PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. Oct 1, 2012; 68(Pt 10): m1311–m1312.
Published online Sep 29, 2012. doi:  10.1107/S1600536812040251
PMCID: PMC3470179
cis-Chloridobis(4,4′-dimethyl-2,2′-bipyridine-κ2 N,N′)oxidovanadium(IV) chloride ethanol monosolvate monohydrate
Sadif A. Shirvan,a* Sara Haydari Dezfuli,a Elyas Golabi,b and Mohammad Amin Gholamzadehb
aDepartment of Chemistry, Islamic Azad University, Omidieh Branch, Omidieh, Iran
bDepartment of Petroleum Engineering, Islamic Azad University, Omidieh Branch, Omidieh, Iran
Correspondence e-mail: sadif_shirvan1/at/yahoo.com
Received September 9, 2012; Accepted September 22, 2012.
Abstract
In the title compound, [VClO(C12H12N2)2]Cl·C2H5OH·H2O, the VIV atom is six-coordinated in a distorted octa­hedral geometry by four N atoms from two 4,4′-dimethyl-2,2′-bipyridine ligands, one O atom and one Cl atom. In the crystal, O—H(...)Cl, C—H(...)O and C—H(...)Cl hydrogen bonds and π–π contacts between the pyridine rings [centroid–centroid distances = 3.7236 (17) and 3.6026 (19) Å] stabilize the structure. Intra­molecular C—H(...)O and C—H(...)Cl hydrogen bonds are also present.
Related literature  
For related structures, see: Ahmadi et al. (2008 [triangle]); Alizadeh et al. (2010 [triangle]); Amani et al. (2009 [triangle]); Hojjat Kashani et al. (2008 [triangle]); Kalateh et al. (2008 [triangle], 2010 [triangle]); Shirvan & Haydari Dezfuli (2011 [triangle], 2012a [triangle],b [triangle]); Triantafillou et al. (2004 [triangle]); Yousefi et al. (2008 [triangle]).
An external file that holds a picture, illustration, etc.
Object name is e-68-m1311-scheme1.jpg Object name is e-68-m1311-scheme1.jpg
Crystal data  
  • [VClO(C12H12N2)2]Cl·C2H6O·H2O
  • M r = 570.40
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-68-m1311-efi1.jpg
  • a = 9.6955 (11) Å
  • b = 10.9905 (12) Å
  • c = 14.5739 (17) Å
  • α = 68.711 (2)°
  • β = 72.401 (2)°
  • γ = 81.381 (2)°
  • V = 1377.9 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.59 mm−1
  • T = 120 K
  • 0.32 × 0.14 × 0.09 mm
Data collection  
  • Bruker SMART 1000 CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.926, T max = 0.954
  • 12257 measured reflections
  • 5363 independent reflections
  • 4398 reflections with I > 2σ(I)
  • R int = 0.026
Refinement  
  • R[F 2 > 2σ(F 2)] = 0.062
  • wR(F 2) = 0.144
  • S = 1.00
  • 5363 reflections
  • 330 parameters
  • H-atom parameters constrained
  • Δρmax = 2.09 e Å−3
  • Δρmin = −0.89 e Å−3
Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]) and Mercury (Macrae et al., 2006 [triangle]); software used to prepare material for publication: SHELXTL.
Table 1
Table 1
Hydrogen-bond geometry (Å, °)
Supplementary Material
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812040251/hy2588sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040251/hy2588Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
We are grateful to the Islamic Azad University, Omidieh Branch, for financial support.
supplementary crystallographic information
Comment
Recently, we reported the synthesis and crystal structures of [In(4,4'-dmbipy)Cl3(MeOH)].MeOH, (II) (Shirvan & Haydari Dezfuli, 2012b), and [CdBr2(4,4'-dmbipy)(DMSO)], (III) (Shirvan & Haydari Dezfuli, 2012a) (4,4'-dmbipy = 4,4'-dimethyl-2,2'-bipyridine, DMSO = dimethyl sulfoxide). 4,4'-Dmbipy is a good bidentate ligand, and numerous complexes with 4,4'-dmbipy have been prepared, such as that of [Hg(4,4'-dmbipy)I2], (IV) (Yousefi et al., 2008), [Hg(4,4'-dmbipy)Br2], (V) (Kalateh et al., 2008), [Fe(4,4'-dmbipy)Cl3(DMSO)], (VI) (Amani et al., 2009), [Pt(4,4'-dmbipy)Cl4], (VII) (Hojjat Kashani et al., 2008), [Cd(4,4'-dmbipy)I2(DMSO)], (VIII) (Kalateh et al., 2010), [Zn(4,4'-dmbipy)Br2], (IX) (Alizadeh et al., 2010), [Zn(4,4'-dmbipy)(H2O)(NO3)2], (X) (Shirvan & Haydari Dezfuli, 2011) and [In(4,4'-dmbpy)Cl3(DMSO)], (XI) (Ahmadi et al., 2008). We report herein the synthesis and crystal structure of the title compound, (I).
In the title compound (Fig. 1), the VIV atom is six-coordinated in a distorted octahedral geometry by four N atoms from two 4,4'-dmbipy ligands, one O atom and one Cl atom. There are also one ethanol and one water solvent molecules in the asymmetric unit. The V—Cl, V—N and V—O bond lengths and angles are in good agreement with the corresponding values in [VOCl(dtbipy)Cl]Cl.CH2Cl2 (Triantafillou et al., 2004) (dtbipy = 4,4'-di-tert-butyl-2,2'-bipyridine).
In the crystal, intermolecular O—H···Cl, C—H···O and C—H···Cl hydrogen bonds, intramolecular C—H···O and C—H···Cl hydrogen bonds (Table 1) and π–π contacts between the pyridine rings (Fig. 2), Cg3···Cg4i and Cg5···Cg6ii, with centroid–centroid distances of 3.7236 (17) and 3.6026 (19) Å [symmetry codes: (i) 1-x, 1-y, 1-z; (ii) -x, 1-y, 2-z. Cg3, Cg4, Cg5 and Cg6 are the centroids of the N1/C1–C5, N2/C6–C10, N3/C13–C17 and N4/C18–C22 rings, respectively], stabilize the structure.
Experimental
For the preparation of the title compound, a solution of 4,4'-dimethyl-2,2'-bipyridine (0.29 g, 1.60 mmol) in ethanol (20 ml) was added to a solution of VCl3 (0.13 g, 0.80 mmol) in water (4 ml) and the resulting violet solution was stirred at 323 K for 40 min. Then, it was left to evaporate slowly at room temperature. After six days, green prismatic crystals of the title compound were isolated (yield: 0.32 g, 74.0%).
Refinement
H atoms bonded to C atoms were positioned geometrically and refined as riding atoms, with C—H = 0.95 (aromatic), 0.99 (CH2) and 0.98 (CH3) Å and with Uiso(H) = 1.2(1.5 for methyl)Ueq(C). H atoms of hydroxyl group and water molecules were located in a difference Fourier map and refined as riding atoms, with Uiso(H) = 1.2Ueq(O). There is a high residual peak of 2.09 e Å-3 near V1 atom due to the absorption effects that could not be correctly account for. The highest residual electron density was found at 0.84 Å from V1 atom and the deepest hole at 0.65 Å from V1 atom.
Figures
Fig. 1.
Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
Fig. 2.
Crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.
Crystal data
[VClO(C12H12N2)2]Cl·C2H6O·H2OZ = 2
Mr = 570.40F(000) = 594
Triclinic, P1Dx = 1.375 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.6955 (11) ÅCell parameters from 600 reflections
b = 10.9905 (12) Åθ = 3.0–26.0°
c = 14.5739 (17) ŵ = 0.59 mm1
α = 68.711 (2)°T = 120 K
β = 72.401 (2)°Prism, green
γ = 81.381 (2)°0.32 × 0.14 × 0.09 mm
V = 1377.9 (3) Å3
Data collection
Bruker SMART 1000 CCD diffractometer5363 independent reflections
Radiation source: fine-focus sealed tube4398 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
[var phi] and ω scansθmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.926, Tmax = 0.954k = −13→13
12257 measured reflectionsl = −17→17
Refinement
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.048P)2 + 3.916P] where P = (Fo2 + 2Fc2)/3
5363 reflections(Δ/σ)max < 0.001
330 parametersΔρmax = 2.09 e Å3
0 restraintsΔρmin = −0.89 e Å3
Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
xyzUiso*/Ueq
V10.17871 (6)0.53590 (5)0.73759 (4)0.02822 (16)
Cl10.10808 (9)0.45573 (9)0.63211 (6)0.0368 (2)
O10.0514 (2)0.6517 (2)0.74454 (15)0.0278 (5)
N10.3293 (3)0.6612 (3)0.61322 (19)0.0269 (6)
N20.3918 (3)0.4168 (2)0.71332 (19)0.0259 (6)
N40.0941 (3)0.3772 (3)0.86974 (19)0.0252 (5)
N30.2635 (3)0.5586 (3)0.84871 (18)0.0240 (5)
C10.2904 (4)0.7853 (3)0.5636 (2)0.0312 (7)
H1B0.19370.81620.58630.037*
C20.3840 (4)0.8699 (3)0.4815 (2)0.0327 (7)
H2A0.35250.95720.44960.039*
C30.5253 (4)0.8251 (3)0.4462 (2)0.0320 (7)
C40.5655 (4)0.6968 (3)0.4970 (2)0.0302 (7)
H4A0.66100.66340.47450.036*
C50.4672 (4)0.6175 (3)0.5801 (2)0.0263 (7)
C60.5039 (3)0.4814 (3)0.6387 (2)0.0260 (6)
C70.6429 (4)0.4240 (3)0.6201 (2)0.0301 (7)
H7A0.71950.47240.56740.036*
C80.6698 (4)0.2963 (3)0.6784 (2)0.0308 (7)
C90.5540 (4)0.2300 (3)0.7545 (2)0.0304 (7)
H9A0.56760.14220.79610.036*
C100.4187 (4)0.2928 (3)0.7691 (2)0.0279 (7)
H10A0.34060.24580.82130.033*
C110.6322 (4)0.9131 (4)0.3567 (3)0.0401 (9)
H11A0.59330.94580.29700.060*
H11B0.72390.86360.34120.060*
H11C0.64880.98700.37400.060*
C120.8190 (4)0.2308 (4)0.6607 (3)0.0419 (9)
H12A0.88570.27760.67350.063*
H12B0.85310.23210.58980.063*
H12C0.81510.14010.70720.063*
C130.3489 (3)0.6528 (3)0.8329 (2)0.0271 (7)
H13A0.38650.70920.76480.033*
C140.3850 (3)0.6718 (3)0.9109 (2)0.0290 (7)
H14A0.44620.74010.89640.035*
C150.3314 (3)0.5907 (3)1.0113 (2)0.0284 (7)
C160.2466 (3)0.4899 (3)1.0274 (2)0.0268 (7)
H16A0.21110.43041.09450.032*
C170.2136 (3)0.4755 (3)0.9458 (2)0.0235 (6)
C180.1223 (3)0.3723 (3)0.9571 (2)0.0229 (6)
C190.0696 (3)0.2746 (3)1.0491 (2)0.0267 (6)
H19A0.09200.27221.10880.032*
C20−0.0157 (3)0.1802 (3)1.0546 (2)0.0284 (7)
C21−0.0451 (3)0.1869 (3)0.9656 (3)0.0309 (7)
H21A−0.10360.12430.96630.037*
C220.0116 (3)0.2859 (3)0.8754 (2)0.0291 (7)
H22A−0.00900.28920.81480.035*
C230.3648 (4)0.6126 (4)1.0986 (3)0.0380 (8)
H23A0.30520.55701.16370.057*
H23B0.34340.70461.09330.057*
H23C0.46750.59051.09550.057*
C24−0.0717 (4)0.0744 (3)1.1545 (3)0.0384 (8)
H24A−0.14470.02711.14830.058*
H24B−0.11560.11331.20800.058*
H24C0.00850.01351.17240.058*
Cl20.35132 (10)0.10613 (9)0.13262 (9)0.0482 (3)
O1S0.3730 (3)0.1709 (3)0.3197 (2)0.0526 (7)
H1S0.34800.13800.27670.063*
O1W0.3211 (3)0.0038 (3)0.9589 (2)0.0505 (7)
H1W0.29640.03151.00880.061*
H2W0.4102−0.02470.92680.061*
C1S0.2544 (5)0.2599 (4)0.3334 (3)0.0511 (10)
H1SA0.21620.29010.27260.061*
H1SB0.28770.33710.33910.061*
C2S0.1359 (5)0.2007 (6)0.4266 (3)0.0722 (15)
H2SA0.06150.26850.43820.108*
H2SB0.17560.16200.48590.108*
H2SC0.09270.13260.41700.108*
Atomic displacement parameters (Å2)
U11U22U33U12U13U23
V10.0275 (3)0.0332 (3)0.0219 (3)−0.0078 (2)−0.0058 (2)−0.0050 (2)
Cl10.0360 (5)0.0488 (5)0.0279 (4)−0.0096 (4)−0.0037 (3)−0.0165 (4)
O10.0276 (11)0.0311 (11)0.0173 (10)−0.0014 (9)0.0052 (8)−0.0089 (9)
N10.0318 (14)0.0295 (14)0.0196 (12)−0.0053 (11)−0.0031 (11)−0.0102 (11)
N20.0328 (14)0.0264 (13)0.0188 (12)−0.0083 (11)−0.0039 (11)−0.0078 (10)
N40.0222 (13)0.0311 (14)0.0208 (12)−0.0054 (10)−0.0019 (10)−0.0086 (11)
N30.0203 (12)0.0307 (13)0.0196 (12)−0.0037 (10)−0.0018 (10)−0.0088 (10)
C10.0371 (18)0.0299 (17)0.0264 (16)−0.0033 (14)−0.0077 (14)−0.0094 (13)
C20.043 (2)0.0282 (16)0.0235 (16)−0.0093 (14)−0.0060 (14)−0.0045 (13)
C30.043 (2)0.0338 (17)0.0197 (15)−0.0132 (15)−0.0029 (14)−0.0100 (13)
C40.0326 (17)0.0341 (17)0.0258 (16)−0.0071 (14)−0.0014 (13)−0.0153 (14)
C50.0341 (17)0.0289 (16)0.0192 (14)−0.0075 (13)−0.0055 (12)−0.0107 (12)
C60.0307 (16)0.0304 (16)0.0188 (14)−0.0069 (13)−0.0023 (12)−0.0120 (12)
C70.0307 (17)0.0334 (17)0.0248 (16)−0.0082 (13)0.0006 (13)−0.0122 (13)
C80.0311 (17)0.0384 (18)0.0293 (16)−0.0005 (14)−0.0070 (13)−0.0200 (14)
C90.0348 (18)0.0301 (16)0.0271 (16)−0.0024 (14)−0.0057 (14)−0.0125 (13)
C100.0310 (17)0.0276 (16)0.0241 (15)−0.0063 (13)−0.0021 (13)−0.0099 (13)
C110.051 (2)0.0370 (19)0.0270 (17)−0.0181 (17)0.0017 (16)−0.0083 (15)
C120.0327 (19)0.048 (2)0.045 (2)0.0002 (16)−0.0086 (16)−0.0181 (18)
C130.0263 (16)0.0268 (15)0.0248 (15)−0.0061 (12)−0.0012 (12)−0.0076 (13)
C140.0266 (16)0.0314 (17)0.0303 (16)−0.0056 (13)−0.0029 (13)−0.0142 (14)
C150.0262 (16)0.0322 (17)0.0306 (17)0.0024 (13)−0.0085 (13)−0.0156 (14)
C160.0269 (16)0.0305 (16)0.0221 (15)0.0023 (13)−0.0050 (12)−0.0105 (13)
C170.0211 (15)0.0262 (15)0.0224 (15)0.0007 (12)−0.0041 (12)−0.0094 (12)
C180.0211 (14)0.0243 (15)0.0225 (14)0.0020 (11)−0.0043 (12)−0.0093 (12)
C190.0285 (16)0.0271 (15)0.0221 (15)−0.0012 (12)−0.0040 (12)−0.0077 (12)
C200.0245 (15)0.0247 (15)0.0284 (16)−0.0006 (12)0.0021 (13)−0.0078 (13)
C210.0254 (16)0.0291 (16)0.0347 (18)−0.0055 (13)−0.0035 (13)−0.0089 (14)
C220.0266 (16)0.0340 (17)0.0300 (17)−0.0069 (13)−0.0062 (13)−0.0135 (14)
C230.045 (2)0.043 (2)0.0341 (19)−0.0044 (16)−0.0155 (16)−0.0176 (16)
C240.041 (2)0.0316 (18)0.0310 (18)−0.0087 (15)0.0018 (15)−0.0037 (15)
Cl20.0400 (5)0.0330 (5)0.0766 (7)0.0011 (4)−0.0211 (5)−0.0208 (5)
O1S0.0405 (15)0.0630 (18)0.0399 (15)−0.0082 (13)−0.0101 (12)0.0009 (13)
O1W0.0354 (14)0.0557 (17)0.0618 (18)−0.0113 (12)−0.0108 (13)−0.0195 (14)
C1S0.055 (3)0.048 (2)0.048 (2)−0.004 (2)−0.022 (2)−0.0080 (19)
C2S0.058 (3)0.102 (4)0.040 (2)0.012 (3)−0.010 (2)−0.012 (3)
Geometric parameters (Å, º)
V1—O11.643 (2)C12—H12B0.9800
V1—N42.112 (3)C12—H12C0.9800
V1—N12.122 (3)C13—C141.377 (5)
V1—N32.126 (3)C13—H13A0.9500
V1—N22.278 (3)C14—C151.392 (5)
V1—Cl12.3259 (10)C14—H14A0.9500
N1—C11.349 (4)C15—C161.388 (5)
N1—C51.355 (4)C15—C231.508 (4)
N2—C101.343 (4)C16—C171.387 (4)
N2—C61.351 (4)C16—H16A0.9500
N4—C221.339 (4)C17—C181.474 (4)
N4—C181.362 (4)C18—C191.384 (4)
N3—C131.334 (4)C19—C201.387 (4)
N3—C171.360 (4)C19—H19A0.9500
C1—C21.381 (5)C20—C211.385 (5)
C1—H1B0.9500C20—C241.499 (4)
C2—C31.392 (5)C21—C221.384 (5)
C2—H2A0.9500C21—H21A0.9500
C3—C41.393 (5)C22—H22A0.9500
C3—C111.509 (4)C23—H23A0.9800
C4—C51.385 (4)C23—H23B0.9800
C4—H4A0.9500C23—H23C0.9800
C5—C61.480 (4)C24—H24A0.9800
C6—C71.392 (5)C24—H24B0.9800
C7—C81.384 (5)C24—H24C0.9800
C7—H7A0.9500O1S—C1S1.408 (5)
C8—C91.388 (5)O1S—H1S0.9310
C8—C121.508 (5)O1W—H1W0.8444
C9—C101.382 (5)O1W—H2W0.9188
C9—H9A0.9500C1S—C2S1.493 (6)
C10—H10A0.9500C1S—H1SA0.9900
C11—H11A0.9800C1S—H1SB0.9900
C11—H11B0.9800C2S—H2SA0.9800
C11—H11C0.9800C2S—H2SB0.9800
C12—H12A0.9800C2S—H2SC0.9800
O1—V1—N4102.71 (10)C8—C12—H12A109.5
O1—V1—N194.54 (11)C8—C12—H12B109.5
N4—V1—N1160.77 (11)H12A—C12—H12B109.5
O1—V1—N394.03 (11)C8—C12—H12C109.5
N4—V1—N377.27 (10)H12A—C12—H12C109.5
N1—V1—N393.27 (10)H12B—C12—H12C109.5
O1—V1—N2165.96 (10)N3—C13—C14122.8 (3)
N4—V1—N288.49 (10)N3—C13—H13A118.6
N1—V1—N273.27 (10)C14—C13—H13A118.6
N3—V1—N280.04 (9)C13—C14—C15119.8 (3)
O1—V1—Cl198.86 (8)C13—C14—H14A120.1
N4—V1—Cl192.74 (8)C15—C14—H14A120.1
N1—V1—Cl192.94 (7)C16—C15—C14117.4 (3)
N3—V1—Cl1165.19 (8)C16—C15—C23121.8 (3)
N2—V1—Cl188.91 (7)C14—C15—C23120.8 (3)
C1—N1—C5118.0 (3)C17—C16—C15120.3 (3)
C1—N1—V1121.3 (2)C17—C16—H16A119.8
C5—N1—V1120.6 (2)C15—C16—H16A119.8
C10—N2—C6117.4 (3)N3—C17—C16121.2 (3)
C10—N2—V1126.8 (2)N3—C17—C18115.4 (3)
C6—N2—V1115.8 (2)C16—C17—C18123.4 (3)
C22—N4—C18118.1 (3)N4—C18—C19121.2 (3)
C22—N4—V1125.9 (2)N4—C18—C17115.5 (3)
C18—N4—V1115.9 (2)C19—C18—C17123.3 (3)
C13—N3—C17118.5 (3)C18—C19—C20120.5 (3)
C13—N3—V1125.8 (2)C18—C19—H19A119.8
C17—N3—V1115.40 (19)C20—C19—H19A119.8
N1—C1—C2123.4 (3)C21—C20—C19117.9 (3)
N1—C1—H1B118.3C21—C20—C24122.0 (3)
C2—C1—H1B118.3C19—C20—C24120.1 (3)
C1—C2—C3118.8 (3)C22—C21—C20119.3 (3)
C1—C2—H2A120.6C22—C21—H21A120.4
C3—C2—H2A120.6C20—C21—H21A120.4
C2—C3—C4117.9 (3)N4—C22—C21123.0 (3)
C2—C3—C11121.2 (3)N4—C22—H22A118.5
C4—C3—C11121.0 (3)C21—C22—H22A118.5
C5—C4—C3120.5 (3)C15—C23—H23A109.5
C5—C4—H4A119.7C15—C23—H23B109.5
C3—C4—H4A119.7H23A—C23—H23B109.5
N1—C5—C4121.3 (3)C15—C23—H23C109.5
N1—C5—C6115.5 (3)H23A—C23—H23C109.5
C4—C5—C6123.2 (3)H23B—C23—H23C109.5
N2—C6—C7122.1 (3)C20—C24—H24A109.5
N2—C6—C5114.7 (3)C20—C24—H24B109.5
C7—C6—C5123.2 (3)H24A—C24—H24B109.5
C8—C7—C6120.1 (3)C20—C24—H24C109.5
C8—C7—H7A119.9H24A—C24—H24C109.5
C6—C7—H7A119.9H24B—C24—H24C109.5
C7—C8—C9117.6 (3)C1S—O1S—H1S99.6
C7—C8—C12121.7 (3)H1W—O1W—H2W130.3
C9—C8—C12120.8 (3)O1S—C1S—C2S112.2 (4)
C10—C9—C8119.4 (3)O1S—C1S—H1SA109.2
C10—C9—H9A120.3C2S—C1S—H1SA109.2
C8—C9—H9A120.3O1S—C1S—H1SB109.2
N2—C10—C9123.4 (3)C2S—C1S—H1SB109.2
N2—C10—H10A118.3H1SA—C1S—H1SB107.9
