#------------------------------------------------------------------------------ #$Date: 2026-06-02 23:54:29 +0100 (Tue, 02 Jun 2026) $ #$Revision: 306170 $ #$URL: svn://www.crystallography.net/cod/cif/7/72/10/7721070.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_7721070 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 'C10 H14 O5 V, C9 H7 N' _chemical_formula_sum 'C19 H21 N O5 V' _chemical_formula_weight 394.31 _chemical_name_systematic ; trans-bis(acetylacetonato-k2O,O')oxido(quinoline-kN)vanadium(IV) ; _space_group_IT_number 7 _space_group_name_Hall 'P -2yac' _space_group_name_H-M_alt 'P 1 n 1' _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 7 _symmetry_space_group_name_Hall 'P -2yac' _symmetry_space_group_name_H-M 'P 1 n 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 2025-06-11 _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 96.296(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 8.0583(3) _cell_length_b 7.7264(4) _cell_length_c 15.3312(6) _cell_measurement_reflns_used 30748 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 29.66 _cell_measurement_theta_min 2.54 _cell_volume 948.79(7) _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 0.998 _diffrn_measured_fraction_theta_max 0.994 _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 0.0276 _diffrn_reflns_av_unetI/netI 0.0213 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 14705 _diffrn_reflns_point_group_measured_fraction_full 0.965 _diffrn_reflns_point_group_measured_fraction_max 0.95 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.212 _diffrn_reflns_theta_min 2.636 _diffrn_source 'GeniX Mo, 0.05 x 0.05 mm2 microfocus' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.551 _exptl_absorpt_correction_T_max 0.9502 _exptl_absorpt_correction_T_min 0.9001 _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 1.38 _exptl_crystal_description plate _exptl_crystal_F_000 410 _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.681 _refine_diff_density_min -0.596 _refine_diff_density_rms 0.06 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack 0.08(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 240 _refine_ls_number_reflns 4882 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.052 _refine_ls_R_factor_all 0.0387 _refine_ls_R_factor_gt 0.0362 _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^)+(0.0699P)^2^+0.2568P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0967 _refine_ls_wR_factor_ref 0.1012 _reflns_Friedel_coverage 0.908 _reflns_Friedel_fraction_full 0.932 _reflns_Friedel_fraction_max 0.906 _reflns_number_gt 4626 _reflns_number_total 4882 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6dt01029f2.cif _cod_data_source_block at6_2024 _cod_original_sg_symbol_H-M 'P n' _cod_database_code 7721070 _shelx_shelxl_version_number 2018/3 _shelx_res_file ; TITL at6_2024_a.res in Pn shelx.res created by SHELXL-2018/3 at 10:48:55 on 11-Jun-2025 CELL 0.71073 8.0583 7.7264 15.3312 90.000 96.296 90.000 ZERR 2.00 0.0003 0.0004 0.0006 0.000 0.003 0.000 LATT -1 SYMM 1/2 + X, - Y, 1/2 + Z SFAC C H N O V UNIT 38 42 2 10 2 MERG 2 OMIT -4 4 -13 OMIT 2 0 -16 OMIT 3 3 -17 OMIT -10 0 8 OMIT -1 0 -17 TWIN BIND N1 V1 MORE -1 FMAP 2 PLAN 10 ACTA BOND $H CONF LIST 4 L.S. 44 TEMP -153.15 WGHT 0.069900 0.256800 BASF 0.08315 FVAR 1.05016 C1 1 0.943083 0.555157 0.484229 11.00000 0.03656 0.04032 = 0.04162 0.00373 -0.00024 -0.01114 AFIX 137 H1A 2 0.994767 0.578810 0.543908 11.00000 -1.50000 H1B 2 0.871725 0.652775 0.463506 11.00000 -1.50000 H1C 2 1.030390 0.539290 0.445199 11.00000 -1.50000 AFIX 0 C2 1 0.839243 0.393325 0.484344 11.00000 0.02601 0.03123 = 0.02587 -0.00142 0.00254 -0.00347 C3 1 0.866009 0.277603 0.554917 11.00000 0.02913 0.03562 = 0.02496 -0.00045 -0.00193 -0.00280 AFIX 43 H3 2 0.951917 0.303600 0.600533 11.00000 -1.20000 AFIX 0 C4 1 0.773827 0.126627 0.561992 11.00000 0.02718 0.03099 = 0.02137 0.00089 0.00080 0.00256 C5 1 0.815428 0.008933 0.639819 11.00000 0.04238 0.04136 = 0.03210 0.01087 -0.00547 -0.00200 AFIX 137 H5A 2 0.907662 0.058777 0.678796 11.00000 -1.50000 H5B 2 0.848387 -0.104927 0.619428 11.00000 -1.50000 H5C 2 0.717265 -0.003516 0.671797 11.00000 -1.50000 AFIX 0 C6 1 0.206913 0.545714 0.257031 11.00000 0.03230 0.05232 = 0.04821 0.02455 -0.00296 0.00080 AFIX 137 H6A 2 0.226583 0.532761 0.195413 11.00000 -1.50000 H6B 2 0.268572 0.646453 0.282284 11.00000 -1.50000 H6C 2 0.087306 0.562158 0.260746 11.00000 -1.50000 AFIX 0 C7 1 0.265687 0.385676 0.307163 11.00000 0.02396 0.03861 = 0.02109 0.00303 0.00013 0.00233 C8 1 0.148300 0.266409 0.332912 11.00000 0.02293 0.03688 = 0.02730 0.00309 0.00132 0.00124 AFIX 43 H8 2 0.033249 0.288550 0.316168 11.00000 -1.20000 AFIX 0 C9 1 0.191529 0.117527 0.381645 11.00000 0.02094 0.02992 = 0.02158 -0.00459 0.00315 -0.00044 C10 1 0.057030 -0.007265 0.401391 11.00000 0.02434 0.03399 = 0.04360 0.00168 0.00406 -0.00258 AFIX 137 H10A 2 -0.052686 0.042061 0.381560 11.00000 -1.50000 H10B 2 0.065328 -0.028354 0.464752 11.00000 -1.50000 H10C 2 0.070925 -0.116709 0.370709 11.00000 -1.50000 AFIX 0 C11 1 0.458018 0.571528 0.490173 11.00000 0.03244 0.02433 = 0.03245 0.00512 0.00416 -0.00283 AFIX 43 H11 2 0.508958 0.595413 0.438460 11.00000 -1.20000 AFIX 0 C12 1 0.405603 0.713928 0.537805 11.00000 0.03989 0.01999 = 0.04443 0.00181 -0.00044 -0.00179 AFIX 43 H12 2 0.420961 0.829052 0.518463 11.00000 -1.20000 AFIX 0 C13 1 0.332491 0.682415 0.612149 11.00000 0.03747 0.02658 = 0.04074 -0.00873 0.00037 0.00302 AFIX 43 H13 2 0.295746 0.775895 0.645411 11.00000 -1.20000 AFIX 0 C14 1 0.311524 0.510010 0.639599 11.00000 0.02468 0.02714 = 0.02654 -0.00868 0.00119 0.00242 C15 1 0.238280 0.468352 0.716803 11.00000 0.03019 0.04202 = 