# 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