# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 186/1911 data_9/02385B _audit_creation_method 'SHELXL97 and manual editing' # 1. SUBMISSION DETAILS _publ_contact_author_name 'Augusto S. Ceccato' _publ_contact_author_address ; Depto. Qu\'imica - UFSC 88040 - 900 Florian\'opolis, SC Brazil ; _publ_contact_author_email ceccato@qmc.ufsc.br _publ_contact_author_fax '55(48)3316888' _publ_contact_author_phone '55(48)3316826' _publ_contact_letter ; Please consider this CIF as a deposition of crystallographic data of the structure included in the submitted paper quoted as 9/02385B. ; _publ_requested_coeditor_name ? _publ_requested_journal ; J. of the Chemical Society, Dalton Transactions ; # 3. TITLE AND AUTHOR LIST _publ_section_title ; Magneto-structural correlation for binuclear octahedral vanadium(IV)-oxo complexes. Synthesis, structure and magnetic properties of a V^IV^O^2+^ complex with a new ligand derived from glycine. ; loop_ _publ_author_name _publ_author_address 'Ceccato, Augusto S.' ; Depto. Qu\'imica - UFSC 88040-900 - Florian\'opolis, SC Brazil ; 'Neves, Ademir' ; Depto. Qu\'imica - UFSC 88040-900 - Florian\'opolis, SC Brazil ; 'de Brito, Marcos A.' ; Depto. Qu\'imica - UFSC 88040-900 - Florian\'opolis, SC Brazil ; 'Drechsel, Sueli M.' ; Depto. Qu\'imica - UFPR 81531-970 - Curitiba, PR Brazil ; 'Mangrich, Antonio S.' ; Depto. Qu\'imica - UFPR 81531-970 - Curitiba, PR Brazil ; 'Werner, Ru\"diger' ; Institut f\=FCr Physikalische Chemie, Technische Hochschule, D-6100 Darmstadt Germany ; 'Haase, Wolfgang' ; Institut f\"ur Physikalische Chemie, Technische Hochschule, D-6100 Darmstadt Germany ; 'Bortoluzzi, Adailton J.' ; Depto. Qu\'imica - UFSM 97119-900 - Santa Maria, RS Brazil ; _publ_section_references ; Enraf-Nonius (1994). CAD-4 EXPRESS. Version 5.1/1.2. Enraf-Nonius, Delft, The Netherlands. Sheldrick, G. M. (1997a). SHELXS97. Program for the Solution of Crystal Structures. Univ. of G\"ottingen, Germany. Sheldrick, G. M. (1997b). SHELXL97. Program for the Refinement of Crystal Structures. Univ. of G\"ottingen, Germany. Spek, A. L. (1990). Acta Cryst. A36, C--34. Spek, A. L. (1996). HELENA. Program for Reduction of CAD-4 Data. University of Utrecht. The Netherlands. Zsolnai, L., Pritzkow, H. & Hutter, G. (1996). ZORTEP. University of Heidelberg, Germany. ; _chemical_name_systematic ; Triethylammonium-bis{[N,N-bis(2-oxyphenyl)glycinate] oxovanadium(IV)} dichloromethane solvate ; _chemical_name_common ? _chemical_formula_sum 'C48 H68 Cl8 N4 O10 V2' _chemical_formula_moiety ; C32 H28 N2 O12 V2, 2(C6 H16 N), 4(C H2 Cl2) ; _chemical_formula_weight 1246.54 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' 'Cl' 'Cl' 0.1484 0.1585 '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 Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.638(2) _cell_length_b 11.380(2) _cell_length_c 13.512(2) _cell_angle_alpha 98.11(3) _cell_angle_beta 102.00(3) _cell_angle_gamma 110.17(3) _cell_volume 