# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_bo1660 _database_code_depnum_ccdc_archive 'CCDC 885843' #TrackingRef 'BO1660.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H16 N22 O3' _chemical_formula_weight 468.43 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 7.102(2) _cell_length_b 10.781(3) _cell_length_c 12.643(4) _cell_angle_alpha 100.980(5) _cell_angle_beta 100.110(4) _cell_angle_gamma 92.151(3) _cell_volume 932.9(5) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 3373 _cell_measurement_theta_min 2.794 _cell_measurement_theta_max 30.032 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.668 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 0.135 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9318 _exptl_absorpt_correction_T_max 0.9696 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC10/Saturn724+ _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10995 _diffrn_reflns_av_R_equivalents 0.0372 _diffrn_reflns_av_sigmaI/netI 0.0574 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 30.01 _reflns_number_total 5308 _reflns_number_gt 3834 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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 full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0206P)^2^+0.1600P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment X,Y,Z,Ueq _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0311(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5308 _refine_ls_number_parameters 363 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0595 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.0882 _refine_ls_wR_factor_gt 0.0822 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _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 0.58604(15) 0.39252(9) 0.79677(8) 0.0318(3) Uani 1 1 d . . . O2 O 0.53428(14) 0.71272(9) 0.82726(8) 0.0254(2) Uani 1 1 d . . . O3 O 0.66639(16) 0.81934(11) 1.10613(8) 0.0369(3) Uani 1 1 d . . . N1 N 0.62102(17) 0.51359(12) 0.86026(10) 0.0284(3) Uani 1 1 d . . . N2 N 0.47349(17) 0.39342(11) 0.69577(10) 0.0265(3) Uani 1 1 d . . . N3 N 0.26316(16) 0.46835(10) 0.50617(9) 0.0216(2) Uani 1 1 d . . . N4 N 0.17065(16) 0.54023(10) 0.44153(9) 0.0223(2) Uani 1 1 d . . . N5 N 0.17710(16) 0.65792(10) 0.49611(9) 0.0215(2) Uani 1 1 d . . . N6 N 0.27530(16) 0.66680(10) 0.59910(9) 0.0207(2) Uani 1 1 d . . . N7 N 0.59392(19) 0.72285(13) 1.01830(10) 0.0333(3) Uani 1 1 d . . . N8 N 0.71867(18) 0.92795(12) 1.07177(10) 0.0310(3) Uani 1 1 d . . . N9 N 0.79372(18) 1.10807(11) 0.94056(11) 0.0322(3) Uani 1 1 d . . . N10 N 0.81663(19) 1.15677(12) 0.85335(12) 0.0357(3) Uani 1 1 d . . . N11 N 0.76374(19) 1.07013(11) 0.76258(11) 0.0323(3) Uani 1 1 d . . . N12 N 0.70295(17) 0.96168(11) 0.78875(10) 0.0259(3) Uani 1 1 d . . . N13 N 0.02108(17) 0.14321(12) 0.60306(10) 0.0234(3) Uani 1 1 d . . . N14 N 0.29536(17) 0.03568(11) 0.60288(10) 0.0222(2) Uani 1 1 d . . . N15 N 0.22998(18) -0.04058(12) 0.67001(11) 0.0246(3) Uani 1 1 d . . . N16 N 0.23623(16) 0.18471(11) 0.49561(10) 0.0223(3) Uani 1 1 d . . . N17 N 0.42088(18) 0.16645(13) 0.47052(12) 0.0290(3) Uani 1 1 d . . . N18 N -0.16419(19) 0.40209(13) 0.03864(11) 0.0295(3) Uani 1 1 d . . . N19 N -0.02636(18) 0.27685(11) 0.15399(10) 0.0250(3) Uani 1 1 d . . . N20 N 0.0596(2) 0.26841(12) 0.26157(10) 0.0265(3) Uani 1 1 d . . . N21 N -0.02623(17) 0.49191(10) 0.21614(10) 0.0219(2) Uani 1 1 d . . . N22 N -0.06848(19) 0.61019(11) 0.18944(11) 0.0262(3) Uani 1 1 d . . . C1 C 0.53296(18) 0.58488(12) 0.79924(11) 0.0206(3) Uani 1 1 d . . . C2 C 0.43902(18) 0.51164(12) 0.69577(11) 0.0191(3) Uani 1 1 d . . . C3 C 0.32592(17) 0.54902(12) 0.60145(11) 0.0176(3) Uani 1 1 d . . . C4 C 0.60273(19) 0.77196(13) 0.93356(11) 0.0224(3) Uani 1 1 d . . . C5 C 0.68122(18) 0.89967(13) 0.96465(11) 0.0220(3) Uani 1 1 d . . . C6 C 0.72365(18) 0.98901(12) 0.89764(11) 0.0224(3) Uani 1 1 d . . . C7 C 0.18378(18) 0.12060(12) 0.56822(10) 0.0188(3) Uani 1 1 d . . . C8 C -0.07221(18) 0.39095(12) 0.13586(11) 0.0203(3) Uani 1 1 d . . . H13A H -0.019(2) 0.0990(16) 0.6481(14) 0.033(5) Uiso 1 1 d . . . H13B H -0.057(2) 0.1983(16) 0.5759(13) 0.033(4) Uiso 1 1 d . . . H14 H 0.405(3) 0.0235(17) 0.5751(14) 0.045(5) Uiso 1 1 d . . . H15A H 0.253(2) -0.1253(17) 0.6430(14) 0.042(5) Uiso 1 1 d . . . H15B H 0.300(3) -0.0175(17) 0.7401(15) 0.045(5) Uiso 1 1 d . . . H16 H 0.197(2) 0.2589(16) 0.4941(13) 0.030(4) Uiso 1 1 d . . . H17A H 0.412(3) 0.1657(17) 0.3950(16) 0.046(5) Uiso 1 1 d . . . H17B H 0.498(3) 0.235(2) 0.5101(17) 0.064(7) Uiso 1 1 d . . . H18A H -0.191(2) 0.4779(17) 0.0304(14) 0.041(5) Uiso 1 1 d . . . H18B H -0.193(3) 0.3339(17) -0.0140(15) 0.044(5) Uiso 1 1 d . . . H19 H -0.082(2) 0.2121(16) 0.1073(14) 0.034(5) Uiso 1 1 d . . . H20A H 0.144(3) 0.2031(18) 0.2550(14) 0.047(5) Uiso 1 1 d . . . H20B H -0.037(3) 0.2444(19) 0.2943(16) 0.061(6) Uiso 1 1 d . . . H21 H 0.037(2) 0.4855(16) 0.2841(14) 0.039(5) Uiso 1 1 d . . . H22A H 0.042(3) 0.6619(16) 0.1930(14) 0.039(5) Uiso 1 1 d . . . H22B H -0.131(3) 0.6514(16) 0.2398(14) 0.040(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0394(6) 0.0255(5) 0.0297(6) 0.0101(5) -0.0023(5) 0.0084(4) O2 0.0344(5) 0.0192(5) 0.0183(5) 0.0030(4) -0.0043(4) -0.0042(4) O3 0.0473(7) 0.0443(7) 0.0175(5) 0.0043(5) 0.0038(5) 0.0016(5) N1 0.0294(6) 0.0275(6) 0.0268(7) 0.0078(5) -0.0018(5) 0.0021(5) N2 0.0323(7) 0.0233(6) 0.0239(6) 0.0078(5) 0.0007(5) 0.0063(5) N3 0.0248(6) 0.0187(6) 0.0201(6) 0.0032(5) 0.0013(5) 0.0031(4) N4 0.0264(6) 0.0196(6) 0.0198(6) 0.0039(5) 0.0007(5) 0.0028(4) N5 0.0248(6) 0.0191(6) 0.0196(6) 0.0036(5) 0.0015(5) 0.0020(4) N6 0.0245(6) 0.0170(5) 0.0199(6) 0.0038(4) 0.0021(4) 0.0022(4) N7 0.0380(7) 0.0383(8) 0.0210(7) 0.0055(6) 0.0007(5) -0.0038(6) N8 0.0364(7) 0.0330(7) 0.0209(7) 0.0005(5) 0.0033(5) 0.0042(5) N9 0.0339(7) 0.0209(6) 0.0370(8) -0.0035(6) 0.0044(6) -0.0014(5) N10 0.0369(7) 0.0184(6) 0.0501(9) 0.0033(6) 0.0078(6) -0.0008(5) N11 0.0381(7) 0.0218(6) 0.0394(8) 0.0093(6) 0.0103(6) 0.0023(5) N12 0.0346(7) 0.0177(6) 0.0252(6) 0.0040(5) 0.0058(5) 0.0006(5) N13 0.0259(6) 0.0231(6) 0.0237(7) 0.0078(5) 0.0069(5) 0.0072(5) N14 0.0243(6) 0.0190(6) 0.0253(6) 0.0083(5) 0.0056(5) 0.0039(4) N15 0.0349(7) 0.0189(6) 0.0210(6) 0.0057(5) 0.0056(5) 0.0034(5) N16 0.0234(6) 0.0178(6) 0.0280(7) 0.0078(5) 0.0066(5) 0.0047(4) N17 0.0261(6) 0.0297(7) 0.0352(8) 0.0105(6) 0.0120(6) 0.0044(5) N18 0.0393(7) 0.0219(7) 0.0218(7) 0.0011(6) -0.0055(5) 0.0013(5) N19 0.0344(7) 0.0176(6) 0.0198(6) 0.0012(5) -0.0003(5) 0.0013(5) N20 0.0357(7) 0.0259(6) 0.0198(6) 0.0064(5) 0.0065(5) 0.0086(5) N21 0.0298(6) 0.0168(5) 0.0179(6) 0.0021(5) 0.0022(5) 0.0028(4) N22 0.0339(7) 0.0165(6) 0.0283(7) 0.0042(5) 0.0057(5) 0.0036(5) C1 0.0191(6) 0.0212(7) 0.0215(7) 0.0074(5) 0.0014(5) -0.0008(5) C2 0.0198(6) 0.0184(6) 0.0208(7) 0.0061(5) 0.0055(5) 0.0016(5) C3 0.0183(6) 0.0162(6) 0.0187(6) 0.0042(5) 0.0039(5) 0.0011(4) C4 0.0233(7) 0.0268(7) 0.0157(7) 0.0037(6) 0.0008(5) -0.0003(5) C5 0.0200(6) 0.0243(7) 0.0184(7) -0.0014(5) 0.0011(5) 0.0018(5) C6 0.0213(6) 0.0182(6) 0.0244(7) -0.0026(5) 0.0030(5) 0.0014(5) C7 0.0227(6) 0.0142(6) 0.0165(6) -0.0007(5) 0.0002(5) 0.0004(5) C8 0.0212(6) 0.0201(6) 0.0186(7) 0.0020(5) 0.0036(5) -0.0006(5) _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 N1 1.3843(16) . ? O1 N2 1.3843(15) . ? O2 C1 1.3554(16) . ? O2 C4 1.3677(16) . ? O3 N7 1.3781(17) . ? O3 N8 1.3840(17) . ? N1 C1 1.2921(17) . ? N2 C2 1.3067(17) . ? N3 C3 1.3376(17) . ? N3 N4 1.3382(15) . ? N4 N5 1.3187(15) . ? N5 N6 1.3490(15) . ? N6 C3 1.3368(16) . ? N7 C4 1.2920(18) . ? N8 C5 1.3069(18) . ? N9 C6 1.3348(18) . ? N9 N10 1.3397(19) . ? N10 N11 1.3208(18) . ? N11 N12 1.3499(17) . ? N12 C6 1.3323(18) . ? N13 C7 1.3219(17) . ? N13 H13A 0.884(17) . ? N13 H13B 0.901(16) . ? N14 C7 1.3204(16) . ? N14 N15 1.4096(17) . ? N14 H14 0.913(18) . ? N15 H15A 0.944(18) . ? N15 H15B 0.921(18) . ? N16 C7 1.3423(18) . ? N16 N17 1.4143(16) . ? N16 H16 0.860(16) . ? N17 H17A 0.944(19) . ? N17 H17B 0.91(2) . ? N18 C8 1.3160(18) . ? N18 H18A 0.867(18) . ? N18 H18B 0.883(19) . ? N19 C8 1.3353(17) . ? N19 N20 1.4108(17) . ? N19 H19 0.855(17) . ? N20 H20A 0.941(19) . ? N20 H20B 0.92(2) . ? N21 C8 1.3257(17) . ? N21 N22 1.4096(16) . ? N21 H21 0.912(17) . ? N22 H22A 0.935(18) . ? N22 H22B 0.898(18) . ? C1 C2 1.4285(19) . ? C2 C3 1.4494(18) . ? C4 C5 1.4213(19) . ? C5 C6 1.454(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 N1 O1 N2 111.02(9) . . ? C1 O2 C4 119.29(10) . . ? N7 O3 N8 111.37(10) . . ? C1 N1 O1 104.51(11) . . ? C2 N2 O1 106.10(11) . . ? C3 N3 N4 104.05(11) . . ? N5 N4 N3 109.91(10) . . ? N4 N5 N6 109.58(10) . . ? C3 N6 N5 103.74(10) . . ? C4 N7 O3 104.12(12) . . ? C5 N8 O3 105.83(12) . . ? C6 N9 N10 104.08(12) . . ? N11 N10 N9 110.01(12) . . ? N10 N11 N12 109.02(12) . . ? C6 N12 N11 104.24(11) . . ? C7 N13 H13A 120.6(11) . . ? C7 N13 H13B 120.3(11) . . ? H13A N13 H13B 118.8(15) . . ? C7 N14 N15 118.90(12) . . ? C7 N14 H14 117.3(11) . . ? N15 N14 H14 123.4(11) . . ? N14 N15 H15A 108.2(11) . . ? N14 N15 H15B 109.4(11) . . ? H15A N15 H15B 107.2(14) . . ? C7 N16 N17 116.65(11) . . ? C7 N16 H16 119.1(11) . . ? N17 N16 H16 115.5(11) . . ? N16 N17 H17A 107.4(11) . . ? N16 N17 H17B 106.4(13) . . ? H17A N17 H17B 109.4(17) . . ? C8 N18 H18A 116.7(12) . . ? C8 N18 H18B 119.3(11) . . ? H18A N18 H18B 124.0(16) . . ? C8 N19 N20 117.57(12) . . ? C8 N19 H19 117.5(11) . . ? N20 N19 H19 121.9(11) . . ? N19 N20 H20A 106.6(11) . . ? N19 N20 H20B 106.4(12) . . ? H20A N20 H20B 108.7(16) . . ? C8 N21 N22 116.72(12) . . ? C8 N21 H21 121.5(11) . . ? N22 N21 H21 121.7(11) . . ? N21 N22 H22A 112.5(10) . . ? N21 N22 H22B 108.0(11) . . ? H22A N22 H22B 106.0(15) . . ? N1 C1 O2 124.95(12) . . ? N1 C1 C2 111.01(12) . . ? O2 C1 C2 124.00(11) . . ? N2 C2 C1 107.36(11) . . ? N2 C2 C3 121.54(12) . . ? C1 C2 C3 131.10(12) . . ? N6 C3 N3 112.72(11) . . ? N6 C3 C2 124.26(12) . . ? N3 C3 C2 123.01(11) . . ? N7 C4 O2 124.90(13) . . ? N7 C4 C5 111.41(12) . . ? O2 C4 C5 123.56(12) . . ? N8 C5 C4 107.27(13) . . ? N8 C5 C6 122.38(13) . . ? C4 C5 C6 130.32(12) . . ? N12 C6 N9 112.64(13) . . ? N12 C6 C5 124.69(12) . . ? N9 C6 C5 122.64(13) . . ? N14 C7 N13 121.37(13) . . ? N14 C7 N16 119.27(12) . . ? N13 C7 N16 119.36(12) . . ? N18 C8 N21 120.54(13) . . ? N18 C8 N19 119.69(13) . . ? N21 C8 N19 119.77(12) . . ? 