# Supplementary Material (ESI) for CrystEngComm # This journal is (c) 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 'Adam Pietraszko' _publ_contact_author_email A.Pietraszko@int.pan.wroc.pl loop_ _publ_author_name 'K. Pogorzelec-Glasera' 'A. Pietraszko' 'J. Baran' 'B. Hilczera' J.Maleckia 'M. Polomska' 'P. Lawniczak' #TrackingRef '- P21CC corrected.CIF' data_p21cc _database_code_depnum_ccdc_archive 'CCDC 807488' #TrackingRef '- P21CC corrected.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Bis_1H-1,2,4-Triazole_Succinic_Acid _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H12 N6 O4' _chemical_formula_weight 256.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P2(1)/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 5.3540(11) _cell_length_b 18.372(4) _cell_length_c 6.8327(14) _cell_angle_alpha 90.00 _cell_angle_beta 113.85(3) _cell_angle_gamma 90.00 _cell_volume 614.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'irregular cuboid' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 "'Xcalibur- Oxford Diffraction" _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5852 _diffrn_reflns_av_R_equivalents 0.0768 _diffrn_reflns_av_sigmaI/netI 0.0722 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 25.32 _reflns_number_total 1097 _reflns_number_gt 578 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CRYSALIS VER 170.33.42' _computing_cell_refinement 'CRYSALIS VER 170.33.42' _computing_data_reduction 'CRYSALIS VER 170.33.42' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.1' _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^)+(0.0200P)^2^+0.0200P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0124(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1097 _refine_ls_number_parameters 108 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1311 _refine_ls_R_factor_gt 0.0566 _refine_ls_wR_factor_ref 0.0886 _refine_ls_wR_factor_gt 0.0782 _refine_ls_goodness_of_fit_ref 1.179 _refine_ls_restrained_S_all 1.179 _refine_ls_shift/su_max 0.171 _refine_ls_shift/su_mean 0.030 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.07950(15) 0.46668(4) 0.78915(13) 0.0655(3) Uani 1 1 d . . . O2 O 0.79552(16) 0.39051(4) 0.55199(12) 0.0692(3) Uani 1 1 d . . . C1 C 0.8409(2) 0.44894(6) 0.64062(17) 0.0464(4) Uani 1 1 d . . . C2 C 0.6342(2) 0.50881(6) 0.59169(18) 0.0506(4) Uani 1 1 d . . . N1 N 0.62587(19) 0.24592(5) 0.46956(13) 0.0569(4) Uani 1 1 d . . . N2 N 0.83274(18) 0.19958(5) 0.57407(15) 0.0602(4) Uani 1 1 d . . . C3 C 0.7074(2) 0.13663(6) 0.53434(18) 0.0571(4) Uani 1 1 d . . . N4 N 0.43703(17) 0.14002(5) 0.41153(14) 0.0554(3) Uani 1 1 d . . . C5 C 0.3960(2) 0.21029(6) 0.37466(19) 0.0572(5) Uani 1 1 d . . . HO1 H 1.190(2) 0.4237(6) 0.8181(16) 0.099(4) Uiso 1 1 d . . . H21 H 0.6050(18) 0.5200(5) 0.7208(13) 0.052(3) Uiso 1 1 d . . . H22 H 0.7054(18) 0.5494(5) 0.5633(14) 0.062(3) Uiso 1 1 d . . . H1 H 0.658(2) 0.2917(6) 0.4803(15) 0.080(4) Uiso 1 1 d . . . H3 H 0.8147(19) 0.0871(6) 0.5959(14) 0.072(3) Uiso 1 1 d . . . H5 H 0.216(2) 0.2354(6) 0.2883(14) 0.078(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0413(4) 0.0435(4) 0.0877(6) -0.0079(4) 0.0013(4) 0.0074(4) O2 0.0626(5) 0.0403(4) 0.0850(5) -0.0119(4) 0.0095(4) 0.0064(4) C1 0.0372(6) 0.0350(6) 0.0614(7) 0.0006(5) 0.0142(5) 0.0002(5) C2 0.0404(7) 0.0364(6) 0.0669(7) -0.0043(6) 0.0132(5) 0.0044(6) N1 0.0501(6) 0.0344(5) 0.0747(6) -0.0028(5) 0.0133(5) -0.0046(5) N2 0.0371(5) 0.0484(6) 0.0788(7) -0.0050(5) 0.0066(5) -0.0016(5) C3 0.0439(7) 0.0436(7) 0.0702(8) -0.0005(6) 0.0090(6) 0.0023(6) N4 0.0358(5) 0.0441(5) 0.0713(6) -0.0011(5) 0.0062(5) -0.0078(5) C5 0.0417(7) 0.0504(7) 0.0659(8) 0.0026(6) 0.0077(6) 0.0021(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.3112(12) . ? O1 HO1 0.960(11) . ? O2 C1 1.2080(13) . ? C1 C2 1.4992(15) . ? C2 C2 1.5112(19) 3_666 ? C2 H21 0.978(10) . ? C2 H22 0.893(10) . ? N1 C5 1.3107(14) . ? N1 N2 1.3499(12) . ? N1 H1 0.855(11) . ? N2 C3 1.3093(15) . ? C3 N4 1.3494(14) . ? C3 H3 1.067(10) . ? N4 C5 1.3166(14) . ? C5 H5 1.015(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 HO1 106.4(6) . . ? O2 C1 O1 122.99(10) . . ? O2 C1 C2 124.02(9) . . ? O1 C1 C2 112.99(9) . . ? C1 C2 C2 113.36(11) . 3_666 ? C1 C2 H21 109.0(5) . . ? C2 C2 H21 110.4(5) 3_666 . ? C1 C2 H22 108.6(6) . . ? C2 C2 H22 110.2(5) 3_666 . ? H21 C2 H22 105.0(8) . . ? C5 N1 N2 110.61(9) . . ? C5 N1 H1 130.6(7) . . ? N2 N1 H1 118.7(7) . . ? C3 N2 N1 101.85(9) . . ? N2 C3 N4 114.78(10) . . ? N2 C3 H3 121.5(5) . . ? N4 C3 H3 123.8(5) . . ? C5 N4 C3 102.60(9) . . ? N1 C5 N4 110.16(9) . . ? N1 C5 H5 122.7(6) . . ? N4 C5 H5 127.1(6) . . ? 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 O2 C1 C2 C2 -4.0(2) . . . 3_666 ? O1 C1 C2 C2 175.28(13) . . . 3_666 ? C5 N1 N2 C3 -0.43(14) . . . . ? N1 N2 C3 N4 0.34(15) . . . . ? N2 C3 N4 C5 -0.11(15) . . . . ? N2 N1 C5 N4 0.40(16) . . . . ? C3 N4 C5 N1 -0.17(15) . . . . ? 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 O1 HO1 N4 0.960(11) 1.685(11) 2.6291(12) 167.1(9) 4_666 N1 H1 O2 0.855(11) 1.946(11) 2.7901(12) 169.0(9) . C5 H5 N2 1.015(10) 2.313(10) 3.3236(17) 173.5(10) 4_465 _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 25.32 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.165 _refine_diff_density_min -0.125 _refine_diff_density_rms 0.036 data_p21c12c _database_code_depnum_ccdc_archive 'CCDC 807489' #TrackingRef '- P21C12C corrected.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Bis_1H-1,2,4-TriazoleSuccinic_Acid _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H12 N6 O4' _chemical_formula_weight 256.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P2(1)/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 5.2690(11) _cell_length_b 18.180(4) _cell_length_c 6.5540(13) _cell_angle_alpha 90.00 _cell_angle_beta 111.89(3) _cell_angle_gamma 90.00 _cell_volume 582.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 12(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'irregular cuboid' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.461 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type NONE _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 12(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 'Xcalibur- Oxford Diffraction' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4492 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0402 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 27.88 _reflns_number_total 1358 _reflns_number_gt 1070 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CRYSALIS VER 171.33.42' _computing_cell_refinement 'CRYSALIS VER 171.33.42' _computing_data_reduction 'CRYSALIS VER 171.33.42' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.1' _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^)+(0.0300P)^2^+0.8000P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0076(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1358 _refine_ls_number_parameters 108 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0708 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1146 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.134 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.08312(12) 0.46822(4) 0.78859(10) 0.01154(17) Uani 1 1 d . . . O2 O 0.80716(13) 0.39095(4) 0.53988(10) 0.01176(17) Uani 1 1 d . . . C1 C 0.84660(18) 0.44998(5) 0.63591(14) 0.0092(2) Uani 1 1 d . . . C2 C 0.63224(18) 0.50944(5) 0.59388(15) 0.0109(2) Uani 1 1 d . . . N1 N 0.62189(15) 0.24741(4) 0.44916(12) 0.0106(2) Uani 1 1 d . . . N2 N 0.83346(15) 0.20098(4) 0.55748(13) 0.0113(2) Uani 1 1 d . . . C3 C 0.71228(18) 0.13626(5) 0.52303(15) 0.0110(2) Uani 1 1 d . . . N4 N 0.43871(15) 0.13854(4) 0.40064(12) 0.0112(2) Uani 1 1 d . . . C5 C 0.39103(18) 0.20990(5) 0.35833(15) 0.0112(2) Uani 1 1 d . . . HO1 H 1.212(3) 0.4278(9) 0.827(2) 0.054(5) Uiso 1 1 d . . . H21 H 0.606(2) 0.5177(6) 0.7353(17) 0.011(3) Uiso 1 1 d . . . H22 H 0.710(2) 0.5540(6) 0.5665(16) 0.012(3) Uiso 1 1 d . . . H1 H 0.655(2) 0.2940(7) 0.4566(19) 0.023(3) Uiso 1 1 d . . . H3 H 0.8098(19) 0.0931(6) 0.5873(16) 0.008(3) Uiso 1 1 d . . . H5 H 0.223(2) 0.2306(6) 0.2765(17) 0.014(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0082(3) 0.0099(3) 0.0136(3) -0.0016(2) 0.0007(2) 0.0012(2) O2 0.0109(3) 0.0096(3) 0.0139(3) -0.0011(2) 0.0036(2) -0.0004(2) C1 0.0086(4) 0.0098(4) 0.0094(3) 0.0017(3) 0.0037(3) -0.0004(3) C2 0.0099(4) 0.0090(4) 0.0134(4) -0.0010(3) 0.0040(3) -0.0005(3) N1 0.0084(3) 0.0078(3) 0.0141(3) 0.0003(3) 0.0025(3) 0.0012(3) N2 0.0098(3) 0.0115(4) 0.0123(3) 0.0007(3) 0.0040(2) 0.0011(3) C3 0.0099(4) 0.0122(4) 0.0103(3) -0.0008(3) 0.0031(3) 0.0001(4) N4 0.0106(3) 0.0110(4) 0.0115(3) 0.0009(3) 0.0037(3) 0.0001(3) C5 0.0090(4) 0.0120(4) 0.0122(4) -0.0005(3) 0.0035(3) 0.0001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.3170(11) . ? O1 HO1 0.967(15) . ? O2 C1 1.2221(11) . ? C1 C2 1.5126(13) . ? C2 C2 1.5150(17) 3_666 ? C2 H21 0.999(12) . ? C2 H22 0.953(11) . ? N1 C5 1.3263(12) . ? N1 N2 1.3670(11) . ? N1 H1 0.863(12) . ? N2 C3 1.3175(12) . ? C3 N4 1.3641(12) . ? C3 H3 0.946(10) . ? N4 C5 1.3308(13) . ? C5 H5 0.928(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 HO1 112.3(8) . . ? O2 C1 O1 122.92(8) . . ? O2 C1 C2 124.17(8) . . ? O1 C1 C2 112.91(8) . . ? C1 C2 C2 112.60(10) . 3_666 ? C1 C2 H21 107.0(6) . . ? C2 C2 H21 112.5(6) 3_666 . ? C1 C2 H22 107.3(7) . . ? C2 C2 H22 111.6(5) 3_666 . ? H21 C2 H22 105.4(9) . . ? C5 N1 N2 110.46(8) . . ? C5 N1 H1 131.4(7) . . ? N2 N1 H1 118.0(7) . . ? C3 N2 N1 102.31(7) . . ? N2 C3 N4 114.33(8) . . ? N2 C3 H3 121.1(6) . . ? N4 C3 H3 124.5(6) . . ? C5 N4 C3 103.19(7) . . ? N1 C5 N4 109.71(8) . . ? N1 C5 H5 124.8(7) . . ? N4 C5 H5 125.5(7) . . ? 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 O2 C1 C2 C2 -4.58(17) . . . 3_666 ? O1 C1 C2 C2 175.56(10) . . . 3_666 ? C5 N1 N2 C3 0.21(11) . . . . ? N1 N2 C3 N4 -0.07(12) . . . . ? N2 C3 N4 C5 -0.10(12) . . . . ? N2 N1 C5 N4 -0.29(12) . . . . ? C3 N4 C5 N1 0.23(11) . . . . ? 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 O1 HO1 N4 0.967(15) 1.640(15) 2.6059(11) 177.5(13) 4_666 N1 H1 O2 0.863(12) 1.929(12) 2.7719(11) 165.2(10) . C5 H5 N2 0.928(10) 2.370(10) 3.2900(15) 170.9(10) 4_465 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.377 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.070