# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_VOF-1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H7 N2 F5 O2 V2' _chemical_formula_sum 'C7 H7 F5 N2 O2 V2' _chemical_formula_weight 348.03 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' 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' 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 n' _symmetry_space_group_name_Hall 'P -2yac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 7.5005(15) _cell_length_b 11.811(2) _cell_length_c 11.636(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.154(3) _cell_angle_gamma 90.00 _cell_volume 1030.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour Blue _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 1.881 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.77490 _diffrn_radiation_type synchrotron _diffrn_radiation_source '11.3.1 ALS. LBNL.CA' _diffrn_radiation_monochromator 'Si (111) Crystal' _diffrn_measurement_device_type 'Bruker AXS APEXII' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean none _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 14156 _diffrn_reflns_av_R_equivalents 0.0693 _diffrn_reflns_av_sigmaI/netI 0.0999 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.49 _diffrn_reflns_theta_max 33.76 _reflns_number_total 6092 _reflns_number_gt 3623 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEXII (Bruker, 2006)' _computing_cell_refinement 'SAINT (Bruker, 2006)' _computing_data_reduction 'SAINT (Bruker, 2006)' _computing_structure_solution 'SHELXS-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. A run of PLATON suggested possible higher symmetry; attempts to solve the structure in P2/n or P2/c was not successful due to severe desorder, also the template could not be located and the R-factors are very high. Flack parameter was 0.378 with esd 0.018 indicating possible racemic twinning. ; _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^)+(0.0365P)^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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.38(3) _refine_ls_number_reflns 6092 _refine_ls_number_parameters 326 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1104 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1029 _refine_ls_wR_factor_gt 0.0857 _refine_ls_goodness_of_fit_ref 0.939 _refine_ls_restrained_S_all 0.939 _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 F7 F 0.1089(3) 0.08306(19) 0.1667(2) 0.0139(6) Uani 1 1 d . . . F10 F 0.0996(4) -0.0839(2) -0.0108(2) 0.0217(7) Uani 1 1 d . . . F3 F 0.1719(3) -0.08222(19) 0.6681(2) 0.0150(6) Uani 1 1 d . . . F9 F 0.1776(3) -0.06223(18) 0.3114(2) 0.0142(6) Uani 1 1 d . . . F5 F 0.1780(4) 0.0834(2) 0.4907(2) 0.0231(7) Uani 1 1 d . . . F1 F 0.1102(3) 0.06298(19) 0.8109(2) 0.0143(6) Uani 1 1 d . . . F2 F -0.1063(4) -0.10292(18) 0.1758(2) 0.0177(6) Uani 1 1 d . . . F4 F 0.3874(3) -0.05251(18) 0.1226(2) 0.0174(6) Uani 1 1 d . . . F6 F 0.3899(4) 0.12118(18) 0.3044(2) 0.0159(7) Uani 1 1 d . . . O4 O 0.1775(4) -0.2318(2) 0.1675(3) 0.0205(8) Uani 1 1 d . . . F8 F -0.1107(4) 0.06974(18) 0.3550(2) 0.0177(6) Uani 1 1 d . . . O3 O 0.0989(4) 0.2479(3) 0.3290(3) 0.0206(8) Uani 1 1 d . . . O1 O 0.0995(4) 0.2317(2) 0.6642(3) 0.0173(7) Uani 1 1 d . . . O2 O 0.1789(4) -0.2477(3) -0.1714(3) 0.0228(8) Uani 1 1 d . . . C3 C 0.9327(6) 0.3881(3) 0.9483(4) 0.0185(10) Uani 1 1 d . . . C13 C 0.4390(6) 0.3616(3) 0.9482(4) 0.0171(10) Uani 1 1 d . . . C2 C 0.8631(6) 0.3604(4) 1.0534(4) 0.0180(10) Uani 1 1 d . . . C12 C 0.3604(6) 0.3286(3) 1.0511(4) 0.0138(10) Uani 1 1 d . . . C14 C 0.4731(6) 0.4752(4) 0.9222(4) 0.0216(11) Uani 1 1 d . . . H14 H 0.5270 0.4975 0.8546 0.026 Uiso 1 1 calc R . . C15 C 0.4199(6) 0.5527(4) 1.0060(5) 0.0278(13) Uani 1 1 d . . . H15 H 0.4353 0.6297 0.9927 0.033 Uiso 1 1 calc R . . C16 C 0.3451(6) 0.5182(3) 1.1081(4) 0.0236(11) Uani 1 1 d . . . H16 H 0.3153 0.5731 1.1616 0.028 Uiso 1 1 calc R . . C6 C 0.8552(6) 0.5535(4) 1.1042(5) 0.0285(12) Uani 1 1 d . . . H6 H 0.8288 0.6112 1.1555 0.034 Uiso 1 1 calc R . . C4 C 0.9685(6) 0.5010(4) 0.9169(5) 0.0267(12) Uani 1 1 d . . . H4 H 1.0173 0.5206 0.8468 0.032 Uiso 1 1 calc R . . C5 C 0.9248(6) 0.5804(4) 0.9992(5) 0.0283(13) Uani 1 1 d . . . H5 H 0.9435 0.6565 0.9825 0.034 Uiso 1 1 calc R . . C1 C 0.8235(6) 0.4415(4) 1.1351(4) 0.0208(10) Uani 1 1 d . . . H1 H 0.7784 0.4222 1.2064 0.025 Uiso 1 1 calc R . . C11 C 0.3129(6) 0.4074(4) 1.1338(4) 0.0213(10) Uani 1 1 d . . . H11 H 0.2622 0.3858 1.2027 0.026 Uiso 1 1 calc R . . N12 N 0.3459(5) 0.2123(3) 1.0448(3) 0.0181(9) Uani 1 1 d . . . H12 H 0.3008 0.1699 1.0968 0.022 Uiso 1 1 calc R . . N2 N 0.8498(5) 0.2440(3) 1.0542(3) 0.0168(8) Uani 1 1 d . . . H2 H 0.8099 0.2043 1.1101 0.020 Uiso 1 1 calc R . . C17 C 0.4109(6) 0.1757(3) 0.9477(4) 0.0207(11) Uani 1 1 d . . . H17 H 0.4168 0.1002 0.9253 0.025 Uiso 1 1 calc R . . C7 C 0.9072(6) 0.2028(4) 0.9569(4) 0.0212(11) Uani 1 1 d . . . H7 H 0.9101 0.1265 0.9373 0.025 Uiso 1 1 calc R . . N1 N 0.9607(5) 0.2878(3) 0.8907(4) 0.0231(10) Uani 1 1 d . . . H1A H 1.0052 0.2812 0.8235 0.028 Uiso 1 1 calc R . . N11 N 0.4670(5) 0.2631(3) 0.8863(3) 0.0189(9) Uani 1 1 d . . . H11A H 0.5131 0.2592 0.8193 0.023 Uiso 1 1 calc R . . V1 V 0.13692(9) 0.09944(5) 0.64953(7) 0.01353(17) Uani 1 1 d . . . V2 V 0.14213(11) -0.11535(5) -0.16710(8) 0.01563(19) Uani 1 1 d . . . V3 V 0.13138(10) 0.11588(6) 0.33259(7) 0.01555(18) Uani 1 1 d . . . V4 V 0.14965(10) -0.09870(5) 0.14994(7) 0.01425(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F7 0.0162(13) 0.0142(10) 0.0114(13) -0.0014(9) -0.0006(10) -0.0018(9) F10 0.0233(15) 0.0268(13) 0.0147(14) -0.0002(11) -0.0046(12) -0.0004(11) F3 0.0149(13) 0.0135(11) 0.0163(14) 0.0011(9) -0.0055(10) -0.0003(9) F9 0.0189(13) 0.0100(10) 0.0135(14) 0.0000(9) -0.0021(11) 0.0031(9) F5 0.0243(16) 0.0271(13) 0.0179(16) 0.0001(12) -0.0019(13) -0.0007(12) F1 0.0176(14) 0.0135(11) 0.0118(14) 0.0009(9) 0.0038(11) 0.0021(10) F2 0.0144(12) 0.0184(11) 0.0203(16) 0.0015(10) -0.0008(12) -0.0017(10) F4 0.0086(12) 0.0212(11) 0.0224(14) 0.0007(10) -0.0025(11) 0.0006(10) F6 0.0116(13) 0.0175(11) 0.0184(16) -0.0024(9) -0.0022(12) -0.0019(9) O4 0.0307(18) 0.0091(12) 0.0215(18) 0.0002(12) -0.0027(14) 0.0007(12) F8 0.0222(14) 0.0135(10) 0.0172(14) 0.0014(9) -0.0008(12) 0.0027(10) O3 0.0125(17) 0.0183(14) 0.031(2) -0.0009(14) 0.0015(15) 0.0007(12) O1 0.0191(16) 0.0119(13) 0.0206(17) 0.0005(12) -0.0059(13) 0.0008(11) O2 0.0216(19) 0.0134(13) 0.033(2) 0.0039(14) -0.0005(16) 0.0048(12) C3 0.010(2) 0.020(2) 0.025(2) 0.0005(18) -0.0052(17) 0.0007(16) C13 0.015(2) 0.0152(18) 0.021(2) -0.0021(17) -0.0050(17) 0.0036(15) C2 0.026(2) 0.0159(19) 0.012(2) 0.0020(17) 0.0007(19) 0.0028(18) C12 0.016(2) 0.0125(18) 0.013(2) 0.0021(16) -0.0007(17) 0.0023(16) C14 0.021(2) 0.022(2) 0.022(3) 0.0086(18) 0.002(2) -0.0037(17) C15 0.034(3) 0.016(2) 0.033(3) 0.004(2) -0.011(2) 0.0043(19) C16 0.025(2) 0.015(2) 0.030(3) -0.0044(18) -0.005(2) 0.0049(17) C6 0.025(2) 0.021(2) 0.039(3) -0.010(2) -0.004(2) 0.0053(19) C4 0.019(2) 0.029(2) 0.033(3) 0.011(2) -0.003(2) -0.0039(19) C5 0.028(3) 0.020(2) 0.036(3) 0.007(2) -0.012(3) -0.0021(17) C1 0.020(2) 0.019(2) 0.023(2) 0.0001(18) 0.0001(19) 0.0025(17) C11 0.022(2) 0.021(2) 0.020(2) -0.0035(19) 0.0013(19) 0.0018(18) N12 0.023(2) 0.0129(16) 0.019(2) 0.0013(14) 0.0007(16) -0.0060(14) N2 0.0194(18) 0.0147(16) 0.0162(19) 0.0012(14) 0.0012(15) -0.0009(14) C17 0.023(2) 0.0138(19) 0.025(3) -0.0067(18) -0.001(2) 0.0024(17) C7 0.017(2) 0.022(2) 0.024(3) -0.0082(18) 0.001(2) -0.0012(18) N1 0.023(2) 0.032(2) 0.015(2) -0.0078(17) 0.0037(16) -0.0060(17) N11 0.025(2) 0.0181(17) 0.0140(19) -0.0003(15) 0.0031(15) -0.0007(15) V1 0.0143(4) 0.0106(3) 0.0156(4) 0.0002(3) -0.0016(3) 0.0013(3) V2 0.0161(4) 0.0115(3) 0.0193(4) 0.0018(3) -0.0012(3) 0.0000(3) V3 0.0177(4) 0.0123(3) 0.0166(4) -0.0023(3) -0.0004(3) 0.0012(3) V4 0.0189(4) 0.0102(3) 0.0135(4) -0.0014(3) -0.0015(3) 0.0026(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F7 V3 1.972(3) . ? F7 V4 2.178(2) . ? F10 V2 1.889(3) . ? F10 V4 1.909(3) . ? F3 V2 1.974(3) 1_556 ? F3 V1 2.172(2) . ? F9 V4 1.935(3) . ? F9 V3 2.147(2) . ? F5 V1 1.889(3) . ? F5 V3 1.905(3) . ? F1 V1 1.941(3) . ? F1 V2 2.135(2) 1_556 ? F2 V1 1.944(3) 2_454 ? F2 V4 1.950(3) . ? F4 V4 1.898(3) . ? F4 V1 1.971(2) 2_554 ? F6 V2 1.915(3) 2 ? F6 V3 1.974(3) . ? O4 V4 1.599(3) . ? F8 V3 1.918(3) . ? F8 V2 1.943(3) 2_455 ? O3 V3 1.578(3) . ? O1 V1 1.597(3) . ? O2 V2 1.589(3) . ? C3 C2 1.378(6) . ? C3 N1 1.380(6) . ? C3 C4 1.410(6) . ? C13 N11 1.387(5) . ? C13 C14 1.400(6) . ? C13 C12 1.400(6) . ? C2 N2 1.379(5) . ? C2 C1 1.386(6) . ? C12 N12 1.381(5) . ? C12 C11 1.390(6) . ? C14 C15 1.401(7) . ? C15 C16 1.385(7) . ? C16 C11 1.365(6) . ? C6 C5 1.375(8) . ? C6 C1 1.393(6) . ? C4 C5 1.384(7) . ? N12 C17 1.312(5) . ? N2 C7 1.313(5) . ? C17 N11 1.329(6) . ? C7 N1 1.332(6) . ? V1 F2 1.944(3) 2 ? V1 F4 1.971(2) 2_455 ? V2 F6 1.915(3) 2_454 ? V2 F8 1.943(3) 2_554 ? V2 F3 1.974(3) 1_554 ? V2 F1 2.135(2) 1_554 ? 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 V3 F7 V4 105.79(11) . . ? V2 F10 V4 153.09(16) . . ? V2 F3 V1 106.07(11) 1_556 . ? V4 F9 V3 108.37(11) . . ? V1 F5 V3 153.43(17) . . ? V1 F1 V2 108.75(12) . 1_556 ? V1 F2 V4 161.88(15) 2_454 . ? V4 F4 V1 141.71(13) . 2_554 ? V2 F6 V3 160.08(15) 2 . ? V3 F8 V2 143.75(13) . 2_455 ? C2 C3 N1 106.9(4) . . ? C2 C3 C4 122.1(4) . . ? N1 C3 C4 130.9(5) . . ? N11 C13 C14 131.4(4) . . ? N11 C13 C12 106.3(4) . . ? C14 C13 C12 122.3(4) . . ? C3 C2 N2 105.8(4) . . ? C3 C2 C1 122.4(4) . . ? N2 C2 C1 131.9(4) . . ? N12 C12 C11 133.0(4) . . ? N12 C12 C13 105.4(4) . . ? C11 C12 C13 121.6(4) . . ? C13 C14 C15 114.8(4) . . ? C16 C15 C14 122.1(4) . . ? C11 C16 C15 123.1(4) . . ? C5 C6 C1 121.3(5) . . ? C5 C4 C3 114.4(5) . . ? C6 C5 C4 123.8(4) . . ? C2 C1 C6 116.0(5) . . ? C16 C11 C12 116.2(4) . . ? C17 N12 C12 110.1(4) . . ? C7 N2 C2 109.8(4) . . ? N12 C17 N11 109.5(4) . . ? N2 C7 N1 109.1(4) . . ? C7 N1 C3 108.4(4) . . ? C17 N11 C13 108.6(4) . . ? O1 V1 F5 103.60(15) . . ? O1 V1 F1 95.26(14) . . ? F5 V1 F1 161.14(11) . . ? O1 V1 F2 97.94(13) . 2 ? F5 V1 F2 88.59(12) . 2 ? F1 V1 F2 88.51(11) . 2 ? O1 V1 F4 97.11(13) . 2_455 ? F5 V1 F4 89.39(12) . 2_455 ? F1 V1 F4 88.57(11) . 2_455 ? F2 V1 F4 164.87(10) 2 2_455 ? O1 V1 F3 167.64(14) . . ? F5 V1 F3 88.68(11) . . ? F1 V1 F3 72.48(9) . . ? F2 V1 F3 83.56(9) 2 . ? F4 V1 F3 81.40(9) 2_455 . ? O2 V2 F10 104.87(16) . . ? O2 V2 F6 97.51(14) . 2_454 ? F10 V2 F6 89.33(12) . 2_454 ? O2 V2 F8 96.38(14) . 2_554 ? F10 V2 F8 89.85(12) . 2_554 ? F6 V2 F8 165.81(10) 2_454 2_554 ? O2 V2 F3 98.12(15) . 1_554 ? F10 V2 F3 157.00(11) . 1_554 ? F6 V2 F3 88.26(11) 2_454 1_554 ? F8 V2 F3 86.97(11) 2_554 1_554 ? O2 V2 F1 170.55(16) . 1_554 ? F10 V2 F1 84.31(11) . 1_554 ? F6 V2 F1 84.64(10) 2_454 1_554 ? F8 V2 F1 81.19(10) 2_554 1_554 ? F3 V2 F1 72.69(9) 1_554 1_554 ? O3 V3 F5 104.46(15) . . ? O3 V3 F8 97.94(14) . . ? F5 V3 F8 88.14(12) . . ? O3 V3 F7 99.09(14) . . ? F5 V3 F7 156.35(11) . . ? F8 V3 F7 90.84(11) . . ? O3 V3 F6 96.66(13) . . ? F5 V3 F6 90.29(12) . . ? F8 V3 F6 165.25(10) . . ? F7 V3 F6 84.75(11) . . ? O3 V3 F9 171.85(15) . . ? F5 V3 F9 83.51(11) . . ? F8 V3 F9 83.84(10) . . ? F7 V3 F9 72.89(9) . . ? F6 V3 F9 81.41(10) . . ? O4 V4 F4 100.56(14) . . ? O4 V4 F10 103.74(14) . . ? F4 V4 F10 88.64(12) . . ? O4 V4 F9 94.80(14) . . ? F4 V4 F9 90.87(11) . . ? F10 V4 F9 161.22(11) . . ? O4 V4 F2 94.69(14) . . ? F4 V4 F2 164.71(10) . . ? F10 V4 F2 88.78(12) . . ? F9 V4 F2 86.77(11) . . ? O4 V4 F7 167.50(14) . . ? F4 V4 F7 82.28(10) . . ? F10 V4 F7 88.44(10) . . ? F9 V4 F7 72.91(9) . . ? F2 V4 F7 82.59(9) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 33.76 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.489 _refine_diff_density_min -0.739 _refine_diff_density_rms 0.121 _database_code_depnum_ccdc_archive 'CCDC 957929' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_VOF-2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H5 N2, F5 O2 V2' _chemical_formula_sum 'C4 H5 F5 N2 O2 V2' _chemical_formula_weight 309.98 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 orthorhombic _symmetry_space_group_name_H-M 'P c m n' _symmetry_space_group_name_Hall '-P 2n 2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y, z-1/2' 'x, -y-1/2, z' _cell_length_a 7.551(3) _cell_length_b 11.904(5) _cell_length_c 19.349(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1739.2(12) _cell_formula_units_Z 8 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 3934 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 28.4 _exptl_crystal_description Platelet _exptl_crystal_colour Blue _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 2.213 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.662 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _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 _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 10499 _diffrn_reflns_av_R_equivalents 0.1207 _diffrn_reflns_av_sigmaI/netI 0.0835 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.33 _reflns_number_total 1657 _reflns_number_gt 1102 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_structure_solution 'SHELXS-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^)+(0.1589P)^2^+22.3843P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1657 _refine_ls_number_parameters 145 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1414 _refine_ls_R_factor_gt 0.0931 _refine_ls_wR_factor_ref 0.3293 _refine_ls_wR_factor_gt 0.2793 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _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 N1 N 0.1931(12) 0.2500 0.3783(7) 0.046(3) Uani 1 2 d S . . H1 H 0.1662 0.2500 0.3352 0.055 Uiso 1 2 calc SR . . N12 N -0.2178(14) 0.2500 0.4950(7) 0.052(3) Uani 1 2 d S . . C11 C -0.2877(9) 0.1539(6) 0.3963(4) 0.0272(19) Uani 1 1 d . . . H11 H -0.3061 0.0862 0.3734 0.033 Uiso 1 1 calc R . . N11 N -0.3102(14) 0.2500 0.3613(6) 0.052(3) Uani 1 2 d S . . H11A H -0.3379 0.2500 0.3182 0.062 Uiso 1 2 calc SR . . C1 C 0.2138(11) 0.1535(8) 0.4115(5) 0.046(3) Uani 1 1 d . . . H1A H 0.1955 0.0857 0.3887 0.056 Uiso 1 1 calc R . . N2 N 0.2810(17) 0.2500 0.5100(7) 0.143(12) Uani 1 2 d SD . . C12 C -0.2406(10) 0.1516(7) 0.4619(4) 0.031(2) Uani 1 1 d . . . H12 H -0.2234 0.0837 0.4847 0.037 Uiso 1 1 calc R . . C2 C 0.2608(16) 0.1549(10) 0.4775(6) 0.106(4) Uani 1 1 d D . . H2 H 0.2794 0.0876 0.5008 0.127 Uiso 1 1 calc R . . V1 V -0.04971(16) 0.09438(10) 0.18922(6) 0.0196(4) Uani 1 1 d . . . V2 V -0.03634(16) -0.09484(10) 0.31181(6) 0.0188(4) Uani 1 1 d . . . F1 F -0.0849(8) -0.2500 0.2905(4) 0.0282(16) Uani 1 2 d S . . F2 F -0.0783(5) -0.0653(3) 0.2039(2) 0.0218(10) Uani 1 1 d . . . F4 F 0.0030(8) 0.2500 0.2114(3) 0.0272(16) Uani 1 2 d S . . F3 F 0.2080(5) 0.0666(4) 0.1815(2) 0.0273(11) Uani 1 1 d . . . F5 F -0.2926(5) 0.1204(3) 0.2196(2) 0.0225(10) Uani 1 1 d . . . F6 F -0.0042(5) 0.0674(4) 0.2977(2) 0.0216(10) Uani 1 1 d . . . O1 O -0.0861(7) 0.0998(5) 0.1077(3) 0.0326(15) Uani 1 1 d . . . O2 O 0.0044(7) -0.0952(4) 0.3933(3) 0.0226(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.024(5) 0.050(6) 0.063(7) 0.000 -0.005(5) 0.000 N12 0.033(6) 0.046(7) 0.078(9) 0.000 0.003(6) 0.000 C11 0.021(3) 0.021(4) 0.039(4) 0.002(3) 0.004(3) -0.008(3) N11 0.039(6) 0.079(8) 0.038(6) 0.000 0.002(5) 0.000 C1 0.046(5) 0.031(5) 0.062(6) 0.004(4) 0.020(4) 0.031(4) N2 0.030(7) 0.35(4) 0.048(9) 0.000 0.014(6) 0.000 C12 0.024(3) 0.030(4) 0.040(5) 0.013(4) 0.002(3) -0.002(4) C2 0.078(6) 0.182(12) 0.058(7) 0.075(7) 0.040(5) 0.088(8) V1 0.0166(6) 0.0202(7) 0.0220(7) 0.0024(5) -0.0004(5) -0.0023(5) V2 0.0161(6) 0.0136(7) 0.0267(8) 0.0022(5) -0.0004(5) 0.0016(5) F1 0.021(3) 0.016(3) 0.048(4) 0.000 0.006(3) 0.000 F2 0.0240(19) 0.0119(18) 0.030(2) 0.0050(18) -0.0064(17) -0.0047(18) F4 0.026(3) 0.022(3) 0.033(4) 0.000 -0.003(3) 0.000 F3 0.015(2) 0.022(2) 0.045(3) 0.0048(19) 0.0052(17) 0.0069(19) F5 0.0183(19) 0.028(2) 0.022(2) 0.0033(18) -0.0064(16) 0.0021(19) F6 0.0211(18) 0.023(2) 0.021(2) -0.0005(18) -0.0011(17) 0.000(2) O1 0.024(2) 0.046(4) 0.027(3) 0.004(3) -0.001(2) 0.001(3) O2 0.028(2) 0.013(3) 0.026(3) -0.001(2) -0.002(2) -0.003(2) _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 N1 C1 1.325(11) 8_565 ? N1 C1 1.325(11) . ? N12 C12 1.346(10) . ? N12 C12 1.346(10) 8_565 ? C11 C12 1.319(11) . ? C11 N11 1.340(10) . ? N11 C11 1.340(10) 8_565 ? C1 C2 1.327(15) . ? N2 C2 1.304(12) 8_565 ? N2 C2 1.304(12) . ? V1 O1 1.602(5) . ? V1 F2 1.934(4) . ? V1 F4 1.943(2) . ? V1 F5 1.951(4) . ? V1 F3 1.979(4) . ? V1 F6 2.151(4) . ? V2 O2 1.606(5) . ? V2 F1 1.928(2) . ? V2 F5 1.962(4) 3 ? V2 F3 1.964(4) 3_455 ? V2 F6 1.966(5) . ? V2 F2 2.141(4) . ? F1 V2 1.928(2) 8 ? F4 V1 1.943(2) 8_565 ? F3 V2 1.964(4) 3 ? F5 V2 1.962(4) 3_455 ? 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 C1 N1 C1 120.3(13) 8_565 . ? C12 N12 C12 120.9(12) . 8_565 ? C12 C11 N11 122.5(8) . . ? C11 N11 C11 117.3(11) 8_565 . ? N1 C1 C2 119.2(10) . . ? C2 N2 C2 120.6(15) 8_565 . ? C11 C12 N12 118.4(8) . . ? N2 C2 C1 120.4(12) . . ? O1 V1 F2 99.5(2) . . ? O1 V1 F4 102.3(3) . . ? F2 V1 F4 158.1(2) . . ? O1 V1 F5 97.4(2) . . ? F2 V1 F5 90.38(18) . . ? F4 V1 F5 88.6(2) . . ? O1 V1 F3 95.8(2) . . ? F2 V1 F3 87.53(18) . . ? F4 V1 F3 88.5(2) . . ? F5 V1 F3 166.77(18) . . ? O1 V1 F6 173.7(2) . . ? F2 V1 F6 74.22(17) . . ? F4 V1 F6 83.9(2) . . ? F5 V1 F6 83.10(16) . . ? F3 V1 F6 83.76(17) . . ? O2 V2 F1 104.1(3) . . ? O2 V2 F5 97.1(2) . 3 ? F1 V2 F5 87.9(2) . 3 ? O2 V2 F3 97.1(2) . 3_455 ? F1 V2 F3 89.5(2) . 3_455 ? F5 V2 F3 165.70(18) 3 3_455 ? O2 V2 F6 96.6(2) . . ? F1 V2 F6 159.3(2) . . ? F5 V2 F6 89.62(17) 3 . ? F3 V2 F6 87.85(18) 3_455 . ? O2 V2 F2 170.4(2) . . ? F1 V2 F2 85.5(2) . . ? F5 V2 F2 82.08(16) 3 . ? F3 V2 F2 83.69(17) 3_455 . ? F6 V2 F2 73.82(16) . . ? V2 F1 V2 146.7(4) 8 . ? V1 F2 V2 106.75(19) . . ? V1 F4 V1 145.0(4) . 8_565 ? V2 F3 V1 158.9(3) 3 . ? V1 F5 V2 139.8(2) . 