# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # 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_syn_isomer _database_code_depnum_ccdc_archive 'CCDC 896704' #TrackingRef '467iso.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H44 N6 O' _chemical_formula_weight 600.79 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.477(3) _cell_length_b 12.939(3) _cell_length_c 13.929(3) _cell_angle_alpha 111.981(7) _cell_angle_beta 99.220(7) _cell_angle_gamma 101.616(7) _cell_volume 1656.5(7) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 19934 _cell_measurement_theta_min 1.63 _cell_measurement_theta_max 25.00 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.205 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 644 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9568 _exptl_absorpt_correction_T_max 0.9839 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-APEX-II CCD area detector' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19934 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5807 _reflns_number_gt 3947 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0576P)^2^+0.5184P] 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 5807 _refine_ls_number_parameters 424 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0799 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.1315 _refine_ls_wR_factor_gt 0.1151 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 O1 O 0.52903(19) 0.50642(16) 0.74471(15) 0.0641(5) Uani 1 1 d D . . H1W H 0.610(2) 0.485(2) 0.723(2) 0.077 Uiso 1 1 d D . . H2W H 0.538(3) 0.577(2) 0.729(2) 0.077 Uiso 1 1 d D . . C1 C 0.6318(2) 0.77924(18) 0.34258(16) 0.0354(5) Uani 1 1 d . . . C2 C 0.5044(2) 0.7549(2) 0.28228(18) 0.0472(6) Uani 1 1 d . . . H026 H 0.4325 0.7751 0.3085 0.057 Uiso 1 1 calc R . . C3 C 0.4999(2) 0.6936(2) 0.17321(18) 0.0471(6) Uani 1 1 d . . . H020 H 0.4250 0.6664 0.1152 0.056 Uiso 1 1 calc R . . C4 C 0.6251(2) 0.68177(18) 0.16855(16) 0.0353(5) Uani 1 1 d . . . C5 C 0.6807(2) 0.62759(18) 0.07512(16) 0.0380(5) Uani 1 1 d . . . H5 H 0.6062 0.5958 0.0103 0.046 Uiso 1 1 calc R . . C6 C 0.7883(2) 0.71820(19) 0.06491(17) 0.0400(5) Uani 1 1 d . . . C7 C 0.7769(3) 0.7348(2) -0.0282(2) 0.0578(7) Uani 1 1 d . . . H44 H 0.7028 0.6902 -0.0868 0.069 Uiso 1 1 calc R . . C8 C 0.8772(3) 0.8186(3) -0.0327(3) 0.0762(9) Uani 1 1 d . . . H034 H 0.8716 0.8313 -0.0946 0.091 Uiso 1 1 calc R . . C9 C 0.9839(3) 0.8824(3) 0.0535(3) 0.0740(9) Uani 1 1 d . . . H038 H 1.0520 0.9401 0.0523 0.089 Uiso 1 1 calc R . . C10 C 0.9895(3) 0.8603(2) 0.1430(2) 0.0674(8) Uani 1 1 d . . . H036 H 1.0636 0.9039 0.2017 0.081 Uiso 1 1 calc R . . C11 C 0.7346(2) 0.52845(18) 0.07680(15) 0.0347(5) Uani 1 1 d . . . C12 C 0.8358(2) 0.49105(19) 0.03733(17) 0.0439(6) Uani 1 1 d . . . H018 H 0.8925 0.5263 0.0065 0.053 Uiso 1 1 calc R . . C13 C 0.8394(2) 0.3893(2) 0.05167(18) 0.0451(6) Uani 1 1 d . . . H021 H 0.8991 0.3459 0.0319 0.054 Uiso 1 1 calc R . . C14 C 0.7403(2) 0.36540(17) 0.09948(15) 0.0338(5) Uani 1 1 d . . . C15 C 0.6915(2) 0.26204(17) 0.12459(15) 0.0352(5) Uani 1 1 d . . . C16 C 0.5800(2) 0.16604(19) 0.02629(16) 0.0447(6) Uani 1 1 d . . . H02C H 0.5409 0.1052 0.0466 0.054 Uiso 1 1 calc R . . H02D H 0.5092 0.1995 0.0095 0.054 Uiso 1 1 calc R . . C17 C 0.6248(3) 0.1103(2) -0.07504(19) 0.0614(7) Uani 1 1 d . . . H03C H 0.5489 0.0522 -0.1305 0.092 Uiso 1 1 calc R . . H03D H 0.6932 0.0749 -0.0605 0.092 Uiso 1 1 calc R . . H03E H 0.6604 0.1688 -0.0981 0.092 Uiso 1 1 calc R . . C18 C 0.8134(2) 0.2170(2) 0.15060(19) 0.0500(6) Uani 1 1 d . . . H03A H 0.8510 0.1954 0.0891 0.060 Uiso 1 1 calc R . . H03B H 0.8823 0.2803 0.2101 0.060 Uiso 1 1 calc R . . C19 C 0.7817(3) 0.1138(3) 0.1790(3) 0.0788(9) Uani 1 1 d . . . H03F H 0.8627 0.0924 0.1941 0.118 Uiso 1 1 calc R . . H03G H 0.7160 0.0494 0.1198 0.118 Uiso 1 1 calc R . . H03H H 0.7466 0.1345 0.2410 0.118 Uiso 1 1 calc R . . C20 C 0.6325(2) 0.29497(17) 0.21990(16) 0.0359(5) Uani 1 1 d . . . C21 C 0.5144(2) 0.24468(19) 0.23572(18) 0.0447(6) Uani 1 1 d . . . H019 H 0.4452 0.1816 0.1840 0.054 Uiso 1 1 calc R . . C22 C 0.5155(2) 0.3049(2) 0.34416(18) 0.0460(6) Uani 1 1 d . . . H024 H 0.4472 0.2886 0.3761 0.055 Uiso 1 1 calc R . . C23 C 0.6342(2) 0.39124(18) 0.39369(16) 0.0370(5) Uani 1 1 d . . . C24 C 0.6862(2) 0.47713(18) 0.50934(16) 0.0370(5) Uani 1 1 d . . . H24 H 0.6074 0.4774 0.5388 0.044 Uiso 1 1 calc R . . C25 C 0.7831(2) 0.44069(19) 0.57595(16) 0.0398(5) Uani 1 1 d . . . C26 C 0.8859(3) 0.3984(2) 0.5413(2) 0.0553(7) Uani 1 1 d . . . H028 H 0.8984 0.3909 0.4746 0.066 Uiso 1 1 calc R . . C27 C 0.9701(3) 0.3672(2) 0.6053(2) 0.0614(7) Uani 1 1 d . . . H031 H 1.0403 0.3394 0.5828 0.074 Uiso 1 1 calc R . . C28 C 0.9490(3) 0.3779(3) 0.7020(2) 0.0689(8) Uani 1 1 d . . . H037 H 1.0039 0.3572 0.7469 0.083 Uiso 1 1 calc R . . C29 C 0.8447(3) 0.4197(3) 0.7313(2) 0.0788(9) Uani 1 1 d . . . H032 H 0.8300 0.4266 0.7972 0.095 Uiso 1 1 calc R . . C30 C 0.7463(2) 0.60144(18) 0.52656(16) 0.0367(5) Uani 1 1 d . . . C31 C 0.8508(2) 0.6886(2) 0.60553(18) 0.0473(6) Uani 1 1 d . . . H016 H 0.9093 0.6810 0.6586 0.057 Uiso 1 1 calc R . . C32 C 0.8544(2) 0.7919(2) 0.59265(18) 0.0474(6) Uani 1 1 d . . . H027 H 0.9159 0.8643 0.6356 0.057 Uiso 1 1 calc R . . C33 C 0.7514(2) 0.76755(18) 0.50585(16) 0.0359(5) Uani 1 1 d . . . C34 C 0.6977(2) 0.84521(17) 0.46148(16) 0.0359(5) Uani 1 1 d . . . C35 C 0.5889(2) 0.8863(2) 0.51729(17) 0.0444(6) Uani 1 1 d . . . H01A H 0.5470 0.9272 0.4815 0.053 Uiso 1 1 calc R . . H01B H 0.5195 0.8181 0.5069 0.053 Uiso 1 1 calc R . . C36 C 0.6379(3) 0.9651(2) 0.63672(19) 0.0622(7) Uani 1 1 d . . . H02E H 0.5630 0.9852 0.6632 0.093 Uiso 1 1 calc R . . H02F H 0.7043 1.0346 0.6484 0.093 Uiso 1 1 calc R . . H02G H 0.6771 0.9251 0.6739 0.093 Uiso 1 1 calc R . . C37 C 0.8162(2) 0.9501(2) 0.48022(19) 0.0510(6) Uani 1 1 d . . . H02A H 0.8580 0.9921 0.5566 0.061 Uiso 1 1 calc R . . H02B H 0.8833 0.9208 0.4463 0.061 Uiso 1 1 calc R . . C38 C 0.7759(3) 1.0351(2) 0.4374(3) 0.0801(9) Uani 1 1 d . . . H04A H 0.8544 1.0972 0.4521 0.120 Uiso 1 1 calc R . . H04B H 0.7113 1.0663 0.4719 0.120 Uiso 1 1 calc R . . H04C H 0.7368 0.9950 0.3615 0.120 Uiso 1 1 calc R . . N1 N 0.70399(18) 0.73289(15) 0.27224(13) 0.0368(4) Uani 1 1 d D . . H1 H 0.7898(16) 0.7459(19) 0.2877(17) 0.044 Uiso 1 1 d D . . N2 N 0.67633(17) 0.45111(15) 0.11423(13) 0.0340(4) Uani 1 1 d D . . H2 H 0.6141(18) 0.4591(18) 0.1480(16) 0.041 Uiso 1 1 d D . . N3 N 0.70506(18) 0.38462(15) 0.31751(13) 0.0369(4) Uani 1 1 d D . . H3 H 0.7836(17) 0.4297(17) 0.3279(17) 0.044 Uiso 1 1 d D . . N4 N 0.68638(18) 0.65034(15) 0.46655(13) 0.0351(4) Uani 1 1 d D . . H4 H 0.6214(18) 0.6094(17) 0.4083(14) 0.042 Uiso 1 1 d D . . N5 N 0.7616(2) 0.4518(2) 0.67012(15) 0.0607(6) Uani 1 1 d . . . N6 N 0.8943(2) 0.77948(18) 0.15002(16) 0.0557(5) 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 O1 0.0596(12) 0.0672(12) 0.0718(13) 0.0302(10) 0.0232(10) 0.0245(10) C1 0.0373(12) 0.0360(12) 0.0370(12) 0.0158(9) 0.0129(10) 0.0156(9) C2 0.0401(13) 0.0530(15) 0.0472(14) 0.0144(12) 0.0127(11) 0.0227(11) C3 0.0408(13) 0.0549(15) 0.0383(13) 0.0133(11) 0.0019(10) 0.0177(11) C4 0.0409(12) 0.0356(11) 0.0308(11) 0.0150(9) 0.0073(9) 0.0132(10) C5 0.0397(12) 0.0414(12) 0.0297(11) 0.0144(10) 0.0059(9) 0.0087(10) C6 0.0491(14) 0.0397(12) 0.0365(12) 0.0173(10) 0.0156(11) 0.0178(11) C7 0.0671(17) 0.0672(17) 0.0538(15) 0.0364(14) 0.0220(13) 0.0235(14) C8 0.097(2) 0.082(2) 0.088(2) 0.061(2) 0.050(2) 0.035(2) C9 0.079(2) 0.0550(18) 0.110(3) 0.0443(19) 0.055(2) 0.0223(16) C10 0.0549(17) 0.0537(16) 0.083(2) 0.0215(15) 0.0234(15) 0.0042(13) C11 0.0375(12) 0.0372(12) 0.0285(11) 0.0135(9) 0.0093(9) 0.0087(9) C12 0.0443(13) 0.0457(14) 0.0455(13) 0.0191(11) 0.0233(11) 0.0119(11) C13 0.0421(13) 0.0465(14) 0.0526(14) 0.0197(11) 0.0235(11) 0.0183(11) C14 0.0361(12) 0.0339(11) 0.0314(11) 0.0108(9) 0.0106(9) 0.0143(9) C15 0.0400(12) 0.0352(11) 0.0304(11) 0.0116(9) 0.0105(9) 0.0139(9) C16 0.0569(15) 0.0341(12) 0.0347(12) 0.0092(10) 0.0095(11) 0.0077(11) C17 0.0807(19) 0.0500(15) 0.0399(14) 0.0068(12) 0.0175(13) 0.0129(14) C18 0.0550(15) 0.0569(15) 0.0477(14) 0.0230(12) 0.0176(12) 0.0303(12) C19 0.095(2) 0.081(2) 0.096(2) 0.0569(19) 0.0349(19) 0.0545(19) C20 0.0439(13) 0.0329(11) 0.0302(11) 0.0111(9) 0.0096(9) 0.0138(10) C21 0.0448(14) 0.0391(13) 0.0425(13) 0.0113(10) 0.0133(11) 0.0059(10) C22 0.0481(14) 0.0477(14) 