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

Xiao, W.; Xue, R.; Yin, Y.

doi:10.1107/S1600536811016448

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1333

doi:10.1107/S1600536811016448

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

Wenzhi Xiao,^a Ruiting Xue ^b and Yansheng Yin ^b ^*

^aDepartment of Physics and Mathematics, Hunan Institute of Engineering, Xiangtan 411104, People's Republic of China, and ^bInstitute of Material Science and Engineering, Ocean University of China, Qingdao, Shandong 266100, People's Republic of China
^*Correspondence e-mail: xuert@163.com

(Received 29 April 2011; accepted 30 April 2011; online 7 May 2011)

The asymmetric unit of the title compound, C₁₀H₈N₂·C₈H₇NO₄, contains two half-molecules, which constitute a 1:1 co-crystal. The 2-aminoterephthalic acid molecule is situated on an inversion center being disordered between two orientations in a 1:1 ratio. In the 4,4′-bipyridine molecule, which is situated on a twofold rotational axis, the two pyridine rings form a dihedral angle of 37.5 (1)°. In the crystal, molecules are held together via intermolecular N—H⋯O and O—H⋯N hydrogen bonds. The crystal packing exhibits π–π interactions 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_r = 337.33
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.067
wR(F²) = 0.199
S = 1.00
1370 reflections
118 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.29 e Å⁻³

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) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (iii) $[-x+1, y, -z+{\script{3\over 2}}]$ .

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.

Supporting information

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

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

Supporting information file. DOI: 10.1107/S1600536811016448/cv5085Isup3.cml

checkCIF report

Comment top

Bipyridine is a well known molecule often used as a linker in polymeric coordination compounds. 2-Aminoterephthalic acid is also sometimes used as a linker in polymeric compounds (Ma et al., 2005; Bauer et al., 2008). The title compound (I) is a 1:1 cocrystal of the aforementioned linkers. Herewith we present its crystal structure.

In (I) (Fig. 1), the 2-aminoterephthalic acid molecule is situated on an inversion center, therefore, it is disordered (namely, the amino group is disordered between two positions). The carboxyl groups are twisted from the benzene ring plane at 11.4 (1)°. The 4,4'-bipyridine molecule is situated on a twofold rotational axis, and two pyridine rings form a dihedral angle of 37.5 (1)°.

In the crystal structure, the molecules are held together via intermolecular N—H···O and O—H···N hydrogen bonds. The crystal packing exhibits π—π interactions between the aromatic rings with the centroid-to-centroid distance of 3.722 (3) Å.

Related literature top

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

Experimental top

2-Diaminoterephthalic acid(10 mmol) and 4,4'-bipyridine(10 mmol) were dissolved to methanol (10 ml) and then hydrochloric acid(5 ml) was added. A few minutes later, an methanol solution (10 ml) of tin tetrachloride (5 mmol) was added with stirring. The reaction mixture was stirred for 4 h. The solution was held at room temperature for about two weeks, whereupon yellow crystals of the title compound, which were beyond expectations, were obtained.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (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. The structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. (symmetry code A: x + 3/2, -y + 3/2, -z and B: -x + 1, y, -z + 3/2). For the disordered molecule of 2-aminoterephthalic acid, only one orientation is shown.

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

Crystal data top

C₁₀H₈N₂·C₈H₇NO₄	F(000) = 704
M_r = 337.33	D_x = 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

Data collection top

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

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.199	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.1295P)²] where P = (F_o² + 2F_c²)/3
1370 reflections	(Δ/σ)_max < 0.001
118 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₀H₈N₂·C₈H₇NO₄	V = 1564.4 (3) Å³
M_r = 337.33	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 16.9501 (18) Å	µ = 0.10 mm⁻¹
b = 11.1959 (13) Å	T = 293 K
c = 9.251 (1) Å	0.33 × 0.19 × 0.11 mm
β = 116.986 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1370 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	894 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.989	R_int = 0.075
3865 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.199	H-atom parameters constrained
S = 1.00	Δρ_max = 0.32 e Å⁻³
1370 reflections	Δρ_min = −0.29 e Å⁻³
118 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	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

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

Hydrogen-bond geometry (Å, º) top

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

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

Experimental details

Crystal data
Chemical formula	C₁₀H₈N₂·C₈H₇NO₄
M_r	337.33
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	16.9501 (18), 11.1959 (13), 9.251 (1)
β (°)	116.986 (2)
V (Å³)	1564.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.33 × 0.19 × 0.11

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.967, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	3865, 1370, 894
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.199, 1.00
No. of reflections	1370
No. of parameters	118
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.29

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), 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
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) −x+3/2, y+1/2, −z+1/2; (ii) −x+3/2, −y+3/2, −z; (iii) −x+1, y, −z+3/2.

Acknowledgements

The authors acknowledge the Scientific Research Fund of Hunan Provincial Education Department (grant No. 10 C0559) and the National Science Foundation of China (grant No. 50672090).

References

Bauer, S., Serre, C., Devic, T., Horcajada, P., Marrot, J., Ferey, G. & Stock, N. (2008). Inorg. Chem. 47, 7568–7576. Web of Science CSD CrossRef PubMed CAS Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ma, A.-Q., Cai, G.-Q. & Zhu, L.-G. (2005). Z. Kristallogr. New Cryst. Struct. 220, 139–140. 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