# Electronic Supplementary Material for PCCP # This journal is (c) The Owner Societies 2008 data_cx347a _publ_contact_author_name 'Thomas M. Klapo\"tke' _publ_contact_author_address ; Department Chemie Ludwig-Maximilians Universit\"at Butenandtstra\&se 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; _publ_author_name 'Klap\"otke, Thomas M.' _publ_author_address ; Klap\"otke, Thomas M. Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland Stierstorfer, Joerg Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; _publ_contact_author_email 'tmk@cup.uni-muenchen.de' _publ_contact_author_fax '+49-89-2180-77491' _publ_contact_author_phone '+49-89-2180-77492' _publ_requested_journal ? _publ_section_title ;Crystal Structures of ; _publ_section_abstract ? _publ_section_comment ? _audit_author_name 'Joerg Stierstorfer' _audit_block_code ? _audit_creation_method SHELXL-97 _audit_creation_date ; 'Sat Oct 20 15:29:23 2007' ; _audit_update_record '21.10.2007' _chemical_name_systematic 'triaminoguanidinium dinitramide' _chemical_compound_source ? _chemical_name_common 'triaminoguanidinium dinitramide' _chemical_formula_moiety 'C H9 N6, N3 O4' _chemical_formula_sum 'C H9 N9 O4' _chemical_formula_weight 211.17 _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 18469 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.84 _diffrn_reflns_theta_max 27.50 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _reflns_number_total 1986 _reflns_number_gt 1419 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 -0.0304324280 _diffrn_orient_matrix_UB_12 0.0043410068 _diffrn_orient_matrix_UB_13 0.0390255397 _diffrn_orient_matrix_UB_21 -0.0446766353 _diffrn_orient_matrix_UB_22 -0.0482547155 _diffrn_orient_matrix_UB_23 -0.0050113566 _diffrn_orient_matrix_UB_31 0.0688153909 _diffrn_orient_matrix_UB_32 -0.0293487841 _diffrn_orient_matrix_UB_33 0.0140293630 _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' '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+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 12.5217(3) _cell_length_b 8.1036(2) _cell_length_c 16.9859(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1723.57(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6810 _cell_measurement_theta_min 3.8189 _cell_measurement_theta_max 32.5883 _cell_special_details ? _exptl_crystal_description rods _exptl_crystal_colour colorless _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.628 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.150 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.94841 _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 0.249 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.046 _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 1986 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0306 _refine_ls_wR_factor_ref 0.0891 _refine_ls_wR_factor_gt 0.0775 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 O3 O 0.43706(8) 0.32572(10) 0.18016(5) 0.0217(2) Uani 1 1 d . . . O1 O 0.44470(8) 0.01727(11) 0.17796(5) 0.0237(2) Uani 1 1 d . . . O4 O 0.40129(8) 0.43270(12) 0.06709(5) 0.0261(3) Uani 1 1 d . . . O2 O 0.34146(8) -0.09147(12) 0.09036(6) 0.0270(3) Uani 1 1 d . . . N1 N 0.35331(9) 0.16566(14) 0.32805(7) 0.0187(3) Uani 1 1 d . . . N5 N 0.17477(10) 0.19927(15) 0.30256(6) 0.0213(3) Uani 1 1 d . . . N7 N 0.37103(9) 0.17036(13) 0.07634(6) 0.0194(3) Uani 1 1 d . . . N3 N 0.24378(10) 0.27541(15) 0.42247(6) 0.0220(3) Uani 1 1 d . . . N2 N 0.44025(9) 0.20205(17) 0.37765(7) 0.0216(3) Uani 1 1 d . . . N6 N 0.19339(10) 0.13976(17) 0.22598(7) 0.0223(3) Uani 1 1 d . . . N9 N 0.40669(8) 0.31267(13) 0.11147(6) 0.0176(3) Uani 1 1 d . . . N8 N 0.38758(9) 0.02991(13) 0.11904(6) 0.0184(3) Uani 1 1 d . . . N4 N 0.13887(10) 0.31370(17) 0.44656(7) 0.0248(3) Uani 1 1 d . . . C1 C 0.25736(10) 0.21434(16) 0.35098(7) 0.0166(3) Uani 1 1 d . . . H3 H 0.2972(13) 0.2777(19) 