Poly[[(N,N-dimethyl-formamide-κO)(μ(3)-pyrazine-2,3-dicarboxyl-ato-κN,O:O:O)copper(II)] monohydrate].

In the title compound, {[Cu(C(6)H(2)N(2)O(4))(C(3)H(7)NO)]·H(2)O}(n), the Cu(II) atom is coordinated by an N,O-bidentate pyrazine-2,3-dicarboxyl-ate (pzdc) dianion, two O atoms from two other pzdc anions and one O atom from the dimethlyformamide ligand, forming a distorted square-pyramidal CuNO(4) geometry. The polymeric character of the structure is established by the formation of layers parallel to (100) via bridging pzdc ligands. O-H⋯O hydrogen bonding between water mol-ecules and uncoordinated carboxyl-ate O atoms leads to additional stabilization of the structure.

Related literature

For related structures with the pyrazine-2,3-dicarboxyl­ate (pzdc) dianion, see: Hua & Liu (2009 ▶); Konar et al. (2004 ▶); Li et al. (2004 ▶); Lin et al. (2009 ▶); Tombul & Guven (2009 ▶); Wang et al. (2008 ▶); Xiang et al. (2004 ▶); Xu et al. (2008 ▶).

Experimental

Crystal data

[Cu(C6H2N2O4)(C3H7NO)]·H2O

M = 320.75

Monoclinic,

a = 10.1656 (5) Å

b = 13.6310 (8) Å

c = 9.1461 (2) Å

β = 91.430 (2)°

V = 1266.96 (10) Å3

Z = 4

Mo Kα radiation

μ = 1.75 mm−1

T = 298 K

0.39 × 0.10 × 0.06 mm

Data collection

Bruker APEX area-detector diffractometer

Absorption correction: integration (SADABS; Bruker, 2002 ▶) T min = 0.549, T max = 0.902

6222 measured reflections

2283 independent reflections

1600 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.115

S = 0.98

2283 reflections

180 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809051332/wm2283sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051332/wm2283Isup2.hkl

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

[Cu(C6H2N2O4)(C3H7NO)]·H2O	F(000) = 652
Mr = 320.75	Dx = 1.682 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1111 reflections
a = 10.1656 (5) Å	θ = 2.5–22.4°
b = 13.6310 (8) Å	µ = 1.75 mm−1
c = 9.1461 (2) Å	T = 298 K
β = 91.430 (2)°	Prism, blue
V = 1266.96 (10) Å3	0.39 × 0.10 × 0.06 mm
Z = 4

Bruker APEX area-detector diffractometer	2283 independent reflections
Radiation source: fine-focus sealed tube	1600 reflections with I > 2σ(I)
graphite	Rint = 0.058
phi and ω scans	θmax = 25.3°, θmin = 2.0°
Absorption correction: integration (SADABS; Bruker, 2002)	h = −8→12
Tmin = 0.549, Tmax = 0.902	k = −16→16
6222 measured reflections	l = −10→10

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ2(Fo2) + (0.0482P)2] where P = (Fo2 + 2Fc2)/3
2283 reflections	(Δ/σ)max < 0.001
180 parameters	Δρmax = 0.48 e Å−3
3 restraints	Δρmin = −0.33 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
Cu1	0.59999 (5)	0.58784 (3)	0.07521 (6)	0.0402 (2)
O1	0.5775 (3)	0.8747 (2)	0.1085 (4)	0.0526 (10)
O2	0.6295 (3)	0.7254 (2)	0.0382 (4)	0.0463 (9)
O3	0.4380 (3)	0.9489 (2)	0.3914 (3)	0.0386 (8)
O4	0.2821 (3)	0.9362 (2)	0.2189 (4)	0.0511 (9)
O5	0.7494 (3)	0.5510 (2)	−0.0435 (4)	0.0503 (9)
O6	0.2218 (5)	0.1287 (3)	0.1467 (7)	0.121 (2)
N1	0.4710 (3)	0.6417 (2)	0.2162 (4)	0.0298 (8)
N2	0.3001 (3)	0.7442 (2)	0.3914 (4)	0.0402 (9)
N3	0.9066 (4)	0.5894 (4)	−0.2048 (5)	0.0655 (13)
C1	0.5654 (4)	0.7859 (3)	0.1145 (5)	0.0331 (10)
C2	0.4684 (4)	0.7404 (3)	0.2158 (4)	0.0279 (9)
C3	0.3821 (4)	0.7913 (3)	0.3018 (5)	0.0316 (10)
C4	0.3064 (4)	0.6467 (3)	0.3912 (5)	0.0420 (12)
H4	0.2516	0.6118	0.4523	0.050*
C5	0.3912 (4)	0.5951 (3)	0.3039 (5)	0.0381 (11)
H5	0.3920	0.5269	0.3071	0.046*
C6	0.3670 (4)	0.9018 (3)	0.3005 (5)	0.0352 (10)
C7	0.8054 (5)	0.6097 (4)	−0.1238 (6)	0.0554 (14)
H7	0.7732	0.6735	−0.1271	0.066*
C8	0.9664 (6)	0.6630 (5)	−0.2983 (8)	0.112 (3)
H8A	0.9216	0.7244	−0.2874	0.168*
H8B	0.9593	0.6421	−0.3985	0.168*
H8C	1.0575	0.6707	−0.2706	0.168*
C9	0.9607 (6)	0.4924 (5)	−0.2062 (7)	0.092 (2)
H9A	1.0486	0.4937	−0.1655	0.137*
H9B	0.9624	0.4688	−0.3051	0.137*
H9C	0.9073	0.4496	−0.1491	0.137*
H6A	0.277 (5)	0.148 (4)	0.089 (6)	0.110*
H6B	0.219 (6)	0.0685 (9)	0.155 (7)	0.110*

	U11	U22	U33	U12	U13	U23
Cu1	0.0472 (4)	0.0182 (3)	0.0560 (4)	0.0032 (2)	0.0188 (3)	0.0026 (3)
O1	0.075 (2)	0.0191 (15)	0.065 (3)	−0.0083 (15)	0.029 (2)	−0.0011 (16)
O2	0.0559 (19)	0.0221 (15)	0.062 (2)	−0.0013 (14)	0.0282 (17)	0.0013 (16)
O3	0.0467 (17)	0.0189 (14)	0.050 (2)	−0.0034 (13)	0.0072 (16)	−0.0062 (15)
O4	0.060 (2)	0.0361 (18)	0.057 (2)	0.0112 (16)	−0.0027 (19)	−0.0003 (17)
O5	0.047 (2)	0.0345 (17)	0.070 (3)	0.0050 (15)	0.0268 (18)	0.0034 (17)
O6	0.102 (4)	0.071 (3)	0.192 (6)	0.010 (3)	0.078 (4)	0.054 (4)
N1	0.0353 (19)	0.0157 (17)	0.039 (2)	−0.0021 (14)	0.0026 (17)	0.0003 (16)
N2	0.049 (2)	0.029 (2)	0.043 (2)	−0.0043 (17)	0.0103 (19)	−0.0032 (18)
N3	0.041 (2)	0.083 (3)	0.074 (4)	0.010 (2)	0.021 (2)	0.004 (3)
C1	0.040 (2)	0.025 (2)	0.034 (3)	−0.0004 (19)	0.008 (2)	−0.002 (2)
C2	0.036 (2)	0.019 (2)	0.029 (3)	−0.0042 (17)	−0.0021 (19)	−0.0008 (18)
C3	0.038 (2)	0.025 (2)	0.032 (3)	−0.0013 (18)	−0.001 (2)	−0.0019 (19)
C4	0.052 (3)	0.030 (2)	0.045 (3)	−0.010 (2)	0.011 (2)	0.002 (2)
C5	0.050 (3)	0.021 (2)	0.044 (3)	−0.004 (2)	0.007 (2)	0.000 (2)
C6	0.039 (2)	0.026 (2)	0.041 (3)	0.004 (2)	0.014 (2)	0.004 (2)
C7	0.043 (3)	0.053 (3)	0.070 (4)	0.009 (2)	0.005 (3)	−0.007 (3)
C8	0.072 (4)	0.144 (7)	0.121 (7)	0.014 (4)	0.049 (4)	0.053 (5)
C9	0.062 (4)	0.098 (5)	0.116 (6)	0.011 (4)	0.030 (4)	−0.050 (4)

Cu1—O2	1.930 (3)	N2—C3	1.346 (5)
Cu1—O5	1.954 (3)	N3—C7	1.313 (6)
Cu1—O3i	1.958 (3)	N3—C9	1.432 (6)
Cu1—N1	2.002 (3)	N3—C8	1.460 (7)
Cu1—O3ii	2.378 (3)	C1—C2	1.504 (5)
O1—C1	1.218 (5)	C2—C3	1.380 (5)
O2—C1	1.271 (5)	C3—C6	1.515 (5)
O3—C6	1.263 (5)	C4—C5	1.381 (6)
O3—Cu1iii	1.958 (3)	C4—H4	0.9300
O3—Cu1iv	2.378 (3)	C5—H5	0.9300
O4—C6	1.220 (5)	C7—H7	0.9300
O5—C7	1.235 (6)	C8—H8A	0.9600
O6—H6A	0.82 (5)	C8—H8B	0.9600
O6—H6B	0.82 (5)	C8—H8C	0.9600
N1—C5	1.318 (5)	C9—H9A	0.9600
N1—C2	1.344 (4)	C9—H9B	0.9600
N2—C4	1.331 (5)	C9—H9C	0.9600
O2—Cu1—O5	91.48 (13)	C3—C2—C1	125.4 (4)
O2—Cu1—O3i	177.39 (13)	N2—C3—C2	121.3 (4)
O5—Cu1—O3i	89.82 (13)	N2—C3—C6	114.5 (4)
O2—Cu1—N1	82.17 (12)	C2—C3—C6	124.2 (4)
O5—Cu1—N1	169.37 (13)	N2—C4—C5	122.6 (4)
O3i—Cu1—N1	96.87 (12)	N2—C4—H4	118.7
O2—Cu1—O3ii	100.87 (12)	C5—C4—H4	118.7
O5—Cu1—O3ii	94.99 (12)	N1—C5—C4	120.6 (4)
O3i—Cu1—O3ii	76.75 (12)	N1—C5—H5	119.7
N1—Cu1—O3ii	94.57 (12)	C4—C5—H5	119.7
C1—O2—Cu1	116.7 (3)	O4—C6—O3	126.2 (4)
C6—O3—Cu1iii	118.9 (3)	O4—C6—C3	117.2 (4)
C6—O3—Cu1iv	137.1 (3)	O3—C6—C3	116.4 (4)
Cu1iii—O3—Cu1iv	103.25 (12)	O5—C7—N3	125.4 (5)
C7—O5—Cu1	122.7 (3)	O5—C7—H7	117.3
H6A—O6—H6B	113.5 (19)	N3—C7—H7	117.3
C5—N1—C2	118.1 (4)	N3—C8—H8A	109.5
C5—N1—Cu1	129.7 (3)	N3—C8—H8B	109.5
C2—N1—Cu1	112.2 (3)	H8A—C8—H8B	109.5
C4—N2—C3	116.4 (4)	N3—C8—H8C	109.5
C7—N3—C9	120.4 (5)	H8A—C8—H8C	109.5
C7—N3—C8	121.9 (5)	H8B—C8—H8C	109.5
C9—N3—C8	117.6 (5)	N3—C9—H9A	109.5
O1—C1—O2	124.5 (4)	N3—C9—H9B	109.5
O1—C1—C2	120.4 (4)	H9A—C9—H9B	109.5
O2—C1—C2	115.1 (3)	N3—C9—H9C	109.5
N1—C2—C3	121.0 (4)	H9A—C9—H9C	109.5
N1—C2—C1	113.7 (3)	H9B—C9—H9C	109.5
O5—Cu1—O2—C1	−169.1 (3)	O1—C1—C2—C3	3.7 (7)
O3i—Cu1—O2—C1	71 (3)	O2—C1—C2—C3	−175.6 (4)
N1—Cu1—O2—C1	2.3 (3)	C4—N2—C3—C2	−0.4 (6)
O3ii—Cu1—O2—C1	95.5 (3)	C4—N2—C3—C6	177.3 (4)
O2—Cu1—O5—C7	−11.7 (4)	N1—C2—C3—N2	1.5 (6)
O3i—Cu1—O5—C7	166.0 (4)	C1—C2—C3—N2	−178.8 (4)
N1—Cu1—O5—C7	−64.7 (9)	N1—C2—C3—C6	−176.0 (4)
O3ii—Cu1—O5—C7	89.4 (4)	C1—C2—C3—C6	3.7 (7)
O2—Cu1—N1—C5	179.2 (4)	C3—N2—C4—C5	−0.5 (6)
O5—Cu1—N1—C5	−127.0 (7)	C2—N1—C5—C4	0.8 (6)
O3i—Cu1—N1—C5	1.7 (4)	Cu1—N1—C5—C4	−178.4 (3)
O3ii—Cu1—N1—C5	78.9 (4)	N2—C4—C5—N1	0.3 (7)
O2—Cu1—N1—C2	0.1 (3)	Cu1iii—O3—C6—O4	7.2 (6)
O5—Cu1—N1—C2	53.8 (8)	Cu1iv—O3—C6—O4	175.4 (3)
O3i—Cu1—N1—C2	−177.5 (3)	Cu1iii—O3—C6—C3	−167.7 (3)
O3ii—Cu1—N1—C2	−100.3 (3)	Cu1iv—O3—C6—C3	0.5 (6)
Cu1—O2—C1—O1	176.6 (4)	N2—C3—C6—O4	−84.7 (5)
Cu1—O2—C1—C2	−4.1 (5)	C2—C3—C6—O4	92.9 (5)
C5—N1—C2—C3	−1.6 (6)	N2—C3—C6—O3	90.7 (4)
Cu1—N1—C2—C3	177.6 (3)	C2—C3—C6—O3	−91.7 (5)
C5—N1—C2—C1	178.7 (4)	Cu1—O5—C7—N3	179.4 (4)
Cu1—N1—C2—C1	−2.1 (4)	C9—N3—C7—O5	0.6 (9)
O1—C1—C2—N1	−176.6 (4)	C8—N3—C7—O5	179.3 (6)
O2—C1—C2—N1	4.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6B···O4v	0.82 (5)	2.00 (3)	2.771 (5)	156 (7)
O6—H6A···O1vi	0.82 (5)	2.38 (3)	3.138 (6)	153 (5)
O6—H6A···O2vi	0.82 (5)	2.30 (3)	3.037 (5)	149 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6B⋯O4i	0.82 (5)	2.00 (3)	2.771 (5)	156 (7)
O6—H6A⋯O1ii	0.82 (5)	2.38 (3)	3.138 (6)	153 (5)
O6—H6A⋯O2ii	0.82 (5)	2.30 (3)	3.037 (5)	149 (5)

Symmetry codes: (i) ; (ii) .