# 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_email okdnypps@yahoo.com.tw _publ_contact_author_name 'Jung-Hsuan Chen' loop_ _publ_author_name 'Jung-Hsuan Chen' 'Chihliang Chang' 'Hui-Ju Chang' 'Kwunmin Chen' data_a11374 _database_code_depnum_ccdc_archive 'CCDC 824118' #TrackingRef '5247_web_deposit_cif_file_0_Jung-HsuanChen_1304497650.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (E)-1-((E)-3-(4-nitrophenyl)allylidene)- 3,4-dihydronaphthalen-2(1H)-one ; _chemical_name_common ? _chemical_melting_point 463.4(2) _chemical_formula_moiety 'C19 H15 N O3' _chemical_formula_sum 'C19 H15 N O3' _chemical_formula_weight 305.32 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' N N 0.0061 0.0033 '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 orthorhombic _symmetry_space_group_name_H-M 'P b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.5097(5) _cell_length_b 14.8345(10) _cell_length_c 27.016(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3009.6(4) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.72 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9369 _exptl_absorpt_correction_T_max 0.9900 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 18103 _diffrn_reflns_av_R_equivalents 0.0547 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2631 _reflns_number_gt 1947 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0552P)^2^+0.3798P] 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 fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2631 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1065 _refine_ls_wR_factor_gt 0.0956 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.001 _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 C1 C 0.1379(2) 0.55378(11) 1.08366(6) 0.0366(4) Uani 1 1 d . . . C2 C 0.0995(2) 0.63391(12) 1.10710(6) 0.0404(4) Uani 1 1 d . . . H2 H 0.0811 0.6358 1.1419 0.048 Uiso 1 1 calc R . . C3 C 0.0883(2) 0.71128(12) 1.07906(6) 0.0393(4) Uani 1 1 d . . . H3 H 0.0605 0.7667 1.0948 0.047 Uiso 1 1 calc R . . C4 C 0.1170(2) 0.71005(11) 1.02803(6) 0.0347(4) Uani 1 1 d . . . C5 C 0.1556(2) 0.62721(12) 1.00558(6) 0.0402(4) Uani 1 1 d . . . H5 H 0.1757 0.6249 0.9709 0.048 Uiso 1 1 calc R . . C6 C 0.1648(2) 0.54897(12) 1.03305(6) 0.0422(5) Uani 1 1 d . . . H6 H 0.1892 0.4928 1.0175 0.051 Uiso 1 1 calc R . . C7 C 0.1035(2) 0.79419(12) 1.00060(6) 0.0388(4) Uani 1 1 d . . . H7 H 0.0767 0.8464 1.0195 0.047 Uiso 1 1 calc R . . C8 C 0.1246(2) 0.80692(12) 0.95161(6) 0.0385(4) Uani 1 1 d . . . H8 H 0.1534 0.7570 0.9311 0.046 Uiso 1 1 calc R . . C9 C 0.1041(2) 0.89471(12) 0.92982(6) 0.0384(4) Uani 1 1 d . . . H9 H 0.0899 0.9423 0.9530 0.046 Uiso 1 1 calc R . . C10 C 0.1015(2) 0.92102(11) 0.88172(6) 0.0339(4) Uani 1 1 d . . . C11 C 0.1036(2) 0.86164(11) 0.83782(6) 0.0314(4) Uani 1 1 d . . . C12 C 0.0287(2) 0.77512(11) 0.83805(6) 0.0357(4) Uani 1 1 d . . . H12 H -0.0274 0.7534 0.8672 0.043 Uiso 1 1 calc R . . C13 C 0.0353(2) 0.72089(12) 0.79650(6) 0.0416(4) Uani 1 1 d . . . H13 H -0.0151 0.6622 0.7974 0.050 Uiso 1 1 calc R . . C14 C 0.1152(2) 0.75196(12) 0.75368(7) 0.0436(5) Uani 1 1 d . . . H14 H 0.1227 0.7142 0.7254 0.052 Uiso 1 1 calc R . . C15 C 0.1840(2) 0.83813(11) 0.75230(6) 0.0401(4) Uani 1 1 d . . . H15 H 0.2367 0.8596 0.7226 