# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'John Holbrey' 'Alan R. Katritzky' 'Kostyantyn Kirichenko' 'W Matthew Reichert' 'Robin D. Rogers' 'Shailendra Singh' 'Marcin Smiglak' _publ_contact_author_name 'Dr John Holbrey' _publ_contact_author_address ; Center for Green Manufacturing and Department of Chemistry The University of Alabama Tuscaloosa Alabama 35487 UNITED STATES OF AMERICA ; _publ_contact_author_email JHOLBREY@BAMA.UA.EDU _publ_requested_journal 'Chemical Communications' _publ_section_title ; 1-Butyl-3-methylimidazolium 3,5-dinitro-1,2,4-triazolate: A novel ionic liquid containing a rigid, planar energetic anion ; data_w1 _database_code_depnum_ccdc_archive 'CCDC 252733' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H20 N6 O4' _chemical_formula_weight 288.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.9962(17) _cell_length_b 12.148(3) _cell_length_c 16.572(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1408.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 981 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 23.28 _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.84 _exptl_crystal_size_mid 0.76 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6325 _diffrn_reflns_av_R_equivalents 0.0145 _diffrn_reflns_av_sigmaI/netI 0.0138 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 23.29 _reflns_number_total 2022 _reflns_number_gt 1958 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0276P)^2^+0.1286P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0233(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00 _refine_ls_number_reflns 2022 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0208 _refine_ls_R_factor_gt 0.0198 _refine_ls_wR_factor_ref 0.0491 _refine_ls_wR_factor_gt 0.0486 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.002 _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 N2 N 0.27776(15) 0.54866(9) 0.72796(6) 0.0281(2) Uani 1 1 d . . . N3 N 0.20224(16) 0.56468(9) 0.86072(6) 0.0326(3) Uani 1 1 d . . . N4 N 0.25143(15) 0.66661(9) 0.83395(6) 0.0326(3) Uani 1 1 d . . . N5 N 0.35587(15) 0.74078(8) 0.70558(6) 0.0298(3) Uani 1 1 d . . . N6 N 0.17086(16) 0.38459(9) 0.79908(7) 0.0351(3) Uani 1 1 d . . . O1 O 0.35393(18) 0.83372(8) 0.73316(6) 0.0544(3) Uani 1 1 d . . . O2 O 0.40892(16) 0.71950(8) 0.63710(5) 0.0415(3) Uani 1 1 d . . . O3 O 0.19334(17) 0.32961(8) 0.73840(6) 0.0527(3) Uani 1 1 d . . . O4 O 0.10566(17) 0.34896(9) 0.86264(6) 0.0504(3) Uani 1 1 d . . . C9 C 0.29376(17) 0.65086(10) 0.75641(7) 0.0259(3) Uani 1 1 d . . . C10 C 0.22029(17) 0.50097(10) 0.79573(7) 0.0274(3) Uani 1 1 d . . . N1 N 0.78128(14) 0.49027(8) 0.54023(6) 0.0229(2) Uani 1 1 d . . . C1 C 0.84582(19) 0.60345(11) 0.51358(9) 0.0313(3) Uani 1 1 d . . . H1A H 0.7931(18) 0.6136(11) 0.4588(8) 0.025(3) Uiso 1 1 d . . . H1B H 0.782(2) 0.6556(12) 0.5499(9) 0.033(4) Uiso 1 1 d . . . C2 C 1.0595(2) 0.62088(15) 0.51394(10) 0.0420(4) Uani 1 1 d . . . H2A H 1.120(3) 0.5756(15) 0.4747(12) 0.057(5) Uiso 1 1 d . . . H2B H 1.114(3) 0.6129(15) 0.5691(11) 0.053(5) Uiso 1 1 d . . . H2C H 1.078(3) 0.6981(18) 0.4972(11) 0.070(6) Uiso 1 1 d . . . C3 C 0.85909(19) 0.40160(12) 0.48485(8) 0.0287(3) Uani 1 1 d . . . H3A H 0.998(2) 0.4057(10) 0.4893(7) 0.021(3) Uiso 1 1 d . . . H3B H 0.8191(19) 0.3346(12) 0.5095(8) 0.026(3) Uiso 1 1 d . . . C4 C 0.7976(2) 0.41025(15) 0.39790(8) 0.0396(4) Uani 1 1 d . . . H4A H 0.839(3) 0.4772(16) 0.3728(11) 0.058(5) Uiso 1 1 d . . . H4B H 0.851(2) 0.3451(14) 0.3665(10) 0.051(4) Uiso 1 1 d . . . H4C H 0.659(3) 0.4065(15) 0.3916(10) 0.056(5) Uiso 1 1 d . . . C5 C 0.56368(17) 0.49122(11) 0.53859(8) 0.0263(3) Uani 1 1 d . . . H5A H 