# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Colin Abernethy' ; Department of Chemistry Keene State College Keene, NH 03435-2001 USA ; ; ? ; 'Michael Findlater' ; Department of Chemistry Keene State College Keene, NH 03435-2001 USA ; ; ? ; 'Jerry P. Jasinski' ; Department of Chemistry The University of North Carolina at Chapel Hill Chapel Hill, NC 27599-3290 USA ; ; ? ; 'Carl E Johnson' ; Department of Chemistry Keene State College Keene, NH 03435-2001 USA ; ; ? ; 'Everett A. Kysor' ; Department of Chemistry Keene State College Keene, NH 03435-2001 USA ; ; ? ; 'Andrew S Metell' ; Department of Chemistry Keene State College Keene, NH 03435-2001 USA ; ; ? ; 'Jonathan W Queen' ; Department of Chemistry Keene State College Keene, NH 03435-2001 USA ; ; Correspondence e-mail: cabernethy@keene.edu ; _publ_contact_author_name 'Colin Abernethy' _publ_contact_author_email CABERNETHY@KEENE.EDU _publ_section_title ; The Synthesis and Characterization of [IMesH]+[(?3-C5H5)V(N)Cl2]-: An Example of Cyclopentadienyl Ring-slippage Induced by a Strongly ?-basic Coligand ; _publ_contact_letter ; Please consider this CIF submission for publication in Dalton Transactions ; _publ_contact_author_address ; Department of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001 USA. ; _publ_contact_author_fax '603 358-2897' _publ_contact_author_phone '603 358-2560' _publ_requested_category EO _publ_requested_coeditor_name unknown _publ_requested_journal 'Dalton Transactions' # Attachment '[IMes]+[CpVCl3]-_Dalton.cif' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 752793' #TrackingRef '[IMes]+[CpVCl3]-_Dalton.cif' _audit_update_record ; 2009-10-29 # Formatted by publCIF ; _audit_creation_method ; manual editing of the .cif file created by SHELXTL Ver. 6.10 ; _publ_section_references ; Allen, F. H. (2002). Acta Cryst. B58, 380--388. Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1358--1367. Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999). J. Appl. Cryst. 32, 115--119. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, 276 Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. Sluis, P. v.d. & Spek, A. L. (1990). SQUEEZE. Acta Cryst. A46, 194--201. Spek, A. L. (1998). PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H25 N2, C5 H5 Cl3 V' _chemical_formula_sum 'C26 H30 Cl3 N2 V' _chemical_formula_weight 527.81 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' 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 monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.543(6) _cell_length_b 14.710(3) _cell_length_c 14.792(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.19(3) _cell_angle_gamma 90.00 _cell_volume 6411(2) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.094 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2592 _exptl_absorpt_coefficient_mu 0.584 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; A disordered molecule of what appeared to be toluene was removed using the SQUEEZE command in PLATON ; _diffrn_ambient_temperature 153(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 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12353 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.0783 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 27.49 _reflns_number_total 7233 _reflns_number_gt 4594 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1039P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7233 _refine_ls_number_parameters 295 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1041 _refine_ls_R_factor_gt 0.0646 _refine_ls_wR_factor_ref 0.1834 _refine_ls_wR_factor_gt 0.1669 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.014 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3478(4) 0.2219(3) -0.0328(4) 0.109(3) Uani 1 1 d . . . H1 H 0.3477 0.2768 -0.0639 0.131 Uiso 1 1 calc R . . C2 C 0.31072(19) 0.1638(4) -0.0256(3) 0.0677(14) Uani 1 1 d . . . H2 H 0.2811 0.1730 -0.0499 0.081 Uiso 1 1 calc R . . C3 C 0.32682(16) 0.0909(2) 0.0246(3) 0.0520(11) Uani 1 1 d . . . H3 H 0.3098 0.0406 0.0395 0.062 Uiso 1 1 calc R . . C4 C 0.37138(17) 0.1039(4) 0.0489(3) 0.0659(13) Uani 1 1 d . . . H4 H 0.3899 0.0643 0.0840 0.079 Uiso 1 1 calc R . . C5 C 0.3845(2) 0.1826(5) 0.0145(5) 0.097(3) Uani 1 1 d . . . H5 H 0.4136 0.2068 0.0214 0.116 Uiso 1 1 calc R . . C6 C 0.19133(9) -0.0086(2) 0.0917(2) 0.0260(6) Uani 1 1 d . . . H6 H 0.2021 0.0425 0.0632 0.031 Uiso 1 1 calc R . . C7 C 0.18740(11) -0.1443(2) 0.1531(2) 0.0312(7) Uani 1 1 d . . . H7 H 0.1955 -0.2022 0.1738 0.037 Uiso 1 1 calc R . . C8 C 0.14676(11) -0.1042(2) 0.1589(2) 0.0320(7) Uani 1 1 d . . . H8 H 0.1216 -0.1290 0.1840 0.038 Uiso 1 1 calc R . . C9 C 0.26068(9) -0.10465(18) 0.0882(2) 0.0247(6) Uani 1 1 d . . . C10 C 0.26744(10) -0.12433(18) -0.0016(2) 0.0262(7) Uani 1 1 d . . . C11 C 0.31152(11) -0.1455(2) -0.0218(3) 0.0344(8) Uani 1 1 d . . . H11 H 0.3173 -0.1573 -0.0816 0.041 Uiso 1 1 calc R . . C12 C 0.34684(11) -0.1495(2) 0.0443(3) 0.0401(9) Uani 1 1 d . . . C13 C 0.33811(11) -0.1304(2) 0.1331(3) 0.0423(9) Uani 1 1 d . . . H13 H 0.3617 -0.1345 0.1781 0.051 Uiso 1 1 calc R . . C14 C 0.29481(11) -0.1051(2) 0.1577(2) 0.0320(7) Uani 1 1 d . . . C15 C 0.22932(11) -0.1230(2) -0.0749(2) 0.0350(7) Uani 1 1 d . . . H15A H 0.2194 -0.0615 -0.0854 0.053 Uiso 1 1 calc R . . H15B H 0.2045 -0.1588 -0.0562 0.053 Uiso 1 1 calc R . . H15C H 0.2397 -0.1478 -0.1297 0.053 Uiso 1 1 calc R . . C16 C 0.39400(13) -0.1738(3) 0.0199(4) 0.0725(15) Uani 1 1 d . . . H16A H 0.4021 -0.1366 -0.0298 0.109 Uiso 1 1 calc R . . H16B H 0.3948 -0.2367 0.0026 0.109 Uiso 1 1 calc R . . H16C H 0.4152 -0.1637 0.0713 0.109 Uiso 1 1 calc R . . C17 C 0.28659(14) -0.0779(3) 0.2534(3) 0.0492(10) Uani 1 1 d . . . H17A H 0.2753 -0.0167 0.2537 0.074 Uiso 1 1 calc R . . H17B H 0.3145 -0.0816 0.2906 0.074 Uiso 1 1 calc R . . H17C H 0.2647 -0.1182 0.2767 0.074 Uiso 1 1 calc R . . C18 C 0.11283(9) 0.04610(19) 0.1128(2) 0.0247(6) Uani 1 1 d . . . C19 C 0.08120(10) 0.0403(2) 0.0388(2) 0.0314(7) Uani 1 1 d . . . C20 C 0.04485(10) 0.1003(2) 0.0361(3) 0.0388(8) Uani 1 1 d . . . H20 H 0.0230 0.0976 -0.0124 0.047 Uiso 1 1 calc R . . C21 C 0.04030(11) 0.1641(3) 0.1037(3) 0.0406(8) Uani 1 1 d . . . C22 C 0.07311(11) 0.1675(2) 0.1761(2) 0.0370(8) Uani 1 1 d . . . H22 H 0.0701 0.2104 0.2215 0.044 Uiso 1 1 calc R . . C23 C 0.11021(10) 0.1092(2) 0.1829(2) 0.0282(7) Uani 1 1 d . . . C24 C 0.08573(12) -0.0289(3) -0.0356(3) 0.0416(8) Uani 1 1 d . . . H24A H 0.1102 -0.0117 -0.0713 0.062 Uiso 1 1 calc R . . H24B H 0.0580 -0.0314 -0.0735 0.062 Uiso 1 1 calc R . . H24C H 0.0919 -0.0876 -0.0091 0.062 Uiso 1 1 calc R . . C25 C 0.00075(14) 0.2301(3) 0.0986(4) 0.0669(13) Uani 1 1 d . . . H25A H -0.0213 0.2105 0.1390 0.100 Uiso 1 1 calc R . . H25B H -0.0129 0.2318 0.0377 0.100 Uiso 1 1 calc R . . H25C H 0.0115 0.2896 0.1159 0.100 Uiso 1 1 calc R . . C26 C 0.14574(11) 0.1147(2) 0.2603(2) 0.0375(8) Uani 1 1 d . . . H26A H 0.1510 0.0553 0.2857 0.056 Uiso 1 1 calc R . . H26B H 0.1356 0.1548 0.3059 0.056 Uiso 1 1 calc R . . H26C H 0.1734 0.1377 0.2389 0.056 Uiso 1 1 calc R . . N1 N 0.21459(8) -0.08465(16) 0.11147(17) 0.0244(5) Uani 1 1 d . . . N2 N 0.14969(8) -0.01902(16) 0.12026(18) 0.0257(6) Uani 1 1 d . . . Cl1 Cl 0.26331(3) 0.18007(6) 0.17881(6) 0.0423(2) Uani 1 1 d . . . Cl2 Cl 0.32085(3) 0.37322(5) 0.10830(6) 0.0400(2) Uani 1 1 d . . . Cl3 Cl 0.37732(4) 0.19581(7) 0.24631(7) 0.0544(3) Uani 1 1 d . . . V1 V 0.331403(19) 0.21635(3) 0.11401(4) 0.03002(18) 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 0.254(10) 0.026(2) 0.061(4) 0.000(2) 0.099(5) -0.006(4) C2 0.090(3) 0.081(4) 0.031(2) -0.024(2) -0.006(2) 0.030(3) C3 0.080(3) 0.0314(19) 0.049(2) -0.0162(18) 0.032(2) -0.0152(18) C4 0.062(3) 0.079(3) 0.057(3) -0.026(3) 0.009(2) 0.018(2) C5 0.088(4) 0.097(4) 0.114(6) -0.065(4) 0.074(4) -0.048(4) C6 0.0233(14) 0.0275(15) 0.0272(17) 0.0053(13) 0.0009(12) 0.0005(11) C7 0.0410(18) 0.0221(15) 0.0310(18) 0.0057(13) 0.0057(14) 0.0012(12) C8 0.0352(17) 0.0304(17) 0.0313(19) 0.0059(14) 0.0091(14) -0.0043(13) C9 0.0256(15) 0.0195(14) 0.0291(17) 0.0070(12) 0.0018(13) 0.0045(11) C10 0.0326(16) 0.0157(14) 0.0299(18) 0.0003(12) 0.0002(13) 0.0015(11) C11 0.0401(18) 0.0217(15) 0.042(2) -0.0029(14) 0.0088(16) 0.0024(13) C12 0.0286(17) 0.0305(17) 0.061(3) -0.0018(16) 0.0050(17) 0.0077(13) C13 0.0289(17) 0.0343(19) 0.061(3) 0.0079(17) -0.0138(17) 0.0026(13) C14 0.0344(17) 0.0291(16) 0.0316(19) 0.0089(14) -0.0031(14) -0.0028(13) C15 0.0395(18) 0.0360(18) 0.0290(19) -0.0012(15) -0.0025(15) 0.0034(14) C16 0.031(2) 0.076(3) 0.110(4) -0.019(3) 0.007(2) 0.0186(19) C17 0.053(2) 0.064(2) 0.029(2) 0.0072(18) -0.0090(17) -0.0055(18) C18 0.0188(13) 0.0286(15) 0.0272(17) 0.0048(13) 0.0046(12) -0.0008(11) C19 0.0271(15) 0.0385(17) 0.0289(18) 0.0039(14) 0.0038(13) -0.0052(13) C20 0.0226(16) 0.055(2) 0.038(2) 0.0073(17) -0.0043(14) 0.0038(14) C21 0.0260(16) 0.051(2) 0.045(2) 0.0056(18) 0.0045(15) 0.0094(14) C22 0.0328(17) 0.0418(19) 0.038(2) -0.0035(16) 0.0126(15) 0.0034(14) C23 0.0287(15) 0.0352(16) 0.0213(16) 0.0052(13) 0.0048(13) -0.0031(12) C24 0.0362(19) 0.053(2) 0.035(2) -0.0073(17) -0.0021(16) -0.0048(15) C25 0.037(2) 0.080(3) 0.082(4) -0.005(3) -0.002(2) 0.025(2) C26 0.0381(18) 0.045(2) 0.0287(19) 0.0007(16) 0.0016(15) 0.0008(15) N1 0.0257(12) 0.0243(13) 0.0233(14) 0.0056(10) 0.0017(10) 0.0011(9) N2 0.0248(13) 0.0255(13) 0.0268(15) 0.0043(11) 0.0023(10) -0.0009(9) Cl1 0.0473(5) 0.0426(5) 0.0387(5) -0.0005(4) 0.0161(4) -0.0125(4) Cl2 0.0624(6) 0.0241(4) 0.0347(5) 0.0011(3) 0.0111(4) -0.0012(3) Cl3 0.0601(6) 0.0539(6) 0.0471(6) -0.0126(5) -0.0096(5) 0.0200(4) V1 0.0405(3) 0.0234(3) 0.0273(3) -0.0032(2) 0.0094(2) -0.0053(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C5 1.374(10) . ? C1 C2 1.399(9) . ? C1 V1 2.261(5) . ? C1 H1 0.9300 . ? C2 C3 1.370(6) . ? C2 V1 2.247(4) . ? C2 H2 0.9300 . ? C3 C4 1.352(6) . ? C3 V1 2.269(4) . ? C3 H3 0.9300 . ? C4 C5 1.334(9) . ? C4 V1 2.286(4) . ? C4 H4 0.9300 . ? C5 V1 2.283(5) . ? C5 H5 0.9300 . ? C6 N1 1.334(4) . ? C6 N2 1.338(4) . ? C6 H6 0.9300 . ? C7 C8 1.346(4) . ? C7 N1 1.366(4) . ? C7 H7 0.9300 . ? C8 N2 1.382(4) . ? C8 H8 0.9300 . ? C9 C14 1.386(4) . ? C9 C10 1.389(4) . ? C9 N1 1.459(4) . ? C10 C11 1.392(4) . ? C10 C15 1.504(5) . ? C11 C12 1.377(5) . ? C11 H11 0.9300 . ? C12 C13 1.386(6) . ? C12 C16 1.508(5) . ? C13 C14 1.405(5) . ? C13 H13 0.9300 . ? C14 C17 1.508(5) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.389(5) . ? C18 C23 1.397(4) . ? C18 N2 1.448(4) . ? C19 C20 1.389(5) . ? C19 C24 1.512(5) . ? C20 C21 1.384(5) . ? C20 H20 0.9300 . ? C21 C22 1.392(5) . ? C21 C25 1.517(5) . ? C22 C23 1.390(4) . ? C22 H22 0.9300 . ? C23 C26 1.498(5) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? Cl1 V1 2.3523(11) . ? Cl2 V1 2.3292(10) . ? Cl3 V1 2.3180(14) . ? 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 C5 C1 C2 107.3(4) . . ? C5 C1 V1 73.3(3) . . ? C2 C1 V1 71.4(3) . . ? C5 C1 H1 126.4 . . ? C2 C1 H1 126.4 . . ? V1 C1 H1 120.8 . . ? C3 C2 C1 106.0(5) . . ? C3 C2 V1 73.2(2) . . ? C1 C2 V1 72.5(3) . . ? C3 C2 H2 127.0 . . ? C1 C2 H2 127.0 . . ? V1 C2 H2 119.4 . . ? C4 C3 C2 109.1(4) . . ? C4 C3 V1 73.4(2) . . ? C2 C3 V1 71.5(2) . . ? C4 C3 H3 125.5 . . ? C2 C3 H3 125.5 . . ? V1 C3 H3 121.3 . . ? C5 C4 C3 109.0(5) . . ? C5 C4 V1 72.9(3) . . ? C3 C4 V1 72.0(2) . . ? C5 C4 H4 125.5 . . ? C3 C4 H4 125.5 . . ? V1 C4 H4 121.2 . . ? C4 C5 C1 108.6(5) . . ? C4 C5 V1 73.2(3) . . ? C1 C5 V1 71.5(3) . . ? C4 C5 H5 125.7 . . ? C1 C5 H5 125.7 . . ? V1 C5 H5 121.3 . . ? N1 C6 N2 107.8(2) . . ? N1 C6 H6 126.1 . . ? N2 C6 H6 126.1 . . ? C8 C7 N1 107.7(3) . . ? C8 C7 H7 126.2 . . ? N1 C7 H7 126.2 . . ? C7 C8 N2 106.7(3) . . ? C7 C8 H8 126.6 . . ? N2 C8 H8 126.6 . . ? C14 C9 C10 124.1(3) . . ? C14 C9 N1 117.8(3) . . ? C10 C9 N1 118.0(3) . . ? C9 C10 C11 117.0(3) . . ? C9 C10 C15 122.3(3) . . ? C11 C10 C15 120.8(3) . . ? C12 C11 C10 122.0(3) . . ? C12 C11 H11 119.0 . . ? C10 C11 H11 119.0 . . ? C11 C12 C13 118.7(3) . . ? C11 C12 C16 120.4(4) . . ? C13 C12 C16 120.9(4) . . ? C12 C13 C14 122.3(3) . . ? C12 C13 H13 118.8 . . ? C14 C13 H13 118.8 . . ? C9 C14 C13 115.9(3) . . ? C9 C14 C17 122.4(3) . . ? C13 C14 C17 121.7(3) . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C12 C16 H16A 109.5 . . ? C12 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C12 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C23 123.7(3) . . ? C19 C18 N2 118.6(3) . . ? C23 C18 N2 117.7(3) . . ? C18 C19 C20 117.3(3) . . ? C18 C19 C24 121.6(3) . . ? C20 C19 C24 121.1(3) . . ? C21 C20 C19 121.7(3) . . ? C21 C20 H20 119.2 . . ? C19 C20 H20 119.2 . . ? C20 C21 C22 118.8(3) . . ? C20 C21 C25 120.9(4) . . ? C22 C21 C25 120.3(4) . . ? C23 C22 C21 122.2(3) . . ? C23 C22 H22 118.9 . . ? C21 C22 H22 118.9 . . ? C22 C23 C18 116.3(3) . . ? C22 C23 C26 121.7(3) . . ? C18 C23 C26 122.0(3) . . ? C19 C24 H24A 109.5 . . ? C19 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C19 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C21 C25 H25A 109.5 . . ? C21 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C21 