# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2007 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'V. Bertolasi' 'V. Ferretti' 'Paola Gilli' 'Chao-Jun Li.' 'Xiaoquan Yao.' _publ_contact_author_name 'Valerio Bertolasi' _publ_contact_author_address ; Department of Chemistry University of Ferrara Via L.Borsari 46 - Ferrara Ferrara I-44100 ITALY ; _publ_contact_author_email M38@DNS.UNIFE.IT _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Substituent effects on keto-enol tautomerization of beta-diketones from X-ray structural data ; data_(1) _database_code_depnum_ccdc_archive 'CCDC 670942' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-[1-(4-chlorophenyl)ethyl]pentane-2,4-dione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H15 Cl O2' _chemical_formula_weight 238.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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' _cell_length_a 5.3281(2) _cell_length_b 8.3677(3) _cell_length_c 28.9434(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1290.41(9) _cell_formula_units_Z 4 _cell_measurement_temperature 295 _cell_measurement_reflns_used 1651 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 26.00 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.229 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.280 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7896 _diffrn_reflns_av_R_equivalents 0.0620 _diffrn_reflns_av_sigmaI/netI 0.0560 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2459 _reflns_number_gt 1484 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III (Burnett & Johnson, 1996)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995) ; _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^)+(0.0750P)^2^+0.0189P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.40(12) _refine_ls_number_reflns 2459 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0995 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1411 _refine_ls_wR_factor_gt 0.1183 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 Cl1 Cl 0.7667(2) 0.57423(12) 0.43369(3) 0.1008(4) Uani 1 1 d . . . O1 O 1.1826(4) 0.6303(3) 0.65479(9) 0.0970(8) Uani 1 1 d . . . O2 O 1.0204(7) 0.3535(5) 0.72586(9) 0.1394(13) Uani 1 1 d . . . C1 C 0.9599(7) 0.6418(4) 0.65942(9) 0.0644(8) Uani 1 1 d . . . C2 C 0.7959(7) 0.4951(4) 0.66817(10) 0.0657(8) Uani 1 1 d . . . C3 C 0.8436(7) 0.4371(5) 0.71707(11) 0.0800(10) Uani 1 1 d . . . C4 C 0.8336(7) 0.7988(4) 0.65813(12) 0.0867(10) Uani 1 1 d . . . H41 H 0.9575 0.8821 0.6577 0.104 Uiso 1 1 calc R . . H42 H 0.7295 0.8104 0.6850 0.104 Uiso 1 1 calc R . . H43 H 0.7318 0.8058 0.6308 0.104 Uiso 1 1 calc R . . C5 C 0.6692(7) 0.4962(5) 0.75344(12) 0.1010(13) Uani 1 1 d . . . H51 H 0.6995 0.4394 0.7817 0.121 Uiso 1 1 calc R . . H52 H 0.4990 0.4790 0.7438 0.121 Uiso 1 1 calc R . . H53 H 0.6966 0.6083 0.7583 0.121 Uiso 1 1 calc R . . C6 C 0.8431(7) 0.3631(4) 0.63258(11) 0.0707(9) Uani 1 1 d . . . C7 C 0.6666(9) 0.2217(4) 0.63996(13) 0.1047(13) Uani 1 1 d . . . H71 H 0.4963 0.2557 0.6353 0.126 Uiso 1 1 calc R . . H72 H 0.6857 0.1820 0.6709 0.126 Uiso 1 1 calc R . . H73 H 0.7067 0.1386 0.6183 0.126 Uiso 1 1 calc R . . C8 C 0.8254(5) 0.4213(3) 0.58319(10) 0.0583(7) Uani 1 1 d . . . C9 C 0.9983(6) 0.3717(4) 0.55078(11) 0.0726(9) Uani 1 1 d . . . C10 C 0.9815(7) 0.4160(4) 0.50486(11) 0.0763(9) Uani 1 1 d . . . C11 C 0.7905(7) 0.5132(3) 0.49117(10) 0.0668(8) Uani 1 1 d . . . C12 C 0.6142(7) 0.5651(4) 0.52238(12) 0.0724(9) Uani 1 1 d . . . C13 C 0.6335(7) 0.5173(4) 0.56806(11) 0.0690(9) Uani 1 1 d . . . H2 H 0.619(6) 0.511(3) 0.6646(9) 0.065(9) Uiso 1 1 d . . . H6 H 1.026(8) 0.324(4) 0.6396(12) 0.104(12) Uiso 1 1 d . . . H9 H 1.133(6) 0.304(3) 0.5594(10) 0.072(9) Uiso 1 1 d . . . H10 H 1.111(7) 0.383(4) 0.4851(12) 0.082(10) Uiso 1 1 d . . . H12 H 0.484(6) 0.621(4) 0.5127(10) 0.071(10) Uiso 1 1 d . . . H13 H 0.512(5) 0.543(3) 0.5895(10) 0.064(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 Cl1 0.1356(9) 0.1101(7) 0.0567(5) 0.0063(4) -0.0055(5) -0.0161(7) O1 0.0579(14) 0.123(2) 0.1102(19) -0.0113(16) 0.0021(13) 0.0049(14) O2 0.149(3) 0.195(3) 0.0742(17) 0.0229(19) -0.0129(18) 0.084(3) C1 0.066(2) 0.085(2) 0.0431(16) -0.0078(15) -0.0030(14) 0.0060(19) C2 0.058(2) 0.085(2) 0.0541(18) 0.0007(15) -0.0027(14) 0.0116(18) C3 0.084(2) 0.096(2) 0.060(2) 0.0104(18) -0.0056(17) 0.015(2) C4 0.101(2) 0.082(2) 0.077(2) 0.0029(17) -0.002(2) 0.012(2) C5 0.104(3) 0.133(3) 0.065(2) 0.009(2) 0.0173(19) -0.002(3) C6 0.076(2) 0.073(2) 0.063(2) 0.0036(16) -0.0062(16) 0.0152(19) C7 0.152(4) 0.075(2) 0.087(3) 0.013(2) -0.005(2) -0.004(3) C8 0.0574(17) 0.0575(16) 0.0599(17) -0.0054(14) -0.0063(14) 0.0069(16) C9 0.0646(19) 0.085(2) 0.068(2) -0.0084(18) -0.0062(18) 0.018(2) C10 0.071(2) 0.094(2) 0.064(2) -0.0145(19) 0.0092(19) 0.003(2) C11 0.080(2) 0.0684(18) 0.0520(17) -0.0010(14) -0.0056(16) -0.0098(19) C12 0.076(2) 0.073(2) 0.068(2) 0.0010(18) -0.0096(18) 0.0132(19) C13 0.072(2) 0.082(2) 0.0535(19) -0.0053(17) 0.0033(16) 0.0126(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C11 1.745(3) . ? O1 C1 1.198(4) . ? O2 C3 1.201(4) . ? C1 C4 1.476(4) . ? C1 C2 1.528(5) . ? C2 C3 1.518(4) . ? C2 C6 1.531(4) . ? C2 H2 0.96(3) . ? C3 C5 1.489(5) . ? C4 H41 0.9600 . ? C4 H42 0.9600 . ? C4 H43 0.9600 . ? C5 H51 0.9600 . ? C5 H52 0.9600 . ? C5 H53 0.9600 . ? C6 C8 1.513(4) . ? C6 C7 1.527(5) . ? C6 H6 1.05(4) . ? C7 H71 0.9600 . ? C7 H72 0.9600 . ? C7 H73 0.9600 . ? C8 C13 1.372(4) . ? C8 C9 1.379(4) . ? C9 C10 1.383(5) . ? C9 H9 0.95(3) . ? C10 C11 1.362(5) . ? C10 H10 0.94(3) . ? C11 C12 1.373(5) . ? C12 C13 1.385(5) . ? C12 H12 0.89(3) . ? C13 H13 0.92(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 O1 C1 C4 121.3(3) . . ? O1 C1 C2 121.3(3) . . ? C4 C1 C2 117.3(3) . . ? C3 C2 C1 108.4(3) . . ? C3 C2 C6 111.7(3) . . ? C1 C2 C6 112.0(3) . . ? C3 C2 H2 108.0(16) . . ? C1 C2 H2 115.5(18) . . ? C6 C2 H2 101.1(17) . . ? O2 C3 C5 122.2(3) . . ? O2 C3 C2 121.0(3) . . ? C5 C3 C2 116.6(3) . . ? C1 C4 H41 109.5 . . ? C1 C4 H42 109.5 . . ? H41 C4 H42 109.5 . . ? C1 C4 H43 109.5 . . ? H41 C4 H43 109.5 . . ? H42 C4 H43 109.5 . . ? C3 C5 H51 109.5 . . ? C3 C5 H52 109.5 . . ? H51 C5 H52 109.5 . . ? C3 C5 H53 109.5 . . ? H51 C5 H53 109.5 . . ? H52 C5 H53 109.5 . . ? C8 C6 C7 110.1(3) . . ? C8 C6 C2 113.2(3) . . ? C7 C6 C2 111.3(3) . . ? C8 C6 H6 110(2) . . ? C7 C6 H6 108(2) . . ? C2 C6 H6 104(2) . . ? C6 C7 H71 109.5 . . ? C6 C7 H72 109.5 . . ? H71 C7 H72 109.5 . . ? C6 C7 H73 109.5 . . ? H71 C7 H73 109.5 . . ? H72 C7 H73 109.5 . . ? C13 C8 C9 117.2(3) . . ? C13 C8 C6 122.5(3) . . ? C9 C8 C6 120.3(3) . . ? C8 C9 C10 122.0(3) . . ? C8 C9 H9 120.5(18) . . ? C10 C9 H9 117.5(18) . . ? C11 C10 C9 119.2(3) . . ? C11 C10 H10 123(2) . . ? C9 C10 H10 117(2) . . ? C10 C11 C12 120.6(3) . . ? C10 C11 Cl1 120.4(3) . . ? C12 C11 Cl1 119.0(3) . . ? C11 C12 C13 119.1(4) . . ? C11 C12 H12 120(2) . . ? C13 C12 H12 121(2) . . ? C8 C13 C12 121.9(3) . . ? C8 C13 H13 116.4(17) . . ? C12 C13 H13 121.5(17) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.140 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.042 ##END===== data_(2) _database_code_depnum_ccdc_archive 'CCDC 670943' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-[1-(4-chlorophenyl)ethyl]-1-phenylbutane-1,3-dione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 Cl O2' _chemical_formula_sum 'C18 H17 Cl O2' _chemical_formula_weight 300.77 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 15.3369(7) _cell_length_b 5.5988(2) _cell_length_c 19.0061(11) _cell_angle_alpha 90.00 _cell_angle_beta 109.104(2) _cell_angle_gamma 90.00 _cell_volume 1542.14(13) _cell_formula_units_Z 4 _cell_measurement_temperature 295 _cell_measurement_reflns_used 3260 _cell_measurement_theta_min 3.36 _cell_measurement_theta_max 26.00 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.249 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5343 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0606 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3025 _reflns_number_gt 1716 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995) ; _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^)+(0.0567P)^2^+0.2008P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3025 _refine_ls_number_parameters 258 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1078 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1328 _refine_ls_wR_factor_gt 0.1082 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 Cl1 Cl 0.03342(5) 0.19448(16) -0.08471(4) 0.0894(3) Uani 1 1 d . . . O1 O 0.41001(17) -0.3107(4) 0.33511(10) 0.0989(8) Uani 1 1 d . . . O2 O 0.19208(17) -0.3675(4) 0.26077(13) 0.1004(7) Uani 1 1 d . . . C1 C 0.36083(19) -0.1530(4) 0.34576(13) 0.0602(7) Uani 1 1 d . . . C2 C 0.29019(17) -0.0291(4) 0.27979(13) 0.0536(6) Uani 1 1 d . . . C3 C 0.19764(19) -0.1558(5) 0.26848(13) 0.0607(7) Uani 1 1 d . . . C4 C 0.36583(16) -0.0916(4) 0.42320(12) 0.0487(6) Uani 1 1 d . . . C5 C 0.32827(17) 0.1159(4) 0.44218(14) 0.0519(6) Uani 1 1 d . . . C6 C 0.33696(18) 0.1598(5) 0.51561(14) 0.0581(7) Uani 1 1 d . . . C7 C 0.38316(18) 0.0022(5) 0.57111(16) 0.0594(7) Uani 1 1 d . . . C8 C 0.42110(18) -0.2017(5) 0.55277(15) 0.0604(7) Uani 1 1 d . . . C9 C 0.41195(18) -0.2472(4) 0.47972(14) 0.0549(6) Uani 1 1 d . . . C10 C 0.1175(3) -0.0109(8) 0.2709(2) 0.0825(9) Uani 1 1 d . . . C11 C 0.32041(18) -0.0405(5) 0.21013(13) 0.0574(7) Uani 1 1 d . . . C12 C 0.4044(2) 0.1233(7) 0.2210(2) 0.0787(9) Uani 1 1 d . . . C13 C 0.24450(17) 0.0166(4) 0.13811(12) 0.0508(6) Uani 1 1 d . . . C14 C 0.1942(2) 0.2281(4) 0.12706(15) 0.0643(7) Uani 1 1 d . . . C15 C 0.1287(2) 0.2813(5) 0.05955(15) 0.0650(7) Uani 1 1 d . . . C16 C 0.11355(18) 0.1232(5) 0.00136(13) 0.0604(7) Uani 1 1 d . . . C17 C 0.16147(19) -0.0864(5) 0.01030(15) 0.0627(7) Uani 1 1 d . . . C18 C 0.22669(19) -0.1387(4) 0.07849(14) 0.0563(6) Uani 1 1 d . . . H9 H 0.4352(17) -0.381(5) 0.4658(14) 0.070(8) Uiso 1 1 d . . . H8 H 0.4535(18) -0.309(4) 0.5919(14) 0.073(8) Uiso 1 1 d . . . H11 H 0.3408(17) -0.205(4) 0.2078(13) 0.067(7) Uiso 1 1 d . . . H7 H 0.3884(15) 0.027(4) 0.6192(13) 0.047(6) Uiso 1 1 d . . . H15 H 0.0946(18) 0.416(5) 0.0553(14) 0.072(8) Uiso 1 1 d . . . H5 H 0.2986(16) 0.225(4) 0.4046(13) 0.055(7) Uiso 1 1 d . . . H2 H 0.2844(16) 0.135(5) 0.2929(13) 0.065(7) Uiso 1 1 d . . . H18 H 0.2612(17) -0.286(4) 0.0880(13) 0.065(7) Uiso 1 1 d . . . H6 H 0.3119(18) 0.301(5) 0.5268(14) 0.072(8) Uiso 1 1 d . . . H17 H 0.1511(19) -0.199(5) -0.0296(16) 0.082(8) Uiso 1 1 d . . . H14 H 0.2053(19) 0.343(5) 0.1655(15) 0.082(8) Uiso 1 1 d . . . H121 H 0.456(2) 0.074(6) 0.270(2) 0.115(12) Uiso 1 1 d . . . H122 H 0.424(2) 0.121(5) 0.1783(18) 0.089(10) Uiso 1 1 d . . . H101 H 0.062(3) -0.097(6) 0.2663(18) 0.113(12) Uiso 1 1 d . . . H123 H 0.387(2) 0.291(6) 0.2313(16) 0.090(10) Uiso 1 1 d . . . H102 H 0.106(2) 0.108(6) 0.237(2) 0.109(13) Uiso 1 1 d . . . H103 H 0.137(3) 0.070(7) 0.317(2) 0.140(16) 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 Cl1 0.0764(5) 0.1248(7) 0.0599(5) 0.0177(4) 0.0127(4) -0.0108(4) O1 0.1400(19) 0.0953(14) 0.0614(13) 0.0007(10) 0.0330(13) 0.0615(14) O2 0.1296(19) 0.0671(13) 0.128(2) -0.0279(12) 0.0734(16) -0.0264(12) C1 0.0792(18) 0.0536(14) 0.0493(15) -0.0008(11) 0.0231(14) 0.0121(13) C2 0.0698(17) 0.0487(14) 0.0433(14) -0.0057(10) 0.0199(12) 0.0034(12) C3 0.0815(19) 0.0628(16) 0.0419(14) -0.0073(11) 0.0257(13) -0.0046(14) C4 0.0515(14) 0.0483(12) 0.0462(14) 0.0003(10) 0.0160(11) -0.0002(11) C5 0.0546(15) 0.0476(14) 0.0502(16) -0.0002(11) 0.0128(12) 0.0036(11) C6 0.0603(16) 0.0579(15) 0.0549(16) -0.0131(12) 0.0171(13) 0.0024(13) C7 0.0598(17) 0.0720(17) 0.0451(16) -0.0067(13) 0.0153(13) -0.0046(13) C8 0.0612(17) 0.0664(16) 0.0494(16) 0.0089(13) 0.0124(13) 0.0039(13) C9 0.0582(16) 0.0528(14) 0.0541(16) 0.0002(12) 0.0188(13) 0.0052(12) C10 0.068(2) 0.101(3) 0.080(3) 0.004(2) 0.0263(19) 0.001(2) C11 0.0693(17) 0.0561(15) 0.0491(15) -0.0046(11) 0.0226(13) 0.0035(13) C12 0.071(2) 0.098(3) 0.070(2) -0.0058(18) 0.0265(18) -0.0143(18) C13 0.0657(16) 0.0481(13) 0.0441(14) -0.0028(10) 0.0256(12) -0.0062(11) C14 0.091(2) 0.0493(14) 0.0537(17) -0.0055(12) 0.0254(15) -0.0023(14) C15 0.078(2) 0.0541(15) 0.0641(19) 0.0069(13) 0.0255(16) 0.0026(14) C16 0.0638(17) 0.0721(17) 0.0475(15) 0.0065(12) 0.0211(13) -0.0118(14) C17 0.0754(19) 0.0684(17) 0.0494(16) -0.0127(13) 0.0275(15) -0.0114(15) C18 0.0683(17) 0.0548(14) 0.0517(16) -0.0038(12) 0.0279(14) -0.0034(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C16 1.741(3) . ? O1 C1 1.220(3) . ? O2 C3 1.194(3) . ? C1 C4 1.489(3) . ? C1 C2 1.529(3) . ? C2 C3 1.538(4) . ? C2 C11 1.541(3) . ? C2 H2 0.96(2) . ? C3 C10 1.486(4) . ? C4 C9 1.384(3) . ? C4 C5 1.396(3) . ? C5 C6 1.380(3) . ? C5 H5 0.94(2) . ? C6 C7 1.380(4) . ? C6 H6 0.93(3) . ? C7 C8 1.377(4) . ? C7 H7 0.90(2) . ? C8 C9 1.373(4) . ? C8 H8 0.96(3) . ? C9 H9 0.91(3) . ? C10 H101 0.96(4) . ? C10 H102 0.90(3) . ? C10 H103 0.94(4) . ? C11 C13 1.513(3) . ? C11 C12 1.539(4) . ? C11 H11 0.98(2) . ? C12 H121 1.04(3) . ? C12 H122 0.95(3) . ? C12 H123 1.01(3) . ? C13 C18 1.383(3) . ? C13 C14 1.391(3) . ? C14 C15 1.379(4) . ? C14 H14 0.95(3) . ? C15 C16 1.375(4) . ? C15 H15 0.91(3) . ? C16 C17 1.365(4) . ? C17 C18 1.385(4) . ? C17 H17 0.96(3) . ? C18 H18 0.97(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 O1 C1 C4 119.8(2) . . ? O1 C1 C2 120.2(2) . . ? C4 C1 C2 120.0(2) . . ? C1 C2 C3 106.2(2) . . ? C1 C2 C11 110.7(2) . . ? C3 C2 C11 112.60(19) . . ? C1 C2 H2 108.7(14) . . ? C3 C2 H2 108.4(15) . . ? C11 C2 H2 110.0(14) . . ? O2 C3 C10 121.3(3) . . ? O2 C3 C2 120.1(3) . . ? C10 C3 C2 118.6(3) . . ? C9 C4 C5 118.2(2) . . ? C9 C4 C1 118.0(2) . . ? C5 C4 C1 123.8(2) . . ? C6 C5 C4 119.9(2) . . ? C6 C5 H5 121.1(14) . . ? C4 C5 H5 119.0(14) . . ? C7 C6 C5 121.0(2) . . ? C7 C6 H6 120.9(16) . . ? C5 C6 H6 118.0(16) . . ? C8 C7 C6 119.4(3) . . ? C8 C7 H7 118.6(13) . . ? C6 C7 H7 122.0(13) . . ? C9 C8 C7 119.9(3) . . ? C9 C8 H8 121.5(15) . . ? C7 C8 H8 118.6(15) . . ? C8 C9 C4 121.7(3) . . ? C8 C9 H9 122.0(16) . . ? C4 C9 H9 116.3(16) . . ? C3 C10 H101 116(2) . . ? C3 C10 H102 111(2) . . ? H101 C10 H102 110(3) . . ? C3 C10 H103 106(2) . . ? H101 C10 H103 109(3) . . ? H102 C10 H103 103(3) . . ? C13 C11 C12 111.0(2) . . ? C13 C11 C2 114.2(2) . . ? C12 C11 C2 109.5(2) . . ? C13 C11 H11 108.7(14) . . ? C12 C11 H11 107.6(15) . . ? C2 C11 H11 105.5(15) . . ? C11 C12 H121 108.4(18) . . ? C11 C12 H122 111.0(17) . . ? H121 C12 H122 114(3) . . ? C11 C12 H123 108.8(18) . . ? H121 C12 H123 104(2) . . ? H122 C12 H123 110(3) . . ? C18 C13 C14 117.4(2) . . ? C18 C13 C11 119.7(2) . . ? C14 C13 C11 122.8(2) . . ? C15 C14 C13 121.6(2) . . ? C15 C14 H14 117.5(16) . . ? C13 C14 H14 120.9(16) . . ? C16 C15 C14 119.3(3) . . ? C16 C15 H15 121.5(17) . . ? C14 C15 H15 119.1(17) . . ? C17 C16 C15 120.7(3) . . ? C17 C16 Cl1 120.0(2) . . ? C15 C16 Cl1 119.3(2) . . ? C16 C17 C18 119.5(2) . . ? C16 C17 H17 121.6(16) . . ? C18 C17 H17 118.9(16) . . ? C13 C18 C17 121.5(2) . . ? C13 C18 H18 115.8(14) . . ? C17 C18 H18 122.7(14) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.246 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.036 ##END== data_(3) _database_code_depnum_ccdc_archive 'CCDC 670944' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-[1-(2-chlorophenyl)ethyl]-1-phenylbutane-1.3-dione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 Cl O2' _chemical_formula_sum 'C18 H17 Cl O2' _chemical_formula_weight 300.77 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P bca' 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 7.1662(2) _cell_length_b 11.4546(3) _cell_length_c 38.4210(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3153.83(16) _cell_formula_units_Z 8 _cell_measurement_temperature 295 _cell_measurement_reflns_used 3482 _cell_measurement_theta_min 4.14 _cell_measurement_theta_max 26.00 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.244 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5340 _diffrn_reflns_av_R_equivalents 0.0538 _diffrn_reflns_av_sigmaI/netI 0.0787 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -46 _diffrn_reflns_limit_l_max 46 _diffrn_reflns_theta_min 4.14 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3009 _reflns_number_gt 1506 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST(Nardelli, 1995) ; _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^)+(0.0406P)^2^+0.5225P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3009 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1375 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1243 _refine_ls_wR_factor_gt 0.0955 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.59407(13) 0.25339(6) 0.711088(19) 0.0973(4) Uani 1 1 d . . . O1 O 0.8491(3) 0.25613(17) 0.59859(5) 0.0981(7) Uani 1 1 d . . . O2 O 0.3583(3) 0.0460(2) 0.58983(5) 0.1094(8) Uani 1 1 d . . . C1 C 0.7841(4) 0.1658(2) 0.58719(6) 0.0640(7) Uani 1 1 d . . . C2 C 0.6637(4) 0.0881(3) 0.61052(6) 0.0617(7) Uani 1 1 d . . . C3 C 0.4592(4) 0.1165(3) 0.60353(6) 0.0725(8) Uani 1 1 d . . . C4 C 0.8078(3) 0.13625(19) 0.54982(6) 0.0521(6) Uani 1 1 d . . . C5 C 0.7255(4) 0.0393(2) 0.53427(7) 0.0602(7) Uani 1 1 d . . . C6 C 0.7402(4) 0.0208(3) 0.49899(7) 0.0611(7) Uani 1 1 d . . . C7 C 0.8383(4) 0.0978(3) 0.47874(8) 0.0670(8) Uani 1 1 d . . . C8 C 0.9233(4) 0.1929(3) 0.49383(8) 0.0694(8) Uani 1 1 d . . . C9 C 0.9098(4) 0.2114(2) 0.52877(8) 0.0616(7) Uani 1 1 d . . . C10 C 0.3893(4) 0.2339(3) 0.61388(8) 0.0950(10) Uani 1 1 d . . . H101 H 0.2698 0.2474 0.6033 0.114 Uiso 1 1 calc R . . H102 H 0.4757 0.2925 0.6062 0.114 Uiso 1 1 calc R . . H103 H 0.3774 0.2374 0.6387 0.114 Uiso 1 1 calc R . . C11 C 0.7200(4) 0.1020(3) 0.64894(6) 0.0654(7) Uani 1 1 d . . . C12 C 0.9114(5) 0.0486(4) 0.65582(11) 0.0957(11) Uani 1 1 d . . . C13 C 0.5771(4) 0.0522(2) 0.67378(6) 0.0603(7) Uani 1 1 d . . . C14 C 0.5081(5) -0.0607(3) 0.66980(8) 0.0777(9) Uani 1 1 d . . . C15 C 0.3816(5) -0.1084(3) 0.69272(9) 0.0875(10) Uani 1 1 d . . . C16 C 0.3199(5) -0.0455(4) 0.72021(9) 0.0883(10) Uani 1 1 d . . . C17 C 0.3852(5) 0.0654(4) 0.72542(8) 0.0845(10) Uani 1 1 d . . . C18 C 0.5127(4) 0.1123(2) 0.70247(6) 0.0666(7) Uani 1 1 d . . . H2 H 0.680(3) 0.013(2) 0.6043(5) 0.054(7) Uiso 1 1 d . . . H5 H 0.655(3) -0.0073(19) 0.5475(5) 0.060(7) Uiso 1 1 d . . . H6 H 0.685(4) -0.047(2) 0.4888(6) 0.074(8) Uiso 1 1 d . . . H7 H 0.844(3) 0.0836(19) 0.4549(6) 0.066(8) Uiso 1 1 d . . . H8 H 0.999(4) 0.244(2) 0.4805(6) 0.074(8) Uiso 1 1 d . . . H9 H 0.963(3) 0.2725(18) 0.5397(5) 0.050(7) Uiso 1 1 d . . . H11 H 0.724(3) 0.186(2) 0.6530(5) 0.062(7) Uiso 1 1 d . . . H14 H 0.551(3) -0.098(2) 0.6524(6) 0.068(8) Uiso 1 1 d . . . H15 H 0.338(4) -0.184(3) 0.6885(7) 0.103(11) Uiso 1 1 d . . . H16 H 0.226(4) -0.074(2) 0.7355(7) 0.098(10) Uiso 1 1 d . . . H17 H 0.348(4) 0.109(2) 0.7436(7) 0.091(10) Uiso 1 1 d . . . H121 H 0.959(5) 0.067(3) 0.6789(9) 0.127(13) Uiso 1 1 d . . . H122 H 0.914(5) -0.040(3) 0.6528(9) 0.135(15) Uiso 1 1 d . . . H123 H 1.001(4) 0.077(2) 0.6407(7) 0.102(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 Cl1 0.1362(8) 0.0765(5) 0.0793(5) -0.0207(4) -0.0122(5) 0.0112(5) O1 0.1365(19) 0.0768(13) 0.0811(12) -0.0183(10) 0.0108(12) -0.0442(13) O2 0.0824(16) 0.1382(19) 0.1076(16) -0.0283(14) -0.0107(12) -0.0285(14) C1 0.0678(19) 0.0579(16) 0.0664(16) -0.0039(13) 0.0011(14) -0.0060(14) C2 0.069(2) 0.0562(17) 0.0596(16) -0.0030(14) 0.0022(13) -0.0051(15) C3 0.077(2) 0.088(2) 0.0522(15) -0.0020(14) -0.0001(15) -0.0129(18) C4 0.0489(16) 0.0464(14) 0.0608(14) 0.0023(12) 0.0024(12) 0.0000(12) C5 0.0619(18) 0.0571(16) 0.0618(16) 0.0022(14) 0.0069(15) -0.0074(14) C6 0.0560(17) 0.0631(17) 0.0642(16) -0.0048(15) 0.0016(15) -0.0019(15) C7 0.0605(19) 0.080(2) 0.0604(18) 0.0023(16) 0.0056(15) 0.0111(16) C8 0.064(2) 0.0682(19) 0.076(2) 0.0092(17) 0.0154(16) -0.0032(16) C9 0.0557(17) 0.0524(16) 0.0765(19) -0.0036(14) 0.0049(15) -0.0036(14) C10 0.088(2) 0.106(2) 0.092(2) 0.0074(18) -0.0088(17) 0.0178(19) C11 0.072(2) 0.0626(18) 0.0620(15) -0.0047(14) -0.0025(15) -0.0006(15) C12 0.070(3) 0.128(4) 0.089(3) 0.013(3) -0.001(2) 0.004(2) C13 0.0682(18) 0.0610(17) 0.0516(14) 0.0000(13) -0.0056(14) 0.0050(14) C14 0.089(2) 0.074(2) 0.0698(19) -0.0089(18) 0.0087(18) -0.0015(18) C15 0.094(3) 0.083(2) 0.086(2) 0.006(2) 0.0078(19) -0.011(2) C16 0.082(3) 0.111(3) 0.072(2) 0.019(2) 0.0071(18) -0.001(2) C17 0.091(3) 0.109(3) 0.0536(17) -0.0012(19) 0.0078(18) 0.024(2) C18 0.077(2) 0.0676(17) 0.0547(15) -0.0041(13) -0.0106(15) 0.0131(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C18 1.749(3) . ? O1 C1 1.217(3) . ? O2 C3 1.205(3) . ? C1 C4 1.485(3) . ? C1 C2 1.529(4) . ? C2 C3 1.525(4) . ? C2 C11 1.538(3) . ? C2 H2 0.90(2) . ? C3 C10 1.488(4) . ? C4 C9 1.389(3) . ? C4 C5 1.392(3) . ? C5 C6 1.376(3) . ? C5 H5 0.89(2) . ? C6 C7 1.370(4) . ? C6 H6 0.95(2) . ? C7 C8 1.376(4) . ? C7 H7 0.93(2) . ? C8 C9 1.363(4) . ? C8 H8 0.94(3) . ? C9 H9 0.90(2) . ? C10 H101 0.9600 . ? C10 H102 0.9600 . ? C10 H103 0.9600 . ? C11 C13 1.512(3) . ? C11 C12 1.525(4) . ? C11 H11 0.98(2) . ? C12 H121 0.97(4) . ? C12 H122 1.02(3) . ? C12 H123 0.92(3) . ? C13 C18 1.380(3) . ? C13 C14 1.393(4) . ? C14 C15 1.377(4) . ? C14 H14 0.85(2) . ? C15 C16 1.353(4) . ? C15 H15 0.93(3) . ? C16 C17 1.369(4) . ? C16 H16 0.95(3) . ? C17 C18 1.379(4) . ? C17 H17 0.90(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 O1 C1 C4 119.9(2) . . ? O1 C1 C2 120.0(2) . . ? C4 C1 C2 119.9(2) . . ? C3 C2 C1 108.3(2) . . ? C3 C2 C11 113.5(2) . . ? C1 C2 C11 110.8(2) . . ? C3 C2 H2 106.2(14) . . ? C1 C2 H2 109.1(14) . . ? C11 C2 H2 108.8(14) . . ? O2 C3 C10 121.3(3) . . ? O2 C3 C2 120.7(3) . . ? C10 C3 C2 118.0(3) . . ? C9 C4 C5 117.9(2) . . ? C9 C4 C1 118.8(2) . . ? C5 C4 C1 123.2(2) . . ? C6 C5 C4 120.9(3) . . ? C6 C5 H5 120.8(14) . . ? C4 C5 H5 118.1(14) . . ? C7 C6 C5 119.9(3) . . ? C7 C6 H6 120.1(14) . . ? C5 C6 H6 120.0(14) . . ? C6 C7 C8 119.9(3) . . ? C6 C7 H7 117.9(14) . . ? C8 C7 H7 122.2(14) . . ? C9 C8 C7 120.5(3) . . ? C9 C8 H8 118.5(15) . . ? C7 C8 H8 120.9(14) . . ? C8 C9 C4 121.0(3) . . ? C8 C9 H9 123.3(13) . . ? C4 C9 H9 115.7(13) . . ? C3 C10 H101 109.5 . . ? C3 C10 H102 109.5 . . ? H101 C10 H102 109.5 . . ? C3 C10 H103 109.5 . . ? H101 C10 H103 109.5 . . ? H102 C10 H103 109.5 . . ? C13 C11 C12 110.4(3) . . ? C13 C11 C2 112.9(2) . . ? C12 C11 C2 111.2(3) . . ? C13 C11 H11 107.1(12) . . ? C12 C11 H11 110.0(13) . . ? C2 C11 H11 105.2(12) . . ? C11 C12 H121 113(2) . . ? C11 C12 H122 113(2) . . ? H121 C12 H122 108(3) . . ? C11 C12 H123 112.2(19) . . ? H121 C12 H123 105(3) . . ? H122 C12 H123 105(3) . . ? C18 C13 C14 115.6(3) . . ? C18 C13 C11 122.9(2) . . ? C14 C13 C11 121.4(2) . . ? C15 C14 C13 122.1(3) . . ? C15 C14 H14 123.0(17) . . ? C13 C14 H14 114.9(17) . . ? C16 C15 C14 120.2(4) . . ? C16 C15 H15 121.3(19) . . ? C14 C15 H15 118.5(19) . . ? C15 C16 C17 119.8(3) . . ? C15 C16 H16 122.3(16) . . ? C17 C16 H16 117.8(16) . . ? C16 C17 C18 119.6(3) . . ? C16 C17 H17 121.8(17) . . ? C18 C17 H17 118.6(17) . . ? C17 C18 C13 122.6(3) . . ? C17 C18 Cl1 117.4(2) . . ? C13 C18 Cl1 120.1(2) . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.158 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.032 ##END== data_(4) _database_code_depnum_ccdc_archive 'CCDC 670945' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-diphenyl-2-(1-phenylethyl)propane-1,3-dione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H20 O2' _chemical_formula_sum 'C23 H20 O2' _chemical_formula_weight 328.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P bca' 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 16.9980(2) _cell_length_b 9.9242(3) _cell_length_c 21.5231(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3630.77(14) _cell_formula_units_Z 8 _cell_measurement_temperature 295 _cell_measurement_reflns_used 5398 _cell_measurement_theta_min 3.68 _cell_measurement_theta_max 27.00 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.202 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7329 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0334 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.68 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3938 _reflns_number_gt 2709 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995) ; _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^)+(0.0604P)^2^+0.8406P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3938 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0776 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1354 _refine_ls_wR_factor_gt 0.1184 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.83274(7) -0.14766(14) 0.35336(7) 0.0721(4) Uani 1 1 d . . . O2 O 0.65841(7) -0.23011(11) 0.36618(6) 0.0626(4) Uani 1 1 d . . . C1 C 0.78885(9) -0.06408(17) 0.37591(8) 0.0501(4) Uani 1 1 d . . . C2 C 0.71516(8) -0.01948(15) 0.34095(7) 0.0407(3) Uani 1 1 d . . . C3 C 0.64845(9) -0.10845(15) 0.36663(7) 0.0437(4) Uani 1 1 d . . . C4 C 0.80307(10) -0.01090(18) 0.43983(8) 0.0562(5) Uani 1 1 d . . . C5 C 0.75593(13) 0.0843(3) 0.46781(9) 0.0719(6) Uani 1 1 d . . . C6 C 0.77127(17) 0.1283(3) 0.52778(11) 0.0972(9) Uani 1 1 d . . . C7 C 0.8355(2) 0.0737(4) 0.55936(13) 0.1157(12) Uani 1 1 d . . . C8 C 0.8842(3) -0.0180(4) 0.53064(17) 0.1263(13) Uani 1 1 d . . . C9 C 0.86852(17) -0.0611(3) 0.47142(13) 0.0932(8) Uani 1 1 d . . . C10 C 0.57317(9) -0.05120(16) 0.38977(7) 0.0467(4) Uani 1 1 d . . . C11 C 0.54933(11) 0.07990(19) 0.37799(9) 0.0599(5) Uani 1 1 d . . . C12 C 0.47572(13) 0.1232(3) 0.39714(11) 0.0790(6) Uani 1 1 d . . . C13 C 0.42614(13) 0.0374(3) 0.42846(11) 0.0797(6) Uani 1 1 d . . . C14 C 0.44990(13) -0.0910(3) 0.44158(10) 0.0767(6) Uani 1 1 d . . . C15 C 0.52280(11) -0.1362(2) 0.42237(9) 0.0615(5) Uani 1 1 d . . . C16 C 0.72174(8) -0.04315(16) 0.26979(7) 0.0428(4) Uani 1 1 d . . . C17 C 0.79321(11) 0.0277(2) 0.24144(10) 0.0611(5) Uani 1 1 d . . . C18 C 0.64533(9) -0.00201(15) 0.23875(6) 0.0408(3) Uani 1 1 d . . . C19 C 0.58784(9) -0.09648(17) 0.22526(7) 0.0465(4) Uani 1 1 d . . . C20 C 0.51680(10) -0.0579(2) 0.19905(8) 0.0565(4) Uani 1 1 d . . . C21 C 0.50253(11) 0.0747(2) 0.18557(8) 0.0593(5) Uani 1 1 d . . . C22 C 0.55877(11) 0.1697(2) 0.19860(8) 0.0610(5) Uani 1 1 d . . . C23 C 0.62962(11) 0.13212(17) 0.22515(8) 0.0532(4) Uani 1 1 d . . . H2 H 0.7045(8) 0.0759(15) 0.3483(6) 0.032(4) Uiso 1 1 d . . . H5 H 0.7121(13) 0.120(2) 0.4478(10) 0.083(7) Uiso 1 1 d . . . H6 H 0.7393(12) 0.201(2) 0.5424(11) 0.081(7) Uiso 1 1 d . . . H7 H 0.8409(18) 0.107(3) 0.5993(16) 0.135(11) Uiso 1 1 d . . . H8 H 0.937(2) -0.052(3) 0.5517(16) 0.149(11) Uiso 1 1 d . . . H9 H 0.9055(17) -0.137(3) 0.4490(13) 0.136(11) Uiso 1 1 d . . . H11 H 0.5855(11) 0.141(2) 0.3549(9) 0.070(5) Uiso 1 1 d . . . H12 H 0.4615(15) 0.215(3) 0.3886(11) 0.107(8) Uiso 1 1 d . . . H13 H 0.3743(15) 0.072(2) 0.4416(11) 0.089(7) Uiso 1 1 d . . . H14 H 0.4144(15) -0.151(2) 0.4640(11) 0.105(8) Uiso 1 1 d . . . H15 H 0.5430(11) -0.231(2) 0.4318(9) 0.075(6) Uiso 1 1 d . . . H16 H 0.7292(9) -0.1408(16) 0.2641(7) 0.043(4) Uiso 1 1 d . . . H171 H 0.7931(13) 0.019(2) 0.1964(11) 0.086(7) Uiso 1 1 d . . . H172 H 0.8444(14) -0.015(2) 0.2557(10) 0.085(6) Uiso 1 1 d . . . H173 H 0.7962(14) 0.126(3) 0.2534(12) 0.101(8) Uiso 1 1 d . . . H19 H 0.5974(9) -0.1901(18) 0.2341(7) 0.050(4) Uiso 1 1 d . . . H20 H 0.4792(11) -0.1245(19) 0.1912(9) 0.070(6) Uiso 1 1 d . . . H21 H 0.4547(12) 0.0998(19) 0.1678(9) 0.071(6) Uiso 1 1 d . . . H22 H 0.5497(11) 0.264(2) 0.1901(9) 0.066(5) Uiso 1 1 d . . . H23 H 0.6670(11) 0.2032(19) 0.2351(8) 0.064(5) 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 O1 0.0514(7) 0.0798(9) 0.0851(10) 0.0023(7) -0.0093(7) 0.0224(7) O2 0.0615(8) 0.0450(7) 0.0814(9) 0.0099(6) -0.0007(6) -0.0007(5) C1 0.0393(8) 0.0518(9) 0.0591(10) 0.0091(7) -0.0077(7) -0.0019(7) C2 0.0355(8) 0.0399(8) 0.0466(8) 0.0010(6) -0.0048(6) 0.0012(6) C3 0.0424(8) 0.0463(9) 0.0423(8) 0.0053(6) -0.0075(7) -0.0018(7) C4 0.0489(10) 0.0651(11) 0.0547(10) 0.0141(8) -0.0146(8) -0.0157(9) C5 0.0572(12) 0.1081(16) 0.0505(10) -0.0038(10) -0.0094(9) -0.0166(12) C6 0.0838(17) 0.146(3) 0.0624(14) -0.0194(15) -0.0039(12) -0.0336(18) C7 0.129(3) 0.161(3) 0.0565(15) 0.0074(17) -0.0366(16) -0.062(2) C8 0.145(3) 0.134(3) 0.100(2) 0.017(2) -0.078(2) -0.013(2) C9 0.0939(17) 0.0908(17) 0.0948(17) 0.0124(13) -0.0539(15) -0.0023(14) C10 0.0438(8) 0.0551(9) 0.0411(8) -0.0004(7) -0.0024(7) -0.0064(7) C11 0.0503(10) 0.0665(11) 0.0630(11) 0.0121(9) 0.0113(8) 0.0074(9) C12 0.0612(12) 0.0908(16) 0.0850(15) 0.0160(12) 0.0174(11) 0.0204(12) C13 0.0517(12) 0.1093(19) 0.0780(14) -0.0045(12) 0.0166(10) 0.0019(12) C14 0.0643(13) 0.0914(16) 0.0744(14) -0.0065(11) 0.0217(11) -0.0228(12) C15 0.0628(11) 0.0634(12) 0.0582(10) -0.0042(8) 0.0093(9) -0.0152(9) C16 0.0365(8) 0.0447(9) 0.0472(8) -0.0022(6) -0.0024(6) 0.0021(6) C17 0.0439(10) 0.0788(14) 0.0607(12) 0.0029(10) 0.0055(8) -0.0047(9) C18 0.0396(8) 0.0466(8) 0.0364(7) -0.0020(6) -0.0002(6) 0.0021(7) C19 0.0419(8) 0.0482(9) 0.0493(9) -0.0005(7) -0.0006(7) -0.0009(7) C20 0.0411(9) 0.0724(12) 0.0560(10) -0.0018(8) -0.0027(8) -0.0031(9) C21 0.0447(10) 0.0816(13) 0.0516(10) 0.0034(9) -0.0055(8) 0.0146(9) C22 0.0664(12) 0.0577(11) 0.0588(11) 0.0052(8) -0.0074(9) 0.0158(9) C23 0.0568(10) 0.0486(10) 0.0543(9) 0.0009(7) -0.0094(8) 0.0013(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.217(2) . ? O2 C3 1.2192(18) . ? C1 C4 1.493(2) . ? C1 C2 1.527(2) . ? C2 C3 1.540(2) . ? C2 C16 1.554(2) . ? C2 H2 0.977(14) . ? C3 C10 1.486(2) . ? C4 C5 1.378(3) . ? C4 C9 1.396(3) . ? C5 C6 1.387(3) . ? C5 H5 0.93(2) . ? C6 C7 1.396(5) . ? C6 H6 0.96(2) . ? C7 C8 1.377(5) . ? C7 H7 0.93(3) . ? C8 C9 1.370(4) . ? C8 H8 1.06(4) . ? C9 H9 1.10(3) . ? C10 C11 1.386(2) . ? C10 C15 1.392(2) . ? C11 C12 1.386(3) . ? C11 H11 1.00(2) . ? C12 C13 1.375(3) . ? C12 H12 0.96(3) . ? C13 C14 1.367(3) . ? C13 H13 0.99(2) . ? C14 C15 1.381(3) . ? C14 H14 0.98(2) . ? C15 H15 1.02(2) . ? C16 C18 1.516(2) . ? C16 C17 1.531(2) . ? C16 H16 0.985(16) . ? C17 H171 0.97(2) . ? C17 H172 1.01(2) . ? C17 H173 1.01(2) . ? C18 C19 1.385(2) . ? C18 C23 1.389(2) . ? C19 C20 1.387(2) . ? C19 H19 0.962(17) . ? C20 C21 1.369(3) . ? C20 H20 0.935(19) . ? C21 C22 1.371(3) . ? C21 H21 0.93(2) . ? C22 C23 1.384(2) . ? C22 H22 0.96(2) . ? C23 H23 0.974(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C4 120.61(15) . . ? O1 C1 C2 120.28(15) . . ? C4 C1 C2 118.97(15) . . ? C1 C2 C3 105.14(12) . . ? C1 C2 C16 112.52(13) . . ? C3 C2 C16 108.67(12) . . ? C1 C2 H2 110.8(8) . . ? C3 C2 H2 111.1(8) . . ? C16 C2 H2 108.6(8) . . ? O2 C3 C10 120.07(14) . . ? O2 C3 C2 117.56(14) . . ? C10 C3 C2 122.36(13) . . ? C5 C4 C9 119.7(2) . . ? C5 C4 C1 123.44(16) . . ? C9 C4 C1 116.9(2) . . ? C4 C5 C6 120.9(2) . . ? C4 C5 H5 121.6(14) . . ? C6 C5 H5 117.5(14) . . ? C5 C6 C7 118.6(3) . . ? C5 C6 H6 115.9(14) . . ? C7 C6 H6 125.3(14) . . ? C8 C7 C6 120.5(3) . . ? C8 C7 H7 126(2) . . ? C6 C7 H7 113(2) . . ? C9 C8 C7 120.5(3) . . ? C9 C8 H8 117.7(19) . . ? C7 C8 H8 121.6(19) . . ? C8 C9 C4 119.8(3) . . ? C8 C9 H9 120.9(16) . . ? C4 C9 H9 119.3(16) . . ? C11 C10 C15 118.76(17) . . ? C11 C10 C3 123.33(15) . . ? C15 C10 C3 117.84(15) . . ? C12 C11 C10 120.07(19) . . ? C12 C11 H11 121.1(11) . . ? C10 C11 H11 118.9(11) . . ? C13 C12 C11 120.5(2) . . ? C13 C12 H12 121.8(16) . . ? C11 C12 H12 117.7(16) . . ? C14 C13 C12 119.9(2) . . ? C14 C13 H13 121.7(13) . . ? C12 C13 H13 118.5(13) . . ? C13 C14 C15 120.4(2) . . ? C13 C14 H14 119.2(14) . . ? C15 C14 H14 120.4(15) . . ? C14 C15 C10 120.4(2) . . ? C14 C15 H15 122.7(11) . . ? C10 C15 H15 116.8(11) . . ? C18 C16 C17 112.36(13) . . ? C18 C16 C2 109.39(12) . . ? C17 C16 C2 112.38(14) . . ? C18 C16 H16 108.7(9) . . ? C17 C16 H16 107.4(9) . . ? C2 C16 H16 106.3(9) . . ? C16 C17 H171 110.7(13) . . ? C16 C17 H172 111.7(12) . . ? H171 C17 H172 105.2(18) . . ? C16 C17 H173 112.5(14) . . ? H171 C17 H173 110.0(19) . . ? H172 C17 H173 106.3(19) . . ? C19 C18 C23 117.96(14) . . ? C19 C18 C16 120.96(14) . . ? C23 C18 C16 121.04(14) . . ? C18 C19 C20 120.85(16) . . ? C18 C19 H19 119.6(9) . . ? C20 C19 H19 119.6(9) . . ? C21 C20 C19 120.39(17) . . ? C21 C20 H20 121.3(12) . . ? C19 C20 H20 118.3(12) . . ? C20 C21 C22 119.57(17) . . ? C20 C21 H21 119.9(12) . . ? C22 C21 H21 120.6(12) . . ? C21 C22 C23 120.41(17) . . ? C21 C22 H22 121.0(11) . . ? C23 C22 H22 118.6(11) . . ? C22 C23 C18 120.82(17) . . ? C22 C23 H23 117.7(11) . . ? C18 C23 H23 121.5(11) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.203 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.036 ##END== data_(5) _database_code_depnum_ccdc_archive 'CCDC 670946' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-[1-(2-chlorophenyl)ethyl]-1,3-diphenylpropane-1,3-dione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H19 Cl O2' _chemical_formula_sum 'C23 H19 Cl O2' _chemical_formula_weight 362.83 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 11.1539(3) _cell_length_b 16.3314(6) _cell_length_c 11.4618(3) _cell_angle_alpha 90.00 _cell_angle_beta 114.694(1) _cell_angle_gamma 90.00 _cell_volume 1896.94(10) _cell_formula_units_Z 4 _cell_measurement_temperature 295 _cell_measurement_reflns_used 5263 _cell_measurement_theta_min 3.87 _cell_measurement_theta_max 27.00 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.270 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7619 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_sigmaI/netI 0.0456 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.87 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4126 _reflns_number_gt 2652 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST (Nardelli) ; _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^)+(0.0569P)^2^+0.5064P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4126 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0889 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1396 _refine_ls_wR_factor_gt 0.1179 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 Cl1 Cl 0.44597(10) 0.09452(6) 0.56327(8) 0.1212(4) Uani 1 1 d . . . O1 O 0.35410(18) 0.31570(10) 0.71276(14) 0.0768(5) Uani 1 1 d . . . O2 O 0.63517(13) 0.27556(9) 0.97480(14) 0.0612(4) Uani 1 1 d . . . C1 C 0.36895(18) 0.30826(12) 0.82310(18) 0.0485(4) Uani 1 1 d . . . C2 C 0.41540(17) 0.22681(11) 0.89360(16) 0.0420(4) Uani 1 1 d . . . C3 C 0.55281(17) 0.24111(11) 1.00151(17) 0.0457(4) Uani 1 1 d . . . C4 C 0.34804(17) 0.37954(11) 0.89391(18) 0.0473(4) Uani 1 1 d . . . C5 C 0.35324(19) 0.37349(13) 1.0168(2) 0.0522(5) Uani 1 1 d . . . C6 C 0.3410(2) 0.44330(15) 1.0800(3) 0.0667(6) Uani 1 1 d . . . C7 C 0.3243(2) 0.51841(16) 1.0217(3) 0.0746(7) Uani 1 1 d . . . C8 C 0.3165(3) 0.52470(15) 0.9000(3) 0.0781(7) Uani 1 1 d . . . C9 C 0.3275(2) 0.45591(13) 0.8361(3) 0.0665(6) Uani 1 1 d . . . C10 C 0.58595(17) 0.21369(11) 1.13534(17) 0.0468(4) Uani 1 1 d . . . C11 C 0.5032(2) 0.16451(14) 1.16821(19) 0.0584(5) Uani 1 1 d . . . C12 C 0.5395(3) 0.14051(18) 1.2944(2) 0.0776(7) Uani 1 1 d . . . C13 C 0.6572(3) 0.1665(2) 1.3881(3) 0.0892(9) Uani 1 1 d . . . C14 C 0.7397(3) 0.21500(19) 1.3567(3) 0.0869(8) Uani 1 1 d . . . C15 C 0.7062(2) 0.23813(15) 1.2312(2) 0.0651(6) Uani 1 1 d . . . C16 C 0.42589(19) 0.15901(12) 0.80405(18) 0.0485(5) Uani 1 1 d . . . C17 C 0.4775(3) 0.07903(14) 0.8781(2) 0.0619(6) Uani 1 1 d . . . C18 C 0.2979(2) 0.14125(12) 0.68925(18) 0.0537(5) Uani 1 1 d . . . C19 C 0.1747(2) 0.15043(15) 0.6908(2) 0.0619(6) Uani 1 1 d . . . C20 C 0.0590(3) 0.1287(2) 0.5882(2) 0.0906(8) Uani 1 1 d . . . C21 C 0.0628(4) 0.0978(2) 0.4793(3) 0.1129(11) Uani 1 1 d . . . C22 C 0.1803(5) 0.0885(2) 0.4724(3) 0.1084(12) Uani 1 1 d . . . C23 C 0.2979(3) 0.10936(15) 0.5766(2) 0.0770(7) Uani 1 1 d . . . H2 H 0.3545(18) 0.2124(11) 0.9276(17) 0.046(5) Uiso 1 1 d . . . H5 H 0.3629(18) 0.3205(13) 1.0567(18) 0.054(5) Uiso 1 1 d . . . H6 H 0.344(3) 0.4351(16) 1.161(3) 0.092(9) Uiso 1 1 d . . . H7 H 0.317(2) 0.5660(17) 1.066(2) 0.086(8) Uiso 1 1 d . . . H8 H 0.306(3) 0.5791(18) 0.858(3) 0.097(8) Uiso 1 1 d . . . H9 H 0.322(2) 0.4597(16) 0.750(2) 0.085(8) Uiso 1 1 d . . . H11 H 0.419(2) 0.1483(14) 1.104(2) 0.067(6) Uiso 1 1 d . . . H12 H 0.476(3) 0.1089(17) 1.314(3) 0.092(8) Uiso 1 1 d . . . H13 H 0.682(3) 0.1490(18) 1.475(3) 0.106(9) Uiso 1 1 d . . . H14 H 0.817(3) 0.2308(17) 1.416(3) 0.097(9) Uiso 1 1 d . . . H15 H 0.763(2) 0.2706(15) 1.205(2) 0.074(7) Uiso 1 1 d . . . H16 H 0.490(2) 0.1788(12) 0.7717(18) 0.059(6) Uiso 1 1 d . . . H171 H 0.566(3) 0.0866(16) 0.952(3) 0.088(8) Uiso 1 1 d . . . H172 H 0.482(2) 0.0391(16) 0.821(2) 0.079(7) Uiso 1 1 d . . . H173 H 0.413(2) 0.0567(14) 0.913(2) 0.074(7) Uiso 1 1 d . . . H19 H 0.1707(19) 0.1723(13) 0.766(2) 0.057(5) Uiso 1 1 d . . . H20 H -0.025(3) 0.137(2) 0.597(3) 0.132(12) Uiso 1 1 d . . . H21 H -0.029(4) 0.084(2) 0.405(3) 0.135(12) Uiso 1 1 d . . . H22 H 0.199(3) 0.070(2) 0.408(3) 0.119(10) 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 Cl1 0.1661(8) 0.1382(8) 0.1047(6) -0.0044(5) 0.1016(6) 0.0374(6) O1 0.1221(14) 0.0629(10) 0.0497(9) 0.0147(7) 0.0402(9) 0.0155(9) O2 0.0557(8) 0.0606(9) 0.0740(9) 0.0104(7) 0.0337(7) -0.0042(7) C1 0.0544(11) 0.0478(11) 0.0429(10) 0.0069(8) 0.0200(8) 0.0026(8) C2 0.0470(10) 0.0421(10) 0.0409(9) 0.0028(7) 0.0223(8) 0.0028(8) C3 0.0479(10) 0.0398(10) 0.0517(11) 0.0029(8) 0.0232(9) 0.0034(8) C4 0.0429(9) 0.0423(10) 0.0552(11) 0.0036(8) 0.0189(8) 0.0028(8) C5 0.0511(10) 0.0483(12) 0.0575(12) -0.0023(10) 0.0230(9) 0.0028(9) C6 0.0591(13) 0.0682(16) 0.0733(16) -0.0155(13) 0.0280(12) 0.0015(11) C7 0.0607(13) 0.0522(14) 0.111(2) -0.0234(15) 0.0355(14) -0.0012(11) C8 0.0787(16) 0.0429(13) 0.116(2) 0.0068(14) 0.0439(16) 0.0077(11) C9 0.0729(14) 0.0482(13) 0.0796(17) 0.0144(11) 0.0330(13) 0.0098(10) C10 0.0469(10) 0.0466(10) 0.0438(10) 0.0012(8) 0.0160(8) 0.0055(8) C11 0.0565(12) 0.0721(15) 0.0440(12) 0.0090(10) 0.0186(10) -0.0020(10) C12 0.0843(17) 0.0954(19) 0.0533(14) 0.0171(13) 0.0291(13) 0.0032(14) C13 0.100(2) 0.110(2) 0.0436(14) 0.0107(14) 0.0162(14) 0.0124(17) C14 0.0783(18) 0.095(2) 0.0563(16) -0.0035(14) -0.0028(14) 0.0020(15) C15 0.0573(13) 0.0631(14) 0.0612(14) -0.0008(11) 0.0113(11) -0.0011(11) C16 0.0575(11) 0.0478(11) 0.0482(11) 0.0008(8) 0.0299(9) 0.0059(9) C17 0.0705(15) 0.0470(12) 0.0654(15) 0.0005(11) 0.0256(13) 0.0133(11) C18 0.0775(13) 0.0459(11) 0.0434(11) 0.0001(8) 0.0309(10) 0.0058(9) C19 0.0657(13) 0.0764(15) 0.0404(11) -0.0070(10) 0.0191(10) -0.0002(11) C20 0.0810(18) 0.121(2) 0.0554(15) -0.0134(15) 0.0139(13) -0.0107(16) C21 0.117(3) 0.138(3) 0.0612(18) -0.0294(18) 0.0141(19) -0.016(2) C22 0.167(4) 0.105(2) 0.0523(17) -0.0298(15) 0.045(2) -0.002(2) C23 0.118(2) 0.0705(15) 0.0547(14) -0.0085(11) 0.0482(14) 0.0093(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C23 1.737(3) . ? O1 C1 1.211(2) . ? O2 C3 1.220(2) . ? C1 C4 1.492(3) . ? C1 C2 1.530(3) . ? C2 C3 1.533(3) . ? C2 C16 