4,4′-Azinodibenzoic acid

Yu, Q.-D.; Liu, Y.-Y.

doi:10.1107/S1600536809033224

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2326

doi:10.1107/S1600536809033224

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4,4′-Azinodibenzoic acid

Qun-Di Yu ^a and Yun-Yu Liu ^b ^*

^aFood Science and Pharmacy College, Zhejiang Ocean University, Zhoushan 316000, People's Republic of China, and ^bDepartment of Chemistry, Northeast Normal University, Changchun 130024, People's Republic of China
^*Correspondence e-mail: yunyuliu888@yahoo.com.cn

(Received 13 August 2009; accepted 20 August 2009; online 5 September 2009)

The title compound, C₁₄H₁₀N₂O₄, shows crystallographic inversion symmetry and has one half-molecule in the asymmetric unit. In the crystal, molecules are linked into chains running along the cell diagonal by O—H⋯O hydrogen-bonding interactions.

Related literature

For the use of azodibenzoate-based systems as bridging aromatic carboxylate ligands in coordination networks, see: Chen et al. (2008 ).

Experimental

Crystal data

C₁₄H₁₀N₂O₄
M_r = 270.16
Triclinic, $[P \overline 1]$
a = 3.772 (2) Å
b = 6.322 (5) Å
c = 12.692 (3) Å
α = 79.323 (5)°
β = 88.199 (4)°
γ = 88.435 (5)°
V = 297.2 (3) Å³
Z = 1
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.16 × 0.14 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick 1996 ) T_min = 0.962, T_max = 0.971
2173 measured reflections
1351 independent reflections
786 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.100
S = 0.86
1351 reflections
91 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2ⁱ	0.82	1.81	2.6181 (17)	170
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); 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/S1600536809033224/bt5033sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809033224/bt5033Isup2.hkl

checkCIF report

Comment top

Azodibenzoate-based systems represent one type of bridging aromatic carboxylate ligand employed in the generation of coordination networks (Chen et al., 2008). There is half a molecule in the asymmetric unit of the title compound (Fig. 1). In the crystal, molecules are linked into chains by O—H···O hydrogen-bonding interactions (Table 2).

Related literature top

For the use of azodibenzoate-based systems as bridging aromatic carboxylate ligands in coordination networks, see: Chen et al. (2008).

Experimental top

A mixture of ZnCl₂^.2H₂O (0.5 mmol), 4,4'-azodibenzoatic acid (0.5 mmol), and H₂O (500 mmol) was heated at 140 ^oC for 3 days. After the mixture was slowly cooled to room temperature, pale yellow crystals of the title compound were yielded (22% yield).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Symmetry code: (i) -x, -y, -z.

4,4'-Azinodibenzoic acid top

Crystal data top

C₁₄H₁₀N₂O₄	Z = 1
M_r = 270.16	F(000) = 140
Triclinic, P1	D_x = 1.509 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 3.772 (2) Å	Cell parameters from 1351 reflections
b = 6.322 (5) Å	θ = 3.0–29.0°
c = 12.692 (3) Å	µ = 0.11 mm⁻¹
α = 79.323 (5)°	T = 293 K
β = 88.199 (4)°	Block, pale yellow
γ = 88.435 (5)°	0.16 × 0.14 × 0.12 mm
V = 297.2 (3) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1351 independent reflections
Radiation source: fine-focus sealed tube	786 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ϕ and ω scans	θ_max = 29.0°, θ_min = 3.3°
Absorption correction: multi-scan (SADABS; Sheldrick 1996)	h = −5→4
T_min = 0.962, T_max = 0.971	k = −8→5
2173 measured reflections	l = −17→17

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 0.86	w = 1/[σ²(F_o²) + (0.0555P)²] where P = (F_o² + 2F_c²)/3
1351 reflections	(Δ/σ)_max < 0.001
91 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₄H₁₀N₂O₄	γ = 88.435 (5)°
M_r = 270.16	V = 297.2 (3) Å³
Triclinic, P1	Z = 1
a = 3.772 (2) Å	Mo Kα radiation
b = 6.322 (5) Å	µ = 0.11 mm⁻¹
c = 12.692 (3) Å	T = 293 K
α = 79.323 (5)°	0.16 × 0.14 × 0.12 mm
β = 88.199 (4)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1351 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick 1996)	786 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.971	R_int = 0.017
2173 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 0.86	Δρ_max = 0.19 e Å⁻³
1351 reflections	Δρ_min = −0.19 e Å⁻³
91 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	0.0410 (4)	−0.0391 (3)	0.23081 (12)	0.0356 (4)
H1	−0.0514	−0.1767	0.2450	0.043*
C2	0.1284 (4)	0.0608 (3)	0.31492 (12)	0.0343 (4)
H2	0.0924	−0.0090	0.3855	0.041*
C3	0.2692 (4)	0.2646 (2)	0.29319 (11)	0.0292 (4)
C4	0.3691 (4)	0.3697 (2)	0.38301 (12)	0.0315 (4)
C5	0.3203 (4)	0.3700 (2)	0.18790 (12)	0.0337 (4)
H5	0.4147	0.5070	0.1738	0.040*
C6	0.2312 (4)	0.2720 (3)	0.10404 (12)	0.0355 (4)
H6	0.2640	0.3426	0.0334	0.043*
C7	0.0913 (4)	0.0659 (2)	0.12647 (12)	0.0315 (4)
N1	−0.0103 (4)	−0.0518 (2)	0.04644 (9)	0.0372 (4)
O1	0.2870 (4)	0.2717 (2)	0.47782 (9)	0.0545 (4)
H1A	0.3524	0.3417	0.5217	0.082*
O2	0.5255 (3)	0.54435 (18)	0.36449 (9)	0.0453 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0452 (10)	0.0306 (9)	0.0329 (9)	−0.0099 (7)	−0.0026 (7)	−0.0095 (7)
C2	0.0438 (10)	0.0360 (9)	0.0243 (8)	−0.0081 (8)	−0.0014 (7)	−0.0072 (7)
C3	0.0321 (9)	0.0322 (8)	0.0261 (8)	−0.0037 (7)	−0.0030 (6)	−0.0115 (7)
C4	0.0377 (9)	0.0334 (9)	0.0253 (8)	−0.0060 (7)	−0.0040 (6)	−0.0092 (7)
C5	0.0436 (10)	0.0295 (8)	0.0299 (9)	−0.0082 (7)	−0.0009 (7)	−0.0092 (7)
C6	0.0465 (10)	0.0376 (9)	0.0240 (8)	−0.0067 (7)	−0.0030 (7)	−0.0084 (7)
C7	0.0333 (9)	0.0349 (9)	0.0299 (9)	−0.0023 (7)	−0.0048 (7)	−0.0144 (7)
N1	0.0471 (8)	0.0382 (8)	0.0300 (7)	−0.0081 (7)	−0.0058 (7)	−0.0143 (6)
O1	0.0875 (10)	0.0544 (8)	0.0254 (6)	−0.0314 (7)	−0.0023 (6)	−0.0128 (6)
O2	0.0674 (8)	0.0397 (7)	0.0321 (7)	−0.0215 (6)	−0.0027 (6)	−0.0119 (5)

Geometric parameters (Å, º) top

C1—C7	1.377 (2)	C4—O1	1.2800 (18)
C1—C2	1.389 (2)	C5—C6	1.381 (2)
C1—H1	0.9300	C5—H5	0.9300
C2—C3	1.384 (2)	C6—C7	1.396 (2)
C2—H2	0.9300	C6—H6	0.9300
C3—C5	1.388 (2)	C7—N1	1.4327 (19)
C3—C4	1.485 (2)	N1—N1ⁱ	1.239 (2)
C4—O2	1.246 (2)	O1—H1A	0.8200

C7—C1—C2	119.91 (16)	C6—C5—C3	120.22 (15)
C7—C1—H1	120.0	C6—C5—H5	119.9
C2—C1—H1	120.0	C3—C5—H5	119.9
C3—C2—C1	119.70 (15)	C5—C6—C7	119.22 (15)
C3—C2—H2	120.2	C5—C6—H6	120.4
C1—C2—H2	120.2	C7—C6—H6	120.4
C2—C3—C5	120.28 (14)	C1—C7—C6	120.67 (14)
C2—C3—C4	119.73 (14)	C1—C7—N1	115.05 (15)
C5—C3—C4	119.99 (15)	C6—C7—N1	124.28 (14)
O2—C4—O1	123.10 (14)	N1ⁱ—N1—C7	114.04 (17)
O2—C4—C3	120.27 (14)	C4—O1—H1A	109.5
O1—C4—C3	116.63 (15)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2ⁱⁱ	0.82	1.81	2.6181 (17)	170

Symmetry code: (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀N₂O₄
M_r	270.16
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	3.772 (2), 6.322 (5), 12.692 (3)
α, β, γ (°)	79.323 (5), 88.199 (4), 88.435 (5)
V (Å³)	297.2 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.16 × 0.14 × 0.12

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick 1996)
T_min, T_max	0.962, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	2173, 1351, 786
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.681

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.100, 0.86
No. of reflections	1351
No. of parameters	91
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.19

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), 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
O1—H1A···O2ⁱ	0.82	1.81	2.6181 (17)	170.0

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

We thank Zhejiang Ocean University and the Science Foundation for Young Teachers of Northeast Normal University (No. 20080305) for support.

References

Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, Z.-F., Zhang, Z.-L., Tan, Y.-H., Tang, Y.-Z., Fun, H.-K., Zhou, Z.-Y., Abrahams, B. F. & Liang, H. (2008). CrystEngComm, 10, 217–231. Web of Science CSD CrossRef 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