# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 #TrackingRef 'shrv72-final.cif' #=========================================================================== _audit_creation_date 2009-04-09 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _audit_update_record ; ; #=========================================================================== # 1. SUBMISSION DETAILS #=========================================================================== _publ_contact_author_name 'Dr Damon A. Parrish' _publ_contact_author_address ; Laboratory for the Structure of Matter Naval Research Laboratory Washington, DC 20375 ; _publ_contact_author_email damon.parrish@nrl.navy.mil _publ_contact_author_fax 202-767-6874 _publ_contact_author_phone 202-404-2141 _publ_requested_category ? _publ_requested_coeditor_name ? _publ_contact_letter ; ; #=========================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) # Do NOT alter anthing in this section. #=========================================================================== _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #=========================================================================== # 3. TITLE AND AUTHOR LIST #=========================================================================== _publ_section_title ; title ; loop_ _publ_author_name _publ_author_address _publ_author_footnote D.A.Parrish ; Laboratory for the Structure of Matter, Code 6030 Naval Research Laboratory Washington, DC 20375 ; ? J.Shreeve ; Chemsitry Department University of Idaho Moscow, ID, 83843 ; ? Y.-H.Joo ; Chemsitry Department University of Idaho Moscow, ID, 83843 ; ? #=========================================================================== # 4. TEXT #=========================================================================== _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; ; _publ_section_references ; Bruker (2006). APEX2 v2.1-0. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2005). SAINT v7.34A. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2004). SADABS v2004/1, Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2004). XPREP v2005/2. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2000b). SHELXTL v6.12. Bruker AXS Inc., Madison, Wisconsin, USA. ; _publ_section_figure_captions ; ; _publ_section_table_legends ; ; _publ_section_acknowledgements ; Crystallographic studies were supported in part by the Office of Naval Research (ONR) and the Naval Research Laboratory (NRL). ; #========================================================================== data_shrv72 _database_code_depnum_ccdc_archive 'CCDC 861469' #TrackingRef 'shrv72-final.cif' _audit_creation_date 2009-04-09 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; (E)-2-(5-(nitroimino)-4,5-dihydro-1H-tetrazol-1-yl)acetic acid hydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C3 H4 N6 O4, H2 O1' _chemical_formula_sum 'C3 H6 N6 O5' _chemical_formula_weight 206.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 23.1690(14) _cell_length_b 8.6022(5) _cell_length_c 8.0337(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1601.15(17) _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 prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.53 _exptl_crystal_size_min 0.49 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.710 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.159 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2004/1 (Bruker, 2004)' _exptl_absorpt_correction_T_min 0.833 _exptl_absorpt_correction_T_max 1.000 _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16419 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0113 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 28.29 _reflns_number_total 1996 _reflns_number_gt 1816 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2 v2.1-0 (Bruker, 2006)' _computing_cell_refinement 'Bruker APEX2 v2.1-0 (Bruker, 2006)' _computing_data_reduction ; Bruker SAINT v7.34A (Bruker, 2005), Bruker XPREP v2005/2 (Bruker, 2004) ; _computing_structure_solution 'Bruker SHELXTL v6.12 (Bruker, 2000b)' _computing_structure_refinement 'Bruker SHELXTL v6.12 (Bruker, 2000b)' _computing_molecular_graphics 'Bruker SHELXTL v6.12 (Bruker, 2000b)' _computing_publication_material 'Bruker SHELXTL v6.12 (Bruker, 2000b)' _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^)+(0.0513P)^2^+0.4460P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.044(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1996 _refine_ls_number_parameters 140 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0360 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.0954 _refine_ls_wR_factor_gt 0.0927 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.031 _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 N1 N 0.35681(4) 0.64477(11) 0.14752(12) 0.0321(2) Uani 1 1 d . . . N2 N 0.37877(4) 0.50345(12) 0.18520(14) 0.0396(3) Uani 1 1 d . . . N3 N 0.41973(5) 0.52394(12) 0.28856(14) 0.0405(3) Uani 1 1 d . . . N4 N 0.42449(4) 0.67803(11) 0.32068(13) 0.0343(2) Uani 1 1 d . . . H4 H 0.4490 0.7193 0.3879 0.041 Uiso 1 1 calc R . . C5 C 0.38523(4) 0.75623(13) 0.23172(13) 0.0301(2) Uani 1 1 d . . . C6 C 0.30537(5) 0.66301(14) 0.04633(14) 0.0334(2) Uani 1 1 d . . . H6A H 0.3056 0.5870 -0.0428 0.040 Uiso 1 1 calc R . . H6B H 0.3050 0.7658 -0.0032 0.040 Uiso 1 1 calc R . . C7 C 0.25204(5) 0.64121(13) 0.15221(14) 0.0330(2) Uani 1 1 d . . . O8 O 0.20566(4) 0.68968(13) 0.07367(13) 0.0499(3) Uani 1 1 d D . . O9 O 0.25287(4) 0.58660(13) 0.28867(11) 0.0504(3) Uani 1 1 d . . . N10 N 0.37047(4) 0.90495(11) 0.20929(13) 0.0357(2) Uani 1 1 d . . . N11 N 0.40288(4) 1.00820(12) 0.29062(13) 0.0370(2) Uani 1 1 d . . . O12 O 0.39001(4) 1.14681(10) 0.26878(14) 0.0494(3) Uani 1 1 d . . . O13 O 0.44353(4) 0.97048(11) 0.38227(14) 0.0529(3) Uani 1 1 d . . . O1S O 0.51225(4) 0.72368(12) 0.52662(14) 0.0523(3) Uani 1 1 d D . . H1SA H 0.5272(8) 0.6577(18) 0.589(2) 0.071(6) Uiso 1 1 d D . . H1SB H 0.5224(8) 0.8122(14) 0.560(2) 0.068(6) Uiso 1 1 d D . . H8 H 0.1768(6) 0.664(2) 0.131(2) 0.075(6) 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 N1 0.0279(4) 0.0303(5) 0.0382(5) -0.0021(4) -0.0031(4) -0.0012(3) N2 0.0385(5) 0.0306(5) 0.0497(6) -0.0017(4) -0.0065(4) 0.0005(4) N3 0.0402(5) 0.0305(5) 0.0509(6) 0.0001(4) -0.0086(4) 0.0018(4) N4 0.0319(5) 0.0304(5) 0.0404(5) -0.0012(4) -0.0074(4) 0.0003(4) C5 0.0248(5) 0.0325(5) 0.0331(5) -0.0015(4) -0.0006(4) -0.0009(4) C6 0.0280(5) 0.0404(6) 0.0319(5) -0.0014(4) -0.0037(4) -0.0031(4) C7 0.0311(5) 0.0330(5) 0.0348(5) -0.0027(4) -0.0016(4) -0.0018(4) O8 0.0286(4) 0.0713(7) 0.0497(5) 0.0175(5) 0.0010(4) 0.0021(4) O9 0.0443(5) 0.0679(7) 0.0389(5) 0.0118(4) 0.0023(4) 0.0042(5) N10 0.0312(5) 0.0290(5) 0.0470(6) -0.0024(4) -0.0093(4) 0.0001(4) N11 0.0326(5) 0.0304(5) 0.0479(6) -0.0033(4) -0.0082(4) 0.0009(4) O12 0.0461(5) 0.0268(4) 0.0752(7) -0.0030(4) -0.0195(5) 0.0019(4) O13 0.0497(5) 0.0366(5) 0.0725(7) -0.0067(4) -0.0315(5) 0.0044(4) O1S 0.0509(6) 0.0412(5) 0.0650(7) -0.0018(5) -0.0287(5) -0.0001(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C5 1.3455(14) . ? N1 N2 1.3521(14) . ? N1 C6 1.4512(14) . ? N2 N3 1.2734(14) . ? N3 N4 1.3550(14) . ? N4 C5 1.3382(14) . ? N4 H4 0.8600 . ? C5 N10 1.3365(15) . ? C6 C7 1.5117(16) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 O9 1.1929(14) . ? C7 O8 1.3140(14) . ? O8 H8 0.841(9) . ? N10 N11 1.3340(14) . ? N11 O13 1.2388(13) . ? N11 O12 1.2415(14) . ? O1S H1SA 0.833(9) . ? O1S H1SB 0.842(9) . ? 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 C5 N1 N2 110.12(9) . . ? C5 N1 C6 127.34(10) . . ? N2 N1 C6 122.11(9) . . ? N3 N2 N1 107.58(10) . . ? N2 N3 N4 108.68(10) . . ? C5 N4 N3 109.56(9) . . ? C5 N4 H4 125.2 . . ? N3 N4 H4 125.2 . . ? N10 C5 N4 136.64(10) . . ? N10 C5 N1 119.29(10) . . ? N4 C5 N1 104.06(9) . . ? N1 C6 C7 110.04(9) . . ? N1 C6 H6A 109.7 . . ? C7 C6 H6A 109.7 . . ? N1 C6 H6B 109.7 . . ? C7 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? O9 C7 O8 125.41(11) . . ? O9 C7 C6 123.56(11) . . ? O8 C7 C6 111.03(9) . . ? C7 O8 H8 107.8(14) . . ? N11 N10 C5 115.30(9) . . ? O13 N11 O12 121.21(10) . . ? O13 N11 N10 123.00(10) . . ? O12 N11 N10 115.79(10) . . ? H1SA O1S H1SB 107.8(18) . . ? 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 C5 N1 N2 N3 -0.32(13) . . . . ? C6 N1 N2 N3 -173.32(10) . . . . ? N1 N2 N3 N4 0.67(13) . . . . ? N2 N3 N4 C5 -0.79(14) . . . . ? N3 N4 C5 N10 -178.29(13) . . . . ? N3 N4 C5 N1 0.56(12) . . . . ? N2 N1 C5 N10 178.94(10) . . . . ? C6 N1 C5 N10 -8.53(17) . . . . ? N2 N1 C5 N4 -0.16(12) . . . . ? C6 N1 C5 N4 172.38(10) . . . . ? C5 N1 C6 C7 -89.82(13) . . . . ? N2 N1 C6 C7 81.90(13) . . . . ? N1 C6 C7 O9 -13.86(16) . . . . ? N1 C6 C7 O8 166.30(10) . . . . ? N4 C5 N10 N11 2.2(2) . . . . ? N1 C5 N10 N11 -176.52(10) . . . . ? C5 N10 N11 O13 -0.73(17) . . . . ? C5 N10 N11 O12 179.05(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 N4 H4 O1S 0.86 1.84 2.6506(13) 156.0 . O1S H1SA N3 0.833(9) 2.218(10) 3.0372(14) 167.8(19) 5_666 O1S H1SB O13 0.842(9) 2.080(10) 2.9166(14) 171.9(19) 5_676 O8 H8 O12 0.841(9) 1.910(10) 2.7398(13) 168.9(19) 8_655 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.284 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.039 # Attachment 'shrv77-final.cif' data_shrv77 _database_code_depnum_ccdc_archive 'CCDC 861470' #TrackingRef 'shrv77-final.cif' _audit_creation_date 2009-09-28 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; 2-(1H-tetrazol-1-yl)acetic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C3 H4 N4 O2' _chemical_formula_sum 'C3 H4 N4 O2' _chemical_formula_weight 128.10 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 12.4884(7) _cell_length_b 5.0947(3) _cell_length_c 17.4942(10) _cell_angle_alpha 90.00 _cell_angle_beta 99.9410(10) _cell_angle_gamma 90.00 _cell_volume 1096.35(11) _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 'thick needle' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.552 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.132 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.6774 _exptl_absorpt_correction_T_max 0.7454 _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 8688 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0171 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2252 _reflns_number_gt 1873 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2 v2009.3-0 (Bruker, 2006)' _computing_cell_refinement 'Bruker APEX2 v2009.3-0 (Bruker, 2006)' _computing_data_reduction ; Bruker SAINT v7.60A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008) ; _computing_structure_solution 'Bruker SHELXTL v6.12 (Bruker, 2000b)' _computing_structure_refinement 'Bruker SHELXTL v6.12 (Bruker, 2000b)' _computing_molecular_graphics 'Bruker SHELXTL v6.12 (Bruker, 2000b)' _computing_publication_material 'Bruker SHELXTL v6.12 (Bruker, 2000b)' _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^)+(0.0420P)^2^+0.2884P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2252 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.0891 _refine_ls_wR_factor_gt 0.0835 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 N1A N -0.73305(10) 0.1783(3) 0.09501(8) 0.0550(4) Uani 1 1 d . . . N2A N -0.67875(10) 0.0900(3) 0.04017(7) 0.0462(3) Uani 1 1 d . . . N3A N -0.58588(9) 0.2061(3) 0.04409(7) 0.0427(3) Uani 1 1 d . . . N4A N -0.57924(8) 0.3753(2) 0.10288(6) 0.0300(3) Uani 1 1 d . . . C5A C -0.66853(11) 0.3539(4) 0.13349(9) 0.0471(4) Uani 1 1 d . . . H5AA H -0.6833 0.4489 0.1759 0.056 Uiso 1 1 calc R . . C6A C -0.48095(10) 0.5260(3) 0.12893(7) 0.0339(3) Uani 1 1 d . . . H6AA H -0.4997 0.6919 0.1505 0.041 Uiso 1 1 calc R . . H6AB H -0.4452 0.5633 0.0851 0.041 Uiso 1 1 calc R . . C7A C -0.40443(10) 0.3748(3) 0.18986(7) 0.0326(3) Uani 1 1 d . . . O8A O -0.31618(7) 0.5110(2) 0.21328(6) 0.0469(3) Uani 1 1 d . . . H8AA H -0.2753 0.4273 0.2462 0.070 Uiso 1 1 calc R . . O9A O -0.42460(8) 0.1613(2) 0.21253(6) 0.0519(3) Uani 1 1 d . . . N1B N -0.15594(9) 0.2377(3) 0.29995(7) 0.0402(3) Uani 1 1 d . . . N2B N -0.12316(10) 0.0172(3) 0.26686(7) 0.0462(3) Uani 1 1 d . . . N3B N -0.02632(10) -0.0451(3) 0.29936(7) 0.0425(3) Uani 1 1 d . . . N4B N 0.00493(8) 0.1358(2) 0.35501(6) 0.0309(3) Uani 1 1 d . . . C5B C -0.07526(10) 0.3068(3) 0.35427(8) 0.0332(3) Uani 1 1 d . . . H5BA H -0.0743 0.4513 0.3868 0.040 Uiso 1 1 calc R . . C6B C 0.11508(10) 0.1357(3) 0.39893(9) 0.0374(3) Uani 1 1 d . . . H6BA H 0.1227 0.2780 0.4363 0.045 Uiso 1 1 calc R . . H6BB H 0.1660 0.1662 0.3638 0.045 Uiso 1 1 calc R . . C7B C 0.14248(11) -0.1206(3) 0.44110(8) 0.0347(3) Uani 1 1 d . . . O8B O 0.24887(8) -0.1533(2) 0.45555(7) 0.0515(3) Uani 1 1 d . . . H8BA H 0.2634 -0.2928 0.4784 0.077 Uiso 1 1 calc R . . O9B O 0.07721(8) -0.2696(2) 0.45967(6) 0.0474(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1A 0.0432(7) 0.0707(10) 0.0509(8) -0.0114(7) 0.0070(6) -0.0223(7) N2A 0.0457(7) 0.0426(7) 0.0462(7) -0.0094(6) -0.0037(5) -0.0098(6) N3A 0.0412(7) 0.0462(7) 0.0388(6) -0.0128(6) 0.0019(5) -0.0035(6) N4A 0.0277(5) 0.0319(6) 0.0280(5) -0.0018(4) -0.0016(4) -0.0021(4) C5A 0.0346(7) 0.0636(11) 0.0438(8) -0.0161(7) 0.0093(6) -0.0111(7) C6A 0.0306(6) 0.0361(8) 0.0326(7) 0.0035(6) -0.0013(5) -0.0069(6) C7A 0.0277(6) 0.0380(8) 0.0308(6) -0.0001(6) 0.0015(5) -0.0010(6) O8A 0.0319(5) 