catena-Poly[[[dipyridine-copper(II)]-μ-2,3,5,6-tetra-methyl-benzene-1,4-di-carboxyl-ato] monohydrate].

In the title complex, {[Cu(C(12)H(12)O(4))(C(5)H(5)N)(2)]·H(2)O}(n), the Cu(II) ion lies on an inversion center and is coordinated by two O atoms from two 2,3,5,6-tetra-methyl-benzene-1,4-dicarboxyl-ate (TBDC) ligands and two N atoms from two pyridine ligands in a slightly distorted square-planar environment. The TBDC ligands act as bridging ligands, forming chains along [110]. These chains are further linked into a two-dimensional network via inter-molecular O-H⋯O hydrogen bonds. The solvent water mol-ecule lies on a twofold rotation axis.

Related literature

For related structures, see: Chun et al. (2005 ▶); Diniz et al. (2002 ▶).

Experimental

Crystal data

[Cu(C12H12O4)(C5H5N)2]·H2O

M = 459.98

Monoclinic,

a = 13.3280 (8) Å

b = 17.1434 (11) Å

c = 10.7390 (7) Å

β = 108.481 (1)°

V = 2327.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.97 mm−1

T = 298 K

0.15 × 0.10 × 0.08 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.868, T max = 0.926

6747 measured reflections

2594 independent reflections

2283 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.086

S = 1.06

2594 reflections

142 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810036913/lh5099sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036913/lh5099Isup2.hkl

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

[Cu(C12H12O4)(C5H5N)2]·H2O	F(000) = 956
Mr = 459.98	Dx = 1.313 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3713 reflections
a = 13.3280 (8) Å	θ = 2.4–27.5°
b = 17.1434 (11) Å	µ = 0.97 mm−1
c = 10.7390 (7) Å	T = 298 K
β = 108.481 (1)°	Block, blue
V = 2327.2 (3) Å3	0.15 × 0.10 × 0.08 mm
Z = 4

Bruker SMART CCD diffractometer	2594 independent reflections
Radiation source: fine-focus sealed tube	2283 reflections with I > 2σ(I)
graphite	Rint = 0.017
φ and ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADBAS; Sheldrick, 1996)	h = −17→10
Tmin = 0.868, Tmax = 0.926	k = −19→21
6747 measured reflections	l = −10→13

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0467P)2 + 1.775P] where P = (Fo2 + 2Fc2)/3
2594 reflections	(Δ/σ)max < 0.001
142 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.31 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	0.0000	0.0000	0.0000	0.02763 (11)
O2	0.07772 (9)	0.07930 (7)	−0.06903 (12)	0.0326 (3)
N1	−0.12716 (11)	0.06855 (8)	−0.04454 (14)	0.0313 (3)
O1	0.10913 (11)	0.10867 (8)	0.14011 (13)	0.0418 (3)
C1	0.12054 (13)	0.12134 (9)	0.03160 (17)	0.0294 (3)
C2	0.18792 (13)	0.18884 (9)	0.01433 (16)	0.0289 (3)
C3	0.13967 (13)	0.25988 (10)	−0.03235 (17)	0.0312 (4)
C5	0.29738 (13)	0.17762 (10)	0.04732 (17)	0.0315 (4)
C11	−0.17376 (16)	0.08364 (12)	0.0463 (2)	0.0416 (4)
H11	−0.1455	0.0619	0.1294	0.050*
C7	−0.16747 (16)	0.10076 (13)	−0.1635 (2)	0.0451 (5)
H7	−0.1352	0.0910	−0.2270	0.054*
C4	0.02162 (15)	0.26957 (12)	−0.0624 (2)	0.0474 (5)
H4A	−0.0085	0.2213	−0.0462	0.071*
H4B	−0.0097	0.2840	−0.1528	0.071*
H4C	0.0081	0.3096	−0.0073	0.071*
C6	0.34512 (16)	0.09915 (12)	0.0956 (3)	0.0512 (5)
H6A	0.2904	0.0640	0.1001	0.077*
H6B	0.3961	0.1048	0.1813	0.077*
H6C	0.3793	0.0788	0.0361	0.077*
C9	−0.3036 (2)	0.16249 (18)	−0.1002 (3)	0.0691 (7)
H9	−0.3636	0.1938	−0.1193	0.083*
C10	−0.2619 (2)	0.13013 (15)	0.0210 (3)	0.0598 (6)
H10	−0.2928	0.1394	0.0861	0.072*
C8	−0.2556 (2)	0.14817 (16)	−0.1942 (2)	0.0634 (7)
H8	−0.2823	0.1702	−0.2774	0.076*
O01	0.0000	0.21858 (15)	0.2500	0.0601 (6)
H1A	0.040 (2)	0.1861 (19)	0.216 (3)	0.094 (11)*

