Diaqua-bis-(4-carb-oxy-2-propyl-1H-imidazole-5-carboxyl-ato-κN,O)copper(II) N,N-dimethyl-formamide disolvate.

In the title complex, [Cu(C(8)H(9)N(2)O(4))(2)(H(2)O)(2)]·2C(3)H(7)NO, the Cu(II) ion, lying on an inversion center, is six-coordinated in a slightly distorted octa-hedral geometry. Two N atoms and two O atoms from two H(2)pimda (H(3)pimda is 2-propyl-1H-4,5-dicarb-oxy-lic acid) ligands are in the equatorial plane. The axial positions are occupied by two O atoms from two water mol-ecules. A two-dimensional supra-molecular network parallel to (001) is constructed by N-H⋯O and O-H⋯O hydrogen bonds. An intra-molecular O-H⋯O hydrogen bond is also observed.

Related literature

For the potential uses and diverse structural types of metal complexes with imidazole-4,5-dicarb­oxy­lic acid, see: Li et al. (2006 ▶); Liu et al. (2004 ▶); Sun et al. (2005 ▶); Zou et al. (2006 ▶).

Experimental

Crystal data

[Cu(C8H9N2O4)2(H2O)2]·2C3H7NO

M = 640.11

Triclinic,

a = 7.2831 (8) Å

b = 9.250 (1) Å

c = 11.3329 (13) Å

α = 75.264 (1)°

β = 87.305 (2)°

γ = 68.416 (1)°

V = 685.68 (13) Å3

Z = 1

Mo Kα radiation

μ = 0.87 mm−1

T = 298 K

0.32 × 0.21 × 0.19 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.768, T max = 0.852

3603 measured reflections

2385 independent reflections

2011 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.097

S = 1.06

2385 reflections

187 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.29 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/S1600536810025249/hy2320sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025249/hy2320Isup2.hkl

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

[Cu(C8H9N2O4)2(H2O)2]·2C3H7NO	Z = 1
Mr = 640.11	F(000) = 335
Triclinic, P1	Dx = 1.550 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2831 (8) Å	Cell parameters from 1702 reflections
b = 9.250 (1) Å	θ = 2.5–25.9°
c = 11.3329 (13) Å	µ = 0.87 mm−1
α = 75.264 (1)°	T = 298 K
β = 87.305 (2)°	Cubic, blue
γ = 68.416 (1)°	0.32 × 0.21 × 0.19 mm
V = 685.68 (13) Å3

Bruker SMART 1000 CCD diffractometer	2385 independent reflections
Radiation source: fine-focus sealed tube	2011 reflections with I > 2σ(I)
graphite	Rint = 0.017
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→7
Tmin = 0.768, Tmax = 0.852	k = −10→10
3603 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0414P)2 + 0.548P] where P = (Fo2 + 2Fc2)/3
2385 reflections	(Δ/σ)max < 0.001
187 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

