# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'J M Shreeve' _publ_contact_author_email JSHREEVE@UIDAHO.EDU _publ_section_title ; Nitrogen-rich Nitroguanidine-functionalized Tetrazolate Energetic Salts ; loop_ _publ_author_name 'J M Shreeve' 'Yong Guo' 'Ruihu Wang' 'Zhuo Zeng' # Attachment '713770.cif' data_shrv08 _database_code_depnum_ccdc_archive 'CCDC 713770' _audit_creation_date 2008-08-01 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; 1,4-dimethyl-tetrazol-5-iminium 2-nitro-1-(tetrazol-5-yl)guanidide ; _chemical_name_common ;1,4-dimethyl-tetrazol-5-iminium 2-nitro-1-(tetrazol-5- yl)guanidide ; _chemical_melting_point ? _chemical_formula_moiety 'C3 H8 N5 +1, C2 H3 N8 O2 -1' _chemical_formula_sum 'C5 H11 N13 O2' _chemical_formula_weight 285.27 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' _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 7.5851(4) _cell_length_b 7.8340(4) _cell_length_c 10.1061(5) _cell_angle_alpha 92.953(2) _cell_angle_beta 98.725(2) _cell_angle_gamma 98.728(2) _cell_volume 584.99(5) _cell_formula_units_Z 2 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 4318 _cell_measurement_theta_min 2.752 _cell_measurement_theta_max 28.283 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.620 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2004/1 (Bruker, 2004)' _exptl_absorpt_correction_T_min 0.7525 _exptl_absorpt_correction_T_max 1.0000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6394 _diffrn_reflns_av_R_equivalents 0.0113 _diffrn_reflns_av_sigmaI/netI 0.0141 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 28.41 _reflns_number_total 2889 _reflns_number_gt 2635 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2 v2.1-0 (Bruker, 2006)' _computing_cell_refinement 'Bruker APEX2 v2.1-0 (Bruker, 2006)' _computing_data_reduction ; Bruker SAINT v7.34A (Bruker, 2002), Bruker XPREP v6.12 (Bruker, 2001) ; _computing_structure_solution 'Bruker SHELXTL v6.12 (Bruker, 2000b)' _computing_structure_refinement 'Bruker SHELXTL v6.12 (Bruker, 2000b)' _computing_molecular_graphics 'Bruker SHELXTL v6.12 (Bruker, 2000b)' _computing_publication_material 'Bruker SHELXTL v6.12 (Bruker, 2000b)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0590P)^2^+0.1712P] 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 2889 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0394 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.1031 _refine_ls_wR_factor_gt 0.1000 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 0.05730(14) 0.78196(13) -0.09868(10) 0.0181(2) Uani 1 1 d . . . N2 N 0.08493(13) 0.65938(12) -0.18593(9) 0.0226(2) Uani 1 1 d . . . N3 N 0.01074(13) 0.70502(12) -0.30664(9) 0.0244(2) Uani 1 1 d . . . N4 N -0.05718(13) 0.84682(12) -0.28979(9) 0.0221(2) Uani 1 1 d . . . N5 N -0.03010(12) 0.90088(12) -0.15735(9) 0.0207(2) Uani 1 1 d . . . N6 N 0.11313(13) 0.79105(12) 0.03959(9) 0.0204(2) Uani 1 1 d . . . H6A H 0.0861 0.8772 0.0879 0.024 Uiso 1 1 calc R . . N7 N 0.24923(13) 0.54520(12) 0.03886(9) 0.0230(2) Uani 1 1 d . . . H7A H 0.2181 0.5297 -0.0489 0.028 Uiso 1 1 calc R . . H7B H 0.3095 0.4721 0.0824 0.028 Uiso 1 1 calc R . . C7 C 0.20544(14) 0.67828(13) 0.10537(10) 0.0186(2) Uani 1 1 d . . . N8 N 0.24303(12) 0.72397(11) 0.23996(9) 0.0208(2) Uani 1 1 d . . . N9 N 0.33363(13) 0.62227(12) 0.31878(9) 0.0219(2) Uani 1 1 d . . . O9A O 0.36863(13) 0.67385(11) 0.44060(8) 0.0310(2) Uani 1 1 d . . . O9B O 0.38347(13) 0.48740(11) 0.27865(9) 0.0299(2) Uani 1 1 d . . . N10 N 0.26429(13) -0.00112(12) 0.51169(9) 0.0224(2) Uani 1 1 d . . . H10A H 0.2071 0.0538 0.4491 0.027 Uiso 1 1 calc R . . H10B H 0.3001 -0.0991 0.4902 0.027 Uiso 1 1 calc R . . C10 C 0.29633(14) 0.06349(13) 0.63781(10) 0.0189(2) Uani 1 1 d . . . N11 N 0.25059(13) 0.21061(12) 0.68635(9) 0.0213(2) Uani 1 1 d . . . C11 C 0.16592(18) 0.33884(15) 0.61139(11) 0.0280(3) Uani 1 1 d . . . H11A H 0.0511 0.2828 0.5579 0.042 Uiso 1 1 calc R . . H11B H 0.2463 0.3904 0.5517 0.042 Uiso 1 1 calc R . . H11C H 0.1435 0.4296 0.6742 0.042 Uiso 1 1 calc R . . N12 N 0.30778(14) 0.23405(13) 0.82194(9) 0.0251(2) Uani 1 1 d . . . N13 N 0.38683(13) 0.10734(13) 0.85762(9) 0.0251(2) Uani 1 1 d . . . N14 N 0.38155(12) -0.00084(12) 0.74629(9) 0.0216(2) Uani 1 1 d . . . C14 C 0.47495(16) -0.15089(16) 0.75251(12) 0.0274(2) Uani 1 1 d . . . H14A H 0.4005 -0.2483 0.6953 0.041 Uiso 1 1 calc R . . H14B H 0.4960 -0.1829 0.8454 0.041 Uiso 1 1 calc R . . H14C H 0.5911 -0.1221 0.7210 0.041 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 C1 0.0198(4) 0.0153(4) 0.0189(5) -0.0012(3) 0.0031(4) 0.0035(3) N2 0.0298(5) 0.0208(4) 0.0179(4) -0.0025(3) 0.0020(3) 0.0094(4) N3 0.0313(5) 0.0231(5) 0.0196(4) -0.0018(3) 0.0017(4) 0.0108(4) N4 0.0261(4) 0.0212(4) 0.0192(4) -0.0017(3) 0.0019(3) 0.0072(3) N5 0.0251(4) 0.0190(4) 0.0184(4) -0.0017(3) 0.0016(3) 0.0071(3) N6 0.0280(5) 0.0170(4) 0.0169(4) -0.0031(3) 0.0020(3) 0.0088(3) N7 0.0305(5) 0.0189(4) 0.0201(4) -0.0023(3) 0.0011(4) 0.0102(4) C7 0.0204(5) 0.0148(4) 0.0201(5) -0.0011(3) 0.0034(4) 0.0022(4) N8 0.0272(5) 0.0165(4) 0.0191(4) -0.0001(3) 0.0018(3) 0.0069(3) N9 0.0271(5) 0.0174(4) 