# 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_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Hai-Xia Zhao' _publ_contact_author_email hxzhao@xmu.edu.cn _publ_section_title ; The Influence of Water on Dielectric Property in Cocrystal Compound of [orotic acid][melamine];H2O ; loop_ _publ_author_name 'Hao-Ran Xu' 'Yan-Ping Ren' 'Qian-Chong Zhang' 'Hai-Xia Zhao' ; La-Sheng Long ; 'Rong-Bin Huang' 'Lan-Sun Zheng' # Attachment '- C1DT10423C_ccdc_813900_813902_cif.txt' data_1-200k #TrackingRef '- C1DT10423C_ccdc_813900_813902_cif.txt' _database_code_depnum_ccdc_archive 'CCDC 813900' #TrackingRef 'p.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H12 N8 O5' _chemical_formula_weight 300.26 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1689(6) _cell_length_b 8.3465(6) _cell_length_c 9.7857(8) _cell_angle_alpha 113.114(7) _cell_angle_beta 98.197(7) _cell_angle_gamma 99.316(6) _cell_volume 589.73(8) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 2513 _cell_measurement_theta_min 3.0590 _cell_measurement_theta_max 28.7614 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.691 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.142 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9324 _exptl_absorpt_correction_T_max 0.9722 _exptl_absorpt_process_details 'CrysAlis RED' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'CrysAlis CCD, Oxford Diffraction Ltd.' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4256 _diffrn_reflns_av_R_equivalents 0.0164 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2306 _reflns_number_gt 1860 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD' _computing_cell_refinement 'CrysAlis RED' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0658P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2306 _refine_ls_number_parameters 234 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.1073 _refine_ls_wR_factor_gt 0.1036 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7662(2) 1.5439(2) 0.55587(19) 0.0176(4) Uani 1 1 d . . . C2 C 0.9316(2) 1.8052(2) 0.76374(19) 0.0177(4) Uani 1 1 d . . . C3 C 0.7128(2) 1.6233(2) 0.7908(2) 0.0186(4) Uani 1 1 d . . . N1 N 0.67224(18) 1.50443(18) 0.64284(17) 0.0212(3) Uani 1 1 d . . . N2 N 0.84044(17) 1.77532(18) 0.85716(16) 0.0196(3) Uani 1 1 d . . . N3 N 0.89537(18) 1.69412(18) 0.61291(16) 0.0205(3) Uani 1 1 d . . . N4 N 0.74055(19) 1.4384(2) 0.40979(18) 0.0233(3) Uani 1 1 d . . . N5 N 1.0618(2) 1.9455(2) 0.8130(2) 0.0246(4) Uani 1 1 d . . . N6 N 0.6187(2) 1.5880(2) 0.87932(19) 0.0239(4) Uani 1 1 d . . . O1 O 0.22112(16) 0.95126(16) 0.55804(14) 0.0294(3) Uani 1 1 d . . . O2 O 0.01614(15) 0.72271(16) 0.38482(14) 0.0271(3) Uani 1 1 d . . . H2A H -0.0174 0.7192 0.4621 0.032 Uiso 1 1 d R . . O3 O 0.53464(15) 1.10462(15) 0.19035(14) 0.0249(3) Uani 1 1 d . . . O4 O 0.14228(15) 0.58174(15) -0.09814(13) 0.0238(3) Uani 1 1 d . . . C4 C 0.4193(2) 0.9869(2) 0.18698(19) 0.0189(4) Uani 1 1 d . . . C5 C 0.2061(2) 0.7049(2) 0.02749(19) 0.0178(4) Uani 1 1 d . . . C6 C 0.3587(2) 0.9855(2) 0.3176(2) 0.0200(4) Uani 1 1 d . . . C7 C 0.2273(2) 0.8526(2) 0.29749(19) 0.0185(4) Uani 1 1 d . . . C8 C 0.1493(2) 0.8431(2) 0.42583(19) 0.0188(4) Uani 1 1 d . . . N7 N 0.15267(18) 0.71743(18) 0.15656(16) 0.0187(3) Uani 1 1 d . . . N8 N 0.33866(18) 0.84366(18) 0.05007(17) 0.0197(3) Uani 1 1 d . . . O1W O 0.32270(17) 1.28660(19) 0.78997(16) 0.0278(3) Uani 1 1 d . . . H6 H 0.405(2) 1.074(2) 0.412(2) 0.020(5) Uiso 1 1 d . . . H8 H 0.374(3) 0.844(3) -0.031(3) 0.043(6) Uiso 1 1 d . . . H7 H 0.072(3) 0.635(3) 0.149(2) 0.029(5) Uiso 1 1 d . . . H4A H 0.806(3) 1.469(3) 0.347(3) 0.038(6) Uiso 1 1 d . . . H4B H 0.662(3) 1.337(3) 0.371(3) 0.036(6) Uiso 1 1 d . . . H5A H 1.086(2) 2.018(3) 0.906(3) 0.027(5) Uiso 1 1 d . . . H5B H 1.114(3) 1.962(3) 0.749(3) 0.044(7) Uiso 1 1 d . . . H6A H 0.529(3) 1.484(3) 0.832(3) 0.043(6) Uiso 1 1 d . . . H6B H 0.645(3) 1.653(3) 0.975(3) 0.032(6) Uiso 1 1 d . . . H1WA H 0.240(3) 1.334(3) 0.771(3) 0.064(8) Uiso 1 1 d . . . H1WB H 0.309(4) 1.178(4) 0.710(4) 0.083(10) 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 C1 0.0181(8) 0.0192(8) 0.0159(9) 0.0081(7) 0.0048(7) 0.0032(7) C2 0.0185(8) 0.0179(8) 0.0154(9) 0.0059(7) 0.0037(7) 0.0039(7) C3 0.0178(8) 0.0193(8) 0.0201(9) 0.0092(7) 0.0056(7) 0.0050(7) N1 0.0219(8) 0.0207(7) 0.0178(8) 0.0062(6) 0.0058(6) 0.0007(6) N2 0.0194(7) 0.0209(7) 0.0162(8) 0.0061(6) 0.0058(6) 0.0016(6) N3 0.0212(7) 0.0200(7) 0.0163(8) 0.0051(6) 0.0049(6) 0.0004(6) N4 0.0248(8) 0.0219(8) 0.0171(8) 0.0053(7) 0.0063(6) -0.0043(6) N5 0.0251(8) 0.0246(8) 0.0158(9) 0.0033(7) 0.0064(7) -0.0037(6) N6 0.0273(8) 0.0238(8) 0.0176(9) 0.0072(7) 0.0090(7) -0.0011(7) O1 0.0339(7) 0.0281(7) 0.0158(7) 0.0036(6) 0.0061(6) -0.0056(6) O2 0.0275(7) 0.0321(7) 0.0166(7) 0.0088(6) 0.0092(5) -0.0057(5) O3 0.0257(7) 0.0232(6) 0.0188(7) 0.0071(5) 0.0041(5) -0.0072(5) O4 0.0278(7) 0.0203(6) 0.0159(7) 0.0030(5) 0.0057(5) -0.0018(5) C4 0.0182(8) 0.0191(8) 0.0171(9) 0.0062(7) 0.0032(7) 0.0031(7) C5 0.0196(8) 0.0156(8) 0.0180(9) 0.0072(7) 0.0052(7) 0.0030(7) C6 0.0225(9) 0.0194(8) 0.0133(9) 0.0041(8) 0.0026(7) 0.0009(7) C7 0.0209(9) 0.0194(8) 0.0164(9) 0.0081(7) 0.0050(7) 0.0061(7) C8 0.0211(9) 0.0184(8) 0.0156(9) 0.0063(7) 0.0056(7) 0.0028(7) N7 0.0196(8) 0.0163(7) 0.0175(8) 0.0063(6) 0.0057(6) -0.0018(6) N8 0.0213(8) 0.0220(7) 0.0143(8) 0.0074(6) 0.0062(6) 0.0001(6) O1W 