# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Seetha Lekshmi Sunil' _publ_contact_author_email seetha208@yahoo.co.uk _publ_author_name 'Seetha Lekshmi Sunil' data_1 _database_code_depnum_ccdc_archive 'CCDC 782608' #TrackingRef '23DHB.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; 3(C7 H5 O4), 3(C3 H7 N6), 11(O)' ; _chemical_formula_sum 'C30 H36 N18 O23' _chemical_formula_weight 1016.77 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 10.8110(10) _cell_length_b 12.2980(10) _cell_length_c 19.5800(10) _cell_angle_alpha 82.230(4) _cell_angle_beta 79.120(5) _cell_angle_gamma 64.530(5) _cell_volume 2303.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2703 _cell_measurement_theta_min 4.367 _cell_measurement_theta_max 46.163 _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1052 _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9774 _exptl_absorpt_correction_T_max 0.9861 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 43060 _diffrn_reflns_av_R_equivalents 0.0794 _diffrn_reflns_av_sigmaI/netI 0.0873 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.24 _reflns_number_total 8323 _reflns_number_gt 4456 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlisPro RED (Oxford Diffraction, 2009)' _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^)+(0.1061P)^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 SHELXL _refine_ls_extinction_coef ? _refine_ls_number_reflns 8323 _refine_ls_number_parameters 640 _refine_ls_number_restraints 569 _refine_ls_R_factor_all 0.1432 _refine_ls_R_factor_gt 0.0797 _refine_ls_wR_factor_ref 0.2257 _refine_ls_wR_factor_gt 0.2058 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.076 _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 O22 O 0.6799(3) 0.3890(3) 0.16799(16) 0.0315(8) Uani 1 1 d U . . H22 H 0.6501 0.3778 0.2100 0.047 Uiso 1 1 calc R . . O23 O 0.7804(3) 0.3948(3) 0.03530(16) 0.0344(8) Uani 1 1 d U . . H23 H 0.8155 0.3873 -0.0068 0.052 Uiso 1 1 calc R . . O27A O 0.6296(3) 0.2669(3) 0.27793(15) 0.0326(8) Uani 1 1 d U . . O27B O 0.7054(3) 0.0681(3) 0.27850(15) 0.0304(8) Uani 1 1 d U . . C21 C 0.7438(4) 0.1742(4) 0.1710(2) 0.0210(10) Uani 1 1 d U . . C22 C 0.7371(4) 0.2820(4) 0.1364(2) 0.0231(10) Uani 1 1 d U . . C23 C 0.7902(5) 0.2851(4) 0.0658(2) 0.0261(11) Uani 1 1 d U . . C24 C 0.8496(4) 0.1805(4) 0.0306(2) 0.0250(10) Uani 1 1 d U . . H24A H 0.8861 0.1827 -0.0174 0.030 Uiso 1 1 calc R . . C25 C 0.8564(4) 0.0710(4) 0.0651(2) 0.0265(11) Uani 1 1 d U . . H25A H 0.8962 -0.0006 0.0405 0.032 Uiso 1 1 calc R . . C26 C 0.8054(4) 0.0678(4) 0.1344(2) 0.0238(10) Uani 1 1 d U . . H26A H 0.8114 -0.0066 0.1581 0.029 Uiso 1 1 calc R . . C27 C 0.6897(5) 0.1691(4) 0.2463(2) 0.0278(11) Uani 1 1 d U . . O32 O 0.0176(3) 0.4147(3) 0.14951(16) 0.0318(8) Uani 1 1 d U . . H32 H -0.0124 0.4062 0.1918 0.048 Uiso 1 1 calc R . . O33 O 0.1234(3) 0.4063(3) 0.01381(17) 0.0360(9) Uani 1 1 d U . . H33 H 0.1611 0.3910 -0.0275 0.054 Uiso 1 1 calc R . . O37A O -0.0393(3) 0.3012(3) 0.26354(16) 0.0364(8) Uani 1 1 d U . . O37B O 0.0409(3) 0.1019(3) 0.27034(16) 0.0337(8) Uani 1 1 d U . . C31 C 0.0784(4) 0.2000(4) 0.1600(2) 0.0228(10) Uani 1 1 d U . . C32 C 0.0725(4) 0.3067(4) 0.1204(2) 0.0231(10) Uani 1 1 d U . . C33 C 0.1274(4) 0.3014(4) 0.0510(2) 0.0221(10) Uani 1 1 d U . . C34 C 0.1868(5) 0.1929(4) 0.0197(2) 0.0274(11) Uani 1 1 d U . . H34A H 0.2227 0.1901 -0.0285 0.033 Uiso 1 1 calc R . . C35 C 0.1940(5) 0.0876(4) 0.0587(2) 0.0275(11) Uani 1 1 d U . . H35A H 0.2365 0.0129 0.0371 0.033 Uiso 1 1 calc R . . C36 C 0.1412(4) 0.0908(4) 0.1267(2) 0.0242(10) Uani 1 1 d U . . H36A H 0.1465 0.0182 0.1526 0.029 Uiso 1 1 calc R . . C37 C 0.0229(5) 0.2007(4) 0.2353(2) 0.0257(11) Uani 1 1 d U . . N51 N 0.8736(3) 0.4508(3) 0.40519(18) 0.0212(8) Uani 1 1 d U . . H51A H 0.8593 0.5144 0.4268 0.025 Uiso 1 1 calc R . . H51B H 0.9013 0.4484 0.3600 0.025 Uiso 1 1 calc R . . N52 N 0.8118(3) 0.3604(3) 0.50867(18) 0.0185(8) Uani 1 1 d U . . N53 N 0.7499(4) 0.2627(3) 0.60773(18) 0.0226(9) Uani 1 1 d U . . H53A H 0.7346 0.3250 0.6308 0.027 Uiso 1 1 calc R . . H53B H 0.7365 0.2005 0.6298 0.027 Uiso 1 1 calc R . . N54 N 0.8184(3) 0.1622(3) 0.50720(18) 0.0187(8) Uani 1 1 d U . . N55 N 0.8921(4) 0.0712(3) 0.40283(19) 0.0242(9) Uani 1 1 d U . . H55A H 0.8828 0.0063 0.4233 0.029 Uiso 1 1 calc R . . H55B H 0.9213 0.0743 0.3578 0.029 Uiso 1 1 calc R . . N56 N 0.8811(3) 0.2609(3) 0.40435(18) 0.0198(8) Uani 1 1 d DU . . H56 H 0.9103 0.2606 0.3592 0.024 Uiso 1 1 calc RD . . C51 C 0.8533(4) 0.3586(4) 0.4409(2) 0.0177(9) Uani 1 1 d U . . C53 C 0.7930(4) 0.2626(4) 0.5398(2) 0.0187(10) Uani 1 1 d U . . C55 C 0.8622(4) 0.1642(3) 0.4399(2) 0.0168(9) Uani 1 1 d U . . N61 N 0.5385(3) 0.4409(3) 0.41326(18) 0.0207(8) Uani 1 1 d U . . H61A H 0.5244 0.5052 0.4340 0.025 Uiso 1 1 calc R . . H61B H 0.5670 0.4366 0.3681 0.025 Uiso 1 1 calc R . . N62 N 0.4742(3) 0.3553(3) 0.51739(18) 0.0178(8) Uani 1 1 d U . . N63 N 0.4121(4) 0.2610(3) 0.61751(18) 0.0228(9) Uani 1 1 d U . . H63A H 0.3996 0.1995 0.6412 0.027 Uiso 1 1 calc R . . H63B H 0.3963 0.3251 0.6390 0.027 Uiso 1 1 calc R . . N64 N 0.4778(3) 0.1576(3) 0.51818(18) 0.0184(8) Uani 1 1 d U . . N65 N 0.5544(3) 0.0630(3) 0.41473(19) 0.0226(9) Uani 1 1 d U . . H65A H 0.5440 -0.0010 0.4359 0.027 Uiso 1 1 calc R . . H65B H 0.5850 0.0642 0.3698 0.027 Uiso 1 1 calc R . . N66 N 0.5440(3) 0.2528(3) 0.41444(18) 0.0180(8) Uani 1 1 d U . . H66 H 0.5736 0.2517 0.3694 0.022 Uiso 1 1 calc R . . C61 C 0.5168(4) 0.3503(4) 0.4500(2) 0.0170(9) Uani 1 1 d U . . C63 C 0.4544(4) 0.2571(3) 0.5498(2) 0.0168(9) Uani 1 1 d U . . C65 C 0.5242(4) 0.1568(4) 0.4502(2) 0.0179(10) Uani 1 1 d U . . N41 N 0.2169(4) 0.0542(3) 0.42449(19) 0.0254(9) Uani 1 1 d U . . H41A H 0.2056 -0.0091 0.4464 0.030 Uiso 1 1 calc R . . H41B H 0.2485 0.0537 0.3797 0.030 Uiso 1 1 calc R . . N42 N 0.2058(4) 0.2452(3) 0.42138(18) 0.0210(8) Uani 1 1 d DU . . H42 H 0.2342 0.2422 0.3762 0.025 Uiso 1 1 calc RD . . N43 N 0.2043(3) 0.4327(3) 0.41761(18) 0.0217(8) Uani 1 1 d U . . H43A H 0.1909 0.4977 0.4374 0.026 Uiso 1 1 calc R . . H43B H 0.2337 0.4264 0.3726 0.026 Uiso 1 1 calc R . . N44 N 0.1365(3) 0.3513(3) 0.52281(18) 0.0181(8) Uani 1 1 d U . . N45 N 0.0667(4) 0.2615(3) 0.62292(18) 0.0243(9) Uani 1 1 d U . . H45A H 0.0510 0.2014 0.6465 0.029 Uiso 1 1 calc R . . H45B H 0.0501 0.3262 0.6441 0.029 Uiso 1 1 calc R . . N46 N 0.1388(4) 0.1533(3) 0.52575(18) 0.0204(8) Uani 1 1 d U . . C41 C 0.1858(4) 0.1509(4) 0.4593(2) 0.0197(10) Uani 1 1 d U . . C43 C 0.1805(4) 0.3445(3) 0.4554(2) 0.0175(9) Uani 1 1 d U . . C45 C 0.1148(4) 0.2548(3) 0.5562(2) 0.0181(10) Uani 1 1 d U . . O12 O 0.4145(3) 0.0579(3) 0.19976(16) 0.0329(8) Uani 1 1 d U . . H12 H 0.3802 0.0838 0.2397 0.049 Uiso 1 1 calc R . . O13 O 0.5178(3) 0.0068(3) 0.06715(16) 0.0340(8) Uani 1 1 d U . . H13 H 0.5036 -0.0359 0.1024 0.051 Uiso 1 1 calc R . . O17A O 0.3106(3) 0.2079(3) 0.29089(16) 0.0377(9) Uani 1 1 d U . . O17B O 0.2764(3) 0.4012(3) 0.26778(16) 0.0328(8) Uani 1 1 d U . . C11 C 0.3801(4) 0.2657(4) 0.1751(2) 0.0234(10) Uani 1 1 d U . . C12 C 0.4251(4) 0.1491(4) 0.1545(2) 0.0222(10) Uani 1 1 d U . . C13 C 0.4793(4) 0.1230(4) 0.0861(2) 0.0251(10) Uani 1 1 d U . . C14 C 0.4916(5) 0.2105(4) 0.0379(2) 0.0284(11) Uani 1 1 d U . . H14A H 0.5286 0.1917 -0.0092 0.034 Uiso 1 1 calc R . . C15 C 0.4494(5) 0.3285(4) 0.0579(2) 0.0285(11) Uani 1 1 d U . . H15A H 0.4583 0.3896 0.0247 0.034 Uiso 1 1 calc R . . C16 C 0.3956(4) 0.3534(4) 0.1257(2) 0.0247(10) Uani 1 1 d U . . H16A H 0.3679 0.4326 0.1395 0.030 Uiso 1 1 calc R . . C17 C 0.3195(5) 0.2942(4) 0.2488(2) 0.0282(11) Uani 1 1 d U . . O94 O 0.0108(3) 0.4474(3) 0.71629(15) 0.0319(8) Uani 1 1 d U . . O95 O 0.1624(3) 0.3065(3) 0.82114(17) 0.0415(9) Uani 1 1 d U . . O97 O 0.1007(4) 0.6169(3) 0.10394(16) 0.0393(9) Uani 1 1 d U . . O96 O 0.5603(4) 0.1829(3) 0.84623(17) 0.0420(9) Uani 1 1 d U . . O99 O 0.2035(4) 0.7511(3) 0.17133(18) 0.0457(10) Uani 1 1 d U . . O92 O 0.3540(3) 0.1162(3) 0.74326(17) 0.0344(8) Uani 1 1 d U . . O91 O 0.7081(3) 0.0789(3) 0.70529(17) 0.0375(9) Uani 1 1 d U . . O90 O 0.3804(4) 0.4448(3) 0.71384(17) 0.0454(10) Uani 1 1 d U . . O100 O 0.3585(4) 0.5831(3) 0.26999(17) 0.0451(10) Uani 1 1 d U . . O93 O 0.9868(3) -0.0945(3) 0.26479(16) 0.0333(8) Uani 1 1 d U . . O98 O 0.3116(3) 0.3845(3) 0.88838(16) 0.0348(8) Uani 1 1 d U . . 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 O22 0.038(2) 0.0208(17) 0.0309(19) -0.0049(14) 0.0049(15) -0.0103(16) O23 0.040(2) 0.0259(18) 0.0307(19) -0.0016(15) 0.0068(15) -0.0125(16) O27A 0.041(2) 0.0244(18) 0.0273(19) -0.0090(14) 0.0048(15) -0.0105(16) O27B 0.036(2) 0.0227(18) 0.0306(19) -0.0028(14) 0.0018(15) -0.0130(16) C21 0.015(2) 0.019(2) 0.026(2) -0.0061(18) 0.0027(19) -0.005(2) C22 0.018(3) 0.019(2) 0.033(3) -0.0043(19) -0.005(2) -0.007(2) C23 0.022(3) 0.021(2) 0.029(3) -0.001(2) -0.002(2) -0.005(2) C24 0.017(3) 0.031(3) 0.023(2) -0.004(2) -0.0011(19) -0.006(2) C25 0.017(3) 0.025(3) 0.030(3) -0.006(2) -0.001(2) -0.001(2) C26 0.020(3) 0.016(2) 0.032(3) 0.0010(19) -0.005(2) -0.005(2) C27 0.026(3) 0.025(3) 0.033(3) -0.002(2) -0.003(2) -0.012(2) O32 0.031(2) 0.0203(17) 0.038(2) -0.0093(15) 0.0058(15) -0.0073(15) O33 0.030(2) 0.0283(19) 0.040(2) 0.0061(15) 0.0055(15) -0.0089(16) O37A 0.045(2) 0.0299(19) 0.0305(19) -0.0068(15) 0.0042(16) -0.0140(17) O37B 0.037(2) 0.0275(19) 0.0337(19) 0.0015(15) -0.0021(15) -0.0126(16) C31 0.012(2) 0.025(2) 0.028(2) -0.0005(19) -0.0055(19) -0.005(2) C32 0.014(2) 0.015(2) 0.033(3) -0.0074(19) -0.001(2) 0.0018(19) C33 0.020(3) 0.018(2) 0.023(2) 0.0018(18) -0.0026(19) -0.004(2) C34 0.022(3) 0.031(3) 0.026(3) -0.002(2) -0.002(2) -0.008(2) C35 0.022(3) 0.021(2) 0.035(3) -0.006(2) -0.003(2) -0.004(2) C36 0.021(3) 0.019(2) 0.030(3) -0.0012(19) -0.003(2) -0.006(2) C37 0.022(3) 0.017(2) 0.038(3) -0.007(2) -0.003(2) -0.007(2) N51 0.023(2) 0.0115(19) 0.028(2) -0.0028(15) -0.0025(16) -0.0064(17) N52 0.014(2) 0.0118(18) 0.028(2) -0.0028(15) -0.0028(16) -0.0036(16) N53 0.032(2) 0.0148(19) 0.026(2) -0.0008(16) -0.0040(17) -0.0140(18) N54 0.019(2) 0.0143(19) 0.023(2) -0.0029(15) -0.0014(16) -0.0079(16) N55 0.029(2) 0.016(2) 0.029(2) -0.0060(16) 0.0022(17) -0.0114(17) N56 0.023(2) 0.0134(19) 0.025(2) -0.0071(15) 0.0016(16) -0.0088(16) C51 0.007(2) 0.011(2) 0.034(3) -0.0039(18) -0.0041(19) -0.0023(18) C53 0.014(2) 0.013(2) 0.027(2) -0.0003(18) -0.0060(19) -0.0032(19) C55 0.011(2) 0.007(2) 0.034(3) -0.0023(18) -0.0054(19) -0.0040(18) N61 0.022(2) 0.0128(19) 0.024(2) -0.0038(15) 0.0031(16) -0.0055(16) N62 0.0119(19) 0.0138(19) 0.026(2) -0.0015(15) -0.0023(15) -0.0042(15) N63 0.029(2) 0.016(2) 0.028(2) -0.0039(16) 0.0004(17) -0.0141(18) N64 0.016(2) 0.0134(19) 0.026(2) -0.0037(15) 0.0001(16) -0.0060(16) N65 0.025(2) 0.0122(19) 0.028(2) -0.0016(16) 0.0039(16) -0.0083(17) N66 0.021(2) 0.0125(18) 0.0207(19) -0.0024(15) 0.0002(15) -0.0085(16) C61 0.010(2) 0.012(2) 0.029(3) -0.0006(18) -0.0055(19) -0.0042(18) C63 0.013(2) 0.010(2) 0.025(2) 0.0015(17) -0.0046(18) -0.0021(18) C65 0.011(2) 0.012(2) 0.029(3) -0.0009(18) -0.0011(19) -0.0039(19) N41 0.024(2) 0.0134(19) 0.036(2) -0.0053(16) 0.0006(17) -0.0064(17) N42 0.023(2) 0.0134(19) 0.026(2) -0.0036(15) 0.0000(16) -0.0078(17) N43 0.021(2) 0.0129(19) 0.031(2) -0.0078(16) 0.0026(16) -0.0067(16) N44 0.0136(19) 0.0115(18) 0.029(2) -0.0046(15) -0.0022(16) -0.0044(15) N45 0.039(2) 0.0147(19) 0.024(2) -0.0046(16) 0.0010(18) -0.0171(18) N46 0.020(2) 0.0116(19) 0.029(2) -0.0039(15) -0.0028(16) -0.0051(16) C41 0.010(2) 0.013(2) 0.035(3) -0.0052(19) -0.0043(19) -0.0019(19) C43 0.010(2) 0.010(2) 0.033(3) -0.0043(18) -0.0042(19) -0.0035(18) C45 0.009(2) 0.006(2) 0.037(3) -0.0025(18) -0.0064(19) 0.0009(18) O12 0.038(2) 0.0262(19) 0.0314(19) -0.0027(15) 0.0004(15) -0.0119(16) O13 0.032(2) 0.0285(19) 0.036(2) -0.0045(15) -0.0023(15) -0.0078(16) O17A 0.047(2) 0.029(2) 0.034(2) -0.0049(16) 0.0035(16) -0.0159(18) O17B 0.036(2) 0.0236(18) 0.036(2) -0.0090(15) 0.0011(16) -0.0107(16) C11 0.018(3) 0.025(2) 0.030(2) -0.0021(19) -0.0051(19) -0.011(2) C12 0.020(3) 0.020(2) 0.030(2) 0.0027(19) -0.008(2) -0.010(2) C13 0.018(3) 0.018(2) 0.039(3) -0.002(2) -0.004(2) -0.008(2) C14 0.025(3) 0.039(3) 0.021(2) -0.003(2) -0.002(2) -0.013(2) C15 0.026(3) 0.023(3) 0.036(3) -0.003(2) 0.000(2) -0.012(2) C16 0.019(3) 0.016(2) 0.041(3) 0.001(2) -0.008(2) -0.008(2) C17 0.021(3) 0.025(3) 0.040(3) -0.005(2) -0.006(2) -0.010(2) O94 0.041(2) 0.0242(18) 0.0298(19) -0.0072(14) 0.0019(15) -0.0136(16) O95 0.034(2) 0.035(2) 0.045(2) -0.0057(17) -0.0033(17) -0.0048(17) O97 0.048(2) 0.033(2) 0.035(2) -0.0031(16) 0.0021(16) -0.0182(18) O96 0.046(2) 0.027(2) 0.049(2) -0.0051(17) -0.0024(18) -0.0126(18) O99 0.037(2) 0.041(2) 0.053(2) -0.0063(18) -0.0047(18) -0.0097(18) O92 0.033(2) 0.0240(18) 0.044(2) 0.0009(15) -0.0016(16) -0.0116(16) O91 0.044(2) 0.033(2) 0.039(2) 0.0043(16) -0.0049(16) -0.0213(18) O90 0.069(3) 0.042(2) 0.034(2) -0.0064(17) 0.0016(18) -0.034(2) O100 0.056(3) 0.042(2) 0.040(2) -0.0087(17) -0.0107(18) -0.020(2) O93 0.032(2) 0.0253(19) 0.041(2) -0.0016(15) -0.0044(16) -0.0113(16) O98 0.034(2) 0.0304(19) 0.036(2) -0.0062(15) 0.0008(15) -0.0106(16) _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 O22 C22 1.369(5) . ? O23 C23 1.368(5) . ? O27A C27 1.277(5) . ? O27B C27 1.271(5) . ? C21 C22 1.384(6) . ? C21 C26 1.413(6) . ? C21 C27 1.483(6) . ? C22 C23 1.395(6) . ? C23 C24 1.381(6) . ? C24 C25 1.401(6) . ? C25 C26 1.366(6) . ? O32 C32 1.356(5) . ? O33 C33 1.381(5) . ? O37A C37 1.271(5) . ? O37B C37 1.267(5) . ? C31 C36 1.406(6) . ? C31 C32 1.413(6) . ? C31 C37 1.483(6) . ? C32 C33 1.375(6) . ? C33 C34 1.381(6) . ? C34 C35 1.391(6) . ? C35 C36 1.344(6) . ? N51 C51 1.329(5) . ? N52 C51 1.318(5) . ? N52 C53 1.350(5) . ? N53 C53 1.324(5) . ? N54 C55 1.315(5) . ? N54 C53 1.365(5) . ? N55 C55 1.325(5) . ? N56 C55 1.368(5) . ? N56 C51 1.373(5) . ? N61 C61 1.326(5) . ? N62 C61 1.313(5) . ? N62 C63 1.368(5) . ? N63 C63 1.318(5) . ? N64 C65 1.330(5) . ? N64 C63 1.352(5) . ? N65 C65 1.315(5) . ? N66 C61 1.362(5) . ? N66 C65 1.366(5) . ? N41 C41 1.335(5) . ? N42 C41 1.366(5) . ? N42 C43 1.368(5) . ? N43 C43 1.319(5) . ? N44 C43 1.317(5) . ? N44 C45 1.364(5) . ? N45 C45 1.312(5) . ? N46 C41 1.303(5) . ? N46 C45 1.358(5) . ? O12 C12 1.364(5) . ? O13 C13 1.388(5) . ? O17A C17 1.279(5) . ? O17B C17 1.275(5) . ? C11 C16 1.393(6) . ? C11 C12 1.393(6) . ? C11 C17 1.489(6) . ? C12 C13 1.377(6) . ? C13 C14 1.367(6) . ? C14 C15 1.408(6) . ? C15 C16 1.364(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C22 C21 C26 119.4(4) . . ? C22 C21 C27 120.7(4) . . ? C26 C21 C27 119.9(4) . . ? O22 C22 C21 123.2(4) . . ? O22 C22 C23 116.7(4) . . ? C21 C22 C23 120.1(4) . . ? O23 C23 C24 123.5(4) . . ? O23 C23 C22 116.6(4) . . ? C24 C23 C22 119.9(4) . . ? C23 C24 C25 120.5(4) . . ? C26 C25 C24 119.6(4) . . ? C25 C26 C21 120.5(4) . . ? O27B C27 O27A 121.1(4) . . ? O27B C27 C21 119.9(4) . . ? O27A C27 C21 118.9(4) . . ? C36 C31 C32 118.4(4) . . ? C36 C31 C37 119.9(4) . . ? C32 C31 C37 121.7(4) . . ? O32 C32 C33 118.5(4) . . ? O32 C32 C31 121.8(4) . . ? C33 C32 C31 119.7(4) . . ? C32 C33 C34 120.4(4) . . ? C32 C33 O33 118.7(4) . . ? C34 C33 O33 120.9(4) . . ? C33 C34 C35 120.0(4) . . ? C36 C35 C34 120.5(4) . . ? C35 C36 C31 120.9(4) . . ? O37B C37 O37A 121.5(4) . . ? O37B C37 C31 119.8(4) . . ? O37A C37 C31 118.7(4) . . ? C51 N52 C53 116.2(4) . . ? C55 N54 C53 115.9(3) . . ? C55 N56 C51 118.3(4) . . ? N52 C51 N51 121.0(4) . . ? N52 C51 N56 122.0(4) . . ? N51 C51 N56 117.0(4) . . ? N53 C53 N52 117.4(4) . . ? N53 C53 N54 117.2(4) . . ? N52 C53 N54 125.3(4) . . ? N54 C55 N55 121.4(4) . . ? N54 C55 N56 122.2(4) . . ? N55 C55 N56 116.4(4) . . ? C61 N62 C63 115.7(4) . . ? C65 N64 C63 116.3(3) . . ? C61 N66 C65 118.6(4) . . ? N62 C61 N61 120.7(4) . . ? N62 C61 N66 122.8(4) . . ? N61 C61 N66 116.4(4) . . ? N63 C63 N64 118.7(4) . . ? N63 C63 N62 116.2(4) . . ? N64 C63 N62 125.1(4) . . ? N65 C65 N64 121.3(4) . . ? N65 C65 N66 117.1(4) . . ? N64 C65 N66 121.5(4) . . ? C41 N42 C43 118.3(4) . . ? C43 N44 C45 116.0(4) . . ? C41 N46 C45 115.7(4) . . ? N46 C41 N41 120.9(4) . . ? N46 C41 N42 122.9(4) . . ? N41 C41 N42 116.2(4) . . ? N44 C43 N43 121.4(4) . . ? N44 C43 N42 121.8(4) . . ? N43 C43 N42 116.9(4) . . ? N45 C45 N46 117.9(4) . . ? N45 C45 N44 116.9(4) . . ? N46 C45 N44 125.2(4) . . ? C16 C11 C12 118.5(4) . . ? C16 C11 C17 121.3(4) . . ? C12 C11 C17 120.2(4) . . ? O12 C12 C13 117.6(4) . . ? O12 C12 C11 122.1(4) . . ? C13 C12 C11 120.3(4) . . ? C14 C13 C12 120.6(4) . . ? C14 C13 O13 121.0(4) . . ? C12 C13 O13 118.4(4) . . ? C13 C14 C15 120.1(4) . . ? C16 C15 C14 118.9(4) . . ? C15 C16 C11 121.7(4) . . ? O17B C17 O17A 122.3(4) . . ? O17B C17 C11 120.5(4) . . ? O17A C17 C11 117.2(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.536 _refine_diff_density_min -0.364 _refine_diff_density_rms 0.089 # Attachment '24DHB.CIF' data_2 _database_code_depnum_ccdc_archive 'CCDC 782609' #TrackingRef '24DHB.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H5 O4, C3 H7 N6, 2(H2 O)' _chemical_formula_sum 'C10 H16 N6 O6' _chemical_formula_weight 316.29 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.7880(10) _cell_length_b 12.1600(10) _cell_length_c 7.1610 _cell_angle_alpha 90.000 _cell_angle_beta 96.560(5) _cell_angle_gamma 90.000 _cell_volume 1365.78(14) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3231 _cell_measurement_theta_min 2.5925 _cell_measurement_theta_max 29.1747 _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9823 _exptl_absorpt_correction_T_max 0.9898 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13382 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_sigmaI/netI 0.0558 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.10 _reflns_number_total 2437 _reflns_number_gt 1363 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlisPro RED (Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXTL (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1997)' _computing_molecular_graphics 'XP Suite SHELXTL' _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^)+(0.1030P)^2^+0.7691P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef ? _refine_ls_number_reflns 2437 _refine_ls_number_parameters 223 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1108 _refine_ls_R_factor_gt 0.0659 _refine_ls_wR_factor_ref 0.1773 _refine_ls_wR_factor_gt 0.1608 _refine_ls_goodness_of_fit_ref 0.900 _refine_ls_restrained_S_all 0.900 _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 N21 N 0.09204(17) 0.4346(2) 0.4135(4) 0.0329(8) Uani 1 1 d . . . H21A H 0.0707 0.4975 0.3797 0.039 Uiso 1 1 calc R . . H21B H 0.1417 0.4308 0.4765 0.039 Uiso 1 1 calc R . . N22 N 0.08613(18) 0.2468(2) 0.4268(4) 0.0242(7) Uani 1 1 d . . . N23 N 0.08738(17) 0.0589(2) 0.4183(4) 0.0294(7) Uani 1 1 d . . . H23B H 0.0642 -0.0033 0.3864 0.035 Uiso 1 1 calc R . . H23A H 0.1371 0.0610 0.4812 0.035 Uiso 1 1 calc R . . N24 N -0.02979(16) 0.1492(2) 0.2744(4) 0.0230(7) Uani 1 1 d . . . N25 N -0.14406(17) 0.2501(2) 0.1476(4) 0.0310(7) Uani 1 1 d . . . H25A H -0.1703 0.1893 0.1193 0.037 Uiso 1 1 calc R . . H25B H -0.1689 0.3118 0.1195 0.037 Uiso 1 1 calc R . . N26 N -0.02788(16) 0.3475(2) 0.2716(4) 0.0234(7) Uani 1 1 d . . . C21 C 0.0486(2) 0.3437(2) 0.3685(5) 0.0223(8) Uani 1 1 d . . . C23 C 0.04676(19) 0.1510(2) 0.3711(4) 0.0202(7) Uani 1 1 d . . . C25 C -0.06573(19) 0.2487(2) 0.2338(4) 0.0219(7) Uani 1 1 d . . . H22 H 