N-(4-Isopropoxyphen­yl)acetamide

Zhang, M.; Lu, R.-Z.; Han, L.-N.; Wei, W.-B.; Wang, H.-B.

doi:10.1107/S1600536809012665

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1017

doi:10.1107/S1600536809012665

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N-(4-Isopropoxyphenyl)acetamide

Min Zhang,^a,^b Ran-Zhe Lu,^a,^b Lu-Na Han,^a,^b Wen-Bin Wei ^a,^b and Hai-Bo Wang ^a ^*

^aCollege of Light Industry and Food Science, Nanjing University of Technology, Xinmofan Road No.5 Nanjing, Nanjing 210009, People's Republic of China, and ^bCollege of Science, Nanjing University of Technology, Xinmofan Road No.5 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: wanghaibo@njut.edu.cn

(Received 31 March 2009; accepted 3 April 2009; online 10 April 2009)

In the molecule of the title compound, C₁₁H₁₅NO₂, the planar acetamide unit [maximum deviation of 0.0014 (6) Å] is oriented at a dihedral angle of 19.68 (4)° with respect to the aromatic ring. An intramolecular C—H⋯O interaction results in the formation of a six-membered ring. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules into chains along the a axis

Related literature

For general background, see: Knesl et al. (2006 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₁H₁₅NO₂
M_r = 193.24
Orthorhombic, P b c a
a = 9.3010 (19) Å
b = 7.6490 (15) Å
c = 31.394 (6) Å
V = 2233.5 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 294 K
0.30 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.977, T_max = 0.992
2026 measured reflections
2026 independent reflections
1099 reflections with I > 2σ(I)
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.202
S = 1.01
2026 reflections
127 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0A⋯O2ⁱ	0.86	2.01	2.869 (3)	175
C6—H6A⋯O2	0.93	2.34	2.892 (4)	118
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ) and ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks D, I. DOI: 10.1107/S1600536809012665/hk2659sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809012665/hk2659Isup2.hkl

checkCIF report

Comment top

As part of our ongoing studies on tandutinib (Knesl et al., 2006), we report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Ring A (C4-C9) is, of course, planar. The B (O2/N/C10/C11) moiety is also planar with a maximum deviation of -0.0014 (6) Å for C10 atom, and it is oriented with respect to ring A at a dihedral angle of 19.68 (4)°. Intramolecular C-H···O interaction (Table 1) results in the formation of a six-membered ring C (O2/N/C6/C7/C10/H6A), having twisted conformation.

In the crystal structure, intermolecular N-H···O hydrogen bonds (Table 1) link the molecules into chains along the a axis, in which they may be effective in the stabilization of the structure.

Related literature top

For general background, see: Knesl et al. (2006). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, N-(4-hydroxyphenyl)acetamide (50 mmol), 2-bromopropane (75 mmol) and potassium hydroxide (100 mmol) were mixed with ethanol (60 ml), and then the mixture was heated to reflux. Reaction progress was monitored by TLC. After ethanol removed in vacuo and filtration, the title compound was obtained (yield; 83.2%, m.p. 403 K). Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethyl acetate solution.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Hydrogen bond is shown as dashed line.

N-(4-isopropoxyphenyl)acetamide top

Crystal data top

C₁₁H₁₅NO₂	D_x = 1.149 Mg m⁻³
M_r = 193.24	Melting point: 403K K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 9.3010 (19) Å	θ = 9–12°
b = 7.6490 (15) Å	µ = 0.08 mm⁻¹
c = 31.394 (6) Å	T = 294 K
V = 2233.5 (8) Å³	Block, colorless
Z = 8	0.30 × 0.10 × 0.10 mm
F(000) = 832

