Bis(4-carb-oxy-pyridine-2-carboxyl-ato-κN,O)copper(II) dimethyl sulfoxide disolvate.

In the title complex, [Cu(C(7)H(4)NO(4))(2)]·2C(2)H(6)OS, the Cu(II) atom is situated on an inversion centre and is N,O-chelated by two monoanionic 4-carb-oxy-pyridine-2-carboxyl-ate ligands in a slightly distorted square-planar coordination geometry. The dimethyl sulfoxide solvent mol-ecules and Cu(II) complex mol-ecules are linked by O-H⋯O hydrogen bonding. In addition, C-H⋯O contacts and π-π inter-actions [centroid-centroid distance = 3.590 (1) Å] occur.

Related literature

For the design and synthesis of coordination compounds and complexes derived from pyridine-2,4-dicarb­oxy­lic acid, see: Aghabozorg et al. (2008 ▶); Noro et al. (2005 ▶).

Experimental

Crystal data

[Cu(C7H4NO4)2]·2C2H6OS

M = 552.05

Triclinic,

a = 6.8831 (14) Å

b = 7.5218 (15) Å

c = 11.719 (2) Å

α = 102.95 (3)°

β = 91.86 (3)°

γ = 111.12 (3)°

V = 547.3 (2) Å3

Z = 1

Mo Kα radiation

μ = 1.25 mm−1

T = 298 K

0.2 × 0.10 × 0.05 mm

Data collection

Stoe IPDS II diffractometer

6125 measured reflections

2928 independent reflections

2428 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.092

S = 1.08

2928 reflections

157 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.30 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811003424/bt5466sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003424/bt5466Isup2.hkl

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

[Cu(C7H4NO4)2]·2C2H6OS	Z = 1
Mr = 552.05	F(000) = 283
Triclinic, P1	Dx = 1.675 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8831 (14) Å	Cell parameters from 2928 reflections
b = 7.5218 (15) Å	θ = 3.0–29.1°
c = 11.719 (2) Å	µ = 1.25 mm−1
α = 102.95 (3)°	T = 298 K
β = 91.86 (3)°	Plate, purple
γ = 111.12 (3)°	0.2 × 0.1 × 0.05 mm
V = 547.3 (2) Å3

Stoe IPDS II diffractometer	2428 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
graphite	θmax = 29.1°, θmin = 3.0°
Detector resolution: 0.15 mm pixels mm-1	h = −9→9
rotation method scans	k = −10→10
6125 measured reflections	l = −16→15
2928 independent reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0365P)2 + 0.2725P] where P = (Fo2 + 2Fc2)/3
2928 reflections	(Δ/σ)max = 0.002
157 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.30 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	0.7477 (3)	0.7579 (3)	0.25725 (15)	0.0572 (5)
S1	0.74093 (10)	0.67910 (10)	0.12483 (5)	0.04660 (16)
Cu1	0.5000	0.0000	0.5000	0.03607 (12)
O1	0.3689 (2)	0.0279 (3)	0.36230 (14)	0.0448 (4)
C6	0.4947 (3)	0.1284 (4)	0.30111 (19)	0.0383 (5)
C2	0.8846 (3)	0.3107 (3)	0.29424 (18)	0.0362 (4)
H2	0.8551	0.3418	0.2249	0.043*
C1	0.7250 (3)	0.2025 (3)	0.34780 (18)	0.0339 (4)
O2	0.4440 (3)	0.1668 (3)	0.21140 (16)	0.0540 (5)
N1	0.7628 (3)	0.1553 (3)	0.44860 (15)	0.0331 (4)
C7	1.2654 (4)	0.4892 (4)	0.28672 (19)	0.0387 (5)
C5	0.9603 (3)	0.2151 (3)	0.49832 (18)	0.0358 (4)
H5	0.9857	0.1825	0.5678	0.043*
C4	1.1283 (3)	0.3242 (3)	0.44914 (19)	0.0368 (4)
H4	1.2648	0.3647	0.4853	0.044*
C3	1.0910 (3)	0.3727 (3)	0.34541 (19)	0.0355 (4)
O3	1.4430 (3)	0.5841 (3)	0.35694 (15)	0.0481 (4)
O4	1.2395 (3)	0.4936 (3)	0.18477 (15)	0.0526 (5)
C8	0.6304 (5)	0.8138 (5)	0.0578 (2)	0.0612 (7)
H8A	0.4882	0.7847	0.0744	0.092*
H8B	0.6323	0.7782	−0.0260	0.092*
H8C	0.7104	0.9522	0.0883	0.092*
C9	1.0046 (5)	0.7850 (6)	0.0982 (3)	0.0713 (9)
H9A	1.0577	0.9246	0.1323	0.107*
H9B	1.0111	0.7597	0.0147	0.107*
H9C	1.0879	0.7280	0.1332	0.107*
H3	1.538 (6)	0.645 (5)	0.320 (3)	0.076 (11)*

