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

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ISSN: 2056-9890

[2,6-Bis(6-methyl­quinolin-2-yl)pyridine-κ3N,N′,N′′]di­chloridoiron(II)

aDepartment of Chemistry, Shaanxi Key Laboratory for Physico-Inorganic Chemistry, Northwest University, Xi'an 710069, People's Republic of China, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 15 September 2010; accepted 16 September 2010; online 25 September 2010)

In the mol­ecule of the title compound, [FeCl2(C25H19N3)], the three N atoms span the axial–equatorial–axial sites of the trigonal-bipyramidal coordination polyhedron; the geometry of the FeII atom is 32% distorted from trigonal-bipyramidal (towards square-pyramidal along the Berry pseudorotation pathway). One of the Cl atoms is disordered over two positions in a 0.938 (11):0.062 (11) ratio. Inter­molecular C—H⋯Cl hydrogen bonding occurs in the crystal structure.

Related literature

For the synthesis of the N-heterocyclic ligand, see: Buu-Hoi et al. (1965[Buu-Hoi, N. P., Perin, F. & Jacquignon, P. (1965). J. Heterocycl. Chem. 2, 7-10.]). For a related structure, see: Li et al. (2010[Li, X.-P., Liu, Y.-Y. & Zhao, J.-S. (2010). Acta Cryst. E66, m1215.]).

[Scheme 1]

Experimental

Crystal data
  • [FeCl2(C25H19N3)]

  • Mr = 488.18

  • Triclinic, [P \overline 1]

  • a = 9.6228 (7) Å

  • b = 10.2558 (8) Å

  • c = 10.7324 (8) Å

  • α = 94.352 (1)°

  • β = 95.481 (1)°

  • γ = 96.121 (1)°

  • V = 1044.35 (14) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.00 mm−1

  • T = 100 K

  • 0.30 × 0.10 × 0.05 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.754, Tmax = 0.952

  • 9910 measured reflections

  • 4757 independent reflections

  • 3954 reflections with I > 2σ(I)

  • Rint = 0.024

Refinement
  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.108

  • S = 1.05

  • 4757 reflections

  • 292 parameters

  • 7 restraints

  • H-atom parameters constrained

  • Δρmax = 0.54 e Å−3

  • Δρmin = −0.44 e Å−3

Table 1
Selected bond lengths (Å)

Fe1—N1 2.2386 (19)
Fe1—N2 2.103 (2)
Fe1—N3 2.2523 (19)
Fe1—Cl1 2.3636 (8)
Fe1—Cl2 2.2748 (7)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C8—H8⋯Cl2i 0.95 2.70 3.561 (2) 151
C17—H17⋯Cl1ii 0.95 2.73 3.538 (4) 144
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

A recent study reported the chromium(III) chloride adduct of 2,6-bis(p-bromphenylimino)pyridine; the N-heterocycle chelates to the metal atom in a terdentate manner (Li et al., 2010). Bis[2'-(6-methylquinolinyl)]pyridine has a similar set of donor sites capable of binding in this manner, as demonstrated in the present iron dichloride adduct (Scheme I, Fig. 1 and Table 1). In the molecule of FeCl2(C25H19N3), the three N atoms span the axial–equatorial-axial sites of the trigonal bipyramidal coordination polyhedron; the geometry of Fe is 32% distorted from the trigonal bipyramid along the Berry pseudorotation pathway. Intermolecular C—H···Cl hydrogen bonding occurs in the crystal structure (Table 2).

Related literature top

For the synthesis of the N-heterocyclic ligand, see: Buu-Hoi et al. (1965). For a related structure, see: Li et al. (2010).

Experimental top

The ligand was synthesized by using a literature procedure (Buu-Hoi et al., 1965).

Bis[2'-(6-methylquinolinyl)]pyridine (0.018 g, 0.05 mmol), and ferrous chloride tetrahydrate (0.02 g, 0.05 mmol) along with five drops of 1 M hydrochloric acid were dissolved in ethanol (10 ml). The mixture was heated in a Teflon-lined, stainless-steel Parr bomb at 363 K for 120 h. The bomb was cooled at 5 K per hour. Black crystals were isolated.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95–0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C).

