# Electronic Supplementary Material (ESI) for Soft Matter # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Soft Matter' _journal_coden_cambridge 0777 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Pathik Sahoo' _publ_contact_author_email 2c.pathik@gmail.com _publ_author_name 'Parthasarathi Dastidar' data_aj50_0m _database_code_depnum_ccdc_archive 'CCDC 819160' #TrackingRef '1.15- F.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_absolute_configuration syn _chemical_melting_point ? _chemical_formula_moiety 'C15 H34 N, C14 H9 N2 O4' _chemical_formula_sum 'C29 H43 N3 O4' _chemical_formula_weight 497.66 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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.4221(11) _cell_length_b 14.631(3) _cell_length_c 15.001(3) _cell_angle_alpha 95.239(6) _cell_angle_beta 94.880(7) _cell_angle_gamma 99.656(7) _cell_volume 1376.5(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PLATE _exptl_crystal_colour ORANGE _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.201 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 540 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9673 _exptl_absorpt_correction_T_max 0.9889 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10569 _diffrn_reflns_av_R_equivalents 0.1166 _diffrn_reflns_av_sigmaI/netI 0.1018 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 20.76 _reflns_number_total 2854 _reflns_number_gt 1429 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER APEX II' _computing_cell_refinement 'BRUKER APEX II' _computing_data_reduction 'BRUKER APEX II' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97, PLATON, MERCURY 2.2' _computing_publication_material 'SHELXL-97, PLATON, MERCURY 2.2' _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^)+(0.0794P)^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 2854 _refine_ls_number_parameters 331 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1428 _refine_ls_R_factor_gt 0.0634 _refine_ls_wR_factor_ref 0.1769 _refine_ls_wR_factor_gt 0.1386 _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_restrained_S_all 0.957 _refine_ls_shift/su_max 0.006 _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 0.4359(6) 0.8904(3) 0.0371(3) 0.0399(11) Uani 1 1 d . . . O2 O 0.1760(6) 0.9479(3) 0.0989(2) 0.0333(10) Uani 1 1 d . . . C3 C 0.3436(10) 0.9174(4) 0.1039(4) 0.0315(16) Uani 1 1 d . . . C4 C 0.4526(9) 0.9085(4) 0.1962(3) 0.0265(15) Uani 1 1 d . . . C5 C 0.3599(9) 0.9328(4) 0.2721(4) 0.0295(15) Uani 1 1 d . . . H5 H 0.2272 0.9534 0.2663 0.035 Uiso 1 1 calc R . . C6 C 0.4575(9) 0.9275(4) 0.3570(4) 0.0328(15) Uani 1 1 d . . . H6 H 0.3932 0.9454 0.4090 0.039 Uiso 1 1 calc R . . C7 C 0.6489(9) 0.8963(4) 0.3656(4) 0.0266(15) Uani 1 1 d . . . C8 C 0.7417(9) 0.8709(4) 0.2905(4) 0.0368(17) Uani 1 1 d . . . H8 H 0.8727 0.8489 0.2962 0.044 Uiso 1 1 calc R . . C9 C 0.6439(9) 0.8774(4) 0.2071(4) 0.0412(17) Uani 1 1 d . . . H9 H 0.7095 0.8600 0.1552 0.049 Uiso 1 1 calc R . . N10 N 0.7365(7) 0.8947(3) 0.4571(3) 0.0302(13) Uani 1 1 d . . . N11 N 0.9127(8) 0.8678(3) 0.4627(3) 0.0315(13) Uani 1 1 d . . . C13 C 1.0009(9) 0.8664(4) 0.5541(3) 0.0244(14) Uani 1 1 d . . . C14 C 0.9075(8) 0.8953(4) 0.6287(4) 0.0294(15) Uani 1 1 d . . . H14 H 0.7739 0.9149 0.6219 0.035 Uiso 1 1 calc R . . C15 C 1.0113(9) 0.8955(4) 0.7141(4) 0.0329(16) Uani 1 1 d . . . H15 H 0.9474 0.9144 0.7659 0.040 Uiso 1 1 calc R . . C16 C 1.2082(9) 0.8681(4) 0.7235(4) 0.0260(15) Uani 1 1 d . . . C17 C 1.2975(8) 0.8373(4) 0.6484(4) 0.0305(15) Uani 1 1 d . . . H17 H 1.4300 0.8166 0.6549 0.037 Uiso 1 1 calc R . . C18 C 1.1931(9) 0.8368(4) 0.5634(4) 0.0366(16) Uani 1 1 d . . . H18 H 1.2545 0.8159 0.5115 0.044 Uiso 1 1 calc R . . C19 C 1.3281(10) 0.8714(4) 0.8149(4) 0.0302(15) Uani 1 1 d . . . O20 O 1.5044(7) 0.8518(3) 0.8231(2) 0.0428(12) Uani 1 1 d . . . O21 O 1.2267(6) 0.8990(3) 0.8826(3) 0.0409(12) Uani 1 1 d . . . N22 N 1.1737(6) 0.1287(3) 1.0256(3) 0.0327(13) Uani 1 1 d . . . H22A H 1.0490 0.1118 0.9897 0.049 Uiso 1 1 calc R . . H22B H 1.1712 0.0944 1.0732 0.049 Uiso 1 1 calc R . . H22C H 1.2831 0.1184 0.9935 0.049 Uiso 1 1 calc R . . C23 C 1.2031(9) 0.2299(4) 1.0590(4) 0.0450(18) Uani 1 1 d . . . H23A H 1.3481 0.2602 1.0494 0.054 Uiso 1 1 calc R . . H23B H 1.1913 0.2359 1.1245 0.054 Uiso 1 1 calc R . . C24 C 1.0436(9) 0.2810(4) 1.0133(4) 0.0434(17) Uani 1 1 d . . . H24A H 1.0659 0.3456 1.0432 0.052 Uiso 1 1 calc R . . H24B H 0.8991 0.2504 1.0231 0.052 Uiso 1 1 calc R . . C25 C 1.0525(9) 0.2856(4) 0.9125(3) 0.0373(16) Uani 1 1 d . . . H25A H 1.1919 0.3214 0.9022 0.045 Uiso 1 1 calc R . . H25B H 1.0404 0.2217 0.8822 0.045 Uiso 1 1 calc R . . C26 C 0.8767(9) 0.3311(4) 0.8706(3) 0.0395(17) Uani 1 1 d . . . H26A H 0.7392 0.2999 0.8878 0.047 Uiso 1 1 calc R . . H26B H 0.8992 0.3971 0.8966 0.047 Uiso 1 1 calc R . . C27 C 0.8619(9) 0.3283(4) 0.7709(4) 0.0387(16) Uani 1 1 d . . . H27A H 0.8587 0.2633 0.7448 0.046 Uiso 1 1 calc R . . H27B H 0.9910 0.3671 0.7538 0.046 Uiso 1 1 calc R . . C28 C 0.6671(9) 0.3625(4) 0.7299(3) 0.0377(16) Uani 1 1 d . . . H28A H 0.5398 0.3290 0.7535 0.045 Uiso 1 1 calc R . . H28B H 0.6797 0.4296 0.7507 0.045 Uiso 1 1 calc R . . C29 C 0.6319(9) 0.3502(4) 0.6280(3) 0.0407(17) Uani 1 1 d . . . H29A H 0.7513 0.3891 0.6040 0.049 Uiso 1 1 calc R . . H29B H 0.6326 0.2843 0.6064 0.049 Uiso 1 1 calc R . . C30 C 0.4260(9) 0.3764(4) 0.5913(4) 0.0404(17) Uani 1 1 d . . . H30A H 0.3074 0.3381 0.6164 0.048 Uiso 1 1 calc R . . H30B H 0.4266 0.4425 0.6129 0.048 Uiso 1 1 calc R . . C31 C 0.3838(9) 0.3642(4) 0.4899(3) 0.0378(16) Uani 1 1 d . . . H31A H 0.3791 0.2978 0.4681 0.045 Uiso 1 1 calc R . . H31B H 0.5032 0.4015 0.4645 0.045 Uiso 1 1 calc R . . C32 C 0.1787(9) 0.3930(4) 0.4556(4) 0.0398(17) Uani 1 1 d . . . H32A H 0.1844 0.4593 0.4778 0.048 Uiso 1 1 calc R . . H32B H 0.0603 0.3559 0.4819 0.048 Uiso 1 1 calc R . . C33 C 0.1287(9) 0.3817(4) 0.3542(3) 0.0370(16) Uani 1 1 d . . . H33A H 0.1218 0.3154 0.3315 0.044 Uiso 1 1 calc R . . H33B H 0.2462 0.4190 0.3275 0.044 Uiso 1 1 calc R . . C34 C -0.0790(9) 0.4116(4) 0.3223(3) 0.0413(17) Uani 1 1 d . . . H34A H -0.1967 0.3725 0.3472 0.050 Uiso 1 1 calc R . . H34B H -0.0742 0.4770 0.3474 0.050 Uiso 1 1 calc R . . C35 C -0.1278(9) 0.4048(4) 0.2219(4) 0.0424(17) Uani 1 1 d . . . H35A H -0.1328 0.3395 0.1963 0.051 Uiso 1 1 calc R . . H35B H -0.0114 0.4444 0.1967 0.051 Uiso 1 1 calc R . . C36 C -0.3355(10) 0.4345(4) 0.1932(4) 0.0534(19) Uani 1 1 d . . . H36A H -0.3395 0.4956 0.2266 0.064 Uiso 1 1 calc R . . H36B H -0.4534 0.3888 0.2102 0.064 Uiso 1 1 calc R . . C37 C -0.3721(10) 0.4425(5) 0.0921(4) 0.064(2) Uani 1 1 d D . . H37A H -0.2696 0.4945 0.0763 0.096 Uiso 1 1 calc RD . . H37B H -0.5166 0.4537 0.0773 0.096 Uiso 1 1 calc R . . H37C H -0.3535 0.3844 0.0582 0.096 Uiso 1 1 calc R . . H21 H 1.306(10) 0.894(4) 0.939(5) 0.08(2) 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 O1 0.035(3) 0.066(3) 0.021(3) 0.009(2) -0.004(2) 0.017(2) O2 0.033(3) 0.043(3) 0.025(2) 0.0054(18) -0.008(2) 0.015(2) C3 0.026(4) 0.041(4) 0.026(4) 0.003(3) 0.000(3) 0.003(3) C4 0.032(4) 0.031(4) 0.016(4) 0.002(3) -0.007(3) 0.006(3) C5 0.029(4) 0.042(4) 0.019(4) 0.003(3) -0.004(3) 0.016(3) C6 0.030(4) 0.049(4) 0.021(4) 0.002(3) 0.003(3) 0.011(3) C7 0.032(4) 0.033(4) 0.015(4) 0.006(3) -0.003(3) 0.008(3) C8 0.035(4) 0.066(5) 0.014(4) 0.007(3) 0.001(3) 0.024(4) C9 0.040(4) 0.070(5) 0.019(4) 0.004(3) 0.000(3) 0.027(4) N10 0.032(3) 0.045(3) 0.015(3) 0.006(2) -0.008(2) 0.013(3) N11 0.032(3) 0.038(3) 0.025(3) 0.007(2) -0.007(3) 0.008(3) C13 0.029(4) 0.033(4) 0.011(4) 0.008(3) -0.004(3) 0.006(3) C14 0.022(4) 0.044(4) 0.023(4) 0.002(3) -0.007(3) 0.014(3) C15 0.029(4) 0.053(4) 0.021(4) 0.005(3) 0.006(3) 0.015(3) C16 0.026(4) 0.030(4) 0.021(4) 0.006(3) -0.003(3) 0.005(3) C17 0.024(3) 0.043(4) 0.027(4) 0.006(3) -0.003(3) 0.013(3) C18 0.038(4) 0.049(4) 0.025(4) 0.006(3) -0.002(3) 0.016(4) C19 0.035(4) 0.026(4) 0.027(4) 0.007(3) -0.012(4) 0.004(3) O20 0.039(3) 0.068(3) 0.024(2) 0.004(2) -0.009(2) 0.021(3) O21 0.043(3) 0.071(3) 0.011(2) 0.007(2) -0.006(2) 0.019(2) N22 0.029(3) 0.047(3) 0.024(3) 0.012(2) -0.005(2) 0.010(3) C23 0.052(4) 0.042(4) 0.037(4) 0.000(3) -0.018(3) 0.011(4) C24 0.046(4) 0.046(4) 0.042(4) 0.010(3) -0.001(3) 0.018(4) C25 0.039(4) 0.043(4) 0.036(4) 0.021(3) 