# 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_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H22 N2 O8 V2' _chemical_formula_weight 472.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' V V 0.0687 2.1097 '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 1 21/n 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.4465(5) _cell_length_b 11.4952(7) _cell_length_c 12.5252(8) _cell_angle_alpha 90.00 _cell_angle_beta 96.512(6) _cell_angle_gamma 90.00 _cell_volume 922.18(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 2240 _cell_measurement_theta_min 3.5488 _cell_measurement_theta_max 76.9254 _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.541 _exptl_crystal_size_mid 0.302 _exptl_crystal_size_min 0.179 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.701 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 8.942 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.33324 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 100(1) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 10.4223 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3446 _diffrn_reflns_av_R_equivalents 0.0397 _diffrn_reflns_av_unetI/netI 0.0296 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 5.24 _diffrn_reflns_theta_max 77.13 _reflns_number_total 1888 _reflns_number_gt 1847 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WINGX 1.80.05' _computing_publication_material 'WINGX 1.80.05' _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^)+(0.1254P)^2^+0.2339P] 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 SHELXL _refine_ls_extinction_coef 0.0047(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1888 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0557 _refine_ls_wR_factor_ref 0.1502 _refine_ls_wR_factor_gt 0.1494 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 C1 C 0.1393(3) 0.16380(19) 0.95372(17) 0.0197(5) Uani 1 1 d . . . H1A H 0.0753 0.1019 0.9912 0.024 Uiso 1 1 calc R . . H1B H 0.1774 0.2262 1.0043 0.024 Uiso 1 1 calc R . . C8 C 0.1534(3) 0.56235(18) 0.95557(16) 0.0165(4) Uani 1 1 d . . . H8 H 0.2565 0.6036 0.9256 0.020 Uiso 1 1 calc R . . C4 C -0.1699(3) 0.16257(19) 0.68612(18) 0.0217(5) Uani 1 1 d . . . H4A H -0.2016 0.1000 0.6349 0.026 Uiso 1 1 calc R . . H4B H -0.2938 0.2103 0.6868 0.026 Uiso 1 1 calc R . . C7 C 0.0768(3) 0.45908(17) 0.90746(17) 0.0160(4) Uani 1 1 d . . . C5 C -0.1676(3) 0.28598(16) 0.90022(19) 0.0174(5) Uani 1 1 d . . . H5A H -0.2437 0.2450 0.9511 0.021 Uiso 1 1 calc R . . H5B H -0.2663 0.3066 0.8389 0.021 Uiso 1 1 calc R . . C6 C -0.0772(3) 0.39551(18) 0.95194(16) 0.0166(4) Uani 1 1 d . . . C3 C -0.1085(3) 0.11251(18) 0.79662(18) 0.0197(5) Uani 1 1 d . . . H3A H -0.2310 0.0843 0.8269 0.024 Uiso 1 1 calc R . . H3B H -0.0124 0.0481 0.7927 0.024 Uiso 1 1 calc R . . C2 C 0.3318(3) 0.11861(19) 0.90758(18) 0.0219(5) Uani 1 1 d . . . H2A H 0.4485 0.1152 0.9637 0.026 Uiso 1 1 calc R . . H2B H 0.3058 0.0406 0.8796 0.026 Uiso 1 1 calc R . . V1 V 0.20548(5) 0.29176(3) 0.74793(3) 0.0159(2) Uani 1 1 d . . . O1 O 0.3815(3) 0.19380(14) 0.82356(15) 0.0209(4) Uani 1 1 d . . . O2 O -0.0023(3) 0.23146(17) 0.65484(14) 0.0210(4) Uani 1 1 d . . . N1 N -0.0077(3) 0.20686(13) 0.86406(16) 0.0166(4) Uani 1 1 d . . . O4 O 0.3550(3) 0.33819(14) 0.66240(13) 0.0237(4) Uani 1 1 d . . . O3 O 0.1541(2) 0.42628(13) 0.81522(12) 0.0210(4) 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 C1 0.0203(10) 0.0189(11) 0.0189(10) 0.0005(8) -0.0014(8) -0.0005(8) C8 0.0164(9) 0.0154(9) 0.0177(10) 0.0008(7) 0.0016(7) 0.0003(7) C4 0.0179(10) 0.0238(11) 0.0224(11) -0.0054(8) -0.0028(8) -0.0014(8) C7 0.0181(9) 0.0140(9) 0.0157(9) -0.0013(7) 0.0011(7) 0.0009(7) C5 0.0152(10) 0.0148(11) 0.0218(11) -0.0030(7) 0.0006(8) -0.0007(6) C6 0.0158(9) 0.0155(9) 0.0179(9) -0.0018(7) -0.0004(7) 0.0016(7) C3 0.0199(10) 0.0160(9) 0.0226(10) -0.0051(8) -0.0009(8) -0.0039(8) C2 0.0204(11) 0.0205(11) 0.0235(11) 0.0010(8) -0.0030(8) -0.0002(8) V1 0.0165(4) 0.0148(3) 0.0161(3) -0.00208(10) 0.0010(2) -0.00055(10) O1 0.0165(8) 0.0198(7) 0.0255(9) 0.0007(6) -0.0007(6) 0.0006(6) O2 0.0200(8) 0.0244(7) 0.0179(8) -0.0024(6) -0.0014(6) -0.0007(7) N1 0.0164(9) 0.0146(10) 0.0179(10) -0.0037(5) -0.0020(7) -0.0007(6) O4 0.0277(9) 0.0210(9) 0.0238(8) -0.0037(6) 0.0091(6) -0.0011(6) O3 0.0285(8) 0.0163(8) 0.0193(7) -0.0026(6) 0.0069(6) -0.0025(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 C1 N1 1.471(3) . ? C1 C2 1.519(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C8 C6 1.395(3) 3_567 ? C8 C7 1.396(3) . ? C8 H8 0.9300 . ? C4 O2 1.430(3) . ? C4 C3 1.510(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C7 O3 1.362(2) . ? C7 C6 1.398(3) . ? C5 N1 1.483(3) . ? C5 C6 1.503(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C8 1.395(3) 3_567 ? C3 N1 1.479(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C2 O1 1.426(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? V1 O4 1.6112(16) . ? V1 O1 1.7915(17) . ? V1 O3 1.8095(15) . ? V1 O2 1.8109(17) . ? V1 N1 2.326(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 107.94(18) . . ? 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 . . ? C6 C8 C7 120.86(19) 3_567 . ? C6 C8 H8 119.6 3_567 . ? C7 C8 H8 119.6 . . ? O2 C4 C3 109.57(17) . . ? O2 C4 H4A 109.8 . . ? C3 C4 H4A 109.8 . . ? O2 C4 H4B 109.8 . . ? C3 C4 H4B 109.8 . . ? H4A C4 H4B 108.2 . . ? O3 C7 C8 117.12(18) . . ? O3 C7 C6 122.54(19) . . ? C8 C7 C6 120.32(19) . . ? N1 C5 C6 113.35(18) . . ? N1 C5 H5A 108.9 . . ? C6 C5 H5A 108.9 . . ? N1 C5 H5B 108.9 . . ? C6 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? C8 C6 C7 118.82(19) 3_567 . ? C8 C6 C5 119.53(19) 3_567 . ? C7 C6 C5 121.61(19) . . ? N1 C3 C4 107.25(17) . . ? N1 C3 H3A 110.3 . . ? C4 C3 H3A 110.3 . . ? N1 C3 H3B 110.3 . . ? C4 C3 H3B 110.3 . . ? H3A C3 H3B 108.5 . . ? O1 C2 C1 109.58(18) . . ? O1 C2 H2A 109.8 . . ? C1 C2 H2A 109.8 . . ? O1 C2 H2B 109.8 . . ? C1 C2 H2B 109.8 . . ? H2A C2 H2B 108.2 . . ? O4 V1 O1 99.72(9) . . ? O4 V1 O3 100.46(8) . . ? O1 V1 O3 115.42(8) . . ? O4 V1 O2 98.81(8) . . ? O1 V1 O2 118.53(7) . . ? O3 V1 O2 117.77(8) . . ? O4 V1 N1 174.41(7) . . ? O1 V1 N1 77.84(8) . . ? O3 V1 N1 85.12(6) . . ? O2 V1 N1 78.22(7) . . ? C2 O1 V1 126.11(14) . . ? C4 O2 V1 124.21(14) . . ? C1 N1 C3 113.12(16) . . ? C1 N1 C5 112.52(18) . . ? C3 N1 C5 110.38(18) . . ? C1 N1 V1 104.10(13) . . ? C3 N1 V1 101.72(13) . . ? C5 N1 V1 114.45(12) . . ? C7 O3 V1 137.34(13) . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 74.33 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.747 _refine_diff_density_min -0.798 _refine_diff_density_rms 0.140 _database_code_depnum_ccdc_archive 'CCDC 928111' ####################################################################### # # 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_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H34 N2 O10 S2 V2' _chemical_formula_weight 628.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' V V 0.0687 2.1097 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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 1 21/a 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 13.3994(8) _cell_length_b 6.7080(3) _cell_length_c 14.5850(8) _cell_angle_alpha 90.00 _cell_angle_beta 110.353(7) _cell_angle_gamma 90.00 _cell_volume 1229.10(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 2339 _cell_measurement_theta_min 3.2292 _cell_measurement_theta_max 76.9109 _exptl_crystal_description plate _exptl_crystal_colour 'dark blue' _exptl_crystal_size_max 0.335 _exptl_crystal_size_mid 0.122 _exptl_crystal_size_min 0.036 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.698 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 652 _exptl_absorpt_coefficient_mu 8.485 _exptl_absorpt_correction_T_min 0.55425 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(1) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 10.4223 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4865 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_unetI/netI 0.0340 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.2292 _diffrn_reflns_theta_max 76.9109 _reflns_number_total 2546 _reflns_number_gt 2348 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WINGX 1.80.05' _computing_publication_material 'WINGX 1.80.05' _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^)+(0.0656P)^2^+0.5371P] 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 2546 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0414 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.1082 _refine_ls_wR_factor_gt 0.1042 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 0.75973(3) 0.14406(6) 0.72085(3) 0.01645(14) Uani 1 1 d . . . S1 S 0.83741(4) 0.43591(9) 0.59609(4) 0.02186(16) Uani 1 1 d . . . O4 O 0.74471(13) 0.0196(3) 0.62242(12) 0.0250(4) Uani 1 1 d . . . O2 O 0.67397(13) 0.0007(3) 0.77212(13) 0.0239(4) Uani 1 1 d . . . O5 O 0.86573(13) 0.3550(2) 0.70061(12) 0.0210(4) Uani 1 1 d . . . O3 O 0.88613(12) 0.0239(2) 0.80260(11) 0.0192(3) Uani 1 1 d . . . N1 N 0.77426(15) 0.3411(3) 0.85565(14) 0.0170(4) Uani 1 1 d . . . O1 O 0.65715(13) 0.3369(2) 0.66777(12) 0.0212(4) Uani 1 1 d . . . C5 C 0.88511(18) 0.3670(3) 0.92355(16) 0.0171(4) Uani 1 1 d . . . H00A H 0.8846 0.4499 0.9779 0.021 Uiso 1 1 calc R . . H00B H 0.9255 0.4366 0.8897 0.021 Uiso 1 1 calc R . . C1 C 0.73159(18) 0.5374(3) 0.81373(17) 0.0203(5) Uani 1 1 d . . . H01A H 0.7874 0.6152 0.8026 0.024 Uiso 1 1 calc R . . H01B H 0.7068 0.6099 0.8593 0.024 Uiso 1 1 calc R . . C4 C 0.6259(2) 0.1078(4) 0.82923(19) 0.0262(5) Uani 1 1 d . . . H01C H 0.5956 0.0151 0.8634 0.031 Uiso 1 1 calc R . . H01D H 0.5687 0.1897 0.7869 0.031 Uiso 1 1 calc R . . C3 C 0.70684(17) 0.2390(4) 0.90268(16) 0.0204(4) Uani 1 1 d . . . H01E H 0.6704 0.3372 0.9285 0.024 Uiso 1 1 calc R . . H01F H 0.7511 0.1584 0.9567 0.024 Uiso 1 1 calc R . . C6 C 0.94054(17) 0.1736(3) 0.96325(16) 0.0162(4) Uani 1 1 d . . . C7 C 0.94015(17) 0.0172(3) 0.89900(16) 0.0159(4) Uani 1 1 d . . . C2 C 0.63954(19) 0.5076(4) 0.71716(18) 0.0227(5) Uani 1 1 d . . . H01G H 0.5736 0.4920 0.7299 0.027 Uiso 1 1 calc R . . H01H H 0.6329 0.6242 0.6761 0.027 Uiso 1 1 calc R . . C8 C 1.00111(17) -0.1532(3) 0.93737(17) 0.0172(4) Uani 1 1 d . . . H1 H 1.0026 -0.2559 0.8951 0.021 Uiso 1 1 calc R . . C9 C 0.9150(2) 0.6575(4) 0.6134(2) 0.0309(6) Uani 1 1 d . . . H5A H 0.8842 0.7585 0.6420 0.046 Uiso 1 1 calc R . . H5B H 0.9162 0.7032 0.5515 0.046 Uiso 1 1 calc R . . H5C H 0.9863 0.6302 0.6562 0.046 Uiso 1 1 calc R . . C10 C 0.9115(2) 0.2805(4) 0.54339(18) 0.0281(5) Uani 1 1 d . . . H7A H 0.8786 0.1515 0.5295 0.042 Uiso 1 1 calc R . . H7B H 0.9830 0.2667 0.5885 0.042 Uiso 1 1 calc R . . H7C H 0.9126 0.3398 0.4839 0.042 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 0.0155(2) 0.0182(2) 0.0149(2) -0.00001(13) 0.00433(15) 0.00007(13) S1 0.0176(3) 0.0294(3) 0.0197(3) 0.0073(2) 0.0079(2) 0.0025(2) O4 0.0229(8) 0.0289(9) 0.0205(8) -0.0027(7) 0.0040(7) 0.0011(7) O2 0.0254(8) 0.0220(8) 0.0260(8) -0.0009(7) 0.0110(7) -0.0053(7) O5 0.0184(8) 0.0273(9) 0.0172(7) 0.0042(6) 0.0059(6) -0.0019(6) O3 0.0211(8) 0.0207(8) 0.0146(7) -0.0001(6) 0.0048(6) 0.0032(6) N1 0.0164(9) 0.0175(9) 0.0160(8) 0.0015(7) 0.0043(7) 0.0017(7) O1 0.0171(8) 0.0239(8) 0.0195(8) 0.0009(6) 0.0025(6) 0.0012(6) C5 0.0177(10) 0.0153(10) 0.0167(10) -0.0019(7) 0.0040(8) 0.0001(7) C1 0.0217(11) 0.0179(10) 0.0196(10) 0.0010(8) 0.0052(9) 0.0043(9) C4 0.0237(12) 0.0316(13) 0.0251(11) 0.0022(10) 0.0108(10) -0.0039(10) C3 0.0168(9) 0.0287(12) 0.0174(9) 0.0016(9) 0.0081(8) 0.0003(9) C6 0.0151(9) 0.0150(9) 0.0191(10) -0.0003(8) 0.0070(8) -0.0006(7) C7 0.0146(9) 0.0184(10) 0.0143(9) -0.0002(8) 0.0045(8) -0.0007(8) C2 0.0201(10) 0.0243(11) 0.0218(11) 0.0023(9) 0.0047(9) 0.0062(9) C8 0.0173(10) 0.0158(10) 0.0196(10) -0.0021(8) 0.0079(9) -0.0010(7) C9 0.0322(14) 0.0273(13) 0.0389(14) 0.0069(11) 0.0196(12) -0.0012(10) C10 0.0260(12) 0.0355(14) 0.0251(11) 0.0038(11) 0.0118(10) 0.0058(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag V1 O4 1.6117(17) . ? V1 O2 1.8446(17) . ? V1 O1 1.8498(17) . ? V1 O3 1.8801(16) . ? V1 O5 2.0974(17) . ? V1 N1 2.3206(19) . ? S1 O5 1.5361(17) . ? S1 C9 1.781(3) . ? S1 C10 1.787(3) . ? O2 C4 1.414(3) . ? O3 C7 1.340(3) . ? N1 C3 1.479(3) . ? N1 C1 1.480(3) . ? N1 C5 1.481(3) . ? O1 C2 1.416(3) . ? C5 C6 1.507(3) . ? C5 H00A 0.9700 . ? C5 H00B 0.9700 . ? C1 C2 1.529(3) . ? C1 H01A 0.9700 . ? C1 H01B 0.9700 . ? C4 C3 1.513(3) . ? C4 H01C 0.9700 . ? C4 H01D 0.9700 . ? C3 H01E 0.9700 . ? C3 H01F 0.9700 . ? C6 C8 1.394(3) 3_757 ? C6 C7 1.406(3) . ? C7 C8 1.403(3) . ? C2 H01G 0.9700 . ? C2 H01H 0.9700 . ? C8 C6 1.394(3) 3_757 ? C8 H1 0.9300 . ? C9 H5A 0.9600 . ? C9 H5B 0.9600 . ? C9 H5C 0.9600 . ? C10 H7A 0.9600 . ? C10 H7B 0.9600 . ? C10 H7C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 V1 O2 100.87(9) . . ? O4 V1 O1 98.35(8) . . ? O2 V1 O1 93.28(8) . . ? O4 V1 O3 98.55(8) . . ? O2 V1 O3 94.03(8) . . ? O1 V1 O3 159.96(8) . . ? O4 V1 O5 96.03(8) . . ? O2 V1 O5 163.09(7) . . ? O1 V1 O5 84.85(7) . . ? O3 V1 O5 82.74(7) . . ? O4 V1 N1 175.95(8) . . ? O2 V1 N1 80.45(7) . . ? O1 V1 N1 77.72(7) . . ? O3 V1 N1 85.14(7) . . ? O5 V1 N1 82.73(7) . . ? O5 S1 C9 102.90(12) . . ? O5 S1 C10 103.79(11) . . ? C9 S1 C10 99.45(13) . . ? C4 O2 V1 116.71(15) . . ? S1 O5 V1 115.62(9) . . ? C7 O3 V1 135.95(14) . . ? C3 N1 C1 113.15(18) . . ? C3 N1 C5 112.11(17) . . ? C1 N1 C5 109.00(17) . . ? C3 N1 V1 104.14(13) . . ? C1 N1 V1 104.49(13) . . ? C5 N1 V1 113.72(13) . . ? C2 O1 V1 125.72(14) . . ? N1 C5 C6 113.70(18) . . ? N1 C5 H00A 108.8 . . ? C6 C5 H00A 108.8 . . ? N1 C5 H00B 108.8 . . ? C6 C5 H00B 108.8 . . ? H00A C5 H00B 107.7 . . ? N1 C1 C2 109.64(19) . . ? N1 C1 H01A 109.7 . . ? C2 C1 H01A 109.7 . . ? N1 C1 H01B 109.7 . . ? C2 C1 H01B 109.7 . . ? H01A C1 H01B 108.2 . . ? O2 C4 C3 110.6(2) . . ? O2 C4 H01C 109.5 . . ? C3 C4 H01C 109.5 . . ? O2 C4 H01D 109.5 . . ? C3 C4 H01D 109.5 . . ? H01C C4 H01D 108.1 . . ? N1 C3 C4 110.13(18) . . ? N1 C3 H01E 109.6 . . ? C4 C3 H01E 109.6 . . ? N1 C3 H01F 109.6 . . ? C4 C3 H01F 109.6 . . ? H01E C3 H01F 108.1 . . ? C8 C6 C7 119.4(2) 3_757 . ? C8 C6 C5 120.5(2) 3_757 . ? C7 C6 C5 120.0(2) . . ? O3 C7 C8 118.3(2) . . ? O3 C7 C6 123.3(2) . . ? C8 C7 C6 118.4(2) . . ? O1 C2 C1 110.54(18) . . ? O1 C2 H01G 109.5 . . ? C1 C2 H01G 109.5 . . ? O1 C2 H01H 109.5 . . ? C1 C2 H01H 109.5 . . ? H01G C2 H01H 108.1 . . ? C6 C8 C7 122.2(2) 3_757 . ? C6 C8 H1 118.9 3_757 . ? C7 C8 H1 118.9 . . ? S1 C9 H5A 109.5 . . ? S1 C9 H5B 109.5 . . ? H5A C9 H5B 109.5 . . ? S1 C9 H5C 109.5 . . ? H5A C9 H5C 109.5 . . ? H5B C9 H5C 109.5 . . ? S1 C10 H7A 109.5 . . ? S1 C10 H7B 109.5 . . ? H7A C10 H7B 109.5 . . ? S1 C10 H7C 109.5 . . ? H7A C10 H7C 109.5 . . ? H7B C10 H7C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 74.33 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.440 _refine_diff_density_min -0.491 _refine_diff_density_rms 0.084 _database_code_depnum_ccdc_archive 'CCDC 928112' ####################################################################### # # 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_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H30 N2 O10 V2' _chemical_formula_weight 536.32 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 6.882 _cell_length_b 10.977 _cell_length_c 14.849 _cell_angle_alpha 102.79 _cell_angle_beta 103.34 _cell_angle_gamma 90.03 _cell_volume 1062.8 _cell_formula_units_Z 2 _cell_measurement_temperature 150.0(3) _cell_measurement_reflns_used 2371 _cell_measurement_theta_min 3.1385 _cell_measurement_theta_max 68.5474 _exptl_crystal_description plate _exptl_crystal_colour 'dark blue' _exptl_crystal_size_max 0.106 _exptl_crystal_size_mid 0.042 _exptl_crystal_size_min 0.025 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.676 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 7.907 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.53162 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150.0(3) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4223 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6174 _diffrn_reflns_av_R_equivalents 0.1593 _diffrn_reflns_av_unetI/netI 0.1470 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.1385 _diffrn_reflns_theta_max 68.5474 _reflns_number_total 3632 _reflns_number_gt 2550 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WINGX 1.80.05' _computing_publication_material 'WINGX 1.80.05' _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^)+(0.1462P)^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 3632 _refine_ls_number_parameters 298 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1326 _refine_ls_R_factor_gt 0.0845 _refine_ls_wR_factor_ref 0.2453 _refine_ls_wR_factor_gt 0.2144 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 0.85627(14) 0.07155(8) 0.71423(6) 0.0176(3) Uani 1 1 d . . . V1' V 0.85776(14) 0.57170(8) 0.71412(6) 0.0173(3) Uani 1 1 d . . . O2' O 1.0073(6) 0.7285(4) 0.7687(3) 0.0224(9) Uani 1 1 d . . . O3 O 1.0154(6) 0.0575(4) 0.8305(3) 0.0190(9) Uani 1 1 d . . . O5 O 0.9102(6) -0.1131(4) 0.6698(3) 0.0228(9) Uani 1 1 d D . . O5' O 0.7595(7) 0.3868(4) 0.6696(3) 0.0262(10) Uani 1 1 d D . . O3' O 0.8167(6) 0.5586(4) 0.8309(3) 0.0191(8) Uani 1 1 d . . . O1' O 0.9691(6) 0.5451(4) 0.6116(3) 0.0248(10) Uani 1 1 d . . . O4 O 1.0130(6) 0.1275(4) 0.6666(3) 0.0241(9) Uani 1 1 d . . . N1' N 1.1791(7) 0.5079(4) 0.7786(3) 0.0172(10) Uani 1 1 d . . . N1 N 0.6004(7) 0.0081(5) 0.7789(3) 0.0199(10) Uani 1 1 d . . . O4' O 0.6544(6) 0.6273(4) 0.6666(3) 0.0241(10) Uani 1 1 d . . . O1 O 0.6431(6) 0.0452(4) 0.6117(3) 0.0222(9) Uani 1 1 d . . . C7 C 1.0017(8) 0.0293(5) 0.9123(4) 0.0181(12) Uani 1 1 d . . . C3 C 0.5330(9) 0.1240(6) 0.8314(4) 0.0229(13) Uani 1 1 d . . . H3A H 0.5111 0.1110 0.8909 0.027 Uiso 1 1 calc R . . H3B H 0.4070 0.1446 0.7944 0.027 Uiso 1 1 calc R . . C6 C 0.8356(8) -0.0380(5) 0.9221(4) 0.0157(11) Uani 1 1 d . . . C1' C 1.2471(9) 0.4502(6) 0.6933(4) 0.0240(13) Uani 1 1 d . . . H8A H 1.1932 0.3644 0.6695 0.029 Uiso 1 1 calc R . . H8B H 1.3919 0.4496 0.7082 0.029 Uiso 1 1 calc R . . C5 C 0.6618(8) -0.0842(5) 0.8381(4) 0.0196(12) Uani 1 1 d . . . H4A H 0.6976 -0.1595 0.7986 0.024 Uiso 1 1 calc R . . H4B H 0.5486 -0.1062 0.8611 0.024 Uiso 1 1 calc R . . C8 C 1.1636(8) 0.0637(5) 0.9909(4) 0.0164(11) Uani 1 1 d . . . H7 H 1.2753 0.1055 0.9844 0.020 Uiso 1 1 calc R . . C3' C 1.2980(9) 0.6257(6) 0.8325(4) 0.0250(13) Uani 1 1 d . . . H1A H 1.3897 0.6465 0.7968 0.030 Uiso 1 1 calc R . . H1B H 1.3764 0.6133 0.8928 0.030 Uiso 1 1 calc R . . C4' C 1.1630(8) 0.7325(5) 0.8505(4) 0.0231(13) Uani 1 1 d . . . H2A H 1.1063 0.7268 0.9035 0.028 Uiso 1 1 calc R . . H2B H 1.2404 0.8115 0.8669 0.028 Uiso 1 1 calc R . . C8' C 0.8286(8) 0.5636(5) 0.9920(4) 0.0169(11) Uani 1 1 d . . . H18 H 0.7117 0.6067 0.9861 0.020 Uiso 1 1 calc R . . C6' C 1.0878(8) 0.4624(5) 0.9221(4) 0.0176(11) Uani 1 1 d . . . C7' C 0.9090(8) 0.5290(5) 0.9127(4) 0.0184(12) Uani 1 1 d . . . C5' C 1.1759(8) 0.4169(5) 0.8391(4) 0.0167(11) Uani 1 1 d . . . H15A H 1.1006 0.3414 0.8000 0.020 Uiso 1 1 calc R . . H15B H 1.3119 0.3948 0.8620 0.020 Uiso 1 1 calc R . . C1 C 0.4450(8) -0.0512(6) 0.6932(4) 0.0225(13) Uani 1 1 d . . . H10A H 0.3152 -0.0514 0.7084 0.027 Uiso 1 1 calc R . . H10B H 0.4750 -0.1371 0.6697 0.027 Uiso 1 1 calc R . . C2' C 1.1766(9) 0.5241(7) 0.6196(5) 0.0313(15) Uani 1 1 d . . . H14A H 1.2530 0.6035 0.6373 0.038 Uiso 1 1 calc R . . H14B H 1.1970 0.4787 0.5588 0.038 Uiso 1 1 calc R . . O2 O 0.7606(6) 0.2285(4) 0.7689(3) 0.0210(9) Uani 1 1 d . . . C4 C 0.6875(9) 0.2329(6) 0.8519(4) 0.0241(13) Uani 1 1 d . . . H21A H 0.6265 0.3117 0.8688 0.029 Uiso 1 1 calc R . . H21B H 0.7971 0.2264 0.9047 0.029 Uiso 1 1 calc R . . C2 C 0.4428(9) 0.0240(6) 0.6182(4) 0.0290(14) Uani 1 1 d . . . H22A H 0.3633 -0.0216 0.5571 0.035 Uiso 1 1 calc R . . H22B H 0.3836 0.1034 0.6355 0.035 Uiso 1 1 calc R . . C9 C 0.8940(11) -0.1712(6) 0.5723(4) 0.0318(15) Uani 1 1 d . . . H30A H 0.9252 -0.2574 0.5666 0.048 Uiso 1 1 calc R . . H30B H 0.9858 -0.1291 0.5480 0.048 Uiso 1 1 calc R . . H30C H 0.7600 -0.1663 0.5366 0.048 Uiso 1 1 calc R . . C9' C 0.6788(11) 0.3274(6) 0.5725(4) 0.0314(15) Uani 1 1 d . . . H31A H 0.6411 0.2416 0.5677 0.047 Uiso 1 1 calc R . . H31B H 0.7776 0.3311 0.5368 0.047 Uiso 1 1 calc R . . H31C H 0.5633 0.3694 0.5476 0.047 Uiso 1 1 calc R . . H5' H 0.771(12) 0.361(7) 0.714(4) 0.05(2) Uiso 1 1 d DU . . H5 H 0.954(14) -0.153(8) 0.705(6) 0.08(3) Uiso 1 1 d DU . . 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 0.0188(6) 0.0191(6) 0.0177(6) 0.0061(4) 0.0083(4) 0.0009(4) V1' 0.0171(6) 0.0185(5) 0.0168(6) 0.0058(4) 0.0032(4) -0.0023(4) O2' 0.023(2) 0.018(2) 0.025(2) 0.0061(16) 0.0005(17) -0.0047(16) O3 0.020(2) 0.023(2) 0.019(2) 0.0082(16) 0.0095(16) -0.0033(16) O5 0.029(2) 0.019(2) 0.023(2) 0.0079(17) 0.0086(18) 0.0097(17) O5' 0.038(3) 0.019(2) 0.021(2) 0.0049(18) 0.005(2) -0.0016(18) O3' 0.022(2) 0.020(2) 0.019(2) 0.0066(16) 0.0086(16) 0.0018(16) O1' 0.026(2) 0.027(2) 0.022(2) 0.0083(18) 0.0039(18) -0.0040(18) O4 0.028(2) 0.025(2) 0.025(2) 0.0088(17) 0.0136(18) 0.0006(17) N1' 0.017(2) 0.020(2) 0.015(2) 0.0033(19) 0.0046(19) -0.0030(19) N1 0.019(2) 0.024(2) 0.019(2) 0.004(2) 0.009(2) -0.0010(19) O4' 0.022(2) 0.022(2) 0.029(2) 0.0107(18) 0.0021(18) 0.0020(16) O1 0.025(2) 0.025(2) 0.020(2) 0.0047(17) 0.0107(18) 0.0016(17) C7 0.021(3) 0.020(3) 0.016(3) 0.003(2) 0.011(2) -0.003(2) C3 0.021(3) 0.027(3) 0.028(3) 0.007(2) 0.019(3) 0.008(2) C6 0.016(3) 0.016(3) 0.018(3) 0.003(2) 0.010(2) -0.002(2) C1' 0.020(3) 0.027(3) 0.025(3) 0.005(3) 0.006(2) -0.001(2) C5 0.015(3) 0.023(3) 0.020(3) 0.005(2) 0.003(2) -0.003(2) C8 0.013(2) 0.017(3) 0.020(3) 0.004(2) 0.009(2) 0.000(2) C3' 0.017(3) 0.030(3) 0.025(3) 0.003(3) 0.001(2) -0.005(2) C4' 0.018(3) 0.025(3) 0.026(3) 0.003(2) 0.007(2) -0.002(2) C8' 0.010(3) 0.024(3) 0.017(3) 0.000(2) 0.008(2) -0.003(2) C6' 0.011(3) 0.020(3) 0.020(3) 0.003(2) 0.002(2) 0.001(2) C7' 0.016(3) 0.018(3) 0.017(3) 0.001(2) 0.000(2) -0.001(2) C5' 0.021(3) 0.012(2) 0.019(3) 0.009(2) 0.004(2) 0.003(2) C1 0.017(3) 0.027(3) 0.022(3) 0.004(2) 0.003(2) -0.003(2) C2' 0.025(3) 0.050(4) 0.019(3) 0.002(3) 0.011(3) 0.000(3) O2 0.027(2) 0.016(2) 0.025(2) 0.0052(16) 0.0175(18) 0.0061(16) C4 0.021(3) 0.027(3) 0.027(3) 0.003(3) 0.015(3) 0.006(2) C2 0.026(3) 0.043(4) 0.020(3) 0.008(3) 0.007(2) 0.003(3) C9 0.044(4) 0.028(3) 0.023(3) -0.001(3) 0.013(3) 0.005(3) C9' 0.047(4) 0.024(3) 0.017(3) 0.002(2) -0.003(3) -0.011(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag V1 O4 1.607(4) . ? V1 O1 1.824(4) . ? V1 O3 1.857(4) . ? V1 O2 1.920(4) . ? V1 O5 2.050(4) . ? V1 N1 2.363(5) . ? V1' O4' 1.602(4) . ? V1' O1' 1.826(4) . ? V1' O3' 1.856(4) . ? V1' O2' 1.917(4) . ? V1' O5' 2.052(4) . ? V1' N1' 2.371(4) . ? O2' C4' 1.415(7) . ? O3 C7 1.342(7) . ? O5 C9 1.426(7) . ? O5 H5 0.76(2) . ? O5' C9' 1.423(7) . ? O5' H5' 0.76(2) . ? O3' C7' 1.343(7) . ? O1' C2' 1.429(8) . ? N1' C1' 1.465(8) . ? N1' C5' 1.487(7) . ? N1' C3' 1.490(7) . ? N1 C3 1.473(7) . ? N1 C1 1.480(7) . ? N1 C5 1.484(7) . ? O1 C2 1.427(8) . ? C7 C8 1.396(8) . ? C7 C6 1.413(7) . ? C3 C4 1.530(8) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C6 C8 1.381(8) 2_757 ? C6 C5 1.508(7) . ? C1' C2' 1.497(9) . ? C1' H8A 0.9700 . ? C1' H8B 0.9700 . ? C5 H4A 0.9700 . ? C5 H4B 0.9700 . ? C8 C6 1.381(8) 2_757 ? C8 H7 0.9300 . ? C3' C4' 1.512(8) . ? C3' H1A 0.9700 . ? C3' H1B 0.9700 . ? C4' H2A 0.9700 . ? C4' H2B 0.9700 . ? C8' C6' 1.364(8) 2_767 ? C8' C7' 1.392(8) . ? C8' H18 0.9300 . ? C6' C8' 1.364(8) 2_767 ? C6' C7' 1.426(8) . ? C6' C5' 1.486(8) . ? C5' H15A 0.9700 . ? C5' H15B 0.9700 . ? C1 C2 1.525(8) . ? C1 H10A 0.9700 . ? C1 H10B 0.9700 . ? C2' H14A 0.9700 . ? C2' H14B 0.9700 . ? O2 C4 1.426(7) . ? C4 H21A 0.9700 . ? C4 H21B 0.9700 . ? C2 H22A 0.9700 . ? C2 H22B 0.9700 . ? C9 H30A 0.9600 . ? C9 H30B 0.9600 . ? C9 H30C 0.9600 . ? C9' H31A 0.9600 . ? C9' H31B 0.9600 . ? C9' H31C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 V1 O1 97.5(2) . . ? O4 V1 O3 102.4(2) . . ? O1 V1 O3 159.01(18) . . ? O4 V1 O2 97.0(2) . . ? O1 V1 O2 91.49(18) . . ? O3 V1 O2 92.57(18) . . ? O4 V1 O5 96.6(2) . . ? O1 V1 O5 86.52(18) . . ? O3 V1 O5 84.70(18) . . ? O2 V1 O5 166.38(18) . . ? O4 V1 N1 173.13(19) . . ? O1 V1 N1 78.57(18) . . ? O3 V1 N1 82.21(17) . . ? O2 V1 N1 77.60(17) . . ? O5 V1 N1 88.80(18) . . ? O4' V1' O1' 97.5(2) . . ? O4' V1' O3' 102.8(2) . . ? O1' V1' O3' 158.72(19) . . ? O4' V1' O2' 96.96(19) . . ? O1' V1' O2' 91.57(19) . . ? O3' V1' O2' 92.07(18) . . ? O4' V1' O5' 96.6(2) . . ? O1' V1' O5' 86.42(19) . . ? O3' V1' O5' 85.15(18) . . ? O2' V1' O5' 166.45(18) . . ? O4' V1' N1' 173.08(19) . . ? O1' V1' N1' 78.35(18) . . ? O3' V1' N1' 81.96(17) . . ? O2' V1' N1' 77.74(16) . . ? O5' V1' N1' 88.74(17) . . ? C4' O2' V1' 116.3(3) . . ? C7 O3 V1 140.9(4) . . ? C9 O5 V1 122.5(4) . . ? C9 O5 H5 115(8) . . ? V1 O5 H5 122(8) . . ? C9' O5' V1' 123.2(4) . . ? C9' O5' H5' 130(7) . . ? V1' O5' H5' 107(7) . . ? C7' O3' V1' 142.0(4) . . ? C2' O1' V1' 122.3(4) . . ? C1' N1' C5' 110.8(4) . . ? C1' N1' C3' 112.2(4) . . ? C5' N1' C3' 112.2(4) . . ? C1' N1' V1' 102.4(3) . . ? C5' N1' V1' 113.6(3) . . ? C3' N1' V1' 105.3(3) . . ? C3 N1 C1 111.4(5) . . ? C3 N1 C5 113.0(4) . . ? C1 N1 C5 109.4(4) . . ? C3 N1 V1 105.8(3) . . ? C1 N1 V1 102.8(3) . . ? C5 N1 V1 113.9(3) . . ? C2 O1 V1 123.0(3) . . ? O3 C7 C8 118.3(5) . . ? O3 C7 C6 123.4(5) . . ? C8 C7 C6 118.2(5) . . ? N1 C3 C4 111.2(5) . . ? N1 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? N1 C3 H3B 109.4 . . ? C4 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C8 C6 C7 119.1(5) 2_757 . ? C8 C6 C5 120.3(5) 2_757 . ? C7 C6 C5 120.6(5) . . ? N1' C1' C2' 108.5(5) . . ? N1' C1' H8A 110.0 . . ? C2' C1' H8A 110.0 . . ? N1' C1' H8B 110.0 . . ? C2' C1' H8B 110.0 . . ? H8A C1' H8B 108.4 . . ? N1 C5 C6 113.9(5) . . ? N1 C5 H4A 108.8 . . ? C6 C5 H4A 108.8 . . ? N1 C5 H4B 108.8 . . ? C6 C5 H4B 108.8 . . ? H4A C5 H4B 107.7 . . ? C6 C8 C7 122.6(5) 2_757 . ? C6 C8 H7 118.7 2_757 . ? C7 C8 H7 118.7 . . ? N1' C3' C4' 111.0(5) . . ? N1' C3' H1A 109.4 . . ? C4' C3' H1A 109.4 . . ? N1' C3' H1B 109.4 . . ? C4' C3' H1B 109.4 . . ? H1A C3' H1B 108.0 . . ? O2' C4' C3' 110.4(5) . . ? O2' C4' H2A 109.6 . . ? C3' C4' H2A 109.6 . . ? O2' C4' H2B 109.6 . . ? C3' C4' H2B 109.6 . . ? H2A C4' H2B 108.1 . . ? C6' C8' C7' 123.5(5) 2_767 . ? C6' C8' H18 118.3 2_767 . ? C7' C8' H18 118.3 . . ? C8' C6' C7' 118.5(5) 2_767 . ? C8' C6' C5' 120.6(5) 2_767 . ? C7' C6' C5' 120.8(5) . . ? O3' C7' C8' 119.5(5) . . ? O3' C7' C6' 122.5(5) . . ? C8' C7' C6' 118.0(5) . . ? C6' C5' N1' 114.8(4) . . ? C6' C5' H15A 108.6 . . ? N1' C5' H15A 108.6 . . ? C6' C5' H15B 108.6 . . ? N1' C5' H15B 108.6 . . ? H15A C5' H15B 107.5 . . ? N1 C1 C2 107.8(5) . . ? N1 C1 H10A 110.1 . . ? C2 C1 H10A 110.1 . . ? N1 C1 H10B 110.1 . . ? C2 C1 H10B 110.1 . . ? H10A C1 H10B 108.5 . . ? O1' C2' C1' 109.5(5) . . ? O1' C2' H14A 109.8 . . ? C1' C2' H14A 109.8 . . ? O1' C2' H14B 109.8 . . ? C1' C2' H14B 109.8 . . ? H14A C2' H14B 108.2 . . ? C4 O2 V1 116.4(3) . . ? O2 C4 C3 108.7(5) . . ? O2 C4 H21A 110.0 . . ? C3 C4 H21A 110.0 . . ? O2 C4 H21B 110.0 . . ? C3 C4 H21B 110.0 . . ? H21A C4 H21B 108.3 . . ? O1 C2 C1 109.0(5) . . ? O1 C2 H22A 109.9 . . ? C1 C2 H22A 109.9 . . ? O1 C2 H22B 109.9 . . ? C1 C2 H22B 109.9 . . ? H22A C2 H22B 108.3 . . ? O5 C9 H30A 109.5 . . ? O5 C9 H30B 109.5 . . ? H30A C9 H30B 109.5 . . ? O5 C9 H30C 109.5 . . ? H30A C9 H30C 109.5 . . ? H30B C9 H30C 109.5 . . ? O5' C9' H31A 109.5 . . ? O5' C9' H31B 109.5 . . ? H31A C9' H31B 109.5 . . ? O5' C9' H31C 109.5 . . ? H31A C9' H31C 109.5 . . ? H31B C9' H31C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 66.11 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 1.173 _refine_diff_density_min -0.981 _refine_diff_density_rms 0.168 _database_code_depnum_ccdc_archive 'CCDC 928113'