catena-Poly[zinc(II)-bis­[μ2-3-(3-pyrid­yl)­benzoato]-κ2O:N;κ2N:O]

Tang, L.; Wu, Y.-P.; Fu, F.; Hou, X.-Y.; Wei, Q.-B.

doi:10.1107/S1600536811021404

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m894

doi:10.1107/S1600536811021404

Open

access

catena-Poly[zinc(II)-bis[μ₂-3-(3-pyridyl)benzoato]-κ²O:N;κ²N:O]

Long Tang,^a Ya-Pan Wu,^a Feng Fu,^a ^* Xiang-Yang Hou ^a and Qing-Bo Wei ^a

^aDepartment of Chemistry and Chemical Engineering, Shaanxi Key Laboratory of Chemical Reaction Engineering, Yan'an University, Yan'an, Shaanxi 716000, People's Republic of China
^*Correspondence e-mail: yadxgncl@126.com

(Received 1 June 2011; accepted 3 June 2011; online 11 June 2011)

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, P 2₁ /c
a = 10.0512 (8) Å
b = 12.0809 (10) Å
c = 17.4872 (14) Å
β = 105.631 (1)°
V = 2044.9 (3) Å³
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[F² > 2σ(F²)] = 0.042
wR(F²) = 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811021404/ng5177sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811021404/ng5177Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

For the use of 3-(pyridin-3-yl)benzoate units in the synthesis of solid-state architectures, see: Guo (2009). For a similar structure, see: Zhong et al. (2008).

Experimental top

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).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top

	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.

catena-Poly[zinc(II)-bis[µ₂-3-(3-pyridyl)benzoato]- κ²O:N;κ²N:O] top

Crystal data top

[Zn(C₁₂H₈NO₂)₂]	F(000) = 944
M_r = 461.76	D_x = 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 top

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

Refinement top

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(F_o²) + (0.0353P)²] where P = (F_o² + 2F_c²)/3
3616 reflections	(Δ/σ)_max = 0.001
280 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

[Zn(C₁₂H₈NO₂)₂]	V = 2044.9 (3) Å³
M_r = 461.76	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.0512 (8) Å	µ = 1.24 mm⁻¹
b = 12.0809 (10) Å	T = 273 K
c = 17.4872 (14) Å	0.15 × 0.10 × 0.08 mm
β = 105.631 (1)°

Data collection top

Bruker SMART diffractometer	3616 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2253 reflections with I > 2σ(I)
T_min = 0.836, T_max = 0.908	R_int = 0.050
10620 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 1.08	Δρ_max = 0.26 e Å⁻³
3616 reflections	Δρ_min = −0.29 e Å⁻³
280 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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.

Experimental details

Crystal data
Chemical formula	[Zn(C₁₂H₈NO₂)₂]
M_r	461.76
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	10.0512 (8), 12.0809 (10), 17.4872 (14)
β (°)	105.631 (1)
V (Å³)	2044.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.24
Crystal size (mm)	0.15 × 0.10 × 0.08

Data collection
Diffractometer	Bruker SMART diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.836, 0.908
No. of measured, independent and observed [I > 2σ(I)] reflections	10620, 3616, 2253
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.095, 1.08
No. of reflections	3616
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.29

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This project was supported by the Natural Scientific Research Foundation of Shaanxi Provincial Education Office of China (grant No. 2010 JK905).

References

Bruker (1997). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Guo, F. (2009). J. Coord. Chem. 62, 3621–3628. CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhong, R.-Q., Zou, R.-Q., Du, M., Jiang, L., Yamada, T., Maruta, G., Takeda, S. & Xu, Q. (2008). CrystEngComm, 10, 605–613. Web of Science CSD CrossRef CAS Google Scholar