#------------------------------------------------------------------------------ #$Date: 2015-09-15 06:02:05 +0300 (Tue, 15 Sep 2015) $ #$Revision: 156309 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/53/10/1531040.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1531040 loop_ _publ_author_name 'Gazi, Sarifuddin' 'Ng, Wilson Kwok Hung' 'Rakesh, Ganguly' 'Moeljadi, Adhitya Mangala Putra' 'Hirao, Hajime' 'Soo, Han Sen' _publ_section_title ; Selective Photocatalytic C-C Bond Cleavage under Ambient Conditions with Earth Abundant Vanadium Complexes ; _journal_name_full 'Chem. Sci.' _journal_paper_doi 10.1039/C5SC02923F _journal_year 2015 _chemical_formula_sum 'C16 H16 F N2 O5 V' _chemical_formula_weight 386.25 _chemical_melting_point 438.0(10) _chemical_properties_physical 'Light-sensitive, Photo-sensitive' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _audit_update_record ; 2015-04-10 deposited with the CCDC. 2015-09-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.2079(18) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.9908(3) _cell_length_b 17.1771(6) _cell_length_c 11.9692(5) _cell_measurement_reflns_used 5914 _cell_measurement_temperature 103.(2) _cell_measurement_theta_max 31.0669 _cell_measurement_theta_min 2.8486 _cell_volume 1616.87(11) _computing_cell_refinement 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_data_collection 'APEX2 (Bruker AXS Inc., 2013)' _computing_data_reduction 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_molecular_graphics 'XP (Bruker AXS Inc., 2013)' _computing_publication_material 'APEX2 (Bruker AXS Inc., 2013)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _diffrn_ambient_temperature 103.(2) _diffrn_detector_area_resol_mean 8.3333 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_unetI/netI 0.0322 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 21857 _diffrn_reflns_theta_full 31.09 _diffrn_reflns_theta_max 31.09 _diffrn_reflns_theta_min 2.59 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.655 _exptl_absorpt_correction_T_max 0.93 _exptl_absorpt_correction_T_min 0.82 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2012/1 (Bruker AXS Inc.)' _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.587 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 792 _exptl_crystal_preparation Luminescent _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: methanol' _exptl_crystal_size_max 0.360 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.120 _refine_diff_density_max 0.476 _refine_diff_density_min -0.374 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 232 _refine_ls_number_reflns 5189 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.039 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0332 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0387P)^2^+0.7994P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0816 _refine_ls_wR_factor_ref 0.0872 _reflns_number_gt 4378 _reflns_number_total 5189 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c5sc02923f2.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '437-439' was changed to '438.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius ; _cod_database_code 1531040 _shelx_res_file ; TITL shs27 in P2(1)/c CELL 0.71073 7.99080 17.17710 11.96920 90.0000 100.2079 90.0000 ZERR 4.00 0.00030 0.00060 0.00050 0.0000 0.0018 0.0000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O F V UNIT 64 64 8 20 4 4 L.S. 4 omit 0 1 1 ACTA BOND $H FMAP 2 PLAN 20 SIZE 0.12 0.18 0.36 TEMP -170 WGHT 0.038700 0.799400 FVAR 0.17957 V1 6 0.293010 0.481362 0.248095 11.00000 0.01440 0.01274 = 0.00850 -0.00128 0.00048 -0.00099 C1 1 0.115544 0.381116 0.080009 11.00000 0.01148 0.01183 = 0.01055 -0.00056 0.00101 0.00073 C2 1 0.020164 0.309614 0.041055 11.00000 0.01127 0.01040 = 0.01305 -0.00040 0.00185 -0.00034 C3 1 -0.010136 0.255803 0.122680 11.00000 0.01999 0.01736 = 0.01182 0.00116 0.00138 -0.00451 AFIX 43 H3 2 0.033063 0.265589 0.200570 11.00000 -1.20000 AFIX 0 C4 1 -0.102132 0.188387 0.091988 11.00000 0.02455 0.01705 = 0.01693 0.00242 0.00375 -0.00751 AFIX 43 H4 2 -0.122780 0.151831 0.147538 11.00000 -1.20000 AFIX 0 C5 1 -0.162676 0.176132 -0.021797 11.00000 0.01532 0.01298 = 0.02047 -0.00268 0.00317 -0.00504 C6 1 -0.133578 0.227204 -0.105081 11.00000 0.01995 0.01535 = 0.01335 -0.00323 0.00070 -0.00259 AFIX 43 H6 2 -0.176252 0.216602 -0.182807 11.00000 -1.20000 AFIX 0 C7 1 -0.040966 0.294292 -0.073408 11.00000 0.01979 0.01246 = 0.01295 -0.00016 0.00188 -0.00270 AFIX 43 H7 2 -0.019026 0.329947 -0.129750 11.00000 -1.20000 AFIX 0 C8 1 0.307971 0.544802 0.009186 11.00000 0.01343 0.01223 = 0.01176 -0.00166 0.00286 -0.00041 AFIX 43 H8 2 0.285671 0.540388 -0.071201 11.00000 -1.20000 AFIX 0 C9 1 0.409229 0.609497 0.059307 11.00000 0.01172 0.01163 = 0.01430 -0.00168 0.00218 -0.00106 C10 1 0.427140 0.627189 0.175977 11.00000 0.01360 0.01224 = 0.01481 -0.00114 0.00135 -0.00075 C11 1 0.523452 0.691977 0.219514 11.00000 0.02091 0.01606 = 0.01530 -0.00280 -0.00099 -0.00306 AFIX 43 H11 2 0.536874 0.703828 0.298125 11.00000 -1.20000 AFIX 0 C12 1 0.599217 0.738854 0.148694 11.00000 0.01804 0.01327 = 0.02344 -0.00106 -0.00131 -0.00469 AFIX 43 H12 2 0.664801 0.782541 0.179081 11.00000 -1.20000 AFIX 0 C13 1 0.579949 0.722404 0.033098 11.00000 0.01712 0.01395 = 0.02312 0.00119 0.00400 -0.00271 AFIX 43 H13 2 0.631448 0.755030 -0.015236 11.00000 -1.20000 AFIX 0 C14 1 0.485918 0.658632 -0.010924 11.00000 0.01603 0.01361 = 0.01688 -0.00056 0.00502 -0.00138 AFIX 43 H14 2 0.472769 0.647745 -0.089816 11.00000 -1.20000 AFIX 0 C15 1 0.329895 0.430534 0.484418 11.00000 0.02486 0.01963 = 0.01330 0.00369 0.00328 0.00485 AFIX 137 H15A 2 0.256184 0.388738 0.503273 11.00000 -1.50000 H15B 2 0.353453 0.467242 0.547943 11.00000 -1.50000 H15C 2 0.437005 0.408251 0.470101 11.00000 -1.50000 AFIX 0 C16 1 -0.108744 0.509615 0.280308 11.00000 0.01871 0.04250 = 0.01560 0.00469 0.00661 -0.00114 AFIX 137 H16A 2 -0.133156 0.454089 0.267581 11.00000 -1.50000 H16B 2 -0.212885 0.539793 0.255898 11.00000 -1.50000 H16C 2 -0.066835 0.518756 0.361250 11.00000 -1.50000 AFIX 0 F1 5 -0.254336 0.111289 -0.053250 11.00000 0.03029 0.01850 = 0.02520 -0.00485 0.00554 -0.01355 N1 3 0.245854 0.492422 0.067936 11.00000 0.01200 0.01035 = 0.01052 -0.00166 0.00096 -0.00068 N2 3 0.147826 0.433859 0.007296 11.00000 0.01248 0.01019 = 0.01109 -0.00157 0.00034 -0.00217 O1 4 0.477430 0.444679 0.256595 11.00000 0.01671 0.02321 = 0.01447 -0.00302 -0.00152 0.00207 O2 4 0.164601 0.388539 0.189222 11.00000 0.01977 0.01305 = 0.00956 0.00002 0.00012 -0.00289 O3 4 0.346718 0.586323 0.245022 11.00000 0.02266 0.01565 = 0.01212 -0.00333 0.00416 -0.00559 O4 4 0.017242 0.533180 0.216613 11.00000 0.01489 0.01852 = 0.01071 0.00222 0.00266 -0.00015 H1O 2 -0.024870 0.542041 0.149905 11.00000 0.03244 O5 4 0.247577 0.470091 0.386049 11.00000 0.01943 0.01634 = 0.00905 0.00002 0.00059 0.00121 HKLF 4 REM shs27 in P2(1)/c REM R1 = 0.0332 for 4378 Fo > 4sig(Fo) and 0.0426 for all 5189 data REM 232 parameters refined using 0 restraints END WGHT 0.0374 0.8130 REM Highest difference peak 0.476, deepest hole -0.374, 1-sigma level 0.068 Q1 1 0.5017 0.6527 0.1999 11.00000 0.05 0.48 Q2 1 0.5497 0.7164 0.1801 11.00000 0.05 0.45 Q3 1 0.4489 0.6340 0.0263 11.00000 0.05 0.45 Q4 1 -0.0907 0.2640 -0.0897 11.00000 0.05 0.44 Q5 1 -0.1225 0.1828 0.0344 11.00000 0.05 0.44 Q6 1 0.0086 0.2845 0.0779 11.00000 0.05 0.43 Q7 1 -0.0189 0.2983 -0.0151 11.00000 0.05 0.43 Q8 1 0.0679 0.3426 0.0635 11.00000 0.05 0.42 Q9 1 0.5800 0.7294 0.0867 11.00000 0.05 0.39 Q10 1 -0.1273 0.2001 -0.0617 11.00000 0.05 0.39 Q11 1 0.1420 0.3815 0.1393 11.00000 0.05 0.39 Q12 1 0.3733 0.5737 0.0388 11.00000 0.05 0.38 Q13 1 0.4052 0.4696 0.2542 11.00000 0.05 0.38 Q14 1 0.4061 0.6162 0.1154 11.00000 0.05 0.38 Q15 1 0.2967 0.4765 0.3369 11.00000 0.05 0.37 Q16 1 0.5360 0.6909 0.0128 11.00000 0.05 0.35 Q17 1 0.2523 0.5263 0.0409 11.00000 0.05 0.35 Q18 1 -0.0463 0.2217 0.0956 11.00000 0.05 0.34 Q19 1 0.3788 0.4515 0.2419 11.00000 0.05 0.34 Q20 1 0.1223 0.4163 0.0549 11.00000 0.05 0.32 ; _shelx_res_checksum 35761 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags_adp _atom_site_refinement_flags_posn _atom_site_occupancy V V1 0.29301(3) 0.48136(2) 0.24810(2) 0.01207(6) Uani d . . 1 C C1 0.11554(16) 0.38112(7) 0.08001(10) 0.0114(2) Uani d . . 1 C C2 0.02016(16) 0.30961(7) 0.04105(11) 0.0116(2) Uani d . . 1 C C3 -0.01014(18) 0.25580(8) 0.12268(11) 0.0166(3) Uani d . . 1 H H3 0.0331 0.2656 0.2006 0.02 Uiso calc U R 1 C C4 -0.1021(2) 0.18839(8) 0.09199(12) 0.0195(3) Uani d . . 1 H H4 -0.1228 0.1518 0.1475 0.023 Uiso calc U R 1 C C5 -0.16268(18) 0.17613(8) -0.02180(12) 0.0163(3) Uani d . . 1 C C6 -0.13358(18) 0.22720(8) -0.10508(11) 0.0165(3) Uani d . . 1 H H6 -0.1763 0.2166 -0.1828 0.02 Uiso calc U R 1 C C7 -0.04097(18) 0.29429(8) -0.07341(11) 0.0152(2) Uani d . . 1 H H7 -0.019 0.3299 -0.1297 0.018 Uiso calc U R 1 C C8 0.30797(17) 0.54480(7) 0.00919(11) 0.0124(2) Uani d . . 1 H H8 0.2857 0.5404 -0.0712 0.015 Uiso calc U R 1 C C9 0.40923(17) 0.60950(7) 0.05931(11) 0.0126(2) Uani d . . 1 C C10 0.42714(17) 0.62719(7) 0.17598(11) 0.0137(2) Uani d . . 1 C C11 0.52345(19) 0.69198(8) 0.21951(12) 0.0179(3) Uani d . . 1 H H11 0.5369 0.7038 0.2981 0.022 Uiso calc U R 1 C C12 0.59922(19) 0.73885(8) 0.14869(12) 0.0189(3) Uani d . . 1 H H12 0.6648 0.7825 0.1791 0.023 Uiso calc U R 1 C C13 0.57995(18) 0.72240(8) 0.03310(12) 0.0180(3) Uani d . . 1 H H13 0.6314 0.755 -0.0152 0.022 Uiso calc U R 1 C C14 0.48592(18) 0.65863(8) -0.01092(12) 0.0152(2) Uani d . . 1 H H14 0.4728 0.6477 -0.0898 0.018 Uiso calc U R 1 C C15 0.3299(2) 0.43053(8) 0.48442(12) 0.0193(3) Uani d . . 1 H H15A 0.2562 0.3887 0.5033 0.029 Uiso calc U R 1 H H15B 0.3535 0.4672 0.5479 0.029 Uiso calc U R 1 H H15C 0.437 0.4083 0.4701 0.029 Uiso calc U R 1 C C16 -0.1087(2) 0.50962(11) 0.28031(13) 0.0252(3) Uani d . . 1 H H16A -0.1332 0.4541 0.2676 0.038 Uiso calc U R 1 H H16B -0.2129 0.5398 0.2559 0.038 Uiso calc U R 1 H H16C -0.0668 0.5188 0.3613 0.038 Uiso calc U R 1 F F1 -0.25434(12) 0.11129(5) -0.05325(8) 0.0246(2) Uani d . . 1 N N1 0.24585(14) 0.49242(6) 0.06794(9) 0.0111(2) Uani d . . 1 N N2 0.14783(14) 0.43386(6) 0.00730(9) 0.0115(2) Uani d . . 1 O O1 0.47743(13) 0.44468(6) 0.25660(8) 0.0187(2) Uani d . . 1 O O2 0.16460(13) 0.38854(5) 0.18922(8) 0.01443(19) Uani d . . 1 O O3 0.34672(13) 0.58632(6) 0.24502(8) 0.0167(2) Uani d . . 1 O O4 0.01724(13) 0.53318(6) 0.21661(8) 0.01466(19) Uani d . . 1 H H1O -0.025(3) 0.5420(12) 0.1499(19) 0.032(6) Uiso d . . 1 O O5 0.24758(13) 0.47009(6) 0.38605(8) 0.01517(19) Uani d . . 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 V1 0.01440(12) 0.01274(10) 0.00850(10) -0.00099(8) 0.00048(7) -0.00128(7) C1 0.0115(6) 0.0118(5) 0.0105(5) 0.0007(4) 0.0010(4) -0.0006(4) C2 0.0113(6) 0.0104(5) 0.0131(5) -0.0003(4) 0.0018(4) -0.0004(4) C3 0.0200(7) 0.0174(6) 0.0118(6) -0.0045(5) 0.0014(5) 0.0012(4) C4 0.0245(7) 0.0171(6) 0.0169(6) -0.0075(5) 0.0038(5) 0.0024(5) C5 0.0153(6) 0.0130(6) 0.0205(6) -0.0050(5) 0.0032(5) -0.0027(5) C6 0.0200(7) 0.0154(6) 0.0133(6) -0.0026(5) 0.0007(5) -0.0032(4) C7 0.0198(7) 0.0125(5) 0.0130(6) -0.0027(5) 0.0019(5) -0.0002(4) C8 0.0134(6) 0.0122(5) 0.0118(5) -0.0004(5) 0.0029(4) -0.0017(4) C9 0.0117(6) 0.0116(5) 0.0143(6) -0.0011(4) 0.0022(4) -0.0017(4) C10 0.0136(6) 0.0122(5) 0.0148(6) -0.0008(5) 0.0014(5) -0.0011(4) C11 0.0209(7) 0.0161(6) 0.0153(6) -0.0031(5) -0.0010(5) -0.0028(5) C12 0.0180(7) 0.0133(6) 0.0234(7) -0.0047(5) -0.0013(5) -0.0011(5) C13 0.0171(7) 0.0139(6) 0.0231(7) -0.0027(5) 0.0040(5) 0.0012(5) C14 0.0160(6) 0.0136(6) 0.0169(6) -0.0014(5) 0.0050(5) -0.0006(5) C15 0.0249(7) 0.0196(6) 0.0133(6) 0.0048(6) 0.0033(5) 0.0037(5) C16 0.0187(7) 0.0425(9) 0.0156(7) -0.0011(7) 0.0066(5) 0.0047(6) F1 0.0303(5) 0.0185(4) 0.0252(5) -0.0135(4) 0.0055(4) -0.0048(3) N1 0.0120(5) 0.0103(4) 0.0105(5) -0.0007(4) 0.0010(4) -0.0017(4) N2 0.0125(5) 0.0102(4) 0.0111(5) -0.0022(4) 0.0003(4) -0.0016(4) O1 0.0167(5) 0.0232(5) 0.0145(4) 0.0021(4) -0.0015(4) -0.0030(4) O2 0.0198(5) 0.0130(4) 0.0096(4) -0.0029(4) 0.0001(3) 0.0000(3) O3 0.0227(5) 0.0157(4) 0.0121(4) -0.0056(4) 0.0042(4) -0.0033(3) O4 0.0149(5) 0.0185(4) 0.0107(4) -0.0002(4) 0.0027(3) 0.0022(3) O5 0.0194(5) 0.0163(4) 0.0090(4) 0.0012(4) 0.0006(3) 0.0000(3) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O1 V1 O5 103.83(5) O1 V1 O3 99.87(5) O5 V1 O3 102.24(4) O1 V1 O2 96.95(5) O5 V1 O2 93.78(4) O3 V1 O2 153.17(4) O1 V1 N1 95.50(5) O5 V1 N1 158.25(5) O3 V1 N1 83.88(4) O2 V1 N1 73.80(4) O1 V1 O4 174.45(4) O5 V1 O4 81.29(4) O3 V1 O4 80.91(4) O2 V1 O4 80.42(4) N1 V1 O4 79.10(4) O2 C1 N2 122.55(11) O2 C1 C2 116.42(11) N2 C1 C2 121.04(11) C7 C2 C3 119.20(12) C7 C2 C1 122.55(11) C3 C2 C1 118.24(11) C4 C3 C2 121.13(12) C4 C3 H3 119.4 C2 C3 H3 119.4 C5 C4 C3 117.80(12) C5 C4 H4 121.1 C3 C4 H4 121.1 F1 C5 C6 118.45(12) F1 C5 C4 118.68(12) C6 C5 C4 122.87(12) C5 C6 C7 118.81(12) C5 C6 H6 120.6 C7 C6 H6 120.6 C6 C7 C2 120.16(12) C6 C7 H7 119.9 C2 C7 H7 119.9 N1 C8 C9 123.44(12) N1 C8 H8 118.3 C9 C8 H8 118.3 C14 C9 C10 118.93(12) C14 C9 C8 119.07(11) C10 C9 C8 121.93(12) O3 C10 C11 118.78(12) O3 C10 C9 121.64(11) C11 C10 C9 119.48(12) C12 C11 C10 120.38(13) C12 C11 H11 119.8 C10 C11 H11 119.8 C11 C12 C13 120.45(13) C11 C12 H12 119.8 C13 C12 H12 119.8 C14 C13 C12 119.82(13) C14 C13 H13 120.1 C12 C13 H13 120.1 C13 C14 C9 120.93(13) C13 C14 H14 119.5 C9 C14 H14 119.5 O5 C15 H15A 109.5 O5 C15 H15B 109.5 H15A C15 H15B 109.5 O5 C15 H15C 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 O4 C16 H16A 109.5 O4 C16 H16B 109.5 H16A C16 H16B 109.5 O4 C16 H16C 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 C8 N1 N2 116.89(11) C8 N1 V1 126.58(9) N2 N1 V1 116.36(8) C1 N2 N1 108.09(10) C1 O2 V1 119.08(8) C10 O3 V1 131.51(8) C16 O4 V1 122.63(9) C16 O4 H1O 111.4(15) V1 O4 H1O 115.9(15) C15 O5 V1 133.54(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance V1 O1 1.5893(11) V1 O5 1.7630(10) V1 O3 1.8552(10) V1 O2 1.9584(9) V1 N1 2.1307(11) V1 O4 2.3443(10) C1 O2 1.3027(15) C1 N2 1.3131(16) C1 C2 1.4768(17) C2 C7 1.3956(18) C2 C3 1.3969(18) C3 C4 1.3859(19) C3 H3 0.95 C4 C5 1.3783(19) C4 H4 0.95 C5 F1 1.3495(15) C5 C6 1.3782(19) C6 C7 1.3856(18) C6 H6 0.95 C7 H7 0.95 C8 N1 1.2939(16) C8 C9 1.4413(17) C8 H8 0.95 C9 C14 1.4061(18) C9 C10 1.4114(18) C10 O3 1.3330(16) C10 C11 1.4001(18) C11 C12 1.384(2) C11 H11 0.95 C12 C13 1.394(2) C12 H12 0.95 C13 C14 1.3791(19) C13 H13 0.95 C14 H14 0.95 C15 O5 1.4164(16) C15 H15A 0.98 C15 H15B 0.98 C15 H15C 0.98 C16 O4 1.4250(17) C16 H16A 0.98 C16 H16B 0.98 C16 H16C 0.98 N1 N2 1.3967(14) O4 H1O 0.82(2)