Bis(creatininium) tetra-chlorido-cadmate(II).

In the title compound, (C(4)H(8)N(3)O)(2)[CdCl(4)], the asymmetric unit comprises two creatininium cations and one tetra-chloridocadmate anion. Cd⋯O secondary bonding links one of the two imidazole rings and the anion into ion pairs. The free and bound cations form layers between which the [CdCl(4)](2-) anions are sandwiched. The Cd(II) atom adopts a distorted trigonal-bipyramidal geometry in which the Cd⋯O bond is axial. Inter-molecular N-H⋯Cl hydrogen bonds form a two-dimensional network parallel to (001) which ensures the junction between creatininium cations and [CdCl(4)](2-) anions.

Related literature

An abnormal level of creatinine in biological fluids is an indicator of various medical conditions, see: Narayanan & Appleton (1980 ▶). For inter­actions between creatinine and biologically important metal ions, see: Canty et al. (1979 ▶). Different complex species are formed depending on the reaction conditions, see: Nishida & Kida (1985 ▶). For bond lengths in the neutral creatinine mol­ecule, see: Smith & White (2001 ▶) and in creatinium compounds, see: Wilkinson & Harrison (2005 ▶). For Cd—Cl bond distances in dichlorido­bis(creatinine)cadmium(II), see: Okabe et al. (1995 ▶). For Cl—Cd—Cl bond angles in bis­(2,3,5-triphenyl­tetra­zolium)tetra­chloridocadmate(II), see: Zhang et al. (2007 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶); Etter et al. (1990 ▶).

Experimental

Crystal data

(C4H8N3O)2[CdCl4]

M = 482.48

Triclinic,

a = 7.5203 (4) Å

b = 7.6761 (3) Å

c = 15.0757 (7) Å

α = 79.476 (2)°

β = 85.438 (5)°

γ = 83.214 (3)°

V = 848.14 (7) Å3

Z = 2

Mo Kα radiation

μ = 1.93 mm−1

T = 100 K

0.25 × 0.15 × 0.1 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick,1996 ▶) T min = 0.644, T max = 0.831

10950 measured reflections

3843 independent reflections

3711 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.019

wR(F 2) = 0.048

S = 1.11

3843 reflections

216 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.77 e Å−3

Δρmin = −0.54 e Å−3

Data collection: COLLECT (Nonius, 2002 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026944/bt2978sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026944/bt2978Isup2.hkl

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

(C4H8N3O)2[CdCl4]	Z = 2
Mr = 482.48	F(000) = 476
Triclinic, P1	Dx = 1.889 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5203 (4) Å	Cell parameters from 8132 reflections
b = 7.6761 (3) Å	θ = 2.7–27.4°
c = 15.0757 (7) Å	µ = 1.93 mm−1
α = 79.476 (2)°	T = 100 K
β = 85.438 (5)°	Plates, colourless
γ = 83.214 (3)°	0.25 × 0.15 × 0.1 mm
V = 848.14 (7) Å3

Nonius KappaCCD diffractometer	3843 independent reflections
Radiation source: fine-focus sealed X-ray tube	3711 reflections with I > 2σ(I)
graphite	Rint = 0.064
φ scans, and ω scans with κ offsets	θmax = 27.4°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick,1996)	h = −9→9
Tmin = 0.644, Tmax = 0.831	k = −9→9
10950 measured reflections	l = −19→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.019	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.048	w = 1/[σ2(Fo2) + (0.0154P)2 + 0.4426P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.002
3843 reflections	Δρmax = 0.77 e Å−3
216 parameters	Δρmin = −0.54 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.08 (2)

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.

