# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_shrv185 _database_code_depnum_ccdc_archive 'CCDC 879777' #TrackingRef 'shrv185-final.cif' _audit_creation_date 2012-04-16 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; 3,5-dinitro-1H-1,2,4-triazol-1-amine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C2 H2 N6 O4' _chemical_formula_sum 'C2 H2 N6 O4' _chemical_formula_weight 174.10 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 P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 8.3290(10) _cell_length_b 11.4808(15) _cell_length_c 13.6457(17) _cell_angle_alpha 78.002(4) _cell_angle_beta 77.916(4) _cell_angle_gamma 89.974(4) _cell_volume 1246.8(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description irregular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.855 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.174 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.9179 _exptl_absorpt_correction_T_max 0.9659 _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 'Bruker SMART APEX II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12125 _diffrn_reflns_av_R_equivalents 0.0145 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 26.48 _reflns_number_total 8734 _reflns_number_gt 7683 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2 v2010.3-0 (Bruker, 2009)' _computing_cell_refinement 'Bruker APEX2 v2010.3-0 (Bruker, 2009)' _computing_data_reduction ; Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008) ; _computing_structure_solution 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_structure_refinement 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_molecular_graphics 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_publication_material 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _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^)+(0.0410P)^2^+0.0931P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.4(8) _refine_ls_number_reflns 8734 _refine_ls_number_parameters 913 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.0403 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0821 _refine_ls_wR_factor_gt 0.0773 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 N1A N -0.0770(3) 0.15156(19) 0.65247(15) 0.0368(5) Uani 1 1 d . . . N2A N 0.0383(3) 0.2139(2) 0.67820(16) 0.0418(5) Uani 1 1 d . . . C3A C 0.1728(3) 0.1640(2) 0.6391(2) 0.0419(6) Uani 1 1 d . . . N4A N 0.1574(3) 0.0768(2) 0.58972(16) 0.0394(5) Uani 1 1 d . . . C5A C -0.0030(3) 0.0719(2) 0.60022(18) 0.0356(5) Uani 1 1 d . . . N6A N -0.2417(3) 0.1768(2) 0.6827(2) 0.0488(6) Uani 1 1 d D . . HAA H -0.281(4) 0.206(3) 0.6271(16) 0.059 Uiso 1 1 d D . . HAB H -0.293(4) 0.1043(16) 0.693(2) 0.059 Uiso 1 1 d D . . N7A N 0.3326(3) 0.2004(3) 0.6518(2) 0.0556(7) Uani 1 1 d . . . O8A O 0.3369(3) 0.2771(3) 0.7011(2) 0.0822(8) Uani 1 1 d . . . O9A O 0.4521(3) 0.1521(3) 0.6109(2) 0.0808(8) Uani 1 1 d . . . N10A N -0.0885(3) -0.0144(2) 0.56396(16) 0.0403(5) Uani 1 1 d . . . O11A O -0.0050(3) -0.0683(2) 0.50535(17) 0.0604(6) Uani 1 1 d . . . O12A O -0.2372(3) -0.0280(2) 0.59445(17) 0.0582(6) Uani 1 1 d . . . N1B N 0.1360(3) -0.00323(19) 0.09462(15) 0.0358(5) Uani 1 1 d . . . N2B N 0.2466(3) -0.08317(19) 0.06856(15) 0.0368(5) Uani 1 1 d . . . C3B C 0.3453(3) -0.0784(2) 0.13097(18) 0.0315(5) Uani 1 1 d . . . N4B N 0.3102(2) -0.0043(2) 0.19585(16) 0.0376(5) Uani 1 1 d . . . C5B C 0.1779(3) 0.0416(2) 0.16907(19) 0.0361(6) Uani 1 1 d . . . N6B N -0.0014(3) 0.0109(3) 0.0493(2) 0.0539(6) Uani 1 1 d D . . HBA H 0.012(4) 0.0873(13) 0.015(2) 0.065 Uiso 1 1 d D . . HBB H -0.089(3) 0.004(3) 0.1025(18) 0.065 Uiso 1 1 d D . . N7B N 0.4872(3) -0.15159(19) 0.13012(16) 0.0369(5) Uani 1 1 d . . . O8B O 0.5161(2) -0.21332(18) 0.06638(15) 0.0484(5) Uani 1 1 d . . . O9B O 0.5679(3) -0.1468(2) 0.19358(16) 0.0578(6) Uani 1 1 d . . . N10B N 0.0830(3) 0.1291(2) 0.2173(2) 0.0506(6) Uani 1 1 d . . . O11B O 0.0951(3) 0.1282(2) 0.30464(18) 0.0673(7) Uani 1 1 d . . . O12B O 0.0017(3) 0.1936(2) 0.1671(2) 0.0690(6) Uani 1 1 d . . . N1C N 0.1754(3) 0.41464(19) 0.41203(15) 0.0360(5) Uani 1 1 d . . . N2C N 0.0636(3) 0.32215(18) 0.43806(15) 0.0354(5) Uani 1 1 d . . . C3C C -0.0344(3) 0.3584(2) 0.37541(18) 0.0316(5) Uani 1 1 d . . . N4C N 0.0013(3) 0.46426(19) 0.31078(16) 0.0380(5) Uani 1 1 d . . . C5C C 0.1342(3) 0.4963(2) 0.33736(19) 0.0356(5) Uani 1 1 d . . . N6C N 0.3102(3) 0.4047(3) 0.4592(2) 0.0543(7) Uani 1 1 d D . . HCA H 0.311(5) 0.4699(19) 0.485(2) 0.065 Uiso 1 1 d D . . HCB H 0.399(3) 0.422(3) 0.4068(18) 0.065 Uiso 1 1 d D . . N7C N -0.1774(3) 0.28637(19) 0.37661(16) 0.0363(5) Uani 1 1 d . . . O8C O -0.2082(2) 0.19301(17) 0.44038(14) 0.0455(5) Uani 1 1 d . . . O9C O -0.2592(3) 0.32433(19) 0.31350(16) 0.0566(6) Uani 1 1 d . . . N10C N 0.2270(3) 0.6081(2) 0.2903(2) 0.0495(6) Uani 1 1 d . . . O11C O 0.2157(3) 0.6514(2) 0.20286(19) 0.0689(7) Uani 1 1 d . . . O12C O 0.3084(3) 0.6470(2) 0.3408(2) 0.0708(7) Uani 1 1 d . . . N1D N 0.7832(3) 0.49504(19) 0.09579(16) 0.0367(5) Uani 1 1 d . . . N2D N 0.6913(3) 0.41591(18) 0.06750(15) 0.0351(5) Uani 1 1 d . . . C3D C 0.5494(3) 0.4206(2) 0.12993(17) 0.0310(5) Uani 1 1 d . . . N4D N 0.5386(3) 0.49345(19) 0.19613(16) 0.0369(5) Uani 1 1 d . . . C5D C 0.6896(3) 0.5383(2) 0.17098(19) 0.0361(5) Uani 1 1 d . . . N6D N 0.9516(3) 0.5087(2) 0.0496(2) 0.0527(6) Uani 1 1 d D . . HDA H 0.968(4) 0.5866(11) 0.023(2) 0.063 Uiso 1 1 d D . . HDB H 0.991(4) 0.496(3) 0.1074(16) 0.063 Uiso 1 1 d D . . N7D N 0.4080(3) 0.34902(19) 0.12737(16) 0.0371(5) Uani 1 1 d . . . O8D O 0.4231(2) 0.28757(17) 0.06306(14) 0.0464(5) Uani 1 1 d . . . O9D O 0.2826(2) 0.3535(2) 0.19077(16) 0.0566(6) Uani 1 1 d . . . N10D N 0.7490(3) 0.6242(2) 0.2205(2) 0.0508(6) Uani 1 1 d . . . O11D O 0.6777(3) 0.6224(2) 0.3079(2) 0.0701(7) Uani 1 1 d . . . O12D O 0.8653(3) 0.6898(2) 0.1709(2) 0.0718(7) Uani 1 1 d . . . N1E N 0.6086(2) 0.64856(18) 0.65285(14) 0.0309(4) Uani 1 1 d . . . N2E N 0.4725(2) 0.70885(18) 0.67473(15) 0.0335(4) Uani 1 1 d . . . C3E C 0.3718(3) 0.6599(2) 0.63096(18) 0.0332(5) Uani 1 1 d . . . N4E N 0.4283(2) 0.57342(19) 0.58293(15) 0.0357(5) Uani 1 1 d . . . C5E C 0.5784(3) 0.5691(2) 0.59814(18) 0.0315(5) Uani 1 1 d . . . N6E N 0.7489(3) 0.6784(2) 0.68590(18) 0.0397(5) Uani 1 1 d D . . HEA H 0.771(3) 0.6168(18) 0.7306(17) 0.048 Uiso 1 1 d D . . HEB H 0.839(2) 0.679(3) 0.6379(17) 0.048 Uiso 1 1 d D . . N7E N 0.2038(3) 0.6973(2) 0.63608(16) 0.0406(5) Uani 1 1 d . . . O8E O 0.1568(3) 0.7704(2) 0.68677(16) 0.0575(5) Uani 1 1 d . . . O9E O 0.1217(3) 0.6507(2) 0.58971(17) 0.0604(6) Uani 1 1 d . . . N10E N 0.6941(3) 0.48363(19) 0.56447(16) 0.0390(5) Uani 1 1 d . . . O11E O 0.6473(3) 0.4199(2) 0.51465(19) 0.0640(6) Uani 1 1 d . . . O12E O 0.8252(3) 0.47946(19) 0.58913(16) 0.0543(5) Uani 1 1 d . . . N1F N 0.3740(2) 0.85080(18) 0.85199(14) 0.0334(4) Uani 1 1 d . . . N2F N 0.2511(3) 0.92115(19) 0.83333(15) 0.0362(5) Uani 1 1 d . . . C3F C 0.1226(3) 0.8487(2) 0.87889(18) 0.0341(5) Uani 1 1 d . . . N4F N 0.1490(2) 0.73881(18) 0.92674(15) 0.0350(5) Uani 1 1 d . . . C5F C 0.3092(3) 0.7435(2) 0.90773(18) 0.0322(5) Uani 1 1 d . . . N6F N 0.5369(3) 0.8951(2) 0.81495(19) 0.0464(6) Uani 1 1 d D . . HFA H 0.596(3) 0.872(3) 0.8627(18) 0.056 Uiso 1 1 d D . . HFB H 0.576(4) 0.874(3) 0.7556(14) 0.056 Uiso 1 1 d D . . N7F N -0.0431(3) 0.8834(2) 0.87386(17) 0.0469(6) Uani 1 1 d . . . O8F O -0.0611(3) 0.9817(2) 0.82464(18) 0.0677(7) Uani 1 1 d . . . O9F O -0.1537(3) 0.8110(2) 0.9185(2) 0.0753(8) Uani 1 1 d . . . N10F N 0.4040(3) 0.64175(19) 0.93962(17) 0.0401(5) Uani 1 1 d . . . O11F O 0.3258(3) 0.55552(19) 0.99560(18) 0.0635(6) Uani 1 1 d . . . O12F O 0.5516(3) 0.64874(19) 0.90829(17) 0.0567(5) Uani 1 1 d . . . N1G N 0.5266(3) 0.91723(19) 0.41271(16) 0.0370(5) Uani 1 1 d . . . N2G N 0.6198(3) 0.82461(19) 0.43802(16) 0.0368(5) Uani 1 1 d . . . C3G C 0.7617(3) 0.8613(2) 0.37448(17) 0.0313(5) Uani 1 1 d . . . N4G N 0.7696(3) 0.96738(19) 0.31039(16) 0.0369(5) Uani 1 1 d . . . C5G C 0.6185(3) 0.9989(2) 0.33777(19) 0.0349(5) Uani 1 1 d . . . N6G N 0.3592(3) 0.9075(3) 0.4592(2) 0.0583(7) Uani 1 1 d D . . HGA H 0.292(4) 0.923(3) 0.415(2) 0.070 Uiso 1 1 d D . . HGB H 0.327(5) 0.962(2) 0.498(2) 0.070 Uiso 1 1 d D . . N7G N 0.9038(3) 0.78907(19) 0.37559(16) 0.0366(5) Uani 1 1 d . . . O8G O 0.8906(2) 0.69519(17) 0.43849(14) 0.0466(5) Uani 1 1 d . . . O9G O 1.0275(2) 0.8264(2) 0.31171(16) 0.0563(5) Uani 1 1 d . . . N10G N 0.5557(3) 1.1108(2) 0.2911(2) 0.0501(6) Uani 1 1 d . . . O11G O 0.6258(3) 1.1547(2) 0.20386(19) 0.0670(7) Uani 1 1 d . . . O12G O 0.4403(3) 1.1497(2) 0.3428(2) 0.0696(7) Uani 1 1 d . . . N1H N 0.7061(2) 0.34860(19) 0.85044(15) 0.0340(4) Uani 1 1 d . . . N2H N 0.8392(3) 0.42299(19) 0.82761(16) 0.0362(5) Uani 1 1 d . . . C3H C 0.9429(3) 0.3550(2) 0.87180(18) 0.0352(5) Uani 1 1 d . . . N4H N 0.8906(3) 0.24346(18) 0.91994(15) 0.0368(5) Uani 1 1 d . . . C5H C 0.7409(3) 0.2437(2) 0.90461(18) 0.0327(5) Uani 1 1 d . . . N6H N 0.5652(3) 0.3907(2) 0.8158(2) 0.0498(6) Uani 1 1 d D . . HHA H 0.491(3) 0.396(3) 0.8733(16) 0.060 Uiso 1 1 d D . . HHB H 0.502(4) 0.3270(19) 0.821(2) 0.060 Uiso 1 1 d D . . N7H N 1.1094(3) 0.3987(2) 0.86532(18) 0.0477(6) Uani 1 1 d . . . O8H O 1.1514(3) 0.4977(2) 0.81444(18) 0.0698(7) Uani 1 1 d . . . O9H O 1.1947(3) 0.3322(2) 0.91186(18) 0.0670(7) Uani 1 1 d . . . N10H N 0.6281(3) 0.1405(2) 0.94055(17) 0.0409(5) Uani 1 1 d . . . O11H O 0.6673(3) 0.05829(19) 0.99974(18) 0.0642(6) Uani 1 1 d . . . O12H O 0.5016(3) 0.14393(19) 0.90787(17) 0.0588(6) 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 N1A 0.0389(12) 0.0385(12) 0.0355(11) -0.0127(9) -0.0087(9) 0.0066(9) N2A 0.0505(14) 0.0418(13) 0.0362(11) -0.0115(10) -0.0132(10) 0.0060(10) C3A 0.0396(15) 0.0431(15) 0.0448(15) -0.0079(12) -0.0142(12) -0.0003(12) N4A 0.0345(12) 0.0414(13) 0.0439(12) -0.0114(10) -0.0097(9) 0.0061(10) C5A 0.0385(14) 0.0349(13) 0.0353(13) -0.0076(11) -0.0120(10) 0.0021(10) N6A 0.0417(14) 0.0564(16) 0.0528(14) -0.0224(13) -0.0097(11) 0.0136(11) N7A 0.0518(16) 0.0612(17) 0.0576(16) -0.0088(14) -0.0239(13) -0.0056(13) O8A 0.0822(18) 0.096(2) 0.0852(17) -0.0376(16) -0.0385(14) -0.0166(16) O9A 0.0410(13) 0.100(2) 0.107(2) -0.0318(17) -0.0204(13) 0.0087(14) N10A 0.0449(13) 0.0355(12) 0.0414(12) -0.0098(10) -0.0095(10) 0.0023(10) O11A 0.0549(13) 0.0674(15) 0.0744(14) -0.0449(13) -0.0185(11) 0.0121(11) O12A 0.0427(12) 