Electronic Supplementary Material for CrystEngComm This Journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'A. Nangia' _publ_contact_author_address ; School of Chemistry University of Hyderabad P O Central University 500046 Hyderabad INDIA ; _publ_contact_author_email 'ASHWINI NANGIA@REDIFFMAIL.COM' _publ_section_title ; Water mediated nanotube in tetrapeptide cyclo(Phe-Pro-Leu-Aha) trihydrate and crystal structure of cyclo(D-Phe-Pro-Leu-Aha) anhydrate ; loop_ _publ_author_name 'A. Nangia' 'N. Jagadeesh Babu' 'Javed Iqbal' 'B. M. Rajesh' # Attachment '2.cif' data___BMR_161_JMB _database_code_depnum_ccdc_archive 'CCDC 258298' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C26 H38 N4 O4 ' _chemical_formula_moiety 'C26 H38 N4 O4 ' _chemical_formula_weight 470.61 _chemical_melting_point ? _chemical_absolute_configuration syn #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 #------------------------------------------------------------------------------ _cell_length_a 11.292(6) _cell_length_b 15.112(10) _cell_length_c 15.805(12) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2696.9(30) _cell_formula_units_Z 4 _cell_measurement_reflns_used 338 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 26.4 _cell_measurement_temperature 298.1 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.159 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016.00 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.980 _exptl_absorpt_correction_T_max 0.984 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 32348 _diffrn_reflns_av_R_equivalents 0.041 _diffrn_reflns_theta_max 26.36 _diffrn_measured_fraction_theta_max 0.9885 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.9885 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 17 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 1.2 sigma(F^2^). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3091 _reflns_number_gt 2528 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0820 _refine_ls_wR_factor_ref 0.0970 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 2740 _refine_ls_number_parameters 336 _refine_ls_goodness_of_fit_ref 1.133 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979) 6.6463 0.9035 4.5514 ; _refine_ls_shift/su_max 0.0100 _refine_diff_density_max 0.70 _refine_diff_density_min -0.44 _refine_ls_extinction_method 'Larson (1970) Crystallographic Computing eq. 22' _refine_ls_extinction_coef 594.0(20) _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O1 O Uani -0.1003(3) 0.3371(2) 0.6233(2) 1.000 0.0590(12) . . O2 O Uani 0.1443(3) 0.2547(2) 0.5774(2) 1.000 0.0513(10) . . O3 O Uani 0.2213(4) 0.4573(2) 0.4298(2) 1.000 0.0720(12) . . O4 O Uani 0.1283(5) 0.5733(3) 0.6992(2) 1.000 0.0867(16) . . N1 N Uani 0.1643(4) 0.4301(3) 0.6703(3) 1.000 0.0620(14) . . N2 N Uani -0.0663(4) 0.1970(2) 0.6624(2) 1.000 0.0530(12) . . N3 N Uani 0.0301(3) 0.2668(2) 0.4615(2) 1.000 0.0460(12) . . N4 N Uani 0.0611(4) 0.4406(3) 0.5148(2) 1.000 0.0503(12) . . C1 C Uani 0.2211(6) 0.4068(4) 0.7493(3) 1.000 0.0723(19) . . C2 C Uani 0.1589(8) 0.3243(4) 0.7901(4) 1.000 0.090(2) . . C3 C Uani 0.0578(7) 0.3419(5) 0.8479(4) 1.000 0.091(2) . . C4 C Uani -0.0541(6) 0.3730(4) 0.8083(3) 1.000 0.0743(19) . . C5 C Uani -0.1329(5) 0.3012(3) 0.7682(3) 1.000 0.0637(16) . . C6 C Uani -0.0985(4) 0.2801(3) 0.6791(3) 1.000 0.0520(12) . . C7 C Uani -0.0353(4) 0.1699(3) 0.5766(3) 1.000 0.0483(12) . . C8 C Uani 0.0214(5) 0.0777(3) 0.5802(3) 1.000 0.0583(14) . . C9 C Uani 0.0437(5) 0.0425(3) 0.4922(3) 1.000 0.0590(16) . . C10 C Uani -0.0446(5) -0.0051(4) 0.4506(4) 1.000 0.0717(17) . . C11 C Uani -0.0300(7) -0.0324(5) 0.3691(4) 1.000 0.098(3) . . C12 C Uani 0.0740(8) -0.0138(5) 0.3272(4) 1.000 0.101(3) . . C13 C Uani 0.1623(6) 0.0339(4) 0.3658(4) 1.000 0.086(2) . . C14 C Uani 0.1464(5) 0.0611(3) 0.4491(4) 1.000 0.0660(17) . . C15 C Uani 0.0514(4) 0.2349(3) 0.5395(2) 1.000 0.0433(12) . . C16 C Uani 0.1191(4) 0.3210(3) 0.4184(3) 1.000 0.0510(12) . . C17 C Uani 0.0747(6) 0.3252(5) 0.3273(3) 1.000 0.076(2) . . C18 C Uiso -0.0547(8) 0.3112(6) 0.3364(6) 1.000 0.106(2) . . C19 C Uani -0.0719(5) 0.2476(4) 0.4064(3) 1.000 0.0660(16) . . C20 C Uani 0.1385(4) 0.4121(3) 0.4559(3) 1.000 0.0500(14) . . C21 C Uani 0.0764(4) 0.5230(3) 0.5609(3) 1.000 0.0547(14) . . C22 C Uani -0.0367(6) 0.5775(4) 0.5610(4) 1.000 0.0740(19) . . C23 C Uiso -0.0856(7) 0.6069(5) 0.4768(5) 1.000 0.099(2) . . C24 C Uiso 0.009(2) 0.6662(13) 0.4354(13) 0.600 0.129(6) . . C25 C Uiso -0.2060(10) 0.6567(8) 0.4960(8) 0.600 0.085(3) . . C26 C Uani 0.1249(4) 0.5099(3) 0.6498(3) 1.000 0.0557(14) . . C27 C Uiso -0.175(2) 0.6767(12) 0.4680(10) 0.400 0.095(6) . . C28 C Uiso -0.003(2) 0.633(2) 0.410(2) 0.400 0.131(9) . . H3 H Uiso -0.0346(6) 0.4144(4) 0.7653(3) 1.000 0.089(2) calc . H4 H Uiso -0.0994(6) 0.4015(4) 0.8510(3) 1.000 0.089(2) calc . H5 H Uiso 0.0411(7) 0.2887(5) 0.8777(4) 1.000 0.109(2) calc . H6 H Uiso 0.0824(7) 0.3861(5) 0.8868(4) 1.000 0.109(2) calc . H7 H Uiso 0.2170(8) 0.2929(4) 0.8215(4) 1.000 0.108(3) calc . H8 H Uiso 0.1306(8) 0.2880(4) 0.7453(4) 1.000 0.108(3) calc . H9 H Uiso 0.2161(6) 0.4554(4) 0.7873(3) 1.000 0.087(2) calc . H10 H Uiso 0.3020(6) 0.3933(4) 0.7388(3) 1.000 0.087(2) calc . H11 H Uiso 0.163(5) 0.392(3) 0.634(3) 1.000 0.053(13) calc . H12 H Uiso 0.1335(4) 0.5568(3) 0.5307(3) 1.000 0.065(2) calc . H13 H Uiso -0.0964(6) 0.5427(4) 0.5872(4) 1.000 0.089(2) calc . H14 H Uiso -0.0226(6) 0.6290(4) 0.5940(4) 1.000 0.089(2) calc . H16 H Uiso 0.021(4) 0.408(3) 0.529(3) 1.000 0.030(11) calc . H23 H Uiso 0.1925(4) 0.2902(3) 0.4189(3) 1.000 0.061(2) calc . H24 H Uiso 0.0905(6) 0.3815(5) 0.3029(3) 1.000 0.092(2) calc . H25 H Uiso 0.1097(6) 0.2803(5) 0.2935(3) 1.000 0.092(2) calc . H26 H Uiso -0.0864(8) 0.2877(6) 0.2854(6) 1.000 0.127(3) calc . H27 H Uiso -0.0930(8) 0.3655(6) 0.3493(6) 1.000 0.127(3) calc . H28 H Uiso -0.0697(5) 0.1883(4) 0.3865(3) 1.000 0.079(2) calc . H29 H Uiso -0.1448(5) 0.2578(4) 0.4349(3) 1.000 0.079(2) calc . H30 H Uiso -0.1047(4) 0.1679(3) 0.5427(3) 1.000 0.058(2) calc . H31 H Uiso -0.0298(5) 0.0382(3) 0.6094(3) 1.000 0.070(2) calc . H32 H Uiso 0.0947(5) 0.0816(3) 0.6095(3) 1.000 0.070(2) calc . H33 H Uiso 0.2082(5) 0.0924(3) 0.4769(4) 1.000 0.079(2) calc . H34 H Uiso 0.2331(6) 0.0476(4) 0.3361(4) 1.000 0.103(2) calc . H35 H Uiso 0.0835(8) -0.0326(5) 0.2702(4) 1.000 0.121(3) calc . H36 H Uiso -0.0908(7) -0.0649(5) 0.3416(4) 1.000 0.117(3) calc . H37 H Uiso -0.1161(5) -0.0189(4) 0.4794(4) 1.000 0.086(2) calc . H38 H Uiso -0.068(4) 0.155(3) 0.704(3) 1.000 0.041(10) calc . H1 H Uiso -0.2128(5) 0.3211(3) 0.7688(3) 1.000 0.077(2) calc . H2 H Uiso -0.1262(5) 0.2489(3) 0.8011(3) 1.000 0.076(2) calc . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.069(2) 0.052(2) 0.056(2) 0.0040(10) 0.010(2) 0.008(2) O2 0.055(2) 0.054(2) 0.0450(10) -0.0054(13) -0.0076(13) 0.0019(13) O3 0.081(2) 0.063(2) 0.072(2) 0.001(2) 0.022(2) -0.015(2) O4 0.133(4) 0.062(2) 0.065(2) -0.023(2) -0.015(2) 0.014(2) N1 0.083(3) 0.056(2) 0.047(2) -0.007(2) -0.007(2) 0.003(2) N2 0.073(2) 0.044(2) 0.042(2) 0.003(2) 0.007(2) 0.000(2) N3 0.056(2) 0.043(2) 0.039(2) -0.0022(13) -0.0030(10) -0.0010(10) N4 0.060(2) 0.041(2) 0.050(2) 0.001(2) 0.007(2) -0.006(2) C1 0.084(4) 0.079(3) 0.054(3) 0.000(2) -0.012(3) 0.012(3) C2 0.137(6) 0.072(3) 0.061(3) 0.004(3) -0.013(4) 0.021(4) C3 0.121(5) 0.082(4) 0.070(3) 0.003(3) -0.005(4) -0.007(4) C4 