# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Ip-683-2 #TrackingRef 'IP-683-2_Re-Label.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H25 N3 O2' _chemical_formula_sum 'C21 H25 N3 O2' _chemical_formula_weight 351.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 11.25880(10) _cell_length_b 11.7630(2) _cell_length_c 12.8358(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1699.94(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8004 _cell_measurement_theta_min 3.444 _cell_measurement_theta_max 70.558 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.713 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8705 _exptl_absorpt_correction_T_max 0.9321 _exptl_absorpt_process_details 'SADABS V2.07 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 8778 reflections reduced R(int) from 0.0475 to 0.0277 Ratio of minimum to maximum apparent transmission: 0.817414 The given Tmin and Tmax were generated using the SHELX SIZE command. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 6000' _diffrn_measurement_method 'Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10076 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0241 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 6.44 _diffrn_reflns_theta_max 66.57 _reflns_number_total 2910 _reflns_number_gt 2805 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART V5.626 (Bruker, 1997)' _computing_cell_refinement 'SAINT V6.28A (Bruker, 1997)' _computing_data_reduction 'SAINT V6.28A (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; OLEX2 (Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K, & Puschmann, H., 2009) ; _computing_publication_material 'WinGX (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0537P)^2^+0.3250P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(2) _chemical_absolute_configuration syn _refine_ls_number_reflns 2910 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0344 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0861 _refine_ls_wR_factor_gt 0.0849 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 1.00067(16) 0.26334(15) 0.94610(15) 0.0260(4) Uani 1 1 d . . . H1A H 0.9512 0.2438 0.8849 0.031 Uiso 1 1 calc R . . H1B H 0.9730 0.2190 1.0070 0.031 Uiso 1 1 calc R . . C2 C 1.13239(16) 0.24177(16) 0.92425(16) 0.0301(4) Uani 1 1 d . . . H2A H 1.1510 0.2537 0.8497 0.036 Uiso 1 1 calc R . . H2B H 1.1552 0.1634 0.9440 0.036 Uiso 1 1 calc R . . C3 C 1.19606(15) 0.32939(16) 0.99249(16) 0.0282(4) Uani 1 1 d . . . H3A H 1.2047 0.3011 1.0647 0.034 Uiso 1 1 calc R . . H3B H 1.2758 0.3469 0.9643 0.034 Uiso 1 1 calc R . . C4 C 1.11675(15) 0.43377(15) 0.98926(13) 0.0232(4) Uani 1 1 d . . . C5 C 1.10807(15) 0.50657(16) 1.08850(14) 0.0248(4) Uani 1 1 d . . . H5A H 1.1847 0.5455 1.1012 0.030 Uiso 1 1 calc R . . H5B H 1.0907 0.4574 1.1492 0.030 Uiso 1 1 calc R . . C6 C 1.00766(15) 0.59600(15) 1.07524(12) 0.0204(3) Uani 1 1 d . . . H6 H 1.0473 0.6721 1.0755 0.025 Uiso 1 1 calc R . . C7 C 0.91529(15) 0.59824(15) 1.16476(12) 0.0210(4) Uani 1 1 d . . . C8 C 0.82663(15) 0.69694(14) 1.14194(12) 0.0204(4) Uani 1 1 d . . . H8 H 0.8673 0.7710 1.1558 0.024 Uiso 1 1 calc R . . C10 C 0.63155(15) 0.63318(15) 1.14901(13) 0.0216(4) Uani 1 1 d . . . C11 C 0.52722(15) 0.58346(15) 1.18472(13) 0.0233(4) Uani 1 1 d . . . H11 H 0.5082 0.5837 1.2568 0.028 Uiso 1 1 calc R . . C12 C 0.45151(15) 0.53346(15) 1.11283(14) 0.0243(4) Uani 1 1 d . . . H12 H 0.3812 0.4970 1.1364 0.029 Uiso 1 1 calc R . . C13 C 0.47696(15) 0.53596(14) 1.00703(14) 0.0245(4) Uani 1 1 d . . . H13 H 0.4230 0.5033 0.9586 0.029 Uiso 1 1 calc R . . C14 C 0.58165(15) 0.58639(14) 0.97182(13) 0.0222(4) Uani 1 1 d . . . H14 H 0.5993 0.5882 0.8995 0.027 Uiso 1 1 calc R . . C15 C 0.65936(15) 0.63360(14) 1.04278(13) 0.0202(3) Uani 1 1 d . . . C16 C 0.77386(16) 0.69960(14) 1.02987(13) 0.0199(3) Uani 1 1 d . . . H16 H 0.7491 0.7802 1.0180 0.024 Uiso 1 1 calc R . . C17 C 0.86030(15) 0.67169(14) 0.94091(12) 0.0200(3) Uani 1 1 d . . . H17A H 0.8134 0.6465 0.8799 0.024 Uiso 1 1 calc R . . H17B H 0.9021 0.7424 0.9209 0.024 Uiso 1 1 calc R . . C18 C 0.95282(14) 0.58113(14) 0.96482(12) 0.0186(3) Uani 1 1 d . . . C19 C 0.90849(14) 0.45801(14) 0.94775(12) 0.0174(3) Uani 1 1 d . . . C22 C 1.14393(14) 0.51598(14) 0.89893(12) 0.0209(3) Uani 1 1 d . . . C23 C 0.98091(17) 0.62810(17) 1.26622(13) 0.0274(4) Uani 1 1 d . . . H23A H 1.0383 0.5680 1.2826 0.041 Uiso 1 1 calc R . . H23B H 0.9234 0.6348 1.3232 0.041 Uiso 1 1 calc R . . H23C H 1.0228 0.7005 1.2575 0.041 Uiso 1 1 calc R . . C24 C 0.85206(15) 0.48341(15) 1.17906(12) 0.0223(4) Uani 1 1 d . . . H24A H 0.9113 0.4237 1.1907 0.033 Uiso 1 1 calc R . . H24B H 0.8060 0.4658 1.1164 0.033 Uiso 1 1 calc R . . H24C H 0.7987 0.4876 1.2392 0.033 Uiso 1 1 calc R . . N9 N 0.71798(13) 0.69085(13) 1.20659(11) 0.0233(3) Uani 1 1 d . . . H9 H 0.7094 0.7185 1.2698 0.028 Uiso 1 1 calc R . . N20 N 0.99745(12) 0.38532(12) 0.96736(11) 0.0214(3) Uani 1 1 d . . . N21 N 1.05357(12) 0.59126(12) 0.89038(10) 0.0202(3) Uani 1 1 d . . . H21 H 1.0544 0.6446 0.8423 0.024 Uiso 1 1 calc R . . O19 O 0.80886(10) 0.43123(10) 0.91692(9) 0.0207(3) Uani 1 1 d . . . O22 O 1.23369(10) 0.51410(11) 0.84528(10) 0.0273(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0245(9) 0.0195(8) 0.0339(9) 0.0022(7) 0.0005(8) 0.0019(7) C2 0.0247(9) 0.0235(9) 0.0421(10) -0.0002(8) 0.0018(9) 0.0063(8) C3 0.0192(8) 0.0267(9) 0.0387(10) 0.0051(8) -0.0012(8) 0.0052(7) C4 0.0160(8) 0.0252(9) 0.0283(9) 0.0028(7) -0.0020(7) 0.0001(7) C5 0.0197(8) 0.0295(9) 0.0251(8) 0.0018(7) -0.0042(7) -0.0026(7) C6 0.0191(8) 0.0215(8) 0.0207(8) 0.0011(6) -0.0028(7) -0.0035(7) C7 0.0220(8) 0.0236(9) 0.0174(7) 0.0003(7) -0.0024(7) -0.0037(7) C8 0.0228(8) 0.0200(8) 0.0184(8) 0.0001(6) -0.0001(7) -0.0036(7) C10 0.0207(8) 0.0204(8) 0.0238(8) 0.0010(6) -0.0013(7) 0.0043(7) C11 0.0226(8) 0.0250(8) 0.0223(8) 0.0052(7) 0.0021(7) 0.0029(7) C12 0.0182(8) 0.0223(8) 0.0324(9) 0.0032(7) 0.0003(7) 0.0016(7) C13 0.0210(9) 0.0206(8) 0.0317(9) -0.0026(7) -0.0044(7) 0.0023(7) C14 0.0223(8) 0.0214(8) 0.0229(8) -0.0010(7) -0.0016(7) 0.0054(7) C15 0.0207(8) 0.0172(7) 0.0228(8) 0.0010(6) -0.0003(7) 0.0033(7) C16 0.0222(8) 0.0170(8) 0.0206(8) 0.0020(6) -0.0012(7) 0.0012(7) C17 0.0212(8) 0.0202(8) 0.0186(8) 0.0021(6) -0.0010(7) -0.0014(7) C18 0.0176(7) 0.0192(8) 0.0191(7) 0.0017(6) 0.0013(6) -0.0015(7) C19 0.0175(8) 0.0199(8) 0.0147(7) 0.0009(6) 0.0013(6) 0.0010(6) C22 0.0176(8) 0.0218(8) 0.0233(8) -0.0037(7) -0.0014(7) -0.0023(7) C23 0.0283(9) 0.0318(10) 0.0220(8) -0.0007(7) -0.0033(7) -0.0016(8) C24 0.0227(8) 0.0241(9) 0.0201(8) 0.0039(7) -0.0010(6) -0.0012(7) N9 0.0249(7) 0.0255(7) 0.0194(7) -0.0045(6) 0.0015(6) -0.0015(6) N20 0.0171(7) 0.0199(7) 0.0272(7) 0.0013(6) -0.0006(6) -0.0008(6) N21 0.0199(7) 0.0200(7) 0.0207(7) 0.0026(5) 0.0012(6) -0.0019(6) O19 0.0181(6) 0.0228(6) 0.0211(5) -0.0011(5) -0.0020(5) -0.0016(5) O22 0.0208(6) 0.0307(7) 0.0305(6) -0.0006(5) 0.0034(5) 0.0011(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N20 1.461(2) . ? C1 C2 1.530(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.531(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.519(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N20 1.486(2) . ? C4 C5 1.538(3) . ? C4 C22 1.541(2) . ? C5 C6 1.554(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.550(2) . ? C6 C18 1.556(2) . ? C6 H6 1.0000 . ? C7 C24 1.538(2) . ? C7 C23 1.538(2) . ? C7 C8 1.559(2) . ? C8 N9 1.480(2) . ? C8 C16 1.557(2) . ? C8 H8 1.0000 . ? C10 C11 1.390(2) . ? C10 N9 1.398(2) . ? C10 C15 1.399(2) . ? C11 C12 1.387(3) . ? C11 H11 0.9500 . ? C12 C13 1.388(3) . ? C12 H12 0.9500 . ? C13 C14 1.395(3) . ? C13 H13 0.9500 . ? C14 C15 1.380(2) . ? C14 H14 0.9500 . ? C15 C16 1.514(2) . ? C16 C17 1.536(2) . ? C16 H16 1.0000 . ? C17 C18 1.521(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 N21 1.488(2) . ? C18 C19 1.547(2) . ? C19 O19 1.230(2) . ? C19 N20 1.341(2) . ? C22 O22 1.223(2) . ? C22 N21 1.353(2) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? N9 H9 0.8800 . ? N21 H21 0.8800 . ? 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 N20 C1 C2 102.77(14) . . ? N20 C1 H1A 111.2 . . ? C2 C1 H1A 111.2 . . ? N20 C1 H1B 111.2 . . ? C2 C1 H1B 111.2 . . ? H1A C1 H1B 109.1 . . ? C1 C2 C3 103.73(15) . . ? C1 C2 H2A 111.0 . . ? C3 C2 H2A 111.0 . . ? C1 C2 H2B 111.0 . . ? C3 C2 H2B 111.0 . . ? H2A C2 H2B 109.0 . . ? C4 C3 C2 104.68(14) . . ? C4 C3 H3A 110.8 . . ? C2 C3 H3A 110.8 . . ? C4 C3 H3B 110.8 . . ? C2 C3 H3B 110.8 . . ? H3A C3 H3B 108.9 . . ? N20 C4 C3 103.10(14) . . ? N20 C4 C5 108.23(14) . . ? C3 C4 C5 117.70(15) . . ? N20 C4 C22 106.14(13) . . ? C3 C4 C22 114.28(14) . . ? C5 C4 C22 106.64(13) . . ? C4 C5 C6 109.42(13) . . ? C4 C5 H5A 109.8 . . ? C6 C5 H5A 109.8 . . ? C4 C5 H5B 109.8 . . ? C6 C5 H5B 109.8 . . ? H5A C5 H5B 108.2 . . ? C7 C6 C5 114.74(13) . . ? C7 C6 C18 114.27(13) . . ? C5 C6 C18 108.21(13) . . ? C7 C6 H6 106.3 . . ? C5 C6 H6 106.3 . . ? C18 C6 H6 106.3 . . ? C24 C7 C23 108.78(14) . . ? C24 C7 C6 112.59(14) . . ? C23 C7 C6 108.02(13) . . ? C24 C7 C8 112.35(13) . . ? C23 C7 C8 107.26(14) . . ? C6 C7 C8 107.64(13) . . ? N9 C8 C16 101.76(13) . . ? N9 C8 C7 112.82(13) . . ? C16 C8 C7 115.66(13) . . ? N9 C8 H8 108.8 . . ? C16 C8 H8 108.8 . . ? C7 C8 H8 108.8 . . ? C11 C10 N9 128.19(15) . . ? C11 C10 C15 120.79(16) . . ? N9 C10 C15 110.97(15) . . ? C12 C11 C10 118.58(15) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C11 C12 C13 121.00(16) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C12 C13 C14 120.03(16) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C15 C14 C13 119.54(16) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C10 120.01(16) . . ? C14 C15 C16 132.39(15) . . ? C10 C15 C16 107.40(14) . . ? C15 C16 C17 120.75(14) . . ? C15 C16 C8 102.33(13) . . ? C17 C16 C8 116.16(13) . . ? C15 C16 H16 105.4 . . ? C17 C16 H16 105.4 . . ? C8 C16 H16 105.4 . . ? C18 C17 C16 115.69(13) . . ? C18 C17 H17A 108.4 . . ? C16 C17 H17A 108.4 . . ? C18 C17 H17B 108.4 . . ? C16 C17 H17B 108.4 . . ? H17A C17 H17B 107.4 . . ? N21 C18 C17 109.65(13) . . ? N21 C18 C19 103.29(12) . . ? C17 C18 C19 113.95(13) . . ? N21 C18 C6 105.87(13) . . ? C17 C18 C6 112.14(14) . . ? C19 C18 C6 111.24(12) . . ? O19 C19 N20 125.32(15) . . ? O19 C19 C18 125.39(15) . . ? N20 C19 C18 109.23(14) . . ? O22 C22 N21 125.97(16) . . ? O22 C22 C4 125.20(15) . . ? N21 C22 C4 108.81(13) . . ? C7 C23 H23A 109.5 . . ? C7 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C7 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C7 C24 H24A 109.5 . . ? C7 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C7 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C10 N9 C8 107.60(13) . . ? C10 N9 H9 126.2 . . ? C8 N9 H9 126.2 . . ? C19 N20 C1 127.57(15) . . ? C19 N20 C4 117.79(14) . . ? C1 N20 C4 112.93(14) . . ? C22 N21 C18 117.95(13) . . ? C22 N21 H21 121.0 . . ? C18 N21 H21 121.0 . . ? 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 N20 C1 C2 C3 31.37(19) . . . . ? C1 C2 C3 C4 -36.1(2) . . . . ? C2 C3 C4 N20 25.96(18) . . . . ? C2 C3 C4 C5 144.96(16) . . . . ? C2 C3 C4 C22 -88.75(18) . . . . ? N20 C4 C5 C6 -54.29(17) . . . . ? C3 C4 C5 C6 -170.54(15) . . . . ? C22 C4 C5 C6 59.53(16) . . . . ? C4 C5 C6 C7 127.97(15) . . . . ? C4 C5 C6 C18 -0.93(17) . . . . ? C5 C6 C7 C24 -59.01(18) . . . . ? C18 C6 C7 C24 66.80(18) . . . . ? C5 C6 C7 C23 61.11(18) . . . . ? C18 C6 C7 C23 -173.07(14) . . . . ? C5 C6 C7 C8 176.63(13) . . . . ? C18 C6 C7 C8 -57.55(17) . . . . ? C24 C7 C8 N9 41.40(18) . . . . ? C23 C7 C8 N9 -78.08(17) . . . . ? C6 C7 C8 N9 165.90(13) . . . . ? C24 C7 C8 C16 -75.17(18) . . . . ? C23 C7 C8 C16 165.34(14) . . . . ? C6 C7 C8 C16 49.33(18) . . . . ? N9 C10 C11 C12 177.82(17) . . . . ? C15 C10 C11 C12 0.5(2) . . . . ? C10 C11 C12 C13 -2.1(3) . . . . ? C11 C12 C13 C14 1.9(3) . . . . ? C12 C13 C14 C15 0.0(3) . . . . ? C13 C14 C15 C10 -1.6(3) . . . . ? C13 C14 C15 C16 -175.62(16) . . . . ? C11 C10 C15 C14 1.4(3) . . . . ? N9 C10 C15 C14 -176.42(15) . . . . ? C11 C10 C15 C16 176.76(15) . . . . ? N9 C10 C15 C16 -1.02(19) . . . . ? C14 C15 C16 C17 -35.0(3) . . . . ? C10 C15 C16 C17 150.36(15) . . . . ? C14 C15 C16 C8 -165.97(18) . . . . ? C10 C15 C16 C8 19.42(17) . . . . ? N9 C8 C16 C15 -29.37(15) . . . . ? C7 C8 C16 C15 93.27(16) . . . . ? N9 C8 C16 C17 -163.04(14) . . . . ? C7 C8 C16 C17 -40.4(2) . . . . ? C15 C16 C17 C18 -88.54(19) . . . . ? C8 C16 C17 C18 36.2(2) . . . . ? C16 C17 C18 N21 -160.03(13) . . . . ? C16 C17 C18 C19 84.77(17) . . . . ? C16 C17 C18 C6 -42.72(19) . . . . ? C7 C6 C18 N21 175.19(13) . . . . ? C5 C6 C18 N21 -55.65(15) . . . . ? C7 C6 C18 C17 55.64(18) . . . . ? C5 C6 C18 C17 -175.20(13) . . . . ? C7 C6 C18 C19 -73.29(17) . . . . ? C5 C6 C18 C19 55.88(17) . . . . ? N21 C18 C19 O19 -118.27(17) . . . . ? C17 C18 C19 O19 0.6(2) . . . . ? C6 C18 C19 O19 128.57(16) . . . . ? N21 C18 C19 N20 58.98(15) . . . . ? C17 C18 C19 N20 177.87(14) . . . . ? C6 C18 C19 N20 -54.18(17) . . . . ? N20 C4 C22 O22 -127.07(17) . . . . ? C3 C4 C22 O22 -14.2(2) . . . . ? C5 C4 C22 O22 117.69(18) . . . . ? N20 C4 C22 N21 54.06(16) . . . . ? C3 C4 C22 N21 166.97(14) . . . . ? C5 C4 C22 N21 -61.17(16) . . . . ? C11 C10 N9 C8 163.11(16) . . . . ? C15 C10 N9 C8 -19.32(19) . . . . ? C16 C8 N9 C10 30.23(17) . . . . ? C7 C8 N9 C10 -94.34(16) . . . . ? O19 C19 N20 C1 7.4(3) . . . . ? C18 C19 N20 C1 -169.90(15) . . . . ? O19 C19 N20 C4 171.30(15) . . . . ? C18 C19 N20 C4 -5.96(19) . . . . ? C2 C1 N20 C19 148.68(17) . . . . ? C2 C1 N20 C4 -15.91(19) . . . . ? C3 C4 N20 C19 -172.49(14) . . . . ? C5 C4 N20 C19 62.12(18) . . . . ? C22 C4 N20 C19 -52.03(18) . . . . ? C3 C4 N20 C1 -6.25(19) . . . . ? C5 C4 N20 C1 -131.64(15) . . . . ? C22 C4 N20 C1 114.20(15) . . . . ? O22 C22 N21 C18 -178.62(16) . . . . ? C4 C22 N21 C18 0.23(19) . . . . ? C17 C18 N21 C22 -178.99(13) . . . . ? C19 C18 N21 C22 -57.17(17) . . . . ? C6 C18 N21 C22 59.84(17) . . . . ? 