data_chai05s _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H18 O3' _chemical_formula_weight 270.31 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.612(3) _cell_length_b 20.668(9) _cell_length_c 9.542(3) _cell_angle_alpha 90.00 _cell_angle_beta 118.97(2) _cell_angle_gamma 90.00 _cell_volume 1313.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9674 _exptl_absorpt_correction_T_max 0.9908 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 8435 _diffrn_reflns_av_R_equivalents 0.1949 _diffrn_reflns_av_sigmaI/netI 0.1127 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 20.81 _reflns_number_total 1377 _reflns_number_gt 844 _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^)+(0.0543P)^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 1377 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1010 _refine_ls_R_factor_gt 0.0683 _refine_ls_wR_factor_ref 0.1495 _refine_ls_wR_factor_gt 0.1373 _refine_ls_goodness_of_fit_ref 0.913 _refine_ls_restrained_S_all 0.913 _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 0.7811(5) 1.04964(17) 0.8727(4) 0.0426(10) Uani 1 1 d . . . H5 H 0.9495 1.0492 0.9656 0.064 Uiso 1 1 d R . . O2 O 0.8237(5) 0.94673(17) 0.9383(4) 0.0430(11) Uani 1 1 d . . . O3 O 0.5316(5) 0.87872(16) 0.9060(4) 0.0422(11) Uani 1 1 d . . . H3A H 0.6501 0.8856 0.9253 0.063 Uiso 1 1 d R . . C1 C 0.4205(7) 1.2126(3) 0.6554(7) 0.0380(15) Uani 1 1 d . . . H1 H 0.4005 1.2533 0.6918 0.046 Uiso 1 1 calc R . . C2 C 0.4801(7) 1.2099(3) 0.5403(7) 0.0407(16) Uani 1 1 d . . . H2 H 0.5031 1.2485 0.4975 0.049 Uiso 1 1 calc R . . C3 C 0.5055(8) 1.1511(3) 0.4894(7) 0.0446(16) Uani 1 1 d . . . H3 H 0.5458 1.1489 0.4096 0.054 Uiso 1 1 calc R . . C4 C 0.4747(7) 1.0951(3) 0.5498(7) 0.0429(16) Uani 1 1 d . . . H4 H 0.4946 1.0544 0.5131 0.051 Uiso 1 1 calc R . . C5 C 0.4140(7) 1.0979(3) 0.6654(7) 0.0367(15) Uani 1 1 d . . . C6 C 0.3906(7) 1.1573(3) 0.7163(7) 0.0394(15) Uani 1 1 d . . . H6 H 0.3520 1.1599 0.7970 0.047 Uiso 1 1 calc R . . C7 C 0.3619(8) 1.0386(3) 0.7214(7) 0.0384(15) Uani 1 1 d . . . C8 C 0.1631(8) 1.0314(3) 0.6821(6) 0.0418(16) Uani 1 1 d . . . H8 H 0.0719 1.0658 0.6292 0.050 Uiso 1 1 calc R . . C9 C 0.0932(9) 0.9758(3) 0.7174(6) 0.0418(16) Uani 1 1 d . . . H9 H -0.0441 0.9735 0.6909 0.050 Uiso 1 1 calc R . . C10 C 0.2139(8) 0.9239(3) 0.7888(7) 0.0395(15) Uani 1 1 d . . . C11 C 0.4176(9) 0.9306(3) 0.8323(7) 