4-Hydr-oxy-3-nitro-benzaldehyde.

The hydroxyl group in each of the two independent mol-ecules of the title compound, C(7)H(5)NO(4), participates in two O-H⋯O hydrogen bonds, viz. one intra-molecular bond to the nitro group and one inter-molecular bond to the aldehyde group of the same mol-ecule in the next unit, resulting in a linear chain structure. The dihedral angle between the aromatic ring and the nitro group is 10.9 (3)° in one mol-ecule and 9.9 (2)° in the other.

Related literature

For the structure of 2-nitro­phenol, see: Iwasaki & Kawano (1978 ▶). For the structure of 4-hydroxy­benzaldehyde, see: Jasinski et al. (2008 ▶).

Experimental

Crystal data

C7H5NO4

M = 167.12

Triclinic,

a = 8.042 (1) Å

b = 8.036 (1) Å

c = 12.242 (2) Å

α = 71.975 (2)°

β = 70.820 (2)°

γ = 67.323 (2)°

V = 674.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 100 (2) K

0.40 × 0.05 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: none

4245 measured reflections

3068 independent reflections

2134 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.121

S = 0.99

3068 reflections

225 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011148/fl2191sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011148/fl2191Isup2.hkl

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

C7H5NO4	Z = 4
Mr = 167.12	F000 = 344
Triclinic, P1	Dx = 1.647 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.042 (1) Å	Cell parameters from 1123 reflections
b = 8.036 (1) Å	θ = 3.0–28.8º
c = 12.242 (2) Å	µ = 0.14 mm−1
α = 71.975 (2)º	T = 100 (2) K
β = 70.820 (2)º	Prism, yellow
γ = 67.323 (2)º	0.40 × 0.05 × 0.05 mm
V = 674.1 (2) Å3

Bruker SMART APEXII diffractometer	2134 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
Monochromator: graphite	θmax = 27.5º
T = 100(2) K	θmin = 1.8º
φ and ω scans	h = −10→10
Absorption correction: none	k = −10→9
4245 measured reflections	l = −15→15
3068 independent reflections

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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121	w = 1/[σ2(Fo2) + (0.0598P)2 + 0.2315P] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
3068 reflections	Δρmax = 0.31 e Å−3
225 parameters	Δρmin = −0.32 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
O1	0.4321 (2)	0.8384 (2)	0.8786 (1)	0.0221 (3)
O2	0.9772 (2)	0.2412 (2)	1.1704 (1)	0.0225 (4)
O3	1.1859 (2)	0.0816 (2)	1.0449 (1)	0.0224 (4)
O4	1.1227 (2)	0.1121 (2)	0.8402 (1)	0.0204 (3)
O5	1.0630 (2)	0.6755 (2)	0.4971 (1)	0.0220 (3)
O6	0.4719 (2)	1.2568 (2)	0.7806 (1)	0.0277 (4)
O7	0.2851 (2)	1.4257 (2)	0.6664 (1)	0.0231 (4)
O8	0.3813 (2)	1.4045 (2)	0.4424 (1)	0.0199 (3)
N1	1.0379 (2)	0.2049 (2)	1.0719 (2)	0.0173 (4)
N2	0.4272 (2)	1.2985 (2)	0.6866 (2)	0.0189 (4)
C1	0.5276 (3)	0.7418 (3)	0.9488 (2)	0.0175 (4)
C2	0.6821 (3)	0.5734 (3)	0.9247 (2)	0.0157 (4)
C3	0.7856 (3)	0.4675 (3)	1.0075 (2)	0.0160 (4)
C4	0.9342 (3)	0.3115 (3)	0.9816 (2)	0.0153 (4)
C5	0.9815 (3)	0.2577 (3)	0.8741 (2)	0.0162 (4)
C6	0.8705 (3)	0.3642 (3)	0.7931 (2)	0.0193 (4)
C7	0.7247 (3)	0.5181 (3)	0.8181 (2)	0.0185 (4)
C8	0.9568 (3)	0.7675 (3)	0.5691 (2)	0.0181 (4)
C9	0.8044 (3)	0.9364 (3)	0.5399 (2)	0.0157 (4)
C10	0.6886 (3)	1.0378 (3)	0.6244 (2)	0.0157 (4)
C11	0.5444 (3)	1.1966 (3)	0.5950 (2)	0.0157 (4)
C12	0.5144 (3)	1.2565 (3)	0.4804 (2)	0.0155 (4)
C13	0.6380 (3)	1.1535 (3)	0.3950 (2)	0.0174 (4)
C14	0.7784 (3)	0.9973 (3)	0.4242 (2)	0.0173 (4)
H4o	1.185 (4)	0.068 (4)	0.892 (2)	0.06 (1)*
H8o	0.308 (3)	1.452 (4)	0.499 (2)	0.05 (1)*
H1	0.5013	0.7765	1.0216	0.021*
H3	0.7557	0.5010	1.0812	0.019*
H6	0.8969	0.3290	0.7203	0.023*
H7	0.6514	0.5884	0.7623	0.022*
H8	0.9724	0.7290	0.6477	0.022*
H10	0.7070	0.9998	0.7023	0.019*
H13	0.6238	1.1931	0.3161	0.021*
H14	0.8593	0.9290	0.3655	0.021*

	U11	U22	U33	U12	U13	U23
O1	0.0187 (8)	0.0176 (8)	0.0236 (8)	0.0041 (6)	−0.0081 (6)	−0.0052 (6)
O2	0.0246 (8)	0.0218 (8)	0.0174 (7)	−0.0016 (7)	−0.0057 (6)	−0.0057 (6)
O3	0.0171 (8)	0.0177 (8)	0.0261 (8)	0.0048 (6)	−0.0082 (6)	−0.0059 (6)
O4	0.0169 (8)	0.0172 (8)	0.0234 (8)	0.0048 (6)	−0.0073 (6)	−0.0096 (6)
O5	0.0191 (8)	0.0171 (8)	0.0251 (8)	0.0038 (6)	−0.0071 (6)	−0.0083 (6)
O6	0.0294 (9)	0.0283 (9)	0.0199 (8)	0.0037 (7)	−0.0080 (7)	−0.0121 (7)
O7	0.0175 (8)	0.0186 (8)	0.0241 (8)	0.0047 (6)	−0.0035 (6)	−0.0075 (6)
O8	0.0155 (8)	0.0171 (7)	0.0197 (8)	0.0049 (6)	−0.0051 (6)	−0.0060 (6)
N1	0.0170 (9)	0.0152 (9)	0.0187 (9)	−0.0028 (7)	−0.0058 (7)	−0.0035 (7)
N2	0.0171 (9)	0.0166 (9)	0.0189 (9)	−0.0004 (7)	−0.0029 (7)	−0.0063 (7)
C1	0.0149 (10)	0.0145 (10)	0.0201 (10)	−0.0005 (8)	−0.0023 (8)	−0.0065 (8)
C2	0.0104 (9)	0.0135 (10)	0.0198 (10)	−0.0007 (8)	−0.0025 (8)	−0.0040 (8)
C3	0.0149 (10)	0.0149 (10)	0.0163 (10)	−0.0025 (8)	−0.0033 (8)	−0.0038 (8)
C4	0.0134 (10)	0.0138 (10)	0.0167 (10)	−0.0026 (8)	−0.0055 (8)	−0.0006 (8)
C5	0.0117 (10)	0.0142 (10)	0.0204 (10)	−0.0006 (8)	−0.0038 (8)	−0.0048 (8)
C6	0.0177 (11)	0.0187 (11)	0.0197 (10)	0.0010 (8)	−0.0060 (9)	−0.0085 (8)
C7	0.0149 (10)	0.0175 (10)	0.0202 (10)	−0.0001 (8)	−0.0070 (8)	−0.0034 (8)
C8	0.0167 (10)	0.0153 (10)	0.0199 (10)	−0.0018 (8)	−0.0057 (8)	−0.0034 (8)
C9	0.0145 (10)	0.0119 (10)	0.0195 (10)	−0.0020 (8)	−0.0054 (8)	−0.0031 (8)
C10	0.0154 (10)	0.0147 (10)	0.0155 (10)	−0.0034 (8)	−0.0047 (8)	−0.0017 (8)
C11	0.0132 (10)	0.0135 (10)	0.0182 (10)	−0.0018 (8)	−0.0021 (8)	−0.0053 (8)
C12	0.0123 (10)	0.0121 (9)	0.0196 (10)	−0.0013 (8)	−0.0040 (8)	−0.0032 (8)
C13	0.0153 (10)	0.0170 (10)	0.0171 (10)	0.0000 (8)	−0.0057 (8)	−0.0043 (8)
C14	0.0150 (10)	0.0152 (10)	0.0189 (10)	0.0006 (8)	−0.0033 (8)	−0.0075 (8)

