catena-Poly[[bis-(1-methyl-imidazole-κN)zinc(II)]-μ-isophthalato-κO:O].

In the solid state, the title compound, [Zn(C(8)H(4)O(4))(C(4)H(6)N(2))(2)](n), exhibits the existence of polymeric zigzag chains extending along the a axis. Each Zn(II) ion is coordinated by two N atoms [Zn-N = 1.996 (6) and 2.032 (5) Å] and two O atoms [Zn-O = 1.930 (4) and 1.976 (4) Å] in a distorted tetra-hedral geometry. Weak C-H⋯O inter-actions contribute to the crystal packing stability.

Related literature

In the related zinc compound [Zn(isophthalato)(1-H-imidazole)2] (Yang et al., 2002 ▶), the ZnII ions also have a distorted tetra­hedral environment.

Experimental

Crystal data

[Zn(C8H4O4)(C4H6N2)2]

M = 393.72

Orthorhombic,

a = 9.6820 (19) Å

b = 13.224 (3) Å

c = 26.983 (5) Å

V = 3454.8 (12) Å3

Z = 8

Mo Kα radiation

μ = 1.45 mm−1

T = 293 (2) K

0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

3091 measured reflections

2967 independent reflections

2041 reflections with I > 2σ(I)

R int = 0.035

3 standard reflections every 100 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.207

S = 1.05

2967 reflections

220 parameters

40 restraints

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.61 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989 ▶); 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: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803078X/cv2451sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803078X/cv2451Isup2.hkl

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

[Zn(C8H4O4)(C4H6N2)2]	F(000) = 1616
Mr = 393.72	Dx = 1.514 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 9.6820 (19) Å	θ = 10–14°
b = 13.224 (3) Å	µ = 1.45 mm−1
c = 26.983 (5) Å	T = 293 K
V = 3454.8 (12) Å3	Block, colourless
Z = 8	0.20 × 0.10 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.036
Radiation source: fine-focus sealed tube	θmax = 25.2°, θmin = 1.5°
graphite	h = 0→11
ω scans	k = 0→15
3091 measured reflections	l = 0→32
2967 independent reflections	3 standard reflections every 100 reflections
2041 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.207	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1255P)2] where P = (Fo2 + 2Fc2)/3
2967 reflections	(Δ/σ)max < 0.001
220 parameters	Δρmax = 0.50 e Å−3
40 restraints	Δρmin = −0.61 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
Zn	0.18405 (6)	0.12667 (5)	0.12048 (3)	0.0338 (3)
N1	0.1883 (6)	0.3348 (5)	0.2326 (2)	0.0594 (17)
N2	0.1689 (5)	0.2071 (4)	0.1829 (2)	0.0434 (13)
N3	0.2381 (6)	0.3608 (4)	0.0199 (2)	0.0461 (14)
N4	0.1948 (5)	0.2244 (4)	0.06251 (18)	0.0358 (12)
O1	0.3326 (4)	0.0294 (4)	0.11870 (16)	0.0460 (12)
O2	0.4748 (4)	0.1603 (3)	0.12273 (18)	0.0510 (13)
O3	1.0442 (4)	−0.0567 (4)	0.1520 (2)	0.0680 (16)
O4	−0.0041 (4)	0.0763 (3)	0.10656 (16)	0.0440 (11)
C1	0.2355 (10)	0.4326 (6)	0.2511 (3)	0.081
H1A	0.3017	0.4605	0.2284	0.122*
H1B	0.2777	0.4239	0.2830	0.122*
H1C	0.1581	0.4776	0.2539	0.122*
C2	0.0944 (8)	0.2711 (7)	0.2534 (3)	0.079 (3)
H2A	0.0483	0.2798	0.2833	0.094*
C3	0.0821 (8)	0.1945 (7)	0.2223 (3)	0.071 (2)
H3A	0.0229	0.1399	0.2267	0.086*
C4	0.2306 (8)	0.2910 (6)	0.1911 (2)	0.0523 (18)
H4B	0.2976	0.3181	0.1703	0.063*
C5	0.2982 (8)	0.4589 (5)	0.0065 (3)	0.060 (2)
H5A	0.3727	0.4745	0.0288	0.089*
H5B	0.2287	0.5104	0.0089	0.089*
H5C	0.3326	0.4560	−0.0268	0.089*
C6	0.2723 (6)	0.3054 (5)	0.0588 (2)	0.0408 (15)
H6A	0.3427	0.3218	0.0809	0.049*
C7	0.1029 (8)	0.2310 (5)	0.0239 (3)	0.0568 (19)
H7A	0.0326	0.1849	0.0175	0.068*
C8	0.1294 (8)	0.3137 (5)	−0.0030 (3)	0.059 (2)
H8A	0.0835	0.3349	−0.0315	0.070*
C9	0.9641 (6)	−0.0064 (5)	0.1281 (2)	0.0361 (14)
C10	0.8172 (5)	−0.0403 (5)	0.1219 (2)	0.0328 (14)
C11	0.7891 (7)	−0.1438 (5)	0.1187 (2)	0.0436 (16)
H11A	0.8608	−0.1907	0.1190	0.052*
C12	0.6544 (7)	−0.1755 (5)	0.1151 (3)	0.060 (2)
H12A	0.6356	−0.2443	0.1126	0.072*
C13	0.5473 (7)	−0.1080 (5)	0.1151 (3)	0.0510 (18)
H13A	0.4572	−0.1318	0.1121	0.061*
C14	0.5702 (5)	−0.0054 (4)	0.1195 (2)	0.0301 (12)
C15	0.7082 (5)	0.0286 (4)	0.1222 (2)	0.0321 (13)
H15A	0.7265	0.0975	0.1242	0.039*
C16	0.4545 (6)	0.0702 (5)	0.1210 (2)	0.0340 (14)