0.5307(19) 0.5133(11) 0.4835(9) 0.026(3) Uiso 1 1 d . . . H5B H 0.525(2) 0.5506(12) 0.5768(8) 0.030(4) Uiso 1 1 d . . . C6 C 0.4715(2) 0.38346(14) 0.55954(10) 0.0396(4) Uani 1 1 d . . . H6A H 0.339(3) 0.3936(15) 0.5566(11) 0.061(5) Uiso 1 1 d . . . H6B H 0.496(3) 0.3276(16) 0.5185(11) 0.058(5) Uiso 1 1 d . . . H6C H 0.506(3) 0.3578(16) 0.6125(12) 0.065(5) Uiso 1 1 d . . . C7 C 0.85552(19) 0.46423(11) 0.62427(7) 0.0252(3) Uani 1 1 d . . . H7A H 0.8089(17) 0.3928(11) 0.6363(7) 0.015(3) Uiso 1 1 d . . . H7B H 0.991(2) 0.4627(11) 0.6191(8) 0.027(3) Uiso 1 1 d . . . C8 C 0.7966(2) 0.54565(12) 0.68850(8) 0.0330(3) Uani 1 1 d . . . H8A H 0.845(2) 0.5192(12) 0.7390(10) 0.037(4) Uiso 1 1 d . . . H8B H 0.847(2) 0.6193(14) 0.6766(9) 0.043(4) Uiso 1 1 d . . . H8C H 0.659(3) 0.5467(13) 0.6959(10) 0.050(5) 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 N2 0.0293(6) 0.0280(6) 0.0270(5) -0.0007(5) -0.0005(5) 0.0022(4) N3 0.0324(6) 0.0357(6) 0.0298(6) 0.0008(5) 0.0018(5) -0.0001(5) N4 0.0342(6) 0.0342(6) 0.0295(6) -0.0034(5) 0.0034(5) 0.0005(5) N5 0.0325(6) 0.0266(6) 0.0303(6) -0.0029(5) 0.0013(5) 0.0020(4) N6 0.0378(7) 0.0339(6) 0.0335(6) 0.0053(6) -0.0020(5) -0.0018(5) O1 0.0877(8) 0.0275(5) 0.0480(6) -0.0082(5) 0.0184(6) -0.0065(5) O2 0.0618(7) 0.0343(5) 0.0284(5) 0.0003(4) 0.0099(5) 0.0030(5) O3 0.0814(8) 0.0332(5) 0.0434(6) -0.0042(5) 0.0059(6) -0.0067(6) O4 0.0658(7) 0.0435(6) 0.0418(6) 0.0112(5) 0.0062(5) -0.0111(5) C9 0.0235(6) 0.0282(7) 0.0260(6) -0.0007(5) 0.0006(5) 0.0020(5) C10 0.0247(6) 0.0299(6) 0.0274(6) 0.0008(5) -0.0018(5) 0.0011(5) N1 0.0240(5) 0.0211(5) 0.0237(5) 0.0018(4) -0.0011(4) 0.0010(4) C1 0.0374(7) 0.0245(7) 0.0320(7) 0.0065(6) -0.0045(6) -0.0057(6) C2 0.0410(8) 0.0434(9) 0.0416(9) 0.0093(8) -0.0020(8) -0.0152(7) C3 0.0279(7) 0.0293(7) 0.0289(7) -0.0043(6) 0.0008(5) 0.0054(6) C4 0.0349(8) 0.0547(10) 0.0293(7) -0.0101(7) -0.0015(6) 0.0071(8) C5 0.0246(6) 0.0283(7) 0.0260(7) -0.0027(6) -0.0022(5) 0.0033(5) C6 0.0295(8) 0.0434(9) 0.0459(9) 0.0043(8) -0.0006(7) -0.0074(7) C7 0.0249(7) 0.0262(7) 0.0245(6) 0.0037(5) -0.0013(5) 0.0010(5) C8 0.0339(8) 0.0384(8) 0.0266(7) -0.0033(6) -0.0004(6) 0.0006(6) _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 N2 C10 1.3261(16) . ? N2 C9 1.3328(17) . ? N3 C10 1.3323(17) . ? N3 N4 1.3597(16) . ? N4 C9 1.3326(16) . ? N5 O1 1.2181(14) . ? N5 O2 1.2217(14) . ? N5 C9 1.4462(17) . ? N6 O3 1.2173(15) . ? N6 O4 1.2267(15) . ? N6 C10 1.4566(18) . ? C9 C10 2.0012(18) . ? N1 C1 1.5132(17) . ? N1 C3 1.5162(16) . ? N1 C7 1.5197(16) . ? N1 C5 1.5226(17) . ? C1 C2 1.510(2) . ? C3 C4 1.507(2) . ? C5 C6 1.500(2) . ? C7 C8 1.5106(19) . ? 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 C10 N2 C9 97.64(10) . . ? C10 N3 N4 103.97(10) . . ? C9 N4 N3 103.89(10) . . ? O1 N5 O2 123.23(11) . . ? O1 N5 C9 118.58(10) . . ? O2 N5 C9 118.19(10) . . ? O3 N6 O4 124.31(12) . . ? O3 N6 C10 118.06(11) . . ? O4 N6 C10 117.61(11) . . ? N4 C9 N2 117.14(11) . . ? N4 C9 N5 121.33(11) . . ? N2 C9 N5 121.53(10) . . ? N4 C9 C10 76.09(8) . . ? N2 C9 C10 41.05(7) . . ? N5 C9 C10 162.58(10) . . ? N2 C10 N3 117.36(11) . . ? N2 C10 N6 121.89(11) . . ? N3 C10 N6 120.71(11) . . ? N2 C10 C9 41.31(7) . . ? N3 C10 C9 76.05(8) . . ? N6 C10 C9 163.06(10) . . ? C1 N1 C3 111.21(10) . . ? C1 N1 C7 110.77(9) . . ? C3 N1 C7 106.50(9) . . ? C1 N1 C5 106.63(9) . . ? C3 N1 C5 110.71(9) . . ? C7 N1 C5 111.07(9) . . ? C2 C1 N1 114.94(12) . . ? C4 C3 N1 115.26(11) . . ? C6 C5 N1 114.79(11) . . ? C8 C7 N1 114.59(11) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 23.29 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.115 _refine_diff_density_min -0.090 _refine_diff_density_rms 0.025