Ethyl 4-amino-3-methyl-benzoate.

The asymmetric unit of the title compound, C(10)H(13)NO(2), contains two mol-ecules which are linked via an N-H⋯N hydrogen bonds to form a dimer. These dimers are further linked via N-H⋯O inter-molecular hydrogen bonds.

Related literature

For related literature, see: Baraldi et al. (1999 ▶, 2000 ▶, 2003 ▶, 2007 ▶); Wang et al. (2003 ▶); Zaffaroni et al. (2002 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H13NO2

M = 179.21

Triclinic,

a = 8.0110 (16) Å

b = 8.7030 (17) Å

c = 15.835 (3) Å

α = 90.78 (3)°

β = 95.13 (3)°

γ = 114.34 (3)°

V = 1000.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 (2) 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 = 0.975, T max = 0.991

3874 measured reflections

3594 independent reflections

2146 reflections with I > 2σ(I)

R int = 0.052

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.176

S = 1.02

3594 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.23 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808005989/er2050sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005989/er2050Isup2.hkl

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

C10H13NO2	Z = 4
Mr = 179.21	F000 = 384
Triclinic, P1	Dx = 1.190 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.0110 (16) Å	Cell parameters from 25 reflections
b = 8.7030 (17) Å	θ = 10–14º
c = 15.835 (3) Å	µ = 0.08 mm−1
α = 90.78 (3)º	T = 298 (2) K
β = 95.13 (3)º	Block, colorless
γ = 114.34 (3)º	0.30 × 0.20 × 0.10 mm
V = 1000.3 (3) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.052
Radiation source: fine-focus sealed tube	θmax = 25.2º
Monochromator: graphite	θmin = 1.3º
T = 298(2) K	h = −9→9
ω/2θ scans	k = −10→10
Absorption correction: ψ scan(North et al., 1968)	l = 0→18
Tmin = 0.975, Tmax = 0.991	3 standard reflections
3874 measured reflections	every 200 reflections
3594 independent reflections	intensity decay: none
2146 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)] = 0.075	H-atom parameters constrained
wR(F2) = 0.177	w = 1/[σ2(Fo2) + (0.04P)2 + 1.2P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3594 reflections	Δρmax = 0.23 e Å−3
235 parameters	Δρmin = −0.22 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
O1	1.2476 (4)	0.4839 (3)	1.01662 (15)	0.0684 (7)
O2	1.2577 (4)	0.5912 (3)	0.88836 (15)	0.0742 (8)
N1	0.5942 (5)	−0.1423 (4)	0.8227 (2)	0.0872 (11)
H1A	0.5484	−0.2192	0.8580	0.105*
H1B	0.5509	−0.1604	0.7701	0.105*
C1	1.4390 (7)	0.6205 (6)	1.1432 (2)	0.0884 (13)
H1C	1.5389	0.7220	1.1674	0.133*
H1D	1.4718	0.5267	1.1505	0.133*
H1E	1.3311	0.6012	1.1712	0.133*
C2	1.3999 (6)	0.6384 (5)	1.0501 (2)	0.0695 (10)
H2A	1.3681	0.7338	1.0420	0.083*
H2B	1.5077	0.6571	1.0211	0.083*
C3	1.1842 (5)	0.4730 (4)	0.9338 (2)	0.0549 (8)
C4	1.0343 (5)	0.3145 (4)	0.9073 (2)	0.0514 (8)
C5	0.9506 (5)	0.1886 (4)	0.9638 (2)	0.0620 (10)
H5A	0.9932	0.2072	1.0212	0.074*
C6	0.8093 (5)	0.0413 (4)	0.9358 (2)	0.0629 (10)
H6A	0.7590	−0.0410	0.9743	0.075*
C7	0.7362 (5)	0.0087 (4)	0.8503 (2)	0.0607 (9)
C8	0.8176 (5)	0.1308 (4)	0.7910 (2)	0.0579 (9)
C9	0.9597 (5)	0.2792 (4)	0.8216 (2)	0.0537 (8)
H9A	1.0103	0.3620	0.7834	0.064*
C10	0.7439 (6)	0.0996 (5)	0.6984 (2)	0.0790 (12)
H10A	0.8184	0.1926	0.6672	0.119*
H10B	0.6192	0.0889	0.6924	0.119*
H10C	0.7471	−0.0026	0.6767	0.119*
O3	0.2589 (4)	0.2954 (3)	0.47872 (15)	0.0695 (7)
O4	0.1772 (4)	0.3743 (3)	0.59841 (17)	0.0836 (9)
N2	0.2153 (5)	−0.3189 (4)	0.69728 (19)	0.0828 (11)
H2C	0.1979	−0.3380	0.7496	0.099*
H2D	0.2337	−0.3903	0.6656	0.099*
C11	0.3055 (7)	0.4392 (6)	0.3509 (3)	0.0990 (15)
H11A	0.3072	0.5370	0.3229	0.149*
H11B	0.2152	0.3391	0.3204	0.149*
H11C	0.4248	0.4375	0.3523	0.149*
C12	0.2570 (6)	0.4456 (5)	0.4406 (2)	0.0764 (11)
H12A	0.3465	0.5466	0.4722	0.092*
H12B	0.1360	0.4461	0.4403	0.092*
C13	0.2119 (5)	0.2726 (5)	0.5596 (2)	0.0608 (9)
C14	0.2194 (5)	0.1199 (4)	0.59291 (19)	0.0543 (8)
C15	0.1854 (5)	0.0871 (4)	0.6782 (2)	0.0545 (8)
H15A	0.1632	0.1649	0.7108	0.065*
C16	0.1840 (5)	−0.0559 (4)	0.7146 (2)	0.0549 (8)
C17	0.2137 (5)	−0.1753 (4)	0.6644 (2)	0.0597 (9)
C18	0.2476 (6)	−0.1425 (5)	0.5793 (2)	0.0682 (11)
H18A	0.2686	−0.2200	0.5458	0.082*
C19	0.2499 (5)	0.0029 (5)	0.5451 (2)	0.0660 (10)
H19A	0.2724	0.0221	0.4887	0.079*
C20	0.1455 (6)	−0.0876 (5)	0.8067 (2)	0.0768 (12)
H20A	0.1279	0.0055	0.8312	0.115*
H20B	0.2479	−0.0986	0.8379	0.115*
H20C	0.0363	−0.1897	0.8089	0.115*

