# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2004 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_cambridge 0440 _audit_creation_date 10-05-02 _publ_contact_author_name ; Richard Welter ; _publ_contact_author_address ; Institut Le Bel, rue Blaise Pascal, 67000 STRASBOURG, FRANCE ; _publ_contact_author_phone 0390241311 _publ_contact_author_fax 0390241308 _publ_contact_author_email braunst@chimie.u-strasbg.fr _publ_contact_letter ; ; _publ_requested_category FM _publ_section_title ; A new trinitroaromatic compound for stabilized energetic material ; loop_ _publ_author_name _publ_author_address 'Braunstein, Pierre' ; Laboratoire de Chimie de coordination, UMR CNRS 7513 Universite Louis Pasteur Strasbourg France ; 'Siri, Olivier' ; Laboratoire de Chimie de coordination, UMR CNRS 7513 Universite Louis Pasteur Strasbourg France ; _publ_section_references ; Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Polidori, G., Spagna, R. &Viterbo, D. (1989). SIR. J. Appl. Cryst. 22, 389-393. A.L. Spek, PLATON 98, Utrecht University, The Netherland, 1998. KappaCCD Operation Manual (1997), Nonius B.V., Delft, The Nederlands. Otwinowski, Z. & Minor, W. (1997), Methods in Enzymology, 276, 307-326. Sheldrick, G.M. (1997). SHELXL97. Program for the refinement of crystal structures. University of Gottingen. Germany. ; data_wel2 _database_code_depnum_ccdc_archive 'CCDC 226339' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H6 N4 O4' _chemical_formula_sum 'C6 H6 N4 O4' _chemical_formula_weight 198.15 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' 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' H H 0.0000 0.0000 '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' 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 8.7780(10) _cell_length_b 5.6200(10) _cell_length_c 15.635(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.504(5) _cell_angle_gamma 90.00 _cell_volume 762.83(19) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3086 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.725 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _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 ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\p scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5056 _diffrn_reflns_av_R_equivalents 0.0421 _diffrn_reflns_av_sigmaI/netI 0.0617 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 30.01 _reflns_number_total 2215 _reflns_number_gt 1670 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (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. ; _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^)+(0.0554P)^2^+0.1380P] 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 2215 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0733 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1211 _refine_ls_wR_factor_gt 0.1124 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 C6 C 0.37490(16) 0.3345(3) 0.03682(9) 0.0198(3) Uani 1 1 d . . . O2 O 0.11432(13) 0.6220(2) -0.18725(7) 0.0310(3) Uani 1 1 d . . . N3 N 0.07343(14) 0.6539(2) -0.11617(8) 0.0210(3) Uani 1 1 d . . . O1 O -0.04814(12) 0.75273(19) -0.10682(7) 0.0291(3) Uani 1 1 d . . . C5 C 0.26946(15) 0.3805(2) -0.03609(9) 0.0181(3) Uani 1 1 d . . . N4 N 0.24850(14) 0.1969(2) -0.10203(8) 0.0213(3) Uani 1 1 d . . . C1 C 0.39021(16) 0.4847(3) 0.10838(9) 0.0208(3) Uani 1 1 d . . . O4 O 0.11811(13) 0.1646(2) -0.14071(7) 0.0327(3) Uani 1 1 d . . . C2 C 0.29339(16) 0.6884(3) 0.10610(9) 0.0207(3) Uani 1 1 d . . . O3 O 0.36015(13) 0.07405(19) -0.11275(7) 0.0311(3) Uani 1 1 d . . . C4 C 0.17562(15) 0.5818(2) -0.03900(9) 0.0184(3) Uani 1 1 d . . . C3 C 0.18831(16) 