Poly[bis-(μ-2,6-dimethyl-pyridinium-3,5-dicarboxyl-ato-κO:O)copper(II)].

In the title coordination polymer, [Cu(C(9)H(8)NO(4))(2)](n), the Cu atom, located on a twofold rotation axis, is four coordinate in a distorted square-planar environment. Each 2,6-dimethyl-pyridinium-3,5-dicarboxyl-ate anion bridges two Cu atoms, forming a two-dimensional coordination polymer. A three-dimensional supra-molecular network is built from N-H⋯O hydrogen bonds involving the pyridinium NH and the carboxyl COO groups.

Related literature

For the synthesis of 2,6-dimethyl­pyridine-3,5-dicarboxylic acid, see: Checchi et al. (1959 ▶). For the crystal structures of some of its metal complexes, see: Gao et al. (2007 ▶); Shi et al. (2007 ▶); Zeng et al. (2000 ▶, 2002 ▶).

Experimental

Crystal data

[Cu(C9H8N2O4)2]

M = 451.87

Orthorhombic,

a = 8.2003 (16) Å

b = 16.234 (3) Å

c = 13.708 (3) Å

V = 1824.9 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.25 mm−1

T = 291 (2) K

0.26 × 0.24 × 0.19 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.733, T max = 0.801

16747 measured reflections

2097 independent reflections

1754 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.092

S = 1.09

2097 reflections

138 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.29 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035873/ng2511sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035873/ng2511Isup2.hkl

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

[Cu(C9H8N2O4)2]	F000 = 924
Mr = 451.87	Dx = 1.645 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 12587 reflections
a = 8.2003 (16) Å	θ = 3.2–27.5º
b = 16.234 (3) Å	µ = 1.25 mm−1
c = 13.708 (3) Å	T = 291 (2) K
V = 1824.9 (6) Å3	Bluck, black
Z = 4	0.26 × 0.24 × 0.19 mm

Rigaku R-AXIS RAPID diffractometer	2097 independent reflections
Radiation source: fine-focus sealed tube	1754 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.051
T = 291(2) K	θmax = 27.5º
ω scan	θmin = 3.2º
Absorption correction: Multi-scan(ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.733, Tmax = 0.801	k = −21→21
16747 measured reflections	l = −17→17

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)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0491P)2 + 0.9342P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.008
2097 reflections	Δρmax = 0.41 e Å−3
138 parameters	Δρmin = −0.29 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
C1	0.1149 (2)	0.35544 (11)	0.53558 (13)	0.0216 (4)
C2	0.1113 (2)	0.33765 (12)	0.43628 (14)	0.0226 (4)
C3	0.1706 (3)	0.39606 (12)	0.37198 (13)	0.0251 (4)
H1	0.1677	0.3849	0.3055	0.030*
C4	0.2345 (3)	0.47081 (12)	0.40328 (13)	0.0225 (4)
C5	0.2407 (3)	0.48643 (11)	0.50282 (13)	0.0211 (4)
C6	0.0406 (3)	0.25909 (13)	0.39516 (15)	0.0269 (4)
C7	0.2938 (3)	0.53108 (12)	0.32739 (14)	0.0257 (4)
C8	0.3043 (3)	0.56351 (13)	0.54895 (15)	0.0300 (5)
H5	0.2941	0.5595	0.6186	0.045*
H6	0.2427	0.6099	0.5259	0.045*
H7	0.4170	0.5706	0.5320	0.045*
C9	0.0530 (3)	0.30107 (14)	0.61494 (15)	0.0331 (5)
H2	0.1078	0.3142	0.6749	0.050*
H3	0.0736	0.2446	0.5984	0.050*
H4	−0.0621	0.3094	0.6227	0.050*
Cu1	0.0000	0.148168 (18)	0.2500	0.02018 (13)
H8	0.186 (3)	0.4388 (17)	0.621 (2)	0.042 (8)*
N1	0.1800 (2)	0.42800 (10)	0.56291 (12)	0.0225 (4)
O1	−0.0813 (2)	0.22887 (11)	0.43090 (13)	0.0466 (5)
O2	0.1169 (2)	0.23282 (9)	0.32017 (10)	0.0333 (4)
O3	0.2050 (3)	0.54134 (12)	0.25578 (11)	0.0442 (5)
O4	0.4295 (2)	0.56494 (9)	0.34300 (11)	0.0337 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0243 (10)	0.0224 (9)	0.0180 (9)	0.0001 (8)	−0.0003 (7)	0.0006 (7)
C2	0.0248 (10)	0.0226 (9)	0.0203 (9)	−0.0015 (8)	−0.0012 (7)	−0.0027 (7)
C3	0.0331 (11)	0.0271 (10)	0.0152 (8)	−0.0015 (8)	−0.0020 (7)	−0.0029 (7)
C4	0.0283 (10)	0.0217 (9)	0.0175 (8)	−0.0017 (8)	−0.0009 (7)	0.0015 (7)
C5	0.0239 (10)	0.0207 (9)	0.0186 (9)	0.0000 (8)	−0.0020 (7)	0.0002 (7)
C6	0.0319 (11)	0.0239 (10)	0.0250 (10)	−0.0044 (8)	−0.0064 (8)	−0.0013 (8)
C7	0.0382 (12)	0.0203 (9)	0.0186 (9)	0.0020 (9)	0.0036 (8)	0.0015 (7)
C8	0.0399 (12)	0.0254 (10)	0.0246 (10)	−0.0060 (9)	−0.0031 (8)	−0.0051 (8)
C9	0.0442 (13)	0.0325 (11)	0.0225 (10)	−0.0085 (10)	0.0067 (9)	0.0033 (8)
Cu1	0.0283 (2)	0.01488 (19)	0.01735 (19)	0.000	−0.00329 (12)	0.000
N1	0.0294 (9)	0.0249 (8)	0.0132 (7)	−0.0018 (7)	−0.0006 (6)	−0.0012 (6)
O1	0.0439 (11)	0.0449 (10)	0.0511 (10)	−0.0222 (9)	0.0102 (9)	−0.0123 (8)
O2	0.0440 (9)	0.0283 (7)	0.0277 (7)	−0.0087 (7)	−0.0004 (7)	−0.0095 (6)
O3	0.0507 (11)	0.0592 (12)	0.0228 (8)	−0.0022 (9)	−0.0051 (7)	0.0161 (7)
O4	0.0442 (10)	0.0279 (8)	0.0290 (8)	−0.0094 (7)	0.0034 (7)	0.0081 (6)

