Creatinium perchlorate.

The title compound, C(4)H(8)N(3)O(+)·ClO(4) (-), is built up from creatininium cations and perchlorate anions. Crystal cohesion and perchlorate stability are ensured by N-H⋯O hydrogen bonds that together with weak C-H⋯O inter-actions build up a three-dimensional network.

Related literature

For background on organic–inorganic hybrid materials, see: Benali-Cherif et al. (2004 ▶); Hill (1998 ▶); Kagan et al. (1999 ▶). For a related structure, see: Cherouana et al. (2003 ▶); Berrah et al. (2005 ▶). For inter­pretation of the solution acidity effect on NMR chemical shifts, see: Kotsyubynskyy et al. (2004 ▶).

Experimental

Crystal data

C4H8N3O+·ClO4 −

M = 213.58

Monoclinic,

a = 5.8023 (3) Å

b = 20.7782 (13) Å

c = 7.3250 (4) Å

β = 107.947 (4)°

V = 840.14 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.45 mm−1

T = 293 (2) K

0.10 × 0.10 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

4080 measured reflections

1587 independent reflections

1209 reflections with I > 2σ(I)

R int = 0.126

Refinement

R[F 2 > 2σ(F 2)] = 0.075

wR(F 2) = 0.230

S = 1.05

1587 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.42 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003171/dn2425sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003171/dn2425Isup2.hkl

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

C4H8N3O+·ClO4−	F(000) = 440
Mr = 213.58	Dx = 1.689 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4863 reflections
a = 5.8023 (3) Å	θ = 2.0–26.0°
b = 20.7782 (13) Å	µ = 0.45 mm−1
c = 7.3250 (4) Å	T = 293 K
β = 107.947 (4)°	Prism, colourless
V = 840.14 (8) Å3	0.10 × 0.10 × 0.10 mm
Z = 4

Nonius KappaCCD diffractometer	1209 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.126
graphite	θmax = 26.0°, θmin = 2.0°
ω–θ scans	h = −7→6
4080 measured reflections	k = −23→25
1587 independent reflections	l = −9→9

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.230	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.139P)2 + 0.288P] where P = (Fo2 + 2Fc2)/3
1586 reflections	(Δ/σ)max = 0.003
119 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.41 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
O5	0.3264 (6)	0.74385 (13)	0.3068 (5)	0.0803 (9)
N1	0.4969 (5)	0.65462 (13)	0.4848 (5)	0.0623 (8)
H1	0.5899	0.6421	0.4202	0.075*
N2	0.5866 (6)	0.57013 (14)	0.7078 (6)	0.0723 (10)
H2A	0.5667	0.5522	0.8077	0.087*
H2B	0.6800	0.5526	0.6508	0.087*
N3	0.3285 (5)	0.65583 (13)	0.7149 (4)	0.0577 (8)
C2	0.4753 (6)	0.62392 (16)	0.6428 (5)	0.0555 (8)
C3	0.2475 (8)	0.6361 (2)	0.8757 (6)	0.0729 (11)
H3A	0.2690	0.5905	0.8942	0.109*
H3B	0.0793	0.6466	0.8491	0.109*
H3C	0.3409	0.6581	0.9897	0.109*
C4	0.2340 (7)	0.71236 (15)	0.5973 (6)	0.0622 (10)
H4A	0.2797	0.7516	0.6713	0.075*
H4B	0.0588	0.7106	0.5451	0.075*
C5	0.3498 (7)	0.70880 (15)	0.4411 (6)	0.0628 (10)
Cl1	0.89960 (16)	0.57125 (4)	0.24596 (14)	0.0599 (5)
O1	0.8635 (8)	0.63394 (16)	0.1663 (8)	0.1392 (18)
O2	0.7200 (7)	0.52990 (16)	0.1320 (6)	0.1017 (12)
O3	1.1298 (6)	0.5496 (2)	0.2543 (6)	0.1112 (13)
O4	0.8863 (10)	0.5762 (3)	0.4326 (7)	0.1394 (19)

	U11	U22	U33	U12	U13	U23
O5	0.105 (2)	0.0604 (16)	0.085 (2)	−0.0036 (14)	0.0420 (17)	0.0152 (14)
N1	0.0699 (17)	0.0527 (16)	0.075 (2)	−0.0020 (13)	0.0384 (16)	−0.0039 (14)
N2	0.082 (2)	0.0549 (19)	0.088 (2)	0.0147 (14)	0.0381 (19)	0.0059 (15)
N3	0.0663 (16)	0.0474 (15)	0.0692 (19)	0.0027 (13)	0.0353 (14)	0.0031 (13)
C2	0.0587 (18)	0.0449 (16)	0.066 (2)	−0.0009 (14)	0.0244 (16)	−0.0049 (15)
C3	0.087 (3)	0.064 (2)	0.079 (3)	0.008 (2)	0.042 (2)	0.0080 (19)
C4	0.074 (2)	0.0415 (17)	0.081 (3)	0.0048 (15)	0.0369 (19)	0.0024 (15)
C5	0.072 (2)	0.0421 (17)	0.081 (3)	−0.0083 (15)	0.0334 (19)	−0.0017 (16)
Cl1	0.0651 (7)	0.0471 (6)	0.0728 (7)	0.0028 (3)	0.0289 (5)	−0.0067 (3)
O1	0.144 (3)	0.0463 (18)	0.198 (5)	0.0036 (19)	0.010 (3)	0.017 (2)
O2	0.110 (2)	0.074 (2)	0.108 (3)	−0.0300 (17)	0.014 (2)	0.0009 (17)
O3	0.088 (2)	0.104 (3)	0.155 (4)	0.015 (2)	0.058 (2)	−0.016 (3)
O4	0.164 (4)	0.187 (5)	0.091 (3)	0.029 (3)	0.074 (3)	−0.019 (3)

O5—C5	1.197 (5)	C3—H3A	0.9600
N1—C2	1.361 (4)	C3—H3B	0.9600
N1—C5	1.389 (5)	C3—H3C	0.9600
N1—H1	0.8600	C4—C5	1.497 (6)
N2—C2	1.305 (4)	C4—H4A	0.9700
N2—H2A	0.8600	C4—H4B	0.9700
N2—H2B	0.8600	Cl1—O3	1.393 (3)
N3—C2	1.312 (4)	Cl1—O4	1.396 (4)
N3—C3	1.455 (5)	Cl1—O2	1.409 (3)
N3—C4	1.460 (4)	Cl1—O1	1.416 (4)
C2—N1—C5	111.4 (3)	H3B—C3—H3C	109.5
C2—N1—H1	124.3	N3—C4—C5	103.6 (3)
C5—N1—H1	124.3	N3—C4—H4A	111.0
C2—N2—H2A	120.0	C5—C4—H4A	111.0
C2—N2—H2B	120.0	N3—C4—H4B	111.0
H2A—N2—H2B	120.0	C5—C4—H4B	111.0
C2—N3—C3	126.5 (3)	H4A—C4—H4B	109.0
C2—N3—C4	110.0 (3)	O5—C5—N1	126.0 (4)
C3—N3—C4	123.3 (3)	O5—C5—C4	129.3 (3)
N2—C2—N3	126.6 (4)	N1—C5—C4	104.6 (3)
N2—C2—N1	123.1 (3)	O3—Cl1—O4	108.8 (3)
N3—C2—N1	110.3 (3)	O3—Cl1—O2	110.7 (3)
N3—C3—H3A	109.5	O4—Cl1—O2	111.8 (3)
N3—C3—H3B	109.5	O3—Cl1—O1	109.5 (3)
H3A—C3—H3B	109.5	O4—Cl1—O1	106.8 (3)
N3—C3—H3C	109.5	O2—Cl1—O1	109.2 (2)
H3A—C3—H3C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.86	2.18	2.905 (5)	142
N2—H2B···O4	0.86	2.33	3.044 (6)	141
N2—H2A···O2i	0.86	2.31	3.077 (6)	148
N2—H2A···O2ii	0.86	2.52	3.186 (5)	136
N2—H2B···O3iii	0.86	2.39	2.947 (5)	123
C3—H3A···O2ii	0.96	2.51	3.455 (5)	168
C4—H4A···O1iv	0.97	2.43	3.284 (5)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4	0.86	2.18	2.905 (5)	142
N2—H2B⋯O4	0.86	2.33	3.044 (6)	141
N2—H2A⋯O2i	0.86	2.31	3.077 (6)	148
N2—H2A⋯O2ii	0.86	2.52	3.186 (5)	136
N2—H2B⋯O3iii	0.86	2.39	2.947 (5)	123
C3—H3A⋯O2ii	0.96	2.51	3.455 (5)	168
C4—H4A⋯O1iv	0.97	2.43	3.284 (5)	147

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .