Supplementary Material (ESI) for Analyst This journal is (C) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 91 loop_ _publ_author_name 'Juyoung Yoon' _publ_contact_author_name 'Juyoung Yoon' _publ_contact_author_address ; 11-1 Daehyon-Dong, Sodaemun-Ku Seoul 120-750 ; _publ_contact_author_email jyoon@ewha.ac.kr data_SW279 _database_code_depnum_ccdc_archive 'CCDC 806060' #TrackingRef 'SW279.cif' _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H26 N4 O4' _chemical_formula_weight 578.61 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 9.230(2) _cell_length_b 12.017(3) _cell_length_c 14.264(4) _cell_angle_alpha 80.136(5) _cell_angle_beta 84.480(5) _cell_angle_gamma 87.213(5) _cell_volume 1550.7(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 745 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 21.56 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.992 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_process_details '(SADABS; Bruker, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8519 _diffrn_reflns_av_R_equivalents 0.0507 _diffrn_reflns_av_sigmaI/netI 0.1777 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5840 _reflns_number_gt 1806 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1115P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5840 _refine_ls_number_parameters 398 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.1892 _refine_ls_R_factor_gt 0.0682 _refine_ls_wR_factor_ref 0.2154 _refine_ls_wR_factor_gt 0.1705 _refine_ls_goodness_of_fit_ref 0.856 _refine_ls_restrained_S_all 0.855 _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 C1 C 0.9190(4) 0.4446(4) 0.1661(3) 0.0516(11) Uani 1 1 d . . . C2 C 0.9296(4) 0.3297(4) 0.1940(3) 0.0654(13) Uani 1 1 d . . . H2 H 0.8985 0.2831 0.1546 0.079 Uiso 1 1 calc R . . C3 C 0.9850(4) 0.2807(4) 0.2787(3) 0.0600(12) Uani 1 1 d . A . C4 C 1.0319(4) 0.3540(4) 0.3351(3) 0.0583(12) Uani 1 1 d . . . H4 H 1.0696 0.3250 0.3928 0.070 Uiso 1 1 calc R . . C5 C 1.0223(4) 0.4704(4) 0.3049(3) 0.0586(12) Uani 1 1 d . . . H5 H 1.0548 0.5175 0.3433 0.070 Uiso 1 1 calc R . . C6 C 0.9664(4) 0.5193(4) 0.2200(3) 0.0457(10) Uani 1 1 d . . . C7 C 0.9597(4) 0.6437(3) 0.1892(3) 0.0465(10) Uani 1 1 d . . . C8 C 0.8768(4) 0.6756(4) 0.1027(3) 0.0468(10) Uani 1 1 d . . . C9 C 0.8383(4) 0.7865(4) 0.0670(3) 0.0658(13) Uani 1 1 d . . . H9 H 0.8696 0.8434 0.0962 0.079 Uiso 1 1 calc R . . C10 C 0.7564(4) 0.8170(4) -0.0093(3) 0.0687(14) Uani 1 1 d . . . H10 H 0.7320 0.8928 -0.0292 0.082 Uiso 1 1 calc R . . C11 C 0.7098(4) 0.7365(4) -0.0566(3) 0.0572(12) Uani 1 1 d . B . C12 C 0.7488(4) 0.6239(4) -0.0218(3) 0.0646(13) Uani 1 1 d . . . H12 H 0.7200 0.5665 -0.0515 0.077 Uiso 1 1 calc R . . C13 C 0.8288(4) 0.5975(4) 0.0554(3) 0.0526(11) Uani 1 1 d . . . C14 C 1.0344(5) 0.1143(4) 0.4009(3) 0.0778(15) Uani 1 1 d . A . H14A H 0.9896 0.0415 0.4190 0.093 Uiso 1 1 calc R . . H14B H 0.9958 0.1616 0.4468 0.093 Uiso 1 1 calc R . . C15 C 1.1961(5) 0.0976(5) 0.4070(4) 0.107(2) Uani 1 1 d . . . H15A H 1.2367 0.0555 0.3588 0.160 Uiso 1 1 calc R . . H15B H 1.2145 0.0569 0.4689 0.160 Uiso 1 1 calc R . . H15C H 1.2402 0.1699 0.3971 0.160 Uiso 1 1 calc R . . C16 C 0.9868(6) 0.0853(5) 0.2345(4) 0.073(3) Uiso 0.665(11) 1 d PD A 1 C17 C 0.8271(6) 0.0500(8) 0.2528(6) 0.102(3) Uiso 0.665(11) 1 d PD A 1 C16* C 0.8804(10) 0.0965(10) 0.2708(8) 0.066(5) Uiso 0.335(11) 1 d PD A 2 C17* C 0.9576(15) 0.0560(13) 0.1815(9) 0.086(6) Uiso 0.335(11) 1 d PD A 2 C18 C 0.5747(5) 0.8783(5) -0.1653(3) 0.0854(16) Uani 1 1 d . B . H18A H 0.5448 0.8848 -0.2294 0.102 Uiso 1 1 calc R . . H18B H 0.6538 0.9294 -0.1678 0.102 Uiso 1 1 calc R . . C19 C 0.4465(6) 0.9151(5) -0.0999(4) 0.112(2) Uani 1 1 d . . . H19A H 0.3697 0.8627 -0.0942 0.168 Uiso 1 1 calc R . . H19B H 0.4116 0.9892 -0.1265 0.168 Uiso 1 1 calc R . . H19C H 0.4780 0.9165 -0.0379 0.168 Uiso 1 1 calc R . . C20 C 0.6052(6) 0.6743(5) -0.1973(4) 0.079(3) Uiso 0.774(12) 1 d PD B 1 C21 C 0.4685(6) 0.6121(7) -0.1491(6) 0.106(3) Uiso 0.774(12) 1 d PD B 1 C20* C 0.4988(13) 0.6883(13) -0.1393(13) 0.067(8) Uiso 0.226(12) 1 d PD B 2 C21* C 0.525(3) 0.612(2) -0.2160(16) 0.117(11) Uiso 0.226(12) 1 d PD B 2 C22 C 1.1110(4) 0.6947(4) 0.1780(3) 0.0494(11) Uani 1 1 d . . . C23 C 1.2276(4) 0.6756(4) 0.1119(3) 0.0619(12) Uani 1 1 d . . . H23 H 1.2173 0.6332 0.0643 0.074 Uiso 1 1 calc R . . C24 C 1.3581(5) 0.7220(4) 0.1200(4) 0.0710(14) Uani 1 1 d . . . H24 H 1.4375 0.7104 0.0770 0.085 Uiso 1 1 calc R . . C25 C 1.3745(5) 0.7849(5) 0.1898(4) 0.0773(15) Uani 1 1 d . . . H25 H 1.4652 0.8135 0.1938 0.093 Uiso 1 1 calc R . . C26 C 1.2588(4) 0.8070(4) 0.2546(3) 0.0654(13) Uani 1 1 d . . . H26 H 1.2677 0.8524 0.3003 0.078 Uiso 1 1 calc R . . C27 C 1.1278(4) 0.7564(4) 0.2469(3) 0.0519(11) Uani 1 1 d . . . C28 C 0.9876(4) 0.7618(4) 0.3085(3) 0.0496(11) Uani 1 1 d . . . C29 C 0.6826(4) 0.7194(3) 0.3668(2) 0.0563(12) Uani 1 1 d D . . H29 H 0.7211 0.7784 0.3898 0.068 Uiso 1 1 calc R . . C30 C 0.5361(4) 0.6763(4) 0.4016(3) 0.0589(13) Uani 1 1 d . . . C31 C 0.4424(4) 0.7337(4) 0.4629(3) 0.0550(12) Uani 1 1 d . . . C32 C 0.3111(5) 0.6863(5) 0.5031(3) 0.0719(14) Uani 1 1 d . . . H32 H 0.2520 0.7222 0.5462 0.086 Uiso 1 1 calc R . . C33 C 0.2678(5) 0.5873(5) 0.4799(3) 0.0767(15) Uani 1 1 d . . . H33 H 0.1793 0.5571 0.5065 0.092 Uiso 1 1 calc R . . C34 C 0.3570(5) 0.5325(4) 0.4165(3) 0.0742(14) Uani 1 1 d . . . H34 H 0.3282 0.4663 0.3991 0.089 Uiso 1 1 calc R . . C35 C 0.4901(5) 0.5787(4) 0.3796(3) 0.0672(13) Uani 1 1 d . . . H35 H 0.5503 0.5414 0.3381 0.081 Uiso 1 1 calc R . . C36 C 0.4720(4) 0.8455(5) 0.4800(3) 0.0624(13) Uani 1 1 d . . . N1 N 0.9930(5) 0.1655(4) 0.3072(3) 0.0945(14) Uani 1 1 d D . . N2 N 0.6280(4) 0.7629(4) -0.1344(3) 0.0855(13) Uani 1 1 d D . . N3 N 0.8936(3) 0.7032(3) 0.2695(2) 0.0498(9) Uani 1 1 d . . . N4 N 0.7534(3) 0.6693(3) 0.3019(2) 0.0557(10) Uani 1 1 d D . . O1 O 0.8590(3) 0.4819(3) 0.08125(19) 0.0688(9) Uani 1 1 d . . . O2 O 0.9610(3) 0.8076(3) 0.3783(2) 0.0726(9) Uani 1 1 d . . . O3 O 0.5345(3) 0.9183(3) 0.4195(2) 0.0756(10) Uani 1 1 d . . . O4 O 0.4214(3) 0.8709(3) 0.5641(2) 0.0824(10) Uani 1 1 d . . . H4A H 0.4568 0.9298 0.5715 0.124 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 C1 0.056(2) 0.056(4) 0.041(2) -0.004(2) -0.008(2) 0.003(2) C2 0.084(3) 0.064(4) 0.051(3) -0.011(2) -0.018(2) -0.002(2) C3 0.063(3) 0.064(4) 0.050(3) 0.002(3) -0.012(2) -0.006(2) C4 0.054(2) 0.075(4) 0.044(2) -0.001(3) -0.008(2) 0.002(2) C5 0.051(2) 0.072(4) 0.055(3) -0.017(2) -0.009(2) 0.008(2) C6 0.038(2) 0.050(3) 0.047(2) -0.008(2) 0.0039(18) 0.0012(19) C7 0.046(2) 0.046(3) 0.050(2) -0.020(2) 0.0005(19) 0.0010(19) C8 0.044(2) 0.050(3) 0.049(2) -0.014(2) -0.0062(19) -0.0011(19) C9 0.067(3) 0.067(4) 0.068(3) -0.021(3) -0.021(2) 0.006(2) C10 0.064(3) 0.073(4) 0.068(3) -0.005(3) -0.016(2) 0.005(2) C11 0.065(3) 0.054(4) 0.054(3) -0.007(2) -0.016(2) 0.003(2) C12 0.077(3) 0.070(4) 0.046(3) -0.008(2) -0.011(2) 0.000(2) C13 0.054(2) 0.056(4) 0.044(3) 0.000(2) -0.004(2) 0.005(2) C14 0.087(3) 0.078(4) 0.063(3) 0.013(3) -0.022(3) -0.009(3) C15 0.085(4) 0.126(6) 0.104(4) -0.005(4) -0.015(3) 0.023(3) C18 0.099(4) 0.083(5) 0.074(3) -0.003(3) -0.023(3) 0.004(3) C19 0.096(4) 0.119(6) 0.120(5) -0.018(4) -0.017(4) 0.009(3) C22 0.047(2) 0.051(3) 0.048(2) -0.005(2) -0.0011(19) -0.0005(19) C23 0.057(3) 0.057(3) 0.069(3) -0.013(2) 0.008(2) 0.003(2) C24 0.054(3) 0.073(4) 0.084(3) -0.012(3) 0.009(2) -0.011(2) C25 0.047(3) 0.080(4) 0.099(4) 0.004(3) -0.003(3) -0.014(2) C26 0.062(3) 0.059(3) 0.080(3) -0.016(2) -0.020(3) -0.013(2) C27 0.053(3) 0.051(3) 0.052(3) -0.006(2) -0.013(2) -0.004(2) C28 0.048(2) 0.048(3) 0.054(3) -0.012(2) -0.008(2) 0.007(2) C29 0.045(2) 0.064(3) 0.060(3) -0.017(2) -0.003(2) 0.008(2) C30 0.038(2) 0.084(4) 0.053(3) -0.007(3) -0.004(2) 0.007(2) C31 0.041(2) 0.065(4) 0.060(3) -0.019(2) 0.000(2) 0.007(2) C32 0.055(3) 0.089(5) 0.070(3) -0.015(3) 0.003(2) 0.006(3) C33 0.050(3) 0.095(5) 0.084(3) -0.015(3) 0.002(2) -0.007(3) C34 0.059(3) 0.085(4) 0.080(3) -0.013(3) -0.009(3) -0.009(3) C35 0.052(3) 0.086(4) 0.067(3) -0.019(3) -0.009(2) -0.001(3) C36 0.050(3) 0.085(4) 0.052(3) -0.022(3) 0.006(2) 0.015(3) N1 0.158(4) 0.057(3) 0.070(3) 0.015(2) -0.055(3) -0.020(3) N2 0.106(3) 0.072(3) 0.079(3) 0.002(2) -0.042(2) 0.010(2) N3 0.0401(19) 0.059(3) 0.055(2) -0.0223(18) -0.0032(16) -0.0007(16) N4 0.0393(19) 0.078(3) 0.050(2) -0.0146(19) 0.0002(16) 0.0028(17) O1 0.094(2) 0.062(3) 0.0533(18) -0.0091(15) -0.0269(16) 0.0062(17) O2 0.0665(19) 0.095(3) 0.0651(19) -0.0404(19) -0.0063(15) 0.0055(16) O3 0.080(2) 0.073(3) 0.069(2) -0.0149(17) 0.0187(17) 0.0085(18) O4 0.085(2) 0.096(3) 0.066(2) -0.0268(19) 0.0174(17) 0.0008(19) _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 C1 C2 1.372(6) . ? C1 O1 1.376(4) . ? C1 C6 1.388(5) . ? C2 C3 1.384(5) . ? C2 H2 0.9300 . ? C3 N1 1.375(5) . ? C3 C4 1.399(6) . ? C4 C5 1.392(6) . ? C4 H4 0.9300 . ? C5 C6 1.388(5) . ? C5 H5 0.9300 . ? C6 C7 1.484(5) . ? C7 C8 1.499(5) . ? C7 N3 1.516(5) . ? C7 C22 1.535(5) . ? C8 C13 1.359(6) . ? C8 C9 1.386(5) . ? C9 C10 1.372(5) . ? C9 H9 0.9300 . ? C10 C11 1.377(6) . ? C10 H10 0.9300 . ? C11 N2 1.385(5) . ? C11 C12 1.401(6) . ? C12 C13 1.369(5) . ? C12 H12 0.9300 . ? C13 O1 1.397(5) . ? C14 N1 1.451(5) . ? C14 C15 1.505(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 N1 1.539(2) . ? C16 C17 1.540(2) . ? C16* C17* 1.540(2) . ? C16* N1 1.540(2) . ? C18 N2 1.458(6) . ? C18 C19 1.531(6) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 N2 1.538(2) . ? C20 C21 1.541(2) . ? C20* C21* 1.540(2) . ? C20* N2 1.540(2) . ? C22 C27 1.352(5) . ? C22 C23 1.399(5) . ? C23 C24 1.374(6) . ? C23 H23 0.9300 . ? C24 C25 1.373(7) . ? C24 H24 0.9300 . ? C25 C26 1.390(6) . ? C25 H25 0.9300 . ? C26 C27 1.402(5) . ? C26 H26 0.9300 . ? C27 C28 1.497(5) . ? C28 O2 1.217(4) . ? C28 N3 1.358(5) . ? C29 N4 1.2969(19) . ? C29 C30 1.481(5) . ? C29 H29 0.9300 . ? C30 C35 1.361(6) . ? C30 C31 1.411(6) . ? C31 C32 1.394(5) . ? C31 C36 1.449(6) . ? C32 C33 1.375(6) . ? C32 H32 0.9300 . ? C33 C34 1.393(6) . ? C33 H33 0.9300 . ? C34 C35 1.392(6) . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? C36 O3 1.239(5) . ? C36 O4 1.325(5) . ? N3 N4 1.388(4) . ? O4 H4A 0.8200 . ? 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 O1 116.0(4) . . ? C2 C1 C6 122.2(4) . . ? O1 C1 C6 121.7(4) . . ? C1 C2 C3 122.1(5) . . ? C1 C2 H2 118.9 . . ? C3 C2 H2 118.9 . . ? N1 C3 C2 122.0(5) . . ? N1 C3 C4 121.1(4) . . ? C2 C3 C4 116.9(5) . . ? C5 C4 C3 120.1(4) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C6 C5 C4 122.9(4) . . ? C6 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? C1 C6 C5 115.7(4) . . ? C1 C6 C7 122.8(4) . . ? C5 C6 C7 121.5(4) . . ? C6 C7 C8 111.0(3) . . ? C6 C7 N3 111.3(3) . . ? C8 C7 N3 110.6(3) . . ? C6 C7 C22 112.0(3) . . ? C8 C7 C22 113.8(3) . . ? N3 C7 C22 97.5(3) . . ? C13 C8 C9 114.7(4) . . ? C13 C8 C7 122.6(4) . . ? C9 C8 C7 122.6(4) . . ? C10 C9 C8 123.5(5) . . ? C10 C9 H9 118.2 . . ? C8 C9 H9 118.2 . . ? C9 C10 C11 120.7(5) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C10 C11 N2 122.9(4) . . ? C10 C11 C12 116.5(4) . . ? N2 C11 C12 120.6(4) . . ? C13 C12 C11 120.7(5) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C8 C13 C12 123.9(4) . . ? C8 C13 O1 122.4(4) . . ? C12 C13 O1 113.8(4) . . ? N1 C14 C15 114.4(4) . . ? N1 C14 H14A 108.7 . . ? C15 C14 H14A 108.7 . . ? N1 C14 H14B 108.7 . . ? C15 C14 H14B 108.7 . . ? H14A C14 H14B 107.6 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N1 C16 C17 101.5(5) . . ? C17* C16* N1 105.5(8) . . ? N2 C18 C19 113.4(4) . . ? N2 C18 H18A 108.9 . . ? C19 C18 H18A 108.9 . . ? N2 C18 H18B 108.9 . . ? C19 C18 H18B 108.9 . . ? H18A C18 H18B 107.7 . . ? 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 . . ? N2 C20 C21 104.7(5) . . ? C21* C20* N2 113.7(14) . . ? C27 C22 C23 120.6(4) . . ? C27 C22 C7 112.1(3) . . ? C23 C22 C7 127.1(4) . . ? C24 C23 C22 117.4(5) . . ? C24 C23 H23 121.3 . . ? C22 C23 H23 121.3 . . ? C25 C24 C23 121.8(4) . . ? C25 C24 H24 119.1 . . ? C23 C24 H24 119.1 . . ? C24 C25 C26 121.5(4) . . ? C24 C25 H25 119.2 . . ? C26 C25 H25 119.2 . . ? C25 C26 C27 115.8(5) . . ? C25 C26 H26 122.1 . . ? C27 C26 H26 122.1 . . ? C22 C27 C26 122.8(4) . . ? C22 C27 C28 109.6(3) . . ? C26 C27 C28 127.6(4) . . ? O2 C28 N3 126.6(4) . . ? O2 C28 C27 128.8(4) . . ? N3 C28 C27 104.6(3) . . ? N4 C29 C30 115.5(4) . . ? N4 C29 H29 122.3 . . ? C30 C29 H29 122.3 . . ? C35 C30 C31 118.1(4) . . ? C35 C30 C29 121.8(4) . . ? C31 C30 C29 120.1(4) . . ? C32 C31 C30 119.6(5) . . ? C32 C31 C36 118.0(4) . . ? C30 C31 C36 122.2(4) . . ? C33 C32 C31 120.9(4) . . ? C33 C32 H32 119.5 . . ? C31 C32 H32 119.5 . . ? C32 C33 C34 119.7(5) . . ? C32 C33 H33 120.1 . . ? C34 C33 H33 120.1 . . ? C35 C34 C33 118.6(5) . . ? C35 C34 H34 120.7 . . ? C33 C34 H34 120.7 . . ? C30 C35 C34 122.9(4) . . ? C30 C35 H35 118.6 . . ? C34 C35 H35 118.6 . . ? O3 C36 O4 119.5(5) . . ? O3 C36 C31 123.8(4) . . ? O4 C36 C31 116.6(4) . . ? C3 N1 C14 122.1(4) . . ? C3 N1 C16 120.7(4) . . ? C14 N1 C16 116.3(5) . . ? C3 N1 C16* 116.6(6) . . ? C14 N1 C16* 112.4(6) . . ? C16 N1 C16* 41.0(4) . . ? C11 N2 C18 121.0(4) . . ? C11 N2 C20 120.8(4) . . ? C18 N2 C20 117.9(4) . . ? C11 N2 C20* 118.2(8) . . ? C18 N2 C20* 105.0(8) . . ? C20 N2 C20* 47.7(7) . . ? C28 N3 N4 130.7(3) . . ? C28 N3 C7 115.6(3) . . ? N4 N3 C7 112.4(3) . . ? C29 N4 N3 117.9(3) . . ? C1 O1 C13 118.4(3) . . ? C36 O4 H4A 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 O1 C1 C2 C3 -178.6(3) . . . . ? C6 C1 C2 C3 1.6(6) . . . . ? C1 C2 C3 N1 178.9(4) . . . . ? C1 C2 C3 C4 -0.7(6) . . . . ? N1 C3 C4 C5 -179.8(4) . . . . ? C2 C3 C4 C5 -0.3(5) . . . . ? C3 C4 C5 C6 0.4(5) . . . . ? C2 C1 C6 C5 -1.3(5) . . . . ? O1 C1 C6 C5 178.9(3) . . . . ? C2 C1 C6 C7 178.1(3) . . . . ? O1 C1 C6 C7 -1.7(5) . . . . ? C4 C5 C6 C1 0.3(5) . . . . ? C4 C5 C6 C7 -179.1(3) . . . . ? C1 C6 C7 C8 8.4(4) . . . . ? C5 C6 C7 C8 -172.2(3) . . . . ? C1 C6 C7 N3 132.0(3) . . . . ? C5 C6 C7 N3 -48.6(4) . . . . ? C1 C6 C7 C22 -120.0(4) . . . . ? C5 C6 C7 C22 59.4(4) . . . . ? C6 C7 C8 C13 -6.1(5) . . . . ? N3 C7 C8 C13 -130.1(4) . . . . ? C22 C7 C8 C13 121.4(4) . . . . ? C6 C7 C8 C9 171.4(3) . . . . ? N3 C7 C8 C9 47.4(5) . . . . ? C22 C7 C8 C9 -61.2(5) . . . . ? C13 C8 C9 C10 0.9(6) . . . . ? C7 C8 C9 C10 -176.7(3) . . . . ? C8 C9 C10 C11 -1.5(6) . . . . ? C9 C10 C11 N2 -179.4(4) . . . . ? C9 C10 C11 C12 0.9(6) . . . . ? C10 C11 C12 C13 0.1(6) . . . . ? N2 C11 C12 C13 -179.6(4) . . . . ? C9 C8 C13 C12 0.1(5) . . . . ? C7 C8 C13 C12 177.8(3) . . . . ? C9 C8 C13 O1 179.4(3) . . . . ? C7 C8 C13 O1 -3.0(5) . . . . ? C11 C12 C13 C8 -0.6(6) . . . . ? C11 C12 C13 O1 -179.9(3) . . . . ? C6 C7 C22 C27 -109.6(4) . . . . ? C8 C7 C22 C27 123.5(4) . . . . ? N3 C7 C22 C27 7.0(4) . . . . ? C6 C7 C22 C23 64.9(5) . . . . ? C8 C7 C22 C23 -62.0(5) . . . . ? N3 C7 C22 C23 -178.4(4) . . . . ? C27 C22 C23 C24 -0.1(6) . . . . ? C7 C22 C23 C24 -174.2(4) . . . . ? C22 C23 C24 C25 -0.1(7) . . . . ? C23 C24 C25 C26 -1.4(8) . . . . ? C24 C25 C26 C27 3.1(7) . . . . ? C23 C22 C27 C26 2.0(6) . . . . ? C7 C22 C27 C26 176.9(3) . . . . ? C23 C22 C27 C28 -179.0(3) . . . . ? C7 C22 C27 C28 -4.1(5) . . . . ? C25 C26 C27 C22 -3.4(6) . . . . ? C25 C26 C27 C28 177.8(4) . . . . ? C22 C27 C28 O2 178.6(4) . . . . ? C26 C27 C28 O2 -2.4(7) . . . . ? C22 C27 C28 N3 -1.3(4) . . . . ? C26 C27 C28 N3 177.7(4) . . . . ? N4 C29 C30 C35 11.0(6) . . . . ? N4 C29 C30 C31 -171.8(3) . . . . ? C35 C30 C31 C32 3.8(6) . . . . ? C29 C30 C31 C32 -173.4(3) . . . . ? C35 C30 C31 C36 -171.2(4) . . . . ? C29 C30 C31 C36 11.6(6) . . . . ? C30 C31 C32 C33 -3.6(6) . . . . ? C36 C31 C32 C33 171.6(4) . . . . ? C31 C32 C33 C34 0.9(7) . . . . ? C32 C33 C34 C35 1.4(7) . . . . ? C31 C30 C35 C34 -1.5(6) . . . . ? C29 C30 C35 C34 175.7(3) . . . . ? C33 C34 C35 C30 -1.1(6) . . . . ? C32 C31 C36 O3 -142.5(4) . . . . ? C30 C31 C36 O3 32.6(6) . . . . ? C32 C31 C36 O4 34.0(5) . . . . ? C30 C31 C36 O4 -151.0(4) . . . . ? C2 C3 N1 C14 -172.4(4) . . . . ? C4 C3 N1 C14 7.1(6) . . . . ? C2 C3 N1 C16 19.3(6) . . . . ? C4 C3 N1 C16 -161.2(4) . . . . ? C2 C3 N1 C16* -27.6(7) . . . . ? C4 C3 N1 C16* 152.0(5) . . . . ? C15 C14 N1 C3 -86.2(6) . . . . ? C15 C14 N1 C16 82.6(5) . . . . ? C15 C14 N1 C16* 127.7(6) . . . . ? C17 C16 N1 C3 -100.3(6) . . . . ? C17 C16 N1 C14 90.8(6) . . . . ? C17 C16 N1 C16* -3.9(10) . . . . ? C17* C16* N1 C3 96.1(10) . . . . ? C17* C16* N1 C14 -115.8(9) . . . . ? C17* C16* N1 C16 -11.0(8) . . . . ? C10 C11 N2 C18 -5.8(6) . . . . ? C12 C11 N2 C18 173.9(4) . . . . ? C10 C11 N2 C20 167.4(4) . . . . ? C12 C11 N2 C20 -13.0(6) . . . . ? C10 C11 N2 C20* -137.3(8) . . . . ? C12 C11 N2 C20* 42.3(9) . . . . ? C19 C18 N2 C11 -74.5(6) . . . . ? C19 C18 N2 C20 112.1(5) . . . . ? C19 C18 N2 C20* 62.4(9) . . . . ? C21 C20 N2 C11 88.3(5) . . . . ? C21 C20 N2 C18 -98.3(5) . . . . ? C21 C20 N2 C20* -13.3(11) . . . . ? C21* C20* N2 C11 -108.2(16) . . . . ? C21* C20* N2 C18 113.4(16) . . . . ? C21* C20* N2 C20 -0.8(13) . . . . ? O2 C28 N3 N4 -8.0(7) . . . . ? C27 C28 N3 N4 171.9(3) . . . . ? O2 C28 N3 C7 -173.5(4) . . . . ? C27 C28 N3 C7 6.4(4) . . . . ? C6 C7 N3 C28 109.0(4) . . . . ? C8 C7 N3 C28 -127.2(4) . . . . ? C22 C7 N3 C28 -8.3(4) . . . . ? C6 C7 N3 N4 -59.2(4) . . . . ? C8 C7 N3 N4 64.7(4) . . . . ? C22 C7 N3 N4 -176.4(3) . . . . ? C30 C29 N4 N3 -177.4(3) . . . . ? C28 N3 N4 C29 18.1(6) . . . . ? C7 N3 N4 C29 -176.0(3) . . . . ? C2 C1 O1 C13 172.1(3) . . . . ? C6 C1 O1 C13 -8.1(5) . . . . ? C8 C13 O1 C1 10.5(5) . . . . ? C12 C13 O1 C1 -170.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.307 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.056