3_455 ? V2 F6 V1 105.20(19) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.219 _refine_diff_density_min -1.746 _refine_diff_density_rms 0.306 _database_code_depnum_ccdc_archive 'CCDC 957930' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_VOF-3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C3 H5 N2, F5 O2 V2' _chemical_formula_sum 'C3 H5 F5 N2 O2 V2' _chemical_formula_weight 297.97 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' 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' 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' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.170(3) _cell_length_b 17.333(7) _cell_length_c 7.370(4) _cell_angle_alpha 90.00 _cell_angle_beta 118.0531(10) _cell_angle_gamma 90.00 _cell_volume 808.32(6) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 2767 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 28.2 _exptl_crystal_description Platele _exptl_crystal_colour Blue _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 2.375 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _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 _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 4961 _diffrn_reflns_av_R_equivalents 0.0509 _diffrn_reflns_av_sigmaI/netI 0.0691 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 25.34 _reflns_number_total 2153 _reflns_number_gt 1875 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Flack parameter was 0.490 with esd 0.06 which indicates the structure is possibly twinned ; _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^)+(0.0256P)^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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.49(6) _refine_ls_number_reflns 2153 _refine_ls_number_parameters 254 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.0815 _refine_ls_wR_factor_gt 0.0772 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.024 _refine_ls_shift/su_mean 0.003 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 0.87399(16) 0.49965(7) 0.09431(17) 0.0123(3) Uani 1 1 d . . . V2 V 1.08408(16) 0.40263(7) -0.14415(17) 0.0111(3) Uani 1 1 d . . . V3 V 0.35494(16) 0.49889(7) -0.41867(17) 0.0116(3) Uani 1 1 d . . . V4 V 0.60029(16) 0.40462(7) 0.36893(17) 0.0114(3) Uani 1 1 d . . . F5 F 0.8926(5) 0.3923(2) -0.0273(5) 0.0133(8) Uani 1 1 d . . . F6 F 0.6384(5) 0.5150(2) -0.1856(5) 0.0127(8) Uani 1 1 d . . . F7 F 1.3209(5) 0.3889(3) 0.1310(5) 0.0156(9) Uani 1 1 d . . . F8 F 1.1006(5) 0.4582(3) 0.3503(5) 0.0143(9) Uani 1 1 d . . . F10 F 0.6794(5) 0.4545(3) 0.1788(6) 0.0194(9) Uani 1 1 d . . . O1 O 0.8836(6) 0.5875(3) 0.1624(7) 0.0162(12) Uani 1 1 d . . . F12 F 0.2793(5) 0.4472(3) -0.2274(6) 0.0190(9) Uani 1 1 d . . . F13 F 1.0696(5) 0.5130(2) -0.0239(5) 0.0132(8) Uani 1 1 d . . . F11 F 0.8577(5) 0.4450(3) -0.3968(5) 0.0146(9) Uani 1 1 d . . . O17 O 1.0752(7) 0.3153(3) -0.2197(7) 0.0174(12) Uani 1 1 d . . . O18 O 0.6856(7) 0.3190(3) 0.3843(7) 0.0197(12) Uani 1 1 d . . . C19 N 0.6822(9) 0.1439(4) 0.8874(11) 0.0255(17) Uani 1 1 d . . . H19 H 0.7229 0.0967 0.8987 0.031 Uiso 1 1 calc R . . N20 N 0.1968(9) 0.1414(4) 0.3170(10) 0.0257(16) Uani 1 1 d . . . H20 H 0.2317 0.0979 0.2856 0.031 Uiso 1 1 calc R . . C21 C 0.1517(11) 0.1526(5) 0.4657(13) 0.031(2) Uani 1 1 d . . . H21 H 0.1539 0.1151 0.5567 0.037 Uiso 1 1 calc R . . C22 N 0.6074(9) 0.2589(4) 0.7818(10) 0.0192(15) Uani 1 1 d . . . H22 H 0.5898 0.3002 0.7107 0.023 Uiso 1 1 calc R . . N23 C 0.6750(9) 0.1931(6) 0.7492(12) 0.0259(19) Uani 1 1 d . . . H23 H 0.7116 0.1830 0.6461 0.031 Uiso 1 1 calc R . . N24 N 0.1032(9) 0.2245(4) 0.4674(10) 0.0308(19) Uani 1 1 d . . . H24 H 0.0676 0.2452 0.5526 0.037 Uiso 1 1 calc R . . C11 C 0.1805(9) 0.2093(6) 0.2181(11) 0.029(2) Uani 1 1 d . . . H11 H 0.2077 0.2172 0.1079 0.035 Uiso 1 1 calc R . . C26 C 0.5695(10) 0.2526(5) 0.9434(11) 0.0224(19) Uani 1 1 d . . . H26 H 0.5212 0.2915 0.9979 0.027 Uiso 1 1 calc R . . N11 C 0.6142(11) 0.1800(4) 1.0109(12) 0.026(2) Uani 1 1 d . . . H11A H 0.6017 0.1583 1.1200 0.032 Uiso 1 1 calc R . . C28 C 0.1182(11) 0.2624(5) 0.3092(14) 0.029(2) Uani 1 1 d . . . H28 H 0.0905 0.3142 0.2738 0.035 Uiso 1 1 calc R . . F31 F 0.4788(5) 0.5136(2) -0.6020(5) 0.0126(8) Uani 1 1 d . . . O4 O 0.2724(7) 0.5846(3) -0.4217(8) 0.0174(12) Uani 1 1 d . . . F41 F 0.4771(5) 0.3892(2) 0.5560(5) 0.0134(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 V1 0.0125(5) 0.0158(7) 0.0093(6) 0.0000(6) 0.0057(5) 0.0005(5) V2 0.0113(5) 0.0129(7) 0.0095(6) -0.0002(6) 0.0053(5) 0.0009(5) V3 0.0125(6) 0.0144(7) 0.0090(6) -0.0010(6) 0.0058(5) 0.0009(5) V4 0.0123(6) 0.0140(7) 0.0086(6) 0.0001(5) 0.0053(5) 0.0008(5) F5 0.0183(18) 0.013(2) 0.012(2) -0.0010(17) 0.0095(16) -0.0003(16) F6 0.0113(18) 0.016(2) 0.011(2) -0.0033(18) 0.0052(15) -0.0050(15) F7 0.0132(18) 0.021(2) 0.012(2) 0.0009(18) 0.0053(15) 0.0014(16) F8 0.015(2) 0.018(2) 0.011(2) -0.0008(17) 0.0073(17) -0.0003(16) F10 0.0161(19) 0.031(2) 0.013(2) 0.0026(19) 0.0080(16) -0.0007(17) O1 0.012(2) 0.021(3) 0.012(3) -0.002(2) 0.003(2) 0.002(2) F12 0.0100(18) 0.033(2) 0.016(2) -0.003(2) 0.0073(16) -0.0030(17) F13 0.0111(18) 0.017(2) 0.014(2) -0.0004(18) 0.0081(15) -0.0024(15) F11 0.0111(19) 0.023(2) 0.008(2) 0.0005(17) 0.0032(16) 0.0004(16) O17 0.017(2) 0.018(3) 0.015(3) -0.004(2) 0.005(2) 0.002(2) O18 0.020(3) 0.015(3) 0.019(3) -0.005(2) 0.006(2) 0.003(2) C19 0.024(3) 0.014(4) 0.040(5) 0.007(3) 0.016(3) 0.006(3) N20 0.026(3) 0.023(4) 0.025(4) -0.004(3) 0.009(3) 0.006(3) C21 0.026(4) 0.039(6) 0.014(5) 0.008(4) -0.002(4) -0.012(4) C22 0.019(3) 0.017(4) 0.014(3) 0.006(3) 0.003(3) 0.002(3) N23 0.024(4) 0.036(5) 0.021(5) -0.009(4) 0.014(4) 0.006(4) N24 0.023(3) 0.045(5) 0.025(4) -0.017(3) 0.011(3) 0.001(3) C11 0.024(4) 0.043(5) 0.026(5) -0.003(5) 0.017(4) -0.004(4) C26 0.018(4) 0.028(5) 0.015(4) -0.008(4) 0.003(3) 0.003(3) N11 0.019(4) 0.031(6) 0.024(5) 0.018(4) 0.006(4) 0.004(3) C28 0.024(4) 0.015(5) 0.034(5) 0.006(4) 0.001(4) 0.004(3) F31 0.0149(19) 0.014(2) 0.012(2) -0.0006(17) 0.0084(15) -0.0003(15) O4 0.019(2) 0.019(3) 0.016(3) -0.001(2) 0.010(2) 0.005(2) F41 0.0157(18) 0.012(2) 0.014(2) 0.0015(17) 0.0084(15) 0.0005(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 1.595(6) . ? V1 F10 1.940(4) . ? V1 F8 1.958(4) . ? V1 F6 1.975(3) . ? V1 F13 1.982(3) . ? V1 F5 2.097(4) . ? V2 O17 1.603(5) . ? V2 F12 1.934(4) 1_655 ? V2 F5 1.942(3) . ? V2 F11 1.949(4) . ? V2 F7 1.953(4) . ? V2 F13 2.131(4) . ? V3 O4 1.596(5) . ? V3 F12 1.950(4) . ? V3 F8 1.950(4) 1_454 ? V3 F31 1.951(4) . ? V3 F6 1.969(3) . ? V3 F41 2.138(4) 1_554 ? V4 O18 1.588(5) . ? V4 F10 1.944(4) . ? V4 F7 1.964(3) 1_455 ? V4 F11 1.970(4) 1_556 ? V4 F41 1.975(4) . ? V4 F31 2.133(4) 1_556 ? F7 V4 1.964(3) 1_655 ? F8 V3 1.950(4) 1_656 ? F12 V2 1.934(4) 1_455 ? F11 V4 1.970(4) 1_554 ? C19 N23 1.311(11) . ? C19 N11 1.368(11) . ? N20 C21 1.295(11) . ? N20 C11 1.359(11) . ? C21 N24 1.294(10) . ? C22 N23 1.305(11) . ? C22 C26 1.345(11) . ? N24 C28 1.386(12) . ? C11 C28 1.334(12) . ? C26 N11 1.336(10) . ? F31 V4 2.133(4) 1_554 ? F41 V3 2.138(4) 1_556 ? 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 F10 102.5(2) . . ? O1 V1 F8 98.9(2) . . ? F10 V1 F8 86.47(16) . . ? O1 V1 F6 95.1(2) . . ? F10 V1 F6 89.93(15) . . ? F8 V1 F6 166.0(2) . . ? O1 V1 F13 95.3(2) . . ? F10 V1 F13 162.2(2) . . ? F8 V1 F13 91.62(14) . . ? F6 V1 F13 87.68(14) . . ? O1 V1 F5 168.5(2) . . ? F10 V1 F5 88.78(17) . . ? F8 V1 F5 83.99(17) . . ? F6 V1 F5 82.43(15) . . ? F13 V1 F5 73.46(14) . . ? O17 V2 F12 100.6(2) . 1_655 ? O17 V2 F5 98.4(2) . . ? F12 V2 F5 161.0(2) 1_655 . ? O17 V2 F11 98.3(2) . . ? F12 V2 F11 87.02(16) 1_655 . ? F5 V2 F11 90.79(14) . . ? O17 V2 F7 96.8(2) . . ? F12 V2 F7 88.41(15) 1_655 . ? F5 V2 F7 88.81(15) . . ? F11 V2 F7 164.7(2) . . ? O17 V2 F13 171.8(2) . . ? F12 V2 F13 87.54(17) 1_655 . ? F5 V2 F13 73.50(15) . . ? F11 V2 F13 82.95(17) . . ? F7 V2 F13 82.30(15) . . ? O4 V3 F12 102.1(2) . . ? O4 V3 F8 97.8(2) . 1_454 ? F12 V3 F8 90.08(17) . 1_454 ? O4 V3 F31 98.9(2) . . ? F12 V3 F31 158.8(2) . . ? F8 V3 F31 89.20(14) 1_454 . ? O4 V3 F6 96.0(2) . . ? F12 V3 F6 87.60(15) . . ? F8 V3 F6 166.2(2) 1_454 . ? F31 V3 F6 88.07(14) . . ? O4 V3 F41 172.5(2) . 1_554 ? F12 V3 F41 85.37(18) . 1_554 ? F8 V3 F41 81.68(17) 1_454 1_554 ? F31 V3 F41 73.59(15) . 1_554 ? F6 V3 F41 84.55(15) . 1_554 ? O18 V4 F10 103.5(3) . . ? O18 V4 F7 97.5(2) . 1_455 ? F10 V4 F7 86.50(16) . 1_455 ? O18 V4 F11 95.7(2) . 1_556 ? F10 V4 F11 90.17(17) . 1_556 ? F7 V4 F11 166.8(2) 1_455 1_556 ? O18 V4 F41 96.2(2) . . ? F10 V4 F41 160.3(2) . . ? F7 V4 F41 90.08(15) 1_455 . ? F11 V4 F41 88.77(15) 1_556 . ? O18 V4 F31 169.1(2) . 1_556 ? F10 V4 F31 87.14(18) . 1_556 ? F7 V4 F31 85.37(15) 1_455 1_556 ? F11 V4 F31 81.69(17) 1_556 1_556 ? F41 V4 F31 73.25(15) . 1_556 ? V2 F5 V1 107.92(19) . . ? V3 F6 V1 156.5(2) . . ? V2 F7 V4 159.1(3) . 1_655 ? V3 F8 V1 136.1(3) 1_656 . ? V1 F10 V4 155.3(2) . . ? V2 F12 V3 154.37(19) 1_455 . ? V1 F13 V2 105.12(18) . . ? V2 F11 V4 136.0(3) . 1_554 ? N23 C19 N11 108.9(7) . . ? C21 N20 C11 109.4(7) . . ? N24 C21 N20 109.1(8) . . ? N23 C22 C26 109.8(7) . . ? C22 N23 C19 107.9(6) . . ? C21 N24 C28 108.7(8) . . ? C28 C11 N20 106.9(7) . . ? N11 C26 C22 107.0(7) . . ? C26 N11 C19 106.3(8) . . ? C11 C28 N24 105.9(8) . . ? V3 F31 V4 107.09(19) . 