(2-Methyl-3-nitro-phen-yl)methanol.

The asymmetric unit of the title compound, C(8)H(9)NO(3), contains two crystallographically independent mol-ecules, whose aromatic rings are oriented at a dihedral angle of 83.29 (3)°. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into chains.

Related literature

The title compound is an intermediate in the synthesis of the monomer 2-methyl-3-nitrobenzaldehyde, utilized to synthesize ergoline derivatives which have potential use in the treatment of Parkinson’s disease, see: Kozikowski et al. (1980 ▶). For a related structure, see: Wu et al. (1994 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H9NO3

M = 167.16

Monoclinic,

a = 13.601 (3) Å

b = 7.8650 (16) Å

c = 15.433 (3) Å

β = 92.73 (3)°

V = 1649.0 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.10 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 = 0.969, T max = 0.990

3123 measured reflections

2990 independent reflections

1783 reflections with I > 2σ(I)

R int = 0.020

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

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.189

S = 1.00

2990 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680902707X/hk2709sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902707X/hk2709Isup2.hkl

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

C8H9NO3	F(000) = 704
Mr = 167.16	Dx = 1.347 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 13.601 (3) Å	θ = 9–13°
b = 7.8650 (16) Å	µ = 0.10 mm−1
c = 15.433 (3) Å	T = 294 K
β = 92.73 (3)°	Block, colorless
V = 1649.0 (6) Å3	0.30 × 0.20 × 0.10 mm
Z = 8

Enraf–Nonius CAD-4 diffractometer	1783 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
graphite	θmax = 25.3°, θmin = 2.0°
ω/2θ scans	h = 0→16
Absorption correction: ψ scan (North et al., 1968)	k = 0→9
Tmin = 0.969, Tmax = 0.990	l = −18→18
3123 measured reflections	3 standard reflections every 120 min
2990 independent reflections	intensity decay: 1%

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.098P)2 + 0.3P] where P = (Fo2 + 2Fc2)/3
2990 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.31 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	0.16054 (17)	−0.8063 (3)	−0.23189 (13)	0.0674 (6)
H1A	0.1609	−0.7149	−0.2575	0.101*
O2	0.1306 (2)	−0.3449 (4)	0.12458 (19)	0.0991 (9)
O3	0.2061 (3)	−0.2898 (4)	0.0108 (2)	0.1103 (10)
O4	0.71669 (15)	0.0476 (3)	0.16390 (14)	0.0660 (6)
H4B	0.7457	−0.0431	0.1706	0.099*
O5	0.3487 (3)	−0.4236 (4)	0.2226 (2)	0.1256 (13)
O6	0.4004 (3)	−0.4885 (4)	0.0995 (2)	0.1141 (11)
N1	0.1592 (2)	−0.3846 (4)	0.0546 (2)	0.0673 (8)
N2	0.3911 (2)	−0.3892 (4)	0.1578 (2)	0.0730 (8)
C1	0.0769 (3)	−0.8143 (4)	−0.1800 (2)	0.0688 (9)
H1B	0.0515	−0.9296	−0.1809	0.083*
H1C	0.0258	−0.7405	−0.2048	0.083*
C2	0.1004 (2)	−0.7622 (4)	−0.0875 (2)	0.0537 (8)
C3	0.1075 (2)	−0.8874 (4)	−0.0244 (2)	0.0617 (8)
H3A	0.0977	−1.0001	−0.0410	0.074*
C4	0.1285 (2)	−0.8523 (4)	0.0614 (2)	0.0647 (9)
H4A	0.1324	−0.9392	0.1023	0.078*
C5	0.1437 (2)	−0.6856 (4)	0.0859 (2)	0.0606 (8)
H5A	0.1568	−0.6576	0.1439	0.073*
C6	0.1391 (2)	−0.5609 (4)	0.0230 (2)	0.0524 (7)
C7	0.1176 (2)	−0.5903 (4)	−0.06465 (19)	0.0507 (7)
C8	0.1098 (3)	−0.4514 (4)	−0.1320 (2)	0.0739 (10)
H8A	0.1235	−0.3436	−0.1049	0.111*
H8B	0.0445	−0.4502	−0.1584	0.111*
H8C	0.1565	−0.4720	−0.1756	0.111*
C9	0.6502 (3)	0.0372 (5)	0.0897 (2)	0.0699 (9)
H9A	0.6754	−0.0445	0.0492	0.084*
H9B	0.6471	0.1470	0.0611	0.084*
C10	0.5492 (2)	−0.0142 (4)	0.11181 (18)	0.0530 (8)
C11	0.4806 (3)	0.1136 (4)	0.1233 (2)	0.0635 (9)
H11A	0.4984	0.2258	0.1133	0.076*
C12	0.3874 (3)	0.0797 (4)	0.1490 (2)	0.0685 (9)
H12A	0.3434	0.1677	0.1579	0.082*
C13	0.3602 (2)	−0.0863 (4)	0.1612 (2)	0.0638 (9)
H13A	0.2974	−0.1124	0.1786	0.077*
C14	0.4266 (2)	−0.2128 (4)	0.14749 (19)	0.0546 (8)
C15	0.5225 (2)	−0.1851 (4)	0.12415 (18)	0.0530 (7)
C16	0.5962 (3)	−0.3269 (5)	0.1152 (3)	0.0820 (11)
H16A	0.5651	−0.4341	0.1255	0.123*
H16B	0.6502	−0.3111	0.1568	0.123*
H16C	0.6203	−0.3257	0.0578	0.123*

