# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2009 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'C Wilson' 'Alastair Florence' 'Lynne H. Thomas' _publ_contact_author_name 'Chick Wilson' _publ_contact_author_email CHICK@CHEM.GLA.AC.UK _publ_section_title ; Imaging proton behaviour in a short intramolecular hydrogen bond using the combined approach of X-ray and neutron diffraction ; # Attachment 'B908915B_dbm_neutron3.cif' data_dbm100 _database_code_depnum_ccdc_archive 'CCDC 739586' _audit_creation_method SHELXL-97 _chemical_name_systematic ; dibenzoylmethane ; _chemical_name_common dibenzoylmethane _chemical_melting_point ? _chemical_formula_moiety 'C15 O2 H12' _chemical_formula_sum 'C15 H12 O2' _chemical_formula_weight 224.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 6.646 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H -3.739 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 5.803 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 8.6251(5) _cell_length_b 10.6442(8) _cell_length_c 24.3193(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2232.7(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 2.5 _exptl_crystal_size_mid 2.0 _exptl_crystal_size_min 1.5 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 53 _exptl_absorpt_coefficient_mu '1.72, at 1 Angstrom' _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.513 _exptl_absorpt_correction_T_max 0.773 _exptl_absorpt_process_details ; The linear absorption coefficient is wavelength dependent and it is calculated as: mu = 0.89 + 0.83 * lambda [cm^-1] ; _exptl_special_details ; For peak integration a local UB matrix refined for each frame, using approximately 25 reflections. Hence _cell_measurement_reflns_used 25 For final cell dimensions an average of all local cells was performed and estimated standard uncertainties were obtained from the spread of the local observations Because of the nature of the experiment, it is not possible to give values of theta_min and theta_max for the cell determination. Instead, we can give values of _cell_measurement_sin(theta)/lambda_min 0.10 _cell_measurement_sin(theta)/lambda_max 0.70 The same applies for the wavelength used for the experiment. The range of wavelengths used was 0.5-5.0 Angstroms, BUT the bulk of the diffraction information is obtained from wavelengths in the range 0.7-2.5 Angstroms. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.5-5.0 _diffrn_radiation_type neutron _diffrn_radiation_source 'ISIS spallation source' _diffrn_radiation_monochromator none _diffrn_measurement_device SXD _diffrn_measurement_method 'time of flight LAUE diffraction' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4714 _diffrn_reflns_av_R_equivalents 0.062 _diffrn_reflns_av_sigmaI/netI 0.0894 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -48 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min ? _diffrn_reflns_theta_max ? _reflns_number_total 1473 _reflns_number_gt 1472 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; The variable wavelength nature of the data collection procedure means that sensible values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max cannot be given It is also difficult to estimate realistic values of maximum sin(theta)/lambda values for two reasons: (i) Different sin(theta)/lambda ranges are accessed in different parts of the detectors (ii) The nature of the data collection occasionally allows some reflections at very high sin(theta)/lambda to be observed even when no real attempt has been made to measure data in this region. However, we can attempt to estimate the sin(theta)/lambda limits as follows: _diffrn_reflns_sin(theta)/lambda_min 0.10 _diffrn_reflns_sin(theta)/lambda_max 0.95 Note also that reflections for which the standard profile fitting integration procedure fails are excluded from the data set, thus resulting in a high elimination rate of very weak or "unobserved" peaks from the final data set. The extinction coefficient reported in _refine_ls_extinction_coef is in this case the refined value of the mosaic spread in units of 10^-4 rad^-1 The reference for the extinction method used is: Becker, P. & Coppens, P. (1974). Acta Cryst. A30, 129-148. ; _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method 'Becker-Coppens Lorentzian model' _refine_ls_extinction_coef 0.165 _refine_ls_number_reflns 1473 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0777 _refine_ls_R_factor_gt 0.0776 _refine_ls_wR_factor_ref 0.1461 _refine_ls_wR_factor_gt 0.1460 _refine_ls_goodness_of_fit_ref 1.222 _refine_ls_restrained_S_all 1.222 _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 C1 C 0.1845(5) 0.9468(3) 0.52221(13) 0.0085(7) Uani 1 1 d . . . C2 C 0.0781(5) 0.8813(3) 0.55545(14) 0.0111(7) Uani 1 1 d . . . C3 C 0.0354(5) 0.9297(4) 0.60630(14) 0.0135(8) Uani 1 1 d . . . C4 C 0.0951(5) 1.0440(3) 0.62450(15) 0.0117(7) Uani 1 1 d . . . C5 C 0.1997(5) 1.1092(3) 0.59140(13) 0.0122(7) Uani 1 1 d . . . C6 C 0.2446(5) 1.0622(3) 0.54062(13) 0.0109(7) Uani 1 1 d . . . C7 C 0.4697(5) 0.9608(3) 0.33940(13) 0.0086(7) Uani 1 1 d . . . C8 C 0.5224(5) 0.8870(3) 0.29552(14) 0.0126(8) Uani 1 1 d . . . C9 C 0.6261(5) 0.9355(4) 0.25669(13) 0.0125(7) Uani 1 1 d . . . C10 C 0.6744(5) 1.0602(3) 0.26077(15) 0.0162(8) Uani 1 1 d . . . C11 C 0.6216(6) 1.1351(3) 0.30452(15) 0.0158(9) Uani 1 1 d . . . C12 C 0.5211(5) 1.0860(3) 0.34374(13) 0.0106(7) Uani 1 1 d . . . C13 C 0.2254(5) 0.8943(3) 0.46731(13) 0.0104(7) Uani 1 1 d . . . C14 C 0.3340(5) 0.9554(3) 0.43192(14) 0.0102(7) Uani 1 1 d . . . C15 C 0.3608(5) 0.9054(3) 0.37982(12) 0.0087(7) Uani 1 1 d . . . O16 O 0.1606(6) 0.7923(4) 0.45230(17) 0.0130(9) Uani 1 1 d . . . O17 O 0.2904(6) 0.8026(4) 0.36349(17) 0.0148(10) Uani 1 1 d . . . H18 H 0.0279(12) 0.7934(8) 0.5402(4) 0.033(2) Uani 1 1 d . . . H19 H -0.0454(11) 0.8792(8) 0.6318(3) 0.030(2) Uani 1 1 d . . . H20 H 0.0646(11) 1.0796(8) 0.6648(3) 0.031(2) Uani 1 1 d . . . H21 H 0.2469(11) 1.2004(8) 0.6047(3) 0.029(2) Uani 1 1 d . . . H22 H 0.3218(11) 1.1169(7) 0.5151(3) 0.0273(19) Uani 1 1 d . . . H23 H 0.4852(11) 0.7891(8) 0.2933(3) 0.0286(19) Uani 1 1 d . . . H24 H 0.6683(13) 0.8765(9) 0.2239(4) 0.038(2) Uani 1 1 d . . . H25 H 0.7565(13) 1.0993(9) 0.2311(3) 0.037(2) Uani 1 1 d . . . H26 H 0.6590(13) 1.2327(8) 0.3070(4) 0.036(2) Uani 1 1 d . . . H27 H 0.4844(12) 1.1465(8) 0.3770(3) 0.030(2) Uani 1 1 d . . . H28 H 0.3940(13) 1.0395(7) 0.4445(4) 0.033(2) Uani 1 1 d . . . H29 H 0.2215(13) 0.7775(7) 0.4006(4) 0.034(2) 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 0.006(2) 0.0103(14) 0.0095(13) 0.0028(11) -0.0006(11) 0.0020(15) C2 0.006(2) 0.0111(15) 0.0162(16) 0.0037(13) 0.0031(12) -0.0004(16) C3 0.011(2) 0.0144(16) 0.0147(15) 0.0042(13) 0.0035(13) -0.0025(17) C4 0.005(2) 0.0156(15) 0.0145(16) 0.0029(13) 0.0038(12) 0.0014(16) C5 0.011(2) 0.0122(14) 0.0132(15) -0.0019(12) 0.0039(12) -0.0028(16) C6 0.013(2) 0.0100(14) 0.0096(13) 0.0013(12) 0.0012(12) -0.0006(15) C7 0.007(2) 0.0090(13) 0.0102(14) -0.0008(11) 0.0001(11) 0.0031(15) C8 0.015(2) 0.0116(14) 0.0106(14) -0.0055(12) 0.0003(13) 0.0039(17) C9 0.007(2) 0.0185(16) 0.0120(15) -0.0034(14) 0.0019(12) 0.0018(15) C10 0.019(3) 0.0164(16) 0.0129(15) -0.0008(13) 0.0045(14) 0.0007(18) C11 0.019(3) 0.0128(16) 0.0156(16) 0.0001(12) 0.0053(14) 0.0034(16) C12 0.013(2) 0.0090(14) 0.0094(14) -0.0012(11) 0.0041(12) -0.0010(15) C13 0.012(2) 0.0088(14) 0.0103(14) 0.0017(11) -0.0018(12) 0.0005(15) C14 0.011(2) 0.0102(14) 0.0096(13) -0.0019(11) 0.0019(11) -0.0005(16) C15 0.007(2) 0.0099(14) 0.0090(13) -0.0018(11) -0.0001(11) 0.0032(14) O16 0.011(3) 0.0113(16) 0.0172(19) 0.0001(14) -0.0023(15) -0.0061(18) O17 0.018(3) 0.0108(17) 0.016(2) -0.0035(14) -0.0005(16) -0.002(2) H18 0.035(7) 0.015(3) 0.050(5) -0.007(3) 0.002(4) -0.007(4) H19 0.021(5) 0.035(4) 0.034(4) 0.006(4) 0.014(3) -0.008(4) H20 0.034(6) 0.031(4) 0.028(4) 0.001(3) 0.009(3) 0.001(4) H21 0.030(6) 0.027(4) 0.031(4) -0.010(3) 0.004(4) -0.008(4) H22 0.031(6) 0.031(4) 0.020(4) -0.004(3) 0.009(3) -0.010(4) H23 0.026(6) 0.027(4) 0.032(4) -0.006(3) 0.005(4) -0.002(4) H24 0.042(7) 0.036(4) 0.035(5) -0.019(4) 0.007(4) 0.005(5) H25 0.038(7) 0.042(5) 0.032(4) 0.001(4) 0.019(4) -0.005(5) H26 0.039(7) 0.027(4) 0.041(5) -0.005(4) 0.011(4) -0.009(4) H27 0.034(6) 0.022(4) 0.034(4) -0.009(3) 0.015(4) -0.001(4) H28 0.041(7) 0.021(4) 0.035(4) -0.008(3) 0.012(4) -0.017(4) H29 0.030(6) 0.019(4) 0.055(6) 0.004(3) -0.009(4) -0.006(4) _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 C6 1.406(5) . ? C1 C2 1.408(5) . ? C1 C13 1.489(5) . ? C2 C3 1.389(5) . ? C2 H18 1.095(9) . ? C3 C4 1.393(5) . ? C3 H19 1.077(9) . ? C4 C5 1.395(5) . ? C4 H20 1.084(10) . ? C5 C6 1.388(5) . ? C5 H21 1.100(9) . ? C6 H22 1.080(9) . ? C7 C12 1.409(5) . ? C7 C8 1.401(5) . ? C7 C15 1.481(5) . ? C8 C9 1.399(5) . ? C8 H23 1.092(10) . ? C9 C10 1.395(5) . ? C9 H24 1.078(9) . ? C10 C11 1.405(5) . ? C10 H25 1.093(10) . ? C11 C12 1.391(5) . ? C11 H26 1.090(9) . ? C12 H27 1.081(8) . ? C13 O16 1.275(5) . ? C13 C14 1.429(5) . ? C14 C15 1.394(5) . ? C14 H28 1.079(9) . ? C15 O17 1.313(5) . ? O16 H29 1.372(12) . ? O17 H29 1.113(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 C6 C1 C2 119.4(3) . . ? C6 C1 C13 121.7(3) . . ? C2 C1 C13 118.9(3) . . ? C3 C2 C1 120.0(3) . . ? C3 C2 H18 120.9(6) . . ? C1 C2 H18 119.1(6) . . ? C2 C3 C4 120.6(3) . . ? C2 C3 H19 120.0(6) . . ? C4 C3 H19 119.5(5) . . ? C5 C4 C3 119.4(3) . . ? C5 C4 H20 120.3(6) . . ? C3 C4 H20 120.2(6) . . ? C6 C5 C4 121.0(3) . . ? C6 C5 H21 118.4(5) . . ? C4 C5 H21 120.6(5) . . ? C5 C6 C1 119.7(3) . . ? C5 C6 H22 119.2(5) . . ? C1 C6 H22 121.0(5) . . ? C12 C7 C8 119.0(3) . . ? C12 C7 C15 121.7(3) . . ? C8 C7 C15 119.2(3) . . ? C9 C8 C7 121.0(3) . . ? C9 C8 H23 120.4(5) . . ? C7 C8 H23 118.5(6) . . ? C10 C9 C8 119.6(3) . . ? C10 C9 H24 120.4(7) . . ? C8 C9 H24 120.0(7) . . ? C9 C10 C11 119.8(3) . . ? C9 C10 H25 120.6(6) . . ? C11 C10 H25 119.6(6) . . ? C12 C11 C10 120.5(3) . . ? C12 C11 H26 120.4(6) . . ? C10 C11 H26 119.1(6) . . ? C11 C12 C7 120.0(3) . . ? C11 C12 H27 118.2(6) . . ? C7 C12 H27 121.8(6) . . ? O16 C13 C14 120.2(3) . . ? O16 C13 C1 118.2(4) . . ? C14 C13 C1 121.7(3) . . ? C15 C14 C13 118.9(3) . . ? C15 C14 H28 119.7(6) . . ? C13 C14 H28 121.4(6) . . ? O17 C15 C14 121.1(4) . . ? O17 C15 C7 115.1(3) . . ? C14 C15 C7 123.8(3) . . ? C13 O16 H29 101.1(5) . . ? C15 O17 H29 101.7(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 C6 C1 C2 C3 -1.1(6) . . . . ? C13 C1 C2 C3 -178.6(4) . . . . ? C1 C2 C3 C4 1.0(6) . . . . ? C2 C3 C4 C5 -0.6(6) . . . . ? C3 C4 C5 C6 0.2(6) . . . . ? C4 C5 C6 C1 -0.3(6) . . . . ? C2 C1 C6 C5 0.7(6) . . . . ? C13 C1 C6 C5 178.1(3) . . . . ? C12 C7 C8 C9 0.8(6) . . . . ? C15 C7 C8 C9 -179.5(4) . . . . ? C7 C8 C9 C10 -1.8(6) . . . . ? C8 C9 C10 C11 1.6(6) . . . . ? C9 C10 C11 C12 -0.2(6) . . . . ? C10 C11 C12 C7 -0.9(6) . . . . ? C8 C7 C12 C11 0.6(6) . . . . ? C15 C7 C12 C11 -179.1(4) . . . . ? C6 C1 C13 O16 -176.6(4) . . . . ? C2 C1 C13 O16 0.8(5) . . . . ? C6 C1 C13 C14 3.4(5) . . . . ? C2 C1 C13 C14 -179.2(4) . . . . ? O16 C13 C14 C15 3.6(6) . . . . ? C1 C13 C14 C15 -176.4(3) . . . . ? C13 C14 C15 O17 -1.3(6) . . . . ? C13 C14 C15 C7 179.5(4) . . . . ? C12 C7 C15 O17 162.3(4) . . . . ? C8 C7 C15 O17 -17.4(5) . . . . ? C12 C7 C15 C14 -18.5(6) . . . . ? C8 C7 C15 C14 161.8(4) . . . . ? _refine_diff_density_max 0.141 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.035 data_dbm123 _database_code_depnum_ccdc_archive 'CCDC 739587' _audit_creation_method SHELXL-97 _chemical_name_systematic ; dibenzoylmethane ; _chemical_name_common dibenzoylmethane _chemical_melting_point ? _chemical_formula_moiety 'C15 O2 H12' _chemical_formula_sum 'C15 H12 O2' _chemical_formula_weight 224.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 6.646 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H -3.739 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 5.803 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 8.6251(5) _cell_length_b 10.6442(8) _cell_length_c 24.3193(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2232.7(3) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 2.5 _exptl_crystal_size_mid 2.0 _exptl_crystal_size_min 1.5 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 53 _exptl_absorpt_coefficient_mu '1.72, at 1 Angstrom' _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.513 _exptl_absorpt_correction_T_max 0.773 _exptl_absorpt_process_details ; The linear absorption coefficient is wavelength dependent and it is calculated as: mu = 0.89 + 0.83 * lambda [cm^-1] ; _exptl_special_details ; For peak integration a local UB matrix refined for each frame, using approximately 25 reflections. Hence _cell_measurement_reflns_used 25 For final cell dimensions an average of all local cells was performed and estimated standard uncertainties were obtained from the spread of the local observations Because of the nature of the experiment, it is not possible to give values of theta_min and theta_max for the cell determination. Instead, we can give values of _cell_measurement_sin(theta)/lambda_min 0.10 _cell_measurement_sin(theta)/lambda_max 0.70 The same applies for the wavelength used for the experiment. The range of wavelengths used was 0.5-5.0 Angstroms, BUT the bulk of the diffraction information is obtained from wavelengths in the range 0.7-2.5 Angstroms. ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.5-5.0 _diffrn_radiation_type neutron _diffrn_radiation_source 'ISIS spallation source' _diffrn_radiation_monochromator none _diffrn_measurement_device SXD _diffrn_measurement_method 'time of flight LAUE diffraction' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6947 _diffrn_reflns_av_R_equivalents 0.063 _diffrn_reflns_av_sigmaI/netI 0.0629 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -74 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min ? _diffrn_reflns_theta_max ? _reflns_number_total 2481 _reflns_number_gt 2481 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; The variable wavelength nature of the data collection procedure means that sensible values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max cannot be given It is also difficult to estimate realistic values of maximum sin(theta)/lambda values for two reasons: (i) Different sin(theta)/lambda ranges are accessed in different parts of the detectors (ii) The nature of the data collection occasionally allows some reflections at very high sin(theta)/lambda to be observed even when no real attempt has been made to measure data in this region. However, we can attempt to estimate the sin(theta)/lambda limits as follows: _diffrn_reflns_sin(theta)/lambda_min 0.10 _diffrn_reflns_sin(theta)/lambda_max 1.00 Note also that reflections for which the standard profile fitting integration procedure fails are excluded from the data set, thus resulting in a high elimination rate of very weak or "unobserved" peaks from the final data set. The extinction coefficient reported in _refine_ls_extinction_coef is in this case the refined value of the mosaic spread in units of 10^-4 rad^-1 The reference for the extinction method used is: Becker, P. & Coppens, P. (1974). Acta Cryst. A30, 129-148. ; _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method 'Becker-Coppens Lorentzian model' _refine_ls_extinction_coef 0.165 _refine_ls_number_reflns 2481 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0721 _refine_ls_R_factor_gt 0.0721 _refine_ls_wR_factor_ref 0.1417 _refine_ls_wR_factor_gt 0.1417 _refine_ls_goodness_of_fit_ref 1.222 _refine_ls_restrained_S_all 1.222 _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 C1 C 0.1847(2) 0.94629(15) 0.52177(6) 0.0101(3) Uani 1 1 d . . . C2 C 0.0787(2) 0.88108(16) 0.55487(7) 0.0139(3) Uani 1 1 d . . . C3 C 0.0358(3) 0.92904(18) 0.60598(7) 0.0161(4) Uani 1 1 d . . . C4 C 0.0969(2) 1.04273(18) 0.62438(7) 0.0157(3) Uani 1 1 d . . . C5 C 0.2000(2) 1.10909(18) 0.59114(7) 0.0155(4) Uani 1 1 d . . . C6 C 0.2445(2) 1.06120(16) 0.54031(6) 0.0125(3) Uani 1 1 d . . . C7 C 0.4700(2) 0.96194(16) 0.33920(6) 0.0106(3) Uani 1 1 d . . . C8 C 0.5229(2) 0.88724(17) 0.29556(7) 0.0147(3) Uani 1 1 d . . . C9 C 0.6250(3) 0.93668(19) 0.25691(7) 0.0174(4) Uani 1 1 d . . . C10 C 0.6736(3) 1.06150(19) 0.26090(7) 0.0194(4) Uani 1 1 d . . . C11 C 0.6214(3) 1.13568(18) 0.30433(8) 0.0174(4) Uani 1 1 d . . . C12 C 0.5208(2) 1.08632(17) 0.34365(7) 0.0137(3) Uani 1 1 d . . . C13 C 0.2257(2) 0.89415(15) 0.46724(7) 0.0111(3) Uani 1 1 d . . . C14 C 0.3339(2) 0.95527(16) 0.43162(7) 0.0119(3) Uani 1 1 d . . . C15 C 0.3613(2) 0.90566(15) 0.37963(6) 0.0107(3) Uani 1 1 d . . . O16 O 0.1605(3) 0.7926(2) 0.45229(8) 0.0170(4) Uani 1 1 d . . . O17 O 0.2909(3) 0.80327(19) 0.36302(8) 0.0168(4) Uani 1 1 d . . . H18 H 0.0292(7) 0.7949(4) 0.5399(2) 0.0361(11) Uani 1 1 d . . . H19 H -0.0459(7) 0.8771(4) 0.63167(19) 0.0363(11) Uani 1 1 d . . . H20 H 0.0627(7) 1.0788(5) 0.66407(17) 0.0374(12) Uani 1 1 d . . . H21 H 0.2472(7) 1.1982(4) 0.60498(17) 0.0370(11) Uani 1 1 d . . . H22 H 0.3237(6) 1.1153(4) 0.51501(17) 0.0323(11) Uani 1 1 d . . . H23 H 0.4834(6) 0.7915(4) 0.29226(19) 0.0339(10) Uani 1 1 d . . . H24 H 0.6676(7) 0.8774(5) 0.22371(19) 0.0378(12) Uani 1 1 d . . . H25 H 0.7528(7) 1.0996(5) 0.23072(19) 0.0398(12) Uani 1 1 d . . . H26 H 0.6598(7) 1.2321(4) 0.3076(2) 0.0380(12) Uani 1 1 d . . . H27 H 0.4824(6) 1.1451(4) 0.37750(19) 0.0324(10) Uani 1 1 d . . . H28 H 0.3915(6) 1.0385(4) 0.44431(17) 0.0297(10) Uani 1 1 d . . . H29 H 0.2201(7) 0.7771(4) 0.4004(2) 0.0396(12) 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 0.0087(9) 0.0103(6) 0.0113(6) 0.0029(5) -0.0002(5) -0.0007(6) C2 0.0123(10) 0.0111(6) 0.0182(8) 0.0031(6) 0.0028(6) -0.0005(6) C3 0.0149(11) 0.0157(7) 0.0175(8) 0.0054(6) 0.0060(6) -0.0003(8) C4 0.0132(10) 0.0195(8) 0.0143(7) 0.0024(6) 0.0048(6) -0.0013(7) C5 0.0168(11) 0.0161(7) 0.0134(8) -0.0004(6) 0.0039(6) -0.0029(7) C6 0.0126(10) 0.0134(6) 0.0115(6) 0.0010(5) 0.0021(5) -0.0033(7) C7 0.0096(9) 0.0116(6) 0.0106(6) -0.0009(5) -0.0002(5) 0.0024(6) C8 0.0149(10) 0.0157(7) 0.0135(7) -0.0048(6) -0.0015(6) 0.0024(7) C9 0.0177(11) 0.0221(8) 0.0124(7) -0.0047(6) 0.0020(6) 0.0019(8) C10 0.0208(12) 0.0238(9) 0.0136(7) -0.0003(6) 0.0051(6) 0.0019(8) C11 0.0189(12) 0.0164(8) 0.0169(8) 0.0011(6) 0.0064(6) 0.0000(7) C12 0.0166(11) 0.0114(7) 0.0131(7) -0.0007(5) 0.0032(6) 0.0015(7) C13 0.0111(10) 0.0092(6) 0.0129(7) 0.0018(5) -0.0010(5) 0.0010(6) C14 0.0116(10) 0.0114(6) 0.0127(7) -0.0006(5) 0.0017(5) -0.0016(7) C15 0.0102(10) 0.0110(6) 0.0110(6) -0.0005(5) -0.0012(5) 0.0019(6) O16 0.0211(14) 0.0127(8) 0.0172(9) 0.0015(6) -0.0023(7) -0.0056(8) O17 0.0216(13) 0.0118(8) 0.0170(9) -0.0024(6) -0.0016(7) -0.0031(9) H18 0.044(3) 0.0220(17) 0.042(2) -0.0012(16) 0.0082(19) -0.012(2) H19 0.043(3) 0.033(2) 0.032(2) 0.0072(16) 0.0185(19) -0.009(2) H20 0.049(4) 0.039(2) 0.0246(19) -0.0066(17) 0.0151(18) -0.004(2) H21 0.047(3) 0.032(2) 0.032(2) -0.0096(16) 0.0112(19) -0.017(2) H22 0.041(3) 0.031(2) 0.0250(19) -0.0002(15) 0.0098(17) -0.020(2) H23 0.043(3) 0.0234(17) 0.035(2) -0.0107(15) 0.0033(18) -0.0037(19) H24 0.043(3) 0.042(3) 0.028(2) -0.0148(18) 0.0122(18) 0.004(2) H25 0.042(3) 0.047(3) 0.030(2) 0.0020(19) 0.016(2) -0.005(3) H26 0.049(4) 0.026(2) 0.039(2) -0.0019(17) 0.014(2) -0.009(2) H27 0.037(3) 0.0227(17) 0.037(2) -0.0108(16) 0.0160(18) 0.0020(19) H28 0.035(3) 0.0239(17) 0.0305(19) -0.0078(15) 0.0100(16) -0.0127(18) H29 0.040(3) 0.0206(18) 0.059(3) 0.0008(18) -0.013(2) -0.008(2) _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 C6 1.402(2) . ? C1 C2 1.402(2) . ? C1 C13 1.480(2) . ? C2 C3 1.394(3) . ? C2 H18 1.076(5) . ? C3 C4 1.393(3) . ? C3 H19 1.092(5) . ? C4 C5 1.394(3) . ? C4 H20 1.080(4) . ? C5 C6 1.391(2) . ? C5 H21 1.086(5) . ? C6 H22 1.084(5) . ? C7 C12 1.399(2) . ? C7 C8 1.402(2) . ? C7 C15 1.485(3) . ? C8 C9 1.392(3) . ? C8 H23 1.077(5) . ? C9 C10 1.396(3) . ? C9 H24 1.089(5) . ? C10 C11 1.393(3) . ? C10 H25 1.082(5) . ? C11 C12 1.394(3) . ? C11 H26 1.081(5) . ? C12 H27 1.086(4) . ? C13 O16 1.271(3) . ? C13 C14 1.430(3) . ? C14 C15 1.390(2) . ? C14 H28 1.061(5) . ? C15 O17 1.311(3) . ? O16 H29 1.372(6) . ? O17 H29 1.130(7) . ? 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 C6 C1 C2 119.15(15) . . ? C6 C1 C13 121.82(15) . . ? C2 C1 C13 118.99(15) . . ? C3 C2 C1 120.26(17) . . ? C3 C2 H18 120.6(3) . . ? C1 C2 H18 119.1(3) . . ? C2 C3 C4 120.26(17) . . ? C2 C3 H19 119.8(3) . . ? C4 C3 H19 120.0(3) . . ? C5 C4 C3 119.67(16) . . ? C5 C4 H20 120.8(3) . . ? C3 C4 H20 119.5(3) . . ? C6 C5 C4 120.37(17) . . ? C6 C5 H21 119.5(3) . . ? C4 C5 H21 120.2(3) . . ? C5 C6 C1 120.27(16) . . ? C5 C6 H22 118.9(3) . . ? C1 C6 H22 120.8(3) . . ? C12 C7 C8 119.55(16) . . ? C12 C7 C15 121.91(15) . . ? C8 C7 C15 118.54(15) . . ? C9 C8 C7 120.17(17) . . ? C9 C8 H23 120.5(3) . . ? C7 C8 H23 119.3(3) . . ? C10 C9 C8 120.18(17) . . ? C10 C9 H24 120.1(3) . . ? C8 C9 H24 119.7(3) . . ? C9 C10 C11 119.68(17) . . ? C9 C10 H25 119.9(3) . . ? C11 C10 H25 120.4(3) . . ? C12 C11 C10 120.49(17) . . ? C12 C11 H26 119.8(3) . . ? C10 C11 H26 119.7(3) . . ? C11 C12 C7 119.91(16) . . ? C11 C12 H27 119.5(3) . . ? C7 C12 H27 120.6(3) . . ? O16 C13 C14 120.16(17) . . ? O16 C13 C1 117.96(18) . . ? C14 C13 C1 121.88(15) . . ? C15 C14 C13 119.29(16) . . ? C15 C14 H28 120.1(3) . . ? C13 C14 H28 120.6(3) . . ? O17 C15 C14 121.13(18) . . ? O17 C15 C7 115.07(16) . . ? C14 C15 C7 123.80(15) . . ? C13 O16 H29 101.5(3) . . ? C15 O17 H29 101.9(3) . . ? 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 C6 C1 C2 C3 -1.1(3) . . . . ? C13 C1 C2 C3 -178.85(18) . . . . ? C1 C2 C3 C4 0.5(3) . . . . ? C2 C3 C4 C5 0.7(3) . . . . ? C3 C4 C5 C6 -1.3(3) . . . . ? C4 C5 C6 C1 0.7(3) . . . . ? C2 C1 C6 C5 0.5(3) . . . . ? C13 C1 C6 C5 178.18(18) . . . . ? C12 C7 C8 C9 -0.1(3) . . . . ? C15 C7 C8 C9 -179.89(18) . . . . ? C7 C8 C9 C10 -1.0(3) . . . . ? C8 C9 C10 C11 1.2(3) . . . . ? C9 C10 C11 C12 -0.2(3) . . . . ? C10 C11 C12 C7 -0.9(3) . . . . ? C8 C7 C12 C11 1.0(3) . . . . ? C15 C7 C12 C11 -179.19(19) . . . . ? C6 C1 C13 O16 -176.5(2) . . . . ? C2 C1 C13 O16 1.2(3) . . . . ? C6 C1 C13 C14 2.9(3) . . . . ? C2 C1 C13 C14 -179.48(18) . . . . ? O16 C13 C14 C15 2.9(3) . . . . ? C1 C13 C14 C15 -176.41(17) . . . . ? C13 C14 C15 O17 -0.7(3) . . . . ? C13 C14 C15 C7 179.49(17) . . . . ? C12 C7 C15 O17 162.1(2) . . . . ? C8 C7 C15 O17 -18.1(3) . . . . ? C12 C7 C15 C14 -18.1(3) . . . . ? C8 C7 C15 C14 161.69(18) . . . . ? _refine_diff_density_max 0.157 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.035 data_dbm160 _database_code_depnum_ccdc_archive 'CCDC 739588' _audit_creation_method SHELXL-97 _chemical_name_systematic ; dibenzoylmethane ; _chemical_name_common dibenzoylmethane _chemical_melting_point ? _chemical_formula_moiety 'C15 O2 H12' _chemical_formula_sum 'C15 H12 O2' _chemical_formula_weight 224.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 6.646 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H -3.739 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 5.803 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 8.6594(7) _cell_length_b 10.7139(11) _cell_length_c 24.359(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2260.0(4) _cell_formula_units_Z 8 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 2.5 _exptl_crystal_size_mid 2.0 _exptl_crystal_size_min 1.5 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 53 _exptl_absorpt_coefficient_mu '1.72, at 1 Angstrom' _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.513 _exptl_absorpt_correction_T_max 0.773 _exptl_absorpt_process_details ; The linear absorption coefficient is wavelength dependent and it is calculated as: mu = 0.89 + 0.83 * lambda [cm^-1] ; _exptl_special_details ; For peak integration a local UB matrix refined for each frame, using approximately 25 reflections. Hence _cell_measurement_reflns_used 25 For final cell dimensions an average of all local cells was performed and estimated standard uncertainties were obtained from the spread of the local observations Because of the nature of the experiment, it is not possible to give values of theta_min and theta_max for the cell determination. Instead, we can give values of _cell_measurement_sin(theta)/lambda_min 0.10 _cell_measurement_sin(theta)/lambda_max 0.70 The same applies for the wavelength used for the experiment. The range of wavelengths used was 0.5-5.0 Angstroms, BUT the bulk of the diffraction information is obtained from wavelengths in the range 0.7-2.5 Angstroms. ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 0.5-5.0 _diffrn_radiation_type neutron _diffrn_radiation_source 'ISIS spallation source' _diffrn_radiation_monochromator none _diffrn_measurement_device SXD _diffrn_measurement_method 'time of flight LAUE diffraction' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3614 _diffrn_reflns_av_R_equivalents 0.068 _diffrn_reflns_av_sigmaI/netI 0.0761 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -72 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min ? _diffrn_reflns_theta_max ? _reflns_number_total 1204 _reflns_number_gt 1203 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; The variable wavelength nature of the data collection procedure means that sensible values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max cannot be given It is also difficult to estimate realistic values of maximum sin(theta)/lambda values for two reasons: (i) Different sin(theta)/lambda ranges are accessed in different parts of the detectors (ii) The nature of the data collection occasionally allows some reflections at very high sin(theta)/lambda to be observed even when no real attempt has been made to measure data in this region. However, we can attempt to estimate the sin(theta)/lambda limits as follows: _diffrn_reflns_sin(theta)/lambda_min 0.10 _diffrn_reflns_sin(theta)/lambda_max 0.88 Note also that reflections for which the standard profile fitting integration procedure fails are excluded from the data set, thus resulting in a high elimination rate of very weak or "unobserved" peaks from the final data set. The extinction coefficient reported in _refine_ls_extinction_coef is in this case the refined value of the mosaic spread in units of 10^-4 rad^-1 The reference for the extinction method used is: Becker, P. & Coppens, P. (1974). Acta Cryst. A30, 129-148. ; _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method 'Becker-Coppens Lorentzian model' _refine_ls_extinction_coef 0.165 _refine_ls_number_reflns 1204 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0708 _refine_ls_R_factor_gt 0.0708 _refine_ls_wR_factor_ref 0.1368 _refine_ls_wR_factor_gt 0.1368 _refine_ls_goodness_of_fit_ref 1.192 _refine_ls_restrained_S_all 1.192 _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 C1 C 0.1852(5) 0.9461(3) 0.52107(14) 0.0162(8) Uani 1 1 d . . . C2 C 0.0797(6) 0.8799(4) 0.55433(17) 0.0223(10) Uani 1 1 d . . . C3 C 0.0375(6) 0.9285(4) 0.60552(16) 0.0249(11) Uani 1 1 d . . . C4 C 0.0967(6) 1.0426(4) 0.62364(17) 0.0221(10) Uani 1 1 d . . . C5 C 0.2009(6) 1.1079(4) 0.59085(15) 0.0229(10) Uani 1 1 d . . . C6 C 0.2445(5) 1.0599(4) 0.54000(15) 0.0193(9) Uani 1 1 d . . . C7 C 0.4692(5) 0.9626(3) 0.33915(14) 0.0167(8) Uani 1 1 d . . . C8 C 0.5231(6) 0.8889(4) 0.29529(16) 0.0224(9) Uani 1 1 d . . . C9 C 0.6260(6) 0.9393(4) 0.25663(16) 0.0266(10) Uani 1 1 d . . . C10 C 0.6722(6) 1.0625(4) 0.26106(17) 0.0282(11) Uani 1 1 d . . . C11 C 0.6206(6) 1.1368(4) 0.30441(16) 0.0266(11) Uani 1 1 d . . . C12 C 0.5200(5) 1.0866(4) 0.34363(15) 0.0205(9) Uani 1 1 d . . . C13 C 0.2262(5) 0.8942(3) 0.46663(15) 0.0178(9) Uani 1 1 d . . . C14 C 0.3341(5) 0.9551(3) 0.43130(14) 0.0172(9) Uani 1 1 d . . . C15 C 0.3616(5) 0.9056(3) 0.37906(14) 0.0173(9) Uani 1 1 d . . . O16 O 0.1616(6) 0.7925(4) 0.4523(2) 0.0239(12) Uani 1 1 d . . . O17 O 0.2918(7) 0.8043(4) 0.36251(19) 0.0261(12) Uani 1 1 d . . . H18 H 0.0327(13) 0.7934(9) 0.5395(4) 0.045(3) Uani 1 1 d . . . H19 H -0.0438(15) 0.8776(10) 0.6311(4) 0.050(3) Uani 1 1 d . . . H20 H 0.0633(14) 1.0776(10) 0.6637(4) 0.049(3) Uani 1 1 d . . . H21 H 0.2461(13) 1.1972(9) 0.6040(4) 0.047(3) Uani 1 1 d . . . H22 H 0.3235(12) 1.1134(8) 0.5145(3) 0.040(2) Uani 1 1 d . . . H23 H 0.4871(14) 0.7926(8) 0.2923(4) 0.045(3) Uani 1 1 d . . . H24 H 0.6685(14) 0.8792(10) 0.2234(4) 0.050(3) Uani 1 1 d . . . H25 H 0.7536(13) 1.1032(11) 0.2307(4) 0.049(3) Uani 1 1 d . . . H26 H 0.6565(14) 1.2326(8) 0.3076(4) 0.046(3) Uani 1 1 d . . . H27 H 0.4814(14) 