0.135(3) 0.245(3) 0.491(6) 0.064(14) Uiso 1 1 d . . . O12 O 0.36487(15) 0.39616(18) 0.2417(4) 0.0449(8) Uani 1 1 d . . . H12 H 0.3162 0.3814 0.1963 0.067 Uiso 1 1 calc R . . O14 O 0.62922(17) 0.2241(2) 0.4488(5) 0.0523(9) Uani 1 1 d . . . O17A O 0.24008(15) 0.2722(2) 0.1179(4) 0.0409(7) Uani 1 1 d . . . O17B O 0.25027(16) 0.0914(2) 0.1447(4) 0.0461(8) Uani 1 1 d . . . C11 C 0.3739(2) 0.1984(3) 0.2406(5) 0.0287(8) Uani 1 1 d . . . C12 C 0.4097(2) 0.3025(3) 0.2742(5) 0.0313(9) Uani 1 1 d . . . C13 C 0.4957(2) 0.3123(3) 0.3469(5) 0.0356(9) Uani 1 1 d . . . H13 H 0.5195 0.3814 0.3722 0.043 Uiso 1 1 calc R . . C14 C 0.5442(2) 0.2203(3) 0.3804(5) 0.0337(9) Uani 1 1 d . . . C15 C 0.5097(2) 0.1161(3) 0.3449(5) 0.0386(10) Uani 1 1 d . . . H15 H 0.5432 0.0535 0.3673 0.046 Uiso 1 1 calc R . . C16 C 0.4251(2) 0.1076(3) 0.2761(5) 0.0386(10) Uani 1 1 d . . . H16 H 0.4017 0.0381 0.2528 0.046 Uiso 1 1 calc R . . C17 C 0.2827(2) 0.1872(3) 0.1633(5) 0.0345(9) Uani 1 1 d . . . H14 H 0.641(2) 0.287(2) 0.477(4) 0.010(9) Uiso 1 1 d . . . O90 O -0.2931(2) 0.0860(3) 0.0653(5) 0.0593(9) Uani 1 1 d D . . H90A H -0.263(2) 0.037(2) 0.036(5) 0.036(12) Uiso 1 1 d D . . H90B H -0.317(3) 0.052(4) 0.142(6) 0.09(2) Uiso 1 1 d D . . O91 O -0.2510(2) 0.4443(3) 0.0501(5) 0.0548(9) Uani 1 1 d . . . H91B H -0.294(2) 0.405(2) 0.049(4) 0.007(8) Uiso 1 1 d . . . H914 H -0.260(3) 0.484(4) 0.150(7) 0.09(2) 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 N21 0.0253(15) 0.0181(14) 0.051(2) 0.0005(14) -0.0141(14) -0.0038(12) N22 0.0197(15) 0.0210(14) 0.0300(17) 0.0025(13) -0.0044(12) -0.0001(12) N23 0.0232(15) 0.0167(14) 0.046(2) 0.0014(13) -0.0074(13) 0.0014(12) N24 0.0209(15) 0.0159(13) 0.0313(17) 0.0003(12) -0.0010(13) 0.0015(11) N25 0.0231(15) 0.0190(14) 0.0471(19) 0.0002(14) -0.0120(13) 0.0006(12) N26 0.0209(15) 0.0165(14) 0.0313(17) 0.0005(12) -0.0025(13) -0.0014(11) C21 0.0229(18) 0.0190(16) 0.024(2) 0.0021(14) -0.0010(15) 0.0010(13) C23 0.0189(17) 0.0180(16) 0.0235(19) 0.0005(14) 0.0015(14) -0.0002(13) C25 0.0229(17) 0.0227(16) 0.0198(17) -0.0021(15) 0.0013(14) 0.0000(14) O12 0.0321(15) 0.0286(14) 0.071(2) -0.0012(13) -0.0075(14) 0.0030(11) O14 0.0224(15) 0.0467(19) 0.084(2) 0.0064(17) -0.0120(14) 0.0010(13) O17A 0.0258(14) 0.0412(15) 0.0524(18) 0.0046(13) -0.0101(12) 0.0083(11) O17B 0.0320(15) 0.0362(15) 0.067(2) 0.0018(14) -0.0079(13) -0.0066(12) C11 0.032(2) 0.0239(18) 0.030(2) 0.0005(16) 0.0030(16) -0.0010(15) C12 0.033(2) 0.0302(19) 0.031(2) 0.0023(17) 0.0036(16) 0.0098(16) C13 0.032(2) 0.035(2) 0.038(2) 0.0028(18) -0.0006(17) -0.0045(16) C14 0.0208(18) 0.043(2) 0.036(2) 0.0037(17) -0.0033(16) 0.0039(16) C15 0.029(2) 0.037(2) 0.048(3) 0.0030(19) -0.0019(18) 0.0054(17) C16 0.041(2) 0.0280(19) 0.046(3) 0.0009(18) 0.0018(19) -0.0008(17) C17 0.031(2) 0.035(2) 0.037(2) -0.0047(18) 0.0003(17) -0.0036(17) O90 0.063(2) 0.0392(18) 0.077(3) 0.0061(18) 0.0150(19) -0.0007(17) O91 0.0371(18) 0.0425(17) 0.083(3) -0.0100(18) -0.0005(16) 0.0019(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 N21 C21 1.320(4) . ? N21 H21A 0.8600 . ? N21 H21B 0.8600 . ? N22 C23 1.359(4) . ? N22 C21 1.362(4) . ? N22 H22 0.85(5) . ? N23 C23 1.315(4) . ? N23 H23B 0.8600 . ? N23 H23A 0.8600 . ? N24 C23 1.323(4) . ? N24 C25 1.354(4) . ? N25 C25 1.318(4) . ? N25 H25A 0.8600 . ? N25 H25B 0.8600 . ? N26 C21 1.324(4) . ? N26 C25 1.356(4) . ? O12 C12 1.347(4) . ? O12 H12 0.8200 . ? O14 C14 1.376(4) . ? O14 H14 0.81(3) . ? O17A C17 1.256(4) . ? O17B C17 1.273(4) . ? C11 C16 1.375(5) . ? C11 C12 1.396(5) . ? C11 C17 1.489(5) . ? C12 C13 1.403(5) . ? C13 C14 1.361(5) . ? C13 H13 0.9300 . ? C14 C15 1.392(5) . ? C15 C16 1.373(5) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? O90 H90A 0.800(18) . ? O90 H90B 0.814(19) . ? O91 H91B 0.83(3) . ? O91 H914 0.89(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C21 N21 H21A 120.0 . . ? C21 N21 H21B 120.0 . . ? H21A N21 H21B 120.0 . . ? C23 N22 C21 118.9(3) . . ? C23 N22 H22 120(3) . . ? C21 N22 H22 121(3) . . ? C23 N23 H23B 120.0 . . ? C23 N23 H23A 120.0 . . ? H23B N23 H23A 120.0 . . ? C23 N24 C25 115.7(3) . . ? C25 N25 H25A 120.0 . . ? C25 N25 H25B 120.0 . . ? H25A N25 H25B 120.0 . . ? C21 N26 C25 115.4(3) . . ? N21 C21 N26 121.0(3) . . ? N21 C21 N22 117.0(3) . . ? N26 C21 N22 122.0(3) . . ? N23 C23 N24 120.7(3) . . ? N23 C23 N22 117.5(3) . . ? N24 C23 N22 121.8(3) . . ? N25 C25 N24 117.4(3) . . ? N25 C25 N26 116.8(3) . . ? N24 C25 N26 125.8(3) . . ? C12 O12 H12 109.5 . . ? C14 O14 H14 108(2) . . ? C16 C11 C12 118.6(3) . . ? C16 C11 C17 121.2(3) . . ? C12 C11 C17 120.2(3) . . ? O12 C12 C11 122.9(3) . . ? O12 C12 C13 117.3(3) . . ? C11 C12 C13 119.8(3) . . ? C14 C13 C12 119.8(3) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 O14 122.8(3) . . ? C13 C14 C15 121.1(3) . . ? O14 C14 C15 116.2(3) . . ? C16 C15 C14 118.5(3) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C15 C16 C11 122.3(3) . . ? C15 C16 H16 118.9 . . ? C11 C16 H16 118.9 . . ? O17A C17 O17B 122.0(3) . . ? O17A C17 C11 119.1(3) . . ? O17B C17 C11 118.9(3) . . ? H90A O90 H90B 97(4) . . ? H91B O91 H914 97(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C25 N26 C21 N21 179.8(3) . . . . ? C25 N26 C21 N22 -0.4(5) . . . . ? C23 N22 C21 N21 -174.9(3) . . . . ? C23 N22 C21 N26 5.3(5) . . . . ? C25 N24 C23 N23 179.9(3) . . . . ? C25 N24 C23 N22 0.4(5) . . . . ? C21 N22 C23 N23 175.2(3) . . . . ? C21 N22 C23 N24 -5.3(5) . . . . ? C23 N24 C25 N25 -176.0(3) . . . . ? C23 N24 C25 N26 5.0(5) . . . . ? C21 N26 C25 N25 176.0(3) . . . . ? C21 N26 C25 N24 -5.0(5) . . . . ? C16 C11 C12 O12 179.2(3) . . . . ? C17 C11 C12 O12 0.8(5) . . . . ? C16 C11 C12 C13 -1.5(5) . . . . ? C17 C11 C12 C13 -179.9(3) . . . . ? O12 C12 C13 C14 -179.3(3) . . . . ? C11 C12 C13 C14 1.5(5) . . . . ? C12 C13 C14 O14 179.0(4) . . . . ? C12 C13 C14 C15 -0.5(6) . . . . ? C13 C14 C15 C16 -0.4(6) . . . . ? O14 C14 C15 C16 -179.9(3) . . . . ? C14 C15 C16 C11 0.3(6) . . . . ? C12 C11 C16 C15 0.6(6) . . . . ? C17 C11 C16 C15 179.0(4) . . . . ? C16 C11 C17 O17A -174.0(3) . . . . ? C12 C11 C17 O17A 4.4(5) . . . . ? C16 C11 C17 O17B 5.9(5) . . . . ? C12 C11 C17 O17B -175.8(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.818 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.079 # Attachment '25DHB.CIF' data_3 _database_code_depnum_ccdc_archive 'CCDC 782610' #TrackingRef '25DHB.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; 2(C7 H6 O4), 2(C3 H6 N6), 2(C3 H7 N O), 2(H2 O) ; _chemical_formula_sum 'C26 H36 N14 O12' _chemical_formula_weight 736.69 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 'C 2/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 38.011(5) _cell_length_b 9.212(5) _cell_length_c 20.430(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 99.437(5) _cell_angle_gamma 90.000(5) _cell_volume 7057(4) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 8448 _cell_measurement_theta_min 2.4426 _cell_measurement_theta_max 29.3352 _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3088 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9813 _exptl_absorpt_correction_T_max 0.9900 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)' _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 'Oxford Xcalibur,Eos(Nova) CCD detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34754 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_sigmaI/netI 0.0647 _diffrn_reflns_limit_h_min -45 _diffrn_reflns_limit_h_max 45 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.24 _reflns_number_total 6376 _reflns_number_gt 3172 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlisPro RED (Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXTL (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1997)' _computing_molecular_graphics 'XP Suite SHELXTL' _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^)+(0.1652P)^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 SHELXL _refine_ls_extinction_coef ? _refine_ls_number_reflns 6376 _refine_ls_number_parameters 469 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1367 _refine_ls_R_factor_gt 0.0784 _refine_ls_wR_factor_ref 0.2652 _refine_ls_wR_factor_gt 0.2389 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_restrained_S_all 0.972 _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 O12 O 0.26117(7) 0.3030(3) 0.22524(13) 0.0469(7) Uani 1 1 d . . . H12 H 0.2602 0.2589 0.1901 0.070 Uiso 1 1 calc R . . O15 O 0.37243(8) 0.6948(3) 0.26013(16) 0.0600(9) Uani 1 1 d . . . H15 H 0.3724 0.7413 0.2944 0.090 Uiso 1 1 calc R . . O17A O 0.27935(8) 0.2339(3) 0.11702(13) 0.0508(8) Uani 1 1 d . . . H17A H 0.2784 0.1886 0.0822 0.076 Uiso 1 1 calc R . . O17B O 0.32711(8) 0.3260(3) 0.08419(14) 0.0572(8) Uani 1 1 d . . . C11 C 0.31176(10) 0.4098(4) 0.18566(18) 0.0352(9) Uani 1 1 d . . . C12 C 0.28886(10) 0.3984(4) 0.23220(18) 0.0347(9) Uani 1 1 d . . . C13 C 0.29364(11) 0.4877(4) 0.28787(19) 0.0447(11) Uani 1 1 d . . . H13 H 0.2781 0.4816 0.3185 0.054 Uiso 1 1 calc R . . C14 C 0.32166(11) 0.5859(4) 0.2975(2) 0.0461(11) Uani 1 1 d . . . H14 H 0.3249 0.6450 0.3349 0.055 Uiso 1 1 calc R . . C15 C 0.34480(11) 0.5969(4) 0.2524(2) 0.0449(10) Uani 1 1 d . . . C16 C 0.30620(11) 0.3185(4) 0.12431(18) 0.0369(9) Uani 1 1 d . . . C38 C 0.33934(10) 0.5104(4) 0.19622(19) 0.0404(10) Uani 1 1 d . . . H38A H 0.3544 0.5198 0.1650 0.048 Uiso 1 1 calc R . . O22 O 0.33781(7) 0.3119(3) 0.43080(13) 0.0505(8) Uani 1 1 d . . . H22 H 0.3378 0.2622 0.3975 0.076 Uiso 1 1 calc R . . O25 O 0.45595(9) 0.6659(4) 0.48410(19) 0.0863(12) Uani 1 1 d . . . H25 H 0.4684 0.6622 0.4550 0.129 Uiso 1 1 calc R . . O27A O 0.36137(8) 0.2189(3) 0.33000(13) 0.0513(8) Uani 1 1 d . . . H27A H 0.3615 0.1684 0.2970 0.077 Uiso 1 1 calc R . . O27B O 0.41303(8) 0.2916(3) 0.30458(14) 0.0575(8) Uani 1 1 d . . . C21 C 0.39293(10) 0.3943(4) 0.39916(19) 0.0400(10) Uani 1 1 d . . . C22 C 0.36760(10) 0.3974(4) 0.44081(19) 0.0398(10) Uani 1 1 d . . . C23 C 0.37177(12) 0.4899(5) 0.4949(2) 0.0483(11) Uani 1 1 d . . . H23 H 0.3547 0.4921 0.5227 0.058 Uiso 1 1 calc R . . C24 C 0.40108(13) 0.5784(5) 0.5074(2) 0.0595(13) Uani 1 1 d . . . H24 H 0.4035 0.6410 0.5436 0.071 Uiso 1 1 calc R . . C25 C 0.42701(12) 0.5768(5) 0.4677(2) 0.0568(12) Uani 1 1 d . . . C26 C 0.42293(12) 0.4843(5) 0.4133(2) 0.0533(12) Uani 1 1 d . . . H26 H 0.4403 0.4820 0.3860 0.064 Uiso 1 1 calc R . . C27 C 0.38923(12) 0.2960(5) 0.3398(2) 0.0442(10) Uani 1 1 d . . . N31 N 0.39973(9) 0.1415(4) 0.17912(18) 0.0546(10) Uani 1 1 d . . . H31A H 0.4133 0.1451 0.1494 0.066 Uiso 1 1 calc R . . H31B H 0.4047 0.1928 0.2146 0.066 Uiso 1 1 calc R . . N32 N 0.35132(8) 0.0550(3) 0.22020(15) 0.0390(8) Uani 1 1 d . . . N33 N 0.30449(9) -0.0359(4) 0.26435(15) 0.0455(9) Uani 1 1 d . . . H33B H 0.2860 -0.0906 0.2626 0.055 Uiso 1 1 calc R . . H33A H 0.3114 0.0165 0.2989 0.055 Uiso 1 1 calc R . . N34 N 0.31188(8) -0.1128(3) 0.16057(15) 0.0381(8) Uani 1 1 d . . . N35 N 0.32410(9) -0.1894(4) 0.06127(16) 0.0469(9) Uani 1 1 d . . . H35B H 0.3055 -0.2436 0.0580 0.056 Uiso 1 1 calc R . . H5B H 0.3369 -0.1891 0.0302 0.056 Uiso 1 1 calc R . . N36 N 0.36270(9) -0.0240(4) 0.11582(16) 0.0463(9) Uani 1 1 d . . . C31 C 0.37137(11) 0.0576(4) 0.17035(19) 0.0406(10) Uani 1 1 d . . . C33 C 0.32217(10) -0.0324(4) 0.21434(18) 0.0340(9) Uani 1 1 d . . . C35 C 0.33317(10) -0.1059(4) 0.11444(18) 0.0366(9) Uani 1 1 d . . . N41 N 0.27246(9) 0.5046(4) -0.04862(15) 0.0463(9) Uani 1 1 d . . . H41B H 0.2902 0.5623 -0.0491 0.056 Uiso 1 1 calc R . . H41A H 0.2667 0.4432 -0.0803 0.056 Uiso 1 1 calc R . . N42 N 0.26194(8) 0.6031(3) 0.05020(15) 0.0352(8) Uani 1 1 d . . . N43 N 0.24844(9) 0.6882(3) 0.14728(15) 0.0434(8) Uani 1 1 d . . . H43B H 0.2357 0.6900 0.1784 0.052 Uiso 1 1 calc R . . H43A H 0.2665 0.7453 0.1489 0.052 Uiso 1 1 calc R . . N44 N 0.21176(8) 0.5098(3) 0.09647(14) 0.0375(8) Uani 1 1 d . . . N45 N 0.17856(9) 0.3264(4) 0.03986(16) 0.0505(9) Uani 1 1 d . . . H45A H 0.1648 0.3244 0.0693 0.061 Uiso 1 1 calc R . . H45B H 0.1748 0.2680 0.0066 0.061 Uiso 1 1 calc R . . N46 N 0.22612(8) 0.4139(3) -0.00260(14) 0.0372(8) Uani 1 1 d . . . C41 C 0.25389(10) 0.5104(4) 0.00098(18) 0.0352(9) Uani 1 1 d . . . C43 C 0.24033(10) 0.5974(4) 0.09687(17) 0.0332(9) Uani 1 1 d . . . C45 C 0.20553(10) 0.4192(4) 0.04572(18) 0.0364(9) Uani 1 1 d . . . O51 O 0.4992(2) 0.6748(14) 0.0995(5) 0.248(5) Uani 1 1 d . . . N24 N 0.45654(14) 0.6576(8) 0.1563(3) 0.115(2) Uani 1 1 d . . . C51 C 0.4815(3) 0.6222(14) 0.1204(4) 0.158(4) Uani 1 1 d . . . C52 C 0.4372(5) 0.7875(14) 0.1582(9) 0.369(14) Uani 1 1 d . . . H52B H 0.4473 0.8613 0.1337 0.553 Uiso 1 1 calc R . . H52A H 0.4384 0.8180 0.2034 0.553 Uiso 1 1 calc R . . H21C H 0.4128 0.7716 0.1387 0.553 Uiso 1 1 calc R . . C53 C 0.4435(2) 0.5411(10) 0.1950(6) 0.178(4) Uani 1 1 d . . . H53A H 0.4566 0.4537 0.1905 0.267 Uiso 1 1 calc R . . H53B H 0.4186 0.5246 0.1790 0.267 Uiso 1 1 calc R . . H20C H 0.4466 0.5688 0.2409 0.267 Uiso 1 1 calc R . . O61 O 0.37586(9) -0.1388(4) 0.37413(16) 0.0656(9) Uani 1 1 d . . . N83 N 0.42445(15) -0.0102(7) 0.4172(4) 0.115(2) Uani 1 1 d . . . C61 C 0.4161(6) -0.0754(12) 0.3700(10) 0.42(2) Uani 1 1 d . . . C62 C 0.45560(17) 0.0572(8) 0.4408(4) 0.125(3) Uani 1 1 d . . . C63 C 0.4010(3) -0.009(2) 0.4509(16) 0.53(3) Uani 1 1 d . . . O91 O 0.45878(9) 0.1600(4) 0.09915(18) 0.0816(11) Uani 1 1 d . . . O90 O 0.48564(11) 0.2859(7) 0.3098(3) 0.153(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 O12 0.0569(18) 0.0545(18) 0.0330(15) -0.0050(13) 0.0182(13) -0.0115(15) O15 0.0575(19) 0.064(2) 0.061(2) -0.0134(16) 0.0173(15) -0.0155(17) O17A 0.0612(19) 0.0606(19) 0.0333(16) -0.0160(13) 0.0154(14) -0.0072(16) O17B 0.070(2) 0.067(2) 0.0414(17) -0.0107(15) 0.0294(16) -0.0044(16) C11 0.043(2) 0.035(2) 0.027(2) 0.0053(16) 0.0075(17) 0.0090(19) C12 0.042(2) 0.035(2) 0.029(2) 0.0044(17) 0.0108(18) 0.0031(19) C13 0.058(3) 0.052(3) 0.027(2) -0.0036(19) 0.0177(19) 0.004(2) C14 0.058(3) 0.048(3) 0.033(2) -0.0060(19) 0.012(2) -0.001(2) C15 0.046(2) 0.045(2) 0.044(3) 0.000(2) 0.009(2) 0.000(2) C16 0.045(2) 0.040(2) 0.027(2) 0.0029(17) 0.0103(18) 0.005(2) C38 0.043(2) 0.045(2) 0.036(2) -0.0001(18) 0.0179(19) -0.001(2) O22 0.0501(18) 0.0625(19) 0.0428(17) -0.0130(14) 0.0192(14) -0.0087(15) O25 0.077(2) 0.097(3) 0.091(3) -0.036(2) 0.031(2) -0.042(2) O27A 0.0559(19) 0.0585(19) 0.0419(17) -0.0157(14) 0.0155(14) -0.0027(16) O27B 0.0505(18) 0.079(2) 0.0479(18) -0.0189(16) 0.0230(15) -0.0013(16) C21 0.040(2) 0.047(2) 0.034(2) -0.0032(18) 0.0078(18) 0.004(2) C22 0.038(2) 0.050(2) 0.033(2) -0.0005(18) 0.0102(18) 0.000(2) C23 0.049(3) 0.060(3) 0.040(2) -0.011(2) 0.017(2) -0.004(2) C24 0.067(3) 0.066(3) 0.049(3) -0.021(2) 0.019(2) -0.008(3) C25 0.056(3) 0.061(3) 0.055(3) -0.013(2) 0.016(2) -0.011(2) C26 0.048(3) 0.071(3) 0.046(3) -0.007(2) 0.021(2) -0.001(2) C27 0.045(2) 0.053(3) 0.036(2) -0.002(2) 0.012(2) 0.005(2) N31 0.053(2) 0.067(2) 0.049(2) -0.0148(18) 0.0222(18) -0.018(2) N32 0.0382(19) 0.047(2) 0.0341(18) -0.0025(15) 0.0119(15) -0.0002(16) N33 0.046(2) 0.056(2) 0.0371(19) -0.0100(16) 0.0172(16) -0.0065(17) N34 0.0389(19) 0.046(2) 0.0301(18) -0.0047(15) 0.0085(15) 0.0013(16) N35 0.054(2) 0.057(2) 0.0341(19) -0.0139(16) 0.0187(16) -0.0083(18) N36 0.050(2) 0.055(2) 0.036(2) -0.0074(16) 0.0143(17) -0.0044(18) C31 0.045(2) 0.041(2) 0.037(2) -0.0012(19) 0.0113(19) 0.005(2) C33 0.035(2) 0.041(2) 0.027(2) -0.0006(17) 0.0084(17) 0.0064(19) C35 0.038(2) 0.041(2) 0.031(2) -0.0008(18) 0.0088(18) 0.0010(19) N41 0.049(2) 0.063(2) 0.0309(19) -0.0106(16) 0.0189(16) -0.0076(18) N42 0.0398(18) 0.0394(19) 0.0276(17) -0.0007(14) 0.0087(14) 0.0011(15) N43 0.053(2) 0.049(2) 0.0318(18) -0.0095(16) 0.0150(15) -0.0009(17) N44 0.0453(19) 0.045(2) 0.0247(17) 0.0010(15) 0.0135(14) 0.0012(17) N45 0.058(2) 0.059(2) 0.039(2) -0.0085(17) 0.0232(17) -0.013(2) N46 0.0447(19) 0.0430(19) 0.0265(17) 0.0015(14) 0.0137(15) 0.0019(16) C41 0.037(2) 0.041(2) 0.029(2) 0.0037(17) 0.0080(17) 0.0096(19) C43 0.038(2) 0.035(2) 0.027(2) 0.0033(17) 0.0084(17) 0.0096(19) C45 0.039(2) 0.042(2) 0.029(2) 0.0041(18) 0.0074(18) 0.0041(19) O51 0.167(7) 0.401(15) 0.207(9) -0.033(8) 0.125(7) 0.022(8) N24 0.096(4) 0.145(5) 0.119(5) 0.034(4) 0.067(4) 0.023(4) C51 0.136(8) 0.258(12) 0.092(6) 0.001(6) 0.057(6) -0.072(8) C52 0.53(3) 0.188(13) 0.48(3) 0.146(16) 0.35(3) 0.169(17) C53 0.155(8) 0.154(8) 0.251(12) 0.049(8) 0.108(8) 0.025(7) O61 0.059(2) 0.077(2) 0.062(2) -0.0090(17) 0.0133(17) -0.0054(18) N83 0.059(3) 0.103(4) 0.166(6) 0.047(4) -0.031(4) -0.021(3) C61 0.57(3) 0.069(6) 0.45(3) 0.004(10) -0.44(3) -0.012(12) C62 0.067(4) 0.147(6) 0.148(7) 0.022(5) -0.020(4) -0.040(4) C63 0.068(6) 0.41(3) 1.08(6) 0.58(4) 0.035(18) 0.014(11) O91 0.067(2) 0.110(3) 0.073(2) 0.018(2) 0.0254(19) 0.006(2) O90 0.069(3) 0.284(7) 0.104(4) 0.064(4) 0.014(3) -0.013(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O12 C12 1.361(4) . ? O12 H12 0.8200 . ? O15 C15 1.374(5) . ? O15 H15 0.8200 . ? O17A C16 1.273(5) . ? O17A H17A 0.8200 . ? O17B C16 1.234(4) . ? C11 C38 1.389(5) . ? C11 C12 1.394(5) . ? C11 C16 1.496(5) . ? C12 C13 1.391(5) . ? C13 C14 1.386(6) . ? C13 H13 0.9300 . ? C14 C15 1.379(5) . ? C14 H14 0.9300 . ? C15 C38 1.385(5) . ? C38 H38A 0.9300 . ? O22 C22 1.367(5) . ? O22 H22 0.8200 . ? O25 C25 1.370(5) . ? O25 H25 0.8200 . ? O27A C27 1.264(5) . ? O27A H27A 0.8200 . ? O27B C27 1.246(5) . ? C21 C22 1.386(5) . ? C21 C26 1.401(6) . ? C21 C27 1.501(5) . ? C22 C23 1.384(6) . ? C23 C24 1.370(6) . ? C23 H23 0.9300 . ? C24 C25 1.376(6) . ? C24 H24 0.9300 . ? C25 C26 1.389(6) . ? C26 H26 0.9300 . ? N31 C31 1.315(5) . ? N31 H31A 0.8600 . ? N31 H31B 0.8600 . ? N32 C33 1.359(5) . ? N32 C31 1.369(5) . ? N33 C33 1.312(4) . ? N33 H33B 0.8600 . ? N33 H33A 0.8600 . ? N34 C33 1.329(5) . ? N34 C35 1.341(5) . ? N35 C35 1.329(5) . ? N35 H35B 0.8600 . ? N35 H5B 0.8600 . ? N36 C31 1.339(5) . ? N36 C35 1.349(5) . ? N41 C41 1.328(5) . ? N41 H41B 0.8600 . ? N41 H41A 0.8600 . ? N42 C41 1.317(5) . ? N42 C43 1.358(4) . ? N43 C43 1.323(4) . ? N43 H43B 0.8600 . ? N43 H43A 0.8600 . ? N44 C45 1.322(5) . ? N44 C43 1.352(5) . ? N45 C45 1.325(5) . ? N45 H45A 0.8600 . ? N45 H45B 0.8600 . ? N46 C45 1.358(4) . ? N46 C41 1.373(5) . ? O51 C51 0.983(10) . ? N24 C51 1.331(11) . ? N24 C52 1.408(12) . ? N24 C53 1.468(10) . ? C52 H52B 0.9600 . ? C52 H52A 0.9600 . ? C52 H21C 0.9600 . ? C53 H53A 0.9600 . ? C53 H53B 0.9600 . ? C53 H20C 0.9600 . ? O61 C61 1.65(2) . ? N83 C61 1.135(15) . ? N83 C63 1.21(2) . ? N83 C62 1.353(8) . ? C61 C63 1.93(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 O12 H12 109.5 . . ? C15 O15 H15 109.5 . . ? C16 O17A H17A 109.5 . . ? C38 C11 C12 119.0(3) . . ? C38 C11 C16 120.3(3) . . ? C12 C11 C16 120.7(4) . . ? O12 C12 C13 117.5(3) . . ? O12 C12 C11 122.4(3) . . ? C13 C12 C11 120.0(4) . . ? C14 C13 C12 119.8(4) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C15 C14 C13 120.8(4) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? O15 C15 C14 122.1(4) . . ? O15 C15 C38 118.8(4) . . ? C14 C15 C38 119.1(4) . . ? O17B C16 O17A 123.3(4) . . ? O17B C16 C11 120.5(4) . . ? O17A C16 C11 116.3(3) . . ? C15 C38 C11 121.3(4) . . ? C15 C38 H38A 119.4 . . ? C11 C38 H38A 119.4 . . ? C22 O22 H22 109.5 . . ? C25 O25 H25 109.5 . . ? C27 O27A H27A 109.5 . . ? C22 C21 C26 119.0(4) . . ? C22 C21 C27 121.7(4) . . ? C26 C21 C27 119.2(4) . . ? O22 C22 C23 117.2(3) . . ? O22 C22 C21 122.6(3) . . ? C23 C22 C21 120.2(4) . . ? C24 C23 C22 