Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Angshuman Roychoudhury' _publ_contact_author_address ; Department of Chemistry The University of Liverpool Oxford Street Liverpool Merseyside L697ZD UNITED KINGDOM ; _publ_contact_author_email ANGSHU@LIV.AC.UK _publ_section_title ; Organic fluorine as crystal engineering tool: Evidences from packing features in fluorine substituted isoquinolines ; loop_ _publ_author_name 'Angshuman Roychoudhury' 'T. N. Guru Row' # Attachment '4.cif' data_arc8lt _database_code_depnum_ccdc_archive 'CCDC 256466' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ;1,2-bis-(4-Fluorophenyl)-6-methoxy-1,2,3,4- tetrahydroisoquinoline ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H19 F2 N O' _chemical_formula_weight 351.38 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' N N 0.0061 0.0033 '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 ? _symmetry_space_group_name_H-M ? 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' '-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 12.924(3) _cell_length_b 11.081(2) _cell_length_c 23.689(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3392.7(11) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.56 _exptl_crystal_size_min 0.55 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9448 _exptl_absorpt_correction_T_max 0.9475 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _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 25521 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0124 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3468 _reflns_number_gt 3120 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0461P)^2^+1.4536P] 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 3468 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0373 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.0880 _refine_ls_wR_factor_gt 0.0849 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 -0.18430(5) 0.23450(7) 0.43979(3) 0.02700(19) Uani 1 1 d . . . O1 O 0.06553(7) 0.21148(7) 0.06558(3) 0.0220(2) Uani 1 1 d . . . F2 F 0.33156(7) 0.54336(8) 0.51614(3) 0.0339(2) Uani 1 1 d . . . N2 N 0.19128(7) 0.45298(8) 0.29857(4) 0.0154(2) Uani 1 1 d . . . C7 C 0.11772(9) 0.14395(10) 0.15943(5) 0.0177(2) Uani 1 1 d . . . H7 H 0.1229(11) 0.0621(13) 0.1485(6) 0.020(3) Uiso 1 1 d . . . C11 C 0.05982(8) 0.30029(9) 0.33184(5) 0.0151(2) Uani 1 1 d . . . C10 C 0.10777(8) 0.38518(10) 0.19359(5) 0.0154(2) Uani 1 1 d . . . C3 C 0.11802(9) 0.53836(10) 0.27330(5) 0.0169(2) Uani 1 1 d . . . H3A H 0.1452(10) 0.6216(13) 0.2803(5) 0.017(3) Uiso 1 1 d . . . H3B H 0.0489(11) 0.5327(11) 0.2912(5) 0.015(3) Uiso 1 1 d . . . C8 C 0.13758(8) 0.17607(10) 0.21505(5) 0.0164(2) Uani 1 1 d . . . H8 H 0.1555(10) 0.1137(13) 0.2421(6) 0.018(3) Uiso 1 1 d . . . C17 C 0.22539(9) 0.48124(10) 0.35438(5) 0.0172(2) Uani 1 1 d . . . C4 C 0.10985(9) 0.51698(10) 0.20998(5) 0.0175(2) Uani 1 1 d . . . H4A H 0.0488(11) 0.5580(12) 0.1950(6) 0.020(3) Uiso 1 1 d . . . H4B H 0.1693(11) 0.5548(13) 0.1905(6) 0.025(4) Uiso 1 1 d . . . C22 C 0.17562(9) 0.56457(10) 0.38933(5) 0.0196(2) Uani 1 1 d . . . H22 H 0.1138(11) 0.6065(13) 0.3761(6) 0.025(4) Uiso 1 1 d . . . C15 C -0.12466(9) 0.30268(10) 0.35134(5) 0.0179(2) Uani 1 1 d . . . H15 H -0.1946(11) 0.3178(13) 0.3402(6) 0.022(3) Uiso 1 1 d . . . C6 C 0.09044(8) 0.23335(10) 0.12093(5) 0.0171(2) Uani 1 1 d . . . C14 C -0.10398(9) 0.25667(10) 0.40413(5) 0.0190(2) Uani 1 1 d . . . C9 C 0.13251(8) 0.29568(10) 0.23283(5) 0.0149(2) Uani 1 1 d . . . C1 C 0.15329(8) 0.32623(9) 0.29395(5) 0.0148(2) Uani 1 1 d . . . H1 H 0.2101(10) 0.2743(11) 0.3076(5) 0.011(3) Uiso 1 1 d . . . C5 C 0.08658(8) 0.35349(10) 0.13801(5) 0.0169(2) Uani 1 1 d . . . H5 H 0.0705(10) 0.4162(12) 0.1103(5) 0.017(3) Uiso 1 1 d . . . C19 C 0.34803(10) 0.44096(12) 0.42957(5) 0.0236(3) Uani 1 1 d . . . H19 H 0.4091(12) 0.3970(14) 0.4439(6) 0.032(4) Uiso 1 1 d . . . C16 C -0.04188(9) 0.32331(10) 0.31496(5) 0.0161(2) Uani 1 1 d . . . H16 H -0.0565(10) 0.3521(12) 0.2767(5) 0.014(3) Uiso 1 1 d . . . C20 C 0.29634(10) 0.52330(11) 0.46280(5) 0.0239(3) Uani 1 1 d . . . C12 C 0.07643(9) 0.25384(11) 0.38573(5) 0.0201(2) Uani 1 1 d . . . H12 H 0.1461(12) 0.2352(13) 0.3979(6) 0.023(3) Uiso 1 1 d . . . C21 C 0.21177(10) 0.58653(11) 0.44383(5) 0.0236(3) Uani 1 1 d . . . H21 H 0.1777(12) 0.6440(14) 0.4681(7) 0.032(4) Uiso 1 1 d . . . C18 C 0.31301(9) 0.42150(11) 0.37502(5) 0.0208(3) Uani 1 1 d . . . H18 H 0.3500(11) 0.3644(14) 0.3499(6) 0.024(4) Uiso 1 1 d . . . C13 C -0.00530(10) 0.23071(11) 0.42243(5) 0.0219(3) Uani 1 1 d . . . H13 H 0.0054(11) 0.1979(12) 0.4597(6) 0.025(4) Uiso 1 1 d . . . C23 C 0.08904(11) 0.09381(12) 0.04452(5) 0.0251(3) Uani 1 1 d . . . H23A H 0.1629(13) 0.0734(14) 0.0521(6) 0.030(4) Uiso 1 1 d . . . H23B H 0.0762(11) 0.0967(14) 0.0038(6) 0.027(4) Uiso 1 1 d . . . H23C H 0.0448(12) 0.0320(13) 0.0623(6) 0.025(4) 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 F1 0.0227(4) 0.0343(4) 0.0240(4) -0.0009(3) 0.0092(3) -0.0048(3) O1 0.0264(5) 0.0224(4) 0.0171(4) -0.0044(3) -0.0031(3) -0.0003(3) F2 0.0424(5) 0.0426(5) 0.0168(4) -0.0032(3) -0.0061(3) -0.0104(4) N2 0.0153(5) 0.0143(4) 0.0166(5) -0.0008(3) -0.0012(3) -0.0004(3) C7 0.0165(6) 0.0148(5) 0.0219(6) -0.0024(4) 0.0028(4) -0.0015(4) C11 0.0165(5) 0.0121(5) 0.0168(5) -0.0016(4) 0.0011(4) -0.0006(4) C10 0.0115(5) 0.0159(5) 0.0188(5) 0.0002(4) 0.0021(4) 0.0001(4) C3 0.0168(6) 0.0137(5) 0.0202(6) -0.0006(4) 0.0000(4) 0.0002(4) C8 0.0139(5) 0.0160(5) 0.0192(6) 0.0017(4) 0.0021(4) 0.0001(4) C17 0.0166(6) 0.0182(5) 0.0169(5) 0.0000(4) 0.0017(4) -0.0051(4) C4 0.0190(6) 0.0146(5) 0.0191(6) 0.0017(4) -0.0020(4) 0.0004(4) C22 0.0198(6) 0.0192(5) 0.0198(6) -0.0002(4) 0.0024(4) -0.0038(5) C15 0.0150(5) 0.0154(5) 0.0233(6) -0.0041(4) -0.0009(4) -0.0004(4) C6 0.0135(5) 0.0217(6) 0.0162(5) -0.0019(4) 0.0014(4) -0.0023(4) C14 0.0198(6) 0.0178(5) 0.0194(6) -0.0040(4) 0.0071(4) -0.0040(4) C9 0.0113(5) 0.0166(5) 0.0167(5) -0.0002(4) 0.0020(4) -0.0007(4) C1 0.0139(5) 0.0134(5) 0.0171(5) 0.0000(4) 0.0000(4) 0.0009(4) C5 0.0143(5) 0.0183(5) 0.0182(6) 0.0019(4) -0.0001(4) 0.0000(4) C19 0.0199(6) 0.0291(6) 0.0218(6) 0.0036(5) -0.0027(5) -0.0051(5) C16 0.0181(5) 0.0142(5) 0.0160(5) -0.0009(4) -0.0012(4) -0.0004(4) C20 0.0289(7) 0.0287(6) 0.0141(5) 0.0007(5) -0.0015(5) -0.0125(5) C12 0.0178(6) 0.0216(6) 0.0209(6) 0.0021(5) -0.0011(5) 0.0008(4) C21 0.0294(7) 0.0223(6) 0.0193(6) -0.0032(5) 0.0059(5) -0.0061(5) C18 0.0177(6) 0.0238(6) 0.0208(6) -0.0019(5) 0.0003(4) -0.0018(5) C13 0.0250(6) 0.0242(6) 0.0166(6) 0.0031(5) 0.0007(5) -0.0008(5) C23 0.0274(7) 0.0262(6) 0.0216(6) -0.0088(5) -0.0012(5) 0.0004(5) _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 C14 1.3607(13) . ? O1 C6 1.3717(14) . ? O1 C23 1.4288(15) . ? F2 C20 1.3613(14) . ? N2 C17 1.4284(14) . ? N2 C3 1.4664(14) . ? N2 C1 1.4919(14) . ? C7 C8 1.3888(16) . ? C7 C6 1.3920(16) . ? C7 H7 0.946(14) . ? C11 C12 1.3932(16) . ? C11 C16 1.3973(16) . ? C11 C1 1.5322(15) . ? C10 C5 1.3900(16) . ? C10 C9 1.3963(16) . ? C10 C4 1.5114(15) . ? C3 C4 1.5222(16) . ? C3 H3A 1.000(14) . ? C3 H3B 0.991(14) . ? C8 C9 1.3922(16) . ? C8 H8 0.971(14) . ? C17 C22 1.3970(16) . ? C17 C18 1.3998(17) . ? C4 H4A 0.977(14) . ? C4 H4B 0.990(15) . ? C22 C21 1.3945(17) . ? C22 H22 0.976(15) . ? C15 C14 1.3767(17) . ? C15 C16 1.3927(16) . ? C15 H15 0.957(14) . ? C6 C5 1.3922(16) . ? C14 C13 1.3774(17) . ? C9 C1 1.5110(15) . ? C1 H1 0.987(13) . ? C5 H5 0.979(13) . ? C19 C20 1.3779(19) . ? C19 C18 1.3860(17) . ? C19 H19 0.987(16) . ? C16 H16 0.978(13) . ? C20 C21 1.3739(19) . ? C12 C13 1.3918(17) . ? C12 H12 0.967(15) . ? C21 H21 0.964(16) . ? C18 H18 0.991(15) . ? C13 H13 0.965(15) . ? C23 H23A 0.998(16) . ? C23 H23B 0.980(15) . ? C23 H23C 0.987(15) . ? 