# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_x _database_code_depnum_ccdc_archive 'CCDC 890901' #TrackingRef 'CPQT-OH.CIF' _audit_update_record ; 2011-01-29 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H34 F24 N4 O P4' _chemical_formula_weight 1130.56 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 7.692(3) _cell_length_b 20.230(7) _cell_length_c 14.097(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.130(9) _cell_angle_gamma 90.00 _cell_volume 2187.9(14) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.716 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 0.314 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ? _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13065 _diffrn_reflns_av_R_equivalents 0.1073 _diffrn_reflns_av_sigmaI/netI 0.1324 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4309 _reflns_number_gt 1527 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0200P)^2^+4.0000P] 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 4309 _refine_ls_number_parameters 437 _refine_ls_number_restraints 665 _refine_ls_R_factor_all 0.2205 _refine_ls_R_factor_gt 0.0744 _refine_ls_wR_factor_ref 0.1699 _refine_ls_wR_factor_gt 0.1323 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.004 _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 P1 P -0.1107(2) 0.08284(9) 0.11464(13) 0.0605(5) Uani 1 1 d . . . F1 F -0.1246(6) 0.16065(18) 0.1170(3) 0.1099(14) Uani 1 1 d . . . F2 F -0.3143(4) 0.0779(2) 0.1060(3) 0.1048(14) Uani 1 1 d . . . F3 F -0.1040(5) 0.0866(2) 0.0038(2) 0.1027(14) Uani 1 1 d . . . F4 F -0.0930(5) 0.00555(18) 0.1160(3) 0.1158(16) Uani 1 1 d . . . F5 F 0.0943(4) 0.0884(2) 0.1242(3) 0.0943(13) Uani 1 1 d . . . F6 F -0.1137(5) 0.0816(2) 0.2267(3) 0.1065(14) Uani 1 1 d . . . N1 N 0.5775(10) -0.2197(3) -0.0276(4) 0.094(2) Uani 1 1 d D . . N2 N 0.4722(8) 0.0219(3) 0.3144(4) 0.0832(18) Uani 1 1 d . . . C1 C 0.7040(11) -0.1765(4) -0.0061(6) 0.112(3) Uani 1 1 d . . . H1A H 0.8028 -0.1766 -0.0404 0.134 Uiso 1 1 calc R . . C2 C 0.6914(10) -0.1325(4) 0.0647(5) 0.088(2) Uani 1 1 d . . . H2A H 0.7841 -0.1042 0.0809 0.105 Uiso 1 1 calc R . . C3 C 0.5430(9) -0.1290(3) 0.1132(5) 0.0653(18) Uani 1 1 d . . . C4 C 0.4125(8) -0.1746(3) 0.0890(5) 0.072(2) Uani 1 1 d . . . H4A H 0.3111 -0.1746 0.1211 0.086 Uiso 1 1 calc R . . C5 C 0.4320(10) -0.2197(4) 0.0178(6) 0.082(2) Uani 1 1 d . . . H5A H 0.3442 -0.2501 0.0016 0.099 Uiso 1 1 calc R . . C6 C 0.5202(8) -0.0775(3) 0.1854(4) 0.0621(17) Uani 1 1 d . . . C7 C 0.6489(8) -0.0602(3) 0.2527(5) 0.0654(19) Uani 1 1 d . . . H7A H 0.7550 -0.0825 0.2547 0.078 Uiso 1 1 calc R . . C8 C 0.6255(9) -0.0110(3) 0.3173(5) 0.071(2) Uani 1 1 d . . . H8A H 0.7144 -0.0002 0.3629 0.086 Uiso 1 1 calc R . . C9 C 0.3441(10) 0.0046(4) 0.2497(6) 0.094(2) Uani 1 1 d . . . H9A H 0.2380 0.0267 0.2495 0.113 Uiso 1 1 calc R . . C10 C 0.3627(9) -0.0437(3) 0.1845(5) 0.078(2) Uani 1 1 d . . . H10A H 0.2717 -0.0541 0.1400 0.094 Uiso 1 1 calc R . . C11 C 0.4478(11) 0.0773(4) 0.3808(5) 0.106(3) Uani 1 1 d . . . H11A H 0.5535 0.0858 0.4193 0.127 Uiso 1 1 d R . . H11B H 0.3564 0.0672 0.4214 0.127 Uiso 1 1 d R . . C12 C 0.3926(14) 0.1378(5) 0.3187(7) 0.063(4) Uani 0.50 1 d PGDU . . C13 C 0.4621(10) 0.1676(5) 0.2410(7) 0.067(3) Uani 0.50 1 d PGDU . . H13A H 0.5669 0.1504 0.2172 0.080 Uiso 0.50 1 d PR . . C14 C 0.3800(14) 0.2221(6) 0.1978(8) 0.060(4) Uani 0.50 1 d PGDU . . C15 C 0.2283(14) 0.2469(5) 0.2323(9) 0.080(4) Uani 0.50 1 d PGDU . . H15A H 0.1715 0.2846 0.2025 0.096 Uiso 0.50 1 d PR . . C16 C 0.1587(9) 0.2172(5) 0.3100(7) 0.082(3) Uani 0.50 1 d PGDU . . C17 C 0.2409(14) 0.1626(6) 0.3532(6) 0.058(5) Uani 0.50 1 d PGD . . H17A H 0.1929 0.1421 0.4069 0.070 Uiso 0.50 1 d PR . . C19 C 0.6288(17) -0.2677(10) -0.1051(13) 0.096(9) Uani 0.50 1 d PD . . H19A H 0.5249 -0.2941 -0.1100 0.115 Uiso 0.50 1 d PR . . H19B H 0.7258 -0.2968 -0.0911 0.115 Uiso 0.50 1 d PR . . C19B C 0.454(3) 0.2624(7) 0.1167(8) 0.097(9) Uani 0.50 1 d PD . 2 H19C H 0.5347 0.2984 0.1246 0.117 Uiso 0.50 1 d PR . 2 H19D H 0.3384 0.2799 0.1031 0.117 Uiso 0.50 1 d PR . 2 C20 C 0.6086(11) -0.2384(4) -0.2003(8) 0.055(5) Uani 0.50 1 d PG . 2 C21 C 0.4480(9) -0.2106(4) -0.2287(7) 0.068(4) Uani 0.50 1 d PGD . 2 H21A H 0.3449 -0.2251 -0.2003 0.082 Uiso 0.50 1 d PR . 2 C22 C 0.4367(10) -0.1618(5) -0.2983(6) 0.062(4) Uani 0.50 1 d PG . 2 H22A H 0.3258 -0.1426 -0.3179 0.074 Uiso 0.50 1 d PR . 2 C23 C 0.5860(14) -0.1409(6) -0.3395(6) 0.055(5) Uani 0.50 1 d PG . 2 C24 C 0.7466(11) -0.1687(6) -0.3111(7) 0.056(4) Uani 0.50 1 d PG . 2 H24A H 0.8497 -0.1542 -0.3396 0.067 Uiso 0.50 1 d PR . 2 C25 C 0.7579(9) -0.2175(5) -0.2415(8) 0.076(5) Uani 0.50 1 d PGD . 2 H25A H 0.8689 -0.2367 -0.2219 0.091 Uiso 0.50 1 d PR . 2 C18 C -0.0067(16) 0.2482(10) 0.3417(16) 0.091(5) Uani 0.25 1 d PDU . 1 H18A H -0.1041 0.2216 0.3161 0.109 Uiso 0.25 1 calc PR . 1 H18B H -0.0037 0.2448 0.4104 0.109 Uiso 0.25 1 calc PR . 1 O1 O -0.040(3) 0.3108(11) 0.3183(17) 0.132(7) Uani 0.25 1 d PDU . 1 H1B H -0.0508 0.3346 0.2684 0.198 Uiso 0.25 1 d PR . 1 C18B C 0.0033(18) 0.2269(12) 0.3695(14) 0.109(6) Uani 0.25 1 d PDU . 2 H18C H -0.0205 0.1869 0.4043 0.131 Uiso 0.25 1 calc PR . 2 H18D H 0.0247 0.2628 0.4145 0.131 Uiso 0.25 1 calc PR . 2 O1B O -0.130(3) 0.2414(12) 0.3067(16) 0.138(7) Uani 0.25 1 d PDU . 2 H1BA H -0.1290 0.2196 0.2553 0.207 Uiso 0.25 1 d PR . 2 P2 P 0.1039(3) -0.38971(10) -0.07281(17) 0.0994(8) Uani 1 1 d D . . F7 F 0.0658(15) -0.3750(7) -0.1813(5) 0.143(4) Uani 0.606(10) 1 d PDU A 1 F8 F 0.0988(15) -0.4650(3) -0.0956(9) 0.139(4) Uani 0.606(10) 1 d PDU A 1 F9 F 0.1232(11) -0.4058(6) 0.0353(4) 0.132(3) Uani 0.606(10) 1 d PDU A 1 F10 F 0.0922(17) -0.3145(3) -0.0503(10) 0.164(4) Uani 0.606(10) 1 d PDU A 1 F11 F 0.3053(8) -0.3907(8) -0.0762(8) 0.151(4) Uani 0.606(10) 1 d PDU A 1 F12 F -0.0892(10) -0.4009(8) -0.0534(17) 0.132(5) Uani 0.606(10) 1 d PDU A 1 F7B F 0.081(3) -0.3190(5) -0.1160(15) 0.156(5) Uani 0.394(10) 1 d PDU A 2 F8B F 0.057(2) -0.4211(9) -0.1720(8) 0.135(5) Uani 0.394(10) 1 d PDU A 2 F9B F 0.180(2) -0.4574(5) -0.0361(12) 0.158(5) Uani 0.394(10) 1 d PDU A 2 F10B F 0.179(2) -0.3563(9) 0.0210(10) 0.154(5) Uani 0.394(10) 1 d PDU A 2 F11B F 0.2847(13) -0.3719(9) -0.1113(15) 0.148(5) Uani 0.394(10) 1 d PDU A 2 F12B F -0.0976(12) -0.3815(15) -0.067(3) 0.136(6) Uani 0.394(10) 1 d PDU A 2 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 P1 0.0443(10) 0.0675(12) 0.0698(13) -0.0030(10) 0.0041(8) -0.0020(9) F1 0.117(3) 0.065(3) 0.148(4) -0.003(3) 0.012(3) -0.001(3) F2 0.038(2) 0.136(4) 0.141(4) -0.011(3) 0.009(2) -0.010(2) F3 0.082(3) 0.161(4) 0.064(3) -0.007(3) 0.000(2) 0.014(3) F4 0.104(3) 0.061(3) 0.187(4) -0.008(3) 0.041(3) -0.005(2) F5 0.042(2) 0.124(3) 0.116(3) 0.042(3) -0.001(2) -0.008(2) F6 0.112(3) 0.138(4) 0.071(3) 0.001(3) 0.018(2) -0.012(3) N1 0.133(6) 0.091(5) 0.061(4) -0.003(4) 0.015(4) -0.062(5) N2 0.088(5) 0.071(4) 0.084(4) -0.006(3) -0.042(4) 0.003(4) C1 0.136(8) 0.120(7) 0.083(6) -0.020(5) 0.029(5) -0.093(6) C2 0.094(6) 0.104(6) 0.065(5) 0.001(5) 0.004(4) -0.061(5) C3 0.071(5) 0.063(5) 0.059(4) 0.025(4) -0.016(4) -0.021(4) C4 0.059(4) 0.067(5) 0.086(6) 0.017(4) -0.020(4) -0.021(4) C5 0.091(6) 0.068(5) 0.085(6) 0.012(5) -0.010(5) -0.035(5) C6 0.060(4) 0.061(4) 0.062(4) 0.028(4) -0.018(3) -0.014(4) C7 0.050(4) 0.075(5) 0.068(5) 0.023(4) -0.017(4) -0.011(3) C8 0.066(5) 0.070(5) 0.072(5) 0.011(4) -0.037(4) -0.010(4) C9 0.071(5) 0.079(5) 0.126(7) -0.006(5) -0.044(5) 0.006(4) C10 0.082(5) 0.066(5) 0.079(5) 0.004(4) -0.045(4) -0.011(4) C11 0.123(7) 0.079(6) 0.106(6) -0.017(5) -0.055(5) 0.004(5) C12 0.044(8) 0.069(9) 0.075(9) -0.025(7) 0.006(7) 0.006(7) C13 0.055(7) 0.066(8) 0.082(9) -0.039(7) 0.017(7) 0.011(6) C14 0.048(9) 0.051(7) 0.082(10) -0.027(7) 0.016(8) -0.007(6) C15 0.063(8) 0.074(8) 0.105(9) -0.034(7) 0.025(7) 0.006(6) C16 0.061(7) 0.088(8) 0.101(8) -0.028(7) 0.030(6) 0.014(6) C17 0.069(10) 0.100(12) 0.007(8) -0.005(7) 0.008(7) 0.019(8) C19 0.028(9) 0.119(15) 0.14(2) -0.041(14) -0.012(9) -0.039(9) C19B 0.097(17) 0.150(19) 0.046(11) -0.023(11) 0.015(10) -0.108(14) C20 0.054(12) 0.040(9) 0.065(11) -0.017(8) -0.035(10) 0.001(8) C21 0.068(10) 0.060(10) 0.073(10) -0.021(8) -0.010(8) 0.000(8) C22 0.054(9) 0.069(10) 0.061(9) -0.031(8) -0.004(7) 0.003(7) C23 0.049(11) 0.087(13) 0.029(8) -0.003(8) -0.004(7) -0.006(9) C24 0.070(11) 0.082(12) 0.015(9) -0.017(8) 0.002(8) -0.020(8) C25 0.050(10) 0.056(11) 0.118(15) -0.034(10) -0.010(10) 0.009(8) C18 0.064(10) 0.089(10) 0.119(11) -0.006(10) 0.010(9) 0.021(9) O1 0.104(13) 0.136(14) 0.155(14) -0.018(14) 0.005(12) 0.031(12) C18B 0.080(10) 0.112(10) 0.137(11) -0.009(10) 0.015(9) 0.016(10) O1B 0.110(14) 0.165(15) 0.139(14) -0.044(13) 0.001(13) 0.032(13) P2 0.0901(18) 0.0809(17) 0.120(2) 0.0175(14) -0.0450(14) -0.0256(13) F7 0.171(7) 0.139(8) 0.116(6) 0.037(6) -0.025(6) -0.031(7) F8 0.143(7) 0.088(6) 0.185(9) -0.017(6) 0.001(7) -0.017(5) F9 0.141(7) 0.166(9) 0.084(5) 0.043(5) -0.032(5) 0.007(6) F10 0.199(8) 0.089(6) 0.191(10) -0.002(6) -0.074(8) -0.041(6) F11 0.097(6) 0.190(9) 0.161(9) 0.056(7) -0.033(5) -0.034(6) F12 0.095(7) 0.128(10) 0.171(10) -0.003(8) -0.009(7) -0.031(5) F7B 0.190(10) 0.105(9) 0.164(11) 0.052(8) -0.044(10) -0.006(8) F8B 0.107(8) 0.153(11) 0.134(9) -0.032(8) -0.063(7) -0.017(9) F9B 0.174(10) 0.108(9) 0.178(11) 0.023(8) -0.077(9) -0.005(8) F10B 0.155(9) 0.148(10) 0.150(10) -0.006(9) -0.060(8) -0.009(9) F11B 0.105(9) 0.148(11) 0.187(11) 0.025(9) -0.022(8) -0.067(8) F12B 0.107(9) 0.145(12) 0.148(10) 0.020(10) -0.047(8) 0.015(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 F2 1.565(4) . ? P1 F3 1.569(4) . ? P1 F4 1.569(4) . ? P1 F5 1.576(4) . ? P1 F1 1.578(4) . ? P1 F6 1.582(4) . ? N1 C1 1.327(8) . ? N1 C5 1.329(8) . ? N1 C19B 1.529(10) 3_655 ? N1 C19 1.533(11) . ? N2 C9 1.340(8) . ? N2 C8 1.351(8) . ? N2 C11 1.481(8) . ? C1 C2 1.345(9) . ? C1 H1A 0.9300 . ? C2 C3 1.374(8) . ? C2 H2A 0.9300 . ? C3 C4 1.389(8) . ? C3 C6 1.475(8) . ? C4 C5 1.372(8) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 C7 1.366(8) . ? C6 C10 1.390(8) . ? C7 C8 1.371(8) . ? C7 H7A 0.9300 . ? C8 H8A 0.9300 . ? C9 C10 1.357(9) . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C11 C23 1.43(7) 3_655 ? C11 C12 1.547(11) . ? C11 H11A 0.9600 . ? C11 H11B 0.9601 . ? C12 C23 0.33(5) 3_655 ? C12 C24 1.24(5) 3_655 ? C12 C13 1.3900 . ? C12 C17 1.3900 . ? C12 C22 1.45(6) 3_655 ? C13 C22 1.09(6) 3_655 ? C13 C21 1.13(6) 3_655 ? C13 C14 1.3900 . ? C13 C23 1.56(6) 3_655 ? C13 C20 1.624(15) 3_655 ? C13 C24 1.95(5) 3_655 ? C13 C25 1.97(5) 3_655 ? C13 H13A 0.9599 . ? C14 C20 0.343(17) 3_655 ? C14 C25 1.27(5) 3_655 ? C14 C21 1.38(6) 3_655 ? C14 C15 1.3900 . ? C14 C19B 1.544(10) . ? C14 C19 1.60(3) 3_655 ? C15 C25 0.62(6) 3_655 ? C15 C20 1.374(14) 3_655 ? C15 C16 1.3900 . ? C15 C24 1.94(7) 3_655 ? C15 H15A 0.9601 . ? C16 C25 1.20(5) 3_655 ? C16 C24 1.22(5) 3_655 ? C16 C17 1.3900 . ? C16 C18 1.514(10) . ? C16 C18B 1.522(10) . ? C17 C24 0.62(6) 3_655 ? C17 C23 1.43(5) 3_655 ? C17 C25 1.93(7) 3_655 ? C17 H17A 0.9600 . ? C19 C19B 0.65(3) 3_655 ? C19 C20 1.47(2) . ? C19 C14 1.60(8) 3_655 ? C19 H19A 0.9599 . ? C19 H19B 0.9601 . ? C19B C19 0.65(3) 3_655 ? C19B C20 1.391(15) 3_655 ? C19B N1 1.529(10) 3_655 ? C19B C21 2.00(7) 3_655 ? C19B H19C 0.9600 . ? C19B H19D 0.9599 . ? C20 C14 0.34(5) 3_655 ? C20 C15 1.37(4) 3_655 ? C20 C21 1.3900 . ? C20 C25 1.3900 . ? C20 C19B 1.391(15) 3_655 ? C20 C13 1.62(7) 3_655 ? C21 C13 1.13(6) 3_655 ? C21 C14 1.38(6) 3_655 ? C21 C22 1.3900 . ? C21 C19B 2.00(2) 3_655 ? C21 H21A 0.9600 . ? C22 C13 1.09(6) 3_655 ? C22 C23 1.3900 . ? C22 C12 1.448(18) 3_655 ? C22 H22A 0.9599 . ? C23 C12 0.332(17) 3_655 ? C23 C24 1.3900 . ? C23 C11 1.427(11) 3_655 ? C23 C17 1.43(4) 3_655 ? C23 C13 1.56(7) 3_655 ? C24 C17 0.62(7) 3_655 ? C24 C16 1.22(5) 3_655 ? C24 C12 1.237(15) 3_655 ? C24 C25 1.3900 . ? C24 C15 1.94(8) 3_655 ? C24 C13 1.95(4) 3_655 ? C24 H24A 0.9600 . ? C25 C15 0.62(7) 3_655 ? C25 C16 1.20(5) 3_655 ? C25 C14 1.27(5) 3_655 ? C25 C17 1.93(8) 3_655 ? C25 C13 1.97(5) 3_655 ? C25 H25A 0.9600 . ? C18 O1 1.331(10) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? O1 H1B 0.8500 . ? C18B O1B 1.336(10) . ? C18B H18C 0.9700 . ? C18B H18D 0.9700 . ? O1B H1BA 0.8497 . ? P2 F12 1.546(6) . ? P2 F11 1.554(6) . ? P2 F9 1.555(5) . ? P2 F8B 1.555(6) . ? P2 F8 1.557(5) . ? P2 F10 1.557(5) . ? P2 F10B 1.559(6) . ? P2 F7B 1.560(6) . ? P2 F9B 1.563(6) . ? P2 F7 1.565(5) . ? P2 F12B 1.567(7) . ? P2 F11B 1.571(6) . ? 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 F2 P1 F3 91.7(2) . . ? F2 P1 F4 91.3(2) . . ? F3 P1 F4 92.9(3) . . ? F2 P1 F5 179.4(3) . . ? F3 P1 F5 88.7(2) . . ? F4 P1 F5 89.1(2) . . ? F2 P1 F1 89.8(2) . . ? F3 P1 F1 88.9(3) . . ? F4 P1 F1 177.9(3) . . ? F5 P1 F1 89.8(2) . . ? F2 P1 F6 89.4(2) . . ? F3 P1 F6 177.9(3) . . ? F4 P1 F6 88.9(3) . . ? F5 P1 F6 90.1(2) . . ? F1 P1 F6 89.3(3) . . ? C1 N1 C5 121.3(7) . . ? C1 N1 C19B 129.0(8) . 3_655 ? C5 N1 C19B 108.0(9) . 3_655 ? C1 N1 C19 111.0(8) . . ? C5 N1 C19 127.7(8) . . ? C19B N1 C19 24.6(10) 3_655 . ? C9 N2 C8 119.3(6) . . ? C9 N2 C11 120.5(6) . . ? C8 N2 C11 120.2(6) . . ? N1 C1 C2 121.0(7) . . ? N1 C1 H1A 119.5 . . ? C2 C1 H1A 119.5 . . ? C1 C2 C3 120.7(7) . . ? C1 C2 H2A 119.7 . . ? C3 C2 H2A 119.7 . . ? C2 C3 C4 117.1(7) . . ? C2 C3 C6 121.6(6) . . ? C4 C3 C6 121.3(7) . . ? C5 C4 C3 120.4(7) . . ? C5 C4 H4A 119.8 . . ? C3 C4 H4A 119.8 . . ? N1 C5 C4 119.5(7) . . ? N1 C5 H5A 120.3 . . ? C4 C5 H5A 120.3 . . ? C7 C6 C10 117.9(7) . . ? C7 C6 C3 122.9(6) . . ? C10 C6 C3 119.2(6) . . ? C6 C7 C8 121.6(6) . . ? C6 C7 H7A 119.2 . . ? C8 C7 H7A 119.2 . . ? N2 C8 C7 119.6(6) . . ? N2 C8 H8A 120.2 . . ? C7 C8 H8A 120.2 . . ? N2 C9 C10 122.7(7) . . ? N2 C9 H9A 118.6 . . ? C10 C9 H9A 118.6 . . ? C9 C10 C6 118.8(6) . . ? C9 C10 H10A 120.6 . . ? C6 C10 H10A 120.6 . . ? C23 C11 N2 116.9(10) 3_655 . ? C23 C11 C12 12.0(14) 3_655 . ? N2 C11 C12 106.5(6) . . ? C23 C11 H11A 101.0 3_655 . ? N2 C11 H11A 110.6 . . ? C12 C11 H11A 111.4 . . ? C23 C11 H11B 108.4 3_655 . ? N2 C11 H11B 110.3 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 109.1 . . ? C23 C12 C24 111(6) 3_655 3_655 ? C23 C12 C13 115(10) 3_655 . ? C24 C12 C13 95(3) 3_655 . ? C23 C12 C17 90(8) 3_655 . ? C24 C12 C17 26(3) 3_655 . ? C13 C12 C17 120.0 . . ? C23 C12 C22 73(9) 3_655 3_655 ? C24 C12 C22 127(5) 3_655 3_655 ? C13 C12 C22 45(2) . 3_655 ? C17 C12 C22 138.1(14) . 3_655 ? C23 C12 C11 63(10) 3_655 . ? C24 C12 C11 130(3) 3_655 . ? C13 C12 C11 133.1(8) . . ? C17 C12 C11 106.9(8) . . ? C22 C12 C11 99(3) 3_655 . ? C22 C13 C21 78(3) 3_655 3_655 ? C22 C13 C12 70(3) 3_655 . ? C21 C13 C12 137(2) 3_655 . ? C22 C13 C14 134(2) 3_655 . ? C21 C13 C14 66(3) 3_655 . ? C12 C13 C14 120.0 . . ? C22 C13 C23 60(3) 3_655 3_655 ? C21 C13 C23 126(2) 3_655 3_655 ? C12 C13 C23 11.1(18) . 3_655 ? C14 C13 C23 122.4(19) . 3_655 ? C22 C13 C20 124(3) 3_655 3_655 ? C21 C13 C20 57(3) 3_655 3_655 ? C12 C13 C20 121.5(5) . 3_655 ? C14 C13 C20 9.6(8) . 3_655 ? C23 C13 C20 122(2) 3_655 3_655 ? C22 C13 C24 101(3) 3_655 3_655 ? C21 C13 C24 127.1(18) 3_655 3_655 ? C12 C13 C24 39(2) . 3_655 ? C14 C13 C24 81(2) . 3_655 ? C23 C13 C24 45.1(13) 3_655 3_655 ? C20 C13 C24 84(2) 3_655 3_655 ? C22 C13 C25 128.4(16) 3_655 3_655 ? C21 C13 C25 98(3) 3_655 3_655 ? C12 C13 C25 81(2) . 3_655 ? C14 C13 C25 40(2) . 3_655 ? C23 C13 C25 85(2) 3_655 3_655 ? C20 C13 C25 44(2) 3_655 3_655 ? C24 C13 C25 41.6(10) 3_655 3_655 ? C22 C13 H13A 69.4 3_655 . ? C21 C13 H13A 71.8 3_655 . ? C12 C13 H13A 120.0 . . ? C14 C13 H13A 120.0 . . ? C23 C13 H13A 116.5 3_655 . ? C20 C13 H13A 117.6 3_655 . ? C24 C13 H13A 157.9 3_655 . ? C25 C13 H13A 158.3 3_655 . ? C20 C14 C25 104(4) 3_655 3_655 ? C20 C14 C21 84(4) 3_655 3_655 ? C25 C14 C21 130(5) 3_655 3_655 ? C20 C14 C15 80(2) 3_655 . ? C25 C14 C15 26(3) 3_655 . ? C21 C14 C15 139.4(14) 3_655 . ? C20 C14 C13 128(3) 3_655 . ? C25 C14 C13 96(3) 3_655 . ? C21 C14 C13 48(3) 3_655 . ? C15 C14 C13 120.0 . . ? C20 C14 C19B 58(3) 3_655 . ? C25 C14 C19B 140(3) 3_655 . ? C21 C14 C19B 86(3) 3_655 . ? C15 C14 C19B 115.5(11) . . ? C13 C14 C19B 124.3(11) . . ? C20 C14 C19 62(3) 3_655 3_655 ? C25 C14 C19 117(3) 3_655 3_655 ? C21 C14 C19 110(3) 3_655 3_655 ? C15 C14 C19 95.2(8) . 3_655 ? C13 C14 C19 143.9(8) . 3_655 ? C19B C14 C19 23.8(9) . 3_655 ? C25 C15 C20 79(5) 3_655 3_655 ? C25 C15 C14 66(5) 3_655 . ? C20 C15 C14 14.2(7) 3_655 . ? C25 C15 C16 59(4) 3_655 . ? C20 C15 C16 128.1(7) 3_655 . ? C14 C15 C16 120.0 . . ? C25 C15 C24 23(4) 3_655 3_655 ? C20 C15 C24 91.8(16) 3_655 3_655 ? C14 C15 C24 81.6(13) . 3_655 ? C16 C15 C24 38.9(11) . 3_655 ? C25 C15 H15A 157.5 3_655 . ? C20 C15 H15A 110.6 3_655 . ? C14 C15 H15A 120.0 . . ? C16 C15 H15A 120.0 . . ? C24 C15 H15A 157.5 3_655 . ? C25 C16 C24 70.2(17) 3_655 3_655 ? C25 C16 C15 26(3) 3_655 . ? C24 C16 C15 95(3) 3_655 . ? C25 C16 C17 96(3) 3_655 . ? C24 C16 C17 26(3) 3_655 . ? C15 C16 C17 120.0 . . ? C25 C16 C18 138(3) 3_655 . ? C24 C16 C18 147(3) 3_655 . ? C15 C16 C18 115.6(13) . . ? C17 C16 C18 124.4(13) . . ? C25 C16 C18B 159(3) 3_655 . ? C24 C16 C18B 126(3) 3_655 . ? C15 C16 C18B 137.7(13) . . ? C17 C16 C18B 102.3(13) . . ? C18 C16 C18B 22.1(16) . . ? C24 C17 C16 61(5) 3_655 . ? C24 C17 C12 63(5) 3_655 . ? C16 C17 C12 120.0 . . ? C24 C17 C23 74(4) 3_655 3_655 ? C16 C17 C23 126(3) . 3_655 ? C12 C17 C23 13.4(15) . 3_655 ? C24 C17 C25 25(4) 3_655 3_655 ? C16 C17 C25 38.2(11) . 3_655 ? C12 C17 C25 82.4(13) . 3_655 ? C23 C17 C25 90(3) 3_655 3_655 ? C24 C17 H17A 159.1 3_655 . ? C16 C17 H17A 120.0 . . ? C12 C17 H17A 120.0 . . ? C23 C17 H17A 112.9 3_655 . ? C25 C17 H17A 156.6 3_655 . ? C19B C19 C20 71(3) 3_655 . ? C19B C19 N1 77.3(10) 3_655 . ? C20 C19 N1 112.4(14) . . ? C19B C19 C14 74(3) 3_655 3_655 ? C20 C19 C14 11.9(11) . 3_655 ? N1 C19 C14 102.7(13) . 3_655 ? C19B C19 H19A 44.2 3_655 . ? C20 C19 H19A 97.2 . . ? N1 C19 H19A 98.6 . . ? C14 C19 H19A 106.0 3_655 . ? C19B C19 H19B 151.5 3_655 . ? C20 C19 H19B 117.7 . . ? N1 C19 H19B 118.6 . . ? C14 C19 H19B 120.6 3_655 . ? H19A C19 H19B 107.6 . . ? C19 C19B C20 83(2) 3_655 3_655 ? C19 C19B N1 78.1(10) 3_655 3_655 ? C20 C19B N1 117.2(9) 3_655 3_655 ? C19 C19B C14 83(3) 3_655 . ? C20 C19B C14 12.0(8) 3_655 . ? N1 C19B C14 105.4(9) 3_655 . ? C19 C19B C21 126(3) 3_655 3_655 ? C20 C19B C21 44.0(17) 3_655 3_655 ? N1 C19B C21 112.4(11) 3_655 3_655 ? C14 C19B C21 43.6(18) . 3_655 ? C19 C19B H19C 121.2 3_655 . ? C20 C19B H19C 115.2 3_655 . ? N1 C19B H19C 125.8 3_655 . ? C14 C19B H19C 125.7 . . ? C21 C19B H19C 95.7 3_655 . ? C19 C19B H19D 12.5 3_655 . ? C20 C19B H19D 85.9 3_655 . ? N1 C19B H19D 87.6 3_655 . ? C14 C19B H19D 87.7 . . ? C21 C19B H19D 130.0 3_655 . ? H19C C19B H19D 109.1 . . ? C14 C20 C15 86(8) 3_655 3_655 ? C14 C20 C21 82(10) 3_655 . ? C15 C20 C21 140(3) 3_655 . ? C14 C20 C25 62(7) 3_655 . ? C15 C20 C25 26(3) 3_655 . ? C21 C20 C25 120.0 . . ? C14 C20 C19B 110(9) 3_655 3_655 ? C15 C20 C19B 128(4) 3_655 3_655 ? C21 C20 C19B 91.9(11) . 3_655 ? C25 C20 C19B 143.6(10) . 3_655 ? C14 C20 C19 107(10) 3_655 . ? C15 C20 C19 102(3) 3_655 . ? C21 C20 C19 117.4(4) . . ? C25 C20 C19 118.0(4) . . ? C19B C20 C19 26.2(10) 3_655 . ? C14 C20 C13 42(10) 3_655 3_655 ? C15 C20 C13 107(5) 3_655 3_655 ? C21 C20 C13 43.3(17) . 3_655 ? C25 C20 C13 81.3(18) . 3_655 ? C19B C20 C13 118.7(16) 3_655 3_655 ? C19 C20 C13 133.7(13) . 3_655 ? C13 C21 C14 66(3) 3_655 3_655 ? C13 C21 C22 50(3) 3_655 . ? C14 C21 C22 111(3) 3_655 . ? C13 C21 C20 79(3) 3_655 . ? C14 C21 C20 14(2) 3_655 . ? C22 C21 C20 120.0 . . ? C13 C21 C19B 109(3) 3_655 3_655 ? C14 C21 C19B 50(3) 3_655 3_655 ? C22 C21 C19B 158.6(6) . 3_655 ? C20 C21 C19B 44.1(6) . 3_655 ? C13 C21 H21A 146.1 3_655 . ? C14 C21 H21A 128.2 3_655 . ? C22 C21 H21A 120.0 . . ? C20 C21 H21A 120.0 . . ? C19B C21 H21A 77.7 3_655 . ? C13 C22 C21 53(4) 3_655 . ? C13 C22 C23 77(3) 3_655 . ? C21 C22 C23 120.0 . . ? C13 C22 C12 65(3) 3_655 3_655 ? C21 C22 C12 111.5(5) . 3_655 ? C23 C22 C12 13.2(6) . 3_655 ? C13 C22 H22A 146.2 3_655 . ? C21 C22 H22A 120.0 . . ? C23 C22 H22A 120.0 . . ? C12 C22 H22A 127.4 3_655 . ? C12 C23 C22 93(3) 3_655 . ? C12 C23 C24 56(3) 3_655 . ? C22 C23 C24 120.0 . . ? C12 C23 C11 105(3) 3_655 3_655 ? C22 C23 C11 108.3(7) . 3_655 ? C24 C23 C11 127.9(7) . 3_655 ? C12 C23 C17 77(3) 3_655 3_655 ? C22 C23 C17 140(3) . 3_655 ? C24 C23 C17 25(3) . 3_655 ? C11 C23 C17 112(3) 3_655 3_655 ? C12 C23 C13 54(3) 3_655 3_655 ? C22 C23 C13 42.8(18) . 3_655 ? C24 C23 C13 82.3(19) . 3_655 ? C11 C23 C13 128.8(15) 3_655 3_655 ? C17 C23 C13 107(5) 3_655 3_655 ? C17 C24 C16 92(3) 3_655 3_655 ? C17 C24 C12 91(5) 3_655 3_655 ? C16 C24 C12 157(3) 3_655 3_655 ? C17 C24 C25 144(5) 3_655 . ? C16 C24 C25 54(3) 3_655 . ? C12 C24 C25 115.4(7) 3_655 . ? C17 C24 C23 81(5) 3_655 . ? C16 C24 C23 148(3) 3_655 . ? C12 C24 C23 12.9(8) 3_655 . ? C25 C24 C23 120.0 . . ? C17 C24 C15 134(5) 3_655 3_655 ? C16 C24 C15 46(3) 3_655 3_655 ? C12 C24 C15 120.8(17) 3_655 3_655 ? C25 C24 C15 10.1(7) . 3_655 ? C23 C24 C15 123.1(16) . 3_655 ? C17 C24 C13 132(7) 3_655 3_655 ? C16 C24 C13 121(5) 3_655 3_655 ? C12 C24 C13 45(2) 3_655 3_655 ? C25 C24 C13 70(2) . 3_655 ? C23 C24 C13 53(2) . 3_655 ? C15 C24 C13 77(3) 3_655 3_655 ? C17 C24 H24A 49.5 3_655 . ? C16 C24 H24A 75.0 3_655 . ? C12 C24 H24A 123.1 3_655 . ? C25 C24 H24A 120.0 . . ? C23 C24 H24A 120.0 . . ? C15 C24 H24A 116.0 3_655 . ? C13 C24 H24A 161.0 3_655 . ? C15 C25 C16 95(2) 3_655 3_655 ? C15 C25 C14 88(7) 3_655 3_655 ? C16 C25 C14 155(5) 3_655 3_655 ? C15 C25 C24 147(5) 3_655 . ? C16 C25 C24 56(3) 3_655 . ? C14 C25 C24 113(3) 3_655 . ? C15 C25 C20 76(5) 3_655 . ? C16 C25 C20 148(3) 3_655 . ? C14 C25 C20 13.9(19) 3_655 . ? C24 C25 C20 120.0 . . ? C15 C25 C17 136(4) 3_655 3_655 ? C16 C25 C17 46(3) 3_655 3_655 ? C14 C25 C17 120(4) 3_655 3_655 ? C24 C25 C17 10.9(7) . 3_655 ? C20 C25 C17 124.7(16) . 3_655 ? C15 C25 C13 129(6) 3_655 3_655 ? C16 C25 C13 121(5) 3_655 3_655 ? C14 C25 C13 44.6(16) 3_655 3_655 ? C24 C25 C13 68(2) . 3_655 ? C20 C25 C13 55(2) . 3_655 ? C17 C25 C13 76(3) 3_655 3_655 ? C15 C25 H25A 54.0 3_655 . ? C16 C25 H25A 73.6 3_655 . ? C14 C25 H25A 126.0 3_655 . ? C24 C25 H25A 120.0 . . ? C20 C25 H25A 120.0 . . ? C17 C25 H25A 114.3 3_655 . ? C13 C25 H25A 162.2 3_655 . ? O1 C18 C16 118.2(18) . . ? O1 C18 H18A 107.8 . . ? C16 C18 H18A 107.8 . . ? O1 C18 H18B 107.8 . . ? C16 C18 H18B 107.8 . . ? H18A C18 H18B 107.1 . . ? C18 O1 H1B 138.5 . . ? O1B C18B C16 105.0(16) . . ? O1B C18B H18C 110.8 . . ? C16 C18B H18C 110.8 . . ? O1B C18B H18D 110.8 . . ? C16 C18B H18D 110.8 . . ? H18C C18B H18D 108.8 . . ? C18B O1B H1BA 113.6 . . ? F12 P2 F11 167.5(9) . . ? F12 P2 F9 79.7(10) . . ? F11 P2 F9 90.2(4) . . ? F12 P2 F8B 86.3(11) . . ? F11 P2 F8B 97.8(8) . . ? F9 P2 F8B 142.8(6) . . ? F12 P2 F8 83.3(8) . . ? F11 P2 F8 89.5(7) . . ? F9 P2 F8 89.8(3) . . ? F8B P2 F8 54.2(5) . . ? F12 P2 F10 92.1(9) . . ? F11 P2 F10 95.3(8) . . ? F9 P2 F10 90.4(4) . . ? F8B P2 F10 124.6(6) . . ? F8 P2 F10 175.3(7) . . ? F12 P2 F10B 102.5(12) . . ? F11 P2 F10B 73.8(8) . . ? F9 P2 F10B 41.9(6) . . ? F8B P2 F10B 171.2(9) . . ? F8 P2 F10B 126.9(6) . . ? F10 P2 F10B 55.1(6) . . ? F12 P2 F7B 96.9(10) . . ? F11 P2 F7B 94.8(9) . . ? F9 P2 F7B 125.1(7) . . ? F8B P2 F7B 90.6(4) . . ? F8 P2 F7B 144.8(6) . . ? F10 P2 F7B 34.6(7) . . ? F10B P2 F7B 87.6(7) . . ? F12 P2 F9B 98.9(9) . . ? F11 P2 F9B 69.4(8) . . ? F9 P2 F9B 59.0(5) . . ? F8B P2 F9B 89.9(4) . . ? F8 P2 F9B 38.2(4) . . ? F10 P2 F9B 144.5(5) . . ? F10B P2 F9B 89.5(4) . . ? F7B P2 F9B 164.1(10) . . ? F12 P2 F7 95.0(10) . . ? F11 P2 F7 95.1(6) . . ? F9 P2 F7 174.6(6) . . ? F8B P2 F7 35.3(5) . . ? F8 P2 F7 89.1(4) . . ? F10 P2 F7 90.2(5) . . ? F10B P2 F7 141.1(8) . . ? F7B P2 F7 55.7(5) . . ? F9B P2 F7 122.0(6) . . ? F12 P2 F12B 16.2(15) . . ? F11 P2 F12B 174.5(13) . . ? F9 P2 F12B 89.7(13) . . ? F8B P2 F12B 85.6(16) . . ? F8 P2 F12B 96.0(13) . . ? F10 P2 F12B 79.3(13) . . ? F10B P2 F12B 102.6(16) . . ? F7B P2 F12B 80.8(12) . . ? F9B P2 F12B 115.1(12) . . ? F7 P2 F12B 85.2(13) . . ? F12 P2 F11B 168.7(11) . . ? F11 P2 F11B 23.4(7) . . ? F9 P2 F11B 111.2(8) . . ? F8B P2 F11B 86.4(11) . . ? F8 P2 F11B 99.4(9) . . ? F10 P2 F11B 84.9(9) . . ? F10B P2 F11B 84.7(11) . . ? F7B P2 F11B 74.5(10) . . ? F9B P2 F11B 89.7(5) . . ? F7 P2 F11B 74.1(9) . . ? F12B P2 F11B 153.9(11) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.308 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.058 data_mo_111228c2_0m _database_code_depnum_ccdc_archive 'CCDC 890902' #TrackingRef 'CPQT_NO2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H35 F24 N5 O7 P4' _chemical_formula_weight 1241.58 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 10.0819(18) _cell_length_b 10.9811(19) _cell_length_c 14.025(3) _cell_angle_alpha 68.984(5) _cell_angle_beta 76.417(5) _cell_angle_gamma 79.993(5) _cell_volume 1402.0(4) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.260 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9629 _exptl_absorpt_correction_T_max 0.9672 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8246 _diffrn_reflns_av_R_equivalents 0.0421 _diffrn_reflns_av_sigmaI/netI 0.1457 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 25.50 _reflns_number_total 6501 _reflns_number_gt 2497 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker apex II' _computing_cell_refinement 'Bruker apex II' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.7(3) _refine_ls_number_reflns 6501 _refine_ls_number_parameters 696 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.2429 _refine_ls_R_factor_gt 0.1188 _refine_ls_wR_factor_ref 0.3799 _refine_ls_wR_factor_gt 0.2914 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 2.198 _refine_ls_shift/su_mean 0.142 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 C7 C 0.114(2) 0.732(2) 0.3832(15) 0.070(6) Uani 1 1 d . . . H7A H 0.0184 0.7584 0.3762 0.084 Uiso 1 1 calc R . . H7B H 0.1521 0.8074 0.3826 0.084 Uiso 1 1 calc R . . C8 C 0.7331(18) -0.1093(19) 0.5355(12) 0.056(5) Uani 1 1 d . . . H8A H 0.8057 -0.1740 0.5201 0.067 Uiso 1 1 calc R . . H8B H 0.7651 -0.0726 0.5785 0.067 Uiso 1 1 calc R . . C9 C 0.5958(14) 0.0354(15) 0.4147(11) 0.040(4) Uani 1 1 d . . . C10 C 0.474(2) 0.1477(19) 0.2666(13) 0.062(5) Uani 1 1 d . . . H10 H 0.4292 0.0743 0.2811 0.075 Uiso 1 1 calc R . . C11 C 0.5731(17) 0.1495(17) 0.3252(12) 0.048(4) Uani 1 1 d . . . C12 C 0.247(2) 0.590(3) 0.5188(18) 0.090(7) Uani 1 1 d . . . H12 H 0.3210 0.6380 0.4814 0.108 Uiso 1 1 calc R . . C14 C 0.7259(16) -0.0069(17) 0.4399(14) 0.054(5) Uani 1 1 d . . . H14 H 0.8038 0.0302 0.3961 0.065 Uiso 1 1 calc R . . C15 C 0.3563(16) 0.566(2) 0.1607(12) 0.055(5) Uani 1 1 d . . . C18 C 0.285(3) -0.0547(18) 0.9922(14) 0.084(7) Uani 1 1 d . . . H18A H 0.2049 -0.1014 1.0308 0.101 Uiso 1 1 calc R . . H18B H 0.3296 -0.0400 1.0406 0.101 Uiso 1 1 calc R . . C19 C 0.2560(19) 0.4865(18) 0.6066(12) 0.049(5) Uani 1 1 d . . . H19 H 0.3407 0.4641 0.6272 0.058 Uiso 1 1 calc R . . C20 C 0.5998(16) -0.163(2) 0.8111(15) 0.071(7) Uani 1 1 d . . . H20 H 0.6925 -0.1518 0.7883 0.085 Uiso 1 1 calc R . . C21 C 0.4845(18) -0.0405(18) 0.4881(16) 0.068(6) Uani 1 1 d . . . H21 H 0.3957 -0.0143 0.4754 0.081 Uiso 1 1 calc R . . C22 C 0.451(3) 0.267(2) 0.1844(14) 0.087(7) Uani 1 1 d . . . H22 H 0.3951 0.2683 0.1398 0.104 Uiso 1 1 calc R . . C23 C 0.1784(18) 0.2998(19) 0.7551(14) 0.053(5) Uani 1 1 d . . . C24 C 0.318(2) 0.7177(15) 0.2547(14) 0.057(5) Uani 1 1 d . . . H24 H 0.3541 0.7716 0.2786 0.068 Uiso 1 1 calc R . . C25 C 0.117(2) 0.1835(18) 0.7734(14) 0.069(6) Uani 1 1 d . . . H25 H 0.0608 0.1815 0.7302 0.082 Uiso 1 1 calc R . . C26 C 0.159(2) 0.4165(17) 0.6638(15) 0.055(5) Uani 1 1 d . . . C27 C 0.1886(19) 0.6914(19) 0.2942(15) 0.059(5) Uani 1 1 d . . . C28 C 0.5556(19) -0.2384(17) 0.7785(12) 0.053(5) Uani 1 1 d . . . C29 C 0.4298(16) -0.2929(16) 0.8342(12) 0.042(4) Uani 1 1 d . . . C30 C 0.523(2) -0.0911(19) 0.8814(14) 0.060(5) Uani 1 1 d . . . H30 H 0.5562 -0.0272 0.8960 0.072 Uiso 1 1 calc R . . C31 C 0.3416(19) -0.2228(17) 0.9015(13) 0.049(4) Uani 1 1 d . . . H31 H 0.2511 -0.2415 0.9288 0.059 Uiso 1 1 calc R . . C32 C 0.3996(19) 0.672(2) 0.1836(15) 0.062(5) Uani 1 1 d . . . H32 H 0.4827 0.7057 0.1489 0.074 Uiso 1 1 calc R . . C33 C 0.6314(16) 0.2569(17) 0.2993(15) 0.053(5) Uani 1 1 d . . . H33 H 0.7031 0.2555 0.3311 0.063 Uiso 1 1 calc R . . C34 C 0.144(2) 0.073(2) 0.8575(19) 0.078(7) Uani 1 1 d . . . H34 H 0.0971 -0.0010 0.8784 0.094 Uiso 1 1 calc R . . C35 C 0.223(2) 0.553(2) 0.1972(17) 0.078(7) Uani 1 1 d . . . H35 H 0.1866 0.4965 0.1766 0.093 Uiso 1 1 calc R . . C36 C 0.136(2) 0.610(2) 0.2597(18) 0.085(7) Uani 1 1 d . . . H36 H 0.0440 0.5964 0.2791 0.103 Uiso 1 1 calc R . . C37 C 0.5900(18) 0.3747(19) 0.2252(13) 0.062(5) Uani 1 1 d . . . H37 H 0.6243 0.4520 0.2167 0.075 Uiso 1 1 calc R . . C39 C 0.5037(15) -0.1459(16) 0.5728(11) 0.042(4) Uani 1 1 d . . . H39 H 0.4316 -0.1952 0.6130 0.050 Uiso 1 1 calc R . . C40 C 0.0343(18) 0.4541(17) 0.6278(15) 0.058(5) Uani 1 1 d . . . H40 H -0.0379 0.4034 0.6644 0.070 Uiso 1 1 calc R . . C41 C 0.6473(15) -0.2799(16) 0.6908(12) 0.050(5) Uani 1 1 d . . . H41 H 0.7055 -0.3568 0.6969 0.060 Uiso 1 1 calc R . . C42 C 0.0124(18) 0.5575(18) 0.5448(15) 0.056(5) Uani 1 1 d . . . H42 H -0.0743 0.5837 0.5278 0.067 Uiso 1 1 calc R . . C43 C 0.389(3) -0.1346(18) 0.9233(14) 0.072(7) Uani 1 1 d . . . C44 C 0.2966(17) 0.1820(16) 0.8968(12) 0.044(4) Uani 1 1 d . . . H44 H 0.3543 0.1804 0.9403 0.053 Uiso 1 1 calc R . . C45 C 0.451(2) 0.494(2) 0.0987(14) 0.067(6) Uani 1 1 d . . . H45A H 0.4035 0.4738 0.0543 0.080 Uiso 1 1 calc R . . H45B H 0.5253 0.5455 0.0551 0.080 Uiso 1 1 calc R . . C46 C 0.266(2) 0.2955(19) 0.8178(14) 0.065(5) Uani 1 1 d . . . H46 H 0.3062 0.3707 0.8068 0.078 Uiso 1 1 calc R . . C55 C 0.700(3) 0.203(2) 0.617(3) 0.140(12) Uani 1 1 d . . . H55A H 0.6960 0.2703 0.6467 0.210 Uiso 1 1 calc R . . H55B H 0.7441 0.2330 0.5451 0.210 Uiso 1 1 calc R . . H55C H 0.7518 0.1254 0.6538 0.210 Uiso 1 1 calc R . . P1 P 0.6772(7) 0.3116(8) 0.8842(5) 0.097(2) Uani 1 1 d . . . P2 P 0.0708(6) 0.8660(7) 0.6618(5) 0.0799(19) Uani 1 1 d . . . P3 P 0.0831(7) 0.1372(7) 0.1940(5) 0.094(2) Uani 1 1 d . . . P4 P 0.6764(6) 0.5967(7) 0.4062(6) 0.090(2) Uani 1 1 d . . . F1 F 0.686(5) 0.177(2) 0.887(3) 0.29(2) Uani 1 1 d . . . F2 F 0.7155(19) 0.275(2) 0.9904(13) 0.188(10) Uani 1 1 d . . . F3 F 0.816(2) 0.295(3) 0.842(3) 0.266(18) Uani 1 1 d . . . F4 F 0.617(5) 0.436(3) 0.8949(18) 0.42(3) Uani 1 1 d . . . F5 F 0.735(5) 0.387(3) 0.796(3) 0.33(3) Uani 1 1 d . . . F6 F 0.589(2) 0.327(4) 0.8010(17) 0.232(14) Uani 1 1 d . . . F7 F 0.116(4) 0.794(3) 0.760(3) 0.37(3) Uani 1 1 d . . . F8 F 0.1968(18) 0.801(4) 0.609(3) 0.287(19) Uani 1 1 d . . . F9 F 0.039(3) 0.938(3) 0.5521(16) 0.216(12) Uani 1 1 d . . . F10 F 0.1637(16) 0.9735(16) 0.6383(13) 0.139(6) Uani 1 1 d . . . F11 F -0.048(2) 0.958(2) 0.697(3) 0.245(14) Uani 1 1 d . . . F12 F -0.0101(15) 0.7590(17) 0.6635(18) 0.160(8) Uani 1 1 d . . . F13 F 0.640(4) 0.583(2) 0.5223(11) 0.258(16) Uani 1 1 d . . . F14 F 0.572(3) 0.716(2) 0.385(2) 0.223(12) Uani 1 1 d . . . F15 F 0.694(3) 0.630(2) 0.2898(13) 0.199(10) Uani 1 1 d . . . F16 F 0.7995(18) 0.507(3) 0.412(2) 0.207(12) Uani 1 1 d . . . F17 F 0.7687(19) 0.7045(15) 0.3873(17) 0.157(7) Uani 1 1 d . . . F18 F 0.2282(13) 0.097(2) 0.1583(19) 0.177(9) Uani 1 1 d . . . F19 F -0.046(2) 0.228(4) 0.193(3) 0.36(2) Uani 1 1 d . . . F20 F 0.136(3) 0.259(2) 0.177(4) 0.33(3) Uani 1 1 d . . . F21 F 0.078(4) 0.187(3) 0.0839(14) 0.30(2) Uani 1 1 d . . . F22 F 0.066(3) 0.0009(18) 0.191(2) 0.227(13) Uani 1 1 d . . . F23 F 0.590(2) 0.494(3) 0.412(3) 0.270(18) Uani 1 1 d . . . F24 F 0.097(7) 0.075(3) 0.3040(19) 0.42(3) Uani 1 1 d . . . N1 N 0.5039(13) 0.3761(17) 0.1685(9) 0.049(4) Uani 1 1 d . . . N2 N 0.6261(14) -0.1770(13) 0.5970(11) 0.063(5) Uani 1 1 d . . . N3 N 0.2428(19) 0.0797(16) 0.9080(11) 0.068(5) Uani 1 1 d . . . N4 N 0.1204(14) 0.6217(14) 0.4873(10) 0.051(4) Uani 1 1 d . . . N5 N 0.3692(15) -0.3866(16) 0.8204(14) 0.070(4) Uani 1 1 d . . . O1 O 0.2908(14) -0.4569(14) 0.8930(11) 0.088(4) Uani 1 1 d . . . O2 O 0.3996(15) -0.4070(13) 0.7327(11) 0.091(4) Uani 1 1 d . . . O3 O 0.213(7) 0.296(3) 0.4328(19) 0.52(5) Uani 1 1 d . . . O4 O 0.516(4) 0.164(2) 0.6272(17) 0.249(18) Uani 1 1 d . . . H4 H 0.5088 0.1565 0.5725 0.374 Uiso 1 1 calc R . . O10 O 0.808(6) 0.613(4) 0.003(3) 0.42(4) Uani 1 1 d . . . O11 O 0.958(5) 0.849(8) 0.049(2) 0.47(5) Uani 1 1 d . . . O12 O 0.787(4) 0.933(3) 0.108(3) 0.251(16) 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 C7 0.073(13) 0.058(13) 0.068(12) -0.005(11) -0.005(11) -0.023(11) C8 0.049(11) 0.069(13) 0.039(9) -0.021(9) 0.026(8) -0.015(10) C9 0.029(8) 0.047(11) 0.031(8) 0.005(8) -0.004(7) -0.008(8) C10 0.088(14) 0.060(13) 0.033(9) -0.004(9) -0.006(10) -0.027(11) C11 0.051(10) 0.055(12) 0.032(9) -0.012(9) -0.004(8) -0.004(9) C12 0.078(15) 0.12(2) 0.091(17) -0.056(16) -0.009(13) -0.027(14) C14 0.027(9) 0.067(13) 0.057(11) -0.013(10) 0.001(8) -0.005(8) C15 0.032(9) 0.087(15) 0.034(9) -0.013(9) -0.009(7) 0.010(9) C18 0.140(19) 0.053(13) 0.039(10) 0.012(10) -0.043(12) 0.016(13) C19 0.059(11) 0.064(12) 0.020(8) -0.003(8) -0.022(8) -0.003(10) C20 0.025(9) 0.079(15) 0.064(12) 0.036(12) -0.032(9) 0.013(9) C21 0.036(9) 0.045(12) 0.106(16) -0.025(12) 0.018(9) -0.006(9) C22 0.16(2) 0.066(16) 0.033(11) -0.002(11) -0.014(12) -0.042(16) C23 0.045(11) 0.058(14) 0.051(11) -0.023(10) 0.014(9) -0.009(10) C24 0.102(16) 0.021(9) 0.054(11) -0.005(8) -0.032(11) -0.016(9) C25 0.096(15) 0.036(12) 0.045(10) 0.012(9) -0.023(10) 0.025(11) C26 0.083(15) 0.031(11) 0.054(11) -0.017(10) -0.029(11) 0.012(10) C27 0.048(11) 0.063(13) 0.076(13) -0.044(11) 0.010(9) -0.012(10) C28 0.065(12) 0.045(11) 0.035(9) 0.021(8) -0.042(9) -0.003(10) C29 0.035(8) 0.030(9) 0.041(9) 0.014(8) -0.011(7) -0.003(7) C30 0.081(14) 0.068(13) 0.045(10) -0.037(10) -0.016(10) 0.000(11) C31 0.065(11) 0.044(11) 0.042(10) -0.021(9) -0.005(8) -0.006(9) C32 0.056(11) 0.083(16) 0.054(11) -0.021(12) -0.022(10) -0.014(11) C33 0.034(9) 0.043(11) 0.089(13) -0.019(10) -0.020(9) -0.018(8) C34 0.055(12) 0.095(17) 0.117(18) -0.076(16) -0.029(12) 0.015(11) C35 0.047(12) 0.108(19) 0.089(15) -0.028(14) -0.030(12) -0.022(12) C36 0.055(12) 0.13(2) 0.107(17) -0.092(16) 0.019(11) -0.038(12) C37 0.062(11) 0.058(13) 0.042(10) 0.015(10) 0.001(9) -0.029(10) C39 0.032(8) 0.050(11) 0.027(8) 0.003(8) -0.006(6) 0.005(8) C40 0.047(10) 0.041(11) 0.077(13) -0.009(10) -0.015(10) 0.000(9) C41 0.041(9) 0.050(11) 0.042(9) -0.011(8) -0.012(7) 0.035(8) C42 0.042(10) 0.047(12) 0.067(12) -0.007(10) -0.012(9) 0.006(9) C43 0.14(2) 0.025(10) 0.036(10) 0.000(8) -0.015(12) 0.017(12) C44 0.065(11) 0.022(9) 0.053(10) -0.015(8) -0.025(9) 0.003(8) C45 0.080(13) 0.079(15) 0.044(10) -0.032(11) -0.007(9) 0.002(12) C46 0.103(16) 0.047(12) 0.058(12) -0.024(10) -0.026(12) -0.011(11) C55 0.14(2) 0.056(15) 0.23(3) -0.018(18) -0.07(2) -0.019(15) P1 0.087(5) 0.121(6) 0.071(4) -0.040(4) -0.007(4) 0.027(5) P2 0.052(3) 0.119(6) 0.077(4) -0.049(4) -0.008(3) 0.000(4) P3 0.105(5) 0.095(5) 0.076(5) -0.030(4) 0.001(4) -0.016(4) P4 0.067(4) 0.117(6) 0.115(6) -0.061(5) -0.042(4) -0.003(4) F1 0.50(5) 0.146(18) 0.31(3) -0.14(2) -0.24(4) 0.14(3) F2 0.166(15) 0.29(3) 0.115(13) -0.013(14) -0.068(11) -0.088(15) F3 0.130(17) 0.17(2) 0.38(4) -0.07(3) 0.15(2) -0.015(17) F4 0.71(7) 0.31(3) 0.141(18) -0.13(2) -0.15(3) 0.36(5) F5 0.32(4) 0.14(2) 0.30(3) 0.03(2) 0.23(3) -0.05(2) F6 0.170(18) 0.40(4) 0.117(15) -0.09(2) -0.045(14) 0.01(2) F7 0.46(5) 0.26(3) 0.35(4) 0.18(3) -0.36(4) -0.19(3) F8 0.081(11) 0.49(4) 0.45(4) -0.40(4) 0.065(18) -0.074(19) F9 0.23(2) 0.26(2) 0.151(16) 0.023(17) -0.062(16) -0.17(2) F10 0.132(13) 0.131(13) 0.165(14) -0.051(11) -0.006(11) -0.071(11) F11 0.155(17) 0.153(17) 0.41(4) -0.14(2) 0.02(2) 0.036(15) F12 0.097(11) 0.136(14) 0.29(2) -0.087(15) -0.108(13) 0.008(10) F13 0.54(5) 0.169(17) 0.055(9) -0.040(10) 0.045(15) -0.14(2) F14 0.22(2) 0.126(15) 0.34(4) -0.077(19) -0.13(2) 0.034(15) F15 0.32(3) 0.22(2) 0.089(11) -0.074(13) 0.014(14) -0.12(2) F16 0.096(12) 0.25(3) 0.34(3) -0.20(3) -0.071(15) 0.062(14) F17 0.163(16) 0.081(10) 0.227(19) -0.006(12) -0.089(14) -0.039(10) F18 0.058(8) 0.24(2) 0.32(3) -0.20(2) -0.035(11) 0.005(10) F19 0.115(16) 0.41(5) 0.42(5) -0.06(4) -0.02(2) 0.13(2) F20 0.20(2) 0.131(18) 0.76(8) -0.20(3) -0.23(4) -0.012(16) F21 0.44(5) 0.25(3) 0.077(13) -0.014(14) 0.049(18) 0.12(3) F22 0.31(3) 0.101(13) 0.36(3) -0.091(18) -0.20(3) -0.022(14) F23 0.137(16) 0.41(4) 0.45(4) -0.35(4) -0.05(2) -0.06(2) F24 0.97(11) 0.18(2) 0.119(17) 0.023(17) -0.15(3) -0.22(4) N1 0.038(8) 0.087(13) 0.025(7) -0.017(8) -0.003(6) -0.021(8) N2 0.056(9) 0.038(9) 0.060(9) 0.005(7) -0.010(8) 0.041(7) N3 0.092(12) 0.053(11) 0.045(9) -0.020(8) -0.006(9) 0.032(10) N4 0.057(9) 0.069(11) 0.038(8) -0.026(7) -0.018(7) -0.008(8) N5 0.049(9) 0.067(11) 0.084(11) -0.015(10) -0.022(8) 0.006(8) O1 0.086(9) 0.073(9) 0.091(10) 0.004(8) -0.012(8) -0.044(8) O2 0.121(11) 0.092(11) 0.067(9) -0.031(8) -0.023(8) -0.010(9) O3 1.23(14) 0.18(3) 0.091(16) -0.080(18) -0.23(4) 0.36(5) O4 0.46(5) 0.17(2) 0.109(15) -0.105(15) -0.09(2) 0.16(3) O10 0.68(9) 0.35(5) 0.26(4) 0.15(3) -0.34(5) -0.37(6) O11 0.36(6) 0.87(12) 0.12(2) 0.06(4) -0.08(3) -0.40(8) O12 0.22(3) 0.20(3) 0.22(3) 0.07(2) -0.07(2) -0.01(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 C7 C27 1.47(3) . ? C7 N4 1.54(2) . ? C8 N2 1.36(2) . ? C8 C14 1.41(2) . ? C9 C14 1.40(2) . ? C9 C11 1.45(2) . ? C9 C21 1.48(2) . ? C10 C22 1.43(3) . ? C10 C11 1.44(2) . ? C11 C33 1.30(2) . ? C12 N4 1.39(2) . ? C12 C19 1.35(3) . ? C15 C35 1.33(2) . ? C15 C32 1.46(3) . ? C15 C45 1.47(2) . ? C18 N3 1.59(2) . ? C18 C43 1.62(3) . ? C19 C26 1.28(2) . ? C20 C28 1.26(3) . ? C20 C30 1.48(3) . ? C21 C39 1.35(2) . ? C22 N1 1.32(2) . ? C23 C46 1.37(2) . ? C23 C25 1.43(3) . ? C23 C26 1.47(3) . ? C24 C27 1.33(2) . ? C24 C32 1.32(3) . ? C25 C34 1.39(3) . ? C26 C40 1.41(2) . ? C27 C36 1.38(3) . ? C28 C29 1.43(2) . ? C28 C41 1.52(2) . ? C29 N5 1.37(2) . ? C29 C31 1.47(2) . ? C30 C43 1.43(3) . ? C31 C43 1.30(3) . ? C33 C37 1.41(2) . ? C34 N3 1.38(2) . ? C35 C36 1.33(3) . ? C37 N1 1.30(2) . ? C39 N2 1.312(19) . ? C40 C42 1.33(2) . ? C41 N2 1.427(19) . ? C42 N4 1.33(2) . ? C44 N3 1.28(2) . ? C44 C46 1.38(2) . ? C45 N1 1.42(2) . ? C55 O4 1.94(4) . ? P1 F5 1.28(2) . ? P1 F3 1.40(2) . ? P1 F1 1.46(2) . ? P1 F4 1.44(2) . ? P1 F2 1.521(16) . ? P1 F6 1.57(2) . ? P2 F7 1.447(19) . ? P2 F11 1.539(19) . ? P2 F8 1.515(19) . ? P2 F12 1.533(17) . ? P2 F10 1.529(15) . ? P2 F9 1.54(2) . ? P3 F21 1.45(2) . ? P3 F20 1.441(19) . ? P3 F24 1.47(2) . ? P3 F18 1.475(14) . ? P3 F19 1.50(2) . ? P3 F22 1.553(17) . ? P4 F16 1.442(18) . ? P4 F23 1.51(2) . ? P4 F13 1.541(16) . ? P4 F15 1.512(18) . ? P4 F14 1.52(2) . ? P4 F17 1.543(16) . ? N5 O1 1.236(18) . ? N5 O2 1.286(19) . ? 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 C27 C7 N4 111.9(16) . . ? N2 C8 C14 124.4(16) . . ? C14 C9 C11 121.6(14) . . ? C14 C9 C21 115.0(14) . . ? C11 C9 C21 123.3(13) . . ? C22 C10 C11 115.0(19) . . ? C33 C11 C10 118.3(15) . . ? C33 C11 C9 123.0(16) . . ? C10 C11 C9 118.5(16) . . ? N4 C12 C19 117(2) . . ? C9 C14 C8 116.6(15) . . ? C35 C15 C32 111.7(19) . . ? C35 C15 C45 127(2) . . ? C32 C15 C45 121.5(17) . . ? N3 C18 C43 103.4(13) . . ? C26 C19 C12 126.2(18) . . ? C28 C20 C30 128.2(18) . . ? C39 C21 C9 124.0(16) . . ? N1 C22 C10 123(2) . . ? C46 C23 C25 118.5(18) . . ? C46 C23 C26 120.9(19) . . ? C25 C23 C26 120.3(18) . . ? C27 C24 C32 123.9(18) . . ? C23 C25 C34 118(2) . . ? C19 C26 C40 114.2(17) . . ? C19 C26 C23 123.5(17) . . ? C40 C26 C23 122(2) . . ? C36 C27 C24 118.0(17) . . ? C36 C27 C7 121.9(18) . . ? C24 C27 C7 119.4(18) . . ? C20 C28 C29 118.3(19) . . ? C20 C28 C41 118.1(19) . . ? C29 C28 C41 123.1(18) . . ? N5 C29 C28 128.8(17) . . ? N5 C29 C31 114.9(15) . . ? C28 C29 C31 115.2(17) . . ? C20 C30 C43 109.4(17) . . ? C43 C31 C29 120.7(19) . . ? C24 C32 C15 118.8(18) . . ? C11 C33 C37 122.6(16) . . ? N3 C34 C25 116(2) . . ? C15 C35 C36 128(2) . . ? C27 C36 C35 117.2(19) . . ? N1 C37 C33 120.4(19) . . ? N2 C39 C21 118.7(16) . . ? C42 C40 C26 124.5(18) . . ? N2 C41 C28 106.0(11) . . ? N4 C42 C40 117.0(16) . . ? C31 C43 C30 125.1(19) . . ? C31 C43 C18 118(2) . . ? C30 C43 C18 116(2) . . ? N3 C44 C46 117.6(16) . . ? N1 C45 C15 107.8(14) . . ? C23 C46 C44 121.6(19) . . ? F5 P1 F3 56.2(19) . . ? F5 P1 F1 112(2) . . ? F3 P1 F1 81(2) . . ? F5 P1 F4 82(2) . . ? F3 P1 F4 120(3) . . ? F1 P1 F4 159(3) . . ? F5 P1 F2 129(3) . . ? F3 P1 F2 88.6(19) . . ? F1 P1 F2 94.5(15) . . ? F4 P1 F2 87.9(15) . . ? F5 P1 F6 72(3) . . ? F3 P1 F6 110(2) . . ? F1 P1 F6 78.9(18) . . ? F4 P1 F6 91.6(19) . . ? F2 P1 F6 159.0(14) . . ? F7 P2 F11 100(3) . . ? F7 P2 F8 88(2) . . ? F11 P2 F8 168(2) . . ? F7 P2 F12 96.2(12) . . ? F11 P2 F12 99.7(12) . . ? F8 P2 F12 88.0(12) . . ? F7 P2 F10 91.3(12) . . ? F11 P2 F10 87.1(12) . . ? F8 P2 F10 83.9(13) . . ? F12 P2 F10 168.7(12) . . ? F7 P2 F9 174(2) . . ? F11 P2 F9 85.2(17) . . ? F8 P2 F9 86(2) . . ? F12 P2 F9 85.2(11) . . ? F10 P2 F9 86.4(10) . . ? F21 P3 F20 86(2) . . ? F21 P3 F24 174(2) . . ? F20 P3 F24 97(2) . . ? F21 P3 F18 84.2(16) . . ? F20 P3 F18 82.8(15) . . ? F24 P3 F18 92(3) . . ? F21 P3 F19 78.9(19) . . ? F20 P3 F19 79(2) . . ? F24 P3 F19 106(3) . . ? F18 P3 F19 155.9(19) . . ? F21 P3 F22 86.3(18) . . ? F20 P3 F22 163(2) . . ? F24 P3 F22 89.3(15) . . ? F18 P3 F22 81.3(13) . . ? F19 P3 F22 114(2) . . ? F16 P4 F23 93.1(15) . . ? F16 P4 F13 96.7(17) . . ? F23 P4 F13 97.1(16) . . ? F16 P4 F15 92.8(17) . . ? F23 P4 F15 84.6(15) . . ? F13 P4 F15 170.3(18) . . ? F16 P4 F14 165.7(17) . . ? F23 P4 F14 99.4(15) . . ? F13 P4 F14 88.7(18) . . ? F15 P4 F14 81.6(16) . . ? F16 P4 F17 86.5(13) . . ? F23 P4 F17 173.8(17) . . ? F13 P4 F17 89.1(12) . . ? F15 P4 F17 89.2(12) . . ? F14 P4 F17 80.3(12) . . ? C22 N1 C37 119.4(18) . . ? C22 N1 C45 117.7(16) . . ? C37 N1 C45 122.4(18) . . ? C39 N2 C8 120.8(14) . . ? C39 N2 C41 120.2(15) . . ? C8 N2 C41 119.0(14) . . ? C44 N3 C34 126.6(17) . . ? C44 N3 C18 118.9(18) . . ? C34 N3 C18 114(2) . . ? C42 N4 C12 121.2(16) . . ? C42 N4 C7 122.4(14) . . ? C12 N4 C7 116.4(17) . . ? O1 N5 O2 119.0(18) . . ? O1 N5 C29 121.0(17) . . ? O2 N5 C29 120.0(16) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.678 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.109