2-Methyl-4-nitro-phenol.

The mol-ecule of the title compound, C(7)H(7)NO(3), is nearly planar [maximum deviation 0.112 (3) Å for one of the notro O atoms]. In the crystal structure, inter-molecular O-H⋯O and C-H⋯O inter-actions link the mol-ecules into a three-dimensional network.

Related literature

For a related structure, see: Ahmed & Ashwini (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C7H7NO3

M = 153.14

Monoclinic,

a = 5.6210 (11) Å

b = 8.7420 (17) Å>

c = 14.300 (3) Å

β = 100.71 (3)°

V = 690.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 294 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.966, T max = 0.988

1378 measured reflections

1245 independent reflections

870 reflections with I > 2σ(I)

R int = 0.027

3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.181

S = 1.01

1245 reflections

102 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809018716/hk2688sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018716/hk2688Isup2.hkl

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

C7H7NO3	F(000) = 320
Mr = 153.14	Dx = 1.473 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 5.6210 (11) Å	θ = 9–13°
b = 8.7420 (17) Å	µ = 0.12 mm−1
c = 14.300 (3) Å	T = 294 K
β = 100.71 (3)°	Block, colorless
V = 690.4 (2) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	870 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
graphite	θmax = 25.3°, θmin = 2.7°
ω/2θ scans	h = 0→6
Absorption correction: ψ scan (North et al., 1968)	k = 0→10
Tmin = 0.966, Tmax = 0.988	l = −17→16
1378 measured reflections	3 standard reflections every 120 min
1245 independent reflections	intensity decay: 1%

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)] = 0.054	H-atom parameters constrained
wR(F2) = 0.181	w = 1/[σ2(Fo2) + (0.08P)2 + 0.74P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
1245 reflections	Δρmax = 0.25 e Å−3
102 parameters	Δρmin = −0.24 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: 0.017 (4)

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	−0.3440 (5)	0.6807 (3)	0.9304 (2)	0.0769 (9)
O2	−0.0576 (5)	0.7542 (3)	0.8605 (2)	0.0682 (8)
O3	0.0480 (4)	0.0536 (3)	0.81980 (17)	0.0567 (7)
H3A	−0.0372	−0.0079	0.8417	0.085*
N	−0.1770 (5)	0.6536 (3)	0.8896 (2)	0.0490 (8)
C1	0.0652 (6)	0.4640 (4)	0.8248 (2)	0.0478 (9)
H1A	0.1525	0.5429	0.8034	0.057*
C2	0.1146 (6)	0.3143 (4)	0.8076 (2)	0.0487 (9)
H2A	0.2352	0.2908	0.7734	0.058*
C3	−0.0137 (6)	0.1979 (4)	0.8410 (2)	0.0417 (8)
C4	−0.1941 (5)	0.2284 (3)	0.8932 (2)	0.0410 (8)
C5	−0.2457 (6)	0.3796 (4)	0.9085 (2)	0.0415 (8)
H5A	−0.3678	0.4038	0.9418	0.050*
C6	−0.1175 (5)	0.4950 (4)	0.8747 (2)	0.0413 (8)
C7	−0.3278 (6)	0.1019 (4)	0.9313 (3)	0.0531 (9)
H7A	−0.2143	0.0360	0.9707	0.080*
H7B	−0.4172	0.0441	0.8793	0.080*
H7C	−0.4375	0.1443	0.9684	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.093 (2)	0.0485 (16)	0.104 (2)	0.0137 (14)	0.0576 (18)	−0.0051 (15)
O2	0.0861 (19)	0.0303 (13)	0.097 (2)	−0.0030 (12)	0.0392 (16)	0.0063 (13)
O3	0.0661 (15)	0.0341 (13)	0.0802 (17)	0.0000 (11)	0.0405 (13)	−0.0053 (11)
N	0.0594 (18)	0.0337 (15)	0.0567 (17)	0.0039 (13)	0.0180 (14)	0.0005 (13)
C1	0.0539 (19)	0.0371 (17)	0.059 (2)	−0.0036 (14)	0.0281 (17)	0.0044 (15)
C2	0.0496 (19)	0.0413 (18)	0.063 (2)	−0.0036 (15)	0.0302 (17)	−0.0024 (16)
C3	0.0438 (17)	0.0339 (15)	0.0503 (18)	−0.0019 (14)	0.0168 (14)	−0.0029 (14)
C4	0.0389 (16)	0.0397 (17)	0.0473 (18)	−0.0032 (13)	0.0156 (14)	−0.0012 (14)
C5	0.0403 (16)	0.0407 (17)	0.0469 (17)	0.0021 (14)	0.0171 (14)	0.0005 (14)
C6	0.0461 (17)	0.0312 (16)	0.0500 (18)	0.0009 (13)	0.0177 (14)	−0.0006 (13)
C7	0.054 (2)	0.045 (2)	0.068 (2)	−0.0034 (15)	0.0285 (17)	0.0007 (16)

