# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_ke1006m _database_code_depnum_ccdc_archive 'CCDC 898798' #TrackingRef 'ke1006m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; KETA 1,3,5-tris-[CH(=NOH)]-benzene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H9 N3 O3' _chemical_formula_sum 'C9 H9 N3 O3' _chemical_formula_weight 207.19 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 Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 16.6967(11) _cell_length_b 4.2787(3) _cell_length_c 13.1262(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 937.74(11) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7177 _cell_measurement_theta_min 3.10 _cell_measurement_theta_max 32.59 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.468 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9668 _exptl_absorpt_correction_T_max 0.9843 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 11730 _diffrn_reflns_av_R_equivalents 0.0592 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 33.38 _reflns_number_total 1780 _reflns_number_gt 1489 _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^)+(0.0550P)^2^+0.4000P] 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 1780 _refine_ls_number_parameters 145 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0636 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1302 _refine_ls_wR_factor_gt 0.1190 _refine_ls_goodness_of_fit_ref 1.164 _refine_ls_restrained_S_all 1.163 _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 C11 C 0.21012(14) 0.4850(6) 0.35713(18) 0.0183(4) Uani 1 1 d . . . C12 C 0.22874(14) 0.2768(6) 0.27816(19) 0.0184(4) Uani 1 1 d . . . H12 H 0.1899 0.2320 0.2273 0.022 Uiso 1 1 calc R . . C13 C 0.30399(14) 0.1346(6) 0.27371(18) 0.0180(4) Uani 1 1 d . . . C14 C 0.36108(14) 0.2048(6) 0.34856(18) 0.0181(4) Uani 1 1 d . . . H14 H 0.4125 0.1097 0.3457 0.022 Uiso 1 1 calc R . . C15 C 0.34325(14) 0.4127(6) 0.42709(17) 0.0174(4) Uani 1 1 d . . . C16 C 0.26710(14) 0.5524(6) 0.43130(18) 0.0186(4) Uani 1 1 d . . . H16 H 0.2545 0.6931 0.4849 0.022 Uiso 1 1 calc R . . C21 C 0.13312(15) 0.6506(6) 0.36379(19) 0.0203(5) Uani 1 1 d . . . H21A H 0.1242 0.7848 0.4203 0.024 Uiso 1 1 calc R . . N21 N 0.07767(12) 0.6229(5) 0.29731(16) 0.0192(4) Uani 1 1 d . . . O21 O 0.01244(11) 0.8131(5) 0.32295(15) 0.0234(4) Uani 1 1 d . . . H21 H -0.023(2) 0.764(8) 0.268(3) 0.028 Uiso 1 1 d . . . C23 C 0.32022(14) -0.0851(6) 0.19032(18) 0.0191(5) Uani 1 1 d . . . H23A H 0.2799 -0.1233 0.1408 0.023 Uiso 1 1 calc R . . N23 N 0.38763(13) -0.2266(5) 0.18277(16) 0.0191(4) Uani 1 1 d . . . O23 O 0.38904(12) -0.4282(5) 0.09840(14) 0.0238(4) Uani 1 1 d . . . H23 H 0.436(2) -0.525(8) 0.110(3) 0.029 Uiso 1 1 d . . . C25 C 0.40652(15) 0.4846(6) 0.50146(18) 0.0205(5) Uani 1 1 d . . . H25A H 0.4564 0.3786 0.4977 0.025 Uiso 1 1 calc R . . N25 N 0.39488(13) 0.6882(6) 0.57091(17) 0.0213(4) Uani 1 1 d . . . O25 O 0.46436(12) 0.7300(5) 0.63027(15) 0.0255(4) Uani 1 1 d . . . H25 H 0.447(2) 0.857(9) 0.688(3) 0.031 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 C11 0.0143(9) 0.0202(11) 0.0204(10) 0.0031(9) -0.0002(8) -0.0011(8) C12 0.0172(10) 0.0186(11) 0.0193(10) 0.0002(8) -0.0032(8) -0.0006(8) C13 0.0177(10) 0.0163(10) 0.0200(9) 0.0016(9) -0.0004(8) -0.0012(8) C14 0.0159(10) 0.0193(11) 0.0190(10) -0.0005(9) -0.0007(8) 0.0010(8) C15 0.0167(10) 0.0179(10) 0.0176(9) 0.0014(8) -0.0011(7) -0.0029(9) C16 0.0170(10) 0.0194(11) 0.0193(10) -0.0010(8) 0.0004(8) -0.0009(8) C21 0.0179(11) 0.0219(12) 0.0212(11) -0.0019(9) 0.0002(8) 0.0009(9) N21 0.0150(8) 0.0212(10) 0.0215(9) -0.0006(8) 0.0021(7) 0.0005(7) O21 0.0156(8) 0.0299(10) 0.0247(9) -0.0032(8) -0.0019(7) 0.0039(7) C23 0.0173(10) 0.0213(12) 0.0189(10) 0.0019(9) -0.0030(8) -0.0012(8) N23 0.0196(9) 0.0193(10) 0.0183(8) 0.0001(8) 0.0008(7) -0.0024(7) O23 0.0226(9) 0.0278(10) 0.0210(8) -0.0048(7) -0.0016(7) 0.0040(7) C25 0.0176(10) 0.0251(12) 0.0187(10) 0.0008(9) -0.0003(8) 0.0027(9) N25 0.0156(9) 0.0280(12) 0.0205(9) -0.0012(8) -0.0045(7) 0.0000(8) O25 0.0179(8) 0.0364(11) 0.0220(8) -0.0082(8) -0.0046(7) 0.0031(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 C11 C16 1.391(3) . ? C11 C12 1.402(3) . ? C11 C21 1.471(3) . ? C12 C13 1.397(3) . ? C12 H12 0.9500 . ? C13 C14 1.401(3) . ? C13 C23 1.468(3) . ? C14 C15 1.394(3) . ? C14 H14 0.9500 . ? C15 C16 1.406(3) . ? C15 C25 1.471(3) . ? C16 H16 0.9500 . ? C21 N21 1.278(3) . ? C21 H21A 0.9500 . ? N21 O21 1.401(3) . ? O21 H21 0.96(4) . ? C23 N23 1.282(3) . ? C23 H23A 0.9500 . ? N23 O23 1.404(3) . ? O23 H23 0.89(4) . ? C25 N25 1.276(3) . ? C25 H25A 0.9500 . ? N25 O25 1.409(3) . ? O25 H25 0.97(4) . ? 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 C16 C11 C12 119.8(2) . . ? C16 C11 C21 117.1(2) . . ? C12 C11 C21 123.0(2) . . ? C13 C12 C11 120.5(2) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 119.3(2) . . ? C12 C13 C23 118.4(2) . . ? C14 C13 C23 122.3(2) . . ? C15 C14 C13 120.7(2) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 119.6(2) . . ? C14 C15 C25 118.1(2) . . ? C16 C15 C25 122.3(2) . . ? C11 C16 C15 120.2(2) . . ? C11 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? N21 C21 C11 123.2(2) . . ? N21 C21 H21A 118.4 . . ? C11 C21 H21A 118.4 . . ? C21 N21 O21 110.2(2) . . ? N21 O21 H21 100(2) . . ? N23 C23 C13 121.5(2) . . ? N23 C23 H23A 119.3 . . ? C13 C23 H23A 119.3 . . ? C23 N23 O23 111.5(2) . . ? N23 O23 H23 100(2) . . ? N25 C25 C15 120.5(2) . . ? N25 C25 H25A 119.7 . . ? C15 C25 H25A 119.7 . . ? C25 N25 O25 110.9(2) . . ? N25 O25 H25 105(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 C16 C11 C12 C13 0.4(4) . . . . ? C21 C11 C12 C13 177.6(2) . . . . ? C11 C12 C13 C14 -0.6(4) . . . . ? C11 C12 C13 C23 179.1(2) . . . . ? C12 C13 C14 C15 0.3(4) . . . . ? C23 C13 C14 C15 -179.5(2) . . . . ? C13 C14 C15 C16 0.2(4) . . . . ? C13 C14 C15 C25 -178.1(2) . . . . ? C12 C11 C16 C15 0.1(4) . . . . ? C21 C11 C16 C15 -177.3(2) . . . . ? C14 C15 C16 C11 -0.4(4) . . . . ? C25 C15 C16 C11 177.8(2) . . . . ? C16 C11 C21 N21 175.9(2) . . . . ? C12 C11 C21 N21 -1.4(4) . . . . ? C11 C21 N21 O21 -178.8(2) . . . . ? C12 C13 C23 N23 -179.0(2) . . . . ? C14 C13 C23 N23 0.8(4) . . . . ? C13 C23 N23 O23 179.0(2) . . . . ? C14 C15 C25 N25 175.5(2) . . . . ? C16 C15 C25 N25 -2.7(4) . . . . ? C15 C25 N25 O25 -177.2(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 O21 H21 N23 0.96(4) 1.87(4) 2.804(3) 164(4) 3_455 O23 H23 O25 0.89(4) 1.91(4) 2.799(3) 179(3) 2_654 O25 H25 N21 0.97(4) 1.88(4) 2.851(3) 175(3) 4 _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.309 _refine_diff_density_min -0.420 _refine_diff_density_rms 0.079