# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Kilian Muniz' _publ_contact_author_email MUNIZ@CHIMIE.U-STRASBG.FR loop_ _publ_author_name K.Muniz L.Brelot C.Hovelmann J.Streuff data_streuff1 _database_code_depnum_ccdc_archive 'CCDC 671505' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C35 H33 N3 O4' _chemical_formula_sum 'C35 H33 N3 O4' _chemical_formula_weight 559.64 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9630(5) _cell_length_b 10.0620(5) _cell_length_c 15.7850(5) _cell_angle_alpha 89.717(3) _cell_angle_beta 76.596(3) _cell_angle_gamma 67.802(2) _cell_volume 1419.21(11) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 12846 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _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 9485 _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_sigmaI/netI 0.0462 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6465 _reflns_number_gt 4649 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0594P)^2^+0.2762P] 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 6465 _refine_ls_number_parameters 388 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0755 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1300 _refine_ls_wR_factor_gt 0.1162 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 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 0.31852(17) 0.28205(17) 0.16021(9) 0.0300(3) Uani 1 1 d . . . C2 C 0.3400(2) 0.15041(19) 0.11990(11) 0.0393(4) Uani 1 1 d . . . H2 H 0.4040 0.0639 0.1375 0.047 Uiso 1 1 calc R . . C3 C 0.2706(2) 0.1423(2) 0.05480(12) 0.0460(4) Uani 1 1 d . . . H3 H 0.2873 0.0511 0.0282 0.055 Uiso 1 1 calc R . . C4 C 0.1770(2) 0.2672(2) 0.02845(11) 0.0444(4) Uani 1 1 d . . . H4 H 0.1292 0.2623 -0.0163 0.053 Uiso 1 1 calc R . . C5 C 0.1535(2) 0.3986(2) 0.06764(11) 0.0446(4) Uani 1 1 d . . . H5 H 0.0884 0.4847 0.0502 0.054 Uiso 1 1 calc R . . C6 C 0.22438(19) 0.40650(19) 0.13255(10) 0.0371(4) Uani 1 1 d . . . H6 H 0.2083 0.4981 0.1584 0.044 Uiso 1 1 calc R . . C7 C 0.57106(17) 0.23714(17) 0.17916(9) 0.0279(3) Uani 1 1 d . . . C8 C 0.67257(17) 0.09636(17) 0.17595(10) 0.0324(4) Uani 1 1 d . . . H8 H 0.6405 0.0284 0.2073 0.039 Uiso 1 1 calc R . . C9 C 0.82004(19) 0.0529(2) 0.12777(10) 0.0416(4) Uani 1 1 d . . . H9 H 0.8874 -0.0441 0.1265 0.050 Uiso 1 1 calc R . . C10 C 0.8693(2) 0.1492(2) 0.08189(11) 0.0482(5) Uani 1 1 d . . . H10 H 0.9704 0.1197 0.0494 0.058 Uiso 1 1 calc R . . C11 C 0.7698(2) 0.2890(2) 0.08386(11) 0.0501(5) Uani 1 1 d . . . H11 H 0.8028 0.3561 0.0523 0.060 Uiso 1 1 calc R . . C12 C 0.6218(2) 0.33320(19) 0.13143(10) 0.0388(4) Uani 1 1 d . . . H12 H 0.5545 0.4299 0.1314 0.047 Uiso 1 1 calc R . . C13 C 0.40494(16) 0.28715(15) 0.22864(9) 0.0267(3) Uani 1 1 d . . . C14 C 0.34510(19) 0.43979(16) 0.27638(10) 0.0337(4) Uani 1 1 d . . . H14A H 0.3613 0.5075 0.2333 0.040 Uiso 1 1 calc R . . H14B H 0.2359 0.4718 0.3015 0.040 Uiso 1 1 calc R . . C15 C 0.4201(2) 0.44678(16) 0.34954(10) 0.0345(4) Uani 1 1 d . . . H15A H 0.5278 0.4240 0.3241 0.041 Uiso 1 1 calc R . . H15B H 0.3745 0.5458 0.3790 0.041 Uiso 1 1 calc R . . C16 C 0.40285(18) 0.34102(16) 0.41622(9) 0.0297(3) Uani 1 1 d . . . H16 H 0.2964 0.3748 0.4509 0.036 Uiso 1 1 calc R . . C17 C 0.50705(18) 0.31106(16) 0.47802(10) 0.0317(3) Uani 1 1 d . . . H17A H 0.5747 0.3634 0.4634 0.038 Uiso 1 1 calc R . . H17B H 0.4491 0.3395 0.5397 0.038 Uiso 1 1 calc R . . C18 C 0.55367(16) 0.09349(15) 0.39711(9) 0.0247(3) Uani 1 1 d . A . C19 C 0.38006(17) 0.18633(16) 0.30000(9) 0.0272(3) Uani 1 1 d . . . H19A H 0.2714 0.2121 0.3239 0.033 Uiso 1 1 calc R . . H19B H 0.4251 0.0852 0.2738 0.033 Uiso 1 1 calc R . . C20 C 0.67784(17) 0.07708(16) 0.51693(9) 0.0278(3) Uani 1 1 d . . . C21 C 0.77934(18) 0.11020(19) 0.63340(10) 0.0361(4) Uani 1 1 d . . . H21A H 0.8711 0.1309 0.6173 0.043 Uiso 1 1 calc R . . H21B H 0.8097 0.0042 0.6291 0.043 Uiso 1 1 calc R . . C22 C 0.69592(18) 0.17151(16) 0.72579(9) 0.0299(3) Uani 1 1 d . . . C23 C 0.54152(19) 0.22209(17) 0.75317(10) 0.0350(4) Uani 1 1 d . . . H23 H 0.4841 0.2248 0.7123 0.042 Uiso 1 1 calc R . . C24 C 0.4709(2) 0.2688(2) 0.84053(11) 0.0445(4) Uani 1 1 d . . . H24 H 0.3649 0.3043 0.8592 0.053 Uiso 1 1 calc R . . C25 C 0.5531(2) 0.2643(2) 0.90055(11) 0.0484(5) Uani 1 1 d . . . H25 H 0.5041 0.2948 0.9605 0.058 Uiso 1 1 calc R . . C26 C 0.7065(2) 0.2152(2) 0.87303(11) 0.0473(5) Uani 1 1 d . . . H26 H 0.7634 0.2130 0.9141 0.057 Uiso 1 1 calc R . . C27 C 0.7786(2) 0.16902(18) 0.78587(10) 0.0384(4) Uani 1 1 d . . . H27 H 0.8845 0.1357 0.7673 0.046 Uiso 1 1 calc R . . C28 C 0.74731(18) -0.12997(17) 0.35231(10) 0.0317(3) Uani 1 1 d . A . C29 C 0.9134(10) -0.3756(11) 0.3467(5) 0.0442(16) Uani 0.50 1 d P A 1 H29A H 0.9524 -0.3626 0.3969 0.053 Uiso 0.50 1 calc PR A 1 H29B H 0.9801 -0.3646 0.2924 0.053 Uiso 0.50 1 calc PR A 1 C29B C 0.9043(10) -0.3708(10) 0.3117(5) 0.0532(19) Uani 0.50 1 d P A 2 H29C H 0.9843 -0.3489 0.3280 0.064 Uiso 0.50 1 calc PR A 2 H29D H 0.9181 -0.3705 0.2475 0.064 Uiso 0.50 1 calc PR A 2 C30 C 0.90541(18) -0.51989(18) 0.34265(12) 0.0415(4) Uani 1 1 d . . . C31 C 0.9488(2) -0.5934(2) 0.41199(13) 0.0571(6) Uani 1 1 d . A . H31 H 0.9800 -0.5499 0.4529 0.068 Uiso 1 1 calc R . . C32 C 0.9477(2) -0.7293(3) 0.42287(14) 0.0640(6) Uani 1 1 d . . . H32 H 0.9788 -0.7789 0.4707 0.077 Uiso 1 1 calc R A . C33 C 0.9027(2) -0.7913(2) 0.36599(17) 0.0605(6) Uani 1 1 d . A . H33 H 0.9014 -0.8845 0.3737 0.073 Uiso 1 1 calc R . . C34 C 0.8595(3) -0.7214(3) 0.29789(16) 0.0663(6) Uani 1 1 d . . . H34 H 0.8281 -0.7660 0.2577 0.080 Uiso 1 1 calc R A . C35 C 0.8603(2) -0.5865(2) 0.28598(13) 0.0582(6) Uani 1 1 d . A . H35 H 0.8291 -0.5387 0.2377 0.070 Uiso 1 1 calc R . . O1 O 0.73569(12) -0.05191(11) 0.51434(7) 0.0343(3) Uani 1 1 d . . . O2 O 0.68732(12) 0.17135(11) 0.57329(6) 0.0334(3) Uani 1 1 d . . . O3 O 0.85709(13) -0.10006(12) 0.32985(8) 0.0420(3) Uani 1 1 d . . . O4 O 0.75853(12) -0.26866(12) 0.35699(8) 0.0425(3) Uani 1 1 d . . . N1 N 0.59166(14) 0.15391(13) 0.46261(7) 0.0274(3) Uani 1 1 d . . . N2 N 0.44787(14) 0.19963(13) 0.37024(7) 0.0262(3) Uani 1 1 d . . . N3 N 0.60109(14) -0.04089(13) 0.36750(8) 0.0277(3) 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 0.0276(8) 0.0333(9) 0.0300(7) 0.0082(6) -0.0071(6) -0.0130(7) C2 0.0488(10) 0.0352(10) 0.0436(9) 0.0111(7) -0.0245(8) -0.0193(8) C3 0.0585(12) 0.0478(11) 0.0482(10) 0.0120(8) -0.0269(9) -0.0308(10) C4 0.0467(11) 0.0607(13) 0.0438(9) 0.0209(9) -0.0243(8) -0.0330(10) C5 0.0411(10) 0.0512(12) 0.0460(10) 0.0204(8) -0.0206(8) -0.0174(9) C6 0.0367(9) 0.0351(9) 0.0389(8) 0.0083(7) -0.0134(7) -0.0112(7) C7 0.0344(8) 0.0320(8) 0.0228(7) 0.0027(6) -0.0099(6) -0.0172(7) C8 0.0319(9) 0.0338(9) 0.0296(7) 0.0003(6) -0.0042(6) -0.0125(7) C9 0.0345(9) 0.0470(11) 0.0365(9) -0.0071(7) -0.0029(7) -0.0117(8) C10 0.0376(10) 0.0695(14) 0.0384(9) -0.0073(9) 0.0029(7) -0.0288(10) C11 0.0577(13) 0.0654(14) 0.0397(9) 0.0077(9) -0.0026(8) -0.0429(11) C12 0.0456(10) 0.0396(10) 0.0367(8) 0.0068(7) -0.0087(7) -0.0235(8) C13 0.0280(8) 0.0238(8) 0.0279(7) 0.0041(6) -0.0078(6) -0.0091(6) C14 0.0417(9) 0.0221(8) 0.0329(8) 0.0054(6) -0.0113(7) -0.0065(7) C15 0.0476(10) 0.0202(8) 0.0332(8) 0.0025(6) -0.0121(7) -0.0091(7) C16 0.0326(8) 0.0223(8) 0.0261(7) -0.0013(6) -0.0036(6) -0.0039(6) C17 0.0380(9) 0.0220(8) 0.0282(7) 0.0002(6) -0.0063(6) -0.0051(7) C18 0.0253(7) 0.0226(8) 0.0243(7) 0.0045(5) -0.0023(5) -0.0096(6) C19 0.0262(8) 0.0253(8) 0.0292(7) 0.0042(6) -0.0059(6) -0.0094(6) C20 0.0277(8) 0.0281(9) 0.0242(7) 0.0026(6) -0.0033(6) -0.0089(7) C21 0.0346(9) 0.0386(10) 0.0314(8) 0.0030(7) -0.0130(7) -0.0072(7) C22 0.0382(9) 0.0236(8) 0.0293(7) 0.0047(6) -0.0102(6) -0.0125(7) C23 0.0400(10) 0.0311(9) 0.0355(8) 0.0028(6) -0.0111(7) -0.0146(7) C24 0.0460(11) 0.0422(11) 0.0395(9) 0.0022(7) -0.0017(8) -0.0160(9) C25 0.0690(14) 0.0424(11) 0.0282(8) 0.0022(7) -0.0059(8) -0.0191(10) C26 0.0674(13) 0.0469(11) 0.0339(9) 0.0079(8) -0.0241(9) -0.0224(10) C27 0.0418(10) 0.0391(10) 0.0372(9) 0.0072(7) -0.0166(7) -0.0150(8) C28 0.0315(9) 0.0257(8) 0.0345(8) 0.0010(6) -0.0037(6) -0.0098(7) C29 0.025(2) 0.032(2) 0.065(4) 0.009(3) -0.007(3) -0.0015(17) C29B 0.031(3) 0.023(2) 0.093(6) 0.007(4) -0.002(4) -0.0038(19) C30 0.0252(8) 0.0239(9) 0.0664(12) -0.0045(8) -0.0061(8) -0.0024(7) C31 0.0464(12) 0.0660(15) 0.0513(11) -0.0202(10) -0.0173(9) -0.0103(10) C32 0.0501(13) 0.0693(16) 0.0559(12) 0.0255(11) -0.0086(10) -0.0076(11) C33 0.0362(11) 0.0329(11) 0.0997(18) 0.0064(11) -0.0004(11) -0.0091(9) C34 0.0727(16) 0.0586(15) 0.0758(15) -0.0174(12) -0.0216(12) -0.0323(12) C35 0.0647(14) 0.0632(14) 0.0542(12) 0.0147(10) -0.0304(10) -0.0241(11) O1 0.0381(6) 0.0252(6) 0.0372(6) 0.0038(4) -0.0129(5) -0.0075(5) O2 0.0419(7) 0.0282(6) 0.0280(5) 0.0019(4) -0.0132(5) -0.0087(5) O3 0.0330(7) 0.0321(7) 0.0556(7) 0.0014(5) 0.0008(5) -0.0136(5) O4 0.0276(6) 0.0218(6) 0.0694(8) 0.0016(5) -0.0026(5) -0.0054(5) N1 0.0324(7) 0.0216(7) 0.0250(6) 0.0018(5) -0.0068(5) -0.0072(5) N2 0.0288(7) 0.0204(6) 0.0269(6) 0.0025(5) -0.0061(5) -0.0072(5) N3 0.0281(7) 0.0210(7) 0.0311(6) 0.0023(5) -0.0064(5) -0.0070(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.391(2) . ? C1 C2 1.391(2) . ? C1 C13 1.541(2) . ? C2 C3 1.383(2) . ? C2 H2 0.9500 . ? C3 C4 1.382(3) . ? C3 H3 0.9500 . ? C4 C5 1.376(3) . ? C4 H4 0.9500 . ? C5 C6 1.390(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.388(2) . ? C7 C12 1.394(2) . ? C7 C13 1.542(2) . ? C8 C9 1.389(2) . ? C8 H8 0.9500 . ? C9 C10 1.376(3) . ? C9 H9 0.9500 . ? C10 C11 1.376(3) . ? C10 H10 0.9500 . ? C11 C12 1.389(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.547(2) . ? C13 C19 1.5521(19) . ? C14 C15 1.529(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.521(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 N2 1.4591(19) . ? C16 C17 1.533(2) . ? C16 H16 1.0000 . ? C17 N1 1.4736(19) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 N3 1.3004(18) . ? C18 N2 1.3357(18) . ? C18 N1 1.3940(19) . ? C19 N2 1.4562(18) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 O1 1.2012(18) . ? C20 O2 1.3473(18) . ? C20 N1 1.3796(18) . ? C21 O2 1.4459(17) . ? C21 C22 1.503(2) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.384(2) . ? C22 C27 1.387(2) . ? C23 C24 1.387(2) . ? C23 H23 0.9500 . ? C24 C25 1.378(3) . ? C24 H24 0.9500 . ? C25 C26 1.375(3) . ? C25 H25 0.9500 . ? C26 C27 1.386(2) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? C28 O3 1.2168(19) . ? C28 N3 1.355(2) . ? C28 O4 1.3603(19) . ? C29 O4 1.482(9) . ? C29 C30 1.486(11) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C29B O4 1.441(9) . ? C29B C30 1.572(9) . ? C29B H29C 0.9900 . ? C29B H29D 0.9900 . ? C30 C35 1.368(3) . ? C30 C31 1.379(3) . ? C31 C32 1.381(3) . ? C31 H31 0.9500 . ? C32 C33 1.342(3) . ? C32 H32 0.9500 . ? C33 C34 1.347(3) . ? C33 H33 0.9500 . ? C34 C35 1.372(3) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 117.56(15) . . ? C6 C1 C13 122.15(15) . . ? C2 C1 C13 120.17(13) . . ? C3 C2 C1 121.67(16) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C4 C3 C2 119.92(18) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 119.43(16) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 120.53(16) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C1 120.88(17) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? C8 C7 C12 117.66(15) . . ? C8 C7 C13 122.55(13) . . ? C12 C7 C13 119.69(14) . . ? C7 C8 C9 121.27(15) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C10 C9 C8 120.51(17) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 118.96(17) . . ? C9 C10 H10 120.5 . . ? C11 C10 H10 120.5 . . ? C10 C11 C12 120.94(17) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C11 C12 C7 120.64(17) . . ? C11 C12 H12 119.7 . . ? C7 C12 H12 119.7 . . ? C1 C13 C7 106.62(11) . . ? C1 C13 C14 111.58(12) . . ? C7 C13 C14 111.78(13) . . ? C1 C13 C19 108.88(12) . . ? C7 C13 C19 111.79(11) . . ? C14 C13 C19 106.23(12) . . ? C15 C14 C13 113.16(12) . . ? C15 C14 H14A 108.9 . . ? C13 C14 H14A 108.9 . . ? C15 C14 H14B 108.9 . . ? C13 C14 H14B 108.9 . . ? H14A C14 H14B 107.8 . . ? C16 C15 C14 111.13(13) . . ? C16 C15 H15A 109.4 . . ? C14 C15 H15A 109.4 . . ? C16 C15 H15B 109.4 . . ? C14 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? N2 C16 C15 108.92(12) . . ? N2 C16 C17 102.96(11) . . ? C15 C16 C17 114.83(13) . . ? N2 C16 H16 110.0 . . ? C15 C16 H16 110.0 . . ? C17 C16 H16 110.0 . . ? N1 C17 C16 103.39(12) . . ? N1 C17 H17A 111.1 . . ? C16 C17 H17A 111.1 . . ? N1 C17 H17B 111.1 . . ? C16 C17 H17B 111.1 . . ? H17A C17 H17B 109.0 . . ? N3 C18 N2 123.02(13) . . ? N3 C18 N1 129.27(13) . . ? N2 C18 N1 107.61(12) . . ? N2 C19 C13 110.24(12) . . ? N2 C19 H19A 109.6 . . ? C13 C19 H19A 109.6 . . ? N2 C19 H19B 109.6 . . ? C13 C19 H19B 109.6 . . ? H19A C19 H19B 108.1 . . ? O1 C20 O2 125.54(13) . . ? O1 C20 N1 126.04(14) . . ? O2 C20 N1 108.42(12) . . ? O2 C21 C22 110.89(13) . . ? O2 C21 H21A 109.5 . . ? C22 C21 H21A 109.5 . . ? O2 C21 H21B 109.5 . . ? C22 C21 H21B 109.5 . . ? H21A C21 H21B 108.0 . . ? C23 C22 C27 119.67(14) . . ? C23 C22 C21 122.14(14) . . ? C27 C22 C21 118.09(15) . . ? C22 C23 C24 119.69(15) . . ? C22 C23 H23 120.2 . . ? C24 C23 H23 120.2 . . ? C25 C24 C23 120.69(17) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C26 C25 C24 119.50(16) . . ? C26 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? C25 C26 C27 120.49(16) . . ? C25 C26 H26 119.8 . . ? C27 C26 H26 119.8 . . ? C26 C27 C22 119.95(17) . . ? C26 C27 H27 120.0 . . ? C22 C27 H27 120.0 . . ? O3 C28 N3 128.42(15) . . ? O3 C28 O4 121.95(14) . . ? N3 C28 O4 109.33(13) . . ? O4 C29 C30 106.3(6) . . ? O4 C29 H29A 110.5 . . ? C30 C29 H29A 110.5 . . ? O4 C29 H29B 110.5 . . ? C30 C29 H29B 110.5 . . ? H29A C29 H29B 108.7 . . ? O4 C29B C30 104.0(6) . . ? O4 C29B H29C 111.0 . . ? C30 C29B H29C 111.0 . . ? O4 C29B H29D 111.0 . . ? C30 C29B H29D 111.0 . . ? H29C C29B H29D 109.0 . . ? C35 C30 C31 117.31(18) . . ? C35 C30 C29 132.1(3) . . ? C31 C30 C29 110.6(3) . . ? C35 C30 C29B 110.9(3) . . ? C31 C30 C29B 131.7(3) . . ? C30 C31 C32 120.98(19) . . ? C30 C31 H31 119.5 . . ? C32 C31 H31 119.5 . . ? C33 C32 C31 120.1(2) . . ? C33 C32 H32 120.0 . . ? C31 C32 H32 120.0 . . ? C32 C33 C34 120.0(2) . . ? C32 C33 H33 120.0 . . ? C34 C33 H33 120.0 . . ? C33 C34 C35 120.7(2) . . ? C33 C34 H34 119.7 . . ? C35 C34 H34 119.7 . . ? C30 C35 C34 120.96(19) . . ? C30 C35 H35 119.5 . . ? C34 C35 H35 119.5 . . ? C20 O2 C21 116.37(12) . . ? C28 O4 C29B 112.4(4) . . ? C28 O4 C29 114.2(4) . . ? C20 N1 C18 125.17(12) . . ? C20 N1 C17 122.49(12) . . ? C18 N1 C17 111.54(11) . . ? C18 N2 C19 126.32(12) . . ? C18 N2 C16 114.37(12) . . ? C19 N2 C16 119.28(12) . . ? C18 N3 C28 121.76(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.2(2) . . . . ? C13 C1 C2 C3 -176.39(15) . . . . ? C1 C2 C3 C4 -0.1(3) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C3 C4 C5 C6 0.7(3) . . . . ? C4 C5 C6 C1 -1.0(3) . . . . ? C2 C1 C6 C5 0.7(2) . . . . ? C13 C1 C6 C5 176.84(14) . . . . ? C12 C7 C8 C9 0.8(2) . . . . ? C13 C7 C8 C9 177.20(14) . . . . ? C7 C8 C9 C10 0.1(2) . . . . ? C8 C9 C10 C11 -0.6(3) . . . . ? C9 C10 C11 C12 0.2(3) . . . . ? C10 C11 C12 C7 0.7(3) . . . . ? C8 C7 C12 C11 -1.2(2) . . . . ? C13 C7 C12 C11 -177.72(15) . . . . ? C6 C1 C13 C7 -108.60(16) . . . . ? C2 C1 C13 C7 67.45(17) . . . . ? C6 C1 C13 C14 13.70(19) . . . . ? C2 C1 C13 C14 -170.24(14) . . . . ? C6 C1 C13 C19 130.63(15) . . . . ? C2 C1 C13 C19 -53.32(18) . . . . ? C8 C7 C13 C1 -96.93(16) . . . . ? C12 C7 C13 C1 79.44(16) . . . . ? C8 C7 C13 C14 140.89(14) . . . . ? C12 C7 C13 C14 -42.74(18) . . . . ? C8 C7 C13 C19 21.95(19) . . . . ? C12 C7 C13 C19 -161.68(13) . . . . ? C1 C13 C14 C15 175.70(12) . . . . ? C7 C13 C14 C15 -65.02(16) . . . . ? C19 C13 C14 C15 57.17(17) . . . . ? C13 C14 C15 C16 -56.84(18) . . . . ? C14 C15 C16 N2 49.92(17) . . . . ? C14 C15 C16 C17 164.74(13) . . . . ? N2 C16 C17 N1 -3.34(14) . . . . ? C15 C16 C17 N1 -121.57(13) . . . . ? C1 C13 C19 N2 -174.33(12) . . . . ? C7 C13 C19 N2 68.14(15) . . . . ? C14 C13 C19 N2 -54.04(15) . . . . ? O2 C21 C22 C23 27.5(2) . . . . ? O2 C21 C22 C27 -156.23(14) . . . . ? C27 C22 C23 C24 -0.5(2) . . . . ? C21 C22 C23 C24 175.78(16) . . . . ? C22 C23 C24 C25 -0.6(3) . . . . ? C23 C24 C25 C26 1.2(3) . . . . ? C24 C25 C26 C27 -0.8(3) . . . . ? C25 C26 C27 C22 -0.3(3) . . . . ? C23 C22 C27 C26 0.9(2) . . . . ? C21 C22 C27 C26 -175.53(16) . . . . ? O4 C29 C30 C35 60.4(6) . . . . ? O4 C29 C30 C31 -117.5(3) . . . . ? O4 C29 C30 C29B 73.2(16) . . . . ? O4 C29B C30 C35 93.0(4) . . . . ? O4 C29B C30 C31 -90.2(5) . . . . ? O4 C29B C30 C29 -76.9(17) . . . . ? C35 C30 C31 C32 0.5(3) . . . . ? C29 C30 C31 C32 178.7(4) . . . . ? C29B C30 C31 C32 -176.0(5) . . . . ? C30 C31 C32 C33 -0.6(3) . . . . ? C31 C32 C33 C34 0.4(3) . . . . ? C32 C33 C34 C35 -0.2(3) . . . . ? C31 C30 C35 C34 -0.3(3) . . . . ? C29 C30 C35 C34 -178.1(5) . . . . ? C29B C30 C35 C34 176.9(4) . . . . ? C33 C34 C35 C30 0.2(4) . . . . ? O1 C20 O2 C21 2.1(2) . . . . ? N1 C20 O2 C21 -177.44(12) . . . . ? C22 C21 O2 C20 -129.50(14) . . . . ? O3 C28 O4 C29B -15.4(4) . . . . ? N3 C28 O4 C29B 158.7(3) . . . . ? O3 C28 O4 C29 9.4(3) . . . . ? N3 C28 O4 C29 -176.5(3) . . . . ? C30 C29B O4 C28 167.5(3) . . . . ? C30 C29B O4 C29 68.1(17) . . . . ? C30 C29 O4 C28 -173.2(3) . . . . ? C30 C29 O4 C29B -82.7(19) . . . . ? O1 C20 N1 C18 2.1(2) . . . . ? O2 C20 N1 C18 -178.32(12) . . . . ? O1 C20 N1 C17 171.00(15) . . . . ? O2 C20 N1 C17 -9.45(19) . . . . ? N3 C18 N1 C20 -7.9(2) . . . . ? N2 C18 N1 C20 168.50(13) . . . . ? N3 C18 N1 C17 -177.83(14) . . . . ? N2 C18 N1 C17 -1.42(16) . . . . ? C16 C17 N1 C20 -167.17(13) . . . . ? C16 C17 N1 C18 3.06(15) . . . . ? N3 C18 N2 C19 -6.1(2) . . . . ? N1 C18 N2 C19 177.19(12) . . . . ? N3 C18 N2 C16 175.66(13) . . . . ? N1 C18 N2 C16 -1.03(16) . . . . ? C13 C19 N2 C18 -121.30(15) . . . . ? C13 C19 N2 C16 56.85(16) . . . . ? C15 C16 N2 C18 125.17(14) . . . . ? C17 C16 N2 C18 2.86(16) . . . . ? C15 C16 N2 C19 -53.19(17) . . . . ? C17 C16 N2 C19 -175.49(12) . . . . ? N2 C18 N3 C28 141.60(14) . . . . ? N1 C18 N3 C28 -42.5(2) . . . . ? O3 C28 N3 C18 -31.1(2) . . . . ? O4 C28 N3 C18 155.30(13) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.224 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.051 # Attachment 'streuff6.cif' data_streuff6 _database_code_depnum_ccdc_archive 'CCDC 677355' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H22 N3, C2 F3 O2' _chemical_formula_sum 'C14 H22 F3 N3 O2' _chemical_formula_weight 321.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 13.8901(9) _cell_length_b 5.9564(2) _cell_length_c 22.1517(11) _cell_angle_alpha 90.00 _cell_angle_beta 120.178(3) _cell_angle_gamma 90.00 _cell_volume 1584.33(14) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8754 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _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 9509 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_sigmaI/netI 0.0600 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 27.54 _reflns_number_total 3631 _reflns_number_gt 2148 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0984P)^2^+0.7127P] 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 3631 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1240 _refine_ls_R_factor_gt 0.0710 _refine_ls_wR_factor_ref 0.2096 _refine_ls_wR_factor_gt 0.1798 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 0.4201(2) -0.2851(4) -0.16406(13) 0.0397(6) Uani 1 1 d . . . H1A H 0.4088 -0.1816 -0.2021 0.048 Uiso 1 1 calc R . . H1B H 0.4027 -0.2018 -0.1320 0.048 Uiso 1 1 calc R . . C2 C 0.5417(2) -0.3573(5) -0.12421(14) 0.0455(7) Uani 1 1 d . . . H2A H 0.5616 -0.4268 -0.1571 0.055 Uiso 1 1 calc R . . H2B H 0.5894 -0.2235 -0.1035 0.055 Uiso 1 1 calc R . . C3 C 0.5638(2) -0.5235(5) -0.06679(14) 0.0481(7) Uani 1 1 d . . . H3A H 0.5532 -0.4483 -0.0307 0.058 Uiso 1 1 calc R . . H3B H 0.6419 -0.5757 -0.0444 0.058 Uiso 1 1 calc R . . C4 C 0.4857(2) -0.7246(4) -0.09577(15) 0.0473(7) Uani 1 1 d . . . H4A H 0.5042 -0.8126 -0.1265 0.057 Uiso 1 1 calc R . . H4B H 0.4969 -0.8228 -0.0567 0.057 Uiso 1 1 calc R . . C5 C 0.3644(2) -0.6520(4) -0.13689(14) 0.0439(7) Uani 1 1 d . . . H5A H 0.3436 -0.5834 -0.1043 0.053 Uiso 1 1 calc R . . H5B H 0.3173 -0.7868 -0.1575 0.053 Uiso 1 1 calc R . . C6 C 0.3391(2) -0.4837(4) -0.19563(13) 0.0369(6) Uani 1 1 d . . . C7 C 0.3476(2) -0.5973(5) -0.25515(15) 0.0494(7) Uani 1 1 d . . . H7A H 0.4258 -0.6432 -0.2375 0.059 Uiso 1 1 calc R . . H7B H 0.3013 -0.7349 -0.2696 0.059 Uiso 1 1 calc R . . C8 C 0.3100(2) -0.4457(6) -0.31901(14) 0.0552(8) Uani 1 1 d . . . H8A H 0.3609 -0.3155 -0.3063 0.066 Uiso 1 1 calc R . . H8B H 0.3132 -0.5303 -0.3564 0.066 Uiso 1 1 calc R . . C9 C 0.1933(2) -0.3646(5) -0.34514(14) 0.0504(7) Uani 1 1 d . . . H9 H 0.1408 -0.4945 -0.3646 0.060 Uiso 1 1 calc R . . C10 C 0.1506(3) -0.1733(6) -0.39801(15) 0.0625(9) Uani 1 1 d . . . H10A H 0.2128 -0.0835 -0.3950 0.075 Uiso 1 1 calc R . . H10B H 0.1043 -0.2304 -0.4462 0.075 Uiso 1 1 calc R . . C11 C 0.1124(2) -0.0955(4) -0.31070(12) 0.0382(6) Uani 1 1 d . . . C12 C 0.2192(2) -0.4001(4) -0.22470(13) 0.0401(6) Uani 1 1 d . . . H12A H 0.1684 -0.5301 -0.2364 0.048 Uiso 1 1 calc R . . H12B H 0.2145 -0.3094 -0.1888 0.048 Uiso 1 1 calc R . . C13 C 0.1815(3) -0.9013(7) -0.05524(15) 0.0628(9) Uani 1 1 d . . . C14 C 0.0947(2) -1.0860(5) -0.09318(13) 0.0438(7) Uani 1 1 d . . . F1 F 0.16484(17) -0.7207(3) -0.09369(11) 0.0776(6) Uani 1 1 d . . . F2 F 0.28281(16) -0.9716(4) -0.03859(13) 0.1049(9) Uani 1 1 d . . . F3 F 0.1844(2) -0.8285(5) 0.00222(12) 0.1218(11) Uani 1 1 d . . . N1 N 0.0740(2) 0.0125(4) -0.27555(12) 0.0429(6) Uani 1 1 d . . . N2 N 0.0842(2) -0.0425(5) -0.37631(11) 0.0524(7) Uani 1 1 d . . . N3 N 0.18497(18) -0.2642(4) -0.28706(10) 0.0422(6) Uani 1 1 d . . . O1 O 0.07267(17) -1.1235(4) -0.15409(9) 0.0583(6) Uani 1 1 d . . . O2 O 0.05470(18) -1.1746(4) -0.06063(10) 0.0628(6) Uani 1 1 d . . . H1N H 0.088(3) -0.031(6) -0.2372(19) 0.075 Uiso 1 1 d . . . H2N H 0.027(3) 0.115(6) -0.2978(19) 0.075 Uiso 1 1 d . . . H3N H 0.045(3) 0.075(6) -0.3971(18) 0.075 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 0.0463(15) 0.0367(13) 0.0381(13) -0.0022(11) 0.0226(12) -0.0055(12) C2 0.0404(15) 0.0481(15) 0.0459(15) -0.0015(12) 0.0202(12) -0.0106(13) C3 0.0426(15) 0.0487(16) 0.0491(16) 0.0031(13) 0.0202(13) -0.0018(13) C4 0.0461(16) 0.0394(14) 0.0559(17) 0.0060(12) 0.0253(14) 0.0014(12) C5 0.0409(15) 0.0371(14) 0.0534(16) 0.0027(12) 0.0234(13) -0.0054(12) C6 0.0360(13) 0.0376(13) 0.0406(14) -0.0037(11) 0.0219(12) -0.0028(11) C7 0.0436(15) 0.0540(17) 0.0507(16) -0.0159(13) 0.0238(13) 0.0007(13) C8 0.0549(18) 0.075(2) 0.0415(15) -0.0131(14) 0.0285(14) 0.0093(15) C9 0.0474(16) 0.0679(19) 0.0384(15) -0.0114(13) 0.0235(13) 0.0067(14) C10 0.0602(19) 0.099(2) 0.0339(15) -0.0002(15) 0.0277(14) 0.0250(18) C11 0.0337(13) 0.0514(15) 0.0319(13) -0.0063(11) 0.0181(11) -0.0016(12) C12 0.0388(14) 0.0463(15) 0.0402(14) 0.0000(11) 0.0236(12) 0.0000(12) C13 0.0460(18) 0.099(3) 0.0368(16) 0.0003(17) 0.0162(14) -0.0164(18) C14 0.0385(14) 0.0606(17) 0.0286(13) 0.0025(12) 0.0141(11) -0.0041(13) F1 0.0725(13) 0.0686(12) 0.0925(15) 0.0003(11) 0.0419(12) -0.0143(10) F2 0.0396(12) 0.1100(18) 0.129(2) 0.0269(15) 0.0151(12) -0.0035(11) F3 0.142(2) 0.169(2) 0.0660(14) -0.0528(16) 0.0610(15) -0.092(2) N1 0.0487(14) 0.0529(14) 0.0341(12) 0.0052(10) 0.0258(11) 0.0122(11) N2 0.0538(15) 0.0766(17) 0.0302(12) 0.0024(11) 0.0237(11) 0.0180(13) N3 0.0438(12) 0.0559(14) 0.0330(11) -0.0013(10) 0.0237(10) 0.0094(11) O1 0.0681(14) 0.0785(14) 0.0366(11) -0.0075(10) 0.0326(10) -0.0230(11) O2 0.0714(15) 0.0875(16) 0.0373(11) -0.0039(10) 0.0332(11) -0.0269(12) _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 1.522(4) . ? C1 C6 1.537(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.517(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.524(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.521(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.537(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C12 1.536(3) . ? C6 C7 1.538(3) . ? C7 C8 1.532(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.502(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N3 1.475(3) . ? C9 C10 1.524(4) . ? C9 H9 1.0000 . ? C10 N2 1.460(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N1 1.312(3) . ? C11 N3 1.331(3) . ? C11 N2 1.339(3) . ? C12 N3 1.459(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 F1 1.318(4) . ? C13 F3 1.326(4) . ? C13 F2 1.331(4) . ? C13 C14 1.533(4) . ? C14 O2 1.228(3) . ? C14 O1 1.245(3) . ? N1 H1N 0.81(4) . ? N1 H2N 0.84(4) . ? N2 H3N 0.86(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 C2 C1 C6 113.0(2) . . ? C2 C1 H1A 109.0 . . ? C6 C1 H1A 109.0 . . ? C2 C1 H1B 109.0 . . ? C6 C1 H1B 109.0 . . ? H1A C1 H1B 107.8 . . ? C3 C2 C1 111.6(2) . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? C2 C3 C4 111.0(2) . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3B 109.4 . . ? C4 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C5 C4 C3 111.6(2) . . ? C5 C4 H4A 109.3 . . ? C3 C4 H4A 109.3 . . ? C5 C4 H4B 109.3 . . ? C3 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? C4 C5 C6 113.9(2) . . ? C4 C5 H5A 108.8 . . ? C6 C5 H5A 108.8 . . ? C4 C5 H5B 108.8 . . ? C6 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? C12 C6 C1 109.4(2) . . ? C12 C6 C5 107.7(2) . . ? C1 C6 C5 108.3(2) . . ? C12 C6 C7 108.5(2) . . ? C1 C6 C7 112.0(2) . . ? C5 C6 C7 110.8(2) . . ? C8 C7 C6 113.2(2) . . ? C8 C7 H7A 108.9 . . ? C6 C7 H7A 108.9 . . ? C8 C7 H7B 108.9 . . ? C6 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C9 C8 C7 110.3(2) . . ? C9 C8 H8A 109.6 . . ? C7 C8 H8A 109.6 . . ? C9 C8 H8B 109.6 . . ? C7 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? N3 C9 C8 109.7(2) . . ? N3 C9 C10 101.3(2) . . ? C8 C9 C10 117.7(3) . . ? N3 C9 H9 109.2 . . ? C8 C9 H9 109.2 . . ? C10 C9 H9 109.2 . . ? N2 C10 C9 102.3(2) . . ? N2 C10 H10A 111.3 . . ? C9 C10 H10A 111.3 . . ? N2 C10 H10B 111.3 . . ? C9 C10 H10B 111.3 . . ? H10A C10 H10B 109.2 . . ? N1 C11 N3 126.2(2) . . ? N1 C11 N2 123.0(3) . . ? N3 C11 N2 110.8(2) . . ? N3 C12 C6 110.2(2) . . ? N3 C12 H12A 109.6 . . ? C6 C12 H12A 109.6 . . ? N3 C12 H12B 109.6 . . ? C6 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? F1 C13 F3 105.3(3) . . ? F1 C13 F2 104.7(3) . . ? F3 C13 F2 108.6(3) . . ? F1 C13 C14 113.4(2) . . ? F3 C13 C14 113.4(3) . . ? F2 C13 C14 110.9(3) . . ? O2 C14 O1 128.4(3) . . ? O2 C14 C13 116.7(2) . . ? O1 C14 C13 114.8(2) . . ? C11 N1 H1N 120(3) . . ? C11 N1 H2N 115(2) . . ? H1N N1 H2N 124(4) . . ? C11 N2 C10 110.1(2) . . ? C11 N2 H3N 122(2) . . ? C10 N2 H3N 126(2) . . ? C11 N3 C12 127.8(2) . . ? C11 N3 C9 109.8(2) . . ? C12 N3 C9 118.0(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -56.5(3) . . . . ? C1 C2 C3 C4 54.7(3) . . . . ? C2 C3 C4 C5 -53.6(3) . . . . ? C3 C4 C5 C6 54.5(3) . . . . ? C2 C1 C6 C12 171.2(2) . . . . ? C2 C1 C6 C5 54.1(3) . . . . ? C2 C1 C6 C7 -68.4(3) . . . . ? C4 C5 C6 C12 -171.6(2) . . . . ? C4 C5 C6 C1 -53.4(3) . . . . ? C4 C5 C6 C7 69.8(3) . . . . ? C12 C6 C7 C8 55.1(3) . . . . ? C1 C6 C7 C8 -65.8(3) . . . . ? C5 C6 C7 C8 173.2(2) . . . . ? C6 C7 C8 C9 -56.1(3) . . . . ? C7 C8 C9 N3 52.0(3) . . . . ? C7 C8 C9 C10 167.1(2) . . . . ? N3 C9 C10 N2 -22.7(3) . . . . ? C8 C9 C10 N2 -142.2(3) . . . . ? C1 C6 C12 N3 70.5(3) . . . . ? C5 C6 C12 N3 -172.0(2) . . . . ? C7 C6 C12 N3 -52.0(3) . . . . ? F1 C13 C14 O2 -133.8(3) . . . . ? F3 C13 C14 O2 -13.7(4) . . . . ? F2 C13 C14 O2 108.8(3) . . . . ? F1 C13 C14 O1 45.0(4) . . . . ? F3 C13 C14 O1 165.1(3) . . . . ? F2 C13 C14 O1 -72.4(3) . . . . ? N1 C11 N2 C10 173.0(3) . . . . ? N3 C11 N2 C10 -5.4(3) . . . . ? C9 C10 N2 C11 18.3(3) . . . . ? N1 C11 N3 C12 15.0(4) . . . . ? N2 C11 N3 C12 -166.8(2) . . . . ? N1 C11 N3 C9 170.8(3) . . . . ? N2 C11 N3 C9 -11.0(3) . . . . ? C6 C12 N3 C11 -150.6(3) . . . . ? C6 C12 N3 C9 55.3(3) . . . . ? C8 C9 N3 C11 146.5(3) . . . . ? C10 C9 N3 C11 21.4(3) . . . . ? C8 C9 N3 C12 -55.0(3) . . . . ? C10 C9 N3 C12 179.9(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O1 0.81(4) 2.04(4) 2.819(3) 162(4) 1_565 N1 H2N O1 0.84(4) 2.00(4) 2.844(3) 175(3) 2_564 N2 H3N O2 0.86(4) 1.93(4) 2.787(3) 173(3) 2_564 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.858 _refine_diff_density_min -0.476 _refine_diff_density_rms 0.057