0.048 Uiso 1 1 calc R . . C16 C 0.1779(2) 0.89404(11) 0.79333(6) 0.0330(4) Uani 1 1 d . . . C17 C 0.2452(2) 0.98965(11) 0.79122(6) 0.0407(4) Uani 1 1 d . . . H17A H 0.2513 1.0098 0.7563 0.049 Uiso 1 1 calc R . . H17B H 0.3667 0.9926 0.8053 0.049 Uiso 1 1 calc R . . C18 C 0.1217(2) 1.05191(11) 0.82030(6) 0.0389(4) Uani 1 1 d . . . H18A H 0.1716 1.1137 0.8203 0.047 Uiso 1 1 calc R . . H18B H 0.0040 1.0541 0.8038 0.047 Uiso 1 1 calc R . . C19 C 0.0982(2) 1.02066(11) 0.87260(6) 0.0391(4) Uani 1 1 d . . . N1 N 0.15128(19) 0.47111(10) 1.11284(6) 0.0460(4) Uani 1 1 d . . . O1 O 0.17336(18) 0.47824(9) 1.15796(5) 0.0582(4) Uani 1 1 d . . . O2 O 0.14122(19) 0.39818(9) 1.09136(5) 0.0670(4) Uani 1 1 d . . . O3 O 0.0781(2) 1.07477(9) 0.90627(5) 0.0632(4) Uani 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 0.0305(10) 0.0464(10) 0.0328(10) 0.0060(8) -0.0014(7) -0.0016(7) C2 0.0446(11) 0.0511(11) 0.0255(9) 0.0019(8) 0.0010(7) -0.0014(8) C3 0.0460(11) 0.0440(10) 0.0278(10) -0.0018(8) 0.0008(8) -0.0010(8) C4 0.0321(9) 0.0468(10) 0.0253(9) 0.0010(8) -0.0012(7) -0.0018(7) C5 0.0422(11) 0.0526(11) 0.0258(9) -0.0014(8) 0.0006(7) 0.0007(8) C6 0.0424(11) 0.0467(11) 0.0376(10) -0.0040(9) 0.0006(8) 0.0024(8) C7 0.0390(10) 0.0483(10) 0.0290(10) 0.0003(8) 0.0004(8) 0.0013(8) C8 0.0376(10) 0.0478(11) 0.0301(10) 0.0006(8) -0.0003(7) 0.0048(7) C9 0.0384(10) 0.0462(10) 0.0306(10) -0.0031(8) 0.0013(7) 0.0041(8) C10 0.0319(10) 0.0415(9) 0.0282(9) 0.0019(8) 0.0005(7) 0.0030(7) C11 0.0281(9) 0.0376(9) 0.0286(9) 0.0017(7) -0.0024(7) 0.0042(7) C12 0.0362(10) 0.0368(9) 0.0340(10) 0.0069(8) -0.0041(7) 0.0039(7) C13 0.0417(11) 0.0345(9) 0.0485(12) -0.0010(8) -0.0092(9) 0.0051(8) C14 0.0456(11) 0.0462(11) 0.0389(11) -0.0108(9) -0.0028(9) 0.0063(8) C15 0.0404(11) 0.0505(11) 0.0295(9) -0.0023(8) 0.0020(8) 0.0027(8) C16 0.0285(9) 0.0416(9) 0.0290(9) -0.0008(7) -0.0014(7) 0.0013(7) C17 0.0402(11) 0.0483(10) 0.0338(9) 0.0018(8) 0.0032(8) -0.0085(8) C18 0.0457(11) 0.0357(9) 0.0352(10) 0.0041(8) -0.0005(8) -0.0060(7) C19 0.0404(11) 0.0416(10) 0.0353(10) -0.0039(8) -0.0012(8) 0.0028(8) N1 0.0436(10) 0.0482(10) 0.0463(10) 0.0062(8) 0.0018(7) 0.0022(7) O1 0.0691(10) 0.0664(9) 0.0393(8) 0.0135(7) 0.0002(7) 0.0062(7) O2 0.0900(12) 0.0462(9) 0.0649(10) 0.0048(7) -0.0018(8) -0.0002(7) O3 0.1020(12) 0.0476(8) 0.0399(8) -0.0101(7) 0.0011(7) 0.0117(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 C1 C2 1.377(2) . ? C1 C6 1.384(2) . ? C1 N1 1.461(2) . ? C2 C3 1.378(2) . ? C2 H2 0.9500 . ? C3 C4 1.395(2) . ? C3 H3 0.9500 . ? C4 C5 1.401(2) . ? C4 C7 1.455(2) . ? C5 C6 1.379(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.346(2) . ? C7 H7 0.9500 . ? C8 C9 1.437(2) . ? C8 H8 0.9500 . ? C9 C10 1.357(2) . ? C9 H9 0.9500 . ? C10 C11 1.478(2) . ? C10 C19 1.499(2) . ? C11 C12 1.401(2) . ? C11 C16 1.409(2) . ? C12 C13 1.382(2) . ? C12 H12 0.9500 . ? C13 C14 1.382(2) . ? C13 H13 0.9500 . ? C14 C15 1.379(2) . ? C14 H14 0.9500 . ? C15 C16 1.385(2) . ? C15 H15 0.9500 . ? C16 C17 1.507(2) . ? C17 C18 1.527(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.497(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 O3 1.2224(19) . ? N1 O2 1.2300(19) . ? N1 O1 1.2350(18) . ? 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 C2 C1 C6 121.96(16) . . ? C2 C1 N1 119.38(15) . . ? C6 C1 N1 118.66(16) . . ? C1 C2 C3 118.60(16) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C2 C3 C4 121.54(16) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C3 C4 C5 118.10(15) . . ? C3 C4 C7 118.77(16) . . ? C5 C4 C7 123.12(15) . . ? C6 C5 C4 121.05(15) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C1 118.73(16) . . ? C5 C6 H6 120.6 . . ? C1 C6 H6 120.6 . . ? C8 C7 C4 127.81(17) . . ? C8 C7 H7 116.1 . . ? C4 C7 H7 116.1 . . ? C7 C8 C9 121.15(16) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C10 C9 C8 130.87(16) . . ? C10 C9 H9 114.6 . . ? C8 C9 H9 114.6 . . ? C9 C10 C11 126.66(15) . . ? C9 C10 C19 116.20(15) . . ? C11 C10 C19 117.14(14) . . ? C12 C11 C16 118.36(14) . . ? C12 C11 C10 122.55(14) . . ? C16 C11 C10 119.05(14) . . ? C13 C12 C11 121.01(16) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C14 120.08(16) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C15 C14 C13 119.63(16) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C16 121.38(16) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C15 C16 C11 119.43(15) . . ? C15 C16 C17 121.47(14) . . ? C11 C16 C17 119.08(14) . . ? C16 C17 C18 110.24(14) . . ? C16 C17 H17A 109.6 . . ? C18 C17 H17A 109.6 . . ? C16 C17 H17B 109.6 . . ? C18 C17 H17B 109.6 . . ? H17A C17 H17B 108.1 . . ? C19 C18 C17 111.70(14) . . ? C19 C18 H18A 109.3 . . ? C17 C18 H18A 109.3 . . ? C19 C18 H18B 109.3 . . ? C17 C18 H18B 109.3 . . ? H18A C18 H18B 107.9 . . ? O3 C19 C10 121.82(16) . . ? O3 C19 C18 120.89(16) . . ? C10 C19 C18 117.29(14) . . ? O2 N1 O1 123.32(16) . . ? O2 N1 C1 118.66(16) . . ? O1 N1 C1 118.02(15) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.168 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.038 # Attachment '5248_web_deposit_cif_file_1_Jung-HsuanChen_1304497650.cif' data_12106 _database_code_depnum_ccdc_archive 'CCDC 824119' #TrackingRef '5248_web_deposit_cif_file_1_Jung-HsuanChen_1304497650.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-phenyl-5,6-dihydro-1H-benzo[f]chromen -3(2H)-one ; _chemical_name_common ? _chemical_melting_point 432.4(2) _chemical_formula_moiety 'C19 H16 O2' _chemical_formula_sum 'C19 H16 O2' _chemical_formula_weight 276.32 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.93500(10) _cell_length_b 14.0588(3) _cell_length_c 17.2947(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1443.05(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6406 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8412 _exptl_absorpt_correction_T_max 1.0641 _exptl_absorpt_process_details ; ? ; _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 KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9445 _diffrn_reflns_av_R_equivalents 0.0555 _diffrn_reflns_av_sigmaI/netI 0.0453 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2532 _reflns_number_gt 1962 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0640P)^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 fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.47(2) _refine_ls_number_reflns 2532 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0745 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.1232 _refine_ls_wR_factor_gt 0.1014 _refine_ls_goodness_of_fit_ref 