# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_address ;Institute of Chemistry Chinese Academy of Sciences Beijing 100190 P. R. China ; _publ_contact_author_address ;Institute of Chemistry Chinese Academy of Sciences Beijing 100190 P. R. China ; _publ_contact_author_email huanggx@iccas.ac.cn _publ_contact_author_fax 86-10-62559373 _publ_contact_author_phone 86-10-62639355 _publ_contact_author_name 'Guangxi Huang' _publ_author_name 'Guangxi Huang' data_mx1300 _database_code_depnum_ccdc_archive 'CCDC 873727' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C46 H32 N4, 2(C H4 O)' _chemical_formula_sum 'C48 H40 N4 O2' _chemical_formula_weight 704.84 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 monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.118(3) _cell_length_b 9.4837(19) _cell_length_c 34.086(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.080(4) _cell_angle_gamma 90.00 _cell_volume 4239.6(15) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10374 _cell_measurement_theta_min 1.20 _cell_measurement_theta_max 26.37 _exptl_crystal_description palte _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.104 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9865 _exptl_absorpt_correction_T_max 0.9919 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_device_type 'MM007-HF CCD(Saturn 724+)' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24304 _diffrn_reflns_av_R_equivalents 0.0547 _diffrn_reflns_av_sigmaI/netI 0.0564 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7450 _reflns_number_gt 6331 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Olex2 Ver 1.1' _computing_publication_material 'SHELX97 (Sheldrick, 2008)' _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^)+(0.0583P)^2^+3.3907P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7450 _refine_ls_number_parameters 491 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0919 _refine_ls_R_factor_gt 0.0777 _refine_ls_wR_factor_ref 0.1811 _refine_ls_wR_factor_gt 0.1719 _refine_ls_goodness_of_fit_ref 1.141 _refine_ls_restrained_S_all 1.141 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2421(3) -0.0588(4) 0.63191(9) 0.0977(10) Uani 1 1 d . . . H1 H 0.2486 -0.1165 0.6134 0.147 Uiso 1 1 calc R . . O2 O 0.3093(3) 0.2318(5) 0.51115(9) 0.1228(15) Uani 1 1 d . . . H2 H 0.3226 0.2007 0.4887 0.184 Uiso 1 1 calc R . . N1 N 1.20411(16) 0.1579(3) 0.72793(7) 0.0402(6) Uani 1 1 d . . . N2 N 0.3686(2) 0.3404(3) 0.93667(7) 0.0484(7) Uani 1 1 d . . . N3 N -0.09872(19) 0.7048(3) 0.63870(9) 0.0556(7) Uani 1 1 d . . . N4 N 0.7503(2) 0.2338(4) 0.43549(8) 0.0664(9) Uani 1 1 d . . . C1 C 0.51828(18) 0.4005(3) 0.66494(8) 0.0318(6) Uani 1 1 d . . . C2 C 0.56953(18) 0.3751(3) 0.69899(8) 0.0312(6) Uani 1 1 d . . . C3 C 0.67912(18) 0.3322(3) 0.69960(8) 0.0308(6) Uani 1 1 d . . . C4 C 0.75521(19) 0.4136(3) 0.68266(8) 0.0337(6) Uani 1 1 d . . . H4 H 0.7370 0.4968 0.6686 0.040 Uiso 1 1 calc R . . C5 C 0.85675(19) 0.3750(3) 0.68596(8) 0.0345(6) Uani 1 1 d . . . H5 H 0.9071 0.4328 0.6744 0.041 Uiso 1 1 calc R . . C6 C 0.88673(18) 0.2535(3) 0.70586(8) 0.0314(6) Uani 1 1 d . . . C7 C 0.81062(19) 0.1694(3) 0.72168(8) 0.0355(6) Uani 1 1 d . . . H7 H 0.8287 0.0840 0.7346 0.043 Uiso 1 1 calc R . . C8 C 0.70888(19) 0.2087(3) 0.71880(8) 0.0338(6) Uani 1 1 d . . . H8 H 0.6585 0.1504 0.7301 0.041 Uiso 1 1 calc R . . C9 C 0.99628(18) 0.2189(3) 0.71223(8) 0.0323(6) Uani 1 1 d . . . C10 C 1.06964(19) 0.3246(3) 0.71511(8) 0.0349(6) Uani 1 1 d . . . H10 H 1.0505 0.4206 0.7117 0.042 Uiso 1 1 calc R . . C11 C 1.17073(19) 0.2897(3) 0.72291(8) 0.0366(6) Uani 1 1 d . . . H11 H 1.2191 0.3641 0.7248 0.044 Uiso 1 1 calc R . . C12 C 1.1335(2) 0.0578(3) 0.72457(9) 0.0423(7) Uani 1 1 d . . . H12 H 1.1551 -0.0373 0.7276 0.051 Uiso 1 1 calc R . . C13 C 1.0315(2) 0.0817(3) 0.71696(9) 0.0384(7) Uani 1 1 d . . . H13 H 0.9853 0.0047 0.7150 0.046 Uiso 1 1 calc R . . C14 C 0.52460(18) 0.3841(3) 0.73857(8) 0.0296(6) Uani 1 1 d . . . C15 C 0.57877(18) 0.4540(3) 0.76864(8) 0.0333(6) Uani 1 1 d . . . H15 H 0.6402 0.5019 0.7627 0.040 Uiso 1 1 calc R . . C16 C 0.54477(19) 0.4547(3) 0.80638(8) 0.0331(6) Uani 1 1 d . . . H16 H 0.5822 0.5044 0.8261 0.040 Uiso 1 1 calc R . . C17 C 0.45548(18) 0.3828(3) 0.81625(8) 0.0306(6) Uani 1 1 d . . . C18 C 0.40056(18) 0.3159(3) 0.78613(8) 0.0319(6) Uani 1 1 d . . . H18 H 0.3387 0.2690 0.7920 0.038 Uiso 1 1 calc R . . C19 C 0.43447(18) 0.3167(3) 0.74800(8) 0.0300(6) Uani 1 1 d . . . H19 H 0.3956 0.2706 0.7280 0.036 Uiso 1 1 calc R . . C20 C 0.42503(19) 0.3709(3) 0.85765(8) 0.0331(6) Uani 1 1 d . . . C21 C 0.4969(2) 0.3764(3) 0.88822(8) 0.0395(7) Uani 1 1 d . . . H21 H 0.5669 0.3906 0.8828 0.047 Uiso 1 1 calc R . . C22 C 0.4656(2) 0.3611(3) 0.92653(9) 0.0465(7) Uani 1 1 d . . . H22 H 0.5160 0.3657 0.9469 0.056 Uiso 1 1 calc R . . C23 C 0.3002(2) 0.3359(3) 0.90708(9) 0.0482(8) Uani 1 1 d . . . H23 H 0.2307 0.3216 0.9133 0.058 Uiso 1 1 calc R . . C24 C 0.3241(2) 0.3508(3) 0.86823(9) 0.0426(7) Uani 1 1 d . . . H24 H 0.2718 0.3474 0.8486 0.051 Uiso 1 1 calc R . . C25 C 0.41077(19) 0.4536(3) 0.66274(7) 0.0311(6) Uani 1 1 d . . . C26 C 0.38155(19) 0.5793(3) 0.68055(8) 0.0340(6) Uani 1 1 d . . . H26 H 0.4293 0.6300 0.6964 0.041 Uiso 1 1 calc R . . C27 C 0.28327(19) 0.6310(3) 0.67523(8) 0.0355(6) Uani 1 1 d . . . H27 H 0.2650 0.7176 0.6872 0.043 Uiso 1 1 calc R . . C28 C 0.21107(19) 0.5587(3) 0.65278(8) 0.0343(6) Uani 1 1 d . . . C29 C 0.2401(2) 0.4317(3) 0.63562(8) 0.0377(6) Uani 1 1 d . . . H29 H 0.1917 0.3793 0.6205 0.045 Uiso 1 1 calc R . . C30 C 0.33817(19) 0.3812(3) 0.64030(8) 0.0378(6) Uani 1 1 d . . . H30 H 0.3565 0.2953 0.6279 0.045 Uiso 1 1 calc R . . C31 C 0.1053(2) 0.6123(3) 0.64745(8) 0.0377(6) Uani 1 1 d . . . C32 C 0.0573(2) 0.6883(3) 0.67657(9) 0.0410(7) Uani 1 1 d . . . H32 H 0.0932 0.7118 0.7001 0.049 Uiso 1 1 calc R . . C33 C -0.0432(2) 0.7298(3) 0.67109(11) 0.0496(8) Uani 1 1 d . . . H33 H -0.0746 0.7795 0.6918 0.059 Uiso 1 1 calc R . . C34 C -0.0518(2) 0.6344(5) 0.61097(11) 0.0654(10) Uani 1 1 d . . . H34 H -0.0890 0.6157 0.5874 0.079 Uiso 1 1 calc R . . C35 C 0.0482(2) 0.5854(4) 0.61366(9) 0.0554(9) Uani 1 1 d . . . H35 H 0.0768 0.5342 0.5926 0.066 Uiso 1 1 calc R . . C36 C 0.56406(19) 0.3750(3) 0.62622(8) 0.0327(6) Uani 1 1 d . . . C37 C 0.5665(2) 0.4812(3) 0.59807(8) 0.0438(7) Uani 1 1 d . . . H37 H 0.5392 0.5713 0.6041 0.053 Uiso 1 1 calc R . . C38 C 0.6076(2) 0.4582(3) 0.56157(9) 0.0483(8) Uani 1 1 d . . . H38 H 0.6097 0.5332 0.5431 0.058 Uiso 1 1 calc R . . C39 C 0.6458(2) 0.3273(3) 0.55165(8) 0.0408(7) Uani 1 1 d . . . C40 C 0.6439(2) 0.2213(3) 0.57993(8) 0.0433(7) Uani 1 1 d . . . H40 H 0.6704 0.1308 0.5739 0.052 Uiso 1 1 calc R . . C41 C 0.6045(2) 0.2451(3) 0.61620(8) 0.0400(7) Uani 1 1 d . . . H41 H 0.6048 0.1709 0.6349 0.048 Uiso 1 1 calc R . . C42 C 0.6846(2) 0.2983(3) 0.51162(9) 0.0476(8) Uani 1 1 d . . . C43 C 0.6548(3) 0.3760(4) 0.47947(10) 0.0598(9) Uani 1 1 d . . . H43 H 0.6106 0.4544 0.4825 0.072 Uiso 1 1 calc R . . C44 C 0.6890(3) 0.3403(4) 0.44264(11) 0.0662(10) Uani 1 1 d . . . H44 H 0.6667 0.3964 0.4210 0.079 Uiso 1 1 calc R . . C45 C 0.7784(4) 0.1600(6) 0.46636(12) 0.115(2) Uani 1 1 d . . . H45 H 0.8223 0.0818 0.4624 0.138 Uiso 1 1 calc R . . C46 C 0.7490(4) 0.1879(6) 0.50412(12) 0.114(2) Uani 1 1 d . . . H46 H 0.7734 0.1304 0.5251 0.137 Uiso 1 1 calc R . . C47 C 0.1665(4) 0.0342(6) 0.62274(14) 0.113(2) Uani 1 1 d . . . H47A H 0.1865 0.0912 0.6002 0.169 Uiso 1 1 calc R . . H47B H 0.1546 0.0959 0.6453 0.169 Uiso 1 1 calc R . . H47C H 0.1038 -0.0176 0.6162 0.169 Uiso 1 1 calc R . . C48 C 0.3838(4) 0.1914(7) 0.53710(14) 0.1122(19) Uani 1 1 d . . . H48A H 0.4260 0.1184 0.5252 0.168 Uiso 1 1 calc R . . H48C H 0.3526 0.1539 0.5608 0.168 Uiso 1 1 calc R . . H48B H 0.4263 0.2730 0.5440 0.168 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 O1 0.090(2) 0.122(3) 0.081(2) -0.0254(19) -0.0152(17) 0.031(2) O2 0.130(3) 0.181(4) 0.0575(19) -0.017(2) 0.0016(19) 0.080(3) N1 0.0267(11) 0.0431(14) 0.0508(15) 0.0004(11) 0.0001(10) 0.0041(10) N2 0.0563(16) 0.0505(16) 0.0384(14) -0.0029(12) 0.0064(12) -0.0170(13) N3 0.0333(13) 0.0612(18) 0.072(2) 0.0069(15) -0.0010(14) 0.0126(13) N4 0.074(2) 0.084(2) 0.0420(16) -0.0012(15) 0.0114(15) 0.0247(18) C1 0.0230(12) 0.0330(14) 0.0395(15) 0.0021(12) 0.0025(11) 0.0047(11) C2 0.0251(13) 0.0289(13) 0.0396(15) 0.0026(11) 0.0005(11) -0.0021(10) C3 0.0232(12) 0.0352(14) 0.0341(14) 0.0008(11) 0.0011(10) 0.0014(11) C4 0.0298(13) 0.0330(14) 0.0384(15) 0.0065(12) 0.0002(11) 0.0011(11) C5 0.0253(13) 0.0381(15) 0.0404(15) 0.0069(12) 0.0040(11) -0.0017(11) C6 0.0250(13) 0.0351(14) 0.0341(14) 0.0008(11) 0.0029(11) 0.0025(11) C7 0.0283(13) 0.0337(14) 0.0444(16) 0.0064(12) 0.0008(12) 0.0038(11) C8 0.0247(13) 0.0368(15) 0.0399(15) 0.0071(12) 0.0023(11) -0.0016(11) C9 0.0250(13) 0.0361(14) 0.0358(14) 0.0014(12) 0.0027(11) 0.0018(11) C10 0.0248(13) 0.0346(14) 0.0456(16) 0.0025(12) 0.0028(11) 0.0021(11) C11 0.0263(13) 0.0347(15) 0.0488(17) 0.0008(13) 0.0009(12) -0.0016(11) C12 0.0298(14) 0.0349(15) 0.062(2) -0.0009(14) -0.0006(13) 0.0041(12) C13 0.0293(14) 0.0326(15) 0.0533(18) 0.0016(13) -0.0002(12) 0.0012(11) C14 0.0209(12) 0.0322(14) 0.0354(14) 0.0036(11) -0.0027(10) 0.0041(10) C15 0.0224(12) 0.0360(14) 0.0415(16) 0.0038(12) 0.0012(11) -0.0026(11) C16 0.0258(13) 0.0340(14) 0.0396(15) -0.0031(12) -0.0006(11) -0.0030(11) C17 0.0254(12) 0.0309(14) 0.0355(14) 0.0027(11) -0.0001(11) 0.0016(11) C18 0.0208(12) 0.0332(14) 0.0417(15) 0.0012(12) 0.0006(11) -0.0036(10) C19 0.0256(12) 0.0304(13) 0.0339(14) -0.0002(11) -0.0036(11) 0.0014(10) C20 0.0335(14) 0.0303(14) 0.0356(15) 0.0001(11) 0.0007(11) -0.0033(11) C21 0.0388(15) 0.0425(16) 0.0372(16) 0.0000(13) 0.0001(12) -0.0071(13) C22 0.0503(18) 0.0488(18) 0.0405(17) -0.0028(14) -0.0010(14) -0.0091(14) C23 0.0426(17) 0.057(2) 0.0452(18) -0.0054(15) 0.0077(14) -0.0199(15) C24 0.0341(15) 0.0530(18) 0.0407(17) -0.0040(14) 0.0027(12) -0.0105(13) C25 0.0286(13) 0.0356(14) 0.0293(14) 0.0023(11) 0.0026(11) 0.0040(11) C26 0.0267(13) 0.0384(15) 0.0368(15) 0.0017(12) -0.0012(11) 0.0000(11) C27 0.0290(13) 0.0362(15) 0.0412(16) 0.0010(12) 0.0022(11) 0.0052(11) C28 0.0242(13) 0.0449(16) 0.0338(14) 0.0046(12) 0.0001(11) 0.0048(11) C29 0.0275(13) 0.0480(17) 0.0375(15) -0.0062(13) -0.0052(11) 0.0008(12) C30 0.0303(14) 0.0459(16) 0.0373(15) -0.0072(13) -0.0012(11) 0.0064(12) C31 0.0296(14) 0.0438(16) 0.0397(16) 0.0091(13) 0.0023(12) 0.0043(12) C32 0.0315(14) 0.0351(15) 0.0563(19) 0.0005(13) -0.0006(13) 0.0029(12) C33 0.0360(16) 0.0412(17) 0.072(2) -0.0035(16) 0.0065(15) 0.0063(13) C34 0.0389(17) 0.100(3) 0.058(2) 0.010(2) -0.0095(16) 0.0159(19) C35 0.0383(17) 0.087(3) 0.0409(18) 0.0014(17) -0.0041(14) 0.0167(17) C36 0.0266(13) 0.0354(14) 0.0360(15) 0.0009(12) -0.0014(11) 0.0043(11) C37 0.0549(18) 0.0384(16) 0.0384(16) 0.0030(13) 0.0069(14) 0.0165(14) C38 0.061(2) 0.0440(17) 0.0406(17) 0.0070(14) 0.0089(15) 0.0161(15) C39 0.0381(15) 0.0479(17) 0.0364(16) -0.0010(13) 0.0018(12) 0.0106(13) C40 0.0521(18) 0.0377(16) 0.0402(16) -0.0007(13) 0.0046(14) 0.0147(14) C41 0.0464(16) 0.0331(15) 0.0404(16) 0.0048(12) -0.0003(13) 0.0064(12) C42 0.0486(18) 0.0540(19) 0.0406(17) -0.0001(15) 0.0070(14) 0.0137(15) C43 0.078(2) 0.051(2) 0.051(2) 0.0090(16) 0.0223(18) 0.0171(18) C44 0.089(3) 0.063(2) 0.047(2) 0.0067(17) 0.0183(19) 0.012(2) C45 0.158(5) 0.137(4) 0.051(3) -0.005(3) 0.014(3) 0.103(4) C46 0.170(5) 0.131(4) 0.041(2) 0.000(2) 0.012(3) 0.106(4) C47 0.149(5) 0.128(5) 0.061(3) 0.000(3) 0.012(3) 0.067(4) C48 0.121(4) 0.155(5) 0.060(3) -0.007(3) -0.020(3) 0.007(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C47 1.359(5) . ? O1 H1 0.8400 . ? O2 C48 1.360(5) . ? O2 H2 0.8400 . ? N1 C12 1.330(4) . ? N1 C11 1.334(4) . ? N2 C23 1.339(4) . ? N2 C22 1.339(4) . ? N3 C34 1.319(5) . ? N3 C33 1.333(4) . ? N4 C45 1.311(5) . ? N4 C44 1.317(5) . ? C1 C2 1.352(4) . ? C1 C36 1.480(4) . ? C1 C25 1.498(3) . ? C2 C14 1.485(4) . ? C2 C3 1.494(3) . ? C3 C8 1.393(4) . ? C3 C4 1.396(4) . ? C4 C5 1.384(4) . ? C4 H4 0.9500 . ? C5 C6 1.390(4) . ? C5 H5 0.9500 . ? C6 C7 1.394(4) . ? C6 C9 1.486(3) . ? C7 C8 1.387(4) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C13 1.389(4) . ? C9 C10 1.392(4) . ? C10 C11 1.388(4) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.378(4) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C19 1.387(3) . ? C14 C15 1.403(4) . ? C15 C16 1.369(4) . ? C15 H15 0.9500 . ? C16 C17 1.402(3) . ? C16 H16 0.9500 . ? C17 C18 1.396(4) . ? C17 C20 1.478(4) . ? C18 C19 1.382(4) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C24 1.392(4) . ? C20 C21 1.393(4) . ? C21 C22 1.384(4) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.374(4) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C30 1.391(4) . ? C25 C26 1.396(4) . ? C26 C27 1.388(4) . ? C26 H26 0.9500 . ? C27 C28 1.387(4) . ? C27 H27 0.9500 . ? C28 C29 1.395(4) . ? C28 C31 1.485(4) . ? C29 C30 1.379(4) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C31 C35 1.386(4) . ? C31 C32 1.387(4) . ? C32 C33 1.385(4) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C34 C35 1.392(4) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? C36 C41 1.387(4) . ? C36 C37 1.392(4) . ? C37 C38 1.383(4) . ? C37 H37 0.9500 . ? C38 C39 1.383(4) . ? C38 H38 0.9500 . ? C39 C40 1.394(4) . ? C39 C42 1.490(4) . ? C40 C41 1.368(4) . ? C40 H40 0.9500 . ? C41 H41 0.9500 . ? C42 C43 1.371(4) . ? C42 C46 1.373(5) . ? C43 C44 1.383(5) . ? C43 H43 0.9500 . ? C44 H44 0.9500 . ? C45 C46 1.376(5) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 0.9800 . ? C48 H48A 0.9800 . ? C48 H48C 0.9800 . ? C48 H48B 0.9800 . ? 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 C47 O1 H1 109.5 . . ? C48 O2 H2 109.5 . . ? C12 N1 C11 115.6(2) . . ? C23 N2 C22 115.9(3) . . ? C34 N3 C33 115.4(3) . . ? C45 N4 C44 115.1(3) . . ? C2 C1 C36 122.2(2) . . ? C2 C1 C25 123.7(2) . . ? C36 C1 C25 114.1(2) . . ? C1 C2 C14 124.8(2) . . ? C1 C2 C3 121.5(2) . . ? C14 C2 C3 113.7(2) . . ? C8 C3 C4 117.6(2) . . ? C8 C3 C2 119.8(2) . . ? C4 C3 C2 122.6(2) . . ? C5 C4 C3 121.0(2) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 121.5(2) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C5 C6 C7 117.7(2) . . ? C5 C6 C9 121.2(2) . . ? C7 C6 C9 121.0(2) . . ? C8 C7 C6 120.9(2) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C3 121.3(2) . . ? C7 C8 H8 119.3 . . ? C3 C8 H8 119.3 . . ? C13 C9 C10 116.0(2) . . ? C13 C9 C6 122.8(2) . . ? C10 C9 C6 121.1(2) . . ? C11 C10 C9 119.9(3) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? N1 C11 C10 123.9(3) . . ? N1 C11 H11 118.0 . . ? C10 C11 H11 118.0 . . ? N1 C12 C13 124.8(3) . . ? N1 C12 H12 117.6 . . ? C13 C12 H12 117.6 . . ? C12 C13 C9 119.7(3) . . ? C12 C13 H13 120.1 . . ? C9 C13 H13 120.1 . . ? C19 C14 C15 118.1(2) . . ? C19 C14 C2 122.6(2) . . ? C15 C14 C2 119.1(2) . . ? C16 C15 C14 121.3(2) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C17 120.8(2) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C18 C17 C16 117.8(2) . . ? C18 C17 C20 121.5(2) . . ? C16 C17 C20 120.6(2) . . ? C19 C18 C17 121.2(2) . . ? C19 C18 H18 119.4 . . ? C17 C18 H18 119.4 . . ? C18 C19 C14 120.8(2) . . ? C18 C19 H19 119.6 . . ? C14 C19 H19 119.6 . . ? C24 C20 C21 116.4(3) . . ? C24 C20 C17 122.2(2) . . ? C21 C20 C17 121.3(2) . . ? C22 C21 C20 119.5(3) . . ? C22 C21 H21 120.2 . . ? C20 C21 H21 120.2 . . ? N2 C22 C21 124.0(3) . . ? N2 C22 H22 118.0 . . ? C21 C22 H22 118.0 . . ? N2 C23 C24 124.1(3) . . ? N2 C23 H23 117.9 . . ? C24 C23 H23 117.9 . . ? C23 C24 C20 119.9(3) . . ? C23 C24 H24 120.0 . . ? C20 C24 H24 120.0 . . ? C30 C25 C26 118.0(2) . . ? C30 C25 C1 119.7(2) . . ? C26 C25 C1 122.1(2) . . ? C27 C26 C25 120.5(3) . . ? C27 C26 H26 119.8 . . ? C25 C26 H26 119.8 . . ? C28 C27 C26 121.4(3) . . ? C28 C27 H27 119.3 . . ? C26 C27 H27 119.3 . . ? C27 C28 C29 118.0(2) . . ? C27 C28 C31 121.6(3) . . ? C29 C28 C31 120.4(2) . . ? C30 C29 C28 120.8(3) . . ? C30 C29 H29 119.6 . . ? C28 C29 H29 119.6 . . ? C29 C30 C25 121.3(3) . . ? C29 C30 H30 119.3 . . ? C25 C30 H30 119.3 . . ? C35 C31 C32 116.4(3) . . ? C35 C31 C28 121.9(3) . . ? C32 C31 C28 121.7(3) . . ? C33 C32 C31 119.6(3) . . ? C33 C32 H32 120.2 . . ? C31 C32 H32 120.2 . . ? N3 C33 C32 124.4(3) . . ? N3 C33 H33 117.8 . . ? C32 C33 H33 117.8 . . ? N3 C34 C35 125.0(3) . . ? N3 C34 H34 117.5 . . ? C35 C34 H34 117.5 . . ? C31 C35 C34 119.2(3) . . ? C31 C35 H35 120.4 . . ? C34 C35 H35 120.4 . . ? C41 C36 C37 117.3(3) . . ? C41 C36 C1 121.9(2) . . ? C37 C36 C1 120.8(2) . . ? C38 C37 C36 121.4(3) . . ? C38 C37 H37 119.3 . . ? C36 C37 H37 119.3 . . ? C37 C38 C39 120.7(3) . . ? C37 C38 H38 119.7 . . ? C39 C38 H38 119.7 . . ? C38 C39 C40 117.9(3) . . ? C38 C39 C42 121.4(3) . . ? C40 C39 C42 120.7(3) . . ? C41 C40 C39 121.2(3) . . ? C41 C40 H40 119.4 . . ? C39 C40 H40 119.4 . . ? C40 C41 C36 121.5(3) . . ? C40 C41 H41 119.3 . . ? C36 C41 H41 119.3 . . ? C43 C42 C46 115.3(3) . . ? C43 C42 C39 122.4(3) . . ? C46 C42 C39 122.2(3) . . ? C42 C43 C44 120.1(3) . . ? C42 C43 H43 119.9 . . ? C44 C43 H43 119.9 . . ? N4 C44 C43 124.4(3) . . ? N4 C44 H44 117.8 . . ? C43 C44 H44 117.8 . . ? N4 C45 C46 124.6(4) . . ? N4 C45 H45 117.7 . . ? C46 C45 H45 117.7 . . ? C42 C46 C45 120.3(4) . . ? C42 C46 H46 119.8 . . ? C45 C46 H46 119.8 . . ? O1 C47 H47A 109.5 . . ? O1 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? O1 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? O2 C48 H48A 109.5 . . ? O2 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? O2 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? H48C C48 H48B 109.5 . . ? 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 C36 C1 C2 C14 -173.3(2) . . . . ? C25 C1 C2 C14 5.5(4) . . . . ? C36 C1 C2 C3 5.7(4) . . . . ? C25 C1 C2 C3 -175.5(2) . . . . ? C1 C2 C3 C8 -124.9(3) . . . . ? C14 C2 C3 C8 54.2(3) . . . . ? C1 C2 C3 C4 57.3(4) . . . . ? C14 C2 C3 C4 -123.6(3) . . . . ? C8 C3 C4 C5 -2.0(4) . . . . ? C2 C3 C4 C5 175.8(3) . . . . ? C3 C4 C5 C6 0.6(4) . . . . ? C4 C5 C6 C7 1.5(4) . . . . ? C4 C5 C6 C9 -174.7(3) . . . . ? C5 C6 C7 C8 -2.3(4) . . . . ? C9 C6 C7 C8 174.0(3) . . . . ? C6 C7 C8 C3 0.9(4) . . . . ? C4 C3 C8 C7 1.2(4) . . . . ? C2 C3 C8 C7 -176.7(3) . . . . ? C5 C6 C9 C13 -153.4(3) . . . . ? C7 C6 C9 C13 30.5(4) . . . . ? C5 C6 C9 C10 28.8(4) . . . . ? C7 C6 C9 C10 -147.3(3) . . . . ? C13 C9 C10 C11 -1.0(4) . . . . ? C6 C9 C10 C11 176.9(2) . . . . ? C12 N1 C11 C10 0.7(4) . . . . ? C9 C10 C11 N1 0.2(4) . . . . ? C11 N1 C12 C13 -0.8(4) . . . . ? N1 C12 C13 C9 0.0(5) . . . . ? C10 C9 C13 C12 0.9(4) . . . . ? C6 C9 C13 C12 -177.0(3) . . . . ? C1 C2 C14 C19 50.6(4) . . . . ? C3 C2 C14 C19 -128.4(3) . . . . ? C1 C2 C14 C15 -134.5(3) . . . . ? C3 C2 C14 C15 46.5(3) . . . . ? C19 C14 C15 C16 0.8(4) . . . . ? C2 C14 C15 C16 -174.3(2) . . . . ? C14 C15 C16 C17 1.3(4) . . . . ? C15 C16 C17 C18 -2.6(4) . . . . ? C15 C16 C17 C20 173.4(2) . . . . ? C16 C17 C18 C19 1.9(4) . . . . ? C20 C17 C18 C19 -174.0(2) . . . . ? C17 C18 C19 C14 0.2(4) . . . . ? C15 C14 C19 C18 -1.5(4) . . . . ? C2 C14 C19 C18 173.4(2) . . . . ? C18 C17 C20 C24 -29.0(4) . . . . ? C16 C17 C20 C24 155.1(3) . . . . ? C18 C17 C20 C21 149.7(3) . . . . ? C16 C17 C20 C21 -26.2(4) . . . . ? C24 C20 C21 C22 0.4(4) . . . . ? C17 C20 C21 C22 -178.3(3) . . . . ? C23 N2 C22 C21 -0.5(5) . . . . ? C20 C21 C22 N2 0.2(5) . . . . ? C22 N2 C23 C24 0.2(5) . . . . ? N2 C23 C24 C20 0.5(5) . . . . ? C21 C20 C24 C23 -0.8(4) . . . . ? C17 C20 C24 C23 178.0(3) . . . . ? C2 C1 C25 C30 -126.9(3) . . . . ? C36 C1 C25 C30 52.0(3) . . . . ? C2 C1 C25 C26 57.3(4) . . . . ? C36 C1 C25 C26 -123.8(3) . . . . ? C30 C25 C26 C27 -1.1(4) . . . . ? C1 C25 C26 C27 174.8(2) . . . . ? C25 C26 C27 C28 1.1(4) . . . . ? C26 C27 C28 C29 0.1(4) . . . . ? C26 C27 C28 C31 179.1(3) . . . . ? C27 C28 C29 C30 -1.2(4) . . . . ? C31 C28 C29 C30 179.8(3) . . . . ? C28 C29 C30 C25 1.1(4) . . . . ? C26 C25 C30 C29 0.1(4) . . . . ? C1 C25 C30 C29 -175.9(3) . . . . ? C27 C28 C31 C35 149.8(3) . . . . ? C29 C28 C31 C35 -31.2(4) . . . . ? C27 C28 C31 C32 -32.2(4) . . . . ? C29 C28 C31 C32 146.8(3) . . . . ? C35 C31 C32 C33 1.4(4) . . . . ? C28 C31 C32 C33 -176.6(3) . . . . ? C34 N3 C33 C32 0.6(5) . . . . ? C31 C32 C33 N3 -1.7(5) . . . . ? C33 N3 C34 C35 0.7(6) . . . . ? C32 C31 C35 C34 -0.3(5) . . . . ? C28 C31 C35 C34 177.8(3) . . . . ? N3 C34 C35 C31 -0.9(6) . . . . ? C2 C1 C36 C41 54.8(4) . . . . ? C25 C1 C36 C41 -124.1(3) . . . . ? C2 C1 C36 C37 -126.3(3) . . . . ? C25 C1 C36 C37 54.8(3) . . . . ? C41 C36 C37 C38 -0.1(4) . . . . ? C1 C36 C37 C38 -179.0(3) . . . . ? C36 C37 C38 C39 1.4(5) . . . . ? C37 C38 C39 C40 -1.7(5) . . . . ? C37 C38 C39 C42 176.2(3) . . . . ? C38 C39 C40 C41 0.7(5) . . . . ? C42 C39 C40 C41 -177.2(3) . . . . ? C39 C40 C41 C36 0.6(5) . . . . ? C37 C36 C41 C40 -0.9(4) . . . . ? C1 C36 C41 C40 178.0(3) . . . . ? C38 C39 C42 C43 -22.8(5) . . . . ? C40 C39 C42 C43 155.0(3) . . . . ? C38 C39 C42 C46 160.3(4) . . . . ? C40 C39 C42 C46 -21.9(6) . . . . ? C46 C42 C43 C44 0.4(6) . . . . ? C39 C42 C43 C44 -176.7(3) . . . . ? C45 N4 C44 C43 0.1(7) . . . . ? C42 C43 C44 N4 -0.1(7) . . . . ? C44 N4 C45 C46 -0.5(9) . . . . ? C43 C42 C46 C45 -0.8(8) . . . . ? C39 C42 C46 C45 176.3(5) . . . . ? N4 C45 C46 C42 0.9(11) . . . . ? 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 H1 N4 0.84 2.00 2.837(4) 171.0 3_656 O2 H2 N2 0.84 1.93 2.756(4) 169.5 4_565 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.377 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.045 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 0.000 -0.033 0.000 345 72 ' ' 2 0.000 -0.059 0.500 345 72 ' '