2-Hydr-oxy-5-nitro-benzaldehyde.

The title compound, C(7)H(5)NO(4), is essentially planar, with a maximum deviation from the mean plane of 0.0116 (11) Å for the hydr-oxy O atom. The mol-ecular and crystal structure are stabilized by intra- and inter-molecular inter-actions. An intra-molecular O-H⋯O hydrogen bond generates a six-membered ring, producing an S(6) ring motif. The C-H⋯O inter-actions result in the formation of C(5) chains and R(2) (2)(8) rings forming an approximately planar network parallel to (10). These planes are inter-connected through π-π inter-actions [centroid-centroid distance 3.582 (2) Å].

Related literature

Nitro­aromatics are widely used as inter­mediates in explosives, dyestuffs, pesticides and organic synthesis, see: Yan et al. (2006 ▶). They occur in industrial wastes and as direct pollutants in the environment and are relatively soluble in water and detecta­ble in rivers, ponds and soil, see: Yan et al. (2006 ▶); Soojhawon et al. (2005 ▶). Aromatic compounds with multiple nitro substituents are known to be resistant to electrophilic attack by oxygenases, see: Halas et al. (1983 ▶). For comparison bond lengths and angles in related structures, see: Rizal et al. (2008 ▶); Garden et al. (2004 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C7H5NO4

M = 167.12

Monoclinic,

a = 7.2580 (17) Å

b = 8.3960 (13) Å

c = 11.704 (3) Å

β = 95.165 (18)°

V = 710.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 296 K

0.54 × 0.28 × 0.15 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.979, T max = 0.992

4345 measured reflections

1396 independent reflections

944 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.119

S = 1.06

1396 reflections

112 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.15 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 PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046807/dn2510sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046807/dn2510Isup2.hkl

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

C7H5NO4	F(000) = 344
Mr = 167.12	Dx = 1.563 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8368 reflections
a = 7.2580 (17) Å	θ = 1.8–27.3°
b = 8.3960 (13) Å	µ = 0.13 mm−1
c = 11.704 (3) Å	T = 296 K
β = 95.165 (18)°	Prism., red
V = 710.3 (3) Å3	0.54 × 0.28 × 0.15 mm
Z = 4

Stoe IPDS II diffractometer	1396 independent reflections
Radiation source: fine-focus sealed tube	944 reflections with I > 2σ(I)
graphite	Rint = 0.062
Detector resolution: 6.67 pixels mm-1	θmax = 26.0°, θmin = 3.0°
rotation method scans	h = −8→8
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −10→10
Tmin = 0.979, Tmax = 0.992	l = −14→14
4345 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.05P)2 + 0.0581P] where P = (Fo2 + 2Fc2)/3
1396 reflections	(Δ/σ)max < 0.001
112 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

Experimental. 168 frames, detector distance = 120 mm

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O1	0.4340 (3)	−0.1006 (2)	0.25586 (14)	0.0788 (6)
O2	0.3658 (3)	−0.3022 (2)	0.15003 (16)	0.0819 (6)
O3	0.1019 (3)	0.2346 (2)	−0.19209 (14)	0.0702 (6)
H3A	0.130 (4)	0.336 (4)	−0.162 (3)	0.105*
O4	0.2251 (3)	0.4736 (2)	−0.06415 (16)	0.0895 (7)
N1	0.3709 (3)	−0.1591 (2)	0.16564 (16)	0.0524 (5)
C1	0.3019 (3)	−0.0545 (2)	0.07198 (17)	0.0425 (5)
C2	0.2232 (3)	−0.1209 (2)	−0.03011 (17)	0.0459 (5)
H2	0.2154	−0.2309	−0.0385	0.055*
C3	0.1574 (3)	−0.0228 (3)	−0.11799 (18)	0.0494 (5)
H3	0.1037	−0.0659	−0.1863	0.059*
C4	0.1711 (3)	0.1417 (2)	−0.10464 (18)	0.0471 (5)
C5	0.2551 (3)	0.2073 (2)	−0.00295 (17)	0.0437 (5)
C6	0.3190 (3)	0.1067 (2)	0.08585 (17)	0.0431 (5)
H6	0.3730	0.1485	0.1544	0.052*
C7	0.2771 (3)	0.3784 (3)	0.0104 (2)	0.0631 (7)
H7	0.3338	0.4172	0.0792	0.076*