1.155 _refine_ls_restrained_S_all 1.155 _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 0.1428(3) -0.08533(12) 0.31627(9) 0.0560(5) Uani 1 1 d . . . O2 O 0.0445(4) -0.12371(16) 0.19817(11) 0.0800(7) Uani 1 1 d . . . C1 C 0.1958(5) -0.10029(19) 0.24027(14) 0.0560(7) Uani 1 1 d . . . C2 C 0.4363(5) -0.09050(19) 0.21951(14) 0.0553(7) Uani 1 1 d . . . H2A H 0.4507 -0.0892 0.1637 0.066 Uiso 1 1 calc R . . H2B H 0.5184 -0.1454 0.2385 0.066 Uiso 1 1 calc R . . C3 C 0.5408(5) 0.00024(16) 0.25343(13) 0.0472(6) Uani 1 1 d . . . H3 H 0.7050 -0.0053 0.2491 0.057 Uiso 1 1 calc R . . C4 C 0.4680(4) 0.08780(17) 0.20779(12) 0.0442(6) Uani 1 1 d . . . C5 C 0.5986(5) 0.1208(2) 0.14735(15) 0.0635(8) Uani 1 1 d . . . H5 H 0.7341 0.0907 0.1360 0.076 Uiso 1 1 calc R . . C6 C 0.5310(7) 0.1984(2) 0.10312(16) 0.0786(10) Uani 1 1 d . . . H6 H 0.6217 0.2202 0.0630 0.094 Uiso 1 1 calc R . . C7 C 0.3319(7) 0.2421(2) 0.11875(18) 0.0750(10) Uani 1 1 d . . . H7 H 0.2856 0.2936 0.0890 0.090 Uiso 1 1 calc R . . C8 C 0.2002(6) 0.2107(2) 0.17778(17) 0.0720(9) Uani 1 1 d . . . H8 H 0.0640 0.2407 0.1882 0.086 Uiso 1 1 calc R . . C9 C 0.2685(5) 0.13404(18) 0.22246(16) 0.0594(7) Uani 1 1 d . . . H9 H 0.1778 0.1136 0.2630 0.071 Uiso 1 1 calc R . . C10 C 0.4822(4) 0.00471(16) 0.33821(13) 0.0431(6) Uani 1 1 d . . . C11 C 0.2998(4) -0.03986(16) 0.36455(13) 0.0452(6) Uani 1 1 d . . . C12 C 0.2241(5) -0.0404(2) 0.44677(14) 0.0542(7) Uani 1 1 d . . . H12A H 0.1508 -0.1004 0.4583 0.065 Uiso 1 1 calc R . . H12B H 0.1157 0.0103 0.4550 0.065 Uiso 1 1 calc R . . C13 C 0.4244(5) -0.02666(19) 0.50032(14) 0.0556(7) Uani 1 1 d . . . H13A H 0.3699 -0.0100 0.5514 0.067 Uiso 1 1 calc R . . H13B H 0.5056 -0.0863 0.5046 0.067 Uiso 1 1 calc R . . C14 C 0.5835(4) 0.04913(16) 0.47303(13) 0.0452(6) Uani 1 1 d . . . C15 C 0.6150(4) 0.06160(16) 0.39325(12) 0.0430(6) Uani 1 1 d . . . C16 C 0.7685(4) 0.13014(17) 0.36823(15) 0.0534(7) Uani 1 1 d . . . H16 H 0.7901 0.1394 0.3155 0.064 Uiso 1 1 calc R . . C17 C 0.8885(5) 0.18442(19) 0.42017(15) 0.0610(7) Uani 1 1 d . . . H17 H 0.9900 0.2299 0.4025 0.073 Uiso 1 1 calc R . . C18 C 0.8579(5) 0.17119(19) 0.49831(15) 0.0593(7) Uani 1 1 d . . . H18 H 0.9396 0.2073 0.5336 0.071 Uiso 1 1 calc R . . C19 C 0.7064(5) 0.10455(18) 0.52399(13) 0.0538(7) Uani 1 1 d . . . H19 H 0.6858 0.0964 0.5769 0.065 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 0.0553(11) 0.0635(11) 0.0491(10) -0.0024(9) -0.0027(9) -0.0104(10) O2 0.0787(16) 0.0980(16) 0.0633(12) -0.0108(10) -0.0178(12) -0.0095(12) C1 0.0688(19) 0.0517(15) 0.0476(15) -0.0052(11) -0.0097(15) 0.0020(14) C2 0.0657(18) 0.0570(15) 0.0431(13) -0.0074(12) 0.0005(13) 0.0157(14) C3 0.0426(14) 0.0606(16) 0.0384(13) -0.0042(11) 0.0039(11) 0.0076(12) C4 0.0459(14) 0.0534(14) 0.0334(11) -0.0031(10) 0.0015(11) -0.0015(12) C5 0.0655(18) 0.078(2) 0.0468(15) -0.0007(14) 0.0128(14) -0.0062(16) C6 0.105(3) 0.082(2) 0.0485(17) 0.0127(16) 0.0055(19) -0.029(2) C7 0.100(3) 0.0596(18) 0.065(2) 0.0112(14) -0.021(2) -0.0102(19) C8 0.074(2) 0.0617(17) 0.080(2) 0.0028(16) -0.0097(18) 0.0092(16) C9 0.0560(17) 0.0632(16) 0.0590(16) 0.0084(13) 0.0061(14) 0.0079(14) C10 0.0415(14) 0.0490(14) 0.0387(12) -0.0005(10) -0.0003(11) 0.0054(11) C11 0.0463(15) 0.0496(13) 0.0397(13) -0.0011(10) -0.0035(12) 