0.0416(7) 0.0354(7) 0.0447(7) -0.0019(6) -0.0002(6) -0.0013(5)
C9 0.0381(7) 0.0359(7) 0.0417(7) 0.0012(6) -0.0010(5) 0.0011(5)
C10 0.0410(7) 0.0370(7) 0.0402(7) 0.0010(6) -0.0016(6) 0.0009(5)
C11 0.0492(8) 0.0357(7) 0.0455(8) -0.0021(6) -0.0037(6) -0.0018(6)
C12 0.0640(10) 0.0498(9) 0.0473(9) 0.0039(7) -0.0089(7) -0.0112(7)
C13 0.0823(13) 0.0737(12) 0.0619(11) 0.0124(9) -0.0208(9) 0.0075(10)
C14 0.0427(7) 0.0358(7) 0.0440(7) -0.0019(6) 0.0058(6) 0.0002(5)
C15 0.0579(9) 0.0426(8) 0.0475(8) -0.0029(6) -0.0004(7) 0.0008(7)
C16 0.0710(11) 0.0582(10) 0.0488(9) -0.0120(8) 0.0008(8) -0.0056(8)
C17 0.0819(12) 0.0497(10) 0.0617(11) -0.0201(8) 0.0138(9) -0.0080(8)
C18 0.0785(11) 0.0369(8) 0.0758(12) -0.0049(8) 0.0168(9) 0.0078(8)
C19 0.0622(9) 0.0414(8) 0.0527(9) 0.0001(7) 0.0029(7) 0.0085(7)

_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 1.3613(16) . ?
O1 C10 1.3720(16) . ?
O2 C12 1.2142(19) . ?
O3 C7 1.2236(17) . ?
O4 C9 1.3496(16) . ?
O4 H4B 0.88(2) . ?
C1 C2 1.375(2) . ?
C1 C6 1.388(2) . ?
C1 H1A 0.9300 . ?
C2 C3 1.367(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.378(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.383(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.387(2) . ?
C5 H5A 0.9300 . ?
C6 C7 1.477(2) . ?
C7 C8 1.4817(19) . ?
C8 C11 1.3692(19) . ?
C8 C9 1.4179(19) . ?
C9 C10 1.3675(19) . ?
C10 C14 1.4494(19) . ?
C11 C12 1.461(2) . ?
C12 C13 1.496(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C19 1.387(2) . ?
C14 C15 1.395(2) . ?
C15 C16 1.378(2) . ?
C15 H15A 0.9300 . ?
C16 C17 1.371(2) . ?
C16 H16A 0.9300 . ?
C17 C18 1.368(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.382(2) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?

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 C10 108.15(10) . . ?
C9 O4 H4B 111.6(13) . . ?
C2 C1 C6 120.73(16) . . ?
C2 C1 H1A 119.6 . . ?
C6 C1 H1A 119.6 . . ?
C3 C2 C1 120.04(17) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C2 C3 C4 120.07(16) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C3 C4 C5 120.42(16) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C4 C5 C6 119.77(16) . . ?
C4 C5 H5A 120.1 . . ?
C6 C5 H5A 120.1 . . ?
C5 C6 C1 118.95(14) . . ?
C5 C6 C7 119.59(14) . . ?
C1 C6 C7 121.39(13) . . ?
O3 C7 C6 121.58(13) . . ?
O3 C7 C8 117.01(13) . . ?
C6 C7 C8 121.14(12) . . ?
C11 C8 C9 105.82(12) . . ?
C11 C8 C7 131.06(13) . . ?
C9 C8 C7 123.10(12) . . ?
O4 C9 C10 123.91(12) . . ?
O4 C9 C8 128.09(12) . . ?
C10 C9 C8 107.96(12) . . ?
C9 C10 O1 108.20(11) . . ?
C9 C10 C14 134.05(13) . . ?
O1 C10 C14 117.74(11) . . ?
O1 C11 C8 109.83(12) . . ?
O1 C11 C12 117.11(12) . . ?
C8 C11 C12 132.70(13) . . ?
O2 C12 C11 119.27(15) . . ?
O2 C12 C13 122.98(15) . . ?
C11 C12 C13 117.74(14) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 118.52(13) . . ?
C19 C14 C10 120.96(13) . . ?
C15 C14 C10 120.51(12) . . ?
C16 C15 C14 120.26(15) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C17 C16 C15 120.65(16) . . ?
C17 C16 H16A 119.7 . . ?
C15 C16 H16A 119.7 . . ?
C18 C17 C16 119.63(15) . . ?
C18 C17 H17A 120.2 . . ?
C16 C17 H17A 120.2 . . ?
C17 C18 C19 120.68(15) . . ?
C17 C18 H18A 119.7 . . ?
C19 C18 H18A 119.7 . . ?
C18 C19 C14 120.25(15) . . ?
C18 C19 H19A 119.9 . . ?
C14 C19 H19A 119.9 . . ?

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
C6 C1 C2 C3 -0.1(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
C4 C5 C6 C7 -177.29(14) . . . . ?
C2 C1 C6 C5 -0.1(2) . . . . ?
C2 C1 C6 C7 177.02(14) . . . . ?
C5 C6 C7 O3 13.9(2) . . . . ?
C1 C6 C7 O3 -163.15(15) . . . . ?
C5 C6 C7 C8 -172.15(13) . . . . ?
C1 C6 C7 C8 10.8(2) . . . . ?
O3 C7 C8 C11 -132.80(17) . . . . ?
C6 C7 C8 C11 53.0(2) . . . . ?
O3 C7 C8 C9 45.3(2) . . . . ?
C6 C7 C8 C9 -128.88(14) . . . . ?
C11 C8 C9 O4 -179.89(13) . . . . ?
C7 C8 C9 O4 1.6(2) . . . . ?
C11 C8 C9 C10 -2.19(15) . . . . ?
C7 C8 C9 C10 179.28(13) . . . . ?
O4 C9 C10 O1 179.85(12) . . . . ?
C8 C9 C10 O1 2.03(15) . . . . ?
O4 C9 C10 C14 -1.5(2) . . . . ?
C8 C9 C10 C14 -179.35(14) . . . . ?
C11 O1 C10 C9 -1.08(15) . . . . ?
C11 O1 C10 C14 -179.96(12) . . . . ?
C10 O1 C11 C8 -0.34(16) . . . . ?
C10 O1 C11 C12 173.68(12) . . . . ?
C9 C8 C11 O1 1.55(16) . . . . ?
C7 C8 C11 O1 179.92(14) . . . . ?
C9 C8 C11 C12 -171.20(15) . . . . ?
C7 C8 C11 C12 7.2(3) . . . . ?
O1 C11 C12 O2 -170.48(15) . . . . ?
C8 C11 C12 O2 1.9(3) . . . . ?
O1 C11 C12 C13 8.0(2) . . . . ?
C8 C11 C12 C13 -179.64(16) . . . . ?
C9 C10 C14 C19 -176.14(15) . . . . ?
O1 C10 C14 C19 2.4(2) . . . . ?
C9 C10 C14 C15 2.4(2) . . . . ?
O1 C10 C14 C15 -179.11(12) . . . . ?
C19 C14 C15 C16 0.1(2) . . . . ?
C10 C14 C15 C16 -178.46(14) . . . . ?
C14 C15 C16 C17 0.7(3) . . . . ?
C15 C16 C17 C18 -0.5(3) . . . . ?
C16 C17 C18 C19 -0.5(3) . . . . ?
C17 C18 C19 C14 1.3(3) . . . . ?
C15 C14 C19 C18 -1.0(2) . . . . ?
C10 C14 C19 C18 177.50(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.028