# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Di Sun' _publ_contact_author_email dsun@sdu.edu.cn _publ_section_title ; Conformation variation of tris(2-carboxyethyl)isocyanuric acid induced by cocrystallized N-heterocyclic organic molecules ; loop_ _publ_author_name 'Fangna Dai' 'Di Sun' 'Daofeng Sun' data_p3 #TrackingRef '- p1-3-r1.cif' _database_code_depnum_ccdc_archive 'CCDC 796379' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H27 N6 O9' _chemical_formula_weight 579.55 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 0.0016 '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 8.375(4) _cell_length_b 11.257(5) _cell_length_c 15.807(6) _cell_angle_alpha 69.947(7) _cell_angle_beta 75.476(7) _cell_angle_gamma 84.278(7) _cell_volume 1354.9(10) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1969 _cell_measurement_theta_min 5.025 _cell_measurement_theta_max 49.141 _exptl_crystal_description block _exptl_crystal_colour plate _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 606 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9892 _exptl_absorpt_correction_T_max 0.9946 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6641 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0561 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4688 _reflns_number_gt 3262 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.1362P)^2^+0.0384P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4688 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0886 _refine_ls_R_factor_gt 0.0637 _refine_ls_wR_factor_ref 0.2101 _refine_ls_wR_factor_gt 0.1807 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5154(3) 0.4132(3) 0.3015(2) 0.0466(7) Uani 1 1 d . . . C2 C 0.2586(3) 0.2976(3) 0.3472(2) 0.0491(7) Uani 1 1 d . . . C3 C 0.5196(3) 0.1815(2) 0.36079(19) 0.0442(6) Uani 1 1 d . . . C4 C 0.7770(3) 0.2975(3) 0.3153(2) 0.0477(7) Uani 1 1 d . . . H4A H 0.8066 0.2305 0.3671 0.057 Uiso 1 1 calc R . . H4B H 0.8077 0.3772 0.3172 0.057 Uiso 1 1 calc R . . C5 C 0.8739(3) 0.2787(3) 0.2258(2) 0.0514(7) Uani 1 1 d . . . H5A H 0.9908 0.2761 0.2239 0.062 Uiso 1 1 calc R . . H5B H 0.8452 0.1982 0.2243 0.062 Uiso 1 1 calc R . . C6 C 0.8397(3) 0.3822(3) 0.1429(2) 0.0515(7) Uani 1 1 d . . . C7 C 0.2527(3) 0.5284(3) 0.2900(2) 0.0544(7) Uani 1 1 d . . . H7A H 0.3056 0.5912 0.3028 0.065 Uiso 1 1 calc R . . H7B H 0.1423 0.5162 0.3295 0.065 Uiso 1 1 calc R . . C8 C 0.2409(4) 0.5776(3) 0.1905(2) 0.0583(8) Uani 1 1 d . . . H8A H 0.3494 0.6035 0.1513 0.070 Uiso 1 1 calc R . . H8B H 0.2055 0.5100 0.1748 0.070 Uiso 1 1 calc R . . C9 C 0.1227(4) 0.6876(3) 0.1710(2) 0.0555(8) Uani 1 1 d . . . C10 C 0.2585(3) 0.0670(3) 0.4099(2) 0.0522(7) Uani 1 1 d . . . H10A H 0.1470 0.0811 0.4419 0.063 Uiso 1 1 calc R . . H10B H 0.3121 0.0053 0.4544 0.063 Uiso 1 1 calc R . . C11 C 0.2523(4) 0.0168(3) 0.3352(2) 0.0620(8) Uani 1 1 d . . . H11A H 0.3622 -0.0102 0.3101 0.074 Uiso 1 1 calc R . . H11B H 0.2163 0.0837 0.2856 0.074 Uiso 1 1 calc R . . C12 C 0.1366(4) -0.0933(3) 0.3700(2) 0.0581(8) Uani 1 1 d . . . C13 C 0.6777(4) 0.6552(3) 0.9753(3) 0.0698(10) Uani 1 1 d . . . H13A H 0.6579 0.5707 0.9864 0.084 Uiso 1 1 calc R . . C14 C 0.5696(4) 0.7446(3) 0.9369(2) 0.0647(9) Uani 1 1 d . . . H14A H 0.4793 0.7199 0.9230 0.078 Uiso 1 1 calc R . . C15 C 0.5941(3) 0.8710(2) 0.91877(18) 0.0431(6) Uani 1 1 d . . . C16 C 0.7350(3) 0.8999(3) 0.9382(2) 0.0534(7) Uani 1 1 d . . . H16A H 0.7609 0.9838 0.9249 0.064 Uiso 1 1 calc R . . C17 C 0.8366(4) 0.8036(3) 0.9773(2) 0.0558(8) Uani 1 1 d . . . H17A H 0.9300 0.8254 0.9902 0.067 Uiso 1 1 calc R . . C18 C 0.2134(4) 1.0319(3) 0.8439(3) 0.0689(9) Uani 1 1 d . . . H18A H 0.1106 1.0082 0.8432 0.083 Uiso 1 1 calc R . . C19 C 0.3214(4) 0.9382(3) 0.8784(2) 0.0611(8) Uani 1 1 d . . . H19A H 0.2912 0.8538 0.8998 0.073 Uiso 1 1 calc R . . C20 C 0.4748(3) 0.9697(2) 0.88124(18) 0.0439(6) Uani 1 1 d . . . C21 C 0.5102(4) 1.0969(3) 0.8474(2) 0.0591(8) Uani 1 1 d . . . H21A H 0.6119 1.1235 0.8474 0.071 Uiso 1 1 calc R . . C22 C 0.3947(4) 1.1846(3) 0.8138(2) 0.0635(8) Uani 1 1 d . . . H22A H 0.4215 1.2697 0.7914 0.076 Uiso 1 1 calc R . . C23 C 0.6271(4) 0.7713(3) 0.4269(2) 0.0623(8) Uani 1 1 