# 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_email ymwu@sioc.ac.cn _publ_contact_author_name 'Yong-Ming Wu' loop_ _publ_author_name 'Yong-Ming Wu' 'Yajun Li' 'Jiangtao Zhu' 'Haibo Xie' 'Shan Li' 'Yuefa Gong' data_cd211312 _database_code_depnum_ccdc_archive 'CCDC 842396' #TrackingRef 'web_deposit_cif_file_0_Yong-MingWu_1314780518.cd211312.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H16 F2 N2 O' _chemical_formula_weight 374.38 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.1029(11) _cell_length_b 12.9419(13) _cell_length_c 12.5303(12) _cell_angle_alpha 90.00 _cell_angle_beta 94.973(2) _cell_angle_gamma 90.00 _cell_volume 1793.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4038 _cell_measurement_theta_min 4.534 _cell_measurement_theta_max 54.523 _exptl_crystal_description prismatic _exptl_crystal_colour green _exptl_crystal_size_max 0.318 _exptl_crystal_size_mid 0.167 _exptl_crystal_size_min 0.151 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.77178 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 9435 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0258 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3509 _reflns_number_gt 2890 _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^)+(0.0995P)^2^+0.2931P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3509 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0730 _refine_ls_R_factor_gt 0.0636 _refine_ls_wR_factor_ref 0.1625 _refine_ls_wR_factor_gt 0.1545 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 0.52940(10) 0.06355(11) 0.23634(10) 0.0665(4) Uani 1 1 d . . . F2 F 0.64585(12) 0.00798(9) 0.11842(10) 0.0663(4) Uani 1 1 d . . . N1 N 0.74679(13) 0.20298(11) 0.30482(11) 0.0360(3) Uani 1 1 d . . . N2 N 0.80538(14) 0.03301(12) 0.30223(12) 0.0457(4) Uani 1 1 d . . . O1 O 0.78784(14) -0.38828(11) 0.21420(14) 0.0654(5) Uani 1 1 d . . . C1 C 0.73403(15) 0.10236(13) 0.26531(13) 0.0367(4) Uani 1 1 d . . . C2 C 0.62669(16) 0.09014(14) 0.18088(15) 0.0434(4) Uani 1 1 d . . . C3 C 0.59474(16) 0.18252(15) 0.11283(14) 0.0426(4) Uani 1 1 d . . . C4 C 0.52858(19) 0.17038(19) 0.01383(16) 0.0569(5) Uani 1 1 d . . . H4 H 0.5069 0.1047 -0.0111 0.068 Uiso 1 1 calc R . . C5 C 0.4955(2) 0.2562(2) -0.04692(17) 0.0656(7) Uani 1 1 d . . . H5 H 0.4515 0.2486 -0.1130 0.079 Uiso 1 1 calc R . . C6 C 0.5278(2) 0.35345(19) -0.00949(17) 0.0615(6) Uani 1 1 d . . . H6 H 0.5051 0.4111 -0.0507 0.074 Uiso 1 1 calc R . . C7 C 0.59318(19) 0.36617(17) 0.08768(16) 0.0523(5) Uani 1 1 d . . . H7 H 0.6149 0.4321 0.1118 0.063 Uiso 1 1 calc R . . C8 C 0.62691(16) 0.28022(14) 0.15015(14) 0.0405(4) Uani 1 1 d . . . C9 C 0.69887(16) 0.29093(13) 0.25269(13) 0.0378(4) Uani 1 1 d . . . C10 C 0.73480(17) 0.37563(14) 0.30984(15) 0.0449(4) Uani 1 1 d . . . H10 H 0.7147 0.4436 0.2921 0.054 Uiso 1 1 calc R . . C11 C 0.80906(16) 0.34257(14) 0.40239(14) 0.0410(4) Uani 1 1 d . . . C12 C 0.81586(15) 0.23409(13) 0.39851(13) 0.0359(4) Uani 1 1 d . . . C13 C 0.87932(16) 