0.0510(7) 0.0512(6) 0.0056(5) -0.0112(4) -0.0062(5) O9A 0.0445(6) 0.0461(7) 0.0591(7) 0.0190(5) -0.0075(5) -0.0050(5) N1B 0.0282(6) 0.0466(8) 0.0436(7) -0.0012(6) -0.0004(5) 0.0008(5) N2B 0.0409(7) 0.0473(8) 0.0464(7) -0.0082(6) -0.0035(5) -0.0046(6) N3B 0.0434(7) 0.0364(7) 0.0454(7) -0.0087(6) 0.0010(5) 0.0008(5) N4B 0.0285(5) 0.0278(6) 0.0344(6) -0.0001(5) 0.0004(4) 0.0012(4) C5B 0.0286(6) 0.0336(7) 0.0363(7) 0.0000(6) 0.0024(5) 0.0022(5) C6B 0.0284(7) 0.0298(7) 0.0500(8) 0.0053(6) -0.0042(6) 0.0009(5) C7B 0.0356(7) 0.0291(7) 0.0363(7) -0.0011(6) -0.0027(5) 0.0019(6) O8B 0.0353(5) 0.0416(6) 0.0724(7) 0.0196(5) -0.0054(5) 0.0057(5) O9B 0.0447(6) 0.0383(6) 0.0570(7) 0.0117(5) 0.0024(5) -0.0035(5) _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 C5A 1.3096(19) . ? N1A N2A 1.3444(19) . ? N2A N3A 1.2931(17) . ? N3A N4A 1.3335(16) . ? N4A C5A 1.3222(17) . ? N4A C6A 1.4530(16) . ? C5A H5AA 0.9300 . ? C6A C7A 1.5136(17) . ? C6A H6AA 0.9700 . ? C6A H6AB 0.9700 . ? C7A O9A 1.1993(17) . ? C7A O8A 1.3068(16) . ? O8A H8AA 0.8200 . ? N1B C5B 1.3082(17) . ? N1B N2B 1.3587(18) . ? N2B N3B 1.2844(17) . ? N3B N4B 1.3487(16) . ? N4B C5B 1.3255(17) . ? N4B C6B 1.4552(16) . ? C5B H5BA 0.9300 . ? C6B C7B 1.5096(19) . ? C6B H6BA 0.9700 . ? C6B H6BB 0.9700 . ? C7B O9B 1.1990(17) . ? C7B O8B 1.3195(16) . ? O8B H8BA 0.8200 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5A N1A N2A 104.71(12) . . ? N3A N2A N1A 111.56(12) . . ? N2A N3A N4A 105.79(11) . . ? C5A N4A N3A 108.34(11) . . ? C5A N4A C6A 129.97(12) . . ? N3A N4A C6A 121.35(11) . . ? N1A C5A N4A 109.58(13) . . ? N1A C5A H5AA 125.2 . . ? N4A C5A H5AA 125.2 . . ? N4A C6A C7A 110.39(11) . . ? N4A C6A H6AA 109.6 . . ? C7A C6A H6AA 109.6 . . ? N4A C6A H6AB 109.6 . . ? C7A C6A H6AB 109.6 . . ? H6AA C6A H6AB 108.1 . . ? O9A C7A O8A 126.27(12) . . ? O9A C7A C6A 123.46(12) . . ? O8A C7A C6A 110.27(12) . . ? C7A O8A H8AA 109.5 . . ? C5B N1B N2B 106.32(11) . . ? N3B N2B N1B 110.24(11) . . ? N2B N3B N4B 106.46(11) . . ? C5B N4B N3B 108.55(11) . . ? C5B N4B C6B 130.48(12) . . ? N3B N4B C6B 120.67(11) . . ? N1B C5B N4B 108.43(12) . . ? N1B C5B H5BA 125.8 . . ? N4B C5B H5BA 125.8 . . ? N4B C6B C7B 111.86(11) . . ? N4B C6B H6BA 109.2 . . ? C7B C6B H6BA 109.2 . . ? N4B C6B H6BB 109.2 . . ? C7B C6B H6BB 109.2 . . ? H6BA C6B H6BB 107.9 . . ? O9B C7B O8B 125.26(13) . . ? O9B C7B C6B 124.93(12) . . ? O8B C7B C6B 109.80(12) . . ? C7B O8B H8BA 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5A N1A N2A N3A -0.46(19) . . . . ? N1A N2A N3A N4A -0.16(17) . . . . ? N2A N3A N4A C5A 0.72(16) . . . . ? N2A N3A N4A C6A 174.64(12) . . . . ? N2A N1A C5A N4A 0.90(19) . . . . ? N3A N4A C5A N1A -1.04(18) . . . . ? C6A N4A C5A N1A -174.26(13) . . . . ? C5A N4A C6A C7A 83.85(18) . . . . ? N3A N4A C6A C7A -88.61(15) . . . . ? N4A C6A C7A O9A -0.32(19) . . . . ? N4A C6A C7A O8A -179.89(11) . . . . ? C5B N1B N2B N3B -0.29(16) . . . . ? N1B N2B N3B N4B 0.40(16) . . . . ? N2B N3B N4B C5B -0.36(15) . . . . ? N2B N3B N4B C6B -174.73(12) . . . . ? N2B N1B C5B N4B 0.05(15) . . . . ? N3B N4B C5B N1B 0.19(15) . . . . ? C6B N4B C5B N1B 173.82(13) . . . . ? C5B N4B C6B C7B 128.40(15) . . . . ? N3B N4B C6B C7B -58.63(17) . . . . ? N4B C6B C7B O9B -24.1(2) . . . . ? N4B C6B C7B O8B 157.02(12) . . . . ? 