d . . . H23A H 0.5908 0.8551 0.4088 0.075 Uiso 1 1 calc R . . C24 C 0.5126(4) 0.6770(3) 0.4564(2) 0.0586(8) Uani 1 1 d . . . H24A H 0.4019 0.6983 0.4580 0.070 Uiso 1 1 calc R . . C25 C 0.5603(3) 0.5526(2) 0.48350(18) 0.0434(6) Uani 1 1 d . . . C26 C 0.7282(3) 0.5272(3) 0.4780(2) 0.0528(7) Uani 1 1 d . . . H26A H 0.7683 0.4443 0.4942 0.063 Uiso 1 1 calc R . . C27 C 0.8344(3) 0.6281(3) 0.4477(2) 0.0575(8) Uani 1 1 d . . . H27A H 0.9462 0.6104 0.4446 0.069 Uiso 1 1 calc R . . N1 N 0.5964(2) 0.29751(19) 0.32604(16) 0.0449(5) Uani 1 1 d . . . N2 N 0.3462(3) 0.4082(2) 0.31300(16) 0.0479(6) Uani 1 1 d . . . N3 N 0.3498(3) 0.1872(2) 0.37154(16) 0.0471(6) Uani 1 1 d . . . N4 N 0.8091(3) 0.6820(2) 0.99766(18) 0.0571(7) Uani 1 1 d . . . N5 N 0.2478(3) 1.1542(2) 0.81159(18) 0.0609(7) Uani 1 1 d . . . N6 N 0.7860(3) 0.7481(2) 0.42315(18) 0.0570(6) Uani 1 1 d . . . O1 O 0.5861(3) 0.51166(18) 0.27316(17) 0.0663(6) Uani 1 1 d . . . O2 O 0.1112(2) 0.2976(2) 0.35574(17) 0.0714(7) Uani 1 1 d . . . O3 O 0.5945(2) 0.08341(18) 0.38092(16) 0.0626(6) Uani 1 1 d . . . O4 O 0.7336(3) 0.3758(2) 0.1060(2) 0.0878(9) Uani 1 1 d . . . O5 O 0.9329(2) 0.48168(18) 0.11675(14) 0.0557(5) Uani 1 1 d . . . H5C H 0.9089 0.5353 0.0713 0.083 Uiso 1 1 calc R . . O6 O 0.1515(3) 0.7818(2) 0.1049(2) 0.0914(8) Uani 1 1 d . . . O7 O -0.0183(3) 0.6683(2) 0.23318(16) 0.0741(7) Uani 1 1 d . . . H7C H -0.0790 0.7304 0.2200 0.111 Uiso 1 1 calc R . . O8 O -0.0070(3) -0.0628(2) 0.3568(2) 0.1033(10) Uani 1 1 d . . . H8C H -0.0638 -0.1262 0.3772 0.155 Uiso 1 1 calc R . . O9 O 0.1709(4) -0.1979(3) 0.4070(4) 0.168(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0420(15) 0.0375(15) 0.0624(18) -0.0146(13) -0.0203(13) 0.0039(12) C2 0.0387(16) 0.0527(17) 0.0583(17) -0.0163(14) -0.0192(12) 0.0012(12) C3 0.0381(14) 0.0376(15) 0.0552(16) -0.0081(12) -0.0177(12) -0.0016(11) C4 0.0345(14) 0.0432(15) 0.0666(18) -0.0120(13) -0.0225(13) -0.0007(11) C5 0.0383(15) 0.0454(16) 0.0699(19) -0.0140(14) -0.0204(13) 0.0046(11) C6 0.0443(16) 0.0490(17) 0.0644(19) -0.0188(14) -0.0181(14) 0.0001(12) C7 0.0464(16) 0.0494(16) 0.070(2) -0.0197(15) -0.0242(14) 0.0165(13) C8 0.0479(17) 0.0605(19) 0.0659(19) -0.0184(15) -0.0200(14) 0.0099(14) C9 0.0482(18) 0.0514(18) 0.066(2) -0.0087(16) -0.0280(15) 0.0040(13) C10 0.0426(16) 0.0503(17) 0.0568(17) -0.0059(14) -0.0120(13) -0.0109(12) C11 0.0513(18) 0.069(2) 0.0632(19) -0.0167(16) -0.0066(14) -0.0231(15) C12 0.0456(17) 0.0456(18) 0.081(2) -0.0124(16) -0.0212(15) -0.0059(13) C13 0.073(2) 0.0446(17) 0.103(3) -0.0211(17) -0.049(2) 0.0078(15) C14 0.065(2) 0.0419(17) 0.098(3) -0.0186(16) -0.0466(18) 0.0054(14) C15 0.0424(15) 0.0447(15) 0.0438(15) -0.0146(12) -0.0146(11) 0.0048(11) C16 0.0510(17) 0.0482(17) 0.0610(18) -0.0146(14) -0.0172(14) -0.0028(13) C17 0.0472(17) 0.0562(19) 0.0649(19) -0.0150(15) -0.0222(14) 0.0007(13) C18 0.0535(19) 0.055(2) 0.098(3) -0.0131(18) -0.0370(18) 0.0048(14) C19 0.0542(18) 0.0406(16) 0.086(2) -0.0100(15) -0.0284(16) 0.0000(13) C20 0.0449(15) 0.0432(15) 0.0441(15) -0.0142(12) -0.0130(12) 0.0033(11) C21 0.0534(18) 0.0373(16) 0.085(2) -0.0137(15) -0.0229(15) 0.0017(13) C22 0.061(2) 0.0409(17) 0.079(2) -0.0074(15) -0.0183(16) 0.0014(14) C23 0.0564(19) 0.0434(17) 0.086(2) -0.0128(16) -0.0258(16) -0.0048(14) C24 0.0420(16) 0.0475(17) 0.086(2) -0.0133(16) -0.0255(15) -0.0021(12) C25 0.0420(15) 0.0413(15) 0.0496(16) -0.0127(12) -0.0165(12) -0.0064(11) C26 0.0397(15) 0.0456(16) 0.074(2) -0.0178(14) -0.0183(13) -0.0009(12) C27 0.0364(15) 0.0578(19) 0.074(2) -0.0159(16) -0.0112(14) -0.0093(13) N1 0.0333(12) 0.0365(12) 0.0651(15) -0.0119(10) -0.0188(10) -0.0002(9) N2 0.0369(12) 0.0432(13) 0.0644(15) -0.0141(11) -0.0209(10) 0.0057(10) N3 0.0347(12) 0.0429(13) 0.0627(15) -0.0104(11) -0.0184(10) -0.0032(9) N4 0.0527(15) 0.0530(15) 0.0681(16) -0.0186(13) -0.0253(12) 0.0116(11) N5 0.0586(17) 0.0505(15) 0.0692(17) -0.0114(13) -0.0238(13) 0.0124(12) N6 0.0500(15) 0.0516(15) 0.0679(16) -0.0122(12) -0.0164(12) -0.0141(11) O1 0.0517(12) 0.0357(11) 0.1107(18) -0.0165(11) -0.0283(12) -0.0003(9) O2 0.0307(11) 0.0799(15) 0.1033(18) -0.0224(13) -0.0257(11) -0.0009(10) O3 0.0479(12) 0.0366(11) 0.0938(16) -0.0042(10) -0.0263(11) 