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

The asymmetric unit of the title compound, C(10)H(8)N(2)·C(8)H(7)NO(4), contains two half-mol-ecules, which constitute a 1:1 co-crystal. The 2-amino-terephthalic acid mol-ecule is situated on an inversion center being disordered between two orientations in a 1:1 ratio. In the 4,4'-bipyridine mol-ecule, which is situated on a twofold rotational axis, the two pyridine rings form a dihedral angle of 37.5 (1)°. In the crystal, mol-ecules are held together via inter-molecular N-H⋯O and O-H⋯N hydrogen bonds. The crystal packing exhibits π-π inter-actions between the aromatic rings with a centroid-centroid distance of 3.722 (3) Å.

Related literature

For the crystal structures of polymeric coordination polymers with 2-amino­terephthalic acid linkers, see: Ma et al. (2005) ▶; Bauer et al. (2008 ▶).

Experimental

Crystal data

C10H8N2·C8H7NO4

M = 337.33

Monoclinic,

a = 16.9501 (18) Å

b = 11.1959 (13) Å

c = 9.251 (1) Å

β = 116.986 (2)°

V = 1564.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.33 × 0.19 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.967, T max = 0.989

3865 measured reflections

1370 independent reflections

894 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.199

S = 1.00

1370 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811016448/cv5085sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016448/cv5085Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811016448/cv5085Isup3.cml

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

C10H8N2·C8H7NO4	F(000) = 704
Mr = 337.33	Dx = 1.432 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.9501 (18) Å	Cell parameters from 1178 reflections
b = 11.1959 (13) Å	θ = 2.3–26.0°
c = 9.251 (1) Å	µ = 0.10 mm−1
β = 116.986 (2)°	T = 293 K
V = 1564.4 (3) Å3	Block, yellow
Z = 4	0.33 × 0.19 × 0.11 mm

Bruker SMART CCD area-detector diffractometer	1370 independent reflections
Radiation source: fine-focus sealed tube	894 reflections with I > 2σ(I)
graphite	Rint = 0.075
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→12
Tmin = 0.967, Tmax = 0.989	k = −11→13
3865 measured reflections	l = −10→10

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.199	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.1295P)2] where P = (Fo2 + 2Fc2)/3
1370 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.29 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	Occ. (<1)
N1	0.8270 (3)	0.9576 (4)	−0.0096 (6)	0.0607 (13)	0.50
H1A	0.8317	1.0134	0.0577	0.073*	0.50
H1B	0.8478	0.9678	−0.0779	0.073*	0.50
N2	0.39951 (15)	0.8071 (2)	1.0092 (3)	0.0600 (7)
O1	0.67530 (15)	0.82272 (19)	0.2964 (3)	0.0742 (8)
H1	0.6550	0.8097	0.3602	0.111*
O2	0.65519 (15)	0.62839 (19)	0.2565 (3)	0.0711 (7)
C1	0.68006 (18)	0.7229 (3)	0.2283 (3)	0.0520 (8)
C2	0.71594 (15)	0.7367 (2)	0.1106 (3)	0.0436 (7)
C3	0.75521 (17)	0.8419 (2)	0.1014 (3)	0.0459 (7)
H3	0.7595	0.9041	0.1713	0.055*
C4	0.78845 (17)	0.8581 (2)	−0.0081 (3)	0.0462 (7)
H4	0.8134	0.9307	−0.0140	0.055*	0.50
C5	0.39774 (19)	0.9000 (3)	0.9217 (3)	0.0594 (8)
H5	0.3689	0.9685	0.9295	0.071*
C6	0.43583 (18)	0.9020 (2)	0.8196 (3)	0.0529 (8)
H6	0.4328	0.9707	0.7606	0.063*
C7	0.47874 (16)	0.8020 (2)	0.8042 (3)	0.0451 (7)
C8	0.47940 (19)	0.7037 (3)	0.8939 (3)	0.0564 (8)
H8	0.5062	0.6331	0.8861	0.068*
C9	0.4404 (2)	0.7104 (3)	0.9947 (4)	0.0646 (9)
H9	0.4427	0.6436	1.0563	0.077*

	U11	U22	U33	U12	U13	U23
N1	0.094 (4)	0.048 (2)	0.071 (3)	−0.013 (2)	0.064 (3)	−0.013 (2)
N2	0.0592 (15)	0.0888 (17)	0.0500 (14)	−0.0024 (13)	0.0404 (13)	0.0035 (12)
O1	0.1089 (18)	0.0821 (14)	0.0749 (15)	0.0006 (12)	0.0797 (15)	−0.0074 (11)
O2	0.0983 (17)	0.0765 (14)	0.0719 (15)	0.0073 (12)	0.0679 (14)	0.0144 (11)
C1	0.0551 (16)	0.0688 (19)	0.0402 (15)	0.0119 (14)	0.0287 (13)	0.0078 (13)
C2	0.0456 (14)	0.0573 (15)	0.0366 (14)	0.0069 (12)	0.0264 (12)	0.0046 (11)
C3	0.0504 (15)	0.0575 (15)	0.0381 (14)	0.0071 (12)	0.0273 (13)	−0.0029 (11)
C4	0.0520 (16)	0.0550 (15)	0.0440 (15)	0.0023 (12)	0.0324 (13)	0.0046 (11)
C5	0.0643 (18)	0.0808 (19)	0.0509 (18)	0.0050 (15)	0.0416 (16)	−0.0027 (14)
C6	0.0640 (17)	0.0658 (17)	0.0448 (15)	0.0036 (14)	0.0385 (14)	0.0031 (12)
C7	0.0429 (14)	0.0644 (16)	0.0342 (13)	−0.0031 (12)	0.0229 (12)	−0.0010 (11)
C8	0.0624 (17)	0.0661 (17)	0.0552 (17)	0.0057 (14)	0.0394 (15)	0.0089 (13)
C9	0.073 (2)	0.0802 (19)	0.0576 (18)	−0.0005 (16)	0.0443 (17)	0.0180 (15)

N1—C4	1.295 (5)	C3—H3	0.9300
N1—H1A	0.8600	C4—C2i	1.403 (4)
N1—H1B	0.8600	C4—H4	0.9300
N2—C5	1.310 (3)	C5—C6	1.365 (3)
N2—C9	1.325 (4)	C5—H5	0.9300
O1—C1	1.304 (3)	C6—C7	1.378 (3)
O1—H1	0.8200	C6—H6	0.9300
O2—C1	1.210 (3)	C7—C8	1.376 (3)
C1—C2	1.476 (4)	C7—C7ii	1.477 (5)
C2—C3	1.374 (4)	C8—C9	1.368 (4)
C2—C4i	1.403 (4)	C8—H8	0.9300
C3—C4	1.376 (4)	C9—H9	0.9300
C4—N1—H1A	120.0	C3—C4—H4	120.5
C4—N1—H1B	120.0	C2i—C4—H4	120.5
H1A—N1—H1B	120.0	N2—C5—C6	123.8 (3)
C5—N2—C9	116.9 (2)	N2—C5—H5	118.1
C1—O1—H1	109.5	C6—C5—H5	118.1
O2—C1—O1	122.8 (3)	C5—C6—C7	119.7 (3)
O2—C1—C2	123.5 (3)	C5—C6—H6	120.1
O1—C1—C2	113.7 (3)	C7—C6—H6	120.1
C3—C2—C4i	119.0 (2)	C8—C7—C6	116.6 (2)
C3—C2—C1	120.6 (2)	C8—C7—C7ii	122.47 (18)
C4i—C2—C1	120.4 (2)	C6—C7—C7ii	120.88 (17)
C2—C3—C4	122.0 (2)	C9—C8—C7	119.5 (3)
C2—C3—H3	119.0	C9—C8—H8	120.2
C4—C3—H3	119.0	C7—C8—H8	120.2
N1—C4—C3	119.8 (3)	N2—C9—C8	123.4 (3)
N1—C4—C2i	121.1 (3)	N2—C9—H9	118.3
C3—C4—C2i	119.0 (2)	C8—C9—H9	118.3
N1—C4—H4	3.0

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2iii	0.86	2.08	2.931 (5)	172
N1—H1B···O2i	0.86	1.95	2.619 (5)	133
O1—H1···N2ii	0.82	1.82	2.635 (3)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.86	2.08	2.931 (5)	172
N1—H1B⋯O2ii	0.86	1.95	2.619 (5)	133
O1—H1⋯N2iii	0.82	1.82	2.635 (3)	170

Symmetry codes: (i) ; (ii) ; (iii) .