# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shrv89 #TrackingRef 'shrv89-final.cif' _audit_creation_date 2009-10-28 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; guanidinium dinitromethanide ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C1 H6 N3 1+, C1 H1 N2 O4 1-' _chemical_formula_sum 'C2 H7 N5 O4' _chemical_formula_weight 165.13 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 3.497(2) _cell_length_b 17.157(12) _cell_length_c 10.822(7) _cell_angle_alpha 90.00 _cell_angle_beta 92.697(10) _cell_angle_gamma 90.00 _cell_volume 648.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.691 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.157 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.5624 _exptl_absorpt_correction_T_max 0.7454 _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_reflns_number 5579 _diffrn_reflns_av_R_equivalents 0.0582 _diffrn_reflns_av_sigmaI/netI 0.0517 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 26.49 _reflns_number_total 1336 _reflns_number_gt 921 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2 v2009.3-0 (Bruker, 2009)' _computing_cell_refinement 'Bruker APEX2 v2009.3-0 (Bruker, 2009)' _computing_data_reduction ; Bruker SAINT v7.60A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008) ; _computing_structure_solution 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_structure_refinement 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_molecular_graphics 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_publication_material 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _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^)+(0.0887P)^2^+0.0000P] 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 1336 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0842 _refine_ls_R_factor_gt 0.0530 _refine_ls_wR_factor_ref 0.1462 _refine_ls_wR_factor_gt 0.1310 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 -0.0344(7) 0.19512(14) 0.4821(2) 0.0164(5) Uani 1 1 d . . . N2 N -0.0685(6) 0.11906(12) 0.47186(19) 0.0189(5) Uani 1 1 d . . . H2A H 0.0123 0.0887 0.5332 0.023 Uiso 1 1 calc R . . H2B H -0.1722 0.0985 0.4037 0.023 Uiso 1 1 calc R . . N3 N -0.1563(6) 0.24133(12) 0.38871(19) 0.0211(5) Uani 1 1 d . . . H3A H -0.2594 0.2208 0.3205 0.025 Uiso 1 1 calc R . . H3B H -0.1335 0.2922 0.3956 0.025 Uiso 1 1 calc R . . N4 N 0.1220(6) 0.22637(12) 0.58485(18) 0.0196(5) Uani 1 1 d . . . H4A H 0.2030 0.1961 0.6463 0.024 Uiso 1 1 calc R . . H4B H 0.1444 0.2773 0.5914 0.024 Uiso 1 1 calc R . . C5 C 0.3478(7) 0.50389(15) 0.6499(2) 0.0174(6) Uani 1 1 d . . . H5 H 0.2241 0.5309 0.5826 0.021 Uiso 1 1 calc R . . N6 N 0.3508(6) 0.42498(12) 0.64527(17) 0.0167(5) Uani 1 1 d . . . O7 O 0.5055(5) 0.38235(11) 0.72802(15) 0.0225(5) Uani 1 1 d . . . O8 O 0.1840(5) 0.39427(10) 0.55061(15) 0.0223(5) Uani 1 1 d . . . N9 N 0.5102(6) 0.54741(12) 0.74439(17) 0.0165(5) Uani 1 1 d . . . O10 O 0.4717(5) 0.61999(10) 0.73504(16) 0.0229(5) Uani 1 1 d . . . O11 O 0.6913(5) 0.51807(10) 0.83557(16) 0.0217(5) Uani 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 C1 0.0156(13) 0.0230(13) 0.0104(11) 0.0011(10) -0.0017(9) 0.0010(10) N2 0.0256(13) 0.0213(11) 0.0090(9) 0.0011(8) -0.0081(9) 0.0000(9) N3 0.0293(13) 0.0194(11) 0.0139(11) 0.0022(9) -0.0066(10) 0.0000(9) N4 0.0268(12) 0.0205(11) 0.0107(10) 0.0001(8) -0.0085(9) -0.0020(9) C5 0.0181(13) 0.0222(14) 0.0115(12) 0.0007(10) -0.0040(10) 0.0010(10) N6 0.0175(11) 0.0215(12) 0.0107(10) -0.0001(8) -0.0041(8) 0.0005(8) O7 0.0321(11) 0.0241(10) 0.0104(8) 0.0030(7) -0.0096(8) 0.0029(8) O8 0.0302(11) 0.0246(10) 0.0111(8) -0.0025(7) -0.0114(8) -0.0032(7) N9 0.0184(11) 0.0221(13) 0.0086(10) -0.0009(8) -0.0041(8) 0.0001(8) O10 0.0333(11) 0.0175(10) 0.0168(9) -0.0015(7) -0.0107(8) 0.0026(8) O11 0.0288(11) 0.0247(11) 0.0102(8) 0.0013(7) -0.0117(8) 0.0011(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 C1 N2 1.315(3) . ? C1 N4 1.329(3) . ? C1 N3 1.338(3) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? N3 H3A 0.8800 . ? N3 H3B 0.8800 . ? N4 H4A 0.8800 . ? N4 H4B 0.8800 . ? C5 N6 1.355(3) . ? C5 N9 1.368(3) . ? C5 H5 0.9500 . ? N6 O7 1.259(3) . ? N6 O8 1.269(3) . ? N9 O11 1.253(2) . ? N9 O10 1.256(3) . ? 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 N4 120.2(2) . . ? N2 C1 N3 120.0(2) . . ? N4 C1 N3 119.8(2) . . ? C1 N2 H2A 120.0 . . ? C1 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C1 N3 H3A 120.0 . . ? C1 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C1 N4 H4A 120.0 . . ? C1 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? N6 C5 N9 124.7(2) . . ? N6 C5 H5 117.7 . . ? N9 C5 H5 117.7 . . ? O7 N6 O8 119.9(2) . . ? O7 N6 C5 123.9(2) . . ? O8 N6 C5 116.1(2) . . ? O11 N9 O10 120.68(19) . . ? O11 N9 C5 123.1(2) . . ? O10 N9 C5 116.21(19) . . ? 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 N9 C5 N6 O7 -0.2(4) . . . . ? N9 C5 N6 O8 179.6(2) . . . . ? N6 C5 N9 O11 2.4(4) . . . . ? N6 C5 N9 O10 -178.2(2) . . . . ? 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 N2 H2A O11 0.88 2.10 2.971(3) 168.9 2_646 N2 H2B O11 0.88 2.18 2.881(3) 136.6 4_465 N3 H3A O7 0.88 2.18 2.955(3) 147.4 4_465 N3 H3B O10 0.88 2.35 2.921(3) 123.0 3_566 N4 H4A O10 0.88 2.12 2.982(3) 164.6 2_646 N4 H4B O8 0.88 2.06 2.914(3) 163.0 . _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.49 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.341 _refine_diff_density_min -0.365 _refine_diff_density_rms 0.076 _database_code_depnum_ccdc_archive 'CCDC 796443'