4-Hydr-oxy-3-nitro-phenyl penta-noate.

In the title compound, C(11)H(13)NO(5), an intra-molecular O-H⋯O hydrogen bond is formed between the hydr-oxy and the nitro groups, which results in the formation of a six-membered ring. The valer-oxy group shows a torsioned conformation, and connects to the aryl ring with a C-C-O-C torsion angle of 102.34 (1)°.

Related literature

For general background to the use of 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 & Li (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H13NO5

M = 239.22

Triclinic,

a = 5.3006 (14) Å

b = 10.435 (2) Å

c = 11.365 (3) Å

α = 67.340 (12)°

β = 81.074 (17)°

γ = 77.114 (16)°

V = 563.8 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 113 K

0.18 × 0.06 × 0.06 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2007 ▶) T min = 0.980, T max = 0.993

5175 measured reflections

2639 independent reflections

1972 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.100

S = 1.00

2639 reflections

158 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810002795/bg2323sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002795/bg2323Isup2.hkl

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

C11H13NO5	Z = 2
Mr = 239.22	F(000) = 252
Triclinic, P1	Dx = 1.409 Mg m−3
Hall symbol: -P 1	Melting point: 310 K
a = 5.3006 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.435 (2) Å	Cell parameters from 1965 reflections
c = 11.365 (3) Å	θ = 2.1–27.9°
α = 67.340 (12)°	µ = 0.11 mm−1
β = 81.074 (17)°	T = 113 K
γ = 77.114 (16)°	Prism, colorless
V = 563.8 (2) Å3	0.18 × 0.06 × 0.06 mm

Rigaku Saturn CCD area-detector diffractometer	2639 independent reflections
Radiation source: fine-focus sealed tube	1972 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 2.2°
ω and φ scans	h = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2007)	k = −13→13
Tmin = 0.980, Tmax = 0.993	l = −14→14
5175 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0553P)2] where P = (Fo2 + 2Fc2)/3
2639 reflections	(Δ/σ)max = 0.001
158 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.27 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	0.44132 (16)	0.16466 (9)	1.06926 (8)	0.0260 (2)
O2	0.57276 (18)	0.35065 (8)	1.06023 (9)	0.0294 (2)
O3	0.97659 (17)	0.43498 (8)	0.91208 (9)	0.0266 (2)
H3	0.849 (3)	0.4414 (15)	0.9691 (14)	0.040*
O4	1.05538 (15)	−0.03140 (8)	0.78112 (8)	0.0208 (2)
O5	0.75270 (16)	0.06969 (8)	0.63771 (8)	0.0238 (2)
N1	0.59085 (19)	0.24914 (10)	1.02548 (9)	0.0206 (2)
C1	0.8163 (2)	0.11536 (11)	0.89438 (11)	0.0183 (3)
H1	0.6925	0.0544	0.9283	0.022*
C2	0.7982 (2)	0.23078 (11)	0.93060 (10)	0.0175 (3)
C3	0.9768 (2)	0.32268 (11)	0.88102 (11)	0.0194 (3)
C4	1.1752 (2)	0.29541 (12)	0.79260 (11)	0.0218 (3)
H4	1.2982	0.3567	0.7566	0.026*
C5	1.1953 (2)	0.18137 (12)	0.75690 (11)	0.0209 (3)
H5	1.3315	0.1641	0.6969	0.025*
C6	1.0158 (2)	0.09177 (11)	0.80900 (11)	0.0181 (3)
C7	0.9099 (2)	−0.03100 (12)	0.69151 (10)	0.0178 (3)
C8	0.9818 (2)	−0.16744 (12)	0.66970 (11)	0.0197 (3)
H8A	1.0362	−0.2441	0.7506	0.024*
H8B	1.1326	−0.1620	0.6056	0.024*
C9	0.7641 (2)	−0.20491 (11)	0.62381 (11)	0.0210 (3)
H9A	0.6992	−0.1255	0.5467	0.025*
H9B	0.6189	−0.2196	0.6911	0.025*
C10	0.8556 (2)	−0.33818 (12)	0.59220 (12)	0.0238 (3)
H10A	0.9660	−0.3154	0.5108	0.029*
H10B	0.9636	−0.4093	0.6601	0.029*
C11	0.6337 (3)	−0.40135 (13)	0.58021 (14)	0.0332 (3)
H11A	0.5280	−0.4282	0.6618	0.050*
H11B	0.7039	−0.4851	0.5581	0.050*
H11C	0.5260	−0.3316	0.5130	0.050*

