2-Amino-4-nitro-phenol-1-(2,4,6-trihy-droxy-phen-yl)ethanone (1/1).

In the title compound, C(6)H(6)N(2)O(3)·C(8)H(8)O(4), the 2-amino-4-nitro-phenol (ANP) and 1-(2,4,6-trihy-droxy-phen-yl)ethanone (THA) mol-ecules are both nearly planar, with r.m.s. deviations of 0.0630 and 0.0313 Å, respectively. The angle between the least-squares planes of THA and ANP is 48.99 (2)°. In THA, an intra-molecular O-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, N-H⋯O, O-H⋯O and O-H⋯N hydrogen bonds lead to the formation of a three-dimensional network. There are also inter-molecular π-π inter-actions between the benzene rings of ANP-ANP and of THA-THA mol-ecules, with centroid-centroid distances of 3.5313 (14) and 3.8440 (16) Å, respectively. Weak C-O⋯π and N-O⋯π inter-actions also occur.

Related literature

For the use of nitro­aromatics as inter­mediates in explosives, dyestuffs, pesticides and organic synthesis, see: Yan et al. (2006 ▶). For the occurrence of nitro­aromatics in industrial wastes and as direct pollutants in the environment, see: Yan et al. (2006 ▶); Soojhawon et al. (2005 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Tanak et al. (2009 ▶, 2010 ▶); Ali et al. (2008 ▶); Bi et al. (2009 ▶); Garden et al. (2004 ▶); Serdiuk et al. (2011 ▶).

Experimental

Crystal data

C6H6N2O3·C8H8O4

M = 322.27

Monoclinic,

a = 7.7255 (6) Å

b = 13.2184 (11) Å

c = 15.8335 (12) Å

β = 118.148 (5)°

V = 1425.67 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 296 K

0.80 × 0.35 × 0.09 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED; Stoe & Cie, 2002 ▶) T min = 0.942, T max = 0.992

15333 measured reflections

2961 independent reflections

1841 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.098

S = 0.97

2961 reflections

252 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.24 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812017497/kj2199sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017497/kj2199Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812017497/kj2199Isup3.cml

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

C6H6N2O3·C8H8O4	F(000) = 672
Mr = 322.27	Dx = 1.501 Mg m−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 12619 reflections
a = 7.7255 (6) Å	θ = 2.1–27.3°
b = 13.2184 (11) Å	µ = 0.12 mm−1
c = 15.8335 (12) Å	T = 296 K
β = 118.148 (5)°	Prism, yellow
V = 1425.67 (19) Å3	0.80 × 0.35 × 0.09 mm
Z = 4

Stoe IPDS 2 diffractometer	2961 independent reflections
Radiation source: fine-focus sealed tube	1841 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 2.1°
rotation method scans	h = −9→9
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	k = −16→16
Tmin = 0.942, Tmax = 0.992	l = −19→19
15333 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ2(Fo2) + (0.0466P)2] where P = (Fo2 + 2Fc2)/3
2961 reflections	(Δ/σ)max < 0.001
252 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Experimental. IR (KBr, cm-1): 3523 ν(OH)THA, 3383 ν(NH2)asym, 3353 ν(NH2)sym+ν(OH)THA, 3298 ν(OH)THA, 3090–3000 ν(CH), 2850–2700 ν(CH3), 1628 ν(C=O)+δ(OH)THA+ν(ring)THA, 1614 ν(NH2)+ν(ring)ANP, 1571 δ(NH2), 1524 ν(NO2)asym, 1496–1476 δ(CH)+δ(OH)ANP, 1364–1339 δ(CH3)+δ(OH)THA, 1311–1251 ν(NO2)+ν(CO)ANP, 1203–1167–1147 ν(ring)+δ(OH). UV/Visible (nm): 226 (2,212 Å; ε= 19230 L mol-1cm-1) and 288 (1,815 Å; ε= 15780 L mol-1cm-1) π→π* transitions of benzene ring (E bands), 380 nm (0,345 Å; ε= 3000 L mol-1cm-1) π→π* transition of aniline (E2 band).