0.02788 -0.01426 0.00594 0.00313 AFIX 43 H15 2 0.197135 0.558185 0.750873 11.00000 -1.20000 AFIX 0 C16 1 0.226399 0.301060 0.742510 11.00000 0.03114 0.04477 = 0.02197 -0.00340 0.00987 -0.00197 AFIX 43 H16 2 0.177830 0.274402 0.794622 11.00000 -1.20000 AFIX 0 C17 1 0.286059 0.166768 0.691962 11.00000 0.03523 0.03196 = 0.02344 0.00191 0.00828 -0.00291 AFIX 43 H17 2 0.278524 0.050299 0.710994 11.00000 -1.20000 AFIX 0 C18 1 0.354515 0.201172 0.616094 11.00000 0.03267 0.02381 = 0.02281 -0.00080 0.00864 -0.00155 AFIX 43 H18 2 0.391708 0.108744 0.582289 11.00000 -1.20000 AFIX 0 C19 1 0.370134 0.374558 0.587740 11.00000 0.02298 0.02220 = 0.02069 -0.00433 0.00420 0.00109 N1 3 0.441724 0.407985 0.511921 11.00000 0.02802 0.02123 = 0.02268 -0.00007 0.00487 -0.00112 O1 4 0.625878 0.082792 0.324623 11.00000 0.03198 0.05275 = 0.02866 -0.01146 0.00467 0.00651 O2 4 0.731700 0.374626 0.418083 11.00000 0.02264 0.03661 = 0.02258 0.00405 0.00332 -0.00502 O3 4 0.652157 0.077210 0.507123 11.00000 0.02522 0.02777 = 0.02359 0.00216 0.00177 0.00115 O4 4 0.423408 0.370962 0.323673 11.00000 0.02478 0.03878 = 0.02151 0.00813 0.00357 0.00048 O5 4 0.339908 0.074748 0.411847 11.00000 0.02283 0.02656 = 0.02673 0.00096 0.00429 -0.00092 V1 5 0.552880 0.196655 0.398466 11.00000 0.02003 0.02964 = 0.01769 -0.00107 0.00417 0.00022 HKLF 4 REM at6_2024_a.res in Pn REM wR2 = 0.1012, GooF = S = 1.052, Restrained GooF = 1.052 for all data REM R1 = 0.0362 for 4626 Fo > 4sig(Fo) and 0.0387 for all 4882 data REM 240 parameters refined using 2 restraints END WGHT 0.0699 0.2569 REM Highest difference peak 0.681, deepest hole -0.596, 1-sigma level 0.060 Q1 1 0.4656 0.3063 0.4874 11.00000 0.05 0.68 Q2 1 0.0715 0.1867 0.8833 11.00000 0.05 0.41 Q3 1 0.5353 0.8150 0.4183 11.00000 0.05 0.38 Q4 1 0.1415 0.6871 0.8091 11.00000 0.05 0.33 Q5 1 0.5819 0.0661 0.3724 11.00000 0.05 0.31 Q6 1 0.4998 0.4232 0.4588 11.00000 0.05 0.31 Q7 1 0.3359 0.4431 0.6137 11.00000 0.05 0.30 Q8 1 0.5586 -0.0690 0.3985 11.00000 0.05 0.29 Q9 1 0.6053 0.1140 0.5609 11.00000 0.05 0.27 Q10 1 0.4229 0.3002 0.3823 11.00000 0.05 0.27 ; loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' 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 0.9431(5) 0.5552(5) 0.4842(3) 0.0398(7) Uani 1 1 d . . . . . H1A H 0.994767 0.57881 0.543908 0.06 Uiso 1 1 calc R U . . . H1B H 0.871725 0.652775 0.463506 0.06 Uiso 1 1 calc R U . . . H1C H 1.03039 0.53929 0.445199 0.06 Uiso 1 1 calc R U . . . C2 C 0.8392(4) 0.3933(4) 0.4843(2) 0.0277(6) Uani 1 1 d . . . . . C3 C 0.8660(4) 0.2776(4) 0.5549(2) 0.0303(6) Uani 1 1 d . . . . . H3 H 0.951917 0.3036 0.600533 0.036 Uiso 1 1 calc R U . . . C4 C 0.7738(4) 0.1266(4) 0.56199(18) 0.0267(5) Uani 1 1 d . . . . . C5 C 0.8154(6) 0.0089(6) 0.6398(3) 0.0393(8) Uani 1 1 d . . . . . H5A H 0.907662 0.058777 0.678796 0.059 Uiso 1 1 calc R U . . . H5B H 0.848387 -0.104927 0.619428 0.059 Uiso 1 1 calc R U . . . H5C H 0.717265 -0.003516 0.671797 0.059 Uiso 1 1 calc R U . . . C6 C 0.2069(5) 0.5457(5) 0.2570(3) 0.0448(9) Uani 1 1 d . . . . . H6A H 0.226583 0.532761 0.195413 0.067 Uiso 1 1 calc R U . . . H6B H 0.268572 0.646453 0.282284 0.067 Uiso 1 1 calc R U . . . H6C H 0.087306 0.562158 0.260746 0.067 Uiso 1 1 calc R U . . . C7 C 0.2657(4) 0.3857(5) 0.3072(2) 0.0281(6) Uani 1 1 d . . . . . C8 C 0.1483(4) 0.2664(4) 0.3329(2) 0.0291(6) Uani 1 1 d . . . . . H8 H 0.033249 0.28855 0.316168 0.035 Uiso 1 1 calc R U . . . C9 C 0.1915(3) 0.1175(4) 0.38164(18) 0.0241(5) Uani 1 1 d . . . . . C10 C 0.0570(5) -0.0073(4) 0.4014(3) 0.0340(5) Uani 1 1 d . . . . . H10A H -0.052686 0.042061 0.38156 0.051 Uiso 1 1 calc R U . . . H10B H 0.065328 -0.028354 0.464752 0.051 Uiso 1 1 calc R U . . . H10C H 0.070925 -0.116709 0.370709 0.051 Uiso 1 1 calc R U . . . C11 C 0.4580(4) 0.5715(4) 0.4902(2) 0.0297(6) Uani 1 1 d . . . . . H11 H 0.508958 0.595413 0.43846 0.036 Uiso 1 1 calc R U . . . C12 C 0.4056(5) 0.7139(4) 0.5378(3) 0.0351(8) Uani 1 1 d . . . . . H12 H 0.420961 0.829052 0.518463 0.042 Uiso 1 1 calc R U . . . C13 C 0.3325(5) 0.6824(4) 0.6121(3) 0.0352(7) Uani 1 1 d . . . . . H13 H 0.295746 0.775895 0.645411 0.042 Uiso 1 1 calc R U . . . C14 C 0.3115(4) 0.5100(4) 0.6396(2) 0.0262(6) Uani 1 1 d . . . . . C15 C 0.2383(4) 0.4684(5) 0.7168(2) 0.0332(6) Uani 1 1 d . . . . . H15 H 0.197135 0.558185 0.750873 0.04 Uiso 1 1 calc R U . . . C16 C 0.2264(5) 0.3011(5) 0.7425(2) 0.0321(8) Uani 1 1 d . . . . . H16 H 0.17783 0.274402 0.794622 0.039 Uiso 1 1 calc R U . . . C17 C 0.2861(4) 0.1668(4) 0.6920(2) 0.0298(6) Uani 1 1 d . . . . . H17 H 0.278524 0.050299 0.710994 0.036 Uiso 1 1 calc R U . . . C18 C 0.3545(4) 0.2012(3) 0.6161(2) 0.0260(6) Uani 1 1 d . . . . . H18 H 0.391708 0.108744 0.582289 0.031 Uiso 1 1 calc R U . . . C19 C 0.3701(4) 0.3746(3) 0.58774(18) 0.0218(5) Uani 1 1 d . . . . . N1 N 0.4417(3) 0.4080(3) 0.51192(16) 0.0238(4) Uani 1 1 d . . . . . O1 O 0.6259(3) 0.0828(3) 0.32462(16) 0.0377(5) Uani 1 1 d . . . . . O2 O 0.7317(3) 0.3746(3) 0.41808(14) 0.0272(4) Uani 1 1 d . . . . . O3 O 0.6522(3) 0.0772(3) 0.50712(14) 0.0256(4) Uani 1 1 d . . . . . O4 O 0.4234(3) 0.3710(3) 0.32367(13) 0.0283(4) Uani 1 1 d . . . . . O5 O 0.3399(3) 0.0747(3) 0.41185(14) 0.0253(4) Uani 1 1 d . . . . . V1 V 0.55288(5) 0.19665(5) 0.39847(3) 0.02230(12) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0366(17) 0.0403(17) 0.0416(18) 0.0037(14) -0.0002(15) -0.0111(14) C2 0.0260(15) 0.0312(15) 0.0259(14) -0.0014(11) 0.0025(12) -0.0035(11) C3 0.0291(15) 0.0356(15) 0.0250(13) -0.0004(11) -0.0019(11) -0.0028(11) C4 0.0272(13) 0.0310(13) 0.0214(12) 0.0009(10) 0.0008(10) 0.0026(11) C5 0.0424(18) 0.0414(16) 0.0321(17) 0.0109(13) -0.0055(14) -0.0020(13) C6 0.0323(17) 0.052(2) 0.048(2) 0.0245(17) -0.0030(15) 0.0008(15) C7 0.0240(14) 0.0386(17) 0.0211(13) 0.0030(11) 0.0001(11) 0.0023(12) C8 0.0229(13) 0.0369(14) 0.0273(14) 0.0031(12) 0.0013(11) 0.0012(11) C9 0.0209(12) 0.0299(13) 0.0216(11) -0.0046(9) 0.0032(9) -0.0004(9) C10 0.0243(12) 0.0340(12) 0.0436(14) 0.0017(16) 0.0041(10) -0.0026(15) C11 0.0324(15) 0.0243(13) 0.0325(15) 0.0051(11) 0.0042(12) -0.0028(11) C12 0.0399(19) 0.0200(13) 0.044(2) 0.0018(12) -0.0004(15) -0.0018(12) C13 0.0375(17) 0.0266(14) 0.0407(18) -0.0087(12) 0.0004(14) 0.0030(12) C14 0.0247(12) 0.0271(12) 0.0265(14) -0.0087(10) 0.0012(10) 0.0024(9) C15 0.0302(14) 0.0420(16) 0.0279(14) -0.0143(13) 0.0059(11) 0.0031(12) C16 0.0311(17) 0.0448(19) 0.0220(14) -0.0034(11) 0.0099(13) -0.0020(12) C17 0.0352(16) 0.0320(14) 0.0234(13) 0.0019(11) 0.0083(12) -0.0029(12) C18 0.0327(15) 0.0238(12) 0.0228(12) -0.0008(9) 0.0086(11) -0.0016(10) C19 0.0230(12) 0.0222(11) 0.0207(11) -0.0043(10) 0.0042(9) 0.0011(10) N1 0.0280(11) 0.0212(10) 0.0227(10) -0.0001(8) 0.0049(9) -0.0011(9) O1 0.0320(12) 0.0528(14) 0.0287(11) -0.0115(10) 0.0047(9) 0.0065(10) O2 0.0226(9) 0.0366(10) 0.0226(9) 0.0040(8) 0.0033(8) -0.0050(8) O3 0.0252(10) 0.0278(9) 0.0236(9) 0.0022(7) 0.0018(7) 0.0011(7) O4 0.0248(10) 0.0388(11) 0.0215(9) 0.0081(8) 0.0036(8) 0.0005(8) O5 0.0228(9) 0.0266(9) 0.0267(9) 0.0010(7) 0.0043(7) -0.0009(7) V1 0.02003(19) 0.0296(2) 0.01769(18) -0.00107(19) 0.00417(13) 0.00022(19) 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 0 -1 0.0670 3 1 2 0.0740 0 0 -1 0.0930 0 0 1 0.0890 1 2 2 0.0460 1 -3 1 0.0710 -1 2 -2 0.0720 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 125.4(3) . . ? O2 C2 C1 115.1(3) . . ? C3 C2 C1 119.5(3) . . ? C4 C3 C2 123.8(3) . . ? C4 C3 H3 118.1 . . ? C2 C3 H3 118.1 . . ? O3 C4 C3 125.2(3) . . ? O3 C4 C5 115.4(3) . . ? C3 C4 C5 119.5(3) . . ? 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 H6A 109.5 . . ? C7 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C7 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O4 C7 C8 124.9(3) . . ? O4 C7 C6 115.2(3) . . ? C8 C7 C6 119.8(3) . . ? C9 C8 C7 123.6(3) . . ? C9 C8 H8 118.2 . . ? C7 C8 H8 118.2 . . ? O5 C9 C8 125.2(3) . . ? O5 C9 C10 115.3(3) . . ? C8 C9 C10 119.5(3) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 C12 125.0(3) . . ? N1 C11 H11 117.5 . . ? C12 C11 H11 117.5 . . ? C13 C12 C11 118.4(3) . . ? C13 C12 H12 120.8 . . ? C11 C12 H12 120.8 . . ? C12 C13 C14 119.7(3) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C13 C14 C15 122.5(3) . . ? C13 C14 C19 117.9(3) . . ? C15 C14 C19 119.5(3) . . ? C16 C15 C14 120.5(3) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C17 120.1(3) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C18 C17 C16 121.2(3) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C17 C18 C19 120.1(3) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? N1 C19 