# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_cd212150 _database_code_depnum_ccdc_archive 'CCDC 876688' #TrackingRef 'web_deposit_cif_file_0_Mu-Wang,Chen_1334709633.cd212150.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H16 O3' _chemical_formula_weight 268.30 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 9.7194(11) _cell_length_b 8.3104(10) _cell_length_c 17.6639(19) _cell_angle_alpha 90.00 _cell_angle_beta 97.935(2) _cell_angle_gamma 90.00 _cell_volume 1413.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2152 _cell_measurement_theta_min 4.657 _cell_measurement_theta_max 49.800 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.321 _exptl_crystal_size_mid 0.257 _exptl_crystal_size_min 0.176 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.59954 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _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 8256 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2771 _reflns_number_gt 1966 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0695P)^2^+0.3241P] 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 2771 _refine_ls_number_parameters 201 _refine_ls_number_restraints 40 _refine_ls_R_factor_all 0.0711 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.1509 _refine_ls_wR_factor_gt 0.1346 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.042 _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 0.51059(13) 0.5945(2) 0.08084(7) 0.0739(5) Uani 1 1 d . A . O2 O 0.41870(15) 0.8102(3) -0.02815(10) 0.1082(7) Uani 1 1 d . . . O3 O 0.61920(15) 0.8013(3) -0.07416(9) 0.0931(6) Uani 1 1 d D . . C1 C 0.55282(18) 0.6242(3) 0.15671(10) 0.0592(5) Uani 1 1 d . . . C2 C 0.48436(19) 0.5680(3) 0.21428(12) 0.0729(6) Uani 1 1 d . . . H2 H 0.4039 0.5066 0.2040 0.087 Uiso 1 1 calc R . . C3 C 0.5404(2) 0.6067(3) 0.28814(12) 0.0784(7) Uani 1 1 d . . . H3 H 0.4971 0.5705 0.3287 0.094 Uiso 1 1 calc R . . C4 C 0.6589(2) 0.6978(3) 0.30266(11) 0.0766(6) Uani 1 1 d . . . H4 H 0.6955 0.7212 0.3529 0.092 Uiso 1 1 calc R . . C5 C 0.7246(2) 0.7549(3) 0.24360(11) 0.0656(6) Uani 1 1 d . . . H5 H 0.8041 0.8179 0.2537 0.079 Uiso 1 1 calc R . . C6 C 0.67076(17) 0.7172(2) 0.16949(10) 0.0523(4) Uani 1 1 d . . . C7 C 0.71829(16) 0.7594(2) 0.09446(10) 0.0521(4) Uani 1 1 d . A . H7 H 0.7041 0.8748 0.0848 0.063 Uiso 1 1 calc R . . C8 C 0.61124(17) 0.6625(3) 0.03785(10) 0.0600(5) Uani 1 1 d . . . H8 H 0.6596 0.5756 0.0149 0.072 Uiso 1 1 calc R A . C9 C 0.53561(19) 0.7654(3) -0.02452(11) 0.0723(6) Uani 1 1 d . A . C10 C 0.5658(10) 0.9409(11) -0.1273(4) 0.081(2) Uani 0.50 1 d PDU A 1 H10A H 0.4735 0.9191 -0.1538 0.097 Uiso 0.50 1 calc PR A 1 H10B H 0.5645 1.0413 -0.0993 0.097 Uiso 0.50 1 calc PR A 1 C11 C 0.6709(11) 0.9447(13) -0.1811(5) 0.114(3) Uani 0.55 1 d PDU A 1 H11A H 0.7584 0.9806 -0.1545 0.171 Uiso 0.55 1 calc PR A 1 H11B H 0.6407 1.0173 -0.2224 0.171 Uiso 0.55 1 calc PR A 1 H11C H 0.6814 0.8387 -0.2012 0.171 Uiso 0.55 1 calc PR A 1 C10' C 0.5691(13) 0.8767(13) -0.1451(6) 0.109(3) Uani 0.50 1 d PDU A 2 H10C H 0.4758 0.9171 -0.1440 0.131 Uiso 0.50 1 calc PR A 2 H10D H 0.5663 0.7994 -0.1864 0.131 Uiso 0.50 1 calc PR A 2 C11' C 0.6609(14) 1.0078(12) -0.1573(7) 0.107(3) Uani 0.45 1 d PDU A 2 H11D H 0.6669 1.0808 -0.1149 0.160 Uiso 0.45 1 calc PR A 2 H11E H 0.6252 1.0635 -0.2034 0.160 Uiso 0.45 1 calc PR A 2 H11F H 0.7516 0.9661 -0.1617 0.160 Uiso 0.45 1 calc PR A 2 C12 C 0.86736(17) 0.7165(2) 0.08675(10) 0.0540(5) Uani 1 1 d . . . C13 C 0.9382(2) 0.8024(3) 0.03816(13) 0.0790(7) Uani 1 1 d . A . H13 H 0.8953 0.8889 0.0110 0.095 Uiso 1 1 calc R . . C14 C 1.0727(3) 0.7615(4) 0.02923(15) 0.0982(9) Uani 1 1 d . . . H14 H 1.1194 0.8206 -0.0040 0.118 Uiso 1 1 calc R A . C15 C 1.1375(2) 0.6364(4) 0.06825(15) 0.0912(9) Uani 1 1 d . A . H15 H 1.2289 0.6108 0.0629 0.109 Uiso 1 1 calc R . . C16 C 1.0676(2) 0.5489(4) 0.11513(15) 0.0962(8) Uani 1 1 d . . . H16 H 1.1105 0.4611 0.1412 0.115 Uiso 1 1 calc R A . C17 C 0.9325(2) 0.5890(3) 0.12473(13) 0.0791(7) Uani 1 1 d . A . H17 H 0.8860 0.5282 0.1574 0.095 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 0.0521(7) 0.1092(12) 0.0576(8) -0.0042(8) -0.0027(6) -0.0227(7) O2 0.0521(9) 0.183(2) 0.0867(11) 0.0269(12) -0.0003(8) 0.0258(10) O3 0.0572(8) 0.1534(17) 0.0669(9) 0.0271(10) 0.0028(7) 0.0035(9) C1 0.0425(9) 0.0779(13) 0.0555(10) -0.0012(9) 0.0010(8) 0.0043(9) C2 0.0452(10) 0.0977(17) 0.0758(13) 0.0096(12) 0.0080(9) -0.0008(10) C3 0.0605(12) 0.1123(19) 0.0647(13) 0.0112(12) 0.0164(10) 0.0108(12) C4 0.0715(14) 0.1067(18) 0.0510(11) -0.0072(11) 0.0060(10) 0.0071(13) C5 0.0565(11) 0.0820(15) 0.0563(11) -0.0114(10) 0.0010(9) -0.0008(10) C6 0.0393(8) 0.0637(11) 0.0529(10) -0.0042(8) 0.0029(7) 0.0047(8) C7 0.0420(9) 0.0612(11) 0.0511(9) -0.0028(8) -0.0007(7) 0.0002(8) C8 0.0412(9) 0.0847(14) 0.0520(10) -0.0069(10) -0.0010(7) -0.0022(9) C9 0.0450(10) 0.1155(19) 0.0540(11) -0.0013(11) -0.0014(8) -0.0015(11) C10 0.064(3) 0.126(6) 0.050(3) 0.018(4) -0.001(3) 0.020(4) C11 0.103(4) 0.164(8) 0.080(5) 0.016(5) 