119.9(4) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C23 C24 C25 121.5(4) . . ? C23 C24 H24 119.2 . . ? C25 C24 H24 119.2 . . ? O25 C25 C24 118.2(4) . . ? O25 C25 C26 122.9(4) . . ? C24 C25 C26 118.8(4) . . ? C25 C26 C21 120.5(4) . . ? C25 C26 H26 119.7 . . ? C21 C26 H26 119.7 . . ? O27B C27 O27A 124.0(4) . . ? O27B C27 C21 120.4(4) . . ? O27A C27 C21 115.6(3) . . ? C31 N31 H31A 120.0 . . ? C31 N31 H31B 120.0 . . ? H31A N31 H31B 120.0 . . ? C33 N32 C31 119.3(3) . . ? C33 N33 H33B 120.0 . . ? C33 N33 H33A 120.0 . . ? H33B N33 H33A 120.0 . . ? C33 N34 C35 115.1(3) . . ? C35 N35 H35B 120.0 . . ? C35 N35 H5B 120.0 . . ? H35B N35 H5B 120.0 . . ? C31 N36 C35 114.9(3) . . ? N31 C31 N36 121.8(4) . . ? N31 C31 N32 116.9(4) . . ? N36 C31 N32 121.2(4) . . ? N33 C33 N34 120.7(4) . . ? N33 C33 N32 117.4(3) . . ? N34 C33 N32 121.9(3) . . ? N35 C35 N34 116.2(3) . . ? N35 C35 N36 116.3(3) . . ? N34 C35 N36 127.5(4) . . ? C41 N41 H41B 120.0 . . ? C41 N41 H41A 120.0 . . ? H41B N41 H41A 120.0 . . ? C41 N42 C43 114.8(3) . . ? C43 N43 H43B 120.0 . . ? C43 N43 H43A 120.0 . . ? H43B N43 H43A 120.0 . . ? C45 N44 C43 115.0(3) . . ? C45 N45 H45A 120.0 . . ? C45 N45 H45B 120.0 . . ? H45A N45 H45B 120.0 . . ? C45 N46 C41 117.9(3) . . ? N42 C41 N41 121.5(4) . . ? N42 C41 N46 122.8(3) . . ? N41 C41 N46 115.7(3) . . ? N43 C43 N44 117.8(3) . . ? N43 C43 N42 115.6(3) . . ? N44 C43 N42 126.6(3) . . ? N44 C45 N45 121.0(3) . . ? N44 C45 N46 122.9(4) . . ? N45 C45 N46 116.1(3) . . ? C51 N24 C52 130.3(9) . . ? C51 N24 C53 116.9(8) . . ? C52 N24 C53 112.4(7) . . ? O51 C51 N24 136.0(15) . . ? N24 C52 H52B 109.5 . . ? N24 C52 H52A 109.5 . . ? H52B C52 H52A 109.5 . . ? N24 C52 H21C 109.5 . . ? H52B C52 H21C 109.5 . . ? H52A C52 H21C 109.5 . . ? N24 C53 H53A 109.5 . . ? N24 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? N24 C53 H20C 109.5 . . ? H53A C53 H20C 109.5 . . ? H53B C53 H20C 109.5 . . ? C61 N83 C63 110.9(17) . . ? C61 N83 C62 130.7(17) . . ? C63 N83 C62 118.4(17) . . ? N83 C61 O61 106(2) . . ? N83 C61 C63 35.9(9) . . ? O61 C61 C63 70.2(14) . . ? N83 C63 C61 33.3(10) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.892 _refine_diff_density_min -0.788 _refine_diff_density_rms 0.070 # Attachment '26DHB.CIF' data_4 _database_code_depnum_ccdc_archive 'CCDC 782611' #TrackingRef '26DHB.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H5 O4, C3 H7 N6' _chemical_formula_sum 'C10 H12 N6 O4' _chemical_formula_weight 280.26 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.3720(10) _cell_length_b 8.5490(10) _cell_length_c 20.671(2) _cell_angle_alpha 90.000(7) _cell_angle_beta 114.23 _cell_angle_gamma 90.00 _cell_volume 2316.0(4) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1146 _cell_measurement_theta_min 2.3765 _cell_measurement_theta_max 29.3426 _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9798 _exptl_absorpt_correction_T_max 0.9861 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21344 _diffrn_reflns_av_R_equivalents 0.0849 _diffrn_reflns_av_sigmaI/netI 0.1141 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.24 _reflns_number_total 4184 _reflns_number_gt 1676 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlisPro RED (Oxford Diffraction, 2009)' _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^)+(0.0361P)^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 SHELXL _refine_ls_extinction_coef ? _refine_ls_number_reflns 4184 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1371 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.0984 _refine_ls_wR_factor_gt 0.0838 _refine_ls_goodness_of_fit_ref 0.771 _refine_ls_restrained_S_all 0.771 _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 O12 O 0.66205(17) 0.7318(3) 0.76703(11) 0.0417(7) Uani 1 1 d . . . H12 H 0.6824 0.6698 0.8016 0.063 Uiso 1 1 d R . . O16 O 0.99275(17) 0.6160(2) 0.77392(11) 0.0321(6) Uani 1 1 d . . . H16 H 0.9967 0.5630 0.8092 0.048 Uiso 1 1 d R . . O17A O 0.78219(17) 0.5448(3) 0.85984(10) 0.0401(7) Uani 1 1 d . . . O17B O 0.93869(17) 0.5009(2) 0.86612(10) 0.0340(6) Uani 1 1 d . . . C11 C 0.8289(2) 0.6693(4) 0.77474(15) 0.0177(8) Uani 1 1 d . . . C12 C 0.7364(3) 0.7496(4) 0.74255(17) 0.0239(9) Uani 1 1 d . . . C13 C 0.7168(3) 0.8469(4) 0.68556(16) 0.0286(9) Uani 1 1 d . . . H13 H 0.6536 0.9010 0.6648 0.034 Uiso 1 1 calc R . . C14 C 0.7895(3) 0.8654(4) 0.65872(16) 0.0287(9) Uani 1 1 d . . . H14 H 0.7758 0.9323 0.6192 0.034 Uiso 1 1 calc R . . C15 C 0.8822(3) 0.7877(4) 0.68865(16) 0.0232(8) Uani 1 1 d . . . H15 H 0.9319 0.8009 0.6698 0.028 Uiso 1 1 calc R . . C16 C 0.9013(2) 0.6913(4) 0.74598(16) 0.0189(8) Uani 1 1 d . . . C17 C 0.8510(3) 0.5666(4) 0.83757(15) 0.0258(8) Uani 1 1 d . . . O22 O 0.42951(17) 0.7340(2) 0.53950(11) 0.0343(6) Uani 1 1 d . . . H22 H 0.4566 0.6703 0.5730 0.052 Uiso 1 1 d R . . O26 O 0.73215(16) 0.6172(2) 0.50510(10) 0.0292(6) Uani 1 1 d . . . H26 H 0.7423 0.5590 0.5401 0.044 Uiso 1 1 d R . . O27A O 0.70103(16) 0.4877(2) 0.60232(10) 0.0322(6) Uani 1 1 d . . . O27B O 0.56146(16) 0.5412(2) 0.62064(10) 0.0313(6) Uani 1 1 d . . . C21 C 0.5826(3) 0.6691(4) 0.52571(16) 0.0190(8) Uani 1 1 d . . . C22 C 0.4899(3) 0.7505(4) 0.50368(17) 0.0233(8) Uani 1 1 d . . . C23 C 0.4588(3) 0.8502(4) 0.44636(16) 0.0315(9) Uani 1 1 d . . . H23 H 0.3952 0.9032 0.4316 0.038 Uiso 1 1 calc R . . C24 C 0.5203(3) 0.8729(4) 0.41044(16) 0.0303(9) Uani 1 1 d . . . H24 H 0.4990 0.9430 0.3714 0.036 Uiso 1 1 calc R . . C25 C 0.6116(3) 0.7960(4) 0.43029(16) 0.0267(9) Uani 1 1 d . . . H25 H 0.6532 0.8128 0.4052 0.032 Uiso 1 1 calc R . . C26 C 0.6426(2) 0.6938(4) 0.48711(16) 0.0216(8) Uani 1 1 d . . . C27 C 0.6168(3) 0.5597(4) 0.58626(14) 0.0247(8) Uani 1 1 d . . . N31 N 0.9181(2) 0.7137(3) 1.02296(13) 0.0271(7) Uani 1 1 d . . . H31A H 0.9375 0.6460 1.0581 0.033 Uiso 1 1 d R . . H31B H 0.8571 0.7563 1.0076 0.033 Uiso 1 1 d R . . N32 N 0.95516(19) 0.8517(3) 0.94062(12) 0.0196(7) Uani 1 1 d . . . N33 N 1.00083(18) 0.9745(3) 0.86065(12) 0.0287(7) Uani 1 1 d . . . H33A H 0.9404 1.0194 0.8439 0.034 Uiso 1 1 d R . . H33B H 1.0439 0.9949 0.8414 0.034 Uiso 1 1 d R . . N34 N 1.1203(2) 0.8111(3) 0.93825(13) 0.0240(7) Uani 1 1 d . . . N35 N 1.2316(2) 0.6417(3) 1.02021(14) 0.0325(8) Uani 1 1 d . . . H35A H 1.2779 0.6591 1.0034 0.039 Uiso 1 1 d R . . H35B H 1.2448 0.5768 1.0559 0.039 Uiso 1 1 d R . . N36 N 1.0735(2) 0.6781(3) 1.01946(13) 0.0220(7) Uani 1 1 d . . . H36 H 1.0859 0.6119 1.0570 0.026 Uiso 1 1 d R . . C31 C 0.9812(2) 0.7516(4) 0.99300(16) 0.0181(8) Uani 1 1 d . . . C33 C 1.0269(3) 0.8764(3) 0.91474(15) 0.0217(8) Uani 1 1 d . . . C35 C 1.1417(2) 0.7137(4) 0.99160(17) 0.0229(8) Uani 1 1 d . . . N41 N 0.8139(2) 0.2704(3) 0.70747(13) 0.0284(7) Uani 1 1 d . . . H41A H 0.7910 0.3363 0.6716 0.034 Uiso 1 1 d R . . H41B H 0.8723 0.2219 0.7181 0.034 Uiso 1 1 d R . . N42 N 0.7931(2) 0.1459(3) 0.79989(12) 0.0212(7) Uani 1 1 d . . . N43 N 0.75839(18) 0.0264(3) 0.88615(11) 0.0291(7) Uani 1 1 d . . . H43A H 0.8179 -0.0206 0.8997 0.035 Uiso 1 1 d R . . H43B H 0.7191 0.0082 0.9086 0.035 Uiso 1 1 d R . . N44 N 0.6356(2) 0.1931(3) 0.81358(13) 0.0254(7) Uani 1 1 d . . . N45 N 0.5242(2) 0.3762(3) 0.74097(13) 0.0330(8) Uani 1 1 d . . . H45A H 0.4831 0.3623 0.7624 0.040 Uiso 1 1 d R . . H45B H 0.5082 0.4439 0.7060 0.040 Uiso 1 1 d R . . N46 N 0.6709(2) 0.3228(3) 0.72626(13) 0.0229(7) Uani 1 1 d . . . H46 H 0.6504 0.3943 0.6879 0.027 Uiso 1 1 d R . . C41 C 0.7608(3) 0.2446(4) 0.74534(16) 0.0214(9) Uani 1 1 d . . . C43 C 0.7281(3) 0.1242(4) 0.83198(15) 0.0219(8) Uani 1 1 d . . . C45 C 0.6104(3) 0.2948(4) 0.76148(17) 0.0242(9) 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 O12 0.0364(17) 0.0567(17) 0.0386(14) -0.0078(13) 0.0219(13) -0.0041(13) O16 0.0278(15) 0.0399(15) 0.0289(12) 0.0069(11) 0.0118(11) 0.0075(12) O17A 0.0556(18) 0.0488(17) 0.0243(13) -0.0076(12) 0.0251(13) -0.0245(13) O17B 0.0480(17) 0.0271(14) 0.0194(11) 0.0010(11) 0.0063(11) 0.0055(13) C11 0.022(2) 0.017(2) 0.0127(16) -0.0052(15) 0.0057(15) -0.0028(16) C12 0.025(2) 0.028(2) 0.0230(18) -0.0135(18) 0.0137(17) -0.0057(18) C13 0.027(2) 0.025(2) 0.0256(19) 0.0005(17) 0.0023(17) 0.0091(17) C14 0.044(3) 0.024(2) 0.0174(17) -0.0001(16) 0.0112(18) -0.0013(18) C15 0.030(2) 0.022(2) 0.0225(17) -0.0015(16) 0.0151(16) -0.0032(17) C16 0.026(2) 0.0133(19) 0.0183(17) -0.0010(15) 0.0099(16) 0.0025(16) C17 0.040(2) 0.018(2) 0.0162(17) -0.0063(15) 0.0086(17) -0.0049(17) O22 0.0333(15) 0.0415(16) 0.0369(13) 0.0035(12) 0.0231(12) 0.0031(12) O26 0.0283(15) 0.0360(15) 0.0254(12) 0.0033(11) 0.0130(12) 0.0050(11) O27A 0.0355(15) 0.0298(14) 0.0263(12) 0.0052(11) 0.0076(11) 0.0063(12) O27B 0.0425(15) 0.0327(15) 0.0230(11) 0.0005(11) 0.0179(12) -0.0082(12) C21 0.025(2) 0.013(2) 0.0191(18) -0.0027(15) 0.0098(16) -0.0054(17) C22 0.028(2) 0.025(2) 0.0200(17) -0.0013(17) 0.0135(15) -0.0013(18) C23 0.030(2) 0.031(2) 0.030(2) 0.0019(18) 0.0092(18) 0.0070(17) C24 0.038(2) 0.027(2) 0.0239(19) 0.0067(16) 0.0106(18) 0.0070(18) C25 0.034(2) 0.029(2) 0.0209(18) -0.0028(16) 0.0151(16) -0.0084(18) C26 0.021(2) 0.022(2) 0.0207(18) -0.0034(16) 0.0071(16) -0.0023(16) C27 0.036(2) 0.021(2) 0.0140(16) -0.0037(15) 0.0075(16) -0.0060(18) N31 0.0250(18) 0.0346(17) 0.0247(15) 0.0091(13) 0.0132(13) 0.0062(14) N32 0.0231(17) 0.0218(18) 0.0148(14) 0.0049(12) 0.0088(13) -0.0029(13) N33 0.0297(17) 0.0314(17) 0.0272(14) 0.0070(14) 0.0139(13) 0.0015(14) N34 0.0266(19) 0.0246(18) 0.0223(15) 0.0052(14) 0.0114(14) -0.0003(14) N35 0.0278(19) 0.037(2) 0.0343(16) 0.0084(14) 0.0139(15) 0.0055(15) N36 0.0267(18) 0.0220(17) 0.0195(14) 0.0039(13) 0.0118(14) -0.0014(14) C31 0.021(2) 0.019(2) 0.0144(16) -0.0054(16) 0.0076(15) -0.0028(17) C33 0.033(2) 0.015(2) 0.0147(17) -0.0029(16) 0.0072(17) -0.0068(17) C35 0.017(2) 0.024(2) 