# Supplementary Material (ESI) for Physical Chemistry Chemical Physics # This journal is (c) The Owner Societies 2010 data_global _journal_name_full Phys.Chem.Chem.Phys.(PCCP) _journal_coden_cambridge 1326 #============================================================= _audit_creation_date 'June 3, 2008' _audit_creation_method 'from SHELXL-97 with Word-Perfect Macro PRPKAPPA' _audit_update_record ; June 3, 2008 Assembled, pass-1 2008-06-04 # Formatted by publCIF ; # 1. SUBMISSION DETAILS _publ_contact_author_name 'John Nicolson Low' _publ_contact_author_address ; Department of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen, AB24 3UE, Scotland. ; _publ_contact_author_email jnlow111@googlemail.com # 3. TITLE AND AUTHOR LIST _publ_section_title ; 1,3-diphenylpropan-2-one ; loop_ _publ_author_name _publ_author_footnote _publ_author_address C.F.Lima . ; Centro de Investiga\,c\~ao em Qu\'imica, Departamento de Qu\'imica, Faculdade de Ci\^encias, Universidade do Porto Rua do Campo Alegre, 687, P-4169_007 Porto Portugal ; J.N.Low . ; Department of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen, AB24 3UE, Scotland. ; L.R.Gomes . ; CIAGEB-Faculdade de Ci\^encias da Sa\'ude, Escola Superior de Sa\'ude da UFP, Universidade Fernando Pessoa Rua Carlos Maia, 296, P-4200_150 Porto Portugal ; L.M.N.B.F.Santos . ; Centro de Investiga\,c\~ao em Qu\'imica, Departamento de Qu\'imica, Faculdade de Ci\^encias, Universidade do Porto Rua do Campo Alegre, 687, P-4169_007 Porto Portugal ; _publ_section_exptl_refinement ; Molecule (1) crystallized in the monoclinic system; space group P21/c from the systematic absences. H atoms were treated as riding atoms with C---H(aromatic), 0.95 \%A. Reflection 002 omitted, obscured by beamstop. ; _publ_section_references ; Bruker (2004). Smart APEX (version 5.62), SAINT (Version 6.02), SHELXTL (Version 6.10) and SADABS (Version 2.03). Bruker AXS Inc., Madison, Wisconsin, USA. Johnson, C. K. & Burnett, M. N. (1998). ORTEPIII for Windows. University of Glasgow. Glasgow, U.K. Sheldrick, G. M. (1997). SHELXS-97 and SHELXL-97. University of G\"ottingen, Germany. Sheldrick, G. M. (2003). SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10 ; data_1 _database_code_depnum_ccdc_archive 'CCDC 735344' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-propan-2-one ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H14 O' _chemical_formula_sum 'C15 H14 O' _chemical_formula_weight 210.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.4756(2) _cell_length_b 5.65970(10) _cell_length_c 21.2859(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.4720(10) _cell_angle_gamma 90.00 _cell_volume 1134.27(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 30.62 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.231 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, G.M. 2003)' _exptl_absorpt_correction_T_min 0.9851 _exptl_absorpt_correction_T_max 0.9970 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% nil _diffrn_reflns_number 17359 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 30.62 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.62 _diffrn_measured_fraction_theta_full 0.997 _reflns_number_total 3485 _reflns_number_gt 