	U11	U22	U33	U12	U13	U23
O5	0.0428 (9)	0.0775 (13)	0.0357 (9)	0.0011 (9)	0.0015 (7)	0.0208 (9)
S1	0.0437 (3)	0.0481 (4)	0.0400 (3)	0.0059 (3)	0.0025 (2)	0.0150 (3)
Cu1	0.03021 (19)	0.0481 (2)	0.03117 (19)	0.01310 (16)	0.00208 (14)	0.01565 (16)
O1	0.0315 (8)	0.0623 (11)	0.0408 (8)	0.0127 (7)	−0.0007 (6)	0.0226 (8)
C6	0.0351 (11)	0.0454 (12)	0.0332 (10)	0.0140 (9)	−0.0016 (8)	0.0110 (9)
C2	0.0378 (11)	0.0411 (11)	0.0286 (9)	0.0131 (9)	−0.0010 (8)	0.0105 (8)
C1	0.0341 (10)	0.0378 (11)	0.0288 (9)	0.0133 (8)	−0.0010 (8)	0.0077 (8)
O2	0.0437 (9)	0.0719 (12)	0.0461 (10)	0.0140 (9)	−0.0067 (7)	0.0293 (9)
N1	0.0336 (8)	0.0394 (9)	0.0272 (8)	0.0142 (7)	0.0019 (6)	0.0096 (7)
C7	0.0362 (11)	0.0479 (13)	0.0343 (10)	0.0167 (10)	0.0045 (8)	0.0134 (9)
C5	0.0359 (10)	0.0437 (12)	0.0296 (9)	0.0161 (9)	−0.0002 (8)	0.0117 (8)
C4	0.0321 (10)	0.0452 (12)	0.0324 (10)	0.0149 (9)	−0.0008 (8)	0.0089 (9)
C3	0.0354 (10)	0.0402 (11)	0.0302 (9)	0.0146 (9)	0.0032 (8)	0.0072 (8)
O3	0.0342 (8)	0.0658 (12)	0.0363 (8)	0.0073 (8)	0.0045 (7)	0.0169 (8)
O4	0.0450 (10)	0.0746 (13)	0.0379 (9)	0.0159 (9)	0.0047 (7)	0.0249 (9)
C8	0.0671 (18)	0.079 (2)	0.0426 (14)	0.0313 (16)	0.0007 (13)	0.0185 (14)
C9	0.0473 (16)	0.109 (3)	0.0604 (18)	0.0251 (17)	0.0136 (14)	0.0325 (18)

O5—S1	1.5247 (19)	C7—O4	1.212 (3)
S1—C8	1.760 (3)	C7—O3	1.313 (3)
S1—C9	1.770 (3)	C7—C3	1.499 (3)
Cu1—O1	1.9123 (16)	C5—C4	1.384 (3)
Cu1—O1i	1.9123 (16)	C5—H5	0.9300
Cu1—N1	1.9657 (19)	C4—C3	1.387 (3)
Cu1—N1i	1.9657 (19)	C4—H4	0.9300
O1—C6	1.284 (3)	O3—H3	0.84 (4)
C6—O2	1.223 (3)	C8—H8A	0.9600
C6—C1	1.514 (3)	C8—H8B	0.9600
C2—C1	1.376 (3)	C8—H8C	0.9600
C2—C3	1.392 (3)	C9—H9A	0.9600
C2—H2	0.9300	C9—H9B	0.9600
C1—N1	1.351 (3)	C9—H9C	0.9600
N1—C5	1.334 (3)
O5—S1—C8	105.52 (14)	O3—C7—C3	113.21 (19)
O5—S1—C9	104.03 (14)	N1—C5—C4	121.70 (19)
C8—S1—C9	99.68 (17)	N1—C5—H5	119.2
O1—Cu1—O1i	180.00 (5)	C4—C5—H5	119.2
O1—Cu1—N1	84.57 (7)	C5—C4—C3	119.3 (2)
O1i—Cu1—N1	95.43 (7)	C5—C4—H4	120.4
O1—Cu1—N1i	95.43 (7)	C3—C4—H4	120.4
O1i—Cu1—N1i	84.57 (7)	C4—C3—C2	118.7 (2)
N1—Cu1—N1i	180.0	C4—C3—C7	122.2 (2)
C6—O1—Cu1	115.22 (14)	C2—C3—C7	119.08 (19)
O2—C6—O1	125.9 (2)	C7—O3—H3	111 (2)
O2—C6—C1	119.3 (2)	S1—C8—H8A	109.5
O1—C6—C1	114.78 (18)	S1—C8—H8B	109.5
C1—C2—C3	118.97 (19)	H8A—C8—H8B	109.5
C1—C2—H2	120.5	S1—C8—H8C	109.5
C3—C2—H2	120.5	H8A—C8—H8C	109.5
N1—C1—C2	121.90 (19)	H8B—C8—H8C	109.5
N1—C1—C6	114.33 (19)	S1—C9—H9A	109.5
C2—C1—C6	123.77 (18)	S1—C9—H9B	109.5
C5—N1—C1	119.41 (19)	H9A—C9—H9B	109.5
C5—N1—Cu1	129.51 (15)	S1—C9—H9C	109.5
C1—N1—Cu1	111.07 (14)	H9A—C9—H9C	109.5
O4—C7—O3	124.8 (2)	H9B—C9—H9C	109.5
O4—C7—C3	122.0 (2)
N1—Cu1—O1—C6	−0.79 (18)	O1i—Cu1—N1—C5	0.0 (2)
N1i—Cu1—O1—C6	179.21 (18)	O1—Cu1—N1—C1	−0.07 (15)
Cu1—O1—C6—O2	−178.7 (2)	O1i—Cu1—N1—C1	179.93 (15)
Cu1—O1—C6—C1	1.4 (3)	C1—N1—C5—C4	−0.1 (3)
C3—C2—C1—N1	0.1 (3)	Cu1—N1—C5—C4	179.81 (16)
C3—C2—C1—C6	179.5 (2)	N1—C5—C4—C3	−0.1 (3)
O2—C6—C1—N1	178.6 (2)	C5—C4—C3—C2	0.4 (3)
O1—C6—C1—N1	−1.5 (3)	C5—C4—C3—C7	−179.5 (2)
O2—C6—C1—C2	−0.8 (4)	C1—C2—C3—C4	−0.4 (3)
O1—C6—C1—C2	179.2 (2)	C1—C2—C3—C7	179.5 (2)
C2—C1—N1—C5	0.1 (3)	O4—C7—C3—C4	162.8 (2)
C6—C1—N1—C5	−179.27 (19)	O3—C7—C3—C4	−17.7 (3)
C2—C1—N1—Cu1	−179.83 (17)	O4—C7—C3—C2	−17.1 (4)
C6—C1—N1—Cu1	0.8 (2)	O3—C7—C3—C2	162.4 (2)
O1—Cu1—N1—C5	180.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O5ii	0.84 (4)	1.68 (4)	2.518 (3)	173 (4)
C4—H4···O3iii	0.93	2.55	3.427 (3)	158
C5—H5···O5iv	0.93	2.55	3.370 (3)	147
C8—H8B···O2v	0.96	2.38	3.223 (3)	147
C9—H9C···O4	0.96	2.51	3.448 (4)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O5i	0.84 (4)	1.68 (4)	2.518 (3)	173 (4)
C4—H4⋯O3ii	0.93	2.55	3.427 (3)	158
C5—H5⋯O5iii	0.93	2.55	3.370 (3)	147
C8—H8B⋯O2iv	0.96	2.38	3.223 (3)	147
C9—H9C⋯O4	0.96	2.51	3.448 (4)	164

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