Ethyl 2-(3-amino-4-hy-droxy-phen-yl)acetate.

The asymmetric unit of the title compound, C(10)H(13)NO(3), contains two crystallographically independent mol-ecules with different conformations of the eth-oxy-carbonyl groups; the terminal C-C-O-C torsion angles in the two mol-ecules are 83.6 (6) and -171.1 (3)°, resulting in twisted and straight chain conformations, respectively. The crystal structure is stabilized by inter-molecular N-H⋯O, O-H⋯N and C-H⋯O hydrogen bonds. Intra-molecular hydrogen bonds occur between the amino N and phenolic O atoms.

Related literature

For general background to the use of phenyl­acetate derivatives as inter­mediates for the rational design of new chemotherapeutic agents, see: Xiao, Fang et al. (2008 ▶); Xiao, Lv et al. (2008 ▶). For the preparation of the title compound, see: Xiao et al. 2010 ▶. For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H13NO3

M = 195.21

Triclinic,

a = 8.5940 (17) Å

b = 10.142 (2) Å

c = 12.043 (2) Å

α = 98.23 (3)°

β = 104.96 (3)°

γ = 90.41 (3)°

V = 1002.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.30 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.972, T max = 0.991

3857 measured reflections

3598 independent reflections

2121 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.079

wR(F 2) = 0.213

S = 1.09

3598 reflections

247 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 global, I. DOI: 10.1107/S1600536810044399/pv2339sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044399/pv2339Isup2.hkl

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

C10H13NO3	Z = 4
Mr = 195.21	F(000) = 416
Triclinic, P1	Dx = 1.293 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5940 (17) Å	Cell parameters from 2097 reflections
b = 10.142 (2) Å	θ = 2.4–24.9°
c = 12.043 (2) Å	µ = 0.10 mm−1
α = 98.23 (3)°	T = 293 K
β = 104.96 (3)°	Block, colorless
γ = 90.41 (3)°	0.30 × 0.10 × 0.10 mm
V = 1002.6 (3) Å3

Bruker SMART APEX CCD diffractometer	3598 independent reflections
Radiation source: fine-focus sealed tube	2121 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 25.2°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
Tmin = 0.972, Tmax = 0.991	k = −12→12
3857 measured reflections	l = 0→14

