3,3'-Diazenediyldiphthalic acid dihydrate.

In the crystal structure of the title compound, C(16)H(10)N(2)O(8)·2H(2)O, the organic mol-ecule is located on a centre of symmetry. The two benzene rings are parallel, but not coplanar, as indicated by N=N-C-C torsion angles involving the azo group of 12.1 (5) and -168.2 (3)°. The organic mol-ecule and the water mol-ecule are linked by O-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For related literature, see: Carlucci et al. (2000 ▶).

Experimental

Crystal data

C16H10N2O8·2H2O

M = 394.29

Triclinic,

a = 6.6914 (14) Å

b = 7.8566 (17) Å

c = 8.7665 (19) Å

α = 95.658 (3)°

β = 100.628 (3)°

γ = 105.601 (3)°

V = 430.90 (16) Å3

Z = 1

Mo Kα radiation

μ = 0.13 mm−1

T = 298 (2) K

0.27 × 0.19 × 0.15 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (; Sheldrick, 2004 ▶) T min = 0.966, T max = 0.981

2297 measured reflections

1530 independent reflections

1248 reflections with I > 2σ(I)

R int = 0.009

Refinement

R[F 2 > 2σ(F 2)] = 0.084

wR(F 2) = 0.260

S = 1.11

1530 reflections

135 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.04 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807064112/is2247sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064112/is2247Isup2.hkl

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

C16H10N2O8·2H2O	Z = 1
Mr = 394.29	F000 = 204
Triclinic, P1	Dx = 1.519 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 6.6914 (14) Å	Cell parameters from 1248 reflections
b = 7.8566 (17) Å	θ = 2.4–25.2º
c = 8.7665 (19) Å	µ = 0.13 mm−1
α = 95.658 (3)º	T = 298 (2) K
β = 100.628 (3)º	Block, colourless
γ = 105.601 (3)º	0.27 × 0.19 × 0.15 mm
V = 430.90 (16) Å3

Bruker APEXII area-detector diffractometer	1530 independent reflections
Radiation source: fine-focus sealed tube	1248 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.009
T = 298(2) K	θmax = 25.2º
φ and ω scan	θmin = 2.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)	h = −7→8
Tmin = 0.966, Tmax = 0.981	k = −6→9
2297 measured reflections	l = −10→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.084	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.260	w = 1/[σ2(Fo2) + (0.16P)2 + 0.1722P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
1530 reflections	Δρmax = 1.04 e Å−3
135 parameters	Δρmin = −0.19 e Å−3
3 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	0.1413 (5)	0.2366 (4)	0.1954 (4)	0.0537 (8)
C2	0.0818 (5)	0.2502 (4)	0.3535 (3)	0.0505 (8)
C3	−0.1122 (5)	0.1482 (4)	0.3774 (4)	0.0541 (8)
C4	−0.2663 (5)	0.0169 (4)	0.2462 (4)	0.0558 (8)
C5	−0.1571 (6)	0.1709 (5)	0.5259 (4)	0.0688 (10)
H5	−0.2867	0.1042	0.5425	0.083*
C6	−0.0133 (7)	0.2900 (6)	0.6479 (4)	0.0775 (11)
H6	−0.0472	0.3046	0.7457	0.093*
C7	0.1814 (7)	0.3884 (5)	0.6264 (4)	0.0741 (11)
H7	0.2792	0.4681	0.7095	0.089*
C8	0.2295 (5)	0.3672 (4)	0.4798 (4)	0.0585 (9)
N1	0.4269 (5)	0.4597 (4)	0.4434 (3)	0.0664 (9)
O1	0.1017 (4)	0.3301 (3)	0.1000 (3)	0.0728 (8)
O2	0.2414 (5)	0.1183 (4)	0.1782 (3)	0.0797 (9)
H2	0.2913	0.1285	0.0997	0.120*
O3	−0.2418 (5)	0.0128 (4)	0.1130 (3)	0.0933 (11)
O4	−0.4243 (4)	−0.0911 (4)	0.2846 (3)	0.0759 (8)
H4	−0.4939	−0.1658	0.2080	0.114*
O1W	0.3401 (5)	0.6712 (4)	0.0411 (4)	0.0934 (10)
H1WA	0.306 (7)	0.563 (3)	0.057 (8)	0.140*
H1WB	0.228 (5)	0.705 (6)	0.025 (8)	0.140*

	U11	U22	U33	U12	U13	U23
C1	0.0446 (15)	0.0528 (17)	0.0533 (17)	0.0005 (13)	0.0063 (12)	0.0074 (14)
C2	0.0540 (16)	0.0461 (15)	0.0499 (16)	0.0139 (13)	0.0078 (13)	0.0087 (12)
C3	0.0584 (18)	0.0510 (17)	0.0584 (18)	0.0205 (14)	0.0168 (14)	0.0137 (13)
C4	0.0509 (17)	0.0527 (17)	0.0627 (19)	0.0066 (14)	0.0185 (14)	0.0165 (14)
C5	0.078 (2)	0.075 (2)	0.070 (2)	0.0326 (19)	0.0336 (18)	0.0233 (18)
C6	0.101 (3)	0.085 (3)	0.056 (2)	0.038 (2)	0.028 (2)	0.0067 (18)
C7	0.096 (3)	0.070 (2)	0.0527 (19)	0.031 (2)	0.0049 (17)	−0.0023 (16)
C8	0.0645 (19)	0.0506 (17)	0.0566 (18)	0.0164 (15)	0.0064 (14)	0.0045 (13)
N1	0.0659 (18)	0.0644 (17)	0.0545 (16)	0.0066 (14)	0.0004 (12)	0.0012 (12)
O1	0.0810 (17)	0.0723 (16)	0.0667 (15)	0.0140 (13)	0.0225 (12)	0.0301 (13)
O2	0.100 (2)	0.100 (2)	0.0593 (15)	0.0501 (17)	0.0301 (13)	0.0201 (13)
O3	0.0813 (18)	0.093 (2)	0.0686 (18)	−0.0311 (15)	0.0182 (13)	−0.0046 (14)
O4	0.0589 (15)	0.0733 (17)	0.0910 (19)	0.0041 (12)	0.0260 (13)	0.0159 (13)
O1W	0.0775 (19)	0.0712 (18)	0.116 (2)	0.0007 (14)	0.0076 (17)	0.0286 (17)

C1—O1	1.205 (4)	C6—C7	1.381 (5)
C1—O2	1.296 (4)	C6—H6	0.9300
C1—C2	1.513 (4)	C7—C8	1.387 (5)
C2—C3	1.395 (4)	C7—H7	0.9300
C2—C8	1.398 (4)	C8—N1	1.435 (5)
C3—C5	1.394 (5)	N1—N1i	1.236 (5)
C3—C4	1.486 (5)	O2—H2	0.8200
C4—O3	1.207 (4)	O4—H4	0.8200
C4—O4	1.287 (4)	O1W—H1WA	0.85 (3)
C5—C6	1.373 (6)	O1W—H1WB	0.85 (4)
C5—H5	0.9300
O1—C1—O2	125.3 (3)	C3—C5—H5	119.4
O1—C1—C2	122.3 (3)	C5—C6—C7	120.4 (3)
O2—C1—C2	112.4 (3)	C5—C6—H6	119.8
C3—C2—C8	119.5 (3)	C7—C6—H6	119.8
C3—C2—C1	122.3 (3)	C6—C7—C8	119.4 (3)
C8—C2—C1	118.2 (3)	C6—C7—H7	120.3
C5—C3—C2	118.9 (3)	C8—C7—H7	120.3
C5—C3—C4	121.1 (3)	C7—C8—C2	120.7 (3)
C2—C3—C4	120.0 (3)	C7—C8—N1	124.6 (3)
O3—C4—O4	123.0 (3)	C2—C8—N1	114.7 (3)
O3—C4—C3	121.4 (3)	N1i—N1—C8	116.2 (4)
O4—C4—C3	115.6 (3)	C1—O2—H2	109.5
C6—C5—C3	121.1 (3)	C4—O4—H4	109.5
C6—C5—H5	119.4	H1WA—O1W—H1WB	109 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O1	0.85 (3)	2.08 (2)	2.875 (4)	155 (4)
O4—H4···O1Wii	0.82	1.81	2.631 (4)	177
O1W—H1WB···O3iii	0.85 (4)	2.62 (4)	3.104 (5)	117 (4)
O2—H2···O3iv	0.82	2.00	2.657 (4)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O1	0.85 (3)	2.08 (2)	2.875 (4)	155 (4)
O4—H4⋯O1Wi	0.82	1.81	2.631 (4)	177
O1W—H1WB⋯O3ii	0.85 (4)	2.62 (4)	3.104 (5)	117 (4)
O2—H2⋯O3iii	0.82	2.00	2.657 (4)	137

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