0.17806(15) 0.47899(14) 0.0430(4) Uani 1 1 d . . . H13 H 0.8818 0.1063 0.4770 0.052 Uiso 1 1 calc R . . C14 C 0.93872(18) 0.23265(17) 0.56233(15) 0.0520(5) Uani 1 1 d . . . H14 H 0.9825 0.1968 0.6171 0.062 Uiso 1 1 calc R . . C15 C 0.93470(19) 0.33925(18) 0.56648(16) 0.0570(5) Uani 1 1 d . . . H15 H 0.9762 0.3737 0.6235 0.068 Uiso 1 1 calc R . . C16 C 0.87038(18) 0.39519(16) 0.48778(16) 0.0526(5) Uani 1 1 d . . . H16 H 0.8677 0.4669 0.4913 0.063 Uiso 1 1 calc R . . C17 C 0.79740(16) -0.07275(14) 0.27414(14) 0.0420(4) Uani 1 1 d . . . C18 C 0.87053(18) -0.11388(14) 0.20158(16) 0.0474(5) Uani 1 1 d . . . H18 H 0.9220 -0.0705 0.1676 0.057 Uiso 1 1 calc R . . C19 C 0.86912(18) -0.21797(14) 0.17821(15) 0.0461(5) Uani 1 1 d . . . H19 H 0.9175 -0.2439 0.1274 0.055 Uiso 1 1 calc R . . C20 C 0.79552(17) -0.28380(14) 0.23052(16) 0.0438(4) Uani 1 1 d . . . C21 C 0.72402(19) -0.24398(16) 0.30516(18) 0.0543(5) Uani 1 1 d . . . H21 H 0.6749 -0.2878 0.3411 0.065 Uiso 1 1 calc R . . C22 C 0.72495(18) -0.13981(16) 0.32672(18) 0.0537(5) Uani 1 1 d . . . H22 H 0.6763 -0.1139 0.3773 0.064 Uiso 1 1 calc R . . C23 C 0.8638(2) -0.43229(17) 0.1414(2) 0.0711(7) Uani 1 1 d . . . H23A H 0.8436 -0.4042 0.0712 0.107 Uiso 1 1 calc R . . H23B H 0.8528 -0.5059 0.1395 0.107 Uiso 1 1 calc R . . H23C H 0.9466 -0.4166 0.1640 0.107 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 0.0477(7) 0.0799(9) 0.0705(8) 0.0153(7) -0.0028(6) -0.0165(6) F2 0.0876(9) 0.0487(7) 0.0571(7) -0.0182(5) -0.0257(6) 0.0109(6) N1 0.0408(8) 0.0354(7) 0.0310(7) -0.0012(5) -0.0013(6) 0.0000(6) N2 0.0499(9) 0.0376(8) 0.0480(9) -0.0038(6) -0.0056(7) 0.0035(6) O1 0.0741(10) 0.0355(8) 0.0905(12) -0.0088(7) 0.0289(9) -0.0065(7) C1 0.0409(9) 0.0352(9) 0.0340(9) -0.0011(7) 0.0034(7) -0.0014(7) C2 0.0450(10) 0.0422(10) 0.0419(10) -0.0068(8) -0.0023(7) -0.0029(7) C3 0.0379(9) 0.0528(11) 0.0367(9) -0.0036(8) 0.0008(7) 0.0073(8) C4 0.0512(11) 0.0719(14) 0.0455(11) -0.0096(10) -0.0078(9) 0.0085(10) C5 0.0589(13) 0.0993(19) 0.0361(11) 0.0024(11) -0.0092(9) 0.0246(12) C6 0.0640(13) 0.0715(15) 0.0487(12) 0.0138(11) 0.0025(10) 0.0277(11) C7 0.0545(11) 0.0542(11) 0.0481(11) 0.0087(9) 0.0034(9) 0.0158(9) C8 0.0401(9) 0.0479(10) 0.0339(9) 0.0019(7) 0.0057(7) 0.0087(7) C9 0.0437(9) 0.0363(9) 0.0336(9) 0.0024(7) 0.0047(7) 0.0043(7) C10 0.0552(11) 0.0344(9) 0.0453(10) 0.0021(7) 0.0052(8) 0.0030(7) C11 0.0458(10) 0.0384(9) 0.0393(9) -0.0037(7) 0.0064(7) -0.0033(7) C12 0.0361(9) 0.0396(9) 0.0321(9) -0.0037(7) 0.0034(7) -0.0034(7) C13 0.0474(10) 0.0439(10) 0.0368(10) 0.0010(7) -0.0013(7) -0.0026(7) C14 0.0521(12) 0.0654(13) 0.0366(10) -0.0029(9) -0.0065(8) -0.0001(9) C15 0.0590(13) 0.0651(14) 0.0452(11) -0.0173(9) -0.0051(9) -0.0087(10) C16 0.0601(12) 0.0452(11) 0.0520(12) -0.0127(8) 0.0022(9) -0.0070(9) C17 0.0438(9) 0.0371(9) 0.0435(10) -0.0012(7) -0.0059(7) 0.0050(7) C18 0.0581(11) 0.0375(10) 0.0473(11) 0.0067(8) 0.0089(9) -0.0006(8) C19 0.0542(11) 0.0411(10) 0.0441(10) 0.0001(8) 0.0109(8) 