(2-Chloro­pyrimidin-4-yl)ferrocene

Shi, G.-Q.; Li, Y.; Gao, X.; Hao, L.-F.; Zhao, W.

doi:10.1107/S1600536814004917

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 4| April 2014| Page m130

doi:10.1107/S1600536814004917

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(2-Chloropyrimidin-4-yl)ferrocene

Guo-Qing Shi,^a,^b Yang Li,^c Xiang Gao,^c Long-Fei Hao ^c and Wen-en Zhao ^a ^*

^aSchool of Chemical Engineering and Energy, Zhengzhou University, Henan, Zhengzhou 450001, People's Republic of China, ^bSchool of Food and Bioengineering, Zhengzhou University of Light Industry, Henan, Zhengzhou 450001, People's Republic of China, and ^cCollege of Chemistry and Molecular Engineering, Zhengzhou University, Henan, Zhengzhou 450001, People's Republic of China
^*Correspondence e-mail: zhaowenen@zzu.edu.cn

(Received 23 February 2014; accepted 3 March 2014; online 12 March 2014)

In the title compound, [Fe(C₅H₅)(C₉H₆ClN₂)], the two cyclopentadienyl rings are almost parallel, subtending a dihedral angle of 3.01 (5)°. The dihedral angle between the substituted cyclopentadienyl ring and the pyrimidinyl ring is 12.02 (1)°. The conformation of the two cyclopentadienyl rings in the ferrocenyl moiety is eclipsed.

CCDC reference: 989734

Related literature

For pyrimidinyl derivatives, see: Chinchilla et al. (2004 ); Walker et al. (2009 ). For ferrocenyl pyrimidines, see: Xu et al. (2009 , 2010 ). For the synthesis of the title compound, see: Xu et al. (2014 ).

Experimental

Crystal data

[Fe(C₅H₅)(C₉H₆ClN₂)]
M_r = 298.55
Monoclinic, P 2₁ /c
a = 10.5064 (18) Å
b = 10.2684 (17) Å
c = 11.843 (2) Å
β = 108.580 (2)°
V = 1211.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.45 mm⁻¹
T = 296 K
0.43 × 0.15 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.575, T_max = 0.846
8932 measured reflections
2251 independent reflections
1777 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.111
S = 0.73
2251 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); 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: SHELXL97.

Supporting information

CCDC reference: 989734

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814004917/fj2665sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814004917/fj2665Isup2.hkl

checkCIF report

Comment top

Pyrimidines are widespread heterocyclic motifs found in many natural products and pharmaceuticals (Chinchilla et al., 2004; Walker et al., 2009). In addition, ferrocenyl pyrimidines as ligands are used in organometallic catalysis (Xu et al., 2009,2010). Here we report the crystal structure of the title compound, obtained from the via the coupling reaction of chloromercuriferrocene and 4,6-dichloropyrimidine.

A view on the molecular structure of the title compound is given in the figure 1. The two cyclopentadienyl rings are almost parallel with dihedral angles of 3.01 (5)°. The dihedral angle between the substituted cyclopentadienyl and pyrimidinyl ring is 12.02 (1)°. The nitrogen and chlorine atoms of pyrimidinyl ring do not participate in hydrogen bond.

Related literature top

For pyrimidinyl derivatives, see: Chinchilla et al. (2004); Walker et al. (2009). For ferrocenyl pyrimidines, see: Xu et al. (2009, 2010). For the synthesis of the title compound, see: Xu et al. (2014).

Experimental top

The title compound was prepared as described in literature (Xu et al. 2014) and recrystallized from dichloromethane/petroleum ether solution at room temperature to give the desired crystals suitable for single-crystal X-ray diffraction.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with displacement ellipsoids at the 30% probability level.

(2-Chloropyrimidin-4-yl)ferrocene top

Crystal data top

[Fe(C₅H₅)(C₉H₆ClN₂)]	F(000) = 608
M_r = 298.55	D_x = 1.637 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2413 reflections
a = 10.5064 (18) Å	θ = 2.7–24.7°
b = 10.2684 (17) Å	µ = 1.45 mm⁻¹
c = 11.843 (2) Å	T = 296 K
β = 108.580 (2)°	Block, red
V = 1211.1 (4) Å³	0.43 × 0.15 × 0.12 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2251 independent reflections
Radiation source: fine-focus sealed tube	1777 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
phi and ω scans	θ_max = 25.5°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
T_min = 0.575, T_max = 0.846	k = −12→12
8932 measured reflections	l = −14→14

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 0.73	w = 1/[σ²(F_o²) + (0.1P)² + 1.P] where P = (F_o² + 2F_c²)/3
2251 reflections	(Δ/σ)_max = 0.001
163 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₉H₆ClN₂)]	V = 1211.1 (4) Å³
M_r = 298.55	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.5064 (18) Å	µ = 1.45 mm⁻¹
b = 10.2684 (17) Å	T = 296 K
c = 11.843 (2) Å	0.43 × 0.15 × 0.12 mm
β = 108.580 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2251 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1777 reflections with I > 2σ(I)
T_min = 0.575, T_max = 0.846	R_int = 0.034
8932 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 0.73	Δρ_max = 0.28 e Å⁻³
2251 reflections	Δρ_min = −0.23 e Å⁻³
163 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
Fe1	0.83734 (4)	0.37324 (4)	0.13102 (3)	0.03675 (17)
Cl1	0.30992 (10)	0.08466 (10)	0.06208 (8)	0.0682 (3)
N1	0.4864 (2)	0.2434 (2)	0.0285 (2)	0.0417 (6)
N2	0.3649 (3)	0.1085 (3)	−0.1350 (2)	0.0508 (7)
C1	0.6492 (3)	0.4015 (3)	0.0148 (3)	0.0385 (6)
C2	0.6641 (3)	0.4632 (3)	0.1266 (3)	0.0437 (7)
H2	0.6107	0.4447	0.1791	0.052*
C3	0.7683 (3)	0.5561 (3)	0.1477 (3)	0.0493 (8)
H3	0.8004	0.6120	0.2182	0.059*
C4	0.8204 (3)	0.5527 (3)	0.0520 (3)	0.0489 (8)
H4	0.8948	0.6057	0.0444	0.059*
C5	0.7475 (3)	0.4585 (3)	−0.0309 (3)	0.0419 (7)
H5	0.7626	0.4353	−0.1059	0.050*
C6	0.8598 (4)	0.1813 (3)	0.1773 (4)	0.0639 (10)
H6	0.7911	0.1132	0.1529	0.077*
C7	0.9520 (5)	0.2188 (5)	0.1171 (4)	0.0812 (14)
H7	0.9582	0.1812	0.0430	0.097*
C8	1.0339 (4)	0.3189 (5)	0.1849 (4)	0.0733 (12)
H8	1.1066	0.3637	0.1654	0.088*
C9	0.9945 (4)	0.3419 (4)	0.2828 (3)	0.0655 (11)
H9	1.0339	0.4064	0.3451	0.079*
C10	0.8885 (4)	0.2581 (4)	0.2782 (3)	0.0583 (9)
H10	0.8409	0.2548	0.3372	0.070*
C11	0.5533 (3)	0.2986 (3)	−0.0397 (2)	0.0389 (6)
C12	0.5267 (3)	0.2604 (3)	−0.1578 (3)	0.0457 (7)
H12	0.5714	0.2980	−0.2059	0.055*
C13	0.4320 (3)	0.1651 (3)	−0.2007 (3)	0.0511 (8)
H13	0.4136	0.1385	−0.2793	0.061*
C14	0.3983 (3)	0.1538 (3)	−0.0259 (3)	0.0464 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0331 (3)	0.0351 (3)	0.0377 (3)	−0.00076 (15)	0.00512 (18)	0.00464 (15)
Cl1	0.0639 (6)	0.0770 (6)	0.0607 (6)	−0.0252 (5)	0.0156 (4)	0.0025 (5)
N1	0.0371 (12)	0.0417 (13)	0.0414 (13)	0.0004 (10)	0.0053 (10)	−0.0030 (10)
N2	0.0431 (15)	0.0503 (15)	0.0523 (16)	−0.0046 (11)	0.0059 (13)	−0.0119 (12)
C1	0.0355 (15)	0.0343 (13)	0.0390 (15)	0.0042 (11)	0.0024 (12)	0.0005 (11)
C2	0.0378 (15)	0.0423 (16)	0.0481 (16)	0.0026 (13)	0.0095 (13)	−0.0074 (13)
C3	0.0484 (18)	0.0362 (15)	0.0559 (18)	−0.0029 (13)	0.0063 (15)	−0.0104 (13)
C4	0.0500 (18)	0.0353 (15)	0.0556 (19)	−0.0059 (13)	0.0088 (15)	0.0069 (13)
C5	0.0450 (16)	0.0376 (15)	0.0387 (14)	0.0016 (13)	0.0074 (12)	0.0071 (12)
C6	0.062 (2)	0.0346 (17)	0.075 (2)	0.0047 (15)	−0.0064 (19)	0.0087 (16)
C7	0.099 (3)	0.087 (3)	0.055 (2)	0.062 (3)	0.021 (2)	0.015 (2)
C8	0.0395 (19)	0.086 (3)	0.090 (3)	0.0114 (19)	0.0146 (19)	0.040 (3)
C9	0.057 (2)	0.057 (2)	0.060 (2)	−0.0097 (17)	−0.0145 (18)	0.0175 (17)
C10	0.062 (2)	0.059 (2)	0.0475 (18)	−0.0065 (16)	0.0076 (16)	0.0178 (16)
C11	0.0343 (14)	0.0360 (14)	0.0399 (15)	0.0084 (11)	0.0027 (12)	0.0004 (11)
C12	0.0400 (16)	0.0533 (18)	0.0403 (16)	−0.0010 (13)	0.0081 (13)	−0.0074 (13)
C13	0.0447 (18)	0.0585 (19)	0.0440 (17)	0.0015 (15)	0.0056 (14)	−0.0140 (15)
C14	0.0396 (16)	0.0430 (16)	0.0508 (18)	−0.0013 (13)	0.0064 (14)	0.0020 (13)

Geometric parameters (Å, º) top

Fe1—C2	2.027 (3)	C3—C4	1.408 (5)
Fe1—C7	2.029 (4)	C3—H3	0.9800
Fe1—C10	2.032 (3)	C4—C5	1.416 (4)
Fe1—C8	2.036 (4)	C4—H4	0.9800
Fe1—C1	2.038 (3)	C5—H5	0.9800
Fe1—C6	2.040 (3)	C6—C10	1.383 (5)
Fe1—C9	2.042 (3)	C6—C7	1.426 (6)
Fe1—C3	2.045 (3)	C6—H6	0.9800
Fe1—C5	2.045 (3)	C7—C8	1.415 (6)
Fe1—C4	2.049 (3)	C7—H7	0.9800
Cl1—C14	1.751 (3)	C8—C9	1.370 (6)
N1—C14	1.319 (4)	C8—H8	0.9800
N1—C11	1.352 (4)	C9—C10	1.395 (5)
N2—C14	1.313 (4)	C9—H9	0.9800
N2—C13	1.337 (4)	C10—H10	0.9800
C1—C2	1.430 (4)	C11—C12	1.394 (4)
C1—C5	1.436 (4)	C12—C13	1.372 (4)
C1—C11	1.461 (4)	C12—H12	0.9300
C2—C3	1.413 (4)	C13—H13	0.9300
C2—H2	0.9800

C2—Fe1—C7	154.86 (19)	C4—C3—Fe1	70.02 (17)
C2—Fe1—C10	106.10 (15)	C2—C3—Fe1	69.01 (16)
C7—Fe1—C10	67.27 (16)	C4—C3—H3	125.7
C2—Fe1—C8	161.11 (18)	C2—C3—H3	125.7
C7—Fe1—C8	40.73 (19)	Fe1—C3—H3	125.7
C10—Fe1—C8	66.88 (16)	C3—C4—C5	108.2 (3)
C2—Fe1—C1	41.18 (12)	C3—C4—Fe1	69.75 (17)
C7—Fe1—C1	121.99 (16)	C5—C4—Fe1	69.62 (16)
C10—Fe1—C1	126.63 (14)	C3—C4—H4	125.9
C8—Fe1—C1	156.89 (17)	C5—C4—H4	125.9
C2—Fe1—C6	118.27 (15)	Fe1—C4—H4	125.9
C7—Fe1—C6	41.04 (17)	C4—C5—C1	108.2 (3)
C10—Fe1—C6	39.72 (15)	C4—C5—Fe1	69.89 (17)
C8—Fe1—C6	68.40 (16)	C1—C5—Fe1	69.14 (15)
C1—Fe1—C6	108.89 (13)	C4—C5—H5	125.9
C2—Fe1—C9	124.24 (16)	C1—C5—H5	125.9
C7—Fe1—C9	67.28 (18)	Fe1—C5—H5	125.9
C10—Fe1—C9	40.06 (15)	C10—C6—C7	106.4 (3)
C8—Fe1—C9	39.26 (17)	C10—C6—Fe1	69.84 (19)
C1—Fe1—C9	162.82 (16)	C7—C6—Fe1	69.1 (2)
C6—Fe1—C9	67.62 (15)	C10—C6—H6	126.8
C2—Fe1—C3	40.60 (12)	C7—C6—H6	126.8
C7—Fe1—C3	164.41 (19)	Fe1—C6—H6	126.8
C10—Fe1—C3	117.13 (15)	C8—C7—C6	107.5 (4)
C8—Fe1—C3	125.25 (17)	C8—C7—Fe1	69.9 (2)
C1—Fe1—C3	68.70 (12)	C6—C7—Fe1	69.9 (2)
C6—Fe1—C3	151.12 (16)	C8—C7—H7	126.3
C9—Fe1—C3	105.78 (15)	C6—C7—H7	126.3
C2—Fe1—C5	68.79 (13)	Fe1—C7—H7	126.3
C7—Fe1—C5	111.52 (14)	C9—C8—C7	108.2 (4)
C10—Fe1—C5	166.08 (13)	C9—C8—Fe1	70.6 (2)
C8—Fe1—C5	122.01 (15)	C7—C8—Fe1	69.4 (2)
C1—Fe1—C5	41.17 (12)	C9—C8—H8	125.9
C6—Fe1—C5	130.18 (14)	C7—C8—H8	125.9
C9—Fe1—C5	153.51 (14)	Fe1—C8—H8	125.9
C3—Fe1—C5	68.03 (12)	C8—C9—C10	108.3 (4)
C2—Fe1—C4	68.38 (13)	C8—C9—Fe1	70.1 (2)
C7—Fe1—C4	129.28 (17)	C10—C9—Fe1	69.58 (19)
C10—Fe1—C4	151.17 (14)	C8—C9—H9	125.9
C8—Fe1—C4	108.75 (15)	C10—C9—H9	125.9
C1—Fe1—C4	68.83 (12)	Fe1—C9—H9	125.9
C6—Fe1—C4	167.93 (16)	C6—C10—C9	109.7 (3)
C9—Fe1—C4	118.17 (14)	C6—C10—Fe1	70.44 (19)
C3—Fe1—C4	40.24 (13)	C9—C10—Fe1	70.36 (19)
C5—Fe1—C4	40.49 (12)	C6—C10—H10	125.2
C14—N1—C11	114.7 (3)	C9—C10—H10	125.2
C14—N2—C13	113.2 (3)	Fe1—C10—H10	125.2
C2—C1—C5	106.8 (3)	N1—C11—C12	120.4 (3)
C2—C1—C11	125.9 (3)	N1—C11—C1	117.1 (2)
C5—C1—C11	127.3 (3)	C12—C11—C1	122.5 (3)
C2—C1—Fe1	69.01 (16)	C13—C12—C11	117.5 (3)
C5—C1—Fe1	69.69 (16)	C13—C12—H12	121.2
C11—C1—Fe1	125.37 (19)	C11—C12—H12	121.2
C3—C2—C1	108.3 (3)	N2—C13—C12	123.3 (3)
C3—C2—Fe1	70.38 (17)	N2—C13—H13	118.3
C1—C2—Fe1	69.81 (16)	C12—C13—H13	118.3
C3—C2—H2	125.9	N2—C14—N1	130.9 (3)
C1—C2—H2	125.9	N2—C14—Cl1	114.6 (2)
Fe1—C2—H2	125.9	N1—C14—Cl1	114.5 (2)
C4—C3—C2	108.6 (3)

C7—Fe1—C1—C2	155.1 (2)	C8—Fe1—C6—C10	79.4 (3)
C10—Fe1—C1—C2	71.0 (2)	C1—Fe1—C6—C10	−125.1 (2)
C8—Fe1—C1—C2	−169.3 (4)	C9—Fe1—C6—C10	36.9 (2)
C6—Fe1—C1—C2	111.7 (2)	C3—Fe1—C6—C10	−45.2 (4)
C9—Fe1—C1—C2	36.5 (5)	C5—Fe1—C6—C10	−166.3 (2)
C3—Fe1—C1—C2	−37.63 (18)	C4—Fe1—C6—C10	157.9 (6)
C5—Fe1—C1—C2	−118.2 (2)	C2—Fe1—C6—C7	161.4 (2)
C4—Fe1—C1—C2	−80.94 (19)	C10—Fe1—C6—C7	−117.5 (3)
C2—Fe1—C1—C5	118.2 (2)	C8—Fe1—C6—C7	−38.1 (3)
C7—Fe1—C1—C5	−86.7 (2)	C1—Fe1—C6—C7	117.4 (2)
C10—Fe1—C1—C5	−170.79 (19)	C9—Fe1—C6—C7	−80.6 (3)
C8—Fe1—C1—C5	−51.1 (4)	C3—Fe1—C6—C7	−162.7 (3)
C6—Fe1—C1—C5	−130.1 (2)	C5—Fe1—C6—C7	76.2 (3)
C9—Fe1—C1—C5	154.7 (4)	C4—Fe1—C6—C7	40.4 (7)
C3—Fe1—C1—C5	80.55 (18)	C10—C6—C7—C8	−0.2 (4)
C4—Fe1—C1—C5	37.24 (17)	Fe1—C6—C7—C8	60.0 (2)
C2—Fe1—C1—C11	−119.8 (3)	C10—C6—C7—Fe1	−60.2 (2)
C7—Fe1—C1—C11	35.2 (3)	C2—Fe1—C7—C8	−159.8 (3)
C10—Fe1—C1—C11	−48.8 (3)	C10—Fe1—C7—C8	−80.4 (3)
C8—Fe1—C1—C11	70.9 (5)	C1—Fe1—C7—C8	159.5 (2)
C6—Fe1—C1—C11	−8.2 (3)	C6—Fe1—C7—C8	−118.4 (3)
C9—Fe1—C1—C11	−83.3 (5)	C9—Fe1—C7—C8	−36.9 (2)
C3—Fe1—C1—C11	−157.5 (3)	C3—Fe1—C7—C8	29.3 (7)
C5—Fe1—C1—C11	122.0 (3)	C5—Fe1—C7—C8	114.5 (2)
C4—Fe1—C1—C11	159.2 (3)	C4—Fe1—C7—C8	71.7 (3)
C5—C1—C2—C3	0.4 (3)	C2—Fe1—C7—C6	−41.4 (4)
C11—C1—C2—C3	179.3 (3)	C10—Fe1—C7—C6	37.9 (2)
Fe1—C1—C2—C3	60.1 (2)	C8—Fe1—C7—C6	118.4 (3)
C5—C1—C2—Fe1	−59.72 (19)	C1—Fe1—C7—C6	−82.2 (2)
C11—C1—C2—Fe1	119.2 (3)	C9—Fe1—C7—C6	81.5 (2)
C7—Fe1—C2—C3	−176.3 (3)	C3—Fe1—C7—C6	147.7 (5)
C10—Fe1—C2—C3	113.1 (2)	C5—Fe1—C7—C6	−127.1 (2)
C8—Fe1—C2—C3	47.9 (5)	C4—Fe1—C7—C6	−169.9 (2)
C1—Fe1—C2—C3	−119.1 (3)	C6—C7—C8—C9	0.2 (4)
C6—Fe1—C2—C3	154.2 (2)	Fe1—C7—C8—C9	60.2 (3)
C9—Fe1—C2—C3	73.2 (2)	C6—C7—C8—Fe1	−60.0 (2)
C5—Fe1—C2—C3	−80.56 (19)	C2—Fe1—C8—C9	34.0 (6)
C4—Fe1—C2—C3	−36.93 (18)	C7—Fe1—C8—C9	−119.1 (3)
C7—Fe1—C2—C1	−57.2 (4)	C10—Fe1—C8—C9	−37.6 (2)
C10—Fe1—C2—C1	−127.83 (19)	C1—Fe1—C8—C9	−168.3 (3)
C8—Fe1—C2—C1	167.0 (4)	C6—Fe1—C8—C9	−80.6 (3)
C6—Fe1—C2—C1	−86.8 (2)	C3—Fe1—C8—C9	70.2 (3)
C9—Fe1—C2—C1	−167.72 (18)	C5—Fe1—C8—C9	154.6 (2)
C3—Fe1—C2—C1	119.1 (3)	C4—Fe1—C8—C9	111.9 (2)
C5—Fe1—C2—C1	38.49 (17)	C2—Fe1—C8—C7	153.0 (4)
C4—Fe1—C2—C1	82.13 (18)	C10—Fe1—C8—C7	81.5 (3)
C1—C2—C3—C4	−0.8 (3)	C1—Fe1—C8—C7	−49.2 (5)
Fe1—C2—C3—C4	59.0 (2)	C6—Fe1—C8—C7	38.4 (2)
C1—C2—C3—Fe1	−59.8 (2)	C9—Fe1—C8—C7	119.1 (4)
C2—Fe1—C3—C4	−120.2 (3)	C3—Fe1—C8—C7	−170.7 (2)
C7—Fe1—C3—C4	53.9 (6)	C5—Fe1—C8—C7	−86.4 (3)
C10—Fe1—C3—C4	156.68 (19)	C4—Fe1—C8—C7	−129.1 (2)
C8—Fe1—C3—C4	76.9 (2)	C7—C8—C9—C10	−0.1 (4)
C1—Fe1—C3—C4	−81.99 (19)	Fe1—C8—C9—C10	59.3 (3)
C6—Fe1—C3—C4	−172.7 (3)	C7—C8—C9—Fe1	−59.5 (2)
C9—Fe1—C3—C4	115.2 (2)	C2—Fe1—C9—C8	−167.4 (2)
C5—Fe1—C3—C4	−37.55 (17)	C7—Fe1—C9—C8	38.2 (3)
C7—Fe1—C3—C2	174.1 (5)	C10—Fe1—C9—C8	119.4 (4)
C10—Fe1—C3—C2	−83.2 (2)	C1—Fe1—C9—C8	164.3 (4)
C8—Fe1—C3—C2	−162.9 (2)	C6—Fe1—C9—C8	82.8 (3)
C1—Fe1—C3—C2	38.16 (18)	C3—Fe1—C9—C8	−127.0 (3)
C6—Fe1—C3—C2	−52.6 (3)	C5—Fe1—C9—C8	−54.8 (4)
C9—Fe1—C3—C2	−124.7 (2)	C4—Fe1—C9—C8	−85.5 (3)
C5—Fe1—C3—C2	82.60 (19)	C2—Fe1—C9—C10	73.2 (3)
C4—Fe1—C3—C2	120.2 (3)	C7—Fe1—C9—C10	−81.2 (3)
C2—C3—C4—C5	0.8 (3)	C8—Fe1—C9—C10	−119.4 (4)
Fe1—C3—C4—C5	59.2 (2)	C1—Fe1—C9—C10	44.9 (6)
C2—C3—C4—Fe1	−58.4 (2)	C6—Fe1—C9—C10	−36.6 (2)
C2—Fe1—C4—C3	37.25 (17)	C3—Fe1—C9—C10	113.6 (2)
C7—Fe1—C4—C3	−163.7 (2)	C5—Fe1—C9—C10	−174.2 (3)
C10—Fe1—C4—C3	−46.9 (4)	C4—Fe1—C9—C10	155.1 (2)
C8—Fe1—C4—C3	−122.8 (2)	C7—C6—C10—C9	0.1 (4)
C1—Fe1—C4—C3	81.64 (19)	Fe1—C6—C10—C9	−59.6 (3)
C6—Fe1—C4—C3	162.9 (6)	C7—C6—C10—Fe1	59.7 (2)
C9—Fe1—C4—C3	−81.1 (2)	C8—C9—C10—C6	0.0 (4)
C5—Fe1—C4—C3	119.5 (3)	Fe1—C9—C10—C6	59.7 (2)
C2—Fe1—C4—C5	−82.23 (19)	C8—C9—C10—Fe1	−59.6 (3)
C7—Fe1—C4—C5	76.8 (3)	C2—Fe1—C10—C6	115.1 (2)
C10—Fe1—C4—C5	−166.4 (3)	C7—Fe1—C10—C6	−39.1 (3)
C8—Fe1—C4—C5	117.7 (2)	C8—Fe1—C10—C6	−83.5 (3)
C1—Fe1—C4—C5	−37.85 (18)	C1—Fe1—C10—C6	74.7 (3)
C6—Fe1—C4—C5	43.5 (7)	C9—Fe1—C10—C6	−120.4 (3)
C9—Fe1—C4—C5	159.5 (2)	C3—Fe1—C10—C6	157.4 (2)
C3—Fe1—C4—C5	−119.5 (3)	C5—Fe1—C10—C6	48.7 (7)
C3—C4—C5—C1	−0.6 (3)	C4—Fe1—C10—C6	−170.6 (3)
Fe1—C4—C5—C1	58.73 (19)	C2—Fe1—C10—C9	−124.5 (3)
C3—C4—C5—Fe1	−59.3 (2)	C7—Fe1—C10—C9	81.2 (3)
C2—C1—C5—C4	0.1 (3)	C8—Fe1—C10—C9	36.8 (3)
C11—C1—C5—C4	−178.8 (3)	C1—Fe1—C10—C9	−164.9 (2)
Fe1—C1—C5—C4	−59.2 (2)	C6—Fe1—C10—C9	120.4 (3)
C2—C1—C5—Fe1	59.28 (19)	C3—Fe1—C10—C9	−82.3 (3)
C11—C1—C5—Fe1	−119.6 (3)	C5—Fe1—C10—C9	169.1 (5)
C2—Fe1—C5—C4	81.1 (2)	C4—Fe1—C10—C9	−50.2 (4)
C7—Fe1—C5—C4	−125.9 (2)	C14—N1—C11—C12	0.3 (4)
C10—Fe1—C5—C4	151.9 (6)	C14—N1—C11—C1	178.1 (3)
C8—Fe1—C5—C4	−81.5 (3)	C2—C1—C11—N1	−10.2 (4)
C1—Fe1—C5—C4	119.6 (3)	C5—C1—C11—N1	168.4 (3)
C6—Fe1—C5—C4	−169.2 (2)	Fe1—C1—C11—N1	78.1 (3)
C9—Fe1—C5—C4	−43.9 (4)	C2—C1—C11—C12	167.5 (3)
C3—Fe1—C5—C4	37.33 (18)	C5—C1—C11—C12	−13.8 (4)
C2—Fe1—C5—C1	−38.51 (17)	Fe1—C1—C11—C12	−104.2 (3)
C7—Fe1—C5—C1	114.5 (2)	N1—C11—C12—C13	−0.6 (4)
C10—Fe1—C5—C1	32.2 (6)	C1—C11—C12—C13	−178.2 (3)
C8—Fe1—C5—C1	158.9 (2)	C14—N2—C13—C12	0.4 (5)
C6—Fe1—C5—C1	71.2 (2)	C11—C12—C13—N2	0.2 (5)
C9—Fe1—C5—C1	−163.6 (3)	C13—N2—C14—N1	−0.8 (5)
C3—Fe1—C5—C1	−82.32 (18)	C13—N2—C14—Cl1	178.7 (2)
C4—Fe1—C5—C1	−119.6 (3)	C11—N1—C14—N2	0.4 (5)
C2—Fe1—C6—C10	−81.1 (2)	C11—N1—C14—Cl1	−179.0 (2)
C7—Fe1—C6—C10	117.5 (3)

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₉H₆ClN₂)]
M_r	298.55
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.5064 (18), 10.2684 (17), 11.843 (2)
β (°)	108.580 (2)
V (Å³)	1211.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.45
Crystal size (mm)	0.43 × 0.15 × 0.12

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.575, 0.846
No. of measured, independent and observed [I > 2σ(I)] reflections	8932, 2251, 1777
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.111, 0.73
No. of reflections	2251
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.23

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was sponsored by the National Natural Science Foundation of China (No. 21102135).

References

Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chinchilla, R., Najera, C. & Yus, M. (2004). Chem. Rev. 104, 2667–2722. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Walker, S. R., Carter, E. J., Huff, B. C. & Morris, J. C. (2009). Chem. Rev. 109, 3080–3098. Web of Science CrossRef PubMed CAS Google Scholar
Xu, C., Li, H. M., Wang, Z. Q., Lou, X. H. & Fu, W. J. (2014). Monatsh. Chem. 145 doi:10.1007/s00706-013-1142-0. Google Scholar
Xu, C., Wang, Z. Q., Fu, W. J., Lou, X. H., Li, Y. F., Cen, F. F., Ma, H. J. & Ji, B. M. (2009). Organometallics, 28, 1909–1916. Web of Science CSD CrossRef CAS Google Scholar
Xu, C., Zhang, Y. P., Wang, Z. Q., Fu, W. J., Hao, X. Q., Xu, Y. & Ji, B. M. (2010). Chem. Commun. 46, 6852–6854. Web of Science CSD CrossRef CAS Google Scholar