O1—C1	1.222 (2)	C8—C9	1.475 (3)
O2—N1	1.223 (2)	C9—C10	1.380 (3)
O3—N1	1.242 (2)	C9—C14	1.406 (3)
O4—C5	1.341 (2)	C10—C11	1.397 (3)
O5—C8	1.214 (3)	C11—C12	1.405 (3)
O6—N2	1.226 (2)	C12—C13	1.408 (3)
O7—N2	1.241 (2)	C13—C14	1.368 (3)
O8—C12	1.335 (2)	O4—H4o	0.84 (1)
N1—C4	1.457 (3)	O8—H8o	0.84 (1)
N2—C11	1.447 (3)	C1—H1	0.9500
C1—C2	1.473 (3)	C3—H3	0.9500
C2—C3	1.385 (3)	C6—H6	0.9500
C2—C7	1.403 (3)	C7—H7	0.9500
C3—C4	1.394 (3)	C8—H8	0.9500
C4—C5	1.399 (3)	C10—H10	0.9500
C5—C6	1.408 (3)	C13—H13	0.9500
C6—C7	1.370 (3)	C14—H14	0.9500
O2—N1—O3	122.8 (2)	C10—C11—N2	117.7 (2)
O2—N1—C4	119.0 (2)	C12—C11—N2	121.0 (2)
O3—N1—C4	118.1 (2)	O8—C12—C11	126.7 (2)
O6—N2—O7	122.6 (2)	O8—C12—C13	115.7 (2)
O6—N2—C11	119.1 (2)	C11—C12—C13	117.7 (2)
O7—N2—C11	118.3 (2)	C14—C13—C12	120.9 (2)
O1—C1—C2	122.4 (2)	C13—C14—C9	120.9 (2)
C3—C2—C7	119.4 (2)	C5—O4—H4o	106 (2)
C3—C2—C1	120.4 (2)	C12—O8—H8o	110 (2)
C7—C2—C1	120.3 (2)	O1—C1—H1	118.8
C2—C3—C4	119.4 (2)	C2—C1—H1	118.8
C3—C4—C5	121.8 (2)	C2—C3—H3	120.3
C3—C4—N1	117.1 (2)	C4—C3—H3	120.3
C5—C4—N1	121.1 (2)	C7—C6—H6	119.7
O4—C5—C4	126.4 (2)	C5—C6—H6	119.7
O4—C5—C6	115.9 (2)	C6—C7—H7	119.5
C4—C5—C6	117.7 (2)	C2—C7—H7	119.5
C7—C6—C5	120.6 (2)	O5—C8—H8	118.5
C6—C7—C2	121.1 (2)	C9—C8—H8	118.5
O5—C8—C9	122.9 (2)	C9—C10—H10	120.1
C10—C9—C14	119.4 (2)	C11—C10—H10	120.1
C10—C9—C8	120.8 (2)	C14—C13—H13	119.5
C14—C9—C8	119.8 (2)	C12—C13—H13	119.5
C9—C10—C11	119.8 (2)	C13—C14—H14	119.6
C10—C11—C12	121.3 (2)	C9—C14—H14	119.6
O1—C1—C2—C3	−179.5 (2)	O5—C8—C9—C10	−179.1 (2)
O1—C1—C2—C7	0.0 (3)	O5—C8—C9—C14	−0.3 (3)
C7—C2—C3—C4	2.1 (3)	C14—C9—C10—C11	1.7 (3)
C1—C2—C3—C4	−178.3 (2)	C8—C9—C10—C11	−179.5 (2)
C2—C3—C4—C5	−0.4 (3)	C9—C10—C11—C12	−0.3 (3)
C2—C3—C4—N1	−179.8 (2)	C9—C10—C11—N2	−179.8 (2)
O2—N1—C4—C3	9.5 (3)	O6—N2—C11—C10	9.2 (3)
O3—N1—C4—C3	−169.8 (2)	O7—N2—C11—C10	−171.1 (2)
O2—N1—C4—C5	−170.0 (2)	O6—N2—C11—C12	−170.3 (2)
O3—N1—C4—C5	10.7 (3)	O7—N2—C11—C12	9.4 (3)
C3—C4—C5—O4	179.0 (2)	C10—C11—C12—O8	179.6 (2)
N1—C4—C5—O4	−1.6 (3)	N2—C11—C12—O8	−0.9 (3)
C3—C4—C5—C6	−1.6 (3)	C10—C11—C12—C13	−1.6 (3)
N1—C4—C5—C6	177.8 (2)	N2—C11—C12—C13	177.9 (2)
O4—C5—C6—C7	−178.7 (2)	O8—C12—C13—C14	−179.0 (2)
C4—C5—C6—C7	1.9 (3)	C11—C12—C13—C14	2.1 (3)
C5—C6—C7—C2	−0.1 (3)	C12—C13—C14—C9	−0.8 (3)
C3—C2—C7—C6	−2.0 (3)	C10—C9—C14—C13	−1.2 (3)
C1—C2—C7—C6	178.5 (2)	C8—C9—C14—C13	180.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4o···O1i	0.84 (1)	2.13 (3)	2.676 (2)	122 (3)
O4—H4o···O3	0.84 (1)	1.91 (2)	2.638 (2)	144 (3)
O8—H8o···O5ii	0.84 (1)	2.10 (3)	2.687 (2)	128 (3)
O8—H8o···O7	0.84 (1)	1.94 (2)	2.635 (2)	139 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4o⋯O1i	0.84 (1)	2.13 (3)	2.676 (2)	122 (3)
O4—H4o⋯O3	0.84 (1)	1.91 (2)	2.638 (2)	144 (3)
O8—H8o⋯O5ii	0.84 (1)	2.10 (3)	2.687 (2)	128 (3)
O8—H8o⋯O7	0.84 (1)	1.94 (2)	2.635 (2)	139 (3)

Symmetry codes: (i) ; (ii) .