Electronic Supplementary Material for PCPP This journal is © The Owner Communities 2005 data_global _journal_name_full Phys.Chem.Chem.Phys.(PCCP) _journal_coden_Cambridge 1326 _publ_contact_author_name 'ProfD Paulo J. A. Ribeiro-Claro' _publ_contact_author_address ; Departamento de Qu\'imica Universidade de Aveiro Campus de Santiago Aveiro P-3810-193 AVEIRO PORTUGAL ; _publ_contact_author_email PCLARO@DQ.UA.PT _publ_section_title ; C-H...O Hydrogen Bonding in 4-Phenyl-Benzaldehyde: a comprehensive crystallographic, spectroscopic and computational study ; loop_ _publ_author_name 'Paulo Ribeiro-Claro' 'Ana M. Amado' 'A.M.A.da Costa' 'M. Drew' 'Vitor Felix' ; N.Fonseca ; 'Brian J. Goodfellow' 'Mariela Nolasco' 'Pedro D. Vaz' data_compound4-phenyl-benzaldehyde _database_code_depnum_ccdc_archive 'CCDC 274570' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H20 O2' _chemical_formula_weight 364.42 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 Monoclinic _symmetry_space_group_name_H-M P21/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 13.848(16) _cell_length_b 9.052(12) _cell_length_c 17.146(21) _cell_angle_alpha 90.00 _cell_angle_beta 114.32(1) _cell_angle_gamma 90.00 _cell_volume 1959(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 50 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 26.06 _exptl_crystal_description 'irregular prism' _exptl_crystal_colour 'clear yellow' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type 'not absorption correction' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'MAR research image plate system' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6649 _diffrn_reflns_av_R_equivalents 0.1176 _diffrn_reflns_av_sigmaI/netI 0.1099 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 26.06 _reflns_number_total 3772 _reflns_number_gt 1677 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction 'W. Kabsch, J. Appl. Crystallogr. 21,916,1983' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1999)' _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 w=1/[\s^2^(Fo^2^)+(0.1558P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.029(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3772 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2263 _refine_ls_R_factor_gt 0.1055 _refine_ls_wR_factor_ref 0.3264 _refine_ls_wR_factor_gt 0.2608 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O71A O 1.2607(3) 0.8517(5) 1.1654(3) 0.1071(14) Uani 1 d . . . C7A C 1.1993(4) 0.7647(7) 1.1703(3) 0.0869(17) Uani 1 d . . . H7A H 1.2219 0.7104 1.2208 0.104 Uiso 1 calc R . . C1A C 1.0929(3) 0.7330(6) 1.1068(3) 0.0686(13) Uani 1 d . . . C2A C 1.0515(4) 0.8028(6) 1.0284(3) 0.0794(15) Uani 1 d . . . H2A H 1.0929 0.8697 1.0145 0.095 Uiso 1 calc R . . C3A C 0.9505(4) 0.7747(6) 0.9711(3) 0.0763(14) Uani 1 d . . . H3A H 0.9246 0.8231 0.9186 0.092 Uiso 1 calc R . . C4A C 0.8844(3) 0.6762(5) 0.9882(3) 0.0619(12) Uani 1 d . . . C5A C 0.9262(4) 0.6032(6) 1.0659(3) 0.0743(14) Uani 1 d . . . H5A H 0.8850 0.5352 1.0793 0.089 Uiso 1 calc R . . C6A C 1.0287(4) 0.6311(6) 1.1234(3) 0.0749(14) Uani 1 d . . . H6A H 1.0558 0.5800 1.1751 0.090 Uiso 1 calc R . . C8A C 0.7727(3) 0.6527(6) 0.9270(3) 0.0653(13) Uani 1 d . . . C9A C 0.7134(4) 0.7620(6) 0.8734(3) 0.0722(14) Uani 1 d . . . H9A H 0.7445 0.8535 0.8746 0.087 Uiso 1 calc R . . C10A C 0.6077(4) 0.7399(7) 0.8170(3) 0.0882(17) Uani 1 d . . . H10A H 0.5685 0.8172 0.7829 0.106 Uiso 1 calc R . . C11A C 0.5621(4) 0.6049(7) 0.8122(3) 0.0841(16) Uani 1 d . . . H11A H 0.4925 0.5883 0.7735 0.101 Uiso 1 calc R . . C12A C 0.6201(4) 0.4937(6) 0.8653(3) 0.0780(15) Uani 1 d . . . H12A H 0.5888 0.4020 0.8632 0.094 Uiso 1 calc R . . C13A C 0.7245(4) 0.5159(6) 0.9220(3) 0.0707(13) Uani 1 d . . . H13A H 0.7627 0.4389 0.9571 0.085 Uiso 1 calc R . . C13B C 0.8063(3) 0.9939(6) 0.5775(3) 0.0701(13) Uani 1 d . . . H13B H 0.8120 1.0704 0.5434 0.084 Uiso 1 calc R . . C12B C 0.7586(4) 1.0188(7) 0.6339(3) 0.0803(15) Uani 1 d . . . H12B H 0.7341 1.1129 0.6379 0.096 Uiso 1 calc R . . C11B C 0.7474(4) 0.9072(7) 0.6836(3) 0.0830(15) Uani 1 d . . . H11B H 0.7150 0.9252 0.7206 0.100 Uiso 1 calc R . . C10B C 0.7847(4) 0.7680(6) 0.6782(3) 0.0798(15) Uani 1 d . . . H10B H 0.7770 0.6915 0.7114 0.096 Uiso 1 calc R . . C9B C 0.8337(3) 0.7415(6) 0.6230(3) 0.0714(13) Uani 1 d . . . H9B H 0.8590 0.6474 0.6202 0.086 Uiso 1 calc R . . C8B C 0.8455(3) 0.8532(5) 0.5723(3) 0.0636(12) Uani 1 d . . . C4B C 0.8967(3) 0.8253(5) 0.5126(3) 0.0615(12) Uani 1 d . . . C3B C 0.9773(4) 0.7204(6) 0.5323(3) 0.0739(14) Uani 1 d . . . H3B H 1.0015 0.6719 0.5847 0.089 Uiso 1 calc R . . C2B C 1.0216(4) 0.6872(6) 0.4759(3) 0.0725(14) Uani 1 d . . . H2B H 1.0753 0.6171 0.4906 0.087 Uiso 1 calc R . . C1B C 0.9869(3) 0.7574(5) 0.3975(3) 0.0680(13) Uani 1 d . . . C6B C 0.9114(4) 0.8668(6) 0.3791(3) 0.0718(14) Uani 1 d . . . H6B H 0.8900 0.9183 0.3278 0.086 Uiso 1 calc R . . C5B C 0.8666(3) 0.9013(5) 0.4367(3) 0.0694(13) Uani 1 d . . . H5B H 0.8163 0.9761 0.4236 0.083 Uiso 1 calc R . . C7B C 1.0282(4) 0.7151(7) 0.3328(3) 0.0793(15) Uani 1 d . . . H7B H 1.0037 0.7683 0.2818 0.095 Uiso 1 calc R . . O71B O 1.0897(3) 0.6193(5) 0.3414(2) 0.1067(14) Uani 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 O71A 0.083(3) 0.118(3) 0.118(3) -0.036(3) 0.038(2) -0.025(3) C7A 0.075(4) 0.103(5) 0.076(4) -0.021(3) 0.024(3) -0.004(3) C1A 0.063(3) 0.076(3) 0.065(3) -0.006(3) 0.024(3) 0.000(3) C2A 0.076(3) 0.083(4) 0.074(4) 0.003(3) 0.027(3) -0.012(3) C3A 0.079(3) 0.084(4) 0.061(3) 0.008(3) 0.024(3) -0.001(3) C4A 0.060(3) 0.070(3) 0.053(3) 0.001(2) 0.020(2) 0.002(2) C5A 0.070(3) 0.077(3) 0.075(3) 0.006(3) 0.028(3) -0.001(3) C6A 0.071(3) 0.081(4) 0.064(3) 0.004(3) 0.019(3) 0.006(3) C8A 0.069(3) 0.076(3) 0.049(3) 0.000(3) 0.023(2) 0.004(3) C9A 0.072(3) 0.080(4) 0.058(3) 0.007(3) 0.020(3) -0.008(3) C10A 0.085(4) 0.104(5) 0.067(4) 0.002(3) 0.023(3) 0.008(3) C11A 0.076(4) 0.107(5) 0.059(3) -0.005(3) 0.016(3) 0.003(4) C12A 0.079(3) 0.086(4) 0.068(3) -0.015(3) 0.030(3) -0.017(3) C13A 0.074(3) 0.074(3) 0.063(3) -0.003(3) 0.027(3) -0.002(3) C13B 0.064(3) 0.074(3) 0.066(3) -0.002(3) 0.020(2) -0.004(3) C12B 0.075(3) 0.083(4) 0.071(3) -0.005(3) 0.018(3) 0.006(3) C11B 0.078(3) 0.098(4) 0.068(3) -0.008(3) 0.025(3) -0.011(3) C10B 0.096(4) 0.085(4) 0.058(3) 0.001(3) 0.030(3) -0.013(3) C9B 0.073(3) 0.069(3) 0.064(3) -0.004(3) 0.020(3) -0.002(3) C8B 0.054(3) 0.072(3) 0.053(3) 0.000(2) 0.010(2) -0.005(2) C4B 0.050(2) 0.070(3) 0.056(3) -0.003(2) 0.012(2) -0.006(2) C3B 0.070(3) 0.084(3) 0.054(3) 0.012(3) 0.012(2) 0.011(3) C2B 0.063(3) 0.087(4) 0.060(3) 0.011(3) 0.017(2) 0.015(3) C1B 0.060(3) 0.068(3) 0.070(3) 0.008(3) 0.021(2) 0.003(3) C6B 0.071(3) 0.083(4) 0.054(3) 0.019(3) 0.018(2) 0.005(3) C5B 0.058(3) 0.075(3) 0.064(3) 0.011(3) 0.014(2) 0.001(2) C7B 0.075(3) 0.105(4) 0.054(3) 0.011(3) 0.023(3) 0.013(3) O71B 0.116(3) 0.115(3) 0.097(3) 0.020(2) 0.052(3) 0.041(3) _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 O71A C7A 1.187(6) . ? C7A C1A 1.455(7) . ? C1A C2A 1.380(7) . ? C1A C6A 1.390(7) . ? C2A C3A 1.362(6) . ? C3A C4A 1.393(6) . ? C4A C5A 1.382(6) . ? C4A C8A 1.484(6) . ? C5A C6A 1.378(6) . ? C8A C9A 1.369(6) . ? C8A C13A 1.393(7) . ? C9A C10A 1.398(7) . ? C10A C11A 1.362(8) . ? C11A C12A 1.373(7) . ? C12A C13A 1.385(6) . ? C13B C12B 1.396(7) . ? C13B C8B 1.401(7) . ? C12B C11B 1.370(7) . ? C11B C10B 1.379(7) . ? C10B C9B 1.393(7) . ? C9B C8B 1.386(6) . ? C8B C4B 1.488(6) . ? C4B C5B 1.376(6) . ? C4B C3B 1.396(6) . ? C3B C2B 1.376(6) . ? C2B C1B 1.381(6) . ? C1B C6B 1.379(6) . ? C1B C7B 1.493(7) . ? C6B C5B 1.400(6) . ? C7B O71B 1.182(6) . ? 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 O71A C7A C1A 127.7(6) . . ? C2A C1A C6A 117.4(4) . . ? C2A C1A C7A 121.7(5) . . ? C6A C1A C7A 120.9(5) . . ? C3A C2A C1A 120.6(5) . . ? C2A C3A C4A 122.4(5) . . ? C5A C4A C3A 117.3(4) . . ? C5A C4A C8A 120.9(4) . . ? C3A C4A C8A 121.8(4) . . ? C6A C5A C4A 120.1(5) . . ? C5A C6A C1A 122.1(5) . . ? C9A C8A C13A 117.5(4) . . ? C9A C8A C4A 122.2(5) . . ? C13A C8A C4A 120.3(4) . . ? C8A C9A C10A 121.9(5) . . ? C11A C10A C9A 119.8(5) . . ? C10A C11A C12A 119.2(5) . . ? C11A C12A C13A 121.0(5) . . ? C12A C13A C8A 120.5(5) . . ? C12B C13B C8B 119.7(5) . . ? C11B C12B C13B 121.3(5) . . ? C12B C11B C10B 119.3(5) . . ? C11B C10B C9B 120.2(5) . . ? C8B C9B C10B 121.1(5) . . ? C9B C8B C13B 118.4(4) . . ? C9B C8B C4B 121.4(4) . . ? C13B C8B C4B 120.3(4) . . ? C5B C4B C3B 118.0(4) . . ? C5B C4B C8B 121.4(4) . . ? C3B C4B C8B 120.6(4) . . ? C2B C3B C4B 121.4(4) . . ? C3B C2B C1B 120.4(5) . . ? C6B C1B C2B 118.7(4) . . ? C6B C1B C7B 120.0(4) . . ? C2B C1B C7B 121.3(5) . . ? C1B C6B C5B 120.9(4) . . ? C4B C5B C6B 120.4(5) . . ? O71B C7B C1B 124.9(5) . . ? _diffrn_measured_fraction_theta_max 0.915 _diffrn_reflns_theta_full 26.06 _diffrn_measured_fraction_theta_full 0.915 _refine_diff_density_max 0.253 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.056