O3—C3	1.357 (4)	C2—H2A	0.9300
O3—H3A	0.8200	C3—C4	1.393 (4)
N—O1	1.217 (3)	C4—C5	1.379 (4)
N—O2	1.225 (4)	C4—C7	1.496 (4)
N—C6	1.451 (4)	C5—C6	1.379 (4)
C1—C2	1.370 (5)	C5—H5A	0.9300
C1—C6	1.382 (4)	C7—H7A	0.9600
C1—H1A	0.9300	C7—H7B	0.9600
C2—C3	1.382 (4)	C7—H7C	0.9600
C3—O3—H3A	109.5	C5—C4—C7	121.1 (3)
O1—N—O2	122.9 (3)	C3—C4—C7	121.2 (3)
O1—N—C6	118.4 (3)	C6—C5—C4	120.5 (3)
O2—N—C6	118.7 (3)	C6—C5—H5A	119.8
C2—C1—C6	118.4 (3)	C4—C5—H5A	119.8
C2—C1—H1A	120.8	C5—C6—C1	121.6 (3)
C6—C1—H1A	120.8	C5—C6—N	119.9 (3)
C1—C2—C3	120.4 (3)	C1—C6—N	118.5 (3)
C1—C2—H2A	119.8	C4—C7—H7A	109.5
C3—C2—H2A	119.8	C4—C7—H7B	109.5
O3—C3—C2	115.9 (3)	H7A—C7—H7B	109.5
O3—C3—C4	122.7 (3)	C4—C7—H7C	109.5
C2—C3—C4	121.5 (3)	H7A—C7—H7C	109.5
C5—C4—C3	117.7 (3)	H7B—C7—H7C	109.5
O1—N—C6—C5	−1.5 (5)	O3—C3—C4—C5	−178.4 (3)
O2—N—C6—C5	178.6 (3)	C2—C3—C4—C5	1.8 (5)
O1—N—C6—C1	177.3 (3)	O3—C3—C4—C7	1.4 (5)
O2—N—C6—C1	−2.6 (5)	C2—C3—C4—C7	−178.3 (3)
C6—C1—C2—C3	−1.0 (5)	C3—C4—C5—C6	−1.5 (5)
C2—C1—C6—C5	1.2 (5)	C7—C4—C5—C6	178.6 (3)
C2—C1—C6—N	−177.5 (3)	C4—C5—C6—C1	0.0 (5)
C1—C2—C3—O3	179.7 (3)	C4—C5—C6—N	178.8 (3)
C1—C2—C3—C4	−0.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2i	0.82	2.10	2.770 (4)	138
C7—H7C···O1ii	0.96	2.57	3.505 (5)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2i	0.82	2.10	2.770 (4)	138
C7—H7C⋯O1ii	0.96	2.57	3.505 (5)	165

Symmetry codes: (i) ; (ii) .