#------------------------------------------------------------------------------ #$Date: 2026-06-02 23:54:29 +0100 (Tue, 02 Jun 2026) $ #$Revision: 306170 $ #$URL: svn://www.crystallography.net/cod/cif/7/72/10/7721071.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_7721071 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 ; cis-bis(acetylacetonato-k2O,O')oxido(isoquinoline-kN)vanadium(IV) ; _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 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 2025-06-13 _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 108.51(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.222(2) _cell_length_b 20.454(8) _cell_length_c 11.506(4) _cell_measurement_reflns_used 5317 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 25.78 _cell_measurement_theta_min 2.05 _cell_volume 1834.9(11) _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 0.986 _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 0.0597 _diffrn_reflns_av_unetI/netI 0.0395 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.986 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 27562 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.986 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.295 _diffrn_reflns_theta_min 2.613 _diffrn_source 'GeniX Mo, 0.05 x 0.05 mm2 microfocus' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.57 _exptl_absorpt_correction_type none _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 820 _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.484 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.079 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 239 _refine_ls_number_reflns 4955 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.029 _refine_ls_R_factor_all 0.0685 _refine_ls_R_factor_gt 0.0445 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0669P)^2^+0.4880P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.108 _refine_ls_wR_factor_ref 0.1175 _reflns_Friedel_coverage 0 _reflns_number_gt 3629 _reflns_number_total 4955 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6dt01029f2.cif _cod_data_source_block wd7 _cod_original_cell_volume 1834.8(11) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7721071 _shelx_shelxl_version_number 2018/3 _shelx_res_file ; TITL wd7_a.res in P2(1)/c shelx.res created by SHELXL-2018/3 at 17:47:46 on 13-Jun-2025 CELL 0.71073 8.2216 20.4544 11.5056 90.000 108.509 90.000 ZERR 4.00 0.0023 0.0076 0.0039 0.000 0.023 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O V UNIT 76 84 4 20 4 MERG 2 MORE -1 FMAP 2 53 53 PLAN 10 ACTA BOND $H CONF LIST 4 L.S. 54 TEMP -153.15 WGHT 0.066900 0.488000 FVAR 0.40387 C1 1 0.947332 0.231984 0.687384 11.00000 0.04102 0.02742 = 0.04125 -0.00091 0.01697 0.00286 AFIX 137 H1A 2 1.063729 0.226009 0.744141 11.00000 -1.50000 H1B 2 0.936823 0.209679 0.609955 11.00000 -1.50000 H1C 2 0.864366 0.213509 0.723478 11.00000 -1.50000 AFIX 0 C2 1 0.912273 0.303497 0.663795 11.00000 0.01610 0.02427 = 0.03017 -0.00369 0.00882 -0.00034 C3 1 0.900458 0.329560 0.549638 11.00000 0.02567 0.02819 = 0.02651 -0.00732 0.01094 -0.00203 AFIX 43 H3 2 0.908556 0.300066 0.487929 11.00000 -1.20000 AFIX 0 C4 1 0.877698 0.395498 0.518955 11.00000 0.01862 0.03007 = 0.02001 -0.00393 0.00789 -0.00375 C5 1 0.878808 0.418316 0.395174 11.00000 0.03768 0.03271 = 0.02236 -0.00523 0.01450 -0.00305 AFIX 137 H5A 2 0.763507 0.432906 0.347155 11.00000 -1.50000 H5B 2 0.914000 0.382233 0.352449 11.00000 -1.50000 H5C 2 0.959642 0.454703 0.405127 11.00000 -1.50000 AFIX 0 C6 1 0.681353 0.418675 1.076588 11.00000 0.03167 0.03475 = 0.02150 0.00033 0.01352 -0.00314 AFIX 137 H6A 2 0.670915 0.373598 1.102204 11.00000 -1.50000 H6B 2 0.589434 0.445340 1.089328 11.00000 -1.50000 H6C 2 0.792826 0.436490 1.125246 11.00000 -1.50000 AFIX 0 C7 1 0.667420 0.419586 0.943618 11.00000 0.02526 0.02116 = 0.02126 -0.00027 0.01180 -0.00101 C8 1 0.506270 0.420905 0.855537 11.00000 0.02218 0.03083 = 0.02544 -0.00034 0.01300 -0.00220 AFIX 43 H8 2 0.409320 0.426347 0.882618 11.00000 -1.20000 AFIX 0 C9 1 0.477701 0.414734 0.729579 11.00000 0.02086 0.02022 = 0.02449 0.00120 0.00941 -0.00028 C10 1 0.296225 0.409854 0.646153 11.00000 0.02014 0.04219 = 0.03113 -0.00162 0.00887 -0.00045 AFIX 137 H10A 2 0.273196 0.445324 0.585836 11.00000 -1.50000 H10B 2 0.217611 0.413384 0.694486 11.00000 -1.50000 H10C 2 0.279254 0.367665 0.603610 11.00000 -1.50000 AFIX 0 C11 1 0.648329 0.552885 0.647913 11.00000 0.02374 0.02836 = 0.01769 0.00104 0.00675 -0.00152 AFIX 43 H11 2 0.626064 0.526410 0.576720 11.00000 -1.20000 AFIX 0 C12 1 0.567724 0.611500 0.637811 11.00000 0.02360 0.03074 = 0.02080 0.00469 0.00474 0.00029 AFIX 43 H12 2 0.493435 0.625769 0.560626 11.00000 -1.20000 AFIX 0 C13 1 0.594971 0.651188 0.742822 11.00000 0.01992 0.02652 = 0.02464 0.00473 0.00908 -0.00145 C14 1 0.508991 0.711216 0.743352 11.00000 0.02660 0.02684 = 0.03149 0.00535 0.00878 0.00212 AFIX 43 H14 2 0.429452 0.727290 0.669666 11.00000 -1.20000 AFIX 0 C15 1 0.540228 0.745980 0.849511 11.00000 0.03214 0.02262 = 0.04253 0.00153 0.01505 0.00267 AFIX 43 H15 2 0.480305 0.785710 0.849337 11.00000 -1.20000 AFIX 0 C16 1 0.660130 0.723708 0.959276 11.00000 0.03520 0.02614 = 0.03166 -0.00521 0.01332 -0.00150 AFIX 43 H16 2 0.681372 0.748918 1.031931 11.00000 -1.20000 AFIX 0 C17 1 0.746516 0.666080 0.962473 11.00000 0.02831 0.02671 = 0.02397 -0.00129 0.00903 -0.00058 AFIX 43 H17 2 0.827768 0.651485 1.036699 11.00000 -1.20000 AFIX 0 C18 1 0.713481 0.628524 0.854092 11.00000 0.01931 0.02377 = 0.02263 0.00064 0.00900 -0.00204 C19 1 0.793193 0.567193 0.854287 11.00000 0.01954 0.02390 = 0.02079 0.00112 0.00793 -0.00077 AFIX 43 H19 2 0.873772 0.552161 0.928442 11.00000 -1.20000 AFIX 0 N1 3 0.760256 0.529932 0.755630 11.00000 0.01773 0.02502 = 0.01878 -0.00034 0.00687 -0.00149 O1 4 1.055863 0.454820 0.830063 11.00000 0.02055 0.03103 = 0.02418 -0.00113 0.00905 0.00123 O2 4 0.898909 0.336001 0.754675 11.00000 0.02695 0.02483 = 0.02518 0.00021 0.01080 0.00292 O3 4 0.855656 0.440177 0.589950 11.00000 0.02200 0.02477 = 0.02028 -0.00147 0.01025 -0.00076 O4 4 0.595977 0.411327 0.680341 11.00000 0.01847 0.02734 = 0.01970 -0.00222 0.00780 -0.00177 O5 4 0.809791 0.417889 0.920257 11.00000 0.02125 0.02744 = 0.01860 0.00011 0.00842 0.00010 V1 5 0.861941 0.432245 0.764565 11.00000 0.01709 0.02274 = 0.01749 -0.00134 0.00744 -0.00031 HKLF 4 REM wd7_a.res in P2(1)/c REM wR2 = 0.1175, GooF = S = 1.029, Restrained GooF = 1.029 for all data REM R1 = 0.0445 for 3629 Fo > 4sig(Fo) and 0.0685 for all 4955 data REM 239 parameters refined using 0 restraints END WGHT 0.0669 0.4880 REM Highest difference peak 0.484, deepest hole -0.389, 1-sigma level 0.079 Q1 1 0.8535 0.4280 0.6603 11.00000 0.05 0.48 Q2 1 0.7000 0.4257 0.7265 11.00000 0.05 0.47 Q3 1 0.7804 0.4245 0.8205 11.00000 0.05 0.47 Q4 1 0.8718 0.3844 0.7262 11.00000 0.05 0.46 Q5 1 0.8046 0.4604 0.7993 11.00000 0.05 0.40 Q6 1 0.8183 0.4637 0.6984 11.00000 0.05 0.38 Q7 1 0.8214 0.4356 0.8609 11.00000 0.05 0.38 Q8 1 0.8542 0.3983 0.4479 11.00000 0.05 0.37 Q9 1 0.8461 0.4185 0.5473 11.00000 0.05 0.37 Q10 1 0.8560 0.3949 0.8209 11.00000 0.05 0.37 ; 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' 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 0.9473(3) 0.23198(11) 0.6874(2) 0.0356(5) Uani 1 1 d . . . . . H1A H 1.063729 0.226009 0.744141 0.053 Uiso 1 1 calc R U . . . H1B H 0.936823 0.209679 0.609955 0.053 Uiso 1 1 calc R U . . . H1C H 0.864366 0.213509 0.723478 0.053 Uiso 1 1 calc R U . . . C2 C 0.9123(2) 0.30350(10) 0.66380(19) 0.0232(4) Uani 1 1 d . . . . . C3 C 0.9005(3) 0.32956(10) 0.54964(19) 0.0262(4) Uani 1 1 d . . . . . H3 H 0.908556 0.300066 0.487929 0.031 Uiso 1 1 calc R U . . . C4 C 0.8777(2) 0.39550(10) 0.51895(18) 0.0225(4) Uani 1 1 d . . . . . C5 C 0.8788(3) 0.41832(11) 0.39517(19) 0.0297(5) Uani 1 1 d . . . . . H5A H 0.763507 0.432906 0.347155 0.045 Uiso 1 1 calc R U . . . H5B H 0.914 0.382233 0.352449 0.045 Uiso 1 1 calc R U . . . H5C H 0.959642 0.454703 0.405127 0.045 Uiso 1 1 calc R U . . . C6 C 0.6814(3) 0.41867(11) 1.07659(18) 0.0281(5) Uani 1 1 d . . . . . H6A H 0.670915 0.373598 1.102204 0.042 Uiso 1 1 calc R U . . . H6B H 0.589434 0.44534 1.089328 0.042 Uiso 1 1 calc R U . . . H6C H 0.792826 0.43649 1.125246 0.042 Uiso 1 1 calc R U . . . C7 C 0.6674(3) 0.41959(9) 0.94362(18) 0.0215(4) Uani 1 1 d . . . . . C8 C 0.5063(3) 0.42091(10) 0.85554(19) 0.0249(4) Uani 1 1 d . . . . . H8 H 0.40932 0.426347 0.882618 0.03 Uiso 1 1 calc R U . . . C9 C 0.4777(2) 0.41473(10) 0.72958(18) 0.0213(4) Uani 1 1 d . . . . . C10 C 0.2962(3) 0.40985(12) 0.6462(2) 0.0310(5) Uani 1 1 d . . . . . H10A H 0.273196 0.445324 0.585836 0.046 Uiso 1 1 calc R U . . . H10B H 0.217611 0.413384 0.694486 0.046 Uiso 1 1 calc R U . . . H10C H 0.279254 0.367665 0.60361 0.046 Uiso 1 1 calc R U . . . C11 C 0.6483(3) 0.55288(10) 0.64791(17) 0.0232(4) Uani 1 1 d . . . . . H11 H 0.626064 0.52641 0.57672 0.028 Uiso 1 1 calc R U . . . C12 C 0.5677(3) 0.61150(10) 0.63781(18) 0.0256(4) Uani 1 1 d . . . . . H12 H 0.493435 0.625769 0.560626 0.031 Uiso 1 1 calc R U . . . C13 C 0.5950(2) 0.65119(10) 0.74282(18) 0.0232(4) Uani 1 1 d . . . . . C14 C 0.5090(3) 0.71122(11) 0.7434(2) 0.0284(4) Uani 1 1 d . . . . . H14 H 0.429452 0.72729 0.669666 0.034 Uiso 1 1 calc R U . . . C15 C 0.5402(3) 0.74598(11) 0.8495(2) 0.0317(5) Uani 1 1 d . . . . . H15 H 0.480305 0.78571 0.849337 0.038 Uiso 1 1 calc R U . . . C16 C 0.6601(3) 0.72371(11) 0.9593(2) 0.0304(5) Uani 1 1 d . . . . . H16 H 0.681372 0.748918 1.031931 0.036 Uiso 1 1 calc R U . . . C17 C 0.7465(3) 0.66608(10) 0.96247(19) 0.0262(4) Uani 1 1 d . . . . . H17 H 0.827768 0.651485 1.036699 0.031 Uiso 1 1 calc R U . . . C18 C 0.7135(2) 0.62852(10) 0.85409(18) 0.0214(4) Uani 1 1 d . . . . . C19 C 0.7932(2) 0.56719(9) 0.85429(17) 0.0210(4) Uani 1 1 d . . . . . H19 H 0.873772 0.552161 0.928442 0.025 Uiso 1 1 calc R U . . . N1 N 0.76026(19) 0.52993(8) 0.75563(14) 0.0203(3) Uani 1 1 d . . . . . O1 O 1.05586(17) 0.45482(7) 0.83006(13) 0.0248(3) Uani 1 1 d . . . . . O2 O 0.89891(18) 0.33600(7) 0.75468(13) 0.0251(3) Uani 1 1 d . . . . . O3 O 0.85566(17) 0.44018(7) 0.58995(12) 0.0215(3) Uani 1 1 d . . . . . O4 O 0.59598(17) 0.41133(7) 0.68034(12) 0.0214(3) Uani 1 1 d . . . . . O5 O 0.80979(17) 0.41789(7) 0.92026(12) 0.0219(3) Uani 1 1 d . . . . . V1 V 0.86194(4) 0.43225(2) 0.76456(3) 0.01865(10) 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 0.0410(13) 0.0274(11) 0.0413(13) -0.0009(10) 0.0170(11) 0.0029(10) C2 0.0161(9) 0.0243(10) 0.0302(10) -0.0037(8) 0.0088(8) -0.0003(7) C3 0.0257(10) 0.0282(11) 0.0265(10) -0.0073(8) 0.0109(8) -0.0020(8) C4 0.0186(9) 0.0301(11) 0.0200(9) -0.0039(8) 0.0079(7) -0.0038(8) C5 0.0377(12) 0.0327(12) 0.0224(10) -0.0052(9) 0.0145(9) -0.0030(9) C6 0.0317(11) 0.0348(12) 0.0215(10) 0.0003(8) 0.0135(8) -0.0031(9) C7 0.0253(10) 0.0212(10) 0.0213(9) -0.0003(7) 0.0118(8) -0.0010(7) C8 0.0222(10) 0.0308(11) 0.0254(10) -0.0003(8) 0.0130(8) -0.0022(8) C9 0.0209(9) 0.0202(9) 0.0245(9) 0.0012(8) 0.0094(8) -0.0003(7) C10 0.0201(10) 0.0422(13) 0.0311(11) -0.0016(10) 0.0089(8) -0.0005(9) C11 0.0237(10) 0.0284(11) 0.0177(9) 0.0010(8) 0.0067(7) -0.0015(8) C12 0.0236(10) 0.0307(11) 0.0208(9) 0.0047(8) 0.0047(8) 0.0003(8) C13 0.0199(9) 0.0265(10) 0.0246(9) 0.0047(8) 0.0091(8) -0.0015(7) C14 0.0266(11) 0.0268(11) 0.0315(11) 0.0054(9) 0.0088(9) 0.0021(8) C15 0.0321(12) 0.0226(10) 0.0425(13) 0.0015(9) 0.0151(10) 0.0027(8) C16 0.0352(12) 0.0261(11) 0.0317(11) -0.0052(9) 0.0133(9) -0.0015(9) C17 0.0283(10) 0.0267(10) 0.0240(10) -0.0013(8) 0.0090(8) -0.0006(8) C18 0.0193(9) 0.0238(10) 0.0226(9) 0.0006(8) 0.0090(7) -0.0020(7) C19 0.0195(9) 0.0239(9) 0.0208(9) 0.0011(8) 0.0079(7) -0.0008(7) N1 0.0177(8) 0.0250(9) 0.0188(8) -0.0003(6) 0.0069(6) -0.0015(6) O1 0.0206(7) 0.0310(8) 0.0242(7) -0.0011(6) 0.0090(6) 0.0012(6) O2 0.0270(7) 0.0248(7) 0.0252(7) 0.0002(6) 0.0108(6) 0.0029(6) O3 0.0220(7) 0.0248(7) 0.0203(6) -0.0015(5) 0.0102(5) -0.0008(5) O4 0.0185(7) 0.0273(7) 0.0197(6) -0.0022(6) 0.0078(5) -0.0018(5) O5 0.0213(7) 0.0274(7) 0.0186(6) 0.0001(5) 0.0084(5) 0.0001(5) V1 0.01709(16) 0.02274(18) 0.01749(16) -0.00134(13) 0.00744(12) -0.00031(13) 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_ _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 125.22(19) . . ? O2 C2 C1 115.01(19) . . ? C3 C2 C1 119.76(19) . . ? C4 C3 C2 125.03(19) . . ? C4 C3 H3 117.5 . . ? C2 C3 H3 117.5 . . ? O3 C4 C3 124.51(19) . . ? O3 C4 C5 115.42(18) . . ? C3 C4 C5 120.07(18) . . ? 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 . . ? O5 C7 C8 124.77(18) . . ? O5 C7 C6 115.79(18) . . ? C8 C7 C6 119.43(18) . . ? C7 C8 C9 124.17(19) . . ? C7 C8 H8 117.9 . . ? C9 C8 H8 117.9 . . ? O4 C9 C8 124.43(18) . . ? O4 C9 C10 117.18(18) . . ? C8 C9 C10 118.37(18) . . ? 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 . . ? C12 C11 N1 123.33(18) . . ? C12 C11 H11 118.3 . . ? N1 C11 H11 118.3 . . ? C11 C12 C13 119.59(18) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C12 C13 C14 123.86(19) . . ? C12 C13 C18 117.45(19) . . ? C14 C13 C18 118.67(19) . . ? C15 C14 C13 120.2(2) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 120.9(2) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C17 C16 C15 120.8(2) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C16 C17 C18 119.4(2) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C19 C18 C17 121.36(18) . . ? C19 C18 C13 118.45(18) . . ? C17 C18 C13 120.17(19) . . ? N1 C19 C18 122.77(18) . . ? N1 C19 H19 118.6 . . ? C18 C19 H19 118.6 . . ? C19 N1 C11 118.33(17) . . ? C19 N1 V1 121.52(13) . . ? C11 N1 V1 119.96(13) . . ? C2 O2 V1 127.95(13) . . ? C4 O3 V1 128.40(13) . . ? C9 O4 V1 127.15(13) . . ? C7 O5 V1 131.01(13) . . ? O1 V1 O5 94.92(7) . . ? O1 V1 O3 98.85(7) . . ? O5 V1 O3 166.23(6) . . ? O1 V1 O2 99.45(7) . . ? O5 V1 O2 89.20(6) . . ? O3 V1 O2 88.78(6) . . ? O1 V1 O4 174.52(7) . . ? O5 V1 O4 84.08(6) . . ? O3 V1 O4 82.19(6) . . ? O2 V1 O4 85.94(6) . . ? O1 V1 N1 93.92(7) . . ? O5 V1 N1 89.35(6) . . ? O3 V1 N1 89.48(6) . . ? O2 V1 N1 166.63(6) . . ? O4 V1 N1 80.69(6) . . ? 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(3) . ? C1 H1A 0.98 . ? C1 H1B 0.98 . ? C1 H1C 0.98 . ? C2 O2 1.273(2) . ? C2 C3 1.392(3) . ? C3 C4 1.392(3) . ? C3 H3 0.95 . ? C4 O3 1.276(2) . ? C4 C5 1.501(3) . ? C5 H5A 0.98 . ? C5 H5B 0.98 . ? C5 H5C 0.98 . ? C6 C7 1.498(3) . ? C6 H6A 0.98 . ? C6 H6B 0.98 . ? C6 H6C 0.98 . ? C7 O5 1.282(2) . ? C7 C8 1.389(3) . ? C8 C9 1.398(3) . ? C8 H8 0.95 . ? C9 O4 1.273(2) . ? C9 C10 1.499(3) . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C10 H10C 0.98 . ? C11 C12 1.357(3) . ? C11 N1 1.371(2) . ? C11 H11 0.95 . ? C12 C13 1.413(3) . ? C12 H12 0.95 . ? C13 C14 1.418(3) . ? C13 C18 1.418(3) . ? C14 C15 1.365(3) . ? C14 H14 0.95 . ? C15 C16 1.408(3) . ? C15 H15 0.95 . ? C16 C17 1.371(3) . ? C16 H16 0.95 . ? C17 C18 1.416(3) . ? C17 H17 0.95 . ? C18 C19 1.415(3) . ? C19 N1 1.322(2) . ? C19 H19 0.95 . ? N1 V1 2.1558(18) . ? O1 V1 1.6001(15) . ? O2 V1 2.0007(16) . ? O3 V1 1.9998(15) . ? O4 V1 2.1350(15) . ? O5 V1 1.9916(15) . ? 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 2.2(3) . . . . ? C1 C2 C3 C4 -176.4(2) . . . . ? C2 C3 C4 O3 -3.9(3) . . . . ? C2 C3 C4 C5 175.84(19) . . . . ? O5 C7 C8 C9 5.9(3) . . . . ? C6 C7 C8 C9 -172.78(19) . . . . ? C7 C8 C9 O4 -4.6(3) . . . . ? C7 C8 C9 C10 173.6(2) . . . . ? N1 C11 C12 C13 -1.6(3) . . . . ? C11 C12 C13 C14 -176.0(2) . . . . ? C11 C12 C13 C18 2.9(3) . . . . ? C12 C13 C14 C15 178.6(2) . . . . ? C18 C13 C14 C15 -0.2(3) . . . . ? C13 C14 C15 C16 1.3(3) . . . . ? C14 C15 C16 C17 -1.0(3) . . . . ? C15 C16 C17 C18 -0.4(3) . . . . ? C16 C17 C18 C19 -176.84(19) . . . . ? C16 C17 C18 C13 1.4(3) . . . . ? C12 C13 C18 C19 -1.7(3) . . . . ? C14 C13 C18 C19 177.21(18) . . . . ? C12 C13 C18 C17 179.94(18) . . . . ? C14 C13 C18 C17 -1.1(3) . . . . ? C17 C18 C19 N1 177.48(18) . . . . ? C13 C18 C19 N1 -0.8(3) . . . . ? C18 C19 N1 C11 2.2(3) . . . . ? C18 C19 N1 V1 -172.85(14) . . . . ? C12 C11 N1 C19 -1.0(3) . . . . ? C12 C11 N1 V1 174.15(16) . . . . ? C3 C2 O2 V1 -1.2(3) . . . . ? C1 C2 O2 V1 177.43(14) . . . . ? C3 C4 O3 V1 4.4(3) . . . . ? C5 C4 O3 V1 -175.33(13) . . . . ? C8 C9 O4 V1 -12.9(3) . . . . ? C10 C9 O4 V1 168.86(14) . . . . ? C8 C7 O5 V1 12.4(3) . . . . ? C6 C7 O5 V1 -168.89(13) . . . . ?