trans-Bis(5-carb-oxy-2-methyl-1H-imidazole-4-carboxyl-ato-κN,O)copper(II).

In the title compound, [Cu(C(6)H(5)N(2)O(4))(2)], the copper(II) atom lies on an inversion centre and is in an N(2)O(2) four-coordinate environment with a nearly regular square-planar geometry. An extended network of intra-molecular O-H⋯O and inter-molecular N-H⋯O and C-H⋯O hydrogen bonds stabil-izes the crystal structure.

Related literature

For the synthesis and crystal structure of metal complexes with N-heterocyclic carboxylic acids, see: Nie et al. (2007 ▶); Liang et al. (2002 ▶); Net et al. (1989 ▶); Zeng et al. (2008 ▶).

Experimental

Crystal data

[Cu(C6H5N2O4)2]

M = 401.78

Monoclinic,

a = 7.3780 (17) Å

b = 7.575 (2) Å

c = 12.863 (3) Å

β = 101.287 (13)°

V = 705.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.61 mm−1

T = 292 K

0.30 × 0.25 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.638, T max = 0.727

5198 measured reflections

1609 independent reflections

1472 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.084

S = 1.07

1609 reflections

116 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.66 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536809016791/rz2318sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016791/rz2318Isup2.hkl

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

[Cu(C6H5N2O4)2]	F(000) = 406
Mr = 401.78	Dx = 1.893 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2111 reflections
a = 7.3780 (17) Å	θ = 3.1–27.5°
b = 7.575 (2) Å	µ = 1.61 mm−1
c = 12.863 (3) Å	T = 292 K
β = 101.287 (13)°	Prism, blue
V = 705.0 (3) Å3	0.30 × 0.25 × 0.20 mm
Z = 2

Rigaku SCXmini diffractometer	1609 independent reflections
Radiation source: fine-focus sealed tube	1472 reflections with I > 2σ(I)
graphite	Rint = 0.019
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→8
Tmin = 0.638, Tmax = 0.727	l = −16→16
5198 measured 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0506P)2 + 0.3299P] where P = (Fo2 + 2Fc2)/3
1609 reflections	(Δ/σ)max < 0.001
116 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.66 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	0.5000	0.0000	0.02591 (14)
C1	0.3363 (3)	0.5580 (3)	0.26068 (15)	0.0322 (4)
H1A	0.4201	0.6562	0.2725	0.048*
H1B	0.3575	0.4828	0.3219	0.048*
H1C	0.2114	0.6005	0.2482	0.048*
C2	0.3672 (2)	0.4571 (3)	0.16737 (14)	0.0222 (4)
C3	0.3316 (2)	0.3269 (2)	0.01393 (13)	0.0211 (3)
C4	0.5089 (2)	0.2949 (2)	0.06414 (13)	0.0221 (4)
C5	0.6677 (3)	0.2144 (3)	0.02784 (15)	0.0267 (4)
C6	0.2221 (2)	0.2795 (3)	−0.09127 (14)	0.0241 (4)
N1	0.24525 (19)	0.4288 (2)	0.07763 (11)	0.0216 (3)
N2	0.5278 (2)	0.3781 (2)	0.16036 (11)	0.0226 (3)
H2A	0.6266	0.3796	0.2086	0.027*
O1	0.06229 (18)	0.3460 (2)	−0.11265 (10)	0.0328 (3)
O2	0.29058 (19)	0.1816 (2)	−0.15194 (10)	0.0325 (3)
O3	0.6306 (2)	0.1289 (2)	−0.06309 (11)	0.0362 (4)
H3A	0.5102	0.1358	−0.0972	0.054*
O4	0.8232 (2)	0.2331 (2)	0.07777 (12)	0.0396 (4)

	U11	U22	U33	U12	U13	U23
Cu1	0.01512 (18)	0.0374 (2)	0.02196 (19)	0.00490 (12)	−0.00433 (12)	−0.00595 (12)
C1	0.0263 (10)	0.0449 (12)	0.0231 (9)	0.0015 (9)	−0.0008 (7)	−0.0072 (8)
C2	0.0190 (8)	0.0268 (9)	0.0190 (8)	−0.0015 (7)	−0.0004 (6)	0.0029 (7)
C3	0.0172 (8)	0.0242 (9)	0.0205 (8)	−0.0010 (6)	0.0000 (6)	0.0001 (6)
C4	0.0189 (8)	0.0240 (9)	0.0217 (8)	0.0008 (7)	−0.0001 (6)	0.0029 (7)
C5	0.0210 (8)	0.0291 (10)	0.0294 (9)	0.0036 (7)	0.0034 (7)	0.0054 (7)
C6	0.0201 (8)	0.0304 (10)	0.0196 (8)	−0.0010 (7)	−0.0013 (6)	−0.0023 (7)
N1	0.0165 (7)	0.0275 (8)	0.0190 (7)	0.0003 (6)	−0.0013 (5)	−0.0017 (6)
N2	0.0172 (7)	0.0294 (8)	0.0184 (7)	0.0003 (6)	−0.0038 (5)	0.0025 (6)
O1	0.0206 (7)	0.0470 (9)	0.0263 (7)	0.0062 (6)	−0.0065 (5)	−0.0103 (6)
O2	0.0252 (7)	0.0441 (8)	0.0256 (7)	0.0036 (6)	−0.0010 (5)	−0.0113 (6)
O3	0.0273 (7)	0.0465 (9)	0.0342 (8)	0.0079 (6)	0.0047 (6)	−0.0077 (6)
O4	0.0196 (7)	0.0569 (10)	0.0390 (8)	0.0073 (7)	−0.0025 (6)	0.0007 (7)

