# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 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_ax0446 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H14 O3' _chemical_formula_weight 290.30 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)/c 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 12.5264(3) _cell_length_b 10.3959(2) _cell_length_c 10.7767(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.142(1) _cell_angle_gamma 90.00 _cell_volume 1401.27(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9873 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 28.88 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.924 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS (Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'curved graphite' _diffrn_measurement_device_type 'Bruker Kappa APEX II Duo' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30250 _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_sigmaI/netI 0.0122 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3473 _reflns_number_gt 3080 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2011)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0477P)^2^+0.4833P] 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 3473 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0961 _refine_ls_wR_factor_gt 0.0914 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.001 _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 0.37885(8) 0.18172(10) 0.89993(9) 0.0222(2) Uani 1 1 d . . . H1A H 0.4469 0.2140 0.8692 0.027 Uiso 1 1 calc R . . H1B H 0.3834 0.0867 0.9044 0.027 Uiso 1 1 calc R . . C2 C 0.36524(8) 0.23468(9) 1.02922(9) 0.01848(19) Uani 1 1 d . . . H2 H 0.3078 0.1855 1.0693 0.022 Uiso 1 1 calc R . . C3 C 0.46840(8) 0.22165(9) 1.10670(9) 0.0195(2) Uani 1 1 d . . . C4 C 0.55140(8) 0.30951(10) 1.09655(10) 0.0249(2) Uani 1 1 d . . . H4 H 0.5428 0.3806 1.0415 0.030 Uiso 1 1 calc R . . C5 C 0.64680(9) 0.29316(11) 1.16699(11) 0.0300(2) Uani 1 1 d . . . H5 H 0.7030 0.3538 1.1608 0.036 Uiso 1 1 calc R . . C6 C 0.66023(9) 0.18852(11) 1.24640(11) 0.0291(2) Uani 1 1 d . . . H6 H 0.7254 0.1777 1.2946 0.035 Uiso 1 1 calc R . . C7 C 0.57863(9) 0.10005(10) 1.25522(10) 0.0270(2) Uani 1 1 d . . . H7 H 0.5880 0.0279 1.3088 0.032 Uiso 1 1 calc R . . C8 C 0.48272(8) 0.11657(10) 1.18564(10) 0.0233(2) Uani 1 1 d . . . H8 H 0.4267 0.0557 1.1921 0.028 Uiso 1 1 calc R . . C9 C 0.19226(8) 0.20379(10) 0.85892(9) 0.0202(2) Uani 1 1 d . . . C10 C 0.12453(8) 0.11162(10) 0.81085(9) 0.0222(2) Uani 1 1 d . . . H10 H 0.1486 0.0525 0.7512 0.027 Uiso 1 1 calc R . . C11 C 0.01830(8) 0.10368(10) 0.84950(9) 0.0218(2) Uani 1 1 d . . . C12 C -0.05410(9) 0.00901(11) 0.80143(10) 0.0273(2) Uani 1 1 d . . . H12 H -0.0318 -0.0509 0.7415 0.033 Uiso 1 1 calc R . . C13 C -0.15589(9) 0.00357(11) 0.84099(11) 0.0299(2) Uani 1 1 d . . . H13 H -0.2039 -0.0600 0.8079 0.036 Uiso 1 1 calc R . . C14 C -0.19037(9) 0.09099(12) 0.92999(11) 0.0300(2) Uani 1 1 d . . . H14 H -0.2611 0.0854 0.9571 0.036 Uiso 1 1 calc R . . C15 C -0.12267(8) 0.18396(11) 0.97773(10) 0.0262(2) Uani 1 1 d . . . H15 H -0.1468 0.2428 1.0376 0.031 Uiso 1 1 calc R . . C16 C -0.01672(8) 0.19302(10) 0.93843(9) 0.0213(2) Uani 1 1 d . . . C17 C 0.05517(8) 0.28870(9) 0.98517(9) 0.0214(2) Uani 1 1 d . . . H17 H 0.0318 0.3502 1.0430 0.026 Uiso 1 1 calc R . . C18 C 0.15825(8) 0.29383(9) 0.94797(9) 0.0196(2) Uani 1 1 d . . . C19 C 0.23087(8) 0.39808(9) 0.99728(9) 0.0209(2) Uani 1 1 d . . . O1 O 0.29262(6) 0.21715(8) 0.81348(6) 0.02386(17) Uani 1 1 d . . . O2 O 0.33554(6) 0.36948(7) 1.02129(7) 0.02147(16) Uani 1 1 d . . . O3 O 0.20085(6) 0.50587(7) 1.01660(8) 0.02970(19) 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 0.0220(5) 0.0264(5) 0.0184(4) -0.0022(4) 0.0012(4) 0.0005(4) C2 0.0214(4) 0.0155(4) 0.0185(4) 0.0005(3) 0.0011(3) -0.0004(3) C3 0.0213(4) 0.0208(5) 0.0165(4) -0.0025(3) 0.0018(3) 0.0017(4) C4 0.0244(5) 0.0256(5) 0.0248(5) 0.0015(4) 0.0013(4) -0.0016(4) C5 0.0233(5) 0.0313(6) 0.0349(6) -0.0040(5) -0.0011(4) -0.0027(4) C6 0.0258(5) 0.0314(6) 0.0292(5) -0.0078(4) -0.0063(4) 0.0067(4) C7 0.0342(6) 0.0231(5) 0.0231(5) -0.0018(4) -0.0027(4) 0.0079(4) C8 0.0268(5) 0.0203(5) 0.0227(5) -0.0009(4) 0.0011(4) 0.0014(4) C9 0.0215(5) 0.0228(5) 0.0162(4) 0.0017(4) 0.0001(3) -0.0004(4) C10 0.0263(5) 0.0231(5) 0.0170(4) -0.0025(4) -0.0012(4) 0.0003(4) C11 0.0235(5) 0.0213(5) 0.0200(4) 0.0027(4) -0.0040(4) -0.0008(4) C12 0.0297(5) 0.0255(5) 0.0259(5) -0.0004(4) -0.0050(4) -0.0039(4) C13 0.0282(5) 0.0284(6) 0.0322(6) 0.0055(4) -0.0081(4) -0.0072(4) C14 0.0209(5) 0.0333(6) 0.0355(6) 0.0089(5) -0.0025(4) -0.0018(4) C15 0.0220(5) 0.0270(5) 0.0295(5) 0.0043(4) -0.0002(4) 0.0032(4) C16 0.0209(5) 0.0209(5) 0.0216(5) 0.0044(4) -0.0025(4) 0.0013(4) C17 0.0235(5) 0.0194(5) 0.0210(5) 0.0005(4) -0.0006(4) 0.0031(4) C18 0.0226(5) 0.0173(4) 0.0184(4) 0.0014(3) -0.0022(3) 0.0001(4) C19 0.0245(5) 0.0186(4) 0.0196(4) 0.0014(4) -0.0001(4) -0.0009(4) O1 0.0222(4) 0.0338(4) 0.0157(3) -0.0001(3) 0.0017(3) -0.0026(3) O2 0.0230(3) 0.0160(3) 0.0249(4) -0.0002(3) -0.0023(3) -0.0008(3) O3 0.0316(4) 0.0178(4) 0.0393(5) -0.0020(3) -0.0022(3) 0.0021(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 C1 O1 1.4353(12) . ? C1 C2 1.5165(13) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 O2 1.4512(11) . ? C2 C3 1.5057(13) . ? C2 H2 1.0000 . ? C3 C8 1.3902(14) . ? C3 C4 1.3927(14) . ? C4 C5 1.3906(15) . ? C4 H4 0.9500 . ? C5 C6 1.3886(17) . ? C5 H5 0.9500 . ? C6 C7 1.3821(17) . ? C6 H6 0.9500 . ? C7 C8 1.3915(15) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.3631(14) . ? C9 O1 1.3809(12) . ? C9 C18 1.4226(14) . ? C10 C11 1.4183(14) . ? C10 H10 0.9500 . ? C11 C12 1.4170(14) . ? C11 C16 1.4212(15) . ? C12 C13 1.3676(16) . ? C12 H12 0.9500 . ? C13 C14 1.4064(18) . ? C13 H13 0.9500 . ? C14 C15 1.3675(16) . ? C14 H14 0.9500 . ? C15 C16 1.4182(14) . ? C15 H15 0.9500 . ? C16 C17 1.4157(14) . ? C17 C18 1.3738(14) . ? C17 H17 0.9500 . ? C18 C19 1.4938(13) . ? C19 O3 1.2037(13) . ? C19 O2 1.3555(12) . ? 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 C2 112.62(8) . . ? O1 C1 H1A 109.1 . . ? C2 C1 H1A 109.1 . . ? O1 C1 H1B 109.1 . . ? C2 C1 H1B 109.1 . . ? H1A C1 H1B 107.8 . . ? O2 C2 C3 109.21(8) . . ? O2 C2 C1 109.75(8) . . ? C3 C2 C1 109.91(8) . . ? O2 C2 H2 109.3 . . ? C3 C2 H2 109.3 . . ? C1 C2 H2 109.3 . . ? C8 C3 C4 119.44(9) . . ? C8 C3 C2 119.21(9) . . ? C4 C3 C2 121.28(9) . . ? C5 C4 C3 119.99(10) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C6 C5 C4 120.24(11) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C7 C6 C5 119.91(10) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C8 120.05(10) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C3 C8 C7 120.36(10) . . ? C3 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C10 C9 O1 119.72(9) . . ? C10 C9 C18 121.04(9) . . ? O1 C9 C18 119.03(9) . . ? C9 C10 C11 120.25(9) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C12 C11 C10 121.67(10) . . ? C12 C11 C16 119.04(10) . . ? C10 C11 C16 119.29(9) . . ? C13 C12 C11 120.25(11) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 120.81(10) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C15 C14 C13 120.40(10) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 120.38(10) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C17 C16 C15 121.86(10) . . ? C17 C16 C11 119.03(9) . . ? C15 C16 C11 119.11(9) . . ? C18 C17 C16 120.88(9) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C17 C18 C9 119.49(9) . . ? C17 C18 C19 119.22(9) . . ? C9 C18 C19 121.22(9) . . ? O3 C19 O2 118.64(9) . . ? O3 C19 C18 123.16(9) . . ? O2 C19 C18 118.20(8) . . ? C9 O1 C1 114.29(7) . . ? C19 O2 C2 117.72(7) . . ? 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 O2 -46.56(11) . . . . ? O1 C1 C2 C3 -166.67(8) . . . . ? O2 C2 C3 C8 143.01(9) . . . . ? C1 C2 C3 C8 -96.54(11) . . . . ? O2 C2 C3 C4 -39.96(12) . . . . ? C1 C2 C3 C4 80.48(12) . . . . ? C8 C3 C4 C5 -1.33(15) . . . . ? C2 C3 C4 C5 -178.35(9) . . . . ? C3 C4 C5 C6 0.83(17) . . . . ? C4 C5 C6 C7 0.19(17) . . . . ? C5 C6 C7 C8 -0.71(17) . . . . ? C4 C3 C8 C7 0.82(15) . . . . ? C2 C3 C8 C7 177.90(9) . . . . ? C6 C7 C8 C3 0.20(16) . . . . ? O1 C9 C10 C11 -174.87(9) . . . . ? C18 C9 C10 C11 -0.22(15) . . . . ? C9 C10 C11 C12 -179.96(10) . . . . ? C9 C10 C11 C16 0.21(15) . . . . ? C10 C11 C12 C13 179.73(10) . . . . ? C16 C11 C12 C13 -0.44(15) . . . . ? C11 C12 C13 C14 -0.26(16) . . . . ? C12 C13 C14 C15 0.61(17) . . . . ? C13 C14 C15 C16 -0.26(16) . . . . ? C14 C15 C16 C17 179.48(10) . . . . ? C14 C15 C16 C11 -0.43(15) . . . . ? C12 C11 C16 C17 -179.14(9) . . . . ? C10 C11 C16 C17 0.69(14) . . . . ? C12 C11 C16 C15 0.78(14) . . . . ? C10 C11 C16 C15 -179.39(9) . . . . ? C15 C16 C17 C18 178.47(9) . . . . ? C11 C16 C17 C18 -1.62(14) . . . . ? C16 C17 C18 C9 1.62(14) . . . . ? C16 C17 C18 C19 178.63(9) . . . . ? C10 C9 C18 C17 -0.69(14) . . . . ? O1 C9 C18 C17 174.00(8) . . . . ? C10 C9 C18 C19 -177.65(9) . . . . ? O1 C9 C18 C19 -2.96(14) . . . . ? C17 C18 C19 O3 -36.30(15) . . . . ? C9 C18 C19 O3 140.66(11) . . . . ? C17 C18 C19 O2 143.69(9) . . . . ? C9 C18 C19 O2 -39.34(13) . . . . ? C10 C9 O1 C1 -111.72(10) . . . . ? C18 C9 O1 C1 73.52(11) . . . . ? C2 C1 O1 C9 -44.71(11) . . . . ? O3 C19 O2 C2 164.12(9) . . . . ? C18 C19 O2 C2 -15.87(12) . . . . ? C3 C2 O2 C19 -156.12(8) . . . . ? C1 C2 O2 C19 83.34(10) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.342 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 968227'