0.0052(9) O4 0.0957(19) 0.0613(15) 0.120(2) -0.0082(13) -0.0753(17) -0.0134(13) O5 0.0467(12) 0.0497(12) 0.0682(13) -0.0077(10) -0.0246(10) -0.0033(9) O6 0.0673(16) 0.0695(16) 0.104(2) 0.0159(15) -0.0246(14) 0.0048(12) O7 0.0625(15) 0.0606(14) 0.0813(16) -0.0058(12) -0.0198(12) 0.0241(11) O8 0.0561(16) 0.0605(15) 0.175(3) 0.0011(16) -0.0437(17) -0.0194(12) O9 0.077(2) 0.071(2) 0.311(5) 0.038(3) -0.101(3) -0.0225(15) _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 C1 O1 1.199(3) . ? C1 N1 1.384(3) . ? C1 N2 1.387(3) . ? C2 O2 1.207(3) . ? C2 N2 1.379(3) . ? C2 N3 1.380(3) . ? C3 O3 1.198(3) . ? C3 N1 1.385(3) . ? C3 N3 1.387(3) . ? C4 N1 1.479(3) . ? C4 C5 1.516(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.494(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O4 1.198(3) . ? C6 O5 1.315(3) . ? C7 N2 1.474(3) . ? C7 C8 1.504(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.502(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 O6 1.199(4) . ? C9 O7 1.316(4) . ? C10 N3 1.481(3) . ? C10 C11 1.487(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.511(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 O9 1.165(4) . ? C12 O8 1.265(4) . ? C13 N4 1.327(4) . ? C13 C14 1.370(4) . ? C13 H13A 0.9300 . ? C14 C15 1.377(4) . ? C14 H14A 0.9300 . ? C15 C16 1.385(4) . ? C15 C20 1.486(4) . ? C16 C17 1.379(4) . ? C16 H16A 0.9300 . ? C17 N4 1.325(4) . ? C17 H17A 0.9300 . ? C18 N5 1.327(4) . ? C18 C19 1.375(4) . ? C18 H18A 0.9300 . ? C19 C20 1.382(4) . ? C19 H19A 0.9300 . ? C20 C21 1.380(4) . ? C21 C22 1.379(4) . ? C21 H21A 0.9300 . ? C22 N5 1.321(4) . ? C22 H22A 0.9300 . ? C23 N6 1.321(4) . ? C23 C24 1.380(4) . ? C23 H23A 0.9300 . ? C24 C25 1.367(4) . ? C24 H24A 0.9300 . ? C25 C26 1.394(4) . ? C25 C25 1.498(5) 2_666 ? C26 C27 1.388(4) . ? C26 H26A 0.9300 . ? C27 N6 1.322(4) . ? C27 H27A 0.9300 . ? O5 H5C 0.8200 . ? O7 H7C 0.8200 . ? O8 H8C 0.8200 . ? 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 O1 C1 N1 122.4(2) . . ? O1 C1 N2 121.9(2) . . ? N1 C1 N2 115.7(2) . . ? O2 C2 N2 122.0(3) . . ? O2 C2 N3 122.2(3) . . ? N2 C2 N3 115.8(2) . . ? O3 C3 N1 122.3(2) . . ? O3 C3 N3 122.5(2) . . ? N1 C3 N3 115.2(2) . . ? N1 C4 C5 113.0(2) . . ? N1 C4 H4A 109.0 . . ? C5 C4 H4A 109.0 . . ? N1 C4 H4B 109.0 . . ? C5 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? C6 C5 C4 111.8(2) . . ? C6 C5 H5A 109.2 . . ? C4 C5 H5A 109.2 . . ? C6 C5 H5B 109.2 . . ? C4 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? O4 C6 O5 123.7(3) . . ? O4 C6 C5 122.7(3) . . ? O5 C6 C5 113.6(2) . . ? N2 C7 C8 112.9(2) . . ? N2 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? N2 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C9 C8 C7 112.8(2) . . ? C9 C8 H8A 109.0 . . ? C7 C8 H8A 109.0 . . ? C9 C8 H8B 109.0 . . ? C7 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? O6 C9 O7 123.4(3) . . ? O6 C9 C8 124.0(3) . . ? O7 C9 C8 112.6(3) . . ? N3 C10 C11 110.9(2) . . ? N3 C10 H10A 109.5 . . ? C11 C10 H10A 109.5 . . ? N3 C10 H10B 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 108.0 . . ? C10 C11 C12 111.9(2) . . ? C10 C11 H11A 109.2 . . ? C12 C11 H11A 109.2 . . ? C10 C11 H11B 109.2 . . ? C12 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? O9 C12 O8 121.0(3) . . ? O9 C12 C11 124.9(3) . . ? O8 C12 C11 114.0(3) . . ? N4 C13 C14 123.8(3) . . ? N4 C13 H13A 118.1 . . ? C14 C13 H13A 118.1 . . ? C13 C14 C15 120.3(3) . . ? C13 C14 H14A 119.9 . . ? C15 C14 H14A 119.9 . . ? C14 C15 C16 116.2(2) . . ? C14 C15 C20 121.5(2) . . ? C16 C15 C20 122.3(2) . . ? C17 C16 C15 119.6(3) . . ? C17 C16 H16A 120.2 . . ? C15 C16 H16A 120.2 . . ? N4 C17 C16 123.9(3) . . ? N4 C17 H17A 118.0 . . ? C16 C17 H17A 118.0 . . ? N5 C18 C19 123.6(3) . . ? N5 C18 H18A 118.2 . . ? C19 C18 H18A 118.2 . . ? C18 C19 C20 119.9(3) . . ? C18 C19 H19A 120.1 . . ? C20 C19 H19A 120.1 . . ? C21 C20 C19 116.4(3) . . ? C21 C20 C15 122.4(2) . . ? C19 C20 C15 121.3(2) . . ? C22 C21 C20 119.9(3) . . ? C22 C21 H21A 120.0 . . ? C20 C21 H21A 120.0 . . ? N5 C22 C21 123.5(3) . . ? N5 C22 H22A 118.2 . . ? C21 C22 H22A 118.2 . . ? N6 C23 C24 123.0(3) . . ? N6 C23 H23A 118.5 . . ? C24 C23 H23A 118.5 . . ? C25 C24 C23 120.6(3) . . ? C25 C24 H24A 119.7 . . ? C23 C24 H24A 119.7 . . ? C24 C25 C26 116.8(2) . . ? C24 C25 C25 122.3(3) . 