Poly[[μ(2)-1,2-bis-(1H-imidazol-1-ylmeth-yl)benzene-κN:N](μ(2)-tereph-thalato-κO:O)zinc(II)].

In the title coordination polymer, [Zn(C(8)H(4)O(4))(C(14)H(14)N(4))](n), the Zn(II) atom is coordinated by two N atoms from two 1,2-bis-(imidazol-1-ylmeth-yl)benzene ligands as well as by the two O atoms from two terephthalate ligands, confering a tetra-hedral coordination geometry. The bridging ligands generate a three-dimensional structure.

Related literature

For related structures, see: Fan et al. (2005 ▶, 2006 ▶); Liu et al. (2007 ▶, 2008a ▶,b ▶, 2009 ▶); Yang et al. (2008 ▶).

Experimental

Crystal data

[Zn(C8H4O4)(C14H14N4)]

M = 467.79

Triclinic,

a = 10.132 (3) Å

b = 10.179 (3) Å

c = 11.169 (3) Å

α = 99.073 (4)°

β = 102.748 (4)°

γ = 112.974 (4)°

V = 995.5 (5) Å3

Z = 2

Mo Kα radiation

μ = 1.27 mm−1

T = 291 K

0.20 × 0.16 × 0.10 mm

Data collection

Bruker SMART area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.785, T max = 0.883

7505 measured reflections

3674 independent reflections

3140 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.097

S = 1.05

3674 reflections

298 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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/S1600536810042406/ng5050sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042406/ng5050Isup2.hkl

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

[Zn(C8H4O4)(C14H14N4)]	Z = 2
Mr = 467.79	F(000) = 480
Triclinic, P1	Dx = 1.561 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.132 (3) Å	Cell parameters from 1793 reflections
b = 10.179 (3) Å	θ = 1.9–25.5°
c = 11.169 (3) Å	µ = 1.27 mm−1
α = 99.073 (4)°	T = 291 K
β = 102.748 (4)°	Block, yellow
γ = 112.974 (4)°	0.20 × 0.16 × 0.10 mm
V = 995.5 (5) Å3

Bruker SMART area-detector diffractometer	3674 independent reflections
Radiation source: fine-focus sealed tube	3140 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 25.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.785, Tmax = 0.883	k = −12→12
7505 measured reflections	l = −13→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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0482P)2 + 0.0138P] where P = (Fo2 + 2Fc2)/3
3674 reflections	(Δ/σ)max < 0.001
298 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.23 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	0.72744 (4)	0.03060 (3)	−0.12258 (3)	0.03123 (13)
O1	0.8199 (2)	−0.0226 (2)	−0.24812 (18)	0.0371 (5)
O2	0.9037 (2)	0.2104 (2)	−0.2633 (2)	0.0458 (6)
O3	0.5956 (2)	−0.1577 (2)	−0.0977 (2)	0.0459 (6)
O4	0.8048 (3)	−0.1373 (2)	0.0314 (3)	0.0560 (6)
N1	0.5722 (3)	0.0954 (3)	−0.2066 (2)	0.0348 (6)
N2	0.8687 (3)	0.1981 (2)	0.0314 (2)	0.0337 (6)
N6	1.0855 (3)	0.3509 (3)	0.1741 (2)	0.0360 (6)
N9	0.4735 (3)	0.2181 (3)	−0.3094 (2)	0.0376 (6)
C1	0.9907 (4)	0.1328 (4)	−0.4772 (3)	0.0455 (8)
H1	0.9858	0.2230	−0.4625	0.073 (12)*
C4	0.8876 (3)	0.0814 (3)	−0.2957 (3)	0.0314 (6)
C6	0.9462 (3)	0.0392 (3)	−0.4010 (3)	0.0319 (7)
C9	0.9965 (3)	0.2102 (3)	0.1035 (3)	0.0360 (7)
H9	1.0222	0.1322	0.1055	0.045 (9)*
C10	0.6685 (4)	−0.2048 (3)	−0.0265 (3)	0.0382 (7)
C11	0.8774 (4)	0.3382 (3)	0.0577 (3)	0.0446 (8)
H11	0.8025	0.3636	0.0203	0.052 (10)*
C13	1.2799 (3)	0.5047 (3)	0.3833 (3)	0.0356 (7)
C18	1.4214 (3)	0.6254 (3)	0.4431 (3)	0.0394 (7)
C20	0.5801 (3)	−0.3584 (3)	−0.0123 (3)	0.0382 (7)
C22	1.3428 (5)	0.6714 (4)	0.6276 (3)	0.0633 (11)
H22	1.3647	0.7271	0.7097	0.067 (11)*
C23	1.1735 (4)	0.4697 (3)	0.4470 (3)	0.0420 (8)
H23	1.0795	0.3895	0.4065	0.035 (8)*
C26	0.5945 (3)	0.1929 (3)	−0.2730 (3)	0.0389 (7)
H26	0.6833	0.2390	−0.2922	0.030 (7)*
C27	0.4285 (3)	0.0549 (3)	−0.2007 (3)	0.0407 (7)
H27	0.3809	−0.0136	−0.1596	0.047 (9)*
C28	0.6533 (4)	−0.4224 (3)	0.0621 (3)	0.0443 (8)
H28	0.7563	−0.3708	0.1043	0.050 (10)*
C31	0.9565 (4)	−0.0932 (3)	−0.4253 (3)	0.0436 (8)
H31	0.9278	−0.1572	−0.3750	0.063 (11)*
C32	0.4269 (4)	−0.4382 (3)	−0.0747 (3)	0.0442 (8)
H32	0.3775	−0.3967	−0.1252	0.058 (10)*
C33	1.2432 (3)	0.4081 (4)	0.2513 (3)	0.0441 (8)
H33A	1.2660	0.3252	0.2594	0.063 (11)*
H33B	1.3073	0.4652	0.2071	0.042 (9)*
C37	1.0093 (4)	0.4329 (3)	0.1455 (3)	0.0443 (8)
H37	1.0422	0.5339	0.1795	0.038 (8)*
C38	1.2048 (4)	0.5524 (4)	0.5688 (3)	0.0547 (9)
H38	1.1325	0.5272	0.6106	0.040 (9)*
C39	1.4495 (4)	0.7073 (4)	0.5666 (3)	0.0562 (10)
H39	1.5423	0.7885	0.6075	0.065 (11)*
C45	0.4583 (3)	0.3249 (4)	−0.3803 (3)	0.0490 (9)
H45A	0.3600	0.2789	−0.4446	0.045 (9)*
H45B	0.4650	0.4104	−0.3222	0.045 (9)*
C46	0.3671 (4)	0.1301 (3)	−0.2636 (3)	0.0431 (8)
H46	0.2710	0.1233	−0.2735	0.052 (10)*

