Poly[zinc(II)-[μ-1,4-bis-(imidazol-1-yl-methyl)benzene]-μ-4,4'-oxydibenzoato].

In the title compound, [Zn(C(14)H(8)O(5))(C(14)H(14)N(4))](n), the coordination polyhedron around each Zn(II) atom is a distorted tetra-hedron. The ligands bridge the Zn atoms to form a two-dimensional (4,4)-network.

Related literature

For related literature, see Batten & Robson (1998 ▶); Ma et al. (2003 ▶).

Experimental

Crystal data

[Zn(C14H8O5)(C14H14N4)]

M = 559.87

Monoclinic,

a = 6.1608 (9) Å

b = 25.811 (4) Å

c = 16.185 (3) Å

β = 92.503 (2)°

V = 2571.2 (7) Å3

Z = 4

Mo Kα radiation

μ = 1.00 mm−1

T = 293 (2) K

0.33 × 0.25 × 0.19 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.718, T max = 0.826

14194 measured reflections

5057 independent reflections

3906 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.159

S = 1.07

5057 reflections

343 parameters

H-atom parameters constrained

Δρmax = 1.43 e Å−3

Δρmin = −0.31 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 global, I. DOI: 10.1107/S1600536808023982/bt2755sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023982/bt2755Isup2.hkl

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

[Zn(C14H8O5)(C14H14N4)]	F000 = 1152
Mr = 559.87	Dx = 1.446 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5057 reflections
a = 6.1608 (9) Å	θ = 1.9–26.1º
b = 25.811 (4) Å	µ = 1.00 mm−1
c = 16.185 (3) Å	T = 293 (2) K
β = 92.503 (2)º	Block, colourless
V = 2571.2 (7) Å3	0.33 × 0.25 × 0.19 mm
Z = 4