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 C6 O1 C23 116.42(9) . . ? C17 N2 C3 115.83(9) . . ? C17 N2 C1 112.09(9) . . ? C3 N2 C1 111.40(8) . . ? C8 C7 C6 119.08(11) . . ? C8 C7 H7 119.5(8) . . ? C6 C7 H7 121.4(8) . . ? C12 C11 C16 118.33(10) . . ? C12 C11 C1 118.99(10) . . ? C16 C11 C1 122.67(10) . . ? C5 C10 C9 119.75(10) . . ? C5 C10 C4 119.41(10) . . ? C9 C10 C4 120.75(10) . . ? N2 C3 C4 110.29(9) . . ? N2 C3 H3A 107.5(8) . . ? C4 C3 H3A 109.4(7) . . ? N2 C3 H3B 111.5(7) . . ? C4 C3 H3B 110.4(7) . . ? H3A C3 H3B 107.7(10) . . ? C7 C8 C9 121.48(10) . . ? C7 C8 H8 119.2(8) . . ? C9 C8 H8 119.3(8) . . ? C22 C17 C18 118.57(11) . . ? C22 C17 N2 123.45(10) . . ? C18 C17 N2 117.98(10) . . ? C10 C4 C3 113.88(9) . . ? C10 C4 H4A 110.0(8) . . ? C3 C4 H4A 110.0(8) . . ? C10 C4 H4B 107.6(8) . . ? C3 C4 H4B 109.9(8) . . ? H4A C4 H4B 105.1(11) . . ? C21 C22 C17 120.64(12) . . ? C21 C22 H22 119.3(8) . . ? C17 C22 H22 120.1(8) . . ? C14 C15 C16 118.28(11) . . ? C14 C15 H15 119.9(8) . . ? C16 C15 H15 121.8(8) . . ? O1 C6 C7 124.06(10) . . ? O1 C6 C5 115.99(10) . . ? C7 C6 C5 119.95(11) . . ? F1 C14 C15 118.86(10) . . ? F1 C14 C13 118.25(10) . . ? C15 C14 C13 122.88(11) . . ? C8 C9 C10 119.06(10) . . ? C8 C9 C1 119.65(10) . . ? C10 C9 C1 121.30(10) . . ? N2 C1 C9 109.86(9) . . ? N2 C1 C11 113.15(9) . . ? C9 C1 C11 112.29(9) . . ? N2 C1 H1 106.2(7) . . ? C9 C1 H1 108.4(7) . . ? C11 C1 H1 106.6(7) . . ? C10 C5 C6 120.65(10) . . ? C10 C5 H5 119.9(8) . . ? C6 C5 H5 119.4(8) . . ? C20 C19 C18 118.51(12) . . ? C20 C19 H19 121.2(9) . . ? C18 C19 H19 120.3(9) . . ? C15 C16 C11 121.04(10) . . ? C15 C16 H16 118.5(7) . . ? C11 C16 H16 120.4(7) . . ? F2 C20 C21 119.10(11) . . ? F2 C20 C19 118.45(12) . . ? C21 C20 C19 122.45(11) . . ? C13 C12 C11 121.56(11) . . ? C13 C12 H12 118.8(8) . . ? C11 C12 H12 119.6(8) . . ? C20 C21 C22 118.71(12) . . ? C20 C21 H21 120.4(9) . . ? C22 C21 H21 120.9(9) . . ? C19 C18 C17 121.08(11) . . ? C19 C18 H18 120.1(8) . . ? C17 C18 H18 118.8(8) . . ? C14 C13 C12 117.89(11) . . ? C14 C13 H13 120.0(9) . . ? C12 C13 H13 122.2(9) . . ? O1 C23 H23A 110.3(9) . . ? O1 C23 H23B 106.1(9) . . ? H23A C23 H23B 110.4(12) . . ? O1 C23 H23C 111.2(8) . . ? H23A C23 H23C 108.6(12) . . ? H23B C23 H23C 110.2(12) . . ? 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 C17 N2 C3 C4 165.27(9) . . . . ? C1 N2 C3 C4 -65.06(11) . . . . ? C6 C7 C8 C9 -1.11(17) . . . . ? C3 N2 C17 C22 15.96(15) . . . . ? C1 N2 C17 C22 -113.39(12) . . . . ? C3 N2 C17 C18 -164.42(10) . . . . ? C1 N2 C17 C18 66.24(13) . . . . ? C5 C10 C4 C3 171.41(10) . . . . ? C9 C10 C4 C3 -12.18(15) . . . . ? N2 C3 C4 C10 40.99(13) . . . . ? C18 C17 C22 C21 -0.80(17) . . . . ? N2 C17 C22 C21 178.83(10) . . . . ? C23 O1 C6 C7 -12.67(16) . . . . ? C23 O1 C6 C5 167.77(10) . . . . ? C8 C7 C6 O1 -177.53(10) . . . . ? C8 C7 C6 C5 2.02(16) . . . . ? C16 C15 C14 F1 -179.08(9) . . . . ? C16 C15 C14 C13 0.23(17) . . . . ? C7 C8 C9 C10 -0.58(17) . . . . ? C7 C8 C9 C1 179.16(10) . . . . ? C5 C10 C9 C8 1.35(16) . . . . ? C4 C10 C9 C8 -175.04(10) . . . . ? C5 C10 C9 C1 -178.39(10) . . . . ? C4 C10 C9 C1 5.22(16) . . . . ? C17 N2 C1 C9 -172.06(9) . . . . ? C3 N2 C1 C9 56.33(11) . . . . ? C17 N2 C1 C11 61.57(12) . . . . ? C3 N2 C1 C11 -70.04(12) . . . . ? C8 C9 C1 N2 154.03(10) . . . . ? C10 C9 C1 N2 -26.23(13) . . . . ? C8 C9 C1 C11 -79.11(12) . . . . ? C10 C9 C1 C11 100.62(12) . . . . ? C12 C11 C1 N2 -92.80(12) . . . . ? C16 C11 C1 N2 86.04(12) . . . . ? C12 C11 C1 C9 142.14(10) . . . . ? C16 C11 C1 C9 -39.02(14) . . . . ? C9 C10 C5 C6 -0.44(16) . . . . ? C4 C10 C5 C6 176.00(10) . . . . ? O1 C6 C5 C10 178.32(10) . . . . ? C7 C6 C5 C10 -1.27(17) . . . . ? C14 C15 C16 C11 -1.26(16) . . . . ? C12 C11 C16 C15 1.22(16) . . . . ? C1 C11 C16 C15 -177.63(10) . . . . ? C18 C19 C20 F2 -179.24(10) . . . . ? C18 C19 C20 C21 -0.04(18) . . . . ? C16 C11 C12 C13 -0.16(17) . . . . ? C1 C11 C12 C13 178.73(10) . . . . ? F2 C20 C21 C22 -179.39(10) . . . . ? C19 C20 C21 C22 1.41(18) . . . . ? C17 C22 C21 C20 -0.97(17) . . . . ? C20 C19 C18 C17 -1.81(18) . . . . ? C22 C17 C18 C19 2.21(17) . . . . ? N2 C17 C18 C19 -177.44(10) . . . . ? F1 C14 C13 C12 -179.89(10) . . . . ? C15 C14 C13 C12 0.80(18) . . . . ? C11 C12 C13 C14 -0.82(18) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.344 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.039 # Attachment '5.cif' data_arc8lt_5 _database_code_depnum_ccdc_archive 'CCDC 256467' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; 1-(3-Fluorophenyl)- 2- (4-Fluorophenyl)-6-methoxy-1,2,3,4- tetrahydroisoquinoline ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H19 F2 N O' _chemical_formula_weight 351.38 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' N N 0.0061 0.0033 '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 ? _symmetry_space_group_name_H-M ? 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' '-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 10.728(3) _cell_length_b 8.023(2) _cell_length_c 39.710(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3417.9(17) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _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 1.366 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9711 _exptl_absorpt_correction_T_max 0.9902 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _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 24463 _diffrn_reflns_av_R_equivalents 0.1346 _diffrn_reflns_av_sigmaI/netI 0.0771 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -47 _diffrn_reflns_limit_l_max 47 _diffrn_reflns_theta_min 1.03 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3129 _reflns_number_gt 1841 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0651P)^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 3129 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1118 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1348 _refine_ls_wR_factor_gt 0.1017 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 F2 F -0.16721(15) 1.0257(2) 0.26763(4) 0.0343(5) Uani 1 1 d . . . F1 F -0.17023(15) 0.1838(2) 0.07021(4) 0.0354(5) Uani 1 1 d . . . O1 O 0.20853(19) 0.9528(3) 0.01209(5) 0.0311(6) Uani 1 1 d . . . N2 N 0.05823(19) 0.7244(3) 0.15799(6) 0.0184(6) Uani 1 1 d . . . C18 C 0.0700(3) 0.8893(3) 0.20903(7) 0.0196(7) Uani 1 1 d . . . C1 C -0.0157(3) 0.6768(3) 0.12855(7) 0.0183(7) Uani 1 1 d . . . C10 C 0.1709(3) 0.7333(3) 0.09307(7) 0.0189(7) Uani 1 1 d . . . C6 C 0.1603(3) 0.8798(4) 0.04053(7) 0.0221(7) Uani 1 1 d . . . C21 C -0.1837(3) 0.8547(4) 0.21932(8) 0.0225(7) Uani 1 1 d . . . C8 C -0.0264(3) 0.8236(3) 0.07172(7) 0.0211(7) Uani 1 1 d . . . C9 C 0.0424(2) 0.7448(3) 0.09656(7) 0.0176(7) Uani 1 1 d . . . C14 C -0.1130(3) 0.1525(4) 0.12688(8) 0.0246(7) Uani 1 1 d . . . C22 C -0.1275(3) 0.7778(4) 0.19199(8) 0.0201(7) Uani 1 1 d . . . C4 C 0.2382(3) 0.6530(4) 0.12195(8) 0.0215(7) Uani 1 1 d . . . C20 C -0.1114(3) 0.9486(4) 0.24066(7) 0.0234(7) Uani 1 1 d . . . C11 C -0.0436(2) 0.4894(3) 0.12755(7) 0.0184(7) Uani 1 1 d . . . C19 C 0.0146(3) 0.9666(4) 0.23632(8) 0.0213(7) Uani 1 1 d . . . C16 C -0.0907(3) 0.4171(4) 0.09825(8) 0.0216(7) Uani 1 1 d . . . C5 C 0.2304(3) 0.8007(3) 0.06504(7) 0.0198(7) Uani 1 1 d . . . C17 C 0.0015(2) 0.7972(3) 0.18578(7) 0.0169(6) Uani 1 1 d . . . C7 C 0.0314(3) 0.8910(4) 0.04381(8) 0.0233(7) Uani 1 1 d . . . C12 C -0.0306(3) 0.3905(4) 0.15613(8) 0.0215(7) Uani 1 1 d . . . C3 C 0.1942(3) 0.7269(4) 0.15519(8) 0.0202(7) Uani 1 1 d . . . C15 C -0.1234(3) 0.2516(4) 0.09889(8) 0.0242(7) Uani 1 1 d . . . C13 C -0.0648(3) 0.2247(4) 0.15566(9) 0.0245(7) Uani 1 1 d . . . C23 C 0.3406(3) 0.9473(5) 0.00778(10) 0.0368(9) Uani 1 1 d . . . H18 H 0.155(2) 0.904(3) 0.2061(6) 0.007(6) Uiso 1 1 d . . . H5 H 0.319(2) 0.788(3) 0.0623(6) 0.014(7) Uiso 1 1 d . . . H8 H -0.120(2) 0.829(3) 0.0749(6) 0.014(7) Uiso 1 1 d . . . H22 H -0.180(2) 0.708(4) 0.1770(7) 0.024(8) Uiso 1 1 d . . . H4B H 0.221(2) 0.533(4) 0.1207(7) 0.019(7) Uiso 1 1 d . . . H13 H -0.056(2) 0.163(3) 0.1750(7) 0.013(7) Uiso 1 1 d . . . H4AA H 0.328(3) 0.666(3) 0.1186(7) 0.022(8) Uiso 1 1 d . . . H7 H -0.010(2) 0.948(3) 0.0265(7) 0.015(7) Uiso 1 1 d . . . H23A H 0.387(3) 1.006(4) 0.0266(8) 0.032(9) Uiso 1 1 d . . . H1 H -0.101(2) 0.735(3) 0.1292(7) 0.024(8) Uiso 1 1 d . . . H21 H -0.273(3) 0.844(4) 0.2225(8) 0.039(9) Uiso 1 1 d . . . H16 H -0.097(2) 0.482(3) 0.0760(7) 0.021(7) Uiso 1 1 d . . . H23B H 0.360(3) 1.012(4) -0.0124(9) 0.039(9) Uiso 1 1 d . . . H3A H 0.231(2) 0.847(4) 0.1554(7) 0.027(8) Uiso 1 1 d . . . H3B H 0.230(2) 0.662(3) 0.1735(7) 0.017(7) Uiso 1 1 d . . . H14 H -0.136(2) 0.040(4) 0.1246(7) 0.029(8) Uiso 