0.0552(13) 0.0737(14) -0.0186(11) -0.0009(10) -0.0112(10) N1B 0.0345(11) 0.0361(11) 0.0372(11) -0.0067(9) -0.0098(9) 0.0061(9) N2B 0.0410(12) 0.0336(11) 0.0363(11) -0.0077(9) -0.0090(9) 0.0061(9) C3B 0.0323(12) 0.0270(12) 0.0337(12) -0.0064(10) -0.0037(10) -0.0011(9) N4B 0.0298(11) 0.0374(12) 0.0466(12) -0.0168(10) -0.0029(9) -0.0021(9) C5B 0.0334(13) 0.0282(12) 0.0443(14) -0.0111(11) 0.0007(11) -0.0021(10) N6B 0.0520(15) 0.0600(16) 0.0569(16) -0.0143(13) -0.0262(12) 0.0187(13) N7B 0.0372(11) 0.0321(11) 0.0401(11) -0.0064(10) -0.0064(9) 0.0019(9) O8B 0.0432(11) 0.0480(11) 0.0570(12) -0.0218(10) -0.0070(9) 0.0091(9) O9B 0.0583(13) 0.0627(14) 0.0662(13) -0.0231(11) -0.0349(11) 0.0172(11) N10B 0.0376(13) 0.0407(14) 0.0745(18) -0.0292(13) 0.0021(12) -0.0044(11) O11B 0.0605(14) 0.0719(16) 0.0749(16) -0.0484(13) 0.0063(12) -0.0035(12) O12B 0.0475(13) 0.0495(13) 0.117(2) -0.0314(13) -0.0189(13) 0.0165(11) N1C 0.0386(11) 0.0329(11) 0.0381(11) -0.0101(9) -0.0092(9) 0.0002(9) N2C 0.0395(11) 0.0340(11) 0.0345(10) -0.0105(9) -0.0087(9) -0.0004(9) C3C 0.0334(12) 0.0268(12) 0.0362(12) -0.0110(10) -0.0066(10) 0.0057(10) N4C 0.0328(11) 0.0329(11) 0.0437(12) -0.0032(9) -0.0029(9) 0.0046(9) C5C 0.0326(13) 0.0301(12) 0.0410(13) -0.0066(11) -0.0018(10) 0.0033(10) N6C 0.0516(16) 0.0583(17) 0.0613(16) -0.0144(13) -0.0291(12) -0.0061(13) N7C 0.0376(11) 0.0339(12) 0.0396(11) -0.0126(10) -0.0085(9) 0.0032(9) O8C 0.0447(11) 0.0374(10) 0.0512(11) -0.0045(9) -0.0081(8) -0.0052(8) O9C 0.0590(13) 0.0547(13) 0.0635(13) -0.0062(10) -0.0355(11) -0.0024(10) N10C 0.0359(13) 0.0307(12) 0.0728(17) -0.0060(12) 0.0033(12) 0.0025(10) O11C 0.0565(13) 0.0479(13) 0.0794(17) 0.0159(12) 0.0075(11) 0.0042(10) O12C 0.0494(13) 0.0450(12) 0.118(2) -0.0209(13) -0.0148(13) -0.0088(10) N1D 0.0358(11) 0.0351(11) 0.0387(11) -0.0051(9) -0.0095(9) -0.0029(9) N2D 0.0384(11) 0.0304(11) 0.0346(10) -0.0053(9) -0.0052(9) -0.0009(9) C3D 0.0359(13) 0.0254(12) 0.0318(12) -0.0044(10) -0.0093(10) 0.0047(10) N4D 0.0357(11) 0.0366(12) 0.0437(12) -0.0147(10) -0.0139(9) 0.0103(9) C5D 0.0390(14) 0.0314(13) 0.0436(14) -0.0135(11) -0.0158(11) 0.0101(10) N6D 0.0406(14) 0.0555(16) 0.0562(16) -0.0114(13) 0.0022(11) -0.0095(12) N7D 0.0389(12) 0.0325(11) 0.0399(11) -0.0058(10) -0.0103(10) 0.0017(9) O8D 0.0492(11) 0.0431(11) 0.0536(11) -0.0194(9) -0.0169(9) 0.0019(9) O9D 0.0412(11) 0.0605(14) 0.0637(13) -0.0223(11) 0.0077(10) -0.0076(10) N10D 0.0516(15) 0.0427(14) 0.0767(18) -0.0329(13) -0.0354(14) 0.0200(12) O11D 0.0759(16) 0.0779(17) 0.0831(18) -0.0543(14) -0.0392(14) 0.0276(13) O12D 0.0582(14) 0.0464(12) 0.125(2) -0.0323(14) -0.0366(14) -0.0007(11) N1E 0.0339(11) 0.0285(10) 0.0310(10) -0.0077(8) -0.0073(8) 0.0033(8) N2E 0.0360(11) 0.0318(11) 0.0340(10) -0.0108(9) -0.0068(8) 0.0067(9) C3E 0.0336(12) 0.0337(13) 0.0311(12) -0.0048(10) -0.0061(10) 0.0028(10) N4E 0.0347(11) 0.0353(11) 0.0371(11) -0.0116(9) -0.0035(9) -0.0004(9) C5E 0.0330(13) 0.0283(12) 0.0320(12) -0.0076(10) -0.0028(9) 0.0036(9) N6E 0.0357(12) 0.0424(13) 0.0460(13) -0.0133(10) -0.0158(10) 0.0044(10) N7E 0.0357(12) 0.0495(14) 0.0358(11) -0.0082(10) -0.0067(9) 0.0053(10) O8E 0.0499(12) 0.0702(15) 0.0582(13) -0.0300(12) -0.0081(10) 0.0245(11) O9E 0.0402(11) 0.0828(16) 0.0689(14) -0.0301(12) -0.0217(10) 0.0048(11) N10E 0.0402(13) 0.0332(11) 0.0419(12) -0.0101(10) -0.0026(10) 0.0035(9) O11E 0.0546(13) 0.0609(14) 0.0905(16) -0.0521(13) -0.0113(11) 0.0091(11) O12E 0.0491(12) 0.0496(12) 0.0699(14) -0.0203(11) -0.0178(10) 0.0195(10) N1F 0.0355(11) 0.0312(11) 0.0323(10) -0.0091(9) -0.0024(8) -0.0007(9) N2F 0.0410(12) 0.0327(11) 0.0336(11) -0.0043(9) -0.0079(9) 0.0029(9) C3F 0.0361(13) 0.0341(13) 0.0323(12) -0.0059(10) -0.0091(10) 0.0042(10) N4F 0.0359(11) 0.0333(11) 0.0363(11) -0.0054(9) -0.0105(9) 0.0001(9) C5F 0.0374(13) 0.0261(12) 0.0351(12) -0.0090(10) -0.0099(10) 0.0049(10) N6F 0.0379(13) 0.0453(14) 0.0516(14) -0.0100(12) -0.0002(10) -0.0074(10) N7F 0.0423(13) 0.0583(16) 0.0398(12) -0.0052(12) -0.0129(10) 0.0094(12) O8F 0.0616(14) 0.0692(16) 0.0635(14) 0.0095(13) -0.0174(11) 0.0246(12) O9F 0.0391(12) 0.0761(17) 0.0999(19) 0.0081(15) -0.0178(12) -0.0052(12) N10F 0.0443(13) 0.0340(12) 0.0455(12) -0.0112(10) -0.0150(10) 0.0072(10) O11F 0.0597(13) 0.0371(11) 0.0860(16) 0.0139(11) -0.0253(11) -0.0013(10) O12F 0.0439(12) 0.0524(13) 0.0703(14) -0.0122(11) -0.0053(10) 0.0160(10) N1G 0.0345(11) 0.0360(11) 0.0397(11) -0.0090(9) -0.0054(9) 0.0057(9) N2G 0.0376(12) 0.0339(11) 0.0374(11) -0.0071(9) -0.0055(9) 0.0076(9) C3G 0.0324(12) 0.0309(12) 0.0321(12) -0.0100(10) -0.0071(9) -0.0024(10) N4G 0.0358(12) 0.0328(11) 0.0435(12) -0.0049(9) -0.0143(9) -0.0039(9) C5G 0.0353(13) 0.0303(12) 0.0429(13) -0.0093(11) -0.0152(11) 0.0008(10) N6G 0.0376(14) 0.0619(18) 0.0646(18) -0.0056(14) 0.0054(12) 0.0116(12) N7G 0.0380(12) 0.0353(12) 0.0384(11) -0.0115(10) -0.0087(9) 0.0028(9) O8G 0.0468(11) 0.0405(11) 0.0515(11) -0.0021(9) -0.0162(9) 0.0068(9) O9G 0.0396(11) 0.0563(13) 0.0620(13) -0.0076(10) 0.0085(9) 0.0059(9) N10G 0.0501(15) 0.0333(12) 0.0708(17) -0.0009(13) -0.0319(13) -0.0039(11) O11G 0.0779(16) 0.0448(13) 0.0768(16) 0.0123(12) -0.0383(13) -0.0078(11) O12G 0.0479(13) 0.0466(13) 