C18 119.7(2) . . ? N1 C19 C14 121.9(2) . . ? C18 C19 C14 118.5(3) . . ? C11 N1 C19 117.1(2) . . ? C11 N1 V1 112.32(19) . . ? C19 N1 V1 130.54(17) . . ? C2 O2 V1 128.2(2) . . ? C4 O3 V1 128.33(19) . . ? C7 O4 V1 128.6(2) . . ? C9 O5 V1 128.63(19) . . ? O1 V1 O5 101.63(12) . . ? O1 V1 O4 100.09(12) . . ? O5 V1 O4 88.63(9) . . ? O1 V1 O2 99.84(12) . . ? O5 V1 O2 158.52(9) . . ? O4 V1 O2 86.83(9) . . ? O1 V1 O3 101.08(12) . . ? O5 V1 O3 88.07(9) . . ? O4 V1 O3 158.81(9) . . ? O2 V1 O3 88.63(9) . . ? O1 V1 N1 174.80(12) . . ? O5 V1 N1 82.22(8) . . ? O4 V1 N1 76.37(8) . . ? O2 V1 N1 76.30(8) . . ? O3 V1 N1 82.45(8) . . ? 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 1.505(5) . ? C1 H1A 0.98 . ? C1 H1B 0.98 . ? C1 H1C 0.98 . ? C2 O2 1.269(4) . ? C2 C3 1.402(5) . ? C3 C4 1.394(4) . ? C3 H3 0.95 . ? C4 O3 1.278(4) . ? C4 C5 1.508(4) . ? C5 H5A 0.98 . ? C5 H5B 0.98 . ? C5 H5C 0.98 . ? C6 C7 1.505(5) . ? C6 H6A 0.98 . ? C6 H6B 0.98 . ? C6 H6C 0.98 . ? C7 O4 1.273(4) . ? C7 C8 1.408(5) . ? C8 C9 1.395(4) . ? C8 H8 0.95 . ? C9 O5 1.277(4) . ? C9 C10 1.506(4) . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C10 H10C 0.98 . ? C11 N1 1.317(4) . ? C11 C12 1.411(5) . ? C11 H11 0.95 . ? C12 C13 1.361(6) . ? C12 H12 0.95 . ? C13 C14 1.413(5) . ? C13 H13 0.95 . ? C14 C15 1.416(4) . ? C14 C19 1.426(4) . ? C15 C16 1.358(5) . ? C15 H15 0.95 . ? C16 C17 1.411(5) . ? C16 H16 0.95 . ? C17 C18 1.367(4) . ? C17 H17 0.95 . ? C18 C19 1.418(4) . ? C18 H18 0.95 . ? C19 N1 1.378(3) . ? N1 V1 2.615(2) . ? O1 V1 1.596(2) . ? O2 V1 1.991(2) . ? O3 V1 1.994(2) . ? O4 V1 1.989(2) . ? O5 V1 1.988(2) . ? 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 -1.4(5) . . . . ? C1 C2 C3 C4 178.5(3) . . . . ? C2 C3 C4 O3 -1.9(5) . . . . ? C2 C3 C4 C5 178.7(3) . . . . ? O4 C7 C8 C9 1.2(5) . . . . ? C6 C7 C8 C9 -178.1(3) . . . . ? C7 C8 C9 O5 3.1(5) . . . . ? C7 C8 C9 C10 -176.5(3) . . . . ? N1 C11 C12 C13 0.1(6) . . . . ? C11 C12 C13 C14 0.2(6) . . . . ? C12 C13 C14 C15 179.2(4) . . . . ? C12 C13 C14 C19 0.5(5) . . . . ? C13 C14 C15 C16 -177.5(4) . . . . ? C19 C14 C15 C16 1.2(5) . . . . ? C14 C15 C16 C17 -0.5(6) . . . . ? C15 C16 C17 C18 -0.9(6) . . . . ? C16 C17 C18 C19 1.4(5) . . . . ? C17 C18 C19 N1 179.0(3) . . . . ? C17 C18 C19 C14 -0.6(5) . . . . ? C13 C14 C19 N1 -1.5(5) . . . . ? C15 C14 C19 N1 179.7(3) . . . . ? C13 C14 C19 C18 178.1(3) . . . . ? C15 C14 C19 C18 -0.7(5) . . . . ? C12 C11 N1 C19 -1.0(5) . . . . ? C12 C11 N1 V1 178.5(3) . . . . ? C18 C19 N1 C11 -177.9(3) . . . . ? C14 C19 N1 C11 1.7(4) . . . . ? C18 C19 N1 V1 2.8(4) . . . . ? C14 C19 N1 V1 -177.7(2) . . . . ? C3 C2 O2 V1 7.6(5) . . . . ? C1 C2 O2 V1 -172.2(2) . . . . ? C3 C4 O3 V1 -1.5(4) . . . . ? C5 C4 O3 V1 178.0(2) . . . . ? C8 C7 O4 V1 -6.8(5) . . . . ? C6 C7 O4 V1 172.6(3) . . . . ? C8 C9 O5 V1 -1.5(4) . . . . ? C10 C9 O5 V1 178.1(2) . . . . ?