1 1 d . . . H12 H 0.002(2) 0.438(3) 0.1744(7) 0.018(8) Uiso 1 1 d . . . H23C H 0.368(3) 0.829(4) 0.0075(8) 0.037(9) Uiso 1 1 d . . . H19 H 0.062(2) 1.038(4) 0.2510(7) 0.030(8) 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 F2 0.0360(10) 0.0413(11) 0.0256(11) -0.0161(9) 0.0090(8) -0.0062(8) F1 0.0428(11) 0.0262(10) 0.0370(12) -0.0105(9) -0.0114(9) -0.0008(8) O1 0.0340(13) 0.0416(14) 0.0178(13) 0.0094(10) 0.0048(9) -0.0023(10) N2 0.0194(12) 0.0218(13) 0.0141(14) -0.0044(11) -0.0004(11) -0.0016(10) C18 0.0187(15) 0.0183(15) 0.0217(19) 0.0013(13) 0.0009(13) -0.0020(12) C1 0.0197(15) 0.0199(16) 0.0153(17) 0.0005(13) -0.0018(12) 0.0006(12) C10 0.0285(16) 0.0146(14) 0.0135(17) -0.0030(12) -0.0023(13) 0.0024(12) C6 0.0317(17) 0.0203(15) 0.0144(18) -0.0008(13) 0.0034(14) -0.0029(13) C21 0.0221(17) 0.0237(17) 0.0217(19) -0.0013(13) 0.0036(14) -0.0004(13) C8 0.0234(16) 0.0213(15) 0.0186(18) -0.0016(14) -0.0031(13) -0.0012(12) C9 0.0245(16) 0.0132(14) 0.0151(17) -0.0032(12) 0.0000(13) -0.0013(12) C14 0.0244(16) 0.0154(16) 0.034(2) -0.0015(15) 0.0045(14) 0.0007(13) C22 0.0236(16) 0.0213(16) 0.0154(18) -0.0024(13) -0.0005(13) -0.0025(13) C4 0.0210(17) 0.0237(18) 0.0197(18) 0.0005(14) 0.0008(13) 0.0036(13) C20 0.0315(18) 0.0240(16) 0.0147(17) -0.0048(13) 0.0062(14) 0.0020(13) C11 0.0171(15) 0.0173(15) 0.0207(17) -0.0013(13) 0.0016(12) 0.0028(11) C19 0.0230(16) 0.0216(15) 0.0194(18) -0.0001(14) -0.0041(14) -0.0027(13) C16 0.0268(17) 0.0217(16) 0.0162(18) -0.0003(14) -0.0009(13) 0.0025(12) C5 0.0234(16) 0.0203(15) 0.0158(17) -0.0037(14) 0.0016(13) -0.0002(12) C17 0.0249(16) 0.0135(14) 0.0124(16) 0.0027(12) -0.0006(12) 0.0010(12) C7 0.0327(18) 0.0222(16) 0.0151(18) 0.0059(14) -0.0030(14) 0.0014(13) C12 0.0229(16) 0.0227(16) 0.0190(18) -0.0023(15) 0.0022(14) -0.0002(12) C3 0.0193(15) 0.0217(16) 0.0196(18) 0.0046(14) 0.0004(14) 0.0004(12) C15 0.0234(16) 0.0221(15) 0.027(2) -0.0101(14) -0.0030(14) 0.0016(12) C13 0.0271(17) 0.0224(16) 0.024(2) 0.0082(15) 0.0055(15) 0.0040(13) C23 0.037(2) 0.046(2) 0.027(2) 0.0090(19) 0.0114(17) 0.0026(18) _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 F2 C20 1.374(3) . ? F1 C15 1.359(3) . ? O1 C6 1.373(3) . ? O1 C23 1.427(4) . ? N2 C17 1.389(3) . ? N2 C1 1.463(3) . ? N2 C3 1.463(3) . ? C18 C19 1.382(4) . ? C18 C17 1.392(4) . ? C18 H18 0.93(2) . ? C1 C9 1.517(4) . ? C1 C11 1.533(4) . ? C1 H1 1.03(3) . ? C10 C9 1.389(4) . ? C10 C5 1.393(4) . ? C10 C4 1.501(4) . ? C6 C5 1.384(4) . ? C6 C7 1.391(4) . ? C21 C20 1.374(4) . ? C21 C22 1.387(4) . ? C21 H21 0.97(3) . ? C8 C7 1.380(4) . ? C8 C9 1.385(4) . ? C8 H8 1.01(2) . ? C14 C15 1.371(4) . ? C14 C13 1.382(5) . ? C14 H14 0.94(3) . ? C22 C17 1.414(4) . ? C22 H22 0.99(3) . ? C4 C3 1.522(4) . ? C4 H4B 0.98(3) . ? C4 H4AA 0.98(3) . ? C20 C19 1.371(4) . ? C11 C12 1.392(4) . ? C11 C16 1.394(4) . ? C19 H19 0.96(3) . ? C16 C15 1.374(4) . ? C16 H16 1.03(3) . ? C5 H5 0.96(2) . ? C7 H7 0.94(3) . ? C12 C13 1.379(4) . ? C12 H12 0.89(3) . ? C3 H3A 1.04(3) . ? C3 H3B 0.97(3) . ? C13 H13 0.92(3) . ? C23 H23A 1.01(3) . ? C23 H23B 0.98(3) . ? C23 H23C 0.99(3) . ? 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 C6 O1 C23 117.3(2) . . ? C17 N2 C1 120.5(2) . . ? C17 N2 C3 119.4(2) . . ? C1 N2 C3 118.9(2) . . ? C19 C18 C17 122.1(3) . . ? C19 C18 H18 117.6(16) . . ? C17 C18 H18 120.3(16) . . ? N2 C1 C9 110.6(2) . . ? N2 C1 C11 112.5(2) . . ? C9 C1 C11 114.3(2) . . ? N2 C1 H1 110.1(15) . . ? C9 C1 H1 102.9(15) . . ? C11 C1 H1 105.9(16) . . ? C9 C10 C5 120.6(3) . . ? C9 C10 C4 115.5(3) . . ? C5 C10 C4 123.9(3) . . ? O1 C6 C5 124.7(3) . . ? O1 C6 C7 115.1(3) . . ? C5 C6 C7 120.3(3) . . ? C20 C21 C22 118.8(3) . . ? C20 C21 H21 121.8(18) . . ? C22 C21 H21 119.4(18) . . ? C7 C8 C9 120.7(3) . . ? C7 C8 H8 121.8(14) . . ? C9 C8 H8 117.4(15) . . ? C8 C9 C10 119.2(3) . . ? C8 C9 C1 122.8(3) . . ? C10 C9 C1 117.9(2) . . ? C15 C14 C13 117.2(3) . . ? C15 C14 H14 117.1(18) . . ? C13 C14 H14 125.6(18) . . ? C21 C22 C17 120.9(3) . . ? C21 C22 H22 118.4(16) . . ? C17 C22 H22 120.7(15) . . ? C10 C4 C3 110.2(2) . . ? C10 C4 H4B 107.0(16) . . ? C3 C4 H4B 111.5(16) . . ? C10 C4 H4AA 108.7(16) . . ? C3 C4 H4AA 112.5(16) . . ? H4B C4 H4AA 107(2) . . ? C19 C20 F2 118.7(3) . . ? C19 C20 C21 122.5(3) . . ? F2 C20 C21 118.8(3) . . ? C12 C11 C16 118.6(3) . . ? C12 C11 C1 121.2(3) . . ? C16 C11 C1 120.0(3) . . ? C20 C19 C18 118.4(3) . . ? C20 C19 H19 120.3(17) . . ? C18 C19 H19 121.2(17) . . ? C15 C16 C11 118.6(3) . . ? C15 C16 H16 119.1(15) . . ? C11 C16 H16 122.2(15) . . ? C6 C5 C10 119.4(3) . . ? C6 C5 H5 120.5(15) . . ? C10 C5 H5 120.1(15) . . ? N2 C17 C18 121.3(2) . . ? N2 C17 C22 121.4(2) . . ? C18 C17 C22 117.3(3) . . ? C8 C7 C6 119.8(3) . . ? C8 C7 H7 124.3(16) . . ? C6 C7 H7 116.0(16) . . ? C13 C12 C11 120.8(3) . . ? C13 C12 H12 121.7(18) . . ? C11 C12 H12 117.4(18) . . ? N2 C3 C4 111.7(2) . . ? N2 C3 H3A 112.7(15) . . ? C4 C3 H3A 104.6(15) . . ? N2 C3 H3B 109.0(15) . . ? C4 C3 H3B 108.5(15) . . ? H3A C3 H3B 110(2) . . ? F1 C15 C14 118.5(3) . . ? F1 C15 C16 117.8(3) . . ? C14 C15 C16 123.7(3) . . ? C12 C13 C14 121.0(3) . . ? C12 C13 H13 118.8(16) . . ? C14 C13 H13 120.2(16) . . ? O1 C23 H23A 112.7(17) . . ? O1 C23 H23B 106.9(18) . . ? H23A C23 H23B 105(2) . . ? O1 C23 H23C 109.1(17) . . ? H23A C23 H23C 108(3) . . ? H23B C23 H23C 116(3) . . ? 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 C17 N2 C1 C9 129.7(3) . . . . ? C3 N2 C1 C9 -37.6(3) . . . . ? C17 N2 C1 C11 -101.1(3) . . . . ? C3 N2 C1 C11 91.5(3) . . . . ? C23 O1 C6 C5 -0.5(4) . . . . ? C23 O1 C6 C7 179.0(3) . . . . ? C7 C8 C9 C10 -0.3(4) . . . . ? C7 C8 C9 C1 176.7(3) . . . . ? C5 C10 C9 C8 0.3(4) . . . . ? C4 C10 C9 C8 177.3(3) . . . . ? C5 C10 C9 C1 -176.9(2) . . . . ? C4 C10 C9 C1 0.1(4) . . . . ? N2 C1 C9 C8 -134.1(3) . . . . ? C11 C1 C9 C8 97.6(3) . . . . ? N2 C1 C9 C10 42.9(3) . . . . ? C11 C1 C9 C10 -85.3(3) . . . . ? C20 C21 C22 C17 -1.0(4) . . . . ? C9 C10 C4 C3 -47.8(3) . . . . ? C5 C10 C4 C3 129.1(3) . . . . ? C22 C21 C20 C19 -1.2(5) . . . . ? C22 C21 C20 F2 179.6(3) . . . . ? N2 C1 C11 C12 17.1(4) . . . . ? C9 C1 C11 C12 144.4(3) . . . . ? N2 C1 C11 C16 -167.1(2) . . . . ? C9 C1 C11 C16 -39.8(4) . . . . ? F2 C20 C19 C18 -179.7(3) . . . . ? C21 C20 C19 C18 1.1(4) . . . . ? C17 C18 C19 C20 1.2(4) . . . . ? C12 C11 C16 C15 0.6(4) . . . . ? C1 C11 C16 C15 -175.3(2) . . . . ? O1 C6 C5 C10 179.1(3) . . . . ? C7 C6 C5 C10 -0.4(4) . . . . ? C9 C10 C5 C6 0.1(4) . . . . ? C4 C10 C5 C6 -176.7(3) . . . . ? C1 N2 C17 C18 -159.7(2) . . . . ? C3 N2 C17 C18 7.5(4) . . . . ? C1 N2 C17 C22 21.7(4) . . . . ? C3 N2 C17 C22 -171.1(3) . . . . ? C19 C18 C17 N2 178.2(3) . . . . ? C19 C18 C17 C22 -3.2(4) . . . . ? C21 C22 C17 N2 -178.3(3) . . . . ? C21 C22 C17 C18 3.1(4) . . . . ? C9 C8 C7 C6 0.0(4) . . . . ? O1 C6 C7 C8 -179.2(3) . . . . ? C5 C6 C7 C8 0.3(4) . . . . ? C16 C11 C12 C13 -0.7(4) . . . . ? C1 C11 C12 C13 175.2(3) . . . . ? C17 N2 C3 C4 -175.7(2) . . . . ? C1 N2 C3 C4 -8.3(4) . . . . ? C10 C4 C3 N2 51.4(3) . . . . ? C13 C14 C15 F1 179.8(2) . . . . ? C13 C14 C15 C16 -1.2(4) . . . . ? C11 C16 C15 F1 179.4(2) . . . . ? C11 C16 C15 C14 0.4(4) . . . . ? C11 C12 C13 C14 -0.2(4) . . . . ? C15 C14 C13 C12 1.1(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.233 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.051 # Attachment '6.cif' data_arc11ltm _database_code_depnum_ccdc_archive 'CCDC 256468' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ;1,2-bis-(3-Fluorophenyl)-6-methoxy-1,2,3,4- tetrahydroisoquinoline ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H18 F2 N O' _chemical_formula_weight 350.37 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' N N 0.0061 0.0033 '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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 16.628(6) _cell_length_b 45.589(12) _cell_length_c 9.044(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6856(4) _cell_formula_units_Z 16 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2928 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9759 _exptl_absorpt_correction_T_max 0.9903 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _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 16402 _diffrn_reflns_av_R_equivalents 0.0181 _diffrn_reflns_av_sigmaI/netI 0.0140 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -54 _diffrn_reflns_limit_k_max 54 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3126 _reflns_number_gt 3066 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0533P)^2^+2.9247P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(6) _refine_ls_number_reflns 3126 _refine_ls_number_parameters 321 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0283 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0757 _refine_ls_wR_factor_gt 0.0750 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 F1A F 0.37878(14) 0.06228(5) 0.7260(3) 0.0225(5) Uani 0.30 1 d P . . F1B F 0.19401(9) 0.11937(3) 0.92607(15) 0.0396(3) Uani 0.70 1 d P . . F2A F 0.10169(16) -0.08534(5) 0.7063(3) 0.0433(7) Uani 0.37 1 d P . . F2B F 0.07700(9) -0.01226(3) 1.04050(16) 0.0377(3) Uani 0.63 1 d P . . O1 O 0.03131(6) 0.10506(2) 0.04290(11) 0.0298(2) Uani 1 1 d . . . N2 N 0.13265(7) 0.01302(2) 0.54214(14) 0.0252(2) Uani 1 1 d . . . C9 C 0.08790(8) 0.06011(3) 0.42965(15) 0.0238(3) Uani 1 1 d . . . C5 C 0.09951(8) 0.06753(3) 0.16653(15) 0.0240(3) Uani 1 1 d . . . C22 C 0.10463(8) 0.00083(3) 0.79968(17) 0.0278(3) Uani 1 1 d . . . C10 C 0.12082(8) 0.05224(3) 0.29354(15) 0.0235(3) Uani 1 1 d . . . C7 C 0.01617(8) 0.09996(3) 0.30999(16) 0.0250(3) Uani 1 1 d . . . C8 C 0.03560(8) 0.08396(3) 0.43611(16) 0.0257(3) Uani 1 1 d . . . C14 C 0.28968(11) 0.09051(3) 0.82482(17) 0.0373(4) Uani 1 1 d . . . C1 C 0.10916(8) 0.04358(3) 0.57007(16) 0.0243(3) Uani 1 1 d . . . C17 C 0.11862(8) -0.00763(3) 0.65153(16) 0.0249(3) Uani 1 1 d . . . C4 C 0.17812(9) 0.02684(3) 0.29133(16) 0.0277(3) Uani 1 1 d . . . C20 C 0.08853(10) -0.05011(4) 0.87437(19) 0.0370(4) Uani 1 1 d . . . C12 C 0.25447(9) 0.05289(3) 0.64756(16) 0.0273(3) Uani 1 1 d . . . C11 C 0.17347(9) 0.05998(3) 0.65937(15) 0.0256(3) Uani 1 1 d . . . C6 C 0.04769(8) 0.09141(3) 0.17428(15) 0.0240(3) Uani 1 1 d . . . C23 C -0.01484(10) 0.13137(4) 0.04881(19) 0.0373(4) Uani 1 1 d . . . C19 C 0.10410(9) -0.05808(4) 0.7304(2) 0.0368(4) Uani 1 1 d . . . C21 C 0.08981(8) -0.02036(3) 0.90512(18) 0.0325(3) Uani 1 1 d . . . C3 C 0.14801(9) 0.00262(3) 0.39174(17) 0.0282(3) Uani 1 1 d . . . C18 C 0.11851(9) -0.03793(3) 0.61936(18) 0.0310(3) Uani 1 1 d . . . C13 C 0.31166(11) 0.06813(3) 0.72950(17) 0.0364(4) Uani 1 1 d . . . C16 C 0.15082(10) 0.08253(3) 0.75536(16) 0.0310(3) Uani 1 1 d . . . C15 C 0.20945(12) 0.09718(3) 0.83549(16) 0.0380(4) Uani 1 1 d . . . H1 H 0.0606(10) 0.0431(3) 0.6317(18) 0.022(4) Uiso 1 1 d . . . H16 H 0.0949(10) 0.0882(3) 0.765(2) 0.029(4) Uiso 1 1 d . . . H12 H 0.2696(10) 0.0364(3) 0.5843(18) 0.026(4) Uiso 1 1 d . . . H3A H 0.1871(11) -0.0124(4) 0.399(2) 0.037(5) Uiso 1 1 d . . . H31 H 0.1056(9) 0.0226(4) 0.8308(19) 0.021(4) Uiso 1 1 d . . . H5 H 0.1213(10) 0.0620(4) 0.072(2) 0.030(4) Uiso 1 1 d . . . H8 H 0.0108(10) 0.0886(3) 0.5287(18) 0.026(4) Uiso 1 1 d . . . H4B H 0.1835(9) 0.0178(3) 0.1863(18) 0.021(4) Uiso 1 1 d . . . H23C H -0.0658(12) 0.1275(4) 0.088(2) 0.034(5) Uiso 1 1 d . . . H7 H -0.0189(10) 0.1173(3) 0.3160(19) 0.027(4) Uiso 1 1 d . . . H3B H 0.0981(10) -0.0047(3) 0.3509(18) 0.022(4) Uiso 1 1 d . . . H4A H 0.2282(11) 0.0333(3) 0.3269(19) 0.025(4) Uiso 1 1 d . . . H14 H 0.3278(11) 0.1015(4) 0.885(2) 0.033(4) Uiso 1 1 d . . . H23B H 0.0084(12) 0.1461(4) 0.116(3) 0.046(5) Uiso 1 1 d . . . H23A H -0.0204(11) 0.1393(4) -0.045(2) 0.036(5) Uiso 1 1 d . . . H20 H 0.0760(12) -0.0644(5) 0.956(3) 0.050(5) Uiso 1 1 d . . . H18 H 0.1263(11) -0.0449(4) 0.513(2) 0.038(5) 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 F1A 0.0071(11) 0.0324(13) 0.0281(13) -0.0036(11) -0.0023(9) -0.0017(9) F1B 0.0465(7) 0.0363(7) 0.0360(7) -0.0091(6) 0.0086(6) -0.0048(6) F2A 0.0595(16) 0.0205(11) 0.0498(16) 0.0082(11) -0.0286(13) -0.0083(10) F2B 0.0403(8) 0.0417(8) 0.0309(7) 0.0083(6) 0.0037(6) 0.0024(6) O1 0.0315(5) 0.0328(5) 0.0251(5) 0.0014(4) -0.0018(4) 0.0063(4) N2 0.0259(6) 0.0210(6) 0.0287(6) 0.0005(5) 0.0025(5) 0.0018(4) C9 0.0229(6) 0.0216(6) 0.0268(7) 0.0001(5) 0.0020(5) -0.0009(5) C5 0.0229(6) 0.0264(6) 0.0228(7) -0.0027(5) 0.0026(5) -0.0011(5) C22 0.0202(6) 0.0267(7) 0.0366(8) 0.0058(6) -0.0019(6) 0.0010(5) C10 0.0218(6) 0.0218(6) 0.0270(7) -0.0037(5) 0.0029(5) -0.0021(5) C7 0.0212(6) 0.0227(6) 0.0311(7) -0.0008(6) 0.0006(5) 0.0016(5) C8 0.0251(7) 0.0256(6) 0.0264(7) -0.0015(6) 0.0061(5) 0.0014(5) C14 0.0570(10) 0.0282(7) 0.0267(8) 0.0043(6) -0.0088(7) -0.0107(7) C1 0.0242(6) 0.0221(6) 0.0266(7) 0.0024(5) 0.0068(6) 0.0033(5) C17 0.0154(6) 0.0259(7) 0.0333(8) 0.0042(6) -0.0033(6) -0.0005(5) C4 0.0271(7) 0.0282(7) 0.0277(7) -0.0030(6) 0.0042(6) 0.0049(6) C20 0.0289(8) 0.0360(8) 0.0460(9) 0.0176(7) -0.0132(7) -0.0083(6) C12 0.0347(7) 0.0226(6) 0.0247(6) 0.0004(6) 0.0012(6) -0.0008(5) C11 0.0362(8) 0.0190(6) 0.0214(6) 0.0046(5) 0.0028(6) 0.0003(5) C6 0.0210(6) 0.0258(6) 0.0253(7) -0.0008(6) -0.0021(5) -0.0027(5) C23 0.0363(9) 0.0430(10) 0.0326(9) 0.0094(7) 0.0014(7) 0.0133(7) C19 0.0308(8) 0.0291(7) 0.0504(10) 0.0104(7) -0.0164(7) -0.0071(6) C21 0.0209(6) 0.0399(8) 0.0367(9) 0.0121(7) -0.0046(6) -0.0009(6) C3 0.0316(8) 0.0229(7) 0.0301(7) -0.0052(6) 0.0030(6) 0.0053(6) C18 0.0271(7) 0.0252(7) 0.0407(9) 0.0036(6) -0.0109(6) -0.0015(5) C13 0.0531(11) 0.0279(7) 0.0282(7) 0.0059(6) -0.0048(7) -0.0087(7) C16 0.0467(9) 0.0234(6) 0.0229(7) 0.0029(5) 0.0059(6) 0.0046(6) C15 0.0724(12) 0.0199(7) 0.0217(7) 0.0003(6) -0.0009(7) -0.0056(7) _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 F1A C13 1.148(3) . ? F1B C15 1.327(2) . ? F2A C19 1.262(3) . ? F2B C21 1.296(2) . ? O1 C6 1.3688(17) . ? O1 C23 1.4249(19) . ? N2 C17 1.3854(18) . ? N2 C3 1.4631(18) . ? N2 C1 1.4688(17) . ? C9 C8 1.3938(19) . ? C9 C10 1.394(2) . ? C9 C1 1.518(2) . ? C5 C10 1.390(2) . ? C5 C6 1.390(2) . ? C5 H5 0.965(19) . ? C22 C21 1.379(2) . ? C22 C17 1.413(2) . ? C22 H31 1.030(16) . ? C10 C4 1.4997(19) . ? C7 C6 1.390(2) . ? C7 C8 1.392(2) . ? C7 H7 0.984(16) . ? C8 H8 0.956(17) . ? C14 C15 1.372(3) . ? C14 C13 1.385(2) . ? C14 H14 0.972(19) . ? C1 C11 1.534(2) . ? C1 H1 0.981(16) . ? C17 C18 1.412(2) . ? C4 C3 1.515(2) . ? C4 H4B 1.039(16) . ? C4 H4A 0.941(17) . ? C20 C19 1.376(3) . ? C20 C21 1.385(2) . ? C20 H20 1.01(2) . ? C12 C11 1.389(2) . ? C12 C13 1.391(2) . ? C12 H12 0.978(16) . ? C11 C16 1.397(2) . ? C23 H23C 0.94(2) . ? C23 H23B 0.98(2) . ? C23 H23A 0.93(2) . ? C19 C18 1.382(2) . ? C3 H3A 0.95(2) . ? C3 H3B 0.967(17) . ? C18 H18 1.02(2) . ? C16 C15 1.386(2) . ? C16 H16 0.969(17) . ? 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 C6 O1 C23 117.21(11) . . ? C17 N2 C3 118.23(11) . . ? C17 N2 C1 118.49(11) . . ? C3 N2 C1 120.92(11) . . ? C8 C9 C10 118.86(13) . . ? C8 C9 C1 119.83(12) . . ? C10 C9 C1 121.30(12) . . ? C10 C5 C6 120.61(13) . . ? C10 C5 H5 120.7(10) . . ? C6 C5 H5 118.7(10) . . ? C21 C22 C17 119.60(14) . . ? C21 C22 H31 119.2(9) . . ? C17 C22 H31 121.2(9) . . ? C5 C10 C9 120.05(12) . . ? C5 C10 C4 122.57(12) . . ? C9 C10 C4 117.38(12) . . ? C6 C7 C8 119.28(12) . . ? C6 C7 H7 119.9(10) . . ? C8 C7 H7 120.9(10) . . ? C7 C8 C9 121.29(13) . . ? C7 C8 H8 120.1(9) . . ? C9 C8 H8 118.5(9) . . ? C15 C14 C13 117.62(15) . . ? C15 C14 H14 118.8(11) . . ? C13 C14 H14 123.6(11) . . ? N2 C1 C9 112.87(12) . . ? N2 C1 C11 111.54(11) . . ? C9 C1 C11 111.16(11) . . ? N2 C1 H1 107.3(9) . . ? C9 C1 H1 107.1(9) . . ? C11 C1 H1 106.5(9) . . ? N2 C17 C18 121.19(13) . . ? N2 C17 C22 121.29(12) . . ? C18 C17 C22 117.51(13) . . ? C10 C4 C3 110.18(12) . . ? C10 C4 H4B 111.9(8) . . ? C3 C4 H4B 106.7(8) . . ? C10 C4 H4A 108.3(9) . . ? C3 C4 H4A 108.5(10) . . ? H4B C4 H4A 111.2(13) . . ? C19 C20 C21 116.46(14) . . ? C19 C20 H20 124.2(12) . . ? C21 C20 H20 119.3(12) . . ? C11 C12 C13 120.37(14) . . ? C11 C12 H12 118.2(10) . . ? C13 C12 H12 121.4(10) . . ? C12 C11 C16 118.69(14) . . ? C12 C11 C1 121.47(12) . . ? C16 C11 C1 119.84(13) . . ? O1 C6 C7 124.33(12) . . ? O1 C6 C5 115.82(12) . . ? C7 C6 C5 119.85(13) . . ? O1 C23 H23C 110.1(11) . . ? O1 C23 H23B 112.8(12) . . ? H23C C23 H23B 104.5(17) . . ? O1 C23 H23A 110.3(12) . . ? H23C C23 H23A 109.3(16) . . ? H23B C23 H23A 109.6(18) . . ? F2A C19 C20 114.65(19) . . ? F2A C19 C18 122.3(2) . . ? C20 C19 C18 123.00(15) . . ? F2B C21 C22 118.88(15) . . ? F2B C21 C20 117.78(15) . . ? C22 C21 C20 123.34(16) . . ? N2 C3 C4 112.26(11) . . ? N2 C3 H3A 107.0(12) . . ? C4 C3 H3A 109.9(11) . . ? N2 C3 H3B 108.5(9) . . ? C4 C3 H3B 107.8(9) . . ? H3A C3 H3B 111.4(14) . . ? C19 C18 C17 120.06(15) . . ? C19 C18 H18 119.8(11) . . ? C17 C18 H18 120.0(11) . . ? F1A C13 C14 116.42(19) . . ? F1A C13 C12 122.26(19) . . ? C14 C13 C12 121.27(17) . . ? C15 C16 C11 119.33(15) . . ? C15 C16 H16 119.9(10) . . ? C11 C16 H16 120.8(10) . . ? F1B C15 C14 113.61(15) . . ? F1B C15 C16 123.65(17) . . ? C14 C15 C16 122.71(14) . . ? 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 C6 C5 C10 C9 2.38(19) . . . . ? C6 C5 C10 C4 -178.39(13) . . . . ? C8 C9 C10 C5 -1.93(19) . . . . ? C1 C9 C10 C5 179.20(12) . . . . ? C8 C9 C10 C4 178.81(12) . . . . ? C1 C9 C10 C4 -0.07(19) . . . . ? C6 C7 C8 C9 2.0(2) . . . . ? C10 C9 C8 C7 -0.2(2) . . . . ? C1 C9 C8 C7 178.65(12) . . . . ? C17 N2 C1 C9 -151.23(11) . . . . ? C3 N2 C1 C9 11.02(17) . . . . ? C17 N2 C1 C11 82.78(14) . . . . ? C3 N2 C1 C11 -114.97(14) . . . . ? C8 C9 C1 N2 154.25(12) . . . . ? C10 C9 C1 N2 -26.89(17) . . . . ? C8 C9 C1 C11 -79.55(15) . . . . ? C10 C9 C1 C11 99.31(15) . . . . ? C3 N2 C17 C18 -0.43(18) . . . . ? C1 N2 C17 C18 162.29(12) . . . . ? C3 N2 C17 C22 178.97(12) . . . . ? C1 N2 C17 C22 -18.30(18) . . . . ? C21 C22 C17 N2 179.13(12) . . . . ? C21 C22 C17 C18 -1.45(18) . . . . ? C5 C10 C4 C3 -138.37(13) . . . . ? C9 C10 C4 C3 40.88(17) . . . . ? C13 C12 C11 C16 -0.3(2) . . . . ? C13 C12 C11 C1 179.86(13) . . . . ? N2 C1 C11 C12 30.55(18) . . . . ? C9 C1 C11 C12 -96.38(15) . . . . ? N2 C1 C11 C16 -149.29(12) . . . . ? C9 C1 C11 C16 83.78(16) . . . . ? C23 O1 C6 C7 6.3(2) . . . . ? C23 O1 C6 C5 -173.73(13) . . . . ? C8 C7 C6 O1 178.48(12) . . . . ? C8 C7 C6 C5 -1.50(19) . . . . ? C10 C5 C6 O1 179.37(11) . . . . ? C10 C5 C6 C7 -0.6(2) . . . . ? C21 C20 C19 F2A -179.39(17) . . . . ? C21 C20 C19 C18 -1.5(2) . . . . ? C17 C22 C21 F2B -179.92(13) . . . . ? C17 C22 C21 C20 0.7(2) . . . . ? C19 C20 C21 F2B -178.60(15) . . . . ? C19 C20 C21 C22 0.8(2) . . . . ? C17 N2 C3 C4 -168.81(12) . . . . ? C1 N2 C3 C4 28.90(18) . . . . ? C10 C4 C3 N2 -54.51(16) . . . . ? F2A C19 C18 C17 178.44(18) . . . . ? C20 C19 C18 C17 0.8(2) . . . . ? N2 C17 C18 C19 -179.79(13) . . . . ? C22 C17 C18 C19 0.78(19) . . . . ? C15 C14 C13 F1A -177.5(2) . . . . ? C15 C14 C13 C12 -0.1(2) . . . . ? C11 C12 C13 F1A 177.6(2) . . . . ? C11 C12 C13 C14 0.3(2) . . . . ? C12 C11 C16 C15 0.1(2) . . . . ? C1 C11 C16 C15 179.99(13) . . . . ? C13 C14 C15 F1B -178.28(13) . . . . ? C13 C14 C15 C16 -0.1(2) . . . . ? C11 C16 C15 F1B 178.07(14) . . . . ? C11 C16 C15 C14 0.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.212 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.037 # Attachment '1_new.cif' data_arc1n _database_code_depnum_ccdc_archive 'CCDC 290605' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H20 F N O' _chemical_formula_weight 333.39 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' N N 0.0061 0.0033 '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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 15.952(4) _cell_length_b 17.980(4) _cell_length_c 6.0391(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1732.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(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 ? _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 15607 _diffrn_reflns_av_R_equivalents 0.0623 _diffrn_reflns_av_sigmaI/netI 0.0555 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.13 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3053 _reflns_number_gt 2288 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.1424P)^2^+2.2338P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(4) _refine_ls_number_reflns 3053 _refine_ls_number_parameters 294 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1171 _refine_ls_R_factor_gt 0.0842 _refine_ls_wR_factor_ref 0.2455 _refine_ls_wR_factor_gt 0.2209 _refine_ls_goodness_of_fit_ref 0.982 _refine_ls_restrained_S_all 0.982 _refine_ls_shift/su_max 0.013 _refine_ls_shift/su_mean 0.003 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 C2 C 0.6405(4) 0.2527(4) 0.5606(10) 0.0424(14) Uani 1 1 d . . . C9 C 0.6419(3) 0.3829(3) 0.4071(9) 0.0356(13) Uani 1 1 d . . . N1 N 0.6398(3) 0.2289(3) 0.3284(7) 0.0359(11) Uani 1 1 d . . . C6 C 0.5771(4) 0.4829(3) 0.0982(11) 0.0440(14) Uani 1 1 d . . . C4 C 0.6546(3) 0.4592(4) 0.4262(11) 0.0418(14) Uani 1 1 d . . . C16 C 0.6316(3) 0.1515(3) 0.2907(11) 0.0419(14) Uani 1 1 d . . . O1 O 0.6317(3) 0.5850(2) 0.2890(8) 0.0545(12) Uani 1 1 d . . . C8 C 0.5970(3) 0.3563(3) 0.2253(9) 0.0332(12) Uani 1 1 d . . . C17 C 0.6646(4) 0.1218(4) 0.0963(11) 0.0481(16) Uani 1 1 d . . . C7 C 0.5644(3) 0.4075(3) 0.0719(10) 0.0390(14) Uani 1 1 d . . . C5 C 0.6227(3) 0.5091(3) 0.2794(11) 0.0406(14) Uani 1 1 d . . . F1 F 0.6160(4) -0.0724(2) 0.1566(10) 0.116(2) Uani 1 1 d . . . C1 C 0.5808(3) 0.2744(3) 0.1894(9) 0.0350(13) Uani 1 1 d . . . C11 C 0.4534(4) 0.1984(3) 0.0950(12) 0.0472(15) Uani 1 1 d . . . C19 C 0.6223(5) 0.0013(4) 0.2031(14) 0.071(2) Uani 1 1 d . . . C15 C 0.4425(4) 0.2812(3) 0.3984(11) 0.0432(14) Uani 1 1 d . . . C12 C 0.3728(4) 0.1741(4) 0.1340(14) 0.0580(19) Uani 1 1 d . . . C3 C 0.6786(4) 0.3302(4) 0.5714(10) 0.0425(14) Uani 1 1 d . . . C18 C 0.6597(5) 0.0461(4) 0.0467(14) 0.067(2) Uani 1 1 d . . . C20 C 0.5896(6) 0.0277(4) 0.3959(15) 0.072(2) Uani 1 1 d . . . C21 C 0.5949(4) 0.1020(4) 0.4376(13) 0.0558(17) Uani 1 1 d . . . C10 C 0.4901(3) 0.2527(3) 0.2278(10) 0.0359(12) Uani 1 1 d . . . C13 C 0.3281(4) 0.2030(4) 0.3056(16) 0.064(2) Uani 1 1 d . . . C14 C 0.3620(4) 0.2572(4) 0.4395(14) 0.0549(17) Uani 1 1 d . . . C22 C 0.6730(5) 0.6148(4) 0.4796(13) 0.069(2) Uani 1 1 d . . . H3A H 0.740(5) 0.323(3) 0.547(11) 0.052(17) Uiso 1 1 d . . . H15 H 0.462(3) 0.315(3) 0.484(9) 0.021(13) Uiso 1 1 d . . . H11 H 0.487(4) 0.173(3) -0.019(11) 0.052(18) Uiso 1 1 d . . . H1 H 0.597(3) 0.260(3) 0.047(10) 0.020(12) Uiso 1 1 d . . . H2B H 0.584(4) 0.253(3) 0.617(9) 0.030(13) Uiso 1 1 d . . . H3B H 0.669(5) 0.338(4) 0.712(15) 0.07(2) Uiso 1 1 d . . . H6 H 0.561(3) 0.518(3) 0.002(9) 0.023(13) Uiso 1 1 d . . . H21 H 0.570(3) 0.123(3) 0.567(9) 0.029(13) Uiso 1 1 d . . . H13 H 0.272(5) 0.189(4) 0.324(16) 0.10(3) Uiso 1 1 d . . . H4 H 0.687(4) 0.472(3) 0.551(12) 0.049(17) Uiso 1 1 d . . . H2A H 0.679(3) 0.216(3) 0.634(10) 0.038(14) Uiso 1 1 d . . . H17 H 0.694(4) 0.157(3) -0.013(12) 0.052(18) Uiso 1 1 d . . . H14 H 0.329(4) 0.283(4) 0.569(13) 0.064(19) Uiso 1 1 d . . . H18 H 0.688(4) 0.030(4) -0.071(17) 0.08(2) Uiso 1 1 d . . . H7 H 0.526(4) 0.386(3) -0.031(13) 0.07(2) Uiso 1 1 d . . . H20 H 0.562(5) -0.002(5) 0.492(16) 0.09(3) Uiso 1 1 d . . . H12 H 0.350(3) 0.134(3) 0.056(11) 0.045(17) 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 C2 0.037(3) 0.061(4) 0.029(3) 0.005(3) -0.002(3) 0.009(3) C9 0.024(2) 0.053(4) 0.029(3) -0.001(3) 0.002(2) 0.004(2) N1 0.034(2) 0.048(3) 0.026(2) -0.002(2) 0.000(2) 0.005(2) C6 0.047(3) 0.045(4) 0.040(3) 0.007(3) -0.003(3) 0.002(3) C4 0.033(3) 0.061(4) 0.031(3) -0.011(3) -0.007(3) -0.003(3) C16 0.038(3) 0.051(4) 0.037(3) 0.002(3) -0.002(3) 0.008(3) O1 0.066(3) 0.043(3) 0.055(3) -0.002(2) 0.001(2) -0.009(2) C8 0.023(2) 0.050(3) 0.026(3) 0.003(3) 0.005(2) 0.002(2) C17 0.050(3) 0.053(4) 0.042(4) 0.003(3) -0.004(3) 0.013(3) C7 0.028(3) 0.054(4) 0.035(3) 0.006(3) -0.002(3) 0.000(2) C5 0.035(3) 0.049(4) 0.038(3) -0.001(3) 0.003(2) -0.004(3) F1 0.200(6) 0.049(3) 0.098(4) -0.009(3) -0.005(4) 0.006(3) C1 0.036(3) 0.050(3) 0.019(3) -0.003(2) 0.000(2) 0.009(2) C11 0.045(3) 0.041(3) 0.055(4) -0.006(3) -0.003(3) 0.012(3) C19 0.098(6) 0.047(4) 0.068(5) 0.000(4) -0.023(5) 0.014(4) C15 0.045(3) 0.044(3) 0.040(4) -0.001(3) -0.005(3) -0.001(3) C12 0.047(4) 0.045(4) 0.082(5) 0.002(4) -0.018(4) -0.002(3) C3 0.037(3) 0.064(4) 0.027(3) -0.007(3) -0.003(3) 0.003(3) C18 0.091(6) 0.062(5) 0.047(4) -0.003(4) -0.003(4) 0.028(4) C20 0.087(6) 0.058(5) 0.071(6) 0.012(5) -0.004(5) -0.004(4) C21 0.071(4) 0.045(4) 0.051(4) -0.003(3) 0.017(4) 0.004(3) C10 0.041(3) 0.037(3) 0.030(2) -0.001(2) 0.002(3) 0.010(2) C13 0.042(4) 0.061(4) 0.090(6) 0.019(4) 0.004(4) -0.002(3) C14 0.047(4) 0.061(4) 0.057(4) 0.014(4) 0.010(4) 0.008(3) C22 0.084(5) 0.053(4) 0.070(5) -0.013(4) -0.013(4) -0.010(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 C2 N1 1.466(7) . ? C2 C3 1.521(9) . ? C9 C8 1.396(8) . ? C9 C4 1.391(8) . ? C9 C3 1.492(9) . ? N1 C16 1.416(8) . ? N1 C1 1.502(6) . ? C6 C7 1.381(8) . ? C6 C5 1.396(8) . ? C4 C5 1.360(9) . ? C16 C21 1.387(9) . ? C16 C17 1.393(9) . ? O1 C5 1.372(7) . ? O1 C22 1.431(9) . ? C8 C7 1.405(8) . ? C8 C1 1.511(8) . ? C17 C18 1.396(10) . ? F1 C19 1.358(9) . ? C1 C10 1.517(7) . ? C11 C10 1.392(8) . ? C11 C12 1.377(9) . ? C19 C20 1.362(12) . ? C19 C18 1.377(12) . ? C15 C14 1.378(9) . ? C15 C10 1.379(8) . ? C12 C13 1.362(11) . ? C20 C21 1.362(10) . ? C13 C14 1.377(11) . ? 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 N1 C2 C3 108.1(5) . . ? C8 C9 C4 118.6(5) . . ? C8 C9 C3 120.4(5) . . ? C4 C9 C3 121.0(5) . . ? C16 N1 C2 116.1(5) . . ? C16 N1 C1 112.8(4) . . ? C2 N1 C1 112.4(5) . . ? C7 C6 C5 119.9(6) . . ? C9 C4 C5 122.8(5) . . ? C21 C16 C17 116.9(6) . . ? C21 C16 N1 124.5(6) . . ? C17 C16 N1 118.6(6) . . ? C5 O1 C22 117.0(5) . . ? C9 C8 C7 118.9(5) . . ? C9 C8 C1 122.4(5) . . ? C7 C8 C1 118.7(5) . . ? C18 C17 C16 122.3(7) . . ? C6 C7 C8 120.9(6) . . ? O1 C5 C4 126.1(6) . . ? O1 C5 C6 115.0(5) . . ? C4 C5 C6 118.9(6) . . ? N1 C1 C8 110.1(4) . . ? N1 C1 C10 111.8(5) . . ? C8 C1 C10 113.0(4) . . ? C10 C11 C12 121.1(6) . . ? C20 C19 F1 119.2(8) . . ? C20 C19 C18 123.3(7) . . ? F1 C19 C18 117.5(8) . . ? C14 C15 C10 122.0(7) . . ? C13 C12 C11 119.8(7) . . ? C9 C3 C2 113.4(5) . . ? C19 C18 C17 116.6(8) . . ? C19 C20 C21 118.4(8) . . ? C20 C21 C16 122.5(7) . . ? C11 C10 C15 117.4(5) . . ? C11 C10 C1 119.6(5) . . ? C15 C10 C1 122.9(5) . . ? C12 C13 C14 120.8(7) . . ? C13 C14 C15 118.9(7) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.316 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.056 # Attachment '2.cif' data_arc2 _database_code_depnum_ccdc_archive 'CCDC 290606' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H20 F N O' _chemical_formula_weight 333.39 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' N N 0.0061 0.0033 '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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.1076(11) _cell_length_b 9.1597(6) _cell_length_c 23.6002(16) _cell_angle_alpha 90.00 _cell_angle_beta 107.1160(10) _cell_angle_gamma 90.00 _cell_volume 3327.8(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9570 _exptl_absorpt_correction_T_max 0.9612 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _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 20606 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 26.36 _reflns_number_total 3403 _reflns_number_gt 3126 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0436P)^2^+2.9903P] 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 3403 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1004 _refine_ls_wR_factor_gt 0.0980 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 0.70246(9) 0.45093(15) 0.43191(5) 0.0325(3) Uani 0.67 1 d P . . F2 F 0.58634(17) 0.7884(3) 0.28345(12) 0.0306(6) Uani 0.33 1 d P . . O1 O 0.44032(6) -0.18796(10) 0.04051(4) 0.0226(2) Uani 1 1 d . . . N2 N 0.62331(7) 0.29887(12) 0.23089(5) 0.0179(2) Uani 1 1 d . . . C22 C 0.60535(8) 0.55220(15) 0.25679(6) 0.0198(3) Uani 1 1 d . . . C1 C 0.56845(8) 0.32755(14) 0.17028(5) 0.0161(3) Uani 1 1 d . . . C18 C 0.66467(9) 0.37643(16) 0.33373(6) 0.0215(3) Uani 1 1 d . . . C9 C 0.53275(8) 0.18925(14) 0.13621(5) 0.0162(3) Uani 1 1 d . . . C11 C 0.61628(8) 0.41858(14) 0.13531(6) 0.0164(3) Uani 1 1 d . . . C8 C 0.45931(8) 0.19649(15) 0.08733(6) 0.0173(3) Uani 1 1 d . . . C5 C 0.54104(9) -0.06855(15) 0.11829(6) 0.0193(3) Uani 1 1 d . . . C6 C 0.46760(8) -0.05964(14) 0.06933(6) 0.0182(3) Uani 1 1 d . . . C3 C 0.64720(9) 0.15021(15) 0.25158(6) 0.0217(3) Uani 1 1 d . . . C10 C 0.57423(8) 0.05509(15) 0.15085(6) 0.0177(3) Uani 1 1 d . . . C13 C 0.74681(9) 0.48411(16) 0.11094(6) 0.0213(3) Uani 1 1 d . . . C17 C 0.63084(8) 0.40731(15) 0.27290(6) 0.0179(3) Uani 1 1 d . . . C15 C 0.61145(10) 0.59567(15) 0.05862(6) 0.0234(3) Uani 1 1 d . . . C7 C 0.42696(8) 0.07434(15) 0.05331(6) 0.0178(3) Uani 1 1 d . . . C19 C 0.67032(9) 0.48620(17) 0.37464(6) 0.0258(3) Uani 1 1 d . . . C20 C 0.64341(9) 0.62710(18) 0.35978(7) 0.0273(3) Uani 1 1 d . . . C16 C 0.56999(9) 0.51563(15) 0.09225(6) 0.0203(3) Uani 1 1 d . . . C4 C 0.65520(9) 0.05118(15) 0.20221(6) 0.0211(3) Uani 1 1 d . . . C14 C 0.70005(9) 0.57947(15) 0.06775(6) 0.0230(3) Uani 1 1 d . . . C12 C 0.70527(8) 0.40444(15) 0.14471(6) 0.0183(3) Uani 1 1 d . . . C21 C 0.61117(9) 0.65724(16) 0.29979(6) 0.0241(3) Uani 1 1 d . . . C23 C 0.36706(9) -0.18252(16) -0.01109(6) 0.0236(3) Uani 1 1 d . . . H1 H 0.5169(9) 0.3866(15) 0.1722(6) 0.010(3) Uiso 1 1 d . . . H4A H 0.7061(10) 0.0841(17) 0.1889(7) 0.022(4) Uiso 1 1 d . . . H13 H 0.8090(11) 0.4740(18) 0.1178(7) 0.027(4) Uiso 1 1 d . . . H12 H 0.7388(10) 0.3371(17) 0.1752(7) 0.022(4) Uiso 1 1 d . . . H18 H 0.6838(10) 0.2791(19) 0.3487(7) 0.024(4) Uiso 1 1 d . . . H8 H 0.4289(10) 0.2901(17) 0.0762(6) 0.018(4) Uiso 1 1 d . . . H5 H 0.5699(10) -0.1630(18) 0.1294(7) 0.023(4) Uiso 1 1 d . . . H22 H 0.5829(10) 0.5806(17) 0.2154(7) 0.019(4) Uiso 1 1 d . . . H7 H 0.3759(10) 0.0835(16) 0.0194(7) 0.018(4) Uiso 1 1 d . . . H4B H 0.6676(10) -0.0488(18) 0.2176(7) 0.022(4) Uiso 1 1 d . . . H3B H 0.6036(10) 0.1087(17) 0.2698(7) 0.022(4) Uiso 1 1 d . . . H20 H 0.6455(11) 0.7008(19) 0.3900(8) 0.031(4) Uiso 1 1 d . . . H16 H 0.5076(10) 0.5297(18) 0.0864(7) 0.023(4) Uiso 1 1 d . . . H15 H 0.5772(10) 0.6633(18) 0.0292(7) 0.026(4) Uiso 1 1 d . . . H23A H 0.3142(11) -0.1493(19) -0.0021(7) 0.031(4) Uiso 1 1 d . . . H3A H 0.7045(10) 0.1536(17) 0.2827(7) 0.023(4) Uiso 1 1 d . . . H14 H 0.7290(10) 0.6355(18) 0.0441(7) 0.024(4) Uiso 1 1 d . . . H23B H 0.3588(10) -0.2846(19) -0.0256(7) 0.025(4) Uiso 1 1 d . . . H23C H 0.3789(10) -0.1174(18) -0.0421(7) 0.027(4) 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 F1 0.0445(8) 0.0393(8) 0.0133(6) -0.0054(5) 0.0080(5) -0.0203(6) F2 0.0280(13) 0.0298(14) 0.0328(14) -0.0087(11) 0.0073(11) -0.0001(11) O1 0.0241(5) 0.0183(5) 0.0234(5) -0.0025(4) 0.0038(4) -0.0028(4) N2 0.0188(5) 0.0195(6) 0.0147(5) -0.0001(4) 0.0040(4) 0.0014(4) C22 0.0140(6) 0.0258(7) 0.0196(7) -0.0030(6) 0.0049(5) -0.0014(5) C1 0.0143(6) 0.0185(6) 0.0155(6) -0.0003(5) 0.0042(5) 0.0020(5) C18 0.0208(7) 0.0261(8) 0.0189(7) -0.0001(6) 0.0078(5) -0.0065(6) C9 0.0157(6) 0.0188(6) 0.0159(6) 0.0003(5) 0.0077(5) -0.0002(5) C11 0.0187(6) 0.0143(6) 0.0164(6) -0.0043(5) 0.0055(5) -0.0009(5) C8 0.0160(6) 0.0193(7) 0.0183(6) 0.0019(5) 0.0074(5) 0.0023(5) C5 0.0207(6) 0.0178(7) 0.0204(7) 0.0020(5) 0.0076(5) 0.0020(5) C6 0.0196(6) 0.0188(7) 0.0185(6) -0.0015(5) 0.0094(5) -0.0037(5) C3 0.0229(7) 0.0219(7) 0.0177(6) 0.0029(5) 0.0022(5) 0.0018(5) C10 0.0168(6) 0.0210(7) 0.0170(6) 0.0013(5) 0.0076(5) 0.0001(5) C13 0.0197(7) 0.0235(7) 0.0225(7) -0.0059(5) 0.0089(5) -0.0040(5) C17 0.0122(6) 0.0243(7) 0.0187(6) -0.0028(5) 0.0069(5) -0.0038(5) C15 0.0311(7) 0.0188(7) 0.0202(7) 0.0015(6) 0.0076(6) 0.0019(6) C7 0.0145(6) 0.0227(7) 0.0166(6) 0.0002(5) 0.0054(5) -0.0015(5) C19 0.0243(7) 0.0355(8) 0.0192(7) -0.0036(6) 0.0087(6) -0.0138(6) C20 0.0259(7) 0.0337(8) 0.0258(7) -0.0128(6) 0.0131(6) -0.0122(6) C16 0.0198(6) 0.0191(7) 0.0217(7) -0.0011(5) 0.0057(5) 0.0012(5) C4 0.0201(6) 0.0186(7) 0.0226(7) 0.0014(5) 0.0030(5) 0.0032(5) C14 0.0306(7) 0.0211(7) 0.0204(7) -0.0026(5) 0.0124(6) -0.0056(6) C12 0.0186(6) 0.0188(6) 0.0171(6) -0.0026(5) 0.0047(5) 0.0002(5) C21 0.0182(6) 0.0252(7) 0.0309(8) -0.0085(6) 0.0104(6) -0.0047(5) C23 0.0240(7) 0.0240(8) 0.0218(7) -0.0043(6) 0.0051(6) -0.0036(6) _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 C19 1.3367(19) . ? F2 C21 1.289(3) . ? O1 C6 1.3643(16) . ? O1 C23 1.4255(17) . ? N2 C17 1.3834(17) . ? N2 C3 1.4595(17) . ? N2 C1 1.4670(16) . ? C22 C21 1.3815(19) . ? C22 C17 1.408(2) . ? C22 H22 0.973(16) . ? C1 C9 1.5198(18) . ? C1 C11 1.5311(17) . ? C1 H1 1.003(14) . ? C18 C19 1.378(2) . ? C18 C17 1.4062(19) . ? C18 H18 0.975(17) . ? C9 C8 1.3897(18) . ? C9 C10 1.3928(18) . ? C11 C16 1.3904(19) . ? C11 C12 1.3905(18) . ? C8 C7 1.3863(19) . ? C8 H8 0.984(15) . ? C5 C10 1.3847(19) . ? C5 C6 1.3915(19) . ? C5 H5 0.981(16) . ? C6 C7 1.3900(19) . ? C3 C4 1.5117(19) . ? C3 H3B 1.000(16) . ? C3 H3A 0.996(16) . ? C10 C4 1.4970(18) . ? C13 C14 1.385(2) . ? C13 C12 1.3890(19) . ? C13 H13 0.971(17) . ? C15 C14 1.387(2) . ? C15 C16 1.388(2) . ? C15 H15 0.972(17) . ? C7 H7 0.968(15) . ? C19 C20 1.374(2) . ? C20 C21 1.385(2) . ? C20 H20 0.976(18) . ? C16 H16 0.982(16) . ? C4 H4A 1.007(16) . ? C4 H4B 0.984(16) . ? C14 H14 0.972(17) . ? C12 H12 0.980(16) . ? C23 H23A 0.984(18) . ? C23 H23B 0.992(17) . ? C23 H23C 1.005(17) . ? 