metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Di­chlorido(4′-ferrocenyl-2,2′:6′,2′′-terpyridine-κ3N,N′,N′′)zinc aceto­nitrile monosolvate

aKey Laboratory of Functional Organometallic Materials, Department of Chemistry and Material Science, Hengyang Normal University, Hengyang, Hunan 421008, People's Republic of China
*Correspondence e-mail: sptang88@163.com

(Received 21 June 2011; accepted 25 June 2011; online 2 July 2011)

The title complex, [FeZn(C5H5)Cl2(C20H14N3)]·CH3CN, is composed of one ZnII atom, one 4′-ferrocenyl-2,2′:6′,2′′-terpyridine (fctpy) ligand, two Cl atoms and one acetonitrile solvent mol­ecule. The ZnII atom is five-coordinated in a trigonal–bipyramidal geometry by the tridentate chelating fctpy ligand and two Cl atoms.

Related literature

For 4′-ferrocenyl-2,2′:6′,2"-terpyridine metal complexes, see: Aguado et al. (2005[Aguado, J. E., Calhorda, M. J., Gimeno, M. C. & Laguna, A. (2005). Chem. Commun. pp. 3355-3356.]); Constable et al. (1994[Constable, E. C., Edwards, A. J., Martinez-Manez, R., Raithby, P. R. & Thompson, A. M. W. C. (1994). J. Chem. Soc. Dalton Trans. pp. 645-650.]); Farlow et al. (1993[Farlow, B., Nile, T. A. & Walsh, J. L. (1993). Polyhedron, 12, 2891-2894.]); Tang & Kuang (2007[Tang, S.-P. & Kuang, D.-Z. (2007). Acta Cryst. E63, m3007.]); Tang et al. (2009[Tang, S.-P., Kuang, D.-Z. & Feng, Y.-L. (2009). Acta Cryst. E65, m830.]).

[Scheme 1]

Experimental

Crystal data
  • [FeZn(C5H5)Cl2(C20H14N3)]·C2H3N

  • Mr = 594.61

  • Monoclinic, P 21 /c

  • a = 13.799 (2) Å

  • b = 12.998 (2) Å

  • c = 14.594 (2) Å

  • β = 104.514 (4)°

  • V = 2534.0 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.75 mm−1

  • T = 295 K

  • 0.18 × 0.14 × 0.10 mm

Data collection
  • Bruker APEX area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.743, Tmax = 0.844

  • 12737 measured reflections

  • 4938 independent reflections

  • 3301 reflections with I > 2σ(I)

  • Rint = 0.051

Refinement
  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.131

  • S = 1.02

  • 4938 reflections

  • 317 parameters

  • H-atom parameters constrained

  • Δρmax = 0.77 e Å−3

  • Δρmin = −0.40 e Å−3

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

4'-Ferrocenyl-2,2':6',2"-terpyridine (fctpy) has rencently been paid more attentions for its good chelating abilities towards transition metal ions, such as AuI, RuII, CoII, FeII, CuII, and ZnIIcomplexes (Aguado et al., 2005; Constable et al., 1994; Farlow et al., 1993; Tang & Kuang, 2007; Tang & Kuang et al., 2009).some of its complexes exhibited interesting electrochemical and luminescent properties. In this work, a new ZnII complex of fctpy is here reported.

In the title complex, the ZnII atom is five-coordinated by three N atoms from fctpy ligand and two Cl atoms, displaying a trigonal bipyramidal geometry with two N atoms of outer pyridine rings of fctpy ligand located at apical sites. The Zn—N and Zn—Cl bond lengths are in the range of 2.093 (3)—2.210 (4) and 2.2490 (13)—2.2672 (14) Å, respectively. The angles subtended by the terpyridyl ligand are 74.85 (13) and 74.46 (14) °.

Related literature top

For 4'-ferrocenyl-2,2':6',2"-terpyridine metal complexes, see: Aguado et al. (2005); Constable et al. (1994); Farlow et al. (1993); Tang & Kuang (2007); Tang & Kuang et al. (2009).

Experimental top

The ligand fctpy was synthesized according to the reported procedure (Farlow et al., 1993). A solution of zinc chloride (6.8 mg, 0.05 mmol) and fctpy (21.0 mg, 0.05 mmol) in methanol (10 ml) was stirred for 4 h. The product was filtered off and dried. The product was filtered off and dried. The precipitate were recrystallized from acetonitrile (5 ml) to give red prism-shaped crystals of the title complex after one week. Yield: 16 mg (53.9%).

Refinement top

All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.93 Å, Uiso=1.2Ueq (C) for aromatic; 0.98 Å, Uiso= 1.2Ueq (C) for cyclopentadiene; 0.96 Å, Uiso= 1.5Ueq (C) for CH3 atoms.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title complex, with displacement ellipsoids drawn at the 30% probability level, and H atoms as spheres of arbitrary radius.
Dichlorido(4'-ferrocenyl-2,2':6',2''-terpyridine- κ3N,N',N'')zinc acetonitrile monosolvate top
Crystal data top
[FeZn(C5H5)Cl2(C20H14N3)]·C2H3NF(000) = 1208
Mr = 594.61Dx = 1.559 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1833 reflections
a = 13.799 (2) Åθ = 2.4–21.3°
b = 12.998 (2) ŵ = 1.75 mm1
c = 14.594 (2) ÅT = 295 K
β = 104.514 (4)°Prism, red
V = 2534.0 (6) Å30.18 × 0.14 × 0.10 mm
Z = 4
Data collection top
Bruker APEX area-detector
diffractometer
4938 independent reflections
Radiation source: fine-focus sealed tube3301 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
ϕ and ω scansθmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1715
Tmin = 0.743, Tmax = 0.844k = 1416
12737 measured reflectionsl = 1318
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0571P)2]
where P = (Fo2 + 2Fc2)/3
4938 reflections(Δ/σ)max < 0.001
317 parametersΔρmax = 0.77 e Å3
0 restraintsΔρmin = 0.40 e Å3
Crystal data top
[FeZn(C5H5)Cl2(C20H14N3)]·C2H3NV = 2534.0 (6) Å3
Mr = 594.61Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.799 (2) ŵ = 1.75 mm1
b = 12.998 (2) ÅT = 295 K
c = 14.594 (2) Å0.18 × 0.14 × 0.10 mm
β = 104.514 (4)°
Data collection top
Bruker APEX area-detector
diffractometer
4938 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3301 reflections with I > 2σ(I)
Tmin = 0.743, Tmax = 0.844Rint = 0.051
12737 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.131H-atom parameters constrained
S = 1.02Δρmax = 0.77 e Å3
4938 reflectionsΔρmin = 0.40 e Å3
317 parameters
Special details top

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) top
xyzUiso*/Ueq
Fe20.15322 (5)0.18976 (5)0.06212 (4)0.0384 (2)
Zn10.27254 (4)0.38084 (4)0.02199 (4)0.04109 (18)
Cl30.15301 (10)0.44465 (10)0.10085 (9)0.0582 (4)
Cl40.39084 (10)0.49174 (10)0.09763 (10)0.0595 (4)
N10.1865 (3)0.3817 (3)0.1303 (3)0.0410 (9)
N20.2663 (3)0.2268 (3)0.0618 (3)0.0353 (9)
N30.3560 (3)0.2940 (3)0.0636 (3)0.0408 (9)
N40.4086 (5)0.6416 (5)0.4004 (5)0.116 (2)
C10.1444 (4)0.4648 (4)0.1587 (4)0.0522 (13)
H10.14970.52760.12980.063*
C20.0938 (4)0.4612 (4)0.2286 (4)0.0572 (14)
H20.06480.52000.24660.069*
C30.0872 (4)0.3681 (4)0.2710 (4)0.0558 (14)
H30.05360.36370.31870.067*
C40.1298 (4)0.2809 (4)0.2437 (3)0.0476 (12)
H40.12620.21790.27280.057*
C50.1783 (3)0.2902 (3)0.1714 (3)0.0356 (10)
C60.2218 (3)0.2022 (3)0.1314 (3)0.0347 (10)
C70.2165 (3)0.1017 (3)0.1600 (3)0.0366 (10)
H70.18690.08630.20900.044*
C80.2560 (3)0.0232 (3)0.1149 (3)0.0370 (10)
C90.3017 (3)0.0500 (3)0.0432 (3)0.0421 (11)
H90.32960.00040.01250.050*
C100.3053 (3)0.1532 (3)0.0181 (3)0.0361 (10)
C110.3525 (3)0.1907 (3)0.0571 (3)0.0375 (11)
C120.3885 (4)0.1273 (4)0.1163 (3)0.0476 (12)
H120.38400.05620.11160.057*
C130.4318 (4)0.1714 (4)0.1834 (3)0.0499 (13)
H130.45640.12990.22430.060*
C140.4378 (4)0.2756 (4)0.1888 (3)0.0507 (13)
H140.46760.30660.23230.061*
C150.3984 (4)0.3343 (4)0.1278 (3)0.0495 (13)
H150.40160.40560.13180.059*
C160.2486 (3)0.0851 (3)0.1418 (3)0.0370 (11)
C170.1829 (4)0.1262 (3)0.1942 (3)0.0435 (12)
H170.13580.08680.22080.052*
C180.1969 (4)0.2339 (4)0.1999 (3)0.0539 (14)
H180.16040.28180.23100.065*
C190.2716 (4)0.2618 (4)0.1534 (4)0.0510 (13)
H190.29590.33150.14670.061*
C200.3029 (4)0.1705 (3)0.1163 (3)0.0462 (12)
H200.35320.16610.07950.055*
C210.0683 (5)0.1180 (5)0.0538 (4)0.0713 (15)
H210.06890.04390.06640.086*
C220.0069 (5)0.1663 (5)0.0061 (4)0.0748 (15)
H220.04390.13340.02030.090*
C230.0298 (5)0.2713 (5)0.0031 (5)0.0820 (16)
H230.00240.32590.02500.098*
C240.1066 (5)0.2835 (5)0.0504 (4)0.0818 (17)
H240.13780.34870.06100.098*
C250.1287 (5)0.1888 (5)0.0803 (4)0.0752 (15)
H250.17900.17440.11560.090*
C260.4023 (5)0.7265 (5)0.4002 (4)0.0667 (16)
C270.3915 (5)0.8365 (5)0.3999 (5)0.089 (2)
H27A0.35980.85940.33700.133*
H27B0.45630.86780.42060.133*
H27C0.35110.85560.44210.133*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe20.0469 (4)0.0330 (4)0.0339 (4)0.0007 (3)0.0076 (3)0.0003 (3)
Zn10.0501 (4)0.0310 (3)0.0439 (3)0.0017 (2)0.0149 (3)0.0001 (2)
Cl30.0724 (9)0.0544 (8)0.0457 (8)0.0163 (7)0.0108 (6)0.0017 (6)
Cl40.0604 (9)0.0472 (7)0.0716 (9)0.0133 (6)0.0179 (7)0.0126 (7)
N10.050 (2)0.029 (2)0.047 (2)0.0023 (17)0.0170 (19)0.0052 (18)
N20.035 (2)0.0300 (19)0.042 (2)0.0019 (16)0.0121 (17)0.0020 (17)
N30.046 (2)0.041 (2)0.039 (2)0.0018 (18)0.0165 (18)0.0009 (18)
N40.154 (7)0.072 (4)0.113 (6)0.000 (4)0.018 (5)0.012 (4)
C10.069 (4)0.033 (3)0.056 (3)0.004 (2)0.018 (3)0.004 (2)
C20.067 (4)0.050 (3)0.059 (4)0.012 (3)0.025 (3)0.010 (3)
C30.064 (4)0.061 (3)0.051 (3)0.010 (3)0.031 (3)0.003 (3)
C40.062 (3)0.042 (3)0.043 (3)0.001 (2)0.020 (3)0.002 (2)
C50.037 (3)0.035 (2)0.034 (3)0.0047 (19)0.008 (2)0.003 (2)
C60.034 (3)0.032 (2)0.038 (3)0.0028 (19)0.010 (2)0.000 (2)
C70.038 (3)0.037 (3)0.034 (2)0.001 (2)0.008 (2)0.002 (2)
C80.036 (3)0.036 (2)0.037 (3)0.006 (2)0.005 (2)0.001 (2)
C90.051 (3)0.034 (2)0.042 (3)0.004 (2)0.015 (2)0.003 (2)
C100.034 (3)0.036 (2)0.039 (3)0.000 (2)0.010 (2)0.001 (2)
C110.040 (3)0.035 (3)0.038 (3)0.001 (2)0.011 (2)0.002 (2)
C120.055 (3)0.046 (3)0.046 (3)0.001 (2)0.019 (2)0.007 (2)
C130.050 (3)0.057 (3)0.048 (3)0.007 (2)0.021 (2)0.006 (3)
C140.053 (3)0.067 (4)0.038 (3)0.005 (3)0.022 (2)0.004 (3)
C150.051 (3)0.048 (3)0.051 (3)0.002 (2)0.015 (3)0.003 (3)
C160.046 (3)0.027 (2)0.035 (3)0.0047 (19)0.006 (2)0.0026 (19)
C170.057 (3)0.040 (3)0.033 (3)0.008 (2)0.011 (2)0.002 (2)
C180.079 (4)0.038 (3)0.041 (3)0.011 (3)0.009 (3)0.007 (2)
C190.058 (3)0.030 (3)0.058 (3)0.005 (2)0.001 (3)0.001 (2)
C200.047 (3)0.035 (3)0.055 (3)0.001 (2)0.010 (2)0.002 (2)
C210.082 (3)0.071 (3)0.048 (3)0.004 (3)0.008 (2)0.006 (3)
C220.061 (3)0.097 (3)0.057 (3)0.008 (3)0.004 (2)0.008 (3)
C230.076 (3)0.086 (3)0.065 (3)0.030 (3)0.018 (3)0.007 (3)
C240.088 (3)0.073 (3)0.061 (3)0.017 (3)0.025 (3)0.033 (3)
C250.079 (3)0.094 (3)0.045 (3)0.003 (3)0.001 (2)0.012 (3)
C260.077 (4)0.073 (4)0.049 (4)0.007 (3)0.014 (3)0.005 (3)
C270.100 (5)0.073 (5)0.083 (5)0.015 (4)0.003 (4)0.007 (4)
Geometric parameters (Å, º) top
Fe2—C242.017 (5)C8—C161.471 (6)
Fe2—C252.020 (6)C9—C101.394 (6)
Fe2—C212.028 (5)C9—H90.9300
Fe2—C232.029 (5)C10—C111.491 (6)
Fe2—C182.031 (5)C11—C121.374 (6)
Fe2—C202.034 (5)C12—C131.393 (6)
Fe2—C222.038 (6)C12—H120.9300
Fe2—C162.041 (4)C13—C141.361 (7)
Fe2—C172.042 (5)C13—H130.9300
Fe2—C192.056 (5)C14—C151.384 (7)
Zn1—N22.093 (3)C14—H140.9300
Zn1—N12.202 (4)C15—H150.9300
Zn1—N32.210 (4)C16—C171.429 (6)
Zn1—Cl42.2490 (13)C16—C201.439 (6)
Zn1—Cl32.2672 (14)C17—C181.412 (6)
N1—C11.340 (6)C17—H170.9800
N1—C51.350 (5)C18—C191.416 (7)
N2—C101.335 (5)C18—H180.9800
N2—C61.350 (5)C19—C201.416 (6)
N3—C151.329 (6)C19—H190.9800
N3—C111.348 (5)C20—H200.9800
N4—C261.107 (8)C21—C251.361 (8)
C1—C21.374 (7)C21—C221.376 (8)
C1—H10.9300C21—H210.9800
C2—C31.372 (7)C22—C231.399 (8)
C2—H20.9300C22—H220.9800
C3—C41.381 (6)C23—C241.412 (9)
C3—H30.9300C23—H230.9800
C4—C51.389 (6)C24—C251.366 (8)
C4—H40.9300C24—H240.9800
C5—C61.479 (6)C25—H250.9800
C6—C71.379 (6)C26—C271.437 (8)
C7—C81.397 (6)C27—H27A0.9600
C7—H70.9300C27—H27B0.9600
C8—C91.396 (6)C27—H27C0.9600
C24—Fe2—C2539.5 (2)C10—C9—C8119.3 (4)
C24—Fe2—C2166.3 (2)C10—C9—H9120.3
C25—Fe2—C2139.3 (2)C8—C9—H9120.3
C24—Fe2—C2340.9 (3)N2—C10—C9121.3 (4)
C25—Fe2—C2367.5 (3)N2—C10—C11114.8 (4)
C21—Fe2—C2366.9 (3)C9—C10—C11123.9 (4)
C24—Fe2—C18126.2 (2)N3—C11—C12121.9 (4)
C25—Fe2—C18162.1 (2)N3—C11—C10114.1 (4)
C21—Fe2—C18157.2 (3)C12—C11—C10124.0 (4)
C23—Fe2—C18108.8 (2)C11—C12—C13118.8 (5)
C24—Fe2—C20118.5 (2)C11—C12—H12120.6
C25—Fe2—C20106.9 (2)C13—C12—H12120.6
C21—Fe2—C20125.9 (2)C14—C13—C12119.6 (5)
C23—Fe2—C20153.9 (2)C14—C13—H13120.2
C18—Fe2—C2068.3 (2)C12—C13—H13120.2
C24—Fe2—C2267.5 (3)C13—C14—C15118.1 (5)
C25—Fe2—C2266.8 (3)C13—C14—H14120.9
C21—Fe2—C2239.6 (2)C15—C14—H14120.9
C23—Fe2—C2240.2 (2)N3—C15—C14123.3 (5)
C18—Fe2—C22122.5 (3)N3—C15—H15118.3
C20—Fe2—C22163.1 (2)C14—C15—H15118.3
C24—Fe2—C16153.5 (3)C17—C16—C20106.9 (4)
C25—Fe2—C16120.0 (2)C17—C16—C8126.6 (4)
C21—Fe2—C16108.9 (2)C20—C16—C8126.4 (4)
C23—Fe2—C16163.9 (3)C17—C16—Fe269.6 (2)
C18—Fe2—C1668.64 (18)C20—C16—Fe269.0 (2)
C20—Fe2—C1641.35 (17)C8—C16—Fe2124.3 (3)
C22—Fe2—C16126.7 (2)C18—C17—C16107.8 (4)
C24—Fe2—C17163.9 (3)C18—C17—Fe269.3 (3)
C25—Fe2—C17155.6 (2)C16—C17—Fe269.5 (3)
C21—Fe2—C17122.6 (2)C18—C17—H17126.1
C23—Fe2—C17126.9 (3)C16—C17—H17126.1
C18—Fe2—C1740.57 (18)Fe2—C17—H17126.1
C20—Fe2—C1768.8 (2)C17—C18—C19109.3 (4)
C22—Fe2—C17109.9 (2)C17—C18—Fe270.1 (3)
C16—Fe2—C1740.96 (17)C19—C18—Fe270.7 (3)
C24—Fe2—C19107.0 (2)C17—C18—H18125.3
C25—Fe2—C19124.8 (2)C19—C18—H18125.3
C21—Fe2—C19161.6 (3)Fe2—C18—H18125.3
C23—Fe2—C19120.2 (2)C18—C19—C20107.3 (4)
C18—Fe2—C1940.5 (2)C18—C19—Fe268.8 (3)
C20—Fe2—C1940.51 (18)C20—C19—Fe268.9 (3)
C22—Fe2—C19156.0 (2)C18—C19—H19126.4
C16—Fe2—C1968.93 (18)C20—C19—H19126.4
C17—Fe2—C1968.5 (2)Fe2—C19—H19126.4
N2—Zn1—N174.85 (13)C19—C20—C16108.6 (4)
N2—Zn1—N374.46 (14)C19—C20—Fe270.6 (3)
N1—Zn1—N3149.31 (13)C16—C20—Fe269.6 (3)
N2—Zn1—Cl4123.51 (10)C19—C20—H20125.7
N1—Zn1—Cl495.74 (10)C16—C20—H20125.7
N3—Zn1—Cl4100.82 (10)Fe2—C20—H20125.7
N2—Zn1—Cl3119.82 (10)C25—C21—C22109.4 (6)
N1—Zn1—Cl398.58 (11)C25—C21—Fe270.0 (4)
N3—Zn1—Cl396.82 (10)C22—C21—Fe270.6 (3)
Cl4—Zn1—Cl3116.64 (5)C25—C21—H21125.3
C1—N1—C5118.8 (4)C22—C21—H21125.3
C1—N1—Zn1125.4 (3)Fe2—C21—H21125.3
C5—N1—Zn1115.7 (3)C21—C22—C23107.4 (6)
C10—N2—C6120.2 (4)C21—C22—Fe269.8 (3)
C10—N2—Zn1120.2 (3)C23—C22—Fe269.6 (3)
C6—N2—Zn1119.6 (3)C21—C22—H22126.3
C15—N3—C11118.2 (4)C23—C22—H22126.3
C15—N3—Zn1125.5 (3)Fe2—C22—H22126.3
C11—N3—Zn1115.8 (3)C22—C23—C24106.5 (6)
N1—C1—C2122.8 (5)C22—C23—Fe270.2 (3)
N1—C1—H1118.6C24—C23—Fe269.1 (3)
C2—C1—H1118.6C22—C23—H23126.7
C3—C2—C1117.9 (5)C24—C23—H23126.7
C3—C2—H2121.0Fe2—C23—H23126.7
C1—C2—H2121.0C25—C24—C23108.1 (6)
C2—C3—C4120.8 (5)C25—C24—Fe270.4 (3)
C2—C3—H3119.6C23—C24—Fe270.1 (3)
C4—C3—H3119.6C25—C24—H24126.0
C3—C4—C5118.0 (5)C23—C24—H24126.0
C3—C4—H4121.0Fe2—C24—H24126.0
C5—C4—H4121.0C21—C25—C24108.5 (6)
N1—C5—C4121.6 (4)C21—C25—Fe270.7 (4)
N1—C5—C6114.8 (4)C24—C25—Fe270.1 (4)
C4—C5—C6123.6 (4)C21—C25—H25125.7
N2—C6—C7121.4 (4)C24—C25—H25125.7
N2—C6—C5114.8 (4)Fe2—C25—H25125.7
C7—C6—C5123.8 (4)N4—C26—C27178.5 (8)
C6—C7—C8119.5 (4)C26—C27—H27A109.5
C6—C7—H7120.2C26—C27—H27B109.5
C8—C7—H7120.2H27A—C27—H27B109.5
C9—C8—C7118.2 (4)C26—C27—H27C109.5
C9—C8—C16120.9 (4)H27A—C27—H27C109.5
C7—C8—C16120.8 (4)H27B—C27—H27C109.5
N2—Zn1—N1—C1177.1 (4)C17—Fe2—C18—C19120.0 (4)
N3—Zn1—N1—C1177.7 (3)C17—C18—C19—C201.4 (6)
Cl4—Zn1—N1—C159.7 (4)Fe2—C18—C19—C2058.3 (3)
Cl3—Zn1—N1—C158.4 (4)C17—C18—C19—Fe259.7 (3)
N2—Zn1—N1—C54.2 (3)C24—Fe2—C19—C18126.3 (4)
N3—Zn1—N1—C53.6 (5)C25—Fe2—C19—C18166.0 (3)
Cl4—Zn1—N1—C5119.0 (3)C21—Fe2—C19—C18167.9 (6)
Cl3—Zn1—N1—C5122.9 (3)C23—Fe2—C19—C1883.8 (4)
N1—Zn1—N2—C10176.3 (3)C20—Fe2—C19—C18119.4 (4)
N3—Zn1—N2—C104.1 (3)C22—Fe2—C19—C1853.6 (7)
Cl4—Zn1—N2—C1096.9 (3)C16—Fe2—C19—C1881.4 (3)
Cl3—Zn1—N2—C1085.0 (3)C17—Fe2—C19—C1837.3 (3)
N1—Zn1—N2—C63.1 (3)C24—Fe2—C19—C20114.2 (4)
N3—Zn1—N2—C6176.6 (3)C25—Fe2—C19—C2074.5 (4)
Cl4—Zn1—N2—C683.8 (3)C21—Fe2—C19—C2048.5 (8)
Cl3—Zn1—N2—C694.4 (3)C23—Fe2—C19—C20156.7 (4)
N2—Zn1—N3—C15178.7 (4)C18—Fe2—C19—C20119.4 (4)
N1—Zn1—N3—C15179.3 (3)C22—Fe2—C19—C20173.1 (5)
Cl4—Zn1—N3—C1559.3 (4)C16—Fe2—C19—C2038.1 (3)
Cl3—Zn1—N3—C1559.6 (4)C17—Fe2—C19—C2082.2 (3)
N2—Zn1—N3—C117.0 (3)C18—C19—C20—C161.2 (6)
N1—Zn1—N3—C117.6 (5)Fe2—C19—C20—C1659.4 (3)
Cl4—Zn1—N3—C11129.0 (3)C18—C19—C20—Fe258.3 (3)
Cl3—Zn1—N3—C11112.1 (3)C17—C16—C20—C190.6 (5)
C5—N1—C1—C20.5 (7)C8—C16—C20—C19177.9 (4)
Zn1—N1—C1—C2178.2 (4)Fe2—C16—C20—C1960.1 (3)
N1—C1—C2—C30.5 (8)C17—C16—C20—Fe259.5 (3)
C1—C2—C3—C40.3 (8)C8—C16—C20—Fe2117.9 (4)
C2—C3—C4—C50.8 (8)C24—Fe2—C20—C1982.9 (4)
C1—N1—C5—C41.7 (7)C25—Fe2—C20—C19124.2 (3)
Zn1—N1—C5—C4177.1 (3)C21—Fe2—C20—C19163.1 (3)
C1—N1—C5—C6176.5 (4)C23—Fe2—C20—C1951.0 (7)
Zn1—N1—C5—C64.7 (5)C18—Fe2—C20—C1937.5 (3)
C3—C4—C5—N11.8 (7)C22—Fe2—C20—C19170.3 (7)
C3—C4—C5—C6176.2 (4)C16—Fe2—C20—C19119.5 (4)
C10—N2—C6—C71.0 (6)C17—Fe2—C20—C1981.3 (3)
Zn1—N2—C6—C7179.7 (3)C24—Fe2—C20—C16157.6 (3)
C10—N2—C6—C5177.7 (4)C25—Fe2—C20—C16116.4 (3)
Zn1—N2—C6—C51.6 (5)C21—Fe2—C20—C1677.5 (4)
N1—C5—C6—N22.2 (6)C23—Fe2—C20—C16170.4 (5)
C4—C5—C6—N2179.7 (4)C18—Fe2—C20—C1681.9 (3)
N1—C5—C6—C7176.5 (4)C22—Fe2—C20—C1650.8 (9)
C4—C5—C6—C71.7 (7)C17—Fe2—C20—C1638.2 (3)
N2—C6—C7—C81.5 (7)C19—Fe2—C20—C16119.5 (4)
C5—C6—C7—C8177.1 (4)C24—Fe2—C21—C2537.4 (4)
C6—C7—C8—C91.4 (6)C23—Fe2—C21—C2582.1 (4)
C6—C7—C8—C16178.0 (4)C18—Fe2—C21—C25165.8 (5)
C7—C8—C9—C100.9 (6)C20—Fe2—C21—C2571.6 (5)
C16—C8—C9—C10178.5 (4)C22—Fe2—C21—C25120.2 (6)
C6—N2—C10—C90.5 (6)C16—Fe2—C21—C25114.6 (4)
Zn1—N2—C10—C9179.8 (3)C17—Fe2—C21—C25157.8 (4)
C6—N2—C10—C11179.8 (4)C19—Fe2—C21—C2534.7 (9)
Zn1—N2—C10—C110.8 (5)C24—Fe2—C21—C2282.8 (4)
C8—C9—C10—N20.5 (7)C25—Fe2—C21—C22120.2 (6)
C8—C9—C10—C11179.8 (4)C23—Fe2—C21—C2238.1 (4)
C15—N3—C11—C121.9 (7)C18—Fe2—C21—C2245.6 (7)
Zn1—N3—C11—C12170.4 (3)C20—Fe2—C21—C22168.2 (3)
C15—N3—C11—C10178.9 (4)C16—Fe2—C21—C22125.2 (4)
Zn1—N3—C11—C108.7 (5)C17—Fe2—C21—C2282.0 (4)
N2—C10—C11—N35.4 (6)C19—Fe2—C21—C22154.9 (6)
C9—C10—C11—N3173.9 (4)C25—C21—C22—C230.2 (7)
N2—C10—C11—C12173.7 (4)Fe2—C21—C22—C2359.6 (4)
C9—C10—C11—C127.0 (7)C25—C21—C22—Fe259.5 (4)
N3—C11—C12—C131.5 (7)C24—Fe2—C22—C2179.6 (4)
C10—C11—C12—C13179.5 (4)C25—Fe2—C22—C2136.5 (4)
C11—C12—C13—C140.2 (7)C23—Fe2—C22—C21118.5 (6)
C12—C13—C14—C151.3 (7)C18—Fe2—C22—C21160.8 (3)
C11—N3—C15—C140.8 (7)C20—Fe2—C22—C2134.8 (10)
Zn1—N3—C15—C14170.7 (4)C16—Fe2—C22—C2174.5 (4)
C13—C14—C15—N30.8 (8)C17—Fe2—C22—C21117.5 (4)
C9—C8—C16—C17162.3 (4)C19—Fe2—C22—C21160.8 (5)
C7—C8—C16—C1717.1 (7)C24—Fe2—C22—C2338.9 (4)
C9—C8—C16—C2014.5 (7)C25—Fe2—C22—C2382.0 (4)
C7—C8—C16—C20166.1 (4)C21—Fe2—C22—C23118.5 (6)
C9—C8—C16—Fe273.5 (5)C18—Fe2—C22—C2380.7 (5)
C7—C8—C16—Fe2105.9 (5)C20—Fe2—C22—C23153.3 (7)
C24—Fe2—C16—C17167.0 (5)C16—Fe2—C22—C23167.0 (4)
C25—Fe2—C16—C17160.0 (3)C17—Fe2—C22—C23124.0 (4)
C21—Fe2—C16—C17118.3 (3)C19—Fe2—C22—C2342.3 (8)
C23—Fe2—C16—C1746.4 (9)C21—C22—C23—C240.0 (6)
C18—Fe2—C16—C1737.5 (3)Fe2—C22—C23—C2459.8 (4)
C20—Fe2—C16—C17118.4 (4)C21—C22—C23—Fe259.8 (4)
C22—Fe2—C16—C1777.9 (4)C24—Fe2—C23—C22117.5 (6)
C19—Fe2—C16—C1781.1 (3)C25—Fe2—C23—C2280.2 (4)
C24—Fe2—C16—C2048.6 (6)C21—Fe2—C23—C2237.5 (4)
C25—Fe2—C16—C2081.6 (3)C18—Fe2—C23—C22118.5 (4)
C21—Fe2—C16—C20123.3 (3)C20—Fe2—C23—C22162.8 (5)
C23—Fe2—C16—C20164.8 (7)C16—Fe2—C23—C2240.5 (10)
C18—Fe2—C16—C2080.9 (3)C17—Fe2—C23—C2276.9 (5)
C22—Fe2—C16—C20163.7 (3)C19—Fe2—C23—C22161.5 (4)
C17—Fe2—C16—C20118.4 (4)C25—Fe2—C23—C2437.2 (4)
C19—Fe2—C16—C2037.3 (3)C21—Fe2—C23—C2480.0 (4)
C24—Fe2—C16—C871.9 (6)C18—Fe2—C23—C24124.1 (4)
C25—Fe2—C16—C838.9 (5)C20—Fe2—C23—C2445.3 (7)
C21—Fe2—C16—C82.7 (5)C22—Fe2—C23—C24117.5 (6)
C23—Fe2—C16—C874.7 (9)C16—Fe2—C23—C24158.0 (7)
C18—Fe2—C16—C8158.5 (4)C17—Fe2—C23—C24165.7 (4)
C20—Fe2—C16—C8120.6 (5)C19—Fe2—C23—C2481.0 (4)
C22—Fe2—C16—C843.2 (5)C22—C23—C24—C250.2 (7)
C17—Fe2—C16—C8121.1 (5)Fe2—C23—C24—C2560.4 (4)
C19—Fe2—C16—C8157.9 (4)C22—C23—C24—Fe260.6 (4)
C20—C16—C17—C180.3 (5)C21—Fe2—C24—C2537.2 (4)
C8—C16—C17—C18177.1 (4)C23—Fe2—C24—C25118.7 (6)
Fe2—C16—C17—C1858.9 (3)C18—Fe2—C24—C25165.0 (4)
C20—C16—C17—Fe259.2 (3)C20—Fe2—C24—C2582.1 (4)
C8—C16—C17—Fe2118.2 (4)C22—Fe2—C24—C2580.3 (4)
C24—Fe2—C17—C1839.4 (9)C16—Fe2—C24—C2547.8 (7)
C25—Fe2—C17—C18165.3 (5)C17—Fe2—C24—C25164.3 (7)
C21—Fe2—C17—C18159.3 (3)C19—Fe2—C24—C25124.5 (4)
C23—Fe2—C17—C1875.1 (4)C25—Fe2—C24—C23118.7 (6)
C20—Fe2—C17—C1880.9 (3)C21—Fe2—C24—C2381.5 (4)
C22—Fe2—C17—C18117.1 (3)C18—Fe2—C24—C2376.4 (5)
C16—Fe2—C17—C18119.4 (4)C20—Fe2—C24—C23159.2 (4)
C19—Fe2—C17—C1837.2 (3)C22—Fe2—C24—C2338.3 (4)
C24—Fe2—C17—C16158.8 (8)C16—Fe2—C24—C23166.5 (4)
C25—Fe2—C17—C1645.9 (7)C17—Fe2—C24—C2345.6 (10)
C21—Fe2—C17—C1681.3 (4)C19—Fe2—C24—C23116.8 (4)
C23—Fe2—C17—C16165.4 (3)C22—C21—C25—C240.3 (7)
C18—Fe2—C17—C16119.4 (4)Fe2—C21—C25—C2460.1 (4)
C20—Fe2—C17—C1638.6 (3)C22—C21—C25—Fe259.8 (4)
C22—Fe2—C17—C16123.4 (3)C23—C24—C25—C210.3 (7)
C19—Fe2—C17—C1682.2 (3)Fe2—C24—C25—C2160.5 (4)
C16—C17—C18—C191.1 (5)C23—C24—C25—Fe260.2 (4)
Fe2—C17—C18—C1960.0 (3)C24—Fe2—C25—C21119.0 (6)
C16—C17—C18—Fe259.0 (3)C23—Fe2—C25—C2180.6 (4)
C24—Fe2—C18—C17167.4 (3)C18—Fe2—C25—C21162.0 (7)
C25—Fe2—C18—C17160.1 (7)C20—Fe2—C25—C21126.5 (4)
C21—Fe2—C18—C1750.3 (7)C22—Fe2—C25—C2136.8 (4)
C23—Fe2—C18—C17125.2 (3)C16—Fe2—C25—C2183.4 (4)
C20—Fe2—C18—C1782.4 (3)C17—Fe2—C25—C2150.5 (7)
C22—Fe2—C18—C1782.9 (4)C19—Fe2—C25—C21167.4 (4)
C16—Fe2—C18—C1737.8 (3)C21—Fe2—C25—C24119.0 (6)
C19—Fe2—C18—C17120.0 (4)C23—Fe2—C25—C2438.4 (4)
C24—Fe2—C18—C1972.6 (4)C18—Fe2—C25—C2443.0 (10)
C25—Fe2—C18—C1940.1 (9)C20—Fe2—C25—C24114.5 (4)
C21—Fe2—C18—C19170.2 (5)C22—Fe2—C25—C2482.2 (4)
C23—Fe2—C18—C19114.8 (3)C16—Fe2—C25—C24157.6 (4)
C20—Fe2—C18—C1937.5 (3)C17—Fe2—C25—C24169.5 (5)
C22—Fe2—C18—C19157.1 (3)C19—Fe2—C25—C2473.6 (5)
C16—Fe2—C18—C1982.1 (3)

