Aqua-[1-(4-carb-oxy-phen-yl)-1H-imidazole-κN](pyridine-2,6-dicarboxyl-ato-κO,N,O)copper(II) monohydrate.

In the title complex, [Cu(C(7)H(3)NO(4))(C(10)H(8)N(2)O(2))(H(2)O)]·H(2)O, the Cu(II) ion is in a slightly distorted square-pyramidal geometry. Two carboxyl-ate O atoms and one pyridine N atom from a pyridine-2,6-dicarboxyl-ate ligand chelate the Cu(II) ion, forming two stable five-membered metalla rings. One imidazole N atom from a 1-(4-carb-oxy-phen-yl)imidazole ligand and one water mol-ecule complete the five-coordination. O-H⋯O hydrogen bonds involving the coordinated water mol-ecules and carboxyl-ate groups link the complex mol-ecules into chain-containing dinuclear macrocycles. O-H⋯O hydrogen bonds involving the uncoordinated water mol-ecules link the chains into a layer extending parallel to (10[Formula: see text]).

Related literature

For the design and synthesis of compounds with metal–organic supra­molecular architectures, see: Bradshaw et al. (2005 ▶); Tian et al. (2005 ▶); Wang et al. (2009 ▶). For the use of N-containing heterocyclic carboxyl­ate ligands in metal–organic supra­molecular architectures, see: Bentiss et al. (2004 ▶); Yang et al. (2008 ▶); Zeng et al. (2006 ▶). For related structures, see: Li et al. (2008 ▶).

Experimental

Crystal data

[Cu(C7H3NO4)(C10H8N2O2)(H2O)]·H2O

M = 452.87

Triclinic,

a = 8.1638 (5) Å

b = 8.2081 (5) Å

c = 13.1265 (18) Å

α = 84.353 (16)°

β = 85.789 (13)°

γ = 80.736 (14)°

V = 862.43 (15) Å3

Z = 2

Mo Kα radiation

μ = 1.32 mm−1

T = 293 K

0.34 × 0.20 × 0.15 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.662, T max = 0.826

6749 measured reflections

3920 independent reflections

3485 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.096

S = 1.06

3920 reflections

322 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.62 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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/S1600536811015522/hy2420sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015522/hy2420Isup2.hkl

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

[Cu(C7H3NO4)(C10H8N2O2)(H2O)]·H2O	Z = 2
Mr = 452.87	F(000) = 462
Triclinic, P1	Dx = 1.744 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1638 (5) Å	Cell parameters from 6749 reflections
b = 8.2081 (5) Å	θ = 2.9–27.5°
c = 13.1265 (18) Å	µ = 1.32 mm−1
α = 84.353 (16)°	T = 293 K
β = 85.789 (13)°	Block, blue
γ = 80.736 (14)°	0.34 × 0.20 × 0.15 mm
V = 862.43 (15) Å3

Bruker APEX CCD diffractometer	3920 independent reflections
Radiation source: fine-focus sealed tube	3485 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.662, Tmax = 0.826	k = −10→10
6749 measured reflections	l = −14→17

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0513P)2 + 0.3344P] where P = (Fo2 + 2Fc2)/3
3920 reflections	(Δ/σ)max = 0.001
322 parameters	Δρmax = 0.37 e Å−3
5 restraints	Δρmin = −0.62 e Å−3

