N-(1-Naphth­yl)acetoacetamide

Tai, X.-S.; Feng, Y.-M.; Zhang, H.-X.

doi:10.1107/S1600536808002638

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o531

doi:10.1107/S1600536808002638

Open

access

N-(1-Naphthyl)acetoacetamide

Xi-Shi Tai,^a ^* Yi-Min Feng ^a and Hua-Xiang Zhang ^a

^aDepartment of Chemistry, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: taixishi@lzu.edu.cn

(Received 23 January 2008; accepted 23 January 2008; online 30 January 2008)

The title compound, C₁₄H₁₃NO₂, exists in the keto form. An N—H⋯O hydrogen bond helps to establish the packing.

Related literature

For background, see: Huang et al. (2001 ).

Experimental

Crystal data

C₁₄H₁₃NO₂
M_r = 227.25
Monoclinic, P 2₁ /c
a = 17.856 (2) Å
b = 8.1076 (12) Å
c = 8.5153 (14) Å
β = 102.777 (2)°
V = 1202.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 (2) K
0.50 × 0.40 × 0.38 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.959, T_max = 0.969
5815 measured reflections
2116 independent reflections
1335 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.121
S = 1.05
2116 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.17 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	2.01	2.853 (2)	168
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808002638/hb2694sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808002638/hb2694Isup2.hkl

checkCIF report

Comment top

The europium(III) and terbium(III) complexes of beta-diketonato and related conjugated ligands have been studied as emitting materials for organic light emitting diodes (OLEDs) (e.g. Huang et al., 2001). However, the quantum efficiency of most these complexes are unfortunately still low. This may be due to inefficiency of the trpilet-triplet energy transfer in these complexes. Therefore, there is a need to design ligands which have better energy transfer properties when coordinated to the lanthanide metal ion. As part of our studies in this area, we now report the synthesis and structure of the title compound, (I).

In (I), the C=O bonds length are 1.226 (2)Å and 1.208 (2) Å, indicating that it exists in the keto form (Fig. 1) in the solid state.

In the crystal structure, the molecules are stabilized by an N—H···O intermolecular hydrogen bond (Table 1) leading to [001] chains.

Related literature top

For background, see: Huang et al. (2001).

Experimental top

A solution of 1-naphthaline (10 mmol) in 30 ml benzene was added to a solution of ethyl acetoacetate (10 mmol). The reaction mixture was refluxed for 2 h with stirring, then the resulting pale precipitate was obtained by filtration, washed several times with benzene and dried in vacuo (yield 89%). Colourless blocks of (I) were recrystallized from ethanol by slow evaporation. IR (KBr, cm^-1): 3242 (m, N—H), 1723 (s, CH₃C=O), 1665 (s, amide C=O).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing 30% probabiility ellipsoids (arbitrary spheres for the H atoms).

N-(1-Naphthyl)acetoacetamide top

Crystal data top

C₁₄H₁₃NO₂	F(000) = 480
M_r = 227.25	D_x = 1.256 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1643 reflections
a = 17.856 (2) Å	θ = 2.3–23.5°
b = 8.1076 (12) Å	µ = 0.08 mm⁻¹
c = 8.5153 (14) Å	T = 298 K
β = 102.777 (2)°	Block, colourless
V = 1202.2 (3) Å³	0.50 × 0.40 × 0.38 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2116 independent reflections
Radiation source: fine-focus sealed tube	1335 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −21→21
T_min = 0.959, T_max = 0.969	k = −9→6
5815 measured reflections	l = −10→10

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0402P)² + 0.3082P] where P = (F_o² + 2F_c²)/3
2116 reflections	(Δ/σ)_max < 0.001
155 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₄H₁₃NO₂	V = 1202.2 (3) Å³
M_r = 227.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.856 (2) Å	µ = 0.08 mm⁻¹
b = 8.1076 (12) Å	T = 298 K
c = 8.5153 (14) Å	0.50 × 0.40 × 0.38 mm
β = 102.777 (2)°