Experimental details

Crystal data
Chemical formula[FeZn(C5H5)Cl2(C20H14N3)]·C2H3N
Mr594.61
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)13.799 (2), 12.998 (2), 14.594 (2)
β (°) 104.514 (4)
V3)2534.0 (6)
Z4
Radiation typeMo Kα
µ (mm1)1.75
Crystal size (mm)0.18 × 0.14 × 0.10
Data collection
DiffractometerBruker APEX area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.743, 0.844
No. of measured, independent and
observed [I > 2σ(I)] reflections
12737, 4938, 3301
Rint0.051
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.131, 1.02
No. of reflections4938
No. of parameters317
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.77, 0.40

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This work was supported by the Science Foundation of Hengyang Normal University of China (10B66), the Scientific Research Fund of Hunan Provincial Education Department (09 K099) and the Science and Technology Foundation of Hengyang (2010kj26).

References

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First citationConstable, E. C., Edwards, A. J., Martinez-Manez, R., Raithby, P. R. & Thompson, A. M. W. C. (1994). J. Chem. Soc. Dalton Trans. pp. 645–650.  CSD CrossRef Web of Science Google Scholar
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First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
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First citationTang, S.-P., Kuang, D.-Z. & Feng, Y.-L. (2009). Acta Cryst. E65, m830.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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