Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Michal Sivak' _publ_contact_author_address ; Inorganic Chemistry Comenius University, Faculty of Natural Sciences Mlynska dolina Bratislava 84215 SLOVAKIA ; _publ_contact_author_email SIVAK@FNS.UNIBA.SK _publ_section_title ; New interpretation of the multiple vanadium-oxygen bonds in the central VO(?2-O2)+ group. Synthesis, structure, supramolecular interactions and DFT studies for complexes with 2,2'-bipyridine, 1,10-phenanthroline, pyrazinato(1-) and pyrazinamide ligands ; loop_ _publ_author_name 'Michal Sivak' 'Robert Gyepes' 'Silvia Pacigova' 'Jozef Tatiersky' data_voo2pcabpy _database_code_depnum_ccdc_archive 'CCDC 602891' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H11 N4 O5 V' _chemical_formula_sum 'C15 H11 N4 O5 V' _chemical_formula_weight 378.22 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' V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' 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 7.5040(3) _cell_length_b 8.4130(5) _cell_length_c 23.3830(11) _cell_angle_alpha 90.00 _cell_angle_beta 101.281(3) _cell_angle_gamma 90.00 _cell_volume 1447.67(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description fragment _exptl_crystal_colour orange _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.735 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.724 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\w and \p scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9622 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0529 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 29.12 _reflns_number_total 3813 _reflns_number_gt 2729 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2001)' _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^)+(0.0316P)^2^+1.4660P] 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 3813 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0770 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1036 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 V V 0.39920(5) 0.81889(5) 0.149024(17) 0.02208(12) Uani 1 1 d . . . N1 N 0.4802(2) 1.0572(2) 0.11709(8) 0.0209(4) Uani 1 1 d . . . C2 C 0.5845(3) 1.1673(3) 0.14909(10) 0.0269(5) Uani 1 1 d . . . H2 H 0.6477 1.1388 0.1859 0.032 Uiso 1 1 calc R . . C3 C 0.6024(3) 1.3197(3) 0.13009(11) 0.0282(5) Uani 1 1 d . . . H3 H 0.6768 1.3923 0.1535 0.034 Uiso 1 1 calc R . . C4 C 0.5076(3) 1.3637(3) 0.07540(11) 0.0278(5) Uani 1 1 d . . . H4 H 0.5164 1.4666 0.0617 0.033 Uiso 1 1 calc R . . C5 C 0.4001(3) 1.2521(3) 0.04168(10) 0.0254(5) Uani 1 1 d . . . H5 H 0.3359 1.2788 0.0048 0.030 Uiso 1 1 calc R . . C6 C 0.3889(3) 1.0999(3) 0.06335(10) 0.0212(5) Uani 1 1 d . . . C7 C 0.2784(3) 0.9720(3) 0.03078(10) 0.0205(5) Uani 1 1 d . . . C8 C 0.1986(3) 0.9853(3) -0.02819(10) 0.0250(5) Uani 1 1 d . . . H8 H 0.2106 1.0787 -0.0484 0.030 Uiso 1 1 calc R . . C9 C 0.1017(3) 0.8589(3) -0.05633(11) 0.0282(5) Uani 1 1 d . . . H9 H 0.0477 0.8663 -0.0956 0.034 Uiso 1 1 calc R . . C10 C 0.0859(3) 0.7213(3) -0.02546(11) 0.0309(6) Uani 1 1 d . . . H10 H 0.0236 0.6338 -0.0438 0.037 Uiso 1 1 calc R . . C11 C 0.1647(3) 0.7160(3) 0.03322(11) 0.0275(5) Uani 1 1 d . . . H11 H 0.1516 0.6243 0.0542 0.033 Uiso 1 1 calc R . . N12 N 0.2592(2) 0.8380(2) 0.06088(8) 0.0213(4) Uani 1 1 d . . . C13 C 0.7927(3) 0.7424(3) 0.19051(10) 0.0239(5) Uani 1 1 d . . . C14 C 0.9619(3) 0.7230(3) 0.22607(11) 0.0326(6) Uani 1 1 d . . . H14 H 1.0563 0.6803 0.2105 0.039 Uiso 1 1 calc R . . N15 N 0.9924(3) 0.7646(3) 0.28246(10) 0.0387(6) Uani 1 1 d . . . C16 C 0.8535(4) 0.8281(3) 0.30183(11) 0.0360(6) Uani 1 1 d . . . H16 H 0.8710 0.8597 0.3406 0.043 Uiso 1 1 calc R . . C17 C 0.6828(4) 0.8493(3) 0.26664(10) 0.0306(6) Uani 1 1 d . . . H17 H 0.5894 0.8938 0.2822 0.037 Uiso 1 1 calc R . . N18 N 0.6526(3) 0.8062(2) 0.21076(8) 0.0232(4) Uani 1 1 d . . . C19 C 0.7497(3) 0.7025(3) 0.12674(10) 0.0242(5) Uani 1 1 d . . . O20 O 0.8612(2) 0.6375(2) 0.10268(7) 0.0315(4) Uani 1 1 d . . . O21 O 0.5888(2) 0.7466(2) 0.10159(7) 0.0231(3) Uani 1 1 d . . . O22 O 0.3348(2) 0.6400(2) 0.15756(8) 0.0305(4) Uani 1 1 d . . . O23 O 0.3357(2) 0.9302(2) 0.21091(7) 0.0332(4) Uani 1 1 d . . . O24 O 0.1964(2) 0.9383(2) 0.16017(7) 0.0316(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 V 0.0226(2) 0.0219(2) 0.0212(2) 0.00258(17) 0.00313(14) -0.00079(17) N1 0.0212(9) 0.0201(10) 0.0208(9) 0.0008(8) 0.0030(7) -0.0014(8) C2 0.0261(11) 0.0271(14) 0.0255(12) 0.0005(10) 0.0001(9) -0.0009(11) C3 0.0290(12) 0.0232(13) 0.0309(13) -0.0032(11) 0.0017(10) -0.0033(11) C4 0.0317(12) 0.0209(13) 0.0309(13) 0.0014(10) 0.0063(10) -0.0025(10) C5 0.0274(11) 0.0235(13) 0.0243(12) 0.0033(10) 0.0027(9) -0.0002(10) C6 0.0194(10) 0.0218(12) 0.0225(11) 0.0000(9) 0.0041(8) -0.0001(9) C7 0.0162(10) 0.0211(12) 0.0242(11) 0.0013(9) 0.0041(8) 0.0019(9) C8 0.0263(11) 0.0248(13) 0.0235(12) 0.0026(10) 0.0036(9) 0.0013(10) C9 0.0260(12) 0.0333(15) 0.0237(12) -0.0037(10) 0.0013(9) -0.0008(11) C10 0.0269(12) 0.0309(15) 0.0328(13) -0.0062(11) 0.0006(10) -0.0076(11) C11 0.0251(11) 0.0233(13) 0.0330(13) 0.0008(10) 0.0029(10) -0.0045(10) N12 0.0208(9) 0.0193(10) 0.0231(9) 0.0017(8) 0.0026(7) -0.0012(8) C13 0.0275(12) 0.0191(12) 0.0249(12) 0.0037(10) 0.0047(9) -0.0009(10) C14 0.0284(12) 0.0343(15) 0.0332(14) 0.0014(11) 0.0015(10) 0.0022(11) N15 0.0364(12) 0.0424(15) 0.0318(12) -0.0002(11) -0.0069(10) 0.0027(11) C16 0.0446(15) 0.0374(16) 0.0221(12) -0.0025(11) -0.0031(11) 0.0069(13) C17 0.0387(13) 0.0291(15) 0.0235(12) -0.0019(10) 0.0050(10) 0.0035(12) N18 0.0280(10) 0.0219(11) 0.0185(9) 0.0016(8) 0.0016(7) -0.0009(9) C19 0.0274(11) 0.0191(12) 0.0261(12) 0.0029(10) 0.0056(9) -0.0028(10) O20 0.0283(9) 0.0370(11) 0.0311(9) -0.0033(8) 0.0101(7) 0.0023(8) O21 0.0250(8) 0.0228(9) 0.0210(8) 0.0009(7) 0.0031(6) 0.0009(7) O22 0.0328(9) 0.0257(10) 0.0336(10) 0.0071(8) 0.0078(7) -0.0015(8) O23 0.0319(9) 0.0380(11) 0.0297(9) 0.0006(8) 0.0059(7) 0.0070(8) O24 0.0277(9) 0.0366(11) 0.0302(9) 0.0012(8) 0.0046(7) 0.0058(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 V O22 1.6048(18) . ? V O23 1.8621(18) . ? V O24 1.8838(17) . ? V O21 2.0596(16) . ? V N12 2.1284(19) . ? V N18 2.1533(18) . ? V N1 2.264(2) . ? N1 C2 1.342(3) . ? N1 C6 1.356(3) . ? C2 C3 1.373(4) . ? C2 H2 0.9300 . ? C3 C4 1.386(3) . ? C3 H3 0.9300 . ? C4 C5 1.381(3) . ? C4 H4 0.9300 . ? C5 C6 1.386(3) . ? C5 H5 0.9300 . ? C6 C7 1.476(3) . ? C7 N12 1.352(3) . ? C7 C8 1.396(3) . ? C8 C9 1.380(3) . ? C8 H8 0.9300 . ? C9 C10 1.382(4) . ? C9 H9 0.9300 . ? C10 C11 1.385(3) . ? C10 H10 0.9300 . ? C11 N12 1.340(3) . ? C11 H11 0.9300 . ? C13 N18 1.346(3) . ? C13 C14 1.384(3) . ? C13 C19 1.501(3) . ? C14 N15 1.340(3) . ? C14 H14 0.9300 . ? N15 C16 1.327(4) . ? C16 C17 1.392(3) . ? C16 H16 0.9300 . ? C17 N18 1.332(3) . ? C17 H17 0.9300 . ? C19 O20 1.225(3) . ? C19 O21 1.290(3) . ? O23 O24 1.421(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 O22 V O23 104.23(9) . . ? O22 V O24 102.22(9) . . ? O23 V O24 44.58(7) . . ? O22 V O21 92.67(8) . . ? O23 V O21 151.14(7) . . ? O24 V O21 153.37(7) . . ? O22 V N12 95.03(8) . . ? O23 V N12 124.17(8) . . ? O24 V N12 80.48(7) . . ? O21 V N12 76.28(7) . . ? O22 V N18 96.78(8) . . ? O23 V N18 80.25(8) . . ? O24 V N18 124.40(8) . . ? O21 V N18 74.57(7) . . ? N12 V N18 148.95(8) . . ? O22 V N1 168.05(8) . . ? O23 V N1 86.38(8) . . ? O24 V N1 81.34(8) . . ? O21 V N1 79.97(7) . . ? N12 V N1 74.17(7) . . ? N18 V N1 90.36(7) . . ? C2 N1 C6 117.9(2) . . ? C2 N1 V 126.31(15) . . ? C6 N1 V 114.86(15) . . ? N1 C2 C3 123.2(2) . . ? N1 C2 H2 118.4 . . ? C3 C2 H2 118.4 . . ? C2 C3 C4 118.9(2) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 118.8(2) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C4 C5 C6 119.4(2) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? N1 C6 C5 121.8(2) . . ? N1 C6 C7 114.6(2) . . ? C5 C6 C7 123.6(2) . . ? N12 C7 C8 120.8(2) . . ? N12 C7 C6 116.46(19) . . ? C8 C7 C6 