# Electronic Supplementary Material (ESI) for RSC Advances # 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_Compound-6A #TrackingRef 'COOMPOUND6A.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common CPWWSS _chemical_melting_point ? _chemical_absolute_configuration rm _chemical_formula_moiety 'C25 H22 N4 O2' _chemical_formula_sum 'C25 H22 N4 O2' _chemical_formula_weight 410.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M 'P 43' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+3/4' 'y, -x, z+1/4' _cell_length_a 19.7959(19) _cell_length_b 19.7959(19) _cell_length_c 11.155(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4371.4(11) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 999 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 26.00 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type PSI-SCAN _exptl_absorpt_correction_T_min 0.9839 _exptl_absorpt_correction_T_max 0.9903 _exptl_absorpt_process_details '(North et al., 1968)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area Detector' _diffrn_measurement_method 'Phi-Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24249 _diffrn_reflns_av_R_equivalents 0.0652 _diffrn_reflns_av_sigmaI/netI 0.0827 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 26.00 _reflns_number_total 8484 _reflns_number_gt 6571 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SMART 5.628 (Bruker, 2003)' _computing_data_reduction 'SAINT+ 6.45 (Bruker, 2003)' _computing_structure_solution Sir92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'diamond 3.1d' _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^)+(0.0541P)^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 0.2(11) _refine_ls_number_reflns 8484 _refine_ls_number_parameters 559 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0745 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.1237 _refine_ls_wR_factor_gt 0.1149 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 O1A O 0.53214(9) 1.16865(9) 0.36501(17) 0.0292(4) Uani 1 1 d . . . O2A O 0.55445(10) 0.94860(10) 0.08965(19) 0.0386(5) Uani 1 1 d . . . C17 C 0.80122(16) 1.39670(15) -0.7763(3) 0.0350(7) Uani 1 1 d . . . H17A H 0.8197 1.4417 -0.7665 0.042 Uiso 1 1 calc R . . H17B H 0.8304 1.3725 -0.8313 0.042 Uiso 1 1 calc R . . C17A C 0.46936(14) 1.17347(14) 0.1520(3) 0.0300(7) Uani 1 1 d . . . H17C H 0.4380 1.1821 0.2170 0.036 Uiso 1 1 calc R . . H17D H 0.4431 1.1588 0.0833 0.036 Uiso 1 1 calc R . . C18A C 0.50277(15) 1.23694(16) 0.1212(3) 0.0376(7) Uani 1 1 d . . . C18 C 0.73477(19) 1.40252(19) -0.8304(3) 0.0487(9) Uani 1 1 d . . . C19A C 0.52521(19) 1.2900(2) 0.0954(4) 0.0629(11) Uani 1 1 d . . . H19A H 0.5430 1.3320 0.0751 0.076 Uiso 1 1 calc R . . C19 C 0.6831(2) 1.4125(2) -0.8793(4) 0.0781(14) Uani 1 1 d . . . H19 H 0.6422 1.4203 -0.9179 0.094 Uiso 1 1 calc R . . O1 O 0.81695(10) 1.26085(10) -0.74903(17) 0.0319(5) Uani 1 1 d . . . O2 O 0.84886(11) 1.41407(10) -0.36448(18) 0.0383(5) Uani 1 1 d . . . N1A N 0.51398(11) 1.11826(11) 0.1876(2) 0.0269(5) Uani 1 1 d . . . C2A C 0.54065(13) 1.11961(14) 0.2981(2) 0.0257(6) Uani 1 1 d . . . N4 N 0.83690(11) 1.30926(11) -0.4399(2) 0.0285(5) Uani 1 1 d . . . H4 H 0.8492 1.2924 -0.3723 0.034 Uiso 1 1 calc R . . N4A N 0.57425(12) 1.00016(12) 0.2670(2) 0.0300(5) Uani 1 1 d . . . H4A H 0.5855 0.9620 0.2978 0.036 Uiso 1 1 calc R . . N1 N 0.80333(12) 1.36246(11) -0.6600(2) 0.0272(5) Uani 1 1 d . . . C15B C 0.73946(14) 0.94077(14) 0.5413(2) 0.0277(6) Uani 1 1 d . . . C16' C 0.83126(13) 1.10748(14) -0.4108(3) 0.0280(6) Uani 1 1 d . . . C16B C 0.68769(13) 0.98904(13) 0.5347(2) 0.0243(6) Uani 1 1 d . . . C10A C 0.64811(14) 1.11147(14) 0.0450(2) 0.0286(6) Uani 1 1 d . . . C3 C 0.82585(13) 1.26187(14) -0.5377(2) 0.0264(6) Uani 1 1 d . . . H3 H 0.8678 1.2361 -0.5462 0.032 Uiso 1 1 calc R . . C2 C 0.81402(13) 1.29611(14) -0.6567(3) 0.0279(6) Uani 1 1 d . . . C10B C 0.69465(13) 1.02311(14) 0.4211(2) 0.0257(6) Uani 1 1 d . . . N8' N 0.77942(13) 1.10915(13) -0.2320(2) 0.0389(6) Uani 1 1 d . . . H8' H 0.7677 1.0994 -0.1598 0.047 Uiso 1 1 calc R . . N8A N 0.73404(12) 1.17484(12) 0.1145(2) 0.0335(6) Uani 1 1 d . . . H8A H 0.7558 1.2091 0.1421 0.040 Uiso 1 1 calc R . . C16 C 0.65943(14) 1.33643(15) -0.3916(3) 0.0346(7) Uani 1 1 d . . . C10' C 0.78504(14) 1.16360(14) -0.4083(3) 0.0295(6) Uani 1 1 d . . . C3A C 0.57853(14) 1.05952(13) 0.3449(3) 0.0263(6) Uani 1 1 d . . . H3A H 0.5575 1.0471 0.4212 0.032 Uiso 1 1 calc R . . C11A C 0.72328(15) 1.00284(15) 0.0212(2) 0.0312(7) Uani 1 1 d . . . H11A H 0.6896 0.9740 -0.0062 0.037 Uiso 1 1 calc R . . C9B C 0.74893(14) 0.99530(14) 0.3666(3) 0.0303(6) Uani 1 1 d . . . H9B H 0.7657 1.0086 0.2924 0.036 Uiso 1 1 calc R . . C6A C 0.52967(14) 1.06550(14) 0.0981(3) 0.0272(6) Uani 1 1 d . . . H6A H 0.4871 1.0552 0.0571 0.033 Uiso 1 1 calc R . . C13' C 0.90281(16) 0.99041(15) -0.3628(3) 0.0384(8) Uani 1 1 d . . . H13' H 0.9261 0.9503 -0.3495 0.046 Uiso 1 1 calc R . . C12A C 0.78844(15) 0.97955(15) 0.0340(2) 0.0321(7) Uani 1 1 d . . . H12A H 0.7984 0.9349 0.0154 0.038 Uiso 1 1 calc R . . C7A C 0.57913(14) 1.09113(14) 0.0004(3) 0.0294(6) Uani 1 1 d . . . H7A1 H 0.5846 1.0559 -0.0591 0.035 Uiso 1 1 calc R . . H7A2 H 0.5588 1.1297 -0.0393 0.035 Uiso 1 1 calc R . . C14' C 0.86107(15) 1.01434(14) -0.2748(3) 0.0358(7) Uani 1 1 d . . . H14' H 0.8564 0.9921 -0.2018 0.043 Uiso 1 1 calc R . . C16A C 0.70784(14) 1.07005(15) 0.0494(2) 0.0298(7) Uani 1 1 d . . . C15' C 0.82583(14) 1.07371(14) -0.2997(3) 0.0300(7) Uani 1 1 d . . . N8B N 0.77618(12) 0.94442(12) 0.4362(2) 0.0320(6) Uani 1 1 d . . . H8B H 0.8101 0.9194 0.4174 0.038 Uiso 1 1 calc R . . C11B C 0.64321(14) 0.99588(14) 0.6329(3) 0.0287(6) Uani 1 1 d . . . H11B H 0.6090 1.0281 0.6321 0.034 Uiso 1 1 calc R . . C11' C 0.87553(15) 1.08184(14) -0.4971(3) 0.0328(7) Uani 1 1 d . . . H11' H 0.8805 1.1035 -0.5705 0.039 Uiso 1 1 calc R . . C7' C 0.77029(14) 1.21025(14) -0.5117(3) 0.0294(6) Uani 1 1 d . . . H7'1 H 0.7287 1.2343 -0.4950 0.035 Uiso 1 1 calc R . . H7'2 H 0.7630 1.1832 -0.5831 0.035 Uiso 1 1 calc R . . C5A C 0.55430(14) 0.99989(14) 0.1518(3) 0.0286(6) Uani 1 1 d . . . C14B C 0.74747(15) 0.89754(15) 0.6389(3) 0.0343(7) Uani 1 1 d . . . H14B H 0.7809 0.8646 0.6402 0.041 Uiso 1 1 calc R . . C7 C 0.72152(14) 1.42469(14) -0.5286(3) 0.0332(7) Uani 1 1 d . . . H7A H 0.7202 1.4548 -0.4600 0.040 Uiso 1 1 calc R . . H7B H 0.7042 1.4494 -0.5971 0.040 Uiso 1 1 calc R . . C13B C 0.70327(15) 0.90601(15) 0.7336(3) 0.0365(7) Uani 1 1 d . . . H13B H 0.7081 0.8792 0.8015 0.044 Uiso 1 1 calc R . . C5 C 0.82991(14) 1.37581(14) -0.4449(3) 0.0286(6) Uani 1 1 d . . . C15 C 0.61488(14) 1.28265(16) -0.4126(3) 0.0373(7) Uani 1 1 d . . . C15A C 0.76135(14) 1.11201(15) 0.0926(3) 0.0309(7) Uani 1 1 d . . . C14A C 0.82711(15) 1.08921(16) 0.1053(3) 0.0344(7) Uani 1 1 d . . . H14A H 0.8611 1.1175 0.1333 0.041 Uiso 1 1 calc R . . C12B C 0.65175(16) 0.95383(16) 0.7297(3) 0.0362(7) Uani 1 1 d . . . H12B H 0.6223 0.9574 0.7944 0.043 Uiso 1 1 calc R . . C10 C 0.67568(14) 1.36613(15) -0.5045(3) 0.0320(7) Uani 1 1 d . . . C7B C 0.65210(13) 1.07972(14) 0.3731(2) 0.0278(6) Uani 1 1 d . . . H7B1 H 0.6729 1.0969 0.3005 0.033 Uiso 1 1 calc R . . H7B2 H 0.6517 1.1161 0.4313 0.033 Uiso 1 1 calc R . . C9 C 0.64023(15) 1.32959(15) -0.5886(3) 0.0369(7) Uani 1 1 d . . . H9 H 0.6410 1.3379 -0.6707 0.044 Uiso 1 1 calc R . . C9' C 0.75471(15) 1.16245(16) -0.2980(3) 0.0367(7) Uani 1 1 d . . . H9' H 0.7223 1.1931 -0.2717 0.044 Uiso 1 1 calc R . . C12' C 0.91171(16) 1.02403(15) -0.4720(3) 0.0376(7) Uani 1 1 d . . . H12' H 0.9422 1.0073 -0.5281 0.045 Uiso 1 1 calc R . . C13A C 0.84032(15) 1.02291(17) 0.0750(3) 0.0376(7) Uani 1 1 d . . . H13A H 0.8842 1.0064 0.0817 0.045 Uiso 1 1 calc R . . C13 C 0.60869(17) 1.25736(19) -0.2051(4) 0.0538(10) Uani 1 1 d . . . H13 H 0.5913 1.2322 -0.1419 0.065 Uiso 1 1 calc R . . C6 C 0.79657(14) 1.40544(13) -0.5536(3) 0.0283(6) Uani 1 1 d . . . H6 H 0.8204 1.4477 -0.5715 0.034 Uiso 1 1 calc R . . C9A C 0.66691(15) 1.17424(15) 0.0856(3) 0.0328(7) Uani 1 1 d . . . H9A H 0.6381 1.2111 0.0925 0.039 Uiso 1 1 calc R . . N8 N 0.60356(12) 1.27930(13) -0.5346(2) 0.0402(7) Uani 1 1 d . . . H8 H 0.5780 1.2506 -0.5705 0.048 Uiso 1 1 calc R . . C11 C 0.67905(16) 1.35024(18) -0.2718(3) 0.0438(8) Uani 1 1 d . . . H11 H 0.7085 1.3855 -0.2545 0.053 Uiso 1 1 calc R . . C14 C 0.58975(15) 1.24175(18) -0.3215(4) 0.0487(9) Uani 1 1 d . . . H14 H 0.5614 1.2055 -0.3380 0.058 Uiso 1 1 calc R . . C12 C 0.65325(18) 1.3099(2) -0.1811(3) 0.0554(10) Uani 1 1 d . . . H12 H 0.6661 1.3182 -0.1023 0.066 Uiso 1 1 calc R . . 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 O1A 0.0302(11) 0.0338(11) 0.0235(11) -0.0032(9) 0.0016(8) 0.0012(8) O2A 0.0485(13) 0.0344(12) 0.0328(12) -0.0061(10) -0.0027(10) -0.0024(9) C17 0.0449(18) 0.0367(17) 0.0236(16) 0.0050(13) 0.0036(14) 0.0002(14) C17A 0.0322(16) 0.0372(16) 0.0206(15) 0.0025(12) 0.0005(12) 0.0017(13) C18A 0.0369(17) 0.0381(18) 0.0379(19) 0.0032(15) 0.0039(14) 0.0051(14) C18 0.055(2) 0.059(2) 0.0314(19) 0.0131(16) -0.0038(17) -0.0157(18) C19A 0.059(2) 0.048(2) 0.082(3) 0.020(2) 0.009(2) -0.0033(18) C19 0.070(3) 0.103(3) 0.062(3) 0.036(3) -0.024(2) -0.033(3) O1 0.0406(12) 0.0331(11) 0.0219(11) -0.0037(9) 0.0020(9) -0.0013(9) O2 0.0487(13) 0.0378(12) 0.0284(12) -0.0097(10) -0.0012(10) -0.0080(10) N1A 0.0324(13) 0.0309(13) 0.0173(12) -0.0012(10) -0.0024(10) 0.0005(10) C2A 0.0234(14) 0.0323(16) 0.0214(15) 0.0003(12) 0.0023(12) -0.0072(12) N4 0.0363(13) 0.0296(13) 0.0197(13) -0.0006(10) -0.0025(10) -0.0009(11) N4A 0.0362(13) 0.0272(13) 0.0265(14) 0.0004(10) -0.0060(11) 0.0003(10) N1 0.0371(13) 0.0269(12) 0.0177(12) 0.0018(10) 0.0025(10) -0.0005(10) C15B 0.0312(15) 0.0297(15) 0.0221(15) -0.0028(12) -0.0044(12) -0.0039(12) C16' 0.0293(15) 0.0318(15) 0.0230(15) 0.0010(12) -0.0005(12) -0.0117(12) C16B 0.0260(14) 0.0289(15) 0.0179(14) -0.0005(11) -0.0034(11) -0.0064(12) C10A 0.0332(16) 0.0343(16) 0.0183(15) 0.0019(12) 0.0011(12) -0.0082(13) C3 0.0291(15) 0.0274(15) 0.0226(15) -0.0018(12) -0.0011(12) 0.0014(12) C2 0.0261(15) 0.0342(16) 0.0234(15) -0.0027(13) 0.0034(12) -0.0051(12) C10B 0.0232(14) 0.0333(16) 0.0207(15) -0.0041(12) -0.0047(11) -0.0038(12) N8' 0.0477(16) 0.0452(16) 0.0239(14) 0.0070(12) 0.0037(12) -0.0098(13) N8A 0.0342(14) 0.0380(14) 0.0281(14) -0.0045(11) 0.0006(11) -0.0119(11) C16 0.0254(15) 0.0427(18) 0.0356(19) -0.0057(15) 0.0073(13) -0.0025(13) C10' 0.0333(16) 0.0300(15) 0.0253(16) 0.0022(12) 0.0034(13) -0.0064(12) C3A 0.0318(15) 0.0276(14) 0.0196(14) -0.0007(12) -0.0010(12) -0.0030(12) C11A 0.0375(17) 0.0388(17) 0.0174(15) -0.0010(13) 0.0043(12) -0.0078(13) C9B 0.0292(15) 0.0399(17) 0.0219(16) 0.0036(13) -0.0021(12) -0.0024(12) C6A 0.0314(15) 0.0289(15) 0.0213(15) -0.0057(12) -0.0032(12) -0.0035(12) C13' 0.0477(19) 0.0302(16) 0.0373(19) 0.0022(14) -0.0141(15) 0.0014(14) C12A 0.0405(18) 0.0357(16) 0.0201(15) 0.0017(13) 0.0093(13) 0.0023(14) C7A 0.0354(16) 0.0304(15) 0.0225(15) -0.0017(12) 0.0000(13) -0.0006(12) C14' 0.0414(18) 0.0338(17) 0.0322(18) 0.0070(14) -0.0091(14) -0.0097(14) C16A 0.0365(16) 0.0382(17) 0.0147(14) 0.0037(12) 0.0050(12) -0.0075(13) C15' 0.0335(16) 0.0310(16) 0.0255(16) -0.0007(13) -0.0041(13) -0.0090(13) N8B 0.0292(13) 0.0392(14) 0.0275(14) -0.0020(11) -0.0005(11) 0.0070(11) C11B 0.0306(16) 0.0314(16) 0.0240(15) -0.0032(12) -0.0003(12) -0.0026(12) C11' 0.0424(17) 0.0329(16) 0.0233(16) -0.0039(13) -0.0010(13) -0.0027(13) C7' 0.0346(16) 0.0257(15) 0.0279(16) 0.0025(12) -0.0014(13) -0.0020(12) C5A 0.0314(16) 0.0279(15) 0.0264(16) -0.0025(12) 0.0020(12) -0.0057(12) C14B 0.0382(17) 0.0325(16) 0.0321(17) 0.0033(13) -0.0109(14) -0.0028(13) C7 0.0347(16) 0.0303(16) 0.0345(18) -0.0079(13) -0.0007(14) 0.0009(13) C13B 0.0436(19) 0.0440(19) 0.0218(16) 0.0079(14) -0.0094(14) -0.0096(15) C5 0.0291(15) 0.0295(16) 0.0271(16) -0.0034(13) 0.0070(12) -0.0050(12) C15 0.0298(16) 0.0411(18) 0.0409(19) -0.0074(15) 0.0081(14) -0.0017(13) C15A 0.0349(16) 0.0393(17) 0.0185(15) 0.0019(13) 0.0019(12) -0.0080(13) C14A 0.0337(16) 0.0473(19) 0.0222(16) 0.0019(14) 0.0033(13) -0.0091(14) C12B 0.0398(18) 0.0486(19) 0.0200(16) 0.0007(14) 0.0000(13) -0.0126(15) C10 0.0313(16) 0.0320(16) 0.0327(17) -0.0094(13) 0.0034(13) 0.0003(13) C7B 0.0303(15) 0.0334(15) 0.0196(15) 0.0033(12) 0.0003(12) -0.0078(12) C9 0.0338(17) 0.0383(18) 0.0385(19) -0.0047(14) 0.0007(14) -0.0011(14) C9' 0.0349(17) 0.0406(18) 0.0346(18) -0.0020(15) 0.0065(14) 0.0011(13) C12' 0.0452(19) 0.0341(17) 0.0336(18) -0.0031(14) -0.0004(15) 0.0042(14) C13A 0.0336(17) 0.056(2) 0.0233(16) 0.0074(15) 0.0042(13) 0.0010(15) C13 0.044(2) 0.062(2) 0.055(3) 0.014(2) 0.0255(19) 0.0030(18) C6 0.0360(16) 0.0222(14) 0.0269(16) -0.0031(12) 0.0044(12) -0.0030(12) C9A 0.0354(17) 0.0396(17) 0.0235(15) 0.0016(13) 0.0044(13) -0.0005(13) N8 0.0294(14) 0.0433(16) 0.0480(18) -0.0141(13) 0.0011(12) -0.0095(12) C11 0.0412(18) 0.055(2) 0.0349(19) -0.0129(16) 0.0090(15) -0.0100(15) C14 0.0259(17) 0.050(2) 0.070(3) -0.0002(19) 0.0188(17) -0.0045(14) C12 0.047(2) 0.079(3) 0.039(2) -0.0005(19) 0.0190(17) -0.005(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 O1A C2A 1.236(3) . ? O2A C5A 1.229(3) . ? C17 C18 1.452(5) . ? C17 N1 1.464(4) . ? C17A N1A 1.460(4) . ? C17A C18A 1.461(4) . ? C18A C19A 1.177(5) . ? C18 C19 1.177(5) . ? O1 C2 1.246(3) . ? O2 C5 1.232(3) . ? N1A C2A 1.341(3) . ? N1A C6A 1.478(3) . ? C2A C3A 1.500(4) . ? N4 C5 1.326(3) . ? N4 C3 1.455(3) . ? N4A C5A 1.345(4) . ? N4A C3A 1.463(3) . ? N1 C2 1.331(3) . ? N1 C6 1.466(3) . ? C15B N8B 1.381(4) . ? C15B C14B 1.394(4) . ? C15B C16B 1.403(4) . ? C16' C11' 1.397(4) . ? C16' C15' 1.413(4) . ? C16' C10' 1.440(4) . ? C16B C11B 1.412(4) . ? C16B C10B 1.442(4) . ? C10A C9A 1.374(4) . ? C10A C16A 1.440(4) . ? C10A C7A 1.508(4) . ? C3 C2 1.509(4) . ? C3 C7' 1.529(4) . ? C10B C9B 1.352(4) . ? C10B C7B 1.501(4) . ? N8' C9' 1.376(4) . ? N8' C15' 1.380(4) . ? N8A C9A 1.367(4) . ? N8A C15A 1.378(4) . ? C16 C15 1.402(4) . ? C16 C11 1.418(5) . ? C16 C10 1.426(5) . ? C10' C9' 1.369(4) . ? C10' C7' 1.505(4) . ? C3A C7B 1.543(4) . ? C11A C12A 1.377(4) . ? C11A C16A 1.401(4) . ? C9B N8B 1.381(4) . ? C6A C5A 1.511(4) . ? C6A C7A 1.550(4) . ? C13' C14' 1.368(4) . ? C13' C12' 1.400(4) . ? C12A C13A 1.415(4) . ? C14' C15' 1.395(4) . ? C16A C15A 1.430(4) . ? C11B C12B 1.373(4) . ? C11' C12' 1.379(4) . ? C14B C13B 1.382(4) . ? C7 C10 1.496(4) . ? C7 C6 1.559(4) . ? C13B C12B 1.392(4) . ? C5 C6 1.501(4) . ? C15 N8 1.381(4) . ? C15 C14 1.391(5) . ? C15A C14A 1.385(4) . ? C14A C13A 1.381(4) . ? C10 C9 1.377(4) . ? C9 N8 1.372(4) . ? C13 C14 1.386(5) . ? C13 C12 1.390(5) . ? C11 C12 1.386(5) . ? 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 C18 C17 N1 115.5(3) . . ? N1A C17A C18A 115.7(2) . . ? C19A C18A C17A 175.3(3) . . ? C19 C18 C17 173.9(4) . . ? C2A N1A C17A 118.3(2) . . ? C2A N1A C6A 123.5(2) . . ? C17A N1A C6A 118.2(2) . . ? O1A C2A N1A 121.1(2) . . ? O1A C2A C3A 118.7(2) . . ? N1A C2A C3A 120.1(2) . . ? C5 N4 C3 126.4(2) . . ? C5A N4A C3A 126.0(2) . . ? C2 N1 C17 119.1(2) . . ? C2 N1 C6 124.4(2) . . ? C17 N1 C6 116.5(2) . . ? N8B C15B C14B 129.4(3) . . ? N8B C15B C16B 107.7(2) . . ? C14B C15B C16B 122.8(3) . . ? C11' C16' C15' 118.7(3) . . ? C11' C16' C10' 133.8(3) . . ? C15' C16' C10' 107.4(2) . . ? C15B C16B C11B 118.7(2) . . ? C15B C16B C10B 107.1(2) . . ? C11B C16B C10B 134.1(3) . . ? C9A C10A C16A 106.3(2) . . ? C9A C10A C7A 126.5(3) . . ? C16A C10A C7A 127.1(2) . . ? N4 C3 C2 113.1(2) . . ? N4 C3 C7' 113.4(2) . . ? C2 C3 C7' 110.8(2) . . ? O1 C2 N1 122.5(3) . . ? O1 C2 C3 117.9(2) . . ? N1 C2 C3 119.5(2) . . ? C9B C10B C16B 106.3(2) . . ? C9B C10B C7B 126.1(2) . . ? C16B C10B C7B 127.5(2) . . ? C9' N8' C15' 109.5(2) . . ? C9A N8A C15A 109.4(2) . . ? C15 C16 C11 118.4(3) . . ? C15 C16 C10 107.9(3) . . ? C11 C16 C10 133.7(3) . . ? C9' C10' C16' 106.5(3) . . ? C9' C10' C7' 127.8(3) . . ? C16' C10' C7' 125.6(3) . . ? N4A C3A C2A 113.7(2) . . ? N4A C3A C7B 112.6(2) . . ? C2A C3A C7B 109.7(2) . . ? C12A C11A C16A 119.9(3) . . ? C10B C9B N8B 110.8(2) . . ? N1A C6A C5A 114.1(2) . . ? N1A C6A C7A 112.1(2) . . ? C5A C6A C7A 110.9(2) . . ? C14' C13' C12' 122.4(3) . . ? C11A C12A C13A 120.7(3) . . ? C10A C7A C6A 115.3(2) . . ? C13' C14' C15' 116.8(3) . . ? C11A C16A C15A 117.8(3) . . ? C11A C16A C10A 135.4(3) . . ? C15A C16A C10A 106.8(3) . . ? N8' C15' C14' 130.7(3) . . ? N8' C15' C16' 106.8(2) . . ? C14' C15' C16' 122.4(3) . . ? C9B N8B C15B 108.0(2) . . ? C12B C11B C16B 118.3(3) . . ? C12' C11' C16' 119.2(3) . . ? C10' C7' C3 114.6(2) . . ? O2A C5A N4A 122.8(3) . . ? O2A C5A C6A 119.2(3) . . ? N4A C5A C6A 118.0(2) . . ? C13B C14B C15B 116.8(3) . . ? C10 C7 C6 114.9(2) . . ? C14B C13B C12B 121.5(3) . . ? O2 C5 N4 123.3(3) . . ? O2 C5 C6 118.8(2) . . ? N4 C5 C6 117.9(2) . . ? N8 C15 C14 129.3(3) . . ? N8 C15 C16 107.6(3) . . ? C14 C15 C16 123.0(3) . . ? N8A C15A C14A 130.1(3) . . ? N8A C15A C16A 107.1(2) . . ? C14A C15A C16A 122.8(3) . . ? C13A C14A C15A 117.6(3) . . ? C11B C12B C13B 121.8(3) . . ? C9 C10 C16 105.7(3) . . ? C9 C10 C7 126.4(3) . . ? C16 C10 C7 127.9(3) . . ? C10B C7B C3A 114.1(2) . . ? N8 C9 C10 110.6(3) . . ? C10' C9' N8' 109.7(3) . . ? C11' C12' C13' 120.4(3) . . ? C14A C13A C12A 121.2(3) . . ? C14 C13 C12 121.3(3) . . ? N1 C6 C5 112.8(2) . . ? N1 C6 C7 112.0(2) . . ? C5 C6 C7 111.7(2) . . ? N8A C9A C10A 110.4(3) . . ? C9 N8 C15 108.2(2) . . ? C12 C11 C16 118.4(3) . . ? C13 C14 C15 117.2(3) . . ? C11 C12 C13 121.6(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1A C17A C18A C19A -176(4) . . . . ? N1 C17 C18 C19 152(4) . . . . ? C18A C17A N1A C2A 76.5(3) . . . . ? C18A C17A N1A C6A -100.8(3) . . . . ? C17A N1A C2A O1A -5.5(4) . . . . ? C6A N1A C2A O1A 171.7(2) . . . . ? C17A N1A C2A C3A 171.3(2) . . . . ? C6A N1A C2A C3A -11.5(4) . . . . ? C18 C17 N1 C2 91.8(3) . . . . ? C18 C17 N1 C6 -91.1(3) . . . . ? N8B C15B C16B C11B -179.3(2) . . . . ? C14B C15B C16B C11B 2.4(4) . . . . ? N8B C15B C16B C10B -0.6(3) . . . . ? C14B C15B C16B C10B -179.0(2) . . . . ? C5 N4 C3 C2 8.0(4) . . . . ? C5 N4 C3 C7' -119.3(3) . . . . ? C17 N1 C2 O1 -5.9(4) . . . . ? C6 N1 C2 O1 177.2(2) . . . . ? C17 N1 C2 C3 171.6(2) . . . . ? C6 N1 C2 C3 -5.2(4) . . . . ? N4 C3 C2 O1 166.5(2) . . . . ? C7' C3 C2 O1 -64.9(3) . . . . ? N4 C3 C2 N1 -11.1(3) . . . . ? C7' C3 C2 N1 117.5(3) . . . . ? C15B C16B C10B C9B -0.6(3) . . . . ? C11B C16B C10B C9B 177.7(3) . . . . ? C15B C16B C10B C7B -178.8(2) . . . . ? C11B C16B C10B C7B -0.4(5) . . . . ? C11' C16' C10' C9' 179.2(3) . . . . ? C15' C16' C10' C9' 0.8(3) . . . . ? C11' C16' C10' C7' 3.4(5) . . . . ? C15' C16' C10' C7' -175.0(3) . . . . ? C5A N4A C3A C2A 16.2(4) . . . . ? C5A N4A C3A C7B -109.4(3) . . . . ? O1A C2A C3A N4A 168.8(2) . . . . ? N1A C2A C3A N4A -8.0(4) . . . . ? O1A C2A C3A C7B -64.1(3) . . . . ? N1A C2A C3A C7B 119.0(3) . . . . ? C16B C10B C9B N8B 1.6(3) . . . . ? C7B C10B C9B N8B 179.9(2) . . . . ? C2A N1A C6A C5A 23.3(4) . . . . ? C17A N1A C6A C5A -159.5(2) . . . . ? C2A N1A C6A C7A -103.7(3) . . . . ? C17A N1A C6A C7A 73.5(3) . . . . ? C16A C11A C12A C13A -0.3(4) . . . . ? C9A C10A C7A C6A -88.4(3) . . . . ? C16A C10A C7A C6A 94.0(3) . . . . ? N1A C6A C7A C10A 62.9(3) . . . . ? C5A C6A C7A C10A -65.8(3) . . . . ? C12' C13' C14' C15' 1.5(4) . . . . ? C12A C11A C16A C15A -0.8(4) . . . . ? C12A C11A C16A C10A 178.3(3) . . . . ? C9A C10A C16A C11A -179.9(3) . . . . ? C7A C10A C16A C11A -1.9(5) . . . . ? C9A C10A C16A C15A -0.8(3) . . . . ? C7A C10A C16A C15A 177.2(3) . . . . ? C9' N8' C15' C14' -175.8(3) . . . . ? C9' N8' C15' C16' 1.5(3) . . . . ? C13' C14' C15' N8' 178.2(3) . . . . ? C13' C14' C15' C16' 1.3(4) . . . . ? C11' C16' C15' N8' 179.9(3) . . . . ? C10' C16' C15' N8' -1.4(3) . . . . ? C11' C16' C15' C14' -2.5(4) . . . . ? C10' C16' C15' C14' 176.2(3) . . . . ? C10B C9B N8B C15B -2.0(3) . . . . ? C14B C15B N8B C9B 179.8(3) . . . . ? C16B C15B N8B C9B 1.6(3) . . . . ? C15B C16B C11B C12B -1.4(4) . . . . ? C10B C16B C11B C12B -179.6(3) . . . . ? C15' C16' C11' C12' 1.0(4) . . . . ? C10' C16' C11' C12' -177.3(3) . . . . ? C9' C10' C7' C3 109.7(3) . . . . ? C16' C10' C7' C3 -75.4(3) . . . . ? N4 C3 C7' C10' -63.5(3) . . . . ? C2 C3 C7' C10' 168.0(2) . . . . ? C3A N4A C5A O2A 176.9(3) . . . . ? C3A N4A C5A C6A -4.1(4) . . . . ? N1A C6A C5A O2A 164.0(2) . . . . ? C7A C6A C5A O2A -68.4(3) . . . . ? N1A C6A C5A N4A -15.0(3) . . . . ? C7A C6A C5A N4A 112.7(3) . . . . ? N8B C15B C14B C13B 179.3(3) . . . . ? C16B C15B C14B C13B -2.7(4) . . . . ? C15B C14B C13B C12B 2.2(4) . . . . ? C3 N4 C5 O2 -169.6(3) . . . . ? C3 N4 C5 C6 11.0(4) . . . . ? C11 C16 C15 N8 -179.9(3) . . . . ? C10 C16 C15 N8 -0.3(3) . . . . ? C11 C16 C15 C14 -0.8(5) . . . . ? C10 C16 C15 C14 178.8(3) . . . . ? C9A N8A C15A C14A 178.2(3) . . . . ? C9A N8A C15A C16A -0.9(3) . . . . ? C11A C16A C15A N8A -179.7(2) . . . . ? C10A C16A C15A N8A 1.0(3) . . . . ? C11A C16A C15A C14A 1.1(4) . . . . ? C10A C16A C15A C14A -178.2(3) . . . . ? N8A C15A C14A C13A -179.3(3) . . . . ? C16A C15A C14A C13A -0.3(4) . . . . ? C16B C11B C12B C13B 1.0(4) . . . . ? C14B C13B C12B C11B -1.5(5) . . . . ? C15 C16 C10 C9 0.3(3) . . . . ? C11 C16 C10 C9 179.9(3) . . . . ? C15 C16 C10 C7 -179.6(3) . . . . ? C11 C16 C10 C7 -0.1(5) . . . . ? C6 C7 C10 C9 -88.8(4) . . . . ? C6 C7 C10 C16 91.1(4) . . . . ? C9B C10B C7B C3A 115.0(3) . . . . ? C16B C10B C7B C3A -67.1(3) . . . . ? N4A C3A C7B C10B -52.5(3) . . . . ? C2A C3A C7B C10B 179.8(2) . . . . ? C16 C10 C9 N8 -0.2(3) . . . . ? C7 C10 C9 N8 179.7(3) . . . . ? C16' C10' C9' N8' 0.1(3) . . . . ? C7' C10' C9' N8' 175.8(3) . . . . ? C15' N8' C9' C10' -1.0(3) . . . . ? C16' C11' C12' C13' 1.7(4) . . . . ? C14' C13' C12' C11' -3.1(5) . . . . ? C15A C14A C13A C12A -0.8(4) . . . . ? C11A C12A C13A C14A 1.1(4) . . . . ? C2 N1 C6 C5 23.7(4) . . . . ? C17 N1 C6 C5 -153.3(2) . . . . ? C2 N1 C6 C7 -103.3(3) . . . . ? C17 N1 C6 C7 79.7(3) . . . . ? O2 C5 C6 N1 154.8(2) . . . . ? N4 C5 C6 N1 -25.8(3) . . . . ? O2 C5 C6 C7 -78.0(3) . . . . ? N4 C5 C6 C7 101.4(3) . . . . ? C10 C7 C6 N1 61.1(3) . . . . ? C10 C7 C6 C5 -66.5(3) . . . . ? C15A N8A C9A C10A 0.4(3) . . . . ? C16A C10A C9A N8A 0.3(3) . . . . ? C7A C10A C9A N8A -177.8(2) . . . . ? C10 C9 N8 C15 0.1(4) . . . . ? C14 C15 N8 C9 -178.9(3) . . . . ? C16 C15 N8 C9 0.1(3) . . . . ? C15 C16 C11 C12 0.0(5) . . . . ? C10 C16 C11 C12 -179.5(3) . . . . ? C12 C13 C14 C15 -2.7(5) . . . . ? N8 C15 C14 C13 -178.9(3) . . . . ? C16 C15 C14 C13 2.1(5) . . . . ? C16 C11 C12 C13 -0.6(5) . . . . ? C14 C13 C12 C11 2.0(6) . . . . ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.500 -0.026 299 47 ' ' _platon_squeeze_details ; ; _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.217 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.047 _database_code_depnum_ccdc_archive 'CCDC 864569' ####################################################################### # # 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_Compound-8A #TrackingRef 'COMPOUND 8A.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common CMPWWSSR _chemical_melting_point ? _chemical_formula_moiety 'C31 H33 N7 O7, C O, O' _chemical_absolute_configuration rm _chemical_formula_sum 'C32 H33 N7 O9' _chemical_formula_weight 659.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.505(2) _cell_length_b 14.137(1) _cell_length_c 24.601(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2957.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 999 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 28.36 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type PSI-SCAN _exptl_absorpt_correction_T_min 0.9782 _exptl_absorpt_correction_T_max 0.9912 _exptl_absorpt_process_details '(North et al., 1968)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area Detector' _diffrn_measurement_method 'Phi-Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19274 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_sigmaI/netI 0.0683 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 28.36 _reflns_number_total 7246 _reflns_number_gt 5473 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SAINT 6.45 ( Bruker, 2003)' _computing_data_reduction 'SAINT 6.45 ( Bruker, 2003)' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'diamond 3.1d' _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^)+(0.0849P)^2^+1.6808P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.5(14) _refine_ls_number_reflns 7246 _refine_ls_number_parameters 441 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0891 _refine_ls_R_factor_gt 0.0638 _refine_ls_wR_factor_ref 0.1822 _refine_ls_wR_factor_gt 0.1573 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.088 _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 O3 O 0.0006(3) 0.64334(16) 0.66941(9) 0.0242(5) Uani 1 1 d . . . O5 O 0.0948(3) 0.37477(17) 0.60996(10) 0.0287(6) Uani 1 1 d . . . H5' H 0.1547 0.3403 0.6270 0.043 Uiso 1 1 calc R . . O1 O -0.2412(3) 0.71677(16) 0.83721(9) 0.0244(5) Uani 1 1 d . . . O2 O -0.2736(3) 0.45068(18) 0.98862(10) 0.0319(6) Uani 1 1 d . . . O4 O 0.0068(3) 0.54542(18) 0.56533(9) 0.0279(6) Uani 1 1 d . . . H4' H 0.0371 0.5013 0.5464 0.042 Uiso 1 1 calc R . . O6 O 0.2569(3) 0.44270(17) 0.70440(10) 0.0303(6) Uani 1 1 d . . . H6' H 0.2950 0.3999 0.6861 0.046 Uiso 1 1 calc R . . N20 N -0.2381(3) 0.56822(19) 0.68847(11) 0.0218(6) Uani 1 1 d . . . N1 N -0.3305(3) 0.57186(19) 0.86053(11) 0.0213(6) Uani 1 1 d . . . N4 N -0.1413(4) 0.5735(2) 0.95228(12) 0.0233(6) Uani 1 1 d . . . N21 N -0.3248(4) 0.4889(2) 0.68600(12) 0.0301(7) Uani 1 1 d . . . N8 N 0.0892(4) 0.3813(2) 0.80134(13) 0.0285(7) Uani 1 1 d . . . N8' N 0.3588(3) 0.5727(2) 0.98165(11) 0.0230(6) Uani 1 1 d . . . H8' H 0.4024 0.5408 1.0073 0.028 Uiso 1 1 calc R . . N22 N -0.4101(3) 0.4866(2) 0.73112(12) 0.0281(7) Uani 1 1 d . . . C24 C -0.0730(4) 0.5094(2) 0.61179(13) 0.0231(7) Uani 1 1 d . . . H24 H -0.1655 0.4732 0.6003 0.028 Uiso 1 1 calc R . . C13' C 0.5615(4) 0.7989(3) 0.95187(14) 0.0273(8) Uani 1 1 d . . . H13' H 0.6472 0.8366 0.9609 0.033 Uiso 1 1 calc R . . O7 O 0.3405(3) 0.6731(2) 0.69441(13) 0.0435(7) Uani 1 1 d . . . H7' H 0.4041 0.7074 0.7098 0.065 Uiso 1 1 calc R . . C7' C 0.0506(4) 0.6133(3) 0.87857(13) 0.0233(7) Uani 1 1 d . . . H7'A H 0.0392 0.5511 0.8624 0.028 Uiso 1 1 calc R . . H7'B H 0.0682 0.6582 0.8494 0.028 Uiso 1 1 calc R . . C9' C 0.2296(4) 0.5450(2) 0.95261(13) 0.0242(7) Uani 1 1 d . . . H9' H 0.1758 0.4883 0.9575 0.029 Uiso 1 1 calc R . . C15' C 0.4083(4) 0.6599(2) 0.96323(13) 0.0220(7) Uani 1 1 d . . . C23 C -0.1245(4) 0.5951(2) 0.64502(13) 0.0226(7) Uani 1 1 d . . . H23 H -0.1778 0.6391 0.6204 0.027 Uiso 1 1 calc R . . C5 C -0.2480(4) 0.5043(3) 0.95006(13) 0.0246(7) Uani 1 1 d . . . C19 C -0.2664(4) 0.6170(2) 0.73448(12) 0.0220(7) Uani 1 1 d . . . H19 H -0.2221 0.6741 0.7453 0.026 Uiso 1 1 calc R . . C10 C -0.1281(4) 0.3833(2) 0.85362(14) 0.0243(7) Uani 1 1 d . . . C10' C 0.1912(4) 0.6131(2) 0.91529(13) 0.0228(7) Uani 1 1 d . . . C16' C 0.3037(4) 0.6876(2) 0.92156(13) 0.0206(7) Uani 1 1 d . . . C6 C -0.3388(4) 0.4898(2) 0.89770(13) 0.0241(7) Uani 1 1 d . . . H6 H -0.4494 0.4843 0.9083 0.029 Uiso 1 1 calc R . . C2 C -0.2329(4) 0.6461(2) 0.86700(12) 0.0213(6) Uani 1 1 d . . . C12' C 0.4583(4) 0.8286(3) 0.91018(14) 0.0260(7) Uani 1 1 d . . . H12' H 0.4766 0.8859 0.8927 0.031 Uiso 1 1 calc R . . C3 C -0.1047(4) 0.6397(2) 0.90856(14) 0.0223(7) Uani 1 1 d . . . H3 H -0.0911 0.7025 0.9247 0.027 Uiso 1 1 calc R . . C18 C -0.3759(4) 0.5632(2) 0.76186(14) 0.0232(7) Uani 1 1 d . . . C11' C 0.3315(4) 0.7745(2) 0.89487(13) 0.0228(7) Uani 1 1 d . . . H11' H 0.2649 0.7949 0.8673 0.027 Uiso 1 1 calc R . . C14' C 0.5371(4) 0.7150(3) 0.97933(13) 0.0243(7) Uani 1 1 d . . . H14' H 0.6033 0.6959 1.0073 0.029 Uiso 1 1 calc R . . C16 C 0.0021(4) 0.3517(2) 0.88603(15) 0.0252(7) Uani 1 1 d . . . C27 C 0.0986(4) 0.5846(2) 0.70360(15) 0.0265(7) Uani 1 1 d . . . H27 H 0.0325 0.5565 0.7320 0.032 Uiso 1 1 calc R . . C9 C -0.0700(4) 0.3996(2) 0.80296(15) 0.0253(7) Uani 1 1 d . . . H9 H -0.1294 0.4203 0.7735 0.030 Uiso 1 1 calc R . . C13 C 0.2976(4) 0.2954(3) 0.92380(17) 0.0332(9) Uani 1 1 d . . . H13 H 0.3951 0.2772 0.9373 0.040 Uiso 1 1 calc R . . C7 C -0.2960(4) 0.3952(2) 0.87075(14) 0.0251(7) Uani 1 1 d . . . H7A H -0.3218 0.3447 0.8959 0.030 Uiso 1 1 calc R . . H7B H -0.3621 0.3873 0.8389 0.030 Uiso 1 1 calc R . . C26 C 0.1685(4) 0.5052(2) 0.66974(14) 0.0255(7) Uani 1 1 d . . . H26 H 0.2365 0.5312 0.6413 0.031 Uiso 1 1 calc R . . C17 C -0.4475(4) 0.5773(3) 0.81718(14) 0.0247(7) Uani 1 1 d . . . H17B H -0.4984 0.6386 0.8184 0.030 Uiso 1 1 calc R . . H17A H -0.5272 0.5294 0.8232 0.030 Uiso 1 1 calc R . . C15 C 0.1364(4) 0.3527(2) 0.85239(15) 0.0271(7) Uani 1 1 d . . . C25 C 0.0374(4) 0.4462(2) 0.64448(14) 0.0232(7) Uani 1 1 d . . . H25 H -0.0229 0.4164 0.6738 0.028 Uiso 1 1 calc R . . C11 C 0.0184(5) 0.3186(3) 0.93973(16) 0.0311(8) Uani 1 1 d . . . H11 H -0.0686 0.3150 0.9625 0.037 Uiso 1 1 calc R . . C12 C 0.1653(5) 0.2917(3) 0.95814(17) 0.0346(9) Uani 1 1 d . . . H12 H 0.1769 0.2707 0.9937 0.042 Uiso 1 1 calc R . . C14 C 0.2858(4) 0.3254(2) 0.87072(16) 0.0299(8) Uani 1 1 d . . . H14 H 0.3732 0.3276 0.8480 0.036 Uiso 1 1 calc R . . C28 C 0.2195(5) 0.6488(3) 0.73071(16) 0.0346(9) Uani 1 1 d . . . H28A H 0.1681 0.7060 0.7434 0.041 Uiso 1 1 calc R . . H28B H 0.2641 0.6168 0.7620 0.041 Uiso 1 1 calc R . . O1W O 0.5230(4) 0.7928(2) 0.75746(14) 0.0539(8) Uani 1 1 d . . . O1A O 0.1654(12) 0.3293(4) 1.0855(3) 0.169(4) Uani 1 1 d D . . C1A C 0.0521(13) 0.4089(6) 1.0728(4) 0.118(3) Uani 1 1 d D . . H4 H -0.086(5) 0.582(3) 0.9830(18) 0.037(12) Uiso 1 1 d . . . H8 H 0.151(5) 0.386(3) 0.7779(15) 0.015(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 O3 0.0265(12) 0.0184(11) 0.0279(12) -0.0012(9) 0.0000(10) -0.0025(10) O5 0.0369(14) 0.0234(13) 0.0258(12) -0.0054(10) 0.0001(11) 0.0098(11) O1 0.0304(12) 0.0203(12) 0.0227(11) -0.0021(9) -0.0017(11) -0.0004(10) O2 0.0346(14) 0.0313(14) 0.0297(12) 0.0081(11) 0.0047(12) 0.0008(11) O4 0.0377(14) 0.0236(13) 0.0225(11) -0.0010(10) 0.0080(11) 0.0068(11) O6 0.0263(12) 0.0252(13) 0.0395(13) -0.0049(11) -0.0013(12) 0.0040(10) N20 0.0246(14) 0.0185(13) 0.0222(12) -0.0042(11) 0.0006(12) -0.0012(11) N1 0.0226(13) 0.0218(14) 0.0195(12) 0.0009(11) 0.0001(11) 0.0003(11) N4 0.0252(14) 0.0243(15) 0.0204(13) -0.0001(11) -0.0047(12) -0.0007(12) N21 0.0308(16) 0.0280(16) 0.0315(15) -0.0074(13) 0.0038(14) -0.0068(13) N8 0.0255(15) 0.0271(16) 0.0330(17) -0.0001(14) 0.0061(14) 0.0023(13) N8' 0.0251(14) 0.0227(15) 0.0211(13) 0.0007(11) -0.0030(12) 0.0024(12) N22 0.0236(15) 0.0317(16) 0.0289(15) -0.0036(13) 0.0031(12) -0.0040(12) C24 0.0256(16) 0.0240(17) 0.0197(15) 0.0004(13) -0.0001(13) 0.0043(13) C13' 0.0277(18) 0.0282(19) 0.0261(17) -0.0086(14) 0.0033(15) -0.0061(14) O7 0.0348(15) 0.0397(17) 0.0561(18) -0.0120(14) 0.0002(15) -0.0091(13) C7' 0.0238(16) 0.0253(17) 0.0208(15) 0.0005(13) -0.0023(13) -0.0037(13) C9' 0.0262(17) 0.0208(16) 0.0256(16) -0.0024(13) 0.0004(14) -0.0015(13) C15' 0.0236(16) 0.0211(16) 0.0212(15) -0.0025(13) 0.0027(13) 0.0027(13) C23 0.0254(17) 0.0204(16) 0.0221(15) -0.0007(13) -0.0001(13) 0.0000(13) C5 0.0217(15) 0.0260(17) 0.0260(16) 0.0024(13) 0.0018(14) 0.0041(13) C19 0.0226(15) 0.0217(16) 0.0217(15) -0.0043(13) -0.0066(14) 0.0014(13) C10 0.0258(17) 0.0151(15) 0.0320(17) -0.0017(13) 0.0011(14) -0.0012(13) C10' 0.0264(17) 0.0237(17) 0.0183(14) -0.0031(13) 0.0031(13) -0.0012(13) C16' 0.0215(16) 0.0204(16) 0.0199(15) -0.0015(12) 0.0013(13) 0.0034(12) C6 0.0230(16) 0.0234(17) 0.0257(16) 0.0017(14) 0.0043(14) -0.0038(13) C2 0.0251(16) 0.0199(15) 0.0190(14) -0.0035(12) 0.0038(14) 0.0004(13) C12' 0.0281(17) 0.0235(18) 0.0264(16) -0.0013(14) 0.0021(14) -0.0005(14) C3 0.0229(16) 0.0200(16) 0.0239(16) 0.0009(13) -0.0038(13) -0.0003(13) C18 0.0209(16) 0.0240(17) 0.0246(16) -0.0037(14) -0.0050(13) 0.0017(13) C11' 0.0252(16) 0.0212(16) 0.0220(15) -0.0013(13) -0.0006(14) 0.0021(13) C14' 0.0221(16) 0.0290(18) 0.0217(15) -0.0041(14) 0.0008(13) 0.0046(14) C16 0.0252(16) 0.0159(15) 0.0346(18) -0.0005(14) -0.0013(15) -0.0013(13) C27 0.0266(17) 0.0233(17) 0.0297(17) 0.0012(14) -0.0032(15) -0.0010(14) C9 0.0244(17) 0.0194(16) 0.0322(18) -0.0029(14) -0.0021(14) 0.0017(13) C13 0.0290(19) 0.0213(18) 0.049(2) 0.0004(16) -0.0060(17) 0.0020(14) C7 0.0234(16) 0.0210(16) 0.0307(17) -0.0007(14) 0.0009(14) -0.0029(13) C26 0.0238(16) 0.0232(17) 0.0294(17) -0.0003(14) -0.0008(14) -0.0027(14) C17 0.0188(15) 0.0285(18) 0.0268(16) -0.0001(14) 0.0006(14) 0.0004(13) C15 0.0274(17) 0.0178(16) 0.0362(19) -0.0002(14) -0.0012(16) -0.0001(13) C25 0.0238(16) 0.0218(16) 0.0239(15) -0.0040(13) -0.0006(13) 0.0023(13) C11 0.0308(19) 0.0206(17) 0.042(2) 0.0084(16) 0.0040(17) -0.0027(15) C12 0.039(2) 0.0223(18) 0.042(2) 0.0088(16) -0.0027(18) 0.0021(16) C14 0.0209(17) 0.0217(17) 0.047(2) 0.0014(16) 0.0020(16) -0.0016(13) C28 0.037(2) 0.0278(19) 0.039(2) -0.0091(16) -0.0089(18) 0.0005(16) O1W 0.059(2) 0.0460(19) 0.0567(19) -0.0027(16) -0.0068(17) 0.0006(16) O1A 0.311(11) 0.083(4) 0.111(4) -0.014(3) -0.036(6) 0.068(6) C1A 0.159(9) 0.062(5) 0.132(7) 0.001(5) -0.011(6) -0.012(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O3 C23 1.400(4) . ? O3 C27 1.446(4) . ? O5 C25 1.407(4) . ? O1 C2 1.241(4) . ? O2 C5 1.234(4) . ? O4 C24 1.423(4) . ? O6 C26 1.440(4) . ? N20 N21 1.344(4) . ? N20 C19 1.347(4) . ? N20 C23 1.490(4) . ? N1 C2 1.347(4) . ? N1 C17 1.460(4) . ? N1 C6 1.479(4) . ? N4 C5 1.335(5) . ? N4 C3 1.459(4) . ? N21 N22 1.326(4) . ? N8 C15 1.379(5) . ? N8 C9 1.380(5) . ? N8' C9' 1.368(4) . ? N8' C15' 1.380(4) . ? N22 C18 1.352(4) . ? C24 C23 1.525(4) . ? C24 C25 1.526(5) . ? C13' C14' 1.380(5) . ? C13' C12' 1.413(5) . ? O7 C28 1.405(5) . ? C7' C10' 1.499(5) . ? C7' C3 1.558(5) . ? C9' C10' 1.370(5) . ? C15' C14' 1.401(5) . ? C15' C16' 1.413(5) . ? C5 C6 1.516(5) . ? C19 C18 1.378(5) . ? C10 C9 1.360(5) . ? C10 C16 1.436(5) . ? C10 C7 1.499(5) . ? C10' C16' 1.431(5) . ? C16' C11' 1.413(5) . ? C6 C7 1.536(5) . ? C2 C3 1.497(5) . ? C12' C11' 1.374(5) . ? C18 C17 1.504(5) . ? C16 C11 1.408(5) . ? C16 C15 1.411(5) . ? C27 C26 1.519(5) . ? C27 C28 1.526(5) . ? C13 C14 1.377(5) . ? C13 C12 1.408(6) . ? C26 C25 1.525(5) . ? C15 C14 1.402(5) . ? C11 C12 1.382(5) . ? O1A C1A 1.514(10) . ? 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 C23 O3 C27 114.0(2) . . ? N21 N20 C19 111.6(3) . . ? N21 N20 C23 122.4(3) . . ? C19 N20 C23 126.0(3) . . ? C2 N1 C17 117.7(3) . . ? C2 N1 C6 124.5(3) . . ? C17 N1 C6 117.4(3) . . ? C5 N4 C3 125.8(3) . . ? N22 N21 N20 106.4(3) . . ? C15 N8 C9 108.3(3) . . ? C9' N8' C15' 109.2(3) . . ? N21 N22 C18 109.3(3) . . ? O4 C24 C23 106.5(3) . . ? O4 C24 C25 109.8(3) . . ? C23 C24 C25 111.1(3) . . ? C14' C13' C12' 121.1(3) . . ? C10' C7' C3 113.1(3) . . ? N8' C9' C10' 109.9(3) . . ? N8' C15' C14' 130.0(3) . . ? N8' C15' C16' 107.1(3) . . ? C14' C15' C16' 122.9(3) . . ? O3 C23 N20 108.0(2) . . ? O3 C23 C24 113.5(3) . . ? N20 C23 C24 111.6(3) . . ? O2 C5 N4 122.6(3) . . ? O2 C5 C6 118.7(3) . . ? N4 C5 C6 118.7(3) . . ? N20 C19 C18 104.4(3) . . ? C9 C10 C16 106.4(3) . . ? C9 C10 C7 125.8(3) . . ? C16 C10 C7 127.8(3) . . ? C9' C10' C16' 106.6(3) . . ? C9' C10' C7' 126.6(3) . . ? C16' C10' C7' 126.6(3) . . ? C15' C16' C11' 118.2(3) . . ? C15' C16' C10' 107.2(3) . . ? C11' C16' C10' 134.6(3) . . ? N1 C6 C5 113.3(3) . . ? N1 C6 C7 113.9(3) . . ? C5 C6 C7 111.3(3) . . ? O1 C2 N1 121.5(3) . . ? O1 C2 C3 119.5(3) . . ? N1 C2 C3 118.8(3) . . ? C11' C12' C13' 121.4(3) . . ? N4 C3 C2 112.7(3) . . ? N4 C3 C7' 112.1(3) . . ? C2 C3 C7' 108.0(3) . . ? N22 C18 C19 108.3(3) . . ? N22 C18 C17 121.7(3) . . ? C19 C18 C17 129.9(3) . . ? C12' C11' C16' 119.2(3) . . ? C13' C14' C15' 117.2(3) . . ? C11 C16 C15 118.3(3) . . ? C11 C16 C10 134.5(3) . . ? C15 C16 C10 107.2(3) . . ? O3 C27 C26 109.3(3) . . ? O3 C27 C28 107.5(3) . . ? C26 C27 C28 114.6(3) . . ? C10 C9 N8 110.5(3) . . ? C14 C13 C12 121.5(3) . . ? C10 C7 C6 116.4(3) . . ? O6 C26 C27 109.5(3) . . ? O6 C26 C25 106.7(3) . . ? C27 C26 C25 110.0(3) . . ? N1 C17 C18 112.2(3) . . ? N8 C15 C14 129.6(4) . . ? N8 C15 C16 107.5(3) . . ? C14 C15 C16 122.9(3) . . ? O5 C25 C26 112.6(3) . . ? O5 C25 C24 108.4(3) . . ? C26 C25 C24 110.1(3) . . ? C12 C11 C16 119.2(4) . . ? C11 C12 C13 121.0(3) . . ? C13 C14 C15 117.1(3) . . ? O7 C28 C27 111.2(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C19 N20 N21 N22 0.0(4) . . . . ? C23 N20 N21 N22 179.1(3) . . . . ? N20 N21 N22 C18 -0.7(4) . . . . ? C15' N8' C9' C10' -0.5(4) . . . . ? C9' N8' C15' C14' -178.0(3) . . . . ? C9' N8' C15' C16' 0.8(4) . . . . ? C27 O3 C23 N20 68.6(3) . . . . ? C27 O3 C23 C24 -55.7(4) . . . . ? N21 N20 C23 O3 -147.6(3) . . . . ? C19 N20 C23 O3 31.4(4) . . . . ? N21 N20 C23 C24 -22.1(4) . . . . ? C19 N20 C23 C24 156.9(3) . . . . ? O4 C24 C23 O3 -69.7(3) . . . . ? C25 C24 C23 O3 49.9(4) . . . . ? O4 C24 C23 N20 168.0(3) . . . . ? C25 C24 C23 N20 -72.5(4) . . . . ? C3 N4 C5 O2 -179.9(3) . . . . ? C3 N4 C5 C6 1.4(5) . . . . ? N21 N20 C19 C18 0.7(4) . . . . ? C23 N20 C19 C18 -178.4(3) . . . . ? N8' C9' C10' C16' 0.0(4) . . . . ? N8' C9' C10' C7' -175.0(3) . . . . ? C3 C7' C10' C9' 75.8(4) . . . . ? C3 C7' C10' C16' -98.2(4) . . . . ? N8' C15' C16' C11' -178.5(3) . . . . ? C14' C15' C16' C11' 0.4(5) . . . . ? N8' C15' C16' C10' -0.8(3) . . . . ? C14' C15' C16' C10' 178.1(3) . . . . ? C9' C10' C16' C15' 0.5(4) . . . . ? C7' C10' C16' C15' 175.5(3) . . . . ? C9' C10' C16' C11' 177.6(4) . . . . ? C7' C10' C16' C11' -7.3(6) . . . . ? C2 N1 C6 C5 10.6(4) . . . . ? C17 N1 C6 C5 -162.7(3) . . . . ? C2 N1 C6 C7 -118.0(3) . . . . ? C17 N1 C6 C7 68.7(4) . . . . ? O2 C5 C6 N1 164.4(3) . . . . ? N4 C5 C6 N1 -16.8(4) . . . . ? O2 C5 C6 C7 -65.7(4) . . . . ? N4 C5 C6 C7 113.0(3) . . . . ? C17 N1 C2 O1 -0.1(5) . . . . ? C6 N1 C2 O1 -173.4(3) . . . . ? C17 N1 C2 C3 -175.8(3) . . . . ? C6 N1 C2 C3 10.9(5) . . . . ? C14' C13' C12' C11' -1.0(5) . . . . ? C5 N4 C3 C2 19.7(5) . . . . ? C5 N4 C3 C7' -102.4(4) . . . . ? O1 C2 C3 N4 158.9(3) . . . . ? N1 C2 C3 N4 -25.4(4) . . . . ? O1 C2 C3 C7' -76.7(4) . . . . ? N1 C2 C3 C7' 99.1(3) . . . . ? C10' C7' C3 N4 -60.2(4) . . . . ? C10' C7' C3 C2 175.0(3) . . . . ? N21 N22 C18 C19 1.2(4) . . . . ? N21 N22 C18 C17 -176.4(3) . . . . ? N20 C19 C18 N22 -1.1(4) . . . . ? N20 C19 C18 C17 176.2(3) . . . . ? C13' C12' C11' C16' 0.2(5) . . . . ? C15' C16' C11' C12' 0.1(5) . . . . ? C10' C16' C11' C12' -176.9(3) . . . . ? C12' C13' C14' C15' 1.4(5) . . . . ? N8' C15' C14' C13' 177.5(3) . . . . ? C16' C15' C14' C13' -1.2(5) . . . . ? C9 C10 C16 C11 -175.5(4) . . . . ? C7 C10 C16 C11 3.6(6) . . . . ? C9 C10 C16 C15 1.3(4) . . . . ? C7 C10 C16 C15 -179.6(3) . . . . ? C23 O3 C27 C26 59.9(3) . . . . ? C23 O3 C27 C28 -175.2(3) . . . . ? C16 C10 C9 N8 -0.6(4) . . . . ? C7 C10 C9 N8 -179.8(3) . . . . ? C15 N8 C9 C10 -0.3(4) . . . . ? C9 C10 C7 C6 -95.8(4) . . . . ? C16 C10 C7 C6 85.2(4) . . . . ? N1 C6 C7 C10 67.7(4) . . . . ? C5 C6 C7 C10 -61.9(4) . . . . ? O3 C27 C26 O6 -175.9(3) . . . . ? C28 C27 C26 O6 63.4(4) . . . . ? O3 C27 C26 C25 -59.0(4) . . . . ? C28 C27 C26 C25 -179.7(3) . . . . ? C2 N1 C17 C18 74.8(4) . . . . ? C6 N1 C17 C18 -111.5(3) . . . . ? N22 C18 C17 N1 113.5(4) . . . . ? C19 C18 C17 N1 -63.5(5) . . . . ? C9 N8 C15 C14 179.2(4) . . . . ? C9 N8 C15 C16 1.1(4) . . . . ? C11 C16 C15 N8 175.9(3) . . . . ? C10 C16 C15 N8 -1.5(4) . . . . ? C11 C16 C15 C14 -2.3(5) . . . . ? C10 C16 C15 C14 -179.8(3) . . . . ? O6 C26 C25 O5 -64.9(3) . . . . ? C27 C26 C25 O5 176.4(3) . . . . ? O6 C26 C25 C24 173.9(3) . . . . ? C27 C26 C25 C24 55.3(4) . . . . ? O4 C24 C25 O5 -55.8(3) . . . . ? C23 C24 C25 O5 -173.3(3) . . . . ? O4 C24 C25 C26 67.8(3) . . . . ? C23 C24 C25 C26 -49.7(4) . . . . ? C15 C16 C11 C12 2.3(5) . . . . ? C10 C16 C11 C12 178.8(4) . . . . ? C16 C11 C12 C13 -1.0(6) . . . . ? C14 C13 C12 C11 -0.4(6) . . . . ? C12 C13 C14 C15 0.4(5) . . . . ? N8 C15 C14 C13 -176.9(4) . . . . ? C16 C15 C14 C13 1.0(5) . . . . ? O3 C27 C28 O7 -77.2(4) . . . . ? C26 C27 C28 O7 44.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.36 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.537 _refine_diff_density_min -0.534 _refine_diff_density_rms 0.091 _database_code_depnum_ccdc_archive 'CCDC 864568'