Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Dr Philip Lightfoot' _publ_contact_author_address ; School of Chemistry University of St Andrews St Andrews Fife KY16 9ST UNITED KINGDOM ; _publ_contact_author_email PL@ST-ANDREWS.AC.UK _publ_section_title ; Hydrothermal chemistry of oligomeric vanadium oxyfluorides ; loop_ _publ_author_name 'Philip Lightfoot' 'David W. Aldous' 'Nicholas F. Stephens' data_I _database_code_depnum_ccdc_archive 'CCDC 634285' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H16 N3, F5 O V, H2 O' _chemical_formula_sum 'C4 H18 F5 N3 O2 V' _chemical_formula_weight 286.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source V V 0.3005 0.5294 '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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.6994(10) _cell_length_b 12.5576(13) _cell_length_c 9.8201(11) _cell_angle_alpha 90.00 _cell_angle_beta 100.011(3) _cell_angle_gamma 90.00 _cell_volume 1056.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 3381 _cell_measurement_theta_min 2.3772 _cell_measurement_theta_max 28.4842 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.0400 _exptl_crystal_size_mid 0.0400 _exptl_crystal_size_min 0.0400 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.799 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 588 _exptl_absorpt_coefficient_mu 0.999 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8688 _exptl_absorpt_correction_T_max 0.9600 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Rotating ANODE' _diffrn_radiation_monochromator 'confocal optics' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6760 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1851 _reflns_number_gt 1656 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004' _computing_structure_solution 'SHELXS-97 (Shledrick 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^)+(0.0368P)^2^+0.1999P] 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 1851 _refine_ls_number_parameters 142 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0884 _refine_ls_wR_factor_gt 0.0741 _refine_ls_goodness_of_fit_ref 1.291 _refine_ls_restrained_S_all 1.291 _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 0.28950(5) 0.91765(3) 0.23869(4) 0.00990(16) Uani 1 1 d . . . F1 F 0.45223(18) 0.81306(11) 0.29465(15) 0.0200(4) Uani 1 1 d . . . F2 F 0.14222(17) 0.80183(11) 0.18911(15) 0.0174(4) Uani 1 1 d . . . F3 F 0.45513(16) 1.02088(11) 0.23686(15) 0.0164(4) Uani 1 1 d . . . F4 F 0.14705(16) 1.01360(11) 0.12729(15) 0.0165(4) Uani 1 1 d . . . F5 F 0.35226(16) 0.88488(11) 0.04343(13) 0.0121(3) Uani 1 1 d . . . O1 O 0.2500(2) 0.94338(14) 0.39028(18) 0.0172(4) Uani 1 1 d . . . N1 N 0.1150(2) 0.88734(15) -0.1703(2) 0.0117(5) Uani 1 1 d . . . H1A H 0.1086 0.8226 -0.2077 0.018 Uiso 1 1 calc R . . H1B H 0.0205 0.9084 -0.1585 0.018 Uiso 1 1 calc R . . H1C H 0.1785 0.8857 -0.0889 0.018 Uiso 1 1 calc R . . N2 N 0.3235(2) 1.08610(15) -0.0849(2) 0.0097(5) Uani 1 1 d . . . H2A H 0.4155 1.0868 -0.1150 0.012 Uiso 1 1 calc R . . H2B H 0.3230 1.0292 -0.0294 0.012 Uiso 1 1 calc R . . N3 N 0.4858(2) 1.31797(15) -0.0855(2) 0.0119(5) Uani 1 1 d . . . H3A H 0.4871 1.3781 -0.1333 0.018 Uiso 1 1 calc R . . H3B H 0.5313 1.2664 -0.1262 0.018 Uiso 1 1 calc R . . H3C H 0.5373 1.3275 0.0002 0.018 Uiso 1 1 calc R . . C1 C 0.1775(3) 0.9634(2) -0.2641(3) 0.0175(6) Uani 1 1 d . . . H1D H 0.1081 0.9646 -0.3528 0.021 Uiso 1 1 calc R . . H1E H 0.2787 0.9385 -0.2794 0.021 Uiso 1 1 calc R . . C2 C 0.1942(3) 1.07503(19) -0.2065(3) 0.0152(6) Uani 1 1 d . . . H2C H 0.2134 1.1233 -0.2788 0.018 Uiso 1 1 calc R . . H2D H 0.0967 1.0960 -0.1790 0.018 Uiso 1 1 calc R . . C3 C 0.3095(3) 1.18558(19) -0.0031(3) 0.0143(6) Uani 1 1 d . . . H3D H 0.3908 1.1850 0.0782 0.017 Uiso 1 1 calc R . . H3E H 0.2098 1.1844 0.0284 0.017 Uiso 1 1 calc R . . C4 C 0.3214(3) 1.28769(19) -0.0808(3) 0.0135(6) Uani 1 1 d . . . H4A H 0.2649 1.2799 -0.1745 0.016 Uiso 1 1 calc R . . H4B H 0.2722 1.3445 -0.0369 0.016 Uiso 1 1 calc R . . O2 O 0.0058(2) 0.69333(16) -0.0345(2) 0.0204(5) Uani 1 1 d . . . H1 H 0.059(3) 0.723(2) 0.037(3) 0.024 Uiso 1 1 d . . . H2 H 0.066(4) 0.662(3) -0.058(3) 0.024 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 0.0109(3) 0.0095(2) 0.0094(2) -0.00011(16) 0.00221(18) 0.00092(18) F1 0.0245(9) 0.0202(8) 0.0135(8) -0.0020(6) -0.0015(6) 0.0140(7) F2 0.0214(9) 0.0129(7) 0.0183(8) 0.0004(6) 0.0040(6) -0.0070(7) F3 0.0133(8) 0.0169(8) 0.0198(8) -0.0062(6) 0.0048(6) -0.0052(7) F4 0.0126(8) 0.0177(8) 0.0198(8) 0.0057(6) 0.0043(6) 0.0041(7) F5 0.0131(8) 0.0129(7) 0.0103(7) 0.0002(6) 0.0023(6) 0.0004(6) O1 0.0223(11) 0.0167(9) 0.0141(9) -0.0002(8) 0.0070(8) -0.0018(8) N1 0.0096(11) 0.0097(10) 0.0149(11) -0.0033(9) 0.0001(9) 0.0003(9) N2 0.0081(11) 0.0098(11) 0.0115(11) 0.0021(8) 0.0028(8) -0.0024(9) N3 0.0144(12) 0.0094(10) 0.0123(11) 0.0025(8) 0.0031(9) -0.0019(9) C1 0.0144(14) 0.0250(15) 0.0135(13) -0.0007(11) 0.0037(11) -0.0047(12) C2 0.0152(15) 0.0128(13) 0.0158(13) 0.0018(11) -0.0022(11) -0.0006(12) C3 0.0165(15) 0.0150(13) 0.0124(13) -0.0029(10) 0.0052(11) -0.0007(12) C4 0.0129(14) 0.0128(13) 0.0154(13) 0.0012(10) 0.0038(11) 0.0003(11) O2 0.0162(12) 0.0252(12) 0.0198(11) -0.0036(9) 0.0029(9) 0.0013(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 1.6174(18) . ? V1 F4 1.9269(14) . ? V1 F1 1.9392(14) . ? V1 F3 1.9407(14) . ? V1 F2 1.9435(14) . ? V1 F5 2.1233(14) . ? N1 C1 1.494(3) . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? N2 C2 1.498(3) . ? N2 C3 1.502(3) . ? N2 H2A 0.9000 . ? N2 H2B 0.9000 . ? N3 C4 1.489(3) . ? N3 H3A 0.8900 . ? N3 H3B 0.8900 . ? N3 H3C 0.8900 . ? C1 C2 1.509(3) . ? C1 H1D 0.9700 . ? C1 H1E 0.9700 . ? C2 H2C 0.9700 . ? C2 H2D 0.9700 . ? C3 C4 1.505(3) . ? C3 H3D 0.9700 . ? C3 H3E 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? O2 H1 0.85(3) . ? O2 H2 0.73(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 F4 100.32(8) . . ? O1 V1 F1 97.80(8) . . ? F4 V1 F1 161.83(6) . . ? O1 V1 F3 98.73(8) . . ? F4 V1 F3 88.99(6) . . ? F1 V1 F3 87.04(7) . . ? O1 V1 F2 98.28(8) . . ? F4 V1 F2 89.70(6) . . ? F1 V1 F2 88.92(7) . . ? F3 V1 F2 162.90(6) . . ? O1 V1 F5 177.39(8) . . ? F4 V1 F5 81.34(6) . . ? F1 V1 F5 80.50(6) . . ? F3 V1 F5 79.23(6) . . ? F2 V1 F5 83.71(6) . . ? C1 N1 H1A 109.5 . . ? C1 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? C2 N2 C3 112.57(19) . . ? C2 N2 H2A 109.1 . . ? C3 N2 H2A 109.1 . . ? C2 N2 H2B 109.1 . . ? C3 N2 H2B 109.1 . . ? H2A N2 H2B 107.8 . . ? C4 N3 H3A 109.5 . . ? C4 N3 H3B 109.5 . . ? H3A N3 H3B 109.5 . . ? C4 N3 H3C 109.5 . . ? H3A N3 H3C 109.5 . . ? H3B N3 H3C 109.5 . . ? N1 C1 C2 112.6(2) . . ? N1 C1 H1D 109.1 . . ? C2 C1 H1D 109.1 . . ? N1 C1 H1E 109.1 . . ? C2 C1 H1E 109.1 . . ? H1D C1 H1E 107.8 . . ? N2 C2 C1 113.3(2) . . ? N2 C2 H2C 108.9 . . ? C1 C2 H2C 108.9 . . ? N2 C2 H2D 108.9 . . ? C1 C2 H2D 108.9 . . ? H2C C2 H2D 107.7 . . ? N2 C3 C4 114.7(2) . . ? N2 C3 H3D 108.6 . . ? C4 C3 H3D 108.6 . . ? N2 C3 H3E 108.6 . . ? C4 C3 H3E 108.6 . . ? H3D C3 H3E 107.6 . . ? N3 C4 C3 112.6(2) . . ? N3 C4 H4A 109.1 . . ? C3 C4 H4A 109.1 . . ? N3 C4 H4B 109.1 . . ? C3 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? H1 O2 H2 100(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1C F5 0.89 1.81 2.676(2) 162.2 . N2 H2B F5 0.90 1.95 2.815(2) 161.0 . N2 H2B F4 0.90 2.35 2.939(2) 122.5 . O2 H1 F2 0.86(3) 1.83(3) 2.680(2) 170(3) . N1 H1A F2 0.89 1.91 2.778(3) 163.6 4_575 O2 H2 O1 0.72(4) 2.20(4) 2.922(3) 175(4) 4_575 N1 H1B F4 0.89 1.83 2.694(2) 164.8 3_575 N2 H2A F5 0.90 2.06 2.803(2) 140.2 3_675 N2 H2A F3 0.90 2.24 2.956(2) 137.1 3_675 N3 H3A F3 0.89 1.78 2.655(2) 164.4 4_585 N3 H3C F1 0.89 2.01 2.816(3) 149.5 2_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.399 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.084 #===end data_2 _database_code_depnum_ccdc_archive 'CCDC 634286' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H22 N4, 2(F5 H2 O V)' _chemical_formula_sum 'C6 H26 F10 N4 O2 V2' _chemical_formula_weight 478.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source V V 0.3005 0.5294 '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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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' H H 0.0000 0.0000 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.660(2) _cell_length_b 9.160(2) _cell_length_c 11.640(3) _cell_angle_alpha 109.460(8) _cell_angle_beta 93.610(3) _cell_angle_gamma 91.860(8) _cell_volume 867.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 4503 _cell_measurement_theta_min 1.8614 _cell_measurement_theta_max 28.6986 _exptl_crystal_description Prism _exptl_crystal_colour Blue _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.100 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.831 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 1.186 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.805 _exptl_absorpt_correction_T_max 0.887 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Confocal optics' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5930 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 26.33 _reflns_number_total 3391 _reflns_number_gt 2826 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Crystalclear (Rigaku Corp., 2004)' _computing_cell_refinement 'Crystalclear (Rigaku Corp., 2004)' _computing_data_reduction 'Crystalclear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1760P)^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 3391 _refine_ls_number_parameters 233 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.2400 _refine_ls_wR_factor_gt 0.1485 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.123 _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 0.11950(7) 0.47767(6) 0.70694(5) 0.0061(3) Uani 1 1 d . . . V2 V 0.53347(7) 0.92143(6) 0.76922(5) 0.0061(3) Uani 1 1 d . . . F1 F -0.0028(2) 0.4010(2) 0.81441(19) 0.0086(5) Uani 1 1 d . . . F2 F 0.2814(3) 0.5599(3) 0.8220(2) 0.0145(5) Uani 1 1 d . . . F3 F 0.0067(2) 0.6613(2) 0.7553(2) 0.0107(5) Uani 1 1 d . . . F4 F -0.0420(2) 0.3869(2) 0.57431(19) 0.0093(5) Uani 1 1 d . . . F5 F 0.2073(2) 0.2775(2) 0.6479(2) 0.0099(5) Uani 1 1 d . . . F6 F 0.6505(2) 0.9866(2) 0.6524(2) 0.0090(5) Uani 1 1 d . . . F7 F 0.6802(3) 1.0177(2) 0.9008(2) 0.0136(5) Uani 1 1 d . . . F8 F 0.6420(3) 0.7346(2) 0.7264(2) 0.0116(5) Uani 1 1 d . . . F9 F 0.3832(2) 0.8177(2) 0.63244(19) 