# Article Ref. B107691B - Perkin Transactions 2 # Title: (alphaMe)Hyv: chemo-enzymatic synthesis, # and preparation and preferred conformation of model depsipeptides # Authors: C. Peggion, A. Barazza, F. Formaggio, M. Crisma, C. Toniolo, M. Villa, # C. Tomasini, H. Mayrhofer, P. Pöchlauer, B. Kaptein and Q.B. Broxterman data_ctf86 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common H-L-(\aMe)Hyv-L-Val-OMe _chemical_melting_point 345-347 _chemical_formula_moiety ? _chemical_formula_sum 'C12 H23 N O4' _chemical_formula_weight 245.31 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 Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.900(2) _cell_length_b 10.151(3) _cell_length_c 12.088(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.64(3) _cell_angle_gamma 90.00 _cell_volume 711.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 48 _cell_measurement_theta_min 12 _cell_measurement_theta_max 24 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.145 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.698 _exptl_absorpt_correction_type 'not carried out' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Philips PW1100 diffractometer' _diffrn_measurement_method '\q-2\q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 1179 _diffrn_reflns_av_R_equivalents 0.0138 _diffrn_reflns_av_sigmaI/netI 0.0069 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.72 _diffrn_reflns_theta_max 60.01 _reflns_number_total 1126 _reflns_number_gt 1095 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material ? _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 fullcycle _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0848P)^2^+0.0735P] 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 SHELXL _refine_ls_extinction_coef 0.025(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(4) _refine_ls_number_reflns 1126 _refine_ls_number_parameters 155 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1158 _refine_ls_wR_factor_gt 0.1149 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0.311 _refine_ls_shift/su_mean 0.073 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 O01 O 0.7098(3) 0.8867(2) 0.75309(14) 0.0542(6) Uani 1 1 d . . . H01 H 0.8452 0.8759 0.7825 0.081 Uiso 1 1 calc R . . C1A C 0.5729(4) 0.8991(3) 0.8386(2) 0.0460(6) Uani 1 1 d . . . C1B1 C 0.5393(5) 1.0452(3) 0.8645(2) 0.0549(7) Uani 1 1 d . . . H1B1 H 0.4448 1.0487 0.9231 0.066 Uiso 1 1 calc R . . C1G1 C 0.7668(6) 1.1124(4) 0.9114(3) 0.0717(9) Uani 1 1 d . . . H1G1 H 0.8643 1.1105 0.8560 0.108 Uiso 1 1 calc R . . H1G2 H 0.8414 1.0669 0.9778 0.108 Uiso 1 1 calc R . . H1G3 H 0.7385 1.2021 0.9299 0.108 Uiso 1 1 calc R . . C1G2 C 0.4101(7) 1.1197(4) 0.7636(4) 0.0819(11) Uani 1 1 d . . . H1G4 H 0.4986 1.1189 0.7045 0.123 Uiso 1 1 calc R . . H1G5 H 0.3864 1.2091 0.7848 0.123 Uiso 1 1 calc R . . H1G6 H 0.2636 1.0784 0.7376 0.123 Uiso 1 1 calc R . . C1B2 C 0.6761(5) 0.8197(4) 0.9422(2) 0.0612(8) Uani 1 1 d . . . H1B2 H 0.6809 0.7283 0.9224 0.092 Uiso 1 1 calc R . . H1B3 H 0.5829 0.8303 0.9988 0.092 Uiso 1 1 calc R . . H1B4 H 0.8297 0.8503 0.9708 0.092 Uiso 1 1 calc R . . C1 C 0.3385(4) 0.8369(3) 0.7913(2) 0.0475(7) Uani 1 1 d . . . O1 O 0.1742(3) 0.8509(3) 0.83974(17) 0.0674(7) Uani 1 1 d . . . N2 N 0.3270(3) 0.7634(3) 0.69939(19) 0.0546(6) Uani 1 1 d . . . H2 H 0.4442 0.7600 0.6664 0.066 Uiso 1 1 calc R . . C2A C 0.1214(4) 0.6890(3) 0.6535(2) 0.0538(7) Uani 1 1 d . . . H2A H -0.0107 0.7491 0.6453 0.065 Uiso 1 1 calc R . . C2B C 0.1325(5) 0.6322(4) 0.5364(2) 0.0605(8) Uani 1 1 d . . . H2B H -0.0102 0.5823 0.5123 0.073 Uiso 1 1 calc R . . C2G1 C 0.3303(7) 0.5365(5) 0.5365(3) 0.0823(11) Uani 1 1 d . . . H2G1 H 0.3216 0.5006 0.4623 0.124 Uiso 1 1 calc R . . H2G2 H 0.3201 0.4664 0.5886 0.124 Uiso 1 1 calc R . . H2G3 H 0.4743 0.5819 0.5585 0.124 Uiso 1 1 calc R . . C2G2 C 0.1337(8) 0.7404(5) 0.4517(3) 0.0947(13) Uani 1 1 d . . . H2G4 H 0.2773 0.7872 0.4685 0.142 Uiso 1 1 calc R . . H2G5 H 0.0088 0.8000 0.4548 0.142 Uiso 1 1 calc R . . H2G6 H 0.1159 0.7030 0.3776 0.142 Uiso 1 1 calc R . . C2 C 0.0839(4) 0.5807(3) 0.7349(2) 0.0537(7) Uani 1 1 d . . . O2 O 0.2305(4) 0.5245(3) 0.7975(2) 0.0852(8) Uani 1 1 d . . . OT O -0.1402(3) 0.5552(3) 0.72502(18) 0.0681(6) Uani 1 1 d . . . CT C -0.2003(6) 0.4526(4) 0.7980(3) 0.0794(11) Uani 1 1 d . . . HT1 H -0.1357 0.3704 0.7798 0.119 Uiso 1 1 calc R . . HT2 H -0.3650 0.4449 0.7874 0.119 Uiso 1 1 calc R . . HT3 H -0.1399 0.4748 0.8750 0.119 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 O01 0.0357(9) 0.0739(13) 0.0553(10) -0.0092(10) 0.0148(7) -0.0053(9) C1A 0.0337(12) 0.0588(16) 0.0465(12) -0.0038(13) 0.0100(10) -0.0043(12) C1B1 0.0493(14) 0.0618(16) 0.0567(15) -0.0048(14) 0.0177(12) -0.0028(13) C1G1 0.071(2) 0.0638(19) 0.079(2) -0.0118(18) 0.0120(17) -0.0155(17) C1G2 0.076(2) 0.068(2) 0.100(3) 0.013(2) 0.011(2) 0.0136(19) C1B2 0.0500(15) 0.0701(19) 0.0615(17) 0.0067(16) 0.0051(13) -0.0045(14) C1 0.0346(12) 0.0570(16) 0.0510(13) -0.0052(12) 0.0080(11) -0.0016(12) O1 0.0354(10) 0.0987(18) 0.0703(12) -0.0187(12) 0.0157(8) -0.0072(11) N2 0.0397(11) 0.0683(16) 0.0570(12) -0.0126(13) 0.0120(9) -0.0083(12) C2A 0.0397(14) 0.0618(17) 0.0579(15) -0.0070(14) 0.0040(11) -0.0059(13) C2B 0.0545(16) 0.0684(18) 0.0546(16) -0.0047(14) -0.0003(13) -0.0096(14) C2G1 0.083(2) 0.095(3) 0.0686(18) -0.018(2) 0.0145(16) 0.002(2) C2G2 0.112(3) 0.105(3) 0.064(2) 0.009(2) 0.006(2) -0.014(3) C2 0.0407(13) 0.0652(18) 0.0538(14) -0.0073(14) 0.0050(11) -0.0046(13) O2 0.0535(12) 0.115(2) 0.0847(15) 0.0300(16) 0.0068(11) 0.0081(14) OT 0.0458(11) 0.0753(15) 0.0803(13) 0.0085(12) 0.0044(9) -0.0133(11) CT 0.066(2) 0.081(2) 0.091(2) 0.008(2) 0.0152(17) -0.0197(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O01 C1A 1.430(3) . ? C1A C1B2 1.519(4) . ? C1A C1 1.531(3) . ? C1A C1B1 1.536(4) . ? C1B1 C1G2 1.516(5) . ? C1B1 C1G1 1.519(4) . ? C1 O1 1.230(3) . ? C1 N2 1.329(4) . ? N2 C2A 1.450(3) . ? C2A C2 1.518(4) . ? C2A C2B 1.540(4) . ? C2B C2G2 1.502(5) . ? C2B C2G1 1.519(5) . ? C2 O2 1.185(4) . ? C2 OT 1.330(3) . ? OT CT 1.450(4) . ? 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 O01 C1A C1B2 110.8(2) . . ? O01 C1A C1 106.56(19) . . ? C1B2 C1A C1 106.6(2) . . ? O01 C1A C1B1 110.1(2) . . ? C1B2 C1A C1B1 113.1(2) . . ? C1 C1A C1B1 109.4(2) . . ? C1G2 C1B1 C1G1 110.7(3) . . ? C1G2 C1B1 C1A 112.5(3) . . ? C1G1 C1B1 C1A 111.8(2) . . ? O1 C1 N2 122.6(2) . . ? O1 C1 C1A 120.8(2) . . ? N2 C1 C1A 116.5(2) . . ? C1 N2 C2A 121.5(2) . . ? N2 C2A C2 109.9(2) . . ? N2 C2A C2B 111.8(2) . . ? C2 C2A C2B 111.2(2) . . ? C2G2 C2B C2G1 111.6(3) . . ? C2G2 C2B C2A 111.1(3) . . ? C2G1 C2B C2A 113.7(3) . . ? O2 C2 OT 124.0(3) . . ? O2 C2 C2A 125.9(3) . . ? OT C2 C2A 110.1(2) . . ? C2 OT CT 115.8(3) . . ? 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 O01 C1A C1B1 C1G2 62.4(3) . . . . y C1B2 C1A C1B1 C1G2 -173.1(3) . . . . ? C1 C1A C1B1 C1G2 -54.4(3) . . . . ? O01 C1A C1B1 C1G1 -62.9(3) . . . . y C1B2 C1A C1B1 C1G1 61.6(3) . . . . ? C1 C1A C1B1 C1G1 -179.7(2) . . . . ? O01 C1A C1 O1 -169.0(3) . . . . ? C1B2 C1A C1 O1 72.6(3) . . . . ? C1B1 C1A C1 O1 -50.0(3) . . . . ? O01 C1A C1 N2 13.9(3) . . . . y C1B2 C1A C1 N2 -104.4(3) . . . . ? C1B1 C1A C1 N2 133.0(3) . . . . ? O1 C1 N2 C2A -3.2(4) . . . . ? C1A C1 N2 C2A 173.7(2) . . . . y C1 N2 C2A C2 -66.3(4) . . . . y C1 N2 C2A C2B 169.7(3) . . . . ? N2 C2A C2B C2G2 -65.3(4) . . . . y C2 C2A C2B C2G2 171.5(3) . . . . ? N2 C2A C2B C2G1 61.6(4) . . . . ? C2 C2A C2B C2G1 -61.7(3) . . . . y N2 C2A C2 O2 -31.0(4) . . . . ? C2B C2A C2 O2 93.4(4) . . . . ? N2 C2A C2 OT 150.2(2) . . . . y C2B C2A C2 OT -85.5(3) . . . . ? O2 C2 OT CT 0.8(5) . . . . ? C2A C2 OT CT 179.7(3) . . . . y 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 O01 H01 O1 0.82 1.95 2.771(3) 175.1 1_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 60.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.189 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.046 #===END=== data_ctf89b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Ac-L-(\aMe)Hyv-L-Val-OMe _chemical_melting_point 329-331 _chemical_formula_moiety ? _chemical_formula_sum 'C14 H25 N O5' _chemical_formula_weight 287.35 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 Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.287(3) _cell_length_b 17.451(4) _cell_length_c 13.315(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.59(8) _cell_angle_gamma 90.00 _cell_volume 2526.2(11) _cell_formula_units_Z 6 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 48 _cell_measurement_theta_min 12 _cell_measurement_theta_max 20 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.133 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.705 _exptl_absorpt_correction_type 'not carried out' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Philips PW1100 diffractometer' _diffrn_measurement_method '\q-2\q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% negligible _diffrn_reflns_number 4335 _diffrn_reflns_av_R_equivalents 0.0680 _diffrn_reflns_av_sigmaI/netI 0.0154 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 60.02 _reflns_number_total 4158 _reflns_number_gt 3746 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material ? _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 fullcycle _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1554P)^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 constrained _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0115(13) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(3) _refine_ls_number_reflns 4158 _refine_ls_number_parameters 542 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.0676 _refine_ls_R_factor_gt 0.0641 _refine_ls_wR_factor_ref 0.1760 _refine_ls_wR_factor_gt 0.1711 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.249 _refine_ls_shift/su_mean 0.069 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 C01A C 0.4752(5) -0.3587(3) 0.4430(4) 0.1048(15) Uani 1 1 d . . . H01A H 0.4885 -0.3183 0.3983 0.157 Uiso 1 1 calc R . . H01B H 0.5485 -0.3889 0.4657 0.157 Uiso 1 1 calc R . . H01C H 0.4550 -0.3369 0.5025 0.157 Uiso 1 1 calc R . . C0A C 0.3724(4) -0.4079(3) 0.3850(3) 0.0837(11) Uani 1 1 d . . . O0A O 0.2880(4) -0.3878(2) 0.3142(3) 0.1134(11) Uani 1 1 d . . . O01 O 0.3836(2) -0.47943(14) 0.42514(17) 0.0678(6) Uani 1 1 d . . . C1A C 0.2845(3) -0.5341(2) 0.3847(2) 0.0642(8) Uani 1 1 d D . . C1B1 C 0.3176(3) -0.6019(2) 0.4613(3) 0.0690(9) Uani 1 1 d D . . H1B1 H 0.3250 -0.5810 0.5310 0.083 Uiso 1 1 calc R . . C1G1 C 0.4427(4) -0.6375(3) 0.4639(4) 0.0939(12) Uani 1 1 d D . . H1G1 H 0.4635 -0.6754 0.5182 0.141 Uiso 1 1 calc R . . H1G2 H 0.5045 -0.5983 0.4773 0.141 Uiso 1 1 calc R . . H1G3 H 0.4383 -0.6613 0.3980 0.141 Uiso 1 1 calc R . . C1G2 C 0.2196(5) -0.6631(3) 0.4433(4) 0.0994(13) Uani 1 1 d D . . H1G4 H 0.2108 -0.6863 0.3763 0.149 Uiso 1 1 calc R . . H1G5 H 0.1428 -0.6405 0.4455 0.149 Uiso 1 1 calc R . . H1G6 H 0.2429 -0.7015 0.4966 0.149 Uiso 1 1 calc R . . C1B2 C 0.2778(4) -0.5562(3) 0.2726(3) 0.0810(10) Uani 1 1 d . . . H1B2 H 0.2366 -0.5165 0.2264 0.122 Uiso 1 1 calc R . . H1B3 H 0.2330 -0.6033 0.2555 0.122 Uiso 1 1 calc R . . H1B4 H 0.3595 -0.5627 0.2652 0.122 Uiso 1 1 calc R . . C1 C 0.1625(3) -0.4989(2) 0.3931(2) 0.0624(8) Uani 1 1 d . . . O1 O 0.0673(2) -0.50899(18) 0.32479(16) 0.0783(7) Uani 1 1 d . . . N2 N 0.1663(2) -0.46346(17) 0.48188(19) 0.0629(7) Uani 1 1 d . . . H2 H 0.2356 -0.4605 0.5286 0.076 Uiso 1 1 calc R . . C2A C 0.0589(3) -0.4295(2) 0.5035(2) 0.0710(9) Uani 1 1 d D . . H2A H -0.0134 -0.4569 0.4616 0.085 Uiso 1 1 calc R . . C2B C 0.0609(3) -0.4392(3) 0.6181(3) 0.0800(10) Uani 1 1 d D . . H2B H 0.1345 -0.4137 0.6612 0.096 Uiso 1 1 calc R . . C2G1 C -0.0516(4) -0.4025(4) 0.6401(3) 0.1015(15) Uani 1 1 d D . . H2G1 H -0.1242 -0.4296 0.6030 0.152 Uiso 1 1 calc R . . H2G2 H -0.0575 -0.3500 0.6178 0.152 Uiso 1 1 calc R . . H2G3 H -0.0444 -0.4046 0.7136 0.152 Uiso 1 1 calc R . . C2G2 C 0.0673(6) -0.5226(4) 0.6462(4) 0.1184(18) Uani 1 1 d D . . H2G4 H 0.0710 -0.5280 0.7188 0.178 Uiso 1 1 calc R . . H2G5 H 0.1394 -0.5449 0.6331 0.178 Uiso 1 1 calc R . . H2G6 H -0.0046 -0.5483 0.6049 0.178 Uiso 1 1 calc R . . C2 C 0.0457(4) -0.3469(3) 0.4710(3) 0.0885(12) Uani 1 1 d . . . O2 O -0.0505(4) -0.3178(3) 0.4265(3) 0.1376(16) Uani 1 1 d . . . OTA O 0.1508(4) -0.30944(19) 0.4994(3) 0.1137(11) Uani 1 1 d . . . CTA C 0.1529(10) -0.2292(4) 0.4703(8) 0.171(3) Uani 1 1 d . . . HTA1 H 0.1520 -0.2256 0.3982 0.256 Uiso 1 1 calc R . . HTA2 H 0.2260 -0.2054 0.5125 0.256 Uiso 1 1 calc R . . HTA3 H 0.0819 -0.2037 0.4810 0.256 Uiso 1 1 calc R . . C01B C -0.0742(5) -0.7182(4) 0.2165(4) 0.1163(18) Uani 1 1 d . . . H01D H -0.1179 -0.7609 0.2348 0.174 Uiso 1 1 calc R . . H01E H -0.0219 -0.6960 0.2787 0.174 Uiso 1 1 calc R . . H01F H -0.0250 -0.7355 0.1723 0.174 Uiso 1 1 calc R . . C0B C -0.1628(4) -0.6603(3) 0.1609(3) 0.0900(12) Uani 1 1 d . . . O0B O -0.2100(4) -0.6593(2) 0.0700(2) 0.1221(13) Uani 1 1 d . . . O03 O -0.1866(2) -0.60834(15) 0.22720(18) 0.0742(6) Uani 1 1 d . . . C3A C -0.2753(3) -0.5468(2) 0.1887(2) 0.0648(8) Uani 1 1 d D . . C3B1 C -0.2592(3) -0.4934(2) 0.2830(3) 0.0753(10) Uani 1 1 d D . . H3B1 H -0.1723 -0.4784 0.3041 0.090 Uiso 1 1 calc R . . C3G1 C -0.3328(5) -0.4204(3) 0.2574(4) 0.1000(13) Uani 1 1 d D . . H3G1 H -0.4189 -0.4320 0.2428 0.150 Uiso 1 1 calc R . . H3G2 H -0.3164 -0.3967 0.1975 0.150 Uiso 1 1 calc R . . H3G3 H -0.3099 -0.3860 0.3157 0.150 Uiso 1 1 calc R . . C3G2 C -0.2850(5) -0.5334(4) 0.3764(3) 0.1103(16) Uani 1 1 d D . . H3G4 H -0.2644 -0.4997 0.4355 0.165 Uiso 1 1 calc R . . H3G5 H -0.2362 -0.5791 0.3919 0.165 Uiso 1 1 calc R . . H3G6 H -0.3706 -0.5465 0.3606 0.165 Uiso 1 1 calc R . . C3B2 C -0.4047(4) -0.5792(3) 0.1500(4) 0.0877(12) Uani 1 1 d . . . H3B2 H -0.4093 -0.6119 0.0910 0.132 Uiso 1 1 calc R . . H3B3 H -0.4625 -0.5379 0.1298 0.132 Uiso 1 1 calc R . . H3B4 H -0.4241 -0.6083 0.2047 0.132 Uiso 1 1 calc R . . C3 C -0.2385(3) -0.5028(2) 0.1012(2) 