# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics # This journal is © The Owner Societies 2012 ####################################################################### # # 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_9ac_t135_x15 _database_code_depnum_ccdc_archive 'CCDC 863813' #TrackingRef '9143_web_deposit_cif_file_0_ReneMore_1327063131.135k.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H10 O2' _chemical_formula_sum 'C15 H10 O2' _chemical_formula_weight 222.23 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 3.8340(8) _cell_length_b 9.2980(19) _cell_length_c 28.774(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.15(3) _cell_angle_gamma 90.00 _cell_volume 1025.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 135(2) _cell_measurement_reflns_used 2150 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 28.47 _exptl_crystal_description plate _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS (Bruker, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 135(2) _diffrn_radiation_wavelength 0.60000 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'non-commercial mar CCD' _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 10216 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.19 _diffrn_reflns_theta_max 22.95 _reflns_number_total 2301 _reflns_number_gt 1842 _reflns_threshold_expression I>2\s(I) _computing_data_collection Online _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics 'XP and MERCURY' _computing_publication_material 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^)+(0.0512P)^2^+0.3910P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.073(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2301 _refine_ls_number_parameters 159 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1122 _refine_ls_wR_factor_gt 0.1036 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 C9 C 0.3695(3) 0.19884(15) 0.09793(5) 0.0247(3) Uani 1 1 d . . . O2 O 0.2767(3) 0.15952(11) 0.01797(4) 0.0307(3) Uani 1 1 d . . . C12 C 0.2262(3) 0.13526(14) 0.13802(5) 0.0246(3) Uani 1 1 d . . . C13 C 0.3813(3) 0.43353(15) 0.13626(5) 0.0264(3) Uani 1 1 d . . . C11 C 0.4561(3) 0.34632(14) 0.09660(5) 0.0247(3) Uani 1 1 d . . . C5 C -0.0020(4) 0.16350(17) 0.21752(5) 0.0312(3) Uani 1 1 d . . . H5A H -0.0518 0.2230 0.2435 0.037 Uiso 1 1 calc R . . C14 C 0.1512(3) 0.22562(15) 0.17717(5) 0.0263(3) Uani 1 1 d . . . O1 O 0.5907(3) -0.00384(10) 0.05633(4) 0.0311(3) Uani 1 1 d . . . C1 C 0.6266(4) 0.41303(15) 0.05820(5) 0.0280(3) Uani 1 1 d . . . H1A H 0.6858 0.3569 0.0318 0.034 Uiso 1 1 calc R . . C10 C 0.2259(4) 0.37159(15) 0.17493(5) 0.0275(3) Uani 1 1 d . . . H10A H 0.1689 0.4310 0.2007 0.033 