N,N'-Di-hydroxy-benzene-1,2:4,5-tetra-carboximide dihydrate.

In the title compound, C10H4N2O6·2H2O, the organic mol-ecule has crystallographically imposed inversion symmetry. The atoms of the three fused rings of the mol-ecule are coplanar within 0.0246 (8) Å, while the two hy-droxy O atoms are displaced from the mean plane of the mol-ecule by 0.127 (1) Å. In the crystal, infinite near-planar layers of close-packed mol-ecules are formed by hydrogen bonding between water O-H donor groups and carbonyl O-atom acceptors, and by weak inter-actions between C-H donor groups and water O-atom acceptors. The layers are parallel to the {102} family of planes. The stacked planes are held together by hydrogen bonding between N-OH donor groups and water O-atom acceptors.

Related literature

For semiconductor, optoelectronic and piezoelectric materials containing heterocycles, see: Centore, Ricciotti et al. (2012 ▶); Centore, Concilio et al. (2012 ▶). For the structural analysis of conjugation in organic mol­ecules containing heterocycles, see: Carella et al. (2004 ▶). For the crystal packing of heterocycles containing nitro­gen, see: Centore et al. (2013a ▶,b ▶). For the crystal engineering of structures containing stacked infinite planar layers, see: Centore, Causà et al. (2013 ▶). For the principle of close packing in organic crystallography, see: Kitaigorodskii (1961 ▶).

Experimental

Crystal data

C10H4N2O6·n class="Chemical">2H2O

M = 284.18

Monoclinic,

a = 6.874 (3) Å

b = 10.189 (5) Å

c = 8.099 (4) Å

β = 106.58 (2)°

V = 543.7 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.15 mm−1

T = 293 K

0.40 × 0.40 × 0.30 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.941, T max = 0.955

4484 measured reflections

1231 independent reflections

1100 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.100

S = 1.09

1231 reflections

100 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.25 e Å−3

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000 ▶); data reduction: EVALCCD (Duisenberg et al., 2003 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813016991/rz5073sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016991/rz5073Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813016991/rz5073Isup3.cml

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

C10H4N2O6·2H2O	F(000) = 292
Mr = 284.18	Dx = 1.736 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 150 reflections
a = 6.874 (3) Å	θ = 4.9–23.6°
b = 10.189 (5) Å	µ = 0.15 mm−1
c = 8.099 (4) Å	T = 293 K
β = 106.58 (2)°	Prism, yellow
V = 543.7 (4) Å3	0.40 × 0.40 × 0.30 mm
Z = 2

Bruker–Nonius KappaCCD diffractometer	1231 independent reflections
Radiation source: normal-focus sealed tube	1100 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 3.1°
CCD rotation images, thick slices scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −11→13
Tmin = 0.941, Tmax = 0.955	l = −10→9
4484 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0519P)2 + 0.137P] where P = (Fo2 + 2Fc2)/3
1231 reflections	(Δ/σ)max < 0.001
100 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.25 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	0.10245 (17)	0.10697 (12)	−0.05619 (15)	0.0244 (3)
H1	0.1688	0.1760	−0.0924	0.029*
C2	−0.05331 (17)	0.12613 (11)	0.01756 (15)	0.0230 (3)
C3	−0.15149 (15)	0.02254 (11)	0.07171 (14)	0.0230 (3)
C4	−0.31036 (17)	0.07755 (12)	0.14333 (15)	0.0254 (3)
C5	−0.14618 (17)	0.25083 (12)	0.05285 (15)	0.0258 (3)
N1	−0.29927 (15)	0.21147 (11)	0.12231 (14)	0.0287 (3)
O1	−0.42607 (13)	0.02174 (10)	0.20623 (12)	0.0346 (3)
O2	−0.10464 (15)	0.36247 (8)	0.02877 (13)	0.0360 (3)
O3	−0.40708 (15)	0.29756 (10)	0.19205 (13)	0.0367 (3)
H3	−0.499 (3)	0.3314 (17)	0.103 (2)	0.044*
O4	0.32117 (15)	0.38853 (10)	−0.08642 (14)	0.0367 (3)
H4A	0.249 (2)	0.4570 (19)	−0.067 (2)	0.044*
H4B	0.387 (3)	0.4151 (18)	−0.163 (2)	0.044*

	U11	U22	U33	U12	U13	U23
C1	0.0234 (5)	0.0230 (6)	0.0280 (6)	−0.0016 (4)	0.0092 (4)	0.0017 (5)
C2	0.0226 (5)	0.0207 (5)	0.0255 (5)	0.0009 (4)	0.0063 (4)	0.0001 (4)
C3	0.0198 (5)	0.0255 (6)	0.0246 (5)	0.0000 (4)	0.0077 (4)	−0.0006 (4)
C4	0.0231 (5)	0.0285 (6)	0.0248 (5)	0.0012 (4)	0.0074 (4)	−0.0019 (4)
C5	0.0268 (6)	0.0245 (6)	0.0258 (5)	0.0030 (4)	0.0072 (4)	−0.0003 (5)
N1	0.0303 (5)	0.0264 (6)	0.0335 (5)	0.0068 (4)	0.0156 (4)	−0.0007 (4)
O1	0.0314 (5)	0.0382 (6)	0.0405 (5)	−0.0032 (4)	0.0202 (4)	−0.0014 (4)
O2	0.0436 (6)	0.0221 (5)	0.0451 (6)	0.0019 (4)	0.0170 (5)	0.0012 (4)
O3	0.0383 (5)	0.0379 (6)	0.0369 (5)	0.0155 (4)	0.0157 (4)	−0.0047 (4)
O4	0.0379 (5)	0.0324 (5)	0.0436 (6)	0.0011 (4)	0.0178 (4)	0.0028 (4)

C1—C3i	1.3766 (17)	C4—N1	1.3799 (18)
C1—C2	1.3806 (17)	C5—O2	1.2022 (16)
C1—H1	0.9300	C5—N1	1.3866 (16)
C2—C3	1.3895 (16)	N1—O3	1.3699 (13)
C2—C5	1.4858 (16)	O3—H3	0.886 (19)
C3—C1i	1.3766 (17)	O4—H4A	0.896 (19)
C3—C4	1.4848 (16)	O4—H4B	0.909 (19)
C4—O1	1.2028 (15)
C3i—C1—C2	114.54 (11)	O1—C4—C3	129.49 (12)
C3i—C1—H1	122.7	N1—C4—C3	104.62 (10)
C2—C1—H1	122.7	O2—C5—N1	125.62 (11)
C1—C2—C3	122.39 (11)	O2—C5—C2	130.01 (11)
C1—C2—C5	129.26 (11)	N1—C5—C2	104.37 (10)
C3—C2—C5	108.35 (11)	O3—N1—C4	121.80 (10)
C1i—C3—C2	123.07 (11)	O3—N1—C5	123.00 (11)
C1i—C3—C4	128.62 (11)	C4—N1—C5	114.27 (10)
C2—C3—C4	108.31 (11)	N1—O3—H3	105.0 (11)
O1—C4—N1	125.88 (11)	H4A—O4—H4B	107.4 (16)
C3i—C1—C2—C3	0.13 (18)	C3—C2—C5—O2	178.61 (12)
C3i—C1—C2—C5	−179.51 (11)	C1—C2—C5—N1	178.07 (11)
C1—C2—C3—C1i	−0.1 (2)	C3—C2—C5—N1	−1.61 (13)
C5—C2—C3—C1i	179.57 (10)	O1—C4—N1—O3	8.09 (19)
C1—C2—C3—C4	−179.69 (10)	C3—C4—N1—O3	−172.06 (10)
C5—C2—C3—C4	0.02 (12)	O1—C4—N1—C5	177.34 (11)
C1i—C3—C4—O1	1.9 (2)	C3—C4—N1—C5	−2.80 (13)
C2—C3—C4—O1	−178.56 (12)	O2—C5—N1—O3	−8.29 (19)
C1i—C3—C4—N1	−177.92 (11)	C2—C5—N1—O3	171.92 (10)
C2—C3—C4—N1	1.59 (12)	O2—C5—N1—C4	−177.40 (12)
C1—C2—C5—O2	−1.7 (2)	C2—C5—N1—C4	2.81 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4ii	0.886 (19)	1.768 (19)	2.6516 (18)	175.2 (17)
O4—H4A···O2iii	0.896 (19)	2.15 (2)	3.0441 (17)	172.4 (16)
O4—H4B···O1iv	0.909 (19)	1.990 (19)	2.8879 (16)	169.3 (15)
C1—H1···O4	0.93	2.40	3.280 (2)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4i	0.886 (19)	1.768 (19)	2.6516 (18)	175.2 (17)
O4—H4A⋯O2ii	0.896 (19)	2.15 (2)	3.0441 (17)	172.4 (16)
O4—H4B⋯O1iii	0.909 (19)	1.990 (19)	2.8879 (16)	169.3 (15)
C1—H1⋯O4	0.93	2.40	3.280 (2)	158

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