Methyl 4-amino-3-methyl-benzoate.

In the mol-ecule of the title compound, C(9)H(11)NO(2), the methyl C and amino N atoms bonded to the benzene ring lie in the ring plane. Intra-molecular C-H⋯O hydrogen bonding results in the formation of a five-membered planar ring, which is oriented at a dihedral angle of 2.73 (3)° with respect to the benzene ring, so they are nearly coplanar. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains elongated along the c axis and stacked along the b axis.

Related literature

For related literature, see: Ries et al. (1993 ▶); Engeli et al. (2000 ▶); Kintscher et al. (2004 ▶); Goossens et al. (2003 ▶); Kurtz et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C9H11NO2

M = 165.19

Monoclinic,

a = 7.5670 (15) Å

b = 6.1080 (12) Å

c = 18.127 (4) Å

β = 98.14 (3)°

V = 829.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 294 (2) K

0.40 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.963, T max = 0.981

1747 measured reflections

1620 independent reflections

1079 reflections with I > 2σ(I)

R int = 0.022

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.188

S = 1.04

1620 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.27 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808006223/hk2431sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006223/hk2431Isup2.hkl

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

C9H11NO2	F000 = 352
Mr = 165.19	Dx = 1.323 Mg m−3
Monoclinic, P21/c	Melting point: 391(2) K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 7.5670 (15) Å	Cell parameters from 25 reflections
b = 6.1080 (12) Å	θ = 9–13º
c = 18.127 (4) Å	µ = 0.09 mm−1
β = 98.14 (3)º	T = 294 (2) K
V = 829.4 (3) Å3	Block, colorless
Z = 4	0.40 × 0.30 × 0.20 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.022
Radiation source: fine-focus sealed tube	θmax = 26.0º
Monochromator: graphite	θmin = 2.3º
T = 294(2) K	h = −9→9
ω/2θ scans	k = 0→7
Absorption correction: ψ scan(North et al., 1968)	l = 0→22
Tmin = 0.963, Tmax = 0.981	3 standard reflections
1747 measured reflections	every 200 reflections
1620 independent reflections	intensity decay: none
1079 reflections with I > 2σ(I)

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)] = 0.053	H-atom parameters constrained
wR(F2) = 0.188	w = 1/[σ2(Fo2) + (0.06P)2 + 1.3P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
1620 reflections	Δρmax = 0.25 e Å−3
109 parameters	Δρmin = −0.27 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
N	0.8206 (4)	0.4908 (5)	0.17914 (15)	0.0570 (8)
H0A	0.8716	0.6166	0.1792	0.068*
H0B	0.7811	0.4279	0.1376	0.068*
O1	0.6922 (3)	−0.1169 (4)	0.44629 (12)	0.0549 (7)
O2	0.8163 (4)	0.1644 (4)	0.51362 (13)	0.0621 (8)
C1	0.6852 (5)	−0.2393 (6)	0.51341 (18)	0.0561 (10)
H1A	0.6303	−0.3788	0.5012	0.084*
H1B	0.6164	−0.1599	0.5451	0.084*
H1C	0.8041	−0.2610	0.5388	0.084*
C2	0.7641 (4)	0.0832 (5)	0.45389 (18)	0.0440 (8)
C3	0.7726 (4)	0.1877 (5)	0.38130 (17)	0.0404 (7)
C4	0.7052 (4)	0.0892 (5)	0.31364 (17)	0.0423 (8)
H4A	0.6496	−0.0464	0.3145	0.051*
C5	0.7176 (4)	0.1847 (5)	0.24532 (17)	0.0405 (8)
C6	0.8021 (4)	0.3903 (5)	0.24530 (17)	0.0414 (7)
C7	0.8662 (4)	0.4927 (5)	0.31251 (18)	0.0450 (8)
H7A	0.9196	0.6297	0.3120	0.054*
C8	0.8517 (4)	0.3940 (5)	0.37935 (18)	0.0427 (8)
H8A	0.8947	0.4649	0.4237	0.051*
C9	0.6433 (5)	0.0725 (6)	0.17397 (18)	0.0525 (9)
H9A	0.5906	−0.0644	0.1851	0.079*
H9B	0.7377	0.0463	0.1448	0.079*
H9C	0.5541	0.1639	0.1464	0.079*

	U11	U22	U33	U12	U13	U23
N	0.076 (2)	0.0464 (17)	0.0479 (17)	−0.0106 (16)	0.0050 (15)	0.0071 (14)
O1	0.0748 (17)	0.0429 (13)	0.0455 (13)	−0.0097 (13)	0.0031 (11)	0.0032 (11)
O2	0.090 (2)	0.0538 (16)	0.0409 (13)	−0.0084 (14)	0.0053 (13)	−0.0040 (12)
C1	0.076 (3)	0.048 (2)	0.0449 (19)	−0.0029 (19)	0.0100 (17)	0.0037 (16)
C2	0.0489 (19)	0.0416 (18)	0.0418 (17)	0.0019 (16)	0.0079 (14)	−0.0005 (15)
C3	0.0425 (17)	0.0373 (17)	0.0414 (17)	0.0040 (14)	0.0058 (13)	−0.0029 (14)
C4	0.0430 (18)	0.0349 (17)	0.0479 (18)	−0.0003 (14)	0.0021 (14)	−0.0008 (14)
C5	0.0419 (18)	0.0344 (16)	0.0435 (17)	0.0038 (14)	0.0003 (13)	−0.0020 (14)
C6	0.0448 (18)	0.0325 (16)	0.0468 (17)	0.0050 (14)	0.0065 (14)	0.0022 (14)
C7	0.0458 (19)	0.0327 (16)	0.056 (2)	−0.0036 (14)	0.0061 (15)	−0.0014 (15)
C8	0.0477 (18)	0.0372 (17)	0.0434 (17)	0.0030 (15)	0.0071 (13)	−0.0067 (14)
C9	0.057 (2)	0.051 (2)	0.0469 (19)	−0.0055 (17)	−0.0031 (16)	−0.0022 (16)

N—C6	1.372 (4)	C4—C5	1.384 (4)
N—H0A	0.8600	C4—H4A	0.9300
N—H0B	0.8600	C5—C6	1.410 (4)
O1—C2	1.336 (4)	C5—C9	1.501 (4)
O1—C1	1.435 (4)	C6—C7	1.394 (4)
C1—H1A	0.9600	C7—C8	1.372 (4)
C1—H1B	0.9600	C7—H7A	0.9300
C1—H1C	0.9600	C8—H8A	0.9300
O2—C2	1.206 (4)	C9—H9A	0.9600
C2—C3	1.472 (4)	C9—H9B	0.9600
C3—C4	1.396 (4)	C9—H9C	0.9600
C3—C8	1.398 (4)
C6—N—H0A	120.0	C4—C5—C6	117.6 (3)
C6—N—H0B	120.0	C4—C5—C9	120.9 (3)
H0A—N—H0B	120.0	C6—C5—C9	121.4 (3)
C2—O1—C1	116.9 (3)	N—C6—C7	119.9 (3)
O1—C1—H1A	109.5	N—C6—C5	120.1 (3)
O1—C1—H1B	109.5	C7—C6—C5	120.1 (3)
H1A—C1—H1B	109.5	C8—C7—C6	120.9 (3)
O1—C1—H1C	109.5	C8—C7—H7A	119.5
H1A—C1—H1C	109.5	C6—C7—H7A	119.5
H1B—C1—H1C	109.5	C7—C8—C3	120.4 (3)
O2—C2—O1	123.1 (3)	C7—C8—H8A	119.8
O2—C2—C3	125.0 (3)	C3—C8—H8A	119.8
O1—C2—C3	111.9 (3)	C5—C9—H9A	109.5
C4—C3—C8	118.1 (3)	C5—C9—H9B	109.5
C4—C3—C2	122.8 (3)	H9A—C9—H9B	109.5
C8—C3—C2	119.1 (3)	C5—C9—H9C	109.5
C5—C4—C3	122.8 (3)	H9A—C9—H9C	109.5
C5—C4—H4A	118.6	H9B—C9—H9C	109.5
C3—C4—H4A	118.6
C1—O1—C2—O2	−2.4 (5)	C4—C5—C6—N	179.0 (3)
C1—O1—C2—C3	177.0 (3)	C9—C5—C6—N	−1.1 (5)
O2—C2—C3—C4	−178.0 (3)	C4—C5—C6—C7	−1.4 (4)
O1—C2—C3—C4	2.7 (4)	C9—C5—C6—C7	178.5 (3)
O2—C2—C3—C8	2.2 (5)	N—C6—C7—C8	−179.0 (3)
O1—C2—C3—C8	−177.2 (3)	C5—C6—C7—C8	1.3 (5)
C8—C3—C4—C5	1.7 (5)	C6—C7—C8—C3	0.3 (5)
C2—C3—C4—C5	−178.2 (3)	C4—C3—C8—C7	−1.7 (5)
C3—C4—C5—C6	−0.1 (5)	C2—C3—C8—C7	178.1 (3)
C3—C4—C5—C9	180.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O1	0.93	2.40	2.728 (4)	100
N—H0B···O2i	0.86	2.37	3.142 (3)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O1	0.93	2.40	2.728 (4)	100
N—H0B⋯O2i	0.86	2.37	3.142 (3)	150

Symmetry code: (i) .