	U11	U22	U33	U12	U13	U23
Cu1	0.02676 (16)	0.02207 (16)	0.03625 (18)	−0.00754 (10)	0.01309 (12)	0.00071 (10)
O2	0.0348 (6)	0.0276 (6)	0.0381 (7)	−0.0120 (5)	0.0153 (5)	−0.0013 (5)
N1	0.0316 (7)	0.0265 (7)	0.0372 (8)	−0.0057 (6)	0.0128 (6)	−0.0004 (6)
O1	0.0521 (8)	0.0389 (7)	0.0396 (7)	−0.0136 (6)	0.0222 (6)	0.0006 (6)
C1	0.0286 (8)	0.0235 (8)	0.0385 (9)	−0.0048 (6)	0.0140 (7)	0.0024 (6)
C2	0.0308 (8)	0.0242 (8)	0.0332 (8)	−0.0089 (6)	0.0121 (6)	−0.0012 (6)
C3	0.0280 (8)	0.0278 (8)	0.0382 (9)	−0.0059 (6)	0.0113 (7)	0.0009 (7)
C5	0.0307 (8)	0.0245 (8)	0.0400 (9)	−0.0049 (6)	0.0120 (7)	0.0023 (7)
C11	0.0478 (11)	0.0397 (10)	0.0400 (10)	0.0014 (8)	0.0180 (8)	0.0000 (8)
C7	0.0462 (11)	0.0508 (12)	0.0397 (10)	0.0010 (9)	0.0154 (8)	0.0041 (9)
C4	0.0315 (9)	0.0413 (11)	0.0705 (14)	−0.0024 (8)	0.0178 (9)	0.0140 (10)
C6	0.0395 (10)	0.0303 (10)	0.0824 (16)	−0.0018 (8)	0.0175 (10)	0.0143 (10)
C9	0.0547 (14)	0.0729 (18)	0.0800 (18)	0.0285 (13)	0.0219 (13)	0.0116 (14)
C10	0.0622 (14)	0.0614 (15)	0.0669 (15)	0.0164 (12)	0.0364 (12)	0.0021 (12)
C8	0.0574 (14)	0.0753 (17)	0.0524 (13)	0.0182 (12)	0.0102 (11)	0.0181 (12)
O01	0.0687 (16)	0.0490 (14)	0.0683 (15)	0.000	0.0296 (13)	0.000

Cu1—O2	1.9894 (11)	C11—H11	0.9300
Cu1—O2i	1.9894 (11)	C7—C8	1.380 (3)
Cu1—N1	1.9920 (15)	C7—H7	0.9300
Cu1—N1i	1.9921 (15)	C4—H4A	0.9600
O2—C1	1.273 (2)	C4—H4B	0.9600
N1—C11	1.337 (2)	C4—H4C	0.9600
N1—C7	1.338 (3)	C6—H6A	0.9600
O1—C1	1.241 (2)	C6—H6B	0.9600
C1—C2	1.512 (2)	C6—H6C	0.9600
C2—C3	1.394 (2)	C9—C10	1.361 (4)
C2—C5	1.401 (2)	C9—C8	1.377 (4)
C3—C5ii	1.401 (2)	C9—H9	0.9300
C3—C4	1.512 (2)	C10—H10	0.9300
C5—C3ii	1.401 (2)	C8—H8	0.9300
C5—C6	1.508 (3)	O01—H1A	0.92 (3)
C11—C10	1.374 (3)
O2—Cu1—O2i	180.00 (6)	N1—C7—C8	121.7 (2)
O2—Cu1—N1	90.64 (5)	N1—C7—H7	119.1
O2i—Cu1—N1	89.36 (5)	C8—C7—H7	119.1
O2—Cu1—N1i	89.36 (5)	C3—C4—H4A	109.5
O2i—Cu1—N1i	90.65 (5)	C3—C4—H4B	109.5
N1—Cu1—N1i	180.0	H4A—C4—H4B	109.5
C1—O2—Cu1	102.52 (10)	C3—C4—H4C	109.5
C11—N1—C7	118.53 (17)	H4A—C4—H4C	109.5
C11—N1—Cu1	119.71 (13)	H4B—C4—H4C	109.5
C7—N1—Cu1	121.76 (13)	C5—C6—H6A	109.5
O1—C1—O2	122.84 (15)	C5—C6—H6B	109.5
O1—C1—C2	120.22 (15)	H6A—C6—H6B	109.5
O2—C1—C2	116.93 (14)	C5—C6—H6C	109.5
C3—C2—C5	122.37 (14)	H6A—C6—H6C	109.5
C3—C2—C1	119.25 (14)	H6B—C6—H6C	109.5
C5—C2—C1	118.37 (15)	C10—C9—C8	119.0 (2)
C2—C3—C5ii	118.98 (15)	C10—C9—H9	120.5
C2—C3—C4	120.19 (15)	C8—C9—H9	120.5
C5ii—C3—C4	120.80 (16)	C9—C10—C11	119.3 (2)
C2—C5—C3ii	118.64 (15)	C9—C10—H10	120.4
C2—C5—C6	120.10 (15)	C11—C10—H10	120.4
C3ii—C5—C6	121.25 (16)	C9—C8—C7	119.2 (2)
N1—C11—C10	122.3 (2)	C9—C8—H8	120.4
N1—C11—H11	118.9	C7—C8—H8	120.4
C10—C11—H11	118.9
O2i—Cu1—O2—C1	93.10 (11)	C1—C2—C3—C5ii	179.58 (16)
N1—Cu1—O2—C1	89.16 (11)	C5—C2—C3—C4	−178.05 (18)
N1i—Cu1—O2—C1	−90.84 (11)	C3—C2—C5—C3ii	−0.2 (3)
O2—Cu1—N1—C11	−129.39 (14)	C1—C2—C5—C3ii	−179.59 (16)
O2i—Cu1—N1—C11	50.61 (14)	C3—C2—C5—C6	−179.15 (18)
O2—Cu1—N1—C7	50.15 (15)	C1—C2—C5—C6	1.5 (3)
O2i—Cu1—N1—C7	−129.85 (15)	C7—N1—C11—C10	0.8 (3)
Cu1—O2—C1—O1	−0.1 (2)	Cu1—N1—C11—C10	−179.66 (18)
Cu1—O2—C1—C2	179.68 (12)	C11—N1—C7—C8	−0.5 (3)
O1—C1—C2—C3	−94.9 (2)	Cu1—N1—C7—C8	179.92 (18)
O2—C1—C2—C3	85.3 (2)	C8—C9—C10—C11	−0.5 (4)
O1—C1—C2—C5	84.5 (2)	N1—C11—C10—C9	−0.3 (4)
O2—C1—C2—C5	−95.3 (2)	C10—C9—C8—C7	0.7 (4)
C5—C2—C3—C5ii	0.2 (3)	N1—C7—C8—C9	−0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O01—H1A···O1	0.92 (3)	1.93 (3)	2.854 (2)	173 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O01—H1A⋯O1	0.92 (3)	1.93 (3)	2.854 (2)	173 (3)