Diaqua-bis(8-chloro-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetra-hydro-7H-purinato-κN)copper(II) dihydrate.

The title mononuclear copper(II) complex, [Cu(C(7)H(6)ClN(4)O(2))(2)(H(2)O)(2)]·2H(2)O, based on 8-chloro-theophylline (HCt), has the Cu atom at a center of symmetry in a slightly distorted trans square-planar geometry coordinated by two N atoms of two deprotonated HCt ligands and two O atoms of water mol-ecules. The crystal packing is stabilized by hydrogen bonds involving deprotonated HCt ligands, coordinated water mol-ecules and uncoordinated solvent water mol-ecules.

Related literature

For related literature, see: Halpert et al. (2002 ▶); Antholine et al. (1985 ▶); García-Tojal et al. (1996 ▶); Okabe et al. (1993 ▶); Saryan et al. (1979 ▶); Serafin (1996 ▶); Spealman (1988 ▶); West et al. (1993 ▶); Zhao et al. (2003 ▶).

Experimental

Crystal data

[Cu(C7H6ClN4O2)2(H2O)2]·2H2O

M = 562.82

Triclinic,

a = 8.377 (5) Å

b = 8.533 (8) Å

c = 8.830 (3) Å

α = 67.999 (2)°

β = 64.180 (7)°

γ = 78.388 (6)°

V = 526.2 (6) Å3

Z = 1

Mo Kα radiation

μ = 1.35 mm−1

T = 293 (2) K

0.36 × 0.24 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.685, T max = 0.802

3811 measured reflections

1834 independent reflections

936 reflections with I > 2σ(I)

R int = 0.099

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.102

S = 0.99

1834 reflections

153 parameters

19 restraints

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.66 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680802549X/bg2201sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802549X/bg2201Isup2.hkl

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

[Cu(C7H6Cl1N4O2)2(H2O1)2]·2H2O	Z = 1
Mr = 562.82	F000 = 287
Triclinic, P1	Dx = 1.776 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.377 (5) Å	Cell parameters from 822 reflections
b = 8.533 (8) Å	θ = 2.6–25.0º
c = 8.830 (3) Å	µ = 1.35 mm−1
α = 67.999 (2)º	T = 293 (2) K
β = 64.180 (7)º	Block, green
γ = 78.388 (6)º	0.36 × 0.24 × 0.16 mm
V = 526.2 (6) Å3

Bruker SMART CCD area-detector diffractometer	1834 independent reflections
Radiation source: fine-focus sealed tube	936 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.099
T = 293(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.685, Tmax = 0.802	k = −8→10
3811 measured reflections	l = −10→10

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)] = 0.058	H-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2)]
S = 0.99	(Δ/σ)max = 0.004
1834 reflections	Δρmax = 0.54 e Å−3
153 parameters	Δρmin = −0.66 e Å−3
19 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
Cu1	0.5000	0.0000	1.0000	0.0214 (5)
N1	0.5200 (8)	0.0829 (8)	0.7503 (7)	0.0214 (17)
N2	0.1993 (8)	0.4308 (7)	0.6697 (7)	0.0203 (16)
N3	0.4180 (8)	0.3889 (8)	0.4053 (7)	0.0264 (18)
N4	0.6338 (8)	0.1570 (8)	0.4472 (8)	0.0245 (18)
O1	0.1930 (7)	0.2659 (6)	0.9464 (6)	0.0296 (15)
O2	0.2040 (6)	0.6046 (6)	0.3965 (6)	0.0210 (13)
O3	0.6720 (6)	0.1598 (6)	0.9341 (6)	0.0340 (15)
H3A	0.7154	0.2029	0.8256	0.051*
H3B	0.7376	0.1651	0.9815	0.051*
O4	0.8607 (7)	0.0978 (6)	0.1220 (6)	0.0330 (16)
H4A	0.9578	0.1413	0.0704	0.049*
H4B	0.7868	0.1226	0.2097	0.049*
Cl1	0.8042 (3)	−0.1040 (3)	0.6122 (3)	0.0308 (6)
C1	0.4156 (10)	0.2195 (9)	0.6872 (9)	0.0171 (19)
C2	0.2692 (10)	0.2944 (9)	0.7842 (10)	0.019 (2)
C3	0.2719 (10)	0.4812 (9)	0.4827 (9)	0.0142 (18)
C4	0.4889 (11)	0.2531 (10)	0.5113 (10)	0.022 (2)
C5	0.6432 (10)	0.0543 (9)	0.6041 (10)	0.019 (2)
C6	0.0408 (9)	0.5307 (9)	0.7496 (9)	0.021 (2)
H6A	0.0759	0.6360	0.7389	0.032*
H6B	−0.0203	0.4686	0.8731	0.032*
H6C	−0.0367	0.5527	0.6890	0.032*
C7	0.4918 (9)	0.4281 (9)	0.2102 (8)	0.020 (2)
H7A	0.3980	0.4704	0.1685	0.030*
H7B	0.5465	0.3273	0.1809	0.030*
H7C	0.5788	0.5122	0.1544	0.030*