0.0240(18) -0.0038(17) 0.0048(16) -0.0026(17) N41 0.0295(18) 0.0328(18) 0.0244(15) 0.0093(13) 0.0124(14) 0.0043(14) N42 0.0255(18) 0.0208(18) 0.0175(14) 0.0011(13) 0.0091(13) -0.0013(13) N43 0.0319(17) 0.0339(18) 0.0252(14) 0.0125(14) 0.0154(13) 0.0063(14) N44 0.0263(19) 0.0257(18) 0.0206(15) 0.0044(14) 0.0061(14) 0.0000(14) N45 0.029(2) 0.040(2) 0.0312(16) 0.0125(14) 0.0133(15) 0.0089(15) N46 0.0249(18) 0.0232(17) 0.0173(14) 0.0048(13) 0.0054(14) 0.0025(14) C41 0.025(2) 0.021(2) 0.0138(16) -0.0015(17) 0.0044(15) -0.0065(17) C43 0.030(2) 0.018(2) 0.0143(16) -0.0041(15) 0.0051(17) -0.0054(17) C45 0.021(2) 0.027(2) 0.0230(18) -0.0049(17) 0.0080(17) -0.0019(17) _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 O12 C12 1.365(4) . ? O16 C16 1.361(4) . ? O17A C17 1.265(3) . ? O17B C17 1.281(3) . ? C11 C12 1.398(4) . ? C11 C16 1.408(4) . ? C11 C17 1.490(4) . ? C12 C13 1.373(4) . ? C13 C14 1.378(4) . ? C14 C15 1.387(4) . ? C15 C16 1.376(4) . ? O22 C22 1.360(4) . ? O26 C26 1.353(4) . ? O27A C27 1.275(3) . ? O27B C27 1.275(3) . ? C21 C22 1.403(4) . ? C21 C26 1.411(4) . ? C21 C27 1.476(4) . ? C22 C23 1.377(4) . ? C23 C24 1.382(4) . ? C24 C25 1.371(4) . ? C25 C26 1.383(4) . ? N31 C31 1.331(4) . ? N32 C31 1.308(3) . ? N32 C33 1.358(4) . ? N33 C33 1.323(3) . ? N34 C35 1.314(4) . ? N34 C33 1.348(4) . ? N35 C35 1.331(4) . ? N36 C35 1.359(4) . ? N36 C31 1.363(4) . ? N41 C41 1.316(4) . ? N42 C41 1.330(3) . ? N42 C43 1.362(4) . ? N43 C43 1.320(3) . ? N44 C45 1.314(4) . ? N44 C43 1.357(4) . ? N45 C45 1.330(4) . ? N46 C41 1.362(4) . ? N46 C45 1.364(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 C11 C16 117.2(3) . . ? C12 C11 C17 121.7(3) . . ? C16 C11 C17 121.1(3) . . ? O12 C12 C13 118.0(3) . . ? O12 C12 C11 120.3(3) . . ? C13 C12 C11 121.7(3) . . ? C12 C13 C14 119.5(3) . . ? C13 C14 C15 120.9(3) . . ? C16 C15 C14 119.1(3) . . ? O16 C16 C15 117.8(3) . . ? O16 C16 C11 120.7(3) . . ? C15 C16 C11 121.5(3) . . ? O17A C17 O17B 122.4(3) . . ? O17A C17 C11 119.0(3) . . ? O17B C17 C11 118.5(3) . . ? C22 C21 C26 117.5(3) . . ? C22 C21 C27 122.1(3) . . ? C26 C21 C27 120.4(3) . . ? O22 C22 C23 118.6(3) . . ? O22 C22 C21 120.3(3) . . ? C23 C22 C21 121.1(3) . . ? C22 C23 C24 119.7(3) . . ? C25 C24 C23 121.1(3) . . ? C24 C25 C26 119.5(3) . . ? O26 C26 C25 118.6(3) . . ? O26 C26 C21 120.3(3) . . ? C25 C26 C21 121.1(3) . . ? O27A C27 O27B 122.5(3) . . ? O27A C27 C21 118.5(3) . . ? O27B C27 C21 119.0(3) . . ? C31 N32 C33 115.0(3) . . ? C35 N34 C33 114.8(3) . . ? C35 N36 C31 118.6(3) . . ? N32 C31 N31 121.8(3) . . ? N32 C31 N36 122.3(3) . . ? N31 C31 N36 116.0(3) . . ? N33 C33 N34 117.5(3) . . ? N33 C33 N32 115.7(3) . . ? N34 C33 N32 126.8(3) . . ? N34 C35 N35 121.0(3) . . ? N34 C35 N36 122.5(3) . . ? N35 C35 N36 116.5(3) . . ? C41 N42 C43 115.4(3) . . ? C45 N44 C43 115.2(3) . . ? C41 N46 C45 119.7(3) . . ? N41 C41 N42 121.7(3) . . ? N41 C41 N46 117.2(3) . . ? N42 C41 N46 121.1(3) . . ? N43 C43 N44 117.2(3) . . ? N43 C43 N42 116.5(3) . . ? N44 C43 N42 126.3(3) . . ? N44 C45 N45 121.0(3) . . ? N44 C45 N46 122.1(3) . . ? N45 C45 N46 116.9(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.261 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.050 # Attachment '2OH.CIF' data_5 _database_code_depnum_ccdc_archive 'CCDC 782612' #TrackingRef '2OH.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; 2(C3 H7 N6), 2(C7 H5 O3), (C2 H3 N) ; _chemical_formula_sum 'C22 H27 N13 O6' _chemical_formula_weight 569.57 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.691(8) _cell_length_b 8.577(4) _cell_length_c 20.692(8) _cell_angle_alpha 90.00 _cell_angle_beta 117.83(3) _cell_angle_gamma 90.00 _cell_volume 2620(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1377 _cell_measurement_theta_min 5.115 _cell_measurement_theta_max 39.455 _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9848 _exptl_absorpt_correction_T_max 0.9902 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5980 _diffrn_reflns_av_R_equivalents 0.0539 _diffrn_reflns_av_sigmaI/netI 0.2064 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 3 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4203 _reflns_number_gt 1247 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlisPro RED (Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXTL (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1997)' _computing_molecular_graphics 'XP Suite SHELXTL' _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^)+(0.0873P)^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 SHELXL _refine_ls_extinction_coef ? _refine_ls_number_reflns 4203 _refine_ls_number_parameters 371 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1660 _refine_ls_R_factor_gt 0.0712 _refine_ls_wR_factor_ref 0.1805 _refine_ls_wR_factor_gt 0.1620 _refine_ls_goodness_of_fit_ref 0.689 _refine_ls_restrained_S_all 0.689 _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 N31 N 0.3562(2) 0.2574(5) 0.69618(19) 0.0538(13) Uani 1 1 d . . . H31B H 0.3423 0.2012 0.7239 0.065 Uiso 1 1 d R . . H32B H 0.4075 0.3049 0.7142 0.065 Uiso 1 1 d R . . N32 N 0.2205(3) 0.1953(5) 0.60052(19) 0.0466(12) Uani 1 1 d . . . H32 H 0.2081 0.1406 0.6295 0.056 Uiso 1 1 d R . . N33 N 0.0845(3) 0.1271(6) 0.5076(2) 0.0787(18) Uani 1 1 d . . . H33B H 0.0437 0.1298 0.4625 0.094 Uiso 1 1 d R . . H33A H 0.0755 0.0734 0.5387 0.094 Uiso 1 1 d R . . N34 N 0.1766(3) 0.2885(5) 0.48286(19) 0.0492(13) Uani 1 1 d . . . N35 N 0.2790(3) 0.4466(5) 0.4700(2) 0.0586(14) Uani 1 1 d . . . H35A H 0.2415 0.4559 0.4243 0.070 Uiso 1 1 d R . . H35B H 0.3304 0.4935 0.4880 0.070 Uiso 1 1 d R . . N36 N 0.3222(3) 0.3545(5) 0.5836(2) 0.0450(12) Uani 1 1 d . . . N41 N 0.7030(3) 0.8609(6) 0.6397(2) 0.0776(17) Uani 1 1 d . . . H41B H 0.7391 0.8495 0.6856 0.093 Uiso 1 1 d R . . H41A H 0.7178 0.9212 0.6138 0.093 Uiso 1 1 d R . . N42 N 0.6003(3) 0.6920(5) 0.6474(2) 0.0469(13) Uani 1 1 d . . . N43 N 0.4925(3) 0.5300(5) 0.6450(2) 0.0565(14) Uani 1 1 d . . . H43A H 0.5253 0.5160 0.6912 0.068 Uiso 1 1 d R . . H43B H 0.4412 0.4831 0.6222 0.068 Uiso 1 1 d R . . N44 N 0.4623(3) 0.6380(5) 0.53666(19) 0.0427(12) Uani 1 1 d . . . N45 N 0.4432(3) 0.7637(5) 0.43112(19) 0.0560(13) Uani 1 1 d . . . H45B H 0.4625 0.8276 0.4094 0.067 Uiso 1 1 d R . . H45A H 0.3918 0.7182 0.4069 0.067 Uiso 1 1 d R . . N46 N 0.5732(3) 0.8092(5) 0.5378(2) 0.0518(13) Uani 1 1 d . . . H46 H 0.5906 0.8716 0.5143 0.062 Uiso 1 1 d R . . C31 C 0.2993(3) 0.2707(6) 0.6264(2) 0.0347(14) Uani 1 1 d . . . C33 C 0.1599(4) 0.2047(7) 0.5286(3) 0.0481(16) Uani 1 1 d . . . C35 C 0.2570(4) 0.3590(6) 0.5131(3) 0.0415(14) Uani 1 1 d . . . C41 C 0.6256(4) 0.7862(7) 0.6093(3) 0.0511(16) Uani 1 1 d . . . C43 C 0.5209(4) 0.6238(7) 0.6089(3) 0.0405(15) Uani 1 1 d . . . C45 C 0.4931(4) 0.7352(6) 0.5023(3) 0.0396(14) Uani 1 1 d . . . O12 O 0.2705(2) 0.6033(4) 0.32943(16) 0.0595(11) Uani 1 1 d . . . H12 H 0.2698 0.5459 0.2975 0.089 Uiso 1 1 d R . . O17A O 0.0662(2) 0.5303(4) 0.11973(16) 0.0576(11) Uani 1 1 d . . . O17B O 0.2057(2) 0.4761(4) 0.20482(16) 0.0527(11) Uani 1 1 d . . . C11 C 0.1205(4) 0.6567(6) 0.2339(2) 0.0402(14) Uani 1 1 d . . . C12 C 0.1906(4) 0.6809(6) 0.3035(3) 0.0442(15) Uani 1 1 d . . . C13 C 0.1797(5) 0.7863(7) 0.3504(3) 0.0643(19) Uani 1 1 d . . . H13 H 0.2267 0.8019 0.3973 0.077 Uiso 1 1 calc R . . C14 C 0.1010(5) 0.8658(8) 0.3277(3) 0.075(2) Uani 1 1 d . . . H14 H 0.0947 0.9374 0.3588 0.089 Uiso 1 1 calc R . . C15 C 0.0314(4) 0.8416(7) 0.2600(4) 0.071(2) Uani 1 1 d . . . H4A H -0.0228 0.8953 0.2454 0.086 Uiso 1 1 calc R . . C16 C 0.0401(4) 0.7381(7) 0.2126(3) 0.0603(17) Uani 1 1 d . . . H15 H -0.0081 0.7228 0.1662 0.072 Uiso 1 1 calc R . . C17 C 0.1318(4) 0.5474(6) 0.1827(3) 0.0420(15) Uani 1 1 d . . . O22 O 0.4695(2) 0.8961(5) 0.71617(17) 0.0656(12) Uani 1 1 d . . . H22 H 0.4790 0.9543 0.6891 0.098 Uiso 1 1 d R . . O27A O 0.3229(3) 0.9949(5) 0.50071(18) 0.0755(14) Uani 1 1 d . . . O27B O 0.4493(3) 1.0182(5) 0.6030(2) 0.0722(13) Uani 1 1 d . . . C21 C 0.3350(4) 0.8579(6) 0.6045(2) 0.0376(14) Uani 1 1 d . . . C22 C 0.3884(4) 0.8268(6) 0.6782(3) 0.0447(15) Uani 1 1 d . . . C23 C 0.3563(5) 0.7283(7) 0.7146(3) 0.070(2) Uani 1 1 d . . . H23 H 0.3916 0.7094 0.7643 0.084 Uiso 1 1 calc R . . C24 C 0.2745(5) 0.6606(7) 0.6780(4) 0.076(2) Uani 1 1 d . . . H24 H 0.2540 0.5932 0.7023 0.091 Uiso 1 1 calc R . . C25 C 0.2214(4) 0.6904(8) 0.6053(4) 0.077(2) Uani 1 1 d . . . H25 H 0.1644 0.6450 0.5804 0.093 Uiso 1 1 calc R . . C26 C 0.2527(4) 0.7885(7) 0.5687(3) 0.0631(18) Uani 1 1 d . . . H26 H 0.2169 0.8069 0.5190 0.076 Uiso 1 1 calc R . . C27 C 0.3723(4) 0.9628(7) 0.5655(3) 0.0513(17) Uani 1 1 d . . . N51 N -0.1457(4) 0.6287(7) 0.2940(3) 0.088(2) Uani 1 1 d . . . C51 C 0.0117(4) 0.5915(9) 0.4073(3) 0.122(3) Uani 1 1 d . . . H51B H 0.0183 0.6647 0.4446 0.183 Uiso 1 1 calc R . . H1B H 0.0578 0.6098 0.3929 0.183 Uiso 1 1 calc R . . H51A H 0.0175 0.4873 0.4260 0.183 Uiso 1 1 calc R . . C52 C -0.0781(5) 0.6106(8) 0.3437(4) 0.073(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 N31 0.047(3) 0.079(4) 0.034(2) 0.007(2) 0.017(2) -0.010(3) N32 0.050(3) 0.060(3) 0.027(2) 0.009(2) 0.016(2) 0.000(3) N33 0.069(4) 0.114(5) 0.036(3) 0.010(3) 0.010(3) -0.037(4) N34 0.050(3) 0.061(3) 0.029(2) 0.006(2) 0.012(2) -0.002(3) N35 0.065(3) 0.076(4) 0.038(2) 0.012(2) 0.026(2) 0.000(3) N36 0.054(3) 0.050(3) 0.029(2) 0.008(2) 0.017(2) 0.006(3) N41 0.076(4) 0.106(5) 0.049(3) -0.004(3) 0.028(3) -0.024(4) N42 0.054(3) 0.054(3) 0.034(2) -0.006(2) 0.022(3) -0.010(3) N43 0.066(3) 0.070(3) 0.036(2) 0.006(2) 0.025(2) -0.007(3) N44 0.048(3) 0.051(3) 0.034(2) -0.001(2) 0.023(2) -0.007(3) N45 0.055(3) 0.082(4) 0.033(2) 0.009(2) 0.023(2) 0.004(3) N46 0.051(3) 0.070(4) 0.040(3) 0.000(2) 0.025(2) -0.006(3) C31 