0.002(3) 0.016(3) C26 0.048(4) 0.041(4) 0.033(4) 0.009(3) -0.004(3) 0.017(3) C27 0.050(4) 0.036(4) 0.031(4) 0.010(3) -0.003(3) 0.014(3) C28 0.050(4) 0.035(4) 0.031(4) 0.006(3) 0.003(3) 0.013(3) C29 0.046(4) 0.043(4) 0.033(4) 0.010(3) -0.003(3) 0.010(3) C30 0.039(4) 0.046(4) 0.035(4) 0.005(3) -0.002(3) 0.007(3) C31 0.047(4) 0.035(4) 0.030(4) 0.008(3) -0.001(3) 0.004(3) C32 0.043(4) 0.047(4) 0.031(4) 0.010(3) 0.000(3) 0.013(3) C33 0.049(4) 0.033(4) 0.029(4) 0.006(3) -0.004(3) 0.012(3) C34 0.053(4) 0.040(4) 0.030(4) 0.007(3) 0.000(3) 0.010(3) C35 0.048(4) 0.043(4) 0.033(4) 0.005(3) -0.008(3) 0.006(4) C36 0.056(5) 0.068(5) 0.035(4) 0.002(3) -0.013(3) 0.018(4) C37 0.067(5) 0.078(5) 0.045(4) 0.016(4) -0.019(4) 0.014(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 C3 1.272(6) . ? O2 C3 1.232(6) . ? C3 C4 1.524(7) . ? C4 C5 1.375(7) . ? C4 C9 1.382(7) . ? C5 C6 1.385(7) . ? C5 H5 0.9500 . ? C6 C7 1.382(7) . ? C6 H6 0.9500 . ? C7 C8 1.369(7) . ? C7 N10 1.441(6) . ? C8 C9 1.370(7) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? N10 N11 1.258(5) . ? N11 C13 1.442(6) . ? C13 C18 1.376(7) . ? C13 C14 1.380(7) . ? C14 C15 1.392(7) . ? C14 H14 0.9500 . ? C15 C16 1.390(7) . ? C15 H15 0.9500 . ? C16 C17 1.380(7) . ? C16 C19 1.506(7) . ? C17 C18 1.389(7) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 O20 1.213(6) . ? C19 O21 1.321(7) . ? O21 H21 0.96(7) . ? N22 C23 1.494(6) . ? N22 H22A 0.9100 . ? N22 H22B 0.9100 . ? N22 H22C 0.9100 . ? C23 C24 1.520(7) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.526(7) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.523(7) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.487(7) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.526(7) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.516(7) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.511(7) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 C31 1.511(7) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C32 1.513(7) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C33 1.516(7) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.524(7) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.503(7) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.511(7) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 C37 1.532(8) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 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 O2 C3 O1 125.3(5) . . ? O2 C3 C4 119.2(6) . . ? O1 C3 C4 115.5(5) . . ? C5 C4 C9 118.1(5) . . ? C5 C4 C3 119.4(5) . . ? C9 C4 C3 122.5(6) . . ? C4 C5 C6 120.8(5) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C7 C6 C5 119.7(5) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C8 C7 C6 120.0(5) . . ? C8 C7 N10 125.1(5) . . ? C6 C7 N10 114.8(5) . . ? C7 C8 C9 119.4(5) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C8 C9 C4 121.9(5) . . ? C8 C9 H9 119.0 . . ? C4 C9 H9 119.0 . . ? N11 N10 C7 113.3(4) . . ? N10 N11 C13 113.4(4) . . ? C18 C13 C14 120.7(5) . . ? C18 C13 N11 115.3(5) . . ? C14 C13 N11 123.9(5) . . ? C13 C14 C15 119.3(5) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C16 C15 C14 120.1(5) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C17 C16 C15 120.0(5) . . ? C17 C16 C19 118.8(5) . . ? C15 C16 C19 121.2(6) . . ? C16 C17 C18 119.8(5) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C13 C18 C17 120.1(5) . . ? C13 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? O20 C19 O21 124.3(5) . . ? O20 C19 C16 121.4(6) . . ? O21 C19 C16 114.3(6) . . ? C19 O21 H21 110(4) . . ? C23 N22 H22A 109.5 . . ? C23 N22 H22B 109.5 . . ? H22A N22 H22B 109.5 . . ? C23 N22 H22C 109.5 . . ? H22A N22 H22C 109.5 . . ? H22B N22 H22C 109.5 . . ? N22 C23 C24 113.8(5) . . ? N22 C23 H23A 108.8 . . ? C24 C23 H23A 108.8 . . ? N22 C23 H23B 108.8 . . ? C24 C23 H23B 108.8 . . ? H23A C23 H23B 107.7 . . ? C23 C24 C25 115.9(5) . . ? C23 C24 H24A 108.3 . . ? C25 C24 H24A 108.3 . . ? C23 C24 H24B 108.3 . . ? C25 C24 H24B 108.3 . . ? H24A C24 H24B 107.4 . . ? C26 C25 C24 112.5(5) . . ? C26 C25 H25A 109.1 . . ? C24 C25 H25A 109.1 . . ? C26 C25 H25B 109.1 . . ? C24 C25 H25B 109.1 . . ? H25A C25 H25B 107.8 . . ? C27 C26 C25 115.1(5) . . ? C27 C26 H26A 108.5 . . ? C25 C26 H26A 108.5 . . ? C27 C26 H26B 108.5 . . ? C25 C26 H26B 108.5 . . ? H26A C26 H26B 107.5 . . ? C26 C27 C28 113.9(5) . . ? C26 C27 H27A 108.8 . . ? C28 C27 H27A 108.8 . . ? C26 C27 H27B 108.8 . . ? C28 C27 H27B 108.8 . . ? H27A C27 H27B 107.7 . . ? C29 C28 C27 115.6(5) . . ? C29 C28 H28A 108.4 . . ? C27 C28 H28A 108.4 . . ? C29 C28 H28B 108.4 . . ? C27 C28 H28B 108.4 . . ? H28A C28 H28B 107.4 . . ? C30 C29 C28 113.3(5) . . ? C30 C29 H29A 108.9 . . ? C28 C29 H29A 108.9 . . ? C30 C29 H29B 108.9 . . ? C28 C29 H29B 108.9 . . ? H29A C29 H29B 107.7 . . ? C31 C30 C29 115.0(5) . . ? C31 C30 H30A 108.5 . . ? C29 C30 H30A 108.5 . . ? C31 C30 H30B 108.5 . . ? C29 C30 H30B 108.5 . . ? H30A C30 H30B 107.5 . . ? C30 C31 C32 113.5(5) . . ? C30 C31 H31A 108.9 . . ? C32 C31 H31A 108.9 . . ? C30 C31 H31B 108.9 . . ? C32 C31 H31B 108.9 . . ? H31A C31 H31B 107.7 . . ? C31 C32 C33 115.6(5) . . ? C31 C32 H32A 108.4 . . ? C33 C32 H32A 108.4 . . ? C31 C32 H32B 108.4 . . ? C33 C32 H32B 108.4 . . ? H32A C32 H32B 107.5 . . ? C32 C33 C34 113.9(5) . . ? C32 C33 H33A 108.8 . . ? C34 C33 H33A 108.8 . . ? C32 C33 H33B 108.8 . . ? C34 C33 H33B 108.8 . . ? H33A C33 H33B 107.7 . . ? C35 C34 C33 115.0(5) . . ? C35 C34 H34A 108.5 . . ? C33 C34 H34A 108.5 . . ? C35 C34 H34B 108.5 . . ? C33 C34 H34B 108.5 . . ? H34A C34 H34B 107.5 . . ? C34 C35 C36 113.3(5) . . ? C34 C35 H35A 108.9 . . ? C36 C35 H35A 108.9 . . ? C34 C35 H35B 108.9 . . ? C36 C35 H35B 108.9 . . ? H35A C35 H35B 107.7 . . ? C35 C36 C37 114.1(5) . . ? C35 C36 H36A 108.7 . . ? C37 C36 H36A 108.7 . . ? C35 C36 H36B 108.7 . . ? C37 C36 H36B 108.7 . . ? H36A C36 H36B 107.6 . . ? C36 C37 H37A 109.5 . . ? C36 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C36 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? 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 O21 H21 O1 0.96(7) 1.65(7) 2.602(5) 177(6) 1_656 N22 H22A O2 0.91 1.91 2.801(5) 165.1 2_666 N22 H22C O1 0.91 1.92 2.799(6) 161.5 2_766 N22 H22B O2 0.91 2.22 2.959(5) 138.3 1_646 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 20.76 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.198 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.052 # Attachment '1.16- F.cif' data_adhy_0m _database_code_depnum_ccdc_archive 'CCDC 819161' #TrackingRef '1.16- F.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_absolute_configuration syn _chemical_melting_point ? _chemical_formula_moiety 'c17 H9 N2 O4,C16 H36 N1' _chemical_formula_sum 'C30 H45 N3 O4' _chemical_formula_weight 508.67 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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.323(3) _cell_length_b 14.956(7) _cell_length_c 16.823(8) _cell_angle_alpha 113.730(6) _cell_angle_beta 95.041(7) _cell_angle_gamma 94.696(7) _cell_volume 1438.8(12) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PLATE _exptl_crystal_colour ORANGE _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.174 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 550 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9688 _exptl_absorpt_correction_T_max 0.9923 _exptl_absorpt_process_details SADABS _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 CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7895 _diffrn_reflns_av_R_equivalents 0.0586 _diffrn_reflns_av_sigmaI/netI 0.0676 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 19.37 _reflns_number_total 2443 _reflns_number_gt 1528 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER APEX II' _computing_cell_refinement 'BRUKER APEX II' _computing_data_reduction 'BRUKER APEX II' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97, PLATON, MERCURY 2.2' _computing_publication_material 'SHELXL-97, PLATON, MERCURY 2.2' _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^)+(0.2000P)^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 2443 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1463 _refine_ls_R_factor_gt 0.1073 _refine_ls_wR_factor_ref 0.3499 _refine_ls_wR_factor_gt 0.3101 _refine_ls_goodness_of_fit_ref 1.279 _refine_ls_restrained_S_all 1.279 _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 1.5086(9) 1.2781(3) 0.8519(3) 0.0406(16) Uani 1 1 d . . . O2A O 1.2483(14) 1.3567(6) 0.9164(6) 0.031(3) Uiso 0.57 1 d P . . O2B O 1.2033(16) 1.3427(7) 0.8717(8) 0.017(3) Uiso 0.43 1 d P . . C3 C 1.3290(13) 1.2736(5) 0.8701(4) 0.026(2) Uani 1 1 d . . . C4 C 1.2101(10) 1.1833(5) 0.8673(4) 0.024(2) Uani 1 1 d . . . C5A C 1.038(2) 1.1867(10) 0.9124(11) 0.026(4) Uiso 0.51 1 d P . . C5B C 0.984(3) 1.1724(11) 0.8677(11) 0.030(4) Uiso 0.49 1 d P . . C6A C 0.935(2) 1.1008(10) 0.9126(10) 0.027(4) Uiso 0.55 1 d P . . C6B C 0.880(3) 1.0871(11) 0.8731(12) 0.020(5) Uiso 0.45 1 d P . . C7 C 1.0063(11) 1.0133(5) 0.8724(4) 0.028(2) Uiso 1 1 d . . . C8A C 1.227(2) 1.0245(10) 0.8725(10) 0.024(4) Uiso 0.49 1 d P . . C8B C 1.183(2) 1.0084(10) 0.8212(10) 0.028(4) Uiso 0.51 1 d P . . C9A C 1.326(2) 1.1063(10) 0.8656(11) 0.017(4) Uiso 0.49 1 d P . . C9B C 1.283(2) 1.0944(11) 0.8206(11) 0.014(7) Uiso 0.46(2) 1 d P . . N10 N 0.9197(10) 0.9241(4) 0.8760(4) 0.0348(18) Uani 1 1 d . . . N11 N 0.7399(11) 0.9243(4) 0.8998(4) 0.0326(18) Uani 1 1 d . . . C12 C 0.6546(11) 0.8363(5) 0.9045(4) 0.027(2) Uani 1 1 d . . . C13A C 0.496(2) 0.8424(10) 0.9539(10) 0.018(4) Uiso 0.49 1 d P . . C13B C 0.423(2) 0.8271(10) 0.9089(10) 0.029(4) Uiso 0.51 1 d P . . C14A C 0.399(2) 0.7584(10) 0.9609(10) 0.019(4) Uiso 0.52 1 d P . . C14B C 0.333(2) 0.7469(10) 0.9212(10) 0.019(4) Uiso 0.48 1 d P . . C15 C 0.4586(10) 0.6723(5) 0.9210(4) 0.029(2) Uani 1 1 d . . . C16A C 0.678(2) 0.6879(9) 0.9217(9) 0.025(4) Uiso 0.51 1 d P . . C16B C 0.629(2) 0.6617(10) 0.8632(10) 0.026(4) Uiso 0.49 1 d P . . C17A C 0.769(2) 0.7688(10) 0.9119(9) 0.018(4) Uiso 0.50 1 d P . . C17B C 0.730(2) 0.7427(10) 0.8560(10) 0.021(4) Uiso 0.50 1 d P . . C18 C 0.3488(13) 0.5823(5) 0.9271(5) 0.034(2) Uani 1 1 d . . . O19 O 0.1793(9) 0.5870(3) 0.9588(3) 0.0319(15) Uani 1 1 d . . . O20A O 0.4518(15) 0.5148(7) 0.9230(7) 0.024(3) Uiso 0.49 1 d P . . O20B O 0.4225(14) 0.4948(7) 0.8748(7) 0.025(3) Uiso 0.51 1 d P . . N21 N 1.1688(8) 0.5621(4) 0.1256(3) 0.0320(18) Uani 1 1 d . . . H21A H 1.2869 0.5328 0.1178 0.048 Uiso 1 1 calc R . . H21B H 1.1652 0.6005 0.0967 0.048 Uiso 1 1 calc R . . H21C H 1.0543 0.5167 0.1056 0.048 Uiso 1 1 calc R . . C22 C 1.1687(15) 0.6241(7) 0.2223(5) 0.079(3) Uani 1 1 d . . . C23B C 1.177(2) 0.5881(12) 0.2799(10) 0.034(4) Uiso 0.51 1 d P . . C23A C 1.226(2) 0.5319(12) 0.2672(9) 0.031(4) Uiso 0.49 1 d P . . C24A C 1.021(3) 0.4562(13) 0.2464(10) 0.034(5) Uiso 0.47 1 d P . . C24B C 0.983(2) 0.5082(12) 0.2683(9) 0.038(4) Uiso 0.53 1 d P . . C25A C 1.050(2) 0.3899(12) 0.2988(10) 0.037(4) Uiso 0.50 1 d P . . C25B C 1.012(2) 0.4587(12) 0.3320(10) 0.040(4) Uiso 0.50 1 d P . . C26B C 0.800(2) 0.3881(11) 0.3175(9) 0.039(4) Uiso 0.53 1 d P . . C26A C 0.833(2) 0.3216(12) 0.2793(10) 0.034(4) Uiso 0.47 1 d P . . C27B C 0.819(2) 0.3253(12) 0.3707(10) 0.039(4) Uiso 0.49 1 d P . . C27A C 0.838(2) 0.2534(12) 0.3296(10) 0.046(4) Uiso 0.51 1 d P . . C28B C 0.601(2) 0.2541(12) 0.3443(10) 0.033(4) Uiso 0.49 1 d P . . C28A C 0.619(2) 0.1902(12) 0.3066(10) 0.040(4) Uiso 0.51 1 d P . . C29A C 0.609(2) 0.1190(12) 0.3537(10) 0.043(4) Uiso 0.50 1 d P . . C29B C 0.610(2) 0.1843(12) 0.3929(10) 0.036(4) Uiso 0.50 1 d P . . C30A C 0.390(2) 0.0580(13) 0.3291(11) 0.037(5) Uiso 0.50 1 d P . . C30B C 0.391(3) 0.1123(13) 0.3619(11) 0.038(5) Uiso 0.50 1 d P . . C31 C 0.3787(14) 0.0144(8) 0.3917(6) 0.081(3) Uani 1 1 d . . . C32 C 0.1568(17) -0.0434(7) 0.3708(5) 0.074(3) Uani 1 1 d . . . H32A H 0.0528 0.0027 0.3893 0.089 Uiso 1 1 calc R . . H32B H 0.1244 -0.0802 0.3079 0.089 Uiso 1 1 calc R . . C33 C 0.1320(15) -0.1141(6) 0.4139(5) 0.063(3) Uani 1 1 d . . . H33A H 0.1633 -0.0769 0.4769 0.075 Uiso 1 1 calc R . . H33B H 0.2383 -0.1591 0.3961 0.075 Uiso 1 1 calc R . . C34 C -0.0880(16) -0.1748(6) 0.3935(5) 0.066(3) Uani 1 1 d . . . H34A H -0.1954 -0.1302 0.4102 0.080 Uiso 1 1 calc R . . H34B H -0.1184 -0.2138 0.3308 0.080 Uiso 1 1 calc R . . C35 C -0.1070(17) -0.2434(7) 0.4402(7) 0.084(3) Uiso 1 1 d . . . C36A C -0.293(3) -0.3148(11) 0.3947(11) 0.038(4) Uiso 0.50 1 d P . . C36B C -0.367(3) -0.2969(12) 0.4339(12) 0.049(5) Uiso 0.50 1 d P . . C37B C -0.383(3) -0.3593(13) 0.4889(12) 0.058(5) Uiso 0.49 1 d P . . C37A C -0.306(3) -0.3881(13) 0.4389(12) 0.064(5) Uiso 0.51 1 d P . . 