(2-Methyl-3-nitro­phen­yl)methanol

Zhang, J.; Chen, Y.; Wang, X.

doi:10.1107/S160053680902707X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1925

doi:10.1107/S160053680902707X

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(2-Methyl-3-nitrophenyl)methanol

Jian-hong Zhang,^a You-sheng Chen ^a and Xi Wang ^a ^*

^aDepartment of Pharmacy, Guangdong Food and Drug Vocational College, Guangzhou 510520, People's Republic of China
^*Correspondence e-mail: njjhs@163.com

(Received 9 June 2009; accepted 10 July 2009; online 18 July 2009)

The asymmetric unit of the title compound, C₈H₉NO₃, contains two crystallographically independent molecules, whose aromatic rings are oriented at a dihedral angle of 83.29 (3)°. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link the molecules 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_r = 167.16
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.061
wR(F²) = 0.189
S = 1.00
2990 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.31 e Å⁻³

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) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y-1, -z.

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).

Supporting information

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

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

checkCIF report

Comment top

The tittle compound is an important intermediate used to synthesize the monomer 2-methyl-3-nitrobenzaldehyde, which can be utilized to synthesize ergoline derivatives and it has been reported to have some useful physiological and pharmacological functions to parkinson's disease (Kozikowski et al., 1980). We report herein the crystal structure of the title compound, which is of interest to us in the field.

The asymmetric unit of the title compound contains two crystallographically independent molecules (Fig. 1), in which the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C2-C7) and B (C10-C15) are, of course, planar. The dihedral angle between them is 83.29 (3)°. Atoms N1, C1, C8 and N2, C9, C16 are -0.006 (3), 0.029 (3), -0.022 (3) and 0.077 (3), -0.075 (3), -0.076 (3) Å away from the adjacent ring planes, respectively.

In the crystal structure, intermolecular O-H···O hydrogen bonds (Table 1) link the molecules into chains (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For general background, see: Kozikowski et al. (1980). For a related structure, see: Wu et al. (1994). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared according to a literature method (Wu et al., 1994). Crystals suitable for X-ray analysis were obtained by slow evaporation of methanol for about 20 d.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); 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).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

(2-Methyl-3-nitrophenyl)methanol top

Crystal data top

C₈H₉NO₃	F(000) = 704
M_r = 167.16	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.098P)² + 0.3P] where P = (F_o² + 2F_c²)/3
2990 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₈H₉NO₃	V = 1649.0 (6) Å³
M_r = 167.16	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.601 (3) Å	µ = 0.10 mm⁻¹
b = 7.8650 (16) Å	T = 294 K
c = 15.433 (3) Å	0.30 × 0.20 × 0.10 mm
β = 92.73 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1783 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.020
T_min = 0.969, T_max = 0.990	3 standard reflections every 120 min
3123 measured reflections	intensity decay: 1%
2990 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.189	H-atom parameters constrained
S = 1.00	Δρ_max = 0.29 e Å⁻³
2990 reflections	Δρ_min = −0.31 e Å⁻³
217 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y−1/2, z−1/2; (ii) −x+1, −y−1, −z.

Experimental details

Crystal data
Chemical formula	C₈H₉NO₃
M_r	167.16
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	13.601 (3), 7.8650 (16), 15.433 (3)
β (°)	92.73 (3)
V (Å³)	1649.0 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.969, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	3123, 2990, 1783
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.189, 1.00
No. of reflections	2990
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.31

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y−1/2, z−1/2; (ii) −x+1, −y−1, −z.

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

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