	U11	U22	U33	U12	U13	U23
Zn	0.0166 (4)	0.0401 (4)	0.0446 (5)	0.0005 (3)	−0.0007 (3)	0.0023 (3)
N1	0.067 (4)	0.058 (3)	0.053 (3)	−0.018 (3)	0.016 (3)	−0.013 (3)
N2	0.032 (3)	0.056 (3)	0.043 (3)	−0.008 (2)	0.006 (2)	0.001 (2)
N3	0.051 (3)	0.052 (3)	0.035 (3)	−0.008 (3)	0.003 (3)	0.003 (3)
N4	0.024 (2)	0.043 (3)	0.041 (3)	−0.009 (2)	−0.009 (2)	0.006 (2)
O1	0.019 (2)	0.057 (3)	0.062 (3)	0.004 (2)	0.0020 (19)	0.003 (2)
O2	0.021 (2)	0.036 (2)	0.096 (4)	−0.0011 (19)	−0.001 (2)	0.004 (2)
O3	0.023 (2)	0.075 (3)	0.106 (4)	−0.001 (2)	−0.013 (3)	0.041 (3)
O4	0.020 (2)	0.049 (3)	0.063 (3)	−0.0021 (19)	−0.004 (2)	0.008 (2)
C1	0.081	0.081	0.081	0.000	0.000	0.000
C2	0.068 (5)	0.100 (6)	0.068 (5)	−0.024 (4)	0.038 (4)	−0.019 (4)
C3	0.064 (5)	0.081 (5)	0.069 (5)	−0.030 (4)	0.031 (4)	−0.006 (4)
C4	0.052 (4)	0.071 (4)	0.033 (3)	−0.010 (3)	0.015 (3)	−0.005 (3)
C5	0.069 (5)	0.054 (4)	0.056 (5)	−0.010 (4)	0.008 (4)	0.004 (4)
C6	0.034 (3)	0.051 (4)	0.037 (4)	−0.006 (3)	0.001 (3)	0.003 (3)
C7	0.053 (4)	0.054 (4)	0.063 (5)	−0.009 (4)	−0.017 (4)	0.005 (4)
C8	0.061 (5)	0.060 (5)	0.054 (5)	−0.004 (4)	−0.017 (4)	0.017 (4)
C9	0.017 (3)	0.046 (3)	0.045 (4)	0.006 (3)	0.000 (3)	−0.007 (3)
C10	0.011 (3)	0.054 (4)	0.033 (3)	−0.002 (2)	0.002 (2)	0.005 (3)
C11	0.026 (3)	0.041 (4)	0.064 (4)	0.005 (3)	−0.006 (3)	−0.007 (3)
C12	0.029 (4)	0.031 (3)	0.119 (7)	−0.006 (3)	−0.005 (4)	−0.006 (4)
C13	0.024 (3)	0.042 (4)	0.087 (5)	−0.005 (3)	−0.002 (3)	−0.007 (3)
C14	0.015 (3)	0.037 (3)	0.038 (3)	0.002 (2)	−0.004 (2)	0.001 (3)
C15	0.017 (3)	0.034 (3)	0.046 (4)	−0.001 (2)	−0.002 (2)	0.005 (3)
C16	0.012 (3)	0.049 (4)	0.041 (3)	0.001 (3)	0.001 (2)	0.008 (3)

Zn—O1	1.930 (4)	C3—H3A	0.9300
Zn—O4	1.976 (4)	C4—H4B	0.9300
Zn—N2	1.996 (6)	C5—H5A	0.9600
Zn—N4	2.032 (5)	C5—H5B	0.9600
N1—C4	1.327 (8)	C5—H5C	0.9600
N1—C2	1.360 (9)	C6—H6A	0.9300
N1—C1	1.459 (10)	C7—C8	1.339 (9)
N2—C4	1.279 (8)	C7—H7A	0.9300
N2—C3	1.367 (8)	C8—H8A	0.9300
N3—C6	1.322 (8)	C9—O4ii	1.277 (8)
N3—C8	1.371 (9)	C9—C10	1.501 (7)
N3—C5	1.468 (8)	C10—C15	1.395 (8)
N4—C6	1.311 (7)	C10—C11	1.399 (9)
N4—C7	1.372 (8)	C11—C12	1.373 (8)
O1—C16	1.299 (7)	C11—H11A	0.9300
O2—C16	1.209 (8)	C12—C13	1.368 (9)
O3—C9	1.207 (7)	C12—H12A	0.9300
O4—C9i	1.277 (8)	C13—C14	1.381 (8)
C1—H1A	0.9600	C13—H13A	0.9300
C1—H1B	0.9600	C14—C15	1.411 (7)
C1—H1C	0.9600	C14—C16	1.502 (8)
C2—C3	1.319 (11)	C15—H15A	0.9300
C2—H2A	0.9300
O1—Zn—O4	117.23 (19)	H5A—C5—H5B	109.5
O1—Zn—N2	115.5 (2)	N3—C5—H5C	109.5
O4—Zn—N2	105.80 (19)	H5A—C5—H5C	109.5
O1—Zn—N4	111.51 (19)	H5B—C5—H5C	109.5
O4—Zn—N4	96.63 (18)	N4—C6—N3	111.7 (6)
N2—Zn—N4	108.3 (2)	N4—C6—H6A	124.2
C4—N1—C2	106.5 (6)	N3—C6—H6A	124.2
C4—N1—C1	125.3 (7)	C8—C7—N4	109.9 (6)
C2—N1—C1	128.2 (7)	C8—C7—H7A	125.1
C4—N2—C3	104.9 (6)	N4—C7—H7A	125.1
C4—N2—Zn	125.0 (5)	C7—C8—N3	105.8 (6)
C3—N2—Zn	129.6 (5)	C7—C8—H8A	127.1
C6—N3—C8	107.4 (5)	N3—C8—H8A	127.1
C6—N3—C5	125.9 (6)	O3—C9—O4ii	124.1 (6)
C8—N3—C5	126.5 (6)	O3—C9—C10	120.2 (6)
C6—N4—C7	105.2 (5)	O4ii—C9—C10	115.7 (5)
C6—N4—Zn	127.4 (4)	C15—C10—C11	119.5 (5)
C7—N4—Zn	126.2 (4)	C15—C10—C9	121.5 (6)
C16—O1—Zn	113.5 (4)	C11—C10—C9	118.9 (5)
C9i—O4—Zn	115.1 (4)	C12—C11—C10	119.2 (6)
N1—C1—H1A	109.5	C12—C11—H11A	120.4
N1—C1—H1B	109.5	C10—C11—H11A	120.4
H1A—C1—H1B	109.5	C13—C12—C11	121.4 (6)
N1—C1—H1C	109.5	C13—C12—H12A	119.3
H1A—C1—H1C	109.5	C11—C12—H12A	119.3
H1B—C1—H1C	109.5	C12—C13—C14	121.2 (6)
C3—C2—N1	105.9 (7)	C12—C13—H13A	119.4
C3—C2—H2A	127.0	C14—C13—H13A	119.4
N1—C2—H2A	127.0	C13—C14—C15	118.0 (5)
C2—C3—N2	110.2 (7)	C13—C14—C16	122.4 (5)