0.119(2) -0.0211(13) -0.0264(13) 0.0174(11) N1H 0.0352(11) 0.0327(11) 0.0345(10) -0.0064(9) -0.0088(8) 0.0011(9) N2H 0.0379(11) 0.0326(11) 0.0367(11) -0.0040(9) -0.0082(9) -0.0010(9) C3H 0.0351(13) 0.0374(14) 0.0320(12) -0.0069(11) -0.0049(10) -0.0009(11) N4H 0.0359(12) 0.0341(11) 0.0376(11) -0.0060(9) -0.0035(9) 0.0056(9) C5H 0.0352(13) 0.0293(12) 0.0322(12) -0.0081(10) -0.0025(10) -0.0008(10) N6H 0.0406(14) 0.0473(14) 0.0594(15) 0.0018(12) -0.0190(11) -0.0004(11) N7H 0.0359(13) 0.0588(16) 0.0464(13) -0.0106(12) -0.0049(10) -0.0050(11) O8H 0.0619(14) 0.0693(16) 0.0658(14) 0.0071(13) -0.0074(11) -0.0282(12) O9H 0.0394(11) 0.0825(17) 0.0778(15) -0.0048(13) -0.0221(11) 0.0038(11) N10H 0.0410(13) 0.0310(12) 0.0462(13) -0.0082(10) 0.0008(10) 0.0009(9) O11H 0.0603(14) 0.0407(12) 0.0789(15) 0.0101(11) -0.0092(11) -0.0016(10) O12H 0.0533(13) 0.0509(12) 0.0747(14) -0.0142(11) -0.0182(11) -0.0111(10) _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 N1A N2A 1.343(3) . ? N1A C5A 1.346(3) . ? N1A N6A 1.396(3) . ? N2A C3A 1.321(4) . ? C3A N4A 1.337(4) . ? C3A N7A 1.450(4) . ? C3A C5A 2.025(3) . ? N4A C5A 1.313(3) . ? C5A N10A 1.445(3) . ? N6A HAA 0.890(10) . ? N6A HAB 0.906(10) . ? N7A O8A 1.220(4) . ? N7A O9A 1.226(4) . ? N10A O11A 1.215(3) . ? N10A O12A 1.220(3) . ? N1B C5B 1.336(3) . ? N1B N2B 1.348(3) . ? N1B N6B 1.405(3) . ? N2B C3B 1.310(3) . ? C3B N4B 1.341(3) . ? C3B N7B 1.449(3) . ? C3B C5B 2.026(4) . ? N4B C5B 1.309(3) . ? C5B N10B 1.457(4) . ? N6B HBA 0.900(10) . ? N6B HBB 0.905(10) . ? N7B O9B 1.212(3) . ? N7B O8B 1.219(3) . ? N10B O12B 1.208(3) . ? N10B O11B 1.215(3) . ? N1C C5C 1.336(3) . ? N1C N2C 1.352(3) . ? N1C N6C 1.400(3) . ? N2C C3C 1.309(3) . ? C3C N4C 1.337(3) . ? C3C N7C 1.445(3) . ? C3C C5C 2.026(3) . ? N4C C5C 1.310(3) . ? C5C N10C 1.452(3) . ? N6C HCA 0.892(10) . ? N6C HCB 0.906(10) . ? N7C O9C 1.218(3) . ? N7C O8C 1.221(3) . ? N10C O12C 1.207(3) . ? N10C O11C 1.217(3) . ? N1D C5D 1.335(3) . ? N1D N2D 1.353(3) . ? N1D N6D 1.407(3) . ? N2D C3D 1.312(3) . ? C3D N4D 1.343(3) . ? C3D N7D 1.447(3) . ? C3D C5D 2.022(3) . ? N4D C5D 1.308(3) . ? C5D N10D 1.447(3) . ? N6D HDA 0.892(10) . ? N6D HDB 0.899(10) . ? N7D O9D 1.218(3) . ? N7D O8D 1.223(3) . ? N10D O11D 1.212(3) . ? N10D O12D 1.215(3) . ? N1E N2E 1.340(3) . ? N1E C5E 1.347(3) . ? N1E N6E 1.405(3) . ? N2E C3E 1.314(3) . ? C3E N4E 1.333(3) . ? C3E N7E 1.455(3) . ? C3E C5E 2.029(4) . ? N4E C5E 1.308(3) . ? C5E N10E 1.451(3) . ? N6E HEA 0.880(10) . ? N6E HEB 0.889(10) . ? N7E O8E 1.210(3) . ? N7E O9E 1.215(3) . ? N10E O12E 1.206(3) . ? N10E O11E 1.212(3) . ? N1F N2F 1.337(3) . ? N1F C5F 1.351(3) . ? N1F N6F 1.400(3) . ? N2F C3F 1.316(3) . ? C3F N4F 1.336(3) . ? C3F N7F 1.448(3) . ? C3F C5F 2.022(4) . ? N4F C5F 1.304(3) . ? C5F N10F 1.453(3) . ? N6F HFA 0.895(10) . ? N6F HFB 0.891(10) . ? N7F O9F 1.210(3) . ? N7F O8F 1.214(3) . ? N10F O12F 1.211(3) . ? N10F O11F 1.211(3) . ? N1G C5G 1.337(3) . ? N1G N2G 1.346(3) . ? N1G N6G 1.400(3) . ? N2G C3G 1.321(3) . ? C3G N4G 1.336(3) . ? C3G N7G 1.446(3) . ? C3G C5G 2.022(4) . ? N4G C5G 1.309(3) . ? C5G N10G 1.459(3) . ? N6G HGA 0.903(10) . ? N6G HGB 0.908(10) . ? N7G O9G 1.214(3) . ? N7G O8G 1.219(3) . ? N10G O12G 1.212(3) . ? N10G O11G 1.213(3) . ? N1H C5H 1.342(3) . ? N1H N2H 1.342(3) . ? N1H N6H 1.403(3) . ? N2H C3H 1.320(3) . ? C3H N4H 1.338(3) . ? C3H N7H 1.454(3) . ? C3H C5H 2.028(3) . ? N4H C5H 1.307(3) . ? C5H N10H 1.446(3) . ? N6H HHA 0.904(10) . ? N6H HHB 0.882(10) . ? N7H O8H 1.211(3) . ? N7H O9H 1.216(3) . ? N10H O11H 1.202(3) . ? N10H O12H 1.225(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2A N1A C5A 108.8(2) . . ? N2A N1A N6A 118.7(2) . . ? C5A N1A N6A 132.4(2) . . ? C3A N2A N1A 100.8(2) . . ? N2A C3A N4A 118.3(2) . . ? N2A C3A N7A 120.9(3) . . ? N4A C3A N7A 120.8(3) . . ? N2A C3A C5A 78.53(17) . . ? N4A C3A C5A 39.74(14) . . ? N7A C3A C5A 160.5(3) . . ? C5A N4A C3A 99.6(2) . . ? N4A C5A N1A 112.5(2) . . ? N4A C5A N10A 122.9(2) . . ? N1A C5A N10A 124.6(2) . . ? N4A C5A C3A 40.63(15) . . ? N1A C5A C3A 71.83(16) . . ? N10A C5A C3A 163.3(2) . . ? N1A N6A HAA 109(2) . . ? N1A N6A HAB 102(2) . . ? HAA N6A HAB 93(3) . . ? O8A N7A O9A 125.6(3) . . ? O8A N7A C3A 117.3(3) . . ? O9A N7A C3A 117.0(3) . . ? O11A N10A O12A 125.3(2) . . ? O11A N10A C5A 116.7(2) . . ? O12A N10A C5A 118.0(2) . . ? C5B N1B N2B 108.6(2) . . ? C5B N1B N6B 132.4(2) . . ? N2B N1B N6B 118.8(2) . . ? C3B N2B N1B 101.1(2) . . ? N2B C3B N4B 117.9(2) . . ? N2B C3B N7B 120.9(2) . . ? N4B C3B N7B 121.2(2) . . ? N2B C3B C5B 78.33(17) . . ? N4B C3B C5B 39.53(13) . . ? N7B C3B C5B 160.76(19) . . ? C5B N4B C3B 99.8(2) . . ? N4B C5B N1B 112.7(2) . . ? N4B C5B N10B 123.9(2) . . ? N1B C5B N10B 123.4(2) . . ? N4B C5B C3B 40.71(14) . . ? N1B C5B C3B 71.96(16) . . ? N10B C5B C3B 164.6(2) . . ? N1B N6B HBA 103(2) . . ? N1B N6B HBB 105(2) . . ? HBA N6B HBB 109(3) . . ? O9B N7B O8B 125.0(2) . . ? O9B N7B C3B 117.1(2) . . ? O8B N7B C3B 117.9(2) . . ? O12B N10B O11B 127.4(3) . . ? O12B N10B C5B 117.3(3) . . ? O11B N10B C5B 115.3(3) . . ? C5C N1C N2C 108.43(19) . . ? C5C N1C N6C 133.3(2) . . ? N2C N1C N6C 118.0(2) . . ? C3C N2C N1C 101.10(19) . . ? N2C C3C N4C 118.0(2) . . ? N2C C3C N7C 120.9(2) . . ? N4C C3C N7C 121.1(2) . . ? N2C C3C C5C 78.40(16) . . ? N4C C3C C5C 39.58(13) . . ? N7C C3C C5C 160.64(19) . . ? C5C N4C C3C 99.8(2) . . ? N4C C5C N1C 112.6(2) . . ? N4C C5C N10C 123.6(2) . . ? N1C C5C N10C 123.7(2) . . ? N4C C5C C3C 40.58(13) . . ? N1C C5C C3C 72.07(15) . . ? N10C C5C C3C 164.2(2) . . ? N1C N6C HCA 105(2) . . ? N1C N6C HCB 105(2) . . ? HCA N6C HCB 100(3) . . ? O9C N7C O8C 124.8(2) . . ? O9C N7C C3C 117.0(2) . . ? O8C N7C C3C 118.2(2) . . ? O12C N10C O11C 127.1(2) . . ? O12C N10C C5C 117.2(3) . . ? O11C N10C C5C 115.7(3) . . ? C5D N1D N2D 108.9(2) . . ? C5D N1D N6D 133.4(2) . . ? N2D N1D N6D 117.5(2) . . ? C3D N2D N1D 100.4(2) . . ? N2D C3D N4D 118.5(2) . . ? N2D C3D N7D 120.7(2) . . ? N4D C3D N7D 120.8(2) . . ? N2D C3D C5D 78.83(16) . . ? N4D C3D C5D 39.64(13) . . ? N7D C3D C5D 160.4(2) . . ? C5D N4D C3D 99.4(2) . . ? N4D C5D N1D 112.8(2) . . ? N4D C5D N10D 123.5(2) . . ? N1D C5D N10D 123.7(2) . . ? N4D C5D C3D 40.92(13) . . ? N1D C5D C3D 71.88(15) . . ? N10D C5D C3D 164.4(2) . . ? N1D N6D HDA 104(2) . . ? N1D N6D HDB 98(2) . . ? HDA N6D HDB 106(3) . . ? O9D N7D O8D 124.7(2) . . ? O9D N7D C3D 117.2(2) . . ? O8D N7D C3D 118.1(2) . . ? O11D N10D O12D 126.8(3) . . ? O11D N10D C5D 116.1(3) . . ? O12D N10D C5D 117.1(3) . . ? N2E N1E C5E 108.45(19) . . ? N2E N1E N6E 118.57(19) . . ? C5E N1E N6E 133.0(2) . . ? C3E N2E N1E 101.53(19) . . ? N2E C3E N4E 117.6(2) . . ? N2E C3E N7E 121.3(2) . . ? N4E C3E N7E 121.2(2) . . ? N2E C3E C5E 78.20(16) . . ? N4E C3E C5E 39.37(13) . . ? N7E C3E C5E 160.5(2) . . ? C5E N4E C3E 100.4(2) . . ? N4E C5E N1E 112.1(2) . . ? N4E C5E N10E 123.3(2) . . ? N1E C5E N10E 124.5(2) . . ? N4E C5E C3E 40.27(14) . . ? N1E C5E C3E 71.82(16) . . ? N10E C5E C3E 163.41(19) . . ? N1E N6E HEA 108.5(19) . . ? N1E N6E HEB 111.2(19) . . ? HEA N6E HEB 97(3) . . ? O8E N7E O9E 125.5(2) . . ? O8E N7E C3E 117.8(2) . . ? O9E N7E C3E 116.7(2) . . ? O12E N10E O11E 125.4(2) . . ? O12E N10E C5E 118.8(2) . . ? O11E N10E C5E 115.7(2) . . ? N2F N1F C5F 108.62(19) . . ? N2F N1F N6F 119.6(2) . . ? C5F N1F N6F 131.8(2) . . ? C3F N2F N1F 101.08(19) . . ? N2F C3F N4F 118.1(2) . . ? N2F C3F N7F 121.8(2) . . ? N4F C3F N7F 120.1(2) . . ? N2F C3F C5F 78.62(16) . . ? N4F C3F C5F 39.45(13) . . ? N7F C3F C5F 159.3(2) . . ? C5F N4F C3F 99.9(2) . . ? N4F C5F N1F 112.3(2) . . ? N4F C5F N10F 122.7(2) . . ? N1F C5F N10F 124.9(2) . . ? N4F C5F C3F 40.61(13) . . ? N1F C5F C3F 71.67(15) . . ? N10F C5F C3F 163.18(19) . . ? N1F N6F HFA 110(2) . . ? N1F N6F HFB 109(2) . . ? HFA N6F HFB 114(3) . . ? O9F N7F O8F 124.8(3) . . ? O9F N7F C3F 117.1(2) . . ? O8F N7F C3F 118.0(2) . . ? O12F N10F O11F 125.5(2) . . ? O12F N10F C5F 118.6(2) . . ? O11F N10F C5F 115.8(2) . . ? C5G N1G N2G 108.6(2) . . ? C5G N1G N6G 132.9(2) . . ? N2G N1G N6G 118.2(2) . . ? C3G N2G N1G 100.9(2) . . ? N2G C3G N4G 117.9(2) . . ? N2G C3G N7G 120.7(2) . . ? N4G C3G N7G 121.4(2) . . ? N2G C3G C5G 78.23(16) . . ? N4G C3G C5G 39.64(14) . . ? N7G C3G C5G 161.01(18) . . ? C5G N4G C3G 99.7(2) . . ? N4G C5G N1G 112.9(2) . . ? N4G C5G N10G 123.8(2) . . ? N1G C5G N10G 123.2(2) . . ? N4G C5G C3G 40.65(13) . . ? N1G C5G C3G 72.27(15) . . ? N10G C5G C3G 164.5(2) . . ? N1G N6G HGA 114(2) . . ? N1G N6G HGB 114(2) . . ? HGA N6G HGB 101(3) . . ? O9G N7G O8G 124.9(2) . . ? O9G N7G C3G 116.8(2) . . ? O8G N7G C3G 118.3(2) . . ? O12G N10G O11G 127.1(3) . . ? O12G N10G C5G 117.2(3) . . ? O11G N10G C5G 115.7(3) . . ? C5H N1H N2H 108.68(19) . . ? C5H N1H N6H 133.1(2) . . ? N2H N1H N6H 118.2(2) . . ? C3H N2H N1H 101.19(19) . . ? N2H C3H N4H 117.5(2) . . ? N2H C3H N7H 121.0(2) . . ? N4H C3H N7H 121.4(2) . . ? N2H C3H C5H 78.15(16) . . ? N4H C3H C5H 39.39(13) . . ? N7H C3H C5H 160.8(2) . . ? C5H N4H C3H 100.1(2) . . ? N4H C5H N1H 112.5(2) . . ? N4H C5H N10H 123.1(2) . . ? N1H C5H N10H 124.4(2) . . ? N4H C5H C3H 40.52(13) . . ? N1H C5H C3H 71.98(15) . . ? N10H C5H C3H 163.6(2) . . ? N1H N6H HHA 105(2) . . ? N1H N6H HHB 106(2) . . ? HHA N6H HHB 81(3) . . ? O8H N7H O9H 125.6(2) . . ? O8H N7H C3H 117.6(3) . . ? O9H N7H C3H 116.8(2) . . ? O11H N10H O12H 125.5(2) . . ? O11H N10H C5H 116.9(2) . . ? O12H N10H C5H 117.5(2) . . ? 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 C5A N1A N2A C3A -0.6(3) . . . . ? N6A N1A N2A C3A 178.8(2) . . . . ? N1A N2A C3A N4A 0.7(3) . . . . ? N1A N2A C3A N7A -177.6(2) . . . . ? N1A N2A C3A C5A 0.38(16) . . . . ? N2A C3A N4A C5A -0.5(3) . . . . ? N7A C3A N4A C5A 177.8(2) . . . . ? C3A N4A C5A N1A 0.1(3) . . . . ? C3A N4A C5A N10A -176.8(2) . . . . ? N2A N1A C5A N4A 0.3(3) . . . . ? N6A N1A C5A N4A -178.9(3) . . . . ? N2A N1A C5A N10A 177.2(2) . . . . ? N6A N1A C5A N10A -2.1(4) . . . . ? N2A N1A C5A C3A 0.40(17) . . . . ? N6A N1A C5A C3A -178.9(3) . . . . ? N2A C3A C5A N4A 179.5(3) . . . . ? N7A C3A C5A N4A -5.7(6) . . . . ? N2A C3A C5A N1A -0.40(17) . . . . ? N4A C3A C5A N1A -179.9(3) . . . . ? N7A C3A C5A N1A 174.4(6) . . . . ? N2A C3A C5A N10A -171.0(7) . . . . ? N4A C3A C5A N10A 9.4(7) . . . . ? N7A C3A C5A N10A 3.8(12) . . . . ? N2A C3A N7A O8A 1.1(4) . . . . ? N4A C3A N7A O8A -177.1(3) . . . . ? C5A C3A N7A O8A -172.9(5) . . . . ? N2A C3A N7A O9A -178.1(3) . . . . ? N4A