0.028(3) -0.006(6) C10' 0.098(4) 0.141(8) 0.081(6) 0.021(5) -0.012(4) -0.014(5) C11' 0.108(6) 0.096(6) 0.110(8) 0.015(5) -0.005(6) -0.001(5) C12 0.0402(9) 0.0695(12) 0.0510(9) -0.0103(9) 0.0020(7) -0.0070(8) C13 0.0646(13) 0.0999(18) 0.0746(14) 0.0050(13) 0.0169(11) -0.0056(12) C14 0.0659(15) 0.145(3) 0.0900(18) -0.0132(18) 0.0329(13) -0.0202(16) C15 0.0436(11) 0.145(3) 0.0858(16) -0.0373(17) 0.0110(11) 0.0011(14) C16 0.0568(13) 0.126(2) 0.1032(19) 0.0007(17) 0.0033(13) 0.0271(14) C17 0.0529(11) 0.0979(18) 0.0872(15) 0.0127(13) 0.0125(10) 0.0113(11) _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 C1 1.369(2) . ? O1 C8 1.435(2) . ? O2 C9 1.189(2) . ? O3 C9 1.309(2) . ? O3 C10' 1.425(10) . ? O3 C10 1.537(9) . ? C1 C2 1.372(3) . ? C1 C6 1.375(3) . ? C2 C3 1.381(3) . ? C2 H2 0.9300 . ? C3 C4 1.373(3) . ? C3 H3 0.9300 . ? C4 C5 1.380(3) . ? C4 H4 0.9300 . ? C5 C6 1.377(2) . ? C5 H5 0.9300 . ? C6 C7 1.504(2) . ? C7 C12 1.516(2) . ? C7 C8 1.563(2) . ? C7 H7 0.9800 . ? C8 C9 1.503(3) . ? C8 H8 0.9800 . ? C10 C11 1.489(11) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C10' C11' 1.442(14) . ? C10' H10C 0.9700 . ? C10' H10D 0.9700 . ? C11' H11D 0.9600 . ? C11' H11E 0.9600 . ? C11' H11F 0.9600 . ? C12 C17 1.363(3) . ? C12 C13 1.373(3) . ? C13 C14 1.381(3) . ? C13 H13 0.9300 . ? C14 C15 1.354(4) . ? C14 H14 0.9300 . ? C15 C16 1.353(4) . ? C15 H15 0.9300 . ? C16 C17 1.387(3) . ? C16 H16 0.9300 . ? C17 H17 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 C1 O1 C8 108.23(13) . . ? C9 O3 C10' 121.4(5) . . ? C9 O3 C10 113.1(4) . . ? C10' O3 C10 23.9(5) . . ? O1 C1 C2 123.62(17) . . ? O1 C1 C6 113.12(16) . . ? C2 C1 C6 123.26(18) . . ? C1 C2 C3 116.9(2) . . ? C1 C2 H2 121.5 . . ? C3 C2 H2 121.5 . . ? C4 C3 C2 121.1(2) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 120.81(19) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C5 C4 119.04(19) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C1 C6 C5 118.86(17) . . ? C1 C6 C7 109.69(15) . . ? C5 C6 C7 131.45(17) . . ? C6 C7 C12 115.96(15) . . ? C6 C7 C8 100.68(14) . . ? C12 C7 C8 112.41(15) . . ? C6 C7 H7 109.1 . . ? C12 C7 H7 109.1 . . ? C8 C7 H7 109.1 . . ? O1 C8 C9 108.16(14) . . ? O1 C8 C7 107.86(14) . . ? C9 C8 C7 113.01(18) . . ? O1 C8 H8 109.2 . . ? C9 C8 H8 109.2 . . ? C7 C8 H8 109.2 . . ? O2 C9 O3 124.7(2) . . ? O2 C9 C8 125.8(2) . . ? O3 C9 C8 109.54(16) . . ? C11 C10 O3 101.7(7) . . ? C11 C10 H10A 111.4 . . ? O3 C10 H10A 111.4 . . ? C11 C10 H10B 111.4 . . ? O3 C10 H10B 111.4 . . ? H10A C10 H10B 109.3 . . ? O3 C10' C11' 108.7(9) . . ? O3 C10' H10C 110.0 . . ? C11' C10' H10C 110.0 . . ? O3 C10' H10D 110.0 . . ? C11' C10' H10D 110.0 . . ? H10C C10' H10D 108.3 . . ? C10' C11' H11D 109.5 . . ? C10' C11' H11E 109.5 . . ? H11D C11' H11E 109.5 . . ? C10' C11' H11F 109.5 . . ? H11D C11' H11F 109.5 . . ? H11E C11' H11F 109.5 . . ? C17 C12 C13 118.24(19) . . ? C17 C12 C7 121.58(18) . . ? C13 C12 C7 120.12(19) . . ? C12 C13 C14 120.5(3) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C15 C14 C13 120.8(2) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C16 C15 C14 119.1(2) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C15 C16 C17 120.6(3) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C12 C17 C16 120.7(2) . . ? C12 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? 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 C8 O1 C1 C2 -176.3(2) . . . . ? C8 O1 C1 C6 4.0(2) . . . . ? O1 C1 C2 C3 179.38(19) . . . . ? C6 C1 C2 C3 -1.0(3) . . . . ? C1 C2 C3 C4 0.2(4) . . . . ? C2 C3 C4 C5 0.8(4) . . . . ? C3 C4 C5 C6 -1.0(3) . . . . ? O1 C1 C6 C5 -179.55(18) . . . . ? C2 C1 C6 C5 0.8(3) . . . . ? O1 C1 C6 C7 0.2(2) . . . . ? C2 C1 C6 C7 -179.45(19) . . . . ? C4 C5 C6 C1 0.2(3) . . . . ? C4 C5 C6 C7 -179.5(2) . . . . ? C1 C6 C7 C12 -125.43(18) . . . . ? C5 C6 C7 C12 54.3(3) . . . . ? C1 C6 C7 C8 -3.88(19) . . . . ? C5 C6 C7 C8 175.8(2) . . . . ? C1 O1 C8 C9 -128.96(18) . . . . ? C1 O1 C8 C7 -6.4(2) . . . . ? C6 C7 C8 O1 6.14(19) . . . . ? C12 C7 C8 O1 130.16(17) . . . . ? C6 C7 C8 C9 125.66(16) . . . . ? C12 C7 C8 C9 -110.32(18) . . . . ? C10' O3 C9 O2 -10.9(6) . . . . ? C10 O3 C9 O2 14.4(5) . . . . ? C10' O3 C9 C8 170.3(5) . . . . ? C10 O3 C9 C8 -164.4(4) . . . . ? O1 C8 C9 O2 14.5(3) . . . . ? C7 C8 C9 O2 -104.9(3) . . . . ? O1 C8 C9 O3 -166.69(18) . . . . ? C7 C8 C9 O3 74.0(2) . . . . ? C9 O3 C10 C11 -174.7(5) . . . . ? C10' O3 C10 C11 -58.9(18) . . . . ? C9 O3 C10' C11' 133.7(8) . . . . ? C10 O3 C10' C11' 57.7(16) . . . . ? C6 C7 C12 C17 29.6(3) . . . . ? C8 C7 C12 C17 -85.5(2) . . . . ? C6 C7 C12 C13 -153.24(19) . . . . ? C8 C7 C12 C13 91.7(2) . . . . ? C17 C12 C13 C14 -1.0(3) . . . . ? C7 C12 C13 C14 -178.3(2) . . . . ? C12 C13 C14 C15 -0.2(4) . . . . ? C13 C14 C15 C16 1.5(4) . . . . ? C14 C15 C16 C17 -1.6(4) . . . . ? C13 C12 C17 C16 0.9(3) . . . . ? C7 C12 C17 C16 178.1(2) . . . . ? C15 C16 C17 C12 0.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.293 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.034