1,4-Dihydro-quinoxaline-2,3-dione-5-nitro-isophthalic acid-water (1/1/1).

The asymmetric unit of the title compound, C(8)H(6)N(2)O(2)·C(8)H(5)NO(6)·H(2)O, contains mol-ecules of 1,4-dihydro-quinoxaline-2,3-dione, 5-nitro-isophthalic acid and a solvent water. In the crystal structure, mol-ecules are linked into a three-dimensional network by inter-molecular N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For applications of piperazine and its derivatives, see: Jian & Zhao (2004 ▶); Oxtoby et al. (2005 ▶). For uses of 5-nitro­isophthalate and its derivatives, see: He et al. (2004 ▶); Wang et al. (2009 ▶); Xu et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H6N2O2·C8H5NO6·H2O

M = 391.29

Triclinic,

a = 7.245 (2) Å

b = 8.686 (3) Å

c = 13.142 (4) Å

α = 93.938 (4)°

β = 95.619 (4)°

γ = 95.793 (4)°

V = 816.3 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 295 K

0.20 × 0.16 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.974, T max = 0.987

4482 measured reflections

2857 independent reflections

2441 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.095

S = 1.03

2857 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶) and APEX2; data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811020873/cv5099sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020873/cv5099Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811020873/cv5099Isup3.cml

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

C8H6N2O2·C8H5NO6·H2O	Z = 2
Mr = 391.29	F(000) = 404
Triclinic, P1	Dx = 1.592 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.245 (2) Å	Cell parameters from 2442 reflections
b = 8.686 (3) Å	θ = 2.4–28.2°
c = 13.142 (4) Å	µ = 0.13 mm−1
α = 93.938 (4)°	T = 295 K
β = 95.619 (4)°	Block, orange
γ = 95.793 (4)°	0.20 × 0.16 × 0.10 mm
V = 816.3 (4) Å3

Bruker APEXII CCD diffractometer	2857 independent reflections
Radiation source: fine-focus sealed tube	2441 reflections with I > 2σ(I)
graphite	Rint = 0.017
φ and ω scans	θmax = 25.1°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
Tmin = 0.974, Tmax = 0.987	k = −9→10
4482 measured reflections	l = −15→15

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)] = 0.033	H-atom parameters constrained
wR(F2) = 0.095	w = 1/[σ2(Fo2) + (0.0491P)2 + 0.199P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2857 reflections	Δρmax = 0.18 e Å−3
254 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.040 (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
N1	0.71730 (16)	0.01395 (14)	0.43192 (9)	0.0305 (3)
H1	0.6421	−0.0558	0.4543	0.037*
N2	0.96136 (17)	0.23142 (14)	0.36451 (9)	0.0322 (3)
H2	1.0403	0.2993	0.3431	0.039*
N3	0.86203 (18)	0.59454 (17)	−0.10289 (9)	0.0406 (3)
O1	0.53849 (14)	0.20004 (12)	0.47998 (8)	0.0398 (3)
O2	0.79757 (16)	0.42195 (12)	0.42271 (8)	0.0412 (3)
O3	0.54289 (17)	0.39843 (12)	0.20331 (9)	0.0467 (3)
O4	0.49185 (15)	0.61637 (12)	0.28917 (8)	0.0383 (3)
H4A	0.4479	0.5555	0.3277	0.058*
O5	0.85764 (19)	0.45403 (16)	−0.11072 (9)	0.0569 (4)
O6	0.9246 (2)	0.67836 (17)	−0.16454 (10)	0.0640 (4)
O7	0.7393 (2)	1.14774 (14)	0.02107 (10)	0.0599 (4)
O8	0.62819 (19)	1.11218 (13)	0.17111 (9)	0.0538 (3)
H8	0.6236	1.2062	0.1725	0.081*
O9	0.32657 (14)	0.43362 (12)	0.40853 (8)	0.0369 (3)
H9A	0.4013	0.3730	0.4352	0.055*
H9B	0.3007	0.4804	0.4643	0.055*
C1	0.67867 (19)	0.16099 (17)	0.44281 (10)	0.0293 (3)
C2	0.8180 (2)	0.28385 (17)	0.40886 (10)	0.0296 (3)
C3	0.9929 (2)	0.07624 (17)	0.35027 (10)	0.0299 (3)
C4	1.1426 (2)	0.0307 (2)	0.30139 (12)	0.0417 (4)
H4	1.2255	0.1047	0.2770	0.050*
C5	1.1677 (2)	−0.1238 (2)	0.28923 (13)	0.0481 (4)
H5	1.2657	−0.1545	0.2547	0.058*
C6	1.0477 (2)	−0.2347 (2)	0.32807 (12)	0.0436 (4)
H6	1.0674	−0.3389	0.3208	0.052*
C7	0.8999 (2)	−0.19105 (18)	0.37722 (11)	0.0346 (3)
H7	0.8201	−0.2652	0.4037	0.042*
C8	0.87052 (19)	−0.03525 (16)	0.38704 (10)	0.0280 (3)
C9	0.63865 (19)	0.64015 (17)	0.13886 (10)	0.0296 (3)
C10	0.7140 (2)	0.57178 (18)	0.05592 (10)	0.0324 (3)
H10	0.7161	0.4648	0.0475	0.039*
C11	0.7857 (2)	0.66751 (18)	−0.01360 (10)	0.0334 (3)
C12	0.7849 (2)	0.82652 (19)	−0.00467 (11)	0.0366 (4)
H12	0.8342	0.8876	−0.0530	0.044*
C13	0.7085 (2)	0.89318 (18)	0.07831 (11)	0.0334 (3)
C14	0.6363 (2)	0.79974 (17)	0.14970 (10)	0.0318 (3)
H14	0.5858	0.8448	0.2054	0.038*
C15	0.5552 (2)	0.53871 (17)	0.21328 (10)	0.0312 (3)
C16	0.6963 (2)	1.06385 (19)	0.08583 (12)	0.0394 (4)

	U11	U22	U33	U12	U13	U23
N1	0.0280 (6)	0.0267 (6)	0.0384 (6)	−0.0004 (5)	0.0113 (5)	0.0073 (5)
N2	0.0322 (7)	0.0281 (7)	0.0385 (6)	−0.0004 (5)	0.0157 (5)	0.0061 (5)
N3	0.0386 (7)	0.0518 (9)	0.0324 (7)	0.0076 (7)	0.0079 (5)	0.0010 (6)
O1	0.0335 (6)	0.0351 (6)	0.0562 (7)	0.0079 (5)	0.0223 (5)	0.0112 (5)
O2	0.0493 (7)	0.0261 (6)	0.0520 (6)	0.0059 (5)	0.0213 (5)	0.0047 (5)
O3	0.0666 (8)	0.0256 (6)	0.0507 (7)	0.0053 (5)	0.0202 (6)	0.0022 (5)
O4	0.0488 (7)	0.0299 (6)	0.0394 (6)	0.0045 (5)	0.0195 (5)	0.0032 (4)
O5	0.0747 (9)	0.0491 (8)	0.0510 (7)	0.0162 (7)	0.0232 (6)	−0.0055 (6)
O6	0.0832 (10)	0.0687 (9)	0.0458 (7)	0.0048 (8)	0.0337 (7)	0.0107 (7)
O7	0.0803 (10)	0.0387 (7)	0.0648 (8)	0.0053 (7)	0.0193 (7)	0.0181 (6)
O8	0.0816 (9)	0.0283 (6)	0.0547 (7)	0.0125 (6)	0.0166 (6)	0.0037 (5)
O9	0.0390 (6)	0.0332 (6)	0.0405 (6)	0.0059 (5)	0.0122 (4)	0.0037 (4)
C1	0.0286 (7)	0.0300 (8)	0.0309 (7)	0.0042 (6)	0.0081 (6)	0.0049 (6)
C2	0.0324 (8)	0.0289 (8)	0.0288 (7)	0.0032 (6)	0.0089 (5)	0.0038 (6)
C3	0.0314 (8)	0.0296 (8)	0.0298 (7)	0.0044 (6)	0.0069 (6)	0.0026 (6)
C4	0.0372 (9)	0.0455 (10)	0.0463 (9)	0.0079 (7)	0.0177 (7)	0.0080 (7)
C5	0.0454 (10)	0.0500 (11)	0.0550 (10)	0.0196 (8)	0.0217 (8)	0.0039 (8)
C6	0.0488 (10)	0.0343 (9)	0.0491 (9)	0.0145 (8)	0.0049 (7)	−0.0012 (7)
C7	0.0359 (8)	0.0295 (8)	0.0381 (7)	0.0023 (6)	0.0026 (6)	0.0038 (6)
C8	0.0278 (7)	0.0294 (8)	0.0270 (6)	0.0033 (6)	0.0038 (5)	0.0015 (6)
C9	0.0293 (7)	0.0292 (8)	0.0304 (7)	0.0040 (6)	0.0036 (5)	0.0005 (6)
C10	0.0327 (8)	0.0307 (8)	0.0338 (7)	0.0047 (6)	0.0040 (6)	0.0001 (6)
C11	0.0315 (8)	0.0390 (9)	0.0299 (7)	0.0049 (7)	0.0055 (6)	−0.0008 (6)
C12	0.0348 (8)	0.0405 (9)	0.0352 (7)	0.0015 (7)	0.0057 (6)	0.0094 (7)
C13	0.0315 (8)	0.0317 (8)	0.0363 (7)	0.0023 (6)	0.0010 (6)	0.0036 (6)
C14	0.0325 (8)	0.0318 (8)	0.0313 (7)	0.0049 (6)	0.0047 (6)	0.0004 (6)
C15	0.0332 (8)	0.0281 (8)	0.0328 (7)	0.0056 (6)	0.0051 (6)	0.0003 (6)
C16	0.0402 (9)	0.0320 (9)	0.0455 (9)	0.0020 (7)	0.0018 (7)	0.0060 (7)