	U11	U22	U33	U12	U13	U23
Zn1	0.0359 (2)	0.0264 (2)	0.0302 (2)	0.01204 (16)	0.01047 (15)	0.00882 (14)
O1	0.0418 (12)	0.0331 (11)	0.0389 (12)	0.0145 (10)	0.0196 (10)	0.0115 (9)
O2	0.0562 (14)	0.0343 (12)	0.0543 (14)	0.0227 (11)	0.0270 (12)	0.0103 (10)
O3	0.0583 (15)	0.0309 (12)	0.0426 (13)	0.0103 (11)	0.0167 (11)	0.0174 (10)
O4	0.0445 (14)	0.0400 (14)	0.0877 (18)	0.0156 (11)	0.0265 (13)	0.0285 (13)
N1	0.0354 (14)	0.0328 (14)	0.0356 (14)	0.0136 (11)	0.0101 (11)	0.0127 (11)
N2	0.0378 (14)	0.0285 (13)	0.0316 (13)	0.0149 (11)	0.0062 (11)	0.0050 (11)
N6	0.0413 (15)	0.0303 (14)	0.0310 (13)	0.0149 (12)	0.0072 (12)	0.0021 (11)
N9	0.0292 (13)	0.0356 (14)	0.0442 (15)	0.0129 (11)	0.0050 (12)	0.0132 (12)
C1	0.065 (2)	0.0356 (18)	0.055 (2)	0.0290 (17)	0.0345 (18)	0.0205 (16)
C4	0.0277 (15)	0.0310 (16)	0.0322 (16)	0.0114 (13)	0.0076 (13)	0.0064 (13)
C6	0.0295 (15)	0.0303 (16)	0.0355 (16)	0.0108 (13)	0.0131 (13)	0.0099 (13)
C9	0.0442 (18)	0.0294 (16)	0.0335 (16)	0.0177 (14)	0.0108 (14)	0.0041 (13)
C10	0.047 (2)	0.0300 (17)	0.0406 (18)	0.0159 (15)	0.0230 (16)	0.0068 (14)
C11	0.054 (2)	0.0357 (18)	0.0436 (19)	0.0276 (17)	0.0028 (16)	0.0059 (15)
C13	0.0429 (18)	0.0308 (16)	0.0307 (16)	0.0170 (14)	0.0045 (14)	0.0095 (13)
C18	0.0387 (17)	0.0311 (16)	0.0396 (18)	0.0133 (14)	−0.0029 (14)	0.0138 (14)
C20	0.0467 (19)	0.0323 (16)	0.0418 (18)	0.0176 (15)	0.0227 (15)	0.0130 (14)
C22	0.090 (3)	0.050 (2)	0.0291 (19)	0.023 (2)	0.002 (2)	0.0006 (17)
C23	0.0468 (19)	0.0297 (17)	0.0389 (18)	0.0094 (15)	0.0094 (15)	0.0065 (14)
C26	0.0306 (17)	0.0350 (17)	0.052 (2)	0.0131 (14)	0.0115 (15)	0.0189 (15)
C27	0.0395 (18)	0.0410 (18)	0.0437 (18)	0.0156 (15)	0.0193 (15)	0.0142 (15)
C28	0.043 (2)	0.0381 (18)	0.053 (2)	0.0153 (16)	0.0167 (17)	0.0197 (16)
C31	0.059 (2)	0.0366 (18)	0.051 (2)	0.0241 (16)	0.0316 (17)	0.0223 (16)
C32	0.047 (2)	0.0376 (18)	0.053 (2)	0.0205 (16)	0.0159 (17)	0.0215 (16)
C33	0.0415 (19)	0.0430 (19)	0.0423 (19)	0.0166 (16)	0.0126 (16)	0.0033 (15)
C37	0.057 (2)	0.0293 (18)	0.0427 (18)	0.0209 (16)	0.0070 (17)	0.0055 (14)
C38	0.077 (3)	0.053 (2)	0.0397 (19)	0.030 (2)	0.023 (2)	0.0154 (17)
C39	0.059 (2)	0.040 (2)	0.040 (2)	0.0102 (18)	−0.0127 (18)	0.0063 (16)
C45	0.0325 (18)	0.040 (2)	0.064 (2)	0.0126 (15)	−0.0018 (17)	0.0198 (18)
C46	0.0337 (18)	0.0428 (19)	0.053 (2)	0.0159 (15)	0.0153 (15)	0.0129 (16)

Zn1—O3	1.967 (2)	C13—C33	1.515 (4)
Zn1—O1	1.9680 (19)	C18—C39	1.399 (5)
Zn1—N2	1.999 (2)	C18—C45ii	1.497 (4)
Zn1—N1	2.036 (2)	C20—C32	1.384 (4)
O1—C4	1.283 (3)	C20—C28	1.393 (4)
O2—C4	1.240 (3)	C22—C39	1.364 (5)
O3—C10	1.244 (4)	C22—C38	1.369 (5)
O4—C10	1.234 (4)	C22—H22	0.9271
N1—C26	1.310 (3)	C23—C38	1.378 (4)
N1—C27	1.370 (4)	C23—H23	0.9299
N2—C9	1.313 (4)	C26—H26	0.9298
N2—C11	1.373 (4)	C27—C46	1.347 (4)
N6—C9	1.344 (3)	C27—H27	0.9297
N6—C37	1.369 (4)	C28—C32iii	1.381 (4)
N6—C33	1.464 (4)	C28—H28	0.9299
N9—C26	1.339 (4)	C31—C1i	1.386 (4)
N9—C46	1.364 (4)	C31—H31	0.9294
N9—C45	1.478 (4)	C32—C28iii	1.381 (4)
C1—C31i	1.386 (4)	C32—H32	0.9283
C1—C6	1.387 (4)	C33—H33A	0.9696
C1—H1	0.9289	C33—H33B	0.9695
C4—C6	1.506 (4)	C37—H37	0.9299
C6—C31	1.383 (4)	C38—H38	0.9292
C9—H9	0.9291	C39—H39	0.9280
C10—C20	1.522 (4)	C45—C18ii	1.497 (4)
C11—C37	1.340 (4)	C45—H45A	0.9699
C11—H11	0.9294	C45—H45B	0.9696
C13—C23	1.383 (4)	C46—H46	0.9284
C13—C18	1.398 (4)
O3—Zn1—O1	105.82 (9)	C28—C20—C10	120.3 (3)
O3—Zn1—N2	118.54 (9)	C39—C22—C38	120.2 (3)
O1—Zn1—N2	115.65 (9)	C39—C22—H22	119.6
O3—Zn1—N1	100.79 (10)	C38—C22—H22	120.1
O1—Zn1—N1	109.17 (9)	C38—C23—C13	120.9 (3)
N2—Zn1—N1	105.62 (10)	C38—C23—H23	119.8
C4—O1—Zn1	115.41 (18)	C13—C23—H23	119.2
C10—O3—Zn1	111.8 (2)	N1—C26—N9	111.6 (3)
C26—N1—C27	105.7 (2)	N1—C26—H26	124.3
C26—N1—Zn1	125.8 (2)	N9—C26—H26	124.2
C27—N1—Zn1	128.4 (2)	C46—C27—N1	109.2 (3)
C9—N2—C11	105.6 (2)	C46—C27—H27	125.4
C9—N2—Zn1	125.44 (19)	N1—C27—H27	125.3
C11—N2—Zn1	126.0 (2)	C32iii—C28—C20	120.3 (3)
C9—N6—C37	107.5 (3)	C32iii—C28—H28	119.8
C9—N6—C33	125.4 (3)	C20—C28—H28	120.0
C37—N6—C33	126.5 (3)	C6—C31—C1i	121.5 (3)
C26—N9—C46	106.8 (3)	C6—C31—H31	119.3
C26—N9—C45	127.3 (3)	C1i—C31—H31	119.2
C46—N9—C45	125.9 (3)	C28iii—C32—C20	121.0 (3)
C31i—C1—C6	120.5 (3)	C28iii—C32—H32	119.7
C31i—C1—H1	119.6	C20—C32—H32	119.3
C6—C1—H1	119.9	N6—C33—C13	113.4 (3)
O2—C4—O1	124.7 (3)	N6—C33—H33A	108.9
O2—C4—C6	119.0 (2)	C13—C33—H33A	108.9
O1—C4—C6	116.3 (2)	N6—C33—H33B	108.8
C31—C6—C1	118.0 (3)	C13—C33—H33B	109.0
C31—C6—C4	121.4 (3)	H33A—C33—H33B	107.7
C1—C6—C4	120.6 (3)	C11—C37—N6	105.9 (3)
N2—C9—N6	110.9 (3)	C11—C37—H37	126.8
N2—C9—H9	124.7	N6—C37—H37	127.2
N6—C9—H9	124.5	C22—C38—C23	119.7 (4)
O4—C10—O3	124.9 (3)	C22—C38—H38	120.3
O4—C10—C20	118.8 (3)	C23—C38—H38	120.0
O3—C10—C20	116.2 (3)	C22—C39—C18	121.5 (3)
C37—C11—N2	110.1 (3)	C22—C39—H39	119.3
C37—C11—H11	124.9	C18—C39—H39	119.3
N2—C11—H11	125.0	N9—C45—C18ii	111.3 (3)
C23—C13—C18	119.7 (3)	N9—C45—H45A	109.3
C23—C13—C33	119.4 (3)	C18ii—C45—H45A	109.5
C18—C13—C33	120.9 (3)	N9—C45—H45B	109.4
C13—C18—C39	118.0 (3)	C18ii—C45—H45B	109.4
C13—C18—C45ii	123.6 (3)	H45A—C45—H45B	108.0
C39—C18—C45ii	118.4 (3)	C27—C46—N9	106.7 (3)
C32—C20—C28	118.8 (3)	C27—C46—H46	126.5
C32—C20—C10	120.9 (3)	N9—C46—H46	126.8