Uiso 1 1 calc R . . C8 C 0.1400(4) -0.01374(15) 0.14174(5) 0.0279(3) Uani 1 1 d . . . H8A H 0.1851 -0.0761 0.1163 0.033 Uiso 1 1 calc R . . C4 C 0.4670(4) 0.58283(15) 0.13515(6) 0.0306(3) Uani 1 1 d . . . H4A H 0.4135 0.6416 0.1612 0.037 Uiso 1 1 calc R . . C7 C -0.0050(4) -0.06775(16) 0.18095(5) 0.0305(3) Uani 1 1 d . . . H7A H -0.0588 -0.1674 0.1826 0.037 Uiso 1 1 calc R . . C2 C 0.7056(4) 0.55560(16) 0.05883(6) 0.0310(3) Uani 1 1 d . . . H2A H 0.8181 0.5977 0.0328 0.037 Uiso 1 1 calc R . . C6 C -0.0778(4) 0.02186(17) 0.21955(6) 0.0327(4) Uani 1 1 d . . . H6A H -0.1797 -0.0176 0.2468 0.039 Uiso 1 1 calc R . . C15 C 0.4243(4) 0.10901(14) 0.05584(5) 0.0250(3) Uani 1 1 d . . . C3 C 0.6231(4) 0.64215(15) 0.09766(6) 0.0317(4) Uani 1 1 d . . . H3A H 0.6771 0.7419 0.0974 0.038 Uiso 1 1 calc R . . H9 H 0.333(6) 0.096(3) -0.0080(9) 0.074(7) Uiso 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 C9 0.0235(6) 0.0246(7) 0.0260(7) -0.0005(5) -0.0009(5) 0.0021(5) O2 0.0405(6) 0.0279(5) 0.0236(6) -0.0012(4) -0.0030(4) 0.0059(4) C12 0.0228(6) 0.0253(7) 0.0258(8) 0.0012(5) -0.0023(5) 0.0016(5) C13 0.0240(7) 0.0259(7) 0.0292(8) -0.0019(5) -0.0030(5) 0.0022(5) C11 0.0231(6) 0.0236(6) 0.0275(8) 0.0001(5) -0.0027(5) 0.0017(5) C5 0.0309(7) 0.0374(8) 0.0253(8) 0.0000(6) 0.0009(6) 0.0034(6) C14 0.0235(7) 0.0298(7) 0.0256(7) 0.0001(6) -0.0015(5) 0.0029(5) O1 0.0405(6) 0.0244(5) 0.0283(6) -0.0015(4) -0.0005(4) 0.0070(4) C1 0.0286(7) 0.0264(7) 0.0290(8) 0.0010(6) -0.0010(6) 0.0005(5) C10 0.0271(7) 0.0288(7) 0.0267(8) -0.0047(6) -0.0011(5) 0.0029(5) C8 0.0269(7) 0.0266(7) 0.0302(8) 0.0011(6) -0.0006(6) 0.0006(5) C4 0.0307(7) 0.0244(7) 0.0366(9) -0.0048(6) -0.0027(6) 0.0020(6) C7 0.0290(7) 0.0281(7) 0.0345(9) 0.0057(6) -0.0006(6) -0.0022(6) C2 0.0293(7) 0.0284(7) 0.0353(9) 0.0061(6) -0.0019(6) -0.0017(6) C6 0.0294(7) 0.0393(8) 0.0294(8) 0.0074(6) 0.0015(6) -0.0001(6) C15 0.0273(7) 0.0221(6) 0.0257(7) 0.0020(5) 0.0005(5) -0.0015(5) C3 0.0306(7) 0.0223(7) 0.0422(9) 0.0021(6) -0.0059(6) -0.0010(5) _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 C9 C12 1.409(2) . ? C9 C11 1.4114(19) . ? C9 C15 1.487(2) . ? O2 C15 1.3132(17) . ? O2 H9 0.98(3) . ? C12 C8 1.4283(19) . ? C12 C14 1.435(2) . ? C13 C10 1.389(2) . ? C13 C4 1.427(2) . ? C13 C11 1.430(2) . ? C11 C1 1.427(2) . ? C5 C6 1.350(2) . ? C5 C14 1.425(2) . ? C5 H5A 0.9500 . ? C14 C10 1.389(2) . ? O1 C15 1.2280(16) . ? C1 C2 1.360(2) . ? C1 H1A 0.9500 . ? C10 H10A 0.9500 . ? C8 C7 1.356(2) . ? C8 H8A 0.9500 . ? C4 C3 1.353(2) . ? C4 H4A 0.9500 . ? C7 C6 1.417(2) . ? C7 H7A 0.9500 . ? C2 C3 1.413(2) . ? C2 H2A 0.9500 . ? C6 H6A 0.9500 . ? C3 H3A 0.9500 . ? 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 C12 C9 C11 121.47(13) . . ? C12 C9 C15 119.18(12) . . ? C11 C9 C15 119.34(12) . . ? C15 O2 H9 108.9(14) . . ? C9 C12 C8 124.00(13) . . ? C9 C12 C14 118.45(12) . . ? C8 C12 C14 117.52(13) . . ? C10 C13 C4 121.38(13) . . ? C10 C13 C11 119.46(13) . . ? C4 C13 C11 119.16(13) . . ? C9 C11 C1 123.47(13) . . ? C9 C11 C13 118.80(13) . . ? C1 C11 C13 117.70(12) . . ? C6 C5 C14 121.33(14) . . ? C6 C5 H5A 119.3 . . ? C14 C5 H5A 119.3 . . ? C10 C14 C5 121.30(14) . . ? C10 C14 C12 119.60(13) . . ? C5 C14 C12 119.09(13) . . ? C2 C1 C11 121.05(14) . . ? C2 C1 H1A 119.5 . . ? C11 C1 H1A 119.5 . . ? C13 C10 C14 122.11(13) . . ? C13 C10 H10A 118.9 . . ? C14 C10 H10A 118.9 . . ? C7 C8 C12 121.14(14) . . ? C7 C8 H8A 119.4 . . ? C12 C8 H8A 119.4 . . ? C3 C4 C13 121.12(14) . . ? C3 C4 H4A 119.4 . . ? C13 C4 H4A 119.4 . . ? C8 C7 C6 121.11(14) . . ? C8 C7 H7A 119.4 . . ? C6 C7 H7A 119.4 . . ? C1 C2 C3 121.01(15) . . ? C1 C2 H2A 119.5 . . ? C3 C2 H2A 119.5 . . ? C5 C6 C7 119.80(14) . . ? C5 C6 H6A 120.1 . . ? C7 C6 H6A 120.1 . . ? O1 C15 O2 122.53(13) . . ? O1 C15 C9 123.04(13) . . ? O2 C15 C9 114.43(12) . . ? C4 C3 C2 119.92(13) . . ? C4 C3 H3A 120.0 . . ? C2 C3 H3A 120.0 . . ? 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 C11 C9 C12 C8 -178.70(13) . . . . ? C15 C9 C12 C8 2.5(2) . . . . ? C11 C9 C12 C14 3.34(19) . . . . ? C15 C9 C12 C14 -175.48(12) . . . . ? C12 C9 C11 C1 174.92(13) . . . . ? C15 C9 C11 C1 -6.3(2) . . . . ? C12 C9 C11 C13 -2.8(2) . . . . ? C15 C9 C11 C13 176.00(12) . . . . ? C10 C13 C11 C9 -0.1(2) . . . . ? C4 C13 C11 C9 -179.80(12) . . . . ? C10 C13 C11 C1 -177.93(12) . . . . ? C4 C13 C11 C1 2.33(19) . . . . ? C6 C5 C14 C10 179.35(13) . . . . ? C6 C5 C14 C12 -0.1(2) . . . . ? C9 C12 C14 C10 -1.01(19) . . . . ? C8 C12 C14 C10 -179.11(12) . . . . ? C9 C12 C14 C5 178.41(12) . . . . ? C8 C12 C14 C5 0.32(19) . . . . ? C9 C11 C1 C2 -179.67(13) . . . . ? C13 C11 C1 C2 -1.9(2) . . . . ? C4 C13 C10 C14 -177.87(13) . . . . ? C11 C13 C10 C14 2.4(2) . . . . ? C5 C14 C10 C13 178.73(13) . . . . ? C12 C14 C10 C13 -1.9(2) . . . . ? C9 C12 C8 C7 -178.43(13) . . . . ? C14 C12 C8 C7 -0.4(2) . . . . ? C10 C13 C4 C3 179.01(13) . . . . ? C11 C13 C4 C3 -1.3(2) . . . . ? C12 C8 C7 C6 0.3(2) . . . . ? C11 C1 C2 C3 0.3(2) . . . . ? C14 C5 C6 C7 -0.1(2) . . . . ? C8 C7 C6 C5 0.0(2) . . . . ? C12 C9 C15 O1 -54.02(19) . . . . ? C11 C9 C15 O1 127.13(15) . . . . ? C12 C9 C15 O2 125.30(14) . . . . ? C11 C9 C15 O2 -53.54(17) . . . . ? C13 C4 C3 C2 -0.4(2) . . . . ? C1 C2 C3 C4 0.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 22.95 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.277 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.048