# 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