Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 186 _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name 'Maurya, Mannar R.' 'Khurana, Shilpa' 'Rehder, Dieter' 'Zhang, Wenjian' _publ_contact_author_name 'Dr Mannar R Maurya' _publ_contact_author_address ; Department of Chemistry Indian Institute of Technology Roorkee 247 667 INDIA ; _publ_contact_author_email 'RKMANFCY@IITR.ERNET.IN' _publ_section_title ; Biomimetic oxo-, dioxo- and oxo-peroxo-hydrazonatovanadium(IV/V) complexes ; data_2vbhz _database_code_CSD 182866 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 N3 O3 V' _chemical_formula_weight 321.21 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 C2/c 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' '-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 16.2827(15) _cell_length_b 12.6396(12) _cell_length_c 14.7731(14) _cell_angle_alpha 90.00 _cell_angle_beta 119.7930(10) _cell_angle_gamma 90.00 _cell_volume 2638.5(4) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 4511 _cell_measurement_theta_min 2.161 _cell_measurement_theta_max 27.050 _exptl_crystal_description nadel _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.617 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.766 _exptl_absorpt_correction_type Multi_scan _exptl_absorpt_correction_T_min 0.765980 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Bruker Sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15407 _diffrn_reflns_av_R_equivalents 0.0535 _diffrn_reflns_av_sigmaI/netI 0.0404 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 28.01 _reflns_number_total 3097 _reflns_number_gt 2571 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0767P)^2^+1.0418P] 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 3097 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0569 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1286 _refine_ls_wR_factor_gt 0.1234 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 0.57183(3) 0.27996(3) 0.52758(3) 0.02176(15) Uani 1 1 d . . . O1 O 0.58966(13) 0.15835(14) 0.56621(15) 0.0342(4) Uani 1 1 d . . . O2 O 0.58882(13) 0.29497(15) 0.42933(14) 0.0331(4) Uani 1 1 d . . . O3 O 0.43453(11) 0.29462(13) 0.46272(13) 0.0249(4) Uani 1 1 d . . . N1 N 0.70558(13) 0.33673(16) 0.64190(15) 0.0218(4) Uani 1 1 d . . . N2 N 0.54754(13) 0.40342(15) 0.60691(14) 0.0204(4) Uani 1 1 d . . . N3 N 0.45502(13) 0.42868(16) 0.57728(15) 0.0230(4) Uani 1 1 d . . . C1 C 0.78689(18) 0.2949(2) 0.6571(2) 0.0272(5) Uani 1 1 d . . . H1A H 0.7847 0.2394 0.6126 0.033 Uiso 1 1 calc R . . C2 C 0.87348(17) 0.3293(2) 0.7349(2) 0.0325(6) Uani 1 1 d . . . H2A H 0.9299 0.2965 0.7450 0.039 Uiso 1 1 calc R . . C3 C 0.87778(17) 0.4116(2) 0.7983(2) 0.0313(6) Uani 1 1 d . . . H3A H 0.9371 0.4361 0.8525 0.038 Uiso 1 1 calc R . . C4 C 0.79432(17) 0.4579(2) 0.78154(19) 0.0262(5) Uani 1 1 d . . . H4A H 0.7956 0.5160 0.8231 0.031 Uiso 1 1 calc R . . C5 C 0.70910(16) 0.41842(18) 0.70348(17) 0.0218(5) Uani 1 1 d . . . C6 C 0.61598(16) 0.45671(18) 0.68053(18) 0.0212(5) Uani 1 1 d . . . C7 C 0.60276(17) 0.5468(2) 0.7365(2) 0.0284(5) Uani 1 1 d . . . H7A H 0.5350 0.5591 0.7087 0.043 Uiso 1 1 calc R . . H7B H 0.6318 0.6105 0.7267 0.043 Uiso 1 1 calc R . . H7C H 0.6328 0.5303 0.8110 0.043 Uiso 1 1 calc R . . C8 C 0.40104(16) 0.36526(18) 0.49978(17) 0.0208(5) Uani 1 1 d . . . C9 C 0.29743(15) 0.37410(18) 0.45314(17) 0.0208(5) Uani 1 1 d . . . C10 C 0.25775(17) 0.45637(19) 0.48216(18) 0.0246(5) Uani 1 1 d . . . H10A H 0.2972 0.5102 0.5281 0.030 Uiso 1 1 calc R . . C11 C 0.16140(17) 0.4594(2) 0.44417(19) 0.0289(6) Uani 1 1 d . . . H11A H 0.1346 0.5153 0.4641 0.035 Uiso 1 1 calc R . . C12 C 0.10358(17) 0.3812(2) 0.37710(19) 0.0293(6) Uani 1 1 d . . . H12A H 0.0375 0.3823 0.3529 0.035 Uiso 1 1 calc R . . C13 C 0.14175(18) 0.3015(2) 0.3452(2) 0.0295(6) Uani 1 1 d . . . H13A H 0.1016 0.2494 0.2973 0.035 Uiso 1 1 calc R . . C14 C 0.23897(18) 0.29769(19) 0.38328(19) 0.0253(5) Uani 1 1 d . . . H14A H 0.2652 0.2429 0.3615 0.030 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 0.0228(2) 0.0235(2) 0.0192(2) -0.00210(15) 0.01065(18) 0.00280(15) O1 0.0319(9) 0.0254(10) 0.0388(11) 0.0003(8) 0.0126(8) 0.0025(8) O2 0.0290(10) 0.0489(12) 0.0236(9) -0.0015(8) 0.0146(8) 0.0063(8) O3 0.0228(9) 0.0292(10) 0.0230(9) -0.0066(7) 0.0115(7) 0.0004(7) N1 0.0235(10) 0.0224(10) 0.0210(10) 0.0030(8) 0.0121(8) 0.0017(8) N2 0.0219(9) 0.0220(10) 0.0179(9) 0.0007(8) 0.0103(8) 0.0027(8) N3 0.0201(9) 0.0277(11) 0.0204(10) -0.0014(8) 0.0095(8) 0.0021(8) C1 0.0272(13) 0.0274(13) 0.0309(13) 0.0031(10) 0.0174(11) 0.0039(10) C2 0.0233(12) 0.0372(15) 0.0385(15) 0.0062(12) 0.0164(12) 0.0044(11) C3 0.0219(12) 0.0383(15) 0.0297(13) 0.0046(11) 0.0098(11) -0.0043(11) C4 0.0275(13) 0.0275(13) 0.0232(12) 0.0018(10) 0.0124(11) -0.0024(10) C5 0.0266(12) 0.0216(11) 0.0185(11) 0.0041(9) 0.0123(10) 0.0018(9) C6 0.0251(11) 0.0223(12) 0.0172(10) 0.0026(9) 0.0112(10) 0.0003(9) C7 0.0272(12) 0.0308(13) 0.0248(12) -0.0073(10) 0.0113(11) 0.0006(10) C8 0.0240(11) 0.0231(12) 0.0165(10) 0.0014(9) 0.0109(9) 0.0014(9) C9 0.0221(11) 0.0252(12) 0.0161(10) 0.0036(9) 0.0102(9) 0.0020(9) C10 0.0270(12) 0.0278(12) 0.0161(11) -0.0002(9) 0.0084(10) 0.0024(10) C11 0.0283(13) 0.0353(14) 0.0223(12) 0.0019(10) 0.0118(11) 0.0085(11) C12 0.0218(12) 0.0408(15) 0.0225(12) 0.0041(11) 0.0088(10) 0.0026(11) C13 0.0252(13) 0.0333(14) 0.0240(12) -0.0016(10) 0.0076(11) -0.0035(10) C14 0.0286(13) 0.0262(12) 0.0205(12) 0.0000(9) 0.0117(10) 0.0020(10) _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 1.6150(19) . ? V1 O2 1.6181(18) . ? V1 O3 1.9548(17) . ? V1 N2 2.1037(19) . ? V1 N1 2.111(2) . ? O3 C8 1.300(3) . ? N1 C1 1.337(3) . ? N1 C5 1.358(3) . ? N2 C6 1.294(3) . ? N2 N3 1.381(3) . ? N3 C8 1.314(3) . ? C1 C2 1.374(4) . ? C2 C3 1.377(4) . ? C3 C4 1.385(4) . ? C4 C5 1.384(3) . ? C5 C6 1.462(3) . ? C6 C7 1.485(3) . ? C8 C9 1.476(3) . ? C9 C14 1.388(3) . ? C9 C10 1.399(3) . ? C10 C11 1.379(3) . ? C11 C12 1.385(4) . ? C12 C13 1.384(4) . ? C13 C14 1.393(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 O1 V1 O2 110.35(10) . . ? O1 V1 O3 102.97(9) . . ? O2 V1 O3 102.29(8) . . ? O1 V1 N2 124.03(9) . . ? O2 V1 N2 125.17(9) . . ? O3 V1 N2 73.56(7) . . ? O1 V1 N1 96.19(9) . . ? O2 V1 N1 96.29(9) . . ? O3 V1 N1 146.51(7) . . ? N2 V1 N1 72.96(7) . . ? C8 O3 V1 118.39(15) . . ? C1 N1 C5 118.7(2) . . ? C1 N1 V1 122.81(17) . . ? C5 N1 V1 118.54(15) . . ? C6 N2 N3 119.62(19) . . ? C6 N2 V1 122.19(15) . . ? N3 N2 V1 118.18(14) . . ? C8 N3 N2 106.70(18) . . ? N1 C1 C2 122.3(2) . . ? C1 C2 C3 119.5(2) . . ? C2 C3 C4 119.0(2) . . ? C5 C4 C3 119.0(2) . . ? N1 C5 C4 121.6(2) . . ? N1 C5 C6 113.7(2) . . ? C4 C5 C6 124.7(2) . . ? N2 C6 C5 112.5(2) . . ? N2 C6 C7 124.4(2) . . ? C5 C6 C7 123.1(2) . . ? O3 C8 N3 123.1(2) . . ? O3 C8 C9 118.5(2) . . ? N3 C8 C9 118.4(2) . . ? C14 C9 C10 119.6(2) . . ? C14 C9 C8 119.8(2) . . ? C10 C9 C8 120.5(2) . . ? C11 C10 C9 120.1(2) . . ? C10 C11 C12 120.2(2) . . ? C13 C12 C11 120.2(2) . . ? C12 C13 C14 120.0(2) . . ? C9 C14 C13 119.9(2) . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 28.01 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.742 _refine_diff_density_min -0.511 _refine_diff_density_rms 0.093 data_3vinh _database_code_CSD 182867 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H11 N4 O3 V' _chemical_formula_weight 322.20 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 C2/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 14.280(5) _cell_length_b 6.834(2) _cell_length_c 14.297(5) _cell_angle_alpha 90.00 _cell_angle_beta 106.507(6) _cell_angle_gamma 90.00 _cell_volume 1337.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1097 _cell_measurement_theta_min 2.924 _cell_measurement_theta_max 23.281 _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.600 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.757 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.530563 _exptl_absorpt_correction_T_max 0.801392 _exptl_absorpt_process_details 'Bruker 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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3777 _diffrn_reflns_av_R_equivalents 0.1061 _diffrn_reflns_av_sigmaI/netI 0.0794 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 25.06 _reflns_number_total 1299 _reflns_number_gt 957 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0782P)^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 Constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1299 _refine_ls_number_parameters 130 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0771 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1442 _refine_ls_wR_factor_gt 0.1325 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 0.11748(5) 0.0000 0.19612(5) 0.0429(4) Uani 1 2 d S . . O1 O 0.05500(17) 0.1938(4) 0.15405(17) 0.0599(8) Uani 1 1 d . . . O2 O 0.1198(2) 0.0000 0.3339(2) 0.0652(12) Uani 1 2 d S . . N1 N 0.2002(3) 0.0000 0.0953(3) 0.0389(9) Uani 1 2 d S . . N2 N 0.2658(3) 0.0000 0.2775(3) 0.0469(11) Uani 1 2 d S . . N3 N 0.2885(3) 0.0000 0.3783(3) 0.0606(13) Uani 1 2 d S . . N4 N 0.2071(4) 0.0000 0.6996(4) 0.0842(18) Uani 1 2 d S . . C1 C 0.1591(4) 0.0000 -0.0005(3) 0.0467(12) Uani 1 2 d S . . H1A H 0.0914 0.0000 -0.0240 0.056 Uiso 1 2 calc SR . . C2 C 0.2142(4) 0.0000 -0.0673(4) 0.0538(14) Uani 1 2 d S . . H2A H 0.1835 0.0000 -0.1340 0.065 Uiso 1 2 calc SR . . C3 C 0.3135(5) 0.0000 -0.0330(4) 0.0548(15) Uani 1 2 d S . . H3A H 0.3515 0.0000 -0.0762 0.066 Uiso 1 2 calc SR . . C4 C 0.3577(4) 0.0000 0.0673(4) 0.0479(13) Uani 1 2 d S . . H4A H 0.4254 0.0000 0.0923 0.057 Uiso 1 2 calc SR . . C5 C 0.2981(3) 0.0000 0.1294(3) 0.0406(11) Uani 1 2 d S . . C6 C 0.3350(4) 0.0000 0.2355(4) 0.0464(13) Uani 1 2 d S . . C7 C 0.4419(4) 0.0000 0.2888(4) 0.0675(18) Uani 1 2 d S . . H7A H 0.4502 0.0000 0.3578 0.101 Uiso 1 2 calc SR . . H7B H 0.4719 0.1147 0.2713 0.101 Uiso 0.50 1 calc PR . . H7C H 0.4719 -0.1147 0.2713 0.101 Uiso 0.50 1 calc PR . . C8 C 0.2045(4) 0.0000 0.3984(4) 0.0639(17) Uani 1 2 d S . . C9 C 0.2068(4) 0.0000 0.5032(4) 0.0723(19) Uani 1 2 d S . . C10 C 0.2931(4) 0.0000 0.5783(4) 0.0579(15) Uani 1 2 d S A . H10A H 0.3530 0.0000 0.5646 0.070 Uiso 1 2 calc SR . . C11 C 0.2890(4) 0.0000 0.6732(4) 0.0652(16) Uani 1 2 d S A . H11A H 0.3479 0.0000 0.7224 0.078 Uiso 1 2 calc SR . . C12 C 0.1271(6) -0.0576(11) 0.6279(5) 0.058(3) Uani 0.50 1 d P A -1 H12A H 0.0724 -0.0970 0.6462 0.069 Uiso 0.50 1 calc PR A -1 C13 C 0.1211(5) -0.0616(10) 0.5290(5) 0.054(3) Uani 0.50 1 d P A -1 H13A H 0.0648 -0.1019 0.4822 0.065 Uiso 0.50 1 calc PR A -1 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 0.0323(5) 0.0726(7) 0.0257(5) 0.000 0.0111(4) 0.000 O1 0.0518(16) 0.0839(19) 0.0431(16) -0.0028(13) 0.0120(13) 0.0210(14) O2 0.0285(18) 0.146(4) 0.0231(18) 0.000 0.0101(16) 0.000 N1 0.045(2) 0.049(2) 0.024(2) 0.000 0.0132(19) 0.000 N2 0.030(2) 0.085(3) 0.028(2) 0.000 0.0119(18) 0.000 N3 0.036(2) 0.125(4) 0.023(2) 0.000 0.0119(19) 0.000 N4 0.069(4) 0.157(6) 0.032(3) 0.000 0.022(3) 0.000 C1 0.051(3) 0.060(3) 0.029(3) 0.000 0.009(2) 0.000 C2 0.078(4) 0.059(3) 0.028(3) 0.000 0.020(3) 0.000 C3 0.080(4) 0.054(3) 0.044(3) 0.000 0.041(3) 0.000 C4 0.051(3) 0.059(3) 0.043(3) 0.000 0.029(3) 0.000 C5 0.041(3) 0.051(3) 0.036(3) 0.000 0.020(2) 0.000 C6 0.038(3) 0.069(4) 0.038(3) 0.000 0.020(2) 0.000 C7 0.034(3) 0.125(5) 0.045(3) 0.000 0.014(3) 0.000 C8 0.042(3) 0.122(5) 0.032(3) 0.000 0.017(3) 0.000 C9 0.049(3) 0.149(6) 0.023(3) 0.000 0.017(3) 0.000 C10 0.046(3) 0.102(5) 0.029(3) 0.000 0.016(2) 0.000 C11 0.058(4) 0.106(5) 0.029(3) 0.000 0.008(3) 0.000 C12 0.064(4) 0.079(9) 0.044(4) 0.007(4) 0.037(4) 0.007(4) C13 0.048(4) 0.085(9) 0.034(4) 0.000(3) 0.019(3) 0.007(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 O1 1.615(3) 6 ? V1 O1 1.615(3) . ? V1 O2 1.961(3) . ? V1 N2 2.107(4) . ? V1 N1 2.107(3) . ? O2 C8 1.296(6) . ? N1 C1 1.328(6) . ? N1 C5 1.344(6) . ? N2 C6 1.294(5) . ? N2 N3 1.384(5) . ? N3 C8 1.311(6) . ? N4 C11 1.327(7) . ? N4 C12 1.359(9) . ? N4 C12 1.359(9) 6 ? C1 C2 1.399(6) . ? C1 H1A 0.9300 . ? C2 C3 1.362(8) . ? C2 H2A 0.9300 . ? C3 C4 1.393(7) . ? C3 H3A 0.9300 . ? C4 C5 1.392(5) . ? C4 H4A 0.9300 . ? C5 C6 1.458(6) . ? C6 C7 1.500(7) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.490(6) . ? C9 C10 1.385(8) . ? C9 C13 1.438(8) 6 ? C9 C13 1.438(8) . ? C10 C11 1.375(7) . ? C10 H10A 0.9300 . ? C11 H11A 0.9300 . ? C12 C13 1.392(9) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? 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 O1 110.22(19) 6 . ? O1 V1 O2 102.95(10) 6 . ? O1 V1 O2 102.95(10) . . ? O1 V1 N2 124.62(10) 6 . ? O1 V1 N2 124.62(10) . . ? O2 V1 N2 73.59(14) . . ? O1 V1 N1 95.92(11) 6 . ? O1 V1 N1 95.92(11) . . ? O2 V1 N1 146.55(15) . . ? N2 V1 N1 72.97(15) . . ? C8 O2 V1 117.4(3) . . ? C1 N1 C5 118.9(4) . . ? C1 N1 V1 122.4(3) . . ? C5 N1 V1 118.7(3) . . ? C6 N2 N3 119.9(4) . . ? C6 N2 V1 121.6(3) . . ? N3 N2 V1 118.5(3) . . ? C8 N3 N2 105.6(4) . . ? C11 N4 C12 114.0(5) . . ? C11 N4 C12 114.0(5) . 6 ? C12 N4 C12 33.6(6) . 6 ? N1 C1 C2 122.3(5) . . ? N1 C1 H1A 118.8 . . ? C2 C1 H1A 118.8 . . ? C3 C2 C1 119.0(5) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? C2 C3 C4 119.4(4) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? C5 C4 C3 118.4(5) . . ? C5 C4 H4A 120.8 . . ? C3 C4 H4A 120.8 . . ? N1 C5 C4 122.0(4) . . ? N1 C5 C6 114.1(3) . . ? C4 C5 C6 123.9(4) . . ? N2 C6 C5 112.7(4) . . ? N2 C6 C7 124.4(4) . . ? C5 C6 C7 122.9(4) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O2 C8 N3 124.9(5) . . ? O2 C8 C9 117.7(4) . . ? N3 C8 C9 117.4(5) . . ? C10 C9 C13 115.8(5) . 6 ? C10 C9 C13 115.8(5) . . ? C13 C9 C13 34.0(6) 6 . ? C10 C9 C8 122.7(5) . . ? C13 C9 C8 118.8(5) 6 . ? C13 C9 C8 118.8(5) . . ? C11 C10 C9 119.2(5) . . ? C11 C10 H10A 120.4 . . ? C9 C10 H10A 120.4 . . ? N4 C11 C10 124.6(6) . . ? N4 C11 H11A 117.7 . . ? C10 C11 H11A 117.7 . . ? N4 C12 C13 124.5(6) . . ? N4 C12 H12A 117.7 . . ? C13 C12 H12A 117.7 . . ? C12 C13 C9 116.4(6) . . ? C12 C13 H13A 121.8 . . ? C9 C13 H13A 121.8 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.451 _refine_diff_density_min -0.772 _refine_diff_density_rms 0.104