0.024(3) 0.046(4) 0.028(3) -0.007(3) 0.007(3) -0.002(3) C33 0.045(4) 0.056(4) 0.044(4) 0.016(3) 0.021(3) 0.010(4) C35 0.051(4) 0.039(4) 0.041(3) 0.002(3) 0.027(3) 0.002(3) C41 0.034(4) 0.066(5) 0.046(4) -0.014(3) 0.012(3) -0.006(4) C43 0.045(4) 0.044(4) 0.036(3) -0.009(3) 0.022(3) 0.008(3) C45 0.032(4) 0.050(4) 0.035(3) -0.012(3) 0.013(3) 0.002(3) O12 0.062(3) 0.080(3) 0.033(2) -0.0060(19) 0.0189(19) 0.011(3) O17A 0.037(2) 0.094(3) 0.032(2) -0.014(2) 0.0080(17) 0.002(2) O17B 0.049(3) 0.070(3) 0.038(2) -0.0024(18) 0.0189(19) 0.016(2) C11 0.042(4) 0.044(4) 0.032(3) 0.000(3) 0.016(3) -0.005(3) C12 0.053(4) 0.047(4) 0.038(3) 0.004(3) 0.025(3) 0.002(3) C13 0.098(6) 0.062(5) 0.043(3) -0.014(3) 0.041(4) -0.016(4) C14 0.101(6) 0.079(5) 0.069(5) 0.005(4) 0.061(5) 0.029(5) C15 0.085(5) 0.068(5) 0.080(5) 0.006(4) 0.055(5) 0.017(4) C16 0.077(5) 0.055(4) 0.060(4) 0.008(3) 0.042(4) 0.014(4) C17 0.046(4) 0.045(4) 0.038(3) -0.003(3) 0.022(3) 0.000(3) O22 0.068(3) 0.089(3) 0.035(2) 0.001(2) 0.020(2) 0.004(3) O27A 0.102(3) 0.094(3) 0.036(2) 0.016(2) 0.037(2) 0.015(3) O27B 0.087(3) 0.077(3) 0.077(3) 0.000(2) 0.059(3) -0.012(3) C21 0.038(4) 0.044(4) 0.032(3) -0.004(3) 0.017(3) 0.001(3) C22 0.038(4) 0.053(4) 0.036(3) -0.015(3) 0.012(3) 0.001(3) C23 0.125(7) 0.057(5) 0.056(4) 0.016(4) 0.065(5) 0.018(5) C24 0.117(6) 0.055(5) 0.085(5) -0.007(4) 0.070(5) -0.013(5) C25 0.063(5) 0.088(6) 0.098(5) -0.024(4) 0.053(5) -0.020(4) C26 0.062(5) 0.077(5) 0.051(4) -0.025(3) 0.026(4) -0.018(4) C27 0.068(5) 0.044(4) 0.048(4) -0.002(3) 0.033(4) 0.007(4) N51 0.089(5) 0.096(5) 0.074(4) 0.004(4) 0.033(3) 0.012(4) C51 0.096(6) 0.164(8) 0.074(5) 0.029(5) 0.013(5) 0.006(6) C52 0.093(6) 0.071(5) 0.079(5) 0.011(5) 0.061(5) 0.008(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 N31 C31 1.311(5) . ? N31 H31B 0.8600 . ? N31 H32B 0.8599 . ? N32 C31 1.334(5) . ? N32 C33 1.356(5) . ? N32 H32 0.8600 . ? N33 C33 1.306(6) . ? N33 H33B 0.8599 . ? N33 H33A 0.8601 . ? N34 C33 1.318(6) . ? N34 C35 1.333(6) . ? N35 C35 1.341(6) . ? N35 H35A 0.8600 . ? N35 H35B 0.8600 . ? N36 C31 1.327(6) . ? N36 C35 1.354(6) . ? N41 C41 1.311(6) . ? N41 H41B 0.8600 . ? N41 H41A 0.8600 . ? N42 C43 1.321(6) . ? N42 C41 1.326(6) . ? N43 C43 1.327(6) . ? N43 H43A 0.8600 . ? N43 H43B 0.8600 . ? N44 C45 1.344(6) . ? N44 C43 1.357(5) . ? N45 C45 1.333(5) . ? N45 H45B 0.8601 . ? N45 H45A 0.8600 . ? N46 C41 1.336(6) . ? N46 C45 1.346(6) . ? N46 H46 0.8600 . ? O12 C12 1.358(5) . ? O12 H12 0.8201 . ? O17A C17 1.258(5) . ? O17B C17 1.257(5) . ? C11 C12 1.382(6) . ? C11 C16 1.389(6) . ? C11 C17 1.492(7) . ? C12 C13 1.399(7) . ? C13 C14 1.355(7) . ? C13 H13 0.9300 . ? C14 C15 1.355(7) . ? C14 H14 0.9300 . ? C15 C16 1.380(7) . ? C15 H4A 0.9300 . ? C16 H15 0.9300 . ? O22 C22 1.345(6) . ? O22 H22 0.8201 . ? O27A C27 1.233(6) . ? O27B C27 1.245(6) . ? C21 C26 1.356(6) . ? C21 C22 1.385(6) . ? C21 C27 1.523(7) . ? C22 C23 1.395(7) . ? C23 C24 1.345(7) . ? C23 H23 0.9300 . ? C24 C25 1.368(7) . ? C24 H24 0.9300 . ? C25 C26 1.387(8) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? N51 C52 1.128(7) . ? C51 C52 1.470(8) . ? C51 H51B 0.9600 . ? C51 H1B 0.9600 . ? C51 H51A 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C31 N31 H31B 120.0 . . ? C31 N31 H32B 120.0 . . ? H31B N31 H32B 120.0 . . ? C31 N32 C33 120.2(4) . . ? C31 N32 H32 119.9 . . ? C33 N32 H32 119.9 . . ? C33 N33 H33B 120.0 . . ? C33 N33 H33A 120.0 . . ? H33B N33 H33A 120.0 . . ? C33 N34 C35 114.5(5) . . ? C35 N35 H35A 119.9 . . ? C35 N35 H35B 120.1 . . ? H35A N35 H35B 120.0 . . ? C31 N36 C35 113.5(5) . . ? C41 N41 H41B 119.9 . . ? C41 N41 H41A 120.1 . . ? H41B N41 H41A 120.0 . . ? C43 N42 C41 114.8(5) . . ? C43 N43 H43A 120.0 . . ? C43 N43 H43B 120.0 . . ? H43A N43 H43B 120.0 . . ? C45 N44 C43 112.4(5) . . ? C45 N45 H45B 120.0 . . ? C45 N45 H45A 120.0 . . ? H45B N45 H45A 120.0 . . ? C41 N46 C45 120.3(5) . . ? C41 N46 H46 119.9 . . ? C45 N46 H46 119.8 . . ? N31 C31 N36 119.7(5) . . ? N31 C31 N32 118.2(5) . . ? N36 C31 N32 122.1(4) . . ? N33 C33 N34 122.1(5) . . ? N33 C33 N32 116.4(5) . . ? N34 C33 N32 121.4(5) . . ? N34 C35 N35 118.1(5) . . ? N34 C35 N36 128.2(5) . . ? N35 C35 N36 113.7(5) . . ? N41 C41 N42 121.9(6) . . ? N41 C41 N46 116.6(6) . . ? N42 C41 N46 121.5(5) . . ? N42 C43 N43 116.9(5) . . ? N42 C43 N44 128.9(5) . . ? N43 C43 N44 114.3(5) . . ? N45 C45 N44 120.2(5) . . ? N45 C45 N46 117.8(5) . . ? N44 C45 N46 122.1(5) . . ? C12 O12 H12 109.4 . . ? C12 C11 C16 118.5(5) . . ? C12 C11 C17 120.6(5) . . ? C16 C11 C17 120.9(5) . . ? O12 C12 C11 122.4(5) . . ? O12 C12 C13 117.7(5) . . ? C11 C12 C13 119.9(6) . . ? C14 C13 C12 120.3(6) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 C13 120.4(6) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 120.6(6) . . ? C14 C15 H4A 119.7 . . ? C16 C15 H4A 119.7 . . ? C15 C16 C11 120.3(6) . . ? C15 C16 H15 119.9 . . ? C11 C16 H15 119.9 . . ? O17B C17 O17A 123.5(5) . . ? O17B C17 C11 118.3(5) . . ? O17A C17 C11 118.2(5) . . ? C22 O22 H22 109.4 . . ? C26 C21 C22 119.0(5) . . ? C26 C21 C27 122.0(5) . . ? C22 C21 C27 119.0(5) . . ? O22 C22 C21 120.9(5) . . ? O22 C22 C23 119.1(5) . . ? C21 C22 C23 119.9(6) . . ? C24 C23 C22 120.2(6) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C23 C24 C25 120.3(7) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C24 C25 C26 119.8(6) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? C21 C26 C25 120.8(6) . . ? C21 C26 H26 119.6 . . ? C25 C26 H26 119.6 . . ? O27A C27 O27B 124.4(6) . . ? O27A C27 C21 118.5(6) . . ? O27B C27 C21 117.0(5) . . ? C52 C51 H51B 109.5 . . ? C52 C51 H1B 109.5 . . ? H51B C51 H1B 109.5 . . ? C52 C51 H51A 109.5 . . ? H51B C51 H51A 109.5 . . ? H1B C51 H51A 109.5 . . ? N51 C52 C51 177.7(8) . . ? _diffrn_measured_fraction_theta_max 0.912 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.911 _refine_diff_density_max 0.358 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.078 # Attachment '4OH.CIF' data_6 _database_code_depnum_ccdc_archive 'CCDC 782613' #TrackingRef '4OH.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C3 H7 N6, C7 H5 O3, 2(H2 O)' _chemical_formula_sum 'C10 H16 N6 O5' _chemical_formula_weight 300.29 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 7.5710 _cell_length_b 10.8570(10) _cell_length_c 16.4770(10) _cell_angle_alpha 87.120(5) _cell_angle_beta 85.510(5) _cell_angle_gamma 82.630(5) _cell_volume 1337.96(15) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 784 _cell_measurement_theta_min 2.3451 _cell_measurement_theta_max 29.6476 _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.491 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9809 _exptl_absorpt_correction_T_max 0.9880 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25272 _diffrn_reflns_av_R_equivalents 0.0560 _diffrn_reflns_av_sigmaI/netI 0.0528 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 25.23 _reflns_number_total 4818 _reflns_number_gt 2815 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlisPro RED (Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXTL (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1997)' _computing_molecular_graphics 'XP Suite SHELXTL' _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^)+(0.0550P)^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 SHELXL _refine_ls_extinction_coef ? _refine_ls_number_reflns 4818 _refine_ls_number_parameters 379 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0837 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1119 _refine_ls_wR_factor_gt 0.1032 _refine_ls_goodness_of_fit_ref 0.944 _refine_ls_restrained_S_all 0.957 _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 N31 N 0.3446(2) 0.41244(17) 0.09539(11) 0.0430(5) Uani 1 1 d . . . H31B H 0.2842 0.4752 0.0723 0.052 Uiso 1 1 d R . . H31A H 0.3495 0.4082 0.1474 0.052 Uiso 1 1 d R . . N32 N 0.4256(2) 0.32586(15) -0.02888(11) 0.0326(4) Uani 1 1 d . . . N33 N 0.5145(3) 0.22868(17) -0.14654(11) 0.0474(6) Uani 1 1 d . . . H34B H 0.4552 0.2898 -0.1718 0.057 Uiso 1 1 d R . . H33B H 0.5714 0.1682 -0.1734 0.057 Uiso 1 1 d R . . N34 N 0.6137(2) 0.12899(15) -0.03080(10) 0.0328(5) Uani 1 1 d . . . N35 N 0.6985(2) 0.03944(16) 0.09180(11) 0.0386(5) Uani 1 1 d . . . H45A H 0.7574 -0.0226 0.0672 0.046 Uiso 1 1 d R . . H45B H 0.6961 0.0418 0.1440 0.046 Uiso 1 1 d R . . N36 N 0.5224(2) 0.22646(16) 0.09226(10) 0.0325(4) Uani 1 1 d D . . H36 H 0.5202 0.2168 0.1559 0.039 Uiso 1 1 d RD . . C31 C 0.4298(3) 0.32250(19) 0.05098(13) 0.0313(5) Uani 1 1 d . . . C33 C 0.5181(3) 0.22771(19) -0.06712(13) 0.0304(5) Uani 1 1 d . . . C35 C 0.6116(3) 0.13086(19) 0.04960(13) 0.0294(5) Uani 1 1 d . . . N41 N 0.7951(2) 0.45794(16) 0.10648(11) 0.0412(5) Uani 1 1 d . . . H41B H 0.7386 0.5207 0.0816 0.049 Uiso 1 1 d R . . H41A H 0.7948 0.4553 0.1587 0.049 Uiso 1 1 d R . . N42 N 0.8847(2) 0.36853(15) -0.01566(10) 0.0324(4) Uani 1 1 d . . . N43 N 0.9901(2) 0.26900(17) -0.13183(11) 0.0443(5) Uani 1 1 d . . . H43B H 1.0507 0.2080 -0.1569 0.053 Uiso 1 1 d R . . H43A H 0.9353 0.3298 -0.1591 0.053 Uiso 1 1 d R . . N44 N 1.0708(2) 0.17068(16) -0.01309(10) 0.0328(4) Uani 1 1 d . . . N45 N 1.1458(2) 0.08343(17) 0.11165(11) 0.0438(5) Uani 1 1 d . . . H26A H 1.2082 0.0215 0.0883 0.053 Uiso 1 1 d R . . H26B H 1.1383 0.0866 0.1639 0.053 Uiso 1 1 d R . . N46 N 0.9675(2) 0.26973(16) 0.10815(10) 0.0344(5) Uani 1 1 d D . . H46 H 0.9585 0.2758 0.1700 0.041 Uiso 1 1 d RD . . C41 C 0.8825(3) 0.36629(19) 0.06467(13) 0.0296(5) Uani 1 1 d . . . C43 C 0.9813(3) 0.26939(19) -0.05195(13) 0.0312(5) Uani 1 1 d . . . C45 C 1.0619(3) 0.17311(19) 0.06739(13) 0.0313(5) Uani 1 1 d . . . O14 O 1.0186(2) 0.26473(15) 0.64710(9) 0.0620(5) Uani 1 1 d . . . H14 H 0.9535 0.3351 0.6638 0.093 Uiso 1 1 d R . . O17A O 0.9534(2) 0.31117(14) 0.26445(9) 0.0490(5) Uani 1 1 d . . . O17B O 1.0456(2) 0.11000(14) 0.28191(9) 0.0482(5) Uani 1 1 d . . . C11 C 1.0019(3) 0.23243(19) 0.39850(13) 0.0321(5) Uani 1 1 d . . . C12 C 1.0792(3) 0.1365(2) 0.44791(13) 0.0386(6) Uani 1 1 d . . . H12 H 1.1297 0.0626 0.4247 0.046 Uiso 1 1 calc R . . C13 C 1.0829(3) 0.1483(2) 0.53022(14) 0.0458(6) Uani 1 1 d . . . H13 H 1.1356 0.0829 0.5623 0.055 Uiso 1 1 calc R . . C14 C 1.0081(3) 0.2576(2) 0.56557(13) 0.0372(6) Uani 1 1 d . . . C15 C 0.9287(3) 0.3537(2) 0.51748(13) 0.0386(6) Uani 1 1 d . . . H15 H 0.8769 0.4271 0.5410 0.046 Uiso 1 1 calc R . . C16 C 0.9262(3) 0.34132(19) 0.43535(13) 0.0361(6) Uani 1 1 d . . . H16 H 0.8729 0.4068 0.4036 0.043 Uiso 1 1 calc R . . C17 C 1.0006(3) 0.2171(2) 0.30934(13) 0.0362(6) Uani 1 1 d . . . O24 O 0.4989(2) 0.23943(15) 0.63302(9) 0.0579(5) Uani 1 1 d . . . H24 H 0.5499 0.1694 0.6539 0.087 Uiso 1 1 d R . . O27A O 0.4404(2) 0.38646(14) 0.25993(9) 0.0490(5) Uani 1 1 d . . . O27B O 0.5284(2) 0.18473(14) 0.25052(9) 0.0510(5) Uani 1 1 d . . . C21 C 0.4943(3) 0.26668(19) 0.38164(13) 0.0315(5) Uani 1 1 d . . . C22 C 0.5698(3) 0.1579(2) 0.42021(13) 0.0344(6) Uani 1 1 d . . . H22 H 0.6184 0.0911 0.3890 0.041 Uiso 1 1 calc R . . C23 C 0.5741(3) 0.1471(2) 0.50301(13) 0.0366(6) Uani 1 1 d . . . H23 H 0.6269 0.0739 0.5275 0.044 Uiso 1 1 calc R . . C24 C 0.5004(3) 0.2445(2) 0.55052(13) 0.0356(6) Uani 1 1 d . . . C25 C 0.4251(3) 0.3538(2) 0.51324(14) 0.0422(6) Uani 1 1 d . . . H25 H 0.3760 0.4201 0.5448 0.051 Uiso 1 1 calc R . . C26 C 0.4226(3) 0.3647(2) 0.43054(13) 0.0387(6) Uani 1 1 d . . . H26 H 0.3721 0.4387 0.4063 0.046 Uiso 1 1 calc R . . C27 C 0.4879(3) 0.2794(2) 0.29213(14) 0.0371(6) Uani 1 1 d . . . O91 O 0.3412(2) 0.42455(15) -0.25912(10) 0.0604(5) Uani 1 1 d . . . H91A H 0.4253 0.4834 -0.2641 0.091 Uiso 1 1 d R . . H91B H 0.3628 0.3811 -0.2944 0.091 Uiso 1 1 d R . . O93 O 0.1108(2) 0.53430(14) 0.26968(9) 0.0497(5) Uani 1 1 d . . . H93B H 0.0375 0.4824 0.2692 0.075 Uiso 1 1 d R . . H93A H 0.2180 0.4956 0.2722 0.075 Uiso 1 1 d R . . O90 O 0.8250(2) -0.07150(15) 0.24744(9) 0.0593(5) Uani 1 1 d . . . H92A H 0.8443 -0.1270 0.2847 0.089 Uiso 1 1 d R . . H90A H 0.8865 -0.0149 0.2636 0.089 Uiso 1 1 d R . . O92 O 0.3718(2) -0.03815(14) 0.28097(9) 0.0496(5) Uani 1 1 d . . . H92B H 0.2616 0.0035 0.2872 0.074 Uiso 1 1 d R . . H0AA H 0.4448 0.0157 0.2764 0.074 Uiso 1 1 d 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 N31 0.0547(13) 0.0364(12) 0.0328(11) -0.0046(9) -0.0035(9) 0.0147(10) N32 0.0397(12) 0.0271(10) 0.0298(11) -0.0001(8) -0.0050(9) 0.0015(9) N33 0.0713(15) 0.0372(12) 0.0281(12) -0.0027(9) -0.0088(10) 0.0181(10) N34 0.0401(12) 0.0280(10) 0.0290(11) -0.0003(8) -0.0059(8) 0.0024(9) N35 0.0491(13) 0.0321(11) 0.0317(11) -0.0023(9) -0.0065(9) 0.0080(9) N36 0.0385(11) 0.0293(10) 0.0277(10) -0.0023(8) -0.0029(8) 0.0043(9) C31 0.0324(13) 0.0268(12) 0.0343(14) 0.0021(10) -0.0046(10) -0.0021(10) C33 0.0354(13) 0.0257(12) 0.0297(14) 0.0016(10) -0.0046(10) -0.0020(10) C35 0.0309(13) 0.0239(12) 0.0336(14) 0.0002(10) -0.0045(10) -0.0031(10) N41 0.0537(13) 0.0335(11) 0.0327(11) -0.0021(9) -0.0055(9) 0.0105(9) N42 0.0390(11) 0.0278(10) 0.0285(11) -0.0011(8) -0.0038(8) 0.0042(9) N43 0.0632(14) 0.0372(12) 0.0266(12) -0.0021(9) -0.0027(9) 0.0166(10) N44 0.0400(12) 0.0277(10) 0.0290(11) -0.0017(8) -0.0023(9) 0.0022(9) N45 0.0553(13) 0.0383(12) 0.0330(11) -0.0015(9) -0.0102(10) 0.0164(10) N46 0.0419(12) 0.0316(11) 0.0273(10) -0.0025(8) -0.0051(9) 0.0064(9) C41 0.0311(13) 0.0240(12) 0.0336(14) -0.0022(10) -0.0045(10) -0.0015(10) C43 0.0344(14) 0.0281(13) 0.0304(14) -0.0002(10) -0.0035(10) -0.0006(11) C45 0.0327(13) 0.0254(12) 0.0351(14) -0.0031(10) -0.0035(10) -0.0003(10) O14 0.0979(15) 0.0489(11) 0.0322(10) -0.0050(8) -0.0145(9) 0.0249(10) O17A 0.0749(13) 0.0365(10) 0.0325(9) -0.0011(7) -0.0127(8) 0.0104(9) O17B 0.0684(12) 0.0363(10) 0.0375(10) -0.0095(8) -0.0103(8) 0.0097(9) C11 0.0334(13) 0.0296(12) 0.0321(13) -0.0019(10) -0.0028(10) 0.0015(10) C12 0.0491(16) 0.0301(13) 0.0335(14) -0.0054(10) -0.0061(11) 0.0104(11) C13 0.0611(17) 0.0336(14) 0.0382(15) 0.0022(11) -0.0113(12) 0.0146(12) C14 0.0484(15) 0.0327(13) 0.0281(14) -0.0029(10) -0.0040(11) 0.0054(11) C15 0.0468(15) 0.0292(13) 0.0363(15) -0.0051(10) 0.0001(11) 0.0083(11) C16 0.0414(14) 0.0284(13) 0.0355(14) 0.0020(10) -0.0049(11) 0.0071(11) C17 0.0399(15) 0.0324(14) 0.0348(14) -0.0044(11) -0.0055(11) 0.0043(11) O24 0.0923(14) 0.0455(11) 0.0291(10) -0.0023(8) -0.0075(9) 0.0199(10) O27A 0.0721(12) 0.0365(10) 0.0343(10) 0.0040(8) -0.0086(8) 0.0091(9) O27B 0.0821(13) 0.0343(10) 0.0330(10) -0.0041(8) -0.0055(8) 0.0085(9) C21 0.0333(13) 0.0295(12) 0.0310(13) -0.0019(10) -0.0025(10) -0.0006(10) C22 0.0392(14) 0.0272(12) 0.0351(14) -0.0063(10) -0.0019(11) 0.0041(10) C23 0.0437(15) 0.0279(13) 0.0360(15) 0.0013(11) -0.0089(11) 0.0064(11) C24 0.0428(15) 0.0305(13) 0.0321(14) -0.0009(10) -0.0067(11) 0.0026(11) C25 0.0551(16) 0.0305(13) 0.0369(15) -0.0072(11) 0.0003(12) 0.0102(12) C26 0.0518(16) 0.0284(13) 0.0322(14) 0.0012(10) -0.0051(11) 0.0090(11) C27 0.0401(15) 0.0350(14) 0.0350(14) -0.0014(11) -0.0033(11) 0.0003(11) O91 0.0853(14) 0.0455(11) 0.0474(11) -0.0098(8) 0.0081(9) -0.0015(10) O93 0.0595(11) 0.0398(10) 0.0481(11) -0.0073(8) -0.0047(8) 0.0035(8) O90 0.0869(14) 0.0453(10) 0.0464(11) 0.0046(8) -0.0224(9) -0.0031(10) O92 0.0592(11) 0.0393(10) 0.0475(11) 0.0012(8) -0.0070(8) 0.0051(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 N31 C31 1.320(3) . ? N31 H31B 0.8600 . ? N31 H31A 0.8599 . ? N32 C31 1.317(3) . ? N32 C33 1.353(3) . ? N33 C33 1.311(3) . ? N33 H34B 0.8600 . ? N33 H33B 0.8601 . ? N34 C35 1.325(3) . ? N34 C33 1.355(3) . ? N35 C35 1.317(2) . ? N35 H45A 0.8601 . ? N35 H45B 0.8600 . ? N36 C35 1.359(3) . ? N36 C31 1.363(3) . ? N36 H36 1.0469 . ? N41 C41 1.316(3) . ? N41 H41B 0.8601 . ? N41 H41A 0.8599 . ? N42 C41 1.321(3) . ? N42 C43 1.358(3) . ? N43 C43 1.313(3) . ? N43 H43B 0.8601 . ? N43 H43A 0.8601 . ? N44 C45 1.324(3) . ? N44 C43 1.353(3) . ? N45 C45 1.314(3) . ? N45 H26A 0.8601 . ? N45 H26B 0.8600 . ? N46 C41 1.360(3) . ? N46 C45 1.366(3) . ? N46 H46 1.0203 . ? O14 C14 1.358(2) . ? O14 H14 0.8973 . ? O17A C17 1.261(3) . ? O17B C17 1.265(2) . ? C11 C12 1.387(3) . ? C11 C16 1.392(3) . ? C11 C17 1.488(3) . ? C12 C13 1.372(3) . ? C12 H12 0.9300 . ? C13 C14 1.383(3) . ? C13 H13 0.9300 . ? C14 C15 1.382(3) . ? C15 C16 1.368(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? O24 C24 1.357(2) . ? O24 H24 0.8743 . ? O27A C27 1.273(2) . ? O27B C27 1.256(3) . ? C21 C22 1.391(3) . ? C21 C26 1.395(3) . ? C21 C27 1.479(3) . ? C22 C23 1.366(3) . ? C22 H22 0.9300 . ? C23 C24 1.381(3) . ? C23 H23 0.9300 . ? C24 C25 1.385(3) . ? C25 C26 1.363(3) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? O91 H91A 0.9548 . ? O91 H91B 0.7620 . ? O93 H93B 0.8408 . ? O93 H93A 0.8678 . ? O90 H92A 0.8459 . ? O90 H90A 0.8811 . ? O92 H92B 0.8980 . ? O92 H0AA 0.8507 . ? 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 C31 N31 H31B 120.1 . . ? C31 N31 H31A 119.9 . . ? H31B N31 H31A 120.0 . . ? C31 N32 C33 115.76(18) . . ? C33 N33 H34B 120.0 . . ? C33 N33 H33B 120.0 . . ? H34B N33 H33B 120.0 . . ? C35 N34 C33 115.31(18) . . ? C35 N35 H45A 120.0 . . ? C35 N35 H45B 120.0 . . ? H45A N35 H45B 120.0 . . ? C35 N36 C31 118.82(18) . . ? C35 N36 H36 116.8 . . ? C31 N36 H36 124.2 . . ? N32 C31 N31 121.7(2) . . ? N32 C31 N36 122.01(19) . . ? N31 C31 N36 116.3(2) . . ? N33 C33 N32 116.77(19) . . ? N33 C33 N34 117.29(19) . . ? N32 C33 N34 125.95(19) . . ? N35 C35 N34 120.90(19) . . ? N35 C35 N36 117.0(2) . . ? N34 C35 N36 122.15(19) . . ? C41 N41 H41B 120.0 . . ? C41 N41 H41A 120.0 . . ? H41B N41 H41A 120.0 . . ? C41 N42 C43 115.49(18) . . ? C43 N43 H43B 120.1 . . ? C43 N43 H43A 120.0 . . ? H43B N43 H43A 120.0 . . ? C45 N44 C43 115.91(18) . . ? C45 N45 H26A 119.9 . . ? C45 N45 H26B 120.1 . . ? H26A N45 H26B 120.0 . . ? C41 N46 C45 118.97(18) . . ? C41 N46 H46 116.9 . . ? C45 N46 H46 124.1 . . ? N41 C41 N42 121.0(2) . . ? N41 C41 N46 116.8(2) . . ? N42 C41 N46 122.21(19) . . ? N43 C43 N44 116.70(19) . . ? N43 C43 N42 117.51(19) . . ? N44 C43 N42 125.78(19) . . ? N45 C45 N44 121.4(2) . . ? N45 C45 N46 116.9(2) . . ? N44 C45 N46 121.63(19) . . ? C14 O14 H14 108.9 . . ? C12 C11 C16 117.8(2) . . ? C12 C11 C17 120.20(19) . . ? C16 C11 C17 122.05(19) . . ? C13 C12 C11 121.4(2) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C12 C13 C14 120.0(2) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? O14 C14 C15 123.2(2) . . ? O14 C14 C13 117.3(2) . . ? C15 C14 C13 119.5(2) . . ? C16 C15 C14 120.2(2) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C11 121.2(2) . . ? C15 C16 H16 119.4 . . ? C11 C16 H16 119.4 . . ? O17A C17 O17B 122.8(2) . . ? O17A C17 C11 118.66(19) . . ? O17B C17 C11 118.5(2) . . ? C24 O24 H24 114.5 . . ? C22 C21 C26 117.6(2) . . ? C22 C21 C27 121.94(19) . . ? C26 C21 C27 120.4(2) . . ? C23 C22 C21 121.3(2) . . ? C23 C22 H22 119.3 . . ? C21 C22 H22 119.3 . . ? C22 C23 C24 120.2(2) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? O24 C24 C23 123.2(2) . . ? O24 C24 C25 117.53(19) . . ? C23 C24 C25 119.3(2) . . ? C26 C25 C24 120.3(2) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C25 C26 C21 121.2(2) . . ? C25 C26 H26 119.4 . . ? C21 C26 H26 119.4 . . ? O27B C27 O27A 122.3(2) . . ? O27B C27 C21 119.1(2) . . ? O27A C27 C21 118.60(19) . . ? H91A O91 H91B 107.7 . . ? H93B O93 H93A 109.7 . . ? H92A O90 H90A 99.8 . . ? H92B O92 H0AA 107.1 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.23 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.195 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.055