One of the chlorine atoms is disordered over two positions in a 0.938 (11):0.062 (11) ratio. The Fe–Cl pair of distances were restrained to within 0.01 Å of each other; the anisotropic temperature factors of the minor component were restrained to be nearly isotropic.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of FeCl2(C25H19N3) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.
[2,6-Bis(6-methylquinolin-2-yl)pyridine- κ3N,N',N'']dichloridoiron(II) top
Crystal data top
[FeCl2(C25H19N3)]Z = 2
Mr = 488.18F(000) = 500
Triclinic, P1Dx = 1.552 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.6228 (7) ÅCell parameters from 4559 reflections
b = 10.2558 (8) Åθ = 2.6–28.2°
c = 10.7324 (8) ŵ = 1.00 mm1
α = 94.352 (1)°T = 100 K
β = 95.481 (1)°Block, black
γ = 96.121 (1)°0.30 × 0.10 × 0.05 mm
V = 1044.35 (14) Å3
Data collection top
Bruker SMART APEX
diffractometer
4757 independent reflections
Radiation source: fine-focus sealed tube3954 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω scansθmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.754, Tmax = 0.952k = 1313
9910 measured reflectionsl = 1313
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0511P)2 + 1.0201P]
where P = (Fo2 + 2Fc2)/3
4757 reflections(Δ/σ)max = 0.001
292 parametersΔρmax = 0.54 e Å3
7 restraintsΔρmin = 0.44 e Å3
Crystal data top
[FeCl2(C25H19N3)]γ = 96.121 (1)°
Mr = 488.18V = 1044.35 (14) Å3
Triclinic, P1Z = 2
a = 9.6228 (7) ÅMo Kα radiation
b = 10.2558 (8) ŵ = 1.00 mm1
c = 10.7324 (8) ÅT = 100 K
α = 94.352 (1)°0.30 × 0.10 × 0.05 mm
β = 95.481 (1)°
Data collection top
Bruker SMART APEX
diffractometer
4757 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3954 reflections with I > 2σ(I)
Tmin = 0.754, Tmax = 0.952Rint = 0.024
9910 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0357 restraints
wR(F2) = 0.108H-atom parameters constrained
S = 1.05Δρmax = 0.54 e Å3
4757 reflectionsΔρmin = 0.44 e Å3
292 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Fe10.34748 (3)0.81412 (3)0.22283 (3)0.01918 (11)
Cl10.16748 (18)0.73795 (9)0.34366 (18)0.0225 (4)0.938 (11)
Cl1'0.211 (5)0.730 (2)0.377 (3)0.047 (6)0.062 (11)
Cl20.27672 (8)0.85227 (6)0.02182 (6)0.03212 (17)
N10.4298 (2)0.61956 (18)0.19090 (18)0.0185 (4)
N20.5602 (2)0.84553 (19)0.29589 (18)0.0188 (4)
N30.3828 (2)1.02324 (19)0.31020 (18)0.0185 (4)
C10.3563 (2)0.5061 (2)0.1319 (2)0.0197 (5)
C20.2114 (3)0.5039 (2)0.0943 (2)0.0236 (5)
H20.16560.58030.10970.028*
C30.1373 (3)0.3912 (2)0.0355 (2)0.0233 (5)
H30.03980.39100.01070.028*
C40.2005 (3)0.2747 (2)0.0101 (2)0.0214 (5)
C50.3407 (3)0.2756 (2)0.0458 (2)0.0218 (5)
H50.38460.19840.02890.026*
C60.4219 (3)0.3901 (2)0.1079 (2)0.0201 (5)
C70.1113 (3)0.1550 (2)0.0542 (2)0.0268 (5)
H7A0.17090.08550.07180.040*
H7B0.06370.17750.13330.040*
H7C0.04110.12390.00040.040*
C80.5659 (3)0.3955 (2)0.1470 (2)0.0251 (5)
H80.61360.32020.13270.030*
C90.6372 (3)0.5093 (3)0.2057 (2)0.0255 (5)
H90.73460.51330.23280.031*
C100.5660 (2)0.6202 (2)0.2256 (2)0.0187 (5)
C110.6408 (2)0.7465 (2)0.2875 (2)0.0183 (5)
C120.7816 (2)0.7639 (2)0.3330 (2)0.0209 (5)
H120.83770.69350.32540.025*
C130.8396 (3)0.8867 (2)0.3902 (2)0.0228 (5)
H130.93610.90090.42180.027*
C140.7556 (3)0.9881 (2)0.4005 (2)0.0224 (5)
H140.79321.07220.44010.027*
C150.6156 (2)0.9643 (2)0.3520 (2)0.0197 (5)
C160.5151 (3)1.0641 (2)0.3564 (2)0.0203 (5)
C170.5577 (3)1.1949 (3)0.4088 (3)0.0285 (6)
H170.65271.22140.44120.034*
C180.4599 (3)1.2824 (3)0.4121 (2)0.0281 (6)
H180.48761.37040.44660.034*
C190.3201 (3)1.2440 (2)0.3654 (2)0.0211 (5)
C200.2134 (3)1.3296 (2)0.3667 (2)0.0238 (5)
H200.23701.41860.39990.029*
C210.0778 (3)1.2866 (2)0.3213 (2)0.0259 (5)
C220.0444 (3)1.1538 (2)0.2698 (2)0.0249 (5)
H220.04951.12370.23640.030*
C230.1446 (3)1.0680 (2)0.2674 (2)0.0223 (5)
H230.11920.97930.23390.027*
C240.2846 (3)1.1113 (2)0.3143 (2)0.0199 (5)
C250.0365 (3)1.3765 (3)0.3212 (3)0.0342 (6)
H25A0.00591.46830.32880.051*
H25B0.09111.36110.39230.051*
H25C0.09851.35830.24250.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.01616 (18)0.01714 (17)0.02359 (19)0.00279 (12)0.00055 (13)0.00168 (13)
Cl10.0196 (5)0.0208 (4)0.0263 (6)0.0002 (3)0.0040 (4)0.0017 (3)
Cl1'0.046 (10)0.052 (8)0.042 (9)0.001 (7)0.013 (8)0.005 (6)
Cl20.0433 (4)0.0305 (3)0.0245 (3)0.0176 (3)0.0004 (3)0.0001 (2)
N10.0183 (10)0.0174 (9)0.0195 (10)0.0013 (7)0.0009 (8)0.0012 (7)
N20.0170 (9)0.0187 (9)0.0206 (10)0.0006 (7)0.0048 (8)0.0005 (7)
N30.0173 (10)0.0197 (9)0.0182 (9)0.0014 (8)0.0023 (7)0.0001 (7)
C10.0218 (12)0.0175 (10)0.0200 (11)0.0019 (9)0.0032 (9)0.0014 (9)
C20.0221 (12)0.0200 (11)0.0279 (13)0.0032 (9)0.0000 (10)0.0021 (9)
C30.0191 (12)0.0218 (11)0.0279 (13)0.0002 (9)0.0005 (10)0.0012 (10)
C40.0274 (13)0.0191 (11)0.0171 (11)0.0009 (9)0.0009 (9)0.0014 (9)
C50.0275 (13)0.0181 (11)0.0203 (12)0.0049 (9)0.0032 (10)0.0005 (9)
C60.0242 (12)0.0185 (11)0.0187 (11)0.0037 (9)0.0049 (9)0.0040 (9)
C70.0339 (14)0.0191 (11)0.0255 (13)0.0015 (10)0.0006 (11)0.0012 (9)
C80.0268 (13)0.0236 (12)0.0263 (13)0.0073 (10)0.0046 (10)0.0019 (10)
C90.0214 (12)0.0284 (13)0.0276 (13)0.0068 (10)0.0025 (10)0.0022 (10)
C100.0202 (11)0.0186 (11)0.0178 (11)0.0028 (9)0.0035 (9)0.0032 (9)
C110.0186 (11)0.0206 (11)0.0154 (11)0.0007 (9)0.0036 (9)0.0006 (9)
C120.0182 (11)0.0263 (12)0.0183 (11)0.0036 (9)0.0014 (9)0.0016 (9)
C130.0177 (11)0.0302 (12)0.0202 (12)0.0010 (10)0.0029 (9)0.0022 (10)
C140.0222 (12)0.0228 (11)0.0208 (12)0.0021 (9)0.0030 (9)0.0016 (9)
C150.0210 (12)0.0206 (11)0.0181 (11)0.0030 (9)0.0046 (9)0.0006 (9)
C160.0229 (12)0.0201 (11)0.0189 (11)0.0026 (9)0.0065 (9)0.0023 (9)
C170.0276 (13)0.0292 (13)0.0274 (13)0.0009 (11)0.0000 (11)0.0007 (10)
C180.0343 (15)0.0222 (12)0.0273 (13)0.0010 (11)0.0056 (11)0.0012 (10)
C190.0256 (12)0.0192 (11)0.0187 (11)0.0009 (9)0.0054 (9)0.0012 (9)
C200.0309 (13)0.0181 (11)0.0232 (12)0.0039 (10)0.0076 (10)0.0003 (9)
C210.0285 (13)0.0242 (12)0.0281 (13)0.0085 (10)0.0100 (10)0.0063 (10)
C220.0227 (12)0.0248 (12)0.0285 (13)0.0036 (10)0.0066 (10)0.0056 (10)
C230.0241 (12)0.0192 (11)0.0242 (12)0.0029 (9)0.0053 (10)0.0010 (9)
C240.0230 (12)0.0187 (11)0.0196 (11)0.0039 (9)0.0071 (9)0.0028 (9)
C250.0296 (14)0.0257 (13)0.0502 (18)0.0101 (11)0.0092 (13)0.0059 (12)
Geometric parameters (Å, º) top
Fe1—N12.2386 (19)C9—H90.9500
Fe1—N22.103 (2)C10—C111.488 (3)
Fe1—N32.2523 (19)C11—C121.384 (3)
Fe1—Cl12.3636 (8)C12—C131.393 (3)
Fe1—Cl1'2.369 (9)C12—H120.9500
Fe1—Cl22.2748 (7)C13—C141.388 (3)
N1—C101.328 (3)C13—H130.9500
N1—C11.372 (3)C14—C151.386 (3)
N2—C111.345 (3)C14—H140.9500
N2—C151.349 (3)C15—C161.483 (3)
N3—C161.333 (3)C16—C171.416 (3)
N3—C241.376 (3)C17—C181.369 (4)
C1—C21.411 (3)C17—H170.9500
C1—C61.423 (3)C18—C191.394 (4)
C2—C31.368 (3)C18—H180.9500
C2—H20.9500C19—C241.422 (3)
C3—C41.418 (3)C19—C201.420 (3)
C3—H30.9500C20—C211.363 (4)
C4—C51.365 (3)C20—H200.9500
C4—C71.501 (3)C21—C221.422 (4)
C5—C61.421 (3)C21—C251.508 (3)
C5—H50.9500C22—C231.373 (3)
C6—C81.403 (3)C22—H220.9500
C7—H7A0.9800C23—C241.406 (3)
C7—H7B0.9800C23—H230.9500
C7—H7C0.9800C25—H25A0.9800
C8—C91.365 (4)C25—H25B0.9800
C8—H80.9500C25—H25C0.9800
C9—C101.402 (3)
N2—Fe1—N174.57 (7)C10—C9—H9120.2
N2—Fe1—N374.29 (7)N1—C10—C9122.6 (2)
N1—Fe1—N3148.58 (7)N1—C10—C11116.18 (19)
N2—Fe1—Cl2121.77 (6)C9—C10—C11121.2 (2)
N1—Fe1—Cl2100.57 (5)N2—C11—C12121.4 (2)
N3—Fe1—Cl299.20 (5)N2—C11—C10114.5 (2)
N2—Fe1—Cl1122.35 (8)C12—C11—C10124.1 (2)
N1—Fe1—Cl195.84 (6)C11—C12—C13118.8 (2)
N3—Fe1—Cl197.19 (6)C11—C12—H12120.6
Cl2—Fe1—Cl1115.88 (6)C13—C12—H12120.6
N2—Fe1—Cl1'109.4 (15)C14—C13—C12119.6 (2)
N1—Fe1—Cl1'90.5 (9)C14—C13—H13120.2
N3—Fe1—Cl1'95.9 (5)C12—C13—H13120.2
Cl2—Fe1—Cl1'128.8 (15)C15—C14—C13118.6 (2)
Cl1—Fe1—Cl1'13.1 (14)C15—C14—H14120.7
C10—N1—C1118.53 (19)C13—C14—H14120.7
C10—N1—Fe1114.81 (15)N2—C15—C14121.5 (2)
C1—N1—Fe1126.46 (15)N2—C15—C16114.5 (2)
C11—N2—C15120.0 (2)C14—C15—C16124.0 (2)
C11—N2—Fe1119.82 (16)N3—C16—C17122.2 (2)
C15—N2—Fe1120.19 (15)N3—C16—C15116.2 (2)
C16—N3—C24118.6 (2)C17—C16—C15121.5 (2)
C16—N3—Fe1114.61 (15)C18—C17—C16119.0 (2)
C24—N3—Fe1126.69 (15)C18—C17—H17120.5
N1—C1—C2119.2 (2)C16—C17—H17120.5
N1—C1—C6121.8 (2)C17—C18—C19120.9 (2)
C2—C1—C6119.0 (2)C17—C18—H18119.6
C3—C2—C1119.6 (2)C19—C18—H18119.6
C3—C2—H2120.2C18—C19—C24117.1 (2)
C1—C2—H2120.2C18—C19—C20123.7 (2)
C2—C3—C4122.5 (2)C24—C19—C20119.2 (2)
C2—C3—H3118.8C21—C20—C19121.3 (2)
C4—C3—H3118.8C21—C20—H20119.3
C5—C4—C3118.5 (2)C19—C20—H20119.3
C5—C4—C7122.5 (2)C20—C21—C22118.7 (2)
C3—C4—C7119.0 (2)C20—C21—C25122.0 (2)
C4—C5—C6121.1 (2)C22—C21—C25119.3 (2)
C4—C5—H5119.4C23—C22—C21121.6 (2)
C6—C5—H5119.4C23—C22—H22119.2
C8—C6—C5123.2 (2)C21—C22—H22119.2
C8—C6—C1117.5 (2)C22—C23—C24120.1 (2)
C5—C6—C1119.4 (2)C22—C23—H23120.0
C4—C7—H7A109.5C24—C23—H23120.0
C4—C7—H7B109.5N3—C24—C23118.8 (2)
H7A—C7—H7B109.5N3—C24—C19122.2 (2)
C4—C7—H7C109.5C23—C24—C19119.0 (2)
H7A—C7—H7C109.5C21—C25—H25A109.5
H7B—C7—H7C109.5C21—C25—H25B109.5
C9—C8—C6119.8 (2)H25A—C25—H25B109.5
C9—C8—H8120.1C21—C25—H25C109.5
C6—C8—H8120.1H25A—C25—H25C109.5
C8—C9—C10119.7 (2)H25B—C25—H25C109.5
C8—C9—H9120.2
N2—Fe1—N1—C103.07 (16)C1—N1—C10—C11179.1 (2)
N3—Fe1—N1—C1010.9 (2)Fe1—N1—C10—C113.8 (3)
Cl2—Fe1—N1—C10117.20 (16)C8—C9—C10—N10.8 (4)
Cl1—Fe1—N1—C10125.06 (17)C8—C9—C10—C11179.1 (2)
Cl1'—Fe1—N1—C10113.1 (13)C15—N2—C11—C121.4 (3)
N2—Fe1—N1—C1177.9 (2)Fe1—N2—C11—C12179.14 (17)
N3—Fe1—N1—C1174.20 (17)C15—N2—C11—C10178.9 (2)
Cl2—Fe1—N1—C157.66 (19)Fe1—N2—C11—C100.5 (3)
Cl1—Fe1—N1—C160.08 (19)N1—C10—C11—N22.3 (3)
Cl1'—Fe1—N1—C172.0 (13)C9—C10—C11—N2177.5 (2)
N1—Fe1—N2—C111.86 (17)N1—C10—C11—C12178.0 (2)
N3—Fe1—N2—C11177.61 (19)C9—C10—C11—C122.1 (4)
Cl2—Fe1—N2—C1191.17 (17)N2—C11—C12—C130.9 (3)
Cl1—Fe1—N2—C1189.00 (17)C10—C11—C12—C13179.5 (2)
Cl1'—Fe1—N2—C1186.8 (7)C11—C12—C13—C140.2 (4)
N1—Fe1—N2—C15177.57 (19)C12—C13—C14—C150.7 (4)
N3—Fe1—N2—C151.81 (17)C11—N2—C15—C140.9 (3)
Cl2—Fe1—N2—C1589.40 (18)Fe1—N2—C15—C14179.70 (18)
Cl1—Fe1—N2—C1590.42 (18)C11—N2—C15—C16179.2 (2)
Cl1'—Fe1—N2—C1592.6 (7)Fe1—N2—C15—C160.2 (3)
N2—Fe1—N3—C163.33 (16)C13—C14—C15—N20.2 (4)
N1—Fe1—N3—C1611.2 (2)C13—C14—C15—C16179.7 (2)
Cl2—Fe1—N3—C16117.23 (16)C24—N3—C16—C170.3 (3)
Cl1—Fe1—N3—C16124.98 (17)Fe1—N3—C16—C17176.64 (19)
Cl1'—Fe1—N3—C16111.9 (15)C24—N3—C16—C15178.7 (2)
N2—Fe1—N3—C24180.0 (2)Fe1—N3—C16—C154.3 (3)
N1—Fe1—N3—C24172.12 (17)N2—C15—C16—N32.9 (3)
Cl2—Fe1—N3—C2459.44 (19)C14—C15—C16—N3177.2 (2)
Cl1—Fe1—N3—C2458.34 (19)N2—C15—C16—C17178.1 (2)
Cl1'—Fe1—N3—C2471.4 (15)C14—C15—C16—C171.8 (4)
C10—N1—C1—C2180.0 (2)N3—C16—C17—C180.1 (4)
Fe1—N1—C1—C25.3 (3)C15—C16—C17—C18179.0 (2)
C10—N1—C1—C60.4 (3)C16—C17—C18—C190.4 (4)
Fe1—N1—C1—C6175.07 (17)C17—C18—C19—C240.3 (4)
N1—C1—C2—C3179.9 (2)C17—C18—C19—C20179.6 (2)
C6—C1—C2—C30.3 (4)C18—C19—C20—C21179.2 (2)
C1—C2—C3—C40.0 (4)C24—C19—C20—C210.7 (4)
C2—C3—C4—C50.1 (4)C19—C20—C21—C221.1 (4)
C2—C3—C4—C7179.7 (2)C19—C20—C21—C25179.6 (2)
C3—C4—C5—C60.5 (4)C20—C21—C22—C231.3 (4)
C7—C4—C5—C6179.3 (2)C25—C21—C22—C23179.9 (2)
C4—C5—C6—C8179.6 (2)C21—C22—C23—C241.2 (4)
C4—C5—C6—C10.7 (4)C16—N3—C24—C23179.1 (2)
N1—C1—C6—C80.0 (4)Fe1—N3—C24—C234.4 (3)
C2—C1—C6—C8179.7 (2)C16—N3—C24—C190.4 (3)
N1—C1—C6—C5179.7 (2)Fe1—N3—C24—C19176.16 (17)
C2—C1—C6—C50.6 (3)C22—C23—C24—N3179.8 (2)
C5—C6—C8—C9179.7 (2)C22—C23—C24—C190.8 (4)
C1—C6—C8—C90.1 (4)C18—C19—C24—N30.1 (4)
C6—C8—C9—C100.4 (4)C20—C19—C24—N3180.0 (2)
C1—N1—C10—C90.7 (3)C18—C19—C24—C23179.4 (2)
Fe1—N1—C10—C9176.04 (19)C20—C19—C24—C230.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···Cl2i0.952.703.561 (2)151
C17—H17···Cl1ii0.952.733.538 (4)144
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+2, z+1.

Experimental details

Crystal data
Chemical formula[FeCl2(C25H19N3)]
Mr488.18
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)9.6228 (7), 10.2558 (8), 10.7324 (8)
α, β, γ (°)94.352 (1), 95.481 (1), 96.121 (1)
V3)1044.35 (14)
Z2
Radiation typeMo Kα
µ (mm1)1.00
Crystal size (mm)0.30 × 0.10 × 0.05
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.754, 0.952
No. of measured, independent and
observed [I > 2σ(I)] reflections
9910, 4757, 3954
Rint0.024
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.108, 1.05
No. of reflections4757
No. of parameters292
No. of restraints7
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.54, 0.44

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top
Fe1—N12.2386 (19)Fe1—Cl12.3636 (8)
Fe1—N22.103 (2)Fe1—Cl22.2748 (7)
Fe1—N32.2523 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···Cl2i0.952.703.561 (2)151
C17—H17···Cl1ii0.952.733.538 (4)144
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+2, z+1.
 

Acknowledgements

We thank the Graduate Experimental Research Fund of Northwest University (project No. 09YSY22), the National Natural Science Foundation of China (No.20971104) and the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBuu-Hoi, N. P., Perin, F. & Jacquignon, P. (1965). J. Heterocycl. Chem. 2, 7–10.  CrossRef CAS Google Scholar
First citationLi, X.-P., Liu, Y.-Y. & Zhao, J.-S. (2010). Acta Cryst. E66, m1215.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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