	U11	U22	U33	U12	U13	U23
O1	0.0254 (5)	0.0286 (5)	0.0263 (5)	−0.0112 (4)	0.0048 (4)	−0.0114 (4)
O2	0.0387 (6)	0.0213 (4)	0.0310 (5)	−0.0050 (4)	0.0060 (4)	−0.0161 (4)
O3	0.0329 (5)	0.0241 (5)	0.0303 (5)	−0.0113 (4)	0.0036 (4)	−0.0170 (4)
O4	0.0237 (5)	0.0196 (4)	0.0229 (5)	0.0002 (3)	−0.0061 (3)	−0.0125 (3)
O5	0.0254 (5)	0.0229 (4)	0.0236 (5)	0.0022 (4)	−0.0063 (4)	−0.0108 (3)
N1	0.0229 (6)	0.0190 (5)	0.0191 (5)	−0.0016 (4)	−0.0013 (4)	−0.0076 (4)
C1	0.0187 (6)	0.0177 (5)	0.0192 (6)	−0.0047 (4)	−0.0034 (5)	−0.0058 (4)
C2	0.0185 (6)	0.0181 (5)	0.0154 (6)	−0.0012 (4)	−0.0015 (4)	−0.0066 (4)
C3	0.0239 (6)	0.0170 (5)	0.0187 (6)	−0.0027 (5)	−0.0049 (5)	−0.0074 (4)
C4	0.0214 (6)	0.0217 (6)	0.0224 (6)	−0.0069 (5)	−0.0014 (5)	−0.0067 (5)
C5	0.0201 (6)	0.0232 (6)	0.0181 (6)	−0.0013 (5)	−0.0011 (5)	−0.0077 (5)
C6	0.0221 (6)	0.0166 (5)	0.0174 (6)	0.0004 (4)	−0.0068 (5)	−0.0083 (4)
C7	0.0172 (6)	0.0234 (6)	0.0141 (6)	−0.0052 (5)	0.0017 (4)	−0.0085 (4)
C8	0.0206 (6)	0.0211 (6)	0.0199 (6)	−0.0015 (5)	−0.0023 (5)	−0.0111 (5)
C9	0.0208 (6)	0.0232 (6)	0.0216 (6)	−0.0042 (5)	−0.0015 (5)	−0.0111 (5)
C10	0.0269 (7)	0.0218 (6)	0.0258 (7)	−0.0041 (5)	−0.0040 (5)	−0.0115 (5)
C11	0.0348 (8)	0.0286 (7)	0.0441 (9)	−0.0095 (6)	−0.0049 (6)	−0.0189 (6)

O1—N1	1.2264 (12)	C5—C6	1.3878 (16)
O2—N1	1.2461 (12)	C5—H5	0.9500
O3—C3	1.3476 (13)	C7—C8	1.4948 (15)
O3—H3	0.872 (14)	C8—C9	1.5171 (16)
O4—C7	1.3678 (15)	C8—H8A	0.9900
O4—C6	1.4032 (12)	C8—H8B	0.9900
O5—C7	1.2019 (14)	C9—C10	1.5258 (14)
N1—C2	1.4508 (14)	C9—H9A	0.9900
C1—C6	1.3675 (15)	C9—H9B	0.9900
C1—C2	1.3956 (15)	C10—C11	1.5170 (18)
C1—H1	0.9500	C10—H10A	0.9900
C2—C3	1.3987 (16)	C10—H10B	0.9900
C3—C4	1.3984 (16)	C11—H11A	0.9800
C4—C5	1.3762 (16)	C11—H11B	0.9800
C4—H4	0.9500	C11—H11C	0.9800
C3—O3—H3	109.7 (10)	O4—C7—C8	110.77 (10)
C7—O4—C6	117.46 (9)	C7—C8—C9	113.82 (9)
O1—N1—O2	122.30 (9)	C7—C8—H8A	108.8
O1—N1—C2	119.42 (9)	C9—C8—H8A	108.8
O2—N1—C2	118.27 (9)	C7—C8—H8B	108.8
C6—C1—C2	118.66 (10)	C9—C8—H8B	108.8
C6—C1—H1	120.7	H8A—C8—H8B	107.7
C2—C1—H1	120.7	C8—C9—C10	111.43 (9)
C1—C2—C3	121.70 (9)	C8—C9—H9A	109.3
C1—C2—N1	117.19 (10)	C10—C9—H9A	109.3
C3—C2—N1	121.08 (10)	C8—C9—H9B	109.3
O3—C3—C4	116.78 (10)	C10—C9—H9B	109.3
O3—C3—C2	125.67 (10)	H9A—C9—H9B	108.0
C4—C3—C2	117.55 (10)	C11—C10—C9	113.11 (10)
C5—C4—C3	121.13 (11)	C11—C10—H10A	109.0
C5—C4—H4	119.4	C9—C10—H10A	109.0
C3—C4—H4	119.4	C11—C10—H10B	109.0
C4—C5—C6	119.68 (10)	C9—C10—H10B	109.0
C4—C5—H5	120.2	H10A—C10—H10B	107.8
C6—C5—H5	120.2	C10—C11—H11A	109.5
C1—C6—C5	121.27 (10)	C10—C11—H11B	109.5
C1—C6—O4	119.95 (10)	H11A—C11—H11B	109.5
C5—C6—O4	118.54 (9)	C10—C11—H11C	109.5
O5—C7—O4	122.35 (10)	H11A—C11—H11C	109.5
O5—C7—C8	126.85 (12)	H11B—C11—H11C	109.5
C6—C1—C2—C3	0.58 (18)	C2—C1—C6—C5	−1.16 (18)
C6—C1—C2—N1	−177.40 (10)	C2—C1—C6—O4	173.22 (10)
O1—N1—C2—C1	−0.25 (16)	C4—C5—C6—C1	0.80 (19)
O2—N1—C2—C1	179.25 (11)	C4—C5—C6—O4	−173.66 (11)
O1—N1—C2—C3	−178.24 (11)	C7—O4—C6—C1	83.13 (13)
O2—N1—C2—C3	1.26 (17)	C7—O4—C6—C5	−102.34 (13)
C1—C2—C3—O3	−178.86 (12)	C6—O4—C7—O5	−0.14 (15)
N1—C2—C3—O3	−0.96 (19)	C6—O4—C7—C8	177.99 (8)
C1—C2—C3—C4	0.34 (18)	O5—C7—C8—C9	−28.67 (16)
N1—C2—C3—C4	178.24 (11)	O4—C7—C8—C9	153.30 (9)
O3—C3—C4—C5	178.56 (11)	C7—C8—C9—C10	175.07 (9)
C2—C3—C4—C5	−0.72 (18)	C8—C9—C10—C11	164.72 (10)
C3—C4—C5—C6	0.17 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.872 (14)	1.871 (14)	2.6022 (13)	140.2 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.872 (14)	1.871 (14)	2.6022 (13)	140.2 (13)