	U11	U22	U33	U12	U13	U23
O1	0.0856 (16)	0.0542 (13)	0.0632 (13)	0.0045 (12)	0.0132 (12)	0.0046 (10)
O2	0.109 (2)	0.094 (2)	0.095 (2)	−0.0099 (17)	0.0212 (17)	−0.0380 (17)
O3	0.147 (3)	0.0667 (18)	0.119 (2)	−0.0378 (18)	0.025 (2)	−0.0038 (16)
O4	0.0626 (13)	0.0569 (13)	0.0782 (15)	0.0068 (11)	−0.0007 (11)	0.0009 (11)
O5	0.160 (3)	0.108 (3)	0.110 (2)	−0.049 (2)	0.018 (2)	0.0217 (19)
O6	0.147 (3)	0.0529 (16)	0.143 (3)	−0.0101 (16)	0.009 (2)	−0.0303 (17)
N1	0.0624 (17)	0.0586 (18)	0.081 (2)	−0.0018 (15)	0.0003 (15)	−0.0078 (16)
N2	0.079 (2)	0.0530 (18)	0.086 (2)	−0.0051 (15)	−0.0099 (17)	0.0042 (17)
C1	0.070 (2)	0.067 (2)	0.069 (2)	−0.0005 (18)	0.0034 (17)	−0.0058 (18)
C2	0.0487 (16)	0.0512 (18)	0.0615 (18)	0.0024 (14)	0.0054 (14)	0.0001 (15)
C3	0.0614 (19)	0.0427 (17)	0.082 (2)	−0.0028 (15)	0.0089 (17)	0.0032 (16)
C4	0.065 (2)	0.058 (2)	0.071 (2)	0.0007 (16)	0.0051 (17)	0.0141 (17)
C5	0.0591 (18)	0.069 (2)	0.0537 (17)	−0.0004 (17)	−0.0001 (14)	0.0035 (16)
C6	0.0454 (16)	0.0469 (17)	0.0652 (19)	0.0016 (13)	0.0056 (13)	−0.0029 (15)
C7	0.0482 (16)	0.0456 (17)	0.0587 (18)	0.0029 (13)	0.0065 (13)	0.0034 (14)
C8	0.095 (3)	0.057 (2)	0.070 (2)	0.0078 (19)	0.0098 (19)	0.0105 (17)
C9	0.078 (2)	0.072 (2)	0.0598 (19)	−0.0006 (19)	0.0034 (17)	0.0053 (17)
C10	0.0611 (19)	0.0521 (18)	0.0451 (16)	0.0034 (15)	−0.0044 (13)	0.0012 (13)
C11	0.076 (2)	0.0417 (17)	0.071 (2)	0.0028 (16)	−0.0163 (17)	−0.0019 (15)
C12	0.062 (2)	0.051 (2)	0.091 (3)	0.0143 (17)	−0.0128 (18)	−0.0143 (17)
C13	0.0557 (18)	0.060 (2)	0.074 (2)	0.0022 (16)	−0.0072 (15)	−0.0117 (16)
C14	0.066 (2)	0.0386 (16)	0.0583 (18)	0.0020 (15)	−0.0084 (15)	−0.0021 (13)
C15	0.0636 (19)	0.0471 (17)	0.0475 (16)	0.0077 (15)	−0.0061 (13)	−0.0039 (13)
C16	0.079 (2)	0.065 (2)	0.103 (3)	0.0218 (19)	0.005 (2)	−0.008 (2)

O1—C1	1.423 (4)	C6—C7	1.390 (4)
O1—H1A	0.8200	C7—C8	1.508 (4)
O2—N1	1.207 (3)	C8—H8A	0.9600
O3—N1	1.208 (3)	C8—H8B	0.9600
O4—C9	1.427 (4)	C8—H8C	0.9600
O4—H4B	0.8200	C9—C10	1.487 (4)
O5—N2	1.209 (4)	C9—H9A	0.9700
O6—N2	1.203 (4)	C9—H9B	0.9700
N1—C6	1.491 (4)	C10—C11	1.388 (4)
N2—C14	1.480 (4)	C10—C15	1.408 (4)
C1—C2	1.505 (4)	C11—C12	1.372 (5)
C1—H1B	0.9700	C11—H11A	0.9300
C1—H1C	0.9700	C12—C13	1.373 (4)
C2—C3	1.385 (4)	C12—H12A	0.9300
C2—C7	1.414 (4)	C13—C14	1.367 (4)
C3—C4	1.369 (4)	C13—H13A	0.9300
C3—H3A	0.9300	C14—C15	1.387 (4)
C4—C5	1.378 (4)	C15—C16	1.510 (4)
C4—H4A	0.9300	C16—H16A	0.9600
C5—C6	1.379 (4)	C16—H16B	0.9600
C5—H5A	0.9300	C16—H16C	0.9600
C1—O1—H1A	109.5	H8A—C8—H8B	109.5
C9—O4—H4B	109.5	C7—C8—H8C	109.5
O2—N1—O3	122.8 (3)	H8A—C8—H8C	109.5
O2—N1—C6	118.2 (3)	H8B—C8—H8C	109.5
O3—N1—C6	119.0 (3)	O4—C9—C10	112.9 (3)
O5—N2—C14	118.0 (3)	O4—C9—H9A	109.0
O6—N2—O5	123.1 (3)	O4—C9—H9B	109.0
O6—N2—C14	118.7 (3)	C10—C9—H9A	109.0
O1—C1—C2	112.5 (3)	C10—C9—H9B	109.0
O1—C1—H1B	109.1	H9A—C9—H9B	107.8
O1—C1—H1C	109.1	C11—C10—C15	119.6 (3)
C2—C1—H1B	109.1	C11—C10—C9	117.8 (3)
C2—C1—H1C	109.1	C15—C10—C9	122.5 (3)
H1B—C1—H1C	107.8	C12—C11—C10	122.1 (3)
C3—C2—C7	120.0 (3)	C12—C11—H11A	118.9
C3—C2—C1	118.5 (3)	C10—C11—H11A	118.9
C7—C2—C1	121.5 (3)	C11—C12—C13	118.9 (3)
C4—C3—C2	122.7 (3)	C11—C12—H12A	120.5
C4—C3—H3A	118.6	C13—C12—H12A	120.5
C2—C3—H3A	118.6	C14—C13—C12	119.1 (3)
C3—C4—C5	118.7 (3)	C14—C13—H13A	120.5
C3—C4—H4A	120.7	C12—C13—H13A	120.5
C5—C4—H4A	120.7	C13—C14—C15	124.2 (3)
C4—C5—C6	118.8 (3)	C13—C14—N2	116.4 (3)
C4—C5—H5A	120.6	C15—C14—N2	119.4 (3)
C6—C5—H5A	120.6	C14—C15—C10	115.9 (3)
C5—C6—C7	124.6 (3)	C14—C15—C16	123.0 (3)
C5—C6—N1	115.4 (3)	C10—C15—C16	121.1 (3)
C7—C6—N1	120.0 (3)	C15—C16—H16A	109.5
C6—C7—C2	115.2 (3)	C15—C16—H16B	109.5
C6—C7—C8	123.7 (3)	H16A—C16—H16B	109.5
C2—C7—C8	121.0 (3)	C15—C16—H16C	109.5
C7—C8—H8A	109.5	H16A—C16—H16C	109.5
C7—C8—H8B	109.5	H16B—C16—H16C	109.5
O1—C1—C2—C3	−105.3 (3)	O4—C9—C10—C11	95.5 (3)
O1—C1—C2—C7	73.1 (4)	O4—C9—C10—C15	−82.3 (4)
C7—C2—C3—C4	1.7 (5)	C15—C10—C11—C12	1.9 (5)
C1—C2—C3—C4	−179.9 (3)	C9—C10—C11—C12	−175.9 (3)
C2—C3—C4—C5	−0.4 (5)	C10—C11—C12—C13	−1.9 (5)
C3—C4—C5—C6	−1.3 (5)	C11—C12—C13—C14	0.0 (5)
C4—C5—C6—C7	1.7 (5)	C12—C13—C14—C15	2.1 (5)
C4—C5—C6—N1	−178.4 (3)	C12—C13—C14—N2	−177.2 (3)
O2—N1—C6—C5	−36.1 (4)	O6—N2—C14—C13	126.6 (4)
O3—N1—C6—C5	141.4 (3)	O5—N2—C14—C13	−49.0 (4)
O2—N1—C6—C7	143.8 (3)	O6—N2—C14—C15	−52.8 (4)
O3—N1—C6—C7	−38.7 (4)	O5—N2—C14—C15	131.7 (4)
C5—C6—C7—C2	−0.4 (4)	C13—C14—C15—C10	−2.1 (4)
N1—C6—C7—C2	179.6 (3)	N2—C14—C15—C10	177.2 (3)
C5—C6—C7—C8	177.9 (3)	C13—C14—C15—C16	175.8 (3)
N1—C6—C7—C8	−2.0 (4)	N2—C14—C15—C16	−4.9 (5)
C3—C2—C7—C6	−1.3 (4)	C11—C10—C15—C14	0.1 (4)
C1—C2—C7—C6	−179.6 (3)	C9—C10—C15—C14	177.8 (3)
C3—C2—C7—C8	−179.7 (3)	C11—C10—C15—C16	−177.8 (3)
C1—C2—C7—C8	2.0 (4)	C9—C10—C15—C16	−0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O4i	0.82	1.97	2.725 (3)	153
O4—H4B···O1ii	0.82	1.95	2.706 (3)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O4i	0.82	1.97	2.725 (3)	153
O4—H4B⋯O1ii	0.82	1.95	2.706 (3)	153

Symmetry codes: (i) ; (ii) .