Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Roland Kraemer' 'Patrick Plitt' 'Hans Pritzkow' _publ_contact_author_name 'Prof Roland Kraemer' _publ_contact_author_address ; Anorganisch-Chemisches Institut Ruprecht-Karls Universitat Heidelberg Im Neuenheimer Feld 270 Heidelberg D-69120 GERMANY ; _publ_contact_author_email ROLAND.KRAEMER@URZ.UNI-HEIDELBERG.DE _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Biphenyl derived Schiff base vanadium(V) complexes with pendant OH-groups - structure, characterization and hydrogen peroxide mediated sulfide oxygenation ; data_plitt13 _database_code_depnum_ccdc_archive 'CCDC 233274' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H15 N O2' _chemical_formula_sum 'C19 H15 N O2' _chemical_formula_weight 289.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.1253(3) _cell_length_b 18.8475(8) _cell_length_c 12.1564(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.5900(10) _cell_angle_gamma 90.00 _cell_volume 1403.34(11) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9120 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(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 'CCD area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13347 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 32.02 _reflns_number_total 4775 _reflns_number_gt 4029 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0774P)^2^+0.4005P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4775 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0545 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1324 _refine_ls_wR_factor_gt 0.1220 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.80996(11) 0.09823(4) 0.05337(6) 0.01626(15) Uani 1 1 d . . . O2 O 0.30046(12) 0.03834(4) -0.05872(6) 0.01802(15) Uani 1 1 d . . . N1 N 0.57620(13) 0.14045(4) -0.11416(7) 0.01455(16) Uani 1 1 d . . . C1 C 0.39338(15) 0.12875(5) -0.18313(7) 0.01411(17) Uani 1 1 d . . . C2 C 0.24863(15) 0.07493(5) -0.15128(7) 0.01422(17) Uani 1 1 d . . . C3 C 0.06087(16) 0.06248(5) -0.21414(8) 0.01650(18) Uani 1 1 d . . . C4 C 0.02191(17) 0.10216(5) -0.30894(8) 0.01872(19) Uani 1 1 d . . . C5 C 0.17048(17) 0.15350(6) -0.34276(8) 0.01913(19) Uani 1 1 d . . . C6 C 0.35577(16) 0.16712(5) -0.27949(8) 0.01771(18) Uani 1 1 d . . . C7 C 0.71425(16) 0.19347(5) -0.12054(8) 0.01542(17) Uani 1 1 d . . . C8 C 0.89612(15) 0.20152(5) -0.04914(7) 0.01399(17) Uani 1 1 d . . . C9 C 1.04056(16) 0.25909(5) -0.06894(8) 0.01707(18) Uani 1 1 d . . . C10 C 1.22608(17) 0.26715(5) -0.00630(8) 0.01810(19) Uani 1 1 d . . . C11 C 1.26733(16) 0.21907(5) 0.08090(8) 0.01581(18) Uani 1 1 d . . . C12 C 1.12789(15) 0.16396(5) 0.10639(7) 0.01337(17) Uani 1 1 d . . . C13 C 0.93759(15) 0.15137(5) 0.03829(7) 0.01306(16) Uani 1 1 d . . . C14 C 1.17418(15) 0.11990(5) 0.20495(7) 0.01357(17) Uani 1 1 d . . . C15 C 1.01845(16) 0.11400(5) 0.28820(8) 0.01591(18) Uani 1 1 d . . . C16 C 1.06842(17) 0.07824(5) 0.38548(8) 0.01796(19) Uani 1 1 d . . . C17 C 1.27260(17) 0.04715(5) 0.40091(8) 0.01908(19) Uani 1 1 d . . . C18 C 1.42603(17) 0.05094(6) 0.31754(8) 0.01915(19) Uani 1 1 d . . . C19 C 1.37762(16) 0.08742(5) 0.22024(8) 0.01661(18) Uani 1 1 d . . . H1N H 0.604(3) 0.1107(11) -0.0583(16) 0.047(5) Uiso 1 1 d . . . H2O H 0.233(3) -0.0020(11) -0.0602(14) 0.038(5) Uiso 1 1 d . . . H3 H -0.037(3) 0.0262(8) -0.1904(12) 0.024(4) Uiso 1 1 d . . . H4 H -0.109(3) 0.0918(8) -0.3525(12) 0.023(4) Uiso 1 1 d . . . H5 H 0.149(3) 0.1789(9) -0.4133(13) 0.026(4) Uiso 1 1 d . . . H6 H 0.457(3) 0.2019(8) -0.3049(12) 0.024(4) Uiso 1 1 d . . . H7 H 0.693(2) 0.2293(8) -0.1784(12) 0.022(4) Uiso 1 1 d . . . H9 H 1.004(3) 0.2943(9) -0.1278(13) 0.027(4) Uiso 1 1 d . . . H10 H 1.323(2) 0.3060(8) -0.0214(13) 0.025(4) Uiso 1 1 d . . . H11 H 1.396(3) 0.2263(8) 0.1271(13) 0.026(4) Uiso 1 1 d . . . H15 H 0.875(2) 0.1359(8) 0.2779(12) 0.018(3) Uiso 1 1 d . . . H16 H 0.962(2) 0.0758(8) 0.4430(12) 0.022(3) Uiso 1 1 d . . . H17 H 1.306(3) 0.0227(8) 0.4685(13) 0.027(4) Uiso 1 1 d . . . H18 H 1.571(3) 0.0273(8) 0.3262(13) 0.026(4) Uiso 1 1 d . . . H19 H 1.486(3) 0.0903(8) 0.1622(13) 0.025(4) 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 O1 0.0146(3) 0.0158(3) 0.0184(3) 0.0029(2) -0.0012(2) -0.0030(2) O2 0.0212(3) 0.0149(3) 0.0179(3) 0.0042(2) -0.0038(3) -0.0012(3) N1 0.0133(3) 0.0154(4) 0.0149(3) 0.0017(3) -0.0018(3) 0.0006(3) C1 0.0132(4) 0.0147(4) 0.0144(4) 0.0005(3) -0.0016(3) 0.0011(3) C2 0.0162(4) 0.0125(4) 0.0140(4) 0.0000(3) -0.0005(3) 0.0019(3) C3 0.0161(4) 0.0155(4) 0.0179(4) -0.0017(3) -0.0016(3) -0.0008(3) C4 0.0181(4) 0.0191(4) 0.0188(4) -0.0016(3) -0.0050(3) 0.0008(3) C5 0.0208(4) 0.0204(4) 0.0160(4) 0.0016(3) -0.0044(3) 0.0012(3) C6 0.0182(4) 0.0186(4) 0.0164(4) 0.0033(3) -0.0023(3) -0.0013(3) C7 0.0161(4) 0.0146(4) 0.0155(4) 0.0009(3) -0.0007(3) 0.0007(3) C8 0.0143(4) 0.0132(4) 0.0145(4) 0.0009(3) -0.0006(3) -0.0005(3) C9 0.0205(4) 0.0144(4) 0.0162(4) 0.0023(3) -0.0009(3) -0.0021(3) C10 0.0208(4) 0.0156(4) 0.0179(4) 0.0021(3) -0.0007(3) -0.0053(3) C11 0.0161(4) 0.0160(4) 0.0153(4) -0.0001(3) -0.0004(3) -0.0027(3) C12 0.0139(4) 0.0134(4) 0.0127(4) -0.0005(3) 0.0002(3) -0.0005(3) C13 0.0128(4) 0.0133(4) 0.0131(4) -0.0002(3) 0.0007(3) 0.0002(3) C14 0.0145(4) 0.0137(4) 0.0125(4) -0.0008(3) -0.0007(3) -0.0012(3) C15 0.0157(4) 0.0174(4) 0.0145(4) -0.0008(3) 0.0012(3) 0.0007(3) C16 0.0205(4) 0.0199(4) 0.0135(4) -0.0001(3) 0.0025(3) -0.0004(3) C17 0.0223(5) 0.0199(4) 0.0150(4) 0.0015(3) -0.0027(3) -0.0007(3) C18 0.0172(4) 0.0213(5) 0.0188(4) 0.0017(3) -0.0029(3) 0.0015(3) C19 0.0143(4) 0.0199(4) 0.0157(4) 0.0010(3) 0.0005(3) 0.0004(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 O1 C13 1.2849(11) . ? O2 C2 1.3547(11) . ? O2 H2O 0.86(2) . ? N1 C7 1.3119(12) . ? N1 C1 1.4093(12) . ? N1 H1N 0.89(2) . ? C1 C6 1.3938(13) . ? C1 C2 1.4043(13) . ? C2 C3 1.3941(13) . ? C3 C4 1.3923(14) . ? C3 H3 0.956(15) . ? C4 C5 1.3933(15) . ? C4 H4 0.974(16) . ? C5 C6 1.3884(14) . ? C5 H5 0.990(16) . ? C6 H6 0.958(16) . ? C7 C8 1.4133(13) . ? C7 H7 0.982(15) . ? C8 C9 1.4222(13) . ? C8 C13 1.4429(13) . ? C9 C10 1.3699(14) . ? C9 H9 0.999(16) . ? C10 C11 1.4153(13) . ? C10 H10 0.963(16) . ? C11 C12 1.3820(13) . ? C11 H11 0.972(16) . ? C12 C13 1.4424(12) . ? C12 C14 1.4827(12) . ? C14 C19 1.3990(13) . ? C14 C15 1.4023(13) . ? C15 C16 1.3925(13) . ? C15 H15 0.976(15) . ? C16 C17 1.3921(15) . ? C16 H16 0.963(15) . ? C17 C18 1.3911(15) . ? C17 H17 0.962(16) . ? C18 C19 1.3973(13) . ? C18 H18 0.996(16) . ? C19 H19 0.973(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 C2 O2 H2O 108.8(12) . . ? C7 N1 C1 126.35(8) . . ? C7 N1 H1N 113.9(13) . . ? C1 N1 H1N 119.8(13) . . ? C6 C1 C2 120.47(8) . . ? C6 C1 N1 122.84(9) . . ? C2 C1 N1 116.68(8) . . ? O2 C2 C3 123.68(9) . . ? O2 C2 C1 116.97(8) . . ? C3 C2 C1 119.35(8) . . ? C4 C3 C2 119.78(9) . . ? C4 C3 H3 122.1(9) . . ? C2 C3 H3 118.1(9) . . ? C3 C4 C5 120.69(9) . . ? C3 C4 H4 118.3(9) . . ? C5 C4 H4 120.9(9) . . ? C6 C5 C4 119.85(9) . . ? C6 C5 H5 119.5(9) . . ? C4 C5 H5 120.6(9) . . ? C5 C6 C1 119.78(9) . . ? C5 C6 H6 118.6(9) . . ? C1 C6 H6 121.6(9) . . ? N1 C7 C8 123.37(9) . . ? N1 C7 H7 118.9(9) . . ? C8 C7 H7 117.7(9) . . ? C7 C8 C9 117.76(8) . . ? C7 C8 C13 120.91(8) . . ? C9 C8 C13 121.29(8) . . ? C10 C9 C8 120.30(9) . . ? C10 C9 H9 120.2(9) . . ? C8 C9 H9 119.5(9) . . ? C9 C10 C11 119.08(9) . . ? C9 C10 H10 119.3(9) . . ? C11 C10 H10 121.6(9) . . ? C12 C11 C10 122.90(9) . . ? C12 C11 H11 118.4(9) . . ? C10 C11 H11 118.7(9) . . ? C11 C12 C13 119.51(8) . . ? C11 C12 C14 119.25(8) . . ? C13 C12 C14 121.22(8) . . ? O1 C13 C12 122.39(8) . . ? O1 C13 C8 120.86(8) . . ? C12 C13 C8 116.75(8) . . ? C19 C14 C15 118.75(8) . . ? C19 C14 C12 121.01(8) . . ? C15 C14 C12 120.11(8) . . ? C16 C15 C14 120.40(9) . . ? C16 C15 H15 120.2(8) . . ? C14 C15 H15 119.4(8) . . ? C17 C16 C15 120.50(9) . . ? C17 C16 H16 119.8(9) . . ? C15 C16 H16 119.7(9) . . ? C18 C17 C16 119.53(9) . . ? C18 C17 H17 120.4(10) . . ? C16 C17 H17 120.1(10) . . ? C17 C18 C19 120.20(9) . . ? C17 C18 H18 120.4(9) . . ? C19 C18 H18 119.4(9) . . ? C18 C19 C14 120.58(9) . . ? C18 C19 H19 120.1(9) . . ? C14 C19 H19 119.3(9) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 32.02 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.579 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.064 #===END data_plitt07 _database_code_depnum_ccdc_archive 'CCDC 233275' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H19 N2 O4 V' _chemical_formula_sum 'C17 H19 N2 O4 V' _chemical_formula_weight 366.28 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' V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-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 13.3526(8) _cell_length_b 9.5984(6) _cell_length_c 26.3471(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3376.7(3) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 0.610 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7500 _exptl_absorpt_correction_T_max 0.9528 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25699 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0298 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4190 _reflns_number_gt 2681 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0533P)^2^+3.4560P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4190 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0875 _refine_ls_R_factor_gt 0.0555 _refine_ls_wR_factor_ref 0.1565 _refine_ls_wR_factor_gt 0.1338 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.96736(4) 0.13720(5) 0.75072(2) 0.04929(18) Uani 1 1 d . . . O1 O 0.96502(17) 0.1020(3) 0.82295(9) 0.0678(6) Uani 1 1 d . . . O2 O 1.1320(2) 0.0717(4) 0.87317(13) 0.0831(9) Uani 1 1 d . . . O3 O 1.08829(17) 0.1445(2) 0.74485(8) 0.0621(6) Uani 1 1 d . . . O4 O 0.9206(2) 0.2919(2) 0.74642(10) 0.0771(7) Uani 1 1 d . . . N1 N 0.85372(19) -0.0197(3) 0.74895(12) 0.0612(7) Uani 1 1 d . . . N2 N 0.95078(18) 0.0956(3) 0.67045(10) 0.0544(6) Uani 1 1 d . . . C1 C 0.8072(2) -0.0713(4) 0.78689(18) 0.0701(11) Uani 1 1 d . . . C2 C 0.8260(2) -0.0469(4) 0.83962(16) 0.0648(9) Uani 1 1 d . . . C3 C 0.9048(2) 0.0401(3) 0.85635(13) 0.0574(8) Uani 1 1 d . . . C4 C 0.9225(2) 0.0581(4) 0.90824(13) 0.0644(9) Uani 1 1 d . . . C5 C 0.8620(3) -0.0147(6) 0.9426(2) 0.0898(15) Uani 1 1 d . . . C6 C 0.7859(3) -0.0993(7) 0.9263(3) 0.115(2) Uani 1 1 d . . . C7 C 0.7675(3) -0.1158(5) 0.8762(3) 0.0931(16) Uani 1 1 d . . . C8 C 0.8214(4) -0.0648(5) 0.69825(18) 0.0830(13) Uani 1 1 d . . . C9 C 0.8461(3) 0.0501(4) 0.66187(17) 0.0720(10) Uani 1 1 d . . . C10 C 1.0221(3) -0.0110(5) 0.65376(18) 0.0781(11) Uani 1 1 d . . . C11 C 0.9675(4) 0.2238(5) 0.63993(18) 0.0802(12) Uani 1 1 d . . . C12 C 1.0013(3) 0.1531(4) 0.92891(12) 0.0643(9) Uani 1 1 d . . . C13 C 1.0996(3) 0.1560(4) 0.91096(13) 0.0665(9) Uani 1 1 d . . . C14 C 1.1704(4) 0.2427(5) 0.93322(16) 0.0862(13) Uani 1 1 d . . . C15 C 1.1452(7) 0.3277(5) 0.97259(19) 0.1070(19) Uani 1 1 d . . . C16 C 1.0504(7) 0.3275(6) 0.99084(19) 0.111(2) Uani 1 1 d . . . C17 C 0.9797(5) 0.2434(6) 0.96975(15) 0.0919(15) Uani 1 1 d . . . H2O H 1.095(3) 0.070(4) 0.8570(13) 0.049(12) Uiso 1 1 d . . . H1 H 0.756(3) -0.126(4) 0.7808(14) 0.077(11) Uiso 1 1 d . . . H5 H 0.873(3) -0.003(5) 0.9761(17) 0.094(15) Uiso 1 1 d . . . H6 H 0.754(4) -0.149(5) 0.9456(18) 0.105(15) Uiso 1 1 d . . . H7 H 0.722(3) -0.165(5) 0.8625(17) 0.100(17) Uiso 1 1 d . . . H8A H 0.753(4) -0.085(4) 0.6980(15) 0.090(12) Uiso 1 1 d . . . H8B H 0.869(4) -0.137(6) 0.687(2) 0.15(2) Uiso 1 1 d . . . H9A H 0.801(3) 0.143(5) 0.6726(18) 0.123(17) Uiso 1 1 d . . . H9B H 0.839(3) 0.016(4) 0.6225(14) 0.072(10) Uiso 1 1 d . . . H10A H 1.091(3) 0.043(3) 0.6552(12) 0.059(9) Uiso 1 1 d . . . H10B H 1.007(3) -0.040(4) 0.6180(16) 0.086(12) Uiso 1 1 d . . . H10C H 1.011(3) -0.096(5) 0.6777(17) 0.084(12) Uiso 1 1 d . . . H11A H 0.925(4) 0.294(6) 0.650(2) 0.12(2) Uiso 1 1 d . . . H11B H 0.954(3) 0.207(6) 0.602(2) 0.126(18) Uiso 1 1 d . . . H11C H 1.049(4) 0.247(6) 0.640(2) 0.14(2) Uiso 1 1 d . . . H14 H 1.227(3) 0.249(5) 0.9226(16) 0.083(16) Uiso 1 1 d . . . H15 H 1.191(3) 0.385(5) 0.9844(18) 0.100(16) Uiso 1 1 d . . . H16 H 1.037(4) 0.390(6) 1.015(2) 0.124(18) Uiso 1 1 d . . . H17 H 0.911(3) 0.233(4) 0.9791(14) 0.072(12) 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 0.0435(3) 0.0389(3) 0.0655(3) -0.0090(2) 0.0084(2) -0.00771(19) O1 0.0674(14) 0.0738(15) 0.0621(14) -0.0044(11) 0.0162(11) -0.0283(12) O2 0.0538(16) 0.112(2) 0.084(2) -0.0417(18) 0.0111(15) -0.0082(16) O3 0.0498(12) 0.0694(14) 0.0670(14) -0.0108(11) 0.0066(10) -0.0120(11) O4 0.0893(19) 0.0484(13) 0.0936(18) -0.0177(12) 0.0020(14) 0.0108(13) N1 0.0430(13) 0.0465(13) 0.094(2) 0.0010(14) -0.0070(14) -0.0094(11) N2 0.0462(13) 0.0465(13) 0.0704(17) -0.0083(12) -0.0034(12) 0.0003(11) C1 0.0373(16) 0.0505(19) 0.122(4) 0.016(2) -0.0014(18) -0.0110(14) C2 0.0360(15) 0.0586(19) 0.100(3) 0.0219(18) 0.0123(16) 0.0026(14) C3 0.0448(16) 0.0509(17) 0.077(2) 0.0120(15) 0.0182(15) 0.0061(13) C4 0.0537(18) 0.068(2) 0.072(2) 0.0210(17) 0.0241(16) 0.0252(16) C5 0.061(2) 0.119(4) 0.090(3) 0.043(3) 0.027(2) 0.024(2) C6 0.057(3) 0.151(5) 0.136(5) 0.086(4) 0.028(3) 0.007(3) C7 0.043(2) 0.098(3) 0.138(5) 0.055(3) 0.012(2) 0.001(2) C8 0.073(3) 0.075(3) 0.101(3) 0.002(2) -0.025(2) -0.031(2) C9 0.059(2) 0.065(2) 0.092(3) -0.007(2) -0.0157(19) -0.0089(18) C10 0.080(3) 0.081(3) 0.074(3) -0.018(2) -0.007(2) 0.021(2) C11 0.101(4) 0.063(2) 0.076(3) 0.009(2) -0.006(2) -0.009(2) C12 0.084(2) 0.0581(18) 0.0504(17) 0.0084(14) 0.0134(16) 0.0252(18) C13 0.078(2) 0.062(2) 0.060(2) -0.0059(16) 0.0087(17) 0.0009(18) C14 0.112(4) 0.085(3) 0.062(2) -0.009(2) -0.005(3) -0.016(3) C15 0.180(7) 0.076(3) 0.065(3) -0.007(2) -0.028(4) -0.005(4) C16 0.194(7) 0.082(3) 0.057(3) -0.016(2) -0.013(4) 0.046(4) C17 0.123(4) 0.099(3) 0.054(2) 0.010(2) 0.018(3) 0.053(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 O4 1.615(2) . ? V1 O3 1.624(2) . ? V1 O1 1.933(2) . ? V1 N1 2.138(2) . ? V1 N2 2.164(3) . ? O1 C3 1.332(4) . ? O2 C13 1.353(4) . ? O2 H2O 0.65(3) . ? N1 C1 1.277(5) . ? N1 C8 1.469(5) . ? N2 C10 1.466(5) . ? N2 C9 1.482(4) . ? N2 C11 1.486(5) . ? C1 C2 1.431(6) . ? C1 H1 0.87(4) . ? C2 C7 1.406(5) . ? C2 C3 1.414(5) . ? C3 C4 1.398(5) . ? C4 C5 1.400(5) . ? C4 C12 1.495(5) . ? C5 C6 1.370(8) . ? C5 H5 0.90(4) . ? C6 C7 1.351(8) . ? C6 H6 0.82(5) . ? C7 H7 0.85(5) . ? C8 C9 1.498(6) . ? C8 H8A 0.93(5) . ? C8 H8B 0.99(6) . ? C9 H9A 1.12(5) . ? C9 H9B 1.09(4) . ? C10 H10A 1.05(3) . ? C10 H10B 1.01(4) . ? C10 H10C 1.04(4) . ? C11 H11A 0.92(5) . ? C11 H11B 1.03(6) . ? C11 H11C 1.11(5) . ? C12 C13 1.395(5) . ? C12 C17 1.411(6) . ? C13 C14 1.389(6) . ? C14 C15 1.362(7) . ? C14 H14 0.81(4) . ? C15 C16 1.354(8) . ? C15 H15 0.88(5) . ? C16 C17 1.361(8) . ? C16 H16 0.89(6) . ? C17 H17 0.95(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 O4 V1 O3 109.75(14) . . ? O4 V1 O1 102.93(12) . . ? O3 V1 O1 96.75(10) . . ? O4 V1 N1 111.82(13) . . ? O3 V1 N1 137.24(11) . . ? O1 V1 N1 83.51(11) . . ? O4 V1 N2 93.52(12) . . ? O3 V1 N2 90.95(10) . . ? O1 V1 N2 158.19(11) . . ? N1 V1 N2 77.07(11) . . ? C3 O1 V1 137.6(2) . . ? C13 O2 H2O 104(3) . . ? C1 N1 C8 117.0(3) . . ? C1 N1 V1 127.0(3) . . ? C8 N1 V1 115.8(2) . . ? C10 N2 C9 111.2(3) . . ? C10 N2 C11 108.6(4) . . ? C9 N2 C11 107.6(3) . . ? C10 N2 