Bruker APEX CCD area-detector diffractometer	5057 independent reflections
Radiation source: fine-focus sealed tube	3906 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.047
T = 293(2) K	θmax = 26.1º
φ and ω scans	θmin = 1.5º
Absorption correction: multi-scan(SADABS; Bruker, 1998)	h = −7→6
Tmin = 0.718, Tmax = 0.826	k = −31→27
14194 measured reflections	l = −19→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061	H-atom parameters constrained
wR(F2) = 0.159	w = 1/[σ2(Fo2) + (0.0761P)2 + 2.2361P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
5057 reflections	Δρmax = 1.43 e Å−3
343 parameters	Δρmin = −0.31 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
C1	0.1661 (7)	0.04984 (15)	0.0495 (3)	0.0273 (9)
H1	0.0525	0.0275	0.0603	0.033*
C2	0.3029 (7)	0.04487 (16)	−0.0136 (3)	0.0284 (9)
H2	0.3004	0.0190	−0.0537	0.034*
C3	0.3919 (7)	0.11368 (15)	0.0599 (3)	0.0281 (9)
H3	0.4643	0.1434	0.0784	0.034*
C4	0.6352 (8)	0.09401 (17)	−0.0563 (3)	0.0384 (11)
H4A	0.6121	0.0764	−0.1089	0.046*
H4B	0.7623	0.0789	−0.0283	0.046*
C5	0.6768 (7)	0.15040 (16)	−0.0719 (3)	0.0312 (10)
C6	0.5194 (8)	0.18139 (19)	−0.1091 (3)	0.0416 (12)
H6	0.3861	0.1668	−0.1251	0.050*
C7	0.5531 (8)	0.23363 (19)	−0.1233 (3)	0.0440 (12)
H7	0.4425	0.2537	−0.1476	0.053*
C8	0.7516 (7)	0.25584 (16)	−0.1014 (3)	0.0274 (9)
C9	0.9128 (7)	0.22467 (18)	−0.0648 (3)	0.0355 (11)
H9	1.0479	0.2388	−0.0502	0.043*
C10	0.8738 (8)	0.17265 (18)	−0.0500 (3)	0.0379 (11)
H10	0.9828	0.1524	−0.0249	0.045*
C11	0.8036 (7)	0.31222 (17)	−0.1168 (3)	0.0333 (10)
H11A	0.8759	0.3266	−0.0675	0.040*
H11B	0.9032	0.3145	−0.1614	0.040*
C12	0.4828 (8)	0.36811 (18)	−0.0836 (3)	0.0393 (12)
H12	0.5095	0.3720	−0.0269	0.047*
C13	0.3094 (8)	0.38615 (17)	−0.1294 (3)	0.0349 (11)
H13	0.1968	0.4057	−0.1091	0.042*
C14	0.5102 (7)	0.34527 (16)	−0.2128 (3)	0.0272 (9)
H14	0.5639	0.3306	−0.2603	0.033*
C15	−0.2311 (7)	0.04825 (15)	0.2220 (3)	0.0269 (9)
C16	−0.3735 (7)	0.01450 (15)	0.2723 (3)	0.0272 (9)
C17	−0.5687 (7)	−0.00464 (16)	0.2373 (3)	0.0312 (10)
H17	−0.6076	0.0032	0.1826	0.037*
C18	−0.7053 (7)	−0.03508 (17)	0.2825 (3)	0.0332 (10)
H18	−0.8353	−0.0475	0.2587	0.040*
C19	−0.6446 (7)	−0.04668 (15)	0.3635 (3)	0.0301 (10)
C20	−0.4550 (8)	−0.02835 (16)	0.4000 (3)	0.0322 (10)
H20	−0.4174	−0.0366	0.4547	0.039*
C21	−0.3190 (7)	0.00262 (16)	0.3547 (3)	0.0305 (10)
H21	−0.1910	0.0155	0.3795	0.037*
C22	−0.8501 (7)	−0.12400 (15)	0.3885 (3)	0.0291 (9)
C23	−0.7128 (7)	−0.15793 (17)	0.3502 (3)	0.0370 (11)
H23	−0.5768	−0.1471	0.3344	0.044*
C24	−0.7814 (7)	−0.20848 (16)	0.3356 (3)	0.0350 (11)
H24	−0.6888	−0.2318	0.3111	0.042*
C25	−0.9857 (7)	−0.22472 (15)	0.3571 (3)	0.0268 (9)
C26	−1.0669 (7)	−0.27912 (16)	0.3427 (3)	0.0294 (10)
C27	−1.1208 (7)	−0.18936 (16)	0.3946 (3)	0.0333 (10)
H27	−1.2587	−0.1997	0.4090	0.040*
C28	−1.0534 (7)	−0.13930 (17)	0.4106 (3)	0.0340 (10)
H28	−1.1446	−0.1161	0.4360	0.041*
N1	0.2223 (6)	0.09330 (12)	0.0948 (2)	0.0258 (8)
N2	0.4459 (6)	0.08575 (13)	−0.0061 (2)	0.0270 (8)
N3	0.6107 (6)	0.34292 (13)	−0.1381 (2)	0.0281 (8)
N4	0.3250 (6)	0.37110 (13)	−0.2109 (2)	0.0282 (8)
O1	−0.0854 (5)	0.07421 (11)	0.26198 (18)	0.0326 (7)
O2	−0.2634 (5)	0.05027 (12)	0.14567 (18)	0.0353 (7)
O3	−1.2588 (5)	−0.28926 (12)	0.3550 (2)	0.0393 (8)
O4	−0.9314 (5)	−0.31274 (11)	0.31674 (19)	0.0331 (7)
O5	−0.7843 (5)	−0.07438 (11)	0.41306 (19)	0.0380 (8)
Zn1	0.09373 (8)	0.120902 (17)	0.19746 (3)	0.02586 (17)

	U11	U22	U33	U12	U13	U23
C1	0.028 (2)	0.022 (2)	0.032 (2)	−0.0029 (17)	−0.0013 (18)	−0.0012 (17)
C2	0.030 (2)	0.026 (2)	0.029 (2)	0.0022 (18)	−0.0012 (18)	−0.0039 (17)
C3	0.032 (2)	0.020 (2)	0.032 (2)	0.0034 (17)	0.0039 (19)	−0.0014 (17)
C4	0.039 (3)	0.028 (2)	0.049 (3)	0.004 (2)	0.023 (2)	0.004 (2)
C5	0.036 (3)	0.029 (2)	0.030 (2)	0.0011 (19)	0.011 (2)	0.0031 (18)
C6	0.030 (3)	0.042 (3)	0.052 (3)	−0.008 (2)	−0.004 (2)	0.011 (2)
C7	0.032 (3)	0.040 (3)	0.059 (3)	−0.003 (2)	−0.005 (2)	0.021 (2)
C8	0.026 (2)	0.031 (2)	0.026 (2)	0.0028 (18)	0.0033 (17)	0.0044 (17)
C9	0.025 (2)	0.038 (3)	0.044 (3)	0.001 (2)	−0.003 (2)	0.001 (2)
C10	0.032 (3)	0.035 (3)	0.047 (3)	0.008 (2)	−0.001 (2)	0.008 (2)
C11	0.024 (2)	0.037 (3)	0.038 (3)	−0.0009 (19)	−0.0014 (19)	0.005 (2)
C12	0.052 (3)	0.035 (3)	0.031 (2)	0.001 (2)	0.003 (2)	−0.003 (2)
C13	0.040 (3)	0.029 (2)	0.036 (3)	0.003 (2)	0.010 (2)	−0.0047 (19)
C14	0.026 (2)	0.029 (2)	0.027 (2)	0.0018 (18)	0.0003 (18)	0.0035 (17)
C15	0.027 (2)	0.017 (2)	0.037 (3)	0.0043 (17)	0.0066 (19)	0.0005 (17)
C16	0.032 (2)	0.018 (2)	0.033 (2)	0.0043 (17)	0.0065 (19)	−0.0012 (17)
C17	0.040 (3)	0.026 (2)	0.028 (2)	−0.0034 (19)	0.000 (2)	0.0000 (18)
C18	0.030 (3)	0.032 (2)	0.037 (3)	−0.009 (2)	−0.001 (2)	−0.0031 (19)
C19	0.040 (3)	0.016 (2)	0.034 (2)	−0.0043 (18)	0.009 (2)	−0.0005 (17)
C20	0.048 (3)	0.024 (2)	0.025 (2)	−0.001 (2)	0.003 (2)	0.0018 (17)
C21	0.032 (2)	0.025 (2)	0.033 (2)	−0.0044 (18)	−0.0035 (19)	−0.0005 (18)
C22	0.041 (3)	0.021 (2)	0.026 (2)	−0.0033 (19)	0.0050 (19)	0.0005 (17)
C23	0.031 (3)	0.033 (2)	0.048 (3)	−0.011 (2)	0.013 (2)	0.000 (2)
C24	0.035 (3)	0.024 (2)	0.047 (3)	0.0005 (19)	0.019 (2)	−0.0029 (19)
C25	0.028 (2)	0.022 (2)	0.031 (2)	−0.0032 (17)	0.0027 (18)	0.0014 (17)
C26	0.035 (3)	0.021 (2)	0.032 (2)	−0.0009 (18)	0.0055 (19)	0.0008 (17)
C27	0.030 (2)	0.027 (2)	0.043 (3)	−0.0020 (19)	0.009 (2)	−0.0003 (19)
C28	0.036 (3)	0.025 (2)	0.042 (3)	0.0024 (19)	0.013 (2)	−0.0013 (19)
N1	0.030 (2)	0.0206 (17)	0.0268 (18)	0.0008 (15)	0.0026 (15)	−0.0004 (14)
N2	0.029 (2)	0.0230 (18)	0.0299 (18)	0.0035 (15)	0.0051 (15)	0.0005 (14)
N3	0.029 (2)	0.0268 (19)	0.0286 (19)	−0.0002 (15)	0.0015 (16)	0.0065 (15)
N4	0.030 (2)	0.0240 (18)	0.0303 (19)	0.0032 (15)	0.0033 (15)	0.0039 (15)
O1	0.0351 (18)	0.0278 (16)	0.0354 (17)	−0.0094 (13)	0.0073 (14)	0.0003 (13)
O2	0.0397 (19)	0.0369 (18)	0.0300 (17)	−0.0037 (14)	0.0068 (14)	0.0024 (13)
O3	0.0345 (19)	0.0294 (17)	0.055 (2)	−0.0072 (14)	0.0087 (16)	−0.0032 (15)
O4	0.0340 (18)	0.0234 (15)	0.0426 (18)	−0.0012 (13)	0.0088 (14)	−0.0021 (13)
O5	0.053 (2)	0.0251 (16)	0.0375 (18)	−0.0140 (14)	0.0200 (16)	−0.0062 (13)
Zn1	0.0284 (3)	0.0203 (3)	0.0292 (3)	−0.0010 (2)	0.0048 (2)	−0.00183 (19)

C1—C2	1.357 (6)	C15—O2	1.243 (5)
C1—N1	1.376 (5)	C15—O1	1.274 (5)
C1—H1	0.9300	C15—C16	1.502 (6)
C2—N2	1.377 (5)	C16—C21	1.395 (6)
C2—H2	0.9300	C16—C17	1.397 (6)
C3—N1	1.319 (5)	C17—C18	1.383 (6)
C3—N2	1.342 (5)	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.381 (6)
C4—N2	1.466 (5)	C18—H18	0.9300
C4—C5	1.501 (6)	C19—C20	1.370 (6)
C4—H4A	0.9700	C19—O5	1.398 (5)
C4—H4B	0.9700	C20—C21	1.389 (6)
C5—C6	1.375 (6)	C20—H20	0.9300
C5—C10	1.375 (6)	C21—H21	0.9300
C6—C7	1.385 (6)	C22—C28	1.375 (6)
C6—H6	0.9300	C22—C23	1.383 (6)
C7—C8	1.383 (6)	C22—O5	1.396 (5)
C7—H7	0.9300	C23—C24	1.389 (6)
C8—C9	1.390 (6)	C23—H23	0.9300
C8—C11	1.513 (6)	C24—C25	1.385 (6)
C9—C10	1.387 (6)	C24—H24	0.9300
C9—H9	0.9300	C25—C27	1.392 (6)
C10—H10	0.9300	C25—C26	1.505 (6)
C11—N3	1.457 (5)	C26—O3	1.236 (5)
C11—H11A	0.9700	C26—O4	1.288 (5)
C11—H11B	0.9700	C27—C28	1.378 (6)
C12—C13	1.356 (7)	C27—H27	0.9300
C12—N3	1.372 (6)	C28—H28	0.9300
C12—H12	0.9300	N1—Zn1	2.002 (3)
C13—N4	1.383 (5)	N4—Zn1i	2.021 (4)
C13—H13	0.9300	O1—Zn1	1.965 (3)
C14—N4	1.323 (5)	O4—Zn1ii	1.992 (3)
C14—N3	1.336 (5)	Zn1—O4iii	1.992 (3)
C14—H14	0.9300	Zn1—N4iv	2.021 (4)
C2—C1—N1	109.1 (4)	C16—C17—H17	119.3
C2—C1—H1	125.4	C19—C18—C17	118.6 (4)
N1—C1—H1	125.4	C19—C18—H18	120.7
C1—C2—N2	106.1 (4)	C17—C18—H18	120.7
C1—C2—H2	126.9	C20—C19—C18	121.6 (4)
N2—C2—H2	126.9	C20—C19—O5	117.7 (4)
N1—C3—N2	110.8 (4)	C18—C19—O5	120.5 (4)
N1—C3—H3	124.6	C19—C20—C21	119.6 (4)
N2—C3—H3	124.6	C19—C20—H20	120.2
N2—C4—C5	112.3 (3)	C21—C20—H20	120.2
N2—C4—H4A	109.1	C20—C21—C16	120.3 (4)
C5—C4—H4A	109.1	C20—C21—H21	119.8
N2—C4—H4B	109.1	C16—C21—H21	119.8
C5—C4—H4B	109.1	C28—C22—C23	121.1 (4)
H4A—C4—H4B	107.9	C28—C22—O5	116.5 (4)
C6—C5—C10	117.9 (4)	C23—C22—O5	122.2 (4)
C6—C5—C4	121.0 (4)	C22—C23—C24	118.9 (4)
C10—C5—C4	121.1 (4)	C22—C23—H23	120.5
C5—C6—C7	122.1 (4)	C24—C23—H23	120.5
C5—C6—H6	119.0	C25—C24—C23	121.0 (4)
C7—C6—H6	119.0	C25—C24—H24	119.5
C8—C7—C6	119.9 (4)	C23—C24—H24	119.5
C8—C7—H7	120.1	C24—C25—C27	118.6 (4)
C6—C7—H7	120.1	C24—C25—C26	122.9 (4)
C7—C8—C9	118.5 (4)	C27—C25—C26	118.5 (4)
C7—C8—C11	123.2 (4)	O3—C26—O4	123.3 (4)
C9—C8—C11	118.3 (4)	O3—C26—C25	119.1 (4)
C10—C9—C8	120.5 (4)	O4—C26—C25	117.6 (4)
C10—C9—H9	119.7	C28—C27—C25	121.0 (4)
C8—C9—H9	119.7	C28—C27—H27	119.5
C5—C10—C9	121.2 (4)	C25—C27—H27	119.5
C5—C10—H10	119.4	C22—C28—C27	119.4 (4)
C9—C10—H10	119.4	C22—C28—H28	120.3
N3—C11—C8	112.7 (4)	C27—C28—H28	120.3
N3—C11—H11A	109.1	C3—N1—C1	106.4 (3)
C8—C11—H11A	109.1	C3—N1—Zn1	124.3 (3)
N3—C11—H11B	109.1	C1—N1—Zn1	129.2 (3)
C8—C11—H11B	109.1	C3—N2—C2	107.5 (3)
H11A—C11—H11B	107.8	C3—N2—C4	126.4 (4)
C13—C12—N3	105.8 (4)	C2—N2—C4	125.8 (4)
C13—C12—H12	127.1	C14—N3—C12	107.7 (4)
N3—C12—H12	127.1	C14—N3—C11	125.4 (4)
C12—C13—N4	109.9 (4)	C12—N3—C11	126.2 (4)
C12—C13—H13	125.1	C14—N4—C13	105.0 (4)
N4—C13—H13	125.1	C14—N4—Zn1i	128.0 (3)
N4—C14—N3	111.6 (4)	C13—N4—Zn1i	126.5 (3)
N4—C14—H14	124.2	C15—O1—Zn1	116.9 (3)
N3—C14—H14	124.2	C26—O4—Zn1ii	106.7 (3)
O2—C15—O1	124.1 (4)	C22—O5—C19	119.0 (3)
O2—C15—C16	119.5 (4)	O1—Zn1—O4iii	107.32 (12)
O1—C15—C16	116.4 (4)	O1—Zn1—N1	118.32 (13)
C21—C16—C17	118.5 (4)	O4iii—Zn1—N1	115.16 (13)
C21—C16—C15	121.6 (4)	O1—Zn1—N4iv	93.85 (13)
C17—C16—C15	119.9 (4)	O4iii—Zn1—N4iv	109.34 (13)
C18—C17—C16	121.3 (4)	N1—Zn1—N4iv	110.68 (14)
C18—C17—H17	119.3