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 N9 H9 O19 0.88 2.59 3.0728(19) 115.4 2_665 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 66.57 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.362 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 848586' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_16b #EPSRC UK National Crystallography Code: 2011ncs0271a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H25 N3 O2, C H4 O' _chemical_formula_sum 'C22 H29 N3 O3' _chemical_formula_weight 383.48 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 8.0470(17) _cell_length_b 10.678(3) _cell_length_c 22.331(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1918.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6511 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.6 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9894 _exptl_absorpt_correction_T_max 0.9991 _exptl_absorpt_process_details ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_detector CCD _diffrn_measurement_device ; AFC12 (Right): Kappa 3 circle ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14736 _diffrn_reflns_av_R_equivalents 0.0754 _diffrn_reflns_av_sigmaI/netI 0.0623 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2518 _reflns_number_gt 2262 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; OLEX2 (Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K, & Puschmann, H., 2009) ; _computing_publication_material 'WinGX (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0490P)^2^+0.5234P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack ? _chemical_absolute_configuration syn _refine_ls_number_reflns 2518 _refine_ls_number_parameters 267 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0727 _refine_ls_R_factor_gt 0.0628 _refine_ls_wR_factor_ref 0.1319 _refine_ls_wR_factor_gt 0.1275 _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_restrained_S_all 1.139 _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 0.1283(5) 0.9973(3) 0.92296(15) 0.0326(9) Uani 0.739(12) 1 d PD A 1 H1A H 0.0148 1.0200 0.9097 0.039 Uiso 0.739(12) 1 calc PR A 1 H1B H 0.2009 1.0719 0.9200 0.039 Uiso 0.739(12) 1 calc PR A 1 C2 C 0.1268(9) 0.9465(6) 0.9850(2) 0.0354(18) Uani 0.739(12) 1 d PD A 1 H2A H 0.0218 0.9012 0.9930 0.042 Uiso 0.739(12) 1 calc PR A 1 H2B H 0.1389 1.0148 1.0147 0.042 Uiso 0.739(12) 1 calc PR A 1 C3 C 0.2773(5) 0.8559(3) 0.98801(14) 0.0287(8) Uani 0.739(12) 1 d PD A 1 H3A H 0.3786 0.9006 1.0012 0.034 Uiso 0.739(12) 1 calc PR A 1 H3B H 0.2550 0.7862 1.0162 0.034 Uiso 0.739(12) 1 calc PR A 1 C1' C 0.1283(5) 0.9973(3) 0.92296(15) 0.0326(9) Uani 0.261(12) 1 d PD A 2 H1C H 0.0084 0.9861 0.9314 0.039 Uiso 0.261(12) 1 calc PR A 2 H1D H 0.1454 1.0783 0.9023 0.039 Uiso 0.261(12) 1 calc PR A 2 C2' C 0.2321(18) 0.9893(9) 0.9806(4) 0.018(4) Uani 0.261(12) 1 d PD A 2 H2C H 0.3332 1.0416 0.9771 0.021 Uiso 0.261(12) 1 calc PR A 2 H2D H 0.1666 1.0188 1.0153 0.021 Uiso 0.261(12) 1 calc PR A 2 C3' C 0.2773(5) 0.8559(3) 0.98801(14) 0.0287(8) Uani 0.261(12) 1 d PD A 2 H3C H 0.1884 0.8097 1.0093 0.034 Uiso 0.261(12) 1 calc PR A 2 H3D H 0.3822 0.8474 1.0108 0.034 Uiso 0.261(12) 1 calc PR A 2 C4 C 0.2979(4) 0.8070(3) 0.92452(14) 0.0226(7) Uani 1 1 d . . . C5 C 0.4742(4) 0.8111(3) 0.89876(13) 0.0225(7) Uani 1 1 d . A . H5A H 0.5437 0.7463 0.9183 0.027 Uiso 1 1 calc R . . H5B H 0.5248 0.8939 0.9068 0.027 Uiso 1 1 calc R . . C6 C 0.4683(4) 0.7875(3) 0.83048(13) 0.0202(7) Uani 1 1 d . . . H6 H 0.4922 0.8698 0.8109 0.024 Uiso 1 1 calc R A . C7 C 0.6009(4) 0.6955(3) 0.80750(14) 0.0210(7) Uani 1 1 d . A . C8 C 0.5762(4) 0.6697(3) 0.74088(14) 0.0223(7) Uani 1 1 d . . . H8 H 0.6537 0.6007 0.7292 0.027 Uiso 1 1 calc R A . N9 N 0.6052(4) 0.7766(2) 0.69972(11) 0.0229(6) Uani 1 1 d . A . H9 H 0.6583 0.8467 0.7077 0.027 Uiso 1 1 calc R . . C10 C 0.5305(4) 0.7426(3) 0.64547(15) 0.0238(7) Uani 1 1 d . . . C11 C 0.5609(5) 0.7887(3) 0.58835(14) 0.0276(8) Uani 1 1 d . A . H11 H 0.6402 0.8531 0.5816 0.033 Uiso 1 1 calc R . . C12 C 0.4697(5) 0.7362(3) 0.54115(15) 0.0333(9) Uani 1 1 d . . . H12 H 0.4895 0.7648 0.5015 0.040 Uiso 1 1 calc R A . C13 C 0.3518(5) 0.6441(3) 0.55061(16) 0.0317(9) Uani 1 1 d . A . H13 H 0.2931 0.6093 0.5177 0.038 Uiso 1 1 calc R . . C14 C 0.3192(5) 0.6021(3) 0.60861(15) 0.0262(8) Uani 1 1 d . . . H14 H 0.2359 0.5408 0.6155 0.031 Uiso 1 1 calc R A . C15 C 0.4092(4) 0.6506(3) 0.65572(14) 0.0228(7) Uani 1 1 d . A . C16 C 0.3980(4) 0.6300(3) 0.72269(13) 0.0222(7) Uani 1 1 d . A . H16 H 0.3740 0.5407 0.7331 0.027 Uiso 1 1 calc R . . C17 C 0.2667(4) 0.7200(3) 0.74788(14) 0.0235(7) Uani 1 1 d . . . H17A H 0.2702 0.7984 0.7243 0.028 Uiso 1 1 calc R A . H17B H 0.1557 0.6820 0.7419 0.028 Uiso 1 1 calc R . . C18 C 0.2851(4) 0.7529(3) 0.81336(14) 0.0198(7) Uani 1 1 d . A . C19 C 0.1845(4) 0.8718(3) 0.82926(14) 0.0223(7) Uani 1 1 d . . . O19 O 0.1077(3) 0.9382(2) 0.79299(10) 0.0261(5) Uani 1 1 d . A . N20 N 0.1945(4) 0.8930(3) 0.88784(12) 0.0255(7) Uani 1 1 d . A . N21 N 0.2264(3) 0.6532(3) 0.85353(12) 0.0228(6) Uani 1 1 d . . . H21A H 0.1896 0.5815 0.8392 0.027 Uiso 1 1 calc R A . C22 C 0.2307(4) 0.6751(3) 0.91311(15) 0.0248(7) Uani 1 1 d . A . O22 O 0.1926(3) 0.5998(2) 0.95225(11) 0.0364(7) Uani 1 1 d . . . C23 C 0.7746(4) 0.7531(3) 0.81755(15) 0.0281(8) Uani 1 1 d . . . H23A H 0.7806 0.8348 0.7977 0.042 Uiso 1 1 calc R A . H23B H 0.8595 0.6973 0.8008 0.042 Uiso 1 1 calc R . . H23C H 0.7941 0.7637 0.8606 0.042 Uiso 1 1 calc R . . C24 C 0.5968(5) 0.5666(3) 0.83864(15) 0.0290(8) Uani 1 1 d . . . H24A H 0.6870 0.5142 0.8231 