# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (C) The Royal Society of Chemistry 2008 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _publ_contact_author_name 'T M Klapotke' _publ_contact_author_email TMK@CUP.UNI-MUENCHEN.DE _publ_section_title ; Bistetrazolylamines - Synthesis and Characterization ; _publ_author_name 'T M Klapotke' # Attachment 'jn404_H2bta_H2O.cif' data_jn404 _database_code_depnum_ccdc_archive 'CCDC 299051' _audit_creation_method SHELXL-97 _audit_creation_date 04-Oct-05 _audit_update_record ? _chemical_name_systematic 'N,N-Bis(1H-tetrazol-5-yl)amine monohydrate' _chemical_compound_source ? _chemical_name_common 'N,N-Bis(1H-tetrazol-5-yl)amine monohydrate' _chemical_formula_moiety 'C2 H3 N9, H2 O' _chemical_formula_sum 'C2 H5 N9 O' _chemical_formula_weight 171.15 _diffrn_ambient_temperature 200 # in K _diffrn_source_type 'Spellman generator' _diffrn_source_power 2.250 # in kW _diffrn_source_voltage 50.00 _diffrn_source_current 45.00 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source ? _diffrn_radiation_monochromator 'vertically mounted graphite crystal' _diffrn_radiation_collimation 0.5 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method omega-scan _diffrn_radiation_type 'Mo K\a' _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 2966 _diffrn_reflns_av_R_equivalents 0.0187 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 27.41 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.41 _diffrn_measured_fraction_theta_full 0.997 _reflns_number_total 1529 _reflns_number_gt 1257 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.1107044 _diffrn_orient_matrix_UB_12 -0.0009879 _diffrn_orient_matrix_UB_13 0.0707465 _diffrn_orient_matrix_UB_21 -0.0963909 _diffrn_orient_matrix_UB_22 -0.0064597 _diffrn_orient_matrix_UB_23 0.0797176 _diffrn_orient_matrix_UB_31 0.0054181 _diffrn_orient_matrix_UB_32 -0.0947362 _diffrn_orient_matrix_UB_33 -0.0061734 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2ybc' 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' 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 9.3669(19) _cell_length_b 10.531(2) _cell_length_c 6.8081(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.42(3) _cell_angle_gamma 90.00 _cell_volume 671.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 1612 _cell_measurement_theta_min 3.134 _cell_measurement_theta_max 27.485 _cell_special_details ? _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.693 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.140 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 -1 0.015000 0 0 1 0.025000 0 1 0 0.090000 0 -1 0 0.060000 1 0 0 0.040000 -1 0 0 0.060000 7 6 0 0.050000 3 -4 0 0.050000 _diffrn_special_details ? _refine_diff_density_max 0.193 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.044 _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid # Plot Program for Crystal Structure Illustrations, Oak Ridge National # Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ. # Glasgow) used --- SCHAKAL (E. Keller, University of Freiburg (Breisgau), # Germany, 1995)' ; _computing_publication_material ;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version). # --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses). ; _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 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1529 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0464 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.0998 _refine_ls_wR_factor_gt 0.0935 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 O1 O 0.76925(13) -0.36372(12) 0.1447(3) 0.0655(4) Uani 1 1 d . . . H3 H 0.8646(19) -0.0562(18) 0.068(3) 0.050(5) Uiso 1 1 d . . . H2 H 0.663(2) 0.2364(19) 0.148(3) 0.058(6) Uiso 1 1 d . . . H4 H 0.725(2) -0.435(2) 0.148(3) 0.069(6) Uiso 1 1 d . . . H1 H 0.675(2) -0.2287(19) 0.174(3) 0.051(5) Uiso 1 1 d . . . H5 H 0.865(3) -0.370(2) 0.086(3) 0.077(7) Uiso 1 1 d . . . N9 N 0.96644(11) 0.16361(11) 0.00915(17) 0.0305(3) Uani 1 1 d . . . N4 N 0.45721(11) -0.02916(11) 0.27051(18) 0.0353(3) Uani 1 1 d . . . N2 N 0.62741(12) -0.15102(11) 0.18944(18) 0.0326(3) Uani 1 1 d . . . N1 N 0.80225(11) 0.00337(11) 0.10081(18) 0.0320(3) Uani 1 1 d . . . N8 N 0.96000(11) 0.29295(11) 0.00495(18) 0.0327(3) Uani 1 1 d . . . C2 C 0.83997(12) 0.12670(13) 0.07307(18) 0.0265(3) Uani 1 1 d . . . N6 N 0.75907(12) 0.22912(10) 0.10590(17) 0.0293(3) Uani 1 1 d . . . N3 N 0.49195(12) -0.14738(11) 0.25663(19) 0.0355(3) Uani 1 1 d . . . N7 N 0.83757(12) 0.33358(11) 0.06183(17) 0.0338(3) Uani 1 1 d . . . N5 N 0.56644(11) 0.04745(11) 0.21457(17) 0.0328(3) Uani 1 1 d . . . C1 C 0.66991(12) -0.03146(13) 0.16620(19) 0.0282(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 O1 0.0323(6) 0.0279(6) 0.1368(13) 0.0063(7) 0.0296(7) -0.0011(4) N9 0.0220(5) 0.0284(6) 0.0413(6) 0.0006(5) 0.0087(4) -0.0019(4) N4 0.0242(5) 0.0299(6) 0.0519(7) 0.0017(5) 0.0133(5) -0.0010(4) N2 0.0222(5) 0.0259(6) 0.0499(7) 0.0028(5) 0.0106(5) 0.0014(4) N1 