Terephthalic acid–4,4′-bipyridine (2/1)

Wang, S.; Yang, T.; Li, Z.; Yu, X.

doi:10.1107/S160053680903236X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2198

doi:10.1107/S160053680903236X

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RETRACTED ARTICLE

This article has been retracted. To view the retraction notice, click here.

Retracted: Terephthalic acid–4,4′-bipyridine (2/1)

Suwen Wang,^a Tianyu Yang,^b Zhongfang Li ^a ^* and Xianjin Yu ^a

^aCollege of Chemical Engineering, Shandong University of Technology, Zibo 255049, People's Republic of China, and ^bThe College of Life Sciences, Northwest University, Xi-An 710069, People's Republic of China
^*Correspondence e-mail: zhfli_sdut@yahoo.cn

(Received 4 August 2009; accepted 15 August 2009; online 22 August 2009)

In the title compound, 2C₈H₆O₄·C₁₀H₈N₂, the 4,4′-bipyridine molecule is located on an inversion centre. In the crystal structure, strong intermolecular O—H⋯N hydrogen bonds between the terephthalic acid and 4,4′-bipyridine molecules lead to the formation of chains with graph-set motif C₂²(8) along the diagonal of the bc plane.

Related literature

For the potential applications of metal-organic frameworks, see: Zhang et al. (2007 ); Zhang et al. (2009 ) For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

2C₈H₆O₄·C₁₀H₈N₂
M_r = 488.44
Monoclinic, P 2₁ /n
a = 7.788 (10) Å
b = 6.814 (8) Å
c = 20.77 (3) Å
β = 92.25 (2)°
V = 1102 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.27 × 0.19 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.971, T_max = 0.980
5164 measured reflections
1930 independent reflections
1192 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.178
S = 1.00
1930 reflections
169 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H2⋯N1	0.82 (2)	1.78 (2)	2.598 (4)	177.8 (14)

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001); 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/S160053680903236X/bx2232sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680903236X/bx2232Isup2.hkl

checkCIF report

Comment top

Design and construction of metal-organic frameworks (MOFs) have attracted considerable attention in recent years, not only for their intriguing structural motifs but also for their potential applications in the areas of catalysis, separation, gas adsorption, molecular recognition, nonlinear optics, and magnetochemistry (Zhang et al. (2007); Zhang et al. (2009)). The title compound was not the intended product of a reaction to make a MOFs. We report here the crystal and molecular structure of (I). The asymmetric unit of the title compound contains one terephthalic acid molecule and half 4,4'-bipyridine molecule, Fig. 1. The crystal structure is stabilized by strong intermolecular O—H··· N hydrogen bonds between terephthalic acid and 4,4'-bipyridine molecules, this interaction lead to the formation chains C₂²(8) (Bernstein, et al., 1995) along the diagonal of the bc-plane , Fig 2, Table 1.

Related literature top

For the potential applications of metal-organic frameworks, see: Zhang et al. (2007); Zhang et al. (2009) For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of terephthalic acid (1 mmoL), 4,4'-bipyridine (1 mmoL, 0.156 g), and iron trichloride (1 mmoL, 0.162 g) in 10 ml distilled water sealed in a 25 ml Teflon-lined stainless steel autoclave was kept at 433 K for three days. Colorless crystals suitable for the X-ray experiment were obtained. Anal. Calc. for C₂₆H₂₀N₂O₈: C 63.88, H 4.09, N 5.73%; Found: C 63.70, H 3.98, N 5.62%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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. A view of the structure of (I), showing the atomic numbering scheme and 30% probability displacement ellipsoids.
	Fig. 2. Packing diagram of (I). Dotted lines show hydrogen bonding.

terephthalic acid–4,4'-bipyridine (2/1) top

Crystal data top

2C₈H₆O₄·C₁₀H₈N₂	F(000) = 508
M_r = 488.44	D_x = 1.473 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1066 reflections
a = 7.788 (10) Å	θ = 2.8–23.0°
b = 6.814 (8) Å	µ = 0.11 mm⁻¹
c = 20.77 (3) Å	T = 296 K
β = 92.25 (2)°	Block, colorless
V = 1102 (2) Å³	0.27 × 0.19 × 0.18 mm
Z = 2

Data collection top

Bruker APEXII CCD area-detector diffractometer	1930 independent reflections
Radiation source: fine-focus sealed tube	1192 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.971, T_max = 0.980	k = −8→6
5164 measured reflections	l = −24→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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.178	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.098P)² + 0.1551P] where P = (F_o² + 2F_c²)/3
1930 reflections	(Δ/σ)_max = 0.001
169 parameters	Δρ_max = 0.20 e Å⁻³
2 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

