N-(4-Isopropoxyphen-yl)acetamide.

In the mol-ecule of the title compound, C(11)H(15)NO(2), 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 intra-molecular C-H⋯O inter-action results in the formation of a six-membered ring. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules 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 = 193.24

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.202

S = 1.01

2026 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.23 e Å−3

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 ▶).

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

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

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

C11H15NO2	Dx = 1.149 Mg m−3
Mr = 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

Enraf–Nonius CAD-4 diffractometer	1099 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.0000
graphite	θmax = 25.3°, θmin = 1.3°
ω/2θ scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = 0→9
Tmin = 0.977, Tmax = 0.992	l = 0→37
2026 measured reflections	3 standard reflections every 120 min
2026 independent reflections	intensity decay: 1%

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(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2026 reflections	Δρmax = 0.26 e Å−3
127 parameters	Δρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .