# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Jeremy Sanders' 'Ho Yu Au-Yeung.' 'Sijbren Otto' 'G Dan Pantos' 'Paolo Pengo' _publ_contact_author_name 'Jeremy Sanders' _publ_contact_author_email JKMS@CAM.AC.UK _publ_section_title ; Templated Amplification of a Naphthalenediimide-based Receptor from a Donor-Acceptor Dynamic Combinatorial Library in Water ; # Attachment 'js0706.cif' data_js0706 _database_code_depnum_ccdc_archive 'CCDC 703957' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H38 N4 O4 2+, 2(Cl 1-), 3.25(H2 O)' _chemical_formula_sum 'C24 H44.50 Cl2 N4 O7.25' _chemical_formula_weight 576.04 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.5572(3) _cell_length_b 11.3888(3) _cell_length_c 13.1194(4) _cell_angle_alpha 73.187(2) _cell_angle_beta 82.840(2) _cell_angle_gamma 83.681(2) _cell_volume 1493.64(7) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 19735 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 30.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 617 _exptl_absorpt_coefficient_mu 0.264 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.911 _exptl_absorpt_correction_T_max 0.972 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The fourth water solvate molecule was assigned occupancy 0.25. This is the best of THREE separate data collections, 2 @ 180K, 1 @ 270K. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 22846 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0611 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 32.00 _reflns_number_total 10174 _reflns_number_gt 6847 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0327P)^2^+0.9254P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10174 _refine_ls_number_parameters 369 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1045 _refine_ls_R_factor_gt 0.0617 _refine_ls_wR_factor_ref 0.1356 _refine_ls_wR_factor_gt 0.1166 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 Cl1 Cl 0.04311(5) 0.15013(4) 0.10642(4) 0.03522(12) Uani 1 1 d . . . Cl2 Cl -0.03380(5) 0.31076(5) 0.44055(4) 0.03652(12) Uani 1 1 d . . . O1 O -0.53269(12) 0.02604(11) 0.12962(10) 0.0292(3) Uani 1 1 d . . . O2 O -0.54009(14) 0.34197(12) 0.11908(14) 0.0431(4) Uani 1 1 d . . . O3 O -0.48980(12) -0.51583(11) 0.34218(11) 0.0319(3) Uani 1 1 d . . . O4 O -0.41612(15) -0.83669(12) 0.44798(13) 0.0446(4) Uani 1 1 d . . . N1 N -0.38697(14) 0.21494(13) 0.06169(12) 0.0271(3) Uani 1 1 d . . . H1N H -0.3671 0.1421 0.0508 0.033 Uiso 1 1 calc R . . N2 N -0.18653(14) 0.45471(14) -0.13266(12) 0.0276(3) Uani 1 1 d . . . N3 N -0.57921(15) -0.70673(14) 0.48865(12) 0.0295(3) Uani 1 1 d . . . H3N H -0.6189 -0.6328 0.4690 0.035 Uiso 1 1 calc R . . N4 N -0.81062(15) -0.94372(14) 0.64238(12) 0.0283(3) Uani 1 1 d . . . C1 C -0.57768(17) -0.08178(16) 0.19647(14) 0.0254(3) Uani 1 1 d . . . C2 C -0.69002(18) -0.08662(17) 0.26181(16) 0.0315(4) Uani 1 1 d . . . H2 H -0.7454 -0.0143 0.2587 0.038 Uiso 1 1 calc R . . C3 C -0.72272(18) -0.20032(17) 0.33398(16) 0.0329(4) Uani 1 1 d . . . H3 H -0.7998 -0.2034 0.3802 0.039 Uiso 1 1 calc R . . C4 C -0.64544(17) -0.30593(16) 0.33850(14) 0.0270(4) Uani 1 1 d . . . H4 H -0.6681 -0.3812 0.3885 0.032 Uiso 1 1 calc R . . C5 C -0.44799(17) -0.41046(15) 0.26961(14) 0.0258(3) Uani 1 1 d . . . C6 C -0.33631(18) -0.40632(17) 0.20316(15) 0.0290(4) Uani 1 1 d . . . H6 H -0.2820 -0.4790 0.2050 0.035 Uiso 1 1 calc R . . C7 C -0.30335(18) -0.29239(17) 0.13202(14) 0.0287(4) Uani 1 1 d . . . H7 H -0.2258 -0.2892 0.0864 0.034 Uiso 1 1 calc R . . C8 C -0.38047(17) -0.18616(16) 0.12710(14) 0.0260(4) Uani 1 1 d . . . H8 H -0.3565 -0.1107 0.0783 0.031 Uiso 1 1 calc R . . C9 C -0.49631(16) -0.18956(15) 0.19532(13) 0.0229(3) Uani 1 1 d . . . C10 C -0.53146(16) -0.30283(15) 0.26832(13) 0.0228(3) Uani 1 1 d . . . C11 C -0.59126(17) 0.13732(16) 0.14913(16) 0.0291(4) Uani 1 1 d . . . H11A H -0.6128 0.1242 0.2270 0.035 Uiso 1 1 calc R . . H11B H -0.6718 0.1607 0.1142 0.035 Uiso 1 1 calc R . . C12 C -0.50289(17) 0.24035(16) 0.10643(15) 0.0275(4) Uani 1 1 d . . . C13 C -0.29249(17) 0.30606(17) 0.03041(15) 0.0280(4) Uani 1 1 d . . . H13A H -0.2059 0.2648 0.0426 0.034 Uiso 1 1 calc R . . H13B H -0.3108 0.3645 0.0745 0.034 Uiso 1 1 calc R . . C14 C -0.29698(17) 0.37545(17) -0.08735(15) 0.0280(4) Uani 1 1 d . . . H14A H -0.2968 0.3153 -0.1288 0.034 Uiso 1 1 calc R . . H14B H -0.3782 0.4282 -0.0962 0.034 Uiso 1 1 calc R . . C15 C -0.1716(2) 0.53479(18) -0.06297(17) 0.0356(4) Uani 1 1 d . . . H15A H -0.1430 0.4836 0.0053 0.053 Uiso 1 1 calc R . . H15B H -0.2539 0.5795 -0.0499 0.053 Uiso 1 1 calc R . . H15C H -0.1079 0.5937 -0.0987 0.053 Uiso 1 1 calc R . . C16 C -0.2153(2) 0.5356(2) -0.24107(16) 0.0387(5) Uani 1 1 d . . . H16A H -0.1428 0.5851 -0.2738 0.058 Uiso 1 1 calc R . . H16B H -0.2923 0.5901 -0.2338 0.058 Uiso 1 1 calc R . . H16C H -0.2294 0.4843 -0.2865 0.058 Uiso 1 1 calc R . . C17 C -0.0644(2) 0.3779(2) -0.1449(2) 0.0464(6) Uani 1 1 d . . . H17A H -0.0451 0.3237 -0.0747 0.070 Uiso 1 1 calc R . . H17B H 0.0054 0.4316 -0.1751 0.070 Uiso 1 1 calc R . . H17C H -0.0735 0.3281 -0.1929 0.070 Uiso 1 1 calc R . . C18 C -0.41113(19) -0.62724(16) 0.34854(16) 0.0313(4) Uani 1 1 d . . . H18A H -0.3252 -0.6181 0.3668 0.038 Uiso 1 1 calc R . . H18B H -0.4009 -0.6448 0.2782 0.038 Uiso 1 1 calc R . . C19 C -0.47061(18) -0.73273(17) 0.43259(15) 0.0298(4) Uani 1 1 d . . . C20 C -0.63326(18) -0.79811(17) 0.58145(14) 0.0292(4) Uani 1 1 d . . . H20A H -0.6775 -0.7568 0.6343 0.035 Uiso 1 1 calc R . . H20B H -0.5636 -0.8560 0.6156 0.035 Uiso 1 1 calc R . . C21 C -0.72775(18) -0.86899(17) 0.54852(14) 0.0293(4) Uani 1 1 d . . . H21A H -0.7837 -0.8100 0.4988 0.035 Uiso 1 1 calc R . . H21B H -0.6796 -0.9250 0.5095 0.035 Uiso 1 1 calc R . . C22 C -0.89982(19) -0.86205(19) 0.69515(18) 0.0387(5) Uani 1 1 d . . . H22A H -0.9580 -0.9123 0.7507 0.058 Uiso 1 1 calc R . . H22B H -0.9497 -0.8034 0.6416 0.058 Uiso 1 1 calc R . . H22C H -0.8501 -0.8171 0.7276 0.058 Uiso 1 1 calc R . . C23 C -0.8889(2) -1.0171(2) 0.59946(19) 0.0479(6) Uani 1 1 d . . . H23A H -0.9464 -1.0642 0.6578 0.072 Uiso 1 1 calc R . . H23B H -0.8320 -1.0738 0.5676 0.072 Uiso 1 1 calc R . . H23C H -0.9396 -0.9615 0.5448 0.072 Uiso 1 1 calc R . . C24 C -0.73140(19) -1.03015(17) 0.72375(15) 0.0330(4) Uani 1 1 d . . . H24A H -0.7873 -1.0834 0.7791 0.049 Uiso 1 1 calc R . . H24B H -0.6851 -0.9828 0.7566 0.049 Uiso 1 1 calc R . . H24C H -0.6700 -1.0808 0.6888 0.049 Uiso 1 1 calc R . . O1W O -0.11337(15) 0.35197(14) 0.20743(12) 0.0412(3) Uani 1 1 d D . . H11W H -0.090(3) 0.343(3) 0.2783(16) 0.094(5) Uiso 1 1 d D . . H12W H -0.071(3) 0.284(2) 0.181(2) 0.094(5) Uiso 1 1 d D . . O2W O -1.17731(16) -0.94411(18) 1.00013(18) 0.0623(5) Uani 1 1 d D . . H21W H -1.149(3) -1.008(2) 0.965(2) 0.094(5) Uiso 1 1 d D . . H22W H -1.104(2) -0.923(3) 1.029(2) 0.094(5) Uiso 1 1 d D . . O3W O 0.18275(15) 0.44630(15) 0.51210(15) 0.0489(4) Uani 1 1 d D . . H32W H 0.121(3) 0.405(3) 0.490(3) 0.094(5) Uiso 1 1 d D . . H31W H 0.145(3) 0.515(2) 0.537(3) 0.094(5) Uiso 1 1 d D . . O4W O 0.1583(6) 0.1645(6) 0.3142(5) 0.0430(14) Uiso 0.25 1 d PD . . H41W H 0.118(9) 0.158(11) 0.251(6) 0.094(5) Uiso 0.25 1 d PD . . H42W H 0.091(8) 0.200(11) 0.361(7) 0.094(5) Uiso 0.25 1 d PD . . 