0.0395(15) Uani 1 1 d . . . C12 C 0.4935(8) 0.9871(3) 0.8027(6) 0.0369(15) Uani 1 1 d . . . C13 C 0.7110(9) 0.9926(3) 0.8755(7) 0.0384(15) Uani 1 1 d . . . C14 C 0.1383(7) 0.8633(2) 0.8230(6) 0.0425(16) Uani 1 1 d . . . H14A H 0.0102 0.8728 0.8221 0.051 Uiso 1 1 calc R . . H14B H 0.2357 0.8487 0.9324 0.051 Uiso 1 1 calc R . . C15 C 0.1036(8) 0.8086(2) 0.7078(7) 0.0417(16) Uani 1 1 d . . . H15A H 0.0060 0.8227 0.5980 0.050 Uiso 1 1 calc R . . H15B H 0.2315 0.7983 0.7092 0.050 Uiso 1 1 calc R . . C16 C 0.0269(8) 0.7494(2) 0.7478(7) 0.0419(15) Uani 1 1 d . . . H16A H -0.1076 0.7587 0.7351 0.050 Uiso 1 1 calc R . . H16B H 0.1168 0.7385 0.8618 0.050 Uiso 1 1 calc R . . C17 C 0.0114(7) 0.6911(2) 0.6464(7) 0.0440(16) Uani 1 1 d . . . H17A H -0.0756 0.7015 0.5331 0.066 Uiso 1 1 calc R . . H17B H -0.0457 0.6547 0.6765 0.066 Uiso 1 1 calc R . . H17C H 0.1454 0.6795 0.6640 0.066 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 0.039(2) 0.039(2) 0.050(3) 0.0012(19) 0.022(2) -0.0041(19) O2 0.038(2) 0.035(2) 0.056(3) 0.003(2) 0.024(2) 0.004(2) O3 0.039(2) 0.038(2) 0.055(3) 0.003(2) 0.026(2) 0.002(2) C1 0.029(3) 0.040(4) 0.040(4) -0.002(3) 0.012(3) 0.004(3) C2 0.029(3) 0.040(4) 0.048(4) 0.005(3) 0.014(3) 0.003(3) C3 0.041(4) 0.042(4) 0.052(4) 0.005(4) 0.023(3) 0.003(3) C4 0.040(4) 0.042(4) 0.050(4) -0.004(3) 0.024(3) -0.006(3) C5 0.023(3) 0.035(4) 0.044(4) -0.003(3) 0.010(3) -0.002(3) C6 0.028(3) 0.042(4) 0.047(4) 0.008(3) 0.017(3) 0.001(3) C7 0.040(4) 0.033(4) 0.043(4) -0.009(3) 0.020(3) 0.001(3) C8 0.037(4) 0.044(4) 0.045(4) 0.001(3) 0.021(3) 0.003(3) C9 0.040(4) 0.040(4) 0.047(4) -0.005(3) 0.022(3) -0.004(3) C10 0.039(4) 0.035(4) 0.046(4) -0.005(3) 0.022(3) -0.001(3) C11 0.046(4) 0.033(4) 0.042(4) 0.002(3) 0.023(3) 0.009(3) C12 0.038(4) 0.036(4) 0.040(4) -0.001(3) 0.022(3) 0.000(3) C13 0.049(5) 0.032(4) 0.041(4) 0.000(3) 0.027(4) -0.005(3) C14 0.035(4) 0.042(4) 0.052(4) -0.004(3) 0.022(3) -0.002(3) C15 0.042(4) 0.038(4) 0.052(4) 0.002(3) 0.028(3) -0.001(3) C16 0.032(3) 0.039(4) 0.055(4) -0.002(3) 0.021(3) -0.003(3) C17 0.033(4) 0.042(4) 0.062(4) 0.001(3) 0.027(3) 0.004(3) _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 C13 1.300(6) . ? O2 C13 1.222(6) . ? O3 C11 1.344(6) . ? C1 C6 1.351(7) . ? C1 C2 1.377(7) . ? C2 C3 1.356(7) . ? C3 C4 1.364(7) . ? C4 C5 1.387(7) . ? C5 C6 1.364(7) . ? C5 C7 1.466(7) . ? C7 C8 1.380(7) . ? C7 C12 1.409(7) . ? C8 C9 1.374(6) . ? C9 C10 1.361(7) . ? C10 C11 1.405(7) . ? C10 C14 1.479(7) . ? C11 C12 1.391(7) . ? C12 C13 1.457(7) . ? C14 C15 1.509(7) . ? C15 C16 1.483(6) . ? C16 C17 1.513(7) . ? 