# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Ghosh, Pradyut' _publ_contact_author_email icpg@iacs.res.in _publ_section_title ; Functionalized Guanidinium Chloride Based Colourimetric Sensors for Fluoride and Acetate: Single Crystal X-ray Structural Evidence of -NH Deprotonation and Complexation ; loop_ _publ_author_name P.Ghosh P.Bose N.Ahamed # Attachment 'complex-1.cif' data_Complex-1 _database_code_depnum_ccdc_archive 'CCDC 775864' #TrackingRef 'complex-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H9 F10 N5 O' _chemical_formula_weight 477.28 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.012(10) _cell_length_b 11.932(7) _cell_length_c 19.682(12) _cell_angle_alpha 90.00 _cell_angle_beta 104.571(8) _cell_angle_gamma 90.00 _cell_volume 3639(4) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3201 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 23.90 _exptl_crystal_description NEEDLE _exptl_crystal_colour BROWN _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.742 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1904 _exptl_absorpt_coefficient_mu 0.184 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9436 _exptl_absorpt_correction_T_max 0.9909 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER CCD AREA DETECTOR' _diffrn_measurement_method 'OMEGA SCAN' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23147 _diffrn_reflns_av_R_equivalents 0.0554 _diffrn_reflns_av_sigmaI/netI 0.0507 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 24.39 _reflns_number_total 5944 _reflns_number_gt 3922 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'MERCURY 2.2' _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^)+(0.0515P)^2^+2.3621P] 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 5944 _refine_ls_number_parameters 633 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0815 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1277 _refine_ls_wR_factor_gt 0.1123 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.74300(19) 0.1181(3) 0.43622(16) 0.0254(7) Uani 1 1 d . . . C2 C 0.7678(2) 0.1192(3) 0.50841(17) 0.0283(8) Uani 1 1 d . . . C3 C 0.8550(2) 0.1179(3) 0.54233(16) 0.0274(8) Uani 1 1 d . . . C4 C 0.9148(2) 0.1130(3) 0.50248(16) 0.0268(7) Uani 1 1 d . . . C5 C 0.88885(19) 0.1113(2) 0.43053(16) 0.0237(7) Uani 1 1 d . . . C6 C 0.8010(2) 0.1138(2) 0.39378(16) 0.0230(7) Uani 1 1 d . . . C7 C 0.7691(2) 0.1130(3) 0.31712(16) 0.0251(7) Uani 1 1 d . . . H7 H 0.7103 0.1200 0.2966 0.030 Uiso 1 1 calc R . . N8 N 0.82223(16) 0.1028(2) 0.27816(13) 0.0245(6) Uani 1 1 d . . . N9 N 0.78824(18) 0.1042(2) 0.20670(14) 0.0265(6) Uani 1 1 d . . . H9 H 0.736(3) 0.120(3) 0.189(2) 0.055(13) Uiso 1 1 d . . . C10 C 0.84686(19) 0.1040(3) 0.16685(16) 0.0227(7) Uani 1 1 d . . . N11 N 0.93078(17) 0.0930(2) 0.19947(16) 0.0272(7) Uani 1 1 d . . . H11A H 0.9456(19) 0.089(2) 0.2438(17) 0.019(9) Uiso 1 1 d . . . H11B H 0.960(2) 0.094(3) 0.1684(17) 0.035(10) Uiso 1 1 d . . . N12 N 0.81537(16) 0.1128(2) 0.09731(13) 0.0254(6) Uani 1 1 d . . . N13 N 0.88370(16) 0.1173(2) 0.06544(13) 0.0237(6) Uani 1 1 d . . . C14 C 0.8621(2) 0.1232(2) -0.00199(16) 0.0232(7) Uani 1 1 d . . . H14 H 0.8041 0.1219 -0.0260 0.028 Uiso 1 1 calc R . . C15 C 0.9287(2) 0.1321(2) -0.04145(16) 0.0236(7) Uani 1 1 d . . . C16 C 1.0179(2) 0.1401(3) -0.01135(15) 0.0239(7) Uani 1 1 d . . . C17 C 1.0768(2) 0.1485(3) -0.05141(17) 0.0256(7) Uani 1 1 d . . . C18 C 1.0494(2) 0.1502(3) -0.12393(16) 0.0259(7) Uani 1 1 d . . . C19 C 0.9625(2) 0.1411(3) -0.15580(16) 0.0270(8) Uani 1 1 d . . . C20 C 0.9044(2) 0.1328(3) -0.11496(16) 0.0251(7) Uani 1 1 d . . . C21 C 0.4394(2) 0.8448(3) 0.25107(17) 0.0259(7) Uani 1 1 d . . . C22 C 0.4537(2) 0.8471(3) 0.32323(17) 0.0301(8) Uani 1 1 d . . . C23 C 0.5369(2) 0.8630(3) 0.36405(16) 0.0313(8) Uani 1 1 d . . . C24 C 0.6034(2) 0.8766(3) 0.33176(17) 0.0304(8) Uani 1 1 d . . . C25 C 0.5877(2) 0.8749(3) 0.25960(16) 0.0269(8) Uani 1 1 d . . . C26 C 0.5045(2) 0.8595(2) 0.21583(16) 0.0242(7) Uani 1 1 d . . . C27 C 0.4817(2) 0.8574(2) 0.13914(16) 0.0244(7) Uani 1 1 d . . . H27 H 0.4246 0.8455 0.1148 0.029 Uiso 1 1 calc R . . N28 N 0.53961(16) 0.8719(2) 0.10452(13) 0.0244(6) Uani 1 1 d . . . N29 N 0.51056(18) 0.8654(2) 0.03292(13) 0.0256(6) Uani 1 1 d . . . H29 H 0.456(2) 0.847(3) 0.0118(19) 0.047(12) Uiso 1 1 d . . . C30 C 0.5684(2) 0.8821(3) -0.00627(17) 0.0242(7) Uani 1 1 d . . . N31 N 0.64989(18) 0.9081(2) 0.02766(17) 0.0306(7) Uani 1 1 d . . . H31A H 0.665(2) 0.915(3) 0.0747(18) 0.035(10) Uiso 1 1 d . . . H31B H 0.680(3) 0.919(3) -0.002(2) 0.062(13) Uiso 1 1 d . . . N32 N 0.53919(16) 0.8699(2) -0.07494(13) 0.0250(6) Uani 1 1 d . . . N33 N 0.60480(16) 0.8877(2) -0.10824(14) 0.0265(6) Uani 1 1 d . . . C34 C 0.5812(2) 0.8762(3) -0.17529(16) 0.0243(7) Uani 1 1 d . . . H34 H 0.5239 0.8595 -0.1968 0.029 Uiso 1 1 calc R . . C35 C 0.6432(2) 0.8892(3) -0.21839(16) 0.0237(7) Uani 1 1 d . . . C36 C 0.7329(2) 0.8936(3) -0.19308(16) 0.0262(8) Uani 1 1 d . . . C37 C 0.7877(2) 0.9019(3) -0.23696(17) 0.0286(8) Uani 1 1 d . . . C38 C 0.7545(2) 0.9067(3) -0.30873(17) 0.0304(8) Uani 1 1 d . . . C39 C 0.6664(2) 0.9016(3) -0.33683(16) 0.0279(8) Uani 1 1 d . . . C40 C 0.6130(2) 0.8932(3) -0.29171(16) 0.0259(7) Uani 1 1 d . . . C41 C 0.6239(3) 0.3009(4) 0.1793(2) 0.0406(10) Uani 1 1 d . . . O42 O 0.62031(16) 0.1826(2) 0.16894(13) 0.0402(7) Uani 1 1 d . . . C43 C 0.6776(2) 0.3117(3) -0.0056(2) 0.0350(9) Uani 1 1 d . . . O44 O 0.66239(15) 0.1984(2) 0.00995(13) 0.0351(6) Uani 1 1 d . . . F45 F 0.65691(11) 0.12025(15) 0.40503(9) 0.0322(5) Uani 1 1 d . . . F46 F 0.70855(12) 0.12273(16) 0.54627(10) 0.0397(5) Uani 1 1 d . . . F47 F 0.88123(13) 0.11921(16) 0.61247(9) 0.0390(5) Uani 1 1 d . . . F48 F 0.99991(11) 0.11098(15) 0.53482(9) 0.0338(5) Uani 1 1 d . . . F49 F 0.95173(11) 0.10675(15) 0.39545(9) 0.0301(4) Uani 1 1 d . . . F50 F 1.04911(11) 0.13910(15) 0.05884(9) 0.0299(4) Uani 1 1 d . . . F51 F 1.16182(11) 0.15506(16) -0.02023(9) 0.0335(5) Uani 1 1 d . . . F52 F 1.10799(12) 0.16003(16) -0.16222(10) 0.0369(5) Uani 1 1 d . . . F53 F 0.93524(12) 0.14189(15) -0.22650(9) 0.0349(5) Uani 1 1 d . . . F54 F 0.81923(11) 0.12731(15) -0.14855(9) 0.0330(5) Uani 1 1 d . . . F55 F 0.35687(11) 0.82921(15) 0.21283(9) 0.0321(5) Uani 1 1 d . . . F56 F 0.38722(12) 0.83567(16) 0.35307(10) 0.0401(5) Uani 1 1 d . . . F57 F 0.55256(14) 0.86836(16) 0.43423(9) 0.0446(5) Uani 1 1 d . . . F58 F 0.68486(12) 0.89060(16) 0.37130(10) 0.0408(5) Uani 1 1 d . . . F59 F 0.65624(11) 0.88943(15) 0.23194(9) 0.0346(5) Uani 1 1 d . . . F60 F 0.77013(11) 0.88944(16) -0.12364(9) 0.0363(5) Uani 1 1 d . . . F61 F 0.87407(11) 0.90607(16) -0.21021(10) 0.0375(5) Uani 1 1 d . . . F62 F 0.80894(13) 0.91444(17) -0.35087(10) 0.0444(5) Uani 1 1 d . . . F63 F 0.63320(13) 0.90475(17) -0.40669(9) 0.0437(5) Uani 1 1 d . . . F64 F 0.52655(11) 0.88826(15) -0.32079(9) 0.0324(5) Uani 1 1 d . . . H41A H 0.567(2) 0.333(3) 0.1888(16) 0.036(9) Uiso 1 1 d . . . H41B H 0.638(2) 0.343(3) 0.140(2) 0.057(12) Uiso 1 1 d . . . H41C H 0.669(2) 0.314(3) 0.2173(18) 0.035(10) Uiso 1 1 d . . . H42 H 0.576(3) 0.161(3) 0.138(2) 0.063(14) Uiso 1 1 d . . . H43A H 0.736(2) 0.326(3) -0.0120(16) 0.034(9) Uiso 1 1 d . . . H43B H 0.676(2) 0.360(3) 0.0368(19) 0.053(11) Uiso 1 1 d . . . H43C H 0.636(2) 0.335(3) -0.051(2) 0.053(11) Uiso 1 1 d . . . H44 H 0.699(3) 0.174(4) 0.042(2) 0.076(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 C1 0.0156(17) 0.0254(19) 0.0333(19) 0.0011(15) 0.0028(15) 0.0010(13) C2 0.033(2) 0.0247(19) 0.0298(19) 0.0008(15) 0.0119(16) -0.0012(15) C3 0.036(2) 0.0231(19) 0.0220(18) 0.0005(14) 0.0053(15) -0.0030(15) C4 0.0235(19) 0.0248(19) 0.0269(18) -0.0011(14) -0.0034(15) -0.0019(14) C5 0.0199(17) 0.0212(18) 0.0309(19) -0.0007(14) 0.0079(15) -0.0001(13) C6 0.0265(18) 0.0166(17) 0.0260(17) 0.0015(13) 0.0067(15) 0.0008(13) C7 0.0165(17) 0.0297(19) 0.0278(18) 0.0014(15) 0.0030(14) 0.0014(14) N8 0.0247(15) 0.0265(15) 0.0211(14) -0.0002(11) 0.0036(12) -0.0002(12) N9 0.0189(16) 0.0373(18) 0.0213(15) 0.0006(12) 0.0017(13) 0.0016(13) C10 0.0172(17) 0.0199(18) 0.0300(19) -0.0007(14) 0.0038(15) 0.0015(13) N11 0.0215(17) 0.0364(18) 0.0228(17) 0.0007(13) 0.0039(14) 0.0006(12) N12 0.0194(14) 0.0332(16) 0.0235(15) 0.0013(12) 0.0055(12) 0.0022(12) N13 0.0196(14) 0.0241(15) 0.0268(15) -0.0001(12) 0.0049(12) 0.0006(11) C14 0.0174(17) 0.0226(18) 0.0273(19) -0.0018(14) 0.0012(14) 0.0018(13) C15 0.0244(18) 0.0182(18) 0.0279(18) -0.0012(14) 0.0060(14) -0.0001(13) C16 0.0257(18) 0.0255(19) 0.0195(17) 0.0023(14) 0.0038(14) 0.0041(14) C17 0.0213(18) 0.0222(18) 0.0323(19) -0.0024(14) 0.0050(15) 0.0001(14) C18 0.0309(19) 0.0183(17) 0.0315(19) -0.0008(14) 0.0136(16) -0.0010(14) C19 0.035(2) 0.0232(19) 0.0203(17) 0.0007(14) 0.0023(15) -0.0008(15) C20 0.0221(18) 0.0216(18) 0.0277(18) -0.0014(14) -0.0010(15) 0.0015(14) C21 0.0203(18) 0.0246(18) 0.0312(19) 0.0016(14) 0.0035(15) 0.0023(14) C22 0.037(2) 0.0244(19) 0.032(2) 0.0041(15) 0.0144(17) 0.0071(16) C23 0.048(2) 0.0228(19) 0.0205(18) 0.0001(14) 0.0044(17) 0.0050(16) C24 0.028(2) 0.025(2) 0.0318(19) -0.0001(15) -0.0051(16) 0.0006(15) C25 0.0268(19) 0.0227(19) 0.0298(19) 0.0032(14) 0.0046(15) 0.0022(14) C26 0.0266(18) 0.0187(17) 0.0257(18) -0.0009(14) 0.0033(15) 0.0018(14) C27 0.0222(17) 0.0229(18) 0.0267(18) -0.0013(14) 0.0036(15) 0.0010(14) N28 0.0260(15) 0.0226(15) 0.0236(15) -0.0012(11) 0.0047(12) 0.0008(12) N29 0.0221(16) 0.0327(17) 0.0210(15) -0.0014(12) 0.0036(13) -0.0004(13) C30 0.0198(18) 0.0197(18) 0.0322(19) 0.0009(14) 0.0044(15) 0.0048(13) N31 0.0213(16) 0.0417(19) 0.0284(18) 0.0000(14) 0.0055(14) -0.0026(13) N32 0.0208(14) 0.0285(16) 0.0262(15) 0.0007(12) 0.0067(12) 0.0007(12) N33 0.0236(15) 0.0263(16) 0.0305(16) 0.0004(12) 0.0086(12) 0.0034(12) C34 0.0194(17) 0.0247(19) 0.0280(19) 0.0011(14) 0.0044(14) 0.0021(14) C35 0.0249(18) 0.0210(18) 0.0243(17) -0.0018(14) 0.0046(14) -0.0002(14) C36 0.0259(19) 0.0253(19) 0.0252(18) -0.0010(14) 0.0024(15) 0.0040(14) C37 0.0228(19) 0.028(2) 0.035(2) -0.0033(15) 0.0064(16) 0.0010(14) C38 0.035(2) 0.026(2) 0.034(2) -0.0024(15) 0.0153(17) -0.0024(15) C39 0.040(2) 0.0248(19) 0.0190(17) -0.0017(14) 0.0071(15) -0.0016(15) C40 0.0240(18) 0.0213(18) 0.0294(19) 0.0001(14) 0.0014(15) -0.0011(14) C41 0.032(2) 0.060(3) 0.026(2) 0.004(2) 0.0022(19) 0.004(2) O42 0.0220(14) 0.061(2) 0.0338(15) -0.0045(13) 0.0004(12) 0.0003(13) C43 0.029(2) 0.042(2) 0.033(2) 0.0058(18) 0.0066(18) -0.0011(17) O44 0.0216(13) 0.0427(16) 0.0363(15) 0.0106(12) -0.0015(12) -0.0020(11) F45 0.0214(10) 0.0387(12) 0.0375(11) -0.0006(9) 0.0092(9) 0.0001(8) F46 0.0422(12) 0.0459(13) 0.0381(12) -0.0005(9) 0.0233(10) -0.0019(10) F47 0.0520(13) 0.0384(12) 0.0245(11) 0.0025(9) 0.0058(9) -0.0039(10) F48 0.0280(11) 0.0353(11) 0.0322(11) 0.0012(9) -0.0036(9) -0.0004(9) F49 0.0222(10) 0.0379(11) 0.0307(10) 0.0010(8) 0.0074(8) -0.0001(8) F50 0.0243(10) 0.0418(12) 0.0218(10) -0.0010(8) 0.0024(8) 0.0002(8) F51 0.0205(10) 0.0432(12) 0.0364(11) -0.0014(9) 0.0063(9) -0.0014(8) F52 0.0396(11) 0.0402(12) 0.0373(11) -0.0001(9) 0.0217(9) -0.0030(9) F53 0.0427(12) 0.0388(12) 0.0214(10) 0.0020(8) 0.0048(9) 0.0014(9) F54 0.0241(11) 0.0425(12) 0.0280(10) 0.0001(9) -0.0016(8) -0.0001(9) F55 0.0206(10) 0.0403(12) 0.0340(11) 0.0018(9) 0.0040(8) -0.0015(8) F56 0.0437(12) 0.0464(13) 0.0364(11) 0.0055(9) 0.0216(10) 0.0091(10) F57 0.0655(15) 0.0391(13) 0.0259(11) -0.0009(9) 0.0055(10) 0.0075(10) F58 0.0357(12) 0.0397(12) 0.0365(11) -0.0018(9) -0.0105(10) -0.0024(9) F59 0.0202(10) 0.0449(12) 0.0367(11) -0.0005(9) 0.0033(9) -0.0042(9) F60 0.0253(10) 0.0558(13) 0.0260(10) 0.0016(9) 0.0028(9) -0.0005(9) F61 0.0226(11) 0.0475(13) 0.0430(12) -0.0006(10) 0.0093(9) -0.0011(9) F62 0.0478(13) 0.0517(14) 0.0416(12) -0.0030(10) 0.0257(11) -0.0077(10) F63 0.0551(14) 0.0497(14) 0.0239(11) -0.0002(9) 0.0053(10) -0.0094(10) F64 0.0251(11) 0.0335(11) 0.0331(11) -0.0013(9) -0.0031(8) -0.0012(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 F45 1.361(3) . ? C1 C2 1.376(4) . ? C1 C6 1.398(4) . ? C2 F46 1.346(3) . ? C2 C3 1.388(5) . ? C3 F47 1.338(4) . ? C3 C4 1.384(4) . ? C4 F48 1.351(4) . ? C4 C5 1.372(4) . ? C5 F49 1.358(3) . ? C5 C6 1.410(4) . ? C6 C7 1.466(4) . ? C7 N8 1.286(4) . ? C7 H7 0.9300 . ? N8 N9 1.374(4) . ? N9 C10 1.366(4) . ? N9 H9 0.84(4) . ? C10 N12 1.339(4) 1 ? C10 N12 1.339(4) . ? C10 N11 1.342(4) . ? N11 H11A 0.85(3) . ? N11 H11B 0.86(3) . ? N12 N13 1.392(3) . ? N13 C14 1.286(4) . ? N13 N12 1.392(3) 1 ? C14 C15 1.472(4) . ? C14 H14 0.9300 . ? C15 C20 1.400(4) . ? C15 C16 1.405(4) . ? C16 F50 1.346(3) . ? C16 C17 1.377(4) . ? C17 F51 1.348(4) . ? C17 C18 1.384(4) . ? C18 F52 1.348(3) . ? C18 C19 1.379(4) . ? C19 F53 1.349(3) . ? C19 C20 1.378(4) . ? C20 F54 1.359(4) . ? C21 F55 1.359(4) . ? C21 C22 1.381(4) . ? C21 C26 1.400(4) . ? C22 F56 1.346(4) . ? C22 C23 1.385(5) . ? C23 F57 1.342(4) . ? C23 C24 1.380(5) . ? C24 F58 1.350(4) . ? C24 C25 1.379(5) . ? C25 F59 1.353(4) . ? C25 C26 1.405(4) . ? C26 C27 1.461(4) . ? C27 N28 1.293(4) . ? C27 H27 0.9300 . ? N28 N29 1.371(4) . ? N29 C30 1.361(4) . ? N29 H29 0.89(4) . ? C30 N32 1.322(4) . ? C30 N31 1.344(4) . ? N31 H31A 0.90(3) . ? N31 H31B 0.86(4) . ? N32 N33 1.387(3) . ? N33 C34 1.285(4) . ? C34 C35 1.467(4) . ? C34 H34 0.9300 . ? C35 C36 1.398(4) . ? C35 C40 1.403(4) . ? C36 F60 1.348(3) . ? C36 C37 1.381(4) . ? C37 F61 1.351(4) . ? C37 C38 1.380(5) . ? C38 F62 1.349(3) . ? C38 C39 1.382(5) . ? C39 F63 1.344(4) . ? C39 C40 1.382(4) . ? C40 F64 1.360(4) . ? C41 O42 1.425(5) 1 ? C41 O42 1.425(5) . ? C41 H41A 1.04(3) . ? C41 H41B 1.00(4) . ? C41 H41C 0.92(3) . ? O42 H42 0.85(4) . ? C43 O44 1.420(4) . ? C43 H43A 0.99(3) . ? C43 H43B 1.02(4) . ? C43 H43C 1.01(4) . ? O44 H44 0.80(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F45 C1 C2 117.5(3) . . ? F45 C1 C6 118.8(3) . . ? C2 C1 C6 123.7(3) . . ? F46 C2 C1 120.8(3) . . ? F46 C2 C3 119.8(3) . . ? C1 C2 C3 119.4(3) . . ? F47 C3 C4 120.2(3) . . ? F47 C3 C2 120.9(3) . . ? C4 C3 C2 119.0(3) . . ? F48 C4 C5 119.6(3) . . ? F48 C4 C3 119.6(3) . . ? C5 C4 C3 120.8(3) . . ? F49 C5 C4 117.0(3) . . ? F49 C5 C6 120.7(3) . . ? C4 C5 C6 122.2(3) . . ? C1 C6 C5 114.9(3) . . ? C1 C6 C7 120.2(3) . . ? C5 C6 C7 124.9(3) . . ? N8 C7 C6 120.2(3) . . ? N8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 N8 N9 117.3(3) . . ? C10 N9 N8 115.8(3) . . ? C10 N9 H9 121(3) . . ? N8 N9 H9 122(3) . . ? N12 C10 N11 124.8(3) 1 . ? N12 C10 N11 124.8(3) . . ? N12 C10 N9 116.8(3) 1 . ? N12 C10 N9 116.8(3) . . ? N11 C10 N9 118.4(3) . . ? C10 N11 H11A 119(2) . . ? C10 N11 H11B 109(2) . . ? H11A N11 H11B 132(3) . . ? C10 N12 N13 109.1(2) . . ? C14 N13 N12 115.4(3) . 1 ? C14 N13 N12 115.4(3) . . ? N13 C14 C15 120.4(3) . . ? N13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C20 C15 C16 115.1(3) . . ? C20 C15 C14 119.7(3) . . ? C16 C15 C14 125.2(3) . . ? F50 C16 C17 117.2(3) . . ? F50 C16 C15 120.6(3) . . ? C17 C16 C15 122.2(3) . . ? F51 C17 C16 120.2(3) . . ? F51 C17 C18 119.4(3) . . ? C16 C17 C18 120.5(3) . . ? F52 C18 C19 121.1(3) . . ? F52 C18 C17 119.6(3) . . ? C19 C18 C17 119.3(3) . . ? F53 C19 C20 120.8(3) . . ? F53 C19 C18 119.7(3) . . ? C20 C19 C18 119.5(3) . . ? F54 C20 C19 117.5(3) . . ? F54 C20 C15 119.1(3) . . ? C19 C20 C15 123.4(3) . . ? F55 C21 C22 117.3(3) . . ? F55 C21 C26 118.9(3) . . ? C22 C21 C26 123.7(3) . . ? F56 C22 C21 120.1(3) . . ? F56 C22 C23 120.8(3) . . ? C21 C22 C23 119.1(3) . . ? F57 C23 C24 120.2(3) . . ? F57 C23 C22 120.5(3) . . ? C24 C23 C22 119.3(3) . . ? F58 C24 C25 119.7(3) . . ? F58 C24 C23 119.6(3) . . ? C25 C24 C23 120.7(3) . . ? F59 C25 C24 117.1(3) . . ? F59 C25 C26 120.7(3) . . ? C24 C25 C26 122.2(3) . . ? C21 C26 C25 114.9(3) . . ? C21 C26 C27 119.1(3) . . ? C25 C26 C27 126.0(3) . . ? N28 C27 C26 121.1(3) . . ? N28 C27 H27 119.5 . . ? C26 C27 H27 119.5 . . ? C27 N28 N29 115.5(3) . . ? C30 N29 N28 118.1(3) . . ? C30 N29 H29 120(2) . . ? N28 N29 H29 122(2) . . ? N32 C30 N31 125.6(3) . . ? N32 C30 N29 116.6(3) . . ? N31 C30 N29 117.8(3) . . ? C30 N31 H31A 121(2) . . ? C30 N31 H31B 110(3) . . ? H31A N31 H31B 129(3) . . ? C30 N32 N33 110.5(3) . . ? C34 N33 N32 114.0(3) . . ? N33 C34 C35 121.0(3) . . ? N33 C34 H34 119.5 . . ? C35 C34 H34 119.5 . . ? C36 C35 C40 115.0(3) . . ? C36 C35 C34 125.6(3) . . ? C40 C35 C34 119.4(3) . . ? F60 C36 C37 116.7(3) . . ? F60 C36 C35 120.8(3) . . ? C37 C36 C35 122.5(3) . . ? F61 C37 C38 119.4(3) . . ? F61 C37 C36 120.5(3) . . ? C38 C37 C36 120.1(3) . . ? F62 C38 C37 119.4(3) . . ? F62 C38 C39 120.7(3) . . ? C37 C38 C39 120.0(3) . . ? F63 C39 C40 120.7(3) . . ? F63 C39 C38 120.6(3) . . ? C40 C39 C38 118.7(3) . . ? F64 C40 C39 117.5(3) . . ? F64 C40 C35 118.8(3) . . ? C39 C40 C35 123.7(3) . . ? O42 C41 H41A 112.4(18) 1 . ? O42 C41 H41A 112.4(18) . . ? O42 C41 H41B 113(2) 1 . ? O42 C41 H41B 113(2) . . ? H41A C41 H41B 110(3) . . ? O42 C41 H41C 106(2) 1 . ? O42 C41 H41C 106(2) . . ? H41A C41 H41C 110(3) . . ? H41B C41 H41C 105(3) . . ? C41 O42 H42 114(3) . . ? O44 C43 H43A 114.3(19) . . ? O44 C43 H43B 109(2) . . ? H43A C43 H43B 103(3) . . ? O44 C43 H43C 110(2) . . ? H43A C43 H43C 106(3) . . ? H43B C43 H43C 114(3) . . ? C43 O44 H44 113(3) . . ? 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 N9 H9 O42 0.84(4) 1.95(4) 2.766(4) 165(4) 1 N11 H11B F61 0.86(3) 2.57(3) 3.078(4) 118(3) 3_765 N29 H29 O44 0.89(4) 1.92(4) 2.790(4) 166(3) 3_665 N31 H31B F51 0.86(4) 2.61(4) 3.147(4) 122(3) 3_765 O42 H42 N32 0.85(4) 1.98(4) 2.821(4) 169(4) 3_665 O44 H44 N12 0.80(4) 2.05(5) 2.807(4) 159(4) 1 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 24.39 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.371 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.072 # Attachment 'complex-3.cif' data_complex-3 _database_code_depnum_ccdc_archive 'CCDC 782762' #TrackingRef 'complex-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H31 N5 O4' _chemical_formula_weight 609.67 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca 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 14.5032(10) _cell_length_b 9.6882(7) _cell_length_c 44.522(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6255.7(8) _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 needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2560 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9847 _exptl_absorpt_correction_T_max 0.9983 _exptl_absorpt_process_details sadabs _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 'Bruker Apex II' _diffrn_measurement_method 'Omega scan' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 55819 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -52 _diffrn_reflns_limit_l_max 52 _diffrn_reflns_theta_min 0.91 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5518 _reflns_number_gt 4635 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II' _computing_cell_refinement 'Bruker Apex II' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury 2.3' _computing_publication_material Shelxl-97 _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^)+(0.0855P)^2^+13.3303P] 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 constrn _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0003(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5518 _refine_ls_number_parameters 417 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1005 _refine_ls_R_factor_gt 0.0879 _refine_ls_wR_factor_ref 0.2407 _refine_ls_wR_factor_gt 0.2308 _refine_ls_goodness_of_fit_ref 1.161 _refine_ls_restrained_S_all 1.161 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5499(3) 0.3849(5) 0.20264(9) 0.0467(10) Uani 1 1 d . . . H1 H 0.5265 0.4481 0.1889 0.056 Uiso 1 1 calc R . . C2 C 0.4907(3) 0.2951(5) 0.21710(10) 0.0528(11) Uani 1 1 d . . . H2 H 0.4279 0.2987 0.2129 0.063 Uiso 1 1 calc R . . C3 C 0.5235(3) 0.1993(5) 0.23783(9) 0.0485(10) Uani 1 1 d . . . H3 H 0.4827 0.1397 0.2474 0.058 Uiso 1 1 calc R . . C4 C 0.6152(3) 0.1929(4) 0.24406(9) 0.0458(10) Uani 1 1 d . . . H4 H 0.6367 0.1290 0.2580 0.055 Uiso 1 1 calc R . . C5 C 0.6785(3) 0.2826(4) 0.22954(8) 0.0355(8) Uani 1 1 d . . . C6 C 0.6451(3) 0.3817(4) 0.20851(8) 0.0384(9) Uani 1 1 d . . . C7 C 0.7104(3) 0.4703(4) 0.19385(8) 0.0368(8) Uani 1 1 d . . . C8 C 0.8026(3) 0.4551(4) 0.19963(9) 0.0388(9) Uani 1 1 d . . . H8 H 0.8447 0.5120 0.1899 0.047 Uiso 1 1 calc R . . C9 C 0.8348(3) 0.3550(4) 0.21996(9) 0.0431(9) Uani 1 1 d . . . H9 H 0.8977 0.3456 0.2234 0.052 Uiso 1 1 calc R . . C10 C 0.7740(3) 0.2719(4) 0.23467(9) 0.0419(9) Uani 1 1 d . . . H10 H 0.7959 0.2071 0.2483 0.050 Uiso 1 1 calc R . . C11 C 0.6790(3) 0.5781(4) 0.17309(8) 0.0375(9) Uani 1 1 d . . . H11 H 0.6162 0.5952 0.1709 0.045 Uiso 1 1 calc R . . C12 C 0.7572(3) 0.8277(4) 0.12410(8) 0.0349(8) Uani 1 1 d . . . C13 C 0.7277(4) 1.0936(4) 0.07391(9) 0.0535(12) Uani 1 1 d . . . H13 H 0.6636 1.0975 0.0744 0.064 Uiso 1 1 calc R . . C14 C 0.7831(4) 1.1910(5) 0.05422(10) 0.0662(14) Uani 1 1 d . . . C15 C 0.8808(3) 1.1993(5) 0.05739(10) 0.0539(11) Uani 1 1 d . . . H15 H 0.9106 1.1435 0.0713 0.065 Uiso 1 1 calc R . . C16 C 0.9318(6) 1.2896(7) 0.03994(16) 0.107(3) Uani 1 1 d . . . H16 H 0.9955 1.2927 0.0421 0.129 Uiso 1 1 calc R . . C17 C 0.8884(7) 1.3776(7) 0.01873(14) 0.094(2) Uani 1 1 d . . . H17 H 0.9221 1.4388 0.0070 0.113 Uiso 1 1 calc R . . C18 C 0.7928(6) 1.3677(5) 0.01634(11) 0.078(2) Uani 1 1 d . . . C19 C 0.7359(4) 1.2727(6) 0.03462(12) 0.0711(15) Uani 1 1 d . . . C20 C 0.6421(4) 1.2718(4) 0.03098(10) 0.0565(12) Uani 1 1 d . . . H20 H 0.6050 1.2122 0.0420 0.068 Uiso 1 1 calc R . . C21 C 0.6043(7) 1.3618(6) 0.01041(13) 0.107(3) Uani 1 1 d . . . H21 H 0.5405 1.3601 0.0082 0.128 Uiso 1 1 calc R . . C22 C 0.6513(7) 1.4526(6) -0.00693(13) 0.098(2) Uani 1 1 d . . . H22 H 0.6221 1.5116 -0.0204 0.118 Uiso 1 1 calc R . . C23 C 0.7457(6) 1.4512(7) -0.00319(14) 0.0869(18) Uani 1 1 d . . . H23 H 0.7802 1.5118 -0.0149 0.104 Uiso 1 1 calc R . . C24 C 0.2804(3) 0.4770(4) 0.10112(10) 0.0477(10) Uani 1 1 d . . . H24 H 0.2558 0.5451 0.1135 0.057 Uiso 1 1 calc R . . C25 C 0.3748(3) 0.4619(4) 0.09876(9) 0.0402(9) Uani 1 1 d . . . C26 C 0.4112(4) 0.3599(5) 0.08021(10) 0.0583(12) Uani 1 1 d . . . H26 H 0.4747 0.3489 0.0784 0.070 Uiso 1 1 calc R . . C27 C 0.3515(5) 0.2747(5) 0.06436(12) 0.0739(16) Uani 1 1 d . . . H27 H 0.3752 0.2056 0.0521 0.089 Uiso 1 1 calc R . . C28 C 0.2571(5) 0.2916(6) 0.06666(12) 0.0745(16) Uani 1 1 d . . . H28 H 0.2175 0.2355 0.0557 0.089 Uiso 1 1 calc R . . C29 C 0.2224(4) 0.3911(5) 0.08515(11) 0.0626(13) Uani 1 1 d . . . H29 H 0.1589 0.4012 0.0870 0.075 Uiso 1 1 calc R . . C30 C 0.4238(2) 0.0235(4) 0.15892(9) 0.0361(8) Uani 1 1 d . . . C31 C 0.3805(3) -0.0437(4) 0.18228(9) 0.0422(9) Uani 1 1 d . . . H31 H 0.4037 -0.1273 0.1892 0.051 Uiso 1 1 calc R . . C32 C 0.3026(3) 0.0122(4) 0.19548(10) 0.0457(10) Uani 1 1 d . . . H32 H 0.2736 -0.0335 0.2112 0.055 Uiso 1 1 calc R . . C33 C 0.2681(3) 0.1368(4) 0.18513(9) 0.0457(10) Uani 1 1 d . . . H33 H 0.2151 0.1739 0.1937 0.055 Uiso 1 1 calc R . . C34 C 0.3121(3) 0.2058(4) 0.16219(9) 0.0454(10) Uani 1 1 d . . . H34 H 0.2888 0.2895 0.1554 0.054 Uiso 1 1 calc R . . C35 C 0.3906(3) 0.1510(4) 0.14930(9) 0.0398(9) Uani 1 1 d . . . H35 H 0.4212 0.1992 0.1342 0.048 Uiso 1 1 calc R . . C36 C 0.5058(3) -0.0379(4) 0.14386(9) 0.0384(9) Uani 1 1 d . . . C37 C 0.4389(3) 0.5512(4) 0.11611(8) 0.0364(8) Uani 1 1 d . . . N1 N 0.7719(2) 1.0065(3) 0.08969(7) 0.0447(8) Uani 1 1 d . . . N2 N 0.7171(2) 0.9285(3) 0.10817(7) 0.0394(7) Uani 1 1 d . . . H2A H 0.6588 0.9438 0.1095 0.047 Uiso 1 1 calc R . . N3 N 0.8457(2) 0.8069(3) 0.12347(7) 0.0403(8) Uani 1 1 d . . . H3A H 0.8694 0.7398 0.1335 0.048 Uiso 1 1 calc R . . H3B H 0.8806 0.8603 0.1130 0.048 Uiso 1 1 calc R . . N4 N 0.6998(2) 0.7486(3) 0.13986(7) 0.0361(7) Uani 1 1 d . . . H4A H 0.6411 0.7600 0.1387 0.043 Uiso 1 1 calc R . . N5 N 0.7370(2) 0.6484(3) 0.15795(7) 0.0350(7) Uani 1 1 d . . . O1 O 0.55668(19) 0.0384(3) 0.12824(7) 0.0460(7) Uani 1 1 d . . . O2 O 0.52104(18) -0.1667(3) 0.14759(7) 0.0456(7) Uani 1 1 d . . . O3 O 0.39937(18) 0.6576(3) 0.12867(7) 0.0494(8) Uani 1 1 d . . . H3X H 0.4390 0.7098 0.1353 0.074 Uiso 1 1 calc R . . O4 O 0.52065(19) 0.5283(3) 0.11844(7) 0.0511(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.046(2) 0.050(2) 0.044(2) -0.0065(19) -0.0057(18) 0.0035(19) C2 0.037(2) 0.070(3) 0.051(2) -0.005(2) 0.0048(19) -0.008(2) C3 0.041(2) 0.052(2) 0.053(2) -0.010(2) 0.0061(18) -0.0044(19) C4 0.053(2) 0.040(2) 0.045(2) -0.0113(18) -0.0001(19) 0.0010(19) C5 0.040(2) 0.0300(18) 0.0365(19) -0.0135(15) -0.0041(15) 0.0033(16) C6 0.040(2) 0.0366(19) 0.0383(19) -0.0163(16) -0.0012(16) 0.0039(16) C7 0.044(2) 0.0275(18) 0.0394(19) -0.0141(15) 0.0012(16) 0.0018(16) C8 0.039(2) 0.0303(19) 0.047(2) -0.0117(16) -0.0058(17) -0.0002(16) C9 0.038(2) 0.036(2) 0.055(2) -0.0112(18) -0.0085(18) 0.0038(17) C10 0.044(2) 0.035(2) 0.047(2) -0.0110(17) -0.0055(17) 0.0038(18) C11 0.0315(19) 0.0337(19) 0.047(2) -0.0154(17) -0.0016(16) 0.0007(16) C12 0.0374(19) 0.0271(18) 0.0401(19) -0.0160(15) -0.0007(16) -0.0046(15) C13 0.085(3) 0.036(2) 0.040(2) -0.0185(19) 0.010(2) -0.007(2) C14 0.101(4) 0.052(3) 0.046(2) -0.024(2) -0.005(3) 0.017(3) C15 0.062(3) 0.049(2) 0.051(2) -0.006(2) 0.009(2) 0.000(2) C16 0.134(6) 0.088(5) 0.100(5) -0.034(4) 0.056(5) -0.029(5) C17 0.154(7) 0.069(4) 0.060(3) -0.008(3) -0.001(4) 0.030(4) C18 0.154(6) 0.038(3) 0.043(3) -0.014(2) 0.028(3) -0.010(3) C19 0.089(4) 0.061(3) 0.063(3) -0.038(3) -0.006(3) 0.015(3) C20 0.083(4) 0.039(2) 0.047(2) -0.0098(19) -0.002(2) 0.004(2) C21 0.216(9) 0.044(3) 0.061(3) -0.006(3) -0.014(4) 0.017(4) C22 0.180(8) 0.058(3) 0.056(3) -0.006(3) -0.011(4) 0.028(4) C23 0.109(5) 0.081(4) 0.071(4) -0.035(3) 0.009(4) 0.006(4) C24 0.049(2) 0.040(2) 0.054(2) -0.0010(19) 0.0012(19) -0.0120(19) C25 0.051(2) 0.0268(18) 0.043(2) 0.0035(16) -0.0007(18) -0.0020(17) C26 0.072(3) 0.048(2) 0.055(3) -0.008(2) 0.002(2) 0.005(2) C27 0.107(5) 0.056(3) 0.058(3) -0.022(2) -0.002(3) -0.004(3) C28 0.099(4) 0.061(3) 0.064(3) -0.007(3) -0.012(3) -0.032(3) C29 0.068(3) 0.057(3) 0.063(3) -0.001(2) -0.007(2) -0.024(2) C30 0.0314(18) 0.0288(18) 0.048(2) -0.0061(16) -0.0086(16) -0.0018(15) C31 0.037(2) 0.0234(17) 0.066(3) 0.0028(17) -0.0028(19) 0.0004(16) C32 0.045(2) 0.033(2) 0.059(3) 0.0015(18) 0.0046(19) -0.0008(17) C33 0.041(2) 0.041(2) 0.055(2) -0.0057(19) -0.0012(18) 0.0078(18) C34 0.052(2) 0.038(2) 0.046(2) 0.0020(18) -0.0048(19) 0.0123(19) C35 0.043(2) 0.0331(19) 0.043(2) 0.0003(16) -0.0020(17) 0.0033(17) C36 0.0340(19) 0.0278(18) 0.054(2) -0.0078(17) -0.0085(17) -0.0039(16) C37 0.039(2) 0.0262(17) 0.044(2) 0.0035(16) 0.0018(16) -0.0002(16) N1 0.059(2) 0.0324(17) 0.0423(18) -0.0139(15) 0.0077(16) -0.0089(16) N2 0.0405(17) 0.0351(17) 0.0425(17) -0.0108(14) 0.0008(14) -0.0043(14) N3 0.0361(17) 0.0299(15) 0.0550(19) -0.0088(14) 0.0044(14) -0.0018(13) N4 0.0288(15) 0.0334(16) 0.0460(17) -0.0109(14) -0.0013(13) -0.0017(13) N5 0.0350(17) 0.0282(15) 0.0417(16) -0.0113(13) -0.0032(13) 0.0013(13) O1 0.0417(15) 0.0324(14) 0.0639(18) -0.0017(13) 0.0019(13) -0.0010(12) O2 0.0345(14) 0.0243(13) 0.078(2) -0.0076(13) -0.0041(13) -0.0021(11) O3 0.0318(14) 0.0326(14) 0.084(2) -0.0174(14) -0.0040(14) -0.0008(12) O4 0.0374(16) 0.0430(16) 0.073(2) -0.0090(14) -0.0023(14) 0.0066(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.381(6) . ? C1 C6 1.406(6) . ? C1 H1 0.9300 . ? C2 C3 1.393(6) . ? C2 H2 0.9300 . ? C3 C4 1.360(6) . ? C3 H3 0.9300 . ? C4 C5 1.421(6) . ? C4 H4 0.9300 . ? C5 C10 1.407(5) . ? C5 C6 1.425(5) . ? C6 C7 1.436(5) . ? C7 C8 1.369(5) . ? C7 C11 1.467(5) . ? C8 C9 1.406(6) . ? C8 H8 0.9300 . ? C9 C10 1.361(6) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 N5 1.275(5) . ? C11 H11 0.9300 . ? C12 N3 1.299(5) . ? C12 N4 1.332(5) . ? C12 N2 1.340(5) . ? C13 N1 1.272(6) . ? C13 C14 1.518(7) . ? C13 H13 0.9300 . ? C14 C19 1.363(7) . ? C14 C15 1.427(7) . ? C15 C16 1.384(8) . ? C15 H15 0.9300 . ? C16 C17 1.419(10) . ? C16 H16 0.9300 . ? C17 C18 1.394(10) . ? C17 H17 0.9300 . ? C18 C23 1.370(9) . ? C18 C19 1.480(8) . ? C19 C20 1.370(8) . ? C20 C21 1.378(7) . ? C20 H20 0.9300 . ? C21 C22 1.354(10) . ? C21 H21 0.9300 . ? C22 C23 1.379(10) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 C29 1.380(6) . ? C24 C25 1.382(6) . ? C24 H24 0.9300 . ? C25 C26 1.392(6) . ? C25 C37 1.486(5) . ? C26 C27 1.390(7) . ? C26 H26 0.9300 . ? C27 C28 1.381(9) . ? C27 H27 0.9300 . ? C28 C29 1.364(8) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? C30 C31 1.379(5) . ? C30 C35 1.394(5) . ? C30 C36 1.489(5) . ? C31 C32 1.383(6) . ? C31 H31 0.9300 . ? C32 C33 1.385(6) . ? C32 H32 0.9300 . ? C33 C34 1.378(6) . ? C33 H33 0.9300 . ? C34 C35 1.380(6) . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? C36 O1 1.255(5) . ? C36 O2 1.278(4) . ? C37 O4 1.211(5) . ? C37 O3 1.305(4) . ? N1 N2 1.372(4) . ? N2 H2A 0.8600 . ? N3 H3A 0.8600 . ? N3 H3B 0.8600 . ? N4 N5 1.371(4) . ? N4 H4A 0.8600 . ? O3 H3X 0.8200 . ? 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 C2 C1 C6 120.6(4) . . ? C2 C1 H1 119.7 . . ? C6 C1 H1 119.7 . . ? C1 C2 C3 121.1(4) . . ? C1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? C4 C3 C2 119.9(4) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 120.8(4) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C10 C5 C4 121.2(4) . . ? C10 C5 C6 119.4(4) . . ? C4 C5 C6 119.4(4) . . ? C1 C6 C5 118.1(4) . . ? C1 C6 C7 123.4(4) . . ? C5 C6 C7 118.5(3) . . ? C8 C7 C6 119.6(4) . . ? C8 C7 C11 119.9(4) . . ? C6 C7 C11 120.5(3) . . ? C7 C8 C9 121.3(4) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C10 C9 C8 120.2(4) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C5 121.0(4) . . ? C9 C10 H10 119.5 . . ? C5 C10 H10 119.5 . . ? N5 C11 C7 120.5(3) . . ? N5 C11 H11 119.7 . . ? C7 C11 H11 119.7 . . ? N3 C12 N4 122.7(4) . . ? N3 C12 N2 122.1(4) . . ? N4 C12 N2 115.2(3) . . ? N1 C13 C14 117.6(5) . . ? N1 C13 H13 121.2 . . ? C14 C13 H13 121.2 . . ? C19 C14 C15 122.0(5) . . ? C19 C14 C13 117.7(5) . . ? C15 C14 C13 120.3(5) . . ? C16 C15 C14 120.7(6) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C17 121.1(8) . . ? C15 C16 H16 119.5 . . ? C17 C16 H16 119.5 . . ? C18 C17 C16 116.8(8) . . ? C18 C17 H17 121.6 . . ? C16 C17 H17 121.6 . . ? C23 C18 C17 120.2(6) . . ? C23 C18 C19 116.0(7) . . ? C17 C18 C19 123.7(7) . . ? C14 C19 C20 124.8(6) . . ? C14 C19 C18 115.7(6) . . ? C20 C19 C18 119.5(6) . . ? C19 C20 C21 118.0(6) . . ? C19 C20 H20 121.0 . . ? C21 C20 H20 121.0 . . ? C22 C21 C20 126.2(9) . . ? C22 C21 H21 116.9 . . ? C20 C21 H21 116.9 . . ? C21 C22 C23 115.1(7) . . ? C21 C22 H22 122.4 . . ? C23 C22 H22 122.4 . . ? C18 C23 C22 125.2(7) . . ? C18 C23 H23 117.4 . . ? C22 C23 H23 117.4 . . ? C29 C24 C25 120.1(4) . . ? C29 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C24 C25 C26 119.7(4) . . ? C24 C25 C37 121.3(4) . . ? C26 C25 C37 119.0(4) . . ? C27 C26 C25 119.1(5) . . ? C27 C26 H26 120.4 . . ? C25 C26 H26 120.4 . . ? C28 C27 C26 120.6(5) . . ? C28 C27 H27 119.7 . . ? C26 C27 H27 119.7 . . ? C29 C28 C27 119.6(5) . . ? C29 C28 H28 120.2 . . ? C27 C28 H28 120.2 . . ? C28 C29 C24 120.8(5) . . ? C28 C29 H29 119.6 . . ? C24 C29 H29 119.6 . . ? C31 C30 C35 119.5(4) . . ? C31 C30 C36 121.0(3) . . ? C35 C30 C36 119.5(4) . . ? C30 C31 C32 120.5(3) . . ? C30 C31 H31 119.8 . . ? C32 C31 H31 119.8 . . ? C31 C32 C33 119.7(4) . . ? C31 C32 H32 120.1 . . ? C33 C32 H32 120.1 . . ? C34 C33 C32 120.1(4) . . ? C34 C33 H33 120.0 . . ? C32 C33 H33 120.0 . . ? C33 C34 C35 120.3(4) . . ? C33 C34 H34 119.9 . . ? C35 C34 H34 119.9 . . ? C34 C35 C30 119.9(4) . . ? C34 C35 H35 120.1 . . ? C30 C35 H35 120.1 . . ? O1 C36 O2 123.1(4) . . ? O1 C36 C30 118.9(3) . . ? O2 C36 C30 118.0(3) . . ? O4 C37 O3 122.6(4) . . ? O4 C37 C25 123.4(3) . . ? O3 C37 C25 114.0(3) . . ? C13 N1 N2 113.8(4) . . ? C12 N2 N1 117.8(3) . . ? C12 N2 H2A 121.1 . . ? N1 N2 H2A 121.1 . . ? C12 N3 H3A 120.0 . . ? C12 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C12 N4 N5 118.1(3) . . ? C12 N4 H4A 121.0 . . ? N5 N4 H4A 121.0 . . ? C11 N5 N4 115.4(3) . . ? C37 O3 H3X 109.5 . . ? 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 N3 H3B O4 0.86 2.18 2.899(4) 140.8 8_765 N3 H3A O1 0.86 2.24 2.970(4) 142.7 8_765 O3 H3X O2 0.82 1.77 2.593(4) 175.4 1_565 N4 H4A O2 0.86 1.92 2.741(4) 158.9 1_565 N2 H2A O1 0.86 1.93 2.710(4) 149.9 1_565 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.966 _refine_diff_density_min -0.425 _refine_diff_density_rms 0.063 # Attachment 'complex-2.cif' data_complex-2 _database_code_depnum_ccdc_archive 'CCDC 795757' #TrackingRef 'complex-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H22 F10 N5 O6' _chemical_formula_weight 810.59 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' F F 0.0171 0.0103 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/m ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 6.8654(13) _cell_length_b 34.567(6) _cell_length_c 7.1380(14) _cell_angle_alpha 90.00 _cell_angle_beta 98.565(4) _cell_angle_gamma 90.00 _cell_volume 1675.1(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5284 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 28.59 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 822 _exptl_absorpt_coefficient_mu 0.148 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9782 _exptl_absorpt_correction_T_max 0.9883 _exptl_absorpt_process_details sadabs _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 'Bruker Apex II' _diffrn_measurement_method 'Omega scan' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15838 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -41 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3005 _reflns_number_gt 2607 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II' _computing_cell_refinement 'Bruker Apex II' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury 2.3, ORTEP3v2' _computing_publication_material SHELXTL-97 _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^)+(0.0425P)^2^+0.6593P] 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 constrn _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3005 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0400 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0889 _refine_ls_wR_factor_gt 0.0842 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1625(2) 0.10294(5) 0.8104(2) 0.0189(3) Uani 1 1 d . . . C2 C 0.1147(2) 0.06530(5) 0.7556(2) 0.0207(4) Uani 1 1 d . . . C3 C 0.2595(3) 0.03716(5) 0.7756(2) 0.0218(4) Uani 1 1 d . . . C4 C 0.4501(2) 0.04656(5) 0.8512(2) 0.0202(3) Uani 1 1 d . . . C5 C 0.4941(2) 0.08412(5) 0.9078(2) 0.0181(3) Uani 1 1 d . . . C6 C 0.3535(2) 0.11358(4) 0.8887(2) 0.0168(3) Uani 1 1 d . . . C7 C 0.4118(2) 0.15261(4) 0.9568(2) 0.0174(3) Uani 1 1 d . . . H7 H 0.5086 0.1556 1.0617 0.021 Uiso 1 1 calc R . . N8 N 0.33020(19) 0.18261(4) 0.87257(18) 0.0163(3) Uani 1 1 d . . . N9 N 0.38836(19) 0.21710(4) 0.95847(18) 0.0163(3) Uani 1 1 d . . . H9 H 0.4560 0.2177 1.0700 0.020 Uiso 1 1 calc R . . C10 C 0.3358(3) 0.2500 0.8621(3) 0.0147(4) Uani 1 2 d S . . N11 N 0.2446(3) 0.2500 0.6872(3) 0.0160(4) Uani 1 2 d S . . H11 H 0.2157 0.2285 0.6295 0.019 Uiso 0.50 1 d PR . . C12 C 0.7363(3) 0.2500 0.6082(3) 0.0159(5) Uani 1 2 d S . . C13 C 0.7775(2) 0.21520(4) 0.7061(2) 0.0177(3) Uani 1 1 d . . . H13 H 0.7495 0.1918 0.6434 0.021 Uiso 1 1 calc R . . C14 C 0.8601(2) 0.21524(5) 0.8967(2) 0.0203(4) Uani 1 1 d . . . H14 H 0.8876 0.1919 0.9601 0.024 Uiso 1 1 calc R . . C15 C 0.9016(3) 0.2500 0.9926(3) 0.0200(5) Uani 1 2 d S . . H15 H 0.9567 0.2500 1.1198 0.024 Uiso 1 2 calc SR . . C16 C 0.6499 0.2500 0.4014 0.015 Uani 1 2 d S . . O17 O 0.6135 0.2178 0.3179 0.018 Uani 1 1 d . . . C18 C 0.1610 0.1290 0.3528 0.017 Uani 1 1 d . . . C19 C 0.0810 0.0929 0.2945 0.020 Uani 1 1 d . . . H19 H -0.0536 0.0904 0.2546 0.024 Uiso 1 1 calc R . . C20 C 0.2037(3) 0.06085(5) 0.2967(2) 0.0233(4) Uani 1 1 d . . . H20 H 0.1510 0.0369 0.2571 0.028 Uiso 1 1 calc R . . C21 C 0.4045(3) 0.06447(5) 0.3576(2) 0.0245(4) Uani 1 1 d . . . H21 H 0.4857 0.0429 0.3592 0.029 Uiso 1 1 calc R . . C22 C 0.4847(3) 0.10019(5) 0.4164(2) 0.0233(4) Uani 1 1 d . . . H22 H 0.6192 0.1025 0.4582 0.028 Uiso 1 1 calc R . . C23 C 0.3633(2) 0.13247(5) 0.4125(2) 0.0200(4) Uani 1 1 d . . . H23 H 0.4171 0.1564 0.4498 0.024 Uiso 1 1 calc R . . C24 C 0.0361(2) 0.16430(5) 0.3558(2) 0.0175(3) Uani 1 1 d . . . O25 O 0.10393(17) 0.19641(3) 0.39225(16) 0.0230(3) Uani 1 1 d . . . O26 O -0.15678(16) 0.15741(3) 0.31491(16) 0.0212(3) Uani 1 1 d . . . H26 H -0.2177 0.1776 0.3217 0.032 Uiso 1 1 d R . . F27 F 0.01654(14) 0.12916(3) 0.78813(14) 0.0253(2) Uani 1 1 d . . . F28 F -0.07104(14) 0.05602(3) 0.68054(15) 0.0293(2) Uani 1 1 d . . . F29 F 0.21410(15) 0.00082(3) 0.71716(15) 0.0312(3) Uani 1 1 d . . . F30 F 0.59335(14) 0.01960(3) 0.86434(14) 0.0282(2) Uani 1 1 d . . . F31 F 0.68188(13) 0.09260(3) 0.97975(14) 0.0247(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0216(8) 0.0161(8) 0.0192(8) 0.0018(6) 0.0041(6) 0.0022(6) C2 0.0201(8) 0.0216(9) 0.0201(8) -0.0009(7) 0.0018(7) -0.0049(7) C3 0.0289(9) 0.0149(8) 0.0222(9) -0.0032(7) 0.0063(7) -0.0046(7) C4 0.0249(9) 0.0154(8) 0.0209(8) 0.0017(6) 0.0057(7) 0.0049(7) C5 0.0194(8) 0.0196(8) 0.0148(8) 0.0017(6) 0.0007(6) -0.0015(6) C6 0.0228(8) 0.0146(8) 0.0133(8) 0.0023(6) 0.0041(6) -0.0008(6) C7 0.0176(8) 0.0185(8) 0.0157(8) 0.0010(6) 0.0014(6) -0.0002(6) N8 0.0183(7) 0.0135(6) 0.0175(7) -0.0012(5) 0.0034(5) -0.0018(5) N9 0.0181(7) 0.0140(7) 0.0156(7) -0.0008(5) -0.0016(5) -0.0007(5) C10 0.0105(10) 0.0154(11) 0.0184(11) 0.000 0.0028(8) 0.000 N11 0.0151(9) 0.0153(9) 0.0169(10) 0.000 -0.0001(7) 0.000 C12 0.0092(10) 0.0222(12) 0.0170(11) 0.000 0.0041(8) 0.000 C13 0.0158(8) 0.0189(9) 0.0189(8) -0.0010(6) 0.0042(6) -0.0012(6) C14 0.0180(8) 0.0246(9) 0.0189(8) 0.0052(7) 0.0052(7) 0.0025(7) C15 0.0155(11) 0.0307(13) 0.0140(11) 0.000 0.0030(9) 0.000 C16 0.010 0.017 0.017 0.000 0.003 0.000 O17 0.019 0.016 0.018 -0.001 0.000 0.000 C18 0.021 0.018 0.013 0.001 0.003 0.000 C19 0.020 0.020 0.019 0.000 0.001 0.000 C20 0.0300(10) 0.0175(8) 0.0228(9) -0.0013(7) 0.0053(7) -0.0008(7) C21 0.0279(10) 0.0234(9) 0.0237(9) 0.0030(7) 0.0088(7) 0.0075(7) C22 0.0193(8) 0.0299(10) 0.0209(9) 0.0028(7) 0.0037(7) 0.0007(7) C23 0.0227(9) 0.0209(8) 0.0167(8) 0.0007(6) 0.0035(7) -0.0029(7) C24 0.0217(8) 0.0187(8) 0.0116(7) 0.0009(6) 0.0007(6) -0.0013(7) O25 0.0264(6) 0.0172(6) 0.0239(6) -0.0028(5) -0.0010(5) -0.0024(5) O26 0.0195(6) 0.0169(6) 0.0263(6) -0.0013(5) 0.0007(5) 0.0021(5) F27 0.0201(5) 0.0191(5) 0.0356(6) -0.0006(4) 0.0004(4) 0.0026(4) F28 0.0219(5) 0.0256(5) 0.0392(6) -0.0050(4) 0.0008(4) -0.0068(4) F29 0.0335(6) 0.0155(5) 0.0446(6) -0.0092(4) 0.0059(5) -0.0048(4) F30 0.0283(6) 0.0173(5) 0.0388(6) -0.0017(4) 0.0050(5) 0.0056(4) F31 0.0201(5) 0.0217(5) 0.0304(5) -0.0016(4) -0.0031(4) 0.0011(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 F27 1.3426(18) . ? C1 C2 1.384(2) . ? C1 C6 1.396(2) . ? C2 F28 1.3465(19) . ? C2 C3 1.383(2) . ? C3 F29 1.3456(19) . ? C3 C4 1.378(2) . ? C4 F30 1.3481(18) . ? C4 C5 1.380(2) . ? C5 F31 1.3473(18) . ? C5 C6 1.396(2) . ? C6 C7 1.469(2) . ? C7 N8 1.285(2) . ? C7 H7 0.9300 . ? N8 N9 1.3726(18) . ? N9 C10 1.3501(17) . ? N9 H9 0.8600 . ? C10 N11 1.310(3) . ? C10 N9 1.3501(17) 4_565 ? N11 H11 0.8599 . ? C12 C13 1.3989(19) 4_565 ? C12 C13 1.3989(19) . ? C12 C16 1.506(2) . ? C13 C14 1.394(2) . ? C13 H13 0.9300 . ? C14 C15 1.391(2) . ? C14 H14 0.9300 . ? C15 C14 1.391(2) 4_565 ? C15 H15 0.9300 . ? C16 O17 1.2701 . ? C16 O17 1.2701 4_565 ? C18 C23 1.3962(17) . ? C18 C19 1.4018 . ? C18 C24 1.4928(16) . ? C19 C20 1.3899(17) . ? C19 H19 0.9300 . ? C20 C21 1.388(3) . ? C20 H20 0.9300 . ? C21 C22 1.391(2) . ? C21 H21 0.9300 . ? C22 C23 1.391(2) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 O25 1.2166(19) 1 ? C24 O25 1.2166(19) . ? C24 O26 1.3345(19) . ? O26 H26 0.8201 . ? 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 F27 C1 C2 117.39(14) . . ? F27 C1 C6 120.63(14) . . ? C2 C1 C6 121.97(15) . . ? F28 C2 C3 119.81(14) . . ? F28 C2 C1 120.45(15) . . ? C3 C2 C1 119.74(15) . . ? F29 C3 C4 120.27(15) . . ? F29 C3 C2 119.69(15) . . ? C4 C3 C2 120.03(15) . . ? F30 C4 C3 120.31(14) . . ? F30 C4 C5 120.31(15) . . ? C3 C4 C5 119.35(15) . . ? F31 C5 C4 118.13(14) . . ? F31 C5 C6 119.16(14) . . ? C4 C5 C6 122.69(15) . . ? C5 C6 C1 116.21(14) . . ? C5 C6 C7 119.15(14) . . ? C1 C6 C7 124.60(14) . . ? N8 C7 C6 120.52(14) . . ? N8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 N8 N9 114.49(13) . . ? C10 N9 N8 117.78(13) . . ? C10 N9 H9 121.1 . . ? N8 N9 H9 121.1 . . ? N11 C10 N9 122.61(9) . 4_565 ? N11 C10 N9 122.61(9) . . ? N9 C10 N9 114.76(19) 4_565 . ? C10 N11 H11 120.0 . . ? C13 C12 C13 118.6(2) 4_565 . ? C13 C12 C16 120.68(10) 4_565 . ? C13 C12 C16 120.68(10) . . ? C14 C13 C12 120.61(15) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C13 120.33(15) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C14 119.5(2) . 4_565 ? C14 C15 H15 120.3 . . ? C14 C15 H15 120.3 4_565 . ? O17 C16 O17 122.5 . 4_565 ? O17 C16 C12 118.743(6) . . ? O17 C16 C12 118.743(6) 4_565 . ? C23 C18 C19 119.64(7) . . ? C23 C18 C24 118.23(9) . . ? C19 C18 C24 122.12(6) . . ? C20 C19 C18 119.78(7) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C21 120.22(14) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C20 C21 C22 120.32(15) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C21 C22 C23 119.78(16) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? C22 C23 C18 120.24(14) . . ? C22 C23 H23 119.9 . . ? C18 C23 H23 119.9 . . ? O25 C24 O25 0.00(11) 1 . ? O25 C24 O26 123.04(15) 1 . ? O25 C24 O26 123.04(15) . . ? O25 C24 C18 123.11(13) 1 . ? O25 C24 C18 123.11(13) . . ? O26 C24 C18 113.85(12) . . ? C24 O26 H26 109.4 . . ? 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 F27 C1 C2 F28 1.0(2) . . . . ? C6 C1 C2 F28 180.00(14) . . . . ? F27 C1 C2 C3 180.00(14) . . . . ? C6 C1 C2 C3 -1.0(2) . . . . ? F28 C2 C3 F29 1.0(2) . . . . ? C1 C2 C3 F29 -178.08(14) . . . . ? F28 C2 C3 C4 179.59(15) . . . . ? C1 C2 C3 C4 0.5(2) . . . . ? F29 C3 C4 F30 1.2(2) . . . . ? C2 C3 C4 F30 -177.46(14) . . . . ? F29 C3 C4 C5 179.11(14) . . . . ? C2 C3 C4 C5 0.5(2) . . . . ? F30 C4 C5 F31 -1.5(2) . . . . ? C3 C4 C5 F31 -179.43(14) . . . . ? F30 C4 C5 C6 176.77(14) . . . . ? C3 C4 C5 C6 -1.2(2) . . . . ? F31 C5 C6 C1 179.00(13) . . . . ? C4 C5 C6 C1 0.8(2) . . . . ? F31 C5 C6 C7 -3.2(2) . . . . ? C4 C5 C6 C7 178.58(15) . . . . ? F27 C1 C6 C5 179.31(14) . . . . ? C2 C1 C6 C5 0.3(2) . . . . ? F27 C1 C6 C7 1.6(2) . . . . ? C2 C1 C6 C7 -177.37(15) . . . . ? C5 C6 C7 N8 147.48(15) . . . . ? C1 C6 C7 N8 -34.9(2) . . . . ? C6 C7 N8 N9 175.66(13) . . . . ? C7 N8 N9 C10 168.87(15) . . . . ? N8 N9 C10 N11 -4.8(3) . . . . ? N8 N9 C10 N9 176.57(11) . . . 4_565 ? C13 C12 C13 C14 -0.8(3) 4_565 . . . ? C16 C12 C13 C14 179.07(14) . . . . ? C12 C13 C14 C15 0.4(3) . . . . ? C13 C14 C15 C14 0.0(3) . . . 4_565 ? C13 C12 C16 O17 -179.56(13) 4_565 . . . ? C13 C12 C16 O17 0.6(2) . . . . ? C13 C12 C16 O17 -0.6(2) 4_565 . . 4_565 ? C13 C12 C16 O17 179.56(13) . . . 4_565 ? C23 C18 C19 C20 -0.01(11) . . . . ? C24 C18 C19 C20 -179.20(11) . . . . ? C18 C19 C20 C21 0.51(18) . . . . ? C19 C20 C21 C22 -0.2(2) . . . . ? C20 C21 C22 C23 -0.5(2) . . . . ? C21 C22 C23 C18 1.0(2) . . . . ? C19 C18 C23 C22 -0.77(17) . . . . ? C24 C18 C23 C22 178.45(13) . . . . ? C23 C18 C24 O25 6.43(18) . . . 1 ? C19 C18 C24 O25 -174.37(11) . . . 1 ? C23 C18 C24 O25 6.43(18) . . . . ? C19 C18 C24 O25 -174.37(11) . . . . ? C23 C18 C24 O26 -173.54(11) . . . . ? C19 C18 C24 O26 5.67(14) . . . . ? 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 N11 H11 O25 0.86 2.07 2.8623(18) 152.3 1 N9 H9 O17 0.86 1.93 2.7916(14) 178.1 1_556 O26 H26 O17 0.82 1.81 2.6179(11) 170.6 1_455 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.325 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.045