Phase transitions and twinned low-temperature structures of tetra­ethyl­ammonium tetra­chlorido­ferrate(III)

The title compound, [(C₂H₅)₄N][FeCl₄], has at room temperature a disordered structure in the high-hexa­gonal space group P6₃mc. At 230 K, the structure is merohedrally twinned in the low-hexa­gonal space group P6₃. The volume has increased by a factor of 9 with respect to the room-temperature structure. At 170 and 110 K, the structure is identical in the ortho­rhom­bic space group Pca2₁ and twinned by reticular pseudomero­hedry. The volume has doubled with respect to the room-temperature structure. All three space groups, viz. P6₃mc, P6₃ and Pca2₁, are polar and the direction of the polar axis is not affected by the twinning. In the P6₃ and Pca2₁ structures, all cations and anions are well ordered.

Computing details

For all structures, data collection: APEX2 (Bruker, 2007). Cell refinement: Peakref (Schreurs, 2013) for (Ia); Peakref (Schreurs, 2013) for (Ib), (Ic), (Id). Data reduction: Eval15 (Schreurs et al., 2010) and SADABS (Sheldrick, 2012) for (Ia); Eval15 (Schreurs et al., 2010) and SADABS (Sheldrick, 2012) for (Ib); Eval15 (Schreurs et al., 2010) and TWINABS (Sheldrick, 2012) for (Ic), (Id). Program(s) used to solve structure: coordinates from the literature (Evans et al., 1990) for (Ia); SHELXT (Sheldrick, 2014) for (Ib); SHELXD (Sheldrick, 2008) for (Ic), (Id). For all structures, program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008). Molecular graphics: PLATON (Spek, 2009) for (Ia), (Ib), (Ic); PLATON (Spek, 2009) and DRAWxtl (Finger et al., 2007) for (Id). For all structures, software used to prepare material for publication: manual editing of the SHELXL output.

Tetraethylammonium tetrachloridoferrate(III) (Ia)

Crystal data

(C8H20N)[FeCl4]	Dx = 1.412 Mg m^−3
Mr = 327.90	Mo Kα radiation, λ = 0.71073 Å
Hexagonal, P63mc	Cell parameters from 6539 reflections
a = 8.2154 (4) Å	θ = 1.5–27.4°
c = 13.1972 (8) Å	µ = 1.64 mm^−1
V = 771.38 (10) Å^3	T = 290 K
Z = 2	Block, yellow
F(000) = 338	0.43 × 0.34 × 0.10 mm

Data collection

Bruker Kappa APEXII diffractometer	630 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.018
φ and ω scans	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2012)	h = −9→10
Tmin = 0.655, Tmax = 0.746	k = −10→10
7971 measured reflections	l = −17→17
723 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.023	w = 1/[σ^2(Fo^2) + (0.0438P)^2 + 0.020P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.065	(Δ/σ)max = 0.001
S = 1.09	Δρmax = 0.17 e Å^−3
723 reflections	Δρmin = −0.12 e Å^−3
89 parameters	Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
67 restraints	Extinction coefficient: 0.029 (5)
Primary atom site location: heavy-atom method	Absolute structure: Flack x determined using 279 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.037 (8)

Special details

Experimental. loop_ _diffrn_orient_matrix_type _diffrn_orient_matrix_UB_11 _diffrn_orient_matrix_UB_12 _diffrn_orient_matrix_UB_13 _diffrn_orient_matrix_UB_21 _diffrn_orient_matrix_UB_22 _diffrn_orient_matrix_UB_23 _diffrn_orient_matrix_UB_31 _diffrn_orient_matrix_UB_32 _diffrn_orient_matrix_UB_33 'Nonius RMAT' -0.1081025 -0.1109448 -0.0330182 0.0870893 -0.0431466 -0.0249854 -0.0219582 -0.0747162 0.0634565

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.6667	0.3333	0.2509 (4)	0.0514 (9)
C1	0.506 (2)	0.1351 (13)	0.2329 (13)	0.070 (5)	0.1667
H1A	0.3914	0.1284	0.2564	0.084*	0.1667
H1B	0.4939	0.1132	0.1603	0.084*	0.1667
C2	0.521 (4)	−0.0216 (18)	0.2812 (14)	0.062 (7)	0.1667
H2A	0.4105	−0.1391	0.2655	0.093*	0.1667
H2B	0.5311	−0.0040	0.3533	0.093*	0.1667
H2C	0.6299	−0.0223	0.2559	0.093*	0.1667
C3	0.8493 (18)	0.319 (2)	0.2650 (13)	0.071 (5)	0.1667
H3A	0.8150	0.1975	0.2935	0.085*	0.1667
H3B	0.9055	0.3281	0.1991	0.085*	0.1667
C4	0.992 (3)	0.470 (3)	0.333 (3)	0.061 (10)	0.1667
H4A	1.0998	0.4551	0.3389	0.092*	0.1667
H4B	0.9377	0.4612	0.3983	0.092*	0.1667
H4C	1.0289	0.5913	0.3039	0.092*	0.1667
C5	0.643 (2)	0.422 (2)	0.3435 (8)	0.065 (5)	0.1667
H5A	0.7614	0.4816	0.3797	0.078*	0.1667
H5B	0.5514	0.3228	0.3866	0.078*	0.1667
C6	0.582 (6)	0.565 (5)	0.330 (3)	0.086 (12)	0.1667
H6A	0.5713	0.6109	0.3955	0.128*	0.1667
H6B	0.4626	0.5087	0.2966	0.128*	0.1667
H6C	0.6736	0.6682	0.2904	0.128*	0.1667
C7	0.6973 (19)	0.4544 (16)	0.1589 (7)	0.057 (4)	0.1667
H7A	0.5858	0.4649	0.1493	0.068*	0.1667
H7B	0.8007	0.5795	0.1733	0.068*	0.1667
C8	0.739 (2)	0.390 (5)	0.0602 (7)	0.077 (7)	0.1667
H8A	0.7578	0.4783	0.0078	0.115*	0.1667
H8B	0.6350	0.2687	0.0426	0.115*	0.1667
H8C	0.8503	0.3805	0.0676	0.115*	0.1667
Fe1	0.0000	0.0000	0.50819 (8)	0.0649 (3)
Cl1	0.0000	0.0000	0.34260 (12)	0.0928 (8)
Cl2	−0.14530 (8)	0.14530 (8)	0.56231 (13)	0.1007 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0534 (12)	0.0534 (12)	0.047 (2)	0.0267 (6)	0.000	0.000
C1	0.062 (8)	0.059 (8)	0.079 (10)	0.022 (6)	−0.008 (7)	−0.003 (7)
C2	0.049 (15)	0.054 (8)	0.090 (12)	0.031 (7)	0.032 (10)	0.034 (7)
C3	0.059 (8)	0.073 (8)	0.089 (11)	0.040 (7)	0.010 (8)	0.015 (9)
C4	0.084 (14)	0.03 (2)	0.089 (15)	0.045 (10)	−0.033 (11)	−0.024 (10)
C5	0.069 (11)	0.058 (10)	0.055 (6)	0.022 (9)	0.007 (5)	−0.018 (6)
C6	0.07 (2)	0.10 (3)	0.089 (18)	0.05 (2)	0.009 (14)	−0.013 (15)
C7	0.050 (9)	0.062 (6)	0.062 (6)	0.032 (5)	0.002 (5)	0.018 (5)
C8	0.100 (11)	0.089 (15)	0.053 (4)	0.055 (9)	0.003 (6)	−0.003 (9)
Fe1	0.0668 (4)	0.0668 (4)	0.0613 (5)	0.03339 (18)	0.000	0.000
Cl1	0.1090 (13)	0.1090 (13)	0.0606 (13)	0.0545 (6)	0.000	0.000
Cl2	0.1134 (7)	0.1134 (7)	0.1018 (7)	0.0767 (7)	0.0080 (3)	−0.0080 (3)