C9—C10—H10A118.3C1S—C2S—H2SA109.5
C3—C11—H11A109.5C1S—C2S—H2SB109.5
C3—C11—H11B109.5H2SA—C2S—H2SB109.5
H11A—C11—H11B109.5C1S—C2S—H2SC109.5
C3—C11—H11C109.5H2SA—C2S—H2SC109.5
H11A—C11—H11C109.5H2SB—C2S—H2SC109.5
H11B—C11—H11C109.5
O1—V1—N1—C1−8.2 (3)V1—N1—C5—C6−2.2 (3)
N4—V1—N1—C1−162.1 (3)C3—C4—C5—N11.1 (5)
N3—V1—N1—C1−102.5 (2)C3—C4—C5—C6−178.7 (3)
N2—V1—N1—C1178.9 (3)C10—N2—C6—C7−0.9 (4)
Cl1—V1—N1—C191.0 (2)V1—N2—C6—C7175.3 (2)
O1—V1—N1—C5173.1 (2)C10—N2—C6—C5−180.0 (3)
N4—V1—N1—C519.2 (4)V1—N2—C6—C5−3.8 (3)
N3—V1—N1—C578.8 (2)N1—C5—C6—N24.0 (4)
N2—V1—N1—C50.2 (2)C4—C5—C6—N2−176.2 (3)
Cl1—V1—N1—C5−87.8 (2)N1—C5—C6—C7−175.2 (3)
O1—V1—N2—C10147.3 (4)C4—C5—C6—C74.7 (5)
N4—V1—N2—C104.0 (3)N2—C6—C7—C80.5 (5)
N1—V1—N2—C10177.8 (3)C5—C6—C7—C8179.6 (3)
N3—V1—N2—C1081.3 (3)C6—C7—C8—C90.0 (5)
Cl1—V1—N2—C10−88.8 (2)C6—C7—C8—C12−179.9 (3)
O1—V1—N2—C6−28.5 (5)C7—C8—C9—C10−0.1 (5)
N4—V1—N2—C6−171.8 (2)C12—C8—C9—C10179.8 (3)
N1—V1—N2—C62.1 (2)C6—N2—C10—C90.7 (4)
N3—V1—N2—C6−94.4 (2)V1—N2—C10—C9−175.0 (2)
Cl1—V1—N2—C695.5 (2)C8—C9—C10—N2−0.3 (5)
O1—V1—N4—C2290.6 (3)C17—N3—C13—C14−2.0 (5)
N1—V1—N4—C22−116.2 (3)V1—N3—C13—C14171.4 (2)
N3—V1—N4—C22−178.1 (3)N3—C13—C14—C150.0 (5)
N2—V1—N4—C22−98.0 (3)C13—C14—C15—C162.2 (5)
Cl1—V1—N4—C22−9.1 (3)C13—C14—C15—C23−177.7 (3)
O1—V1—N4—C18−86.5 (2)C14—C15—C16—C17−2.3 (5)
N1—V1—N4—C1866.7 (4)C23—C15—C16—C17177.6 (3)
N3—V1—N4—C184.8 (2)C13—N3—C17—C161.8 (4)
N2—V1—N4—C1884.9 (2)V1—N3—C17—C16−172.3 (2)
Cl1—V1—N4—C18173.8 (2)C13—N3—C17—C18−178.8 (3)
O1—V1—N3—C13−77.9 (3)V1—N3—C17—C187.1 (3)
N4—V1—N3—C13180.0 (3)C15—C16—C17—N30.4 (5)
N1—V1—N3—C1316.9 (3)C15—C16—C17—C18−179.0 (3)
N2—V1—N3—C1389.3 (3)C22—N4—C18—C191.1 (4)
Cl1—V1—N3—C13131.5 (3)V1—N4—C18—C19178.4 (2)
O1—V1—N3—C1795.7 (2)C22—N4—C18—C17−179.9 (3)
N4—V1—N3—C17−6.5 (2)V1—N4—C18—C17−2.6 (3)
N1—V1—N3—C17−169.5 (2)N3—C17—C18—N4−3.0 (4)
N2—V1—N3—C17−97.2 (2)C16—C17—C18—N4176.4 (3)
Cl1—V1—N3—C17−54.9 (4)N3—C17—C18—C19175.9 (3)
C5—N1—C1—C2−0.4 (5)C16—C17—C18—C19−4.7 (5)
V1—N1—C1—C2−179.1 (2)N4—C18—C19—C20−1.1 (5)
N1—C1—C2—C31.2 (5)C17—C18—C19—C20−179.9 (3)
C1—C2—C3—C4−0.9 (5)C18—C19—C20—C210.3 (5)
C1—C2—C3—C11179.9 (3)C18—C19—C20—C24179.7 (3)
C2—C3—C4—C5−0.3 (5)C19—C20—C21—C220.4 (5)
C11—C3—C4—C5178.9 (3)C24—C20—C21—C22−179.1 (3)
C1—N1—C5—C4−0.8 (4)C18—N4—C22—C21−0.4 (5)
V1—N1—C5—C4177.9 (2)V1—N4—C22—C21−177.5 (2)
C1—N1—C5—C6179.0 (3)C20—C21—C22—N4−0.3 (5)
Hydrogen-bond geometry (Å, º)
D—H···AD—HH···AD···AD—H···A
O1S—H1S···Cl20.932.243.128 (3)159
O1W—H1W···Cl2i0.842.453.221 (3)152
O1W—H2W···Cl2ii0.922.373.284 (3)171
C1—H1B···O10.952.512.999 (4)112
C2—H2A···O1Siii0.952.413.301 (4)155
C4—H4A···Cl1iv0.952.763.670 (4)160
C7—H7A···Cl1iv0.952.773.626 (3)151
C9—H9A···Cl2ii0.952.633.561 (4)165
C13—H13A···O1Siv0.952.593.284 (4)130
C14—H14A···Cl2iv0.952.623.558 (3)170
C19—H19A···O1v0.952.523.229 (4)132
C21—H21A···O1Wvi0.952.453.315 (5)151
C22—H22A···Cl10.952.643.262 (3)123
Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y, −z+1; (iii) x, y+1, z; (iv) −x+1, −y+1, −z+1; (v) −x, −y+1, −z+2; (vi) −x, −y, −z+2.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2588).
  • Ahmadi, R., Kalateh, K., Abedi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1306–m1307. [PMC free article] [PubMed]
  • Alizadeh, R., Mohammadi Eshlaghi, P. & Amani, V. (2010). Acta Cryst. E66, m996. [PMC free article] [PubMed]
  • Amani, V., Safari, N., Notash, B. & Khavasi, H. R. (2009). J. Coord. Chem. 62, 1939–1950.
  • Bruker (2007). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Hojjat Kashani, L., Amani, V., Yousefi, M. & Khavasi, H. R. (2008). Acta Cryst. E64, m905–m906. [PMC free article] [PubMed]
  • Kalateh, K., Ahmadi, R. & Amani, V. (2010). Acta Cryst. E66, m512. [PMC free article] [PubMed]
  • Kalateh, K., Ebadi, A., Ahmadi, R., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1397–m1398. [PMC free article] [PubMed]
  • Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Shirvan, S. A. & Haydari Dezfuli, S. (2011). Acta Cryst. E67, m1866–m1867. [PMC free article] [PubMed]
  • Shirvan, S. A. & Haydari Dezfuli, S. (2012a). Acta Cryst. E68, m1006–m1007. [PMC free article] [PubMed]
  • Shirvan, S. A. & Haydari Dezfuli, S. (2012b). Acta Cryst. E68, m1189–m1190. [PMC free article] [PubMed]
  • Triantafillou, G. D., Tolis, E. I., Terzis, A., Deligiannakis, Y., Raptopoulou, C. P., Sigalas, M. P. & Kabanos, T. A. (2004). Inorg. Chem. 43, 79–91. [PubMed]
  • Yousefi, M., Tadayon Pour, N., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1259. [PMC free article] [PubMed]
Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of
International Union of Crystallography