data_b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _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 Monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 17.095(3) _cell_length_b 5.8740(12) _cell_length_c 15.476(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.00(3) _cell_angle_gamma 90.00 _cell_volume 1493.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 12 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.229 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9768 _exptl_absorpt_correction_T_max 0.9922 _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 'Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_decay_% 1 _diffrn_reflns_number 3013 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0536 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 25.40 _reflns_number_total 1511 _reflns_number_gt 1064 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 EXPRESS(Enraf-Nonius,1994)' _computing_cell_refinement 'CAD4 EXPRESS' _computing_data_reduction 'XCAD4(Harms & Wocadlo,1995)' _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^)+(0.0820P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.014(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -3(3) _refine_ls_number_reflns 1511 _refine_ls_number_parameters 191 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0778 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1435 _refine_ls_wR_factor_gt 0.1258 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 C1 C 0.1838(2) 0.4720(8) 0.8090(2) 0.0562(10) Uani 1 1 d . . . H1A H 0.1934 0.6100 0.7843 0.067 Uiso 1 1 calc R . . O1 O -0.0796(2) 0.8229(7) 0.6275(2) 0.0880(11) Uani 1 1 d . . . C2 C 0.2510(2) 0.3344(7) 0.8533(2) 0.0517(10) Uani 1 1 d . . . O2 O -0.09413(15) 0.5669(5) 0.51683(17) 0.0653(8) Uani 1 1 d . . . C3 C 0.3322(2) 0.4004(9) 0.8612(3) 0.0651(12) Uani 1 1 d . . . H3A H 0.3424 0.5377 0.8364 0.078 Uiso 1 1 calc R . . C4 C 0.3955(3) 0.2658(11) 0.9045(3) 0.0786(15) Uani 1 1 d . . . H4A H 0.4487 0.3118 0.9096 0.094 Uiso 1 1 calc R . . C5 C 0.3810(3) 0.0584(11) 0.9415(3) 0.0819(16) Uani 1 1 d . . . H5A H 0.4245 -0.0340 0.9704 0.098 Uiso 1 1 calc R . . C6 C 0.3037(3) -0.0090(9) 0.9354(3) 0.0714(13) Uani 1 1 d . . . H6A H 0.2947 -0.1458 0.9614 0.086 Uiso 1 1 calc R . . C7 C 0.2369(2) 0.1261(7) 0.8900(2) 0.0526(10) Uani 1 1 d . . . C8 C 0.1555(2) 0.0609(8) 0.8822(3) 0.0623(11) Uani 1 1 d . . . H8A H 0.1449 -0.0763 0.9068 0.075 Uiso 1 1 calc R . . C9 C 0.0931(3) 0.1971(8) 0.8391(3) 0.0640(12) Uani 1 1 d . . . H9A H 0.0401 0.1497 0.8341 0.077 Uiso 1 1 calc R . . C10 C 0.1056(2) 0.4090(8) 0.8015(2) 0.0582(11) Uani 1 1 d . . . C11 C 0.0342(3) 0.5552(10) 0.7514(3) 0.0761(14) Uani 1 1 d . . . H11A H 0.0518 0.7124 0.7524 0.091 Uiso 1 1 calc R . . H11B H -0.0082 0.5473 0.7819 0.091 Uiso 1 1 calc R . . C12 C -0.0004(2) 0.4797(8) 0.6543(2) 0.0581(11) Uani 1 1 d . . . H12A H 0.0437 0.4648 0.6264 0.070 Uiso 1 1 calc R . . H12B H -0.0256 0.3315 