0.0210(4) -0.0001(3) 0.0018(3) 0.0056(3) O9A 0.0475(5) 0.0270(4) 0.0183(4) -0.0018(3) -0.0025(3) 0.0141(4) O9B 0.0420(5) 0.0221(4) 0.0274(4) -0.0009(3) 0.0002(3) 0.0171(3) N10 0.0310(5) 0.0193(4) 0.0182(4) -0.0015(3) 0.0031(3) 0.0098(4) C10 0.0199(5) 0.0166(5) 0.0202(5) 0.0001(4) 0.0040(4) 0.0026(4) N11 0.0274(4) 0.0189(4) 0.0172(4) -0.0026(3) 0.0027(3) 0.0050(3) C11 0.0406(6) 0.0213(5) 0.0234(5) -0.0019(4) 0.0010(5) 0.0142(5) N12 0.0311(5) 0.0254(5) 0.0174(4) -0.0031(3) 0.0026(4) 0.0033(4) N13 0.0282(5) 0.0262(5) 0.0197(4) -0.0015(4) 0.0025(4) 0.0032(4) N14 0.0232(4) 0.0219(5) 0.0195(4) 0.0011(3) 0.0018(3) 0.0045(3) C14 0.0280(5) 0.0279(6) 0.0291(6) 0.0066(4) 0.0046(4) 0.0118(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 N2 1.3317(13) . ? C1 N5 1.3357(13) . ? C1 N6 1.3921(13) . ? N2 N3 1.3530(12) . ? N3 N4 1.3074(13) . ? N4 N5 1.3582(12) . ? N6 C7 1.3490(13) . ? N6 H6A 0.8800 . ? N7 C7 1.3228(13) . ? N7 H7A 0.8800 . ? N7 H7B 0.8800 . ? C7 N8 1.3641(13) . ? N8 N9 1.3443(12) . ? N9 O9B 1.2439(12) . ? N9 O9A 1.2515(12) . ? N10 C10 1.3199(13) . ? N10 H10A 0.8800 . ? N10 H10B 0.8800 . ? C10 N11 1.3432(13) . ? C10 N14 1.3470(13) . ? N11 N12 1.3671(12) . ? N11 C11 1.4567(14) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? N12 N13 1.2755(14) . ? N13 N14 1.3651(13) . ? N14 C14 1.4610(14) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 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 C1 N5 112.96(9) . . ? N2 C1 N6 125.17(10) . . ? N5 C1 N6 121.87(9) . . ? C1 N2 N3 104.15(9) . . ? N4 N3 N2 109.41(9) . . ? N3 N4 N5 110.09(8) . . ? C1 N5 N4 103.39(8) . . ? C7 N6 C1 125.17(9) . . ? C7 N6 H6A 117.4 . . ? C1 N6 H6A 117.4 . . ? C7 N7 H7A 120.0 . . ? C7 N7 H7B 120.0 . . ? H7A N7 H7B 120.0 . . ? N7 C7 N6 120.48(10) . . ? N7 C7 N8 128.36(10) . . ? N6 C7 N8 111.16(9) . . ? N9 N8 C7 117.84(9) . . ? O9B N9 O9A 120.30(9) . . ? O9B N9 N8 124.94(9) . . ? O9A N9 N8 114.76(9) . . ? C10 N10 H10A 120.0 . . ? C10 N10 H10B 120.0 . . ? H10A N10 H10B 120.0 . . ? N10 C10 N11 127.08(10) . . ? N10 C10 N14 128.53(10) . . ? N11 C10 N14 104.39(9) . . ? C10 N11 N12 109.76(9) . . ? C10 N11 C11 127.89(9) . . ? N12 N11 C11 122.19(9) . . ? N11 C11 H11A 109.5 . . ? N11 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N11 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N13 N12 N11 108.00(9) . . ? N12 N13 N14 108.25(9) . . ? C10 N14 N13 109.59(9) . . ? C10 N14 C14 128.79(9) . . ? N13 N14 C14 121.33(9) . . ? N14 C14 H14A 109.5 . . ? N14 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N14 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 N5 C1 N2 N3 0.24(12) . . . . ? N6 C1 N2 N3 -179.08(10) . . . . ? C1 N2 N3 N4 -0.26(12) . . . . ? N2 N3 N4 N5 0.20(12) . . . . ? N2 C1 N5 N4 -0.12(12) . . . . ? N6 C1 N5 N4 179.22(9) . . . . ? N3 N4 N5 C1 -0.05(12) . . . . ? N2 C1 N6 C7 0.89(17) . . . . ? N5 C1 N6 C7 -178.37(10) . . . . ? C1 N6 C7 N7 -0.50(16) . . . . ? C1 N6 C7 N8 178.91(9) . . . . ? N7 C7 N8 N9 -1.15(16) . . . . ? N6 C7 N8 N9 179.49(9) . . . . ? C7 N8 N9 O9B -1.29(16) . . . . ? C7 N8 N9 O9A 177.97(9) . . . . ? N10 C10 N11 N12 -179.75(10) . . . . ? N14 C10 N11 N12 0.05(11) . . . . ? N10 C10 N11 C11 -4.29(18) . . . . ? N14 C10 N11 C11 175.50(11) . . . . ? C10 N11 N12 N13 0.18(12) . . . . ? C11 N11 N12 N13 -175.58(10) . . . . ? N11 N12 N13 N14 -0.33(12) . . . . ? N10 C10 N14 N13 179.54(10) . . . . ? N11 C10 N14 N13 -0.25(11) . . . . ? N10 C10 N14 C14 5.81(18) . . . . ? N11 C10 N14 C14 -173.98(10) . . . . ? N12 N13 N14 C10 0.37(12) . . . . ? N12 N13 N14 C14 174.65(10) . . . . ? 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 H6A N5 0.88 1.97 2.8338(12) 166.4 2_575 N7 H7A N2 0.88 2.00 2.6838(13) 133.6 . N7 H7B O9B 0.88 1.97 2.5727(12) 124.5 . N10 H10A N4 0.88 2.08 2.9572(13) 172.8 2_565 N10 H10B O9A 0.88 1.99 2.8674(12) 177.2 1_545 _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.284 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.061 # Attachment '713771.cif' data_shrv07 _database_code_depnum_ccdc_archive 'CCDC 713771' _audit_creation_date 2008-07-31 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; 5-(nitroimino)hexahydroimidazo[4,5]imidazol-2-iminium 5-(2-nitroguanidino)tetrazol-1-ide hydrate ; _chemical_name_common ; 5-(nitroimino)hexahydroimidazo(4,5)imidazol-2-iminium 5-(2- nitroguanidino)tetrazol-1-ide hydrate ; _chemical_melting_point ? _chemical_formula_moiety 'C4 H8 N7 O2 1+, C2 H3 N8 O2 1-, H2 O1' _chemical_formula_sum 'C6 H13 N15 O5' _chemical_formula_weight 375.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2741(4) _cell_length_b 8.4920(4) _cell_length_c 11.3507(8) _cell_angle_alpha 102.566(2) _cell_angle_beta 98.514(2) _cell_angle_gamma 108.446(2) _cell_volume 717.90(7) _cell_formula_units_Z 2 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 4558 _cell_measurement_theta_min 2.667 _cell_measurement_theta_max 28.287 _exptl_crystal_description irregular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.77 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.736 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.149 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2004/1 (Bruker, 