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C6 N1 C7 109.1(2) . . ? C6 N1 C9 126.3(2) . . ? C7 N1 C9 124.5(2) . . ? C6 N2 C8 108.7(2) . . ? C6 N2 C18 127.1(2) . . ? C8 N2 C18 124.2(2) . . ? C2 V1 C1 36.2(2) . . ? C2 V1 C3 35.32(17) . . ? C1 V1 C3 58.47(16) . . ? C2 V1 C5 59.1(2) . . ? C1 V1 C5 35.2(3) . . ? C3 V1 C5 57.42(16) . . ? C2 V1 C4 58.56(17) . . ? C1 V1 C4 57.8(2) . . ? C3 V1 C4 34.54(16) . . ? C5 V1 C4 34.0(2) . . ? C2 V1 Cl3 146.52(12) . . ? C1 V1 Cl3 131.5(3) . . ? C3 V1 Cl3 113.10(13) . . ? C5 V1 Cl3 97.4(2) . . ? C4 V1 Cl3 88.44(13) . . ? C2 V1 Cl2 106.30(14) . . ? C1 V1 Cl2 88.12(12) . . ? C3 V1 Cl2 141.50(12) . . ? C5 V1 Cl2 106.8(2) . . ? C4 V1 Cl2 140.69(15) . . ? Cl3 V1 Cl2 103.19(4) . . ? C2 V1 Cl1 96.50(16) . . ? C1 V1 Cl1 130.5(3) . . ? C3 V1 Cl1 92.10(11) . . ? C5 V1 Cl1 149.52(14) . . ? C4 V1 Cl1 119.40(15) . . ? Cl3 V1 Cl1 95.25(5) . . ? Cl2 V1 Cl1 97.09(4) . . ? 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 C5 C1 C2 C3 -1.1(5) . . . . ? V1 C1 C2 C3 -66.1(3) . . . . ? C5 C1 C2 V1 64.9(4) . . . . ? C1 C2 C3 C4 1.3(5) . . . . ? V1 C2 C3 C4 -64.3(3) . . . . ? C1 C2 C3 V1 65.6(3) . . . . ? C2 C3 C4 C5 -1.0(5) . . . . ? V1 C3 C4 C5 -64.0(3) . . . . ? C2 C3 C4 V1 63.0(3) . . . . ? C3 C4 C5 C1 0.2(6) . . . . ? V1 C4 C5 C1 -63.2(4) . . . . ? C3 C4 C5 V1 63.4(3) . . . . ? C2 C1 C5 C4 0.5(6) . . . . ? V1 C1 C5 C4 64.2(4) . . . . ? C2 C1 C5 V1 -63.7(3) . . . . ? N1 C7 C8 N2 -0.2(4) . . . . ? C14 C9 C10 C11 -0.1(4) . . . . ? N1 C9 C10 C11 -178.4(2) . . . . ? C14 C9 C10 C15 180.0(3) . . . . ? N1 C9 C10 C15 1.8(4) . . . . ? C9 C10 C11 C12 1.8(4) . . . . ? C15 C10 C11 C12 -178.3(3) . . . . ? C10 C11 C12 C13 -1.0(5) . . . . ? C10 C11 C12 C16 179.2(3) . . . . ? C11 C12 C13 C14 -1.5(5) . . . . ? C16 C12 C13 C14 178.2(3) . . . . ? C10 C9 C14 C13 -2.2(4) . . . . ? N1 C9 C14 C13 176.1(3) . . . . ? C10 C9 C14 C17 176.3(3) . . . . ? N1 C9 C14 C17 -5.5(4) . . . . ? C12 C13 C14 C9 3.0(5) . . . . ? C12 C13 C14 C17 -175.4(3) . . . . ? C23 C18 C19 C20 -0.8(5) . . . . ? N2 C18 C19 C20 176.5(3) . . . . ? C23 C18 C19 C24 179.6(3) . . . . ? N2 C18 C19 C24 -3.1(4) . . . . ? C18 C19 C20 C21 0.5(5) . . . . ? C24 C19 C20 C21 -179.9(3) . . . . ? C19 C20 C21 C22 -0.1(5) . . . . ? C19 C20 C21 C25 179.0(4) . . . . ? C20 C21 C22 C23 -0.1(5) . . . . ? C25 C21 C22 C23 -179.2(4) . . . . ? C21 C22 C23 C18 -0.2(5) . . . . ? C21 C22 C23 C26 178.9(3) . . . . ? C19 C18 C23 C22 0.6(4) . . . . ? N2 C18 C23 C22 -176.7(3) . . . . ? C19 C18 C23 C26 -178.4(3) . . . . ? N2 C18 C23 C26 4.3(4) . . . . ? N2 C6 N1 C7 0.0(3) . . . . ? N2 C6 N1 C9 176.6(3) . . . . ? C8 C7 N1 C6 0.1(4) . . . . ? C8 C7 N1 C9 -176.6(3) . . . . ? C14 C9 N1 C6 108.4(3) . . . . ? C10 C9 N1 C6 -73.2(4) . . . . ? C14 C9 N1 C7 -75.5(4) . . . . ? C10 C9 N1 C7 102.9(3) . . . . ? N1 C6 N2 C8 -0.1(3) . . . . ? N1 C6 N2 C18 -179.8(3) . . . . ? C7 C8 N2 C6 0.2(4) . . . . ? C7 C8 N2 C18 179.9(3) . . . . ? C19 C18 N2 C6 94.2(4) . . . . ? C23 C18 N2 C6 -88.4(4) . . . . ? C19 C18 N2 C8 -85.5(4) . . . . ? C23 C18 N2 C8 92.0(4) . . . . ? C3 C2 V1 C1 113.4(5) . . . . ? C1 C2 V1 C3 -113.4(5) . . . . ? C3 C2 V1 C5 76.1(4) . . . . ? C1 C2 V1 C5 -37.4(3) . . . . ? C3 C2 V1 C4 36.2(3) . . . . ? C1 C2 V1 C4 -77.3(4) . . . . ? C3 C2 V1 Cl3 25.4(5) . . . . ? C1 C2 V1 Cl3 -88.1(5) . . . . ? C3 C2 V1 Cl2 176.2(3) . . . . ? C1 C2 V1 Cl2 62.8(4) . . . . ? C3 C2 V1 Cl1 -84.4(3) . . . . ? C1 C2 V1 Cl1 162.1(4) . . . . ? C5 C1 V1 C2 -115.4(4) . . . . ? C5 C1 V1 C3 -76.9(3) . . . . ? C2 C1 V1 C3 38.5(3) . . . . ? C2 C1 V1 C5 115.4(4) . . . . ? C5 C1 V1 C4 -36.0(3) . . . . ? C2 C1 V1 C4 79.4(3) . . . . ? C5 C1 V1 Cl3 17.2(4) . . . . ? C2 C1 V1 Cl3 132.6(4) . . . . ? C5 C1 V1 Cl2 123.2(4) . . . . ? C2 C1 V1 Cl2 -121.4(4) . . . . ? C5 C1 V1 Cl1 -139.1(4) . . . . ? C2 C1 V1 Cl1 -23.7(5) . . . . ? C4 C3 V1 C2 117.3(4) . . . . ? C4 C3 V1 C1 77.9(4) . . . . ? C2 C3 V1 C1 -39.4(4) . . . . ? C4 C3 V1 C5 36.1(4) . . . . ? C2 C3 V1 C5 -81.2(4) . . . . ? C2 C3 V1 C4 -117.3(4) . . . . ? C4 C3 V1 Cl3 -47.8(3) . . . . ? C2 C3 V1 Cl3 -165.1(3) . . . . ? C4 C3 V1 Cl2 111.5(3) . . . . ? C2 C3 V1 Cl2 -5.9(4) . . . . ? C4 C3 V1 Cl1 -144.4(3) . . . . ? C2 C3 V1 Cl1 98.3(3) . . . . ? C4 C5 V1 C2 -78.5(4) . . . . ? C1 C5 V1 C2 38.4(3) . . . . ? C4 C5 V1 C1 -116.9(5) . . . . ? C4 C5 V1 C3 -36.8(3) . . . . ? C1 C5 V1 C3 80.2(4) . . . . ? C1 C5 V1 C4 116.9(5) . . . . ? C4 C5 V1 Cl3 76.0(4) . . . . ? C1 C5 V1 Cl3 -167.1(4) . . . . ? C4 C5 V1 Cl2 -177.8(3) . . . . ? C1 C5 V1 Cl2 -60.9(4) . . . . ? C4 C5 V1 Cl1 -37.8(8) . . . . ? C1 C5 V1 Cl1 79.2(7) . . . . ? C5 C4 V1 C2 80.2(4) . . . . ? C3 C4 V1 C2 -37.0(3) . . . . ? C5 C4 V1 C1 37.4(4) . . . . ? C3 C4 V1 C1 -79.8(4) . . . . ? C5 C4 V1 C3 117.2(5) . . . . ? C3 C4 V1 C5 -117.2(5) . . . . ? C5 C4 V1 Cl3 -105.7(4) . . . . ? C3 C4 V1 Cl3 137.0(3) . . . . ? C5 C4 V1 Cl2 3.4(5) . . . . ? C3 C4 V1 Cl2 -113.9(3) . . . . ? C5 C4 V1 Cl1 159.1(4) . . . . ? C3 C4 V1 Cl1 41.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.439 _refine_diff_density_min -0.392 _refine_diff_density_rms 0.093 # start Validation Reply Form _vrf_PLAT602_shelxl ; PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure ! RESPONSE: A badly disordered molecule of toluene was removed using the squeeze function in platon ; # end Validation Reply Form # Attachment '[IMes]+[CpV_N_Cl2]-_Dalton.cif' data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 752794' #TrackingRef '[IMes]+[CpV_N_Cl2]-_Dalton.cif' _audit_update_record ; 2009-10-28 # Formatted by publCIF ; _audit_creation_date 06-08-13 _audit_creation_method CRYSTALS_ver_12.84 _cell_length_a 8.3520(17) _cell_length_b 8.7980(18) _cell_length_c 18.550(4) _cell_angle_alpha 79.78(3) _cell_angle_beta 89.34(3) _cell_angle_gamma 72.16(3) _cell_volume 1275.6(5) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' V 0.3005 0.5294 10.2971 6.8657 7.3511 0.4385 2.0703 26.8938 2.0571 102.4780 1.2199 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Ag -0.8971 1.1015 19.2808 0.6446 16.6885 7.4726 4.8045 24.6605 1.0463 99.8156 5.1790 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Found Formula = C26 H30 Cl2 N3 V1 # Dc = 1.32 FOOO = 528.00 Mu = 6.17 M = 506.39 _chemical_formula_sum 'C26 H30 Cl2 N3 V1' _chemical_formula_moiety 'C26 H30 Cl2 N3 V1' _chemical_compound_source ? _chemical_formula_weight 506.39 _cell_measurement_reflns_used 8857 _cell_measurement_theta_min 2 _cell_measurement_theta_max 30 _cell_measurement_temperature 120 _exptl_crystal_description prism _exptl_crystal_colour 'light blue' _exptl_crystal_size_min 0.34 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_max 0.56 _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_meas ? _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.617 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8009 _exptl_absorpt_correction_T_max 0.8109 _diffrn_measurement_device_type 'Bruker SMART' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material CRYSTALS _computing_molecular_graphics 'ORTEP-3 For Windows (Farrugia L.J., 1997)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 120 _diffrn_reflns_number 7456 _reflns_number_total 7433 _diffrn_reflns_av_R_equivalents 0.023 # Number of reflections with Friedels Law is 7433 # Number of reflections without Friedels Law is 12928 # Theoretical number of reflections is about 7456 _diffrn_reflns_theta_min 2.234 _diffrn_reflns_theta_max 30.021 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.021 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min -12 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 26 _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.39 _refine_diff_density_max 1.06 _refine_ls_number_reflns 7415 _refine_ls_number_restraints 0 _refine_ls_number_parameters 290 _refine_ls_wR_factor_ref 0.1000 _refine_ls_goodness_of_fit_ref 0.9386 _refine_ls_R_factor_all 0.0404 _refine_ls_wR_factor_all 0.1000 _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 6439 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_gt 0.0931 _refine_ls_shift/su_max 3.705321 _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment refall _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 53.1 87.8 52.0 21.3 4.69 ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The H atoms were placed in their calculated positions (CRYSTALS, Watkin, D.L. et al. 1994) after which the positions were refined with riding constraints. ; _publ_section_exptl_prep ; (type here to add preparation details) ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435--?. Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487--?. CambridgeSoft Corp., (2002). 100 CambridgePark Drive, Cambridge, MA 02140. Cromer, D.T. and Mann, J.B., Acta Cryst. A24, 321-324 (1968). Cromer, D. T. & Waber, J. T.; "International Tables for X-ray Crystallography", Vol. IV, The Kynoch Press, Birmingham, England, Table 2.2 A (1974). Creagh, D. C. & McAuley, W.J .; "International Tables for Crystallography", Vol C, (A.J.C. Wilson, ed.), Kluwer Academic Publishers, Boston, Table 4.2.6.8, pages 219-222 (1992). Creagh, D. C. & Hubbell, J.H..; "International Tables for Crystallography", Vol C, (A.J.C. Wilson, ed.), Kluwer Academic Publishers, Boston, Table 4.2.4.3, pages 200-206 (1992). Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565--?. Larson, A. C. (1970). Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Watkin, D. J. (1994). Acta Cryst. A50, 411--437. ; 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens V1 V 0.16490(3) 0.79522(2) 0.695532(12) 0.0143 1.0000 Uani . . . . . . Cl1 Cl 0.22171(4) 0.52622(4) 0.67987(2) 0.0225 1.0000 Uani . . . . . . Cl2 Cl 0.32524(5) 0.73379(4) 0.806519(17) 0.0222 1.0000 Uani . . . . . . N1 N 0.49657(16) 0.21492(14) 0.85243(7) 0.0219 1.0000 Uani . . . . . . N2 N 0.63520(15) 0.27353(14) 0.75726(6) 0.0190 1.0000 Uani . . . . . . N3 N -0.02814(13) 0.84315(13) 0.72031(6) 0.0173 1.0000 Uani . . . . . . C1 C 0.51257(16) 0.33540(15) 0.80085(7) 0.0169 1.0000 Uani . . . . . . C2 C 0.6129(3) 0.07060(19) 0.84143(10) 0.0384 1.0000 Uani . . . . . . C3 C 0.7003(2) 0.10707(19) 0.78212(10) 0.0340 1.0000 Uani . . . . . . C4 C 0.37825(17) 0.23383(16) 0.91032(7) 0.0193 1.0000 Uani . . . . . . C5 C 0.42548(18) 0.27301(17) 0.97484(8) 0.0214 1.0000 Uani . . . . . . C6 C 0.30814(18) 0.29382(18) 1.02966(7) 0.0214 1.0000 Uani . . . . . . C7 C 0.15039(18) 0.27230(17) 1.02138(7) 0.0205 1.0000 Uani . . . . . . C8 C 0.11104(18) 0.22940(17) 0.95638(8) 0.0219 1.0000 Uani . . . . . . C9 C 0.22222(18) 0.21056(16) 0.89928(8) 0.0205 1.0000 Uani . . . . . . C10 C 0.5981(2) 0.2898(3) 0.98597(10) 0.0338 1.0000 Uani . . . . . . C11 C 0.0253(2) 0.2936(2) 1.08128(8) 0.0287 1.0000 Uani . . . . . . C12 C 0.1767(2) 0.1678(2) 0.82872(9) 0.0296 1.0000 Uani . . . . . . C13 C 0.68688(16) 0.36758(15) 0.69430(7) 0.0160 1.0000 Uani . . . . . . C14 C 0.75585(16) 0.48870(17) 0.70573(7) 0.0185 1.0000 Uani . . . . . . C15 C 0.79720(17) 0.58284(17) 0.64382(8) 0.0197 1.0000 Uani . . . . . . C16 C 0.77297(16) 0.55800(16) 0.57309(7) 0.0187 1.0000 Uani . . . . . . C17 C 0.70586(17) 0.43457(17) 0.56430(7) 0.0185 1.0000 Uani . . . . . . C18 C 0.66062(16) 0.33784(16) 0.62432(7) 0.0170 1.0000 Uani . . . . . . C19 C 0.7864(2) 0.5212(2) 0.78073(8) 0.0274 1.0000 Uani . . . . . . C20 C 0.8175(2) 0.6641(2) 0.50758(9) 0.0277 1.0000 Uani . . . . . . C21 C 0.5839(2) 0.20844(19) 0.61312(9) 0.0265 1.0000 Uani . . . . . . C22 C 0.3718(2) 0.9165(2) 0.64425(9) 0.0322 1.0000 Uani . . . . . . C23 C 0.2174(3) 1.0379(2) 0.65100(9) 0.0345 1.0000 Uani . . . . . . C24 C 0.0942(2) 1.02092(19) 0.60339(8) 0.0276 1.0000 Uani . . . . . . C25 C 0.1721(2) 0.88367(19) 0.57150(8) 0.0236 1.0000 Uani . . . . . . C26 C 0.34481(19) 0.8227(2) 0.59586(8) 0.0269 1.0000 Uani . . . . . . H33 H 0.4487 0.4463 0.7962 0.0204 1.0000 Uiso R . . . . . H34 H 0.8436 0.6649 0.6500 0.0255 1.0000 Uiso R . . . . . H35 H 0.6890 0.4170 0.5159 0.0235 1.0000 Uiso R . . . . . H36 H 0.0066 0.2097 0.9507 0.0264 1.0000 Uiso R . . . . . H37 H 0.1187 0.8409 0.5361 0.0302 1.0000 Uiso R . . . . . H38 H 0.7854 0.0382 0.7600 0.0356 1.0000 Uiso R . . . . . H39 H 0.6220 -0.0276 0.8702 0.0412 1.0000 Uiso R . . . . . H40 H 0.3372 0.3209 1.0745 0.0264 1.0000 Uiso R . . . . . H41 H 0.2018 1.1227 0.6796 0.0455 1.0000 Uiso R . . . . . H42 H 0.4294 0.7265 0.5821 0.0343 1.0000 Uiso R . . . . . H43 H -0.0234 1.0909 0.5938 0.0338 1.0000 Uiso R . . . . . H44 H 0.4779 0.8967 0.6729 0.0432 1.0000 Uiso R . . . . . H45 H 0.6823 0.1938 0.9789 0.0536 1.0000 Uiso R . . . . . H46 H 0.6106 0.3800 0.9490 0.0524 1.0000 Uiso R . . . . . H47 H 0.0787 0.2647 1.1288 0.0445 1.0000 Uiso R . . . . . H48 H -0.0408 0.2241 1.0792 0.0467 1.0000 Uiso R . . . . . H49 H -0.0481 0.3999 1.0754 0.0462 1.0000 Uiso R . . . . . H50 H 0.2571 0.0702 0.8193 0.0469 1.0000 Uiso R . . . . . H51 H 0.8141 0.4227 0.8163 0.0437 1.0000 Uiso R . . . . . H52 H 0.6873 0.5961 0.7971 0.0440 1.0000 Uiso R . . . . . H53 H 0.9314 0.6623 0.5138 0.0433 1.0000 Uiso R . . . . . H54 H 0.8067 0.6248 0.4629 0.0432 1.0000 Uiso R . . . . . H55 H 0.7443 0.7738 0.5048 0.0434 1.0000 Uiso R . . . . . H56 H 0.5565 0.2227 0.5610 0.0468 1.0000 Uiso R . . . . . H57 H 0.6633 0.1019 0.6287 0.0472 1.0000 Uiso R . . . . . H58 H 0.4824 0.2198 0.6404 0.0464 1.0000 Uiso R . . . . . H59 H 0.1742 0.2551 0.7871 0.0460 1.0000 Uiso R . . . . . H60 H 0.6106 0.3084 1.0353 0.0527 1.0000 Uiso R . . . . . H61 H 0.8788 0.5635 0.7801 0.0443 1.0000 Uiso R . . . . . H62 H 0.0666 0.1514 0.8317 0.0474 1.0000 Uiso R . . . . . 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 0.01423(10) 0.01253(10) 0.01564(10) -0.00324(7) 0.00322(7) -0.00308(7) Cl1 0.01981(15) 0.01512(14) 0.03266(17) -0.00840(12) -0.00254(12) -0.00308(11) Cl2 0.03075(17) 0.01731(14) 0.01566(14) -0.00401(10) -0.00055(11) -0.00275(12) N1 0.0235(5) 0.0147(5) 0.0210(5) 0.0013(4) 0.0085(4) 0.0008(4) N2 0.0197(5) 0.0152(5) 0.0186(5) -0.0008(4) 0.0062(4) -0.0017(4) N3 0.0112(4) 0.0137(4) 0.0242(5) -0.0037(4) 0.0076(4) 0.0001(4) C1 0.0168(5) 0.0147(5) 0.0171(5) -0.0011(4) 0.0032(4) -0.0030(4) C2 0.0462(10) 0.0148(6) 0.0381(9) 0.0049(6) 0.0230(8) 0.0077(6) C3 0.0364(8) 0.0163(6) 0.0355(8) 0.0024(6) 0.0174(7) 0.0073(6) C4 0.0212(6) 0.0156(5) 0.0170(5) 0.0007(4) 0.0063(4) -0.0019(4) C5 0.0208(6) 0.0221(6) 0.0183(6) 0.0014(5) 0.0023(5) -0.0053(5) C6 0.0240(6) 0.0238(6) 0.0148(5) -0.0002(5) 0.0021(5) -0.0067(5) C7 0.0219(6) 0.0205(6) 0.0164(6) -0.0008(4) 0.0049(5) -0.0041(5) C8 0.0217(6) 0.0223(6) 0.0215(6) -0.0039(5) 0.0040(5) -0.0066(5) C9 0.0252(6) 0.0164(5) 0.0184(6) -0.0026(4) 0.0038(5) -0.0048(5) C10 0.0244(7) 0.0491(10) 0.0290(8) -0.0024(7) 0.0019(6) -0.0157(7) C11 0.0261(7) 0.0369(8) 0.0205(6) -0.0043(6) 0.0094(5) -0.0068(6) C12 0.0396(9) 0.0288(7) 0.0238(7) -0.0116(6) 0.0038(6) -0.0118(6) C13 0.0142(5) 0.0166(5) 0.0163(5) -0.0024(4) 0.0040(4) -0.0038(4) C14 0.0145(5) 0.0226(6) 0.0187(6) -0.0056(5) 0.0007(4) -0.0050(4) C15 0.0161(5) 0.0213(6) 0.0243(6) -0.0054(5) 0.0016(5) -0.0090(5) C16 0.0153(5) 0.0200(6) 0.0204(6) -0.0016(5) 0.0035(4) -0.0062(4) C17 0.0179(5) 0.0214(6) 0.0172(5) -0.0052(4) 0.0037(4) -0.0068(5) C18 0.0156(5) 0.0178(5) 0.0195(6) -0.0059(4) 0.0047(4) -0.0064(4) C19 0.0273(7) 0.0372(8) 0.0218(6) -0.0108(6) -0.0001(5) -0.0126(6) C20 0.0308(7) 0.0273(7) 0.0258(7) 0.0013(5) 0.0067(6) -0.0136(6) C21 0.0299(7) 0.0268(7) 0.0315(7) -0.0128(6) 0.0099(6) -0.0175(6) C22 0.0365(8) 0.0425(9) 0.0244(7) 0.0051(6) -0.0028(6) -0.0279(7) C23 0.0681(12) 0.0236(7) 0.0200(7) -0.0042(5) 0.0074(7) -0.0263(8) C24 0.0345(8) 0.0208(6) 0.0196(6) 0.0043(5) 0.0044(5) -0.0016(6) C25 0.0287(7) 0.0275(7) 0.0148(6) -0.0034(5) 0.0001(5) -0.0090(5) C26 0.0228(7) 0.0340(8) 0.0220(6) -0.0015(6) 0.0072(5) -0.0082(6) _refine_ls_extinction_coef -32(9) _refine_ls_extinction_method 'Larson (1970), Equation 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag V1 . Cl1 . 2.3375(7) yes V1 . Cl2 . 2.3557(9) yes V1 . N3 . 1.6198(11) yes V1 . C22 . 2.4004(17) yes V1 . C23 . 2.3177(16) yes V1 . C24 . 2.3051(17) yes V1 . C25 . 2.3006(15) yes V1 . C26 . 2.3947(16) yes N1 . C1 . 1.3345(17) yes N1 . C2 . 1.3892(19) yes N1 . C4 . 1.4477(17) yes N2 . C1 . 1.3397(17) yes N2 . C3 . 1.3898(19) yes N2 . C13 . 1.4489(17) yes C1 . H33 . 0.947 no C2 . C3 . 1.359(2) yes C2 . H39 . 0.913 no C3 . H38 . 0.927 no C4 . C5 . 1.395(2) yes C4 . C9 . 1.402(2) yes C5 . C6 . 1.4006(19) yes C5 . C10 . 1.513(2) yes C6 . C7 . 1.401(2) yes C6 . H40 . 0.958 no C7 . C8 . 1.397(2) yes C7 . C11 . 1.513(2) yes C8 . C9 . 1.3989(19) yes C8 . H36 . 0.951 no C9 . C12 . 1.508(2) yes C10 . H45 . 0.948 no C10 . H46 . 0.984 no C10 . H60 . 0.971 no C11 . H47 . 0.949 no C11 . H48 . 0.947 no C11 . H49 . 0.937 no C12 . H50 . 0.958 no C12 . H59 . 0.984 no C12 . H62 . 0.973 no C13 . C14 . 1.4040(18) yes C13 . C18 . 1.4015(18) yes C14 . C15 . 1.3974(19) yes C14 . C19 . 1.509(2) yes C15 . C16 . 1.3947(19) yes C15 . H34 . 0.941 no C16 . C17 . 1.3993(19) yes C16 . C20 . 1.512(2) yes C17 . C18 . 1.3991(18) yes C17 . H35 . 0.956 no C18 . C21 . 1.5113(19) yes C19 . H51 . 0.958 no C19 . H52 . 0.971 no C19 . H61 . 0.953 no C20 . H53 . 0.954 no C20 . H54 . 0.967 no C20 . H55 . 0.964 no C21 . H56 . 0.974 no C21 . H57 . 0.964 no C21 . H58 . 0.970 no C22 . C23 . 1.421(3) yes C22 . C26 . 1.385(2) yes C22 . H44 . 0.991 no C23 . C24 . 1.422(3) yes C23 . H41 . 0.967 no C24 . C25 . 1.412(2) yes C24 . H43 . 0.985 no C25 . C26 . 1.424(2) yes C25 . H37 . 0.984 no C26 . H42 . 0.994 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag Cl1 . V1 . Cl2 . 95.87(4) yes Cl1 . V1 . N3 . 103.33(5) yes Cl2 . V1 . N3 . 103.99(5) yes Cl1 . V1 . C22 . 113.01(6) yes Cl2 . V1 . C22 . 85.56(5) yes N3 . V1 . C22 . 141.31(7) yes Cl1 . V1 . C23 . 143.97(5) yes Cl2 . V1 . C23 . 96.39(6) yes N3 . V1 . C23 . 106.31(8) yes C22 . V1 . C23 . 35.00(7) yes Cl1 . V1 . C24 . 125.88(5) yes Cl2 . V1 . C24 . 131.84(5) yes N3 . V1 . C24 . 89.85(8) yes C22 . V1 . C24 . 58.44(7) yes C23 . V1 . C24 . 35.84(7) yes Cl1 . V1 . C25 . 91.72(6) yes Cl2 . V1 . C25 . 142.46(4) yes N3 . V1 . C25 . 109.89(7) yes C22 . V1 . C25 . 57.83(6) yes C23 . V1 . C25 . 59.15(6) yes Cl1 . V1 . C26 . 86.18(5) yes Cl2 . V1 . C26 . 108.63(5) yes N3 . V1 . C26 . 144.86(6) yes C22 . V1 . C26 . 33.59(6) yes C23 . V1 . C26 . 57.79(7) yes C24 . V1 . C25 . 35.71(6) yes C24 . V1 . C26 . 58.54(6) yes C25 . V1 . C26 . 35.25(6) yes C1 . N1 . C2 . 108.59(12) yes C1 . N1 . C4 . 125.10(12) yes C2 . N1 . C4 . 126.30(12) yes C1 . N2 . C3 . 108.71(12) yes C1 . N2 . C13 . 124.52(11) yes C3 . N2 . C13 . 126.77(12) yes N2 . C1 . N1 . 108.65(12) yes N2 . C1 . H33 . 125.7 no N1 . C1 . H33 . 125.6 no N1 . C2 . C3 . 107.27(13) yes N1 . C2 . H39 . 123.1 no C3 . C2 . H39 . 129.6 no N2 . C3 . C2 . 106.78(13) yes N2 . C3 . H38 . 124.2 no C2 . C3 . H38 . 129.0 no N1 . C4 . C5 . 118.40(13) yes N1 . C4 . C9 . 118.56(13) yes C5 . C4 . C9 . 123.04(13) yes C4 . C5 . C6 . 117.57(13) yes C4 . C5 . C10 . 121.43(13) yes C6 . C5 . C10 . 120.99(14) yes C5 . C6 . C7 . 121.67(13) yes C5 . C6 . H40 . 119.4 no C7 . C6 . H40 . 119.0 no C6 . C7 . C8 . 118.40(13) yes C6 . C7 . C11 . 121.18(14) yes C8 . C7 . C11 . 120.41(14) yes C7 . C8 . C9 . 122.21(14) yes C7 . C8 . H36 . 119.6 no C9 . C8 . H36 . 118.2 no C4 . C9 . C8 . 117.08(13) yes C4 . C9 . C12 . 121.24(13) yes C8 . C9 . C12 . 121.67(14) yes C5 . C10 . H45 . 109.8 no C5 . C10 . H46 . 108.8 no H45 . C10 . H46 . 107.7 no C5 . C10 . H60 . 109.3 no H45 . C10 . H60 . 109.8 no H46 . C10 . H60 . 111.3 no C7 . C11 . H47 . 112.5 no C7 . C11 . H48 . 108.6 no H47 . C11 . H48 . 107.2 no C7 . C11 . H49 . 112.2 no H47 . C11 . H49 . 108.8 no H48 . C11 . H49 . 107.5 no C9 . C12 . H50 . 111.2 no C9 . C12 . H59 . 110.5 no H50 . C12 . H59 . 107.7 no C9 . C12 . H62 . 109.8 no H50 . C12 . H62 . 108.3 no H59 . C12 . H62 . 109.2 no N2 . C13 . C14 . 118.59(12) yes N2 . C13 . C18 . 118.69(12) yes C14 . C13 . C18 . 122.69(12) yes C13 . C14 . C15 . 117.44(12) yes C13 . C14 . C19 . 123.32(13) yes C15 . C14 . C19 . 119.24(13) yes C14 . C15 . C16 . 121.93(12) yes C14 . C15 . H34 . 119.1 no C16 . C15 . H34 . 118.9 no C15 . C16 . C17 . 118.71(12) yes C15 . C16 . C20 . 120.15(13) yes C17 . C16 . C20 . 121.14(13) yes C16 . C17 . C18 . 121.74(12) yes C16 . C17 . H35 . 119.1 no C18 . C17 . H35 . 119.2 no C13 . C18 . C17 . 117.49(12) yes C13 . C18 . C21 . 121.86(12) yes C17 . C18 . C21 . 120.64(12) yes C14 . C19 . H51 . 110.5 no C14 . C19 . H52 . 111.8 no H51 . C19 . H52 . 106.9 no C14 . C19 . H61 . 109.7 no H51 . C19 . H61 . 107.8 no H52 . C19 . H61 . 109.9 no C16 . C20 . H53 . 109.4 no C16 . C20 . H54 . 110.8 no H53 . C20 . H54 . 108.3 no C16 . C20 . H55 . 108.5 no H53 . C20 . H55 . 109.0 no H54 . C20 . H55 . 110.8 no C18 . C21 . H56 . 108.2 no C18 . C21 . H57 . 110.4 no H56 . C21 . H57 . 108.5 no C18 . C21 . H58 . 109.7 no H56 . C21 . H58 . 109.8 no H57 . C21 . H58 . 110.3 no V1 . C22 . C23 . 69.32(9) yes V1 . C22 . C26 . 72.98(9) yes C23 . C22 . C26 . 108.53(15) yes V1 . C22 . H44 . 119.4 no C23 . C22 . H44 . 125.3 no C26 . C22 . H44 . 126.0 no C22 . C23 . V1 . 75.68(9) yes C22 . C23 . C24 . 107.89(14) yes V1 . C23 . C24 . 71.60(9) yes C22 . C23 . H41 . 125.8 no V1 . C23 . H41 . 122.6 no C24 . C23 . H41 . 126.1 no V1 . C24 . C23 . 72.56(9) yes V1 . C24 . C25 . 71.97(9) yes C23 . C24 . C25 . 107.06(15) yes V1 . C24 . H43 . 121.0 no C23 . C24 . H43 . 127.2 no C25 . C24 . H43 . 125.8 no V1 . C25 . C24 . 72.32(9) yes V1 . C25 . C26 . 75.99(9) yes C24 . C25 . C26 . 108.29(14) yes V1 . C25 . H37 . 120.6 no C24 . C25 . H37 . 126.2 no C26 . C25 . H37 . 125.4 no C25 . C26 . C22 . 108.10(15) yes C25 . C26 . V1 . 68.77(9) yes C22 . C26 . V1 . 73.43(9) yes C25 . C26 . H42 . 125.6 no C22 . C26 . H42 . 126.3 no V1 . C26 . H42 . 121.4 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N2 . H38 . N3 1_645 156 2.06 2.17 4.131(2) yes