0.0445(13) 0.0200(11) 0.0210(11) 0.0103(11) C23 0.0452(13) 0.0427(13) 0.0308(11) 0.0182(10) 0.0158(10) 0.0186(11) C24 0.0423(12) 0.0448(13) 0.0316(11) 0.0177(10) 0.0147(10) 0.0207(10) C25 0.0477(13) 0.0430(13) 0.0336(12) 0.0175(10) 0.0136(10) 0.0178(11) C26 0.0655(17) 0.0714(18) 0.0478(14) 0.0313(13) 0.0233(13) 0.0400(14) C27 0.0603(17) 0.0714(19) 0.0624(17) 0.0296(15) 0.0160(14) 0.0367(15) C28 0.074(2) 0.086(2) 0.0602(18) 0.0396(16) 0.0066(15) 0.0427(17) C29 0.088(2) 0.128(3) 0.0454(16) 0.0501(18) 0.0199(15) 0.055(2) C30 0.0435(13) 0.0426(12) 0.0296(11) 0.0145(10) 0.0122(10) 0.0229(10) C31 0.0496(14) 0.0511(14) 0.0391(13) 0.0159(11) 0.0004(11) 0.0248(12) C32 0.0450(14) 0.0409(13) 0.0417(13) 0.0076(10) -0.0020(11) 0.0117(11) C33 0.0381(12) 0.0347(12) 0.0327(11) 0.0087(9) 0.0099(10) 0.0158(10) C34 0.0400(12) 0.0333(11) 0.0345(11) 0.0119(9) 0.0112(9) 0.0139(9) C35 0.0535(14) 0.0456(13) 0.0422(13) 0.0176(11) 0.0183(11) 0.0277(11) C36 0.0822(19) 0.0587(16) 0.0481(15) 0.0133(13) 0.0270(14) 0.0351(15) C37 0.0530(15) 0.0415(13) 0.0482(14) 0.0140(11) 0.0095(12) 0.0043(11) C38 0.088(2) 0.0581(18) 0.094(2) 0.0449(17) 0.0147(18) 0.0028(16) N1 0.0319(10) 0.0459(11) 0.0335(10) 0.0160(8) 0.0080(8) 0.0150(9) N2 0.0359(10) 0.0388(10) 0.0297(9) 0.0136(8) 0.0140(8) 0.0126(8) N3 0.0389(10) 0.0380(10) 0.0312(9) 0.0123(8) 0.0097(8) 0.0092(8) N4 0.0402(10) 0.0360(10) 0.0287(9) 0.0116(8) 0.0065(8) 0.0156(8) N5 0.0655(14) 0.0936(17) 0.0381(11) 0.0326(12) 0.0187(10) 0.0405(13) N6 0.0517(13) 0.0537(13) 0.0548(13) 0.0206(11) 0.0141(10) 0.0047(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 H1W 1.00(2) . ? O1 H2W 1.01(2) . ? C1 C2 1.364(3) . ? C1 N1 1.368(3) . ? C1 C34 1.512(3) . ? C2 C3 1.414(3) . ? C2 H026 0.9300 . ? C3 C4 1.359(3) . ? C3 H020 0.9300 . ? C4 N1 1.374(3) . ? C4 C5 1.500(3) . ? C5 C11 1.508(3) . ? C5 C6 1.520(3) . ? C5 H5 0.9800 . ? C6 N6 1.337(3) . ? C6 C7 1.384(3) . ? C7 C8 1.377(4) . ? C7 H44 0.9300 . ? C8 C9 1.352(4) . ? C8 H034 0.9300 . ? C9 C10 1.374(4) . ? C9 H038 0.9300 . ? C10 N6 1.337(3) . ? C10 H036 0.9300 . ? C11 C12 1.363(3) . ? C11 N2 1.375(3) . ? C12 C13 1.410(3) . ? C12 H018 0.9300 . ? C13 C14 1.365(3) . ? C13 H021 0.9300 . ? C14 N2 1.376(3) . ? C14 C15 1.518(3) . ? C15 C20 1.507(3) . ? C15 C18 1.553(3) . ? C15 C16 1.553(3) . ? C16 C17 1.523(3) . ? C16 H02C 0.9700 . ? C16 H02D 0.9700 . ? C17 H03C 0.9600 . ? C17 H03D 0.9600 . ? C17 H03E 0.9600 . ? C18 C19 1.519(4) . ? C18 H03A 0.9700 . ? C18 H03B 0.9700 . ? C19 H03F 0.9600 . ? C19 H03G 0.9600 . ? C19 H03H 0.9600 . ? C20 C21 1.369(3) . ? C20 N3 1.380(3) . ? C21 C22 1.414(3) . ? C21 H019 0.9300 . ? C22 C23 1.364(3) . ? C22 H024 0.9300 . ? C23 N3 1.376(3) . ? C23 C24 1.504(3) . ? C24 C30 1.515(3) . ? C24 C25 1.527(3) . ? C24 H24 0.9800 . ? C25 N5 1.326(3) . ? C25 C26 1.378(3) . ? C26 C27 1.377(3) . ? C26 H028 0.9300 . ? C27 C28 1.361(4) . ? C27 H031 0.9300 . ? C28 C29 1.367(4) . ? C28 H037 0.9300 . ? C29 N5 1.352(3) . ? C29 H032 0.9300 . ? C30 C31 1.367(3) . ? C30 N4 1.372(3) . ? C31 C32 1.408(3) . ? C31 H016 0.9300 . ? C32 C33 1.373(3) . ? C32 H027 0.9300 . ? C33 N4 1.381(3) . ? C33 C34 1.513(3) . ? C34 C37 1.550(3) . ? C34 C35 1.551(3) . ? C35 C36 1.522(3) . ? C35 H01A 0.9700 . ? C35 H01B 0.9700 . ? C36 H02E 0.9600 . ? C36 H02F 0.9600 . ? C36 H02G 0.9600 . ? C37 C38 1.529(4) . ? C37 H02A 0.9700 . ? C37 H02B 0.9700 . ? C38 H04A 0.9600 . ? C38 H04B 0.9600 . ? C38 H04C 0.9600 . ? N1 H1 0.856(15) . ? N2 H2 0.863(15) . ? N3 H3 0.862(15) . ? N4 H4 0.871(15) . ? 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 H1W O1 H2W 98(2) . . ? C2 C1 N1 106.28(19) . . ? C2 C1 C34 132.66(19) . . ? N1 C1 C34 121.04(18) . . ? C1 C2 C3 108.5(2) . . ? C1 C2 H026 125.7 . . ? C3 C2 H026 125.7 . . ? C4 C3 C2 107.54(19) . . ? C4 C3 H020 126.2 . . ? C2 C3 H020 126.2 . . ? C3 C4 N1 106.92(18) . . ? C3 C4 C5 131.36(19) . . ? N1 C4 C5 121.71(18) . . ? C4 C5 C11 114.13(17) . . ? C4 C5 C6 111.18(17) . . ? C11 C5 C6 109.99(18) . . ? C4 C5 H5 107.1 . . ? C11 C5 H5 107.1 . . ? C6 C5 H5 107.1 . . ? N6 C6 C7 122.2(2) . . ? N6 C6 C5 116.41(18) . . ? C7 C6 C5 121.4(2) . . ? C8 C7 C6 118.8(3) . . ? C8 C7 H44 120.6 . . ? C6 C7 H44 120.6 . . ? C9 C8 C7 119.5(3) . . ? C9 C8 H034 120.3 . . ? C7 C8 H034 120.3 . . ? C8 C9 C10 118.6(3) . . ? C8 C9 H038 120.7 . . ? C10 C9 H038 120.7 . . ? N6 C10 C9 123.5(3) . . ? N6 C10 H036 118.2 . . ? C9 C10 H036 118.2 . . ? C12 C11 N2 107.04(19) . . ? C12 C11 C5 130.02(19) . . ? N2 C11 C5 122.74(18) . . ? C11 C12 C13 107.76(19) . . ? C11 C12 H018 126.1 . . ? C13 C12 H018 126.1 . . ? C14 C13 C12 108.46(19) . . ? C14 C13 H021 125.8 . . ? C12 C13 H021 125.8 . . ? C13 C14 N2 106.46(18) . . ? C13 C14 C15 130.76(19) . . ? N2 C14 C15 122.51(17) . . ? C20 C15 C14 111.54(16) . . ? C20 C15 C18 108.50(17) . . ? C14 C15 C18 108.64(17) . . ? C20 C15 C16 108.17(17) . . ? C14 C15 C16 109.00(17) . . ? C18 C15 C16 111.00(18) . . ? C17 C16 C15 116.09(19) . . ? C17 C16 H02C 108.3 . . ? C15 C16 H02C 108.3 . . ? C17 C16 H02D 108.3 . . ? C15 C16 H02D 108.3 . . ? H02C C16 H02D 107.4 . . ? C16 C17 H03C 109.5 . . ? C16 C17 H03D 109.5 . . ? H03C C17 H03D 109.5 . . ? C16 C17 H03E 109.5 . . ? H03C C17 H03E 109.5 . . ? H03D C17 H03E 109.5 . . ? C19 C18 C15 115.3(2) . . ? C19 C18 H03A 108.4 . . ? C15 C18 H03A 108.4 . . ? C19 C18 H03B 108.4 . . ? C15 C18 H03B 108.4 . . ? H03A C18 H03B 107.5 . . ? C18 C19 H03F 109.5 . . ? C18 C19 H03G 109.5 . . ? H03F C19 H03G 109.5 . . ? C18 C19 H03H 109.5 . . ? H03F C19 H03H 109.5 . . ? H03G C19 H03H 109.5 . . ? C21 C20 N3 106.25(18) . . ? C21 C20 C15 131.93(19) . . ? N3 C20 C15 121.55(18) . . ? C20 C21 C22 108.38(19) . . ? C20 C21 H019 125.8 . . ? C22 C21 H019 125.8 . . ? C23 C22 C21 107.93(19) . . ? C23 C22 H024 126.0 . . ? C21 C22 H024 126.0 . . ? C22 C23 N3 106.90(18) . . ? C22 C23 C24 128.89(19) . . ? N3 C23 C24 124.18(19) . . ? C23 C24 C30 114.54(16) . . ? C23 C24 C25 113.18(17) . . ? C30 C24 C25 110.61(17) . . ? C23 C24 H24 105.9 . . ? C30 C24 H24 105.9 . . ? C25 C24 H24 105.9 . . ? N5 C25 C26 121.7(2) . . ? N5 C25 C24 115.50(19) . . ? C26 C25 C24 122.82(19) . . ? C27 C26 C25 120.0(2) . . ? C27 C26 H028 120.0 . . ? C25 C26 H028 120.0 . . ? C28 C27 C26 118.9(2) . . ? C28 C27 H031 120.5 . . ? C26 C27 H031 120.5 . . ? C27 C28 C29 118.1(2) . . ? C27 C28 H037 121.0 . . ? C29 C28 H037 121.0 . . ? N5 C29 C28 124.0(2) . . ? N5 C29 H032 118.0 . . ? C28 C29 H032 118.0 . . ? C31 C30 N4 106.76(19) . . ? C31 C30 C24 130.79(19) . . ? N4 C30 C24 121.94(18) . . ? C30 C31 C32 108.13(19) . . ? C30 C31 H016 125.9 . . ? C32 C31 H016 125.9 . . ? C33 C32 C31 108.3(2) . . ? C33 C32 H027 125.8 . . ? C31 C32 H027 125.8 . . ? C32 C33 N4 106.08(19) . . ? C32 C33 C34 131.84(19) . . ? N4 C33 C34 121.70(18) . . ? C1 C34 C33 110.60(16) . . ? C1 C34 C37 108.99(17) . . ? C33 C34 C37 109.11(18) . . ? C1 C34 C35 107.75(17) . . ? C33 C34 C35 109.28(17) . . ? C37 C34 C35 111.11(18) . . ? C36 C35 C34 116.18(19) . . ? C36 C35 H01A 108.2 . . ? C34 C35 H01A 108.2 . . ? C36 C35 H01B 108.2 . . ? C34 C35 H01B 108.2 . . ? H01A C35 H01B 107.4 . . ? C35 C36 H02E 109.5 . . ? C35 C36 H02F 109.5 . . ? H02E C36 H02F 109.5 . . ? C35 C36 H02G 109.5 . . ? H02E C36 H02G 109.5 . . ? H02F C36 H02G 109.5 . . ? C38 C37 C34 114.5(2) . . ? C38 C37 H02A 108.6 . . ? C34 C37 H02A 108.6 . . ? C38 C37 H02B 108.6 . . ? C34 C37 H02B 108.6 . . ? H02A C37 H02B 107.6 . . ? C37 C38 H04A 109.5 . . ? C37 C38 H04B 109.5 . . ? H04A C38 H04B 109.5 . . ? C37 C38 H04C 109.5 . . ? H04A C38 H04C 109.5 . . ? H04B C38 H04C 109.5 . . ? C1 N1 C4 110.73(17) . . ? C1 N1 H1 125.3(15) . . ? C4 N1 H1 122.8(15) . . ? C11 N2 C14 110.27(17) . . ? C11 N2 H2 124.8(14) . . ? C14 N2 H2 124.7(14) . . ? C23 N3 C20 110.54(17) . . ? C23 N3 H3 125.7(15) . . ? C20 N3 H3 123.8(15) . . ? C30 N4 C33 110.72(17) . . ? C30 N4 H4 122.6(15) . . ? C33 N4 H4 126.4(15) . . ? C25 N5 C29 117.3(2) . . ? C6 N6 C10 117.3(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -0.6(2) . . . . ? C34 C1 C2 C3 177.6(2) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C2 C3 C4 N1 0.9(2) . . . . ? C2 C3 C4 C5 -178.3(2) . . . . ? C3 C4 C5 C11 -120.3(3) . . . . ? N1 C4 C5 C11 60.6(3) . . . . ? C3 C4 C5 C6 114.6(3) . . . . ? N1 C4 C5 C6 -64.5(3) . . . . ? C4 C5 C6 N6 57.8(3) . . . . ? C11 C5 C6 N6 -69.6(2) . . . . ? C4 C5 C6 C7 -122.8(2) . . . . ? C11 C5 C6 C7 109.7(2) . . . . ? N6 C6 C7 C8 -1.0(4) . . . . ? C5 C6 C7 C8 179.7(2) . . . . ? C6 C7 C8 C9 -0.1(4) . . . . ? C7 C8 C9 C10 0.8(5) . . . . ? C8 C9 C10 N6 -0.7(5) . . . . ? C4 C5 C11 C12 -149.8(2) . . . . ? C6 C5 C11 C12 -24.1(3) . . . . ? C4 C5 C11 N2 35.8(3) . . . . ? C6 C5 C11 N2 161.58(18) . . . . ? N2 C11 C12 C13 -0.3(2) . . . . ? C5 C11 C12 C13 -175.3(2) . . . . ? C11 C12 C13 C14 0.1(3) . . . . ? C12 C13 C14 N2 0.1(2) . . . . ? C12 C13 C14 C15 174.1(2) . . . . ? C13 C14 C15 C20 152.5(2) . . . . ? N2 C14 C15 C20 -34.3(3) . . . . ? C13 C14 C15 C18 32.9(3) . . . . ? N2 C14 C15 C18 -153.89(18) . . . . ? C13 C14 C15 C16 -88.1(3) . . . . ? N2 C14 C15 C16 85.0(2) . . . . ? C20 C15 C16 C17 -172.69(19) . . . . ? C14 C15 C16 C17 65.9(2) . . . . ? C18 C15 C16 C17 -53.8(3) . . . . ? C20 C15 C18 C19 57.9(3) . . . . ? C14 C15 C18 C19 179.3(2) . . . . ? C16 C15 C18 C19 -60.9(3) . . . . ? C14 C15 C20 C21 131.5(2) . . . . ? C18 C15 C20 C21 -108.9(3) . . . . ? C16 C15 C20 C21 11.6(3) . . . . ? C14 C15 C20 N3 -55.3(3) . . . . ? C18 C15 C20 N3 64.3(2) . . . . ? C16 C15 C20 N3 -175.18(18) . . . . ? N3 C20 C21 C22 0.2(2) . . . . ? C15 C20 C21 C22 174.1(2) . . . . ? C20 C21 C22 C23 -0.1(3) . . . . ? C21 C22 C23 N3 0.1(3) . . . . ? C21 C22 C23 C24 -177.9(2) . . . . ? C22 C23 C24 C30 -134.7(2) . . . . ? N3 C23 C24 C30 47.6(3) . . . . ? C22 C23 C24 C25 97.3(3) . . . . ? N3 C23 C24 C25 -80.4(2) . . . . ? C23 C24 C25 N5 -134.4(2) . . . . ? C30 C24 C25 N5 95.5(2) . . . . ? C23 C24 C25 C26 45.3(3) . . . . ? C30 C24 C25 C26 -84.8(3) . . . . ? N5 C25 C26 C27 -0.5(4) . . . . ? C24 C25 C26 C27 179.9(2) . . . . ? C25 C26 C27 C28 0.7(4) . . . . ? C26 C27 C28 C29 -0.3(4) . . . . ? C27 C28 C29 N5 -0.3(5) . . . . ? C23 C24 C30 C31 -146.4(2) . . . . ? C25 C24 C30 C31 -17.1(3) . . . . ? C23 C24 C30 N4 42.9(3) . . . . ? C25 C24 C30 N4 172.23(18) . . . . ? N4 C30 C31 C32 -0.3(2) . . . . ? C24 C30 C31 C32 -172.0(2) . . . . ? C30 C31 C32 C33 0.3(3) . . . . ? C31 C32 C33 N4 -0.1(2) . . . . ? C31 C32 C33 C34 172.7(2) . . . . ? C2 C1 C34 C33 121.0(3) . . . . ? N1 C1 C34 C33 -61.1(2) . . . . ? C2 C1 C34 C37 -119.1(3) . . . . ? N1 C1 C34 C37 58.9(2) . . . . ? C2 C1 C34 C35 1.6(3) . . . . ? N1 C1 C34 C35 179.54(18) . . . . ? C32 C33 C34 C1 153.7(2) . . . . ? N4 C33 C34 C1 -34.3(3) . . . . ? C32 C33 C34 C37 33.9(3) . . . . ? N4 C33 C34 C37 -154.20(19) . . . . ? C32 C33 C34 C35 -87.8(3) . . . . ? N4 C33 C34 C35 84.1(2) . . . . ? C1 C34 C35 C36 -174.20(19) . . . . ? C33 C34 C35 C36 65.6(2) . . . . ? C37 C34 C35 C36 -54.9(3) . . . . ? C1 C34 C37 C38 58.3(3) . . . . ? C33 C34 C37 C38 179.2(2) . . . . ? C35 C34 C37 C38 -60.3(3) . . . . ? C2 C1 N1 C4 1.2(2) . . . . ? C34 C1 N1 C4 -177.24(18) . . . . ? C3 C4 N1 C1 -1.3(2) . . . . ? C5 C4 N1 C1 178.00(18) . . . . ? C12 C11 N2 C14 0.4(2) . . . . ? C5 C11 N2 C14 175.84(18) . . . . ? C13 C14 N2 C11 -0.3(2) . . . . ? C15 C14 N2 C11 -174.93(17) . . . . ? C22 C23 N3 C20 0.0(2) . . . . ? C24 C23 N3 C20 178.15(18) . . . . ? C21 C20 N3 C23 -0.1(2) . . . . ? C15 C20 N3 C23 -174.87(18) . . . . ? C31 C30 N4 C33 0.2(2) . . . . ? C24 C30 N4 C33 172.88(17) . . . . ? C32 C33 N4 C30 -0.1(2) . . . . ? C34 C33 N4 C30 -173.82(18) . . . . ? C26 C25 N5 C29 -0.1(4) . . . . ? C24 C25 N5 C29 179.6(2) . . . . ? C28 C29 N5 C25 0.5(5) . . . . ? C7 C6 N6 C10 1.2(4) . . . . ? C5 C6 N6 C10 -179.5(2) . . . . ? C9 C10 N6 C6 -0.3(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1W N5 1.00(2) 1.91(2) 2.910(3) 174(2) . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.174 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.039 data_antiiso _database_code_depnum_ccdc_archive 'CCDC 896705' #TrackingRef 'antiiso.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H43.33 N6 O0.66' _chemical_formula_weight 594.68 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.774(2) _cell_length_b 13.988(3) _cell_length_c 17.936(3) _cell_angle_alpha 97.519(6) _cell_angle_beta 104.854(6) _cell_angle_gamma 111.281(5) _cell_volume 2577.1(8) _cell_formula_units_Z 3 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 31096 _cell_measurement_theta_min 1.76 _cell_measurement_theta_max 25.00 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.150 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 956 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9792 _exptl_absorpt_correction_T_max 0.9944 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-APEX-II CCD area detector' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31096 _diffrn_reflns_av_R_equivalents 0.0614 _diffrn_reflns_av_sigmaI/netI 0.0693 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.00 _reflns_number_total 9037 _reflns_number_gt 4643 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0631P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9037 _refine_ls_number_parameters 628 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1194 _refine_ls_R_factor_gt 0.0530 _refine_ls_wR_factor_ref 0.1475 _refine_ls_wR_factor_gt 0.1182 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 C1 C 0.6684(2) 0.33175(19) 0.51031(14) 0.0496(6) Uani 1 1 d . . . C2 C 0.5488(3) 0.2658(2) 0.50555(19) 0.0776(9) Uani 1 1 d . . . H2 H 0.4878 0.2864 0.5181 0.093 Uiso 1 1 calc R . . C3 C 0.5311(3) 0.1601(2) 0.47845(18) 0.0789(9) Uani 1 1 d . . . H3 H 0.4566 0.0996 0.4695 0.095 Uiso 1 1 calc R . . C4 C 0.6417(2) 0.16263(19) 0.46789(14) 0.0533(7) Uani 1 1 d . . . C5 C 0.6788(2) 0.07376(18) 0.44575(15) 0.0580(7) Uani 1 1 d . . . H5 H 0.5986 0.0090 0.4264 0.070 Uiso 1 1 calc R . . C6 C 0.7351(3) 0.0806(2) 0.37853(15) 0.0580(7) Uani 1 1 d . . . C7 C 0.6832(3) -0.0021(2) 0.31191(18) 0.0800(9) Uani 1 1 d . . . H7 H 0.6112 -0.0628 0.3068 0.096 Uiso 1 1 calc R . . C8 C 0.7386(4) 0.0057(3) 0.2530(2) 0.0962(11) Uani 1 1 d . . . H8 H 0.7050 -0.0497 0.2077 0.115 Uiso 1 1 calc R . . C9 C 0.8430(4) 0.0952(3) 0.26189(19) 0.0879(10) Uani 1 1 d . . . H9 H 0.8822 0.1025 0.2228 0.106 Uiso 1 1 calc R . . C10 C 0.8895(3) 0.1747(2) 0.3295(2) 0.0821(9) Uani 1 1 d . . . H10 H 0.9609 0.2361 0.3350 0.099 Uiso 1 1 calc R . . C11 C 0.7659(2) 0.05839(17) 0.51643(15) 0.0523(7) Uani 1 1 d . . . C12 C 0.8513(3) 0.01298(19) 0.52164(16) 0.0642(8) Uani 1 1 d . . . H12 H 0.8750 -0.0114 0.4799 0.077 Uiso 1 1 calc R . . C13 C 0.8975(3) 0.00948(19) 0.60142(17) 0.0641(7) Uani 1 1 d . . . H13 H 0.9569 -0.0179 0.6212 0.077 Uiso 1 1 calc R . . C14 C 0.8406(2) 0.05291(18) 0.64481(15) 0.0525(6) Uani 1 1 d . . . C15 C 0.8474(2) 0.06775(19) 0.73114(15) 0.0569(7) Uani 1 1 d . . . C16 C 0.7261(3) -0.0192(2) 0.73760(17) 0.0769(9) Uani 1 1 d . . . H16A H 0.7271 -0.0052 0.7922 0.092 Uiso 1 1 calc R . . H16B H 0.6502 -0.0142 0.7044 0.092 Uiso 1 1 calc R . . C17 C 0.7137(4) -0.1324(2) 0.7132(2) 0.1057(12) Uani 1 1 d . . . H17A H 0.6363 -0.1810 0.7191 0.159 Uiso 1 1 calc R . . H17B H 0.7871 -0.1391 0.7466 0.159 Uiso 1 1 calc R . . H17C H 0.7098 -0.1482 0.6587 0.159 Uiso 1 1 calc R . . C18 C 0.9726(3) 0.0620(2) 0.78010(16) 0.0759(9) Uani 1 1 d . . . H18A H 0.9705 -0.0065 0.7591 0.091 Uiso 1 1 calc R . . H18B H 1.0454 0.1157 0.7723 0.091 Uiso 1 1 calc R . . C19 C 0.9955(4) 0.0771(3) 0.86943(19) 0.1191(14) Uani 1 1 d . . . H19A H 1.0754 0.0731 0.8949 0.179 Uiso 1 1 calc R . . H19B H 0.9259 0.0226 0.8782 0.179 Uiso 1 1 calc R . . H19C H 0.9996 0.1452 0.8913 0.179 Uiso 1 1 calc R . . C20 C 0.8488(2) 0.17480(19) 0.75989(14) 0.0520(6) Uani 1 1 d . . . C21 C 0.7611(3) 0.2052(2) 0.78063(15) 0.0623(7) Uani 1 1 d . . . H21 H 0.6815 0.1601 0.7821 0.075 Uiso 1 1 calc R . . C22 C 0.8118(3) 0.3171(2) 0.79955(15) 0.0617(7) Uani 1 1 d . . . H22 H 0.7715 0.3585 0.8152 0.074 Uiso 1 1 calc R . . C23 C 0.9309(2) 0.35326(18) 0.79062(14) 0.0503(6) Uani 1 1 d . . . C24 C 1.0259(2) 0.46239(18) 0.79469(14) 0.0519(7) Uani 1 1 d . . . H24 H 1.1113 0.4612 0.8069 0.062 Uiso 1 1 calc R . . C25 C 1.0323(3) 0.54401(19) 0.86216(17) 0.0601(7) Uani 1 1 d . . . C26 C 0.9589(4) 0.6003(3) 0.8523(2) 0.1147(13) Uani 1 1 d . . . H26 H 0.9041 0.5920 0.8020 0.138 Uiso 1 1 calc R . . C27 C 0.9664(5) 0.6705(3) 0.9180(3) 0.1383(17) Uani 1 1 d . . . H27 H 0.9152 0.7082 0.9126 0.166 Uiso 1 1 calc R . . C28 C 1.0498(4) 0.6824(3) 0.9899(3) 0.1149(13) Uani 1 1 d . . . H28 H 1.0576 0.7290 1.0349 0.138 Uiso 1 1 calc R . . C29 C 1.1210(3) 0.6257(3) 0.99512(19) 0.0921(10) Uani 1 1 d . . . H29 H 1.1792 0.6356 1.0446 0.111 Uiso 1 1 calc R . . C30 C 0.9958(2) 0.48830(19) 0.71556(15) 0.0503(6) Uani 1 1 d . . . C31 C 1.0698(3) 0.5546(2) 0.68105(17) 0.0668(8) Uani 1 1 d . . . H31 H 1.1583 0.5951 0.7025 0.080 Uiso 1 1 calc R . . C32 C 0.9879(3) 0.5510(2) 0.60639(17) 0.0633(7) Uani 1 1 d . . . H32 H 1.0136 0.5889 0.5703 0.076 Uiso 1 1 calc R . . C33 C 0.8663(2) 0.48320(18) 0.59669(15) 0.0483(6) Uani 1 1 d . . . C34 C 0.7383(2) 0.45036(18) 0.53306(15) 0.0513(6) Uani 1 1 d . . . C35 C 0.6559(3) 0.4969(2) 0.56776(17) 0.0682(8) Uani 1 1 d . . . H35A H 0.5732 0.4755 0.5268 0.082 Uiso 1 1 calc R . . H35B H 0.6396 0.4658 0.6113 0.082 Uiso 1 1 calc R . . C36 C 0.7156(3) 0.6165(2) 0.5979(2) 0.1033(11) Uani 1 1 d . . . H36A H 0.6585 0.6380 0.6184 0.155 Uiso 1 1 calc R . . H36B H 0.7296 0.6484 0.5550 0.155 Uiso 1 1 calc R . . H36C H 0.7966 0.6388 0.6395 0.155 Uiso 1 1 calc R . . C37 C 0.7608(3) 0.4909(2) 0.46026(16) 0.0656(8) Uani 1 1 d . . . H37A H 0.8043 0.5676 0.4765 0.079 Uiso 1 1 calc R . . H37B H 0.8186 0.4650 0.4435 0.079 Uiso 1 1 calc R . . C38 C 0.6399(3) 0.4596(3) 0.38852(18) 0.0914(10) Uani 1 1 d . . . H38A H 0.6639 0.4886 0.3464 0.137 Uiso 1 1 calc R . . H38B H 0.5827 0.4866 0.4036 0.137 Uiso 1 1 calc R . . H38C H 0.5971 0.3838 0.3705 0.137 Uiso 1 1 calc R . . C39 C 0.1069(3) 0.2616(2) 0.62523(18) 0.0685(8) Uani 1 1 d . . . H39 H 0.0217 0.2527 0.6051 0.082 Uiso 1 1 calc R . . C40 C 0.1621(4) 0.2322(2) 0.57324(18) 0.0765(9) Uani 1 1 d . . . H40 H 0.1160 0.2045 0.5191 0.092 Uiso 1 1 calc R . . C41 C 0.2864(4) 0.2445(2) 0.6029(2) 0.0796(9) Uani 1 1 d . . . H41 H 0.3261 0.2232 0.5694 0.096 Uiso 1 1 calc R . . C42 C 0.3535(3) 0.2887(2) 0.68321(18) 0.0709(8) Uani 1 1 d . . . H42 H 0.4392 0.2990 0.7039 0.085 Uiso 1 1 calc R . . C43 C 0.2920(3) 0.31754(18) 0.73268(15) 0.0514(6) Uani 1 1 d . . . C44 C 0.3574(2) 0.37084(18) 0.82074(14) 0.0497(6) Uani 1 1 d . . . H44 H 0.2887 0.3750 0.8405 0.060 Uiso 1 1 calc R . . C45 C 0.4514(2) 0.48469(19) 0.83458(15) 0.0519(6) Uani 1 1 d . . . C46 C 0.5512(3) 0.5313(2) 0.80785(17) 0.0706(8) Uani 1 1 d . . . H46 H 0.5793 0.4968 0.7735 0.085 Uiso 1 1 calc R . . C47 C 0.6046(3) 0.6419(2) 0.84168(17) 0.0712(8) Uani 1 1 d . . . H47 H 0.6744 0.6926 0.8336 0.085 Uiso 1 1 calc R . . C48 C 0.5367(2) 0.66085(19) 0.88774(16) 0.0554(7) Uani 1 1 d . . . C49 C 0.5433(2) 0.76132(19) 0.93647(16) 0.0603(7) Uani 1 1 d . . . C50 C 0.4262(3) 0.7829(2) 0.89343(18) 0.0801(9) Uani 1 1 d . . . H50A H 0.3476 0.7235 0.8892 0.096 Uiso 1 1 calc R . . H50B H 0.4288 0.8452 0.9261 0.096 Uiso 1 1 calc R . . C51 C 0.4197(3) 0.7999(3) 0.8107(2) 0.1096(12) Uani 1 1 d . . . H51A H 0.3447 0.8124 0.7884 0.164 Uiso 1 1 calc R . . H51B H 0.4148 0.7380 0.7773 0.164 Uiso 1 1 calc R . . H51C H 0.4957 0.8600 0.8143 0.164 Uiso 1 1 calc R . . C52 C 0.6721(3) 0.8547(2) 0.94602(17) 0.0765(9) Uani 1 1 d . . . H52A H 0.7427 0.8381 0.9729 0.092 Uiso 1 1 calc R . . H52B H 0.6767 0.8597 0.8934 0.092 Uiso 1 1 calc R . . C53 C 0.6928(4) 0.9626(2) 0.9916(2) 0.1137(13) Uani 1 1 d . . . H53A H 0.7745 1.0148 0.9939 0.171 Uiso 1 1 calc R . . H53B H 0.6919 0.9600 1.0447 0.171 Uiso 1 1 calc R . . H53C H 0.6250 0.9813 0.9650 0.171 Uiso 1 1 calc R . . C54 C 0.5374(3) 0.74598(19) 1.01741(17) 0.0581(7) Uani 1 1 d . . . C55 C 0.4737(3) 0.7712(2) 1.06485(19) 0.0734(8) Uani 1 1 d . . . H55 H 0.4200 0.8062 1.0532 0.088 Uiso 1 1 calc R . . C56 C 0.5023(3) 0.7358(2) 1.13462(18) 0.0701(8) Uani 1 1 d . . . H56 H 0.4708 0.7429 1.1766 0.084 Uiso 1 1 calc R . . C57 C 0.5844(2) 0.68956(18) 1.12940(16) 0.0524(6) Uani 1 1 d . . . N1 N 0.72518(19) 0.26758(16) 0.48798(12) 0.0531(6) Uani 1 1 d . . . H1 H 0.801(2) 0.2906(19) 0.4821(14) 0.064 Uiso 1 1 d . . . N2 N 0.7600(2) 0.08237(15) 0.59132(13) 0.0527(6) Uani 1 1 d . . . H4 H 0.714(2) 0.1139(18) 0.6053(14) 0.063 Uiso 1 1 d . . . N3 N 0.9522(2) 0.26601(16) 0.76657(11) 0.0508(5) Uani 1 1 d . . . H6 H 1.022(2) 0.2731(18) 0.7495(14) 0.061 Uiso 1 1 d . . . N4 N 0.8721(2) 0.44594(16) 0.66376(13) 0.0516(6) Uani 1 1 d . . . H11 H 0.807(2) 0.3983(19) 0.6742(14) 0.062 Uiso 1 1 d . . . N5 N 0.8381(2) 0.16936(17) 0.38860(14) 0.0692(6) Uani 1 1 d . . . N6 N 1.1132(2) 0.55582(17) 0.93329(14) 0.0701(6) Uani 1 1 d . . . N7 N 0.1685(2) 0.30251(15) 0.70380(13) 0.0566(6) Uani 1 1 d . . . N8 N 0.4434(2) 0.56424(16) 0.88294(13) 0.0548(6) Uani 1 1 d . . . H14 H 0.396(2) 0.5541(19) 0.9151(15) 0.066 Uiso 1 1 d . . . N9 N 0.6064(2) 0.69765(16) 1.05869(13) 0.0551(6) Uani 1 1 d . . . H15 H 0.643(2) 0.6626(19) 1.0385(15) 0.066 Uiso 1 1 d . . . O1 O 1.2890(2) 0.46233(19) 0.98512(14) 0.0948(8) Uani 1 1 d . . . H1W H 1.224(3) 0.484(3) 0.9647(19) 0.114 Uiso 1 1 d . . . H2W H 1.303(3) 0.480(3) 1.037(2) 0.114 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0410(15) 0.0572(16) 0.0542(16) 0.0165(12) 0.0153(12) 0.0234(13) C2 0.0502(18) 0.080(2) 0.114(3) 0.0348(18) 0.0375(17) 0.0289(17) C3 0.0462(18) 0.067(2) 0.107(3) 0.0269(17) 0.0193(17) 0.0077(15) C4 0.0431(16) 0.0497(16) 0.0533(17) 0.0136(12) 0.0080(13) 0.0093(13) C5 0.0568(17) 0.0415(14) 0.0553(18) 0.0108(12) 0.0072(14) 0.0063(13) C6 0.0685(18) 0.0465(16) 0.0516(18) 0.0124(13) 0.0129(15) 0.0204(14) C7 0.100(2) 0.0630(19) 0.058(2) 0.0029(16) 0.0147(19) 0.0246(17) C8 0.133(3) 0.079(3) 0.068(2) 0.0027(19) 0.026(2) 0.045(2) C9 0.126(3) 0.098(3) 0.074(2) 0.028(2) 0.046(2) 0.072(3) C10 0.093(2) 0.071(2) 0.095(3) 0.029(2) 0.045(2) 0.0372(18) C11 0.0616(17) 0.0366(13) 0.0470(17) 0.0054(11) 0.0125(14) 0.0128(13) C12 0.084(2) 0.0563(16) 0.0547(19) 0.0080(13) 0.0236(16) 0.0337(16) C13 0.081(2) 0.0590(17) 0.061(2) 0.0132(14) 0.0222(16) 0.0399(16) C14 0.0587(16) 0.0418(14) 0.0512(17) 0.0101(12) 0.0111(14) 0.0198(13) C15 0.0654(18) 0.0494(15) 0.0558(18) 0.0137(13) 0.0183(14) 0.0244(14) C16 0.096(2) 0.0580(18) 0.075(2) 0.0222(15) 0.0349(18) 0.0233(17) C17 0.142(3) 0.056(2) 0.117(3) 0.0289(19) 0.053(2) 0.029(2) C18 0.095(2) 0.078(2) 0.062(2) 0.0164(15) 0.0124(17) 0.0532(18) C19 0.163(4) 0.154(3) 0.061(2) 0.024(2) 0.014(2) 0.104(3) C20 0.0558(17) 0.0504(16) 0.0463(16) 0.0098(12) 0.0150(13) 0.0202(14) C21 0.0609(18) 0.0613(18) 0.0670(19) 0.0132(14) 0.0286(15) 0.0237(15) C22 0.0620(18) 0.0637(18) 0.0675(19) 0.0121(14) 0.0289(15) 0.0313(15) C23 0.0551(17) 0.0479(15) 0.0451(16) 0.0045(12) 0.0122(13) 0.0236(13) C24 0.0451(15) 0.0520(15) 0.0490(16) 0.0004(12) 0.0048(12) 0.0211(13) C25 0.0551(17) 0.0569(16) 0.0567(19) 0.0001(13) 0.0095(15) 0.0211(14) C26 0.136(3) 0.123(3) 0.087(3) -0.016(2) -0.005(2) 0.098(3) C27 0.166(4) 0.152(4) 0.109(3) -0.020(3) 0.012(3) 0.119(3) C28 0.120(3) 0.104(3) 0.105(3) -0.026(2) 0.026(3) 0.054(3) C29 0.089(2) 0.096(2) 0.065(2) -0.0110(18) 0.0133(18) 0.028(2) C30 0.0419(16) 0.0460(14) 0.0540(17) 0.0054(12) 0.0080(14) 0.0159(12) C31 0.0419(16) 0.0668(18) 0.076(2) 0.0146(15) 0.0123(16) 0.0110(14) C32 0.0549(18) 0.0645(18) 0.071(2) 0.0285(15) 0.0259(16) 0.0181(15) C33 0.0463(16) 0.0455(14) 0.0562(18) 0.0154(13) 0.0183(13) 0.0204(13) C34 0.0485(15) 0.0543(16) 0.0566(17) 0.0178(13) 0.0182(13) 0.0253(13) C35 0.0603(18) 0.0767(19) 0.077(2) 0.0176(15) 0.0194(15) 0.0412(16) C36 0.103(3) 0.086(2) 0.135(3) 0.011(2) 0.042(2) 0.059(2) C37 0.0728(19) 0.0653(17) 0.070(2) 0.0295(15) 0.0265(17) 0.0349(15) C38 0.096(2) 0.110(3) 0.071(2) 0.0421(19) 0.0177(19) 0.046(2) C39 0.0644(19) 0.0634(18) 0.058(2) 0.0061(15) 0.0071(16) 0.0170(15) C40 0.100(3) 0.0598(18) 0.055(2) 0.0070(14) 0.029(2) 0.0179(18) C41 0.100(3) 0.069(2) 0.073(2) 0.0080(17) 0.054(2) 0.0243(19) C42 0.0625(19) 0.0733(19) 0.075(2) 0.0090(16) 0.0321(17) 0.0235(16) C43 0.0543(17) 0.0439(14) 0.0553(17) 0.0123(12) 0.0229(14) 0.0163(13) C44 0.0472(15) 0.0509(15) 0.0493(16) 0.0116(12) 0.0148(12) 0.0194(12) C45 0.0518(16) 0.0518(16) 0.0512(16) 0.0142(13) 0.0135(13) 0.0224(13) C46 0.068(2) 0.067(2) 0.078(2) 0.0198(16) 0.0334(17) 0.0223(16) C47 0.0642(19) 0.063(2) 0.082(2) 0.0267(16) 0.0281(17) 0.0163(16) C48 0.0509(16) 0.0435(15) 0.0593(18) 0.0209(13) 0.0055(14) 0.0118(13) C49 0.0584(17) 0.0470(15) 0.0661(19) 0.0226(13) 0.0084(15) 0.0167(13) C50 0.089(2) 0.0655(19) 0.084(2) 0.0258(16) 0.0079(18) 0.0413(17) C51 0.112(3) 0.110(3) 0.096(3) 0.043(2) -0.003(2) 0.054(2) C52 0.079(2) 0.0564(18) 0.073(2) 0.0226(15) 0.0107(16) 0.0118(16) C53 0.128(3) 0.052(2) 0.121(3) 0.0104(19) 0.023(2) 0.0109(19) C54 0.0573(17) 0.0469(15) 0.069(2) 0.0179(14) 0.0136(15) 0.0235(14) C55 0.075(2) 0.0681(19) 0.088(2) 0.0242(17) 0.0221(18) 0.0435(17) C56 0.081(2) 0.0727(19) 0.075(2) 0.0232(16) 0.0352(17) 0.0437(17) C57 0.0495(16) 0.0473(15) 0.0572(18) 0.0106(13) 0.0162(14) 0.0184(13) N1 0.0402(12) 0.0475(13) 0.0627(15) 0.0107(10) 0.0142(11) 0.0113(11) N2 0.0554(14) 0.0463(12) 0.0549(15) 0.0102(10) 0.0162(11) 0.0215(10) N3 0.0507(14) 0.0524(13) 0.0501(13) 0.0063(10) 0.0174(11) 0.0238(12) N4 0.0414(14) 0.0515(13) 0.0585(15) 0.0175(11) 0.0161(12) 0.0145(11) N5 0.0739(17) 0.0553(15) 0.0726(17) 0.0136(12) 0.0313(14) 0.0162(13) N6 0.0698(16) 0.0690(15) 0.0546(16) -0.0027(12) 0.0125(13) 0.0218(13) N7 0.0529(14) 0.0581(13) 0.0512(15) 0.0083(11) 0.0135(12) 0.0189(11) N8 0.0546(14) 0.0498(13) 0.0597(15) 0.0162(11) 0.0203(11) 0.0192(12) N9 0.0556(14) 0.0574(14) 0.0583(16) 0.0199(11) 0.0179(12) 0.0285(11) O1 0.0998(18) 0.1228(19) 0.0819(16) 0.0226(15) 0.0342(15) 0.0663(15) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.348(3) . ? C1 N1 1.375(3) . ? C1 C34 1.502(3) . ? C2 C3 1.415(4) . ? C2 H2 0.9300 . ? C3 C4 1.352(3) . ? C3 H3 0.9300 . ? C4 N1 1.372(3) . ? C4 C5 1.499(3) . ? C5 C11 1.507(3) . ? C5 C6 1.515(3) . ? C5 H5 0.9800 . ? C6 N5 1.335(3) . ? C6 C7 1.375(3) . ? C7 C8 1.373(4) . ? C7 H7 0.9300 . ? C8 C9 1.354(4) . ? C8 H8 0.9300 . ? C9 C10 1.368(4) . ? C9 H9 0.9300 . ? C10 N5 1.346(3) . ? C10 H10 0.9300 . ? C11 C12 1.362(3) . ? C11 N2 1.367(3) . ? C12 C13 1.409(3) . ? C12 H12 0.9300 . ? C13 C14 1.364(3) . ? C13 H13 0.9300 . ? C14 N2 1.383(3) . ? C14 C15 1.512(3) . ? C15 C20 1.511(3) . ? C15 C16 1.547(3) . ? C15 C18 1.547(3) . ? C16 C17 1.529(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.527(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.364(3) . ? C20 N3 1.372(3) . ? C21 C22 1.414(3) . ? C21 H21 0.9300 . ? C22 C23 1.367(3) . ? C22 H22 0.9300 . ? C23 N3 1.370(3) . ? C23 C24 1.508(3) . ? C24 C30 1.497(3) . ? C24 C25 1.517(3) . ? C24 H24 0.9800 . ? C25 N6 1.330(3) . ? C25 C26 1.359(4) . ? C26 C27 1.394(4) . ? C26 H26 0.9300 . ? C27 C28 1.353(5) . ? C27 H27 0.9300 . ? C28 C29 1.342(4) . ? C28 H28 0.9300 . ? C29 N6 1.339(3) . ? C29 H29 0.9300 . ? C30 C31 1.357(3) . ? C30 N4 1.368(3) . ? C31 C32 1.418(4) . ? C31 H31 0.9300 . ? C32 C33 1.351(3) . ? C32 H32 0.9300 . ? C33 N4 1.368(3) . ? C33 C34 1.504(3) . ? C34 C37 1.536(3) . ? C34 C35 1.553(3) . ? C35 C36 1.517(4) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 C38 1.528(4) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? C39 N7 1.343(3) . ? C39 C40 1.365(4) . ? C39 H39 0.9300 . ? C40 C41 1.360(4) . ? C40 H40 0.9300 . ? C41 C42 1.381(4) . ? C41 H41 0.9300 . ? C42 C43 1.387(3) . ? C42 H42 0.9300 . ? C43 N7 1.337(3) . ? C43 C44 1.515(3) . ? C44 C57 1.512(3) 2_667 ? C44 C45 1.516(3) . ? C44 H44 0.9800 . ? C45 C46 1.360(3) . ? C45 N8 1.365(3) . ? C46 C47 1.417(4) . ? C46 H46 0.9300 . ? C47 C48 1.352(3) . ? C47 H47 0.9300 . ? C48 N8 1.372(3) . ? C48 C49 1.520(4) . ? C49 C54 1.510(4) . ? C49 C50 1.551(4) . ? C49 C52 1.551(4) . ? C50 C51 1.520(4) . ? C50 H50A 0.9700 . ? C50 H50B 0.9700 . ? C51 H51A 0.9600 . ? C51 H51B 0.9600 . ? C51 H51C 0.9600 . ? C52 C53 1.521(4) . ? C52 H52A 0.9700 . ? C52 H52B 0.9700 . ? C53 H53A 0.9600 . ? C53 H53B 0.9600 . ? C53 H53C 0.9600 . ? C54 C55 1.361(4) . ? C54 N9 1.373(3) . ? C55 C56 1.412(4) . ? C55 H55 0.9300 . ? C56 C57 1.359(3) . ? C56 H56 0.9300 . ? C57 N9 1.368(3) . ? C57 C44 1.512(3) 2_667 ? N1 H1 0.87(2) . ? N2 H4 0.87(2) . ? N3 H6 0.93(2) . ? N4 H11 0.90(2) . ? N8 H14 0.89(2) . ? N9 H15 0.86(2) . ? O1 H1W 0.93(3) . ? O1 H2W 0.88(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 N1 105.7(2) . . ? C2 C1 C34 132.5(2) . . ? N1 C1 C34 121.8(2) . . ? C1 C2 C3 108.9(2) . . ? C1 C2 H2 125.5 . . ? C3 C2 H2 125.5 . . ? C4 C3 C2 107.9(2) . . ? C4 C3 H3 126.0 . . ? C2 C3 H3 126.0 . . ? C3 C4 N1 106.2(2) . . ? C3 C4 C5 130.1(2) . . ? N1 C4 C5 123.5(2) . . ? C4 C5 C11 112.5(2) . . ? C4 C5 C6 114.5(2) . . ? C11 C5 C6 110.5(2) . . ? C4 C5 H5 106.2 . . ? C11 C5 H5 106.2 . . ? C6 C5 H5 106.2 . . ? N5 C6 C7 122.6(3) . . ? N5 C6 C5 116.5(2) . . ? C7 C6 C5 120.9(3) . . ? C8 C7 C6 119.4(3) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C9 C8 C7 119.0(3) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C8 C9 C10 118.7(3) . . ? C8 C9 H9 120.7 . . ? C10 C9 H9 120.7 . . ? N5 C10 C9 123.9(3) . . ? N5 C10 H10 118.1 . . ? C9 C10 H10 118.1 . . ? C12 C11 N2 106.6(2) . . ? C12 C11 C5 131.4(2) . . ? N2 C11 C5 121.7(2) . . ? C11 C12 C13 108.0(2) . . ? C11 C12 H12 126.0 . . ? C13 C12 H12 126.0 . . ? C14 C13 C12 108.7(2) . . ? C14 C13 H13 125.6 . . ? C12 C13 H13 125.6 . . ? C13 C14 N2 105.6(2) . . ? C13 C14 C15 133.3(2) . . ? N2 C14 C15 121.0(2) . . ? C20 C15 C14 108.7(2) . . ? C20 C15 C16 108.8(2) . . ? C14 C15 C16 109.0(2) . . ? C20 C15 C18 110.3(2) . . ? C14 C15 C18 108.5(2) . . ? C16 C15 C18 111.5(2) . . ? C17 C16 C15 115.0(3) . . ? C17 C16 H16A 108.5 . . ? C15 C16 H16A 108.5 . . ? C17 C16 H16B 108.5 . . ? C15 C16 H16B 108.5 . . ? H16A C16 H16B 107.5 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C15 115.2(2) . . ? C19 C18 H18A 108.5 . . ? C15 C18 H18A 108.5 . . ? C19 C18 H18B 108.5 . . ? C15 C18 H18B 108.5 . . ? H18A C18 H18B 107.5 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 N3 106.5(2) . . ? C21 C20 C15 132.9(2) . . ? N3 C20 C15 120.5(2) . . ? C20 C21 C22 108.4(2) . . ? C20 C21 H21 125.8 . . ? C22 C21 H21 125.8 . . ? C23 C22 C21 107.5(2) . . ? C23 C22 H22 126.3 . . ? C21 C22 H22 126.3 . . ? C22 C23 N3 107.0(2) . . ? C22 C23 C24 132.5(2) . . ? N3 C23 C24 120.3(2) . . ? C30 C24 C23 110.65(19) . . ? C30 C24 C25 113.4(2) . . ? C23 C24 C25 110.7(2) . . ? C30 C24 H24 107.3 . . ? C23 C24 H24 107.3 . . ? C25 C24 H24 107.3 . . ? N6 C25 C26 121.3(3) . . ? N6 C25 C24 115.5(2) . . ? C26 C25 C24 123.2(3) . . ? C25 C26 C27 119.7(3) . . ? C25 C26 H26 120.2 . . ? C27 C26 H26 120.2 . . ? C28 C27 C26 118.4(3) . . ? C28 C27 H27 120.8 . . ? C26 C27 H27 120.8 . . ? C29 C28 C27 118.8(3) . . ? C29 C28 H28 120.6 . . ? C27 C28 H28 120.6 . . ? N6 C29 C28 123.9(3) . . ? N6 C29 H29 118.0 . . ? C28 C29 H29 118.0 . . ? C31 C30 N4 106.4(2) . . ? C31 C30 C24 132.5(2) . . ? N4 C30 C24 121.0(2) . . ? C30 C31 C32 107.8(2) . . ? C30 C31 H31 126.1 . . ? C32 C31 H31 126.1 . . ? C33 C32 C31 108.3(2) . . ? C33 C32 H32 125.9 . . ? C31 C32 H32 125.9 . . ? C32 C33 N4 106.4(2) . . ? C32 C33 C34 133.4(3) . . ? N4 C33 C34 120.1(2) . . ? C1 C34 C33 109.45(19) . . ? C1 C34 C37 110.3(2) . . ? C33 C34 C37 109.3(2) . . ? C1 C34 C35 108.1(2) . . ? C33 C34 C35 108.4(2) . . ? C37 C34 C35 111.3(2) . . ? C36 C35 C34 115.3(2) . . ? C36 C35 H35A 108.5 . . ? C34 C35 H35A 108.5 . . ? C36 C35 H35B 108.5 . . ? C34 C35 H35B 108.5 . . ? H35A C35 H35B 107.5 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C38 C37 C34 115.8(2) . . ? C38 C37 H37A 108.3 . . ? C34 C37 H37A 108.3 . . ? C38 C37 H37B 108.3 . . ? C34 C37 H37B 108.3 . . ? H37A C37 H37B 107.4 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? N7 C39 C40 123.8(3) . . ? N7 C39 H39 118.1 . . ? C40 C39 H39 118.1 . . ? C41 C40 C39 118.0(3) . . ? C41 C40 H40 121.0 . . ? C39 C40 H40 121.0 . . ? C40 C41 C42 119.6(3) . . ? C40 C41 H41 120.2 . . ? C42 C41 H41 120.2 . . ? C41 C42 C43 119.5(3) . . ? C41 C42 H42 120.3 . . ? C43 C42 H42 120.3 . . ? N7 C43 C42 120.9(2) . . ? N7 C43 C44 115.0(2) . . ? C42 C43 C44 124.0(2) . . ? C57 C44 C43 115.7(2) 2_667 . ? C57 C44 C45 112.53(19) 2_667 . ? C43 C44 C45 111.36(19) . . ? C57 C44 H44 105.4 2_667 . ? C43 C44 H44 105.4 . . ? C45 C44 H44 105.4 . . ? C46 C45 N8 106.6(2) . . ? C46 C45 C44 133.5(2) . . ? N8 C45 C44 120.0(2) . . ? C45 C46 C47 107.8(3) . . ? C45 C46 H46 126.1 . . ? C47 C46 H46 126.1 . . ? C48 C47 C46 108.2(2) . . ? C48 C47 H47 125.9 . . ? C46 C47 H47 125.9 . . ? C47 C48 N8 106.5(2) . . ? C47 C48 C49 133.5(2) . . ? N8 C48 C49 120.0(2) . . ? C54 C49 C48 109.0(2) . . ? C54 C49 C50 109.2(2) . . ? C48 C49 C50 109.0(2) . . ? C54 C49 C52 109.7(2) . . ? C48 C49 C52 109.0(2) . . ? C50 C49 C52 110.8(2) . . ? C51 C50 C49 114.9(3) . . ? C51 C50 H50A 108.5 . . ? C49 C50 H50A 108.5 . . ? C51 C50 H50B 108.5 . . ? C49 C50 H50B 108.5 . . ? H50A C50 H50B 107.5 . . ? C50 C51 H51A 109.5 . . ? C50 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C50 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? C53 C52 C49 116.0(3) . . ? C53 C52 H52A 108.3 . . ? C49 C52 H52A 108.3 . . ? C53 C52 H52B 108.3 . . ? C49 C52 H52B 108.3 . . ? H52A C52 H52B 107.4 . . ? C52 C53 H53A 109.5 . . ? C52 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C52 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? C55 C54 N9 105.5(3) . . ? C55 C54 C49 133.4(3) . . ? N9 C54 C49 121.1(2) . . ? C54 C55 C56 108.9(2) . . ? C54 C55 H55 125.6 . . ? C56 C55 H55 125.6 . . ? C57 C56 C55 107.6(3) . . ? C57 C56 H56 126.2 . . ? C55 C56 H56 126.2 . . ? C56 C57 N9 106.6(2) . . ? C56 C57 C44 134.6(3) . 2_667 ? N9 C57 C44 118.6(2) . 2_667 ? C4 N1 C1 111.2(2) . . ? C4 N1 H1 124.1(16) . . ? C1 N1 H1 124.3(16) . . ? C11 N2 C14 111.1(2) . . ? C11 N2 H4 126.0(16) . . ? C14 N2 H4 122.9(16) . . ? C23 N3 C20 110.6(2) . . ? C23 N3 H6 120.2(15) . . ? C20 N3 H6 128.3(15) . . ? C33 N4 C30 111.1(2) . . ? C33 N4 H11 127.2(16) . . ? C30 N4 H11 121.6(15) . . ? C6 N5 C10 116.5(2) . . ? C25 N6 C29 117.9(3) . . ? C43 N7 C39 118.2(2) . . ? C45 N8 C48 110.9(2) . . ? C45 N8 H14 124.3(16) . . ? C48 N8 H14 123.5(17) . . ? C57 N9 C54 111.3(2) . . ? C57 N9 H15 122.3(17) . . ? C54 N9 H15 124.7(17) . . ? H1W O1 H2W 102(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 N1 C1 C2 C3 -1.2(3) . . . . ? C34 C1 C2 C3 178.2(3) . . . . ? C1 C2 C3 C4 0.8(3) . . . . ? C2 C3 C4 N1 -0.1(3) . . . . ? C2 C3 C4 C5 175.1(3) . . . . ? C3 C4 C5 C11 -101.6(3) . . . . ? N1 C4 C5 C11 72.9(3) . . . . ? C3 C4 C5 C6 131.0(3) . . . . ? N1 C4 C5 C6 -54.5(3) . . . . ? C4 C5 C6 N5 56.1(3) . . . . ? C11 C5 C6 N5 -72.4(3) . . . . ? C4 C5 C6 C7 -125.4(3) . . . . ? C11 C5 C6 C7 106.2(3) . . . . ? N5 C6 C7 C8 0.1(4) . . . . ? C5 C6 C7 C8 -178.4(3) . . . . ? C6 C7 C8 C9 -0.3(5) . . . . ? C7 C8 C9 C10 0.1(5) . . . . ? C8 C9 C10 N5 0.4(5) . . . . ? C4 C5 C11 C12 -157.1(3) . . . . ? C6 C5 C11 C12 -27.6(4) . . . . ? C4 C5 C11 N2 29.8(3) . . . . ? C6 C5 C11 N2 159.2(2) . . . . ? N2 C11 C12 C13 0.1(3) . . . . ? C5 C11 C12 C13 -173.8(2) . . . . ? C11 C12 C13 C14 -0.2(3) . . . . ? C12 C13 C14 N2 0.1(3) . . . . ? C12 C13 C14 C15 177.5(2) . . . . ? C13 C14 C15 C20 140.7(3) . . . . ? N2 C14 C15 C20 -42.3(3) . . . . ? C13 C14 C15 C16 -100.9(3) . . . . ? N2 C14 C15 C16 76.1(3) . . . . ? C13 C14 C15 C18 20.8(4) . . . . ? N2 C14 C15 C18 -162.2(2) . . . . ? C20 C15 C16 C17 -177.9(2) . . . . ? C14 C15 C16 C17 63.7(3) . . . . ? C18 C15 C16 C17 -56.1(3) . . . . ? C20 C15 C18 C19 60.3(3) . . . . ? C14 C15 C18 C19 179.2(2) . . . . ? C16 C15 C18 C19 -60.8(3) . . . . ? C14 C15 C20 C21 110.6(3) . . . . ? C16 C15 C20 C21 -8.0(4) . . . . ? C18 C15 C20 C21 -130.6(3) . . . . ? C14 C15 C20 N3 -66.9(3) . . . . ? C16 C15 C20 N3 174.5(2) . . . . ? C18 C15 C20 N3 51.9(3) . . . . ? N3 C20 C21 C22 0.6(3) . . . . ? C15 C20 C21 C22 -177.2(2) . . . . ? C20 C21 C22 C23 -0.5(3) . . . . ? C21 C22 C23 N3 0.3(3) . . . . ? C21 C22 C23 C24 173.6(2) . . . . ? C22 C23 C24 C30 -86.1(3) . . . . ? N3 C23 C24 C30 86.5(3) . . . . ? C22 C23 C24 C25 40.5(4) . . . . ? N3 C23 C24 C25 -146.9(2) . . . . ? C30 C24 C25 N6 -149.3(2) . . . . ? C23 C24 C25 N6 85.6(3) . . . . ? C30 C24 C25 C26 32.2(4) . . . . ? C23 C24 C25 C26 -92.9(3) . . . . ? N6 C25 C26 C27 -1.2(6) . . . . ? C24 C25 C26 C27 177.2(4) . . . . ? C25 C26 C27 C28 1.7(7) . . . . ? C26 C27 C28 C29 -0.5(7) . . . . ? C27 C28 C29 N6 -1.3(6) . . . . ? C23 C24 C30 C31 -154.4(3) . . . . ? C25 C24 C30 C31 80.5(3) . . . . ? C23 C24 C30 N4 29.3(3) . . . . ? C25 C24 C30 N4 -95.8(3) . . . . ? N4 C30 C31 C32 -0.4(3) . . . . ? C24 C30 C31 C32 -177.1(2) . . . . ? C30 C31 C32 C33 0.0(3) . . . . ? C31 C32 C33 N4 0.3(3) . . . . ? C31 C32 C33 C34 176.6(2) . . . . ? C2 C1 C34 C33 127.6(3) . . . . ? N1 C1 C34 C33 -53.0(3) . . . . ? C2 C1 C34 C37 -112.1(3) . . . . ? N1 C1 C34 C37 67.3(3) . . . . ? C2 C1 C34 C35 9.7(4) . . . . ? N1 C1 C34 C35 -170.9(2) . . . . ? C32 C33 C34 C1 132.5(3) . . . . ? N4 C33 C34 C1 -51.6(3) . . . . ? C32 C33 C34 C37 11.6(4) . . . . ? N4 C33 C34 C37 -172.5(2) . . . . ? C32 C33 C34 C35 -109.8(3) . . . . ? N4 C33 C34 C35 66.1(3) . . . . ? C1 C34 C35 C36 177.0(2) . . . . ? C33 C34 C35 C36 58.5(3) . . . . ? C37 C34 C35 C36 -61.8(3) . . . . ? C1 C34 C37 C38 56.9(3) . . . . ? C33 C34 C37 C38 177.3(2) . . . . ? C35 C34 C37 C38 -63.0(3) . . . . ? N7 C39 C40 C41 0.4(4) . . . . ? C39 C40 C41 C42 -1.9(4) . . . . ? C40 C41 C42 C43 1.5(4) . . . . ? C41 C42 C43 N7 0.4(4) . . . . ? C41 C42 C43 C44 -177.3(2) . . . . ? N7 C43 C44 C57 123.5(2) . . . 2_667 ? C42 C43 C44 C57 -58.6(3) . . . 2_667 ? N7 C43 C44 C45 -106.3(2) . . . . ? C42 C43 C44 C45 71.5(3) . . . . ? C57 C44 C45 C46 79.5(3) 2_667 . . . ? C43 C44 C45 C46 -52.3(4) . . . . ? C57 C44 C45 N8 -100.6(3) 2_667 . . . ? C43 C44 C45 N8 127.6(2) . . . . ? N8 C45 C46 C47 0.3(3) . . . . ? C44 C45 C46 C47 -179.8(2) . . . . ? C45 C46 C47 C48 -0.3(3) . . . . ? C46 C47 C48 N8 0.2(3) . . . . ? C46 C47 C48 C49 -177.5(3) . . . . ? C47 C48 C49 C54 -133.8(3) . . . . ? N8 C48 C49 C54 48.7(3) . . . . ? C47 C48 C49 C50 107.1(3) . . . . ? N8 C48 C49 C50 -70.4(3) . . . . ? C47 C48 C49 C52 -14.0(4) . . . . ? N8 C48 C49 C52 168.4(2) . . . . ? C54 C49 C50 C51 -180.0(2) . . . . ? C48 C49 C50 C51 -61.0(3) . . . . ? C52 C49 C50 C51 59.1(3) . . . . ? C54 C49 C52 C53 -62.4(3) . . . . ? C48 C49 C52 C53 178.3(2) . . . . ? C50 C49 C52 C53 58.3(3) . . . . ? C48 C49 C54 C55 -137.4(3) . . . . ? C50 C49 C54 C55 -18.4(4) . . . . ? C52 C49 C54 C55 103.2(3) . . . . ? C48 C49 C54 N9 42.8(3) . . . . ? C50 C49 C54 N9 161.8(2) . . . . ? C52 C49 C54 N9 -76.6(3) . . . . ? N9 C54 C55 C56 -1.2(3) . . . . ? C49 C54 C55 C56 178.9(3) . . . . ? C54 C55 C56 C57 0.4(3) . . . . ? C55 C56 C57 N9 0.7(3) . . . . ? C55 C56 C57 C44 -174.2(3) . . . 2_667 ? C3 C4 N1 C1 -0.7(3) . . . . ? C5 C4 N1 C1 -176.3(2) . . . . ? C2 C1 N1 C4 1.2(3) . . . . ? C34 C1 N1 C4 -178.3(2) . . . . ? C12 C11 N2 C14 0.0(3) . . . . ? C5 C11 N2 C14 174.6(2) . . . . ? C13 C14 N2 C11 -0.1(3) . . . . ? C15 C14 N2 C11 -177.8(2) . . . . ? C22 C23 N3 C20 0.1(3) . . . . ? C24 C23 N3 C20 -174.2(2) . . . . ? C21 C20 N3 C23 -0.4(3) . . . . ? C15 C20 N3 C23 177.7(2) . . . . ? C32 C33 N4 C30 -0.6(3) . . . . ? C34 C33 N4 C30 -177.5(2) . . . . ? C31 C30 N4 C33 0.6(3) . . . . ? C24 C30 N4 C33 177.77(19) . . . . ? C7 C6 N5 C10 0.3(4) . . . . ? C5 C6 N5 C10 178.9(2) . . . . ? C9 C10 N5 C6 -0.6(4) . . . . ? C26 C25 N6 C29 -0.5(4) . . . . ? C24 C25 N6 C29 -179.0(3) . . . . ? C28 C29 N6 C25 1.8(5) . . . . ? C42 C43 N7 C39 -1.9(3) . . . . ? C44 C43 N7 C39 176.0(2) . . . . ? C40 C39 N7 C43 1.5(4) . . . . ? C46 C45 N8 C48 -0.2(3) . . . . ? C44 C45 N8 C48 179.9(2) . . . . ? C47 C48 N8 C45 0.0(3) . . . . ? C49 C48 N8 C45 178.1(2) . . . . ? C56 C57 N9 C54 -1.5(3) . . . . ? C44 C57 N9 C54 174.3(2) 2_667 . . . ? C55 C54 N9 C57 1.7(3) . . . . ? C49 C54 N9 C57 -178.4(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1W N6 0.93(3) 1.93(3) 2.856(3) 169(3) . N3 H6 N7 0.93(2) 2.03(2) 2.949(3) 172(2) 1_655 N8 H14 O1 0.89(2) 2.21(3) 3.035(3) 154(2) 1_455 N9 H15 O1 0.86(2) 2.21(2) 3.030(3) 159(2) 2_767 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.175 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.034 data_calix[4]phyrin _database_code_depnum_ccdc_archive 'CCDC 896706' #TrackingRef 'gmtg.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H38 N6' _chemical_formula_weight 578.74 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 13.937(5) _cell_length_b 19.444(7) _cell_length_c 11.779(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.961(14) _cell_angle_gamma 90.00 _cell_volume 3134(2) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 18310 _cell_measurement_theta_min 1.82 _cell_measurement_theta_max 25.00 _exptl_crystal_description Plate _exptl_crystal_colour red _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.227 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9825 _exptl_absorpt_correction_T_max 0.9963 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-APEX-II CCD area detector' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18310 _diffrn_reflns_av_R_equivalents 0.0588 _diffrn_reflns_av_sigmaI/netI 0.0563 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4983 _reflns_number_gt 3592 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0652P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(3) _refine_ls_number_reflns 4983 _refine_ls_number_parameters 403 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0810 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1266 _refine_ls_wR_factor_gt 0.1126 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.042 _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 C1 C 0.3998(2) 0.50770(17) 0.5721(3) 0.0432(8) Uani 1 1 d . . . C2 C 0.3392(2) 0.56742(18) 0.5545(3) 0.0554(10) Uani 1 1 d . . . H2 H 0.3472 0.6075 0.5982 0.066 Uiso 1 1 calc R . . C3 C 0.2676(2) 0.55434(19) 0.4613(3) 0.0535(10) Uani 1 1 d . . . H3 H 0.2176 0.5842 0.4293 0.064 Uiso 1 1 calc R . . C4 C 0.2825(2) 0.48751(16) 0.4220(3) 0.0411(8) Uani 1 1 d . . . C5 C 0.2249(2) 0.45065(16) 0.3312(3) 0.0403(8) Uani 1 1 d . . . C6 C 0.1479(2) 0.48949(16) 0.2500(3) 0.0434(8) Uani 1 1 d . . . C7 C 0.1732(3) 0.5395(2) 0.1797(4) 0.0654(11) Uani 1 1 d . . . H7 H 0.2385 0.5515 0.1848 0.078 Uiso 1 1 calc R . . C8 C 0.1014(3) 0.5724(2) 0.1010(4) 0.0724(13) Uani 1 1 d . . . H8 H 0.1177 0.6050 0.0501 0.087 Uiso 1 1 calc R . . C9 C 0.0069(3) 0.5558(2) 0.1002(4) 0.0724(13) Uani 1 1 d . . . H9 H -0.0437 0.5773 0.0498 0.087 Uiso 1 1 calc R . . C10 C -0.0119(3) 0.5070(2) 0.1749(4) 0.0813(15) Uani 1 1 d . . . H10 H -0.0771 0.4964 0.1743 0.098 Uiso 1 1 calc R . . C11 C 0.2344(2) 0.37952(17) 0.3107(3) 0.0410(8) Uani 1 1 d . . . C12 C 0.1822(2) 0.3378(2) 0.2239(3) 0.0506(9) Uani 1 1 d . . . H12 H 0.1325 0.3518 0.1641 0.061 Uiso 1 1 calc R . . C13 C 0.2182(3) 0.27200(19) 0.2438(3) 0.0519(10) Uani 1 1 d . . . H13 H 0.1966 0.2332 0.2003 0.062 Uiso 1 1 calc R . . C14 C 0.2928(2) 0.27422(17) 0.3407(3) 0.0453(9) Uani 1 1 d . . . C15 C 0.3554(2) 0.21693(17) 0.4064(3) 0.0477(9) Uani 1 1 d . . . C16 C 0.3207(3) 0.14699(19) 0.3510(4) 0.0693(12) Uani 1 1 d . . . H16A H 0.2501 0.1449 0.3419 0.083 Uiso 1 1 calc R . . H16B H 0.3364 0.1454 0.2743 0.083 Uiso 1 1 calc R . . C17 C 0.3635(4) 0.0829(2) 0.4170(5) 0.0968(17) Uani 1 1 d . . . H17A H 0.3371 0.0425 0.3757 0.145 Uiso 1 1 calc R . . H17B H 0.3471 0.0829 0.4926 0.145 Uiso 1 1 calc R . . H17C H 0.4333 0.0831 0.4243 0.145 Uiso 1 1 calc R . . C18 C 0.3466(3) 0.2205(2) 0.5344(3) 0.0586(10) Uani 1 1 d . . . H18A H 0.3876 0.1849 0.5763 0.070 Uiso 1 1 calc R . . H18B H 0.3717 0.2645 0.5654 0.070 Uiso 1 1 calc R . . C19 C 0.2429(3) 0.2118(3) 0.5573(5) 0.0922(16) Uani 1 1 d . . . H19A H 0.2443 0.2141 0.6390 0.138 Uiso 1 1 calc R . . H19B H 0.2175 0.1680 0.5283 0.138 Uiso 1 1 calc R . . H19C H 0.2020 0.2478 0.5190 0.138 Uiso 1 1 calc R . . C20 C 0.4613(2) 0.22998(17) 0.3975(3) 0.0458(9) Uani 1 1 d . . . C21 C 0.5233(3) 0.19233(18) 0.3382(4) 0.0583(10) Uani 1 1 d . . . H21 H 0.5069 0.1525 0.2952 0.070 Uiso 1 1 calc R . . C22 C 0.6116(3) 0.22493(18) 0.3555(3) 0.0546(10) Uani 1 1 d . . . H22 H 0.6663 0.2117 0.3265 0.066 Uiso 1 1 calc R . . C23 C 0.6037(2) 0.28265(16) 0.4259(3) 0.0407(8) Uani 1 1 d . . . C24 C 0.6727(2) 0.33465(17) 0.4635(3) 0.0385(8) Uani 1 1 d . . . C25 C 0.7726(2) 0.32550(17) 0.4348(3) 0.0421(8) Uani 1 1 d . . . C26 C 0.8329(3) 0.2744(2) 0.4821(4) 0.0815(15) Uani 1 1 d . . . H26 H 0.8135 0.2436 0.5338 0.098 Uiso 1 1 calc R . . C27 C 0.9242(3) 0.2685(3) 0.4525(5) 0.1008(18) Uani 1 1 d . . . H27 H 0.9678 0.2349 0.4866 0.121 Uiso 1 1 calc R . . C28 C 0.9491(3) 0.3120(3) 0.3738(4) 0.0762(13) Uani 1 1 d . . . H28 H 1.0081 0.3076 0.3486 0.091 Uiso 1 1 calc R . . C29 C 0.8853(3) 0.3619(2) 0.3334(4) 0.0671(11) Uani 1 1 d . . . H29 H 0.9041 0.3931 0.2818 0.081 Uiso 1 1 calc R . . C30 C 0.6552(2) 0.39375(17) 0.5248(3) 0.0371(8) Uani 1 1 d . . . C31 C 0.7210(2) 0.44456(19) 0.5745(3) 0.0504(9) Uani 1 1 d . . . H31 H 0.7866 0.4474 0.5691 0.060 Uiso 1 1 calc R . . C32 C 0.6712(2) 0.48977(18) 0.6329(3) 0.0523(10) Uani 1 1 d . . . H32 H 0.6971 0.5281 0.6752 0.063 Uiso 1 1 calc R . . C33 C 0.5737(2) 0.46688(17) 0.6164(3) 0.0398(8) Uani 1 1 d . . . C34 C 0.4888(2) 0.49483(17) 0.6664(3) 0.0415(8) Uani 1 1 d . . . C35 C 0.4601(2) 0.4394(2) 0.7494(3) 0.0564(10) Uani 1 1 d . . . H35A H 0.4114 0.4591 0.7887 0.068 Uiso 1 1 calc R . . H35B H 0.4297 0.4012 0.7031 0.068 Uiso 1 1 calc R . . C36 C 0.5414(4) 0.4120(3) 0.8382(4) 0.0995(16) Uani 1 1 d . . . H36A H 0.5161 0.3785 0.8849 0.149 Uiso 1 1 calc R . . H36B H 0.5712 0.4489 0.8864 0.149 Uiso 1 1 calc R . . H36C H 0.5892 0.3907 0.8008 0.149 Uiso 1 1 calc R . . C37 C 0.5182(3) 0.56103(19) 0.7360(3) 0.0551(10) Uani 1 1 d . . . H37A H 0.4645 0.5743 0.7730 0.066 Uiso 1 1 calc R . . H37B H 0.5736 0.5505 0.7969 0.066 Uiso 1 1 calc R . . C38 C 0.5452(3) 0.6230(2) 0.6685(4) 0.0699(12) Uani 1 1 d . . . H38A H 0.5619 0.6612 0.7201 0.105 Uiso 1 1 calc R . . H38B H 0.4905 0.6352 0.6092 0.105 Uiso 1 1 calc R . . H38C H 0.6001 0.6115 0.6336 0.105 Uiso 1 1 calc R . . N1 N 0.36445(17) 0.45963(13) 0.4940(2) 0.0392(6) Uani 1 1 d . . . N2 N 0.05558(19) 0.47301(17) 0.2492(3) 0.0675(10) Uani 1 1 d . . . N3 N 0.30251(19) 0.33864(15) 0.3793(3) 0.0451(7) Uani 1 1 d D . . H1 H 0.337(2) 0.3512(19) 0.430(3) 0.054 Uiso 1 1 d D . . N4 N 0.50910(18) 0.28387(13) 0.4502(2) 0.0424(7) Uani 1 1 d . . . N5 N 0.7981(2) 0.37104(16) 0.3600(3) 0.0536(8) Uani 1 1 d . . . N6 N 0.56626(18) 0.40982(14) 0.5528(2) 0.0391(7) Uani 1 1 d D . . H4 H 0.523(2) 0.3898(17) 0.533(3) 0.047 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0362(17) 0.049(2) 0.045(2) -0.0036(17) 0.0079(15) 0.0037(16) C2 0.052(2) 0.049(2) 0.063(3) -0.0092(19) 0.0059(19) 0.0096(17) C3 0.0385(18) 0.052(2) 0.065(3) -0.005(2) -0.0015(18) 0.0103(16) C4 0.0302(15) 0.0421(19) 0.050(2) 0.0038(17) 0.0046(15) 0.0037(14) C5 0.0327(16) 0.0472(19) 0.041(2) 0.0044(17) 0.0074(14) 0.0024(15) C6 0.0357(18) 0.0477(19) 0.045(2) 0.0035(17) 0.0033(15) 0.0029(15) C7 0.045(2) 0.081(3) 0.072(3) 0.022(2) 0.018(2) 0.005(2) C8 0.059(3) 0.086(3) 0.075(3) 0.036(3) 0.018(2) 0.017(2) C9 0.050(2) 0.085(3) 0.073(3) 0.022(3) -0.012(2) 0.010(2) C10 0.039(2) 0.088(3) 0.107(4) 0.036(3) -0.010(2) 0.002(2) C11 0.0307(16) 0.052(2) 0.039(2) 0.0042(17) 0.0019(14) -0.0021(15) C12 0.0457(19) 0.062(2) 0.040(2) -0.0014(18) -0.0015(16) -0.0051(17) C13 0.050(2) 0.053(2) 0.050(2) -0.0093(19) 0.0026(18) -0.0120(17) C14 0.0421(19) 0.043(2) 0.052(2) 0.0030(17) 0.0104(17) -0.0091(16) C15 0.046(2) 0.045(2) 0.052(2) 0.0031(17) 0.0090(18) -0.0115(16) C16 0.065(2) 0.046(2) 0.095(3) -0.003(2) 0.010(2) -0.0191(19) C17 0.107(4) 0.046(3) 0.138(5) 0.017(3) 0.024(3) -0.009(2) C18 0.057(2) 0.064(2) 0.056(3) 0.017(2) 0.0136(19) -0.0114(18) C19 0.074(3) 0.121(4) 0.087(4) 0.020(3) 0.030(3) -0.014(3) C20 0.050(2) 0.0371(19) 0.049(2) 0.0015(17) 0.0078(17) -0.0012(16) C21 0.071(2) 0.0411(19) 0.065(3) -0.012(2) 0.019(2) -0.001(2) C22 0.057(2) 0.042(2) 0.071(3) 0.0015(19) 0.028(2) 0.0079(18) C23 0.0362(17) 0.0412(19) 0.046(2) 0.0050(16) 0.0115(16) 0.0058(15) C24 0.0335(17) 0.046(2) 0.0368(19) 0.0090(16) 0.0075(14) 0.0054(14) C25 0.0400(17) 0.046(2) 0.043(2) 0.0043(17) 0.0143(15) 0.0058(16) C26 0.064(3) 0.086(3) 0.106(4) 0.041(3) 0.046(3) 0.030(2) C27 0.068(3) 0.111(4) 0.134(5) 0.035(4) 0.047(3) 0.048(3) C28 0.052(2) 0.099(4) 0.087(3) -0.018(3) 0.038(2) -0.001(3) C29 0.054(2) 0.092(3) 0.063(3) 0.001(2) 0.029(2) -0.015(2) C30 0.0279(16) 0.0440(19) 0.040(2) 0.0026(16) 0.0072(14) 0.0016(14) C31 0.0302(16) 0.058(2) 0.063(2) -0.010(2) 0.0081(16) -0.0067(16) C32 0.0387(18) 0.057(2) 0.060(3) -0.016(2) 0.0069(17) -0.0072(17) C33 0.0356(17) 0.045(2) 0.038(2) -0.0081(17) 0.0043(14) -0.0024(15) C34 0.0369(17) 0.052(2) 0.036(2) -0.0055(16) 0.0072(15) 0.0008(15) C35 0.046(2) 0.076(3) 0.051(2) 0.008(2) 0.0189(18) 0.0048(18) C36 0.091(4) 0.138(4) 0.068(3) 0.029(3) 0.010(3) 0.011(3) C37 0.058(2) 0.059(2) 0.047(2) -0.0183(19) 0.0064(17) 0.0028(17) C38 0.068(3) 0.068(3) 0.072(3) -0.013(2) 0.008(2) -0.013(2) N1 0.0364(13) 0.0448(16) 0.0343(16) -0.0041(13) 0.0017(12) 0.0018(12) N2 0.0324(16) 0.083(2) 0.083(2) 0.029(2) -0.0013(16) -0.0025(15) N3 0.0393(16) 0.0451(18) 0.047(2) -0.0029(15) -0.0029(13) -0.0033(14) N4 0.0401(15) 0.0388(16) 0.0485(18) 0.0027(13) 0.0089(13) 0.0000(12) N5 0.0469(17) 0.067(2) 0.049(2) 0.0033(17) 0.0167(15) -0.0051(15) N6 0.0288(15) 0.0452(18) 0.0429(17) -0.0062(14) 0.0063(13) -0.0050(12) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.338(4) . ? C1 C2 1.427(5) . ? C1 C34 1.521(4) . ? C2 C3 1.359(5) . ? C2 H2 0.9300 . ? C3 C4 1.409(5) . ? C3 H3 0.9300 . ? C4 N1 1.396(4) . ? C4 C5 1.406(4) . ? C5 C11 1.414(4) . ? C5 C6 1.498(4) . ? C6 N2 1.324(4) . ? C6 C7 1.367(5) . ? C7 C8 1.384(5) . ? C7 H7 0.9300 . ? C8 C9 1.355(5) . ? C8 H8 0.9300 . ? C9 C10 1.352(6) . ? C9 H9 0.9300 . ? C10 N2 1.333(5) . ? C10 H10 0.9300 . ? C11 N3 1.376(4) . ? C11 C12 1.396(5) . ? C12 C13 1.379(5) . ? C12 H12 0.9300 . ? C13 C14 1.391(5) . ? C13 H13 0.9300 . ? C14 N3 1.331(4) . ? C14 C15 1.531(5) . ? C15 C20 1.520(5) . ? C15 C18 1.537(5) . ? C15 C16 1.546(5) . ? C16 C17 1.529(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.528(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 N4 1.330(4) . ? C20 C21 1.414(5) . ? C21 C22 1.364(5) . ? C21 H21 0.9300 . ? C22 C23 1.412(5) . ? C22 H22 0.9300 . ? C23 N4 1.402(4) . ? C23 C24 1.407(4) . ? C24 C30 1.403(4) . ? C24 C25 1.505(4) . ? C25 N5 1.344(4) . ? C25 C26 1.351(5) . ? C26 C27 1.386(6) . ? C26 H26 0.9300 . ? C27 C28 1.348(7) . ? C27 H27 0.9300 . ? C28 C29 1.341(6) . ? C28 H28 0.9300 . ? C29 N5 1.323(5) . ? C29 H29 0.9300 . ? C30 N6 1.378(4) . ? C30 C31 1.398(4) . ? C31 C32 1.382(5) . ? C31 H31 0.9300 . ? C32 C33 1.407(4) . ? C32 H32 0.9300 . ? C33 N6 1.332(4) . ? C33 C34 1.519(5) . ? C34 C37 1.539(5) . ? C34 C35 1.557(5) . ? C35 C36 1.487(6) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 C38 1.530(6) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? N3 H1 0.73(3) . ? N6 H4 0.72(3) . ? 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 N1 C1 C2 109.8(3) . . ? N1 C1 C34 122.0(3) . . ? C2 C1 C34 128.2(3) . . ? C3 C2 C1 106.8(3) . . ? C3 C2 H2 126.6 . . ? C1 C2 H2 126.6 . . ? C2 C3 C4 107.8(3) . . ? C2 C3 H3 126.1 . . ? C4 C3 H3 126.1 . . ? N1 C4 C5 123.2(3) . . ? N1 C4 C3 108.2(3) . . ? C5 C4 C3 128.5(3) . . ? C4 C5 C11 124.7(3) . . ? C4 C5 C6 117.7(3) . . ? C11 C5 C6 117.6(3) . . ? N2 C6 C7 122.0(3) . . ? N2 C6 C5 117.3(3) . . ? C7 C6 C5 120.6(3) . . ? C6 C7 C8 119.8(4) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C9 C8 C7 118.2(4) . . ? C9 C8 H8 120.9 . . ? C7 C8 H8 120.9 . . ? C10 C9 C8 118.1(3) . . ? C10 C9 H9 121.0 . . ? C8 C9 H9 121.0 . . ? N2 C10 C9 125.1(4) . . ? N2 C10 H10 117.4 . . ? C9 C10 H10 117.4 . . ? N3 C11 C12 107.4(3) . . ? N3 C11 C5 122.8(3) . . ? C12 C11 C5 129.8(3) . . ? C13 C12 C11 107.0(3) . . ? C13 C12 H12 126.5 . . ? C11 C12 H12 126.5 . . ? C12 C13 C14 107.6(3) . . ? C12 C13 H13 126.2 . . ? C14 C13 H13 126.2 . . ? N3 C14 C13 108.7(3) . . ? N3 C14 C15 120.0(3) . . ? C13 C14 C15 131.1(3) . . ? C20 C15 C14 108.1(3) . . ? C20 C15 C18 108.7(3) . . ? C14 C15 C18 108.6(3) . . ? C20 C15 C16 110.4(3) . . ? C14 C15 C16 108.9(3) . . ? C18 C15 C16 112.1(3) . . ? C17 C16 C15 116.2(3) . . ? C17 C16 H16A 108.2 . . ? C15 C16 H16A 108.2 . . ? C17 C16 H16B 108.2 . . ? C15 C16 H16B 108.2 . . ? H16A C16 H16B 107.4 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C15 115.0(3) . . ? C19 C18 H18A 108.5 . . ? C15 C18 H18A 108.5 . . ? C19 C18 H18B 108.5 . . ? C15 C18 H18B 108.5 . . ? H18A C18 H18B 107.5 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N4 C20 C21 109.8(3) . . ? N4 C20 C15 120.4(3) . . ? C21 C20 C15 129.8(3) . . ? C22 C21 C20 107.7(3) . . ? C22 C21 H21 126.1 . . ? C20 C21 H21 126.1 . . ? C21 C22 C23 106.8(3) . . ? C21 C22 H22 126.6 . . ? C23 C22 H22 126.6 . . ? N4 C23 C24 122.4(3) . . ? N4 C23 C22 108.3(3) . . ? C24 C23 C22 129.2(3) . . ? C30 C24 C23 125.2(3) . . ? C30 C24 C25 118.1(3) . . ? C23 C24 C25 116.8(3) . . ? N5 C25 C26 122.2(3) . . ? N5 C25 C24 116.2(3) . . ? C26 C25 C24 121.6(3) . . ? C25 C26 C27 119.1(4) . . ? C25 C26 H26 120.5 . . ? C27 C26 H26 120.5 . . ? C28 C27 C26 119.3(4) . . ? C28 C27 H27 120.3 . . ? C26 C27 H27 120.3 . . ? C29 C28 C27 117.3(4) . . ? C29 C28 H28 121.4 . . ? C27 C28 H28 121.4 . . ? N5 C29 C28 126.1(4) . . ? N5 C29 H29 116.9 . . ? C28 C29 H29 116.9 . . ? N6 C30 C31 106.7(3) . . ? N6 C30 C24 124.1(3) . . ? C31 C30 C24 129.1(3) . . ? C32 C31 C30 107.9(3) . . ? C32 C31 H31 126.1 . . ? C30 C31 H31 126.1 . . ? C31 C32 C33 107.0(3) . . ? C31 C32 H32 126.5 . . ? C33 C32 H32 126.5 . . ? N6 C33 C32 108.1(3) . . ? N6 C33 C34 122.2(3) . . ? C32 C33 C34 129.5(3) . . ? C33 C34 C1 111.3(3) . . ? C33 C34 C37 110.9(3) . . ? C1 C34 C37 110.4(3) . . ? C33 C34 C35 107.9(3) . . ? C1 C34 C35 107.6(3) . . ? C37 C34 C35 108.6(3) . . ? C36 C35 C34 116.0(3) . . ? C36 C35 H35A 108.3 . . ? C34 C35 H35A 108.3 . . ? C36 C35 H35B 108.3 . . ? C34 C35 H35B 108.3 . . ? H35A C35 H35B 107.4 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C38 C37 C34 116.7(3) . . ? C38 C37 H37A 108.1 . . ? C34 C37 H37A 108.1 . . ? C38 C37 H37B 108.1 . . ? C34 C37 H37B 108.1 . . ? H37A C37 H37B 107.3 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C1 N1 C4 107.4(3) . . ? C6 N2 C10 116.6(3) . . ? C14 N3 C11 109.2(3) . . ? C14 N3 H1 127(3) . . ? C11 N3 H1 124(3) . . ? C20 N4 C23 107.4(3) . . ? C29 N5 C25 115.9(3) . . ? C33 N6 C30 110.2(3) . . ? C33 N6 H4 127(3) . . ? C30 N6 H4 123(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 N1 C1 C2 C3 -1.5(4) . . . . ? C34 C1 C2 C3 -178.4(3) . . . . ? C1 C2 C3 C4 0.5(4) . . . . ? C2 C3 C4 N1 0.7(4) . . . . ? C2 C3 C4 C5 177.2(3) . . . . ? N1 C4 C5 C11 8.4(5) . . . . ? C3 C4 C5 C11 -167.6(4) . . . . ? N1 C4 C5 C6 -171.4(3) . . . . ? C3 C4 C5 C6 12.6(5) . . . . ? C4 C5 C6 N2 -114.7(4) . . . . ? C11 C5 C6 N2 65.4(4) . . . . ? C4 C5 C6 C7 65.6(5) . . . . ? C11 C5 C6 C7 -114.3(4) . . . . ? N2 C6 C7 C8 -3.0(6) . . . . ? C5 C6 C7 C8 176.6(4) . . . . ? C6 C7 C8 C9 3.1(7) . . . . ? C7 C8 C9 C10 -1.3(7) . . . . ? C8 C9 C10 N2 -0.7(8) . . . . ? C4 C5 C11 N3 0.1(5) . . . . ? C6 C5 C11 N3 180.0(3) . . . . ? C4 C5 C11 C12 -179.7(4) . . . . ? C6 C5 C11 C12 0.2(5) . . . . ? N3 C11 C12 C13 1.5(4) . . . . ? C5 C11 C12 C13 -178.7(4) . . . . ? C11 C12 C13 C14 -1.0(4) . . . . ? C12 C13 C14 N3 0.1(4) . . . . ? C12 C13 C14 C15 176.5(3) . . . . ? N3 C14 C15 C20 -66.7(4) . . . . ? C13 C14 C15 C20 117.3(4) . . . . ? N3 C14 C15 C18 51.1(4) . . . . ? C13 C14 C15 C18 -125.0(4) . . . . ? N3 C14 C15 C16 173.4(3) . . . . ? C13 C14 C15 C16 -2.7(5) . . . . ? C20 C15 C16 C17 71.1(4) . . . . ? C14 C15 C16 C17 -170.4(4) . . . . ? C18 C15 C16 C17 -50.2(5) . . . . ? C20 C15 C18 C19 177.2(3) . . . . ? C14 C15 C18 C19 59.8(4) . . . . ? C16 C15 C18 C19 -60.6(4) . . . . ? C14 C15 C20 N4 68.0(4) . . . . ? C18 C15 C20 N4 -49.7(4) . . . . ? C16 C15 C20 N4 -173.0(3) . . . . ? C14 C15 C20 C21 -111.8(4) . . . . ? C18 C15 C20 C21 130.5(4) . . . . ? C16 C15 C20 C21 7.2(5) . . . . ? N4 C20 C21 C22 -0.3(4) . . . . ? C15 C20 C21 C22 179.5(3) . . . . ? C20 C21 C22 C23 0.2(4) . . . . ? C21 C22 C23 N4 0.0(4) . . . . ? C21 C22 C23 C24 -176.5(3) . . . . ? N4 C23 C24 C30 -2.3(5) . . . . ? C22 C23 C24 C30 173.8(4) . . . . ? N4 C23 C24 C25 177.9(3) . . . . ? C22 C23 C24 C25 -6.1(5) . . . . ? C30 C24 C25 N5 -66.5(4) . . . . ? C23 C24 C25 N5 113.4(3) . . . . ? C30 C24 C25 C26 113.4(4) . . . . ? C23 C24 C25 C26 -66.7(4) . . . . ? N5 C25 C26 C27 -0.1(7) . . . . ? C24 C25 C26 C27 -180.0(4) . . . . ? C25 C26 C27 C28 -2.7(8) . . . . ? C26 C27 C28 C29 4.1(8) . . . . ? C27 C28 C29 N5 -2.9(7) . . . . ? C23 C24 C30 N6 -2.4(5) . . . . ? C25 C24 C30 N6 177.4(3) . . . . ? C23 C24 C30 C31 173.6(3) . . . . ? C25 C24 C30 C31 -6.6(5) . . . . ? N6 C30 C31 C32 0.9(4) . . . . ? C24 C30 C31 C32 -175.6(3) . . . . ? C30 C31 C32 C33 -1.2(4) . . . . ? C31 C32 C33 N6 1.1(4) . . . . ? C31 C32 C33 C34 176.3(3) . . . . ? N6 C33 C34 C1 -56.7(4) . . . . ? C32 C33 C34 C1 128.7(4) . . . . ? N6 C33 C34 C37 179.9(3) . . . . ? C32 C33 C34 C37 5.4(5) . . . . ? N6 C33 C34 C35 61.1(4) . . . . ? C32 C33 C34 C35 -113.5(4) . . . . ? N1 C1 C34 C33 51.1(4) . . . . ? C2 C1 C34 C33 -132.3(4) . . . . ? N1 C1 C34 C37 174.7(3) . . . . ? C2 C1 C34 C37 -8.7(5) . . . . ? N1 C1 C34 C35 -66.9(4) . . . . ? C2 C1 C34 C35 109.7(4) . . . . ? C33 C34 C35 C36 51.2(4) . . . . ? C1 C34 C35 C36 171.4(4) . . . . ? C37 C34 C35 C36 -69.1(4) . . . . ? C33 C34 C37 C38 63.9(4) . . . . ? C1 C34 C37 C38 -59.9(4) . . . . ? C35 C34 C37 C38 -177.6(3) . . . . ? C2 C1 N1 C4 1.9(4) . . . . ? C34 C1 N1 C4 179.0(3) . . . . ? C5 C4 N1 C1 -178.3(3) . . . . ? C3 C4 N1 C1 -1.6(4) . . . . ? C7 C6 N2 C10 1.0(6) . . . . ? C5 C6 N2 C10 -178.6(4) . . . . ? C9 C10 N2 C6 0.9(7) . . . . ? C13 C14 N3 C11 0.9(4) . . . . ? C15 C14 N3 C11 -176.0(3) . . . . ? C12 C11 N3 C14 -1.5(4) . . . . ? C5 C11 N3 C14 178.7(3) . . . . ? C21 C20 N4 C23 0.3(4) . . . . ? C15 C20 N4 C23 -179.5(3) . . . . ? C24 C23 N4 C20 176.6(3) . . . . ? C22 C23 N4 C20 -0.1(4) . . . . ? C28 C29 N5 C25 0.1(6) . . . . ? C26 C25 N5 C29 1.4(5) . . . . ? C24 C25 N5 C29 -178.7(3) . . . . ? C32 C33 N6 C30 -0.6(4) . . . . ? C34 C33 N6 C30 -176.2(3) . . . . ? C31 C30 N6 C33 -0.2(4) . . . . ? C24 C30 N6 C33 176.6(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H1 N1 0.73(3) 2.25(3) 2.768(4) 129(4) . N6 H4 N4 0.72(3) 2.27(3) 2.780(4) 129(3) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.284 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.037