0.0205(5) 0.0249(6) 0.0507(7) -0.0009(5) 0.0129(4) 0.0010(4) N8 0.0250(6) 0.0290(6) 0.0443(6) 0.0010(5) 0.0089(5) -0.0009(4) C2 0.0206(6) 0.0270(6) 0.0320(7) -0.0005(5) 0.0058(5) -0.0003(4) N6 0.0221(5) 0.0251(6) 0.0407(6) -0.0006(4) 0.0083(4) -0.0002(4) N3 0.0229(5) 0.0295(6) 0.0542(7) 0.0035(5) 0.0120(5) -0.0007(4) N7 0.0262(6) 0.0300(6) 0.0454(7) 0.0016(5) 0.0087(5) -0.0019(4) N5 0.0222(5) 0.0278(6) 0.0484(7) 0.0004(5) 0.0118(4) -0.0009(4) C1 0.0210(6) 0.0272(6) 0.0365(7) 0.0007(5) 0.0069(5) -0.0005(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 H4 0.86(2) . ? O1 H5 0.99(2) . ? N9 C2 1.3234(16) . ? N9 N8 1.3636(15) . ? N4 N3 1.2904(16) . ? N4 N5 1.3596(15) . ? N2 C1 1.3302(17) . ? N2 N3 1.3525(16) . ? N2 H1 0.94(2) . ? N1 C2 1.3595(18) . ? N1 C1 1.3702(16) . ? N1 H3 0.886(19) . ? N8 N7 1.2863(16) . ? C2 N6 1.3378(17) . ? N6 N7 1.3579(15) . ? N6 H2 0.95(2) . ? N5 C1 1.3203(17) . ? 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 H4 O1 H5 113.3(19) . . ? C2 N9 N8 105.11(10) . . ? N3 N4 N5 111.17(10) . . ? C1 N2 N3 107.20(10) . . ? C1 N2 H1 132.1(11) . . ? N3 N2 H1 120.6(11) . . ? C2 N1 C1 122.51(11) . . ? C2 N1 H3 118.0(12) . . ? C1 N1 H3 119.4(12) . . ? N7 N8 N9 111.43(10) . . ? N9 C2 N6 109.13(12) . . ? N9 C2 N1 124.08(12) . . ? N6 C2 N1 126.79(11) . . ? C2 N6 N7 107.93(10) . . ? C2 N6 H2 130.9(12) . . ? N7 N6 H2 121.1(12) . . ? N4 N3 N2 106.85(10) . . ? N8 N7 N6 106.40(10) . . ? C1 N5 N4 104.58(11) . . ? N5 C1 N2 110.19(11) . . ? N5 C1 N1 125.46(12) . . ? N2 C1 N1 124.35(11) . . ? 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 C2 N9 N8 N7 -0.20(14) . . . . ? N8 N9 C2 N6 0.26(14) . . . . ? N8 N9 C2 N1 -179.25(12) . . . . ? C1 N1 C2 N9 -179.62(12) . . . . ? C1 N1 C2 N6 1.0(2) . . . . ? N9 C2 N6 N7 -0.23(15) . . . . ? N1 C2 N6 N7 179.26(12) . . . . ? N5 N4 N3 N2 -0.15(16) . . . . ? C1 N2 N3 N4 0.37(16) . . . . ? N9 N8 N7 N6 0.06(14) . . . . ? C2 N6 N7 N8 0.10(14) . . . . ? N3 N4 N5 C1 -0.13(15) . . . . ? N4 N5 C1 N2 0.37(15) . . . . ? N4 N5 C1 N1 -179.80(12) . . . . ? N3 N2 C1 N5 -0.47(16) . . . . ? N3 N2 C1 N1 179.69(12) . . . . ? C2 N1 C1 N5 -2.0(2) . . . . ? C2 N1 C1 N2 177.84(13) . . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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 H3 N9 0.886(19) 2.018(19) 2.8932(17) 168.8(16) 3_755 N6 H2 N3 0.95(2) 2.01(2) 2.8510(17) 146.7(17) 2_655 N6 H2 N5 0.95(2) 2.24(2) 2.7354(16) 112.1(15) . O1 H4 N4 0.86(2) 2.05(2) 2.8082(18) 146(2) 2_645 N2 H1 O1 0.94(2) 1.69(2) 2.6231(17) 176.7(18) . O1 H5 N8 0.99(2) 1.93(2) 2.8394(18) 151.3(19) 3_755 _geom_special_details ? # Attachment 'bx069a_H2bta_DMSO.cif' data_bx069 _database_code_depnum_ccdc_archive 'CCDC 687768' _audit_creation_method SHELXL-97 _audit_creation_date ; 'Mon Feb 20 12:29:32 2006' ; _audit_update_record 13.11.2007 _chemical_name_systematic '5,5-Bis(1H-tetrazolyl)amine monoydrate dimethylsulfoxid' _chemical_compound_source ? _chemical_name_common '5,5-Bis(1H-tetrazolyl)amine monoydrate dimethylsulfoxid' _chemical_formula_moiety 'C2 H3 N9, C2 H6 O S, H2 O' _chemical_formula_sum 'C4 H11 N9 O2 S1' _chemical_formula_weight 249.54 _diffrn_ambient_temperature 200 # in K _diffrn_source_type 'Spellman generator' _diffrn_source_power ? # in kW _diffrn_source_voltage 50 # kV _diffrn_source_current 40 # mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_collimation 0.5 _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method omega-scan _diffrn_radiation_type 'Mo K\a' _diffrn_detector_area_resol_mean 15.9809 _diffrn_reflns_number 9776 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0177 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 4.30 _diffrn_reflns_theta_max 25.50 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.994 _reflns_number_total 1965 _reflns_number_gt 1846 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.0334342143 _diffrn_orient_matrix_UB_12 -0.0640009189 _diffrn_orient_matrix_UB_13 0.0169106927 _diffrn_orient_matrix_UB_21 0.0021131975 _diffrn_orient_matrix_UB_22 -0.0389197676 _diffrn_orient_matrix_UB_23 -0.0325042244 _diffrn_orient_matrix_UB_31 0.0314148216 _diffrn_orient_matrix_UB_32 0.0706996347 _diffrn_orient_matrix_UB_33 -0.0026138602 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_Int_Tables_number 15 _symmetry_space_group_name_Hall '-C 2yc' 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.9330(14) _cell_length_b 6.8863(6) _cell_length_c 19.9204(15) _cell_angle_alpha 90.00 _cell_angle_beta 104.227(7) _cell_angle_gamma 90.00 _cell_volume 2118.6(3) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3.7092 _cell_measurement_theta_max 27.4994 _cell_special_details ? _exptl_crystal_description rods _exptl_crystal_colour colorless _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.563 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.312 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.96577 _exptl_absorpt_correction_T_max 0.99000 _exptl_absorpt_process_details ;SCALE3 ABSPACK - An Oxford Diffraction program (1.0.4,gui:1.0.3) (C) 2005 Oxford Diffraction Ltd. ; _exptl_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist ? ? ? ? _diffrn_special_details ? _refine_diff_density_max 0.343 _refine_diff_density_min -0.339 _refine_diff_density_rms 0.051 _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_structure_solution SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid # Plot Program for Crystal Structure Illustrations, Oak Ridge National # Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ. # Glasgow) used --- SCHAKAL (E. Keller, University of Freiburg (Breisgau), # Germany, 1995)' ; _computing_publication_material ;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version). # --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses). ; _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 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1965 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1067 _refine_ls_wR_factor_gt 0.1035 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _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 S S 0.85882(3) 0.14360(7) 0.60626(2) 0.03078(19) Uani 1 1 d . . . O1 O 0.67860(11) -0.0999(3) 0.46601(8) 0.0369(4) Uani 1 1 d . . . O2 O 0.76920(9) 0.0602(3) 0.58967(7) 0.0410(4) Uani 1 1 d . . . N6 N 0.75132(10) 0.0626(3) 0.85875(9) 0.0308(4) Uani 1 1 d . . . N7 N 0.83787(11) 0.0722(3) 0.86748(9) 0.0384(4) Uani 1 1 d . . . N3 N 0.57352(10) 0.0354(3) 0.58311(8) 0.0332(4) Uani 1 1 d . . . N1 N 0.62926(10) 0.0317(3) 0.76351(8) 0.0312(4) Uani 1 1 d . . . N4 N 0.50017(10) 0.0189(3) 0.59785(9) 0.0348(4) Uani 1 1 d . . . N2 N 0.63355(11) 0.0420(3) 0.64383(8) 0.0283(4) Uani 1 1 d . . . N9 N 0.77612(10) 0.0457(3) 0.75715(9) 0.0338(4) Uani 1 1 d . . . N5 N 0.50958(10) 0.0138(3) 0.66753(8) 0.0308(4) Uani 1 1 d . . . N8 N 0.85168(11) 0.0623(3) 0.80673(9) 0.0392(4) Uani 1 1 d . . . C2 C 0.71579(12) 0.0465(3) 0.79164(9) 0.0262(4) Uani 1 1 d . . . C3 C 0.89588(16) 0.1047(4) 0.53048(12) 0.0441(6) Uani 1 1 d . . . H3A H 0.8648 0.1912 0.4936 0.066 Uiso 1 1 calc R . . H3B H 0.8853 -0.0306 0.5156 0.066 Uiso 1 1 calc R . . H3C H 0.9581 0.1321 0.5403 0.066 Uiso 1 1 calc R . . C1 C 0.59342(11) 0.0290(3) 0.69459(9) 0.0253(4) Uani 1 1 d . . . C4 C 0.92589(15) -0.0274(4) 0.65978(12) 0.0465(6) Uani 1 1 d . . . H4A H 0.9141 -0.0262 0.7058 0.070 Uiso 1 1 calc R . . H4B H 0.9867 0.0060 0.6638 0.070 Uiso 1 1 calc R . . H4C H 0.9141 -0.1572 0.6394 0.070 Uiso 1 1 calc R . . H1 H 0.5925(16) 0.022(3) 0.7884(13) 0.038(6) Uiso 1 1 d . . . H2 H 0.6862(17) 0.056(3) 0.6429(13) 0.042(7) Uiso 1 1 d . . . H6 H 0.7272(17) 0.075(4) 0.8940(14) 0.046(7) Uiso 1 1 d . . . H1A H 0.7086(18) -0.071(4) 0.5043(17) 0.052(8) Uiso 1 1 d . . . H1B H 0.626(2) -0.077(5) 0.4602(18) 0.076(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S 0.0245(3) 0.0396(3) 0.0301(3) -0.0041(2) 0.0103(2) -0.00073(19) O1 0.0246(8) 0.0605(10) 0.0250(8) -0.0031(7) 0.0052(6) 0.0045(7) O2 0.0203(7) 0.0756(11) 0.0284(7) -0.0098(7) 0.0085(6) -0.0054(7) N6 0.0217(8) 0.0464(10) 0.0249(8) 0.0006(7) 0.0066(7) -0.0036(7) N7 0.0227(9) 0.0586(12) 0.0323(9) 0.0021(8) 0.0038(7) -0.0046(8) N3 0.0220(8) 0.0544(11) 0.0233(8) 0.0011(7) 0.0059(6) -0.0026(7) N1 0.0180(8) 0.0545(11) 0.0233(8) -0.0012(7) 0.0093(6) -0.0015(7) N4 0.0220(8) 0.0571(11) 0.0258(8) -0.0003(8) 0.0070(6) -0.0004(7) N2 0.0188(8) 0.0440(10) 0.0237(8) -0.0005(7) 0.0082(6) -0.0024(7) N9 0.0193(8) 0.0545(11) 0.0288(9) -0.0019(8) 0.0082(7) -0.0006(7) N5 0.0193(8) 0.0482(10) 0.0253(8) -0.0013(7) 0.0063(6) -0.0005(7) N8 0.0223(9) 0.0626(12) 0.0325(9) 0.0002(8) 0.0061(7) -0.0023(8) C2 0.0219(9) 0.0352(10) 0.0225(9) -0.0001(7) 0.0076(7) 0.0001(7) C3 0.0453(13) 0.0554(14) 0.0391(12) -0.0020(10) 0.0248(10) -0.0068(11) C1 0.0194(9) 0.0339(10) 0.0240(9) -0.0002(7) 0.0080(7) 0.0000(7) C4 0.0298(12) 0.0710(17) 0.0386(12) 0.0085(11) 0.0082(9) 0.0105(11) 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 S O2 1.4988(15) . ? S C4 1.762(2) . ? S C3 1.771(2) . ? O1 H1A 0.82(3) . ? O1 H1B 0.83(4) . ? N6 C2 1.322(3) . ? N6 N7 1.348(2) . ? N6 H6 0.88(3) . ? N7 N8 1.284(2) . ? N3 N4 1.278(2) . ? N3 N2 1.346(2) . ? N1 C1 1.351(2) . ? N1 C2 1.358(2) . ? N1 H1 0.86(2) . ? N4 N5 1.360(2) . ? N2 C1 1.326(2) . ? N2 H2 0.85(3) . ? N9 C2 1.312(2) . ? N9 N8 1.361(2) . ? N5 C1 1.316(2) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 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 O2 S C4 106.29(11) . . ? O2 S C3 104.67(10) . . ? C4 S C3 97.75(12) . . ? H1A O1 H1B 115(3) . . ? C2 N6 N7 107.74(16) . . ? C2 N6 H6 130.5(17) . . ? N7 N6 H6 121.6(17) . . ? N8 N7 N6 106.41(16) . . ? N4 N3 N2 106.53(15) . . ? C1 N1 C2 123.55(16) . . ? C1 N1 H1 114.1(17) . . ? C2 N1 H1 122.3(17) . . ? N3 N4 N5 111.05(16) . . ? C1 N2 N3 108.29(15) . . ? C1 N2 H2 133.5(17) . . ? N3 N2 H2 118.2(17) . . ? C2 N9 N8 104.52(16) . . ? C1 N5 N4 105.21(15) . . ? N7 N8 N9 111.25(16) . . ? N9 C2 N6 110.08(17) . . ? N9 C2 N1 125.72(17) . . ? N6 C2 N1 124.21(16) . . ? S C3 H3A 109.5 . . ? S C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? S