N1—C1	1.3360 (18)	C3—C4	1.391 (2)
N1—C8	1.3972 (17)	C4—C5	1.373 (2)
N1—H1	0.8600	C4—H4	0.9300
N2—C2	1.3428 (17)	C5—C6	1.389 (3)
N2—C3	1.3928 (19)	C5—H5	0.9300
N2—H2	0.8600	C6—C7	1.376 (2)
N3—O5	1.2147 (19)	C6—H6	0.9300
N3—O6	1.2158 (18)	C7—C8	1.390 (2)
N3—C11	1.4764 (18)	C7—H7	0.9300
O1—C1	1.2365 (16)	C9—C14	1.386 (2)
O2—C2	1.2268 (18)	C9—C10	1.3900 (19)
O3—C15	1.2098 (18)	C9—C15	1.492 (2)
O4—C15	1.3114 (16)	C10—C11	1.381 (2)
O4—H4A	0.8200	C10—H10	0.9300
O7—C16	1.201 (2)	C11—C12	1.379 (2)
O8—C16	1.327 (2)	C12—C13	1.388 (2)
O8—H8	0.8200	C12—H12	0.9300
O9—H9A	0.8597	C13—C14	1.388 (2)
O9—H9B	0.8598	C13—C16	1.491 (2)
C1—C2	1.514 (2)	C14—H14	0.9300
C3—C8	1.390 (2)
C1—N1—C8	125.04 (12)	C6—C7—C8	119.52 (15)
C1—N1—H1	117.5	C6—C7—H7	120.2
C8—N1—H1	117.5	C8—C7—H7	120.2
C2—N2—C3	125.43 (12)	C3—C8—C7	120.28 (13)
C2—N2—H2	117.3	C3—C8—N1	118.07 (12)
C3—N2—H2	117.3	C7—C8—N1	121.64 (13)
O5—N3—O6	123.82 (13)	C14—C9—C10	120.07 (13)
O5—N3—C11	118.00 (13)	C14—C9—C15	120.96 (12)
O6—N3—C11	118.17 (14)	C10—C9—C15	118.95 (13)
C15—O4—H4A	109.5	C11—C10—C9	117.97 (14)
C16—O8—H8	109.5	C11—C10—H10	121.0
H9A—O9—H9B	98.3	C9—C10—H10	121.0
O1—C1—N1	123.40 (13)	C12—C11—C10	123.11 (13)
O1—C1—C2	119.59 (13)	C12—C11—N3	118.92 (13)
N1—C1—C2	117.01 (12)	C10—C11—N3	117.95 (14)
O2—C2—N2	123.62 (14)	C11—C12—C13	118.30 (14)
O2—C2—C1	120.46 (12)	C11—C12—H12	120.8
N2—C2—C1	115.92 (12)	C13—C12—H12	120.8
C8—C3—C4	119.61 (14)	C12—C13—C14	119.81 (14)
C8—C3—N2	118.35 (12)	C12—C13—C16	118.98 (14)
C4—C3—N2	122.04 (14)	C14—C13—C16	121.12 (13)
C5—C4—C3	119.81 (16)	C9—C14—C13	120.74 (13)
C5—C4—H4	120.1	C9—C14—H14	119.6
C3—C4—H4	120.1	C13—C14—H14	119.6
C4—C5—C6	120.48 (14)	O3—C15—O4	123.24 (14)
C4—C5—H5	119.8	O3—C15—C9	123.34 (13)
C6—C5—H5	119.8	O4—C15—C9	113.40 (12)
C7—C6—C5	120.25 (15)	O7—C16—O8	123.72 (15)
C7—C6—H6	119.9	O7—C16—C13	123.92 (15)
C5—C6—H6	119.9	O8—C16—C13	112.33 (13)
C8—N1—C1—O1	177.60 (13)	C15—C9—C10—C11	178.18 (12)
C8—N1—C1—C2	−3.47 (19)	C9—C10—C11—C12	−0.3 (2)
C3—N2—C2—O2	177.86 (13)	C9—C10—C11—N3	−178.69 (12)
C3—N2—C2—C1	−1.7 (2)	O5—N3—C11—C12	−178.32 (14)
O1—C1—C2—O2	3.7 (2)	O6—N3—C11—C12	1.3 (2)
N1—C1—C2—O2	−175.29 (13)	O5—N3—C11—C10	0.1 (2)
O1—C1—C2—N2	−176.70 (13)	O6—N3—C11—C10	179.69 (14)
N1—C1—C2—N2	4.33 (18)	C10—C11—C12—C13	0.1 (2)
C2—N2—C3—C8	−1.9 (2)	N3—C11—C12—C13	178.43 (13)
C2—N2—C3—C4	178.47 (14)	C11—C12—C13—C14	0.2 (2)
C8—C3—C4—C5	0.4 (2)	C11—C12—C13—C16	−176.43 (13)
N2—C3—C4—C5	180.00 (14)	C10—C9—C14—C13	0.1 (2)
C3—C4—C5—C6	−1.9 (3)	C15—C9—C14—C13	−177.81 (12)
C4—C5—C6—C7	1.4 (3)	C12—C13—C14—C9	−0.3 (2)
C5—C6—C7—C8	0.5 (2)	C16—C13—C14—C9	176.26 (13)
C4—C3—C8—C7	1.5 (2)	C14—C9—C15—O3	174.98 (14)
N2—C3—C8—C7	−178.08 (12)	C10—C9—C15—O3	−2.9 (2)
C4—C3—C8—N1	−177.39 (13)	C14—C9—C15—O4	−3.3 (2)
N2—C3—C8—N1	3.02 (19)	C10—C9—C15—O4	178.79 (12)
C6—C7—C8—C3	−2.0 (2)	C12—C13—C16—O7	4.3 (2)
C6—C7—C8—N1	176.89 (13)	C14—C13—C16—O7	−172.28 (16)
C1—N1—C8—C3	−0.2 (2)	C12—C13—C16—O8	−177.21 (14)
C1—N1—C8—C7	−179.10 (13)	C14—C13—C16—O8	6.2 (2)
C14—C9—C10—C11	0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O6i	0.86	2.40	2.9632 (18)	123.
N2—H2···O9ii	0.86	2.33	3.0071 (17)	136.
N1—H1···O1iii	0.86	2.02	2.8723 (17)	173.
O9—H9B···O2iv	0.86	1.89	2.7456 (15)	171.
O8—H8···O3v	0.82	1.86	2.6381 (17)	159.
O9—H9A···O1	0.86	1.97	2.8220 (15)	168.
O4—H4A···O9	0.82	1.78	2.5962 (15)	173.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O6i	0.86	2.40	2.9632 (18)	123
N2—H2⋯O9ii	0.86	2.33	3.0071 (17)	136
N1—H1⋯O1iii	0.86	2.02	2.8723 (17)	173
O9—H9B⋯O2iv	0.86	1.89	2.7456 (15)	171
O8—H8⋯O3v	0.82	1.86	2.6381 (17)	159
O9—H9A⋯O1	0.86	1.97	2.8220 (15)	168
O4—H4A⋯O9	0.82	1.78	2.5962 (15)	173

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