# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'RSC Advances' _journal_coden_cambridge 1500 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Alan R. Katritzky' _publ_contact_author_email katritzky@chem.ufl.edu loop_ _publ_author_name J.-C.M.Monbaliu L.K.Beagle J.Kovacs M.Zeller C.V.Stevens ; A.R.Katritzky ; data_mo_20140402_0m _database_code_depnum_ccdc_archive 'CCDC 883509' #TrackingRef '- Compound 4c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '0.937(C12 H14 N4 O), 0.063(C12 H14 N4 O2)' _chemical_formula_sum 'C12 H14 N4 O1.063' _chemical_formula_weight 231.28 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 11.7352(5) _cell_length_b 8.5659(3) _cell_length_c 12.1021(4) _cell_angle_alpha 90.00 _cell_angle_beta 110.616(2) _cell_angle_gamma 90.00 _cell_volume 1138.63(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6067 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 30.60 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 490.4 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6840 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_process_details 'Apex2 v2011.2-0 (Bruker, 2011)' _exptl_special_details ; We would like to thank Matthew Panzner of the University of Akron for collection of single crystal frame data. We acknowledge the National Science Foundation (CHE-0840446) for funds used to purchase the Bruker ApexII Duo CCD X-ray diffractometer used in this research. The nitrone unit is partially oxidized to a nitro group with an occupancy ratio of 0.937(2) to 0.063(2). The O and N atoms of the minor moiety were constrained to have the same ADPs as their major moiety counterparts, and the C-N distances in the minor moiety were restrained to be similar top those in the major moiety. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'ImuS micro--focus source with QUAZAR optics' _diffrn_radiation_monochromator 'Quasar mirror monochromator' _diffrn_measurement_device_type 'Bruker AXS APEX DUO CCD diffractometer' _diffrn_measurement_method '\w and \p scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns.reduction_process narrow--frame _diffrn_reflns_number 14435 _diffrn_reflns_av_R_equivalents 0.0226 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 30.62 _reflns_number_total 3407 _reflns_number_gt 2873 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 v2011.2-0 (Bruker, 2011)' _computing_cell_refinement 'Apex2 v2011.2-0' _computing_data_reduction 'Apex2 v2011.2-0' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2003; Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0455P)^2^+0.4432P] 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 3407 _refine_ls_number_parameters 164 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.1041 _refine_ls_wR_factor_gt 0.0976 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 C1 C 0.77567(9) -0.10940(11) 0.14620(8) 0.01378(18) Uani 1 1 d . A . C2 C 0.79170(10) -0.21211(12) 0.24239(9) 0.0173(2) Uani 1 1 d . . . H2 H 0.7344 -0.2173 0.2815 0.021 Uiso 1 1 calc R . . C3 C 0.89408(10) -0.30345(13) 0.27611(9) 0.0203(2) Uani 1 1 d . . . H3 H 0.9079 -0.3737 0.3403 0.024 Uiso 1 1 calc R . . C4 C 0.98056(10) -0.29652(13) 0.21796(10) 0.0214(2) Uani 1 1 d . . . H4 H 1.0503 -0.3619 0.2450 0.026 Uiso 1 1 calc R . . C5 C 0.96646(9) -0.19876(12) 0.12438(9) 0.0185(2) Uani 1 1 d . . . H5 H 1.0243 -0.1950 0.0858 0.022 Uiso 1 1 calc R . . C6 C 0.86122(9) -0.10387(11) 0.08839(8) 0.01371(18) Uani 1 1 d . A . C7 C 0.64136(9) 0.16085(11) -0.07875(8) 0.01383(18) Uani 1 1 d D . . C8 C 0.56363(9) 0.26087(12) -0.02825(9) 0.01595(19) Uani 1 1 d . A . H8A H 0.4973 0.3105 -0.0936 0.019 Uiso 1 1 calc R . . H8B H 0.5263 0.1938 0.0163 0.019 Uiso 1 1 calc R . . C9 C 0.64082(10) 0.38689(12) 0.05335(9) 0.0180(2) Uani 1 1 d . . . H9A H 0.5880 0.4532 0.0822 0.022 Uiso 1 1 calc R A . H9B H 0.7022 0.3369 0.1226 0.022 Uiso 1 1 calc R . . C10 C 0.70532(10) 0.48886(12) -0.00985(10) 0.0200(2) Uani 1 1 d . A . H10A H 0.7556 0.5682 0.0454 0.024 Uiso 1 1 calc R . . H10B H 0.6443 0.5439 -0.0766 0.024 Uiso 1 1 calc R . . C11 C 0.78618(9) 0.38774(12) -0.05585(9) 0.0176(2) Uani 1 1 d . . . H11A H 0.8509 0.3391 0.0116 0.021 Uiso 1 1 calc R A . H11B H 0.8257 0.4540 -0.0990 0.021 Uiso 1 1 calc R . . C12 C 0.71149(9) 0.26027(12) -0.13809(8) 0.01510(19) Uani 1 1 d . A . H12A H 0.6533 0.3092 -0.2099 0.018 Uiso 1 1 calc R . . H12B H 0.7666 0.1923 -0.1626 0.018 Uiso 1 1 calc R . . N1 N 0.68601(8) -0.00531(9) 0.09413(7) 0.01457(17) Uani 1 1 d . . . N2 N 0.72175(7) 0.05757(9) 0.01071(7) 0.01280(16) Uani 1 1 d . A . N3 N 0.82457(8) 0.00343(10) 0.00114(7) 0.01385(17) Uani 1 1 d . . . N4 N 0.5531(2) 0.06439(18) -0.17882(19) 0.0193(4) Uani 0.937(2) 1 d PD A 1 O1 O 0.57028(14) -0.07450(18) -0.17046(12) 0.0229(3) Uani 0.937(2) 1 d P A 1 N4B N 0.561(4) 0.041(4) -0.168(4) 0.0193(4) Uani 0.063(2) 1 d PD A 2 O1B O 0.4827(12) 0.1029(15) -0.2428(12) 0.0229(3) Uani 0.063(2) 1 d P A 2 O2B O 0.589(3) -0.093(4) -0.147(2) 0.0229(3) Uani 0.063(2) 1 d P A 2 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 0.0148(4) 0.0120(4) 0.0153(4) -0.0016(3) 0.0063(3) -0.0013(3) C2 0.0216(5) 0.0158(4) 0.0165(4) 0.0005(3) 0.0093(4) -0.0012(4) C3 0.0253(5) 0.0185(5) 0.0169(4) 0.0044(4) 0.0071(4) 0.0018(4) C4 0.0198(5) 0.0215(5) 0.0220(5) 0.0054(4) 0.0062(4) 0.0059(4) C5 0.0154(4) 0.0202(5) 0.0209(5) 0.0037(4) 0.0077(4) 0.0042(4) C6 0.0134(4) 0.0130(4) 0.0148(4) -0.0005(3) 0.0051(3) -0.0003(3) C7 0.0126(4) 0.0134(4) 0.0142(4) -0.0008(3) 0.0031(3) 0.0013(3) C8 0.0145(4) 0.0151(4) 0.0197(4) 0.0009(3) 0.0078(4) 0.0028(3) C9 0.0219(5) 0.0166(4) 0.0165(4) -0.0012(3) 0.0081(4) 0.0036(4) C10 0.0235(5) 0.0142(4) 0.0226(5) -0.0021(4) 0.0085(4) -0.0010(4) C11 0.0175(5) 0.0161(4) 0.0202(5) 0.0016(4) 0.0077(4) -0.0008(4) C12 0.0157(4) 0.0167(4) 0.0139(4) 0.0017(3) 0.0065(3) 0.0019(3) N1 0.0157(4) 0.0135(4) 0.0163(4) 0.0003(3) 0.0080(3) 0.0000(3) N2 0.0123(4) 0.0123(3) 0.0147(4) 0.0000(3) 0.0060(3) 0.0008(3) N3 0.0119(4) 0.0143(4) 0.0163(4) 0.0008(3) 0.0060(3) 0.0016(3) N4 0.0163(7) 0.0199(8) 0.0199(7) -0.0039(6) 0.0041(5) -0.0016(7) O1 0.0219(7) 0.0183(6) 0.0260(7) -0.0061(5) 0.0055(5) -0.0021(4) N4B 0.0163(7) 0.0199(8) 0.0199(7) -0.0039(6) 0.0041(5) -0.0016(7) O1B 0.0219(7) 0.0183(6) 0.0260(7) -0.0061(5) 0.0055(5) -0.0021(4) O2B 0.0219(7) 0.0183(6) 0.0260(7) -0.0061(5) 0.0055(5) -0.0021(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 N1 1.3536(12) . ? C1 C6 1.4121(13) . ? C1 C2 1.4179(13) . ? C2 C3 1.3700(15) . ? C2 H2 0.9500 . ? C3 C4 1.4254(16) . ? C3 H3 0.9500 . ? C4 C5 1.3709(14) . ? C4 H4 0.9500 . ? C5 C6 1.4131(14) . ? C5 H5 0.9500 . ? C6 N3 1.3510(12) . ? C7 N2 1.4580(12) . ? C7 C8 1.5272(13) . ? C7 C12 1.5279(14) . ? C7 N4 1.5295(17) . ? C7 N4B 1.544(19) . ? C8 C9 1.5267(14) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.5260(15) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.5272(15) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.5286(14) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? N1 N2 1.3354(12) . ? N2 N3 1.3352(11) . ? N4 O1 1.205(2) . ? N4B O1B 1.17(4) . ? N4B O2B 1.19(5) . ? 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 N1 C1 C6 108.60(8) . . ? N1 C1 C2 130.36(9) . . ? C6 C1 C2 121.03(9) . . ? C3 C2 C1 116.61(10) . . ? C3 C2 H2 121.7 . . ? C1 C2 H2 121.7 . . ? C2 C3 C4 122.09(10) . . ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? C5 C4 C3 122.25(10) . . ? C5 C4 H4 118.9 . . ? C3 C4 H4 118.9 . . ? C4 C5 C6 116.36(10) . . ? C4 C5 H5 121.8 . . ? C6 C5 H5 121.8 . . ? N3 C6 C1 108.90(8) . . ? N3 C6 C5 129.45(9) . . ? C1 C6 C5 121.65(9) . . ? N2 C7 C8 111.39(8) . . ? N2 C7 C12 111.87(8) . . ? C8 C7 C12 111.83(8) . . ? N2 C7 N4 109.94(9) . . ? C8 C7 N4 106.64(14) . . ? C12 C7 N4 104.82(13) . . ? N2 C7 N4B 100.9(16) . . ? C8 C7 N4B 111(2) . . ? C12 C7 N4B 110(2) . . ? C9 C8 C7 110.71(8) . . ? C9 C8 H8A 109.5 . . ? C7 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C10 C9 C8 111.51(8) . . ? C10 C9 H9A 109.3 . . ? C8 C9 H9A 109.3 . . ? C10 C9 H9B 109.3 . . ? C8 C9 H9B 109.3 . . ? H9A C9 H9B 108.0 . . ? C9 C10 C11 109.85(8) . . ? C9 C10 H10A 109.7 . . ? C11 C10 H10A 109.7 . . ? C9 C10 H10B 109.7 . . ? C11 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? C10 C11 C12 110.80(8) . . ? C10 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C7 C12 C11 111.86(8) . . ? C7 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? C7 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? N2 N1 C1 102.59(8) . . ? N3 N2 N1 117.35(8) . . ? N3 N2 C7 120.97(8) . . ? N1 N2 C7 120.85(8) . . ? N2 N3 C6 102.54(8) . . ? O1 N4 C7 114.84(14) . . ? O1B N4B O2B 133(2) . . ? O1B N4B C7 111(3) . . ? O2B N4B C7 116(3) . . ? 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 N1 C1 C2 C3 -179.27(10) . . . . ? C6 C1 C2 C3 0.50(14) . . . . ? C1 C2 C3 C4 -0.04(16) . . . . ? C2 C3 C4 C5 -0.35(18) . . . . ? C3 C4 C5 C6 0.25(16) . . . . ? N1 C1 C6 N3 0.11(11) . . . . ? C2 C1 C6 N3 -179.70(9) . . . . ? N1 C1 C6 C5 179.20(9) . . . . ? C2 C1 C6 C5 -0.61(15) . . . . ? C4 C5 C6 N3 179.10(10) . . . . ? C4 C5 C6 C1 0.22(15) . . . . ? N2 C7 C8 C9 72.52(10) . . . . ? C12 C7 C8 C9 -53.49(10) . . . . ? N4 C7 C8 C9 -167.52(11) . . . . ? N4B C7 C8 C9 -176.2(18) . . . . ? C7 C8 C9 C10 56.48(11) . . . . ? C8 C9 C10 C11 -58.45(11) . . . . ? C9 C10 C11 C12 57.30(11) . . . . ? N2 C7 C12 C11 -72.32(10) . . . . ? C8 C7 C12 C11 53.42(10) . . . . ? N4 C7 C12 C11 168.58(12) . . . . ? N4B C7 C12 C11 176.5(19) . . . . ? C10 C11 C12 C7 -55.29(11) . . . . ? C6 C1 N1 N2 -0.74(10) . . . . ? C2 C1 N1 N2 179.06(10) . . . . ? C1 N1 N2 N3 1.22(11) . . . . ? C1 N1 N2 C7 170.88(8) . . . . ? C8 C7 N2 N3 -155.63(8) . . . . ? C12 C7 N2 N3 -29.65(12) . . . . ? N4 C7 N2 N3 86.38(17) . . . . ? N4B C7 N2 N3 87(2) . . . . ? C8 C7 N2 N1 35.09(12) . . . . ? C12 C7 N2 N1 161.07(8) . . . . ? N4 C7 N2 N1 -82.90(17) . . . . ? N4B C7 N2 N1 -82(2) . . . . ? N1 N2 N3 C6 -1.16(11) . . . . ? C7 N2 N3 C6 -170.80(8) . . . . ? C1 C6 N3 N2 0.57(10) . . . . ? C5 C6 N3 N2 -178.43(10) . . . . ? N2 C7 N4 O1 -4.7(3) . . . . ? C8 C7 N4 O1 -125.6(3) . . . . ? C12 C7 N4 O1 115.7(3) . . . . ? N4B C7 N4 O1 -9(15) . . . . ? N2 C7 N4B O1B 174(4) . . . . ? C8 C7 N4B O1B 56(5) . . . . ? C12 C7 N4B O1B -68(5) . . . . ? N4 C7 N4B O1B -10(11) . . . . ? N2 C7 N4B O2B -5(5) . . . . ? C8 C7 N4B O2B -123(5) . . . . ? C12 C7 N4B O2B 113(5) . . . . ? N4 C7 N4B O2B 171(20) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.376 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.046 # Attachment '- Compound 6.cif' data_12mz117_0m _database_code_depnum_ccdc_archive 'CCDC 883510' #TrackingRef '- Compound 6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 N4 O2' _chemical_formula_weight 246.27 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 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 5.9246(9) _cell_length_b 11.7114(19) _cell_length_c 16.898(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1172.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3168 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 31.73 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6747 _exptl_absorpt_correction_T_max 0.7463 _exptl_absorpt_process_details 'Apex2 v2011.2-0 (Bruker, 2011)' _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 AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 8626 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 31.73 _reflns_number_total 2124 _reflns_number_gt 2045 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 v2011.2-0 (Bruker, 2011)' _computing_cell_refinement 'Apex2 v2011.2-0' _computing_data_reduction 'Apex2 v2011.2-0' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2003; Sheldrick, 2008)' _computing_structure_refinement ; SHELXLE Rev548, Shelxle (H\"ubschle et al., 2011) ; _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0524P)^2^+0.1709P] 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 2124 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0904 _refine_ls_wR_factor_gt 0.0888 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 0.8295(2) 1.01585(10) 0.01443(8) 0.0145(2) Uani 1 1 d . . . C2 C 0.6532(2) 1.04456(11) -0.04834(8) 0.0161(2) Uani 1 1 d . . . H2A H 0.7191 1.0976 -0.0877 0.019 Uiso 1 1 calc R . . H2B H 0.5229 1.0830 -0.0232 0.019 Uiso 1 1 calc R . . C3 C 0.5733(2) 0.93547(11) -0.09007(8) 0.0172(2) Uani 1 1 d . . . H3A H 0.4916 0.8868 -0.0517 0.021 Uiso 1 1 calc R . . H3B H 0.4667 0.9561 -0.1328 0.021 Uiso 1 1 calc R . . C4 C 0.7699(2) 0.86778(12) -0.12524(8) 0.0198(3) Uani 1 1 d . . . H4A H 0.7123 0.7966 -0.1496 0.024 Uiso 1 1 calc R . . H4B H 0.8442 0.9135 -0.1671 0.024 Uiso 1 1 calc R . . C5 C 0.9406(3) 0.83846(11) -0.06097(9) 0.0192(3) Uani 1 1 d . . . H5A H 1.0702 0.7979 -0.0849 0.023 Uiso 1 1 calc R . . H5B H 0.8696 0.7867 -0.0219 0.023 Uiso 1 1 calc R . . C6 C 1.0252(2) 0.94600(11) -0.01876(8) 0.0167(2) Uani 1 1 d . . . H6A H 1.1274 0.9238 0.0249 0.020 Uiso 1 1 calc R . . H6B H 1.1122 0.9934 -0.0565 0.020 Uiso 1 1 calc R . . C7 C 0.6992(2) 0.86445(11) 0.18696(8) 0.0172(3) Uani 1 1 d . . . C8 C 0.7195(3) 0.78665(12) 0.25099(8) 0.0216(3) Uani 1 1 d . . . H8 H 0.8501 0.7406 0.2579 0.026 Uiso 1 1 calc R . . C9 C 0.5411(3) 0.78146(12) 0.30226(9) 0.0240(3) Uani 1 1 d . . . H9 H 0.5475 0.7295 0.3454 0.029 Uiso 1 1 calc R . . C10 C 0.3452(3) 0.85165(13) 0.29304(8) 0.0229(3) Uani 1 1 d . . . H10 H 0.2274 0.8459 0.3310 0.028 Uiso 1 1 calc R . . C11 C 0.3213(3) 0.92708(12) 0.23139(8) 0.0200(3) Uani 1 1 d . . . H11 H 0.1904 0.9732 0.2256 0.024 Uiso 1 1 calc R . . C12 C 0.5029(2) 0.93218(11) 0.17684(8) 0.0167(2) Uani 1 1 d . . . N1 N 0.9373(2) 1.12872(10) 0.04570(8) 0.0214(3) Uani 1 1 d . . . N2 N 0.8427(2) 0.88520(10) 0.12656(7) 0.0171(2) Uani 1 1 d . . . N3 N 0.7277(2) 0.96120(9) 0.08312(7) 0.0152(2) Uani 1 1 d . . . N4 N 0.5248(2) 0.99377(10) 0.10969(7) 0.0165(2) Uani 1 1 d . . . O1 O 1.0250(3) 1.18992(9) -0.00405(7) 0.0337(3) Uani 1 1 d . . . O2 O 0.9340(2) 1.14810(10) 0.11666(7) 0.0310(3) 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 0.0162(5) 0.0132(5) 0.0143(5) -0.0028(4) 0.0017(5) -0.0020(4) C2 0.0180(6) 0.0151(5) 0.0154(6) 0.0003(4) 0.0008(5) 0.0014(5) C3 0.0164(6) 0.0189(5) 0.0164(6) -0.0018(5) -0.0014(5) -0.0003(5) C4 0.0195(6) 0.0221(6) 0.0179(6) -0.0065(5) 0.0007(5) 0.0017(5) C5 0.0194(6) 0.0175(5) 0.0209(6) -0.0042(5) 0.0015(5) 0.0039(5) C6 0.0125(5) 0.0201(5) 0.0175(6) -0.0033(5) 0.0022(5) 0.0009(5) C7 0.0184(6) 0.0193(5) 0.0140(6) -0.0020(4) -0.0026(5) -0.0020(5) C8 0.0273(7) 0.0214(6) 0.0160(6) 0.0017(5) -0.0050(6) -0.0017(6) C9 0.0349(8) 0.0222(6) 0.0149(6) 0.0010(5) -0.0020(6) -0.0075(6) C10 0.0271(7) 0.0261(6) 0.0156(6) -0.0039(5) 0.0030(6) -0.0099(6) C11 0.0184(6) 0.0243(6) 0.0173(6) -0.0043(5) 0.0021(5) -0.0045(5) C12 0.0179(6) 0.0187(5) 0.0137(6) -0.0032(4) -0.0011(5) -0.0025(5) N1 0.0205(6) 0.0178(5) 0.0260(6) -0.0075(4) 0.0013(5) -0.0029(4) N2 0.0163(5) 0.0186(5) 0.0163(5) -0.0001(4) -0.0021(4) 0.0011(4) N3 0.0150(5) 0.0168(5) 0.0137(5) -0.0009(4) 0.0011(4) 0.0009(4) N4 0.0146(5) 0.0192(5) 0.0157(5) -0.0024(4) 0.0016(4) 0.0006(4) O1 0.0430(8) 0.0228(5) 0.0352(6) -0.0020(5) 0.0051(6) -0.0156(5) O2 0.0347(6) 0.0331(6) 0.0252(6) -0.0150(5) 0.0036(5) -0.0083(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 N3 1.4562(17) . ? C1 C6 1.5256(18) . ? C1 C2 1.5260(19) . ? C1 N1 1.5602(17) . ? C2 C3 1.5341(18) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5290(19) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.523(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.5317(19) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N2 1.3502(18) . ? C7 C12 1.4180(19) . ? C7 C8 1.4196(18) . ? C8 C9 1.368(2) . ? C8 H8 0.9500 . ? C9 C10 1.431(2) . ? C9 H9 0.9500 . ? C10 C11 1.373(2) . ? C10 H10 0.9500 . ? C11 C12 1.4183(19) . ? C11 H11 0.9500 . ? C12 N4 1.3509(17) . ? N1 O2 1.2205(17) . ? N1 O1 1.2207(17) . ? N2 N3 1.3398(16) . ? N3 N4 1.3387(16) . ? 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 N3 C1 C6 111.84(11) . . ? N3 C1 C2 111.56(11) . . ? C6 C1 C2 112.50(11) . . ? N3 C1 N1 105.77(10) . . ? C6 C1 N1 105.54(10) . . ? C2 C1 N1 109.20(10) . . ? C1 C2 C3 110.32(10) . . ? C1 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 . . ? C1 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C4 C3 C2 112.05(11) . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3B 109.2 . . ? C2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C5 C4 C3 110.21(11) . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C4 C5 C6 111.34(11) . . ? C4 C5 H5A 109.4 . . ? C6 C5 H5A 109.4 . . ? C4 C5 H5B 109.4 . . ? C6 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? C1 C6 C5 111.31(11) . . ? C1 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? C1 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? N2 C7 C12 108.94(12) . . ? N2 C7 C8 129.66(14) . . ? C12 C7 C8 121.36(13) . . ? C9 C8 C7 116.47(14) . . ? C9 C8 H8 121.8 . . ? C7 C8 H8 121.8 . . ? C8 C9 C10 122.15(13) . . ? C8 C9 H9 118.9 . . ? C10 C9 H9 118.9 . . ? C11 C10 C9 122.42(14) . . ? C11 C10 H10 118.8 . . ? C9 C10 H10 118.8 . . ? C10 C11 C12 116.21(14) . . ? C10 C11 H11 121.9 . . ? C12 C11 H11 121.9 . . ? N4 C12 C7 108.73(12) . . ? N4 C12 C11 129.89(13) . . ? C7 C12 C11 121.37(13) . . ? O2 N1 O1 125.04(13) . . ? O2 N1 C1 118.93(12) . . ? O1 N1 C1 116.00(12) . . ? N3 N2 C7 102.34(11) . . ? N4 N3 N2 117.52(11) . . ? N4 N3 C1 120.93(11) . . ? N2 N3 C1 121.22(11) . . ? N3 N4 C12 102.46(11) . . ? 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 N3 C1 C2 C3 -73.00(13) . . . . ? C6 C1 C2 C3 53.62(14) . . . . ? N1 C1 C2 C3 170.45(11) . . . . ? C1 C2 C3 C4 -55.23(15) . . . . ? C2 C3 C4 C5 56.93(15) . . . . ? C3 C4 C5 C6 -56.39(15) . . . . ? N3 C1 C6 C5 72.44(14) . . . . ? C2 C1 C6 C5 -54.04(15) . . . . ? N1 C1 C6 C5 -173.02(11) . . . . ? C4 C5 C6 C1 55.17(16) . . . . ? N2 C7 C8 C9 -177.71(14) . . . . ? C12 C7 C8 C9 -0.5(2) . . . . ? C7 C8 C9 C10 -1.0(2) . . . . ? C8 C9 C10 C11 1.3(2) . . . . ? C9 C10 C11 C12 -0.2(2) . . . . ? N2 C7 C12 N4 0.62(15) . . . . ? C8 C7 C12 N4 -177.13(12) . . . . ? N2 C7 C12 C11 179.37(12) . . . . ? C8 C7 C12 C11 1.62(19) . . . . ? C10 C11 C12 N4 177.23(13) . . . . ? C10 C11 C12 C7 -1.23(19) . . . . ? N3 C1 N1 O2 4.64(17) . . . . ? C6 C1 N1 O2 -114.03(15) . . . . ? C2 C1 N1 O2 124.81(14) . . . . ? N3 C1 N1 O1 -177.30(14) . . . . ? C6 C1 N1 O1 64.04(16) . . . . ? C2 C1 N1 O1 -57.12(16) . . . . ? C12 C7 N2 N3 -0.95(14) . . . . ? C8 C7 N2 N3 176.55(14) . . . . ? C7 N2 N3 N4 1.08(15) . . . . ? C7 N2 N3 C1 174.42(11) . . . . ? C6 C1 N3 N4 -164.47(11) . . . . ? C2 C1 N3 N4 -37.48(15) . . . . ? N1 C1 N3 N4 81.14(13) . . . . ? C6 C1 N3 N2 22.42(16) . . . . ? C2 C1 N3 N2 149.40(11) . . . . ? N1 C1 N3 N2 -91.98(13) . . . . ? N2 N3 N4 C12 -0.71(14) . . . . ? C1 N3 N4 C12 -174.07(11) . . . . ? C7 C12 N4 N3 0.02(13) . . . . ? C11 C12 N4 N3 -178.59(13) . . . . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.312 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.042