C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N5 C1 N2 108.92(16) . . ? N5 C1 N1 123.38(16) . . ? N2 C1 N1 127.70(17) . . ? S C4 H4A 109.5 . . ? S C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? S C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 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 C2 N6 N7 N8 0.2(2) . . . . ? N2 N3 N4 N5 -0.1(2) . . . . ? N4 N3 N2 C1 0.0(2) . . . . ? N3 N4 N5 C1 0.2(2) . . . . ? N6 N7 N8 N9 -0.2(3) . . . . ? C2 N9 N8 N7 0.1(3) . . . . ? N8 N9 C2 N6 0.0(2) . . . . ? N8 N9 C2 N1 -179.61(19) . . . . ? N7 N6 C2 N9 -0.1(2) . . . . ? N7 N6 C2 N1 179.51(19) . . . . ? C1 N1 C2 N9 -5.2(3) . . . . ? C1 N1 C2 N6 175.21(19) . . . . ? N4 N5 C1 N2 -0.2(2) . . . . ? N4 N5 C1 N1 179.25(18) . . . . ? N3 N2 C1 N5 0.2(2) . . . . ? N3 N2 C1 N1 -179.29(19) . . . . ? C2 N1 C1 N5 179.67(19) . . . . ? C2 N1 C1 N2 -1.0(3) . . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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 N5 0.86(2) 2.03(3) 2.879(2) 170(2) 2_656 N2 H2 O2 0.85(3) 1.89(3) 2.645(2) 148(2) . N2 H2 N9 0.85(3) 2.37(3) 2.781(2) 110(2) . N6 H6 O1 0.88(3) 1.80(3) 2.682(2) 180(3) 6_556 O1 H1A O2 0.82(3) 1.96(3) 2.760(2) 167(3) . O1 H1B N4 0.83(4) 2.10(4) 2.874(2) 155(3) 5_656 _geom_special_details ? # Attachment 'bx211ma_Me3bta.cif' data_bx211ma _database_code_depnum_ccdc_archive 'CCDC 687769' _audit_creation_method SHELXL-97 _audit_creation_date ; 'Thu May 18 10:34:01 2006' ; _audit_update_record 13.09.2006 _chemical_name_systematic 5,5-Bis(2-methyltetrazolyl)methylamine _chemical_compound_source ? _chemical_name_common 5,5-Bis(2-methyltetrazolyl)methylamine _chemical_formula_moiety 'C5 H9 N9' _chemical_formula_sum 'C5 H9 N9' _chemical_formula_weight 195.21 _diffrn_ambient_temperature 200 # in K _diffrn_source_type 'Spellman generator' _diffrn_source_power ? # in kW _diffrn_source_voltage 50 # kV _diffrn_source_current 40 # mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_collimation 0.5 _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method omega-scan _diffrn_radiation_type 'Mo K\a' _diffrn_detector_area_resol_mean 15.9809 _diffrn_reflns_number 2226 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0377 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 4.12 _diffrn_reflns_theta_max 26.00 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _reflns_number_total 862 _reflns_number_gt 724 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.0771653970 _diffrn_orient_matrix_UB_12 -0.0289365917 _diffrn_orient_matrix_UB_13 0.0597697157 _diffrn_orient_matrix_UB_21 -0.1426464555 _diffrn_orient_matrix_UB_22 -0.0208371567 _diffrn_orient_matrix_UB_23 -0.0447754639 _diffrn_orient_matrix_UB_31 0.0890912670 _diffrn_orient_matrix_UB_32 -0.0081204923 _diffrn_orient_matrix_UB_33 -0.0984096142 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/m _symmetry_Int_Tables_number ? _symmetry_space_group_name_Hall '-P 2yb' 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 3.8520(12) _cell_length_b 19.395(5) _cell_length_c 5.7690(18) _cell_angle_alpha 90.00 _cell_angle_beta 95.60(3) _cell_angle_gamma 90.00 _cell_volume 428.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 4.1154 _cell_measurement_theta_max 27.4931 _cell_special_details ? _exptl_crystal_description needles _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.96111 _exptl_absorpt_correction_T_max 0.99000 _exptl_absorpt_process_details ;SCALE3 ABSPACK - An Oxford Diffraction program (1.0.4,gui:1.0.3) (C) 2005 Oxford Diffraction Ltd. ; _exptl_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist ? ? ? ? _diffrn_special_details ? _refine_diff_density_max 0.215 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.050 _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_structure_solution SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid # Plot Program for Crystal Structure Illustrations, Oak Ridge National # Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ. # Glasgow) used --- SCHAKAL (E. Keller, University of Freiburg (Breisgau), # Germany, 1995)' ; _computing_publication_material ;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version). # --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses). ; _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 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 862 _refine_ls_number_parameters 86 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0714 _refine_ls_R_factor_gt 0.0570 _refine_ls_wR_factor_ref 0.1353 _refine_ls_wR_factor_gt 0.1252 _refine_ls_goodness_of_fit_ref 1.176 _refine_ls_restrained_S_all 1.176 _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 C5 C 0.7921(10) 0.7500 1.4554(6) 0.0381(8) Uani 1 2 d S . . C3 C 0.0926(8) 0.57015(14) 0.7316(5) 0.0395(7) Uani 1 1 d . . . H1 H 0.943(8) 0.7088(14) 1.470(5) 0.056(8) Uiso 1 1 d . . . H6 H -0.090(9) 0.5930(16) 0.665(5) 0.065(9) Uiso 1 1 d . . . H4 H 0.258(8) 0.5695(16) 0.606(5) 0.065(9) Uiso 1 1 d . . . H5 H 0.066(8) 