# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2009 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Hiroyuki Takemura' _publ_contact_author_email TAKEMURAH@FC.JWU.AC.JP _publ_section_title ; Intramolecular CF...HO hydrogen bond of 2-fluorophenyldiphenylmethanol ; loop_ _publ_author_name 'Hiroyuki Takemura' 'Tetsuo Iwanaga' 'Megumi Kaneko' 'Katsuya Sako' # Attachment 'H Takemura_cif.txt' data_tri _database_code_depnum_ccdc_archive 'CCDC 693164' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H15 F O ' _chemical_formula_sum 'C19 H15 F O' _chemical_formula_weight 278.31 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' F F 0.0171 0.0103 '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 1 21/n 1' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.2379(3) _cell_length_b 10.9417(4) _cell_length_c 15.6797(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.2076(8) _cell_angle_gamma 90.00 _cell_volume 1411.10(8) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 16207 _cell_measurement_theta_min 1.3 _cell_measurement_theta_max 27.3 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.37 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9546 _exptl_absorpt_correction_T_max 0.9680 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3160 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 27.27 _reflns_number_total 3160 _reflns_number_gt 2749 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3160 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0614 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1831 _refine_ls_wR_factor_gt 0.1797 _refine_ls_goodness_of_fit_ref 1.409 _refine_ls_restrained_S_all 1.409 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.86656(18) 0.24060(13) 0.53655(9) 0.0176(3) Uani 1 1 d . . . C2 C 0.77975(18) 0.30761(14) 0.46095(10) 0.0197(3) Uani 1 1 d . . . C3 C 0.70949(19) 0.42312(15) 0.46750(10) 0.0220(4) Uani 1 1 d . . . H1 H 0.7164 0.4641 0.5210 0.026 Uiso 1 1 calc R . . C4 C 0.6295(2) 0.47978(15) 0.39754(11) 0.0261(4) Uani 1 1 d . . . H2 H 0.5839 0.5588 0.4036 0.031 Uiso 1 1 calc R . . C5 C 0.6164(2) 0.42136(17) 0.31923(11) 0.0289(4) Uani 1 1 d . . . H3 H 0.5612 0.4600 0.2717 0.035 Uiso 1 1 calc R . . C6 C 0.6842(2) 0.30559(17) 0.31017(11) 0.0287(4) Uani 1 1 d . . . H4 H 0.6756 0.2641 0.2569 0.034 Uiso 1 1 calc R . . C7 C 0.7639(2) 0.25291(15) 0.38054(10) 0.0229(4) Uani 1 1 d . . . C8 C 1.04709(19) 0.21910(14) 0.52329(10) 0.0188(3) Uani 1 1 d . . . C9 C 1.1311(2) 0.28114(15) 0.46175(10) 0.0235(4) Uani 1 1 d . . . H5 H 1.0757 0.3389 0.4255 0.028 Uiso 1 1 calc R . . C10 C 1.2962(2) 0.25856(17) 0.45331(12) 0.0295(4) Uani 1 1 d . . . H6 H 1.3520 0.2999 0.4105 0.035 Uiso 1 1 calc R . . C11 C 1.3789(2) 0.17693(16) 0.50649(12) 0.0300(4) Uani 1 1 d . . . H7 H 1.4914 0.1624 0.5005 0.036 Uiso 1 1 calc R . . C12 C 1.2969(2) 0.11550(16) 0.56929(12) 0.0288(4) Uani 1 1 d . . . H8 H 1.3535 0.0596 0.6066 0.035 Uiso 1 1 calc R . . C13 C 1.1322(2) 0.13666(15) 0.57682(10) 0.0237(4) Uani 1 1 d . . . H9 H 1.0764 0.0942 0.6192 0.028 Uiso 1 1 calc R . . C14 C 0.84738(19) 0.31012(13) 0.62009(9) 0.0192(3) Uani 1 1 d . . . C15 C 0.9552(2) 0.40321(15) 0.64544(10) 0.0241(4) Uani 1 1 d . . . H10 H 1.0443 0.4215 0.6117 0.029 Uiso 1 1 calc R . . C16 C 0.9335(2) 0.46984(16) 0.71986(11) 0.0300(4) Uani 1 1 d . . . H11 H 1.0070 0.5337 0.7362 0.036 Uiso 1 1 calc R . . C17 C 0.8049(2) 0.44293(17) 0.76999(11) 0.0317(4) Uani 1 1 d . . . H12 H 0.7898 0.4880 0.8207 0.038 Uiso 1 1 calc R . . C18 C 0.6988(2) 0.34984(17) 0.74545(11) 0.0303(4) Uani 1 1 d . . . H13 H 0.6113 0.3305 0.7801 0.036 Uiso 1 1 calc R . . C19 C 0.7183(2) 0.28426(16) 0.67093(10) 0.0244(4) Uani 1 1 d . . . H14 H 0.6433 0.2215 0.6545 0.029 Uiso 1 1 calc R . . F1 F 0.83271(15) 0.14137(9) 0.36998(7) 0.0352(3) Uani 1 1 d . . . O1 O 0.78794(14) 0.12392(10) 0.54718(7) 0.0221(3) Uani 1 1 d . . . H15 H 0.814(5) 0.068(3) 0.502(2) 0.098(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0181(7) 0.0164(7) 0.0187(8) 0.0004(5) 0.0044(6) -0.0012(5) C2 0.0180(7) 0.0206(8) 0.0207(8) 0.0011(6) 0.0030(6) -0.0025(6) C3 0.0210(7) 0.0217(8) 0.0233(8) -0.0002(6) 0.0029(6) 0.0000(6) C4 0.0247(8) 0.0242(8) 0.0294(9) 0.0034(7) 0.0020(7) 0.0037(6) C5 0.0306(9) 0.0323(9) 0.0236(8) 0.0056(7) -0.0006(6) 0.0029(7) C6 0.0342(9) 0.0322(9) 0.0195(8) -0.0012(7) -0.0003(7) -0.0019(7) C7 0.0251(8) 0.0217(8) 0.0223(8) 0.0004(6) 0.0040(6) 0.0011(6) C8 0.0186(7) 0.0180(7) 0.0199(8) -0.0044(6) 0.0030(6) -0.0017(6) C9 0.0234(8) 0.0226(8) 0.0252(8) 0.0000(6) 0.0057(6) -0.0027(6) C10 0.0251(9) 0.0306(9) 0.0339(10) -0.0079(7) 0.0105(7) -0.0077(7) C11 0.0180(8) 0.0319(9) 0.0401(10) -0.0126(8) 0.0020(7) -0.0009(7) C12 0.0242(8) 0.0268(9) 0.0346(9) -0.0057(7) -0.0045(7) 0.0029(7) C13 0.0245(8) 0.0240(8) 0.0227(8) -0.0018(6) 0.0015(6) 0.0003(6) C14 0.0234(8) 0.0175(7) 0.0168(7) 0.0024(6) 0.0016(6) 0.0035(6) C15 0.0286(8) 0.0227(8) 0.0211(8) -0.0022(6) 0.0033(6) -0.0018(6) C16 0.0412(10) 0.0244(8) 0.0244(9) -0.0047(7) 0.0015(7) -0.0017(7) C17 0.0468(11) 0.0292(9) 0.0194(8) -0.0032(7) 0.0053(7) 0.0087(8) C18 0.0356(10) 0.0340(10) 0.0225(8) 0.0035(7) 0.0117(7) 0.0063(7) C19 0.0253(8) 0.0254(8) 0.0230(8) 0.0017(6) 0.0056(6) 0.0020(6) F1 0.0458(7) 0.0298(6) 0.0300(6) -0.0038(4) 0.0024(5) 0.0065(5) O1 0.0230(6) 0.0169(6) 0.0268(6) 0.0000(5) 0.0057(4) -0.0037(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 C1 O1 1.4455(18) . ? C1 C14 1.531(2) . ? C1 C8 1.531(2) . ? C1 C2 1.536(2) . ? C2 C7 1.395(2) . ? C2 C3 1.396(2) . ? C3 C4 1.393(2) . ? C3 H1 0.9500 . ? C4 C5 1.383(2) . ? C4 H2 0.9500 . ? C5 C6 1.395(3) . ? C5 H3 0.9500 . ? C6 C7 1.378(2) . ? C6 H4 0.9500 . ? C7 F1 1.3597(18) . ? C8 C13 1.394(2) . ? C8 C9 1.395(2) . ? C9 C10 1.396(2) . ? C9 H5 0.9500 . ? C10 C11 1.376(3) . ? C10 H6 0.9500 . ? C11 C12 1.397(3) . ? C11 H7 0.9500 . ? C12 C13 1.388(2) . ? C12 H8 0.9500 . ? C13 H9 0.9500 . ? C14 C19 1.393(2) . ? C14 C15 1.394(2) . ? C15 C16 1.396(2) . ? C15 H10 0.9500 . ? C16 C17 1.386(3) . ? C16 H11 0.9500 . ? C17 C18 1.383(3) . ? C17 H12 0.9500 . ? C18 C19 1.388(2) . ? C18 H13 0.9500 . ? C19 H14 0.9500 . ? O1 H15 0.97(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C14 105.78(11) . . ? O1 C1 C8 108.95(12) . . ? C14 C1 C8 109.88(12) . . ? O1 C1 C2 108.57(12) . . ? C14 C1 C2 110.93(12) . . ? C8 C1 C2 112.48(12) . . ? C7 C2 C3 115.88(14) . . ? C7 C2 C1 120.57(14) . . ? C3 C2 C1 123.53(14) . . ? C4 C3 C2 121.64(15) . . ? C4 C3 H1 119.2 . . ? C2 C3 H1 119.2 . . ? C5 C4 C3 120.24(15) . . ? C5 C4 H2 119.9 . . ? C3 C4 H2 119.9 . . ? C4 C5 C6 119.88(16) . . ? C4 C5 H3 120.1 . . ? C6 C5 H3 120.1 . . ? C7 C6 C5 118.28(15) . . ? C7 C6 H4 120.9 . . ? C5 C6 H4 120.9 . . ? F1 C7 C6 117.46(15) . . ? F1 C7 C2 118.46(14) . . ? C6 C7 C2 124.08(15) . . ? C13 C8 C9 118.65(15) . . ? C13 C8 C1 118.49(13) . . ? C9 C8 C1 122.84(14) . . ? C8 C9 C10 120.21(16) . . ? C8 C9 H5 119.9 . . ? C10 C9 H5 119.9 . . ? C11 C10 C9 120.61(16) . . ? C11 C10 H6 119.7 . . ? C9 C10 H6 119.7 . . ? C10 C11 C12 119.80(16) . . ? C10 C11 H7 120.1 . . ? C12 C11 H7 120.1 . . ? C13 C12 C11 119.55(17) . . ? C13 C12 H8 120.2 . . ? C11 C12 H8 120.2 . . ? C12 C13 C8 121.17(16) . . ? C12 C13 H9 119.4 . . ? C8 C13 H9 119.4 . . ? C19 C14 C15 118.65(15) . . ? C19 C14 C1 120.49(14) . . ? C15 C14 C1 120.82(14) . . ? C14 C15 C16 120.71(16) . . ? C14 C15 H10 119.6 . . ? C16 C15 H10 119.6 . . ? C17 C16 C15 120.05(16) . . ? C17 C16 H11 120.0 . . ? C15 C16 H11 120.0 . . ? C18 C17 C16 119.36(16) . . ? C18 C17 H12 120.3 . . ? C16 C17 H12 120.3 . . ? C17 C18 C19 120.92(16) . . ? C17 C18 H13 119.5 . . ? C19 C18 H13 119.5 . . ? C18 C19 C14 120.31(16) . . ? C18 C19 H14 119.8 . . ? C14 C19 H14 119.8 . . ? C1 O1 H15 111(2) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.27 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.054 _refine_diff_density_min -0.530 _refine_diff_density_rms 0.061