# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 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_[1,3-diMe-Im][4-NO2-Im] _database_code_depnum_ccdc_archive 'CCDC 902237' #TrackingRef '14076_web_deposit_cif_file_0_PrestonBeasley_1348091813.Smiglak Azolium Azolates CIF 09-19-12 SK.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H11 N5 O2' _chemical_formula_weight 209.22 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)/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 8.1437(17) _cell_length_b 10.197(2) _cell_length_c 12.090(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.216(4) _cell_angle_gamma 90.00 _cell_volume 1003.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 770 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 26.81 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9845 _exptl_absorpt_correction_T_max 0.9938 _exptl_absorpt_process_details 'SHELX SADABS' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6968 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0391 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 28.27 _reflns_number_total 2381 _reflns_number_gt 1700 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0448P)^2^+0.2783P] 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 2381 _refine_ls_number_parameters 161 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0947 _refine_ls_R_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.1187 _refine_ls_wR_factor_gt 0.1063 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 N8 N 0.3158(2) 0.85558(16) 0.01457(16) 0.0456(4) Uani 1 1 d . . . N10 N 0.25225(18) 0.63811(15) 0.00088(13) 0.0341(4) Uani 1 1 d . . . N13 N 0.42537(18) 0.57955(16) -0.14873(13) 0.0364(4) Uani 1 1 d . . . N3 N 0.18334(18) 0.21151(15) 0.01215(13) 0.0343(4) Uani 1 1 d . . . N1 N 0.10084(17) 0.33381(15) 0.14406(12) 0.0313(4) Uani 1 1 d . . . O1 O 0.37066(19) 0.46617(15) -0.14968(13) 0.0535(4) Uani 1 1 d . . . O2 O 0.53428(16) 0.61436(15) -0.21214(11) 0.0474(4) Uani 1 1 d . . . C9 C 0.2300(2) 0.75139(19) 0.05153(17) 0.0360(5) Uani 1 1 d . . . H9A H 0.161(2) 0.759(2) 0.1136(18) 0.043 Uiso 1 1 d . . . C11 C 0.3623(2) 0.67208(18) -0.07577(15) 0.0312(4) Uani 1 1 d . . . C12 C 0.4003(3) 0.8035(2) -0.06780(18) 0.0411(5) Uani 1 1 d . . . H12A H 0.474(3) 0.853(2) -0.1107(18) 0.049 Uiso 1 1 d . . . C2 C 0.1664(2) 0.33439(19) 0.04530(16) 0.0326(4) Uani 1 1 d . . . H2A H 0.200(2) 0.410(2) 0.0088(16) 0.039 Uiso 1 1 d . . . C5 C 0.0749(2) 0.2061(2) 0.17492(18) 0.0379(5) Uani 1 1 d . . . H5A H 0.024(2) 0.184(2) 0.2419(17) 0.045 Uiso 1 1 d . . . C4 C 0.1267(2) 0.1300(2) 0.09288(18) 0.0397(5) Uani 1 1 d . . . H4A H 0.131(2) 0.038(2) 0.0861(18) 0.048 Uiso 1 1 d . . . C7 C 0.2497(3) 0.1693(2) -0.09270(17) 0.0473(5) Uani 1 1 d . . . H7A H 0.2372 