1461.0(4) _cell_formula_units_Z 1 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7.57 _cell_measurement_theta_max 13.85 _exptl_crystal_description prism _exptl_crystal_colour violet _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 646 _exptl_absorpt_coefficient_mu 0.741 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details 'PLATON (Spek, 1990)' _exptl_absorpt_correction_T_min 0.9143 _exptl_absorpt_correction_T_max 0.9999 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD-4 diffractometer' _diffrn_measurement_method \w--2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time '60 min' _diffrn_standards_decay_% 4.1 _diffrn_reflns_number 5432 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0187 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5133 _reflns_number_gt 4570 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CAD4-EXPRESS (Enraf-Nonius, 1994)' _computing_cell_refinement ; SET4 in CAD4 EXPRESS (Enraf-Nonius, 1994) ; _computing_data_reduction 'HELENA (Spek, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997b)' _computing_molecular_graphics ; ZORTEP (Zsolnai et al., 1996) ; _computing_publication_material ; SHELXL97. All calculations were performed on a PC/Pentim II computer running LINUX. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=3D1/[\s^2^(Fo^2^)+(0.0681P)^2^+0.8873P] where P=3D(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 SHELXL _refine_ls_extinction_coef 0.0031(14) _refine_ls_extinction_expression 'Fc^*^=3DkFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5133 _refine_ls_number_parameters 348 _refine_ls_number_restraints 43 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1149 _refine_ls_wR_factor_gt 0.1105 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.101 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group V1 V 0.54336(4) 0.94422(3) 0.59474(3) 0.02129(14) Uani 1 d . . . O1 O 0.69705(16) 1.05088(15) 0.65300(12) 0.0294(4) Uani 1 d . . . O2 O 0.36293(16) 0.77177(14) 0.50926(12) 0.0273(3) Uani 1 d . . . O3 O 0.26460(17) 0.55819(15) 0.48578(14) 0.0369(4) Uani 1 d . . . O10 O 0.47505(17) 0.90904(15) 0.71489(12) 0.0296(4) Uani 1 d . . . O20 O 0.56124(15) 0.94190(14) 0.44359(11) 0.0239(3) Uani 1 d . . . N1 N 0.61691(18) 0.79208(17) 0.60899(14) 0.0226(4) Uani 1 d . . . C1 C 0.4999(2) 0.6652(2) 0.58679(17) 0.0248(5) Uani 1 d . . . H1A H 0.4864 0.6442 0.6519 0.030 Uiso 1 calc R . . H1B H 0.5239 0.5995 0.5507 0.030 Uiso 1 calc R . . C2 C 0.3655(2) 0.6641(2) 0.52113(17) 0.0256(5) Uani 1 d . . . C10 C 0.7093(2) 0.8193(2) 0.71599(17) 0.0279(5) Uani 1 d . . . H10A H 0.7865 0.9013 0.7290 0.033 Uiso 1 calc R . . H10B H 0.7478 0.7536 0.7194 0.033 Uiso 1 calc R . . C11 C 0.6374(2) 0.8234(2) 0.80036(17) 0.0278(5) Uani 1 d . . . C12 C 0.5293(2) 0.8705(2) 0.79618(17) 0.0261(5) Uani 1 d . . . C13 C 0.4757(3) 0.8738(2) 0.88261(19) 0.0337(5) Uani 1 d . . . H13A H 0.4051 0.9045 0.8818 0.040 Uiso 1 calc R . . C14 C 0.5245(3) 0.8329(3) 0.9690(2) 0.0423(6) Uani 1 d . . . H14A H 0.4875 0.8376 1.0254 0.051 Uiso 1 calc R . . C15 C 0.6273(3) 0.7855(3) 0.9720(2) 0.0489(7) Uani 1 d . . . H15A H 0.6598 0.7572 1.0296 0.059 Uiso 1 calc R . . C16 C 0.6818(3) 0.7804(3) 0.8880(2) 0.0402(6) Uani 1 d . . . H16A H 0.7506 0.7472 0.8898 0.048 Uiso 1 calc R . . C20 C 0.7040(2) 0.7936(2) 0.53476(18) 0.0265(5) Uani 1 d . . . H20A H 0.7492 0.7339 0.5461 0.032 Uiso 1 calc R . . H20B H 0.7764 0.8790 0.5499 0.032 Uiso 1 calc R . . C21 C 0.6229(2) 0.7585(2) 0.42234(17) 0.0252(5) Uani 1 d . . . C22 C 0.5570(2) 0.8355(2) 0.38017(17) 0.0242(4) Uani 1 d . . . C23 C 0.4905(2) 0.8025(2) 0.27429(18) 0.0287(5) Uani 1 d . . . H23A H 0.4478 0.8535 0.2458 0.034 Uiso 1 calc R . . C24 C 0.4875(3) 0.6938(2) 0.21088(19) 0.0333(5) Uani 1 d . . . H24A H 0.4430 0.6728 0.1401 0.040 Uiso 1 calc R . . C25 C 0.5501(3) 0.6162(2) 0.2521(2) 0.0354(6) Uani 1 d . . . H25A H 0.5472 0.5430 0.2096 0.042 Uiso 1 calc R . . C26 C 0.6168(2) 0.6491(2) 0.35701(19) 0.0307(5) Uani 1 d . . . H26A H 0.6587 0.5971 0.3848 0.037 Uiso 1 calc R . . N1N N 0.0612(2) 0.5897(2) 0.34320(17) 0.0317(4) Uani 1 d . . . H1NA H 0.121(3) 0.590(3) 0.394(2) 0.043(8) Uiso 1 d . . . C11N C -0.0648(3) 0.4706(3) 0.3314(2) 0.0452(7) Uani 1 d . . . H11A H -0.0930 0.4758 0.3951 0.054 Uiso 1 calc R . . H11B H -0.0393 0.3966 0.3222 0.054 Uiso 1 calc R . . C12N C -0.1874(3) 0.4491(4) 0.2417(3) 0.0741(12) Uani 1 d . . . H12B H -0.2635 0.3717 0.2392 0.111 Uiso 1 calc R . . H12C H -0.1615 0.4413 0.1778 0.111 Uiso 1 calc R . . H12D H -0.2153 0.5208 0.2508 0.111 Uiso 1 calc R . . C21N C 0.1170(3) 0.5926(3) 0.2501(2) 0.0446(6) Uani 1 d . . . H21A H 0.2000 0.6705 0.2650 0.054 Uiso 1 calc R . . H21B H 0.0483 0.5958 0.1920 0.054 Uiso 1 calc R . . C22N C 0.1526(3) 0.4783(3) 0.2193(3) 0.0547(8) Uani 1 d . . . H22B H 0.1881 0.4856 0.1597 0.082 Uiso 1 calc R . . H22C H 0.0705 0.4009 0.2026 0.082 Uiso 1 calc R . . H22D H 0.2221 0.4755 0.2760 0.082 Uiso 1 calc R . . C31N C 0.0397(3) 0.7115(2) 0.3744(2) 0.0409(6) Uani 1 d . . . H31A H 0.1196 0.7840 0.3719 0.049 Uiso 1 calc R . . H31B H -0.0417 0.7096 0.3248 0.049 Uiso 1 calc R . . C32N C 0.0204(3) 0.7304(3) 0.4812(2) 0.0493(7) Uani 1 d . . . H32A H 0.0071 0.8094 0.4976 0.074 Uiso 1 calc R . . H32B H 0.1014 0.7341 0.5308 0.074 Uiso 1 calc R . . H32C H -0.0599 0.6598 0.4838 0.074 Uiso 1 calc R . . C41 C 0.1983(3) 0.9884(3) 0.7413(3) 0.0532(8) Uani 1 d . . . H41A H 0.2666 1.0586 0.7974 0.064 Uiso 1 calc R . . H41B H 0.2480 0.9533 0.7009 0.064 Uiso 1 calc R . . Cl42 Cl 0.09799(9) 0.86788(9) 0.79403(8) 0.0684(3) Uani 1 d . . . Cl43 Cl 0.09310(9) 1.04762(8) 0.66132(8) 0.0633(3) Uani 1 d . . . C51 C 0.1641(4) 0.8592(4) 1.0855(3) 0.0740(11) Uani 1 d D . . Cl52 Cl 0.1595(7) 0.7110(4) 1.0216(4) 0.0666(14) Uani 0.50 d PDU . . Cl53 Cl 0.0070(4) 0.8635(4) 1.0736(4) 0.0978(13) Uani 0.50 d PDU . . Cl52' Cl 0.1798(7) 0.7272(6) 1.0282(6) 0.095(2) Uani 0.50 d PDU . . Cl53' Cl -0.0210(6) 0.8068(7) 1.0927(4) 0.154(3) Uani 0.50 d PDU . . 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 0.0229(2) 0.0150(2) 0.0272(2) 0.00793(14) 0.00753(15) 0.00734(15) O1 0.0289(8) 0.0209(8) 0.0349(9) 0.0075(6) 0.0061(7) 0.0067(7) O2 0.0251(8) 0.0202(8) 0.0364(9) 0.0117(6) 0.0060(7) 0.0080(6) O3 0.0299(9) 0.0197(8) 0.0505(10) 0.0101(7) 0.0013(8) 0.0021(7) O10 0.0345(9) 0.0318(9) 0.0338(9) 0.0179(7) 0.0148(7) 0.0192(7) O20 0.0286(8) 0.0180(7) 0.0288(8) 0.0077(6) 0.0102(6) 0.0111(6) N1 0.0219(9) 0.0175(9) 0.0286(9) 0.0075(7) 0.0064(7) 0.0075(7) C1 0.0280(11) 0.0157(10) 0.0303(11) 0.0076(8) 0.0079(9) 0.0072(9) C2 0.0259(11) 0.0228(11) 0.0284(11) 0.0082(9) 0.0097(9) 0.0076(9) C10 0.0247(11) 0.0266(11) 0.0326(12) 0.0084(9) 0.0031(9) 0.0125(9) C11 0.0301(12) 0.0223(11) 0.0284(11) 0.0052(9) 0.0040(9) 0.0095(9) C12 0.0287(11) 0.0175(10) 0.0296(11) 0.0072(9) 0.0065(9) 0.0061(9) C13 0.0360(13) 0.0333(13) 0.0336(12) 0.0095(10) 0.0114(10) 0.0137(11) C14 0.0516(16) 0.0491(16) 0.0312(13) 0.0146(12) 0.0155(12) 0.0210(13) C15 0.0643(19) 0.0602(19) 0.0324(14) 0.0202(13) 0.0106(13) 0.0341(16) C16 0.0452(15) 0.0476(16) 0.0328(13) 0.0116(11) 0.0046(11) 0.0268(13) C20 0.0241(11) 0.0249(11) 0.0358(12) 0.0112(9) 0.0110(9) 0.0126(9) C21 0.0263(11) 0.0221(11) 0.0323(12) 0.0105(9) 0.0140(9) 0.0103(9) C22 0.0254(11) 0.0183(10) 0.0317(11) 0.0088(9) 0.0130(9) 0.0075(8) C23 0.0348(12) 0.0250(11) 0.0316(12) 0.0117(9) 0.0122(10) 0.0142(10) C24 0.0405(13) 0.0296(12) 0.0306(12) 0.0065(10) 0.0115(10) 0.0135(11) C25 0.0453(14) 0.0254(12) 0.0393(13) 0.0055(10) 0.0173(11) 0.0158(11) C26 0.0354(13) 0.0226(11) 0.0419(13) 0.0117(10) 0.0169(11) 0.0154(10) N1N 0.0264(10) 0.0283(11) 0.0392(11) 0.0120(9) 0.0077(9) 0.0082(9) C11N 0.0409(15) 0.0269(13) 0.0600(18) 0.0048(12) 0.0229(13) 0.0007(11) C12N 0.0331(16) 0.072(2) 0.086(3) -0.026(2) 0.0063(16) 0.0060(16) C21N 0.0414(15) 0.0456(16) 0.0527(16) 0.0207(13) 0.0225(13) 0.0145(13) C22N 0.0520(18) 0.0505(18) 0.064(2) 0.0096(15) 0.0266(15) 0.0184(15) C31N 0.0400(14) 0.0275(13) 0.0566(16) 0.0153(12) 0.0120(12) 0.0134(11) C32N 0.0480(16) 0.0413(16) 0.0634(19) 0.0088(14) 0.0193(14) 0.0219(13) C41 0.0388(15) 0.0428(17) 0.074(2) 0.0211(15) 0.0125(14) 0.0103(13) Cl42 0.0610(5) 0.0599(5) 0.0973(7) 0.0457(5) 0.0304(5) 0.0234(4) Cl43 0.0601(5) 0.0529(5) 0.0900(6) 0.0360(4) 0.0233(4) 0.0284(4) C51 0.079(3) 0.059(2) 0.060(2) -0.0008(17) -0.0029(19) 0.017(2) Cl52 0.104(3) 0.0543(13) 0.0465(18) 0.0050(11) 0.0253(18) 0.0360(14) Cl53 0.0706(15) 0.118(3) 0.098(3) -0.008(2) 0.0028(16) 0.0529(17) Cl52' 0.073(2) 0.167(5) 0.067(3) 0.041(3) 0.0256(17) 0.062(3) Cl53' 0.171(5) 0.290(8) 0.092(2) 0.063(4) 0.043(3) 0.187(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 V1 O1 1.6102(18) . ? V1 O10 1.9487(16) . ? V1 O20 2.0323(15) 2_676 ? V1 O20 2.0876(15) . ? V1 N1 2.1476(18) . ? V1 O2 2.1703(19) . ? O2 C2 1.267(3) . ? O3 C2 1.251(3) . ? O10 C12 1.334(3) . ? O20 C22 1.362(3) . ? O20 V1 2.0323(15) 2_676 ? N1 C1 1.486(3) . ? N1 C10 1.492(3) . ? N1 C20 1.498(3) . ? C1 C2 1.513(3) . ? C10 C11 1.504(3) . ? C11 C16 1.399(3) . ? C11 C12 1.421(3) . ? C12 C13 1.404(3) . ? C13 C14 1.385(4) . ? C14 C15 1.373(4) . ? C15 C16 1.379(4) . ? C20 C21 1.502(3) . ? C21 C26 1.394(3) . ? C21 C22 1.409(3) . ? C22 C23 1.390(3) . ? C23 C24 1.388(3) . ? C24 C25 1.387(4) . ? C25 C26 1.379(4) . ? N1N H1NA 0.84(3) . ? N1N C21N 1.498(3) . ? N1N C31N 1.498(3) . ? N1N C11N 1.502(3) . ? C11N C12N 1.506(5) . ? C21N C22N 1.504(4) . ? C31N C32N 1.497(4) . ? C41 Cl43 1.759(3) . ? C41 Cl42 1.764(3) . ? C51 Cl53 1.664(6) . ? C51 Cl52' 1.669(7) . ? C51 Cl52 1.763(5) . ? C51 Cl53' 1.879(7) . ? Cl53 Cl53' 0.719(8) . ? 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 O10 99.77(8) . . ? O1 V1 O20 100.85(7) . 2_676 ? O10 V1 O20 95.92(7) . 2_676 ? O1 V1 O20 96.45(8) . . ? O10 V1 O20 163.77(7) . . ? O20 V1 O20 81.38(7) 2_676 . ? O1 V1 N1 90.94(8) . . ? O10 V1 N1 86.11(7) . . ? O20 V1 N1 167.48(7) 2_676 . ? O20 V1 N1 93.22(7) . . ? O1 V1 O2 166.44(7) . . ? O10 V1 O2 84.49(7) . . ? O20 V1 O2 91.43(6) 2_676 . ? O20 V1 O2 79.60(7) . . ? N1 V1 O2 76.44(7) . . ? C2 O2 V1 117.98(14) . . ? C12 O10 V1 129.19(14) . . ? C22 O20 V1 126.69(14) . 2_676 ? C22 O20 V1 122.20(13) . . ? V1 O20 V1 98.62(7) 2_676 . ? C1 N1 C10 109.47(17) . . ? C1 N1 C20 111.43(17) . . ? C10 N1 C20 107.48(17) . . ? C1 N1 V1 111.72(13) . . ? C10 N1 V1 109.80(13) . . ? C20 N1 V1 106.82(13) . . ? N1 C1 C2 112.10(17) . . ? O3 C2 O2 125.1(2) . . ? O3 C2 C1 117.81(19) . . ? O2 C2 C1 117.01(19) . . ? N1 C10 C11 114.03(18) . . ? C16 C11 C12 118.8(2) . . ? C16 C11 C10 117.7(2) . . ? C12 C11 C10 123.5(2) . . ? O10 C12 C13 118.7(2) . . ? O10 C12 C11 124.0(2) . . ? C13 C12 C11 117.3(2) . . ? C14 C13 C12 122.2(2) . . ? C15 C14 C13 120.3(2) . . ? C14 C15 C16 119.0(2) . . ? C15 C16 C11 122.4(2) . . ? N1 C20 C21 113.85(18) . . ? C26 C21 C22 119.0(2) . . ? C26 C21 C20 119.2(2) . . ? C22 C21 C20 121.8(2) . . ? O20 C22 C23 121.2(2) . . ? O20 C22 C21 119.4(2) . . ? C23 C22 C21 119.3(2) . . ? C24 C23 C22 120.4(2) . . ? C25 C24 C23 120.6(2) . . ? C26 C25 C24 119.1(2) . . ? C25 C26 C21 121.5(2) . . ? H1NA N1N C21N 109(2) . . ? H1NA N1N C31N 105(2) . . ? C21N N1N C31N 110.0(2) . . ? H1NA N1N C11N 105(2) . . ? C21N N1N C11N 114.1(2) . . ? C31N N1N C11N 113.1(2) . . ? N1N C11N C12N 114.3(3) . . ? N1N C21N C22N 113.2(2) . . ? C32N C31N N1N 112.6(2) . . ? Cl43 C41 Cl42 111.41(17) . . ? Cl53 C51 Cl52 113.4(3) . . ? Cl53 C51 Cl52' 120.0(4) . . ? Cl52' C51 Cl52 6.6(4) . . ? Cl53 C51 Cl53' 22.4(2) . . ? Cl52' C51 Cl53' 105.9(4) . . ? Cl52 C51 Cl53' 99.4(4) . . ? Cl53' Cl53 C51 95.9(7) . . ? Cl53 Cl53' C51 61.8(7) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N1N H1NA O2 0.84(3) 2.66(3) 3.277(3) 131(3) . . N1N H1NA O3 0.84(3) 1.92(3) 2.742(3) 165(3) . . _diffrn_measured_fraction_t=D3eta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.515 _refine_diff_density_min -0.734 _refine_diff_density_rms 0.064