2C₈H₆O₄·C₁₀H₈N₂	V = 1102 (2) Å³
M_r = 488.44	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.788 (10) Å	µ = 0.11 mm⁻¹
b = 6.814 (8) Å	T = 296 K
c = 20.77 (3) Å	0.27 × 0.19 × 0.18 mm
β = 92.25 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	1930 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1192 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.980	R_int = 0.028
5164 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	2 restraints
wR(F²) = 0.178	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.20 e Å⁻³
1930 reflections	Δρ_min = −0.23 e Å⁻³
169 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
C1	1.1228 (3)	1.5441 (4)	0.21096 (13)	0.0521 (7)
C2	1.0571 (3)	1.3616 (4)	0.18496 (13)	0.0568 (7)
C3	1.0878 (4)	1.3136 (4)	0.12209 (14)	0.0652 (8)
H3	1.1497	1.3981	0.0966	0.078*
C4	1.0260 (3)	1.1400 (4)	0.09756 (13)	0.0615 (7)
H4	1.0458	1.1057	0.0552	0.074*
C5	0.9345 (3)	1.0161 (4)	0.13570 (12)	0.0531 (7)
C6	0.8676 (3)	0.8295 (4)	0.10696 (13)	0.0594 (7)
C7	0.9048 (3)	1.0691 (4)	0.19886 (13)	0.0616 (8)
H7	0.8420	0.9859	0.2245	0.074*
C8	0.9666 (3)	1.2420 (4)	0.22379 (13)	0.0615 (7)
H8	0.9475	1.2771	0.2662	0.074*
C9	0.6969 (4)	0.3813 (4)	0.02420 (16)	0.0782 (9)
H9	0.7712	0.4676	0.0046	0.094*
C10	0.6398 (4)	0.2208 (4)	−0.00991 (15)	0.0758 (9)
H10	0.6744	0.2015	−0.0518	0.091*
C11	0.5323 (3)	0.0887 (3)	0.01718 (13)	0.0519 (7)
C12	0.4889 (3)	0.1285 (4)	0.07984 (14)	0.0655 (8)
H12	0.4178	0.0426	0.1012	0.079*
C13	0.5501 (4)	0.2936 (4)	0.11059 (14)	0.0688 (8)
H13	0.5178	0.3167	0.1525	0.083*
N1	0.6518 (3)	0.4205 (3)	0.08396 (11)	0.0632 (7)
O1	1.2080 (3)	1.6465 (4)	0.17755 (14)	0.0971 (8)
O2	1.0894 (3)	1.5957 (3)	0.26370 (13)	0.1001 (8)
O3	0.9023 (3)	0.7783 (3)	0.05288 (10)	0.0876 (7)
O4	0.7709 (3)	0.7296 (3)	0.14372 (10)	0.0740 (6)
H1	1.2411	1.7424	0.1966	0.146*
H2	0.732 (3)	0.634 (3)	0.1242 (13)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0583 (16)	0.0482 (15)	0.0498 (16)	−0.0067 (12)	0.0016 (13)	−0.0059 (13)
C2	0.0580 (16)	0.0590 (16)	0.0531 (16)	0.0056 (12)	−0.0013 (13)	−0.0056 (13)
C3	0.0746 (18)	0.0663 (17)	0.0554 (17)	−0.0053 (14)	0.0115 (14)	−0.0004 (14)
C4	0.0753 (18)	0.0649 (17)	0.0452 (16)	−0.0029 (14)	0.0132 (13)	−0.0048 (13)
C5	0.0594 (15)	0.0560 (15)	0.0439 (15)	0.0040 (12)	0.0033 (12)	−0.0003 (12)
C6	0.0703 (17)	0.0568 (15)	0.0515 (17)	−0.0001 (13)	0.0079 (14)	0.0009 (13)
C7	0.0730 (18)	0.0671 (17)	0.0454 (16)	−0.0052 (13)	0.0106 (13)	0.0006 (13)
C8	0.0702 (17)	0.0695 (18)	0.0451 (15)	0.0023 (14)	0.0052 (13)	−0.0081 (13)
C9	0.103 (2)	0.0695 (19)	0.064 (2)	−0.0242 (17)	0.0162 (18)	0.0023 (16)
C10	0.106 (2)	0.0689 (18)	0.0530 (18)	−0.0249 (17)	0.0161 (17)	−0.0045 (15)
C11	0.0536 (15)	0.0519 (14)	0.0501 (15)	0.0024 (11)	−0.0001 (12)	0.0001 (12)
C12	0.0717 (18)	0.0655 (17)	0.0603 (18)	−0.0128 (14)	0.0139 (15)	−0.0041 (14)
C13	0.0780 (19)	0.0737 (19)	0.0556 (18)	−0.0069 (15)	0.0138 (15)	−0.0087 (15)
N1	0.0732 (15)	0.0586 (14)	0.0579 (15)	−0.0049 (11)	0.0043 (12)	0.0007 (11)
O1	0.1010 (18)	0.0836 (17)	0.105 (2)	−0.0092 (14)	−0.0137 (17)	−0.0178 (15)
O2	0.1216 (19)	0.0888 (16)	0.0897 (19)	−0.0073 (13)	0.0038 (15)	−0.0325 (14)
O3	0.1339 (18)	0.0751 (14)	0.0559 (13)	−0.0234 (12)	0.0306 (12)	−0.0190 (11)
O4	0.0982 (15)	0.0655 (13)	0.0594 (13)	−0.0208 (11)	0.0183 (11)	−0.0096 (10)

Geometric parameters (Å, º) top

C1—O2	1.189 (3)	C8—H8	0.9300
C1—O1	1.202 (4)	C9—N1	1.330 (4)
C1—C2	1.441 (4)	C9—C10	1.368 (4)
C2—C8	1.362 (4)	C9—H9	0.9300
C2—C3	1.376 (4)	C10—C11	1.366 (4)
C3—C4	1.368 (4)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.384 (4)
C4—C5	1.375 (3)	C11—C11ⁱ	1.482 (5)
C4—H4	0.9300	C12—C13	1.370 (4)
C5—C7	1.389 (4)	C12—H12	0.9300
C5—C6	1.491 (4)	C13—N1	1.309 (3)
C6—O3	1.217 (3)	C13—H13	0.9300
C6—O4	1.288 (3)	O1—H1	0.8000
C7—C8	1.367 (4)	O4—H2	0.82 (2)
C7—H7	0.9300

O2—C1—O1	120.4 (3)	C2—C8—C7	118.3 (3)
O2—C1—C2	120.9 (3)	C2—C8—H8	120.9
O1—C1—C2	118.7 (3)	C7—C8—H8	120.8
O2—C1—H1	94.0	N1—C9—C10	123.4 (3)
C2—C1—H1	145.0	N1—C9—H9	118.3
C8—C2—C3	122.2 (3)	C10—C9—H9	118.3
C8—C2—C1	118.6 (3)	C11—C10—C9	120.4 (3)
C3—C2—C1	119.2 (3)	C11—C10—H10	119.8
C4—C3—C2	119.2 (3)	C9—C10—H10	119.8
C4—C3—H3	120.4	C10—C11—C12	115.8 (2)
C2—C3—H3	120.4	C10—C11—C11ⁱ	122.8 (3)
C3—C4—C5	119.9 (3)	C12—C11—C11ⁱ	121.4 (3)
C3—C4—H4	120.0	C13—C12—C11	120.4 (3)
C5—C4—H4	120.0	C13—C12—H12	119.8
C4—C5—C7	119.6 (3)	C11—C12—H12	119.8
C4—C5—C6	118.3 (2)	N1—C13—C12	123.4 (3)
C7—C5—C6	122.1 (2)	N1—C13—H13	118.3
O3—C6—O4	123.5 (3)	C12—C13—H13	118.3
O3—C6—C5	121.8 (2)	C13—N1—C9	116.6 (2)
O4—C6—C5	114.6 (2)	C13—N1—H2	123.3 (10)
C8—C7—C5	120.8 (2)	C9—N1—H2	120.1 (10)
C8—C7—H7	119.6	C1—O1—H1	111.00
C5—C7—H7	119.6	C6—O4—H2	110 (2)

C13—N1—C9—C10	1.7 (5)	C1—C2—C3—C4	179.7 (2)
N1—C9—C10—C11	−0.9 (5)	C2—C3—C4—C5	−0.2 (4)
C9—C10—C11—C12	−0.6 (4)	C3—C4—C5—C7	0.4 (4)
C9—C10—C11—C11ⁱ	−179.2 (3)	C3—C4—C5—C6	179.4 (2)
C10—C11—C12—C13	1.3 (4)	C4—C5—C6—O3	5.4 (4)
C11ⁱ—C11—C12—C13	179.9 (3)	C7—C5—C6—O3	−175.6 (3)
C9—N1—C13—C12	−1.0 (4)	C4—C5—C6—O4	−174.3 (2)
C11—C12—C13—N1	−0.5 (4)	C7—C5—C6—O4	4.7 (4)
O2—C1—C2—C8	−5.1 (4)	C4—C5—C7—C8	−0.5 (4)
O1—C1—C2—C8	177.3 (3)	C6—C5—C7—C8	−179.5 (2)
O2—C1—C2—C3	175.2 (3)	C3—C2—C8—C7	−0.2 (4)
O1—C1—C2—C3	−2.6 (4)	C1—C2—C8—C7	−179.8 (2)
C8—C2—C3—C4	0.1 (4)	C5—C7—C8—C2	0.4 (4)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H2···N1	0.82 (2)	1.78 (2)	2.598 (4)	178 (1)

Experimental details

Crystal data
Chemical formula	2C₈H₆O₄·C₁₀H₈N₂
M_r	488.44
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	7.788 (10), 6.814 (8), 20.77 (3)
β (°)	92.25 (2)
V (Å³)	1102 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.27 × 0.19 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.971, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	5164, 1930, 1192
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.178, 1.00
No. of reflections	1930
No. of parameters	169
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.23

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H2···N1	0.82 (2)	1.78 (2)	2.598 (4)	177.8 (14)

Acknowledgements

The authors thank the NSFC (grant No. 20776081) and the Natural Science Foundation of Shandong Province (grant No. Y2006B37).

References

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