Geometric parameters (Å, º)

N1—C5	1.486 (9)	C5—C6	1.500 (14)
N1—C7	1.509 (9)	C5—H5A	0.9700
N1—C1	1.516 (10)	C5—H5B	0.9700
N1—C3	1.572 (10)	C6—H6A	0.9600
C1—C2	1.493 (13)	C6—H6B	0.9600
C1—H1A	0.9700	C6—H6C	0.9600
C1—H1B	0.9700	C7—C8	1.509 (15)
C2—H2A	0.9600	C7—H7A	0.9700
C2—H2B	0.9600	C7—H7B	0.9700
C2—H2C	0.9600	C8—H8A	0.9600
C3—C4	1.502 (13)	C8—H8B	0.9600
C3—H3A	0.9700	C8—H8C	0.9600
C3—H3B	0.9700	Fe1—Cl1	2.1853 (18)
C4—H4A	0.9600	Fe1—Cl2^i	2.1874 (12)
C4—H4B	0.9600	Fe1—Cl2^ii	2.1874 (12)
C4—H4C	0.9600	Fe1—Cl2	2.1874 (12)
C5—N1—C7	111.0 (6)	N1—C5—C6	117.8 (13)
C5—N1—C1	113.6 (9)	N1—C5—H5A	107.9
C7—N1—C1	110.5 (8)	C6—C5—H5A	107.9
C5—N1—C3	107.7 (8)	N1—C5—H5B	107.9
C7—N1—C3	107.0 (8)	C6—C5—H5B	107.9
C1—N1—C3	106.7 (7)	H5A—C5—H5B	107.2
C2—C1—N1	117.3 (11)	C5—C6—H6A	109.5
C2—C1—H1A	108.0	C5—C6—H6B	109.5
N1—C1—H1A	108.0	H6A—C6—H6B	109.5
C2—C1—H1B	108.0	C5—C6—H6C	109.5
N1—C1—H1B	108.0	H6A—C6—H6C	109.5
H1A—C1—H1B	107.2	H6B—C6—H6C	109.5
C1—C2—H2A	109.5	C8—C7—N1	117.0 (13)
C1—C2—H2B	109.5	C8—C7—H7A	108.0
H2A—C2—H2B	109.5	N1—C7—H7A	108.0
C1—C2—H2C	109.5	C8—C7—H7B	108.0
H2A—C2—H2C	109.5	N1—C7—H7B	108.0
H2B—C2—H2C	109.5	H7A—C7—H7B	107.3
C4—C3—N1	112.8 (11)	C7—C8—H8A	109.5
C4—C3—H3A	109.0	C7—C8—H8B	109.5
N1—C3—H3A	109.0	H8A—C8—H8B	109.5
C4—C3—H3B	109.0	C7—C8—H8C	109.5
N1—C3—H3B	109.0	H8A—C8—H8C	109.5
H3A—C3—H3B	107.8	H8B—C8—H8C	109.5
C3—C4—H4A	109.5	Cl1—Fe1—Cl2^i	109.06 (6)
C3—C4—H4B	109.5	Cl1—Fe1—Cl2^ii	109.06 (5)
H4A—C4—H4B	109.5	Cl2^i—Fe1—Cl2^ii	109.88 (5)
C3—C4—H4C	109.5	Cl1—Fe1—Cl2	109.06 (5)
H4A—C4—H4C	109.5	Cl2^i—Fe1—Cl2	109.88 (5)
H4B—C4—H4C	109.5	Cl2^ii—Fe1—Cl2	109.88 (5)
C5—N1—C1—C2	−88.2 (16)	C7—N1—C5—C6	22 (2)
C7—N1—C1—C2	146.3 (15)	C1—N1—C5—C6	−103 (2)
C3—N1—C1—C2	30 (2)	C3—N1—C5—C6	139 (2)
C5—N1—C3—C4	−28 (2)	C5—N1—C7—C8	175.4 (11)
C7—N1—C3—C4	91 (2)	C1—N1—C7—C8	−57.7 (14)
C1—N1—C3—C4	−150.6 (19)	C3—N1—C7—C8	58.1 (13)

Symmetry codes: (i) −x+y, −x, z; (ii) −y, x−y, z.

Tetraethylammonium tetrachloridoferrate(III) (Ib)

Crystal data

(C8H20N)[FeCl4]	Dx = 1.445 Mg m^−3
Mr = 327.90	Mo Kα radiation, λ = 0.71073 Å
Hexagonal, P63	Cell parameters from 54564 reflections
a = 24.5130 (6) Å	θ = 1.6–27.5°
c = 13.0356 (5) Å	µ = 1.68 mm^−1
V = 6783.5 (5) Å^3	T = 230 K
Z = 18	Block, yellow
F(000) = 3042	0.43 × 0.34 × 0.10 mm

Data collection

Bruker Kappa APEXII diffractometer	8945 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.026
φ and ω scans	θmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2012)	h = −27→31
Tmin = 0.660, Tmax = 0.746	k = −30→30
75629 measured reflections	l = −16→16
10366 independent reflections

Refinement

Refinement on F^2	Primary atom site location: heavy-atom method
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.083	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0386P)^2 + 1.8713P] where P = (Fo^2 + 2Fc^2)/3
10366 reflections	(Δ/σ)max = 0.019
392 parameters	Δρmax = 0.37 e Å^−3
1 restraint	Δρmin = −0.28 e Å^−3

Special details

Experimental. loop_ _diffrn_orient_matrix_type _diffrn_orient_matrix_UB_11 _diffrn_orient_matrix_UB_12 _diffrn_orient_matrix_UB_13 _diffrn_orient_matrix_UB_21 _diffrn_orient_matrix_UB_22 _diffrn_orient_matrix_UB_23 _diffrn_orient_matrix_UB_31 _diffrn_orient_matrix_UB_32 _diffrn_orient_matrix_UB_33 'Nonius RMAT' -0.0007468 0.0364094 -0.0331586 -0.0437700 -0.0289410 -0.0250654 -0.0173985 0.0074731 0.0644811

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. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.4403 (2)	0.2207 (2)	0.5833 (5)	0.0306 (13)
C11	0.3821 (3)	0.1560 (3)	0.5953 (5)	0.0551 (18)
H11A	0.3784	0.1309	0.5345	0.066*
H11B	0.3883	0.1352	0.6547	0.066*
C21	0.3212 (4)	0.1560 (3)	0.6091 (6)	0.065 (3)
H21A	0.3276	0.1893	0.6564	0.097*
H21B	0.2895	0.1157	0.6365	0.097*
H21C	0.3072	0.1631	0.5434	0.097*
C31	0.4484 (4)	0.2584 (3)	0.6780 (5)	0.0600 (17)
H31A	0.4526	0.2360	0.7369	0.072*
H31B	0.4102	0.2611	0.6883	0.072*
C41	0.5046 (3)	0.3245 (4)	0.6758 (7)	0.068 (2)
H41A	0.5431	0.3225	0.6788	0.102*
H41B	0.5027	0.3480	0.7343	0.102*
H41C	0.5039	0.3453	0.6129	0.102*
C51	0.4964 (3)	0.2122 (3)	0.5650 (5)	0.0502 (15)
H51A	0.5335	0.2536	0.5521	0.060*
H51B	0.4887	0.1867	0.5030	0.060*
C61	0.5117 (4)	0.1801 (4)	0.6554 (7)	0.079 (3)
H61A	0.5105	0.1994	0.7197	0.119*
H61B	0.5533	0.1855	0.6457	0.119*
H61C	0.4807	0.1356	0.6570	0.119*
C71	0.4329 (3)	0.2544 (3)	0.4953 (4)	0.0529 (17)
H71A	0.4717	0.2952	0.4875	0.063*
H71B	0.3986	0.2627	0.5100	0.063*
C81	0.4186 (5)	0.2170 (4)	0.3908 (6)	0.068 (2)
H81A	0.4553	0.2146	0.3698	0.101*
H81B	0.4084	0.2386	0.3384	0.101*
H81C	0.3832	0.1747	0.4001	0.101*
N2	0.2260 (2)	0.10845 (19)	0.0871 (4)	0.0263 (12)
C12	0.2195 (3)	0.1384 (3)	0.1860 (4)	0.0383 (13)
H12A	0.2171	0.1119	0.2439	0.046*
H12B	0.2577	0.1795	0.1948	0.046*
C22	0.1629 (3)	0.1479 (4)	0.1904 (5)	0.058 (2)
H22A	0.1684	0.1801	0.1416	0.088*
H22B	0.1590	0.1609	0.2590	0.088*
H22C	0.1251	0.1086	0.1735	0.088*
C32	0.2836 (2)	0.1016 (2)	0.0990 (4)	0.0308 (12)
H32A	0.2851	0.0772	0.0406	0.037*
H32B	0.2782	0.0767	0.1610	0.037*
C42	0.3474 (3)	0.1622 (3)	0.1062 (5)	0.0462 (17)
H42A	0.3521	0.1895	0.0491	0.069*
H42B	0.3808	0.1519	0.1040	0.069*
H42C	0.3498	0.1835	0.1702	0.069*
C52	0.1688 (3)	0.0441 (3)	0.0678 (5)	0.0374 (13)
H52A	0.1323	0.0496	0.0572	0.045*
H52B	0.1757	0.0272	0.0041	0.045*
C62	0.1532 (3)	−0.0035 (4)	0.1507 (4)	0.0465 (15)
H62A	0.1907	−0.0052	0.1690	0.070*
H62B	0.1209	−0.0445	0.1265	0.070*
H62C	0.1378	0.0083	0.2104	0.070*
C72	0.2332 (3)	0.1518 (2)	−0.0031 (4)	0.0332 (13)
H72A	0.1942	0.1536	−0.0088	0.040*
H72B	0.2672	0.1944	0.0132	0.040*
C82	0.2465 (3)	0.1341 (3)	−0.1035 (5)	0.0443 (16)
H82A	0.2849	0.1319	−0.0994	0.066*
H82B	0.2517	0.1653	−0.1542	0.066*
H82C	0.2118	0.0933	−0.1234	0.066*
N3	0.5579 (2)	0.1076 (2)	0.0842 (4)	0.0273 (12)
C13	0.5644 (3)	0.0495 (3)	0.0986 (5)	0.0533 (18)
H13A	0.5894	0.0548	0.1603	0.064*
H13B	0.5871	0.0455	0.0398	0.064*
C23	0.5005 (4)	−0.0111 (4)	0.1086 (5)	0.066 (3)
H23A	0.4752	−0.0051	0.1597	0.098*
H23B	0.5070	−0.0454	0.1294	0.098*
H23C	0.4789	−0.0210	0.0430	0.098*
C33	0.5298 (3)	0.1180 (3)	0.1804 (5)	0.0462 (15)
H33A	0.4894	0.0799	0.1942	0.055*
H33B	0.5579	0.1240	0.2382	0.055*
C43	0.5193 (3)	0.1730 (3)	0.1758 (7)	0.058 (2)
H43A	0.5592	0.2117	0.1853	0.086*
H43B	0.4903	0.1692	0.2295	0.086*
H43C	0.5018	0.1738	0.1095	0.086*
C53	0.6236 (2)	0.1631 (3)	0.0666 (5)	0.0461 (14)
H53A	0.6403	0.1553	0.0034	0.055*
H53B	0.6201	0.2007	0.0554	0.055*
C63	0.6709 (4)	0.1771 (4)	0.1517 (6)	0.067 (3)
H63A	0.6505	0.1716	0.2176	0.101*
H63B	0.7053	0.2201	0.1453	0.101*
H63C	0.6874	0.1485	0.1466	0.101*
C73	0.5187 (3)	0.1018 (3)	−0.0061 (4)	0.0452 (14)
H73A	0.5179	0.1412	−0.0139	0.054*
H73B	0.4754	0.0682	0.0071	0.054*
C83	0.5414 (4)	0.0874 (6)	−0.1086 (6)	0.065 (2)
H83A	0.5829	0.1220	−0.1254	0.098*
H83B	0.5121	0.0821	−0.1630	0.098*
H83C	0.5433	0.0490	−0.1013	0.098*
Fe1	0.33737 (4)	0.00273 (4)	0.33582 (7)	0.0309 (3)
Cl11	0.34314 (9)	−0.00199 (9)	0.16880 (12)	0.0561 (5)
Cl21	0.28054 (8)	0.04653 (8)	0.37520 (14)	0.0416 (4)
Cl31	0.29398 (9)	−0.09301 (9)	0.39937 (15)	0.0476 (4)
Cl41	0.43228 (9)	0.06036 (9)	0.39996 (15)	0.0495 (5)
Fe2	0.33198 (4)	0.00257 (4)	0.83363 (8)	0.0343 (3)
Cl12	0.31821 (9)	−0.00591 (9)	0.66663 (12)	0.0527 (4)
Cl22	0.23922 (8)	−0.03776 (9)	0.90686 (15)	0.0445 (4)
Cl32	0.37979 (9)	−0.04888 (9)	0.87898 (15)	0.0477 (5)
Cl42	0.38968 (9)	0.10216 (8)	0.87606 (16)	0.0490 (5)
Fe3	0.6667	0.3333	0.35736 (15)	0.0378 (5)
Cl13	0.6667	0.3333	0.1895 (3)	0.0494 (11)
Cl23	0.62767 (10)	0.23610 (10)	0.41246 (14)	0.0596 (6)
Fe4	0.0000	0.0000	0.86279 (12)	0.0346 (4)
Cl14	0.0000	0.0000	0.6938 (2)	0.0467 (8)
Cl24	0.06233 (8)	0.09662 (9)	0.91781 (13)	0.0459 (4)
Fe5	0.6667	0.3333	0.85790 (15)	0.0395 (5)
Cl15	0.6667	0.3333	0.6898 (3)	0.0532 (11)
Cl25	0.56964 (10)	0.27434 (10)	0.91285 (14)	0.0594 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.036 (3)	0.024 (3)	0.031 (3)	0.014 (2)	0.007 (2)	0.006 (2)
C11	0.048 (4)	0.042 (4)	0.053 (4)	0.006 (3)	0.000 (3)	0.000 (3)
C21	0.041 (5)	0.055 (5)	0.073 (6)	0.005 (3)	0.013 (4)	0.007 (4)
C31	0.076 (5)	0.067 (4)	0.045 (3)	0.042 (4)	−0.006 (4)	−0.023 (3)
C41	0.050 (4)	0.046 (4)	0.098 (6)	0.017 (4)	0.000 (4)	−0.027 (5)
C51	0.043 (4)	0.046 (4)	0.065 (4)	0.025 (3)	0.012 (3)	0.000 (3)
C61	0.092 (7)	0.089 (7)	0.090 (6)	0.070 (6)	−0.026 (5)	0.007 (5)
C71	0.064 (5)	0.042 (4)	0.043 (3)	0.020 (3)	−0.002 (3)	0.006 (3)
C81	0.095 (8)	0.075 (6)	0.032 (4)	0.042 (6)	−0.003 (4)	−0.007 (4)
N2	0.030 (3)	0.023 (2)	0.025 (2)	0.013 (2)	−0.001 (2)	−0.006 (2)
C12	0.036 (3)	0.039 (3)	0.035 (3)	0.016 (3)	−0.008 (3)	−0.008 (3)
C22	0.068 (5)	0.062 (5)	0.050 (3)	0.036 (4)	0.007 (3)	−0.006 (3)
C32	0.024 (3)	0.029 (3)	0.040 (3)	0.013 (2)	−0.012 (2)	−0.002 (2)
C42	0.036 (4)	0.036 (3)	0.058 (4)	0.012 (3)	−0.008 (3)	−0.003 (3)
C52	0.033 (3)	0.035 (3)	0.040 (3)	0.014 (3)	−0.001 (3)	0.000 (3)
C62	0.033 (4)	0.040 (3)	0.063 (4)	0.016 (3)	−0.001 (3)	0.001 (4)
C72	0.030 (3)	0.023 (3)	0.041 (3)	0.009 (2)	−0.010 (3)	−0.006 (2)
C82	0.058 (4)	0.034 (3)	0.041 (3)	0.023 (3)	−0.003 (3)	0.007 (3)
N3	0.031 (3)	0.024 (3)	0.028 (3)	0.015 (2)	−0.002 (2)	0.001 (2)
C13	0.079 (5)	0.069 (5)	0.038 (3)	0.058 (4)	−0.010 (3)	−0.007 (3)
C23	0.100 (7)	0.028 (4)	0.069 (6)	0.031 (4)	0.003 (4)	0.011 (4)
C33	0.051 (4)	0.061 (4)	0.037 (3)	0.035 (3)	0.013 (3)	−0.006 (3)
C43	0.043 (4)	0.044 (4)	0.089 (5)	0.025 (3)	0.005 (4)	−0.018 (4)
C53	0.028 (3)	0.041 (3)	0.061 (4)	0.011 (3)	0.009 (3)	0.007 (3)
C63	0.040 (4)	0.081 (6)	0.057 (4)	0.013 (4)	−0.018 (4)	−0.002 (4)
C73	0.044 (4)	0.059 (4)	0.042 (3)	0.033 (3)	−0.011 (3)	0.000 (3)
C83	0.067 (5)	0.109 (7)	0.032 (4)	0.053 (5)	−0.004 (3)	−0.013 (5)
Fe1	0.0328 (5)	0.0332 (5)	0.0268 (4)	0.0165 (4)	−0.0002 (4)	0.0014 (4)
Cl11	0.0794 (12)	0.0780 (13)	0.0277 (8)	0.0518 (12)	0.0004 (7)	−0.0016 (8)
Cl21	0.0432 (10)	0.0404 (9)	0.0459 (9)	0.0243 (8)	0.0004 (7)	−0.0003 (7)
Cl31	0.0504 (9)	0.0358 (9)	0.0573 (11)	0.0221 (8)	0.0105 (8)	0.0082 (7)
Cl41	0.0374 (9)	0.0486 (10)	0.0571 (10)	0.0176 (8)	−0.0069 (8)	0.0024 (9)
Fe2	0.0337 (6)	0.0336 (5)	0.0368 (5)	0.0177 (4)	0.0006 (3)	−0.0005 (4)
Cl12	0.0534 (9)	0.0697 (12)	0.0363 (8)	0.0318 (8)	0.0007 (7)	0.0003 (8)
Cl22	0.0379 (9)	0.0491 (10)	0.0438 (8)	0.0198 (8)	0.0093 (8)	0.0003 (8)
Cl32	0.0459 (10)	0.0447 (9)	0.0596 (11)	0.0279 (8)	−0.0059 (8)	0.0020 (8)
Cl42	0.0452 (10)	0.0340 (9)	0.0617 (11)	0.0151 (8)	−0.0001 (8)	−0.0057 (8)
Fe3	0.0386 (8)	0.0386 (8)	0.0361 (13)	0.0193 (4)	0.000	0.000
Cl13	0.0560 (16)	0.0560 (16)	0.036 (2)	0.0280 (8)	0.000	0.000
Cl23	0.0746 (13)	0.0447 (10)	0.0542 (11)	0.0260 (10)	0.0034 (10)	0.0066 (9)
Fe4	0.0342 (5)	0.0342 (5)	0.0354 (10)	0.0171 (3)	0.000	0.000
Cl14	0.0519 (11)	0.0519 (11)	0.0364 (16)	0.0260 (6)	0.000	0.000
Cl24	0.0437 (10)	0.0397 (9)	0.0483 (9)	0.0164 (8)	−0.0039 (9)	−0.0083 (8)
Fe5	0.0412 (8)	0.0412 (8)	0.0360 (12)	0.0206 (4)	0.000	0.000
Cl15	0.0615 (16)	0.0615 (16)	0.037 (2)	0.0308 (8)	0.000	0.000
Cl25	0.0461 (9)	0.0654 (13)	0.0559 (11)	0.0197 (9)	0.0096 (9)	0.0039 (10)

Geometric parameters (Å, º)

N1—C71	1.476 (8)	C72—H72B	0.9800
N1—C31	1.494 (8)	C82—H82A	0.9700
N1—C51	1.511 (7)	C82—H82B	0.9700
N1—C11	1.521 (7)	C82—H82C	0.9700
C11—C21	1.505 (10)	N3—C73	1.481 (7)
C11—H11A	0.9800	N3—C33	1.512 (7)
C11—H11B	0.9800	N3—C53	1.518 (7)
C21—H21A	0.9700	N3—C13	1.523 (7)
C21—H21B	0.9700	C13—C23	1.532 (10)
C21—H21C	0.9700	C13—H13A	0.9800
C31—C41	1.514 (10)	C13—H13B	0.9800
C31—H31A	0.9800	C23—H23A	0.9700
C31—H31B	0.9800	C23—H23B	0.9700
C41—H41A	0.9700	C23—H23C	0.9700
C41—H41B	0.9700	C33—C43	1.495 (9)
C41—H41C	0.9700	C33—H33A	0.9800
C51—C61	1.562 (10)	C33—H33B	0.9800
C51—H51A	0.9800	C43—H43A	0.9700
C51—H51B	0.9800	C43—H43B	0.9700
C61—H61A	0.9700	C43—H43C	0.9700
C61—H61B	0.9700	C53—C63	1.515 (9)
C61—H61C	0.9700	C53—H53A	0.9800
C71—C81	1.581 (9)	C53—H53B	0.9800
C71—H71A	0.9800	C63—H63A	0.9700
C71—H71B	0.9800	C63—H63B	0.9700
C81—H81A	0.9700	C63—H63C	0.9700
C81—H81B	0.9700	C73—C83	1.555 (9)
C81—H81C	0.9700	C73—H73A	0.9800
N2—C32	1.511 (6)	C73—H73B	0.9800
N2—C52	1.518 (6)	C83—H83A	0.9700
N2—C12	1.531 (7)	C83—H83B	0.9700
N2—C72	1.536 (7)	C83—H83C	0.9700
C12—C22	1.519 (9)	Fe1—Cl11	2.1886 (17)
C12—H12A	0.9800	Fe1—Cl41	2.196 (2)
C12—H12B	0.9800	Fe1—Cl31	2.198 (2)
C22—H22A	0.9700	Fe1—Cl21	2.2026 (18)
C22—H22B	0.9700	Fe2—Cl32	2.189 (2)
C22—H22C	0.9700	Fe2—Cl22	2.1933 (18)
C32—C42	1.528 (8)	Fe2—Cl42	2.1940 (19)
C32—H32A	0.9800	Fe2—Cl12	2.1968 (19)
C32—H32B	0.9800	Fe3—Cl13	2.188 (4)
C42—H42A	0.9700	Fe3—Cl23	2.198 (2)
C42—H42B	0.9700	Fe3—Cl23^i	2.198 (2)
C42—H42C	0.9700	Fe3—Cl23^ii	2.198 (2)
C52—C62	1.493 (8)	Fe4—Cl24	2.1999 (19)
C52—H52A	0.9800	Fe4—Cl24^iii	2.1999 (19)
C52—H52B	0.9800	Fe4—Cl24^iv	2.1999 (19)
C62—H62A	0.9700	Fe4—Cl14	2.202 (4)
C62—H62B	0.9700	Fe5—Cl15	2.191 (4)
C62—H62C	0.9700	Fe5—Cl25^i	2.196 (2)
C72—C82	1.467 (8)	Fe5—Cl25^ii	2.196 (2)
C72—H72A	0.9800	Fe5—Cl25	2.196 (2)
C71—N1—C31	108.2 (4)	C82—C72—N2	116.3 (4)
C71—N1—C51	109.3 (5)	C82—C72—H72A	108.2
C31—N1—C51	111.6 (5)	N2—C72—H72A	108.2
C71—N1—C11	110.5 (5)	C82—C72—H72B	108.2
C31—N1—C11	108.9 (5)	N2—C72—H72B	108.2
C51—N1—C11	108.4 (4)	H72A—C72—H72B	107.4
C21—C11—N1	115.2 (5)	C72—C82—H82A	109.5
C21—C11—H11A	108.5	C72—C82—H82B	109.5
N1—C11—H11A	108.5	H82A—C82—H82B	109.5
C21—C11—H11B	108.5	C72—C82—H82C	109.5
N1—C11—H11B	108.5	H82A—C82—H82C	109.5
H11A—C11—H11B	107.5	H82B—C82—H82C	109.5
C11—C21—H21A	109.5	C73—N3—C33	110.3 (4)
C11—C21—H21B	109.5	C73—N3—C53	108.2 (5)
H21A—C21—H21B	109.5	C33—N3—C53	110.1 (5)
C11—C21—H21C	109.5	C73—N3—C13	112.0 (5)
H21A—C21—H21C	109.5	C33—N3—C13	109.0 (5)
H21B—C21—H21C	109.5	C53—N3—C13	107.2 (4)
N1—C31—C41	114.5 (6)	N3—C13—C23	112.5 (5)
N1—C31—H31A	108.6	N3—C13—H13A	109.1
C41—C31—H31A	108.6	C23—C13—H13A	109.1
N1—C31—H31B	108.6	N3—C13—H13B	109.1
C41—C31—H31B	108.6	C23—C13—H13B	109.1
H31A—C31—H31B	107.6	H13A—C13—H13B	107.8
C31—C41—H41A	109.5	C13—C23—H23A	109.5
C31—C41—H41B	109.5	C13—C23—H23B	109.5
H41A—C41—H41B	109.5	H23A—C23—H23B	109.5
C31—C41—H41C	109.5	C13—C23—H23C	109.5
H41A—C41—H41C	109.5	H23A—C23—H23C	109.5
H41B—C41—H41C	109.5	H23B—C23—H23C	109.5
N1—C51—C61	114.5 (6)	C43—C33—N3	114.6 (6)
N1—C51—H51A	108.6	C43—C33—H33A	108.6
C61—C51—H51A	108.6	N3—C33—H33A	108.6
N1—C51—H51B	108.6	C43—C33—H33B	108.6
C61—C51—H51B	108.6	N3—C33—H33B	108.6
H51A—C51—H51B	107.6	H33A—C33—H33B	107.6
C51—C61—H61A	109.5	C33—C43—H43A	109.5
C51—C61—H61B	109.5	C33—C43—H43B	109.5
H61A—C61—H61B	109.5	H43A—C43—H43B	109.5
C51—C61—H61C	109.5	C33—C43—H43C	109.5
H61A—C61—H61C	109.5	H43A—C43—H43C	109.5
H61B—C61—H61C	109.5	H43B—C43—H43C	109.5
N1—C71—C81	113.5 (5)	C63—C53—N3	116.2 (5)
N1—C71—H71A	108.9	C63—C53—H53A	108.2
C81—C71—H71A	108.9	N3—C53—H53A	108.2
N1—C71—H71B	108.9	C63—C53—H53B	108.2
C81—C71—H71B	108.9	N3—C53—H53B	108.2
H71A—C71—H71B	107.7	H53A—C53—H53B	107.4
C71—C81—H81A	109.5	C53—C63—H63A	109.5
C71—C81—H81B	109.5	C53—C63—H63B	109.5
H81A—C81—H81B	109.5	H63A—C63—H63B	109.5
C71—C81—H81C	109.5	C53—C63—H63C	109.5
H81A—C81—H81C	109.5	H63A—C63—H63C	109.5
H81B—C81—H81C	109.5	H63B—C63—H63C	109.5
C32—N2—C52	109.3 (4)	N3—C73—C83	114.6 (5)
C32—N2—C12	107.1 (5)	N3—C73—H73A	108.6
C52—N2—C12	112.0 (5)	C83—C73—H73A	108.6
C32—N2—C72	111.5 (4)	N3—C73—H73B	108.6
C52—N2—C72	108.6 (4)	C83—C73—H73B	108.6
C12—N2—C72	108.4 (4)	H73A—C73—H73B	107.6
C22—C12—N2	115.3 (5)	C73—C83—H83A	109.5
C22—C12—H12A	108.4	C73—C83—H83B	109.5
N2—C12—H12A	108.4	H83A—C83—H83B	109.5
C22—C12—H12B	108.4	C73—C83—H83C	109.5
N2—C12—H12B	108.4	H83A—C83—H83C	109.5
H12A—C12—H12B	107.5	H83B—C83—H83C	109.5
C12—C22—H22A	109.5	Cl11—Fe1—Cl41	109.70 (9)
C12—C22—H22B	109.5	Cl11—Fe1—Cl31	109.15 (8)
H22A—C22—H22B	109.5	Cl41—Fe1—Cl31	109.56 (8)
C12—C22—H22C	109.5	Cl11—Fe1—Cl21	109.33 (8)
H22A—C22—H22C	109.5	Cl41—Fe1—Cl21	108.82 (8)
H22B—C22—H22C	109.5	Cl31—Fe1—Cl21	110.26 (7)
N2—C32—C42	117.3 (5)	Cl32—Fe2—Cl22	110.84 (8)
N2—C32—H32A	108.0	Cl32—Fe2—Cl42	109.88 (7)
C42—C32—H32A	108.0	Cl22—Fe2—Cl42	109.76 (8)
N2—C32—H32B	108.0	Cl32—Fe2—Cl12	108.32 (8)
C42—C32—H32B	108.0	Cl22—Fe2—Cl12	108.24 (8)
H32A—C32—H32B	107.2	Cl42—Fe2—Cl12	109.76 (8)
C32—C42—H42A	109.5	Cl13—Fe3—Cl23	109.07 (7)
C32—C42—H42B	109.5	Cl13—Fe3—Cl23^i	109.07 (7)
H42A—C42—H42B	109.5	Cl23—Fe3—Cl23^i	109.87 (7)
C32—C42—H42C	109.5	Cl13—Fe3—Cl23^ii	109.07 (7)
H42A—C42—H42C	109.5	Cl23—Fe3—Cl23^ii	109.87 (7)
H42B—C42—H42C	109.5	Cl23^i—Fe3—Cl23^ii	109.87 (7)
C62—C52—N2	115.8 (5)	Cl24—Fe4—Cl24^iii	109.91 (6)
C62—C52—H52A	108.3	Cl24—Fe4—Cl24^iv	109.91 (6)
N2—C52—H52A	108.3	Cl24^iii—Fe4—Cl24^iv	109.91 (6)
C62—C52—H52B	108.3	Cl24—Fe4—Cl14	109.03 (6)
N2—C52—H52B	108.3	Cl24^iii—Fe4—Cl14	109.03 (6)
H52A—C52—H52B	107.4	Cl24^iv—Fe4—Cl14	109.03 (6)
C52—C62—H62A	109.5	Cl15—Fe5—Cl25^i	109.04 (8)
C52—C62—H62B	109.5	Cl15—Fe5—Cl25^ii	109.04 (8)
H62A—C62—H62B	109.5	Cl25^i—Fe5—Cl25^ii	109.90 (7)
C52—C62—H62C	109.5	Cl15—Fe5—Cl25	109.04 (8)
H62A—C62—H62C	109.5	Cl25^i—Fe5—Cl25	109.90 (7)
H62B—C62—H62C	109.5	Cl25^ii—Fe5—Cl25	109.90 (7)
C71—N1—C11—C21	−57.5 (8)	C32—N2—C52—C62	60.7 (7)
C31—N1—C11—C21	61.2 (8)	C12—N2—C52—C62	−57.9 (7)
C51—N1—C11—C21	−177.2 (6)	C72—N2—C52—C62	−177.5 (5)
C71—N1—C31—C41	−59.3 (8)	C32—N2—C72—C82	56.3 (6)
C51—N1—C31—C41	60.9 (7)	C52—N2—C72—C82	−64.2 (6)
C11—N1—C31—C41	−179.4 (6)	C12—N2—C72—C82	174.0 (5)
C71—N1—C51—C61	176.9 (6)	C73—N3—C13—C23	−56.9 (7)
C31—N1—C51—C61	57.4 (7)	C33—N3—C13—C23	65.5 (6)
C11—N1—C51—C61	−62.6 (8)	C53—N3—C13—C23	−175.4 (5)
C31—N1—C71—C81	−175.4 (7)	C73—N3—C33—C43	−55.2 (7)
C51—N1—C71—C81	62.9 (8)	C53—N3—C33—C43	64.1 (6)
C11—N1—C71—C81	−56.3 (8)	C13—N3—C33—C43	−178.5 (6)
C32—N2—C12—C22	−178.5 (5)	C73—N3—C53—C63	179.5 (6)
C52—N2—C12—C22	−58.7 (7)	C33—N3—C53—C63	58.9 (7)
C72—N2—C12—C22	61.1 (6)	C13—N3—C53—C63	−59.5 (7)
C52—N2—C32—C42	172.9 (5)	C33—N3—C73—C83	−176.9 (7)
C12—N2—C32—C42	−65.6 (6)	C53—N3—C73—C83	62.7 (8)
C72—N2—C32—C42	52.8 (7)	C13—N3—C73—C83	−55.3 (8)

Symmetry codes: (i) −y+1, x−y, z; (ii) −x+y+1, −x+1, z; (iii) −y, x−y, z; (iv) −x+y, −x, z.

Tetraethylammonium tetrachloridoferrate(III) (Ic)

Crystal data

(C8H20N)[FeCl4]	Dx = 1.481 Mg m^−3
Mr = 327.90	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 6968 reflections
a = 14.0182 (8) Å	θ = 2.2–27.5°
b = 8.1493 (5) Å	µ = 1.72 mm^−1
c = 12.8767 (8) Å	T = 170 K
V = 1471.01 (15) Å^3	Block, yellow
Z = 4	0.43 × 0.34 × 0.10 mm
F(000) = 676

Data collection

Bruker Kappa APEXII diffractometer	7535 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.028
φ and ω scans	θmax = 27.6°, θmin = 2.5°
Absorption correction: multi-scan (TWINABS; Sheldrick, 2012)	h = −18→18
Tmin = 0.639, Tmax = 0.746	k = −10→10
32765 measured reflections	l = −16→16
7746 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.014	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.034	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0132P)^2 + 0.0367P] where P = (Fo^2 + 2Fc^2)/3
7746 reflections	(Δ/σ)max < 0.001
133 parameters	Δρmax = 0.12 e Å^−3
1 restraint	Δρmin = −0.27 e Å^−3

Special details

Experimental. loop_ _diffrn_orient_matrix_type _diffrn_orient_matrix_UB_11 _diffrn_orient_matrix_UB_12 _diffrn_orient_matrix_UB_13 _diffrn_orient_matrix_UB_21 _diffrn_orient_matrix_UB_22 _diffrn_orient_matrix_UB_23 _diffrn_orient_matrix_UB_31 _diffrn_orient_matrix_UB_32 _diffrn_orient_matrix_UB_33 'Nonius RMAT' -0.0552117 0.0570192 0.0335576 0.0438346 0.0881353 0.0255620 -0.0112121 0.0637923 -0.0653109 'Nonius RMAT' 0.0010845 0.1107900 0.0335563 0.0662764 -0.0212420 0.0255569 0.0264909 0.0486090 -0.0653135 'Nonius RMAT' 0.0562913 0.0537792 0.0335726 0.0224478 -0.1093919 0.0255528 0.0377212 -0.0151557 -0.0653067

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. Refined as a 3-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.41494 (16)	0.7816 (2)	0.48126 (18)	0.0184 (4)
C1	0.46102 (16)	0.6995 (3)	0.38735 (17)	0.0225 (4)
H1A	0.4200	0.7196	0.3261	0.027*
H1B	0.5231	0.7536	0.3741	0.027*
C2	0.47780 (17)	0.5180 (3)	0.39615 (19)	0.0293 (5)
H2A	0.5203	0.4961	0.4550	0.044*
H2B	0.5073	0.4776	0.3321	0.044*
H2C	0.4168	0.4620	0.4071	0.044*
C3	0.31528 (16)	0.7135 (3)	0.5002 (2)	0.0245 (5)
H3A	0.3205	0.5939	0.5123	0.029*
H3B	0.2897	0.7635	0.5645	0.029*
C4	0.2441 (3)	0.7420 (3)	0.4132 (4)	0.0372 (10)
H4A	0.2327	0.8600	0.4055	0.056*
H4B	0.1840	0.6866	0.4299	0.056*
H4C	0.2698	0.6978	0.3482	0.056*
C5	0.40883 (13)	0.9645 (2)	0.46156 (18)	0.0224 (4)
H5A	0.3753	0.9823	0.3948	0.027*
H5B	0.3694	1.0145	0.5170	0.027*
C6	0.50356 (15)	1.0537 (3)	0.45750 (19)	0.0290 (5)
H6A	0.5377	1.0374	0.5231	0.044*
H6B	0.4924	1.1712	0.4466	0.044*
H6C	0.5419	1.0102	0.4001	0.044*
C7	0.4758 (2)	0.7440 (2)	0.5762 (2)	0.0236 (6)
H7A	0.4742	0.6241	0.5886	0.028*
H7B	0.5427	0.7742	0.5604	0.028*
C8	0.44635 (17)	0.8304 (3)	0.67549 (18)	0.0325 (5)
H8A	0.4501	0.9494	0.6654	0.049*
H8B	0.4892	0.7978	0.7320	0.049*
H8C	0.3807	0.7998	0.6932	0.049*
Fe1	0.24092 (2)	0.27786 (4)	0.22244 (3)	0.02156 (8)
Cl1	0.23050 (5)	0.27656 (9)	0.39273 (5)	0.03161 (15)
Cl2	0.30246 (4)	0.04137 (8)	0.17363 (5)	0.03122 (13)
Cl3	0.09746 (4)	0.30823 (8)	0.15619 (5)	0.02864 (12)
Cl4	0.33085 (4)	0.48244 (7)	0.16997 (5)	0.02879 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0172 (9)	0.0192 (7)	0.0187 (10)	0.0009 (9)	0.0009 (8)	0.0020 (9)
C1	0.0224 (11)	0.0245 (12)	0.0206 (11)	0.0022 (10)	0.0032 (9)	−0.0034 (11)
C2	0.0339 (12)	0.0241 (13)	0.0299 (12)	0.0044 (10)	0.0034 (10)	−0.0040 (9)
C3	0.0178 (11)	0.0259 (10)	0.0299 (13)	−0.0024 (10)	0.0054 (10)	0.0006 (11)
C4	0.0213 (16)	0.044 (2)	0.046 (3)	−0.0027 (10)	−0.0035 (12)	−0.0027 (11)
C5	0.0278 (10)	0.0173 (9)	0.0222 (10)	0.0027 (8)	−0.0001 (9)	0.0040 (9)
C6	0.0339 (12)	0.0219 (11)	0.0314 (12)	−0.0048 (9)	0.0023 (11)	0.0026 (11)
C7	0.0242 (17)	0.0263 (18)	0.0202 (14)	0.0035 (8)	−0.0030 (11)	0.0056 (7)
C8	0.0401 (12)	0.0347 (14)	0.0227 (12)	0.0053 (10)	−0.0017 (10)	0.0020 (11)
Fe1	0.02122 (17)	0.02333 (14)	0.02012 (15)	0.00090 (12)	−0.00028 (16)	−0.0004 (2)
Cl1	0.0327 (4)	0.0415 (4)	0.0206 (3)	0.0014 (2)	−0.0002 (3)	0.0020 (3)
Cl2	0.0304 (3)	0.0252 (3)	0.0380 (3)	0.0024 (2)	0.0019 (3)	−0.0045 (3)
Cl3	0.0249 (3)	0.0325 (3)	0.0285 (3)	0.0019 (2)	−0.0044 (2)	0.0007 (3)
Cl4	0.0292 (2)	0.0274 (3)	0.0297 (3)	−0.0028 (2)	0.0012 (3)	0.0010 (3)

Geometric parameters (Å, º)

N1—C5	1.515 (3)	C5—C6	1.515 (3)
N1—C7	1.522 (4)	C5—H5A	0.9900
N1—C3	1.523 (3)	C5—H5B	0.9900
N1—C1	1.525 (3)	C6—H6A	0.9800
C1—C2	1.502 (4)	C6—H6B	0.9800
C1—H1A	0.9900	C6—H6C	0.9800
C1—H1B	0.9900	C7—C8	1.517 (4)
C2—H2A	0.9800	C7—H7A	0.9900
C2—H2B	0.9800	C7—H7B	0.9900
C2—H2C	0.9800	C8—H8A	0.9800
C3—C4	1.517 (5)	C8—H8B	0.9800
C3—H3A	0.9900	C8—H8C	0.9800
C3—H3B	0.9900	Fe1—Cl4	2.1966 (7)
C4—H4A	0.9800	Fe1—Cl1	2.1977 (7)
C4—H4B	0.9800	Fe1—Cl3	2.1985 (6)
C4—H4C	0.9800	Fe1—Cl2	2.2030 (7)
C5—N1—C7	111.36 (17)	C6—C5—N1	115.37 (17)
C5—N1—C3	109.48 (17)	C6—C5—H5A	108.4
C7—N1—C3	108.2 (2)	N1—C5—H5A	108.4
C5—N1—C1	108.83 (18)	C6—C5—H5B	108.4
C7—N1—C1	108.13 (19)	N1—C5—H5B	108.4
C3—N1—C1	110.82 (18)	H5A—C5—H5B	107.5
C2—C1—N1	116.00 (19)	C5—C6—H6A	109.5
C2—C1—H1A	108.3	C5—C6—H6B	109.5
N1—C1—H1A	108.3	H6A—C6—H6B	109.5
C2—C1—H1B	108.3	C5—C6—H6C	109.5
N1—C1—H1B	108.3	H6A—C6—H6C	109.5
H1A—C1—H1B	107.4	H6B—C6—H6C	109.5
C1—C2—H2A	109.5	C8—C7—N1	115.5 (2)
C1—C2—H2B	109.5	C8—C7—H7A	108.4
H2A—C2—H2B	109.5	N1—C7—H7A	108.4
C1—C2—H2C	109.5	C8—C7—H7B	108.4
H2A—C2—H2C	109.5	N1—C7—H7B	108.4
H2B—C2—H2C	109.5	H7A—C7—H7B	107.5
C4—C3—N1	115.4 (2)	C7—C8—H8A	109.5
C4—C3—H3A	108.4	C7—C8—H8B	109.5
N1—C3—H3A	108.4	H8A—C8—H8B	109.5
C4—C3—H3B	108.4	C7—C8—H8C	109.5
N1—C3—H3B	108.4	H8A—C8—H8C	109.5
H3A—C3—H3B	107.5	H8B—C8—H8C	109.5
C3—C4—H4A	109.5	Cl4—Fe1—Cl1	110.41 (3)
C3—C4—H4B	109.5	Cl4—Fe1—Cl3	108.67 (3)
H4A—C4—H4B	109.5	Cl1—Fe1—Cl3	109.08 (3)
C3—C4—H4C	109.5	Cl4—Fe1—Cl2	110.58 (3)
H4A—C4—H4C	109.5	Cl1—Fe1—Cl2	107.85 (3)
H4B—C4—H4C	109.5	Cl3—Fe1—Cl2	110.24 (3)
C5—N1—C1—C2	176.68 (18)	C7—N1—C5—C6	51.5 (3)
C7—N1—C1—C2	55.6 (2)	C3—N1—C5—C6	171.2 (2)
C3—N1—C1—C2	−62.9 (3)	C1—N1—C5—C6	−67.6 (2)
C5—N1—C3—C4	57.7 (3)	C5—N1—C7—C8	54.5 (3)
C7—N1—C3—C4	179.3 (2)	C3—N1—C7—C8	−65.9 (2)
C1—N1—C3—C4	−62.3 (3)	C1—N1—C7—C8	174.0 (2)

Tetraethylammonium tetrachloridoferrate(III) (Id)

Crystal data

(C8H20N)[FeCl4]	Dx = 1.497 Mg m^−3
Mr = 327.90	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 10389 reflections
a = 13.9816 (6) Å	θ = 2.2–27.5°
b = 8.1243 (3) Å	µ = 1.74 mm^−1
c = 12.8097 (6) Å	T = 110 K
V = 1455.06 (11) Å^3	Block, yellow
Z = 4	0.43 × 0.34 × 0.10 mm
F(000) = 676

Data collection

Bruker Kappa APEXII diffractometer	7776 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.028
φ and ω scans	θmax = 27.6°, θmin = 2.5°
Absorption correction: multi-scan (TWINABS; Sheldrick, 2012)	h = −18→18
Tmin = 0.655, Tmax = 0.746	k = −10→10
49619 measured reflections	l = −16→16
7924 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.012	Hydrogen site location: difference Fourier map
wR(F^2) = 0.030	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0121P)^2 + 0.0465P] where P = (Fo^2 + 2Fc^2)/3
7924 reflections	(Δ/σ)max < 0.001
133 parameters	Δρmax = 0.12 e Å^−3
1 restraint	Δρmin = −0.32 e Å^−3

Special details

Experimental. loop_ _diffrn_orient_matrix_type _diffrn_orient_matrix_UB_11 _diffrn_orient_matrix_UB_12 _diffrn_orient_matrix_UB_13 _diffrn_orient_matrix_UB_21 _diffrn_orient_matrix_UB_22 _diffrn_orient_matrix_UB_23 _diffrn_orient_matrix_UB_31 _diffrn_orient_matrix_UB_32 _diffrn_orient_matrix_UB_33 'Nonius RMAT' -0.0550213 0.0579395 0.0339429 0.0444204 0.0879475 0.0254721 -0.0112145 0.0640910 -0.0656385 'Nonius RMAT' 0.0016187 0.1110194 0.0339428 0.0664469 -0.0222439 0.0254671 0.0266171 0.0487782 -0.0656404 'Nonius RMAT' 0.0566363 0.0530991 0.0339597 0.0220348 -0.1102092 0.0254684 0.0378561 -0.0152918 -0.0656312

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. Refined as a 3-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.41526 (14)	0.7829 (2)	0.48117 (16)	0.0114 (3)
C1	0.46138 (14)	0.7009 (3)	0.38642 (15)	0.0145 (4)
H1A	0.4201	0.7209	0.3249	0.017*
H1B	0.5236	0.7552	0.3730	0.017*
C2	0.47826 (15)	0.5183 (3)	0.39556 (16)	0.0188 (4)
H2A	0.5217	0.4966	0.4540	0.028*
H2B	0.5069	0.4772	0.3308	0.028*
H2C	0.4172	0.4622	0.4079	0.028*
C3	0.31523 (15)	0.7143 (3)	0.50026 (17)	0.0157 (4)
H3A	0.3205	0.5943	0.5122	0.019*
H3B	0.2897	0.7642	0.5650	0.019*
C4	0.2438 (2)	0.7432 (2)	0.4133 (3)	0.0237 (7)
H4A	0.2336	0.8617	0.4044	0.036*
H4B	0.1830	0.6899	0.4310	0.036*
H4C	0.2686	0.6965	0.3481	0.036*
C5	0.40905 (12)	0.9664 (2)	0.46133 (16)	0.0143 (4)
H5A	0.3692	1.0165	0.5168	0.017*
H5B	0.3758	0.9841	0.3941	0.017*
C6	0.50418 (13)	1.0561 (2)	0.45783 (16)	0.0184 (4)
H6A	0.5378	1.0405	0.5242	0.028*
H6B	0.4930	1.1738	0.4463	0.028*
H6C	0.5431	1.0119	0.4008	0.028*
C7	0.4765 (2)	0.7451 (2)	0.5765 (2)	0.0152 (5)
H7A	0.4749	0.6249	0.5890	0.018*
H7B	0.5435	0.7754	0.5605	0.018*
C8	0.44684 (15)	0.8322 (3)	0.67645 (15)	0.0205 (4)
H8A	0.4495	0.9515	0.6659	0.031*
H8B	0.4904	0.8011	0.7330	0.031*
H8C	0.3814	0.8000	0.6949	0.031*
Fe1	0.24106 (2)	0.27936 (4)	0.22245 (3)	0.01356 (7)
Cl1	0.23031 (4)	0.27868 (8)	0.39388 (4)	0.02016 (12)
Cl2	0.30236 (3)	0.04105 (7)	0.17389 (4)	0.01970 (10)
Cl3	0.09726 (3)	0.31002 (6)	0.15535 (4)	0.01782 (10)
Cl4	0.33172 (3)	0.48432 (6)	0.16960 (4)	0.01817 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0105 (8)	0.0126 (7)	0.0112 (8)	0.0005 (8)	0.0000 (7)	0.0015 (8)
C1	0.0150 (9)	0.0162 (11)	0.0122 (9)	0.0009 (8)	0.0022 (7)	−0.0026 (9)
C2	0.0220 (10)	0.0165 (11)	0.0179 (9)	0.0023 (8)	0.0021 (8)	−0.0022 (8)
C3	0.0118 (9)	0.0162 (8)	0.0190 (10)	−0.0016 (9)	0.0037 (8)	0.0004 (9)
C4	0.0140 (13)	0.0274 (15)	0.030 (2)	−0.0021 (8)	−0.0015 (10)	−0.0005 (8)
C5	0.0188 (9)	0.0103 (8)	0.0138 (9)	0.0017 (7)	0.0004 (7)	0.0026 (8)
C6	0.0218 (10)	0.0146 (9)	0.0187 (10)	−0.0032 (8)	0.0005 (8)	0.0010 (9)
C7	0.0150 (14)	0.0182 (16)	0.0123 (11)	0.0017 (7)	−0.0025 (9)	0.0039 (6)
C8	0.0252 (10)	0.0222 (11)	0.0141 (9)	0.0027 (8)	−0.0011 (8)	0.0013 (9)
Fe1	0.01334 (15)	0.01485 (12)	0.01249 (12)	0.00061 (11)	−0.00019 (13)	−0.00033 (18)
Cl1	0.0209 (3)	0.0266 (3)	0.0129 (2)	0.0008 (2)	−0.0001 (2)	0.0009 (2)
Cl2	0.0195 (2)	0.0161 (2)	0.0235 (2)	0.00146 (19)	0.0012 (2)	−0.0027 (2)
Cl3	0.0161 (2)	0.0197 (3)	0.0177 (2)	0.00132 (19)	−0.00278 (18)	0.0002 (2)
Cl4	0.0182 (2)	0.0177 (2)	0.0186 (2)	−0.0018 (2)	0.0007 (2)	0.0004 (2)

Geometric parameters (Å, º)

N1—C5	1.515 (2)	C5—C6	1.517 (2)
N1—C7	1.523 (3)	C5—H5A	0.9900
N1—C3	1.525 (3)	C5—H5B	0.9900
N1—C1	1.527 (3)	C6—H6A	0.9800
C1—C2	1.507 (3)	C6—H6B	0.9800
C1—H1A	0.9900	C6—H6C	0.9800
C1—H1B	0.9900	C7—C8	1.520 (3)
C2—H2A	0.9800	C7—H7A	0.9900
C2—H2B	0.9800	C7—H7B	0.9900
C2—H2C	0.9800	C8—H8A	0.9800
C3—C4	1.514 (4)	C8—H8B	0.9800
C3—H3A	0.9900	C8—H8C	0.9800
C3—H3B	0.9900	Fe1—Cl4	2.1995 (6)
C4—H4A	0.9800	Fe1—Cl3	2.2007 (5)
C4—H4B	0.9800	Fe1—Cl1	2.2011 (6)
C4—H4C	0.9800	Fe1—Cl2	2.2068 (6)
C5—N1—C7	111.42 (15)	N1—C5—C6	115.30 (15)
C5—N1—C3	109.48 (15)	N1—C5—H5A	108.4
C7—N1—C3	108.28 (18)	C6—C5—H5A	108.4
C5—N1—C1	108.66 (16)	N1—C5—H5B	108.4
C7—N1—C1	108.18 (17)	C6—C5—H5B	108.4
C3—N1—C1	110.83 (16)	H5A—C5—H5B	107.5
C2—C1—N1	115.70 (17)	C5—C6—H6A	109.5
C2—C1—H1A	108.4	C5—C6—H6B	109.5
N1—C1—H1A	108.4	H6A—C6—H6B	109.5
C2—C1—H1B	108.4	C5—C6—H6C	109.5
N1—C1—H1B	108.4	H6A—C6—H6C	109.5
H1A—C1—H1B	107.4	H6B—C6—H6C	109.5
C1—C2—H2A	109.5	C8—C7—N1	115.35 (18)
C1—C2—H2B	109.5	C8—C7—H7A	108.4
H2A—C2—H2B	109.5	N1—C7—H7A	108.4
C1—C2—H2C	109.5	C8—C7—H7B	108.4
H2A—C2—H2C	109.5	N1—C7—H7B	108.4
H2B—C2—H2C	109.5	H7A—C7—H7B	107.5
C4—C3—N1	115.5 (2)	C7—C8—H8A	109.5
C4—C3—H3A	108.4	C7—C8—H8B	109.5
N1—C3—H3A	108.4	H8A—C8—H8B	109.5
C4—C3—H3B	108.4	C7—C8—H8C	109.5
N1—C3—H3B	108.4	H8A—C8—H8C	109.5
H3A—C3—H3B	107.5	H8B—C8—H8C	109.5
C3—C4—H4A	109.5	Cl4—Fe1—Cl3	108.70 (2)
C3—C4—H4B	109.5	Cl4—Fe1—Cl1	110.38 (3)
H4A—C4—H4B	109.5	Cl3—Fe1—Cl1	109.12 (3)
C3—C4—H4C	109.5	Cl4—Fe1—Cl2	110.71 (3)
H4A—C4—H4C	109.5	Cl3—Fe1—Cl2	110.12 (2)
H4B—C4—H4C	109.5	Cl1—Fe1—Cl2	107.79 (3)
C5—N1—C1—C2	176.67 (16)	C7—N1—C5—C6	51.1 (2)
C7—N1—C1—C2	55.6 (2)	C3—N1—C5—C6	170.84 (17)
C3—N1—C1—C2	−63.0 (2)	C1—N1—C5—C6	−68.0 (2)
C5—N1—C3—C4	57.5 (2)	C5—N1—C7—C8	54.5 (2)
C7—N1—C3—C4	179.18 (18)	C3—N1—C7—C8	−66.0 (2)
C1—N1—C3—C4	−62.3 (2)	C1—N1—C7—C8	173.87 (17)