trans-Diaqua-bis-[5-carb-oxy-4-carboxyl-ato-2-(4-pyridinio)-1H-imidazol-1-ido-κN,O]zinc(II).

In the title complex, [Zn(C(10)H(6)N(3)O(4))(2)(H(2)O)(2)], the Zn(II) atom is located on a twofold rotation axis and is coordinated by two trans-positioned N,O-bidentate and zwitterionic 5-carb-oxy-4-carboxyl-ato-2-(4-pyridinio)-1H-imidazol-1-ide (H(2)PIDC(-)) ligands and two water mol-ecules, defining a distorted octa-hedral environment. The complete solid-state structure can be described as a three-dimensional supra-molecular framework, stabilized by extensive hydrogen-bonding inter-actions involving the coordinated water mol-ecules, uncoordin-ated imidazole N atom, protonated pyridine N and carboxyl-ate O atoms of the H(2)PIDC(-) ligands.

Related literature

For related structures, see: Li, Liu et al. (2009 ▶); Li, Wu et al. (2009 ▶). For the preparation of 2-(pyridin-4-yl)-1H-imidazole-4,5-dicarb­oxy­lic acid, see: Sun et al. (2006 ▶).

Experimental

Crystal data

[Zn(C10H6N3O4)2(H2O)2]

M = 565.76

Monoclinic,

a = 7.4138 (9) Å

b = 20.204 (3) Å

c = 13.4778 (17) Å

β = 97.008 (1)°

V = 2003.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.31 mm−1

T = 173 K

0.27 × 0.17 × 0.10 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2000 ▶) T min = 0.754, T max = 0.878

9235 measured reflections

2488 independent reflections

1957 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.090

S = 1.04

2488 reflections

178 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.37 e Å−3

Data collection: CrystalClear (Rigaku, 2000 ▶); 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 (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810031855/jh2196sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031855/jh2196Isup2.hkl

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

[Zn(C10H6N3O4)2(H2O)2]	F(000) = 1152
Mr = 565.76	Dx = 1.875 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.4138 (9) Å	θ = 2.5–28.3°
b = 20.204 (3) Å	µ = 1.31 mm−1
c = 13.4778 (17) Å	T = 173 K
β = 97.008 (1)°	Block, colorless
V = 2003.7 (4) Å3	0.27 × 0.17 × 0.10 mm
Z = 4

Rigaku Mercury CCD diffractometer	2488 independent reflections
Radiation source: fine-focus sealed tube	1957 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω scan	θmax = 28.3°, θmin = 2.5°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	h = −9→9
Tmin = 0.754, Tmax = 0.878	k = −26→26
9235 measured reflections	l = −17→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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0453P)2 + 2.1588P] where P = (Fo2 + 2Fc2)/3
2488 reflections	(Δ/σ)max < 0.001
178 parameters	Δρmax = 0.34 e Å−3
1 restraint	Δρmin = −0.37 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
Zn1	0.2500	0.2500	0.5000	0.02158 (12)
O1	0.1031 (3)	0.21527 (11)	0.36331 (14)	0.0405 (5)
N1	−0.0003 (2)	0.26283 (8)	0.56460 (13)	0.0181 (3)
C1	0.0872 (3)	0.37351 (10)	0.51444 (16)	0.0230 (4)
O2	0.1956 (2)	0.34788 (7)	0.46161 (13)	0.0296 (4)
N2	−0.2095 (2)	0.28420 (8)	0.67035 (13)	0.0204 (4)
C2	−0.2007 (3)	0.40644 (10)	0.68011 (17)	0.0239 (4)
O3	0.0612 (2)	0.43586 (7)	0.51721 (13)	0.0355 (4)
N3	−0.2067 (3)	0.03644 (9)	0.68078 (15)	0.0283 (4)
H3	−0.2203	−0.0056	0.6953	0.034*
C3	−0.0184 (3)	0.32960 (9)	0.57348 (15)	0.0184 (4)
O4	−0.1528 (3)	0.46001 (7)	0.63823 (14)	0.0368 (4)
C4	−0.1451 (3)	0.34251 (9)	0.63948 (15)	0.0192 (4)
O5	−0.2869 (2)	0.40756 (8)	0.75300 (12)	0.0322 (4)
C5	−0.1194 (3)	0.23786 (9)	0.62332 (15)	0.0184 (4)
C6	−0.1542 (3)	0.16745 (9)	0.63892 (15)	0.0180 (4)
C7	−0.2469 (3)	0.14843 (10)	0.71861 (17)	0.0250 (5)
H7	−0.2949	0.1811	0.7587	0.030*
C8	−0.2687 (3)	0.08256 (11)	0.73901 (17)	0.0278 (5)
H8	−0.3279	0.0698	0.7946	0.033*
C9	−0.1247 (3)	0.05237 (11)	0.60116 (18)	0.0311 (5)
H9	−0.0866	0.0184	0.5597	0.037*
C10	−0.0947 (3)	0.11772 (10)	0.57857 (17)	0.0251 (5)
H10	−0.0343	0.1288	0.5226	0.030*
H1B	−0.008 (4)	0.2148 (13)	0.353 (2)	0.030*
H1A	0.135 (4)	0.1903 (13)	0.324 (2)	0.030*
H4A	−0.080 (3)	0.4538 (12)	0.5916 (16)	0.030*