0.0049(8) C20 0.0458(10) 0.0344(9) 0.0507(11) -0.0005(7) 0.0022(8) -0.0004(7) C21 0.0512(11) 0.0481(11) 0.0664(13) -0.0022(9) 0.0202(10) -0.0077(9) C22 0.0511(11) 0.0486(11) 0.0635(13) -0.0080(9) 0.0180(9) 0.0004(9) C23 0.0914(17) 0.0423(12) 0.0825(17) -0.0140(11) 0.0248(14) -0.0007(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 1.378(2) . ? F2 C2 1.348(2) . ? N1 C9 1.395(2) . ? N1 C1 1.396(2) . ? N1 C12 1.404(2) . ? N2 C1 1.258(2) . ? N2 C17 1.414(2) . ? O1 C20 1.369(2) . ? O1 C23 1.415(3) . ? C1 C2 1.532(2) . ? C2 C3 1.493(3) . ? C3 C8 1.384(3) . ? C3 C4 1.395(3) . ? C4 C5 1.378(3) . ? C4 H4 0.9300 . ? C5 C6 1.380(4) . ? C5 H5 0.9300 . ? C6 C7 1.372(3) . ? C6 H6 0.9300 . ? C7 C8 1.393(3) . ? C7 H7 0.9300 . ? C8 C9 1.460(2) . ? C9 C10 1.351(3) . ? C10 C11 1.429(3) . ? C10 H10 0.9300 . ? C11 C16 1.395(3) . ? C11 C12 1.407(2) . ? C12 C13 1.384(2) . ? C13 C14 1.380(3) . ? C13 H13 0.9300 . ? C14 C15 1.382(3) . ? C14 H14 0.9300 . ? C15 C16 1.373(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.377(3) . ? C17 C22 1.388(3) . ? C18 C19 1.379(3) . ? C18 H18 0.9300 . ? C19 C20 1.384(3) . ? C19 H19 0.9300 . ? C20 C21 1.378(3) . ? C21 C22 1.375(3) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? 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 C9 N1 C1 124.92(14) . . ? C9 N1 C12 108.42(14) . . ? C1 N1 C12 126.52(14) . . ? C1 N2 C17 125.09(15) . . ? C20 O1 C23 117.45(16) . . ? N2 C1 N1 119.58(15) . . ? N2 C1 C2 127.42(16) . . ? N1 C1 C2 112.96(14) . . ? F2 C2 F1 105.42(15) . . ? F2 C2 C3 109.98(15) . . ? F1 C2 C3 109.28(15) . . ? F2 C2 C1 109.26(14) . . ? F1 C2 C1 105.93(14) . . ? C3 C2 C1 116.35(15) . . ? C8 C3 C4 120.27(18) . . ? C8 C3 C2 119.79(16) . . ? C4 C3 C2 119.90(18) . . ? C5 C4 C3 119.7(2) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 119.9(2) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C7 C6 C5 120.9(2) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C8 119.9(2) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C3 C8 C7 119.39(18) . . ? C3 C8 C9 119.32(16) . . ? C7 C8 C9 121.26(17) . . ? C10 C9 N1 109.33(15) . . ? C10 C9 C8 131.13(16) . . ? N1 C9 C8 119.48(15) . . ? C9 C10 C11 108.08(16) . . ? C9 C10 H10 126.0 . . ? C11 C10 H10 126.0 . . ? C16 C11 C12 119.32(17) . . ? C16 C11 C10 133.25(18) . . ? C12 C11 C10 107.44(15) . . ? C13 C12 N1 131.71(16) . . ? C13 C12 C11 121.53(16) . . ? N1 C12 C11 106.73(14) . . ? C14 C13 C12 117.56(18) . . ? C14 C13 H13 121.2 . . ? C12 C13 H13 121.2 . . ? C13 C14 C15 121.65(19) . . ? C13 C14 H14 119.2 . . ? C15 C14 H14 119.2 . . ? C16 C15 C14 121.07(18) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C11 118.84(19) . . ? C15 C16 H16 120.6 . . ? C11 C16 H16 120.6 . . ? C18 C17 C22 118.09(17) . . ? C18 C17 N2 120.70(17) . . ? C22 C17 N2 120.89(17) . . ? C17 C18 C19 121.43(18) . . ? C17 C18 H18 119.3 . . ? C19 C18 H18 119.3 . . ? C18 C19 C20 119.81(17) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? O1 C20 C21 116.01(17) . . ? O1 C20 C19 124.66(17) . . ? C21 C20 C19 119.32(17) . . ? C22 C21 C20 120.34(18) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C21 C22 C17 120.97(18) . . ? C21 C22 H22 119.5 . . ? C17 C22 H22 119.5 . . ? O1 C23 H23A 109.5 . . ? O1 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O1 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? 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 N1 175.73(16) . . . . ? C17 N2 C1 C2 -2.0(3) . . . . ? C9 N1 C1 N2 160.97(17) . . . . ? C12 N1 C1 N2 -14.2(3) . . . . ? C9 N1 C1 C2 -21.0(2) . . . . ? C12 N1 C1 C2 163.81(15) . . . . ? N2 C1 C2 F2 -25.7(3) . . . . ? N1 C1 C2 F2 156.43(15) . . . . ? N2 C1 C2 F1 87.4(2) . . . . ? N1 C1 C2 F1 -90.45(17) . . . . ? N2 C1 C2 C3 -150.93(18) . . . . ? N1 C1 C2 C3 31.2(2) . . . . ? F2 C2 C3 C8 -148.82(17) . . . . ? F1 C2 C3 C8 95.91(19) . . . . ? C1 C2 C3 C8 -24.0(2) . . . . ? F2 C2 C3 C4 33.7(2) . . . . ? F1 C2 C3 C4 -81.6(2) . . . . ? C1 C2 C3 C4 158.54(17) . . . . ? C8 C3 C4 C5 0.1(3) . . . . ? C2 C3 C4 C5 177.62(19) . . . . ? C3 C4 C5 C6 -0.1(3) . . . . ? C4 C5 C6 C7 0.2(3) . . . . ? C5 C6 C7 C8 -0.5(3) . . . . ? C4 C3 C8 C7 -0.4(3) . . . . ? C2 C3 C8 C7 -177.85(17) . . . . ? C4 C3 C8 C9 -178.40(17) . . . . ? C2 C3 C8 C9 4.1(3) . . . . ? C6 C7 C8 C3 0.5(3) . . . . ? C6 C7 C8 C9 178.52(18) . . . . ? C1 N1 C9 C10 -176.08(16) . . . . ? C12 N1 C9 C10 -0.1(2) . . . . ? C1 N1 C9 C8 1.6(2) . . . . ? C12 N1 C9 C8 177.53(14) . . . . ? C3 C8 C9 C10 -174.92(19) . . . . ? C7 C8 C9 C10 7.1(3) . . . . ? C3 C8 C9 N1 8.0(2) . . . . ? C7 C8 C9 N1 -169.99(16) . . . . ? N1 C9 C10 C11 0.2(2) . . . . ? C8 C9 C10 C11 -177.10(17) . . . . ? C9 C10 C11 C16 179.6(2) . . . . ? C9 C10 C11 C12 -0.2(2) . . . . ? C9 N1 C12 C13 178.24(18) . . . . ? C1 N1 C12 C13 -5.9(3) . . . . ? C9 N1 C12 C11 0.00(18) . . . . ? C1 N1 C12 C11 175.87(15) . . . . ? C16 C11 C12 C13 1.8(3) . . . . ? C10 C11 C12 C13 -178.34(16) . . . . ? C16 C11 C12 N1 -179.75(16) . . . . ? C10 C11 C12 N1 0.11(18) . . . . ? N1 C12 C13 C14 -179.68(17) . . . . ? C11 C12 C13 C14 -1.7(3) . . . . ? C12 C13 C14 C15 0.5(3) . . . . ? C13 C14 C15 C16 0.5(3) . . . . ? C14 C15 C16 C11 -0.4(3) . . . . ? C12 C11 C16 C15 -0.7(3) . . . . ? C10 C11 C16 C15 179.4(2) . . . . ? C1 N2 C17 C18 100.5(2) . . . . ? C1 N2 C17 C22 -86.2(2) . . . . ? C22 C17 C18 C19 2.4(3) . . . . ? N2 C17 C18 C19 176.00(17) . . . . ? C17 C18 C19 C20 -1.9(3) . . . . ? C23 O1 C20 C21 -177.4(2) . . . . ? C23 O1 C20 C19 2.3(3) . . . . ? C18 C19 C20 O1 -179.44(19) . . . . ? C18 C19 C20 C21 0.3(3) . . . . ? O1 C20 C21 C22 -179.6(2) . . . . ? C19 C20 C21 C22 0.6(3) . . . . ? C20 C21 C22 C17 0.0(3) . . . . ? C18 C17 C22 C21 -1.5(3) . . . . ? N2 C17 C22 C21 -175.07(19) . . . . ? 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 C10 H10 O1 0.93 2.55 3.353(2) 145.3 1_565 C4 H4 F2 0.93 2.53 3.357(3) 147.8 3_655 C6 H6 F1 0.93 2.73 3.363(3) 126.5 4_565 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.437 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.091