1_554 ? V4 F41 V3 106.06(19) . 1_556 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.522 _refine_diff_density_min -0.504 _refine_diff_density_rms 0.117 _database_code_depnum_ccdc_archive 'CCDC 957931' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_VOF-4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H4 F4 N2 O2 V2' _chemical_formula_weight 289.97 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' 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' 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' _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 5.0096(14) _cell_length_b 10.8260(3) _cell_length_c 7.288(7) _cell_angle_alpha 90.00 _cell_angle_beta 95.9430(10) _cell_angle_gamma 90.00 _cell_volume 393.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 1103 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 25.4 _exptl_crystal_description Platelet _exptl_crystal_colour Blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 2.421 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.648 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _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 _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 2184 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 25.35 _reflns_number_total 710 _reflns_number_gt 612 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_structure_solution 'SHELXS-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^)+(0.0178P)^2^+0.6673P] 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 NONE _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 710 _refine_ls_number_parameters 72 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0337 _refine_ls_R_factor_gt 0.0262 _refine_ls_wR_factor_ref 0.0565 _refine_ls_wR_factor_gt 0.0540 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 H2 H 0.439(6) 0.187(3) 0.362(4) 0.014(8) Uiso 1 1 d . . . H1 H 0.778(6) -0.140(3) 0.378(4) 0.019(8) Uiso 1 1 d . . . V1 V 0.77782(10) 0.06583(4) 0.08918(7) 0.01105(16) Uani 1 1 d . . . F1 F 1.0852(3) -0.04258(13) 0.1536(2) 0.0135(4) Uani 1 1 d . . . N1 N 0.6225(5) 0.0279(2) 0.3432(3) 0.0116(5) Uani 1 1 d . . . F2 F 0.5774(3) -0.10779(13) 0.0210(2) 0.0129(4) Uani 1 1 d . . . O1 O 0.8886(4) 0.19806(17) 0.1522(3) 0.0184(5) Uani 1 1 d . . . C2 C 0.4607(6) 0.1091(3) 0.4159(4) 0.0132(6) Uani 1 1 d . . . C1 C 0.6622(6) -0.0816(3) 0.4294(4) 0.0148(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 V1 0.0098(3) 0.0116(3) 0.0119(3) -0.0003(2) 0.00176(19) -0.00135(19) F1 0.0118(9) 0.0176(9) 0.0115(9) 0.0018(7) 0.0027(7) 0.0003(6) N1 0.0084(13) 0.0135(12) 0.0127(14) -0.0015(10) -0.0009(10) -0.0006(9) F2 0.0113(9) 0.0115(8) 0.0159(10) 0.0007(6) 0.0016(7) -0.0001(6) O1 0.0188(12) 0.0160(10) 0.0207(12) -0.0011(9) 0.0043(9) -0.0035(8) C2 0.0148(16) 0.0118(15) 0.0124(17) -0.0016(12) -0.0007(13) 0.0007(11) C1 0.0142(16) 0.0142(15) 0.0157(17) -0.0016(12) -0.0005(13) 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 O1 1.5861(19) . ? V1 F2 1.9291(17) 3_655 ? V1 F1 1.9544(16) . ? V1 F1 1.979(2) 3_755 ? V1 N1 2.121(3) . ? V1 F2 2.1645(15) . ? V1 V1 3.0456(12) 3_755 ? F1 V1 1.979(2) 3_755 ? N1 C2 1.342(4) . ? N1 C1 1.346(4) . ? F2 V1 1.9291(17) 3_655 ? C2 C1 1.372(4) 3_656 ? C1 C2 1.372(4) 3_656 ? 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 F2 100.83(9) . 3_655 ? O1 V1 F1 103.25(9) . . ? F2 V1 F1 155.69(7) 3_655 . ? O1 V1 F1 103.34(9) . 3_755 ? F2 V1 F1 92.76(8) 3_655 3_755 ? F1 V1 F1 78.51(8) . 3_755 ? O1 V1 N1 94.06(10) . . ? F2 V1 N1 90.17(9) 3_655 . ? F1 V1 N1 91.44(8) . . ? F1 V1 N1 161.47(8) 3_755 . ? O1 V1 F2 172.05(9) . . ? F2 V1 F2 73.91(7) 3_655 . ? F1 V1 F2 82.47(6) . . ? F1 V1 F2 83.09(6) 3_755 . ? N1 V1 F2 80.15(8) . . ? O1 V1 V1 107.27(8) . 3_755 ? F2 V1 V1 128.03(7) 3_655 3_755 ? F1 V1 V1 39.55(6) . 3_755 ? F1 V1 V1 38.97(5) 3_755 3_755 ? N1 V1 V1 129.21(7) . 3_755 ? F2 V1 V1 80.66(5) . 3_755 ? V1 F1 V1 101.49(8) . 3_755 ? C2 N1 C1 117.3(3) . . ? C2 N1 V1 120.59(19) . . ? C1 N1 V1 121.9(2) . . ? V1 F2 V1 106.08(7) 3_655 . ? N1 C2 C1 121.5(3) . 3_656 ? N1 C1 C2 121.2(3) . 3_656 ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.318 _refine_diff_density_min -0.368 _refine_diff_density_rms 0.082 _database_code_depnum_ccdc_archive 'CCDC 957932' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_VOF-5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(F3 O V), C3 H5 N2, H4 N' _chemical_formula_sum 'C3 H9 F6 N3 O2 V2' _chemical_formula_weight 335.01 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 ? _symmetry_space_group_name_H-M 'P 2 2 21' _symmetry_space_group_name_Hall 'P 2c 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, -z' '-x, y, -z+1/2' _cell_length_a 3.861(3) _cell_length_b 6.664(4) _cell_length_c 19.840(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 510.5(5) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 2031 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 2808 _exptl_crystal_description Platelet _exptl_crystal_colour Blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.179 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 1.950 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.584 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _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 _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 3262 _diffrn_reflns_av_R_equivalents 0.0665 _diffrn_reflns_av_sigmaI/netI 0.0623 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.33 _reflns_number_total 940 _reflns_number_gt 892 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_structure_solution 'SHELXS-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^)+(0.0368P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(4) _refine_ls_number_reflns 940 _refine_ls_number_parameters 92 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.0836 _refine_ls_wR_factor_gt 0.0825 _refine_ls_goodness_of_fit_ref 1.165 _refine_ls_restrained_S_all 1.164 _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 0.0451(2) 0.06763(10) 0.08019(3) 0.0090(2) Uani 1 1 d . . . F1 F -0.4573(7) 0.0888(3) 0.06734(10) 0.0135(5) Uani 1 1 d . . . F3 F 0.0429(6) 0.3529(3) 0.09649(9) 0.0120(5) Uani 1 1 d . . . F2 F 0.0372(6) -0.1748(3) 0.02545(9) 0.0102(5) Uani 1 1 d . . . O1 O 0.0434(8) -0.0151(4) 0.15513(13) 0.0152(7) Uani 1 1 d . . . N1 N 0.6492(10) 0.4278(6) 0.20469(16) 0.0162(8) Uani 1 1 d D . . C2 C 0.5000 0.3136(9) 0.2500 0.0188(14) Uani 1 2 d S . . N2 N 0.5307(15) 0.5000 0.0000 0.0121(10) Uani 1 2 d S . . C1 C 0.5938(16) 0.6244(7) 0.2215(3) 0.0296(13) Uani 1 1 d . . . H13 H 0.682(14) 0.597(9) 0.010(3) 0.049(19) Uiso 1 1 d . . . H14 H 0.355(14) 0.523(9) -0.040(3) 0.055(18) Uiso 1 1 d . . . H1 H 0.668(14) 0.720(9) 0.195(2) 0.047(17) Uiso 1 1 d . . . H2 H 0.772(10) 0.389(7) 0.1712(16) 0.021(13) Uiso 1 1 d D . . H3 H 0.5000 0.195(10) 0.2500 0.024(19) Uiso 1 2 d S . . 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 0.0096(4) 0.0076(4) 0.0098(3) -0.0002(2) 0.0001(3) 0.0000(3) F1 0.0046(12) 0.0173(12) 0.0186(11) -0.0021(9) -0.0004(9) -0.0001(11) F3 0.0128(13) 0.0081(11) 0.0149(10) -0.0009(8) 0.0016(9) 0.0012(11) F2 0.0112(13) 0.0067(10) 0.0129(10) 0.0003(8) -0.0011(9) -0.0006(12) O1 0.0154(17) 0.0139(14) 0.0164(13) 0.0012(11) 0.0001(13) -0.0013(15) N1 0.014(2) 0.021(2) 0.0131(17) 0.0027(17) 0.0025(14) 0.0011(18) C2 0.027(4) 0.007(3) 0.022(3) 0.000 -0.005(3) 0.000 N2 0.007(3) 0.011(2) 0.019(2) 0.001(2) 0.000 0.000 C1 0.038(4) 0.010(2) 0.041(3) 0.006(2) 0.020(3) 0.002(2) _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 1.586(3) . ? V1 F3 1.929(2) . ? V1 F1 1.943(3) 1_655 ? V1 F2 1.947(2) . ? V1 F1 1.961(3) . ? V1 F2 2.214(2) 3 ? F1 V1 1.943(3) 1_455 ? F2 V1 2.214(2) 3 ? N1 C2 1.311(5) . ? N1 C1 1.369(6) . ? C2 N1 1.311(5) 4_655 ? C1 C1 1.342(9) 4_655 ? 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 100.69(12) . . ? O1 V1 F1 98.76(13) . 1_655 ? F3 V1 F1 87.41(10) . 1_655 ? O1 V1 F2 103.56(12) . . ? F3 V1 F2 155.72(9) . . ? F1 V1 F2 90.15(10) 1_655 . ? O1 V1 F1 98.20(13) . . ? F3 V1 F1 86.94(10) . . ? F1 V1 F1 162.84(12) 1_655 . ? F2 V1 F1 88.38(9) . . ? O1 V1 F2 178.16(12) . 3 ? F3 V1 F2 80.83(8) . 3 ? F1 V1 F2 82.30(9) 1_655 3 ? F2 V1 F2 74.91(9) . 3 ? F1 V1 F2 80.81(9) . 3 ? V1 F1 V1 162.84(12) 1_455 . ? V1 F2 V1 105.07(9) . 3 ? C2 N1 C1 108.6(4) . . ? N1 C2 N1 109.0(6) 4_655 . ? C1 C1 N1 106.8(2) 4_655 . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.33 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.722 _refine_diff_density_min -0.757 _refine_diff_density_rms 0.207 _database_code_depnum_ccdc_archive 'CCDC 957933' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_VOF-6 # start Validation Reply Form _vrf_PLAT213_VOF-6 ; PROBLEM: Atom C2 has ADP max/min Ratio ..... 