N-(3,4-Diethoxy-phen-yl)acetamide.

In the title compound, C(12)H(17)NO(3), the conformations of the N-H and C=O bonds are anti to each other. In the crystal structure, N-H⋯O hydrogen-bond inter-actions help to establish the packing.

Related literature

For the use of acetamides in the synthesis of biologically active compounds, see: Koike et al. (1999 ▶). The benzanilide core is present in compounds with a wide range of biological activity and benzanilides and benzamides are also used extensively in organic synthesis (Saeed et al., 2008 ▶). Various N-substituted benzamides exhibit potent anti­emetic activity, see: Vega-Noverola et al. (1989 ▶).

Experimental

Crystal data

C12H17NO3

M = 223.27

Monoclinic,

a = 15.563 (8) Å

b = 8.661 (6) Å

c = 9.305 (7) Å

β = 101.773 (14)°

V = 1227.8 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.24 × 0.21 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.971, T max = 0.975

6295 measured reflections

2155 independent reflections

1570 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.119

S = 1.08

2155 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809018042/at2786sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018042/at2786Isup2.hkl

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

C12H17NO3	F(000) = 480
Mr = 223.27	Dx = 1.208 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2155 reflections
a = 15.563 (8) Å	θ = 1.3–25.0°
b = 8.661 (6) Å	µ = 0.09 mm−1
c = 9.305 (7) Å	T = 293 K
β = 101.773 (14)°	Block, colourless
V = 1227.8 (14) Å3	0.24 × 0.21 × 0.20 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2155 independent reflections
Radiation source: fine-focus sealed tube	1570 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −18→16
Tmin = 0.971, Tmax = 0.975	k = −10→10
6295 measured reflections	l = −10→11

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0639P)2] where P = (Fo2 + 2Fc2)/3
2155 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.25 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
C1	0.36147 (10)	0.08455 (17)	0.48242 (16)	0.0426 (4)
C2	0.32424 (10)	0.07894 (18)	0.60656 (15)	0.0451 (4)
H2	0.3519	0.1289	0.6920	0.054*
C3	0.24680 (10)	0.00019 (18)	0.60451 (16)	0.0445 (4)
C4	0.20432 (11)	−0.07482 (19)	0.47506 (17)	0.0479 (4)
C5	0.24235 (11)	−0.0712 (2)	0.35439 (18)	0.0542 (5)
H5	0.2153	−0.1223	0.2693	0.065*
C6	0.32090 (11)	0.00790 (19)	0.35673 (17)	0.0513 (4)
H6	0.3458	0.0089	0.2739	0.062*
C7	0.24108 (11)	0.0806 (2)	0.84850 (17)	0.0554 (5)
H7A	0.2403	0.1891	0.8225	0.067*
H7B	0.3013	0.0508	0.8887	0.067*
C8	0.18566 (14)	0.0537 (3)	0.9582 (2)	0.0759 (6)
H8A	0.2081	0.1128	1.0451	0.114*
H8B	0.1866	−0.0541	0.9827	0.114*
H8C	0.1265	0.0850	0.9179	0.114*
C9	0.06962 (12)	−0.1888 (2)	0.3449 (2)	0.0656 (5)
H9A	0.0967	−0.2673	0.2944	0.079*
H9B	0.0573	−0.0991	0.2817	0.079*
C10	−0.01353 (12)	−0.2493 (3)	0.3827 (3)	0.0869 (7)
H10A	−0.0539	−0.2776	0.2942	0.130*
H10B	−0.0394	−0.1707	0.4330	0.130*
H10C	−0.0004	−0.3382	0.4449	0.130*
C11	0.48850 (10)	0.20423 (18)	0.39666 (17)	0.0446 (4)
C12	0.56454 (11)	0.3114 (2)	0.44698 (19)	0.0569 (5)
H12A	0.5671	0.3393	0.5476	0.085*
H12B	0.5570	0.4026	0.3872	0.085*
H12C	0.6181	0.2606	0.4383	0.085*
N1	0.43955 (8)	0.17335 (14)	0.49706 (14)	0.0459 (4)
H1	0.4583	0.2131	0.5824	0.055*
O1	0.20629 (7)	−0.01068 (13)	0.72098 (11)	0.0559 (4)
O2	0.12688 (7)	−0.14790 (14)	0.48136 (13)	0.0626 (4)
O3	0.47167 (8)	0.15207 (13)	0.27060 (12)	0.0587 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0448 (9)	0.0439 (9)	0.0407 (8)	0.0034 (7)	0.0126 (7)	0.0045 (7)
C2	0.0490 (10)	0.0488 (9)	0.0385 (9)	−0.0023 (7)	0.0114 (7)	−0.0007 (7)
C3	0.0481 (10)	0.0458 (9)	0.0427 (9)	−0.0007 (7)	0.0162 (7)	0.0006 (7)
C4	0.0476 (10)	0.0486 (10)	0.0475 (9)	−0.0042 (8)	0.0103 (7)	−0.0004 (7)
C5	0.0615 (11)	0.0593 (11)	0.0419 (9)	−0.0073 (9)	0.0105 (8)	−0.0074 (8)
C6	0.0602 (11)	0.0569 (10)	0.0398 (9)	−0.0008 (8)	0.0174 (8)	−0.0008 (8)
C7	0.0614 (11)	0.0640 (11)	0.0437 (9)	−0.0105 (9)	0.0172 (8)	−0.0088 (8)
C8	0.0879 (15)	0.0933 (15)	0.0524 (11)	−0.0225 (12)	0.0279 (10)	−0.0150 (10)
C9	0.0592 (12)	0.0656 (12)	0.0658 (12)	−0.0083 (9)	−0.0018 (9)	−0.0002 (9)
C10	0.0583 (13)	0.0939 (17)	0.1049 (17)	−0.0174 (12)	0.0083 (12)	−0.0065 (13)
C11	0.0517 (10)	0.0432 (9)	0.0422 (9)	0.0096 (7)	0.0169 (7)	0.0094 (7)
C12	0.0590 (11)	0.0557 (10)	0.0611 (11)	−0.0030 (8)	0.0239 (9)	0.0089 (8)
N1	0.0501 (8)	0.0527 (8)	0.0375 (7)	−0.0036 (6)	0.0151 (6)	0.0004 (6)
O1	0.0606 (8)	0.0681 (8)	0.0443 (6)	−0.0172 (6)	0.0226 (6)	−0.0093 (6)
O2	0.0585 (8)	0.0752 (9)	0.0550 (7)	−0.0218 (6)	0.0133 (6)	−0.0094 (6)
O3	0.0723 (8)	0.0664 (8)	0.0423 (7)	0.0002 (6)	0.0231 (6)	0.0029 (5)