Data collection top

Enraf–Nonius CAD-4 diffractometer	1099 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 25.3°, θ_min = 1.3°
ω/2θ scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = 0→9
T_min = 0.977, T_max = 0.992	l = 0→37
2026 measured reflections	3 standard reflections every 120 min
2026 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.068	H-atom parameters constrained
wR(F²) = 0.202	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
2026 reflections	Δρ_max = 0.26 e Å⁻³
127 parameters	Δρ_min = −0.23 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₁H₁₅NO₂	V = 2233.5 (8) Å³
M_r = 193.24	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.3010 (19) Å	µ = 0.08 mm⁻¹
b = 7.6490 (15) Å	T = 294 K
c = 31.394 (6) Å	0.30 × 0.10 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1099 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.000
T_min = 0.977, T_max = 0.992	3 standard reflections every 120 min
2026 measured reflections	intensity decay: 1%
2026 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	127 parameters
wR(F²) = 0.202	H-atom parameters constrained
S = 1.01	Δρ_max = 0.26 e Å⁻³
2026 reflections	Δρ_min = −0.23 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N	0.5437 (3)	0.2110 (3)	0.52353 (8)	0.0516 (7)
H0A	0.4609	0.2564	0.5183	0.062*
O1	0.5722 (3)	−0.0692 (3)	0.68713 (7)	0.0834 (8)
O2	0.7614 (2)	0.1579 (3)	0.49473 (7)	0.0665 (7)
C1	0.5187 (7)	−0.3739 (7)	0.67643 (15)	0.128 (2)
H1A	0.5192	−0.3613	0.6460	0.192*
H1B	0.4231	−0.3546	0.6870	0.192*
H1C	0.5494	−0.4897	0.6839	0.192*
C2	0.6254 (7)	−0.2587 (7)	0.74329 (13)	0.1163 (17)
H2A	0.6915	−0.1733	0.7542	0.175*
H2B	0.6577	−0.3737	0.7510	0.175*
H2C	0.5318	−0.2385	0.7552	0.175*
C3	0.6181 (5)	−0.2437 (6)	0.69566 (12)	0.0810 (12)
H3A	0.7146	−0.2607	0.6838	0.097*
C4	0.5728 (4)	−0.0080 (4)	0.64580 (11)	0.0602 (9)
C5	0.6698 (3)	−0.0586 (4)	0.61512 (10)	0.0589 (9)
H5A	0.7396	−0.1415	0.6215	0.071*
C6	0.6637 (3)	0.0134 (4)	0.57479 (10)	0.0543 (8)
H6A	0.7297	−0.0221	0.5543	0.065*
C7	0.5608 (3)	0.1378 (4)	0.56435 (9)	0.0470 (8)
C8	0.4652 (4)	0.1886 (5)	0.59609 (12)	0.0631 (10)
H8A	0.3955	0.2722	0.5900	0.076*
C9	0.4712 (4)	0.1183 (5)	0.63610 (11)	0.0680 (10)
H9A	0.4069	0.1555	0.6569	0.082*
C10	0.6390 (3)	0.2191 (4)	0.49183 (10)	0.0515 (8)
C11	0.5892 (4)	0.3070 (5)	0.45170 (11)	0.0638 (10)
H11A	0.6652	0.3047	0.4310	0.096*
H11B	0.5638	0.4260	0.4578	0.096*
H11C	0.5069	0.2464	0.4406	0.096*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N	0.0428 (13)	0.0549 (16)	0.0572 (16)	0.0014 (12)	−0.0018 (11)	0.0035 (13)
O1	0.119 (2)	0.0703 (17)	0.0608 (16)	0.0233 (16)	0.0052 (14)	0.0019 (13)
O2	0.0471 (13)	0.0715 (16)	0.0808 (16)	0.0047 (12)	0.0103 (12)	0.0115 (12)
C1	0.198 (6)	0.092 (4)	0.094 (4)	−0.034 (4)	0.005 (4)	0.003 (3)
C2	0.168 (5)	0.107 (4)	0.074 (3)	0.024 (4)	0.001 (3)	0.022 (3)
C3	0.096 (3)	0.069 (2)	0.078 (3)	0.014 (2)	0.008 (2)	0.011 (2)
C4	0.076 (2)	0.0508 (19)	0.054 (2)	0.0052 (19)	−0.0027 (17)	−0.0050 (16)
C5	0.061 (2)	0.051 (2)	0.065 (2)	0.0133 (17)	−0.0040 (16)	0.0000 (17)
C6	0.0534 (18)	0.0518 (19)	0.058 (2)	0.0022 (16)	0.0051 (15)	−0.0014 (16)
C7	0.0428 (15)	0.0439 (17)	0.0543 (19)	−0.0027 (14)	−0.0004 (13)	−0.0027 (14)
C8	0.062 (2)	0.057 (2)	0.071 (2)	0.0136 (17)	0.0049 (17)	0.0004 (18)
C9	0.076 (2)	0.064 (2)	0.063 (2)	0.017 (2)	0.0114 (17)	−0.0049 (19)
C10	0.0486 (17)	0.0420 (18)	0.064 (2)	−0.0084 (15)	0.0008 (15)	−0.0044 (15)
C11	0.061 (2)	0.063 (2)	0.067 (2)	−0.0106 (18)	−0.0042 (16)	0.0080 (18)

Geometric parameters (Å, º) top

N—C10	1.334 (4)	C4—C5	1.375 (4)
N—C7	1.407 (4)	C4—C9	1.385 (4)
N—H0A	0.8600	C5—C6	1.382 (4)
O1—C4	1.379 (4)	C5—H5A	0.9300
O1—C3	1.427 (5)	C6—C7	1.389 (4)
O2—C10	1.234 (4)	C6—H6A	0.9300
C1—C3	1.487 (6)	C7—C8	1.391 (4)
C1—H1A	0.9600	C8—C9	1.367 (5)
C1—H1B	0.9600	C8—H8A	0.9300
C1—H1C	0.9600	C9—H9A	0.9300
C2—C3	1.501 (5)	C10—C11	1.501 (4)
C2—H2A	0.9600	C11—H11A	0.9600
C2—H2B	0.9600	C11—H11B	0.9600
C2—H2C	0.9600	C11—H11C	0.9600
C3—H3A	0.9800

C10—N—C7	128.5 (3)	C4—C5—C6	120.2 (3)
C10—N—H0A	115.7	C4—C5—H5A	119.9
C7—N—H0A	115.7	C6—C5—H5A	119.9
C4—O1—C3	119.5 (3)	C5—C6—C7	121.2 (3)
C3—C1—H1A	109.5	C5—C6—H6A	119.4
C3—C1—H1B	109.5	C7—C6—H6A	119.4
H1A—C1—H1B	109.5	C6—C7—C8	117.6 (3)
C3—C1—H1C	109.5	C6—C7—N	124.4 (3)
H1A—C1—H1C	109.5	C8—C7—N	118.0 (3)
H1B—C1—H1C	109.5	C9—C8—C7	121.5 (3)
C3—C2—H2A	109.5	C9—C8—H8A	119.3
C3—C2—H2B	109.5	C7—C8—H8A	119.3
H2A—C2—H2B	109.5	C8—C9—C4	120.3 (3)
C3—C2—H2C	109.5	C8—C9—H9A	119.9
H2A—C2—H2C	109.5	C4—C9—H9A	119.9
H2B—C2—H2C	109.5	O2—C10—N	122.7 (3)
O1—C3—C1	111.3 (4)	O2—C10—C11	121.1 (3)
O1—C3—C2	105.8 (3)	N—C10—C11	116.2 (3)
C1—C3—C2	112.4 (4)	C10—C11—H11A	109.5
O1—C3—H3A	109.1	C10—C11—H11B	109.5
C1—C3—H3A	109.1	H11A—C11—H11B	109.5
C2—C3—H3A	109.1	C10—C11—H11C	109.5
C5—C4—O1	124.5 (3)	H11A—C11—H11C	109.5
C5—C4—C9	119.3 (3)	H11B—C11—H11C	109.5
O1—C4—C9	116.1 (3)

C4—O1—C3—C1	−65.9 (5)	C10—N—C7—C6	−21.2 (5)
C4—O1—C3—C2	171.7 (4)	C10—N—C7—C8	161.2 (3)
C3—O1—C4—C5	−32.2 (5)	C6—C7—C8—C9	−0.4 (5)
C3—O1—C4—C9	150.6 (4)	N—C7—C8—C9	177.4 (3)
O1—C4—C5—C6	−178.5 (3)	C7—C8—C9—C4	−0.8 (5)
C9—C4—C5—C6	−1.3 (5)	C5—C4—C9—C8	1.7 (5)
C4—C5—C6—C7	0.2 (5)	O1—C4—C9—C8	179.0 (3)
C5—C6—C7—C8	0.7 (5)	C7—N—C10—O2	0.6 (5)
C5—C6—C7—N	−176.9 (3)	C7—N—C10—C11	−179.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···O2ⁱ	0.86	2.01	2.869 (3)	175
C6—H6A···O2	0.93	2.34	2.892 (4)	118

Symmetry code: (i) x−1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₅NO₂
M_r	193.24
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	294
a, b, c (Å)	9.3010 (19), 7.6490 (15), 31.394 (6)
V (Å³)	2233.5 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.977, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	2026, 2026, 1099
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.202, 1.01
No. of reflections	2026
No. of parameters	127
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.23

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and ORTEP-3 (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···O2ⁱ	0.86	2.01	2.869 (3)	175
C6—H6A···O2	0.93	2.34	2.892 (4)	118

Symmetry code: (i) x−1/2, −y+1/2, −z+1.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft. The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Knesl, P., Roeseling, D. & Jordis, U. (2006). Molecules, 11, 286–297. Web of Science CrossRef PubMed CAS Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1017

doi:10.1107/S1600536809012665

Open

access