11.8 prola RESPONSE: Unresolved disorder ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'F6 K O2 V2, C3 H5 N2' _chemical_formula_sum 'C3 H5 F6 K N2 O2 V2' _chemical_formula_weight 356.07 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' K K 0.2009 0.2494 '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 orthorhombic _symmetry_space_group_name_H-M 'P 2 2 21' _symmetry_space_group_name_Hall 'P 2c 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, -z' '-x, y, -z+1/2' _cell_length_a 3.8572(13) _cell_length_b 6.4795(2) _cell_length_c 20.0510(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 501.13(17) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 3553 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 28.8 _exptl_crystal_description NEEDLE _exptl_crystal_colour Blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 2.355 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.732 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _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 _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 3145 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0362 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 25.30 _reflns_number_total 906 _reflns_number_gt 868 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0822P)^2^+2.7862P] 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 NONE _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.63(15) _refine_ls_number_reflns 906 _refine_ls_number_parameters 74 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1746 _refine_ls_wR_factor_gt 0.1421 _refine_ls_goodness_of_fit_ref 1.263 _refine_ls_restrained_S_all 1.263 _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 0.5157(4) 0.42324(18) 0.07840(6) 0.0161(4) Uani 1 1 d . . . K1 K 0.0077(8) 0.0000 0.0000 0.0245(6) Uani 1 2 d S . . F2 F 0.0149(14) 0.4012(7) 0.0650(2) 0.0227(10) Uani 1 1 d . . . F3 F 0.5128(16) 0.1303(6) 0.0918(2) 0.0207(10) Uani 1 1 d . . . F1 F 0.5157(14) 0.6765(6) 0.0270(2) 0.0187(9) Uani 1 1 d . . . O1 O 0.5156(19) 0.4998(8) 0.1535(3) 0.0234(12) Uani 1 1 d . . . C1 C 0.0000 0.1732(17) 0.2500 0.026(2) Uani 1 2 d S . . H31 H 0.0000 0.3167 0.2500 0.031 Uiso 1 2 calc SR . . N1 N 0.134(2) 0.0634(13) 0.2029(4) 0.033(2) Uani 1 1 d . . . H2 H 0.2347 0.1060 0.1672 0.040 Uiso 1 1 calc R . . C2 C 0.079(6) -0.1383(18) 0.2228(14) 0.194(18) Uani 1 1 d . . . H3 H 0.1497 -0.2552 0.1995 0.232 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 0.0121(7) 0.0154(7) 0.0209(7) -0.0027(4) 0.0000(6) 0.0005(8) K1 0.0215(13) 0.0240(12) 0.0280(12) -0.0028(9) 0.000 0.000 F2 0.014(2) 0.026(2) 0.028(2) -0.0018(17) 0.001(2) 0.002(3) F3 0.022(2) 0.020(2) 0.021(2) -0.0012(17) -0.001(2) 0.002(3) F1 0.015(2) 0.017(2) 0.024(2) -0.0031(16) -0.002(2) -0.002(3) O1 0.023(3) 0.022(3) 0.025(3) -0.007(2) -0.001(3) 0.001(4) C1 0.027(6) 0.018(5) 0.034(6) 0.000 0.010(7) 0.000 N1 0.041(5) 0.030(4) 0.028(4) -0.011(4) 0.012(3) -0.009(4) C2 0.22(2) 0.018(6) 0.35(4) -0.034(11) 0.27(3) -0.034(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag V1 O1 1.586(5) . ? V1 F3 1.917(4) . ? V1 F1 1.937(4) . ? V1 F2 1.949(6) 1_655 ? V1 F2 1.955(6) . ? V1 F1 2.211(4) 3_565 ? V1 K1 3.687(2) 1_655 ? V1 K1 3.719(2) . ? K1 F3 2.783(6) 3_455 ? K1 F3 2.783(6) 1_455 ? K1 F3 2.810(6) . ? K1 F3 2.810(6) 3 ? K1 F1 2.879(5) 1_445 ? K1 F1 2.879(5) 3_465 ? K1 F2 2.909(4) . ? K1 F2 2.909(4) 3 ? K1 F1 2.920(5) 1_545 ? K1 F1 2.920(5) 3_565 ? K1 V1 3.687(2) 3_455 ? K1 V1 3.687(2) 1_455 ? F2 V1 1.949(6) 1_455 ? F3 K1 2.783(6) 1_655 ? F1 V1 2.211(4) 3_565 ? F1 K1 2.879(5) 1_665 ? F1 K1 2.920(5) 1_565 ? C1 N1 1.290(10) . ? C1 N1 1.290(10) 4 ? N1 C2 1.383(16) . ? C2 C2 1.25(3) 4 ? 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 100.2(2) . . ? O1 V1 F1 103.9(2) . . ? F3 V1 F1 155.93(18) . . ? O1 V1 F2 98.8(3) . 1_655 ? F3 V1 F2 87.3(2) . 1_655 ? F1 V1 F2 89.4(2) . 1_655 ? O1 V1 F2 98.8(3) . . ? F3 V1 F2 86.6(2) . . ? F1 V1 F2 89.4(2) . . ? F2 V1 F2 162.1(3) 1_655 . ? O1 V1 F1 178.8(2) . 3_565 ? F3 V1 F1 81.06(16) . 3_565 ? F1 V1 F1 74.87(17) . 3_565 ? F2 V1 F1 81.21(19) 1_655 3_565 ? F2 V1 F1 81.2(2) . 3_565 ? O1 V1 K1 129.6(2) . 1_655 ? F3 V1 K1 47.64(16) . 1_655 ? F1 V1 K1 113.78(14) . 1_655 ? F2 V1 K1 51.58(13) 1_655 1_655 ? F2 V1 K1 113.31(14) . 1_655 ? F1 V1 K1 51.30(12) 3_565 1_655 ? O1 V1 K1 129.2(2) . . ? F3 V1 K1 47.63(16) . . ? F1 V1 K1 113.57(14) . . ? F2 V1 K1 114.10(14) 1_655 . ? F2 V1 K1 50.79(14) . . ? F1 V1 K1 51.70(13) 3_565 . ? K1 V1 K1 62.77(3) 1_655 . ? F3 K1 F3 93.4(2) 3_455 1_455 ? F3 K1 F3 179.4(2) 3_455 . ? F3 K1 F3 87.21(11) 1_455 . ? F3 K1 F3 87.21(11) 3_455 3 ? F3 K1 F3 179.4(2) 1_455 3 ? F3 K1 F3 92.2(2) . 3 ? F3 K1 F1 56.74(13) 3_455 1_445 ? F3 K1 F1 69.16(15) 1_455 1_445 ? F3 K1 F1 123.53(12) . 1_445 ? F3 K1 F1 111.20(12) 3 1_445 ? F3 K1 F1 69.16(15) 3_455 3_465 ? F3 K1 F1 56.74(13) 1_455 3_465 ? F3 K1 F1 111.20(12) . 3_465 ? F3 K1 F1 123.53(12) 3 3_465 ? F1 K1 F1 97.5(2) 1_445 3_465 ? F3 K1 F2 125.05(16) 3_455 . ? F3 K1 F2 55.87(13) 1_455 . ? F3 K1 F2 55.33(14) . . ? F3 K1 F2 123.74(15) 3 . ? F1 K1 F2 124.94(15) 1_445 . ? F1 K1 F2 55.94(13) 3_465 . ? F3 K1 F2 55.87(13) 3_455 3 ? F3 K1 F2 125.05(16) 1_455 3 ? F3 K1 F2 123.75(15) . 3 ? F3 K1 F2 55.33(14) 3 3 ? F1 K1 F2 55.94(13) 1_445 3 ? F1 K1 F2 124.94(15) 3_465 3 ? F2 K1 F2 178.9(2) . 3 ? F3 K1 F1 111.43(13) 3_455 1_545 ? F3 K1 F1 123.73(12) 1_455 1_545 ? F3 K1 F1 68.21(14) . 1_545 ? F3 K1 F1 55.99(14) 3 1_545 ? F1 K1 F1 83.38(11) 1_445 1_545 ? F1 K1 F1 179.09(19) 3_465 1_545 ? F2 K1 F1 123.50(15) . 1_545 ? F2 K1 F1 55.61(12) 3 1_545 ? F3 K1 F1 123.73(12) 3_455 3_565 ? F3 K1 F1 111.43(13) 1_455 3_565 ? F3 K1 F1 55.99(14) . 3_565 ? F3 K1 F1 68.21(14) 3 3_565 ? F1 K1 F1 179.09(19) 1_445 3_565 ? F1 K1 F1 83.38(11) 3_465 3_565 ? F2 K1 F1 55.61(12) . 3_565 ? F2 K1 F1 123.50(15) 3 3_565 ? F1 K1 F1 95.7(2) 1_545 3_565 ? F3 K1 V1 30.61(9) 3_455 3_455 ? F3 K1 V1 98.89(13) 1_455 3_455 ? F3 K1 V1 149.27(9) . 3_455 ? F3 K1 V1 81.62(11) 3 3_455 ? F1 K1 V1 36.82(8) 1_445 3_455 ? F1 K1 V1 97.01(12) 3_465 3_455 ? F2 K1 V1 149.42(14) . 3_455 ? F2 K1 V1 31.67(11) 3 3_455 ? F1 K1 V1 83.72(9) 1_545 3_455 ? F1 K1 V1 143.15(8) 3_565 3_455 ? F3 K1 V1 98.89(13) 3_455 1_455 ? F3 K1 V1 30.61(9) 1_455 1_455 ? F3 K1 V1 81.62(11) . 1_455 ? F3 K1 V1 149.27(9) 3 1_455 ? F1 K1 V1 97.01(12) 1_445 1_455 ? F1 K1 V1 36.82(8) 3_465 1_455 ? F2 K1 V1 31.67(11) . 1_455 ? F2 K1 V1 149.42(14) 3 1_455 ? F1 K1 V1 143.15(8) 1_545 1_455 ? F1 K1 V1 83.72(9) 3_565 1_455 ? V1 K1 V1 118.04(10) 3_455 1_455 ? V1 F2 V1 162.1(3) 1_455 . ? V1 F2 K1 96.75(18) 1_455 . ? V1 F2 K1 97.82(19) . . ? V1 F3 K1 101.8(2) . 1_655 ? V1 F3 K1 102.1(2) . . ? K1 F3 K1 87.21(11) 1_655 . ? V1 F1 V1 105.13(17) . 3_565 ? V1 F1 K1 135.8(2) . 1_665 ? V1 F1 K1 91.88(15) 3_565 1_665 ? V1 F1 K1 135.0(2) . 1_565 ? V1 F1 K1 91.85(15) 3_565 1_565 ? K1 F1 K1 83.38(11) 1_665 1_565 ? N1 C1 N1 113.0(11) . 4 ? C1 N1 C2 104.4(9) . . ? C2 C2 N1 109.0(7) 4 . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.30 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.071 _refine_diff_density_min -1.058 _refine_diff_density_rms 0.277 _database_code_depnum_ccdc_archive 'CCDC 957934' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_VOF-7 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C2 H8 N, F3 O V' _chemical_formula_sum 'C2 H8 F3 N O V' _chemical_formula_weight 170.03 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' 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' 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 orthorhombic _symmetry_space_group_name_H-M 'P m c b' _symmetry_space_group_name_Hall '-P 2bc 2' 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' '-x, -y, -z' 'x, y-1/2, -z-1/2' '-x, y, z' 'x, -y-1/2, z-1/2' _cell_length_a 3.828(2) _cell_length_b 7.496(4) _cell_length_c 19.2021(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 551.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 812 _cell_measurement_theta_min 8.2 _cell_measurement_theta_max 27.4 __exptl_crystal_description Platelet _exptl_crystal_colour Blue _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.050 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 1.767 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.888 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _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 _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 2171 _diffrn_reflns_av_R_equivalents 0.0571 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 8.25 _diffrn_reflns_theta_max 27.72 _reflns_number_total 598 _reflns_number_gt 462 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_structure_solution 'SHELXS-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^)+(0.0397P)^2^+9.4531P] 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 NONE _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 598 _refine_ls_number_parameters 52 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1114 _refine_ls_R_factor_gt 0.0839 _refine_ls_wR_factor_ref 0.1737 _refine_ls_wR_factor_gt 0.1612 _refine_ls_goodness_of_fit_ref 1.150 _refine_ls_restrained_S_all 1.150 _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 C2 C 0.0000 -0.1349(14) 0.1599(5) 0.040(2) Uani 1 2 d S . . C1 C 0.0000 0.009(2) 0.2028(9) 0.077(5) Uani 1 2 d S . . H1A H 0.0000 -0.0304 0.2504 0.116 Uiso 1 2 calc SR . . H1B H -0.2048 0.0796 0.1942 0.116 Uiso 0.50 1 calc PR . . H1C H 0.2048 0.0796 0.1942 0.116 Uiso 0.50 1 calc PR . . N1 N 0.0000 -0.1263(16) 0.0844(4) 0.066(3) Uani 1 2 d S . . H1D H 0.0000 -0.2364 0.0670 0.099 Uiso 1 2 calc SR . . H1E H 0.1898 -0.0686 0.0700 0.099 Uiso 0.50 1 calc PR . . H1F H -0.1898 -0.0686 0.0700 0.099 Uiso 0.50 1 calc PR . . F3B F 0.0000 0.3238(10) 0.0469(4) 0.0143(17) Uiso 0.50 2 d SP . . F3A F 0.0000 0.4097(10) 0.0672(4) 0.0150(18) Uani 0.50 2 d SP . . V1 V 0.5000 0.37104(14) 0.07179(6) 0.0101(2) Uani 1 2 d S . . F1 F 0.5000 0.6228(6) 0.0421(2) 0.0282(11) Uani 1 2 d S . . O1 O 0.5000 0.3946(7) 0.1528(3) 0.0363(17) Uani 1 2 d S . . F2 F 0.5000 0.1222(6) 0.0595(2) 0.0522(19) Uani 1 2 d S . . 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 C2 0.017(4) 0.048(5) 0.054(5) 0.026(5) 0.000 0.000 C1 0.064(9) 0.064(8) 0.104(11) -0.004(8) 0.000 0.000 N1 0.008(3) 0.141(7) 0.050(5) -0.068(5) 0.000 0.000 F3A 0.008(3) 0.016(4) 0.021(4) 0.003(3) 0.000 0.000 V1 0.0070(5) 0.0080(5) 0.0154(5) 0.0000(5) 0.000 0.000 F1 0.056(3) 0.0068(17) 0.0219(19) 0.0009(18) 0.000 0.000 O1 0.072(5) 0.018(3) 0.019(3) 0.000(2) 0.000 0.000 F2 0.120(5) 0.0096(19) 0.027(3) -0.0011(19) 0.000 0.000 _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 C2 C1 1.358(19) . ? C2 N1 1.450(13) . ? F3B F3A 0.754(10) . ? F3B V1 2.005(3) . ? F3B V1 2.005(3) 1_455 ? F3A V1 1.9378(16) . ? F3A V1 1.9378(16) 1_455 ? V1 O1 1.566(6) . ? V1 F2 1.880(5) . ? V1 F3A 1.9378(16) 1_655 ? V1 F1 1.971(4) . ? V1 F3B 2.005(3) 1_655 ? V1 F1 2.188(5) 5_665 ? F1 V1 2.188(5) 5_665 ? 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 C1 C2 N1 124.8(11) . . ? F3A F3B V1 74.0(2) . . ? F3A F3B V1 74.0(2) . 1_455 ? V1 F3B V1 145.4(4) . 1_455 ? F3B F3A V1 84.0(2) . . ? F3B F3A V1 84.0(2) . 1_455 ? V1 F3A V1 162.0(4) . 1_455 ? O1 V1 F2 103.7(2) . . ? O1 V1 F3A 91.6(3) . 1_655 ? F2 V1 F3A 98.2(2) . 1_655 ? O1 V1 F3A 91.6(3) . . ? F2 V1 F3A 98.2(2) . . ? F3A V1 F3A 162.0(4) 1_655 . ? O1 V1 F1 100.3(2) . . ? F2 V1 F1 156.0(2) . . ? F3A V1 F1 81.0(2) 1_655 . ? F3A V1 F1 81.0(2) . . ? O1 V1 F3B 104.9(2) . 1_655 ? F2 V1 F3B 78.1(2) . 1_655 ? F3A V1 F3B 22.0(3) 1_655 1_655 ? F3A V1 F3B 163.5(3) . 1_655 ? F1 V1 F3B 95.8(2) . 1_655 ? O1 V1 F3B 104.9(2) . . ? F2 V1 F3B 78.1(2) . . ? F3A V1 F3B 163.5(3) 1_655 . ? F3A V1 F3B 22.0(3) . . ? F1 V1 F3B 95.8(2) . . ? F3B V1 F3B 145.4(4) 1_655 . ? O1 V1 F1 172.3(2) . 5_665 ? F2 V1 F1 84.00(18) . 5_665 ? F3A V1 F1 87.2(3) 1_655 5_665 ? F3A V1 F1 87.2(3) . 5_665 ? F1 V1 F1 72.01(19) . 5_665 ? F3B V1 F1 76.4(2) 1_655 5_665 ? F3B V1 F1 76.4(2) . 5_665 ? V1 F1 V1 107.99(19) . 5_665 ? _diffrn_measured_fraction_theta_max 0.815 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 2.404 _refine_diff_density_min -0.734 _refine_diff_density_rms 0.171 _database_code_depnum_ccdc_archive 'CCDC 957935' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_VOF-8 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'F3 O V, C7 H7 N2' _chemical_formula_sum 'C7 H7 F3 N2 O V' _chemical_formula_weight 243.09 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' 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' 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.5014(10) _cell_length_b 3.8344(13) _cell_length_c 18.979(7) _cell_angle_alpha 90.00 _cell_angle_beta 105.454(7) _cell_angle_gamma 90.00 _cell_volume 1718.6(9) _cell_formula_units_Z 8 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 2848 _cell_measurement_theta_min 1.7 _cell_measurement_theta_max 26.4 _exptl_crystal_description Platelet _exptl_crystal_colour Blue _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.879 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 1.169 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.765 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _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 _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 6591 _diffrn_reflns_av_R_equivalents 0.0628 _diffrn_reflns_av_sigmaI/netI 0.0499 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 26.39 _reflns_number_total 1745 _reflns_number_gt 1529 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_structure_solution 'SHELXS-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^)+(0.1591P)^2^+1.2554P] 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 NONE _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1745 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0874 _refine_ls_R_factor_gt 0.0618 _refine_ls_wR_factor_ref 0.2644 _refine_ls_wR_factor_gt 0.2080 _refine_ls_goodness_of_fit_ref 1.276 _refine_ls_restrained_S_all 1.276 _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 F2 F 0.46416(6) 0.0025(3) 0.78427(8) 0.0286(4) Uani 1 1 d . . . F3 F 0.45536(11) 0.5057(3) 0.67894(11) 0.0550(6) Uani 1 1 d . . . O1 O 0.37560(9) 0.0035(5) 0.66253(12) 0.0429(7) Uani 1 1 d . . . H1 H 0.6924(13) -0.122(9) 0.7314(16) 0.047(8) Uiso 1 1 d . . . H2 H 0.5728(10) -0.336(8) 0.6721(14) 0.036(7) Uiso 1 1 d . . . H3 H 0.5747(10) -0.738(7) 0.4870(13) 0.034(7) Uiso 1 1 d . . . H4 H 0.6884(9) -0.591(6) 0.4913(12) 0.012(5) Uiso 1 1 d . . . H5 H 0.5198(12) -0.653(9) 0.5754(16) 0.048(8) Uiso 1 1 d . . . H6 H 0.7749(10) -0.127(7) 0.6888(12) 0.023(6) Uiso 1 1 d . . . H7 H 0.7686(10) -0.378(6) 0.5692(13) 0.020(6) Uiso 1 1 d . . . V1 V 0.441920(15) 0.00691(8) 0.677316(19) 0.01909(12) Uani 1 1 d . . . F1 F 0.45325(7) 0.0055(3) 0.58107(8) 0.0344(4) Uani 1 1 d . . . N1 N 0.58780(8) -0.6438(5) 0.53598(10) 0.0247(5) Uani 1 1 d . . . N2 N 0.58650(8) -0.4030(6) 0.63959(10) 0.0280(5) Uani 1 1 d . . . C2 C 0.55624(10) -0.5747(7) 0.58095(13) 0.0260(6) Uani 1 1 d . . . C7 C 0.68901(10) -0.2090(6) 0.67878(12) 0.0307(6) Uani 1 1 d . . . C1 C 0.64061(9) -0.3590(6) 0.63244(11) 0.0247(5) Uani 1 1 d . . . C6 C 0.73750(11) -0.2200(7) 0.65461(14) 0.0352(7) Uani 1 1 d . . . C5 C 0.73797(10) -0.3673(7) 0.58766(14) 0.0330(6) Uani 1 1 d . . . C3 C 0.64166(11) -0.5098(5) 0.56604(14) 0.0239(6) Uani 1 1 d . . . C4 C 0.69059(11) -0.5179(6) 0.54179(15) 0.0288(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F2 0.0213(6) 0.0442(9) 0.0214(6) 0.0012(5) 0.0077(5) 0.0014(5) F3 0.0721(12) 0.0105(8) 0.0539(12) -0.0019(6) -0.0332(9) 0.0009(6) O1 0.0238(9) 0.0653(15) 0.0362(10) -0.0053(8) 0.0023(8) 0.0000(7) V1 0.0192(2) 0.0162(2) 0.0204(2) 0.00018(12) 0.00270(17) 0.00029(11) F1 0.0377(8) 0.0435(9) 0.0196(6) -0.0042(5) 0.0037(6) -0.0119(5) N1 0.0262(9) 0.0212(9) 0.0235(8) 0.0002(7) 0.0007(7) 0.0001(7) N2 0.0307(9) 0.0253(9) 0.0297(9) -0.0036(8) 0.0108(7) 0.0009(8) C2 0.0284(11) 0.0219(10) 0.0241(10) 0.0049(9) 0.0009(9) 0.0021(9) C7 0.0340(12) 0.0254(11) 0.0274(11) 0.0033(9) -0.0010(10) -0.0019(10) C1 0.0294(10) 0.0196(10) 0.0261(9) -0.0012(9) 0.0091(8) 0.0026(9) C6 0.0309(12) 0.0256(12) 0.0408(13) 0.0040(11) -0.0046(10) -0.0057(10) C5 0.0261(10) 0.0307(12) 0.0423(12) 0.0101(11) 0.0093(9) 0.0004(10) C3 0.0237(11) 0.0231(12) 0.0232(11) 0.0024(8) 0.0031(9) 0.0007(7) C4 0.0264(12) 0.0284(13) 0.0329(12) 0.0029(8) 0.0103(10) 0.0053(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F2 V1 1.9566(16) . ? F2 V1 2.2211(15) 2_656 ? F3 V1 1.9397(14) . ? F3 V1 1.9486(14) 1_565 ? O1 V1 1.574(2) . ? V1 F1 1.9193(18) . ? V1 F3 1.9486(14) 1_545 ? V1 F2 2.2210(15) 2_656 ? N1 C2 1.322(3) . ? N1 C3 1.389(3) . ? N1 H3 0.97(2) . ? N2 C2 1.335(3) . ? N2 C1 1.379(3) . ? N2 H2 0.82(3) . ? C2 H5 0.92(3) . ? C7 C6 1.384(4) . ? C7 C1 1.398(3) . ? C7 H1 1.04(3) . ? C1 C3 1.393(3) . ? C6 C5 1.393(4) . ? C6 H6 1.03(2) . ? C5 C4 1.379(3) . ? C5 H7 0.91(3) . ? C3 C4 1.394(4) . ? C4 H4 0.98(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag V1 F2 V1 108.56(7) . 2_656 ? V1 F3 V1 160.90(15) . 1_565 ? O1 V1 F1 103.56(10) . . ? O1 V1 F3 100.01(10) . . ? F1 V1 F3 87.19(8) . . ? O1 V1 F3 99.02(10) . 1_545 ? F1 V1 F3 86.88(8) . 1_545 ? F3 V1 F3 160.90(15) . 1_545 ? O1 V1 F2 100.01(9) . . ? F1 V1 F2 156.41(7) . . ? F3 V1 F2 89.59(7) . . ? F3 V1 F2 88.62(7) 1_545 . ? O1 V1 F2 171.41(9) . 2_656 ? F1 V1 F2 84.98(7) . 2_656 ? F3 V1 F2 81.12(8) . 2_656 ? F3 V1 F2 80.29(8) 1_545 2_656 ? F2 V1 F2 71.44(7) . 2_656 ? C2 N1 C3 108.4(2) . . ? C2 N1 H3 126.3(15) . . ? C3 N1 H3 124.7(16) . . ? C2 N2 C1 108.3(2) . . ? C2 N2 H2 122.2(18) . . ? C1 N2 H2 129.5(18) . . ? N1 C2 N2 110.3(2) . . ? N1 C2 H5 125(2) . . ? N2 C2 H5 124(2) . . ? C6 C7 C1 116.0(2) . . ? C6 C7 H1 118.3(17) . . ? C1 C7 H1 125.2(17) . . ? N2 C1 C3 106.76(19) . . ? N2 C1 C7 131.7(2) . . ? C3 C1 C7 121.5(2) . . ? C7 C6 C5 122.1(2) . . ? C7 C6 H6 118.5(14) . . ? C5 C6 H6 119.4(14) . . ? C4 C5 C6 122.4(3) . . ? C4 C5 H7 112.3(14) . . ? C6 C5 H7 125.3(14) . . ? N1 C3 C1 106.3(2) . . ? N1 C3 C4 131.5(2) . . ? C1 C3 C4 122.2(2) . . ? C5 C4 C3 115.8(2) . . ? C5 C4 H4 123.5(14) . . ? C3 C4 H4 119.8(13) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.261 _refine_diff_density_min -1.225 _refine_diff_density_rms 0.353 _database_code_depnum_ccdc_archive 'CCDC 957936' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_VOF-9 # start Validation Reply Form _vrf_PLAT241_VOF-9 ; PROBLEM: Check High Ueq as Compared to Neighbors for N1 RESPONSE: Unresolved disorder. ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H7 N2, F6 O2 V2' _chemical_formula_sum 'C4 H7 F6 N2 O2 V2' _chemical_formula_weight 329.99 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' 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' 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/m' _symmetry_space_group_name_Hall '-P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 8.334(7) _cell_length_b 7.430(6) _cell_length_c 8.998(8) _cell_angle_alpha 90.00 _cell_angle_beta 114.750(2) _cell_angle_gamma 90.00 _cell_volume 506.0(7) _cell_formula_units_Z 2 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 1970 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 26.4 _exptl_crystal_description Platelet _exptl_crystal_colour Blue _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.166 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 1.922 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.537 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _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 _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 4112 _diffrn_reflns_av_R_equivalents 0.0639 _diffrn_reflns_av_sigmaI/netI 0.0532 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 26.36 _reflns_number_total 1102 _reflns_number_gt 1005 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_structure_solution 'SHELXS-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. There is severe disorder on the 2-methylimidazolium moiety, disordered C atoms were refined isotropically ; _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^)+(0.0775P)^2^+4.7775P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens none _refine_ls_hydrogen_treatment none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1102 _refine_ls_number_parameters 73 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0884 _refine_ls_R_factor_gt 0.0803 _refine_ls_wR_factor_ref 0.2078 _refine_ls_wR_factor_gt 0.1937 _refine_ls_goodness_of_fit_ref 1.180 _refine_ls_restrained_S_all 1.180 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 1.0202(10) 0.7500 1.1401(10) 0.087(2) Uiso 1 2 d S . . N2 N 1.0113(10) 0.7500 0.9072(9) 0.087(2) Uiso 1 2 d S . . C1A C 0.9398(12) 0.7500 0.9991(11) 0.024(2) Uiso 0.50 2 d SP . . C1B C 1.0844(14) 0.7500 1.0434(13) 0.033(2) Uiso 0.50 2 d SP . . C2 C 1.2439(14) 0.7500 1.0481(13) 0.096(3) Uiso 1 2 d S . . C3 C 0.7752(15) 0.7500 0.9945(14) 0.101(3) Uiso 1 2 d S . . C4A C 1.242(2) 0.7500 1.164(2) 0.077(5) Uiso 0.50 2 d SP . . C4B C 0.777(3) 0.7500 0.881(3) 0.091(6) Uiso 0.50 2 d SP . . V1 V 0.21680(6) 0.99458(7) 0.59824(6) 0.01820(15) Uani 1 1 d . . . F1 F 0.2042(3) 0.7500 0.5062(3) 0.0230(7) Uani 1 2 d S . . F2 F -0.0050(2) 1.0478(3) 0.36456(19) 0.0196(5) Uani 1 1 d . . . F3 F 0.1848(3) 1.2500 0.6317(3) 0.0189(6) Uani 1 2 d S . . F4 F 0.3539(2) 1.0732(3) 0.4738(3) 0.0339(6) Uani 1 1 d . . . O1 O 0.3694(3) 0.9558(4) 0.7718(3) 0.0304(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 V1 0.0158(2) 0.0170(3) 0.0226(2) 0.00174(19) 0.00877(18) -0.00010(19) F1 0.0258(11) 0.0186(12) 0.0278(11) 0.000 0.0144(9) 0.000 F2 0.0196(7) 0.0214(9) 0.0188(7) 0.0030(7) 0.0090(6) 0.0005(7) F3 0.0212(10) 0.0163(12) 0.0233(10) 0.000 0.0134(8) 0.000 F4 0.0332(8) 0.0287(10) 0.0505(10) 0.0018(9) 0.0279(7) 0.0025(9) O1 0.0244(11) 0.0240(12) 0.0330(12) 0.0002(11) 0.0022(9) 0.0018(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1A 1.161(12) . ? N1 C1B 1.198(16) . ? N1 C4A 1.77(2) . ? N1 C3 1.910(13) . ? N2 C1B 1.117(13) . ? N2 C1A 1.205(15) . ? N2 C2 1.819(12) . ? N2 C4B 1.86(2) . ? C1A C1B 1.100(15) . ? C1A C4B 1.33(2) . ? C1A C3 1.355(16) . ? C1B C4A 1.308(19) . ? C1B C2 1.312(17) . ? C2 C4A 1.05(2) . ? C3 C4B 1.03(3) . ? V1 O1 1.574(2) . ? V1 F2 1.955(2) 3_576 ? V1 F3 1.9572(17) . ? V1 F1 1.9815(18) . ? V1 F4 1.993(3) . ? V1 F2 2.177(2) . ? F1 V1 1.9815(18) 4_575 ? F2 V1 1.955(2) 3_576 ? F3 V1 1.9572(17) 4_585 ? 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 C1A N1 C1B 55.6(8) . . ? C1A N1 C4A 103.3(10) . . ? C1B N1 C4A 47.7(8) . . ? C1A N1 C3 44.6(7) . . ? C1B N1 C3 100.1(8) . . ? C4A N1 C3 147.9(9) . . ? C1B N2 C1A 56.4(9) . . ? C1B N2 C2 45.8(8) . . ? C1A N2 C2 102.2(7) . . ? C1B N2 C4B 101.6(11) . . ? C1A N2 C4B 45.3(8) . . ? C2 N2 C4B 147.4(10) . . ? C1B C1A N1 63.9(9) . . ? C1B C1A N2 57.8(9) . . ? N1 C1A N2 121.7(10) . . ? C1B C1A C4B 152.4(16) . . ? N1 C1A C4B 143.7(16) . . ? N2 C1A C4B 94.6(13) . . ? C1B C1A C3 162.4(12) . . ? N1 C1A C3 98.5(10) . . ? N2 C1A C3 139.8(9) . . ? C4B C1A C3 45.2(12) . . ? C1A C1B N2 65.8(9) . . ? C1A C1B N1 60.5(9) . . ? N2 C1B N1 126.3(11) . . ? C1A C1B C4A 150.1(16) . . ? N2 C1B C4A 144.0(16) . . ? N1 C1B C4A 89.6(13) . . ? C1A C1B C2 162.5(13) . . ? N2 C1B C2 96.6(11) . . ? N1 C1B C2 137.0(10) . . ? C4A C1B C2 47.4(11) . . ? C4A C2 C1B 66.1(13) . . ? C4A C2 N2 103.7(14) . . ? C1B C2 N2 37.6(6) . . ? C4B C3 C1A 66.0(14) . . ? C4B C3 N1 102.9(15) . . ? C1A C3 N1 36.9(5) . . ? C2 C4A C1B 66.5(12) . . ? C2 C4A N1 109.1(13) . . ? C1B C4A N1 42.6(9) . . ? C3 C4B C1A 68.8(13) . . ? C3 C4B N2 108.9(15) . . ? C1A C4B N2 40.1(8) . . ? O1 V1 F2 102.29(14) . 3_576 ? O1 V1 F3 97.47(12) . . ? F2 V1 F3 86.49(10) 3_576 . ? O1 V1 F1 97.26(12) . . ? F2 V1 F1 91.74(11) 3_576 . ? F3 V1 F1 165.20(9) . . ? O1 V1 F4 101.32(14) . . ? F2 V1 F4 156.14(7) 3_576 . ? F3 V1 F4 87.10(11) . . ? F1 V1 F4 88.65(12) . . ? O1 V1 F2 176.70(13) . . ? F2 V1 F2 74.46(10) 3_576 . ? F3 V1 F2 81.80(9) . . ? F1 V1 F2 83.57(9) . . ? F4 V1 F2 81.88(10) . . ? V1 F1 V1 133.01(16) . 4_575 ? V1 F2 V1 105.54(10) 3_576 . ? V1 F3 V1 151.68(17) . 4_585 ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.469 _refine_diff_density_min -1.150 _refine_diff_density_rms 0.193 _database_code_depnum_ccdc_archive 'CCDC 957937' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_VOF-13 # start Validation Reply Form _vrf_PLAT213_VOF-13 ; PROBLEM: Atom F8 has ADP max/min Ratio ..... 12.9 prola RESPONSE: unresolved disorder ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C2 H10 N2, F6 O2 V2' _chemical_formula_sum 'C2 H10 F6 N2 O2 V2' _chemical_formula_weight 310.00 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' 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' 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/m' _symmetry_space_group_name_Hall '-P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 8.806(3) _cell_length_b 12.100(5) _cell_length_c 9.206(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.301(2) _cell_angle_gamma 90.00 _cell_volume 941.49(6) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 2744 _cell_measurement_theta_min 4.9 _cell_measurement_theta_max 27.4 _exptl_crystal_description Prism _exptl_crystal_colour Blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.187 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 2.057 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.988 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _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 _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 4340 _diffrn_reflns_av_R_equivalents 0.0601 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.91 _diffrn_reflns_theta_max 27.84 _reflns_number_total 1821 _reflns_number_gt 1711 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Disordered C atoms 'C3A, C3B' and F2 were refined isotrpically. This led to larger R-factors. ; _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^)+(0.0361P)^2^+37.1461P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1821 _refine_ls_number_parameters 125 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1180 _refine_ls_R_factor_gt 0.1123 _refine_ls_wR_factor_ref 0.2551 _refine_ls_wR_factor_gt 0.2515 _refine_ls_goodness_of_fit_ref 1.241 _refine_ls_restrained_S_all 1.241 _refine_ls_shift/su_max 0.030 _refine_ls_shift/su_mean 0.006 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 0.22200(19) 0.90984(12) 0.41060(18) 0.0149(4) Uani 1 1 d . . . V2 V 0.4115(2) 1.08551(11) 0.23630(18) 0.0148(4) Uani 1 1 d . . . F5 F 0.2510(9) 0.7500 0.3734(9) 0.0193(19) Uani 1 2 d S . . N1 N -0.3966(16) 0.7500 0.4099(13) 0.026(3) Uani 1 2 d S . . H1A H -0.4005 0.8127 0.4594 0.039 Uiso 0.50 1 calc PR . . H1B H -0.3924 0.6929 0.4719 0.039 Uiso 0.50 1 calc PR . . H1C H -0.4827 0.7444 0.3316 0.039 Uiso 0.50 1 calc PR . . F2 F 0.3892(6) 0.9235(4) 0.2625(6) 0.0160(12) Uani 1 1 d . . . F1 F 0.4346(6) 0.9039(4) 0.5598(6) 0.0189(12) Uani 1 1 d . . . F3 F 0.0559(7) 0.9092(5) 0.2186(7) 0.0303(17) Uani 1 1 d . . . F8 F 0.2113(8) 1.0835(5) 0.0775(6) 0.0284(16) Uani 1 1 d . . . O1 O 0.1198(10) 0.9047(6) 0.5311(10) 0.035(2) Uani 1 1 d . . . O2 O 0.5364(9) 1.0897(6) 0.1390(9) 0.0273(17) Uiso 1 1 d . . . F4 F 0.2508(7) 1.0678(4) 0.3822(6) 0.0213(14) Uani 1 1 d . . . C1 C -0.258(2) 0.7500 0.356(2) 0.046(5) Uani 1 2 d S . . H1D H -0.1946 0.6851 0.3946 0.056 Uiso 0.50 1 calc PR . . H1E H -0.1946 0.8149 0.3946 0.056 Uiso 0.50 1 calc PR . . N2 N -0.1633(14) 0.7500 0.1291(12) 0.017(3) Uani 1 2 d S . . H2A H -0.1971 0.7500 0.0284 0.026 Uiso 1 2 calc SR . . H2B H -0.1051 0.6899 0.1606 0.026 Uiso 0.50 1 calc PR . . H2C H -0.1051 0.8101 0.1606 0.026 Uiso 0.50 1 calc PR . . C2 C -0.301(2) 0.7500 0.191(2) 0.038(4) Uiso 1 2 d S . . H2D H -0.3646 0.8147 0.1540 0.045 Uiso 0.50 1 calc PR . . H2E H -0.3646 0.6853 0.1540 0.045 Uiso 0.50 1 calc PR . . N3 N -0.8839(10) 0.9079(6) -0.1118(13) 0.032(2) Uani 1 1 d . . . C3 C -0.929(2) 0.7986(16) -0.160(2) 0.013(3) Uiso 0.50 1 d P . . C3A C -0.835(2) 0.7899(15) -0.057(2) 0.016(4) Uiso 0.50 1 d P . . F6 F 0.3684(10) 1.2500 0.2524(9) 0.0199(17) Uiso 1 2 d S . . 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 0.0162(7) 0.0080(7) 0.0207(7) -0.0004(6) 0.0056(6) 0.0013(6) V2 0.0252(8) 0.0044(6) 0.0122(7) 0.0016(6) 0.0010(6) -0.0045(6) F5 0.017(4) 0.009(3) 0.030(4) 0.000 0.004(3) 0.000 N1 0.035(7) 0.030(6) 0.009(5) 0.000 -0.001(5) 0.000 F2 0.026(2) 0.009(2) 0.020(2) -0.0008(19) 0.016(2) 0.003(2) F1 0.020(3) 0.014(2) 0.016(3) 0.003(2) -0.006(2) -0.003(2) F3 0.018(3) 0.026(3) 0.032(3) 0.014(3) -0.019(3) -0.011(2) F8 0.044(4) 0.013(3) 0.016(3) 0.014(2) -0.012(3) -0.011(3) O1 0.050(4) 0.007(3) 0.048(5) 0.006(3) 0.016(4) 0.013(3) F4 0.036(3) 0.007(2) 0.015(3) 0.008(2) -0.003(2) -0.002(2) C1 0.041(10) 0.063(13) 0.042(10) 0.000 0.021(8) 0.000 N2 0.027(6) 0.013(5) 0.013(5) 0.000 0.008(5) 0.000 N3 0.020(4) 0.010(3) 0.063(6) 0.010(4) 0.008(4) 0.008(4) _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 1.614(9) . ? V1 F3 1.953(6) . ? V1 F4 1.956(5) . ? V1 F1 1.988(5) . ? V1 F5 1.993(3) . ? V1 F2 2.277(6) . ? V2 O2 1.603(9) . ? V2 F8 1.949(6) . ? V2 F1 1.987(6) 3_676 ? V2 F2 1.992(5) . ? V2 F6 2.039(2) . ? V2 F4 2.217(7) . ? F5 V1 1.993(3) 4_575 ? N1 C1 1.44(3) . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? F1 V2 1.987(6) 3_676 ? C1 C2 1.46(3) . ? C1 H1D 0.9700 . ? C1 H1E 0.9700 . ? N2 C2 1.47(2) . ? N2 H2A 0.8900 . ? N2 H2B 0.8900 . ? N2 H2C 0.8900 . ? C2 H2D 0.9700 . ? C2 H2E 0.9700 . ? N3 C3 1.42(2) . ? N3 C3A 1.53(2) . ? C3 C3A 1.07(2) . ? C3 C3 1.17(4) 4_575 ? C3 C3A 1.51(2) 4_575 ? C3A C3A 0.97(4) 4_575 ? C3A C3 1.51(2) 4_575 ? F6 V2 2.039(2) 4_585 ? 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 101.6(4) . . ? O1 V1 F4 104.4(3) . . ? F3 V1 F4 88.6(2) . . ? O1 V1 F1 97.0(3) . . ? F3 V1 F1 161.1(3) . . ? F4 V1 F1 89.7(2) . . ? O1 V1 F5 101.8(4) . . ? F3 V1 F5 86.6(3) . . ? F4 V1 F5 153.9(3) . . ? F1 V1 F5 86.7(3) . . ? O1 V1 F2 173.6(3) . . ? F3 V1 F2 84.5(3) . . ? F4 V1 F2 73.7(2) . . ? F1 V1 F2 77.0(2) . . ? F5 V1 F2 80.3(3) . . ? O2 V2 F8 101.5(3) . . ? O2 V2 F1 97.6(3) . 3_676 ? F8 V2 F1 160.6(3) . 3_676 ? O2 V2 F2 101.8(3) . . ? F8 V2 F2 88.8(2) . . ? F1 V2 F2 90.8(2) 3_676 . ? O2 V2 F6 100.4(4) . . ? F8 V2 F6 85.4(3) . . ? F1 V2 F6 87.7(3) 3_676 . ? F2 V2 F6 157.7(3) . . ? O2 V2 F4 175.1(3) . . ? F8 V2 F4 81.8(3) . . ? F1 V2 F4 79.4(2) 3_676 . ? F2 V2 F4 74.4(2) . . ? F6 V2 F4 83.5(3) . . ? V1 F5 V1 152.0(5) 4_575 . ? 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 . . ? V2 F2 V1 104.2(2) . . ? V2 F1 V1 155.6(3) 3_676 . ? V1 F4 V2 107.7(3) . . ? N1 C1 C2 111.2(15) . . ? N1 C1 H1D 109.4 . . ? C2 C1 H1D 109.4 . . ? N1 C1 H1E 109.4 . . ? C2 C1 H1E 109.4 . . ? H1D C1 H1E 108.0 . . ? 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 . . ? C1 C2 N2 113.9(15) . . ? C1 C2 H2D 108.8 . . ? N2 C2 H2D 108.8 . . ? C1 C2 H2E 108.8 . . ? N2 C2 H2E 108.8 . . ? H2D C2 H2E 107.7 . . ? C3 N3 C3A 42.5(9) . . ? C3A C3 C3 84.4(15) . 4_575 ? C3A C3 N3 74.6(15) . . ? C3 C3 N3 159.1(8) 4_575 . ? C3A C3 C3A 39.5(17) . 4_575 ? C3 C3 C3A 45.0(9) 4_575 4_575 ? N3 C3 C3A 114.1(13) . 4_575 ? C3A C3A C3 95.6(15) 4_575 . ? C3A C3A C3 45.0(9) 4_575 4_575 ? C3 C3A C3 50.6(18) . 4_575 ? C3A C3A N3 158.5(8) 4_575 . ? C3 C3A N3 62.9(15) . . ? C3 C3A N3 113.5(13) 4_575 . ? V2 F6 V2 154.8(5) 4_585 . ? _diffrn_measured_fraction_theta_max 0.780 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 2.314 _refine_diff_density_min -1.787 _refine_diff_density_rms 0.252 _database_code_depnum_ccdc_archive 'CCDC 957938' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_VOF-14 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H14 N2, F7 O2 V2' _chemical_formula_sum 'C6 H14 F7 N2 O2 V2' _chemical_formula_weight 381.07 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' 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' 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 10.0330(19) _cell_length_b 10.0380(17) _cell_length_c 11.930(2) _cell_angle_alpha 90.00 _cell_angle_beta 110.170(3) _cell_angle_gamma 90.00 _cell_volume 1127.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1335 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.2 _exptl_crystal_description Prism _exptl_crystal_colour Green _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 1.730 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.798 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator confocal _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 5085 _diffrn_reflns_av_R_equivalents 0.1031 _diffrn_reflns_av_sigmaI/netI 0.0578 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 25.52 _reflns_number_total 1046 _reflns_number_gt 891 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_structure_solution 'SHELXS-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^)+(0.1613P)^2^+10.7978P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens NONE _refine_ls_hydrogen_treatment NONE _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1046 _refine_ls_number_parameters 96 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0970 _refine_ls_R_factor_gt 0.0871 _refine_ls_wR_factor_ref 0.2486 _refine_ls_wR_factor_gt 0.2332 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 N1 N 0.3750(7) 0.5850(6) 0.6829(6) 0.0443(16) Uani 1 1 d . . . C3 C 0.3817(13) 0.4871(15) 0.7696(13) 0.096(4) Uani 1 1 d . . . C2A C 0.474(2) 0.535(2) 0.6198(14) 0.063(5) Uani 0.50 1 d P . . C1 C 0.4091(15) 0.7167(17) 0.748(2) 0.166(10) Uani 1 1 d . . . C2B C 0.456(2) 0.640(4) 0.617(3) 0.131(17) Uani 0.50 1 d P . . V1 V -0.05833(12) 0.57932(11) 0.59918(9) 0.0353(6) Uani 1 1 d . . . F1 F 0.0805(5) 0.4170(4) 0.5664(3) 0.0386(10) Uani 1 1 d . . . F2 F 0.1031(5) 0.6771(4) 0.6232(4) 0.0456(11) Uani 1 1 d . . . F4 F 0.0000 0.5220(7) 0.7500 0.0509(15) Uani 1 2 d S . . F5 F -0.1970(5) 0.4518(6) 0.5518(4) 0.0606(14) Uani 1 1 d . . . O1 O -0.1559(7) 0.6992(7) 0.6042(5) 0.0619(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.045(4) 0.046(4) 0.038(4) 0.004(2) 0.008(3) -0.011(2) C3 0.066(7) 0.117(10) 0.096(10) 0.034(8) 0.016(7) -0.015(7) C2A 0.080(13) 0.097(15) 0.013(6) 0.003(8) 0.018(8) -0.019(12) C1 0.054(7) 0.134(13) 0.24(2) -0.095(14) -0.046(11) 0.023(7) C2B 0.042(11) 0.20(3) 0.12(2) 0.13(3) -0.013(12) -0.029(15) V1 0.0324(8) 0.0453(9) 0.0254(8) 0.0002(4) 0.0065(6) -0.0016(4) F1 0.043(2) 0.046(2) 0.024(2) 0.0022(14) 0.0076(18) -0.0010(15) F2 0.051(3) 0.045(2) 0.038(2) -0.0041(17) 0.012(2) -0.0134(18) F4 0.051(4) 0.055(4) 0.048(4) 0.000 0.019(3) 0.000 F5 0.048(3) 0.100(4) 0.032(2) -0.009(2) 0.011(2) -0.031(3) O1 0.065(4) 0.085(4) 0.034(3) 0.003(3) 0.015(3) 0.036(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C3 1.411(14) . ? N1 C2B 1.43(2) . ? N1 C1 1.512(16) . ? N1 C2A 1.52(2) . ? C3 C2A 1.66(3) 2_656 ? C2A C2B 1.06(4) . ? C2A C3 1.66(3) 2_656 ? C1 C1 1.81(4) 2_656 ? C1 C2B 1.88(4) 2_656 ? C1 C2B 1.95(5) . ? C2B C1 1.88(4) 2_656 ? V1 O1 1.565(6) . ? V1 F4 1.785(2) . ? V1 F2 1.830(4) . ? V1 F5 1.831(5) . ? V1 F1 1.911(4) 5_566 ? V1 F1 2.263(4) . ? F1 V1 1.911(4) 5_566 ? F4 V1 1.785(2) 2_556 ? 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 C3 N1 C2B 141.4(14) . . ? C3 N1 C1 106.6(14) . . ? C2B N1 C1 83(2) . . ? C3 N1 C2A 104.9(12) . . ? C2B N1 C2A 42.1(19) . . ? C1 N1 C2A 118.2(13) . . ? N1 C3 C2A 100.9(11) . 2_656 ? C2B C2A N1 64.2(19) . . ? C2B C2A C3 114(2) . 2_656 ? N1 C2A C3 104.0(10) . 2_656 ? N1 C1 C1 93.4(13) . 2_656 ? N1 C1 C2B 92.9(13) . 2_656 ? C1 C1 C2B 63.8(13) 2_656 2_656 ? N1 C1 C2B 46.6(10) . . ? C1 C1 C2B 59.8(16) 2_656 . ? C2B C1 C2B 103.0(11) 2_656 . ? C2A C2B N1 73.7(14) . . ? C2A C2B C1 108.4(17) . 2_656 ? N1 C2B C1 94(2) . 2_656 ? C2A C2B C1 116.5(18) . . ? N1 C2B C1 50.4(15) . . ? C1 C2B C1 56.4(17) 2_656 . ? O1 V1 F4 101.6(3) . . ? O1 V1 F2 96.5(3) . . ? F4 V1 F2 92.90(18) . . ? O1 V1 F5 97.5(4) . . ? F4 V1 F5 92.0(2) . . ? F2 V1 F5 163.9(2) . . ? O1 V1 F1 100.0(2) . 5_566 ? F4 V1 F1 158.3(2) . 5_566 ? F2 V1 F1 86.13(18) . 5_566 ? F5 V1 F1 83.64(19) . 5_566 ? O1 V1 F1 172.0(2) . . ? F4 V1 F1 86.25(19) . . ? F2 V1 F1 81.31(17) . . ? F5 V1 F1 83.7(2) . . ? F1 V1 F1 72.20(18) 5_566 . ? V1 F1 V1 107.80(18) 5_566 . ? V1 F4 V1 142.4(4) 2_556 . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.775 _refine_diff_density_min -0.847 _refine_diff_density_rms 0.181 _database_code_depnum_ccdc_archive 'CCDC 957939'