2653 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'APEX2 and SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT and XPREP (Sheldrick, 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0558P)^2^+0.3232P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3485 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0630 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1189 _refine_ls_wR_factor_gt 0.1067 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.324 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.042 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 O2 O 0.46035(10) 0.86429(18) 0.68757(4) 0.0393(2) Uani 1 1 d . . . C1 C 0.69257(12) 0.7501(2) 0.73023(5) 0.0288(2) Uani 1 1 d . . . H1A H 0.6866 0.8945 0.7561 0.035 Uiso 1 1 calc R . . H1B H 0.7039 0.6135 0.7594 0.035 Uiso 1 1 calc R . . C2 C 0.55499(11) 0.7223(2) 0.68684(5) 0.0238(2) Uani 1 1 d . . . C3 C 0.54425(11) 0.5078(2) 0.64381(5) 0.0243(2) Uani 1 1 d . . . H3A H 0.6350 0.4909 0.6253 0.029 Uiso 1 1 calc R . . H3B H 0.5328 0.3657 0.6699 0.029 Uiso 1 1 calc R . . C11 C 0.82193(11) 0.76699(19) 0.69486(5) 0.0207(2) Uani 1 1 d . . . C12 C 0.84167(12) 0.9632(2) 0.65738(5) 0.0260(2) Uani 1 1 d . . . H12 H 0.7727 1.0857 0.6537 0.031 Uiso 1 1 calc R . . C13 C 0.96088(13) 0.9820(2) 0.62539(6) 0.0302(3) Uani 1 1 d . . . H13 H 0.9732 1.1173 0.6002 0.036 Uiso 1 1 calc R . . C14 C 1.06198(12) 0.8045(2) 0.63005(5) 0.0293(3) Uani 1 1 d . . . H14 H 1.1438 0.8176 0.6083 0.035 Uiso 1 1 calc R . . C15 C 1.04259(12) 0.6077(2) 0.66676(5) 0.0281(2) Uani 1 1 d . . . H15 H 1.1111 0.4846 0.6699 0.034 Uiso 1 1 calc R . . C16 C 0.92368(12) 0.5891(2) 0.69904(5) 0.0242(2) Uani 1 1 d . . . H16 H 0.9117 0.4535 0.7242 0.029 Uiso 1 1 calc R . . C31 C 0.42480(11) 0.51273(18) 0.59069(5) 0.0210(2) Uani 1 1 d . . . C32 C 0.32944(12) 0.32586(19) 0.58148(5) 0.0244(2) Uani 1 1 d . . . H32 H 0.3364 0.1970 0.6103 0.029 Uiso 1 1 calc R . . C33 C 0.22369(13) 0.3261(2) 0.53030(5) 0.0288(2) Uani 1 1 d . . . H33 H 0.1595 0.1970 0.5242 0.035 Uiso 1 1 calc R . . C34 C 0.21192(13) 0.5138(2) 0.48831(5) 0.0301(3) Uani 1 1 d . . . H34 H 0.1397 0.5141 0.4535 0.036 Uiso 1 1 calc R . . C35 C 0.30618(13) 0.7016(2) 0.49735(5) 0.0286(2) Uani 1 1 d . . . H35 H 0.2982 0.8312 0.4688 0.034 Uiso 1 1 calc R . . C36 C 0.41217(12) 0.7005(2) 0.54799(5) 0.0244(2) Uani 1 1 d . . . H36 H 0.4768 0.8291 0.5536 0.029 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0356(5) 0.0446(5) 0.0365(5) -0.0160(4) -0.0018(4) 0.0142(4) C1 0.0221(5) 0.0448(7) 0.0199(5) -0.0037(4) 0.0036(4) -0.0055(5) C2 0.0216(5) 0.0308(5) 0.0196(4) -0.0023(4) 0.0047(4) -0.0017(4) C3 0.0200(5) 0.0276(5) 0.0250(5) -0.0035(4) 0.0015(4) 0.0033(4) C11 0.0180(5) 0.0260(5) 0.0178(4) -0.0014(4) 0.0009(3) -0.0022(4) C12 0.0259(5) 0.0231(5) 0.0291(5) 0.0022(4) 0.0036(4) 0.0044(4) C13 0.0331(6) 0.0280(6) 0.0304(6) 0.0063(4) 0.0076(5) -0.0042(5) C14 0.0219(5) 0.0405(7) 0.0265(5) -0.0041(5) 0.0064(4) -0.0037(5) C15 0.0235(5) 0.0328(6) 0.0271(5) -0.0042(4) -0.0014(4) 0.0078(5) C16 0.0269(5) 0.0224(5) 0.0223(5) 0.0029(4) -0.0022(4) -0.0001(4) C31 0.0194(5) 0.0238(5) 0.0202(4) -0.0040(4) 0.0042(4) 0.0022(4) C32 0.0261(5) 0.0238(5) 0.0239(5) -0.0011(4) 0.0052(4) -0.0004(4) C33 0.0258(5) 