4-(Dimethyl-amino)-pyridinium tetra-chloridoferrate(III).

The title salt, (C7H11N2)[FeCl4], consists of one essentially planar (the r.m.s. deviation for all non-H atoms being 0.004 Å) 4-(dimethyl-amino)-pyridinium cation and a tetra-hedral tetra-chloridoferrate(III) anion. The cations and anions are arranged in layers parallel to (010). Besides electrostatic inter-actions, the crystal packing features N-H⋯Cl and C-H⋯Cl hydrogen bonds between cations and anions, forming a three-dimensional network.

Related literature

For background to hybrid compounds based on protonated substituted N-heterocyclic ligands, see: Bouacida (2008 ▶); Bouacida et al. (2007 ▶, 2009 ▶). For a related structure, see: Nenwa et al. (2010 ▶).

Experimental

Crystal data

(C7H11N2)[FeCl4]

M = 320.83

Monoclinic,

a = 9.0360 (2) Å

b = 14.0492 (5) Å

c = 10.2077 (3) Å

β = 98.7259 (9)°

V = 1280.85 (7) Å3

Z = 4

Mo Kα radiation

μ = 1.98 mm−1

T = 100 K

0.17 × 0.12 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2011 ▶) T min = 0.789, T max = 0.924

11192 measured reflections

2925 independent reflections

2146 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.081

S = 1.03

2925 reflections

133 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.94 e Å−3

Δρmin = −0.56 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2011 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681300603X/wm2729sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681300603X/wm2729Isup2.hkl

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

(C7H11N2)[FeCl4]	F(000) = 644
Mr = 320.83	Dx = 1.664 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2278 reflections
a = 9.0360 (2) Å	θ = 2.9–26.5°
b = 14.0492 (5) Å	µ = 1.98 mm−1
c = 10.2077 (3) Å	T = 100 K
β = 98.7259 (9)°	Plate, orange
V = 1280.85 (7) Å3	0.17 × 0.12 × 0.04 mm
Z = 4

Bruker APEXII CCD diffractometer	2925 independent reflections
Radiation source: sealed tube	2146 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
φ and ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2011)	h = −8→11
Tmin = 0.789, Tmax = 0.924	k = −18→18
11192 measured reflections	l = −13→13

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0258P)2 + 0.6542P] where P = (Fo2 + 2Fc2)/3
2925 reflections	(Δ/σ)max = 0.001
133 parameters	Δρmax = 0.94 e Å−3
0 restraints	Δρmin = −0.56 e Å−3

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
Fe1	−0.02427 (4)	0.25669 (2)	0.72252 (3)	0.02371 (11)
Cl1	−0.16650 (8)	0.13001 (5)	0.71136 (7)	0.0449 (2)
Cl2	0.11905 (7)	0.25489 (4)	0.91821 (6)	0.03315 (17)
Cl3	0.11063 (8)	0.25245 (5)	0.56193 (7)	0.03676 (18)
Cl4	−0.15646 (8)	0.38804 (5)	0.70930 (7)	0.03842 (18)
C1	0.3730 (3)	0.42873 (17)	0.8197 (3)	0.0281 (6)
H1	0.381	0.4214	0.913	0.034*
C2	0.4618 (3)	0.37690 (19)	0.7516 (3)	0.0374 (7)
H2	0.5322	0.3338	0.7976	0.045*
N3	0.4513 (3)	0.38586 (19)	0.6189 (3)	0.0445 (7)
H3	0.506 (4)	0.355 (2)	0.582 (3)	0.059 (11)*
C4	0.3518 (3)	0.4461 (2)	0.5506 (3)	0.0417 (7)
H4	0.3453	0.4501	0.457	0.05*
C5	0.2614 (3)	0.50068 (19)	0.6130 (3)	0.0331 (6)
H5	0.1935	0.5436	0.5635	0.04*
C6	0.2677 (3)	0.49407 (17)	0.7526 (2)	0.0260 (6)
N7	0.1790 (2)	0.54643 (15)	0.8167 (2)	0.0305 (5)
C8	0.1866 (3)	0.5381 (2)	0.9603 (3)	0.0407 (7)
H8A	0.1606	0.4731	0.9829	0.061*
H8B	0.116	0.5829	0.9908	0.061*
H8C	0.2884	0.5529	1.0036	0.061*
C9	0.0706 (3)	0.6131 (2)	0.7463 (3)	0.0448 (8)
H9A	0.1236	0.6617	0.7024	0.067*
H9B	0.0143	0.6437	0.8095	0.067*
H9C	0.0013	0.5786	0.6797	0.067*

	U11	U22	U33	U12	U13	U23
Fe1	0.0239 (2)	0.0260 (2)	0.02024 (19)	−0.00208 (14)	0.00016 (14)	0.00140 (15)
Cl1	0.0505 (4)	0.0485 (4)	0.0315 (4)	−0.0268 (3)	−0.0077 (3)	0.0074 (3)
Cl2	0.0327 (3)	0.0370 (4)	0.0261 (3)	−0.0089 (3)	−0.0072 (3)	0.0047 (3)
Cl3	0.0380 (4)	0.0417 (4)	0.0330 (4)	−0.0003 (3)	0.0131 (3)	−0.0032 (3)
Cl4	0.0419 (4)	0.0406 (4)	0.0322 (4)	0.0157 (3)	0.0035 (3)	0.0016 (3)
C1	0.0269 (13)	0.0283 (14)	0.0287 (14)	−0.0048 (11)	0.0035 (11)	0.0028 (11)
C2	0.0331 (15)	0.0305 (15)	0.050 (2)	−0.0057 (12)	0.0092 (13)	0.0032 (13)
N3	0.0481 (16)	0.0367 (15)	0.0554 (18)	−0.0106 (12)	0.0295 (14)	−0.0140 (13)
C4	0.0578 (19)	0.0419 (17)	0.0266 (16)	−0.0218 (15)	0.0103 (14)	−0.0071 (13)
C5	0.0404 (16)	0.0321 (15)	0.0255 (14)	−0.0088 (12)	0.0002 (12)	−0.0008 (11)
C6	0.0276 (14)	0.0264 (13)	0.0235 (13)	−0.0107 (11)	0.0022 (11)	−0.0001 (10)
N7	0.0314 (12)	0.0300 (12)	0.0299 (13)	−0.0015 (9)	0.0036 (10)	−0.0003 (10)
C8	0.0467 (17)	0.0427 (17)	0.0360 (17)	−0.0037 (14)	0.0167 (14)	−0.0030 (13)
C9	0.0347 (16)	0.0370 (17)	0.061 (2)	0.0049 (13)	0.0025 (14)	0.0062 (15)

Fe1—Cl3	2.1870 (7)	C4—H4	0.95
Fe1—Cl1	2.1882 (7)	C5—C6	1.420 (3)
Fe1—Cl4	2.1912 (7)	C5—H5	0.95
Fe1—Cl2	2.2097 (7)	C6—N7	1.331 (3)
C1—C2	1.351 (4)	N7—C8	1.462 (3)
C1—C6	1.421 (3)	N7—C9	1.463 (3)
C1—H1	0.95	C8—H8A	0.98
C2—N3	1.350 (4)	C8—H8B	0.98
C2—H2	0.95	C8—H8C	0.98
N3—C4	1.349 (4)	C9—H9A	0.98
N3—H3	0.79 (3)	C9—H9B	0.98
C4—C5	1.348 (4)	C9—H9C	0.98
Cl3—Fe1—Cl1	109.18 (3)	C6—C5—H5	119.9
Cl3—Fe1—Cl4	109.72 (3)	N7—C6—C5	121.4 (2)
Cl1—Fe1—Cl4	111.80 (3)	N7—C6—C1	122.0 (2)
Cl3—Fe1—Cl2	111.12 (3)	C5—C6—C1	116.6 (2)
Cl1—Fe1—Cl2	107.27 (3)	C6—N7—C8	120.6 (2)
Cl4—Fe1—Cl2	107.73 (3)	C6—N7—C9	121.4 (2)
C2—C1—C6	120.4 (3)	C8—N7—C9	118.0 (2)
C2—C1—H1	119.8	N7—C8—H8A	109.5
C6—C1—H1	119.8	N7—C8—H8B	109.5
N3—C2—C1	120.6 (3)	H8A—C8—H8B	109.5
N3—C2—H2	119.7	N7—C8—H8C	109.5
C1—C2—H2	119.7	H8A—C8—H8C	109.5
C4—N3—C2	121.1 (3)	H8B—C8—H8C	109.5
C4—N3—H3	121 (3)	N7—C9—H9A	109.5
C2—N3—H3	118 (3)	N7—C9—H9B	109.5
C5—C4—N3	121.1 (3)	H9A—C9—H9B	109.5
C5—C4—H4	119.4	N7—C9—H9C	109.5
N3—C4—H4	119.4	H9A—C9—H9C	109.5
C4—C5—C6	120.1 (3)	H9B—C9—H9C	109.5
C4—C5—H5	119.9
C6—C1—C2—N3	−0.4 (4)	C2—C1—C6—N7	−179.8 (2)
C1—C2—N3—C4	−0.4 (4)	C2—C1—C6—C5	0.4 (3)
C2—N3—C4—C5	1.3 (4)	C5—C6—N7—C8	179.6 (2)
N3—C4—C5—C6	−1.3 (4)	C1—C6—N7—C8	−0.2 (4)
C4—C5—C6—N7	−179.4 (2)	C5—C6—N7—C9	0.1 (4)
C4—C5—C6—C1	0.4 (3)	C1—C6—N7—C9	−179.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···Cl2i	0.79 (3)	2.60 (3)	3.369 (3)	165 (3)
C4—H4···Cl1i	0.95	2.74	3.604 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯Cl2i	0.79 (3)	2.60 (3)	3.369 (3)	165 (3)
C4—H4⋯Cl1i	0.95	2.74	3.604 (3)	152

Symmetry code: (i) .