1.547(2) . ? C2 H2 0.943(19) . ? C3 C10 1.489(3) . ? C4 C9 1.386(3) . ? C4 C5 1.389(3) . ? C5 C6 1.388(3) . ? C5 H5 0.96(2) . ? C6 C7 1.372(4) . ? C6 H6 0.93(3) . ? C7 C8 1.364(4) . ? C7 H7 0.95(3) . ? C8 C9 1.375(3) . ? C8 H8 1.00(3) . ? C9 H9 0.97(3) . ? C10 C11 1.389(3) . ? C10 C15 1.390(3) . ? C11 C12 1.386(3) . ? C11 H11 0.95(2) . ? C12 C13 1.370(4) . ? C12 H12 0.97(3) . ? C13 C14 1.371(4) . ? C13 H13 0.96(3) . ? C14 C15 1.380(4) . ? C14 H14 0.89(3) . ? C15 H15 0.96(2) . ? C16 C18 1.511(3) . ? C16 C17 1.533(3) . ? C16 H16 0.99(2) . ? C17 H171 1.01(3) . ? C17 H172 0.94(3) . ? C17 H173 1.02(2) . ? C18 C19 1.390(3) . ? C18 C23 1.392(3) . ? C19 C20 1.381(3) . ? C19 H19 0.95(2) . ? C20 C21 1.364(4) . ? C20 H20 1.00(3) . ? C21 C22 1.354(5) . ? C21 H21 1.05(4) . ? C22 C23 1.399(4) . ? C22 H22 0.90(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 O1 C1 C4 120.37(17) . . ? O1 C1 C2 120.47(17) . . ? C4 C1 C2 119.10(15) . . ? C1 C2 C3 107.31(15) . . ? C1 C2 C16 112.00(14) . . ? C3 C2 C16 108.49(14) . . ? C1 C2 H2 106.9(11) . . ? C3 C2 H2 110.8(11) . . ? C16 C2 H2 111.3(11) . . ? O2 C3 C10 120.55(17) . . ? O2 C3 C2 118.14(16) . . ? C10 C3 C2 121.32(15) . . ? C9 C4 C5 118.54(19) . . ? C9 C4 C1 118.29(18) . . ? C5 C4 C1 123.12(17) . . ? C6 C5 C4 120.0(2) . . ? C6 C5 H5 120.4(12) . . ? C4 C5 H5 119.6(12) . . ? C7 C6 C5 120.2(3) . . ? C7 C6 H6 124.0(17) . . ? C5 C6 H6 115.8(17) . . ? C8 C7 C6 120.2(2) . . ? C8 C7 H7 119.9(16) . . ? C6 C7 H7 119.9(16) . . ? C7 C8 C9 120.1(2) . . ? C7 C8 H8 120.8(16) . . ? C9 C8 H8 119.0(16) . . ? C8 C9 C4 120.9(2) . . ? C8 C9 H9 120.8(16) . . ? C4 C9 H9 118.2(16) . . ? C11 C10 C15 118.85(19) . . ? C11 C10 C3 123.11(17) . . ? C15 C10 C3 118.04(18) . . ? C12 C11 C10 120.6(2) . . ? C12 C11 H11 119.5(13) . . ? C10 C11 H11 119.9(13) . . ? C13 C12 C11 119.8(3) . . ? C13 C12 H12 122.3(16) . . ? C11 C12 H12 117.8(16) . . ? C12 C13 C14 120.1(3) . . ? C12 C13 H13 119.3(18) . . ? C14 C13 H13 120.6(17) . . ? C13 C14 C15 120.8(3) . . ? C13 C14 H14 120.9(19) . . ? C15 C14 H14 118.2(19) . . ? C14 C15 C10 119.8(2) . . ? C14 C15 H15 123.0(14) . . ? C10 C15 H15 117.2(14) . . ? C18 C16 C17 108.54(17) . . ? C18 C16 C2 114.17(15) . . ? C17 C16 C2 110.94(16) . . ? C18 C16 H16 107.7(11) . . ? C17 C16 H16 108.9(12) . . ? C2 C16 H16 106.4(12) . . ? C16 C17 H171 111.9(15) . . ? C16 C17 H172 108.6(15) . . ? H171 C17 H172 111(2) . . ? C16 C17 H173 111.0(13) . . ? H171 C17 H173 108.5(19) . . ? H172 C17 H173 106.0(19) . . ? C19 C18 C23 115.8(2) . . ? C19 C18 C16 123.19(17) . . ? C23 C18 C16 120.9(2) . . ? C20 C19 C18 122.6(2) . . ? C20 C19 H19 119.1(12) . . ? C18 C19 H19 118.2(12) . . ? C21 C20 C19 119.9(3) . . ? C21 C20 H20 122(2) . . ? C19 C20 H20 118(2) . . ? C22 C21 C20 119.8(3) . . ? C22 C21 H21 124.8(19) . . ? C20 C21 H21 115.5(19) . . ? C21 C22 C23 120.6(3) . . ? C21 C22 H22 130(2) . . ? C23 C22 H22 109(2) . . ? C18 C23 C22 121.3(3) . . ? C18 C23 Cl1 120.1(2) . . ? C22 C23 Cl1 118.6(2) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.181 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.032 ##END== data_(6) _database_code_depnum_ccdc_archive 'CCDC 670947' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-diphenyl-1-(1-phenylpropyl)propane-1,3-dione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H22 O2' _chemical_formula_sum 'C24 H22 O2' _chemical_formula_weight 342.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P bca' 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 17.0267(4) _cell_length_b 9.9384(2) _cell_length_c 22.3568(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3783.18(17) _cell_formula_units_Z 8 _cell_measurement_temperature 295 _cell_measurement_reflns_used 4565 _cell_measurement_theta_min 3.62 _cell_measurement_theta_max 26.00 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.202 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6855 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0541 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3704 _reflns_number_gt 2146 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995) ; _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^)+(0.0578P)^2^+0.3141P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3704 _refine_ls_number_parameters 323 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1041 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1249 _refine_ls_wR_factor_gt 0.1027 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.32671(9) -0.15154(14) 0.36085(7) 0.0739(5) Uani 1 1 d . . . O2 O 0.15235(8) -0.22873(13) 0.36788(6) 0.0660(4) Uani 1 1 d . . . C1 C 0.28442(11) -0.06503(17) 0.38211(9) 0.0501(5) Uani 1 1 d . . . C2 C 0.21161(10) -0.01793(17) 0.34777(8) 0.0409(4) Uani 1 1 d . . . C3 C 0.14362(11) -0.10701(17) 0.37033(8) 0.0454(5) Uani 1 1 d . . . C4 C 0.30062(11) -0.01055(17) 0.44306(9) 0.0505(5) Uani 1 1 d . . . C5 C 0.25584(14) 0.0879(2) 0.46993(10) 0.0661(6) Uani 1 1 d . . . C6 C 0.27344(16) 0.1319(3) 0.52712(12) 0.0874(8) Uani 1 1 d . . . C7 C 0.33582(19) 0.0771(4) 0.55740(13) 0.0926(9) Uani 1 1 d . . . C8 C 0.3815(2) -0.0188(3) 0.53089(15) 0.1052(10) Uani 1 1 d . . . C9 C 0.36441(17) -0.0623(3) 0.47415(13) 0.0859(8) Uani 1 1 d . . . C10 C 0.06939(11) -0.04858(17) 0.39369(8) 0.0454(5) Uani 1 1 d . . . C11 C 0.05115(12) 0.0872(2) 0.38992(9) 0.0541(5) Uani 1 1 d . . . C12 C -0.01966(13) 0.1344(3) 0.41224(10) 0.0665(6) Uani 1 1 d . . . C13 C -0.07242(14) 0.0469(3) 0.43818(10) 0.0702(6) Uani 1 1 d . . . C14 C -0.05460(13) -0.0875(3) 0.44170(10) 0.0706(6) Uani 1 1 d . . . C15 C 0.01509(12) -0.1351(2) 0.41978(9) 0.0594(5) Uani 1 1 d . . . C16 C 0.21998(10) -0.03656(17) 0.27941(8) 0.0422(4) Uani 1 1 d . . . C17 C 0.29114(13) 0.0407(2) 0.25517(10) 0.0570(5) Uani 1 1 d . . . C18 C 0.3049(2) 0.0210(4) 0.18927(13) 0.0875(8) Uani 1 1 d . . . C19 C 0.14437(10) 0.00048(15) 0.24748(8) 0.0412(4) Uani 1 1 d . . . C20 C 0.09313(11) -0.09767(19) 0.22703(8) 0.0507(5) Uani 1 1 d . . . C21 C 0.02419(12) -0.0632(2) 0.19781(10) 0.0615(6) Uani 1 1 d . . . C22 C 0.00591(13) 0.0688(2) 0.18781(10) 0.0635(6) Uani 1 1 d . . . C23 C 0.05567(13) 0.1674(2) 0.20803(10) 0.0644(6) Uani 1 1 d . . . C24 C 0.12334(12) 0.13406(18) 0.23812(9) 0.0548(5) Uani 1 1 d . . . H2 H 0.2014(8) 0.0757(15) 0.3566(7) 0.032(4) Uiso 1 1 d . . . H5 H 0.2116(13) 0.1268(19) 0.4471(10) 0.081(7) Uiso 1 1 d . . . H6 H 0.2431(13) 0.205(2) 0.5437(11) 0.082(7) Uiso 1 1 d . . . H7 H 0.3451(14) 0.105(2) 0.5952(12) 0.091(8) Uiso 1 1 d . . . H8 H 0.4280(19) -0.054(3) 