2-Carbamylpyridinium tetra-chlorido-ferrate(III).

The title compound, (C(6)H(7)N(2)O)[FeCl(4)], contains two carbamylpyridinium (picolinamidinium) cations, which are linked into chains by N(+)-H⋯O hydrogen bonds formed between protonated pyridyl N atoms and carbonyl groups. Tetra-chloridoferrate(III) anions lie between these chains, accepting N-H⋯Cl hydrogen bonds from both H atoms of the picolinamidium -NH(2) group.

Related literature

For related structures containing picolinamidium cations, see: Uçar et al. (2004 ▶); Gotoh et al. (2009 ▶).

Experimental

Crystal data

(C6H7N2O)[FeCl4]

M = 320.79

Monoclinic,

a = 13.5252 (8) Å

b = 6.1704 (3) Å

c = 14.1165 (7) Å

β = 93.853 (2)°

V = 1175.44 (11) Å3

Z = 4

Mo Kα radiation

μ = 2.16 mm−1

T = 180 K

0.40 × 0.30 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.484, T max = 0.672

15093 measured reflections

2808 independent reflections

2420 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.020

wR(F 2) = 0.049

S = 1.05

2808 reflections

140 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809040148/zq2012sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040148/zq2012Isup2.hkl

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

(C6H7N2O)[FeCl4]	F(000) = 636
Mr = 320.79	Dx = 1.813 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8949 reflections
a = 13.5252 (8) Å	θ = 2.2–28.1°
b = 6.1704 (3) Å	µ = 2.16 mm−1
c = 14.1165 (7) Å	T = 180 K
β = 93.853 (2)°	Block, yellow
V = 1175.44 (11) Å3	0.40 × 0.30 × 0.20 mm
Z = 4

Bruker–Nonius X8 APEXII CCD diffractometer	2808 independent reflections
Radiation source: fine-focus sealed tube	2420 reflections with I > 2σ(I)
graphite	Rint = 0.024
Thin–slice ω and φ scans	θmax = 28.3°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −17→15
Tmin = 0.484, Tmax = 0.672	k = −7→8
15093 measured reflections	l = −16→18

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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0236P)2 + 0.2718P] where P = (Fo2 + 2Fc2)/3
2808 reflections	(Δ/σ)max = 0.002
140 parameters	Δρmax = 0.26 e Å−3
2 restraints	Δρmin = −0.23 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
O1	0.68522 (7)	1.05039 (17)	0.72326 (8)	0.0328 (2)
N1	0.62577 (9)	0.68301 (19)	0.79936 (8)	0.0223 (2)
H1	0.6851 (13)	0.703 (3)	0.7851 (11)	0.029 (4)*
N2	0.53208 (10)	1.1233 (2)	0.65734 (10)	0.0332 (3)
H21	0.5522 (13)	1.219 (3)	0.6233 (12)	0.044 (5)*
H22	0.4739 (11)	1.081 (3)	0.6457 (13)	0.045 (5)*
C1	0.59653 (10)	1.0119 (2)	0.71214 (10)	0.0236 (3)
C2	0.55609 (10)	0.8255 (2)	0.76671 (9)	0.0201 (3)
C3	0.45980 (10)	0.7950 (2)	0.78930 (9)	0.0229 (3)
H3A	0.4095	0.8939	0.7674	0.027*
C4	0.43698 (10)	0.6185 (2)	0.84436 (10)	0.0251 (3)
H4A	0.3707	0.5966	0.8608	0.030*
C5	0.51019 (11)	0.4743 (2)	0.87552 (10)	0.0279 (3)
H5A	0.4948	0.3523	0.9128	0.034*
C6	0.60612 (11)	0.5101 (2)	0.85165 (10)	0.0266 (3)
H6A	0.6576	0.4128	0.8722	0.032*
Fe1	0.283137 (14)	0.53471 (3)	0.540664 (13)	0.02141 (7)
Cl1	0.38209 (3)	0.39866 (6)	0.43917 (3)	0.04193 (11)
Cl2	0.30476 (3)	0.37620 (6)	0.67908 (2)	0.02817 (9)
Cl3	0.31100 (3)	0.88308 (6)	0.55199 (3)	0.03815 (10)
Cl4	0.12782 (3)	0.49004 (7)	0.48904 (3)	0.03714 (10)

	U11	U22	U33	U12	U13	U23
O1	0.0187 (5)	0.0355 (6)	0.0441 (6)	−0.0075 (4)	0.0024 (5)	0.0018 (5)
N1	0.0161 (6)	0.0268 (6)	0.0242 (6)	−0.0002 (5)	0.0030 (5)	−0.0048 (5)
N2	0.0235 (7)	0.0325 (7)	0.0440 (8)	−0.0003 (6)	0.0041 (6)	0.0106 (6)
C1	0.0208 (7)	0.0231 (7)	0.0276 (7)	−0.0014 (5)	0.0058 (6)	−0.0055 (6)
C2	0.0186 (6)	0.0224 (6)	0.0194 (6)	−0.0013 (5)	0.0007 (5)	−0.0066 (5)
C3	0.0181 (7)	0.0290 (7)	0.0212 (7)	−0.0001 (5)	−0.0002 (5)	−0.0062 (6)
C4	0.0195 (7)	0.0341 (8)	0.0221 (7)	−0.0061 (6)	0.0048 (6)	−0.0083 (6)
C5	0.0337 (8)	0.0273 (7)	0.0232 (7)	−0.0047 (6)	0.0050 (6)	−0.0023 (6)
C6	0.0286 (8)	0.0259 (7)	0.0250 (7)	0.0032 (6)	−0.0001 (6)	−0.0015 (6)
Fe1	0.02269 (12)	0.01900 (10)	0.02251 (11)	−0.00276 (7)	0.00133 (8)	−0.00228 (8)
Cl1	0.0585 (3)	0.03076 (19)	0.0393 (2)	0.00053 (18)	0.0235 (2)	−0.00672 (16)
Cl2	0.03014 (19)	0.03054 (18)	0.02317 (18)	−0.00099 (14)	−0.00311 (14)	−0.00080 (14)
Cl3	0.0468 (2)	0.01959 (17)	0.0481 (2)	−0.00492 (15)	0.00358 (19)	−0.00486 (16)
Cl4	0.0283 (2)	0.0439 (2)	0.0376 (2)	−0.00929 (16)	−0.00973 (16)	0.01353 (17)

O1—C1	1.2225 (17)	C3—H3A	0.950
N1—C6	1.3341 (19)	C4—C5	1.381 (2)
N1—C2	1.3473 (18)	C4—H4A	0.950
N1—H1	0.85 (2)	C5—C6	1.380 (2)
N2—C1	1.319 (2)	C5—H5A	0.950
N2—H21	0.82 (1)	C6—H6A	0.950
N2—H22	0.84 (1)	Fe1—Cl3	2.1863 (4)
C1—C2	1.5073 (19)	Fe1—Cl2	2.1870 (4)
C2—C3	1.3744 (18)	Fe1—Cl1	2.1923 (4)
C3—C4	1.385 (2)	Fe1—Cl4	2.1941 (4)
C6—N1—C2	123.39 (13)	C5—C4—C3	120.23 (13)
C6—N1—H1	118.4 (11)	C5—C4—H4A	119.9
C2—N1—H1	118.2 (11)	C3—C4—H4A	119.9
C1—N2—H21	119.2 (13)	C6—C5—C4	119.00 (13)
C1—N2—H22	121.9 (13)	C6—C5—H5A	120.5
H21—N2—H22	117.1 (19)	C4—C5—H5A	120.5
O1—C1—N2	125.32 (14)	N1—C6—C5	119.25 (14)
O1—C1—C2	117.99 (13)	N1—C6—H6A	120.4
N2—C1—C2	116.68 (12)	C5—C6—H6A	120.4
N1—C2—C3	118.90 (13)	Cl3—Fe1—Cl2	111.243 (17)
N1—C2—C1	113.78 (12)	Cl3—Fe1—Cl1	108.329 (17)
C3—C2—C1	127.24 (12)	Cl2—Fe1—Cl1	111.207 (17)
C2—C3—C4	119.22 (13)	Cl3—Fe1—Cl4	107.713 (18)
C2—C3—H3A	120.4	Cl2—Fe1—Cl4	107.946 (16)
C4—C3—H3A	120.4	Cl1—Fe1—Cl4	110.350 (19)
C6—N1—C2—C3	1.15 (19)	N1—C2—C3—C4	−0.38 (19)
C6—N1—C2—C1	178.00 (12)	C1—C2—C3—C4	−176.75 (13)
O1—C1—C2—N1	−19.00 (18)	C2—C3—C4—C5	−0.5 (2)
N2—C1—C2—N1	162.32 (12)	C3—C4—C5—C6	0.6 (2)
O1—C1—C2—C3	157.53 (14)	C2—N1—C6—C5	−1.0 (2)
N2—C1—C2—C3	−21.1 (2)	C4—C5—C6—N1	0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.85 (2)	2.00 (2)	2.7234 (16)	142 (2)
N2—H22···Cl3	0.84 (1)	2.78 (2)	3.5710 (15)	160 (2)
N2—H21···Cl1ii	0.82 (1)	2.69 (2)	3.4811 (14)	163 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.85 (2)	2.00 (2)	2.7234 (16)	142 (2)
N2—H22⋯Cl3	0.84 (1)	2.78 (2)	3.5710 (15)	160 (2)
N2—H21⋯Cl1ii	0.82 (1)	2.69 (2)	3.4811 (14)	163 (2)

Symmetry codes: (i) ; (ii) .