122.7(2) . . ? C9 C8 C7 119.6(2) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 119.2(2) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? C9 C10 C11 118.7(2) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? N12 C11 C10 122.5(2) . . ? N12 C11 H11 118.8 . . ? C10 C11 H11 118.8 . . ? C11 N12 C7 119.2(2) . . ? C11 N12 V 121.59(16) . . ? C7 N12 V 118.99(15) . . ? N18 C13 C14 121.5(2) . . ? N18 C13 C19 114.1(2) . . ? C14 C13 C19 124.3(2) . . ? N15 C14 C13 121.4(2) . . ? N15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C16 N15 C14 116.5(2) . . ? N15 C16 C17 122.9(2) . . ? N15 C16 H16 118.5 . . ? C17 C16 H16 118.5 . . ? N18 C17 C16 120.4(2) . . ? N18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C17 N18 C13 117.3(2) . . ? C17 N18 V 127.07(17) . . ? C13 N18 V 115.60(15) . . ? O20 C19 O21 125.6(2) . . ? O20 C19 C13 121.5(2) . . ? O21 C19 C13 112.9(2) . . ? C19 O21 V 121.55(15) . . ? O24 O23 V 68.52(10) . . ? O23 O24 V 66.90(10) . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 29.12 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.420 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.074 # Attachment 'Sivak-22.cif' data_voo2pcaphen _database_code_depnum_ccdc_archive 'CCDC 602892' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_sum 'C17 H11 N4 O5 V' _chemical_formula_moiety 'C17 H11 N4 O5 V' _chemical_formula_weight 402.24 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' V V 0.3005 0.5294 '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 Pca21 _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 14.2730(7) _cell_length_b 11.1150(7) _cell_length_c 10.1940(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1617.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 2138 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.652 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.654 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\w and \p scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22161 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1357 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 27.57 _reflns_number_total 3560 _reflns_number_gt 2035 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2001)' _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^)+(0.0194P)^2^+1.8152P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(13) _refine_ls_number_reflns 3560 _refine_ls_number_parameters 245 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1526 _refine_ls_R_factor_gt 0.0635 _refine_ls_wR_factor_ref 0.1056 _refine_ls_wR_factor_gt 0.0839 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 V V 0.41723(6) 0.18896(6) 0.68382(10) 0.0272(2) Uani 1 1 d . . . C2 C 0.4253(4) 0.3137(5) 0.4184(5) 0.0345(13) Uani 1 1 d . . . H2 H 0.4368 0.2364 0.3875 0.041 Uiso 1 1 calc R . . C3 C 0.4221(4) 0.4085(5) 0.3285(6) 0.0425(15) Uani 1 1 d . . . H3 H 0.4291 0.3935 0.2392 0.051 Uiso 1 1 calc R . . C4 C 0.4087(4) 0.5225(5) 0.3721(6) 0.0402(15) Uani 1 1 d . . . H4 H 0.4103 0.5866 0.3135 0.048 Uiso 1 1 calc R . . C5 C 0.3922(4) 0.5436(5) 0.5071(6) 0.0374(16) Uani 1 1 d . . . C6 C 0.3752(4) 0.6595(5) 0.5605(7) 0.0441(16) Uani 1 1 d . . . H6 H 0.3777 0.7263 0.5056 0.053 Uiso 1 1 calc R . . C7 C 0.3558(3) 0.6750(4) 0.6878(9) 0.0442(14) Uani 1 1 d . . . H7 H 0.3424 0.7516 0.7193 0.053 Uiso 1 1 calc R . . C8 C 0.3553(4) 0.5724(5) 0.7779(6) 0.0354(15) Uani 1 1 d . . . C9 C 0.3368(4) 0.5811(5) 0.9131(7) 0.0429(16) Uani 1 1 d . . . H9 H 0.3229 0.6552 0.9505 0.051 Uiso 1 1 calc R . . C10 C 0.3395(4) 0.4807(5) 0.9886(6) 0.0366(15) Uani 1 1 d . . . H10 H 0.3278 0.4859 1.0781 0.044 Uiso 1 1 calc R . . C11 C 0.3600(4) 0.3684(5) 0.9311(6) 0.0339(14) Uani 1 1 d . . . H11 H 0.3606 0.3002 0.9840 0.041 Uiso 1 1 calc R . . C13 C 0.3752(4) 0.4574(5) 0.7298(6) 0.0301(16) Uani 1 1 d . . . C14 C 0.3944(4) 0.4431(5) 0.5896(6) 0.0331(15) Uani 1 1 d . . . C15 C 0.2605(4) 0.0608(4) 0.8089(6) 0.0270(12) Uani 1 1 d . . . C17 C 0.3939(4) 0.0096(5) 