# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cu-kb1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H16 O2' _chemical_formula_sum 'C22 H16 O2' _chemical_formula_weight 312.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 '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 7.5080(4) _cell_length_b 9.0339(7) _cell_length_c 12.3483(7) _cell_angle_alpha 82.421(5) _cell_angle_beta 87.073(4) _cell_angle_gamma 65.899(6) _cell_volume 757.85(8) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 3551 _cell_measurement_theta_min 5.4000 _cell_measurement_theta_max 73.4363 _exptl_crystal_description 'needle plate' _exptl_crystal_colour red-brown _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.685 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.81280 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.5081 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4872 _diffrn_reflns_av_R_equivalents 0.0152 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 5.40 _diffrn_reflns_theta_max 73.60 _reflns_number_total 2978 _reflns_number_gt 2709 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXLTL (Sheldrick, 2008)' _computing_publication_material SHELXLTL _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^)+(0.0824P)^2^+0.2469P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2978 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1420 _refine_ls_wR_factor_gt 0.1381 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 0.74578(18) 0.16280(14) 0.44383(9) 0.0336(3) Uani 1 1 d . . . O2 O 0.47550(18) 0.78528(14) 1.04121(9) 0.0329(3) Uani 1 1 d . . . C1 C 0.7483(2) 0.24173(18) 0.51754(12) 0.0243(3) Uani 1 1 d . . . C2 C 0.74148(19) 0.40896(17) 0.49362(11) 0.0219(3) Uani 1 1 d . . . C3 C 0.7398(2) 0.47577(19) 0.38477(12) 0.0259(3) Uani 1 1 d . . . H3 H 0.7337 0.4168 0.3278 0.031 Uiso 1 1 calc R . . C4 C 0.7471(2) 0.6270(2) 0.35920(12) 0.0286(3) Uani 1 1 d . . . H4 H 0.7389 0.6742 0.2852 0.034 Uiso 1 1 calc R . . C5 C 0.7665(2) 0.70959(18) 0.44212(12) 0.0270(3) Uani 1 1 d . . . H5 H 0.7780 0.8109 0.4246 0.032 Uiso 1 1 calc R . . C6 C 0.7690(2) 0.64415(18) 0.55040(12) 0.0233(3) Uani 1 1 d . . . H6 H 0.7868 0.6998 0.6063 0.028 Uiso 1 1 calc R . . C7 C 0.74585(19) 0.49744(17) 0.57918(11) 0.0208(3) Uani 1 1 d . . . C8 C 0.7440(2) 0.42791(17) 0.69332(11) 0.0206(3) Uani 1 1 d . . . C9 C 0.7620(2) 0.26063(17) 0.71305(12) 0.0232(3) Uani 1 1 d . . . H9 H 0.7758 0.2101 0.7864 0.028 Uiso 1 1 calc R . . C10 C 0.7604(2) 0.17205(17) 0.63279(12) 0.0243(3) Uani 1 1 d . . . C11 C 0.7575(2) 0.00643(18) 0.65663(14) 0.0313(4) Uani 1 1 d . . . H11A H 0.7448 -0.0189 0.7355 0.047 Uiso 1 1 calc R . . H11B H 0.8792 -0.0753 0.6311 0.047 Uiso 1 1 calc R . . H11C H 0.6466 0.0050 0.6189 0.047 Uiso 1 1 calc R . . C12 C 0.5494(2) 0.70807(18) 0.96405(12) 0.0240(3) Uani 1 1 d . . . C13 C 0.6994(2) 0.53801(17) 0.98078(11) 0.0222(3) Uani 1 1 d . . . C14 C 0.7682(2) 0.47073(19) 1.08669(12) 0.0278(3) Uani 1 1 d . . . H14 H 0.7099 0.5304 1.1463 0.033 Uiso 1 1 calc R . . C15 C 0.9198(2) 0.3185(2) 1.10590(12) 0.0306(4) Uani 1 1 d . . . H15 H 0.9625 0.2723 1.1785 0.037 Uiso 1 1 calc R . . C16 C 1.0097(2) 0.23309(19) 1.01846(13) 0.0285(3) Uani 1 1 d . . . H16 H 1.1176 0.1304 1.0310 0.034 Uiso 1 1 calc R . . C17 C 0.9417(2) 0.29813(18) 0.91297(12) 0.0240(3) Uani 1 1 d . . . H17 H 1.0055 0.2400 0.8536 0.029 Uiso 1 1 calc R . . C18 C 0.7802(2) 0.44831(17) 0.89217(11) 0.0206(3) Uani 1 1 d . . . C19 C 0.7059(2) 0.52034(17) 0.78119(11) 0.0200(3) Uani 1 1 d . . . C20 C 0.5725(2) 0.69071(17) 0.76692(11) 0.0225(3) Uani 1 1 d . . . H20 H 0.5371 0.7428 0.6945 0.027 Uiso 1 1 calc R . . C21 C 0.4949(2) 0.78064(17) 0.85042(12) 0.0244(3) Uani 1 1 d . . . C22 C 0.3406(3) 0.95139(19) 0.83262(13) 0.0321(4) Uani 1 1 d . . . H22A H 0.3146 0.9845 0.7542 0.048 Uiso 1 1 calc R . . H22B H 0.3857 1.0258 0.8620 0.048 Uiso 1 1 calc R . . H22C H 0.2207 0.9555 0.8701 0.048 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 0.0449(7) 0.0285(6) 0.0274(6) -0.0111(4) -0.0042(5) -0.0122(5) O2 0.0460(7) 0.0268(6) 0.0249(6) -0.0113(4) 0.0098(5) -0.0125(5) C1 0.0210(7) 0.0246(7) 0.0249(7) -0.0086(6) 0.0003(5) -0.0050(5) C2 0.0182(6) 0.0234(7) 0.0214(7) -0.0050(5) 0.0001(5) -0.0051(5) C3 0.0240(7) 0.0321(8) 0.0201(7) -0.0071(6) 0.0009(5) -0.0087(6) C4 0.0288(7) 0.0347(8) 0.0189(7) 0.0013(6) 0.0005(6) -0.0107(6) C5 0.0276(7) 0.0242(7) 0.0270(7) 0.0001(6) 0.0024(6) -0.0095(6) C6 0.0240(7) 0.0226(7) 0.0214(7) -0.0062(5) 0.0023(5) -0.0066(5) C7 0.0189(6) 0.0211(7) 0.0190(7) -0.0046(5) 0.0015(5) -0.0042(5) C8 0.0202(6) 0.0202(7) 0.0195(7) -0.0042(5) 0.0005(5) -0.0058(5) C9 0.0260(7) 0.0199(7) 0.0211(7) -0.0038(5) 0.0008(5) -0.0064(5) C10 0.0243(7) 0.0192(7) 0.0273(7) -0.0053(6) -0.0004(5) -0.0061(5) C11 0.0386(9) 0.0200(7) 0.0352(8) -0.0055(6) -0.0020(7) -0.0108(6) C12 0.0313(8) 0.0218(7) 0.0226(7) -0.0073(5) 0.0058(6) -0.0138(6) C13 0.0283(7) 0.0216(7) 0.0202(7) -0.0039(5) 0.0029(5) -0.0135(6) C14 0.0385(8) 0.0301(8) 0.0177(7) -0.0056(6) 0.0019(6) -0.0164(7) C15 0.0379(9) 0.0334(8) 0.0206(7) 0.0014(6) -0.0058(6) -0.0154(7) C16 0.0288(8) 0.0256(7) 0.0291(8) 0.0003(6) -0.0040(6) -0.0096(6) C17 0.0273(7) 0.0223(7) 0.0224(7) -0.0049(5) 0.0015(5) -0.0097(6) C18 0.0255(7) 0.0198(7) 0.0186(7) -0.0030(5) 0.0010(5) -0.0113(5) C19 0.0228(7) 0.0189(7) 0.0184(6) -0.0042(5) 0.0034(5) -0.0084(5) C20 0.0274(7) 0.0191(7) 0.0195(6) -0.0016(5) 0.0017(5) -0.0085(6) C21 0.0284(7) 0.0182(7) 0.0256(7) -0.0035(5) 0.0045(6) -0.0087(6) C22 0.0395(9) 0.0193(7) 0.0307(8) -0.0051(6) 0.0072(6) -0.0053(6) _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 1.2334(18) . ? O2 C12 1.2278(18) . ? C1 C10 1.470(2) . ? C1 C2 1.481(2) . ? C2 C3 1.397(2) . ? C2 C7 1.4156(19) . ? C3 C4 1.384(2) . ? C3 H3 0.9500 . ? C4 C5 1.390(2) . ? C4 H4 0.9500 . ? C5 C6 1.387(2) . ? C5 H5 0.9500 . ? C6 C7 1.404(2) . ? C6 H6 0.9500 . ? C7 C8 1.4673(19) . ? C8 C19 1.4030(19) . ? C8 C9 1.449(2) . ? C9 C10 1.357(2) . ? C9 H9 0.9500 . ? C10 C11 1.495(2) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C21 1.471(2) . ? C12 C13 1.483(2) . ? C13 C14 1.396(2) . ? C13 C18 1.4094(19) . ? C14 C15 1.381(2) . ? C14 H14 0.9500 . ? C15 C16 1.392(2) . ? C15 H15 0.9500 . ? C16 C17 1.387(2) . ? C16 H16 0.9500 . ? C17 C18 1.405(2) . ? C17 H17 0.9500 . ? C18 C19 1.4694(19) . ? C19 C20 1.4458(19) . ? C20 C21 1.355(2) . ? C20 H20 0.9500 . ? C21 C22 1.499(2) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? 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 O1 C1 C10 120.99(14) . . ? O1 C1 C2 121.53(14) . . ? C10 C1 C2 117.48(12) . . ? C3 C2 C7 120.18(14) . . ? C3 C2 C1 118.95(13) . . ? C7 C2 C1 120.80(13) . . ? C4 C3 C2 120.59(14) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 119.80(14) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 120.02(14) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 121.41(14) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C6 C7 C2 117.58(13) . . ? C6 C7 C8 122.27(13) . . ? C2 C7 C8 119.93(13) . . ? C19 C8 C9 119.43(13) . . ? C19 C8 C7 123.00(13) . . ? C9 C8 C7 117.23(12) . . ? C10 C9 C8 123.81(13) . . ? C10 C9 H9 118.1 . . ? C8 C9 H9 118.1 . . ? C9 C10 C1 120.35(13) . . ? C9 C10 C11 122.35(14) . . ? C1 C10 C11 117.18(13) . . ? 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 . . ? O2 C12 C21 121.55(14) . . ? O2 C12 C13 121.68(14) . . ? C21 C12 C13 116.77(12) . . ? C14 C13 C18 120.11(13) . . ? C14 C13 C12 118.29(13) . . ? C18 C13 C12 121.50(13) . . ? C15 C14 C13 120.81(14) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C14 C15 C16 119.73(14) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C17 C16 C15 119.93(14) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 121.28(13) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C17 C18 C13 117.85(13) . . ? C17 C18 C19 122.37(12) . . ? C13 C18 C19 119.53(13) . . ? C8 C19 C20 119.77(12) . . ? C8 C19 C18 122.87(12) . . ? C20 C19 C18 117.07(12) . . ? C21 C20 C19 124.05(13) . . ? C21 C20 H20 118.0 . . ? C19 C20 H20 118.0 . . ? C20 C21 C12 120.41(13) . . ? C20 C21 C22 122.19(14) . . ? C12 C21 C22 117.23(13) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? 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 O1 C1 C2 C3 -2.6(2) . . . . ? C10 C1 C2 C3 176.84(12) . . . . ? O1 C1 C2 C7 -179.58(13) . . . . ? C10 C1 C2 C7 -0.2(2) . . . . ? C7 C2 C3 C4 1.5(2) . . . . ? C1 C2 C3 C4 -175.50(13) . . . . ? C2 C3 C4 C5 3.4(2) . . . . ? C3 C4 C5 C6 -3.1(2) . . . . ? C4 C5 C6 C7 -2.1(2) . . . . ? C5 C6 C7 C2 6.9(2) . . . . ? C5 C6 C7 C8 -178.69(13) . . . . ? C3 C2 C7 C6 -6.5(2) . . . . ? C1 C2 C7 C6 170.47(12) . . . . ? C3 C2 C7 C8 178.89(12) . . . . ? C1 C2 C7 C8 -4.1(2) . . . . ? C6 C7 C8 C19 19.8(2) . . . . ? C2 C7 C8 C19 -165.83(13) . . . . ? C6 C7 C8 C9 -166.87(13) . . . . ? C2 C7 C8 C9 7.5(2) . . . . ? C19 C8 C9 C10 166.59(14) . . . . ? C7 C8 C9 C10 -7.0(2) . . . . ? C8 C9 C10 C1 2.8(2) . . . . ? C8 C9 C10 C11 -173.18(14) . . . . ? O1 C1 C10 C9 -179.64(14) . . . . ? C2 C1 C10 C9 1.0(2) . . . . ? O1 C1 C10 C11 -3.5(2) . . . . ? C2 C1 C10 C11 177.11(13) . . . . ? O2 C12 C13 C14 -5.3(2) . . . . ? C21 C12 C13 C14 173.97(13) . . . . ? O2 C12 C13 C18 178.33(13) . . . . ? C21 C12 C13 C18 -2.4(2) . . . . ? C18 C13 C14 C15 2.1(2) . . . . ? C12 C13 C14 C15 -174.25(14) . . . . ? C13 C14 C15 C16 2.1(2) . . . . ? C14 C15 C16 C17 -2.6(2) . . . . ? C15 C16 C17 C18 -1.2(2) . . . . ? C16 C17 C18 C13 5.3(2) . . . . ? C16 C17 C18 C19 179.64(13) . . . . ? C14 C13 C18 C17 -5.8(2) . . . . ? C12 C13 C18 C17 170.49(13) . . . . ? C14 C13 C18 C19 179.76(13) . . . . ? C12 C13 C18 C19 -4.0(2) . . . . ? C9 C8 C19 C20 -140.33(14) . . . . ? C7 C8 C19 C20 32.8(2) . . . . ? C9 C8 C19 C18 33.2(2) . . . . ? C7 C8 C19 C18 -153.60(13) . . . . ? C17 C18 C19 C8 21.1(2) . . . . ? C13 C18 C19 C8 -164.66(13) . . . . ? C17 C18 C19 C20 -165.13(13) . . . . ? C13 C18 C19 C20 9.1(2) . . . . ? C8 C19 C20 C21 165.59(14) . . . . ? C18 C19 C20 C21 -8.3(2) . . . . ? C19 C20 C21 C12 2.0(2) . . . . ? C19 C20 C21 C22 -173.14(14) . . . . ? O2 C12 C21 C20 -177.24(14) . . . . ? C13 C12 C21 C20 3.5(2) . . . . ? O2 C12 C21 C22 -1.8(2) . . . . ? C13 C12 C21 C22 178.85(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C20 H20A O1 0.95 2.58 3.3733(18) 141.0 2_666 _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 67.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.400 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 801765'