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 C6 C1 C2 119.9(5) . . ? C3 C2 C1 118.8(5) . . ? C2 C3 C4 121.7(6) . . ? C3 C4 C5 119.5(5) . . ? C6 C5 C4 118.2(5) . . ? C6 C5 C7 121.2(5) . . ? C4 C5 C7 120.5(5) . . ? C1 C6 C5 122.0(5) . . ? C8 C7 C12 117.5(5) . . ? C8 C7 C5 116.5(5) . . ? C12 C7 C5 125.9(5) . . ? C9 C8 C7 121.9(5) . . ? C10 C9 C8 122.3(5) . . ? C9 C10 C11 116.8(5) . . ? C9 C10 C14 122.5(5) . . ? C11 C10 C14 120.7(5) . . ? O3 C11 C12 123.3(5) . . ? O3 C11 C10 114.6(5) . . ? C12 C11 C10 122.0(5) . . ? C11 C12 C7 119.4(5) . . ? C11 C12 C13 117.1(5) . . ? C7 C12 C13 123.0(5) . . ? O2 C13 O1 121.0(5) . . ? O2 C13 C12 122.6(5) . . ? O1 C13 C12 116.3(5) . . ? C10 C14 C15 115.0(4) . . ? C16 C15 C14 112.5(4) . . ? C15 C16 C17 114.2(4) . . ? 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 0.7(7) . . . . ? C1 C2 C3 C4 -0.4(8) . . . . ? C2 C3 C4 C5 0.6(8) . . . . ? C3 C4 C5 C6 -1.0(7) . . . . ? C3 C4 C5 C7 174.3(5) . . . . ? C2 C1 C6 C5 -1.2(8) . . . . ? C4 C5 C6 C1 1.4(8) . . . . ? C7 C5 C6 C1 -173.9(5) . . . . ? C6 C5 C7 C8 62.6(7) . . . . ? C4 C5 C7 C8 -112.6(6) . . . . ? C6 C5 C7 C12 -121.4(6) . . . . ? C4 C5 C7 C12 63.4(8) . . . . ? C12 C7 C8 C9 -1.3(8) . . . . ? C5 C7 C8 C9 175.0(5) . . . . ? C7 C8 C9 C10 -1.9(8) . . . . ? C8 C9 C10 C11 2.8(8) . . . . ? C8 C9 C10 C14 -178.3(5) . . . . ? C9 C10 C11 O3 178.4(5) . . . . ? C14 C10 C11 O3 -0.5(7) . . . . ? C9 C10 C11 C12 -0.6(8) . . . . ? C14 C10 C11 C12 -179.6(5) . . . . ? O3 C11 C12 C7 178.6(5) . . . . ? C10 C11 C12 C7 -2.5(8) . . . . ? O3 C11 C12 C13 -8.7(8) . . . . ? C10 C11 C12 C13 170.3(5) . . . . ? C8 C7 C12 C11 3.4(8) . . . . ? C5 C7 C12 C11 -172.6(5) . . . . ? C8 C7 C12 C13 -169.0(5) . . . . ? C5 C7 C12 C13 15.1(9) . . . . ? C11 C12 C13 O2 11.5(8) . . . . ? C7 C12 C13 O2 -176.0(5) . . . . ? C11 C12 C13 O1 -167.4(5) . . . . ? C7 C12 C13 O1 5.1(8) . . . . ? C9 C10 C14 C15 102.1(6) . . . . ? C11 C10 C14 C15 -79.0(6) . . . . ? C10 C14 C15 C16 -179.7(5) . . . . ? C14 C15 C16 C17 -173.7(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 20.81 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.242 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.058