# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2003 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 loop_ _publ_author_name J.Tatiersky J.Marek P.Schwendt M.Sivak _publ_contact_author_name J.Tatiersky _publ_contact_author_email tatiersky@fns.uniba.sk _publ_section_title ; Racemic Vanadium(V) Oxo Monoperoxo Complexes with Two Achiral Bidentate Heteroligands. Synthesis, Characterization, Crystal Structure and Stereochemistry of K[VO(O2)(ox)(bpy)] · 3H2O and Pr4N[VO(O2)(ox)(phen)] ; data_fp_a _database_code_depnum_ccdc_archive 'CCDC 212922' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H36 N3 O7 V' _chemical_formula_weight 553.52 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' V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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' '-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 29.5519(12) _cell_length_b 10.0503(5) _cell_length_c 19.3160(9) _cell_angle_alpha 90.00 _cell_angle_beta 112.005(4) _cell_angle_gamma 90.00 _cell_volume 5319.0(4) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2336 _exptl_absorpt_coefficient_mu 0.422 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9203 _exptl_absorpt_correction_T_max 0.9590 _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14505 _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_sigmaI/netI 0.0399 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4654 _reflns_number_gt 3811 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0500P)^2^+7.5000P] 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 0.00017(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4654 _refine_ls_number_parameters 479 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0576 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1021 _refine_ls_wR_factor_gt 0.0954 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 V1 V 0.093938(15) 0.32306(4) 0.47751(2) 0.02022(14) Uani 1 1 d . . . O1 O 0.05693(6) 0.43096(17) 0.48807(9) 0.0264(4) Uani 1 1 d . . . O2 O 0.05412(6) 0.18606(18) 0.42354(10) 0.0320(4) Uani 1 1 d . . . O3 O 0.06279(6) 0.28050(18) 0.37556(10) 0.0299(4) Uani 1 1 d . . . O4 O 0.10023(7) 0.19172(17) 0.55897(10) 0.0304(4) Uani 1 1 d . . . O5 O 0.15163(6) 0.39865(16) 0.56511(9) 0.0222(4) Uani 1 1 d . . . O6 O 0.13724(9) 0.1500(2) 0.68050(12) 0.0509(6) Uani 1 1 d . . . O7 O 0.18970(7) 0.38768(18) 0.68867(9) 0.0307(4) Uani 1 1 d . . . N1 N 0.12541(7) 0.46065(19) 0.42287(10) 0.0190(4) Uani 1 1 d . . . N2 N 0.15822(7) 0.21296(19) 0.46103(11) 0.0208(5) Uani 1 1 d . . . N3 N 0.08648(7) 0.75370(19) 0.63847(10) 0.0194(4) Uani 1 1 d . . . C1 C 0.13074(10) 0.2178(3) 0.62552(15) 0.0294(6) Uani 1 1 d . . . C2 C 0.16038(9) 0.3460(2) 0.62932(14) 0.0223(5) Uani 1 1 d . . . C3 C 0.10895(10) 0.5839(2) 0.40443(14) 0.0244(6) Uani 1 1 d . . . H3 H 0.0835(9) 0.606(2) 0.4154(12) 0.012(6) Uiso 1 1 d . . . C4 C 0.12744(10) 0.6699(3) 0.36506(14) 0.0277(6) Uani 1 1 d . . . H4 H 0.1144(9) 0.757(3) 0.3536(14) 0.029(7) Uiso 1 1 d . . . C5 C 0.16293(10) 0.6269(3) 0.34140(14) 0.0254(6) Uani 1 1 d . . . H5 H 0.1737(9) 0.682(3) 0.3139(14) 0.027(7) Uiso 1 1 d . . . C6 C 0.18113(8) 0.4963(2) 0.35915(12) 0.0209(5) Uani 1 1 d . . . C7 C 0.16148(8) 0.4174(2) 0.40098(12) 0.0185(5) Uani 1 1 d . . . C8 C 0.17862(8) 0.2830(2) 0.42032(12) 0.0193(5) Uani 1 1 d . . . C9 C 0.21401(9) 0.2313(3) 0.39592(13) 0.0233(5) Uani 1 1 d . . . C10 C 0.22906(10) 0.0993(3) 0.41611(16) 0.0302(6) Uani 1 1 d . . . H10 H 0.2532(10) 0.068(3) 0.4030(15) 0.031(7) Uiso 1 1 d . . . C11 C 0.20867(10) 0.0293(3) 0.45746(17) 0.0330(7) Uani 1 1 d . . . H11 H 0.2176(10) -0.050(3) 0.4716(15) 0.031(8) Uiso 1 1 d . . . C12 C 0.17344(10) 0.0889(3) 0.47892(15) 0.0272(6) Uani 1 1 d . . . H12 H 0.1581(9) 0.043(3) 0.5067(14) 0.025(7) Uiso 1 1 d . . . C13 C 0.21676(9) 0.4397(3) 0.33411(14) 0.0264(6) Uani 1 1 d . . . H13 H 0.2295(9) 0.494(3) 0.3036(14) 0.024(7) Uiso 1 1 d . . . C14 C 0.23221(9) 0.3133(3) 0.35118(14) 0.0270(6) Uani 1 1 d . . . H14 H 0.2537(10) 0.277(3) 0.3319(14) 0.028(7) Uiso 1 1 d . . . C15 C 0.13331(9) 0.6980(3) 0.63441(16) 0.0250(6) Uani 1 1 d . . . H15A H 0.1489(10) 0.641(3) 0.6788(15) 0.032(7) Uiso 1 1 d . . . H15B H 0.1239(10) 0.635(3) 0.5914(15) 0.029(7) Uiso 1 1 d . . . C16 C 0.16980(10) 0.8011(3) 0.63019(19) 0.0347(7) Uani 1 1 d . . . H16A H 0.1843(10) 0.844(3) 0.6783(16) 0.033(8) Uiso 1 1 d . . . H16B H 0.1530(11) 0.870(3) 0.5894(18) 0.051(9) Uiso 1 1 d . . . C17 C 0.20933(14) 0.7308(4) 0.6112(3) 0.0553(10) Uani 1 1 d . . . H17A H 0.1954(15) 0.695(4) 0.563(2) 0.077(13) Uiso 1 1 d . . . H17B H 0.2319(12) 0.793(3) 0.6079(17) 0.048(9) Uiso 1 1 d . . . H17C H 0.2304(17) 0.665(5) 0.660(3) 0.106(16) Uiso 1 1 d . . . C18 C 0.05250(9) 0.6379(2) 0.63622(14) 0.0198(5) Uani 1 1 d . . . H18A H 0.0494(8) 0.590(2) 0.5924(13) 0.013(6) Uiso 1 1 d . . . H18B H 0.0225(10) 0.681(3) 0.6328(14) 0.025(7) Uiso 1 1 d . . . C19 C 0.07026(10) 0.5410(3) 0.70053(15) 0.0268(6) Uani 1 1 d . . . H19A H 0.0729(9) 0.587(3) 0.7457(15) 0.027(7) Uiso 1 1 d . . . H19B H 0.1014(10) 0.510(3) 0.7045(14) 0.032(7) Uiso 1 1 d . . . C20 C 0.03404(13) 0.4258(3) 0.68299(19) 0.0420(8) Uani 1 1 d . . . H20A H 0.0434(12) 0.358(4) 0.7215(19) 0.060(10) Uiso 1 1 d . . . H20B H 0.0305(12) 0.379(3) 0.635(2) 0.053(10) Uiso 1 1 d . . . H20C H 0.0019(13) 0.456(3) 0.6751(18) 0.057(11) Uiso 1 1 d . . . C21 C 0.09901(10) 0.8349(3) 0.70941(14) 0.0237(5) Uani 1 1 d . . . H21A H 0.1173(8) 0.779(2) 0.7469(13) 0.011(6) Uiso 1 1 d . . . H21B H 0.1197(9) 0.906(3) 0.7041(13) 0.019(6) Uiso 1 1 d . . . C22 C 0.05593(11) 0.8887(3) 0.72447(15) 0.0289(6) Uani 1 1 d . . . H22A H 0.0390(11) 0.813(3) 0.7392(16) 0.037(8) Uiso 1 1 d . . . H22B H 0.0329(11) 0.927(3) 0.6825(17) 0.040(8) Uiso 1 1 d . . . C23 C 0.07369(14) 0.9925(3) 0.78615(18) 0.0375(7) Uani 1 1 d . . . H23A H 0.0969(13) 0.959(3) 0.833(2) 0.058(10) Uiso 1 1 d . . . H23B H 0.0889(12) 1.057(3) 0.7705(18) 0.052(10) Uiso 1 1 d . . . H23C H 0.0446(13) 1.031(3) 0.7957(18) 0.057(10) Uiso 1 1 d . . . C24 C 0.06001(10) 0.8428(2) 0.57237(13) 0.0206(5) Uani 1 1 d . . . H24A H 0.0779(9) 0.924(3) 0.5831(14) 0.024(7) Uiso 1 1 d . . . H24B H 0.0284(9) 0.853(2) 0.5732(12) 0.011(6) Uiso 1 1 d . . . C25 C 0.05507(10) 0.7871(3) 0.49720(14) 0.0254(6) Uani 1 1 d . . . H25A H 0.0891(10) 0.789(3) 0.4942(14) 0.028(7) Uiso 1 1 d . . . H25B H 0.0428(10) 0.695(3) 0.4917(14) 0.031(7) Uiso 1 1 d . . . C26 C 0.02042(11) 0.8718(3) 0.43500(15) 0.0292(6) Uani 1 1 d . . . H26A H -0.0116(11) 0.868(3) 0.4378(15) 0.033(8) Uiso 1 1 d . . . H26B H 0.0329(10) 0.967(3) 0.4433(16) 0.042(8) Uiso 1 1 d . . . H26C H 0.0189(11) 0.836(3) 0.3847(17) 0.045(9) 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 V1 0.0191(2) 0.0181(2) 0.0245(2) -0.00297(18) 0.00944(17) -0.00160(17) O1 0.0246(10) 0.0269(10) 0.0308(10) -0.0046(8) 0.0138(8) -0.0009(7) O2 0.0284(10) 0.0286(10) 0.0401(11) -0.0081(9) 0.0142(9) -0.0072(8) O3 0.0277(10) 0.0288(10) 0.0316(10) -0.0084(8) 0.0093(8) -0.0031(8) O4 0.0328(10) 0.0252(10) 0.0383(11) 0.0020(8) 0.0192(9) -0.0048(8) O5 0.0248(9) 0.0222(9) 0.0204(9) -0.0013(7) 0.0093(7) -0.0030(7) O6 0.0668(16) 0.0422(13) 0.0459(13) 0.0207(11) 0.0235(12) -0.0024(11) O7 0.0361(11) 0.0339(11) 0.0209(9) -0.0031(8) 0.0096(9) 0.0057(9) N1 0.0202(10) 0.0190(10) 0.0166(10) -0.0037(8) 0.0055(8) 0.0010(8) N2 0.0206(11) 0.0177(11) 0.0210(10) -0.0017(8) 0.0041(9) -0.0009(8) N3 0.0209(10) 0.0154(10) 0.0199(10) -0.0013(8) 0.0056(9) -0.0003(8) C1 0.0332(15) 0.0269(14) 0.0342(15) 0.0064(12) 0.0195(13) 0.0052(12) C2 0.0261(13) 0.0195(13) 0.0260(14) 0.0015(11) 0.0153(11) 0.0092(10) C3 0.0282(15) 0.0229(14) 0.0216(13) -0.0039(11) 0.0089(11) 0.0058(11) C4 0.0362(15) 0.0194(14) 0.0232(13) 0.0035(11) 0.0062(11) 0.0063(12) C5 0.0274(14) 0.0258(14) 0.0207(13) 0.0028(11) 0.0063(11) -0.0034(11) C6 0.0192(12) 0.0247(13) 0.0144(11) 0.0010(10) 0.0011(10) -0.0012(10) C7 0.0160(12) 0.0212(12) 0.0134(11) -0.0028(10) -0.0003(9) -0.0012(10) C8 0.0162(12) 0.0212(13) 0.0162(11) -0.0031(10) 0.0012(10) -0.0007(9) C9 0.0182(12) 0.0254(13) 0.0223(12) -0.0039(11) 0.0029(10) 0.0017(10) C10 0.0202(14) 0.0300(15) 0.0386(16) -0.0032(12) 0.0091(12) 0.0059(12) C11 0.0295(15) 0.0188(14) 0.0469(18) 0.0017(13) 0.0100(13) 0.0060(12) C12 0.0278(14) 0.0202(14) 0.0309(15) 0.0011(11) 0.0077(12) -0.0016(11) C13 0.0230(14) 0.0363(16) 0.0194(13) 0.0019(11) 0.0073(11) 0.0000(12) C14 0.0180(13) 0.0378(16) 0.0257(13) -0.0017(12) 0.0088(11) 0.0047(12) C15 0.0198(13) 0.0207(14) 0.0337(15) 0.0008(12) 0.0093(12) 0.0030(10) C16 0.0254(15) 0.0299(16) 0.0509(19) -0.0035(14) 0.0167(14) -0.0031(12) C17 0.038(2) 0.049(2) 0.091(3) -0.020(2) 0.039(2) -0.0150(17) C18 0.0197(13) 0.0184(13) 0.0202(13) -0.0017(10) 0.0062(10) -0.0029(10) C19 0.0298(15) 0.0230(14) 0.0239(14) 0.0030(11) 0.0060(12) -0.0017(12) C20 0.045(2) 0.0375(18) 0.0337(18) 0.0120(15) 0.0033(15) -0.0144(15) C21 0.0276(14) 0.0192(13) 0.0187(12) -0.0013(11) 0.0025(11) -0.0036(12) C22 0.0354(16) 0.0325(16) 0.0191(13) -0.0040(12) 0.0107(12) 0.0006(13) C23 0.057(2) 0.0309(17) 0.0326(17) -0.0097(13) 0.0255(16) -0.0116(16) C24 0.0247(14) 0.0167(13) 0.0217(13) 0.0006(10) 0.0100(11) 0.0017(11) C25 0.0368(16) 0.0195(14) 0.0226(13) 0.0001(10) 0.0140(12) 0.0009(11) C26 0.0394(17) 0.0261(15) 0.0223(14) 0.0011(11) 0.0119(13) -0.0017(13) _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 V1 O1 1.6065(17) . ? V1 O2 1.8569(18) . ? V1 O3 1.8841(18) . ? V1 O4 2.0084(18) . ? V1 O5 2.0458(17) . ? V1 N1 2.151(2) . ? V1 N2 2.321(2) . ? O2 O3 1.415(2) . ? O4 C1 1.291(3) . ? O5 C2 1.282(3) . ? O6 C1 1.215(3) . ? O7 C2 1.223(3) . ? N1 C3 1.330(3) . ? N1 C7 1.357(3) . ? N2 C12 1.327(3) . ? N2 C8 1.354(3) . ? N3 C24 1.515(3) . ? N3 C21 1.517(3) . ? N3 C15 1.522(3) . ? N3 C18 1.527(3) . ? C1 C2 1.544(4) . ? C3 C4 1.391(4) . ? C4 C5 1.362(4) . ? C5 C6 1.411(4) . ? C6 C7 1.404(3) . ? C6 C13 1.431(3) . ? C7 C8 1.442(3) . ? C8 C9 1.398(3) . ? C9 C10 1.406(4) . ? C9 C14 1.437(4) . ? C10 C11 1.363(4) . ? C11 C12 1.392(4) . ? C13 C14 1.348(4) . ? C15 C16 1.519(4) . ? C16 C17 1.524(4) . ? C18 C19 1.509(3) . ? C19 C20 1.526(4) . ? C21 C22 1.509(4) . ? C22 C23 1.521(4) . ? C24 C25 1.511(3) . ? C25 C26 1.515(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 O1 V1 O2 104.68(9) . . ? O1 V1 O3 101.34(8) . . ? O2 V1 O3 44.46(8) . . ? O1 V1 O4 102.22(8) . . ? O2 V1 O4 78.79(8) . . ? O3 V1 O4 122.36(8) . . ? O1 V1 O5 92.31(8) . . ? O2 V1 O5 153.66(8) . . ? O3 V1 O5 151.42(7) . . ? O4 V1 O5 78.01(7) . . ? O1 V1 N1 93.92(8) . . ? O2 V1 N1 120.05(8) . . ? O3 V1 N1 76.40(7) . . ? O4 V1 N1 151.27(8) . . ? O5 V1 N1 77.73(7) . . ? O1 V1 N2 166.00(8) . . ? O2 V1 N2 87.05(7) . . ? O3 V1 N2 81.54(7) . . ? O4 V1 N2 87.36(7) . . ? O5 V1 N2 79.59(7) . . ? N1 V1 N2 73.30(7) . . ? O3 O2 V1 68.79(10) . . ? O2 O3 V1 66.75(10) . . ? C1 O4 V1 118.15(16) . . ? C2 O5 V1 116.77(15) . . ? C3 N1 C7 117.8(2) . . ? C3 N1 V1 123.26(17) . . ? C7 N1 V1 118.77(15) . . ? C12 N2 C8 117.3(2) . . ? C12 N2 V1 128.85(17) . . ? C8 N2 V1 113.41(15) . . ? C24 N3 C21 108.50(18) . . ? C24 N3 C15 111.49(18) . . ? C21 N3 C15 108.99(19) . . ? C24 N3 C18 107.47(18) . . ? C21 N3 C18 111.80(19) . . ? C15 N3 C18 108.61(18) . . ? O6 C1 O4 125.4(3) . . ? O6 C1 C2 121.7(3) . . ? O4 C1 C2 112.9(2) . . ? O7 C2 O5 125.5(2) . . ? O7 C2 C1 121.3(2) . . ? O5 C2 C1 113.1(2) . . ? N1 C3 C4 123.1(2) . . ? C5 C4 C3 119.8(2) . . ? C4 C5 C6 119.0(2) . . ? C7 C6 C5 117.6(2) . . ? C7 C6 C13 119.0(2) . . ? C5 C6 C13 123.3(2) . . ? N1 C7 C6 122.7(2) . . ? N1 C7 C8 117.4(2) . . ? C6 C7 C8 119.8(2) . . ? N2 C8 C9 123.7(2) . . ? N2 C8 C7 116.6(2) . . ? C9 C8 C7 119.7(2) . . ? C8 C9 C10 117.1(2) . . ? C8 C9 C14 119.0(2) . . ? C10 C9 C14 123.9(2) . . ? C11 C10 C9 119.1(3) . . ? C10 C11 C12 119.8(3) . . ? N2 C12 C11 123.0(3) . . ? C14 C13 C6 121.1(2) . . ? C13 C14 C9 121.3(2) . . ? C16 C15 N3 115.4(2) . . ? C15 C16 C17 108.7(3) . . ? C19 C18 N3 116.5(2) . . ? C18 C19 C20 107.9(2) . . ? C22 C21 N3 115.4(2) . . ? C21 C22 C23 109.2(2) . . ? C25 C24 N3 115.1(2) . . ? C24 C25 C26 110.3(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.810 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.051 data_fp _database_code_depnum_ccdc_archive 'CCDC 212923' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C12 H14 K N2 O10 V' _chemical_formula_weight 436.29 _chemical_melting_point ? _chemical_compound_source ? 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' K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 9.6777(5) _cell_length_b 13.8879(6) _cell_length_c 12.7353(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.606(5) _cell_angle_gamma 90.00 _cell_volume 1696.60(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.708 _exptl_crystal_density_method ? _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.887 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9593 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2968 _reflns_number_observed 2603 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 62 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+1.5000P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2906 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0301 _refine_ls_R_factor_obs 0.0245 _refine_ls_wR_factor_all 0.0634 _refine_ls_wR_factor_obs 0.0615 _refine_ls_goodness_of_fit_all 1.004 _refine_ls_goodness_of_fit_obs 1.038 _refine_ls_restrained_S_all 0.995 _refine_ls_restrained_S_obs 1.038 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group V1 V 0.36396(3) 0.15202(2) 0.09396(2) 0.01288(10) Uani 1 d . . K1 K 0.59409(4) 0.35350(3) 0.04327(3) 0.01648(11) Uani 1 d . . O1 O 0.51268(13) 0.12606(10) 0.05897(11) 0.0208(3) Uani 1 d . . O2 O 0.33212(13) 0.27306(9) 0.02568(10) 0.0199(3) Uani 1 d . . O3 O 0.38243(14) 0.28033(9) 0.13669(10) 0.0200(3) Uani 1 d . . O4 O 0.31323(13) 0.01076(9) 0.12252(10) 0.0160(3) Uani 1 d . . O5 O 0.41509(13) 0.14006(9) 0.25300(10) 0.0175(3) Uani 1 d . . O6 O 0.31365(13) -0.10072(9) 0.24901(10) 0.0182(3) Uani 1 d . . O7 O 0.45884(15) 0.03438(10) 0.38522(10) 0.0233(3) Uani 1 d . . O8 O 0.8787(2) 0.5943(2) 0.0394(2) 0.0365(4) Uani 1 d . . O9 O 0.1588(2) 0.59713(12) 0.03194(14) 0.0304(4) Uani 1 d . . O10 O 0.3408(2) -0.27502(11) 0.14823(12) 0.0233(3) Uani 1 d . . N1 N 0.2507(2) 0.10935(11) -0.05348(12) 0.0145(3) Uani 1 d . . N2 N 0.1361(2) 0.16330(10) 0.11388(12) 0.0140(3) Uani 1 d . . C1 C 0.3394(2) -0.01985(13) 0.21726(14) 0.0139(4) Uani 1 d . . C2 C 0.4111(2) 0.05584(13) 0.29481(15) 0.0156(4) Uani 1 d . . C3 C 0.3162(2) 0.08313(14) -0.1356(2) 0.0203(4) Uani 1 d . . C4 C 0.2449(2) 0.05627(15) -0.2321(2) 0.0235(4) Uani 1 d . . C5 C 0.1010(2) 0.05637(14) -0.2452(2) 0.0235(5) Uani 1 d . . C6 C 0.0328(2) 0.08294(14) -0.1609(2) 0.0201(4) Uani 1 d . . C7 C 0.1091(2) 0.10901(13) -0.06575(15) 0.0141(4) Uani 1 d . . C8 C 0.0449(2) 0.13808(12) 0.02908(15) 0.0144(4) Uani 1 d . . C9 C -0.0982(2) 0.13922(14) 0.0324(2) 0.0188(4) Uani 1 d . . C10 C -0.1468(2) 0.16776(14) 0.1249(2) 0.0220(4) Uani 1 d . . C11 C -0.0533(2) 0.19539(14) 0.2106(2) 0.0223(4) Uani 1 d . . C12 C 0.0878(2) 0.19187(14) 0.2023(2) 0.0181(4) Uani 1 d . . H3 H 0.4138(25) 0.0803(16) -0.1203(17) 0.025(6) Uiso 1 d . . H4 H 0.2922(24) 0.0388(17) -0.2841(19) 0.029(6) Uiso 1 d . . H5 H 0.0529(24) 0.0370(17) -0.3074(18) 0.027(6) Uiso 1 d . . H6 H -0.0625(25) 0.0843(16) -0.1680(17) 0.027(6) Uiso 1 d . . H8V H 0.8330(33) 0.6328(24) 0.0154(24) 0.052(10) Uiso 1 d . . H8W H 0.8526(31) 0.5433(25) 0.0203(24) 0.055(10) Uiso 1 d . . H9 H -0.1555(22) 0.1209(15) -0.0211(17) 0.015(5) Uiso 1 d . . H9V H 0.2015(28) 0.6340(20) 0.0780(22) 0.040(8) Uiso 1 d . . H9W H 0.0797(34) 0.6054(22) 0.0299(23) 0.050(9) Uiso 1 d . . H10 H -0.2421(26) 0.1668(16) 0.1302(18) 0.029(6) Uiso 1 d . . H10V H 0.3312(26) -0.2225(20) 0.1725(20) 0.032(7) Uiso 1 d . . H10W H 0.4156(30) -0.2944(20) 0.1784(21) 0.040(8) Uiso 1 d . . H11 H -0.0801(22) 0.2163(16) 0.2738(18) 0.022(6) Uiso 1 d . . H12 H 0.1548(21) 0.2083(15) 0.2580(16) 0.016(5) Uiso 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 V1 0.0096(2) 0.0147(2) 0.0137(2) 0.00019(12) -0.00060(12) -0.00177(12) K1 0.0160(2) 0.0186(2) 0.0147(2) -0.0001(2) 0.0013(2) -0.0006(2) O1 0.0129(6) 0.0273(7) 0.0221(7) -0.0010(6) 0.0016(5) 0.0001(6) O2 0.0211(7) 0.0182(7) 0.0191(7) 0.0026(6) -0.0018(5) -0.0027(5) O3 0.0236(7) 0.0176(7) 0.0179(7) -0.0007(6) -0.0004(6) -0.0044(6) O4 0.0172(6) 0.0153(6) 0.0141(7) -0.0005(5) -0.0027(5) -0.0017(5) O5 0.0204(7) 0.0163(7) 0.0146(7) -0.0005(5) -0.0029(5) -0.0045(5) O6 0.0216(7) 0.0144(7) 0.0176(7) -0.0001(5) -0.0016(5) -0.0003(5) O7 0.0317(8) 0.0199(7) 0.0156(7) 0.0013(6) -0.0063(6) -0.0050(6) O8 0.0203(8) 0.0303(10) 0.0554(12) -0.0115(9) -0.0087(8) 0.0054(8) O9 0.0208(9) 0.0288(9) 0.0428(10) -0.0112(7) 0.0091(7) -0.0066(7) O10 0.0196(8) 0.0215(8) 0.0265(8) -0.0079(7) -0.0053(6) 0.0056(6) N1 0.0139(8) 0.0140(7) 0.0153(8) 0.0019(6) 0.0002(6) -0.0004(6) N2 0.0127(7) 0.0131(8) 0.0159(8) 0.0001(6) 0.0009(6) -0.0011(6) C1 0.0092(8) 0.0155(9) 0.0163(10) -0.0016(7) -0.0002(7) 0.0025(7) C2 0.0135(9) 0.0174(9) 0.0156(10) -0.0012(8) 0.0008(7) -0.0008(7) C3 0.0198(10) 0.0205(10) 0.0212(10) 0.0015(8) 0.0043(8) -0.0004(8) C4 0.0333(12) 0.0210(10) 0.0170(10) -0.0002(8) 0.0069(9) 0.0002(9) C5 0.0331(12) 0.0201(10) 0.0151(10) 0.0012(8) -0.0057(9) -0.0033(9) C6 0.0184(10) 0.0164(9) 0.0232(11) 0.0018(8) -0.0056(8) -0.0012(8) C7 0.0144(9) 0.0106(8) 0.0165(10) 0.0040(7) -0.0013(7) -0.0001(7) C8 0.0133(9) 0.0109(9) 0.0180(10) 0.0030(7) -0.0010(7) -0.0006(7) C9 0.0120(9) 0.0170(10) 0.0258(11) 0.0028(8) -0.0033(8) -0.0014(8) C10 0.0113(10) 0.0181(10) 0.0373(12) 0.0047(9) 0.0059(9) -0.0002(8) C11 0.0210(10) 0.0195(10) 0.0289(12) -0.0003(9) 0.0118(9) 0.0006(8) C12 0.0169(10) 0.0185(10) 0.0187(10) -0.0009(8) 0.0019(8) -0.0023(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 V1 O1 1.6030(13) . ? V1 O3 1.8648(13) . ? V1 O2 1.8989(13) . ? V1 O5 2.0272(13) . ? V1 O4 2.0663(13) . ? V1 N1 2.129(2) . ? V1 N2 2.2583(15) . ? V1 K1 3.6859(5) . ? K1 O3 2.6998(14) . ? K1 O7 2.7371(14) 4_565 ? K1 O7 2.7433(14) 2_655 ? K1 O6 2.7521(13) 2_655 ? K1 O2 2.7523(13) . ? K1 O9 2.777(2) 3_665 ? K1 O10 2.818(2) 3_655 ? K1 O1 3.2679(14) . ? K1 C2 3.490(2) 2_655 ? K1 C1 3.506(2) 2_655 ? K1 K1 4.5342(8) 3_665 ? O2 O3 1.437(2) . ? O4 C1 1.273(2) . ? O5 C2 1.288(2) . ? O6 C1 1.230(2) . ? O6 K1 2.7521(13) 2_645 ? O7 C2 1.219(2) . ? O7 K1 2.7371(14) 4_566 ? O7 K1 2.7433(14) 2_645 ? O9 K1 2.777(2) 3_665 ? O10 K1 2.818(2) 3_655 ? N1 C3 1.343(2) . ? N1 C7 1.359(2) . ? N2 C12 1.335(2) . ? N2 C8 1.347(2) . ? C1 C2 1.543(2) . ? C1 K1 3.506(2) 2_645 ? C2 K1 3.490(2) 2_645 ? C3 C4 1.379(3) . ? C4 C5 1.380(3) . ? C5 C6 1.383(3) . ? C6 C7 1.381(3) . ? C7 C8 1.485(3) . ? C8 C9 1.392(3) . ? C9 C10 1.382(3) . ? C10 C11 1.377(3) . ? C11 C12 1.385(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 O1 V1 O3 103.95(6) . . ? O1 V1 O2 99.74(7) . . ? O3 V1 O2 44.87(6) . . ? O1 V1 O5 98.62(6) . . ? O3 V1 O5 77.61(5) . . ? O2 V1 O5 122.24(6) . . ? O1 V1 O4 94.50(6) . . ? O3 V1 O4 150.66(6) . . ? O2 V1 O4 153.27(5) . . ? O5 V1 O4 77.21(5) . . ? O1 V1 N1 93.93(6) . . ? O3 V1 N1 122.79(6) . . ? O2 V1 N1 79.00(6) . . ? O5 V1 N1 152.55(6) . . ? O4 V1 N1 77.55(5) . . ? O1 V1 N2 166.61(6) . . ? O3 V1 N2 87.61(6) . . ? O2 V1 N2 83.59(6) . . ? O5 V1 N2 90.36(6) . . ? O4 V1 N2 77.74(5) . . ? N1 V1 N2 73.86(6) . . ? O1 V1 K1 62.39(5) . . ? O3 V1 K1 44.68(4) . . ? O2 V1 K1 46.61(4) . . ? O5 V1 K1 99.44(4) . . ? O4 V1 K1 156.17(4) . . ? N1 V1 K1 108.01(4) . . ? N2 V1 K1 126.06(4) . . ? O3 K1 O7 102.79(4) . 4_565 ? O3 K1 O7 90.72(4) . 2_655 ? O7 K1 O7 68.35(5) 4_565 2_655 ? O3 K1 O6 80.33(4) . 2_655 ? O7 K1 O6 129.65(4) 4_565 2_655 ? O7 K1 O6 61.34(4) 2_655 2_655 ? O3 K1 O2 30.53(4) . . ? O7 K1 O2 79.94(4) 4_565 . ? O7 K1 O2 100.85(4) 2_655 . ? O6 K1 O2 110.50(4) 2_655 . ? O3 K1 O9 169.45(5) . 3_665 ? O7 K1 O9 87.46(5) 4_565 3_665 ? O7 K1 O9 95.48(5) 2_655 3_665 ? O6 K1 O9 95.16(5) 2_655 3_665 ? O2 K1 O9 153.91(5) . 3_665 ? O3 K1 O10 120.36(4) . 3_655 ? O7 K1 O10 73.95(4) 4_565 3_655 ? O7 K1 O10 135.60(5) 2_655 3_655 ? O6 K1 O10 147.15(4) 2_655 3_655 ? O2 K1 O10 94.68(4) . 3_655 ? O9 K1 O10 59.71(5) 3_665 3_655 ? O3 K1 O1 53.57(4) . . ? O7 K1 O1 119.94(4) 4_565 . ? O7 K1 O1 143.87(4) 2_655 . ? O6 K1 O1 102.40(4) 2_655 . ? O2 K1 O1 52.10(4) . . ? O9 K1 O1 119.03(4) 3_665 . ? O10 K1 O1 76.26(4) 3_655 . ? O3 K1 C2 88.37(4) . 2_655 ? O7 K1 C2 86.19(4) 4_565 2_655 ? O7 K1 C2 17.93(4) 2_655 2_655 ? O6 K1 C2 43.47(4) 2_655 2_655 ? O2 K1 C2 106.84(4) . 2_655 ? O9 K1 C2 94.91(5) 3_665 2_655 ? O10 K1 C2 147.70(5) 3_655 2_655 ? O1 K1 C2 136.03(4) . 2_655 ? O3 K1 C1 82.42(4) . 2_655 ? O7 K1 C1 111.66(4) 4_565 2_655 ? O7 K1 C1 43.33(4) 2_655 2_655 ? O6 K1 C1 18.01(4) 2_655 2_655 ? O2 K1 C1 109.60(4) . 2_655 ? O9 K1 C1 96.25(5) 3_665 2_655 ? O10 K1 C1 155.61(4) 3_655 2_655 ? O1 K1 C1 116.73(4) . 2_655 ? C2 K1 C1 25.49(4) 2_655 2_655 ? O3 K1 V1 29.06(3) . . ? O7 K1 V1 108.63(3) 4_565 . ? O7 K1 V1 119.56(3) 2_655 . ? O6 K1 V1 97.69(3) 2_655 . ? O2 K1 V1 30.09(3) . . ? O9 K1 V1 144.65(4) 3_665 . ? O10 K1 V1 93.87(3) 3_655 . ? O1 K1 V1 25.76(2) . . ? C2 K1 V1 116.83(3) 2_655 . ? C1 K1 V1 105.91(3) 2_655 . ? O3 K1 K1 98.12(3) . 3_665 ? O7 K1 K1 34.22(3) 4_565 3_665 ? O7 K1 K1 34.13(3) 2_655 3_665 ? O6 K1 K1 95.46(3) 2_655 3_665 ? O2 K1 K1 90.48(3) . 3_665 ? O9 K1 K1 91.78(4) 3_665 3_665 ? O10 K1 K1 105.39(4) 3_655 3_665 ? O1 K1 K1 142.18(3) . 3_665 ? C2 K1 K1 51.99(3) 2_655 3_665 ? C1 K1 K1 77.45(3) 2_655 3_665 ? V1 K1 K1 119.425(15) . 3_665 ? V1 O1 K1 91.85(6) . . ? O3 O2 V1 66.31(7) . . ? O3 O2 K1 72.71(7) . . ? V1 O2 K1 103.30(5) . . ? O2 O3 V1 68.82(7) . . ? O2 O3 K1 76.76(8) . . ? V1 O3 K1 106.27(6) . . ? C1 O4 V1 117.51(11) . . ? C2 O5 V1 118.10(11) . . ? C1 O6 K1 118.21(11) . 2_645 ? C2 O7 K1 129.77(12) . 4_566 ? C2 O7 K1 118.25(12) . 2_645 ? K1 O7 K1 111.65(5) 4_566 2_645 ? C3 N1 C7 118.8(2) . . ? C3 N1 V1 121.45(13) . . ? C7 N1 V1 119.73(12) . . ? C12 N2 C8 119.2(2) . . ? C12 N2 V1 124.85(12) . . ? C8 N2 V1 115.95(12) . . ? O6 C1 O4 126.4(2) . . ? O6 C1 C2 120.3(2) . . ? O4 C1 C2 113.3(2) . . ? O6 C1 K1 43.77(9) . 2_645 ? O4 C1 K1 169.40(12) . 2_645 ? C2 C1 K1 76.69(10) . 2_645 ? O7 C2 O5 125.7(2) . . ? O7 C2 C1 121.3(2) . . ? O5 C2 C1 112.9(2) . . ? O7 C2 K1 43.83(9) . 2_645 ? O5 C2 K1 168.30(12) . 2_645 ? C1 C2 K1 77.83(10) . 2_645 ? N1 C3 C4 122.4(2) . . ? C3 C4 C5 119.0(2) . . ? C4 C5 C6 118.9(2) . . ? C7 C6 C5 119.8(2) . . ? N1 C7 C6 121.1(2) . . ? N1 C7 C8 115.4(2) . . ? C6 C7 C8 123.5(2) . . ? N2 C8 C9 121.4(2) . . ? N2 C8 C7 115.0(2) . . ? C9 C8 C7 123.6(2) . . ? C10 C9 C8 118.8(2) . . ? C11 C10 C9 119.6(2) . . ? C10 C11 C12 118.7(2) . . ? N2 C12 C11 122.3(2) . . ? _refine_diff_density_max 0.275 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.051