# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_shrv235 _audit_creation_date 2013-04-05 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; di(2H-tetrazol-5-yl)methanone oxime DMSO ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C3 H3 N9 O1, C2 H6 O1 S1' _chemical_formula_sum 'C5 H9 N9 O2 S' _chemical_formula_weight 259.27 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.3993(9) _cell_length_b 10.477(2) _cell_length_c 12.184(3) _cell_angle_alpha 68.811(3) _cell_angle_beta 84.903(3) _cell_angle_gamma 89.122(3) _cell_volume 521.49(19) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.651 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.321 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.6752 _exptl_absorpt_correction_T_max 0.7458 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 5676 _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 29.18 _reflns_number_total 2709 _reflns_number_gt 2165 _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^)+(0.0475P)^2^+0.1387P] 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 2709 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0514 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.0975 _refine_ls_wR_factor_gt 0.0905 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 1.0178(3) 0.23566(14) 1.08369(12) 0.0179(3) Uani 1 1 d . . . H1 H 0.8910 0.2962 1.0954 0.021 Uiso 1 1 calc R . . N2 N 1.1913(3) 0.15179(15) 1.16377(13) 0.0207(3) Uani 1 1 d . . . N3 N 1.3441(3) 0.07940(15) 1.11106(12) 0.0208(3) Uani 1 1 d . . . N4 N 1.2747(3) 0.11388(15) 0.99853(12) 0.0193(3) Uani 1 1 d . . . C5 C 1.0702(4) 0.21158(17) 0.98263(14) 0.0167(3) Uani 1 1 d . . . C6 C 0.9396(4) 0.27845(17) 0.86990(14) 0.0174(3) Uani 1 1 d . . . N7 N 0.7489(3) 0.37739(15) 0.84542(12) 0.0198(3) Uani 1 1 d . . . O8 O 0.6620(3) 0.41573(13) 0.93934(10) 0.0241(3) Uani 1 1 d . . . H8 H 0.5505 0.4846 0.9174 0.036 Uiso 1 1 calc R . . C9 C 1.0323(4) 0.23421(17) 0.77037(14) 0.0173(3) Uani 1 1 d . . . N10 N 1.2371(3) 0.13864(15) 0.76867(12) 0.0193(3) Uani 1 1 d . . . H10 H 1.3399 0.0900 0.8282 0.023 Uiso 1 1 calc R . . N11 N 1.2595(4) 0.12933(16) 0.66123(13) 0.0232(3) Uani 1 1 d . . . N12 N 1.0715(4) 0.21750(16) 0.60006(13) 0.0258(3) Uani 1 1 d . . . N13 N 0.9243(4) 0.28481(16) 0.66523(13) 0.0235(3) Uani 1 1 d . . . S1' S 1.49154(9) 0.33076(4) 1.31085(4) 0.01871(12) Uani 1 1 d . . . O2' O 1.6599(3) 0.38498(13) 1.18670(10) 0.0227(3) Uani 1 1 d . . . C3' C 1.6584(4) 0.17015(18) 1.38417(15) 0.0239(4) Uani 1 1 d . . . H3'A H 1.6063 0.1052 1.3474 0.036 Uiso 1 1 calc R . . H3'B H 1.5801 0.1351 1.4677 0.036 Uiso 1 1 calc R . . H3'C H 1.8807 0.1817 1.3779 0.036 Uiso 1 1 calc R . . C4' C 1.6414(4) 0.42871(19) 1.38718(15) 0.0241(4) Uani 1 1 d . . . H4'A H 1.5572 0.5209 1.3592 0.036 Uiso 1 1 calc R . . H4'B H 1.8643 0.4348 1.3722 0.036 Uiso 1 1 calc R . . H4'C H 1.5852 0.3843 1.4722 0.036 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0193(7) 0.0183(7) 0.0176(7) -0.0083(6) -0.0032(5) 0.0058(5) N2 0.0214(7) 0.0222(7) 0.0202(7) -0.0093(6) -0.0050(5) 0.0068(6) N3 0.0216(7) 0.0240(8) 0.0189(7) -0.0101(6) -0.0044(5) 0.0065(6) N4 0.0214(7) 0.0205(7) 0.0170(7) -0.0078(6) -0.0037(5) 0.0059(6) C5 0.0173(8) 0.0170(8) 0.0173(7) -0.0082(6) -0.0012(6) 0.0013(6) C6 0.0191(8) 0.0176(8) 0.0169(7) -0.0079(6) -0.0019(6) 0.0026(6) N7 0.0242(7) 0.0209(7) 0.0170(7) -0.0102(6) -0.0021(5) 0.0054(6) O8 0.0305(7) 0.0254(7) 0.0194(6) -0.0116(5) -0.0040(5) 0.0142(5) C9 0.0186(8) 0.0156(8) 0.0184(8) -0.0072(6) -0.0017(6) 0.0014(6) N10 0.0233(7) 0.0203(7) 0.0166(7) -0.0091(6) -0.0035(5) 0.0051(6) N11 0.0292(8) 0.0249(8) 0.0192(7) -0.0125(6) -0.0024(6) 0.0044(6) N12 0.0334(9) 0.0266(8) 0.0218(7) -0.0132(6) -0.0063(6) 0.0061(7) N13 0.0298(8) 0.0247(8) 0.0200(7) -0.0122(6) -0.0060(6) 0.0063(6) S1' 0.0206(2) 0.0205(2) 0.0181(2) -0.01055(16) -0.00288(15) 0.00414(15) O2' 0.0294(7) 0.0229(6) 0.0169(6) -0.0092(5) -0.0017(5) 0.0097(5) C3' 0.0329(10) 0.0190(9) 0.0206(8) -0.0084(7) -0.0013(7) 0.0038(7) C4' 0.0314(10) 0.0228(9) 0.0225(8) -0.0130(7) -0.0053(7) 0.0037(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 N2 1.3413(19) . ? N1 C5 1.344(2) . ? N1 H1 0.8800 . ? N2 N3 1.3037(19) . ? N3 N4 1.3478(19) . ? N4 C5 1.324(2) . ? C5 C6 1.463(2) . ? C6 N7 1.289(2) . ? C6 C9 1.471(2) . ? N7 O8 1.3663(17) . ? O8 H8 0.8400 . ? C9 N13 1.326(2) . ? C9 N10 1.341(2) . ? N10 N11 1.3424(19) . ? N10 H10 0.8800 . ? N11 N12 1.297(2) . ? N12 N13 1.359(2) . ? S1' O2' 1.5336(13) . ? S1' C3' 1.7778(18) . ? S1' C4' 1.7812(18) . ? C3' H3'A 0.9800 . ? C3' H3'B 0.9800 . ? C3' H3'C 0.9800 . ? C4' H4'A 0.9800 . ? C4' H4'B 0.9800 . ? C4' H4'C 0.9800 . ? 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 N2 N1 C5 108.48(13) . . ? N2 N1 H1 125.8 . . ? C5 N1 H1 125.8 . . ? N3 N2 N1 106.14(13) . . ? N2 N3 N4 111.23(13) . . ? C5 N4 N3 105.68(13) . . ? N4 C5 N1 108.47(14) . . ? N4 C5 C6 122.60(14) . . ? N1 C5 C6 128.93(15) . . ? N7 C6 C5 126.71(15) . . ? N7 C6 C9 114.07(14) . . ? C5 C6 C9 119.22(14) . . ? C6 N7 O8 113.25(14) . . ? N7 O8 H8 109.5 . . ? N13 C9 N10 108.36(14) . . ? N13 C9 C6 124.61(15) . . ? N10 C9 C6 127.04(15) . . ? C9 N10 N11 108.81(13) . . ? C9 N10 H10 125.6 . . ? N11 N10 H10 125.6 . . ? N12 N11 N10 106.19(13) . . ? N11 N12 N13 111.19(14) . . ? C9 N13 N12 105.45(14) . . ? O2' S1' C3' 105.16(8) . . ? O2' S1' C4' 105.19(8) . . ? C3' S1' C4' 99.80(9) . . ? S1' C3' H3'A 109.5 . . ? S1' C3' H3'B 109.5 . . ? H3'A C3' H3'B 109.5 . . ? S1' C3' H3'C 109.5 . . ? H3'A C3' H3'C 109.5 . . ? H3'B C3' H3'C 109.5 . . ? S1' C4' H4'A 109.5 . . ? S1' C4' H4'B 109.5 . . ? H4'A C4' H4'B 109.5 . . ? S1' C4' H4'C 109.5 . . ? H4'A C4' H4'C 109.5 . . ? H4'B C4' H4'C 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 C5 N1 N2 N3 0.06(19) . . . . ? N1 N2 N3 N4 -0.01(19) . . . . ? N2 N3 N4 C5 -0.1(2) . . . . ? N3 N4 C5 N1 0.09(19) . . . . ? N3 N4 C5 C6 179.01(15) . . . . ? N2 N1 C5 N4 -0.10(19) . . . . ? N2 N1 C5 C6 -178.93(17) . . . . ? N4 C5 C6 N7 -177.24(17) . . . . ? N1 C5 C6 N7 1.4(3) . . . . ? N4 C5 C6 C9 1.4(3) . . . . ? N1 C5 C6 C9 -179.95(16) . . . . ? C5 C6 N7 O8 -2.2(3) . . . . ? C9 C6 N7 O8 179.08(14) . . . . ? N7 C6 C9 N13 -2.9(3) . . . . ? C5 C6 C9 N13 178.32(16) . . . . ? N7 C6 C9 N10 176.67(16) . . . . ? C5 C6 C9 N10 -2.1(3) . . . . ? N13 C9 N10 N11 0.3(2) . . . . ? C6 C9 N10 N11 -179.33(16) . . . . ? C9 N10 N11 N12 -0.07(19) . . . . ? N10 N11 N12 N13 -0.2(2) . . . . ? N10 C9 N13 N12 -0.38(19) . . . . ? C6 C9 N13 N12 179.25(16) . . . . ? N11 N12 N13 C9 0.3(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 N1 H1 O2' 0.88 1.91 2.7377(18) 155.7 1_455 O8 H8 O2' 0.84 1.80 2.5886(16) 155.1 2_767 N10 H10 N3 0.88 2.19 2.948(2) 144.3 2_857 _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 29.18 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.349 _refine_diff_density_min -0.425 _refine_diff_density_rms 0.062 _database_code_depnum_ccdc_archive 'CCDC 953372' ####################################################################### # # 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_shrv241 _audit_creation_date 2013-05-24 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; 5,5'-(hydrazonomethylene)bis(1H-tetrazole) hydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C3 H4 N10, H2 O1' _chemical_formula_sum 'C3 H6 N10 O1' _chemical_formula_weight 198.18 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 4.7217(4) _cell_length_b 16.4748(14) _cell_length_c 10.3658(9) _cell_angle_alpha 90.00 _cell_angle_beta 101.975(2) _cell_angle_gamma 90.00 _cell_volume 788.80(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(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 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.669 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.135 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.9800 _exptl_absorpt_correction_T_max 0.9840 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 7413 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0151 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 26.49 _reflns_number_total 1611 _reflns_number_gt 1488 _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^)+(0.0455P)^2^+0.4147P] 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 0.0033(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1611 _refine_ls_number_parameters 134 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0898 _refine_ls_wR_factor_gt 0.0871 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4077(3) 0.63052(8) 0.30354(12) 0.0149(3) Uani 1 1 d . . . C2 C 0.2736(3) 0.69099(8) 0.37453(13) 0.0152(3) Uani 1 1 d . . . N3 N 0.2976(2) 0.77083(7) 0.36122(11) 0.0179(3) Uani 1 1 d . . . N4 N 0.1376(3) 0.80462(7) 0.44181(12) 0.0188(3) Uani 1 1 d . . . N5 N 0.0216(3) 0.74907(7) 0.50280(11) 