Terephthalic acid-4,4'-bipyridine (2/1).

In the title compound, 2C(8)H(6)O(4)·C(10)H(8)N(2), the 4,4'-bipyridine mol-ecule is located on an inversion centre. In the crystal structure, strong inter-molecular O-H⋯N hydrogen bonds between the terephthalic acid and 4,4'-bipyridine mol-ecules lead to the formation of chains with graph-set motif C(2) (2)(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 = 488.44

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.178

S = 1.00

1930 reflections

169 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.23 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680903236X/bx2232sup1.cif

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

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

2C8H6O4·C10H8N2	F(000) = 508
Mr = 488.44	Dx = 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

Bruker APEXII CCD area-detector diffractometer	1930 independent reflections
Radiation source: fine-focus sealed tube	1192 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
Tmin = 0.971, Tmax = 0.980	k = −8→6
5164 measured reflections	l = −24→16

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(Fo2) + (0.098P)2 + 0.1551P] where P = (Fo2 + 2Fc2)/3
1930 reflections	(Δ/σ)max = 0.001
169 parameters	Δρmax = 0.20 e Å−3
2 restraints	Δρmin = −0.23 e Å−3

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	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*

	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)

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)

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)

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)