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

Tang, S.-P.; Feng, Y.-L.; Kuang, D.-Z.

doi:10.1107/S1600536811024950

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page m1017

doi:10.1107/S1600536811024950

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

Si-Ping Tang,^a ^* Yong-Lan Feng ^a and Dai-Zhi Kuang ^a

^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 Zn^II atom, one 4′-ferrocenyl-2,2′:6′,2′′-terpyridine (fctpy) ligand, two Cl atoms and one acetonitrile solvent molecule. The Zn^II 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 ); Constable et al. (1994 ); Farlow et al. (1993 ); Tang & Kuang (2007 ); Tang et al. (2009 ).

Experimental

Crystal data

[FeZn(C₅H₅)Cl₂(C₂₀H₁₄N₃)]·C₂H₃N
M_r = 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 ) T_min = 0.743, T_max = 0.844
12737 measured reflections
4938 independent reflections
3301 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.131
S = 1.02
4938 reflections
317 parameters
H-atom parameters constrained
Δρ_max = 0.77 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811024950/jh2301sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811024950/jh2301Isup2.hkl

checkCIF report

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 Au^I, Ru^II, Co^II, Fe^II, Cu^II, and Zn^IIcomplexes (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 Zn^II complex of fctpy is here reported.

In the title complex, the Zn^II 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%).

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

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)]·C₂H₃N	F(000) = 1208
M_r = 594.61	D_x = 1.559 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1833 reflections
a = 13.799 (2) Å	θ = 2.4–21.3°
b = 12.998 (2) Å	µ = 1.75 mm⁻¹
c = 14.594 (2) Å	T = 295 K
β = 104.514 (4)°	Prism, red
V = 2534.0 (6) Å³	0.18 × 0.14 × 0.10 mm
Z = 4

Data collection top

Bruker APEX area-detector diffractometer	4938 independent reflections
Radiation source: fine-focus sealed tube	3301 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→15
T_min = 0.743, T_max = 0.844	k = −14→16
12737 measured reflections	l = −13→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0571P)²] where P = (F_o² + 2F_c²)/3
4938 reflections	(Δ/σ)_max < 0.001
317 parameters	Δρ_max = 0.77 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

[FeZn(C₅H₅)Cl₂(C₂₀H₁₄N₃)]·C₂H₃N	V = 2534.0 (6) Å³
M_r = 594.61	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.799 (2) Å	µ = 1.75 mm⁻¹
b = 12.998 (2) Å	T = 295 K
c = 14.594 (2) Å	0.18 × 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)
T_min = 0.743, T_max = 0.844	R_int = 0.051
12737 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.02	Δρ_max = 0.77 e Å⁻³
4938 reflections	Δρ_min = −0.40 e Å⁻³
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