2_666 ? C26 C25 C25 120.9(3) . 2_666 ? C27 C26 C25 118.6(3) . . ? C27 C26 H26A 120.7 . . ? C25 C26 H26A 120.7 . . ? N6 C27 C26 123.8(3) . . ? N6 C27 H27A 118.1 . . ? C26 C27 H27A 118.1 . . ? C1 N1 C3 124.4(2) . . ? C1 N1 C4 117.9(2) . . ? C3 N1 C4 117.7(2) . . ? C2 N2 C1 124.2(2) . . ? C2 N2 C7 117.6(2) . . ? C1 N2 C7 118.2(2) . . ? C2 N3 C3 124.6(2) . . ? C2 N3 C10 117.0(2) . . ? C3 N3 C10 118.4(2) . . ? C17 N4 C13 116.2(2) . . ? C22 N5 C18 116.7(3) . . ? C23 N6 C27 117.1(2) . . ? C6 O5 H5C 109.5 . . ? C9 O7 H7C 109.5 . . ? C12 O8 H8C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C4 C5 C6 61.2(3) . . . . ? N2 C7 C8 C9 170.4(2) . . . . ? N3 C10 C11 C12 -170.5(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5C N4 0.82 1.92 2.703(3) 160.3 1_554 O7 H7C N5 0.82 1.87 2.671(3) 167.2 2_576 O8 H8C N6 0.82 1.82 2.633(3) 172.1 1_445 C4 H4A O2 0.97 2.68 3.023(3) 101.4 1_655 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.405 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.060 data_p2 #TrackingRef '- p1-3-r1.cif' _database_code_depnum_ccdc_archive 'CCDC 796380' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H21 N9 O9' _chemical_formula_weight 471.41 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 orthorhombic _symmetry_space_group_name_H-M pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.348(12) _cell_length_b 8.033(7) _cell_length_c 35.93(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4141(6) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 507 _cell_measurement_theta_min 4.535 _cell_measurement_theta_max 36.903 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1968 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9813 _exptl_absorpt_correction_T_max 0.9937 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16430 _diffrn_reflns_av_R_equivalents 0.1793 _diffrn_reflns_av_sigmaI/netI 0.1075 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 1.13 _diffrn_reflns_theta_max 23.31 _reflns_number_total 2969 _reflns_number_gt 1432 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0493P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2969 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1666 _refine_ls_R_factor_gt 0.0720 _refine_ls_wR_factor_ref 0.1513 _refine_ls_wR_factor_gt 0.1182 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3199(4) 0.3422(7) 0.57498(15) 0.0363(15) Uani 1 1 d . . . C2 C 0.3981(4) 0.1287(7) 0.61293(16) 0.0344(14) Uani 1 1 d . . . C3 C 0.3908(4) 0.0989(7) 0.54513(16) 0.0351(15) Uani 1 1 d . . . C4 C 0.3120(4) 0.3110(7) 0.50683(14) 0.0381(15) Uani 1 1 d . . . H4A H 0.2513 0.3639 0.5085 0.046 Uiso 1 1 calc R . . H4B H 0.3075 0.2192 0.4894 0.046 Uiso 1 1 calc R . . C5 C 0.3838(4) 0.4356(7) 0.49339(15) 0.0486(17) Uani 1 1 d . . . H5A H 0.3871 0.5260 0.5112 0.058 Uiso 1 1 calc R . . H5B H 0.4443 0.3815 0.4930 0.058 Uiso 1 1 calc R . . C6 C 0.3655(4) 0.5078(7) 0.45555(17) 0.0401(16) Uani 1 1 d . . . C7 C 0.3218(4) 0.3682(7) 0.64250(14) 0.0390(16) Uani 1 1 d . . . H7A H 0.3179 0.2926 0.6635 0.047 Uiso 1 1 calc R . . H7B H 0.2614 0.4207 0.6394 0.047 Uiso 1 1 calc R . . C8 C 0.3949(4) 0.5008(8) 0.65041(16) 0.0578(18) Uani 1 1 d . . . H8A H 0.4564 0.4532 0.6471 0.069 Uiso 1 1 calc R . . H8B H 0.3878 0.5909 0.6327 0.069 Uiso 1 1 calc R . . C9 C 0.3868(4) 0.5696(8) 0.68946(17) 0.0474(17) Uani 1 1 d . . . C10 C 0.4864(4) -0.0943(6) 0.58247(15) 0.0414(16) Uani 1 1 d . . . H10A H 0.4712 -0.1719 0.5627 0.050 Uiso 1 1 calc R . . H10B H 0.4771 -0.1507 0.6060 0.050 Uiso 1 1 calc R . . C11 C 0.5892(4) -0.0422(6) 0.57899(14) 0.0358(15) Uani 1 1 d . . . H11A H 0.6274 -0.1407 0.5758 0.043 Uiso 1 1 calc R . . H11B H 0.5968 0.0271 0.5571 0.043 Uiso 1 1 calc R . . C12 C 0.6219(4) 0.0521(7) 0.61276(15) 0.0357(14) Uani 1 1 d . . . C13 C 0.3597(4) 0.4587(7) 0.32104(16) 0.0348(15) Uani 1 1 d . . . C14 C 0.3785(4) 0.4648(7) 0.25886(15) 0.0390(15) Uani 1 1 d . . . C15 C 0.3674(4) 0.7142(7) 0.28906(17) 0.0379(15) Uani 1 1 d . . . O1 O 0.2804(3) 0.4758(5) 0.57264(10) 0.0527(12) Uani 1 1 d . . . O2 O 0.4197(3) 0.0775(5) 