Quinolinium tetra­chloro­ferrate(III)

In the title compound, (C₉H₈N)[FeCl₄], the tetra­chloro­ferrate(III) anion lies on a mirror plane, whereas the quinolinium cation has inversion symmetry as the result of orientational disorder. In the crystal structure, C—H...Cl inter­actions between the ions form zigzag ribbons along the b axis. These ribbons are linked via Fe—Cl...π inter­actions, forming a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in main residue
• R factor = 0.040
• wR factor = 0.101
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Fe1
PLAT301_ALERT_3_C Main Residue  Disorder .........................       9.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C3     -   C4     ...       1.37 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C3     -   C3_b   ...       1.39 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1     ..  CL2     ..       2.87 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: KM-4 Software (Oxford Diffraction, 1989); cell refinement: KM-4 Software; data reduction: KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Quinolinium tetrachloroferrate(III)

Crystal data

(C9H8N)[FeCl4]	F(000) = 652
Mr = 327.81	Dx = 1.708 Mg m^−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 50 reflections
a = 9.211 (2) Å	θ = 2.5–25.0°
b = 14.162 (3) Å	µ = 1.99 mm^−1
c = 9.772 (2) Å	T = 295 K
V = 1274.7 (5) Å^3	Prism, yellow–orange
Z = 4	0.5 × 0.3 × 0.2 mm

Data collection

Kuma KM-4 diffractometer	640 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.076
Graphite monochromator	θmax = 25.0°, θmin = 2.5°
θ/2θ scans	h = −10→2
Absorption correction: ψ scan (North et al., 1968)	k = 0→16
Tmin = 0.499, Tmax = 0.672	l = 0→11
1489 measured reflections	3 standard reflections every 200 reflections
1174 independent reflections	intensity decay: 2.5%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.101	w = 1/[σ^2(Fo^2) + (0.0506P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
1174 reflections	Δρmax = 0.35 e Å^−3
74 parameters	Δρmin = −0.36 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0095 (15)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Fe1	0.23365 (9)	0.7500	0.02672 (8)	0.0446 (3)
Cl1	0.09997 (13)	0.62250 (9)	0.01752 (13)	0.0687 (4)
Cl2	0.38686 (17)	0.7500	−0.14284 (18)	0.0641 (5)
Cl3	0.3527 (2)	0.7500	0.22088 (16)	0.0719 (5)
C1	0.6812 (6)	0.5750 (4)	−0.1542 (7)	0.0822 (16)
H1	0.7394	0.5955	−0.2261	0.099*
C2	0.5741 (6)	0.5123 (3)	−0.1743 (5)	0.0771 (14)	0.50
H2A	0.5575	0.4888	−0.2617	0.092*	0.50
N2	0.5741 (6)	0.5123 (3)	−0.1743 (5)	0.0771 (14)	0.50
H2B	0.5588	0.4905	−0.2551	0.092*	0.50
C3	0.4862 (4)	0.4818 (3)	−0.0649 (4)	0.0460 (11)
C4	0.3771 (5)	0.4169 (3)	−0.0832 (5)	0.0591 (11)
H4	0.3601	0.3916	−0.1696	0.071*
C5	0.2958 (6)	0.3900 (4)	0.0219 (7)	0.0779 (16)
H5	0.2215	0.3467	0.0074	0.094*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0500 (6)	0.0403 (5)	0.0437 (5)	0.000	−0.0006 (4)	0.000
Cl1	0.0756 (8)	0.0602 (7)	0.0703 (8)	−0.0222 (6)	0.0062 (6)	−0.0042 (6)
Cl2	0.0564 (10)	0.0691 (10)	0.0667 (10)	0.000	0.0121 (8)	0.000
Cl3	0.0887 (13)	0.0710 (11)	0.0560 (11)	0.000	−0.0222 (9)	0.000
C1	0.071 (4)	0.064 (3)	0.111 (5)	0.011 (3)	0.027 (3)	0.031 (4)
C2	0.099 (4)	0.075 (3)	0.057 (3)	0.026 (3)	0.005 (3)	0.003 (3)
N2	0.099 (4)	0.075 (3)	0.057 (3)	0.026 (3)	0.005 (3)	0.003 (3)
C3	0.058 (3)	0.039 (2)	0.041 (2)	0.010 (2)	−0.005 (2)	0.0025 (17)
C4	0.065 (3)	0.047 (3)	0.065 (3)	0.004 (2)	−0.010 (3)	−0.003 (2)
C5	0.060 (3)	0.051 (3)	0.122 (5)	0.004 (3)	−0.018 (3)	−0.007 (3)

Geometric parameters (Å, º)

Fe1—Cl2	2.1765 (19)	N2—C3	1.409 (7)
Fe1—Cl1	2.1873 (12)	N2—H2B	0.8600
Fe1—Cl1^i	2.1873 (12)	C3—C4	1.373 (6)
Fe1—Cl3	2.1915 (17)	C3—C3^ii	1.393 (8)
C1—N2	1.341 (7)	C4—C5	1.326 (7)
C1—C5^ii	1.401 (8)	C4—H4	0.9300
C1—H1	0.9300	C5—C1^ii	1.401 (8)
C2—C3	1.409 (7)	C5—H5	0.9299
C2—H2A	0.9300
Cl2—Fe1—Cl1	109.49 (5)	C4—C3—N2	121.8 (4)
Cl2—Fe1—Cl1^i	109.49 (5)	C3^ii—C3—N2	118.1 (5)
Cl1—Fe1—Cl1^i	111.27 (8)	C5^ii—C1—H1	120.0
Cl2—Fe1—Cl3	109.55 (8)	C4—C3—C3^ii	120.0 (5)
Cl1—Fe1—Cl3	108.50 (5)	C5—C4—C3	120.3 (5)
Cl1^i—Fe1—Cl3	108.50 (5)	C5—C4—H4	119.8
N2—C1—C5^ii	118.7 (5)	C3—C4—H4	119.9
N2—C1—H1	121.3	C4—C5—C1^ii	121.8 (5)
C1—N2—C3	121.0 (5)	C4—C5—H5	119.1
C1—N2—H2B	119.5	C1^ii—C5—H5	119.1
C3—N2—H2B	119.5
C5^ii—C1—N2—C3	−0.3 (7)	C3^ii—C3—C4—C5	1.3 (7)
C1—N2—C3—C4	−179.2 (4)	N2—C3—C4—C5	−179.6 (5)
C1—N2—C3—C3^ii	−0.1 (7)	C3—C4—C5—C1^ii	−0.9 (7)

Symmetry codes: (i) x, −y+3/2, z; (ii) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl2^iii	0.93	2.87	3.697 (6)	148

Symmetry code: (iii) x+1/2, −y+3/2, −z−1/2.