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 O8A H8AA N1B 0.82 1.89 2.6822(15) 163.6 . O8B H8BA N2A 0.82 1.93 2.7382(16) 169.8 4_656 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.153 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.036 # Attachment 'shrv125-final.cif' data_shrv125 _database_code_depnum_ccdc_archive 'CCDC 861471' #TrackingRef 'shrv125-final.cif' _audit_creation_date 2010-08-12 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; bis(4-amino-4H-1,2,4-triazol-1-ium) ((E)-4-(carboxylatomethyl)-5- (nitroimino)-4,5-dihydrotetrazol-1-ide) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C2 H5 N4 1+), C3 H2 N6 O4 1-' _chemical_formula_sum 'C7 H12 N14 O4' _chemical_formula_weight 356.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.4438(8) _cell_length_b 16.020(2) _cell_length_c 17.071(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.374(2) _cell_angle_gamma 90.00 _cell_volume 1487.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.591 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.132 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.9404 _exptl_absorpt_correction_T_max 0.9960 _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 12677 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 25.87 _reflns_number_total 2842 _reflns_number_gt 2250 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2 v2009.3-0 (Bruker, 2009)' _computing_cell_refinement 'Bruker APEX2 v2009.3-0 (Bruker, 2009)' _computing_data_reduction ; Bruker SAINT v7.60A (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^)+(0.0490P)^2^+0.3000P] 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 2842 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0968 _refine_ls_wR_factor_gt 0.0890 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 N1 N -0.2053(2) 0.93042(8) 0.28325(7) 0.0341(3) Uani 1 1 d . . . N2 N -0.3157(3) 0.97015(9) 0.34153(8) 0.0437(4) Uani 1 1 d . . . N3 N -0.2022(3) 0.94749(9) 0.40556(8) 0.0463(4) Uani 1 1 d . . . N4 N -0.0161(3) 0.89299(8) 0.39124(7) 0.0395(3) Uani 1 1 d . . . C5 C -0.0197(3) 0.88390(9) 0.31372(8) 0.0311(3) Uani 1 1 d . . . C6 C -0.2758(3) 0.94180(10) 0.20153(9) 0.0391(4) Uani 1 1 d . . . H6A H -0.4294 0.9725 0.1976 0.047 Uiso 1 1 calc R . . H6B H -0.3036 0.8875 0.1776 0.047 Uiso 1 1 calc R . . C7 C -0.0843(3) 0.98827(10) 0.15658(9) 0.0379(4) Uani 1 1 d . . . O8 O -0.0921(3) 0.98193(9) 0.08508(7) 0.0647(4) Uani 1 1 d . . . O9 O 0.0684(2) 1.03222(8) 0.19631(6) 0.0503(3) Uani 1 1 d . . . N10 N 0.1137(2) 0.84060(8) 0.26088(7) 0.0375(3) Uani 1 1 d . . . N11 N 0.3090(2) 0.80118(8) 0.28993(8) 0.0384(3) Uani 1 1 d . . . O12 O 0.3708(2) 0.80155(8) 0.36084(7) 0.0551(4) Uani 1 1 d . . . O13 O 0.4347(2) 0.76281(8) 0.24139(8) 0.0549(4) Uani 1 1 d . . . N14A N -0.1200(3) 0.65555(8) 0.46865(8) 0.0421(3) Uani 1 1 d . . . C15A C -0.1916(3) 0.68154(11) 0.39628(11) 0.0470(4) Uani 1 1 d . . . H15A H -0.3295 0.7143 0.3850 0.056 Uiso 1 1 calc R . . N16A N -0.0432(3) 0.65489(9) 0.34422(9) 0.0499(4) Uani 1 1 d . . . N17A N 0.1312(3) 0.61021(9) 0.38673(8) 0.0453(4) Uani 1 1 d . . . H17A H 0.2547 0.5855 0.3671 0.054 Uiso 1 1 calc R . . C18A C 0.0841(3) 0.61039(10) 0.46036(10) 0.0443(4) Uani 1 1 d . . . H18A H 0.1755 0.5839 0.5003 0.053 Uiso 1 1 calc R . . N19A N -0.2510(4) 0.67311(13) 0.53647(11) 0.0629(5) Uani 1 1 d . . . H19A H -0.305(5) 0.6208(15) 0.5545(13) 