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

Li, X.-P.; Zhao, J.-S.; Ng, S.W.

doi:10.1107/S1600536810037049

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page m1299

doi:10.1107/S1600536810037049

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

Xiao-Ping Li,^a Jian-She Zhao ^a and Seik Weng Ng ^b ^*

^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 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. 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 ). For a related structure, see: Li et al. (2010 ).

Experimental

Crystal data

[FeCl₂(C₂₅H₁₉N₃)]
M_r = 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 ) 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[F² > 2σ(F²)] = 0.035
wR(F²) = 0.108
S = 1.05
4757 reflections
292 parameters
7 restraints
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −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	D⋯A	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 ); 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 ).

Supporting information

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

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

checkCIF report

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.

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

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
M_r = 488.18	F(000) = 500
Triclinic, P1	D_x = 1.552 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6228 (7) Å	Cell parameters from 4559 reflections
b = 10.2558 (8) Å	θ = 2.6–28.2°
c = 10.7324 (8) Å	µ = 1.00 mm⁻¹
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 tube	3954 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.754, T_max = 0.952	k = −13→13
9910 measured reflections	l = −13→13

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0511P)² + 1.0201P] where P = (F_o² + 2F_c²)/3
4757 reflections	(Δ/σ)_max = 0.001
292 parameters	Δρ_max = 0.54 e Å⁻³
7 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

[FeCl₂(C₂₅H₁₉N₃)]	γ = 96.121 (1)°
M_r = 488.18	V = 1044.35 (14) Å³
Triclinic, P1	Z = 2
a = 9.6228 (7) Å	Mo Kα radiation
b = 10.2558 (8) Å	µ = 1.00 mm⁻¹
c = 10.7324 (8) Å	T = 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)
T_min = 0.754, T_max = 0.952	R_int = 0.024
9910 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	7 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.05	Δρ_max = 0.54 e Å⁻³
4757 reflections	Δρ_min = −0.44 e Å⁻³
292 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Fe1	0.34748 (3)	0.81412 (3)	0.22283 (3)	0.01918 (11)
Cl1	0.16748 (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)
Cl2	0.27672 (8)	0.85227 (6)	0.02182 (6)	0.03212 (17)
N1	0.4298 (2)	0.61956 (18)	0.19090 (18)	0.0185 (4)
N2	0.5602 (2)	0.84553 (19)	0.29589 (18)	0.0188 (4)
N3	0.3828 (2)	1.02324 (19)	0.31020 (18)	0.0185 (4)
C1	0.3563 (2)	0.5061 (2)	0.1319 (2)	0.0197 (5)
C2	0.2114 (3)	0.5039 (2)	0.0943 (2)	0.0236 (5)
H2	0.1656	0.5803	0.1097	0.028*
C3	0.1373 (3)	0.3912 (2)	0.0355 (2)	0.0233 (5)
H3	0.0398	0.3910	0.0107	0.028*
C4	0.2005 (3)	0.2747 (2)	0.0101 (2)	0.0214 (5)
C5	0.3407 (3)	0.2756 (2)	0.0458 (2)	0.0218 (5)
H5	0.3846	0.1984	0.0289	0.026*
C6	0.4219 (3)	0.3901 (2)	0.1079 (2)	0.0201 (5)
C7	0.1113 (3)	0.1550 (2)	−0.0542 (2)	0.0268 (5)
H7A	0.1709	0.0855	−0.0718	0.040*
H7B	0.0637	0.1775	−0.1333	0.040*
H7C	0.0411	0.1239	0.0004	0.040*
C8	0.5659 (3)	0.3955 (2)	0.1470 (2)	0.0251 (5)
H8	0.6136	0.3202	0.1327	0.030*
C9	0.6372 (3)	0.5093 (3)	0.2057 (2)	0.0255 (5)
H9	0.7346	0.5133	0.2328	0.031*
C10	0.5660 (2)	0.6202 (2)	0.2256 (2)	0.0187 (5)
C11	0.6408 (2)	0.7465 (2)	0.2875 (2)	0.0183 (5)
C12	0.7816 (2)	0.7639 (2)	0.3330 (2)	0.0209 (5)
H12	0.8377	0.6935	0.3254	0.025*
C13	0.8396 (3)	0.8867 (2)	0.3902 (2)	0.0228 (5)
H13	0.9361	0.9009	0.4218	0.027*
C14	0.7556 (3)	0.9881 (2)	0.4005 (2)	0.0224 (5)
H14	0.7932	1.0722	0.4401	0.027*
C15	0.6156 (2)	0.9643 (2)	0.3520 (2)	0.0197 (5)
C16	0.5151 (3)	1.0641 (2)	0.3564 (2)	0.0203 (5)
C17	0.5577 (3)	1.1949 (3)	0.4088 (3)	0.0285 (6)
H17	0.6527	1.2214	0.4412	0.034*
C18	0.4599 (3)	1.2824 (3)	0.4121 (2)	0.0281 (6)
H18	0.4876	1.3704	0.4466	0.034*
C19	0.3201 (3)	1.2440 (2)	0.3654 (2)	0.0211 (5)
C20	0.2134 (3)	1.3296 (2)	0.3667 (2)	0.0238 (5)
H20	0.2370	1.4186	0.3999	0.029*
C21	0.0778 (3)	1.2866 (2)	0.3213 (2)	0.0259 (5)
C22	0.0444 (3)	1.1538 (2)	0.2698 (2)	0.0249 (5)
H22	−0.0495	1.1237	0.2364	0.030*
C23	0.1446 (3)	1.0680 (2)	0.2674 (2)	0.0223 (5)
H23	0.1192	0.9793	0.2339	0.027*
C24	0.2846 (3)	1.1113 (2)	0.3143 (2)	0.0199 (5)
C25	−0.0365 (3)	1.3765 (3)	0.3212 (3)	0.0342 (6)
H25A	0.0059	1.4683	0.3288	0.051*
H25B	−0.0911	1.3611	0.3923	0.051*
H25C	−0.0985	1.3583	0.2425	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.01616 (18)	0.01714 (17)	0.02359 (19)	0.00279 (12)	0.00055 (13)	−0.00168 (13)
Cl1	0.0196 (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)
Cl2	0.0433 (4)	0.0305 (3)	0.0245 (3)	0.0176 (3)	0.0004 (3)	−0.0001 (2)
N1	0.0183 (10)	0.0174 (9)	0.0195 (10)	0.0013 (7)	0.0009 (8)	0.0012 (7)
N2	0.0170 (9)	0.0187 (9)	0.0206 (10)	0.0006 (7)	0.0048 (8)	0.0005 (7)
N3	0.0173 (10)	0.0197 (9)	0.0182 (9)	0.0014 (8)	0.0023 (7)	0.0001 (7)
C1	0.0218 (12)	0.0175 (10)	0.0200 (11)	0.0019 (9)	0.0032 (9)	0.0014 (9)
C2	0.0221 (12)	0.0200 (11)	0.0279 (13)	0.0032 (9)	0.0000 (10)	−0.0021 (9)
C3	0.0191 (12)	0.0218 (11)	0.0279 (13)	0.0002 (9)	0.0005 (10)	0.0012 (10)
C4	0.0274 (13)	0.0191 (11)	0.0171 (11)	0.0009 (9)	0.0009 (9)	0.0014 (9)
C5	0.0275 (13)	0.0181 (11)	0.0203 (12)	0.0049 (9)	0.0032 (10)	0.0005 (9)
C6	0.0242 (12)	0.0185 (11)	0.0187 (11)	0.0037 (9)	0.0049 (9)	0.0040 (9)
C7	0.0339 (14)	0.0191 (11)	0.0255 (13)	−0.0015 (10)	0.0006 (11)	−0.0012 (9)
C8	0.0268 (13)	0.0236 (12)	0.0263 (13)	0.0073 (10)	0.0046 (10)	0.0019 (10)
C9	0.0214 (12)	0.0284 (13)	0.0276 (13)	0.0068 (10)	0.0025 (10)	0.0022 (10)
C10	0.0202 (11)	0.0186 (11)	0.0178 (11)	0.0028 (9)	0.0035 (9)	0.0032 (9)
C11	0.0186 (11)	0.0206 (11)	0.0154 (11)	0.0007 (9)	0.0036 (9)	0.0006 (9)
C12	0.0182 (11)	0.0263 (12)	0.0183 (11)	0.0036 (9)	0.0014 (9)	0.0016 (9)
C13	0.0177 (11)	0.0302 (12)	0.0202 (12)	0.0010 (10)	0.0029 (9)	0.0022 (10)
C14	0.0222 (12)	0.0228 (11)	0.0208 (12)	−0.0021 (9)	0.0030 (9)	−0.0016 (9)
C15	0.0210 (12)	0.0206 (11)	0.0181 (11)	0.0030 (9)	0.0046 (9)	0.0006 (9)
C16	0.0229 (12)	0.0201 (11)	0.0189 (11)	0.0026 (9)	0.0065 (9)	0.0023 (9)
C17	0.0276 (13)	0.0292 (13)	0.0274 (13)	0.0009 (11)	0.0000 (11)	0.0007 (10)
C18	0.0343 (15)	0.0222 (12)	0.0273 (13)	−0.0010 (11)	0.0056 (11)	0.0012 (10)
C19	0.0256 (12)	0.0192 (11)	0.0187 (11)	0.0009 (9)	0.0054 (9)	0.0012 (9)
C20	0.0309 (13)	0.0181 (11)	0.0232 (12)	0.0039 (10)	0.0076 (10)	0.0003 (9)
C21	0.0285 (13)	0.0242 (12)	0.0281 (13)	0.0085 (10)	0.0100 (10)	0.0063 (10)
C22	0.0227 (12)	0.0248 (12)	0.0285 (13)	0.0036 (10)	0.0066 (10)	0.0056 (10)
C23	0.0241 (12)	0.0192 (11)	0.0242 (12)	0.0029 (9)	0.0053 (10)	0.0010 (9)
C24	0.0230 (12)	0.0187 (11)	0.0196 (11)	0.0039 (9)	0.0071 (9)	0.0028 (9)
C25	0.0296 (14)	0.0257 (13)	0.0502 (18)	0.0101 (11)	0.0092 (13)	0.0059 (12)

Geometric parameters (Å, º) top

Fe1—N1	2.2386 (19)	C9—H9	0.9500
Fe1—N2	2.103 (2)	C10—C11	1.488 (3)
Fe1—N3	2.2523 (19)	C11—C12	1.384 (3)
Fe1—Cl1	2.3636 (8)	C12—C13	1.393 (3)
Fe1—Cl1'	2.369 (9)	C12—H12	0.9500
Fe1—Cl2	2.2748 (7)	C13—C14	1.388 (3)
N1—C10	1.328 (3)	C13—H13	0.9500
N1—C1	1.372 (3)	C14—C15	1.386 (3)
N2—C11	1.345 (3)	C14—H14	0.9500
N2—C15	1.349 (3)	C15—C16	1.483 (3)
N3—C16	1.333 (3)	C16—C17	1.416 (3)
N3—C24	1.376 (3)	C17—C18	1.369 (4)
C1—C2	1.411 (3)	C17—H17	0.9500
C1—C6	1.423 (3)	C18—C19	1.394 (4)
C2—C3	1.368 (3)	C18—H18	0.9500
C2—H2	0.9500	C19—C24	1.422 (3)
C3—C4	1.418 (3)	C19—C20	1.420 (3)
C3—H3	0.9500	C20—C21	1.363 (4)
C4—C5	1.365 (3)	C20—H20	0.9500
C4—C7	1.501 (3)	C21—C22	1.422 (4)
C5—C6	1.421 (3)	C21—C25	1.508 (3)
C5—H5	0.9500	C22—C23	1.373 (3)
C6—C8	1.403 (3)	C22—H22	0.9500
C7—H7A	0.9800	C23—C24	1.406 (3)
C7—H7B	0.9800	C23—H23	0.9500
C7—H7C	0.9800	C25—H25A	0.9800
C8—C9	1.365 (4)	C25—H25B	0.9800
C8—H8	0.9500	C25—H25C	0.9800
C9—C10	1.402 (3)

N2—Fe1—N1	74.57 (7)	C10—C9—H9	120.2
N2—Fe1—N3	74.29 (7)	N1—C10—C9	122.6 (2)
N1—Fe1—N3	148.58 (7)	N1—C10—C11	116.18 (19)
N2—Fe1—Cl2	121.77 (6)	C9—C10—C11	121.2 (2)
N1—Fe1—Cl2	100.57 (5)	N2—C11—C12	121.4 (2)
N3—Fe1—Cl2	99.20 (5)	N2—C11—C10	114.5 (2)
N2—Fe1—Cl1	122.35 (8)	C12—C11—C10	124.1 (2)
N1—Fe1—Cl1	95.84 (6)	C11—C12—C13	118.8 (2)
N3—Fe1—Cl1	97.19 (6)	C11—C12—H12	120.6
Cl2—Fe1—Cl1	115.88 (6)	C13—C12—H12	120.6
N2—Fe1—Cl1'	109.4 (15)	C14—C13—C12	119.6 (2)
N1—Fe1—Cl1'	90.5 (9)	C14—C13—H13	120.2
N3—Fe1—Cl1'	95.9 (5)	C12—C13—H13	120.2
Cl2—Fe1—Cl1'	128.8 (15)	C15—C14—C13	118.6 (2)
Cl1—Fe1—Cl1'	13.1 (14)	C15—C14—H14	120.7
C10—N1—C1	118.53 (19)	C13—C14—H14	120.7
C10—N1—Fe1	114.81 (15)	N2—C15—C14	121.5 (2)
C1—N1—Fe1	126.46 (15)	N2—C15—C16	114.5 (2)
C11—N2—C15	120.0 (2)	C14—C15—C16	124.0 (2)
C11—N2—Fe1	119.82 (16)	N3—C16—C17	122.2 (2)
C15—N2—Fe1	120.19 (15)	N3—C16—C15	116.2 (2)
C16—N3—C24	118.6 (2)	C17—C16—C15	121.5 (2)
C16—N3—Fe1	114.61 (15)	C18—C17—C16	119.0 (2)
C24—N3—Fe1	126.69 (15)	C18—C17—H17	120.5
N1—C1—C2	119.2 (2)	C16—C17—H17	120.5
N1—C1—C6	121.8 (2)	C17—C18—C19	120.9 (2)
C2—C1—C6	119.0 (2)	C17—C18—H18	119.6
C3—C2—C1	119.6 (2)	C19—C18—H18	119.6
C3—C2—H2	120.2	C18—C19—C24	117.1 (2)
C1—C2—H2	120.2	C18—C19—C20	123.7 (2)
C2—C3—C4	122.5 (2)	C24—C19—C20	119.2 (2)
C2—C3—H3	118.8	C21—C20—C19	121.3 (2)
C4—C3—H3	118.8	C21—C20—H20	119.3
C5—C4—C3	118.5 (2)	C19—C20—H20	119.3
C5—C4—C7	122.5 (2)	C20—C21—C22	118.7 (2)
C3—C4—C7	119.0 (2)	C20—C21—C25	122.0 (2)
C4—C5—C6	121.1 (2)	C22—C21—C25	119.3 (2)
C4—C5—H5	119.4	C23—C22—C21	121.6 (2)
C6—C5—H5	119.4	C23—C22—H22	119.2
C8—C6—C5	123.2 (2)	C21—C22—H22	119.2
C8—C6—C1	117.5 (2)	C22—C23—C24	120.1 (2)
C5—C6—C1	119.4 (2)	C22—C23—H23	120.0
C4—C7—H7A	109.5	C24—C23—H23	120.0
C4—C7—H7B	109.5	N3—C24—C23	118.8 (2)
H7A—C7—H7B	109.5	N3—C24—C19	122.2 (2)
C4—C7—H7C	109.5	C23—C24—C19	119.0 (2)
H7A—C7—H7C	109.5	C21—C25—H25A	109.5
H7B—C7—H7C	109.5	C21—C25—H25B	109.5
C9—C8—C6	119.8 (2)	H25A—C25—H25B	109.5
C9—C8—H8	120.1	C21—C25—H25C	109.5
C6—C8—H8	120.1	H25A—C25—H25C	109.5
C8—C9—C10	119.7 (2)	H25B—C25—H25C	109.5
C8—C9—H9	120.2

N2—Fe1—N1—C10	−3.07 (16)	C1—N1—C10—C11	179.1 (2)
N3—Fe1—N1—C10	−10.9 (2)	Fe1—N1—C10—C11	3.8 (3)
Cl2—Fe1—N1—C10	117.20 (16)	C8—C9—C10—N1	0.8 (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—C12	179.14 (17)
N3—Fe1—N1—C1	174.20 (17)	C15—N2—C11—C10	178.9 (2)
Cl2—Fe1—N1—C1	−57.66 (19)	Fe1—N2—C11—C10	−0.5 (3)
Cl1—Fe1—N1—C1	60.08 (19)	N1—C10—C11—N2	−2.3 (3)
Cl1'—Fe1—N1—C1	72.0 (13)	C9—C10—C11—N2	177.5 (2)
N1—Fe1—N2—C11	1.86 (17)	N1—C10—C11—C12	178.0 (2)
N3—Fe1—N2—C11	177.61 (19)	C9—C10—C11—C12	−2.1 (4)
Cl2—Fe1—N2—C11	−91.17 (17)	N2—C11—C12—C13	0.9 (3)
Cl1—Fe1—N2—C11	89.00 (17)	C10—C11—C12—C13	−179.5 (2)
Cl1'—Fe1—N2—C11	86.8 (7)	C11—C12—C13—C14	0.2 (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—C14	0.9 (3)
Cl2—Fe1—N2—C15	89.40 (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—C16	0.2 (3)
N2—Fe1—N3—C16	3.33 (16)	C13—C14—C15—N2	0.2 (4)
N1—Fe1—N3—C16	11.2 (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—C16	124.98 (17)	Fe1—N3—C16—C17	176.64 (19)
Cl1'—Fe1—N3—C16	111.9 (15)	C24—N3—C16—C15	178.7 (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—N3	2.9 (3)
Cl2—Fe1—N3—C24	59.44 (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—C17	1.8 (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—C6	0.4 (3)	C16—C17—C18—C19	0.4 (4)
Fe1—N1—C1—C6	175.07 (17)	C17—C18—C19—C24	−0.3 (4)
N1—C1—C2—C3	−179.9 (2)	C17—C18—C19—C20	179.6 (2)
C6—C1—C2—C3	−0.3 (4)	C18—C19—C20—C21	−179.2 (2)
C1—C2—C3—C4	0.0 (4)	C24—C19—C20—C21	0.7 (4)
C2—C3—C4—C5	−0.1 (4)	C19—C20—C21—C22	−1.1 (4)
C2—C3—C4—C7	179.7 (2)	C19—C20—C21—C25	−179.6 (2)
C3—C4—C5—C6	0.5 (4)	C20—C21—C22—C23	1.3 (4)
C7—C4—C5—C6	−179.3 (2)	C25—C21—C22—C23	179.9 (2)
C4—C5—C6—C8	179.6 (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—C8	0.0 (4)	Fe1—N3—C24—C23	4.4 (3)
C2—C1—C6—C8	−179.7 (2)	C16—N3—C24—C19	0.4 (3)
N1—C1—C6—C5	−179.7 (2)	Fe1—N3—C24—C19	−176.16 (17)
C2—C1—C6—C5	0.6 (3)	C22—C23—C24—N3	−179.8 (2)
C5—C6—C8—C9	179.7 (2)	C22—C23—C24—C19	0.8 (4)
C1—C6—C8—C9	0.1 (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—C23	179.4 (2)
Fe1—N1—C10—C9	−176.04 (19)	C20—C19—C24—C23	−0.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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.

Experimental details

Crystal data
Chemical formula	[FeCl₂(C₂₅H₁₉N₃)]
M_r	488.18
Crystal system, space group	Triclinic, 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)
V (Å³)	1044.35 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.00
Crystal size (mm)	0.30 × 0.10 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.754, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	9910, 4757, 3954
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.108, 1.05
No. of reflections	4757
No. of parameters	292
No. of restraints	7
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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—N1	2.2386 (19)	Fe1—Cl1	2.3636 (8)
Fe1—N2	2.103 (2)	Fe1—Cl2	2.2748 (7)
Fe1—N3	2.2523 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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.

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

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