#------------------------------------------------------------------------------ #$Date: 2026-06-02 23:54:29 +0100 (Tue, 02 Jun 2026) $ #$Revision: 306170 $ #$URL: svn://www.crystallography.net/cod/cif/7/72/10/7721069.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_7721069 loop_ _publ_author_name 'Matusiewicz, Barbara' 'Tesmar, Aleksandra' 'Brzeski, Jakub' 'Freza, Sylwia' 'Kazimierczuk, Katarzyna' 'Wyrzykowski, Dariusz' _publ_section_title ; Stereochemical control and its consequences in VO(acac)2 complexes: an integrated study of trans/cis isomerism with quinoline and isoquinoline ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/D6DT01029F _journal_year 2026 _chemical_absolute_configuration unk _chemical_formula_moiety 'C19 H21 N O5 V' _chemical_formula_sum 'C19 H21 N O5 V' _chemical_formula_weight 394.31 _chemical_name_systematic ; trans-bis(acetylacetonato-k2O,O')oxido(isoquinoline-kN)vanadium(IV) ; _space_group_IT_number 8 _space_group_name_Hall 'C -2y' _space_group_name_H-M_alt 'C 1 m 1' _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 8 _symmetry_space_group_name_Hall 'C -2y' _symmetry_space_group_name_H-M 'C 1 m 1' _atom_sites_solution_hydrogens geom _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_creation_date 2025-06-10 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_update_record ; 2026-04-13 deposited with the CCDC. 2026-06-01 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.419(5) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 8.7229(6) _cell_length_b 13.5442(8) _cell_length_c 8.0885(5) _cell_measurement_reflns_used 19664 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 29.53 _cell_measurement_theta_min 2.52 _cell_volume 955.59(10) _computing_molecular_graphics 'Ortep for Windows (Farrugia, 2012)' _computing_publication_material 'WinGX publication routines (Farrugia, 2012)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 120(2) _diffrn_detector 'image plate (34 cm diameter)' _diffrn_detector_area_resol_mean 6.67 _diffrn_detector_type STOE _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2T' _diffrn_measurement_method 'rotation method' _diffrn_radiation_monochromator 'parabolic x-ray mirror' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_unetI/netI 0.0224 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 7425 _diffrn_reflns_point_group_measured_fraction_full 0.959 _diffrn_reflns_point_group_measured_fraction_max 0.945 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.151 _diffrn_reflns_theta_min 2.518 _diffrn_source 'GeniX Mo, 0.05 x 0.05 mm2 microfocus' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.547 _exptl_absorpt_correction_T_max 0.9650 _exptl_absorpt_correction_T_min 0.9095 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Numerical absorption correction was performed after the optimization of the crystal-shape description due to Herrendorf?s method [Herrendorf, 1994] Herrendorf, W. (1994).HABITUS, a program for the optimization of the crystal description for the numerical absorption correction by means of suitable, psi scanned reflections;dissertation 1994,Karlsruhe;extension 1998,Gie\&sen ; _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.37 _exptl_crystal_description plate _exptl_crystal_F_000 410 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.321 _refine_diff_density_min -0.709 _refine_diff_density_rms 0.07 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack 0.24(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 139 _refine_ls_number_reflns 2530 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.083 _refine_ls_R_factor_all 0.0473 _refine_ls_R_factor_gt 0.0445 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0722P)^2^+1.3041P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1161 _refine_ls_wR_factor_ref 0.1243 _reflns_Friedel_coverage 0.892 _reflns_Friedel_fraction_full 0.919 _reflns_Friedel_fraction_max 0.894 _reflns_number_gt 2430 _reflns_number_total 2530 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6dt01029f2.cif _cod_data_source_block at4_2024 _cod_original_sg_symbol_H-M 'C m' _cod_database_code 7721069 _shelx_shelxl_version_number 2018/3 _shelx_res_file ; TITL at4_2024_a.res in Cm New:Cm shelx.res created by SHELXL-2018/3 at 13:56:20 on 10-Jun-2025 CELL 0.71073 8.7229 13.5442 8.0885 90.000 90.419 90.000 ZERR 2.00 0.0006 0.0008 0.0005 0.000 0.005 0.000 LATT -7 SYMM X, - Y, Z SFAC C H N O V UNIT 38 42 2 10 2 MERG 2 TWIN MORE -1 FMAP 2 PLAN 10 ACTA BOND $H CONF L.S. 60 TEMP -153.15 WGHT 0.072200 1.304100 BASF 0.23871 FVAR 0.86056 C1 1 0.512825 0.252589 0.926229 11.00000 0.04455 0.04077 = 0.04135 0.00702 0.00071 -0.01244 AFIX 137 H1A 2 0.492363 0.186554 0.881731 11.00000 -1.50000 H1B 2 0.415517 0.286694 0.945626 11.00000 -1.50000 H1C 2 0.569706 0.246796 1.030711 11.00000 -1.50000 AFIX 0 C2 1 0.605953 0.310288 0.804819 11.00000 0.02882 0.02896 = 0.03231 0.00315 -0.00536 -0.00237 C3 1 0.644055 0.268324 0.652833 11.00000 0.03503 0.03060 = 0.03888 -0.00062 -0.00285 -0.00167 AFIX 43 H3 2 0.602790 0.205195 0.627210 11.00000 -1.20000 AFIX 0 C4 1 0.738307 0.312684 0.536453 11.00000 0.03081 0.02907 = 0.03330 -0.00440 -0.00381 0.00222 C5 1 0.776966 0.259536 0.379691 11.00000 0.05112 0.03980 = 0.04088 -0.01179 0.00181 -0.00331 AFIX 137 H5A 2 0.875332 0.225431 0.393340 11.00000 -1.50000 H5B 2 0.784267 0.307217 0.288958 11.00000 -1.50000 H5C 2 0.696579 0.211204 0.354263 11.00000 -1.50000 AFIX 0 C6 1 0.384630 0.500000 0.663198 10.50000 0.03075 0.04420 = 0.02135 0.00000 0.00046 0.00000 AFIX 43 H6 2 0.392184 0.500000 0.780425 10.50000 -1.20000 AFIX 0 C7 1 0.242647 0.500000 0.593341 10.50000 0.02431 0.03988 = 0.02717 0.00000 0.00127 0.00000 AFIX 43 H7 2 0.153991 0.500000 0.660862 10.50000 -1.20000 AFIX 0 C8 1 0.227936 0.500000 0.418777 10.50000 0.02900 0.02742 = 0.02425 0.00000 -0.00154 0.00000 C9 1 0.084078 0.500000 0.335375 10.50000 0.02450 0.04908 = 0.02709 0.00000 -0.00083 0.00000 AFIX 43 H9 2 -0.008284 0.500000 0.396886 10.50000 -1.20000 AFIX 0 C10 1 0.078800 0.500000 0.166994 10.50000 0.02620 0.07084 = 0.03050 0.00000 -0.00221 0.00000 AFIX 43 H10 2 -0.017607 0.500000 0.111591 10.50000 -1.20000 AFIX 0 C11 1 0.214379 0.500000 0.074518 10.50000 0.02847 0.09958 = 0.02281 0.00000 -0.00125 0.00000 AFIX 43 H11 2 0.207821 0.500000 -0.042771 10.50000 -1.20000 AFIX 0 C12 1 0.356534 0.500000 0.149445 10.50000 0.02881 0.07198 = 0.01969 0.00000 0.00446 0.00000 AFIX 43 H12 2 0.447308 0.500000 0.085260 10.50000 -1.20000 AFIX 0 C13 1 0.364454 0.500000 0.324304 10.50000 0.02162 0.03644 = 0.02147 0.00000 0.00011 0.00000 C14 1 0.506416 0.500000 0.411129 10.50000 0.02338 0.03626 = 0.02381 0.00000 0.00004 0.00000 AFIX 43 H14 2 0.598507 0.500000 0.349150 10.50000 -1.20000 AFIX 0 N1 3 0.516443 0.500000 0.574962 10.50000 0.02517 0.03570 = 0.02476 0.00000 -0.00097 0.00000 O1 4 0.919819 0.500000 0.816036 10.50000 0.02802 0.03493 = 0.03226 0.00000 -0.00408 0.00000 O2 4 0.645123 0.397193 0.853180 11.00000 0.02874 0.03152 = 0.02698 0.00225 -0.00122 -0.00254 O3 4 0.798406 0.398376 0.550719 11.00000 0.02843 0.03016 = 0.02982 -0.00430 -0.00033 -0.00057 V1 5 0.756331 0.500000 0.723392 10.50000 0.02212 0.02923 = 0.02502 0.00000 -0.00300 0.00000 HKLF 4 1.0 -1.00 0.00 0.00 0.00 -1.00 0.00 0.00 0.00 1.00 REM at4_2024_a.res in Cm New:Cm REM wR2 = 0.1243, GooF = S = 1.083, Restrained GooF = 1.083 for all data REM R1 = 0.0445 for 2430 Fo > 4sig(Fo) and 0.0473 for all 2530 data REM 139 parameters refined using 2 restraints END WGHT 0.0722 1.3041 REM Highest difference peak 0.321, deepest hole -0.709, 1-sigma level 0.070 Q1 1 0.6227 0.5000 0.6704 10.50000 0.05 0.32 Q2 1 0.6602 0.4204 0.7192 11.00000 0.05 0.31 Q3 1 0.9901 0.5000 0.9336 10.50000 0.05 0.30 Q4 1 0.5222 0.5000 -0.0363 10.50000 0.05 0.30 Q5 1 0.9823 0.5000 0.6545 10.50000 0.05 0.30 Q6 1 0.5079 0.5000 0.7362 10.50000 0.05 0.29 Q7 1 0.6809 0.5623 0.6395 11.00000 0.05 0.29 Q8 1 0.5190 0.5000 0.4938 10.50000 0.05 0.28 Q9 1 0.6356 0.5000 0.9278 10.50000 0.05 0.26 Q10 1 0.6884 0.5000 0.8504 10.50000 0.05 0.26 ; loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5128(6) 0.2526(4) 0.9262(6) 0.0422(10) Uani 1 1 d . . . . . H1A H 0.492363 0.186554 0.881731 0.063 Uiso 1 1 calc R U . . . H1B H 0.415517 0.286694 0.945626 0.063 Uiso 1 1 calc R U . . . H1C H 0.569706 0.246796 1.030711 0.063 Uiso 1 1 calc R U . . . C2 C 0.6060(5) 0.3103(3) 0.8048(5) 0.0301(8) Uani 1 1 d . . . . . C3 C 0.6441(5) 0.2683(3) 0.6528(6) 0.0349(8) Uani 1 1 d . . . . . H3 H 0.60279 0.205195 0.62721 0.042 Uiso 1 1 calc R U . . . C4 C 0.7383(5) 0.3127(3) 0.5365(5) 0.0311(8) Uani 1 1 d . . . . . C5 C 0.7770(6) 0.2595(4) 0.3797(6) 0.0439(10) Uani 1 1 d . . . . . H5A H 0.875332 0.225431 0.39334 0.066 Uiso 1 1 calc R U . . . H5B H 0.784267 0.307217 0.288958 0.066 Uiso 1 1 calc R U . . . H5C H 0.696579 0.211204 0.354263 0.066 Uiso 1 1 calc R U . . . C6 C 0.3846(7) 0.5 0.6632(7) 0.0321(11) Uani 1 2 d S T P . . H6 H 0.392184 0.5 0.780425 0.039 Uiso 1 2 calc R U P . . C7 C 0.2426(6) 0.5 0.5933(7) 0.0304(11) Uani 1 2 d S T P . . H7 H 0.153991 0.5 0.660862 0.037 Uiso 1 2 calc R U P . . C8 C 0.2279(7) 0.5 0.4188(7) 0.0269(10) Uani 1 2 d S T P . . C9 C 0.0841(7) 0.5 0.3354(7) 0.0336(12) Uani 1 2 d S T P . . H9 H -0.008284 0.5 0.396886 0.04 Uiso 1 2 calc R U P . . C10 C 0.0788(8) 0.5 0.1670(8) 0.0425(15) Uani 1 2 d S T P . . H10 H -0.017607 0.5 0.111591 0.051 Uiso 1 2 calc R U P . . C11 C 0.2144(9) 0.5 0.0745(8) 0.050(2) Uani 1 2 d S T P . . H11 H 0.207821 0.5 -0.042771 0.06 Uiso 1 2 calc R U P . . C12 C 0.3565(8) 0.5 0.1494(7) 0.0401(15) Uani 1 2 d S T P . . H12 H 0.447308 0.5 0.08526 0.048 Uiso 1 2 calc R U P . . C13 C 0.3645(7) 0.5 0.3243(7) 0.0265(10) Uani 1 2 d S T P . . C14 C 0.5064(6) 0.5 0.4111(7) 0.0278(10) Uani 1 2 d S T P . . H14 H 0.598507 0.5 0.34915 0.033 Uiso 1 2 calc R U P . . N1 N 0.5164(6) 0.5 0.5750(6) 0.0285(9) Uani 1 2 d S T P . . O1 O 0.9198(5) 0.5 0.8160(5) 0.0318(8) Uani 1 2 d S T P . . O2 O 0.6451(3) 0.3972(2) 0.8532(3) 0.0291(6) Uani 1 1 d . . . . . O3 O 0.7984(3) 0.3984(2) 0.5507(4) 0.0295(6) Uani 1 1 d . . . . . V1 V 0.75633(8) 0.5 0.72339(8) 0.0255(2) Uani 1 2 d S T P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.045(3) 0.041(2) 0.041(2) 0.0070(19) 0.0007(19) -0.012(2) C2 0.0288(18) 0.0290(17) 0.0323(18) 0.0031(14) -0.0054(14) -0.0024(14) C3 0.035(2) 0.0306(17) 0.039(2) -0.0006(17) -0.0028(16) -0.0017(16) C4 0.0308(18) 0.0291(16) 0.0333(19) -0.0044(14) -0.0038(14) 0.0022(15) C5 0.051(3) 0.040(2) 0.041(2) -0.0118(19) 0.002(2) -0.003(2) C6 0.031(3) 0.044(3) 0.021(2) 0 0.000(2) 0 C7 0.024(2) 0.040(3) 0.027(2) 0 0.0013(19) 0 C8 0.029(3) 0.027(2) 0.024(2) 0 -0.0015(19) 0 C9 0.025(3) 0.049(3) 0.027(2) 0 -0.001(2) 0 C10 0.026(3) 0.071(4) 0.030(3) 0 -0.002(2) 0 C11 0.028(3) 0.100(6) 0.023(3) 0 -0.001(2) 0 C12 0.029(3) 0.072(4) 0.020(3) 0 0.004(2) 0 C13 0.022(2) 0.036(3) 0.021(2) 0 0.0001(19) 0 C14 0.023(2) 0.036(3) 0.024(2) 0 0.0000(18) 0 N1 0.025(2) 0.036(2) 0.025(2) 0 -0.0010(17) 0 O1 0.028(2) 0.035(2) 0.032(2) 0 -0.0041(16) 0 O2 0.0287(14) 0.0315(13) 0.0270(13) 0.0022(10) -0.0012(10) -0.0025(11) O3 0.0284(14) 0.0302(13) 0.0298(13) -0.0043(10) -0.0003(11) -0.0006(11) V1 0.0221(4) 0.0292(4) 0.0250(4) 0 -0.0030(3) 0 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 0 '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 0.006 '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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -3 1 0 0.0510 3 -1 0 0.1040 1 0 -3 0.1110 0 0 1 0.0900 0 -1 0 0.0300 -1 -1 -1 0.0860 0 1 0 0.0340 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 C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 C3 125.2(4) . . ? O2 C2 C1 115.0(4) . . ? C3 C2 C1 119.9(4) . . ? C4 C3 C2 124.4(4) . . ? C4 C3 H3 117.8 . . ? C2 C3 H3 117.8 . . ? O3 C4 C3 125.1(4) . . ? O3 C4 C5 114.7(4) . . ? C3 C4 C5 120.2(4) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 N1 123.7(5) . . ? C7 C6 H6 118.2 . . ? N1 C6 H6 118.2 . . ? C6 C7 C8 119.4(5) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C7 C8 C13 117.8(5) . . ? C7 C8 C9 123.1(5) . . ? C13 C8 C9 119.1(5) . . ? C10 C9 C8 119.9(6) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 120.7(6) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C12 C11 C10 121.7(6) . . ? C12 C11 H11 119.2 . . ? C10 C11 H11 119.2 . . ? C11 C12 C13 118.5(5) . . ? C11 C12 H12 120.7 . . ? C13 C12 H12 120.7 . . ? C12 C13 C14 122.0(5) . . ? C12 C13 C8 120.2(5) . . ? C14 C13 C8 117.8(5) . . ? N1 C14 C13 123.0(5) . . ? N1 C14 H14 118.5 . . ? C13 C14 H14 118.5 . . ? C14 N1 C6 118.4(5) . . ? C14 N1 V1 123.3(4) . . ? C6 N1 V1 118.3(4) . . ? C2 O2 V1 127.4(3) . . ? C4 O3 V1 127.7(3) . . ? O1 V1 O3 99.16(15) . 2_565 ? O1 V1 O3 99.16(15) . . ? O3 V1 O3 87.15(17) 2_565 . ? O1 V1 O2 100.81(14) . 2_565 ? O3 V1 O2 88.83(11) 2_565 2_565 ? O3 V1 O2 160.01(11) . 2_565 ? O1 V1 O2 100.81(14) . . ? O3 V1 O2 160.01(11) 2_565 . ? O3 V1 O2 88.83(11) . . ? O2 V1 O2 88.29(17) 2_565 . ? O1 V1 N1 177.9(2) . . ? O3 V1 N1 79.31(12) 2_565 . ? O3 V1 N1 79.31(12) . . ? O2 V1 N1 80.70(12) 2_565 . ? O2 V1 N1 80.70(12) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.499(6) . ? C1 H1A 0.98 . ? C1 H1B 0.98 . ? C1 H1C 0.98 . ? C2 O2 1.286(5) . ? C2 C3 1.397(6) . ? C3 C4 1.391(6) . ? C3 H3 0.95 . ? C4 O3 1.278(5) . ? C4 C5 1.499(6) . ? C5 H5A 0.98 . ? C5 H5B 0.98 . ? C5 H5C 0.98 . ? C6 C7 1.358(8) . ? C6 N1 1.358(8) . ? C6 H6 0.95 . ? C7 C8 1.417(7) . ? C7 H7 0.95 . ? C8 C13 1.420(8) . ? C8 C9 1.420(7) . ? C9 C10 1.362(8) . ? C9 H9 0.95 . ? C10 C11 1.404(10) . ? C10 H10 0.95 . ? C11 C12 1.376(9) . ? C11 H11 0.95 . ? C12 C13 1.416(8) . ? C12 H12 0.95 . ? C13 C14 1.419(7) . ? C14 N1 1.327(7) . ? C14 H14 0.95 . ? N1 V1 2.405(5) . ? O1 V1 1.606(4) . ? O2 V1 1.999(3) . ? O3 V1 1.997(3) . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C2 C3 C4 4.3(7) . . . . ? C1 C2 C3 C4 -175.4(4) . . . . ? C2 C3 C4 O3 -2.2(7) . . . . ? C2 C3 C4 C5 177.6(4) . . . . ? N1 C6 C7 C8 0.0000(10) . . . . ? C6 C7 C8 C13 0.0000(10) . . . . ? C6 C7 C8 C9 180.0000(10) . . . . ? C7 C8 C9 C10 180.0000(10) . . . . ? C13 C8 C9 C10 0.0000(10) . . . . ? C8 C9 C10 C11 0.0000(10) . . . . ? C9 C10 C11 C12 0.0000(10) . . . . ? C10 C11 C12 C13 0.0000(10) . . . . ? C11 C12 C13 C14 180 . . . . ? C11 C12 C13 C8 0.0000(10) . . . . ? C7 C8 C13 C12 180.0000(10) . . . . ? C9 C8 C13 C12 0.0000(10) . . . . ? C7 C8 C13 C14 0.0000(10) . . . . ? C9 C8 C13 C14 180.0000(10) . . . . ? C12 C13 C14 N1 180.0000(10) . . . . ? C8 C13 C14 N1 0.0000(10) . . . . ? C13 C14 N1 C6 0.0000(10) . . . . ? C13 C14 N1 V1 180 . . . . ? C7 C6 N1 C14 0.0000(10) . . . . ? C7 C6 N1 V1 180.0000(10) . . . . ? C3 C2 O2 V1 4.7(6) . . . . ? C1 C2 O2 V1 -175.6(3) . . . . ? C3 C4 O3 V1 -8.6(6) . . . . ? C5 C4 O3 V1 171.5(3) . . . . ?