0.64346(10) 0.0522(12) Uani 1 1 d . . . O3 O 0.4074(3) 0.0171(5) 0.51743(10) 0.0478(11) Uani 1 1 d . . . O4 O 0.3095(3) 0.4532(5) 0.43385(11) 0.0561(12) Uani 1 1 d . . . O5 O 0.4203(3) 0.6352(5) 0.44837(11) 0.0742(15) Uani 1 1 d . . . H5C H 0.4044 0.6786 0.4287 0.111 Uiso 1 1 calc R . . O6 O 0.3785(3) 0.7310(5) 0.69021(10) 0.0657(14) Uani 1 1 d . . . H6A H 0.3731 0.7622 0.7118 0.098 Uiso 1 1 calc R . . O7 O 0.3902(4) 0.4816(5) 0.71644(11) 0.0731(15) Uani 1 1 d . . . O8 O 0.6180(3) 0.2115(4) 0.61206(9) 0.0430(10) Uani 1 1 d . . . O9 O 0.6484(3) -0.0295(4) 0.64036(10) 0.0428(11) Uani 1 1 d . . . N1 N 0.3405(3) 0.2483(5) 0.54390(11) 0.0315(11) Uani 1 1 d . . . N2 N 0.3449(3) 0.2742(5) 0.60885(12) 0.0318(12) Uani 1 1 d . . . N3 N 0.4229(3) 0.0521(5) 0.58026(11) 0.0314(11) Uani 1 1 d . . . N4 N 0.3582(3) 0.6296(5) 0.32175(11) 0.0359(12) Uani 1 1 d . . . H4C H 0.3516 0.6822 0.3424 0.043 Uiso 1 1 calc R . . N5 N 0.3707(3) 0.3720(5) 0.28999(13) 0.0372(12) Uani 1 1 d . . . N6 N 0.3753(3) 0.6341(5) 0.25676(11) 0.0379(12) Uani 1 1 d . . . N7 N 0.3528(3) 0.3804(5) 0.35373(12) 0.0425(13) Uani 1 1 d . . . H7C H 0.3555 0.2736 0.3547 0.051 Uiso 1 1 calc R . . H7D H 0.3456 0.4369 0.3739 0.051 Uiso 1 1 calc R . . N8 N 0.3886(3) 0.3827(5) 0.22716(12) 0.0561(15) Uani 1 1 d . . . H8C H 0.3899 0.2756 0.2272 0.067 Uiso 1 1 calc R . . H8D H 0.3938 0.4363 0.2066 0.067 Uiso 1 1 calc R . . N9 N 0.3680(3) 0.8772(5) 0.29035(12) 0.0460(13) Uani 1 1 d . . . H9A H 0.3734 0.9339 0.2702 0.055 Uiso 1 1 calc R . . H9B H 0.3628 0.9275 0.3114 0.055 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.041(4) 0.032(4) 0.036(4) -0.003(3) 0.007(3) -0.008(3) C2 0.041(4) 0.028(3) 0.034(4) -0.002(3) 0.006(3) -0.004(3) C3 0.030(4) 0.043(4) 0.032(4) -0.006(3) -0.001(3) -0.007(3) C4 0.042(4) 0.047(4) 0.026(3) 0.000(3) -0.002(3) -0.006(3) C5 0.056(4) 0.057(4) 0.034(4) 0.022(3) -0.012(3) -0.015(4) C6 0.042(4) 0.038(4) 0.041(4) 0.006(3) 0.001(3) -0.001(3) C7 0.049(4) 0.046(4) 0.021(3) -0.002(3) -0.002(3) 0.011(3) C8 0.078(5) 0.049(4) 0.046(4) -0.012(3) 0.008(4) -0.014(4) C9 0.069(5) 0.038(4) 0.036(4) -0.011(3) -0.004(4) -0.005(4) C10 0.060(5) 0.023(3) 0.041(4) -0.003(3) -0.007(3) 0.000(3) C11 0.040(4) 0.032(3) 0.036(4) 0.001(3) 0.002(3) 0.008(3) C12 0.041(4) 0.040(4) 0.027(3) -0.004(3) 0.005(3) 0.002(4) C13 0.034(4) 0.034(4) 0.037(4) 0.001(3) -0.003(3) 0.001(3) C14 0.059(4) 0.027(3) 0.031(4) -0.002(3) -0.002(3) 0.003(4) C15 0.047(4) 0.026(3) 0.041(4) 0.006(3) -0.006(3) 0.003(3) O1 0.068(3) 0.048(3) 0.043(3) -0.004(2) -0.009(2) 0.029(2) O2 0.080(3) 0.050(3) 0.027(2) 0.007(2) -0.003(2) 0.010(2) O3 0.061(3) 0.054(3) 0.029(2) -0.011(2) 0.003(2) 0.008(2) O4 0.070(3) 0.056(3) 0.043(3) 0.009(2) -0.014(2) -0.017(3) O5 0.100(4) 0.069(3) 0.053(3) 0.035(2) -0.037(3) -0.039(3) O6 0.126(4) 0.036(3) 0.035(3) -0.007(2) -0.012(3) 0.008(3) O7 0.152(5) 0.032(3) 0.035(3) 0.000(2) -0.007(3) -0.001(3) O8 0.072(3) 0.026(2) 0.031(2) 0.0047(18) -0.005(2) 0.001(2) O9 0.069(3) 0.032(2) 0.026(2) 0.0064(18) -0.007(2) 0.003(2) N1 0.044(3) 0.028(3) 0.023(3) -0.004(2) -0.003(2) 0.000(2) N2 0.039(3) 0.035(3) 0.021(3) -0.002(2) 0.002(2) 0.000(2) N3 0.042(3) 0.028(3) 0.024(3) -0.004(2) -0.006(2) 0.002(2) N4 0.059(3) 0.023(3) 0.026(3) -0.001(2) 0.006(2) 0.000(3) N5 0.059(3) 0.023(2) 0.029(3) 0.000(2) 0.001(3) -0.002(3) N6 0.059(4) 0.027(3) 0.027(3) -0.002(2) -0.007(2) 0.001(3) N7 0.071(4) 0.025(3) 0.031(3) -0.003(2) 0.004(3) -0.002(3) N8 0.110(5) 0.032(3) 0.026(3) -0.002(2) -0.002(3) -0.003(3) N9 0.085(4) 0.025(3) 0.028(3) 0.001(2) 0.001(3) 0.002(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.216(6) . ? C1 N1 1.380(6) . ? C1 N2 1.382(6) . ? C2 O2 1.212(6) . ? C2 N3 1.372(6) . ? C2 N2 1.403(6) . ? C3 O3 1.216(6) . ? C3 N3 1.395(6) . ? C3 N1 1.401(6) . ? C4 N1 1.482(6) . ? C4 C5 1.516(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.501(7) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O4 1.203(6) . ? C6 O5 1.316(6) . ? C7 N2 1.463(6) . ? C7 C8 1.521(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.512(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 O7 1.201(6) . ? C9 O6 1.302(6) . ? C10 N3 1.490(6) . ? C10 C11 1.538(7) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.506(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 O9 1.248(6) . ? C12 O8 1.283(6) . ? C13 N5 1.325(6) . ? C13 N7 1.336(6) . ? C13 N4 1.373(6) . ? C14 N8 1.324(6) . ? C14 N5 1.349(6) . ? C14 N6 1.363(6) . ? C15 N9 1.311(6) . ? C15 N6 1.332(6) . ? C15 N4 1.364(6) . ? O5 H5C 0.8200 . ? O6 H6A 0.8200 . ? N4 H4C 0.8600 . ? N7 H7C 0.8600 . ? N7 H7D 0.8600 . ? N8 H8C 0.8600 . ? N8 H8D 0.8600 . ? N9 H9A 0.8600 . ? N9 H9B 0.8600 . ? 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 O1 C1 N1 121.8(5) . . ? O1 C1 N2 122.1(5) . . ? N1 C1 N2 116.2(5) . . ? O2 C2 N3 123.7(5) . . ? O2 C2 N2 121.1(5) . . ? N3 C2 N2 115.2(5) . . ? O3 C3 N3 122.0(5) . . ? O3 C3 N1 122.5(5) . . ? N3 C3 N1 115.4(5) . . ? N1 C4 C5 108.8(4) . . ? N1 C4 H4A 109.9 . . ? C5 C4 H4A 109.9 . . ? N1 C4 H4B 109.9 . . ? C5 C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? C6 C5 C4 115.2(5) . . ? C6 C5 H5A 108.5 . . ? C4 C5 H5A 108.5 . . ? C6 C5 H5B 108.5 . . ? C4 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? O4 C6 O5 123.8(6) . . ? O4 C6 C5 124.2(6) . . ? O5 C6 C5 112.0(5) . . ? N2 C7 C8 111.1(4) . . ? N2 C7 H7A 109.4 . . ? C8 C7 H7A 109.4 . . ? N2 C7 H7B 109.4 . . ? C8 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? C9 C8 C7 112.1(5) . . ? C9 C8 H8A 109.2 . . ? C7 C8 H8A 109.2 . . ? C9 C8 H8B 109.2 . . ? C7 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? O7 C9 O6 124.9(6) . . ? O7 C9 C8 122.0(6) . . ? O6 C9 C8 113.0(6) . . ? N3 C10 C11 111.5(4) . . ? N3 C10 H10A 109.3 . . ? C11 C10 H10A 109.3 . . ? N3 C10 H10B 109.3 . . ? C11 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? C12 C11 C10 111.7(4) . . ? C12 C11 H11A 109.3 . . ? C10 C11 H11A 109.3 . . ? C12 C11 H11B 109.3 . . ? C10 C11 H11B 109.3 . . ? H11A C11 H11B 107.9 . . ? O9 C12 O8 123.6(5) . . ? O9 C12 C11 118.1(5) . . ? O8 C12 C11 118.2(5) . . ? N5 C13 N7 120.1(5) . . ? N5 C13 N4 122.9(5) . . ? N7 C13 N4 116.9(5) . . ? N8 C14 N5 116.5(5) . . ? N8 C14 N6 117.0(5) . . ? N5 C14 N6 126.5(5) . . ? N9 C15 N6 120.9(5) . . ? N9 C15 N4 117.9(5) . . ? N6 C15 N4 121.2(5) . . ? C6 O5 H5C 109.5 . . ? C9 O6 H6A 109.5 . . ? C1 N1 C3 123.6(5) . . ? C1 N1 C4 118.8(5) . . ? C3 N1 C4 117.5(4) . . ? C1 N2 C2 124.2(5) . . ? C1 N2 C7 117.7(5) . . ? C2 N2 C7 117.8(4) . . ? C2 N3 C3 124.6(5) . . ? C2 N3 C10 117.9(4) . . ? C3 N3 C10 117.6(4) . . ? C15 N4 C13 118.7(5) . . ? C15 N4 H4C 120.6 . . ? C13 N4 H4C 120.6 . . ? C13 N5 C14 114.7(4) . . ? C15 N6 C14 115.9(5) . . ? C13 N7 H7C 120.0 . . ? C13 N7 H7D 120.0 . . ? H7C N7 H7D 120.0 . . ? C14 N8 H8C 120.0 . . ? C14 N8 H8D 120.0 . . ? H8C N8 H8D 120.0 . . ? C15 N9 H9A 120.0 . . ? C15 N9 H9B 120.0 . . ? H9A N9 H9B 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C4 C5 C6 178.7(5) . . . . ? N2 C7 C8 C9 -165.5(5) . . . . ? N3 C10 C11 C12 69.7(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5C O8 0.82 1.74 2.556(5) 172.8 5_666 O6 H6A N6 0.82 1.82 2.625(6) 168.7 7_576 N4 H4C O8 0.86 1.90 2.720(6) 160.2 5_666 N7 H7C O9 0.86 1.97 2.827(6) 174.8 5_656 N7 H7D O4 0.86 2.22 3.002(6) 151.1 . N8 H8C O7 0.86 2.10 2.952(6) 169.3 7_565 N8 H8D O2 0.86 2.30 3.057(6) 147.0 7_565 N9 H9A O7 0.86 2.06 2.905(6) 167.2 7_575 N9 H9B O9 0.86 1.92 2.784(6) 177.2 5_666 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 23.31 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.236 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.057 # Attachment '- p1-3-r1.cif' #TrackingRef '- p1-3-r1.cif' #==================================================================== data_p1 #TrackingRef '- p1-3-r1.cif' _database_code_depnum_ccdc_archive 'CCDC 796381' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H15 N3 O9' _chemical_formula_weight 345.27 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 p2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.6775(7) _cell_length_b 15.7719(12) _cell_length_c 10.9612(8) _cell_angle_alpha 90.00 _cell_angle_beta 96.0660(10) _cell_angle_gamma 90.00 _cell_volume 1491.