data_uj _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H14 O' _chemical_formula_weight 294.33 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1784(2) _cell_length_b 10.2343(2) _cell_length_c 10.5109(3) _cell_angle_alpha 98.755(2) _cell_angle_beta 113.273(2) _cell_angle_gamma 114.4400(10) _cell_volume 764.64(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 250 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 27.5 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8737 _exptl_absorpt_correction_T_max 0.9826 _exptl_absorpt_process_details ; 'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL SPACE EXPLORATION, Bruker Analytical X-ray Systems, 1997 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12329 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3462 _reflns_number_gt 2110 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART APEX II (Bruker,2010)' _computing_cell_refinement 'SMART APEX II' _computing_data_reduction 'SAINT (Bruker,2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3v2 for windows (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 2008)' _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^ > 2\s(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^)+(0.0635P)^2^+0.1056P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3462 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0903 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1476 _refine_ls_wR_factor_gt 0.1280 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 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 0.3354(3) 0.1096(3) 0.6076(2) 0.0723(6) Uani 1 1 d . . . H1 H 0.2241 0.0258 0.5862 0.087 Uiso 1 1 calc R . . C2 C 0.3404(3) 0.2388(3) 0.5880(2) 0.0798(6) Uani 1 1 d . . . H2 H 0.2327 0.2429 0.5533 0.096 Uiso 1 1 calc R . . C3 C 0.5056(3) 0.3656(3) 0.6195(2) 0.0776(6) Uani 1 1 d . . . H3 H 0.5080 0.4546 0.6079 0.093 Uiso 1 1 calc R . . C4 C 0.6639(3) 0.3608(2) 0.6672(2) 0.0644(5) Uani 1 1 d . . . H4 H 0.7724 0.4459 0.6858 0.077 Uiso 1 1 calc R . . C5 C 0.6656(2) 0.2283(2) 0.68886(18) 0.0538(4) Uani 1 1 d . . . C6 C 0.4970(2) 0.1001(2) 0.66020(19) 0.0588(5) Uani 1 1 d . . . C7 C 0.4926(3) -0.0326(2) 0.68240(19) 0.0620(5) Uani 1 1 d . . . H7 H 0.3846 -0.1169 0.6656 0.074 Uiso 1 1 calc R . . C8 C 0.6533(3) -0.03222(19) 0.72967(19) 0.0580(5) Uani 1 1 d . . . C9 C 0.8250(2) 0.09251(19) 0.75856(18) 0.0575(5) Uani 1 1 d . . . C10 C 0.8320(2) 0.2238(2) 0.73909(19) 0.0569(5) Uani 1 1 d . . . C11 C 0.9577(2) 0.04046(19) 0.80249(18) 0.0540(4) Uani 1 1 d . . . C12 C 0.8565(3) -0.1081(2) 0.7970(2) 0.0614(5) Uani 1 1 d . . . C13 C 0.9297(3) -0.1990(2) 0.8301(2) 0.0762(6) Uani 1 1 d . . . H13 H 0.8589 -0.2973 0.8267 0.091 Uiso 1 1 calc R . . C14 C 1.1116(4) -0.1394(3) 0.8685(2) 0.0840(7) Uani 1 1 d . . . H14 H 1.1655 -0.1985 0.8912 0.101 Uiso 1 1 calc R . . C15 C 1.2172(3) 0.0078(3) 0.8742(2) 0.0769(6) Uani 1 1 d . . . H15 H 1.3405 0.0457 0.9003 0.092 Uiso 1 1 calc R . . C16 C 1.1413(3) 0.0983(2) 0.8415(2) 0.0645(5) Uani 1 1 d . . . H16 H 1.2126 0.1969 0.8457 0.077 Uiso 1 1 calc R . . C17 C 1.0118(2) 0.35765(19) 0.7716(2) 0.0566(5) Uani 1 1 d . . . C18 C 1.1526(3) 0.4541(2) 0.9176(2) 0.0734(6) Uani 1 1 d . . . H18 H 1.1348 0.4356 0.9958 0.088 Uiso 1 1 calc R . . C19 C 1.3186(3) 0.5771(2) 0.9494(2) 0.0802(6) Uani 1 1 d . . . H19 H 1.4120 0.6407 1.0481 0.096 Uiso 1 1 calc R . . C20 C 1.3450(3) 0.6049(2) 0.8347(3) 0.0744(6) Uani 1 1 d . . . H20 H 1.4568 0.6874 0.8555 0.089 Uiso 1 1 calc R . . C21 C 1.2076(3) 0.5119(2) 0.6901(2) 0.0720(6) Uani 1 1 d . . . H21 H 1.2255 0.5319 0.6124 0.086 Uiso 1 1 calc R . . C22 C 1.0423(3) 0.3882(2) 0.6586(2) 0.0667(5) Uani 1 1 d . . . H22 H 0.9501 0.3247 0.5596 0.080 Uiso 1 1 calc R . . O1 O 0.67404(18) -0.15392(14) 0.75505(14) 0.0701(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 0.0616(12) 0.0787(15) 0.0598(12) 0.0114(11) 0.0316(10) 0.0275(11) C2 0.0734(14) 0.0986(18) 0.0719(14) 0.0253(13) 0.0356(12) 0.0521(14) C3 0.0886(15) 0.0832(15) 0.0732(14) 0.0322(12) 0.0411(12) 0.0538(13) C4 0.0691(12) 0.0617(12) 0.0604(12) 0.0215(10) 0.0334(10) 0.0327(10) C5 0.0573(10) 0.0548(11) 0.0455(10) 0.0147(8) 0.0264(8) 0.0274(9) C6 0.0596(11) 0.0604(11) 0.0453(10) 0.0115(9) 0.0274(9) 0.0245(9) C7 0.0614(11) 0.0508(11) 0.0559(11) 0.0137(9) 0.0323(9) 0.0148(9) C8 0.0678(12) 0.0410(9) 0.0513(11) 0.0149(8) 0.0329(9) 0.0157(9) C9 0.0703(12) 0.0452(10) 0.0453(10) 0.0138(8) 0.0306(9) 0.0210(9) C10 0.0644(11) 0.0484(10) 0.0474(10) 0.0147(8) 0.0283(9) 0.0224(9) C11 0.0666(11) 0.0469(10) 0.0472(10) 0.0180(8) 0.0289(9) 0.0284(9) C12 0.0744(13) 0.0487(10) 0.0527(11) 0.0176(9) 0.0328(10) 0.0255(10) C13 0.1064(17) 0.0528(12) 0.0731(14) 0.0287(11) 0.0458(13) 0.0428(12) C14 0.117(2) 0.0806(16) 0.0761(15) 0.0353(13) 0.0475(14) 0.0690(15) C15 0.0828(14) 0.0824(15) 0.0747(14) 0.0300(12) 0.0400(12) 0.0504(13) C16 0.0718(13) 0.0573(11) 0.0631(12) 0.0232(10) 0.0345(10) 0.0322(10) C17 0.0609(11) 0.0415(9) 0.0584(11) 0.0188(9) 0.0314(9) 0.0186(8) C18 0.0756(13) 0.0559(12) 0.0597(12) 0.0224(10) 0.0323(11) 0.0131(10) C19 0.0670(13) 0.0591(12) 0.0713(14) 0.0201(11) 0.0252(11) 0.0093(10) C20 0.0626(12) 0.0553(12) 0.0967(17) 0.0322(12) 0.0428(12) 0.0206(10) C21 0.0809(14) 0.0669(13) 0.0803(15) 0.0394(12) 0.0523(12) 0.0338(11) C22 0.0677(12) 0.0613(12) 0.0579(12) 0.0216(10) 0.0328(10) 0.0227(10) O1 0.0800(9) 0.0455(7) 0.0718(9) 0.0227(7) 0.0402(7) 0.0206(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.354(3) . ? C1 C6 1.415(3) . ? C2 C3 1.392(3) . ? C3 C4 1.362(3) . ? C4 C5 1.414(2) . ? C5 C6 1.428(2) . ? C5 C10 1.429(2) . ? C6 C7 1.399(3) . ? C7 C8 1.356(3) . ? C8 O1 1.384(2) . ? C8 C9 1.430(2) . ? C9 C10 1.368(2) . ? C9 C11 1.465(3) . ? C10 C17 1.503(2) . ? C11 C16 1.383(3) . ? C11 C12 1.393(2) . ? C12 C13 1.368(3) . ? C12 O1 1.386(2) . ? C13 C14 1.368(3) . ? C14 C15 1.390(3) . ? C15 C16 1.380(3) . ? C17 C22 1.375(2) . ? C17 C18 1.384(3) . ? C18 C19 1.378(3) . ? C19 C20 1.367(3) . ? C20 C21 1.363(3) . ? C21 C22 1.379(2) . ? 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 121.0(2) . . ? C1 C2 C3 120.4(2) . . ? C4 C3 C2 120.7(2) . . ? C3 C4 C5 120.94(19) . . ? C4 C5 C6 118.11(16) . . ? C4 C5 C10 120.79(16) . . ? C6 C5 C10 121.10(16) . . ? C7 C6 C1 121.08(18) . . ? C7 C6 C5 120.21(17) . . ? C1 C6 C5 118.71(18) . . ? C8 C7 C6 116.76(17) . . ? C7 C8 O1 124.75(16) . . ? C7 C8 C9 125.13(17) . . ? O1 C8 C9 110.12(16) . . ? C10 C9 C8 118.77(18) . . ? C10 C9 C11 135.01(17) . . ? C8 C9 C11 106.21(15) . . ? C9 C10 C5 118.03(16) . . ? C9 C10 C17 119.78(17) . . ? C5 C10 C17 122.19(16) . . ? C16 C11 C12 118.29(17) . . ? C16 C11 C9 137.16(16) . . ? C12 C11 C9 104.54(16) . . ? C13 C12 O1 123.52(18) . . ? C13 C12 C11 123.5(2) . . ? O1 C12 C11 113.01(16) . . ? C12 C13 C14 117.2(2) . . ? C13 C14 C15 121.2(2) . . ? C16 C15 C14 120.8(2) . . ? C15 C16 C11 119.06(18) . . ? C22 C17 C18 117.94(17) . . ? C22 C17 C10 121.54(16) . . ? C18 C17 C10 120.53(15) . . ? C19 C18 C17 121.26(18) . . ? C20 C19 C18 119.53(19) . . ? C21 C20 C19 120.16(18) . . ? C20 C21 C22 120.19(18) . . ? C17 C22 C21 120.91(18) . . ? C8 O1 C12 106.12(13) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.322 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.028