data_General _audit_creation_date 2014-01-08 _audit_creation_method 'by CrystalStructure 4.0' _audit_update_record ? #============================================================================== # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_coeditor_code ? #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'Noboru Koga' _publ_contact_author_address '3-1-1 Maidashi, Higashi-ku, Fukuoka, Japan' _publ_contact_author_email 'koga@fc.phar.kyushu-u.ac.jp' _publ_contact_author_fax '81-92-642-6545' _publ_contact_author_phone '81-92-642-6590' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_journal 'Chemistry A Europian Journal' _publ_requested_category 'FO' _publ_requested_coeditor_name ? #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; ENTER SECTION TITLE ; _publ_section_title_footnote ; ENTER FOOTNOTE TO TITLE OF PAPER ; loop_ _publ_author_name _publ_author_footnote _publ_author_address ' FIRST AUTHORS NAME ' ; FIRST AUTHORS FOOTNOTES ; ; FIRST AUTHORS ADDRESS ; _publ_section_synopsis ; ENTER SYNOPSIS ; #============================================================================== # TEXT _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Rigaku (2010). CrystalStructure. Version 4.0. Rigaku Corporation, Tokyo, Japan. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M., Polidori, G., and Camalli, M. (1994) J. Appl. Cryst., 27, 435. SIR92 Sheldrick, G.M. (2008), Acta Cryst. A64, 112-122. ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _publ_section_exptl_prep ; ENTER COMPOUND PREPARATION DETAILS ; _publ_section_exptl_refinement ; ENTER SPECIAL DETAILS OF THE REFINEMENT ; #============================================================================== data_PE_anti #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C19 H14 F6 N2' _chemical_formula_moiety 'C19 H14 F6 N2' _chemical_formula_weight 384.32 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 '+X,+Y,+Z' 2 '-X,-Y,-Z' #------------------------------------------------------------------------------ _cell_length_a 8.858(3) _cell_length_b 9.351(3) _cell_length_c 11.404(4) _cell_angle_alpha 81.884(4) _cell_angle_beta 89.636(4) _cell_angle_gamma 65.688(3) _cell_volume 850.7(5) _cell_formula_units_Z 2 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_measurement_temperature 90 #------------------------------------------------------------------------------ _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.500 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392.00 _exptl_absorpt_coefficient_mu 0.135 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 90 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_measurement_device_type 'Unknown CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 4593 _diffrn_reflns_av_R_equivalents 0.0165 _diffrn_reflns_theta_max 26.70 _diffrn_reflns_theta_full 26.70 _diffrn_measured_fraction_theta_max 0.961 _diffrn_measured_fraction_theta_full 0.961 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 14 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3466 _reflns_number_gt 2923 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0914 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment refxyz _refine_ls_number_reflns 3466 _refine_ls_number_parameters 300 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0415P)^2^+0.2994P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.360 _refine_diff_density_min -0.240 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; 'H' 'H' 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; 'N' 'N' 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; 'F' 'F' 0.0171 0.0103 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 C8 C 0.35654(16) 0.29817(16) 0.50096(12) 0.0183(3) Uani 1.0 2 d . . . C2 C 0.48285(16) 0.16297(15) 0.22365(12) 0.0185(3) Uani 1.0 2 d . . . C9 C 0.27087(16) 0.27398(15) 0.59830(12) 0.0180(3) Uani 1.0 2 d . . . C6 C 0.30073(16) 0.10365(15) 0.40352(11) 0.0173(3) Uani 1.0 2 d . . . C4 C 0.31983(16) 0.02837(15) 0.30174(12) 0.0186(3) Uani 1.0 2 d . . . C11 C 0.21429(16) 0.08002(15) 0.50461(12) 0.0191(3) Uani 1.0 2 d . . . C7 C 0.37564(15) 0.21319(15) 0.40492(12) 0.0175(3) Uani 1.0 2 d . . . C3 C 0.23545(18) -0.08044(16) 0.28927(12) 0.0226(3) Uani 1.0 2 d . . . C10 C 0.20131(16) 0.15973(15) 0.59802(12) 0.0191(3) Uani 1.0 2 d . . . C5 C 0.41168(16) 0.05614(16) 0.21131(12) 0.0195(3) Uani 1.0 2 d . . . C12 C 0.13206(16) 0.35266(15) 0.77988(12) 0.0194(3) Uani 1.0 2 d . . . C1 C 0.58834(17) 0.19638(16) 0.12866(12) 0.0213(3) Uani 1.0 2 d . . . C13 C -0.03522(17) 0.41901(16) 0.74232(13) 0.0224(3) Uani 1.0 2 d . . . C14 C -0.15376(18) 0.42238(17) 0.82361(14) 0.0263(4) Uani 1.0 2 d . . . C15 C -0.1061(2) 0.36225(18) 0.94188(15) 0.0302(4) Uani 1.0 2 d . . . C16 C 0.0597(3) 0.2986(2) 0.97935(14) 0.0333(4) Uani 1.0 2 d . . . C17 C 0.31907(18) 0.47149(17) 0.69873(13) 0.0231(3) Uani 1.0 2 d . . . C18 C 0.2012(2) 0.63197(18) 0.63325(15) 0.0288(4) Uani 1.0 2 d . . . F2 F 0.28077(11) -0.20354(9) 0.37743(7) 0.0276(2) Uani 1.0 2 d . . . F4 F 0.74446(10) 0.15199(12) 0.16893(8) 0.0353(3) Uani 1.0 2 d . . . F6 F 0.59556(12) 0.12022(12) 0.03644(8) 0.0354(3) Uani 1.0 2 d . . . F1 F 0.06952(10) -0.00339(11) 0.29026(8) 0.0327(3) Uani 1.0 2 d . . . F5 F 0.53112(12) 0.35060(10) 0.08532(9) 0.0379(3) Uani 1.0 2 d . . . F3 F 0.26826(13) -0.14117(12) 0.18829(8) 0.0385(3) Uani 1.0 2 d . . . C19 C 0.17931(19) 0.29272(18) 0.89855(13) 0.0266(4) Uani 1.0 2 d . . . N2 N 0.46673(13) 0.24031(13) 0.31420(10) 0.0182(3) Uani 1.0 2 d . . . N1 N 0.25676(14) 0.34793(13) 0.69717(10) 0.0196(3) Uani 1.0 2 d . . . H1 H 0.4051(19) 0.3723(18) 0.4950(14) 0.019(4) Uiso 1.0 2 d . . . H3 H 0.1661(19) 0.0006(18) 0.5088(13) 0.019(4) Uiso 1.0 2 d . . . H2 H 0.1464(19) 0.1401(18) 0.6663(14) 0.017(4) Uiso 1.0 2 d . . . H4 H 0.429(2) 0.005(2) 0.1439(16) 0.029(5) Uiso 1.0 2 d . . . H9 H -0.069(2) 0.464(2) 0.6611(16) 0.028(5) Uiso 1.0 2 d . . . H5 H 0.294(3) 0.249(2) 0.9217(16) 0.032(5) Uiso 1.0 2 d . . . H8 H -0.267(3) 0.466(2) 0.7985(15) 0.031(5) Uiso 1.0 2 d . . . H7 H -0.187(3) 0.369(3) 0.9963(17) 0.036(5) Uiso 1.0 2 d . . . H6 H 0.091(3) 0.257(3) 1.0619(18) 0.044(6) Uiso 1.0 2 d . . . H10 H 0.428(2) 0.4361(19) 0.6668(15) 0.025(4) Uiso 1.0 2 d . . . H11 H 0.337(2) 0.478(2) 0.7808(16) 0.030(5) Uiso 1.0 2 d . . . H13 H 0.180(3) 0.624(3) 0.5509(17) 0.034(5) Uiso 1.0 2 d . . . H12 H 0.095(3) 0.670(3) 0.6725(16) 0.038(5) Uiso 1.0 2 d . . . H14 H 0.247(2) 0.708(2) 0.6346(15) 0.031(5) Uiso 1.0 2 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C8 0.0176(7) 0.0208(6) 0.0197(7) -0.0102(5) 0.0016(6) -0.0058(6) C2 0.0162(6) 0.0204(7) 0.0173(7) -0.0059(5) 0.0005(5) -0.0031(6) C9 0.0159(6) 0.0185(6) 0.0173(7) -0.0044(5) -0.0008(5) -0.0044(5) C6 0.0165(6) 0.0179(6) 0.0170(7) -0.0065(5) 0.0000(5) -0.0033(5) C4 0.0176(6) 0.0186(6) 0.0205(7) -0.0081(5) 0.0002(6) -0.0042(6) C11 0.0191(7) 0.0188(6) 0.0209(7) -0.0090(5) 0.0017(6) -0.0040(6) C7 0.0149(6) 0.0182(6) 0.0175(7) -0.0050(5) -0.0005(5) -0.0025(5) C3 0.0269(8) 0.0257(7) 0.0201(7) -0.0144(6) 0.0034(6) -0.0084(6) C10 0.0188(7) 0.0199(6) 0.0180(7) -0.0074(5) 0.0034(6) -0.0031(6) C5 0.0208(7) 0.0211(7) 0.0172(7) -0.0081(6) 0.0008(6) -0.0068(6) C12 0.0208(7) 0.0189(6) 0.0202(7) -0.0084(5) 0.0047(6) -0.0081(6) C1 0.0223(7) 0.0239(7) 0.0196(7) -0.0105(6) 0.0018(6) -0.0064(6) C13 0.0233(7) 0.0215(7) 0.0223(8) -0.0086(6) 0.0022(6) -0.0050(6) C14 0.0214(7) 0.0228(7) 0.0371(9) -0.0093(6) 0.0069(7) -0.0115(7) C15 0.0348(9) 0.0293(8) 0.0318(9) -0.0167(7) 0.0171(7) -0.0113(7) C16 0.0411(10) 0.0365(9) 0.0205(8) -0.0152(7) 0.0058(7) -0.0022(7) C17 0.0235(8) 0.0304(8) 0.0222(8) -0.0154(6) 0.0043(6) -0.0121(6) C18 0.0326(9) 0.0277(8) 0.0325(9) -0.0174(7) 0.0052(7) -0.0089(7) F2 0.0334(5) 0.0239(4) 0.0300(5) -0.0166(4) 0.0025(4) -0.0036(4) F4 0.0210(5) 0.0606(7) 0.0261(5) -0.0198(5) 0.0039(4) -0.0032(5) F6 0.0475(6) 0.0529(6) 0.0235(5) -0.0341(5) 0.0169(4) -0.0207(5) F1 0.0236(5) 0.0346(5) 0.0449(6) -0.0166(4) -0.0037(4) -0.0075(4) F5 0.0408(6) 0.0270(5) 0.0403(6) -0.0108(4) 0.0201(5) 0.0013(4) F3 0.0629(7) 0.0507(6) 0.0271(5) -0.0438(6) 0.0164(5) -0.0221(5) C19 0.0259(8) 0.0286(8) 0.0220(8) -0.0077(6) 0.0007(6) -0.0047(6) N2 0.0178(6) 0.0202(6) 0.0173(6) -0.0081(5) 0.0009(5) -0.0044(5) N1 0.0204(6) 0.0237(6) 0.0175(6) -0.0104(5) 0.0033(5) -0.0075(5) #============================================================================== _computing_data_collection Unknown _computing_cell_refinement Unknown _computing_data_reduction Unknown _computing_structure_solution 'SIR92 (Altomare, et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 C8 C9 1.385(2) yes . . C8 C7 1.411(3) yes . . C2 C5 1.405(3) yes . . C2 C1 1.509(3) yes . . C2 N2 1.317(2) yes . . C9 C10 1.437(3) yes . . C9 N1 1.383(2) yes . . C6 C4 1.415(2) yes . . C6 C11 1.421(2) yes . . C6 C7 1.433(3) yes . . C4 C3 1.511(3) yes . . C4 C5 1.371(2) yes . . C11 C10 1.362(3) yes . . C7 N2 1.3673(19) yes . . C3 F2 1.3397(15) yes . . C3 F1 1.3452(17) yes . . C3 F3 1.3332(18) yes . . C12 C13 1.393(2) yes . . C12 C19 1.386(2) yes . . C12 N1 1.4387(19) yes . . C1 F4 1.3331(18) yes . . C1 F6 1.3380(19) yes . . C1 F5 1.3345(17) yes . . C13 C14 1.390(3) yes . . C14 C15 1.382(3) yes . . C15 C16 1.382(3) yes . . C16 C19 1.388(3) yes . . C17 C18 1.5176(19) yes . . C17 N1 1.473(3) yes . . C8 H1 0.95(2) no . . C11 H3 0.99(2) no . . C10 H2 0.951(17) no . . C5 H4 0.940(19) no . . C13 H9 0.956(17) no . . C14 H8 0.941(18) no . . C15 H7 0.93(2) no . . C16 H6 0.96(2) no . . C17 H10 0.971(18) no . . C17 H11 0.964(19) no . . C18 H13 0.98(2) no . . C18 H12 0.99(2) no . . C18 H14 0.96(3) no . . C19 H5 0.946(19) no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C9 C8 C7 121.27(16) yes . . . C5 C2 C1 120.13(13) yes . . . C5 C2 N2 125.36(14) yes . . . C1 C2 N2 114.51(15) yes . . . C8 C9 C10 117.70(14) yes . . . C8 C9 N1 123.30(16) yes . . . C10 C9 N1 118.91(13) yes . . . C4 C6 C11 125.83(16) yes . . . C4 C6 C7 117.07(13) yes . . . C11 C6 C7 117.11(13) yes . . . C6 C4 C3 120.56(13) yes . . . C6 C4 C5 120.58(16) yes . . . C3 C4 C5 118.84(14) yes . . . C6 C11 C10 121.41(16) yes . . . C8 C7 C6 120.60(13) yes . . . C8 C7 N2 117.53(15) yes . . . C6 C7 N2 121.88(13) yes . . . C4 C3 F2 112.91(13) yes . . . C4 C3 F1 111.44(12) yes . . . C4 C3 F3 112.15(14) yes . . . F2 C3 F1 106.15(13) yes . . . F2 C3 F3 106.71(12) yes . . . F1 C3 F3 107.08(13) yes . . . C9 C10 C11 121.84(14) yes . . . C2 C5 C4 117.36(14) yes . . . C13 C12 C19 119.83(14) yes . . . C13 C12 N1 120.77(12) yes . . . C19 C12 N1 119.40(13) yes . . . C2 C1 F4 112.21(11) yes . . . C2 C1 F6 112.32(15) yes . . . C2 C1 F5 112.18(11) yes . . . F4 C1 F6 106.58(11) yes . . . F4 C1 F5 106.40(14) yes . . . F6 C1 F5 106.74(11) yes . . . C12 C13 C14 119.88(13) yes . . . C13 C14 C15 120.11(15) yes . . . C14 C15 C16 119.94(16) yes . . . C15 C16 C19 120.38(15) yes . . . C18 C17 N1 112.83(14) yes . . . C12 C19 C16 119.85(14) yes . . . C2 N2 C7 117.71(15) yes . . . C9 N1 C12 120.37(14) yes . . . C9 N1 C17 120.61(13) yes . . . C12 N1 C17 115.12(12) yes . . . C9 C8 H1 122.2(10) no . . . C7 C8 H1 116.5(10) no . . . C6 C11 H3 119.4(9) no . . . C10 C11 H3 119.1(9) no . . . C9 C10 H2 117.6(12) no . . . C11 C10 H2 120.5(12) no . . . C2 C5 H4 120.5(13) no . . . C4 C5 H4 122.1(13) no . . . C12 C13 H9 120.1(11) no . . . C14 C13 H9 120.0(11) no . . . C13 C14 H8 120.2(11) no . . . C15 C14 H8 119.7(11) no . . . C14 C15 H7 119.4(11) no . . . C16 C15 H7 120.6(11) no . . . C15 C16 H6 119.0(13) no . . . C19 C16 H6 120.6(13) no . . . C18 C17 H10 111.4(9) no . . . C18 C17 H11 110.8(10) no . . . N1 C17 H10 109.1(12) no . . . N1 C17 H11 107.1(13) no . . . H10 C17 H11 105.2(15) no . . . C17 C18 H13 110.3(10) no . . . C17 C18 H12 109.7(10) no . . . C17 C18 H14 110.3(9) no . . . H13 C18 H12 109.0(16) no . . . H13 C18 H14 109.4(17) no . . . H12 C18 H14 108.2(17) no . . . C12 C19 H5 118.0(11) no . . . C16 C19 H5 122.1(11) no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C9 C8 C7 C6 2.53(16) no . . . . C9 C8 C7 N2 -177.83(9) no . . . . C7 C8 C9 C10 -0.27(16) no . . . . C7 C8 C9 N1 176.34(9) no . . . . C5 C2 C1 F4 -117.26(13) no . . . . C5 C2 C1 F6 2.79(15) no . . . . C5 C2 C1 F5 123.03(13) no . . . . C1 C2 C5 C4 178.73(9) no . . . . C5 C2 N2 C7 1.11(16) no . . . . N2 C2 C5 C4 -0.98(17) no . . . . C1 C2 N2 C7 -178.62(8) no . . . . N2 C2 C1 F4 62.49(14) no . . . . N2 C2 C1 F6 -177.47(9) no . . . . N2 C2 C1 F5 -57.23(15) no . . . . C8 C9 C10 C11 -1.70(16) no . . . . C8 C9 N1 C12 163.15(10) no . . . . C8 C9 N1 C17 6.47(16) no . . . . C10 C9 N1 C12 -20.29(14) no . . . . C10 C9 N1 C17 -176.97(9) no . . . . N1 C9 C10 C11 -178.45(9) no . . . . C4 C6 C11 C10 -179.30(10) no . . . . C11 C6 C4 C3 4.25(16) no . . . . C11 C6 C4 C5 -177.47(10) no . . . . C4 C6 C7 C8 177.36(9) no . . . . C4 C6 C7 N2 -2.26(15) no . . . . C7 C6 C4 C3 -175.93(9) no . . . . C7 C6 C4 C5 2.35(15) no . . . . C11 C6 C7 C8 -2.80(15) no . . . . C11 C6 C7 N2 177.58(9) no . . . . C7 C6 C11 C10 0.89(15) no . . . . C6 C4 C3 F2 -59.03(14) no . . . . C6 C4 C3 F1 60.33(14) no . . . . C6 C4 C3 F3 -179.63(9) no . . . . C6 C4 C5 C2 -0.86(16) no . . . . C3 C4 C5 C2 177.46(9) no . . . . C5 C4 C3 F2 122.65(12) no . . . . C5 C4 C3 F1 -117.98(12) no . . . . C5 C4 C3 F3 2.06(15) no . . . . C6 C11 C10 C9 1.37(16) no . . . . C8 C7 N2 C2 -179.05(9) no . . . . C6 C7 N2 C2 0.59(15) no . . . . C13 C12 C19 C16 0.2(3) no . . . . C19 C12 C13 C14 -1.1(3) no . . . . C13 C12 N1 C9 -57.18(17) no . . . . C13 C12 N1 C17 100.71(16) no . . . . N1 C12 C13 C14 179.98(12) no . . . . C19 C12 N1 C9 123.89(15) no . . . . C19 C12 N1 C17 -78.22(15) no . . . . N1 C12 C19 C16 179.15(13) no . . . . C12 C13 C14 C15 1.0(3) no . . . . C13 C14 C15 C16 -0.0(3) no . . . . C14 C15 C16 C19 -0.9(3) no . . . . C15 C16 C19 C12 0.8(3) no . . . . C18 C17 N1 C9 79.49(14) no . . . . C18 C17 N1 C12 -78.35(14) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 C8 C2 3.573(3) no . . C8 C11 2.800(3) no . . C8 C17 2.899(3) no . . C8 C18 3.417(3) no . . C2 C6 2.737(2) no . . C9 C6 2.861(3) no . . C9 C13 3.071(2) no . . C9 C18 3.228(3) no . . C9 C19 3.525(3) no . . C6 F2 3.005(2) no . . C6 F1 2.992(2) no . . C4 N2 2.801(3) no . . C11 C3 3.020(3) no . . C11 F2 3.0447(19) no . . C11 F1 3.103(2) no . . C7 C10 2.787(2) no . . C7 C5 2.767(3) no . . C10 C12 2.839(3) no . . C10 C13 3.143(2) no . . C5 F2 3.438(2) no . . C5 F4 3.429(3) no . . C5 F6 2.7228(19) no . . C5 F1 3.394(2) no . . C5 F5 3.468(2) no . . C5 F3 2.675(3) no . . C12 C15 2.777(3) no . . C12 C18 3.172(3) no . . C13 C16 2.770(3) no . . C13 C17 3.393(3) no . . C13 C18 3.549(3) no . . C14 C19 2.775(3) no . . C17 C19 3.180(3) no . . F4 N2 2.8531(16) no . . F6 N2 3.5355(18) no . . F5 N2 2.8119(17) no . . C8 F2 3.2243(19) no . 2_656 C2 C10 3.5293(17) no . 2_656 C11 C7 3.5810(18) no . 2_656 C11 N2 3.5472(16) no . 2_656 C7 C11 3.5810(18) no . 2_656 C10 C2 3.5293(17) no . 2_656 C10 F4 3.5307(18) no . 2_656 C10 F1 3.441(2) no . 2_556 C5 F6 3.480(2) no . 2_655 C14 F5 3.3902(18) no . 2_566 C14 F3 3.203(3) no . 2_556 C14 N2 3.3999(17) no . 2_566 C15 C16 3.593(3) no . 2_567 C15 F5 3.5965(19) no . 2_566 C15 F3 3.447(3) no . 2_556 C16 C15 3.593(3) no . 2_567 C16 C16 3.569(3) no . 2_567 C17 F2 3.5858(18) no . 2_656 C18 F2 3.313(2) no . 1_565 C18 F4 3.392(3) no . 2_666 C18 F1 3.5418(19) no . 2_566 F2 C8 3.2243(19) no . 2_656 F2 C17 3.5858(18) no . 2_656 F2 C18 3.313(2) no . 1_545 F4 C10 3.5307(18) no . 2_656 F4 C18 3.392(3) no . 2_666 F4 F1 2.8903(14) no . 1_655 F6 C5 3.480(2) no . 2_655 F6 F6 3.506(2) no . 2_655 F6 F3 2.8416(15) no . 2_655 F6 C19 3.508(2) no . 2_656 F1 C10 3.441(2) no . 2_556 F1 C18 3.5418(19) no . 2_566 F1 F4 2.8903(14) no . 1_455 F5 C14 3.3902(18) no . 2_566 F5 C15 3.5965(19) no . 2_566 F5 F5 3.0178(15) no . 2_665 F3 C14 3.203(3) no . 2_556 F3 C15 3.447(3) no . 2_556 F3 F6 2.8416(15) no . 2_655 C19 F6 3.508(2) no . 2_656 N2 C11 3.5472(16) no . 2_656 N2 C14 3.3999(17) no . 2_566 C8 H2 3.262(18) no . . C8 H10 2.65(2) no . . C8 H13 2.931(18) no . . C9 H3 3.34(2) no . . C9 H9 2.942(16) no . . C9 H10 2.63(3) no . . C9 H11 3.22(2) no . . C9 H13 3.00(2) no . . C6 H1 3.30(2) no . . C6 H2 3.289(16) no . . C6 H4 3.282(18) no . . C4 H3 2.753(16) no . . C7 H3 3.338(19) no . . C3 H3 2.712(16) no . . C3 H4 2.65(2) no . . C10 H1 3.295(19) no . . C10 H9 3.048(16) no . . C12 H2 2.482(18) no . . C12 H8 3.259(19) no . . C12 H6 3.27(2) no . . C12 H10 3.24(2) no . . C12 H11 2.53(3) no . . C12 H13 3.52(2) no . . C12 H12 2.93(2) no . . C1 H4 2.69(3) no . . C13 H2 2.703(15) no . . C13 H5 3.246(18) no . . C13 H7 3.24(2) no . . C13 H11 3.60(2) no . . C13 H12 3.02(3) no . . C14 H2 3.571(15) no . . C14 H6 3.256(19) no . . C15 H9 3.264(18) no . . C15 H5 3.27(2) no . . C16 H8 3.242(17) no . . C17 H1 2.616(16) no . . C17 H9 3.49(2) no . . C17 H5 3.119(19) no . . C18 H1 3.013(15) no . . C18 H9 3.35(3) no . . F2 H3 2.473(16) no . . F6 H4 2.40(2) no . . F1 H3 2.651(16) no . . F3 H4 2.36(3) no . . C19 H2 3.249(18) no . . C19 H9 3.268(17) no . . C19 H7 3.25(2) no . . C19 H11 2.84(2) no . . N2 H1 2.494(17) no . . N2 H4 3.25(2) no . . N1 H1 2.674(16) no . . N1 H2 2.57(2) no . . N1 H9 2.641(17) no . . N1 H5 2.571(17) no . . N1 H13 2.692(18) no . . N1 H12 2.722(18) no . . N1 H14 3.31(2) no . . H1 H10 2.16(3) no . . H1 H11 3.51(3) no . . H1 H13 2.54(3) no . . H1 H14 3.48(3) no . . H3 H2 2.33(3) no . . H2 H9 2.83(2) no . . H9 H8 2.34(3) no . . H9 H13 3.29(3) no . . H9 H12 2.86(4) no . . H5 H6 2.38(3) no . . H5 H11 2.65(3) no . . H8 H7 2.31(3) no . . H7 H6 2.32(3) no . . H10 H13 2.42(2) no . . H10 H12 2.87(3) no . . H10 H14 2.36(3) no . . H11 H13 2.85(3) no . . H11 H12 2.36(3) no . . H11 H14 2.38(3) no . . C8 H9 3.015(15) no . 2_566 C2 H2 3.432(13) no . 2_656 C2 H8 3.169(17) no . 2_566 C2 H14 3.57(3) no . 2_666 C9 H9 3.516(16) no . 2_566 C6 H12 3.306(18) no . 2_566 C4 H6 3.319(18) no . 1_554 C11 H13 3.441(15) no . 2_566 C11 H12 3.243(17) no . 2_566 C11 H14 3.47(2) no . 1_545 C7 H9 3.113(14) no . 2_566 C7 H8 3.314(17) no . 2_566 C3 H6 3.569(19) no . 1_554 C3 H10 3.403(14) no . 2_656 C10 H13 3.444(17) no . 2_566 C5 H5 3.473(17) no . 1_554 C5 H5 3.506(17) no . 2_656 C5 H6 3.044(18) no . 1_554 C1 H2 3.577(13) no . 2_656 C1 H5 3.37(2) no . 1_554 C1 H8 3.474(16) no . 2_566 C1 H7 3.28(3) no . 1_654 C1 H14 3.46(2) no . 2_666 C18 H3 3.426(17) no . 1_565 F2 H1 2.853(14) no . 2_656 F2 H8 3.42(2) no . 2_556 F2 H10 2.703(15) no . 2_656 F2 H13 2.75(2) no . 1_545 F2 H14 2.979(17) no . 1_545 F4 H2 2.885(15) no . 2_656 F4 H7 2.87(2) no . 1_654 F4 H11 3.37(2) no . 2_666 F4 H12 3.30(3) no . 2_666 F4 H14 2.76(2) no . 2_666 F6 H4 2.56(2) no . 2_655 F6 H5 2.695(18) no . 1_554 F6 H5 3.139(19) no . 2_656 F6 H7 3.56(3) no . 1_654 F1 H3 3.085(16) no . 2_556 F1 H2 2.71(2) no . 2_556 F1 H6 3.37(2) no . 1_554 F1 H12 2.942(19) no . 2_566 F1 H14 3.239(16) no . 2_566 F5 H5 3.32(3) no . 1_554 F5 H8 2.733(17) no . 2_566 F5 H7 2.75(3) no . 1_654 F5 H7 3.131(16) no . 2_566 F5 H11 2.92(3) no . 2_666 F3 H8 3.03(2) no . 2_556 F3 H7 3.47(3) no . 2_556 F3 H6 3.482(19) no . 1_554 F3 H10 3.199(14) no . 2_656 F3 H11 3.591(15) no . 2_656 C19 H4 3.527(15) no . 2_656 C19 H7 3.57(3) no . 2_567 N2 H3 3.534(14) no . 2_656 N2 H9 3.511(15) no . 2_566 N2 H8 2.711(15) no . 2_566 N2 H10 3.55(2) no . 2_666 N2 H14 2.84(3) no . 2_666 N1 H4 3.570(14) no . 2_656 H1 F2 2.853(14) no . 2_656 H1 H1 3.45(3) no . 2_666 H1 H9 3.15(3) no . 2_566 H1 H8 3.48(3) no . 2_566 H1 H10 3.16(3) no . 2_666 H1 H14 3.25(3) no . 2_666 H3 C18 3.426(17) no . 1_545 H3 F1 3.085(16) no . 2_556 H3 N2 3.534(14) no . 2_656 H3 H3 2.96(3) no . 2_556 H3 H13 3.44(3) no . 1_545 H3 H13 3.56(2) no . 2_566 H3 H12 3.39(2) no . 2_566 H3 H14 2.71(3) no . 1_545 H2 C2 3.432(13) no . 2_656 H2 C1 3.577(13) no . 2_656 H2 F4 2.885(15) no . 2_656 H2 F1 2.71(2) no . 2_556 H2 H13 3.56(3) no . 2_566 H4 F6 2.56(2) no . 2_655 H4 C19 3.527(15) no . 2_656 H4 N1 3.570(14) no . 2_656 H4 H4 3.51(3) no . 2_655 H4 H5 3.03(3) no . 1_554 H4 H5 2.81(3) no . 2_656 H4 H6 3.00(3) no . 1_554 H9 C8 3.015(15) no . 2_566 H9 C9 3.516(16) no . 2_566 H9 C7 3.113(14) no . 2_566 H9 N2 3.511(15) no . 2_566 H9 H1 3.15(3) no . 2_566 H9 H13 2.96(3) no . 2_566 H5 C5 3.473(17) no . 1_556 H5 C5 3.506(17) no . 2_656 H5 C1 3.37(2) no . 1_556 H5 F6 2.695(18) no . 1_556 H5 F6 3.139(19) no . 2_656 H5 F5 3.32(3) no . 1_556 H5 H4 3.03(3) no . 1_556 H5 H4 2.81(3) no . 2_656 H5 H7 3.57(3) no . 2_567 H8 C2 3.169(17) no . 2_566 H8 C7 3.314(17) no . 2_566 H8 C1 3.474(16) no . 2_566 H8 F2 3.42(2) no . 2_556 H8 F5 2.733(17) no . 2_566 H8 F3 3.03(2) no . 2_556 H8 N2 2.711(15) no . 2_566 H8 H1 3.48(3) no . 2_566 H8 H10 3.23(3) no . 1_455 H8 H11 3.47(3) no . 1_455 H7 C1 3.28(3) no . 1_456 H7 F4 2.87(2) no . 1_456 H7 F6 3.56(3) no . 1_456 H7 F5 2.75(3) no . 1_456 H7 F5 3.131(16) no . 2_566 H7 F3 3.47(3) no . 2_556 H7 C19 3.57(3) no . 2_567 H7 H5 3.57(3) no . 2_567 H7 H11 3.12(3) no . 2_567 H6 C4 3.319(18) no . 1_556 H6 C3 3.569(19) no . 1_556 H6 C5 3.044(18) no . 1_556 H6 F1 3.37(2) no . 1_556 H6 F3 3.482(19) no . 1_556 H6 H4 3.00(3) no . 1_556 H6 H12 3.46(3) no . 2_567 H10 C3 3.403(14) no . 2_656 H10 F2 2.703(15) no . 2_656 H10 F3 3.199(14) no . 2_656 H10 N2 3.55(2) no . 2_666 H10 H1 3.16(3) no . 2_666 H10 H8 3.23(3) no . 1_655 H11 F4 3.37(2) no . 2_666 H11 F5 2.92(3) no . 2_666 H11 F3 3.591(15) no . 2_656 H11 H8 3.47(3) no . 1_655 H11 H7 3.12(3) no . 2_567 H13 C11 3.441(15) no . 2_566 H13 C10 3.444(17) no . 2_566 H13 F2 2.75(2) no . 1_565 H13 H3 3.44(3) no . 1_565 H13 H3 3.56(2) no . 2_566 H13 H2 3.56(3) no . 2_566 H13 H9 2.96(3) no . 2_566 H12 C6 3.306(18) no . 2_566 H12 C11 3.243(17) no . 2_566 H12 F4 3.30(3) no . 2_666 H12 F1 2.942(19) no . 2_566 H12 H3 3.39(2) no . 2_566 H12 H6 3.46(3) no . 2_567 H14 C2 3.57(3) no . 2_666 H14 C11 3.47(2) no . 1_565 H14 C1 3.46(2) no . 2_666 H14 F2 2.979(17) no . 1_565 H14 F4 2.76(2) no . 2_666 H14 F1 3.239(16) no . 2_566 H14 N2 2.84(3) no . 2_666 H14 H1 3.25(3) no . 2_666 H14 H3 2.71(3) no . 1_565 #============================================================================== #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================