0.075 Uiso 1 1 d . . . H19B H -0.141(5) 0.6930(15) 0.5748(14) 0.075 Uiso 1 1 d . . . N14B N -0.5354(2) 1.14075(8) 0.38493(7) 0.0350(3) Uani 1 1 d . . . C15B C -0.3565(3) 1.19283(11) 0.36239(9) 0.0452(4) Uani 1 1 d . . . H15B H -0.3501 1.2164 0.3127 0.054 Uiso 1 1 calc R . . N16B N -0.1947(3) 1.20566(10) 0.41904(8) 0.0510(4) Uani 1 1 d . . . N17B N -0.2763(3) 1.15840(9) 0.47890(7) 0.0442(4) Uani 1 1 d . . . H17B H -0.2028 1.1543 0.5243 0.053 Uiso 1 1 calc R . . C18B C -0.4789(3) 1.12043(10) 0.45855(9) 0.0415(4) Uani 1 1 d . . . H18B H -0.5685 1.0853 0.4900 0.050 Uiso 1 1 calc R . . N19B N -0.7417(3) 1.10843(12) 0.34299(9) 0.0507(4) Uani 1 1 d . . . H19C H -0.806(4) 1.1488(14) 0.3175(12) 0.061 Uiso 1 1 d . . . H19D H -0.693(4) 1.0711(13) 0.3140(12) 0.061 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 N1 0.0357(7) 0.0379(7) 0.0288(6) 0.0057(5) 0.0044(5) 0.0068(6) N2 0.0454(9) 0.0450(8) 0.0415(8) 0.0056(6) 0.0126(6) 0.0114(7) N3 0.0544(10) 0.0510(9) 0.0345(7) 0.0027(6) 0.0119(7) 0.0116(7) N4 0.0465(9) 0.0438(8) 0.0282(6) 0.0022(6) 0.0024(6) 0.0081(6) C5 0.0342(9) 0.0320(7) 0.0270(7) 0.0034(6) 0.0009(6) 0.0013(6) C6 0.0378(9) 0.0447(9) 0.0341(8) 0.0068(7) -0.0058(7) 0.0009(7) C7 0.0458(10) 0.0392(8) 0.0282(8) 0.0029(6) -0.0029(7) -0.0017(7) O8 0.0842(11) 0.0842(10) 0.0255(6) -0.0033(6) 0.0009(6) -0.0267(8) O9 0.0600(8) 0.0568(7) 0.0336(6) 0.0009(5) -0.0047(6) -0.0199(6) N10 0.0389(8) 0.0426(7) 0.0307(7) -0.0022(6) -0.0004(6) 0.0101(6) N11 0.0359(8) 0.0348(7) 0.0446(8) -0.0059(6) 0.0016(6) 0.0020(6) O12 0.0513(8) 0.0667(8) 0.0459(7) -0.0069(6) -0.0139(6) 0.0215(7) O13 0.0450(8) 0.0533(8) 0.0672(8) -0.0198(6) 0.0122(6) 0.0103(6) N14A 0.0371(8) 0.0403(8) 0.0487(8) -0.0020(6) -0.0004(6) 0.0023(6) C15A 0.0395(10) 0.0429(9) 0.0579(11) 0.0059(8) -0.0075(9) 0.0075(8) N16A 0.0464(9) 0.0500(9) 0.0525(9) 0.0052(7) -0.0071(7) 0.0072(7) N17A 0.0402(9) 0.0435(8) 0.0516(9) -0.0036(7) -0.0048(7) 0.0106(6) C18A 0.0419(10) 0.0419(9) 0.0482(10) -0.0005(8) -0.0091(8) 0.0056(8) N19A 0.0547(11) 0.0752(12) 0.0595(11) -0.0030(9) 0.0098(9) 0.0073(10) N14B 0.0409(8) 0.0368(7) 0.0276(6) -0.0002(5) 0.0037(5) 0.0049(6) C15B 0.0517(11) 0.0536(10) 0.0303(8) 0.0096(7) 0.0026(7) -0.0030(9) N16B 0.0550(10) 0.0609(10) 0.0371(8) 0.0072(7) 0.0013(7) -0.0090(8) N17B 0.0536(9) 0.0520(8) 0.0266(6) 0.0024(6) -0.0016(6) 0.0045(7) C18B 0.0516(11) 0.0431(9) 0.0301(8) 0.0056(7) 0.0071(7) 0.0024(8) N19B 0.0472(10) 0.0559(10) 0.0482(9) -0.0046(7) -0.0058(7) 0.0010(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 N1 C5 1.3428(19) . ? N1 N2 1.3439(18) . ? N1 C6 1.4429(18) . ? N2 N3 1.285(2) . ? N3 N4 1.3671(19) . ? N4 C5 1.3307(19) . ? C5 N10 1.3697(19) . ? C6 C7 1.515(2) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 O8 1.2239(19) . ? C7 O9 1.2649(19) . ? N10 N11 1.3159(19) . ? N11 O12 1.2428(17) . ? N11 O13 1.2569(17) . ? N14A C18A 1.338(2) . ? N14A C15A 1.346(2) . ? N14A N19A 1.413(2) . ? C15A N16A 1.298(2) . ? C15A H15A 0.9300 . ? N16A N17A 1.3724(19) . ? N17A C18A 1.293(2) . ? N17A H17A 0.8600 . ? C18A H18A 0.9300 . ? N19A H19A 0.94(2) . ? N19A H19B 0.93(2) . ? N14B C18B 1.3221(19) . ? N14B C15B 1.350(2) . ? N14B N19B 1.406(2) . ? C15B N16B 1.297(2) . ? C15B H15B 0.9300 . ? N16B N17B 1.3609(19) . ? N17B C18B 1.295(2) . ? N17B H17B 0.8600 . ? C18B H18B 0.9300 . ? N19B H19C 