C3A N7A O9A 3.6(4) . . . . ? C5A C3A N7A O9A 7.8(8) . . . . ? N4A C5A N10A O11A -14.0(4) . . . . ? N1A C5A N10A O11A 169.5(2) . . . . ? C3A C5A N10A O11A -21.3(8) . . . . ? N4A C5A N10A O12A 165.7(2) . . . . ? N1A C5A N10A O12A -10.8(4) . . . . ? C3A C5A N10A O12A 158.4(6) . . . . ? C5B N1B N2B C3B 0.1(2) . . . . ? N6B N1B N2B C3B -174.9(2) . . . . ? N1B N2B C3B N4B 0.5(3) . . . . ? N1B N2B C3B N7B -179.86(19) . . . . ? N1B N2B C3B C5B -0.05(15) . . . . ? N2B C3B N4B C5B -0.9(3) . . . . ? N7B C3B N4B C5B 179.5(2) . . . . ? C3B N4B C5B N1B 0.9(3) . . . . ? C3B N4B C5B N10B 178.9(2) . . . . ? N2B N1B C5B N4B -0.6(3) . . . . ? N6B N1B C5B N4B 173.4(3) . . . . ? N2B N1B C5B N10B -178.7(2) . . . . ? N6B N1B C5B N10B -4.7(4) . . . . ? N2B N1B C5B C3B -0.06(16) . . . . ? N6B N1B C5B C3B 174.0(3) . . . . ? N2B C3B C5B N4B 179.2(2) . . . . ? N7B C3B C5B N4B -1.3(5) . . . . ? N2B C3B C5B N1B 0.06(16) . . . . ? N4B C3B C5B N1B -179.2(2) . . . . ? N7B C3B C5B N1B 179.6(5) . . . . ? N2B C3B C5B N10B 175.7(7) . . . . ? N4B C3B C5B N10B -3.5(7) . . . . ? N7B C3B C5B N10B -4.8(11) . . . . ? N2B C3B N7B O9B -176.4(2) . . . . ? N4B C3B N7B O9B 3.3(3) . . . . ? C5B C3B N7B O9B 4.2(6) . . . . ? N2B C3B N7B O8B 3.4(3) . . . . ? N4B C3B N7B O8B -177.0(2) . . . . ? C5B C3B N7B O8B -176.0(5) . . . . ? N4B C5B N10B O12B 155.4(2) . . . . ? N1B C5B N10B O12B -26.8(3) . . . . ? C3B C5B N10B O12B 158.2(6) . . . . ? N4B C5B N10B O11B -24.7(3) . . . . ? N1B C5B N10B O11B 153.1(2) . . . . ? C3B C5B N10B O11B -22.0(8) . . . . ? C5C N1C N2C C3C 0.0(3) . . . . ? N6C N1C N2C C3C -175.6(2) . . . . ? N1C N2C C3C N4C 0.3(3) . . . . ? N1C N2C C3C N7C -179.3(2) . . . . ? N1C N2C C3C C5C -0.02(16) . . . . ? N2C C3C N4C C5C -0.5(3) . . . . ? N7C C3C N4C C5C 179.1(2) . . . . ? C3C N4C C5C N1C 0.5(3) . . . . ? C3C N4C C5C N10C -179.8(2) . . . . ? N2C N1C C5C N4C -0.4(3) . . . . ? N6C N1C C5C N4C 174.4(3) . . . . ? N2C N1C C5C N10C 180.0(2) . . . . ? N6C N1C C5C N10C -5.3(5) . . . . ? N2C N1C C5C C3C -0.02(17) . . . . ? N6C N1C C5C C3C 174.7(3) . . . . ? N2C C3C C5C N4C 179.5(3) . . . . ? N7C C3C C5C N4C -2.3(6) . . . . ? N2C C3C C5C N1C 0.02(17) . . . . ? N4C C3C C5C N1C -179.5(3) . . . . ? N7C C3C C5C N1C 178.1(6) . . . . ? N2C C3C C5C N10C -180.0(8) . . . . ? N4C C3C C5C N10C 0.5(7) . . . . ? N7C C3C C5C N10C -1.9(12) . . . . ? N2C C3C N7C O9C -177.5(2) . . . . ? N4C C3C N7C O9C 2.9(3) . . . . ? C5C C3C N7C O9C 4.7(7) . . . . ? N2C C3C N7C O8C 2.9(3) . . . . ? N4C C3C N7C O8C -176.7(2) . . . . ? C5C C3C N7C O8C -175.0(5) . . . . ? N4C C5C N10C O12C 155.1(3) . . . . ? N1C C5C N10C O12C -25.3(4) . . . . ? C3C C5C N10C O12C 154.7(7) . . . . ? N4C C5C N10C O11C -26.0(4) . . . . ? N1C C5C N10C O11C 153.6(3) . . . . ? C3C C5C N10C O11C -26.4(9) . . . . ? C5D N1D N2D C3D 0.2(2) . . . . ? N6D N1D N2D C3D 175.5(2) . . . . ? N1D N2D C3D N4D -0.3(3) . . . . ? N1D N2D C3D N7D 179.6(2) . . . . ? N1D N2D C3D C5D -0.11(16) . . . . ? N2D C3D N4D C5D 0.4(3) . . . . ? N7D C3D N4D C5D -179.6(2) . . . . ? C3D N4D C5D N1D -0.2(3) . . . . ? C3D N4D C5D N10D -179.4(2) . . . . ? N2D N1D C5D N4D 0.0(3) . . . . ? N6D N1D C5D N4D -174.2(3) . . . . ? N2D N1D C5D N10D 179.2(2) . . . . ? N6D N1D C5D N10D 5.0(4) . . . . ? N2D N1D C5D C3D -0.12(17) . . . . ? N6D N1D C5D C3D -174.4(3) . . . . ? N2D C3D C5D N4D -179.7(2) . . . . ? N7D C3D C5D N4D 1.0(5) . . . . ? N2D C3D C5D N1D 0.12(17) . . . . ? N4D C3D C5D N1D 179.8(3) . . . . ? N7D C3D C5D N1D -179.2(5) . . . . ? N2D C3D C5D N10D -177.8(7) . . . . ? N4D C3D C5D N10D 1.9(7) . . . . ? N7D C3D C5D N10D 2.8(11) . . . . ? N2D C3D N7D O9D 176.5(2) . . . . ? N4D C3D N7D O9D -3.5(3) . . . . ? C5D C3D N7D O9D -4.2(6) . . . . ? N2D C3D N7D O8D -2.6(3) . . . . ? N4D C3D N7D O8D 177.3(2) . . . . ? C5D C3D N7D O8D 176.6(5) . . . . ? N4D C5D N10D O11D 26.1(4) . . . . ? N1D C5D N10D O11D -153.0(3) . . . . ? C3D C5D N10D O11D 24.6(9) . . . . ? N4D C5D N10D O12D -154.5(3) . . . . ? N1D C5D N10D O12D 26.4(4) . . . . ? C3D C5D N10D O12D -155.9(7) . . . . ? C5E N1E N2E C3E 0.0(2) . . . . ? N6E N1E N2E C3E 178.6(2) . . . . ? N1E N2E C3E N4E 0.2(3) . . . . ? N1E N2E C3E N7E 179.2(2) . . . . ? N1E N2E C3E C5E -0.02(15) . . . . ? N2E C3E N4E C5E -0.3(3) . . . . ? N7E C3E N4E C5E -179.4(2) . . . . ? C3E N4E C5E N1E 0.3(3) . . . . ? C3E N4E C5E N10E 177.1(2) . . . . ? N2E N1E C5E N4E -0.2(3) . . . . ? N6E N1E C5E N4E -178.5(2) . . . . ? N2E N1E C5E N10E -177.0(2) . . . . ? N6E N1E C5E N10E 4.8(4) . . . . ? N2E N1E C5E C3E -0.02(16) . . . . ? N6E N1E C5E C3E -178.3(3) . . . . ? N2E C3E C5E N4E 179.7(2) . . . . ? N7E C3E C5E N4E 1.7(5) . . . . ? N2E C3E C5E N1E 0.02(16) . . . . ? N4E C3E C5E N1E -179.7(2) . . . . ? N7E C3E C5E N1E -178.0(6) . . . . ? N2E C3E C5E N10E 171.2(7) . . . . ? N4E C3E C5E N10E -8.5(6) . . . . ? N7E C3E C5E N10E -6.9(11) . . . . ? N2E C3E N7E O8E -4.0(3) . . . . ? N4E C3E N7E O8E 175.0(2) . . . . ? C5E C3E N7E O8E 173.8(5) . . . . ? N2E C3E N7E O9E 176.9(2) . . . . ? N4E C3E N7E O9E -4.1(3) . . . . ? C5E C3E N7E O9E -5.3(7) . . . . ? N4E C5E N10E O12E -173.9(2) . . . . ? N1E C5E N10E O12E 2.5(4) . . . . ? C3E C5E N10E O12E -167.3(6) . . . . ? N4E C5E N10E O11E 4.6(3) . . . . ? N1E