0.7319(3) 0.03190(9) 0.0203(3) Uani 1 1 d . . . N1 N 0.49463(17) 0.4347(3) 0.17934(9) 0.0308(3) Uani 1 1 d . . . N2 N 0.29987(18) 0.8329(3) 0.17727(9) 0.0317(3) Uani 1 1 d . . . H1 H 0.551(2) 0.313(4) 0.1753(13) 0.038(6) Uiso 1 1 d . . . H2 H 0.501(2) 0.520(4) 0.2251(15) 0.048(6) Uiso 1 1 d . . . H3 H 0.380(3) 0.839(4) 0.2090(15) 0.046(6) Uiso 1 1 d . . . H4 H 0.241(3) 0.965(4) 0.1736(14) 0.047(6) Uiso 1 1 d . . . H5 H 0.128(2) 0.864(3) 0.0310(11) 0.026(4) Uiso 1 1 d . . . H6 H 0.434(2) 0.194(3) 0.0370(11) 0.031(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 C6 0.0176(6) 0.0208(7) 0.0203(7) 0.0021(5) 0.0004(5) 0.0016(5) O2 0.0392(7) 0.0354(6) 0.0169(5) 0.0010(4) -0.0004(4) 0.0073(5) N3 0.0209(6) 0.0193(6) 0.0211(6) 0.0016(5) -0.0031(5) -0.0005(5) O1 0.0190(5) 0.0332(6) 0.0333(6) 0.0049(5) -0.0026(4) 0.0052(4) C5 0.0187(7) 0.0181(7) 0.0175(6) -0.0001(5) 0.0021(5) -0.0012(5) N4 0.0263(6) 0.0190(6) 0.0173(6) 0.0003(5) -0.0006(5) 0.0001(5) C1 0.0177(6) 0.0262(7) 0.0180(6) 0.0023(6) 0.0009(5) -0.0027(6) O4 0.0306(6) 0.0315(6) 0.0319(6) -0.0082(5) -0.0089(5) -0.0020(5) C2 0.0186(7) 0.0250(7) 0.0181(7) -0.0026(6) 0.0020(5) -0.0022(5) O3 0.0347(6) 0.0273(6) 0.0310(6) -0.0063(5) 0.0042(5) 0.0084(5) C4 0.0159(6) 0.0212(7) 0.0173(6) 0.0013(5) -0.0008(5) 0.0001(5) C3 0.0179(7) 0.0213(7) 0.0215(7) -0.0010(5) 0.0021(5) 0.0024(5) N1 0.0325(8) 0.0341(8) 0.0222(7) -0.0005(6) -0.0082(5) 0.0054(6) N2 0.0301(8) 0.0400(9) 0.0229(7) -0.0116(6) -0.0033(6) 0.0053(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 C6 C5 1.382(2) . ? C6 C1 1.392(2) . ? C6 H6 0.946(19) . ? O2 N3 1.2304(16) . ? N3 O1 1.2307(16) . ? N3 C4 1.4508(17) . ? C5 C4 1.3964(19) . ? C5 N4 1.4507(18) . ? N4 O4 1.2264(16) . ? N4 O3 1.2305(15) . ? C1 N1 1.3599(18) . ? C1 C2 1.423(2) . ? C2 N2 1.3719(19) . ? C2 C3 1.393(2) . ? C4 C3 1.384(2) . ? C3 H5 0.911(18) . ? N1 H1 0.85(2) . ? N1 H2 0.86(2) . ? N2 H3 0.80(2) . ? N2 H4 0.90(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 C5 C6 C1 121.51(13) . . ? C5 C6 H6 117.4(11) . . ? C1 C6 H6 121.1(11) . . ? O2 N3 O1 123.16(12) . . ? O2 N3 C4 118.91(11) . . ? O1 N3 C4 117.88(12) . . ? C6 C5 C4 119.88(13) . . ? C6 C5 N4 116.89(12) . . ? C4 C5 N4 122.74(12) . . ? O4 N4 O3 123.61(12) . . ? O4 N4 C5 117.83(12) . . ? O3 N4 C5 118.43(12) . . ? N1 C1 C6 120.23(14) . . ? N1 C1 C2 120.99(13) . . ? C6 C1 C2 118.77(13) . . ? N2 C2 C3 120.99(14) . . ? N2 C2 C1 120.19(13) . . ? C3 C2 C1 118.77(12) . . ? C3 C4 C5 119.37(13) . . ? C3 C4 N3 117.55(12) . . ? C5 C4 N3 122.87(12) . . ? C4 C3 C2 121.69(13) . . ? C4 C3 H5 120.4(11) . . ? C2 C3 H5 118.0(11) . . ? C1 N1 H1 115.7(14) . . ? C1 N1 H2 121.2(15) . . ? H1 N1 H2 123(2) . . ? C2 N2 H3 117.1(16) . . ? C2 N2 H4 118.8(14) . . ? H3 N2 H4 117(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 C1 C6 C5 C4 0.1(2) . . . . ? C1 C6 C5 N4 -171.99(12) . . . . ? C6 C5 N4 O4 143.02(13) . . . . ? C4 C5 N4 O4 -28.86(19) . . . . ? C6 C5 N4 O3 -33.04(18) . . . . ? C4 C5 N4 O3 155.07(13) . . . . ? C5 C6 C1 N1 179.80(14) . . . . ? C5 C6 C1 C2 0.7(2) . . . . ? N1 C1 C2 N2 -2.6(2) . . . . ? C6 C1 C2 N2 176.51(13) . . . . ? N1 C1 C2 C3 -179.99(13) . . . . ? C6 C1 C2 C3 -0.9(2) . . . . ? C6 C5 C4 C3 -0.7(2) . . . . ? N4 C5 C4 C3 170.91(13) . . . . ? C6 C5 C4 N3 173.76(13) . . . . ? N4 C5 C4 N3 -14.6(2) . . . . ? O2 N3 C4 C3 139.34(14) . . . . ? O1 N3 C4 C3 -37.98(19) . . . . ? O2 N3 C4 C5 -35.25(19) . . . . ? O1 N3 C4 C5 147.43(13) . . . . ? C5 C4 C3 C2 0.5(2) . . . . ? N3 C4 C3 C2 -174.26(12) . . . . ? N2 C2 C3 C4 -177.08(14) . . . . ? C1 C2 C3 C4 0.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.343 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.054