Data collection top

Bruker SMART CCD diffractometer	2116 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1335 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.969	R_int = 0.042
5815 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.05	Δρ_max = 0.15 e Å⁻³
2116 reflections	Δρ_min = −0.17 e Å⁻³
155 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
N1	0.21814 (9)	0.2430 (2)	0.4659 (2)	0.0487 (5)
H1	0.2099	0.2073	0.5557	0.058*
O1	0.16833 (8)	0.38359 (18)	0.23841 (18)	0.0561 (4)
O2	0.05169 (8)	0.08943 (19)	0.29965 (19)	0.0631 (5)
C1	0.16240 (11)	0.3270 (2)	0.3687 (3)	0.0429 (5)
C2	0.08902 (11)	0.3457 (2)	0.4262 (2)	0.0445 (5)
H2A	0.1011	0.3525	0.5428	0.053*
H2B	0.0642	0.4480	0.3845	0.053*
C3	0.03443 (11)	0.2049 (3)	0.3741 (2)	0.0453 (5)
C4	−0.04209 (12)	0.2179 (3)	0.4158 (3)	0.0648 (7)
H4A	−0.0724	0.1229	0.3757	0.097*
H4B	−0.0677	0.3157	0.3679	0.097*
H4C	−0.0355	0.2236	0.5307	0.097*
C5	0.29076 (11)	0.2094 (3)	0.4290 (2)	0.0451 (5)
C6	0.34536 (13)	0.3281 (3)	0.4510 (3)	0.0623 (6)
H6	0.3347	0.4324	0.4860	0.075*
C7	0.41772 (14)	0.2943 (4)	0.4212 (3)	0.0737 (8)
H7	0.4547	0.3769	0.4355	0.088*
C8	0.43444 (13)	0.1437 (3)	0.3720 (3)	0.0694 (7)
H8	0.4834	0.1227	0.3557	0.083*
C9	0.37919 (12)	0.0178 (3)	0.3450 (3)	0.0531 (6)
C10	0.30501 (11)	0.0509 (3)	0.3728 (2)	0.0460 (5)
C11	0.24937 (13)	−0.0750 (3)	0.3404 (3)	0.0631 (7)
H11	0.2006	−0.0558	0.3583	0.076*
C12	0.26597 (16)	−0.2243 (3)	0.2834 (4)	0.0827 (9)
H12	0.2284	−0.3057	0.2616	0.099*
C13	0.33885 (17)	−0.2560 (4)	0.2574 (4)	0.0852 (9)
H13	0.3496	−0.3584	0.2186	0.102*
C14	0.39381 (15)	−0.1396 (3)	0.2880 (3)	0.0719 (7)
H14	0.4424	−0.1634	0.2713	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0492 (10)	0.0576 (11)	0.0413 (10)	0.0042 (9)	0.0144 (8)	0.0041 (8)
O1	0.0621 (9)	0.0623 (10)	0.0472 (9)	0.0061 (7)	0.0196 (7)	0.0069 (8)
O2	0.0646 (10)	0.0575 (10)	0.0711 (11)	−0.0038 (8)	0.0237 (8)	−0.0201 (8)
C1	0.0510 (12)	0.0366 (11)	0.0421 (12)	−0.0014 (9)	0.0124 (10)	−0.0047 (10)
C2	0.0494 (12)	0.0423 (12)	0.0427 (12)	0.0050 (9)	0.0124 (9)	−0.0022 (9)
C3	0.0513 (12)	0.0463 (13)	0.0388 (12)	0.0039 (10)	0.0110 (10)	0.0022 (10)
C4	0.0586 (14)	0.0655 (16)	0.0763 (17)	−0.0046 (12)	0.0281 (13)	−0.0085 (13)
C5	0.0398 (11)	0.0541 (13)	0.0406 (12)	−0.0009 (10)	0.0072 (9)	0.0017 (10)
C6	0.0578 (14)	0.0590 (15)	0.0686 (16)	−0.0085 (12)	0.0109 (12)	−0.0098 (12)
C7	0.0507 (15)	0.0733 (19)	0.096 (2)	−0.0191 (13)	0.0133 (14)	−0.0021 (16)
C8	0.0432 (13)	0.084 (2)	0.0812 (18)	−0.0005 (13)	0.0156 (12)	0.0075 (15)
C9	0.0444 (12)	0.0598 (15)	0.0547 (14)	0.0070 (11)	0.0101 (10)	0.0058 (11)
C10	0.0407 (11)	0.0494 (13)	0.0459 (13)	0.0014 (10)	0.0053 (9)	0.0045 (10)
C11	0.0501 (13)	0.0556 (15)	0.0823 (18)	−0.0022 (11)	0.0115 (12)	−0.0008 (13)
C12	0.0718 (18)	0.0572 (17)	0.114 (2)	−0.0058 (14)	0.0102 (16)	−0.0108 (16)
C13	0.091 (2)	0.0591 (17)	0.103 (2)	0.0171 (16)	0.0165 (18)	−0.0126 (16)
C14	0.0645 (16)	0.0731 (18)	0.0809 (19)	0.0219 (14)	0.0223 (14)	0.0032 (15)

