Poly[[(1,10-phenanthroline-κ2N,N′)zinc]-μ-2,5-bis­(all­yloxy)terephthalato-κ2O1:O4]

Hu, R.; Hu, Y.; Zhu, Q.

doi:10.1107/S1600536811022392

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m936

doi:10.1107/S1600536811022392

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Poly[[(1,10-phenanthroline-κ²N,N′)zinc]-μ-2,5-bis(allyloxy)terephthalato-κ²O¹:O⁴]

Ruofei Hu,^a Yuanying Hu ^a and Qingzeng Zhu ^a ^*

^aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China
^*Correspondence e-mail: qzzhu521@163.com

(Received 29 May 2011; accepted 9 June 2011; online 18 June 2011)

The title compound, [Zn(C₁₄H₁₂O₆)(C₁₂H₈N₂)]_n, is a coordination polymer forming one-dimensional infinite zigzag chains along [10 $[\overline 1]$ ] by interconnection of Zn^II atoms by 2,5-bis(allyloxy)terephthalate anions via the carboxylate groups. The Zn^II atom is located on a twofold axis and is in a distorted tetrahedral coordination formed by the two carboxylate O atoms [Zn—O = 1.9647 (12) Å] and two phenanthroline N atoms [Zn—N = 2.0949 (14) Å].

Related literature

Some other low-dimensional Zn^II complexes based on different organic carboxylic acids are described by Zhou et al. (2009 ). For the preparation of 2,5-bis(allyloxy)terephthalic acid, see: Kenichiro et al. (1998 ).

Experimental

Crystal data

[Zn(C₁₄H₁₂O₆)(C₁₂H₈N₂)]
M_r = 521.81
Monoclinic, C 2/c
a = 21.428 (10) Å
b = 9.458 (4) Å
c = 12.897 (6) Å
β = 118.462 (5)°
V = 2297.9 (18) Å³
Z = 4
Mo Kα radiation
μ = 1.12 mm⁻¹
T = 293 K
0.25 × 0.23 × 0.22 mm

Data collection

Bruker P4 diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.768, T_max = 0.792
8294 measured reflections
2546 independent reflections
2325 reflections with I > 2σ(I)
R_int = 0.028
Standard reflections: 0

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.078
S = 1.04
2546 reflections
159 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; 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 global, I. DOI: 10.1107/S1600536811022392/vn2012sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811022392/vn2012Isup2.hkl

checkCIF report

Related literature top

Some other low-dimensional Zn^II complexes based on different organic carboxylic acids are described by Zhou et al. (2009). For the preparation of 2,5-bis(allyloxy)terephthalic acid, see: Kenichiro et al. (1998).

Experimental top

2,5-Bis(allyloxy)terephthalic acid was prepared according to the literature (Kenichiro et al., 1998). Other chemicals were used as purchased. Zn(NO₃)₂6(H₂O) (8.9 mg, 0.03 mmol), 1,10-phenanthroline (1.98 mg, 0.01 mmol) and 2 ,5-bis(allyloxy)terephthalic acid (2.48 mg, 0.01 mmol) were added to the 15 ml N, N-dimethylacetamide. After stirring at room temperature for 1 h, the solution was kept at 140 °C for 3 days. Crystallization yielded pink crystals suitable for X-ray diffraction analysis (yield 2.25 mg, 39%).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); 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. Atom numbering scheme for the title compound with displacement ellipsoids shown at the 30% probability level. [symmetry codes: A, 2 - x, y, 1.5 - z; B, 1.5 - x, 0.5 - y,1 - z; C, 1/2 + x, 0.5 - y, 1/2 + z]

Poly[[(1,10-phenanthroline-κ²N,N')zinc]-µ-2,5- bis(allyloxy)terephthalato-κ²O¹:O⁴] top

Crystal data top

[Zn(C₁₄H₁₂O₆)(C₁₂H₈N₂)]	F(000) = 1072
M_r = 521.81	D_x = 1.508 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 80 reflections
a = 21.428 (10) Å	θ = 2.4–27.2°
b = 9.458 (4) Å	µ = 1.12 mm⁻¹
c = 12.897 (6) Å	T = 293 K
β = 118.462 (5)°	Block, pink
V = 2297.9 (18) Å³	0.25 × 0.23 × 0.22 mm
Z = 4

Data collection top

Bruker P4 diffractometer	2546 independent reflections
Radiation source: fine-focus sealed tube	2325 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 27.5°, θ_min = 3.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −27→27
T_min = 0.768, T_max = 0.792	k = −12→7
8294 measured reflections	l = −16→16

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0463P)² + 0.943P] where P = (F_o² + 2F_c²)/3
2546 reflections	(Δ/σ)_max = 0.001
159 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[Zn(C₁₄H₁₂O₆)(C₁₂H₈N₂)]	V = 2297.9 (18) Å³
M_r = 521.81	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 21.428 (10) Å	µ = 1.12 mm⁻¹
b = 9.458 (4) Å	T = 293 K
c = 12.897 (6) Å	0.25 × 0.23 × 0.22 mm
β = 118.462 (5)°

Data collection top

Bruker P4 diffractometer	2546 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2325 reflections with I > 2σ(I)
T_min = 0.768, T_max = 0.792	R_int = 0.028
8294 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.078	H-atom parameters constrained
S = 1.04	Δρ_max = 0.32 e Å⁻³
2546 reflections	Δρ_min = −0.34 e Å⁻³
159 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn1	1.0000	0.52903 (2)	0.7500	0.02792 (10)
O1	0.89786 (8)	0.40767 (17)	0.77262 (12)	0.0557 (4)
O2	0.91910 (6)	0.43004 (14)	0.62292 (11)	0.0391 (3)
O3	0.80413 (7)	0.19659 (16)	0.73891 (11)	0.0514 (4)
N1	0.97095 (7)	0.69874 (13)	0.82237 (11)	0.0301 (3)
C1	0.88075 (8)	0.38949 (16)	0.66788 (14)	0.0336 (3)
C2	0.81280 (8)	0.31540 (16)	0.58400 (14)	0.0312 (3)
C3	0.77669 (8)	0.22152 (18)	0.62095 (14)	0.0337 (3)
C4	0.78541 (8)	0.34259 (17)	0.46410 (15)	0.0345 (3)
H4	0.8092	0.4055	0.4398	0.041*
C5	0.76293 (11)	0.1225 (3)	0.78059 (18)	0.0574 (5)
H5A	0.7644	0.0218	0.7674	0.069*
H5B	0.7139	0.1533	0.7381	0.069*
C6	0.79184 (12)	0.1506 (3)	0.90851 (19)	0.0650 (6)
H6	0.7738	0.0967	0.9484	0.078*
C7	0.83955 (14)	0.2426 (3)	0.9693 (2)	0.0753 (7)
H7A	0.8592	0.2989	0.9331	0.090*
H7B	0.8545	0.2528	1.0494	0.090*
C8	0.94114 (9)	0.6966 (2)	0.89252 (16)	0.0409 (4)
H8	0.9341	0.6100	0.9195	0.049*
C9	0.92019 (11)	0.8196 (2)	0.92674 (18)	0.0503 (5)
H9	0.8989	0.8143	0.9748	0.060*
C10	0.93107 (11)	0.9478 (2)	0.88954 (18)	0.0482 (5)
H10	0.9163	1.0302	0.9108	0.058*
C11	0.96472 (10)	0.95499 (17)	0.81881 (15)	0.0390 (4)
C12	0.98315 (8)	0.82583 (15)	0.78693 (13)	0.0290 (3)
C13	0.98266 (11)	1.0847 (2)	0.78170 (17)	0.0508 (5)
H13	0.9700	1.1703	0.8020	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.02088 (14)	0.02229 (15)	0.03263 (15)	0.000	0.00630 (10)	0.000
O1	0.0577 (8)	0.0624 (9)	0.0399 (7)	−0.0299 (7)	0.0174 (6)	−0.0169 (6)
O2	0.0269 (5)	0.0430 (6)	0.0418 (6)	−0.0118 (5)	0.0118 (5)	−0.0097 (5)
O3	0.0367 (7)	0.0751 (10)	0.0331 (6)	−0.0212 (6)	0.0091 (5)	0.0021 (6)
N1	0.0270 (6)	0.0291 (6)	0.0329 (6)	−0.0017 (5)	0.0132 (5)	−0.0011 (5)
C1	0.0248 (7)	0.0271 (8)	0.0398 (8)	−0.0029 (6)	0.0081 (6)	−0.0056 (6)
C2	0.0214 (7)	0.0311 (8)	0.0365 (8)	−0.0030 (5)	0.0101 (6)	−0.0066 (6)
C3	0.0246 (7)	0.0370 (8)	0.0344 (8)	−0.0036 (6)	0.0099 (6)	−0.0026 (6)
C4	0.0252 (7)	0.0353 (8)	0.0393 (8)	−0.0064 (6)	0.0124 (6)	−0.0027 (6)
C5	0.0450 (11)	0.0793 (15)	0.0469 (11)	−0.0162 (10)	0.0210 (9)	0.0023 (10)
C6	0.0535 (12)	0.0975 (19)	0.0473 (11)	−0.0056 (12)	0.0266 (10)	0.0018 (12)
C7	0.0639 (15)	0.103 (2)	0.0546 (13)	−0.0002 (14)	0.0251 (12)	−0.0175 (14)
C8	0.0395 (9)	0.0452 (10)	0.0427 (9)	−0.0084 (7)	0.0235 (8)	−0.0055 (7)
C9	0.0469 (10)	0.0625 (13)	0.0518 (11)	−0.0080 (9)	0.0320 (9)	−0.0180 (9)
C10	0.0451 (10)	0.0499 (11)	0.0482 (10)	0.0069 (8)	0.0211 (9)	−0.0151 (8)
C11	0.0418 (9)	0.0318 (9)	0.0348 (8)	0.0056 (7)	0.0113 (7)	−0.0054 (6)
C12	0.0271 (7)	0.0263 (7)	0.0275 (7)	0.0009 (5)	0.0082 (6)	−0.0016 (5)
C13	0.0718 (14)	0.0241 (8)	0.0441 (10)	0.0068 (8)	0.0175 (9)	−0.0022 (7)

