# Electronic Supplementary Material (ESI) for Organic and 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 'Xiaoming Feng' _publ_contact_author_email xmfeng@scu.edu.cn loop_ _publ_author_name 'Qi Zhang' 'Xiao Xiao' 'Lili Lin' 'Xiaohua Liu' 'Xiaoming Feng' data_20101012_s3_zq _database_code_depnum_ccdc_archive 'CCDC 808488' #TrackingRef '20101012_s3_zq.cif' _audit_creation_date ; 'Tue Oct 12 11:22:44 2010' ; _audit_creation_method ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C19 H14 Cl2 O3' _chemical_formula_sum 'C19 H14 Cl2 O3' _chemical_formula_weight 361.20 _chemical_absolute_configuration ad _chemical_melting_point ? _chemical_oxdiff_formula C50H40O8Cl6 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_H-M_alt 'P 1 21 1' _space_group_name_Hall 'P 2yb' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z' _cell_length_a 8.1115(3) _cell_length_b 5.6573(2) _cell_length_c 18.0697(7) _cell_angle_alpha 90.00 _cell_angle_beta 92.887(3) _cell_angle_gamma 90.00 _cell_volume 828.15(6) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2610 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 29.0231 _cell_measurement_theta_min 3.2872 _exptl_absorpt_coefficient_mu 0.406 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.92959 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 372 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.30 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_unetI/netI 0.0490 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 4126 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 29.0231 _diffrn_reflns_theta_min 3.2872 _diffrn_ambient_temperature 120.0 _diffrn_detector_area_resol_mean 16.0874 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -78.00 -52.00 1.0000 4.5000 omega____ theta____ kappa____ phi______ frames - -17.0486 131.0000 108.0000 26 #__ type_ start__ end____ width___ exp.time_ 2 omega -2.00 90.00 1.0000 4.5000 omega____ theta____ kappa____ phi______ frames - 20.0174 38.0000 -60.0000 92 #__ type_ start__ end____ width___ exp.time_ 3 omega 6.00 91.00 1.0000 4.5000 omega____ theta____ kappa____ phi______ frames - 20.0174 38.0000 -150.0000 85 #__ type_ start__ end____ width___ exp.time_ 4 omega -90.00 -55.00 1.0000 4.5000 omega____ theta____ kappa____ phi______ frames - -17.0486 0.0000 -60.0000 35 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0820147000 _diffrn_orient_matrix_UB_12 0.0088002000 _diffrn_orient_matrix_UB_13 0.0115909000 _diffrn_orient_matrix_UB_21 -0.0300715000 _diffrn_orient_matrix_UB_22 -0.0006499000 _diffrn_orient_matrix_UB_23 -0.0375371000 _diffrn_orient_matrix_UB_31 -0.0056305000 _diffrn_orient_matrix_UB_32 -0.1251075000 _diffrn_orient_matrix_UB_33 0.0010187000 _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2484 _reflns_number_total 2764 _reflns_odcompleteness_completeness 99.57 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.184 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.042 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(5) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.914 