2004)' _exptl_absorpt_correction_T_min 0.7746 _exptl_absorpt_correction_T_max 1.0000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7955 _diffrn_reflns_av_R_equivalents 0.0124 _diffrn_reflns_av_sigmaI/netI 0.0162 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 28.39 _reflns_number_total 3522 _reflns_number_gt 3173 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2 v2.1-0 (Bruker, 2006)' _computing_cell_refinement 'Bruker APEX2 v2.1-0 (Bruker, 2006)' _computing_data_reduction ; Bruker SAINT v7.34A (Bruker, 2002), Bruker XPREP v6.12 (Bruker, 2001) ; _computing_structure_solution 'Bruker SHELXTL v6.12 (Bruker, 2000b)' _computing_structure_refinement 'Bruker SHELXTL v6.12 (Bruker, 2000b)' _computing_molecular_graphics 'Bruker SHELXTL v6.12 (Bruker, 2000b)' _computing_publication_material 'Bruker SHELXTL v6.12 (Bruker, 2000b)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0694P)^2^+0.3439P] 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 3522 _refine_ls_number_parameters 243 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1094 _refine_ls_wR_factor_gt 0.1059 _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_restrained_S_all 0.955 _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 C1 C 0.03243(15) 0.29625(15) 0.37750(11) 0.0161(2) Uani 1 1 d . . . N2 N -0.03658(14) 0.40729(14) 0.34431(9) 0.0194(2) Uani 1 1 d . . . N3 N -0.07664(14) 0.35343(15) 0.21892(10) 0.0214(2) Uani 1 1 d . . . N4 N -0.03300(14) 0.21898(15) 0.18158(10) 0.0221(2) Uani 1 1 d . . . N5 N 0.03854(14) 0.17884(14) 0.28068(9) 0.0205(2) Uani 1 1 d . . . N6 N 0.09081(14) 0.30810(13) 0.50139(9) 0.0174(2) Uani 1 1 d . . . H6A H 0.0773 0.3893 0.5577 0.021 Uiso 1 1 calc R . . N7 N 0.19360(14) 0.08292(14) 0.46286(9) 0.0191(2) Uani 1 1 d . . . H7A H 0.1620 0.0685 0.3826 0.023 Uiso 1 1 calc R . . H7B H 0.2432 0.0158 0.4900 0.023 Uiso 1 1 calc R . . C7 C 0.16678(15) 0.20454(15) 0.54218(11) 0.0159(2) Uani 1 1 d . . . N8 N 0.20515(14) 0.24601(13) 0.66927(9) 0.0183(2) Uani 1 1 d . . . N9 N 0.28506(14) 0.15728(14) 0.72335(10) 0.0192(2) Uani 1 1 d . . . O9A O 0.31761(14) 0.20065(13) 0.83919(8) 0.0263(2) Uani 1 1 d . . . O9B O 0.32838(13) 0.03966(13) 0.66668(9) 0.0265(2) Uani 1 1 d . . . C10 C 0.42624(15) 0.45018(15) 1.29863(11) 0.0167(2) Uani 1 1 d . . . N11 N 0.50290(14) 0.34807(14) 1.33779(10) 0.0197(2) Uani 1 1 d . . . H11A H 0.5479 0.3618 1.4162 0.024 Uiso 1 1 calc R . . C12 C 0.50304(15) 0.21255(15) 1.23593(11) 0.0181(2) Uani 1 1 d . . . H12A H 0.6230 0.2096 1.2364 0.022 Uiso 1 1 calc R . . N13 N 0.37516(14) 0.04394(13) 