0.9185(6) 0.0364(15) Uani 1 1 d . . . H17 H 0.4575 0.0195 0.9347 0.044 Uiso 1 1 calc R . . C18 C 0.3440(4) -0.0733(5) 0.9911(5) 0.0337(15) Uani 1 1 d . . . H18 H 0.3750 -0.1170 1.0556 0.040 Uiso 1 1 calc R . . C20 C 0.2112(4) -0.0245(5) 0.8809(6) 0.0360(15) Uani 1 1 d . . . H20 H 0.1474 -0.0344 0.8653 0.043 Uiso 1 1 calc R . . C21 C 0.2164(4) 0.1418(4) 0.7067(6) 0.0297(14) Uani 1 1 d . . . N1 N 0.4126(3) 0.3298(4) 0.5464(4) 0.0286(12) Uani 1 1 d . . . N12 N 0.3786(3) 0.3565(4) 0.8038(5) 0.0258(11) Uani 1 1 d . . . N16 N 0.3530(3) 0.0760(3) 0.8253(4) 0.0264(10) Uani 1 1 d . . . N19 N 0.2527(4) -0.0930(4) 0.9721(4) 0.0395(13) Uani 1 1 d . . . O22 O 0.1320(2) 0.1433(3) 0.6885(5) 0.0352(8) Uani 1 1 d . . . O23 O 0.2781(2) 0.2072(3) 0.6481(3) 0.0311(10) Uani 1 1 d . . . O24 O 0.5167(2) 0.1691(3) 0.8001(4) 0.0336(9) Uani 1 1 d . . . O25 O 0.5395(2) 0.2527(3) 0.6973(4) 0.0321(8) Uani 1 1 d . . . O26 O 0.4317(3) 0.0852(3) 0.5769(4) 0.0340(9) 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 V 0.0241(4) 0.0253(4) 0.0321(5) -0.0002(6) 0.0000(6) -0.0008(4) C2 0.032(4) 0.041(3) 0.030(3) 0.011(3) 0.003(3) -0.003(3) C3 0.035(4) 0.059(4) 0.033(4) 0.007(3) 0.004(3) -0.001(3) C4 0.027(3) 0.053(4) 0.040(4) 0.026(3) 0.002(3) -0.001(3) C5 0.036(4) 0.033(3) 0.043(4) 0.013(3) -0.002(3) -0.003(3) C6 0.042(4) 0.032(4) 0.058(5) 0.017(3) 0.001(3) 0.002(3) C7 0.033(3) 0.025(3) 0.075(5) -0.001(4) -0.005(5) 0.005(2) C8 0.026(3) 0.035(3) 0.044(4) 0.001(3) -0.002(3) 0.009(3) C9 0.036(4) 0.035(3) 0.057(5) -0.013(3) -0.001(3) 0.009(3) C10 0.031(4) 0.045(4) 0.034(3) -0.009(3) 0.001(3) 0.008(3) C11 0.027(4) 0.038(3) 0.037(4) 0.001(3) 0.003(3) 0.001(3) C13 0.019(3) 0.026(3) 0.046(4) 0.000(3) 0.002(3) 0.002(2) C14 0.019(3) 0.031(4) 0.049(4) 0.005(3) 0.001(3) -0.002(3) C15 0.025(3) 0.019(3) 0.037(3) -0.005(3) 0.000(3) 0.005(2) C17 0.034(4) 0.038(4) 0.037(4) 0.000(3) -0.007(3) 0.000(3) C18 0.038(4) 0.029(3) 0.034(4) 0.001(3) -0.008(3) 0.005(3) C20 0.029(4) 0.031(3) 0.048(4) -0.003(3) -0.002(3) -0.001(3) C21 0.030(3) 0.027(3) 0.032(4) -0.013(3) 0.001(3) 0.004(2) N1 0.023(3) 0.037(3) 0.026(3) 0.001(2) 0.001(2) -0.005(2) N12 0.021(3) 0.028(3) 0.028(3) 0.000(2) -0.002(2) -0.001(2) N16 0.027(3) 0.024(2) 0.028(3) 0.000(2) -0.006(2) 0.001(2) N19 0.037(3) 0.037(3) 0.045(4) 0.001(2) -0.002(3) 0.001(3) O22 0.024(2) 0.0405(19) 0.041(2) -0.003(3) -0.003(3) 0.0031(14) O23 0.023(2) 0.034(2) 0.037(3) 0.0048(16) -0.0036(16) -0.0003(17) O24 0.027(2) 0.0273(18) 0.047(2) 0.002(2) -0.0043(19) -0.0052(16) O25 0.0238(19) 0.0342(18) 0.038(2) 0.001(2) 0.000(2) -0.0044(14) O26 0.031(2) 0.033(2) 0.038(2) -0.0076(18) 0.0023(19) 0.0017(17) _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 V O26 1.600(4) . ? V O24 1.863(3) . ? V O25 1.889(3) . ? V O23 2.029(3) . ? V N1 2.101(4) . ? V N16 2.121(4) . ? V N12 2.295(5) . ? C2 N1 1.330(7) . ? C2 C3 1.397(7) . ? C2 H2 0.9300 . ? C3 C4 1.357(8) . ? C3 H3 0.9300 . ? C4 C5 1.416(8) . ? C4 H4 0.9300 . ? C5 C14 1.399(7) . ? C5 C6 1.420(8) . ? C6 C7 1.339(10) . ? C6 H6 0.9300 . ? C7 C8 1.464(8) . ? C7 H7 0.9300 . ? C8 C13 1.399(8) . ? C8 C9 1.406(9) . ? C9 C10 1.356(8) . ? C9 H9 0.9300 . ? C10 C11 1.409(7) . ? C10 H10 0.9300 . ? C11 N12 1.331(7) . ? C11 H11 0.9300 . ? C13 N12 1.352(7) . ? C13 C14 1.463(8) . ? C14 N1 1.359(7) . ? C15 N16 1.342(6) . ? C15 C20 1.390(7) . ? C15 C21 1.515(7) . ? C17 N16 1.337(7) . ? C17 C18 1.380(8) . ? C17 H17 0.9300 . ? C18 N19 1.334(7) . ? C18 H18 0.9300 . ? C20 N19 1.340(7) . ? C20 H20 0.9300 . ? C21 O22 1.219(6) . ? C21 O23 1.289(6) . ? O24 O25 1.438(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 O26 V O24 104.46(18) . . ? O26 V O25 101.60(17) . . ? O24 V O25 45.07(15) . . ? O26 V O23 94.34(16) . . ? O24 V O23 150.70(15) . . ? O25 V O23 151.64(14) . . ? O26 V N1 95.00(18) . . ? O24 V N1 122.45(17) . . ? O25 V N1 78.37(17) . . ? O23 V N1 76.99(16) . . ? O26 V N16 95.29(17) . . ? O24 V N16 80.01(16) . . ? O25 V N16 124.89(18) . . ? O23 V N16 