Methyl 2-hydr-oxy-3-nitro-benzoate.

The title compound, C(8)H(7)NO(5), assumes an approximately planar mol-ecular structure with an intra-molecular O-H⋯O hydrogen bond between the hydr-oxy and carboxyl-ate groups. Weak inter-molecular C-H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For the properties of 2-hydroxy­benzoyl compounds, see: Konopacka et al. (2005 ▶); Sonar et al. (2007 ▶); Willian & Layne (2001 ▶); Huang et al. (1996 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H7NO5

M = 197.15

Monoclinic,

a = 7.6120 (10) Å

b = 11.716 (2) Å

c = 9.656 (2) Å

β = 101.830 (10)°

V = 842.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 291 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

4045 measured reflections

1473 independent reflections

965 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.110

S = 1.02

1655 reflections

129 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.40 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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024301/xu2532sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024301/xu2532Isup2.hkl

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

C8H7NO5	F(000) = 408
Mr = 197.15	Dx = 1.554 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1211 reflections
a = 7.612 (1) Å	θ = 2.7–22.6°
b = 11.716 (2) Å	µ = 0.13 mm−1
c = 9.656 (2) Å	T = 291 K
β = 101.83 (1)°	Block, yellow
V = 842.9 (3) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	965 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.046
graphite	θmax = 26.0°, θmin = 2.7°
φ and ω scans	h = −8→9
4045 measured reflections	k = −13→13
1473 independent reflections	l = −11→6

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)] = 0.055	H-atom parameters constrained
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.02P)2 + 0.55P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
1655 reflections	Δρmax = 0.48 e Å−3
129 parameters	Δρmin = −0.40 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.010 (3)

Experimental. 1H-NMR (CDCl3, 500 MHz): δ4.03 (s, 3 H), 7.20(s, 1 H), 8.15-8.19 (d, 2 H), 12.02 (s, 1 H).

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
C3	0.6545 (3)	0.9162 (2)	−0.0890 (2)	0.0465 (6)
C4	0.6080 (3)	0.8030 (2)	−0.1125 (3)	0.0541 (7)
H4A	0.5248	0.7822	−0.1931	0.065*
C5	0.6836 (4)	0.7212 (2)	−0.0176 (3)	0.0581 (8)
H5A	0.6523	0.6448	−0.0337	0.070*
C6	0.8059 (3)	0.7525 (2)	0.1011 (3)	0.0504 (7)
H6A	0.8577	0.6966	0.1649	0.060*
C1	0.8541 (3)	0.8654 (2)	0.1281 (2)	0.0433 (6)
C2	0.7769 (3)	0.9507 (2)	0.0320 (2)	0.0449 (6)
C7	0.9867 (3)	0.8997 (2)	0.2543 (3)	0.0499 (7)
C8	1.1859 (4)	0.8424 (2)	0.4632 (3)	0.0654 (9)
H8C	1.2856	0.8819	0.4384	0.098*
H8B	1.2277	0.7740	0.5140	0.098*
H8A	1.1297	0.8907	0.5217	0.098*
N1	0.5694 (4)	0.9981 (2)	−0.1954 (3)	0.0726 (8)
O2	0.6026 (3)	1.09798 (19)	−0.1803 (2)	0.0830 (7)
O3	0.4677 (4)	0.96270 (19)	−0.2983 (2)	0.1045 (9)
O1	0.8187 (3)	1.06068 (13)	0.05425 (19)	0.0651 (6)
H1A	0.9073	1.0676	0.1402	0.098*
O4	1.0286 (3)	0.99828 (15)	0.2831 (2)	0.0692 (6)
O5	1.0566 (2)	0.81316 (14)	0.33514 (18)	0.0564 (5)

	U11	U22	U33	U12	U13	U23
C3	0.0456 (15)	0.0474 (15)	0.0452 (15)	0.0024 (12)	0.0064 (12)	0.0044 (12)
C4	0.0541 (17)	0.0566 (18)	0.0479 (16)	−0.0064 (14)	0.0016 (13)	−0.0055 (13)
C5	0.0686 (19)	0.0408 (15)	0.0602 (17)	−0.0089 (14)	0.0021 (15)	−0.0062 (13)
C6	0.0570 (17)	0.0389 (14)	0.0523 (16)	0.0003 (12)	0.0043 (13)	0.0024 (12)
C1	0.0445 (14)	0.0380 (14)	0.0454 (14)	0.0009 (11)	0.0047 (11)	−0.0006 (11)
C2	0.0461 (15)	0.0383 (14)	0.0490 (15)	−0.0006 (12)	0.0064 (12)	−0.0027 (12)
C7	0.0510 (16)	0.0417 (15)	0.0537 (16)	0.0010 (13)	0.0032 (12)	0.0006 (13)
C8	0.0645 (19)	0.0666 (18)	0.0539 (17)	−0.0020 (15)	−0.0143 (14)	0.0017 (14)
N1	0.088 (2)	0.0614 (17)	0.0573 (16)	0.0015 (15)	−0.0116 (14)	0.0065 (14)
O2	0.1039 (18)	0.0617 (14)	0.0704 (14)	0.0079 (13)	−0.0123 (12)	0.0118 (11)
O3	0.130 (2)	0.0832 (17)	0.0741 (16)	−0.0058 (15)	−0.0405 (15)	0.0098 (13)
O1	0.0776 (14)	0.0355 (10)	0.0703 (13)	−0.0033 (9)	−0.0130 (10)	0.0026 (9)
O4	0.0805 (14)	0.0404 (11)	0.0720 (13)	−0.0043 (10)	−0.0188 (11)	−0.0055 (9)
O5	0.0603 (12)	0.0469 (11)	0.0532 (11)	−0.0018 (9)	−0.0089 (9)	0.0030 (9)

C3—C4	1.380 (3)	C2—O1	1.334 (3)
C3—C2	1.396 (3)	C7—O4	1.215 (3)
C3—N1	1.457 (3)	C7—O5	1.323 (3)
C4—C5	1.369 (3)	C8—O5	1.455 (3)
C4—H4A	0.9300	C8—H8C	0.9600
C5—C6	1.371 (3)	C8—H8B	0.9600
C5—H5A	0.9300	C8—H8A	0.9600
C6—C1	1.383 (3)	N1—O2	1.200 (3)
C6—H6A	0.9300	N1—O3	1.201 (3)
C1—C2	1.408 (3)	O1—H1A	0.9600
C1—C7	1.470 (3)
C4—C3—C2	121.4 (2)	O1—C2—C1	121.7 (2)
C4—C3—N1	117.0 (2)	C3—C2—C1	117.6 (2)
C2—C3—N1	121.6 (2)	O4—C7—O5	122.6 (2)
C5—C4—C3	120.3 (2)	O4—C7—C1	123.6 (2)
C5—C4—H4A	119.8	O5—C7—C1	113.8 (2)
C3—C4—H4A	119.8	O5—C8—H8C	109.5
C4—C5—C6	119.5 (2)	O5—C8—H8B	109.5
C4—C5—H5A	120.3	H8C—C8—H8B	109.5
C6—C5—H5A	120.3	O5—C8—H8A	109.5
C5—C6—C1	121.5 (2)	H8C—C8—H8A	109.5
C5—C6—H6A	119.2	H8B—C8—H8A	109.5
C1—C6—H6A	119.2	O2—N1—O3	121.4 (2)
C6—C1—C2	119.7 (2)	O2—N1—C3	120.2 (2)
C6—C1—C7	121.9 (2)	O3—N1—C3	118.3 (3)
C2—C1—C7	118.4 (2)	C2—O1—H1A	108.9
O1—C2—C3	120.7 (2)	C7—O5—C8	116.16 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O4	0.96	1.70	2.554 (2)	146
C4—H4A···O2i	0.93	2.57	3.321 (3)	138
C6—H6A···O4ii	0.93	2.49	3.336 (3)	151
C8—H8B···O1ii	0.96	2.59	3.305 (3)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O4	0.96	1.70	2.554 (2)	146
C4—H4A⋯O2i	0.93	2.57	3.321 (3)	138
C6—H6A⋯O4ii	0.93	2.49	3.336 (3)	151
C8—H8B⋯O1ii	0.96	2.59	3.305 (3)	131

Symmetry codes: (i) ; (ii) .