1.22550(9) 0.0183(2) Uani 1 1 d . . . H13A H 0.3776 -0.0123 1.2819 0.022 Uiso 1 1 calc R . . N14 N 0.12737(15) -0.16654(14) 1.08036(10) 0.0232(2) Uani 1 1 d . . . H14A H 0.1185 -0.2391 1.1260 0.028 Uiso 1 1 calc R . . H14B H 0.0516 -0.1963 1.0089 0.028 Uiso 1 1 calc R . . C14 C 0.25326(16) -0.01436(15) 1.11874(10) 0.0166(2) Uani 1 1 d . . . N15 N 0.27417(14) 0.10450(13) 1.05592(9) 0.0191(2) Uani 1 1 d . . . H15A H 0.2046 0.0903 0.9847 0.023 Uiso 1 1 calc R . . C16 C 0.42567(16) 0.25924(15) 1.11992(11) 0.0181(2) Uani 1 1 d . . . H16A H 0.5114 0.2874 1.0672 0.022 Uiso 1 1 calc R . . N17 N 0.38186(14) 0.40795(13) 1.17507(10) 0.0185(2) Uani 1 1 d . . . H17A H 0.3326 0.4625 1.1324 0.022 Uiso 1 1 calc R . . N18 N 0.40955(14) 0.57332(13) 1.38899(10) 0.0191(2) Uani 1 1 d . . . N19 N 0.33859(14) 0.68264(14) 1.35440(10) 0.0209(2) Uani 1 1 d . . . O20 O 0.32381(15) 0.78987(13) 1.44077(10) 0.0332(3) Uani 1 1 d . . . O21 O 0.29330(14) 0.67859(13) 1.24363(9) 0.0282(2) Uani 1 1 d . . . O1S O 0.21659(15) 0.47763(14) 0.95262(9) 0.0296(2) Uani 1 1 d D . . H1SA H 0.236(2) 0.3973(18) 0.9031(11) 0.045(6) Uiso 1 1 d D . . H1SB H 0.168(2) 0.524(2) 0.9044(12) 0.044(5) 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 0.0142(5) 0.0177(5) 0.0156(5) 0.0049(4) 0.0013(4) 0.0055(4) N2 0.0223(5) 0.0222(5) 0.0153(5) 0.0060(4) 0.0015(4) 0.0108(4) N3 0.0222(5) 0.0276(6) 0.0156(5) 0.0067(4) 0.0018(4) 0.0114(4) N4 0.0227(5) 0.0301(6) 0.0149(5) 0.0051(4) 0.0009(4) 0.0136(5) N5 0.0234(5) 0.0244(5) 0.0143(5) 0.0038(4) 0.0008(4) 0.0122(4) N6 0.0223(5) 0.0181(5) 0.0129(5) 0.0036(4) 0.0019(4) 0.0106(4) N7 0.0244(5) 0.0204(5) 0.0155(5) 0.0053(4) 0.0032(4) 0.0127(4) C7 0.0146(5) 0.0158(5) 0.0165(5) 0.0055(4) 0.0023(4) 0.0045(4) N8 0.0223(5) 0.0194(5) 0.0153(5) 0.0064(4) 0.0029(4) 0.0099(4) N9 0.0219(5) 0.0195(5) 0.0164(5) 0.0074(4) 0.0022(4) 0.0074(4) O9A 0.0363(5) 0.0294(5) 0.0148(4) 0.0095(4) 0.0022(4) 0.0133(4) O9B 0.0348(5) 0.0277(5) 0.0224(5) 0.0070(4) 0.0024(4) 0.0203(4) C10 0.0159(5) 0.0132(5) 0.0184(5) 0.0053(4) 0.0016(4) 0.0022(4) N11 0.0243(5) 0.0168(5) 0.0158(5) 0.0029(4) -0.0016(4) 0.0088(4) C12 0.0177(5) 0.0177(5) 0.0186(5) 0.0045(4) 0.0020(4) 0.0074(4) N13 0.0235(5) 0.0151(5) 0.0155(5) 0.0060(4) -0.0008(4) 0.0074(4) N14 0.0282(6) 0.0168(5) 0.0191(5) 0.0042(4) -0.0005(4) 0.0041(4) C14 0.0213(5) 0.0167(5) 0.0137(5) 0.0036(4) 0.0038(4) 0.0099(4) N15 0.0259(5) 0.0172(5) 0.0120(4) 0.0052(4) -0.0002(4) 0.0064(4) C16 0.0213(6) 0.0174(5) 0.0168(5) 0.0065(4) 0.0049(4) 0.0071(5) N17 0.0237(5) 0.0160(5) 0.0175(5) 0.0068(4) 0.0028(4) 0.0087(4) N18 