0.0741 -0.1004 0.071 Uiso 0.50 1 calc PR . . H7B H 0.3664 0.1924 -0.0939 0.071 Uiso 0.50 1 calc PR . . H7C H 0.1898 0.2131 -0.1541 0.071 Uiso 0.50 1 calc PR . . H7D H 0.2918 0.2456 -0.1319 0.071 Uiso 0.50 1 calc PR . . H7E H 0.1626 0.1273 -0.1384 0.071 Uiso 0.50 1 calc PR . . H7F H 0.3391 0.1066 -0.0781 0.071 Uiso 0.50 1 calc PR . . C6 C 0.0607(3) 0.4509(2) 0.20708(19) 0.0400(5) Uani 1 1 d . . . H6C H 0.119(3) 0.523(2) 0.179(2) 0.060 Uiso 1 1 d . . . H6B H 0.087(3) 0.438(2) 0.286(2) 0.060 Uiso 1 1 d . . . H6A H -0.055(3) 0.466(2) 0.2003(19) 0.060 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 N8 0.0502(10) 0.0353(9) 0.0516(11) -0.0030(8) 0.0064(9) -0.0005(8) N10 0.0352(8) 0.0345(9) 0.0332(9) -0.0017(7) 0.0095(7) -0.0003(6) N13 0.0313(8) 0.0476(10) 0.0306(9) 0.0009(8) 0.0058(7) 0.0017(7) N3 0.0321(8) 0.0374(9) 0.0336(9) -0.0004(7) 0.0037(7) -0.0007(7) N1 0.0298(8) 0.0350(9) 0.0296(8) 0.0038(7) 0.0060(6) -0.0018(6) O1 0.0606(10) 0.0422(9) 0.0594(10) -0.0152(8) 0.0246(8) -0.0054(7) O2 0.0365(8) 0.0706(10) 0.0363(8) 0.0018(7) 0.0146(6) -0.0005(7) C9 0.0358(10) 0.0390(11) 0.0336(11) -0.0020(9) 0.0055(8) 0.0028(8) C11 0.0298(9) 0.0366(11) 0.0274(9) 0.0019(8) 0.0030(8) 0.0004(8) C12 0.0408(11) 0.0398(12) 0.0428(12) 0.0054(9) 0.0056(9) -0.0053(9) C2 0.0316(9) 0.0357(11) 0.0307(10) 0.0030(9) 0.0032(8) -0.0031(8) C5 0.0391(11) 0.0384(11) 0.0365(11) 0.0070(9) 0.0067(9) -0.0024(8) C4 0.0412(11) 0.0355(11) 0.0424(12) 0.0045(10) 0.0034(9) -0.0026(9) C7 0.0518(13) 0.0559(13) 0.0344(11) -0.0085(10) 0.0056(10) 0.0037(10) C6 0.0452(12) 0.0390(12) 0.0365(11) -0.0016(9) 0.0104(10) 0.0002(9) _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 N8 C12 1.342(3) . ? N8 C9 1.357(3) . ? N10 C9 1.323(2) . ? N10 C11 1.359(2) . ? N13 O1 1.239(2) . ? N13 O2 1.2461(19) . ? N13 C11 1.402(2) . ? N3 C2 1.324(2) . ? N3 C4 1.375(3) . ? N3 C7 1.462(2) . ? N1 C2 1.327(2) . ? N1 C5 1.374(2) . ? N1 C6 1.460(3) . ? C11 C12 1.378(3) . ? C5 C4 1.340(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 C12 N8 C9 102.72(17) . . ? C9 N10 C11 101.47(16) . . ? O1 N13 O2 121.63(16) . . ? O1 N13 C11 119.57(15) . . ? O2 N13 C11 118.80(16) . . ? C2 N3 C4 108.39(16) . . ? C2 N3 C7 125.97(17) . . ? C4 N3 C7 125.64(18) . . ? C2 N1 C5 108.67(16) . . ? C2 N1 C6 124.87(16) . . ? C5 N1 C6 126.44(16) . . ? N10 C9 N8 116.71(18) . . ? N10 C11 C12 110.64(17) . . ? N10 C11 N13 121.64(16) . . ? C12 C11 N13 127.71(17) . . ? N8 C12 C11 108.45(18) . . ? N3 C2 N1 108.56(17) . . ? C4 C5 N1 106.97(17) . . ? C5 C4 N3 107.40(18) . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.204 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.044 data_[1,3-diMe-Im][2-Me-5-NO2-Im] _database_code_depnum_ccdc_archive 'CCDC 902238' #TrackingRef '14076_web_deposit_cif_file_0_PrestonBeasley_1348091813.Smiglak Azolium Azolates CIF 09-19-12 SK.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H26 N10 O4' _chemical_formula_weight 446.49 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 6.9280(13) _cell_length_b 8.2326(15) _cell_length_c 10.864(2) _cell_angle_alpha 74.659(3) _cell_angle_beta 74.897(3) _cell_angle_gamma 68.180(3) _cell_volume 545.57(17) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1456 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 27.32 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 236 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9801 _exptl_absorpt_correction_T_max 0.9970 _exptl_absorpt_process_details 'SHELX SADABS' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 3708 _diffrn_reflns_av_R_equivalents 0.0191 _diffrn_reflns_av_sigmaI/netI 0.0402 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 28.19 _reflns_number_total 2473 _reflns_number_gt 1836 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0608P)^2^+0.1266P] 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 2473 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0749 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1289 _refine_ls_wR_factor_gt 0.1204 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.001 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 O1 O 0.2348(2) 0.34496(18) 0.22391(14) 0.0403(4) Uani 1 1 d . . . O2 O 0.1963(2) 0.20761(19) 0.09070(13) 0.0384(4) Uani 1 1 d . . . N1 N 0.2565(2) -0.0662(2) 0.84895(14) 0.0260(3) Uani 1 1 d . . . N3 N 0.2812(2) -0.3369(2) 0.85903(14) 0.0260(3) Uani 1 1 d . . . N8 N 0.2834(3) -0.1269(2) 0.48256(15) 0.0331(4) Uani 1 1 d . . . N10 N 0.2046(2) -0.0892(2) 0.28330(14) 0.0277(4) Uani 1 1 d . . . N13 N 0.2206(2) 0.2101(2) 0.19971(15) 0.0293(4) Uani 1 1 d . . . C2 C 0.2722(3) -0.1830(2) 0.78004(17) 0.0255(4) Uani 1 1 d . . . H2A H 0.2762 -0.1597 0.6891 0.031 Uiso 1 1 calc R . . C4 C 0.2700(3) -0.3190(3) 0.98333(18) 0.0285(4) Uani 1 1 d . . . H4A H 0.2725 -0.4092 1.0590 0.034 Uiso 1 1 calc R . . C5 C 0.2548(3) -0.1492(2) 0.97714(17) 0.0284(4) Uani 1 1 d . . . H5A H 0.2449 -0.0968 1.0476 0.034 Uiso 1 1 calc R . . C6 C 0.2375(3) 0.1203(2) 0.7970(2) 0.0354(5) Uani 1 1 d . . . H6A H 0.188(8) 0.1862(17) 0.8685(11) 0.053 Uiso 0.50 1 calc PR A 1 H6B H 0.136(7) 0.171(2) 0.738(4) 0.053 Uiso 0.50 1 calc PR A 1 H6C H 0.376(3) 0.1292(6) 0.750(5) 0.053 Uiso 0.50 1 calc PR A 1 H6D H 0.279(8) 0.1381(15) 0.7023(14) 0.053 Uiso 0.50 1 d PR A 2 H6E H 0.330(7) 0.153(2) 0.833(4) 0.053 Uiso 0.50 1 d PR A 2 H6F H 0.091(3) 0.1949(12) 0.821(4) 0.053 Uiso 0.50 1 d PR A 2 C7 C 0.2962(4) -0.4990(3) 0.8212(2) 0.0368(5) Uani 1 1 d . . . H7C H 0.266(4) -0.469(3) 0.743(3) 0.055 Uiso 1 1 d . . . H7B H 0.440(4) -0.582(3) 0.818(2) 0.055 Uiso 1 1 d . . . H7A H 