data_weig4 _audit_creation_date 17-Jan-05 _audit_creation_method SHELXL-97 _audit_update_record ; ? ; _publ_contact_author_name 'Thomas M. Klap\"otke ' _publ_contact_author_address ; Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; loop_ _publ_author_name _publ_author_address 'G\'alvez-Ruiz, Juan Carlos' ;Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; 'Karaghiosoff, Konstantin' ;Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; 'Klap\"otke, Thomas M.' ;Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; 'L\"ohnwitz, Karolin' ;Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; 'Mayer, Peter' ;Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; 'N\"oth, Heinrich' ;Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; 'Polborn, Kurt' ;Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; 'Rohbogner, Christoph J.' ;Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; 'Suter, Max' ;Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; 'Weigand, Jan J.' ;Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; 'Holl, Gerhard ' ;WIWEB Swisttal-Heimerzheim Gro\sses Cent D-81377 Swisttal Bundesrepublik Deutschland ; _publ_contact_author_email tmk@cup.uni-muenchen.de _publ_contact_author_phone +49-89-2180-77491 _publ_contact_author_fax +49-89-2180-77492 _publ_requested_journal 'Inorg.Chem.' _publ_section_title ; Derivatives of 1,5-Diamino-1H-tetrazole A New Family of Energetic Heterocyclic-based Salts ; _publ_section_abstract ? _publ_section_comment ? _publ_section_references ; SHELXS-90, G. M. Sheldrick, University of G\"ottigen, Germany, (1990). SHELXL-97, G. M. Sheldrick, University of G\"ottigen, Germany, (1997). International Tables for X-Ray Crystallography, Vol. IV, The Kynoch Press, Birmingham, England, (1974). ; _chemical_name_systematic '1,5-Diamino-1H-tetrazolium perchlorate' _chemical_name_common ? _chemical_melting_point 370 _chemical_formula_moiety '(C H5 N6 1+),(Cl O4 1-)' _chemical_formula_sum 'C H5 Cl N6 O4' _chemical_formula_weight 200.56 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_int_tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.063(3) _cell_length_b 5.0125(16) _cell_length_c 15.659(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.022(5) _cell_angle_gamma 90.00 _cell_volume 700.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 20.00 _cell_measurement_theta_max 1.00 _cell_special_details ? _exptl_crystal_description rhomb _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.902 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.537 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8555 _exptl_absorpt_correction_T_max 0.9002 _exptl_absorpt_process_details ? _exptl_special_details ; Diffractometer operator M. Suter scanspeed_seconds/frame 5 1200 frames measured in phi (0-360) with chi=0 and om=2th=25 65 frames measured in om (15-35) with chi=280, 2th=29 and phi=0 Crystal mounted in perfluorpolyetheroil ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART Area-detector' _diffrn_measurement_method Hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 3744 _diffrn_reflns_av_R_equivalents 0.0731 _diffrn_reflns_av_sigmaI/netI 0.0577 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 28.62 _diffrn_measured_fraction_theta_max 0.806 _diffrn_reflns_theta_full 28.62 _diffrn_measured_fraction_theta_full 0.806 _computing_data_collection 'SMART (V4.C50)' _computing_cell_refinement 'SMART (V4.C50)' _computing_data_reduction 'SAINT (V4.D50)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (SHELXTL-Ver.5)' _computing_publication_material 'SHELXL (Sheldrick 