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 Cl1 0.0340(2) 0.0332(2) 0.0399(3) -0.0140(2) 0.00046(19) -0.00345(18) Cl2 0.0377(3) 0.0394(3) 0.0324(2) -0.0100(2) 0.00261(19) -0.0094(2) O1 0.0321(7) 0.0197(6) 0.0311(7) -0.0027(5) 0.0061(5) -0.0050(5) O2 0.0356(8) 0.0246(7) 0.0661(11) -0.0131(7) 0.0076(7) -0.0029(6) O3 0.0335(7) 0.0191(6) 0.0362(7) -0.0006(5) 0.0079(6) -0.0046(5) O4 0.0550(10) 0.0224(7) 0.0486(9) -0.0056(6) 0.0121(7) -0.0011(6) N1 0.0254(7) 0.0213(7) 0.0323(8) -0.0047(6) 0.0018(6) -0.0042(6) N2 0.0254(7) 0.0262(7) 0.0288(8) -0.0046(6) 0.0019(6) -0.0055(6) N3 0.0311(8) 0.0219(7) 0.0314(8) -0.0020(6) 0.0020(6) -0.0049(6) N4 0.0307(8) 0.0255(7) 0.0281(8) -0.0030(6) -0.0048(6) -0.0090(6) C1 0.0258(8) 0.0230(8) 0.0255(8) -0.0029(6) 0.0001(7) -0.0074(6) C2 0.0280(9) 0.0247(8) 0.0384(10) -0.0056(8) 0.0036(8) -0.0041(7) C3 0.0264(9) 0.0303(9) 0.0383(10) -0.0057(8) 0.0078(8) -0.0092(7) C4 0.0272(9) 0.0251(8) 0.0265(9) -0.0039(7) 0.0037(7) -0.0091(7) C5 0.0301(9) 0.0212(8) 0.0254(8) -0.0044(6) -0.0007(7) -0.0074(7) C6 0.0298(9) 0.0244(8) 0.0315(9) -0.0078(7) 0.0032(7) -0.0038(7) C7 0.0293(9) 0.0292(9) 0.0261(9) -0.0071(7) 0.0059(7) -0.0074(7) C8 0.0279(9) 0.0257(8) 0.0232(8) -0.0046(7) 0.0024(7) -0.0085(7) C9 0.0241(8) 0.0222(8) 0.0232(8) -0.0052(6) -0.0020(6) -0.0082(6) C10 0.0244(8) 0.0213(7) 0.0233(8) -0.0059(6) -0.0006(6) -0.0074(6) C11 0.0266(9) 0.0213(8) 0.0360(10) -0.0049(7) 0.0030(7) -0.0027(7) C12 0.0262(9) 0.0225(8) 0.0306(9) -0.0021(7) -0.0012(7) -0.0038(7) C13 0.0265(9) 0.0271(8) 0.0290(9) -0.0043(7) -0.0017(7) -0.0074(7) C14 0.0260(9) 0.0292(9) 0.0286(9) -0.0053(7) -0.0010(7) -0.0100(7) C15 0.0381(11) 0.0330(10) 0.0378(11) -0.0088(8) -0.0030(8) -0.0153(8) C16 0.0432(12) 0.0399(11) 0.0278(10) 0.0002(8) 0.0014(8) -0.0123(9) C17 0.0305(11) 0.0414(12) 0.0585(14) -0.0089(11) 0.0119(10) 0.0021(9) C18 0.0337(10) 0.0216(8) 0.0342(10) -0.0049(7) 0.0064(8) -0.0030(7) C19 0.0354(10) 0.0241(8) 0.0289(9) -0.0063(7) 0.0028(7) -0.0080(7) C20 0.0327(9) 0.0286(9) 0.0250(9) -0.0035(7) -0.0015(7) -0.0095(7) C21 0.0364(10) 0.0271(9) 0.0235(8) -0.0034(7) -0.0026(7) -0.0089(7) C22 0.0309(10) 0.0378(11) 0.0412(11) -0.0038(9) 0.0025(8) -0.0016(8) C23 0.0577(14) 0.0443(12) 0.0451(13) -0.0047(10) -0.0155(11) -0.0279(11) C24 0.0377(10) 0.0287(9) 0.0284(9) 0.0000(7) -0.0064(8) -0.0030(8) O1W 0.0420(9) 0.0436(9) 0.0386(8) -0.0141(7) -0.0054(7) 0.0030(7) O2W 0.0361(9) 0.0714(13) 0.0990(16) -0.0590(12) -0.0007(9) 0.0006(8) O3W 0.0361(8) 0.0441(9) 0.0701(12) -0.0233(9) -0.0037(8) -0.0006(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.3799(19) . ? O1 C11 1.425(2) . ? O2 C12 1.231(2) . ? O3 C5 1.376(2) . ? O3 C18 1.425(2) . ? O4 C19 1.231(2) . ? N1 C12 1.329(2) . ? N1 C13 1.456(2) . ? N1 H1N 0.8800 . ? N2 C17 1.494(2) . ? N2 C15 1.498(2) . ? N2 C16 1.500(2) . ? N2 C14 1.509(2) . ? N3 C19 1.336(2) . ? N3 C20 1.454(2) . ? N3 H3N 0.8800 . ? N4 C23 1.496(2) . ? N4 C24 1.497(2) . ? N4 C22 1.500(3) . ? N4 C21 1.515(2) . ? C1 C2 1.370(2) . ? C1 C9 1.421(2) . ? C2 C3 1.414(2) . ? C2 H2 0.9500 . ? C3 C4 1.368(3) . ? C3 H3 0.9500 . ? C4 C10 1.418(2) . ? C4 H4 0.9500 . ? C5 C6 1.373(2) . ? C5 C10 1.426(2) . ? C6 C7 1.412(2) . ? C6 H6 0.9500 . ? C7 C8 1.372(3) . ? C7 H7 0.9500 . ? C8 C9 1.420(2) . ? C8 H8 0.9500 . ? C9 C10 1.422(2) . ? C11 C12 1.514(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C13 C14 1.522(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.510(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C20 C21 1.523(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? O1W H11W 0.968(17) . ? O1W H12W 0.981(17) . ? O2W H21W 0.977(17) . ? O2W H22W 0.984(17) . ? O3W H32W 0.967(17) . ? O3W H31W 