2-Hy-droxy-3-nitro-benzaldehyde.

The title compound, C(7)H(5)NO(4), isolated from the leaves of Actephila merrilliana, is essentially planar (r.m.s. deviation = 0.026 Å). The conformation is supported by an intra-molecular O-H⋯O hydrogen bond, which generates an S(6) ring. In the crystal, C-H⋯O inter-actions and aromatic π-π stacking [centroid-centroid distance = 3.754 (4) Å] help to establish the packing.

Related literature

For medicinal background, see: Ovenden et al. (2001 ▶); Song et al. (2007 ▶). For related structures, see: Rizal et al. (2008 ▶); Garden et al. (2004 ▶).

Experimental

Crystal data

C7H5NO4

M = 167.12

Monoclinic,

a = 8.8276 (7) Å

b = 8.7296 (8) Å

c = 9.011 (9) Å

β = 90.124 (1)°

V = 694.4 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 298 K

0.48 × 0.48 × 0.42 mm

Data collection

Bruker SMART CCD diffractometer

3289 measured reflections

1230 independent reflections

929 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.119

S = 1.07

1230 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); 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/S1600536810025110/hb5495sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025110/hb5495Isup2.hkl

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

C7H5NO4	F(000) = 344
Mr = 167.12	Dx = 1.599 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1493 reflections
a = 8.8276 (7) Å	θ = 2.3–27.7°
b = 8.7296 (8) Å	µ = 0.13 mm−1
c = 9.011 (9) Å	T = 298 K
β = 90.124 (1)°	Block, colourless
V = 694.4 (7) Å3	0.48 × 0.48 × 0.42 mm
Z = 4

Bruker SMART CCD diffractometer	929 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
graphite	θmax = 25.0°, θmin = 3.2°
phi and ω scans	h = −6→10
3289 measured reflections	k = −9→10
1230 independent reflections	l = −10→10

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0617P)2 + 0.1126P] where P = (Fo2 + 2Fc2)/3
1230 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.17 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
N1	0.50055 (17)	0.84855 (17)	0.75856 (18)	0.0503 (5)
O1	0.29576 (16)	0.32129 (17)	0.56300 (17)	0.0660 (5)
O2	0.33112 (14)	0.61257 (16)	0.61024 (14)	0.0548 (4)
H2	0.2948	0.5346	0.5739	0.082*
O3	0.4312 (2)	0.89120 (17)	0.6494 (2)	0.0793 (5)
O4	0.55192 (19)	0.93655 (17)	0.85100 (18)	0.0769 (5)
C1	0.3983 (2)	0.2987 (2)	0.6511 (2)	0.0519 (5)
H1	0.4261	0.1978	0.6698	0.062*
C2	0.48004 (18)	0.4189 (2)	0.72888 (18)	0.0391 (4)
C3	0.44390 (18)	0.5747 (2)	0.70290 (18)	0.0376 (4)
C4	0.52863 (19)	0.68465 (19)	0.77951 (19)	0.0390 (4)
C5	0.64236 (19)	0.6430 (2)	0.8776 (2)	0.0440 (5)
H5	0.6965	0.7184	0.9277	0.053*
C6	0.67596 (19)	0.4909 (2)	0.9015 (2)	0.0490 (5)
H6	0.7529	0.4634	0.9669	0.059*
C7	0.5946 (2)	0.3804 (2)	0.8277 (2)	0.0451 (5)
H7	0.6168	0.2776	0.8444	0.054*