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3492 _cell_measurement_theta_min 4.543 _cell_measurement_theta_max 54.608 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9738 _exptl_absorpt_correction_T_max 0.9868 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7268 _diffrn_reflns_av_R_equivalents 0.0168 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2621 _reflns_number_gt 2262 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0540P)^2^+0.5636P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0033(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2621 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0466 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.1121 _refine_ls_wR_factor_gt 0.1062 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.73077(18) 0.01817(10) 0.69296(14) 0.0339(4) Uani 1 1 d . . . C2 C 0.76322(19) 0.17234(10) 0.70736(15) 0.0345(4) Uani 1 1 d . . . C3 C 0.80761(19) 0.08478(11) 0.88970(14) 0.0358(4) Uani 1 1 d . . . C4 C 0.7845(2) -0.06869(11) 0.87921(16) 0.0410(4) Uani 1 1 d . . . H4A H 0.8776 -0.0708 0.9365 0.049 Uiso 1 1 calc R . . H4B H 0.7924 -0.1127 0.8183 0.049 Uiso 1 1 calc R . . C5 C 0.6447(2) -0.08657(12) 0.94788(16) 0.0434(4) Uani 1 1 d . . . H5A H 0.5797 -0.0364 0.9440 0.052 Uiso 1 1 calc R . . H5B H 0.5849 -0.1319 0.9061 0.052 Uiso 1 1 calc R . . C6 C 0.68223(19) -0.11070(11) 1.07861(15) 0.0392(4) Uani 1 1 d . . . C7 C 0.6795(2) 0.10592(11) 0.50972(14) 0.0371(4) Uani 1 1 d . . . H7A H 0.6411 0.1627 0.4907 0.044 Uiso 1 1 calc R . . H7B H 0.5968 0.0661 0.4851 0.044 Uiso 1 1 calc R . . C8 C 0.8145(2) 0.08817(16) 0.43990(16) 0.0581(6) Uani 1 1 d . . . H8A H 0.8989 0.1258 0.4690 0.070 Uiso 1 1 calc R . . H8B H 0.8492 0.0304 0.4566 0.070 Uiso 1 1 calc R . . C9 C 0.7795(2) 0.09910(17) 0.30502(17) 0.0596(6) Uani 1 1 d . . . C10 C 0.8466(2) 0.23711(12) 0.90838(16) 0.0436(4) Uani 1 1 d . . . H10A H 0.8834 0.2818 0.8580 0.052 Uiso 1 1 calc R . . H10B H 0.9293 0.2230 0.9717 0.052 Uiso 1 1 calc R . . C11 C 0.7066(2) 0.26855(12) 0.96774(17) 0.0456(4) Uani 1 1 d . . . H11A H 0.6484 0.3072 0.9115 0.055 Uiso 1 1 calc R . . H11B H 0.6401 0.2205 0.9801 0.055 Uiso 1 1 calc R . . C12 C 0.7444(2) 0.31250(11) 1.08758(16) 0.0416(4) Uani 1 1 d . . . O1 O 0.69904(17) -0.04416(8) 0.63164(11) 0.0533(4) Uani 1 1 d . . . O2 O 0.75848(18) 0.24076(8) 0.65907(12) 0.0548(4) Uani 1 1 d . . . O3 O 0.83623(16) 0.07838(9) 1.00058(10) 0.0526(4) Uani 1 1 d . . . O4 O 0.81440(15) -0.12289(11) 1.12639(12) 0.0622(4) Uani 1 1 d . . . O5 O 0.56036(15) -0.11847(11) 1.13747(12) 0.0634(4) Uani 1 1 d . . . H5C H 0.5861 -0.1373 1.2063 0.095 Uiso 1 1 calc R . . O6' O 0.8984(9) 0.0870(5) 0.2470(6) 0.109(3) Uani 0.70 1 d P . . H6B H 0.8889 0.1131 0.1820 0.164 Uiso 0.70 1 calc PR . . O6 O 0.8709(19) 0.0560(9) 0.2405(16) 0.083(5) Uani 0.30 1 d P . . H6A H 0.8299 0.0520 0.1698 0.124 Uiso 0.30 1 calc PR . . O7 O 0.6704(4) 0.1404(3) 0.2572(3) 0.0881(11) Uani 0.70 1 d P . . O7' O 0.6542(8) 0.0750(7) 0.2543(6) 0.102(3) Uani 0.30 1 d P . . O8 O 0.87693(16) 0.32091(11) 1.13651(13) 0.0638(4) Uani 1 1 d . . . O9 O 0.62381(16) 0.34022(11) 1.13572(13) 0.0683(5) Uani 1 1 d . . . H9A H 0.6476 0.3508 1.2085 0.102 Uiso 1 1 calc R . . N1 N 0.77530(16) 0.01462(8) 0.81774(11) 0.0345(3) Uani 1 1 d . . . N2 N 0.72404(15) 0.09854(8) 0.64291(11) 0.0323(3) Uani 1 1 d . . . N3 N 0.80690(16) 0.16161(8) 0.83165(12) 0.0357(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0417(9) 0.0355(9) 0.0247(8) -0.0002(6) 0.0051(6) -0.0019(7) C2 0.0394(9) 0.0343(9) 0.0301(8) -0.0016(7) 0.0057(7) 0.0014(7) C3 0.0382(9) 0.0468(10) 0.0228(8) -0.0030(7) 0.0044(6) 0.0048(7) C4 0.0515(10) 0.0404(9) 0.0328(9) 0.0109(7) 0.0116(7) 0.0112(8) C5 0.0440(10) 0.0520(11) 0.0343(9) 0.0111(8) 0.0046(8) 0.0067(8) C6 0.0395(9) 0.0444(10) 0.0341(9) 0.0084(7) 0.0056(7) -0.0026(7) C7 0.0435(9) 0.0458(9) 0.0209(8) 0.0031(7) -0.0015(6) 0.0003(7) C8 0.0474(11) 0.1018(17) 0.0247(9) 0.0019(9) 0.0019(8) 0.0052(11) C9 0.0478(11) 0.1051(18) 0.0258(9) 0.0009(10) 0.0032(8) -0.0011(12) C10 0.0465(10) 0.0467(10) 0.0378(9) -0.0177(8) 0.0050(8) -0.0064(8) C11 0.0434(10) 0.0519(11) 0.0408(10) -0.0183(8) 0.0011(8) 0.0010(8) C12 0.0425(10) 0.0489(10) 0.0337(9) -0.0087(7) 0.0057(7) 0.0003(8) O1 0.0864(10) 0.0372(7) 0.0347(7) -0.0056(5) -0.0004(6) -0.0111(6) O2 0.0830(10) 0.0320(7) 0.0488(8) 0.0048(6) 0.0045(7) 