	U11	U22	U33	U12	U13	U23
O1	0.1123 (15)	0.0673 (12)	0.0522 (10)	−0.0024 (11)	−0.0171 (10)	0.0069 (9)
O2	0.1202 (16)	0.0391 (10)	0.0829 (13)	0.0026 (9)	−0.0101 (11)	0.0101 (8)
O3	0.0914 (13)	0.0556 (11)	0.0590 (11)	0.0048 (9)	−0.0195 (9)	0.0061 (8)
O4	0.1338 (17)	0.0423 (10)	0.0871 (14)	0.0022 (11)	−0.0199 (12)	0.0094 (9)
N1	0.0593 (11)	0.0433 (12)	0.0547 (11)	−0.0005 (9)	0.0047 (9)	0.0071 (9)
C1	0.0418 (11)	0.0382 (12)	0.0475 (12)	−0.0002 (9)	0.0041 (9)	0.0023 (9)
C2	0.0486 (12)	0.0355 (10)	0.0535 (12)	−0.0007 (9)	0.0046 (9)	−0.0025 (9)
C3	0.0526 (12)	0.0492 (13)	0.0453 (12)	−0.0032 (10)	−0.0013 (9)	−0.0086 (10)
C4	0.0463 (11)	0.0458 (13)	0.0480 (12)	0.0029 (9)	−0.0018 (9)	0.0028 (10)
C5	0.0468 (11)	0.0366 (11)	0.0470 (12)	−0.0014 (9)	0.0007 (9)	−0.0008 (9)
C6	0.0457 (11)	0.0418 (12)	0.0413 (11)	−0.0031 (9)	0.0009 (9)	−0.0049 (9)
C7	0.0805 (17)	0.0424 (13)	0.0643 (15)	−0.0020 (12)	−0.0045 (12)	−0.0008 (12)

O1—N1	1.216 (2)	C2—H2	0.9300
O2—N1	1.215 (2)	C3—C4	1.392 (3)
O3—C4	1.348 (2)	C3—H3	0.9300
O3—H3A	0.93 (3)	C4—C5	1.401 (3)
O4—C7	1.218 (3)	C5—C6	1.386 (3)
N1—C1	1.458 (3)	C5—C7	1.452 (3)
C1—C6	1.367 (3)	C6—H6	0.9300
C1—C2	1.394 (3)	C7—H7	0.9300
C2—C3	1.370 (3)
C4—O3—H3A	100.5 (19)	O3—C4—C3	118.12 (19)
O2—N1—O1	122.27 (19)	O3—C4—C5	121.43 (19)
O2—N1—C1	118.59 (19)	C3—C4—C5	120.45 (19)
O1—N1—C1	119.13 (18)	C6—C5—C4	119.19 (18)
C6—C1—C2	121.56 (19)	C6—C5—C7	119.77 (19)
C6—C1—N1	119.05 (18)	C4—C5—C7	121.04 (19)
C2—C1—N1	119.38 (18)	C1—C6—C5	119.59 (19)
C3—C2—C1	119.5 (2)	C1—C6—H6	120.2
C3—C2—H2	120.3	C5—C6—H6	120.2
C1—C2—H2	120.3	O4—C7—C5	123.3 (2)
C2—C3—C4	119.71 (19)	O4—C7—H7	118.4
C2—C3—H3	120.1	C5—C7—H7	118.4
C4—C3—H3	120.1

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4i	0.93	2.50	3.427 (3)	175
C6—H6···O3ii	0.93	2.53	3.433 (3)	163
C7—H7···O2iii	0.93	2.50	3.176 (3)	130
O3—H3A···O4	0.93 (3)	1.73 (3)	2.613 (3)	157 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O4i	0.93	2.50	3.427 (3)	175
C6—H6⋯O3ii	0.93	2.53	3.433 (3)	163
C7—H7⋯O2iii	0.93	2.50	3.176 (3)	130
O3—H3A⋯O4	0.93 (3)	1.73 (3)	2.613 (3)	157 (3)

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