0.0228(5) 0.0156(5) 0.0189(5) 0.0053(4) 0.0014(4) 0.0079(4) N19 0.0237(5) 0.0157(5) 0.0235(5) 0.0067(4) 0.0033(4) 0.0076(4) O20 0.0463(6) 0.0271(5) 0.0308(5) 0.0028(4) 0.0082(5) 0.0233(5) O21 0.0397(6) 0.0260(5) 0.0242(5) 0.0122(4) 0.0035(4) 0.0174(4) O1S 0.0426(6) 0.0290(5) 0.0224(5) 0.0091(4) 0.0062(4) 0.0194(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N5 1.3327(15) . ? C1 N2 1.3375(15) . ? C1 N6 1.3884(15) . ? N2 N3 1.3512(14) . ? N3 N4 1.3074(16) . ? N4 N5 1.3526(14) . ? N6 C7 1.3504(15) . ? N6 H6A 0.8800 . ? N7 C7 1.3138(15) . ? N7 H7A 0.8800 . ? N7 H7B 0.8800 . ? C7 N8 1.3705(15) . ? N8 N9 1.3335(14) . ? N9 O9B 1.2470(14) . ? N9 O9A 1.2485(13) . ? C10 N17 1.3325(15) . ? C10 N11 1.3357(15) . ? C10 N18 1.3532(16) . ? N11 C12 1.4434(15) . ? N11 H11A 0.8800 . ? C12 N13 1.4540(16) . ? C12 C16 1.5618(16) . ? C12 H12A 1.0000 . ? N13 C14 1.3386(15) . ? N13 H13A 0.8800 . ? N14 C14 1.3091(16) . ? N14 H14A 0.8800 . ? N14 H14B 0.8800 . ? C14 N15 1.3403(15) . ? N15 C16 1.4486(16) . ? N15 H15A 0.8800 . ? C16 N17 1.4598(15) . ? C16 H16A 1.0000 . ? N17 H17A 0.8800 . ? N18 N19 1.3402(14) . ? N19 O20 1.2340(15) . ? N19 O21 1.2473(14) . ? O1S H1SA 0.8601(10) . ? O1S H1SB 0.8601(10) . ? 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 N5 C1 N2 113.01(10) . . ? N5 C1 N6 125.46(11) . . ? N2 C1 N6 121.53(11) . . ? C1 N2 N3 103.64(10) . . ? N4 N3 N2 109.78(10) . . ? N3 N4 N5 109.97(10) . . ? C1 N5 N4 103.60(10) . . ? C7 N6 C1 125.00(10) . . ? C7 N6 H6A 117.5 . . ? C1 N6 H6A 117.5 . . ? C7 N7 H7A 120.0 . . ? C7 N7 H7B 120.0 . . ? H7A N7 H7B 120.0 . . ? N7 C7 N6 120.43(11) . . ? N7 C7 N8 128.66(11) . . ? N6 C7 N8 110.91(10) . . ? N9 N8 C7 117.77(10) . . ? O9B N9 O9A 120.09(10) . . ? O9B N9 N8 124.73(10) . . ? O9A N9 N8 115.17(10) . . ? N17 C10 N11 111.36(10) . . ? N17 C10 N18 133.04(11) . . ? N11 C10 N18 115.60(10) . . ? C10 N11 C12 111.86(10) . . ? C10 N11 H11A 124.1 . . ? C12 N11 H11A 124.1 . . ? N11 C12 N13 113.23(10) . . ? N11 C12 C16 102.63(9) . . ? N13 C12 C16 102.96(9) . . ? N11 C12 H12A 112.4 . . ? N13 C12 H12A 112.4 . . ? C16 C12 H12A 112.4 . . ? C14 N13 C12 111.05(10) . . ? C14 N13 H13A 124.5 . . ? C12 N13 H13A 124.5 . . ? C14 N14 H14A 120.0 . . ? C14 N14 H14B 120.0 . . ? H14A N14 H14B 120.0 . . ? N14 C14 N13 124.92(11) . . ? N14 C14 N15 123.73(11) . . ? N13 C14 N15 111.34(11) . . ? C14 N15 C16 111.48(10) . . ? C14 N15 H15A 124.3 . . ? C16 N15 H15A 124.3 . . ? N15 C16 N17 113.82(10) . . ? N15 C16 C12 102.82(9) . . ? N17 C16 C12 102.83(9) . . ? N15 C16 H16A 112.2 . . ? N17 C16 H16A 112.2 . . ? C12 C16 H16A 112.2 . . ? C10 N17 C16 111.07(10) . . ? C10 N17 H17A 124.5 . . ? C16 N17 H17A 124.5 . . ? N19 N18 C10 117.85(10) . . ? O20 N19 O21 122.34(11) . . ? O20 N19 N18 114.86(11) . . ? O21 N19 N18 122.79(11) . . ? H1SA O1S H1SB 104.47(17) . . ? 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 0.51(14) . . . . ? N6 C1 N2 N3 -179.84(11) . . . . ? C1 N2 N3 N4 -0.11(13) . . . . ? N2 N3 N4 N5 -0.30(14) . . . . ? N2 C1 N5 N4 -0.68(14) . . . . ? N6 C1 N5 N4 179.69(11) . . . . ? N3 N4 N5 C1 0.59(13) . . . . ? N5 C1 N6 C7 1.8(2) . . . . ? N2 C1 N6 C7 -177.83(11) . . . . ? C1 N6 C7 N7 1.25(19) . . . . ? C1 N6 C7 N8 -178.33(11) . . . . ? N7 C7 N8 N9 2.16(19) . . . . ? N6 C7 N8 N9 -178.32(10) . . . . ? C7 N8 N9 O9B 0.40(18) . . . . ? C7 N8 N9 O9A 179.72(10) . . . . ? N17 C10 N11 C12 -4.73(15) . . . . ? N18 C10 N11 C12 175.52(10) . . . . ? C10 N11 C12 N13 -104.92(12) . . . . ? C10 N11 C12 C16 5.33(13) . . . . ? N11 C12 N13 C14 116.08(11) . . . . ? C16 C12 N13 C14 6.02(13) . . . . ? C12 N13 C14 N14 175.83(11) . . . . ? C12 N13 C14 N15 -5.17(14) . . . . ? N14 C14 N15 C16 -179.21(11) . . . . ? N13 C14 N15 C16 1.78(14) . . . . ? C14 N15 C16 N17 -108.44(11) . . . . ? C14 N15 C16 C12 2.00(13) . . . . ? N11 C12 C16 N15 -122.42(10) . . . . ? N13 C12 C16 N15 -4.62(11) . . . . ? N11 C12 C16 N17 -3.95(11) . . . . ? N13 C12 C16 N17 113.84(10) . . . . ? N11 C10 N17 C16 1.76(14) . . . . ? N18 C10 N17 C16 -178.55(12) . . . . ? N15 C16 N17 C10 112.02(11) . . . . ? C12 C16 N17 C10 1.58(13) . . . . ? N17 C10 N18 N19 -1.8(2) . . . . ? N11 C10 N18 N19 177.88(11) . . . . ? C10 N18 N19 O20 178.70(11) . . . . ? C10 N18 N19 O21 -2.38(18) . . . . ? 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 H6A N2 0.88 1.99 2.8613(15) 168.1 2_566 N7 H7B O9B 0.88 1.97 2.5683(14) 124.2 . N7 H7B O20 0.88 2.21 2.9869(14) 146.7 1_544 N11 H11A N18 0.88 2.11 2.9524(15) 161.3 2_668 N11 H11A O20 0.88 2.59 3.3201(15) 141.6 2_668 N13 H13A O21 0.88 2.41 3.0193(14) 126.5 1_545 N13 H13A O9B 0.88 2.51 2.9343(14) 110.2 2_657 N14 H14A O21 0.88 2.20 2.9152(15) 138.2 1_545 N14 H14B N4 0.88 2.11 2.8573(16) 142.7 2_556 N15 H15A O9A 0.88 2.25 2.7924(13) 119.8 . N15 H15A N4 0.88 2.68 3.2421(15) 123.0 2_556 N17 H17A O21 0.88 2.14 2.6231(14) 114.3 . N17 H17A O1S 0.88 2.17 2.9555(14) 148.2 . O1S H1SA O9A 0.8601(10) 2.023(5) 2.8520(15) 161.6(15) . O1S H1SA N8 0.8601(10) 2.620(9) 3.3558(14) 144.2(13) . O1S H1SB N3 0.8601(10) 2.108(3) 2.9647(14) 173.8(19) 2_566 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.498 _refine_diff_density_min -0.481 _refine_diff_density_rms 0.065