0.0632(8) Uani 1 1 d . . . O3 O -0.3162(2) -0.48242(17) 0.02416(17) 0.0773(7) Uani 1 1 d . . . N4 N -0.1202(2) -0.4852(2) 0.11987(19) 0.0689(8) Uani 1 1 d . . . H4 H -0.0696 -0.5006 0.1768 0.083 Uiso 1 1 calc R . . C4A C -0.0741(3) -0.4403(3) 0.0457(3) 0.0816(11) Uani 1 1 d D . . H4A H -0.1452 -0.4143 -0.0003 0.098 Uiso 1 1 calc R . . C4B C 0.0162(3) -0.3782(3) 0.0978(3) 0.0862(12) Uani 1 1 d D . . H4B H 0.0909 -0.4024 0.1410 0.103 Uiso 1 1 calc R . . C4G1 C 0.0503(5) -0.3276(4) 0.0161(5) 0.126(2) Uani 1 1 d D . . H4G1 H 0.0764 -0.3593 -0.0329 0.188 Uiso 1 1 calc R . . H4G2 H 0.1159 -0.2937 0.0498 0.188 Uiso 1 1 calc R . . H4G3 H -0.0200 -0.2980 -0.0200 0.188 Uiso 1 1 calc R . . C4G2 C -0.0394(6) -0.3274(4) 0.1668(6) 0.134(2) Uani 1 1 d D . . H4G4 H -0.1143 -0.3048 0.1254 0.201 Uiso 1 1 calc R . . H4G5 H 0.0178 -0.2876 0.1970 0.201 Uiso 1 1 calc R . . H4G6 H -0.0568 -0.3578 0.2212 0.201 Uiso 1 1 calc R . . C4 C -0.0193(4) -0.4889(4) -0.0217(3) 0.0945(14) Uani 1 1 d . . . O4 O -0.0433(4) -0.4830(4) -0.1135(2) 0.1501(19) Uani 1 1 d . . . OTB O 0.0576(4) -0.5381(3) 0.0331(3) 0.1222(13) Uani 1 1 d . . . CTB C 0.1209(10) -0.5877(7) -0.0256(6) 0.184(4) Uani 1 1 d . . . HTB1 H 0.0617 -0.6197 -0.0723 0.276 Uiso 1 1 calc R . . HTB2 H 0.1797 -0.6193 0.0222 0.276 Uiso 1 1 calc R . . HTB3 H 0.1624 -0.5566 -0.0649 0.276 Uiso 1 1 calc R . . C01C C -0.6380(5) -0.3963(7) 0.0360(4) 0.154(3) Uani 1 1 d . . . H01G H -0.7000 -0.3638 0.0505 0.231 Uiso 1 1 calc R . . H01H H -0.5585 -0.3808 0.0780 0.231 Uiso 1 1 calc R . . H01I H -0.6532 -0.4484 0.0520 0.231 Uiso 1 1 calc R . . C0C C -0.6417(4) -0.3902(3) -0.0751(3) 0.0964(14) Uani 1 1 d . . . O0C O -0.7264(3) -0.4084(3) -0.1458(2) 0.1170(13) Uani 1 1 d . . . O05 O -0.5352(2) -0.36308(17) -0.0879(2) 0.0872(8) Uani 1 1 d . . . C5A C -0.5212(3) -0.3576(2) -0.1921(3) 0.0802(10) Uani 1 1 d D . . C5B1 C -0.3824(3) -0.3349(2) -0.1708(4) 0.0932(13) Uani 1 1 d D . . H5B1 H -0.3362 -0.3740 -0.1232 0.112 Uiso 1 1 calc R . . C5G1 C -0.3525(5) -0.2590(3) -0.1134(6) 0.137(2) Uani 1 1 d D . . H5G1 H -0.3924 -0.2181 -0.1580 0.205 Uiso 1 1 calc R . . H5G2 H -0.2651 -0.2510 -0.0943 0.205 Uiso 1 1 calc R . . H5G3 H -0.3811 -0.2600 -0.0517 0.205 Uiso 1 1 calc R . . C5G2 C -0.3384(5) -0.3399(4) -0.2678(5) 0.127(2) Uani 1 1 d D . . H5G4 H -0.3872 -0.3067 -0.3204 0.190 Uiso 1 1 calc R . . H5G5 H -0.3462 -0.3917 -0.2930 0.190 Uiso 1 1 calc R . . H5G6 H -0.2537 -0.3245 -0.2520 0.190 Uiso 1 1 calc R . . C5B2 C -0.6042(4) -0.2970(3) -0.2564(4) 0.1024(15) Uani 1 1 d . . . H5B2 H -0.6874 -0.3154 -0.2764 0.154 Uiso 1 1 calc R . . H5B3 H -0.5779 -0.2860 -0.3177 0.154 Uiso 1 1 calc R . . H5B4 H -0.6000 -0.2512 -0.2157 0.154 Uiso 1 1 calc R . . C5 C -0.5439(3) -0.4359(2) -0.2463(2) 0.0615(8) Uani 1 1 d . . . O5 O -0.6016(2) -0.44181(17) -0.33631(18) 0.0837(8) Uani 1 1 d . . . N6 N -0.4859(2) -0.49385(16) -0.1895(2) 0.0636(7) Uani 1 1 d . . . H6 H -0.4401 -0.4847 -0.1278 0.076 Uiso 1 1 calc R . . C6A C -0.4971(3) -0.5726(2) -0.2279(3) 0.0725(9) Uani 1 1 d D . . H6A H -0.5211 -0.5715 -0.3043 0.087 Uiso 1 1 calc R . . C6B C -0.3705(5) -0.6132(3) -0.1900(5) 0.1101(17) Uani 1 1 d D . . H6B H -0.3387 -0.6056 -0.1146 0.132 Uiso 1 1 calc R . . C6G1 C -0.2803(6) -0.5792(6) -0.2436(8) 0.171(4) Uani 1 1 d D . . H6G1 H -0.3236 -0.5627 -0.3125 0.257 Uiso 1 1 calc R . . H6G2 H -0.2204 -0.6171 -0.2482 0.257 Uiso 1 1 calc R . . H6G3 H -0.2396 -0.5361 -0.2042 0.257 Uiso 1 1 calc R . . C6G2 C -0.3843(9) -0.7002(4) -0.2126(8) 0.171(4) Uani 1 1 d D . . H6G4 H -0.4338 -0.7082 -0.2826 0.256 Uiso 1 1 calc R . . H6G5 H -0.4231 -0.7239 -0.1646 0.256 Uiso 1 1 calc R . . H6G6 H -0.3045 -0.7225 -0.2046 0.256 Uiso 1 1 calc R . . C6 C -0.5960(4) -0.6136(2) -0.1915(3) 0.0813(10) Uani 1 1 d . . . O6 O -0.6116(4) -0.6099(3) -0.1090(3) 0.1227(13) Uani 1 1 d . . . OTC O -0.6629(3) -0.65665(17) -0.2697(2) 0.0961(9) Uani 1 1 d . . . CTC C -0.7580(6) -0.7027(4) -0.2418(5) 0.130(2) Uani 1 1 d . . . HTC1 H -0.7205 -0.7354 -0.1841 0.195 Uiso 1 1 calc R . . HTC2 H -0.7999 -0.7334 -0.3005 0.195 Uiso 1 1 calc R . . HTC3 H -0.8160 -0.6693 -0.2226 0.195 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 C01A 0.116(3) 0.076(3) 0.129(4) -0.012(3) 0.045(3) -0.028(3) C0A 0.090(3) 0.071(3) 0.098(3) 0.005(2) 0.038(2) -0.005(2) O0A 0.128(3) 0.082(2) 0.119(2) 0.031(2) 0.013(2) 0.001(2) O01 0.0638(13) 0.0632(14) 0.0773(13) -0.0027(12) 0.0203(10) 0.0013(11) C1A 0.0627(17) 0.065(2) 0.0628(16) -0.0033(15) 0.0124(14) 0.0011(16) C1B1 0.0685(19) 0.0600(19) 0.075(2) 0.0004(17) 0.0138(15) 0.0051(16) C1G1 0.088(3) 0.074(3) 0.117(3) 0.001(2) 0.025(2) 0.021(2) C1G2 0.112(3) 0.071(3) 0.109(3) 0.000(2) 0.020(3) -0.010(2) C1B2 0.081(2) 0.092(3) 0.073(2) -0.009(2) 0.0277(18) 0.009(2) C1 0.0609(17) 0.070(2) 0.0542(16) 0.0059(15) 0.0110(13) 0.0022(15) O1 0.0602(13) 0.105(2) 0.0611(12) -0.0103(13) 0.0009(10) 0.0058(13) N2 0.0528(13) 0.0738(18) 0.0576(14) -0.0044(13) 0.0070(10) 0.0063(12) C2A 0.0598(17) 0.083(2) 0.0643(17) -0.0083(18) 0.0070(14) 0.0112(18) C2B 0.073(2) 0.096(3) 0.069(2) -0.007(2) 0.0155(16) 0.009(2) C2G1 0.099(3) 0.122(4) 0.092(3) -0.018(3) 0.042(2) 0.006(3) C2G2 0.145(4) 0.116(4) 0.108(3) 0.023(3) 0.058(3) 0.021(4) C2 0.094(3) 0.097(3) 0.071(2) 0.004(2) 0.0170(19) 0.036(3) O2 0.122(3) 0.149(4) 0.136(3) 0.042(3) 0.024(2) 0.075(3) OTA 0.133(3) 0.0679(19) 0.130(2) 0.0081(18) 0.017(2) 0.0159(19) CTA 0.209(8) 0.075(4) 0.229(9) 0.018(5) 0.059(7) 0.001(5) C01B 0.117(4) 0.099(4) 0.118(4) 0.005(3) 0.007(3) 0.031(3) C0B 0.097(3) 0.078(3) 0.085(2) -0.003(2) 0.007(2) 0.014(2) O0B 0.151(3) 0.105(3) 0.090(2) -0.0207(19) -0.002(2) 0.036(2) O03 0.0776(14) 0.0650(14) 0.0747(14) 0.0079(12) 0.0112(11) 0.0038(12) C3A 0.0595(16) 0.063(2) 0.0688(18) 0.0017(15) 0.0117(14) -0.0011(15) C3B1 0.0666(19) 0.088(3) 0.075(2) -0.007(2) 0.0249(16) -0.0102(19) C3G1 0.108(3) 0.088(3) 0.111(3) -0.014(3) 0.041(3) 0.009(3) C3G2 0.123(4) 0.128(4) 0.092(3) 0.000(3) 0.051(3) -0.012(4) C3B2 0.072(2) 0.078(3) 0.107(3) 0.002(2) 0.014(2) -0.016(2) C3 0.0581(18) 0.064(2) 0.0629(17) -0.0030(15) 0.0082(14) 0.0022(15) O3 0.0655(13) 0.0821(17) 0.0719(13) 0.0058(13) -0.0025(11) -0.0037(13) N4 0.0529(14) 0.093(2) 0.0564(13) 0.0107(15) 0.0077(11) 0.0034(14) C4A 0.0649(19) 0.114(3) 0.0634(18) 0.017(2) 0.0133(15) -0.004(2) C4B 0.070(2) 0.092(3) 0.100(3) 0.018(2) 0.030(2) 0.000(2) C4G1 0.110(3) 0.111(4) 0.165(5) 0.045(4) 0.052(3) -0.005(3) C4G2 0.153(5) 0.098(4) 0.171(5) -0.003(4) 0.080(4) 0.003(4) C4 0.091(3) 0.134(4) 0.062(2) 0.000(3) 0.0274(19) -0.020(3) O4 0.160(3) 0.220(6) 0.0765(19) 0.000(3) 0.042(2) -0.016(4) OTB 0.146(3) 0.133(3) 0.0863(19) -0.007(2) 0.0291(19) 0.044(3) CTB 0.212(9) 0.196(10) 0.150(6) -0.053(6) 0.058(6) 0.054(8) C01C 0.114(4) 0.246(10) 0.103(3) -0.018(5) 0.029(3) 0.041(6) C0C 0.076(2) 0.115(4) 0.094(3) -0.010(3) 0.018(2) 0.022(3) O0C 0.0739(17) 0.166(4) 0.104(2) -0.018(2) 0.0119(16) -0.011(2) O05 0.0770(16) 0.0792(18) 0.0945(17) -0.0198(14) 0.0043(13) 0.0128(14) C5A 0.075(2) 0.056(2) 0.096(3) -0.0030(19) -0.0017(19) 0.0070(17) C5B1 0.067(2) 0.061(2) 0.131(3) 0.005(2) -0.010(2) -0.0057(19) C5G1 0.103(3) 0.075(3) 0.199(6) -0.011(4) -0.018(4) -0.014(3) C5G2 0.093(3) 0.102(4) 0.187(6) 0.041(4) 0.041(3) -0.005(3) C5B2 0.092(3) 0.070(3) 0.123(3) 0.002(2) -0.009(3) 0.017(2) C5 0.0510(15) 0.0622(19) 0.0641(18) -0.0009(15) 0.0031(13) 0.0004(15) O5 0.0821(15) 0.0876(19) 0.0671(14) -0.0007(13) -0.0049(12) 0.0076(15) N6 0.0607(14) 0.0527(15) 0.0657(14) -0.0060(12) -0.0031(11) -0.0021(12) C6A 0.075(2) 0.0545(18) 0.077(2) -0.0109(16) 0.0018(16) 0.0013(16) C6B 0.102(3) 0.083(3) 0.124(4) -0.026(3) -0.007(3) 0.021(3) C6G1 0.087(4) 0.163(8) 0.265(10) -0.039(7) 0.050(5) 0.012(4) C6G2 0.175(7) 0.073(4) 0.224(8) -0.024(4) -0.018(6) 0.046(4) C6 0.099(3) 0.055(2) 0.081(2) -0.0022(18) 0.008(2) -0.004(2) O6 0.157(3) 0.119(3) 0.097(2) -0.010(2) 0.042(2) -0.046(3) OTC 0.108(2) 0.0681(18) 0.0997(19) -0.0084(15) 0.0066(15) -0.0299(16) CTC 0.133(4) 0.086(4) 0.163(5) -0.006(4) 0.023(4) -0.044(3) _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 C01A C0A 1.483(7) . ? C0A O0A 1.199(5) . ? C0A O01 1.350(5) . ? O01 C1A 1.459(4) . ? C1A C1B2 1.524(5) . ? C1A C1 1.540(5) . ? C1A C1B1 1.540(5) . ? C1B1 C1G2 1.510(6) . ? C1B1 C1G1 1.534(5) . ? C1 O1 1.219(4) . ? C1 N2 1.324(4) . ? N2 C2A 1.446(4) . ? C2A C2 1.500(7) . ? C2A C2B 1.530(5) . ? C2B C2G2 1.500(8) . ? C2B C2G1 1.520(6) . ? C2 O2 1.202(5) . ? C2 OTA 1.318(6) . ? OTA CTA 1.454(9) . ? C01B C0B 1.474(7) . ? C0B O0B 1.184(5) . ? C0B O03 1.342(5) . ? O03 C3A 1.464(4) . ? C3A C3B2 1.522(5) . ? C3A C3B1 1.535(5) . ? C3A C3 1.542(5) . ? C3B1 C3G1 1.510(7) . ? C3B1 C3G2 1.520(6) . ? C3 O3 1.210(4) . ? C3 N4 1.326(4) . ? N4 C4A 1.461(5) . ? C4A C4 1.485(7) . ? C4A C4B 1.522(6) . ? C4B C4G2 1.528(8) . ? C4B C4G1 1.529(7) . ? C4 O4 1.184(5) . ? C4 OTB 1.297(6) . ? OTB CTB 1.473(9) . ? C01C C0C 1.473(6) . ? C0C O0C 1.191(5) . ? C0C O05 1.344(6) . ? O05 C5A 1.442(5) . ? C5A C5B2 1.517(6) . ? C5A C5 1.533(5) . ? C5A C5B1 1.566(6) . ? C5B1 C5G2 1.506(8) . ? C5B1 C5G1 1.522(7) . ? C5 O5 1.204(4) . ? C5 N6 1.326(4) . ? N6 C6A 1.459(5) . ? C6A C6 1.512(6) . ? C6A C6B 1.553(6) . ? C6B C6G1 1.514(10) . ? C6B C6G2 1.547(8) . ? C6 O6 1.160(5) . ? C6 OTC 1.340(5) . ? OTC CTC 1.466(7) . ? 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 O0A C0A O01 123.6(4) . . ? O0A C0A C01A 125.7(4) . . ? O01 C0A C01A 110.6(4) . . ? C0A O01 C1A 118.5(3) . . ? O01 C1A C1B2 111.0(3) . . ? O01 C1A C1 108.9(3) . . ? C1B2 C1A C1 111.2(3) . . ? O01 C1A C1B1 103.4(2) . . ? C1B2 C1A C1B1 113.2(3) . . ? C1 C1A C1B1 108.7(3) . . ? C1G2 C1B1 C1G1 110.3(4) . . ? C1G2 C1B1 C1A 113.6(3) . . ? C1G1 C1B1 C1A 112.6(3) . . ? O1 C1 N2 123.0(3) . . ? O1 C1 C1A 120.9(3) . . ? N2 C1 C1A 115.9(3) . . ? C1 N2 C2A 122.7(3) . . ? N2 C2A C2 111.1(3) . . ? N2 C2A C2B 111.4(3) . . ? C2 C2A C2B 111.6(3) . . ? C2G2 C2B C2G1 110.3(4) . . ? C2G2 C2B C2A 110.1(4) . . ? C2G1 C2B C2A 110.9(3) . . ? O2 C2 OTA 123.8(5) . . ? O2 C2 C2A 123.7(5) . . ? OTA C2 C2A 112.5(3) . . ? C2 OTA CTA 118.6(6) . . ? O0B C0B O03 123.2(4) . . ? O0B C0B C01B 125.6(5) . . ? O03 C0B C01B 111.2(4) . . ? C0B O03 C3A 120.3(3) . . ? O03 C3A C3B2 110.5(3) . . ? O03 C3A C3B1 103.8(3) . . ? C3B2 C3A C3B1 113.2(3) . . ? O03 C3A C3 109.4(3) . . ? C3B2 C3A C3 111.0(3) . . ? C3B1 C3A C3 108.6(3) . . ? C3G1 C3B1 C3G2 110.9(4) . . ? C3G1 C3B1 C3A 113.0(3) . . ? C3G2 C3B1 C3A 112.6(4) . . ? O3 C3 N4 123.7(3) . . ? O3 C3 C3A 120.4(3) . . ? N4 C3 C3A 115.8(3) . . ? C3 N4 C4A 121.4(3) . . ? N4 C4A C4 112.6(4) . . ? N4 C4A C4B 113.0(3) . . ? C4 C4A C4B 110.2(3) . . ? C4A C4B C4G2 110.8(4) . . ? C4A C4B C4G1 110.7(4) . . ? C4G2 C4B C4G1 108.4(5) . . ? O4 C4 OTB 124.8(5) . . ? O4 C4 C4A 124.0(5) . . ? OTB C4 C4A 111.3(3) . . ? C4 OTB CTB 116.0(5) . . ? O0C C0C O05 123.3(4) . . ? O0C C0C C01C 125.0(5) . . ? O05 C0C C01C 111.6(4) . . ? C0C O05 C5A 118.6(3) . . ? O05 C5A C5B2 112.2(4) . . ? O05 C5A C5 110.3(3) . . ? C5B2 C5A C5 110.8(3) . . ? O05 C5A C5B1 101.9(3) . . ? C5B2 C5A C5B1 111.2(4) . . ? C5 C5A C5B1 110.1(3) . . ? C5G2 C5B1 C5G1 113.7(5) . . ? C5G2 C5B1 C5A 112.0(4) . . ? C5G1 C5B1 C5A 112.8(4) . . ? O5 C5 N6 123.6(3) . . ? O5 C5 C5A 121.5(3) . . ? N6 C5 C5A 114.6(2) . . ? C5 N6 C6A 122.4(3) . . ? N6 C6A C6 109.6(3) . . ? N6 C6A C6B 109.3(3) . . ? C6 C6A C6B 111.9(4) . . ? C6G1 C6B C6G2 109.8(7) . . ? C6G1 C6B C6A 110.1(5) . . ? C6G2 C6B C6A 110.4(5) . . ? O6 C6 OTC 124.7(4) . . ? O6 C6 C6A 126.2(4) . . ? OTC C6 C6A 109.1(3) . . ? C6 OTC CTC 114.1(4) . . ? 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 O0A C0A O01 C1A -3.8(6) . . . . ? C01A C0A O01 C1A 174.2(3) . . . . y C0A O01 C1A C1B2 68.5(4) . . . . ? C0A O01 C1A C1 -54.3(4) . . . . y C0A O01 C1A C1B1 -169.7(3) . . . . ? O01 C1A C1B1 C1G2 173.1(3) . . . . y C1B2 C1A C1B1 C1G2 -66.6(4) . . . . ? C1 C1A C1B1 C1G2 57.5(4) . . . . ? O01 C1A C1B1 C1G1 -60.5(4) . . . . y C1B2 C1A C1B1 C1G1 59.7(4) . . . . ? C1 C1A C1B1 C1G1 -176.2(3) . . . . ? O01 C1A C1 O1 141.7(3) . . . . ? C1B2 C1A C1 O1 19.1(5) . . . . ? C1B1 C1A C1 O1 -106.2(4) . . . . ? O01 C1A C1 N2 -43.8(4) . . . . y C1B2 C1A C1 N2 -166.5(3) . . . . ? C1B1 C1A C1 N2 68.3(4) . . . . ? O1 C1 N2 C2A -3.6(6) . . . . ? C1A C1 N2 C2A -178.0(3) . . . . y C1 N2 C2A C2 -91.5(4) . . . . y C1 N2 C2A C2B 143.5(4) . . . . ? N2 C2A C2B C2G2 -58.3(5) . . . . y C2 C2A C2B C2G2 176.9(4) . . . . ? N2 C2A C2B C2G1 179.3(4) . . . . y C2 C2A C2B C2G1 54.6(5) . . . . ? N2 C2A C2 O2 137.4(4) . . . . ? C2B C2A C2 O2 -97.7(5) . . . . ? N2 C2A C2 OTA -44.5(4) . . . . y C2B C2A C2 OTA 80.4(4) . . . . ? O2 C2 OTA CTA -3.8(8) . . . . ? C2A C2 OTA CTA 178.1(6) . . . . y O0B C0B O03 C3A 0.5(7) . . . . ? C01B C0B O03 C3A -178.2(4) . . . . y C0B O03 C3A C3B2 67.7(4) . . . . ? C0B O03 C3A C3B1 -170.6(3) . . . . ? C0B O03 C3A C3 -54.8(4) . . . . y O03 C3A C3B1 C3G1 173.6(3) . . . . y C3B2 C3A C3B1 C3G1 -66.6(4) . . . . ? C3 C3A C3B1 C3G1 57.2(4) . . . . ? O03 C3A C3B1 C3G2 -59.7(4) . . . . y C3B2 C3A C3B1 C3G2 60.1(5) . . . . ? C3 C3A C3B1 C3G2 -176.1(3) . . . . ? O03 C3A C3 O3 139.2(3) . . . . ? C3B2 C3A C3 O3 17.0(5) . . . . ? C3B1 C3A C3 O3 -108.1(4) . . . . ? O03 C3A C3 N4 -45.0(4) . . . . y C3B2 C3A C3 N4 -167.2(3) . . . . ? C3B1 C3A C3 N4 67.7(4) . . . . ? O3 C3 N4 C4A -1.3(6) . . . . ? C3A C3 N4 C4A -177.0(4) . . . . y C3 N4 C4A C4 -98.5(4) . . . . y C3 N4 C4A C4B 135.8(4) . . . . ? N4 C4A C4B C4G2 -53.5(5) . . . . y C4 C4A C4B C4G2 179.5(5) . . . . ? N4 C4A C4B C4G1 -173.7(4) . . . . y C4 C4A C4B C4G1 59.3(5) . . . . ? N4 C4A C4 O4 131.3(5) . . . . ? C4B C4A C4 O4 -101.5(6) . . . . ? N4 C4A C4 OTB -48.7(5) . . . . y C4B C4A C4 OTB 78.5(5) . . . . ? O4 C4 OTB CTB 2.0(9) . . . . ? C4A C4 OTB CTB -178.0(6) . . . . y O0C C0C O05 C5A -1.7(7) . . . . ? C01C C0C O05 C5A 176.5(5) . . . . y C0C O05 C5A C5B2 68.2(5) . . . . ? C0C O05 C5A C5 -55.9(4) . . . . y C0C O05 C5A C5B1 -172.8(4) . . . . ? O05 C5A C5B1 C5G2 169.4(4) . . . . y C5B2 C5A C5B1 C5G2 -70.9(5) . . . . ? C5 C5A C5B1 C5G2 52.3(5) . . . . ? O05 C5A C5B1 C5G1 -60.9(5) . . . . y C5B2 C5A C5B1 C5G1 58.9(6) . . . . ? C5 C5A C5B1 C5G1 -177.9(5) . . . . ? O05 C5A C5 O5 138.7(3) . . . . y C5B2 C5A C5 O5 13.8(6) . . . . ? C5B1 C5A C5 O5 -109.6(4) . . . . ? O05 C5A C5 N6 -47.3(4) . . . . y C5B2 C5A C5 N6 -172.1(4) . . . . ? C5B1 C5A C5 N6 64.4(4) . . . . ? O5 C5 N6 C6A -6.4(5) . . . . ? C5A C5 N6 C6A 179.7(3) . . . . y C5 N6 C6A C6 -95.1(4) . . . . y C5 N6 C6A C6B 141.8(4) . . . . ? N6 C6A C6B C6G1 -68.6(6) . . . . y C6 C6A C6B C6G1 169.8(5) . . . . ? N6 C6A C6B C6G2 170.0(6) . . . . y C6 C6A C6B C6G2 48.4(7) . . . . ? N6 C6A C6 O6 -42.5(6) . . . . ? C6B C6A C6 O6 79.0(6) . . . . ? N6 C6A C6 OTC 138.6(3) . . . . y C6B C6A C6 OTC -100.0(4) . . . . ? O6 C6 OTC CTC -2.2(7) . . . . ? C6A C6 OTC CTC 176.8(4) . . . . y 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 N2 H2 O5 0.86 2.22 3.075(5) 170.9 1_656 N4 H4 O1 0.86 2.16 2.999(4) 165.7 . N6 H6 O3 0.86 2.13 2.979(4) 169.9 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 60.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.312 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.049 #===END=== data_ctf99 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Ac-L-(\aMe)Hyv-(Aib)4-OMe' _chemical_melting_point 476-477 _chemical_formula_moiety ? _chemical_formula_sum 'C25 H44 N4 O8' _chemical_formula_weight 528.64 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 Triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 8.281(2) _cell_length_b 9.539(3) _cell_length_c 10.417(3) _cell_angle_alpha 99.18(5) _cell_angle_beta 96.34(4) _cell_angle_gamma 109.03(5) _cell_volume 756.2(4) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 48 _cell_measurement_theta_min 12 _cell_measurement_theta_max 20 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.161 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 286 _exptl_absorpt_coefficient_mu 0.714 _exptl_absorpt_correction_type 'not carried out' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Philips PW1100 diffractometer' _diffrn_measurement_method '\q-2\q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% negligible _diffrn_reflns_number 2258 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.37 _diffrn_reflns_theta_max 59.99 _reflns_number_total 2255 _reflns_number_gt 1572 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material ? _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 fullcycle _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1833P)^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 constrained _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 0.0(6) _refine_ls_number_reflns 2255 _refine_ls_number_parameters 334 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1029 _refine_ls_R_factor_gt 0.0807 _refine_ls_wR_factor_ref 0.2265 _refine_ls_wR_factor_gt 0.2074 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _refine_ls_shift/su_max 0.107 _refine_ls_shift/su_mean 0.031 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 C01 C 0.7811(14) 1.0379(12) -0.2063(11) 0.124(3) Uani 1 1 d . . . H01A H 0.8372 1.1320 -0.1437 0.187 Uiso 1 1 calc R . . H01B H 0.7290 1.0567 -0.2858 0.187 Uiso 1 1 calc R . . H01C H 0.8651 0.9919 -0.2262 0.187 Uiso 1 1 calc R . . C0 C 0.6433(10) 0.9334(8) -0.1488(8) 0.093(2) Uani 1 1 d . . . O0 O 0.6731(9) 0.8887(7) -0.0532(6) 0.122(2) Uani 1 1 d . . . O01 O 0.4862(6) 0.8892(5) -0.2247(4) 0.0842(13) Uani 1 1 d . . . C1A C 0.3349(9) 0.8153(7) -0.1720(6) 0.0784(18) Uani 1 1 d . . . C1B1 C 0.1859(10) 0.7625(9) -0.2900(8) 0.088(2) Uani 1 1 d . . . H1B1 H 0.2137 0.6939 -0.3573 0.106 Uiso 1 1 calc R . . C1G1 C 0.1661(15) 0.8914(12) -0.3535(9) 0.120(3) Uani 1 1 d . . . H1G1 H 0.1417 0.9629 -0.2899 0.180 Uiso 1 1 calc R . . H1G2 H 0.0725 0.8508 -0.4275 0.180 Uiso 1 1 calc R . . H1G3 H 0.2718 0.9414 -0.3831 0.180 Uiso 1 1 calc R . . C1G2 C 0.0137(14) 0.6732(12) -0.2576(11) 0.125(3) Uani 1 1 d . . . H1G4 H 0.0177 0.5793 -0.2381 0.187 Uiso 1 1 calc R . . H1G5 H -0.0764 0.6528 -0.3318 0.187 Uiso 1 1 calc R . . H1G6 H -0.0098 0.7309 -0.1823 0.187 Uiso 1 1 calc R . . C1B2 C 0.3142(13) 0.9283(10) -0.0588(8) 0.103(3) Uani 1 1 d . . . H1B2 H 0.4187 0.9687 0.0059 0.155 Uiso 1 1 calc R . . H1B3 H 0.2188 0.8777 -0.0185 0.155 Uiso 1 1 calc R . . H1B4 H 0.2921 1.0095 -0.0926 0.155 Uiso 1 1 calc R . . C1 C 0.3524(9) 0.6742(8) -0.1234(6) 0.0779(17) Uani 1 1 d . . . O1 O 0.3110(7) 0.6507(6) -0.0160(5) 0.0947(15) Uani 1 1 d . . . N2 N 0.3995(8) 0.5784(6) -0.2037(5) 0.0782(15) Uani 1 1 d . . . H2 H 0.4356 0.6032 -0.2740 0.094 Uiso 1 1 calc R . . C2A C 0.3915(10) 0.4323(8) -0.1758(7) 0.0831(19) Uani 1 1 d . . . C2B1 C 0.2068(12) 0.3263(10) -0.1872(9) 0.102(2) Uani 1 1 d . . . H2B1 H 0.1493 0.3717 -0.1270 0.153 Uiso 1 1 calc R . . H2B2 H 0.2074 0.2321 -0.1661 0.153 Uiso 1 1 calc R . . H2B3 H 0.1466 0.3079 -0.2759 0.153 Uiso 1 1 calc R . . C2B2 C 0.4840(14) 0.3614(10) -0.2703(8) 0.106(3) Uani 1 1 d . . . H2B4 H 0.4125 0.3241 -0.3562 0.159 Uiso 1 1 calc R . . H2B5 H 0.5060 0.2791 -0.2387 0.159 Uiso 1 1 calc R . . H2B6 H 0.5920 0.4364 -0.2759 0.159 Uiso 1 1 calc R . . C2 C 0.4963(10) 0.4502(8) -0.0365(7) 0.0815(18) Uani 1 1 d . . . O2 O 0.4441(7) 0.3526(5) 0.0291(5) 0.0923(15) Uani 1 1 d . . . N3 N 0.6404(7) 0.5672(7) 0.0037(5) 0.0837(16) Uani 1 1 d . . . H3 H 0.6653 0.6349 -0.0436 0.100 Uiso 1 1 calc R . . C3A C 0.7613(9) 0.5887(9) 0.1249(7) 0.0853(19) Uani 1 1 d . . . C3B1 C 0.8397(12) 0.4641(10) 0.1145(9) 0.106(3) Uani 1 1 d . . . H3B1 H 0.7486 0.3670 0.0976 0.159 Uiso 1 1 calc R . . H3B2 H 0.9153 0.4774 0.1957 0.159 Uiso 1 1 calc R . . H3B3 H 0.9047 0.4694 0.0434 0.159 Uiso 1 1 calc R . . C3B2 C 0.9013(11) 0.7433(11) 0.1449(10) 0.113(3) Uani 1 1 d . . . H3B4 H 0.9632 0.7464 0.0721 0.169 Uiso 1 1 calc R . . H3B5 H 0.9804 0.7617 0.2255 0.169 Uiso 1 1 calc R . . H3B6 H 0.8490 0.8198 0.1496 0.169 Uiso 1 1 calc R . . C3 C 0.6681(10) 0.5913(8) 0.2470(7) 0.0844(19) Uani 1 1 d . . . O3 O 0.7162(8) 0.5472(7) 0.3404(5) 0.1053(17) Uani 1 1 d . . . N4 N 0.5471(7) 0.6547(6) 0.2410(5) 0.0804(15) Uani 1 1 d . . . H4 H 0.5179 0.6823 0.1700 0.096 Uiso 1 1 calc R . . C4A C 0.4643(10) 0.6773(8) 0.3541(7) 0.0807(18) Uani 1 1 d . . . C4B1 C 0.5896(13) 0.7816(10) 0.4712(8) 0.107(3) Uani 1 1 d . . . H4B1 H 0.6630 0.7318 0.5061 0.160 Uiso 1 1 calc R . . H4B2 H 0.5273 0.8091 0.5375 0.160 Uiso 1 1 calc R . . H4B3 H 0.6594 0.8712 0.4455 0.160 Uiso 1 1 calc R . . C4B2 C 0.3210(12) 0.7390(9) 0.3092(8) 0.099(2) Uani 1 1 d . . . H4B4 H 0.3726 0.8330 0.2824 0.149 Uiso 1 1 calc R . . H4B5 H 0.2616 0.7555 0.3811 0.149 Uiso 1 1 calc R . . H4B6 H 0.2399 0.6668 0.2362 0.149 Uiso 1 1 calc R . . C4 C 0.3690(10) 0.5206(8) 0.3857(7) 0.0832(19) Uani 1 1 d . . . O4 O 0.3480(7) 0.5102(5) 0.5005(5) 0.0934(15) Uani 1 1 d . . . N5 N 0.2975(8) 0.4062(6) 0.2846(5) 0.0853(16) Uani 1 1 d . . . H5 H 0.3010 0.4261 0.2071 0.102 Uiso 1 1 calc R . . C5A C 0.2116(11) 0.2462(8) 0.2926(7) 0.091(2) Uani 1 1 d . . . C5B1 C 0.3451(16) 0.1774(12) 0.3319(12) 0.128(3) Uani 1 1 d . . . H5B1 H 0.4147 0.1751 0.2643 0.192 Uiso 1 1 calc R . . H5B2 H 0.2875 0.0760 0.3426 0.192 Uiso 1 1 calc R . . H5B3 H 0.4179 0.2373 0.4136 0.192 Uiso 1 1 calc R . . C5B2 C 0.1033(15) 0.1657(9) 0.1580(10) 0.122(3) Uani 1 1 d . . . H5B4 H 0.0413 0.2266 0.1273 0.184 Uiso 1 1 calc R . . H5B5 H 0.0223 0.0696 0.1642 0.184 Uiso 1 1 calc R . . H5B6 H 0.1778 0.1499 0.0971 0.184 Uiso 1 1 calc R . . C5 C 0.0882(11) 0.2335(8) 0.3889(8) 0.098(2) Uani 1 1 d . . . O5 O 0.0755(9) 0.1508(7) 0.4669(6) 0.1162(19) Uani 1 1 d . . . OT O -0.0120(7) 0.3148(6) 0.3746(6) 0.1026(17) Uani 1 1 d . . . CT C -0.1392(15) 0.2994(16) 0.4545(13) 0.141(4) Uani 1 1 d . . . HT1 H -0.1881 0.1953 0.4612 0.212 Uiso 1 1 calc R . . HT2 H -0.2289 0.3312 0.4164 0.212 Uiso 1 1 calc R . . HT3 H -0.0879 0.3612 0.5410 0.212 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 C01 0.111(6) 0.112(6) 0.130(8) 0.024(6) 0.004(6) 0.018(5) C0 0.100(6) 0.081(5) 0.094(5) 0.014(4) 0.000(5) 0.033(4) O0 0.129(5) 0.111(4) 0.118(4) 0.041(4) -0.026(4) 0.037(4) O01 0.102(3) 0.081(3) 0.075(3) 0.025(2) 0.011(3) 0.037(3) C1A 0.102(5) 0.078(4) 0.069(4) 0.026(3) 0.018(4) 0.043(4) C1B1 0.096(5) 0.088(4) 0.093(5) 0.035(4) 0.011(4) 0.043(4) C1G1 0.161(9) 0.129(7) 0.103(6) 0.045(5) 0.007(6) 0.090(7) C1G2 0.126(7) 0.124(7) 0.134(8) 0.057(6) 0.005(6) 0.049(6) C1B2 0.138(7) 0.110(6) 0.086(5) 0.026(5) 0.035(5) 0.069(6) C1 0.086(4) 0.082(4) 0.068(4) 0.022(3) 0.003(3) 0.033(4) O1 0.122(4) 0.098(3) 0.079(3) 0.033(3) 0.019(3) 0.052(3) N2 0.106(4) 0.073(3) 0.064(3) 0.022(3) 0.004(3) 0.042(3) C2A 0.103(5) 0.078(4) 0.078(4) 0.026(3) 0.004(4) 0.043(4) C2B1 0.112(6) 0.091(5) 0.095(5) 0.026(4) -0.010(5) 0.032(5) C2B2 0.162(8) 0.102(5) 0.079(5) 0.029(4) 0.006(5) 0.080(6) C2 0.096(5) 0.084(5) 0.073(4) 0.029(4) 0.007(4) 0.040(4) O2 0.116(4) 0.081(3) 0.082(3) 0.032(2) 0.005(3) 0.033(3) N3 0.089(4) 0.092(4) 0.079(4) 0.038(3) 0.009(3) 0.036(3) C3A 0.081(4) 0.099(5) 0.085(5) 0.034(4) 0.010(4) 0.037(4) C3B1 0.118(6) 0.112(6) 0.108(6) 0.041(5) 0.014(5) 0.059(5) C3B2 0.094(5) 0.131(7) 0.109(6) 0.049(6) -0.002(5) 0.030(5) C3 0.098(5) 0.074(4) 0.087(5) 0.027(4) -0.009(4) 0.040(4) O3 0.122(4) 0.130(4) 0.092(3) 0.050(3) 0.009(3) 0.072(4) N4 0.098(4) 0.078(3) 0.073(3) 0.023(3) 0.003(3) 0.041(3) C4A 0.099(5) 0.071(4) 0.076(4) 0.022(3) 0.003(4) 0.036(4) C4B1 0.124(7) 0.096(5) 0.086(5) 0.007(4) 0.010(5) 0.027(5) C4B2 0.134(7) 0.100(5) 0.097(5) 0.040(4) 0.025(5) 0.076(5) C4 0.096(5) 0.087(5) 0.072(4) 0.030(4) 0.001(4) 0.038(4) O4 0.120(4) 0.090(3) 0.075(3) 0.025(2) 0.009(3) 0.041(3) N5 0.107(4) 0.070(3) 0.068(3) 0.013(3) -0.004(3) 0.024(3) C5A 0.117(6) 0.067(4) 0.091(5) 0.021(4) 0.015(5) 0.034(4) C5B1 0.152(8) 0.106(6) 0.148(9) 0.039(6) 0.041(7) 0.065(6) C5B2 0.146(8) 0.082(5) 0.114(7) 0.013(5) 0.006(6) 0.016(5) C5 0.114(6) 0.077(4) 0.104(6) 0.044(4) 0.000(5) 0.029(4) O5 0.140(5) 0.107(4) 0.122(4) 0.055(4) 0.023(4) 0.055(4) OT 0.111(4) 0.111(4) 0.112(4) 0.058(3) 0.022(3) 0.055(3) CT 0.139(9) 0.177(11) 0.162(10) 0.100(9) 0.050(8) 0.088(8) _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 C01 C0 1.501(13) . ? C0 O0 1.177(9) . ? C0 O01 1.343(9) . ? O01 C1A 1.438(8) . ? C1A C1B1 1.533(10) . ? C1A C1B2 1.530(11) . ? C1A C1 1.555(9) . ? C1B1 C1G2 1.509(13) . ? C1B1 C1G1 1.532(11) . ? C1 O1 1.238(8) . ? C1 N2 1.322(9) . ? N2 C2A 1.451(9) . ? C2A C2B1 1.513(12) . ? C2A C2B2 1.518(12) . ? C2A C2 1.560(10) . ? C2 O2 1.236(8) . ? C2 N3 1.310(9) . ? N3 C3A 1.465(9) . ? C3A C3B2 1.516(13) . ? C3A C3B1 1.524(11) . ? C3A C3 1.560(12) . ? C3 O3 1.199(8) . ? C3 N4 1.329(9) . ? N4 C4A 1.448(10) . ? C4A C4B1 1.488(11) . ? C4A C4 1.553(10) . ? C4A C4B2 1.548(10) . ? C4 O4 1.242(8) . ? C4 N5 1.313(9) . ? N5 C5A 1.480(9) . ? C5A C5B1 1.510(14) . ? C5A C5 1.499(13) . ? C5A C5B2 1.513(13) . ? C5 O5 1.209(9) . ? C5 OT 1.320(9) . ? OT CT 1.399(12) . ? 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 O0 C0 O01 124.6(8) . . ? O0 C0 C01 123.3(8) . . ? O01 C0 C01 111.9(7) . . ? C0 O01 C1A 119.1(5) . . ? O01 C1A C1B1 104.4(5) . . ? O01 C1A C1B2 109.0(6) . . ? C1B1 C1A C1B2 113.5(6) . . ? O01 C1A C1 110.0(5) . . ? C1B1 C1A C1 109.0(5) . . ? C1B2 C1A C1 110.9(6) . . ? C1G2 C1B1 C1A 113.1(6) . . ? C1G2 C1B1 C1G1 109.3(7) . . ? C1A C1B1 C1G1 113.6(7) . . ? O1 C1 N2 122.7(6) . . ? O1 C1 C1A 119.2(6) . . ? N2 C1 C1A 117.9(5) . . ? C1 N2 C2A 121.4(6) . . ? N2 C2A C2B1 112.1(6) . . ? N2 C2A C2B2 109.1(6) . . ? C2B1 C2A C2B2 109.9(7) . . ? N2 C2A C2 111.3(6) . . ? C2B1 C2A C2 110.0(6) . . ? C2B2 C2A C2 104.1(6) . . ? O2 C2 N3 122.9(6) . . ? O2 C2 C2A 119.4(6) . . ? N3 C2 C2A 117.7(6) . . ? C2 N3 C3A 123.4(6) . . ? N3 C3A C3B2 107.8(6) . . ? N3 C3A C3B1 110.4(7) . . ? C3B2 C3A C3B1 110.9(7) . . ? N3 C3A C3 110.5(6) . . ? C3B2 C3A C3 106.6(7) . . ? C3B1 C3A C3 110.5(6) . . ? O3 C3 N4 125.2(8) . . ? O3 C3 C3A 119.4(6) . . ? N4 C3 C3A 115.2(6) . . ? C3 N4 C4A 120.0(6) . . ? N4 C4A C4B1 112.3(7) . . ? N4 C4A C4 108.8(6) . . ? C4B1 C4A C4 111.2(6) . . ? N4 C4A C4B2 106.3(5) . . ? C4B1 C4A C4B2 111.8(7) . . ? C4 C4A C4B2 106.0(6) . . ? O4 C4 N5 122.7(7) . . ? O4 C4 C4A 120.2(7) . . ? N5 C4 C4A 116.8(6) . . ? C4 N5 C5A 125.6(6) . . ? N5 C5A C5B1 110.4(7) . . ? N5 C5A C5 110.9(6) . . ? C5B1 C5A C5 110.1(7) . . ? N5 C5A C5B2 106.5(6) . . ? C5B1 C5A C5B2 112.1(8) . . ? C5 C5A C5B2 106.7(8) . . ? O5 C5 OT 123.4(9) . . ? O5 C5 C5A 123.3(8) . . ? OT C5 C5A 113.2(6) . . ? C5 OT CT 116.2(6) . . ? 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 O0 C0 O01 C1A 17.5(11) . . . . ? C01 C0 O01 C1A -167.1(7) . . . . y C0 O01 C1A C1B1 -172.3(6) . . . . ? C0 O01 C1A C1B2 66.1(8) . . . . ? C0 O01 C1A C1 -55.6(7) . . . . y O01 C1A C1B1 C1G2 176.8(7) . . . . y C1B2 C1A C1B1 C1G2 -64.7(8) . . . . ? C1 C1A C1B1 C1G2 59.4(8) . . . . ? O01 C1A C1B1 C1G1 -57.8(8) . . . . y C1B2 C1A C1B1 C1G1 60.7(9) . . . . ? C1 C1A C1B1 C1G1 -175.2(7) . . . . ? O01 C1A C1 O1 136.2(6) . . . . ? C1B1 C1A C1 O1 -109.9(7) . . . . ? C1B2 C1A C1 O1 15.6(9) . . . . ? O01 C1A C1 N2 -48.5(8) . . . . y C1B1 C1A C1 N2 65.4(8) . . . . ? C1B2 C1A C1 N2 -169.1(7) . . . . ? O1 C1 N2 C2A 5.3(11) . . . . ? C1A C1 N2 C2A -169.8(6) . . . . y C1 N2 C2A C2B1 68.4(8) . . . . ? C1 N2 C2A C2B2 -169.6(7) . . . . ? C1 N2 C2A C2 -55.3(9) . . . . y N2 C2A C2 O2 145.8(7) . . . . ? C2B1 C2A C2 O2 20.9(10) . . . . ? C2B2 C2A C2 O2 -96.9(8) . . . . ? N2 C2A C2 N3 -36.5(9) . . . . y C2B1 C2A C2 N3 -161.4(7) . . . . ? C2B2 C2A C2 N3 80.8(8) . . . . ? O2 C2 N3 C3A 4.9(11) . . . . ? C2A C2 N3 C3A -172.7(6) . . . . y C2 N3 C3A C3B2 -174.2(7) . . . . ? C2 N3 C3A C3B1 64.6(9) . . . . ? C2 N3 C3A C3 -58.0(9) . . . . y N3 C3A C3 O3 150.0(7) . . . . ? C3B2 C3A C3 O3 -93.1(8) . . . . ? C3B1 C3A C3 O3 27.4(10) . . . . ? N3 C3A C3 N4 -34.8(9) . . . . y C3B2 C3A C3 N4 82.0(7) . . . . ? C3B1 C3A C3 N4 -157.4(7) . . . . ? O3 C3 N4 C4A 1.1(11) . . . . ? C3A C3 N4 C4A -173.8(6) . . . . y C3 N4 C4A C4B1 62.4(8) . . . . ? C3 N4 C4A C4 -61.2(8) . . . . y C3 N4 C4A C4B2 -175.0(6) . . . . ? N4 C4A C4 O4 151.7(7) . . . . ? C4B1 C4A C4 O4 27.4(10) . . . . ? C4B2 C4A C4 O4 -94.4(8) . . . . ? N4 C4A C4 N5 -35.4(9) . . . . y C4B1 C4A C4 N5 -159.6(7) . . . . ? C4B2 C4A C4 N5 78.6(8) . . . . ? O4 C4 N5 C5A -11.8(12) . . . . ? C4A C4 N5 C5A 175.5(7) . . . . y C4 N5 C5A C5B1 -75.1(10) . . . . ? C4 N5 C5A C5 47.2(10) . . . . y C4 N5 C5A C5B2 162.9(8) . . . . ? N5 C5A C5 O5 -137.7(8) . . . . ? C5B1 C5A C5 O5 -15.3(12) . . . . ? C5B2 C5A C5 O5 106.7(9) . . . . ? N5 C5A C5 OT 46.0(9) . . . . y C5B1 C5A C5 OT 168.5(7) . . . . ? C5B2 C5A C5 OT -69.5(8) . . . . ? O5 C5 OT CT -0.9(13) . . . . ? C5A C5 OT CT 175.4(9) . . . . y 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 N3 H3 O0 0.86 2.42 3.147(9) 142.8 . N4 H4 O1 0.86 2.35 3.123(7) 149.8 . N5 H5 O2 0.86 2.44 3.083(8) 132.3 . N2 H2 O4 0.86 2.32 2.998(7) 136.3 1_554 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 59.