0.963(17) . ? O4W H41W 1.00(2) . ? O4W H42W 1.01(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C11 116.36(14) . . ? C5 O3 C18 117.43(14) . . ? C12 N1 C13 120.83(16) . . ? C12 N1 H1N 119.6 . . ? C13 N1 H1N 119.6 . . ? C17 N2 C15 109.74(16) . . ? C17 N2 C16 108.56(16) . . ? C15 N2 C16 108.62(15) . . ? C17 N2 C14 111.18(15) . . ? C15 N2 C14 110.73(14) . . ? C16 N2 C14 107.93(14) . . ? C19 N3 C20 121.35(16) . . ? C19 N3 H3N 119.3 . . ? C20 N3 H3N 119.3 . . ? C23 N4 C24 108.83(15) . . ? C23 N4 C22 108.48(17) . . ? C24 N4 C22 109.23(15) . . ? C23 N4 C21 107.31(15) . . ? C24 N4 C21 111.62(14) . . ? C22 N4 C21 111.27(14) . . ? C2 C1 O1 123.62(16) . . ? C2 C1 C9 121.55(15) . . ? O1 C1 C9 114.80(15) . . ? C1 C2 C3 119.37(17) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 121.25(17) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C10 119.83(16) . . ? C3 C4 H4 120.1 . . ? C10 C4 H4 120.1 . . ? C6 C5 O3 124.21(16) . . ? C6 C5 C10 121.68(15) . . ? O3 C5 C10 114.11(15) . . ? C5 C6 C7 119.02(17) . . ? C5 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? C8 C7 C6 121.70(16) . . ? C8 C7 H7 119.1 . . ? C6 C7 H7 119.1 . . ? C7 C8 C9 119.69(15) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C8 C9 C1 122.17(15) . . ? C8 C9 C10 119.83(16) . . ? C1 C9 C10 117.95(15) . . ? C4 C10 C9 119.95(16) . . ? C4 C10 C5 121.97(15) . . ? C9 C10 C5 118.07(15) . . ? O1 C11 C12 110.96(14) . . ? O1 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? O1 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? O2 C12 N1 123.39(16) . . ? O2 C12 C11 118.25(16) . . ? N1 C12 C11 118.28(16) . . ? N1 C13 C14 109.53(14) . . ? N1 C13 H13A 109.8 . . ? C14 C13 H13A 109.8 . . ? N1 C13 H13B 109.8 . . ? C14 C13 H13B 109.8 . . ? H13A C13 H13B 108.2 . . ? N2 C14 C13 113.42(14) . . ? N2 C14 H14A 108.9 . . ? C13 C14 H14A 108.9 . . ? N2 C14 H14B 108.9 . . ? C13 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? N2 C15 H15A 109.5 . . ? N2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N2 C16 H16A 109.5 . . ? N2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N2 C17 H17A 109.5 . . ? N2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O3 C18 C19 110.30(15) . . ? O3 C18 H18A 109.6 . . ? C19 C18 H18A 109.6 . . ? O3 C18 H18B 109.6 . . ? C19 C18 H18B 109.6 . . ? H18A C18 H18B 108.1 . . ? O4 C19 N3 123.37(17) . . ? O4 C19 C18 119.14(17) . . ? N3 C19 C18 117.46(16) . . ? N3 C20 C21 110.43(15) . . ? N3 C20 H20A 109.6 . . ? C21 C20 H20A 109.6 . . ? N3 C20 H20B 109.6 . . ? C21 C20 H20B 109.6 . . ? H20A C20 H20B 108.1 . . ? N4 C21 C20 113.27(15) . . ? N4 C21 H21A 108.9 . . ? C20 C21 H21A 108.9 . . ? N4 C21 H21B 108.9 . . ? C20 C21 H21B 108.9 . . ? H21A C21 H21B 107.7 . . ? N4 C22 H22A 109.5 . . ? N4 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N4 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N4 C23 H23A 109.5 . . ? N4 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N4 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N4 C24 H24A 109.5 . . ? N4 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N4 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? H11W O1W H12W 110(2) . . ? H21W O2W H22W 109(2) . . ? H32W O3W H31W 113(2) . . ? H41W O4W H42W 109(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 C11 O1 C1 C2 14.9(3) . . . . ? C11 O1 C1 C9 -163.35(16) . . . . ? O1 C1 C2 C3 -174.75(18) . . . . ? C9 C1 C2 C3 3.4(3) . . . . ? C1 C2 C3 C4 -1.1(3) . . . . ? C2 C3 C4 C10 -1.3(3) . . . . ? C18 O3 C5 C6 0.3(3) . . . . ? C18 O3 C5 C10 -179.71(16) . . . . ? O3 C5 C6 C7 -179.87(17) . . . . ? C10 C5 C6 C7 0.2(3) . . . . ? C5 C6 C7 C8 -0.5(3) . . . . ? C6 C7 C8 C9 