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 217 _refine_ls_number_reflns 2764 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0318 _refine_ls_R_factor_gt 0.0273 _refine_ls_restrained_S_all 0.914 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0349P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0591 _refine_ls_wR_factor_ref 0.0602 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 Cl1 Cl -0.32270(6) -1.03111(9) 0.01891(3) 0.02450(13) Uani 1 1 d . . . Cl2 Cl -0.12752(6) -0.58289(9) -0.03670(3) 0.02880(14) Uani 1 1 d . . . O1 O -0.90524(15) -1.0755(3) -0.28947(7) 0.0205(3) Uani 1 1 d . . . O2 O -1.14804(19) -1.2643(3) -0.28238(9) 0.0286(4) Uani 1 1 d . . . O3 O -0.67210(19) -1.4952(2) -0.33424(8) 0.0267(4) Uani 1 1 d . . . C1 C -0.3539(2) -0.9263(4) -0.07115(11) 0.0163(4) Uani 1 1 d . . . C2 C -0.2719(2) -0.7275(4) -0.09451(12) 0.0184(5) Uani 1 1 d . . . C3 C -0.3019(3) -0.6441(4) -0.16597(12) 0.0210(5) Uani 1 1 d . . . H3 H -0.2466 -0.5068 -0.1821 0.025 Uiso 1 1 calc R . . C4 C -0.4125(3) -0.7614(4) -0.21381(12) 0.0194(5) Uani 1 1 d . . . H4 H -0.4338 -0.7019 -0.2625 0.023 Uiso 1 1 calc R . . C5 C -0.4933(2) -0.9654(3) -0.19183(11) 0.0169(5) Uani 1 1 d . . . C6 C -0.4626(2) -1.0455(4) -0.11969(10) 0.0173(4) Uani 1 1 d . . . H6 H -0.5167 -1.1837 -0.1035 0.021 Uiso 1 1 calc R . . C7 C -0.6186(2) -1.0911(4) -0.24267(10) 0.0165(4) Uani 1 1 d . . . H7 H -0.6310 -1.2565 -0.2243 0.020 Uiso 1 1 calc R . . C8 C -0.7852(2) -0.9652(4) -0.23839(11) 0.0192(5) Uani 1 1 d . . . H8 H -0.7728 -0.7947 -0.2515 0.023 Uiso 1 1 calc R . . C9 C -0.8618(2) -0.9858(4) -0.16502(12) 0.0222(5) Uani 1 1 d . . . H9 H -0.8160 -0.9240 -0.1196 0.027 Uiso 1 1 calc R . . C10 C -1.0027(2) -1.1030(4) -0.17285(12) 0.0227(5) Uani 1 1 d . . . H10 H -1.0724 -1.1428 -0.1340 0.027 Uiso 1 1 calc R . . C11 C -1.0336(3) -1.1615(4) -0.25149(12) 0.0217(5) Uani 1 1 d . . . C12 C -0.5686(2) -1.1021(4) -0.32351(11) 0.0195(4) Uani 1 1 d . . . H12A H -0.5988 -0.9515 -0.3486 0.023 Uiso 1 1 calc R . . H12B H -0.4474 -1.1210 -0.3244 0.023 Uiso 1 1 calc R . . C13 C -0.6529(3) -1.3067(4) -0.36552(12) 0.0182(5) Uani 1 1 d . . . C14 C -0.7064(2) -1.2779(4) -0.44500(11) 0.0172(4) Uani 1 1 d . . . C15 C -0.8038(3) -1.4551(4) -0.47825(12) 0.0212(5) Uani 1 1 d . . . H15 H -0.8325 -1.5895 -0.4501 0.025 Uiso 1 1 calc R . . C16 C -0.8594(3) -1.4377(4) -0.55194(13) 0.0273(5) Uani 1 1 d . . . H16 H -0.9263 -1.5588 -0.5741 0.033 Uiso 1 1 calc R . . C17 C -0.8163(3) -1.2418(4) -0.59295(13) 0.0272(5) Uani 1 1 d . . . H17 H -0.8539 -1.2288 -0.6434 0.033 Uiso 1 1 calc R . . C18 C -0.7189(3) -1.0652(4) -0.56072(11) 0.0259(5) Uani 1 1 d . . . H18 H -0.6903 -0.9312 -0.5891 0.031 Uiso 1 1 calc R . . C19 C -0.6628(2) -1.0835(4) -0.48687(11) 0.0213(4) Uani 1 1 d . . . H19 H -0.5946 -0.9632 -0.4651 0.026 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 Cl1 0.0298(3) 0.0283(3) 0.0151(2) 0.0019(2) -0.00280(19) 0.0037(2) Cl2 0.0303(3) 0.0301(3) 0.0250(3) -0.0051(3) -0.0087(2) -0.0061(3) O1 0.0172(7) 0.0277(8) 0.0162(7) 0.0034(7) -0.0022(5) -0.0039(7) O2 0.0215(9) 0.0363(9) 0.0277(9) -0.0016(8) -0.0027(7) -0.0107(8) O3 0.0361(9) 0.0206(8) 0.0229(8) 0.0046(7) -0.0046(6) -0.0032(7) C1 0.0170(11) 0.0189(10) 0.0130(11) 0.0010(9) 0.0003(8) 0.0040(9) C2 0.0153(11) 0.0193(11) 0.0201(12) -0.0066(9) -0.0033(8) 0.0025(9) C3 0.0213(11) 0.0191(11) 0.0224(12) 0.0011(9) 0.0010(9) -0.0030(9) C4 0.0222(11) 0.0191(11) 0.0168(11) 0.0025(9) -0.0005(9) 0.0020(9) C5 0.0149(10) 0.0201(11) 0.0159(11) -0.0018(9) 0.0012(8) 0.0000(9) C6 0.0171(9) 0.0162(11) 0.0188(10) 0.0035(10) 0.0022(7) 0.0006(9) C7 0.0179(10) 0.0170(10) 0.0144(10) 0.0005(9) 0.0000(7) -0.0038(9) C8 0.0188(11) 0.0192(11) 0.0193(11) -0.0013(9) -0.0018(8) -0.0035(9) C9 0.0231(11) 0.0256(12) 0.0178(11) -0.0049(10) 0.0012(8) 0.0009(10) C10 0.0196(10) 0.0271(12) 0.0218(11) -0.0020(10) 0.0044(8) -0.0009(10) C11 0.0183(12) 0.0215(11) 0.0253(13) 0.0051(10) 0.0024(9) 0.0022(9) C12 0.0194(10) 0.0228(11) 0.0161(10) 0.0001(10) -0.0003(8) -0.0034(10) C13 0.0160(11) 0.0175(11) 0.0213(12) 0.0004(9) 0.0022(8) -0.0012(9) C14 0.0168(11) 0.0183(10) 0.0168(11) -0.0017(9) 0.0020(8) 0.0032(9) C15 0.0247(12) 0.0181(11) 0.0209(11) -0.0005(10) 0.0004(9) -0.0028(9) C16 0.0275(13) 0.0292(12) 0.0247(13) -0.0040(11) -0.0020(10) -0.0048(11) C17 0.0301(13) 0.0357(14) 0.0154(12) -0.0013(11) -0.0034(9) 0.0035(11) C18 0.0328(12) 0.0249(12) 0.0201(11) 0.0055(11) 0.0033(9) -0.0009(12) C19 0.0223(10) 0.0203(11) 0.0215(10) -0.0007(11) 0.0012(8) -0.0028(10) _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 Cl1 C1 1.738(2) . ? Cl2 C2 1.735(2) . ? O1 C8 1.448(2) . ? O1 C11 1.365(2) . ? O2 C11 1.208(3) . ? O3 C13 1.221(2) . ? C1 C2 1.383(3) . ? C1 C6 1.387(3) . ? C2 C3 1.385(3) . ? C3 C4 1.384(3) . ? C4 C5 1.394(3) . ? C5 C6 1.391(3) . ? C5 C7 1.513(3) . ? C7 C8 1.533(3) . ? C7 C12 1.537(3) . ? C8 C9 1.497(3) . ? C9 C10 1.323(3) . ? C10 C11 1.468(3) . ? C12 C13 1.527(3) . ? C13 C14 1.488(3) . ? C14 C15 1.394(3) . ? C14 C19 1.391(3) . ? C15 C16 1.387(3) . ? C16 C17 1.388(3) . ? C17 C18 1.384(3) . ? C18 C19 1.392(3) . ? 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 O1 C8 C7 109.50(16) . . ? O1 C8 C9 103.62(16) . . ? O1 C11 C10 107.99(17) . . ? O2 C11 O1 121.8(2) . . ? O2 C11 C10 130.19(19) . . ? O3 C13 C12 119.77(19) . . ? O3 C13 C14 120.30(19) . . ? C1 C2 Cl2 121.33(16) . . ? C1 C6 C5 120.83(18) . . ? C2 C1 Cl1 120.89(16) . . ? C2 C1 C6 120.15(19) . . ? C2 C3 C4 119.81(19) . . ? C3 C2 Cl2 118.84(16) . . ? C3 C2 C1 119.81(18) . . ? C3 C4 C5 121.20(19) . . ? C4 C5 C7 121.80(18) . . ? C5 C7 C8 108.55(16) . . ? C5 C7 C12 113.26(16) . . ? C6 C1 Cl1 118.96(15) . . ? C6 C5 C4 118.18(18) . . ? C6 C5 C7 119.94(17) . . ? C8 C7 C12 110.02(16) . . ? C9 C8 C7 114.50(17) . . ? C9 C10 C11 108.71(19) . . ? C10 C9 C8 109.83(19) . . ? C11 O1 C8 109.77(15) . . ? C13 C12 C7 111.74(17) . . ? C14 C13 C12 119.90(17) . . ? C14 C19 C18 120.0(2) . . ? C15 C14 C13 117.95(18) . . ? C15 C16 C17 119.4(2) . . ? C16 C15 C14 120.8(2) . . ? C17 C18 C19 120.1(2) . . ? C18 C17 C16 120.4(2) . . ? C19 C14 C13 122.80(18) . . ? C19 C14 C15 119.25(19) . . ?