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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): m1299.
Published online 2010 September 25. doi:  10.1107/S1600536810037049
PMCID: PMC2983294

[2,6-Bis(6-methyl­quinolin-2-yl)pyridine-κ3 N,N′,N′′]dichloridoiron(II)

Abstract

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 [triangle]). For a related structure, see: Li et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1299-scheme1.jpg

Experimental

Crystal data

  • [FeCl2(C25H19N3)]
  • M r = 488.18
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1299-efi1.jpg
  • 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 [triangle]) T min = 0.754, T max = 0.952
  • 9910 measured reflections
  • 4757 independent reflections
  • 3954 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 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

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810037049/xu5032sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037049/xu5032Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Comment

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).

Experimental

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

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.

Figures

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.

Crystal data

[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

Bruker SMART APEX diffractometer4757 independent reflections
Radiation source: fine-focus sealed tube3954 reflections with I > 2σ(I)
graphiteRint = 0.024
ω scansθmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.754, Tmax = 0.952k = −13→13
9910 measured reflectionsl = −13→13

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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 1.05w = 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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)
H7A0.17090.0855−0.07180.040*
H7B0.06370.1775−0.13330.040*
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)
H22−0.04951.12370.23640.030*
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)
C25−0.0365 (3)1.3765 (3)0.3212 (3)0.0342 (6)
H25A0.00591.46830.32880.051*
H25B−0.09111.36110.39230.051*
H25C−0.09851.35830.24250.051*

Atomic displacement parameters (Å2)

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, °)

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—C10−3.07 (16)C1—N1—C10—C11179.1 (2)
N3—Fe1—N1—C10−10.9 (2)Fe1—N1—C10—C113.8 (3)
Cl2—Fe1—N1—C10117.20 (16)C8—C9—C10—N10.8 (4)
Cl1—Fe1—N1—C10−125.06 (17)C8—C9—C10—C11−179.1 (2)
Cl1'—Fe1—N1—C10−113.1 (13)C15—N2—C11—C12−1.4 (3)
N2—Fe1—N1—C1−177.9 (2)Fe1—N2—C11—C12179.14 (17)
N3—Fe1—N1—C1174.20 (17)C15—N2—C11—C10178.9 (2)
Cl2—Fe1—N1—C1−57.66 (19)Fe1—N2—C11—C10−0.5 (3)
Cl1—Fe1—N1—C160.08 (19)N1—C10—C11—N2−2.3 (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—C12−2.1 (4)
Cl2—Fe1—N2—C11−91.17 (17)N2—C11—C12—C130.9 (3)
Cl1—Fe1—N2—C1189.00 (17)C10—C11—C12—C13−179.5 (2)
Cl1'—Fe1—N2—C1186.8 (7)C11—C12—C13—C140.2 (4)
N1—Fe1—N2—C15−177.57 (19)C12—C13—C14—C15−0.7 (4)
N3—Fe1—N2—C15−1.81 (17)C11—N2—C15—C140.9 (3)
Cl2—Fe1—N2—C1589.40 (18)Fe1—N2—C15—C14−179.70 (18)
Cl1—Fe1—N2—C15−90.42 (18)C11—N2—C15—C16−179.2 (2)
Cl1'—Fe1—N2—C15−92.6 (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—C16−179.7 (2)
Cl2—Fe1—N3—C16−117.23 (16)C24—N3—C16—C17−0.3 (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—C24−180.0 (2)Fe1—N3—C16—C15−4.3 (3)
N1—Fe1—N3—C24−172.12 (17)N2—C15—C16—N32.9 (3)
Cl2—Fe1—N3—C2459.44 (19)C14—C15—C16—N3−177.2 (2)
Cl1—Fe1—N3—C24−58.34 (19)N2—C15—C16—C17−178.1 (2)
Cl1'—Fe1—N3—C24−71.4 (15)C14—C15—C16—C171.8 (4)
C10—N1—C1—C2−180.0 (2)N3—C16—C17—C18−0.1 (4)
Fe1—N1—C1—C2−5.3 (3)C15—C16—C17—C18−179.0 (2)
C10—N1—C1—C60.4 (3)C16—C17—C18—C190.4 (4)
Fe1—N1—C1—C6175.07 (17)C17—C18—C19—C24−0.3 (4)
N1—C1—C2—C3−179.9 (2)C17—C18—C19—C20179.6 (2)
C6—C1—C2—C3−0.3 (4)C18—C19—C20—C21−179.2 (2)
C1—C2—C3—C40.0 (4)C24—C19—C20—C210.7 (4)
C2—C3—C4—C5−0.1 (4)C19—C20—C21—C22−1.1 (4)
C2—C3—C4—C7179.7 (2)C19—C20—C21—C25−179.6 (2)
C3—C4—C5—C60.5 (4)C20—C21—C22—C231.3 (4)
C7—C4—C5—C6−179.3 (2)C25—C21—C22—C23179.9 (2)
C4—C5—C6—C8179.6 (2)C21—C22—C23—C24−1.2 (4)
C4—C5—C6—C1−0.7 (4)C16—N3—C24—C23−179.1 (2)
N1—C1—C6—C80.0 (4)Fe1—N3—C24—C234.4 (3)
C2—C1—C6—C8−179.7 (2)C16—N3—C24—C190.4 (3)
N1—C1—C6—C5−179.7 (2)Fe1—N3—C24—C19−176.16 (17)
C2—C1—C6—C50.6 (3)C22—C23—C24—N3−179.8 (2)
C5—C6—C8—C9179.7 (2)C22—C23—C24—C190.8 (4)
C1—C6—C8—C90.1 (4)C18—C19—C24—N3−0.1 (4)
C6—C8—C9—C10−0.4 (4)C20—C19—C24—N3−180.0 (2)
C1—N1—C10—C9−0.7 (3)C18—C19—C24—C23179.4 (2)
Fe1—N1—C10—C9−176.04 (19)C20—C19—C24—C23−0.5 (3)

Hydrogen-bond geometry (Å, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5032).

References

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