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	0.5977 (3)	0.40750 (14)	0.66694 (13)	0.0394 (5)
C2	0.6191 (4)	0.51128 (15)	0.67342 (16)	0.0498 (6)
C3	0.7703 (4)	0.55477 (16)	0.75249 (17)	0.0520 (6)
C4	0.8964 (3)	0.49206 (15)	0.82522 (14)	0.0456 (5)
C5	0.8776 (3)	0.38806 (15)	0.82066 (14)	0.0411 (5)
C6	0.7271 (3)	0.34480 (13)	0.74077 (13)	0.0361 (4)
C7	0.7798 (3)	0.00373 (15)	0.64563 (14)	0.0411 (5)
C8	0.7390 (3)	−0.09742 (14)	0.62254 (14)	0.0423 (5)
C9	0.7120 (3)	−0.13396 (15)	0.53533 (15)	0.0461 (5)
C10	0.7236 (3)	−0.06837 (14)	0.47110 (13)	0.0409 (5)
C11	0.7631 (3)	0.03665 (14)	0.49051 (13)	0.0380 (5)
C12	0.7933 (3)	0.06963 (14)	0.58187 (14)	0.0395 (5)
C13	0.7601 (3)	0.10280 (15)	0.41713 (15)	0.0466 (5)
C14	0.7792 (5)	0.21463 (17)	0.42704 (19)	0.0779 (9)
H14A	0.7731	0.2432	0.3700	0.117*
H14B	0.9027	0.2316	0.4810	0.117*
H14C	0.6742	0.2414	0.4365	0.117*
N1	1.0593 (3)	0.53726 (17)	0.90766 (15)	0.0622 (6)
N2	0.7059 (3)	0.23928 (13)	0.72998 (14)	0.0473 (5)
O1	1.0834 (3)	0.62880 (15)	0.91011 (15)	0.0944 (7)
O2	1.1715 (3)	0.48199 (16)	0.97227 (13)	0.0774 (6)
O3	0.4543 (3)	0.35925 (12)	0.59151 (11)	0.0571 (5)
O4	0.8398 (3)	0.16790 (11)	0.60576 (12)	0.0587 (5)
O5	0.7222 (3)	−0.16375 (12)	0.68295 (12)	0.0640 (5)
O6	0.6904 (3)	−0.10661 (12)	0.38519 (11)	0.0579 (5)
O7	0.7370 (3)	0.06669 (11)	0.33974 (10)	0.0605 (5)
H2	0.532 (3)	0.5607 (15)	0.6211 (15)	0.053 (6)*
H2A	0.764 (3)	0.2079 (17)	0.7899 (18)	0.061 (7)*
H2B	0.575 (4)	0.2194 (19)	0.692 (2)	0.078 (9)*
H3	0.790 (3)	0.6232 (17)	0.7574 (15)	0.050 (6)*
H3A	0.375 (5)	0.404 (2)	0.556 (2)	0.100 (11)*
H4	0.812 (4)	0.1827 (18)	0.6505 (19)	0.063 (8)*
H5	0.963 (3)	0.3471 (14)	0.8687 (15)	0.042 (6)*
H5A	0.734 (4)	−0.134 (2)	0.735 (2)	0.093 (10)*
H6	0.702 (4)	−0.0539 (18)	0.3500 (18)	0.067 (8)*
H7	0.802 (3)	0.0289 (14)	0.7084 (14)	0.041 (5)*
H9	0.691 (3)	−0.2043 (18)	0.5206 (16)	0.060 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0367 (12)	0.0479 (11)	0.0311 (10)	−0.0011 (9)	0.0139 (9)	−0.0043 (8)
C2	0.0508 (15)	0.0448 (12)	0.0474 (13)	0.0077 (10)	0.0178 (12)	0.0048 (10)
C3	0.0570 (16)	0.0380 (12)	0.0619 (15)	0.0002 (10)	0.0287 (13)	−0.0089 (10)
C4	0.0387 (13)	0.0540 (12)	0.0407 (11)	−0.0053 (10)	0.0161 (10)	−0.0169 (9)
C5	0.0402 (13)	0.0514 (12)	0.0298 (10)	0.0053 (10)	0.0149 (10)	−0.0007 (9)
C6	0.0402 (12)	0.0384 (10)	0.0328 (10)	0.0000 (8)	0.0199 (9)	−0.0029 (8)
C7	0.0444 (13)	0.0483 (11)	0.0307 (10)	−0.0019 (9)	0.0178 (10)	−0.0075 (8)
C8	0.0452 (14)	0.0439 (11)	0.0382 (11)	0.0033 (9)	0.0199 (10)	0.0011 (8)
C9	0.0573 (15)	0.0368 (11)	0.0455 (12)	−0.0008 (9)	0.0254 (11)	−0.0066 (9)
C10	0.0435 (13)	0.0450 (11)	0.0325 (10)	0.0013 (9)	0.0165 (9)	−0.0100 (8)
C11	0.0346 (12)	0.0460 (11)	0.0335 (10)	−0.0017 (9)	0.0163 (9)	−0.0056 (8)
C12	0.0374 (13)	0.0435 (10)	0.0381 (11)	−0.0055 (9)	0.0183 (9)	−0.0108 (8)
C13	0.0477 (14)	0.0534 (12)	0.0426 (12)	−0.0058 (10)	0.0245 (11)	−0.0056 (9)
C14	0.126 (3)	0.0560 (14)	0.0640 (17)	−0.0166 (15)	0.0552 (18)	0.0019 (12)
N1	0.0463 (14)	0.0798 (15)	0.0543 (13)	−0.0063 (11)	0.0188 (11)	−0.0278 (11)
N2	0.0591 (14)	0.0416 (10)	0.0385 (10)	−0.0016 (9)	0.0208 (10)	0.0011 (8)
O1	0.0808 (15)	0.0721 (12)	0.1081 (17)	−0.0231 (10)	0.0262 (12)	−0.0512 (11)
O2	0.0540 (12)	0.1078 (14)	0.0477 (10)	−0.0066 (11)	0.0053 (9)	−0.0182 (10)
O3	0.0502 (11)	0.0598 (10)	0.0398 (9)	−0.0014 (8)	0.0035 (8)	−0.0051 (7)
O4	0.0895 (14)	0.0454 (8)	0.0572 (10)	−0.0206 (8)	0.0477 (10)	−0.0197 (7)
O5	0.1024 (15)	0.0491 (8)	0.0503 (10)	−0.0017 (8)	0.0441 (10)	0.0014 (7)
O6	0.0865 (13)	0.0525 (9)	0.0414 (8)	−0.0089 (8)	0.0358 (9)	−0.0143 (7)
O7	0.0853 (13)	0.0634 (9)	0.0410 (8)	−0.0037 (8)	0.0366 (9)	−0.0027 (7)

C1—O3	1.346 (2)	C10—O6	1.357 (2)
C1—C2	1.380 (3)	C10—C11	1.424 (3)
C1—C6	1.396 (3)	C11—C12	1.421 (3)
C2—C3	1.372 (3)	C11—C13	1.445 (3)
C2—H2	1.02 (2)	C12—O4	1.353 (2)
C3—C4	1.380 (3)	C13—O7	1.247 (2)
C3—H3	0.91 (2)	C13—C14	1.487 (3)
C4—C5	1.381 (3)	C14—H14A	0.9600
C4—N1	1.447 (3)	C14—H14B	0.9600
C5—C6	1.375 (3)	C14—H14C	0.9600
C5—H5	0.91 (2)	N1—O1	1.222 (3)
C6—N2	1.405 (2)	N1—O2	1.222 (3)
C7—C12	1.374 (3)	N2—H2A	0.93 (3)
C7—C8	1.383 (3)	N2—H2B	0.93 (3)
C7—H7	0.98 (2)	O3—H3A	0.84 (3)
C8—O5	1.348 (2)	O4—H4	0.86 (3)
C8—C9	1.383 (3)	O5—H5A	0.88 (3)
C9—C10	1.371 (3)	O6—H6	0.92 (3)
C9—H9	0.95 (2)
O3—C1—C2	123.81 (19)	O6—C10—C11	119.96 (18)
O3—C1—C6	115.21 (17)	C9—C10—C11	122.61 (18)
C2—C1—C6	120.98 (19)	C12—C11—C10	115.75 (17)
C3—C2—C1	120.3 (2)	C12—C11—C13	124.43 (17)
C3—C2—H2	115.1 (11)	C10—C11—C13	119.73 (17)
C1—C2—H2	124.5 (11)	O4—C12—C7	120.34 (17)
C2—C3—C4	118.2 (2)	O4—C12—C11	118.28 (17)
C2—C3—H3	121.8 (13)	C7—C12—C11	121.37 (17)
C4—C3—H3	120.0 (14)	O7—C13—C11	119.92 (17)
C3—C4—C5	122.63 (19)	O7—C13—C14	116.4 (2)
C3—C4—N1	118.4 (2)	C11—C13—C14	123.62 (19)
C5—C4—N1	118.9 (2)	C13—C14—H14A	109.5
C6—C5—C4	118.97 (19)	C13—C14—H14B	109.5
C6—C5—H5	119.0 (12)	H14A—C14—H14B	109.5
C4—C5—H5	122.0 (12)	C13—C14—H14C	109.5
C5—C6—C1	118.94 (17)	H14A—C14—H14C	109.5
C5—C6—N2	121.59 (19)	H14B—C14—H14C	109.5
C1—C6—N2	119.41 (18)	O1—N1—O2	121.9 (2)
C12—C7—C8	120.37 (18)	O1—N1—C4	119.5 (2)
C12—C7—H7	119.3 (11)	O2—N1—C4	118.7 (2)
C8—C7—H7	120.3 (11)	C6—N2—H2A	110.2 (14)
O5—C8—C9	117.50 (17)	C6—N2—H2B	112.7 (16)
O5—C8—C7	121.84 (18)	H2A—N2—H2B	112 (2)
C9—C8—C7	120.66 (19)	C1—O3—H3A	107 (2)
C10—C9—C8	119.21 (18)	C12—O4—H4	108.3 (16)
C10—C9—H9	119.9 (14)	C8—O5—H5A	112.0 (19)
C8—C9—H9	120.9 (14)	C10—O6—H6	107.3 (15)
O6—C10—C9	117.41 (17)
O3—C1—C2—C3	−179.5 (2)	O6—C10—C11—C12	179.20 (18)
C6—C1—C2—C3	0.9 (4)	C9—C10—C11—C12	1.0 (3)
C1—C2—C3—C4	−1.2 (4)	O6—C10—C11—C13	2.4 (3)
C2—C3—C4—C5	0.9 (3)	C9—C10—C11—C13	−175.8 (2)
C2—C3—C4—N1	178.3 (2)	C8—C7—C12—O4	−177.8 (2)
C3—C4—C5—C6	−0.2 (3)	C8—C7—C12—C11	1.0 (3)
N1—C4—C5—C6	−177.64 (19)	C10—C11—C12—O4	177.22 (19)
C4—C5—C6—C1	−0.2 (3)	C13—C11—C12—O4	−6.2 (3)
C4—C5—C6—N2	177.0 (2)	C10—C11—C12—C7	−1.6 (3)
O3—C1—C6—C5	−179.80 (19)	C13—C11—C12—C7	175.0 (2)
C2—C1—C6—C5	−0.1 (3)	C12—C11—C13—O7	178.3 (2)
O3—C1—C6—N2	3.0 (3)	C10—C11—C13—O7	−5.2 (3)
C2—C1—C6—N2	−177.3 (2)	C12—C11—C13—C14	−2.9 (4)
C12—C7—C8—O5	−179.1 (2)	C10—C11—C13—C14	173.5 (2)
C12—C7—C8—C9	0.3 (3)	C3—C4—N1—O1	−1.4 (3)
O5—C8—C9—C10	178.5 (2)	C5—C4—N1—O1	176.1 (2)
C7—C8—C9—C10	−0.8 (3)	C3—C4—N1—O2	−180.0 (2)
C8—C9—C10—O6	−178.1 (2)	C5—C4—N1—O2	−2.5 (3)
C8—C9—C10—C11	0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O6i	0.93 (3)	2.28 (3)	3.067 (2)	141.5 (19)
N2—H2B···O6ii	0.93 (3)	2.36 (3)	3.241 (3)	157 (2)
O3—H3A···N1iii	0.84 (3)	2.59 (3)	3.358 (3)	153 (3)
O3—H3A···O1iii	0.84 (3)	2.39 (3)	2.953 (3)	125 (3)
O3—H3A···O2iii	0.84 (3)	2.13 (3)	2.975 (3)	178 (3)
O4—H4···N2	0.86 (3)	1.94 (3)	2.784 (2)	166 (2)
O5—H5A···O7i	0.88 (3)	1.87 (3)	2.748 (2)	175 (3)
O6—H6···O7	0.92 (3)	1.64 (3)	2.478 (2)	150 (2)
N1—O2···Cg2iv	1.22 (1)	3.82 (1)	3.599 (3)	70 (1)
C13—O7···Cg1v	1.25 (1)	3.52 (1)	3.722 (3)	89 (1)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C7–C12 and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O6i	0.93 (3)	2.28 (3)	3.067 (2)	141.5 (19)
N2—H2B⋯O6ii	0.93 (3)	2.36 (3)	3.241 (3)	157 (2)
O3—H3A⋯N1iii	0.84 (3)	2.59 (3)	3.358 (3)	153 (3)
O3—H3A⋯O1iii	0.84 (3)	2.39 (3)	2.953 (3)	125 (3)
O3—H3A⋯O2iii	0.84 (3)	2.13 (3)	2.975 (3)	178 (3)
O4—H4⋯N2	0.86 (3)	1.94 (3)	2.784 (2)	166 (2)
O5—H5A⋯O7i	0.88 (3)	1.87 (3)	2.748 (2)	175 (3)
O6—H6⋯O7	0.92 (3)	1.64 (3)	2.478 (2)	150 (2)
N1—O2⋯Cg2iv	1.22 (1)	3.82 (1)	3.599 (3)	70 (1)
C13—O7⋯Cg1v	1.25 (1)	3.52 (1)	3.722 (3)	89 (1)

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