(S)-Benzyl 2-amino-3-(4-hydroxy-phen-yl)propanoate.

The title compound, C(16)H(17)NO(3), adopts a folded conformation in the crystal structure. The crystal packing is stabilized by inter-molecular O-H⋯O and N-H⋯O hydrogen-bonding inter-actions. The absolute configuration was assigned assuming that the absolute configuration of the starting material l-tyrosine was retained during the synthesis.

Related literature

For background, see: Nakamura et al. (1998 ▶). For the n-butyl analogue, see: Qian et al. (2006 ▶).

Experimental

Crystal data

C16H17NO3

M = 271.31

Orthorhombic,

a = 5.1589 (2) Å

b = 15.1430 (4) Å

c = 18.6367 (6) Å

V = 1455.92 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.25 × 0.22 × 0.18 mm

Data collection

Bruker SMART APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.979, T max = 0.985

8138 measured reflections

1672 independent reflections

1172 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.076

S = 0.93

1672 reflections

193 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.08 e Å−3

Δρmin = −0.10 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808044218/wk2093sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808044218/wk2093Isup2.hkl

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

C16H17NO3	F(000) = 576
Mr = 271.31	Dx = 1.238 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2651 reflections
a = 5.1589 (2) Å	θ = 2.7–32.7°
b = 15.1430 (4) Å	µ = 0.09 mm−1
c = 18.6367 (6) Å	T = 293 K
V = 1455.92 (8) Å3	Plate, colorless
Z = 4	0.25 × 0.22 × 0.18 mm

Bruker APEX area-detector diffractometer	1672 independent reflections
Radiation source: fine-focus sealed tube	1172 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 26.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −5→6
Tmin = 0.979, Tmax = 0.985	k = −18→16
8138 measured reflections	l = −22→22

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)] = 0.032	Hydrogen site location: geom CH, N and OH from difmap
wR(F2) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ2(Fo2) + (0.0454P)2] where P = (Fo2 + 2Fc2)/3
1672 reflections	(Δ/σ)max < 0.001
193 parameters	Δρmax = 0.08 e Å−3
0 restraints	Δρmin = −0.10 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	0.4947 (3)	0.30756 (10)	0.45476 (9)	0.0650 (5)
O2	0.8528 (3)	0.38687 (8)	0.43244 (8)	0.0538 (4)
O3	0.7826 (4)	0.60066 (9)	0.17256 (9)	0.0648 (5)
N1	0.7847 (5)	0.15910 (11)	0.39585 (11)	0.0499 (5)
C1	0.7006 (4)	0.31643 (12)	0.42536 (11)	0.0451 (5)
C2	0.8176 (4)	0.25132 (12)	0.37341 (10)	0.0441 (5)
H2A	1.0032	0.2638	0.3688	0.053*
C3	0.6894 (5)	0.26200 (12)	0.29951 (11)	0.0564 (6)
H3B	0.7642	0.2188	0.2672	0.068*
H3C	0.5065	0.2484	0.3042	0.068*
C4	0.7151 (5)	0.35192 (13)	0.26566 (11)	0.0491 (5)
C5	0.9175 (5)	0.37134 (14)	0.21981 (12)	0.0598 (6)
H5A	1.0392	0.3278	0.2096	0.072*
C6	0.9440 (5)	0.45339 (13)	0.18877 (12)	0.0558 (6)
H6A	1.0822	0.4644	0.1580	0.067*
C7	0.7680 (4)	0.51880 (12)	0.20290 (11)	0.0470 (5)
C8	0.5653 (5)	0.50079 (14)	0.24802 (13)	0.0591 (6)
H8A	0.4431	0.5443	0.2578	0.071*
C9	0.5413 (5)	0.41866 (15)	0.27908 (12)	0.0593 (6)
H9A	0.4034	0.4081	0.3100	0.071*
C10	0.7522 (5)	0.45997 (13)	0.47444 (13)	0.0634 (6)
H10A	0.7322	0.4426	0.5242	0.076*
H10B	0.5845	0.4782	0.4562	0.076*
C11	0.9434 (5)	0.53384 (13)	0.46821 (13)	0.0531 (6)
C12	1.0032 (7)	0.56917 (19)	0.40256 (15)	0.0943 (10)
H12A	0.9254	0.5469	0.3613	0.113*
C13	1.1791 (9)	0.6379 (2)	0.39742 (18)	0.1095 (12)
H13A	1.2166	0.6621	0.3527	0.131*
C14	1.2967 (7)	0.67010 (17)	0.4564 (2)	0.0909 (9)
H14A	1.4155	0.7161	0.4526	0.109*
C15	1.2409 (7)	0.63529 (17)	0.52081 (19)	0.0889 (9)
H15A	1.3218	0.6573	0.5617	0.107*
C16	1.0650 (6)	0.56733 (15)	0.52689 (14)	0.0687 (7)
H16A	1.0287	0.5439	0.5719	0.082*
H1A	0.816 (5)	0.1545 (14)	0.4419 (14)	0.060 (7)*
H1B	0.613 (7)	0.1410 (17)	0.3878 (16)	0.091 (9)*
H3	0.941 (6)	0.6089 (16)	0.1494 (15)	0.094 (10)*

	U11	U22	U33	U12	U13	U23
O1	0.0604 (10)	0.0618 (9)	0.0728 (11)	−0.0057 (8)	0.0199 (9)	−0.0112 (8)
O2	0.0563 (8)	0.0399 (7)	0.0652 (9)	−0.0023 (7)	0.0044 (8)	−0.0138 (7)
O3	0.0676 (11)	0.0502 (8)	0.0766 (11)	0.0065 (8)	0.0092 (10)	0.0187 (8)
N1	0.0652 (13)	0.0378 (9)	0.0467 (11)	−0.0001 (9)	−0.0009 (11)	0.0004 (8)
C1	0.0508 (12)	0.0408 (11)	0.0437 (11)	0.0019 (10)	−0.0031 (12)	−0.0007 (9)
C2	0.0483 (11)	0.0380 (10)	0.0460 (11)	−0.0029 (9)	0.0014 (11)	−0.0021 (9)
C3	0.0777 (15)	0.0465 (11)	0.0451 (11)	−0.0146 (11)	−0.0028 (13)	0.0018 (10)
C4	0.0586 (13)	0.0472 (11)	0.0415 (10)	−0.0079 (11)	−0.0026 (12)	−0.0003 (10)
C5	0.0699 (15)	0.0461 (12)	0.0635 (14)	0.0064 (12)	0.0128 (13)	0.0032 (11)
C6	0.0559 (13)	0.0546 (12)	0.0570 (14)	0.0007 (12)	0.0147 (12)	0.0098 (12)
C7	0.0496 (12)	0.0444 (11)	0.0471 (11)	−0.0031 (10)	−0.0049 (12)	0.0088 (10)
C8	0.0538 (14)	0.0585 (13)	0.0649 (14)	0.0130 (12)	0.0075 (14)	0.0120 (12)
C9	0.0514 (13)	0.0703 (15)	0.0563 (14)	−0.0020 (12)	0.0105 (12)	0.0134 (12)
C10	0.0730 (16)	0.0474 (11)	0.0698 (13)	0.0002 (13)	0.0112 (15)	−0.0183 (11)
C11	0.0631 (14)	0.0418 (11)	0.0544 (13)	0.0020 (11)	0.0010 (13)	−0.0077 (10)
C12	0.138 (3)	0.0831 (18)	0.0616 (17)	−0.036 (2)	−0.002 (2)	−0.0094 (15)
C13	0.163 (4)	0.088 (2)	0.0770 (19)	−0.036 (2)	0.021 (2)	0.0098 (18)
C14	0.106 (2)	0.0549 (14)	0.111 (2)	−0.0181 (16)	0.009 (2)	−0.0092 (17)
C15	0.104 (2)	0.0669 (16)	0.096 (2)	−0.0152 (18)	−0.025 (2)	−0.0109 (17)
C16	0.0863 (18)	0.0553 (14)	0.0645 (15)	−0.0028 (14)	−0.0128 (16)	−0.0006 (13)