C1—C6	1.380 (2)	C8—H8B	0.9600
C1—C2	1.395 (2)	C8—H8C	0.9600
C1—N1	1.421 (2)	C9—O2	1.439 (2)
C2—C3	1.382 (2)	C9—C10	1.503 (3)
C2—H2	0.9300	C9—H9A	0.9700
C3—O1	1.3636 (19)	C9—H9B	0.9700
C3—C4	1.409 (2)	C10—H10A	0.9600
C4—C5	1.372 (2)	C10—H10B	0.9600
C4—O2	1.3732 (19)	C10—H10C	0.9600
C5—C6	1.398 (2)	C11—O3	1.2342 (19)
C5—H5	0.9300	C11—N1	1.3471 (19)
C6—H6	0.9300	C11—C12	1.502 (2)
C7—O1	1.437 (2)	C12—H12A	0.9600
C7—C8	1.483 (2)	C12—H12B	0.9600
C7—H7A	0.9700	C12—H12C	0.9600
C7—H7B	0.9700	N1—H1	0.8600
C8—H8A	0.9600
C6—C1—C2	119.30 (15)	H8A—C8—H8C	109.5
C6—C1—N1	125.16 (14)	H8B—C8—H8C	109.5
C2—C1—N1	115.54 (13)	O2—C9—C10	106.70 (16)
C3—C2—C1	120.95 (14)	O2—C9—H9A	110.4
C3—C2—H2	119.5	C10—C9—H9A	110.4
C1—C2—H2	119.5	O2—C9—H9B	110.4
O1—C3—C2	124.51 (14)	C10—C9—H9B	110.4
O1—C3—C4	115.80 (14)	H9A—C9—H9B	108.6
C2—C3—C4	119.69 (14)	C9—C10—H10A	109.5
C5—C4—O2	125.06 (15)	C9—C10—H10B	109.5
C5—C4—C3	118.91 (15)	H10A—C10—H10B	109.5
O2—C4—C3	116.03 (14)	C9—C10—H10C	109.5
C4—C5—C6	121.37 (15)	H10A—C10—H10C	109.5
C4—C5—H5	119.3	H10B—C10—H10C	109.5
C6—C5—H5	119.3	O3—C11—N1	123.10 (16)
C1—C6—C5	119.75 (15)	O3—C11—C12	121.56 (15)
C1—C6—H6	120.1	N1—C11—C12	115.32 (14)
C5—C6—H6	120.1	C11—C12—H12A	109.5
O1—C7—C8	107.94 (14)	C11—C12—H12B	109.5
O1—C7—H7A	110.1	H12A—C12—H12B	109.5
C8—C7—H7A	110.1	C11—C12—H12C	109.5
O1—C7—H7B	110.1	H12A—C12—H12C	109.5
C8—C7—H7B	110.1	H12B—C12—H12C	109.5
H7A—C7—H7B	108.4	C11—N1—C1	129.38 (14)
C7—C8—H8A	109.5	C11—N1—H1	115.3
C7—C8—H8B	109.5	C1—N1—H1	115.3
H8A—C8—H8B	109.5	C3—O1—C7	117.45 (13)
C7—C8—H8C	109.5	C4—O2—C9	117.83 (13)
C6—C1—C2—C3	−1.1 (2)	C4—C5—C6—C1	−0.2 (3)
N1—C1—C2—C3	178.02 (13)	O3—C11—N1—C1	−2.1 (2)
C1—C2—C3—O1	−179.99 (14)	C12—C11—N1—C1	176.25 (14)
C1—C2—C3—C4	−0.4 (2)	C6—C1—N1—C11	1.4 (2)
O1—C3—C4—C5	−178.74 (14)	C2—C1—N1—C11	−177.71 (14)
C2—C3—C4—C5	1.7 (2)	C2—C3—O1—C7	7.5 (2)
O1—C3—C4—O2	0.8 (2)	C4—C3—O1—C7	−172.04 (14)
C2—C3—C4—O2	−178.79 (14)	C8—C7—O1—C3	178.46 (15)
O2—C4—C5—C6	179.12 (15)	C5—C4—O2—C9	−17.2 (2)
C3—C4—C5—C6	−1.4 (3)	C3—C4—O2—C9	163.33 (15)
C2—C1—C6—C5	1.4 (2)	C10—C9—O2—C4	−173.61 (15)
N1—C1—C6—C5	−177.64 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.86	2.08	2.915 (2)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.86	2.08	2.915 (2)	164

Symmetry code: (i) .