Cystal structre of 5-hy-droxy-2-nitro-benzaldehyde.

In the title compound, C7H5NO4, the nitro group and the aldehyde group are inclined to the benzene ring by 16.6 (3) and 15.6 (3)°, respectively. In the crystal, mol-ecules are linked via O-H⋯O hydrogen bonds, forming chains along [100]. The chains are linked by C-H⋯O hydrogen bonds, forming a three-dimensional structure.

Related literature

For literature on nitro-substituted aromatic compounds and their various properties, see: Yan et al. (2006 ▸); Soojhawon et al. (2005 ▸). For crystal structures of related compounds, see: Tang et al. (2010 ▸); Tanak et al. (2009 ▸); Singh et al. (2009 ▸).

Experimental

Crystal data

C7H5NO4

M = 167.12

Monoclinic,

a = 9.6648 (18) Å

b = 5.0917 (10) Å

c = 14.920 (3) Å

β = 106.159 (4)°

V = 705.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 273 K

0.48 × 0.32 × 0.15 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▸) T min = 0.939, T max = 0.980

3884 measured reflections

1312 independent reflections

974 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.116

S = 1.04

1312 reflections

113 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2000 ▸); cell refinement: SAINT (Bruker, 2000 ▸); 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 ▸) and Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▸) and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S205698901500701X/su5113sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901500701X/su5113Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S205698901500701X/su5113Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S205698901500701X/su5113fig1.tif

The mol­ecular structure of title compound, with atom labelling. Displacement ellipsoids are drawn at 30% probability level.

Click here for additional data file.

b . DOI: 10.1107/S205698901500701X/su5113fig2.tif

The crystal packing of title compound, viewed along the b axis. Hydrogen bonds are shown as dashed lines (see Table 1 for details).

CCDC reference: 1058381

Additional supporting information: crystallographic information; 3D view; checkCIF report

C7H5NO4	F(000) = 344
Mr = 167.12	Dx = 1.574 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybc	Cell parameters from 924 reflections
a = 9.6648 (18) Å	θ = 2.8–23.7°
b = 5.0917 (10) Å	µ = 0.13 mm−1
c = 14.920 (3) Å	T = 273 K
β = 106.159 (4)°	Block, colourles
V = 705.2 (2) Å3	0.48 × 0.32 × 0.15 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	1312 independent reflections
Radiation source: fine-focus sealed tube	974 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω scan	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→11
Tmin = 0.939, Tmax = 0.980	k = −5→6
3884 measured reflections	l = −18→16

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) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0518P)2 + 0.1669P] where P = (Fo2 + 2Fc2)/3
1312 reflections	(Δ/σ)max < 0.001
113 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.16 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
O1	0.0034 (2)	0.9749 (4)	−0.12613 (15)	0.0961 (7)
O2	0.1401 (2)	0.9319 (3)	−0.21588 (12)	0.0763 (6)
O3	0.42366 (18)	0.1329 (3)	0.09957 (10)	0.0571 (5)
O4	0.39446 (19)	0.3765 (4)	−0.22575 (10)	0.0671 (5)
N1	0.1039 (2)	0.8710 (4)	−0.14662 (14)	0.0577 (5)
C1	0.1847 (2)	0.6689 (4)	−0.08470 (13)	0.0440 (5)
C2	0.1690 (2)	0.6549 (4)	0.00439 (15)	0.0524 (6)
H2A	0.1050	0.7672	0.0218	0.063*
C3	0.2468 (2)	0.4774 (4)	0.06721 (14)	0.0504 (6)
H3A	0.2356	0.4691	0.1271	0.061*
C4	0.3419 (2)	0.3104 (4)	0.04173 (12)	0.0421 (5)
C5	0.3562 (2)	0.3232 (4)	−0.04816 (12)	0.0420 (5)
H5A	0.4192	0.2086	−0.0654	0.050*
C6	0.2793 (2)	0.5012 (4)	−0.11264 (12)	0.0408 (5)
C7	0.2988 (3)	0.4856 (4)	−0.20759 (14)	0.0543 (6)
H7A	0.2307	0.5677	−0.2560	0.065*
H3B	0.411 (3)	0.140 (5)	0.156 (2)	0.078 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0934 (14)	0.1045 (16)	0.0934 (14)	0.0513 (13)	0.0311 (12)	0.0152 (12)
O2	0.1128 (15)	0.0612 (11)	0.0566 (10)	0.0066 (10)	0.0265 (10)	0.0107 (8)
O3	0.0801 (11)	0.0627 (10)	0.0343 (8)	0.0137 (8)	0.0256 (8)	0.0081 (7)
O4	0.0813 (11)	0.0887 (13)	0.0398 (8)	0.0127 (10)	0.0307 (8)	−0.0016 (8)
N1	0.0660 (13)	0.0515 (12)	0.0528 (11)	0.0033 (10)	0.0117 (10)	−0.0038 (9)
C1	0.0457 (11)	0.0436 (11)	0.0427 (11)	−0.0009 (9)	0.0123 (9)	−0.0025 (9)
C2	0.0578 (13)	0.0528 (13)	0.0542 (13)	0.0027 (11)	0.0280 (11)	−0.0087 (10)
C3	0.0650 (14)	0.0565 (13)	0.0377 (11)	−0.0020 (11)	0.0273 (11)	−0.0030 (10)
C4	0.0518 (12)	0.0423 (11)	0.0354 (10)	−0.0046 (9)	0.0175 (9)	−0.0022 (9)
C5	0.0479 (11)	0.0477 (12)	0.0342 (10)	−0.0005 (9)	0.0177 (9)	−0.0063 (9)
C6	0.0439 (11)	0.0466 (11)	0.0333 (10)	−0.0081 (9)	0.0129 (9)	−0.0064 (8)
C7	0.0685 (15)	0.0608 (14)	0.0337 (11)	0.0090 (12)	0.0144 (11)	0.0026 (10)

O1—N1	1.218 (2)	C2—H2A	0.9300
O2—N1	1.219 (3)	C3—C4	1.381 (3)
O3—C4	1.344 (2)	C3—H3A	0.9300
O3—H3B	0.88 (3)	C4—C5	1.387 (3)
O4—C7	1.173 (2)	C5—C6	1.379 (3)
N1—C1	1.457 (3)	C5—H5A	0.9300
C1—C2	1.381 (3)	C6—C7	1.482 (3)
C1—C6	1.397 (3)	C7—H7A	0.9300
C2—C3	1.367 (3)
C4—O3—H3B	111.7 (17)	O3—C4—C3	123.70 (17)
O1—N1—O2	122.6 (2)	O3—C4—C5	116.94 (18)
O1—N1—C1	118.2 (2)	C3—C4—C5	119.36 (18)
O2—N1—C1	119.2 (2)	C6—C5—C4	121.73 (18)
C2—C1—C6	120.82 (19)	C6—C5—H5A	119.1
C2—C1—N1	117.63 (19)	C4—C5—H5A	119.1
C6—C1—N1	121.50 (18)	C5—C6—C1	117.64 (17)
C3—C2—C1	120.47 (19)	C5—C6—C7	116.39 (18)
C3—C2—H2A	119.8	C1—C6—C7	125.87 (19)
C1—C2—H2A	119.8	O4—C7—C6	124.3 (2)
C2—C3—C4	119.97 (18)	O4—C7—H7A	117.8
C2—C3—H3A	120.0	C6—C7—H7A	117.8
C4—C3—H3A	120.0
O1—N1—C1—C2	−16.9 (3)	C3—C4—C5—C6	1.0 (3)
O2—N1—C1—C2	162.27 (19)	C4—C5—C6—C1	−0.5 (3)
O1—N1—C1—C6	165.7 (2)	C4—C5—C6—C7	−176.99 (18)
O2—N1—C1—C6	−15.2 (3)	C2—C1—C6—C5	−0.2 (3)
C6—C1—C2—C3	0.4 (3)	N1—C1—C6—C5	177.18 (18)
N1—C1—C2—C3	−177.03 (19)	C2—C1—C6—C7	175.9 (2)
C1—C2—C3—C4	0.0 (3)	N1—C1—C6—C7	−6.7 (3)
C2—C3—C4—O3	179.1 (2)	C5—C6—C7—O4	−17.1 (3)
C2—C3—C4—C5	−0.7 (3)	C1—C6—C7—O4	166.8 (2)
O3—C4—C5—C6	−178.86 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···O4i	0.88 (3)	1.82 (3)	2.699 (2)	174 (3)
C2—H2A···O1ii	0.93	2.48	3.364 (3)	158
C5—H5A···O3iii	0.93	2.45	3.379 (3)	173
C7—H7A···O1iv	0.93	2.49	3.264 (3)	140

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O3H3BO4i	0.88(3)	1.82(3)	2.699(2)	174(3)
C2H2AO1ii	0.93	2.48	3.364(3)	158
C5H5AO3iii	0.93	2.45	3.379(3)	173
C7H7AO1iv	0.93	2.49	3.264(3)	140

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