0.5246(18) 0.782(6) 0.075(10) Uiso 1 1 d . . . H2 H 0.641(12) 0.7500 1.583(7) 0.064(13) Uiso 1 2 d S . . N3 N 0.2646(5) 0.60868(9) 0.9264(3) 0.0323(5) Uani 1 1 d . . . N1 N 0.5964(7) 0.7500 1.2239(4) 0.0327(7) Uani 1 2 d S . . N2 N 0.3074(5) 0.67733(9) 0.9236(3) 0.0330(5) Uani 1 1 d . . . N4 N 0.3996(6) 0.57888(10) 1.1176(3) 0.0414(6) Uani 1 1 d . . . N5 N 0.5412(6) 0.62860(10) 1.2541(3) 0.0402(6) Uani 1 1 d . . . C1 C 0.4802(5) 0.68755(11) 1.1310(4) 0.0287(5) 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 C5 0.040(2) 0.042(2) 0.0298(19) 0.000 -0.0057(15) 0.000 C3 0.0464(15) 0.0335(14) 0.0363(15) -0.0013(11) -0.0070(12) -0.0050(12) N3 0.0403(11) 0.0281(10) 0.0279(10) 0.0016(8) 0.0007(8) 0.0008(8) N1 0.0396(15) 0.0299(14) 0.0275(14) 0.000 -0.0029(12) 0.000 N2 0.0397(11) 0.0280(10) 0.0303(11) 0.0014(8) -0.0018(8) -0.0026(8) N4 0.0606(14) 0.0300(11) 0.0319(11) 0.0023(8) -0.0034(10) 0.0020(9) N5 0.0530(13) 0.0324(11) 0.0334(11) 0.0012(8) -0.0053(9) 0.0034(9) C1 0.0313(11) 0.0290(12) 0.0261(12) 0.0019(9) 0.0037(9) 0.0030(9) 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 C5 N1 1.468(4) . ? C5 H1 0.99(3) . ? C5 H2 0.98(4) . ? C3 N3 1.454(3) . ? C3 H6 0.88(3) . ? C3 H4 1.01(3) . ? C3 H5 0.94(4) . ? N3 N4 1.307(3) . ? N3 N2 1.342(3) . ? N1 C1 1.381(2) . ? N1 C1 1.381(2) 4_575 ? N2 C1 1.326(3) . ? N4 N5 1.328(3) . ? N5 C1 1.354(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 N1 C5 H1 108.9(16) . . ? N1 C5 H2 113(3) . . ? H1 C5 H2 109(2) . . ? N3 C3 H6 111(2) . . ? N3 C3 H4 106.8(18) . . ? H6 C3 H4 103(3) . . ? N3 C3 H5 107(2) . . ? H6 C3 H5 120(3) . . ? H4 C3 H5 108(3) . . ? N4 N3 N2 114.17(17) . . ? N4 N3 C3 122.6(2) . . ? N2 N3 C3 123.22(18) . . ? C1 N1 C1 122.5(3) . 4_575 ? C1 N1 C5 118.12(13) . . ? C1 N1 C5 118.12(13) 4_575 . ? C1 N2 N3 100.90(16) . . ? N3 N4 N5 106.61(18) . . ? N4 N5 C1 105.19(18) . . ? N2 C1 N5 113.13(19) . . ? N2 C1 N1 126.6(2) . . ? N5 C1 N1 120.2(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 N4 N3 N2 C1 -0.2(2) . . . . ? C3 N3 N2 C1 -178.5(2) . . . . ? N2 N3 N4 N5 0.2(3) . . . . ? C3 N3 N4 N5 178.5(2) . . . . ? N3 N4 N5 C1 -0.1(2) . . . . ? N3 N2 C1 N5 0.2(2) . . . . ? N3 N2 C1 N1 179.9(2) . . . . ? N4 N5 C1 N2 0.0(3) . . . . ? N4 N5 C1 N1 -179.8(2) . . . . ? C1 N1 C1 N2 14.6(4) 4_575 . . . ? C5 N1 C1 N2 -178.4(3) . . . . ? C1 N1 C1 N5 -165.77(18) 4_575 . . . ? C5 N1 C1 N5 1.3(4) . . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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 ? ? ? ? ? ? ? ? _geom_special_details ? # Attachment 'jn436_Me2bta.cif' data_jn536 _database_code_depnum_ccdc_archive 'CCDC 687770' _audit_creation_method SHELXL-97 _audit_creation_date 19-Oct-05 _audit_update_record ? _chemical_name_systematic Bis-(2-methyl-tetrazolyl)amine _chemical_compound_source ? _chemical_name_common Bis-(2-methyl-tetrazolyl)amine _chemical_formula_moiety 'C4 H7 N9' _chemical_formula_sum 'C4 H7 N9' _chemical_formula_weight 181.19 _diffrn_ambient_temperature 200 # in K _diffrn_source_type 'Spellman generator' _diffrn_source_power 2.250 # in kW _diffrn_source_voltage 50 # kV _diffrn_source_current 45 # mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_collimation 0.5 _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method omega-scan _diffrn_radiation_type 'Mo K\a' _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 3457 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 27.49 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _reflns_number_total 1803 _reflns_number_gt 1383 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.1336822 _diffrn_orient_matrix_UB_12 -0.0217507 _diffrn_orient_matrix_UB_13 0.0417069 _diffrn_orient_matrix_UB_21 0.0608309 _diffrn_orient_matrix_UB_22 0.0211081 _diffrn_orient_matrix_UB_23 -0.0822828 _diffrn_orient_matrix_UB_31 0.0196029 _diffrn_orient_matrix_UB_32 0.0828276 _diffrn_orient_matrix_UB_33 0.0319216 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2ybc' 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' 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 10.279(2) _cell_length_b 11.338(2) _cell_length_c 6.7720(14) _cell_angle_alpha 90.00 _cell_angle_beta 94.74(3) _cell_angle_gamma 90.00 _cell_volume 786.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 1885 _cell_measurement_theta_min 3.134 _cell_measurement_theta_max 27.485 _cell_special_details ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.530 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 0 0.100000 0 -1 0 0.120000 1 0 0 0.050000 -1 0 0 0.050000 0 0 1 0.040000 0 0 -1 0.040000 8 -9 -17 0.080000 -8 9 17 0.080000 1 -1 3 0.070000 -1 1 -3 0.060000 loop_ _diffrn_radiation_wavelength_id 0.71073 _diffrn_special_details ? _refine_diff_density_max 0.192 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.051 _computing_structure_solution SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid # Plot Program for Crystal Structure Illustrations, Oak Ridge National # Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ. # Glasgow) used --- SCHAKAL (E. Keller, University of Freiburg (Breisgau), # Germany, 1995)' ; _computing_publication_material ;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version). # --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses). ; _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 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1803 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0573 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1171 _refine_ls_wR_factor_gt 0.1096 _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_restrained_S_all 1.139 _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 N8 N 2.05416(13) 0.82899(13) 0.7507(2) 0.0323(4) Uani 1 1 d . . . N6 N 2.22311(12) 0.71277(12) 0.8450(2) 0.0273(3) Uani 1 1 d . . . N7 N 2.09665(13) 0.72062(12) 0.7781(2) 0.0276(3) Uani 1 1 d . . . N9 N 2.15509(12) 0.89916(12) 0.7989(2) 0.0315(4) Uani 1 1 d . . . N3 N 2.62506(12) 0.68561(12) 1.05099(19) 0.0278(3) Uani 1 1 d . . . N2 N 2.49909(12) 0.69469(12) 0.9803(2) 0.0272(3) Uani 1 1 d . . . C1 C 2.48470(14) 0.81120(14) 0.9777(2) 0.0238(3) Uani 1 1 d . . . N5 N 2.59501(13) 0.86958(12) 1.0425(2) 0.0298(3) Uani 1 1 d . . . C2 C 2.25481(14) 0.82613(14) 0.8560(2) 0.0241(3) Uani 1 1 d . . . N4 N 2.68380(13) 0.78653(13) 1.0870(2) 0.0313(4) Uani 1 1 d . . . N1 N 2.37413(12) 0.87291(13) 0.9185(2) 0.0283(3) Uani 1 1 d . . . C4 C 2.01231(18) 0.61845(17) 0.7478(3) 0.0348(4) Uani 1 1 d . . . C3 C 2.69172(19) 0.57250(18) 1.0754(3) 0.0387(5) Uani 1 1 d . . . H4 H 1.930(2) 0.647(2) 0.686(3) 0.055(6) Uiso 1 1 d . . . H7 H 2.3771(17) 0.953(2) 0.929(2) 0.035(5) Uiso 1 1 d . . . H1 H 2.633(2) 0.518(2) 1.118(3) 0.068(8) Uiso 1 1 d . . . H6 H 2.052(2) 0.561(2) 0.664(3) 0.055(6) Uiso 1 1 d . . . H5 H 2.002(2) 0.580(2) 0.866(3) 0.053(6) Uiso 1 1 d . . . H2 H 2.770(3) 0.588(3) 1.159(4) 0.081(8) Uiso 1 1 d . . . H3 H 2.715(2) 0.544(3) 0.954(4) 0.084(9) 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 N8 0.0251(7) 0.0265(8) 0.0443(8) 0.0015(6) -0.0031(6) 0.0002(6) N6 0.0219(7) 0.0236(7) 0.0353(7) 0.0006(5) -0.0030(5) -0.0020(5) N7 0.0233(7) 0.0251(8) 0.0336(7) 0.0015(5) -0.0029(5) -0.0013(5) N9 0.0256(7) 0.0234(7) 0.0447(8) 0.0014(6) -0.0020(6) -0.0001(6) N3 0.0251(7) 0.0249(8) 0.0327(7) -0.0019(5) -0.0015(5) 0.0021(5) N2 0.0237(6) 0.0237(7) 0.0336(7) -0.0010(5) -0.0008(5) 0.0006(5) C1 0.0242(8) 0.0223(8) 0.0250(8) -0.0003(6) 0.0020(6) -0.0008(6) N5 0.0237(7) 0.0259(8) 0.0387(8) 0.0001(6) -0.0039(5) -0.0016(6) C2 0.0223(8) 0.0221(8) 0.0278(8) 0.0003(6) 0.0008(6) 0.0001(6) N4 0.0262(7) 0.0268(8) 0.0398(8) -0.0013(6) -0.0035(6) -0.0005(6) N1 0.0238(7) 0.0196(7) 0.0406(8) -0.0007(5) -0.0034(5) -0.0014(5) C4 0.0296(9) 0.0300(10) 0.0436(11) 0.0004(8) -0.0042(7) -0.0088(8) C3 0.0352(10) 0.0295(10) 0.0503(12) -0.0022(8) -0.0040(8) 0.0095(8) 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 N8 N7 1.312(2) . ? N8 N9 1.3266(19) . ? N6 C2 1.327(2) . ? N6 N7 1.3436(18) . ? N7 C4 1.451(2) . ? N9 C2 1.349(2) . ? N3 N4 1.307(2) . ? N3 N2 1.3468(18) . ? N3 C3 1.457(2) . ? N2 C1 1.329(2) . ? C1 N5 1.354(2) . ? C1 N1 1.366(2) . ? N5 N4 1.329(2) . ? C2 N1 1.371(2) . ? N1 H7 0.92(2) . ? C4 H4 0.97(2) . ? C4 H6 0.98(2) . ? C4 H5 0.93(2) . ? C3 H1 0.93(3) . ? C3 H2 0.96(3) . ? C3 H3 0.94(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 N7 N8 N9 106.41(13) . . ? C2 N6 N7 100.43(13) . . ? N8 N7 N6 114.28(13) . . ? N8 N7 C4 122.65(14) . . ? N6 N7 C4 123.01(14) . . ? N8 N9 C2 105.22(14) . . ? N4 N3 N2 114.53(13) . . ? N4 N3 C3 122.92(14) . . ? N2 N3 C3 122.48(14) . . ? C1 N2 N3 100.57(12) . . ? N2 C1 N5 113.09(13) . . ? N2 C1 N1 127.00(14) . . ? N5 C1 N1 119.91(14) . . ? N4 N5 C1 105.56(13) . . ? N6 C2 N9 113.66(13) . . ? N6 C2 N1 126.99(14) . . ? N9 C2 N1 119.36(14) . . ? N3 N4 N5 106.25(13) . . ? C1 N1 C2 126.43(14) . . ? C1 N1 H7 117.8(11) . . ? C2 N1 H7 115.7(11) . . ? N7 C4 H4 106.9(14) . . ? N7 C4 H6 110.3(13) . . ? H4 C4 H6 111.1(17) . . ? N7 C4 H5 111.3(14) . . ? H4 C4 H5 111.5(17) . . ? H6 C4 H5 106(2) . . ? N3 C3 H1 107.7(15) . . ? N3 C3 H2 105.9(18) . . ? H1 C3 H2 118(2) . . ? N3 C3 H3 111.0(17) . . ? H1 C3 H3 106(2) . . ? H2 C3 H3 108(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 N9 N8 N7 N6 0.49(17) . . . . ? N9 N8 N7 C4 177.66(14) . . . . ? C2 N6 N7 N8 -0.11(17) . . . . ? C2 N6 N7 C4 -177.28(15) . . . . ? N7 N8 N9 C2 -0.62(16) . . . . ? N4 N3 N2 C1 -0.60(17) . . . . ? C3 N3 N2 C1 -177.62(15) . . . . ? N3 N2 C1 N5 0.08(16) . . . . ? N3 N2 C1 N1 -179.89(15) . . . . ? N2 C1 N5 N4 0.43(18) . . . . ? N1 C1 N5 N4 -179.60(14) . . . . ? N7 N6 C2 N9 -0.31(17) . . . . ? N7 N6 C2 N1 179.24(15) . . . . ? N8 N9 C2 N6 0.61(17) . . . . ? N8 N9 C2 N1 -178.98(14) . . . . ? N2 N3 N4 N5 0.89(18) . . . . ? C3 N3 N4 N5 177.90(15) . . . . ? C1 N5 N4 N3 -0.76(17) . . . . ? N2 C1 N1 C2 2.2(3) . . . . ? N5 C1 N1 C2 -177.73(14) . . . . ? N6 C2 N1 C1 1.6(3) . . . . ? N9 C2 N1 C1 -178.88(14) . . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? _geom_special_details ? # Attachment 'ln186_H2bta.cif' data_ln186 _database_code_depnum_ccdc_archive 'CCDC 687771' _audit_creation_method SHELXL-97 _audit_creation_date 13-Apr-07 _audit_update_record ? _chemical_name_systematic N,N-Bis(1H-tetrazol-5-yl)amine _chemical_compound_source ? _chemical_name_common N,N-Bis(1H-tetrazol-5-yl)amine _chemical_formula_moiety 'C2 H3 N9' _chemical_formula_sum 'C2 H3 N9' _chemical_formula_weight 153.13 _diffrn_ambient_temperature 200 # in K _diffrn_source_type 'Spellman generator' _diffrn_source_power 3.025 # in kW _diffrn_source_voltage 55.00 _diffrn_source_current 55.00 _kl_diffrn_measurement_scan_step_degree 1.50 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'vertically mounted graphite crystal' _diffrn_radiation_collimation 0.5 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method omega-scan _diffrn_radiation_type 'Mo K\a' _diffrn_detector_area_resol_mean 9 _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _diffrn_reflns_number 4201 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 26.49 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.49 _diffrn_measured_fraction_theta_full 0.998 _reflns_number_total 2257 _reflns_number_gt 1618 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_UB_11 0.0729009 _diffrn_orient_matrix_UB_12 -0.0643447 _diffrn_orient_matrix_UB_13 -0.0089618 _diffrn_orient_matrix_UB_21 0.0731543 _diffrn_orient_matrix_UB_22 0.0438376 _diffrn_orient_matrix_UB_23 0.0259880 _diffrn_orient_matrix_UB_31 -0.0328495 _diffrn_orient_matrix_UB_32 -0.0451721 _diffrn_orient_matrix_UB_33 0.0379858 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_Int_Tables_number 61 _symmetry_space_group_name_Hall '-P 2ac 2ab' 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.109(2) _cell_length_b 9.2272(18) _cell_length_c 21.327(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2186.2(7) _cell_formula_units_Z 16 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 17997 _cell_measurement_theta_min 3.134 _cell_measurement_theta_max 27.485 _cell_special_details ? _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.861 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.147 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.020000 0 0 -1 0.030000 0 1 0 0.020000 0 -1 0 0.040000 1 0 0 0.080000 -1 0 0 0.110000 _diffrn_special_details ? _refine_diff_density_max 0.252 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.060 _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid # Plot Program for Crystal Structure Illustrations, Oak Ridge National # Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ. # Glasgow) used --- SCHAKAL (E. Keller, University of Freiburg (Breisgau), # Germany, 1995)' ; _computing_publication_material ;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version). # --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses). ; _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 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2257 _refine_ls_number_parameters 223 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1022 _refine_ls_wR_factor_gt 0.0910 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 H12 H 0.9323(17) 0.313(2) 0.3496(8) 0.026(5) Uiso 1 1 d . . . H1 H 0.7578(17) 0.319(3) 0.1883(8) 0.033(6) Uiso 1 1 d . . . H16 H 1.2027(16) 0.297(2) 0.5443(9) 0.027(5) Uiso 1 1 d . . . H6 H 0.6262(17) 0.311(2) 0.2863(9) 0.034(6) Uiso 1 1 d . . . H11 H 1.064(2) 0.312(3) 0.4493(11) 0.062(7) Uiso 1 1 d . . . H2 H 0.896(2) 0.325(3) 0.0939(10) 0.050(7) Uiso 1 1 d . . . N6 N 0.63976(13) 0.21983(17) 0.27951(7) 0.0241(4) Uani 1 1 d . . . C1 C 0.82066(14) 0.15387(18) 0.14078(8) 0.0187(4) Uani 1 1 d . . . N2 N 0.88117(13) 0.22649(16) 0.09653(7) 0.0231(4) Uani 1 1 d . . . N1 N 0.75473(13) 0.22195(17) 0.18607(7) 0.0221(3) Uani 1 1 d . . . C2 C 0.69819(14) 0.14991(18) 0.23367(8) 0.0196(4) Uani 1 1 d . . . N9 N 0.68972(12) 0.00893(15) 0.24293(7) 0.0215(3) Uani 1 1 d . . . N3 N 0.93687(13) 0.12911(16) 0.05922(7) 0.0258(4) Uani 1 1 d . . . N5 N 0.83412(13) 0.01358(15) 0.13189(7) 0.0222(4) Uani 1 1 d . . . N8 N 0.62422(13) -0.00481(16) 0.29709(7) 0.0255(4) Uani 1 1 d . . . N4 N 0.90769(13) 0.00358(15) 0.08066(7) 0.0242(4) Uani 1 1 d . . . N7 N 0.59437(14) 0.11976(16) 0.31929(7) 0.0277(4) Uani 1 1 d . . . N12 N 0.95004(13) 0.21830(16) 0.35359(7) 0.0237(4) Uani 1 1 d . . . C11 C 1.01228(14) 0.14322(17) 0.39662(8) 0.0193(4) Uani 1 1 d . . . N14 N 0.94343(13) -0.00238(15) 0.32788(7) 0.0238(4) Uani 1 1 d . . . C12 C 1.13358(15) 0.13377(18) 0.48968(8) 0.0193(4) Uani 1 1 d . . . N15 N 1.01069(13) 0.00450(14) 0.38156(7) 0.0209(3) Uani 1 1 d . . . N19 N 1.15658(13) -0.00605(16) 0.49247(7) 0.0226(4) Uani 1 1 d . . . N16 N 1.19070(13) 0.20155(16) 0.53660(7) 0.0224(4) Uani 1 1 d . . . N11 N 1.06685(13) 0.20754(16) 0.44644(7) 0.0220(4) Uani 1 1 d . . . N18 N 1.23165(13) -0.02004(16) 0.54296(7) 0.0247(4) Uani 1 1 d . . . N13 N 0.90719(13) 0.12382(16) 0.31060(7) 0.0260(4) Uani 1 1 d . . . N17 N 1.25358(14) 0.10285(16) 0.56942(7) 0.0252(4) 