Aqua-(6,6'-oxydipicolinato-κO,N,N',O')copper(II).

In the title complex, [Cu(C(12)H(6)N(2)O(5))(H(2)O)], the Cu(II) ion is in a slightly distorted square-pyramidal coordination environment with two N and two O atoms from a 6,6'-oxydipicolinate ligand occupying the basal plane and a water ligand in the apical site. The dihedral angle between the two pyridine rings is 5.51 (6)°. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link mol-ecules into a two-dimensional network. In addition, weak inter-molecular C-H⋯O and C=O(lone pair)⋯π(ring) inter-actions, with O⋯ring-centroid distances of 3.697 (4) and 3.094 (4) Å, provide additional stabilization.

Related literature

For inter­molecular inter­actions, see: Choudhury et al. (2008 ▶). For the applications of picolinic acid compounds, see: Mann et al. (1992 ▶).

Experimental

Crystal data

[Cu(C12H6N2O5)(H2O)]

M = 339.74

Monoclinic,

a = 7.2487 (16) Å

b = 21.055 (4) Å

c = 8.2269 (17) Å

β = 110.201 (9)°

V = 1178.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.89 mm−1

T = 296 K

0.40 × 0.35 × 0.30 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.519, T max = 0.602

6790 measured reflections

2074 independent reflections

1806 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.110

S = 1.18

2074 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.37 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680905346X/lh2964sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905346X/lh2964Isup2.hkl

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

[Cu(C12H6N2O5)(H2O)]	F(000) = 684
Mr = 339.74	Dx = 1.915 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2501 reflections
a = 7.2487 (16) Å	θ = 2.8–27.5°
b = 21.055 (4) Å	µ = 1.89 mm−1
c = 8.2269 (17) Å	T = 296 K
β = 110.201 (9)°	Block, blue
V = 1178.4 (4) Å3	0.40 × 0.35 × 0.30 mm
Z = 4

Siemens SMART CCD diffractometer	2074 independent reflections
Radiation source: fine-focus sealed tube	1806 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.519, Tmax = 0.602	k = −24→24
6790 measured reflections	l = −9→8

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.18	w = 1/[σ2(Fo2) + (0.0671P)2 + 0.1209P] where P = (Fo2 + 2Fc2)/3
2074 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.33165 (5)	0.109980 (17)	0.96148 (4)	0.02725 (18)
O3	0.2907 (3)	0.05841 (10)	1.1417 (3)	0.0327 (5)
N2	0.4163 (4)	0.14875 (12)	0.7848 (3)	0.0265 (6)
O1	0.4318 (3)	0.18774 (11)	1.0899 (3)	0.0336 (5)
O5	0.3272 (4)	0.06644 (11)	0.5777 (3)	0.0368 (6)
N1	0.2837 (4)	0.03042 (12)	0.8315 (3)	0.0254 (6)
O4	0.2158 (4)	−0.04040 (11)	1.1935 (3)	0.0409 (6)
O2	0.5275 (4)	0.28511 (11)	1.0481 (3)	0.0410 (6)
C12	0.2463 (4)	0.00062 (15)	1.1003 (4)	0.0268 (7)
C1	0.4833 (5)	0.23022 (15)	1.0031 (4)	0.0297 (7)
O6	0.0171 (3)	0.14739 (11)	0.8390 (3)	0.0382 (6)
H6A	−0.0120	0.1623	0.7373	0.046*
H6B	−0.0521	0.1144	0.8010	0.046*
C2	0.4850 (5)	0.20891 (14)	0.8261 (4)	0.0284 (7)
C5	0.4587 (5)	0.15934 (17)	0.5117 (4)	0.0342 (8)
H5	0.4473	0.1419	0.4048	0.041*
C11	0.2346 (4)	−0.01770 (15)	0.9187 (4)	0.0258 (7)
C10	0.1814 (5)	−0.07640 (16)	0.8462 (4)	0.0348 (8)
H10	0.1481	−0.1089	0.9075	0.042*
C6	0.4036 (5)	0.12555 (15)	0.6311 (4)	0.0298 (7)
C8	0.2272 (5)	−0.03744 (16)	0.5894 (4)	0.0358 (8)
H8	0.2241	−0.0430	0.4763	0.043*
C7	0.2808 (5)	0.02011 (15)	0.6721 (4)	0.0280 (7)
C9	0.1787 (5)	−0.08608 (16)	0.6763 (4)	0.0374 (8)
H9	0.1441	−0.1255	0.6235	0.045*
C3	0.5440 (5)	0.24521 (16)	0.7162 (4)	0.0366 (8)
H3	0.5919	0.2861	0.7470	0.044*
C4	0.5311 (5)	0.21967 (17)	0.5561 (5)	0.0407 (9)
H4	0.5715	0.2435	0.4793	0.049*

	U11	U22	U33	U12	U13	U23
Cu1	0.0409 (3)	0.0226 (3)	0.0216 (3)	−0.00293 (15)	0.01511 (19)	−0.00212 (14)
O3	0.0481 (14)	0.0300 (13)	0.0229 (11)	−0.0044 (10)	0.0161 (10)	−0.0017 (9)
N2	0.0309 (14)	0.0253 (14)	0.0242 (13)	0.0005 (11)	0.0105 (10)	0.0002 (11)
O1	0.0470 (14)	0.0288 (12)	0.0267 (11)	−0.0051 (10)	0.0150 (10)	−0.0053 (9)
O5	0.0589 (16)	0.0326 (13)	0.0237 (11)	−0.0090 (11)	0.0203 (11)	−0.0052 (10)
N1	0.0327 (14)	0.0225 (13)	0.0220 (12)	−0.0009 (11)	0.0108 (10)	−0.0010 (10)
O4	0.0594 (16)	0.0381 (14)	0.0303 (12)	−0.0093 (12)	0.0219 (11)	0.0034 (11)
O2	0.0495 (15)	0.0263 (13)	0.0471 (15)	−0.0071 (10)	0.0166 (12)	−0.0104 (11)
C12	0.0283 (16)	0.0302 (18)	0.0215 (15)	0.0000 (13)	0.0082 (13)	0.0033 (13)
C1	0.0275 (16)	0.0285 (19)	0.0323 (16)	0.0031 (13)	0.0094 (13)	−0.0018 (14)
O6	0.0378 (13)	0.0339 (13)	0.0400 (13)	0.0015 (10)	0.0098 (11)	0.0019 (11)
C2	0.0286 (16)	0.0233 (16)	0.0310 (16)	−0.0001 (13)	0.0075 (13)	0.0014 (13)
C5	0.0361 (18)	0.040 (2)	0.0298 (17)	0.0017 (14)	0.0164 (14)	0.0037 (14)
C11	0.0289 (16)	0.0250 (16)	0.0234 (15)	0.0026 (12)	0.0087 (12)	0.0014 (12)
C10	0.048 (2)	0.0268 (18)	0.0324 (18)	−0.0054 (14)	0.0167 (15)	−0.0001 (14)
C6	0.0361 (18)	0.0305 (18)	0.0246 (16)	0.0025 (14)	0.0130 (13)	0.0022 (13)
C8	0.046 (2)	0.036 (2)	0.0277 (16)	−0.0008 (15)	0.0161 (15)	−0.0095 (15)
C7	0.0348 (17)	0.0279 (17)	0.0227 (15)	0.0012 (13)	0.0117 (13)	−0.0001 (13)
C9	0.050 (2)	0.0285 (18)	0.0346 (18)	−0.0074 (16)	0.0160 (16)	−0.0114 (15)
C3	0.0374 (19)	0.0310 (18)	0.042 (2)	−0.0050 (15)	0.0142 (15)	0.0034 (16)
C4	0.043 (2)	0.042 (2)	0.042 (2)	−0.0028 (16)	0.0217 (16)	0.0123 (17)

Cu1—O3	1.942 (2)	O6—H6A	0.8500
Cu1—N2	1.942 (3)	O6—H6B	0.8501
Cu1—O1	1.948 (2)	C2—C3	1.361 (5)
Cu1—N1	1.953 (2)	C5—C4	1.375 (5)
Cu1—O6	2.290 (2)	C5—C6	1.379 (4)
O3—C12	1.275 (4)	C5—H5	0.9300
N2—C6	1.328 (4)	C11—C10	1.368 (5)
N2—C2	1.361 (4)	C10—C9	1.406 (5)
O1—C1	1.278 (4)	C10—H10	0.9300
O5—C7	1.359 (4)	C8—C9	1.363 (5)
O5—C6	1.371 (4)	C8—C7	1.378 (5)
N1—C7	1.323 (4)	C8—H8	0.9300
N1—C11	1.358 (4)	C9—H9	0.9300
O4—C12	1.225 (4)	C3—C4	1.395 (5)
O2—C1	1.222 (4)	C3—H3	0.9300
C12—C11	1.517 (4)	C4—H4	0.9300
C1—C2	1.528 (4)
O3—Cu1—N2	167.91 (10)	N2—C2—C1	112.9 (3)
O3—Cu1—O1	100.51 (9)	C3—C2—C1	125.2 (3)
N2—Cu1—O1	84.13 (10)	C4—C5—C6	117.7 (3)
O3—Cu1—N1	83.87 (9)	C4—C5—H5	121.1
N2—Cu1—N1	89.62 (10)	C6—C5—H5	121.1
O1—Cu1—N1	168.68 (10)	N1—C11—C10	122.0 (3)
O3—Cu1—O6	97.86 (10)	N1—C11—C12	113.2 (3)
N2—Cu1—O6	92.86 (10)	C10—C11—C12	124.8 (3)
O1—Cu1—O6	94.45 (9)	C11—C10—C9	118.0 (3)
N1—Cu1—O6	95.29 (10)	C11—C10—H10	121.0
C12—O3—Cu1	114.87 (19)	C9—C10—H10	121.0
C6—N2—C2	118.7 (3)	N2—C6—O5	121.8 (3)
C6—N2—Cu1	128.4 (2)	N2—C6—C5	123.1 (3)
C2—N2—Cu1	112.8 (2)	O5—C6—C5	115.1 (3)
C1—O1—Cu1	114.29 (19)	C9—C8—C7	118.8 (3)
C7—O5—C6	128.3 (2)	C9—C8—H8	120.6
C7—N1—C11	118.9 (3)	C7—C8—H8	120.6
C7—N1—Cu1	128.5 (2)	N1—C7—O5	121.8 (3)
C11—N1—Cu1	112.4 (2)	N1—C7—C8	122.6 (3)
O4—C12—O3	126.1 (3)	O5—C7—C8	115.6 (3)
O4—C12—C11	118.5 (3)	C8—C9—C10	119.7 (3)
O3—C12—C11	115.4 (3)	C8—C9—H9	120.2
O2—C1—O1	126.1 (3)	C10—C9—H9	120.2
O2—C1—C2	118.6 (3)	C2—C3—C4	118.5 (3)
O1—C1—C2	115.3 (3)	C2—C3—H3	120.8
Cu1—O6—H6A	115.6	C4—C3—H3	120.8
Cu1—O6—H6B	104.6	C5—C4—C3	120.1 (3)
H6A—O6—H6B	91.5	C5—C4—H4	119.9
N2—C2—C3	121.9 (3)	C3—C4—H4	119.9

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O4i	0.93	2.31	3.229 (4)	171
C9—H9···O2ii	0.93	2.42	3.331 (4)	165
C4—H4···O6iii	0.93	2.54	3.303 (4)	140
O6—H6B···O4iv	0.85	1.97	2.772 (3)	157
O6—H6A···O2v	0.85	2.01	2.807 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O4i	0.93	2.31	3.229 (4)	171
C9—H9⋯O2ii	0.93	2.42	3.331 (4)	165
C4—H4⋯O6iii	0.93	2.54	3.303 (4)	140
O6—H6B⋯O4iv	0.85	1.97	2.772 (3)	157
O6—H6A⋯O2v	0.85	2.01	2.807 (3)	156

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