0.4(3) . . . . ? C7 C8 C9 C1 177.71(17) . . . . ? C7 C8 C9 C10 0.1(3) . . . . ? C2 C1 C9 C8 179.20(18) . . . . ? O1 C1 C9 C8 -2.5(2) . . . . ? C2 C1 C9 C10 -3.2(3) . . . . ? O1 C1 C9 C10 175.15(15) . . . . ? C3 C4 C10 C9 1.5(3) . . . . ? C3 C4 C10 C5 -179.75(18) . . . . ? C8 C9 C10 C4 178.36(16) . . . . ? C1 C9 C10 C4 0.7(2) . . . . ? C8 C9 C10 C5 -0.4(2) . . . . ? C1 C9 C10 C5 -178.12(16) . . . . ? C6 C5 C10 C4 -178.48(18) . . . . ? O3 C5 C10 C4 1.6(2) . . . . ? C6 C5 C10 C9 0.3(3) . . . . ? O3 C5 C10 C9 -179.67(15) . . . . ? C1 O1 C11 C12 156.19(15) . . . . ? C13 N1 C12 O2 3.9(3) . . . . ? C13 N1 C12 C11 -172.84(16) . . . . ? O1 C11 C12 O2 -178.90(17) . . . . ? O1 C11 C12 N1 -2.0(2) . . . . ? C12 N1 C13 C14 -95.1(2) . . . . ? C17 N2 C14 C13 71.8(2) . . . . ? C15 N2 C14 C13 -50.5(2) . . . . ? C16 N2 C14 C13 -169.23(16) . . . . ? N1 C13 C14 N2 -169.04(15) . . . . ? C5 O3 C18 C19 179.41(16) . . . . ? C20 N3 C19 O4 7.4(3) . . . . ? C20 N3 C19 C18 -170.74(17) . . . . ? O3 C18 C19 O4 179.07(18) . . . . ? O3 C18 C19 N3 -2.7(3) . . . . ? C19 N3 C20 C21 -91.7(2) . . . . ? C23 N4 C21 C20 -174.65(17) . . . . ? C24 N4 C21 C20 -55.5(2) . . . . ? C22 N4 C21 C20 66.8(2) . . . . ? N3 C20 C21 N4 -166.33(15) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 32.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.352 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.058 # Attachment 'js0802.cif' data_js0802 _database_code_depnum_ccdc_archive 'CCDC 703958' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H38 N4 O4, C18 H8 N2 O8, 6(H2 O)' _chemical_formula_sum 'C42 H58 N6 O18' _chemical_formula_weight 934.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3691(1) _cell_length_b 8.4678(2) _cell_length_c 15.9082(3) _cell_angle_alpha 85.201(1) _cell_angle_beta 75.792(1) _cell_angle_gamma 83.444(1) _cell_volume 1083.94(4) _cell_formula_units_Z 1 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 12198 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 34.97 _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.522 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The water hydrogen atoms were all located and their positions were refined satisfactorily. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 17034 _diffrn_reflns_av_R_equivalents 0.0763 _diffrn_reflns_av_sigmaI/netI 0.0587 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.67 _diffrn_reflns_theta_max 34.96 _reflns_number_total 9240 _reflns_number_gt 7435 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0692P)^2^+0.4259P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9240 _refine_ls_number_parameters 321 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0744 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1618 _refine_ls_wR_factor_gt 0.1470 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.97375(11) 0.29410(11) 0.86059(6) 0.02570(17) Uani 1 1 d . . . N1 N 0.90278(13) 0.25786(12) 0.70984(7) 0.02324(18) Uani 1 1 d . . . H1 H 0.8487 0.3266 0.7479 0.028 Uiso 1 1 calc R . . C1 C 1.01593(13) 0.32080(13) 0.93584(7) 0.02071(18) Uani 1 1 d . . . O2 O 1.07554(14) 0.02974(12) 0.68922(7) 0.0355(2) Uani 1 1 d . . . N2 N 0.64766(12) 0.09393(11) 0.61904(6) 0.02189(17) Uani 1 1 d . . . C2 C 1.09120(15) 0.20576(14) 0.98368(8) 0.0244(2) Uani 1 1 d . . . H2 H 1.1146 0.0994 0.9661 0.029 Uiso 1 1 calc R . . C3 C 1.13342(14) 0.24759(14) 1.05942(8) 0.0238(2) Uani 1 1 d . . . H3 H 1.1849 0.1678 1.0924 0.029 Uiso 1 1 calc R . . C4 C 1.10205(13) 0.39964(14) 1.08622(7) 0.02130(18) Uani 1 1 d . . . H4 H 1.1331 0.4253 1.1366 0.026 Uiso 1 1 calc R . . C5 C 0.97749(12) 0.48093(13) 0.96198(6) 0.01866(17) Uani 1 1 d . . . C6 C 1.04254(15) 0.14752(14) 0.82245(8) 0.0251(2) Uani 1 1 d . . . H6A H 0.9944 0.0580 0.8607 0.030 Uiso 1 1 calc R . . H6B H 1.1636 0.1349 0.8171 0.030 Uiso 1 1 calc R . . C7 C 1.00851(14) 0.14193(14) 0.73378(8) 0.0236(2) Uani 1 1 d . . . C8 C 0.87506(15) 0.27294(14) 0.62266(7) 0.0243(2) Uani 1 1 d . . . H8A H 0.9480 0.1891 0.5881 0.029 Uiso 1 1 calc R . . H8B H 0.9082 0.3773 0.5952 0.029 Uiso 1 1 calc R . . C9 C 0.69756(15) 0.25998(13) 0.61848(8) 0.02264(19) Uani 1 1 d . . . H9A H 0.6228 0.3134 0.6685 0.027 Uiso 1 1 calc R . . H9B H 0.6788 0.3198 0.5650 0.027 Uiso 1 1 calc R . . C10 C 0.46866(19) 0.1096(2) 0.61626(14) 0.0442(4) Uani 1 1 d . . . H10A H 0.4323 0.0035 0.6166 0.066 Uiso 1 1 calc R . . H10B H 0.4548 0.1716 0.5632 0.066 Uiso 1 1 calc R . . H10C H 0.4020 0.1640 0.6671 0.066 Uiso 1 1 calc R . . C11 C 0.7475(2) 0.01145(16) 0.54100(9) 0.0333(3) Uani 1 1 d . . . H11A H 0.7021 -0.0889 0.5377 0.050 Uiso 1 1 calc R . . H11B H 0.8627 -0.0106 0.5455 0.050 Uiso 1 1 calc R . . H11C H 0.7431 0.0797 0.4886 0.050 Uiso 1 1 calc R . . C12 C 0.66690(19) -0.00512(16) 0.69900(9) 0.0321(3) Uani 1 1 d . . . H12A H 0.6208 -0.1068 0.7000 0.048 Uiso 1 1 calc R . . H12B H 0.6078 0.0516 0.7506 0.048 Uiso 1 1 calc R . . H12C H 0.7847 -0.0250 0.6988 0.048 Uiso 1 1 calc R . . N3 N 0.32782(11) 0.60803(12) 0.81902(6) 0.02028(16) Uani 1 1 d . . . O3 O 0.31039(14) 0.86918(11) 0.84850(7) 0.0336(2) Uani 1 1 d . . . O4 O 0.36943(12) 0.35073(11) 0.78298(6) 0.02737(18) Uani 1 1 d . . . O5 O 0.51510(11) 0.65302(13) 0.65053(6) 0.02873(19) Uani 1 1 d . . . O6 O 0.29873(11) 0.63851(13) 0.59428(6) 0.02883(19) Uani 1 1 d . . . C13 C 0.38363(13) 0.44876(13) 0.83222(7) 0.01984(18) Uani 1 1 d . . . C14 C 0.45867(13) 0.40442(12) 0.90713(6) 0.01860(17) Uani 1 1 d . . . C15 C 0.46787(12) 0.52199(12) 0.96292(6) 0.01665(16) Uani 1 1 d . . . C16 C 0.41281(13) 0.68260(12) 0.94655(6) 0.01836(17) Uani 1 1 d . . . C17 C 0.34710(13) 0.73043(13) 0.86863(7) 0.02107(18) Uani 1 1 d . . . C18 C 0.42062(15) 0.79563(13) 1.00286(7) 0.0232(2) Uani 1 1 d . . . H18 H 0.3817 0.9035 0.9921 0.028 Uiso 1 1 calc R . . C19 C 0.48574(15) 0.75238(13) 1.07613(7) 0.0236(2) Uani 1 1 d . . . H19 H 0.4915 0.8312 1.1141 0.028 Uiso 1 1 calc R . . C20 C 0.24636(13) 0.64736(15) 0.74701(7) 0.0229(2) Uani 1 1 d . . . H20A H 0.1862 0.7549 0.7541 0.028 Uiso 1 1 calc R . . H20B H 0.1635 0.5710 0.7506 0.028 Uiso 1 1 calc R . . C21 C 0.36437(13) 0.64417(13) 0.65681(7) 0.01932(17) Uani 1 1 d . . . O1W O 0.74017(13) 0.57926(13) 0.74928(7) 0.0315(2) Uani 1 1 d D . . H11W H 0.652(2) 0.596(3) 0.7249(15) 0.056(3) Uiso 1 1 d D . . H12W H 0.824(2) 0.624(3) 0.7105(14) 0.056(3) Uiso 1 1 d D . . O2W O 0.75736(12) 0.61768(13) 0.49930(7) 0.03116(19) Uani 1 1 d D . . H21W H 0.672(3) 0.623(3) 0.5466(13) 0.056(3) Uiso 1 1 d D . . H22W H 0.738(3) 0.555(3) 0.4622(13) 0.056(3) Uiso 1 1 d D . . O3W O 0.96390(13) 0.70219(14) 0.60654(8) 0.0366(2) Uani 1 1 d D . . H31W H 0.935(3) 0.662(3) 0.5621(14) 0.056(3) Uiso 1 1 d D . . H32W H 1.072(2) 0.680(3) 0.6020(15) 0.056(3) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0280(4) 0.0281(4) 0.0253(4) -0.0083(3) -0.0155(3) 0.0042(3) N1 0.0259(4) 0.0238(4) 0.0232(4) -0.0062(3) -0.0116(3) 0.0002(3) C1 0.0185(4) 0.0259(5) 0.0197(4) -0.0026(3) -0.0082(3) -0.0018(3) O2 0.0391(5) 0.0323(5) 0.0400(5) -0.0166(4) -0.0197(4) 0.0091(4) N2 0.0238(4) 0.0206(4) 0.0243(4) -0.0047(3) -0.0112(3) -0.0005(3) C2 0.0265(5) 0.0246(5) 0.0254(5) -0.0009(4) -0.0127(4) -0.0020(4) C3 0.0246(5) 0.0263(5) 0.0228(5) 0.0022(4) -0.0114(4) -0.0022(4) C4 0.0190(4) 0.0286(5) 0.0178(4) 0.0003(4) -0.0078(3) -0.0020(3) C5 0.0150(4) 