Cu1—N1	1.9633 (15)	C3—N1	1.370 (2)
Cu1—N1i	1.9633 (15)	C3—C6	1.478 (2)
Cu1—O1	1.9830 (14)	C4—N2	1.372 (2)
Cu1—O1i	1.9830 (14)	C4—C5	1.475 (3)
C1—C2	1.478 (3)	C5—O4	1.208 (2)
C1—H1A	0.9600	C5—O3	1.318 (2)
C1—H1B	0.9600	C6—O2	1.252 (2)
C1—H1C	0.9600	C6—O1	1.262 (2)
C2—N1	1.335 (2)	N2—H2A	0.8600
C2—N2	1.346 (2)	O3—H3A	0.9117
C3—C4	1.363 (2)
N1—Cu1—N1i	180.0	C3—C4—N2	105.31 (15)
N1—Cu1—O1	83.56 (6)	C3—C4—C5	132.21 (17)
N1i—Cu1—O1	96.44 (6)	N2—C4—C5	121.95 (16)
N1—Cu1—O1i	96.44 (6)	O4—C5—O3	122.69 (18)
N1i—Cu1—O1i	83.56 (6)	O4—C5—C4	120.88 (18)
O1—Cu1—O1i	180.00 (5)	O3—C5—C4	116.37 (16)
C2—C1—H1A	109.5	O2—C6—O1	125.06 (16)
C2—C1—H1B	109.5	O2—C6—C3	119.96 (16)
H1A—C1—H1B	109.5	O1—C6—C3	114.98 (16)
C2—C1—H1C	109.5	C2—N1—C3	107.11 (14)
H1A—C1—H1C	109.5	C2—N1—Cu1	142.56 (13)
H1B—C1—H1C	109.5	C3—N1—Cu1	109.91 (11)
N1—C2—N2	108.89 (16)	C2—N2—C4	109.26 (14)
N1—C2—C1	126.93 (17)	C2—N2—H2A	125.4
N2—C2—C1	124.18 (16)	C4—N2—H2A	125.4
C4—C3—N1	109.42 (15)	C6—O1—Cu1	114.58 (11)
C4—C3—C6	133.84 (17)	C5—O3—H3A	114.3
N1—C3—C6	116.72 (15)
N1—C3—C4—N2	0.6 (2)	C4—C3—N1—C2	−1.1 (2)
C6—C3—C4—N2	178.80 (19)	C6—C3—N1—C2	−179.58 (16)
N1—C3—C4—C5	−170.85 (19)	C4—C3—N1—Cu1	173.21 (12)
C6—C3—C4—C5	7.3 (4)	C6—C3—N1—Cu1	−5.3 (2)
C3—C4—C5—O4	163.5 (2)	O1—Cu1—N1—C2	175.3 (2)
N2—C4—C5—O4	−6.8 (3)	O1i—Cu1—N1—C2	−4.7 (2)
C3—C4—C5—O3	−13.6 (3)	O1—Cu1—N1—C3	4.36 (12)
N2—C4—C5—O3	176.04 (17)	O1i—Cu1—N1—C3	−175.64 (12)
C4—C3—C6—O2	4.4 (3)	N1—C2—N2—C4	−0.7 (2)
N1—C3—C6—O2	−177.58 (17)	C1—C2—N2—C4	179.41 (18)
C4—C3—C6—O1	−174.8 (2)	C3—C4—N2—C2	0.0 (2)
N1—C3—C6—O1	3.2 (3)	C5—C4—N2—C2	172.59 (17)
N2—C2—N1—C3	1.1 (2)	O2—C6—O1—Cu1	−178.45 (16)
C1—C2—N1—C3	−179.04 (19)	C3—C6—O1—Cu1	0.7 (2)
N2—C2—N1—Cu1	−170.06 (15)	N1—Cu1—O1—C6	−2.89 (14)
C1—C2—N1—Cu1	9.8 (4)	N1i—Cu1—O1—C6	177.11 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ii	0.86	2.01	2.822 (2)	157
C1—H1A···O4iii	0.96	2.49	3.217 (2)	132
C1—H1B···O3iv	0.96	2.58	3.285 (3)	130
C1—H1C···O1i	0.96	2.43	3.258 (3)	144
O3—H3A···O2	0.91	1.67	2.576 (2)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2i	0.86	2.01	2.822 (2)	157
C1—H1A⋯O4ii	0.96	2.49	3.217 (2)	132
C1—H1B⋯O3iii	0.96	2.58	3.285 (3)	130
C1—H1C⋯O1iv	0.96	2.43	3.258 (3)	144
O3—H3A⋯O2	0.91	1.67	2.576 (2)	171

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