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.311 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.069 #===END=== data_mc01 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Ac-(Aib)5-OMe _chemical_melting_point 551-552 _chemical_formula_moiety ? _chemical_formula_sum 'C23 H41 N5 O7' _chemical_formula_weight 499.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 18.687(4) _cell_length_b 8.326(2) _cell_length_c 19.443(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.99(7) _cell_angle_gamma 90.00 _cell_volume 2908.1(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 48 _cell_measurement_theta_min 12 _cell_measurement_theta_max 20 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.141 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.700 _exptl_absorpt_correction_type 'not carried out' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Philips PW1100 diffractometer' _diffrn_measurement_method '\q-2\q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% negligible _diffrn_reflns_number 5107 _diffrn_reflns_av_R_equivalents 0.0757 _diffrn_reflns_av_sigmaI/netI 0.1207 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 60.00 _reflns_number_total 4306 _reflns_number_gt 1605 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material ? _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 fullcycle _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1337P)^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 constrained _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4306 _refine_ls_number_parameters 316 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.2048 _refine_ls_R_factor_gt 0.0829 _refine_ls_wR_factor_ref 0.2373 _refine_ls_wR_factor_gt 0.1954 _refine_ls_goodness_of_fit_ref 0.850 _refine_ls_restrained_S_all 0.850 _refine_ls_shift/su_max 0.129 _refine_ls_shift/su_mean 0.033 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 C01 C -0.0582(3) 0.5926(8) 0.8380(3) 0.114(2) Uani 1 1 d . . . H01A H -0.0988 0.5787 0.8588 0.171 Uiso 1 1 calc R . . H01B H -0.0730 0.5571 0.7892 0.171 Uiso 1 1 calc R . . H01C H -0.0447 0.7041 0.8397 0.171 Uiso 1 1 calc R . . C0 C 0.0072(3) 0.4959(7) 0.8793(3) 0.0827(16) Uani 1 1 d . . . O0 O 0.05566(18) 0.5522(5) 0.92918(19) 0.0966(12) Uani 1 1 d . . . N1 N 0.0089(2) 0.3409(5) 0.8601(2) 0.0782(12) Uani 1 1 d . . . H1 H -0.0219 0.3097 0.8208 0.094 Uiso 1 1 calc R . . C1A C 0.0603(3) 0.2228(6) 0.9028(2) 0.0715(14) Uani 1 1 d D . . C1B1 C 0.0497(3) 0.0663(6) 0.8593(3) 0.116(2) Uani 1 1 d D . . H1B1 H -0.0012 0.0319 0.8495 0.174 Uiso 1 1 calc R . . H1B2 H 0.0817 -0.0153 0.8862 0.174 Uiso 1 1 calc R . . H1B3 H 0.0617 0.0844 0.8150 0.174 Uiso 1 1 calc R . . C1B2 C 0.0408(3) 0.1970(9) 0.9738(3) 0.116(2) Uani 1 1 d D . . H1B4 H 0.0491 0.2949 1.0009 0.174 Uiso 1 1 calc R . . H1B5 H 0.0717 0.1136 1.0007 0.174 Uiso 1 1 calc R . . H1B6 H -0.0105 0.1663 0.9642 0.174 Uiso 1 1 calc R . . C1 C 0.1397(2) 0.2736(6) 0.9158(2) 0.0649(13) Uani 1 1 d . . . O1 O 0.18734(17) 0.2377(4) 0.97220(15) 0.0748(10) Uani 1 1 d . . . N2 N 0.15873(19) 0.3574(5) 0.86471(19) 0.0717(12) Uani 1 1 d . . . H2 H 0.1243 0.3830 0.8269 0.086 Uiso 1 1 calc R . . C2A C 0.2352(3) 0.4078(7) 0.8698(2) 0.0768(15) Uani 1 1 d . . . C2B1 C 0.2830(3) 0.2619(8) 0.8637(3) 0.111(2) Uani 1 1 d . . . H2B1 H 0.2840 0.1882 0.9019 0.166 Uiso 1 1 calc R . . H2B2 H 0.3328 0.2964 0.8668 0.166 Uiso 1 1 calc R . . H2B3 H 0.2623 0.2095 0.8186 0.166 Uiso 1 1 calc R . . C2B2 C 0.2313(3) 0.5283(9) 0.8095(3) 0.121(3) Uani 1 1 d . . . H2B4 H 0.2023 0.4837 0.7650 0.182 Uiso 1 1 calc R . . H2B5 H 0.2807 0.5509 0.8065 0.182 Uiso 1 1 calc R . . H2B6 H 0.2085 0.6258 0.8193 0.182 Uiso 1 1 calc R . . C2 C 0.2695(3) 0.4945(6) 0.9413(2) 0.0636(13) Uani 1 1 d . . . O2 O 0.33610(16) 0.4863(4) 0.97038(16) 0.0744(10) Uani 1 1 d . . . N3 N 0.2232(2) 0.5884(4) 0.96626(18) 0.0673(11) Uani 1 1 d D . . H3 H 0.1766 0.5907 0.9439 0.081 Uiso 1 1 calc R . . C3A C 0.2510(3) 0.6870(5) 1.0310(2) 0.0721(14) Uani 1 1 d D . . C3B1 C 0.1825(3) 0.7603(6) 1.0487(3) 0.0854(16) Uani 1 1 d . . . H3B1 H 0.1582 0.6795 1.0695 0.128 Uiso 1 1 calc R . . H3B2 H 0.1485 0.8000 1.0056 0.128 Uiso 1 1 calc R . . H3B3 H 0.1980 0.8471 1.0820 0.128 Uiso 1 1 calc R . . C3B2 C 0.3017(3) 0.8234(7) 1.0171(3) 0.1014(19) Uani 1 1 d . . . H3B4 H 0.3363 0.8545 1.0615 0.152 Uiso 1 1 calc R . . H3B5 H 0.2716 0.9141 0.9966 0.152 Uiso 1 1 calc R . . H3B6 H 0.3285 0.7862 0.9846 0.152 Uiso 1 1 calc R . . C3 C 0.2919(2) 0.5871(6) 1.0947(2) 0.0664(14) Uani 1 1 d . . . O3 O 0.34331(18) 0.6443(4) 1.14186(18) 0.0901(11) Uani 1 1 d . . . N4 N 0.26817(18) 0.4346(4) 1.09807(18) 0.0620(10) Uani 1 1 d . . . H4 H 0.2325 0.3995 1.0633 0.074 Uiso 1 1 calc R . . C4A C 0.3000(2) 0.3268(5) 1.1578(2) 0.0630(13) Uani 1 1 d D . . C4B1 C 0.2614(3) 0.1660(6) 1.1400(3) 0.0845(16) Uani 1 1 d . . . H4B1 H 0.2100 0.1767 1.1393 0.127 Uiso 1 1 calc R . . H4B2 H 0.2851 0.0886 1.1756 0.127 Uiso 1 1 calc R . . H4B3 H 0.2646 0.1309 1.0939 0.127 Uiso 1 1 calc R . . C4B2 C 0.2896(3) 0.3906(8) 1.2283(2) 0.0995(19) Uani 1 1 d D . . H4B4 H 0.3132 0.4937 1.2387 0.149 Uiso 1 1 calc R . . H4B5 H 0.3117 0.3171 1.2663 0.149 Uiso 1 1 calc R . . H4B6 H 0.2374 0.4010 1.2242 0.149 Uiso 1 1 calc R . . C4 C 0.3825(2) 0.2970(6) 1.1651(2) 0.0655(13) Uani 1 1 d . . . O4 O 0.42528(17) 0.2594(4) 1.22322(15) 0.0851(11) Uani 1 1 d . . . N5 N 0.40493(19) 0.3003(5) 1.10526(18) 0.0682(11) Uani 1 1 d D . . H5 H 0.3725 0.3147 1.0647 0.082 Uiso 1 1 calc R . . C5A C 0.4839(2) 0.2799(6) 1.1072(2) 0.0707(14) Uani 1 1 d D . . C5B1 C 0.5259(3) 0.4332(7) 1.1328(3) 0.106(2) Uani 1 1 d . . . H5B1 H 0.5251 0.4547 1.1811 0.159 Uiso 1 1 calc R . . H5B2 H 0.5029 0.5205 1.1025 0.159 Uiso 1 1 calc R . . H5B3 H 0.5766 0.4217 1.1312 0.159 Uiso 1 1 calc R . . C5B2 C 0.4851(3) 0.2418(8) 1.0301(3) 0.103(2) Uani 1 1 d D . . H5B4 H 0.5357 0.2377 1.0277 0.155 Uiso 1 1 calc R . . H5B5 H 0.4588 0.3241 0.9985 0.155 Uiso 1 1 calc R . . H5B6 H 0.4616 0.1400 1.0159 0.155 Uiso 1 1 calc R . . C5 C 0.5167(3) 0.1381(6) 1.1536(3) 0.0732(15) Uani 1 1 d . . . O5 O 0.57659(17) 0.1403(5) 1.1970(2) 0.0967(12) Uani 1 1 d . . . OT O 0.47520(18) 0.0085(4) 1.13635(18) 0.0864(11) Uani 1 1 d . . . CT C 0.5057(4) -0.1403(7) 1.1714(4) 0.126(2) Uani 1 1 d . . . HT1 H 0.5567 -0.1506 1.1709 0.189 Uiso 1 1 calc R . . HT2 H 0.4775 -0.2295 1.1465 0.189 Uiso 1 1 calc R . . HT3 H 0.5029 -0.1392 1.2200 0.189 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 C01 0.084(4) 0.119(5) 0.127(5) -0.008(4) 0.011(4) 0.015(4) C0 0.061(3) 0.099(4) 0.086(4) -0.012(4) 0.016(3) -0.004(3) O0 0.073(2) 0.112(3) 0.096(3) -0.034(2) 0.0082(19) 0.000(2) N1 0.072(3) 0.085(3) 0.073(3) -0.010(3) 0.012(2) -0.004(3) C1A 0.070(3) 0.072(4) 0.066(3) 0.004(3) 0.008(3) -0.001(3) C1B1 0.120(5) 0.081(5) 0.129(5) -0.017(4) 0.004(4) -0.012(4) C1B2 0.098(4) 0.160(6) 0.090(4) 0.029(4) 0.026(4) -0.023(4) C1 0.064(3) 0.060(3) 0.064(3) -0.005(3) 0.005(3) 0.005(3) O1 0.079(2) 0.072(2) 0.065(2) 0.0034(18) 0.0060(17) 0.0011(18) N2 0.067(3) 0.092(3) 0.055(2) 0.009(2) 0.014(2) -0.004(2) C2A 0.067(3) 0.112(4) 0.049(3) -0.004(3) 0.012(2) -0.007(3) C2B1 0.096(4) 0.143(6) 0.095(4) -0.052(4) 0.030(3) 0.014(4) C2B2 0.088(4) 0.206(8) 0.070(4) 0.024(4) 0.023(3) -0.037(5) C2 0.074(3) 0.062(3) 0.051(3) 0.014(3) 0.011(3) -0.001(3) O2 0.055(2) 0.095(3) 0.069(2) 0.0051(18) 0.0097(16) 0.0030(19) N3 0.069(3) 0.064(3) 0.064(3) 0.003(2) 0.010(2) 0.009(2) C3A 0.078(3) 0.057(3) 0.075(3) -0.004(3) 0.012(3) 0.004(3) C3B1 0.082(4) 0.080(4) 0.090(4) -0.002(3) 0.017(3) 0.021(3) C3B2 0.107(4) 0.065(4) 0.121(5) 0.009(3) 0.013(4) -0.018(3) C3 0.058(3) 0.067(4) 0.066(3) -0.010(3) 0.004(2) 0.006(3) O3 0.084(2) 0.081(3) 0.091(3) -0.012(2) 0.0004(19) -0.008(2) N4 0.062(2) 0.057(3) 0.063(2) -0.005(2) 0.0107(19) 0.000(2) C4A 0.068(3) 0.065(3) 0.052(3) 0.004(3) 0.010(2) 0.009(3) C4B1 0.098(4) 0.075(4) 0.081(4) 0.021(3) 0.024(3) -0.003(3) C4B2 0.105(4) 0.138(5) 0.060(3) -0.013(3) 0.029(3) 0.021(4) C4 0.062(3) 0.067(3) 0.061(3) 0.002(3) 0.006(2) 0.007(3) O4 0.076(2) 0.113(3) 0.059(2) 0.013(2) 0.0073(17) 0.016(2) N5 0.069(3) 0.084(3) 0.050(2) 0.005(2) 0.014(2) 0.010(2) C5A 0.059(3) 0.077(4) 0.077(4) 0.005(3) 0.020(3) 0.012(3) C5B1 0.102(4) 0.079(4) 0.141(5) 0.011(4) 0.041(4) -0.010(4) C5B2 0.098(4) 0.127(5) 0.094(4) 0.018(4) 0.043(3) 0.036(4) C5 0.055(3) 0.068(4) 0.094(4) 0.000(3) 0.018(3) 0.006(3) O5 0.060(2) 0.102(3) 0.115(3) 0.009(2) 0.002(2) 0.008(2) OT 0.085(2) 0.061(2) 0.109(3) 0.000(2) 0.022(2) 0.001(2) CT 0.134(6) 0.064(4) 0.190(7) 0.024(4) 0.063(5) 0.015(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 C01 C0 1.499(7) . ? C0 O0 1.223(5) . ? C0 N1 1.346(6) . ? N1 C1A 1.463(6) . ? C1A C1 1.495(6) . ? C1A C1B1 1.537(6) . ? C1A C1B2 1.537(6) . ? C1 O1 1.244(5) . ? C1 N2 1.339(5) . ? N2 C2A 1.466(6) . ? C2A C2B2 1.529(7) . ? C2A C2B1 1.533(7) . ? C2A C2 1.540(7) . ? C2 O2 1.219(5) . ? C2 N3 1.351(5) . ? N3 C3A 1.473(5) . ? C3A C3 1.512(6) . ? C3A C3B1 1.541(7) . ? C3A C3B2 1.549(7) . ? C3 O3 1.227(5) . ? C3 N4 1.352(5) . ? N4 C4A 1.458(5) . ? C4A C4B1 1.515(6) . ? C4A C4 1.528(6) . ? C4A C4B2 1.533(6) . ? C4 O4 1.231(5) . ? C4 N5 1.341(5) . ? N5 C5A 1.475(5) . ? C5A C5 1.510(7) . ? C5A C5B1 1.509(7) . ? C5A C5B2 1.539(6) . ? C5 O5 1.202(5) . ? C5 OT 1.317(5) . ? OT CT 1.453(6) . ? 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 O0 C0 N1 121.2(5) . . ? O0 C0 C01 122.3(5) . . ? N1 C0 C01 116.4(5) . . ? C0 N1 C1A 123.3(4) . . ? N1 C1A C1 111.8(4) . . ? N1 C1A C1B1 107.0(4) . . ? C1 C1A C1B1 107.8(4) . . ? N1 C1A C1B2 108.8(4) . . ? C1 C1A C1B2 111.0(4) . . ? C1B1 C1A C1B2 110.4(5) . . ? O1 C1 N2 120.5(4) . . ? O1 C1 C1A 121.1(4) . . ? N2 C1 C1A 118.4(4) . . ? C1 N2 C2A 123.5(4) . . ? N2 C2A C2B2 107.2(4) . . ? N2 C2A C2B1 110.2(4) . . ? C2B2 C2A C2B1 111.5(5) . . ? N2 C2A C2 110.5(4) . . ? C2B2 C2A C2 107.7(4) . . ? C2B1 C2A C2 109.6(4) . . ? O2 C2 N3 122.6(4) . . ? O2 C2 C2A 120.7(4) . . ? N3 C2 C2A 116.6(4) . . ? C2 N3 C3A 121.3(4) . . ? N3 C3A C3 111.9(4) . . ? N3 C3A C3B1 107.0(4) . . ? C3 C3A C3B1 107.4(4) . . ? N3 C3A C3B2 110.4(4) . . ? C3 C3A C3B2 110.6(4) . . ? C3B1 C3A C3B2 109.5(4) . . ? O3 C3 N4 121.8(4) . . ? O3 C3 C3A 120.9(4) . . ? N4 C3 C3A 117.2(4) . . ? C3 N4 C4A 123.3(4) . . ? N4 C4A C4B1 107.4(3) . . ? N4 C4A C4 110.8(4) . . ? C4B1 C4A C4 106.4(4) . . ? N4 C4A C4B2 112.0(4) . . ? C4B1 C4A C4B2 109.8(4) . . ? C4 C4A C4B2 110.3(4) . . ? O4 C4 N5 121.5(4) . . ? O4 C4 C4A 120.7(4) . . ? N5 C4 C4A 117.6(4) . . ? C4 N5 C5A 121.7(4) . . ? N5 C5A C5 110.1(4) . . ? N5 C5A C5B1 109.7(4) . . ? C5 C5A C5B1 112.0(4) . . ? N5 C5A C5B2 106.4(4) . . ? C5 C5A C5B2 108.0(4) . . ? C5B1 C5A C5B2 110.5(5) . . ? O5 C5 OT 124.1(5) . . ? O5 C5 C5A 123.6(5) . . ? OT C5 C5A 112.0(4) . . ? C5 OT CT 116.9(4) . . ? 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 O0 C0 N1 C1A 9.8(7) . . . . ? C01 C0 N1 C1A -168.0(5) . . . . y C0 N1 C1A C1 -56.8(6) . . . . y C0 N1 C1A C1B1 -174.5(5) . . . . ? C0 N1 C1A C1B2 66.1(6) . . . . ? N1 C1A C1 O1 147.2(4) . . . . ? C1B1 C1A C1 O1 -95.4(5) . . . . ? C1B2 C1A C1 O1 25.6(6) . . . . ? N1 C1A C1 N2 -33.6(6) . . . . y C1B1 C1A C1 N2 83.8(5) . . . . ? C1B2 C1A C1 N2 -155.2(5) . . . . ? O1 C1 N2 C2A 1.9(7) . . . . ? C1A C1 N2 C2A -177.2(4) . . . . y C1 N2 C2A C2B2 -168.4(5) . . . . ? C1 N2 C2A C2B1 70.1(6) . . . . ? C1 N2 C2A C2 -51.2(6) . . . . y N2 C2A C2 O2 148.7(4) . . . . ? C2B2 C2A C2 O2 -94.4(5) . . . . ? C2B1 C2A C2 O2 27.0(6) . . . . ? N2 C2A C2 N3 -36.4(6) . . . . y C2B2 C2A C2 N3 80.5(5) . . . . ? C2B1 C2A C2 N3 -158.0(4) . . . . ? O2 C2 N3 C3A -0.3(7) . . . . ? C2A C2 N3 C3A -175.1(4) . . . . y C2 N3 C3A C3 -55.7(6) . . . . y C2 N3 C3A C3B1 -173.0(4) . . . . ? C2 N3 C3A C3B2 67.9(5) . . . . ? N3 C3A C3 O3 149.1(4) . . . . ? C3B1 C3A C3 O3 -93.8(5) . . . . ? C3B2 C3A C3 O3 25.6(6) . . . . ? N3 C3A C3 N4 -32.5(6) . . . . y C3B1 C3A C3 N4 84.6(5) . . . . ? C3B2 C3A C3 N4 -156.0(4) . . . . ? O3 C3 N4 C4A 1.1(7) . . . . ? C3A C3 N4 C4A -177.2(4) . . . . y C3 N4 C4A C4B1 -177.3(4) . . . . ? C3 N4 C4A C4 -61.4(5) . . . . y C3 N4 C4A C4B2 62.1(6) . . . . ? N4 C4A C4 O4 154.4(4) . . . . ? C4B1 C4A C4 O4 -89.2(5) . . . . ? C4B2 C4A C4 O4 29.9(6) . . . . ? N4 C4A C4 N5 -30.9(6) . . . . y C4B1 C4A C4 N5 85.5(5) . . . . ? C4B2 C4A C4 N5 -155.4(4) . . . . ? O4 C4 N5 C5A -8.1(7) . . . . ? C4A C4 N5 C5A 177.3(4) . . . . y C4 N5 C5A C5 47.2(6) . . . . y C4 N5 C5A C5B1 -76.5(6) . . . . ? C4 N5 C5A C5B2 164.0(5) . . . . ? N5 C5A C5 O5 -135.4(5) . . . . ? C5B1 C5A C5 O5 -13.0(7) . . . . ? C5B2 C5A C5 O5 108.8(6) . . . . ? N5 C5A C5 OT 50.3(5) . . . . y C5B1 C5A C5 OT 172.7(4) . . . . ? C5B2 C5A C5 OT -65.4(5) . . . . ? O5 C5 OT CT -1.5(7) . . . . ? C5A C5 OT CT 172.7(4) . . . . y 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 N3 H3 O0 0.86 2.22 3.029(5) 156.2 . N4 H4 O1 0.86 2.20 2.987(5) 152.1 . N5 H5 O2 0.86 2.28 3.012(5) 143.5 . N1 H1 O4 0.86 1.97 2.817(5) 168.4 4_565 N2 H2 O5 0.86 2.44 3.198(5) 146.9 4_565 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 60.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.382 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.071 #===END===