C2—C3—H3A	124.9	C15—C14—C16	119.5 (5)
N2—C3—H3A	124.9	C10—C15—C14	120.5 (5)
N2—C4—N1	112.4 (6)	C10—C15—H15A	119.7
N2—C4—H4B	123.8	C14—C15—H15A	119.7
N1—C4—H4B	123.8	O2—C16—O1	124.0 (6)
N3—C5—H5A	109.5	O2—C16—C14	122.4 (5)
N3—C5—H5B	109.5	O1—C16—C14	113.6 (5)
O1—Zn—N2—C4	89.0 (6)	Zn—N4—C6—N3	−169.7 (4)
O4—Zn—N2—C4	−139.6 (6)	C8—N3—C6—N4	0.9 (8)
N4—Zn—N2—C4	−36.9 (6)	C5—N3—C6—N4	176.2 (6)
O1—Zn—N2—C3	−100.1 (7)	C6—N4—C7—C8	1.9 (8)
O4—Zn—N2—C3	31.4 (7)	Zn—N4—C7—C8	170.1 (5)
N4—Zn—N2—C3	134.1 (7)	N4—C7—C8—N3	−1.4 (9)
O1—Zn—N4—C6	−81.7 (5)	C6—N3—C8—C7	0.3 (9)
O4—Zn—N4—C6	155.6 (5)	C5—N3—C8—C7	−175.0 (6)
N2—Zn—N4—C6	46.5 (6)	O3—C9—C10—C15	141.9 (7)
O1—Zn—N4—C7	112.7 (6)	O4ii—C9—C10—C15	−38.6 (9)
O4—Zn—N4—C7	−10.0 (6)	O3—C9—C10—C11	−34.3 (9)
N2—Zn—N4—C7	−119.1 (6)	O4ii—C9—C10—C11	145.2 (6)
O4—Zn—O1—C16	170.5 (4)	C15—C10—C11—C12	1.0 (10)
N2—Zn—O1—C16	−63.7 (4)	C9—C10—C11—C12	177.3 (6)
N4—Zn—O1—C16	60.4 (4)	C10—C11—C12—C13	−0.7 (12)
O1—Zn—O4—C9i	44.5 (5)	C11—C12—C13—C14	−1.0 (12)
N2—Zn—O4—C9i	−86.0 (4)	C12—C13—C14—C15	2.4 (11)
N4—Zn—O4—C9i	162.9 (4)	C12—C13—C14—C16	−178.4 (6)
C4—N1—C2—C3	−2.1 (10)	C11—C10—C15—C14	0.3 (9)
C1—N1—C2—C3	177.6 (8)	C9—C10—C15—C14	−175.9 (5)
N1—C2—C3—N2	1.5 (11)	C13—C14—C15—C10	−2.0 (10)
C4—N2—C3—C2	−0.2 (10)	C16—C14—C15—C10	178.7 (5)
Zn—N2—C3—C2	−172.6 (6)	Zn—O1—C16—O2	−1.8 (8)
C3—N2—C4—N1	−1.2 (9)	Zn—O1—C16—C14	−180.0 (4)
Zn—N2—C4—N1	171.6 (5)	C13—C14—C16—O2	−176.8 (7)
C2—N1—C4—N2	2.1 (9)	C15—C14—C16—O2	2.4 (9)
C1—N1—C4—N2	−177.6 (7)	C13—C14—C16—O1	1.4 (8)
C7—N4—C6—N3	−1.7 (7)	C15—C14—C16—O1	−179.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O3iii	0.96	2.55	3.423 (10)	150
C4—H4B···O3iii	0.93	2.31	3.150 (9)	150
C11—H11A···O2iv	0.93	2.54	3.457 (8)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O3i	0.96	2.55	3.423 (10)	150
C4—H4B⋯O3i	0.93	2.31	3.150 (9)	150
C11—H11A⋯O2ii	0.93	2.54	3.457 (8)	171

Symmetry codes: (i) ; (ii) .