	x	y	z	U_iso*/U_eq
Fe2	0.15322 (5)	−0.18976 (5)	0.06212 (4)	0.0384 (2)
Zn1	0.27254 (4)	0.38084 (4)	0.02199 (4)	0.04109 (18)
Cl3	0.15301 (10)	0.44465 (10)	−0.10085 (9)	0.0582 (4)
Cl4	0.39084 (10)	0.49174 (10)	0.09763 (10)	0.0595 (4)
N1	0.1865 (3)	0.3817 (3)	0.1303 (3)	0.0410 (9)
N2	0.2663 (3)	0.2268 (3)	0.0618 (3)	0.0353 (9)
N3	0.3560 (3)	0.2940 (3)	−0.0636 (3)	0.0408 (9)
N4	0.4086 (5)	0.6416 (5)	0.4004 (5)	0.116 (2)
C1	0.1444 (4)	0.4648 (4)	0.1587 (4)	0.0522 (13)
H1	0.1497	0.5276	0.1298	0.063*
C2	0.0938 (4)	0.4612 (4)	0.2286 (4)	0.0572 (14)
H2	0.0648	0.5200	0.2466	0.069*
C3	0.0872 (4)	0.3681 (4)	0.2710 (4)	0.0558 (14)
H3	0.0536	0.3637	0.3187	0.067*
C4	0.1298 (4)	0.2809 (4)	0.2437 (3)	0.0476 (12)
H4	0.1262	0.2179	0.2728	0.057*
C5	0.1783 (3)	0.2902 (3)	0.1714 (3)	0.0356 (10)
C6	0.2218 (3)	0.2022 (3)	0.1314 (3)	0.0347 (10)
C7	0.2165 (3)	0.1017 (3)	0.1600 (3)	0.0366 (10)
H7	0.1869	0.0863	0.2090	0.044*
C8	0.2560 (3)	0.0232 (3)	0.1149 (3)	0.0370 (10)
C9	0.3017 (3)	0.0500 (3)	0.0432 (3)	0.0421 (11)
H9	0.3296	−0.0004	0.0125	0.050*
C10	0.3053 (3)	0.1532 (3)	0.0181 (3)	0.0361 (10)
C11	0.3525 (3)	0.1907 (3)	−0.0571 (3)	0.0375 (11)
C12	0.3885 (4)	0.1273 (4)	−0.1163 (3)	0.0476 (12)
H12	0.3840	0.0562	−0.1116	0.057*
C13	0.4318 (4)	0.1714 (4)	−0.1834 (3)	0.0499 (13)
H13	0.4564	0.1299	−0.2243	0.060*
C14	0.4378 (4)	0.2756 (4)	−0.1888 (3)	0.0507 (13)
H14	0.4676	0.3066	−0.2323	0.061*
C15	0.3984 (4)	0.3343 (4)	−0.1278 (3)	0.0495 (13)
H15	0.4016	0.4056	−0.1318	0.059*
C16	0.2486 (3)	−0.0851 (3)	0.1418 (3)	0.0370 (11)
C17	0.1829 (4)	−0.1262 (3)	0.1942 (3)	0.0435 (12)
H17	0.1358	−0.0868	0.2208	0.052*
C18	0.1969 (4)	−0.2339 (4)	0.1999 (3)	0.0539 (14)
H18	0.1604	−0.2818	0.2310	0.065*
C19	0.2716 (4)	−0.2618 (4)	0.1534 (4)	0.0510 (13)
H19	0.2959	−0.3315	0.1467	0.061*
C20	0.3029 (4)	−0.1705 (3)	0.1163 (3)	0.0462 (12)
H20	0.3532	−0.1661	0.0795	0.055*
C21	0.0683 (5)	−0.1180 (5)	−0.0538 (4)	0.0713 (15)
H21	0.0689	−0.0439	−0.0664	0.086*
C22	0.0069 (5)	−0.1663 (5)	−0.0061 (4)	0.0748 (15)
H22	−0.0439	−0.1334	0.0203	0.090*
C23	0.0298 (5)	−0.2713 (5)	−0.0031 (5)	0.0820 (16)
H23	−0.0024	−0.3259	0.0250	0.098*
C24	0.1066 (5)	−0.2835 (5)	−0.0504 (4)	0.0818 (17)
H24	0.1378	−0.3487	−0.0610	0.098*
C25	0.1287 (5)	−0.1888 (5)	−0.0803 (4)	0.0752 (15)
H25	0.1790	−0.1744	−0.1156	0.090*
C26	0.4023 (5)	0.7265 (5)	0.4002 (4)	0.0667 (16)
C27	0.3915 (5)	0.8365 (5)	0.3999 (5)	0.089 (2)
H27A	0.3598	0.8594	0.3370	0.133*
H27B	0.4563	0.8678	0.4206	0.133*
H27C	0.3511	0.8556	0.4421	0.133*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe2	0.0469 (4)	0.0330 (4)	0.0339 (4)	−0.0007 (3)	0.0076 (3)	−0.0003 (3)
Zn1	0.0501 (4)	0.0310 (3)	0.0439 (3)	−0.0017 (2)	0.0149 (3)	0.0001 (2)
Cl3	0.0724 (9)	0.0544 (8)	0.0457 (8)	0.0163 (7)	0.0108 (6)	0.0017 (6)
Cl4	0.0604 (9)	0.0472 (7)	0.0716 (9)	−0.0133 (6)	0.0179 (7)	−0.0126 (7)
N1	0.050 (2)	0.029 (2)	0.047 (2)	−0.0023 (17)	0.0170 (19)	−0.0052 (18)
N2	0.035 (2)	0.0300 (19)	0.042 (2)	0.0019 (16)	0.0121 (17)	−0.0020 (17)
N3	0.046 (2)	0.041 (2)	0.039 (2)	−0.0018 (18)	0.0165 (18)	0.0009 (18)
N4	0.154 (7)	0.072 (4)	0.113 (6)	0.000 (4)	0.018 (5)	0.012 (4)
C1	0.069 (4)	0.033 (3)	0.056 (3)	0.004 (2)	0.018 (3)	−0.004 (2)
C2	0.067 (4)	0.050 (3)	0.059 (4)	0.012 (3)	0.025 (3)	−0.010 (3)
C3	0.064 (4)	0.061 (3)	0.051 (3)	0.010 (3)	0.031 (3)	−0.003 (3)
C4	0.062 (3)	0.042 (3)	0.043 (3)	0.001 (2)	0.020 (3)	0.002 (2)
C5	0.037 (3)	0.035 (2)	0.034 (3)	−0.0047 (19)	0.008 (2)	−0.003 (2)
C6	0.034 (3)	0.032 (2)	0.038 (3)	−0.0028 (19)	0.010 (2)	0.000 (2)
C7	0.038 (3)	0.037 (3)	0.034 (2)	−0.001 (2)	0.008 (2)	−0.002 (2)
C8	0.036 (3)	0.036 (2)	0.037 (3)	−0.006 (2)	0.005 (2)	−0.001 (2)
C9	0.051 (3)	0.034 (2)	0.042 (3)	0.004 (2)	0.015 (2)	−0.003 (2)
C10	0.034 (3)	0.036 (2)	0.039 (3)	0.000 (2)	0.010 (2)	−0.001 (2)
C11	0.040 (3)	0.035 (3)	0.038 (3)	0.001 (2)	0.011 (2)	−0.002 (2)
C12	0.055 (3)	0.046 (3)	0.046 (3)	−0.001 (2)	0.019 (2)	−0.007 (2)
C13	0.050 (3)	0.057 (3)	0.048 (3)	0.007 (2)	0.021 (2)	−0.006 (3)
C14	0.053 (3)	0.067 (4)	0.038 (3)	−0.005 (3)	0.022 (2)	0.004 (3)
C15	0.051 (3)	0.048 (3)	0.051 (3)	−0.002 (2)	0.015 (3)	0.003 (3)
C16	0.046 (3)	0.027 (2)	0.035 (3)	−0.0047 (19)	0.006 (2)	−0.0026 (19)
C17	0.057 (3)	0.040 (3)	0.033 (3)	−0.008 (2)	0.011 (2)	−0.002 (2)
C18	0.079 (4)	0.038 (3)	0.041 (3)	−0.011 (3)	0.009 (3)	0.007 (2)
C19	0.058 (3)	0.030 (3)	0.058 (3)	0.005 (2)	0.001 (3)	0.001 (2)
C20	0.047 (3)	0.035 (3)	0.055 (3)	−0.001 (2)	0.010 (2)	0.002 (2)
C21	0.082 (3)	0.071 (3)	0.048 (3)	0.004 (3)	−0.008 (2)	0.006 (3)
C22	0.061 (3)	0.097 (3)	0.057 (3)	0.008 (3)	−0.004 (2)	−0.008 (3)
C23	0.076 (3)	0.086 (3)	0.065 (3)	−0.030 (3)	−0.018 (3)	0.007 (3)
C24	0.088 (3)	0.073 (3)	0.061 (3)	0.017 (3)	−0.025 (3)	−0.033 (3)
C25	0.079 (3)	0.094 (3)	0.045 (3)	0.003 (3)	0.001 (2)	−0.012 (3)
C26	0.077 (4)	0.073 (4)	0.049 (4)	−0.007 (3)	0.014 (3)	0.005 (3)
C27	0.100 (5)	0.073 (5)	0.083 (5)	−0.015 (4)	0.003 (4)	−0.007 (4)

Geometric parameters (Å, º) top

Fe2—C24	2.017 (5)	C8—C16	1.471 (6)
Fe2—C25	2.020 (6)	C9—C10	1.394 (6)
Fe2—C21	2.028 (5)	C9—H9	0.9300
Fe2—C23	2.029 (5)	C10—C11	1.491 (6)
Fe2—C18	2.031 (5)	C11—C12	1.374 (6)
Fe2—C20	2.034 (5)	C12—C13	1.393 (6)
Fe2—C22	2.038 (6)	C12—H12	0.9300
Fe2—C16	2.041 (4)	C13—C14	1.361 (7)
Fe2—C17	2.042 (5)	C13—H13	0.9300
Fe2—C19	2.056 (5)	C14—C15	1.384 (7)
Zn1—N2	2.093 (3)	C14—H14	0.9300
Zn1—N1	2.202 (4)	C15—H15	0.9300
Zn1—N3	2.210 (4)	C16—C17	1.429 (6)
Zn1—Cl4	2.2490 (13)	C16—C20	1.439 (6)
Zn1—Cl3	2.2672 (14)	C17—C18	1.412 (6)
N1—C1	1.340 (6)	C17—H17	0.9800
N1—C5	1.350 (5)	C18—C19	1.416 (7)
N2—C10	1.335 (5)	C18—H18	0.9800
N2—C6	1.350 (5)	C19—C20	1.416 (6)
N3—C15	1.329 (6)	C19—H19	0.9800
N3—C11	1.348 (5)	C20—H20	0.9800
N4—C26	1.107 (8)	C21—C25	1.361 (8)
C1—C2	1.374 (7)	C21—C22	1.376 (8)
C1—H1	0.9300	C21—H21	0.9800
C2—C3	1.372 (7)	C22—C23	1.399 (8)
C2—H2	0.9300	C22—H22	0.9800
C3—C4	1.381 (6)	C23—C24	1.412 (9)
C3—H3	0.9300	C23—H23	0.9800
C4—C5	1.389 (6)	C24—C25	1.366 (8)
C4—H4	0.9300	C24—H24	0.9800
C5—C6	1.479 (6)	C25—H25	0.9800
C6—C7	1.379 (6)	C26—C27	1.437 (8)
C7—C8	1.397 (6)	C27—H27A	0.9600
C7—H7	0.9300	C27—H27B	0.9600
C8—C9	1.396 (6)	C27—H27C	0.9600

C24—Fe2—C25	39.5 (2)	C10—C9—C8	119.3 (4)
C24—Fe2—C21	66.3 (2)	C10—C9—H9	120.3
C25—Fe2—C21	39.3 (2)	C8—C9—H9	120.3
C24—Fe2—C23	40.9 (3)	N2—C10—C9	121.3 (4)
C25—Fe2—C23	67.5 (3)	N2—C10—C11	114.8 (4)
C21—Fe2—C23	66.9 (3)	C9—C10—C11	123.9 (4)
C24—Fe2—C18	126.2 (2)	N3—C11—C12	121.9 (4)
C25—Fe2—C18	162.1 (2)	N3—C11—C10	114.1 (4)
C21—Fe2—C18	157.2 (3)	C12—C11—C10	124.0 (4)
C23—Fe2—C18	108.8 (2)	C11—C12—C13	118.8 (5)
C24—Fe2—C20	118.5 (2)	C11—C12—H12	120.6
C25—Fe2—C20	106.9 (2)	C13—C12—H12	120.6
C21—Fe2—C20	125.9 (2)	C14—C13—C12	119.6 (5)
C23—Fe2—C20	153.9 (2)	C14—C13—H13	120.2
C18—Fe2—C20	68.3 (2)	C12—C13—H13	120.2
C24—Fe2—C22	67.5 (3)	C13—C14—C15	118.1 (5)
C25—Fe2—C22	66.8 (3)	C13—C14—H14	120.9
C21—Fe2—C22	39.6 (2)	C15—C14—H14	120.9
C23—Fe2—C22	40.2 (2)	N3—C15—C14	123.3 (5)
C18—Fe2—C22	122.5 (3)	N3—C15—H15	118.3
C20—Fe2—C22	163.1 (2)	C14—C15—H15	118.3
C24—Fe2—C16	153.5 (3)	C17—C16—C20	106.9 (4)
C25—Fe2—C16	120.0 (2)	C17—C16—C8	126.6 (4)
C21—Fe2—C16	108.9 (2)	C20—C16—C8	126.4 (4)
C23—Fe2—C16	163.9 (3)	C17—C16—Fe2	69.6 (2)
C18—Fe2—C16	68.64 (18)	C20—C16—Fe2	69.0 (2)
C20—Fe2—C16	41.35 (17)	C8—C16—Fe2	124.3 (3)
C22—Fe2—C16	126.7 (2)	C18—C17—C16	107.8 (4)
C24—Fe2—C17	163.9 (3)	C18—C17—Fe2	69.3 (3)
C25—Fe2—C17	155.6 (2)	C16—C17—Fe2	69.5 (3)
C21—Fe2—C17	122.6 (2)	C18—C17—H17	126.1
C23—Fe2—C17	126.9 (3)	C16—C17—H17	126.1
C18—Fe2—C17	40.57 (18)	Fe2—C17—H17	126.1
C20—Fe2—C17	68.8 (2)	C17—C18—C19	109.3 (4)
C22—Fe2—C17	109.9 (2)	C17—C18—Fe2	70.1 (3)
C16—Fe2—C17	40.96 (17)	C19—C18—Fe2	70.7 (3)
C24—Fe2—C19	107.0 (2)	C17—C18—H18	125.3
C25—Fe2—C19	124.8 (2)	C19—C18—H18	125.3
C21—Fe2—C19	161.6 (3)	Fe2—C18—H18	125.3
C23—Fe2—C19	120.2 (2)	C18—C19—C20	107.3 (4)
C18—Fe2—C19	40.5 (2)	C18—C19—Fe2	68.8 (3)
C20—Fe2—C19	40.51 (18)	C20—C19—Fe2	68.9 (3)
C22—Fe2—C19	156.0 (2)	C18—C19—H19	126.4
C16—Fe2—C19	68.93 (18)	C20—C19—H19	126.4
C17—Fe2—C19	68.5 (2)	Fe2—C19—H19	126.4
N2—Zn1—N1	74.85 (13)	C19—C20—C16	108.6 (4)
N2—Zn1—N3	74.46 (14)	C19—C20—Fe2	70.6 (3)
N1—Zn1—N3	149.31 (13)	C16—C20—Fe2	69.6 (3)
N2—Zn1—Cl4	123.51 (10)	C19—C20—H20	125.7
N1—Zn1—Cl4	95.74 (10)	C16—C20—H20	125.7
N3—Zn1—Cl4	100.82 (10)	Fe2—C20—H20	125.7
N2—Zn1—Cl3	119.82 (10)	C25—C21—C22	109.4 (6)
N1—Zn1—Cl3	98.58 (11)	C25—C21—Fe2	70.0 (4)
N3—Zn1—Cl3	96.82 (10)	C22—C21—Fe2	70.6 (3)
Cl4—Zn1—Cl3	116.64 (5)	C25—C21—H21	125.3
C1—N1—C5	118.8 (4)	C22—C21—H21	125.3
C1—N1—Zn1	125.4 (3)	Fe2—C21—H21	125.3
C5—N1—Zn1	115.7 (3)	C21—C22—C23	107.4 (6)
C10—N2—C6	120.2 (4)	C21—C22—Fe2	69.8 (3)
C10—N2—Zn1	120.2 (3)	C23—C22—Fe2	69.6 (3)
C6—N2—Zn1	119.6 (3)	C21—C22—H22	126.3
C15—N3—C11	118.2 (4)	C23—C22—H22	126.3
C15—N3—Zn1	125.5 (3)	Fe2—C22—H22	126.3
C11—N3—Zn1	115.8 (3)	C22—C23—C24	106.5 (6)
N1—C1—C2	122.8 (5)	C22—C23—Fe2	70.2 (3)
N1—C1—H1	118.6	C24—C23—Fe2	69.1 (3)
C2—C1—H1	118.6	C22—C23—H23	126.7
C3—C2—C1	117.9 (5)	C24—C23—H23	126.7
C3—C2—H2	121.0	Fe2—C23—H23	126.7
C1—C2—H2	121.0	C25—C24—C23	108.1 (6)
C2—C3—C4	120.8 (5)	C25—C24—Fe2	70.4 (3)
C2—C3—H3	119.6	C23—C24—Fe2	70.1 (3)
C4—C3—H3	119.6	C25—C24—H24	126.0
C3—C4—C5	118.0 (5)	C23—C24—H24	126.0
C3—C4—H4	121.0	Fe2—C24—H24	126.0
C5—C4—H4	121.0	C21—C25—C24	108.5 (6)
N1—C5—C4	121.6 (4)	C21—C25—Fe2	70.7 (4)
N1—C5—C6	114.8 (4)	C24—C25—Fe2	70.1 (4)
C4—C5—C6	123.6 (4)	C21—C25—H25	125.7
N2—C6—C7	121.4 (4)	C24—C25—H25	125.7
N2—C6—C5	114.8 (4)	Fe2—C25—H25	125.7
C7—C6—C5	123.8 (4)	N4—C26—C27	178.5 (8)
C6—C7—C8	119.5 (4)	C26—C27—H27A	109.5
C6—C7—H7	120.2	C26—C27—H27B	109.5
C8—C7—H7	120.2	H27A—C27—H27B	109.5
C9—C8—C7	118.2 (4)	C26—C27—H27C	109.5
C9—C8—C16	120.9 (4)	H27A—C27—H27C	109.5
C7—C8—C16	120.8 (4)	H27B—C27—H27C	109.5

N2—Zn1—N1—C1	−177.1 (4)	C17—Fe2—C18—C19	−120.0 (4)
N3—Zn1—N1—C1	−177.7 (3)	C17—C18—C19—C20	−1.4 (6)
Cl4—Zn1—N1—C1	59.7 (4)	Fe2—C18—C19—C20	58.3 (3)
Cl3—Zn1—N1—C1	−58.4 (4)	C17—C18—C19—Fe2	−59.7 (3)
N2—Zn1—N1—C5	4.2 (3)	C24—Fe2—C19—C18	−126.3 (4)
N3—Zn1—N1—C5	3.6 (5)	C25—Fe2—C19—C18	−166.0 (3)
Cl4—Zn1—N1—C5	−119.0 (3)	C21—Fe2—C19—C18	167.9 (6)
Cl3—Zn1—N1—C5	122.9 (3)	C23—Fe2—C19—C18	−83.8 (4)
N1—Zn1—N2—C10	176.3 (3)	C20—Fe2—C19—C18	119.4 (4)
N3—Zn1—N2—C10	−4.1 (3)	C22—Fe2—C19—C18	−53.6 (7)
Cl4—Zn1—N2—C10	−96.9 (3)	C16—Fe2—C19—C18	81.4 (3)
Cl3—Zn1—N2—C10	85.0 (3)	C17—Fe2—C19—C18	37.3 (3)
N1—Zn1—N2—C6	−3.1 (3)	C24—Fe2—C19—C20	114.2 (4)
N3—Zn1—N2—C6	176.6 (3)	C25—Fe2—C19—C20	74.5 (4)
Cl4—Zn1—N2—C6	83.8 (3)	C21—Fe2—C19—C20	48.5 (8)
Cl3—Zn1—N2—C6	−94.4 (3)	C23—Fe2—C19—C20	156.7 (4)
N2—Zn1—N3—C15	178.7 (4)	C18—Fe2—C19—C20	−119.4 (4)
N1—Zn1—N3—C15	179.3 (3)	C22—Fe2—C19—C20	−173.1 (5)
Cl4—Zn1—N3—C15	−59.3 (4)	C16—Fe2—C19—C20	−38.1 (3)
Cl3—Zn1—N3—C15	59.6 (4)	C17—Fe2—C19—C20	−82.2 (3)
N2—Zn1—N3—C11	7.0 (3)	C18—C19—C20—C16	1.2 (6)
N1—Zn1—N3—C11	7.6 (5)	Fe2—C19—C20—C16	59.4 (3)
Cl4—Zn1—N3—C11	129.0 (3)	C18—C19—C20—Fe2	−58.3 (3)
Cl3—Zn1—N3—C11	−112.1 (3)	C17—C16—C20—C19	−0.6 (5)
C5—N1—C1—C2	0.5 (7)	C8—C16—C20—C19	−177.9 (4)
Zn1—N1—C1—C2	−178.2 (4)	Fe2—C16—C20—C19	−60.1 (3)
N1—C1—C2—C3	0.5 (8)	C17—C16—C20—Fe2	59.5 (3)
C1—C2—C3—C4	−0.3 (8)	C8—C16—C20—Fe2	−117.9 (4)
C2—C3—C4—C5	−0.8 (8)	C24—Fe2—C20—C19	−82.9 (4)
C1—N1—C5—C4	−1.7 (7)	C25—Fe2—C20—C19	−124.2 (3)
Zn1—N1—C5—C4	177.1 (3)	C21—Fe2—C20—C19	−163.1 (3)
C1—N1—C5—C6	176.5 (4)	C23—Fe2—C20—C19	−51.0 (7)
Zn1—N1—C5—C6	−4.7 (5)	C18—Fe2—C20—C19	37.5 (3)
C3—C4—C5—N1	1.8 (7)	C22—Fe2—C20—C19	170.3 (7)
C3—C4—C5—C6	−176.2 (4)	C16—Fe2—C20—C19	119.5 (4)
C10—N2—C6—C7	1.0 (6)	C17—Fe2—C20—C19	81.3 (3)
Zn1—N2—C6—C7	−179.7 (3)	C24—Fe2—C20—C16	157.6 (3)
C10—N2—C6—C5	−177.7 (4)	C25—Fe2—C20—C16	116.4 (3)
Zn1—N2—C6—C5	1.6 (5)	C21—Fe2—C20—C16	77.5 (4)
N1—C5—C6—N2	2.2 (6)	C23—Fe2—C20—C16	−170.4 (5)
C4—C5—C6—N2	−179.7 (4)	C18—Fe2—C20—C16	−81.9 (3)
N1—C5—C6—C7	−176.5 (4)	C22—Fe2—C20—C16	50.8 (9)
C4—C5—C6—C7	1.7 (7)	C17—Fe2—C20—C16	−38.2 (3)
N2—C6—C7—C8	−1.5 (7)	C19—Fe2—C20—C16	−119.5 (4)
C5—C6—C7—C8	177.1 (4)	C24—Fe2—C21—C25	−37.4 (4)
C6—C7—C8—C9	1.4 (6)	C23—Fe2—C21—C25	−82.1 (4)
C6—C7—C8—C16	−178.0 (4)	C18—Fe2—C21—C25	−165.8 (5)
C7—C8—C9—C10	−0.9 (6)	C20—Fe2—C21—C25	71.6 (5)
C16—C8—C9—C10	178.5 (4)	C22—Fe2—C21—C25	−120.2 (6)
C6—N2—C10—C9	−0.5 (6)	C16—Fe2—C21—C25	114.6 (4)
Zn1—N2—C10—C9	−179.8 (3)	C17—Fe2—C21—C25	157.8 (4)
C6—N2—C10—C11	−179.8 (4)	C19—Fe2—C21—C25	34.7 (9)
Zn1—N2—C10—C11	0.8 (5)	C24—Fe2—C21—C22	82.8 (4)
C8—C9—C10—N2	0.5 (7)	C25—Fe2—C21—C22	120.2 (6)
C8—C9—C10—C11	179.8 (4)	C23—Fe2—C21—C22	38.1 (4)
C15—N3—C11—C12	−1.9 (7)	C18—Fe2—C21—C22	−45.6 (7)
Zn1—N3—C11—C12	170.4 (3)	C20—Fe2—C21—C22	−168.2 (3)
C15—N3—C11—C10	178.9 (4)	C16—Fe2—C21—C22	−125.2 (4)
Zn1—N3—C11—C10	−8.7 (5)	C17—Fe2—C21—C22	−82.0 (4)
N2—C10—C11—N3	5.4 (6)	C19—Fe2—C21—C22	154.9 (6)
C9—C10—C11—N3	−173.9 (4)	C25—C21—C22—C23	−0.2 (7)
N2—C10—C11—C12	−173.7 (4)	Fe2—C21—C22—C23	−59.6 (4)
C9—C10—C11—C12	7.0 (7)	C25—C21—C22—Fe2	59.5 (4)
N3—C11—C12—C13	1.5 (7)	C24—Fe2—C22—C21	−79.6 (4)
C10—C11—C12—C13	−179.5 (4)	C25—Fe2—C22—C21	−36.5 (4)
C11—C12—C13—C14	0.2 (7)	C23—Fe2—C22—C21	−118.5 (6)
C12—C13—C14—C15	−1.3 (7)	C18—Fe2—C22—C21	160.8 (3)
C11—N3—C15—C14	0.8 (7)	C20—Fe2—C22—C21	34.8 (10)
Zn1—N3—C15—C14	−170.7 (4)	C16—Fe2—C22—C21	74.5 (4)
C13—C14—C15—N3	0.8 (8)	C17—Fe2—C22—C21	117.5 (4)
C9—C8—C16—C17	−162.3 (4)	C19—Fe2—C22—C21	−160.8 (5)
C7—C8—C16—C17	17.1 (7)	C24—Fe2—C22—C23	38.9 (4)
C9—C8—C16—C20	14.5 (7)	C25—Fe2—C22—C23	82.0 (4)
C7—C8—C16—C20	−166.1 (4)	C21—Fe2—C22—C23	118.5 (6)
C9—C8—C16—Fe2	−73.5 (5)	C18—Fe2—C22—C23	−80.7 (5)
C7—C8—C16—Fe2	105.9 (5)	C20—Fe2—C22—C23	153.3 (7)
C24—Fe2—C16—C17	−167.0 (5)	C16—Fe2—C22—C23	−167.0 (4)
C25—Fe2—C16—C17	160.0 (3)	C17—Fe2—C22—C23	−124.0 (4)
C21—Fe2—C16—C17	118.3 (3)	C19—Fe2—C22—C23	−42.3 (8)
C23—Fe2—C16—C17	46.4 (9)	C21—C22—C23—C24	0.0 (6)
C18—Fe2—C16—C17	−37.5 (3)	Fe2—C22—C23—C24	−59.8 (4)
C20—Fe2—C16—C17	−118.4 (4)	C21—C22—C23—Fe2	59.8 (4)
C22—Fe2—C16—C17	77.9 (4)	C24—Fe2—C23—C22	−117.5 (6)
C19—Fe2—C16—C17	−81.1 (3)	C25—Fe2—C23—C22	−80.2 (4)
C24—Fe2—C16—C20	−48.6 (6)	C21—Fe2—C23—C22	−37.5 (4)
C25—Fe2—C16—C20	−81.6 (3)	C18—Fe2—C23—C22	118.5 (4)
C21—Fe2—C16—C20	−123.3 (3)	C20—Fe2—C23—C22	−162.8 (5)
C23—Fe2—C16—C20	164.8 (7)	C16—Fe2—C23—C22	40.5 (10)
C18—Fe2—C16—C20	80.9 (3)	C17—Fe2—C23—C22	76.9 (5)
C22—Fe2—C16—C20	−163.7 (3)	C19—Fe2—C23—C22	161.5 (4)
C17—Fe2—C16—C20	118.4 (4)	C25—Fe2—C23—C24	37.2 (4)
C19—Fe2—C16—C20	37.3 (3)	C21—Fe2—C23—C24	80.0 (4)
C24—Fe2—C16—C8	71.9 (6)	C18—Fe2—C23—C24	−124.1 (4)
C25—Fe2—C16—C8	38.9 (5)	C20—Fe2—C23—C24	−45.3 (7)
C21—Fe2—C16—C8	−2.7 (5)	C22—Fe2—C23—C24	117.5 (6)
C23—Fe2—C16—C8	−74.7 (9)	C16—Fe2—C23—C24	158.0 (7)
C18—Fe2—C16—C8	−158.5 (4)	C17—Fe2—C23—C24	−165.7 (4)
C20—Fe2—C16—C8	120.6 (5)	C19—Fe2—C23—C24	−81.0 (4)
C22—Fe2—C16—C8	−43.2 (5)	C22—C23—C24—C25	0.2 (7)
C17—Fe2—C16—C8	−121.1 (5)	Fe2—C23—C24—C25	−60.4 (4)
C19—Fe2—C16—C8	157.9 (4)	C22—C23—C24—Fe2	60.6 (4)
C20—C16—C17—C18	−0.3 (5)	C21—Fe2—C24—C25	37.2 (4)
C8—C16—C17—C18	177.1 (4)	C23—Fe2—C24—C25	118.7 (6)
Fe2—C16—C17—C18	58.9 (3)	C18—Fe2—C24—C25	−165.0 (4)
C20—C16—C17—Fe2	−59.2 (3)	C20—Fe2—C24—C25	−82.1 (4)
C8—C16—C17—Fe2	118.2 (4)	C22—Fe2—C24—C25	80.3 (4)
C24—Fe2—C17—C18	39.4 (9)	C16—Fe2—C24—C25	−47.8 (7)
C25—Fe2—C17—C18	−165.3 (5)	C17—Fe2—C24—C25	164.3 (7)
C21—Fe2—C17—C18	159.3 (3)	C19—Fe2—C24—C25	−124.5 (4)
C23—Fe2—C17—C18	75.1 (4)	C25—Fe2—C24—C23	−118.7 (6)
C20—Fe2—C17—C18	−80.9 (3)	C21—Fe2—C24—C23	−81.5 (4)
C22—Fe2—C17—C18	117.1 (3)	C18—Fe2—C24—C23	76.4 (5)
C16—Fe2—C17—C18	−119.4 (4)	C20—Fe2—C24—C23	159.2 (4)
C19—Fe2—C17—C18	−37.2 (3)	C22—Fe2—C24—C23	−38.3 (4)
C24—Fe2—C17—C16	158.8 (8)	C16—Fe2—C24—C23	−166.5 (4)
C25—Fe2—C17—C16	−45.9 (7)	C17—Fe2—C24—C23	45.6 (10)
C21—Fe2—C17—C16	−81.3 (4)	C19—Fe2—C24—C23	116.8 (4)
C23—Fe2—C17—C16	−165.4 (3)	C22—C21—C25—C24	0.3 (7)
C18—Fe2—C17—C16	119.4 (4)	Fe2—C21—C25—C24	60.1 (4)
C20—Fe2—C17—C16	38.6 (3)	C22—C21—C25—Fe2	−59.8 (4)
C22—Fe2—C17—C16	−123.4 (3)	C23—C24—C25—C21	−0.3 (7)
C19—Fe2—C17—C16	82.2 (3)	Fe2—C24—C25—C21	−60.5 (4)
C16—C17—C18—C19	1.1 (5)	C23—C24—C25—Fe2	60.2 (4)
Fe2—C17—C18—C19	60.0 (3)	C24—Fe2—C25—C21	119.0 (6)
C16—C17—C18—Fe2	−59.0 (3)	C23—Fe2—C25—C21	80.6 (4)
C24—Fe2—C18—C17	−167.4 (3)	C18—Fe2—C25—C21	162.0 (7)
C25—Fe2—C18—C17	160.1 (7)	C20—Fe2—C25—C21	−126.5 (4)
C21—Fe2—C18—C17	−50.3 (7)	C22—Fe2—C25—C21	36.8 (4)
C23—Fe2—C18—C17	−125.2 (3)	C16—Fe2—C25—C21	−83.4 (4)
C20—Fe2—C18—C17	82.4 (3)	C17—Fe2—C25—C21	−50.5 (7)
C22—Fe2—C18—C17	−82.9 (4)	C19—Fe2—C25—C21	−167.4 (4)
C16—Fe2—C18—C17	37.8 (3)	C21—Fe2—C25—C24	−119.0 (6)
C19—Fe2—C18—C17	120.0 (4)	C23—Fe2—C25—C24	−38.4 (4)
C24—Fe2—C18—C19	72.6 (4)	C18—Fe2—C25—C24	43.0 (10)
C25—Fe2—C18—C19	40.1 (9)	C20—Fe2—C25—C24	114.5 (4)
C21—Fe2—C18—C19	−170.2 (5)	C22—Fe2—C25—C24	−82.2 (4)
C23—Fe2—C18—C19	114.8 (3)	C16—Fe2—C25—C24	157.6 (4)
C20—Fe2—C18—C19	−37.5 (3)	C17—Fe2—C25—C24	−169.5 (5)
C22—Fe2—C18—C19	157.1 (3)	C19—Fe2—C25—C24	73.6 (5)
C16—Fe2—C18—C19	−82.1 (3)

Experimental details

Crystal data
Chemical formula	[FeZn(C₅H₅)Cl₂(C₂₀H₁₄N₃)]·C₂H₃N
M_r	594.61
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	13.799 (2), 12.998 (2), 14.594 (2)
β (°)	104.514 (4)
V (Å³)	2534.0 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.75
Crystal size (mm)	0.18 × 0.14 × 0.10

Data collection
Diffractometer	Bruker APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.743, 0.844
No. of measured, independent and observed [I > 2σ(I)] reflections	12737, 4938, 3301
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.131, 1.02
No. of reflections	4938
No. of parameters	317
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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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