Diaqua-bis-(5-carb-oxy-2-ethyl-1H-imidazole-5-carboxyl-ato-κN,O)zinc trihydrate.

In the crystal structure of the title compound, [Zn(C(7)H(7)N(2)O(4))(2)(H(2)O)(2)]·3H(2)O, the Zn(II) ion, located an inversion center, is N,O-chelated by two 5-carb-oxy-2-ethyl-1H-imidazole-4-carboxyl-ate anions and further coordinated by two water mol-ecules in a distorted octa-hedral geometry. The carb-oxy group links with the carboxyl-ate group of the same ligand via an intra-molecular O-H⋯O hydrogen bond. An extensive inter-molecular N-H⋯O and O-H⋯O hydrogen-bonded network exists in the crystal structure. One disordered lattice water mol-ecule is half-occupied and is located close to an inversion center.

Related literature

For coordination polymers built from 2-ethyl-4,5-imidazole­dicarboxyl­ate, see: Li et al. (2011 ▶); Wang et al. (2008 ▶); Zhang et al. (2010 ▶).

Experimental

Crystal data

[Zn(C7H7N2O4)2(H2O)2]·3H2O

M = 521.74

Triclinic,

a = 7.229 (1) Å

b = 8.8959 (12) Å

c = 9.3541 (15) Å

α = 65.769 (1)°

β = 88.587 (2)°

γ = 70.676 (1)°

V = 513.31 (13) Å3

Z = 1

Mo Kα radiation

μ = 1.27 mm−1

T = 298 K

0.24 × 0.22 × 0.21 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.750, T max = 0.776

2676 measured reflections

1774 independent reflections

1532 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.119

S = 1.09

1774 reflections

152 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.71 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681101676X/xu5200sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101676X/xu5200Isup2.hkl

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

[Zn(C7H7N2O4)2(H2O)2]·3H2O	Z = 1
Mr = 521.74	F(000) = 270
Triclinic, P1	Dx = 1.688 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.229 (1) Å	Cell parameters from 1329 reflections
b = 8.8959 (12) Å	θ = 2.4–26.5°
c = 9.3541 (15) Å	µ = 1.27 mm−1
α = 65.769 (1)°	T = 298 K
β = 88.587 (2)°	Block, colorless
γ = 70.676 (1)°	0.24 × 0.22 × 0.21 mm
V = 513.31 (13) Å3

Bruker SMART 1000 CCD area-detector diffractometer	1774 independent reflections
Radiation source: fine-focus sealed tube	1532 reflections with I > 2σ(I)
graphite	Rint = 0.015
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −8→8
Tmin = 0.750, Tmax = 0.776	k = −8→10
2676 measured reflections	l = −10→11

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0572P)2 + 0.7163P] where P = (Fo2 + 2Fc2)/3
1774 reflections	(Δ/σ)max = 0.001
152 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.71 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	Occ. (<1)
Zn1	0.5000	0.5000	0.5000	0.0323 (2)
N1	0.3641 (4)	0.6476 (4)	0.6256 (3)	0.0279 (7)
N2	0.2272 (4)	0.7940 (4)	0.7637 (4)	0.0323 (7)
H2	0.1798	0.8155	0.8413	0.039*
O1	0.4472 (4)	0.7653 (3)	0.3230 (3)	0.0387 (6)
O2	0.3323 (5)	1.0446 (4)	0.2846 (3)	0.0471 (8)
O3	0.1810 (4)	1.2103 (3)	0.4395 (3)	0.0459 (7)
H3	0.2405	1.1501	0.3944	0.069*
O4	0.0686 (4)	1.1604 (4)	0.6715 (4)	0.0461 (7)
O5	0.7784 (4)	0.4784 (4)	0.5890 (4)	0.0511 (8)
H5C	0.8109	0.5636	0.5848	0.061*
H5D	0.8821	0.3872	0.6159	0.061*
O6	0.1656 (5)	0.8359 (5)	0.0415 (4)	0.0734 (11)
H6E	0.1063	0.8394	0.1212	0.088*
H6F	0.1745	0.9376	−0.0026	0.088*
O7	0.439 (3)	0.987 (4)	0.987 (3)	0.169 (9)	0.50
H7F	0.4629	0.9037	1.0795	0.202*	0.50
H7G	0.5168	0.9516	0.9288	0.202*	0.50
C1	0.3691 (5)	0.8809 (5)	0.3702 (4)	0.0310 (8)
C2	0.3209 (5)	0.8245 (4)	0.5336 (4)	0.0274 (8)
C3	0.2351 (5)	0.9175 (5)	0.6180 (4)	0.0290 (8)
C4	0.1541 (6)	1.1095 (5)	0.5770 (5)	0.0343 (9)
C5	0.3068 (5)	0.6320 (5)	0.7650 (4)	0.0304 (8)
C6	0.3164 (6)	0.4663 (5)	0.9015 (5)	0.0386 (9)
H6A	0.2978	0.4874	0.9956	0.046*
H6B	0.4466	0.3783	0.9188	0.046*
C7	0.1624 (8)	0.3961 (7)	0.8768 (6)	0.0579 (13)
H7A	0.1874	0.3649	0.7895	0.087*
H7B	0.0336	0.4849	0.8544	0.087*
H7C	0.1681	0.2938	0.9706	0.087*

