Ethyl 4-amino-3-methyl­benzoate

Song, W.-L.; Wang, D.; Li, X.-H.; Wang, D.-C.

doi:10.1107/S1600536808005989

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o785

doi:10.1107/S1600536808005989

Open

access

Ethyl 4-amino-3-methylbenzoate

Wen-Lan Song,^a Dan Wang,^b Xin-Hua Li ^a and De-Cai Wang ^a ^*

^aDepartment of Pharmaceutical Engineering, College of Life Sciences and Pharmaceutical Engineering, Nanjing University of Technolgy, Xinmofan Road No. 5, Nanjing 210009, People's Republic of China, and ^bBioengineering Department, Xuzhou Higher Vocational College of Bioengineering, Mine West Road, Xuzhou, Xuzhou 221006, People's Republic of China
^*Correspondence e-mail: dcwang@njut.edu.cn

(Received 27 February 2008; accepted 4 March 2008; online 2 April 2008)

The asymmetric unit of the title compound, C₁₀H₁₃NO₂, contains two molecules which are linked via an N—H⋯N hydrogen bonds to form a dimer. These dimers are further linked via N—H⋯O intermolecular 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_r = 179.21
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.074
wR(F²) = 0.176
S = 1.02
3594 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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) x-1, y-1, z; (ii) x, y-1, z.

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

Supporting information

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

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

checkCIF report

Comment top

Ethyl 3-methyl-4-aminobenzoate is a material for preparing the important intermidates of bis-(2-haloethyl)aminophenyl substituted distamycin derivatives(Baraldi et al., 2007), which are used as antitumor alkylating and antiviral agents related to the known antibiotic distamycin A (Baraldi et al., 1999). Distamycin A belongs to the family of the pyrroleamidine antibiotics (Baraldi et al., 2000) and is reported to interact reversibly and selectively with DNA-AT sequences interfering with both replication and transcription (Baraldi et al., 2003). Bis-(2-haloethyl)aminophenyl substituted distamycin derivatives can therefore be used in a treatment to ameliorate a cancer (Wang et al., 2003). They may be administered to improve the condition of a patient having a leukaemia lymphoma, sarcoma, such as myeloblastic leukaemia, neuroblastoma, Wilm's tumor or malignant neoplasm of the bladder, breast, lung or thyroid. (Zaffaroni et al., 2002).

The molecular structure of (I) is shown in Fig. 1. The bond lengths and angles are within normal ranges (Allen et al., 1987).

The asymmetric unit of the title compound, contains two molecules which are linked via N—H···N hydrogen bonds to form dimers. In the crystals, molecules are linked via N—H···O Intermolecular hydrogen bonds (Table 1), which may be effective in the stabilization of the crystals.

Related literature top

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 top

The title compound was prepared from 3-Methyl-4-aminobenzoic acid (15.2 g, 100 mmole) in ethanol (40.4 ml, 1000 mmole). After the solid has melted, concentrated hydrochloric acid (142 g, 120 ml) was added dropwise from a dropping funnel at 90°C, the the reaction mixture was cooled with ice and water and finaly the product was filtered by suction. Suitable crystals were obtained by evaporation of a methanol solution for about 3 d.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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 (Sheldrick, 2008).

Figures top

Fig. 1. A view of the molecular structure of (I), showing displacement ellipsoids at the 50% probability level. N—H···N hydrogen bonds are shown as dashed lines.

Ethyl 4-amino-3-methylbenzoate top

Crystal data top

C₁₀H₁₃NO₂	Z = 4
M_r = 179.21	F(000) = 384
Triclinic, P1	D_x = 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 = 10–14°
c = 15.835 (3) Å	µ = 0.08 mm⁻¹
α = 90.78 (3)°	T = 298 K
β = 95.13 (3)°	Block, colorless
γ = 114.34 (3)°	0.30 × 0.20 × 0.10 mm
V = 1000.3 (3) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	2146 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.052
Graphite monochromator	θ_max = 25.2°, θ_min = 1.3°
ω/2θ scans	h = −9→9
Absorption correction: ψ scan (North et al., 1968)	k = −10→10
T_min = 0.975, T_max = 0.991	l = 0→18
3874 measured reflections	3 standard reflections every 200 reflections
3594 independent reflections	intensity decay: none

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.177	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.04P)² + 1.2P] where P = (F_o² + 2F_c²)/3
3594 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₀H₁₃NO₂	γ = 114.34 (3)°
M_r = 179.21	V = 1000.3 (3) Å³
Triclinic, P1	Z = 4
a = 8.0110 (16) Å	Mo Kα radiation
b = 8.7030 (17) Å	µ = 0.08 mm⁻¹
c = 15.835 (3) Å	T = 298 K
α = 90.78 (3)°	0.30 × 0.20 × 0.10 mm
β = 95.13 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2146 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.052
T_min = 0.975, T_max = 0.991	3 standard reflections every 200 reflections
3874 measured reflections	intensity decay: none
3594 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	0 restraints
wR(F²) = 0.177	H-atom parameters constrained
S = 1.02	Δρ_max = 0.23 e Å⁻³
3594 reflections	Δρ_min = −0.23 e Å⁻³
235 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	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1, y−1, z; (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₃NO₂
M_r	179.21
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.0110 (16), 8.7030 (17), 15.835 (3)
α, β, γ (°)	90.78 (3), 95.13 (3), 114.34 (3)
V (Å³)	1000.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
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	0.975, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	3874, 3594, 2146
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.598

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.177, 1.02
No. of reflections	3594
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.23

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4(Harms & Wocadlo,1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x−1, y−1, z; (ii) x, y−1, z.

Acknowledgements

The authors thank Dr Shan Liu for useful discussions.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Baraldi, P. G., Beria, I., Cozzi, P., Bianchi, N., Gambari, R. & Romagnoli, R. (2003). Bioorg. Med. Chem. 11, 965–975. Web of Science CrossRef PubMed CAS Google Scholar
Baraldi, P. G., Cozzi, P., Geroni, C., Mongelli, N., Romagnoli, R. & Spallu, G. (1999). Bioorg. Med. Chem. 7, 251–262. Web of Science CrossRef PubMed CAS Google Scholar
Baraldi, P. G., Preti, D., Fruttarolo, F., Tabrizi, M. A. & Romagnoli, R. (2007). Bioorg. Med. Chem. 15, 17–35. Web of Science CrossRef PubMed CAS Google Scholar
Baraldi, P. G., Romagnoli, R., Duatti, A., Bolzati, C., Piffanelli, A., Bianchi, N., Mischiati, C. & Gambari, R. (2000). Bioorg. Med. Chem. Lett. 10, 1397–1400. Web of Science CrossRef PubMed CAS Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Y. Q., Wright, S. C. & Larrick, J. W. (2003). Bioorg. Med. Chem. Lett. 13, 459–461. Web of Science CrossRef PubMed CAS Google Scholar
Zaffaroni, N., Luald, S., Villa, R., Bellarosa, D., Cermele, C., Felicetti, P., Rossi, C., Orlandi, L. & Daidone, M. G. (2002). Eur. J. Cancer, 38, 1792–1801. Web of Science CrossRef PubMed CAS Google Scholar