catena-Poly[zinc(II)-bis­[μ₂-3-(3-pyrid­yl)­benzoato]-κ² O:N;κ² N:O]

Abstract

In the title compound, [Zn(C₁₂H₈NO₂)₂]_n, the Zn²⁺ cation is coordinated by a pair of carboxyl­ate O atoms as well as two pyridyl N atoms to afford a distorted tetra­hedral environment. Adjacent Zn²⁺ cations, with a separation of 8.807 (2) Å, are linked by two 3-(3-pyrid­yl)benzoate ligand bridges, generating an infinite ribbon extending parallel to [001].

Related literature

For the use of 3-(pyridin-3-yl)benzoate units in the construction of framework structures, see: Guo (2009 ▶). For a similar structure, see: Zhong et al. (2008 ▶).

Experimental

Crystal data

• [Zn(C₁₂H₈NO₂)₂]

• M _r = 461.76

• Monoclinic,

• a = 10.0512 (8) Å

• b = 12.0809 (10) Å

• c = 17.4872 (14) Å

• β = 105.631 (1)°

• V = 2044.9 (3) ų

• Z = 4

• Mo Kα radiation

• μ = 1.24 mm⁻¹

• T = 273 K

• 0.15 × 0.10 × 0.08 mm

Data collection

• Bruker SMART CCD diffractometer

• Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.836, T _max = 0.908

• 10620 measured reflections

• 3616 independent reflections

• 2253 reflections with I > 2σ(I)

• R _int = 0.050

Refinement

• R[F ² > 2σ(F ²)] = 0.042

• wR(F ²) = 0.095

• S = 1.08

• 3616 reflections

• 280 parameters

• H-atom parameters constrained

• Δρ_max = 0.26 e Å⁻³

• Δρ_min = −0.29 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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.

Supplementary Material

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

supplementary crystallographic information

Comment

In the structure of the title compound, the Zn²⁺ center is located at the general site and coordinated by a pair of carboxylate oxygen atoms as well as two pyridyl nitrogen donors to afford a tetrahedral environment (see Fig. 1). As a result, the Zn²⁺ ions are connected by the 3-(pyridin-3-yl)benzoate spacers to result in a in?nite 1D double-strand chain motif, with the Zn···Zn separation of 8.807Å, as shown in Fig. 2.

Experimental

The title compound was prepared by hydrothermal method. An aqueous solution (20 mL) containing 3-(pyridin-3-yl)benzoate acid (0.10 mmol) and Zinc nitrate hexahydrate (0.10 mmol) was placed in a Parr Te?on-lined stainless steel vessel (25 mL) under autogenous pressure, which was heated to 433 K for 72 h and subsequently cooled to room temperature at a rate of 5 K an hour. Colorless single crystals were obtained from the reaction mixture (yield ca 46% based on Zn).

Refinement

The C-bound H atoms were geometrically placed (C—H = 0.93 Å) and refined as riding with U_iso(H) =1.2U_eq(C).

Figures

Fig. 1.

Thermal ellipsoid plot of the title compound at the 30% probability level, hydrogen atoms are drawn as sphere of arbitrary radius.

Fig. 2.

The 1D chain of the title compound, viewed down the c axis.

Crystal data

[Zn(C12H8NO2)2]	F(000) = 944
Mr = 461.76	Dx = 1.500 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.0512 (8) Å	Cell parameters from 1527 reflections
b = 12.0809 (10) Å	θ = 2.4–21.1°
c = 17.4872 (14) Å	µ = 1.24 mm−1
β = 105.631 (1)°	T = 273 K
V = 2044.9 (3) Å3	Block, colourless
Z = 4	0.15 × 0.10 × 0.08 mm

Data collection

Bruker SMART diffractometer	3616 independent reflections
Radiation source: fine-focus sealed tube	2253 reflections with I > 2σ(I)
graphite	Rint = 0.050
φ and ω scans	θmax = 25.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→11
Tmin = 0.836, Tmax = 0.908	k = −14→14
10620 measured reflections	l = −20→20

Refinement

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) = 0.095	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0353P)2] where P = (Fo2 + 2Fc2)/3
3616 reflections	(Δ/σ)max = 0.001
280 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Zn1	0.54736 (4)	0.79354 (4)	0.82510 (2)	0.04985 (17)
C1	0.4220 (4)	0.6225 (3)	0.8717 (2)	0.0479 (9)
C2	0.3496 (3)	0.5541 (3)	0.92062 (18)	0.0401 (9)
C3	0.2852 (4)	0.4556 (3)	0.8909 (2)	0.0478 (10)
H3	0.2882	0.4309	0.8410	0.057*
C4	0.2170 (4)	0.3943 (3)	0.9347 (2)	0.0525 (10)
H4	0.1750	0.3279	0.9146	0.063*
C5	0.2105 (4)	0.4308 (3)	1.0087 (2)	0.0473 (9)
H5	0.1635	0.3893	1.0379	0.057*
C6	0.2743 (3)	0.5295 (3)	1.03928 (18)	0.0389 (9)
C7	0.3441 (3)	0.5902 (3)	0.99507 (18)	0.0415 (9)
H7	0.3879	0.6558	1.0155	0.050*
C8	0.2645 (4)	0.5697 (3)	1.11789 (18)	0.0379 (8)
C9	0.3784 (4)	0.6111 (3)	1.17361 (18)	0.0415 (9)
H9	0.4620	0.6142	1.1604	0.050*
C10	0.2537 (4)	0.6462 (3)	1.2631 (2)	0.0519 (10)
H10	0.2495	0.6732	1.3123	0.062*
C11	0.1359 (4)	0.6076 (3)	1.2119 (2)	0.0556 (11)
H11	0.0529	0.6080	1.2259	0.067*
C12	0.1416 (4)	0.5679 (3)	1.1389 (2)	0.0512 (10)
H12	0.0624	0.5397	1.1037	0.061*
C13	0.7782 (4)	0.7247 (3)	0.7844 (2)	0.0525 (10)
C14	0.8517 (4)	0.6655 (3)	0.73188 (19)	0.0444 (9)
C15	0.7794 (4)	0.6278 (3)	0.65703 (19)	0.0449 (9)
H15	0.6856	0.6430	0.6380	0.054*
C16	0.8458 (4)	0.5675 (3)	0.6104 (2)	0.0474 (10)
C17	0.9861 (4)	0.5446 (3)	0.6400 (2)	0.0607 (11)
H17	1.0310	0.5021	0.6102	0.073*
C18	1.0589 (4)	0.5845 (3)	0.7132 (2)	0.0664 (12)
H18	1.1535	0.5719	0.7317	0.080*
C19	0.9909 (4)	0.6432 (3)	0.7588 (2)	0.0553 (10)
H19	1.0400	0.6683	0.8087	0.066*
C20	0.7694 (4)	0.5294 (3)	0.52977 (19)	0.0475 (9)
C21	0.6937 (4)	0.6032 (3)	0.47544 (19)	0.0494 (10)
H21	0.6875	0.6758	0.4918	0.059*
C22	0.6343 (4)	0.4723 (4)	0.3773 (2)	0.0625 (12)
H22	0.5881	0.4524	0.3256	0.075*
C23	0.7069 (5)	0.3932 (4)	0.4277 (3)	0.0826 (15)
H23	0.7096	0.3207	0.4102	0.099*
C24	0.7762 (5)	0.4218 (4)	0.5045 (2)	0.0742 (13)
H24	0.8270	0.3691	0.5390	0.089*
N1	0.3752 (3)	0.6471 (2)	1.24571 (15)	0.0437 (7)
N2	0.6278 (3)	0.5766 (3)	0.39999 (16)	0.0497 (8)
O1	0.4801 (2)	0.7115 (2)	0.90317 (13)	0.0540 (7)
O2	0.4192 (3)	0.5923 (2)	0.80425 (14)	0.0648 (8)
O3	0.6515 (3)	0.7467 (2)	0.75352 (14)	0.0635 (8)
O4	0.8408 (3)	0.7481 (3)	0.85317 (16)	0.0880 (10)

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Zn1	0.0573 (3)	0.0665 (3)	0.0242 (2)	0.0047 (2)	0.00805 (19)	0.0020 (2)
C1	0.050 (2)	0.059 (3)	0.031 (2)	0.013 (2)	0.0045 (18)	0.0057 (19)
C2	0.043 (2)	0.047 (2)	0.0264 (18)	0.0099 (18)	0.0020 (16)	0.0005 (16)
C3	0.054 (3)	0.052 (3)	0.032 (2)	0.013 (2)	0.0025 (18)	−0.0080 (18)
C4	0.057 (3)	0.051 (3)	0.044 (2)	0.000 (2)	0.004 (2)	−0.0111 (19)
C5	0.047 (2)	0.053 (3)	0.039 (2)	−0.0027 (19)	0.0055 (17)	−0.0026 (18)
C6	0.038 (2)	0.046 (2)	0.0277 (19)	0.0053 (18)	0.0002 (16)	−0.0003 (16)
C7	0.046 (2)	0.045 (2)	0.0298 (19)	0.0021 (17)	0.0026 (17)	−0.0033 (16)
C8	0.040 (2)	0.044 (2)	0.0280 (18)	0.0017 (17)	0.0063 (16)	0.0005 (15)
C9	0.041 (2)	0.052 (2)	0.031 (2)	0.0046 (18)	0.0090 (16)	0.0023 (16)
C10	0.062 (3)	0.057 (3)	0.040 (2)	−0.008 (2)	0.021 (2)	−0.0050 (19)
C11	0.053 (3)	0.067 (3)	0.055 (3)	−0.008 (2)	0.028 (2)	−0.013 (2)
C12	0.049 (3)	0.056 (3)	0.047 (2)	−0.008 (2)	0.0096 (19)	−0.0052 (19)
C13	0.068 (3)	0.056 (3)	0.033 (2)	0.005 (2)	0.014 (2)	0.0092 (18)
C14	0.051 (3)	0.052 (2)	0.0290 (19)	0.0014 (19)	0.0089 (18)	0.0098 (16)
C15	0.049 (2)	0.052 (2)	0.031 (2)	0.0046 (19)	0.0079 (17)	0.0097 (17)
C16	0.059 (3)	0.052 (2)	0.034 (2)	0.004 (2)	0.0172 (19)	0.0094 (17)
C17	0.062 (3)	0.080 (3)	0.043 (2)	0.019 (2)	0.018 (2)	0.005 (2)
C18	0.051 (3)	0.095 (4)	0.053 (3)	0.012 (2)	0.013 (2)	0.010 (2)
C19	0.058 (3)	0.070 (3)	0.035 (2)	−0.003 (2)	0.007 (2)	0.005 (2)
C20	0.064 (3)	0.047 (3)	0.033 (2)	0.005 (2)	0.0150 (18)	0.0004 (18)
C21	0.064 (3)	0.050 (2)	0.032 (2)	−0.003 (2)	0.0087 (18)	−0.0055 (17)
C22	0.094 (3)	0.062 (3)	0.035 (2)	−0.015 (3)	0.024 (2)	−0.011 (2)
C23	0.142 (5)	0.050 (3)	0.057 (3)	−0.003 (3)	0.029 (3)	−0.007 (2)
C24	0.123 (4)	0.058 (3)	0.044 (3)	0.018 (3)	0.026 (3)	0.010 (2)
N1	0.049 (2)	0.055 (2)	0.0286 (16)	−0.0032 (15)	0.0128 (14)	−0.0033 (14)
N2	0.061 (2)	0.056 (2)	0.0307 (17)	−0.0053 (16)	0.0102 (15)	−0.0023 (15)
O1	0.0694 (18)	0.0601 (18)	0.0311 (13)	−0.0095 (15)	0.0109 (12)	−0.0004 (12)
O2	0.088 (2)	0.078 (2)	0.0307 (15)	0.0024 (15)	0.0201 (14)	−0.0066 (13)
O3	0.0587 (19)	0.092 (2)	0.0411 (16)	0.0112 (16)	0.0162 (14)	−0.0029 (14)
O4	0.100 (2)	0.121 (3)	0.0370 (17)	0.028 (2)	0.0069 (16)	−0.0116 (17)

Geometric parameters (Å, °)

Zn1—O3	1.921 (2)	C12—H12	0.9300
Zn1—O1	1.949 (2)	C13—O4	1.230 (4)
Zn1—N1i	2.035 (3)	C13—O3	1.270 (4)
Zn1—N2ii	2.064 (3)	C13—C14	1.506 (5)
C1—O2	1.227 (4)	C14—C19	1.377 (5)
C1—O1	1.276 (4)	C14—C15	1.392 (4)
C1—C2	1.510 (5)	C15—C16	1.391 (5)
C2—C3	1.387 (5)	C15—H15	0.9300
C2—C7	1.388 (4)	C16—C17	1.393 (5)
C3—C4	1.374 (5)	C16—C20	1.485 (5)
C3—H3	0.9300	C17—C18	1.380 (5)
C4—C5	1.385 (4)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.379 (5)
C5—C6	1.391 (4)	C18—H18	0.9300
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.385 (4)	C20—C21	1.373 (5)
C6—C8	1.486 (4)	C20—C24	1.380 (5)
C7—H7	0.9300	C21—N2	1.346 (4)
C8—C12	1.380 (4)	C21—H21	0.9300
C8—C9	1.382 (4)	C22—N2	1.327 (4)
C9—N1	1.343 (4)	C22—C23	1.370 (5)
C9—H9	0.9300	C22—H22	0.9300
C10—N1	1.335 (4)	C23—C24	1.381 (5)
C10—C11	1.361 (5)	C23—H23	0.9300
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.380 (5)	N1—Zn1ii	2.035 (3)
C11—H11	0.9300	N2—Zn1i	2.064 (3)
O3—Zn1—O1	131.25 (11)	O4—C13—C14	120.0 (4)
O3—Zn1—N1i	99.90 (11)	O3—C13—C14	116.1 (3)
O1—Zn1—N1i	105.38 (11)	C19—C14—C15	118.8 (3)
O3—Zn1—N2ii	116.65 (12)	C19—C14—C13	120.3 (3)
O1—Zn1—N2ii	95.30 (11)	C15—C14—C13	120.8 (3)
N1i—Zn1—N2ii	106.30 (12)	C16—C15—C14	120.8 (3)
O2—C1—O1	123.7 (4)	C16—C15—H15	119.6
O2—C1—C2	119.4 (4)	C14—C15—H15	119.6
O1—C1—C2	116.8 (3)	C15—C16—C17	118.9 (3)
C3—C2—C7	119.3 (3)	C15—C16—C20	120.8 (3)
C3—C2—C1	120.3 (3)	C17—C16—C20	120.3 (3)
C7—C2—C1	120.4 (3)	C18—C17—C16	120.4 (4)
C4—C3—C2	120.4 (3)	C18—C17—H17	119.8
C4—C3—H3	119.8	C16—C17—H17	119.8
C2—C3—H3	119.8	C17—C18—C19	119.7 (4)
C3—C4—C5	120.4 (4)	C17—C18—H18	120.2
C3—C4—H4	119.8	C19—C18—H18	120.2
C5—C4—H4	119.8	C14—C19—C18	121.3 (4)
C4—C5—C6	119.9 (4)	C14—C19—H19	119.4
C4—C5—H5	120.0	C18—C19—H19	119.4
C6—C5—H5	120.0	C21—C20—C24	117.1 (3)
C7—C6—C5	119.3 (3)	C21—C20—C16	120.3 (3)
C7—C6—C8	120.9 (3)	C24—C20—C16	122.5 (3)
C5—C6—C8	119.8 (3)	N2—C21—C20	123.9 (3)
C6—C7—C2	120.7 (3)	N2—C21—H21	118.0
C6—C7—H7	119.6	C20—C21—H21	118.0
C2—C7—H7	119.6	N2—C22—C23	122.1 (4)
C12—C8—C9	116.7 (3)	N2—C22—H22	119.0
C12—C8—C6	121.9 (3)	C23—C22—H22	119.0
C9—C8—C6	121.4 (3)	C22—C23—C24	119.5 (4)
N1—C9—C8	123.6 (3)	C22—C23—H23	120.3
N1—C9—H9	118.2	C24—C23—H23	120.3
C8—C9—H9	118.2	C20—C24—C23	119.5 (4)
N1—C10—C11	122.7 (3)	C20—C24—H24	120.3
N1—C10—H10	118.7	C23—C24—H24	120.3
C11—C10—H10	118.7	C10—N1—C9	117.8 (3)
C10—C11—C12	118.8 (4)	C10—N1—Zn1ii	120.6 (2)
C10—C11—H11	120.6	C9—N1—Zn1ii	121.5 (2)
C12—C11—H11	120.6	C22—N2—C21	117.9 (3)
C11—C12—C8	120.3 (3)	C22—N2—Zn1i	125.1 (3)
C11—C12—H12	119.9	C21—N2—Zn1i	116.5 (3)
C8—C12—H12	119.9	C1—O1—Zn1	109.3 (2)
O4—C13—O3	123.9 (4)	C13—O3—Zn1	116.4 (2)

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+3/2, z+1/2.