76.00(15) . . ? N1 V N16 151.71(18) . . ? O26 V N12 168.16(18) . . ? O24 V N12 86.58(15) . . ? O25 V N12 83.05(15) . . ? O23 V N12 77.25(14) . . ? N1 V N12 75.13(16) . . ? N16 V N12 90.78(16) . . ? N1 C2 C3 122.6(6) . . ? N1 C2 H2 118.7 . . ? C3 C2 H2 118.7 . . ? C4 C3 C2 119.6(6) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 119.8(5) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C14 C5 C4 116.7(5) . . ? C14 C5 C6 119.9(6) . . ? C4 C5 C6 123.4(5) . . ? C7 C6 C5 121.6(5) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C6 C7 C8 120.6(5) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C13 C8 C9 116.4(5) . . ? C13 C8 C7 119.4(6) . . ? C9 C8 C7 124.2(6) . . ? C10 C9 C8 119.6(6) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C9 C10 C11 119.9(6) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? N12 C11 C10 122.3(5) . . ? N12 C11 H11 118.8 . . ? C10 C11 H11 118.8 . . ? N12 C13 C8 124.7(5) . . ? N12 C13 C14 116.6(6) . . ? C8 C13 C14 118.7(5) . . ? N1 C14 C5 123.3(6) . . ? N1 C14 C13 116.9(6) . . ? C5 C14 C13 119.8(6) . . ? N16 C15 C20 121.2(5) . . ? N16 C15 C21 114.8(5) . . ? C20 C15 C21 124.0(5) . . ? N16 C17 C18 121.6(5) . . ? N16 C17 H17 119.2 . . ? C18 C17 H17 119.2 . . ? N19 C18 C17 122.4(5) . . ? N19 C18 H18 118.8 . . ? C17 C18 H18 118.8 . . ? N19 C20 C15 121.9(6) . . ? N19 C20 H20 119.0 . . ? C15 C20 H20 119.0 . . ? O22 C21 O23 126.6(5) . . ? O22 C21 C15 121.6(5) . . ? O23 C21 C15 111.8(5) . . ? C2 N1 C14 117.9(5) . . ? C2 N1 V 123.4(4) . . ? C14 N1 V 118.7(4) . . ? C11 N12 C13 117.0(5) . . ? C11 N12 V 130.4(4) . . ? C13 N12 V 112.6(4) . . ? C17 N16 C15 116.6(5) . . ? C17 N16 V 128.4(4) . . ? C15 N16 V 114.6(3) . . ? C18 N19 C20 116.1(5) . . ? C21 O23 V 121.9(3) . . ? O25 O24 V 68.40(19) . . ? O24 O25 V 66.53(18) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.317 _refine_diff_density_min -0.429 _refine_diff_density_rms 0.085 # Attachment 'Sivak-33.cif' data_voo2picpcaa _database_code_depnum_ccdc_archive 'CCDC 602893' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H13 N4 O8 V' _chemical_formula_weight 380.19 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' O O 0.0106 0.0060 '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' V V 0.3005 0.5294 '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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0160(6) _cell_length_b 14.3350(15) _cell_length_c 15.2690(12) _cell_angle_alpha 84.769(5) _cell_angle_beta 90.185(6) _cell_angle_gamma 83.266(5) _cell_volume 1518.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4750 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 24.11 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.663 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.704 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\w and \p scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21989 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1140 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 24.20 _reflns_number_total 4835 _reflns_number_gt 2968 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2001)' _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^)+(0.0521P)^2^+21.5522P] 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 4835 _refine_ls_number_parameters 435 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1584 _refine_ls_R_factor_gt 0.0977 _refine_ls_wR_factor_ref 0.2584 _refine_ls_wR_factor_gt 0.2332 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _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 V1 V 0.1889(3) 0.59246(13) 0.09011(12) 0.0294(5) Uani 1 1 d . . . N1 N 0.1435(12) 0.4465(6) 0.1253(5) 0.031(2) Uani 1 1 d . . . C2 C -0.0244(14) 0.4311(8) 0.1649(7) 0.033(3) Uani 1 1 d . . . H2 H -0.1050 0.4819 0.1829 0.039 Uiso 1 1 calc R . . C3 C -0.0771(15) 0.3409(8) 0.1788(7) 0.031(3) Uani 1 1 d . . . N4 N 0.0365(13) 0.2657(7) 0.1549(6) 0.040(2) Uani 1 1 d . . . C5 C 0.2060(15) 0.2806(8) 0.1199(7) 0.034(3) Uani 1 1 d . . . H5 H 0.2922 0.2295 0.1069 0.041 Uiso 1 1 calc R . . C6 C 0.2553(15) 0.3727(8) 0.1026(7) 0.031(3) Uani 1 1 d . . . H6 H 0.3699 0.3816 0.0744 0.038 Uiso 1 1 calc R . . C7 C -0.2660(16) 0.3272(9) 0.2189(7) 0.037(3) Uani 1 1 d . . . N8 N -0.3118(13) 0.2401(7) 0.2217(6) 0.042(2) Uani 1 1 d . . . H8A H -0.4197 0.2272 0.2433 0.051 Uiso 1 1 calc R . . H8B H -0.2337 0.1964 0.2019 0.051 Uiso 1 1 calc R . . O9 O -0.3700(11) 0.3937(6) 0.2459(5) 0.0402(19) Uani 1 1 d . . . N10 N 0.2207(12) 0.7335(6) 0.1176(5) 0.029(2) Uani 1 1 d . . . C11 C 0.2215(14) 0.7464(8) 0.2049(7) 0.031(3) Uani 1 1 d . . . C12 C 0.2339(15) 0.8330(8) 0.2352(7) 0.036(3) Uani 1 1 d . . . H12 H 0.2392 0.8392 0.2953 0.044 Uiso 1 1 calc R . . C13 C 0.2384(16) 0.9115(8) 0.1741(8) 0.041(3) Uani 1 1 d . . . H13 H 0.2443 0.9710 0.1928 0.049 Uiso 1 1 calc R . . C14 C 0.2338(15) 0.8986(8) 0.0836(7) 0.036(3) Uani 1 1 d . . . H14 H 0.2338 0.9494 0.0411 0.043 Uiso 1 1 calc R . . C15 C 0.2293(15) 0.8073(9) 0.0602(8) 0.040(3) Uani 1 1 d . . . H15 H 0.2326 0.7978 0.0007 0.048 Uiso 1 1 calc R . . C16 C 0.2019(15) 0.6579(8) 0.2634(7) 0.035(3) Uani 1 1 d . . . O17 O 0.1727(10) 0.5865(5) 0.2213(5) 0.0356(18) Uani 1 1 d . . . O18 O 0.2113(13) 0.6583(6) 0.3439(5) 0.053(2) Uani 1 1 d . . . O19 O 0.3090(10) 0.6351(5) -0.0126(5) 0.0337(18) Uani 1 1 d . . . O20 O 0.2766(10) 0.5375(5) -0.0114(4) 0.0312(17) Uani 1 1 d . . . O21 O 0.4962(10) 0.5479(5) 0.1357(5) 0.0319(17) Uani 1 1 d . . . O22 O -0.0338(10) 0.6197(5) 0.0663(5) 0.0370(19) Uani 1 1 d . . . V2 V 0.8031(3) -0.03457(13) 0.38026(12) 0.0304(5) Uani 1 1 d . . . N31 N 0.8516(12) 0.1067(6) 0.4061(6) 0.032(2) Uani 1 1 d . . . C32 C 1.0108(15) 0.1390(8) 0.3725(7) 0.034(3) Uani 1 1 d . . . H32 H 1.0911 0.1014 0.3382 0.041 Uiso 1 1 calc R . . C33 C 1.0574(16) 0.2274(8) 0.3883(7) 0.034(3) Uani 1 1 d . . . N34 N 0.9453(14) 0.2864(7) 0.4340(7) 0.043(3) Uani 1 1 d . . . C35 C 0.7829(17) 0.2513(8) 0.4662(8) 0.041(3) Uani 1 1 d . . . H35 H 0.7004 0.2896 0.4990 0.049 Uiso 1 1 calc R . . C36 C 0.7351(16) 0.1655(8) 0.4536(7) 0.034(3) Uani 1 1 d . . . H36 H 0.6225 0.1462 0.4772 0.041 Uiso 1 1 calc R . . C37 C 1.2367(16) 0.2587(9) 0.3510(7) 0.035(3) Uani 1 1 d . . . N38 N 1.2638(15) 0.3481(7) 0.3557(7) 0.051(3) Uani 1 1 d . . . H38A H 1.3636 0.3693 0.3326 0.061 Uiso 1 1 calc R . . H38B H 1.1816 0.3849 0.3819 0.061 Uiso 1 1 calc R . . O39 O 1.3503(11) 0.2028(6) 0.3142(5) 0.042(2) Uani 1 1 d . . . N40 N 0.7513(13) -0.1385(7) 0.2954(6) 0.039(2) Uani 1 1 d . . . C41 C 0.7409(15) -0.1097(8) 0.2088(7) 0.034(3) Uani 1 1 d . . . C42 C 0.7108(16) -0.1669(9) 0.1458(8) 0.043(3) Uani 1 1 d . . . H42 H 0.7023 -0.1433 0.0870 0.052 Uiso 1 1 calc R . . C43 C 0.6928(15) -0.2603(9) 0.1695(9) 0.048(3) Uani 1 1 d . . . H43 H 0.6711 -0.3009 0.1273 0.058 Uiso 1 1 calc R . . C44 C 0.7077(16) -0.2925(9) 0.2576(9) 0.049(3) Uani 1 1 d . . . H44 H 0.6994 -0.3556 0.2755 0.059 Uiso 1 1 calc R . . C45 C 0.7353(16) -0.2295(8) 0.3192(8) 0.039(3) Uani 1 1 d . . . H45 H 0.7429 -0.2512 0.3786 0.046 Uiso 1 1 calc R . . C46 C 0.7631(17) -0.0069(8) 0.1899(8) 0.040(3) Uani 1 1 d . . . O47 O 0.8062(10) 0.0345(5) 0.2602(5) 0.0355(18) Uani 1 1 d . . . O48 O 0.7412(14) 0.0338(6) 0.1167(5) 0.057(3) Uani 1 1 d . . . O49 O 0.6922(10) -0.1185(5) 0.4611(5) 0.0335(18) Uani 1 1 d . . . O50 O 0.7300(10) -0.0325(5) 0.4977(5) 0.0358(18) Uani 1 1 d . . . O51 O 1.0255(10) -0.0699(5) 0.3893(5) 0.0342(18) Uani 1 1 d . . . O52 O 0.4888(10) 0.0175(5) 0.3514(5) 0.0361(18) Uani 1 1 d . . . O100 O 0.662(7) 0.508(3) 0.391(3) 0.086(13) Uiso 0.257(4) 1 d P . . O101 O 0.547(6) 0.526(3) 0.440(3) 0.24(2) Uiso 0.65(3) 1 d P . . O102 O 0.982(3) 0.5156(14) 0.4073(13) 0.094(10) Uiso 0.60(3) 1 d P . . O103 O 0.152(4) 0.500(2) 0.4495(19) 0.113(14) Uiso 0.49(3) 1 d P . . 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 0.0277(10) 0.0322(11) 0.0298(10) -0.0028(8) 0.0032(8) -0.0097(8) N1 0.022(5) 0.042(6) 0.028(5) -0.007(4) -0.004(4) -0.007(4) C2 0.022(6) 0.038(7) 0.039(6) -0.001(5) 0.013(5) -0.011(5) C3 0.031(6) 0.032(7) 0.032(6) -0.003(5) 0.005(5) -0.011(5) N4 0.036(6) 0.041(6) 0.044(6) 0.006(5) 0.004(5) -0.020(5) C5 0.029(6) 0.033(7) 0.042(7) 0.006(5) 0.001(5) -0.017(5) C6 0.027(6) 0.041(7) 0.028(6) -0.004(5) 0.000(5) -0.011(5) C7 0.029(6) 0.054(8) 0.032(6) -0.001(6) -0.005(5) -0.022(6) N8 0.024(5) 0.040(6) 0.061(7) 0.003(5) 0.005(5) -0.008(4) O9 0.036(5) 0.041(5) 0.041(5) 0.005(4) 0.009(4) -0.004(4) N10 0.024(5) 0.033(5) 0.029(5) -0.002(4) -0.001(4) -0.005(4) C11 0.019(5) 0.046(7) 0.030(6) -0.006(5) 0.001(5) -0.013(5) C12 0.035(6) 0.047(8) 0.030(6) -0.006(6) 0.010(5) -0.012(6) C13 0.036(7) 0.031(7) 0.057(8) -0.013(6) -0.001(6) -0.006(5) C14 0.039(7) 0.032(7) 0.036(7) 0.001(5) -0.008(5) -0.002(5) C15 0.033(7) 0.053(8) 0.035(7) -0.001(6) 0.007(5) -0.012(6) C16 0.032(6) 0.045(8) 0.029(7) 0.000(6) 0.004(5) -0.009(5) O17 0.036(4) 0.036(5) 0.036(4) -0.002(4) 0.007(3) -0.011(4) O18 0.077(6) 0.056(6) 0.030(5) -0.011(4) 0.003(4) -0.016(5) O19 0.033(4) 0.037(5) 0.034(4) -0.004(3) 0.006(3) -0.010(3) O20 0.031(4) 0.035(4) 0.028(4) -0.002(3) 0.003(3) -0.009(3) O21 0.027(4) 0.036(4) 0.033(4) -0.012(3) 0.001(3) 0.001(3) O22 0.025(4) 0.041(5) 0.048(5) -0.011(4) 0.006(3) -0.015(3) V2 0.0272(10) 0.0352(11) 0.0299(10) -0.0003(8) 0.0023(8) -0.0099(8) N31 0.028(5) 0.042(6) 0.028(5) 0.003(4) 0.005(4) -0.016(4) C32 0.028(6) 0.046(7) 0.030(6) -0.001(5) 0.005(5) -0.013(5) C33 0.047(7) 0.023(6) 0.031(6) 0.011(5) -0.004(5) -0.011(5) N34 0.049(6) 0.036(6) 0.046(6) 0.001(5) -0.004(5) -0.016(5) C35 0.043(7) 0.041(8) 0.040(7) -0.003(6) 0.013(6) -0.007(6) C36 0.030(6) 0.045(7) 0.029(6) 0.002(5) -0.002(5) -0.012(5) C37 0.026(6) 0.046(8) 0.035(6) -0.001(6) -0.004(5) -0.016(6) N38 0.059(7) 0.044(7) 0.057(7) -0.011(5) 0.011(5) -0.032(6) O39 0.034(5) 0.040(5) 0.053(5) 0.016(4) 0.003(4) -0.019(4) N40 0.035(5) 0.038(6) 0.047(6) -0.005(5) 0.000(5) -0.012(4) C41 0.029(6) 0.040(7) 0.035(7) -0.006(5) 0.005(5) -0.013(5) C42 0.040(7) 0.056(9) 0.042(7) -0.023(6) 0.009(6) -0.020(6) C43 0.023(6) 0.054(9) 0.071(10) -0.029(7) 0.016(6) -0.004(6) C44 0.028(7) 0.051(8) 0.073(10) -0.024(7) 0.014(7) -0.012(6) C45 0.045(7) 0.036(7) 0.037(7) -0.006(6) 0.005(6) -0.009(6) C46 0.044(7) 0.043(7) 0.037(7) -0.008(6) -0.001(6) -0.017(6) O47 0.031(4) 0.045(5) 0.032(4) 0.004(4) -0.002(3) -0.014(4) O48 0.086(7) 0.061(6) 0.028(5) 0.002(4) -0.002(5) -0.026(5) O49 0.042(4) 0.026(4) 0.034(4) -0.002(3) -0.001(3) -0.008(3) O50 0.034(4) 0.038(5) 0.038(4) -0.003(4) 0.005(3) -0.016(4) O51 0.027(4) 0.043(5) 0.036(4) -0.004(4) 0.005(3) -0.016(3) O52 0.029(4) 0.042(5) 0.038(4) -0.003(4) -0.006(3) -0.008(3) _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 O22 1.598(7) . ? V1 O19 1.871(7) . ? V1 O20 1.875(7) . ? V1 O17 2.001(7) . ? V1 N10 2.139(9) . ? V1 N1 2.172(9) . ? V1 O21 2.264(7) . ? N1 C6 1.315(13) . ? N1 C2 1.358(13) . ? C2 C3 1.385(14) . ? C2 H2 0.9300 . ? C3 N4 1.343(14) . ? C3 C7 1.488(15) . ? N4 C5 1.337(13) . ? C5 C6 1.406(14) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O9 1.233(14) . ? C7 N8 1.322(14) . ? N8 H8A 0.8600 . ? N8 H8B 0.8600 . ? N10 C15 1.319(14) . ? N10 C11 1.362(13) . ? C11 C12 1.376(15) . ? C11 C16 1.503(15) . ? C12 C13 1.398(15) . ? C12 H12 0.9300 . ? C13 C14 1.412(16) . ? C13 H13 0.9300 . ? C14 C15 1.391(16) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 O18 1.231(13) . ? C16 O17 1.293(13) . ? O19 O20 1.441(9) . ? V2 O51 1.585(7) . ? V2 O50 1.869(7) . ? V2 O49 1.880(7) . ? V2 O47 2.004(7) . ? V2 N40 2.123(9) . ? V2 N31 2.163(9) . ? V2 O52 2.272(7) . ? N31 C32 1.344(13) . ? N31 C36 1.363(14) . ? C32 C33 1.386(15) . ? C32 H32 0.9300 . ? C33 N34 1.333(15) . ? C33 C37 1.483(15) . ? N34 C35 1.373(14) . ? C35 C36 1.342(15) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C37 O39 1.236(13) . ? C37 N38 1.326(14) . ? N38 H38A 0.8600 . ? N38 H38B 0.8600 . ? N40 C45 1.341(14) . ? N40 C41 1.348(14) . ? C41 C42 1.350(15) . ? C41 C46 1.501(16) . ? C42 C43 1.376(17) . ? C42 H42 0.9300 . ? C43 C44 1.381(18) . ? C43 H43 0.9300 . ? C44 C45 1.390(16) . ? C44 H44 0.9300 . ? C45 H45 0.9300 . ? C46 O48 1.214(13) . ? C46 O47 1.323(13) . ? O49 O50 1.451(10) . ? O100 O101 1.13(5) . ? O102 O103 1.34(3) 1_655 ? O103 O102 1.34(3) 1_455 ? 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 O22 V1 O19 102.8(4) . . ? O22 V1 O20 100.9(3) . . ? O19 V1 O20 45.3(3) . . ? O22 V1 O17 98.8(3) . . ? O19 V1 O17 148.4(3) . . ? O20 V1 O17 149.7(3) . . ? O22 V1 N10 92.1(3) . . ? O19 V1 N10 79.7(3) . . ? O20 V1 N10 124.9(3) . . ? O17 V1 N10 76.8(3) . . ? O22 V1 N1 90.9(3) . . ? O19 V1 N1 124.3(3) . . ? O20 V1 N1 79.4(3) . . ? O17 V1 N1 77.5(3) . . ? N10 V1 N1 154.3(3) . . ? O22 V1 O21 174.8(3) . . ? O19 V1 O21 82.3(3) . . ? O20 V1 O21 82.5(3) . . ? O17 V1 O21 76.5(3) . . ? N10 V1 O21 89.1(3) . . ? N1 V1 O21 85.9(3) . . ? C6 N1 C2 117.6(9) . . ? C6 N1 V1 125.0(7) . . ? C2 N1 V1 116.9(7) . . ? N1 C2 C3 120.9(10) . . ? N1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? N4 C3 C2 121.4(10) . . ? N4 C3 C7 119.2(10) . . ? C2 C3 C7 119.4(10) . . ? C5 N4 C3 117.6(9) . . ? N4 C5 C6 120.6(11) . . ? N4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? N1 C6 C5 121.7(10) . . ? N1 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? O9 C7 N8 123.9(10) . . ? O9 C7 C3 121.1(10) . . ? N8 C7 C3 114.9(11) . . ? C7 N8 H8A 120.0 . . ? C7 N8 H8B 120.0 . . ? H8A N8 H8B 120.0 . . ? C15 N10 C11 118.5(10) . . ? C15 N10 V1 127.2(8) . . ? C11 N10 V1 114.2(7) . . ? N10 C11 C12 122.5(10) . . ? N10 C11 C16 113.4(9) . . ? C12 C11 C16 124.1(10) . . ? C11 C12 C13 118.8(10) . . ? C11 C12 H12 120.6 . . ? C13 C12 H12 120.6 . . ? C12 C13 C14 118.8(10) . . ? C12 C13 H13 120.6 . . ? C14 C13 H13 120.6 . . ? C15 C14 C13 117.7(10) . . ? C15 C14 H14 121.1 . . ? C13 C14 H14 121.1 . . ? N10 C15 C14 123.6(11) . . ? N10 C15 H15 118.2 . . ? C14 C15 H15 118.2 . . ? O18 C16 O17 125.8(10) . . ? O18 C16 C11 120.1(10) . . ? O17 C16 C11 114.0(9) . . ? C16 O17 V1 121.3(7) . . ? O20 O19 V1 67.5(4) . . ? O19 O20 V1 67.2(4) . . ? O51 V2 O50 102.2(3) . . ? O51 V2 O49 103.3(3) . . ? O50 V2 O49 45.5(3) . . ? O51 V2 O47 97.9(3) . . ? O50 V2 O47 148.0(3) . . ? O49 V2 O47 149.9(3) . . ? O51 V2 N40 93.3(4) . . ? O50 V2 N40 126.2(3) . . ? O49 V2 N40 80.8(3) . . ? O47 V2 N40 76.7(3) . . ? O51 V2 N31 91.4(4) . . ? O50 V2 N31 78.5(3) . . ? O49 V2 N31 123.8(3) . . ? O47 V2 N31 76.2(3) . . ? N40 V2 N31 152.9(4) . . ? O51 V2 O52 173.8(3) . . ? O50 V2 O52 84.0(3) . . ? O49 V2 O52 81.1(3) . . ? O47 V2 O52 76.5(3) . . ? N40 V2 O52 83.1(3) . . ? N31 V2 O52 89.5(3) . . ? C32 N31 C36 117.3(9) . . ? C32 N31 V2 117.0(8) . . ? C36 N31 V2 125.7(7) . . ? N31 C32 C33 121.1(11) . . ? N31 C32 H32 119.4 . . ? C33 C32 H32 119.4 . . ? N34 C33 C32 122.7(10) . . ? N34 C33 C37 118.5(10) . . ? C32 C33 C37 118.8(11) . . ? C33 N34 C35 114.4(10) . . ? C36 C35 N34 124.6(11) . . ? C36 C35 H35 117.7 . . ? N34 C35 H35 117.7 . . ? C35 C36 N31 119.9(10) . . ? C35 C36 H36 120.0 . . ? N31 C36 H36 120.0 . . ? O39 C37 N38 122.6(10) . . ? O39 C37 C33 119.8(10) . . ? N38 C37 C33 117.6(11) . . ? C37 N38 H38A 120.0 . . ? C37 N38 H38B 120.0 . . ? H38A N38 H38B 120.0 . . ? C45 N40 C41 117.5(10) . . ? C45 N40 V2 126.5(8) . . ? C41 N40 V2 115.9(7) . . ? N40 C41 C42 123.6(11) . . ? N40 C41 C46 112.8(10) . . ? C42 C41 C46 123.6(11) . . ? C41 C42 C43 119.4(12) . . ? C41 C42 H42 120.3 . . ? C43 C42 H42 120.3 . . ? C42 C43 C44 118.3(12) . . ? C42 C43 H43 120.8 . . ? C44 C43 H43 120.8 . . ? C43 C44 C45 119.4(12) . . ? C43 C44 H44 120.3 . . ? C45 C44 H44 120.3 . . ? N40 C45 C44 121.7(11) . . ? N40 C45 H45 119.1 . . ? C44 C45 H45 119.1 . . ? O48 C46 O47 123.7(11) . . ? O48 C46 C41 122.4(10) . . ? O47 C46 C41 113.9(10) . . ? C46 O47 V2 120.3(7) . . ? O50 O49 V2 66.8(4) . . ? O49 O50 V2 67.6(4) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 24.20 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.911 _refine_diff_density_min -0.562 _refine_diff_density_rms 0.128