	U11	U22	U33	U12	U13	U23
Zn1	0.0248 (2)	0.01734 (18)	0.0245 (2)	0.00358 (13)	0.01053 (13)	0.00102 (13)
O1	0.0245 (9)	0.0669 (14)	0.0305 (10)	0.0044 (9)	0.0054 (8)	−0.0200 (9)
N1	0.0208 (8)	0.0139 (8)	0.0206 (8)	0.0008 (6)	0.0066 (7)	0.0011 (6)
C1	0.0266 (11)	0.0175 (10)	0.0261 (11)	0.0015 (8)	0.0088 (9)	0.0026 (8)
O2	0.0361 (9)	0.0201 (7)	0.0366 (9)	0.0046 (7)	0.0203 (7)	0.0067 (7)
N2	0.0216 (9)	0.0161 (8)	0.0250 (9)	−0.0002 (7)	0.0085 (7)	−0.0004 (7)
C2	0.0263 (11)	0.0184 (10)	0.0280 (11)	0.0016 (8)	0.0077 (9)	−0.0012 (8)
O3	0.0493 (11)	0.0144 (7)	0.0482 (11)	0.0022 (7)	0.0275 (9)	0.0071 (7)
N3	0.0356 (11)	0.0140 (8)	0.0359 (11)	−0.0042 (7)	0.0074 (8)	0.0035 (7)
C3	0.0209 (10)	0.0140 (9)	0.0212 (10)	0.0006 (7)	0.0063 (8)	0.0004 (7)
O4	0.0576 (12)	0.0155 (7)	0.0430 (10)	0.0036 (7)	0.0291 (9)	−0.0001 (7)
C4	0.0222 (10)	0.0144 (9)	0.0220 (10)	0.0007 (7)	0.0062 (8)	0.0013 (7)
O5	0.0417 (10)	0.0220 (8)	0.0370 (9)	0.0018 (7)	0.0215 (8)	−0.0053 (7)
C5	0.0204 (10)	0.0153 (9)	0.0199 (10)	−0.0008 (7)	0.0045 (8)	0.0015 (7)
C6	0.0186 (10)	0.0145 (9)	0.0213 (10)	−0.0013 (7)	0.0034 (8)	0.0016 (7)
C7	0.0309 (12)	0.0183 (10)	0.0275 (11)	−0.0017 (8)	0.0101 (9)	−0.0008 (8)
C8	0.0324 (12)	0.0239 (11)	0.0287 (12)	−0.0055 (9)	0.0109 (10)	0.0054 (9)
C9	0.0411 (14)	0.0190 (10)	0.0353 (13)	−0.0016 (9)	0.0137 (10)	−0.0037 (9)
C10	0.0312 (12)	0.0195 (10)	0.0266 (11)	−0.0023 (8)	0.0115 (9)	−0.0011 (8)

Zn1—O2	2.0713 (15)	C2—O4	1.290 (3)
Zn1—O2i	2.0713 (15)	C2—C4	1.481 (3)
Zn1—O1	2.1407 (18)	N3—C9	1.336 (3)
Zn1—O1i	2.1407 (18)	N3—C8	1.335 (3)
Zn1—N1i	2.1592 (17)	N3—H3	0.8800
Zn1—N1	2.1592 (17)	C3—C4	1.395 (3)
O1—H1B	0.82 (3)	O4—H4A	0.885 (16)
O1—H1A	0.78 (3)	C5—C6	1.466 (2)
N1—C5	1.353 (3)	C6—C7	1.398 (3)
N1—C3	1.362 (2)	C6—C10	1.397 (3)
C1—O2	1.249 (3)	C7—C8	1.372 (3)
C1—O3	1.276 (2)	C7—H7	0.9500
C1—C3	1.478 (3)	C8—H8	0.9500
N2—C5	1.352 (3)	C9—C10	1.379 (3)
N2—C4	1.355 (2)	C9—H9	0.9500
C2—O5	1.236 (3)	C10—H10	0.9500
O2—Zn1—O2i	180.0	C9—N3—C8	121.80 (19)
O2—Zn1—O1	92.00 (8)	C9—N3—H3	119.1
O2i—Zn1—O1	88.00 (8)	C8—N3—H3	119.1
O2—Zn1—O1i	88.00 (8)	N1—C3—C4	108.82 (17)
O2i—Zn1—O1i	92.00 (8)	N1—C3—C1	118.85 (17)
O1—Zn1—O1i	180.0	C4—C3—C1	132.32 (18)
O2—Zn1—N1i	99.47 (6)	C2—O4—H4A	114.6 (16)
O2i—Zn1—N1i	80.53 (6)	N2—C4—C3	108.85 (17)
O1—Zn1—N1i	89.17 (7)	N2—C4—C2	121.34 (18)
O1i—Zn1—N1i	90.83 (7)	C3—C4—C2	129.67 (18)
O2—Zn1—N1	80.53 (6)	N1—C5—N2	114.27 (17)
O2i—Zn1—N1	99.47 (6)	N1—C5—C6	125.79 (18)
O1—Zn1—N1	90.83 (7)	N2—C5—C6	119.94 (18)
O1i—Zn1—N1	89.17 (7)	C7—C6—C10	117.99 (18)
N1i—Zn1—N1	180.0	C7—C6—C5	119.26 (18)
Zn1—O1—H1B	123.2 (19)	C10—C6—C5	122.73 (18)
Zn1—O1—H1A	129 (2)	C8—C7—C6	120.1 (2)
H1B—O1—H1A	105 (3)	C8—C7—H7	120.0
C5—N1—C3	103.85 (16)	C6—C7—H7	120.0
C5—N1—Zn1	147.69 (13)	N3—C8—C7	120.1 (2)
C3—N1—Zn1	104.67 (12)	N3—C8—H8	119.9
O2—C1—O3	122.40 (19)	C7—C8—H8	119.9
O2—C1—C3	118.55 (18)	N3—C9—C10	120.6 (2)
O3—C1—C3	119.02 (18)	N3—C9—H9	119.7
C1—O2—Zn1	111.87 (13)	C10—C9—H9	119.7
C5—N2—C4	104.20 (17)	C9—C10—C6	119.3 (2)
O5—C2—O4	121.93 (19)	C9—C10—H10	120.4
O5—C2—C4	120.28 (19)	C6—C10—H10	120.4
O4—C2—C4	117.77 (19)
O2—Zn1—N1—C5	−170.7 (3)	N1—C3—C4—N2	−1.3 (2)
O2i—Zn1—N1—C5	9.3 (3)	C1—C3—C4—N2	177.0 (2)
O1—Zn1—N1—C5	97.4 (3)	N1—C3—C4—C2	174.4 (2)
O1i—Zn1—N1—C5	−82.6 (3)	C1—C3—C4—C2	−7.3 (4)
N1i—Zn1—N1—C5	37 (16)	O5—C2—C4—N2	10.2 (3)
O2—Zn1—N1—C3	−19.40 (13)	O4—C2—C4—N2	−171.3 (2)
O2i—Zn1—N1—C3	160.60 (13)	O5—C2—C4—C3	−165.1 (2)
O1—Zn1—N1—C3	−111.28 (14)	O4—C2—C4—C3	13.5 (4)
O1i—Zn1—N1—C3	68.72 (14)	C3—N1—C5—N2	−1.2 (2)
N1i—Zn1—N1—C3	−171 (100)	Zn1—N1—C5—N2	150.2 (2)
O3—C1—O2—Zn1	166.35 (18)	C3—N1—C5—C6	179.3 (2)
C3—C1—O2—Zn1	−15.4 (3)	Zn1—N1—C5—C6	−29.3 (4)
O2i—Zn1—O2—C1	24 (100)	C4—N2—C5—N1	0.4 (2)
O1—Zn1—O2—C1	110.06 (17)	C4—N2—C5—C6	179.97 (19)
O1i—Zn1—O2—C1	−69.94 (17)	N1—C5—C6—C7	164.9 (2)
N1i—Zn1—O2—C1	−160.45 (16)	N2—C5—C6—C7	−14.7 (3)
N1—Zn1—O2—C1	19.55 (16)	N1—C5—C6—C10	−13.6 (3)
C5—N1—C3—C4	1.5 (2)	N2—C5—C6—C10	166.9 (2)
Zn1—N1—C3—C4	−163.20 (14)	C10—C6—C7—C8	3.5 (3)
C5—N1—C3—C1	−177.10 (19)	C5—C6—C7—C8	−175.1 (2)
Zn1—N1—C3—C1	18.2 (2)	C9—N3—C8—C7	−0.8 (4)
O2—C1—C3—N1	−3.1 (3)	C6—C7—C8—N3	−2.2 (3)
O3—C1—C3—N1	175.2 (2)	C8—N3—C9—C10	2.6 (4)
O2—C1—C3—C4	178.8 (2)	N3—C9—C10—C6	−1.2 (4)
O3—C1—C3—C4	−3.0 (4)	C7—C6—C10—C9	−1.8 (3)
C5—N2—C4—C3	0.6 (2)	C5—C6—C10—C9	176.7 (2)
C5—N2—C4—C2	−175.55 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···N2ii	0.82 (3)	2.08 (3)	2.898 (3)	178 (3)
N3—H3···O5iii	0.88	1.89	2.755 (2)	169.
O4—H4A···O3	0.89 (2)	1.58 (2)	2.459 (2)	173 (3)

Table 1

Selected bond lengths (Å)

Zn1—O2	2.0713 (15)
Zn1—O1	2.1407 (18)
Zn1—N1	2.1592 (17)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯N2i	0.82 (3)	2.08 (3)	2.898 (3)	178 (3)
N3—H3⋯O5ii	0.88	1.89	2.755 (2)	169
O4—H4A⋯O3	0.89 (2)	1.58 (2)	2.459 (2)	173 (3)

Symmetry codes: (i) ; (ii) .