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 N2 O1 N1 C1 -0.22(15) . . . . ? N1 O1 N2 C2 0.09(15) . . . . ? C3 N3 N4 N5 -0.39(14) . . . . ? N3 N4 N5 N6 0.11(15) . . . . ? N4 N5 N6 C3 0.22(14) . . . . ? N8 O3 N7 C4 0.12(16) . . . . ? N7 O3 N8 C5 -0.52(15) . . . . ? C6 N9 N10 N11 -0.42(16) . . . . ? N9 N10 N11 N12 0.45(16) . . . . ? N10 N11 N12 C6 -0.27(15) . . . . ? O1 N1 C1 O2 -177.52(12) . . . . ? O1 N1 C1 C2 0.26(15) . . . . ? C4 O2 C1 N1 -12.4(2) . . . . ? C4 O2 C1 C2 170.08(12) . . . . ? O1 N2 C2 C1 0.07(14) . . . . ? O1 N2 C2 C3 179.21(11) . . . . ? N1 C1 C2 N2 -0.22(16) . . . . ? O2 C1 C2 N2 177.59(12) . . . . ? N1 C1 C2 C3 -179.25(13) . . . . ? O2 C1 C2 C3 -1.4(2) . . . . ? N5 N6 C3 N3 -0.49(14) . . . . ? N5 N6 C3 C2 178.60(12) . . . . ? N4 N3 C3 N6 0.55(15) . . . . ? N4 N3 C3 C2 -178.55(12) . . . . ? N2 C2 C3 N6 175.40(13) . . . . ? C1 C2 C3 N6 -5.7(2) . . . . ? N2 C2 C3 N3 -5.6(2) . . . . ? C1 C2 C3 N3 173.32(13) . . . . ? O3 N7 C4 O2 -175.65(12) . . . . ? O3 N7 C4 C5 0.30(16) . . . . ? C1 O2 C4 N7 -30.3(2) . . . . ? C1 O2 C4 C5 154.19(13) . . . . ? O3 N8 C5 C4 0.67(14) . . . . ? O3 N8 C5 C6 -177.67(12) . . . . ? N7 C4 C5 N8 -0.65(17) . . . . ? O2 C4 C5 N8 175.37(12) . . . . ? N7 C4 C5 C6 177.51(13) . . . . ? O2 C4 C5 C6 -6.5(2) . . . . ? N11 N12 C6 N9 0.00(15) . . . . ? N11 N12 C6 C5 -178.22(12) . . . . ? N10 N9 C6 N12 0.25(16) . . . . ? N10 N9 C6 C5 178.52(12) . . . . ? N8 C5 C6 N12 174.24(13) . . . . ? C4 C5 C6 N12 -3.7(2) . . . . ? N8 C5 C6 N9 -3.8(2) . . . . ? C4 C5 C6 N9 178.27(14) . . . . ? N15 N14 C7 N13 6.21(19) . . . . ? N15 N14 C7 N16 -173.40(12) . . . . ? N17 N16 C7 N14 -7.01(18) . . . . ? N17 N16 C7 N13 173.37(13) . . . . ? N22 N21 C8 N18 -4.3(2) . . . . ? N22 N21 C8 N19 176.24(12) . . . . ? N20 N19 C8 N18 -175.46(13) . . . . ? N20 N19 C8 N21 3.95(19) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.273 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.051 data_bo1725 _database_code_depnum_ccdc_archive 'CCDC 885844' #TrackingRef 'BO1725.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H18 N28 O11' _chemical_formula_weight 742.55 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 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 12.2118(10) _cell_length_b 9.2324(5) _cell_length_c 13.7527(14) _cell_angle_alpha 90.00 _cell_angle_beta 114.505(4) _cell_angle_gamma 90.00 _cell_volume 1410.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 5494 _cell_measurement_theta_min 2.206 _cell_measurement_theta_max 30.031 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.748 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.151 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC10/Saturn724+ _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12901 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0405 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 30.07 _reflns_number_total 4217 _reflns_number_gt 3653 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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 full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0395P)^2^+0.1690P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 4217 _refine_ls_number_parameters 509 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0442 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0866 _refine_ls_wR_factor_gt 0.0829 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 1.40807(15) 0.2687(2) 0.66514(13) 0.0283(4) Uani 1 1 d . . . O2 O 1.16498(14) 0.1432(2) 0.44684(12) 0.0240(4) Uani 1 1 d . . . O3 O 1.15374(14) 0.27624(19) 0.20986(12) 0.0247(4) Uani 1 1 d . . . O4 O 0.91416(15) 0.2551(2) 0.65366(13) 0.0293(4) Uani 1 1 d . . . O5 O 0.65279(15) 0.1477(2) 0.44704(12) 0.0274(4) Uani 1 1 d . . . O6 O 0.63719(15) 0.2569(2) 0.20329(13) 0.0282(4) Uani 1 1 d . . . O7 O 0.42883(14) 0.60424(17) 0.03619(13) 0.0210(3) Uani 1 1 d . . . O8 O 0.04571(14) 0.83298(19) 0.06798(13) 0.0242(3) Uani 1 1 d . . . H8A H 0.0336 0.8996 0.0226 0.029 Uiso 1 1 d R . . H8B H 0.1028 0.8535 0.1249 0.029 Uiso 1 1 d R . . O9 O 0.68898(13) 0.57202(19) 0.04567(13) 0.0221(3) Uani 1 1 d . . . H9A H 0.7407 0.5531 0.1101 0.027 Uiso 1 1 d R . . H9B H 0.7268 0.6238 0.0185 0.027 Uiso 1 1 d R . . O10 O 0.22187(18) 0.3185(3) 0.02638(16) 0.0414(5) Uani 1 1 d . . . H10A H 0.2292 0.3115 0.0918 0.050 Uiso 1 1 d R . . H10B H 0.1460 0.3089 -0.0140 0.050 Uiso 1 1 d R . . O11 O 0.96940(19) 0.5374(2) 0.07820(15) 0.0436(5) Uani 1 1 d . . . H11A H 0.9859 0.6269 0.0839 0.052 Uiso 1 1 d R . . H11B H 0.9833 0.5030 0.1388 0.052 Uiso 1 1 d R . . N1 N 1.34787(18) 0.2641(2) 0.55408(15) 0.0259(4) Uani 1 1 d . . . N2 N 1.34738(17) 0.1930(2) 0.71391(15) 0.0233(4) Uani 1 1 d . . . N3 N 1.15568(17) 0.0257(2) 0.74194(15) 0.0234(4) Uani 1 1 d . . . N4 N 1.05138(19) -0.0475(2) 0.71688(17) 0.0270(4) Uani 1 1 d . . . N5 N 0.99262(18) -0.0580(2) 0.61398(16) 0.0259(4) Uani 1 1 d . . . N6 N 1.05837(16) 0.0093(2) 0.57036(16) 0.0200(4) Uani 1 1 d . . . N7 N 1.21657(17) 0.2673(2) 0.32056(15) 0.0226(4) Uani 1 1 d . . . N8 N 1.04694(17) 0.1995(2) 0.17391(15) 0.0228(4) Uani 1 1 d . . . N9 N 0.84572(17) 0.0235(2) 0.17409(15) 0.0216(4) Uani 1 1 d . . . N10 N 0.77755(17) -0.0502(2) 0.21293(16) 0.0240(4) Uani 1 1 d . . . N11 N 0.83074(17) -0.0545(2) 0.31784(16) 0.0233(4) Uani 1 1 d . . . N12 N 0.93610(16) 0.0161(2) 0.35102(14) 0.0196(4) Uani 1 1 d . . . N13 N 0.84481(18) 0.2536(3) 0.54358(16) 0.0272(4) Uani 1 1 d . . . N14 N 0.85706(18) 0.1861(2) 0.70854(16) 0.0253(4) Uani 1 1 d . . . N15 N 0.66579(17) 0.0372(2) 0.75216(15) 0.0222(4) Uani 1 1 d . . . N16 N 0.56283(19) -0.0372(2) 0.73249(16) 0.0272(5) Uani 1 1 d . . . N17 N 0.49973(18) -0.0509(2) 0.63048(17) 0.0266(4) Uani 1 1 d . . . N18 N 0.56123(17) 0.0146(2) 0.58155(15) 0.0196(4) Uani 1 1 d . . . N19 N 0.70155(17) 0.2552(2) 0.31325(15) 0.0234(4) Uani 1 1 d . . . N20 N 0.52921(18) 0.1830(2) 0.17235(15) 0.0256(4) Uani 1 1 d . . . N21 N 0.32571(17) 0.0170(2) 0.18611(15) 0.0245(4) Uani 1 1 d . . . N22 N 0.26271(17) -0.0532(2) 0.23239(16) 0.0249(4) Uani 1 1 d . . . N23 N 0.32413(17) -0.0548(2) 0.33646(16) 0.0238(4) Uani 1 1 d . . . N24 N 0.42868(16) 0.0146(2) 0.36195(14) 0.0194(4) Uani 1 1 d . . . N25 N 0.46590(17) 0.8479(2) 0.05298(16) 0.0209(4) Uani 1 1 d . . . N26 N 0.57816(17) 0.8267(2) 0.04774(17) 0.0191(4) Uani 1 1 d . . . N27 N 0.28232(17) 0.7644(2) 0.02733(16) 0.0216(4) Uani 1 1 d . . . N28 N 0.21059(17) 0.6447(2) 0.03128(16) 0.0193(4) Uani 1 1 d . . . C1 C 1.25455(19) 0.1863(3) 0.53869(17) 0.0192(4) Uani 1 1 d . . . C2 C 1.25183(19) 0.1417(2) 0.63606(17) 0.0180(4) Uani 1 1 d . . . C3 C 1.15775(19) 0.0596(2) 0.65005(17) 0.0172(4) Uani 1 1 d . . . C4 C 1.1475(2) 0.1880(2) 0.34844(17) 0.0186(4) Uani 1 1 d . . . C5 C 1.04171(19) 0.1459(2) 0.25941(17) 0.0175(4) Uani 1 1 d . . . C6 C 0.94193(18) 0.0625(2) 0.26114(17) 0.0168(4) Uani 1 1 d . . . C7 C 0.74942(19) 0.1842(3) 0.53473(17) 0.0198(4) Uani 1 1 d . . . C8 C 0.75437(19) 0.1422(2) 0.63532(17) 0.0180(4) Uani 1 1 d . . . C9 C 0.66248(19) 0.0675(2) 0.65663(17) 0.0173(4) Uani 1 1 d . . . C10 C 0.6332(2) 0.1826(2) 0.34579(17) 0.0199(4) Uani 1 1 d . . . C11 C 0.52548(19) 0.1366(2) 0.26002(17) 0.0188(4) Uani 1 1 d . . . C12 C 0.42697(19) 0.0565(2) 0.26827(17) 0.0181(4) Uani 1 1 d . . . C13 C 0.39612(19) 0.7282(2) 0.03856(17) 0.0171(4) Uani 1 1 d . . . H6 H 1.027(3) 0.013(4) 0.496(3) 0.059(11) Uiso 1 1 d . . . H18 H 0.527(3) 0.014(4) 0.503(3) 0.058(11) Uiso 1 1 d . . . H25 H 0.428(3) 0.933(3) 0.024(2) 0.034(8) Uiso 1 1 d . . . H27 H 0.284(3) 0.840(4) 0.059(2) 0.047(10) Uiso 1 1 d . . . H26B H 0.641(2) 0.862(3) 0.116(2) 0.028(7) Uiso 1 1 d . . . H26C H 0.578(3) 0.873(4) -0.012(2) 0.038(9) Uiso 1 1 d . . . H28A H 0.245(2) 0.592(3) 0.097(2) 0.029(7) Uiso 1 1 d . . . H286 H 0.595(2) 0.723(4) 0.045(2) 0.027(7) Uiso 1 1 d . . . H28B H 0.131(3) 0.677(4) 0.030(3) 0.061(11) Uiso 1 1 d . . . H28C H 0.197(2) 0.589(3) -0.034(2) 0.023(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0235(8) 0.0355(10) 0.0215(9) -0.0024(8) 0.0051(7) -0.0115(7) O2 0.0219(8) 0.0317(9) 0.0146(8) 0.0019(7) 0.0038(6) -0.0112(7) O3 0.0268(8) 0.0297(9) 0.0191(8) 0.0023(7) 0.0111(7) -0.0062(7) O4 0.0236(8) 0.0381(10) 0.0211(9) -0.0017(8) 0.0043(7) -0.0113(8) O5 0.0236(8) 0.0421(11) 0.0116(8) 0.0028(7) 0.0024(6) -0.0123(8) O6 0.0295(9) 0.0389(10) 0.0178(8) 0.0030(8) 0.0113(7) -0.0040(8) O7 0.0212(8) 0.0161(7) 0.0268(9) -0.0015(6) 0.0113(7) -0.0014(6) O8 0.0244(8) 0.0266(9) 0.0176(8) 0.0002(7) 0.0046(7) -0.0030(7) O9 0.0193(8) 0.0230(8) 0.0215(8) -0.0004(7) 0.0060(6) -0.0007(6) O10 0.0438(11) 0.0490(13) 0.0358(11) 0.0048(10) 0.0210(9) 0.0046(10) O11 0.0727(14) 0.0308(11) 0.0296(10) -0.0068(8) 0.0235(10) -0.0118(10) N1 0.0236(10) 0.0317(11) 0.0189(10) -0.0010(9) 0.0054(8) -0.0084(9) N2 0.0240(10) 0.0236(10) 0.0218(10) -0.0014(8) 0.0089(8) -0.0040(8) N3 0.0258(10) 0.0237(10) 0.0204(10) 0.0021(8) 0.0092(8) -0.0018(8) N4 0.0285(11) 0.0317(11) 0.0225(11) 0.0022(9) 0.0122(9) -0.0065(9) N5 0.0280(10) 0.0291(11) 0.0233(10) -0.0002(9) 0.0134(9) -0.0085(9) N6 0.0197(9) 0.0234(10) 0.0172(10) -0.0007(8) 0.0079(8) -0.0043(7) N7 0.0232(9) 0.0238(10) 0.0213(10) 0.0021(8) 0.0098(8) -0.0023(8) N8 0.0223(10) 0.0240(10) 0.0231(10) 0.0020(8) 0.0105(8) -0.0012(8) N9 0.0205(9) 0.0223(10) 0.0187(10) -0.0006(8) 0.0048(8) -0.0032(7) N10 0.0215(9) 0.0257(10) 0.0214(10) -0.0003(9) 0.0056(8) -0.0046(8) N11 0.0190(9) 0.0264(10) 0.0212(10) -0.0017(8) 0.0050(8) -0.0063(8) N12 0.0177(9) 0.0220(9) 0.0173(9) 0.0003(8) 0.0055(8) -0.0031(7) N13 0.0239(10) 0.0344(12) 0.0201(10) 0.0002(9) 0.0058(8) -0.0076(9) N14 0.0250(10) 0.0277(11) 0.0212(10) -0.0005(8) 0.0077(8) -0.0029(8) N15 0.0282(10) 0.0210(10) 0.0178(9) 0.0004(8) 0.0101(8) 0.0002(8) N16 0.0328(11) 0.0287(11) 0.0230(11) -0.0011(9) 0.0144(9) -0.0048(9) N17 0.0291(10) 0.0287(11) 0.0250(11) 0.0007(9) 0.0142(9) -0.0062(9) N18 0.0204(9) 0.0208(9) 0.0171(10) 0.0009(8) 0.0074(8) -0.0016(7) N19 0.0264(10) 0.0264(10) 0.0178(10) 0.0027(8) 0.0096(8) -0.0009(8) N20 0.0260(10) 0.0321(12) 0.0185(10) -0.0007(8) 0.0089(8) -0.0016(8) N21 0.0198(9) 0.0325(11) 0.0194(10) -0.0047(9) 0.0064(8) -0.0009(8) N22 0.0221(10) 0.0281(11) 0.0233(11) -0.0057(9) 0.0083(8) -0.0049(8) N23 0.0199(9) 0.0253(10) 0.0226(10) -0.0034(8) 0.0051(8) -0.0045(8) N24 0.0176(9) 0.0211(9) 0.0162(9) -0.0005(7) 0.0036(7) -0.0022(7) N25 0.0194(9) 0.0144(9) 0.0272(11) -0.0003(8) 0.0079(8) 0.0002(7) N26 0.0171(9) 0.0170(9) 0.0215(10) -0.0015(8) 0.0063(8) -0.0026(7) N27 0.0198(9) 0.0164(9) 0.0283(11) -0.0056(8) 0.0097(8) -0.0035(7) N28 0.0165(9) 0.0206(9) 0.0198(10) 0.0006(8) 0.0065(8) -0.0006(7) C1 0.0165(10) 0.0212(11) 0.0172(11) -0.0007(8) 0.0044(9) -0.0018(8) C2 0.0178(10) 0.0154(9) 0.0188(11) -0.0002(8) 0.0056(8) 0.0013(8) C3 0.0182(10) 0.0163(10) 0.0152(10) 0.0000(8) 0.0050(8) 0.0016(8) C4 0.0211(10) 0.0172(10) 0.0189(11) 0.0000(8) 0.0098(9) -0.0012(8) C5 0.0190(10) 0.0168(10) 0.0170(10) -0.0007(8) 0.0076(8) -0.0001(8) C6 0.0165(10) 0.0160(10) 0.0152(10) 0.0009(8) 0.0036(8) 0.0020(8) C7 0.0176(10) 0.0222(11) 0.0164(11) -0.0002(9) 0.0040(9) -0.0022(8) C8 0.0196(10) 0.0168(10) 0.0156(10) -0.0004(8) 0.0052(8) 0.0014(8) C9 0.0201(10) 0.0145(9) 0.0158(10) 0.0001(8) 0.0058(9) 0.0025(8) C10 0.0226(11) 0.0208(11) 0.0168(11) 0.0015(8) 0.0088(9) 0.0002(9) C11 0.0190(10) 0.0208(10) 0.0145(10) -0.0009(8) 0.0048(9) 0.0026(8) C12 0.0187(10) 0.0178(10) 0.0166(11) -0.0021(8) 0.0062(9) 0.0020(8) C13 0.0175(10) 0.0192(10) 0.0134(10) -0.0026(8) 0.0052(8) -0.0013(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 O1 N2 1.378(2) . ? O1 N1 1.394(2) . ? O2 C1 1.343(3) . ? O2 C4 1.345(3) . ? O3 N8 1.383(2) . ? O3 N7 1.394(2) . ? O4 N14 1.378(2) . ? O4 N13 1.395(3) . ? O5 C7 1.334(3) . ? O5 C10 1.350(3) . ? O6 N19 1.385(2) . ? O6 N20 1.386(3) . ? O7 C13 1.217(3) . ? O8 H8A 0.8446 . ? O8 H8B 0.8254 . ? O9 H9A 0.8661 . ? O9 H9B 0.8513 . ? O10 H10A 0.8684 . ? O10 H10B 0.8652 . ? O11 H11A 0.8465 . ? O11 H11B 0.8403 . ? N1 C1 1.288(3) . ? N2 C2 1.302(3) . ? N3 C3 1.312(3) . ? N3 N4 1.354(3) . ? N4 N5 1.298(3) . ? N5 N6 1.338(3) . ? N6 C3 1.336(3) . ? N6 H6 0.94(4) . ? N7 C4 1.289(3) . ? N8 C5 1.302(3) . ? N9 C6 1.333(3) . ? N9 N10 1.346(3) . ? N10 N11 1.314(3) . ? N11 N12 1.342(2) . ? N12 C6 1.338(3) . ? N13 C7 1.291(3) . ? N14 C8 1.305(3) . ? N15 C9 1.327(3) . ? N15 N16 1.358(3) . ? N16 N17 1.297(3) . ? N17 N18 1.342(3) . ? N18 C9 1.332(3) . ? N18 H18 0.98(4) . ? N19 C10 1.287(3) . ? N20 C11 1.298(3) . ? N21 C12 1.334(3) . ? N21 N22 1.350(3) . ? N22 N23 1.312(3) . ? N23 N24 1.339(3) . ? N24 C12 1.337(3) . ? N25 C13 1.359(3) . ? N25 N26 1.416(3) . ? N25 H25 0.92(3) . ? N26 H26B 0.99(3) . ? N26 H26C 0.93(3) . ? N26 H286 0.98(3) . ? N27 C13 1.374(3) . ? N27 N28 1.426(3) . ? N27 H27 0.82(4) . ? N28 H28A 0.95(3) . ? N28 H28B 1.01(4) . ? N28 H28C 0.98(3) . ? C1 C2 1.415(3) . ? C2 C3 1.454(3) . ? C4 C5 1.417(3) . ? C5 C6 1.450(3) . ? C7 C8 1.414(3) . ? C8 C9 1.447(3) . ? C10 C11 1.419(3) . ? C11 C12 1.456(3) . ? 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 N2 O1 N1 111.86(16) . . ? C1 O2 C4 125.63(18) . . ? N8 O3 N7 111.72(15) . . ? N14 O4 N13 111.89(16) . . ? C7 O5 C10 125.73(19) . . ? N19 O6 N20 111.49(16) . . ? H8A O8 H8B 110.7 . . ? H9A O9 H9B 105.3 . . ? H10A O10 H10B 106.2 . . ? H11A O11 H11B 109.6 . . ? C1 N1 O1 103.02(18) . . ? C2 N2 O1 105.29(18) . . ? C3 N3 N4 105.41(19) . . ? N5 N4 N3 110.55(18) . . ? N4 N5 N6 106.92(19) . . ? C3 N6 N5 107.66(19) . . ? C3 N6 H6 135(2) . . ? N5 N6 H6 118(2) . . ? C4 N7 O3 103.11(17) . . ? C5 N8 O3 105.33(17) . . ? C6 N9 N10 103.88(18) . . ? N11 N10 N9 110.22(18) . . ? N10 N11 N12 109.04(18) . . ? C6 N12 N11 104.61(17) . . ? C7 N13 O4 103.00(18) . . ? C8 N14 O4 105.28(18) . . ? C9 N15 N16 105.29(18) . . ? N17 N16 N15 110.53(18) . . ? N16 N17 N18 107.06(19) . . ? C9 N18 N17 108.00(19) . . ? C9 N18 H18 133(2) . . ? N17 N18 H18 119(2) . . ? C10 N19 O6 103.26(18) . . ? C11 N20 O6 105.83(17) . . ? C12 N21 N22 103.97(19) . . ? N23 N22 N21 109.88(18) . . ? N22 N23 N24 109.38(19) . . ? C12 N24 N23 104.73(17) . . ? C13 N25 N26 116.21(18) . . ? C13 N25 H25 117.5(18) . . ? N26 N25 H25 114.9(18) . . ? N25 N26 H26B 107.3(16) . . ? N25 N26 H26C 109.7(18) . . ? H26B N26 H26C 114(3) . . ? N25 N26 H286 110.9(16) . . ? H26B N26 H286 106(2) . . ? H26C N26 H286 110(3) . . ? C13 N27 N28 114.57(18) . . ? C13 N27 H27 111(2) . . ? N28 N27 H27 121(2) . . ? N27 N28 H28A 113.5(17) . . ? N27 N28 H28B 112(2) . . ? H28A N28 H28B 102(2) . . ? N27 N28 H28C 103.8(15) . . ? H28A N28 H28C 116(2) . . ? H28B N28 H28C 110(2) . . ? N1 C1 O2 129.8(2) . . ? N1 C1 C2 111.93(19) . . ? O2 C1 C2 118.29(19) . . ? N2 C2 C1 107.90(19) . . ? N2 C2 C3 124.6(2) . . ? C1 C2 C3 127.38(19) . . ? N3 C3 N6 109.5(2) . . ? N3 C3 C2 125.70(19) . . ? N6 C3 C2 124.83(19) . . ? N7 C4 O2 128.6(2) . . ? N7 C4 C5 111.9(2) . . ? O2 C4 C5 119.52(19) . . ? N8 C5 C4 107.91(19) . . ? N8 C5 C6 124.98(19) . . ? C4 C5 C6 127.1(2) . . ? N9 C6 N12 112.25(19) . . ? N9 C6 C5 124.22(19) . . ? N12 C6 C5 123.53(19) . . ? N13 C7 O5 129.5(2) . . ? N13 C7 C8 111.9(2) . . ? O5 C7 C8 118.57(19) . . ? N14 C8 C7 107.9(2) . . ? N14 C8 C9 124.7(2) . . ? C7 C8 C9 127.36(19) . . ? N15 C9 N18 109.1(2) . . ? N15 C9 C8 126.4(2) . . ? N18 C9 C8 124.49(19) . . ? N19 C10 O5 128.3(2) . . ? N19 C10 C11 112.2(2) . . ? O5 C10 C11 119.5(2) . . ? N20 C11 C10 107.2(2) . . ? N20 C11 C12 126.0(2) . . ? C10 C11 C12 126.7(2) . . ? N21 C12 N24 112.0(2) . . ? N21 C12 C11 125.3(2) . . ? N24 C12 C11 122.61(19) . . ? O7 C13 N25 125.15(19) . . ? O7 C13 N27 123.6(2) . . ? N25 C13 N27 111.24(19) . . ? 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 N2 O1 N1 C1 -0.5(3) . . . . ? N1 O1 N2 C2 0.2(2) . . . . ? C3 N3 N4 N5 0.2(3) . . . . ? N3 N4 N5 N6 -0.2(3) . . . . ? N4 N5 N6 C3 0.2(3) . . . . ? N8 O3 N7 C4 -0.5(2) . . . . ? N7 O3 N8 C5 1.0(2) . . . . ? C6 N9 N10 N11 0.1(3) . . . . ? N9 N10 N11 N12 -0.3(3) . . . . ? N10 N11 N12 C6 0.3(2) . . . . ? N14 O4 N13 C7 -0.4(3) . . . . ? N13 O4 N14 C8 0.0(3) . . . . ? C9 N15 N16 N17 -0.4(3) . . . . ? N15 N16 N17 N18 0.2(3) . . . . ? N16 N17 N18 C9 0.1(3) . . . . ? N20 O6 N19 C10 -0.1(2) . . . . ? N19 O6 N20 C11 0.2(3) . . . . ? C12 N21 N22 N23 -0.1(3) . . . . ? N21 N22 N23 N24 0.3(3) . . . . ? N22 N23 N24 C12 -0.5(2) . . . . ? O1 N1 C1 O2 -178.6(2) . . . . ? O1 N1 C1 C2 0.6(3) . . . . ? C4 O2 C1 N1 -8.2(4) . . . . ? C4 O2 C1 C2 172.7(2) . . . . ? O1 N2 C2 C1 0.2(2) . . . . ? O1 N2 C2 C3 -177.0(2) . . . . ? N1 C1 C2 N2 -0.5(3) . . . . ? O2 C1 C2 N2 178.8(2) . . . . ? N1 C1 C2 C3 176.5(2) . . . . ? O2 C1 C2 C3 -4.2(3) . . . . ? N4 N3 C3 N6 0.0(3) . . . . ? N4 N3 C3 C2 178.8(2) . . . . ? N5 N6 C3 N3 -0.1(3) . . . . ? N5 N6 C3 C2 -178.9(2) . . . . ? N2 C2 C3 N3 -0.1(4) . . . . ? C1 C2 C3 N3 -176.7(2) . . . . ? N2 C2 C3 N6 178.6(2) . . . . ? C1 C2 C3 N6 2.0(4) . . . . ? O3 N7 C4 O2 179.1(2) . . . . ? O3 N7 C4 C5 -0.2(2) . . . . ? C1 O2 C4 N7 7.7(4) . . . . ? C1 O2 C4 C5 -173.0(2) . . . . ? O3 N8 C5 C4 -1.1(2) . . . . ? O3 N8 C5 C6 176.9(2) . . . . ? N7 C4 C5 N8 0.9(3) . . . . ? O2 C4 C5 N8 -178.5(2) . . . . ? N7 C4 C5 C6 -177.0(2) . . . . ? O2 C4 C5 C6 3.5(3) . . . . ? N10 N9 C6 N12 0.2(3) . . . . ? N10 N9 C6 C5 -179.7(2) . . . . ? N11 N12 C6 N9 -0.3(2) . . . . ? N11 N12 C6 C5 179.6(2) . . . . ? N8 C5 C6 N9 3.9(4) . . . . ? C4 C5 C6 N9 -178.5(2) . . . . ? N8 C5 C6 N12 -175.9(2) . . . . ? C4 C5 C6 N12 1.7(3) . . . . ? O4 N13 C7 O5 -178.5(2) . . . . ? O4 N13 C7 C8 0.6(3) . . . . ? C10 O5 C7 N13 -2.7(4) . . . . ? C10 O5 C7 C8 178.2(2) . . . . ? O4 N14 C8 C7 0.4(2) . . . . ? O4 N14 C8 C9 -178.1(2) . . . . ? N13 C7 C8 N14 -0.7(3) . . . . ? O5 C7 C8 N14 178.5(2) . . . . ? N13 C7 C8 C9 177.7(2) . . . . ? O5 C7 C8 C9 -3.1(4) . . . . ? N16 N15 C9 N18 0.4(2) . . . . ? N16 N15 C9 C8 -178.0(2) . . . . ? N17 N18 C9 N15 -0.3(3) . . . . ? N17 N18 C9 C8 178.1(2) . . . . ? N14 C8 C9 N15 2.8(4) . . . . ? C7 C8 C9 N15 -175.4(2) . . . . ? N14 C8 C9 N18 -175.4(2) . . . . ? C7 C8 C9 N18 6.4(4) . . . . ? O6 N19 C10 O5 179.7(2) . . . . ? O6 N19 C10 C11 -0.1(3) . . . . ? C7 O5 C10 N19 0.5(4) . . . . ? C7 O5 C10 C11 -179.7(2) . . . . ? O6 N20 C11 C10 -0.2(2) . . . . ? O6 N20 C11 C12 178.0(2) . . . . ? N19 C10 C11 N20 0.2(3) . . . . ? O5 C10 C11 N20 -179.6(2) . . . . ? N19 C10 C11 C12 -178.0(2) . . . . ? O5 C10 C11 C12 2.2(3) . . . . ? N22 N21 C12 N24 -0.2(3) . . . . ? N22 N21 C12 C11 -179.9(2) . . . . ? N23 N24 C12 N21 0.4(3) . . . . ? N23 N24 C12 C11 -179.9(2) . . . . ? N20 C11 C12 N21 0.9(4) . . . . ? C10 C11 C12 N21 178.8(2) . . . . ? N20 C11 C12 N24 -178.7(2) . . . . ? C10 C11 C12 N24 -0.8(3) . . . . ? N26 N25 C13 O7 10.5(3) . . . . ? N26 N25 C13 N27 -169.87(18) . . . . ? N28 N27 C13 O7 10.5(3) . . . . ? N28 N27 C13 N25 -169.18(19) . . . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 30.07 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.225 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.052 data_bo1642 _database_code_depnum_ccdc_archive 'CCDC 885845' #TrackingRef 'Bo1642' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H14 N20 O3' _chemical_formula_weight 438.39 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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 10.223(4) _cell_length_b 12.234(4) _cell_length_c 14.849(5) _cell_angle_alpha 90.00 _cell_angle_beta 107.163(4) _cell_angle_gamma 90.00 _cell_volume 1774.5(10) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 2893 _cell_measurement_theta_min 2.668 _cell_measurement_theta_max 30.024 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.641 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.133 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC10/Saturn724+ _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5947 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_sigmaI/netI 0.0524 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 30.02 _reflns_number_total 2535 _reflns_number_gt 1807 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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 full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0385P)^2^+0.1060P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment X,Y,Z,Ueq _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2535 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0642 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.0997 _refine_ls_wR_factor_gt 0.0907 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.66550(11) 0.37791(8) 0.42754(7) 0.0283(3) Uani 1 1 d . . . O2 O 0.5000 0.55460(11) 0.2500 0.0229(3) Uani 1 2 d S . . N1 N 0.59833(12) 0.39652(10) 0.33360(8) 0.0252(3) Uani 1 1 d . . . N2 N 0.66710(12) 0.47115(9) 0.48009(8) 0.0253(3) Uani 1 1 d . . . N3 N 0.63619(12) 0.68768(9) 0.54327(8) 0.0237(3) Uani 1 1 d . . . N4 N 0.59065(13) 0.79023(10) 0.54455(8) 0.0264(3) Uani 1 1 d . . . N5 N 0.51226(13) 0.81681(10) 0.45967(8) 0.0259(3) Uani 1 1 d . . . N6 N 0.50490(12) 0.73247(9) 0.40016(8) 0.0229(3) Uani 1 1 d . . . N7 N 0.90534(12) 0.49236(11) 0.84007(8) 0.0230(3) Uani 1 1 d . . . N8 N 0.83891(13) 0.63068(10) 0.73035(10) 0.0241(3) Uani 1 1 d . . . N9 N 0.78011(13) 0.45468(10) 0.68713(9) 0.0270(3) Uani 1 1 d . . . N10 N 0.8017(2) 0.34314(12) 0.70819(10) 0.0429(4) Uani 1 1 d . . . C1 C 0.56227(13) 0.49851(11) 0.33016(9) 0.0196(3) Uani 1 1 d . . . C2 C 0.60321(13) 0.54653(11) 0.42143(9) 0.0189(3) Uani 1 1 d . . . C3 C 0.58246(13) 0.65535(11) 0.45407(9) 0.0191(3) Uani 1 1 d . . . C4 C 0.84273(13) 0.52601(11) 0.75360(9) 0.0198(3) Uani 1 1 d . . . H7A H 0.9384(17) 0.5430(14) 0.8854(12) 0.035(5) Uiso 1 1 d . . . H7B H 0.9016(16) 0.4231(16) 0.8541(11) 0.040(5) Uiso 1 1 d . . . H8A H 0.7853(17) 0.6488(14) 0.6751(12) 0.036(5) Uiso 1 1 d . . . H8B H 0.8814(18) 0.6776(15) 0.7734(13) 0.044(5) Uiso 1 1 d . . . H9 H 0.7546(18) 0.4730(15) 0.6280(15) 0.048(6) Uiso 1 1 d . . . H10A H 0.725(2) 0.3102(17) 0.6805(14) 0.058(6) Uiso 1 1 d . . . H10B H 0.875(2) 0.3140(19) 0.6890(15) 0.076(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0413(6) 0.0188(5) 0.0213(5) -0.0005(4) 0.0035(4) 0.0091(4) O2 0.0346(7) 0.0184(7) 0.0133(7) 0.000 0.0034(6) 0.000 N1 0.0331(6) 0.0230(6) 0.0184(6) 0.0003(5) 0.0059(5) 0.0054(5) N2 0.0360(7) 0.0180(6) 0.0198(6) -0.0016(5) 0.0048(5) 0.0036(5) N3 0.0319(6) 0.0181(6) 0.0176(6) -0.0003(5) 0.0018(5) 0.0026(5) N4 0.0370(7) 0.0183(6) 0.0193(6) -0.0003(5) 0.0011(5) 0.0033(5) N5 0.0358(7) 0.0178(6) 0.0196(6) -0.0016(5) 0.0010(5) 0.0024(5) N6 0.0310(6) 0.0163(6) 0.0180(6) -0.0011(5) 0.0018(5) 0.0009(5) N7 0.0301(6) 0.0165(6) 0.0175(6) 0.0021(5) -0.0007(5) -0.0031(5) N8 0.0305(6) 0.0188(6) 0.0196(7) 0.0035(5) 0.0021(5) -0.0008(5) N9 0.0352(7) 0.0228(7) 0.0182(6) 0.0012(5) 0.0002(5) -0.0065(5) N10 0.0610(11) 0.0202(7) 0.0348(8) -0.0008(6) -0.0057(8) -0.0095(7) C1 0.0231(6) 0.0196(7) 0.0169(7) 0.0007(5) 0.0070(5) 0.0009(5) C2 0.0226(6) 0.0182(7) 0.0154(6) 0.0014(5) 0.0046(5) 0.0002(5) C3 0.0233(6) 0.0172(6) 0.0153(6) 0.0022(5) 0.0035(5) -0.0008(5) C4 0.0192(6) 0.0215(7) 0.0176(7) 0.0013(5) 0.0035(5) -0.0013(5) _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 N2 1.3795(15) . ? O1 N1 1.3799(15) . ? O2 C1 1.3585(15) 2_655 ? O2 C1 1.3586(15) . ? N1 C1 1.2978(17) . ? N2 C2 1.3038(17) . ? N3 C3 1.3353(17) . ? N3 N4 1.3403(16) . ? N4 N5 1.3192(16) . ? N5 N6 1.3462(16) . ? N6 C3 1.3361(17) . ? N7 C4 1.3201(18) . ? N7 H7A 0.904(17) . ? N7 H7B 0.876(19) . ? N8 C4 1.3239(17) . ? N8 H8A 0.871(17) . ? N8 H8B 0.873(19) . ? N9 C4 1.3314(18) . ? N9 N10 1.4028(18) . ? N9 H9 0.87(2) . ? N10 H10A 0.87(2) . ? N10 H10B 0.95(2) . ? C1 C2 1.4222(19) . ? C2 C3 1.4537(18) . ? 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 N2 O1 N1 110.78(10) . . ? C1 O2 C1 119.32(15) 2_655 . ? C1 N1 O1 104.43(10) . . ? C2 N2 O1 106.68(11) . . ? C3 N3 N4 104.39(11) . . ? N5 N4 N3 109.44(11) . . ? N4 N5 N6 109.80(11) . . ? C3 N6 N5 103.86(11) . . ? C4 N7 H7A 118.6(11) . . ? C4 N7 H7B 119.4(10) . . ? H7A N7 H7B 121.2(15) . . ? C4 N8 H8A 117.0(11) . . ? C4 N8 H8B 118.4(12) . . ? H8A N8 H8B 124.1(16) . . ? C4 N9 N10 117.56(12) . . ? C4 N9 H9 121.0(12) . . ? N10 N9 H9 117.2(12) . . ? N9 N10 H10A 106.4(14) . . ? N9 N10 H10B 112.6(14) . . ? H10A N10 H10B 111.8(19) . . ? N1 C1 O2 125.05(12) . . ? N1 C1 C2 111.06(12) . . ? O2 C1 C2 123.80(12) . . ? N2 C2 C1 107.04(12) . . ? N2 C2 C3 121.24(12) . . ? C1 C2 C3 131.70(12) . . ? N3 C3 N6 112.51(12) . . ? N3 C3 C2 122.98(12) . . ? N6 C3 C2 124.48(12) . . ? N7 C4 N8 121.58(13) . . ? N7 C4 N9 120.38(13) . . ? N8 C4 N9 118.04(13) . . ? 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 N2 O1 N1 C1 0.69(14) . . . . ? N1 O1 N2 C2 -0.08(15) . . . . ? C3 N3 N4 N5 0.53(15) . . . . ? N3 N4 N5 N6 -0.36(16) . . . . ? N4 N5 N6 C3 0.03(15) . . . . ? O1 N1 C1 O2 175.79(11) . . . . ? O1 N1 C1 C2 -1.01(14) . . . . ? C1 O2 C1 N1 18.16(10) 2_655 . . . ? C1 O2 C1 C2 -165.44(14) 2_655 . . . ? O1 N2 C2 C1 -0.52(15) . . . . ? O1 N2 C2 C3 178.15(11) . . . . ? N1 C1 C2 N2 1.01(16) . . . . ? O2 C1 C2 N2 -175.83(11) . . . . ? N1 C1 C2 C3 -177.47(13) . . . . ? O2 C1 C2 C3 5.7(2) . . . . ? N4 N3 C3 N6 -0.53(15) . . . . ? N4 N3 C3 C2 -178.43(12) . . . . ? N5 N6 C3 N3 0.32(15) . . . . ? N5 N6 C3 C2 178.18(12) . . . . ? N2 C2 C3 N3 5.7(2) . . . . ? C1 C2 C3 N3 -176.02(14) . . . . ? N2 C2 C3 N6 -171.96(13) . . . . ? C1 C2 C3 N6 6.3(2) . . . . ? N10 N9 C4 N7 -9.9(2) . . . . ? N10 N9 C4 N8 170.69(15) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.211 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.052 data_bo1636 _database_code_depnum_ccdc_archive 'CCDC 886131' #TrackingRef 'Bo1636.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H12 N18 O3' _chemical_formula_weight 408.36 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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 10.489(6) _cell_length_b 11.018(6) _cell_length_c 15.197(8) _cell_angle_alpha 90.00 _cell_angle_beta 109.451(7) _cell_angle_gamma 90.00 _cell_volume 1656.0(15) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 3082 _cell_measurement_theta_min 2.768 _cell_measurement_theta_max 30.032 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.638 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.133 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC10/Saturn724+ _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5732 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0641 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 30.05 _reflns_number_total 2423 _reflns_number_gt 1563 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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 full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0269P)^2^+0.1390P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment X,Y,Z,Ueq _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2423 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0682 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.0986 _refine_ls_wR_factor_gt 0.0914 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.68110(12) 0.32009(10) 0.42382(8) 0.0385(3) Uani 1 1 d . . . O2 O 0.5000 0.51391(12) 0.2500 0.0284(3) Uani 1 2 d S . . N1 N 0.60976(13) 0.34060(11) 0.33096(9) 0.0313(3) Uani 1 1 d . . . N2 N 0.68330(13) 0.42227(11) 0.47714(9) 0.0322(3) Uani 1 1 d . . . N3 N 0.64154(12) 0.65536(11) 0.54122(8) 0.0275(3) Uani 1 1 d . . . N4 N 0.59811(13) 0.76992(11) 0.54282(9) 0.0314(3) Uani 1 1 d . . . N5 N 0.52714(13) 0.80413(11) 0.45752(9) 0.0312(3) Uani 1 1 d . . . N6 N 0.52110(12) 0.71306(10) 0.39715(8) 0.0261(3) Uani 1 1 d . . . N7 N 0.83976(13) 0.62651(13) 0.73138(10) 0.0300(3) Uani 1 1 d . . . N8 N 0.78455(14) 0.42558(15) 0.69989(10) 0.0371(4) Uani 1 1 d . . . N9 N 0.91162(13) 0.48438(13) 0.84767(9) 0.0327(3) Uani 1 1 d . . . C1 C 0.56973(13) 0.45232(13) 0.32865(10) 0.0229(3) Uani 1 1 d . . . C2 C 0.61416(13) 0.50451(12) 0.41879(10) 0.0224(3) Uani 1 1 d . . . C3 C 0.59226(13) 0.62438(12) 0.45107(9) 0.0213(3) Uani 1 1 d . . . C4 C 0.84694(13) 0.51248(13) 0.76020(10) 0.0249(3) Uani 1 1 d . . . H7A H 0.7936(16) 0.6428(15) 0.6697(13) 0.039(5) Uiso 1 1 d . . . H7B H 0.8828(16) 0.6847(15) 0.7701(13) 0.040(5) Uiso 1 1 d . . . H8A H 0.7502(17) 0.4417(16) 0.6376(15) 0.055(6) Uiso 1 1 d . . . H8B H 0.807(2) 0.345(2) 0.7186(17) 0.102(9) Uiso 1 1 d . . . H9A H 0.9520(16) 0.5435(16) 0.8885(13) 0.042(5) Uiso 1 1 d . . . H9B H 0.9088(16) 0.4082(17) 0.8690(13) 0.059(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0558(7) 0.0277(6) 0.0234(6) 0.0006(5) 0.0017(5) 0.0126(5) O2 0.0450(8) 0.0229(8) 0.0116(7) 0.000 0.0017(6) 0.000 N1 0.0455(8) 0.0273(7) 0.0182(7) 0.0010(5) 0.0065(6) 0.0078(5) N2 0.0453(8) 0.0255(7) 0.0205(7) -0.0007(5) 0.0039(6) 0.0065(5) N3 0.0345(7) 0.0286(7) 0.0148(6) -0.0018(5) 0.0021(5) 0.0033(5) N4 0.0415(7) 0.0283(7) 0.0195(7) -0.0040(6) 0.0035(6) 0.0031(5) N5 0.0420(7) 0.0276(7) 0.0177(6) -0.0028(5) 0.0014(6) 0.0042(5) N6 0.0359(7) 0.0219(6) 0.0163(6) 0.0002(5) 0.0030(5) 0.0007(5) N7 0.0336(7) 0.0333(8) 0.0177(7) 0.0072(6) 0.0014(6) 0.0004(6) N8 0.0455(8) 0.0413(9) 0.0180(7) -0.0041(6) 0.0021(6) -0.0112(6) N9 0.0472(8) 0.0262(8) 0.0167(7) 0.0030(6) -0.0002(6) -0.0079(6) C1 0.0303(7) 0.0230(7) 0.0151(7) 0.0028(6) 0.0071(6) 0.0011(6) C2 0.0265(7) 0.0241(7) 0.0149(7) 0.0022(6) 0.0045(5) 0.0006(5) C3 0.0248(7) 0.0231(7) 0.0137(6) 0.0006(6) 0.0033(5) -0.0005(5) C4 0.0253(7) 0.0305(8) 0.0180(7) 0.0005(6) 0.0060(6) -0.0036(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.3782(17) . ? O1 N2 1.3829(17) . ? O2 C1 1.3571(15) . ? O2 C1 1.3571(15) 2_655 ? N1 C1 1.2973(19) . ? N2 C2 1.3058(18) . ? N3 C3 1.3376(18) . ? N3 N4 1.3449(18) . ? N4 N5 1.3167(18) . ? N5 N6 1.3467(17) . ? N6 C3 1.3326(17) . ? N7 C4 1.324(2) . ? N7 H7A 0.918(17) . ? N7 H7B 0.886(17) . ? N8 C4 1.336(2) . ? N8 H8A 0.91(2) . ? N8 H8B 0.94(3) . ? N9 C4 1.312(2) . ? N9 H9A 0.902(17) . ? N9 H9B 0.904(18) . ? C1 C2 1.414(2) . ? C2 C3 1.453(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 N1 O1 N2 111.34(11) . . ? C1 O2 C1 120.00(16) . 2_655 ? C1 N1 O1 104.11(12) . . ? C2 N2 O1 105.66(12) . . ? C3 N3 N4 103.90(11) . . ? N5 N4 N3 109.56(12) . . ? N4 N5 N6 109.90(12) . . ? C3 N6 N5 103.75(12) . . ? C4 N7 H7A 118.4(10) . . ? C4 N7 H7B 120.4(11) . . ? H7A N7 H7B 121.0(15) . . ? C4 N8 H8A 120.4(11) . . ? C4 N8 H8B 116.9(15) . . ? H8A N8 H8B 118.2(18) . . ? C4 N9 H9A 119.5(11) . . ? C4 N9 H9B 120.9(12) . . ? H9A N9 H9B 119.3(16) . . ? N1 C1 O2 124.95(13) . . ? N1 C1 C2 111.13(12) . . ? O2 C1 C2 123.85(13) . . ? N2 C2 C1 107.76(13) . . ? N2 C2 C3 121.05(13) . . ? C1 C2 C3 131.17(12) . . ? N6 C3 N3 112.89(12) . . ? N6 C3 C2 125.30(13) . . ? N3 C3 C2 121.80(12) . . ? N9 C4 N7 120.80(14) . . ? N9 C4 N8 119.70(15) . . ? N7 C4 N8 119.47(15) . . ? 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 N2 O1 N1 C1 -0.20(16) . . . . ? N1 O1 N2 C2 0.33(16) . . . . ? C3 N3 N4 N5 -0.15(16) . . . . ? N3 N4 N5 N6 0.26(17) . . . . ? N4 N5 N6 C3 -0.26(16) . . . . ? O1 N1 C1 O2 177.00(12) . . . . ? O1 N1 C1 C2 0.00(16) . . . . ? C1 O2 C1 N1 21.06(11) 2_655 . . . ? C1 O2 C1 C2 -162.30(16) 2_655 . . . ? O1 N2 C2 C1 -0.32(15) . . . . ? O1 N2 C2 C3 178.51(12) . . . . ? N1 C1 C2 N2 0.21(17) . . . . ? O2 C1 C2 N2 -176.83(12) . . . . ? N1 C1 C2 C3 -178.45(14) . . . . ? O2 C1 C2 C3 4.5(2) . . . . ? N5 N6 C3 N3 0.17(16) . . . . ? N5 N6 C3 C2 178.87(13) . . . . ? N4 N3 C3 N6 -0.02(16) . . . . ? N4 N3 C3 C2 -178.77(13) . . . . ? N2 C2 C3 N6 -178.62(14) . . . . ? C1 C2 C3 N6 -0.1(2) . . . . ? N2 C2 C3 N3 0.0(2) . . . . ? C1 C2 C3 N3 178.48(14) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 30.05 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.203 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.062