Geometric parameters (Å, º) top

N1—C1	1.332 (2)	C6—H6	0.9300
N1—C5	1.427 (2)	C7—C8	1.346 (3)
N1—H1	0.8600	C7—H7	0.9300
O1—C1	1.226 (2)	C8—C9	1.403 (3)
O2—C3	1.208 (2)	C8—H8	0.9300
C1—C2	1.504 (3)	C9—C14	1.410 (3)
C2—C3	1.503 (3)	C9—C10	1.422 (3)
C2—H2A	0.9700	C10—C11	1.408 (3)
C2—H2B	0.9700	C11—C12	1.361 (3)
C3—C4	1.490 (3)	C11—H11	0.9300
C4—H4A	0.9600	C12—C13	1.391 (4)
C4—H4B	0.9600	C12—H12	0.9300
C4—H4C	0.9600	C13—C14	1.344 (4)
C5—C6	1.353 (3)	C13—H13	0.9300
C5—C10	1.413 (3)	C14—H14	0.9300
C6—C7	1.398 (3)

C1—N1—C5	123.47 (17)	C7—C6—H6	119.9
C1—N1—H1	118.3	C8—C7—C6	120.8 (2)
C5—N1—H1	118.3	C8—C7—H7	119.6
O1—C1—N1	123.44 (18)	C6—C7—H7	119.6
O1—C1—C2	120.82 (19)	C7—C8—C9	121.0 (2)
N1—C1—C2	115.72 (18)	C7—C8—H8	119.5
C3—C2—C1	112.45 (16)	C9—C8—H8	119.5
C3—C2—H2A	109.1	C8—C9—C14	122.5 (2)
C1—C2—H2A	109.1	C8—C9—C10	118.9 (2)
C3—C2—H2B	109.1	C14—C9—C10	118.6 (2)
C1—C2—H2B	109.1	C11—C10—C5	123.57 (19)
H2A—C2—H2B	107.8	C11—C10—C9	118.3 (2)
O2—C3—C4	122.28 (19)	C5—C10—C9	118.16 (18)
O2—C3—C2	121.29 (18)	C12—C11—C10	121.0 (2)
C4—C3—C2	116.41 (18)	C12—C11—H11	119.5
C3—C4—H4A	109.5	C10—C11—H11	119.5
C3—C4—H4B	109.5	C11—C12—C13	120.4 (2)
H4A—C4—H4B	109.5	C11—C12—H12	119.8
C3—C4—H4C	109.5	C13—C12—H12	119.8
H4A—C4—H4C	109.5	C14—C13—C12	120.5 (3)
H4B—C4—H4C	109.5	C14—C13—H13	119.7
C6—C5—C10	121.01 (19)	C12—C13—H13	119.7
C6—C5—N1	119.7 (2)	C13—C14—C9	121.3 (2)
C10—C5—N1	119.28 (17)	C13—C14—H14	119.4
C5—C6—C7	120.1 (2)	C9—C14—H14	119.4
C5—C6—H6	119.9

C5—N1—C1—O1	−0.2 (3)	N1—C5—C10—C11	4.3 (3)
C5—N1—C1—C2	178.25 (17)	C6—C5—C10—C9	2.0 (3)
O1—C1—C2—C3	90.1 (2)	N1—C5—C10—C9	−176.73 (18)
N1—C1—C2—C3	−88.3 (2)	C8—C9—C10—C11	178.1 (2)
C1—C2—C3—O2	2.6 (3)	C14—C9—C10—C11	−0.6 (3)
C1—C2—C3—C4	−175.97 (18)	C8—C9—C10—C5	−0.9 (3)
C1—N1—C5—C6	79.3 (3)	C14—C9—C10—C5	−179.6 (2)
C1—N1—C5—C10	−101.9 (2)	C5—C10—C11—C12	178.7 (2)
C10—C5—C6—C7	−1.3 (3)	C9—C10—C11—C12	−0.3 (3)
N1—C5—C6—C7	177.5 (2)	C10—C11—C12—C13	0.7 (4)
C5—C6—C7—C8	−0.7 (4)	C11—C12—C13—C14	−0.1 (5)
C6—C7—C8—C9	1.8 (4)	C12—C13—C14—C9	−0.8 (4)
C7—C8—C9—C14	177.7 (2)	C8—C9—C14—C13	−177.4 (3)
C7—C8—C9—C10	−0.9 (4)	C10—C9—C14—C13	1.2 (4)
C6—C5—C10—C11	−176.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.01	2.853 (2)	168

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₂
M_r	227.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	17.856 (2), 8.1076 (12), 8.5153 (14)
β (°)	102.777 (2)
V (Å³)	1202.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.40 × 0.38

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.959, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	5815, 2116, 1335
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.121, 1.05
No. of reflections	2116
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.17

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), 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	2.01	2.853 (2)	168

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

The authors thank the National Natural Science Foundation of China (grant No. 20671073), NingXia Natural Gas Transferring Key Laboratory (grant No. 2004007) and Weifang University for a research grant.

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Huang, L., Wang, K. Z., Huang, C. H., Li, F. Y. & Huang, Y. Y. (2001). J. Mater. Chem. 11, 790–793. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar