Creatininium 2-chloro-acetate.

IN THE TITLE COMPOUND (SYSTEMATIC NAME: 2-amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-3-ium 2-chloro-acetate), C(4)H(8)N(3)O(+)·C(2)H(2)ClO(2) (-), the mol-ecular aggregations are stabil-ized through classical (N-H⋯O) and non-classical (C-H⋯O and C-H⋯N) hydrogen-bonding inter-actions. The cations are linked to the anions, forming ion pairs through two N-H⋯O bonds that produce characteristic R(2) (2)(8) ring motifs. These cation-anion pairs are connected through another N-H⋯O hydrogen bond, leading to an R(4) (2)(8) ring motif. Further weak C-H⋯N inter-actions link the mol-ecules along the a axis, while other C-H⋯O inter-actions generate zigzag chains extending along b.

Related literature

For related structures, see: Ali et al. (2011a ▶,b ▶); Bahadur, Kannan et al. (2007 ▶); Bahadur, Sivapragasam et al. (2007 ▶); Bahadur, Rajalakshmi et al. (2007 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the biological importance of creatinine, see: Madaras & Buck (1996 ▶); Sharma et al. (2004 ▶); Narayanan & Appleton (1980 ▶).

Experimental

Crystal data

C4H8N3O+·C2H2ClO2 −

M = 207.62

Monoclinic,

a = 5.7993 (8) Å

b = 13.934 (2) Å

c = 11.2205 (16) Å

β = 95.326 (2)°

V = 902.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.40 mm−1

T = 294 K

0.24 × 0.22 × 0.19 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

8205 measured reflections

1587 independent reflections

1472 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.117

S = 1.05

1587 reflections

131 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL/PC (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL/PC; molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812012068/sj5215sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012068/sj5215Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812012068/sj5215Isup3.cml

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

C4H8N3O+·C2H2ClO2−	F(000) = 432
Mr = 207.62	Dx = 1.527 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2516 reflections
a = 5.7993 (8) Å	θ = 2.2–23.4°
b = 13.934 (2) Å	µ = 0.40 mm−1
c = 11.2205 (16) Å	T = 294 K
β = 95.326 (2)°	Block, colourless
V = 902.8 (2) Å3	0.24 × 0.22 × 0.19 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	1472 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 25.0°, θmin = 2.3°
ω scans	h = −6→6
8205 measured reflections	k = −16→16
1587 independent 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0666P)2 + 0.3396P] where P = (Fo2 + 2Fc2)/3
1587 reflections	(Δ/σ)max < 0.001
131 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.27 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
N11	1.0950 (2)	0.16015 (11)	0.55491 (13)	0.0435 (4)
C11	1.1347 (4)	0.13325 (16)	0.67962 (17)	0.0517 (5)
H11A	1.0491	0.1753	0.7270	0.078*
H11B	1.2969	0.1383	0.7052	0.078*
H11C	1.0845	0.0683	0.6895	0.078*
C12	1.2339 (3)	0.22831 (14)	0.49571 (17)	0.0474 (5)
H12A	1.3926	0.2064	0.4957	0.057*
H12B	1.2328	0.2908	0.5336	0.057*
C13	1.1149 (3)	0.23140 (13)	0.37071 (18)	0.0471 (5)
O13	1.1682 (3)	0.27677 (12)	0.28629 (14)	0.0668 (5)
N14	0.9267 (3)	0.17187 (11)	0.37131 (14)	0.0434 (4)
C15	0.9179 (3)	0.13198 (12)	0.48112 (15)	0.0390 (4)
N15	0.7527 (3)	0.07372 (13)	0.50395 (16)	0.0482 (4)
H1N	0.741 (4)	0.0498 (17)	0.569 (2)	0.063 (7)*
H2N	0.636 (4)	0.0637 (17)	0.441 (2)	0.062 (6)*
H14N	0.835 (4)	0.1546 (17)	0.311 (2)	0.062 (7)*
C21	0.4400 (3)	0.07309 (13)	0.22026 (16)	0.0434 (4)
C22	0.2464 (4)	0.04780 (17)	0.12518 (18)	0.0561 (5)
H22A	0.0995	0.0614	0.1564	0.067*
H22B	0.2520	−0.0206	0.1099	0.067*
O21	0.6111 (2)	0.11830 (11)	0.19341 (13)	0.0578 (4)
O22	0.4072 (2)	0.04254 (11)	0.32210 (12)	0.0547 (4)
Cl1	0.25524 (10)	0.10901 (5)	−0.01176 (5)	0.0725 (3)

	U11	U22	U33	U12	U13	U23
N11	0.0406 (8)	0.0488 (8)	0.0392 (8)	−0.0010 (6)	−0.0055 (6)	−0.0015 (6)
C11	0.0518 (11)	0.0622 (12)	0.0390 (10)	0.0059 (9)	−0.0074 (8)	−0.0025 (9)
C12	0.0363 (9)	0.0517 (11)	0.0536 (11)	−0.0030 (7)	0.0016 (8)	−0.0055 (8)
C13	0.0405 (9)	0.0501 (10)	0.0510 (11)	−0.0005 (8)	0.0067 (8)	0.0015 (8)
O13	0.0589 (9)	0.0813 (11)	0.0612 (10)	−0.0129 (7)	0.0108 (7)	0.0176 (8)
N14	0.0409 (8)	0.0507 (9)	0.0373 (8)	−0.0039 (6)	−0.0028 (6)	0.0016 (6)
C15	0.0382 (9)	0.0401 (8)	0.0379 (9)	0.0037 (7)	−0.0009 (7)	−0.0010 (7)
N15	0.0462 (10)	0.0556 (10)	0.0414 (9)	−0.0097 (7)	−0.0043 (8)	0.0082 (7)
C21	0.0448 (10)	0.0456 (9)	0.0380 (9)	−0.0027 (7)	−0.0056 (8)	0.0014 (7)
C22	0.0539 (11)	0.0694 (13)	0.0427 (10)	−0.0161 (10)	−0.0087 (9)	0.0053 (9)
O21	0.0544 (8)	0.0748 (10)	0.0418 (8)	−0.0223 (7)	−0.0081 (6)	0.0098 (6)
O22	0.0545 (8)	0.0661 (9)	0.0413 (8)	−0.0140 (7)	−0.0068 (6)	0.0123 (6)
Cl1	0.0710 (4)	0.0998 (5)	0.0426 (3)	−0.0207 (3)	−0.0164 (3)	0.0133 (3)

N11—C15	1.318 (2)	N14—C15	1.357 (2)
N11—C12	1.446 (2)	N14—H14N	0.86 (3)
N11—C11	1.446 (2)	C15—N15	1.299 (2)
C11—H11A	0.9600	N15—H1N	0.81 (3)
C11—H11B	0.9600	N15—H2N	0.94 (3)
C11—H11C	0.9600	C21—O21	1.236 (2)
C12—C13	1.505 (3)	C21—O22	1.251 (2)
C12—H12A	0.9700	C21—C22	1.517 (2)
C12—H12B	0.9700	C22—Cl1	1.762 (2)
C13—O13	1.203 (2)	C22—H22A	0.9700
C13—N14	1.371 (2)	C22—H22B	0.9700
C15—N11—C12	109.98 (15)	C15—N14—C13	110.45 (16)
C15—N11—C11	125.12 (16)	C15—N14—H14N	122.0 (16)
C12—N11—C11	124.71 (15)	C13—N14—H14N	127.1 (16)
N11—C11—H11A	109.5	N15—C15—N11	127.46 (17)
N11—C11—H11B	109.5	N15—C15—N14	121.71 (16)
H11A—C11—H11B	109.5	N11—C15—N14	110.83 (16)
N11—C11—H11C	109.5	C15—N15—H1N	124.1 (18)
H11A—C11—H11C	109.5	C15—N15—H2N	116.0 (14)
H11B—C11—H11C	109.5	H1N—N15—H2N	120 (2)
N11—C12—C13	102.72 (14)	O21—C21—O22	126.16 (17)
N11—C12—H12A	111.2	O21—C21—C22	120.37 (16)
C13—C12—H12A	111.2	O22—C21—C22	113.46 (16)
N11—C12—H12B	111.2	C21—C22—Cl1	114.92 (14)
C13—C12—H12B	111.2	C21—C22—H22A	108.5
H12A—C12—H12B	109.1	Cl1—C22—H22A	108.5
O13—C13—N14	125.77 (19)	C21—C22—H22B	108.5
O13—C13—C12	128.30 (18)	Cl1—C22—H22B	108.5
N14—C13—C12	105.92 (16)	H22A—C22—H22B	107.5
C15—N11—C12—C13	−3.13 (19)	C11—N11—C15—N15	−2.4 (3)
C11—N11—C12—C13	−178.40 (16)	C12—N11—C15—N14	2.9 (2)
N11—C12—C13—O13	−178.5 (2)	C11—N11—C15—N14	178.17 (16)
N11—C12—C13—N14	2.23 (19)	C13—N14—C15—N15	179.15 (17)
O13—C13—N14—C15	−179.97 (19)	C13—N14—C15—N11	−1.4 (2)
C12—C13—N14—C15	−0.7 (2)	O21—C21—C22—Cl1	−13.4 (3)
C12—N11—C15—N15	−177.63 (18)	O22—C21—C22—Cl1	167.75 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N15—H1N···O22i	0.81 (3)	2.02 (3)	2.762 (2)	152 (2)
N15—H2N···O22	0.94 (3)	1.82 (3)	2.758 (2)	179 (2)
N14—H14N···O21	0.86 (3)	1.83 (3)	2.686 (2)	173 (2)
C11—H11A···O13ii	0.96	2.46	3.305 (3)	147
C11—H11B···O13iii	0.96	2.55	3.448 (3)	156
C12—H12A···N15iv	0.97	2.78	3.695 (3)	157
C12—H12B···O21iii	0.97	2.36	3.208 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N15—H1N⋯O22i	0.81 (3)	2.02 (3)	2.762 (2)	152 (2)
N15—H2N⋯O22	0.94 (3)	1.82 (3)	2.758 (2)	179 (2)
N14—H14N⋯O21	0.86 (3)	1.83 (3)	2.686 (2)	173 (2)
C11—H11A⋯O13ii	0.96	2.46	3.305 (3)	147
C11—H11B⋯O13iii	0.96	2.55	3.448 (3)	156
C12—H12A⋯N15iv	0.97	2.78	3.695 (3)	157
C12—H12B⋯O21iii	0.97	2.36	3.208 (2)	146

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