0.0255(4) 0.0166(4) -0.0014(3) -0.0055(3) -0.0028(3) C6 0.0289(5) 0.0223(5) 0.0287(5) -0.0052(4) -0.0155(4) 0.0001(4) C7 0.0237(5) 0.0235(5) 0.0276(5) -0.0053(4) -0.0122(4) -0.0027(4) C8 0.0285(5) 0.0258(5) 0.0214(4) -0.0014(4) -0.0098(4) -0.0063(4) C9 0.0280(5) 0.0178(4) 0.0254(5) -0.0038(3) -0.0133(4) 0.0015(3) C10 0.0270(6) 0.0454(8) 0.0698(11) -0.0180(8) -0.0272(7) 0.0011(5) C11 0.0459(7) 0.0263(5) 0.0284(6) -0.0114(4) -0.0084(5) -0.0003(5) C12 0.0436(7) 0.0293(6) 0.0279(6) 0.0052(4) -0.0144(5) -0.0137(5) N3 0.0201(4) 0.0265(4) 0.0152(3) -0.0007(3) -0.0070(3) -0.0005(3) O3 0.0473(6) 0.0249(4) 0.0321(5) 0.0006(3) -0.0216(4) 0.0070(4) O4 0.0354(4) 0.0299(4) 0.0210(4) -0.0039(3) -0.0118(3) -0.0074(3) O5 0.0183(3) 0.0472(5) 0.0220(4) -0.0006(3) -0.0064(3) -0.0059(3) O6 0.0247(4) 0.0457(5) 0.0189(4) -0.0049(3) -0.0109(3) -0.0005(3) C13 0.0204(4) 0.0245(4) 0.0155(4) -0.0002(3) -0.0052(3) -0.0043(3) C14 0.0212(4) 0.0200(4) 0.0154(4) -0.0012(3) -0.0055(3) -0.0027(3) C15 0.0178(4) 0.0180(4) 0.0145(4) -0.0002(3) -0.0045(3) -0.0018(3) C16 0.0199(4) 0.0194(4) 0.0163(4) -0.0002(3) -0.0061(3) -0.0009(3) C17 0.0219(4) 0.0240(5) 0.0175(4) 0.0000(3) -0.0070(3) 0.0011(3) C18 0.0308(5) 0.0180(4) 0.0223(5) -0.0016(3) -0.0103(4) 0.0009(4) C19 0.0320(5) 0.0205(4) 0.0206(4) -0.0033(3) -0.0101(4) -0.0013(4) C20 0.0175(4) 0.0357(6) 0.0166(4) -0.0003(4) -0.0075(3) -0.0002(4) C21 0.0198(4) 0.0226(4) 0.0166(4) -0.0009(3) -0.0074(3) -0.0001(3) O1W 0.0329(5) 0.0357(5) 0.0295(4) 0.0022(4) -0.0168(4) -0.0001(4) O2W 0.0283(4) 0.0346(5) 0.0306(5) -0.0054(4) -0.0040(3) -0.0070(4) O3W 0.0245(4) 0.0462(6) 0.0413(6) -0.0099(5) -0.0113(4) -0.0001(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.3711(13) . ? O1 C6 1.4253(14) . ? N1 C7 1.3403(15) . ? N1 C8 1.4543(15) . ? N1 H1 0.8800 . ? C1 C2 1.3770(15) . ? C1 C5 1.4297(16) . ? O2 C7 1.2311(15) . ? N2 C11 1.4932(16) . ? N2 C12 1.4961(16) . ? N2 C10 1.5000(17) . ? N2 C9 1.5105(15) . ? C2 C3 1.4182(16) . ? C2 H2 0.9500 . ? C3 C4 1.3668(17) . ? C3 H3 0.9500 . ? C4 C5 1.4217(15) 2_767 ? C4 H4 0.9500 . ? C5 C4 1.4217(15) 2_767 ? C5 C5 1.423(2) 2_767 ? C6 C7 1.5114(16) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C8 C9 1.5199(16) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? N3 C13 1.3921(15) . ? N3 C17 1.4002(15) . ? N3 C20 1.4682(13) . ? O3 C17 1.2167(14) . ? O4 C13 1.2223(13) . ? O5 C21 1.2512(13) . ? O6 C21 1.2553(12) . ? C13 C14 1.4812(14) . ? C14 C19 1.3823(15) 2_667 ? C14 C15 1.4085(14) . ? C15 C16 1.4094(14) . ? C15 C15 1.4185(19) 2_667 ? C16 C18 1.3818(15) . ? C16 C17 1.4841(14) . ? C18 C19 1.4087(16) . ? C18 H18 0.9500 . ? C19 C14 1.3823(15) 2_667 ? C19 H19 0.9500 . ? C20 C21 1.5297(15) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? O1W H11W 0.906(18) . ? O1W H12W 0.905(17) . ? O2W H21W 0.901(17) . ? O2W H22W 0.880(17) . ? O3W H31W 0.904(17) . ? O3W H32W 0.893(17) . ? 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 C1 O1 C6 116.05(9) . . ? C7 N1 C8 121.73(10) . . ? C7 N1 H1 119.1 . . ? C8 N1 H1 119.1 . . ? O1 C1 C2 124.08(10) . . ? O1 C1 C5 114.81(9) . . ? C2 C1 C5 121.11(10) . . ? C11 N2 C12 109.00(10) . . ? C11 N2 C10 108.77(11) . . ? C12 N2 C10 108.58(12) . . ? C11 N2 C9 110.67(10) . . ? C12 N2 C9 112.29(9) . . ? C10 N2 C9 107.44(10) . . ? C1 C2 C3 119.35(11) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 121.76(10) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? C3 C4 C5 119.44(10) . 2_767 ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 2_767 . ? C4 C5 C5 120.26(12) 2_767 2_767 ? C4 C5 C1 121.67(9) 2_767 . ? C5 C5 C1 118.07(12) 2_767 . ? O1 C6 C7 111.22(9) . . ? O1 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? O1 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? O2 C7 N1 124.15(11) . . ? O2 C7 C6 118.34(11) . . ? N1 C7 C6 117.47(10) . . ? N1 C8 C9 114.75(10) . . ? N1 C8 H8A 108.6 . . ? C9 C8 H8A 108.6 . . ? N1 C8 H8B 108.6 . . ? C9 C8 H8B 108.6 . . ? H8A C8 H8B 107.6 . . ? N2 C9 C8 116.63(9) . . ? N2 C9 H9A 108.1 . . ? C8 C9 H9A 108.1 . . ? N2 C9 H9B 108.1 . . ? C8 C9 H9B 108.1 . . ? H9A C9 H9B 107.3 . . ? N2 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 H11A 109.5 . . ? N2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C13 N3 C17 124.30(9) . . ? C13 N3 C20 116.65(9) . . ? C17 N3 C20 119.05(9) . . ? O4 C13 N3 120.03(10) . . ? O4 C13 C14 122.19(10) . . ? N3 C13 C14 117.78(9) . . ? C19 C14 C15 120.17(9) 2_667 . ? C19 C14 C13 120.18(9) 2_667 . ? C15 C14 C13 119.61(9) . . ? C14 C15 C16 120.95(9) . . ? C14 C15 C15 119.56(11) . 2_667 ? C16 C15 C15 119.49(11) . 2_667 ? C18 C16 C15 119.99(9) . . ? C18 C16 C17 120.00(9) . . ? C15 C16 C17 120.00(9) . . ? O3 C17 N3 121.04(10) . . ? O3 C17 C16 122.04(10) . . ? N3 C17 C16 116.92(9) . . ? C16 C18 C19 120.59(10) . . ? C16 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C14 C19 C18 120.19(10) 2_667 . ? C14 C19 H19 119.9 2_667 . ? C18 C19 H19 119.9 . . ? N3 C20 C21 114.35(9) . . ? N3 C20 H20A 108.7 . . ? C21 C20 H20A 108.7 . . ? N3 C20 H20B 108.7 . . ? C21 C20 H20B 108.7 . . ? H20A C20 H20B 107.6 . . ? O5 C21 O6 125.37(10) . . ? O5 C21 C20 118.55(9) . . ? O6 C21 C20 116.03(9) . . ? H11W O1W H12W 105.5(18) . . ? H21W O2W H22W 110.2(18) . . ? H31W O3W H32W 109.9(18) . . ? 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 C6 O1 C1 C2 -12.84(16) . . . . ? C6 O1 C1 C5 166.46(10) . . . . ? O1 C1 C2 C3 178.32(11) . . . . ? C5 C1 C2 C3 -0.94(17) . . . . ? C1 C2 C3 C4 -0.29(18) . . . . ? C2 C3 C4 C5 1.08(17) . . . 2_767 ? O1 C1 C5 C4 1.46(15) . . . 2_767 ? C2 C1 C5 C4 -179.21(11) . . . 2_767 ? O1 C1 C5 C5 -178.00(11) . . . 2_767 ? C2 C1 C5 C5 1.33(18) . . . 2_767 ? C1 O1 C6 C7 -171.62(10) . . . . ? C8 N1 C7 O2 -8.65(19) . . . . ? C8 N1 C7 C6 173.40(10) . . . . ? O1 C6 C7 O2 172.38(12) . . . . ? O1 C6 C7 N1 -9.55(15) . . . . ? C7 N1 C8 C9 119.70(12) . . . . ? C11 N2 C9 C8 -62.44(13) . . . . ? C12 N2 C9 C8 59.61(14) . . . . ? C10 N2 C9 C8 178.94(12) . . . . ? N1 C8 C9 N2 -84.49(13) . . . . ? C17 N3 C13 O4 -176.13(10) . . . . ? C20 N3 C13 O4 2.79(15) . . . . ? C17 N3 C13 C14 4.09(15) . . . . ? C20 N3 C13 C14 -176.98(9) . . . . ? O4 C13 C14 C19 -0.57(17) . . . 2_667 ? N3 C13 C14 C19 179.20(10) . . . 2_667 ? O4 C13 C14 C15 -178.39(10) . . . . ? N3 C13 C14 C15 1.37(15) . . . . ? C19 C14 C15 C16 179.58(10) 2_667 . . . ? C13 C14 C15 C16 -2.60(15) . . . . ? C19 C14 C15 C15 -0.98(18) 2_667 . . 2_667 ? C13 C14 C15 C15 176.85(11) . . . 2_667 ? C14 C15 C16 C18 179.01(10) . . . . ? C15 C15 C16 C18 -0.44(18) 2_667 . . . ? C14 C15 C16 C17 -1.25(15) . . . . ? C15 C15 C16 C17 179.30(11) 2_667 . . . ? C13 N3 C17 O3 172.63(11) . . . . ? C20 N3 C17 O3 -6.27(16) . . . . ? C13 N3 C17 C16 -7.79(15) . . . . ? C20 N3 C17 C16 173.31(9) . . . . ? C18 C16 C17 O3 5.56(18) . . . . ? C15 C16 C17 O3 -174.18(11) . . . . ? C18 C16 C17 N3 -174.02(10) . . . . ? C15 C16 C17 N3 6.24(15) . . . . ? C15 C16 C18 C19 1.00(17) . . . . ? C17 C16 C18 C19 -178.74(11) . . . . ? C16 C18 C19 C14 -0.57(18) . . . 2_667 ? C13 N3 C20 C21 -73.77(13) . . . . ? C17 N3 C20 C21 105.21(12) . . . . ? N3 C20 C21 O5 -19.19(16) . . . . ? N3 C20 C21 O6 163.31(10) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 34.96 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.478 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.064