data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H16 O' _chemical_formula_weight 296.35 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 9.9052(2) _cell_length_b 10.4099(3) _cell_length_c 15.6229(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.067(2) _cell_angle_gamma 90.00 _cell_volume 1586.11(7) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 4178 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 27.28 _exptl_crystal_description rectanguler _exptl_crystal_colour yellow _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8721 _exptl_absorpt_correction_T_max 0.9139 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12878 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3635 _reflns_number_gt 2640 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0754P)^2^+0.2796P] 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 0.0046(14) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3635 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0697 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1502 _refine_ls_wR_factor_gt 0.1362 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 1.14541(11) 0.87162(12) 0.13860(9) 0.0661(4) Uani 1 1 d . . . C1 C 0.9614(2) 1.19533(19) 0.32099(12) 0.0690(5) Uani 1 1 d . . . H1 H 0.9482 1.2577 0.3613 0.083 Uiso 1 1 calc R . . C2 C 0.85857(18) 1.10969(17) 0.29139(10) 0.0557(4) Uani 1 1 d . . . H2 H 0.7759 1.1139 0.3117 0.067 Uiso 1 1 calc R . . C3 C 0.87804(14) 1.01752(15) 0.23152(9) 0.0442(4) Uani 1 1 d . . . H3 H 0.8076 0.9605 0.2109 0.053 Uiso 1 1 calc R . . C4 C 1.00150(13) 1.00878(14) 0.20153(9) 0.0404(3) Uani 1 1 d . . . C5 C 1.02847(14) 0.90491(14) 0.14150(10) 0.0440(3) Uani 1 1 d . . . C6 C 0.90896(14) 0.84389(14) 0.08352(9) 0.0420(3) Uani 1 1 d . . . C7 C 0.89604(15) 0.70592(14) 0.07491(9) 0.0423(3) Uani 1 1 d . . . C8 C 0.78427(16) 0.65389(15) 0.01611(9) 0.0446(4) Uani 1 1 d . . . C9 C 0.76921(19) 0.51902(16) 0.01260(11) 0.0549(4) Uani 1 1 d . . . H9 H 0.6962 0.4840 -0.0259 0.066 Uiso 1 1 calc R . . C10 C 0.8578(2) 0.43761(16) 0.06361(11) 0.0582(5) Uani 1 1 d . . . C11 C 0.8377(3) 0.29438(16) 0.05977(14) 0.0782(6) Uani 1 1 d . . . H11A H 0.7635 0.2735 0.0136 0.117 Uiso 1 1 calc R . . H11B H 0.8165 0.2645 0.1140 0.117 Uiso 1 1 calc R . . H11C H 0.9202 0.2537 0.0492 0.117 Uiso 1 1 calc R . . C12 C 0.98692(17) 0.62169(15) 0.12629(10) 0.0512(4) Uani 1 1 d . . . H12 H 1.0613 0.6547 0.1646 0.061 Uiso 1 1 calc R . . C13 C 0.96724(19) 0.49017(17) 0.12061(11) 0.0588(5) Uani 1 1 d . . . H13 H 1.0283 0.4361 0.1555 0.071 Uiso 1 1 calc R . . C14 C 0.68751(16) 0.73906(15) -0.03740(9) 0.0457(4) Uani 1 1 d . . . C15 C 0.57814(19) 0.69520(18) -0.09947(11) 0.0635(5) Uani 1 1 d . . . H15 H 0.5653 0.6074 -0.1082 0.076 Uiso 1 1 calc R . . C16 C 0.4896(2) 0.7795(2) -0.14757(13) 0.0722(6) Uani 1 1 d . . . H16 H 0.4177 0.7479 -0.1885 0.087 Uiso 1 1 calc R . . C17 C 0.50508(18) 0.9108(2) -0.13640(11) 0.0645(5) Uani 1 1 d . . . H17 H 0.4438 0.9670 -0.1692 0.077 Uiso 1 1 calc R . . C18 C 0.61186(17) 0.95724(17) -0.07641(10) 0.0552(4) Uani 1 1 d . . . H18 H 0.6230 1.0455 -0.0688 0.066 Uiso 1 1 calc R . . C19 C 0.70399(15) 0.87337(15) -0.02661(9) 0.0450(4) Uani 1 1 d . . . C20 C 0.81489(15) 0.92252(14) 0.03510(10) 0.0451(4) Uani 1 1 d . . . H20 H 0.8235 1.0109 0.0427 0.054 Uiso 1 1 calc R . . C21 C 1.10521(16) 1.09567(17) 0.23237(11) 0.0570(4) Uani 1 1 d . . . H21 H 1.1889 1.0907 0.2134 0.068 Uiso 1 1 calc R . . C22 C 1.0840(2) 1.18919(19) 0.29115(13) 0.0723(6) Uani 1 1 d . . . H22 H 1.1529 1.2484 0.3107 0.087 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 0.0420(6) 0.0623(8) 0.0922(9) -0.0150(7) 0.0071(6) 0.0089(5) C1 0.0788(13) 0.0664(12) 0.0599(11) -0.0226(9) 0.0074(9) -0.0015(10) C2 0.0547(9) 0.0647(11) 0.0485(9) -0.0056(8) 0.0107(7) 0.0041(8) C3 0.0403(7) 0.0462(8) 0.0436(8) -0.0001(7) 0.0003(6) -0.0031(6) C4 0.0380(7) 0.0383(7) 0.0420(7) 