Literature DB >> 21587438

[2,6-Bis(6-methyl-quinolin-2-yl)pyridine-κN,N',N'']dichloridoiron(II).

Xiao-Ping Li, Jian-She Zhao, Seik Weng Ng.   

Abstract

In the mol-ecule of the title compound, [FeCl(2)(C(25)H(19)N(3))], the three N atoms span the axial-equatorial-axial sites of the trigonal-bipyramidal coordination polyhedron; the geometry of the Fe(II) 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. Inter-molecular C-H⋯Cl hydrogen bonding occurs in the crystal structure.

Entities:  

Year:  2010        PMID: 21587438      PMCID: PMC2983294          DOI: 10.1107/S1600536810037049

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

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

Experimental

Crystal data

[FeCl2(C25H19N3)] M = 488.18 Triclinic, 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 ▶) 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 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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 ▶). 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
[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
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 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
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*
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)
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)
D—H···AD—HH···AD···AD—H···A
C8—H8···Cl2i0.952.703.561 (2)151
C17—H17···Cl1ii0.952.733.538 (4)144
Table 1

Selected bond lengths (Å)

Fe1—N12.2386 (19)
Fe1—N22.103 (2)
Fe1—N32.2523 (19)
Fe1—Cl12.3636 (8)
Fe1—Cl22.2748 (7)
Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—H⋯A
C8—H8⋯Cl2i0.952.703.561 (2)151
C17—H17⋯Cl1ii0.952.733.538 (4)144

Symmetry codes: (i) ; (ii) .

  2 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  {2,6-Bis[(4-bromo-phen-yl)imino-meth-yl]pyridine-κN,N',N''}trichlorido-chromium(III).

Authors:  Xiao-Ping Li; Yong-Yong Liu; Jian-She Zhao
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-09-08
  2 in total

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