C5E N10E O11E -179.0(2) . . . . ? C3E C5E N10E O11E 11.2(8) . . . . ? C5F N1F N2F C3F -0.7(2) . . . . ? N6F N1F N2F C3F 179.7(2) . . . . ? N1F N2F C3F N4F 1.0(3) . . . . ? N1F N2F C3F N7F -175.9(2) . . . . ? N1F N2F C3F C5F 0.46(16) . . . . ? N2F C3F N4F C5F -0.8(3) . . . . ? N7F C3F N4F C5F 176.2(2) . . . . ? C3F N4F C5F N1F 0.3(3) . . . . ? C3F N4F C5F N10F -177.0(2) . . . . ? N2F N1F C5F N4F 0.3(3) . . . . ? N6F N1F C5F N4F 179.8(2) . . . . ? N2F N1F C5F N10F 177.5(2) . . . . ? N6F N1F C5F N10F -3.0(4) . . . . ? N2F N1F C5F C3F 0.48(16) . . . . ? N6F N1F C5F C3F 180.0(3) . . . . ? N2F C3F C5F N4F 179.2(3) . . . . ? N7F C3F C5F N4F -9.4(5) . . . . ? N2F C3F C5F N1F -0.47(16) . . . . ? N4F C3F C5F N1F -179.7(3) . . . . ? N7F C3F C5F N1F 170.8(6) . . . . ? N2F C3F C5F N10F -171.9(7) . . . . ? N4F C3F C5F N10F 8.8(7) . . . . ? N7F C3F C5F N10F -0.6(11) . . . . ? N2F C3F N7F O9F -179.7(3) . . . . ? N4F C3F N7F O9F 3.4(4) . . . . ? C5F C3F N7F O9F 10.3(7) . . . . ? N2F C3F N7F O8F 1.1(4) . . . . ? N4F C3F N7F O8F -175.8(3) . . . . ? C5F C3F N7F O8F -168.9(5) . . . . ? N4F C5F N10F O12F 171.0(2) . . . . ? N1F C5F N10F O12F -5.9(4) . . . . ? C3F C5F N10F O12F 164.2(6) . . . . ? N4F C5F N10F O11F -8.3(4) . . . . ? N1F C5F N10F O11F 174.8(2) . . . . ? C3F C5F N10F O11F -15.2(8) . . . . ? C5G N1G N2G C3G 0.3(3) . . . . ? N6G N1G N2G C3G 175.0(2) . . . . ? N1G N2G C3G N4G -0.5(3) . . . . ? N1G N2G C3G N7G 178.8(2) . . . . ? N1G N2G C3G C5G -0.17(16) . . . . ? N2G C3G N4G C5G 0.4(3) . . . . ? N7G C3G N4G C5G -178.8(2) . . . . ? C3G N4G C5G N1G -0.2(3) . . . . ? C3G N4G C5G N10G -179.6(2) . . . . ? N2G N1G C5G N4G 0.0(3) . . . . ? N6G N1G C5G N4G -173.6(3) . . . . ? N2G N1G C5G N10G 179.4(2) . . . . ? N6G N1G C5G N10G 5.8(5) . . . . ? N2G N1G C5G C3G -0.18(17) . . . . ? N6G N1G C5G C3G -173.8(3) . . . . ? N2G C3G C5G N4G -179.6(3) . . . . ? N7G C3G C5G N4G 3.1(5) . . . . ? N2G C3G C5G N1G 0.18(17) . . . . ? N4G C3G C5G N1G 179.8(3) . . . . ? N7G C3G C5G N1G -177.2(5) . . . . ? N2G C3G C5G N10G -178.5(7) . . . . ? N4G C3G C5G N10G 1.1(7) . . . . ? N7G C3G C5G N10G 4.2(11) . . . . ? N2G C3G N7G O9G 176.7(2) . . . . ? N4G C3G N7G O9G -4.0(3) . . . . ? C5G C3G N7G O9G -6.3(7) . . . . ? N2G C3G N7G O8G -2.0(3) . . . . ? N4G C3G N7G O8G 177.2(2) . . . . ? C5G C3G N7G O8G 174.9(5) . . . . ? N4G C5G N10G O12G -154.5(3) . . . . ? N1G C5G N10G O12G 26.1(4) . . . . ? C3G C5G N10G O12G -155.4(7) . . . . ? N4G C5G N10G O11G 25.5(4) . . . . ? N1G C5G N10G O11G -153.9(2) . . . . ? C3G C5G N10G O11G 24.6(8) . . . . ? C5H N1H N2H C3H -0.6(3) . . . . ? N6H N1H N2H C3H 179.7(2) . . . . ? N1H N2H C3H N4H 0.8(3) . . . . ? N1H N2H C3H N7H 178.8(2) . . . . ? N1H N2H C3H C5H 0.36(16) . . . . ? N2H C3H N4H C5H -0.6(3) . . . . ? N7H C3H N4H C5H -178.6(2) . . . . ? C3H N4H C5H N1H 0.2(3) . . . . ? C3H N4H C5H N10H 178.8(2) . . . . ? N2H N1H C5H N4H 0.3(3) . . . . ? N6H N1H C5H N4H 180.0(3) . . . . ? N2H N1H C5H N10H -178.4(2) . . . . ? N6H N1H C5H N10H 1.4(4) . . . . ? N2H N1H C5H C3H 0.38(17) . . . . ? N6H N1H C5H C3H -179.9(3) . . . . ? N2H C3H C5H N4H 179.4(3) . . . . ? N7H C3H C5H N4H 3.5(6) . . . . ? N2H C3H C5H N1H -0.37(17) . . . . ? N4H C3H C5H N1H -179.8(3) . . . . ? N7H C3H C5H N1H -176.3(6) . . . . ? N2H C3H C5H N10H 176.0(7) . . . . ? N4H C3H C5H N10H -3.5(6) . . . . ? N7H C3H C5H N10H 0.1(11) . . . . ? N2H C3H N7H O8H -3.0(4) . . . . ? N4H C3H N7H O8H 174.9(3) . . . . ? C5H C3H N7H O8H 172.3(5) . . . . ? N2H C3H N7H O9H 176.9(3) . . . . ? N4H C3H N7H O9H -5.1(4) . . . . ? C5H C3H N7H O9H -7.7(7) . . . . ? N4H C5H N10H O11H 11.4(4) . . . . ? N1H C5H N10H O11H -170.1(3) . . . . ? C3H C5H N10H O11H 14.1(8) . . . . ? N4H C5H N10H O12H -168.2(2) . . . . ? N1H C5H N10H O12H 10.3(4) . . . . ? C3H C5H N10H O12H -165.5(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N6A HAA O9A 0.890(10) 2.38(3) 2.951(3) 123(2) 1_455 N6A HAB O12A 0.906(10) 2.22(3) 2.852(4) 127(3) . N6B HBA N4H 0.900(10) 2.34(2) 3.123(3) 145(3) 1_454 N6C HCA N4E 0.892(10) 2.32(2) 3.103(3) 147(3) . N6D HDA N4F 0.892(10) 2.29(2) 3.082(3) 147(3) 1_654 N6E HEA N2H 0.880(10) 2.472(12) 3.340(3) 169(3) . N6E HEB O9E 0.889(10) 2.345(17) 3.151(3) 151(3) 1_655 N6F HFA O9F 0.895(10) 2.419(17) 3.244(3) 153(3) 1_655 N6F HFB O12A 0.891(10) 2.46(2) 3.146(3) 134(3) 1_665 N6G HGA O11A 0.903(10) 2.53(3) 2.991(3) 112(3) 1_565 N6G HGB N4A 0.908(10) 2.289(17) 3.155(4) 159(3) 1_565 N6H HHA O9H 0.904(10) 2.49(3) 3.104(3) 126(3) 1_455 N6H HHB O12H 0.882(10) 2.19(3) 2.851(3) 132(3) . _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 26.48 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.159 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.040 data_shrv187 _database_code_depnum_ccdc_archive 'CCDC 879779' #TrackingRef 'shrv187-final.cif' _audit_creation_date 2012-05-01 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; 4,5-dinitro-2H-1,2,3-triazol-2-amine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C2 H2 N6 O4' _chemical_formula_sum 'C2 H2 N6 O4' _chemical_formula_weight 174.10 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 8.044(4) _cell_length_b 16.110(6) _cell_length_c 4.998(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.119(5) _cell_angle_gamma 90.00 _cell_volume 619.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.868 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.176 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.9691 _exptl_absorpt_correction_T_max 0.9913 _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 'Bruker SMART APEX II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 2355 _diffrn_reflns_av_R_equivalents 0.0393 _diffrn_reflns_av_sigmaI/netI 0.0413 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 26.25 _reflns_number_total 1218 _reflns_number_gt 904 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2 v2010.3-0 (Bruker, 2009)' _computing_cell_refinement 'Bruker APEX2 v2010.3-0 (Bruker, 2009)' _computing_data_reduction ; Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008) ; _computing_structure_solution 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_structure_refinement 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_molecular_graphics 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_publication_material 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _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^)+(0.0448P)^2^+0.1107P] 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 1218 _refine_ls_number_parameters 115 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.1015 _refine_ls_wR_factor_gt 0.0889 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.085 _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 0.6725(2) 0.40631(11) 0.1020(4) 0.0339(4) Uani 1 1 d . . . C2 C 0.7318(2) 0.35592(11) 0.3337(4) 0.0329(4) Uani 1 1 d . . . N3 N 0.60054(19) 0.31228(10) 0.3670(3) 0.0361(4) Uani 1 1 d . . . N4 N 0.46974(19) 0.33791(10) 0.1577(3) 0.0361(4) Uani 1 1 d . . . N5 N 0.5047(2) 0.39424(10) -0.0113(3) 0.0379(4) Uani 1 1 d . . . N6 N 0.7593(2) 0.47239(11) -0.0023(4) 0.0424(4) Uani 1 1 d . . . O7 O 0.7028(2) 0.48972(10) -0.2501(3) 0.0569(5) Uani 1 1 d . . . O8 O 0.8768(2) 0.50689(10) 0.1676(4) 0.0595(5) Uani 1 1 d . . . N9 N 0.9046(2) 0.34314(10) 0.5198(4) 0.0379(4) Uani 1 1 d . . . O10 O 0.91706(19) 0.32074(10) 0.7574(3) 0.0544(5) Uani 1 1 d . . . O11 O 1.02512(19) 0.35491(10) 0.4253(3) 0.0547(5) Uani 1 1 d . . . N12 N 0.3055(2) 0.30497(12) 0.1206(4) 0.0476(5) Uani 1 1 d D . . H12A H 0.279(3) 0.2813(16) -0.039(3) 0.071 Uiso 1 1 d D . . H12B H 0.238(3) 0.3466(11) 0.106(6) 0.071 Uiso 1 1 d 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 0.0364(10) 0.0318(10) 0.0354(11) -0.0025(8) 0.0137(8) 0.0027(8) C2 0.0324(10) 0.0330(10) 0.0328(11) -0.0034(8) 0.0086(8) 0.0004(8) N3 0.0355(9) 0.0356(9) 0.0365(9) -0.0006(7) 0.0093(7) 0.0012(7) N4 0.0304(9) 0.0378(9) 0.0394(10) -0.0006(7) 0.0090(7) 0.0011(7) N5 0.0380(9) 0.0392(9) 0.0368(9) 0.0029(7) 0.0114(7) 0.0044(7) N6 0.0465(10) 0.0352(9) 0.0520(12) 0.0024(9) 0.0245(9) 0.0051(8) O7 0.0742(11) 0.0555(10) 0.0477(10) 0.0157(8) 0.0285(9) 0.0108(8) O8 0.0563(10) 0.0544(10) 0.0698(12) -0.0061(8) 0.0218(9) -0.0191(8) N9 0.0363(10) 0.0342(9) 0.0403(11) -0.0025(7) 0.0066(8) 0.0009(7) O10 0.0511(9) 0.0607(10) 0.0432(9) 0.0130(8) 0.0011(7) -0.0015(7) O11 0.0362(8) 0.0677(11) 0.0614(11) -0.0057(8) 0.0164(7) -0.0002(7) N12 0.0322(9) 0.0542(12) 0.0547(12) 0.0000(9) 0.0103(9) -0.0048(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 C1 N5 1.316(2) . ? C1 C2 1.379(3) . ? C1 N6 1.451(3) . ? C2 N3 1.319(2) . ? C2 N9 1.442(2) . ? N3 N4 1.313(2) . ? N4 N5 1.325(2) . ? N4 N12 1.385(2) . ? N6 O8 1.205(2) . ? N6 O7 1.219(2) . ? N9 O11 1.212(2) . ? N9 O10 1.217(2) . ? N12 H12A 0.853(10) . ? N12 H12B 0.854(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 N5 C1 C2 109.36(17) . . ? N5 C1 N6 119.66(17) . . ? C2 C1 N6 130.50(18) . . ? N3 C2 C1 109.16(16) . . ? N3 C2 N9 119.86(17) . . ? C1 C2 N9 130.92(18) . . ? N4 N3 C2 102.41(16) . . ? N3 N4 N5 116.92(15) . . ? N3 N4 N12 119.69(17) . . ? N5 N4 N12 123.39(16) . . ? C1 N5 N4 102.15(15) . . ? O8 N6 O7 126.22(19) . . ? O8 N6 C1 116.47(18) . . ? O7 N6 C1 117.25(18) . . ? O11 N9 O10 125.56(17) . . ? O11 N9 C2 117.14(17) . . ? O10 N9 C2 117.30(17) . . ? N4 N12 H12A 104.9(18) . . ? N4 N12 H12B 105.8(18) . . ? H12A N12 H12B 107(3) . . ? 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 N5 C1 C2 N3 -0.3(2) . . . . ? N6 C1 C2 N3 171.56(19) . . . . ? N5 C1 C2 N9 176.69(18) . . . . ? N6 C1 C2 N9 -11.4(3) . . . . ? C1 C2 N3 N4 -0.09(19) . . . . ? N9 C2 N3 N4 -177.48(15) . . . . ? C2 N3 N4 N5 0.5(2) . . . . ? C2 N3 N4 N12 179.57(17) . . . . ? C2 C1 N5 N4 0.56(19) . . . . ? N6 C1 N5 N4 -172.34(16) . . . . ? N3 N4 N5 C1 -0.7(2) . . . . ? N12 N4 N5 C1 -179.72(17) . . . . ? N5 C1 N6 O8 145.88(19) . . . . ? C2 C1 N6 O8 -25.3(3) . . . . ? N5 C1 N6 O7 -31.6(3) . . . . ? C2 C1 N6 O7 157.26(19) . . . . ? N3 C2 N9 O11 149.86(18) . . . . ? C1 C2 N9 O11 -26.9(3) . . . . ? N3 C2 N9 O10 -29.5(2) . . . . ? C1 C2 N9 O10 153.8(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N12 H12A N12 0.853(10) 2.253(13) 3.063(2) 158(2) 4_565 _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 26.25 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.159 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.048