	U11	U22	U33	U12	U13	U23
O1	0.0901 (18)	0.0660 (16)	0.0515 (14)	0.0347 (14)	0.0056 (13)	0.0157 (12)
O2	0.100 (2)	0.0594 (15)	0.0596 (16)	0.0282 (14)	0.0118 (14)	0.0263 (13)
N1	0.099 (3)	0.072 (2)	0.078 (2)	0.021 (2)	0.013 (2)	0.0202 (18)
C1	0.114 (4)	0.099 (3)	0.063 (3)	0.059 (3)	−0.010 (2)	−0.008 (2)
C2	0.090 (3)	0.060 (2)	0.067 (2)	0.040 (2)	0.000 (2)	0.0075 (19)
C3	0.068 (2)	0.055 (2)	0.051 (2)	0.0334 (18)	0.0094 (17)	0.0118 (16)
C4	0.068 (2)	0.0485 (19)	0.0467 (18)	0.0319 (17)	0.0108 (16)	0.0142 (15)
C5	0.087 (3)	0.060 (2)	0.048 (2)	0.037 (2)	0.0177 (18)	0.0259 (17)
C6	0.078 (3)	0.057 (2)	0.057 (2)	0.030 (2)	0.0191 (19)	0.0255 (18)
C7	0.072 (2)	0.049 (2)	0.067 (2)	0.0285 (18)	0.0145 (19)	0.0180 (17)
C8	0.073 (2)	0.062 (2)	0.049 (2)	0.0373 (19)	0.0100 (17)	0.0149 (17)
C9	0.073 (2)	0.0505 (19)	0.0439 (18)	0.0305 (18)	0.0133 (16)	0.0173 (15)
C10	0.096 (3)	0.076 (3)	0.056 (2)	0.026 (2)	0.006 (2)	0.012 (2)
O3	0.0994 (19)	0.0705 (16)	0.0524 (15)	0.0462 (15)	0.0200 (13)	0.0246 (12)
O4	0.140 (3)	0.0684 (17)	0.0626 (17)	0.0603 (18)	0.0224 (16)	0.0110 (14)
N2	0.148 (3)	0.070 (2)	0.0511 (18)	0.065 (2)	0.0102 (19)	0.0136 (16)
C11	0.135 (4)	0.104 (4)	0.066 (3)	0.053 (3)	0.022 (3)	0.038 (3)
C12	0.102 (3)	0.068 (2)	0.066 (3)	0.041 (2)	0.012 (2)	0.027 (2)
C13	0.077 (2)	0.064 (2)	0.047 (2)	0.034 (2)	0.0102 (17)	0.0113 (17)
C14	0.072 (2)	0.055 (2)	0.0380 (17)	0.0288 (17)	0.0062 (15)	0.0088 (15)
C15	0.079 (2)	0.056 (2)	0.0427 (18)	0.0406 (18)	0.0107 (16)	0.0082 (15)
C16	0.076 (2)	0.061 (2)	0.0390 (17)	0.0380 (18)	0.0113 (16)	0.0099 (15)
C17	0.094 (3)	0.055 (2)	0.0438 (19)	0.045 (2)	0.0064 (17)	0.0099 (15)
C18	0.117 (3)	0.064 (2)	0.0439 (19)	0.057 (2)	0.011 (2)	0.0021 (17)
C19	0.099 (3)	0.069 (2)	0.0382 (18)	0.041 (2)	0.0134 (18)	0.0084 (17)
C20	0.120 (3)	0.095 (3)	0.042 (2)	0.068 (3)	0.022 (2)	0.0199 (19)

O1—C3	1.351 (4)	O3—C13	1.362 (4)
O1—C2	1.446 (4)	O3—C12	1.452 (4)
O2—C3	1.232 (4)	O4—C13	1.207 (4)
N1—C7	1.369 (5)	N2—C17	1.365 (4)
N1—H1A	0.8600	N2—H2C	0.8600
N1—H1B	0.8600	N2—H2D	0.8600
C1—C2	1.503 (5)	C11—C12	1.513 (5)
C1—H1C	0.9600	C11—H11A	0.9600
C1—H1D	0.9600	C11—H11B	0.9600
C1—H1E	0.9600	C11—H11C	0.9600
C2—H2A	0.9700	C12—H12A	0.9700
C2—H2B	0.9700	C12—H12B	0.9700
C3—C4	1.432 (5)	C13—C14	1.458 (5)
C4—C5	1.407 (4)	C14—C19	1.374 (5)
C4—C9	1.409 (4)	C14—C15	1.411 (4)
C5—C6	1.349 (5)	C15—C16	1.375 (4)
C5—H5A	0.9300	C15—H15A	0.9300
C6—C7	1.404 (5)	C16—C17	1.409 (4)
C6—H6A	0.9300	C16—C20	1.522 (4)
C7—C8	1.414 (5)	C17—C18	1.409 (4)
C8—C9	1.367 (5)	C18—C19	1.376 (5)
C8—C10	1.509 (5)	C18—H18A	0.9300
C9—H9A	0.9300	C19—H19A	0.9300
C10—H10A	0.9600	C20—H20A	0.9600
C10—H10B	0.9600	C20—H20B	0.9600
C10—H10C	0.9600	C20—H20C	0.9600
C3—O1—C2	118.2 (3)	C13—O3—C12	116.0 (3)
C7—N1—H1A	120.0	C17—N2—H2C	120.0
C7—N1—H1B	120.0	C17—N2—H2D	120.0
H1A—N1—H1B	120.0	H2C—N2—H2D	120.0
C2—C1—H1C	109.5	C12—C11—H11A	109.5
C2—C1—H1D	109.5	C12—C11—H11B	109.5
H1C—C1—H1D	109.5	H11A—C11—H11B	109.5
C2—C1—H1E	109.5	C12—C11—H11C	109.5
H1C—C1—H1E	109.5	H11A—C11—H11C	109.5
H1D—C1—H1E	109.5	H11B—C11—H11C	109.5
O1—C2—C1	107.6 (3)	O3—C12—C11	106.2 (3)
O1—C2—H2A	110.2	O3—C12—H12A	110.5
C1—C2—H2A	110.2	C11—C12—H12A	110.5
O1—C2—H2B	110.2	O3—C12—H12B	110.5
C1—C2—H2B	110.2	C11—C12—H12B	110.5
H2A—C2—H2B	108.5	H12A—C12—H12B	108.7
O2—C3—O1	120.3 (3)	O4—C13—O3	121.9 (3)
O2—C3—C4	126.2 (3)	O4—C13—C14	125.8 (3)
O1—C3—C4	113.5 (3)	O3—C13—C14	112.2 (3)
C5—C4—C9	116.4 (3)	C19—C14—C15	118.2 (3)
C5—C4—C3	123.1 (3)	C19—C14—C13	123.8 (3)
C9—C4—C3	120.5 (3)	C15—C14—C13	118.0 (3)
C6—C5—C4	121.0 (3)	C16—C15—C14	122.3 (3)
C6—C5—H5A	119.5	C16—C15—H15A	118.8
C4—C5—H5A	119.5	C14—C15—H15A	118.8
C5—C6—C7	121.8 (3)	C15—C16—C17	118.7 (3)
C5—C6—H6A	119.1	C15—C16—C20	120.9 (3)
C7—C6—H6A	119.1	C17—C16—C20	120.4 (3)
N1—C7—C6	121.1 (3)	N2—C17—C16	121.3 (3)
N1—C7—C8	119.7 (3)	N2—C17—C18	119.7 (3)
C6—C7—C8	119.1 (3)	C16—C17—C18	119.0 (3)
C9—C8—C7	117.5 (3)	C19—C18—C17	120.8 (3)
C9—C8—C10	121.9 (3)	C19—C18—H18A	119.6
C7—C8—C10	120.6 (3)	C17—C18—H18A	119.6
C8—C9—C4	124.2 (3)	C14—C19—C18	121.0 (3)
C8—C9—H9A	117.9	C14—C19—H19A	119.5
C4—C9—H9A	117.9	C18—C19—H19A	119.5
C8—C10—H10A	109.5	C16—C20—H20A	109.5
C8—C10—H10B	109.5	C16—C20—H20B	109.5
H10A—C10—H10B	109.5	H20A—C20—H20B	109.5
C8—C10—H10C	109.5	C16—C20—H20C	109.5
H10A—C10—H10C	109.5	H20A—C20—H20C	109.5
H10B—C10—H10C	109.5	H20B—C20—H20C	109.5
C3—O1—C2—C1	178.1 (3)	C13—O3—C12—C11	−177.7 (3)
C2—O1—C3—O2	1.4 (5)	C12—O3—C13—O4	−2.5 (5)
C2—O1—C3—C4	179.7 (3)	C12—O3—C13—C14	−179.4 (3)
O2—C3—C4—C5	−176.4 (3)	O4—C13—C14—C19	176.4 (4)
O1—C3—C4—C5	5.4 (5)	O3—C13—C14—C19	−6.9 (5)
O2—C3—C4—C9	2.0 (5)	O4—C13—C14—C15	−0.8 (6)
O1—C3—C4—C9	−176.2 (3)	O3—C13—C14—C15	176.0 (3)
C9—C4—C5—C6	1.4 (5)	C19—C14—C15—C16	0.8 (5)
C3—C4—C5—C6	179.9 (3)	C13—C14—C15—C16	178.1 (3)
C4—C5—C6—C7	−1.9 (6)	C14—C15—C16—C17	−1.4 (5)
C5—C6—C7—N1	179.2 (4)	C14—C15—C16—C20	−179.6 (3)
C5—C6—C7—C8	2.7 (6)	C15—C16—C17—N2	179.5 (4)
N1—C7—C8—C9	−179.6 (3)	C20—C16—C17—N2	−2.3 (6)
C6—C7—C8—C9	−3.0 (5)	C15—C16—C17—C18	1.3 (5)
N1—C7—C8—C10	2.9 (5)	C20—C16—C17—C18	179.5 (4)
C6—C7—C8—C10	179.4 (3)	N2—C17—C18—C19	−178.9 (4)
C7—C8—C9—C4	2.8 (5)	C16—C17—C18—C19	−0.7 (6)
C10—C8—C9—C4	−179.7 (3)	C15—C14—C19—C18	−0.1 (6)
C5—C4—C9—C8	−2.0 (5)	C13—C14—C19—C18	−177.2 (4)
C3—C4—C9—C8	179.6 (3)	C17—C18—C19—C14	0.0 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.86	2.33	3.023 (5)	138
N1—H1B···N2	0.86	2.61	3.242 (5)	131
N2—H2C···O2i	0.86	2.35	3.160 (4)	157
N2—H2D···O4ii	0.86	2.15	2.967 (4)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.86	2.33	3.023 (5)	138
N1—H1B⋯N2	0.86	2.61	3.242 (5)	131
N2—H2C⋯O2i	0.86	2.35	3.160 (4)	157
N2—H2D⋯O4ii	0.86	2.15	2.967 (4)	158

Symmetry codes: (i) ; (ii) .