0.0313(6) 0.0292(5) -0.0064(4) 0.0033(4) -0.0053(5) C34 0.0279(6) 0.0386(6) 0.0228(5) -0.0058(4) -0.0008(4) 0.0035(5) C35 0.0352(6) 0.0302(6) 0.0206(5) 0.0017(4) 0.0045(4) 0.0045(5) C36 0.0266(5) 0.0238(5) 0.0236(5) -0.0015(4) 0.0061(4) -0.0019(4) _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 O2 C2 1.2055(14) . ? C1 C11 1.5121(15) . ? C1 C2 1.5185(15) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.5175(15) . ? C3 C31 1.5072(14) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C11 C16 1.3899(15) . ? C11 C12 1.3921(15) . ? C12 C13 1.3872(16) . ? C12 H12 0.9500 . ? C13 C14 1.3839(17) . ? C13 H13 0.9500 . ? C14 C15 1.3847(17) . ? C14 H14 0.9500 . ? C15 C16 1.3883(16) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C31 C32 1.3906(15) . ? C31 C36 1.3948(15) . ? C32 C33 1.3946(16) . ? C32 H32 0.9500 . ? C33 C34 1.3847(17) . ? C33 H33 0.9500 . ? C34 C35 1.3875(18) . ? C34 H34 0.9500 . ? C35 C36 1.3880(16) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 C1 C2 113.10(8) . . ? C11 C1 H1A 109.0 . . ? C2 C1 H1A 109.0 . . ? C11 C1 H1B 109.0 . . ? C2 C1 H1B 109.0 . . ? H1A C1 H1B 107.8 . . ? O2 C2 C3 122.79(10) . . ? O2 C2 C1 120.80(10) . . ? C3 C2 C1 116.40(10) . . ? C31 C3 C2 115.57(9) . . ? C31 C3 H3A 108.4 . . ? C2 C3 H3A 108.4 . . ? C31 C3 H3B 108.4 . . ? C2 C3 H3B 108.4 . . ? H3A C3 H3B 107.4 . . ? C16 C11 C12 118.52(10) . . ? C16 C11 C1 121.18(10) . . ? C12 C11 C1 120.29(10) . . ? C13 C12 C11 120.79(10) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C14 C13 C12 120.31(11) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 119.30(10) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C14 C15 C16 120.48(10) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C11 120.60(10) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? C32 C31 C36 118.75(10) . . ? C32 C31 C3 120.85(10) . . ? C36 C31 C3 120.33(10) . . ? C31 C32 C33 120.50(10) . . ? C31 C32 H32 119.7 . . ? C33 C32 H32 119.7 . . ? C34 C33 C32 120.23(11) . . ? C34 C33 H33 119.9 . . ? C32 C33 H33 119.9 . . ? C33 C34 C35 119.63(10) . . ? C33 C34 H34 120.2 . . ? C35 C34 H34 120.2 . . ? C34 C35 C36 120.16(11) . . ? C34 C35 H35 119.9 . . ? C36 C35 H35 119.9 . . ? C35 C36 C31 120.72(10) . . ? C35 C36 H36 119.6 . . ? C31 C36 H36 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 C1 C2 O2 -121.21(13) . . . . ? C11 C1 C2 C3 59.22(14) . . . . ? O2 C2 C3 C31 14.71(16) . . . . ? C1 C2 C3 C31 -165.72(9) . . . . ? C2 C1 C11 C16 -112.61(12) . . . . ? C2 C1 C11 C12 67.65(14) . . . . ? C16 C11 C12 C13 -0.62(16) . . . . ? C1 C11 C12 C13 179.13(10) . . . . ? C11 C12 C13 C14 0.35(18) . . . . ? C12 C13 C14 C15 0.24(18) . . . . ? C13 C14 C15 C16 -0.54(17) . . . . ? C14 C15 C16 C11 0.25(16) . . . . ? C12 C11 C16 C15 0.32(15) . . . . ? C1 C11 C16 C15 -179.43(10) . . . . ? C2 C3 C31 C32 -127.42(11) . . . . ? C2 C3 C31 C36 55.66(13) . . . . ? C36 C31 C32 C33 0.30(15) . . . . ? C3 C31 C32 C33 -176.66(10) . . . . ? C31 C32 C33 C34 -0.50(17) . . . . ? C32 C33 C34 C35 0.16(17) . . . . ? C33 C34 C35 C36 0.37(17) . . . . ? C34 C35 C36 C31 -0.57(17) . . . . ? C32 C31 C36 C35 0.23(15) . . . . ? C3 C31 C36 C35 177.21(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1 H1B O2 0.99 2.47 3.2407(15) 134.8 2_646