Benzyl-triethyl-ammonium tetra-chlorido-ferrate(III).

In the title mol-ecular salt, (C(13)H(22)N)[FeCl(4)], three of the chloride ions of the tetra-hedral Fe(III)-containing anion are disordered over two orientations in a 0.656 (11):0.344 (11) ratio. In the crystal, there are no identifiable directional inter-actions between cations and anions except for Coulombic forces.

Related literature

For background to mol­ecular–ionic ferroelectrics, see: Zhang et al. (2010 ▶).

Experimental

Crystal data

(C13H22N)[FeCl4]

M = 389.97

Orthorhombic,

a = 15.514 (3) Å

b = 15.021 (3) Å

c = 16.155 (3) Å

V = 3764.7 (13) Å3

Z = 8

Mo Kα radiation

μ = 1.36 mm−1

T = 293 K

0.26 × 0.24 × 0.20 mm

Data collection

Rigaku Mercury2 CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.655, T max = 0.734

32945 measured reflections

3691 independent reflections

2364 reflections with I > 2σ(I)

R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.170

S = 1.04

3691 reflections

204 parameters

156 restraints

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812023008/hb6797sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023008/hb6797Isup2.hkl

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

(C13H22N)[FeCl4]	F(000) = 1608
Mr = 389.97	Dx = 1.376 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	θ = 3.0–26°
a = 15.514 (3) Å	µ = 1.36 mm−1
b = 15.021 (3) Å	T = 293 K
c = 16.155 (3) Å	Block, orange
V = 3764.7 (13) Å3	0.26 × 0.24 × 0.20 mm
Z = 8

Rigaku Mercury2 CCD diffractometer	3691 independent reflections
Radiation source: fine-focus sealed tube	2364 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.082
Detector resolution: 13.6612 pixels mm-1	θmax = 26.0°, θmin = 3.0°
CCD_Profile_fitting scans	h = −19→19
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −18→18
Tmin = 0.655, Tmax = 0.734	l = −19→19
32945 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.068	H-atom parameters constrained
wR(F2) = 0.170	w = 1/[σ2(Fo2) + (0.0625P)2 + 5.6146P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.009
3691 reflections	Δρmax = 0.73 e Å−3
204 parameters	Δρmin = −0.38 e Å−3
156 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0092 (7)

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.7598 (3)	0.8752 (4)	0.3510 (3)	0.0664 (14)
H1A	0.8189	0.8604	0.3369	0.080*
H1B	0.7231	0.8513	0.3078	0.080*
C2	0.7509 (4)	0.9749 (4)	0.3512 (4)	0.0816 (17)
H2A	0.6920	0.9906	0.3619	0.122*
H2B	0.7679	0.9980	0.2982	0.122*
H2C	0.7871	0.9996	0.3935	0.122*
C3	0.6454 (3)	0.8524 (3)	0.4582 (3)	0.0585 (13)
H3A	0.6316	0.8189	0.5078	0.070*
H3B	0.6437	0.9150	0.4726	0.070*
C4	0.5764 (3)	0.8349 (4)	0.3949 (4)	0.0789 (17)
H4A	0.5873	0.8700	0.3464	0.118*
H4B	0.5212	0.8506	0.4175	0.118*
H4C	0.5765	0.7729	0.3804	0.118*
C5	0.7951 (3)	0.8604 (4)	0.5021 (3)	0.0677 (14)
H5A	0.7825	0.8254	0.5511	0.081*
H5B	0.7813	0.9220	0.5146	0.081*
C6	0.8915 (3)	0.8539 (4)	0.4842 (4)	0.0879 (19)
H6A	0.9040	0.7971	0.4597	0.132*
H6B	0.9232	0.8601	0.5349	0.132*
H6C	0.9079	0.9004	0.4466	0.132*
C7	0.7465 (3)	0.7295 (3)	0.4183 (3)	0.0590 (13)
H7A	0.7085	0.7123	0.3733	0.071*
H7B	0.8051	0.7176	0.4006	0.071*
C8	0.7268 (3)	0.6716 (3)	0.4920 (3)	0.0574 (12)
C9	0.7909 (4)	0.6451 (4)	0.5460 (4)	0.0751 (15)
H9	0.8470	0.6648	0.5377	0.090*
C10	0.7728 (5)	0.5891 (4)	0.6129 (4)	0.0880 (18)
H10	0.8164	0.5715	0.6488	0.106*
C11	0.6901 (5)	0.5607 (4)	0.6247 (4)	0.0864 (18)
H11	0.6771	0.5245	0.6697	0.104*
C12	0.6270 (4)	0.5847 (4)	0.5717 (5)	0.0929 (19)
H12	0.5711	0.5642	0.5800	0.111*
C13	0.6447 (3)	0.6390 (4)	0.5060 (4)	0.0738 (15)
H13	0.6005	0.6544	0.4698	0.089*
Cl1	−0.0663 (7)	0.7414 (8)	0.2546 (8)	0.116 (3)	0.344 (11)
Cl2	0.1300 (9)	0.7070 (9)	0.3047 (8)	0.089 (3)	0.344 (11)
Cl2'	0.1493 (4)	0.6778 (5)	0.2948 (5)	0.0878 (15)	0.656 (11)
Cl3	0.0269 (6)	0.5423 (8)	0.1865 (6)	0.109 (2)	0.344 (11)
Cl4	−0.02775 (10)	0.58556 (13)	0.41086 (9)	0.0936 (6)
Cl1'	−0.0875 (3)	0.7000 (5)	0.2274 (3)	0.1154 (16)	0.656 (11)
Cl3'	0.0285 (3)	0.4954 (5)	0.2216 (4)	0.1169 (19)	0.656 (11)
Fe1	0.01578 (5)	0.62672 (6)	0.28825 (4)	0.0672 (3)
N1	0.7371 (2)	0.8292 (3)	0.4325 (2)	0.0527 (10)

	U11	U22	U33	U12	U13	U23
C1	0.065 (3)	0.081 (4)	0.053 (3)	0.003 (3)	0.013 (2)	0.000 (3)
C2	0.085 (4)	0.081 (4)	0.079 (4)	0.000 (3)	0.004 (3)	0.010 (3)
C3	0.045 (2)	0.064 (3)	0.066 (3)	0.008 (2)	0.007 (2)	−0.019 (3)
C4	0.053 (3)	0.094 (4)	0.090 (4)	0.007 (3)	−0.007 (3)	−0.019 (3)
C5	0.059 (3)	0.082 (4)	0.062 (3)	−0.009 (3)	−0.006 (2)	−0.014 (3)
C6	0.052 (3)	0.109 (5)	0.103 (5)	−0.011 (3)	−0.006 (3)	0.004 (4)
C7	0.053 (3)	0.071 (3)	0.053 (3)	0.005 (2)	0.009 (2)	−0.014 (2)
C8	0.051 (3)	0.066 (3)	0.055 (3)	0.005 (2)	0.005 (2)	−0.013 (2)
C9	0.065 (3)	0.088 (4)	0.072 (4)	0.002 (3)	0.002 (3)	0.000 (3)
C10	0.099 (5)	0.096 (5)	0.070 (4)	0.011 (4)	−0.012 (3)	0.001 (3)
C11	0.105 (5)	0.082 (4)	0.072 (4)	−0.011 (4)	0.015 (4)	0.006 (3)
C12	0.080 (4)	0.091 (5)	0.108 (5)	−0.006 (4)	0.016 (4)	0.010 (4)
C13	0.056 (3)	0.081 (4)	0.085 (4)	−0.002 (3)	0.003 (3)	0.003 (3)
Cl1	0.099 (5)	0.130 (6)	0.120 (5)	0.050 (4)	0.052 (4)	0.027 (4)
Cl2	0.095 (6)	0.112 (6)	0.060 (4)	−0.056 (4)	−0.003 (4)	0.003 (4)
Cl2'	0.079 (2)	0.110 (4)	0.075 (2)	−0.026 (2)	0.0146 (16)	0.000 (2)
Cl3	0.125 (4)	0.123 (5)	0.080 (4)	−0.015 (4)	−0.004 (4)	−0.042 (4)
Cl4	0.0898 (11)	0.1249 (14)	0.0659 (9)	−0.0371 (10)	0.0069 (8)	0.0092 (9)
Cl1'	0.096 (2)	0.153 (4)	0.097 (3)	0.017 (2)	−0.0180 (19)	0.018 (2)
Cl3'	0.103 (2)	0.142 (4)	0.105 (3)	−0.004 (2)	0.010 (2)	−0.063 (3)
Fe1	0.0567 (5)	0.0958 (7)	0.0492 (4)	−0.0014 (4)	0.0059 (3)	−0.0069 (4)
N1	0.046 (2)	0.064 (3)	0.048 (2)	0.0034 (18)	0.0056 (17)	−0.0143 (19)

C1—C2	1.503 (8)	C7—N1	1.522 (6)
C1—N1	1.528 (6)	C7—H7A	0.9700
C1—H1A	0.9700	C7—H7B	0.9700
C1—H1B	0.9700	C8—C9	1.381 (7)
C2—H2A	0.9600	C8—C13	1.384 (7)
C2—H2B	0.9600	C9—C10	1.397 (8)
C2—H2C	0.9600	C9—H9	0.9300
C3—C4	1.505 (7)	C10—C11	1.366 (9)
C3—N1	1.521 (5)	C10—H10	0.9300
C3—H3A	0.9700	C11—C12	1.350 (9)
C3—H3B	0.9700	C11—H11	0.9300
C4—H4A	0.9600	C12—C13	1.367 (8)
C4—H4B	0.9600	C12—H12	0.9300
C4—H4C	0.9600	C13—H13	0.9300
C5—N1	1.516 (6)	Cl1—Fe1	2.210 (8)
C5—C6	1.526 (7)	Cl2—Fe1	2.160 (12)
C5—H5A	0.9700	Cl3—Fe1	2.083 (7)
C5—H5B	0.9700	Fe1—Cl1'	2.178 (4)
C6—H6A	0.9600	Fe1—Cl2'	2.211 (7)
C6—H6B	0.9600	Fe1—Cl3'	2.256 (5)
C6—H6C	0.9600	Fe1—Cl4	2.1821 (17)
C7—C8	1.506 (7)
C2—C1—N1	115.3 (4)	C13—C8—C7	121.3 (5)
C2—C1—H1A	108.4	C8—C9—C10	121.2 (5)
N1—C1—H1A	108.4	C8—C9—H9	119.4
C2—C1—H1B	108.4	C10—C9—H9	119.4
N1—C1—H1B	108.4	C11—C10—C9	118.9 (6)
H1A—C1—H1B	107.5	C11—C10—H10	120.5
C1—C2—H2A	109.5	C9—C10—H10	120.5
C1—C2—H2B	109.5	C12—C11—C10	120.7 (6)
H2A—C2—H2B	109.5	C12—C11—H11	119.7
C1—C2—H2C	109.5	C10—C11—H11	119.7
H2A—C2—H2C	109.5	C11—C12—C13	120.4 (6)
H2B—C2—H2C	109.5	C11—C12—H12	119.8
C4—C3—N1	116.1 (4)	C13—C12—H12	119.8
C4—C3—H3A	108.3	C12—C13—C8	121.5 (6)
N1—C3—H3A	108.3	C12—C13—H13	119.3
C4—C3—H3B	108.3	C8—C13—H13	119.3
N1—C3—H3B	108.3	Cl3—Fe1—Cl1'	90.7 (3)
H3A—C3—H3B	107.4	Cl3—Fe1—Cl2	111.6 (4)
C3—C4—H4A	109.5	Cl1'—Fe1—Cl2	112.2 (5)
C3—C4—H4B	109.5	Cl3—Fe1—Cl4	124.7 (4)
H4A—C4—H4B	109.5	Cl1'—Fe1—Cl4	108.99 (14)
C3—C4—H4C	109.5	Cl2—Fe1—Cl4	107.5 (4)
H4A—C4—H4C	109.5	Cl3—Fe1—Cl2'	99.9 (3)
H4B—C4—H4C	109.5	Cl1'—Fe1—Cl2'	122.4 (3)
N1—C5—C6	114.9 (4)	Cl2—Fe1—Cl2'	14.5 (4)
N1—C5—H5A	108.5	Cl4—Fe1—Cl2'	110.2 (2)
C6—C5—H5A	108.5	Cl3—Fe1—Cl1	109.1 (4)
N1—C5—H5B	108.5	Cl1'—Fe1—Cl1	21.8 (3)
C6—C5—H5B	108.5	Cl2—Fe1—Cl1	93.9 (7)
H5A—C5—H5B	107.5	Cl4—Fe1—Cl1	105.4 (2)
C5—C6—H6A	109.5	Cl2'—Fe1—Cl1	106.3 (5)
C5—C6—H6B	109.5	Cl3—Fe1—Cl3'	23.7 (2)
H6A—C6—H6B	109.5	Cl1'—Fe1—Cl3'	106.90 (18)
C5—C6—H6C	109.5	Cl2—Fe1—Cl3'	118.3 (4)
H6A—C6—H6C	109.5	Cl4—Fe1—Cl3'	102.3 (2)
H6B—C6—H6C	109.5	Cl2'—Fe1—Cl3'	104.12 (19)
C8—C7—N1	115.5 (4)	Cl1—Fe1—Cl3'	127.9 (4)
C8—C7—H7A	108.4	C5—N1—C3	106.3 (3)
N1—C7—H7A	108.4	C5—N1—C7	111.0 (4)
C8—C7—H7B	108.4	C3—N1—C7	110.9 (3)
N1—C7—H7B	108.4	C5—N1—C1	111.2 (4)
H7A—C7—H7B	107.5	C3—N1—C1	110.3 (4)
C9—C8—C13	117.2 (5)	C7—N1—C1	107.1 (3)
C9—C8—C7	121.4 (5)

Table 1

Selected bond lengths (Å)

Fe1—Cl1′	2.178 (4)
Fe1—Cl2′	2.211 (7)
Fe1—Cl3′	2.256 (5)
Fe1—Cl4	2.1821 (17)