0.0107(5) Uani 1 1 d . . . F10 F 0.4249(2) 1.1075(2) 0.8020(2) 0.0122(5) Uani 1 1 d . . . O1 O 0.2322(3) 0.5483(3) 0.5808(3) 0.0097(6) Uani 1 1 d . . . O2 O 0.3989(4) 0.8445(4) 0.8800(3) 0.0212(8) Uani 1 1 d . . . N1 N 0.5020(3) 0.2149(3) 0.5949(3) 0.0079(6) Uani 1 1 d . . . H1A H 0.5010 0.1868 0.5139 0.012 Uiso 1 1 calc R . . H1B H 0.4067 0.2362 0.6175 0.012 Uiso 1 1 calc R . . H1C H 0.5346 0.1379 0.6190 0.012 Uiso 1 1 calc R . . C1 C 0.6083(4) 0.3552(4) 0.6520(3) 0.0090(7) Uani 1 1 d . . . H1D H 0.5736 0.4385 0.6245 0.011 Uiso 1 1 calc R . . H1E H 0.7117 0.3323 0.6260 0.011 Uiso 1 1 calc R . . C2 C 0.6139(4) 0.4076(4) 0.7905(3) 0.0074(7) Uani 1 1 d . . . H2A H 0.5124 0.4371 0.8181 0.009 Uiso 1 1 calc R . . H2B H 0.6455 0.3243 0.8192 0.009 Uiso 1 1 calc R . . N2 N 0.7276(3) 0.5422(3) 0.8384(3) 0.0067(6) Uani 1 1 d . . . H2C H 0.7063 0.6102 0.7996 0.008 Uiso 1 1 calc R . . H2D H 0.8228 0.5094 0.8206 0.008 Uiso 1 1 calc R . . C3 C 0.7294(4) 0.6238(4) 0.9721(3) 0.0092(7) Uani 1 1 d . . . H3A H 0.7560 0.5532 1.0155 0.011 Uiso 1 1 calc R . . H3B H 0.6275 0.6601 0.9930 0.011 Uiso 1 1 calc R . . C4 C 0.8484(4) 0.7612(4) 1.0093(3) 0.0085(7) Uani 1 1 d . . . H4A H 0.9483 0.7265 0.9812 0.010 Uiso 1 1 calc R . . H4B H 0.8163 0.8373 0.9727 0.010 Uiso 1 1 calc R . . N3 N 0.8605(3) 0.8315(3) 1.1449(3) 0.0059(6) Uani 1 1 d . . . H3C H 0.7654 0.8557 1.1698 0.007 Uiso 1 1 calc R . . H3D H 0.8943 0.7607 1.1773 0.007 Uiso 1 1 calc R . . C5 C 0.9660(4) 0.9730(4) 1.1926(3) 0.0080(7) Uani 1 1 d . . . H5A H 0.9305 1.0510 1.1592 0.010 Uiso 1 1 calc R . . H5B H 1.0697 0.9484 1.1682 0.010 Uiso 1 1 calc R . . C6 C 0.9683(4) 1.0350(4) 1.3312(3) 0.0075(7) Uani 1 1 d . . . H6A H 0.8666 1.0684 1.3555 0.009 Uiso 1 1 calc R . . H6B H 0.9946 0.9539 1.3641 0.009 Uiso 1 1 calc R . . N4 N 1.0846(3) 1.1678(3) 1.3799(3) 0.0072(6) Uani 1 1 d . . . H4C H 1.0864 1.2044 1.4611 0.011 Uiso 1 1 calc R . . H4D H 1.0594 1.2423 1.3500 0.011 Uiso 1 1 calc R . . H4E H 1.1778 1.1364 1.3578 0.011 Uiso 1 1 calc R . . H11 H 0.283(6) 0.624(6) 0.598(5) 0.033(16) Uiso 1 1 d . . . H21 H 0.171(6) 0.553(5) 0.527(5) 0.016(12) Uiso 1 1 d . . . H12 H 0.362(5) 0.767(5) 0.857(4) 0.000(10) Uiso 1 1 d . . . H22 H 0.386(5) 0.890(5) 0.947(5) 0.010(11) 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 0.0063(4) 0.0050(4) 0.0078(4) 0.0027(3) 0.0019(3) 0.0023(3) V2 0.0062(4) 0.0062(4) 0.0060(4) 0.0022(3) 0.0003(3) 0.0018(3) F1 0.0079(11) 0.0091(11) 0.0122(12) 0.0072(8) 0.0031(9) 0.0040(8) F2 0.0139(12) 0.0144(12) 0.0158(12) 0.0069(9) -0.0044(9) -0.0005(8) F3 0.0116(12) 0.0102(11) 0.0117(12) 0.0044(8) 0.0038(9) 0.0050(8) F4 0.0062(11) 0.0137(12) 0.0072(11) 0.0033(8) -0.0031(8) -0.0015(8) F5 0.0088(11) 0.0079(11) 0.0142(12) 0.0047(8) 0.0030(9) 0.0026(7) F6 0.0076(11) 0.0102(11) 0.0118(12) 0.0065(8) 0.0031(9) 0.0039(8) F7 0.0143(12) 0.0165(12) 0.0082(12) 0.0022(8) -0.0010(9) 0.0011(8) F8 0.0164(12) 0.0093(11) 0.0116(12) 0.0063(8) 0.0025(9) 0.0046(8) F9 0.0093(11) 0.0127(11) 0.0076(11) 0.0015(8) -0.0037(9) -0.0041(8) F10 0.0068(11) 0.0110(11) 0.0175(12) 0.0027(8) 0.0022(9) 0.0017(8) O1 0.0075(14) 0.0135(15) 0.0105(15) 0.0074(11) -0.0013(11) -0.0009(10) O2 0.0338(19) 0.0113(17) 0.0135(17) -0.0035(12) 0.0142(14) -0.0128(13) N1 0.0082(15) 0.0077(15) 0.0084(15) 0.0036(11) 0.0004(12) 0.0033(10) C1 0.0103(18) 0.0075(17) 0.0087(18) 0.0025(13) -0.0006(14) -0.0002(12) C2 0.0066(17) 0.0066(17) 0.0089(18) 0.0027(12) -0.0001(14) -0.0006(12) N2 0.0054(15) 0.0057(14) 0.0090(15) 0.0022(11) -0.0001(11) 0.0021(10) C3 0.0100(18) 0.0118(18) 0.0062(18) 0.0038(12) 0.0003(14) 0.0007(12) C4 0.0099(18) 0.0103(17) 0.0059(17) 0.0036(12) 0.0010(14) 0.0011(13) N3 0.0063(15) 0.0057(14) 0.0055(15) 0.0014(10) 0.0005(11) 0.0023(10) C5 0.0081(17) 0.0071(17) 0.0088(18) 0.0028(12) 0.0003(14) -0.0018(12) C6 0.0064(17) 0.0063(17) 0.0082(18) 0.0013(12) -0.0028(13) -0.0040(12) N4 0.0074(15) 0.0081(15) 0.0050(15) 0.0007(11) -0.0014(12) 0.0028(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 F2 1.831(2) . ? V1 F3 1.909(2) . ? V1 F5 1.931(2) . ? V1 F4 1.956(2) . ? V1 F1 1.970(2) . ? V1 O1 2.073(3) . ? V2 F7 1.876(2) . ? V2 F10 1.911(2) . ? V2 F8 1.912(2) . ? V2 F9 1.945(2) . ? V2 F6 1.976(2) . ? V2 O2 2.063(3) . ? O1 H11 0.77(6) . ? O1 H21 0.81(5) . ? O2 H12 0.73(4) . ? O2 H22 0.78(5) . ? N1 C1 1.490(4) . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? C1 C2 1.518(5) . ? C1 H1D 0.9700 . ? C1 H1E 0.9700 . ? C2 N2 1.481(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? N2 C3 1.484(4) . ? N2 H2C 0.9000 . ? N2 H2D 0.9000 . ? C3 C4 1.526(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N3 1.488(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? N3 C5 1.484(4) . ? N3 H3C 0.9000 . ? N3 H3D 0.9000 . ? C5 C6 1.519(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N4 1.485(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? N4 H4C 0.8900 . ? N4 H4D 0.8900 . ? N4 H4E 0.8900 . ? 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 F2 V1 F3 94.27(10) . . ? F2 V1 F5 92.99(9) . . ? F3 V1 F5 172.27(9) . . ? F2 V1 F4 175.57(9) . . ? F3 V1 F4 88.10(9) . . ? F5 V1 F4 84.84(9) . . ? F2 V1 F1 94.79(10) . . ? F3 V1 F1 87.88(9) . . ? F5 V1 F1 88.88(9) . . ? F4 V1 F1 89.04(9) . . ? F2 V1 O1 90.57(11) . . ? F3 V1 O1 92.15(10) . . ? F5 V1 O1 90.42(10) . . ? F4 V1 O1 85.59(11) . . ? F1 V1 O1 174.62(11) . . ? F7 V2 F10 91.16(10) . . ? F7 V2 F8 91.06(10) . . ? F10 V2 F8 176.55(9) . . ? F7 V2 F9 178.85(8) . . ? F10 V2 F9 89.98(9) . . ? F8 V2 F9 87.82(9) . . ? F7 V2 F6 93.33(10) . . ? F10 V2 F6 88.48(9) . . ? F8 V2 F6 88.75(9) . . ? F9 V2 F6 86.85(9) . . ? F7 V2 O2 91.12(12) . . ? F10 V2 O2 91.58(12) . . ? F8 V2 O2 91.02(12) . . ? F9 V2 O2 88.69(12) . . ? F6 V2 O2 175.54(11) . . ? V1 O1 H11 123(4) . . ? V1 O1 H21 111(3) . . ? H11 O1 H21 104(5) . . ? V2 O2 H12 120(3) . . ? V2 O2 H22 126(3) . . ? H12 O2 H22 114(4) . . ? C1 N1 H1A 109.5 . . ? C1 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? N1 C1 C2 111.4(3) . . ? N1 C1 H1D 109.3 . . ? C2 C1 H1D 109.3 . . ? N1 C1 H1E 109.3 . . ? C2 C1 H1E 109.3 . . ? H1D C1 H1E 108.0 . . ? N2 C2 C1 107.3(3) . . ? N2 C2 H2A 110.3 . . ? C1 C2 H2A 110.3 . . ? N2 C2 H2B 110.3 . . ? C1 C2 H2B 110.3 . . ? H2A C2 H2B 108.5 . . ? C2 N2 C3 114.3(3) . . ? C2 N2 H2C 108.7 . . ? C3 N2 H2C 108.7 . . ? C2 N2 H2D 108.7 . . ? C3 N2 H2D 108.7 . . ? H2C N2 H2D 107.6 . . ? N2 C3 C4 109.2(3) . . ? N2 C3 H3A 109.8 . . ? C4 C3 H3A 109.8 . . ? N2 C3 H3B 109.8 . . ? C4 C3 H3B 109.8 . . ? H3A C3 H3B 108.3 . . ? N3 C4 C3 108.4(3) . . ? N3 C4 H4A 110.0 . . ? C3 C4 H4A 110.0 . . ? N3 C4 H4B 110.0 . . ? C3 C4 H4B 110.0 . . ? H4A C4 H4B 108.4 . . ? C5 N3 C4 113.7(3) . . ? C5 N3 H3C 108.8 . . ? C4 N3 H3C 108.8 . . ? C5 N3 H3D 108.8 . . ? C4 N3 H3D 108.8 . . ? H3C N3 H3D 107.7 . . ? N3 C5 C6 109.1(3) . . ? N3 C5 H5A 109.9 . . ? C6 C5 H5A 109.9 . . ? N3 C5 H5B 109.9 . . ? C6 C5 H5B 109.9 . . ? H5A C5 H5B 108.3 . . ? N4 C6 C5 109.2(3) . . ? N4 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? N4 C6 H6B 109.8 . . ? C5 C6 H6B 109.8 . . ? H6A C6 H6B 108.3 . . ? C6 N4 H4C 109.5 . . ? C6 N4 H4D 109.5 . . ? H4C N4 H4D 109.5 . . ? C6 N4 H4E 109.5 . . ? H4C N4 H4E 109.5 . . ? H4D N4 H4E 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1B F5 0.89 1.81 2.698(4) 174.2 . N2 H2C F8 0.90 1.72 2.617(3) 172.9 . O1 H11 F9 0.77(6) 1.86(6) 2.620(3) 172(6) . O2 H12 F2 0.73(4) 1.90(4) 2.618(4) 170(4) . N1 H1A F9 0.89 2.02 2.811(4) 147.5 2_666 N1 H1C F6 0.89 1.86 2.734(3) 165.0 1_545 N1 H1C F10 0.89 2.48 2.994(4) 117.3 1_545 N2 H2D F1 0.90 1.83 2.691(4) 160.4 1_655 N2 H2D F3 0.90 2.40 2.966(4) 120.9 1_655 N3 H3C F10 0.90 1.72 2.618(4) 172.7 2_677 O2 H22 F7 0.78(5) 1.82(5) 2.589(4) 170(5) 2_677 N4 H4D F3 0.89 1.81 2.668(3) 161.1 2_677 N3 H3D F1 0.90 1.81 2.655(3) 156.4 2_667 N3 H3D F5 0.90 2.39 2.984(3) 123.5 2_667 N4 H4C F4 0.89 2.15 2.789(4) 128.6 1_666 N4 H4E F6 0.89 1.88 2.715(4) 155.3 2_777 N4 H4E F8 0.89 2.37 2.984(4) 125.8 2_777 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 26.33 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 2.064 _refine_diff_density_min -1.829 _refine_diff_density_rms 0.517 #===end data_3 _database_code_depnum_ccdc_archive 'CCDC 634287' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H22 N4, 2(F4 H2 O2 V), H2 O' _chemical_formula_sum 'C6 H28 F8 N4 O5 V2' _chemical_formula_weight 490.20 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' F F 0.0171 0.0103 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.884(4) _cell_length_b 9.143(4) _cell_length_c 11.951(5) _cell_angle_alpha 103.008(6) _cell_angle_beta 108.336(8) _cell_angle_gamma 92.849(7) _cell_volume 890.2(7) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 4523 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.100 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.829 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 1.155 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.891 _exptl_absorpt_correction_T_max 0.891 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Confocal Optics' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6087 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0634 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 28.14 _reflns_number_total 4362 _reflns_number_gt 2793 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _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.In this structure solution, six distance restraints have been used. These were all of 0.85 Angstroms and were used to restrain six hydrogen atoms attached to three differnt oxygen atoms, all in water molecules. ; _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^)+(0.1845P)^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 SHELXL _refine_ls_extinction_coef 0.051(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4362 _refine_ls_number_parameters 249 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0787 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.2354 _refine_ls_wR_factor_gt 0.1420 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.050 _refine_ls_shift/su_mean 0.051 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 0.21138(8) 0.73048(8) 0.40630(6) 0.0069(3) Uani 1 1 d . . . V2 V -0.22237(8) 0.25260(8) 0.07133(6) 0.0075(3) Uani 1 1 d . . . F1 F 0.4265(3) 0.8078(3) 0.4253(2) 0.0110(6) Uani 1 1 d . . . F2 F 0.1390(3) 0.8517(3) 0.2906(2) 0.0111(6) Uani 1 1 d . . . F3 F -0.0007(3) 0.6144(3) 0.3560(2) 0.0123(6) Uani 1 1 d . . . F4 F 0.2911(3) 0.5630(3) 0.4701(2) 0.0147(6) Uani 1 1 d . . . O1 O 0.1934(3) 0.8431(4) 0.5243(3) 0.0146(7) Uani 1 1 d . . . O2 O 0.2274(3) 0.5681(3) 0.2335(3) 0.0103(7) Uani 1 1 d D . . H1 H 0.141(4) 0.504(5) 0.203(4) 0.015 Uiso 1 1 d D . . H2 H 0.250(5) 0.597(6) 0.176(3) 0.015 Uiso 1 1 d D . . O3 O -0.2759(4) 0.3302(4) -0.0441(3) 0.0142(7) Uani 1 1 d . . . O4 O -0.2441(3) 0.4330(4) 0.1980(3) 0.0120(7) Uani 1 1 d D . . H3 H -0.159(4) 0.488(5) 0.249(4) 0.015(13) Uiso 1 1 d D . . H4 H -0.324(7) 0.437(10) 0.222(8) 0.08(3) Uiso 1 1 d D . . O5 O -0.4555(3) 0.4741(4) 0.3119(3) 0.0184(8) Uani 1 1 d D . . H5 H -0.375(5) 0.474(9) 0.372(5) 0.06(2) Uiso 1 1 d D . . H6 H -0.538(4) 0.515(6) 0.292(5) 0.031(16) Uiso 1 1 d D . . F5 F -0.1456(3) 0.1506(3) 0.2153(2) 0.0111(6) Uani 1 1 d . . . F6 F 0.0050(3) 0.3309(3) 0.1264(2) 0.0116(6) Uani 1 1 d . . . F7 F -0.1816(3) 0.0662(3) -0.0162(2) 0.0124(6) Uani 1 1 d . . . F8 F -0.4283(3) 0.1654(3) 0.0585(2) 0.0105(6) Uani 1 1 d . . . N1 N -0.9125(4) 0.1748(4) -0.0671(3) 0.0108(8) Uani 1 1 d . . . H1A H -0.8872 0.0814 -0.0697 0.016 Uiso 1 1 calc R . . H1B H -0.9932 0.1739 -0.1341 0.016 Uiso 1 1 calc R . . H1C H -0.9413 0.2083 -0.0019 0.016 Uiso 1 1 calc R . . N2 N -0.6361(4) 0.0855(4) -0.1670(3) 0.0076(7) Uani 1 1 d . . . H2C H -0.5661 0.0916 -0.0924 0.009 Uiso 1 1 calc R . . H2D H -0.7108 0.0053 -0.1863 0.009 Uiso 1 1 calc R . . N3 N -0.3780(4) -0.0858(4) -0.3458(3) 0.0078(8) Uani 1 1 d . . . H3C H -0.4495 -0.1123 -0.4217 0.009 Uiso 1 1 calc R . . H3D H -0.3255 0.0058 -0.3348 0.009 Uiso 1 1 calc R . . N4 N -0.0676(4) -0.3134(4) -0.4217(3) 0.0094(8) Uani 1 1 d . . . H4C H -0.0260 -0.3212 -0.4812 0.014 Uiso 1 1 calc R . . H4D H -0.1116 -0.4043 -0.4246 0.014 Uiso 1 1 calc R . . H4E H 0.0091 -0.2767 -0.3500 0.014 Uiso 1 1 calc R . . C1 C -0.7720(5) 0.2759(5) -0.0594(4) 0.0110(9) Uani 1 1 d . . . H1D H -0.6857 0.2785 0.0151 0.013 Uiso 1 1 calc R . . H1E H -0.7999 0.3778 -0.0550 0.013 Uiso 1 1 calc R . . C2 C -0.7135(5) 0.2271(5) -0.1665(4) 0.0122(9) Uani 1 1 d . . . H2A H -0.8034 0.2111 -0.2415 0.015 Uiso 1 1 calc R . . H2B H -0.6373 0.3080 -0.1648 0.015 Uiso 1 1 calc R . . C3 C -0.5520(5) 0.0656(5) -0.2571(4) 0.0072(8) Uani 1 1 d . . . H3A H -0.4751 0.1543 -0.2382 0.009 Uiso 1 1 calc R . . H3B H -0.6285 0.0551 -0.3378 0.009 Uiso 1 1 calc R . . C4 C -0.4655(5) -0.0751(5) -0.2557(4) 0.0072(8) Uani 1 1 d . . . H4A H -0.3906 -0.0667 -0.1747 0.009 Uiso 1 1 calc R . . H4B H -0.5421 -0.1650 -0.2780 0.009 Uiso 1 1 calc R . . C5 C -0.2619(5) -0.1976(5) -0.3339(4) 0.0093(9) Uani 1 1 d . . . H5A H -0.3153 -0.2954 -0.3393 0.011 Uiso 1 1 calc R . . H5B H -0.1773 -0.1649 -0.2554 0.011 Uiso 1 1 calc R . . C6 C -0.1910(5) -0.2104(5) -0.4373(4) 0.0095(9) Uani 1 1 d . . . H6A H -0.2748 -0.2494 -0.5156 0.011 Uiso 1 1 calc R . . H6B H -0.1441 -0.1113 -0.4351 0.011 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 0.0095(5) 0.0070(5) 0.0035(5) 0.0026(3) 0.0009(3) -0.0013(3) V2 0.0093(5) 0.0092(5) 0.0038(5) 0.0026(3) 0.0014(3) -0.0002(3) F1 0.0108(12) 0.0138(14) 0.0069(13) 0.0038(10) 0.0008(9) -0.0025(10) F2 0.0128(13) 0.0107(14) 0.0069(13) 0.0044(10) -0.0019(9) -0.0012(10) F3 0.0123(12) 0.0132(14) 0.0102(14) 0.0012(11) 0.0039(10) -0.0037(10) F4 0.0188(13) 0.0119(14) 0.0127(14) 0.0074(11) 0.0013(10) 0.0013(10) O1 0.0157(15) 0.0168(18) 0.0087(16) -0.0018(13) 0.0049(12) -0.0046(13) O2 0.0126(14) 0.0115(16) 0.0079(16) 0.0044(13) 0.0040(11) -0.0021(12) O3 0.0265(16) 0.0097(16) 0.0048(15) 0.0032(12) 0.0028(12) -0.0033(13) O4 0.0086(15) 0.0137(17) 0.0105(16) -0.0021(13) 0.0027(12) -0.0007(13) O5 0.0110(17) 0.034(2) 0.0138(18) 0.0106(16) 0.0044(13) 0.0106(15) F5 0.0109(12) 0.0146(14) 0.0067(13) 0.0071(10) -0.0012(9) -0.0013(10) F6 0.0097(12) 0.0116(14) 0.0120(13) 0.0010(11) 0.0032(10) -0.0012(10) F7 0.0175(13) 0.0095(13) 0.0081(13) -0.0010(10) 0.0042(10) -0.0010(10) F8 0.0108(12) 0.0127(14) 0.0075(13) 0.0034(10) 0.0025(9) -0.0016(10) N1 0.0132(17) 0.0102(19) 0.0096(18) 0.0037(15) 0.0036(14) 0.0027(14) N2 0.0102(17) 0.0077(18) 0.0039(17) 0.0016(14) 0.0007(13) 0.0003(14) N3 0.0105(17) 0.0076(18) 0.0063(17) 0.0030(14) 0.0035(13) -0.0007(14) N4 0.0126(17) 0.0093(18) 0.0055(18) 0.0023(14) 0.0022(13) -0.0011(14) C1 0.013(2) 0.010(2) 0.010(2) 0.0022(17) 0.0049(17) 0.0010(17) C2 0.017(2) 0.011(2) 0.013(2) 0.0073(18) 0.0087(18) 0.0019(17) C3 0.0091(19) 0.007(2) 0.007(2) 0.0048(16) 0.0031(15) 0.0010(16) C4 0.0113(19) 0.007(2) 0.005(2) 0.0028(16) 0.0049(15) 0.0017(16) C5 0.010(2) 0.012(2) 0.007(2) 0.0051(17) 0.0022(15) 0.0060(16) C6 0.011(2) 0.011(2) 0.008(2) 0.0052(17) 0.0034(16) 0.0023(17) _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 1.606(3) . ? V1 F4 1.929(3) . ? V1 F1 1.930(2) . ? V1 F2 1.938(3) . ? V1 F3 1.960(2) . ? V1 O2 2.305(3) . ? V2 O3 1.641(3) . ? V2 F7 1.905(3) . ? V2 F8 1.905(2) . ? V2 F6 1.958(2) . ? V2 O4 2.035(3) . ? V2 F5 2.084(3) . ? O2 H1 0.87(2) . ? O2 H2 0.86(4) . ? O4 H3 0.85(2) . ? O4 H4 0.85(7) . ? O5 H5 0.84(5) . ? O5 H6 0.83(5) . ? N1 C1 1.482(5) . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? N2 C3 1.478(5) . ? N2 C2 1.496(6) . ? N2 H2C 0.9000 . ? N2 H2D 0.9000 . ? N3 C5 1.485(5) . ? N3 C4 1.503(5) . ? N3 H3C 0.9000 . ? N3 H3D 0.9000 . ? N4 C6 1.475(5) . ? N4 H4C 0.8900 . ? N4 H4D 0.8900 . ? N4 H4E 0.8900 . ? C1 C2 1.514(6) . ? C1 H1D 0.9700 . ? C1 H1E 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.531(6) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.540(6) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? 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 F4 101.72(15) . . ? O1 V1 F1 98.59(13) . . ? F4 V1 F1 89.83(11) . . ? O1 V1 F2 98.88(15) . . ? F4 V1 F2 159.39(12) . . ? F1 V1 F2 86.93(10) . . ? O1 V1 F3 94.90(13) . . ? F4 V1 F3 85.63(11) . . ? F1 V1 F3 166.38(11) . . ? F2 V1 F3 92.81(10) . . ? O1 V1 O2 177.94(13) . . ? F4 V1 O2 79.23(11) . . ? F1 V1 O2 83.21(11) . . ? F2 V1 O2 80.18(11) . . ? F3 V1 O2 83.32(10) . . ? O3 V2 F7 96.46(14) . . ? O3 V2 F8 98.80(13) . . ? F7 V2 F8 91.84(10) . . ? O3 V2 F6 95.78(13) . . ? F7 V2 F6 90.12(10) . . ? F8 V2 F6 164.97(11) . . ? O3 V2 O4 96.31(15) . . ? F7 V2 O4 167.11(12) . . ? F8 V2 O4 87.95(11) . . ? F6 V2 O4 86.85(11) . . ? O3 V2 F5 177.33(13) . . ? F7 V2 F5 81.62(11) . . ? F8 V2 F5 83.15(10) . . ? F6 V2 F5 82.40(10) . . ? O4 V2 F5 85.56(12) . . ? V1 O2 H1 107(4) . . ? V1 O2 H2 124(4) . . ? H1 O2 H2 110(5) . . ? V2 O4 H3 118(4) . . ? V2 O4 H4 123(6) . . ? H3 O4 H4 115(7) . . ? H5 O5 H6 142(7) . . ? C1 N1 H1A 109.5 . . ? C1 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? C3 N2 C2 109.3(3) . . ? C3 N2 H2C 109.8 . . ? C2 N2 H2C 109.8 . . ? C3 N2 H2D 109.8 . . ? C2 N2 H2D 109.8 . . ? H2C N2 H2D 108.3 . . ? C5 N3 C4 112.8(3) . . ? C5 N3 H3C 109.0 . . ? C4 N3 H3C 109.0 . . ? C5 N3 H3D 109.0 . . ? C4 N3 H3D 109.0 . . ? H3C N3 H3D 107.8 . . ? C6 N4 H4C 109.5 . . ? C6 N4 H4D 109.5 . . ? H4C N4 H4D 109.5 . . ? C6 N4 H4E 109.5 . . ? H4C N4 H4E 109.5 . . ? H4D N4 H4E 109.5 . . ? N1 C1 C2 113.3(4) . . ? N1 C1 H1D 108.9 . . ? C2 C1 H1D 108.9 . . ? N1 C1 H1E 108.9 . . ? C2 C1 H1E 108.9 . . ? H1D C1 H1E 107.7 . . ? N2 C2 C1 113.3(4) . . ? N2 C2 H2A 108.9 . . ? C1 C2 H2A 108.9 . . ? N2 C2 H2B 108.9 . . ? C1 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? N2 C3 C4 110.4(4) . . ? N2 C3 H3A 109.6 . . ? C4 C3 H3A 109.6 . . ? N2 C3 H3B 109.5 . . ? C4 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? N3 C4 C3 107.8(4) . . ? N3 C4 H4A 110.2 . . ? C3 C4 H4A 110.1 . . ? N3 C4 H4B 110.1 . . ? C3 C4 H4B 110.2 . . ? H4A C4 H4B 108.5 . . ? N3 C5 C6 108.4(3) . . ? N3 C5 H5A 110.0 . . ? C6 C5 H5A 110.0 . . ? N3 C5 H5B 110.0 . . ? C6 C5 H5B 110.0 . . ? H5A C5 H5B 108.4 . . ? N4 C6 C5 109.0(3) . . ? N4 C6 H6A 109.9 . . ? C5 C6 H6A 109.9 . . ? N4 C6 H6B 109.9 . . ? C5 C6 H6B 109.9 . . ? H6A C6 H6B 108.3 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O3 0.86(4) 1.91(2) 2.774(4) 175(5) 2_565 N3 H3D F2 0.90 1.91 2.749(4) 154.4 2_565 N3 H3D F1 0.90 2.29 2.913(4) 126.1 2_565 O5 H6 O2 0.83(5) 2.10(2) 2.914(4) 167(6) 1_455 N1 H1C F6 0.89 1.89 2.758(4) 164.3 1_455 N1 H1C F7 0.89 2.38 2.832(4) 111.6 1_455 N1 H1A F7 0.89 1.89 2.681(4) 147.7 2_455 N2 H2D F5 0.90 1.76 2.659(4) 176.8 2_455 N1 H1B F2 0.89 1.86 2.743(4) 168.6 2_465 N3 H3C F1 0.90 1.77 2.664(4) 170.2 1_444 N4 H4C F3 0.89 1.99 2.844(4) 160.7 1_544 N4 H4C O1 0.89 2.38 2.977(4) 125.1 1_544 N4 H4D F4 0.89 1.95 2.778(4) 153.6 2 O2 H1 F6 0.87(4) 1.81(5) 2.643(4) 166(5) . O4 H3 F3 0.86(4) 1.73(2) 2.580(4) 174(5) . O4 H4 O5 0.85(7) 1.82(7) 2.641(4) 165(8) . N2 H2C F8 0.90 1.79 2.657(4) 162.0 . _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 28.14 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 2.077 _refine_diff_density_min -2.178 _refine_diff_density_rms 0.503 #===end data_4 _database_code_depnum_ccdc_archive 'CCDC 634288' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H16 N3, F6 V' _chemical_formula_sum 'C4 H16 F6 N3 V' _chemical_formula_weight 271.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.6285(14) _cell_length_b 10.6742(18) _cell_length_c 10.7766(14) _cell_angle_alpha 90.00 _cell_angle_beta 96.651(5) _cell_angle_gamma 90.00 _cell_volume 985.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Chip _exptl_crystal_colour Green _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.827 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 1.065 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.653 _exptl_absorpt_correction_T_max 0.660 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Confocal Optics' _diffrn_measurement_device_type 'CCD Area Detector' _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9622 _diffrn_reflns_av_R_equivalents 0.0700 _diffrn_reflns_av_sigmaI/netI 0.0497 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.11 _reflns_number_total 2173 _reflns_number_gt 2088 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 9Sheldrick, 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^)+(0.0433P)^2^+0.9141P] 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 2173 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0363 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_ref 0.1026 _refine_ls_wR_factor_gt 0.1015 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _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 0.71461(4) 0.06103(3) 0.26590(3) 0.01093(14) Uani 1 1 d . . . F1 F 0.55832(13) -0.02195(11) 0.13802(11) 0.0158(3) Uani 1 1 d . . . F2 F 0.59733(15) 0.02967(13) 0.40125(12) 0.0210(3) Uani 1 1 d . . . F3 F 0.82527(13) -0.09808(11) 0.27672(11) 0.0156(3) Uani 1 1 d . . . F4 F 0.83095(14) 0.10781(11) 0.12279(10) 0.0157(3) Uani 1 1 d . . . F5 F 0.60315(14) 0.22063(11) 0.23361(11) 0.0185(3) Uani 1 1 d . . . F6 F 0.88256(14) 0.13766(12) 0.38037(11) 0.0183(3) Uani 1 1 d . . . N1 N 0.45680(19) 0.25203(16) -0.00426(16) 0.0160(4) Uani 1 1 d . . . H1A H 0.4817 0.3017 -0.0652 0.024 Uiso 1 1 calc R . . H1B H 0.4902 0.1746 -0.0165 0.024 Uiso 1 1 calc R . . H1C H 0.5016 0.2805 0.0689 0.024 Uiso 1 1 calc R . . C1 C 0.2813(2) 0.25080(18) -0.00407(19) 0.0144(4) Uani 1 1 d . . . H1D H 0.2335 0.2219 -0.0849 0.017 Uiso 1 1 calc R . . H1E H 0.2457 0.3358 0.0074 0.017 Uiso 1 1 calc R . . C2 C 0.2262(2) 0.16710(18) 0.09814(19) 0.0148(4) Uani 1 1 d . . . H2A H 0.2769 0.1944 0.1786 0.018 Uiso 1 1 calc R . . H2B H 0.1148 0.1783 0.0986 0.018 Uiso 1 1 calc R . . N2 N 0.25930(19) 0.02949(15) 0.08243(15) 0.0114(3) Uani 1 1 d . . . H2C H 0.3619 0.0158 0.1034 0.014 Uiso 1 1 calc R . . H2D H 0.2363 0.0090 0.0014 0.014 Uiso 1 1 calc R . . C3 C 0.1681(2) -0.05547(17) 0.16052(18) 0.0124(4) Uani 1 1 d . . . H3A H 0.1914 -0.1421 0.1429 0.015 Uiso 1 1 calc R . . H3B H 0.0573 -0.0424 0.1372 0.015 Uiso 1 1 calc R . . C4 C 0.2076(2) -0.03071(19) 0.30136(18) 0.0139(4) Uani 1 1 d . . . H4A H 0.3194 -0.0360 0.3246 0.017 Uiso 1 1 calc R . . H4B H 0.1730 0.0524 0.3220 0.017 Uiso 1 1 calc R . . N3 N 0.12508(19) -0.12847(16) 0.37034(15) 0.0130(3) Uani 1 1 d . . . H3C H 0.1459 -0.1160 0.4522 0.019 Uiso 1 1 calc R . . H3D H 0.1580 -0.2043 0.3511 0.019 Uiso 1 1 calc R . . H3E H 0.0227 -0.1228 0.3484 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 0.0111(2) 0.0104(2) 0.0111(2) -0.00040(11) 0.00038(13) 0.00189(11) F1 0.0125(6) 0.0167(6) 0.0175(6) -0.0030(5) -0.0009(4) -0.0005(5) F2 0.0227(7) 0.0220(6) 0.0199(6) 0.0021(5) 0.0089(5) 0.0008(5) F3 0.0142(6) 0.0131(6) 0.0193(6) 0.0022(5) 0.0011(5) 0.0024(4) F4 0.0186(6) 0.0169(6) 0.0121(6) -0.0005(4) 0.0034(4) -0.0044(5) F5 0.0199(6) 0.0132(6) 0.0213(6) -0.0002(5) -0.0025(5) 0.0042(5) F6 0.0186(6) 0.0204(6) 0.0152(6) -0.0016(5) -0.0009(5) -0.0032(5) N1 0.0171(9) 0.0151(8) 0.0162(8) 0.0010(6) 0.0036(7) -0.0009(7) C1 0.0148(10) 0.0126(9) 0.0156(9) 0.0005(7) 0.0009(7) 0.0007(7) C2 0.0147(9) 0.0107(9) 0.0196(10) -0.0013(7) 0.0051(7) 0.0009(7) N2 0.0109(8) 0.0109(8) 0.0126(8) 0.0003(6) 0.0016(6) 0.0013(6) C3 0.0123(9) 0.0134(9) 0.0115(9) 0.0001(7) 0.0010(7) -0.0019(7) C4 0.0156(10) 0.0137(9) 0.0122(9) -0.0007(7) 0.0011(7) -0.0022(7) N3 0.0129(8) 0.0137(8) 0.0121(8) 0.0003(6) 0.0010(6) -0.0001(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 F2 1.8989(13) . ? V1 F3 1.9452(12) . ? V1 F5 1.9674(12) . ? V1 F6 1.9689(12) . ? V1 F4 1.9985(12) . ? V1 F1 2.0179(12) . ? N1 C1 1.514(2) . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? C1 C2 1.536(3) . ? C1 H1D 0.9700 . ? C1 H1E 0.9700 . ? C2 N2 1.510(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? N2 C3 1.517(2) . ? N2 H2C 0.9000 . ? N2 H2D 0.9000 . ? C3 C4 1.539(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N3 1.507(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? N3 H3C 0.8900 . ? N3 H3D 0.8900 . ? N3 H3E 0.8900 . ? 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 F2 V1 F3 95.83(6) . . ? F2 V1 F5 89.74(6) . . ? F3 V1 F5 173.27(5) . . ? F2 V1 F6 90.63(6) . . ? F3 V1 F6 90.27(5) . . ? F5 V1 F6 93.46(5) . . ? F2 V1 F4 175.44(5) . . ? F3 V1 F4 88.71(5) . . ? F5 V1 F4 85.76(5) . . ? F6 V1 F4 88.89(5) . . ? F2 V1 F1 94.23(6) . . ? F3 V1 F1 86.69(5) . . ? F5 V1 F1 89.14(5) . . ? F6 V1 F1 174.50(5) . . ? F4 V1 F1 86.46(5) . . ? C1 N1 H1A 109.5 . . ? C1 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? N1 C1 C2 113.49(15) . . ? N1 C1 H1D 108.9 . . ? C2 C1 H1D 108.9 . . ? N1 C1 H1E 108.9 . . ? C2 C1 H1E 108.9 . . ? H1D C1 H1E 107.7 . . ? N2 C2 C1 114.05(16) . . ? N2 C2 H2A 108.7 . . ? C1 C2 H2A 108.7 . . ? N2 C2 H2B 108.7 . . ? C1 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? C2 N2 C3 113.73(15) . . ? C2 N2 H2C 108.8 . . ? C3 N2 H2C 108.8 . . ? C2 N2 H2D 108.8 . . ? C3 N2 H2D 108.8 . . ? H2C N2 H2D 107.7 . . ? N2 C3 C4 111.99(15) . . ? N2 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? N2 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? N3 C4 C3 107.71(15) . . ? N3 C4 H4A 110.2 . . ? C3 C4 H4A 110.2 . . ? N3 C4 H4B 110.2 . . ? C3 C4 H4B 110.2 . . ? H4A C4 H4B 108.5 . . ? C4 N3 H3C 109.5 . . ? C4 N3 H3D 109.5 . . ? H3C N3 H3D 109.5 . . ? C4 N3 H3E 109.5 . . ? H3C N3 H3E 109.5 . . ? H3D N3 H3E 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A F2 0.89 2.11 2.868(2) 142.6 4_565 N1 H1B F1 0.89 2.10 2.843(2) 140.1 3_655 N2 H2D F4 0.90 1.87 2.692(2) 150.6 3_655 N2 H2D F1 0.90 2.46 2.999(2) 119.1 3_655 N1 H1C F5 0.89 1.99 2.744(2) 141.3 . N2 H2C F1 0.90 1.74 2.638(2) 175.5 . N3 H3C F6 0.89 1.86 2.697(2) 155.2 3_656 N3 H3D F4 0.89 2.03 2.840(2) 151.5 2_645 N3 H3E F3 0.89 1.81 2.685(2) 169.0 1_455 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.11 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.562 _refine_diff_density_min -0.601 _refine_diff_density_rms 0.091 #===end data_5 _database_code_depnum_ccdc_archive 'CCDC 634289' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H10 N2, F6 H4 O4 V2' _chemical_formula_sum 'C10 H14 F6 N2 O4 V2' _chemical_formula_weight 442.11 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' F F 0.0171 0.0103 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.5691(18) _cell_length_b 7.181(2) _cell_length_c 9.391(3) _cell_angle_alpha 101.073(12) _cell_angle_beta 97.506(11) _cell_angle_gamma 95.107(10) _cell_volume 362.9(2) _cell_formula_units_Z 1 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 1604 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 27.15 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.023 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 1.378 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7530 _exptl_absorpt_correction_T_max 0.7590 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Confocal optics' _diffrn_measurement_device_type 'CCD area Detector' _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2411 _diffrn_reflns_av_R_equivalents 0.0150 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 27.80 _reflns_number_total 1392 _reflns_number_gt 1370 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0605P)^2^+0.5220P] 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 1392 _refine_ls_number_parameters 117 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0321 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.1381 _refine_ls_wR_factor_gt 0.1376 _refine_ls_goodness_of_fit_ref 1.457 _refine_ls_restrained_S_all 1.457 _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 0.08616(8) 0.70296(6) 0.62326(5) 0.0058(3) Uani 1 1 d . . . F1 F 0.0706(3) 0.5570(2) 0.39585(19) 0.0085(4) Uani 1 1 d . . . F2 F 0.4077(3) 0.6164(3) 0.6469(2) 0.0103(4) Uani 1 1 d . . . F3 F 0.2398(3) 0.9144(3) 0.5620(2) 0.0119(4) Uani 1 1 d . . . O2 O -0.2362(4) 0.7799(3) 0.5423(3) 0.0097(5) Uani 1 1 d . . . O1 O 0.0702(4) 0.7765(3) 0.7941(2) 0.0127(5) Uani 1 1 d . . . N1 N 0.4696(5) 0.3368(4) 0.7782(3) 0.0116(6) Uani 1 1 d . . . H1N H 0.4623 0.4201 0.7236 0.014 Uiso 1 1 calc R . . C1 C 0.6339(7) 0.2145(5) 0.7644(4) 0.0181(7) Uani 1 1 d . . . H1 H 0.7390 0.2191 0.6956 0.022 Uiso 1 1 calc R . . C2 C 0.6502(7) 0.0805(5) 0.8514(4) 0.0161(7) Uani 1 1 d . . . H2 H 0.7663 -0.0047 0.8416 0.019 Uiso 1 1 calc R . . C3 C 0.4933(5) 0.0729(4) 0.9533(3) 0.0092(6) Uani 1 1 d . . . C4 C 0.3237(8) 0.2025(7) 0.9637(5) 0.0369(13) Uani 1 1 d . . . H4 H 0.2152 0.2011 1.0310 0.044 Uiso 1 1 calc R . . C5 C 0.3160(8) 0.3330(7) 0.8747(5) 0.0346(11) Uani 1 1 d . . . H5 H 0.2018 0.4200 0.8819 0.042 Uiso 1 1 calc R . . H1A H -0.245(9) 0.872(8) 0.512(6) 0.028(13) Uiso 1 1 d . . . H2A H -0.362(10) 0.737(7) 0.572(6) 0.029(13) 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 0.0055(4) 0.0057(3) 0.0072(4) 0.0030(2) 0.0014(2) 0.0012(2) F1 0.0093(9) 0.0080(9) 0.0099(9) 0.0045(7) 0.0040(6) 0.0007(7) F2 0.0074(10) 0.0104(9) 0.0157(10) 0.0080(7) 0.0024(7) 0.0028(7) F3 0.0095(10) 0.0085(9) 0.0191(10) 0.0074(7) 0.0016(7) -0.0005(7) O2 0.0065(12) 0.0099(11) 0.0164(12) 0.0090(9) 0.0041(8) 0.0033(8) O1 0.0136(12) 0.0140(11) 0.0099(11) 0.0007(9) 0.0015(8) 0.0020(8) N1 0.0153(15) 0.0111(13) 0.0092(13) 0.0070(10) -0.0009(10) -0.0004(10) C1 0.028(2) 0.0159(17) 0.0171(17) 0.0100(13) 0.0151(14) 0.0056(14) C2 0.0232(19) 0.0130(16) 0.0181(17) 0.0090(13) 0.0121(13) 0.0085(13) C3 0.0082(16) 0.0112(15) 0.0088(14) 0.0057(12) 0.0000(11) -0.0012(11) C4 0.034(3) 0.056(3) 0.048(3) 0.045(2) 0.033(2) 0.033(2) C5 0.031(2) 0.049(3) 0.047(3) 0.040(2) 0.0251(19) 0.0311(19) _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 1.606(2) . ? V1 F3 1.8975(19) . ? V1 F2 1.9468(19) . ? V1 F1 1.9543(18) 2_566 ? V1 O2 2.022(2) . ? V1 F1 2.1778(19) . ? F1 V1 1.9543(18) 2_566 ? O2 H1A 0.77(5) . ? O2 H2A 0.84(6) . ? N1 C1 1.325(5) . ? N1 C5 1.327(5) . ? N1 H1N 0.8600 . ? C1 C2 1.378(5) . ? C1 H1 0.9300 . ? C2 C3 1.382(5) . ? C2 H2 0.9300 . ? C3 C4 1.384(5) . ? C3 C3 1.490(6) 2_657 ? C4 C5 1.371(5) . ? C4 H4 0.9300 . ? C5 H5 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 F3 105.62(11) . . ? O1 V1 F2 97.77(10) . . ? F3 V1 F2 86.24(8) . . ? O1 V1 F1 97.23(10) . 2_566 ? F3 V1 F1 157.15(9) . 2_566 ? F2 V1 F1 91.03(8) . 2_566 ? O1 V1 O2 97.17(11) . . ? F3 V1 O2 87.41(9) . . ? F2 V1 O2 164.86(10) . . ? F1 V1 O2 89.50(9) 2_566 . ? O1 V1 F1 169.80(10) . . ? F3 V1 F1 84.55(8) . . ? F2 V1 F1 83.55(8) . . ? F1 V1 F1 72.60(8) 2_566 . ? O2 V1 F1 82.18(9) . . ? V1 F1 V1 107.40(8) 2_566 . ? V1 O2 H1A 122(4) . . ? V1 O2 H2A 118(3) . . ? H1A O2 H2A 116(5) . . ? C1 N1 C5 121.2(3) . . ? C1 N1 H1N 119.4 . . ? C5 N1 H1N 119.4 . . ? N1 C1 C2 120.5(3) . . ? N1 C1 H1 119.8 . . ? C2 C1 H1 119.8 . . ? C1 C2 C3 119.8(3) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C2 C3 C4 117.9(3) . . ? C2 C3 C3 120.4(4) . 2_657 ? C4 C3 C3 121.7(4) . 2_657 ? C5 C4 C3 119.8(4) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? N1 C5 C4 120.8(3) . . ? N1 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N F2 0.86 1.73 2.575(3) 165.5 . O2 H1A F3 0.77(5) 1.80(6) 2.571(3) 175(5) 2_576 O2 H2A F2 0.84(6) 1.78(6) 2.611(3) 169(5) 1_455 _diffrn_measured_fraction_theta_max 0.788 _diffrn_reflns_theta_full 27.80 _diffrn_measured_fraction_theta_full 0.778 _refine_diff_density_max 0.682 _refine_diff_density_min -0.624 _refine_diff_density_rms 0.216 #===end data_6 _database_code_depnum_ccdc_archive 'CCDC 634290' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H18 F6 N2 O4 V2' _chemical_formula_weight 398.10 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' F F 0.0171 0.0103 '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 7.0882(19) _cell_length_b 21.769(5) _cell_length_c 12.964(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.950(8) _cell_angle_gamma 90.00 _cell_volume 1975.9(9) _cell_formula_units_Z 6 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour turquoise _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.1500 _exptl_crystal_size_min 0.1500 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.007 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 1.506 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71070 _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 12036 _diffrn_reflns_av_R_equivalents 0.0492 _diffrn_reflns_av_sigmaI/netI 0.0498 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3545 _reflns_number_gt 1161 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0955P)^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 SHELXL _refine_ls_extinction_coef 0.0051(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3545 _refine_ls_number_parameters 252 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0956 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1857 _refine_ls_wR_factor_gt 0.1552 _refine_ls_goodness_of_fit_ref 0.920 _refine_ls_restrained_S_all 0.921 _refine_ls_shift/su_max 0.080 _refine_ls_shift/su_mean 0.001 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 0.08838(11) 0.49232(3) 0.62409(6) 0.0067(3) Uani 1 1 d . . . V2 V 0.08817(11) 0.34101(4) 0.12469(6) 0.0087(3) Uani 1 1 d . . . V3 V -0.08823(11) 0.32567(4) -0.12421(6) 0.0066(3) Uani 1 1 d . . . F1 F 0.1658(4) 0.49104(11) 0.48601(19) 0.0086(6) Uani 1 1 d . . . F2 F -0.0132(4) 0.40912(11) 0.6086(2) 0.0115(6) Uani 1 1 d . . . F3 F 0.1113(4) 0.58024(12) 0.62821(19) 0.0151(7) Uani 1 1 d . . . F4 F 0.1682(3) 0.34241(12) -0.0133(2) 0.0113(7) Uani 1 1 d . . . F5 F -0.1672(4) 0.32457(11) 0.0147(2) 0.0095(7) Uani 1 1 d . . . F6 F 0.1099(4) 0.25289(12) 0.1292(2) 0.0162(7) Uani 1 1 d . . . F7 F -0.0125(4) 0.42378(12) 0.1099(2) 0.0148(7) Uani 1 1 d . . . F8 F 0.0128(3) 0.24263(11) -0.1090(2) 0.0102(6) Uani 1 1 d . . . F9 F -0.1101(4) 0.41426(11) -0.1283(2) 0.0137(7) Uani 1 1 d . . . O1 O 0.2902(5) 0.47510(16) 0.6904(2) 0.0164(8) Uani 1 1 d . . . O2 O 0.2908(5) 0.35805(16) 0.1915(3) 0.0233(9) Uani 1 1 d . . . O3 O -0.2920(4) 0.30793(15) -0.1917(3) 0.0162(8) Uani 1 1 d . . . OW1 O -0.0764(5) 0.50068(13) 0.7378(3) 0.0106(8) Uani 1 1 d . . . OW2 O -0.0769(5) 0.33298(14) 0.2390(3) 0.0126(8) Uani 1 1 d . . . OW3 O 0.0758(5) 0.33391(14) -0.2382(3) 0.0104(8) Uani 1 1 d . . . N1 N 0.3552(6) 0.19847(18) 0.0063(3) 0.0159(10) Uiso 1 1 d . . . H4 H 0.2510 0.2223 0.0100 0.024 Uiso 1 1 calc R A 1 N2 N 0.6444(6) 0.13530(18) -0.0062(3) 0.0143(9) Uiso 1 1 d . . . H5 H 0.7500 0.1120 -0.0094 0.021 Uiso 1 1 calc R B 1 C1A C 0.7115(13) 0.1955(4) 0.0393(7) 0.011(2) Uiso 0.50 1 d P C 1 H6A H 0.8127 0.2120 0.0050 0.013 Uiso 0.50 1 calc PR C 1 H7A H 0.7578 0.1917 0.1135 0.013 Uiso 0.50 1 calc PR C 1 C2A C 0.5358(15) 0.2357(5) 0.0199(9) 0.022(2) Uiso 0.50 1 d P C 1 H8A H 0.5364 0.2636 0.0782 0.026 Uiso 0.50 1 calc PR C 1 H9A H 0.5393 0.2601 -0.0424 0.026 Uiso 0.50 1 calc PR C 1 C3A C 0.3832(14) 0.1488(4) 0.0937(8) 0.016(2) Uiso 0.50 1 d P C 1 H10A H 0.4280 0.1675 0.1609 0.019 Uiso 0.50 1 calc PR C 1 H11A H 0.2638 0.1278 0.0973 0.019 Uiso 0.50 1 calc PR C 1 C4A C 0.5325(16) 0.1037(5) 0.0643(9) 0.028(3) Uiso 0.50 1 d P C 1 H12A H 0.6159 0.0901 0.1266 0.033 Uiso 0.50 1 calc PR C 1 H13A H 0.4696 0.0679 0.0299 0.033 Uiso 0.50 1 calc PR C 1 C5A C 0.3452(18) 0.1689(6) -0.0973(10) 0.031(3) Uiso 0.50 1 d P C 1 H14A H 0.3165 0.1996 -0.1517 0.037 Uiso 0.50 1 calc PR C 1 H15A H 0.2434 0.1387 -0.1065 0.037 Uiso 0.50 1 calc PR C 1 C6A C 0.5394(17) 0.1369(6) -0.1071(9) 0.030(3) Uiso 0.50 1 d P C 1 H16A H 0.5176 0.0957 -0.1345 0.036 Uiso 0.50 1 calc PR C 1 H17A H 0.6077 0.1601 -0.1536 0.036 Uiso 0.50 1 calc PR C 1 C1B C 0.4609(13) 0.0957(4) -0.0238(8) 0.014(2) Uiso 0.50 1 d P C 2 H6B H 0.4604 0.0699 -0.0848 0.017 Uiso 0.50 1 calc PR C 2 H7B H 0.4568 0.0694 0.0362 0.017 Uiso 0.50 1 calc PR C 2 C2B C 0.2890(15) 0.1376(5) -0.0395(8) 0.019(2) Uiso 0.50 1 d P C 2 H8B H 0.2398 0.1418 -0.1133 0.023 Uiso 0.50 1 calc PR C 2 H9B H 0.1887 0.1211 -0.0045 0.023 Uiso 0.50 1 calc PR C 2 C3B C 0.6530(17) 0.1669(5) 0.0969(9) 0.027(3) Uiso 0.50 1 d P C 2 H10B H 0.7503 0.1985 0.1031 0.032 Uiso 0.50 1 calc PR C 2 H11B H 0.6888 0.1374 0.1526 0.032 Uiso 0.50 1 calc PR C 2 C4B C 0.4644(17) 0.1953(6) 0.1087(9) 0.031(3) Uiso 0.50 1 d P C 2 H12B H 0.3988 0.1704 0.1540 0.038 Uiso 0.50 1 calc PR C 2 H13B H 0.4832 0.2361 0.1386 0.038 Uiso 0.50 1 calc PR C 2 C5B C 0.6129(15) 0.1837(5) -0.0918(8) 0.018(2) Uiso 0.50 1 d P C 2 H14B H 0.5700 0.1641 -0.1585 0.022 Uiso 0.50 1 calc PR C 2 H15B H 0.7325 0.2045 -0.0961 0.022 Uiso 0.50 1 calc PR C 2 C6B C 0.4618(14) 0.2313(5) -0.0687(8) 0.019(2) Uiso 0.50 1 d P C 2 H16B H 0.5226 0.2682 -0.0374 0.023 Uiso 0.50 1 calc PR C 2 H17B H 0.3770 0.2423 -0.1321 0.023 Uiso 0.50 1 calc PR C 2 N3 N -0.3486(13) 0.4647(4) 0.0080(7) 0.007(3) Uiso 0.50 1 d PD D 3 H3 H -0.2412 0.4424 0.0042 0.010 Uiso 0.50 1 calc PR D 3 C7 C -0.2932(13) 0.5281(4) 0.0482(7) 0.014(2) Uiso 0.50 1 d PD D 3 H18 H -0.1943 0.5445 0.0119 0.016 Uiso 0.50 1 calc PR D 3 H19 H -0.2429 0.5262 0.1221 0.016 Uiso 0.50 1 calc PR D 3 C8 C -0.4668(16) 0.4700(6) -0.1012(8) 0.036(3) Uiso 0.50 1 d PD D 3 H20 H -0.4823 0.4298 -0.1336 0.044 Uiso 0.50 1 calc PR D 3 H21 H -0.4016 0.4964 -0.1447 0.044 Uiso 0.50 1 calc PR D 3 C9 C -0.4620(13) 0.4339(4) 0.0810(7) 0.018(2) Uiso 0.50 1 d PD D 3 H22 H -0.3811 0.4237 0.1462 0.022 Uiso 0.50 1 calc PR D 3 H23 H -0.5194 0.3964 0.0502 0.022 Uiso 0.50 1 calc PR D 3 C10 C -0.6637(16) 0.4973(5) -0.0913(8) 0.027(3) Uiso 0.50 1 d PD D 3 H24 H -0.7027 0.5269 -0.1464 0.033 Uiso 0.50 1 calc PR D 3 H25 H -0.7594 0.4652 -0.0954 0.033 Uiso 0.50 1 calc PR D 3 C11 C -0.6177(15) 0.4801(5) 0.1000(7) 0.024(2) Uiso 0.50 1 d PD D 3 H26 H -0.7385 0.4590 0.0988 0.029 Uiso 0.50 1 calc PR D 3 H27 H -0.5834 0.4991 0.1680 0.029 Uiso 0.50 1 calc PR D 3 C12 C -0.4678(12) 0.5704(4) 0.0307(7) 0.014(2) Uiso 0.50 1 d PD D 3 H28 H -0.4697 0.5970 0.0905 0.017 Uiso 0.50 1 calc PR D 3 H29 H -0.4666 0.5956 -0.0308 0.017 Uiso 0.50 1 calc PR D 3 N4 N -0.6373(11) 0.5285(3) 0.0163(6) 0.000(2) Uiso 0.50 1 d PD D 3 H30 H -0.7433 0.5513 0.0210 0.000 Uiso 0.50 1 calc PR D 3 HW1 H -0.0492 0.5277 0.7849 0.000 Uiso 1 1 d R . . HW2 H -0.0788 0.4730 0.7758 0.000 Uiso 1 1 d R . . HW3 H -0.0795 0.3603 0.2779 0.000 Uiso 1 1 d R . . HW4 H -0.0506 0.3049 0.2855 0.000 Uiso 1 1 d R . . HW5 H 0.0849 0.3060 -0.2780 0.000 Uiso 1 1 d R . . HW6 H 0.0540 0.3608 -0.2853 0.000 Uiso 1 1 d 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 0.0082(5) 0.0037(5) 0.0088(5) 0.0004(3) 0.0028(4) -0.0024(3) V2 0.0072(5) 0.0050(5) 0.0131(5) -0.0026(3) -0.0012(4) 0.0030(4) V3 0.0038(5) 0.0038(5) 0.0132(5) 0.0014(3) 0.0048(4) -0.0012(3) F1 0.0103(14) 0.0085(14) 0.0085(14) 0.0008(10) 0.0066(12) 0.0006(11) F2 0.0148(15) 0.0023(13) 0.0170(15) 0.0033(10) 0.0014(12) 0.0013(11) F3 0.0261(16) 0.0066(14) 0.0154(15) -0.0010(11) 0.0119(13) -0.0026(12) F4 0.0039(14) 0.0132(15) 0.0178(15) -0.0018(11) 0.0045(12) -0.0049(12) F5 0.0071(14) 0.0078(14) 0.0143(15) -0.0002(10) 0.0042(13) -0.0034(11) F6 0.0251(16) 0.0086(14) 0.0167(16) 0.0038(11) 0.0087(13) 0.0071(13) F7 0.0178(15) 0.0069(14) 0.0187(15) -0.0036(11) -0.0010(13) 0.0068(12) F8 0.0096(13) 0.0059(13) 0.0167(14) 0.0013(10) 0.0068(12) -0.0023(11) F9 0.0156(14) 0.0027(14) 0.0269(17) 0.0025(11) 0.0164(13) 0.0011(12) O1 0.0139(18) 0.023(2) 0.0126(18) 0.0049(15) 0.0020(15) -0.0021(16) O2 0.017(2) 0.016(2) 0.032(2) -0.0078(16) -0.0114(17) 0.0036(17) O3 0.0077(18) 0.0217(19) 0.019(2) 0.0021(15) 0.0029(16) -0.0064(16) OW1 0.0166(18) 0.0040(16) 0.0125(18) 0.0006(12) 0.0060(15) -0.0047(13) OW2 0.023(2) 0.0048(16) 0.0102(18) -0.0011(13) 0.0041(15) 0.0061(15) OW3 0.0134(18) 0.0054(16) 0.0147(18) 0.0011(13) 0.0093(15) 0.0013(14) _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 1.595(4) . ? V1 F3 1.921(3) . ? V1 F2 1.948(3) . ? V1 F1 1.953(2) . ? V1 OW1 2.026(3) . ? V1 F1 2.148(3) 3_566 ? V2 O2 1.601(4) . ? V2 F6 1.925(3) . ? V2 F7 1.936(3) . ? V2 F4 1.960(3) . ? V2 OW2 2.034(3) . ? V2 F5 2.153(3) . ? V3 O3 1.615(3) . ? V3 F9 1.935(3) . ? V3 F8 1.943(3) . ? V3 F5 1.967(2) . ? V3 OW3 2.025(3) . ? V3 F4 2.166(3) . ? F1 V1 2.148(3) 3_566 ? OW1 HW1 0.8485 . ? OW1 HW2 0.7805 . ? OW2 HW3 0.7819 . ? OW2 HW4 0.8580 . ? OW3 HW5 0.8061 . ? OW3 HW6 0.8429 . ? N1 C4B 1.430(13) . ? N1 C5A 1.481(12) . ? N1 C2B 1.497(11) . ? N1 C6B 1.502(10) . ? N1 C2A 1.502(11) . ? N1 C3A 1.556(10) . ? N1 H4 0.9100 . ? N2 C6A 1.401(13) . ? N2 C4A 1.472(11) . ? N2 C1A 1.484(10) . ? N2 C3B 1.496(12) . ? N2 C5B 1.522(11) . ? N2 C1B 1.547(10) . ? N2 H5 0.9100 . ? C1A C2A 1.510(14) . ? C1A H6A 0.9700 . ? C1A H7A 0.9700 . ? C2A H8A 0.9700 . ? C2A H9A 0.9700 . ? C3A C4A 1.535(14) . ? C3A H10A 0.9700 . ? C3A H11A 0.9700 . ? C4A H12A 0.9700 . ? C4A H13A 0.9700 . ? C5A C6A 1.565(16) . ? C5A H14A 0.9700 . ? C5A H15A 0.9700 . ? C6A H16A 0.9700 . ? C6A H17A 0.9700 . ? C1B C2B 1.510(14) . ? C1B H6B 0.9700 . ? C1B H7B 0.9700 . ? C2B H8B 0.9700 . ? C2B H9B 0.9700 . ? C3B C4B 1.503(16) . ? C3B H10B 0.9700 . ? C3B H11B 0.9700 . ? C4B H12B 0.9700 . ? C4B H13B 0.9700 . ? C5B C6B 1.551(13) . ? C5B H14B 0.9700 . ? C5B H15B 0.9700 . ? C6B H16B 0.9700 . ? C6B H17B 0.9700 . ? N3 C9 1.493(10) . ? N3 C7 1.506(10) . ? N3 C8 1.533(12) . ? N3 H3 0.9100 . ? C7 C12 1.529(13) . ? C7 H18 0.9700 . ? C7 H19 0.9700 . ? C8 C10 1.540(16) . ? C8 H20 0.9700 . ? C8 H21 0.9700 . ? C9 C11 1.542(14) . ? C9 H22 0.9700 . ? C9 H23 0.9700 . ? C10 N4 1.538(11) . ? C10 H24 0.9700 . ? C10 H25 0.9700 . ? C11 N4 1.503(11) . ? C11 H26 0.9700 . ? C11 H27 0.9700 . ? C12 N4 1.496(10) . ? C12 H28 0.9700 . ? C12 H29 0.9700 . ? N4 H30 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 F3 98.88(15) . . ? O1 V1 F2 97.08(15) . . ? F3 V1 F2 163.27(12) . . ? O1 V1 F1 97.69(14) . . ? F3 V1 F1 90.29(10) . . ? F2 V1 F1 92.52(10) . . ? O1 V1 OW1 101.52(15) . . ? F3 V1 OW1 86.91(11) . . ? F2 V1 OW1 85.02(11) . . ? F1 V1 OW1 160.79(14) . . ? O1 V1 F1 170.77(14) . 