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)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.213	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0847P)2 + 0.7608P] where P = (Fo2 + 2Fc2)/3
3598 reflections	(Δ/σ)max < 0.001
247 parameters	Δρmax = 0.32 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	1.0536 (4)	0.8579 (3)	0.9060 (3)	0.0860 (11)
O2	1.2035 (3)	0.7342 (3)	0.8128 (3)	0.0690 (9)
O3	0.9659 (3)	0.2198 (3)	0.4667 (3)	0.0611 (8)
H3A	1.0353	0.1671	0.4878	0.092*
N1	0.7667 (5)	0.3994 (3)	0.4283 (3)	0.063
H1A	0.6993	0.4586	0.4059	0.075*
H1B	0.7774	0.3314	0.3797	0.075*
C1	1.1307 (7)	1.0449 (5)	0.8320 (6)	0.102 (2)
H1C	1.2096	1.1172	0.8466	0.153*
H1D	1.0260	1.0801	0.8263	0.153*
H1E	1.1306	0.9893	0.7604	0.153*
C2	1.1679 (6)	0.9708 (5)	0.9218 (5)	0.0779 (15)
H2A	1.1697	1.0281	0.9939	0.093*
H2B	1.2750	0.9377	0.9283	0.093*
C3	1.0796 (5)	0.7484 (4)	0.8404 (4)	0.0513 (10)
C4	0.9484 (5)	0.6448 (4)	0.8233 (4)	0.0655 (13)
H4A	0.8454	0.6861	0.8036	0.079*
H4B	0.9581	0.6112	0.8962	0.079*
C5	0.9492 (5)	0.5276 (4)	0.7290 (4)	0.0500 (10)
C6	1.0634 (5)	0.4308 (4)	0.7533 (4)	0.0514 (10)
H6A	1.1342	0.4357	0.8267	0.062*
C7	1.0690 (5)	0.3282 (4)	0.6664 (4)	0.0531 (10)
H7A	1.1455	0.2644	0.6825	0.064*
C8	0.9663 (4)	0.3164 (3)	0.5569 (3)	0.0430 (9)
C9	0.8494 (4)	0.4121 (3)	0.5322 (3)	0.0424 (9)
C10	0.8459 (5)	0.5164 (4)	0.6213 (4)	0.0498 (10)
H10A	0.7697	0.5806	0.6061	0.060*
O4	0.3631 (3)	0.5329 (2)	0.1330 (2)	0.0541 (7)
O5	0.5351 (4)	0.6553 (3)	0.2847 (3)	0.0739 (10)
O6	0.4558 (4)	1.2663 (3)	0.4366 (3)	0.0727 (10)
H6B	0.5107	1.3115	0.4082	0.087*
N2	0.2886 (4)	1.1022 (4)	0.5184 (3)	0.0628 (10)
H2C	0.2324	1.0498	0.5447	0.075*
H2D	0.3165	1.1816	0.5548	0.075*
C11	0.4060 (6)	0.3167 (4)	0.0431 (4)	0.0734 (14)
H11A	0.4722	0.2412	0.0527	0.110*
H11B	0.4119	0.3505	−0.0263	0.110*
H11C	0.2963	0.2901	0.0369	0.110*
C12	0.4636 (5)	0.4217 (4)	0.1442 (4)	0.0642 (12)
H12A	0.4625	0.3866	0.2148	0.077*
H12B	0.5737	0.4501	0.1496	0.077*
C13	0.4116 (5)	0.6431 (4)	0.2094 (3)	0.0465 (9)
C14	0.2909 (5)	0.7474 (4)	0.1919 (4)	0.0570 (11)
H14A	0.1973	0.7178	0.2141	0.068*
H14B	0.2568	0.7527	0.1094	0.068*
C15	0.3408 (4)	0.8849 (3)	0.2550 (3)	0.0454 (9)
C16	0.4443 (5)	0.9678 (4)	0.2213 (4)	0.0559 (11)
H16A	0.4852	0.9373	0.1584	0.067*
C17	0.4866 (5)	1.0952 (4)	0.2809 (3)	0.0508 (10)
H17A	0.5512	1.1512	0.2548	0.061*
C18	0.4349 (4)	1.1409 (3)	0.3781 (3)	0.0374 (8)
C19	0.3347 (4)	1.0583 (3)	0.4161 (3)	0.0403 (8)
C20	0.2923 (4)	0.9312 (3)	0.3547 (3)	0.0443 (9)
H20A	0.2290	0.8746	0.3812	0.053*

	U11	U22	U33	U12	U13	U23
O1	0.090 (2)	0.0554 (19)	0.127 (3)	−0.0022 (17)	0.072 (2)	−0.0197 (19)
O2	0.0548 (18)	0.0541 (18)	0.104 (2)	0.0050 (14)	0.0410 (17)	−0.0067 (16)
O3	0.0565 (17)	0.0441 (16)	0.092 (2)	0.0117 (13)	0.0403 (15)	0.0021 (15)
N1	0.082	0.039	0.083	−0.002	0.049	0.011
C1	0.092 (4)	0.067 (3)	0.132 (5)	−0.005 (3)	−0.001 (4)	0.023 (4)
C2	0.080 (3)	0.054 (3)	0.099 (4)	−0.001 (3)	0.036 (3)	−0.014 (3)
C3	0.051 (2)	0.045 (2)	0.063 (3)	0.0007 (18)	0.030 (2)	−0.0049 (19)
C4	0.057 (3)	0.056 (3)	0.093 (3)	0.000 (2)	0.048 (2)	−0.011 (2)
C5	0.050 (2)	0.042 (2)	0.072 (3)	0.0019 (18)	0.044 (2)	0.0027 (19)
C6	0.042 (2)	0.056 (3)	0.060 (2)	0.0005 (18)	0.0209 (18)	0.008 (2)
C7	0.042 (2)	0.051 (2)	0.077 (3)	0.0067 (17)	0.032 (2)	0.015 (2)
C8	0.045 (2)	0.0288 (18)	0.064 (3)	−0.0039 (15)	0.0325 (19)	0.0027 (17)
C9	0.043 (2)	0.039 (2)	0.054 (2)	−0.0008 (16)	0.0248 (17)	0.0128 (17)
C10	0.052 (2)	0.035 (2)	0.077 (3)	0.0142 (17)	0.042 (2)	0.0121 (19)
O4	0.0550 (16)	0.0347 (14)	0.0755 (19)	0.0100 (12)	0.0259 (14)	0.0012 (13)
O5	0.0589 (19)	0.0487 (17)	0.099 (2)	0.0180 (14)	0.0063 (18)	−0.0132 (16)
O6	0.103 (2)	0.0329 (15)	0.098 (2)	−0.0021 (15)	0.063 (2)	−0.0031 (15)
N2	0.072 (2)	0.054 (2)	0.080 (3)	0.0021 (17)	0.052 (2)	0.0063 (18)
C11	0.086 (3)	0.048 (3)	0.103 (4)	0.012 (2)	0.064 (3)	−0.007 (2)
C12	0.061 (3)	0.049 (2)	0.090 (3)	0.020 (2)	0.031 (2)	0.012 (2)
C13	0.049 (2)	0.036 (2)	0.058 (2)	−0.0049 (17)	0.0269 (19)	−0.0070 (17)
C14	0.046 (2)	0.044 (2)	0.077 (3)	−0.0004 (18)	0.016 (2)	−0.006 (2)
C15	0.042 (2)	0.0305 (19)	0.068 (3)	0.0096 (15)	0.0244 (18)	0.0029 (17)
C16	0.054 (2)	0.052 (2)	0.077 (3)	0.0091 (19)	0.042 (2)	0.010 (2)
C17	0.059 (2)	0.040 (2)	0.065 (3)	0.0037 (18)	0.034 (2)	0.0120 (19)
C18	0.0343 (18)	0.0245 (17)	0.053 (2)	0.0034 (13)	0.0115 (15)	0.0042 (15)
C19	0.0350 (18)	0.038 (2)	0.055 (2)	0.0165 (15)	0.0225 (16)	0.0106 (17)
C20	0.044 (2)	0.0311 (19)	0.060 (2)	−0.0016 (15)	0.0172 (18)	0.0090 (17)

O1—C3	1.324 (5)	O4—C13	1.331 (4)
O1—C2	1.462 (6)	O4—C12	1.426 (5)
O2—C3	1.199 (4)	O5—C13	1.198 (5)
O3—C8	1.353 (4)	O6—C18	1.350 (4)
O3—H3A	0.8200	O6—H6B	0.8200
N1—C9	1.257 (5)	N2—C19	1.405 (5)
N1—H1A	0.8600	N2—H2C	0.8600
N1—H1B	0.8600	N2—H2D	0.8600
C1—C2	1.376 (7)	C11—C12	1.474 (6)
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	1.489 (5)	C13—C14	1.485 (6)
C4—C5	1.523 (5)	C14—C15	1.491 (5)
C4—H4A	0.9700	C14—H14A	0.9700
C4—H4B	0.9700	C14—H14B	0.9700
C5—C10	1.359 (6)	C15—C20	1.391 (5)
C5—C6	1.400 (6)	C15—C16	1.391 (5)
C6—C7	1.377 (5)	C16—C17	1.382 (5)
C6—H6A	0.9300	C16—H16A	0.9300
C7—C8	1.372 (6)	C17—C18	1.379 (5)
C7—H7A	0.9300	C17—H17A	0.9300
C8—C9	1.408 (5)	C18—C19	1.398 (5)
C9—C10	1.401 (5)	C19—C20	1.386 (5)
C10—H10A	0.9300	C20—H20A	0.9300
C3—O1—C2	116.0 (3)	C13—O4—C12	117.4 (3)
C8—O3—H3A	109.5	C18—O6—H6B	109.5
C9—N1—H1A	120.0	C19—N2—H2C	120.0
C9—N1—H1B	120.0	C19—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
C1—C2—O1	113.0 (5)	O4—C12—C11	110.2 (4)
C1—C2—H2A	109.0	O4—C12—H12A	109.6
O1—C2—H2A	109.0	C11—C12—H12A	109.6
C1—C2—H2B	109.0	O4—C12—H12B	109.6
O1—C2—H2B	109.0	C11—C12—H12B	109.6
H2A—C2—H2B	107.8	H12A—C12—H12B	108.1
O2—C3—O1	121.8 (4)	O5—C13—O4	124.2 (4)
O2—C3—C4	126.7 (4)	O5—C13—C14	124.3 (3)
O1—C3—C4	110.9 (3)	O4—C13—C14	111.5 (3)
C3—C4—C5	114.2 (3)	C13—C14—C15	117.7 (3)
C3—C4—H4A	108.7	C13—C14—H14A	107.9
C5—C4—H4A	108.7	C15—C14—H14A	107.9
C3—C4—H4B	108.7	C13—C14—H14B	107.9
C5—C4—H4B	108.7	C15—C14—H14B	107.9
H4A—C4—H4B	107.6	H14A—C14—H14B	107.2
C10—C5—C6	119.1 (4)	C20—C15—C16	117.7 (3)
C10—C5—C4	122.0 (4)	C20—C15—C14	120.4 (3)
C6—C5—C4	118.8 (4)	C16—C15—C14	121.8 (4)
C7—C6—C5	118.8 (4)	C17—C16—C15	120.3 (4)
C7—C6—H6A	120.6	C17—C16—H16A	119.8
C5—C6—H6A	120.6	C15—C16—H16A	119.8
C8—C7—C6	122.6 (4)	C18—C17—C16	121.2 (4)
C8—C7—H7A	118.7	C18—C17—H17A	119.4
C6—C7—H7A	118.7	C16—C17—H17A	119.4
O3—C8—C7	126.1 (4)	O6—C18—C17	126.4 (3)
O3—C8—C9	114.9 (4)	O6—C18—C19	113.6 (3)
C7—C8—C9	119.0 (3)	C17—C18—C19	119.6 (3)
N1—C9—C10	126.8 (4)	C20—C19—C18	118.4 (3)
N1—C9—C8	115.3 (4)	C20—C19—N2	121.9 (3)
C10—C9—C8	117.7 (4)	C18—C19—N2	119.6 (3)
C5—C10—C9	122.7 (4)	C19—C20—C15	122.6 (3)
C5—C10—H10A	118.6	C19—C20—H20A	118.7
C9—C10—H10A	118.6	C15—C20—H20A	118.7
C3—O1—C2—C1	83.7 (6)	C13—O4—C12—C11	−171.1 (3)
C2—O1—C3—O2	12.7 (7)	C12—O4—C13—O5	1.6 (6)
C2—O1—C3—C4	−175.5 (4)	C12—O4—C13—C14	−176.5 (3)
O2—C3—C4—C5	−21.0 (7)	O5—C13—C14—C15	13.4 (6)
O1—C3—C4—C5	167.7 (4)	O4—C13—C14—C15	−168.5 (3)
C3—C4—C5—C10	−101.7 (5)	C13—C14—C15—C20	−102.0 (5)
C3—C4—C5—C6	76.3 (5)	C13—C14—C15—C16	74.0 (5)
C10—C5—C6—C7	1.0 (5)	C20—C15—C16—C17	−4.7 (6)
C4—C5—C6—C7	−177.0 (3)	C14—C15—C16—C17	179.2 (4)
C5—C6—C7—C8	−0.5 (6)	C15—C16—C17—C18	3.5 (6)
C6—C7—C8—O3	179.0 (3)	C16—C17—C18—O6	−173.4 (4)
C6—C7—C8—C9	−0.5 (5)	C16—C17—C18—C19	−1.5 (6)
O3—C8—C9—N1	−3.8 (4)	O6—C18—C19—C20	173.8 (3)
C7—C8—C9—N1	175.7 (3)	C17—C18—C19—C20	0.9 (5)
O3—C8—C9—C10	−178.7 (3)	O6—C18—C19—N2	−10.3 (5)
C7—C8—C9—C10	0.8 (5)	C17—C18—C19—N2	176.8 (3)
C6—C5—C10—C9	−0.6 (5)	C18—C19—C20—C15	−2.4 (5)
C4—C5—C10—C9	177.3 (3)	N2—C19—C20—C15	−178.2 (4)
N1—C9—C10—C5	−174.5 (4)	C16—C15—C20—C19	4.2 (6)
C8—C9—C10—C5	−0.3 (5)	C14—C15—C20—C19	−179.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2i	0.86	2.37	3.097 (5)	143
N2—H2D···O5ii	0.86	2.42	3.222 (5)	155
O3—H3A···N2iii	0.82	2.23	2.978 (5)	152
O6—H6B···N1iv	0.82	2.31	3.015 (5)	145
C10—H10A···O6ii	0.93	2.49	3.414 (5)	174
N1—H1B···O3	0.86	2.12	2.517 (5)	108
N2—H2D···O6	0.86	2.33	2.641 (4)	102

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O2i	0.86	2.37	3.097 (5)	143
N2—H2D⋯O5ii	0.86	2.42	3.222 (5)	155
O3—H3A⋯N2iii	0.82	2.23	2.978 (5)	152
O6—H6B⋯N1iv	0.82	2.31	3.015 (5)	145
C10—H10A⋯O6ii	0.93	2.49	3.414 (5)	174
N1—H1B⋯O3	0.86	2.12	2.517 (5)	108
N2—H2D⋯O6	0.86	2.33	2.641 (4)	102

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .