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Acta Cryst. (2009). E65, o2326    [ doi:10.1107/S1600536809033224 ]

4,4'-Azinodibenzoic acid

Q.-D. Yu and Y.-Y. Liu

Abstract top

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.

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).

Refinement top

All H atoms on C atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding, with Uiso(H)=1.2Ueq(carrier).

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
[Figure 1] 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
C14H10N2O4Z = 1
Mr = 270.16F(000) = 140
Triclinic, P1Dx = 1.509 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 3.772 (2) ÅCell parameters from 1351 reflections
b = 6.322 (5) Åθ = 3.0–29.0°
c = 12.692 (3) ŵ = 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 tube786 reflections with I > 2σ(I)
graphiteRint = 0.017
φ and ω scansθmax = 29.0°, θmin = 3.3°
Absorption correction: multi-scan
(SADABS; Sheldrick 1996)		h = −5→4
Tmin = 0.962, Tmax = 0.971k = −8→5
2173 measured reflectionsl = −17→17
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 0.86 w = 1/[σ2(Fo2) + (0.0555P)2]
where P = (Fo2 + 2Fc2)/3
1351 reflections(Δ/σ)max < 0.001
91 parametersΔρmax = 0.19 e Å−3
0 restraintsΔρmin = −0.19 e Å−3
Crystal data top
C14H10N2O4γ = 88.435 (5)°
Mr = 270.16V = 297.2 (3) Å3
Triclinic, P1Z = 1
a = 3.772 (2) ÅMo Kα radiation
b = 6.322 (5) ŵ = 0.11 mm−1
c = 12.692 (3) ÅT = 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)
Tmin = 0.962, Tmax = 0.971Rint = 0.017
2173 measured reflectionsθmax = 29.0°
Refinement top
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.100Δρmax = 0.19 e Å−3
S = 0.86Δρmin = −0.19 e Å−3
1351 reflectionsAbsolute structure: ?
91 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
C10.0410 (4)−0.0391 (3)0.23081 (12)0.0356 (4)
H1−0.0514−0.17670.24500.043*
C20.1284 (4)0.0608 (3)0.31492 (12)0.0343 (4)
H20.0924−0.00900.38550.041*
C30.2692 (4)0.2646 (2)0.29319 (11)0.0292 (4)
C40.3691 (4)0.3697 (2)0.38301 (12)0.0315 (4)
C50.3203 (4)0.3700 (2)0.18790 (12)0.0337 (4)
H50.41470.50700.17380.040*
C60.2312 (4)0.2720 (3)0.10404 (12)0.0355 (4)
H60.26400.34260.03340.043*
C70.0913 (4)0.0659 (2)0.12647 (12)0.0315 (4)
N1−0.0103 (4)−0.0518 (2)0.04644 (9)0.0372 (4)
O10.2870 (4)0.2717 (2)0.47782 (9)0.0545 (4)
H1A0.35240.34170.52170.082*
O20.5255 (3)0.54435 (18)0.36449 (9)0.0453 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0452 (10)0.0306 (9)0.0329 (9)−0.0099 (7)−0.0026 (7)−0.0095 (7)
C20.0438 (10)0.0360 (9)0.0243 (8)−0.0081 (8)−0.0014 (7)−0.0072 (7)
C30.0321 (9)0.0322 (8)0.0261 (8)−0.0037 (7)−0.0030 (6)−0.0115 (7)
C40.0377 (9)0.0334 (9)0.0253 (8)−0.0060 (7)−0.0040 (6)−0.0092 (7)
C50.0436 (10)0.0295 (8)0.0299 (9)−0.0082 (7)−0.0009 (7)−0.0092 (7)
C60.0465 (10)0.0376 (9)0.0240 (8)−0.0067 (7)−0.0030 (7)−0.0084 (7)
C70.0333 (9)0.0349 (9)0.0299 (9)−0.0023 (7)−0.0048 (7)−0.0144 (7)
N10.0471 (8)0.0382 (8)0.0300 (7)−0.0081 (7)−0.0058 (7)−0.0143 (6)
O10.0875 (10)0.0544 (8)0.0254 (6)−0.0314 (7)−0.0023 (6)−0.0128 (6)
O20.0674 (8)0.0397 (7)0.0321 (7)−0.0215 (6)−0.0027 (6)−0.0119 (5)
Geometric parameters (Å, °) top
C1—C71.377 (2)C4—O11.2800 (18)
C1—C21.389 (2)C5—C61.381 (2)
C1—H10.9300C5—H50.9300
C2—C31.384 (2)C6—C71.396 (2)
C2—H20.9300C6—H60.9300
C3—C51.388 (2)C7—N11.4327 (19)
C3—C41.485 (2)N1—N1i1.239 (2)
C4—O21.246 (2)O1—H1A0.8200
C7—C1—C2119.91 (16)C6—C5—C3120.22 (15)
C7—C1—H1120.0C6—C5—H5119.9
C2—C1—H1120.0C3—C5—H5119.9
C3—C2—C1119.70 (15)C5—C6—C7119.22 (15)
C3—C2—H2120.2C5—C6—H6120.4
C1—C2—H2120.2C7—C6—H6120.4
C2—C3—C5120.28 (14)C1—C7—C6120.67 (14)
C2—C3—C4119.73 (14)C1—C7—N1115.05 (15)
C5—C3—C4119.99 (15)C6—C7—N1124.28 (14)
O2—C4—O1123.10 (14)N1i—N1—C7114.04 (17)
O2—C4—C3120.27 (14)C4—O1—H1A109.5
O1—C4—C3116.63 (15)
Symmetry codes: (i) −x, −y, −z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O2ii0.821.812.6181 (17)170
Symmetry codes: (ii) −x+1, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O2i0.821.812.6181 (17)170
Symmetry codes: (i) −x+1, −y+1, −z+1.
Acknowledgements top

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

references
References top

Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

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.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.