0.198(4) -0.547(3) 0.872(2) 0.055 Uiso 1 1 d . . . C9 C 0.2340(3) -0.1956(2) 0.39709(18) 0.0296(4) Uani 1 1 d . . . C11 C 0.2326(3) 0.0602(2) 0.29794(17) 0.0261(4) Uani 1 1 d . . . C12 C 0.2804(3) 0.0362(3) 0.41877(18) 0.0302(4) Uani 1 1 d . . . H12A H 0.3065 0.1214 0.4508 0.036 Uiso 1 1 calc R . . C13 C 0.2088(4) -0.3756(3) 0.4336(2) 0.0415(5) Uani 1 1 d . . . H13A H 0.182(2) -0.4038(10) 0.3600(11) 0.062 Uiso 1 1 calc R . . H13B H 0.091(2) -0.3760(6) 0.5047(14) 0.062 Uiso 1 1 calc R . . H13C H 0.336(2) -0.4635(13) 0.4599(15) 0.062 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 O1 0.0526(9) 0.0328(8) 0.0416(9) -0.0056(7) -0.0110(7) -0.0198(7) O2 0.0474(9) 0.0494(9) 0.0222(7) -0.0007(6) -0.0111(6) -0.0210(7) N1 0.0282(8) 0.0278(8) 0.0238(8) -0.0045(6) -0.0039(6) -0.0118(6) N3 0.0284(8) 0.0267(8) 0.0237(8) -0.0056(6) -0.0035(6) -0.0100(6) N8 0.0407(10) 0.0401(10) 0.0228(8) -0.0048(7) -0.0076(7) -0.0174(7) N10 0.0304(8) 0.0339(9) 0.0220(8) -0.0052(7) -0.0044(6) -0.0143(6) N13 0.0268(8) 0.0355(9) 0.0265(8) -0.0046(7) -0.0046(6) -0.0122(6) C2 0.0273(9) 0.0304(10) 0.0208(9) -0.0053(7) -0.0035(7) -0.0117(7) C4 0.0283(9) 0.0339(10) 0.0206(9) -0.0027(7) -0.0044(7) -0.0089(7) C5 0.0290(9) 0.0363(11) 0.0222(9) -0.0089(8) -0.0048(7) -0.0107(8) C6 0.0415(11) 0.0274(10) 0.0389(12) -0.0054(9) -0.0040(9) -0.0158(8) C7 0.0485(13) 0.0290(11) 0.0379(12) -0.0108(9) -0.0068(10) -0.0159(9) C9 0.0311(10) 0.0335(10) 0.0253(10) -0.0051(8) -0.0037(7) -0.0130(8) C11 0.0278(9) 0.0314(10) 0.0210(9) -0.0051(7) -0.0032(7) -0.0123(7) C12 0.0377(11) 0.0338(11) 0.0233(10) -0.0062(8) -0.0059(8) -0.0155(8) C13 0.0522(13) 0.0382(12) 0.0381(12) -0.0028(9) -0.0098(10) -0.0211(10) _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 O1 N13 1.249(2) . ? O2 N13 1.246(2) . ? N1 C2 1.326(2) . ? N1 C5 1.379(2) . ? N1 C6 1.457(2) . ? N3 C2 1.319(2) . ? N3 C4 1.376(2) . ? N3 C7 1.458(2) . ? N8 C12 1.334(3) . ? N8 C9 1.373(2) . ? N10 C9 1.328(2) . ? N10 C11 1.368(2) . ? N13 C11 1.394(2) . ? C4 C5 1.347(3) . ? C9 C13 1.493(3) . ? C11 C12 1.383(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 C2 N1 C5 108.75(15) . . ? C2 N1 C6 125.08(16) . . ? C5 N1 C6 126.15(15) . . ? C2 N3 C4 109.07(15) . . ? C2 N3 C7 125.50(16) . . ? C4 N3 C7 125.41(16) . . ? C12 N8 C9 103.73(15) . . ? C9 N10 C11 101.91(14) . . ? O2 N13 O1 121.49(16) . . ? O2 N13 C11 119.96(15) . . ? O1 N13 C11 118.55(15) . . ? N3 C2 N1 108.46(16) . . ? C5 C4 N3 106.88(16) . . ? C4 C5 N1 106.84(16) . . ? N10 C9 N8 115.43(16) . . ? N10 C9 C13 123.22(17) . . ? N8 C9 C13 121.32(17) . . ? N10 C11 C12 110.63(16) . . ? N10 C11 N13 122.72(15) . . ? C12 C11 N13 126.62(16) . . ? N8 C12 C11 108.29(16) . . ? _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 28.19 _diffrn_measured_fraction_theta_full 0.919 _refine_diff_density_max 0.231 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.047 data_[1,3-diMe-Im][4,5-diNO2-Im] _database_code_depnum_ccdc_archive 'CCDC 902239' #TrackingRef '14076_web_deposit_cif_file_0_PrestonBeasley_1348091813.Smiglak Azolium Azolates CIF 09-19-12 SK.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 N6 O4' _chemical_formula_weight 254.22 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 7.8099(17) _cell_length_b 12.914(3) _cell_length_c 11.053(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.967(4) _cell_angle_gamma 90.00 _cell_volume 1104.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 986 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 26.80 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.529 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9754 _exptl_absorpt_correction_T_max 0.9938 _exptl_absorpt_process_details 'SHELX SADABS' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7737 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_sigmaI/netI 0.0337 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 28.31 _reflns_number_total 2644 _reflns_number_gt 1986 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0684P)^2^+0.2422P] 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 refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2644 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0769 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1318 _refine_ls_wR_factor_gt 0.1210 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 O1 O 0.34216(19) 0.07847(13) 0.96313(13) 0.0495(4) Uani 1 1 d . . . O2 O 0.50067(17) 0.15087(12) 1.11557(13) 0.0435(4) Uani 1 1 d . . . O3 O 0.4800(2) 0.07232(13) 1.34775(14) 0.0522(4) Uani 1 1 d . . . O4 O 0.3428(2) 0.18269(15) 1.44254(14) 0.0626(5) Uani 1 1 d . . . N1 N 0.03988(19) 0.11163(11) 0.67632(13) 0.0289(3) Uani 1 1 d . . . N3 N -0.20118(19) 0.13978(11) 0.74371(13) 0.0271(3) Uani 1 1 d . . . N8 N 0.0492(2) 0.13110(11) 1.27871(14) 0.0305(4) Uani 1 1 d . . . N10 N 0.05536(19) 0.11563(11) 1.07355(14) 0.0297(4) Uani 1 1 d . . . N13 N 0.3629(2) 0.11502(12) 1.06664(14) 0.0321(4) Uani 1 1 d . . . N14 N 0.3545(2) 0.12674(12) 1.35546(14) 0.0340(4) Uani 1 1 d . . . C2 C -0.0347(2) 0.12167(13) 0.77629(17) 0.0267(4) Uani 1 1 d . . . H2A H 0.020(3) 0.1161(15) 0.857(2) 0.032 Uiso 1 1 d . . . C4 C -0.2344(3) 0.14162(14) 0.61780(17) 0.0323(4) Uani 1 1 d . . . H4A H -0.344(3) 0.1547(16) 0.580(2) 0.039 Uiso 1 1 d . . . C5 C -0.0839(3) 0.12429(14) 0.57615(18) 0.0329(4) Uani 1 1 d . . . H5A H -0.060(3) 0.1220(15) 0.499(2) 0.040 Uiso 1 1 d . . . C6 C 0.2221(3) 0.0867(2) 0.6741(3) 0.0429(5) Uani 1 1 d . . . H6A H 0.235(7) 0.057(5) 0.598(5) 0.064 Uiso 0.50 1 d P . . H6B H 0.270(8) 0.039(4) 0.745(6) 0.064 Uiso 0.50 1 d P . . H6C H 0.299(9) 0.150(6) 0.685(5) 0.064 Uiso 0.50 1 d P . . H6D H 0.298(8) 0.089(5) 0.762(6) 0.064 Uiso 0.50 1 d P . . H6E H 0.273(9) 0.146(6) 0.636(5) 0.064 Uiso 0.50 1 d P . . H6F H 0.240(7) 0.020(5) 0.657(6) 0.064 Uiso 0.50 1 d P . . C7 C -0.3253(3) 0.1570(2) 0.8288(2) 0.0428(5) Uani 1 1 d . . . H7A H -0.265(4) 0.151(2) 0.908(3) 0.064 Uiso 1 1 d . . . H7B H -0.415(4) 0.111(2) 0.813(3) 0.064 Uiso 1 1 d . . . H7C H -0.372(3) 0.229(2) 0.819(2) 0.064 Uiso 1 1 d . . . C9 C -0.0392(2) 0.12392(14) 1.16521(18) 0.0319(4) Uani 1 1 d . . . H9A H -0.1620 0.1247 1.1511 0.038 Uiso 1 1 calc R . . C11 C 0.2179(2) 0.11647(13) 1.13216(15) 0.0253(4) Uani 1 1 d . . . C12 C 0.2137(2) 0.12665(12) 1.25655(16) 0.0259(4) 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 O1 0.0458(9) 0.0743(11) 0.0312(8) -0.0154(7) 0.0149(7) -0.0046(8) O2 0.0269(7) 0.0599(9) 0.0437(9) -0.0036(7) 0.0049(6) -0.0076(6) O3 0.0399(9) 0.0645(10) 0.0475(10) 0.0017(7) -0.0102(7) 0.0095(7) O4 0.0690(12) 0.0838(13) 0.0344(9) -0.0259(8) 0.0051(8) -0.0145(9) N1 0.0291(8) 0.0312(8) 0.0269(8) 0.0003(6) 0.0059(6) -0.0002(6) N3 0.0263(8) 0.0298(7) 0.0253(8) -0.0002(6) 0.0034(6) 0.0005(6) N8 0.0310(8) 0.0296(8) 0.0325(9) 0.0005(6) 0.0101(7) 0.0019(6) N10 0.0274(8) 0.0319(8) 0.0292(8) 0.0026(6) 0.0022(6) -0.0009(6) N13 0.0291(8) 0.0403(9) 0.0278(8) -0.0007(6) 0.0070(6) -0.0011(6) N14 0.0382(9) 0.0406(9) 0.0227(8) 0.0001(6) 0.0027(7) -0.0107(7) C2 0.0284(9) 0.0276(8) 0.0238(9) 0.0010(7) 0.0026(7) -0.0008(7) C4 0.0328(10) 0.0355(10) 0.0266(10) 0.0022(7) -0.0026(8) -0.0001(7) C5 0.0418(11) 0.0339(9) 0.0227(9) 0.0005(7) 0.0031(8) -0.0002(8) C6 0.0280(11) 0.0556(14) 0.0473(14) 0.0011(11) 0.0134(10) 0.0038(10) C7 0.0343(11) 0.0575(14) 0.0389(12) 0.0021(10) 0.0132(9) 0.0078(10) C9 0.0249(9) 0.0321(9) 0.0393(11) 0.0052(8) 0.0065(8) 0.0030(7) C11 0.0263(9) 0.0251(8) 0.0249(9) 0.0002(6) 0.0052(7) 0.0003(6) C12 0.0301(9) 0.0245(8) 0.0233(9) 0.0004(6) 0.0046(7) -0.0006(7) _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 O1 N13 1.227(2) . ? O2 N13 1.2262(19) . ? O3 N14 1.219(2) . ? O4 N14 1.217(2) . ? N1 C2 1.325(2) . ? N1 C5 1.375(2) . ? N1 C6 1.462(3) . ? N3 C2 1.321(2) . ? N3 C4 1.380(2) . ? N3 C7 1.458(3) . ? N8 C12 1.342(2) . ? N8 C9 1.349(3) . ? N10 C9 1.338(2) . ? N10 C11 1.343(2) . ? N13 C11 1.426(2) . ? N14 C12 1.439(2) . ? C4 C5 1.339(3) . ? C11 C12 1.386(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 C2 N1 C5 108.57(16) . . ? C2 N1 C6 125.24(17) . . ? C5 N1 C6 126.14(17) . . ? C2 N3 C4 108.58(16) . . ? C2 N3 C7 124.61(16) . . ? C4 N3 C7 126.80(16) . . ? C12 N8 C9 101.93(15) . . ? C9 N10 C11 102.60(15) . . ? O2 N13 O1 123.41(16) . . ? O2 N13 C11 118.75(15) . . ? O1 N13 C11 117.84(15) . . ? O4 N14 O3 123.14(18) . . ? O4 N14 C12 117.93(18) . . ? O3 N14 C12 118.93(16) . . ? N3 C2 N1 108.66(16) . . ? C5 C4 N3 106.99(17) . . ? C4 C5 N1 107.21(17) . . ? N10 C9 N8 116.41(16) . . ? N10 C11 C12 109.17(16) . . ? N10 C11 N13 121.25(15) . . ? C12 C11 N13 129.40(16) . . ? N8 C12 C11 109.89(15) . . ? N8 C12 N14 120.75(16) . . ? C11 C12 N14 129.25(17) . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.231 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.043 data_[1,3-diMe-Im][4-NO2-1,2,3-Tri] _database_code_depnum_ccdc_archive 'CCDC 902240' #TrackingRef '14076_web_deposit_cif_file_0_PrestonBeasley_1348091813.Smiglak Azolium Azolates CIF 09-19-12 SK.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H10 N6 O2' _chemical_formula_weight 210.21 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 Cmca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z+1/2' '-x, y+1/2, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1, z+1/2' '-x+1/2, y+1, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x, y-1/2, -z-1/2' 'x, -y-1/2, z-1/2' '-x, y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, y, -z-1/2' 'x+1/2, -y, z-1/2' '-x+1/2, y+1/2, z' _cell_length_a 6.4782(6) _cell_length_b 26.704(2) _cell_length_c 11.0823(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1917.2(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3463 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 28.25 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.457 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9585 _exptl_absorpt_correction_T_max 0.9966 _exptl_absorpt_process_details 'SHELX SADABS' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6450 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 28.25 _reflns_number_total 1279 _reflns_number_gt 1108 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0527P)^2^+1.2692P] 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 0.0016(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1279 _refine_ls_number_parameters 106 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1085 _refine_ls_wR_factor_gt 0.1035 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 O1 O 0.0000 -0.54861(5) 0.69149(12) 0.0544(5) Uani 1 2 d S . . O2 O 0.0000 -0.50716(5) 0.85825(15) 0.0855(8) Uani 1 2 d S . . N1 N 0.0000 -0.69202(5) 0.50958(12) 0.0245(3) Uani 1 2 d S . . N3 N 0.0000 -0.62279(5) 0.40989(13) 0.0287(3) Uani 1 2 d S . . N8 N 0.0000 -0.64667(6) 1.01541(14) 0.0308(4) Uani 1 2 d S . . N9 N 0.0000 -0.66998(5) 0.90556(14) 0.0310(4) Uani 1 2 d S . . N10 N 0.0000 -0.63688(5) 0.81649(14) 0.0311(4) Uani 1 2 d S . . N13 N 0.0000 -0.54673(6) 0.80229(15) 0.0461(5) Uani 1 2 d S . . C2 C 0.0000 -0.64255(6) 0.52010(15) 0.0263(4) Uani 1 2 d S . . H2A H 0.0000 -0.6258(8) 0.594(2) 0.039(6) Uiso 1 2 d S . . C4 C 0.0000 -0.66105(7) 0.32643(17) 0.0319(4) Uani 1 2 d S . . H4A H 0.0000 -0.6547(8) 0.242(2) 0.045(6) Uiso 1 2 d S . . C5 C 0.0000 -0.70438(7) 0.38911(16) 0.0296(4) Uani 1 2 d S . . H5AA H 0.0000 -0.7396(9) 0.365(2) 0.043(6) Uiso 1 2 d S . . C6 C 0.0000 -0.72718(6) 0.61075(16) 0.0303(4) Uani 1 2 d S . . H6A H -0.0479 -0.7600 0.5829 0.045 Uiso 0.50 1 calc PR . . H6B H -0.0924 -0.7148 0.6741 0.045 Uiso 0.50 1 calc PR . . H6C H 0.1403 -0.7303 0.6430 0.045 Uiso 0.50 1 calc PR . . C7 C 0.0000 -0.56895(7) 0.3835(2) 0.0419(5) Uani 1 2 d S . . H7A H -0.0587 -0.5507 0.4520 0.063 Uiso 0.50 1 calc PR . . H7B H -0.0832 -0.5626 0.3112 0.063 Uiso 0.50 1 calc PR . . H7C H 0.1419 -0.5576 0.3695 0.063 Uiso 0.50 1 calc PR . . C11 C 0.0000 -0.59192(6) 0.87036(16) 0.0300(4) Uani 1 2 d S . . C12 C 0.0000 -0.59758(6) 0.99353(16) 0.0311(4) Uani 1 2 d S . . H12A H 0.0000 -0.5733(8) 1.056(2) 0.037(6) Uiso 1 2 d S . . 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 O1 0.1122(15) 0.0273(7) 0.0238(7) 0.0027(5) 0.000 0.000 O2 0.202(3) 0.0185(7) 0.0358(9) -0.0051(6) 0.000 0.000 N1 0.0310(7) 0.0214(6) 0.0211(7) -0.0008(5) 0.000 0.000 N3 0.0341(8) 0.0266(7) 0.0253(7) 0.0039(5) 0.000 0.000 N8 0.0358(8) 0.0288(7) 0.0277(8) 0.0028(6) 0.000 0.000 N9 0.0391(8) 0.0224(7) 0.0314(8) 0.0009(5) 0.000 0.000 N10 0.0467(9) 0.0191(6) 0.0274(8) -0.0009(5) 0.000 0.000 N13 0.0925(15) 0.0190(7) 0.0268(8) -0.0017(6) 0.000 0.000 C2 0.0339(9) 0.0224(7) 0.0224(8) 0.0001(6) 0.000 0.000 C4 0.0367(10) 0.0388(9) 0.0203(8) -0.0003(7) 0.000 0.000 C5 0.0349(9) 0.0299(8) 0.0240(8) -0.0049(6) 0.000 0.000 C6 0.0416(10) 0.0223(7) 0.0269(9) 0.0043(6) 0.000 0.000 C7 0.0555(13) 0.0275(9) 0.0426(11) 0.0145(8) 0.000 0.000 C11 0.0453(10) 0.0195(7) 0.0254(8) -0.0019(6) 0.000 0.000 C12 0.0419(10) 0.0263(8) 0.0252(9) -0.0023(6) 0.000 0.000 _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 O1 N13 1.229(2) . ? O2 N13 1.225(2) . ? N1 C2 1.326(2) . ? N1 C5 1.375(2) . ? N1 C6 1.462(2) . ? N3 C2 1.330(2) . ? N3 C4 1.378(2) . ? N3 C7 1.467(2) . ? N8 C12 1.333(2) . ? N8 N9 1.367(2) . ? N9 N10 1.325(2) . ? N10 C11 1.341(2) . ? N13 C11 1.423(2) . ? C4 C5 1.350(3) . ? C11 C12 1.373(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 C2 N1 C5 108.92(14) . . ? C2 N1 C6 124.91(14) . . ? C5 N1 C6 126.17(14) . . ? C2 N3 C4 108.78(14) . . ? C2 N3 C7 124.89(16) . . ? C4 N3 C7 126.33(16) . . ? C12 N8 N9 106.60(14) . . ? N10 N9 N8 111.07(13) . . ? N9 N10 C11 105.41(14) . . ? O2 N13 O1 122.75(17) . . ? O2 N13 C11 117.58(16) . . ? O1 N13 C11 119.67(16) . . ? N1 C2 N3 108.33(14) . . ? C5 C4 N3 106.87(16) . . ? C4 C5 N1 107.09(15) . . ? N10 C11 C12 110.11(15) . . ? N10 C11 N13 121.56(16) . . ? C12 C11 N13 128.33(16) . . ? N8 C12 C11 106.80(16) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.278 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.038