0.0181(3) Uani 1 1 d . . . N6 N 0.1054(2) 0.67745(7) 0.46250(11) 0.0157(3) Uani 1 1 d . . . H6 H 0.0584 0.6295 0.4891 0.019 Uiso 1 1 calc R . . C7 C 0.3539(3) 0.54497(8) 0.32437(12) 0.0154(3) Uani 1 1 d . . . N8 N 0.1790(3) 0.51699(6) 0.39829(12) 0.0183(3) Uani 1 1 d . . . N9 N 0.1949(3) 0.43477(7) 0.39080(11) 0.0198(3) Uani 1 1 d . . . N10 N 0.3704(3) 0.41289(7) 0.31588(11) 0.0200(3) Uani 1 1 d . . . N11 N 0.4730(3) 0.48200(6) 0.27361(11) 0.0171(3) Uani 1 1 d . . . H11 H 0.5975 0.4852 0.2213 0.021 Uiso 1 1 calc R . . N12 N 0.5759(2) 0.64679(7) 0.22118(11) 0.0166(3) Uani 1 1 d . . . N13 N 0.6408(2) 0.72185(7) 0.19662(11) 0.0180(3) Uani 1 1 d . . . H13A H 0.5709 0.7623 0.2358 0.022 Uiso 1 1 calc R . . H13B H 0.7542 0.7317 0.1410 0.022 Uiso 1 1 calc R . . O1S O 0.2207(2) 0.52708(6) 0.93348(11) 0.0244(3) Uani 1 1 d D . . H1SA H 0.195(4) 0.5758(2) 0.9425(19) 0.037 Uiso 1 1 d D . . H1SB H 0.368(2) 0.5091(12) 0.9810(16) 0.037 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 0.0169(6) 0.0129(6) 0.0162(6) 0.0003(5) 0.0063(5) -0.0002(5) C2 0.0154(6) 0.0155(6) 0.0154(6) 0.0000(5) 0.0048(5) -0.0010(5) N3 0.0210(6) 0.0139(6) 0.0208(6) 0.0000(4) 0.0091(5) -0.0006(4) N4 0.0216(6) 0.0154(6) 0.0216(6) -0.0008(4) 0.0094(5) -0.0005(4) N5 0.0206(6) 0.0150(5) 0.0204(6) -0.0007(4) 0.0082(5) 0.0010(4) N6 0.0190(6) 0.0120(5) 0.0181(6) 0.0000(4) 0.0082(4) -0.0007(4) C7 0.0173(6) 0.0138(6) 0.0158(6) 0.0000(5) 0.0049(5) 0.0003(5) N8 0.0236(6) 0.0120(6) 0.0219(6) 0.0011(4) 0.0104(5) -0.0014(4) N9 0.0250(6) 0.0142(6) 0.0223(6) 0.0004(4) 0.0098(5) -0.0014(4) N10 0.0249(6) 0.0143(6) 0.0227(6) 0.0007(4) 0.0093(5) -0.0007(5) N11 0.0210(6) 0.0127(5) 0.0201(6) 0.0006(4) 0.0098(5) -0.0006(4) N12 0.0178(6) 0.0158(6) 0.0174(5) 0.0014(4) 0.0061(4) -0.0004(4) N13 0.0218(6) 0.0148(6) 0.0206(6) 0.0018(4) 0.0114(5) -0.0027(4) O1S 0.0313(6) 0.0142(5) 0.0305(6) 0.0019(4) 0.0126(5) 0.0041(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 C1 N12 1.3085(17) . ? C1 C7 1.4562(18) . ? C1 C2 1.4588(18) . ? C2 N3 1.3299(17) . ? C2 N6 1.3462(17) . ? N3 N4 1.3564(16) . ? N4 N5 1.2965(16) . ? N5 N6 1.3386(15) . ? N6 H6 0.8800 . ? C7 N8 1.3207(17) . ? C7 N11 1.3387(17) . ? N8 N9 1.3596(16) . ? N9 N10 1.2986(16) . ? N10 N11 1.3457(15) . ? N11 H11 0.8800 . ? N12 N13 1.3116(15) . ? N13 H13A 0.8800 . ? N13 H13B 0.8800 . ? O1S H1SA 0.82000(18) . ? O1S H1SB 0.82000(12) . ? 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 N12 C1 C7 116.30(12) . . ? N12 C1 C2 125.09(12) . . ? C7 C1 C2 118.60(12) . . ? N3 C2 N6 108.00(11) . . ? N3 C2 C1 124.61(12) . . ? N6 C2 C1 127.39(12) . . ? C2 N3 N4 105.78(11) . . ? N5 N4 N3 110.86(11) . . ? N4 N5 N6 106.74(11) . . ? N5 N6 C2 108.63(11) . . ? N5 N6 H6 125.7 . . ? C2 N6 H6 125.7 . . ? N8 C7 N11 108.77(12) . . ? N8 C7 C1 124.98(12) . . ? N11 C7 C1 126.26(12) . . ? C7 N8 N9 105.42(11) . . ? N10 N9 N8 111.13(11) . . ? N9 N10 N11 106.10(11) . . ? C7 N11 N10 108.59(11) . . ? C7 N11 H11 125.7 . . ? N10 N11 H11 125.7 . . ? C1 N12 N13 121.16(11) . . ? N12 N13 H13A 120.0 . . ? N12 N13 H13B 120.0 . . ? H13A N13 H13B 120.0 . . ? H1SA O1S H1SB 114(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 N12 C1 C2 N3 2.3(2) . . . . ? C7 C1 C2 N3 -177.72(12) . . . . ? N12 C1 C2 N6 -178.20(13) . . . . ? C7 C1 C2 N6 1.7(2) . . . . ? N6 C2 N3 N4 -0.69(14) . . . . ? C1 C2 N3 N4 178.85(12) . . . . ? C2 N3 N4 N5 0.40(14) . . . . ? N3 N4 N5 N6 0.06(14) . . . . ? N4 N5 N6 C2 -0.49(14) . . . . ? N3 C2 N6 N5 0.75(15) . . . . ? C1 C2 N6 N5 -178.78(12) . . . . ? N12 C1 C7 N8 -176.36(12) . . . . ? C2 C1 C7 N8 3.7(2) . . . . ? N12 C1 C7 N11 4.2(2) . . . . ? C2 C1 C7 N11 -175.72(12) . . . . ? N11 C7 N8 N9 -0.09(14) . . . . ? C1 C7 N8 N9 -179.59(12) . . . . ? C7 N8 N9 N10 -0.11(15) . . . . ? N8 N9 N10 N11 0.25(15) . . . . ? N8 C7 N11 N10 0.25(15) . . . . ? C1 C7 N11 N10 179.74(12) . . . . ? N9 N10 N11 C7 -0.30(14) . . . . ? C7 C1 N12 N13 -179.21(11) . . . . ? C2 C1 N12 N13 0.7(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 N6 H6 N9 0.88 2.17 2.9389(16) 145.2 3_566 N11 H11 O1S 0.88 1.98 2.8302(16) 161.7 3_666 N13 H13A N3 0.88 2.02 2.7084(16) 134.5 . N13 H13B N5 0.88 2.12 3.0000(16) 177.6 4_675 O1S H1SA N4 0.82 1.988(3) 2.8041(15) 173.1(19) 4_576 O1S H1SB O1S 0.82 2.049(5) 2.854(2) 167(2) 3_667 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.49 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.431 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 953373' ####################################################################### # # 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_shrv245 _audit_creation_date 2013-07-22 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; dihydroxylammonium (5,5'-(hydrazonomethylene)ditetrazol-2-ide) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(H4 N1 O1 +1), C3 H2 N10' _chemical_formula_sum 'C3 H10 N12 O2' _chemical_formula_weight 246.23 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 6.5633(11) _cell_length_b 7.6976(13) _cell_length_c 19.158(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 967.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.690 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.141 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.9737 _exptl_absorpt_correction_T_max 0.9972 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 8823 _diffrn_reflns_av_R_equivalents 0.0421 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 26.57 _reflns_number_total 1993 _reflns_number_gt 1829 _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^)+(0.0459P)^2^+0.4097P] 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(2) _refine_ls_number_reflns 1993 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.0964 _refine_ls_wR_factor_gt 0.0932 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 N1 N 0.0776(3) 0.0243(2) 1.03437(9) 0.0177(4) Uani 