V1 110.8(2) . . ? C9 N2 V1 107.5(2) . . ? C11 N2 V1 111.2(2) . . ? N1 C1 C2 127.7(3) . . ? N1 C1 H1 118(3) . . ? C2 C1 H1 114(3) . . ? C7 C2 C3 118.5(4) . . ? C7 C2 C1 119.5(4) . . ? C3 C2 C1 122.0(3) . . ? O1 C3 C4 119.3(3) . . ? O1 C3 C2 120.5(3) . . ? C4 C3 C2 120.3(3) . . ? C3 C4 C5 118.2(4) . . ? C3 C4 C12 123.4(3) . . ? C5 C4 C12 118.4(4) . . ? C6 C5 C4 121.5(5) . . ? C6 C5 H5 120(3) . . ? C4 C5 H5 119(3) . . ? C7 C6 C5 120.6(4) . . ? C7 C6 H6 116(4) . . ? C5 C6 H6 123(4) . . ? C6 C7 C2 121.0(5) . . ? C6 C7 H7 127(3) . . ? C2 C7 H7 112(3) . . ? N1 C8 C9 107.5(3) . . ? N1 C8 H8A 111(3) . . ? C9 C8 H8A 111(3) . . ? N1 C8 H8B 106(3) . . ? C9 C8 H8B 101(3) . . ? H8A C8 H8B 119(4) . . ? N2 C9 C8 109.1(3) . . ? N2 C9 H9A 104(2) . . ? C8 C9 H9A 108(2) . . ? N2 C9 H9B 108.3(19) . . ? C8 C9 H9B 111.8(19) . . ? H9A C9 H9B 116(3) . . ? N2 C10 H10A 102.2(18) . . ? N2 C10 H10B 110(2) . . ? H10A C10 H10B 110(3) . . ? N2 C10 H10C 106(2) . . ? H10A C10 H10C 119(3) . . ? H10B C10 H10C 109(3) . . ? N2 C11 H11A 110(3) . . ? N2 C11 H11B 112(3) . . ? H11A C11 H11B 107(4) . . ? N2 C11 H11C 108(3) . . ? H11A C11 H11C 117(4) . . ? H11B C11 H11C 102(4) . . ? C13 C12 C17 116.0(4) . . ? C13 C12 C4 123.4(3) . . ? C17 C12 C4 120.5(4) . . ? O2 C13 C14 116.8(4) . . ? O2 C13 C12 122.6(3) . . ? C14 C13 C12 120.6(4) . . ? C15 C14 C13 120.8(6) . . ? C15 C14 H14 117(3) . . ? C13 C14 H14 122(3) . . ? C16 C15 C14 120.0(6) . . ? C16 C15 H15 122(3) . . ? C14 C15 H15 118(3) . . ? C15 C16 C17 120.3(5) . . ? C15 C16 H16 116(3) . . ? C17 C16 H16 124(3) . . ? C16 C17 C12 122.2(5) . . ? C16 C17 H17 128(2) . . ? C12 C17 H17 109(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 O4 V1 O1 C3 95.1(3) . . . . ? O3 V1 O1 C3 -152.8(3) . . . . ? N1 V1 O1 C3 -15.9(3) . . . . ? N2 V1 O1 C3 -42.9(5) . . . . ? O4 V1 N1 C1 -90.0(3) . . . . ? O3 V1 N1 C1 104.3(3) . . . . ? O1 V1 N1 C1 11.3(3) . . . . ? N2 V1 N1 C1 -178.6(3) . . . . ? O4 V1 N1 C8 85.3(3) . . . . ? O3 V1 N1 C8 -80.4(3) . . . . ? O1 V1 N1 C8 -173.3(3) . . . . ? N2 V1 N1 C8 -3.3(3) . . . . ? O4 V1 N2 C10 155.8(3) . . . . ? O3 V1 N2 C10 45.9(3) . . . . ? O1 V1 N2 C10 -65.0(4) . . . . ? N1 V1 N2 C10 -92.7(3) . . . . ? O4 V1 N2 C9 -82.6(2) . . . . ? O3 V1 N2 C9 167.5(2) . . . . ? O1 V1 N2 C9 56.6(4) . . . . ? N1 V1 N2 C9 29.0(2) . . . . ? O4 V1 N2 C11 34.9(3) . . . . ? O3 V1 N2 C11 -74.9(3) . . . . ? O1 V1 N2 C11 174.1(3) . . . . ? N1 V1 N2 C11 146.5(3) . . . . ? C8 N1 C1 C2 178.3(4) . . . . ? V1 N1 C1 C2 -6.4(5) . . . . ? N1 C1 C2 C7 -178.8(4) . . . . ? N1 C1 C2 C3 -1.6(6) . . . . ? V1 O1 C3 C4 -168.9(2) . . . . ? V1 O1 C3 C2 13.4(5) . . . . ? C7 C2 C3 O1 176.8(3) . . . . ? C1 C2 C3 O1 -0.4(5) . . . . ? C7 C2 C3 C4 -1.0(5) . . . . ? C1 C2 C3 C4 -178.2(3) . . . . ? O1 C3 C4 C5 -176.2(3) . . . . ? C2 C3 C4 C5 1.5(5) . . . . ? O1 C3 C4 C12 5.1(5) . . . . ? C2 C3 C4 C12 -177.2(3) . . . . ? C3 C4 C5 C6 -1.3(6) . . . . ? C12 C4 C5 C6 177.5(4) . . . . ? C4 C5 C6 C7 0.5(8) . . . . ? C5 C6 C7 C2 0.1(8) . . . . ? C3 C2 C7 C6 0.1(6) . . . . ? C1 C2 C7 C6 177.4(4) . . . . ? C1 N1 C8 C9 153.0(4) . . . . ? V1 N1 C8 C9 -22.8(5) . . . . ? C10 N2 C9 C8 70.3(5) . . . . ? C11 N2 C9 C8 -171.0(4) . . . . ? V1 N2 C9 C8 -51.1(4) . . . . ? N1 C8 C9 N2 48.2(5) . . . . ? C3 C4 C12 C13 -47.3(5) . . . . ? C5 C4 C12 C13 134.0(4) . . . . ? C3 C4 C12 C17 134.9(3) . . . . ? C5 C4 C12 C17 -43.9(5) . . . . ? C17 C12 C13 O2 177.7(4) . . . . ? C4 C12 C13 O2 -0.3(6) . . . . ? C17 C12 C13 C14 0.7(5) . . . . ? C4 C12 C13 C14 -177.3(4) . . . . ? O2 C13 C14 C15 -177.9(4) . . . . ? C12 C13 C14 C15 -0.7(7) . . . . ? C13 C14 C15 C16 0.6(8) . . . . ? C14 C15 C16 C17 -0.5(8) . . . . ? C15 C16 C17 C12 0.5(7) . . . . ? C13 C12 C17 C16 -0.6(6) . . . . ? C4 C12 C17 C16 177.5(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.497 _refine_diff_density_min -0.397 _refine_diff_density_rms 0.057 #===END data_plitt15a _database_code_depnum_ccdc_archive 'CCDC 233276' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H15 N2 O3 V' _chemical_formula_sum 'C19 H15 N2 O3 V' _chemical_formula_weight 370.27 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' V V 0.3005 0.5294 '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 6.7529(10) _cell_length_b 9.6314(13) _cell_length_c 24.337(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1582.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.648 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8394 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details SADABS _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 graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15110 _diffrn_reflns_av_R_equivalents 0.0762 _diffrn_reflns_av_sigmaI/netI 0.0961 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 32.11 _reflns_number_total 5408 _reflns_number_gt 3940 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0898P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _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 0.37(4) _refine_ls_number_reflns 5408 _refine_ls_number_parameters 287 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1028 _refine_ls_R_factor_gt 0.0625 _refine_ls_wR_factor_ref 0.1676 _refine_ls_wR_factor_gt 0.1413 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 V1 V 0.22267(8) 0.28412(5) 0.19369(2) 0.01438(13) Uani 1 1 d . . . O1 O 0.2616(4) 0.4085(2) 0.13403(9) 0.0187(5) Uani 1 1 d . . . O2 O -0.0029(4) 0.2300(3) 0.18486(10) 0.0266(6) Uani 1 1 d . . . O3 O 0.3766(6) 0.1619(3) 0.17658(12) 0.0347(8) Uani 1 1 d . . . N1 N 0.2557(4) 0.4654(3) 0.24296(10) 0.0143(5) Uani 1 1 d . . . N2 N 0.2322(4) 0.2111(3) 0.27616(11) 0.0155(5) Uani 1 1 d . . . C1 C 0.2701(5) 0.5934(3) 0.22627(13) 0.0148(6) Uani 1 1 d . . . C2 C 0.2726(6) 0.6387(3) 0.16986(13) 0.0151(6) Uani 1 1 d . . . C3 C 0.2666(5) 0.5436(3) 0.12585(13) 0.0146(6) Uani 1 1 d . . . C4 C 0.2707(6) 0.5955(3) 0.07129(13) 0.0155(6) Uani 1 1 d . . . C5 C 0.2884(6) 0.7389(4) 0.06311(14) 0.0182(6) Uani 1 1 d . . . C6 C 0.2944(6) 0.8340(4) 0.10673(15) 0.0186(7) Uani 1 1 d . . . C7 C 0.2860(5) 0.7825(4) 0.15951(13) 0.0163(6) Uani 1 1 d . . . C8 C 0.2561(6) 0.5005(3) 0.02332(13) 0.0164(6) Uani 1 1 d . . . C9 C 0.0910(6) 0.4145(4) 0.01622(16) 0.0207(7) Uani 1 1 d . . . C10 C 0.0688(7) 0.3358(4) -0.03115(17) 0.0248(8) Uani 1 1 d . . . C11 C 0.2160(7) 0.3366(4) -0.07124(15) 0.0241(8) Uani 1 1 d . . . C12 C 0.3830(7) 0.4159(5) -0.06360(16) 0.0254(8) Uani 1 1 d . . . C13 C 0.4031(6) 0.4991(4) -0.01701(15) 0.0209(7) Uani 1 1 d . . . C14 C 0.2481(5) 0.4505(3) 0.30326(14) 0.0176(6) Uani 1 1 d . . . C15 C 0.2391(5) 0.2994(3) 0.31807(13) 0.0155(6) Uani 1 1 d . . . C16 C 0.2265(6) 0.0724(3) 0.28703(14) 0.0179(6) Uani 1 1 d . . . C17 C 0.2302(6) 0.0204(4) 0.33947(14) 0.0194(6) Uani 1 1 d . . . C18 C 0.2374(6) 0.1147(4) 0.38345(15) 0.0206(7) Uani 1 1 d . . . C19 C 0.2406(5) 0.2552(4) 0.37276(14) 0.0181(6) Uani 1 1 d . . . H1 H 0.268(7) 0.670(4) 0.2559(15) 0.021(10) Uiso 1 1 d . . . H5 H 0.284(6) 0.766(4) 0.0268(15) 0.013(9) Uiso 1 1 d . . . H6 H 0.305(7) 0.940(4) 0.0985(16) 0.016(10) Uiso 1 1 d . . . H7 H 0.293(6) 0.846(4) 0.1909(15) 0.013(9) Uiso 1 1 d . . . H9 H -0.013(7) 0.405(4) 0.0497(16) 0.014(10) Uiso 1 1 d . . . H10 H -0.029(10) 0.268(7) -0.037(2) 0.064(19) Uiso 1 1 d . . . H11 H 0.204(7) 0.285(5) -0.1030(17) 0.024(11) Uiso 1 1 d . . . H12 H 0.498(7) 0.413(5) -0.0939(16) 0.016(11) Uiso 1 1 d . . . H13 H 0.498(7) 0.557(4) -0.0130(16) 0.016(11) Uiso 1 1 d . . . H14A H 0.351(8) 0.496(5) 0.3202(18) 0.026(12) Uiso 1 1 d . . . H14B H 0.129(7) 0.494(5) 0.3248(18) 0.022(12) Uiso 1 1 d . . . H16 H 0.223(6) 0.013(4) 0.2542(14) 0.009(9) Uiso 1 1 d . . . H17 H 0.235(8) -0.084(5) 0.3419(16) 0.026(11) Uiso 1 1 d . . . H18 H 0.264(8) 0.082(5) 0.4235(17) 0.028(12) Uiso 1 1 d . . . H19 H 0.240(8) 0.322(4) 0.3990(16) 0.018(10) 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 0.0106(2) 0.0133(2) 0.0193(2) -0.0005(2) 0.0002(2) 0.0011(2) O1 0.0197(14) 0.0143(10) 0.0219(11) -0.0001(8) 0.0005(10) -0.0021(11) O2 0.0248(14) 0.0313(15) 0.0235(13) 0.0051(12) -0.0053(10) -0.0146(12) O3 0.045(2) 0.0295(15) 0.0292(15) 0.0064(12) 0.0131(13) 0.0177(15) N1 0.0094(14) 0.0153(11) 0.0183(12) 0.0002(9) 0.0012(10) -0.0002(11) N2 0.0064(11) 0.0175(12) 0.0225(12) 0.0005(10) -0.0011(10) -0.0014(13) C1 0.0070(13) 0.0158(13) 0.0215(14) -0.0023(11) 0.0015(12) -0.0009(13) C2 0.0038(13) 0.0169(13) 0.0248(15) 0.0010(11) 0.0025(12) 0.0003(13) C3 0.0063(14) 0.0147(13) 0.0229(14) 0.0009(11) -0.0012(12) -0.0022(12) C4 0.0086(14) 0.0170(13) 0.0210(14) 0.0000(11) -0.0016(12) -0.0005(13) C5 0.0127(14) 0.0192(15) 0.0228(15) 0.0042(12) -0.0018(12) 0.0007(13) C6 0.0102(16) 0.0175(15) 0.0282(17) 0.0020(13) 0.0006(13) 0.0019(13) C7 0.0085(13) 0.0149(13) 0.0254(14) -0.0021(13) 0.0000(12) -0.0006(15) C8 0.0150(17) 0.0150(13) 0.0191(13) 0.0019(11) 0.0003(12) 0.0026(13) C9 0.0152(17) 0.0193(17) 0.0275(18) -0.0014(14) 0.0033(14) -0.0012(14) C10 0.021(2) 0.0214(18) 0.032(2) -0.0020(16) -0.0044(16) -0.0019(15) C11 0.032(2) 0.0185(15) 0.0223(17) -0.0002(13) -0.0018(17) 0.0029(17) C12 0.027(2) 0.029(2) 0.0201(17) 0.0024(15) 0.0052(14) 0.0037(17) C13 0.0156(17) 0.0228(18) 0.0243(18) 0.0028(15) 0.0013(13) -0.0020(14) C14 0.0161(18) 0.0184(13) 0.0183(14) -0.0016(12) -0.0012(14) -0.0010(13) C15 0.0053(14) 0.0192(14) 0.0222(14) -0.0007(11) 0.0000(10) 0.0022(12) C16 0.0097(15) 0.0172(14) 0.0266(15) 0.0002(12) -0.0032(13) 0.0005(14) C17 0.0099(15) 0.0197(15) 0.0287(16) 0.0031(12) -0.0014(14) -0.0003(14) C18 0.0131(17) 0.0225(16) 0.0263(16) 0.0059(13) 0.0006(14) -0.0042(14) C19 0.0085(15) 0.0229(15) 0.0230(14) 0.0017(12) 0.0010(12) 0.0000(12) _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 O2 1.624(3) . ? V1 O3 1.625(3) . ? V1 O1 1.900(2) . ? V1 N2 2.128(3) . ? V1 N1 2.130(3) . ? O1 C3 1.317(4) . ? N1 C1 1.302(4) . ? N1 C14 1.476(4) . ? N2 C15 1.329(4) . ? N2 C16 1.362(4) . ? C1 C2 1.440(4) . ? C1 H1 1.03(4) . ? C2 C3 1.410(4) . ? C2 C7 1.411(4) . ? C3 C4 1.419(4) . ? C4 C5 1.400(5) . ? C4 C8 1.487(4) . ? C5 C6 1.403(5) . ? C5 H5 0.92(4) . ? C6 C7 1.378(5) . ? C6 H6 1.04(4) . ? C7 H7 0.98(4) . ? C8 C13 1.396(5) . ? C8 C9 1.400(5) . ? C9 C10 1.388(6) . ? C9 H9 1.08(4) . ? C10 C11 1.393(6) . ? C10 H10 0.94(7) . ? C11 C12 1.374(6) . ? C11 H11 0.92(4) . ? C12 C13 1.395(6) . ? C12 H12 1.07(4) . ? C13 H13 0.86(5) . ? C14 C15 1.500(4) . ? C14 H14A 0.92(5) . ? C14 H14B 1.05(5) . ? C15 C19 1.397(4) . ? C16 C17 1.371(5) . ? C16 H16 0.98(3) . ? C17 C18 1.405(5) . ? C17 H17 1.01(4) . ? C18 C19 1.378(5) . ? C18 H18 1.04(4) . ? C19 H19 0.91(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 O2 V1 O3 109.5(2) . . ? O2 V1 O1 103.35(13) . . ? O3 V1 O1 99.92(13) . . ? O2 V1 N2 92.71(12) . . ? O3 V1 N2 89.02(13) . . ? O1 V1 N2 157.64(11) . . ? O2 V1 N1 115.84(14) . . ? O3 V1 N1 132.18(16) . . ? O1 V1 N1 84.20(10) . . ? N2 V1 N1 74.74(10) . . ? C3 O1 V1 137.9(2) . . ? C1 N1 C14 113.9(3) . . ? C1 N1 V1 127.5(2) . . ? C14 N1 V1 118.44(19) . . ? C15 N2 C16 118.6(3) . . ? C15 N2 V1 120.9(2) . . ? C16 N2 V1 120.4(2) . . ? N1 C1 C2 125.8(3) . . ? N1 C1 H1 117(2) . . ? C2 C1 H1 117(2) . . ? C3 C2 C7 120.3(3) . . ? C3 C2 C1 121.8(3) . . ? C7 C2 C1 117.9(3) . . ? O1 C3 C2 121.8(3) . . ? O1 C3 C4 119.4(3) . . ? C2 C3 C4 118.8(3) . . ? C5 C4 C3 118.8(3) . . ? C5 C4 C8 120.1(3) . . ? C3 C4 C8 121.1(3) . . ? C4 C5 C6 122.6(3) . . ? C4 C5 H5 115(2) . . ? C6 C5 H5 122(2) . . ? C7 C6 C5 118.0(3) . . ? C7 C6 H6 122(2) . . ? C5 C6 H6 120(2) . . ? C6 C7 C2 121.5(3) . . ? C6 C7 H7 120(2) . . ? C2 C7 H7 119(2) . . ? C13 C8 C9 118.3(3) . . ? C13 C8 C4 120.7(3) . . ? C9 C8 C4 120.9(3) . . ? C10 C9 C8 120.8(4) . . ? C10 C9 H9 121(2) . . ? C8 C9 H9 118(2) . . ? C9 C10 C11 120.1(4) . . ? C9 C10 H10 125(4) . . ? C11 C10 H10 114(4) . . ? C12 C11 C10 119.6(4) . . ? C12 C11 H11 119(3) . . ? C10 C11 H11 121(3) . . ? C11 C12 C13 120.6(4) . . ? C11 C12 H12 119(2) . . ? C13 C12 H12 120(2) . . ? C12 C13 C8 120.5(4) . . ? C12 C13 H13 123(3) . . ? C8 C13 H13 116(3) . . ? N1 C14 C15 109.6(3) . . ? N1 C14 H14A 112(3) . . ? C15 C14 H14A 113(3) . . ? N1 C14 H14B 119(2) . . ? C15 C14 H14B 104(2) . . ? H14A C14 H14B 99(3) . . ? N2 C15 C19 122.5(3) . . ? N2 C15 C14 115.9(3) . . ? C19 C15 C14 121.6(3) . . ? N2 C16 C17 122.6(3) . . ? N2 C16 H16 114(2) . . ? C17 C16 H16 123(2) . . ? C16 C17 C18 118.2(3) . . ? C16 C17 H17 115(2) . . ? C18 C17 H17 127(2) . . ? C19 C18 C17 119.5(3) . . ? C19 C18 H18 118(2) . . ? C17 C18 H18 122(2) . . ? C18 C19 C15 118.6(3) . . ? C18 C19 H19 124(2) . . ? C15 C19 H19 117(2) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 32.11 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.883 _refine_diff_density_min -1.027 _refine_diff_density_rms 0.133 #===END data_plitt12 _database_code_depnum_ccdc_archive 'CCDC 233277' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H20 N O5 V, C3 H8 O' _chemical_formula_sum 'C25 H28 N O6 V' _chemical_formula_weight 489.42 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 Cc 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 12.4475(6) _cell_length_b 29.3169(14) _cell_length_c 6.9933(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.7640(10) _cell_angle_gamma 90.00 _cell_volume 2335.63(19) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.466 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8357 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(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 'CCD area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14146 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0494 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 43 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 32.00 _reflns_number_total 7507 _reflns_number_gt 6875 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0453P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom and difmap' _refine_ls_hydrogen_treatment mixed _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 -0.004(12) _refine_ls_number_reflns 7507 _refine_ls_number_parameters 404 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0408 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0845 _refine_ls_wR_factor_gt 0.0804 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.029 _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 V1 V 0.59373(2) 0.899070(8) 0.36320(3) 0.01115(6) Uani 1 1 d . . . O1 O 0.74423(10) 0.88907(4) 0.55930(18) 0.0136(2) Uani 1 1 d . . . O2 O 0.43602(10) 0.88844(4) 0.32831(19) 0.0154(2) Uani 1 1 d . . . O3 O 1.11480(11) 0.84716(5) 0.9275(2) 0.0193(3) Uani 1 1 d . . . O4 O 0.59871(11) 0.94307(4) 0.23269(19) 0.0170(2) Uani 1 1 d . . . O5 O 0.58642(10) 0.85223(4) 0.20162(18) 0.0149(2) Uani 1 1 d . . . O6 O 0.81762(11) 0.69356(5) 0.6496(2) 0.0242(3) Uani 1 1 d . . . N1 N 0.57973(11) 0.93672(4) 0.6198(2) 0.0115(2) Uani 1 1 d . . . C1 C 0.66603(13) 0.95417(5) 0.7790(2) 0.0121(3) Uani 1 1 d . . . C2 C 0.78726(13) 0.94864(5) 0.8142(2) 0.0119(3) Uani 1 1 d . . . C3 C 0.82302(12) 0.91678(5) 0.6993(2) 0.0115(3) Uani 1 1 d . . . C4 C 0.94312(12) 0.91272(5) 0.7364(2) 0.0122(3) Uani 1 1 d . . . C5 C 1.02350(13) 0.94052(5) 0.8897(3) 0.0147(3) Uani 1 1 d . . . C6 C 0.98949(14) 0.97136(6) 1.0062(3) 0.0161(3) Uani 1 1 d . . . C7 C 0.87259(14) 0.97510(6) 0.9711(3) 0.0140(3) Uani 1 1 d . . . C8 C 0.98269(13) 0.88085(5) 0.6125(2) 0.0133(3) Uani 1 1 d . . . C9 C 1.07385(13) 0.84965(6) 