3_566 ? F3 V1 F1 84.78(11) . 3_566 ? F2 V1 F1 80.20(11) . 3_566 ? F1 V1 F1 73.73(11) . 3_566 ? OW1 V1 F1 87.09(12) . 3_566 ? O2 V2 F6 98.84(15) . . ? O2 V2 F7 97.11(15) . . ? F6 V2 F7 163.13(12) . . ? O2 V2 F4 97.34(16) . . ? F6 V2 F4 90.56(10) . . ? F7 V2 F4 92.84(11) . . ? O2 V2 OW2 101.24(17) . . ? F6 V2 OW2 86.84(11) . . ? F7 V2 OW2 84.69(11) . . ? F4 V2 OW2 161.43(14) . . ? O2 V2 F5 171.07(16) . . ? F6 V2 F5 84.80(11) . . ? F7 V2 F5 80.22(11) . . ? F4 V2 F5 74.39(10) . . ? OW2 V2 F5 87.06(12) . . ? O3 V3 F9 99.35(15) . . ? O3 V3 F8 96.73(15) . . ? F9 V3 F8 163.08(11) . . ? O3 V3 F5 97.79(14) . . ? F9 V3 F5 90.23(10) . . ? F8 V3 F5 92.78(11) . . ? O3 V3 OW3 101.08(15) . . ? F9 V3 OW3 86.81(11) . . ? F8 V3 OW3 84.96(11) . . ? F5 V3 OW3 161.13(14) . . ? O3 V3 F4 170.96(13) . . ? F9 V3 F4 84.59(11) . . ? F8 V3 F4 80.27(11) . . ? F5 V3 F4 73.95(10) . . ? OW3 V3 F4 87.21(12) . . ? V1 F1 V1 106.27(11) . 3_566 ? V3 F5 V2 105.94(11) . . ? V2 F4 V3 105.72(11) . . ? V1 OW1 HW1 119.6 . . ? V1 OW1 HW2 117.5 . . ? HW1 OW1 HW2 96.0 . . ? V2 OW2 HW3 118.6 . . ? V2 OW2 HW4 119.1 . . ? HW3 OW2 HW4 96.5 . . ? V3 OW3 HW5 120.8 . . ? V3 OW3 HW6 121.9 . . ? HW5 OW3 HW6 94.8 . . ? C4B N1 C5A 139.8(7) . . ? C4B N1 C2B 114.6(7) . . ? C5A N1 C2B 44.6(6) . . ? C4B N1 C6B 111.7(7) . . ? C5A N1 C6B 65.0(6) . . ? C2B N1 C6B 108.8(6) . . ? C4B N1 C2A 65.7(6) . . ? C5A N1 C2A 105.1(7) . . ? C2B N1 C2A 137.1(6) . . ? C6B N1 C2A 46.7(6) . . ? C4B N1 C3A 45.7(6) . . ? C5A N1 C3A 110.0(7) . . ? C2B N1 C3A 70.8(6) . . ? C6B N1 C3A 141.4(6) . . ? C2A N1 C3A 106.2(6) . . ? C4B N1 H4 107.8 . . ? C5A N1 H4 111.8 . . ? C2B N1 H4 108.6 . . ? C6B N1 H4 104.9 . . ? C2A N1 H4 111.8 . . ? C3A N1 H4 111.8 . . ? C6A N2 C4A 109.4(7) . . ? C6A N2 C1A 116.1(7) . . ? C4A N2 C1A 109.6(6) . . ? C6A N2 C3B 139.9(7) . . ? C4A N2 C3B 67.1(7) . . ? C1A N2 C3B 43.4(5) . . ? C6A N2 C5B 46.0(6) . . ? C4A N2 C5B 138.2(7) . . ? C1A N2 C5B 71.4(6) . . ? C3B N2 C5B 108.3(7) . . ? C6A N2 C1B 64.2(6) . . ? C4A N2 C1B 46.3(6) . . ? C1A N2 C1B 139.4(6) . . ? C3B N2 C1B 107.7(6) . . ? C5B N2 C1B 104.7(6) . . ? C6A N2 H5 107.1 . . ? C4A N2 H5 107.1 . . ? C1A N2 H5 107.1 . . ? C3B N2 H5 112.1 . . ? C5B N2 H5 112.4 . . ? C1B N2 H5 111.2 . . ? N2 C1A C2A 103.9(8) . . ? N2 C1A H6A 111.0 . . ? C2A C1A H6A 111.0 . . ? N2 C1A H7A 111.0 . . ? C2A C1A H7A 111.0 . . ? H6A C1A H7A 109.0 . . ? N1 C2A C1A 111.9(8) . . ? N1 C2A H8A 109.2 . . ? C1A C2A H8A 109.2 . . ? N1 C2A H9A 109.2 . . ? C1A C2A H9A 109.2 . . ? H8A C2A H9A 107.9 . . ? C4A C3A N1 106.2(7) . . ? C4A C3A H10A 110.5 . . ? N1 C3A H10A 110.5 . . ? C4A C3A H11A 110.5 . . ? N1 C3A H11A 110.5 . . ? H10A C3A H11A 108.7 . . ? N2 C4A C3A 108.3(8) . . ? N2 C4A H12A 110.0 . . ? C3A C4A H12A 110.0 . . ? N2 C4A H13A 110.0 . . ? C3A C4A H13A 110.0 . . ? H12A C4A H13A 108.4 . . ? N1 C5A C6A 110.4(10) . . ? N1 C5A H14A 109.6 . . ? C6A C5A H14A 109.6 . . ? N1 C5A H15A 109.6 . . ? C6A C5A H15A 109.6 . . ? H14A C5A H15A 108.1 . . ? N2 C6A C5A 106.4(8) . . ? N2 C6A H16A 110.5 . . ? C5A C6A H16A 110.5 . . ? N2 C6A H17A 110.5 . . ? C5A C6A H17A 110.5 . . ? H16A C6A H17A 108.6 . . ? C2B C1B N2 109.1(7) . . ? C2B C1B H6B 109.9 . . ? N2 C1B H6B 109.9 . . ? C2B C1B H7B 109.9 . . ? N2 C1B H7B 109.9 . . ? H6B C1B H7B 108.3 . . ? N1 C2B C1B 106.5(8) . . ? N1 C2B H8B 110.4 . . ? C1B C2B H8B 110.4 . . ? N1 C2B H9B 110.4 . . ? C1B C2B H9B 110.4 . . ? H8B C2B H9B 108.6 . . ? N2 C3B C4B 111.5(9) . . ? N2 C3B H10B 109.3 . . ? C4B C3B H10B 109.3 . . ? N2 C3B H11B 109.3 . . ? C4B C3B H11B 109.3 . . ? H10B C3B H11B 108.0 . . ? N1 C4B C3B 106.7(8) . . ? N1 C4B H12B 110.4 . . ? C3B C4B H12B 110.4 . . ? N1 C4B H13B 110.4 . . ? C3B C4B H13B 110.4 . . ? H12B C4B H13B 108.6 . . ? N2 C5B C6B 110.4(7) . . ? N2 C5B H14B 109.6 . . ? C6B C5B H14B 109.6 . . ? N2 C5B H15B 109.6 . . ? C6B C5B H15B 109.6 . . ? H14B C5B H15B 108.1 . . ? N1 C6B C5B 103.9(7) . . ? N1 C6B H16B 111.0 . . ? C5B C6B H16B 111.0 . . ? N1 C6B H17B 111.0 . . ? C5B C6B H17B 111.0 . . ? H16B C6B H17B 109.0 . . ? C9 N3 C7 109.3(7) . . ? C9 N3 C8 110.4(7) . . ? C7 N3 C8 109.0(8) . . ? C9 N3 H3 109.4 . . ? C7 N3 H3 109.4 . . ? C8 N3 H3 109.4 . . ? N3 C7 C12 109.8(7) . . ? N3 C7 H18 109.7 . . ? C12 C7 H18 109.7 . . ? N3 C7 H19 109.7 . . ? C12 C7 H19 109.7 . . ? H18 C7 H19 108.2 . . ? N3 C8 C10 108.9(8) . . ? N3 C8 H20 109.9 . . ? C10 C8 H20 109.9 . . ? N3 C8 H21 109.9 . . ? C10 C8 H21 109.9 . . ? H20 C8 H21 108.3 . . ? N3 C9 C11 106.1(7) . . ? N3 C9 H22 110.5 . . ? C11 C9 H22 110.5 . . ? N3 C9 H23 110.5 . . ? C11 C9 H23 110.5 . . ? H22 C9 H23 108.7 . . ? N4 C10 C8 105.2(8) . . ? N4 C10 H24 110.7 . . ? C8 C10 H24 110.7 . . ? N4 C10 H25 110.7 . . ? C8 C10 H25 110.7 . . ? H24 C10 H25 108.8 . . ? N4 C11 C9 109.3(7) . . ? N4 C11 H26 109.8 . . ? C9 C11 H26 109.8 . . ? N4 C11 H27 109.8 . . ? C9 C11 H27 109.8 . . ? H26 C11 H27 108.3 . . ? N4 C12 C7 105.6(7) . . ? N4 C12 H28 110.6 . . ? C7 C12 H28 110.6 . . ? N4 C12 H29 110.6 . . ? C7 C12 H29 110.6 . . ? H28 C12 H29 108.8 . . ? C12 N4 C11 110.8(8) . . ? C12 N4 C10 111.4(7) . . ? C11 N4 C10 109.2(7) . . ? C12 N4 H30 108.5 . . ? C11 N4 H30 108.5 . . ? C10 N4 H30 108.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H4 F6 0.91 2.08 2.797(4) 135.3 . N1 H4 F8 0.91 2.15 2.814(5) 129.3 . N2 H5 F3 0.91 2.07 2.791(4) 135.1 2_645 N2 H5 F2 0.91 2.14 2.814(5) 130.4 4_665 N3 H3 F7 0.91 1.99 2.690(10) 132.0 . N3 H3 F9 0.91 2.17 2.849(9) 131.3 . N4 H30 F9 0.91 2.01 2.770(8) 140.6 3_465 N4 H30 F7 0.91 2.29 2.942(9) 128.0 3_465 OW1 HW1 F7 0.85 1.73 2.572(4) 173.8 3_566 OW1 HW2 F9 0.78 1.82 2.597(4) 172.1 1_556 OW2 HW3 F3 0.78 1.81 2.593(4) 173.3 3_566 OW2 HW4 F8 0.86 1.72 2.570(4) 171.6 4_566 OW3 HW5 F6 0.81 1.79 2.592(4) 176.9 4_565 OW3 HW6 F2 0.84 1.74 2.576(4) 172.2 1_554 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.862 _refine_diff_density_min -0.696 _refine_diff_density_rms 0.125 #===end data_7 _database_code_depnum_ccdc_archive 'CCDC 634291' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H22 N4, F8 O2 V2' _chemical_formula_sum 'C6 H22 F8 N4 O2 V2' _chemical_formula_weight 436.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source V V 0.3005 0.5294 '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' F F 0.0171 0.0103 '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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 7.9286(19) _cell_length_b 10.591(3) _cell_length_c 8.497(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.834(6) _cell_angle_gamma 90.00 _cell_volume 706.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 1297 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 25.32 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.100 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.049 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 1.425 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.771 _exptl_absorpt_correction_T_max 0.866 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Confocal Optics' _diffrn_measurement_device_type 'CCD Area detector' _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4150 _diffrn_reflns_av_R_equivalents 0.0557 _diffrn_reflns_av_sigmaI/netI 0.1019 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 25.32 _reflns_number_total 1290 _reflns_number_gt 1203 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku., 2004)' _computing_data_reduction 'CrystalClear (Rigaku., 2004)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0677P)^2^+0.9429P] 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 1290 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1730 _refine_ls_wR_factor_gt 0.1325 _refine_ls_goodness_of_fit_ref 1.602 _refine_ls_restrained_S_all 1.602 _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 0.13502(8) 0.41665(6) 0.41046(8) 0.0071(3) Uani 1 1 d . . . F1 F -0.0499(3) 0.3973(2) 0.2317(3) 0.0111(6) Uani 1 1 d . . . F2 F -0.0229(3) 0.3995(2) 0.5691(3) 0.0103(6) Uani 1 1 d . . . F3 F 0.2570(3) 0.4984(2) 0.2591(3) 0.0138(6) Uani 1 1 d . . . F4 F 0.3127(3) 0.4723(2) 0.5713(3) 0.0099(6) Uani 1 1 d . . . O1 O 0.1971(4) 0.2722(3) 0.4042(4) 0.0114(7) Uani 1 1 d . . . N1 N 0.5691(4) 0.2960(3) 0.5617(4) 0.0091(7) Uani 1 1 d . . . H1A H 0.6506 0.3523 0.5910 0.014 Uiso 1 1 calc R . . H1B H 0.5758 0.2337 0.6325 0.014 Uiso 1 1 calc R . . H1C H 0.4678 0.3332 0.5564 0.014 Uiso 1 1 calc R . . C1 C 0.5908(6) 0.2434(4) 0.4019(5) 0.0116(9) Uani 1 1 d . . . H1D H 0.5799 0.3116 0.3249 0.014 Uiso 1 1 calc R . . H1E H 0.5000 0.1835 0.3700 0.014 Uiso 1 1 calc R . . C2 C 0.7613(5) 0.1777(4) 0.3977(5) 0.0119(9) Uani 1 1 d . . . H2A H 0.7895 0.1816 0.2902 0.014 Uiso 1 1 calc R . . H2B H 0.8486 0.2236 0.4658 0.014 Uiso 1 1 calc R . . N2 N 0.7651(4) 0.0425(3) 0.4496(4) 0.0078(7) Uani 1 1 d . . . H2C H 0.7457 0.0388 0.5514 0.009 Uiso 1 1 calc R . . H2D H 0.6806 0.0004 0.3902 0.009 Uiso 1 1 calc R . . C3 C 0.9304(5) -0.0213(4) 0.4353(4) 0.0068(8) Uani 1 1 d . . . H3A H 0.9639 -0.0023 0.3322 0.008 Uiso 1 1 calc R . . H3B H 0.9159 -0.1120 0.4421 0.008 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 0.0073(5) 0.0076(5) 0.0062(5) -0.0007(2) 0.0008(4) 0.0003(2) F1 0.0133(12) 0.0096(12) 0.0096(13) -0.0012(9) -0.0012(10) 0.0025(9) F2 0.0134(13) 0.0079(12) 0.0106(13) 0.0014(9) 0.0050(10) -0.0012(9) F3 0.0136(13) 0.0181(13) 0.0109(12) -0.0013(10) 0.0068(10) -0.0032(10) F4 0.0087(12) 0.0132(13) 0.0071(12) -0.0015(9) -0.0014(9) -0.0011(9) O1 0.0082(15) 0.0097(14) 0.0158(15) -0.0013(12) -0.0004(12) 0.0008(11) N1 0.0107(17) 0.0070(17) 0.0093(17) 0.0015(13) 0.0002(14) 0.0008(13) C1 0.014(2) 0.013(2) 0.0070(19) -0.0004(15) 0.0009(16) 0.0036(17) C2 0.016(2) 0.0079(19) 0.013(2) 0.0025(16) 0.0053(17) -0.0007(17) N2 0.0073(16) 0.0095(17) 0.0060(16) 0.0001(13) -0.0010(14) 0.0000(13) C3 0.0081(19) 0.011(2) 0.0015(17) -0.0007(14) 0.0001(17) 0.0017(15) _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 1.611(3) . ? V1 F4 1.917(2) . ? V1 F3 1.918(2) . ? V1 F2 1.969(2) . ? V1 F1 1.973(3) . ? V1 F2 2.157(2) 3_566 ? F2 V1 2.157(2) 3_566 ? N1 C1 1.500(5) . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? C1 C2 1.525(6) . ? C1 H1D 0.9700 . ? C1 H1E 0.9700 . ? C2 N2 1.497(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? N2 C3 1.493(5) . ? N2 H2C 0.9000 . ? N2 H2D 0.9000 . ? C3 C3 1.517(8) 3_756 ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? 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 F4 96.75(13) . . ? O1 V1 F3 102.86(13) . . ? F4 V1 F3 87.17(11) . . ? O1 V1 F2 99.24(13) . . ? F4 V1 F2 90.82(10) . . ? F3 V1 F2 157.89(11) . . ? O1 V1 F1 94.26(13) . . ? F4 V1 F1 167.87(10) . . ? F3 V1 F1 85.44(11) . . ? F2 V1 F1 92.42(11) . . ? O1 V1 F2 172.49(12) . 3_566 ? F4 V1 F2 86.31(10) . 3_566 ? F3 V1 F2 84.10(10) . 3_566 ? F2 V1 F2 73.80(10) . 3_566 ? F1 V1 F2 83.38(10) . 3_566 ? V1 F2 V1 106.20(10) . 3_566 ? C1 N1 H1A 109.5 . . ? C1 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? N1 C1 C2 113.7(4) . . ? N1 C1 H1D 108.8 . . ? C2 C1 H1D 108.8 . . ? N1 C1 H1E 108.8 . . ? C2 C1 H1E 108.8 . . ? H1D C1 H1E 107.7 . . ? N2 C2 C1 114.3(3) . . ? N2 C2 H2A 108.7 . . ? C1 C2 H2A 108.7 . . ? N2 C2 H2B 108.7 . . ? C1 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? C3 N2 C2 113.0(3) . . ? C3 N2 H2C 109.0 . . ? C2 N2 H2C 109.0 . . ? C3 N2 H2D 109.0 . . ? C2 N2 H2D 109.0 . . ? H2C N2 H2D 107.8 . . ? N2 C3 C3 111.5(4) . 3_756 ? N2 C3 H3A 109.3 . . ? C3 C3 H3A 109.3 3_756 . ? N2 C3 H3B 109.3 . . ? C3 C3 H3B 109.3 3_756 . ? H3A C3 H3B 108.0 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1C F4 0.89 1.93 2.770(4) 155.7 . N1 H1A F3 0.89 2.10 2.896(4) 148.7 3_666 N1 H1A F4 0.89 2.35 2.909(4) 120.5 3_666 N1 H1B F1 0.89 1.96 2.745(4) 145.8 4_666 N2 H2C F3 0.90 1.80 2.675(4) 163.9 4_666 N2 H2D F1 0.90 1.75 2.633(4) 168.2 2_545 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.32 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.936 _refine_diff_density_min -0.995 _refine_diff_density_rms 0.269 #===end data_8 _database_code_depnum_ccdc_archive 'CCDC 634292' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H42 F14 N8 O7 V4' _chemical_formula_weight 880.30 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' F F 0.0171 0.0103 '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 9.953(3) _cell_length_b 10.621(2) _cell_length_c 15.3669(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.139(8) _cell_angle_gamma 90.00 _cell_volume 1575.1(6) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Platelet _exptl_crystal_colour Blue _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.1000 _exptl_crystal_size_min 0.0300 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.856 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 1.279 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71070 _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 9732 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0264 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.34 _reflns_number_total 2873 _reflns_number_gt 2624 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0388P)^2^+2.3590P] 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 2873 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0377 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0832 _refine_ls_wR_factor_gt 0.0806 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.12299(5) 0.90531(4) 0.15412(3) 0.00896(15) Uani 1 1 d . . . V2 V -0.13278(5) 0.79467(4) -0.01935(3) 0.01009(15) Uani 1 1 d . . . F1 F 0.09879(17) 0.80048(14) 0.04548(10) 0.0146(6) Uani 1.000(7) 1 d . . . F2 F -0.10705(16) 0.88619(14) 0.09375(10) 0.0135(6) Uani 1.000(7) 1 d . . . F3 F 0.10255(17) 0.75700(14) 0.22120(10) 0.0146(6) Uani 1.000(7) 1 d . . . F4 F 0.05555(17) 0.99917(14) 0.24178(10) 0.0166(6) Uani 1.000(7) 1 d . . . F5 F -0.07167(18) 0.69965(14) -0.10762(10) 0.0173(6) Uani 1.000(7) 1 d . . . F6 F -0.12043(17) 0.64161(14) 0.04736(10) 0.0164(6) Uani 1.000(7) 1 d . . . F7 F -0.08386(17) 0.94368(14) -0.07728(10) 0.0162(6) Uani 1.000(7) 1 d . . . O1 O 0.2869(2) 0.92243(19) 0.18487(14) 0.0208(7) Uani 1.000(9) 1 d . . . O2 O -0.2981(2) 0.80153(18) -0.05591(13) 0.0172(7) Uani 1.000(9) 1 d . . . OW1 O 0.4615(6) 0.0940(5) 0.4994(4) 0.0369(12) Uani 0.50 1 d P . . OW2 O 0.2631(3) 0.5734(3) -0.09479(17) 0.0495(8) Uani 1 1 d . . . N1 N 0.3374(2) 0.4678(2) 0.28753(15) 0.0109(5) Uani 1 1 d . . . N2 N 0.1774(2) 0.2294(2) 0.28031(15) 0.0117(5) Uani 1 1 d . . . H2A H 0.1449 0.1559 0.2562 0.018 Uiso 1 1 calc R . . H2B H 0.1426 0.2914 0.2425 0.018 Uiso 1 1 calc R . . H2C H 0.1527 0.2405 0.3317 0.018 Uiso 1 1 calc R . . N3 N 0.1371(3) 0.5464(2) 0.12470(18) 0.0238(6) Uani 1 1 d . . . H3A H 0.0899 0.6044 0.0878 0.036 Uiso 1 1 calc R . . H3B H 0.1167 0.5521 0.1778 0.036 Uiso 1 1 calc R . . H3C H 0.1143 0.4702 0.1017 0.036 Uiso 1 1 calc R . . N4 N 0.1841(2) 0.6383(2) 0.38665(15) 0.0127(5) Uani 1 1 d . . . H4A H 0.1500 0.6553 0.4338 0.019 Uiso 1 1 calc R . . H4B H 0.1407 0.5716 0.3577 0.019 Uiso 1 1 calc R . . H4C H 0.1715 0.7043 0.3499 0.019 Uiso 1 1 calc R . . C1 C 0.3936(3) 0.3540(2) 0.33882(18) 0.0132(6) Uani 1 1 d . . . H1A H 0.3786 0.3611 0.3987 0.016 Uiso 1 1 calc R . . H1B H 0.4928 0.3515 0.3448 0.016 Uiso 1 1 calc R . . C2 C 0.3313(3) 0.2301(2) 0.29786(19) 0.0137(6) Uani 1 1 d . . . H2D H 0.3578 0.2159 0.2420 0.016 Uiso 1 1 calc R . . H2E H 0.3687 0.1617 0.3384 0.016 Uiso 1 1 calc R . . C3 C 0.3723(3) 0.4695(2) 0.19915(17) 0.0129(6) Uani 1 1 d . . . H3D H 0.3550 0.3869 0.1719 0.015 Uiso 1 1 calc R . . H3E H 0.4701 0.4878 0.2078 0.015 Uiso 1 1 calc R . . C4 C 0.2881(3) 0.5671(3) 0.13597(19) 0.0202(6) Uani 1 1 d . . . H4D H 0.3126 0.6508 0.1599 0.024 Uiso 1 1 calc R . . H4E H 0.3101 0.5618 0.0780 0.024 Uiso 1 1 calc R . . C5 C 0.3980(3) 0.5803(2) 0.33999(18) 0.0141(6) Uani 1 1 d . . . H5A H 0.3863 0.6524 0.3000 0.017 Uiso 1 1 calc R . . H5B H 0.4966 0.5669 0.3632 0.017 Uiso 1 1 calc R . . C6 C 0.3346(3) 0.6109(3) 0.41769(18) 0.0149(6) Uani 1 1 d . . . H6A H 0.3482 0.5403 0.4589 0.018 Uiso 1 1 calc R . . H6B H 0.3814 0.6834 0.4498 0.018 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 0.0102(3) 0.0090(2) 0.0074(2) 0.00031(16) 0.00153(18) -0.00047(16) V2 0.0102(3) 0.0114(2) 0.0081(2) -0.00110(16) 0.00133(18) 0.00023(16) F1 0.0181(10) 0.0139(9) 0.0124(9) -0.0004(6) 0.0050(7) 0.0008(6) F2 0.0155(10) 0.0138(9) 0.0115(9) -0.0005(6) 0.0042(7) 0.0003(6) F3 0.0180(10) 0.0133(9) 0.0124(9) 0.0035(6) 0.0035(7) 0.0010(6) F4 0.0230(10) 0.0144(9) 0.0130(9) -0.0026(6) 0.0057(7) -0.0015(6) F5 0.0208(10) 0.0172(9) 0.0141(9) -0.0039(6) 0.0048(7) 0.0008(7) F6 0.0178(10) 0.0149(9) 0.0157(9) 0.0031(6) 0.0027(7) -0.0006(6) F7 0.0199(10) 0.0144(9) 0.0137(9) 0.0033(6) 0.0030(7) -0.0015(6) O1 0.0149(13) 0.0244(12) 0.0216(12) 0.0018(9) 0.0015(9) -0.0022(8) O2 0.0150(12) 0.0183(11) 0.0168(12) 0.0015(8) 0.0007(9) 0.0001(8) OW1 0.039(3) 0.038(3) 0.036(3) -0.003(2) 0.014(2) -0.001(2) OW2 0.0454(18) 0.078(2) 0.0208(13) -0.0003(13) -0.0001(12) 0.0060(15) N1 0.0117(12) 0.0111(11) 0.0104(11) -0.0011(8) 0.0034(9) -0.0004(9) N2 0.0158(12) 0.0101(10) 0.0105(11) -0.0025(8) 0.0055(9) -0.0011(9) N3 0.0267(15) 0.0151(12) 0.0212(14) -0.0057(10) -0.0102(11) 0.0077(10) N4 0.0162(13) 0.0114(10) 0.0116(11) -0.0001(8) 0.0053(10) -0.0002(9) C1 0.0109(14) 0.0163(13) 0.0121(13) 0.0013(10) 0.0022(11) 0.0004(10) C2 0.0128(14) 0.0140(13) 0.0151(13) 0.0027(10) 0.0048(11) 0.0025(10) C3 0.0142(14) 0.0143(13) 0.0103(13) -0.0011(10) 0.0033(11) -0.0005(10) C4 0.0317(18) 0.0146(13) 0.0134(14) 0.0030(11) 0.0041(13) -0.0001(12) C5 0.0133(14) 0.0143(13) 0.0150(14) -0.0022(10) 0.0039(11) -0.0028(10) C6 0.0134(14) 0.0173(14) 0.0122(14) -0.0029(10) -0.0003(11) 0.0002(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 O1 1.595(2) . ? V1 F3 1.9203(15) . ? V1 F4 1.9237(16) . ? V1 F1 1.9719(16) . ? V1 F7 1.9731(16) 3_575 ? V1 F2 2.2596(18) . ? V2 O2 1.605(2) . ? V2 F5 1.9055(16) . ? V2 F6 1.9097(16) . ? V2 F7 1.9354(16) . ? V2 F2 1.9529(16) . ? V2 F1 2.2773(18) . ? F7 V1 1.9731(16) 3_575 ? N1 C1 1.476(3) . ? N1 C3 1.482(3) . ? N1 C5 1.484(3) . ? N2 C2 1.489(4) . ? N2 H2A 0.8900 . ? N2 H2B 0.8900 . ? N2 H2C 0.8900 . ? N3 C4 1.486(4) . ? N3 H3A 0.8900 . ? N3 H3B 0.8900 . ? N3 H3C 0.8900 . ? N4 C6 1.485(4) . ? N4 H4A 0.8900 . ? N4 H4B 0.8900 . ? N4 H4C 0.8900 . ? C1 C2 1.524(4) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2D 0.9700 . ? C2 H2E 0.9700 . ? C3 C4 1.524(4) . ? C3 H3D 0.9700 . ? C3 H3E 0.9700 . ? C4 H4D 0.9700 . ? C4 H4E 0.9700 . ? C5 C6 1.516(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? 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 F3 99.75(9) . . ? O1 V1 F4 103.90(9) . . ? F3 V1 F4 87.04(7) . . ? O1 V1 F1 102.70(9) . . ? F3 V1 F1 89.10(7) . . ? F4 V1 F1 153.39(7) . . ? O1 V1 F7 97.05(9) . 3_575 ? F3 V1 F7 163.07(7) . 3_575 ? F4 V1 F7 86.92(7) . 3_575 ? F1 V1 F7 89.25(7) . 3_575 ? O1 V1 F2 173.15(9) . . ? F3 V1 F2 85.25(6) . . ? F4 V1 F2 80.92(7) . . ? F1 V1 F2 72.53(6) . . ? F7 V1 F2 78.19(6) 3_575 . ? O2 V2 F5 104.66(9) . . ? O2 V2 F6 98.77(9) . . ? F5 V2 F6 86.64(7) . . ? O2 V2 F7 98.83(9) . . ? F5 V2 F7 86.89(7) . . ? F6 V2 F7 162.27(7) . . ? O2 V2 F2 100.91(9) . . ? F5 V2 F2 154.40(7) . . ? F6 V2 F2 88.21(7) . . ? F7 V2 F2 90.53(7) . . ? O2 V2 F1 173.31(8) . . ? F5 V2 F1 82.00(7) . . ? F6 V2 F1 82.11(6) . . ? F7 V2 F1 80.66(6) . . ? F2 V2 F1 72.45(6) . . ? V1 F1 V2 106.67(7) . . ? V2 F2 V1 108.03(7) . . ? V2 F7 V1 154.80(10) . 3_575 ? C1 N1 C3 110.9(2) . . ? C1 N1 C5 108.6(2) . . ? C3 N1 C5 109.5(2) . . ? C2 N2 H2A 109.5 . . ? C2 N2 H2B 109.5 . . ? H2A N2 H2B 109.5 . . ? C2 N2 H2C 109.5 . . ? H2A N2 H2C 109.5 . . ? H2B N2 H2C 109.5 . . ? C4 N3 H3A 109.5 . . ? C4 N3 H3B 109.5 . . ? H3A N3 H3B 109.5 . . ? C4 N3 H3C 109.5 . . ? H3A N3 H3C 109.5 . . ? H3B N3 H3C 109.5 . . ? C6 N4 H4A 109.5 . . ? C6 N4 H4B 109.5 . . ? H4A N4 H4B 109.5 . . ? C6 N4 H4C 109.5 . . ? H4A N4 H4C 109.5 . . ? H4B N4 H4C 109.5 . . ? N1 C1 C2 115.1(2) . . ? N1 C1 H1A 108.5 . . ? C2 C1 H1A 108.5 . . ? N1 C1 H1B 108.5 . . ? C2 C1 H1B 108.5 . . ? H1A C1 H1B 107.5 . . ? N2 C2 C1 112.1(2) . . ? N2 C2 H2D 109.2 . . ? C1 C2 H2D 109.2 . . ? N2 C2 H2E 109.2 . . ? C1 C2 H2E 109.2 . . ? H2D C2 H2E 107.9 . . ? N1 C3 C4 112.1(2) . . ? N1 C3 H3D 109.2 . . ? C4 C3 H3D 109.2 . . ? N1 C3 H3E 109.2 . . ? C4 C3 H3E 109.2 . . ? H3D C3 H3E 107.9 . . ? N3 C4 C3 110.9(2) . . ? N3 C4 H4D 109.5 . . ? C3 C4 H4D 109.5 . . ? N3 C4 H4E 109.5 . . ? C3 C4 H4E 109.5 . . ? H4D C4 H4E 108.1 . . ? N1 C5 C6 114.1(2) . . ? N1 C5 H5A 108.7 . . ? C6 C5 H5A 108.7 . . ? N1 C5 H5B 108.7 . . ? C6 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? N4 C6 C5 111.7(2) . . ? N4 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? N4 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 107.9 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3A F6 0.89 2.07 2.742(3) 131.4 . N3 H3A F1 0.89 2.19 2.947(3) 142.6 . N4 H4C F3 0.89 2.01 2.776(3) 143.7 . N2 H2A F4 0.89 1.87 2.729(3) 160.3 1_545 N2 H2B F5 0.89 2.02 2.712(3) 133.4 3_565 N3 H3C F5 0.89 1.86 2.690(3) 154.3 3_565 N2 H2C F2 0.89 2.04 2.770(3) 138.2 2_545 N2 H2C F6 0.89 2.23 2.990(3) 143.7 2_545 N4 H4B F2 0.89 2.16 2.821(3) 130.5 2_545 N4 H4A F1 0.89 1.96 2.849(3) 172.7 4_576 N4 H4A F7 0.89 2.52 2.983(3) 112.9 4_576 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.523 _refine_diff_density_min -0.476 _refine_diff_density_rms 0.077 #===end data_9 _database_code_depnum_ccdc_archive 'CCDC 634293' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H20 N3, 0.5(F14 O4 V4), H2 O' _chemical_formula_sum 'C6 H22 F7 N3 O3 V2' _chemical_formula_weight 419.15 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' F F 0.0171 0.0103 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.275(3) _cell_length_b 9.7060(19) _cell_length_c 10.2315(19) _cell_angle_alpha 63.134(19) _cell_angle_beta 85.33(3) _cell_angle_gamma 78.59(2) _cell_volume 718.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 2654 _cell_measurement_theta_min 2.4361 _cell_measurement_theta_max 25.3491 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.1000 _exptl_crystal_size_mid 0.1000 _exptl_crystal_size_min 0.1000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.937 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 1.392 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8670 _exptl_absorpt_correction_T_max 0.8730 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'ROTATING Anode' _diffrn_radiation_monochromator 'Confocal Optics' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4252 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0326 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 25.35 _reflns_number_total 2634 _reflns_number_gt 2223 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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.Two restraints have been used in this structure solution. These were distance restraints, of 0.85 Angstroms, with which two hydrogens attached to an Oxygen atom in a water molecule were restrained. ; _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^)+(0.0362P)^2^+0.8769P] 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 2634 _refine_ls_number_parameters 196 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0330 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0806 _refine_ls_wR_factor_gt 0.0796 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.052 _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 0.40401(5) -0.14673(5) 0.07206(4) 0.00974(13) Uani 1 1 d . . . V2 V 0.23861(5) 0.18024(5) 0.17905(4) 0.01192(14) Uani 1 1 d . . . F1 F 0.25615(18) -0.00255(17) 0.13748(16) 0.0161(3) Uani 1 1 d . . . F2 F 0.21063(17) -0.14142(17) -0.02569(16) 0.0160(3) Uani 1 1 d . . . F3 F 0.41064(17) 0.07681(16) -0.11345(15) 0.0132(3) Uani 1 1 d . . . F4 F 0.45396(18) 0.22681(17) 0.04617(15) 0.0153(3) Uani 1 1 d . . . F5 F 0.40034(19) 0.06448(18) 0.33467(16) 0.0192(4) Uani 1 1 d . . . F6 F 0.26291(18) 0.36633(17) 0.20086(16) 0.0176(3) Uani 1 1 d . . . F7 F 0.12994(19) 0.31732(18) -0.00665(16) 0.0188(3) Uani 1 1 d . . . O1 O 0.3988(2) -0.3051(2) 0.21856(19) 0.0186(4) Uani 1 1 d . . . O2 O 0.0734(2) 0.1473(2) 0.2759(2) 0.0181(4) Uani 1 1 d . . . O3 O 0.0297(3) 0.4858(2) 0.2997(2) 0.0218(5) Uani 1 1 d D . . H1 H 0.110(3) 0.448(4) 0.266(3) 0.026 Uiso 1 1 d D . . H2 H -0.030(4) 0.524(4) 0.235(3) 0.026 Uiso 1 1 d D . . N1 N 0.9465(3) -0.1711(3) 0.1729(2) 0.0186(5) Uani 1 1 d . . . H1A H 1.0418 -0.1972 0.1354 0.028 Uiso 1 1 calc R . . H1B H 0.9052 -0.0702 0.1183 0.028 Uiso 1 1 calc R . . H1C H 0.8758 -0.2298 0.1740 0.028 Uiso 1 1 calc R . . N2 N 0.5508(3) -0.2253(2) 0.5086(2) 0.0140(5) Uani 1 1 d . . . H2C H 0.5015 -0.1274 0.4478 0.017 Uiso 1 1 calc R . . H2D H 0.5811 -0.2238 0.5904 0.017 Uiso 1 1 calc R . . N3 N 0.2062(3) -0.3871(3) 0.9044(3) 0.0207(5) Uani 1 1 d . . . H3C H 0.1437 -0.2930 0.8800 0.031 Uiso 1 1 calc R . . H3D H 0.2448 -0.4259 0.9952 0.031 Uiso 1 1 calc R . . H3E H 0.1461 -0.4514 0.8997 0.031 Uiso 1 1 calc R . . C1 C 0.9745(3) -0.1980(3) 0.3249(3) 0.0179(6) Uani 1 1 d . . . H1D H 1.0534 -0.1355 0.3234 0.021 Uiso 1 1 calc R . . H1E H 1.0214 -0.3077 0.3836 0.021 Uiso 1 1 calc R . . C2 C 0.8163(3) -0.1553(3) 0.3954(3) 0.0193(6) Uani 1 1 d . . . H2A H 0.7594 -0.0522 0.3279 0.023 Uiso 1 1 calc R . . H2B H 0.8439 -0.1492 0.4827 0.023 Uiso 1 1 calc R . . C3 C 0.7004(3) -0.2726(3) 0.4369(3) 0.0150(6) Uani 1 1 d . . . H3A H 0.6686 -0.2766 0.3497 0.018 Uiso 1 1 calc R . . H3B H 0.7566 -0.3765 0.5032 0.018 Uiso 1 1 calc R . . C4 C 0.4297(3) -0.3342(3) 0.5480(3) 0.0188(6) Uani 1 1 d . . . H4A H 0.4882 -0.4416 0.5973 0.023 Uiso 1 1 calc R . . H4B H 0.3817 -0.3207 0.4587 0.023 Uiso 1 1 calc R . . C5 C 0.2926(4) -0.3076(4) 0.6458(3) 0.0233(6) Uani 1 1 d . . . H5A H 0.2516 -0.1957 0.6084 0.028 Uiso 1 1 calc R . . H5B H 0.2026 -0.3562 0.6418 0.028 Uiso 1 1 calc R . . C6 C 0.3456(3) -0.3724(4) 0.8019(3) 0.0256(7) Uani 1 1 d . . . H6A H 0.4143 -0.4750 0.8306 0.031 Uiso 1 1 calc R . . H6B H 0.4120 -0.3044 0.8096 0.031 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 0.0079(2) 0.0096(2) 0.0115(2) -0.00455(18) 0.00173(16) -0.00208(17) V2 0.0102(2) 0.0118(2) 0.0134(2) -0.00575(19) 0.00079(17) -0.00105(18) F1 0.0134(8) 0.0160(8) 0.0228(8) -0.0124(7) 0.0072(6) -0.0043(6) F2 0.0097(8) 0.0204(8) 0.0226(8) -0.0130(7) 0.0008(6) -0.0041(6) F3 0.0105(7) 0.0129(7) 0.0145(7) -0.0043(6) -0.0010(6) -0.0029(6) F4 0.0125(8) 0.0174(8) 0.0201(8) -0.0120(7) 0.0052(6) -0.0044(6) F5 0.0194(8) 0.0179(8) 0.0170(8) -0.0067(7) -0.0045(6) 0.0029(7) F6 0.0176(8) 0.0162(8) 0.0219(8) -0.0111(7) 0.0030(6) -0.0040(6) F7 0.0163(8) 0.0183(8) 0.0192(8) -0.0060(7) -0.0044(6) -0.0014(6) O1 0.0236(11) 0.0143(10) 0.0167(9) -0.0058(8) 0.0047(8) -0.0058(8) O2 0.0152(10) 0.0180(10) 0.0231(10) -0.0117(8) 0.0069(8) -0.0036(8) O3 0.0234(12) 0.0178(11) 0.0225(11) -0.0111(9) 0.0018(8) 0.0048(9) N1 0.0110(11) 0.0238(13) 0.0179(11) -0.0072(10) 0.0021(9) -0.0029(9) N2 0.0135(11) 0.0126(11) 0.0149(11) -0.0061(9) 0.0002(9) -0.0007(9) N3 0.0164(12) 0.0183(12) 0.0250(12) -0.0084(10) 0.0079(10) -0.0041(10) C1 0.0142(14) 0.0209(15) 0.0189(13) -0.0083(12) 0.0006(11) -0.0059(11) C2 0.0200(15) 0.0212(15) 0.0187(13) -0.0103(12) 0.0025(11) -0.0059(12) C3 0.0149(14) 0.0139(13) 0.0148(13) -0.0066(11) 0.0023(10) -0.0001(11) C4 0.0218(16) 0.0189(15) 0.0174(14) -0.0084(12) 0.0027(11) -0.0080(12) C5 0.0163(15) 0.0244(16) 0.0235(15) -0.0065(13) 0.0043(12) -0.0038(12) C6 0.0122(14) 0.046(2) 0.0229(15) -0.0201(14) 0.0054(12) -0.0046(13) _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 1.5949(19) . ? V1 F4 1.9250(15) 2_655 ? V1 F2 1.9351(16) . ? V1 F3 1.9416(15) 2_655 ? V1 F1 1.9846(16) . ? V1 F3 2.1497(16) . ? V2 O2 1.6185(19) . ? V2 F7 1.9258(17) . ? V2 F5 1.9297(17) . ? V2 F6 1.9667(15) . ? V2 F1 1.9798(15) . ? V2 F4 2.1440(17) . ? F3 V1 1.9416(15) 2_655 ? F4 V1 1.9250(15) 2_655 ? O3 H1 0.822(18) . ? O3 H2 0.763(18) . ? N1 C1 1.486(3) . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? N2 C3 1.488(3) . ? N2 C4 1.500(3) . ? N2 H2C 0.9000 . ? N2 H2D 0.9000 . ? N3 C6 1.478(3) . ? N3 H3C 0.8900 . ? N3 H3D 0.8900 . ? N3 H3E 0.8900 . ? C1 C2 1.519(4) . ? C1 H1D 0.9700 . ? C1 H1E 0.9700 . ? C2 C3 1.525(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.512(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.495(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? 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 F4 100.48(9) . 2_655 ? O1 V1 F2 99.06(9) . . ? F4 V1 F2 91.04(7) 2_655 . ? O1 V1 F3 101.07(9) . 2_655 ? F4 V1 F3 89.16(7) 2_655 2_655 ? F2 V1 F3 159.49(6) . 2_655 ? O1 V1 F1 97.32(8) . . ? F4 V1 F1 162.19(6) 2_655 . ? F2 V1 F1 85.51(7) . . ? F3 V1 F1 88.05(6) 2_655 . ? O1 V1 F3 174.99(8) . . ? F4 V1 F3 83.56(6) 2_655 . ? F2 V1 F3 83.74(7) . . ? F3 V1 F3 75.90(7) 2_655 . ? F1 V1 F3 78.69(6) . . ? O2 V2 F7 96.86(9) . . ? O2 V2 F5 98.76(9) . . ? F7 V2 F5 164.04(7) . . ? O2 V2 F6 96.59(8) . . ? F7 V2 F6 89.01(7) . . ? F5 V2 F6 85.99(7) . . ? O2 V2 F1 94.57(8) . . ? F7 V2 F1 90.79(7) . . ? F5 V2 F1 91.20(7) . . ? F6 V2 F1 168.79(6) . . ? O2 V2 F4 178.65(8) . . ? F7 V2 F4 81.80(7) . . ? F5 V2 F4 82.58(7) . . ? F6 V2 F4 83.57(6) . . ? F1 V2 F4 85.31(6) . . ? V2 F1 V1 145.30(8) . . ? V1 F3 V1 104.10(7) 2_655 . ? V1 F4 V2 139.61(8) 2_655 . ? H1 O3 H2 101(3) . . ? C1 N1 H1A 109.5 . . ? C1 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? C3 N2 C4 112.5(2) . . ? C3 N2 H2C 109.1 . . ? C4 N2 H2C 109.1 . . ? C3 N2 H2D 109.1 . . ? C4 N2 H2D 109.1 . . ? H2C N2 H2D 107.8 . . ? C6 N3 H3C 109.5 . . ? C6 N3 H3D 109.5 . . ? H3C N3 H3D 109.5 . . ? C6 N3 H3E 109.5 . . ? H3C N3 H3E 109.5 . . ? H3D N3 H3E 109.5 . . ? N1 C1 C2 112.1(2) . . ? N1 C1 H1D 109.2 . . ? C2 C1 H1D 109.2 . . ? N1 C1 H1E 109.2 . . ? C2 C1 H1E 109.2 . . ? H1D C1 H1E 107.9 . . ? C1 C2 C3 113.2(2) . . ? C1 C2 H2A 108.9 . . ? C3 C2 H2A 108.9 . . ? C1 C2 H2B 108.9 . . ? C3 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? N2 C3 C2 110.1(2) . . ? N2 C3 H3A 109.6 . . ? C2 C3 H3A 109.6 . . ? N2 C3 H3B 109.6 . . ? C2 C3 H3B 109.6 . . ? H3A C3 H3B 108.2 . . ? N2 C4 C5 113.5(2) . . ? N2 C4 H4A 108.9 . . ? C5 C4 H4A 108.9 . . ? N2 C4 H4B 108.9 . . ? C5 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? C6 C5 C4 113.2(2) . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5A 108.9 . . ? C6 C5 H5B 108.9 . . ? C4 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? N3 C6 C5 113.4(2) . . ? N3 C6 H6A 108.9 . . ? C5 C6 H6A 108.9 . . ? N3 C6 H6B 108.9 . . ? C5 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H1 F6 0.822(18) 1.617(19) 2.439(3) 177(3) . N2 H2C F5 0.90 1.76 2.661(3) 177.7 . N1 H1A F2 0.89 2.02 2.826(3) 150.0 1_655 N1 H1B F2 0.89 1.91 2.791(3) 170.5 2_655 N1 H1C F7 0.89 2.24 2.832(3) 124.1 2_655 N1 H1C F3 0.89 2.49 2.943(3) 111.8 2_655 N3 H3C F2 0.89 2.26 2.790(3) 118.1 1_556 N3 H3D F6 0.89 2.15 2.894(3) 140.9 1_546 N3 H3E F7 0.89 2.03 2.778(3) 140.6 1_546 N3 H3C O2 0.89 2.28 2.976(3) 135.1 2_556 N3 H3C F7 0.89 2.51 2.951(3) 111.0 2_556 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.399 _refine_diff_density_min -0.519 _refine_diff_density_rms 0.075 #===end