N-(3,4-Diethoxy­phen­yl)acetamide

Ma, P.-H.; Zhou, K.-Z.; Sun, M.-L.; Zhao, X.-M.; Xiao, X.

doi:10.1107/S1600536809018042

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1314

doi:10.1107/S1600536809018042

Open

access

N-(3,4-Diethoxyphenyl)acetamide

Pei-Hua Ma,^a Kai-Zhi Zhou,^a Mei-Lian Sun,^a Xiu-Mei Zhao ^a and Xin Xiao ^a ^*

^aKey Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, People's Republic of China
^*Correspondence e-mail: gyhxxiaoxin@163.com

(Received 12 May 2009; accepted 13 May 2009; online 20 May 2009)

In the title compound, C₁₂H₁₇NO₃, the conformations of the N—H and C=O bonds are anti to each other. In the crystal structure, N—H⋯O hydrogen-bond interactions 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_r = 223.27
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.119
S = 1.08
2155 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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

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 ).

Supporting information

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

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

checkCIF report

Comment top

Acetamide is an important class of medical intermidate. Many biologically active compounds are synthesized by using acetamide (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 (Vega-Noverola et al., 1989). The crystal structure determination of the title compound (I) has been carried out in order to elucidate the molecular conformation.

The molecule of the title compound, (Fig. 1), consists of a phenylacetamide group and two ethoxyl groups. The conformations of the N—H and C=O bonds are anti to each other. The C10—C9—O2—C4 and C8—C7—O1—C3 torsion angles are -173.61 (15)° and 178.46 (15)°, respectively. The title compound forms intermolecular H bonds whereas the N1 act as hydrogen-bond donor and the O3 act as hydrogen-bond acceptor, the distance of the N1—H1···O3 hydrogen bond is 2.915 (2) Å (Table 1). In the crystal structure, N—H···O hydrogen bonds interactions may help to establish the packing.

Related literature top

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 top

Ferrous powder (2.20 g, 0.039 mol), water (15 ml) and acetic acid (3 ml) were reflux for 4 h, the reaction mixture was cooled to room temperature. Then a solution of 1,2-diethoxy-4-nitrobenzene (2.10 g, 0.01 mol) in acetic acid (50 ml) was added to the mixture, the solution was reflux for 6 h. the mixture was filtered, and the resulting solution was added to water (150 ml), much white precipitate was appeared, the mixture was filtered again, the solid product was dissolved in 80 ml ethanol. and then set aside for five days to obtain colourless crystals [yield: 53%].

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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).

Figures top

Fig. 1. The molecular structure of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

N-(3,4-Diethoxyphenyl)acetamide top

Crystal data top

C₁₂H₁₇NO₃	F(000) = 480
M_r = 223.27	D_x = 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

Data collection top

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

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0639P)²] where P = (F_o² + 2F_c²)/3
2155 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₂H₁₇NO₃	V = 1227.8 (14) Å³
M_r = 223.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.563 (8) Å	µ = 0.09 mm⁻¹
b = 8.661 (6) Å	T = 293 K
c = 9.305 (7) Å	0.24 × 0.21 × 0.20 mm
β = 101.773 (14)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2155 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1570 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.975	R_int = 0.034
6295 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.08	Δρ_max = 0.16 e Å⁻³
2155 reflections	Δρ_min = −0.25 e Å⁻³
145 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
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₇NO₃
M_r	223.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	15.563 (8), 8.661 (6), 9.305 (7)
β (°)	101.773 (14)
V (Å³)	1227.8 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.24 × 0.21 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.971, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	6295, 2155, 1570
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.119, 1.08
No. of reflections	2155
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.25

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.86	2.08	2.915 (2)	163.6

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

The authors gratefully acknowledge the Natural Science Foundation of China (No. 20767001), the International Collaborative Project of Guizhou Province andthe Governor Foundation of Guizhou Province for financial support.

References

Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Koike, K., Jia, Z., Nikaido, T., Liu, Y., Zhao, Y. & Guo, D. (1999). Org. Lett. 1, 197–198. Web of Science CrossRef CAS Google Scholar
Saeed, A., Khera, R. A., Abbas, N., Simpson, J. & Stanley, R. G. (2008). Acta Cryst. E64, o2322–o2323. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vega-Noverola, A. P., Soto, J. M., Noguera, F. P., Mauri, J. M. & Spickett, G. W. R. (1989). US Patent No. 4 877 780. Google Scholar