Geometric parameters (Å, º) top

Zn1—O2	1.9647 (12)	C5—H5A	0.9700
Zn1—O2ⁱ	1.9647 (12)	C5—H5B	0.9700
Zn1—N1	2.0949 (14)	C6—C7	1.285 (4)
Zn1—N1ⁱ	2.0950 (14)	C6—H6	0.9300
O1—C1	1.232 (2)	C7—H7A	0.9300
O2—C1	1.270 (2)	C7—H7B	0.9300
O3—C3	1.365 (2)	C8—C9	1.392 (3)
O3—C5	1.418 (2)	C8—H8	0.9300
N1—C8	1.333 (2)	C9—C10	1.365 (3)
N1—C12	1.355 (2)	C9—H9	0.9300
C1—C2	1.510 (2)	C10—C11	1.408 (3)
C2—C4	1.392 (2)	C10—H10	0.9300
C2—C3	1.402 (2)	C11—C12	1.404 (2)
C3—C4ⁱⁱ	1.397 (2)	C11—C13	1.434 (3)
C4—C3ⁱⁱ	1.397 (2)	C12—C12ⁱ	1.444 (3)
C4—H4	0.9300	C13—C13ⁱ	1.342 (4)
C5—C6	1.484 (3)	C13—H13	0.9300

O2—Zn1—O2ⁱ	123.08 (8)	C6—C5—H5B	109.9
O2—Zn1—N1	113.91 (6)	H5A—C5—H5B	108.3
O2ⁱ—Zn1—N1	108.96 (6)	C7—C6—C5	126.0 (2)
O2—Zn1—N1ⁱ	108.96 (6)	C7—C6—H6	117.0
O2ⁱ—Zn1—N1ⁱ	113.91 (6)	C5—C6—H6	117.0
N1—Zn1—N1ⁱ	79.98 (8)	C6—C7—H7A	120.0
C1—O2—Zn1	105.59 (11)	C6—C7—H7B	120.0
C3—O3—C5	119.50 (14)	H7A—C7—H7B	120.0
C8—N1—C12	118.32 (14)	N1—C8—C9	122.23 (17)
C8—N1—Zn1	129.09 (11)	N1—C8—H8	118.9
C12—N1—Zn1	112.55 (10)	C9—C8—H8	118.9
O1—C1—O2	122.65 (14)	C10—C9—C8	119.77 (16)
O1—C1—C2	122.14 (15)	C10—C9—H9	120.1
O2—C1—C2	115.21 (14)	C8—C9—H9	120.1
C4—C2—C3	119.07 (14)	C9—C10—C11	119.75 (16)
C4—C2—C1	117.55 (14)	C9—C10—H10	120.1
C3—C2—C1	123.39 (15)	C11—C10—H10	120.1
O3—C3—C4ⁱⁱ	122.92 (15)	C12—C11—C10	116.75 (16)
O3—C3—C2	118.29 (14)	C12—C11—C13	119.27 (17)
C4ⁱⁱ—C3—C2	118.79 (15)	C10—C11—C13	123.96 (16)
C2—C4—C3ⁱⁱ	122.14 (15)	N1—C12—C11	123.14 (14)
C2—C4—H4	118.9	N1—C12—C12ⁱ	117.39 (8)
C3ⁱⁱ—C4—H4	118.9	C11—C12—C12ⁱ	119.47 (10)
O3—C5—C6	109.10 (18)	C13ⁱ—C13—C11	121.18 (11)
O3—C5—H5A	109.9	C13ⁱ—C13—H13	119.4
C6—C5—H5A	109.9	C11—C13—H13	119.4
O3—C5—H5B	109.9

O2ⁱ—Zn1—O2—C1	78.15 (10)	C3—C2—C4—C3ⁱⁱ	−0.5 (3)
N1—Zn1—O2—C1	−57.33 (12)	C1—C2—C4—C3ⁱⁱ	179.32 (15)
N1ⁱ—Zn1—O2—C1	−144.52 (10)	C3—O3—C5—C6	−160.82 (19)
O2—Zn1—N1—C8	72.39 (16)	O3—C5—C6—C7	9.4 (4)
O2ⁱ—Zn1—N1—C8	−69.20 (15)	C12—N1—C8—C9	2.2 (3)
N1ⁱ—Zn1—N1—C8	178.81 (18)	Zn1—N1—C8—C9	−175.24 (14)
O2—Zn1—N1—C12	−105.20 (11)	N1—C8—C9—C10	−1.0 (3)
O2ⁱ—Zn1—N1—C12	113.21 (11)	C8—C9—C10—C11	−1.3 (3)
N1ⁱ—Zn1—N1—C12	1.21 (7)	C9—C10—C11—C12	2.2 (3)
Zn1—O2—C1—O1	−3.4 (2)	C9—C10—C11—C13	−175.80 (19)
Zn1—O2—C1—C2	177.38 (10)	C8—N1—C12—C11	−1.2 (2)
O1—C1—C2—C4	157.66 (17)	Zn1—N1—C12—C11	176.68 (12)
O2—C1—C2—C4	−23.1 (2)	C8—N1—C12—C12ⁱ	178.70 (17)
O1—C1—C2—C3	−22.5 (2)	Zn1—N1—C12—C12ⁱ	−3.4 (2)
O2—C1—C2—C3	156.76 (15)	C10—C11—C12—N1	−1.0 (2)
C5—O3—C3—C4ⁱⁱ	−11.2 (3)	C13—C11—C12—N1	177.11 (15)
C5—O3—C3—C2	169.03 (18)	C10—C11—C12—C12ⁱ	179.11 (18)
C4—C2—C3—O3	−179.70 (15)	C13—C11—C12—C12ⁱ	−2.8 (3)
C1—C2—C3—O3	0.5 (2)	C12—C11—C13—C13ⁱ	−0.7 (3)
C4—C2—C3—C4ⁱⁱ	0.5 (3)	C10—C11—C13—C13ⁱ	177.2 (2)
C1—C2—C3—C4ⁱⁱ	−179.32 (14)

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

Experimental details

Crystal data
Chemical formula	[Zn(C₁₄H₁₂O₆)(C₁₂H₈N₂)]
M_r	521.81
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	21.428 (10), 9.458 (4), 12.897 (6)
β (°)	118.462 (5)
V (Å³)	2297.9 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.12
Crystal size (mm)	0.25 × 0.23 × 0.22

Data collection
Diffractometer	Bruker P4 diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.768, 0.792
No. of measured, independent and observed [I > 2σ(I)] reflections	8294, 2546, 2325
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.078, 1.04
No. of reflections	2546
No. of parameters	159
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.34

Computer programs: APEX2 (Bruker, 2007), SAINT-Plus (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors gratefully acknowledge support by Shandong Province Natural Science Foundation (grant No. ZR2009BM038), the Chinese Postdoctoral Science Foundation (grant No. 20090461212) and the Independent Innovation Foundation of Shandong University (grant No. 2009TS021).

References

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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhou, X. X., Liu, M. S., Lin, X. M., Fang, H. C., Chen, J. Q., Yang, D. Q. & Cai, Y. P. (2009). Inorg. Chim. Acta, 362, 1441–1447. CrossRef CAS Google Scholar

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