1997)' _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. ; _reflns_number_total 1447 _reflns_number_gt 1225 _reflns_threshold_expression >2sigma(I) _reflns_special_details ? _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^)+(0.0598P)^2^+0.1511P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1447 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0466 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1061 _refine_ls_wR_factor_gt 0.1010 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.2733(2) 0.1814(3) 0.13458(10) 0.0280(4) Uani 1 1 d . . . N6 N 0.1533(2) 0.0788(4) 0.07685(12) 0.0331(4) Uani 1 1 d . . . C1 C 0.4124(2) 0.0817(4) 0.14449(12) 0.0281(4) Uani 1 1 d . . . N4 N 0.4885(2) 0.2271(4) 0.20871(11) 0.0325(4) Uani 1 1 d . . . N5 N 0.4596(3) -0.1104(5) 0.09994(13) 0.0388(5) Uani 1 1 d . . . N3 N 0.3970(2) 0.4083(4) 0.23776(11) 0.0357(4) Uani 1 1 d . . . N2 N 0.2666(2) 0.3825(4) 0.19288(11) 0.0336(4) Uani 1 1 d . . . Cl1 Cl 0.28822(5) 0.04625(10) 0.60377(3) 0.02918(19) Uani 1 1 d . . . O4 O 0.42936(19) -0.0532(4) 0.58865(10) 0.0417(4) Uani 1 1 d . . . O2 O 0.1746(2) -0.0067(4) 0.52932(10) 0.0435(5) Uani 1 1 d . . . O1 O 0.24564(17) -0.0948(3) 0.67722(9) 0.0340(4) Uani 1 1 d . . . O3 O 0.2966(2) 0.3238(3) 0.62176(12) 0.0502(5) Uani 1 1 d . . . H6A H 0.117(3) 0.203(6) 0.046(2) 0.046(8) Uiso 1 1 d . . . H5A H 0.398(4) -0.193(7) 0.062(2) 0.056(9) Uiso 1 1 d . . . H5B H 0.553(3) -0.168(5) 0.1121(17) 0.044(8) Uiso 1 1 d . . . H6B H 0.080(4) 0.047(6) 0.107(2) 0.055(9) Uiso 1 1 d . . . H4 H 0.571(3) 0.203(5) 0.2322(17) 0.039(7) 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 0.0297(9) 0.0337(10) 0.0216(7) -0.0011(6) 0.0073(6) 0.0026(7) N6 0.0290(11) 0.0440(12) 0.0256(8) 0.0013(8) 0.0025(7) -0.0008(8) C1 0.0298(11) 0.0328(11) 0.0235(8) 0.0049(7) 0.0098(7) 0.0014(8) N4 0.0254(10) 0.0441(11) 0.0288(8) 0.0019(7) 0.0068(7) -0.0002(8) N5 0.0349(12) 0.0436(12) 0.0399(10) -0.0057(8) 0.0124(9) 0.0064(9) N3 0.0363(10) 0.0417(10) 0.0304(8) -0.0040(7) 0.0093(7) -0.0018(8) N2 0.0347(11) 0.0373(10) 0.0305(8) -0.0036(7) 0.0106(7) 0.0026(8) Cl1 0.0283(3) 0.0347(3) 0.0259(3) 0.00006(17) 0.00840(19) -0.00333(19) O4 0.0311(9) 0.0558(11) 0.0418(9) -0.0044(7) 0.0160(7) -0.0041(7) O2 0.0391(10) 0.0596(11) 0.0295(8) 0.0053(7) -0.0007(7) -0.0091(7) O1 0.0302(8) 0.0440(9) 0.0295(7) 0.0072(6) 0.0102(6) 0.0000(6) O3 0.0635(13) 0.0345(11) 0.0550(10) -0.0014(7) 0.0172(9) -0.0052(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 C1 1.340(3) . ? N1 N2 1.368(2) . ? N1 N6 1.387(2) . ? N6 H6A 0.82(3) . ? N6 H6B 0.89(4) . ? C1 N5 1.304(3) . ? C1 N4 1.333(3) . ? N4 N3 1.361(3) . ? N4 H4 0.79(3) . ? N5 H5A 0.85(3) . ? N5 H5B 0.88(3) . ? N3 N2 1.272(3) . ? Cl1 O3 1.4190(19) . ? Cl1 O4 1.4304(19) . ? Cl1 O2 1.4394(16) . ? Cl1 O1 1.4580(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 N2 110.35(16) . . ? C1 N1 N6 123.51(17) . . ? N2 N1 N6 125.99(18) . . ? N1 N6 H6A 107(2) . . ? N1 N6 H6B 107.0(19) . . ? H6A N6 H6B 101(3) . . ? N5 C1 N4 129.2(2) . . ? N5 C1 N1 127.1(2) . . ? N4 C1 N1 103.68(18) . . ? C1 N4 N3 110.59(19) . . ? C1 N4 H4 127(2) . . ? N3 N4 H4 122(2) . . ? C1 N5 H5A 120(2) . . ? C1 N5 H5B 121.3(17) . . ? H5A N5 H5B 118(3) . . ? N2 N3 N4 108.00(17) . . ? N3 N2 N1 107.38(17) . . ? O3 Cl1 O4 110.87(11) . . ? O3 Cl1 O2 110.33(11) . . ? O4 Cl1 O2 109.62(11) . . ? O3 Cl1 O1 109.33(11) . . ? O4 Cl1 O1 109.19(10) . . ? O2 Cl1 O1 107.42(10) . . ? _refine_diff_density_max 0.360 _refine_diff_density_min -0.415 _refine_diff_density_rms 0.070 _exptl_crystal_recrystallization_method 'from conc. MeOH solutions overlayerd with Et2O'