	x	y	z	Uiso*/Ueq
Cu1	0.51191 (3)	0.77853 (3)	0.81495 (2)	0.02775 (11)
O1	−0.5172 (2)	0.7396 (3)	0.42103 (17)	0.0516 (5)
N1	0.3000 (2)	0.8750 (2)	0.75900 (14)	0.0286 (4)
C1	−0.3561 (3)	0.6898 (3)	0.40439 (19)	0.0347 (5)
H1	−0.575 (4)	0.708 (5)	0.381 (2)	0.076 (12)*
O2	−0.2974 (2)	0.6052 (3)	0.33628 (16)	0.0533 (5)
N2	0.0788 (2)	0.8924 (2)	0.67065 (13)	0.0245 (4)
C2	−0.2492 (3)	0.7482 (3)	0.47641 (17)	0.0283 (5)
O3	0.7305 (2)	0.3533 (2)	0.70285 (15)	0.0414 (4)
N3	0.7383 (2)	0.6954 (2)	0.84101 (14)	0.0244 (4)
C3	−0.0783 (3)	0.6968 (3)	0.46374 (18)	0.0312 (5)
H3	−0.036 (4)	0.627 (4)	0.408 (2)	0.046 (8)*
O4	0.5460 (2)	0.5751 (2)	0.73733 (14)	0.0376 (4)
C4	0.0295 (3)	0.7460 (3)	0.52654 (18)	0.0300 (5)
H4	0.135 (4)	0.714 (3)	0.515 (2)	0.038 (7)*
O5	0.7779 (2)	1.0466 (2)	0.96052 (14)	0.0392 (4)
C5	−0.0332 (3)	0.8478 (2)	0.60358 (16)	0.0237 (4)
O6	0.57541 (19)	0.97815 (19)	0.87486 (13)	0.0333 (4)
C6	−0.2030 (3)	0.9038 (3)	0.61558 (17)	0.0290 (4)
H6	−0.247 (3)	0.981 (3)	0.673 (2)	0.039 (7)*
C7	−0.3103 (3)	0.8539 (3)	0.55223 (18)	0.0305 (5)
H7	−0.418 (4)	0.888 (3)	0.562 (2)	0.036 (7)*
C8	0.2294 (3)	0.8052 (3)	0.69116 (17)	0.0282 (4)
H8	0.265 (3)	0.706 (3)	0.6699 (18)	0.026 (6)*
C9	0.1899 (3)	1.0144 (3)	0.78355 (18)	0.0290 (5)
H9	0.213 (3)	1.084 (3)	0.830 (2)	0.030 (6)*
C10	0.0526 (3)	1.0255 (3)	0.72996 (17)	0.0280 (4)
H10	−0.043 (3)	1.102 (3)	0.726 (2)	0.033 (7)*
C11	0.6874 (3)	0.4845 (3)	0.74368 (17)	0.0291 (5)
C12	0.8070 (3)	0.5506 (3)	0.80631 (17)	0.0255 (4)
C13	0.9705 (3)	0.4866 (3)	0.82600 (19)	0.0309 (5)
H13	1.023 (4)	0.383 (4)	0.803 (2)	0.052 (8)*
C14	1.0569 (3)	0.5759 (3)	0.88262 (19)	0.0324 (5)
H14	1.165 (4)	0.537 (4)	0.895 (2)	0.049 (8)*
C15	0.9826 (3)	0.7273 (3)	0.91638 (18)	0.0287 (4)
H15	1.038 (3)	0.791 (3)	0.955 (2)	0.037 (7)*
C16	0.8205 (3)	0.7846 (3)	0.89290 (16)	0.0240 (4)
C17	0.7182 (3)	0.9512 (3)	0.91352 (17)	0.0269 (4)
O1W	0.4032 (2)	0.6744 (2)	0.96552 (14)	0.0357 (4)
O2W	0.3880 (2)	1.2940 (2)	0.87970 (16)	0.0427 (4)
H1W1	0.474 (4)	0.658 (5)	1.008 (2)	0.074 (12)*
H2W1	0.349 (4)	0.756 (3)	0.990 (2)	0.055 (9)*
H1W2	0.445 (4)	1.203 (3)	0.869 (2)	0.054 (9)*
H2W2	0.396 (4)	1.341 (4)	0.8208 (17)	0.061 (11)*

	U11	U22	U33	U12	U13	U23
Cu1	0.02014 (15)	0.02746 (16)	0.03696 (18)	0.00146 (10)	−0.01098 (11)	−0.01095 (11)
O1	0.0321 (10)	0.0655 (13)	0.0633 (13)	0.0001 (9)	−0.0194 (9)	−0.0361 (11)
N1	0.0232 (9)	0.0299 (9)	0.0334 (10)	0.0004 (7)	−0.0105 (7)	−0.0080 (7)
C1	0.0339 (12)	0.0319 (12)	0.0404 (13)	−0.0037 (9)	−0.0120 (10)	−0.0084 (10)
O2	0.0403 (10)	0.0672 (13)	0.0592 (13)	−0.0047 (9)	−0.0134 (9)	−0.0379 (11)
N2	0.0224 (8)	0.0254 (9)	0.0266 (9)	−0.0013 (7)	−0.0083 (7)	−0.0049 (7)
C2	0.0292 (11)	0.0288 (11)	0.0283 (11)	−0.0037 (9)	−0.0113 (9)	−0.0029 (8)
O3	0.0322 (9)	0.0394 (9)	0.0561 (11)	0.0020 (7)	−0.0108 (8)	−0.0277 (8)
N3	0.0204 (8)	0.0244 (8)	0.0293 (9)	−0.0010 (7)	−0.0051 (7)	−0.0077 (7)
C3	0.0335 (12)	0.0317 (11)	0.0290 (11)	−0.0005 (9)	−0.0074 (9)	−0.0092 (9)
O4	0.0268 (8)	0.0371 (9)	0.0522 (10)	0.0015 (7)	−0.0155 (7)	−0.0211 (8)
C4	0.0224 (10)	0.0351 (12)	0.0325 (11)	0.0003 (9)	−0.0063 (9)	−0.0073 (9)
O5	0.0319 (9)	0.0365 (9)	0.0534 (11)	−0.0019 (7)	−0.0107 (8)	−0.0240 (8)
C5	0.0238 (10)	0.0247 (10)	0.0232 (10)	−0.0031 (8)	−0.0087 (8)	−0.0012 (8)
O6	0.0265 (8)	0.0262 (8)	0.0488 (10)	0.0031 (6)	−0.0151 (7)	−0.0131 (7)
C6	0.0258 (10)	0.0341 (11)	0.0273 (11)	0.0003 (9)	−0.0065 (8)	−0.0074 (9)
C7	0.0214 (10)	0.0391 (12)	0.0318 (11)	−0.0018 (9)	−0.0070 (9)	−0.0074 (9)
C8	0.0238 (10)	0.0287 (11)	0.0326 (11)	0.0021 (8)	−0.0104 (8)	−0.0084 (9)
C9	0.0278 (11)	0.0257 (10)	0.0340 (12)	0.0001 (8)	−0.0097 (9)	−0.0073 (9)
C10	0.0264 (11)	0.0259 (10)	0.0321 (11)	0.0006 (9)	−0.0083 (9)	−0.0075 (8)
C11	0.0248 (10)	0.0319 (11)	0.0327 (11)	−0.0037 (9)	−0.0055 (9)	−0.0120 (9)
C12	0.0224 (10)	0.0255 (10)	0.0294 (11)	−0.0021 (8)	−0.0038 (8)	−0.0077 (8)
C13	0.0244 (11)	0.0280 (11)	0.0397 (13)	0.0038 (9)	−0.0053 (9)	−0.0097 (9)
C14	0.0202 (10)	0.0355 (12)	0.0413 (13)	0.0017 (9)	−0.0085 (9)	−0.0071 (10)
C15	0.0250 (10)	0.0328 (11)	0.0303 (11)	−0.0055 (9)	−0.0074 (9)	−0.0068 (9)
C16	0.0216 (9)	0.0242 (10)	0.0272 (10)	−0.0030 (8)	−0.0050 (8)	−0.0060 (8)
C17	0.0229 (10)	0.0274 (10)	0.0314 (11)	−0.0019 (8)	−0.0043 (8)	−0.0085 (8)
O1W	0.0334 (9)	0.0336 (9)	0.0407 (10)	0.0007 (7)	−0.0077 (8)	−0.0119 (7)
O2W	0.0458 (11)	0.0343 (10)	0.0467 (11)	0.0060 (8)	−0.0110 (9)	−0.0103 (8)

Cu1—N1	1.9467 (18)	O5—C17	1.222 (3)
Cu1—N3	1.9076 (17)	C5—C6	1.391 (3)
Cu1—O4	2.0118 (16)	O6—C17	1.283 (3)
Cu1—O6	2.0393 (16)	C6—C7	1.385 (3)
Cu1—O1W	2.2537 (19)	C6—H6	1.04 (3)
O1—C1	1.322 (3)	C7—H7	0.88 (3)
O1—H1	0.81 (1)	C8—H8	0.89 (3)
N1—C8	1.318 (3)	C9—C10	1.353 (3)
N1—C9	1.386 (3)	C9—H9	0.92 (3)
C1—O2	1.210 (3)	C10—H10	0.92 (3)
C1—C2	1.493 (3)	C11—C12	1.517 (3)
N2—C8	1.350 (3)	C12—C13	1.386 (3)
N2—C10	1.383 (3)	C13—C14	1.392 (3)
N2—C5	1.426 (3)	C13—H13	0.95 (3)
C2—C3	1.393 (3)	C14—C15	1.391 (3)
C2—C7	1.396 (3)	C14—H14	0.91 (3)
O3—C11	1.239 (3)	C15—C16	1.378 (3)
N3—C16	1.332 (3)	C15—H15	0.95 (3)
N3—C12	1.337 (3)	C16—C17	1.521 (3)
C3—C4	1.379 (3)	O1W—H1W1	0.82 (2)
C3—H3	0.98 (3)	O1W—H2W1	0.82 (2)
O4—C11	1.272 (3)	O2W—H1W2	0.83 (2)
C4—C5	1.391 (3)	O2W—H2W2	0.83 (2)
C4—H4	0.87 (3)
N3—Cu1—N1	167.81 (8)	C5—C6—H6	119.4 (16)
N3—Cu1—O4	80.11 (7)	C6—C7—C2	120.5 (2)
N1—Cu1—O4	95.85 (7)	C6—C7—H7	118.2 (18)
N3—Cu1—O6	80.22 (7)	C2—C7—H7	121.3 (18)
N1—Cu1—O6	100.91 (7)	N1—C8—N2	110.75 (19)
O4—Cu1—O6	156.95 (7)	N1—C8—H8	125.3 (16)
N3—Cu1—O1W	96.05 (7)	N2—C8—H8	123.1 (16)
N1—Cu1—O1W	95.97 (8)	C10—C9—N1	109.0 (2)
O4—Cu1—O1W	99.71 (7)	C10—C9—H9	128.9 (16)
O6—Cu1—O1W	94.19 (7)	N1—C9—H9	122.2 (16)
C1—O1—H1	114 (3)	C9—C10—N2	106.46 (19)
C8—N1—C9	106.55 (18)	C9—C10—H10	132.6 (17)
C8—N1—Cu1	123.09 (15)	N2—C10—H10	120.9 (17)
C9—N1—Cu1	130.21 (15)	O3—C11—O4	125.2 (2)
O2—C1—O1	123.7 (2)	O3—C11—C12	120.44 (19)
O2—C1—C2	121.8 (2)	O4—C11—C12	114.40 (18)
O1—C1—C2	114.5 (2)	N3—C12—C13	119.5 (2)
C8—N2—C10	107.26 (18)	N3—C12—C11	111.02 (18)
C8—N2—C5	125.26 (18)	C13—C12—C11	129.41 (19)
C10—N2—C5	127.41 (18)	C12—C13—C14	118.2 (2)
C3—C2—C7	119.1 (2)	C12—C13—H13	122 (2)
C3—C2—C1	117.1 (2)	C14—C13—H13	119.8 (19)
C7—C2—C1	123.8 (2)	C15—C14—C13	120.9 (2)
C16—N3—C12	123.10 (18)	C15—C14—H14	119.7 (19)
C16—N3—Cu1	118.33 (14)	C13—C14—H14	119.3 (19)
C12—N3—Cu1	118.58 (15)	C16—C15—C14	117.7 (2)
C4—C3—C2	120.8 (2)	C16—C15—H15	119.2 (17)
C4—C3—H3	120.8 (18)	C14—C15—H15	123.0 (17)
C2—C3—H3	118.4 (18)	N3—C16—C15	120.51 (19)
C11—O4—Cu1	115.70 (14)	N3—C16—C17	111.96 (18)
C3—C4—C5	119.6 (2)	C15—C16—C17	127.41 (19)
C3—C4—H4	117.9 (19)	O5—C17—O6	126.6 (2)
C5—C4—H4	122.4 (19)	O5—C17—C16	119.27 (19)
C6—C5—C4	120.4 (2)	O6—C17—C16	114.11 (18)
C6—C5—N2	120.54 (18)	Cu1—O1W—H1W1	110 (3)
C4—C5—N2	119.10 (19)	Cu1—O1W—H2W1	104 (2)
C17—O6—Cu1	114.41 (13)	H1W1—O1W—H2W1	96 (3)
C7—C6—C5	119.6 (2)	H1W2—O2W—H2W2	98 (3)
C7—C6—H6	121.0 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3i	0.81 (1)	1.90 (1)	2.710 (2)	173 (4)
O1W—H1W1···O2Wii	0.82 (2)	2.02 (2)	2.803 (3)	159 (4)
O1W—H2W1···O5ii	0.82 (2)	1.92 (2)	2.740 (2)	177 (3)
O2W—H1W2···O6	0.83 (2)	1.98 (2)	2.794 (2)	168 (3)
O2W—H2W2···O2iii	0.83 (2)	2.25 (2)	2.986 (3)	148 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3i	0.81 (1)	1.90 (1)	2.710 (2)	173 (4)
O1W—H1W1⋯O2Wii	0.82 (2)	2.02 (2)	2.803 (3)	159 (4)
O1W—H2W1⋯O5ii	0.82 (2)	1.92 (2)	2.740 (2)	177 (3)
O2W—H1W2⋯O6	0.83 (2)	1.98 (2)	2.794 (2)	168 (3)
O2W—H2W2⋯O2iii	0.83 (2)	2.25 (2)	2.986 (3)	148 (3)

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