# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_FFA-TP _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 F3 N5 O4' _chemical_formula_weight 461.40 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9931(14) _cell_length_b 10.127(2) _cell_length_c 15.112(3) _cell_angle_alpha 95.46(3) _cell_angle_beta 96.70(3) _cell_angle_gamma 101.17(3) _cell_volume 1035.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 2738 _cell_measurement_theta_min 2.0651 _cell_measurement_theta_max 30.9148 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9480 _exptl_absorpt_correction_T_max 0.9606 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14435 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 28.28 _reflns_number_total 5008 _reflns_number_gt 4532 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1484P)^2^+0.2385P] 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 5008 _refine_ls_number_parameters 312 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0705 _refine_ls_R_factor_gt 0.0628 _refine_ls_wR_factor_ref 0.2320 _refine_ls_wR_factor_gt 0.2017 _refine_ls_goodness_of_fit_ref 1.188 _refine_ls_restrained_S_all 1.188 _refine_ls_shift/su_max 0.002 _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 O3 O 0.1419(2) 0.52772(13) 0.62301(9) 0.0304(3) Uani 1 1 d . . . O4 O 0.4577(2) 0.92547(15) 0.79198(9) 0.0366(3) Uani 1 1 d . . . N5 N 0.2973(2) 0.72782(15) 0.70628(10) 0.0256(3) Uani 1 1 d . . . N2 N 0.0760(2) 0.70202(16) 0.46998(10) 0.0267(3) Uani 1 1 d . . . N4 N 0.3475(2) 0.93844(15) 0.64631(10) 0.0269(3) Uani 1 1 d . . . N3 N 0.2020(2) 0.92489(16) 0.49031(10) 0.0290(3) Uani 1 1 d . . . C1 C 0.1714(2) 0.73316(17) 0.55690(11) 0.0243(4) Uani 1 1 d . . . C2 C 0.3725(2) 0.86837(18) 0.71946(12) 0.0267(4) Uani 1 1 d . . . C3 C 0.3297(3) 0.65326(19) 0.78359(12) 0.0293(4) Uani 1 1 d . . . H3A H 0.2097 0.5866 0.7871 0.044 Uiso 1 1 calc R . . H3B H 0.3628 0.7170 0.8388 0.044 Uiso 1 1 calc R . . H3C H 0.4382 0.6065 0.7765 0.044 Uiso 1 1 calc R . . C4 C 0.2452(2) 0.87040(17) 0.56700(11) 0.0251(4) Uani 1 1 d . . . C5 C 0.1968(2) 0.65160(17) 0.62677(12) 0.0246(4) Uani 1 1 d . . . C6 C 0.4204(3) 1.08465(19) 0.65745(14) 0.0346(4) Uani 1 1 d . . . H6A H 0.4750 1.1115 0.6035 0.052 Uiso 1 1 calc R . . H6B H 0.5233 1.1103 0.7095 0.052 Uiso 1 1 calc R . . H6C H 0.3120 1.1305 0.6669 0.052 Uiso 1 1 calc R . . C7 C 0.0988(3) 0.81830(19) 0.43371(12) 0.0300(4) Uani 1 1 d . . . H7 H 0.0470 0.8248 0.3737 0.036 Uiso 1 1 calc R . . O2 O 0.2842(2) 0.17140(14) 0.43897(9) 0.0306(3) Uani 1 1 d . . . O1 O 0.0958(2) 0.06499(13) 0.31310(9) 0.0316(3) Uani 1 1 d . . . N1 N 0.0598(2) 0.20581(16) 0.17374(10) 0.0285(3) Uani 1 1 d . . . C8 C 0.3352(3) 0.41792(18) 0.37923(12) 0.0274(4) Uani 1 1 d . . . H8 H 0.3825 0.4079 0.4393 0.033 Uiso 1 1 calc R . . C9 C 0.2327(2) 0.30303(17) 0.32155(11) 0.0245(4) Uani 1 1 d . . . C10 C 0.1971(2) 0.16940(18) 0.35579(11) 0.0252(4) Uani 1 1 d . . . F1 F 0.3350(3) 0.43077(17) -0.08837(11) 0.0688(5) Uani 1 1 d . . . C11 C 0.3694(3) 0.54525(18) 0.35117(13) 0.0302(4) Uani 1 1 d . . . H11 H 0.4429 0.6215 0.3906 0.036 Uiso 1 1 calc R . . C12 C 0.2939(3) 0.55955(19) 0.26378(13) 0.0304(4) Uani 1 1 d . . . H12 H 0.3125 0.6470 0.2443 0.037 Uiso 1 1 calc R . . C13 C 0.1929(3) 0.44866(19) 0.20531(12) 0.0283(4) Uani 1 1 d . . . H13 H 0.1428 0.4610 0.1462 0.034 Uiso 1 1 calc R . . C14 C 0.0175(3) 0.19583(18) 0.07978(12) 0.0280(4) Uani 1 1 d . . . F3 F 0.1787(3) 0.30482(18) -0.20634(9) 0.0706(6) Uani 1 1 d . . . C15 C 0.1031(3) 0.2389(2) -0.06658(13) 0.0375(5) Uani 1 1 d . . . C16 C 0.1506(3) 0.25844(19) 0.02678(12) 0.0311(4) Uani 1 1 d . . . H16 H 0.2727 0.3140 0.0541 0.037 Uiso 1 1 calc R . . C17 C 0.1624(2) 0.31748(17) 0.23158(11) 0.0250(4) Uani 1 1 d . . . C18 C -0.1607(3) 0.1134(2) 0.03882(14) 0.0353(4) Uani 1 1 d . . . H18 H -0.2522 0.0714 0.0746 0.042 Uiso 1 1 calc R . . F2 F 0.4007(3) 0.2373(2) -0.12400(14) 0.0823(7) Uani 1 1 d . . . C19 C -0.0746(4) 0.1555(2) -0.10717(14) 0.0437(5) Uani 1 1 d . . . H19 H -0.1062 0.1420 -0.1707 0.052 Uiso 1 1 calc R . . C20 C -0.2043(3) 0.0927(2) -0.05374(15) 0.0429(5) Uani 1 1 d . . . H20 H -0.3246 0.0349 -0.0810 0.051 Uiso 1 1 calc R . . C21 C 0.2526(5) 0.3031(3) -0.12084(15) 0.0496(6) Uani 1 1 d . . . H3 H 0.005(4) 0.616(3) 0.4387(18) 0.041(7) Uiso 1 1 d . . . H2 H 0.047(5) 0.137(4) 0.201(2) 0.068(10) Uiso 1 1 d . . . H1 H 0.267(5) 0.082(4) 0.457(2) 0.068(10) 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 O3 0.0349(7) 0.0225(6) 0.0307(7) -0.0006(5) -0.0006(5) 0.0029(5) O4 0.0403(7) 0.0340(7) 0.0280(7) -0.0059(5) -0.0027(6) -0.0019(6) N5 0.0271(7) 0.0243(7) 0.0234(7) -0.0013(6) 0.0008(5) 0.0039(5) N2 0.0302(7) 0.0260(7) 0.0217(7) -0.0033(5) 0.0011(5) 0.0046(6) N4 0.0293(7) 0.0235(7) 0.0249(7) -0.0026(5) 0.0036(5) 0.0007(5) N3 0.0342(8) 0.0270(7) 0.0252(7) 0.0006(6) 0.0065(6) 0.0043(6) C1 0.0257(7) 0.0222(8) 0.0223(8) -0.0027(6) 0.0015(6) 0.0019(6) C2 0.0255(7) 0.0257(8) 0.0267(8) -0.0025(6) 0.0027(6) 0.0030(6) C3 0.0308(8) 0.0300(8) 0.0262(8) 0.0023(7) -0.0007(6) 0.0075(7) C4 0.0264(7) 0.0240(8) 0.0240(8) -0.0013(6) 0.0055(6) 0.0038(6) C5 0.0239(7) 0.0246(8) 0.0240(8) -0.0022(6) 0.0021(6) 0.0052(6) C6 0.0411(10) 0.0239(9) 0.0328(9) -0.0042(7) 0.0044(8) -0.0036(7) C7 0.0357(9) 0.0280(9) 0.0252(8) -0.0004(7) 0.0054(7) 0.0049(7) O2 0.0371(7) 0.0270(7) 0.0250(7) 0.0026(5) 0.0004(5) 0.0028(5) O1 0.0399(7) 0.0251(6) 0.0251(6) -0.0006(5) 0.0034(5) -0.0022(5) N1 0.0336(8) 0.0250(7) 0.0230(7) -0.0007(6) 0.0016(6) -0.0003(6) C8 0.0280(8) 0.0270(8) 0.0252(8) -0.0004(7) 0.0031(6) 0.0031(6) C9 0.0252(7) 0.0237(8) 0.0233(8) -0.0010(6) 0.0052(6) 0.0023(6) C10 0.0252(7) 0.0261(8) 0.0234(8) -0.0002(6) 0.0056(6) 0.0031(6) F1 0.1076(15) 0.0521(9) 0.0407(8) 0.0068(7) 0.0235(9) -0.0065(9) C11 0.0308(8) 0.0247(8) 0.0308(9) -0.0033(7) 0.0027(7) -0.0007(6) C12 0.0339(9) 0.0245(8) 0.0328(9) 0.0026(7) 0.0066(7) 0.0050(7) C13 0.0302(8) 0.0280(8) 0.0267(8) 0.0030(7) 0.0038(6) 0.0065(6) C14 0.0320(8) 0.0267(8) 0.0234(8) -0.0021(6) -0.0005(6) 0.0064(7) F3 0.1222(17) 0.0659(11) 0.0246(7) 0.0111(7) 0.0128(8) 0.0175(10) C15 0.0588(13) 0.0331(10) 0.0248(9) 0.0032(7) 0.0041(8) 0.0209(9) C16 0.0395(9) 0.0289(9) 0.0245(8) 0.0011(7) 0.0024(7) 0.0086(7) C17 0.0234(7) 0.0260(8) 0.0243(8) -0.0015(6) 0.0039(6) 0.0038(6) C18 0.0355(9) 0.0329(9) 0.0341(10) -0.0061(8) -0.0012(7) 0.0076(7) F2 0.1006(15) 0.0958(15) 0.0815(13) 0.0466(11) 0.0579(12) 0.0519(12) C19 0.0671(14) 0.0409(11) 0.0233(9) -0.0045(8) -0.0064(9) 0.0233(10) C20 0.0423(11) 0.0445(12) 0.0360(11) -0.0110(9) -0.0111(8) 0.0123(9) C21 0.0829(18) 0.0435(12) 0.0275(10) 0.0073(9) 0.0136(10) 0.0211(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 O3 C5 1.233(2) . ? O4 C2 1.218(2) . ? N5 C5 1.396(2) . ? N5 C2 1.405(2) . ? N5 C3 1.469(2) . ? N2 C7 1.335(3) . ? N2 C1 1.380(2) . ? N2 H3 0.97(3) . ? N4 C4 1.369(2) . ? N4 C2 1.381(2) . ? N4 C6 1.456(2) . ? N3 C7 1.340(2) . ? N3 C4 1.358(2) . ? C1 C4 1.373(2) . ? C1 C5 1.417(3) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7 0.9500 . ? O2 C10 1.328(2) . ? O2 H1 0.96(4) . ? O1 C10 1.228(2) . ? N1 C17 1.382(2) . ? N1 C14 1.406(2) . ? N1 H2 0.84(4) . ? C8 C11 1.381(3) . ? C8 C9 1.402(2) . ? C8 H8 0.9500 . ? C9 C17 1.422(2) . ? C9 C10 1.481(2) . ? F1 C21 1.330(3) . ? C11 C12 1.395(3) . ? C11 H11 0.9500 . ? C12 C13 1.378(3) . ? C12 H12 0.9500 . ? C13 C17 1.406(3) . ? C13 H13 0.9500 . ? C14 C16 1.397(3) . ? C14 C18 1.397(3) . ? F3 C21 1.337(3) . ? C15 C19 1.397(3) . ? C15 C16 1.397(3) . ? C15 C21 1.492(3) . ? C16 H16 0.9500 . ? C18 C20 1.383(3) . ? C18 H18 0.9500 . ? F2 C21 1.339(3) . ? C19 C20 1.388(4) . ? C19 H19 0.9500 . ? C20 H20 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 C5 N5 C2 126.52(16) . . ? C5 N5 C3 116.71(15) . . ? C2 N5 C3 116.76(15) . . ? C7 N2 C1 106.29(15) . . ? C7 N2 H3 124.2(16) . . ? C1 N2 H3 129.5(16) . . ? C4 N4 C2 119.37(15) . . ? C4 N4 C6 121.72(16) . . ? C2 N4 C6 118.80(15) . . ? C7 N3 C4 103.54(15) . . ? C4 C1 N2 105.38(16) . . ? C4 C1 C5 122.83(16) . . ? N2 C1 C5 131.79(16) . . ? O4 C2 N4 121.59(17) . . ? O4 C2 N5 121.37(17) . . ? N4 C2 N5 117.04(15) . . ? N5 C3 H3A 109.5 . . ? N5 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N5 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N3 C4 N4 126.62(16) . . ? N3 C4 C1 111.41(16) . . ? N4 C4 C1 121.96(17) . . ? O3 C5 N5 120.45(17) . . ? O3 C5 C1 127.35(16) . . ? N5 C5 C1 112.20(15) . . ? N4 C6 H6A 109.5 . . ? N4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 N3 113.37(17) . . ? N2 C7 H7 123.3 . . ? N3 C7 H7 123.3 . . ? C10 O2 H1 111(2) . . ? C17 N1 C14 127.35(16) . . ? C17 N1 H2 110(2) . . ? C14 N1 H2 121(2) . . ? C11 C8 C9 121.79(17) . . ? C11 C8 H8 119.1 . . ? C9 C8 H8 119.1 . . ? C8 C9 C17 119.28(16) . . ? C8 C9 C10 119.44(16) . . ? C17 C9 C10 121.28(15) . . ? O1 C10 O2 121.77(17) . . ? O1 C10 C9 124.46(16) . . ? O2 C10 C9 113.77(15) . . ? C8 C11 C12 118.65(17) . . ? C8 C11 H11 120.7 . . ? C12 C11 H11 120.7 . . ? C13 C12 C11 120.99(18) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C17 121.22(17) . . ? C12 C13 H13 119.4 . . ? C17 C13 H13 119.4 . . ? C16 C14 C18 119.65(17) . . ? C16 C14 N1 122.57(16) . . ? C18 C14 N1 117.68(17) . . ? C19 C15 C16 120.5(2) . . ? C19 C15 C21 121.5(2) . . ? C16 C15 C21 117.9(2) . . ? C15 C16 C14 119.61(19) . . ? C15 C16 H16 120.2 . . ? C14 C16 H16 120.2 . . ? N1 C17 C13 121.67(16) . . ? N1 C17 C9 120.27(16) . . ? C13 C17 C9 117.99(16) . . ? C20 C18 C14 120.2(2) . . ? C20 C18 H18 119.9 . . ? C14 C18 H18 119.9 . . ? C20 C19 C15 119.28(19) . . ? C20 C19 H19 120.4 . . ? C15 C19 H19 120.4 . . ? C18 C20 C19 120.8(2) . . ? C18 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? F1 C21 F3 106.6(2) . . ? F1 C21 F2 106.0(3) . . ? F3 C21 F2 105.7(2) . . ? F1 C21 C15 112.90(19) . . ? F3 C21 C15 113.1(2) . . ? F2 C21 C15 112.0(2) . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.435 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.083 _database_code_depnum_ccdc_archive 'CCDC 960220' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_FFA-2pyridone _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H15 F3 N2 O3' _chemical_formula_weight 376.33 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5628(15) _cell_length_b 7.6450(15) _cell_length_c 14.552(3) _cell_angle_alpha 90.45(3) _cell_angle_beta 92.14(3) _cell_angle_gamma 95.81(3) _cell_volume 836.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 2214 _cell_measurement_theta_min 2.6782 _cell_measurement_theta_max 30.8858 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9602 _exptl_absorpt_correction_T_max 0.9732 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12293 _diffrn_reflns_av_R_equivalents 0.0372 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4091 _reflns_number_gt 3348 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0915P)^2^+0.3318P] 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 4091 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0979 _refine_ls_R_factor_gt 0.0789 _refine_ls_wR_factor_ref 0.2023 _refine_ls_wR_factor_gt 0.1889 _refine_ls_goodness_of_fit_ref 1.184 _refine_ls_restrained_S_all 1.184 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.0508(2) 0.7449(2) 0.46428(12) 0.0296(4) Uani 1 1 d . . . F1 F 1.1017(2) 1.3609(2) 0.06521(12) 0.0468(5) Uani 1 1 d . . . O2 O 0.8110(2) 0.7528(3) 0.54941(12) 0.0324(4) Uani 1 1 d . . . N1 N 1.0365(3) 0.8704(3) 0.29386(14) 0.0258(4) Uani 1 1 d . . . F2 F 1.2071(3) 1.2485(2) -0.05375(10) 0.0469(5) Uani 1 1 d . . . F3 F 1.3828(2) 1.3477(2) 0.05681(13) 0.0493(5) Uani 1 1 d . . . C1 C 1.1298(3) 1.0618(3) 0.16702(16) 0.0241(5) Uani 1 1 d . . . H1 H 1.0856 1.1591 0.1963 0.029 Uiso 1 1 calc R . . C2 C 1.2774(3) 0.9423(3) 0.03864(16) 0.0268(5) Uani 1 1 d . . . H2A H 1.3279 0.9574 -0.0199 0.032 Uiso 1 1 calc R . . C3 C 0.6210(3) 0.9026(3) 0.41650(16) 0.0261(5) Uani 1 1 d . . . H3 H 0.5743 0.8765 0.4751 0.031 Uiso 1 1 calc R . . C4 C 0.8671(3) 0.9073(3) 0.31323(16) 0.0236(5) Uani 1 1 d . . . C5 C 0.7950(3) 0.8668(3) 0.39984(15) 0.0229(5) Uani 1 1 d . . . C6 C 1.2067(3) 1.0808(3) 0.08199(16) 0.0248(5) Uani 1 1 d . . . C7 C 1.2728(3) 0.7813(3) 0.08275(17) 0.0278(5) Uani 1 1 d . . . H7 H 1.3249 0.6867 0.0554 0.033 Uiso 1 1 calc R . . C8 C 1.1926(3) 0.7583(3) 0.16644(17) 0.0264(5) Uani 1 1 d . . . H8 H 1.1881 0.6470 0.1953 0.032 Uiso 1 1 calc R . . C9 C 0.8976(3) 0.7840(3) 0.47337(16) 0.0250(5) Uani 1 1 d . . . C10 C 1.1184(3) 0.8963(3) 0.20897(15) 0.0238(5) Uani 1 1 d . . . C11 C 0.5859(3) 1.0127(3) 0.26471(16) 0.0261(5) Uani 1 1 d . . . H11 H 0.5149 1.0618 0.2184 0.031 Uiso 1 1 calc R . . C12 C 0.5153(3) 0.9744(3) 0.35069(16) 0.0267(5) Uani 1 1 d . . . H12 H 0.3975 0.9973 0.3633 0.032 Uiso 1 1 calc R . . C13 C 0.7566(3) 0.9803(3) 0.24650(16) 0.0251(5) Uani 1 1 d . . . H13 H 0.8013 1.0075 0.1876 0.030 Uiso 1 1 calc R . . C14 C 1.2224(3) 1.2581(3) 0.03799(17) 0.0296(5) Uani 1 1 d . . . O3 O 1.0334(2) 0.3873(2) 0.31617(11) 0.0289(4) Uani 1 1 d . . . N2 N 0.7665(3) 0.3862(3) 0.38473(14) 0.0257(4) Uani 1 1 d . . . C15 C 0.5911(3) 0.4122(3) 0.38428(17) 0.0290(5) Uani 1 1 d . . . H15 H 0.5248 0.3849 0.4374 0.035 Uiso 1 1 calc R . . C16 C 0.6124(4) 0.5154(3) 0.23161(18) 0.0315(6) Uani 1 1 d . . . H16 H 0.5593 0.5637 0.1787 0.038 Uiso 1 1 calc R . . C17 C 0.7862(3) 0.4848(3) 0.23159(16) 0.0291(5) Uani 1 1 d . . . H17 H 0.8518 0.5084 0.1779 0.035 Uiso 1 1 calc R . . C18 C 0.8721(3) 0.4178(3) 0.31100(16) 0.0249(5) Uani 1 1 d . . . C19 C 0.5097(3) 0.4765(3) 0.30904(19) 0.0318(6) Uani 1 1 d . . . H19 H 0.3872 0.4946 0.3085 0.038 Uiso 1 1 calc R . . H4 H 0.823(4) 0.337(4) 0.435(2) 0.044(9) Uiso 1 1 d . . . H2 H 0.874(6) 0.692(6) 0.591(3) 0.082(13) Uiso 1 1 d . . . H5 H 1.089(4) 0.796(4) 0.333(2) 0.050(9) 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 O1 0.0255(9) 0.0397(10) 0.0249(9) 0.0056(7) 0.0029(7) 0.0079(7) F1 0.0575(11) 0.0337(9) 0.0530(11) 0.0123(7) 0.0187(9) 0.0167(8) O2 0.0286(10) 0.0464(11) 0.0241(9) 0.0091(8) 0.0062(7) 0.0107(8) N1 0.0242(11) 0.0326(11) 0.0216(10) 0.0056(8) 0.0018(8) 0.0066(8) F2 0.0800(14) 0.0360(9) 0.0246(8) 0.0064(6) -0.0009(8) 0.0056(8) F3 0.0426(10) 0.0356(9) 0.0660(12) 0.0120(8) -0.0090(8) -0.0108(7) C1 0.0217(11) 0.0268(11) 0.0242(11) -0.0001(8) 0.0013(9) 0.0045(9) C2 0.0252(12) 0.0318(12) 0.0233(11) 0.0016(9) 0.0026(9) 0.0025(9) C3 0.0278(13) 0.0270(11) 0.0236(11) -0.0001(9) 0.0042(9) 0.0024(9) C4 0.0223(12) 0.0235(11) 0.0244(11) -0.0014(8) -0.0001(9) 0.0006(9) C5 0.0223(12) 0.0240(11) 0.0220(11) -0.0012(8) -0.0002(9) 0.0012(9) C6 0.0222(12) 0.0283(12) 0.0235(11) 0.0004(9) -0.0003(9) 0.0006(9) C7 0.0266(13) 0.0284(12) 0.0290(12) 0.0000(9) 0.0044(10) 0.0048(10) C8 0.0240(12) 0.0269(12) 0.0288(12) 0.0029(9) 0.0022(9) 0.0037(9) C9 0.0256(12) 0.0247(11) 0.0240(11) -0.0012(8) 0.0005(9) -0.0007(9) C10 0.0189(11) 0.0303(12) 0.0218(11) 0.0025(9) -0.0001(9) 0.0005(9) C11 0.0264(13) 0.0277(12) 0.0240(11) 0.0003(9) -0.0039(9) 0.0044(9) C12 0.0223(12) 0.0295(12) 0.0287(12) -0.0016(9) -0.0001(9) 0.0044(9) C13 0.0251(12) 0.0278(12) 0.0223(11) 0.0007(8) 0.0004(9) 0.0021(9) C14 0.0299(13) 0.0315(13) 0.0277(12) 0.0013(9) 0.0028(10) 0.0040(10) O3 0.0251(9) 0.0355(9) 0.0269(9) 0.0044(7) 0.0028(7) 0.0061(7) N2 0.0243(11) 0.0286(10) 0.0247(10) 0.0029(8) 0.0010(8) 0.0047(8) C15 0.0266(13) 0.0289(12) 0.0316(13) 0.0022(9) 0.0036(10) 0.0023(10) C16 0.0351(14) 0.0280(12) 0.0307(13) 0.0045(9) -0.0062(10) 0.0020(10) C17 0.0327(14) 0.0306(12) 0.0241(12) 0.0037(9) 0.0003(10) 0.0031(10) C18 0.0273(13) 0.0216(11) 0.0257(11) 0.0002(8) 0.0017(9) 0.0013(9) C19 0.0255(13) 0.0311(13) 0.0389(14) 0.0049(10) -0.0008(11) 0.0037(10) _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 O1 C9 1.236(3) . ? F1 C14 1.333(3) . ? O2 C9 1.318(3) . ? O2 H2 0.92(5) . ? N1 C4 1.378(3) . ? N1 C10 1.409(3) . ? N1 H5 0.91(4) . ? F2 C14 1.337(3) . ? F3 C14 1.350(3) . ? C1 C6 1.389(3) . ? C1 C10 1.405(3) . ? C1 H1 0.9500 . ? C2 C7 1.390(3) . ? C2 C6 1.391(3) . ? C2 H2A 0.9500 . ? C3 C12 1.377(3) . ? C3 C5 1.401(3) . ? C3 H3 0.9500 . ? C4 C13 1.412(3) . ? C4 C5 1.416(3) . ? C5 C9 1.482(3) . ? C6 C14 1.499(3) . ? C7 C8 1.385(3) . ? C7 H7 0.9500 . ? C8 C10 1.396(3) . ? C8 H8 0.9500 . ? C11 C13 1.374(3) . ? C11 C12 1.400(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? O3 C18 1.265(3) . ? N2 C15 1.361(3) . ? N2 C18 1.370(3) . ? N2 H4 0.94(3) . ? C15 C19 1.356(4) . ? C15 H15 0.9500 . ? C16 C17 1.359(4) . ? C16 C19 1.409(4) . ? C16 H16 0.9500 . ? C17 C18 1.428(3) . ? C17 H17 0.9500 . ? C19 H19 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 C9 O2 H2 112(3) . . ? C4 N1 C10 126.0(2) . . ? C4 N1 H5 117(2) . . ? C10 N1 H5 115(2) . . ? C6 C1 C10 118.9(2) . . ? C6 C1 H1 120.6 . . ? C10 C1 H1 120.6 . . ? C7 C2 C6 118.7(2) . . ? C7 C2 H2A 120.7 . . ? C6 C2 H2A 120.7 . . ? C12 C3 C5 122.1(2) . . ? C12 C3 H3 118.9 . . ? C5 C3 H3 118.9 . . ? N1 C4 C13 121.4(2) . . ? N1 C4 C5 121.0(2) . . ? C13 C4 C5 117.5(2) . . ? C3 C5 C4 119.5(2) . . ? C3 C5 C9 118.7(2) . . ? C4 C5 C9 121.8(2) . . ? C1 C6 C2 121.9(2) . . ? C1 C6 C14 119.0(2) . . ? C2 C6 C14 119.0(2) . . ? C8 C7 C2 120.3(2) . . ? C8 C7 H7 119.8 . . ? C2 C7 H7 119.8 . . ? C7 C8 C10 120.9(2) . . ? C7 C8 H8 119.5 . . ? C10 C8 H8 119.5 . . ? O1 C9 O2 122.5(2) . . ? O1 C9 C5 123.2(2) . . ? O2 C9 C5 114.3(2) . . ? C8 C10 C1 119.2(2) . . ? C8 C10 N1 120.2(2) . . ? C1 C10 N1 120.6(2) . . ? C13 C11 C12 120.9(2) . . ? C13 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C3 C12 C11 118.4(2) . . ? C3 C12 H12 120.8 . . ? C11 C12 H12 120.8 . . ? C11 C13 C4 121.6(2) . . ? C11 C13 H13 119.2 . . ? C4 C13 H13 119.2 . . ? F1 C14 F2 106.8(2) . . ? F1 C14 F3 106.4(2) . . ? F2 C14 F3 105.1(2) . . ? F1 C14 C6 113.5(2) . . ? F2 C14 C6 112.8(2) . . ? F3 C14 C6 111.8(2) . . ? C15 N2 C18 123.9(2) . . ? C15 N2 H4 122.0(19) . . ? C18 N2 H4 113.9(19) . . ? C19 C15 N2 120.9(2) . . ? C19 C15 H15 119.6 . . ? N2 C15 H15 119.6 . . ? C17 C16 C19 120.9(2) . . ? C17 C16 H16 119.5 . . ? C19 C16 H16 119.5 . . ? C16 C17 C18 121.1(2) . . ? C16 C17 H17 119.5 . . ? C18 C17 H17 119.5 . . ? O3 C18 N2 120.2(2) . . ? O3 C18 C17 124.6(2) . . ? N2 C18 C17 115.2(2) . . ? C15 C19 C16 117.9(2) . . ? C15 C19 H19 121.0 . . ? C16 C19 H19 121.0 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.362 _refine_diff_density_min -0.375 _refine_diff_density_rms 0.071 _database_code_depnum_ccdc_archive 'CCDC 960221' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_FFA-BP _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H28 F6 N4 O4' _chemical_formula_weight 718.64 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' 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.827(2) _cell_length_b 10.361(2) _cell_length_c 25.005(5) _cell_angle_alpha 84.67(3) _cell_angle_beta 81.34(3) _cell_angle_gamma 71.46(3) _cell_volume 2383.5(8) _cell_formula_units_Z 3 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 6225 _cell_measurement_theta_min 2.1964 _cell_measurement_theta_max 31.0138 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1110 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9855 _exptl_absorpt_correction_T_max 0.9939 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34188 _diffrn_reflns_av_R_equivalents 0.0648 _diffrn_reflns_av_sigmaI/netI 0.0674 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 28.28 _reflns_number_total 11714 _reflns_number_gt 8343 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11714 _refine_ls_number_parameters 724 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.2316 _refine_ls_R_factor_gt 0.1985 _refine_ls_wR_factor_ref 0.4988 _refine_ls_wR_factor_gt 0.4730 _refine_ls_goodness_of_fit_ref 1.572 _refine_ls_restrained_S_all 1.572 _refine_ls_shift/su_max 0.058 _refine_ls_shift/su_mean 0.012 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 O1 O -0.0843(4) 0.9187(4) 0.18072(15) 0.0492(9) Uani 1 1 d . . . O5 O 0.4227(4) 0.7440(4) 0.82286(16) 0.0512(10) Uani 1 1 d . . . O6 O 0.3340(4) 0.6153(4) 0.88637(15) 0.0450(9) Uani 1 1 d D . . O4 O 0.6595(4) 0.2916(4) 0.88060(16) 0.0459(9) Uani 1 1 d D . . H4 H 0.7342 0.2853 0.8945 0.069 Uiso 1 1 calc RD . . O2 O 0.0023(4) 1.0452(4) 0.11598(16) 0.0464(9) Uani 1 1 d D . . O3 O 0.7517(4) 0.4207(4) 0.81795(16) 0.0468(9) Uani 1 1 d . . . C1 C 0.2232(5) 0.6770(5) 0.8058(2) 0.0413(11) Uani 1 1 d . . . N3 N 0.3026(5) 0.8116(5) 0.73220(19) 0.0490(11) Uani 1 1 d D . . N2 N 0.6337(5) 0.4872(5) 0.72575(19) 0.0480(11) Uani 1 1 d D . . C2 C 0.1171(5) 0.9899(5) 0.19483(18) 0.0339(10) Uani 1 1 d . . . N1 N 0.0456(5) 0.8515(5) 0.27132(18) 0.0444(10) Uani 1 1 d D . . C3 C 0.0018(5) 0.9797(5) 0.1647(2) 0.0422(11) Uani 1 1 d . . . C4 C 0.3346(5) 0.6842(5) 0.8384(2) 0.0403(11) Uani 1 1 d . . . C5 C 0.1285(5) 0.6033(5) 0.8278(2) 0.0407(11) Uani 1 1 d . . . H5 H 0.1381 0.5593 0.8627 0.049 Uiso 1 1 calc R . . C6 C 0.4575(5) 0.2762(5) 0.8206(2) 0.0417(11) Uani 1 1 d . . . H6A H 0.4676 0.2307 0.8552 0.050 Uiso 1 1 calc R . . C7 C 0.2118(5) 0.7402(5) 0.75398(19) 0.0344(10) Uani 1 1 d . . . C8 C 0.5519(5) 0.3500(5) 0.8004(2) 0.0411(11) Uani 1 1 d . . . C9 C 0.1353(5) 0.9256(5) 0.2464(2) 0.0415(11) Uani 1 1 d . . . C10 C 0.0071(6) 0.6600(6) 0.7496(2) 0.0479(13) Uani 1 1 d . . . H10 H -0.0671 0.6551 0.7302 0.058 Uiso 1 1 calc R . . C11 C 0.2086(5) 1.0653(5) 0.1717(2) 0.0397(11) Uani 1 1 d . . . H11 H 0.1954 1.1087 0.1368 0.048 Uiso 1 1 calc R . . C12 C 0.2498(6) 0.9356(5) 0.2721(2) 0.0445(12) Uani 1 1 d . . . H12 H 0.2663 0.8900 0.3064 0.053 Uiso 1 1 calc R . . C13 C 0.4301(6) 0.4059(5) 0.7201(2) 0.0431(11) Uani 1 1 d . . . H13 H 0.4182 0.4508 0.6855 0.052 Uiso 1 1 calc R . . C14 C 0.3362(6) 1.0092(5) 0.2485(2) 0.0441(12) Uani 1 1 d . . . H14 H 0.4122 1.0139 0.2669 0.053 Uiso 1 1 calc R . . C15 C 0.3160(5) 0.8693(6) 0.6783(2) 0.0447(12) Uani 1 1 d . . . C16 C 0.7215(5) 0.7034(5) 0.6089(2) 0.0437(12) Uani 1 1 d . . . C17 C 0.6517(6) 0.4636(6) 0.6269(2) 0.0479(13) Uani 1 1 d . . . H17 H 0.6324 0.3788 0.6327 0.058 Uiso 1 1 calc R . . C18 C -0.0223(5) 0.6936(5) 0.3376(2) 0.0404(11) Uani 1 1 d . . . H18 H -0.0305 0.6426 0.3093 0.049 Uiso 1 1 calc R . . C19 C 0.6647(5) 0.3572(5) 0.8320(2) 0.0428(11) Uani 1 1 d . . . C20 C 0.6567(5) 0.5358(5) 0.6717(2) 0.0412(11) Uani 1 1 d . . . C21 C 0.5412(6) 0.4151(5) 0.7477(2) 0.0430(11) Uani 1 1 d . . . C22 C 0.3181(5) 1.0789(6) 0.1978(2) 0.0461(12) Uani 1 1 d . . . H22 H 0.3777 1.1326 0.1822 0.055 Uiso 1 1 calc R . . C23 C 0.6930(5) 0.6546(5) 0.6617(2) 0.0441(12) Uani 1 1 d . . . H23 H 0.6987 0.7035 0.6912 0.053 Uiso 1 1 calc R . . C24 C 0.0363(5) 0.8813(5) 0.3688(2) 0.0434(12) Uani 1 1 d . . . H24 H 0.0654 0.9609 0.3614 0.052 Uiso 1 1 calc R . . C25 C 0.0966(6) 0.7332(6) 0.7269(2) 0.0469(12) Uani 1 1 d . . . H25 H 0.0820 0.7800 0.6928 0.056 Uiso 1 1 calc R . . C26 C 0.0210(6) 0.5934(6) 0.7995(2) 0.0478(13) Uani 1 1 d . . . H26 H -0.0413 0.5418 0.8144 0.057 Uiso 1 1 calc R . . C27 C 0.0223(6) 0.8089(6) 0.3254(2) 0.0431(12) Uani 1 1 d . . . C28 C 0.3376(6) 0.8647(6) 0.5807(2) 0.0515(14) Uani 1 1 d . . . C29 C 0.3401(6) 0.9970(6) 0.6714(3) 0.0498(13) Uani 1 1 d . . . H29 H 0.3404 1.0432 0.7025 0.060 Uiso 1 1 calc R . . C30 C 0.3386(5) 0.3334(5) 0.7422(2) 0.0430(12) Uani 1 1 d . . . H30 H 0.2651 0.3292 0.7224 0.052 Uiso 1 1 calc R . . C31 C 0.3503(6) 0.2655(6) 0.7932(2) 0.0499(13) Uani 1 1 d . . . H31 H 0.2874 0.2145 0.8082 0.060 Uiso 1 1 calc R . . C32 C -0.0549(6) 0.6531(5) 0.3912(2) 0.0438(12) Uani 1 1 d . . . C33 C 0.6747(7) 0.5163(6) 0.5755(3) 0.0556(15) Uani 1 1 d . . . H33 H 0.6641 0.4704 0.5460 0.067 Uiso 1 1 calc R . . C34 C 0.3637(6) 1.0572(6) 0.6201(3) 0.0502(13) Uani 1 1 d . . . H34 H 0.3824 1.1423 0.6161 0.060 Uiso 1 1 calc R . . C35 C 0.3161(6) 0.8040(5) 0.6325(2) 0.0434(12) Uani 1 1 d . . . H35 H 0.3014 0.7171 0.6361 0.052 Uiso 1 1 calc R . . C36 C -0.0342(6) 0.7218(6) 0.4332(2) 0.0471(12) Uani 1 1 d . . . H36 H -0.0493 0.6889 0.4697 0.056 Uiso 1 1 calc R . . C37 C 0.7124(5) 0.6328(6) 0.5653(2) 0.0459(12) Uani 1 1 d . . . H37 H 0.7322 0.6655 0.5291 0.055 Uiso 1 1 calc R . . C38 C 0.0074(6) 0.8355(6) 0.4220(2) 0.0519(14) Uani 1 1 d . . . H38 H 0.0168 0.8843 0.4509 0.062 Uiso 1 1 calc R . . F2 F -0.0781(4) 0.4644(4) 0.44859(15) 0.0653(10) Uani 1 1 d . . . F3 F 0.7795(8) 0.8731(5) 0.54839(19) 0.123(2) Uani 1 1 d . . . F1 F -0.0968(5) 0.4592(4) 0.36501(16) 0.0811(13) Uani 1 1 d . . . C39 C -0.1213(7) 0.5416(6) 0.4051(3) 0.0523(13) Uani 1 1 d . . . C40 C 0.3593(6) 0.9911(6) 0.5751(3) 0.0524(14) Uani 1 1 d . . . H40 H 0.3714 1.0328 0.5400 0.063 Uiso 1 1 calc R . . F4 F 0.6855(4) 0.9339(4) 0.62670(19) 0.0779(12) Uani 1 1 d . . . C41 C 0.3289(7) 0.7957(7) 0.5335(2) 0.0593(15) Uani 1 1 d . . . F5 F 0.4262(5) 0.8075(5) 0.49187(17) 0.0937(14) Uani 1 1 d . . . F6 F 0.3498(5) 0.6616(4) 0.54186(16) 0.0783(12) Uani 1 1 d . . . C42 C 0.7706(7) 0.8289(6) 0.5991(2) 0.0539(14) Uani 1 1 d . . . N4 N 0.4580(4) 0.3586(4) 1.05851(18) 0.0394(9) Uani 1 1 d . . . N5 N -0.1316(5) 0.3104(4) 0.93650(18) 0.0423(10) Uani 1 1 d . . . C43 C -0.0269(5) 0.3185(5) 1.0160(2) 0.0387(11) Uani 1 1 d . . . H43 H -0.0369 0.3167 1.0544 0.046 Uiso 1 1 calc R . . C44 C 0.2178(5) 0.3400(5) 1.0658(2) 0.0387(11) Uani 1 1 d . . . H44 H 0.1323 0.3362 1.0884 0.046 Uiso 1 1 calc R . . C45 C 0.2255(5) 0.3372(5) 1.0107(2) 0.0380(10) Uani 1 1 d . . . C46 C 0.1070(5) 0.3251(5) 0.9295(2) 0.0393(11) Uani 1 1 d . . . H46 H 0.1906 0.3315 0.9062 0.047 Uiso 1 1 calc R . . C47 C 0.3524(5) 0.3470(5) 0.9796(2) 0.0386(10) Uani 1 1 d . . . H47 H 0.3615 0.3473 0.9413 0.046 Uiso 1 1 calc R . . C48 C -0.1389(5) 0.3122(5) 0.9904(2) 0.0419(11) Uani 1 1 d . . . H48 H -0.2261 0.3089 1.0120 0.050 Uiso 1 1 calc R . . C49 C 0.3368(5) 0.3486(5) 1.0886(2) 0.0416(11) Uani 1 1 d . . . H49 H 0.3309 0.3473 1.1269 0.050 Uiso 1 1 calc R . . C50 C 0.1031(5) 0.3278(4) 0.9853(2) 0.0349(10) Uani 1 1 d . . . C51 C 0.4654(5) 0.3562(5) 1.0047(2) 0.0388(10) Uani 1 1 d . . . H51 H 0.5516 0.3610 0.9828 0.047 Uiso 1 1 calc R . . C52 C -0.0087(5) 0.3134(5) 0.9077(2) 0.0393(11) Uani 1 1 d . . . H52 H 0.0006 0.3070 0.8696 0.047 Uiso 1 1 calc R . . N6 N 0.7955(4) 0.0228(5) 0.06202(19) 0.0448(10) Uani 1 1 d . . . C54 C 0.6892(5) 0.0167(5) -0.0180(2) 0.0406(11) Uani 1 1 d . . . H54 H 0.7000 0.0186 -0.0564 0.049 Uiso 1 1 calc R . . C53 C 0.5601(5) 0.0047(5) 0.01340(19) 0.0362(10) Uani 1 1 d . . . C55 C 0.7992(6) 0.0256(5) 0.0092(2) 0.0444(12) Uani 1 1 d . . . H55 H 0.8844 0.0344 -0.0123 0.053 Uiso 1 1 calc R . . C56 C 0.5568(6) -0.0003(5) 0.0694(2) 0.0426(11) Uani 1 1 d . . . H56 H 0.4754 -0.0125 0.0926 0.051 Uiso 1 1 calc R . . C57 C 0.6742(6) 0.0128(5) 0.0912(2) 0.0463(13) Uani 1 1 d . . . H57 H 0.6670 0.0146 0.1295 0.056 Uiso 1 1 calc R . . F7 F -0.2665(4) 0.5916(4) 0.41697(19) 0.0772(12) Uani 1 1 d . . . F8 F 0.2013(5) 0.8479(5) 0.51555(19) 0.1008(16) Uani 1 1 d . . . F9 F 0.9000(5) 0.8083(4) 0.6136(3) 0.119(2) Uani 1 1 d . . . H3A H 0.355(7) 0.841(7) 0.746(3) 0.09(2) Uiso 1 1 d D . . H2A H 0.671(9) 0.502(9) 0.751(3) 0.12(3) Uiso 1 1 d D . . H1A H -0.008(4) 0.837(4) 0.2527(16) 0.020(11) Uiso 1 1 d D . . H6 H 0.384(6) 0.646(6) 0.901(2) 0.060(19) Uiso 1 1 d D . . H2 H -0.035(10) 1.022(10) 0.093(3) 0.14(4) Uiso 1 1 d 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 O1 0.054(2) 0.065(2) 0.039(2) 0.0061(18) -0.0097(17) -0.0334(19) O5 0.053(2) 0.064(2) 0.045(2) 0.0037(19) -0.0086(17) -0.0296(19) O6 0.056(2) 0.049(2) 0.0381(19) 0.0079(16) -0.0127(17) -0.0274(17) O4 0.046(2) 0.046(2) 0.051(2) 0.0043(17) -0.0117(17) -0.0198(16) O2 0.046(2) 0.052(2) 0.038(2) -0.0009(17) -0.0005(16) -0.0133(16) O3 0.048(2) 0.059(2) 0.046(2) 0.0004(18) -0.0045(16) -0.0355(17) C1 0.044(3) 0.044(3) 0.043(3) -0.011(2) 0.000(2) -0.024(2) N3 0.055(3) 0.060(3) 0.042(3) -0.002(2) -0.012(2) -0.028(2) N2 0.054(3) 0.058(3) 0.035(2) 0.013(2) -0.003(2) -0.028(2) C2 0.039(2) 0.038(2) 0.026(2) 0.0027(19) 0.0026(18) -0.0181(19) N1 0.053(3) 0.052(3) 0.036(2) 0.0040(19) -0.0118(19) -0.025(2) C3 0.043(3) 0.044(3) 0.043(3) -0.002(2) -0.004(2) -0.019(2) C4 0.029(2) 0.052(3) 0.041(3) 0.001(2) -0.004(2) -0.017(2) C5 0.034(2) 0.049(3) 0.041(3) 0.000(2) -0.002(2) -0.018(2) C6 0.048(3) 0.050(3) 0.032(2) -0.003(2) -0.001(2) -0.022(2) C7 0.036(2) 0.035(2) 0.033(2) 0.0019(19) -0.0005(18) -0.0169(18) C8 0.036(2) 0.045(3) 0.044(3) -0.005(2) -0.007(2) -0.014(2) C9 0.034(2) 0.049(3) 0.047(3) -0.002(2) -0.004(2) -0.020(2) C10 0.037(3) 0.059(3) 0.046(3) -0.005(3) -0.004(2) -0.013(2) C11 0.042(3) 0.038(2) 0.038(3) -0.003(2) 0.006(2) -0.016(2) C12 0.051(3) 0.043(3) 0.038(3) 0.002(2) -0.013(2) -0.010(2) C13 0.048(3) 0.053(3) 0.034(3) 0.001(2) -0.007(2) -0.023(2) C14 0.041(3) 0.046(3) 0.047(3) -0.009(2) -0.006(2) -0.014(2) C15 0.037(3) 0.057(3) 0.040(3) 0.006(2) 0.000(2) -0.020(2) C16 0.036(2) 0.050(3) 0.040(3) 0.003(2) 0.004(2) -0.012(2) C17 0.044(3) 0.054(3) 0.049(3) 0.000(3) -0.013(2) -0.018(2) C18 0.035(2) 0.056(3) 0.032(2) 0.004(2) 0.0009(19) -0.020(2) C19 0.037(2) 0.047(3) 0.040(3) 0.000(2) -0.006(2) -0.007(2) C20 0.042(3) 0.043(3) 0.043(3) 0.004(2) -0.006(2) -0.020(2) C21 0.048(3) 0.041(3) 0.036(3) 0.002(2) -0.005(2) -0.009(2) C22 0.039(3) 0.053(3) 0.049(3) -0.006(2) 0.007(2) -0.023(2) C23 0.040(3) 0.046(3) 0.049(3) 0.001(2) -0.008(2) -0.018(2) C24 0.041(3) 0.037(2) 0.056(3) -0.004(2) -0.011(2) -0.014(2) C25 0.044(3) 0.052(3) 0.047(3) -0.011(2) -0.012(2) -0.012(2) C26 0.050(3) 0.049(3) 0.052(3) -0.012(3) -0.005(2) -0.024(2) C27 0.042(3) 0.052(3) 0.037(3) 0.001(2) -0.014(2) -0.013(2) C28 0.038(3) 0.065(4) 0.046(3) 0.008(3) -0.004(2) -0.013(2) C29 0.050(3) 0.047(3) 0.058(3) 0.001(3) -0.014(3) -0.020(2) C30 0.032(2) 0.049(3) 0.049(3) 0.000(2) -0.008(2) -0.013(2) C31 0.040(3) 0.060(3) 0.049(3) -0.006(3) -0.003(2) -0.014(2) C32 0.046(3) 0.045(3) 0.043(3) 0.002(2) -0.012(2) -0.017(2) C33 0.065(4) 0.057(3) 0.059(4) -0.013(3) -0.015(3) -0.032(3) C34 0.045(3) 0.050(3) 0.063(4) 0.009(3) -0.007(3) -0.027(2) C35 0.050(3) 0.045(3) 0.037(3) -0.005(2) -0.008(2) -0.015(2) C36 0.048(3) 0.053(3) 0.040(3) 0.007(2) -0.003(2) -0.018(2) C37 0.040(3) 0.061(3) 0.034(3) -0.003(2) -0.002(2) -0.012(2) C38 0.051(3) 0.062(3) 0.037(3) -0.005(3) -0.003(2) -0.009(3) F2 0.088(3) 0.060(2) 0.054(2) 0.0187(17) -0.0157(19) -0.0344(18) F3 0.248(7) 0.104(4) 0.052(3) -0.006(2) 0.005(3) -0.112(4) F1 0.133(4) 0.069(2) 0.059(2) -0.015(2) 0.009(2) -0.061(2) C39 0.060(3) 0.046(3) 0.054(3) 0.003(3) 0.000(3) -0.027(3) C40 0.038(3) 0.058(3) 0.060(4) 0.015(3) -0.012(2) -0.014(2) F4 0.074(3) 0.063(2) 0.101(3) -0.026(2) 0.010(2) -0.0313(19) C41 0.072(4) 0.060(4) 0.042(3) 0.006(3) -0.007(3) -0.019(3) F5 0.124(4) 0.118(4) 0.056(2) -0.009(2) 0.008(2) -0.069(3) F6 0.108(3) 0.074(2) 0.063(2) -0.003(2) -0.013(2) -0.043(2) C42 0.065(4) 0.061(4) 0.038(3) 0.007(3) -0.011(3) -0.025(3) N4 0.041(2) 0.035(2) 0.045(2) -0.0023(18) -0.0087(18) -0.0139(16) N5 0.051(2) 0.036(2) 0.040(2) 0.0115(18) -0.0109(19) -0.0143(17) C43 0.038(2) 0.044(3) 0.037(3) -0.003(2) -0.005(2) -0.017(2) C44 0.036(2) 0.043(3) 0.038(3) 0.004(2) -0.002(2) -0.0161(19) C45 0.045(3) 0.037(2) 0.034(2) 0.002(2) -0.004(2) -0.017(2) C46 0.038(2) 0.039(2) 0.042(3) -0.002(2) -0.008(2) -0.0123(19) C47 0.041(2) 0.034(2) 0.044(3) 0.001(2) -0.002(2) -0.0185(19) C48 0.038(3) 0.039(2) 0.042(3) 0.005(2) 0.000(2) -0.0070(19) C49 0.043(3) 0.029(2) 0.047(3) -0.002(2) -0.001(2) -0.0063(19) C50 0.033(2) 0.032(2) 0.041(3) -0.006(2) -0.0033(19) -0.0103(17) C51 0.044(3) 0.039(2) 0.033(2) 0.003(2) -0.005(2) -0.015(2) C52 0.036(2) 0.046(3) 0.035(3) -0.001(2) 0.0031(19) -0.014(2) N6 0.032(2) 0.056(3) 0.044(2) 0.001(2) -0.0040(18) -0.0118(18) C54 0.047(3) 0.033(2) 0.043(3) 0.000(2) -0.008(2) -0.014(2) C53 0.035(2) 0.036(2) 0.034(2) 0.002(2) 0.0016(19) -0.0093(18) C55 0.046(3) 0.037(2) 0.051(3) 0.001(2) -0.002(2) -0.017(2) C56 0.044(3) 0.043(3) 0.041(3) 0.004(2) -0.004(2) -0.016(2) C57 0.054(3) 0.047(3) 0.048(3) -0.001(2) -0.021(2) -0.024(2) F7 0.053(2) 0.065(2) 0.113(4) 0.013(2) 0.000(2) -0.0271(17) F8 0.094(3) 0.123(4) 0.091(3) -0.023(3) -0.051(3) -0.018(3) F9 0.067(3) 0.075(3) 0.228(7) 0.023(3) -0.050(3) -0.036(2) _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 O1 C3 1.212(6) . ? O5 C4 1.217(6) . ? O6 C4 1.338(6) . ? O6 H6 0.82(2) . ? O4 C19 1.338(6) . ? O4 H4 0.8400 . ? O2 C3 1.338(6) . ? O2 H2 0.81(2) . ? O3 C19 1.229(6) . ? C1 C7 1.400(7) . ? C1 C5 1.404(7) . ? C1 C4 1.483(6) . ? N3 C7 1.355(6) . ? N3 C15 1.428(7) . ? N3 H3A 0.82(2) . ? N2 C21 1.375(7) . ? N2 C20 1.409(7) . ? N2 H2A 0.83(2) . ? C2 C11 1.400(6) . ? C2 C9 1.405(7) . ? C2 C3 1.487(6) . ? N1 C9 1.389(6) . ? N1 C27 1.392(7) . ? N1 H1A 0.807(19) . ? C5 C26 1.391(7) . ? C5 H5 0.9500 . ? C6 C31 1.377(7) . ? C6 C8 1.392(7) . ? C6 H6A 0.9500 . ? C7 C25 1.427(6) . ? C8 C21 1.425(7) . ? C8 C19 1.479(6) . ? C9 C12 1.411(6) . ? C10 C25 1.365(8) . ? C10 C26 1.374(8) . ? C10 H10 0.9500 . ? C11 C22 1.389(7) . ? C11 H11 0.9500 . ? C12 C14 1.352(8) . ? C12 H12 0.9500 . ? C13 C30 1.370(7) . ? C13 C21 1.409(7) . ? C13 H13 0.9500 . ? C14 C22 1.405(8) . ? C14 H14 0.9500 . ? C15 C35 1.384(7) . ? C15 C29 1.407(7) . ? C16 C23 1.389(7) . ? C16 C37 1.398(7) . ? C16 C42 1.513(8) . ? C17 C33 1.364(8) . ? C17 C20 1.418(7) . ? C17 H17 0.9500 . ? C18 C32 1.387(7) . ? C18 C27 1.392(7) . ? C18 H18 0.9500 . ? C20 C23 1.378(7) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C38 1.389(8) . ? C24 C27 1.422(7) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C28 C40 1.384(8) . ? C28 C35 1.402(7) . ? C28 C41 1.462(8) . ? C29 C34 1.394(8) . ? C29 H29 0.9500 . ? C30 C31 1.400(8) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? C32 C36 1.395(7) . ? C32 C39 1.490(7) . ? C33 C37 1.364(8) . ? C33 H33 0.9500 . ? C34 C40 1.383(8) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? C36 C38 1.358(8) . ? C36 H36 0.9500 . ? C37 H37 0.9500 . ? C38 H38 0.9500 . ? F2 C39 1.328(7) . ? F3 C42 1.306(7) . ? F1 C39 1.322(7) . ? C39 F7 1.350(7) . ? C40 H40 0.9500 . ? F4 C42 1.321(7) . ? C41 F8 1.326(7) . ? C41 F5 1.328(8) . ? C41 F6 1.339(7) . ? C42 F9 1.321(7) . ? N4 C51 1.338(6) . ? N4 C49 1.338(7) . ? N5 C52 1.318(7) . ? N5 C48 1.340(7) . ? C43 C48 1.375(6) . ? C43 C50 1.414(7) . ? C43 H43 0.9500 . ? C44 C45 1.370(7) . ? C44 C49 1.407(7) . ? C44 H44 0.9500 . ? C45 C47 1.393(7) . ? C45 C50 1.475(7) . ? C46 C52 1.375(6) . ? C46 C50 1.393(7) . ? C46 H46 0.9500 . ? C47 C51 1.388(6) . ? C47 H47 0.9500 . ? C48 H48 0.9500 . ? C49 H49 0.9500 . ? C51 H51 0.9500 . ? C52 H52 0.9500 . ? N6 C55 1.313(7) . ? N6 C57 1.329(7) . ? C54 C55 1.391(7) . ? C54 C53 1.423(7) . ? C54 H54 0.9500 . ? C53 C56 1.393(7) . ? C53 C53 1.475(9) 2_655 ? C55 H55 0.9500 . ? C56 C57 1.396(7) . ? C56 H56 0.9500 . ? C57 H57 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 C4 O6 H6 101(5) . . ? C19 O4 H4 109.5 . . ? C3 O2 H2 118(8) . . ? C7 C1 C5 119.9(4) . . ? C7 C1 C4 121.7(4) . . ? C5 C1 C4 118.5(5) . . ? C7 N3 C15 127.6(4) . . ? C7 N3 H3A 131(6) . . ? C15 N3 H3A 101(6) . . ? C21 N2 C20 128.3(5) . . ? C21 N2 H2A 106(7) . . ? C20 N2 H2A 125(7) . . ? C11 C2 C9 119.3(4) . . ? C11 C2 C3 119.6(4) . . ? C9 C2 C3 121.0(4) . . ? C9 N1 C27 129.9(4) . . ? C9 N1 H1A 116(3) . . ? C27 N1 H1A 114(3) . . ? O1 C3 O2 121.7(5) . . ? O1 C3 C2 125.6(5) . . ? O2 C3 C2 112.7(4) . . ? O5 C4 O6 121.8(4) . . ? O5 C4 C1 123.7(5) . . ? O6 C4 C1 114.4(4) . . ? C26 C5 C1 121.3(5) . . ? C26 C5 H5 119.3 . . ? C1 C5 H5 119.3 . . ? C31 C6 C8 123.7(5) . . ? C31 C6 H6A 118.1 . . ? C8 C6 H6A 118.1 . . ? N3 C7 C1 120.5(4) . . ? N3 C7 C25 121.9(5) . . ? C1 C7 C25 117.5(4) . . ? C6 C8 C21 118.8(5) . . ? C6 C8 C19 120.9(5) . . ? C21 C8 C19 120.3(5) . . ? N1 C9 C2 121.3(4) . . ? N1 C9 C12 120.5(5) . . ? C2 C9 C12 118.2(5) . . ? C25 C10 C26 121.9(5) . . ? C25 C10 H10 119.0 . . ? C26 C10 H10 119.0 . . ? C22 C11 C2 122.4(5) . . ? C22 C11 H11 118.8 . . ? C2 C11 H11 118.8 . . ? C14 C12 C9 120.8(5) . . ? C14 C12 H12 119.6 . . ? C9 C12 H12 119.6 . . ? C30 C13 C21 121.4(5) . . ? C30 C13 H13 119.3 . . ? C21 C13 H13 119.3 . . ? C12 C14 C22 122.6(5) . . ? C12 C14 H14 118.7 . . ? C22 C14 H14 118.7 . . ? C35 C15 C29 118.2(5) . . ? C35 C15 N3 124.2(5) . . ? C29 C15 N3 117.5(5) . . ? C23 C16 C37 120.2(5) . . ? C23 C16 C42 119.5(5) . . ? C37 C16 C42 120.2(5) . . ? C33 C17 C20 119.8(5) . . ? C33 C17 H17 120.1 . . ? C20 C17 H17 120.1 . . ? C32 C18 C27 120.1(5) . . ? C32 C18 H18 120.0 . . ? C27 C18 H18 120.0 . . ? O3 C19 O4 121.4(5) . . ? O3 C19 C8 125.6(5) . . ? O4 C19 C8 112.8(5) . . ? C23 C20 N2 118.9(5) . . ? C23 C20 C17 118.4(5) . . ? N2 C20 C17 122.6(5) . . ? N2 C21 C13 121.7(5) . . ? N2 C21 C8 120.8(5) . . ? C13 C21 C8 117.4(5) . . ? C11 C22 C14 116.6(5) . . ? C11 C22 H22 121.7 . . ? C14 C22 H22 121.7 . . ? C20 C23 C16 120.7(5) . . ? C20 C23 H23 119.7 . . ? C16 C23 H23 119.7 . . ? C38 C24 C27 120.0(5) . . ? C38 C24 H24 120.0 . . ? C27 C24 H24 120.0 . . ? C10 C25 C7 120.8(5) . . ? C10 C25 H25 119.6 . . ? C7 C25 H25 119.6 . . ? C10 C26 C5 118.4(5) . . ? C10 C26 H26 120.8 . . ? C5 C26 H26 120.8 . . ? C18 C27 N1 118.6(5) . . ? C18 C27 C24 118.5(5) . . ? N1 C27 C24 122.8(5) . . ? C40 C28 C35 119.9(6) . . ? C40 C28 C41 121.1(6) . . ? C35 C28 C41 118.9(5) . . ? C34 C29 C15 121.5(6) . . ? C34 C29 H29 119.3 . . ? C15 C29 H29 119.3 . . ? C13 C30 C31 122.0(5) . . ? C13 C30 H30 119.0 . . ? C31 C30 H30 119.0 . . ? C6 C31 C30 116.7(5) . . ? C6 C31 H31 121.7 . . ? C30 C31 H31 121.7 . . ? C18 C32 C36 120.5(5) . . ? C18 C32 C39 120.8(5) . . ? C36 C32 C39 118.6(5) . . ? C37 C33 C17 122.0(5) . . ? C37 C33 H33 119.0 . . ? C17 C33 H33 119.0 . . ? C40 C34 C29 119.0(5) . . ? C40 C34 H34 120.5 . . ? C29 C34 H34 120.5 . . ? C15 C35 C28 120.7(5) . . ? C15 C35 H35 119.7 . . ? C28 C35 H35 119.7 . . ? C38 C36 C32 120.0(5) . . ? C38 C36 H36 120.0 . . ? C32 C36 H36 120.0 . . ? C33 C37 C16 118.8(5) . . ? C33 C37 H37 120.6 . . ? C16 C37 H37 120.6 . . ? C36 C38 C24 120.7(5) . . ? C36 C38 H38 119.6 . . ? C24 C38 H38 119.6 . . ? F1 C39 F2 107.2(5) . . ? F1 C39 F7 106.4(5) . . ? F2 C39 F7 104.5(5) . . ? F1 C39 C32 112.7(5) . . ? F2 C39 C32 114.1(5) . . ? F7 C39 C32 111.4(5) . . ? C34 C40 C28 120.7(6) . . ? C34 C40 H40 119.6 . . ? C28 C40 H40 119.6 . . ? F8 C41 F5 105.7(5) . . ? F8 C41 F6 106.3(6) . . ? F5 C41 F6 105.3(6) . . ? F8 C41 C28 111.8(5) . . ? F5 C41 C28 112.4(6) . . ? F6 C41 C28 114.7(5) . . ? F3 C42 F4 105.9(5) . . ? F3 C42 F9 105.7(6) . . ? F4 C42 F9 104.5(5) . . ? F3 C42 C16 113.8(5) . . ? F4 C42 C16 113.6(5) . . ? F9 C42 C16 112.6(5) . . ? C51 N4 C49 117.6(4) . . ? C52 N5 C48 116.8(4) . . ? C48 C43 C50 120.2(5) . . ? C48 C43 H43 119.9 . . ? C50 C43 H43 119.9 . . ? C45 C44 C49 119.8(5) . . ? C45 C44 H44 120.1 . . ? C49 C44 H44 120.1 . . ? C44 C45 C47 117.2(5) . . ? C44 C45 C50 121.3(5) . . ? C47 C45 C50 121.4(5) . . ? C52 C46 C50 120.9(5) . . ? C52 C46 H46 119.6 . . ? C50 C46 H46 119.6 . . ? C51 C47 C45 120.0(5) . . ? C51 C47 H47 120.0 . . ? C45 C47 H47 120.0 . . ? N5 C48 C43 123.4(5) . . ? N5 C48 H48 118.3 . . ? C43 C48 H48 118.3 . . ? N4 C49 C44 122.6(5) . . ? N4 C49 H49 118.7 . . ? C44 C49 H49 118.7 . . ? C46 C50 C43 114.7(4) . . ? C46 C50 C45 122.9(5) . . ? C43 C50 C45 122.4(5) . . ? N4 C51 C47 122.7(5) . . ? N4 C51 H51 118.6 . . ? C47 C51 H51 118.6 . . ? N5 C52 C46 123.9(5) . . ? N5 C52 H52 118.1 . . ? C46 C52 H52 118.0 . . ? C55 N6 C57 116.0(4) . . ? C55 C54 C53 118.1(5) . . ? C55 C54 H54 121.0 . . ? C53 C54 H54 121.0 . . ? C56 C53 C54 116.3(4) . . ? C56 C53 C53 123.4(6) . 2_655 ? C54 C53 C53 120.3(5) . 2_655 ? N6 C55 C54 125.7(5) . . ? N6 C55 H55 117.1 . . ? C54 C55 H55 117.1 . . ? C53 C56 C57 119.4(5) . . ? C53 C56 H56 120.3 . . ? C57 C56 H56 120.3 . . ? N6 C57 C56 124.4(5) . . ? N6 C57 H57 117.8 . . ? C56 C57 H57 117.8 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.915 _refine_diff_density_min -0.533 _refine_diff_density_rms 0.183 # start Validation Reply Form _vrf_DIFMX01_FFA-BP ; PROBLEM: The maximum difference density is > 0.1*ZMAX*2.00 RESPONSE: This could be due to poor diffraction data, which did not allow us to locate the H-atoms on O and N atoms from difference map.Therefore, these H-atoms were positioned geometrically. ; _vrf_RFACR01_FFA-BP ; PROBLEM: The value of the weighted R factor is > 0.45 RESPONSE: All our attempts to obtain bigger crystals were not successful and the diffraction data was collected on a very thin needle crystal that resulted a poor diffraction data. Crystal structure confirmed the expected structure, however, resulted in high R-factor. ; _vrf_RFACG01_FFA-BP ; PROBLEM: The value of the R factor is > 0.15 RESPONSE: All our attempts to obtain bigger crystals were not successful and the diffraction data was collected on a very thin needle crystal that resulted a poor diffraction data. Crystal structure confirmed the expected structure, however, resulted in high R-factor. ; _vrf_PLAT084_FFA-BP ; PROBLEM: High wR2 Value (i.e. > 0.25) ................... 0.50 RESPONSE: All our attempts to obtain bigger crystals were not successful and the diffraction data was collected on a very thin needle crystal that resulted a poor diffraction data. Crystal structure confirmed the expected structure, however, resulted in high R-factor. ; _vrf_PLAT097_FFA-BP ; PROBLEM: Large Reported Max. (Positive) Residual Density 1.91 eA-3 RESPONSE: This could be due to poor diffraction data, which did not allow us to locate the H-atoms on O and N atoms from difference map. Therefore, these H-atoms were positioned geometrically. ; _vrf_PLAT082_FFA-BP ; PROBLEM: High R1 Value .................................. 0.20 RESPONSE: All our attempts to obtain bigger crystals were not successful and the diffraction data was collected on a very thin needle crystal that resulted a poor diffraction data. Crystal structure confirmed the expected structure, however, resulted in high R-factor. ; _vrf_PLAT230_FFA-BP ; PROBLEM: Hirshfeld Test Diff for O3 -- C19 .. 7.7 su RESPONSE: There could be some positional disorder at this site which was not accounted in the stucture solution. ; # end Validation Reply Form #====END _database_code_depnum_ccdc_archive 'CCDC 960222'