	U11	U22	U33	U12	U13	U23
N1	0.0559 (10)	0.0375 (9)	0.0574 (11)	−0.0026 (7)	−0.0013 (8)	−0.0013 (8)
O1	0.0698 (10)	0.0569 (9)	0.0712 (10)	−0.0092 (7)	−0.0219 (8)	−0.0111 (7)
O2	0.0597 (8)	0.0466 (8)	0.0580 (8)	0.0000 (6)	−0.0271 (7)	0.0031 (6)
O3	0.1053 (13)	0.0440 (9)	0.0886 (12)	0.0024 (8)	−0.0348 (10)	0.0140 (8)
O4	0.1027 (13)	0.0452 (9)	0.0828 (11)	−0.0027 (8)	−0.0148 (9)	−0.0167 (8)
C1	0.0595 (12)	0.0415 (10)	0.0546 (12)	−0.0029 (9)	−0.0042 (10)	−0.0039 (9)
C2	0.0439 (10)	0.0373 (10)	0.0362 (9)	0.0015 (7)	0.0008 (7)	0.0003 (7)
C3	0.0403 (9)	0.0396 (9)	0.0329 (9)	0.0007 (7)	−0.0037 (7)	0.0014 (7)
C4	0.0433 (9)	0.0344 (9)	0.0392 (9)	−0.0012 (7)	−0.0007 (7)	0.0004 (7)
C5	0.0413 (10)	0.0477 (11)	0.0429 (10)	−0.0058 (8)	−0.0039 (8)	−0.0032 (8)
C6	0.0440 (10)	0.0569 (12)	0.0461 (11)	0.0047 (8)	−0.0091 (8)	0.0014 (9)
C7	0.0486 (10)	0.0429 (10)	0.0438 (10)	0.0094 (8)	−0.0007 (8)	0.0036 (8)

N1—O3	1.216 (2)	C2—C3	1.416 (2)
N1—O4	1.220 (2)	C3—C4	1.399 (3)
N1—C4	1.464 (2)	C4—C5	1.384 (2)
O1—C1	1.219 (2)	C5—C6	1.377 (3)
O2—C3	1.340 (2)	C5—H5	0.9300
O2—H2	0.8200	C6—C7	1.374 (3)
C1—C2	1.452 (3)	C6—H6	0.9300
C1—H1	0.9300	C7—H7	0.9300
C2—C7	1.388 (2)
O3—N1—O4	123.06 (18)	C5—C4—C3	121.42 (17)
O3—N1—C4	119.23 (15)	C5—C4—N1	117.45 (15)
O4—N1—C4	117.69 (17)	C3—C4—N1	121.13 (16)
C3—O2—H2	109.5	C6—C5—C4	120.55 (16)
O1—C1—C2	124.42 (19)	C6—C5—H5	119.7
O1—C1—H1	117.8	C4—C5—H5	119.7
C2—C1—H1	117.8	C7—C6—C5	119.31 (17)
C7—C2—C3	120.15 (16)	C7—C6—H6	120.3
C7—C2—C1	119.71 (18)	C5—C6—H6	120.3
C3—C2—C1	120.14 (17)	C6—C7—C2	121.32 (18)
O2—C3—C4	122.28 (16)	C6—C7—H7	119.3
O2—C3—C2	120.47 (16)	C2—C7—H7	119.3
C4—C3—C2	117.24 (16)
O1—C1—C2—C7	179.64 (18)	O3—N1—C4—C5	161.56 (17)
O1—C1—C2—C3	−0.9 (3)	O4—N1—C4—C5	−16.7 (2)
C7—C2—C3—O2	−178.44 (15)	O3—N1—C4—C3	−18.3 (3)
C1—C2—C3—O2	2.1 (2)	O4—N1—C4—C3	163.53 (16)
C7—C2—C3—C4	0.5 (2)	C3—C4—C5—C6	0.5 (3)
C1—C2—C3—C4	−178.95 (15)	N1—C4—C5—C6	−179.32 (16)
O2—C3—C4—C5	178.41 (15)	C4—C5—C6—C7	−0.5 (3)
C2—C3—C4—C5	−0.5 (2)	C5—C6—C7—C2	0.5 (3)
O2—C3—C4—N1	−1.8 (3)	C3—C2—C7—C6	−0.5 (3)
C2—C3—C4—N1	179.32 (14)	C1—C2—C7—C6	178.94 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	1.86	2.597 (3)	148
C5—H5···O2i	0.93	2.51	3.422 (4)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.82	1.86	2.597 (3)	148
C5—H5⋯O2i	0.93	2.51	3.422 (4)	168

Symmetry code: (i) .