1.1452(9) 0.3772(4) 0.044(3) Uani 1 1 d . . . H28 H 0.3905(14) 1.0384(8) 0.4437(4) 0.044(3) Uani 1 1 d . . . H29 H 0.2208(14) 0.7769(9) 0.4004(4) 0.047(3) 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 0.013(2) 0.0179(17) 0.0177(16) 0.0047(13) 0.0003(13) 0.0040(18) C2 0.018(3) 0.0198(19) 0.029(2) 0.0052(17) 0.0045(16) 0.0018(19) C3 0.022(3) 0.028(2) 0.0255(19) 0.0077(17) 0.0075(17) -0.004(2) C4 0.014(3) 0.027(2) 0.025(2) -0.0005(17) 0.0082(16) 0.0022(19) C5 0.026(3) 0.0231(19) 0.0192(18) -0.0006(15) 0.0050(16) -0.005(2) C6 0.017(3) 0.0218(18) 0.0192(17) 0.0047(15) 0.0001(15) -0.0039(17) C7 0.015(2) 0.0172(17) 0.0181(18) -0.0009(13) -0.0025(14) 0.0072(18) C8 0.024(3) 0.024(2) 0.0194(18) -0.0089(15) 0.0014(16) 0.004(2) C9 0.026(3) 0.034(2) 0.0198(19) -0.0058(17) 0.0020(17) 0.003(2) C10 0.026(3) 0.034(2) 0.024(2) 0.0004(17) 0.0077(17) 0.001(2) C11 0.030(3) 0.024(2) 0.026(2) 0.0013(16) 0.0087(18) 0.001(2) C12 0.024(3) 0.0167(17) 0.0207(18) -0.0021(15) 0.0032(16) 0.0031(19) C13 0.017(3) 0.0156(17) 0.0209(17) 0.0054(14) -0.0004(14) 0.0006(18) C14 0.014(2) 0.0201(19) 0.0178(16) -0.0034(14) 0.0034(13) 0.0020(19) C15 0.018(3) 0.0160(16) 0.0177(15) -0.0016(14) -0.0034(14) 0.0017(17) O16 0.024(4) 0.018(2) 0.030(2) 0.0025(18) -0.007(2) -0.008(2) O17 0.034(4) 0.019(2) 0.026(2) -0.0023(18) -0.002(2) -0.005(2) H18 0.044(7) 0.032(5) 0.058(6) 0.002(4) 0.010(5) -0.011(5) H19 0.052(8) 0.053(6) 0.045(5) 0.012(4) 0.023(5) -0.014(6) H20 0.058(8) 0.051(6) 0.038(5) 0.000(4) 0.020(5) -0.006(6) H21 0.058(9) 0.047(6) 0.037(4) -0.015(4) 0.010(5) -0.023(5) H22 0.040(7) 0.045(5) 0.034(4) -0.006(4) 0.018(4) -0.021(5) H23 0.068(9) 0.027(4) 0.041(5) -0.010(4) 0.000(5) 0.003(5) H24 0.042(8) 0.059(6) 0.050(6) -0.020(5) 0.008(5) 0.003(6) H25 0.037(7) 0.068(7) 0.043(5) 0.001(5) 0.020(5) -0.003(6) H26 0.050(8) 0.031(5) 0.056(6) -0.004(4) 0.009(5) -0.003(5) H27 0.051(8) 0.033(4) 0.047(5) -0.011(4) 0.017(5) 0.004(5) H28 0.054(8) 0.030(4) 0.049(5) -0.007(4) 0.024(5) -0.027(5) H29 0.036(8) 0.039(5) 0.065(7) 0.005(4) -0.001(5) -0.016(5) _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 C6 1.401(6) . ? C1 C2 1.412(6) . ? C1 C13 1.481(5) . ? C2 C3 1.400(6) . ? C2 H18 1.075(12) . ? C3 C4 1.397(6) . ? C3 H19 1.086(11) . ? C4 C5 1.393(6) . ? C4 H20 1.085(11) . ? C5 C6 1.393(5) . ? C5 H21 1.082(11) . ? C6 H22 1.086(10) . ? C7 C12 1.404(6) . ? C7 C8 1.408(5) . ? C7 C15 1.479(6) . ? C8 C9 1.405(7) . ? C8 H23 1.081(11) . ? C9 C10 1.384(6) . ? C9 H24 1.097(11) . ? C10 C11 1.395(6) . ? C10 H25 1.110(11) . ? C11 C12 1.400(6) . ? C11 H26 1.076(10) . ? C12 H27 1.085(10) . ? C13 O16 1.273(6) . ? C13 C14 1.428(6) . ? C14 C15 1.399(5) . ? C14 H28 1.061(11) . ? C15 O17 1.306(6) . ? O16 H29 1.374(12) . ? O17 H29 1.147(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 C6 C1 C2 119.0(3) . . ? C6 C1 C13 122.3(3) . . ? C2 C1 C13 118.7(4) . . ? C3 C2 C1 119.6(4) . . ? C3 C2 H18 121.3(7) . . ? C1 C2 H18 119.1(6) . . ? C2 C3 C4 120.7(4) . . ? C2 C3 H19 119.6(7) . . ? C4 C3 H19 119.7(7) . . ? C5 C4 C3 119.7(4) . . ? C5 C4 H20 121.0(7) . . ? C3 C4 H20 119.2(7) . . ? C6 C5 C4 120.0(4) . . ? C6 C5 H21 119.4(6) . . ? C4 C5 H21 120.5(6) . . ? C5 C6 C1 121.0(4) . . ? C5 C6 H22 118.9(6) . . ? C1 C6 H22 120.1(5) . . ? C12 C7 C8 119.1(4) . . ? C12 C7 C15 122.5(3) . . ? C8 C7 C15 118.4(4) . . ? C9 C8 C7 120.3(4) . . ? C9 C8 H23 120.3(6) . . ? C7 C8 H23 119.5(7) . . ? C8 C9 C10 119.8(4) . . ? C8 C9 H24 118.8(7) . . ? C10 C9 H24 121.4(7) . . ? C9 C10 C11 120.7(4) . . ? C9 C10 H25 120.4(7) . . ? C11 C10 H25 118.9(7) . . ? C12 C11 C10 119.8(4) . . ? C12 C11 H26 119.8(6) . . ? C10 C11 H26 120.5(7) . . ? C11 C12 C7 120.3(3) . . ? C11 C12 H27 119.0(7) . . ? C7 C12 H27 120.7(7) . . ? O16 C13 C14 120.8(4) . . ? O16 C13 C1 117.5(4) . . ? C14 C13 C1 121.6(3) . . ? C15 C14 C13 119.1(4) . . ? C15 C14 H28 119.9(6) . . ? C13 C14 H28 121.0(6) . . ? O17 C15 C14 121.1(4) . . ? O17 C15 C7 115.6(4) . . ? C14 C15 C7 123.3(3) . . ? C13 O16 H29 101.1(5) . . ? C15 O17 H29 102.3(6) . . ? _refine_diff_density_max 0.124 _refine_diff_density_min -0.091 _refine_diff_density_rms 0.024 data_dbm200 _database_code_depnum_ccdc_archive 'CCDC 739589' _audit_creation_method SHELXL-97 _chemical_name_systematic ; dibenzoylmethane ; _chemical_name_common dibenzoylmethane _chemical_melting_point ? _chemical_formula_moiety 'C15 O2 H12' _chemical_formula_sum 'C15 H12 O2' _chemical_formula_weight 224.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 6.646 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H -3.739 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 5.803 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 8.6886(5) _cell_length_b 10.7434(7) _cell_length_c 24.4019(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2277.8(2) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 2.5 _exptl_crystal_size_mid 2.0 _exptl_crystal_size_min 1.5 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 53 _exptl_absorpt_coefficient_mu '1.72, at 1 Angstrom' _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.513 _exptl_absorpt_correction_T_max 0.773 _exptl_absorpt_process_details ; The linear absorption coefficient is wavelength dependent and it is calculated as: mu = 0.89 + 0.83 * lambda [cm^-1] ; _exptl_special_details ; For peak integration a local UB matrix refined for each frame, using approximately 25 reflections. Hence _cell_measurement_reflns_used 25 For final cell dimensions an average of all local cells was performed and estimated standard uncertainties were obtained from the spread of the local observations Because of the nature of the experiment, it is not possible to give values of theta_min and theta_max for the cell determination. Instead, we can give values of _cell_measurement_sin(theta)/lambda_min 0.10 _cell_measurement_sin(theta)/lambda_max 0.70 The same applies for the wavelength used for the experiment. The range of wavelengths used was 0.5-5.0 Angstroms, BUT the bulk of the diffraction information is obtained from wavelengths in the range 0.7-2.5 Angstroms. ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.5-5.0 _diffrn_radiation_type neutron _diffrn_radiation_source 'ISIS spallation source' _diffrn_radiation_monochromator none _diffrn_measurement_device SXD _diffrn_measurement_method 'time of flight LAUE diffraction' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2423 _diffrn_reflns_av_R_equivalents 0.068 _diffrn_reflns_av_sigmaI/netI 0.0702 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 1.21 _diffrn_reflns_theta_max 12.68 _reflns_number_total 969 _reflns_number_gt 969 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; The variable wavelength nature of the data collection procedure means that sensible values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max cannot be given It is also difficult to estimate realistic values of maximum sin(theta)/lambda values for two reasons: (i) Different sin(theta)/lambda ranges are accessed in different parts of the detectors (ii) The nature of the data collection occasionally allows some reflections at very high sin(theta)/lambda to be observed even when no real attempt has been made to measure data in this region. However, we can attempt to estimate the sin(theta)/lambda limits as follows: _diffrn_reflns_sin(theta)/lambda_min 0.10 _diffrn_reflns_sin(theta)/lambda_max 0.85 Note also that reflections for which the standard profile fitting integration procedure fails are excluded from the data set, thus resulting in a high elimination rate of very weak or "unobserved" peaks from the final data set. The extinction coefficient reported in _refine_ls_extinction_coef is in this case the refined value of the mosaic spread in units of 10^-4 rad^-1 The reference for the extinction method used is: Becker, P. & Coppens, P. (1974). Acta Cryst. A30, 129-148. ; _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method 'Becker-Coppens Lorentzian model' _refine_ls_extinction_coef 0.165 _refine_ls_number_reflns 969 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0714 _refine_ls_R_factor_gt 0.0714 _refine_ls_wR_factor_ref 0.1463 _refine_ls_wR_factor_gt 0.1463 _refine_ls_goodness_of_fit_ref 1.347 _refine_ls_restrained_S_all 1.347 _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 C1 C 0.1874(6) 0.9447(5) 0.52049(18) 0.0225(12) Uani 1 1 d . . . C2 C 0.0815(8) 0.8803(5) 0.5534(2) 0.0297(14) Uani 1 1 d . . . C3 C 0.0381(8) 0.9285(6) 0.6045(2) 0.0364(15) Uani 1 1 d . . . C4 C 0.0979(7) 1.0413(5) 0.6231(2) 0.0312(14) Uani 1 1 d . . . C5 C 0.1999(7) 1.1064(6) 0.5899(2) 0.0307(14) Uani 1 1 d . . . C6 C 0.2444(7) 1.0589(5) 0.53932(19) 0.0269(12) Uani 1 1 d . . . C7 C 0.4704(7) 0.9640(5) 0.33907(19) 0.0258(12) Uani 1 1 d . . . C8 C 0.5240(7) 0.8906(5) 0.2949(2) 0.0298(13) Uani 1 1 d . . . C9 C 0.6242(8) 0.9407(5) 0.2568(2) 0.0351(14) Uani 1 1 d . . . C10 C 0.6702(8) 1.0637(5) 0.2614(2) 0.0374(15) Uani 1 1 d . . . C11 C 0.6174(8) 1.1376(5) 0.3045(2) 0.0364(16) Uani 1 1 d . . . C12 C 0.5189(7) 1.0874(5) 0.3435(2) 0.0272(13) Uani 1 1 d . . . C13 C 0.2269(7) 0.8935(5) 0.4659(2) 0.0250(13) Uani 1 1 d . . . C14 C 0.3357(7) 0.9553(5) 0.43067(19) 0.0249(13) Uani 1 1 d . . . C15 C 0.3619(7) 0.9065(5) 0.37903(19) 0.0247(13) Uani 1 1 d . . . O16 O 0.1635(8) 0.7930(5) 0.4517(3) 0.0315(17) Uani 1 1 d . . . O17 O 0.2913(9) 0.8040(6) 0.3627(3) 0.0332(17) Uani 1 1 d . . . H18 H 0.0349(18) 0.7928(11) 0.5381(6) 0.056(3) Uani 1 1 d . . . H19 H -0.0393(16) 0.8756(12) 0.6310(5) 0.056(4) Uani 1 1 d . . . H20 H 0.0659(16) 1.0749(12) 0.6630(5) 0.053(3) Uani 1 1 d . . . H21 H 0.2474(16) 1.1948(13) 0.6032(5) 0.056(4) Uani 1 1 d . . . H22 H 0.3236(17) 1.1132(11) 0.5142(4) 0.050(4) Uani 1 1 d . . . H23 H 0.4862(16) 0.7935(10) 0.2923(5) 0.052(3) Uani 1 1 d . . . H24 H 0.6708(18) 0.8841(13) 0.2238(5) 0.061(4) Uani 1 1 d . . . H25 H 0.7537(19) 1.1039(14) 0.2313(5) 0.065(4) Uani 1 1 d . . . H26 H 0.656(2) 1.2331(12) 0.3083(5) 0.064(4) Uani 1 1 d . . . H27 H 0.4804(18) 1.1441(11) 0.3774(5) 0.055(4) Uani 1 1 d . . . H28 H 0.3910(19) 1.0387(11) 0.4433(5) 0.055(4) Uani 1 1 d . . . H29 H 0.2245(18) 0.7773(11) 0.3994(7) 0.061(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 0.015(3) 0.027(3) 0.025(2) 0.007(2) 0.002(2) 0.003(3) C2 0.026(4) 0.026(3) 0.037(3) 0.004(2) 0.005(2) -0.008(3) C3 0.032(4) 0.046(4) 0.032(3) 0.012(3) 0.007(3) -0.004(3) C4 0.023(4) 0.035(3) 0.035(3) 0.001(3) 0.006(3) 0.004(3) C5 0.025(4) 0.037(3) 0.030(3) -0.001(2) 0.009(2) -0.008(3) C6 0.023(4) 0.031(3) 0.027(2) 0.004(2) -0.003(2) -0.003(3) C7 0.021(4) 0.029(3) 0.027(3) 0.000(2) -0.007(2) 0.006(3) C8 0.035(4) 0.029(3) 0.025(2) -0.007(2) 0.000(3) 0.007(3) C9 0.037(4) 0.040(3) 0.028(3) -0.012(3) 0.006(3) 0.004(3) C10 0.036(5) 0.043(3) 0.034(3) 0.003(3) 0.012(3) 0.003(3) C11 0.040(5) 0.031(3) 0.038(3) 0.003(2) 0.007(3) 0.001(3) C12 0.030(4) 0.023(3) 0.029(3) -0.004(2) 0.002(2) 0.001(3) C13 0.020(4) 0.026(3) 0.029(2) 0.005(2) -0.002(2) 0.000(3) C14 0.025(4) 0.024(3) 0.026(2) -0.006(2) 0.002(2) 0.000(3) C15 0.023(4) 0.025(2) 0.026(2) 0.000(2) -0.002(2) 0.002(3) O16 0.027(5) 0.027(3) 0.041(3) 0.000(3) -0.006(3) -0.010(3) O17 0.037(5) 0.031(3) 0.032(3) -0.006(3) -0.002(3) -0.001(4) H18 0.063(10) 0.031(6) 0.074(8) -0.002(6) 0.006(7) -0.015(6) H19 0.031(9) 0.062(7) 0.074(9) 0.009(6) 0.024(6) -0.022(7) H20 0.057(10) 0.055(8) 0.047(7) 0.003(6) 0.014(6) 0.002(7) H21 0.050(11) 0.057(8) 0.060(7) -0.015(7) 0.012(6) -0.019(7) H22 0.062(10) 0.054(7) 0.035(6) -0.003(5) 0.019(6) -0.037(7) H23 0.061(10) 0.041(7) 0.055(7) -0.021(6) 0.002(7) -0.002(6) H24 0.054(10) 0.070(8) 0.059(7) -0.031(6) 0.012(7) -0.005(8) H25 0.065(11) 0.075(9) 0.055(7) 0.008(6) 0.033(7) -0.004(9) H26 0.086(13) 0.043(7) 0.063(8) -0.009(6) 0.017(8) -0.006(8) H27 0.073(12) 0.039(6) 0.052(7) -0.005(6) 0.027(7) 0.010(7) H28 0.077(11) 0.034(6) 0.055(7) -0.003(5) 0.020(7) -0.024(7) H29 0.049(11) 0.039(7) 0.094(12) 0.000(7) -0.015(8) -0.013(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 C6 1.400(8) . ? C1 C2 1.404(8) . ? C1 C13 1.482(7) . ? C2 C3 1.402(8) . ? C2 H18 1.088(15) . ? C3 C4 1.395(9) . ? C3 H19 1.092(14) . ? C4 C5 1.389(8) . ? C4 H20 1.074(14) . ? C5 C6 1.391(8) . ? C5 H21 1.085(17) . ? C6 H22 1.091(13) . ? C7 C12 1.395(8) . ? C7 C8 1.414(7) . ? C7 C15 1.490(8) . ? C8 C9 1.382(9) . ? C8 H23 1.096(14) . ? C9 C10 1.386(8) . ? C9 H24 1.087(14) . ? C10 C11 1.396(8) . ? C10 H25 1.119(16) . ? C11 C12 1.389(8) . ? C11 H26 1.084(16) . ? C12 H27 1.080(14) . ? C13 O16 1.260(8) . ? C13 C14 1.440(8) . ? C14 C15 1.384(7) . ? C14 H28 1.061(15) . ? C15 O17 1.322(9) . ? O16 H29 1.392(19) . ? O17 H29 1.10(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 C6 C1 C2 118.5(5) . . ? C6 C1 C13 122.6(4) . . ? C2 C1 C13 118.8(5) . . ? C3 C2 C1 120.2(5) . . ? C3 C2 H18 121.5(9) . . ? C1 C2 H18 118.4(9) . . ? C2 C3 C4 120.7(5) . . ? C2 C3 H19 120.0(9) . . ? C4 C3 H19 119.2(9) . . ? C5 C4 C3 119.0(5) . . ? C5 C4 H20 121.6(9) . . ? C3 C4 H20 119.4(9) . . ? C6 C5 C4 120.7(5) . . ? C6 C5 H21 118.7(8) . . ? C4 C5 H21 120.6(8) . . ? C5 C6 C1 121.0(5) . . ? C5 C6 H22 118.6(7) . . ? C1 C6 H22 120.5(7) . . ? C12 C7 C8 119.3(5) . . ? C12 C7 C15 122.3(5) . . ? C8 C7 C15 118.4(5) . . ? C9 C8 C7 120.2(5) . . ? C9 C8 H23 121.4(8) . . ? C7 C8 H23 118.5(8) . . ? C8 C9 C10 119.9(5) . . ? C8 C9 H24 121.0(10) . . ? C10 C9 H24 119.1(10) . . ? C9 C10 C11 120.6(5) . . ? C9 C10 H25 120.2(9) . . ? C11 C10 H25 119.2(9) . . ? C12 C11 C10 119.9(5) . . ? C12 C11 H26 120.2(9) . . ? C10 C11 H26 119.9(9) . . ? C11 C12 C7 120.2(5) . . ? C11 C12 H27 119.7(9) . . ? C7 C12 H27 120.1(9) . . ? O16 C13 C14 121.2(5) . . ? O16 C13 C1 117.7(5) . . ? C14 C13 C1 121.2(5) . . ? C15 C14 C13 118.5(5) . . ? C15 C14 H28 120.6(8) . . ? C13 C14 H28 120.9(8) . . ? O17 C15 C14 120.9(5) . . ? O17 C15 C7 116.3(5) . . ? C14 C15 C7 122.9(5) . . ? C13 O16 H29 100.9(7) . . ? C15 O17 H29 102.5(8) . . ? 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 C6 C1 C2 C3 -1.7(8) . . . . ? C13 C1 C2 C3 -178.0(5) . . . . ? C1 C2 C3 C4 0.7(9) . . . . ? C2 C3 C4 C5 0.8(9) . . . . ? C3 C4 C5 C6 -1.2(9) . . . . ? C4 C5 C6 C1 0.2(9) . . . . ? C2 C1 C6 C5 1.3(8) . . . . ? C13 C1 C6 C5 177.4(5) . . . . ? C12 C7 C8 C9 0.4(9) . . . . ? C15 C7 C8 C9 179.7(5) . . . . ? C7 C8 C9 C10 -1.1(9) . . . . ? C8 C9 C10 C11 0.6(10) . . . . ? C9 C10 C11 C12 0.5(10) . . . . ? C10 C11 C12 C7 -1.2(9) . . . . ? C8 C7 C12 C11 0.7(8) . . . . ? C15 C7 C12 C11 -178.5(5) . . . . ? C6 C1 C13 O16 -176.5(6) . . . . ? C2 C1 C13 O16 -0.4(8) . . . . ? C6 C1 C13 C14 4.4(8) . . . . ? C2 C1 C13 C14 -179.5(5) . . . . ? O16 C13 C14 C15 4.2(8) . . . . ? C1 C13 C14 C15 -176.7(5) . . . . ? C13 C14 C15 O17 -1.4(8) . . . . ? C13 C14 C15 C7 179.2(5) . . . . ? C12 C7 C15 O17 161.5(6) . . . . ? C8 C7 C15 O17 -17.8(8) . . . . ? C12 C7 C15 C14 -19.1(8) . . . . ? C8 C7 C15 C14 161.7(5) . . . . ? _refine_diff_density_max 0.093 _refine_diff_density_min -0.087 _refine_diff_density_rms 0.020 data_dbm240 _database_code_depnum_ccdc_archive 'CCDC 739590' _audit_creation_method SHELXL-97 _chemical_name_systematic ; dibenzoylmethane ; _chemical_name_common dibenzoylmethane _chemical_melting_point ? _chemical_formula_moiety 'C15 O2 H12' _chemical_formula_sum 'C15 H12 O2' _chemical_formula_weight 224.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 6.646 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H -3.739 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 5.803 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 8.723(3) _cell_length_b 10.7969(12) _cell_length_c 24.4233(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2300.2(8) _cell_formula_units_Z 8 _cell_measurement_temperature 240(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 2.5 _exptl_crystal_size_mid 2.0 _exptl_crystal_size_min 1.5 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 53 _exptl_absorpt_coefficient_mu '1.72, at 1 Angstrom' _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.513 _exptl_absorpt_correction_T_max 0.773 _exptl_absorpt_process_details ; The linear absorption coefficient is wavelength dependent and it is calculated as: mu = 0.89 + 0.83 * lambda [cm^-1] ; _exptl_special_details ; For peak integration a local UB matrix refined for each frame, using approximately 25 reflections. Hence _cell_measurement_reflns_used 25 For final cell dimensions an average of all local cells was performed and estimated standard uncertainties were obtained from the spread of the local observations Because of the nature of the experiment, it is not possible to give values of theta_min and theta_max for the cell determination. Instead, we can give values of _cell_measurement_sin(theta)/lambda_min 0.10 _cell_measurement_sin(theta)/lambda_max 0.70 The same applies for the wavelength used for the experiment. The range of wavelengths used was 0.5-5.0 Angstroms, BUT the bulk of the diffraction information is obtained from wavelengths in the range 0.7-2.5 Angstroms. ; _diffrn_ambient_temperature 240(2) _diffrn_radiation_wavelength 0.5-5.0 _diffrn_radiation_type neutron _diffrn_radiation_source 'ISIS spallation source' _diffrn_radiation_monochromator none _diffrn_measurement_device SXD _diffrn_measurement_method 'time of flight LAUE diffraction' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2592 _diffrn_reflns_av_R_equivalents 0.0700 _diffrn_reflns_av_sigmaI/netI 0.0570 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 14.14 _reflns_number_total 836 _reflns_number_gt 836 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; The variable wavelength nature of the data collection procedure means that sensible values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max cannot be given It is also difficult to estimate realistic values of maximum sin(theta)/lambda values for two reasons: (i) Different sin(theta)/lambda ranges are accessed in different parts of the detectors (ii) The nature of the data collection occasionally allows some reflections at very high sin(theta)/lambda to be observed even when no real attempt has been made to measure data in this region. However, we can attempt to estimate the sin(theta)/lambda limits as follows: _diffrn_reflns_sin(theta)/lambda_min 0.10 _diffrn_reflns_sin(theta)/lambda_max 0.74 Note also that reflections for which the standard profile fitting integration procedure fails are excluded from the data set, thus resulting in a high elimination rate of very weak or "unobserved" peaks from the final data set. The extinction coefficient reported in _refine_ls_extinction_coef is in this case the refined value of the mosaic spread in units of 10^-4 rad^-1 The reference for the extinction method used is: Becker, P. & Coppens, P. (1974). Acta Cryst. A30, 129-148. ; _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method 'Becker-Coppens Lorentzian model' _refine_ls_extinction_coef 0.165 _refine_ls_number_reflns 836 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0761 _refine_ls_R_factor_gt 0.0761 _refine_ls_wR_factor_ref 0.1539 _refine_ls_wR_factor_gt 0.1539 _refine_ls_goodness_of_fit_ref 1.502 _refine_ls_restrained_S_all 1.502 _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 C1 C 0.1876(8) 0.9445(6) 0.5199(2) 0.0337(16) Uani 1 1 d . . . C2 C 0.0826(9) 0.8790(7) 0.5527(3) 0.0412(18) Uani 1 1 d . . . C3 C 0.0404(10) 0.9268(7) 0.6038(3) 0.049(2) Uani 1 1 d . . . C4 C 0.0989(9) 1.0389(7) 0.6219(3) 0.0431(18) Uani 1 1 d . . . C5 C 0.2006(9) 1.1039(7) 0.5892(3) 0.0433(18) Uani 1 1 d . . . C6 C 0.2439(9) 1.0577(6) 0.5389(2) 0.0380(16) Uani 1 1 d . . . C7 C 0.4701(8) 0.9649(6) 0.3388(2) 0.0340(16) Uani 1 1 d . . . C8 C 0.5237(9) 0.8927(7) 0.2949(3) 0.0422(17) Uani 1 1 d . . . C9 C 0.6240(10) 0.9425(7) 0.2569(3) 0.0484(18) Uani 1 1 d . . . C10 C 0.6680(10) 1.0663(7) 0.2615(3) 0.051(2) Uani 1 1 d . . . C11 C 0.6187(9) 1.1380(7) 0.3047(3) 0.0462(19) Uani 1 1 d . . . C12 C 0.5184(8) 1.0876(6) 0.3435(3) 0.0415(17) Uani 1 1 d . . . C13 C 0.2294(8) 0.8944(6) 0.4651(3) 0.0348(16) Uani 1 1 d . . . C14 C 0.3341(9) 0.9546(6) 0.4301(2) 0.0350(16) Uani 1 1 d . . . C15 C 0.3624(9) 0.9065(6) 0.3785(2) 0.0353(16) Uani 1 1 d . . . O16 O 0.1644(10) 0.7934(7) 0.4513(3) 0.044(2) Uani 1 1 d . . . O17 O 0.2977(12) 0.8049(7) 0.3620(3) 0.048(2) Uani 1 1 d . . . H18 H 0.036(2) 0.7930(16) 0.5367(7) 0.070(4) Uani 1 1 d . . . H19 H -0.037(2) 0.8756(16) 0.6297(7) 0.074(5) Uani 1 1 d . . . H20 H 0.0647(18) 1.0737(15) 0.6615(6) 0.069(5) Uani 1 1 d . . . H21 H 0.2435(19) 1.1939(15) 0.6027(6) 0.072(5) Uani 1 1 d . . . H22 H 0.321(2) 1.1117(14) 0.5134(5) 0.068(5) Uani 1 1 d . . . H23 H 0.490(2) 0.7947(14) 0.2913(6) 0.070(4) Uani 1 1 d . . . H24 H 0.674(2) 0.8867(18) 0.2234(7) 0.087(6) Uani 1 1 d . . . H25 H 0.751(2) 1.1065(18) 0.2309(7) 0.090(6) Uani 1 1 d . . . H26 H 0.651(3) 1.2344(15) 0.3091(6) 0.086(6) Uani 1 1 d . . . H27 H 0.480(2) 1.1427(13) 0.3769(7) 0.064(4) Uani 1 1 d . . . H28 H 0.386(2) 1.0395(14) 0.4435(6) 0.066(4) Uani 1 1 d . . . H29 H 0.225(2) 0.7775(14) 0.3987(8) 0.071(5) 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 0.028(4) 0.037(4) 0.037(3) 0.009(3) -0.001(3) 0.006(3) C2 0.036(5) 0.037(4) 0.051(4) 0.011(3) 0.007(3) -0.007(3) C3 0.048(6) 0.053(5) 0.046(4) 0.017(4) 0.012(4) 0.002(4) C4 0.039(5) 0.044(4) 0.047(4) 0.007(3) 0.003(4) 0.003(4) C5 0.045(5) 0.043(4) 0.041(4) -0.004(3) 0.005(3) -0.011(4) C6 0.033(5) 0.042(4) 0.039(3) 0.004(3) 0.003(3) -0.010(3) C7 0.026(4) 0.035(4) 0.041(4) 0.001(3) -0.004(3) 0.011(3) C8 0.045(5) 0.042(4) 0.040(4) -0.009(3) -0.006(3) 0.010(4) C9 0.050(5) 0.059(5) 0.036(4) -0.012(3) 0.010(4) 0.001(4) C10 0.046(6) 0.065(5) 0.041(4) -0.002(3) 0.015(3) 0.008(4) C11 0.045(5) 0.045(4) 0.049(4) 0.005(3) 0.007(4) -0.005(4) C12 0.045(5) 0.036(4) 0.043(4) -0.005(3) 0.005(3) 0.003(4) C13 0.029(5) 0.033(3) 0.043(3) 0.005(3) -0.008(3) 0.005(3) C14 0.032(5) 0.035(4) 0.038(3) -0.002(3) 0.002(3) -0.004(4) C15 0.034(5) 0.037(3) 0.035(3) -0.001(3) -0.009(3) -0.002(3) O16 0.039(6) 0.039(4) 0.054(5) 0.002(4) -0.003(4) -0.007(4) O17 0.056(7) 0.043(4) 0.044(4) 0.000(4) -0.003(4) 0.001(5) H18 0.057(12) 0.053(9) 0.099(12) 0.004(9) 0.015(8) -0.012(8) H19 0.054(12) 0.089(11) 0.078(10) 0.007(9) 0.030(8) -0.027(9) H20 0.066(12) 0.076(11) 0.067(10) 0.014(8) 0.030(8) 0.008(9) H21 0.074(13) 0.067(10) 0.073(9) -0.019(9) 0.019(9) -0.026(9) H22 0.088(13) 0.063(9) 0.053(8) 0.002(7) 0.021(8) -0.046(9) H23 0.082(14) 0.057(10) 0.071(9) -0.018(8) 0.010(9) 0.000(9) H24 0.091(15) 0.095(12) 0.076(10) -0.034(10) 0.024(10) -0.005(11) H25 0.086(14) 0.108(14) 0.077(10) 0.012(9) 0.035(10) -0.028(12) H26 0.121(19) 0.055(10) 0.082(11) -0.011(8) 0.033(10) -0.011(10) H27 0.067(13) 0.051(8) 0.075(10) -0.010(7) 0.019(8) 0.012(8) H28 0.084(13) 0.045(8) 0.069(8) -0.012(7) 0.019(8) -0.019(8) H29 0.052(13) 0.061(9) 0.100(13) -0.007(9) -0.010(9) -0.017(8) _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 C6 1.397(9) . ? C1 C2 1.409(10) . ? C1 C13 1.488(9) . ? C2 C3 1.398(10) . ? C2 H18 1.09(2) . ? C3 C4 1.386(11) . ? C3 H19 1.08(2) . ? C4 C5 1.385(10) . ? C4 H20 1.08(2) . ? C5 C6 1.379(9) . ? C5 H21 1.09(2) . ? C6 H22 1.086(17) . ? C7 C8 1.405(9) . ? C7 C12 1.394(9) . ? C7 C15 1.491(10) . ? C8 C9 1.384(10) . ? C8 H23 1.10(2) . ? C9 C10 1.395(11) . ? C9 H24 1.11(2) . ? C10 C11 1.378(10) . ? C10 H25 1.12(2) . ? C11 C12 1.400(10) . ? C11 H26 1.09(2) . ? C12 H27 1.064(19) . ? C13 O16 1.275(10) . ? C13 C14 1.410(10) . ? C14 C15 1.385(8) . ? C14 H28 1.07(2) . ? C15 O17 1.297(10) . ? O16 H29 1.40(2) . ? O17 H29 1.14(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 C6 C1 C2 118.6(6) . . ? C6 C1 C13 122.0(5) . . ? C2 C1 C13 119.3(6) . . ? C3 C2 C1 119.6(7) . . ? C3 C2 H18 122.7(10) . . ? C1 C2 H18 117.7(10) . . ? C2 C3 C4 120.7(7) . . ? C2 C3 H19 119.9(11) . . ? C4 C3 H19 119.4(11) . . ? C5 C4 C3 119.6(7) . . ? C5 C4 H20 121.1(11) . . ? C3 C4 H20 119.2(11) . . ? C6 C5 C4 120.4(7) . . ? C6 C5 H21 119.8(9) . . ? C4 C5 H21 119.8(9) . . ? C5 C6 C1 121.1(6) . . ? C5 C6 H22 119.1(9) . . ? C1 C6 H22 119.8(9) . . ? C8 C7 C12 119.4(7) . . ? C8 C7 C15 118.1(6) . . ? C12 C7 C15 122.6(6) . . ? C9 C8 C7 120.4(7) . . ? C9 C8 H23 119.1(10) . . ? C7 C8 H23 120.5(10) . . ? C8 C9 C10 119.6(6) . . ? C8 C9 H24 122.3(13) . . ? C10 C9 H24 118.1(12) . . ? C11 C10 C9 120.9(7) . . ? C11 C10 H25 119.4(12) . . ? C9 C10 H25 119.6(12) . . ? C12 C11 C10 119.7(7) . . ? C12 C11 H26 118.1(11) . . ? C10 C11 H26 122.1(11) . . ? C11 C12 C7 120.1(6) . . ? C11 C12 H27 119.9(11) . . ? C7 C12 H27 120.0(11) . . ? O16 C13 C14 121.5(6) . . ? O16 C13 C1 116.0(6) . . ? C14 C13 C1 122.5(6) . . ? C15 C14 C13 119.6(6) . . ? C15 C14 H28 121.4(10) . . ? C13 C14 H28 118.9(9) . . ? O17 C15 C14 121.5(7) . . ? O17 C15 C7 115.4(6) . . ? C14 C15 C7 123.0(6) . . ? C13 O16 H29 100.4(8) . . ? C15 O17 H29 102.6(9) . . ? 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 C6 C1 C2 C3 -1.5(10) . . . . ? C13 C1 C2 C3 -178.7(6) . . . . ? C1 C2 C3 C4 1.1(11) . . . . ? C2 C3 C4 C5 -0.3(11) . . . . ? C3 C4 C5 C6 0.0(11) . . . . ? C4 C5 C6 C1 -0.4(11) . . . . ? C2 C1 C6 C5 1.2(10) . . . . ? C13 C1 C6 C5 178.3(6) . . . . ? C12 C7 C8 C9 0.2(10) . . . . ? C15 C7 C8 C9 180.0(6) . . . . ? C7 C8 C9 C10 -1.9(11) . . . . ? C8 C9 C10 C11 3.0(12) . . . . ? C9 C10 C11 C12 -2.4(12) . . . . ? C10 C11 C12 C7 0.7(11) . . . . ? C8 C7 C12 C11 0.4(10) . . . . ? C15 C7 C12 C11 -179.4(7) . . . . ? C6 C1 C13 O16 -176.5(7) . . . . ? C2 C1 C13 O16 0.5(10) . . . . ? C6 C1 C13 C14 3.2(10) . . . . ? C2 C1 C13 C14 -179.7(6) . . . . ? O16 C13 C14 C15 3.0(10) . . . . ? C1 C13 C14 C15 -176.7(6) . . . . ? C13 C14 C15 O17 -1.9(10) . . . . ? C13 C14 C15 C7 179.4(6) . . . . ? C8 C7 C15 O17 -16.5(9) . . . . ? C12 C7 C15 O17 163.2(7) . . . . ? C8 C7 C15 C14 162.2(6) . . . . ? C12 C7 C15 C14 -18.1(10) . . . . ? _refine_diff_density_max 0.074 _refine_diff_density_min -0.069 _refine_diff_density_rms 0.018 data_dbm280 _database_code_depnum_ccdc_archive 'CCDC 739591' _audit_creation_method SHELXL-97 _chemical_name_systematic ; dibenzoylmethane ; _chemical_name_common dibenzoylmethane _chemical_melting_point ? _chemical_formula_moiety 'C15 O2 H12' _chemical_formula_sum 'C15 H12 O2' _chemical_formula_weight 224.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 6.646 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H -3.739 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 5.803 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 8.7652(8) _cell_length_b 10.8627(9) _cell_length_c 24.513(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2334.0(4) _cell_formula_units_Z 8 _cell_measurement_temperature 280(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 2.5 _exptl_crystal_size_mid 2.0 _exptl_crystal_size_min 1.5 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 53 _exptl_absorpt_coefficient_mu '1.72, at 1 Angstrom' _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.513 _exptl_absorpt_correction_T_max 0.773 _exptl_absorpt_process_details ; The linear absorption coefficient is wavelength dependent and it is calculated as: mu = 0.89 + 0.83 * lambda [cm^-1] ; _exptl_special_details ; For peak integration a local UB matrix refined for each frame, using approximately 25 reflections. Hence _cell_measurement_reflns_used 25 For final cell dimensions an average of all local cells was performed and estimated standard uncertainties were obtained from the spread of the local observations Because of the nature of the experiment, it is not possible to give values of theta_min and theta_max for the cell determination. Instead, we can give values of _cell_measurement_sin(theta)/lambda_min 0.10 _cell_measurement_sin(theta)/lambda_max 0.70 The same applies for the wavelength used for the experiment. The range of wavelengths used was 0.5-5.0 Angstroms, BUT the bulk of the diffraction information is obtained from wavelengths in the range 0.7-2.5 Angstroms. ; _diffrn_ambient_temperature 280(2) _diffrn_radiation_wavelength 0.5-5.0 _diffrn_radiation_type neutron _diffrn_radiation_source 'ISIS spallation source' _diffrn_radiation_monochromator none _diffrn_measurement_device SXD _diffrn_measurement_method 'time of flight LAUE diffraction' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1768 _diffrn_reflns_av_R_equivalents 0.071 _diffrn_reflns_av_sigmaI/netI 0.0566 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 11.81 _reflns_number_total 680 _reflns_number_gt 680 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; The variable wavelength nature of the data collection procedure means that sensible values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max cannot be given It is also difficult to estimate realistic