0.85(2) . ? N19B H19D 0.83(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 C5 N1 N2 109.18(12) . . ? C5 N1 C6 127.62(13) . . ? N2 N1 C6 123.14(13) . . ? N3 N2 N1 106.37(13) . . ? N2 N3 N4 111.21(12) . . ? C5 N4 N3 105.51(12) . . ? N4 C5 N1 107.71(13) . . ? N4 C5 N10 136.39(14) . . ? N1 C5 N10 115.89(12) . . ? N1 C6 C7 112.98(13) . . ? N1 C6 H6A 109.0 . . ? C7 C6 H6A 109.0 . . ? N1 C6 H6B 109.0 . . ? C7 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? O8 C7 O9 125.17(16) . . ? O8 C7 C6 117.89(15) . . ? O9 C7 C6 116.91(13) . . ? N11 N10 C5 115.90(12) . . ? O12 N11 O13 120.77(14) . . ? O12 N11 N10 123.14(13) . . ? O13 N11 N10 116.08(13) . . ? C18A N14A C15A 106.27(15) . . ? C18A N14A N19A 130.08(15) . . ? C15A N14A N19A 123.62(15) . . ? N16A C15A N14A 111.23(15) . . ? N16A C15A H15A 124.4 . . ? N14A C15A H15A 124.4 . . ? C15A N16A N17A 104.24(14) . . ? C18A N17A N16A 110.62(15) . . ? C18A N17A H17A 124.7 . . ? N16A N17A H17A 124.7 . . ? N17A C18A N14A 107.63(15) . . ? N17A C18A H18A 126.2 . . ? N14A C18A H18A 126.2 . . ? N14A N19A H19A 105.3(14) . . ? N14A N19A H19B 108.2(15) . . ? H19A N19A H19B 106(2) . . ? C18B N14B C15B 106.32(14) . . ? C18B N14B N19B 122.88(14) . . ? C15B N14B N19B 130.76(14) . . ? N16B C15B N14B 111.15(14) . . ? N16B C15B H15B 124.4 . . ? N14B C15B H15B 124.4 . . ? C15B N16B N17B 103.84(15) . . ? C18B N17B N16B 111.15(14) . . ? C18B N17B H17B 124.4 . . ? N16B N17B H17B 124.4 . . ? N17B C18B N14B 107.54(14) . . ? N17B C18B H18B 126.2 . . ? N14B C18B H18B 126.2 . . ? N14B N19B H19C 106.7(15) . . ? N14B N19B H19D 107.4(16) . . ? H19C N19B H19D 113(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 C5 N1 N2 N3 -0.78(17) . . . . ? C6 N1 N2 N3 -178.00(14) . . . . ? N1 N2 N3 N4 0.08(18) . . . . ? N2 N3 N4 C5 0.63(19) . . . . ? N3 N4 C5 N1 -1.09(17) . . . . ? N3 N4 C5 N10 179.03(18) . . . . ? N2 N1 C5 N4 1.18(17) . . . . ? C6 N1 C5 N4 178.25(14) . . . . ? N2 N1 C5 N10 -178.90(13) . . . . ? C6 N1 C5 N10 -1.8(2) . . . . ? C5 N1 C6 C7 -66.4(2) . . . . ? N2 N1 C6 C7 110.28(17) . . . . ? N1 C6 C7 O8 160.71(16) . . . . ? N1 C6 C7 O9 -20.8(2) . . . . ? N4 C5 N10 N11 -6.1(3) . . . . ? N1 C5 N10 N11 173.99(13) . . . . ? C5 N10 N11 O12 0.8(2) . . . . ? C5 N10 N11 O13 -178.58(13) . . . . ? C18A N14A C15A N16A 0.0(2) . . . . ? N19A N14A C15A N16A -178.04(17) . . . . ? N14A C15A N16A N17A -0.3(2) . . . . ? C15A N16A N17A C18A 0.58(19) . . . . ? N16A N17A C18A N14A -0.59(19) . . . . ? C15A N14A C18A N17A 0.36(19) . . . . ? N19A N14A C18A N17A 178.23(18) . . . . ? C18B N14B C15B N16B -0.5(2) . . . . ? N19B N14B C15B N16B -178.33(16) . . . . ? N14B C15B N16B N17B 0.8(2) . . . . ? C15B N16B N17B C18B -0.85(19) . . . . ? N16B N17B C18B N14B 0.58(19) . . . . ? C15B N14B C18B N17B -0.08(18) . . . . ? N19B N14B C18B N17B 177.99(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 N17A H17A O9 0.86 1.71 2.5370(19) 161.4 2_545 N19A H19A O8 0.94(2) 2.34(3) 3.230(3) 156(2) 4_576 N19A H19B N16B 0.93(2) 2.44(2) 3.176(3) 136.1(19) 3_576 N17B H17B N4 0.86 1.98 2.7988(19) 158.1 3_576 N19B H19C O13 0.85(2) 2.19(2) 3.028(2) 172(2) 2_455 N19B H19D O9 0.83(2) 2.43(2) 2.935(2) 120.2(18) 1_455 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.87 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.223 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.037