	x	y	z	Uiso*/Ueq
Cu1	0.5000	0.5000	0.5000	0.02632 (17)
N1	0.6271 (3)	0.2621 (3)	0.5343 (2)	0.0251 (5)
N2	0.7981 (3)	0.0045 (3)	0.5992 (2)	0.0295 (6)
H2	0.8707	−0.0862	0.6461	0.035*
N3	0.1268 (4)	0.4896 (3)	0.8656 (3)	0.0434 (7)
O1	0.4276 (3)	0.4348 (2)	0.31460 (19)	0.0387 (5)
O2	0.4952 (3)	0.2191 (3)	0.24467 (19)	0.0422 (6)
H2A	0.5573	0.1221	0.2687	0.063*
O3	0.6933 (4)	−0.0740 (3)	0.3193 (2)	0.0442 (6)
O4	0.8653 (3)	−0.2477 (2)	0.4863 (2)	0.0398 (5)
O5	0.2402 (3)	0.4858 (2)	0.56026 (19)	0.0353 (5)
H5A	0.2186	0.4061	0.5485	0.042*
H5B	0.1412	0.5701	0.5293	0.042*
O6	0.0414 (4)	0.7502 (3)	0.7641 (2)	0.0568 (7)
C1	0.5080 (4)	0.2896 (3)	0.3284 (3)	0.0305 (7)
C2	0.6222 (4)	0.1888 (3)	0.4434 (3)	0.0255 (6)
C3	0.7286 (4)	0.0262 (3)	0.4834 (3)	0.0265 (6)
C4	0.7665 (4)	−0.1092 (3)	0.4254 (3)	0.0305 (7)
C5	0.7356 (4)	0.1463 (3)	0.6284 (3)	0.0289 (7)
C6	0.7787 (5)	0.1646 (4)	0.7491 (3)	0.0414 (8)
H6A	0.7328	0.2782	0.7460	0.050*
H6B	0.9208	0.1199	0.7659	0.050*
C7	0.6827 (7)	0.0825 (6)	0.8528 (4)	0.0694 (12)
H7A	0.5414	0.1240	0.8336	0.083*
H7B	0.7328	−0.0316	0.8573	0.083*
C8	0.7160 (7)	0.1037 (5)	0.9754 (3)	0.0659 (12)
H8A	0.8439	0.0288	1.0098	0.099*
H8B	0.6159	0.0845	1.0282	0.099*
H8C	0.7097	0.2114	0.9668	0.099*
C9	0.0181 (5)	0.6215 (4)	0.7857 (3)	0.0451 (8)
H9	−0.0840	0.6167	0.7424	0.054*
C10	0.0974 (8)	0.3399 (5)	0.8779 (4)	0.0779 (14)
H10A	−0.0212	0.3605	0.8322	0.117*
H10B	0.0856	0.2932	0.9625	0.117*
H10C	0.2082	0.2669	0.8471	0.117*
C11	0.2925 (6)	0.4885 (5)	0.9321 (4)	0.0625 (11)
H11A	0.4116	0.4480	0.8910	0.094*
H11B	0.3049	0.4207	1.0134	0.094*
H11C	0.2709	0.5959	0.9361	0.094*

	U11	U22	U33	U12	U13	U23
Cu1	0.0281 (3)	0.0167 (3)	0.0329 (3)	−0.0064 (2)	−0.0004 (2)	−0.0065 (2)
N1	0.0284 (13)	0.0187 (11)	0.0282 (13)	−0.0084 (10)	0.0010 (10)	−0.0066 (10)
N2	0.0300 (14)	0.0166 (11)	0.0365 (14)	−0.0047 (10)	−0.0039 (11)	−0.0025 (10)
N3	0.0490 (18)	0.0311 (14)	0.0453 (17)	−0.0112 (13)	−0.0017 (13)	−0.0060 (12)
O1	0.0464 (14)	0.0227 (11)	0.0391 (13)	−0.0053 (10)	−0.0048 (10)	−0.0045 (9)
O2	0.0540 (15)	0.0332 (12)	0.0363 (13)	−0.0100 (11)	−0.0097 (10)	−0.0105 (10)
O3	0.0579 (16)	0.0319 (12)	0.0443 (14)	−0.0110 (11)	−0.0031 (12)	−0.0194 (10)
O4	0.0397 (13)	0.0185 (11)	0.0580 (15)	−0.0045 (9)	−0.0025 (11)	−0.0125 (10)
O5	0.0289 (11)	0.0218 (10)	0.0565 (14)	−0.0094 (9)	0.0037 (10)	−0.0123 (9)
O6	0.0589 (17)	0.0316 (13)	0.0649 (17)	−0.0080 (12)	−0.0174 (13)	0.0038 (12)
C1	0.0282 (16)	0.0297 (16)	0.0334 (17)	−0.0103 (13)	0.0012 (13)	−0.0082 (13)
C2	0.0263 (15)	0.0228 (14)	0.0309 (16)	−0.0122 (12)	0.0038 (12)	−0.0086 (12)
C3	0.0237 (15)	0.0227 (14)	0.0340 (17)	−0.0091 (12)	0.0046 (12)	−0.0083 (12)
C4	0.0256 (16)	0.0236 (15)	0.0445 (19)	−0.0096 (13)	0.0060 (13)	−0.0128 (14)
C5	0.0304 (16)	0.0222 (14)	0.0340 (17)	−0.0100 (12)	−0.0013 (13)	−0.0060 (12)
C6	0.053 (2)	0.0267 (16)	0.0416 (19)	−0.0119 (15)	−0.0131 (16)	−0.0051 (14)
C7	0.085 (3)	0.094 (3)	0.052 (3)	−0.050 (3)	0.019 (2)	−0.035 (2)
C8	0.079 (3)	0.067 (3)	0.051 (2)	−0.024 (2)	0.006 (2)	−0.018 (2)
C9	0.0362 (19)	0.047 (2)	0.048 (2)	−0.0092 (16)	−0.0039 (16)	−0.0138 (17)
C10	0.105 (4)	0.041 (2)	0.094 (3)	−0.033 (2)	0.015 (3)	−0.019 (2)
C11	0.050 (2)	0.058 (2)	0.062 (3)	−0.0083 (19)	−0.0161 (19)	0.001 (2)

Cu1—N1i	1.987 (2)	C1—C2	1.475 (4)
Cu1—N1	1.987 (2)	C2—C3	1.377 (4)
Cu1—O5i	2.020 (2)	C3—C4	1.491 (4)
Cu1—O5	2.020 (2)	C5—C6	1.481 (4)
Cu1—O1	2.458 (2)	C6—C7	1.519 (5)
N1—C5	1.336 (3)	C6—H6A	0.9700
N1—C2	1.378 (3)	C6—H6B	0.9700
N2—C5	1.344 (3)	C7—C8	1.494 (5)
N2—C3	1.368 (4)	C7—H7A	0.9700
N2—H2	0.8600	C7—H7B	0.9700
N3—C9	1.315 (4)	C8—H8A	0.9600
N3—C11	1.448 (4)	C8—H8B	0.9600
N3—C10	1.449 (4)	C8—H8C	0.9600
O1—C1	1.222 (3)	C9—H9	0.9300
O2—C1	1.305 (3)	C10—H10A	0.9600
O2—H2A	0.8200	C10—H10B	0.9600
O3—C4	1.253 (4)	C10—H10C	0.9600
O4—C4	1.247 (3)	C11—H11A	0.9600
O5—H5A	0.8499	C11—H11B	0.9600
O5—H5B	0.8500	C11—H11C	0.9600
O6—C9	1.226 (4)
N1i—Cu1—N1	180.00 (6)	N1—C5—N2	109.4 (2)
N1i—Cu1—O5i	91.57 (9)	N1—C5—C6	127.0 (3)
N1—Cu1—O5i	88.44 (9)	N2—C5—C6	123.6 (3)
N1i—Cu1—O5	88.43 (9)	C5—C6—C7	113.2 (3)
N1—Cu1—O5	91.56 (9)	C5—C6—H6A	108.9
O5i—Cu1—O5	180.0	C7—C6—H6A	108.9
N1i—Cu1—O1	104.94 (8)	C5—C6—H6B	108.9
N1—Cu1—O1	75.06 (8)	C7—C6—H6B	108.9
O5i—Cu1—O1	92.58 (8)	H6A—C6—H6B	107.7
O5—Cu1—O1	87.42 (8)	C8—C7—C6	114.9 (3)
C5—N1—C2	106.6 (2)	C8—C7—H7A	108.6
C5—N1—Cu1	134.39 (19)	C6—C7—H7A	108.6
C2—N1—Cu1	118.83 (18)	C8—C7—H7B	108.6
C5—N2—C3	109.7 (2)	C6—C7—H7B	108.6
C5—N2—H2	125.2	H7A—C7—H7B	107.5
C3—N2—H2	125.2	C7—C8—H8A	109.5
C9—N3—C11	119.9 (3)	C7—C8—H8B	109.5
C9—N3—C10	120.6 (3)	H8A—C8—H8B	109.5
C11—N3—C10	119.1 (3)	C7—C8—H8C	109.5
C1—O1—Cu1	108.15 (18)	H8A—C8—H8C	109.5
C1—O2—H2A	109.5	H8B—C8—H8C	109.5
Cu1—O5—H5A	114.3	O6—C9—N3	124.8 (3)
Cu1—O5—H5B	113.0	O6—C9—H9	117.6
H5A—O5—H5B	107.6	N3—C9—H9	117.6
O1—C1—O2	122.2 (3)	N3—C10—H10A	109.5
O1—C1—C2	119.7 (3)	N3—C10—H10B	109.5
O2—C1—C2	118.1 (2)	H10A—C10—H10B	109.5
C3—C2—N1	109.4 (2)	N3—C10—H10C	109.5
C3—C2—C1	132.5 (3)	H10A—C10—H10C	109.5
N1—C2—C1	118.1 (2)	H10B—C10—H10C	109.5
N2—C3—C2	104.9 (2)	N3—C11—H11A	109.5
N2—C3—C4	122.9 (2)	N3—C11—H11B	109.5
C2—C3—C4	132.2 (3)	H11A—C11—H11B	109.5
O4—C4—O3	125.3 (3)	N3—C11—H11C	109.5
O4—C4—C3	117.8 (3)	H11A—C11—H11C	109.5
O3—C4—C3	116.9 (3)	H11B—C11—H11C	109.5
O5i—Cu1—N1—C5	85.3 (3)	C5—N2—C3—C4	−177.9 (3)
O5—Cu1—N1—C5	−94.7 (3)	N1—C2—C3—N2	−0.5 (3)
O1—Cu1—N1—C5	178.4 (3)	C1—C2—C3—N2	−178.9 (3)
O5i—Cu1—N1—C2	−89.3 (2)	N1—C2—C3—C4	177.8 (3)
O5—Cu1—N1—C2	90.7 (2)	C1—C2—C3—C4	−0.7 (5)
O1—Cu1—N1—C2	3.76 (19)	N2—C3—C4—O4	0.3 (4)
N1i—Cu1—O1—C1	177.7 (2)	C2—C3—C4—O4	−177.7 (3)
N1—Cu1—O1—C1	−2.3 (2)	N2—C3—C4—O3	179.4 (3)
O5i—Cu1—O1—C1	85.4 (2)	C2—C3—C4—O3	1.4 (5)
O5—Cu1—O1—C1	−94.6 (2)	C2—N1—C5—N2	0.1 (3)
Cu1—O1—C1—O2	179.8 (2)	Cu1—N1—C5—N2	−175.00 (19)
Cu1—O1—C1—C2	0.4 (3)	C2—N1—C5—C6	−178.0 (3)
C5—N1—C2—C3	0.3 (3)	Cu1—N1—C5—C6	6.9 (5)
Cu1—N1—C2—C3	176.24 (18)	C3—N2—C5—N1	−0.4 (3)
C5—N1—C2—C1	179.0 (2)	C3—N2—C5—C6	177.8 (3)
Cu1—N1—C2—C1	−5.1 (3)	N1—C5—C6—C7	112.5 (4)
O1—C1—C2—C3	−179.0 (3)	N2—C5—C6—C7	−65.4 (4)
O2—C1—C2—C3	1.7 (5)	C5—C6—C7—C8	−177.7 (3)
O1—C1—C2—N1	2.7 (4)	C11—N3—C9—O6	−2.4 (6)
O2—C1—C2—N1	−176.7 (2)	C10—N3—C9—O6	−175.2 (4)
C5—N2—C3—C2	0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O6ii	0.86	1.83	2.679 (3)	167
O2—H2A···O3	0.82	1.67	2.494 (3)	177
O5—H5A···O4iii	0.85	1.91	2.755 (3)	172
O5—H5B···O4iv	0.85	2.07	2.906 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O6i	0.86	1.83	2.679 (3)	167
O2—H2A⋯O3	0.82	1.67	2.494 (3)	177
O5—H5A⋯O4ii	0.85	1.91	2.755 (3)	172
O5—H5B⋯O4iii	0.85	2.07	2.906 (3)	167

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