values of maximum sin(theta)/lambda values for two reasons: (i) Different sin(theta)/lambda ranges are accessed in different parts of the detectors (ii) The nature of the data collection occasionally allows some reflections at very high sin(theta)/lambda to be observed even when no real attempt has been made to measure data in this region. However, we can attempt to estimate the sin(theta)/lambda limits as follows: _diffrn_reflns_sin(theta)/lambda_min 0.10 _diffrn_reflns_sin(theta)/lambda_max 0.70 Note also that reflections for which the standard profile fitting integration procedure fails are excluded from the data set, thus resulting in a high elimination rate of very weak or "unobserved" peaks from the final data set. The extinction coefficient reported in _refine_ls_extinction_coef is in this case the refined value of the mosaic spread in units of 10^-4 rad^-1 The reference for the extinction method used is: Becker, P. & Coppens, P. (1974). Acta Cryst. A30, 129-148. ; _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method 'Becker-Coppens Lorentzian model' _refine_ls_extinction_coef 0.165 _refine_ls_number_reflns 680 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0670 _refine_ls_R_factor_gt 0.0670 _refine_ls_wR_factor_ref 0.1284 _refine_ls_wR_factor_gt 0.1284 _refine_ls_goodness_of_fit_ref 1.318 _refine_ls_restrained_S_all 1.318 _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 C1 C 0.1889(8) 0.9437(6) 0.5188(3) 0.0427(19) Uani 1 1 d . . . C2 C 0.0816(9) 0.8795(7) 0.5518(3) 0.050(2) Uani 1 1 d . . . C3 C 0.0410(10) 0.9254(8) 0.6027(4) 0.059(2) Uani 1 1 d . . . C4 C 0.1003(10) 1.0350(8) 0.6210(3) 0.049(2) Uani 1 1 d . . . C5 C 0.1995(11) 1.1004(9) 0.5885(3) 0.058(2) Uani 1 1 d . . . C6 C 0.2431(10) 1.0562(7) 0.5383(3) 0.050(2) Uani 1 1 d . . . C7 C 0.4711(9) 0.9667(7) 0.3386(2) 0.043(2) Uani 1 1 d . . . C8 C 0.5236(11) 0.8934(9) 0.2945(3) 0.056(2) Uani 1 1 d . . . C9 C 0.6228(11) 0.9449(9) 0.2568(3) 0.060(3) Uani 1 1 d . . . C10 C 0.6671(12) 1.0696(9) 0.2623(3) 0.067(3) Uani 1 1 d . . . C11 C 0.6163(11) 1.1401(9) 0.3055(3) 0.060(2) Uani 1 1 d . . . C12 C 0.5183(9) 1.0883(7) 0.3432(3) 0.047(2) Uani 1 1 d . . . C13 C 0.2296(9) 0.8946(6) 0.4648(3) 0.046(2) Uani 1 1 d . . . C14 C 0.3335(10) 0.9548(7) 0.4301(3) 0.0405(18) Uani 1 1 d . . . C15 C 0.3636(9) 0.9069(6) 0.3783(3) 0.045(2) Uani 1 1 d . . . O16 O 0.1685(12) 0.7931(7) 0.4502(4) 0.056(3) Uani 1 1 d . . . O17 O 0.2986(13) 0.8058(8) 0.3611(4) 0.057(3) Uani 1 1 d . . . H18 H 0.041(2) 0.7899(17) 0.5364(8) 0.086(5) Uani 1 1 d . . . H19 H -0.035(2) 0.872(2) 0.6274(9) 0.097(7) Uani 1 1 d . . . H20 H 0.066(2) 1.0716(17) 0.6613(7) 0.083(6) Uani 1 1 d . . . H21 H 0.244(2) 1.1898(19) 0.6021(7) 0.092(6) Uani 1 1 d . . . H22 H 0.322(2) 1.1109(16) 0.5129(6) 0.084(6) Uani 1 1 d . . . H23 H 0.493(2) 0.8011(18) 0.2913(7) 0.079(5) Uani 1 1 d . . . H24 H 0.674(2) 0.889(2) 0.2230(7) 0.101(7) Uani 1 1 d . . . H25 H 0.747(3) 1.110(2) 0.2306(8) 0.102(6) Uani 1 1 d . . . H26 H 0.646(3) 1.2365(18) 0.3089(8) 0.093(6) Uani 1 1 d . . . H27 H 0.475(2) 1.1437(15) 0.3783(8) 0.084(6) Uani 1 1 d . . . H28 H 0.389(2) 1.0378(17) 0.4429(7) 0.078(5) Uani 1 1 d . . . H29 H 0.229(3) 0.7779(16) 0.3981(10) 0.094(6) 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 0.030(4) 0.044(4) 0.054(4) 0.010(3) -0.001(3) 0.002(4) C2 0.041(6) 0.042(4) 0.068(5) 0.003(4) 0.008(4) -0.007(4) C3 0.049(7) 0.062(6) 0.064(6) 0.015(5) 0.006(4) -0.002(5) C4 0.034(5) 0.064(5) 0.050(5) 0.011(4) 0.008(4) 0.007(4) C5 0.060(6) 0.060(5) 0.053(5) 0.000(4) 0.005(4) -0.011(5) C6 0.050(6) 0.050(5) 0.050(4) 0.000(4) -0.001(4) -0.012(4) C7 0.043(6) 0.043(4) 0.041(4) 0.003(4) -0.005(4) 0.003(4) C8 0.065(6) 0.060(5) 0.044(4) -0.014(5) 0.003(4) 0.003(5) C9 0.056(7) 0.076(7) 0.048(5) -0.018(5) 0.005(4) 0.009(5) C10 0.059(7) 0.083(7) 0.059(5) 0.009(5) 0.013(5) 0.009(6) C11 0.065(7) 0.054(5) 0.060(5) 0.002(5) 0.020(5) 0.006(5) C12 0.049(5) 0.044(4) 0.048(4) -0.006(4) 0.010(4) 0.003(4) C13 0.046(6) 0.038(4) 0.052(4) 0.009(4) -0.010(4) 0.000(4) C14 0.038(5) 0.036(4) 0.048(4) -0.008(4) 0.000(3) 0.000(4) C15 0.040(6) 0.044(4) 0.052(4) -0.003(4) -0.008(3) 0.005(4) O16 0.054(7) 0.052(5) 0.063(6) 0.004(5) -0.006(5) -0.012(5) O17 0.070(8) 0.047(5) 0.054(5) -0.004(5) -0.008(5) -0.002(6) H18 0.068(13) 0.064(11) 0.127(14) -0.001(11) 0.034(10) -0.035(9) H19 0.075(15) 0.106(14) 0.110(15) 0.027(12) 0.038(11) -0.019(12) H20 0.080(15) 0.101(15) 0.069(11) 0.006(11) 0.024(9) -0.003(11) H21 0.110(19) 0.083(12) 0.083(10) -0.025(11) 0.026(11) -0.037(12) H22 0.102(14) 0.081(11) 0.069(9) -0.014(9) 0.052(10) -0.048(11) H23 0.083(14) 0.070(12) 0.083(11) -0.019(10) -0.004(10) 0.015(11) H24 0.071(14) 0.151(18) 0.081(10) -0.042(13) 0.020(10) -0.001(13) H25 0.088(14) 0.125(15) 0.093(11) 0.016(11) 0.048(11) -0.006(13) H26 0.099(19) 0.078(13) 0.101(14) -0.013(11) 0.026(12) -0.007(12) H27 0.107(17) 0.053(8) 0.091(12) -0.018(8) 0.034(11) 0.010(10) H28 0.093(16) 0.064(10) 0.077(10) -0.008(9) 0.028(9) -0.032(11) H29 0.100(19) 0.068(11) 0.113(16) -0.006(12) -0.004(14) -0.015(11) _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 C6 1.396(10) . ? C1 C2 1.424(10) . ? C1 C13 1.471(10) . ? C2 C3 1.390(11) . ? C2 H18 1.10(2) . ? C3 C4 1.375(11) . ? C3 H19 1.07(3) . ? C4 C5 1.376(12) . ? C4 H20 1.10(2) . ? C5 C6 1.375(11) . ? C5 H21 1.10(3) . ? C6 H22 1.11(2) . ? C7 C8 1.420(11) . ? C7 C12 1.388(10) . ? C7 C15 1.503(11) . ? C8 C9 1.385(12) . ? C8 H23 1.04(3) . ? C9 C10 1.415(14) . ? C9 H24 1.12(2) . ? C10 C11 1.380(12) . ? C10 H25 1.13(3) . ? C11 C12 1.381(11) . ? C11 H26 1.08(3) . ? C12 H27 1.12(2) . ? C13 O16 1.277(11) . ? C13 C14 1.408(11) . ? C14 C15 1.396(9) . ? C14 H28 1.07(2) . ? C15 O17 1.308(11) . ? O16 H29 1.39(3) . ? O17 H29 1.13(3) . ? 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 C6 C1 C2 117.4(6) . . ? C6 C1 C13 122.9(6) . . ? C2 C1 C13 119.6(7) . . ? C3 C2 C1 120.2(8) . . ? C3 C2 H18 122.8(12) . . ? C1 C2 H18 116.8(11) . . ? C2 C3 C4 120.5(8) . . ? C2 C3 H19 118.4(15) . . ? C4 C3 H19 121.1(14) . . ? C5 C4 C3 119.8(8) . . ? C5 C4 H20 120.1(13) . . ? C3 C4 H20 120.1(12) . . ? C6 C5 C4 120.9(9) . . ? C6 C5 H21 118.7(10) . . ? C4 C5 H21 120.3(11) . . ? C5 C6 C1 121.1(8) . . ? C5 C6 H22 119.5(11) . . ? C1 C6 H22 119.4(10) . . ? C8 C7 C12 119.9(7) . . ? C8 C7 C15 117.0(7) . . ? C12 C7 C15 123.1(6) . . ? C9 C8 C7 119.0(9) . . ? C9 C8 H23 120.2(12) . . ? C7 C8 H23 120.8(12) . . ? C8 C9 C10 119.7(8) . . ? C8 C9 H24 121.5(15) . . ? C10 C9 H24 118.7(14) . . ? C11 C10 C9 121.0(9) . . ? C11 C10 H25 120.7(15) . . ? C9 C10 H25 118.3(14) . . ? C12 C11 C10 119.2(9) . . ? C12 C11 H26 119.5(12) . . ? C10 C11 H26 121.3(13) . . ? C11 C12 C7 121.2(7) . . ? C11 C12 H27 120.5(12) . . ? C7 C12 H27 118.3(11) . . ? O16 C13 C14 120.2(7) . . ? O16 C13 C1 117.7(7) . . ? C14 C13 C1 122.2(6) . . ? C15 C14 C13 119.9(7) . . ? C15 C14 H28 119.6(10) . . ? C13 C14 H28 120.5(10) . . ? O17 C15 C14 121.6(8) . . ? O17 C15 C7 115.3(7) . . ? C14 C15 C7 123.1(7) . . ? C13 O16 H29 101.6(10) . . ? C15 O17 H29 101.6(11) . . ? 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 C6 C1 C2 C3 -3.6(11) . . . . ? C13 C1 C2 C3 -179.4(7) . . . . ? C1 C2 C3 C4 2.0(12) . . . . ? C2 C3 C4 C5 0.6(12) . . . . ? C3 C4 C5 C6 -1.5(13) . . . . ? C4 C5 C6 C1 -0.3(12) . . . . ? C2 C1 C6 C5 2.8(11) . . . . ? C13 C1 C6 C5 178.4(7) . . . . ? C12 C7 C8 C9 0.6(12) . . . . ? C15 C7 C8 C9 179.9(7) . . . . ? C7 C8 C9 C10 -1.4(13) . . . . ? C8 C9 C10 C11 1.7(14) . . . . ? C9 C10 C11 C12 -1.3(14) . . . . ? C10 C11 C12 C7 0.5(13) . . . . ? C8 C7 C12 C11 -0.1(12) . . . . ? C15 C7 C12 C11 -179.4(8) . . . . ? C6 C1 C13 O16 -177.2(8) . . . . ? C2 C1 C13 O16 -1.6(11) . . . . ? C6 C1 C13 C14 3.6(11) . . . . ? C2 C1 C13 C14 179.2(7) . . . . ? O16 C13 C14 C15 3.4(11) . . . . ? C1 C13 C14 C15 -177.4(6) . . . . ? C13 C14 C15 O17 -0.7(11) . . . . ? C13 C14 C15 C7 179.1(7) . . . . ? C8 C7 C15 O17 -16.9(10) . . . . ? C12 C7 C15 O17 162.3(8) . . . . ? C8 C7 C15 C14 163.2(7) . . . . ? C12 C7 C15 C14 -17.5(11) . . . . ? _refine_diff_density_max 0.062 _refine_diff_density_min -0.048 _refine_diff_density_rms 0.012 # Attachment 'B908915B_dbm_xray_ccdc3.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2009-03-28 at 16:59:17 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.4 # Request file : c:\wingx\files\archive.reqdat # CIF files read : dbm100_cu #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_dbm100_cu _database_code_depnum_ccdc_archive 'CCDC 739592' _audit_creation_date 2009-03-28T16:59:17-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; dibenzoylmethane ; _chemical_formula_sum 'C15 H12 O2' _chemical_formula_weight 224.25 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 8.6251(5) _cell_length_b 10.6442(8) _cell_length_c 24.3193(16) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2232.7(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ; ? ; _exptl_crystal_description block _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_colour white #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.704 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _cell_measurement_reflns_used 262 _cell_measurement_theta_min 28.97 _cell_measurement_theta_max 116.77 _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54186 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; 'Rigaku R-AXIS RAPID IP Image Plate diffractometer' ; _diffrn_measurement_method \w _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_unetI/netI 0.0182 _diffrn_reflns_number 8999 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 6.85 _diffrn_reflns_theta_max 71.57 _diffrn_reflns_theta_full 71.57 _diffrn_measured_fraction_theta_full 0.955 _diffrn_measured_fraction_theta_max 0.955 _reflns_number_total 2083 _reflns_number_gt 1742 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Farrugia, 1997), Mercury (McRae, 2006)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0346P)^2^+0.6787P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_number_reflns 2083 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.1018 _refine_ls_wR_factor_gt 0.0924 _refine_ls_goodness_of_fit_ref 1.337 _refine_ls_restrained_S_all 1.337 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.211 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.047 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' 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 0.18407(17) 0.94708(14) 0.52229(6) 0.0181(3) Uani 1 1 d . . . C2 C 0.07784(18) 0.88169(15) 0.55556(6) 0.0211(4) Uani 1 1 d . . . C3 C 0.03503(19) 0.92993(15) 0.60641(7) 0.0226(4) Uani 1 1 d . . . C4 C 0.09657(19) 1.04358(15) 0.62457(6) 0.0223(4) Uani 1 1 d . . . C5 C 0.19993(18) 1.10958(16) 0.59151(6) 0.0224(4) Uani 1 1 d . . . C6 C 0.24399(18) 1.06150(15) 0.54084(6) 0.0197(3) Uani 1 1 d . . . C7 C 0.46991(17) 0.96163(14) 0.33942(6) 0.0177(3) Uani 1 1 d . . . C8 C 0.52301(18) 0.88683(16) 0.29565(6) 0.0211(4) Uani 1 1 d . . . C9 C 0.62530(19) 0.93571(15) 0.25704(6) 0.0231(4) Uani 1 1 d . . . C10 C 0.67432(19) 1.05962(16) 0.26108(7) 0.0248(4) Uani 1 1 d . . . C11 C 0.62234(19) 1.13512(16) 0.30423(7) 0.0234(4) Uani 1 1 d . . . C12 C 0.52141(18) 1.08601(15) 0.34345(6) 0.0203(4) Uani 1 1 d . . . C13 C 0.22535(17) 0.89454(14) 0.46751(6) 0.0190(3) Uani 1 1 d . . . C14 C 0.33350(18) 0.95495(15) 0.43177(6) 0.0193(3) Uani 1 1 d . . . C15 C 0.36111(17) 0.90582(14) 0.37985(6) 0.0184(3) Uani 1 1 d . . . O16 O 0.15941(13) 0.79217(10) 0.45267(4) 0.0233(3) Uani 1 1 d . . . O17 O 0.28971(13) 0.80289(10) 0.36334(4) 0.0231(3) Uani 1 1 d . . . H18 H 0.031(2) 0.8029(17) 0.5419(7) 0.027(5) Uiso 1 1 d . . . H19 H -0.039(2) 0.8834(16) 0.6301(7) 0.026(5) Uiso 1 1 d . . . H20 H 0.066(2) 1.0767(17) 0.6610(8) 0.033(5) Uiso 1 1 d . . . H21 H 0.243(2) 1.1921(17) 0.6043(7) 0.028(5) Uiso 1 1 d . . . H22 H 0.3147(18) 1.1124(15) 0.5176(7) 0.017(4) Uiso 1 1 d . . . H23 H 0.489(2) 0.7993(18) 0.2930(7) 0.029(5) Uiso 1 1 d . . . H24 H 0.6651(19) 0.8790(15) 0.2271(7) 0.024(4) Uiso 1 1 d . . . H25 H 0.746(2) 1.0952(16) 0.2337(7) 0.030(5) Uiso 1 1 d . . . H26 H 0.6558(19) 1.2265(17) 0.3075(7) 0.025(5) Uiso 1 1 d . . . H27 H 0.487(2) 1.1415(15) 0.3744(7) 0.022(4) Uiso 1 1 d . . . H28 H 0.388(2) 1.0336(16) 0.4440(7) 0.021(4) Uiso 1 1 d . . . H29 H 0.220(3) 0.779(2) 0.4025(10) 0.077(8) 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 C1 0.0176(7) 0.0192(8) 0.0176(8) 0.0033(6) -0.0019(6) 0.0025(6) C2 0.0189(8) 0.0210(9) 0.0233(8) 0.0032(6) -0.0007(6) 0.0004(6) C3 0.0207(8) 0.0249(9) 0.0221(8) 0.0083(6) 0.0031(6) 0.0014(6) C4 0.0229(8) 0.0258(9) 0.0182(8) 0.0013(6) 0.0019(6) 0.0026(7) C5 0.0231(8) 0.0239(9) 0.0201(8) 0.0003(6) -0.0011(6) -0.0013(7) C6 0.0194(8) 0.0214(9) 0.0183(8) 0.0040(6) -0.0004(6) -0.0002(6) C7 0.0169(7) 0.0190(8) 0.0171(8) 0.0010(6) -0.0029(6) 0.0027(6) C8 0.0229(8) 0.0207(9) 0.0197(8) -0.0029(6) -0.0046(6) 0.0028(6) C9 0.0250(8) 0.0259(9) 0.0185(8) -0.0046(6) -0.0008(6) 0.0050(6) C10 0.0233(8) 0.0333(10) 0.0177(8) 0.0035(7) 0.0016(6) 0.0020(7) C11 0.0264(9) 0.0207(9) 0.0231(9) 0.0007(6) 0.0004(6) 0.0017(7) C12 0.0212(8) 0.0223(9) 0.0174(8) -0.0010(6) 0.0005(6) 0.0040(6) C13 0.0181(8) 0.0180(9) 0.0208(8) 0.0026(6) -0.0051(6) 0.0034(6) C14 0.0210(8) 0.0176(9) 0.0193(8) 0.0010(6) -0.0007(6) 0.0003(6) C15 0.0180(8) 0.0160(8) 0.0210(8) 0.0024(6) -0.0044(6) 0.0024(6) O16 0.0272(6) 0.0219(7) 0.0209(6) 0.0008(4) -0.0018(4) -0.0037(5) O17 0.0281(6) 0.0193(6) 0.0218(6) -0.0020(4) -0.0014(4) -0.0030(5) _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 C6 1.398(2) . ? C1 C2 1.407(2) . ? C1 C13 1.488(2) . ? C2 C3 1.389(2) . ? C2 H18 0.989(18) . ? C3 C4 1.393(2) . ? C3 H19 0.995(18) . ? C4 C5 1.391(2) . ? C4 H20 0.988(18) . ? C5 C6 1.387(2) . ? C5 H21 1.003(18) . ? C6 H22 0.993(16) . ? C7 C12 1.400(2) . ? C7 C8 1.406(2) . ? C7 C15 1.483(2) . ? C8 C9 1.390(2) . ? C8 H23 0.980(19) . ? C9 C10 1.389(2) . ? C9 H24 1.006(17) . ? C10 C11 1.396(2) . ? C10 H25 0.983(19) . ? C11 C12 1.393(2) . ? C11 H26 1.018(18) . ? C12 H27 1.000(17) . ? C13 O16 1.2811(18) . ? C13 C14 1.428(2) . ? C14 C15 1.387(2) . ? C14 H28 1.005(17) . ? C15 O17 1.3193(18) . ? O16 H29 1.33(3) . ? O17 H29 1.16(3) . ? 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 C6 C1 C2 119.10(14) . . ? C6 C1 C13 121.87(14) . . ? C2 C1 C13 119.00(14) . . ? C3 C2 C1 120.16(15) . . ? C3 C2 H18 120.2(10) . . ? C1 C2 H18 119.6(10) . . ? C2 C3 C4 120.14(15) . . ? C2 C3 H19 120.2(10) . . ? C4 C3 H19 119.6(10) . . ? C5 C4 C3 119.97(15) . . ? C5 C4 H20 120.5(11) . . ? C3 C4 H20 119.6(11) . . ? C6 C5 C4 120.18(16) . . ? C6 C5 H21 119.9(10) . . ? C4 C5 H21 120.0(10) . . ? C5 C6 C1 120.45(15) . . ? C5 C6 H22 118.2(9) . . ? C1 C6 H22 121.2(9) . . ? C12 C7 C8 119.03(14) . . ? C12 C7 C15 122.21(14) . . ? C8 C7 C15 118.76(14) . . ? C9 C8 C7 120.42(15) . . ? C9 C8 H23 120.3(10) . . ? C7 C8 H23 119.3(10) . . ? C10 C9 C8 120.08(15) . . ? C10 C9 H24 121.2(10) . . ? C8 C9 H24 118.7(10) . . ? C9 C10 C11 120.16(15) . . ? C9 C10 H25 120.5(10) . . ? C11 C10 H25 119.3(10) . . ? C12 C11 C10 119.96(16) . . ? C12 C11 H26 118.8(10) . . ? C10 C11 H26 121.2(10) . . ? C11 C12 C7 120.35(14) . . ? C11 C12 H27 118.5(10) . . ? C7 C12 H27 121.2(10) . . ? O16 C13 C14 120.10(14) . . ? O16 C13 C1 117.76(14) . . ? C14 C13 C1 122.14(14) . . ? C15 C14 C13 119.76(15) . . ? C15 C14 H28 120.2(10) . . ? C13 C14 H28 120.0(9) . . ? O17 C15 C14 120.66(14) . . ? O17 C15 C7 115.22(13) . . ? C14 C15 C7 124.12(14) . . ? C13 O16 H29 99.9(11) . . ? C15 O17 H29 100.0(12) . . ? 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 C6 C1 C2 C3 -0.8(2) . . . . ? C13 C1 C2 C3 -178.74(14) . . . . ? C1 C2 C3 C4 0.3(2) . . . . ? C2 C3 C4 C5 0.6(2) . . . . ? C3 C4 C5 C6 -1.1(2) . . . . ? C4 C5 C6 C1 0.6(2) . . . . ? C2 C1 C6 C5 0.3(2) . . . . ? C13 C1 C6 C5 178.24(14) . . . . ? C12 C7 C8 C9 0.1(2) . . . . ? C15 C7 C8 C9 -179.84(14) . . . . ? C7 C8 C9 C10 -0.8(2) . . . . ? C8 C9 C10 C11 0.7(2) . . . . ? C9 C10 C11 C12 0.2(2) . . . . ? C10 C11 C12 C7 -0.9(2) . . . . ? C8 C7 C12 C11 0.8(2) . . . . ? C15 C7 C12 C11 -179.30(14) . . . . ? C6 C1 C13 O16 -176.72(13) . . . . ? C2 C1 C13 O16 1.2(2) . . . . ? C6 C1 C13 C14 2.8(2) . . . . ? C2 C1 C13 C14 -179.30(13) . . . . ? O16 C13 C14 C15 3.2(2) . . . . ? C1 C13 C14 C15 -176.29(13) . . . . ? C13 C14 C15 O17 -0.8(2) . . . . ? C13 C14 C15 C7 179.49(13) . . . . ? C12 C7 C15 O17 161.91(14) . . . . ? C8 C7 C15 O17 -18.1(2) . . . . ? C12 C7 C15 C14 -18.3(2) . . . . ? C8 C7 C15 C14 161.59(14) . . . . ? #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_dbm160_cu _database_code_depnum_ccdc_archive 'CCDC 739593' _audit_creation_date 2009-03-29T18:07:19-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; dibenzoylmethane ; _chemical_formula_sum 'C15 H12 O2' _chemical_formula_weight 224.25 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 8.6594(7) _cell_length_b 10.7139(11) _cell_length_c 24.359(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2260.0(4) _cell_formula_units_Z 8 _cell_measurement_temperature 160(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ; ? ; _exptl_crystal_description block _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_colour white #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.695 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _cell_measurement_reflns_used 5186 _cell_measurement_theta_min 13.64 _cell_measurement_theta_max 117.85 _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 1.54186 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; 'Rigaku R-AXIS RAPID IP Image Plate diffractometer' ; _diffrn_measurement_method \w _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_unetI/netI 0.0386 _diffrn_reflns_number 8915 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 6.82 _diffrn_reflns_theta_max 71.91 _diffrn_reflns_theta_full 71.91 _diffrn_measured_fraction_theta_full 0.977 _diffrn_measured_fraction_theta_max 0.977 _reflns_number_total 2166 _reflns_number_gt 1249 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Farrugia, 1997), Mercury (McRae, 2006)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0130P)^2^+1.9978P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.00098(9) _refine_ls_number_reflns 2166 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0868 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.1074 _refine_ls_wR_factor_gt 0.0677 _refine_ls_goodness_of_fit_ref 1.166 _refine_ls_restrained_S_all 1.166 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.270 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.065 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' 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 0.1848(3) 0.9458(2) 0.52144(9) 0.0296(5) Uani 1 1 d . . . C2 C 0.0798(3) 0.8813(2) 0.55456(10) 0.0341(6) Uani 1 1 d . . . C3 C 0.0374(3) 0.9284(3) 0.60534(10) 0.0378(6) Uani 1 1 d . . . C4 C 0.0971(3) 1.0413(3) 0.62360(10) 0.0385(6) Uani 1 1 d . . . C5 C 0.1993(3) 1.1071(3) 0.59056(10) 0.0372(6) Uani 1 1 d . . . C6 C 0.2435(3) 1.0591(2) 0.53991(9) 0.0342(6) Uani 1 1 d . . . C7 C 0.4696(3) 0.9623(2) 0.33912(9) 0.0306(6) Uani 1 1 d . . . C8 C 0.5236(3) 0.8898(3) 0.29542(10) 0.0357(6) Uani 1 1 d . . . C9 C 0.6248(3) 0.9385(3) 0.25700(10) 0.0395(6) Uani 1 1 d . . . C10 C 0.6732(3) 1.0618(3) 0.26118(10) 0.0418(7) Uani 1 1 d . . . C11 C 0.6202(3) 1.1351(3) 0.30432(10) 0.0403(7) Uani 1 1 d . . . C12 C 0.5203(3) 1.0865(2) 0.34345(10) 0.0341(6) Uani 1 1 d . . . C13 C 0.2269(3) 0.8945(2) 0.46669(9) 0.0322(6) Uani 1 1 d . . . C14 C 0.3336(3) 0.9546(2) 0.43105(9) 0.0317(6) Uani 1 1 d . . . C15 C 0.3622(3) 0.9066(2) 0.37945(9) 0.0315(6) Uani 1 1 d . . . O16 O 0.1616(2) 0.79202(16) 0.45213(7) 0.0404(5) Uani 1 1 d . . . O17 O 0.2923(2) 0.80368(16) 0.36282(7) 0.0393(5) Uani 1 1 d . . . H18 H 0.034(3) 0.803(2) 0.5401(8) 0.030(6) Uiso 1 1 d . . . H19 H -0.041(3) 0.882(2) 0.6290(9) 0.035(7) Uiso 1 1 d . . . H20 H 0.067(3) 1.075(2) 0.6614(10) 0.046(8) Uiso 1 1 d . . . H21 H 0.244(3) 1.187(2) 0.6037(9) 0.033(7) Uiso 1 1 d . . . H22 H 0.315(3) 1.111(2) 0.5167(9) 0.033(7) Uiso 1 1 d . . . H23 H 0.489(3) 0.804(2) 0.2924(8) 0.028(6) Uiso 1 1 d . . . H24 H 0.663(3) 0.884(2) 0.2259(10) 0.054(8) Uiso 1 1 d . . . H25 H 0.744(3) 1.101(2) 0.2324(10) 0.051(8) Uiso 1 1 d . . . H26 H 0.652(3) 1.222(2) 0.3090(10) 0.044(8) Uiso 1 1 d . . . H27 H 0.485(3) 1.139(2) 0.3746(10) 0.042(7) Uiso 1 1 d . . . H28 H 0.388(3) 1.032(2) 0.4433(9) 0.031(6) Uiso 1 1 d . . . H29 H 0.217(4) 0.779(4) 0.4023(15) 0.125(14) 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 C1 0.0278(12) 0.0295(13) 0.0316(12) 0.0044(10) -0.0025(10) 0.0006(11) C2 0.0332(14) 0.0289(14) 0.0402(14) 0.0041(11) -0.0007(11) -0.0023(12) C3 0.0325(14) 0.0435(17) 0.0374(14) 0.0101(12) 0.0053(11) 0.0006(13) C4 0.0425(16) 0.0404(16) 0.0327(14) 0.0044(12) 0.0046(12) 0.0019(13) C5 0.0383(15) 0.0376(16) 0.0358(14) -0.0007(11) -0.0008(12) -0.0046(13) C6 0.0352(14) 0.0382(15) 0.0290(12) 0.0051(11) -0.0002(11) -0.0030(12) C7 0.0301(13) 0.0347(14) 0.0270(12) -0.0004(10) -0.0028(10) 0.0029(11) C8 0.0392(15) 0.0364(15) 0.0314(13) -0.0051(11) -0.0055(11) 0.0025(13) C9 0.0416(15) 0.0461(17) 0.0307(13) -0.0066(12) 0.0015(12) 0.0038(13) C10 0.0420(16) 0.0511(18) 0.0324(14) 0.0029(12) 0.0038(12) 0.0021(14) C11 0.0446(17) 0.0407(17) 0.0354(14) -0.0020(12) 0.0061(12) 0.0008(14) C12 0.0379(15) 0.0352(14) 0.0292(13) -0.0017(11) 0.0012(11) 0.0048(12) C13 0.0310(13) 0.0314(14) 0.0341(13) 0.0028(10) -0.0089(11) 0.0024(11) C14 0.0351(14) 0.0285(13) 0.0314(12) 0.0004(10) 0.0002(10) -0.0016(12) C15 0.0320(14) 0.0289(14) 0.0336(13) -0.0003(10) -0.0054(10) 0.0025(11) O16 0.0493(12) 0.0342(10) 0.0377(10) 0.0023(8) -0.0028(9) -0.0073(9) O17 0.0485(12) 0.0327(10) 0.0369(9) -0.0036(8) -0.0030(8) -0.0029(9) _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 C6 1.391(3) . ? C1 C2 1.399(3) . ? C1 C13 1.488(3) . ? C2 C3 1.385(3) . ? C2 H18 0.99(2) . ? C3 C4 1.389(4) . ? C3 H19 1.02(2) . ? C4 C5 1.389(3) . ? C4 H20 1.02(2) . ? C5 C6 1.390(3) . ? C5 H21 0.99(2) . ? C6 H22 1.01(2) . ? C7 C12 1.405(3) . ? C7 C8 1.398(3) . ? C7 C15 1.479(3) . ? C8 C9 1.385(3) . ? C8 H23 0.97(2) . ? C9 C10 1.390(4) . ? C9 H24 1.01(2) . ? C10 C11 1.390(4) . ? C10 H25 1.02(3) . ? C11 C12 1.389(3) . ? C11 H26 0.98(2) . ? C12 H27 1.00(2) . ? C13 O16 1.285(3) . ? C13 C14 1.422(3) . ? C14 C15 1.380(3) . ? C14 H28 1.00(2) . ? C15 O17 1.322(3) . ? O16 H29 1.31(4) . ? O17 H29 1.19(4) . ? 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 C6 C1 C2 118.8(2) . . ? C6 C1 C13 121.5(2) . . ? C2 C1 C13 119.6(2) . . ? C3 C2 C1 120.5(2) . . ? C3 C2 H18 121.2(13) . . ? C1 C2 H18 118.2(13) . . ? C2 C3 C4 120.3(2) . . ? C2 C3 H19 120.3(13) . . ? C4 C3 H19 119.4(13) . . ? C5 C4 C3 119.6(2) . . ? C5 C4 H20 120.5(15) . . ? C3 C4 H20 119.9(14) . . ? C6 C5 C4 120.2(3) . . ? C6 C5 H21 119.9(13) . . ? C4 C5 H21 119.9(13) . . ? C5 C6 C1 120.6(2) . . ? C5 C6 H22 117.5(13) . . ? C1 C6 H22 121.8(13) . . ? C12 C7 C8 118.6(2) . . ? C12 C7 C15 121.9(2) . . ? C8 C7 C15 119.5(2) . . ? C9 C8 C7 121.1(3) . . ? C9 C8 H23 119.9(13) . . ? C7 C8 H23 118.9(13) . . ? C8 C9 C10 120.0(2) . . ? C8 C9 H24 119.8(15) . . ? C10 C9 H24 120.2(15) . . ? C9 C10 C11 119.6(3) . . ? C9 C10 H25 121.3(14) . . ? C11 C10 H25 119.1(14) . . ? C12 C11 C10 120.8(3) . . ? C12 C11 H26 116.9(14) . . ? C10 C11 H26 122.2(15) . . ? C11 C12 C7 119.9(2) . . ? C11 C12 H27 120.0(15) . . ? C7 C12 H27 120.1(14) . . ? O16 C13 C14 120.3(2) . . ? O16 C13 C1 117.1(2) . . ? C14 C13 C1 122.6(2) . . ? C15 C14 C13 120.2(2) . . ? C15 C14 H28 119.8(13) . . ? C13 C14 H28 120.0(13) . . ? O17 C15 C14 120.5(2) . . ? O17 C15 C7 114.9(2) . . ? C14 C15 C7 124.6(2) . . ? C13 O16 H29 100.5(17) . . ? C15 O17 H29 100.7(18) . . ? 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 C6 C1 C2 C3 -1.2(4) . . . . ? C13 C1 C2 C3 -179.1(2) . . . . ? C1 C2 C3 C4 1.0(4) . . . . ? C2 C3 C4 C5 0.2(4) . . . . ? C3 C4 C5 C6 -1.0(4) . . . . ? C4 C5 C6 C1 0.7(4) . . . . ? C2 C1 C6 C5 0.4(4) . . . . ? C13 C1 C6 C5 178.2(2) . . . . ? C12 C7 C8 C9 0.0(4) . . . . ? C15 C7 C8 C9 -179.7(2) . . . . ? C7 C8 C9 C10 -0.7(4) . . . . ? C8 C9 C10 C11 0.5(4) . . . . ? C9 C10 C11 C12 0.3(4) . . . . ? C10 C11 C12 C7 -1.0(4) . . . . ? C8 C7 C12 C11 0.8(4) . . . . ? C15 C7 C12 C11 -179.4(2) . . . . ? C6 C1 C13 O16 -176.9(2) . . . . ? C2 C1 C13 O16 0.8(3) . . . . ? C6 C1 C13 C14 2.6(4) . . . . ? C2 C1 C13 C14 -179.6(2) . . . . ? O16 C13 C14 C15 3.1(4) . . . . ? C1 C13 C14 C15 -176.4(2) . . . . ? C13 C14 C15 O17 -0.8(4) . . . . ? C13 C14 C15 C7 179.5(2) . . . . ? C12 C7 C15 O17 162.4(2) . . . . ? C8 C7 C15 O17 -17.9(3) . . . . ? C12 C7 C15 C14 -17.9(4) . . . . ? C8 C7 C15 C14 161.8(2) . . . . ? #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_dbm200_cu _database_code_depnum_ccdc_archive 'CCDC 739594' _audit_creation_date 2009-03-29T18:07:44-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; dibenzoylmethane ; _chemical_formula_sum 'C15 H12 O2' _chemical_formula_weight 224.25 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 8.6886(5) _cell_length_b 10.7434(7) _cell_length_c 24.4019(16) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2277.8(2) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ; ? ; _exptl_crystal_description block _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_colour white #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.69 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _cell_measurement_reflns_used 6741 _cell_measurement_theta_min 13.11 _cell_measurement_theta_max 117.85 _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 1.54186 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; 'Rigaku R-AXIS RAPID IP Image Plate diffractometer' ; _diffrn_measurement_method \w _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_unetI/netI 0.0193 _diffrn_reflns_number 9700 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 6.8 _diffrn_reflns_theta_max 72.11 _diffrn_reflns_theta_full 72.11 _diffrn_measured_fraction_theta_full 0.945 _diffrn_measured_fraction_theta_max 0.944 _reflns_number_total 2113 _reflns_number_gt 1719 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Farrugia, 1997), Mercury (McRae, 2006)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0385P)^2^+0.5433P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.00147(19) _refine_ls_number_reflns 2113 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0932 _refine_ls_wR_factor_gt 0.0855 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.147 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.031 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' 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 0.18590(14) 0.94540(12) 0.52082(5) 0.0347(3) Uani 1 1 d . . . C2 C 0.08146(16) 0.88041(14) 0.55387(6) 0.0409(3) Uani 1 1 d . . . C3 C 0.03869(17) 0.92766(15) 0.60459(6) 0.0451(4) Uani 1 1 d . . . C4 C 0.09779(17) 1.03980(15) 0.62269(6) 0.0444(4) Uani 1 1 d . . . C5 C 0.19968(17) 1.10564(15) 0.59005(6) 0.0428(4) Uani 1 1 d . . . C6 C 0.24359(16) 1.05863(14) 0.53951(5) 0.0391(3) Uani 1 1 d . . . C7 C 0.47008(15) 0.96359(13) 0.33892(5) 0.0356(3) Uani 1 1 d . . . C8 C 0.52407(17) 0.89111(15) 0.29516(6) 0.0422(4) Uani 1 1 d . . . C9 C 0.62490(18) 0.94101(16) 0.25708(6) 0.0480(4) Uani 1 1 d . . . C10 C 0.67155(18) 1.06376(16) 0.26144(6) 0.0496(4) Uani 1 1 d . . . C11 C 0.61872(18) 1.13653(16) 0.30450(6) 0.0465(4) Uani 1 1 d . . . C12 C 0.51942(16) 1.08657(13) 0.34334(6) 0.0400(3) Uani 1 1 d . . . C13 C 0.22765(15) 0.89433(13) 0.46620(5) 0.0368(3) Uani 1 1 d . . . C14 C 0.33342(15) 0.95463(13) 0.43062(5) 0.0369(3) Uani 1 1 d . . . C15 C 0.36259(15) 0.90651(13) 0.37890(5) 0.0359(3) Uani 1 1 d . . . O16 O 0.16368(12) 0.79204(9) 0.45151(4) 0.0457(3) Uani 1 1 d . . . O17 O 0.29408(12) 0.80427(9) 0.36238(4) 0.0468(3) Uani 1 1 d . . . H18 H 0.0382(17) 0.8025(14) 0.5400(6) 0.047(4) Uiso 1 1 d . . . H19 H -0.0352(19) 0.8804(15) 0.6276(7) 0.056(5) Uiso 1 1 d . . . H20 H 0.0665(18) 1.0713(14) 0.6595(6) 0.055(4) Uiso 1 1 d . . . H21 H 0.2405(18) 1.1884(15) 0.6027(6) 0.051(4) Uiso 1 1 d . . . H22 H 0.3152(16) 1.1071(13) 0.5171(6) 0.040(4) Uiso 1 1 d . . . H23 H 0.4911(17) 0.8039(15) 0.2926(6) 0.049(4) Uiso 1 1 d . . . H24 H 0.6639(18) 0.8865(15) 0.2272(7) 0.060(5) Uiso 1 1 d . . . H25 H 0.744(2) 1.1003(15) 0.2344(7) 0.060(5) Uiso 1 1 d . . . H26 H 0.6506(18) 1.2256(16) 0.3071(6) 0.054(5) Uiso 1 1 d . . . H27 H 0.4849(17) 1.1410(13) 0.3740(6) 0.044(4) Uiso 1 1 d . . . H28 H 0.3846(17) 1.0308(14) 0.4429(6) 0.041(4) Uiso 1 1 d . . . H29 H 0.222(3) 0.777(2) 0.4025(9) 0.109(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 C1 0.0325(7) 0.0364(8) 0.0352(7) 0.0071(5) -0.0030(5) 0.0026(6) C2 0.0386(8) 0.0367(9) 0.0474(8) 0.0081(6) -0.0007(6) -0.0009(6) C3 0.0402(8) 0.0485(10) 0.0465(8) 0.0133(7) 0.0083(6) 0.0014(7) C4 0.0449(8) 0.0506(10) 0.0378(8) 0.0046(6) 0.0054(6) 0.0030(7) C5 0.0452(8) 0.0445(10) 0.0386(8) 0.0014(6) 0.0017(6) -0.0038(7) C6 0.0378(7) 0.0435(9) 0.0359(7) 0.0065(6) 0.0014(6) -0.0034(6) C7 0.0351(7) 0.0388(8) 0.0331(7) -0.0007(5) -0.0036(5) 0.0070(6) C8 0.0455(8) 0.0430(9) 0.0381(8) -0.0066(6) -0.0058(6) 0.0056(7) C9 0.0480(9) 0.0609(11) 0.0352(8) -0.0094(7) 0.0005(6) 0.0094(7) C10 0.0476(9) 0.0638(11) 0.0373(8) 0.0022(7) 0.0054(6) 0.0020(8) C11 0.0520(9) 0.0443(10) 0.0434(8) 0.0020(6) 0.0050(6) 0.0021(7) C12 0.0437(8) 0.0405(9) 0.0356(7) -0.0023(6) 0.0027(6) 0.0062(6) C13 0.0351(7) 0.0344(8) 0.0408(7) 0.0054(5) -0.0058(6) 0.0032(6) C14 0.0375(7) 0.0358(8) 0.0374(7) -0.0010(5) -0.0012(5) -0.0006(6) C15 0.0360(7) 0.0327(8) 0.0391(7) 0.0001(5) -0.0078(5) 0.0051(6) O16 0.0539(6) 0.0381(6) 0.0449(6) 0.0028(4) -0.0039(5) -0.0083(5) O17 0.0573(7) 0.0397(6) 0.0434(6) -0.0048(4) -0.0030(5) -0.0044(5) _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 C6 1.3925(19) . ? C1 C2 1.4005(18) . ? C1 C13 1.4863(19) . ? C2 C3 1.388(2) . ? C2 H18 0.978(15) . ? C3 C4 1.382(2) . ? C3 H19 0.993(16) . ? C4 C5 1.385(2) . ? C4 H20 0.998(15) . ? C5 C6 1.3862(19) . ? C5 H21 1.005(16) . ? C6 H22 0.978(14) . ? C7 C12 1.393(2) . ? C7 C8 1.4023(18) . ? C7 C15 1.4833(19) . ? C8 C9 1.385(2) . ? C8 H23 0.982(16) . ? C9 C10 1.384(2) . ? C9 H24 0.994(16) . ? C10 C11 1.388(2) . ? C10 H25 0.993(17) . ? C11 C12 1.390(2) . ? C11 H26 0.999(16) . ? C12 H27 0.995(15) . ? C13 O16 1.2826(16) . ? C13 C14 1.4206(19) . ? C14 C15 1.3871(19) . ? C14 H28 0.978(15) . ? C15 O17 1.3127(16) . ? O16 H29 1.31(2) . ? O17 H29 1.20(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 C6 C1 C2 118.70(13) . . ? C6 C1 C13 121.89(12) . . ? C2 C1 C13 119.38(13) . . ? C3 C2 C1 120.30(15) . . ? C3 C2 H18 121.2(9) . . ? C1 C2 H18 118.5(9) . . ? C2 C3 C4 120.27(14) . . ? C2 C3 H19 119.3(9) . . ? C4 C3 H19 120.4(9) . . ? C5 C4 C3 119.93(14) . . ? C5 C4 H20 121.2(9) . . ? C3 C4 H20 118.8(9) . . ? C6 C5 C4 120.10(15) . . ? C6 C5 H21 119.8(9) . . ? C4 C5 H21 120.1(9) . . ? C5 C6 C1 120.70(13) . . ? C5 C6 H22 118.6(8) . . ? C1 C6 H22 120.7(8) . . ? C12 C7 C8 118.86(13) . . ? C12 C7 C15 122.33(12) . . ? C8 C7 C15 118.81(13) . . ? C9 C8 C7 120.49(15) . . ? C9 C8 H23 120.7(9) . . ? C7 C8 H23 118.8(9) . . ? C8 C9 C10 120.18(14) . . ? C8 C9 H24 118.7(9) . . ? C10 C9 H24 121.2(9) . . ? C9 C10 C11 119.88(15) . . ? C9 C10 H25 120.7(9) . . ? C11 C10 H25 119.4(9) . . ? C12 C11 C10 120.28(16) . . ? C12 C11 H26 120.0(9) . . ? C10 C11 H26 119.7(9) . . ? C11 C12 C7 120.30(13) . . ? C11 C12 H27 118.2(9) . . ? C7 C12 H27 121.5(9) . . ? O16 C13 C14 120.02(12) . . ? O16 C13 C1 117.46(12) . . ? C14 C13 C1 122.53(13) . . ? C15 C14 C13 120.29(13) . . ? C15 C14 H28 120.6(8) . . ? C13 C14 H28 119.2(8) . . ? O17 C15 C14 120.55(13) . . ? O17 C15 C7 115.43(11) . . ? C14 C15 C7 124.01(13) . . ? C13 O16 H29 101.1(10) . . ? C15 O17 H29 100.9(11) . . ? 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 C6 C1 C2 C3 -1.0(2) . . . . ? C13 C1 C2 C3 -178.79(12) . . . . ? C1 C2 C3 C4 0.6(2) . . . . ? C2 C3 C4 C5 0.2(2) . . . . ? C3 C4 C5 C6 -0.6(2) . . . . ? C4 C5 C6 C1 0.2(2) . . . . ? C2 C1 C6 C5 0.6(2) . . . . ? C13 C1 C6 C5 178.34(12) . . . . ? C12 C7 C8 C9 0.1(2) . . . . ? C15 C7 C8 C9 -179.81(12) . . . . ? C7 C8 C9 C10 -1.0(2) . . . . ? C8 C9 C10 C11 0.9(2) . . . . ? C9 C10 C11 C12 0.2(2) . . . . ? C10 C11 C12 C7 -1.0(2) . . . . ? C8 C7 C12 C11 0.9(2) . . . . ? C15 C7 C12 C11 -179.19(13) . . . . ? C6 C1 C13 O16 -177.05(12) . . . . ? C2 C1 C13 O16 0.69(18) . . . . ? C6 C1 C13 C14 2.7(2) . . . . ? C2 C1 C13 C14 -179.58(12) . . . . ? O16 C13 C14 C15 3.0(2) . . . . ? C1 C13 C14 C15 -176.69(12) . . . . ? C13 C14 C15 O17 -0.6(2) . . . . ? C13 C14 C15 C7 179.53(12) . . . . ? C12 C7 C15 O17 162.34(12) . . . . ? C8 C7 C15 O17 -17.74(17) . . . . ? C12 C7 C15 C14 -17.8(2) . . . . ? C8 C7 C15 C14 162.12(13) . . . . ? #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_dbm240_cu _database_code_depnum_ccdc_archive 'CCDC 739595' _audit_creation_date 2009-03-29T18:08:06-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; dibenzoylmethane ; _chemical_formula_sum 'C15 H12 O2' _chemical_formula_weight 224.25 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 8.7228(10) _cell_length_b 10.7969(12) _cell_length_c 24.423(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2300.2(5) _cell_formula_units_Z 8 _cell_measurement_temperature 240(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ; ? ; _exptl_crystal_description block _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_colour white #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.683 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _cell_measurement_reflns_used 2800 _cell_measurement_theta_min 13.05 _cell_measurement_theta_max 118.18 _diffrn_ambient_temperature 240(2) _diffrn_radiation_wavelength 1.54186 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; 'Rigaku R-AXIS RAPID IP Image Plate diffractometer' ; _diffrn_measurement_method \w _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_unetI/netI 0.0258 _diffrn_reflns_number 9247 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 6.77 _diffrn_reflns_theta_max 71.86 _diffrn_reflns_theta_full 71.86 _diffrn_measured_fraction_theta_full 0.956 _diffrn_measured_fraction_theta_max 0.956 _reflns_number_total 2154 _reflns_number_gt 1477 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Farrugia, 1997), Mercury (McRae, 2006)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0217P)^2^+0.7097P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.00287(17) _refine_ls_number_reflns 2154 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0619 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.0938 _refine_ls_wR_factor_gt 0.0746 _refine_ls_goodness_of_fit_ref 1.130 _refine_ls_restrained_S_all 1.130 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.177 _refine_diff_density_min -0.152 _refine_diff_density_rms 0.035 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' 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 0.18672(19) 0.94441(16) 0.52013(7) 0.0441(4) Uani 1 1 d . . . C2 C 0.0832(2) 0.87977(19) 0.55296(8) 0.0532(5) Uani 1 1 d . . . C3 C 0.0407(2) 0.9263(2) 0.60351(9) 0.0596(6) Uani 1 1 d . . . C4 C 0.0984(2) 1.0379(2) 0.62177(9) 0.0580(5) Uani 1 1 d . . . C5 C 0.1995(2) 1.1035(2) 0.58923(8) 0.0569(5) Uani 1 1 d . . . C6 C 0.2438(2) 1.05717(18) 0.53876(7) 0.0503(5) Uani 1 1 d . . . C7 C 0.4700(2) 0.96432(17) 0.33865(7) 0.0460(5) Uani 1 1 d . . . C8 C 0.5242(2) 0.8934(2) 0.29503(8) 0.0552(5) Uani 1 1 d . . . C9 C 0.6242(3) 0.9438(2) 0.25714(8) 0.0629(6) Uani 1 1 d . . . C10 C 0.6704(3) 1.0659(2) 0.26160(8) 0.0646(6) Uani 1 1 d . . . C11 C 0.6166(3) 1.1371(2) 0.30463(8) 0.0602(6) Uani 1 1 d . . . C12 C 0.5182(2) 1.08695(18) 0.34322(8) 0.0530(5) Uani 1 1 d . . . C13 C 0.2288(2) 0.89437(17) 0.46557(7) 0.0478(5) Uani 1 1 d . . . C14 C 0.3330(2) 0.95446(18) 0.43008(7) 0.0472(5) Uani 1 1 d . . . C15 C 0.3634(2) 0.90713(17) 0.37839(7) 0.0470(5) Uani 1 1 d . . . O16 O 0.16592(15) 0.79193(11) 0.45096(5) 0.0601(4) Uani 1 1 d . . . O17 O 0.29617(16) 0.80488(12) 0.36189(5) 0.0612(4) Uani 1 1 d . . . H18 H 0.041(2) 0.8003(17) 0.5395(7) 0.062(6) Uiso 1 1 d . . . H19 H -0.031(2) 0.8788(18) 0.6275(8) 0.075(6) Uiso 1 1 d . . . H20 H 0.066(2) 1.0706(18) 0.6586(8) 0.077(6) Uiso 1 1 d . . . H21 H 0.240(2) 1.1857(19) 0.6018(7) 0.073(6) Uiso 1 1 d . . . H22 H 0.315(2) 1.1083(16) 0.5153(7) 0.059(5) Uiso 1 1 d . . . H23 H 0.492(2) 0.8056(18) 0.2922(7) 0.063(6) Uiso 1 1 d . . . H24 H 0.662(2) 0.8915(19) 0.2266(8) 0.085(7) Uiso 1 1 d . . . H25 H 0.742(3) 1.1048(19) 0.2344(8) 0.083(7) Uiso 1 1 d . . . H26 H 0.648(2) 1.2248(18) 0.3084(7) 0.064(6) Uiso 1 1 d . . . H27 H 0.483(2) 1.1396(16) 0.3742(7) 0.056(5) Uiso 1 1 d . . . H28 H 0.3849(19) 1.0313(16) 0.4420(7) 0.053(5) Uiso 1 1 d . . . H29 H 0.220(3) 0.776(3) 0.4025(12) 0.146(11) 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 C1 0.0430(10) 0.0440(11) 0.0453(10) 0.0088(8) -0.0026(8) 0.0033(8) C2 0.0504(12) 0.0474(12) 0.0617(13) 0.0107(10) 0.0006(10) -0.0025(9) C3 0.0540(13) 0.0634(14) 0.0613(13) 0.0158(11) 0.0105(10) 0.0007(10) C4 0.0575(13) 0.0654(14) 0.0510(12) 0.0059(10) 0.0071(10) 0.0029(10) C5 0.0611(13) 0.0594(14) 0.0503(12) 0.0024(10) 0.0041(10) -0.0076(10) C6 0.0498(11) 0.0547(12) 0.0465(11) 0.0072(9) 0.0016(9) -0.0041(9) C7 0.0463(11) 0.0494(11) 0.0423(10) -0.0011(8) -0.0040(8) 0.0076(8) C8 0.0600(13) 0.0570(14) 0.0486(11) -0.0090(9) -0.0040(9) 0.0071(10) C9 0.0634(14) 0.0797(17) 0.0457(12) -0.0122(11) 0.0002(10) 0.0103(12) C10 0.0638(14) 0.0810(17) 0.0489(13) 0.0007(11) 0.0075(10) 0.0038(12) C11 0.0685(14) 0.0572(14) 0.0548(13) 0.0006(10) 0.0081(10) 0.0014(11) C12 0.0600(13) 0.0529(12) 0.0461(12) -0.0014(9) 0.0053(9) 0.0074(10) C13 0.0474(11) 0.0431(11) 0.0528(11) 0.0051(8) -0.0082(9) 0.0032(8) C14 0.0486(11) 0.0457(11) 0.0471(11) -0.0002(8) -0.0001(8) -0.0030(9) C15 0.0479(11) 0.0439(11) 0.0493(11) -0.0015(8) -0.0081(8) 0.0052(8) O16 0.0718(10) 0.0484(8) 0.0600(9) 0.0020(6) -0.0047(7) -0.0101(7) O17 0.0748(10) 0.0505(8) 0.0584(8) -0.0056(6) -0.0049(7) -0.0055(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 C6 1.392(2) . ? C1 C2 1.395(2) . ? C1 C13 1.484(2) . ? C2 C3 1.383(3) . ? C2 H18 0.990(18) . ? C3 C4 1.380(3) . ? C3 H19 1.00(2) . ? C4 C5 1.383(3) . ? C4 H20 1.01(2) . ? C5 C6 1.385(3) . ? C5 H21 1.00(2) . ? C6 H22 1.007(18) . ? C7 C8 1.395(2) . ? C7 C12 1.394(3) . ? C7 C15 1.479(2) . ? C8 C9 1.383(3) . ? C8 H23 0.989(18) . ? C9 C10 1.383(3) . ? C9 H24 0.99(2) . ? C10 C11 1.385(3) . ? C10 H25 1.00(2) . ? C11 C12 1.386(3) . ? C11 H26 0.989(19) . ? C12 H27 0.993(17) . ? C13 O16 1.285(2) . ? C13 C14 1.414(2) . ? C14 C15 1.387(2) . ? C14 H28 0.988(17) . ? C15 O17 1.314(2) . ? O16 H29 1.29(3) . ? O17 H29 1.23(3) . ? 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 C6 C1 C2 118.77(17) . . ? C6 C1 C13 121.57(16) . . ? C2 C1 C13 119.62(17) . . ? C3 C2 C1 120.3(2) . . ? C3 C2 H18 120.9(11) . . ? C1 C2 H18 118.8(10) . . ? C2 C3 C4 120.5(2) . . ? C2 C3 H19 120.3(11) . . ? C4 C3 H19 119.2(11) . . ? C5 C4 C3 119.7(2) . . ? C5 C4 H20 120.9(12) . . ? C3 C4 H20 119.4(12) . . ? C6 C5 C4 120.3(2) . . ? C6 C5 H21 119.5(11) . . ? C4 C5 H21 120.3(11) . . ? C5 C6 C1 120.49(18) . . ? C5 C6 H22 118.6(10) . . ? C1 C6 H22 120.8(10) . . ? C8 C7 C12 118.74(18) . . ? C8 C7 C15 119.01(18) . . ? C12 C7 C15 122.24(16) . . ? C9 C8 C7 120.6(2) . . ? C9 C8 H23 120.5(11) . . ? C7 C8 H23 118.9(11) . . ? C8 C9 C10 120.4(2) . . ? C8 C9 H24 119.4(12) . . ? C10 C9 H24 120.2(12) . . ? C11 C10 C9 119.4(2) . . ? C11 C10 H25 118.7(12) . . ? C9 C10 H25 121.9(12) . . ? C12 C11 C10 120.6(2) . . ? C12 C11 H26 118.7(11) . . ? C10 C11 H26 120.7(11) . . ? C11 C12 C7 120.26(19) . . ? C11 C12 H27 118.9(10) . . ? C7 C12 H27 120.8(10) . . ? O16 C13 C14 119.94(17) . . ? O16 C13 C1 117.19(16) . . ? C14 C13 C1 122.86(17) . . ? C15 C14 C13 120.77(18) . . ? C15 C14 H28 119.3(10) . . ? C13 C14 H28 119.9(10) . . ? O17 C15 C14 120.24(17) . . ? O17 C15 C7 115.47(16) . . ? C14 C15 C7 124.29(17) . . ? C13 O16 H29 102.2(13) . . ? C15 O17 H29 101.8(13) . . ? 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 C6 C1 C2 C3 -1.2(3) . . . . ? C13 C1 C2 C3 -178.88(17) . . . . ? C1 C2 C3 C4 0.9(3) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? C3 C4 C5 C6 -0.5(3) . . . . ? C4 C5 C6 C1 0.2(3) . . . . ? C2 C1 C6 C5 0.6(3) . . . . ? C13 C1 C6 C5 178.25(17) . . . . ? C12 C7 C8 C9 0.2(3) . . . . ? C15 C7 C8 C9 -179.89(17) . . . . ? C7 C8 C9 C10 -0.8(3) . . . . ? C8 C9 C10 C11 0.5(3) . . . . ? C9 C10 C11 C12 0.4(3) . . . . ? C10 C11 C12 C7 -1.1(3) . . . . ? C8 C7 C12 C11 0.7(3) . . . . ? C15 C7 C12 C11 -179.17(17) . . . . ? C6 C1 C13 O16 -177.36(16) . . . . ? C2 C1 C13 O16 0.2(2) . . . . ? C6 C1 C13 C14 2.5(3) . . . . ? C2 C1 C13 C14 -179.90(16) . . . . ? O16 C13 C14 C15 2.9(3) . . . . ? C1 C13 C14 C15 -176.96(16) . . . . ? C13 C14 C15 O17 -0.5(3) . . . . ? C13 C14 C15 C7 179.69(16) . . . . ? C8 C7 C15 O17 -17.4(2) . . . . ? C12 C7 C15 O17 162.52(17) . . . . ? C8 C7 C15 C14 162.42(17) . . . . ? C12 C7 C15 C14 -17.7(3) . . . . ? #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_dbm280_cu _database_code_depnum_ccdc_archive 'CCDC 739596' _audit_creation_date 2009-03-29T18:08:28-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; dibenzoylmethane ; _chemical_formula_sum 'C15 H12 O2' _chemical_formula_weight 224.25 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 8.7652(8) _cell_length_b 10.8627(9) _cell_length_c 24.513(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2334.0(4) _cell_formula_units_Z 8 _cell_measurement_temperature 280(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ; ? ; _exptl_crystal_description block _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_colour white #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.673 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _cell_measurement_reflns_used 6742 _cell_measurement_theta_min 13.47 _cell_measurement_theta_max 118.19 _diffrn_ambient_temperature 280(2) _diffrn_radiation_wavelength 1.54186 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; 'Rigaku R-AXIS RAPID IP Image Plate diffractometer' ; _diffrn_measurement_method \w _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_unetI/netI 0.0172 _diffrn_reflns_number 18401 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 6.74 _diffrn_reflns_theta_max 71.74 _diffrn_reflns_theta_full 71.74 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _reflns_number_total 2264 _reflns_number_gt 1697 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Farrugia, 1997), Mercury (McRae, 2006)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0330P)^2^+0.6791P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0028(2) _refine_ls_number_reflns 2264 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0553 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1108 _refine_ls_wR_factor_gt 0.0915 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.109 _refine_diff_density_min -0.141 _refine_diff_density_rms 0.029 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' 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 0.18772(19) 0.94400(16) 0.51921(7) 0.0544(4) Uani 1 1 d . . . C2 C 0.0850(2) 0.87880(19) 0.55219(8) 0.0656(5) Uani 1 1 d . . . C3 C 0.0427(2) 0.9251(2) 0.60261(8) 0.0732(6) Uani 1 1 d . . . C4 C 0.0993(2) 1.0360(2) 0.62081(8) 0.0707(5) Uani 1 1 d . . . C5 C 0.1993(2) 1.1015(2) 0.58841(8) 0.0692(6) Uani 1 1 d . . . C6 C 0.2436(2) 1.05611(18) 0.53809(7) 0.0613(5) Uani 1 1 d . . . C7 C 0.4701(2) 0.96587(17) 0.33837(6) 0.0561(4) Uani 1 1 d . . . C8 C 0.5249(2) 0.8957(2) 0.29470(7) 0.0677(5) Uani 1 1 d . . . C9 C 0.6240(3) 0.9469(2) 0.25718(8) 0.0775(6) Uani 1 1 d . . . C10 C 0.6688(3) 1.0683(2) 0.26182(8) 0.0784(6) Uani 1 1 d . . . C11 C 0.6149(3) 1.1387(2) 0.30479(8) 0.0740(6) Uani 1 1 d . . . C12 C 0.5172(2) 1.08765(18) 0.34315(7) 0.0638(5) Uani 1 1 d . . . C13 C 0.2301(2) 0.89439(17) 0.46487(7) 0.0575(5) Uani 1 1 d . . . C14 C 0.3332(2) 0.95445(18) 0.42936(7) 0.0581(5) Uani 1 1 d . . . C15 C 0.3640(2) 0.90783(16) 0.37792(7) 0.0567(4) Uani 1 1 d . . . O16 O 0.16804(16) 0.79197(12) 0.45026(6) 0.0735(4) Uani 1 1 d . . . O17 O 0.29849(17) 0.80588(12) 0.36131(5) 0.0744(4) Uani 1 1 d . . . H18 H 0.043(2) 0.8020(19) 0.5375(8) 0.082(6) Uiso 1 1 d . . . H19 H -0.028(2) 0.8804(19) 0.6257(9) 0.089(7) Uiso 1 1 d . . . H20 H 0.069(2) 1.0692(18) 0.6585(8) 0.085(6) Uiso 1 1 d . . . H21 H 0.240(2) 1.183(2) 0.6011(8) 0.085(6) Uiso 1 1 d . . . H22 H 0.315(2) 1.1067(17) 0.5145(7) 0.074(6) Uiso 1 1 d . . . H23 H 0.492(2) 0.8086(19) 0.2914(8) 0.078(6) Uiso 1 1 d . . . H24 H 0.661(2) 0.8956(19) 0.2270(9) 0.096(7) Uiso 1 1 d . . . H25 H 0.739(3) 1.1077(19) 0.2352(9) 0.094(7) Uiso 1 1 d . . . H26 H 0.646(2) 1.2256(19) 0.3086(8) 0.080(6) Uiso 1 1 d . . . H27 H 0.482(2) 1.1391(17) 0.3741(8) 0.071(5) Uiso 1 1 d . . . H28 H 0.383(2) 1.0297(17) 0.4417(7) 0.065(5) Uiso 1 1 d . . . H29 H 0.223(3) 0.779(3) 0.4032(11) 0.136(9) 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 C1 0.0509(9) 0.0558(10) 0.0565(9) 0.0107(8) -0.0041(7) 0.0033(8) C2 0.0606(11) 0.0607(12) 0.0756(12) 0.0132(10) 0.0019(10) -0.0035(10) C3 0.0663(13) 0.0807(15) 0.0726(13) 0.0195(11) 0.0147(10) 0.0017(11) C4 0.0707(13) 0.0790(14) 0.0622(11) 0.0064(10) 0.0082(10) 0.0022(11) C5 0.0748(13) 0.0737(14) 0.0590(11) 0.0035(10) 0.0047(9) -0.0088(11) C6 0.0623(11) 0.0658(12) 0.0556(10) 0.0078(9) 0.0026(9) -0.0068(9) C7 0.0571(10) 0.0609(11) 0.0503(9) -0.0019(8) -0.0046(7) 0.0098(9) C8 0.0706(12) 0.0749(14) 0.0577(11) -0.0125(9) -0.0057(9) 0.0085(11) C9 0.0769(14) 0.1006(18) 0.0551(11) -0.0156(11) 0.0016(10) 0.0130(13) C10 0.0775(14) 0.0988(18) 0.0591(12) 0.0023(11) 0.0098(10) 0.0035(13) C11 0.0842(14) 0.0723(14) 0.0655(12) 0.0023(10) 0.0107(10) 0.0007(12) C12 0.0718(12) 0.0631(12) 0.0566(10) -0.0021(9) 0.0055(9) 0.0100(10) C13 0.0573(10) 0.0526(10) 0.0627(10) 0.0051(8) -0.0092(8) 0.0031(8) C14 0.0594(11) 0.0579(11) 0.0569(10) -0.0008(8) -0.0008(8) -0.0032(9) C15 0.0587(10) 0.0527(10) 0.0587(10) -0.0019(8) -0.0102(8) 0.0074(8) O16 0.0867(10) 0.0606(8) 0.0731(9) 0.0036(7) -0.0040(7) -0.0113(7) O17 0.0928(10) 0.0603(8) 0.0702(8) -0.0080(6) -0.0049(7) -0.0056(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 C6 1.392(2) . ? C1 C2 1.402(2) . ? C1 C13 1.484(2) . ? C2 C3 1.385(3) . ? C2 H18 0.98(2) . ? C3 C4 1.378(3) . ? C3 H19 0.97(2) . ? C4 C5 1.380(3) . ? C4 H20 1.03(2) . ? C5 C6 1.384(3) . ? C5 H21 1.01(2) . ? C6 H22 1.013(19) . ? C7 C8 1.399(2) . ? C7 C12 1.391(3) . ? C7 C15 1.484(2) . ? C8 C9 1.382(3) . ? C8 H23 0.99(2) . ? C9 C10 1.380(3) . ? C9 H24 0.98(2) . ? C10 C11 1.384(3) . ? C10 H25 1.00(2) . ? C11 C12 1.387(3) . ? C11 H26 0.99(2) . ? C12 H27 0.993(19) . ? C13 O16 1.289(2) . ? C13 C14 1.414(2) . ? C14 C15 1.385(2) . ? C14 H28 0.976(18) . ? C15 O17 1.312(2) . ? O16 H29 1.26(3) . ? O17 H29 1.25(3) . ? 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 C6 C1 C2 118.45(17) . . ? C6 C1 C13 121.86(16) . . ? C2 C1 C13 119.66(17) . . ? C3 C2 C1 120.2(2) . . ? C3 C2 H18 122.3(12) . . ? C1 C2 H18 117.4(12) . . ? C2 C3 C4 120.7(2) . . ? C2 C3 H19 120.7(13) . . ? C4 C3 H19 118.6(12) . . ? C5 C4 C3 119.6(2) . . ? C5 C4 H20 120.1(12) . . ? C3 C4 H20 120.3(12) . . ? C6 C5 C4 120.5(2) . . ? C6 C5 H21 119.4(12) . . ? C4 C5 H21 120.1(11) . . ? C5 C6 C1 120.62(18) . . ? C5 C6 H22 119.2(11) . . ? C1 C6 H22 120.1(10) . . ? C8 C7 C12 118.73(18) . . ? C8 C7 C15 118.92(18) . . ? C12 C7 C15 122.35(16) . . ? C9 C8 C7 120.4(2) . . ? C9 C8 H23 120.9(11) . . ? C7 C8 H23 118.8(12) . . ? C8 C9 C10 120.5(2) . . ? C8 C9 H24 118.9(13) . . ? C10 C9 H24 120.6(13) . . ? C11 C10 C9 119.6(2) . . ? C11 C10 H25 118.2(13) . . ? C9 C10 H25 122.2(12) . . ? C12 C11 C10 120.4(2) . . ? C12 C11 H26 119.3(12) . . ? C10 C11 H26 120.3(12) . . ? C11 C12 C7 120.40(18) . . ? C11 C12 H27 119.2(11) . . ? C7 C12 H27 120.4(11) . . ? O16 C13 C14 119.79(17) . . ? O16 C13 C1 117.19(16) . . ? C14 C13 C1 123.02(17) . . ? C15 C14 C13 121.09(18) . . ? C15 C14 H28 120.0(10) . . ? C13 C14 H28 118.9(10) . . ? O17 C15 C14 120.35(17) . . ? O17 C15 C7 115.48(15) . . ? C14 C15 C7 124.18(17) . . ? C13 O16 H29 100.7(13) . . ? C15 O17 H29 99.8(12) . . ? 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 C6 C1 C2 C3 -0.9(3) . . . . ? C13 C1 C2 C3 -179.00(17) . . . . ? C1 C2 C3 C4 0.7(3) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? C3 C4 C5 C6 -0.4(3) . . . . ? C4 C5 C6 C1 0.2(3) . . . . ? C2 C1 C6 C5 0.4(3) . . . . ? C13 C1 C6 C5 178.46(17) . . . . ? C12 C7 C8 C9 0.0(3) . . . . ? C15 C7 C8 C9 -179.91(17) . . . . ? C7 C8 C9 C10 -0.9(3) . . . . ? C8 C9 C10 C11 0.7(3) . . . . ? C9 C10 C11 C12 0.3(3) . . . . ? C10 C11 C12 C7 -1.1(3) . . . . ? C8 C7 C12 C11 0.9(3) . . . . ? C15 C7 C12 C11 -179.10(17) . . . . ? C6 C1 C13 O16 -177.56(16) . . . . ? C2 C1 C13 O16 0.5(2) . . . . ? C6 C1 C13 C14 2.2(3) . . . . ? C2 C1 C13 C14 -179.80(16) . . . . ? O16 C13 C14 C15 2.8(3) . . . . ? C1 C13 C14 C15 -176.93(16) . . . . ? C13 C14 C15 O17 -0.5(3) . . . . ? C13 C14 C15 C7 179.74(16) . . . . ? C8 C7 C15 O17 -17.2(2) . . . . ? C12 C7 C15 O17 162.82(17) . . . . ? C8 C7 C15 C14 162.55(17) . . . . ? C12 C7 C15 C14 -17.4(3) . . . . ? #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_dbmrt_cu _database_code_depnum_ccdc_archive 'CCDC 739597' _audit_creation_date 2009-03-29T18:26:39-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; dibenzoylmethane ; _chemical_formula_sum 'C15 H12 O2' _chemical_formula_weight 224.25 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 8.7669(6) _cell_length_b 10.8752(8) _cell_length_c 24.5043(18) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2336.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ; ? ; _exptl_crystal_description block _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_colour white #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.673 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _cell_measurement_reflns_used 10321 _cell_measurement_theta_min 13.47 _cell_measurement_theta_max 144.32 _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54186 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; 'Rigaku R-AXIS RAPID IP Image Plate diffractometer' ; _diffrn_measurement_method \w _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_unetI/netI 0.0173 _diffrn_reflns_number 18611 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 6.73 _diffrn_reflns_theta_max 72.10 _diffrn_reflns_theta_full 72.10 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _reflns_number_total 2273 _reflns_number_gt 1580 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Farrugia, 1997), Mercury (McRae, 2006)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0379P)^2^+0.3453P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0026(2) _refine_ls_number_reflns 2273 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0586 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.1096 _refine_ls_wR_factor_gt 0.0870 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.099 _refine_diff_density_min -0.113 _refine_diff_density_rms 0.027 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' 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 0.18822(17) 0.94335(14) 0.51887(6) 0.0582(4) Uani 1 1 d . . . C2 C 0.0858(2) 0.87841(17) 0.55189(8) 0.0702(5) Uani 1 1 d . . . C3 C 0.0435(2) 0.92439(19) 0.60215(8) 0.0782(5) Uani 1 1 d . . . C4 C 0.0998(2) 1.03490(19) 0.62032(8) 0.0767(5) Uani 1 1 d . . . C5 C 0.1992(2) 1.10008(19) 0.58800(7) 0.0748(5) Uani 1 1 d . . . C6 C 0.2435(2) 1.05513(17) 0.53783(6) 0.0663(4) Uani 1 1 d . . . C7 C 0.47011(18) 0.96627(15) 0.33827(6) 0.0602(4) Uani 1 1 d . . . C8 C 0.5251(2) 0.89690(19) 0.29458(7) 0.0726(5) Uani 1 1 d . . . C9 C 0.6237(2) 0.9482(2) 0.25722(7) 0.0834(6) Uani 1 1 d . . . C10 C 0.6679(2) 1.0694(2) 0.26195(7) 0.0847(6) Uani 1 1 d . . . C11 C 0.6141(2) 1.1391(2) 0.30488(7) 0.0802(5) Uani 1 1 d . . . C12 C 0.5167(2) 1.08813(17) 0.34305(7) 0.0691(5) Uani 1 1 d . . . C13 C 0.23060(18) 0.89413(15) 0.46453(6) 0.0616(4) Uani 1 1 d . . . C14 C 0.33312(18) 0.95428(16) 0.42915(6) 0.0619(4) Uani 1 1 d . . . C15 C 0.36437(18) 0.90830(14) 0.37773(6) 0.0605(4) Uani 1 1 d . . . O16 O 0.16913(14) 0.79194(10) 0.44988(5) 0.0791(4) Uani 1 1 d . . . O17 O 0.29964(15) 0.80638(11) 0.36105(5) 0.0802(4) Uani 1 1 d . . . H18 H 0.046(2) 0.8015(16) 0.5373(7) 0.085(6) Uiso 1 1 d . . . H19 H -0.027(2) 0.8781(17) 0.6248(8) 0.093(6) Uiso 1 1 d . . . H20 H 0.069(2) 1.0670(16) 0.6575(7) 0.090(6) Uiso 1 1 d . . . H21 H 0.239(2) 1.1800(18) 0.6001(7) 0.088(6) Uiso 1 1 d . . . H22 H 0.3119(18) 1.1047(14) 0.5148(6) 0.073(5) Uiso 1 1 d . . . H23 H 0.4912(19) 0.8113(17) 0.2915(7) 0.082(6) Uiso 1 1 d . . . H24 H 0.661(2) 0.8978(17) 0.2277(8) 0.101(6) Uiso 1 1 d . . . H25 H 0.738(2) 1.1100(17) 0.2355(8) 0.100(6) Uiso 1 1 d . . . H26 H 0.644(2) 1.2269(18) 0.3087(7) 0.093(6) Uiso 1 1 d . . . H27 H 0.4808(18) 1.1379(15) 0.3742(7) 0.075(5) Uiso 1 1 d . . . H28 H 0.3811(18) 1.0313(15) 0.4409(6) 0.072(5) Uiso 1 1 d . . . H29 H 0.225(3) 0.779(2) 0.4029(11) 0.146(8) 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 C1 0.0549(9) 0.0588(10) 0.0609(9) 0.0121(7) -0.0048(7) 0.0032(7) C2 0.0661(11) 0.0623(11) 0.0822(12) 0.0134(9) 0.0022(9) -0.0019(9) C3 0.0710(12) 0.0844(14) 0.0791(12) 0.0211(10) 0.0150(9) 0.0011(10) C4 0.0773(12) 0.0875(14) 0.0654(10) 0.0077(10) 0.0095(9) 0.0022(10) C5 0.0819(12) 0.0795(13) 0.0630(10) 0.0028(9) 0.0064(9) -0.0102(10) C6 0.0676(10) 0.0719(11) 0.0595(9) 0.0082(8) 0.0032(8) -0.0084(9) C7 0.0618(9) 0.0649(10) 0.0539(8) -0.0025(7) -0.0058(7) 0.0109(8) C8 0.0760(11) 0.0796(13) 0.0621(10) -0.0141(9) -0.0058(9) 0.0079(10) C9 0.0835(13) 0.1074(17) 0.0592(10) -0.0179(11) 0.0019(9) 0.0144(12) C10 0.0833(13) 0.1076(17) 0.0630(11) 0.0013(11) 0.0101(9) 0.0038(12) C11 0.0917(14) 0.0782(14) 0.0706(11) 0.0025(10) 0.0110(10) 0.0022(11) C12 0.0784(11) 0.0697(12) 0.0591(9) -0.0015(8) 0.0068(8) 0.0110(9) C13 0.0625(10) 0.0556(10) 0.0666(9) 0.0067(7) -0.0092(8) 0.0038(8) C14 0.0636(10) 0.0602(10) 0.0620(9) -0.0008(8) -0.0001(7) -0.0023(8) C15 0.0647(10) 0.0538(9) 0.0631(9) -0.0015(7) -0.0103(7) 0.0075(8) O16 0.0941(9) 0.0631(8) 0.0801(8) 0.0040(6) -0.0045(7) -0.0124(6) O17 0.1000(9) 0.0649(8) 0.0758(8) -0.0080(6) -0.0052(7) -0.0053(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 C6 1.389(2) . ? C1 C2 1.400(2) . ? C1 C13 1.482(2) . ? C2 C3 1.380(3) . ? C2 H18 0.974(17) . ? C3 C4 1.373(3) . ? C3 H19 0.974(19) . ? C4 C5 1.374(2) . ? C4 H20 1.011(18) . ? C5 C6 1.379(2) . ? C5 H21 0.983(19) . ? C6 H22 0.985(16) . ? C7 C8 1.396(2) . ? C7 C12 1.392(2) . ? C7 C15 1.480(2) . ? C8 C9 1.377(3) . ? C8 H23 0.980(18) . ? C9 C10 1.378(3) . ? C9 H24 0.964(19) . ? C10 C11 1.380(3) . ? C10 H25 0.99(2) . ? C11 C12 1.383(2) . ? C11 H26 0.993(19) . ? C12 H27 0.987(16) . ? C13 O16 1.2862(18) . ? C13 C14 1.410(2) . ? C14 C15 1.383(2) . ? C14 H28 0.981(16) . ? C15 O17 1.3106(18) . ? O16 H29 1.26(3) . ? O17 H29 1.25(3) . ? 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 C6 C1 C2 118.16(16) . . ? C6 C1 C13 121.95(14) . . ? C2 C1 C13 119.86(16) . . ? C3 C2 C1 120.36(18) . . ? C3 C2 H18 122.8(11) . . ? C1 C2 H18 116.8(10) . . ? C2 C3 C4 120.66(18) . . ? C2 C3 H19 119.5(11) . . ? C4 C3 H19 119.8(11) . . ? C5 C4 C3 119.49(18) . . ? C5 C4 H20 120.5(11) . . ? C3 C4 H20 120.0(11) . . ? C6 C5 C4 120.64(19) . . ? C6 C5 H21 118.8(10) . . ? C4 C5 H21 120.6(10) . . ? C5 C6 C1 120.68(16) . . ? C5 C6 H22 119.3(9) . . ? C1 C6 H22 119.9(9) . . ? C8 C7 C12 118.55(16) . . ? C8 C7 C15 119.15(16) . . ? C12 C7 C15 122.30(14) . . ? C9 C8 C7 120.50(19) . . ? C9 C8 H23 121.6(10) . . ? C7 C8 H23 117.9(10) . . ? C8 C9 C10 120.54(19) . . ? C8 C9 H24 118.6(11) . . ? C10 C9 H24 120.8(11) . . ? C11 C10 C9 119.6(2) . . ? C11 C10 H25 117.6(11) . . ? C9 C10 H25 122.9(11) . . ? C12 C11 C10 120.4(2) . . ? C12 C11 H26 118.8(11) . . ? C10 C11 H26 120.8(11) . . ? C11 C12 C7 120.43(17) . . ? C11 C12 H27 120.0(10) . . ? C7 C12 H27 119.6(10) . . ? O16 C13 C14 119.76(15) . . ? O16 C13 C1 117.24(15) . . ? C14 C13 C1 123.00(15) . . ? C15 C14 C13 121.25(16) . . ? C15 C14 H28 119.5(9) . . ? C13 C14 H28 119.3(9) . . ? O17 C15 C14 120.27(15) . . ? O17 C15 C7 115.32(14) . . ? C14 C15 C7 124.41(15) . . ? C13 O16 H29 101.0(11) . . ? C15 O17 H29 100.0(11) . . ? 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 C6 C1 C2 C3 -0.9(2) . . . . ? C13 C1 C2 C3 -178.89(15) . . . . ? C1 C2 C3 C4 0.7(3) . . . . ? C2 C3 C4 C5 0.0(3) . . . . ? C3 C4 C5 C6 -0.5(3) . . . . ? C4 C5 C6 C1 0.3(3) . . . . ? C2 C1 C6 C5 0.4(2) . . . . ? C13 C1 C6 C5 178.39(15) . . . . ? C12 C7 C8 C9 0.2(2) . . . . ? C15 C7 C8 C9 -179.96(15) . . . . ? C7 C8 C9 C10 -0.9(3) . . . . ? C8 C9 C10 C11 0.7(3) . . . . ? C9 C10 C11 C12 0.2(3) . . . . ? C10 C11 C12 C7 -0.8(3) . . . . ? C8 C7 C12 C11 0.6(2) . . . . ? C15 C7 C12 C11 -179.16(15) . . . . ? C6 C1 C13 O16 -177.58(14) . . . . ? C2 C1 C13 O16 0.3(2) . . . . ? C6 C1 C13 C14 2.2(2) . . . . ? C2 C1 C13 C14 -179.87(14) . . . . ? O16 C13 C14 C15 2.8(2) . . . . ? C1 C13 C14 C15 -176.98(14) . . . . ? C13 C14 C15 O17 -0.6(2) . . . . ? C13 C14 C15 C7 179.84(14) . . . . ? C8 C7 C15 O17 -16.9(2) . . . . ? C12 C7 C15 O17 162.86(15) . . . . ? C8 C7 C15 C14 162.60(15) . . . . ? C12 C7 C15 C14 -17.6(2) . . . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF