# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Alison Stuart' _publ_contact_author_email alison.stuart@le.ac.uk loop_ _publ_author_name A.Stuart M.Fornalczyk K.Singh data_10097 _database_code_depnum_ccdc_archive 'CCDC 859759' #TrackingRef '- MF10097.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 F N O2' _chemical_formula_sum 'C18 H20 F N O2' _chemical_formula_weight 301.35 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 0.0000 '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' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 19.119(6) _cell_length_b 5.5114(16) _cell_length_c 15.207(4) _cell_angle_alpha 90.00 _cell_angle_beta 109.351(6) _cell_angle_gamma 90.00 _cell_volume 1511.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 337 _cell_measurement_theta_min 2.234 _cell_measurement_theta_max 24.306 _exptl_crystal_description plate _exptl_crystal_colour colourless _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 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.412 _exptl_absorpt_correction_T_max 0.969 _exptl_absorpt_process_details ; absorption correction based on 1017 reflections(SADABS);Rint 0.0890 before correction and 0.0545 after. ; _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 Apex 2000 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5986 _diffrn_reflns_av_R_equivalents 0.1603 _diffrn_reflns_av_sigmaI/netI 0.1853 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1648 _reflns_number_gt 856 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0172P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration ,rm _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1648 _refine_ls_number_parameters 203 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1326 _refine_ls_R_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.0972 _refine_ls_wR_factor_gt 0.0819 _refine_ls_goodness_of_fit_ref 0.826 _refine_ls_restrained_S_all 0.826 _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 F1 F 0.55368(16) 0.3573(6) 0.60584(19) 0.0398(9) Uani 1 1 d . . . O1 O 0.6580(2) 0.9134(6) 0.6683(2) 0.0370(10) Uani 1 1 d . . . H1 H 0.6405 0.9374 0.7115 0.056 Uiso 1 1 calc R . . O2 O 0.56283(19) 0.8314(6) 0.7647(2) 0.0382(11) Uani 1 1 d . . . N1 N 0.5364(2) 0.4314(8) 0.7668(3) 0.0335(12) Uani 1 1 d . . . H1A H 0.5346 0.2890 0.7399 0.040 Uiso 1 1 calc R . . C1 C 0.6445(3) 0.6657(10) 0.6370(4) 0.0303(15) Uani 1 1 d . . . C2 C 0.5673(3) 0.5958(10) 0.6363(4) 0.0311(15) Uani 1 1 d . . . H2 H 0.5307 0.7017 0.5899 0.037 Uiso 1 1 calc R . . C3 C 0.5558(3) 0.6267(12) 0.7276(4) 0.0310(15) Uani 1 1 d . . . C4 C 0.5181(3) 0.4472(10) 0.8527(3) 0.0305(14) Uani 1 1 d . . . H4 H 0.4891 0.5997 0.8499 0.037 Uiso 1 1 calc R . . C5 C 0.4680(3) 0.2346(10) 0.8544(4) 0.0383(16) Uani 1 1 d . . . H5A H 0.4249 0.2347 0.7971 0.058 Uiso 1 1 calc R . . H5B H 0.4512 0.2497 0.9085 0.058 Uiso 1 1 calc R . . H5C H 0.4954 0.0825 0.8588 0.058 Uiso 1 1 calc R . . C6 C 0.6472(3) 0.6646(11) 0.5384(4) 0.0279(14) Uani 1 1 d . . . C7 C 0.6148(3) 0.8583(10) 0.4797(3) 0.0329(15) Uani 1 1 d . . . H7 H 0.5936 0.9896 0.5026 0.039 Uiso 1 1 calc R . . C8 C 0.6136(3) 0.8590(12) 0.3876(4) 0.0431(16) Uani 1 1 d . . . H8 H 0.5919 0.9926 0.3486 0.052 Uiso 1 1 calc R . . C9 C 0.6427(3) 0.6734(13) 0.3524(4) 0.0439(17) Uani 1 1 d . . . H9 H 0.6411 0.6754 0.2893 0.053 Uiso 1 1 calc R . . C10 C 0.6746(3) 0.4812(12) 0.4104(4) 0.0474(18) Uani 1 1 d . . . H10 H 0.6958 0.3509 0.3868 0.057 Uiso 1 1 calc R . . C11 C 0.6763(3) 0.4758(12) 0.5016(4) 0.0378(16) Uani 1 1 d . . . H11 H 0.6977 0.3405 0.5398 0.045 Uiso 1 1 calc R . . C12 C 0.7034(3) 0.5063(9) 0.7037(3) 0.0302(15) Uani 1 1 d . . . H12A H 0.7527 0.5678 0.7088 0.045 Uiso 1 1 calc R . . H12B H 0.6981 0.3395 0.6801 0.045 Uiso 1 1 calc R . . H12C H 0.6974 0.5090 0.7653 0.045 Uiso 1 1 calc R . . C13 C 0.5861(3) 0.4596(11) 0.9390(4) 0.0282(14) Uani 1 1 d . . . C14 C 0.5960(3) 0.6503(11) 1.0005(4) 0.0306(14) Uani 1 1 d . . . H14 H 0.5608 0.7785 0.9870 0.037 Uiso 1 1 calc R . . C15 C 0.6554(3) 0.6579(11) 1.0800(4) 0.0361(15) Uani 1 1 d . . . H15 H 0.6606 0.7917 1.1211 0.043 Uiso 1 1 calc R . . C16 C 0.7072(3) 0.4817(12) 1.1026(4) 0.0420(16) Uani 1 1 d . . . H16 H 0.7478 0.4886 1.1593 0.050 Uiso 1 1 calc R . . C17 C 0.6995(3) 0.2881(11) 1.0404(4) 0.0405(16) Uani 1 1 d . . . H17 H 0.7359 0.1635 1.0537 0.049 Uiso 1 1 calc R . . C18 C 0.6385(3) 0.2788(10) 0.9590(4) 0.0325(15) Uani 1 1 d . . . H18 H 0.6330 0.1466 0.9172 0.039 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 F1 0.055(2) 0.038(2) 0.0332(19) -0.0111(18) 0.0238(17) -0.0137(17) O1 0.050(3) 0.031(3) 0.029(2) -0.003(2) 0.0120(19) -0.001(2) O2 0.054(3) 0.031(3) 0.034(2) 0.003(2) 0.019(2) 0.007(2) N1 0.044(3) 0.026(3) 0.034(3) -0.008(3) 0.018(2) 0.004(3) C1 0.032(4) 0.023(3) 0.034(4) -0.007(3) 0.008(3) 0.001(3) C2 0.038(4) 0.028(4) 0.026(3) -0.006(3) 0.009(3) 0.005(3) C3 0.028(4) 0.036(4) 0.029(3) 0.001(4) 0.008(3) 0.009(3) C4 0.038(4) 0.029(4) 0.030(3) -0.005(3) 0.019(3) 0.000(3) C5 0.042(4) 0.038(4) 0.038(4) -0.002(3) 0.017(3) -0.002(3) C6 0.028(3) 0.030(4) 0.025(3) 0.001(3) 0.008(3) -0.003(3) C7 0.034(3) 0.035(4) 0.031(3) -0.002(3) 0.014(3) -0.011(3) C8 0.046(4) 0.042(4) 0.039(4) 0.014(4) 0.011(3) -0.011(4) C9 0.049(4) 0.055(5) 0.028(4) 0.005(4) 0.012(3) -0.018(4) C10 0.037(4) 0.059(5) 0.048(4) -0.027(4) 0.017(3) -0.012(4) C11 0.034(4) 0.041(4) 0.038(4) -0.003(3) 0.011(3) 0.000(3) C12 0.027(3) 0.031(4) 0.028(3) -0.001(3) 0.002(3) 0.001(3) C13 0.029(3) 0.030(3) 0.029(3) 0.008(3) 0.015(3) 0.005(3) C14 0.033(4) 0.033(4) 0.029(3) 0.002(3) 0.013(3) 0.002(3) C15 0.042(4) 0.023(3) 0.043(4) 0.000(3) 0.014(3) -0.005(3) C16 0.041(4) 0.047(4) 0.036(4) 0.008(4) 0.011(3) -0.009(4) C17 0.038(4) 0.037(4) 0.047(4) 0.011(4) 0.015(3) 0.010(3) C18 0.035(4) 0.036(4) 0.032(4) 0.000(3) 0.018(3) -0.005(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 F1 C2 1.389(6) . ? O1 C1 1.441(6) . ? O1 H1 0.8400 . ? O2 C3 1.249(6) . ? N1 C3 1.341(7) . ? N1 C4 1.463(6) . ? N1 H1A 0.8800 . ? C1 C6 1.516(7) . ? C1 C12 1.521(6) . ? C1 C2 1.523(7) . ? C2 C3 1.485(7) . ? C2 H2 1.0000 . ? C4 C13 1.511(7) . ? C4 C5 1.520(7) . ? C4 H4 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C11 1.383(7) . ? C6 C7 1.398(7) . ? C7 C8 1.393(7) . ? C7 H7 0.9500 . ? C8 C9 1.357(8) . ? C8 H8 0.9500 . ? C9 C10 1.384(8) . ? C9 H9 0.9500 . ? C10 C11 1.378(7) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C18 1.374(7) . ? C13 C14 1.378(7) . ? C14 C15 1.358(7) . ? C14 H14 0.9500 . ? C15 C16 1.347(8) . ? C15 H15 0.9500 . ? C16 C17 1.401(8) . ? C16 H16 0.9500 . ? C17 C18 1.393(7) . ? C17 H17 0.9500 . ? C18 H18 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 C1 O1 H1 109.5 . . ? C3 N1 C4 122.2(5) . . ? C3 N1 H1A 118.9 . . ? C4 N1 H1A 118.9 . . ? O1 C1 C6 105.7(5) . . ? O1 C1 C12 108.3(4) . . ? C6 C1 C12 113.4(5) . . ? O1 C1 C2 108.0(4) . . ? C6 C1 C2 110.0(4) . . ? C12 C1 C2 111.1(4) . . ? F1 C2 C3 110.5(5) . . ? F1 C2 C1 108.4(4) . . ? C3 C2 C1 114.0(4) . . ? F1 C2 H2 107.9 . . ? C3 C2 H2 107.9 . . ? C1 C2 H2 107.9 . . ? O2 C3 N1 121.9(5) . . ? O2 C3 C2 120.0(6) . . ? N1 C3 C2 118.1(6) . . ? N1 C4 C13 112.8(4) . . ? N1 C4 C5 108.0(4) . . ? C13 C4 C5 112.7(5) . . ? N1 C4 H4 107.7 . . ? C13 C4 H4 107.7 . . ? C5 C4 H4 107.7 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C11 C6 C7 117.9(5) . . ? C11 C6 C1 123.6(5) . . ? C7 C6 C1 118.4(5) . . ? C8 C7 C6 120.0(6) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C9 C8 C7 121.5(6) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? C8 C9 C10 118.5(6) . . ? C8 C9 H9 120.7 . . ? C10 C9 H9 120.7 . . ? C11 C10 C9 121.1(6) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C6 120.9(6) . . ? C10 C11 H11 119.6 . . ? C6 C11 H11 119.6 . . ? C1 C12 H12A 109.5 . . ? C1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C18 C13 C14 118.4(5) . . ? C18 C13 C4 120.9(5) . . ? C14 C13 C4 120.6(5) . . ? C15 C14 C13 121.0(6) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C16 C15 C14 122.1(6) . . ? C16 C15 H15 118.9 . . ? C14 C15 H15 118.9 . . ? C15 C16 C17 118.2(6) . . ? C15 C16 H16 120.9 . . ? C17 C16 H16 120.9 . . ? C18 C17 C16 119.8(6) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C13 C18 C17 120.4(6) . . ? C13 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? 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 O1 C1 C2 F1 179.8(4) . . . . ? C6 C1 C2 F1 65.0(6) . . . . ? C12 C1 C2 F1 -61.5(5) . . . . ? O1 C1 C2 C3 -56.6(6) . . . . ? C6 C1 C2 C3 -171.5(5) . . . . ? C12 C1 C2 C3 62.1(6) . . . . ? C4 N1 C3 O2 3.5(8) . . . . ? C4 N1 C3 C2 -175.0(5) . . . . ? F1 C2 C3 O2 -177.4(5) . . . . ? C1 C2 C3 O2 60.2(7) . . . . ? F1 C2 C3 N1 1.1(7) . . . . ? C1 C2 C3 N1 -121.3(5) . . . . ? C3 N1 C4 C13 -79.6(6) . . . . ? C3 N1 C4 C5 155.3(5) . . . . ? O1 C1 C6 C11 143.6(5) . . . . ? C12 C1 C6 C11 25.1(8) . . . . ? C2 C1 C6 C11 -100.1(6) . . . . ? O1 C1 C6 C7 -40.2(6) . . . . ? C12 C1 C6 C7 -158.6(4) . . . . ? C2 C1 C6 C7 76.2(6) . . . . ? C11 C6 C7 C8 -1.0(8) . . . . ? C1 C6 C7 C8 -177.5(5) . . . . ? C6 C7 C8 C9 0.7(8) . . . . ? C7 C8 C9 C10 -0.5(8) . . . . ? C8 C9 C10 C11 0.8(9) . . . . ? C9 C10 C11 C6 -1.2(8) . . . . ? C7 C6 C11 C10 1.2(8) . . . . ? C1 C6 C11 C10 177.5(5) . . . . ? N1 C4 C13 C18 -58.3(7) . . . . ? C5 C4 C13 C18 64.3(6) . . . . ? N1 C4 C13 C14 123.2(5) . . . . ? C5 C4 C13 C14 -114.2(6) . . . . ? C18 C13 C14 C15 -1.2(8) . . . . ? C4 C13 C14 C15 177.3(5) . . . . ? C13 C14 C15 C16 0.2(9) . . . . ? C14 C15 C16 C17 1.3(9) . . . . ? C15 C16 C17 C18 -1.7(9) . . . . ? C14 C13 C18 C17 0.8(8) . . . . ? C4 C13 C18 C17 -177.7(5) . . . . ? C16 C17 C18 C13 0.7(8) . . . . ? 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 O1 H1 O2 0.84 2.00 2.727(5) 144.3 . N1 H1A O2 0.88 2.58 3.347(6) 146.0 1_545 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.215 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.054 # Attachment '- MF11009.cif' data_11009 _database_code_depnum_ccdc_archive 'CCDC 859764' #TrackingRef '- MF11009.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 F N O2' _chemical_formula_sum 'C18 H20 F N O2' _chemical_formula_weight 301.35 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 0.0000 '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' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.306(3) _cell_length_b 9.746(3) _cell_length_c 18.935(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1532.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 685 _cell_measurement_theta_min 2.351 _cell_measurement_theta_max 20.337 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.795 _exptl_absorpt_correction_T_max 0.969 _exptl_absorpt_process_details ; absorption correction based on 4760 reflections(SADABS);Rint 0.0806 before correction and 0.0454 after. ; _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 Apex 2000 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11981 _diffrn_reflns_av_R_equivalents 0.0879 _diffrn_reflns_av_sigmaI/netI 0.0558 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1750 _reflns_number_gt 1506 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0374P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration ,syn _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1750 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.0801 _refine_ls_wR_factor_gt 0.0774 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _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 F1 F 0.53255(17) 0.73300(13) 0.13805(7) 0.0299(3) Uani 1 1 d . . . O1 O 0.3325(2) 1.03135(17) 0.06716(8) 0.0309(4) Uani 1 1 d . . . H1 H 0.3505 1.0787 0.1034 0.046 Uiso 1 1 calc R . . O2 O 0.4532(2) 1.06202(16) 0.20609(9) 0.0328(4) Uani 1 1 d . . . N1 N 0.4660(2) 0.85225(19) 0.25804(9) 0.0240(5) Uani 1 1 d . . . H1A H 0.4920 0.7656 0.2518 0.029 Uiso 1 1 calc R . . C1 C 0.3452(3) 0.8900(2) 0.08425(12) 0.0245(5) Uani 1 1 d . . . C2 C 0.4973(3) 0.8719(2) 0.13083(12) 0.0247(6) Uani 1 1 d . . . H2 H 0.5901 0.9183 0.1071 0.030 Uiso 1 1 calc R . . C3 C 0.4726(3) 0.9362(2) 0.20285(12) 0.0233(5) Uani 1 1 d . . . C4 C 0.4177(3) 0.8967(2) 0.32856(12) 0.0253(6) Uani 1 1 d . . . H4 H 0.3859 0.9955 0.3255 0.030 Uiso 1 1 calc R . . C5 C 0.2691(3) 0.8148(3) 0.35030(14) 0.0382(7) Uani 1 1 d . . . H5A H 0.1820 0.8315 0.3165 0.057 Uiso 1 1 calc R . . H5B H 0.2346 0.8435 0.3975 0.057 Uiso 1 1 calc R . . H5C H 0.2953 0.7167 0.3509 0.057 Uiso 1 1 calc R . . C6 C 0.1955(3) 0.8378(2) 0.12308(11) 0.0217(5) Uani 1 1 d . . . C7 C 0.0804(3) 0.9278(3) 0.14946(13) 0.0292(6) Uani 1 1 d . . . H7 H 0.0948 1.0238 0.1436 0.035 Uiso 1 1 calc R . . C8 C -0.0544(3) 0.8798(3) 0.18407(13) 0.0356(6) Uani 1 1 d . . . H8 H -0.1321 0.9427 0.2015 0.043 Uiso 1 1 calc R . . C9 C -0.0766(3) 0.7410(3) 0.19342(13) 0.0345(7) Uani 1 1 d . . . H9 H -0.1701 0.7079 0.2168 0.041 Uiso 1 1 calc R . . C10 C 0.0371(3) 0.6508(3) 0.16872(12) 0.0317(6) Uani 1 1 d . . . H10 H 0.0228 0.5550 0.1756 0.038 Uiso 1 1 calc R . . C11 C 0.1721(3) 0.6983(3) 0.13392(12) 0.0266(6) Uani 1 1 d . . . H11 H 0.2499 0.6347 0.1172 0.032 Uiso 1 1 calc R . . C12 C 0.3696(3) 0.8163(3) 0.01367(12) 0.0318(6) Uani 1 1 d . . . H12A H 0.2761 0.8325 -0.0168 0.048 Uiso 1 1 calc R . . H12B H 0.3816 0.7176 0.0220 0.048 Uiso 1 1 calc R . . H12C H 0.4667 0.8517 -0.0094 0.048 Uiso 1 1 calc R . . C13 C 0.5540(3) 0.8853(2) 0.38169(11) 0.0221(5) Uani 1 1 d . . . C14 C 0.5282(3) 0.9231(2) 0.45172(12) 0.0284(6) Uani 1 1 d . . . H14 H 0.4246 0.9537 0.4660 0.034 Uiso 1 1 calc R . . C15 C 0.6514(3) 0.9167(3) 0.50056(13) 0.0328(6) Uani 1 1 d . . . H15 H 0.6316 0.9427 0.5481 0.039 Uiso 1 1 calc R . . C16 C 0.8026(3) 0.8729(3) 0.48117(13) 0.0313(6) Uani 1 1 d . . . H16 H 0.8874 0.8693 0.5148 0.038 Uiso 1 1 calc R . . C17 C 0.8291(3) 0.8344(3) 0.41227(13) 0.0291(6) Uani 1 1 d . . . H17 H 0.9325 0.8024 0.3985 0.035 Uiso 1 1 calc R . . C18 C 0.7070(3) 0.8416(3) 0.36276(12) 0.0245(5) Uani 1 1 d . . . H18 H 0.7282 0.8164 0.3152 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 F1 0.0325(8) 0.0258(8) 0.0314(7) -0.0007(6) -0.0012(6) 0.0072(7) O1 0.0444(11) 0.0240(10) 0.0243(9) 0.0038(7) -0.0006(9) 0.0024(9) O2 0.0472(11) 0.0202(9) 0.0308(9) 0.0008(7) -0.0055(9) -0.0026(9) N1 0.0303(12) 0.0192(10) 0.0224(10) 0.0013(8) -0.0021(9) 0.0042(10) C1 0.0297(13) 0.0208(13) 0.0231(12) 0.0002(10) -0.0020(11) 0.0020(11) C2 0.0270(13) 0.0203(13) 0.0267(13) 0.0024(10) 0.0014(10) -0.0007(10) C3 0.0208(12) 0.0222(13) 0.0271(13) 0.0007(10) -0.0035(11) -0.0038(10) C4 0.0287(13) 0.0224(13) 0.0247(12) 0.0006(10) 0.0005(10) 0.0037(11) C5 0.0257(14) 0.054(2) 0.0348(15) 0.0068(13) -0.0006(12) -0.0033(13) C6 0.0236(12) 0.0252(14) 0.0163(11) -0.0018(10) -0.0055(9) 0.0010(11) C7 0.0309(14) 0.0275(14) 0.0294(14) -0.0009(11) -0.0030(11) 0.0037(11) C8 0.0290(14) 0.0427(17) 0.0351(15) -0.0102(13) 0.0008(12) 0.0081(13) C9 0.0240(13) 0.0515(18) 0.0281(14) -0.0071(13) 0.0038(11) -0.0085(13) C10 0.0343(14) 0.0320(14) 0.0290(13) -0.0006(11) 0.0004(12) -0.0056(13) C11 0.0266(13) 0.0273(14) 0.0260(13) -0.0044(11) -0.0001(11) 0.0021(11) C12 0.0376(15) 0.0344(16) 0.0236(13) -0.0010(11) 0.0026(12) 0.0006(12) C13 0.0252(12) 0.0167(12) 0.0242(12) 0.0021(9) 0.0021(10) -0.0022(11) C14 0.0275(13) 0.0283(14) 0.0294(14) 0.0004(11) 0.0063(11) 0.0044(11) C15 0.0406(15) 0.0330(16) 0.0248(13) -0.0014(11) 0.0015(12) -0.0005(13) C16 0.0331(15) 0.0293(15) 0.0314(14) 0.0034(12) -0.0103(12) -0.0040(12) C17 0.0185(12) 0.0285(15) 0.0402(15) -0.0003(12) 0.0007(11) -0.0005(11) C18 0.0277(13) 0.0216(13) 0.0240(12) -0.0018(10) 0.0047(10) -0.0015(11) _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 F1 C2 1.392(2) . ? O1 C1 1.419(3) . ? O1 H1 0.8400 . ? O2 C3 1.238(3) . ? N1 C3 1.329(3) . ? N1 C4 1.460(3) . ? N1 H1A 0.8800 . ? C1 C12 1.531(3) . ? C1 C6 1.531(3) . ? C1 C2 1.551(3) . ? C2 C3 1.515(3) . ? C2 H2 1.0000 . ? C4 C13 1.519(3) . ? C4 C5 1.527(3) . ? C4 H4 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C11 1.389(3) . ? C6 C7 1.390(3) . ? C7 C8 1.379(4) . ? C7 H7 0.9500 . ? C8 C9 1.377(4) . ? C8 H8 0.9500 . ? C9 C10 1.372(4) . ? C9 H9 0.9500 . ? C10 C11 1.380(3) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C18 1.387(3) . ? C13 C14 1.393(3) . ? C14 C15 1.381(4) . ? C14 H14 0.9500 . ? C15 C16 1.377(4) . ? C15 H15 0.9500 . ? C16 C17 1.375(3) . ? C16 H16 0.9500 . ? C17 C18 1.382(3) . ? C17 H17 0.9500 . ? C18 H18 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 C1 O1 H1 109.5 . . ? C3 N1 C4 123.2(2) . . ? C3 N1 H1A 118.4 . . ? C4 N1 H1A 118.4 . . ? O1 C1 C12 105.43(19) . . ? O1 C1 C6 111.85(19) . . ? C12 C1 C6 111.8(2) . . ? O1 C1 C2 107.49(19) . . ? C12 C1 C2 109.6(2) . . ? C6 C1 C2 110.51(17) . . ? F1 C2 C3 110.02(18) . . ? F1 C2 C1 109.75(18) . . ? C3 C2 C1 110.78(19) . . ? F1 C2 H2 108.8 . . ? C3 C2 H2 108.8 . . ? C1 C2 H2 108.8 . . ? O2 C3 N1 124.4(2) . . ? O2 C3 C2 118.2(2) . . ? N1 C3 C2 117.3(2) . . ? N1 C4 C13 112.28(19) . . ? N1 C4 C5 108.3(2) . . ? C13 C4 C5 112.68(19) . . ? N1 C4 H4 107.8 . . ? C13 C4 H4 107.8 . . ? C5 C4 H4 107.8 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C11 C6 C7 117.9(2) . . ? C11 C6 C1 120.7(2) . . ? C7 C6 C1 121.4(2) . . ? C8 C7 C6 121.0(2) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C9 C8 C7 120.2(2) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C10 C9 C8 119.5(2) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C9 C10 C11 120.4(2) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C10 C11 C6 120.9(2) . . ? C10 C11 H11 119.6 . . ? C6 C11 H11 119.6 . . ? C1 C12 H12A 109.5 . . ? C1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C18 C13 C14 117.9(2) . . ? C18 C13 C4 122.3(2) . . ? C14 C13 C4 119.8(2) . . ? C15 C14 C13 120.8(2) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C16 C15 C14 120.8(2) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C17 C16 C15 118.9(2) . . ? C17 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? C16 C17 C18 120.8(2) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C17 C18 C13 120.8(2) . . ? C17 C18 H18 119.6 . . ? C13 C18 H18 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 O1 C1 C2 F1 -168.85(18) . . . . ? C12 C1 C2 F1 -54.8(2) . . . . ? C6 C1 C2 F1 68.8(2) . . . . ? O1 C1 C2 C3 69.5(2) . . . . ? C12 C1 C2 C3 -176.4(2) . . . . ? C6 C1 C2 C3 -52.8(2) . . . . ? C4 N1 C3 O2 6.9(4) . . . . ? C4 N1 C3 C2 -170.0(2) . . . . ? F1 C2 C3 O2 174.2(2) . . . . ? C1 C2 C3 O2 -64.3(3) . . . . ? F1 C2 C3 N1 -8.8(3) . . . . ? C1 C2 C3 N1 112.7(2) . . . . ? C3 N1 C4 C13 -115.1(2) . . . . ? C3 N1 C4 C5 119.9(2) . . . . ? O1 C1 C6 C11 169.1(2) . . . . ? C12 C1 C6 C11 51.2(3) . . . . ? C2 C1 C6 C11 -71.2(3) . . . . ? O1 C1 C6 C7 -11.9(3) . . . . ? C12 C1 C6 C7 -129.8(2) . . . . ? C2 C1 C6 C7 107.9(2) . . . . ? C11 C6 C7 C8 -1.3(3) . . . . ? C1 C6 C7 C8 179.7(2) . . . . ? C6 C7 C8 C9 0.4(4) . . . . ? C7 C8 C9 C10 0.7(4) . . . . ? C8 C9 C10 C11 -0.8(4) . . . . ? C9 C10 C11 C6 -0.1(4) . . . . ? C7 C6 C11 C10 1.1(3) . . . . ? C1 C6 C11 C10 -179.8(2) . . . . ? N1 C4 C13 C18 2.1(3) . . . . ? C5 C4 C13 C18 124.7(2) . . . . ? N1 C4 C13 C14 -179.7(2) . . . . ? C5 C4 C13 C14 -57.2(3) . . . . ? C18 C13 C14 C15 -0.2(4) . . . . ? C4 C13 C14 C15 -178.5(2) . . . . ? C13 C14 C15 C16 0.1(4) . . . . ? C14 C15 C16 C17 -0.5(4) . . . . ? C15 C16 C17 C18 1.1(4) . . . . ? C16 C17 C18 C13 -1.3(4) . . . . ? C14 C13 C18 C17 0.8(4) . . . . ? C4 C13 C18 C17 179.0(2) . . . . ? 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 O1 H1 O2 0.84 2.13 2.831(2) 140.8 . N1 H1A O2 0.88 2.19 2.985(3) 150.8 3_645 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.191 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.050