3-Hydr-oxy-4-nitro-phenyl acetate.

In the mol-ecule of the title compound, C(8)H(7)NO(5), the acetate group is oriented with respect to the aromatic ring at a dihedral angle of 85.30 (3)°. An intra-molecular O-H⋯O hydrogen bond results in the formation of a non-planar six-membered ring, adopting an envelope conformation. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules.

Related literature

For general background to phenolic esters as inter­mediates in organic synthesis, see: Trollsås et al. (1996 ▶); Svensson et al. (1998 ▶); Atkinson et al. (2005 ▶); Hu et al. (2001 ▶). For a related structure, see: Ji et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H7NO5

M = 197.15

Monoclinic,

a = 10.881 (2) Å

b = 5.0543 (10) Å

c = 15.318 (3) Å

β = 93.75 (3)°

V = 840.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 153 (2) K

0.24 × 0.20 × 0.16 mm

Data collection

Bruker SMART diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.969, T max = 0.979

5058 measured reflections

1449 independent reflections

1232 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.083

S = 1.12

1449 reflections

129 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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 PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808040981/hk2582sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040981/hk2582Isup2.hkl

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

C8H7NO5	F(000) = 408
Mr = 197.15	Dx = 1.558 Mg m−3
Monoclinic, P21/n	Melting point: 360 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.881 (2) Å	Cell parameters from 2650 reflections
b = 5.0543 (10) Å	θ = 2.2–27.5°
c = 15.318 (3) Å	µ = 0.13 mm−1
β = 93.75 (3)°	T = 153 K
V = 840.6 (3) Å3	Block, colorless
Z = 4	0.24 × 0.20 × 0.16 mm

Bruker P4 diffractometer	1449 independent reflections
Radiation source: fine-focus sealed tube	1232 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.969, Tmax = 0.979	k = −6→5
5058 measured reflections	l = −18→15

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0475P)2 + 0.1223P] where P = (Fo2 + 2Fc2)/3
1449 reflections	(Δ/σ)max = 0.001
129 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.20 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	0.14195 (8)	0.58036 (19)	0.89666 (6)	0.0279 (3)
O2	0.31702 (7)	0.35401 (18)	0.93249 (5)	0.0244 (3)
O3	0.59843 (8)	1.04495 (18)	0.88687 (5)	0.0223 (2)
H3	0.6350	1.1192	0.8486	0.033*
O4	0.67226 (8)	1.08418 (17)	0.72904 (5)	0.0230 (2)
O5	0.63078 (8)	0.77288 (18)	0.63478 (5)	0.0247 (2)
N1	0.61633 (9)	0.8778 (2)	0.70551 (6)	0.0179 (3)
C1	0.13908 (11)	0.2225 (3)	1.00085 (8)	0.0213 (3)
H1A	0.0532	0.2620	1.0041	0.032*
H1B	0.1807	0.2425	1.0577	0.032*
H1C	0.1482	0.0438	0.9810	0.032*
C2	0.19373 (11)	0.4079 (2)	0.93821 (7)	0.0179 (3)
C3	0.38267 (10)	0.5030 (3)	0.87381 (8)	0.0195 (3)
C4	0.38272 (11)	0.4184 (3)	0.78716 (8)	0.0207 (3)
H4	0.3323	0.2804	0.7666	0.025*
C5	0.46001 (11)	0.5463 (2)	0.73292 (8)	0.0194 (3)
H5	0.4633	0.4919	0.6751	0.023*
C6	0.53337 (10)	0.7573 (2)	0.76450 (7)	0.0164 (3)
C7	0.53043 (10)	0.8455 (2)	0.85126 (7)	0.0168 (3)
C8	0.45238 (10)	0.7116 (2)	0.90598 (7)	0.0189 (3)
H8	0.4480	0.7643	0.9639	0.023*

	U11	U22	U33	U12	U13	U23
O1	0.0222 (5)	0.0277 (6)	0.0342 (5)	0.0061 (4)	0.0054 (4)	0.0129 (4)
O2	0.0180 (5)	0.0266 (5)	0.0290 (5)	0.0010 (4)	0.0041 (3)	0.0131 (4)
O3	0.0269 (5)	0.0225 (5)	0.0177 (4)	−0.0062 (4)	0.0019 (4)	−0.0023 (3)
O4	0.0233 (5)	0.0224 (5)	0.0232 (5)	−0.0057 (4)	0.0018 (3)	−0.0005 (4)
O5	0.0302 (5)	0.0282 (5)	0.0164 (4)	0.0030 (4)	0.0064 (4)	−0.0034 (4)
N1	0.0165 (5)	0.0200 (6)	0.0171 (5)	0.0032 (4)	0.0004 (4)	0.0005 (4)
C1	0.0219 (6)	0.0208 (7)	0.0216 (6)	−0.0008 (5)	0.0033 (5)	0.0030 (5)
C2	0.0176 (6)	0.0169 (6)	0.0190 (6)	−0.0003 (5)	0.0003 (5)	−0.0026 (5)
C3	0.0143 (6)	0.0208 (7)	0.0235 (6)	0.0042 (5)	0.0021 (5)	0.0071 (5)
C4	0.0177 (6)	0.0182 (7)	0.0255 (7)	−0.0008 (5)	−0.0033 (5)	0.0010 (5)
C5	0.0204 (6)	0.0191 (7)	0.0180 (6)	0.0029 (5)	−0.0022 (5)	−0.0012 (5)
C6	0.0150 (6)	0.0177 (6)	0.0166 (6)	0.0033 (5)	0.0012 (4)	0.0018 (4)
C7	0.0162 (6)	0.0158 (6)	0.0182 (6)	0.0035 (5)	−0.0016 (4)	−0.0003 (5)
C8	0.0197 (6)	0.0211 (7)	0.0159 (6)	0.0043 (5)	0.0022 (5)	0.0017 (5)

O1—C2	1.1982 (15)	C1—H1C	0.9600
O2—C2	1.3773 (15)	C3—C8	1.3716 (18)
O2—C3	1.4032 (14)	C3—C4	1.3944 (17)
O3—C7	1.3447 (15)	C4—C5	1.3807 (17)
O3—H3	0.8200	C4—H4	0.9300
O4—N1	1.2489 (13)	C5—C6	1.3994 (17)
O5—N1	1.2255 (12)	C5—H5	0.9300
N1—C6	1.4521 (15)	C6—C7	1.4041 (16)
C1—C2	1.4923 (16)	C7—C8	1.4054 (17)
C1—H1A	0.9600	C8—H8	0.9300
C1—H1B	0.9600
C2—O2—C3	118.26 (9)	C4—C3—O2	118.51 (11)
C7—O3—H3	109.5	C5—C4—C3	117.87 (12)
O5—N1—O4	121.88 (10)	C5—C4—H4	121.1
O5—N1—C6	119.32 (10)	C3—C4—H4	121.1
O4—N1—C6	118.79 (9)	C4—C5—C6	120.33 (11)
C2—C1—H1A	109.5	C4—C5—H5	119.8
C2—C1—H1B	109.5	C6—C5—H5	119.8
H1A—C1—H1B	109.5	C5—C6—C7	121.42 (11)
C2—C1—H1C	109.5	C5—C6—N1	117.92 (10)
H1A—C1—H1C	109.5	C7—C6—N1	120.63 (11)
H1B—C1—H1C	109.5	O3—C7—C6	125.16 (10)
O1—C2—O2	122.43 (11)	O3—C7—C8	117.20 (10)
O1—C2—C1	127.24 (11)	C6—C7—C8	117.62 (11)
O2—C2—C1	110.33 (10)	C3—C8—C7	119.85 (11)
C8—C3—C4	122.88 (11)	C3—C8—H8	120.1
C8—C3—O2	118.37 (10)	C7—C8—H8	120.1
C3—O2—C2—O1	−1.83 (17)	O5—N1—C6—C7	169.13 (10)
C3—O2—C2—C1	177.59 (10)	O4—N1—C6—C7	−9.92 (16)
C2—O2—C3—C8	98.78 (13)	C5—C6—C7—O3	179.46 (10)
C2—O2—C3—C4	−86.75 (14)	N1—C6—C7—O3	1.57 (18)
C8—C3—C4—C5	2.32 (18)	C5—C6—C7—C8	0.95 (17)
O2—C3—C4—C5	−171.88 (10)	N1—C6—C7—C8	−176.94 (10)
C3—C4—C5—C6	−1.34 (18)	C4—C3—C8—C7	−1.64 (18)
C4—C5—C6—C7	−0.25 (18)	O2—C3—C8—C7	172.57 (10)
C4—C5—C6—N1	177.70 (10)	O3—C7—C8—C3	−178.67 (10)
O5—N1—C6—C5	−8.83 (15)	C6—C7—C8—C3	−0.03 (17)
O4—N1—C6—C5	172.12 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.82	1.91	2.605 (2)	142
C5—H5···O1i	0.93	2.58	3.229 (2)	127
C8—H8···O3ii	0.93	2.56	3.481 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4	0.82	1.91	2.605 (2)	142
C5—H5⋯O1i	0.93	2.58	3.229 (2)	127
C8—H8⋯O3ii	0.93	2.56	3.481 (2)	170

Symmetry codes: (i) ; (ii) .