# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Ebbe Nordlander' _publ_contact_author_email EBBE.NORDLANDER@CHEMPHYS.LU.SE _publ_section_title ; Bis- and tris(pyridyl)amine-oxidovanadium complexes: Characteristics and insulin-mimetic potential ; loop_ _publ_author_name 'Ebbe Nordlander' 'Eva Degerman' 'Eva Anna Enyedy' 'Hossein Esbak' 'Eugenio Garribba' ; M.Haukka ; 'T. Kiss' 'George C. Lisensky' 'Jessica Nilsson' 'Dieter Rehder' 'Hiromu Sakurai' 'Yutaka Yoshikawa' # Attachment 'jn1042ds.cif' data_jn1042ds _database_code_depnum_ccdc_archive 'CCDC 688673' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H19 N3 O6 S V' _chemical_formula_sum 'C19 H19 N3 O6 S V' _chemical_formula_weight 468.37 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' S S 0.1246 0.1234 '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 'P 21/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 17.7424(4) _cell_length_b 7.8207(3) _cell_length_c 14.2763(6) _cell_angle_alpha 90.00 _cell_angle_beta 103.265(3) _cell_angle_gamma 90.00 _cell_volume 1928.10(12) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6436 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 28.70 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.614 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 964 _exptl_absorpt_coefficient_mu 0.667 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8737 _exptl_absorpt_correction_T_max 0.9002 _exptl_absorpt_process_details 'SADABS v.2.10 (Sheldrick, 2003)' _publ_section_exptl_refinement ; The OH hydrogen was located from the difference Fourier map but constrained to ride on its parent atom, with U~iso~ = 1.5 U~eq~(parent atom). Other hydrogens were positioned geometrically and were also constrained to ride on their parent atoms, with C---H =0.95-0.99 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20463 _diffrn_reflns_av_R_equivalents 0.0524 _diffrn_reflns_av_sigmaI/netI 0.0623 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 28.72 _reflns_number_total 4975 _reflns_number_gt 3392 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond v.3.1c (Crystal Impact GbR, 2006)' _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^)+(0.0417P)^2^+0.7456P] 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 4975 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0777 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.0953 _refine_ls_wR_factor_gt 0.0832 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 0.22495(2) 0.58303(5) 0.13983(2) 0.01640(11) Uani 1 1 d . . . S1 S 0.16567(3) 0.39082(7) 0.31441(4) 0.01985(14) Uani 1 1 d . . . O1 O 0.24220(9) 0.4336(2) 0.07093(10) 0.0229(3) Uani 1 1 d . . . O2 O 0.31026(8) 0.57449(19) 0.25577(10) 0.0187(3) Uani 1 1 d . . . O3 O 0.15702(8) 0.4713(2) 0.21736(10) 0.0214(3) Uani 1 1 d . . . O4 O 0.14511(10) 0.5099(2) 0.38078(11) 0.0315(4) Uani 1 1 d . . . O5 O 0.25372(9) 0.3499(2) 0.34734(11) 0.0280(4) Uani 1 1 d . . . H5O H 0.2864 0.4281 0.3233 0.042 Uiso 1 1 d R . . O6 O 0.12590(9) 0.2297(2) 0.30629(11) 0.0268(4) Uani 1 1 d . . . N1 N 0.19253(9) 0.8429(2) 0.19508(11) 0.0163(4) Uani 1 1 d . . . N2 N 0.11884(9) 0.6583(2) 0.04833(11) 0.0166(4) Uani 1 1 d . . . N3 N 0.29164(9) 0.7643(2) 0.08394(11) 0.0174(4) Uani 1 1 d . . . C1 C 0.10722(11) 0.8353(3) 0.18370(14) 0.0181(4) Uani 1 1 d . . . H1A H 0.0865 0.9511 0.1904 0.022 Uiso 1 1 calc R . . H1B H 0.0943 0.7607 0.2338 0.022 Uiso 1 1 calc R . . C2 C 0.07223(11) 0.7644(3) 0.08514(14) 0.0171(4) Uani 1 1 d . . . C3 C -0.00200(12) 0.8021(3) 0.03448(15) 0.0202(5) Uani 1 1 d . . . H3 H -0.0343 0.8745 0.0616 0.024 Uiso 1 1 calc R . . C4 C -0.02874(12) 0.7330(3) -0.05653(15) 0.0220(5) Uani 1 1 d . . . H4 H -0.0799 0.7567 -0.0920 0.026 Uiso 1 1 calc R . . C5 C 0.01953(12) 0.6290(3) -0.09550(15) 0.0211(5) Uani 1 1 d . . . H5 H 0.0028 0.5836 -0.1586 0.025 Uiso 1 1 calc R . . C6 C 0.09252(12) 0.5928(3) -0.04040(14) 0.0184(4) Uani 1 1 d . . . H6 H 0.1253 0.5192 -0.0660 0.022 Uiso 1 1 calc R . . C7 C 0.21223(12) 0.9813(3) 0.13326(14) 0.0178(4) Uani 1 1 d . . . H7A H 0.2230 1.0883 0.1710 0.021 Uiso 1 1 calc R . . H7B H 0.1677 1.0021 0.0784 0.021 Uiso 1 1 calc R . . C8 C 0.28181(11) 0.9327(3) 0.09610(13) 0.0168(4) Uani 1 1 d . . . C9 C 0.33088(12) 1.0547(3) 0.07178(14) 0.0216(5) Uani 1 1 d . . . H9 H 0.3225 1.1731 0.0804 0.026 Uiso 1 1 calc R . . C10 C 0.39238(13) 1.0000(3) 0.03472(15) 0.0252(5) Uani 1 1 d . . . H10 H 0.4267 1.0809 0.0173 0.030 Uiso 1 1 calc R . . C11 C 0.40342(12) 0.8270(3) 0.02325(14) 0.0237(5) Uani 1 1 d . . . H11 H 0.4456 0.7873 -0.0015 0.028 Uiso 1 1 calc R . . C12 C 0.35226(11) 0.7133(3) 0.04835(14) 0.0200(5) Uani 1 1 d . . . H12 H 0.3598 0.5945 0.0404 0.024 Uiso 1 1 calc R . . C13 C 0.23344(12) 0.8701(3) 0.29800(14) 0.0187(5) Uani 1 1 d . . . H13A H 0.2173 0.7806 0.3384 0.022 Uiso 1 1 calc R . . H13B H 0.2184 0.9825 0.3199 0.022 Uiso 1 1 calc R . . C14 C 0.32019(12) 0.8640(3) 0.31058(13) 0.0182(5) Uani 1 1 d . . . C15 C 0.36672(13) 1.0047(3) 0.34322(14) 0.0228(5) Uani 1 1 d . . . H15 H 0.3437 1.1073 0.3587 0.027 Uiso 1 1 calc R . . C16 C 0.44648(13) 0.9974(3) 0.35356(15) 0.0275(5) Uani 1 1 d . . . H16 H 0.4777 1.0944 0.3759 0.033 Uiso 1 1 calc R . . C17 C 0.48026(13) 0.8474(3) 0.33103(15) 0.0261(5) Uani 1 1 d . . . H17 H 0.5347 0.8421 0.3377 0.031 Uiso 1 1 calc R . . C18 C 0.43501(12) 0.7054(3) 0.29891(14) 0.0220(5) Uani 1 1 d . . . H18 H 0.4584 0.6028 0.2839 0.026 Uiso 1 1 calc R . . C19 C 0.35492(12) 0.7132(3) 0.28861(14) 0.0184(5) 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 V1 0.01735(19) 0.0152(2) 0.01694(18) -0.00112(14) 0.00452(13) 0.00101(15) S1 0.0233(3) 0.0175(3) 0.0193(3) 0.0010(2) 0.0060(2) -0.0007(2) O1 0.0255(8) 0.0195(9) 0.0241(8) -0.0045(6) 0.0064(6) 0.0023(7) O2 0.0183(7) 0.0158(8) 0.0204(7) 0.0003(6) 0.0013(6) -0.0006(6) O3 0.0198(8) 0.0235(9) 0.0204(7) 0.0051(6) 0.0037(6) -0.0023(7) O4 0.0450(10) 0.0250(9) 0.0295(8) -0.0063(7) 0.0188(7) -0.0038(8) O5 0.0234(8) 0.0297(10) 0.0290(8) 0.0100(7) 0.0020(6) -0.0004(7) O6 0.0319(9) 0.0180(9) 0.0303(8) 0.0024(7) 0.0068(7) -0.0060(7) N1 0.0152(9) 0.0178(10) 0.0169(8) 0.0002(7) 0.0053(7) 0.0003(7) N2 0.0182(9) 0.0148(9) 0.0181(8) 0.0013(7) 0.0066(7) -0.0022(7) N3 0.0173(9) 0.0202(10) 0.0146(8) -0.0001(7) 0.0034(7) 0.0022(8) C1 0.0161(10) 0.0181(12) 0.0217(10) -0.0022(9) 0.0077(8) 0.0004(9) C2 0.0174(11) 0.0132(11) 0.0221(10) 0.0026(9) 0.0073(8) -0.0020(9) C3 0.0173(11) 0.0168(12) 0.0272(11) 0.0029(9) 0.0066(9) -0.0008(9) C4 0.0195(11) 0.0189(12) 0.0256(11) 0.0052(9) 0.0008(9) -0.0026(9) C5 0.0220(11) 0.0212(13) 0.0192(10) 0.0030(9) 0.0027(8) -0.0050(9) C6 0.0210(11) 0.0183(12) 0.0174(10) 0.0003(9) 0.0075(8) -0.0032(9) C7 0.0196(11) 0.0136(11) 0.0206(10) 0.0014(9) 0.0057(8) 0.0012(9) C8 0.0156(10) 0.0203(12) 0.0131(9) 0.0022(8) 0.0003(7) 0.0012(9) C9 0.0218(11) 0.0209(13) 0.0218(11) 0.0033(9) 0.0046(9) -0.0021(9) C10 0.0226(12) 0.0307(14) 0.0234(11) 0.0044(10) 0.0074(9) -0.0047(10) C11 0.0172(11) 0.0371(15) 0.0174(10) 0.0016(10) 0.0053(8) 0.0046(10) C12 0.0194(11) 0.0243(12) 0.0162(10) 0.0002(9) 0.0043(8) 0.0047(9) C13 0.0225(11) 0.0181(12) 0.0162(10) -0.0026(9) 0.0057(8) 0.0003(9) C14 0.0206(11) 0.0211(12) 0.0126(9) 0.0008(9) 0.0032(8) -0.0007(9) C15 0.0286(13) 0.0199(13) 0.0189(10) -0.0018(9) 0.0032(9) -0.0007(10) C16 0.0274(13) 0.0292(14) 0.0244(11) -0.0019(10) 0.0028(9) -0.0115(11) C17 0.0204(11) 0.0339(14) 0.0238(11) 0.0031(10) 0.0046(9) -0.0035(10) C18 0.0210(11) 0.0266(13) 0.0184(10) 0.0014(9) 0.0044(8) 0.0030(10) C19 0.0211(11) 0.0205(12) 0.0131(9) 0.0016(8) 0.0031(8) -0.0015(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag V1 O1 1.6015(15) . ? V1 O2 1.9711(14) . ? V1 O3 2.0132(14) . ? V1 N2 2.1139(17) . ? V1 N3 2.1166(17) . ? V1 N1 2.3001(18) . ? S1 O4 1.4341(16) . ? S1 O6 1.4360(16) . ? S1 O3 1.4974(15) . ? S1 O5 1.5579(16) . ? O2 C19 1.362(3) . ? O5 H5O 0.9591 . ? N1 C1 1.486(2) . ? N1 C7 1.488(3) . ? N1 C13 1.497(2) . ? N2 C6 1.347(3) . ? N2 C2 1.360(3) . ? N3 C8 1.345(3) . ? N3 C12 1.351(2) . ? C1 C2 1.507(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.381(3) . ? C3 C4 1.387(3) . ? C3 H3 0.9500 . ? C4 C5 1.387(3) . ? C4 H4 0.9500 . ? C5 C6 1.381(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.500(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.389(3) . ? C9 C10 1.385(3) . ? C9 H9 0.9500 . ? C10 C11 1.383(3) . ? C10 H10 0.9500 . ? C11 C12 1.375(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.509(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.390(3) . ? C14 C19 1.399(3) . ? C15 C16 1.390(3) . ? C15 H15 0.9500 . ? C16 C17 1.388(3) . ? C16 H16 0.9500 . ? C17 C18 1.386(3) . ? C17 H17 0.9500 . ? C18 C19 1.396(3) . ? C18 H18 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 V1 O2 105.84(7) . . ? O1 V1 O3 104.12(7) . . ? O2 V1 O3 87.99(6) . . ? O1 V1 N2 95.28(7) . . ? O2 V1 N2 158.71(6) . . ? O3 V1 N2 84.25(6) . . ? O1 V1 N3 93.16(7) . . ? O2 V1 N3 87.21(6) . . ? O3 V1 N3 162.72(7) . . ? N2 V1 N3 94.37(6) . . ? O1 V1 N1 162.42(7) . . ? O2 V1 N1 86.92(6) . . ? O3 V1 N1 88.08(6) . . ? N2 V1 N1 73.06(6) . . ? N3 V1 N1 75.10(6) . . ? O4 S1 O6 115.37(9) . . ? O4 S1 O3 110.53(10) . . ? O6 S1 O3 110.49(9) . . ? O4 S1 O5 108.88(10) . . ? O6 S1 O5 106.51(9) . . ? O3 S1 O5 104.39(8) . . ? C19 O2 V1 122.43(12) . . ? S1 O3 V1 138.07(9) . . ? S1 O5 H5O 114.1 . . ? C1 N1 C7 109.65(16) . . ? C1 N1 C13 111.42(14) . . ? C7 N1 C13 110.58(16) . . ? C1 N1 V1 104.83(12) . . ? C7 N1 V1 109.16(11) . . ? C13 N1 V1 111.04(12) . . ? C6 N2 C2 119.03(17) . . ? C6 N2 V1 122.89(14) . . ? C2 N2 V1 117.74(13) . . ? C8 N3 C12 118.40(18) . . ? C8 N3 V1 120.47(13) . . ? C12 N3 V1 120.42(15) . . ? N1 C1 C2 107.92(15) . . ? N1 C1 H1A 110.1 . . ? C2 C1 H1A 110.1 . . ? N1 C1 H1B 110.1 . . ? C2 C1 H1B 110.1 . . ? H1A C1 H1B 108.4 . . ? N2 C2 C3 121.29(19) . . ? N2 C2 C1 115.38(17) . . ? C3 C2 C1 123.32(19) . . ? C2 C3 C4 119.2(2) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C3 C4 C5 119.6(2) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C6 C5 C4 118.4(2) . . ? C6 C5 H5 120.8 . . ? C4 C5 H5 120.8 . . ? N2 C6 C5 122.4(2) . . ? N2 C6 H6 118.8 . . ? C5 C6 H6 118.8 . . ? N1 C7 C8 110.48(17) . . ? N1 C7 H7A 109.6 . . ? C8 C7 H7A 109.6 . . ? N1 C7 H7B 109.6 . . ? C8 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? N3 C8 C9 122.24(19) . . ? N3 C8 C7 115.80(18) . . ? C9 C8 C7 121.9(2) . . ? C10 C9 C8 118.5(2) . . ? C10 C9 H9 120.7 . . ? C8 C9 H9 120.7 . . ? C11 C10 C9 119.5(2) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C12 C11 C10 118.8(2) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? N3 C12 C11 122.5(2) . . ? N3 C12 H12 118.7 . . ? C11 C12 H12 118.7 . . ? N1 C13 C14 111.34(15) . . ? N1 C13 H13A 109.4 . . ? C14 C13 H13A 109.4 . . ? N1 C13 H13B 109.4 . . ? C14 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? C15 C14 C19 118.94(19) . . ? C15 C14 C13 121.7(2) . . ? C19 C14 C13 119.31(19) . . ? C14 C15 C16 121.0(2) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C17 C16 C15 119.6(2) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C18 C17 C16 120.4(2) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C17 C18 C19 119.9(2) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? O2 C19 C18 119.9(2) . . ? O2 C19 C14 119.82(18) . . ? C18 C19 C14 120.2(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5O O2 0.96 1.61 2.531(2) 158.3 . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.72 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.401 _refine_diff_density_min -0.442 _refine_diff_density_rms 0.075 # Attachment 'jn1046d.cif' data_jn1046d _database_code_depnum_ccdc_archive 'CCDC 711845' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H19 Cl2 N3 O2 V, C H4 O' _chemical_formula_sum 'C20 H23 Cl2 N3 O3 V' _chemical_formula_weight 475.25 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' Cl Cl 0.1484 0.1585 '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 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.2798(4) _cell_length_b 14.8063(6) _cell_length_c 17.2853(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2119.06(16) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6610 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour 'pale green' _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 980 _exptl_absorpt_coefficient_mu 0.747 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8836 _exptl_absorpt_correction_T_max 0.9636 _exptl_absorpt_process_details 'Xprep in Shelxtl v.6.14-1 (Sheldrick, 2005)' _publ_section_exptl_refinement ; The OH hydrogens were located from the difference Fourier map but constrained to ride on their parent atom, with U~iso~ = 1.5 U~eq~(parent atom). Other hydrogens were positioned geometrically and were also constrained to ride on their parent atoms, with C---H =0.98-0.99 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18593 _diffrn_reflns_av_R_equivalents 0.0508 _diffrn_reflns_av_sigmaI/netI 0.0547 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 27.45 _reflns_number_total 4826 _reflns_number_gt 3897 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond v.3.1d (Brandenburg, 2006)' _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^)+(0.0339P)^2^+0.2772P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _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 -0.02(2) _chemical_absolute_configuration unk _refine_ls_number_reflns 4826 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0550 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0788 _refine_ls_wR_factor_gt 0.0721 _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 V1 V 0.45022(6) 0.97751(3) 0.06544(2) 0.02199(11) Uani 1 1 d . . . Cl1 Cl 0.44041(10) 0.87405(4) 0.16873(4) 0.02975(16) Uani 1 1 d . . . Cl2 Cl 0.64656(9) 1.06554(4) 0.12704(4) 0.02936(16) Uani 1 1 d . . . O1 O 0.5563(2) 0.92310(11) 0.00365(10) 0.0281(4) Uani 1 1 d . . . O2 O -0.0594(3) 1.02240(12) 0.26018(10) 0.0310(4) Uani 1 1 d . . . H2O H -0.1586 1.0118 0.2726 0.046 Uiso 1 1 d R . . O3 O 0.6378(3) 0.97920(16) 0.30159(12) 0.0445(5) Uani 1 1 d . . . H3O H 0.6070 0.9574 0.2524 0.091(15) Uiso 1 1 d R . . N1 N 0.2520(3) 1.07090(13) 0.12496(12) 0.0200(5) Uani 1 1 d . . . N2 N 0.4042(3) 1.08643(14) -0.01205(12) 0.0246(5) Uani 1 1 d . . . N3 N 0.2287(3) 0.92512(13) 0.02439(12) 0.0206(5) Uani 1 1 d . . . C1 C 0.2559(3) 1.06555(17) 0.21140(14) 0.0226(5) Uani 1 1 d . . . H1A H 0.3686 1.0754 0.2287 0.027 Uiso 1 1 calc R . . H1B H 0.2249 1.0036 0.2269 0.027 Uiso 1 1 calc R . . C2 C 0.1482(3) 1.13160(16) 0.25397(14) 0.0215(5) Uani 1 1 d . . . C3 C -0.0085(3) 1.10857(17) 0.27552(14) 0.0244(6) Uani 1 1 d . . . C4 C -0.1059(3) 1.17051(19) 0.31324(15) 0.0294(7) Uani 1 1 d . . . H4 H -0.2134 1.1546 0.3267 0.035 Uiso 1 1 calc R . . C5 C -0.0478(4) 1.25488(18) 0.33126(14) 0.0324(7) Uani 1 1 d . . . H5 H -0.1162 1.2973 0.3563 0.039 Uiso 1 1 calc R . . C6 C 0.1105(4) 1.27873(19) 0.31319(15) 0.0320(7) Uani 1 1 d . . . H6 H 0.1520 1.3363 0.3272 0.038 Uiso 1 1 calc R . . C7 C 0.2061(3) 1.21669(17) 0.27431(15) 0.0270(6) Uani 1 1 d . . . H7 H 0.3138 1.2326 0.2612 0.032 Uiso 1 1 calc R . . C8 C 0.2938(3) 1.16334(16) 0.09835(15) 0.0246(6) Uani 1 1 d . . . H8A H 0.3895 1.1856 0.1269 0.030 Uiso 1 1 calc R . . H8B H 0.2026 1.2049 0.1088 0.030 Uiso 1 1 calc R . . C9 C 0.3291(3) 1.16156(17) 0.01343(15) 0.0241(6) Uani 1 1 d . . . C10 C 0.4391(4) 1.07938(17) -0.08806(14) 0.0305(6) Uani 1 1 d . . . H10 H 0.4900 1.0259 -0.1063 0.037 Uiso 1 1 calc R . . C11 C 0.4038(4) 1.14659(19) -0.13999(17) 0.0363(7) Uani 1 1 d . . . H11 H 0.4304 1.1399 -0.1931 0.044 Uiso 1 1 calc R . . C12 C 0.3287(4) 1.2242(2) -0.11370(16) 0.0372(7) Uani 1 1 d . . . H12 H 0.3034 1.2718 -0.1486 0.045 Uiso 1 1 calc R . . C13 C 0.2907(4) 1.23180(19) -0.03592(17) 0.0340(7) Uani 1 1 d . . . H13 H 0.2390 1.2845 -0.0168 0.041 Uiso 1 1 calc R . . C14 C 0.0892(3) 1.04652(17) 0.09379(15) 0.0264(6) Uani 1 1 d . . . H14A H 0.0490 1.0973 0.0619 0.032 Uiso 1 1 calc R . . H14B H 0.0137 1.0387 0.1377 0.032 Uiso 1 1 calc R . . C15 C 0.0874(3) 0.96190(16) 0.04566(13) 0.0208(6) Uani 1 1 d . . . C16 C 0.2260(3) 0.85223(16) -0.02234(15) 0.0249(6) Uani 1 1 d . . . H16 H 0.3256 0.8265 -0.0383 0.030 Uiso 1 1 calc R . . C17 C 0.0846(4) 0.81371(18) -0.04779(16) 0.0306(6) Uani 1 1 d . . . H17 H 0.0866 0.7621 -0.0804 0.037 Uiso 1 1 calc R . . C18 C -0.0598(4) 0.85131(17) -0.02509(15) 0.0281(6) Uani 1 1 d . . . H18 H -0.1590 0.8258 -0.0420 0.034 Uiso 1 1 calc R . . C19 C -0.0596(4) 0.92626(16) 0.02232(14) 0.0241(5) Uani 1 1 d . . . H19 H -0.1582 0.9529 0.0386 0.029 Uiso 1 1 calc R . . C20 C 0.5992(5) 0.9188(2) 0.3613(2) 0.0587(11) Uani 1 1 d . . . H20A H 0.6669 0.9315 0.4065 0.088 Uiso 1 1 calc R . . H20B H 0.6184 0.8567 0.3437 0.088 Uiso 1 1 calc R . . H20C H 0.4852 0.9258 0.3753 0.088 Uiso 1 1 calc R . . 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 0.0175(2) 0.0229(2) 0.0256(2) -0.00381(18) 0.0008(2) 0.0013(2) Cl1 0.0300(4) 0.0254(3) 0.0338(3) -0.0008(3) -0.0030(3) 0.0034(3) Cl2 0.0227(3) 0.0308(3) 0.0346(4) -0.0043(3) -0.0008(3) -0.0030(3) O1 0.0208(9) 0.0311(9) 0.0322(9) -0.0046(8) 0.0013(9) -0.0016(9) O2 0.0280(10) 0.0347(10) 0.0303(9) 0.0026(8) 0.0026(9) -0.0038(11) O3 0.0391(13) 0.0587(13) 0.0356(12) 0.0035(11) 0.0038(10) -0.0104(12) N1 0.0193(11) 0.0201(10) 0.0206(10) -0.0040(9) -0.0014(9) 0.0012(9) N2 0.0255(13) 0.0256(11) 0.0226(11) -0.0041(9) 0.0028(9) -0.0014(9) N3 0.0214(12) 0.0193(10) 0.0211(10) -0.0020(9) 0.0022(9) 0.0005(9) C1 0.0240(14) 0.0233(12) 0.0204(12) 0.0028(11) -0.0004(11) -0.0001(11) C2 0.0229(14) 0.0240(13) 0.0177(12) 0.0005(11) -0.0002(11) 0.0052(11) C3 0.0286(16) 0.0293(14) 0.0153(12) 0.0028(11) 0.0002(10) 0.0040(11) C4 0.0251(16) 0.0423(16) 0.0206(13) 0.0030(12) 0.0024(11) 0.0044(13) C5 0.0407(18) 0.0381(15) 0.0185(12) -0.0026(11) 0.0017(14) 0.0150(15) C6 0.045(2) 0.0278(14) 0.0229(14) -0.0044(11) -0.0007(12) 0.0056(13) C7 0.0286(16) 0.0311(15) 0.0212(13) 0.0019(12) 0.0010(12) 0.0001(13) C8 0.0278(15) 0.0224(13) 0.0237(13) -0.0007(11) 0.0012(11) 0.0051(11) C9 0.0255(15) 0.0253(13) 0.0215(13) -0.0006(11) 0.0027(12) 0.0018(12) C10 0.0359(16) 0.0303(13) 0.0253(12) -0.0019(11) 0.0087(13) -0.0023(14) C11 0.047(2) 0.0374(15) 0.0241(14) 0.0011(13) 0.0082(13) -0.0011(14) C12 0.0457(19) 0.0358(16) 0.0300(16) 0.0099(13) 0.0053(14) 0.0017(15) C13 0.0428(19) 0.0280(13) 0.0313(15) 0.0007(13) 0.0039(13) 0.0052(14) C14 0.0205(15) 0.0336(14) 0.0250(12) -0.0081(11) -0.0010(11) 0.0045(11) C15 0.0189(14) 0.0256(12) 0.0179(11) 0.0022(10) 0.0010(10) 0.0011(10) C16 0.0282(15) 0.0220(13) 0.0245(14) -0.0019(11) 0.0025(12) 0.0003(12) C17 0.0333(17) 0.0280(13) 0.0303(14) -0.0075(11) -0.0024(13) -0.0053(12) C18 0.0254(15) 0.0308(13) 0.0282(13) 0.0005(11) -0.0082(13) -0.0079(14) C19 0.0210(13) 0.0273(12) 0.0239(12) 0.0027(10) -0.0013(12) -0.0014(13) C20 0.087(3) 0.0492(19) 0.0397(18) 0.0067(17) 0.0073(19) -0.012(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag V1 O1 1.6003(18) . ? V1 N3 2.114(2) . ? V1 N2 2.131(2) . ? V1 Cl2 2.3400(8) . ? V1 Cl1 2.3540(7) . ? V1 N1 2.380(2) . ? O2 C3 1.370(3) . ? O2 H2O 0.8635 . ? O3 C20 1.402(4) . ? O3 H3O 0.9439 . ? N1 C8 1.485(3) . ? N1 C14 1.496(3) . ? N1 C1 1.497(3) . ? N2 C9 1.348(3) . ? N2 C10 1.349(3) . ? N3 C15 1.342(3) . ? N3 C16 1.348(3) . ? C1 C2 1.515(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.392(4) . ? C2 C7 1.393(4) . ? C3 C4 1.384(4) . ? C4 C5 1.374(4) . ? C4 H4 0.9500 . ? C5 C6 1.392(5) . ? C5 H5 0.9500 . ? C6 C7 1.386(4) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.497(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C13 1.382(4) . ? C10 C11 1.372(4) . ? C10 H10 0.9500 . ? C11 C12 1.384(4) . ? C11 H11 0.9500 . ? C12 C13 1.385(4) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.504(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C19 1.387(4) . ? C16 C17 1.374(4) . ? C16 H16 0.9500 . ? C17 C18 1.376(4) . ? C17 H17 0.9500 . ? C18 C19 1.380(3) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 V1 N3 93.87(9) . . ? O1 V1 N2 93.42(8) . . ? N3 V1 N2 84.93(8) . . ? O1 V1 Cl2 101.69(7) . . ? N3 V1 Cl2 163.71(6) . . ? N2 V1 Cl2 89.35(6) . . ? O1 V1 Cl1 101.39(7) . . ? N3 V1 Cl1 89.19(6) . . ? N2 V1 Cl1 164.41(6) . . ? Cl2 V1 Cl1 92.37(3) . . ? O1 V1 N1 163.63(9) . . ? N3 V1 N1 76.12(8) . . ? N2 V1 N1 73.07(8) . . ? Cl2 V1 N1 87.64(5) . . ? Cl1 V1 N1 91.51(5) . . ? C3 O2 H2O 114.5 . . ? C20 O3 H3O 112.5 . . ? C8 N1 C14 108.7(2) . . ? C8 N1 C1 110.67(19) . . ? C14 N1 C1 111.5(2) . . ? C8 N1 V1 103.95(15) . . ? C14 N1 V1 109.00(14) . . ? C1 N1 V1 112.70(15) . . ? C9 N2 C10 118.7(2) . . ? C9 N2 V1 120.10(16) . . ? C10 N2 V1 121.01(17) . . ? C15 N3 C16 118.3(2) . . ? C15 N3 V1 121.03(16) . . ? C16 N3 V1 120.63(18) . . ? N1 C1 C2 116.0(2) . . ? N1 C1 H1A 108.3 . . ? C2 C1 H1A 108.3 . . ? N1 C1 H1B 108.3 . . ? C2 C1 H1B 108.3 . . ? H1A C1 H1B 107.4 . . ? C3 C2 C7 118.3(2) . . ? C3 C2 C1 121.4(2) . . ? C7 C2 C1 120.3(2) . . ? O2 C3 C4 121.9(2) . . ? O2 C3 C2 117.6(2) . . ? C4 C3 C2 120.4(2) . . ? C5 C4 C3 120.3(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.6(3) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C7 C6 C5 118.5(3) . . ? C7 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? C6 C7 C2 121.7(3) . . ? C6 C7 H7 119.2 . . ? C2 C7 H7 119.2 . . ? N1 C8 C9 109.4(2) . . ? N1 C8 H8A 109.8 . . ? C9 C8 H8A 109.8 . . ? N1 C8 H8B 109.8 . . ? C9 C8 H8B 109.8 . . ? H8A C8 H8B 108.2 . . ? N2 C9 C13 121.7(2) . . ? N2 C9 C8 115.2(2) . . ? C13 C9 C8 123.2(2) . . ? N2 C10 C11 122.4(2) . . ? N2 C10 H10 118.8 . . ? C11 C10 H10 118.8 . . ? C10 C11 C12 118.9(3) . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? C11 C12 C13 119.2(3) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C9 C13 C12 119.1(3) . . ? C9 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? N1 C14 C15 114.2(2) . . ? N1 C14 H14A 108.7 . . ? C15 C14 H14A 108.7 . . ? N1 C14 H14B 108.7 . . ? C15 C14 H14B 108.7 . . ? H14A C14 H14B 107.6 . . ? N3 C15 C19 122.1(2) . . ? N3 C15 C14 118.7(2) . . ? C19 C15 C14 119.1(2) . . ? N3 C16 C17 122.6(3) . . ? N3 C16 H16 118.7 . . ? C17 C16 H16 118.7 . . ? C16 C17 C18 118.7(2) . . ? C16 C17 H17 120.6 . . ? C18 C17 H17 120.6 . . ? C17 C18 C19 119.6(3) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C18 C19 C15 118.7(3) . . ? C18 C19 H19 120.7 . . ? C15 C19 H19 120.7 . . ? O3 C20 H20A 109.5 . . ? O3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2O O3 0.86 1.82 2.685(3) 174.8 1_455 O3 H3O Cl1 0.94 2.35 3.220(2) 153.2 . O3 H3O Cl2 0.94 2.71 3.278(2) 119.0 . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.276 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.057