	U11	U22	U33	U12	U13	U23
Zn1	0.0374 (4)	0.0234 (3)	0.0368 (4)	−0.0042 (3)	0.0041 (3)	−0.0184 (3)
N1	0.0294 (16)	0.0241 (15)	0.0311 (16)	−0.0060 (12)	0.0031 (12)	−0.0152 (13)
N2	0.0336 (17)	0.0309 (17)	0.0357 (17)	−0.0051 (14)	0.0058 (13)	−0.0222 (14)
O1	0.0490 (17)	0.0309 (14)	0.0351 (15)	−0.0090 (12)	0.0111 (12)	−0.0174 (12)
O2	0.072 (2)	0.0276 (15)	0.0381 (16)	−0.0160 (14)	0.0135 (15)	−0.0120 (13)
O3	0.0598 (19)	0.0240 (14)	0.0548 (19)	−0.0083 (13)	0.0056 (15)	−0.0226 (14)
O4	0.0492 (18)	0.0328 (15)	0.0566 (18)	−0.0010 (13)	0.0059 (14)	−0.0298 (14)
O5	0.0344 (16)	0.0329 (16)	0.090 (2)	−0.0026 (12)	−0.0071 (15)	−0.0364 (17)
O6	0.073 (2)	0.095 (3)	0.055 (2)	−0.014 (2)	0.0122 (18)	−0.047 (2)
O7	0.15 (2)	0.154 (14)	0.125 (11)	−0.022 (16)	0.017 (16)	−0.013 (10)
C1	0.034 (2)	0.0264 (19)	0.034 (2)	−0.0091 (16)	0.0034 (16)	−0.0152 (16)
C2	0.0266 (18)	0.0230 (18)	0.0333 (19)	−0.0067 (14)	−0.0006 (14)	−0.0139 (15)
C3	0.0283 (19)	0.0248 (18)	0.0352 (19)	−0.0064 (15)	0.0006 (15)	−0.0162 (16)
C4	0.032 (2)	0.0264 (19)	0.046 (2)	−0.0056 (16)	−0.0028 (17)	−0.0206 (19)
C5	0.0291 (19)	0.0295 (19)	0.034 (2)	−0.0064 (15)	0.0017 (15)	−0.0170 (16)
C6	0.045 (2)	0.033 (2)	0.033 (2)	−0.0097 (18)	0.0042 (18)	−0.0130 (17)
C7	0.069 (3)	0.058 (3)	0.048 (3)	−0.034 (3)	0.004 (2)	−0.014 (2)

