N-(4-Hydroxy­pheneth­yl)acetamide

Wang, B.; Chai, Y.; Tao, P.; Liu, M.

doi:10.1107/S1600536809025409

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1789

doi:10.1107/S1600536809025409

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N-(4-Hydroxyphenethyl)acetamide

Bo Wang,^a Yun Chai,^a Peizhen Tao ^a and Mingliang Liu ^a ^*

^aInstitute of Medicinal Biotechnology, Chinese Academy of Medical Sciences, and Peking Union Medical College, Beijing 100050, People's Republic of China
^*Correspondence e-mail: lmllyx@yahoo.com.cn

(Received 22 June 2009; accepted 1 July 2009; online 8 July 2009)

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 R₄⁴(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, P 2₁ /c
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[F² > 2σ(F²)] = 0.037
wR(F²) = 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

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) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x+1, y, z.

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).

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

For the biological activity of N-(4-yydroxyphenethyl)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 top

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)⁺.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); 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, 2008).

Figures top

	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.

N-(4-Hydroxyphenethyl)acetamide top

Crystal data top

C₁₀H₁₃NO₂	F(000) = 384
M_r = 179.21	D_x = 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 top

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

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0387P)² + 0.1837P] where P = (F_o² + 2F_c²)/3
1713 reflections	(Δ/σ)_max < 0.001
119 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₀H₁₃NO₂	V = 976.2 (2) Å³
M_r = 179.21	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.9206 (13) Å	µ = 0.09 mm⁻¹
b = 8.7861 (11) Å	T = 298 K
c = 11.4943 (16) Å	0.43 × 0.38 × 0.20 mm
β = 102.998 (1)°

Data collection top

Bruker SMART CCD diffractometer	1713 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	1196 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.978	R_int = 0.027
4753 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.05	Δρ_max = 0.16 e Å⁻³
1713 reflections	Δρ_min = −0.14 e Å⁻³
119 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	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 (Å²) top

	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, º) top

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, º) top

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.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₃NO₂
M_r	179.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	9.9206 (13), 8.7861 (11), 11.4943 (16)
β (°)	102.998 (1)
V (Å³)	976.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.43 × 0.38 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008)
T_min, T_max	0.961, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	4753, 1713, 1196
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.100, 1.05
No. of reflections	1713
No. of parameters	119
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.14

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Pearce et al., 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.08	2.9048 (18)	161.2
O1—H1A···O2ⁱⁱ	0.82	1.83	2.6464 (17)	174.0

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x+1, y, z.

Acknowledgements

This work was supported by the IMB Research Foundation. The authors thank Dr Daqi Wang for useful discussions.

References

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