0.105(4) 0.061(3) 0.057(3) -0.009(2) 0.018(3) -0.012(3) C5 0.082(3) 0.054(2) 0.055(3) -0.008(2) 0.019(3) -0.003(3) C6 0.058(2) 0.048(2) 0.050(2) -0.003(2) 0.008(2) -0.003(2) C7 0.061(2) 0.043(2) 0.041(2) -0.004(2) -0.003(2) -0.004(2) C8 0.080(3) 0.044(2) 0.051(2) 0.000(2) 0.003(2) 0.005(2) C9 0.074(3) 0.040(2) 0.063(3) -0.007(2) -0.005(3) 0.006(2) C10 0.073(3) 0.067(3) 0.075(3) -0.017(3) 0.003(3) -0.013(3) C11 0.114(5) 0.096(4) 0.083(4) -0.037(4) 0.001(4) -0.027(4) C12 0.134(6) 0.102(5) 0.066(3) -0.034(3) 0.014(4) -0.024(5) C13 0.088(4) 0.084(4) 0.085(4) -0.019(3) 0.016(3) -0.010(3) C14 0.067(3) 0.055(3) 0.076(3) -0.013(2) 0.000(3) 0.001(2) C15 0.050(2) 0.042(2) 0.038(2) -0.009(2) -0.006(2) 0.005(2) C16 0.057(2) 0.055(2) 0.041(2) 0.000(2) 0.000(2) 0.002(2) C17 0.094(4) 0.091(4) 0.044(2) -0.001(2) 0.004(3) -0.009(3) C19 0.072(3) 0.071(3) 0.055(2) 0.005(2) -0.019(2) -0.012(3) C20 0.059(3) 0.049(2) 0.042(2) 0.006(2) -0.001(2) 0.002(2) C21 0.066(3) 0.043(2) 0.055(2) -0.003(2) 0.001(2) -0.005(2) C22 0.091(4) 0.055(3) 0.076(3) -0.009(2) -0.009(3) 0.011(3) C26 0.066(3) 0.050(2) 0.051(2) -0.006(2) 0.005(2) -0.002(2) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.233(6) . . yes O2 C15 1.245(5) . . yes O3 C20 1.229(6) . . yes O4 C26 1.237(6) . . yes N1 C1 1.447(7) . . yes N1 C26 1.326(7) . . yes N2 C6 1.334(6) . . yes N2 C7 1.459(6) . . yes N3 C15 1.345(5) . . yes N3 C16 1.465(6) . . yes N3 C19 1.473(6) . . yes N4 C20 1.348(6) . . yes N4 C21 1.453(6) . . yes N1 H11 0.81(5) . . no N2 H38 0.91(5) . . no N4 H16 0.71(5) . . no C1 C2 1.570(9) . . no C2 C3 1.486(11) . . no C3 C4 1.486(10) . . no C4 C5 1.540(8) . . no C5 C6 1.495(7) . . no C7 C15 1.506(6) . . no C7 C8 1.534(7) . . no C8 C9 1.510(7) . . no C9 C10 1.394(8) . . no C9 C14 1.374(8) . . no C10 C11 1.363(9) . . no C11 C12 1.377(11) . . no C12 C13 1.373(10) . . no C13 C14 1.391(9) . . no C16 C17 1.526(7) . . no C16 C20 1.515(7) . . no C17 C18 1.483(11) . . no C18 C19 1.478(11) . . no C21 C22 1.520(8) . . no C21 C26 1.521(7) . . no C22 C23 1.508(10) . . no C23 C24 1.54(2) . . no C23 C25 1.583(14) . . no C23 C27 1.47(2) . . no C23 C28 1.46(3) . . no C1 H9 0.950(8) . . no C1 H10 0.951(9) . . no C2 H7 0.950(11) . . no C2 H8 0.951(9) . . no C3 H5 0.951(10) . . no C3 H6 0.949(10) . . no C4 H3 0.950(8) . . no C4 H4 0.950(8) . . no C5 H1 0.951(8) . . no C5 H2 0.949(7) . . no C7 H30 0.950(7) . . no C8 H31 0.951(7) . . no C8 H32 0.950(8) . . no C10 H37 0.950(8) . . no C11 H36 0.950(11) . . no C12 H35 0.951(9) . . no C13 H34 0.950(9) . . no C14 H33 0.951(8) . . no C16 H23 0.951(6) . . no C17 H24 0.951(10) . . no C17 H25 0.950(9) . . no C18 H26 0.951(13) . . no C18 H27 0.950(13) . . no C19 H28 0.950(8) . . no C19 H29 0.951(8) . . no C21 H12 0.951(7) . . no C22 H13 0.950(9) . . no C22 H14 0.950(9) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C26 125.5(5) . . . yes C6 N2 C7 120.9(4) . . . yes C15 N3 C16 120.3(4) . . . yes C15 N3 C19 127.7(4) . . . yes C16 N3 C19 111.8(3) . . . yes C20 N4 C21 122.9(4) . . . yes C26 N1 H11 118(4) . . . no C1 N1 H11 116(4) . . . no C7 N2 H38 119(3) . . . no C6 N2 H38 120(3) . . . no C20 N4 H16 114(4) . . . no C21 N4 H16 121(4) . . . no N1 C1 C2 110.5(5) . . . yes C1 C2 C3 117.0(5) . . . no C2 C3 C4 116.8(5) . . . no C3 C4 C5 116.2(5) . . . no C4 C5 C6 112.8(4) . . . no O1 C6 C5 121.4(4) . . . yes O1 C6 N2 121.4(4) . . . yes N2 C6 C5 117.3(4) . . . yes N2 C7 C15 109.6(4) . . . yes N2 C7 C8 108.7(4) . . . yes C8 C7 C15 109.6(4) . . . no C7 C8 C9 110.8(4) . . . no C8 C9 C14 121.7(5) . . . no C8 C9 C10 119.8(5) . . . no C10 C9 C14 118.4(5) . . . no C9 C10 C11 121.0(6) . . . no C10 C11 C12 119.7(7) . . . no C11 C12 C13 120.8(6) . . . no C12 C13 C14 118.8(6) . . . no C9 C14 C13 121.2(5) . . . no N3 C15 C7 118.3(4) . . . yes O2 C15 C7 121.2(3) . . . yes O2 C15 N3 120.4(4) . . . yes C17 C16 C20 112.3(4) . . . no N3 C16 C17 103.7(4) . . . yes N3 C16 C20 115.2(4) . . . yes C16 C17 C18 103.1(5) . . . no C17 C18 C19 107.1(7) . . . no N3 C19 C18 102.2(5) . . . yes O3 C20 N4 123.2(4) . . . yes N4 C20 C16 117.8(4) . . . yes O3 C20 C16 118.9(4) . . . yes N4 C21 C22 111.4(4) . . . yes C22 C21 C26 111.9(4) . . . no N4 C21 C26 113.2(4) . . . yes C21 C22 C23 117.8(5) . . . no C22 C23 C25 106.6(7) . . . no C22 C23 C24 107.0(10) . . . no C24 C23 C25 113.6(10) . . . no C22 C23 C27 123.2(9) . . . no C22 C23 C28 118.9(12) . . . no C27 C23 C28 100.2(14) . . . no N1 C26 C21 117.7(4) . . . yes O4 C26 N1 122.7(5) . . . yes O4 C26 C21 119.6(4) . . . yes N1 C1 H9 109.3(6) . . . no N1 C1 H10 109.1(5) . . . no C2 C1 H9 109.1(6) . . . no C2 C1 H10 109.4(7) . . . no H9 C1 H10 109.5(8) . . . no C1 C2 H7 107.6(9) . . . no C1 C2 H8 107.6(7) . . . no C3 C2 H7 107.4(7) . . . no C3 C2 H8 107.6(9) . . . no H7 C2 H8 109.5(9) . . . no C2 C3 H5 107.8(8) . . . no C2 C3 H6 107.4(8) . . . no C4 C3 H5 107.9(8) . . . no C4 C3 H6 107.4(8) . . . no H5 C3 H6 109.4(9) . . . no C3 C4 H3 108.2(7) . . . no C3 C4 H4 107.6(6) . . . no C5 C4 H3 107.7(6) . . . no C5 C4 H4 107.5(7) . . . no H3 C4 H4 109.6(8) . . . no C4 C5 H1 108.7(5) . . . no C4 C5 H2 108.4(6) . . . no C6 C5 H1 108.9(5) . . . no C6 C5 H2 108.5(5) . . . no H1 C5 H2 109.5(7) . . . no N2 C7 H30 109.6(5) . . . no C8 C7 H30 109.7(5) . . . no C15 C7 H30 109.7(5) . . . no C7 C8 H31 109.5(6) . . . no C7 C8 H32 109.0(5) . . . no C9 C8 H31 109.1(5) . . . no C9 C8 H32 109.0(6) . . . no H31 C8 H32 109.4(6) . . . no C9 C10 H37 119.7(7) . . . no C11 C10 H37 119.3(7) . . . no C10 C11 H36 120.1(8) . . . no C12 C11 H36 120.1(8) . . . no C11 C12 H35 119.4(10) . . . no C13 C12 H35 119.7(10) . . . no C12 C13 H34 120.4(7) . . . no C14 C13 H34 120.8(7) . . . no C9 C14 H33 119.5(7) . . . no C13 C14 H33 119.3(7) . . . no N3 C16 H23 108.7(5) . . . no C17 C16 H23 108.3(5) . . . no C20 C16 H23 108.4(5) . . . no C16 C17 H24 111.0(6) . . . no C16 C17 H25 111.4(7) . . . no C18 C17 H24 110.6(8) . . . no C18 C17 H25 111.3(8) . . . no H24 C17 H25 109.5(8) . . . no C17 C18 H26 110.0(10) . . . no C17 C18 H27 110.3(10) . . . no C19 C18 H26 110.0(10) . . . no C19 C18 H27 110.0(10) . . . no H26 C18 H27 109.5(12) . . . no N3 C19 H28 111.2(6) . . . no N3 C19 H29 111.4(5) . . . no C18 C19 H28 111.2(6) . . . no C18 C19 H29 111.3(7) . . . no H28 C19 H29 109.4(8) . . . no N4 C21 H12 106.8(5) . . . no C22 C21 H12 106.2(5) . . . no C26 C21 H12 106.8(5) . . . no C21 C22 H13 107.3(6) . . . no C21 C22 H14 107.7(7) . . . no C23 C22 H13 106.7(7) . . . no C23 C22 H14 107.7(7) . . . no H13 C22 H14 109.5(8) . . . no 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 C26 N1 C1 C2 128.0(6) . . . . no C1 N1 C26 O4 -3.4(8) . . . . no C1 N1 C26 C21 175.3(5) . . . . no C7 N2 C6 O1 -1.8(7) . . . . no C7 N2 C6 C5 177.9(4) . . . . no C6 N2 C7 C8 168.6(4) . . . . no C6 N2 C7 C15 48.9(6) . . . . no C16 N3 C15 O2 3.6(6) . . . . no C16 N3 C15 C7 -172.1(4) . . . . no C19 N3 C15 O2 177.3(4) . . . . no C19 N3 C15 C7 1.7(6) . . . . no C15 N3 C16 C17 167.4(4) . . . . no C15 N3 C16 C20 -69.6(5) . . . . no C19 N3 C16 C17 -7.3(5) . . . . no C19 N3 C16 C20 115.8(4) . . . . no C15 N3 C19 C18 171.9(5) . . . . no C16 N3 C19 C18 -14.0(6) . . . . no C21 N4 C20 O3 -8.0(7) . . . . no C21 N4 C20 C16 174.2(4) . . . . no C20 N4 C21 C22 131.8(5) . . . . no C20 N4 C21 C26 -101.1(5) . . . . no N1 C1 C2 C3 -89.2(7) . . . . no C1 C2 C3 C4 71.8(8) . . . . no C2 C3 C4 C5 80.3(7) . . . . no C3 C4 C5 C6 -85.6(6) . . . . no C4 C5 C6 O1 -60.3(6) . . . . no C4 C5 C6 N2 120.0(5) . . . . no N2 C7 C8 C9 174.2(4) . . . . no N2 C7 C15 O2 53.0(5) . . . . no N2 C7 C15 N3 -131.5(4) . . . . no C8 C7 C15 O2 -66.2(5) . . . . no C8 C7 C15 N3 109.4(4) . . . . no C15 C7 C8 C9 -66.1(5) . . . . no C7 C8 C9 C10 -88.3(6) . . . . no C7 C8 C9 C14 87.2(6) . . . . no C8 C9 C14 C13 -175.2(5) . . . . no C10 C9 C14 C13 0.4(8) . . . . no C8 C9 C10 C11 175.5(6) . . . . no C14 C9 C10 C11 -0.2(8) . . . . no C9 C10 C11 C12 0.8(10) . . . . no C10 C11 C12 C13 -1.6(11) . . . . no C11 C12 C13 C14 1.8(10) . . . . no C12 C13 C14 C9 -1.2(9) . . . . no C20 C16 C17 C18 -99.5(6) . . . . no N3 C16 C20 O3 171.3(4) . . . . no N3 C16 C20 N4 -10.7(6) . . . . no C17 C16 C20 O3 -70.3(6) . . . . no C17 C16 C20 N4 107.7(5) . . . . no N3 C16 C17 C18 25.5(6) . . . . no C16 C17 C18 C19 -35.6(8) . . . . no C17 C18 C19 N3 30.7(7) . . . . no N4 C21 C26 N1 10.2(6) . . . . no C22 C21 C26 O4 -44.3(6) . . . . no N4 C21 C26 O4 -171.1(5) . . . . no N4 C21 C22 C23 -60.6(7) . . . . no C26 C21 C22 C23 171.5(5) . . . . no C22 C21 C26 N1 137.1(5) . . . . no C21 C22 C23 C24 -61.4(10) . . . . no C21 C22 C23 C25 176.7(6) . . . . no #===END data_an630_m _database_code_depnum_ccdc_archive 'CCDC 652110' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common cyclo(Phe-Pro-Leu-Aha) _chemical_melting_point ? _chemical_formula_moiety 'C26 H38 N4 O4, 3(H2 O)' _chemical_formula_sum 'C26 H44 N4 O7' _chemical_formula_weight 524.65 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.4493(16) _cell_length_b 14.125(2) _cell_length_c 21.736(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2901.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 7206 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 23.06 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.201 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9552 _exptl_absorpt_correction_T_max 0.9828 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21171 _diffrn_reflns_av_R_equivalents 0.0384 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3176 _reflns_number_gt 2742 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0708P)^2^+1.0583P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _chemical_absolute_configuration rmad _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 3176 _refine_ls_number_parameters 376 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0768 _refine_ls_R_factor_gt 0.0665 _refine_ls_wR_factor_ref 0.1596 _refine_ls_wR_factor_gt 0.1537 _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_restrained_S_all 1.149 _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 O3 O 0.5939(3) 0.2339(2) 0.76237(15) 0.0580(8) Uani 1 1 d . . . O1 O 0.1406(4) 0.0348(2) 0.78315(16) 0.0653(9) Uani 1 1 d . . . N4 N 0.4344(4) 0.0568(3) 0.59734(17) 0.0551(9) Uani 1 1 d . . . O4 O 0.6292(4) -0.0321(2) 0.61331(17) 0.0688(9) Uani 1 1 d . . . C10 C 0.5457(4) -0.0451(3) 0.84467(17) 0.0412(9) Uani 1 1 d . . . O2 O 0.5536(3) -0.12914(19) 0.85672(15) 0.0575(8) Uani 1 1 d . . . N1 N 0.3200(4) -0.0662(3) 0.79692(17) 0.0468(9) Uani 1 1 d . . . N2 N 0.6599(3) 0.0109(2) 0.84039(15) 0.0414(8) Uani 1 1 d . . . N3 N 0.6370(4) 0.0901(2) 0.72162(15) 0.0461(8) Uani 1 1 d . . . C15 C 0.6256(4) 0.1507(3) 0.76836(19) 0.0423(9) Uani 1 1 d . . . C16 C 0.6247(5) 0.1226(3) 0.65781(19) 0.0495(10) Uani 1 1 d . . . H16 H 0.5592 0.1763 0.6564 0.059 Uiso 1 1 calc R . . C2 C 0.3993(4) -0.0027(3) 0.83627(19) 0.0425(9) Uani 1 1 d . . . H2 H 0.4069 0.0597 0.8168 0.051 Uiso 1 1 calc R . . C11 C 0.6614(4) 0.1142(3) 0.83234(18) 0.0420(9) Uani 1 1 d . . . H11 H 0.5967 0.1430 0.8622 0.050 Uiso 1 1 calc R . . C1 C 0.1953(4) -0.0431(3) 0.7727(2) 0.0478(10) Uani 1 1 d . . . C9 C 0.5035(5) 0.0615(4) 0.9805(2) 0.0565(12) Uani 1 1 d . . . H9 H 0.5287 -0.0013 0.9871 0.068 Uiso 1 1 calc R . . C4 C 0.3974(4) 0.0832(3) 0.93858(18) 0.0451(10) Uani 1 1 d . . . C21 C 0.5622(5) 0.0413(3) 0.62046(19) 0.0509(10) Uani 1 1 d . . . C26 C 0.1241(5) -0.1166(3) 0.7335(2) 0.0551(11) Uani 1 1 d . . . H26A H 0.0552 -0.1504 0.7583 0.066 Uiso 1 1 calc R . . H26B H 0.1944 -0.1620 0.7198 0.066 Uiso 1 1 calc R . . C5 C 0.3624(5) 0.1768(3) 0.9303(2) 0.0573(11) Uani 1 1 d . . . H5 H 0.2908 0.1921 0.9027 0.069 Uiso 1 1 calc R . . O6 O 0.3376(6) 0.3498(4) 0.7868(2) 0.0959(14) Uani 1 1 d . . . C13 C 0.8707(5) 0.0610(4) 0.8874(2) 0.0669(13) Uani 1 1 d . . . H13A H 0.8433 0.0681 0.9302 0.080 Uiso 1 1 calc R . . H13B H 0.9730 0.0566 0.8849 0.080 Uiso 1 1 calc R . . C3 C 0.3293(5) 0.0070(3) 0.9002(2) 0.0550(11) Uani 1 1 d . . . H3A H 0.2297 0.0215 0.8949 0.066 Uiso 1 1 calc R . . H3B H 0.3362 -0.0530 0.9217 0.066 Uiso 1 1 calc R . . C22 C 0.3560(6) -0.0145(3) 0.5632(2) 0.0639(12) Uani 1 1 d . . . H22A H 0.4224 -0.0548 0.5414 0.077 Uiso 1 1 calc R . . H22B H 0.2970 0.0166 0.5328 0.077 Uiso 1 1 calc R . . C25 C 0.0502(5) -0.0753(4) 0.6778(2) 0.0640(13) Uani 1 1 d . . . H25A H 0.0087 -0.1266 0.6542 0.077 Uiso 1 1 calc R . . H25B H -0.0262 -0.0348 0.6916 0.077 Uiso 1 1 calc R . . C12 C 0.8153(5) 0.1418(4) 0.8488(2) 0.0595(12) Uani 1 1 d . . . H12A H 0.8717 0.1495 0.8119 0.071 Uiso 1 1 calc R . . H12B H 0.8172 0.2006 0.8719 0.071 Uiso 1 1 calc R . . C17 C 0.7691(5) 0.1548(4) 0.6345(2) 0.0597(12) Uani 1 1 d . B . H17A H 0.8157 0.1902 0.6669 0.072 Uiso 1 1 calc R . . H17B H 0.8262 0.0992 0.6261 0.072 Uiso 1 1 calc R . . C24 C 0.1461(5) -0.0189(3) 0.6362(2) 0.0617(12) Uani 1 1 d . . . H24A H 0.1900 0.0308 0.6604 0.074 Uiso 1 1 calc R . . H24B H 0.0886 0.0114 0.6050 0.074 Uiso 1 1 calc R . . C8 C 0.5723(5) 0.1332(5) 1.0125(2) 0.0713(15) Uani 1 1 d . . . H8 H 0.6435 0.1187 1.0405 0.086 Uiso 1 1 calc R . . C7 C 0.5340(6) 0.2262(4) 1.0024(3) 0.0754(16) Uani 1 1 d . . . H7 H 0.5798 0.2742 1.0239 0.090 Uiso 1 1 calc R . . C14 C 0.8004(5) -0.0248(3) 0.8586(3) 0.0596(12) Uani 1 1 d . . . H14A H 0.8532 -0.0468 0.8231 0.072 Uiso 1 1 calc R . . H14B H 0.7921 -0.0761 0.8880 0.072 Uiso 1 1 calc R . . C23 C 0.2634(5) -0.0756(3) 0.6040(2) 0.0604(12) Uani 1 1 d . . . H23A H 0.3221 -0.1057 0.6349 0.073 Uiso 1 1 calc R . . H23B H 0.2205 -0.1250 0.5793 0.073 Uiso 1 1 calc R . . C6 C 0.4303(6) 0.2489(4) 0.9616(3) 0.0745(15) Uani 1 1 d . . . H6 H 0.4055 0.3117 0.9548 0.089 Uiso 1 1 calc R . . C18 C 0.7646(7) 0.2156(5) 0.5771(3) 0.0914(19) Uani 1 1 d . . . H18 H 0.6911 0.2639 0.5823 0.110 Uiso 1 1 calc R A 1 O5 O 0.7305(5) 0.7173(3) 0.8740(2) 0.0802(12) Uani 1 1 d . . . O7 O 0.8717(6) 0.7204(4) 0.7613(3) 0.1021(16) Uani 1 1 d . . . C20 C 0.7338(11) 0.1631(7) 0.5238(4) 0.143(3) Uani 1 1 d . B . H20A H 0.8088 0.1187 0.5162 0.215 Uiso 1 1 calc R . . H20B H 0.7252 0.2052 0.4893 0.215 Uiso 1 1 calc R . . H20C H 0.6465 0.1295 0.5295 0.215 Uiso 1 1 calc R . . H1 H 0.346(5) -0.114(3) 0.7905(19) 0.042(13) Uiso 1 1 d . . . H3 H 0.668(4) 0.031(3) 0.7319(18) 0.041(11) Uiso 1 1 d . . . H6A H 0.319(6) 0.300(4) 0.809(3) 0.070(19) Uiso 1 1 d . . . H6B H 0.428(9) 0.318(6) 0.784(3) 0.06(2) Uiso 0.65 1 d P . . H5B H 0.682(6) 0.766(4) 0.872(3) 0.077(18) Uiso 1 1 d . . . H7B H 0.841(8) 0.665(5) 0.745(3) 0.10(2) Uiso 1 1 d . . . H5A H 0.766(7) 0.703(5) 0.834(3) 0.10(3) Uiso 1 1 d . . . H7A H 0.847(8) 0.745(5) 0.726(3) 0.09(2) Uiso 1 1 d . . . C19 C 0.9057(10) 0.2650(8) 0.5684(5) 0.188(6) Uani 1 1 d . B 1 H19A H 0.8958 0.3145 0.5385 0.282 Uiso 1 1 calc R B 1 H19B H 0.9748 0.2201 0.5544 0.282 Uiso 1 1 calc R B 1 H19C H 0.9359 0.2916 0.6069 0.282 Uiso 1 1 calc R B 1 H4 H 0.387(5) 0.109(3) 0.6102(19) 0.051(12) Uiso 1 1 d . C 1 H6C H 0.331(9) 0.373(6) 0.829(4) 0.006(18) Uiso 0.35 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O3 0.0641(19) 0.0396(15) 0.070(2) 0.0014(15) -0.0053(17) 0.0052(14) O1 0.062(2) 0.0510(17) 0.083(2) -0.0076(16) -0.0082(18) 0.0102(16) N4 0.060(2) 0.049(2) 0.056(2) -0.0041(18) -0.0066(19) 0.0015(19) O4 0.080(2) 0.0518(17) 0.075(2) -0.0026(16) -0.0056(19) 0.0118(18) C10 0.045(2) 0.043(2) 0.0363(19) -0.0036(17) -0.0006(17) -0.0022(18) O2 0.0585(17) 0.0378(14) 0.076(2) 0.0086(14) 0.0004(17) -0.0007(14) N1 0.047(2) 0.0375(18) 0.056(2) -0.0070(17) 0.0007(16) 0.0029(16) N2 0.0360(17) 0.0454(17) 0.0428(17) -0.0003(15) 0.0043(15) 0.0030(14) N3 0.056(2) 0.0385(16) 0.0435(18) 0.0069(15) 0.0001(17) 0.0054(16) C15 0.0310(18) 0.042(2) 0.054(2) 0.0009(18) 0.0022(18) -0.0031(16) C16 0.053(2) 0.046(2) 0.049(2) 0.0059(19) -0.005(2) 0.002(2) C2 0.041(2) 0.0356(18) 0.051(2) -0.0006(18) 0.0035(17) -0.0058(16) C11 0.039(2) 0.043(2) 0.043(2) 0.0005(17) 0.0064(18) -0.0008(17) C1 0.044(2) 0.046(2) 0.054(2) 0.004(2) 0.006(2) -0.0024(18) C9 0.058(3) 0.065(3) 0.046(2) 0.009(2) 0.010(2) 0.004(2) C4 0.039(2) 0.055(2) 0.041(2) -0.0050(19) 0.0114(18) 0.0021(18) C21 0.062(3) 0.046(2) 0.045(2) 0.0075(19) 0.004(2) 0.000(2) C26 0.049(2) 0.048(2) 0.068(3) -0.001(2) -0.006(2) -0.008(2) C5 0.046(2) 0.068(3) 0.058(3) -0.002(2) 0.006(2) 0.008(2) O6 0.108(4) 0.091(3) 0.088(4) -0.017(3) 0.011(3) 0.006(3) C13 0.044(2) 0.081(3) 0.076(3) 0.000(3) -0.002(2) -0.002(3) C3 0.044(2) 0.060(3) 0.061(3) -0.005(2) 0.014(2) -0.009(2) C22 0.071(3) 0.065(3) 0.055(3) -0.009(2) -0.012(2) -0.001(3) C25 0.054(3) 0.066(3) 0.072(3) -0.006(2) -0.014(2) -0.006(3) C12 0.051(3) 0.065(3) 0.062(3) 0.007(2) -0.008(2) -0.016(2) C17 0.055(3) 0.072(3) 0.052(3) 0.014(2) -0.007(2) -0.008(2) C24 0.068(3) 0.056(3) 0.061(3) -0.001(2) -0.016(3) 0.004(2) C8 0.049(3) 0.116(5) 0.048(3) -0.002(3) -0.007(2) -0.004(3) C7 0.061(3) 0.088(4) 0.077(4) -0.031(3) 0.001(3) -0.016(3) C14 0.051(3) 0.057(3) 0.072(3) 0.004(2) 0.000(2) 0.008(2) C23 0.070(3) 0.048(2) 0.064(3) -0.007(2) -0.014(2) -0.005(2) C6 0.072(3) 0.051(3) 0.101(4) -0.016(3) 0.013(3) 0.000(3) C18 0.082(4) 0.114(5) 0.078(4) 0.032(4) 0.013(3) -0.007(4) O5 0.081(3) 0.047(2) 0.112(4) 0.008(2) -0.007(3) 0.0085(19) O7 0.104(4) 0.070(3) 0.132(5) -0.007(3) -0.002(3) -0.022(3) C20 0.161(9) 0.170(8) 0.099(6) 0.023(6) 0.021(6) -0.011(8) C19 0.128(7) 0.269(13) 0.168(9) 0.143(9) -0.020(7) -0.079(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 O3 C15 1.221(5) . ? O1 C1 1.237(5) . ? N4 C21 1.326(6) . ? N4 C22 1.455(6) . ? N4 H4 0.90(5) . ? O4 C21 1.225(5) . ? C10 O2 1.218(5) . ? C10 N2 1.341(5) . ? C10 C2 1.519(6) . ? N1 C1 1.332(6) . ? N1 C2 1.448(5) . ? N1 H1 0.74(4) . ? N2 C11 1.470(5) . ? N2 C14 1.474(5) . ? N3 C15 1.332(5) . ? N3 C16 1.465(5) . ? N3 H3 0.91(4) . ? C15 C11 1.521(6) . ? C16 C17 1.525(6) . ? C16 C21 1.525(6) . ? C16 H16 0.9800 . ? C2 C3 1.544(6) . ? C2 H2 0.9800 . ? C11 C12 1.548(6) . ? C11 H11 0.9800 . ? C1 C26 1.503(6) . ? C9 C4 1.388(6) . ? C9 C8 1.391(7) . ? C9 H9 0.9300 . ? C4 C5 1.375(6) . ? C4 C3 1.507(6) . ? C26 C25 1.515(7) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C5 C6 1.382(7) . ? C5 H5 0.9300 . ? O6 H6A 0.87(6) . ? O6 H6B 0.96(9) . ? O6 H6C 0.97(9) . ? C13 C12 1.510(7) . ? C13 C14 1.518(7) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C22 C23 1.516(7) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C25 C24 1.507(7) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C17 C18 1.517(7) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C24 C23 1.536(7) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C8 C7 1.380(8) . ? C8 H8 0.9300 . ? C7 C6 1.361(8) . ? C7 H7 0.9300 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C6 H6 0.9300 . ? C18 C20 1.405(11) . ? C18 C19 1.517(10) . ? C18 H18 0.9800 . ? O5 H5B 0.83(6) . ? O5 H5A 0.96(7) . ? O7 H7B 0.91(8) . ? O7 H7A 0.88(7) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C21 N4 C22 122.8(4) . . ? C21 N4 H4 118(3) . . ? C22 N4 H4 118(3) . . ? O2 C10 N2 122.7(4) . . ? O2 C10 C2 117.8(4) . . ? N2 C10 C2 119.5(3) . . ? C1 N1 C2 122.6(4) . . ? C1 N1 H1 117(4) . . ? C2 N1 H1 121(4) . . ? C10 N2 C11 126.9(3) . . ? C10 N2 C14 120.3(3) . . ? C11 N2 C14 111.3(3) . . ? C15 N3 C16 121.0(3) . . ? C15 N3 H3 115(3) . . ? C16 N3 H3 123(3) . . ? O3 C15 N3 123.8(4) . . ? O3 C15 C11 118.6(4) . . ? N3 C15 C11 117.5(3) . . ? N3 C16 C17 109.7(4) . . ? N3 C16 C21 107.4(3) . . ? C17 C16 C21 113.2(4) . . ? N3 C16 H16 108.8 . . ? C17 C16 H16 108.8 . . ? C21 C16 H16 108.8 . . ? N1 C2 C10 107.3(3) . . ? N1 C2 C3 111.4(3) . . ? C10 C2 C3 108.5(3) . . ? N1 C2 H2 109.9 . . ? C10 C2 H2 109.9 . . ? C3 C2 H2 109.9 . . ? N2 C11 C15 116.3(3) . . ? N2 C11 C12 103.4(3) . . ? C15 C11 C12 109.6(3) . . ? N2 C11 H11 109.1 . . ? C15 C11 H11 109.1 . . ? C12 C11 H11 109.1 . . ? O1 C1 N1 121.0(4) . . ? O1 C1 C26 122.2(4) . . ? N1 C1 C26 116.8(4) . . ? C4 C9 C8 120.3(5) . . ? C4 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C5 C4 C9 118.2(4) . . ? C5 C4 C3 120.8(4) . . ? C9 C4 C3 120.9(4) . . ? O4 C21 N4 124.3(4) . . ? O4 C21 C16 120.3(4) . . ? N4 C21 C16 115.4(4) . . ? C1 C26 C25 113.2(4) . . ? C1 C26 H26A 108.9 . . ? C25 C26 H26A 108.9 . . ? C1 C26 H26B 108.9 . . ? C25 C26 H26B 108.9 . . ? H26A C26 H26B 107.8 . . ? C4 C5 C6 122.1(5) . . ? C4 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? H6A O6 H6B 81(6) . . ? H6A O6 H6C 74(6) . . ? H6B O6 H6C 106(7) . . ? C12 C13 C14 102.8(4) . . ? C12 C13 H13A 111.2 . . ? C14 C13 H13A 111.2 . . ? C12 C13 H13B 111.2 . . ? C14 C13 H13B 111.2 . . ? H13A C13 H13B 109.1 . . ? C4 C3 C2 112.3(3) . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3B 109.2 . . ? C2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? N4 C22 C23 112.9(4) . . ? N4 C22 H22A 109.0 . . ? C23 C22 H22A 109.0 . . ? N4 C22 H22B 109.0 . . ? C23 C22 H22B 109.0 . . ? H22A C22 H22B 107.8 . . ? C24 C25 C26 113.9(4) . . ? C24 C25 H25A 108.8 . . ? C26 C25 H25A 108.8 . . ? C24 C25 H25B 108.8 . . ? C26 C25 H25B 108.8 . . ? H25A C25 H25B 107.7 . . ? C13 C12 C11 105.3(4) . . ? C13 C12 H12A 110.7 . . ? C11 C12 H12A 110.7 . . ? C13 C12 H12B 110.7 . . ? C11 C12 H12B 110.7 . . ? H12A C12 H12B 108.8 . . ? C18 C17 C16 114.7(4) . . ? C18 C17 H17A 108.6 . . ? C16 C17 H17A 108.6 . . ? C18 C17 H17B 108.6 . . ? C16 C17 H17B 108.6 . . ? H17A C17 H17B 107.6 . . ? C25 C24 C23 115.5(4) . . ? C25 C24 H24A 108.4 . . ? C23 C24 H24A 108.4 . . ? C25 C24 H24B 108.4 . . ? C23 C24 H24B 108.4 . . ? H24A C24 H24B 107.5 . . ? C7 C8 C9 119.4(5) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C6 C7 C8 121.1(5) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? N2 C14 C13 103.5(4) . . ? N2 C14 H14A 111.1 . . ? C13 C14 H14A 111.1 . . ? N2 C14 H14B 111.1 . . ? C13 C14 H14B 111.1 . . ? H14A C14 H14B 109.0 . . ? C22 C23 C24 112.8(4) . . ? C22 C23 H23A 109.0 . . ? C24 C23 H23A 109.0 . . ? C22 C23 H23B 109.0 . . ? C24 C23 H23B 109.0 . . ? H23A C23 H23B 107.8 . . ? C7 C6 C5 118.9(5) . . ? C7 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C20 C18 C17 112.7(7) . . ? C20 C18 C19 108.8(8) . . ? C17 C18 C19 109.7(6) . . ? C20 C18 H18 108.5 . . ? C17 C18 H18 108.5 . . ? C19 C18 H18 108.5 . . ? H5B O5 H5A 109(6) . . ? H7B O7 H7A 86(6) . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.417 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.041