Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Michal Sivak' 'Jaromir Marek' 'Peter Schwendt' 'Jozef Tatiersky' _publ_contact_author_name 'ProfD Michal Sivak' _publ_contact_author_address ; Department of Inorganic Chemistry Comenius University, Faculty of Natural Sciences Mlynska dolina Bratislava 84215 SLOVAKIA ; _publ_contact_author_email SIVAK@FNS.UNIBA.SK _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Racemic monoperoxovanadium(V) complexes with achiral OO and ON donor set heteroligands: synthesis, crystal structure and stereochemistry of [NH3(CH2)2NH3] [VO(O2)(ox)(pic)] . 2H2O and [NH3(CH2)2NH3][VO(O2)(ox)(pca)] ; data_fp2 _database_code_depnum_ccdc_archive 'CCDC 267202' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H4 N O9 V, C2 H10 N2, 2(H2 O) ' _chemical_formula_sum 'C10 H18 N3 O11 V' _chemical_formula_weight 407.21 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 'P 21/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 10.3089(8) _cell_length_b 10.1907(7) _cell_length_c 15.7381(11) _cell_angle_alpha 90.00 _cell_angle_beta 106.367(8) _cell_angle_gamma 90.00 _cell_volume 1586.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3619 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.705 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.692 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'Enhance (Oxford Diffraction)' _diffrn_measurement_device_type 'Kuma KM4 + CCD' _diffrn_measurement_method 'rotation method, \w--scan' _diffrn_detector_area_resol_mean 16.3 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9362 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2783 _reflns_number_gt 2547 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction)' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Johnson & Burnett, 1996)' _computing_publication_material ; SHELXL-97, PARST (Nardelli, 1995) ; _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^)+(0.0450P)^2^+0.7500P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2783 _refine_ls_number_parameters 244 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0325 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0751 _refine_ls_wR_factor_gt 0.0723 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.013 _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 0.18769(3) 0.13936(3) 0.261944(19) 0.01093(11) Uani 1 1 d . . . O1 O 0.09204(13) 0.25947(12) 0.26944(8) 0.0162(3) Uani 1 1 d . . . O2 O 0.23794(12) 0.19640(12) 0.15851(8) 0.0152(3) Uani 1 1 d . . . O3 O 0.33613(12) 0.22589(12) 0.24137(8) 0.0148(3) Uani 1 1 d . . . O4 O 0.10265(12) 0.01558(12) 0.33497(8) 0.0147(3) Uani 1 1 d . . . O5 O 0.32379(12) 0.14305(12) 0.38391(8) 0.0155(3) Uani 1 1 d . . . O6 O 0.12317(13) -0.06423(13) 0.47022(8) 0.0171(3) Uani 1 1 d . . . O7 O 0.35936(13) 0.08761(14) 0.52623(8) 0.0217(3) Uani 1 1 d . . . O8 O 0.27008(12) -0.04496(12) 0.23354(8) 0.0142(3) Uani 1 1 d . . . O9 O 0.23499(14) -0.21565(13) 0.14037(9) 0.0211(3) Uani 1 1 d . . . N1 N 0.03101(14) 0.05400(15) 0.15906(9) 0.0126(3) Uani 1 1 d . . . C1 C 0.16381(18) 0.00202(17) 0.41794(12) 0.0132(4) Uani 1 1 d . . . C2 C 0.29497(18) 0.08277(17) 0.44840(11) 0.0139(4) Uani 1 1 d . . . C3 C 0.19794(18) -0.11489(18) 0.16992(11) 0.0134(4) Uani 1 1 d . . . C4 C 0.05694(18) -0.06380(18) 0.12914(11) 0.0133(4) Uani 1 1 d . . . C5 C -0.0389(2) -0.13169(19) 0.06521(12) 0.0176(4) Uani 1 1 d . . . H5 H -0.0181 -0.2143 0.0444 0.021 Uiso 1 1 calc R . . C6 C -0.1661(2) -0.0769(2) 0.03209(12) 0.0222(5) Uani 1 1 d . . . H6 H -0.2350 -0.1232 -0.0101 0.027 Uiso 1 1 calc R . . C7 C -0.19189(19) 0.0457(2) 0.06098(12) 0.0212(4) Uani 1 1 d . . . H7 H -0.2778 0.0858 0.0379 0.025 Uiso 1 1 calc R . . C8 C -0.09009(18) 0.1093(2) 0.12434(12) 0.0164(4) Uani 1 1 d . . . H8 H -0.1068 0.1944 0.1436 0.020 Uiso 1 1 calc R . . O1W O 0.60485(14) 0.20996(13) 0.62436(9) 0.0204(3) Uani 1 1 d D . . O2W O 0.53053(14) 0.16709(14) 0.91809(9) 0.0220(3) Uani 1 1 d D . . N1A N 0.48742(16) -0.05953(16) 0.81743(10) 0.0172(3) Uani 1 1 d . . . H1A1 H 0.4904 0.0093 0.8548 0.026 Uiso 1 1 calc R . . H1A2 H 0.5726 -0.0785 0.8151 0.026 Uiso 1 1 calc R . . H1A3 H 0.4518 -0.1308 0.8376 0.026 Uiso 1 1 calc R . . C2A C 0.40156(18) -0.02456(18) 0.72730(12) 0.0152(4) Uani 1 1 d . . . H2A1 H 0.4110 -0.0918 0.6840 0.018 Uiso 1 1 calc R . . H2A2 H 0.4302 0.0611 0.7090 0.018 Uiso 1 1 calc R . . C3A C 0.25617(18) -0.01707(18) 0.72970(12) 0.0140(4) Uani 1 1 d . . . H3A1 H 0.2247 -0.1057 0.7405 0.017 Uiso 1 1 calc R . . H3A2 H 0.2499 0.0406 0.7790 0.017 Uiso 1 1 calc R . . N4A N 0.16828(15) 0.03492(15) 0.64519(10) 0.0153(3) Uani 1 1 d . . . H4A1 H 0.1915 0.1195 0.6381 0.023 Uiso 1 1 calc R . . H4A2 H 0.0804 0.0317 0.6461 0.023 Uiso 1 1 calc R . . H4A3 H 0.1789 -0.0145 0.5994 0.023 Uiso 1 1 calc R . . H1V H 0.5385(19) 0.167(2) 0.5853(13) 0.040(7) Uiso 1 1 d D . . H1W H 0.633(3) 0.151(2) 0.6677(13) 0.051(8) Uiso 1 1 d D . . H2V H 0.470(2) 0.230(2) 0.9119(18) 0.050(8) Uiso 1 1 d D . . H2W H 0.602(2) 0.203(3) 0.9049(19) 0.057(9) Uiso 1 1 d 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 0.00913(17) 0.01219(18) 0.01153(17) -0.00031(11) 0.00301(12) -0.00004(11) O1 0.0153(7) 0.0174(7) 0.0172(6) -0.0014(5) 0.0069(5) 0.0017(5) O2 0.0148(7) 0.0175(7) 0.0137(6) 0.0001(5) 0.0045(5) -0.0011(5) O3 0.0121(6) 0.0167(7) 0.0151(6) -0.0008(5) 0.0031(5) -0.0021(5) O4 0.0104(6) 0.0205(7) 0.0118(6) -0.0004(5) 0.0010(5) -0.0040(5) O5 0.0118(6) 0.0193(7) 0.0139(6) 0.0002(5) 0.0012(5) -0.0047(5) O6 0.0164(7) 0.0200(7) 0.0150(6) 0.0009(5) 0.0044(5) -0.0046(5) O7 0.0176(7) 0.0315(8) 0.0136(7) -0.0014(6) 0.0005(6) -0.0076(6) O8 0.0120(6) 0.0139(6) 0.0155(6) 0.0004(5) 0.0022(5) 0.0011(5) O9 0.0244(7) 0.0145(7) 0.0243(7) -0.0025(6) 0.0068(6) 0.0032(6) N1 0.0105(7) 0.0174(8) 0.0107(7) 0.0032(6) 0.0041(6) -0.0001(6) C1 0.0107(9) 0.0145(9) 0.0150(9) -0.0021(7) 0.0047(7) 0.0011(7) C2 0.0115(9) 0.0156(9) 0.0144(9) -0.0021(7) 0.0032(7) 0.0005(7) C3 0.0148(9) 0.0129(9) 0.0133(9) 0.0032(7) 0.0053(7) -0.0018(7) C4 0.0143(9) 0.0162(9) 0.0107(8) 0.0036(7) 0.0054(7) -0.0018(7) C5 0.0214(10) 0.0207(10) 0.0114(9) 0.0000(7) 0.0056(8) -0.0079(8) C6 0.0166(10) 0.0377(12) 0.0105(9) 0.0009(8) 0.0009(7) -0.0102(9) C7 0.0110(9) 0.0394(12) 0.0133(9) 0.0071(8) 0.0038(7) 0.0020(9) C8 0.0130(9) 0.0242(10) 0.0135(9) 0.0055(7) 0.0059(7) 0.0029(8) O1W 0.0201(7) 0.0196(7) 0.0179(7) 0.0014(6) -0.0005(6) -0.0020(6) O2W 0.0180(7) 0.0203(7) 0.0252(7) 0.0003(6) 0.0016(6) 0.0064(6) N1A 0.0125(8) 0.0186(8) 0.0211(8) -0.0011(7) 0.0059(6) 0.0025(6) C2A 0.0136(9) 0.0162(9) 0.0168(9) -0.0012(7) 0.0059(7) 0.0006(7) C3A 0.0138(9) 0.0138(9) 0.0159(9) -0.0006(7) 0.0067(7) -0.0011(7) N4A 0.0116(8) 0.0176(8) 0.0164(8) -0.0038(6) 0.0034(6) -0.0036(6) _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 1.5969(13) . ? V1 O3 1.8716(13) . ? V1 O2 1.9316(12) . ? V1 O5 2.0339(13) . ? V1 O4 2.0612(13) . ? V1 N1 2.1245(15) . ? V1 O8 2.1595(13) . ? O2 O3 1.4393(16) . ? O4 C1 1.288(2) . ? O5 C2 1.291(2) . ? O6 C1 1.226(2) . ? O7 C2 1.219(2) . ? O8 C3 1.282(2) . ? O9 C3 1.231(2) . ? N1 C8 1.338(2) . ? N1 C4 1.344(2) . ? C1 C2 1.539(2) . ? C3 C4 1.507(3) . ? C4 C5 1.381(3) . ? C5 C6 1.384(3) . ? C5 H5 0.9500 . ? C6 C7 1.381(3) . ? C6 H6 0.9500 . ? C7 C8 1.388(3) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? O1W H1V 0.892(10) . ? O1W H1W 0.894(10) . ? O2W H2V 0.887(10) . ? O2W H2W 0.894(10) . ? N1A C2A 1.488(2) . ? N1A H1A1 0.9100 . ? N1A H1A2 0.9100 . ? N1A H1A3 0.9100 . ? C2A C3A 1.512(2) . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? C3A N4A 1.480(2) . ? C3A H3A1 0.9900 . ? C3A H3A2 0.9900 . ? N4A H4A1 0.9100 . ? N4A H4A2 0.9100 . ? N4A H4A3 0.9100 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 V1 O3 101.75(6) . . ? O1 V1 O2 98.59(6) . . ? O3 V1 O2 44.44(5) . . ? O1 V1 O5 101.08(6) . . ? O3 V1 O5 76.96(5) . . ? O2 V1 O5 120.81(5) . . ? O1 V1 O4 93.40(6) . . ? O3 V1 O4 151.85(5) . . ? O2 V1 O4 155.68(5) . . ? O5 V1 O4 76.93(5) . . ? O1 V1 N1 91.00(6) . . ? O3 V1 N1 122.97(5) . . ? O2 V1 N1 78.92(5) . . ? O5 V1 N1 154.29(5) . . ? O4 V1 N1 79.80(5) . . ? O1 V1 O8 165.71(6) . . ? O3 V1 O8 89.18(5) . . ? O2 V1 O8 82.70(5) . . ? O5 V1 O8 90.26(5) . . ? O4 V1 O8 80.62(5) . . ? N1 V1 O8 75.23(5) . . ? O3 O2 V1 65.57(7) . . ? O2 O3 V1 69.99(7) . . ? C1 O4 V1 117.87(11) . . ? C2 O5 V1 118.88(11) . . ? C3 O8 V1 118.02(11) . . ? C8 N1 C4 119.22(16) . . ? C8 N1 V1 124.07(13) . . ? C4 N1 V1 116.70(11) . . ? O6 C1 O4 125.28(16) . . ? O6 C1 C2 121.45(16) . . ? O4 C1 C2 113.24(15) . . ? O7 C2 O5 126.17(17) . . ? O7 C2 C1 121.10(16) . . ? O5 C2 C1 112.71(14) . . ? O9 C3 O8 125.80(17) . . ? O9 C3 C4 119.47(16) . . ? O8 C3 C4 114.72(15) . . ? N1 C4 C5 122.05(17) . . ? N1 C4 C3 115.01(15) . . ? C5 C4 C3 122.93(17) . . ? C4 C5 C6 118.67(18) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C7 C6 C5 119.38(17) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C6 C7 C8 118.86(18) . . ? C6 C7 H7 120.6 . . ? C8 C7 H7 120.6 . . ? N1 C8 C7 121.74(18) . . ? N1 C8 H8 119.1 . . ? C7 C8 H8 119.1 . . ? H1V O1W H1W 103(2) . . ? H2V O2W H2W 106(3) . . ? C2A N1A H1A1 109.5 . . ? C2A N1A H1A2 109.5 . . ? H1A1 N1A H1A2 109.5 . . ? C2A N1A H1A3 109.5 . . ? H1A1 N1A H1A3 109.5 . . ? H1A2 N1A H1A3 109.5 . . ? N1A C2A C3A 108.41(14) . . ? N1A C2A H2A1 110.0 . . ? C3A C2A H2A1 110.0 . . ? N1A C2A H2A2 110.0 . . ? C3A C2A H2A2 110.0 . . ? H2A1 C2A H2A2 108.4 . . ? N4A C3A C2A 110.84(14) . . ? N4A C3A H3A1 109.5 . . ? C2A C3A H3A1 109.5 . . ? N4A C3A H3A2 109.5 . . ? C2A C3A H3A2 109.5 . . ? H3A1 C3A H3A2 108.1 . . ? C3A N4A H4A1 109.5 . . ? C3A N4A H4A2 109.5 . . ? H4A1 N4A H4A2 109.5 . . ? C3A N4A H4A3 109.5 . . ? H4A1 N4A H4A3 109.5 . . ? H4A2 N4A H4A3 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.494 _refine_diff_density_min -0.408 _refine_diff_density_rms 0.056 data_fp3 _database_code_depnum_ccdc_archive 'CCDC 267203' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H3 N2 O9 V, C2 H10 N2 ' _chemical_formula_sum 'C9 H13 N4 O9 V' _chemical_formula_weight 372.17 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 'P 21/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 10.635(2) _cell_length_b 9.938(2) _cell_length_c 12.829(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.12(3) _cell_angle_gamma 90.00 _cell_volume 1342.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2445 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.842 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.799 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'Enhance (Oxford Diffraction)' _diffrn_measurement_device_type 'Kuma KM4 + CCD' _diffrn_measurement_method 'rotation method, \w--scan' _diffrn_detector_area_resol_mean 16.3 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7935 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.81 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2347 _reflns_number_gt 2094 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction)' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Johnson & Burnett, 1996)' _computing_publication_material ; SHELXL-97, PARST (Nardelli, 1995) ; _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^)+(0.0315P)^2^+1.5000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0034(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2347 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0731 _refine_ls_wR_factor_gt 0.0696 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.003 _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 0.07815(3) 0.21071(4) 0.25402(3) 0.01179(14) Uani 1 1 d . . . O1 O 0.16784(15) 0.34122(16) 0.27061(13) 0.0190(4) Uani 1 1 d . . . O2 O -0.08491(15) 0.28353(16) 0.22822(13) 0.0210(4) Uani 1 1 d . . . O3 O -0.03274(15) 0.27134(16) 0.13189(13) 0.0198(4) Uani 1 1 d . . . O4 O 0.01803(15) 0.19676(17) 0.39463(13) 0.0208(4) Uani 1 1 d . . . O5 O 0.21868(14) 0.09222(15) 0.33946(12) 0.0136(3) Uani 1 1 d . . . O6 O -0.00220(14) 0.01453(15) 0.21887(12) 0.0133(3) Uani 1 1 d . . . O8 O 0.28497(15) 0.01077(16) 0.50050(12) 0.0178(4) Uani 1 1 d . . . O7 O 0.07232(17) 0.13842(18) 0.56337(13) 0.0265(4) Uani 1 1 d . . . O9 O -0.00376(15) -0.16776(15) 0.11504(13) 0.0184(4) Uani 1 1 d . . . N1 N 0.17340(16) 0.13376(18) 0.13071(14) 0.0113(4) Uani 1 1 d . . . N2 N 0.24431(17) -0.00824(19) 0.71614(15) 0.0161(4) Uani 1 1 d . . . H2A H 0.2814 0.0647 0.7506 0.024 Uiso 1 1 calc R . . H2B H 0.1666 -0.0223 0.7362 0.024 Uiso 1 1 calc R . . H2C H 0.2352 0.0066 0.6455 0.024 Uiso 1 1 calc R . . N3 N 0.51333(17) -0.05770(19) 0.65698(15) 0.0146(4) Uani 1 1 d . . . H3A H 0.4895 -0.1205 0.6064 0.022 Uiso 1 1 calc R . . H3B H 0.5996 -0.0517 0.6685 0.022 Uiso 1 1 calc R . . H3C H 0.4798 0.0236 0.6353 0.022 Uiso 1 1 calc R . . C1 C 0.0906(2) 0.1405(2) 0.47170(18) 0.0174(5) Uani 1 1 d . . . C2 C 0.2091(2) 0.0741(2) 0.43705(17) 0.0136(5) Uani 1 1 d . . . C3 C 0.0366(2) -0.0567(2) 0.14658(17) 0.0118(5) Uani 1 1 d . . . C4 C 0.1396(2) 0.0102(2) 0.09526(17) 0.0117(5) Uani 1 1 d . . . C5 C 0.1951(2) -0.0480(2) 0.01460(18) 0.0161(5) Uani 1 1 d . . . H5 H 0.1696 -0.1359 -0.0086 0.019 Uiso 1 1 calc R . . N4 N 0.28351(19) 0.0160(2) -0.03171(16) 0.0215(5) Uani 1 1 d . . . C7 C 0.3153(2) 0.1398(3) 0.00498(18) 0.0212(5) Uani 1 1 d . . . H7 H 0.3776 0.1887 -0.0257 0.025 Uiso 1 1 calc R . . C8 C 0.2611(2) 0.1994(2) 0.08551(18) 0.0167(5) Uani 1 1 d . . . H8 H 0.2865 0.2873 0.1087 0.020 Uiso 1 1 calc R . . C9 C 0.3257(2) -0.1290(2) 0.74255(18) 0.0158(5) Uani 1 1 d . . . H9A H 0.3066 -0.1963 0.6856 0.019 Uiso 1 1 calc R . . H9B H 0.3041 -0.1695 0.8082 0.019 Uiso 1 1 calc R . . C10 C 0.4658(2) -0.0980(2) 0.75680(18) 0.0157(5) Uani 1 1 d . . . H10A H 0.4835 -0.0243 0.8088 0.019 Uiso 1 1 calc R . . H10B H 0.5132 -0.1784 0.7860 0.019 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 0.0114(2) 0.0099(2) 0.0141(2) 0.00018(15) 0.00150(14) 0.00115(15) O1 0.0191(9) 0.0138(8) 0.0220(9) -0.0006(7) -0.0041(7) -0.0022(7) O2 0.0162(8) 0.0187(9) 0.0275(10) -0.0006(7) 0.0013(7) 0.0033(7) O3 0.0183(9) 0.0180(9) 0.0216(9) 0.0004(7) -0.0028(7) 0.0011(7) O4 0.0201(9) 0.0247(9) 0.0190(9) 0.0030(7) 0.0071(7) 0.0095(7) O5 0.0129(8) 0.0152(8) 0.0131(8) 0.0008(6) 0.0032(6) 0.0031(6) O6 0.0130(8) 0.0127(8) 0.0151(8) 0.0006(6) 0.0049(6) -0.0008(6) O8 0.0196(9) 0.0190(9) 0.0144(8) 0.0020(7) 0.0004(7) 0.0042(7) O7 0.0322(10) 0.0315(10) 0.0178(9) 0.0024(8) 0.0110(8) 0.0111(8) O9 0.0225(9) 0.0106(8) 0.0222(9) 0.0011(7) 0.0028(7) -0.0041(7) N1 0.0119(9) 0.0115(9) 0.0098(9) 0.0035(7) -0.0007(7) -0.0002(7) N2 0.0139(10) 0.0186(10) 0.0162(10) -0.0004(8) 0.0038(8) -0.0020(8) N3 0.0110(9) 0.0131(9) 0.0200(11) -0.0010(8) 0.0028(8) 0.0009(7) C1 0.0207(13) 0.0143(12) 0.0179(13) -0.0005(10) 0.0058(10) 0.0026(10) C2 0.0171(12) 0.0097(11) 0.0143(12) -0.0019(9) 0.0028(9) -0.0031(9) C3 0.0114(11) 0.0107(11) 0.0125(11) 0.0047(9) -0.0007(9) 0.0017(9) C4 0.0110(11) 0.0125(11) 0.0109(11) 0.0034(9) -0.0015(9) 0.0024(9) C5 0.0162(12) 0.0180(12) 0.0138(12) 0.0004(9) 0.0013(9) 0.0000(9) N4 0.0184(11) 0.0316(12) 0.0151(10) -0.0011(9) 0.0042(8) -0.0022(9) C7 0.0173(12) 0.0295(14) 0.0169(12) 0.0056(11) 0.0032(10) -0.0054(11) C8 0.0150(11) 0.0161(12) 0.0182(12) 0.0061(10) -0.0002(9) -0.0027(9) C9 0.0184(12) 0.0137(11) 0.0163(12) 0.0007(9) 0.0052(9) -0.0017(9) C10 0.0180(12) 0.0143(11) 0.0146(12) 0.0007(9) 0.0020(9) 0.0011(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 1.6063(16) . ? V1 O2 1.8650(16) . ? V1 O3 1.9201(17) . ? V1 O4 2.0019(17) . ? V1 O5 2.0878(16) . ? V1 N1 2.1370(19) . ? V1 O6 2.1507(16) . ? O2 O3 1.430(2) . ? O4 C1 1.292(3) . ? O5 C2 1.283(3) . ? O6 C3 1.280(3) . ? O8 C2 1.235(3) . ? O7 C1 1.219(3) . ? O9 C3 1.232(3) . ? N1 C8 1.336(3) . ? N1 C4 1.340(3) . ? N2 C9 1.490(3) . ? N2 H2A 0.9100 . ? N2 H2B 0.9100 . ? N2 H2C 0.9100 . ? N3 C10 1.496(3) . ? N3 H3A 0.9100 . ? N3 H3B 0.9100 . ? N3 H3C 0.9100 . ? C1 C2 1.543(3) . ? C3 C4 1.511(3) . ? C4 C5 1.388(3) . ? C5 N4 1.341(3) . ? C5 H5 0.9500 . ? N4 C7 1.344(3) . ? C7 C8 1.385(3) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.507(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? 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 103.30(8) . . ? O1 V1 O3 98.02(8) . . ? O2 V1 O3 44.35(7) . . ? O1 V1 O4 101.29(8) . . ? O2 V1 O4 77.26(7) . . ? O3 V1 O4 121.30(7) . . ? O1 V1 O5 91.04(7) . . ? O2 V1 O5 152.97(7) . . ? O3 V1 O5 156.49(7) . . ? O4 V1 O5 77.52(6) . . ? O1 V1 N1 92.99(8) . . ? O2 V1 N1 122.25(7) . . ? O3 V1 N1 78.98(7) . . ? O4 V1 N1 152.55(7) . . ? O5 V1 N1 78.92(6) . . ? O1 V1 O6 166.09(7) . . ? O2 V1 O6 89.00(7) . . ? O3 V1 O6 86.18(7) . . ? O4 V1 O6 87.61(6) . . ? O5 V1 O6 80.36(6) . . ? N1 V1 O6 74.71(6) . . ? O3 O2 V1 69.87(9) . . ? O2 O3 V1 65.78(9) . . ? C1 O4 V1 119.15(14) . . ? C2 O5 V1 116.22(14) . . ? C3 O6 V1 119.61(13) . . ? C8 N1 C4 118.02(19) . . ? C8 N1 V1 125.44(15) . . ? C4 N1 V1 116.53(14) . . ? C9 N2 H2A 109.5 . . ? C9 N2 H2B 109.5 . . ? H2A N2 H2B 109.5 . . ? C9 N2 H2C 109.5 . . ? H2A N2 H2C 109.5 . . ? H2B N2 H2C 109.5 . . ? C10 N3 H3A 109.5 . . ? C10 N3 H3B 109.5 . . ? H3A N3 H3B 109.5 . . ? C10 N3 H3C 109.5 . . ? H3A N3 H3C 109.5 . . ? H3B N3 H3C 109.5 . . ? O7 C1 O4 125.9(2) . . ? O7 C1 C2 121.3(2) . . ? O4 C1 C2 112.86(19) . . ? O8 C2 O5 125.5(2) . . ? O8 C2 C1 120.8(2) . . ? O5 C2 C1 113.69(19) . . ? O9 C3 O6 126.9(2) . . ? O9 C3 C4 119.5(2) . . ? O6 C3 C4 113.57(18) . . ? N1 C4 C5 120.9(2) . . ? N1 C4 C3 115.57(19) . . ? C5 C4 C3 123.5(2) . . ? N4 C5 C4 122.1(2) . . ? N4 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? C5 N4 C7 115.9(2) . . ? N4 C7 C8 122.8(2) . . ? N4 C7 H7 118.6 . . ? C8 C7 H7 118.6 . . ? N1 C8 C7 120.3(2) . . ? N1 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? N2 C9 C10 113.29(18) . . ? N2 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? N2 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? N3 C10 C9 113.50(18) . . ? N3 C10 H10A 108.9 . . ? C9 C10 H10A 108.9 . . ? N3 C10 H10B 108.9 . . ? C9 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.485 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.056