0.0003(12) C12 0.0550(16) 0.0621(15) 0.0454(14) 0.0061(11) 0.0057(13) -0.0042(14) C13 0.0653(18) 0.0633(16) 0.0381(13) 0.0023(12) 0.0033(13) -0.0004(14) C14 0.0489(15) 0.0488(14) 0.0377(13) 0.0010(10) 0.0016(11) 0.0088(12) C15 0.0416(13) 0.0500(13) 0.0375(12) -0.0001(10) 0.0023(11) 0.0050(11) C16 0.0514(16) 0.0636(16) 0.0451(13) 0.0047(11) 0.0002(13) -0.0029(14) C17 0.0580(17) 0.0632(16) 0.0617(17) 0.0042(14) -0.0040(14) -0.0086(14) C18 0.0644(19) 0.0593(17) 0.0542(16) -0.0110(13) -0.0074(14) -0.0026(14) C19 0.0626(17) 0.0604(16) 0.0385(13) -0.0047(12) -0.0036(13) 0.0084(14) _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 1.368(3) . ? O1 C11 1.405(3) . ? O2 C1 1.202(3) . ? C1 C2 1.478(4) . ? C2 C3 1.535(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C10 1.508(3) . ? C3 C4 1.525(3) . ? C3 H3 0.9800 . ? C4 C9 1.374(4) . ? C4 C5 1.382(3) . ? C5 C6 1.390(4) . ? C5 H5 0.9300 . ? C6 C7 1.360(5) . ? C6 H6 0.9300 . ? C7 C8 1.359(4) . ? C7 H7 0.9300 . ? C8 C9 1.387(4) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.331(3) . ? C10 C15 1.472(3) . ? C11 C12 1.491(3) . ? C12 C13 1.519(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.500(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C19 1.384(3) . ? C14 C15 1.403(3) . ? C15 C16 1.395(3) . ? C16 C17 1.377(4) . ? C16 H16 0.9300 . ? C17 C18 1.376(4) . ? C17 H17 0.9300 . ? C18 C19 1.372(4) . ? C18 H18 0.9300 . ? C19 H19 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 C11 119.3(2) . . ? O2 C1 O1 116.9(3) . . ? O2 C1 C2 126.8(2) . . ? O1 C1 C2 116.2(2) . . ? C1 C2 C3 112.0(2) . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C10 C3 C4 113.84(18) . . ? C10 C3 C2 108.2(2) . . ? C4 C3 C2 111.00(19) . . ? C10 C3 H3 107.9 . . ? C4 C3 H3 107.9 . . ? C2 C3 H3 107.9 . . ? C9 C4 C5 117.6(2) . . ? C9 C4 C3 122.0(2) . . ? C5 C4 C3 120.3(2) . . ? C4 C5 C6 121.2(3) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C7 C6 C5 119.7(3) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C8 C7 C6 120.1(3) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 120.2(3) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C4 C9 C8 121.1(3) . . ? C4 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C11 C10 C15 118.0(2) . . ? C11 C10 C3 120.0(2) . . ? C15 C10 C3 121.8(2) . . ? C10 C11 O1 123.4(2) . . ? C10 C11 C12 125.0(2) . . ? O1 C11 C12 111.4(2) . . ? C11 C12 C13 110.2(2) . . ? C11 C12 H12A 109.6 . . ? C13 C12 H12A 109.6 . . ? C11 C12 H12B 109.6 . . ? C13 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? C14 C13 C12 113.03(19) . . ? C14 C13 H13A 109.0 . . ? C12 C13 H13A 109.0 . . ? C14 C13 H13B 109.0 . . ? C12 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C19 C14 C15 119.0(2) . . ? C19 C14 C13 122.1(2) . . ? C15 C14 C13 118.8(2) . . ? C16 C15 C14 118.6(2) . . ? C16 C15 C10 121.6(2) . . ? C14 C15 C10 119.8(2) . . ? C17 C16 C15 121.2(2) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C18 C17 C16 119.8(3) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C19 C18 C17 119.8(3) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C18 C19 C14 121.6(2) . . ? C18 C19 H19 119.2 . . ? C14 C19 H19 119.2 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.247 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.116