	U11	U22	U33	U12	U13	U23
Cu1	0.0267 (10)	0.0224 (10)	0.0140 (9)	−0.0032 (8)	−0.0113 (8)	0.0001 (7)
N1	0.019 (4)	0.027 (4)	0.017 (4)	−0.011 (3)	−0.010 (3)	0.001 (3)
N2	0.027 (4)	0.021 (4)	0.009 (3)	−0.004 (3)	−0.004 (3)	−0.003 (3)
N3	0.030 (5)	0.036 (5)	0.011 (4)	−0.006 (4)	−0.004 (3)	−0.008 (3)
N4	0.022 (4)	0.033 (4)	0.012 (4)	−0.006 (3)	−0.002 (3)	−0.003 (3)
O1	0.036 (4)	0.033 (4)	0.014 (3)	−0.006 (3)	−0.007 (3)	−0.003 (3)
O2	0.0205 (16)	0.0215 (16)	0.0201 (15)	0.0010 (9)	−0.0110 (10)	−0.0035 (10)
O3	0.052 (4)	0.038 (4)	0.013 (3)	−0.031 (3)	−0.015 (3)	0.008 (3)
O4	0.027 (4)	0.050 (4)	0.018 (3)	−0.005 (3)	−0.010 (3)	−0.004 (3)
Cl1	0.0279 (15)	0.0291 (15)	0.0273 (13)	0.0002 (11)	−0.0096 (11)	−0.0031 (11)
C1	0.027 (5)	0.014 (5)	0.009 (4)	0.002 (4)	−0.010 (4)	−0.002 (3)
C2	0.019 (2)	0.019 (2)	0.019 (2)	−0.0004 (10)	−0.0083 (12)	−0.0056 (11)
C3	0.014 (2)	0.014 (2)	0.014 (2)	0.0005 (10)	−0.0066 (12)	−0.0031 (11)
C4	0.022 (2)	0.022 (2)	0.022 (2)	−0.0005 (10)	−0.0092 (12)	−0.0064 (12)
C5	0.011 (5)	0.019 (5)	0.028 (5)	−0.002 (4)	−0.002 (4)	−0.014 (4)
C6	0.021 (2)	0.021 (2)	0.020 (2)	0.0002 (10)	−0.0092 (12)	−0.0055 (11)
C7	0.020 (2)	0.020 (2)	0.019 (2)	0.0004 (10)	−0.0088 (12)	−0.0048 (11)

Cu1—O3i	1.934 (5)	O2—C3	1.244 (7)
Cu1—O3	1.934 (5)	O3—H3A	0.8200
Cu1—N1	1.986 (6)	O3—H3B	0.8388
Cu1—N1i	1.986 (6)	O4—H4A	0.8242
N1—C5	1.329 (8)	O4—H4B	0.8243
N1—C1	1.401 (8)	Cl1—C5	1.711 (7)
N2—C3	1.407 (8)	C1—C4	1.333 (9)
N2—C2	1.442 (8)	C1—C2	1.351 (9)
N2—C6	1.472 (8)	C6—H6A	0.9600
N3—C3	1.369 (8)	C6—H6B	0.9600
N3—C4	1.402 (8)	C6—H6C	0.9600
N3—C7	1.479 (7)	C7—H7A	0.9600
N4—C5	1.361 (8)	C7—H7B	0.9600
N4—C4	1.347 (9)	C7—H7C	0.9600
O1—C2	1.234 (8)
O3i—Cu1—O3	180.0 (3)	O1—C2—N2	118.4 (7)
O3i—Cu1—N1	90.5 (2)	C1—C2—N2	110.6 (7)
O3—Cu1—N1	89.5 (2)	O2—C3—N3	123.4 (6)
O3i—Cu1—N1i	89.5 (2)	O2—C3—N2	120.1 (7)
O3—Cu1—N1i	90.5 (2)	N3—C3—N2	116.5 (6)
N1—Cu1—N1i	180.000 (1)	C1—C4—N4	116.5 (7)
C5—N1—C1	104.1 (6)	C1—C4—N3	119.0 (7)
C5—N1—Cu1	131.8 (5)	N4—C4—N3	124.4 (7)
C1—N1—Cu1	122.9 (5)	N1—C5—N4	116.4 (7)
C3—N2—C2	125.4 (6)	N1—C5—Cl1	122.0 (6)
C3—N2—C6	115.4 (6)	N4—C5—Cl1	121.6 (6)
C2—N2—C6	119.2 (6)	N2—C6—H6A	109.5
C3—N3—C4	120.1 (6)	N2—C6—H6B	109.5
C3—N3—C7	118.8 (6)	H6A—C6—H6B	109.5
C4—N3—C7	121.0 (6)	N2—C6—H6C	109.5
C5—N4—C4	98.7 (6)	H6A—C6—H6C	109.5
Cu1—O3—H3A	109.4	H6B—C6—H6C	109.5
Cu1—O3—H3B	132.7	N3—C7—H7A	109.5
H3A—O3—H3B	112.4	N3—C7—H7B	109.5
H4A—O4—H4B	118.2	H7A—C7—H7B	109.5
C4—C1—C2	128.2 (7)	N3—C7—H7C	109.5
C4—C1—N1	104.3 (7)	H7A—C7—H7C	109.5
C2—C1—N1	127.5 (7)	H7B—C7—H7C	109.5
O1—C2—C1	131.0 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2ii	0.82	1.98	2.729 (7)	154
O3—H3B···O4iii	0.84	1.81	2.612 (8)	159
O4—H4A···O1iv	0.82	2.07	2.897 (9)	176
O4—H4B···N4	0.82	2.03	2.839 (8)	170

Cu1—O3	1.934 (5)
Cu1—N1	1.986 (6)

O3i—Cu1—O3	180
O3—Cu1—N1	89.5 (2)
O3—Cu1—N1i	90.5 (2)
N1—Cu1—N1i	180

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2ii	0.82	1.98	2.729 (7)	154
O3—H3B⋯O4iii	0.84	1.81	2.612 (8)	159
O4—H4A⋯O1iv	0.82	2.07	2.897 (9)	176
O4—H4B⋯N4	0.82	2.03	2.839 (8)	170

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