Guanidinium chloro-chromate.

In the title compound, guanidinium chloridotrioxidochrom-ate(VI), (CH(6)N(3))[CrClO(3)], both the cation and anion are generated by crystallographic mirror symmetry, with one O and one N atom and the Cr, Cl and C atoms lying on the mirror plane. The bond lengths in the guanidinium cation are inter-mediate between normal C-N and C=N bond lengths, indicating significant delocalization in this species. In the crystal structure, inter-molecular N-H⋯Cl inter-actions generate R(2) (1)(6) ring motifs. These ring motifs are further inter-connected by inter-molecular N-H⋯O hydrogen bonds into infinite chains along [010].

Related literature

For background to chlorido­chromates in organic synthesis, see: Ghammaamy & Maza­reey (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶). For graph-set descriptions of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Al-Dajani et al. (2009 ▶); Lorenzo Luis et al. (1996 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

(CH6N3)[CrClO3]

M = 195.54

Orthorhombic,

a = 5.9708 (2) Å

b = 7.5302 (2) Å

c = 14.7085 (4) Å

V = 661.31 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.07 mm−1

T = 100 K

0.85 × 0.20 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.273, T max = 0.875

11570 measured reflections

1843 independent reflections

1727 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.020

wR(F 2) = 0.054

S = 1.10

1843 reflections

61 parameters

All H-atom parameters refined

Δρmax = 0.55 e Å−3

Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810002710/hb5314sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002710/hb5314Isup2.hkl

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

(CH6N3)[CrClO3]	F(000) = 392
Mr = 195.54	Dx = 1.964 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 7278 reflections
a = 5.9708 (2) Å	θ = 2.8–40.1°
b = 7.5302 (2) Å	µ = 2.07 mm−1
c = 14.7085 (4) Å	T = 100 K
V = 661.31 (3) Å3	Plate, yellow
Z = 4	0.85 × 0.20 × 0.07 mm

Bruker SMART APEXII CCD area-detector diffractometer	1843 independent reflections
Radiation source: fine-focus sealed tube	1727 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 37.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→10
Tmin = 0.273, Tmax = 0.875	k = −12→12
11570 measured reflections	l = −21→25

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) = 0.054	All H-atom parameters refined
S = 1.10	w = 1/[σ2(Fo2) + (0.0252P)2 + 0.1555P] where P = (Fo2 + 2Fc2)/3
1843 reflections	(Δ/σ)max < 0.001
61 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cr1	0.38355 (3)	0.2500	0.646530 (11)	0.00989 (5)
Cl1	0.57743 (4)	0.2500	0.518544 (17)	0.01422 (6)
O1	0.12221 (13)	0.2500	0.61735 (6)	0.01476 (14)
O2	0.44850 (10)	0.07267 (8)	0.70172 (4)	0.01594 (11)
N1	−0.15734 (17)	0.2500	0.31553 (7)	0.01472 (16)
N2	0.11145 (12)	0.09721 (9)	0.39621 (5)	0.01507 (12)
C1	0.02125 (18)	0.2500	0.36969 (7)	0.01107 (15)
H1N1	−0.218 (2)	0.1568 (19)	0.3047 (8)	0.024 (3)*
H1N2	0.060 (2)	0.0026 (19)	0.3789 (9)	0.024 (3)*
H2N2	0.221 (2)	0.0981 (19)	0.4289 (9)	0.027 (3)*

	U11	U22	U33	U12	U13	U23
Cr1	0.01033 (8)	0.00893 (7)	0.01042 (7)	0.000	−0.00080 (5)	0.000
Cl1	0.01339 (11)	0.01634 (11)	0.01294 (10)	0.000	0.00166 (8)	0.000
O1	0.0114 (3)	0.0166 (3)	0.0163 (3)	0.000	−0.0014 (3)	0.000
O2	0.0184 (3)	0.0132 (2)	0.0162 (2)	0.00135 (19)	−0.0015 (2)	0.00329 (18)
N1	0.0154 (4)	0.0121 (3)	0.0166 (4)	0.000	−0.0047 (3)	0.000
N2	0.0169 (3)	0.0099 (2)	0.0184 (3)	0.0013 (2)	−0.0047 (2)	0.0001 (2)
C1	0.0120 (4)	0.0106 (3)	0.0106 (4)	0.000	0.0014 (3)	0.000

Cr1—O2	1.6101 (6)	N1—H1N1	0.805 (14)
Cr1—O2i	1.6102 (6)	N2—C1	1.3289 (8)
Cr1—O1	1.6183 (8)	N2—H1N2	0.818 (14)
Cr1—Cl1	2.2099 (3)	N2—H2N2	0.811 (14)
N1—C1	1.3310 (14)	C1—N2i	1.3289 (8)
O2—Cr1—O2i	112.06 (4)	C1—N2—H1N2	120.7 (9)
O2—Cr1—O1	111.47 (3)	C1—N2—H2N2	119.5 (10)
O2i—Cr1—O1	111.47 (3)	H1N2—N2—H2N2	119.8 (14)
O2—Cr1—Cl1	107.66 (2)	N2i—C1—N2	119.94 (10)
O2i—Cr1—Cl1	107.66 (2)	N2i—C1—N1	120.02 (5)
O1—Cr1—Cl1	106.21 (3)	N2—C1—N1	120.02 (5)
C1—N1—H1N1	118.5 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2ii	0.806 (14)	2.211 (13)	2.9984 (9)	165.7 (12)
N2—H1N2···O1iii	0.817 (14)	2.192 (14)	2.9702 (8)	159.4 (13)
N2—H2N2···Cl1	0.812 (13)	2.753 (13)	3.5075 (8)	155.5 (13)

Table 1

Selected bond lengths (Å)

Cr1—O2	1.6101 (6)
Cr1—O2	1.6183 (8)
Cr1—Cl1	2.2099 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2ii	0.806 (14)	2.211 (13)	2.9984 (9)	165.7 (12)
N2—H1N2⋯O1iii	0.817 (14)	2.192 (14)	2.9702 (8)	159.4 (13)
N2—H2N2⋯Cl1	0.812 (13)	2.753 (13)	3.5075 (8)	155.5 (13)

Symmetry codes: (ii) ; (iii) .