0.0294(8) 0.0258(7) 0.0225(7) 0.0064(6) 0.0047(6) 0.0029(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N4 1.315(2) . ? C1 N1 1.322(2) . ? C1 N3 1.361(2) . ? C2 N5 1.320(2) . ? C2 N2 1.329(2) . ? C2 N3 1.356(2) . ? C3 N6 1.321(2) . ? C3 N1 1.349(2) . ? C3 N2 1.361(2) . ? O1 C8 1.236(2) . ? O2 C8 1.248(2) . ? O3 C4 1.233(2) . ? O4 C5 1.221(2) . ? C4 N8 1.376(2) . ? C4 C6 1.439(2) . ? C5 N7 1.366(2) . ? C5 N8 1.374(2) . ? C6 C7 1.343(2) . ? C7 N7 1.365(2) . ? C7 C8 1.510(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 C1 N1 121.50(15) . . ? N4 C1 N3 116.63(15) . . ? N1 C1 N3 121.87(16) . . ? N5 C2 N2 121.63(16) . . ? N5 C2 N3 116.47(15) . . ? N2 C2 N3 121.90(15) . . ? N6 C3 N1 116.49(15) . . ? N6 C3 N2 117.14(16) . . ? N1 C3 N2 126.37(15) . . ? C1 N1 C3 115.47(14) . . ? C2 N2 C3 114.97(15) . . ? C2 N3 C1 119.37(14) . . ? O3 C4 N8 119.57(15) . . ? O3 C4 C6 125.01(16) . . ? N8 C4 C6 115.43(14) . . ? O4 C5 N7 123.43(14) . . ? O4 C5 N8 122.22(15) . . ? N7 C5 N8 114.35(15) . . ? C7 C6 C4 119.08(16) . . ? C6 C7 N7 121.44(15) . . ? C6 C7 C8 123.24(16) . . ? N7 C7 C8 115.30(14) . . ? O1 C8 O2 126.77(15) . . ? O1 C8 C7 118.37(14) . . ? O2 C8 C7 114.86(15) . . ? C7 N7 C5 123.29(14) . . ? C5 N8 C4 126.35(14) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2A N3 0.85 1.80 2.6424(18) 174.6 1_445 O2 H2A N4 0.85 2.63 3.1051(19) 116.4 1_445 N8 H8 O3 0.88(2) 1.99(2) 2.8531(18) 169(2) 2_675 N7 H7 O4 0.84(2) 2.15(2) 2.9843(18) 172(2) 2_565 N4 H4A O2 0.95(2) 2.37(2) 3.1051(19) 134.4(18) 1_665 N4 H4A O4 0.95(2) 2.42(2) 3.2752(18) 150.8(18) 2_675 N4 H4B O3 0.88(2) 2.02(2) 2.821(2) 150(2) . N5 H5A N2 0.84(2) 2.20(2) 3.040(2) 175.6(18) 2_797 N5 H5B O1 0.85(2) 2.15(3) 2.987(2) 169(2) 1_665 N6 H6A O1W 0.94(2) 2.02(2) 2.939(2) 164(2) . N6 H6B O1W 0.85(2) 2.12(2) 2.921(2) 157.2(18) 2_687 O1W H1WA O2 0.87(3) 2.27(3) 3.0115(19) 144(2) 2_576 O1W H1WA O4 0.87(3) 2.30(3) 2.9928(19) 136(2) 1_566 O1W H1WB O1 0.91(3) 1.83(3) 2.7197(19) 164(3) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.640 _refine_diff_density_min -0.576 _refine_diff_density_rms 0.052 data_1-265k #TrackingRef '- C1DT10423C_ccdc_813900_813902_cif.txt' _database_code_depnum_ccdc_archive 'CCDC 813901' #TrackingRef 'p.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H12 N8 O5' _chemical_formula_weight 300.26 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1960(6) _cell_length_b 8.3777(7) _cell_length_c 9.7987(8) _cell_angle_alpha 113.233(7) _cell_angle_beta 97.935(6) _cell_angle_gamma 99.632(6) _cell_volume 593.88(8) _cell_formula_units_Z 2 _cell_measurement_temperature 265(2) _cell_measurement_reflns_used 2397 _cell_measurement_theta_min 3.0566 _cell_measurement_theta_max 28.7567 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.679 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.141 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9328 _exptl_absorpt_correction_T_max 0.9723 _exptl_absorpt_process_details 'CrysAlis RED' _exptl_special_details ; ? ; _diffrn_ambient_temperature 265(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 'CrysAlis CCD, Oxford Diffraction Ltd.' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4246 _diffrn_reflns_av_R_equivalents 0.0163 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2326 _reflns_number_gt 1856 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD' _computing_cell_refinement 'CrysAlis RED' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0705P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2326 _refine_ls_number_parameters 234 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1117 _refine_ls_wR_factor_gt 0.1077 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7668(2) 1.5445(2) 0.55576(19) 0.0222(4) Uani 1 1 d . . . C2 C 0.9320(2) 1.8052(2) 0.76372(19) 0.0227(4) Uani 1 1 d . . . C3 C 0.7132(2) 1.6233(2) 0.7905(2) 0.0234(4) Uani 1 1 d . . . N1 N 0.67287(19) 1.50499(19) 0.64248(17) 0.0268(4) Uani 1 1 d . . . N2 N 0.84075(18) 1.77530(18) 0.85674(16) 0.0247(3) Uani 1 1 d . . . N3 N 0.89564(18) 1.69437(19) 0.61284(16) 0.0253(3) Uani 1 1 d . . . N4 N 0.7406(2) 1.4393(2) 0.40958(18) 0.0302(4) Uani 1 1 d . . . N5 N 1.0620(2) 1.9454(2) 0.8130(2) 0.0312(4) Uani 1 1 d . . . N6 N 0.6192(2) 1.5881(2) 0.8790(2) 0.0305(4) Uani 1 1 d . . . O1 O 0.22112(18) 0.95158(17) 0.55781(14) 0.0377(4) Uani 1 1 d . . . O2 O 0.01707(16) 0.72299(17) 0.38521(14) 0.0348(3) Uani 1 1 d . . . H2A H -0.0165 0.7195 0.4625 0.042 Uiso 1 1 d R . . O3 O 0.53438(16) 1.10458(16) 0.19045(14) 0.0318(3) Uani 1 1 d . . . O4 O 0.14263(16) 0.58240(15) -0.09751(14) 0.0302(3) Uani 1 1 d . . . C4 C 0.4194(2) 0.9873(2) 0.18683(19) 0.0238(4) Uani 1 1 d . . . C5 C 0.2063(2) 0.7054(2) 0.02767(19) 0.0226(4) Uani 1 1 d . . . C6 C 0.3584(2) 0.9858(2) 0.3173(2) 0.0250(4) Uani 1 1 d . . . C7 C 0.2275(2) 0.8534(2) 0.29756(19) 0.0229(4) Uani 1 1 d . . . C8 C 0.1492(2) 0.8435(2) 0.42573(19) 0.0246(4) Uani 1 1 d . . . N7 N 0.15290(19) 0.71798(19) 0.15680(16) 0.0234(3) Uani 1 1 d . . . N8 N 0.33860(18) 0.84395(19) 0.05055(17) 0.0245(3) Uani 1 1 d . . . O1W O 0.32260(19) 1.2869(2) 0.78986(17) 0.0355(4) Uani 1 1 d . . . H6 H 0.402(2) 1.073(2) 0.411(2) 0.026(5) Uiso 1 1 d . . . H8 H 0.372(3) 0.842(3) -0.030(3) 0.043(6) Uiso 1 1 d . . . H7 H 0.072(3) 0.634(3) 0.147(2) 0.032(5) Uiso 1 1 d . . . H4A H 0.808(3) 1.470(3) 0.345(3) 0.046(6) Uiso 1 1 d . . . H4B H 0.660(3) 1.340(3) 0.371(2) 0.036(6) Uiso 1 1 d . . . H5A H 1.084(3) 2.014(3) 0.904(3) 0.037(6) Uiso 1 1 d . . . H5B H 1.114(3) 1.959(3) 0.750(3) 0.049(7) Uiso 1 1 d . . . H6A H 0.532(3) 1.482(3) 0.833(3) 0.045(6) Uiso 1 1 d . . . H6B H 0.649(3) 1.653(3) 0.974(3) 0.042(6) Uiso 1 1 d . . . H1WA H 0.244(4) 1.335(4) 0.774(4) 0.080(10) Uiso 1 1 d . . . H1WB H 0.309(4) 1.184(4) 0.714(4) 0.081(10) 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 C1 0.0231(9) 0.0234(8) 0.0194(9) 0.0089(7) 0.0061(7) 0.0031(7) C2 0.0237(9) 0.0233(8) 0.0189(9) 0.0071(7) 0.0055(7) 0.0044(7) C3 0.0227(9) 0.0246(8) 0.0227(9) 0.0101(7) 0.0062(7) 0.0050(7) N1 0.0269(8) 0.0269(8) 0.0222(8) 0.0081(6) 0.0076(6) -0.0004(6) N2 0.0252(8) 0.0261(8) 0.0200(8) 0.0078(6) 0.0074(6) 0.0021(6) N3 0.0267(8) 0.0249(7) 0.0187(7) 0.0061(6) 0.0060(6) -0.0003(6) N4 0.0328(9) 0.0276(8) 0.0210(8) 0.0055(7) 0.0076(7) -0.0056(7) N5 0.0315(9) 0.0307(9) 0.0208(9) 0.0046(8) 0.0081(7) -0.0053(7) N6 0.0341(9) 0.0312(9) 0.0216(9) 0.0091(7) 0.0110(7) -0.0018(7) O1 0.0436(8) 0.0374(8) 0.0185(7) 0.0046(6) 0.0083(6) -0.0073(6) O2 0.0356(8) 0.0409(7) 0.0199(7) 0.0102(6) 0.0116(6) -0.0084(6) O3 0.0327(7) 0.0300(7) 0.0235(7) 0.0094(6) 0.0054(6) -0.0097(6) O4 0.0361(7) 0.0251(6) 0.0193(7) 0.0030(6) 0.0072(6) -0.0032(6) C4 0.0236(9) 0.0238(8) 0.0209(9) 0.0085(7) 0.0039(7) 0.0016(7) C5 0.0243(9) 0.0212(8) 0.0216(9) 0.0086(7) 0.0070(7) 0.0032(7) C6 0.0276(10) 0.0244(9) 0.0168(9) 0.0056(8) 0.0033(7) 0.0002(7) C7 0.0258(9) 0.0235(9) 0.0195(9) 0.0088(7) 0.0064(7) 0.0064(7) C8 0.0281(10) 0.0244(9) 0.0196(9) 0.0080(7) 0.0085(7) 0.0032(7) N7 0.0252(8) 0.0215(7) 0.0195(8) 0.0069(6) 0.0078(6) -0.0020(6) N8 0.0272(8) 0.0273(8) 0.0168(8) 0.0090(6) 0.0079(6) -0.0003(6) O1W 0.0383(9) 0.0318(8) 0.0287(8) 0.0078(7) 0.0058(6) 0.0031(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N4 1.315(2) . ? C1 N1 1.319(2) . ? C1 N3 1.358(2) . ? C2 N5 1.319(2) . ? C2 N2 1.326(2) . ? C2 N3 1.356(2) . ? C3 N6 1.320(2) . ? C3 N1 1.349(2) . ? C3 N2 1.361(2) . ? O1 C8 1.236(2) . ? O2 C8 1.245(2) . ? O3 C4 1.228(2) . ? O4 C5 1.219(2) . ? C4 N8 1.374(2) . ? C4 C6 1.438(2) . ? C5 N7 1.366(2) . ? C5 N8 1.371(2) . ? C6 C7 1.340(2) . ? C7 N7 1.365(2) . ? C7 C8 1.511(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 C1 N1 121.40(16) . . ? N4 C1 N3 116.75(15) . . ? N1 C1 N3 121.84(16) . . ? N5 C2 N2 121.68(16) . . ? N5 C2 N3 116.52(16) . . ? N2 C2 N3 121.80(15) . . ? N6 C3 N1 116.68(16) . . ? N6 C3 N2 117.11(16) . . ? N1 C3 N2 126.21(15) . . ? C1 N1 C3 115.59(15) . . ? C2 N2 C3 115.07(15) . . ? C2 N3 C1 119.44(14) . . ? O3 C4 N8 119.91(15) . . ? O3 C4 C6 124.96(16) . . ? N8 C4 C6 115.13(15) . . ? O4 C5 N7 123.39(15) . . ? O4 C5 N8 122.44(15) . . ? N7 C5 N8 114.18(15) . . ? C7 C6 C4 119.27(16) . . ? C6 C7 N7 121.39(15) . . ? C6 C7 C8 123.47(16) . . ? N7 C7 C8 115.12(14) . . ? O1 C8 O2 126.70(15) . . ? O1 C8 C7 118.25(15) . . ? O2 C8 C7 115.05(15) . . ? C7 N7 C5 123.25(15) . . ? C5 N8 C4 126.72(14) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2A N3 0.85 1.79 2.6415(18) 174.4 1_445 O2 H2A N4 0.85 2.63 3.104(2) 116.3 1_445 N8 H8 O3 0.86(2) 2.01(2) 2.8598(19) 167(2) 2_675 N7 H7 O4 0.85(2) 2.15(2) 2.9925(19) 174(2) 2_565 N4 H4A O2 0.98(2) 2.35(2) 3.104(2) 133.6(18) 1_665 N4 H4A O4 0.98(2) 2.39(2) 3.2753(19) 150.5(18) 2_675 N4 H4B O3 0.88(2) 2.04(2) 2.827(2) 149.1(19) . N5 H5A N2 0.82(2) 2.23(3) 3.045(2) 172.9(19) 2_797 N5 H5B O1 0.83(3) 2.17(3) 2.989(2) 170(2) 1_665 N6 H6A O1W 0.94(2) 2.03(2) 2.943(2) 164(2) . N6 H6B O1W 0.85(2) 2.13(2) 2.929(2) 156(2) 2_687 O1W H1WA O2 0.84(3) 2.32(3) 3.032(2) 143(3) 2_576 O1W H1WA O4 0.84(3) 2.32(3) 3.006(2) 139(3) 1_566 O1W H1WB O1 0.86(3) 1.88(3) 2.722(2) 165(3) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.584 _refine_diff_density_min -0.508 _refine_diff_density_rms 0.051 data_1-298k #TrackingRef '- C1DT10423C_ccdc_813900_813902_cif.txt' _database_code_depnum_ccdc_archive 'CCDC 813902' #TrackingRef 'p.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H12 N8 O5' _chemical_formula_weight 300.26 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2133(6) _cell_length_b 8.3969(7) _cell_length_c 9.8069(8) _cell_angle_alpha 113.304(8) _cell_angle_beta 97.788(7) _cell_angle_gamma 99.804(7) _cell_volume 596.52(8) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2457 _cell_measurement_theta_min 3.0547 _cell_measurement_theta_max 28.7506 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.672 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.140 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9331 _exptl_absorpt_correction_T_max 0.9725 _exptl_absorpt_process_details 'CrysAlis RED' _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 'CrysAlis CCD, Oxford Diffraction Ltd.' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4270 _diffrn_reflns_av_R_equivalents 0.0159 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2338 _reflns_number_gt 1856 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD' _computing_cell_refinement 'CrysAlis RED' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2338 _refine_ls_number_parameters 234 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0490 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.1114 _refine_ls_wR_factor_gt 0.1074 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7665(2) 1.5447(2) 0.55574(19) 0.0248(4) Uani 1 1 d . . . C2 C 0.9321(2) 1.8053(2) 0.76367(19) 0.0252(4) Uani 1 1 d . . . C3 C 0.7136(2) 1.6237(2) 0.79045(19) 0.0259(4) Uani 1 1 d . . . N1 N 0.67308(19) 1.50561(19) 0.64270(17) 0.0301(4) Uani 1 1 d . . . N2 N 0.84113(18) 1.77550(18) 0.85669(16) 0.0271(3) Uani 1 1 d . . . N3 N 0.89601(18) 1.69471(19) 0.61294(16) 0.0284(3) Uani 1 1 d . . . N4 N 0.7405(2) 1.4396(2) 0.40961(18) 0.0339(4) Uani 1 1 d . . . N5 N 1.0617(2) 1.9451(2) 0.8126(2) 0.0351(4) Uani 1 1 d . . . N6 N 0.6197(2) 1.5883(2) 0.8790(2) 0.0344(4) Uani 1 1 d . . . O1 O 0.22088(18) 0.95184(17) 0.55778(14) 0.0424(4) Uani 1 1 d . . . O2 O 0.01779(16) 0.72276(17) 0.38524(14) 0.0390(3) Uani 1 1 d . . . H2A H -0.0158 0.7192 0.4625 0.047 Uiso 1 1 d R . . O3 O 0.53414(16) 1.10438(16) 0.19044(14) 0.0360(3) Uani 1 1 d . . . O4 O 0.14272(16) 0.58265(15) -0.09719(13) 0.0337(3) Uani 1 1 d . . . C4 C 0.4193(2) 0.9872(2) 0.18711(19) 0.0261(4) Uani 1 1 d . . . C5 C 0.2065(2) 0.7058(2) 0.02791(19) 0.0249(4) Uani 1 1 d . . . C6 C 0.3583(2) 0.9860(2) 0.3174(2) 0.0274(4) Uani 1 1 d . . . C7 C 0.2276(2) 0.8535(2) 0.29762(18) 0.0246(4) Uani 1 1 d . . . C8 C 0.1495(2) 0.8436(2) 0.42591(19) 0.0276(4) Uani 1 1 d . . . N7 N 0.15318(19) 0.71816(19) 0.15698(16) 0.0263(3) Uani 1 1 d . . . N8 N 0.33849(18) 0.84402(19) 0.05065(17) 0.0275(3) Uani 1 1 d . . . O1W O 0.32240(19) 1.2871(2) 0.78985(17) 0.0403(4) Uani 1 1 d . . . H6 H 0.404(2) 1.073(2) 0.411(2) 0.031(5) Uiso 1 1 d . . . H8 H 0.370(3) 0.841(3) -0.031(3) 0.043(6) Uiso 1 1 d . . . H7 H 0.070(3) 0.635(3) 0.145(2) 0.038(6) Uiso 1 1 d . . . H4A H 0.806(3) 1.471(3) 0.343(3) 0.046(6) Uiso 1 1 d . . . H4B H 0.661(3) 1.337(3) 0.370(2) 0.043(6) Uiso 1 1 d . . . H5A H 1.086(3) 2.015(3) 0.905(3) 0.041(6) Uiso 1 1 d . . . H5B H 1.115(3) 1.962(3) 0.752(3) 0.045(6) Uiso 1 1 d . . . H6A H 0.533(3) 1.482(3) 0.833(3) 0.050(6) Uiso 1 1 d . . . H6B H 0.650(3) 1.650(3) 0.971(3) 0.050(7) Uiso 1 1 d . . . H1WA H 0.244(4) 1.336(4) 0.774(4) 0.091(10) Uiso 1 1 d . . . H1WB H 0.312(4) 1.182(4) 0.711(4) 0.085(10) 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 C1 0.0259(9) 0.0267(8) 0.0203(8) 0.0091(7) 0.0071(7) 0.0035(7) C2 0.0264(9) 0.0258(8) 0.0210(8) 0.0082(7) 0.0062(7) 0.0041(7) C3 0.0258(9) 0.0282(8) 0.0236(9) 0.0113(7) 0.0067(7) 0.0048(7) N1 0.0305(8) 0.0306(8) 0.0244(8) 0.0093(6) 0.0091(6) -0.0009(6) N2 0.0280(8) 0.0288(7) 0.0215(8) 0.0085(6) 0.0084(6) 0.0023(6) N3 0.0302(8) 0.0282(7) 0.0206(7) 0.0068(6) 0.0072(6) -0.0002(6) N4 0.0369(9) 0.0320(8) 0.0227(8) 0.0063(7) 0.0085(7) -0.0048(7) N5 0.0349(9) 0.0345(9) 0.0237(9) 0.0054(8) 0.0096(7) -0.0067(7) N6 0.0380(9) 0.0350(9) 0.0252(9) 0.0105(8) 0.0128(7) -0.0027(7) O1 0.0491(9) 0.0420(8) 0.0200(7) 0.0048(6) 0.0088(6) -0.0088(6) O2 0.0395(8) 0.0455(8) 