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 C6 O1 C23 117.39(11) . . ? C17 N2 C3 118.11(11) . . ? C17 N2 C1 118.09(11) . . ? C3 N2 C1 121.14(10) . . ? C21 C22 C17 120.44(13) . . ? C21 C22 H22 118.5(9) . . ? C17 C22 H22 121.1(9) . . ? N2 C1 C9 113.09(10) . . ? N2 C1 C11 111.64(10) . . ? C9 C1 C11 109.93(10) . . ? N2 C1 H1 108.8(8) . . ? C9 C1 H1 106.5(8) . . ? C11 C1 H1 106.6(8) . . ? C19 C18 C17 119.62(14) . . ? C19 C18 H18 117.6(9) . . ? C17 C18 H18 122.7(9) . . ? C8 C9 C10 118.49(12) . . ? C8 C9 C1 119.76(11) . . ? C10 C9 C1 121.67(11) . . ? C16 C11 C12 118.82(12) . . ? C16 C11 C1 119.70(11) . . ? C12 C11 C1 121.46(11) . . ? C7 C8 C9 121.69(12) . . ? C7 C8 H8 118.4(9) . . ? C9 C8 H8 119.9(9) . . ? C10 C5 C6 120.52(12) . . ? C10 C5 H5 119.9(9) . . ? C6 C5 H5 119.6(9) . . ? O1 C6 C7 124.62(12) . . ? O1 C6 C5 115.71(12) . . ? C7 C6 C5 119.66(12) . . ? N2 C3 C4 112.07(11) . . ? N2 C3 H3B 110.4(9) . . ? C4 C3 H3B 109.5(9) . . ? N2 C3 H3A 108.2(9) . . ? C4 C3 H3A 108.5(9) . . ? H3B C3 H3A 108.0(13) . . ? C5 C10 C9 120.35(12) . . ? C5 C10 C4 122.14(12) . . ? C9 C10 C4 117.52(12) . . ? C14 C13 C12 120.28(13) . . ? C14 C13 H13 119.6(10) . . ? C12 C13 H13 120.1(10) . . ? N2 C17 C18 120.88(12) . . ? N2 C17 C22 121.74(12) . . ? C18 C17 C22 117.38(12) . . ? C14 C15 C16 120.06(13) . . ? C14 C15 H15 121.4(10) . . ? C16 C15 H15 118.5(10) . . ? C8 C7 C6 119.23(12) . . ? C8 C7 H7 119.5(9) . . ? C6 C7 H7 121.3(9) . . ? F1 C19 C20 118.98(14) . . ? F1 C19 C18 117.26(15) . . ? C20 C19 C18 123.75(14) . . ? C19 C20 C21 116.34(13) . . ? C19 C20 H20 121.5(10) . . ? C21 C20 H20 122.1(10) . . ? C15 C16 C11 120.73(12) . . ? C15 C16 H16 119.8(9) . . ? C11 C16 H16 119.5(9) . . ? C10 C4 C3 110.98(11) . . ? C10 C4 H4A 109.6(9) . . ? C3 C4 H4A 108.8(9) . . ? C10 C4 H4B 110.8(9) . . ? C3 C4 H4B 109.2(9) . . ? H4A C4 H4B 107.3(13) . . ? C13 C14 C15 119.59(13) . . ? C13 C14 H14 120.4(9) . . ? C15 C14 H14 120.0(9) . . ? C13 C12 C11 120.50(13) . . ? C13 C12 H12 119.8(9) . . ? C11 C12 H12 119.7(9) . . ? F2 C21 C22 118.77(17) . . ? F2 C21 C20 118.81(17) . . ? C22 C21 C20 122.42(14) . . ? O1 C23 H23A 112.2(10) . . ? O1 C23 H23B 104.8(9) . . ? H23A C23 H23B 109.2(14) . . ? O1 C23 H23C 110.8(9) . . ? H23A C23 H23C 109.6(14) . . ? H23B C23 H23C 110.1(13) . . ? 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 C17 N2 C1 C9 -154.54(11) . . . . ? C3 N2 C1 C9 6.65(16) . . . . ? C17 N2 C1 C11 80.87(13) . . . . ? C3 N2 C1 C11 -117.94(12) . . . . ? N2 C1 C9 C8 158.83(11) . . . . ? C11 C1 C9 C8 -75.65(14) . . . . ? N2 C1 C9 C10 -24.39(16) . . . . ? C11 C1 C9 C10 101.13(13) . . . . ? N2 C1 C11 C16 -147.92(12) . . . . ? C9 C1 C11 C16 85.74(14) . . . . ? N2 C1 C11 C12 33.44(16) . . . . ? C9 C1 C11 C12 -92.90(14) . . . . ? C10 C9 C8 C7 0.02(18) . . . . ? C1 C9 C8 C7 176.90(11) . . . . ? C23 O1 C6 C7 2.71(18) . . . . ? C23 O1 C6 C5 -177.88(11) . . . . ? C10 C5 C6 O1 -179.89(11) . . . . ? C10 C5 C6 C7 -0.45(19) . . . . ? C17 N2 C3 C4 -167.12(11) . . . . ? C1 N2 C3 C4 31.69(16) . . . . ? C6 C5 C10 C9 2.19(19) . . . . ? C6 C5 C10 C4 -177.37(12) . . . . ? C8 C9 C10 C5 -1.95(18) . . . . ? C1 C9 C10 C5 -178.77(11) . . . . ? C8 C9 C10 C4 177.62(11) . . . . ? C1 C9 C10 C4 0.80(18) . . . . ? C3 N2 C17 C18 3.14(17) . . . . ? C1 N2 C17 C18 164.91(11) . . . . ? C3 N2 C17 C22 -176.98(11) . . . . ? C1 N2 C17 C22 -15.21(17) . . . . ? C19 C18 C17 N2 -179.12(12) . . . . ? C19 C18 C17 C22 0.99(18) . . . . ? C21 C22 C17 N2 178.02(11) . . . . ? C21 C22 C17 C18 -2.09(18) . . . . ? C9 C8 C7 C6 1.69(19) . . . . ? O1 C6 C7 C8 177.93(11) . . . . ? C5 C6 C7 C8 -1.46(19) . . . . ? C17 C18 C19 F1 179.61(12) . . . . ? C17 C18 C19 C20 0.9(2) . . . . ? F1 C19 C20 C21 179.67(13) . . . . ? C18 C19 C20 C21 -1.7(2) . . . . ? C14 C15 C16 C11 0.0(2) . . . . ? C12 C11 C16 C15 0.86(19) . . . . ? C1 C11 C16 C15 -177.82(12) . . . . ? C5 C10 C4 C3 -141.83(13) . . . . ? C9 C10 C4 C3 38.61(16) . . . . ? N2 C3 C4 C10 -53.98(15) . . . . ? C12 C13 C14 C15 0.4(2) . . . . ? C16 C15 C14 C13 -0.6(2) . . . . ? C14 C13 C12 C11 0.5(2) . . . . ? C16 C11 C12 C13 -1.08(19) . . . . ? C1 C11 C12 C13 177.57(12) . . . . ? C17 C22 C21 F2 -179.22(17) . . . . ? C17 C22 C21 C20 1.4(2) . . . . ? C19 C20 C21 F2 -178.90(17) . . . . ? C19 C20 C21 C22 0.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.233 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.045 # Attachment '3.cif' data_arc3o _database_code_depnum_ccdc_archive 'CCDC 290607' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H20 F N O' _chemical_formula_weight 333.39 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' N N 0.0061 0.0033 '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 ? _symmetry_space_group_name_H-M ? 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' '-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 13.233(4) _cell_length_b 11.129(3) _cell_length_c 23.205(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3417.2(18) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9663 _exptl_absorpt_correction_T_max 0.9914 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _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 17193 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_sigmaI/netI 0.0352 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 26.39 _reflns_number_total 3432 _reflns_number_gt 2993 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0396P)^2^+1.4708P] 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 3432 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0947 _refine_ls_wR_factor_gt 0.0902 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 0.64712(6) 0.11360(7) 0.34613(4) 0.0280(2) Uani 1 1 d . . . O1 O 0.91179(7) 0.27849(8) 0.05958(4) 0.0235(2) Uani 1 1 d . . . C5 C 0.90384(9) 0.13174(12) 0.13257(5) 0.0174(3) Uani 1 1 d . . . N2 N 0.81916(8) 0.01880(9) 0.29797(4) 0.0162(2) Uani 1 1 d . . . C10 C 0.88935(9) 0.09554(11) 0.18954(5) 0.0159(3) Uani 1 1 d . . . C9 C 0.86673(9) 0.18248(11) 0.23153(5) 0.0150(3) Uani 1 1 d . . . C6 C 0.89559(9) 0.25277(12) 0.11693(5) 0.0173(3) Uani 1 1 d . . . C11 C 0.94588(9) 0.17454(11) 0.33053(5) 0.0152(3) Uani 1 1 d . . . C8 C 0.85840(9) 0.30308(12) 0.21532(5) 0.0171(3) Uani 1 1 d . . . C18 C 0.70174(10) 0.03389(12) 0.37847(6) 0.0217(3) Uani 1 1 d . . . C16 C 1.04394(9) 0.15303(11) 0.31041(5) 0.0161(3) Uani 1 1 d . . . C7 C 0.87190(9) 0.33937(12) 0.15836(5) 0.0176(3) Uani 1 1 d . . . C4 C 0.89234(10) -0.03737(11) 0.20455(6) 0.0186(3) Uani 1 1 d . . . C1 C 0.85199(9) 0.14780(11) 0.29407(5) 0.0152(3) Uani 1 1 d . . . C15 C 1.12696(10) 0.17428(11) 0.34584(6) 0.0188(3) Uani 1 1 d . . . C14 C 1.11358(10) 0.21993(12) 0.40120(6) 0.0215(3) Uani 1 1 d . . . C22 C 0.84022(10) -0.10134(12) 0.38822(6) 0.0214(3) Uani 1 1 d . . . C12 C 0.93366(10) 0.22093(12) 0.38602(5) 0.0193(3) Uani 1 1 d . . . C17 C 0.78903(9) -0.01609(11) 0.35435(5) 0.0178(3) Uani 1 1 d . . . C13 C 1.01706(10) 0.24442(13) 0.42116(6) 0.0227(3) Uani 1 1 d . . . C3 C 0.89043(10) -0.06361(11) 0.26911(5) 0.0176(3) Uani 1 1 d . . . C19 C 0.66750(11) 0.00637(13) 0.43308(6) 0.0269(3) Uani 1 1 d . . . C23 C 0.89438(13) 0.40078(14) 0.04185(6) 0.0292(3) Uani 1 1 d . . . C21 C 0.80559(11) -0.13223(13) 0.44291(6) 0.0261(3) Uani 1 1 d . . . C20 C 0.71997(11) -0.07825(14) 0.46585(6) 0.0285(3) Uani 1 1 d . . . H1 H 0.7972(10) 0.1952(12) 0.3093(5) 0.011(3) Uiso 1 1 d . . . H3A H 0.9591(11) -0.0577(13) 0.2852(6) 0.015(3) Uiso 1 1 d . . . H15 H 1.1939(11) 0.1592(13) 0.3313(6) 0.017(3) Uiso 1 1 d . . . H16 H 1.0558(11) 0.1269(13) 0.2710(6) 0.018(4) Uiso 1 1 d . . . H4A H 0.9531(12) -0.0744(14) 0.1875(6) 0.024(4) Uiso 1 1 d . . . H4B H 0.8328(12) -0.0752(14) 0.1867(6) 0.024(4) Uiso 1 1 d . . . H5 H 0.9189(11) 0.0717(14) 0.1032(6) 0.024(4) Uiso 1 1 d . . . H7 H 0.8650(11) 0.4236(14) 0.1481(6) 0.019(4) Uiso 1 1 d . . . H23B H 0.9449(12) 0.4555(16) 0.0605(7) 0.031(4) Uiso 1 1 d . . . H12 H 0.8671(12) 0.2369(13) 0.3999(6) 0.021(4) Uiso 1 1 d . . . H3B H 0.8661(11) -0.1492(14) 0.2762(6) 0.020(4) Uiso 1 1 d . . . H22 H 0.9009(12) -0.1373(13) 0.3731(6) 0.022(4) Uiso 1 1 d . . . H13 H 1.0057(12) 0.2772(14) 0.4603(7) 0.027(4) Uiso 1 1 d . . . H14 H 1.1731(11) 0.2355(13) 0.4252(6) 0.020(4) Uiso 1 1 d . . . H8 H 0.8422(11) 0.3637(14) 0.2446(6) 0.023(4) Uiso 1 1 d . . . H23A H 0.8259(13) 0.4251(15) 0.0520(7) 0.029(4) Uiso 1 1 d . . . H23C H 0.9032(12) 0.3994(15) -0.0008(8) 0.036(5) Uiso 1 1 d . . . H19 H 0.6046(13) 0.0439(16) 0.4462(7) 0.035(5) Uiso 1 1 d . . . H20 H 0.6932(13) -0.1001(15) 0.5051(7) 0.037(4) Uiso 1 1 d . . . H21 H 0.8446(13) -0.1935(15) 0.4656(7) 0.032(4) 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 F1 0.0184(4) 0.0304(5) 0.0353(5) 0.0041(4) 0.0046(3) 0.0049(3) O1 0.0315(5) 0.0202(5) 0.0188(5) 0.0026(4) 0.0018(4) 0.0014(4) C5 0.0144(6) 0.0172(7) 0.0206(6) -0.0032(5) -0.0002(5) 0.0012(5) N2 0.0154(5) 0.0135(5) 0.0196(5) 0.0001(4) 0.0014(4) -0.0005(4) C10 0.0100(6) 0.0160(6) 0.0217(6) -0.0016(5) -0.0018(5) 0.0003(5) C9 0.0104(6) 0.0151(6) 0.0194(6) -0.0011(5) -0.0029(4) -0.0008(5) C6 0.0136(6) 0.0198(7) 0.0186(6) 0.0010(5) -0.0021(5) -0.0008(5) C11 0.0161(6) 0.0099(6) 0.0195(6) 0.0020(4) -0.0007(5) -0.0004(5) C8 0.0142(6) 0.0156(6) 0.0214(6) -0.0026(5) -0.0021(5) -0.0005(5) C18 0.0185(6) 0.0204(7) 0.0263(7) 0.0000(5) -0.0008(5) -0.0037(5) C16 0.0185(6) 0.0112(6) 0.0187(6) 0.0012(5) 0.0017(5) -0.0003(5) C7 0.0166(6) 0.0132(6) 0.0229(6) 0.0006(5) -0.0034(5) -0.0010(5) C4 0.0188(7) 0.0140(6) 0.0230(7) -0.0025(5) 0.0012(5) 0.0004(5) C1 0.0126(6) 0.0130(6) 0.0201(6) -0.0013(5) 0.0012(5) 0.0011(5) C15 0.0155(6) 0.0144(6) 0.0265(7) 0.0059(5) 0.0007(5) 0.0000(5) C14 0.0209(7) 0.0215(7) 0.0220(6) 0.0058(5) -0.0059(5) -0.0053(5) C22 0.0202(7) 0.0201(7) 0.0241(7) -0.0005(5) -0.0026(5) -0.0040(5) C12 0.0171(6) 0.0195(7) 0.0213(6) -0.0005(5) 0.0032(5) -0.0012(5) C17 0.0168(6) 0.0164(6) 0.0200(6) -0.0009(5) -0.0010(5) -0.0060(5) C13 0.0260(7) 0.0243(7) 0.0178(6) -0.0010(5) 0.0000(5) -0.0046(6) C3 0.0164(6) 0.0129(6) 0.0234(6) 0.0004(5) 0.0000(5) 0.0007(5) C19 0.0233(7) 0.0284(8) 0.0290(7) -0.0059(6) 0.0060(6) -0.0090(6) C23 0.0393(9) 0.0243(8) 0.0242(7) 0.0065(6) 0.0035(6) 0.0062(7) C21 0.0315(8) 0.0237(8) 0.0230(7) 0.0024(5) -0.0054(6) -0.0087(6) C20 0.0335(8) 0.0308(8) 0.0212(7) -0.0012(6) 0.0012(6) -0.0155(6) _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 C18 1.3683(16) . ? O1 C6 1.3780(15) . ? O1 C23 1.4403(17) . ? C5 C10 1.3952(18) . ? C5 C6 1.3992(18) . ? C5 H5 0.976(15) . ? N2 C17 1.4216(16) . ? N2 C3 1.4761(16) . ? N2 C1 1.5026(16) . ? C10 C9 1.4054(17) . ? C10 C4 1.5201(18) . ? C9 C8 1.3983(18) . ? C9 C1 1.5141(17) . ? C6 C7 1.3970(18) . ? C11 C12 1.3967(18) . ? C11 C16 1.3997(18) . ? C11 C1 1.5323(17) . ? C8 C7 1.3935(18) . ? C8 H8 0.980(15) . ? C18 C19 1.3801(19) . ? C18 C17 1.3990(19) . ? C16 C15 1.3924(18) . ? C16 H16 0.973(14) . ? C7 H7 0.971(16) . ? C4 C3 1.5266(18) . ? C4 H4A 0.986(16) . ? C4 H4B 0.984(16) . ? C1 H1 0.965(14) . ? C15 C14 1.3927(19) . ? C15 H15 0.962(15) . ? C14 C13 1.386(2) . ? C14 H14 0.980(15) . ? C22 C21 1.3923(19) . ? C22 C17 1.4059(19) . ? C22 H22 0.963(15) . ? C12 C13 1.3969(19) . ? C12 H12 0.955(16) . ? C13 H13 0.990(16) . ? C3 H3A 0.984(14) . ? C3 H3B 1.018(15) . ? C19 C20 1.395(2) . ? C19 H19 0.979(17) . ? C23 H23B 1.003(17) . ? C23 H23A 0.975(17) . ? C23 H23C 0.997(17) . ? C21 C20 1.389(2) . ? C21 H21 1.005(17) . ? C20 H20 1.007(17) . ? 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 C6 O1 C23 116.57(10) . . ? C10 C5 C6 120.87(12) . . ? C10 C5 H5 119.5(9) . . ? C6 C5 H5 119.6(9) . . ? C17 N2 C3 115.27(10) . . ? C17 N2 C1 113.43(10) . . ? C3 N2 C1 112.43(10) . . ? C5 C10 C9 119.17(12) . . ? C5 C10 C4 119.64(11) . . ? C9 C10 C4 121.10(11) . . ? C8 C9 C10 119.41(12) . . ? C8 C9 C1 119.50(11) . . ? C10 C9 C1 121.09(11) . . ? O1 C6 C7 123.80(12) . . ? O1 C6 C5 116.00(11) . . ? C7 C6 C5 120.20(12) . . ? C12 C11 C16 118.55(11) . . ? C12 C11 C1 119.15(11) . . ? C16 C11 C1 122.30(11) . . ? C7 C8 C9 121.56(12) . . ? C7 C8 H8 119.0(9) . . ? C9 C8 H8 119.4(9) . . ? F1 C18 C19 118.29(12) . . ? F1 C18 C17 118.33(11) . . ? C19 C18 C17 123.38(13) . . ? C15 C16 C11 120.36(12) . . ? C15 C16 H16 118.6(8) . . ? C11 C16 H16 120.9(8) . . ? C8 C7 C6 118.79(12) . . ? C8 C7 H7 120.0(8) . . ? C6 C7 H7 121.3(8) . . ? C10 C4 C3 114.24(10) . . ? C10 C4 H4A 109.6(9) . . ? C3 C4 H4A 109.1(9) . . ? C10 C4 H4B 107.4(9) . . ? C3 C4 H4B 108.5(9) . . ? H4A C4 H4B 107.7(12) . . ? N2 C1 C9 109.79(10) . . ? N2 C1 C11 112.74(10) . . ? C9 C1 C11 112.04(10) . . ? N2 C1 H1 106.4(8) . . ? C9 C1 H1 108.0(8) . . ? C11 C1 H1 107.5(8) . . ? C16 C15 C14 120.42(12) . . ? C16 C15 H15 119.3(8) . . ? C14 C15 H15 120.2(8) . . ? C13 C14 C15 119.81(12) . . ? C13 C14 H14 121.1(8) . . ? C15 C14 H14 119.1(8) . . ? C21 C22 C17 121.18(13) . . ? C21 C22 H22 120.2(9) . . ? C17 C22 H22 118.6(9) . . ? C11 C12 C13 121.06(12) . . ? C11 C12 H12 119.2(9) . . ? C13 C12 H12 119.8(9) . . ? C18 C17 C22 116.26(12) . . ? C18 C17 N2 119.41(11) . . ? C22 C17 N2 124.31(12) . . ? C14 C13 C12 119.76(12) . . ? C14 C13 H13 121.2(9) . . ? C12 C13 H13 119.0(9) . . ? N2 C3 C4 109.69(10) . . ? N2 C3 H3A 112.1(8) . . ? C4 C3 H3A 110.1(8) . . ? N2 C3 H3B 107.8(8) . . ? C4 C3 H3B 110.0(8) . . ? H3A C3 H3B 107.0(11) . . ? C18 C19 C20 119.13(14) . . ? C18 C19 H19 118.0(10) . . ? C20 C19 H19 122.8(10) . . ? O1 C23 H23B 110.1(9) . . ? O1 C23 H23A 110.0(10) . . ? H23B C23 H23A 110.3(13) . . ? O1 C23 H23C 104.5(10) . . ? H23B C23 H23C 111.1(13) . . ? H23A C23 H23C 110.7(13) . . ? C20 C21 C22 120.74(14) . . ? C20 C21 H21 120.8(9) . . ? C22 C21 H21 118.4(9) . . ? C21 C20 C19 119.27(13) . . ? C21 C20 H20 122.0(10) . . ? C19 C20 H20 118.7(10) . . ? 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 C6 C5 C10 C9 -0.35(18) . . . . ? C6 C5 C10 C4 176.20(11) . . . . ? C5 C10 C9 C8 0.53(17) . . . . ? C4 C10 C9 C8 -175.97(11) . . . . ? C5 C10 C9 C1 -179.03(11) . . . . ? C4 C10 C9 C1 4.47(17) . . . . ? C23 O1 C6 C7 -5.39(18) . . . . ? C23 O1 C6 C5 174.43(12) . . . . ? C10 C5 C6 O1 179.74(11) . . . . ? C10 C5 C6 C7 -0.43(19) . . . . ? C10 C9 C8 C7 0.06(18) . . . . ? C1 C9 C8 C7 179.63(11) . . . . ? C12 C11 C16 C15 1.88(18) . . . . ? C1 C11 C16 C15 -177.49(11) . . . . ? C9 C8 C7 C6 -0.83(18) . . . . ? O1 C6 C7 C8 -179.18(11) . . . . ? C5 C6 C7 C8 1.01(18) . . . . ? C5 C10 C4 C3 171.75(11) . . . . ? C9 C10 C4 C3 -11.77(17) . . . . ? C17 N2 C1 C9 -171.11(10) . . . . ? C3 N2 C1 C9 55.88(13) . . . . ? C17 N2 C1 C11 63.21(13) . . . . ? C3 N2 C1 C11 -69.80(13) . . . . ? C8 C9 C1 N2 155.26(11) . . . . ? C10 C9 C1 N2 -25.18(15) . . . . ? C8 C9 C1 C11 -78.66(14) . . . . ? C10 C9 C1 C11 100.90(13) . . . . ? C12 C11 C1 N2 -95.40(13) . . . . ? C16 C11 C1 N2 83.97(14) . . . . ? C12 C11 C1 C9 140.15(12) . . . . ? C16 C11 C1 C9 -40.48(16) . . . . ? C11 C16 C15 C14 -1.57(19) . . . . ? C16 C15 C14 C13 -0.03(19) . . . . ? C16 C11 C12 C13 -0.65(19) . . . . ? C1 C11 C12 C13 178.75(12) . . . . ? F1 C18 C17 C22 -177.37(11) . . . . ? C19 C18 C17 C22 2.21(19) . . . . ? F1 C18 C17 N2 1.19(17) . . . . ? C19 C18 C17 N2 -179.23(12) . . . . ? C21 C22 C17 C18 -0.72(18) . . . . ? C21 C22 C17 N2 -179.20(12) . . . . ? C3 N2 C17 C18 -161.36(11) . . . . ? C1 N2 C17 C18 67.00(15) . . . . ? C3 N2 C17 C22 17.07(17) . . . . ? C1 N2 C17 C22 -114.56(13) . . . . ? C15 C14 C13 C12 1.3(2) . . . . ? C11 C12 C13 C14 -0.9(2) . . . . ? C17 N2 C3 C4 163.44(10) . . . . ? C1 N2 C3 C4 -64.46(13) . . . . ? C10 C4 C3 N2 40.22(14) . . . . ? F1 C18 C19 C20 177.52(12) . . . . ? C17 C18 C19 C20 -2.1(2) . . . . ? C17 C22 C21 C20 -0.9(2) . . . . ? C22 C21 C20 C19 1.1(2) . . . . ? C18 C19 C20 C21 0.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.343 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.041