# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 858688' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H12 N O10 V' _chemical_formula_weight 417.20 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 7.1920(6) _cell_length_b 15.4368(12) _cell_length_c 14.2060(12) _cell_angle_alpha 90.00 _cell_angle_beta 91.894(5) _cell_angle_gamma 90.00 _cell_volume 1576.3(2) _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 ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.758 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.691 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11312 _diffrn_reflns_av_R_equivalents 0.0715 _diffrn_reflns_av_sigmaI/netI 0.0785 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 28.33 _reflns_number_total 3916 _reflns_number_gt 2512 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0488P)^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 _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3916 _refine_ls_number_parameters 292 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0766 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1033 _refine_ls_wR_factor_gt 0.0904 _refine_ls_goodness_of_fit_ref 0.937 _refine_ls_restrained_S_all 0.937 _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 0.16178(5) 0.44291(2) 0.15404(3) 0.02382(13) Uani 1 1 d . . . N N 0.3367(2) 0.54089(12) 0.21011(14) 0.0228(4) Uani 1 1 d . . . C1 C 0.0862(3) 0.63073(15) 0.16757(17) 0.0267(5) Uani 1 1 d . . . C2 C 0.2795(3) 0.62321(15) 0.21090(17) 0.0245(5) Uani 1 1 d . . . C3 C 0.3904(3) 0.68915(17) 0.24605(18) 0.0285(6) Uani 1 1 d . . . C4 C 0.5670(4) 0.66820(16) 0.28232(19) 0.0320(6) Uani 1 1 d . . . C5 C 0.6253(3) 0.58277(16) 0.28258(19) 0.0303(6) Uani 1 1 d . . . C6 C 0.5055(3) 0.52004(15) 0.24527(16) 0.0228(5) Uani 1 1 d . . . C7 C 0.5389(3) 0.42435(15) 0.23872(17) 0.0246(5) Uani 1 1 d . . . C8 C -0.0462(3) 0.32696(15) 0.08945(17) 0.0257(5) Uani 1 1 d . . . C9 C -0.1656(3) 0.25449(15) 0.05579(17) 0.0255(5) Uani 1 1 d . . . C10 C -0.0990(4) 0.17015(17) 0.0646(2) 0.0353(7) Uani 1 1 d . . . C11 C -0.2064(4) 0.10047(18) 0.0343(2) 0.0411(7) Uani 1 1 d . . . C12 C -0.3811(4) 0.11563(17) -0.0056(2) 0.0365(7) Uani 1 1 d . . . C13 C -0.4506(3) 0.19994(15) -0.01488(17) 0.0270(6) Uani 1 1 d . . . C14 C -0.6389(3) 0.21059(17) -0.06006(18) 0.0296(6) Uani 1 1 d . . . C15 C -0.3427(3) 0.26937(16) 0.01613(17) 0.0253(5) Uani 1 1 d . . . O1 O 0.2748(3) 0.46041(15) 0.02200(14) 0.0332(5) Uani 1 1 d . . . O2 O 0.0448(3) 0.42842(12) 0.28328(13) 0.0318(4) Uani 1 1 d . . . O3 O 0.0193(2) 0.55814(10) 0.13792(12) 0.0301(4) Uani 1 1 d . . . O4 O 0.0067(2) 0.70125(10) 0.16347(14) 0.0387(5) Uani 1 1 d . . . O5 O 0.4015(2) 0.38359(10) 0.19930(13) 0.0308(4) Uani 1 1 d . . . O6 O 0.6841(2) 0.39100(10) 0.26937(13) 0.0340(5) Uani 1 1 d . . . O7 O -0.0962(2) 0.40583(11) 0.08597(12) 0.0295(4) Uani 1 1 d . . . O8 O 0.1155(2) 0.31201(11) 0.12388(13) 0.0356(4) Uani 1 1 d . . . O9 O -0.6921(2) 0.29171(12) -0.07429(13) 0.0366(5) Uani 1 1 d . . . O10 O -0.7343(2) 0.14868(12) -0.08220(15) 0.0470(6) Uani 1 1 d . . . H3 H 0.353(3) 0.7457(16) 0.2437(16) 0.023(6) Uiso 1 1 d . . . H15 H -0.385(3) 0.3254(16) 0.0117(16) 0.027(7) Uiso 1 1 d . . . H4 H 0.643(4) 0.7149(17) 0.3051(18) 0.038(7) Uiso 1 1 d . . . H5 H 0.737(4) 0.5636(15) 0.3087(18) 0.027(7) Uiso 1 1 d . . . H10 H 0.015(4) 0.1611(16) 0.0878(18) 0.037(8) Uiso 1 1 d . . . H11 H -0.160(4) 0.0407(18) 0.0389(19) 0.045(8) Uiso 1 1 d . . . H12 H -0.456(4) 0.0684(17) -0.0277(19) 0.043(8) Uiso 1 1 d . . . H2B H 0.103(4) 0.3978(18) 0.324(2) 0.040(8) Uiso 1 1 d . . . H2A H -0.071(4) 0.418(2) 0.286(2) 0.059(10) Uiso 1 1 d . . . H1A H 0.228(6) 0.493(3) -0.006(3) 0.094(17) Uiso 1 1 d . . . H1B H 0.292(4) 0.417(2) -0.005(2) 0.059(12) Uiso 1 1 d . . . H9 H -0.806(5) 0.284(2) -0.102(3) 0.096(14) 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 0.0159(2) 0.0216(2) 0.0332(3) 0.00124(18) -0.01038(16) -0.00075(16) N 0.0159(9) 0.0235(10) 0.0288(11) 0.0029(8) -0.0047(8) 0.0000(7) C1 0.0225(12) 0.0273(13) 0.0299(14) 0.0022(10) -0.0056(10) 0.0044(10) C2 0.0210(12) 0.0257(12) 0.0267(14) 0.0016(10) -0.0022(10) 0.0016(10) C3 0.0277(13) 0.0232(13) 0.0345(15) 0.0020(11) -0.0029(11) -0.0005(10) C4 0.0308(14) 0.0256(13) 0.0392(16) -0.0043(12) -0.0059(12) -0.0066(11) C5 0.0209(12) 0.0310(14) 0.0382(16) -0.0008(11) -0.0087(11) -0.0020(10) C6 0.0163(11) 0.0243(12) 0.0275(13) 0.0024(10) -0.0038(10) -0.0012(9) C7 0.0165(11) 0.0261(13) 0.0309(14) 0.0004(10) -0.0038(10) -0.0017(9) C8 0.0211(12) 0.0289(13) 0.0268(13) 0.0030(10) -0.0048(10) -0.0051(10) C9 0.0222(12) 0.0272(13) 0.0267(13) -0.0011(10) -0.0051(10) -0.0044(10) C10 0.0240(13) 0.0342(15) 0.0469(18) -0.0019(13) -0.0103(13) 0.0011(11) C11 0.0380(16) 0.0261(14) 0.058(2) -0.0017(14) -0.0134(14) 0.0010(12) C12 0.0343(15) 0.0285(14) 0.0459(18) -0.0051(12) -0.0093(13) -0.0077(12) C13 0.0220(12) 0.0291(13) 0.0292(14) -0.0006(10) -0.0073(10) -0.0038(10) C14 0.0240(13) 0.0363(15) 0.0281(14) -0.0031(11) -0.0041(11) -0.0050(11) C15 0.0232(12) 0.0244(13) 0.0277(14) -0.0009(10) -0.0073(10) -0.0009(10) O1 0.0272(10) 0.0365(12) 0.0355(12) 0.0009(10) -0.0063(9) 0.0030(8) O2 0.0179(9) 0.0399(11) 0.0369(11) 0.0093(9) -0.0096(8) 0.0001(8) O3 0.0199(8) 0.0277(9) 0.0419(11) 0.0002(8) -0.0117(7) 0.0022(7) O4 0.0270(10) 0.0267(9) 0.0611(13) -0.0024(9) -0.0157(9) 0.0089(8) O5 0.0194(8) 0.0212(8) 0.0508(12) -0.0013(8) -0.0144(8) -0.0006(7) O6 0.0168(8) 0.0273(9) 0.0568(13) 0.0037(8) -0.0139(8) 0.0013(7) O7 0.0221(8) 0.0263(9) 0.0393(11) 0.0009(8) -0.0127(7) -0.0021(7) O8 0.0247(9) 0.0288(9) 0.0520(12) -0.0006(9) -0.0187(8) -0.0024(7) O9 0.0259(10) 0.0362(11) 0.0466(12) -0.0027(9) -0.0146(9) 0.0000(8) O10 0.0342(11) 0.0396(11) 0.0656(15) -0.0078(10) -0.0244(10) -0.0084(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 O5 2.0375(15) . ? V1 O2 2.057(2) . ? V1 O3 2.0617(16) . ? V1 O1 2.086(2) . ? V1 O8 2.0901(17) . ? V1 N 2.1066(18) . ? V1 O7 2.1420(15) . ? N C2 1.336(3) . ? N C6 1.337(3) . ? C1 O4 1.230(3) . ? C1 O3 1.285(3) . ? C1 C2 1.506(3) . ? C2 C3 1.377(3) . ? C3 C4 1.393(3) . ? C4 C5 1.384(3) . ? C5 C6 1.389(3) . ? C6 C7 1.500(3) . ? C7 O6 1.231(3) . ? C7 O5 1.284(3) . ? C8 O8 1.268(3) . ? C8 O7 1.270(3) . ? C8 C9 1.480(3) . ? C9 C10 1.392(3) . ? C9 C15 1.394(3) . ? C10 C11 1.385(4) . ? C11 C12 1.381(4) . ? C12 C13 1.399(4) . ? C13 C15 1.387(3) . ? C13 C14 1.488(3) . ? C14 O10 1.212(3) . ? C14 O9 1.323(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 O5 V1 O2 92.07(7) . . ? O5 V1 O3 146.62(6) . . ? O2 V1 O3 88.66(7) . . ? O5 V1 O1 89.49(8) . . ? O2 V1 O1 178.35(8) . . ? O3 V1 O1 89.74(8) . . ? O5 V1 O8 75.97(6) . . ? O2 V1 O8 90.61(8) . . ? O3 V1 O8 137.41(6) . . ? O1 V1 O8 90.29(9) . . ? O5 V1 N 73.43(6) . . ? O2 V1 N 89.85(8) . . ? O3 V1 N 73.20(7) . . ? O1 V1 N 90.08(8) . . ? O8 V1 N 149.39(7) . . ? O5 V1 O7 137.21(7) . . ? O2 V1 O7 90.01(7) . . ? O3 V1 O7 76.14(6) . . ? O1 V1 O7 89.21(7) . . ? O8 V1 O7 61.27(6) . . ? N V1 O7 149.34(7) . . ? C2 N C6 120.13(19) . . ? C2 N V1 120.39(14) . . ? C6 N V1 119.48(15) . . ? O4 C1 O3 126.0(2) . . ? O4 C1 C2 120.6(2) . . ? O3 C1 C2 113.39(19) . . ? N C2 C3 122.1(2) . . ? N C2 C1 110.50(19) . . ? C3 C2 C1 127.4(2) . . ? C2 C3 C4 118.2(2) . . ? C5 C4 C3 119.6(2) . . ? C4 C5 C6 118.7(2) . . ? N C6 C5 121.2(2) . . ? N C6 C7 111.05(18) . . ? C5 C6 C7 127.7(2) . . ? O6 C7 O5 125.5(2) . . ? O6 C7 C6 121.7(2) . . ? O5 C7 C6 112.77(19) . . ? O8 C8 O7 116.4(2) . . ? O8 C8 C9 120.1(2) . . ? O7 C8 C9 123.5(2) . . ? C10 C9 C15 119.9(2) . . ? C10 C9 C8 118.9(2) . . ? C15 C9 C8 121.2(2) . . ? C11 C10 C9 120.8(2) . . ? C12 C11 C10 119.1(3) . . ? C11 C12 C13 120.9(2) . . ? C15 C13 C12 119.6(2) . . ? C15 C13 C14 122.9(2) . . ? C12 C13 C14 117.4(2) . . ? O10 C14 O9 123.2(2) . . ? O10 C14 C13 121.6(2) . . ? O9 C14 C13 115.2(2) . . ? C13 C15 C9 119.7(2) . . ? C1 O3 V1 122.47(14) . . ? C7 O5 V1 123.25(14) . . ? C8 O7 V1 89.92(13) . . ? C8 O8 V1 92.35(14) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.453 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.075 data_2 _database_code_depnum_ccdc_archive 'CCDC 858689' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H22 N2 O22 V2' _chemical_formula_weight 792.32 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' V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1031(16) _cell_length_b 9.7398(19) _cell_length_c 10.142(2) _cell_angle_alpha 103.42(3) _cell_angle_beta 109.89(3) _cell_angle_gamma 90.08(3) _cell_volume 729.3(2) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.804 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 402 _exptl_absorpt_coefficient_mu 0.746 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _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 7242 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3320 _reflns_number_gt 2935 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0470P)^2^+0.2016P] 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 3320 _refine_ls_number_parameters 243 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0330 _refine_ls_R_factor_gt 0.0286 _refine_ls_wR_factor_ref 0.0821 _refine_ls_wR_factor_gt 0.0801 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 H1WA H 0.879(6) 0.931(5) 0.664(5) 0.106(15) Uiso 1 1 d . . . H1WB H 0.964(6) 1.013(4) 0.767(5) 0.100(15) Uiso 1 1 d . . . V1 V 0.87882(3) 0.30396(3) 0.09094(3) 0.01693(9) Uani 1 1 d . . . O1 O 1.03361(16) 0.27493(12) -0.03633(13) 0.0248(3) Uani 1 1 d . . . H1A H 1.1327 0.2184 0.0099 0.070(9) Uiso 1 1 d R . . H1B H 1.0756 0.3505 -0.0507 0.045(7) Uiso 1 1 d R . . O2 O 0.74173(17) 0.33164(16) 0.23003(14) 0.0356(3) Uani 1 1 d . . . H2A H 0.6475 0.3671 0.2095 0.047(7) Uiso 1 1 d R . . H2B H 0.7817 0.3163 0.3140 0.036(6) Uiso 1 1 d R . . O3 O 0.77898(15) 0.47302(12) 0.01287(12) 0.0225(2) Uani 1 1 d . . . O4 O 0.56486(17) 0.56537(13) -0.13613(14) 0.0303(3) Uani 1 1 d . . . O5 O 0.85622(16) 0.08833(12) 0.06007(14) 0.0276(3) Uani 1 1 d . . . O6 O 0.70115(19) -0.12071(13) -0.06176(17) 0.0385(3) Uani 1 1 d . . . O7 O 1.09364(15) 0.27286(12) 0.26828(13) 0.0266(3) Uani 1 1 d . . . O8 O 1.05784(16) 0.48139(12) 0.22824(13) 0.0288(3) Uani 1 1 d . . . O9 O 1.14215(19) 0.73070(16) 0.50268(15) 0.0380(3) Uani 1 1 d . . . O10 O 1.2786(2) 0.78873(16) 0.36364(17) 0.0413(4) Uani 1 1 d . . . H10 H 1.2147 0.8501 0.3564 0.059(8) Uiso 1 1 d R . . N1 N 0.63973(18) 0.22768(14) -0.08154(14) 0.0197(3) Uani 1 1 d . . . C1 C 0.6283(2) 0.46497(17) -0.08861(17) 0.0200(3) Uani 1 1 d . . . C2 C 0.5377(2) 0.31809(17) -0.14536(17) 0.0208(3) Uani 1 1 d . . . C3 C 0.3733(2) 0.2747(2) -0.25050(19) 0.0292(4) Uani 1 1 d . . . H3 H 0.2838 0.3459 -0.2959 0.048(7) Uiso 1 1 d R . . C4 C 0.3172(3) 0.1307(2) -0.2914(2) 0.0363(4) Uani 1 1 d . . . H4 H 0.1989 0.0982 -0.3703 0.047(7) Uiso 1 1 d R . . C5 C 0.4261(3) 0.0369(2) -0.2274(2) 0.0331(4) Uani 1 1 d . . . H5 H 0.3854 -0.0831 -0.2457 0.069(9) Uiso 1 1 d R . . C6 C 0.5871(2) 0.08960(17) -0.12119(18) 0.0240(3) Uani 1 1 d . . . C7 C 0.7238(2) 0.00870(17) -0.0363(2) 0.0252(3) Uani 1 1 d . . . C8 C 1.1508(2) 0.40176(17) 0.29925(17) 0.0220(3) Uani 1 1 d . . . C9 C 1.3280(2) 0.45468(17) 0.40890(16) 0.0206(3) Uani 1 1 d . . . C10 C 1.3776(2) 0.59956(17) 0.46679(16) 0.0206(3) Uani 1 1 d . . . C11 C 1.2494(2) 0.71097(18) 0.44335(17) 0.0231(3) Uani 1 1 d . . . C12 C 1.4500(2) 0.35633(17) 0.44247(17) 0.0227(3) Uani 1 1 d . . . H12 H 1.4058 0.2434 0.3885 0.044(6) Uiso 1 1 d R . . O1W O 0.9160(3) 1.0062(2) 0.6931(2) 0.0523(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 0.01362(14) 0.01621(14) 0.01931(14) 0.00726(10) 0.00179(10) 0.00162(9) O1 0.0234(6) 0.0230(6) 0.0300(6) 0.0083(5) 0.0108(5) 0.0013(5) O2 0.0255(7) 0.0628(9) 0.0285(7) 0.0254(7) 0.0127(5) 0.0209(6) O3 0.0182(6) 0.0201(5) 0.0257(6) 0.0107(5) 0.0001(5) 0.0018(4) O4 0.0263(7) 0.0283(6) 0.0374(7) 0.0191(6) 0.0053(5) 0.0091(5) O5 0.0220(6) 0.0199(6) 0.0378(7) 0.0113(5) 0.0037(5) 0.0017(5) O6 0.0325(7) 0.0171(6) 0.0611(9) 0.0089(6) 0.0109(7) 0.0012(5) O7 0.0197(6) 0.0239(6) 0.0303(6) 0.0114(5) -0.0016(5) -0.0003(5) O8 0.0243(6) 0.0221(6) 0.0278(6) 0.0067(5) -0.0064(5) 0.0024(5) O9 0.0387(8) 0.0512(8) 0.0376(7) 0.0253(7) 0.0208(6) 0.0252(7) O10 0.0434(8) 0.0448(8) 0.0566(9) 0.0360(7) 0.0284(7) 0.0244(7) N1 0.0178(6) 0.0196(6) 0.0201(6) 0.0049(5) 0.0047(5) 0.0011(5) C1 0.0171(7) 0.0239(7) 0.0212(7) 0.0092(6) 0.0069(6) 0.0034(6) C2 0.0178(8) 0.0250(8) 0.0197(7) 0.0075(6) 0.0055(6) 0.0025(6) C3 0.0200(8) 0.0364(9) 0.0264(8) 0.0097(7) 0.0008(7) 0.0029(7) C4 0.0230(9) 0.0432(11) 0.0309(10) 0.0043(8) -0.0019(7) -0.0065(8) C5 0.0268(9) 0.0296(9) 0.0355(10) 0.0008(8) 0.0063(8) -0.0068(7) C6 0.0220(8) 0.0217(8) 0.0273(8) 0.0041(7) 0.0087(7) -0.0005(6) C7 0.0212(8) 0.0201(7) 0.0356(9) 0.0070(7) 0.0113(7) 0.0013(6) C8 0.0185(8) 0.0253(8) 0.0190(7) 0.0053(6) 0.0028(6) 0.0044(6) C9 0.0181(7) 0.0250(8) 0.0167(7) 0.0066(6) 0.0024(6) 0.0036(6) C10 0.0196(8) 0.0243(8) 0.0166(7) 0.0067(6) 0.0034(6) 0.0054(6) C11 0.0228(8) 0.0246(8) 0.0176(7) 0.0054(6) 0.0017(6) 0.0059(6) C12 0.0210(8) 0.0226(7) 0.0201(7) 0.0057(6) 0.0016(6) 0.0029(6) O1W 0.0557(11) 0.0335(8) 0.0545(11) 0.0226(8) -0.0051(9) 0.0070(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 O3 2.0410(12) . ? V1 O2 2.0463(14) . ? V1 O5 2.0487(12) . ? V1 O1 2.0621(13) . ? V1 N1 2.1100(17) . ? V1 O7 2.1167(14) . ? V1 O8 2.1287(16) . ? O3 C1 1.290(2) . ? O4 C1 1.227(2) . ? O5 C7 1.281(2) . ? O6 C7 1.227(2) . ? O7 C8 1.267(2) . ? O8 C8 1.257(2) . ? O9 C11 1.207(2) . ? O10 C11 1.303(2) . ? N1 C2 1.334(2) . ? N1 C6 1.335(2) . ? C1 C2 1.498(2) . ? C2 C3 1.383(2) . ? C3 C4 1.394(3) . ? C4 C5 1.387(3) . ? C5 C6 1.382(3) . ? C6 C7 1.503(2) . ? C8 C9 1.487(2) . ? C9 C12 1.391(2) . ? C9 C10 1.397(2) . ? C10 C12 1.387(2) 2_866 ? C10 C11 1.506(2) . ? C12 C10 1.387(2) 2_866 ? 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 O3 V1 O2 92.36(6) . . ? O3 V1 O5 145.98(5) . . ? O2 V1 O5 91.79(6) . . ? O3 V1 O1 90.51(5) . . ? O2 V1 O1 175.69(5) . . ? O5 V1 O1 87.62(6) . . ? O3 V1 N1 72.97(6) . . ? O2 V1 N1 88.60(6) . . ? O5 V1 N1 73.40(6) . . ? O1 V1 N1 95.32(5) . . ? O3 V1 O7 136.13(5) . . ? O2 V1 O7 85.34(5) . . ? O5 V1 O7 77.87(6) . . ? O1 V1 O7 90.36(5) . . ? N1 V1 O7 150.42(5) . . ? O3 V1 O8 74.96(5) . . ? O2 V1 O8 90.03(6) . . ? O5 V1 O8 138.79(5) . . ? O1 V1 O8 87.61(6) . . ? N1 V1 O8 147.81(5) . . ? O7 V1 O8 61.26(5) . . ? C1 O3 V1 123.24(11) . . ? C7 O5 V1 122.77(11) . . ? C8 O7 V1 90.36(10) . . ? C8 O8 V1 90.10(10) . . ? C2 N1 C6 120.32(14) . . ? C2 N1 V1 120.01(11) . . ? C6 N1 V1 119.58(11) . . ? O4 C1 O3 124.38(16) . . ? O4 C1 C2 122.77(15) . . ? O3 C1 C2 112.84(14) . . ? N1 C2 C3 122.12(15) . . ? N1 C2 C1 110.57(14) . . ? C3 C2 C1 127.31(15) . . ? C2 C3 C4 117.74(17) . . ? C5 C4 C3 119.75(17) . . ? C6 C5 C4 118.76(17) . . ? N1 C6 C5 121.28(16) . . ? N1 C6 C7 110.85(15) . . ? C5 C6 C7 127.87(16) . . ? O6 C7 O5 126.61(17) . . ? O6 C7 C6 120.12(16) . . ? O5 C7 C6 113.27(14) . . ? O8 C8 O7 117.96(15) . . ? O8 C8 C9 120.96(15) . . ? O7 C8 C9 120.94(14) . . ? C12 C9 C10 120.34(15) . . ? C12 C9 C8 118.02(15) . . ? C10 C9 C8 121.36(14) . . ? C12 C10 C9 119.02(15) 2_866 . ? C12 C10 C11 117.83(15) 2_866 . ? C9 C10 C11 123.03(15) . . ? O9 C11 O10 125.05(16) . . ? O9 C11 C10 122.29(15) . . ? O10 C11 C10 112.41(15) . . ? C10 C12 C9 120.64(15) 2_866 . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.376 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.059