0.4535(9) 0.028(4) Uiso 1 1 d . . . H6A H 0.1744(14) 0.218(2) 0.1932(10) 0.038(5) Uiso 1 1 d . . . H1 H 0.3651(14) 0.1427(18) 0.2797(10) 0.031(4) Uiso 1 1 d . . . H4A H 0.1257(13) 0.244(2) 0.4874(10) 0.031(4) Uiso 1 1 d . . . H2A H 0.4806(15) 0.277(2) 0.3518(10) 0.038(5) Uiso 1 1 d . . . H2B H 0.4787(14) 0.114(2) 0.3843(9) 0.031(4) Uiso 1 1 d . . . H5 H 0.1164(14) 0.2251(19) 0.3163(9) 0.027(4) Uiso 1 1 d . . . H4B H 0.1432(13) 0.415(2) 0.4655(10) 0.034(5) Uiso 1 1 d . . . H6B H 0.1499(13) 0.052(2) 0.2193(9) 0.028(4) 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 O3 0.0268(6) 0.0229(5) 0.0156(5) -0.0018(4) -0.0038(4) -0.0008(4) O1 0.0294(6) 0.0226(5) 0.0191(5) 0.0003(4) -0.0073(4) 0.0060(4) O4 0.0284(6) 0.0228(5) 0.0269(5) 0.0094(4) -0.0052(4) -0.0008(4) O2 0.0279(6) 0.0214(5) 0.0318(6) -0.0071(4) -0.0021(4) -0.0042(4) N1 0.0153(6) 0.0275(6) 0.0132(6) -0.0036(5) -0.0008(4) 0.0003(5) N5 0.0144(6) 0.0333(7) 0.0162(6) -0.0060(5) -0.0005(5) 0.0041(5) N7 0.0227(6) 0.0195(6) 0.0159(6) 0.0003(4) -0.0038(5) -0.0012(5) N3 0.0152(6) 0.0352(7) 0.0158(6) -0.0054(5) -0.0018(5) 0.0057(5) N2 0.0149(6) 0.0277(7) 0.0222(6) -0.0003(5) -0.0029(5) -0.0013(5) N6 0.0213(6) 0.0302(7) 0.0155(6) -0.0048(5) -0.0024(5) 0.0010(6) N9 0.0142(5) 0.0207(6) 0.0180(6) 0.0011(5) 0.0004(4) 0.0010(4) N8 0.0180(6) 0.0194(6) 0.0180(6) -0.0027(5) 0.0023(5) 0.0019(4) N4 0.0205(6) 0.0358(8) 0.0182(6) -0.0024(6) 0.0035(5) 0.0083(5) C1 0.0169(7) 0.0166(6) 0.0162(6) 0.0019(5) 0.0003(5) -0.0004(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 O3 N9 1.2318(13) . ? O1 N8 1.2345(14) . ? O4 N9 1.2324(13) . ? O2 N8 1.2403(14) . ? N1 C1 1.3231(17) . ? N1 N2 1.4077(16) . ? N1 H1 0.856(17) . ? N5 C1 1.3270(17) . ? N5 N6 1.4067(16) . ? N5 H5 0.795(17) . ? N7 N8 1.3655(14) . ? N7 N9 1.3731(14) . ? N3 C1 1.3223(16) . ? N3 N4 1.4104(16) . ? N3 H3 0.851(16) . ? N2 H2A 0.904(19) . ? N2 H2B 0.870(18) . ? N6 H6A 0.877(18) . ? N6 H6B 0.901(17) . ? N4 H4A 0.912(17) . ? N4 H4B 0.880(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 C1 N1 N2 117.62(11) . . ? C1 N1 H1 120.3(12) . . ? N2 N1 H1 119.1(12) . . ? C1 N5 N6 118.39(12) . . ? C1 N5 H5 120.6(11) . . ? N6 N5 H5 121.0(11) . . ? N8 N7 N9 114.83(10) . . ? C1 N3 N4 117.93(12) . . ? C1 N3 H3 118.4(10) . . ? N4 N3 H3 123.2(10) . . ? N1 N2 H2A 106.4(11) . . ? N1 N2 H2B 109.5(11) . . ? H2A N2 H2B 107.9(16) . . ? N5 N6 H6A 107.1(11) . . ? N5 N6 H6B 106.6(10) . . ? H6A N6 H6B 108.9(15) . . ? O3 N9 O4 121.91(11) . . ? O3 N9 N7 125.74(10) . . ? O4 N9 N7 112.28(10) . . ? O1 N8 O2 121.49(10) . . ? O1 N8 N7 126.00(10) . . ? O2 N8 N7 112.44(10) . . ? N3 N4 H4A 104.6(10) . . ? N3 N4 H4B 104.7(10) . . ? H4A N4 H4B 108.2(15) . . ? N3 C1 N1 119.91(12) . . ? N3 C1 N5 120.23(13) . . ? N1 C1 N5 119.86(12) . . ? 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 N8 N7 N9 O3 -10.74(18) . . . . ? N8 N7 N9 O4 172.12(10) . . . . ? N9 N7 N8 O1 -12.11(18) . . . . ? N9 N7 N8 O2 170.73(10) . . . . ? N4 N3 C1 N1 -175.15(12) . . . . ? N4 N3 C1 N5 3.78(19) . . . . ? N2 N1 C1 N3 -8.46(19) . . . . ? N2 N1 C1 N5 172.61(12) . . . . ? N6 N5 C1 N3 177.56(13) . . . . ? N6 N5 C1 N1 -3.51(19) . . . . ? 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 N3 H3 N7 0.851(16) 2.321(15) 3.0923(16) 150.8(14) 8_566 N6 H6A O2 0.877(18) 2.340(19) 3.2001(17) 167.0(15) 7_665 N1 H1 O1 0.856(17) 2.238(17) 3.0422(15) 156.5(15) . N1 H1 O3 0.856(17) 2.422(16) 3.0154(15) 127.0(12) . N4 H4A O2 0.912(17) 2.178(18) 3.0447(16) 158.3(14) 2 N2 H2A O1 0.904(19) 2.218(19) 3.0810(16) 159.4(15) 4_655 N2 H2A O2 0.904(19) 2.658(18) 3.2506(16) 123.9(13) 4_655 N2 H2A N8 0.904(19) 2.678(18) 3.4220(17) 140.3(13) 4_655 N2 H2B O4 0.870(18) 2.257(18) 3.0956(16) 162.0(14) 4_645 N5 H5 O3 0.795(17) 2.390(17) 3.1616(15) 163.9(15) 6_556 N4 H4B O4 0.880(17) 2.195(17) 2.9441(15) 142.7(14) 2_565 N6 H6B O3 0.901(17) 2.236(17) 3.1226(16) 167.9(13) 7_655 _geom_special_details ?