0.0217(7) 0.0105(6) 0.0123(6) -0.0102(6) O3 0.0372(7) 0.0336(7) 0.0260(7) 0.0099(6) 0.0058(6) -0.0113(6) O4 0.0401(8) 0.0284(7) 0.0209(7) 0.0035(5) 0.0078(6) -0.0040(6) C4 0.0261(9) 0.0257(8) 0.0229(9) 0.0092(7) 0.0044(7) 0.0008(7) C5 0.0272(9) 0.0222(8) 0.0231(9) 0.0083(7) 0.0077(7) 0.0026(7) C6 0.0305(10) 0.0272(9) 0.0175(9) 0.0057(8) 0.0035(7) 0.0002(7) C7 0.0281(9) 0.0249(8) 0.0205(9) 0.0091(7) 0.0068(7) 0.0060(7) C8 0.0309(9) 0.0279(9) 0.0221(9) 0.0095(7) 0.0093(7) 0.0030(7) N7 0.0280(8) 0.0234(7) 0.0222(8) 0.0073(6) 0.0083(6) -0.0029(6) N8 0.0309(8) 0.0292(8) 0.0196(7) 0.0099(6) 0.0089(6) -0.0008(6) O1W 0.0426(9) 0.0362(8) 0.0324(8) 0.0086(7) 0.0065(6) 0.0027(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N4 1.315(2) . ? C1 N1 1.318(2) . ? C1 N3 1.362(2) . ? C2 N5 1.316(2) . ? C2 N2 1.325(2) . ? C2 N3 1.355(2) . ? C3 N6 1.320(2) . ? C3 N1 1.347(2) . ? C3 N2 1.360(2) . ? O1 C8 1.235(2) . ? O2 C8 1.244(2) . ? O3 C4 1.229(2) . ? O4 C5 1.219(2) . ? C4 N8 1.375(2) . ? C4 C6 1.437(2) . ? C5 N7 1.366(2) . ? C5 N8 1.369(2) . ? C6 C7 1.339(2) . ? C7 N7 1.365(2) . ? C7 C8 1.511(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 C1 N1 121.58(16) . . ? N4 C1 N3 116.69(15) . . ? N1 C1 N3 121.73(15) . . ? N5 C2 N2 121.70(16) . . ? N5 C2 N3 116.35(16) . . ? N2 C2 N3 121.94(15) . . ? N6 C3 N1 116.59(16) . . ? N6 C3 N2 117.12(16) . . ? N1 C3 N2 126.30(15) . . ? C1 N1 C3 115.66(14) . . ? C2 N2 C3 115.00(14) . . ? C2 N3 C1 119.33(14) . . ? O3 C4 N8 119.73(15) . . ? O3 C4 C6 125.03(16) . . ? N8 C4 C6 115.24(15) . . ? O4 C5 N7 123.26(15) . . ? O4 C5 N8 122.49(15) . . ? N7 C5 N8 114.24(15) . . ? C7 C6 C4 119.18(16) . . ? C6 C7 N7 121.45(15) . . ? C6 C7 C8 123.36(15) . . ? N7 C7 C8 115.17(14) . . ? O1 C8 O2 126.74(15) . . ? O1 C8 C7 118.35(15) . . ? O2 C8 C7 114.90(15) . . ? C7 N7 C5 123.22(14) . . ? C5 N8 C4 126.62(14) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2A N3 0.85 1.80 2.6427(18) 174.4 1_445 O2 H2A N4 0.85 2.63 3.106(2) 116.3 1_445 N8 H8 O3 0.87(2) 2.01(2) 2.8633(19) 166.4(19) 2_675 N7 H7 O4 0.85(2) 2.15(2) 2.9969(19) 175(2) 2_565 N4 H4A O2 0.98(2) 2.35(2) 3.106(2) 133.2(17) 1_665 N4 H4A O4 0.98(2) 2.39(2) 3.2782(19) 150.9(17) 2_675 N4 H4B O3 0.89(2) 2.02(2) 2.832(2) 150(2) . N5 H5A N2 0.83(2) 2.22(2) 3.050(2) 173.9(18) 2_797 N5 H5B O1 0.83(2) 2.17(2) 2.988(2) 168(2) 1_665 N6 H6A O1W 0.94(2) 2.03(2) 2.949(2) 163(2) . N6 H6B O1W 0.82(2) 2.16(3) 2.931(2) 158(2) 2_687 O1W H1WA O2 0.85(3) 2.33(3) 3.045(2) 142(3) 2_576 O1W H1WA O4 0.85(3) 2.32(3) 3.013(2) 139(3) 1_566 O1W H1WB O1 0.90(3) 1.86(3) 2.724(2) 162(3) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.577 _refine_diff_density_min -0.450 _refine_diff_density_rms 0.048