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 N6 0.0299(8) 0.0145(8) 0.0278(8) 0.0000(7) 0.0030(7) 0.0014(7) C1 0.0198(8) 0.0169(9) 0.0194(9) 0.0008(7) -0.0041(7) -0.0009(7) N2 0.0287(8) 0.0133(8) 0.0274(8) 0.0001(7) 0.0033(7) -0.0002(6) N1 0.0295(8) 0.0110(8) 0.0259(8) 0.0008(6) 0.0039(7) 0.0000(6) C2 0.0193(8) 0.0167(9) 0.0229(9) -0.0010(7) -0.0028(7) -0.0006(7) N9 0.0248(7) 0.0173(8) 0.0222(8) 0.0010(6) -0.0008(6) -0.0008(6) N3 0.0320(8) 0.0193(8) 0.0263(9) -0.0012(7) 0.0028(7) -0.0001(6) N5 0.0276(8) 0.0151(8) 0.0237(8) -0.0011(6) 0.0018(6) -0.0002(6) N8 0.0307(8) 0.0212(8) 0.0246(8) 0.0018(6) 0.0027(7) 0.0003(7) N4 0.0298(8) 0.0173(8) 0.0255(8) -0.0010(6) 0.0017(7) -0.0016(7) N7 0.0340(9) 0.0207(8) 0.0283(9) 0.0015(7) 0.0056(7) 0.0002(7) N12 0.0275(8) 0.0148(8) 0.0289(9) -0.0013(6) -0.0041(7) 0.0017(6) C11 0.0182(8) 0.0185(9) 0.0211(9) 0.0017(7) 0.0032(7) -0.0010(7) N14 0.0237(8) 0.0237(9) 0.0241(8) -0.0027(7) -0.0020(6) 0.0011(7) C12 0.0217(8) 0.0164(9) 0.0198(9) 0.0003(7) 0.0033(7) -0.0015(7) N15 0.0246(7) 0.0167(8) 0.0214(8) -0.0001(6) -0.0009(6) 0.0002(6) N19 0.0272(8) 0.0179(8) 0.0226(8) 0.0009(6) 0.0006(6) 0.0022(6) N16 0.0291(8) 0.0146(8) 0.0236(8) -0.0005(7) -0.0023(7) -0.0006(6) N11 0.0305(8) 0.0146(8) 0.0209(8) -0.0015(6) -0.0021(7) 0.0008(6) N18 0.0298(8) 0.0202(8) 0.0241(8) -0.0001(6) -0.0022(7) 0.0009(6) N13 0.0282(8) 0.0203(8) 0.0294(9) -0.0019(7) -0.0058(7) 0.0000(7) N17 0.0298(8) 0.0191(8) 0.0268(8) 0.0005(6) -0.0006(7) 0.0004(6) 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 N6 C2 1.339(2) . ? N6 N7 1.352(2) . ? N6 H6 0.86(2) . ? C1 N5 1.317(2) . ? C1 N2 1.339(2) . ? C1 N1 1.365(2) . ? N2 N3 1.350(2) . ? N2 H2 0.92(2) . ? N1 C2 1.366(2) . ? N1 H1 0.90(2) . ? C2 N9 1.319(2) . ? N9 N8 1.371(2) . ? N3 N4 1.287(2) . ? N5 N4 1.368(2) . ? N8 N7 1.287(2) . ? N12 C11 1.342(2) . ? N12 N13 1.352(2) . ? N12 H12 0.90(2) . ? C11 N15 1.320(2) . ? C11 N11 1.360(2) . ? N14 N13 1.286(2) . ? N14 N15 1.368(2) . ? C12 N19 1.317(2) . ? C12 N16 1.340(2) . ? C12 N11 1.365(2) . ? N19 N18 1.368(2) . ? N16 N17 1.344(2) . ? N16 H16 0.91(2) . ? N11 H11 0.97(3) . ? N18 N17 1.290(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 C2 N6 N7 108.05(14) . . ? C2 N6 H6 132.4(13) . . ? N7 N6 H6 119.5(13) . . ? N5 C1 N2 109.49(15) . . ? N5 C1 N1 127.96(16) . . ? N2 C1 N1 122.54(16) . . ? C1 N2 N3 108.21(14) . . ? C1 N2 H2 128.5(14) . . ? N3 N2 H2 122.5(14) . . ? C1 N1 C2 123.26(16) . . ? C1 N1 H1 118.4(12) . . ? C2 N1 H1 117.7(12) . . ? N9 C2 N6 109.34(15) . . ? N9 C2 N1 128.59(16) . . ? N6 C2 N1 122.06(16) . . ? C2 N9 N8 104.79(14) . . ? N4 N3 N2 105.92(14) . . ? C1 N5 N4 104.43(14) . . ? N7 N8 N9 111.36(14) . . ? N3 N4 N5 111.94(13) . . ? N8 N7 N6 106.45(14) . . ? C11 N12 N13 108.20(14) . . ? C11 N12 H12 132.7(12) . . ? N13 N12 H12 119.0(12) . . ? N15 C11 N12 109.12(15) . . ? N15 C11 N11 128.27(15) . . ? N12 C11 N11 122.61(15) . . ? N13 N14 N15 111.64(13) . . ? N19 C12 N16 109.38(15) . . ? N19 C12 N11 128.64(16) . . ? N16 C12 N11 121.94(16) . . ? C11 N15 N14 104.82(13) . . ? C12 N19 N18 104.26(14) . . ? C12 N16 N17 108.59(14) . . ? C12 N16 H16 131.2(12) . . ? N17 N16 H16 119.2(12) . . ? C11 N11 C12 123.54(15) . . ? C11 N11 H11 118.1(14) . . ? C12 N11 H11 118.1(14) . . ? N17 N18 N19 112.12(14) . . ? N14 N13 N12 106.21(14) . . ? N18 N17 N16 105.64(14) . . ? 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 N2 N3 -1.35(19) . . . . ? N1 C1 N2 N3 179.91(15) . . . . ? N5 C1 N1 C2 5.4(3) . . . . ? N2 C1 N1 C2 -176.09(15) . . . . ? N7 N6 C2 N9 0.77(19) . . . . ? N7 N6 C2 N1 -179.69(15) . . . . ? C1 N1 C2 N9 -4.4(3) . . . . ? C1 N1 C2 N6 176.14(15) . . . . ? N6 C2 N9 N8 -0.59(18) . . . . ? N1 C2 N9 N8 179.92(16) . . . . ? C1 N2 N3 N4 1.05(18) . . . . ? N2 C1 N5 N4 1.06(18) . . . . ? N1 C1 N5 N4 179.72(16) . . . . ? C2 N9 N8 N7 0.20(19) . . . . ? N2 N3 N4 N5 -0.40(19) . . . . ? C1 N5 N4 N3 -0.40(19) . . . . ? N9 N8 N7 N6 0.27(19) . . . . ? C2 N6 N7 N8 -0.63(19) . . . . ? N13 N12 C11 N15 0.58(19) . . . . ? N13 N12 C11 N11 -179.89(15) . . . . ? N12 C11 N15 N14 -0.77(18) . . . . ? N11 C11 N15 N14 179.73(16) . . . . ? N13 N14 N15 C11 0.73(19) . . . . ? N16 C12 N19 N18 -0.67(18) . . . . ? N11 C12 N19 N18 177.20(16) . . . . ? N19 C12 N16 N17 1.20(19) . . . . ? N11 C12 N16 N17 -176.84(15) . . . . ? N15 C11 N11 C12 1.5(3) . . . . ? N12 C11 N11 C12 -177.96(16) . . . . ? N19 C12 N11 C11 -0.8(3) . . . . ? N16 C12 N11 C11 176.86(15) . . . . ? C12 N19 N18 N17 -0.10(19) . . . . ? N15 N14 N13 N12 -0.38(19) . . . . ? C11 N12 N13 N14 -0.12(19) . . . . ? N19 N18 N17 N16 0.82(18) . . . . ? C12 N16 N17 N18 -1.22(18) . . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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 N9 0.90(2) 2.18(2) 2.977(2) 147.0(16) 8_765 N1 H1 N5 0.90(2) 2.39(2) 3.090(2) 135.0(15) 8_765 N16 H16 N18 0.91(2) 1.84(2) 2.713(2) 161.5(17) 8_865 N11 H11 N4 0.97(3) 1.90(3) 2.806(2) 154(2) 3_755 N2 H2 N15 0.92(2) 2.02(2) 2.871(2) 152(2) 3_755 N2 H2 N19 0.92(2) 2.48(2) 3.141(2) 128.3(17) 3_755 _geom_special_details ?