0.044 Uiso 1 1 calc R A . H24B H 0.4899 0.5259 0.8307 0.044 Uiso 1 1 calc R . . H24C H 0.6110 0.5778 0.8819 0.044 Uiso 1 1 calc R . . C101 C -0.0101(5) 0.3629(4) 0.86621(15) 0.0312(9) Uani 1 1 d . . . H10A H 0.0131 0.2729 0.8651 0.047 Uiso 1 1 calc R . . H10B H -0.1305 0.3766 0.8655 0.047 Uiso 1 1 calc R . . H10C H 0.0365 0.3990 0.9029 0.047 Uiso 1 1 calc R . . O101 O 0.0643(3) 0.4222(2) 0.81502(10) 0.0276(6) Uani 1 1 d . . . H101 H 0.0004 0.4155 0.7854 0.041 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 0.035(2) 0.031(2) 0.032(2) -0.0115(16) -0.0023(16) 0.0062(18) C2 0.047(4) 0.033(3) 0.026(3) 0.001(2) 0.007(2) 0.009(3) C3 0.028(2) 0.034(2) 0.0239(18) -0.0038(14) 0.0013(14) -0.0043(18) C1' 0.035(2) 0.031(2) 0.032(2) -0.0115(16) -0.0023(16) 0.0062(18) C2' 0.014(8) 0.027(7) 0.013(6) -0.008(5) -0.001(5) -0.003(6) C3' 0.028(2) 0.034(2) 0.0239(18) -0.0038(14) 0.0013(14) -0.0043(18) C4 0.0234(18) 0.0250(17) 0.0194(16) -0.0002(13) 0.0012(13) 0.0014(15) C5 0.0234(17) 0.0229(17) 0.0212(16) -0.0008(13) 0.0000(13) -0.0018(15) C6 0.0210(17) 0.0192(16) 0.0203(16) 0.0014(12) -0.0012(12) -0.0044(15) C7 0.0200(16) 0.0195(16) 0.0235(16) 0.0017(12) -0.0008(13) 0.0029(14) C8 0.0264(18) 0.0187(17) 0.0218(17) 0.0002(12) -0.0015(13) 0.0026(15) N9 0.0315(16) 0.0172(14) 0.0199(14) 0.0013(10) -0.0018(11) -0.0019(13) C10 0.0250(18) 0.0223(17) 0.0240(17) -0.0028(13) -0.0006(13) 0.0057(16) C11 0.033(2) 0.0258(18) 0.0242(17) 0.0005(13) 0.0021(14) -0.0002(17) C12 0.049(2) 0.030(2) 0.0211(18) -0.0012(14) -0.0014(15) 0.008(2) C13 0.039(2) 0.0264(19) 0.0293(19) -0.0082(15) -0.0092(16) 0.0094(18) C14 0.030(2) 0.0204(17) 0.0283(18) -0.0024(13) -0.0052(14) 0.0015(16) C15 0.0275(19) 0.0172(16) 0.0238(17) -0.0016(12) -0.0001(13) 0.0056(15) C16 0.0254(18) 0.0189(16) 0.0223(16) -0.0009(12) -0.0037(13) 0.0001(15) C17 0.0241(18) 0.0210(17) 0.0253(17) -0.0004(13) -0.0021(13) -0.0026(15) C18 0.0175(16) 0.0204(16) 0.0215(16) 0.0013(12) 0.0002(12) 0.0000(14) C19 0.0177(17) 0.0230(17) 0.0263(17) -0.0018(13) 0.0016(13) -0.0012(15) O19 0.0261(13) 0.0258(13) 0.0265(12) 0.0019(10) -0.0031(10) 0.0053(12) N20 0.0272(16) 0.0264(15) 0.0230(14) -0.0027(11) -0.0014(12) 0.0060(14) N21 0.0250(15) 0.0186(14) 0.0250(14) 0.0027(11) 0.0002(12) -0.0054(13) C22 0.0216(18) 0.0267(18) 0.0261(17) 0.0048(13) 0.0007(13) -0.0036(16) O22 0.0427(17) 0.0391(16) 0.0273(13) 0.0075(11) 0.0015(12) -0.0107(14) C23 0.0246(19) 0.034(2) 0.0260(18) -0.0025(14) -0.0024(14) 0.0035(17) C24 0.038(2) 0.0210(17) 0.0285(18) 0.0047(14) -0.0025(15) 0.0106(18) C101 0.032(2) 0.032(2) 0.0296(19) 0.0072(15) -0.0023(16) -0.0027(18) O101 0.0305(14) 0.0273(13) 0.0251(12) -0.0013(10) -0.0064(10) -0.0073(12) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N20 1.463(4) . ? C1 C2 1.488(5) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.551(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.520(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C2' H2C 0.9900 . ? C2' H2D 0.9900 . ? C4 N20 1.485(4) . ? C4 C22 1.530(5) . ? C4 C5 1.532(5) . ? C5 C6 1.546(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.539(4) . ? C6 C18 1.567(4) . ? C6 H6 1.0000 . ? C7 C8 1.526(4) . ? C7 C24 1.542(4) . ? C7 C23 1.543(5) . ? C8 N9 1.484(4) . ? C8 C16 1.549(5) . ? C8 H8 1.0000 . ? N9 C10 1.400(4) . ? N9 H9 0.8800 . ? C10 C11 1.389(4) . ? C10 C15 1.404(5) . ? C11 C12 1.401(5) . ? C11 H11 0.9500 . ? C12 C13 1.383(5) . ? C12 H12 0.9500 . ? C13 C14 1.395(5) . ? C13 H13 0.9500 . ? C14 C15 1.378(4) . ? C14 H14 0.9500 . ? C15 C16 1.514(4) . ? C16 C17 1.535(5) . ? C16 H16 1.0000 . ? C17 C18 1.511(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 N21 1.470(4) . ? C18 C19 1.548(4) . ? C19 O19 1.241(4) . ? C19 N20 1.330(4) . ? N21 C22 1.351(4) . ? N21 H21A 0.8800 . ? C22 O22 1.226(4) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C101 O101 1.437(4) . ? C101 H10A 0.9800 . ? C101 H10B 0.9800 . ? C101 H10C 0.9800 . ? O101 H101 0.8400 . ? 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 N20 C1 C2 102.9(3) . . ? N20 C1 H1A 111.2 . . ? C2 C1 H1A 111.2 . . ? N20 C1 H1B 111.2 . . ? C2 C1 H1B 111.2 . . ? H1A C1 H1B 109.1 . . ? C1 C2 C3 105.2(4) . . ? C1 C2 H2A 110.7 . . ? C3 C2 H2A 110.7 . . ? C1 C2 H2B 110.7 . . ? C3 C2 H2B 110.7 . . ? H2A C2 H2B 108.8 . . ? C4 C3 C2 105.0(3) . . ? C4 C3 H3A 110.8 . . ? C2 C3 H3A 110.8 . . ? C4 C3 H3B 110.8 . . ? C2 C3 H3B 110.8 . . ? H3A C3 H3B 108.8 . . ? H2C C2' H2D 108.6 . . ? N20 C4 C3 104.0(3) . . ? N20 C4 C22 106.2(3) . . ? C3 C4 C22 115.6(3) . . ? N20 C4 C5 107.1(3) . . ? C3 C4 C5 116.2(3) . . ? C22 C4 C5 106.9(3) . . ? C4 C5 C6 109.7(3) . . ? C4 C5 H5A 109.7 . . ? C6 C5 H5A 109.7 . . ? C4 C5 H5B 109.7 . . ? C6 C5 H5B 109.7 . . ? H5A C5 H5B 108.2 . . ? C7 C6 C5 114.3(3) . . ? C7 C6 C18 114.9(3) . . ? C5 C6 C18 107.9(3) . . ? C7 C6 H6 106.4 . . ? C5 C6 H6 106.4 . . ? C18 C6 H6 106.4 . . ? C8 C7 C6 110.5(3) . . ? C8 C7 C24 106.0(3) . . ? C6 C7 C24 113.9(3) . . ? C8 C7 C23 109.4(3) . . ? C6 C7 C23 109.0(3) . . ? C24 C7 C23 108.0(3) . . ? N9 C8 C7 116.4(3) . . ? N9 C8 C16 101.2(3) . . ? C7 C8 C16 115.2(3) . . ? N9 C8 H8 107.8 . . ? C7 C8 H8 107.8 . . ? C16 C8 H8 107.8 . . ? C10 N9 C8 105.6(3) . . ? C10 N9 H9 127.2 . . ? C8 N9 H9 127.2 . . ? C11 C10 N9 128.8(3) . . ? C11 C10 C15 121.4(3) . . ? N9 C10 C15 109.8(3) . . ? C10 C11 C12 117.2(3) . . ? C10 C11 H11 121.4 . . ? C12 C11 H11 121.4 . . ? C13 C12 C11 121.9(3) . . ? C13 C12 H12 119.0 . . ? C11 C12 H12 119.0 . . ? C12 C13 C14 119.9(3) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C15 C14 C13 119.3(3) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C10 120.2(3) . . ? C14 C15 C16 131.9(3) . . ? C10 C15 C16 107.7(3) . . ? C15 C16 C17 108.2(3) . . ? C15 C16 C8 99.5(3) . . ? C17 C16 C8 111.7(3) . . ? C15 C16 H16 112.3 . . ? C17 C16 H16 112.3 . . ? C8 C16 H16 112.3 . . ? C18 C17 C16 115.6(3) . . ? C18 C17 H17A 108.4 . . ? C16 C17 H17A 108.4 . . ? C18 C17 H17B 108.4 . . ? C16 C17 H17B 108.4 . . ? H17A C17 H17B 107.4 . . ? N21 C18 C17 113.0(3) . . ? N21 C18 C19 106.6(2) . . ? C17 C18 C19 111.2(3) . . ? N21 C18 C6 108.9(3) . . ? C17 C18 C6 112.5(3) . . ? C19 C18 C6 104.0(3) . . ? O19 C19 N20 125.1(3) . . ? O19 C19 C18 125.4(3) . . ? N20 C19 C18 109.5(3) . . ? C19 N20 C1 129.4(3) . . ? C19 N20 C4 118.1(3) . . ? C1 N20 C4 112.3(3) . . ? C22 N21 C18 117.9(3) . . ? C22 N21 H21A 121.1 . . ? C18 N21 H21A 121.1 . . ? O22 C22 N21 125.6(3) . . ? O22 C22 C4 125.0(3) . . ? N21 C22 C4 109.4(3) . . ? C7 C23 H23A 109.5 . . ? C7 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C7 