0.0007(6) -0.0009(6) -0.0007(6) C5 0.0394(8) 0.0405(8) 0.0509(8) 0.0023(7) 0.0046(6) 0.0011(6) C6 0.0427(8) 0.0395(8) 0.0441(8) -0.0036(6) 0.0084(6) -0.0002(6) C7 0.0480(8) 0.0390(8) 0.0418(7) -0.0012(6) 0.0132(6) 0.0021(6) C8 0.0555(9) 0.0428(8) 0.0374(7) -0.0064(6) 0.0137(6) -0.0055(7) C9 0.0761(11) 0.0444(9) 0.0462(8) -0.0044(7) 0.0160(8) -0.0043(8) C10 0.0870(13) 0.0386(9) 0.0557(10) -0.0013(8) 0.0306(9) 0.0012(8) C11 0.1201(17) 0.0402(10) 0.0825(13) 0.0003(9) 0.0404(13) -0.0012(10) C12 0.0533(9) 0.0481(9) 0.0522(9) 0.0038(8) 0.0098(7) 0.0085(7) C13 0.0715(11) 0.0485(9) 0.0594(10) 0.0087(8) 0.0197(9) 0.0147(8) C14 0.0555(9) 0.0434(8) 0.0390(7) -0.0044(7) 0.0102(6) -0.0055(7) C15 0.0714(11) 0.0576(10) 0.0563(10) -0.0107(9) -0.0029(9) -0.0088(9) C16 0.0672(12) 0.0797(14) 0.0608(11) -0.0108(10) -0.0136(9) -0.0065(10) C17 0.0594(10) 0.0736(12) 0.0545(10) 0.0005(9) -0.0074(8) 0.0103(9) C18 0.0560(9) 0.0532(10) 0.0535(9) 0.0019(8) 0.0019(7) 0.0054(8) C19 0.0470(8) 0.0464(8) 0.0410(7) -0.0012(7) 0.0063(6) 0.0001(6) C20 0.0475(8) 0.0360(7) 0.0499(8) -0.0044(7) 0.0032(6) -0.0004(6) C21 0.0434(8) 0.0592(10) 0.0666(10) -0.0111(9) 0.0045(7) -0.0099(7) C22 0.0680(12) 0.0670(12) 0.0780(13) -0.0252(10) 0.0018(10) -0.0218(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 O1 C5 1.2175(17) . ? C1 C2 1.372(2) . ? C1 C22 1.376(3) . ? C1 H1 0.9300 . ? C2 C3 1.377(2) . ? C2 H2 0.9300 . ? C3 C4 1.3870(19) . ? C3 H3 0.9300 . ? C4 C21 1.390(2) . ? C4 C5 1.486(2) . ? C5 C6 1.5001(19) . ? C6 C20 1.365(2) . ? C6 C7 1.446(2) . ? C7 C12 1.404(2) . ? C7 C8 1.417(2) . ? C8 C9 1.412(2) . ? C8 C14 1.457(2) . ? C9 C10 1.370(2) . ? C9 H9 0.9300 . ? C10 C13 1.390(3) . ? C10 C11 1.504(2) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.384(2) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.398(2) . ? C14 C19 1.414(2) . ? C15 C16 1.369(3) . ? C15 H15 0.9300 . ? C16 C17 1.383(3) . ? C16 H16 0.9300 . ? C17 C18 1.373(2) . ? C17 H17 0.9300 . ? C18 C19 1.397(2) . ? C18 H18 0.9300 . ? C19 C20 1.424(2) . ? C20 H20 0.9300 . ? C21 C22 1.379(2) . ? C21 H21 0.9300 . ? C22 H22 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 C2 C1 C22 120.19(17) . . ? C2 C1 H1 119.9 . . ? C22 C1 H1 119.9 . . ? C1 C2 C3 119.87(16) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C2 C3 C4 120.77(14) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C3 C4 C21 118.82(14) . . ? C3 C4 C5 121.83(13) . . ? C21 C4 C5 119.26(13) . . ? O1 C5 C4 120.52(13) . . ? O1 C5 C6 120.83(14) . . ? C4 C5 C6 118.64(12) . . ? C20 C6 C7 120.21(13) . . ? C20 C6 C5 118.08(13) . . ? C7 C6 C5 121.62(13) . . ? C12 C7 C8 118.84(14) . . ? C12 C7 C6 121.98(14) . . ? C8 C7 C6 119.10(13) . . ? C9 C8 C7 118.07(15) . . ? C9 C8 C14 121.89(14) . . ? C7 C8 C14 120.03(13) . . ? C10 C9 C8 122.67(16) . . ? C10 C9 H9 118.7 . . ? C8 C9 H9 118.7 . . ? C9 C10 C13 118.53(15) . . ? C9 C10 C11 121.54(19) . . ? C13 C10 C11 119.93(18) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C7 120.81(16) . . ? C13 C12 H12 119.6 . . ? C7 C12 H12 119.6 . . ? C12 C13 C10 121.08(16) . . ? C12 C13 H13 119.5 . . ? C10 C13 H13 119.5 . . ? C15 C14 C19 117.70(15) . . ? C15 C14 C8 123.46(15) . . ? C19 C14 C8 118.85(13) . . ? C16 C15 C14 121.04(17) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C17 121.21(16) . . ? C15 C16 H16 119.4 . . ? C17 C16 H16 119.4 . . ? C18 C17 C16 119.31(17) . . ? C18 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? C17 C18 C19 120.69(17) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C18 C19 C14 120.06(14) . . ? C18 C19 C20 120.26(14) . . ? C14 C19 C20 119.69(14) . . ? C6 C20 C19 122.05(14) . . ? C6 C20 H20 119.0 . . ? C19 C20 H20 119.0 . . ? C22 C21 C4 120.05(16) . . ? C22 C21 H21 120.0 . . ? C4 C21 H21 120.0 . . ? C1 C22 C21 120.28(17) . . ? C1 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.213 _refine_diff_density_min -0.166 _refine_diff_density_rms 0.038