0.0001(6) O3 0.0670(9) 0.0700(9) 0.0201(6) -0.0025(6) 0.0007(6) 0.0079(7) O4 0.0415(7) 0.1054(12) 0.0398(7) 0.0291(8) 0.0049(6) 0.0055(7) O5 0.0419(7) 0.1097(12) 0.0393(7) 0.0285(8) 0.0072(6) 0.0002(8) O6' 0.0573(17) 0.248(9) 0.0233(16) -0.006(4) 0.0105(12) -0.002(4) O6 0.101(12) 0.113(7) 0.034(4) -0.001(4) 0.005(6) 0.052(8) O7 0.087(2) 0.142(3) 0.0353(13) 0.0207(19) 0.0044(13) 0.038(2) O7' 0.044(3) 0.228(10) 0.031(3) -0.005(5) -0.007(2) -0.005(6) O8 0.0426(8) 0.1057(12) 0.0432(8) -0.0316(8) 0.0050(6) -0.0047(7) O9 0.0485(8) 0.1129(13) 0.0423(8) -0.0314(8) -0.0003(6) 0.0174(8) N1 0.0470(8) 0.0347(7) 0.0221(6) 0.0024(5) 0.0059(6) 0.0045(6) N2 0.0423(8) 0.0335(7) 0.0208(7) 0.0000(5) 0.0020(5) 0.0001(6) N3 0.0430(8) 0.0373(8) 0.0269(7) -0.0083(6) 0.0038(6) -0.0010(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 C1 O1 1.2063(19) . ? C1 N2 1.380(2) . ? C1 N1 1.383(2) . ? C2 O2 1.201(2) . ? C2 N2 1.385(2) . ? C2 N3 1.385(2) . ? C3 O3 1.219(2) . ? C3 N3 1.368(2) . ? C3 N1 1.371(2) . ? C4 N1 1.475(2) . ? C4 C5 1.520(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.485(2) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O4 1.225(2) . ? C6 O5 1.301(2) . ? C7 N2 1.4748(19) . ? C7 C8 1.492(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.488(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 O7 1.220(4) . ? C9 O7' 1.228(7) . ? C9 O6' 1.283(7) . ? C9 O6 1.308(15) . ? C10 N3 1.477(2) . ? C10 C11 1.520(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.491(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 O8 1.223(2) . ? C12 O9 1.297(2) . ? O5 H5C 0.8200 . ? O6' O6 0.55(2) . ? O6' H6B 0.8200 . ? O6 H6A 0.8200 . ? O7 O7' 1.041(10) . ? O9 H9A 0.8200 . ? 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 O1 C1 N2 121.97(14) . . ? O1 C1 N1 122.80(14) . . ? N2 C1 N1 115.23(13) . . ? O2 C2 N2 122.36(15) . . ? O2 C2 N3 122.43(15) . . ? N2 C2 N3 115.20(14) . . ? O3 C3 N3 121.83(15) . . ? O3 C3 N1 120.99(16) . . ? N3 C3 N1 117.18(13) . . ? N1 C4 C5 112.60(13) . . ? N1 C4 H4A 109.1 . . ? C5 C4 H4A 109.1 . . ? N1 C4 H4B 109.1 . . ? C5 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? C6 C5 C4 114.86(14) . . ? C6 C5 H5A 108.6 . . ? C4 C5 H5A 108.6 . . ? C6 C5 H5B 108.6 . . ? C4 C5 H5B 108.6 . . ? H5A C5 H5B 107.5 . . ? O4 C6 O5 123.13(15) . . ? O4 C6 C5 123.56(15) . . ? O5 C6 C5 113.31(15) . . ? N2 C7 C8 110.81(14) . . ? N2 C7 H7A 109.5 . . ? C8 C7 H7A 109.5 . . ? N2 C7 H7B 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C9 C8 C7 113.50(16) . . ? C9 C8 H8A 108.9 . . ? C7 C8 H8A 108.9 . . ? C9 C8 H8B 108.9 . . ? C7 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? O7 C9 O7' 50.3(5) . . ? O7 C9 O6' 119.7(4) . . ? O7' C9 O6' 116.7(5) . . ? O7 C9 O6 122.1(7) . . ? O7' C9 O6 98.8(9) . . ? O7 C9 C8 123.8(2) . . ? O7' C9 C8 119.5(4) . . ? O6' C9 C8 112.6(4) . . ? O6 C9 C8 113.9(7) . . ? N3 C10 C11 110.97(14) . . ? N3 C10 H10A 109.4 . . ? C11 C10 H10A 109.4 . . ? N3 C10 H10B 109.4 . . ? C11 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C12 C11 C10 114.68(15) . . ? C12 C11 H11A 108.6 . . ? C10 C11 H11A 108.6 . . ? C12 C11 H11B 108.6 . . ? C10 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? O8 C12 O9 123.14(16) . . ? O8 C12 C11 123.08(16) . . ? O9 C12 C11 113.78(15) . . ? C6 O5 H5C 109.5 . . ? O6 O6' C9 81(2) . . ? O6 O6' H6B 109.5 . . ? C9 O6' H6B 110.1 . . ? O6' O6 C9 75(2) . . ? O6' O6 H6A 109.5 . . ? C9 O6 H6A 108.8 . . ? O7' O7 C9 65.2(4) . . ? O7 O7' C9 64.5(5) . . ? C12 O9 H9A 109.5 . . ? C3 N1 C1 123.74(13) . . ? C3 N1 C4 117.29(13) . . ? C1 N1 C4 118.95(13) . . ? C1 N2 C2 124.84(13) . . ? C1 N2 C7 117.50(13) . . ? C2 N2 C7 117.58(13) . . ? C3 N3 C2 123.56(13) . . ? C3 N3 C10 117.37(14) . . ? C2 N3 C10 118.98(14) . . ? 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 N1 C4 C5 C6 -126.93(17) . . . . ? N2 C7 C8 C9 -176.90(18) . . . . ? N3 C10 C11 C12 151.17(16) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5C O8 0.82 1.84 2.6577(18) 174.2 2_647 O6 H6A O3 0.82 1.91 2.639(17) 148.0 1_554 O9 H9A O4 0.82 1.85 2.6701(18) 175.6 2_657 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.201 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.036