0.7149(3) 0.0147(3) Uani 1 1 d . . . C10 C 1.11713(14) 0.82217(6) 0.5995(3) 0.0183(3) Uani 1 1 d . . . C11 C 1.07072(15) 0.82554(7) 0.3831(3) 0.0202(3) Uani 1 1 d . . . C12 C 0.98057(15) 0.85599(6) 0.2796(3) 0.0197(3) Uani 1 1 d . . . C13 C 0.93669(14) 0.88322(6) 0.3941(3) 0.0163(3) Uani 1 1 d . . . C15 C 0.46174(12) 0.94139(5) 0.5958(2) 0.0128(3) Uani 1 1 d . . . C16 C 0.38600(12) 0.91459(5) 0.4300(2) 0.0131(3) Uani 1 1 d . . . C17 C 0.26601(14) 0.91360(6) 0.3831(3) 0.0160(3) Uani 1 1 d . . . C18 C 0.22351(14) 0.93928(6) 0.5054(3) 0.0179(3) Uani 1 1 d . . . C19 C 0.29898(14) 0.96600(6) 0.6707(3) 0.0183(3) Uani 1 1 d . . . C20 C 0.41858(14) 0.96723(6) 0.7167(3) 0.0156(3) Uani 1 1 d . . . C21 C 0.57801(16) 0.85023(6) -0.0102(3) 0.0187(3) Uani 1 1 d . . . C22 C 0.45177(18) 0.84107(7) -0.1561(3) 0.0265(4) Uani 1 1 d . . . C23 C 0.6619(2) 0.81375(9) -0.0209(4) 0.0327(5) Uani 1 1 d . . . C26 C 0.7954(3) 0.77156(8) 0.5579(5) 0.0439(7) Uani 1 1 d . . . C24 C 0.8807(3) 0.73664(9) 0.6909(5) 0.0206(7) Uani 0.680(7) 1 d P A 1 H24 H 0.9491 0.7344 0.6506 0.038(5) Uiso 0.680(7) 1 calc PR A 1 C25 C 0.9227(4) 0.74960(12) 0.9181(5) 0.0353(9) Uani 0.680(7) 1 d P A 1 H25A H 0.8556 0.7511 0.9573 0.038(5) Uiso 0.680(7) 1 calc PR A 1 H25B H 0.9614 0.7794 0.9406 0.038(5) Uiso 0.680(7) 1 calc PR A 1 H25C H 0.9786 0.7267 1.0042 0.038(5) Uiso 0.680(7) 1 calc PR A 1 C25A C 0.9708(7) 0.7418(3) 0.8687(13) 0.0324(17) Uiso 0.320(7) 1 d P A 2 H25D H 1.0000 0.7172 0.9720 0.038(5) Uiso 0.320(7) 1 calc PR A 2 H25E H 0.9892 0.7713 0.9400 0.038(5) Uiso 0.320(7) 1 calc PR A 2 H25F H 1.0084 0.7397 0.7700 0.038(5) Uiso 0.320(7) 1 calc PR A 2 C24A C 0.8410(6) 0.7373(2) 0.7531(11) 0.0255(15) Uiso 0.320(7) 1 d P A 2 H24A H 0.7982 0.7414 0.8462 0.038(5) Uiso 0.320(7) 1 calc PR A 2 H3O H 1.171(2) 0.8327(10) 0.977(4) 0.032(7) Uiso 1 1 d . . . H6O H 0.861(2) 0.6719(8) 0.706(4) 0.023(6) Uiso 1 1 d . . . H1 H 0.6505(19) 0.9717(8) 0.875(4) 0.018(5) Uiso 1 1 d . . . H5 H 1.102(2) 0.9387(8) 0.907(4) 0.031(7) Uiso 1 1 d . . . H6 H 1.0455(17) 0.9880(7) 1.116(3) 0.012(5) Uiso 1 1 d . . . H7 H 0.855(2) 0.9943(8) 1.055(4) 0.020(5) Uiso 1 1 d . . . H10 H 1.175(2) 0.8011(8) 0.671(4) 0.026(6) Uiso 1 1 d . . . H11 H 1.108(2) 0.8081(8) 0.315(4) 0.030(7) Uiso 1 1 d . . . H12 H 0.953(2) 0.8593(9) 0.142(4) 0.032(7) Uiso 1 1 d . . . H13 H 0.8749(18) 0.9032(6) 0.323(3) 0.005(4) Uiso 1 1 d . . . H17 H 0.217(2) 0.8924(8) 0.269(4) 0.028(7) Uiso 1 1 d . . . H18 H 0.150(2) 0.9369(8) 0.486(4) 0.023(6) Uiso 1 1 d . . . H19 H 0.274(2) 0.9825(8) 0.752(4) 0.022(6) Uiso 1 1 d . . . H20 H 0.4690(19) 0.9871(8) 0.830(4) 0.018(5) Uiso 1 1 d . . . H21 H 0.6027(18) 0.8788(7) -0.044(3) 0.012(5) Uiso 1 1 d . . . H22A H 0.395(2) 0.8637(9) -0.139(4) 0.035(7) Uiso 1 1 d . . . H22C H 0.451(2) 0.8396(9) -0.277(5) 0.033(7) Uiso 1 1 d . . . H23A H 0.732(3) 0.8196(10) 0.070(5) 0.046(8) Uiso 1 1 d . . . H23B H 0.631(2) 0.7838(10) -0.007(4) 0.038(7) Uiso 1 1 d . . . H23C H 0.660(3) 0.8140(11) -0.150(5) 0.048(9) Uiso 1 1 d . . . H26A H 0.819(3) 0.7999(11) 0.582(5) 0.046(5) Uiso 1 1 d . . . H26B H 0.792(3) 0.7667(10) 0.409(5) 0.046(5) Uiso 1 1 d . . . H26C H 0.725(3) 0.7705(10) 0.534(5) 0.046(5) Uiso 1 1 d . . . H122 H 0.427(2) 0.8137(9) -0.115(4) 0.025(6) 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 0.01118(9) 0.01126(10) 0.01086(10) -0.00131(10) 0.00428(8) -0.00074(10) O1 0.0124(4) 0.0130(5) 0.0139(5) -0.0034(4) 0.0037(4) -0.0002(4) O2 0.0132(5) 0.0163(5) 0.0168(6) -0.0048(4) 0.0063(4) -0.0014(4) O3 0.0198(6) 0.0218(6) 0.0130(5) 0.0009(4) 0.0032(5) 0.0081(5) O4 0.0212(5) 0.0136(5) 0.0172(6) 0.0012(4) 0.0089(5) -0.0007(4) O5 0.0170(5) 0.0144(5) 0.0128(5) -0.0023(4) 0.0056(4) 0.0000(4) O6 0.0185(5) 0.0140(6) 0.0307(7) 0.0015(5) 0.0002(5) -0.0002(5) N1 0.0110(5) 0.0106(5) 0.0130(6) -0.0001(4) 0.0048(5) 0.0001(4) C1 0.0126(6) 0.0108(6) 0.0131(7) -0.0010(5) 0.0053(5) -0.0001(5) C2 0.0123(6) 0.0125(6) 0.0106(6) -0.0003(5) 0.0043(5) -0.0008(5) C3 0.0111(6) 0.0102(6) 0.0121(7) -0.0004(5) 0.0034(5) -0.0001(5) C4 0.0110(6) 0.0130(6) 0.0117(7) 0.0019(5) 0.0037(5) 0.0002(5) C5 0.0112(6) 0.0147(7) 0.0171(7) 0.0007(5) 0.0045(6) 0.0001(5) C6 0.0146(6) 0.0161(7) 0.0149(7) -0.0019(6) 0.0031(6) -0.0024(5) C7 0.0143(6) 0.0140(7) 0.0131(7) -0.0022(5) 0.0050(5) -0.0002(5) C8 0.0117(6) 0.0143(7) 0.0138(7) -0.0004(5) 0.0051(5) -0.0002(5) C9 0.0123(6) 0.0175(7) 0.0130(7) -0.0013(6) 0.0037(5) -0.0004(5) C10 0.0155(6) 0.0186(8) 0.0207(8) -0.0027(6) 0.0073(6) 0.0025(6) C11 0.0193(8) 0.0235(9) 0.0200(8) -0.0069(6) 0.0101(7) -0.0016(6) C12 0.0206(7) 0.0244(8) 0.0151(8) -0.0021(6) 0.0084(6) -0.0028(6) C13 0.0142(6) 0.0205(8) 0.0136(7) 0.0009(6) 0.0049(6) 0.0012(6) C15 0.0114(6) 0.0135(7) 0.0142(7) -0.0004(5) 0.0058(5) -0.0010(5) C16 0.0116(6) 0.0135(7) 0.0126(7) 0.0000(5) 0.0031(5) -0.0001(5) C17 0.0121(6) 0.0173(7) 0.0172(7) -0.0003(6) 0.0044(5) -0.0025(5) C18 0.0115(6) 0.0210(8) 0.0218(8) 0.0003(6) 0.0073(6) 0.0002(6) C19 0.0157(7) 0.0208(8) 0.0214(8) -0.0031(6) 0.0105(6) 0.0013(6) C20 0.0138(6) 0.0169(7) 0.0166(7) -0.0036(6) 0.0066(6) -0.0005(5) C21 0.0261(8) 0.0178(8) 0.0138(7) -0.0034(6) 0.0097(6) -0.0044(6) C22 0.0281(9) 0.0286(10) 0.0154(8) 0.0008(7) 0.0009(7) -0.0009(7) C23 0.0302(10) 0.0433(13) 0.0274(11) -0.0114(9) 0.0144(9) 0.0058(9) C26 0.0475(14) 0.0147(10) 0.0470(15) 0.0070(10) -0.0045(12) -0.0003(9) C24 0.0228(12) 0.0125(12) 0.0219(14) -0.0015(9) 0.0042(11) -0.0037(9) C25 0.045(2) 0.0288(17) 0.0248(15) -0.0076(12) 0.0067(14) -0.0058(14) _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 O4 1.5957(12) . ? V1 O5 1.7573(12) . ? V1 O1 1.8453(12) . ? V1 O2 1.9038(11) . ? V1 N1 2.1727(14) . ? O1 C3 1.3438(18) . ? O2 C16 1.3556(19) . ? O3 C9 1.365(2) . ? O3 H3O 0.77(3) . ? O5 C21 1.443(2) . ? O6 C24A 1.444(7) . ? O6 C24 1.453(3) . ? O6 H6O 0.82(3) . ? N1 C1 1.3006(19) . ? N1 C15 1.4161(19) . ? C1 C2 1.437(2) . ? C1 H1 0.93(2) . ? C2 C7 1.413(2) . ? C2 C3 1.416(2) . ? C3 C4 1.415(2) . ? C4 C5 1.397(2) . ? C4 C8 1.487(2) . ? C5 C6 1.392(2) . ? C5 H5 0.94(3) . ? C6 C7 1.379(2) . ? C6 H6 0.94(2) . ? C7 H7 0.90(2) . ? C8 C13 1.400(2) . ? C8 C9 1.408(2) . ? C9 C10 1.393(2) . ? C10 C11 1.388(3) . ? C10 H10 0.93(3) . ? C11 C12 1.388(3) . ? C11 H11 0.94(3) . ? C12 C13 1.389(2) . ? C12 H12 0.89(3) . ? C13 H13 0.94(2) . ? C15 C20 1.394(2) . ? C15 C16 1.403(2) . ? C16 C17 1.394(2) . ? C17 C18 1.394(3) . ? C17 H17 1.00(3) . ? C18 C19 1.399(2) . ? C18 H18 0.87(3) . ? C19 C20 1.391(2) . ? C19 H19 0.89(2) . ? C20 H20 0.98(2) . ? C21 C22 1.513(3) . ? C21 C23 1.517(3) . ? C21 H21 0.96(2) . ? C22 H22A 1.01(3) . ? C22 H22C 0.84(3) . ? C22 H122 0.94(3) . ? C23 H23A 0.87(3) . ? C23 H23B 0.98(3) . ? C23 H23C 0.89(4) . ? C26 C24 1.499(3) . ? C26 C24A 1.603(8) . ? C26 H26A 0.87(3) . ? C26 H26B 1.03(3) . ? C26 H26C 0.83(3) . ? C24 C25 1.508(4) . ? C24 H24 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C25A C24A 1.493(10) . ? C25A H25D 0.9800 . ? C25A H25E 0.9800 . ? C25A H25F 0.9800 . ? C24A H24A 1.0000 . ? 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 O4 V1 O5 105.53(6) . . ? O4 V1 O1 106.96(6) . . ? O5 V1 O1 97.34(5) . . ? O4 V1 O2 109.55(6) . . ? O5 V1 O2 90.35(5) . . ? O1 V1 O2 139.01(6) . . ? O4 V1 N1 95.53(6) . . ? O5 V1 N1 158.04(5) . . ? O1 V1 N1 82.08(5) . . ? O2 V1 N1 76.54(5) . . ? C3 O1 V1 132.04(10) . . ? C16 O2 V1 120.53(10) . . ? C9 O3 H3O 113(2) . . ? C21 O5 V1 130.93(10) . . ? C24A O6 H6O 118.9(17) . . ? C24 O6 H6O 112.2(17) . . ? C1 N1 C15 121.53(13) . . ? C1 N1 V1 126.39(10) . . ? C15 N1 V1 112.08(10) . . ? N1 C1 C2 123.39(14) . . ? N1 C1 H1 119.8(14) . . ? C2 C1 H1 116.8(14) . . ? C7 C2 C3 119.58(13) . . ? C7 C2 C1 118.67(14) . . ? C3 C2 C1 121.74(13) . . ? O1 C3 C4 119.33(14) . . ? O1 C3 C2 120.53(13) . . ? C4 C3 C2 120.10(13) . . ? C5 C4 C3 117.96(14) . . ? C5 C4 C8 120.74(13) . . ? C3 C4 C8 121.28(13) . . ? C6 C5 C4 122.38(14) . . ? C6 C5 H5 120.7(16) . . ? C4 C5 H5 116.9(16) . . ? C7 C6 C5 119.72(15) . . ? C7 C6 H6 119.1(13) . . ? C5 C6 H6 121.0(13) . . ? C6 C7 C2 120.22(15) . . ? C6 C7 H7 116.7(15) . . ? C2 C7 H7 123.1(15) . . ? C13 C8 C9 118.60(15) . . ? C13 C8 C4 121.25(14) . . ? C9 C8 C4 120.00(14) . . ? O3 C9 C10 122.54(15) . . ? O3 C9 C8 117.35(15) . . ? C10 C9 C8 120.09(15) . . ? C11 C10 C9 120.12(16) . . ? C11 C10 H10 121.6(16) . . ? C9 C10 H10 118.2(16) . . ? C12 C11 C10 120.55(16) . . ? C12 C11 H11 123.1(16) . . ? C10 C11 H11 116.2(16) . . ? C11 C12 C13 119.48(16) . . ? C11 C12 H12 120.8(17) . . ? C13 C12 H12 119.6(17) . . ? C12 C13 C8 121.15(15) . . ? C12 C13 H13 118.9(13) . . ? C8 C13 H13 119.9(13) . . ? C20 C15 C16 120.71(14) . . ? C20 C15 N1 127.99(14) . . ? C16 C15 N1 111.28(13) . . ? O2 C16 C17 122.65(14) . . ? O2 C16 C15 116.90(13) . . ? C17 C16 C15 120.35(15) . . ? C18 C17 C16 118.67(15) . . ? C18 C17 H17 123.9(16) . . ? C16 C17 H17 117.2(15) . . ? C17 C18 C19 121.00(14) . . ? C17 C18 H18 119.9(16) . . ? C19 C18 H18 118.9(16) . . ? C20 C19 C18 120.33(16) . . ? C20 C19 H19 117.1(16) . . ? C18 C19 H19 122.5(16) . . ? C19 C20 C15 118.94(15) . . ? C19 C20 H20 118.7(14) . . ? C15 C20 H20 122.3(14) . . ? O5 C21 C22 108.99(15) . . ? O5 C21 C23 108.20(16) . . ? C22 C21 C23 112.94(17) . . ? O5 C21 H21 108.9(12) . . ? C22 C21 H21 109.8(12) . . ? C23 C21 H21 108.0(12) . . ? C21 C22 H22A 113.0(15) . . ? C21 C22 H22C 105.9(18) . . ? H22A C22 H22C 115(2) . . ? C21 C22 H122 108.7(15) . . ? H22A C22 H122 101(2) . . ? H22C C22 H122 113(2) . . ? C21 C23 H23A 110(2) . . ? C21 C23 H23B 108.8(17) . . ? H23A C23 H23B 115(3) . . ? C21 C23 H23C 108(2) . . ? H23A C23 H23C 110(3) . . ? H23B C23 H23C 105(3) . . ? C24 C26 H26A 116(2) . . ? C24A C26 H26A 117(2) . . ? C24 C26 H26B 105.2(17) . . ? C24A C26 H26B 128.9(17) . . ? H26A C26 H26B 102(3) . . ? C24 C26 H26C 122(2) . . ? C24A C26 H26C 97(2) . . ? H26A C26 H26C 108(3) . . ? H26B C26 H26C 101(3) . . ? O6 C24 C26 106.2(2) . . ? O6 C24 C25 111.0(3) . . ? C26 C24 C25 109.9(3) . . ? O6 C24 H24 109.9 . . ? C26 C24 H24 109.9 . . ? C25 C24 H24 109.9 . . ? C24A C25A H25D 109.5 . . ? C24A C25A H25E 109.5 . . ? H25D C25A H25E 109.5 . . ? C24A C25A H25F 109.5 . . ? H25D C25A H25F 109.5 . . ? H25E C25A H25F 109.5 . . ? O6 C24A C25A 107.7(6) . . ? O6 C24A C26 101.5(4) . . ? C25A C24A C26 109.9(6) . . ? O6 C24A H24A 112.4 . . ? C25A C24A H24A 112.4 . . ? C26 C24A H24A 112.4 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 32.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.561 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.065 #===END data_plitt14 _database_code_depnum_ccdc_archive 'CCDC 233278' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H20 N O4 V' _chemical_formula_sum 'C22 H20 N O4 V' _chemical_formula_weight 413.33 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 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 8.0992(4) _cell_length_b 12.0724(5) _cell_length_c 19.3885(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1895.74(15) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.552 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8542 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(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 'CCD area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25656 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0393 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 32.04 _reflns_number_total 6309 _reflns_number_gt 5627 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0422P)^2^+0.4557P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _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 0.015(16) _refine_ls_number_reflns 6309 _refine_ls_number_parameters 333 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0857 _refine_ls_wR_factor_gt 0.0801 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 V1 V 0.23788(3) 0.533737(18) 0.408630(19) 0.01236(6) Uani 1 1 d . . . O1 O 0.21996(15) 0.63113(9) 0.48130(7) 0.0154(2) Uani 1 1 d . . . O2 O 0.38795(15) 0.47357(9) 0.34416(7) 0.0165(2) Uani 1 1 d . . . O3 O 0.23652(14) 0.41029(10) 0.45788(7) 0.0161(2) Uani 1 1 d . . . O4 O 0.06161(15) 0.53602(10) 0.37203(7) 0.0171(2) Uani 1 1 d . . . N1 N 0.33128(17) 0.67901(11) 0.35669(8) 0.0141(2) Uani 1 1 d . . . C1 C 0.2963(2) 0.78112(13) 0.37218(9) 0.0149(3) Uani 1 1 d . . . C2 C 0.2126(2) 0.81407(13) 0.43407(9) 0.0137(3) Uani 1 1 d . . . C3 C 0.1771(2) 0.73750(12) 0.48719(9) 0.0136(3) Uani 1 1 d . . . C4 C 0.1024(2) 0.77403(13) 0.54901(9) 0.0152(3) Uani 1 1 d . . . C5 C 0.0649(2) 0.88569(14) 0.55552(10) 0.0191(3) Uani 1 1 d . . . C6 C 0.0997(2) 0.96220(14) 0.50330(10) 0.0197(3) Uani 1 1 d . . . C7 C 0.1741(2) 0.92716(13) 0.44346(10) 0.0163(3) Uani 1 1 d . . . C8 C 0.0624(2) 0.69555(14) 0.60565(9) 0.0168(3) Uani 1 1 d . . . C9 C -0.0261(2) 0.59827(15) 0.59312(10) 0.0199(3) Uani 1 1 d . . . C10 C -0.0770(3) 0.53151(18) 0.64763(12) 0.0270(4) Uani 1 1 d . . . C11 C -0.0371(3) 0.5599(2) 0.71490(11) 0.0316(5) Uani 1 1 d . . . C12 C 0.0547(3) 0.6541(2) 0.72770(11) 0.0310(5) Uani 1 1 d . . . C13 C 0.1042(2) 0.72226(18) 0.67389(10) 0.0237(4) Uani 1 1 d . . . C14 C 0.4288(2) 0.65157(14) 0.29884(9) 0.0143(3) Uani 1 1 d . . . C15 C 0.4563(2) 0.53698(13) 0.29496(9) 0.0156(3) Uani 1 1 d . . . C16 C 0.5574(2) 0.49355(16) 0.24310(10) 0.0202(3) Uani 1 1 d . . . C17 C 0.6292(2) 0.56581(17) 0.19583(10) 0.0229(4) Uani 1 1 d . . . C18 C 0.6003(2) 0.67972(17) 0.19930(10) 0.0227(4) Uani 1 1 d . . . C19 C 0.5011(2) 0.72343(15) 0.25094(10) 0.0195(3) Uani 1 1 d . . . C20 C 0.1073(2) 0.32878(13) 0.46192(10) 0.0179(3) Uani 1 1 d . . . C21 C 0.1359(2) 0.24144(13) 0.40702(13) 0.0229(3) Uani 1 1 d . . . C22 C 0.1068(3) 0.28152(17) 0.53459(12) 0.0280(4) Uani 1 1 d . . . H1 H 0.325(3) 0.8367(19) 0.3426(13) 0.022(6) Uiso 1 1 d . . . H5 H 0.010(3) 0.9123(18) 0.5992(12) 0.015(5) Uiso 1 1 d . . . H6 H 0.067(3) 1.036(2) 0.5075(14) 0.028(7) Uiso 1 1 d . . . H7 H 0.196(3) 0.9757(19) 0.4116(17) 0.026(6) Uiso 1 1 d . . . H9 H -0.047(3) 0.5753(18) 0.5500(12) 0.012(5) Uiso 1 1 d . . . H10 H -0.135(3) 0.471(2) 0.6398(14) 0.027(7) Uiso 1 1 d . . . H11 H -0.072(3) 0.523(2) 0.7521(15) 0.029(7) Uiso 1 1 d . . . H12 H 0.079(3) 0.671(2) 0.7721(16) 0.037(8) Uiso 1 1 d . . . H13 H 0.164(4) 0.784(2) 0.6844(14) 0.033(7) Uiso 1 1 d . . . H16 H 0.583(3) 0.419(2) 0.2394(13) 0.021(6) Uiso 1 1 d . . . H17 H 0.690(4) 0.538(2) 0.1597(15) 0.030(7) Uiso 1 1 d . . . H18 H 0.647(3) 0.727(2) 0.1707(12) 0.023(6) Uiso 1 1 d . . . H19 H 0.486(4) 0.798(2) 0.2557(15) 0.041(7) Uiso 1 1 d . . . H20 H 0.000(3) 0.3693(18) 0.4510(12) 0.017(5) Uiso 1 1 d . . . H21A H 0.234(3) 0.201(2) 0.4197(14) 0.025(6) Uiso 1 1 d . . . H21B H 0.042(3) 0.1881(18) 0.4067(13) 0.020(5) Uiso 1 1 d . . . H21C H 0.143(3) 0.2742(19) 0.3626(13) 0.022(6) Uiso 1 1 d . . . H22A H 0.018(3) 0.228(2) 0.5406(14) 0.025(6) Uiso 1 1 d . . . H22B H 0.094(4) 0.338(3) 0.5686(17) 0.049(9) Uiso 1 1 d . . . H22C H 0.201(4) 0.243(2) 0.5436(16) 0.037(8) 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 0.01354(11) 0.01007(9) 0.01348(11) -0.00056(11) -0.00043(12) 0.00039(8) O1 0.0204(6) 0.0114(5) 0.0143(6) -0.0001(4) -0.0001(4) 0.0013(4) O2 0.0168(5) 0.0136(5) 0.0191(6) -0.0016(4) 0.0027(4) 0.0015(4) O3 0.0172(5) 0.0116(5) 0.0196(6) 0.0010(4) -0.0021(5) -0.0025(4) O4 0.0146(5) 0.0193(6) 0.0175(6) -0.0013(4) -0.0011(4) 0.0019(4) N1 0.0142(6) 0.0133(5) 0.0147(6) -0.0002(5) -0.0003(5) 0.0005(5) C1 0.0158(7) 0.0125(6) 0.0163(8) 0.0015(5) -0.0016(6) -0.0007(6) C2 0.0144(7) 0.0112(6) 0.0155(7) -0.0007(5) -0.0024(5) 0.0003(5) C3 0.0129(7) 0.0123(6) 0.0156(7) -0.0015(5) -0.0021(6) 0.0003(5) C4 0.0138(7) 0.0169(7) 0.0149(8) -0.0017(5) -0.0018(6) 0.0007(5) C5 0.0182(8) 0.0177(7) 0.0213(9) -0.0056(6) -0.0013(6) 0.0031(6) C6 0.0185(8) 0.0137(7) 0.0268(9) -0.0043(6) -0.0021(7) 0.0025(6) C7 0.0171(7) 0.0115(6) 0.0205(8) -0.0005(6) -0.0039(6) 0.0003(6) C8 0.0160(7) 0.0212(8) 0.0133(7) 0.0004(6) 0.0016(6) 0.0054(6) C9 0.0195(8) 0.0229(8) 0.0172(8) 0.0020(6) 0.0017(6) 0.0018(6) C10 0.0253(9) 0.0268(9) 0.0288(10) 0.0090(8) 0.0070(8) 0.0049(7) C11 0.0302(10) 0.0432(12) 0.0213(10) 0.0130(9) 0.0104(8) 0.0145(9) C12 0.0323(10) 0.0464(12) 0.0144(9) 0.0014(8) 0.0006(8) 0.0157(9) C13 0.0222(9) 0.0313(10) 0.0174(9) -0.0053(7) -0.0013(7) 0.0075(7) C14 0.0134(7) 0.0167(7) 0.0128(7) -0.0012(5) -0.0003(6) -0.0004(5) C15 0.0140(7) 0.0177(7) 0.0150(8) -0.0021(6) -0.0007(6) -0.0004(6) C16 0.0188(8) 0.0214(8) 0.0204(9) -0.0067(6) 0.0019(6) 0.0007(6) C17 0.0195(8) 0.0316(9) 0.0178(9) -0.0060(7) 0.0037(7) -0.0002(7) C18 0.0207(8) 0.0312(9) 0.0161(8) 0.0013(7) 0.0028(7) -0.0042(7) C19 0.0203(8) 0.0220(8) 0.0164(8) 0.0021(6) 0.0009(6) -0.0013(6) C20 0.0138(7) 0.0134(6) 0.0266(9) 0.0015(6) -0.0006(6) -0.0020(5) C21 0.0257(8) 0.0169(6) 0.0262(9) -0.0020(8) -0.0067(9) -0.0032(6) C22 0.0355(11) 0.0202(8) 0.0282(11) 0.0036(7) 0.0073(9) -0.0060(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 O4 1.5945(13) . ? V1 O3 1.7701(12) . ? V1 O1 1.8409(12) . ? V1 O2 1.8887(13) . ? V1 N1 2.1592(14) . ? O1 C3 1.3351(18) . ? O2 C15 1.342(2) . ? O3 C20 1.4384(19) . ? N1 C1 1.300(2) . ? N1 C14 1.411(2) . ? C1 C2 1.435(2) . ? C1 H1 0.91(2) . ? C2 C7 1.412(2) . ? C2 C3 1.413(2) . ? C3 C4 1.413(2) . ? C4 C5 1.388(2) . ? C4 C8 1.486(2) . ? C5 C6 1.399(3) . ? C5 H5 1.01(2) . ? C6 C7 1.374(3) . ? C6 H6 0.93(2) . ? C7 H7 0.87(3) . ? C8 C9 1.397(3) . ? C8 C13 1.403(2) . ? C9 C10 1.392(3) . ? C9 H9 0.90(2) . ? C10 C11 1.387(3) . ? C10 H10 0.88(3) . ? C11 C12 1.380(4) . ? C11 H11 0.89(3) . ? C12 C13 1.388(3) . ? C12 H12 0.91(3) . ? C13 H13 0.91(3) . ? C14 C19 1.399(2) . ? C14 C15 1.403(2) . ? C15 C16 1.399(2) . ? C16 C17 1.392(3) . ? C16 H16 0.93(3) . ? C17 C18 1.396(3) . ? C17 H17 0.92(3) . ? C18 C19 1.388(3) . ? C18 H18 0.88(2) . ? C19 H19 0.91(3) . ? C20 C21 1.516(3) . ? C20 C22 1.520(3) . ? C20 H20 1.02(2) . ? C21 H21A 0.97(3) . ? C21 H21B 1.00(2) . ? C21 H21C 0.95(2) . ? C22 H22A 0.97(3) . ? C22 H22B 0.95(3) . ? C22 H22C 0.91(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 O4 V1 O3 104.42(6) . . ? O4 V1 O1 105.01(6) . . ? O3 V1 O1 97.14(6) . . ? O4 V1 O2 106.76(6) . . ? O3 V1 O2 92.14(6) . . ? O1 V1 O2 143.41(6) . . ? O4 V1 N1 95.28(6) . . ? O3 V1 N1 159.67(6) . . ? O1 V1 N1 82.29(5) . . ? O2 V1 N1 77.19(5) . . ? C3 O1 V1 134.45(11) . . ? C15 O2 V1 121.08(10) . . ? C20 O3 V1 127.58(10) . . ? C1 N1 C14 121.88(14) . . ? C1 N1 V1 125.88(12) . . ? C14 N1 V1 112.09(10) . . ? N1 C1 C2 124.00(15) . . ? N1 C1 H1 119.7(15) . . ? C2 C1 H1 116.3(15) . . ? C7 C2 C3 119.57(16) . . ? C7 C2 C1 118.70(15) . . ? C3 C2 C1 121.61(14) . . ? O1 C3 C2 120.93(15) . . ? O1 C3 C4 118.94(15) . . ? C2 C3 C4 120.06(14) . . ? C5 C4 C3 118.30(16) . . ? C5 C4 C8 120.28(16) . . ? C3 C4 C8 121.41(14) . . ? C4 C5 C6 122.09(17) . . ? C4 C5 H5 118.8(13) . . ? C6 C5 H5 119.1(13) . . ? C7 C6 C5 119.74(15) . . ? C7 C6 H6 119.5(17) . . ? C5 C6 H6 120.7(17) . . ? C6 C7 C2 120.22(16) . . ? C6 C7 H7 118.9(18) . . ? C2 C7 H7 120.8(18) . . ? C9 C8 C13 118.74(17) . . ? C9 C8 C4 121.29(16) . . ? C13 C8 C4 119.84(17) . . ? C10 C9 C8 120.44(18) . . ? C10 C9 H9 118.3(14) . . ? C8 C9 H9 121.2(14) . . ? C11 C10 C9 120.1(2) . . ? C11 C10 H10 119.4(18) . . ? C9 C10 H10 120.5(19) . . ? C12 C11 C10 119.9(2) . . ? C12 C11 H11 115.7(18) . . ? C10 C11 H11 124.3(18) . . ? C11 C12 C13 120.6(2) . . ? C11 C12 H12 118.4(19) . . ? C13 C12 H12 120.9(19) . . ? C12 C13 C8 120.2(2) . . ? C12 C13 H13 118.1(18) . . ? C8 C13 H13 121.7(18) . . ? C19 C14 C15 120.62(16) . . ? C19 C14 N1 128.04(15) . . ? C15 C14 N1 111.27(14) . . ? O2 C15 C16 122.58(15) . . ? O2 C15 C14 117.30(14) . . ? C16 C15 C14 120.06(16) . . ? C17 C16 C15 118.86(17) . . ? C17 C16 H16 117.7(15) . . ? C15 C16 H16 123.4(15) . . ? C16 C17 C18 121.03(17) . . ? C16 C17 H17 119.9(16) . . ? C18 C17 H17 118.9(16) . . ? C19 C18 C17 120.39(18) . . ? C19 C18 H18 116.9(16) . . ? C17 C18 H18 122.7(16) . . ? C18 C19 C14 119.03(17) . . ? C18 C19 H19 121.8(19) . . ? C14 C19 H19 119.1(19) . . ? O3 C20 C21 109.07(14) . . ? O3 C20 C22 108.01(15) . . ? C21 C20 C22 112.97(15) . . ? O3 C20 H20 106.3(13) . . ? C21 C20 H20 108.5(13) . . ? C22 C20 H20 111.8(13) . . ? C20 C21 H21A 107.4(16) . . ? C20 C21 H21B 109.6(14) . . ? H21A C21 H21B 107.8(19) . . ? C20 C21 H21C 110.9(14) . . ? H21A C21 H21C 113(2) . . ? H21B C21 H21C 108(2) . . ? C20 C22 H22A 111.2(16) . . ? C20 C22 H22B 112.0(19) . . ? H22A C22 H22B 108(2) . . ? C20 C22 H22C 111.5(19) . . ? H22A C22 H22C 105(2) . . ? H22B C22 H22C 109(3) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 32.04 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.495 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.063 #===END data_plitt18 _database_code_depnum_ccdc_archive 'CCDC 233279' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H15 N2 O4 V, 0.5( C2 H6 O)' _chemical_formula_sum 'C20 H18 N2 O4.50 V' _chemical_formula_weight 409.30 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 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 15.3045(7) _cell_length_b 8.8087(4) _cell_length_c 13.3399(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.6870(10) _cell_angle_gamma 90.00 _cell_volume 1777.76(14) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.529 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 844 _exptl_absorpt_coefficient_mu 0.591 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8792 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(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 'CCD area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31681 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0159 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 32.02 _reflns_number_total 6133 _reflns_number_gt 5571 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Disorder of solvent molecule (ethanol), one hydrogen omitted. 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^)+(0.0491P)^2^+0.8266P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6133 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0363 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0912 _refine_ls_wR_factor_gt 0.0865 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 V1 V 0.051808(11) 0.763530(19) 0.406459(12) 0.01252(5) Uani 1 1 d . . . O1 O 0.16905(5) 0.68959(10) 0.45284(6) 0.02074(16) Uani 1 1 d . . . O2 O 0.01740(5) 0.65207(9) 0.31186(6) 0.01975(15) Uani 1 1 d . . . O3 O 0.08102(5) 0.92584(9) 0.36310(6) 0.01788(14) Uani 1 1 d . . . O4 O 0.30674(6) 0.83194(10) 0.40830(7) 0.02488(18) Uani 1 1 d . . . O5 O 0.41504(13) 1.0843(2) 0.41293(15) 0.0254(3) Uani 0.50 1 d P . . N1 N 0.02644(6) 0.69142(10) 0.55157(6) 0.01460(15) Uani 1 1 d . . . N2 N -0.07401(6) 0.85217(10) 0.41854(7) 0.01545(16) Uani 1 1 d . . . C1 C 0.08023(7) 0.62249(12) 0.62144(8) 0.01604(17) Uani 1 1 d . . . C2 C 0.16814(7) 0.57022(12) 0.61280(8) 0.01660(18) Uani 1 1 d . . . C3 C 0.20889(7) 0.60203(12) 0.52700(8) 0.01601(17) Uani 1 1 d . . . C4 C 0.29332(7) 0.54163(13) 0.51951(8) 0.01808(18) Uani 1 1 d . . . C5 C 0.33453(8) 0.45313(14) 0.60008(9) 0.0229(2) Uani 1 1 d . . . C6 C 0.29497(9) 0.42269(15) 0.68575(9) 0.0253(2) Uani 1 1 d . . . C7 C 0.21207(8) 0.48085(14) 0.69208(8) 0.0217(2) Uani 1 1 d . . . C8 C 0.33724(7) 0.56168(13) 0.42809(8) 0.01832(19) Uani 1 1 d . . . C9 C 0.34300(7) 0.70092(13) 0.37782(9) 0.01951(19) Uani 1 1 d . . . C10 C 0.39017(8) 0.71244(15) 0.29631(10) 0.0234(2) Uani 1 1 d . . . C11 C 0.43211(8) 0.58597(16) 0.26326(10) 0.0255(2) Uani 1 1 d . . . C12 C 0.42559(8) 0.44688(15) 0.31027(10) 0.0256(2) Uani 1 1 d . . . C13 C 0.37873(7) 0.43573(14) 0.39138(9) 0.0222(2) Uani 1 1 d . . . C14 C -0.06199(7) 0.72194(13) 0.57838(8) 0.01685(18) Uani 1 1 d . . . C15 C -0.11545(7) 0.81124(12) 0.49584(8) 0.01574(17) Uani 1 1 d . . . C16 C -0.11604(7) 0.94224(13) 0.34406(9) 0.01977(19) Uani 1 1 d . . . C17 C -0.20172(8) 0.99087(15) 0.34414(9) 0.0231(2) Uani 1 1 d . . . C18 C -0.24577(8) 0.94561(16) 0.42347(9) 0.0249(2) Uani 1 1 d . . . C19 C -0.20241(7) 0.85549(15) 0.50002(8) 0.0218(2) Uani 1 1 d . . . C20 C 0.47810(10) 1.07719(16) 0.49215(11) 0.0313(3) Uani 1 1 d . . . H4O H 0.2570(15) 0.807(3) 0.4235(16) 0.043(5) Uiso 1 1 d . . . H5 H 0.3918(13) 0.417(2) 0.5972(14) 0.033(5) Uiso 1 1 d . . . H6 H 0.3268(12) 0.359(2) 0.7410(13) 0.029(4) Uiso 1 1 d . . . H7 H 0.1840(12) 0.464(2) 0.7501(14) 0.030(4) Uiso 1 1 d . . . H8 H 0.0601(11) 0.600(2) 0.6833(13) 0.022(4) Uiso 1 1 d . . . H10 H 0.3926(13) 0.809(2) 0.2632(15) 0.035(5) Uiso 1 1 d . . . H11 H 0.4632(12) 0.596(2) 0.2078(13) 0.027(4) Uiso 1 1 d . . . H12 H 0.4523(13) 0.361(2) 0.2845(14) 0.033(5) Uiso 1 1 d . . . H13 H 0.3754(11) 0.342(2) 0.4229(13) 0.025(4) Uiso 1 1 d . . . H14A H -0.0566(12) 0.7772(19) 0.6412(14) 0.022(4) Uiso 1 1 d . . . H14B H -0.0910(11) 0.6238(19) 0.5897(12) 0.022(4) Uiso 1 1 d . . . H16 H -0.0840(12) 0.969(2) 0.2926(13) 0.025(4) Uiso 1 1 d . . . H17 H -0.2285(12) 1.053(2) 0.2899(13) 0.027(4) Uiso 1 1 d . . . H18 H -0.3080(14) 0.974(2) 0.4248(16) 0.042(5) Uiso 1 1 d . . . H19 H -0.2299(12) 0.824(2) 0.5555(13) 0.025(4) Uiso 1 1 d . . . H5O H 0.391(2) 1.026(4) 0.420(3) 0.020(8) Uiso 0.50 1 d P . . H20A H 0.4571(13) 1.109(2) 0.5578(16) 0.040(5) Uiso 1 1 d . . . H20B H 0.5210(14) 1.153(2) 0.4747(15) 0.043(5) 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 0.01357(8) 0.01275(8) 0.01156(8) 0.00016(5) 0.00290(6) 0.00018(5) O1 0.0162(3) 0.0269(4) 0.0197(4) 0.0086(3) 0.0049(3) 0.0046(3) O2 0.0215(4) 0.0195(4) 0.0187(3) -0.0056(3) 0.0043(3) -0.0008(3) O3 0.0183(3) 0.0156(3) 0.0203(4) 0.0025(3) 0.0047(3) -0.0008(3) O4 0.0228(4) 0.0188(4) 0.0358(5) -0.0033(3) 0.0135(3) -0.0014(3) O5 0.0254(8) 0.0196(8) 0.0295(9) 0.0018(7) -0.0014(7) -0.0048(7) N1 0.0152(4) 0.0157(4) 0.0132(4) -0.0007(3) 0.0035(3) -0.0010(3) N2 0.0155(4) 0.0161(4) 0.0149(4) -0.0007(3) 0.0031(3) 0.0007(3) C1 0.0190(4) 0.0158(4) 0.0134(4) -0.0003(3) 0.0025(3) -0.0014(3) C2 0.0182(4) 0.0170(4) 0.0143(4) 0.0001(3) 0.0014(3) 0.0007(3) C3 0.0157(4) 0.0165(4) 0.0153(4) 0.0003(3) 0.0006(3) 0.0006(3) C4 0.0155(4) 0.0191(5) 0.0189(4) -0.0017(4) 0.0003(3) 0.0012(3) C5 0.0201(5) 0.0257(5) 0.0214(5) -0.0017(4) -0.0019(4) 0.0059(4) C6 0.0274(5) 0.0277(6) 0.0188(5) 0.0020(4) -0.0026(4) 0.0078(4) C7 0.0259(5) 0.0229(5) 0.0156(4) 0.0017(4) 0.0006(4) 0.0039(4) C8 0.0134(4) 0.0205(5) 0.0207(5) -0.0034(4) 0.0012(3) 0.0003(3) C9 0.0151(4) 0.0202(5) 0.0237(5) -0.0045(4) 0.0046(4) -0.0017(4) C10 0.0194(5) 0.0252(5) 0.0272(5) -0.0028(4) 0.0083(4) -0.0035(4) C11 0.0187(5) 0.0317(6) 0.0278(6) -0.0079(5) 0.0087(4) -0.0039(4) C12 0.0184(5) 0.0274(6) 0.0319(6) -0.0092(5) 0.0068(4) 0.0011(4) C13 0.0176(4) 0.0217(5) 0.0274(5) -0.0038(4) 0.0035(4) 0.0018(4) C14 0.0163(4) 0.0210(5) 0.0140(4) -0.0001(3) 0.0046(3) -0.0006(3) C15 0.0151(4) 0.0182(4) 0.0141(4) -0.0034(3) 0.0027(3) -0.0012(3) C16 0.0189(4) 0.0211(5) 0.0194(5) 0.0026(4) 0.0032(4) 0.0034(4) C17 0.0194(5) 0.0266(5) 0.0225(5) 0.0002(4) 0.0007(4) 0.0057(4) C18 0.0163(4) 0.0352(6) 0.0229(5) -0.0049(4) 0.0023(4) 0.0045(4) C19 0.0152(4) 0.0327(6) 0.0179(5) -0.0049(4) 0.0036(4) 0.0005(4) C20 0.0343(7) 0.0281(6) 0.0322(6) 0.0049(5) 0.0070(5) 0.0054(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 V1 O2 1.6227(8) . ? V1 O3 1.6300(8) . ? V1 O1 1.9212(8) . ? V1 N2 2.1065(9) . ? V1 N1 2.1280(9) . ? O1 C3 1.3279(13) . ? O4 C9 1.3687(14) . ? O4 H4O 0.85(2) . ? O5 C20 1.321(2) . ? O5 H5O 0.65(4) . ? N1 C1 1.2974(13) . ? N1 C14 1.4759(13) . ? N2 C15 1.3390(13) . ? N2 C16 1.3555(14) . ? C1 C2 1.4430(15) . ? C1 H8 0.944(17) . ? C2 C7 1.4054(15) . ? C2 C3 1.4118(14) . ? C3 C4 1.4148(14) . ? C4 C5 1.3985(16) . ? C4 C8 1.4892(15) . ? C5 C6 1.3977(18) . ? C5 H5 0.940(19) . ? C6 C7 1.3826(17) . ? C6 H6 0.994(18) . ? C7 H7 0.953(18) . ? C8 C13 1.4028(15) . ? C8 C9 1.4071(16) . ? C9 C10 1.3967(16) . ? C10 C11 1.3903(18) . ? C10 H10 0.96(2) . ? C11 C12 1.3868(19) . ? C11 H11 0.943(18) . ? C12 C13 1.3890(17) . ? C12 H12 0.95(2) . ? C13 H13 0.928(18) . ? C14 C15 1.4928(15) . ? C14 H14A 0.962(18) . ? C14 H14B 0.993(17) . ? C15 C19 1.3959(15) . ? C16 C17 1.3797(15) . ? C16 H16 0.932(17) . ? C17 C18 1.3961(17) . ? C17 H17 0.951(18) . ? C18 C19 1.3816(17) . ? C18 H18 0.99(2) . ? C19 H19 0.947(18) . ? C20 C20 1.517(3) 3_676 ? C20 H20A 1.02(2) . ? C20 H20B 0.99(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 O2 V1 O3 109.21(4) . . ? O2 V1 O1 102.88(4) . . ? O3 V1 O1 96.82(4) . . ? O2 V1 N2 95.21(4) . . ? O3 V1 N2 90.28(4) . . ? O1 V1 N2 157.08(4) . . ? O2 V1 N1 116.39(4) . . ? O3 V1 N1 133.01(4) . . ? O1 V1 N1 84.01(3) . . ? N2 V1 N1 75.32(3) . . ? C3 O1 V1 137.59(7) . . ? C9 O4 H4O 106.0(15) . . ? C20 O5 H5O 102(3) . . ? C1 N1 C14 114.63(8) . . ? C1 N1 V1 127.59(7) . . ? C14 N1 V1 117.78(7) . . ? C15 N2 C16 119.65(9) . . ? C15 N2 V1 120.26(7) . . ? C16 N2 V1 119.92(7) . . ? N1 C1 C2 126.16(9) . . ? N1 C1 H8 118.1(10) . . ? C2 C1 H8 115.7(10) . . ? C7 C2 C3 120.10(10) . . ? C7 C2 C1 117.67(9) . . ? C3 C2 C1 122.19(9) . . ? O1 C3 C2 120.66(9) . . ? O1 C3 C4 119.17(9) . . ? C2 C3 C4 120.17(9) . . ? C5 C4 C3 117.78(10) . . ? C5 C4 C8 119.24(10) . . ? C3 C4 C8 122.90(10) . . ? C6 C5 C4 122.31(11) . . ? C6 C5 H5 119.3(11) . . ? C4 C5 H5 118.3(11) . . ? C7 C6 C5 119.58(11) . . ? C7 C6 H6 121.0(10) . . ? C5 C6 H6 119.4(10) . . ? C6 C7 C2 120.04(11) . . ? C6 C7 H7 121.4(11) . . ? C2 C7 H7 118.5(11) . . ? C13 C8 C9 117.31(10) . . ? C13 C8 C4 118.44(10) . . ? C9 C8 C4 124.21(10) . . ? O4 C9 C10 116.77(11) . . ? O4 C9 C8 122.41(10) . . ? C10 C9 C8 120.75(10) . . ? C11 C10 C9 120.42(12) . . ? C11 C10 H10 120.8(12) . . ? C9 C10 H10 118.8(12) . . ? C12 C11 C10 119.76(11) . . ? C12 C11 H11 120.9(11) . . ? C10 C11 H11 119.3(11) . . ? C11 C12 C13 119.71(11) . . ? C11 C12 H12 118.4(12) . . ? C13 C12 H12 121.9(12) . . ? C12 C13 C8 122.02(12) . . ? C12 C13 H13 119.1(11) . . ? C8 C13 H13 118.9(11) . . ? N1 C14 C15 109.73(8) . . ? N1 C14 H14A 110.0(11) . . ? C15 C14 H14A 110.0(10) . . ? N1 C14 H14B 109.0(10) . . ? C15 C14 H14B 111.3(10) . . ? H14A C14 H14B 106.8(14) . . ? N2 C15 C19 121.39(10) . . ? N2 C15 C14 116.06(9) . . ? C19 C15 C14 122.49(9) . . ? N2 C16 C17 121.80(10) . . ? N2 C16 H16 116.3(11) . . ? C17 C16 H16 121.9(11) . . ? C16 C17 C18 118.67(11) . . ? C16 C17 H17 118.7(11) . . ? C18 C17 H17 122.6(11) . . ? C19 C18 C17 119.43(10) . . ? C19 C18 H18 119.3(12) . . ? C17 C18 H18 121.3(12) . . ? C18 C19 C15 119.04(10) . . ? C18 C19 H19 121.7(11) . . ? C15 C19 H19 119.3(11) . . ? O5 C20 C20 114.05(18) . 3_676 ? O5 C20 H20A 112.9(12) . . ? C20 C20 H20A 108.4(12) 3_676 . ? O5 C20 H20B 102.2(12) . . ? C20 C20 H20B 109.9(12) 3_676 . ? H20A C20 H20B 109.2(17) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 32.02 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.610 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.075 #===END