4,4'-azinodibenzoic Acid.

The title compound, C(14)H(10)N(2)O(4), shows crystallographic inversion symmetry and has one half-mol-ecule in the asymmetric unit. In the crystal, mol-ecules are linked into chains running along the cell diagonal by O-H⋯O hydrogen-bonding inter-actions.

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 = 270.16

Triclinic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.100

S = 0.86

1351 reflections

91 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.19 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809033224/bt5033sup1.cif

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

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

C14H10N2O4	Z = 1
Mr = 270.16	F(000) = 140
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0555P)2] where P = (Fo2 + 2Fc2)/3
1351 reflections	(Δ/σ)max < 0.001
91 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.19 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	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)

	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)

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)

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

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) .