O1—C1	1.203 (2)	C6—H6A	0.9300
O2—C1	1.331 (2)	C7—C8	1.369 (3)
O2—C10	1.452 (2)	C8—C9	1.377 (3)
O3—C7	1.365 (2)	C8—H8A	0.9300
O3—H3	0.93 (3)	C9—H9A	0.9300
N1—C2	1.467 (3)	C10—C11	1.496 (3)
N1—H1A	0.88 (2)	C10—H10A	0.9700
N1—H1B	0.94 (3)	C10—H10B	0.9700
C1—C2	1.508 (3)	C11—C16	1.359 (3)
C2—C3	1.536 (3)	C11—C12	1.371 (4)
C2—H2A	0.9800	C12—C13	1.384 (5)
C3—C4	1.506 (3)	C12—H12A	0.9300
C3—H3B	0.9700	C13—C14	1.348 (5)
C3—H3C	0.9700	C13—H13A	0.9300
C4—C9	1.374 (3)	C14—C15	1.341 (4)
C4—C5	1.381 (3)	C14—H14A	0.9300
C5—C6	1.377 (3)	C15—C16	1.377 (4)
C5—H5A	0.9300	C15—H15A	0.9300
C6—C7	1.369 (3)	C16—H16A	0.9300
C1—O2—C10	116.97 (16)	C8—C7—C6	118.71 (18)
C7—O3—H3	111.3 (16)	C7—C8—C9	120.4 (2)
C2—N1—H1A	109.5 (15)	C7—C8—H8A	119.8
C2—N1—H1B	109.9 (16)	C9—C8—H8A	119.8
H1A—N1—H1B	108 (3)	C4—C9—C8	121.9 (2)
O1—C1—O2	124.43 (19)	C4—C9—H9A	119.0
O1—C1—C2	124.95 (19)	C8—C9—H9A	119.0
O2—C1—C2	110.58 (18)	O2—C10—C11	107.02 (19)
N1—C2—C1	113.15 (16)	O2—C10—H10A	110.3
N1—C2—C3	107.82 (16)	C11—C10—H10A	110.3
C1—C2—C3	109.55 (17)	O2—C10—H10B	110.3
N1—C2—H2A	108.7	C11—C10—H10B	110.3
C1—C2—H2A	108.7	H10A—C10—H10B	108.6
C3—C2—H2A	108.7	C16—C11—C12	118.0 (2)
C4—C3—C2	115.65 (16)	C16—C11—C10	121.4 (2)
C4—C3—H3B	108.4	C12—C11—C10	120.6 (2)
C2—C3—H3B	108.4	C11—C12—C13	120.2 (3)
C4—C3—H3C	108.4	C11—C12—H12A	119.9
C2—C3—H3C	108.4	C13—C12—H12A	119.9
H3B—C3—H3C	107.4	C14—C13—C12	120.7 (3)
C9—C4—C5	116.71 (19)	C14—C13—H13A	119.6
C9—C4—C3	122.1 (2)	C12—C13—H13A	119.6
C5—C4—C3	121.2 (2)	C15—C14—C13	119.4 (3)
C6—C5—C4	121.8 (2)	C15—C14—H14A	120.3
C6—C5—H5A	119.1	C13—C14—H14A	120.3
C4—C5—H5A	119.1	C14—C15—C16	120.6 (3)
C7—C6—C5	120.4 (2)	C14—C15—H15A	119.7
C7—C6—H6A	119.8	C16—C15—H15A	119.7
C5—C6—H6A	119.8	C11—C16—C15	121.1 (3)
O3—C7—C8	118.5 (2)	C11—C16—H16A	119.4
O3—C7—C6	122.7 (2)	C15—C16—H16A	119.4
C10—O2—C1—O1	−4.7 (3)	C6—C7—C8—C9	0.7 (3)
C10—O2—C1—C2	173.19 (16)	C5—C4—C9—C8	0.6 (3)
O1—C1—C2—N1	−41.7 (3)	C3—C4—C9—C8	−180.0 (2)
O2—C1—C2—N1	140.49 (19)	C7—C8—C9—C4	−0.8 (4)
O1—C1—C2—C3	78.7 (2)	C1—O2—C10—C11	−174.17 (19)
O2—C1—C2—C3	−99.2 (2)	O2—C10—C11—C16	−119.4 (2)
N1—C2—C3—C4	−177.03 (19)	O2—C10—C11—C12	59.8 (3)
C1—C2—C3—C4	59.4 (3)	C16—C11—C12—C13	−1.1 (4)
C2—C3—C4—C9	−87.4 (3)	C10—C11—C12—C13	179.6 (3)
C2—C3—C4—C5	92.1 (2)	C11—C12—C13—C14	1.0 (6)
C9—C4—C5—C6	−0.2 (3)	C12—C13—C14—C15	−0.3 (6)
C3—C4—C5—C6	−179.7 (2)	C13—C14—C15—C16	−0.1 (5)
C4—C5—C6—C7	0.1 (4)	C12—C11—C16—C15	0.7 (4)
C5—C6—C7—O3	−178.8 (2)	C10—C11—C16—C15	179.9 (2)
C5—C6—C7—C8	−0.3 (3)	C14—C15—C16—C11	−0.1 (4)
O3—C7—C8—C9	179.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1i	0.93 (3)	1.82 (3)	2.718 (3)	163 (2)
N1—H1A···O1ii	0.88 (2)	2.21 (3)	3.030 (3)	156 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N1i	0.93 (3)	1.82 (3)	2.718 (3)	163 (2)
N1—H1A⋯O1ii	0.88 (2)	2.21 (3)	3.030 (3)	156 (2)

Symmetry codes: (i) ; (ii) .