Zn1—N1	2.104 (3)	O5—H5D	0.8499
Zn1—N1i	2.104 (3)	O6—H6E	0.8578
Zn1—O1	2.164 (3)	O6—H6F	0.8502
Zn1—O1i	2.164 (3)	O7—O7ii	1.05 (3)
Zn1—O5	2.116 (3)	O7—H7F	0.8500
Zn1—O5i	2.116 (3)	O7—H7G	0.8500
N1—C5	1.324 (5)	C1—C2	1.473 (5)
N1—C2	1.375 (4)	C2—C3	1.366 (5)
N2—C5	1.358 (5)	C3—C4	1.490 (5)
N2—C3	1.369 (5)	C5—C6	1.483 (5)
N2—H2	0.8600	C6—C7	1.509 (6)
O1—C1	1.243 (4)	C6—H6A	0.9700
O2—C1	1.277 (4)	C6—H6B	0.9700
O3—C4	1.286 (5)	C7—H7A	0.9600
O3—H3	0.8200	C7—H7B	0.9600
O4—C4	1.218 (5)	C7—H7C	0.9600
O5—H5C	0.8501
N1—Zn1—N1i	180.0	H7F—O7—H7G	108.8
N1—Zn1—O5	88.97 (11)	O1—C1—O2	123.1 (3)
N1i—Zn1—O5	91.03 (11)	O1—C1—C2	118.0 (3)
N1—Zn1—O5i	91.03 (11)	O2—C1—C2	118.9 (3)
N1i—Zn1—O5i	88.97 (11)	C3—C2—N1	109.7 (3)
O5—Zn1—O5i	180.00 (16)	C3—C2—C1	131.9 (3)
N1—Zn1—O1	78.99 (10)	N1—C2—C1	118.5 (3)
N1i—Zn1—O1	101.01 (10)	C2—C3—N2	105.4 (3)
O5—Zn1—O1	91.97 (11)	C2—C3—C4	132.7 (4)
O5i—Zn1—O1	88.03 (11)	N2—C3—C4	121.8 (3)
N1—Zn1—O1i	101.01 (10)	O4—C4—O3	124.9 (4)
N1i—Zn1—O1i	78.99 (10)	O4—C4—C3	119.8 (4)
O5—Zn1—O1i	88.03 (11)	O3—C4—C3	115.4 (3)
O5i—Zn1—O1i	91.97 (11)	N1—C5—N2	109.7 (3)
O1—Zn1—O1i	180.00 (11)	N1—C5—C6	126.4 (3)
C5—N1—C2	106.7 (3)	N2—C5—C6	123.8 (3)
C5—N1—Zn1	142.7 (3)	C5—C6—C7	112.4 (3)
C2—N1—Zn1	110.7 (2)	C5—C6—H6A	109.1
C5—N2—C3	108.6 (3)	C7—C6—H6A	109.1
C5—N2—H2	125.7	C5—C6—H6B	109.1
C3—N2—H2	125.7	C7—C6—H6B	109.1
C1—O1—Zn1	113.8 (2)	H6A—C6—H6B	107.9
C4—O3—H3	109.5	C6—C7—H7A	109.5
Zn1—O5—H5C	125.6	C6—C7—H7B	109.5
Zn1—O5—H5D	124.4	H7A—C7—H7B	109.5
H5C—O5—H5D	108.7	C6—C7—H7C	109.5
H6E—O6—H6F	102.5	H7A—C7—H7C	109.5
O7ii—O7—H7F	88.8	H7B—C7—H7C	109.5
O7ii—O7—H7G	79.9
N1i—Zn1—N1—C5	55 (100)	O2—C1—C2—C3	1.8 (6)
O5—Zn1—N1—C5	−87.4 (4)	O1—C1—C2—N1	−0.1 (5)
O5i—Zn1—N1—C5	92.6 (4)	O2—C1—C2—N1	−178.9 (3)
O1—Zn1—N1—C5	−179.6 (4)	N1—C2—C3—N2	0.2 (4)
O1i—Zn1—N1—C5	0.4 (4)	C1—C2—C3—N2	179.6 (4)
N1i—Zn1—N1—C2	−127 (100)	N1—C2—C3—C4	−177.8 (4)
O5—Zn1—N1—C2	90.9 (2)	C1—C2—C3—C4	1.5 (7)
O5i—Zn1—N1—C2	−89.1 (2)	C5—N2—C3—C2	0.0 (4)
O1—Zn1—N1—C2	−1.3 (2)	C5—N2—C3—C4	178.3 (3)
O1i—Zn1—N1—C2	178.7 (2)	C2—C3—C4—O4	173.7 (4)
N1—Zn1—O1—C1	1.4 (3)	N2—C3—C4—O4	−4.1 (5)
N1i—Zn1—O1—C1	−178.6 (3)	C2—C3—C4—O3	−5.9 (6)
O5—Zn1—O1—C1	−87.2 (3)	N2—C3—C4—O3	176.3 (3)
O5i—Zn1—O1—C1	92.8 (3)	C2—N1—C5—N2	0.4 (4)
O1i—Zn1—O1—C1	168 (100)	Zn1—N1—C5—N2	178.7 (3)
Zn1—O1—C1—O2	177.7 (3)	C2—N1—C5—C6	177.6 (3)
Zn1—O1—C1—C2	−1.1 (4)	Zn1—N1—C5—C6	−4.1 (6)
C5—N1—C2—C3	−0.4 (4)	C3—N2—C5—N1	−0.3 (4)
Zn1—N1—C2—C3	−179.3 (2)	C3—N2—C5—C6	−177.5 (3)
C5—N1—C2—C1	−179.8 (3)	N1—C5—C6—C7	−73.4 (5)
Zn1—N1—C2—C1	1.3 (4)	N2—C5—C6—C7	103.4 (4)
O1—C1—C2—C3	−179.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O6iii	0.86	1.95	2.778 (4)	161
O3—H3···O2	0.82	1.65	2.465 (4)	172
O5—H5C···O3iv	0.85	1.95	2.785 (4)	167
O5—H5D···O4v	0.85	1.88	2.713 (4)	166
O6—H6E···O4vi	0.86	2.29	3.145 (5)	175
O6—H6F···O7vii	0.85	2.09	2.664 (17)	125
O7—H7F···O1iii	0.85	2.12	2.93 (3)	160
O7—H7G···O2iv	0.85	2.24	3.06 (3)	160

Table 1

Selected bond lengths (Å)

Zn1—N1	2.104 (3)
Zn1—O1	2.164 (3)
Zn1—O5	2.116 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O6i	0.86	1.95	2.778 (4)	161
O3—H3⋯O2	0.82	1.65	2.465 (4)	172
O5—H5C⋯O3ii	0.85	1.95	2.785 (4)	167
O5—H5D⋯O4iii	0.85	1.88	2.713 (4)	166
O6—H6E⋯O4iv	0.86	2.29	3.145 (5)	175
O6—H6F⋯O7v	0.85	2.09	2.664 (17)	125
O7—H7F⋯O1i	0.85	2.12	2.93 (3)	160
O7—H7G⋯O2ii	0.85	2.24	3.06 (3)	160

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