0.6532 0.070 Uiso 1 1 calc R . . C13 C -0.0619(2) 0.6447(8) 0.6014(3) 0.0561(10) Uani 1 1 d . . . C14 C -0.1530(2) 0.7018(7) 0.4567(2) 0.0528(11) Uani 1 1 d . . . C15 C -0.2299(2) 0.6141(8) 0.4261(3) 0.0572(11) Uani 1 1 d . . . H15A H -0.2433 0.4766 0.4483 0.069 Uiso 1 1 calc R . . C16 C -0.2876(2) 0.7344(8) 0.3615(3) 0.0600(11) Uani 1 1 d . . . H16A H -0.3402 0.6776 0.3399 0.072 Uiso 1 1 calc R . . C17 C -0.2672(2) 0.9364(9) 0.3296(3) 0.0617(12) Uani 1 1 d . . . H17A H -0.3061 1.0168 0.2865 0.074 Uiso 1 1 calc R . . C18 C -0.1902(2) 1.0209(9) 0.3603(3) 0.0707(13) Uani 1 1 d . . . H18A H -0.1767 1.1579 0.3379 0.085 Uiso 1 1 calc R . . C19 C -0.1325(2) 0.9030(8) 0.4245(3) 0.0651(12) Uani 1 1 d . . . H19A H -0.0799 0.9600 0.4457 0.078 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 C1 0.072(3) 0.048(2) 0.049(2) 0.005(2) 0.0169(18) 0.004(2) O1 0.097(2) 0.081(3) 0.074(2) -0.010(2) 0.0034(16) 0.035(2) C2 0.063(2) 0.050(3) 0.0400(19) -0.0058(19) 0.0107(17) 0.000(2) O2 0.0667(15) 0.066(2) 0.0585(16) 0.0041(16) 0.0094(12) 0.0195(16) C3 0.071(3) 0.070(3) 0.053(2) -0.002(2) 0.0159(19) -0.004(3) C4 0.066(3) 0.099(4) 0.067(3) -0.008(3) 0.011(2) 0.004(3) C5 0.071(3) 0.098(4) 0.071(3) 0.006(3) 0.010(2) 0.025(3) C6 0.098(3) 0.059(3) 0.054(2) 0.010(2) 0.014(2) 0.019(3) C7 0.068(2) 0.052(3) 0.0363(17) -0.0013(19) 0.0122(17) 0.007(2) C8 0.085(3) 0.050(2) 0.052(2) -0.002(2) 0.018(2) -0.003(3) C9 0.063(2) 0.070(3) 0.058(3) -0.007(2) 0.017(2) -0.011(3) C10 0.067(3) 0.058(3) 0.045(2) -0.010(2) 0.0076(18) 0.010(2) C11 0.077(3) 0.083(4) 0.063(2) -0.005(3) 0.012(2) 0.023(3) C12 0.051(2) 0.067(3) 0.057(2) 0.000(2) 0.0156(17) 0.005(2) C13 0.048(2) 0.059(3) 0.064(2) 0.006(2) 0.0190(18) 0.007(2) C14 0.053(2) 0.056(3) 0.052(2) 0.007(2) 0.0184(17) 0.011(2) C15 0.060(2) 0.054(3) 0.063(2) 0.001(2) 0.0266(19) -0.003(2) C16 0.052(2) 0.072(3) 0.055(2) 0.003(2) 0.0130(19) 0.006(2) C17 0.061(3) 0.070(3) 0.053(2) 0.012(2) 0.0158(18) 0.017(2) C18 0.077(3) 0.070(3) 0.069(3) 0.020(3) 0.028(2) 0.001(3) C19 0.052(2) 0.069(3) 0.073(3) 0.009(3) 0.016(2) 0.001(2) _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 C10 1.360(5) . ? C1 C2 1.418(5) . ? C1 H1A 0.9300 . ? O1 C13 1.191(5) . ? C2 C7 1.398(6) . ? C2 C3 1.414(5) . ? O2 C13 1.352(5) . ? O2 C14 1.411(4) . ? C3 C4 1.359(6) . ? C3 H3A 0.9300 . ? C4 C5 1.397(8) . ? C4 H4A 0.9300 . ? C5 C6 1.357(6) . ? C5 H5A 0.9300 . ? C6 C7 1.409(5) . ? C6 H6A 0.9300 . ? C7 C8 1.415(5) . ? C8 C9 1.354(6) . ? C8 H8A 0.9300 . ? C9 C10 1.415(6) . ? C9 H9A 0.9300 . ? C10 C11 1.519(6) . ? C11 C12 1.521(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.497(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C14 C19 1.366(6) . ? C14 C15 1.369(5) . ? C15 C16 1.389(6) . ? C15 H15A 0.9300 . ? C16 C17 1.367(7) . ? C16 H16A 0.9300 . ? C17 C18 1.363(6) . ? C17 H17A 0.9300 . ? C18 C19 1.379(5) . ? 