	x	y	z	Uiso*/Ueq
Cd1	0.066723 (15)	0.225860 (16)	0.280951 (8)	0.01066 (5)
Cl1	−0.04670 (6)	0.54257 (6)	0.24433 (3)	0.01616 (9)
Cl2	0.36325 (5)	0.13754 (7)	0.34349 (3)	0.01814 (10)
Cl3	0.14704 (6)	0.17937 (6)	0.11755 (3)	0.01524 (9)
Cl4	−0.15980 (5)	0.01360 (6)	0.32005 (3)	0.01418 (9)
O1	−0.01715 (17)	0.28215 (19)	0.45064 (9)	0.0176 (3)
N4	−0.3242 (2)	0.2622 (2)	0.47014 (11)	0.0130 (3)
N5	−0.38183 (19)	0.3218 (2)	0.60861 (10)	0.0134 (3)
N6	−0.6224 (2)	0.2535 (2)	0.53371 (12)	0.0179 (3)
C5	−0.1579 (2)	0.2895 (2)	0.49571 (12)	0.0127 (3)
C6	−0.4526 (2)	0.2762 (2)	0.53994 (12)	0.0126 (3)
C7	−0.1888 (2)	0.3305 (3)	0.59036 (12)	0.0144 (4)
H7A	−0.1208	0.2427	0.633	0.017*
H7B	−0.1565	0.4481	0.5929	0.017*
C8	−0.4703 (3)	0.3343 (3)	0.69777 (13)	0.0213 (4)
H8A	−0.4273	0.4292	0.7208	0.026*
H8B	−0.444	0.2239	0.7383	0.026*
H8C	−0.5976	0.358	0.6926	0.026*
O2	0.40943 (18)	0.36919 (18)	−0.10195 (9)	0.0191 (3)
N1	0.2474 (2)	0.5415 (2)	−0.00578 (11)	0.0139 (3)
C1	0.3552 (2)	0.5126 (2)	−0.08243 (12)	0.0138 (3)
C2	0.3922 (2)	0.6952 (2)	−0.13185 (12)	0.0127 (3)
H2A	0.52	0.7038	−0.1423	0.015*
H2B	0.3364	0.7239	−0.1893	0.015*
N2	0.1430 (2)	0.7800 (2)	0.07081 (11)	0.0176 (3)
N3	0.3113 (2)	0.8115 (2)	−0.06971 (10)	0.0129 (3)
C3	0.2295 (2)	0.7185 (2)	0.00098 (12)	0.0130 (3)
C4	0.3227 (3)	1.0033 (2)	−0.08903 (13)	0.0166 (4)
H4A	0.2574	1.0553	−0.1413	0.02*
H4B	0.4461	1.0256	−0.1004	0.02*
H4C	0.2722	1.0551	−0.0381	0.02*
H4	−0.340 (3)	0.224 (3)	0.4298 (17)	0.017 (6)*
H66	−0.689 (4)	0.238 (3)	0.5785 (19)	0.032 (7)*
H6	−0.653 (4)	0.215 (4)	0.486 (2)	0.038 (8)*
H1	0.212 (3)	0.462 (3)	0.0292 (17)	0.024 (6)*
H22	0.092 (3)	0.704 (3)	0.1156 (17)	0.024 (6)*
H2	0.142 (3)	0.884 (4)	0.0753 (18)	0.030 (7)*

	U11	U22	U33	U12	U13	U23
Cd1	0.00992 (7)	0.01213 (8)	0.01001 (7)	−0.00125 (5)	−0.00016 (5)	−0.00229 (5)
Cl1	0.0200 (2)	0.0126 (2)	0.0151 (2)	0.00070 (16)	−0.00008 (16)	−0.00248 (16)
Cl2	0.01099 (18)	0.0271 (3)	0.0158 (2)	0.00115 (16)	−0.00235 (15)	−0.00372 (18)
Cl3	0.0220 (2)	0.0142 (2)	0.0106 (2)	−0.00484 (16)	0.00282 (16)	−0.00459 (16)
Cl4	0.01278 (18)	0.0140 (2)	0.0155 (2)	−0.00334 (15)	0.00140 (15)	−0.00161 (16)
O1	0.0146 (6)	0.0226 (7)	0.0159 (7)	−0.0034 (5)	0.0043 (5)	−0.0055 (5)
N4	0.0150 (7)	0.0162 (8)	0.0090 (8)	−0.0040 (6)	0.0002 (6)	−0.0044 (6)
N5	0.0122 (7)	0.0171 (8)	0.0110 (7)	−0.0009 (6)	0.0017 (5)	−0.0042 (6)
N6	0.0132 (7)	0.0249 (9)	0.0151 (8)	−0.0055 (6)	−0.0003 (6)	−0.0005 (7)
C5	0.0147 (8)	0.0111 (9)	0.0121 (9)	−0.0020 (6)	0.0001 (6)	−0.0013 (7)
C6	0.0144 (8)	0.0101 (8)	0.0120 (8)	−0.0014 (6)	0.0008 (6)	0.0009 (7)
C7	0.0130 (8)	0.0181 (9)	0.0129 (9)	−0.0014 (6)	0.0001 (6)	−0.0052 (7)
C8	0.0223 (9)	0.0278 (11)	0.0132 (9)	−0.0003 (8)	0.0066 (7)	−0.0072 (8)
O2	0.0242 (7)	0.0130 (7)	0.0206 (7)	0.0005 (5)	−0.0015 (5)	−0.0059 (5)
N1	0.0178 (7)	0.0111 (8)	0.0125 (8)	−0.0033 (6)	0.0006 (6)	−0.0009 (6)
C1	0.0137 (8)	0.0155 (9)	0.0130 (9)	−0.0013 (6)	−0.0040 (7)	−0.0032 (7)
C2	0.0148 (8)	0.0135 (9)	0.0102 (8)	−0.0009 (6)	0.0008 (6)	−0.0039 (7)
N2	0.0241 (8)	0.0143 (9)	0.0143 (8)	−0.0038 (6)	0.0052 (6)	−0.0039 (7)
N3	0.0170 (7)	0.0105 (8)	0.0116 (7)	−0.0018 (6)	0.0014 (6)	−0.0034 (6)
C3	0.0140 (8)	0.0125 (9)	0.0129 (9)	−0.0022 (6)	−0.0019 (6)	−0.0021 (7)
C4	0.0226 (9)	0.0115 (9)	0.0158 (9)	−0.0026 (7)	0.0017 (7)	−0.0031 (7)

Cd1—Cl1	2.4571 (5)	C8—H8B	0.96
Cd1—Cl4	2.4596 (4)	C8—H8C	0.96
Cd1—Cl2	2.4627 (4)	O2—C1	1.208 (2)
Cd1—Cl3	2.5678 (4)	N1—C3	1.371 (2)
Cd1—O1	2.6854 (13)	N1—C1	1.394 (2)
O1—C5	1.213 (2)	N1—H1	0.79 (3)
N4—C6	1.380 (2)	C1—C2	1.508 (3)
N4—C5	1.387 (2)	C2—N3	1.460 (2)
N4—H4	0.75 (2)	C2—H2A	0.97
N5—C6	1.319 (2)	C2—H2B	0.97
N5—C7	1.463 (2)	N2—C3	1.325 (2)
N5—C8	1.466 (2)	N2—H22	0.90 (3)
N6—C6	1.322 (2)	N2—H2	0.81 (3)
N6—H66	0.81 (3)	N3—C3	1.321 (2)
N6—H6	0.87 (3)	N3—C4	1.459 (2)
C5—C7	1.511 (2)	C4—H4A	0.96
C7—H7A	0.97	C4—H4B	0.96
C7—H7B	0.97	C4—H4C	0.96
C8—H8A	0.96
Cl1—Cd1—Cl4	116.512 (15)	N5—C8—H8B	109.5
Cl1—Cd1—Cl2	120.122 (17)	H8A—C8—H8B	109.5
Cl4—Cd1—Cl2	117.621 (16)	N5—C8—H8C	109.5
Cl1—Cd1—Cl3	96.649 (15)	H8A—C8—H8C	109.5
Cl4—Cd1—Cl3	98.074 (15)	H8B—C8—H8C	109.5
Cl2—Cd1—Cl3	99.319 (15)	C3—N1—C1	110.39 (15)
Cl1—Cd1—O1	82.18 (3)	C3—N1—H1	127.6 (18)
Cl4—Cd1—O1	82.85 (3)	C1—N1—H1	121.8 (18)
Cl2—Cd1—O1	80.95 (3)	O2—C1—N1	125.86 (18)
Cl3—Cd1—O1	178.75 (3)	O2—C1—C2	128.57 (17)
C5—O1—Cd1	132.55 (13)	N1—C1—C2	105.55 (15)
C6—N4—C5	110.28 (15)	N3—C2—C1	102.80 (14)
C6—N4—H4	122.8 (18)	N3—C2—H2A	111.2
C5—N4—H4	125.3 (18)	C1—C2—H2A	111.2
C6—N5—C7	110.56 (14)	N3—C2—H2B	111.2
C6—N5—C8	126.70 (15)	C1—C2—H2B	111.2
C7—N5—C8	122.02 (15)	H2A—C2—H2B	109.1
C6—N6—H66	120.4 (19)	C3—N2—H22	119.4 (15)
C6—N6—H6	119.0 (19)	C3—N2—H2	120.6 (19)
H66—N6—H6	117 (3)	H22—N2—H2	120 (2)
O1—C5—N4	126.58 (18)	C3—N3—C4	127.85 (15)
O1—C5—C7	127.43 (17)	C3—N3—C2	110.50 (15)
N4—C5—C7	105.99 (14)	C4—N3—C2	121.64 (15)
N5—C6—N6	126.98 (17)	N3—C3—N2	127.02 (17)
N5—C6—N4	110.34 (15)	N3—C3—N1	110.42 (15)
N6—C6—N4	122.61 (17)	N2—C3—N1	122.56 (17)
N5—C7—C5	102.69 (14)	N3—C4—H4A	109.5
N5—C7—H7A	111.2	N3—C4—H4B	109.5
C5—C7—H7A	111.2	H4A—C4—H4B	109.5
N5—C7—H7B	111.2	N3—C4—H4C	109.5
C5—C7—H7B	111.2	H4A—C4—H4C	109.5
H7A—C7—H7B	109.1	H4B—C4—H4C	109.5
N5—C8—H8A	109.5
Cl1—Cd1—O1—C5	79.99 (16)	O1—C5—C7—N5	179.62 (18)
Cl4—Cd1—O1—C5	−38.13 (16)	N4—C5—C7—N5	−0.20 (19)
Cl2—Cd1—O1—C5	−157.67 (17)	C3—N1—C1—O2	172.47 (17)
Cd1—O1—C5—N4	2.7 (3)	C3—N1—C1—C2	−5.74 (19)
Cd1—O1—C5—C7	−177.09 (13)	O2—C1—C2—N3	−172.51 (18)
C6—N4—C5—O1	178.19 (18)	N1—C1—C2—N3	5.63 (18)
C6—N4—C5—C7	−2.0 (2)	C1—C2—N3—C3	−3.83 (19)
C7—N5—C6—N6	179.08 (18)	C1—C2—N3—C4	177.23 (15)
C8—N5—C6—N6	8.7 (3)	C4—N3—C3—N2	−1.6 (3)
C7—N5—C6—N4	−3.8 (2)	C2—N3—C3—N2	179.59 (18)
C8—N5—C6—N4	−174.16 (17)	C4—N3—C3—N1	179.35 (16)
C5—N4—C6—N5	3.7 (2)	C2—N3—C3—N1	0.5 (2)
C5—N4—C6—N6	−179.05 (17)	C1—N1—C3—N3	3.5 (2)
C6—N5—C7—C5	2.43 (19)	C1—N1—C3—N2	−175.66 (17)
C8—N5—C7—C5	173.30 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl3	0.79 (2)	2.41 (2)	3.1840 (16)	168 (2)
N2—H2···Cl3i	0.80 (3)	2.48 (3)	3.273 (2)	170 (3)
N4—H4···Cl4	0.75 (2)	2.70 (2)	3.2967 (17)	139 (2)
N6—H6···Cl2ii	0.88 (3)	2.32 (3)	3.1673 (18)	161 (3)
N2—H22···Cl1	0.90 (2)	2.34 (2)	3.2368 (18)	171 (2)
N6—H66···Cl4iii	0.81 (3)	2.55 (3)	3.2117 (17)	140 (2)

Cd1—Cl1	2.4571 (5)
Cd1—Cl4	2.4596 (4)
Cd1—Cl2	2.4627 (4)
Cd1—Cl3	2.5678 (4)
Cd1—O1	2.6854 (13)

Cl1—Cd1—Cl4	116.512 (15)
Cl1—Cd1—Cl2	120.122 (17)
Cl4—Cd1—Cl2	117.621 (16)
Cl1—Cd1—Cl3	96.649 (15)
Cl4—Cd1—Cl3	98.074 (15)
Cl2—Cd1—Cl3	99.319 (15)
Cl1—Cd1—O1	82.18 (3)
Cl4—Cd1—O1	82.85 (3)
Cl2—Cd1—O1	80.95 (3)
Cl3—Cd1—O1	178.75 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl3	0.79 (2)	2.41 (2)	3.1840 (16)	168 (2)
N2—H2⋯Cl3i	0.80 (3)	2.48 (3)	3.273 (2)	170 (3)
N4—H4⋯Cl4	0.75 (2)	2.70 (2)	3.2967 (17)	139 (2)
N6—H6⋯Cl2ii	0.88 (3)	2.32 (3)	3.1673 (18)	161 (3)
N2—H22⋯Cl1	0.90 (2)	2.34 (2)	3.2368 (18)	171 (2)
N6—H66⋯Cl4iii	0.81 (3)	2.55 (3)	3.2117 (17)	140 (2)

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