# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Debasish Haldar' _publ_contact_author_address ; BCKV campus main office Mohonpur, Haringhata Nadia Kolkata West Bengal India 745212 ; _publ_contact_author_email 'deba h76@yahoo.com' loop_ _publ_author_name P.Jana S.Maity 'Debasish Haldar' data_dh2_0m _database_code_depnum_ccdc_archive 'CCDC 753226' #TrackingRef '- Tyr-Aib-Val.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Tyr-Aib-Val ; _chemical_name_common Tyr-Aib-Val _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H37 N3 O7' _chemical_formula_weight 479.57 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.840(10) _cell_length_b 14.535(13) _cell_length_c 18.079(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2848(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6166 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 26.1 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.118 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.521101 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.3196 before correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 21738 _diffrn_reflns_av_R_equivalents 0.1213 _diffrn_reflns_av_sigmaI/netI 0.1903 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5000 _reflns_number_gt 3144 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0000P)^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 0.3(10) _refine_ls_number_reflns 5000 _refine_ls_number_parameters 359 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1266 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.0919 _refine_ls_wR_factor_gt 0.0828 _refine_ls_goodness_of_fit_ref 0.920 _refine_ls_restrained_S_all 0.920 _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 N2 N 0.56371(18) 0.59448(16) -0.00467(10) 0.0448(5) Uani 1 1 d . . . O5 O 0.83238(17) 0.46567(13) 0.21008(9) 0.0653(5) Uani 1 1 d . . . N1 N 0.7917(2) 0.61485(16) 0.21439(11) 0.0520(6) Uani 1 1 d . . . O7 O 0.39973(14) 0.67585(14) -0.04581(9) 0.0594(5) Uani 1 1 d . . . O6 O 0.54736(13) 0.67170(12) 0.16050(8) 0.0539(4) Uani 1 1 d . . . N3 N 0.65893(16) 0.74458(14) 0.07138(9) 0.0380(4) Uani 1 1 d . . . O4 O 0.78926(17) 0.54416(14) 0.10257(8) 0.0645(5) Uani 1 1 d . . . O3 O 0.73181(17) 0.47238(16) -0.05076(10) 0.0779(6) Uani 1 1 d . . . C9 C 0.76237(19) 0.70657(16) 0.18706(11) 0.0409(6) Uani 1 1 d . . . O2 O 0.5689(2) 1.13672(16) 0.20923(12) 0.0873(8) Uani 1 1 d . . . C11 C 0.49938(19) 0.67295(18) -0.01148(10) 0.0405(5) Uani 1 1 d . . . C12 C 0.8039(2) 0.54151(19) 0.16936(12) 0.0504(6) Uani 1 1 d . . . C13 C 0.7368(2) 0.76944(19) 0.25503(11) 0.0478(6) Uani 1 1 d . . . O1 O 0.59891(19) 0.41031(16) -0.13167(9) 0.0879(7) Uani 1 1 d . . . C15 C 0.64604(18) 0.70502(15) 0.13819(10) 0.0369(5) Uani 1 1 d . . . C16 C 0.6912(2) 0.86522(17) 0.23786(10) 0.0445(6) Uani 1 1 d . . . C17 C 0.8677(3) 0.3775(2) 0.17501(15) 0.0667(8) Uani 1 1 d . . . C18 C 0.6195(3) 0.4575(2) -0.07833(12) 0.0560(7) Uani 1 1 d . . . C19 C 0.4679(2) 0.4441(2) 0.03038(13) 0.0562(7) Uani 1 1 d . . . C20 C 0.5193(2) 0.50585(17) -0.03322(11) 0.0465(6) Uani 1 1 d . . . C21 C 0.6059(3) 1.0463(2) 0.21786(12) 0.0593(7) Uani 1 1 d . . . C22 C 0.7632(3) 0.9309(2) 0.20279(14) 0.0634(8) Uani 1 1 d . . . C23 C 0.3493(3) 0.4873(2) 0.06120(16) 0.0799(10) Uani 1 1 d . . . H23A H 0.3176 0.4495 0.1004 0.120 Uiso 1 1 calc R . . H23B H 0.2890 0.4918 0.0225 0.120 Uiso 1 1 calc R . . H23C H 0.3671 0.5476 0.0800 0.120 Uiso 1 1 calc R . . C24 C 0.55485(19) 0.76254(17) 0.01916(11) 0.0442(6) Uani 1 1 d . . . C25 C 0.7222(3) 1.0203(2) 0.19244(16) 0.0718(9) Uani 1 1 d . . . C26 C 0.4547(2) 0.8210(2) 0.05605(15) 0.0723(8) Uani 1 1 d . . . H26A H 0.4217 0.7885 0.0978 0.108 Uiso 1 1 calc R . . H26B H 0.3900 0.8331 0.0212 0.108 Uiso 1 1 calc R . . H26C H 0.4898 0.8782 0.0724 0.108 Uiso 1 1 calc R . . C27 C 0.8898(3) 0.3159(3) 0.2427(2) 0.0970(11) Uani 1 1 d . . . H27A H 0.9571 0.3401 0.2712 0.145 Uiso 1 1 calc R . . H27B H 0.9095 0.2547 0.2266 0.145 Uiso 1 1 calc R . . H27C H 0.8167 0.3143 0.2726 0.145 Uiso 1 1 calc R . . C28 C 0.5733(2) 0.8922(2) 0.25961(14) 0.0575(7) Uani 1 1 d . . . C29 C 0.6102(3) 0.8136(2) -0.04816(14) 0.0754(9) Uani 1 1 d . . . H29A H 0.6463 0.8705 -0.0321 0.113 Uiso 1 1 calc R . . H29B H 0.5462 0.8261 -0.0835 0.113 Uiso 1 1 calc R . . H29C H 0.6725 0.7760 -0.0707 0.113 Uiso 1 1 calc R . . C30 C 0.7616(3) 0.3399(2) 0.1279(2) 0.0874(10) Uani 1 1 d . . . H30A H 0.7501 0.3787 0.0854 0.131 Uiso 1 1 calc R . . H30B H 0.6873 0.3390 0.1567 0.131 Uiso 1 1 calc R . . H30C H 0.7810 0.2786 0.1119 0.131 Uiso 1 1 calc R . . C31 C 0.5311(3) 0.9816(2) 0.25052(15) 0.0657(8) Uani 1 1 d . . . C32 C 0.4459(4) 0.3451(2) 0.00650(19) 0.1084(13) Uani 1 1 d . . . H32A H 0.4146 0.3104 0.0476 0.163 Uiso 1 1 calc R . . H32B H 0.5222 0.3186 -0.0100 0.163 Uiso 1 1 calc R . . H32C H 0.3871 0.3440 -0.0332 0.163 Uiso 1 1 calc R . . C33 C 0.9855(3) 0.3914(2) 0.13096(19) 0.0919(10) Uani 1 1 d . . . H33A H 0.9685 0.4290 0.0885 0.138 Uiso 1 1 calc R . . H33B H 1.0166 0.3327 0.1151 0.138 Uiso 1 1 calc R . . H33C H 1.0460 0.4212 0.1615 0.138 Uiso 1 1 calc R . . C34 C 0.8358(3) 0.4277(3) -0.08762(18) 0.0972(12) Uani 1 1 d . . . H34A H 0.9111 0.4441 -0.0629 0.146 Uiso 1 1 calc R . . H34B H 0.8395 0.4475 -0.1382 0.146 Uiso 1 1 calc R . . H34C H 0.8252 0.3622 -0.0859 0.146 Uiso 1 1 calc R . . H9 H 0.8283(17) 0.7366(14) 0.1569(10) 0.029(5) Uiso 1 1 d . . . H333 H 0.735(2) 0.7645(16) 0.0597(11) 0.042(6) Uiso 1 1 d . . . H31 H 0.451(3) 1.000(2) 0.2598(16) 0.096(10) Uiso 1 1 d . . . H13B H 0.817(2) 0.7677(17) 0.2825(13) 0.063(7) Uiso 1 1 d . . . H13A H 0.666(2) 0.7358(17) 0.2843(12) 0.059(7) Uiso 1 1 d . . . H22 H 0.836(2) 0.9150(19) 0.1829(13) 0.067(8) Uiso 1 1 d . . . H20 H 0.451(2) 0.5188(17) -0.0658(11) 0.052(6) Uiso 1 1 d . . . H222 H 0.623(2) 0.5940(19) 0.0194(13) 0.057(8) Uiso 1 1 d . . . H28 H 0.526(3) 0.846(2) 0.2887(15) 0.087(9) Uiso 1 1 d . . . H19 H 0.527(2) 0.4518(17) 0.0714(11) 0.055(6) Uiso 1 1 d . . . H111 H 0.810(2) 0.6108(18) 0.2555(14) 0.056(8) Uiso 1 1 d . . . H25 H 0.771(3) 1.066(3) 0.1699(17) 0.100(11) Uiso 1 1 d . . . H2 H 0.532(3) 1.151(2) 0.2420(15) 0.074(10) 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 N2 0.0416(10) 0.0454(16) 0.0476(10) -0.0062(9) -0.0121(9) 0.0039(11) O5 0.0892(13) 0.0424(12) 0.0644(9) 0.0070(9) -0.0040(9) 0.0163(10) N1 0.0720(13) 0.0434(15) 0.0405(9) 0.0034(10) -0.0059(9) 0.0137(11) O7 0.0487(9) 0.0585(13) 0.0710(10) -0.0063(9) -0.0219(8) 0.0045(9) O6 0.0469(9) 0.0579(12) 0.0569(9) 0.0018(8) 0.0051(7) -0.0136(9) N3 0.0320(9) 0.0374(13) 0.0447(9) 0.0037(8) -0.0034(7) -0.0019(9) O4 0.0865(12) 0.0572(14) 0.0500(8) -0.0039(9) -0.0093(8) 0.0190(10) O3 0.0680(12) 0.0924(18) 0.0733(11) -0.0370(11) 0.0004(9) 0.0202(12) C9 0.0421(12) 0.0399(17) 0.0408(10) 0.0035(10) -0.0004(9) -0.0002(11) O2 0.1212(18) 0.0604(17) 0.0803(13) 0.0109(11) 0.0386(13) 0.0337(14) C11 0.0361(10) 0.0438(17) 0.0418(10) 0.0012(10) -0.0022(9) 0.0039(12) C12 0.0538(14) 0.0440(18) 0.0532(13) 0.0044(13) -0.0004(10) 0.0086(13) C13 0.0589(15) 0.0452(18) 0.0393(10) -0.0026(10) -0.0012(11) 0.0014(13) O1 0.0979(14) 0.1045(19) 0.0613(10) -0.0423(12) 0.0066(10) -0.0007(14) C15 0.0402(11) 0.0290(15) 0.0416(10) -0.0037(10) 0.0038(8) -0.0024(10) C16 0.0535(13) 0.0418(16) 0.0383(10) -0.0069(10) 0.0005(10) 0.0019(13) C17 0.0645(17) 0.0418(19) 0.0940(19) -0.0019(16) -0.0076(14) 0.0184(14) C18 0.0719(17) 0.0526(19) 0.0435(11) -0.0041(13) 0.0034(11) 0.0071(15) C19 0.0631(16) 0.0487(19) 0.0569(13) -0.0028(12) -0.0050(12) -0.0013(14) C20 0.0519(13) 0.0417(17) 0.0458(11) -0.0072(10) -0.0113(10) 0.0026(12) C21 0.0825(18) 0.043(2) 0.0522(12) -0.0011(13) 0.0155(13) 0.0178(16) C22 0.0628(17) 0.056(2) 0.0718(16) 0.0074(14) 0.0294(14) 0.0139(16) C23 0.0619(17) 0.095(3) 0.0830(18) 0.0141(17) 0.0102(14) 0.0016(18) C24 0.0404(11) 0.0394(16) 0.0529(11) 0.0085(11) -0.0126(10) 0.0042(12) C25 0.086(2) 0.048(2) 0.0818(17) 0.0130(15) 0.0341(16) 0.0093(18) C26 0.0619(16) 0.055(2) 0.1002(19) -0.0233(16) -0.0280(14) 0.0262(16) C27 0.097(2) 0.061(2) 0.132(3) 0.032(2) -0.013(2) 0.019(2) C28 0.0587(16) 0.046(2) 0.0675(15) -0.0035(14) 0.0106(12) -0.0026(15) C29 0.0756(17) 0.078(2) 0.0723(15) 0.0344(15) -0.0282(14) -0.0197(18) C30 0.083(2) 0.056(3) 0.123(3) -0.019(2) -0.0157(18) 0.0053(19) C31 0.0591(17) 0.063(2) 0.0753(16) -0.0023(14) 0.0160(14) 0.0129(17) C32 0.155(4) 0.058(3) 0.112(3) -0.009(2) 0.026(3) -0.029(3) C33 0.0699(19) 0.084(3) 0.122(3) -0.001(2) 0.0028(18) 0.0203(19) C34 0.078(2) 0.113(3) 0.101(2) -0.036(2) 0.0141(17) 0.024(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N2 C11 1.342(3) . ? N2 C20 1.469(3) . ? N2 H222 0.77(3) . ? O5 C12 1.361(3) . ? O5 C17 1.481(3) . ? N1 C12 1.348(3) . ? N1 C9 1.457(3) . ? N1 H111 0.77(2) . ? O7 C11 1.246(3) . ? O6 C15 1.241(2) . ? N3 C15 1.345(3) . ? N3 C24 1.494(3) . ? N3 H333 0.90(2) . ? O4 C12 1.219(3) . ? O3 C18 1.334(3) . ? O3 C34 1.462(3) . ? C9 C15 1.540(3) . ? C9 C13 1.556(3) . ? C9 H9 0.999(19) . ? O2 C21 1.383(3) . ? O2 H2 0.74(3) . ? C11 C24 1.537(4) . ? C13 C16 1.510(4) . ? C13 H13B 1.01(3) . ? C13 H13A 1.05(2) . ? O1 C18 1.204(3) . ? C16 C22 1.387(4) . ? C16 C28 1.393(4) . ? C17 C33 1.519(4) . ? C17 C30 1.531(4) . ? C17 C27 1.535(4) . ? C18 C20 1.529(3) . ? C19 C32 1.521(5) . ? C19 C23 1.536(4) . ? C19 C20 1.561(4) . ? C19 H19 0.99(2) . ? C20 H20 0.97(2) . ? C21 C31 1.376(4) . ? C21 C25 1.394(4) . ? C22 C25 1.385(4) . ? C22 H22 0.90(3) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C26 1.531(3) . ? C24 C29 1.547(3) . ? C25 H25 0.94(3) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 C31 1.387(4) . ? C28 H28 0.99(3) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31 0.92(3) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? 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 C11 N2 C20 122.9(2) . . ? C11 N2 H222 119(2) . . ? C20 N2 H222 117(2) . . ? C12 O5 C17 121.89(19) . . ? C12 N1 C9 122.7(2) . . ? C12 N1 H111 120(2) . . ? C9 N1 H111 117(2) . . ? C15 N3 C24 124.31(18) . . ? C15 N3 H333 116.4(13) . . ? C24 N3 H333 119.2(13) . . ? C18 O3 C34 117.5(2) . . ? N1 C9 C15 111.08(19) . . ? N1 C9 C13 107.95(18) . . ? C15 C9 C13 108.43(18) . . ? N1 C9 H9 115.4(11) . . ? C15 C9 H9 106.2(10) . . ? C13 C9 H9 107.6(11) . . ? C21 O2 H2 110(2) . . ? O7 C11 N2 121.6(2) . . ? O7 C11 C24 119.3(2) . . ? N2 C11 C24 118.90(18) . . ? O4 C12 N1 124.1(3) . . ? O4 C12 O5 126.2(3) . . ? N1 C12 O5 109.6(2) . . ? C16 C13 C9 115.93(18) . . ? C16 C13 H13B 114.2(15) . . ? C9 C13 H13B 102.8(14) . . ? C16 C13 H13A 107.1(13) . . ? C9 C13 H13A 104.7(13) . . ? H13B C13 H13A 112.0(18) . . ? O6 C15 N3 123.23(18) . . ? O6 C15 C9 121.66(18) . . ? N3 C15 C9 115.08(18) . . ? C22 C16 C28 116.8(3) . . ? C22 C16 C13 123.0(2) . . ? C28 C16 C13 120.2(2) . . ? O5 C17 C33 109.1(2) . . ? O5 C17 C30 110.7(2) . . ? C33 C17 C30 112.8(3) . . ? O5 C17 C27 101.8(2) . . ? C33 C17 C27 111.3(3) . . ? C30 C17 C27 110.7(3) . . ? O1 C18 O3 124.1(2) . . ? O1 C18 C20 123.9(2) . . ? O3 C18 C20 112.0(2) . . ? C32 C19 C23 111.0(3) . . ? C32 C19 C20 113.0(2) . . ? C23 C19 C20 109.3(2) . . ? C32 C19 H19 115.0(15) . . ? C23 C19 H19 103.0(13) . . ? C20 C19 H19 105.0(13) . . ? N2 C20 C18 111.0(2) . . ? N2 C20 C19 111.24(19) . . ? C18 C20 C19 112.5(2) . . ? N2 C20 H20 107.1(15) . . ? C18 C20 H20 108.1(13) . . ? C19 C20 H20 106.6(13) . . ? C31 C21 O2 121.8(3) . . ? C31 C21 C25 119.3(3) . . ? O2 C21 C25 118.9(3) . . ? C25 C22 C16 121.7(3) . . ? C25 C22 H22 118.0(18) . . ? C16 C22 H22 120.1(18) . . ? C19 C23 H23A 109.5 . . ? C19 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C19 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N3 C24 C26 110.90(18) . . ? N3 C24 C11 112.03(19) . . ? C26 C24 C11 110.5(2) . . ? N3 C24 C29 106.75(19) . . ? C26 C24 C29 110.6(2) . . ? C11 C24 C29 105.95(19) . . ? C22 C25 C21 120.1(3) . . ? C22 C25 H25 123(2) . . ? C21 C25 H25 117(2) . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C17 C27 H27A 109.5 . . ? C17 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C17 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C31 C28 C16 122.2(3) . . ? C31 C28 H28 121.8(17) . . ? C16 C28 H28 115.3(17) . . ? C24 C29 H29A 109.5 . . ? C24 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C24 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C17 C30 H30A 109.5 . . ? C17 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C17 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C21 C31 C28 119.8(3) . . ? C21 C31 H31 116(2) . . ? C28 C31 H31 124(2) . . ? C19 C32 H32A 109.5 . . ? C19 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C19 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C17 C33 H33A 109.5 . . ? C17 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C17 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? O3 C34 H34A 109.5 . . ? O3 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? O3 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 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 C12 N1 C9 C15 53.1(3) . . . . ? C12 N1 C9 C13 171.8(2) . . . . ? C20 N2 C11 O7 -3.4(3) . . . . ? C20 N2 C11 C24 -179.00(18) . . . . ? C9 N1 C12 O4 -1.7(4) . . . . ? C9 N1 C12 O5 179.4(2) . . . . ? C17 O5 C12 O4 9.4(4) . . . . ? C17 O5 C12 N1 -171.8(2) . . . . ? N1 C9 C13 C16 -173.6(2) . . . . ? C15 C9 C13 C16 -53.2(3) . . . . ? C24 N3 C15 O6 6.8(3) . . . . ? C24 N3 C15 C9 -171.3(2) . . . . ? N1 C9 C15 O6 53.9(3) . . . . ? C13 C9 C15 O6 -64.6(3) . . . . ? N1 C9 C15 N3 -128.0(2) . . . . ? C13 C9 C15 N3 113.5(2) . . . . ? C9 C13 C16 C22 -67.0(3) . . . . ? C9 C13 C16 C28 115.3(2) . . . . ? C12 O5 C17 C33 62.3(3) . . . . ? C12 O5 C17 C30 -62.3(3) . . . . ? C12 O5 C17 C27 -180.0(2) . . . . ? C34 O3 C18 O1 -0.5(4) . . . . ? C34 O3 C18 C20 178.3(3) . . . . ? C11 N2 C20 C18 131.2(2) . . . . ? C11 N2 C20 C19 -102.8(2) . . . . ? O1 C18 C20 N2 -145.9(3) . . . . ? O3 C18 C20 N2 35.3(3) . . . . ? O1 C18 C20 C19 88.8(3) . . . . ? O3 C18 C20 C19 -90.0(3) . . . . ? C32 C19 C20 N2 -168.0(3) . . . . ? C23 C19 C20 N2 67.9(3) . . . . ? C32 C19 C20 C18 -42.8(3) . . . . ? C23 C19 C20 C18 -167.0(2) . . . . ? C28 C16 C22 C25 2.5(4) . . . . ? C13 C16 C22 C25 -175.3(3) . . . . ? C15 N3 C24 C26 56.3(3) . . . . ? C15 N3 C24 C11 -67.7(3) . . . . ? C15 N3 C24 C29 176.7(2) . . . . ? O7 C11 C24 N3 168.22(18) . . . . ? N2 C11 C24 N3 -16.1(3) . . . . ? O7 C11 C24 C26 44.0(3) . . . . ? N2 C11 C24 C26 -140.3(2) . . . . ? O7 C11 C24 C29 -75.8(2) . . . . ? N2 C11 C24 C29 100.0(2) . . . . ? C16 C22 C25 C21 0.3(5) . . . . ? C31 C21 C25 C22 -2.6(4) . . . . ? O2 C21 C25 C22 177.7(3) . . . . ? C22 C16 C28 C31 -3.3(4) . . . . ? C13 C16 C28 C31 174.6(2) . . . . ? O2 C21 C31 C28 -178.4(2) . . . . ? C25 C21 C31 C28 1.8(4) . . . . ? C16 C28 C31 C21 1.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.943 _refine_diff_density_max 0.111 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.034