1 1 d . . . N2 N 0.0821(3) 0.0477(2) 1.10413(9) 0.0169(4) Uani 1 1 d . . . N3 N 0.0619(3) 0.2131(2) 1.11828(9) 0.0179(4) Uani 1 1 d . . . N4 N 0.0443(3) 0.3024(2) 1.05830(9) 0.0162(4) Uani 1 1 d . . . C5 C 0.0557(3) 0.1837(3) 1.00760(10) 0.0143(4) Uani 1 1 d . . . C6 C 0.0525(3) 0.2222(3) 0.93225(10) 0.0147(4) Uani 1 1 d . . . C7 C 0.0454(3) 0.0755(3) 0.88295(10) 0.0159(4) Uani 1 1 d . . . N8 N 0.1374(3) 0.0714(3) 0.82048(10) 0.0280(5) Uani 1 1 d . . . N9 N 0.1001(4) -0.0890(3) 0.79529(10) 0.0342(6) Uani 1 1 d . . . N10 N -0.0103(3) -0.1763(3) 0.84059(10) 0.0277(5) Uani 1 1 d . . . N11 N -0.0452(3) -0.0763(2) 0.89640(9) 0.0216(4) Uani 1 1 d . . . N12 N 0.0608(3) 0.3857(2) 0.91542(8) 0.0175(4) Uani 1 1 d . . . N13 N 0.0632(3) 0.4323(3) 0.84777(9) 0.0229(4) Uani 1 1 d . . . H13A H 0.0591 0.3522 0.8150 0.027 Uiso 1 1 calc R . . H13B H 0.0688 0.5428 0.8363 0.027 Uiso 1 1 calc R . . O1S O 0.0903(3) 0.4210(3) 1.23991(10) 0.0416(5) Uani 1 1 d . . . H1S H 0.1260 0.3665 1.2039 0.062 Uiso 1 1 calc R . . N2S N -0.0614(4) 0.3247(3) 1.27593(10) 0.0246(4) Uani 1 1 d . . . H2SA H -0.087(4) 0.373(3) 1.3210(14) 0.030 Uiso 1 1 d . . . H2SB H -0.028(5) 0.225(4) 1.2862(13) 0.030 Uiso 1 1 d . . . H2SC H -0.192(4) 0.333(4) 1.2481(14) 0.030 Uiso 1 1 d . . . O3S O -0.0320(2) -0.3588(2) 1.06089(9) 0.0250(4) Uani 1 1 d . . . H3S H -0.0385 -0.4648 1.0709 0.038 Uiso 1 1 calc R . . N4S N 0.1350(3) -0.3297(3) 1.01505(10) 0.0188(4) Uani 1 1 d . . . H4SA H 0.128(4) -0.227(4) 1.0061(14) 0.023 Uiso 1 1 d . . . H4SB H 0.123(4) -0.414(3) 0.9739(13) 0.023 Uiso 1 1 d . . . H4SC H 0.250(4) -0.369(3) 1.0368(13) 0.023 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 0.0239(10) 0.0162(8) 0.0130(8) 0.0007(7) 0.0004(8) 0.0013(8) N2 0.0201(10) 0.0177(9) 0.0128(8) -0.0004(7) 0.0014(7) -0.0004(8) N3 0.0207(10) 0.0178(9) 0.0153(9) 0.0001(7) 0.0011(8) -0.0010(8) N4 0.0181(8) 0.0157(9) 0.0149(8) 0.0007(7) -0.0005(8) 0.0005(8) C5 0.0119(9) 0.0141(10) 0.0170(9) -0.0001(8) 0.0015(9) -0.0010(9) C6 0.0106(9) 0.0179(10) 0.0155(10) 0.0014(8) 0.0003(9) 0.0013(8) C7 0.0146(9) 0.0199(10) 0.0132(9) 0.0022(8) 0.0003(9) 0.0003(9) N8 0.0419(13) 0.0269(11) 0.0152(10) -0.0029(9) 0.0071(9) -0.0040(9) N9 0.0580(16) 0.0258(11) 0.0189(10) -0.0037(8) 0.0064(10) -0.0053(11) N10 0.0398(13) 0.0259(10) 0.0175(10) -0.0043(8) -0.0006(8) -0.0033(10) N11 0.0266(10) 0.0208(9) 0.0174(9) -0.0028(8) 0.0013(8) -0.0048(9) N12 0.0165(8) 0.0196(9) 0.0163(9) 0.0023(7) 0.0022(8) 0.0009(8) N13 0.0313(11) 0.0217(9) 0.0157(9) 0.0057(7) 0.0004(9) 0.0024(9) O1S 0.0399(12) 0.0476(12) 0.0372(11) 0.0025(9) 0.0044(9) 0.0017(10) N2S 0.0365(12) 0.0190(10) 0.0183(10) 0.0013(8) -0.0016(9) 0.0016(10) O3S 0.0227(8) 0.0176(7) 0.0347(9) 0.0026(7) 0.0083(8) 0.0000(7) N4S 0.0200(9) 0.0159(10) 0.0204(10) 0.0013(8) -0.0013(8) 0.0019(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 1.337(3) . ? N1 N2 1.349(2) . ? N2 N3 1.309(3) . ? N3 N4 1.344(2) . ? N4 