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 0.025(4) 0.031(3) 0.068(4) 0.023(3) 0.011(3) 0.001(3) C3 0.019(5) 0.027(5) 0.036(5) 0.017(4) 0.007(4) 0.004(4) C4 0.019(5) 0.033(5) 0.020(4) 0.014(4) 0.001(3) -0.002(4) N10 0.025(4) 0.021(4) 0.066(5) 0.027(3) 0.002(4) 0.001(3) N11 0.035(5) 0.025(4) 0.046(4) 0.021(3) 0.016(3) 0.004(3) C12 0.039(5) 0.020(5) 0.028(5) 0.016(4) 0.003(4) 0.000(4) C15 0.019(5) 0.033(5) 0.034(5) 0.017(4) -0.008(4) 0.002(4) C18 0.014(5) 0.039(5) 0.063(6) 0.038(5) -0.007(4) -0.001(4) O19 0.031(3) 0.030(3) 0.033(3) 0.012(2) 0.009(3) -0.002(3) N21 0.021(4) 0.031(4) 0.044(4) 0.017(3) 0.000(3) -0.001(3) C22 0.082(8) 0.092(7) 0.021(5) -0.012(5) 0.019(5) -0.036(6) C31 0.032(6) 0.161(10) 0.093(8) 0.094(8) 0.012(5) 0.009(6) C32 0.102(9) 0.116(8) 0.039(6) 0.056(6) 0.024(5) 0.058(7) C33 0.070(7) 0.060(6) 0.046(6) 0.006(5) 0.001(5) 0.030(6) C34 0.087(8) 0.055(6) 0.041(6) 0.005(5) -0.018(5) 0.028(6) _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 C3 1.206(8) . ? O2A O2B 0.718(11) . ? O2A C3 1.344(10) . ? O2B C3 1.347(12) . ? C3 C4 1.473(9) . ? C4 C5A 1.372(15) . ? C4 C9B 1.387(15) . ? C4 C9A 1.406(15) . ? C4 C5B 1.423(17) . ? C5A C5B 0.736(17) . ? C5A C6A 1.394(18) . ? C5A C6B 1.58(2) . ? C5B C6B 1.43(2) . ? C5B C6A 1.57(2) . ? C6A C6B 0.666(18) . ? C6A C7 1.346(14) . ? C6B C7 1.412(17) . ? C7 C8A 1.392(15) . ? C7 N10 1.427(9) . ? C7 C8B 1.460(15) . ? C8A C8B 0.811(15) . ? C8A C9A 1.378(18) . ? C8A C9B 1.64(2) . ? C8B C9B 1.389(19) . ? C8B C9A 1.52(2) . ? C9A C9B 0.724(16) . ? N10 N11 1.238(8) . ? N11 C12 1.414(9) . ? C12 C17A 1.329(15) . ? C12 C13A 1.345(15) . ? C12 C17B 1.453(14) . ? C12 C13B 1.473(16) . ? C13A C13B 0.789(15) . ? C13A C14A 1.405(18) . ? C13A C14B 1.56(2) . ? C13B C14B 1.383(19) . ? C13B C14A 1.60(2) . ? C14A C14B 0.704(16) . ? C14A C15 1.296(14) . ? C14B C15 1.421(16) . ? C15 C16A 1.384(15) . ? C15 C16B 1.489(15) . ? C15 C18 1.509(10) . ? C16A C16B 0.914(15) . ? C16A C17A 1.374(17) . ? C16A C17B 1.659(19) . ? C16B C17B 1.376(17) . ? C16B C17A 1.614(19) . ? C17A C17B 0.863(14) . ? C18 O20A 1.228(11) . ? C18 O19 1.233(8) . ? C18 O20B 1.396(12) . ? O20A O20B 0.741(10) . ? N21 C22 1.514(9) . ? N21 H21A 0.8900 . ? N21 H21B 0.8900 . ? N21 H21C 0.8900 . ? C22 C23B 1.284(17) . ? C22 C23A 1.865(19) . ? C23B C23A 0.871(16) . ? C23B C24B 1.58(2) . ? C23B C24A 1.97(2) . ? C23A C24B 1.55(2) . ? C23A C24A 1.57(2) . ? C24A C24B 0.784(17) . ? C24A C25B 1.43(2) . ? C24A C25A 1.58(2) . ? C24B C25B 1.53(2) . ? C25A C25B 1.016(16) . ? C25A C26A 1.57(2) . ? C25A C26B 1.64(2) . ? C25B C26B 1.57(2) . ? C26B C26A 0.994(16) . ? C26B C27B 1.54(2) . ? C26A C27B 1.53(2) . ? C26A C27A 1.57(2) . ? C27B C27A 1.043(17) . ? C27B C28B 1.58(2) . ? C27A C28A 1.53(2) . ? C27A C28B 1.54(2) . ? C28B C28A 0.934(16) . ? C28B C29B 1.56(2) . ? C28A C29B 1.50(2) . ? C28A C29A 1.56(2) . ? C29A C29B 0.932(16) . ? C29A C30B 1.40(2) . ? C29A C30A 1.52(2) . ? C29B C30B 1.59(2) . ? C30A C30B 0.777(17) . ? C30A C31 1.449(17) . ? C30B C31 1.727(18) . ? C31 C32 1.520(13) . ? C32 C33 1.509(11) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C34 1.528(11) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.527(12) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C36A 1.446(17) . ? C35 C36B 1.75(2) . ? C36A C36B 0.812(19) . ? C36A C37A 1.55(2) . ? C36B C37A 1.48(2) . ? C36B C37B 1.56(2) . ? C37B C37A 0.97(2) . ? 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 O2B O2A C3 74.8(12) . . ? O2A O2B C3 74.3(12) . . ? O1 C3 O2A 119.9(7) . . ? O1 C3 O2B 120.7(7) . . ? O2A C3 O2B 31.0(5) . . ? O1 C3 C4 123.6(6) . . ? O2A C3 C4 114.3(7) . . ? O2B C3 C4 113.5(7) . . ? C5A C4 C9B 120.7(10) . . ? C5A C4 C9A 110.6(10) . . ? C9B C4 C9A 30.0(7) . . ? C5A C4 C5B 30.5(7) . . ? C9B C4 C5B 112.2(10) . . ? C9A C4 C5B 119.4(9) . . ? C5A C4 C3 121.4(8) . . ? C9B C4 C3 117.8(8) . . ? C9A C4 C3 118.3(8) . . ? C5B C4 C3 122.3(8) . . ? C5B C5A C4 78.6(19) . . ? C5B C5A C6A 89(2) . . ? C4 C5A C6A 120.5(12) . . ? C5B C5A C6B 64.4(18) . . ? C4 C5A C6B 113.2(11) . . ? C6A C5A C6B 24.8(7) . . ? C5A C5B C4 70.9(19) . . ? C5A C5B C6B 88(2) . . ? C4 C5B C6B 120.0(13) . . ? C5A C5B C6A 62.8(18) . . ? C4 C5B C6A 106.8(12) . . ? C6B C5B C6A 25.2(7) . . ? C6B C6A C7 82(2) . . ? C6B C6A C5A 94(2) . . ? C7 C6A C5A 121.3(12) . . ? C6B C6A C5B 66(2) . . ? C7 C6A C5B 112.6(11) . . ? C5A C6A C5B 28.0(7) . . ? C6A C6B C7 71(2) . . ? C6A C6B C5B 89(2) . . ? C7 C6B C5B 117.3(13) . . ? C6A C6B C5A 61(2) . . ? C7 C6B C5A 105.6(12) . . ? C5B C6B C5A 27.7(8) . . ? C6A C7 C8A 111.4(10) . . ? C6A C7 C6B 27.8(7) . . ? C8A C7 C6B 122.3(10) . . ? C6A C7 N10 124.3(8) . . ? C8A C7 N10 115.0(8) . . ? C6B C7 N10 122.6(9) . . ? C6A C7 C8B 118.4(9) . . ? C8A C7 C8B 32.9(6) . . ? C6B C7 C8B 112.1(10) . . ? N10 C7 C8B 117.3(8) . . ? C8B C8A C9A 83.3(18) . . ? C8B C8A C7 78.1(16) . . ? C9A C8A C7 119.6(12) . . ? C8B C8A C9B 57.5(15) . . ? C9A C8A C9B 25.8(7) . . ? C7 C8A C9B 108.0(11) . . ? C8A C8B C9B 93.0(18) . . ? C8A C8B C7 68.9(15) . . ? C9B C8B C7 119.5(12) . . ? C8A C8B C9A 64.6(16) . . ? C9B C8B C9A 28.4(7) . . ? C7 C8B C9A 107.1(11) . . ? C9B C9A C8A 98(2) . . ? C9B C9A C4 73.5(18) . . ? C8A C9A C4 120.9(12) . . ? C9B C9A C8B 66.1(17) . . ? C8A C9A C8B 32.1(7) . . ? C4 C9A C8B 110.2(11) . . ? C9A C9B C4 76.4(18) . . ? C9A C9B C8B 85.5(19) . . ? C4 C9B C8B 119.4(12) . . ? C9A C9B C8A 56.0(17) . . ? C4 C9B C8A 105.7(11) . . ? C8B C9B C8A 29.5(7) . . ? N11 N10 C7 115.5(6) . . ? N10 N11 C12 115.6(6) . . ? C17A C12 C13A 106.6(10) . . ? C17A C12 N11 125.1(8) . . ? C13A C12 N11 117.1(8) . . ? C17A C12 C17B 35.8(6) . . ? C13A C12 C17B 121.1(9) . . ? N11 C12 C17B 121.8(7) . . ? C17A C12 C13B 119.9(9) . . ? C13A C12 C13B 32.1(7) . . ? N11 C12 C13B 114.7(7) . . ? C17B C12 C13B 113.1(9) . . ? C13B C13A C12 82.9(17) . . ? C13B C13A C14A 89.2(18) . . ? C12 C13A C14A 121.0(11) . . ? C13B C13A C14B 62.4(16) . . ? C12 C13A C14B 114.3(11) . . ? C14A C13A C14B 26.8(7) . . ? C13A C13B C14B 87.2(18) . . ? C13A C13B C12 65.0(15) . . ? C14B C13B C12 117.5(12) . . ? C13A C13B C14A 61.3(16) . . ? C14B C13B C14A 26.0(7) . . ? C12 C13B C14A 102.2(10) . . ? C14B C14A C15 85.0(19) . . ? C14B C14A C13A 89(2) . . ? C15 C14A C13A 121.8(12) . . ? C14B C14A C13B 59.4(18) . . ? C15 C14A C13B 113.6(11) . . ? C13A C14A C13B 29.5(7) . . ? C14A C14B C13B 95(2) . . ? C14A C14B C15 65.4(18) . . ? C13B C14B C15 120.2(12) . . ? C14A C14B C13A 64.3(18) . . ? C13B C14B C13A 30.4(7) . . ? C15 C14B C13A 104.7(11) . . ? C14A C15 C16A 106.4(10) . . ? C14A C15 C14B 29.6(7) . . ? C16A C15 C14B 119.2(9) . . ? C14A C15 C16B 118.9(9) . . ? C16A C15 C16B 36.9(6) . . ? C14B C15 C16B 111.6(9) . . ? C14A C15 C18 121.2(8) . . ? C16A C15 C18 122.5(8) . . ? C14B C15 C18 118.1(8) . . ? C16B C15 C18 119.7(8) . . ? C16B C16A C17A 87.3(15) . . ? C16B C16A C15 77.8(14) . . ? C17A C16A C15 120.3(11) . . ? C16B C16A C17B 56.1(13) . . ? C17A C16A C17B 31.3(6) . . ? C15 C16A C17B 109.5(10) . . ? C16A C16B C17B 90.5(16) . . ? C16A C16B C15 65.3(13) . . ? C17B C16B C15 120.7(11) . . ? C16A C16B C17A 58.3(13) . . ? C17B C16B C17A 32.3(7) . . ? C15 C16B C17A 100.8(10) . . ? C17B C17A C12 80.0(14) . . ? C17B C17A C16A 92.9(15) . . ? C12 C17A C16A 122.2(12) . . ? C17B C17A C16B 58.5(13) . . ? C12 C17A C16B 109.2(11) . . ? C16A C17A C16B 34.4(7) . . ? C17A C17B C16B 89.2(16) . . ? C17A C17B C12 64.2(13) . . ? C16B C17B C12 116.4(11) . . ? C17A C17B C16A 55.8(13) . . ? C16B C17B C16A 33.4(7) . . ? C12 C17B C16A 98.8(9) . . ? O20A C18 O19 118.3(8) . . ? O20A C18 O20B 32.0(5) . . ? O19 C18 O20B 124.6(7) . . ? O20A C18 C15 119.3(8) . . ? O19 C18 C15 119.6(7) . . ? O20B C18 C15 113.6(7) . . ? O20B O20A C18 86.6(13) . . ? O20A O20B C18 61.4(11) . . ? C22 N21 H21A 109.5 . . ? C22 N21 H21B 109.5 . . ? H21A N21 H21B 109.5 . . ? C22 N21 H21C 109.5 . . ? H21A N21 H21C 109.5 . . ? H21B N21 H21C 109.5 . . ? C23B C22 N21 123.0(11) . . ? C23B C22 C23A 24.2(8) . . ? N21 C22 C23A 100.0(7) . . ? C23A C23B C22 119(2) . . ? C23A C23B C24B 72.1(16) . . ? C22 C23B C24B 115.4(12) . . ? C23A C23B C24A 50.5(14) . . ? C22 C23B C24A 117.4(11) . . ? C24B C23B C24A 22.3(7) . . ? C23B C23A C24B 75.6(16) . . ? C23B C23A C24A 104.0(18) . . ? C24B C23A C24A 29.1(7) . . ? C23B C23A C22 37.2(13) . . ? C24B C23A C22 90.0(10) . . ? C24A C23A C22 109.2(11) . . ? C24B C24A C25B 82.2(19) . . ? C24B C24A C23A 74.5(18) . . ? C25B C24A C23A 99.0(12) . . ? C24B C24A C25A 121(2) . . ? C25B C24A C25A 39.1(8) . . ? C23A C24A C25A 110.2(12) . . ? C24B C24A C23B 49.9(16) . . ? C25B C24A C23B 98.9(12) . . ? C23A C24A C23B 25.4(7) . . ? C25A C24A C23B 125.1(12) . . ? C24A C24B C25B 67.5(18) . . ? C24A C24B C23A 76.4(19) . . ? C25B C24B C23A 95.2(11) . . ? C24A C24B C23B 108(2) . . ? C25B C24B C23B 113.6(12) . . ? C23A C24B C23B 32.3(7) . . ? C25B C25A C26A 103.9(16) . . ? C25B C25A C24A 62.5(13) . . ? C26A C25A C24A 106.8(12) . . ? C25B C25A C26B 68.0(13) . . ? C26A C25A C26B 36.1(7) . . ? C24A C25A C26B 93.0(11) . . ? C25A C25B C24A 78.4(15) . . ? C25A C25B C24B 108.7(16) . . ? C24A C25B C24B 30.4(8) . . ? C25A C25B C26B 75.1(14) . . ? C24A C25B C26B 102.0(12) . . ? C24B C25B C26B 107.5(11) . . ? C26A C26B C27B 70.4(13) . . ? C26A C26B C25B 104.7(16) . . ? C27B C26B C25B 112.4(11) . . ? C26A C26B C25A 68.1(14) . . ? C27B C26B C25A 95.7(11) . . ? C25B C26B C25A 36.9(7) . . ? C26B C26A C27B 71.8(13) . . ? C26B C26A C25A 75.9(14) . . ? C27B C26A C25A 99.2(11) . . ? C26B C26A C27A 110.9(16) . . ? C27B C26A C27A 39.4(7) . . ? C25A C26A C27A 112.2(12) . . ? C27A C27B C26A 72.4(14) . . ? C27A C27B C26B 110.0(16) . . ? C26A C27B C26B 37.8(7) . . ? C27A C27B C28B 68.2(13) . . ? C26A C27B C28B 95.5(11) . . ? C26B C27B C28B 106.1(12) . . ? C27B C27A C28A 108.1(16) . . ? C27B C27A C28B 72.7(14) . . ? C28A C27A C28B 35.5(7) . . ? C27B C27A C26A 68.2(13) . . ? C28A C27A C26A 108.2(12) . . ? C28B C27A C26A 95.7(12) . . ? C28A C28B C27A 72.0(15) . . ? C28A C28B C29B 68.2(14) . . ? C27A C28B C29B 94.4(12) . . ? C28A C28B C27B 111.1(17) . . ? C27A C28B C27B 39.1(7) . . ? C29B C28B C27B 109.5(12) . . ? C28B C28A C29B 76.3(15) . . ? C28B C28A C27A 72.5(15) . . ? C29B C28A C27A 97.4(12) . . ? C28B C28A C29A 111.4(17) . . ? C29B C28A C29A 35.4(7) . . ? C27A C28A C29A 111.8(12) . . ? C29B C29A C30B 83.5(17) . . ? C29B C29A C30A 114.0(18) . . ? C30B C29A C30A 30.5(8) . . ? C29B C29A C28A 68.3(15) . . ? C30B C29A C28A 99.7(13) . . ? C30A C29A C28A 110.0(12) . . ? C29A C29B C28A 76.3(15) . . ? C29A C29B C28B 111.4(17) . . ? C28A C29B C28B 35.4(7) . . ? C29A C29B C30B 61.0(14) . . ? C28A C29B C30B 94.5(11) . . ? C28B C29B C30B 107.3(12) . . ? C30B C30A C31 97(2) . . ? C30B C30A C29A 66.3(18) . . ? C31 C30A C29A 105.3(12) . . ? C30A C30B C29A 83(2) . . ? C30A C30B C29B 119(2) . . ? C29A C30B C29B 35.5(8) . . ? C30A C30B C31 56.4(17) . . ? C29A C30B C31 97.5(12) . . ? C29B C30B C31 116.2(11) . . ? C30A C31 C32 106.3(9) . . ? C30A C31 C30B 26.5(7) . . ? C32 C31 C30B 113.5(8) . . ? C33 C32 C31 114.0(8) . . ? C33 C32 H32A 108.7 . . ? C31 C32 H32A 108.7 . . ? C33 C32 H32B 108.7 . . ? C31 C32 H32B 108.7 . . ? H32A C32 H32B 107.6 . . ? C32 C33 C34 115.6(8) . . ? C32 C33 H33A 108.4 . . ? C34 C33 H33A 108.4 . . ? C32 C33 H33B 108.4 . . ? C34 C33 H33B 108.4 . . ? H33A C33 H33B 107.4 . . ? C35 C34 C33 113.7(8) . . ? C35 C34 H34A 108.8 . . ? C33 C34 H34A 108.8 . . ? C35 C34 H34B 108.8 . . ? C33 C34 H34B 108.8 . . ? H34A C34 H34B 107.7 . . ? C36A C35 C34 106.3(10) . . ? C36A C35 C36B 27.5(7) . . ? C34 C35 C36B 114.6(9) . . ? C36B C36A C35 97(2) . . ? C36B C36A C37A 69.5(19) . . ? C35 C36A C37A 106.4(12) . . ? C36A C36B C37A 80(2) . . ? C36A C36B C37B 117(2) . . ? C37A C36B C37B 37.2(9) . . ? C36A C36B C35 55.2(16) . . ? C37A C36B C35 96.0(12) . . ? C37B C36B C35 113.2(12) . . ? C37A C37B C36B 67.0(17) . . ? C37B C37A C36B 75.8(18) . . ? C37B C37A C36A 106(2) . . ? C36B C37A C36A 30.9(8) . . ? 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 N21 H21A O20B 0.89 1.92 2.786(10) 163.8 2_766 N21 H21A O20A 0.89 1.92 2.790(11) 163.8 2_766 N21 H21B O19 0.89 2.26 2.982(7) 138.4 1_654 N21 H21C O19 0.89 1.94 2.817(7) 169.6 2_666 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 19.37 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.608 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.085