0.5503(14) 0.128(10) Uiso 1 1 d . . . H9 H 0.3945(15) -0.131(3) 0.4547(12) 0.105(9) Uiso 1 1 d . . . H11 H 0.0874(11) 0.1479(18) 0.3715(8) 0.054(5) Uiso 1 1 d . . . H12 H -0.0311(12) 0.228(2) 0.4092(10) 0.083(7) Uiso 1 1 d . . . H13 H -0.1217(15) 0.080(2) 0.4513(10) 0.084(7) Uiso 1 1 d . . . H14 H -0.0927(14) -0.150(2) 0.4588(10) 0.093(7) Uiso 1 1 d . . . H15 H 0.0306(11) -0.230(2) 0.4229(9) 0.078(7) Uiso 1 1 d . . . H16 H 0.2283(9) -0.1336(17) 0.2722(7) 0.043(4) Uiso 1 1 d . . . H171 H 0.2835(12) 0.140(2) 0.2638(10) 0.082(7) Uiso 1 1 d . . . H172 H 0.3398(15) 0.007(2) 0.2760(11) 0.091(8) Uiso 1 1 d . . . H181 H 0.264(2) 0.069(3) 0.1648(15) 0.130(12) Uiso 1 1 d . . . H182 H 0.3554(17) 0.064(3) 0.1752(13) 0.119(9) Uiso 1 1 d . . . H183 H 0.3059(15) -0.066(3) 0.1757(14) 0.109(10) Uiso 1 1 d . . . H20 H 0.1069(10) -0.1939(19) 0.2337(8) 0.056(5) Uiso 1 1 d . . . H21 H -0.0098(12) -0.135(2) 0.1858(10) 0.080(7) Uiso 1 1 d . . . H22 H -0.0428(13) 0.0921(19) 0.1679(10) 0.074(6) Uiso 1 1 d . . . H23 H 0.0437(11) 0.264(2) 0.2017(9) 0.078(6) Uiso 1 1 d . . . H24 H 0.1564(11) 0.2042(18) 0.2531(8) 0.058(5) 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 O1 0.0690(10) 0.0782(10) 0.0745(11) -0.0081(7) -0.0120(8) 0.0304(8) O2 0.0752(10) 0.0448(8) 0.0780(10) 0.0056(6) 0.0069(8) -0.0016(6) C1 0.0463(12) 0.0503(10) 0.0537(13) 0.0017(9) -0.0035(9) 0.0039(9) C2 0.0412(10) 0.0399(10) 0.0417(11) -0.0011(7) -0.0005(8) 0.0024(7) C3 0.0524(12) 0.0468(11) 0.0372(11) 0.0026(8) -0.0044(9) -0.0023(8) C4 0.0468(12) 0.0572(11) 0.0476(12) 0.0063(9) -0.0084(9) -0.0079(9) C5 0.0498(13) 0.0992(16) 0.0492(14) -0.0114(12) -0.0039(12) -0.0056(12) C6 0.0653(18) 0.135(2) 0.0621(18) -0.0274(16) -0.0019(14) -0.0152(16) C7 0.096(2) 0.132(2) 0.0503(18) -0.0011(16) -0.0206(16) -0.0441(19) C8 0.114(3) 0.110(2) 0.091(2) -0.0021(18) -0.061(2) 0.0038(19) C9 0.0899(19) 0.0815(17) 0.086(2) -0.0052(14) -0.0424(16) 0.0096(14) C10 0.0466(11) 0.0542(11) 0.0353(10) 0.0005(8) -0.0024(9) -0.0070(8) C11 0.0458(12) 0.0618(13) 0.0548(13) 0.0051(10) 0.0052(10) -0.0003(10) C12 0.0529(14) 0.0817(16) 0.0649(15) 0.0042(12) 0.0060(12) 0.0114(12) C13 0.0423(13) 0.113(2) 0.0554(15) -0.0033(13) 0.0018(11) 0.0015(13) C14 0.0546(15) 0.0982(18) 0.0590(15) 0.0020(12) 0.0070(12) -0.0221(13) C15 0.0577(14) 0.0698(14) 0.0507(13) -0.0020(10) 0.0038(11) -0.0152(11) C16 0.0412(11) 0.0418(10) 0.0437(11) -0.0024(8) -0.0002(8) 0.0011(7) C17 0.0473(13) 0.0695(13) 0.0542(14) -0.0006(10) 0.0042(11) -0.0057(10) C18 0.082(2) 0.117(2) 0.0639(19) -0.0018(17) 0.0259(16) -0.0138(18) C19 0.0427(11) 0.0447(10) 0.0362(10) -0.0001(7) 0.0033(9) -0.0006(8) C20 0.0493(12) 0.0499(11) 0.0530(13) -0.0005(9) 0.0001(10) -0.0030(9) C21 0.0475(13) 0.0767(15) 0.0604(14) -0.0002(11) -0.0060(11) -0.0101(11) C22 0.0493(13) 0.0859(16) 0.0551(14) 0.0124(11) -0.0034(12) 0.0127(12) C23 0.0685(15) 0.0610(13) 0.0638(15) 0.0077(11) -0.0020(12) 0.0160(11) C24 0.0601(14) 0.0475(11) 0.0568(14) -0.0019(9) -0.0070(11) 0.0022(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.218(2) . ? O2 C3 1.220(2) . ? C1 C4 1.492(3) . ? C1 C2 1.531(2) . ? C2 C3 1.542(2) . ? C2 C16 1.546(2) . ? C2 H2 0.967(15) . ? C3 C10 1.486(3) . ? C4 C5 1.378(3) . ? C4 C9 1.388(3) . ? C5 C6 1.384(3) . ? C5 H5 0.99(2) . ? C6 C7 1.372(4) . ? C6 H6 0.97(2) . ? C7 C8 1.365(4) . ? C7 H7 0.90(3) . ? C8 C9 1.371(4) . ? C8 H8 0.97(3) . ? C9 H9 0.95(3) . ? C10 C11 1.387(3) . ? C10 C15 1.391(3) . ? C11 C12 1.387(3) . ? C11 H11 0.956(19) . ? C12 C13 1.378(3) . ? C12 H12 0.95(2) . ? C13 C14 1.371(3) . ? C13 H13 0.95(2) . ? C14 C15 1.368(3) . ? C14 H14 0.97(2) . ? C15 H15 0.98(2) . ? C16 C19 1.517(2) . ? C16 C17 1.534(3) . ? C16 H16 0.988(16) . ? C17 C18 1.505(3) . ? C17 H171 1.01(2) . ? C17 H172 1.01(2) . ? C18 H181 1.01(3) . ? C18 H182 1.01(3) . ? C18 H183 0.92(3) . ? C19 C20 1.386(2) . ? C19 C24 1.391(2) . ? C20 C21 1.386(3) . ? C20 H20 0.996(18) . ? C21 C22 1.367(3) . ? C21 H21 0.96(2) . ? C22 C23 1.372(3) . ? C22 H22 0.97(2) . ? C23 C24 1.375(3) . ? C23 H23 0.99(2) . ? C24 H24 0.956(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C4 120.21(17) . . ? O1 C1 C2 119.91(17) . . ? C4 C1 C2 119.77(16) . . ? C1 C2 C3 105.56(14) . . ? C1 C2 C16 112.60(15) . . ? C3 C2 C16 108.89(14) . . ? C1 C2 H2 109.7(9) . . ? C3 C2 H2 110.5(9) . . ? C16 C2 H2 109.5(9) . . ? O2 C3 C10 120.46(16) . . ? O2 C3 C2 117.59(16) . . ? C10 C3 C2 121.94(15) . . ? C5 C4 C9 118.5(2) . . ? C5 C4 C1 123.60(17) . . ? C9 C4 C1 117.9(2) . . ? C4 C5 C6 120.5(2) . . ? C4 C5 H5 118.3(13) . . ? C6 C5 H5 121.2(13) . . ? C7 C6 C5 119.9(3) . . ? C7 C6 H6 121.5(14) . . ? C5 C6 H6 118.5(14) . . ? C8 C7 C6 120.2(3) . . ? C8 C7 H7 121.4(16) . . ? C6 C7 H7 118.3(16) . . ? C7 C8 C9 120.1(3) . . ? C7 C8 H8 121.4(18) . . ? C9 C8 H8 118.4(18) . . ? C8 C9 C4 120.8(3) . . ? C8 C9 H9 122.1(16) . . ? C4 C9 H9 117.1(16) . . ? C11 C10 C15 118.56(19) . . ? C11 C10 C3 123.31(16) . . ? C15 C10 C3 118.12(17) . . ? C12 C11 C10 120.1(2) . . ? C12 C11 H11 120.2(10) . . ? C10 C11 H11 119.7(10) . . ? C13 C12 C11 120.3(2) . . ? C13 C12 H12 120.8(13) . . ? C11 C12 H12 118.8(13) . . ? C14 C13 C12 119.6(2) . . ? C14 C13 H13 121.0(13) . . ? C12 C13 H13 119.3(13) . . ? C15 C14 C13 120.5(2) . . ? C15 C14 H14 119.9(13) . . ? C13 C14 H14 119.6(13) . . ? C14 C15 C10 120.9(2) . . ? C14 C15 H15 122.7(12) . . ? C10 C15 H15 116.4(12) . . ? C19 C16 C17 112.48(15) . . ? C19 C16 C2 110.97(14) . . ? C17 C16 C2 111.24(15) . . ? C19 C16 H16 106.4(9) . . ? C17 C16 H16 108.5(9) . . ? C2 C16 H16 107.0(9) . . ? C18 C17 C16 113.8(2) . . ? C18 C17 H171 109.5(13) . . ? C16 C17 H171 108.6(12) . . ? C18 C17 H172 106.3(14) . . ? C16 C17 H172 108.8(13) . . ? H171 C17 H172 109.7(17) . . ? C17 C18 H181 111.1(18) . . ? C17 C18 H182 112.5(17) . . ? H181 C18 H182 103(2) . . ? C17 C18 H183 116.7(19) . . ? H181 C18 H183 106(3) . . ? H182 C18 H183 106(2) . . ? C20 C19 C24 117.38(17) . . ? C20 C19 C16 121.22(14) . . ? C24 C19 C16 121.39(16) . . ? C21 C20 C19 120.98(18) . . ? C21 C20 H20 120.5(10) . . ? C19 C20 H20 118.5(10) . . ? C22 C21 C20 120.4(2) . . ? C22 C21 H21 122.1(12) . . ? C20 C21 H21 117.4(12) . . ? C21 C22 C23 119.4(2) . . ? C21 C22 H22 120.0(12) . . ? C23 C22 H22 120.6(12) . . ? C22 C23 C24 120.4(2) . . ? C22 C23 H23 121.2(12) . . ? C24 C23 H23 118.4(12) . . ? C23 C24 C19 121.30(19) . . ? C23 C24 H24 119.3(11) . . ? C19 C24 H24 119.4(11) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.126 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.032 ##END==