C5 1.336(3) . ? C5 C6 1.474(3) . ? C6 N12 1.300(3) . ? C6 C7 1.473(3) . ? C7 N11 1.336(3) . ? C7 N8 1.341(3) . ? N8 N9 1.348(3) . ? N9 N10 1.316(3) . ? N10 N11 1.337(3) . ? N12 N13 1.345(2) . ? N13 H13A 0.8800 . ? N13 H13B 0.8800 . ? O1S N2S 1.420(3) . ? O1S H1S 0.8400 . ? N2S H2SA 0.96(3) . ? N2S H2SB 0.82(3) . ? N2S H2SC 1.01(3) . ? O3S N4S 1.423(2) . ? O3S H3S 0.8400 . ? N4S H4SA 0.81(3) . ? N4S H4SB 1.02(3) . ? N4S H4SC 0.91(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 C5 N1 N2 105.07(17) . . ? N3 N2 N1 109.44(16) . . ? N2 N3 N4 109.21(16) . . ? C5 N4 N3 105.51(16) . . ? N4 C5 N1 110.77(18) . . ? N4 C5 C6 125.03(18) . . ? N1 C5 C6 124.16(18) . . ? N12 C6 C7 125.74(18) . . ? N12 C6 C5 115.91(18) . . ? C7 C6 C5 118.33(17) . . ? N11 C7 N8 110.63(19) . . ? N11 C7 C6 124.10(18) . . ? N8 C7 C6 125.2(2) . . ? C7 N8 N9 105.0(2) . . ? N10 N9 N8 109.39(18) . . ? N9 N10 N11 109.11(19) . . ? C7 N11 N10 105.84(17) . . ? C6 N12 N13 119.85(18) . . ? N12 N13 H13A 120.0 . . ? N12 N13 H13B 120.0 . . ? H13A N13 H13B 120.0 . . ? N2S O1S H1S 109.5 . . ? O1S N2S H2SA 111.2(17) . . ? O1S N2S H2SB 115(2) . . ? H2SA N2S H2SB 101(2) . . ? O1S N2S H2SC 107.9(15) . . ? H2SA N2S H2SC 107(2) . . ? H2SB N2S H2SC 114(3) . . ? N4S O3S H3S 109.5 . . ? O3S N4S H4SA 103.8(19) . . ? O3S N4S H4SB 108.4(14) . . ? H4SA N4S H4SB 117(2) . . ? O3S N4S H4SC 107.6(16) . . ? H4SA N4S H4SC 118(2) . . ? H4SB N4S H4SC 102(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 0.6(3) . . . . ? N1 N2 N3 N4 -0.2(3) . . . . ? N2 N3 N4 C5 -0.3(2) . . . . ? N3 N4 C5 N1 0.7(2) . . . . ? N3 N4 C5 C6 -177.2(2) . . . . ? N2 N1 C5 N4 -0.8(3) . . . . ? N2 N1 C5 C6 177.1(2) . . . . ? N4 C5 C6 N12 7.5(3) . . . . ? N1 C5 C6 N12 -170.0(2) . . . . ? N4 C5 C6 C7 -173.88(19) . . . . ? N1 C5 C6 C7 8.6(3) . . . . ? N12 C6 C7 N11 -150.6(2) . . . . ? C5 C6 C7 N11 31.0(3) . . . . ? N12 C6 C7 N8 33.4(3) . . . . ? C5 C6 C7 N8 -145.1(2) . . . . ? N11 C7 N8 N9 0.2(3) . . . . ? C6 C7 N8 N9 176.7(2) . . . . ? C7 N8 N9 N10 0.3(3) . . . . ? N8 N9 N10 N11 -0.8(3) . . . . ? N8 C7 N11 N10 -0.7(3) . . . . ? C6 C7 N11 N10 -177.2(2) . . . . ? N9 N10 N11 C7 0.9(3) . . . . ? C7 C6 N12 N13 0.1(3) . . . . ? C5 C6 N12 N13 178.56(19) . . . . ? 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 N13 H13A N8 0.88 2.22 2.868(3) 129.8 . N13 H13B N10 0.88 2.23 3.055(3) 157.0 1_565 O1S H1S N3 0.84 2.07 2.833(3) 151.7 . N2S H2SA N2 0.96(3) 1.97(3) 2.871(3) 157(2) 3_557 N2S H2SB O1S 0.82(3) 2.42(3) 3.128(3) 144(3) 3_547 N2S H2SC N8 1.01(3) 1.88(3) 2.821(3) 154(2) 2_457 O3S H3S N4 0.84 1.89 2.657(2) 151.5 1_545 N4S H4SA N1 0.81(3) 2.04(3) 2.776(3) 152(3) . N4S H4SB N12 1.02(3) 1.95(3) 2.946(3) 164(2) 1_545 N4S H4SC N11 0.91(3) 1.90(3) 2.794(3) 164(2) 2_547 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.57 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.265 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 953374'