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C7 C24 H24A 109.5 . . ? C7 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C7 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O101 C101 H10A 109.5 . . ? O101 C101 H10B 109.5 . . ? H10A C101 H10B 109.5 . . ? O101 C101 H10C 109.5 . . ? H10A C101 H10C 109.5 . . ? H10B C101 H10C 109.5 . . ? C101 O101 H101 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 N20 C1 C2 C3 32.4(5) . . . . ? C1 C2 C3 C4 -29.4(6) . . . . ? C2 C3 C4 N20 14.1(4) . . . . ? C2 C3 C4 C22 -101.9(4) . . . . ? C2 C3 C4 C5 131.5(4) . . . . ? N20 C4 C5 C6 -51.5(3) . . . . ? C3 C4 C5 C6 -167.2(3) . . . . ? C22 C4 C5 C6 62.0(3) . . . . ? C4 C5 C6 C7 -135.4(3) . . . . ? C4 C5 C6 C18 -6.3(4) . . . . ? C5 C6 C7 C8 175.2(3) . . . . ? C18 C6 C7 C8 49.7(4) . . . . ? C5 C6 C7 C24 56.1(4) . . . . ? C18 C6 C7 C24 -69.5(3) . . . . ? C5 C6 C7 C23 -64.6(3) . . . . ? C18 C6 C7 C23 169.9(3) . . . . ? C6 C7 C8 N9 66.8(3) . . . . ? C24 C7 C8 N9 -169.4(3) . . . . ? C23 C7 C8 N9 -53.2(4) . . . . ? C6 C7 C8 C16 -51.5(4) . . . . ? C24 C7 C8 C16 72.4(3) . . . . ? C23 C7 C8 C16 -171.4(3) . . . . ? C7 C8 N9 C10 -163.4(3) . . . . ? C16 C8 N9 C10 -37.7(3) . . . . ? C8 N9 C10 C11 -159.0(3) . . . . ? C8 N9 C10 C15 22.1(4) . . . . ? N9 C10 C11 C12 178.9(3) . . . . ? C15 C10 C11 C12 -2.3(5) . . . . ? C10 C11 C12 C13 1.2(5) . . . . ? C11 C12 C13 C14 0.9(6) . . . . ? C12 C13 C14 C15 -2.0(5) . . . . ? C13 C14 C15 C10 1.0(5) . . . . ? C13 C14 C15 C16 176.5(3) . . . . ? C11 C10 C15 C14 1.2(5) . . . . ? N9 C10 C15 C14 -179.7(3) . . . . ? C11 C10 C15 C16 -175.2(3) . . . . ? N9 C10 C15 C16 3.8(4) . . . . ? C14 C15 C16 C17 -85.5(4) . . . . ? C10 C15 C16 C17 90.4(3) . . . . ? C14 C15 C16 C8 157.8(4) . . . . ? C10 C15 C16 C8 -26.3(3) . . . . ? N9 C8 C16 C15 37.8(3) . . . . ? C7 C8 C16 C15 164.2(3) . . . . ? N9 C8 C16 C17 -76.2(3) . . . . ? C7 C8 C16 C17 50.3(4) . . . . ? C15 C16 C17 C18 -155.8(3) . . . . ? C8 C16 C17 C18 -47.3(4) . . . . ? C16 C17 C18 N21 -77.7(4) . . . . ? C16 C17 C18 C19 162.5(3) . . . . ? C16 C17 C18 C6 46.2(4) . . . . ? C7 C6 C18 N21 78.4(3) . . . . ? C5 C6 C18 N21 -50.4(3) . . . . ? C7 C6 C18 C17 -47.7(4) . . . . ? C5 C6 C18 C17 -176.5(3) . . . . ? C7 C6 C18 C19 -168.2(2) . . . . ? C5 C6 C18 C19 63.1(3) . . . . ? N21 C18 C19 O19 -128.5(3) . . . . ? C17 C18 C19 O19 -4.9(5) . . . . ? C6 C18 C19 O19 116.4(4) . . . . ? N21 C18 C19 N20 52.2(3) . . . . ? C17 C18 C19 N20 175.8(3) . . . . ? C6 C18 C19 N20 -62.8(3) . . . . ? O19 C19 N20 C1 -3.1(6) . . . . ? C18 C19 N20 C1 176.2(3) . . . . ? O19 C19 N20 C4 -177.4(3) . . . . ? C18 C19 N20 C4 1.9(4) . . . . ? C2 C1 N20 C19 160.8(5) . . . . ? C2 C1 N20 C4 -24.7(5) . . . . ? C3 C4 N20 C19 -178.5(3) . . . . ? C22 C4 N20 C19 -56.1(4) . . . . ? C5 C4 N20 C19 57.9(4) . . . . ? C3 C4 N20 C1 6.3(4) . . . . ? C22 C4 N20 C1 128.7(3) . . . . ? C5 C4 N20 C1 -117.3(3) . . . . ? C17 C18 N21 C22 -177.3(3) . . . . ? C19 C18 N21 C22 -54.8(4) . . . . ? C6 C18 N21 C22 56.9(4) . . . . ? C18 N21 C22 O22 -176.9(3) . . . . ? C18 N21 C22 C4 0.7(4) . . . . ? N20 C4 C22 O22 -129.2(4) . . . . ? C3 C4 C22 O22 -14.5(5) . . . . ? C5 C4 C22 O22 116.6(4) . . . . ? N20 C4 C22 N21 53.2(3) . . . . ? C3 C4 C22 N21 167.9(3) . . . . ? C5 C4 C22 N21 -61.0(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N9 H9 O101 0.88 2.43 3.098(4) 133.3 3_656 N21 H21A O101 0.88 2.05 2.920(4) 169.2 . O101 H101 O19 0.84 1.97 2.786(3) 163.5 3_546 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.314 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 936851' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_14a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H45 N3 O5 S, C H4 O' _chemical_formula_sum 'C41 H49 N3 O6 S' _chemical_formula_weight 711.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 10.6567(3) _cell_length_b 13.9156(4) _cell_length_c 24.7451(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3669.56(17) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9179 _cell_measurement_theta_min 3.176 _cell_measurement_theta_max 71.030 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 1.202 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6853 _exptl_absorpt_correction_T_max 0.7612 _exptl_absorpt_process_details 'SADABS V2.07 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 28046 reflections reduced R(int) from 0.0406 to 0.0286 Ratio of minimum to maximum apparent transmission: 0.912072 The given Tmin and Tmax were generated using the SHELX SIZE command. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 6000' _diffrn_measurement_method 'Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28682 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 6.34 _diffrn_reflns_theta_max 68.22 _reflns_number_total 6618 _reflns_number_gt 6516 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART V5.626 (Bruker, 1997)' _computing_cell_refinement 'SAINT V6.28A (Bruker, 1997)' _computing_data_reduction 'SAINT V6.28A (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; OLEX2 (Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K, & Puschmann, H., 2009) ; _computing_publication_material 'WinGX (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.9997P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.020(13) _chemical_absolute_configuration ad _refine_ls_number_reflns 6618 _refine_ls_number_parameters 467 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0336 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.0925 _refine_ls_wR_factor_gt 0.0921 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.58998(18) 0.70476(14) 0.12282(8) 0.0335(4) Uani 1 1 d . . . H1A H 0.5605 0.7601 0.1445 0.040 Uiso 1 1 calc R . . H1B H 0.5337 0.6494 0.1294 0.040 Uiso 1 1 calc R . . C2 C 0.59442(19) 0.73013(14) 0.06280(8) 0.0359(4) Uani 1 1 d . . . H2A H 0.5409 0.7866 0.0549 0.043 Uiso 1 1 calc R . . H2B H 0.5661 0.6753 0.0404 0.043 Uiso 1 1 calc R . . C3 C 0.73275(19) 0.75287(13) 0.05223(7) 0.0323(4) Uani 1 1 d . . . H3A H 0.7547 0.7426 0.0138 0.039 Uiso 1 1 calc R . . H3B H 0.7530 0.8199 0.0623 0.039 Uiso 1 1 calc R . . C4 C 0.80055(17) 0.68168(12) 0.08855(7) 0.0251(3) Uani 1 1 d . . . C5 C 0.80121(18) 0.57825(12) 0.06353(7) 0.0273(4) Uani 1 1 d . . . H5A H 0.8363 0.5331 0.0905 0.033 Uiso 1 1 calc R . . H5B H 0.7134 0.5587 0.0565 0.033 Uiso 1 1 calc R . . C6 C 0.87413(19) 0.56845(13) 0.01236(7) 0.0318(4) Uani 1 1 d . . . H6 H 0.9629 0.5712 0.0153 0.038 Uiso 1 1 calc R . . C7 C 0.8274(2) 0.55633(13) -0.03695(8) 0.0379(4) Uani 1 1 d . . . C8 C 0.96847(17) 0.44865(12) 0.16481(7) 0.0265(4) Uani 1 1 d . . . H8 H 1.0381 0.4758 0.1463 0.032 Uiso 1 1 calc R . . C10 C 0.81447(17) 0.34443(12) 0.18871(7) 0.0264(3) Uani 1 1 d . . . C11 C 0.73409(18) 0.26638(13) 0.19451(8) 0.0309(4) Uani 1 1 d . . . H11 H 0.7385 0.2126 0.1709 0.037 Uiso 1 1 calc R . . C12 C 0.64769(18) 0.27038(14) 0.23594(8) 0.0341(4) Uani 1 1 d . . . H12 H 0.5904 0.2187 0.2407 0.041 Uiso 1 1 calc R . . C13 C 0.6428(2) 0.34842(14) 0.27083(8) 0.0353(4) Uani 1 1 d . . . H13 H 0.5826 0.3487 0.2991 0.042 Uiso 1 1 calc R . . C14 C 0.72333(18) 0.42571(14) 0.26542(7) 0.0314(4) Uani 1 1 d . . . H14 H 0.7188 0.4789 0.2894 0.038 Uiso 1 1 calc R . . C15 C 0.81134(17) 0.42344(12) 0.22383(7) 0.0268(4) Uani 1 1 d . . . C16 C 0.91006(17) 0.48847(12) 0.20755(6) 0.0243(3) Uani 1 1 d . . . C17 C 0.93888(18) 0.58359(12) 0.23345(7) 0.0277(4) Uani 1 1 d . . . H17A H 1.0303 0.5877 0.2402 0.033 Uiso 1 1 calc R . . H17B H 0.8959 0.5869 0.2689 0.033 Uiso 1 1 calc R . . C18 C 0.89838(17) 0.67052(12) 0.19903(7) 0.0253(4) Uani 1 1 d . . . C19 C 0.75745(17) 0.66449(12) 0.18647(7) 0.0259(4) Uani 1 1 d . . . C22 C 0.93349(17) 0.70956(12) 0.10180(6) 0.0254(3) Uani 1 1 d . . . C23 C 0.9130(3) 0.54601(18) -0.08476(9) 0.0582(7) Uani 1 1 d . . . H23A H 1.0005 0.5477 -0.0726 0.087 Uiso 1 1 calc R . . H23B H 0.8981 0.5989 -0.1101 0.087 Uiso 1 1 calc R . . H23C H 0.8964 0.4847 -0.1028 0.087 Uiso 1 1 calc R . . C24 C 0.6908(2) 0.55289(15) -0.05029(9) 0.0452(5) Uani 1 1 d . . . H24A H 0.6427 0.5382 -0.0175 0.068 Uiso 1 1 calc R . . H24B H 0.6758 0.5029 -0.0774 0.068 Uiso 1 1 calc R . . H24C H 0.6642 0.6153 -0.0647 0.068 Uiso 1 1 calc R . . C25 C 0.93719(17) 0.30472(12) 0.10645(7) 0.0288(4) Uani 1 1 d . . . C27 C 1.0778(2) 0.29816(14) 0.02850(8) 0.0355(4) Uani 1 1 d . . . C28 C 1.1175(2) 0.19470(15) 0.03738(10) 0.0474(5) Uani 1 1 d . . . H28A H 1.1689 0.1904 0.0701 0.071 Uiso 1 1 calc R . . H28B H 1.1664 0.1725 0.0062 0.071 Uiso 1 1 calc R . . H28C H 1.0428 0.1543 0.0415 0.071 Uiso 1 1 calc R . . C29 C 1.1874(2) 0.36173(15) 0.01449(9) 0.0417(5) Uani 1 1 d . . . H29A H 1.1581 0.4279 0.0096 0.063 Uiso 1 1 calc R . . H29B H 1.2263 0.3390 -0.0190 0.063 Uiso 1 1 calc R . . H29C H 1.2492 0.3596 0.0438 0.063 Uiso 1 1 calc R . . C30 C 0.9752(2) 0.30641(18) -0.01325(8) 0.0458(5) Uani 1 1 d . . . H30A H 0.9061 0.2632 -0.0037 0.069 Uiso 1 1 calc R . . H30B H 1.0085 0.2886 -0.0488 0.069 Uiso 1 1 calc R . . H30C H 0.9445 0.3728 -0.0144 0.069 Uiso 1 1 calc R . . C32 C 0.84775(19) 0.86881(12) 0.20411(7) 0.0303(4) Uani 1 1 d . . . C33 C 0.7219(2) 0.89334(14) 0.21011(8) 0.0344(4) Uani 1 1 d . . . H33 H 0.6707 0.8596 0.2352 0.041 Uiso 1 1 calc R . . C34 C 0.6715(2) 0.96707(14) 0.17935(9) 0.0416(5) Uani 1 1 d . . . H34 H 0.5859 0.9846 0.1837 0.050 Uiso 1 1 calc R . . C35 C 0.7456(2) 1.01514(14) 0.14239(9) 0.0456(5) Uani 1 1 d . . . H35 H 0.7102 1.0646 0.1208 0.055 Uiso 1 1 calc R . . C36 C 0.8708(3) 0.99169(15) 0.13671(10) 0.0478(6) Uani 1 1 d . . . H36 H 0.9216 1.0254 0.1115 0.057 Uiso 1 1 calc R . . C37 C 0.9222(2) 0.91899(14) 0.16789(8) 0.0392(4) Uani 1 1 d . . . H37 H 1.0087 0.9035 0.1644 0.047 Uiso 1 1 calc R . . C38 C 1.11324(17) 0.70471(13) 0.16158(7) 0.0282(4) Uani 1 1 d . . . H38A H 1.1264 0.7103 0.2011 0.034 Uiso 1 1 calc R . . H38B H 1.1331 0.7679 0.1454 0.034 Uiso 1 1 calc R . . C39 C 1.20440(17) 0.63192(13) 0.13981(7) 0.0271(4) Uani 1 1 d . . . C40 C 1.26842(19) 0.56989(14) 0.17419(7) 0.0321(4) Uani 1 1 d . . . H40 H 1.2484 0.5698 0.2116 0.038 Uiso 1 1 calc R . . C41 C 1.36066(19) 0.50815(14) 0.15533(8) 0.0355(4) Uani 1 1 d . . . H41 H 1.4016 0.4654 0.1795 0.043 Uiso 1 1 calc R . . C42 C 1.39274(18) 0.50911(14) 0.10129(8) 0.0329(4) Uani 1 1 d . . . C43 C 1.32847(19) 0.56931(15) 0.06604(8) 0.0354(4) Uani 1 1 d . . . H43 H 1.3481 0.5688 0.0286 0.042 Uiso 1 1 calc R . . C44 C 1.23680(17) 0.62945(14) 0.08516(7) 0.0315(4) Uani 1 1 d . . . H44 H 1.1942 0.6705 0.0606 0.038 Uiso 1 1 calc R . . C46 C 1.5693(2) 0.40752(19) 0.11442(10) 0.0522(6) Uani 1 1 d . . . H46A H 1.6325 0.3723 0.0935 0.078 Uiso 1 1 calc R . . H46B H 1.5212 0.3622 0.1366 0.078 Uiso 1 1 calc R . . H46C H 1.6111 0.4543 0.1379 0.078 Uiso 1 1 calc R . . N9 N 0.91107(14) 0.36086(10) 0.15162(6) 0.0255(3) Uani 1 1 d . . . N20 N 0.72064(14) 0.68036(10) 0.13618(6) 0.0261(3) Uani 1 1 d . . . N21 N 0.97836(14) 0.68366(10) 0.15164(6) 0.0243(3) Uani 1 1 d . . . O19 O 0.68177(13) 0.65182(9) 0.22338(5) 0.0328(3) Uani 1 1 d . . . O22 O 0.99991(12) 0.74567(9) 0.06735(5) 0.0314(3) Uani 1 1 d . . . O25 O 0.87657(14) 0.23456(10) 0.09483(6) 0.0393(3) Uani 1 1 d . . . O26 O 1.03420(12) 0.34090(9) 0.08030(5) 0.0325(3) Uani 1 1 d . . . O45 O 1.48685(14) 0.45636(11) 0.07851(6) 0.0435(4) Uani 1 1 d . . . S31 S 0.91236(4) 0.77635(3) 0.244939(16) 0.02925(11) Uani 1 1 d . . . C101 C 0.6668(4) 0.7337(3) 0.34717(13) 0.0936(12) Uani 1 1 d . . . H10A H 0.6422 0.7354 0.3853 0.140 Uiso 1 1 calc R . . H10B H 0.5980 0.7583 0.3249 0.140 Uiso 1 1 calc R . . H10C H 0.7415 0.7736 0.3418 0.140 Uiso 1 1 calc R . . O101 O 0.6911(4) 0.6478(2) 0.33358(10) 0.1220(12) Uani 1 1 d . . . H101 H 0.7026 0.6451 0.3000 0.183 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 0.0297(9) 0.0355(10) 0.0354(10) -0.0087(8) -0.0030(8) 0.0017(8) C2 0.0369(10) 0.0335(9) 0.0373(10) -0.0034(8) -0.0094(8) 0.0102(9) C3 0.0398(11) 0.0267(9) 0.0304(9) 0.0027(7) -0.0060(8) 0.0051(8) C4 0.0293(9) 0.0234(8) 0.0225(8) -0.0005(6) -0.0028(7) 0.0006(7) C5 0.0336(9) 0.0233(8) 0.0251(8) -0.0015(7) -0.0063(7) 0.0007(7) C6 0.0364(10) 0.0278(9) 0.0312(9) -0.0041(7) -0.0010(7) -0.0004(7) C7 0.0609(13) 0.0235(8) 0.0292(9) -0.0013(7) -0.0014(9) -0.0038(9) C8 0.0316(9) 0.0223(8) 0.0256(8) 0.0041(7) -0.0065(7) -0.0031(7) C10 0.0267(9) 0.0246(8) 0.0277(8) 0.0048(7) -0.0050(7) 0.0002(7) C11 0.0338(10) 0.0234(8) 0.0354(9) 0.0030(7) -0.0080(8) -0.0037(7) C12 0.0322(10) 0.0309(9) 0.0393(10) 0.0093(8) -0.0037(8) -0.0058(8) C13 0.0338(10) 0.0365(10) 0.0356(10) 0.0083(8) 0.0024(8) -0.0033(8) C14 0.0351(10) 0.0298(9) 0.0293(9) 0.0033(7) -0.0005(7) -0.0009(7) C15 0.0301(9) 0.0225(8) 0.0279(8) 0.0036(7) -0.0044(7) -0.0013(7) C16 0.0281(9) 0.0218(8) 0.0229(8) 0.0043(6) -0.0049(7) -0.0017(7) C17 0.0365(10) 0.0245(8) 0.0220(8) 0.0011(7) -0.0033(7) -0.0056(7) C18 0.0315(9) 0.0226(8) 0.0219(8) -0.0001(6) -0.0002(7) -0.0046(7) C19 0.0332(10) 0.0194(8) 0.0250(8) -0.0029(6) 0.0000(7) -0.0029(7) C22 0.0327(9) 0.0198(8) 0.0236(8) 0.0004(6) -0.0022(7) -0.0013(7) C23 0.094(2) 0.0483(13) 0.0319(11) -0.0111(10) 0.0137(13) -0.0171(14) C24 0.0657(15) 0.0320(10) 0.0377(11) -0.0036(8) -0.0215(10) 0.0074(10) C25 0.0283(9) 0.0248(9) 0.0334(9) -0.0004(7) -0.0028(7) 0.0017(7) C27 0.0385(10) 0.0338(10) 0.0341(9) -0.0080(8) 0.0052(8) 0.0012(8) C28 0.0513(13) 0.0348(11) 0.0561(13) -0.0071(10) 0.0055(11) 0.0052(9) C29 0.0415(11) 0.0375(10) 0.0460(11) -0.0056(9) 0.0109(9) -0.0002(9) C30 0.0512(13) 0.0503(13) 0.0359(10) -0.0087(9) -0.0013(10) -0.0026(10) C32 0.0418(11) 0.0206(8) 0.0283(9) -0.0060(7) -0.0046(8) -0.0049(8) C33 0.0409(11) 0.0279(9) 0.0344(10) -0.0076(8) -0.0023(8) -0.0041(8) C34 0.0486(13) 0.0296(10) 0.0468(12) -0.0083(8) -0.0101(10) 0.0040(9) C35 0.0700(16) 0.0240(9) 0.0429(11) -0.0013(8) -0.0152(11) 0.0020(10) C36 0.0687(16) 0.0276(10) 0.0470(12) 0.0042(9) 0.0056(11) -0.0060(10) C37 0.0490(12) 0.0265(9) 0.0420(11) -0.0018(8) 0.0037(9) -0.0044(9) C38 0.0295(9) 0.0284(9) 0.0268(8) 0.0021(7) -0.0049(7) -0.0088(7) C39 0.0262(9) 0.0269(8) 0.0282(8) 0.0022(7) -0.0042(7) -0.0075(7) C40 0.0367(10) 0.0333(9) 0.0262(9) 0.0035(7) -0.0047(7) -0.0067(8) C41 0.0370(10) 0.0324(10) 0.0370(10) 0.0066(8) -0.0072(8) -0.0016(8) C42 0.0296(10) 0.0336(9) 0.0353(10) -0.0014(8) -0.0056(7) -0.0018(8) C43 0.0333(10) 0.0461(11) 0.0267(9) 0.0009(8) -0.0037(8) -0.0027(9) C44 0.0283(9) 0.0390(10) 0.0272(9) 0.0063(8) -0.0026(7) -0.0019(8) C46 0.0493(14) 0.0594(14) 0.0480(12) -0.0024(11) -0.0106(11) 0.0224(12) N9 0.0276(7) 0.0215(7) 0.0274(7) 0.0010(6) -0.0041(6) -0.0025(6) N20 0.0276(8) 0.0253(7) 0.0254(7) -0.0031(6) -0.0018(6) -0.0019(6) N21 0.0275(7) 0.0246(7) 0.0207(6) 0.0013(5) -0.0028(6) -0.0056(6) O19 0.0354(7) 0.0338(7) 0.0292(6) -0.0018(5) 0.0046(5) -0.0056(6) O22 0.0361(7) 0.0322(7) 0.0260(6) 0.0079(5) 0.0006(5) -0.0034(5) O25 0.0437(8) 0.0326(7) 0.0416(7) -0.0095(6) 0.0035(6) -0.0092(6) O26 0.0351(7) 0.0299(7) 0.0324(6) -0.0056(5) 0.0034(5) -0.0032(5) O45 0.0396(8) 0.0525(9) 0.0385(7) -0.0039(7) -0.0068(6) 0.0113(7) S31 0.0383(2) 0.0247(2) 0.0248(2) -0.00362(16) -0.00446(17) -0.00459(17) C101 0.107(3) 0.125(3) 0.0492(16) -0.0115(19) 0.0185(17) 0.023(3) O101 0.228(4) 0.0806(17) 0.0575(13) 0.0175(12) 0.039(2) 0.002(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N20 1.471(2) . ? C1 C2 1.527(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.530(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.520(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N20 1.454(2) . ? C4 C22 1.505(2) . ? C4 C5 1.567(2) . ? C5 C6 1.492(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.329(3) . ? C6 H6 0.9500 . ? C7 C24 1.493(3) . ? C7 C23 1.501(3) . ? C8 C16 1.347(3) . ? C8 N9 1.405(2) . ? C8 H8 0.9500 . ? C10 C11 1.391(2) . ? C10 N9 1.398(2) . ? C10 C15 1.402(3) . ? C11 C12 1.379(3) . ? C11 H11 0.9500 . ? C12 C13 1.388(3) . ? C12 H12 0.9500 . ? C13 C14 1.382(3) . ? C13 H13 0.9500 . ? C14 C15 1.393(3) . ? C14 H14 0.9500 . ? C15 C16 1.445(2) . ? C16 C17 1.502(2) . ? C17 C18 1.541(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 N21 1.461(2) . ? C18 C19 1.536(3) . ? C18 S31 1.8659(17) . ? C19 O19 1.231(2) . ? C19 N20 1.323(2) . ? C22 O22 1.217(2) . ? C22 N21 1.371(2) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 O25 1.205(2) . ? C25 O26 1.319(2) . ? C25 N9 1.392(2) . ? C27 O26 1.487(2) . ? C27 C29 1.506(3) . ? C27 C30 1.508(3) . ? C27 C28 1.516(3) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C32 C37 1.386(3) . ? C32 C33 1.392(3) . ? C32 S31 1.7749(19) . ? C33 C34 1.386(3) . ? C33 H33 0.9500 . ? C34 C35 1.381(3) . ? C34 H34 0.9500 . ? C35 C36 1.381(4) . ? C35 H35 0.9500 . ? C36 C37 1.385(3) . ? C36 H36 0.9500 . ? C37 H37 0.9500 . ? C38 N21 1.487(2) . ? C38 C39 1.503(3) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 C40 1.391(3) . ? C39 C44 1.396(3) . ? C40 C41 1.386(3) . ? C40 H40 0.9500 . ? C41 C42 1.380(3) . ? C41 H41 0.9500 . ? C42 O45 1.365(2) . ? C42 C43 1.390(3) . ? C43 C44 1.371(3) . ? C43 H43 0.9500 . ? C44 H44 0.9500 . ? C46 O45 1.423(3) . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C101 O101 1.268(5) . ? C101 H10A 0.9800 . ? C101 H10B 0.9800 . ? C101 H10C 0.9800 . ? O101 H101 0.8400 . ? 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 N20 C1 C2 104.05(15) . . ? N20 C1 H1A 110.9 . . ? C2 C1 H1A 110.9 . . ? N20 C1 H1B 110.9 . . ? C2 C1 H1B 110.9 . . ? H1A C1 H1B 109.0 . . ? C1 C2 C3 104.11(15) . . ? C1 C2 H2A 110.9 . . ? C3 C2 H2A 110.9 . . ? C1 C2 H2B 110.9 . . ? C3 C2 H2B 110.9 . . ? H2A C2 H2B 109.0 . . ? C4 C3 C2 102.84(15) . . ? C4 C3 H3A 111.2 . . ? C2 C3 H3A 111.2 . . ? C4 C3 H3B 111.2 . . ? C2 C3 H3B 111.2 . . ? H3A C3 H3B 109.1 . . ? N20 C4 C22 112.21(13) . . ? N20 C4 C3 102.07(14) . . ? C22 C4 C3 114.09(14) . . ? N20 C4 C5 108.14(14) . . ? C22 C4 C5 108.58(14) . . ? C3 C4 C5 111.54(14) . . ? C6 C5 C4 114.94(15) . . ? C6 C5 H5A 108.5 . . ? C4 C5 H5A 108.5 . . ? C6 C5 H5B 108.5 . . ? C4 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? C7 C6 C5 126.56(19) . . ? C7 C6 H6 116.7 . . ? C5 C6 H6 116.7 . . ? C6 C7 C24 124.9(2) . . ? C6 C7 C23 120.5(2) . . ? C24 C7 C23 114.5(2) . . ? C16 C8 N9 109.82(16) . . ? C16 C8 H8 125.1 . . ? N9 C8 H8 125.1 . . ? C11 C10 N9 130.47(17) . . ? C11 C10 C15 122.27(17) . . ? N9 C10 C15 107.23(15) . . ? C12 C11 C10 117.16(17) . . ? C12 C11 H11 121.4 . . ? C10 C11 H11 121.4 . . ? C11 C12 C13 121.26(17) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C14 C13 C12 121.67(18) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C13 C14 C15 118.16(17) . . ? C13 C14 H14 120.9 . . ? C15 C14 H14 120.9 . . ? C14 C15 C10 119.46(16) . . ? C14 C15 C16 133.01(17) . . ? C10 C15 C16 107.52(15) . . ? C8 C16 C15 107.33(15) . . ? C8 C16 C17 127.10(16) . . ? C15 C16 C17 125.56(16) . . ? C16 C17 C18 113.48(14) . . ? C16 C17 H17A 108.9 . . ? C18 C17 H17A 108.9 . . ? C16 C17 H17B 108.9 . . ? C18 C17 H17B 108.9 . . ? H17A C17 H17B 107.7 . . ? N21 C18 C19 114.51(14) . . ? N21 C18 C17 112.24(15) . . ? C19 C18 C17 110.04(14) . . ? N21 C18 S31 110.08(11) . . ? C19 C18 S31 104.14(12) . . ? C17 C18 S31 105.11(11) . . ? O19 C19 N20 121.82(17) . . ? O19 C19 C18 119.89(16) . . ? N20 C19 C18 118.09(15) . . ? O22 C22 N21 122.41(16) . . ? O22 C22 C4 120.10(15) . . ? N21 C22 C4 117.16(14) . . ? C7 C23 H23A 109.5 . . ? C7 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C7 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C7 C24 H24A 109.5 . . ? C7 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C7 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O25 C25 O26 127.73(17) . . ? O25 C25 N9 122.62(17) . . ? O26 C25 N9 109.65(15) . . ? O26 C27 C29 101.87(15) . . ? O26 C27 C30 109.48(16) . . ? C29 C27 C30 111.08(18) . . ? O26 C27 C28 109.99(17) . . ? C29 C27 C28 112.02(18) . . ? C30 C27 C28 111.93(18) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C27 C30 H30A 109.5 . . ? C27 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C27 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C37 C32 C33 119.81(19) . . ? C37 C32 S31 120.75(16) . . ? C33 C32 S31 119.39(16) . . ? C34 C33 C32 119.8(2) . . ? C34 C33 H33 120.1 . . ? C32 C33 H33 120.1 . . ? C35 C34 C33 120.0(2) . . ? C35 C34 H34 120.0 . . ? C33 C34 H34 120.0 . . ? C36 C35 C34 120.4(2) . . ? C36 C35 H35 119.8 . . ? C34 C35 H35 119.8 . . ? C35 C36 C37 119.9(2) . . ? C35 C36 H36 120.1 . . ? C37 C36 H36 120.1 . . ? C36 C37 C32 120.1(2) . . ? C36 C37 H37 119.9 . . ? C32 C37 H37 119.9 . . ? N21 C38 C39 115.63(14) . . ? N21 C38 H38A 108.4 . . ? C39 C38 H38A 108.4 . . ? N21 C38 H38B 108.4 . . ? C39 C38 H38B 108.4 . . ? H38A C38 H38B 107.4 . . ? C40 C39 C44 117.12(18) . . ? C40 C39 C38 121.07(16) . . ? C44 C39 C38 121.57(16) . . ? C41 C40 C39 121.77(18) . . ? C41 C40 H40 119.1 . . ? C39 C40 H40 119.1 . . ? C42 C41 C40 119.72(18) . . ? C42 C41 H41 120.1 . . ? C40 C41 H41 120.1 . . ? O45 C42 C41 125.24(18) . . ? O45 C42 C43 115.28(17) . . ? C41 C42 C43 119.45(19) . . ? C44 C43 C42 120.17(18) . . ? C44 C43 H43 119.9 . . ? C42 C43 H43 119.9 . . ? C43 C44 C39 121.72(17) . . ? C43 C44 H44 119.1 . . ? C39 C44 H44 119.1 . . ? O45 C46 H46A 109.5 . . ? O45 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? O45 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C25 N9 C10 125.64(15) . . ? C25 N9 C8 125.99(15) . . ? C10 N9 C8 108.08(14) . . ? C19 N20 C4 126.21(15) . . ? C19 N20 C1 122.04(15) . . ? C4 N20 C1 111.66(14) . . ? C22 N21 C18 123.46(15) . . ? C22 N21 C38 115.72(14) . . ? C18 N21 C38 117.11(13) . . ? C25 O26 C27 120.98(14) . . ? C42 O45 C46 116.92(16) . . ? C32 S31 C18 101.22(8) . . ? O101 C101 H10A 109.5 . . ? O101 C101 H10B 109.5 . . ? H10A C101 H10B 109.5 . . ? O101 C101 H10C 109.5 . . ? H10A C101 H10C 109.5 . . ? H10B C101 H10C 109.5 . . ? C101 O101 H101 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 N20 C1 C2 C3 -19.85(18) . . . . ? C1 C2 C3 C4 36.01(18) . . . . ? C2 C3 C4 N20 -37.97(17) . . . . ? C2 C3 C4 C22 -159.24(14) . . . . ? C2 C3 C4 C5 77.28(18) . . . . ? N20 C4 C5 C6 176.98(15) . . . . ? C22 C4 C5 C6 -61.03(18) . . . . ? C3 C4 C5 C6 65.5(2) . . . . ? C4 C5 C6 C7 -108.1(2) . . . . ? C5 C6 C7 C24 1.7(3) . . . . ? C5 C6 C7 C23 -179.04(19) . . . . ? N9 C10 C11 C12 179.30(17) . . . . ? C15 C10 C11 C12 1.5(3) . . . . ? C10 C11 C12 C13 -1.0(3) . . . . ? C11 C12 C13 C14 0.5(3) . . . . ? C12 C13 C14 C15 -0.4(3) . . . . ? C13 C14 C15 C10 0.8(3) . . . . ? C13 C14 C15 C16 -177.89(19) . . . . ? C11 C10 C15 C14 -1.4(3) . . . . ? N9 C10 C15 C14 -179.68(15) . . . . ? C11 C10 C15 C16 177.60(16) . . . . ? N9 C10 C15 C16 -0.67(18) . . . . ? N9 C8 C16 C15 1.01(19) . . . . ? N9 C8 C16 C17 -177.87(16) . . . . ? C14 C15 C16 C8 178.61(19) . . . . ? C10 C15 C16 C8 -0.20(19) . . . . ? C14 C15 C16 C17 -2.5(3) . . . . ? C10 C15 C16 C17 178.70(16) . . . . ? C8 C16 C17 C18 72.3(2) . . . . ? C15 C16 C17 C18 -106.35(19) . . . . ? C16 C17 C18 N21 -71.90(19) . . . . ? C16 C17 C18 C19 56.9(2) . . . . ? C16 C17 C18 S31 168.46(13) . . . . ? N21 C18 C19 O19 178.78(15) . . . . ? C17 C18 C19 O19 51.3(2) . . . . ? S31 C18 C19 O19 -60.96(18) . . . . ? N21 C18 C19 N20 -6.2(2) . . . . ? C17 C18 C19 N20 -133.68(16) . . . . ? S31 C18 C19 N20 114.11(14) . . . . ? N20 C4 C22 O22 -154.72(16) . . . . ? C3 C4 C22 O22 -39.3(2) . . . . ? C5 C4 C22 O22 85.82(19) . . . . ? N20 C4 C22 N21 31.7(2) . . . . ? C3 C4 C22 N21 147.17(16) . . . . ? C5 C4 C22 N21 -87.76(17) . . . . ? C37 C32 C33 C34 0.7(3) . . . . ? S31 C32 C33 C34 178.39(14) . . . . ? C32 C33 C34 C35 0.8(3) . . . . ? C33 C34 C35 C36 -1.5(3) . . . . ? C34 C35 C36 C37 0.6(3) . . . . ? C35 C36 C37 C32 1.0(3) . . . . ? C33 C32 C37 C36 -1.7(3) . . . . ? S31 C32 C37 C36 -179.29(16) . . . . ? N21 C38 C39 C40 -107.30(19) . . . . ? N21 C38 C39 C44 78.6(2) . . . . ? C44 C39 C40 C41 0.1(3) . . . . ? C38 C39 C40 C41 -174.30(17) . . . . ? C39 C40 C41 C42 1.5(3) . . . . ? C40 C41 C42 O45 175.74(18) . . . . ? C40 C41 C42 C43 -2.6(3) . . . . ? O45 C42 C43 C44 -176.39(18) . . . . ? C41 C42 C43 C44 2.1(3) . . . . ? C42 C43 C44 C39 -0.5(3) . . . . ? C40 C39 C44 C43 -0.6(3) . . . . ? C38 C39 C44 C43 173.76(17) . . . . ? O25 C25 N9 C10 0.2(3) . . . . ? O26 C25 N9 C10 179.81(15) . . . . ? O25 C25 N9 C8 -172.97(17) . . . . ? O26 C25 N9 C8 6.7(2) . . . . ? C11 C10 N9 C25 9.0(3) . . . . ? C15 C10 N9 C25 -172.88(16) . . . . ? C11 C10 N9 C8 -176.80(18) . . . . ? C15 C10 N9 C8 1.28(18) . . . . ? C16 C8 N9 C25 172.68(16) . . . . ? C16 C8 N9 C10 -1.45(19) . . . . ? O19 C19 N20 C4 -170.02(15) . . . . ? C18 C19 N20 C4 15.0(2) . . . . ? O19 C19 N20 C1 13.6(3) . . . . ? C18 C19 N20 C1 -161.38(15) . . . . ? C22 C4 N20 C19 -27.3(2) . . . . ? C3 C4 N20 C19 -149.82(17) . . . . ? C5 C4 N20 C19 92.47(19) . . . . ? C22 C4 N20 C1 149.46(14) . . . . ? C3 C4 N20 C1 26.90(18) . . . . ? C5 C4 N20 C1 -90.81(16) . . . . ? C2 C1 N20 C19 172.40(16) . . . . ? C2 C1 N20 C4 -4.48(19) . . . . ? O22 C22 N21 C18 159.07(16) . . . . ? C4 C22 N21 C18 -27.5(2) . . . . ? O22 C22 N21 C38 1.4(2) . . . . ? C4 C22 N21 C38 174.86(14) . . . . ? C19 C18 N21 C22 13.7(2) . . . . ? C17 C18 N21 C22 140.11(16) . . . . ? S31 C18 N21 C22 -103.20(16) . . . . ? C19 C18 N21 C38 171.06(15) . . . . ? C17 C18 N21 C38 -62.55(19) . . . . ? S31 C18 N21 C38 54.15(17) . . . . ? C39 C38 N21 C22 -82.39(19) . . . . ? C39 C38 N21 C18 118.51(16) . . . . ? O25 C25 O26 C27 3.2(3) . . . . ? N9 C25 O26 C27 -176.39(15) . . . . ? C29 C27 O26 C25 -179.94(16) . . . . ? C30 C27 O26 C25 62.4(2) . . . . ? C28 C27 O26 C25 -61.0(2) . . . . ? C41 C42 O45 C46 -9.6(3) . . . . ? C43 C42 O45 C46 168.9(2) . . . . ? C37 C32 S31 C18 -86.60(16) . . . . ? C33 C32 S31 C18 95.77(15) . . . . ? N21 C18 S31 C32 65.09(14) . . . . ? C19 C18 S31 C32 -58.12(13) . . . . ? C17 C18 S31 C32 -173.85(12) . . . . ? 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 O101 H101 O19 0.84 1.91 2.729(3) 164.0 . _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 68.22 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.728 _refine_diff_density_min -0.547 _refine_diff_density_rms 0.040 _database_code_depnum_ccdc_archive 'CCDC 936852'