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 C10 C1 C2 122.2(4) . . ? C10 C1 H1A 118.9 . . ? C2 C1 H1A 118.9 . . ? C7 C2 C3 118.7(4) . . ? C7 C2 C1 119.2(4) . . ? C3 C2 C1 122.1(4) . . ? C13 O2 C14 118.3(3) . . ? C4 C3 C2 120.9(5) . . ? C4 C3 H3A 119.6 . . ? C2 C3 H3A 119.6 . . ? C3 C4 C5 120.1(5) . . ? C3 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? C6 C5 C4 120.4(5) . . ? C6 C5 H5A 119.8 . . ? C4 C5 H5A 119.8 . . ? C5 C6 C7 120.7(5) . . ? C5 C6 H6A 119.7 . . ? C7 C6 H6A 119.7 . . ? C2 C7 C6 119.2(4) . . ? C2 C7 C8 118.6(4) . . ? C6 C7 C8 122.2(4) . . ? C9 C8 C7 120.3(4) . . ? C9 C8 H8A 119.8 . . ? C7 C8 H8A 119.8 . . ? C8 C9 C10 122.3(4) . . ? C8 C9 H9A 118.9 . . ? C10 C9 H9A 118.9 . . ? C1 C10 C9 117.4(4) . . ? C1 C10 C11 121.5(4) . . ? C9 C10 C11 121.1(4) . . ? C10 C11 C12 112.2(4) . . ? C10 C11 H11A 109.2 . . ? C12 C11 H11A 109.2 . . ? C10 C11 H11B 109.2 . . ? C12 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? C13 C12 C11 112.0(4) . . ? C13 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? C13 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? O1 C13 O2 123.5(4) . . ? O1 C13 C12 126.1(4) . . ? O2 C13 C12 110.4(4) . . ? C19 C14 C15 121.3(4) . . ? C19 C14 O2 121.2(4) . . ? C15 C14 O2 117.3(4) . . ? C14 C15 C16 118.7(4) . . ? C14 C15 H15A 120.6 . . ? C16 C15 H15A 120.6 . . ? C17 C16 C15 120.0(4) . . ? C17 C16 H16A 120.0 . . ? C15 C16 H16A 120.0 . . ? C18 C17 C16 120.6(4) . . ? C18 C17 H17A 119.7 . . ? C16 C17 H17A 119.7 . . ? C17 C18 C19 119.9(4) . . ? C17 C18 H18A 120.0 . . ? C19 C18 H18A 120.0 . . ? C14 C19 C18 119.5(4) . . ? C14 C19 H19A 120.3 . . ? C18 C19 H19A 120.3 . . ? 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 C10 C1 C2 C7 0.5(5) . . . . ? C10 C1 C2 C3 -179.9(4) . . . . ? C7 C2 C3 C4 -0.8(5) . . . . ? C1 C2 C3 C4 179.6(4) . . . . ? C2 C3 C4 C5 0.4(7) . . . . ? C3 C4 C5 C6 -0.8(7) . . . . ? C4 C5 C6 C7 1.5(7) . . . . ? C3 C2 C7 C6 1.4(5) . . . . ? C1 C2 C7 C6 -178.9(3) . . . . ? C3 C2 C7 C8 179.8(3) . . . . ? C1 C2 C7 C8 -0.5(5) . . . . ? C5 C6 C7 C2 -1.8(6) . . . . ? C5 C6 C7 C8 179.9(4) . . . . ? C2 C7 C8 C9 0.7(5) . . . . ? C6 C7 C8 C9 179.1(4) . . . . ? C7 C8 C9 C10 -0.9(6) . . . . ? C2 C1 C10 C9 -0.6(5) . . . . ? C2 C1 C10 C11 -178.1(3) . . . . ? C8 C9 C10 C1 0.8(6) . . . . ? C8 C9 C10 C11 178.4(4) . . . . ? C1 C10 C11 C12 95.2(5) . . . . ? C9 C10 C11 C12 -82.3(5) . . . . ? C10 C11 C12 C13 -171.2(4) . . . . ? C14 O2 C13 O1 -1.2(6) . . . . ? C14 O2 C13 C12 -179.4(3) . . . . ? C11 C12 C13 O1 4.8(6) . . . . ? C11 C12 C13 O2 -177.0(3) . . . . ? C13 O2 C14 C19 69.6(5) . . . . ? C13 O2 C14 C15 -115.8(4) . . . . ? C19 C14 C15 C16 -0.3(6) . . . . ? O2 C14 C15 C16 -175.0(4) . . . . ? C14 C15 C16 C17 0.0(6) . . . . ? C15 C16 C17 C18 0.4(6) . . . . ? C16 C17 C18 C19 -0.4(7) . . . . ? C15 C14 C19 C18 0.3(6) . . . . ? O2 C14 C19 C18 174.7(4) . . . . ? C17 C18 C19 C14 0.1(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.40 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.180 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.039