N-(4-Hydroxy-pheneth-yl)acetamide.

In the title compound, C(10)H(13)NO(2), the occurrence of inter-molecular N-H⋯O and O-H⋯O hydrogen bonds between the hydr-oxy and acetamido groups results in the formation of tetra-mers with an R(4) (4)(25) graph-set motif. These tetra-mers are further assembled, building up a corrugated sheet parallel to (001).

Related literature

For the biological activity of N-(4-hydroxypheneth­yl)acetamide, see: Garcez et al. (2000 ▶); Montedoro et al. (1993 ▶). For related structures, see: Chai et al. (2009 ▶); Song et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶); Etter (1990 ▶)

Experimental

Crystal data

C10H13NO2

M = 179.21

Monoclinic,

a = 9.9206 (13) Å

b = 8.7861 (11) Å

c = 11.4943 (16) Å

β = 102.9980 (10)°

V = 976.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.43 × 0.38 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.961, T max = 0.978

4753 measured reflections

1713 independent reflections

1196 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.100

S = 1.05

1713 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and CAMERON (Pearce et al., 2000 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025409/dn2469sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025409/dn2469Isup2.hkl

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

C10H13NO2	F(000) = 384
Mr = 179.21	Dx = 1.219 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1622 reflections
a = 9.9206 (13) Å	θ = 3.0–26.2°
b = 8.7861 (11) Å	µ = 0.09 mm−1
c = 11.4943 (16) Å	T = 298 K
β = 102.998 (1)°	Block, colorless
V = 976.2 (2) Å3	0.43 × 0.38 × 0.20 mm
Z = 4

Bruker SMART CCD diffractometer	1713 independent reflections
Radiation source: fine-focus sealed tube	1196 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −7→11
Tmin = 0.961, Tmax = 0.978	k = −9→10
4753 measured reflections	l = −13→13

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0387P)2 + 0.1837P] where P = (Fo2 + 2Fc2)/3
1713 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.14 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	Occ. (<1)
N1	0.15094 (14)	0.38049 (16)	0.35383 (14)	0.0553 (4)
H1	0.1936	0.4303	0.3086	0.066*
O1	0.72697 (12)	0.10975 (15)	0.27285 (11)	0.0598 (4)
H1A	0.7957	0.1586	0.3049	0.090*
O2	−0.04072 (13)	0.25522 (17)	0.36772 (12)	0.0724 (4)
C1	0.40477 (16)	0.18477 (19)	0.44391 (14)	0.0444 (4)
C2	0.39022 (17)	0.09127 (19)	0.34533 (15)	0.0516 (5)
H2	0.3057	0.0435	0.3162	0.062*
C3	0.49703 (18)	0.0664 (2)	0.28865 (16)	0.0516 (5)
H3	0.4843	0.0024	0.2226	0.062*
C4	0.62273 (16)	0.13710 (18)	0.33044 (14)	0.0430 (4)
C5	0.64007 (17)	0.23153 (18)	0.42830 (14)	0.0462 (4)
H5	0.7244	0.2800	0.4568	0.055*
C6	0.53229 (17)	0.25403 (19)	0.48397 (15)	0.0493 (4)
H6	0.5455	0.3175	0.5503	0.059*
C7	0.28890 (18)	0.2102 (2)	0.50690 (16)	0.0542 (5)
H7A	0.3257	0.2034	0.5924	0.065*
H7B	0.2210	0.1299	0.4845	0.065*
C8	0.21757 (18)	0.3629 (2)	0.47851 (17)	0.0562 (5)
H8A	0.1488	0.3745	0.5260	0.067*
H8B	0.2854	0.4434	0.5012	0.067*
C9	0.02736 (18)	0.3236 (2)	0.30588 (17)	0.0545 (5)
C10	−0.0253 (2)	0.3440 (3)	0.17442 (18)	0.0790 (6)
H10A	0.0416	0.3994	0.1425	0.119*	0.50
H10B	−0.1108	0.3995	0.1597	0.119*	0.50
H10C	−0.0404	0.2461	0.1366	0.119*	0.50
H10D	−0.1146	0.2973	0.1501	0.119*	0.50
H10E	0.0377	0.2972	0.1329	0.119*	0.50
H10F	−0.0326	0.4506	0.1559	0.119*	0.50

	U11	U22	U33	U12	U13	U23
N1	0.0394 (8)	0.0592 (9)	0.0710 (10)	0.0001 (7)	0.0200 (7)	0.0143 (8)
O1	0.0472 (7)	0.0672 (9)	0.0692 (9)	−0.0047 (6)	0.0223 (6)	−0.0153 (6)
O2	0.0500 (8)	0.0981 (11)	0.0736 (9)	−0.0201 (7)	0.0232 (7)	0.0017 (8)
C1	0.0399 (9)	0.0478 (9)	0.0461 (10)	0.0014 (8)	0.0112 (7)	0.0084 (8)
C2	0.0393 (10)	0.0572 (11)	0.0565 (11)	−0.0115 (8)	0.0069 (8)	0.0006 (9)
C3	0.0503 (10)	0.0547 (11)	0.0492 (10)	−0.0075 (9)	0.0102 (8)	−0.0085 (8)
C4	0.0383 (9)	0.0445 (9)	0.0473 (10)	0.0017 (7)	0.0119 (7)	0.0022 (7)
C5	0.0348 (9)	0.0495 (10)	0.0521 (10)	−0.0034 (7)	0.0050 (7)	−0.0044 (8)
C6	0.0450 (10)	0.0542 (11)	0.0484 (10)	−0.0013 (8)	0.0096 (8)	−0.0073 (8)
C7	0.0475 (10)	0.0627 (12)	0.0545 (11)	−0.0009 (9)	0.0157 (8)	0.0079 (9)
C8	0.0439 (10)	0.0601 (12)	0.0682 (12)	−0.0054 (9)	0.0201 (9)	−0.0046 (9)
C9	0.0422 (10)	0.0601 (11)	0.0651 (12)	0.0080 (9)	0.0202 (9)	0.0039 (9)
C10	0.0602 (13)	0.1059 (18)	0.0711 (14)	0.0112 (12)	0.0150 (11)	0.0090 (13)

N1—C9	1.324 (2)	C5—H5	0.9300
N1—C8	1.445 (2)	C6—H6	0.9300
N1—H1	0.8600	C7—C8	1.518 (2)
O1—C4	1.3686 (19)	C7—H7A	0.9700
O1—H1A	0.8200	C7—H7B	0.9700
O2—C9	1.240 (2)	C8—H8A	0.9700
C1—C2	1.381 (2)	C8—H8B	0.9700
C1—C6	1.386 (2)	C9—C10	1.494 (3)
C1—C7	1.507 (2)	C10—H10A	0.9600
C2—C3	1.380 (2)	C10—H10B	0.9600
C2—H2	0.9300	C10—H10C	0.9600
C3—C4	1.379 (2)	C10—H10D	0.9600
C3—H3	0.9300	C10—H10E	0.9600
C4—C5	1.377 (2)	C10—H10F	0.9600
C5—C6	1.378 (2)
C9—N1—C8	123.14 (15)	N1—C8—H8A	108.9
C9—N1—H1	118.4	C7—C8—H8A	108.9
C8—N1—H1	118.4	N1—C8—H8B	108.9
C4—O1—H1A	109.5	C7—C8—H8B	108.9
C2—C1—C6	116.94 (15)	H8A—C8—H8B	107.7
C2—C1—C7	122.18 (15)	O2—C9—N1	121.13 (17)
C6—C1—C7	120.88 (15)	O2—C9—C10	121.75 (17)
C3—C2—C1	122.12 (16)	N1—C9—C10	117.12 (17)
C3—C2—H2	118.9	C9—C10—H10A	109.5
C1—C2—H2	118.9	C9—C10—H10B	109.5
C4—C3—C2	119.64 (16)	H10A—C10—H10B	109.5
C4—C3—H3	120.2	C9—C10—H10C	109.5
C2—C3—H3	120.2	H10A—C10—H10C	109.5
O1—C4—C5	122.12 (14)	H10B—C10—H10C	109.5
O1—C4—C3	118.36 (15)	C9—C10—H10D	109.5
C5—C4—C3	119.52 (15)	H10A—C10—H10D	141.1
C4—C5—C6	119.89 (15)	H10B—C10—H10D	56.3
C4—C5—H5	120.1	H10C—C10—H10D	56.3
C6—C5—H5	120.1	C9—C10—H10E	109.5
C5—C6—C1	121.89 (16)	H10A—C10—H10E	56.3
C5—C6—H6	119.1	H10B—C10—H10E	141.1
C1—C6—H6	119.1	H10C—C10—H10E	56.3
C1—C7—C8	113.41 (14)	H10D—C10—H10E	109.5
C1—C7—H7A	108.9	C9—C10—H10F	109.5
C8—C7—H7A	108.9	H10A—C10—H10F	56.3
C1—C7—H7B	108.9	H10B—C10—H10F	56.3
C8—C7—H7B	108.9	H10C—C10—H10F	141.1
H7A—C7—H7B	107.7	H10D—C10—H10F	109.5
N1—C8—C7	113.25 (15)	H10E—C10—H10F	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.08	2.9048 (18)	161
O1—H1A···O2ii	0.82	1.83	2.6464 (17)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.08	2.9048 (18)	161
O1—H1A⋯O2ii	0.82	1.83	2.6464 (17)	174

Symmetry codes: (i) ; (ii) .