C1—N1	1.346 (3)	C7—O4	1.259 (3)
C1—C2	1.392 (3)	C8—H5	0.9600
C1—C9	1.490 (3)	C8—H6	0.9600
C2—C3	1.383 (3)	C8—H7	0.9600
C2—C6	1.510 (3)	C9—H2	0.9600
C3—C4	1.390 (3)	C9—H3	0.9600
C3—H1	0.9300	C9—H4	0.9600
C4—C5	1.389 (3)	Cu1—O2	1.9322 (15)
C4—C7	1.509 (3)	Cu1—O2i	1.9322 (15)
C5—N1	1.351 (2)	Cu1—O4ii	1.9455 (15)
C5—C8	1.496 (3)	Cu1—O4iii	1.9455 (15)
C6—O1	1.216 (3)	N1—H8	0.82 (3)
C6—O2	1.277 (3)	O4—Cu1iv	1.9455 (15)
C7—O3	1.234 (3)
N1—C1—C2	117.53 (17)	C5—C8—H6	109.5
N1—C1—C9	116.75 (17)	H5—C8—H6	109.5
C2—C1—C9	125.72 (18)	C5—C8—H7	109.5
C3—C2—C1	118.26 (17)	H5—C8—H7	109.5
C3—C2—C6	118.44 (17)	H6—C8—H7	109.5
C1—C2—C6	123.26 (17)	C1—C9—H2	109.5
C2—C3—C4	122.31 (17)	C1—C9—H3	109.5
C2—C3—H1	118.8	H2—C9—H3	109.5
C4—C3—H1	118.8	C1—C9—H4	109.5
C5—C4—C3	118.47 (17)	H2—C9—H4	109.5
C5—C4—C7	123.17 (17)	H3—C9—H4	109.5
C3—C4—C7	118.36 (17)	O2—Cu1—O2i	89.32 (10)
N1—C5—C4	117.21 (17)	O2—Cu1—O4ii	165.38 (7)
N1—C5—C8	117.25 (16)	O2i—Cu1—O4ii	91.17 (7)
C4—C5—C8	125.51 (17)	O2—Cu1—O4iii	91.17 (7)
O1—C6—O2	126.3 (2)	O2i—Cu1—O4iii	165.38 (7)
O1—C6—C2	120.40 (19)	O4ii—Cu1—O4iii	92.03 (10)
O2—C6—C2	113.20 (18)	C1—N1—C5	126.19 (16)
O3—C7—O4	126.7 (2)	C1—N1—H8	119 (2)
O3—C7—C4	116.5 (2)	C5—N1—H8	115 (2)
O4—C7—C4	116.80 (18)	C6—O2—Cu1	113.26 (14)
C5—C8—H5	109.5	C7—O4—Cu1iv	117.02 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H8···O3v	0.82 (3)	1.88 (3)	2.698 (2)	177 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H8⋯O3i	0.82 (3)	1.88 (3)	2.698 (2)	177 (3)

Symmetry code: (i) .