N-(4-Hydroxy­pheneth­yl)acetamide

Abstract

In the title compound, C₁₀H₁₃NO₂, the occurrence of inter­molecular N—H⋯O and O—H⋯O hydrogen bonds between the hydr­oxy and acetamido groups results in the formation of tetra­mers with an R ₄ ⁴(25) graph-set motif. These tetra­mers 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 _r = 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) ų

• 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

• Δρ_max = 0.16 e Å⁻³

• Δρ_min = −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 ▶).

Supplementary Material

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

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) .

supplementary crystallographic information

Comment

N-(4-Hydroxyphenethyl)acetamide displays various biological activities (Garcez et al., 2000; Montedoro et al., 1993; Allen et al., 1987), we report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig 1), all of the bond lengths and angles are within normal ranges. the occurrence of intermolecular N–H···O and O–H···O hydrogen bonds between the hydroxy and acetamido groups results in the formation of tetramers with a R₄⁴(25) graph set motif (Etter, 1990; Bernstein et al., 1995). These tetrameric motifs are further assemble to build up a corrugated sheet parallel to the (0 0 1) plane (Table 1, Fig. 2).

The bond lengths and bond angles agree with the values observed in related structures (Chai et al., 2009; Song et al., 2008).

Experimental

The title compound was separated from fermentation liquor as a white solid. Single crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol/water solution(2:1 v/v). ¹H NMR (DMSO-d₆, δ): 9.14 (1H, s, OH), 7.84 (1H, br, NH), 6.96 (2H, d, PhH₂), 6.66 (2H, d, PhH₂), 3.14–3.19 (2H, m, CH₂), 2.49–2.57 (2H, m, CH₂), 1.77 (3H, s, CH₃). MS(FAB, m/z): 180 (M+H)⁺.

Refinement

All H atom were placed at calculated positions, with C—H = 0.96–0.97 Å and N—H = 0.86 Å, and were included in the final cycles of refinement using a riding model, with U_iso(H) = 1.2 U_eq(C,N) or 1.5 U_eq(methyl C). The H of the methyl group were statistically disordered over two positions.

Figures

Fig. 1.

Molecular structure of (I) with the atos labeling scheme. Ellipsoids are drawn at the 30% probability level. H atoms are rpresented as small spheres of arbitrary radii.

Fig. 2.

Partial packing view showing the corrugated sheet and the R44(25) graph set motif.

Crystal data

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

Data collection

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

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

Special details

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 (Ų)

	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

Atomic displacement parameters (Ų)

	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)

Geometric parameters (Å, °)

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

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) −x+1, y+1/2, −z+1/2; (ii) x+1, y, z.