(Z)-4-(2-Naphthyl-amino)-pent-3-en-2-one.

The title compound, C(15)H(15)NO, which was synthesized under solvent-free conditions by the reaction of acetoacetone and 2-naphthyl-amine, adopts a Z conformation about the C=C bond. The enamine-ketone fragment is approximately planar [maximum deviation = 0.026 (3) Å] and forms a dihedral angle of 39.78 (3)° with the naphthalene ring system. An intra-molecular N-H⋯O hydrogen bond is observed.

Related literature

For our studies on the synthesis of β-enamino­nes and β-enamino esters, see: Harrad et al. (2010 ▶, 2011 ▶). For related structures, see: Shaheen et al. (2006 ▶); Arıcı et al. (1999 ▶).

Experimental

Crystal data

C15H15NO

M = 225.28

Orthorhombic,

a = 11.2417 (18) Å

b = 8.2532 (10) Å

c = 26.570 (4) Å

V = 2465.2 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.48 × 0.34 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS, Bruker, 2008 ▶) T min = 0.660, T max = 0.746

9535 measured reflections

2221 independent reflections

1179 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.142

S = 0.94

2221 reflections

159 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 ▶) and SCHAKAL97 (Keller, 1997 ▶); software used to prepare material for publication: SHELXL97 and PARST95 (Nardelli, 1995 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811024494/ng5187sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024494/ng5187Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811024494/ng5187Isup3.cml

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

C15H15NO	F(000) = 960
Mr = 225.28	Dx = 1.214 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1094 reflections
a = 11.2417 (18) Å	θ = 3.1–19.4°
b = 8.2532 (10) Å	µ = 0.08 mm−1
c = 26.570 (4) Å	T = 296 K
V = 2465.2 (6) Å3	Plate, colourless
Z = 8	0.48 × 0.34 × 0.12 mm

Bruker APEXII CCD diffractometer	2221 independent reflections
Radiation source: fine-focus sealed tube	1179 reflections with I > 2σ(I)
graphite	Rint = 0.057
ω and φ scans	θmax = 25.3°, θmin = 1.5°
Absorption correction: multi-scan (SADABS, Bruker, 2008)	h = −13→8
Tmin = 0.660, Tmax = 0.746	k = −9→9
9535 measured reflections	l = −31→31

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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0749P)2] where P = (Fo2 + 2Fc2)/3
S = 0.94	(Δ/σ)max < 0.001
2221 reflections	Δρmax = 0.19 e Å−3
159 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (2)

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
O1	0.37331 (17)	0.7158 (2)	0.48799 (6)	0.0702 (6)
N1	0.3060 (2)	0.5679 (2)	0.57214 (7)	0.0544 (6)
H1N	0.359 (2)	0.602 (3)	0.5479 (9)	0.081 (9)*
C1	0.3453 (2)	0.5091 (3)	0.61903 (8)	0.0468 (6)
C2	0.2893 (2)	0.5426 (3)	0.66352 (8)	0.0526 (6)
H2	0.2212	0.6066	0.6633	0.063*
C3	0.3326 (2)	0.4819 (2)	0.70984 (8)	0.0465 (6)
C4	0.2751 (2)	0.5120 (3)	0.75613 (9)	0.0616 (7)
H4	0.2051	0.5722	0.7566	0.074*
C5	0.3207 (3)	0.4541 (3)	0.80021 (9)	0.0713 (8)
H5	0.2816	0.4749	0.8304	0.086*
C6	0.4261 (3)	0.3634 (3)	0.80025 (10)	0.0714 (8)
H6	0.4565	0.3241	0.8304	0.086*
C7	0.4840 (2)	0.3327 (3)	0.75657 (10)	0.0646 (7)
H7	0.5540	0.2727	0.7571	0.077*
C8	0.4395 (2)	0.3907 (2)	0.71006 (8)	0.0489 (6)
C9	0.4972 (2)	0.3633 (3)	0.66390 (9)	0.0573 (7)
H9	0.5681	0.3050	0.6635	0.069*
C10	0.4518 (2)	0.4200 (2)	0.61962 (8)	0.0546 (6)
H10	0.4917	0.3996	0.5896	0.065*
C11	0.0924 (2)	0.5082 (3)	0.58249 (9)	0.0661 (7)
H11A	0.0820	0.5612	0.6143	0.099*
H11B	0.1095	0.3956	0.5879	0.099*
H11C	0.0209	0.5183	0.5630	0.099*
C12	0.1937 (2)	0.5854 (3)	0.55465 (8)	0.0517 (6)
C13	0.1742 (2)	0.6647 (3)	0.50990 (8)	0.0563 (7)
H13	0.0958	0.6769	0.4993	0.068*
C14	0.2644 (3)	0.7286 (3)	0.47888 (9)	0.0574 (7)
C15	0.2277 (3)	0.8137 (3)	0.43102 (9)	0.0835 (9)
H15A	0.2948	0.8702	0.4172	0.125*
H15B	0.1654	0.8897	0.4383	0.125*
H15C	0.1995	0.7353	0.4071	0.125*

	U11	U22	U33	U12	U13	U23
O1	0.0617 (13)	0.0837 (12)	0.0651 (11)	−0.0036 (10)	0.0047 (10)	0.0057 (9)
N1	0.0499 (14)	0.0651 (12)	0.0481 (12)	−0.0006 (11)	0.0026 (12)	0.0017 (10)
C1	0.0438 (15)	0.0486 (12)	0.0481 (15)	0.0001 (11)	0.0000 (11)	−0.0053 (11)
C2	0.0497 (16)	0.0521 (14)	0.0560 (15)	0.0084 (11)	−0.0038 (12)	−0.0073 (11)
C3	0.0450 (15)	0.0457 (12)	0.0488 (14)	−0.0069 (11)	0.0007 (12)	−0.0071 (10)
C4	0.0576 (17)	0.0708 (15)	0.0563 (16)	−0.0027 (13)	0.0031 (14)	−0.0120 (12)
C5	0.076 (2)	0.0848 (19)	0.0529 (17)	−0.0202 (17)	0.0030 (16)	−0.0073 (13)
C6	0.073 (2)	0.0849 (18)	0.0559 (17)	−0.0205 (16)	−0.0149 (16)	0.0106 (14)
C7	0.0530 (16)	0.0665 (15)	0.0742 (18)	−0.0044 (12)	−0.0118 (15)	0.0069 (13)
C8	0.0447 (15)	0.0463 (12)	0.0556 (14)	−0.0030 (11)	−0.0065 (12)	−0.0001 (11)
C9	0.0422 (15)	0.0607 (14)	0.0690 (17)	0.0057 (11)	0.0001 (13)	−0.0026 (13)
C10	0.0479 (16)	0.0594 (14)	0.0563 (15)	−0.0002 (12)	0.0105 (12)	−0.0080 (12)
C11	0.0552 (17)	0.0758 (15)	0.0673 (16)	−0.0156 (14)	0.0013 (13)	−0.0088 (13)
C12	0.0499 (16)	0.0519 (13)	0.0532 (14)	−0.0027 (11)	−0.0009 (13)	−0.0139 (11)
C13	0.0505 (16)	0.0678 (15)	0.0506 (14)	0.0000 (13)	−0.0048 (13)	−0.0079 (12)
C14	0.072 (2)	0.0537 (14)	0.0467 (14)	0.0015 (13)	−0.0084 (15)	−0.0070 (11)
C15	0.110 (3)	0.0807 (19)	0.0595 (16)	−0.0019 (16)	−0.0137 (16)	0.0079 (13)

O1—C14	1.252 (3)	C7—H7	0.9300
N1—C12	1.353 (3)	C8—C9	1.406 (3)
N1—C1	1.408 (3)	C9—C10	1.365 (3)
N1—H1N	0.92 (3)	C9—H9	0.9300
C1—C2	1.368 (3)	C10—H10	0.9300
C1—C10	1.405 (3)	C11—C12	1.500 (3)
C2—C3	1.415 (3)	C11—H11A	0.9600
C2—H2	0.9300	C11—H11B	0.9600
C3—C4	1.412 (3)	C11—H11C	0.9600
C3—C8	1.418 (3)	C12—C13	1.375 (3)
C4—C5	1.365 (3)	C13—C14	1.410 (3)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.401 (4)	C14—C15	1.510 (3)
C5—H5	0.9300	C15—H15A	0.9600
C6—C7	1.354 (3)	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600
C7—C8	1.416 (3)
C12—N1—C1	129.3 (2)	C10—C9—C8	121.6 (2)
C12—N1—H1N	109.5 (16)	C10—C9—H9	119.2
C1—N1—H1N	121.1 (16)	C8—C9—H9	119.2
C2—C1—C10	119.2 (2)	C9—C10—C1	120.5 (2)
C2—C1—N1	123.4 (2)	C9—C10—H10	119.7
C10—C1—N1	117.24 (19)	C1—C10—H10	119.7
C1—C2—C3	121.4 (2)	C12—C11—H11A	109.5
C1—C2—H2	119.3	C12—C11—H11B	109.5
C3—C2—H2	119.3	H11A—C11—H11B	109.5
C4—C3—C2	122.5 (2)	C12—C11—H11C	109.5
C4—C3—C8	118.6 (2)	H11A—C11—H11C	109.5
C2—C3—C8	118.90 (19)	H11B—C11—H11C	109.5
C5—C4—C3	120.9 (2)	N1—C12—C13	119.8 (2)
C5—C4—H4	119.5	N1—C12—C11	119.6 (2)
C3—C4—H4	119.5	C13—C12—C11	120.5 (2)
C4—C5—C6	120.4 (2)	C12—C13—C14	124.7 (2)
C4—C5—H5	119.8	C12—C13—H13	117.7
C6—C5—H5	119.8	C14—C13—H13	117.7
C7—C6—C5	120.3 (2)	O1—C14—C13	124.0 (2)
C7—C6—H6	119.8	O1—C14—C15	118.0 (2)
C5—C6—H6	119.8	C13—C14—C15	118.0 (2)
C6—C7—C8	121.0 (2)	C14—C15—H15A	109.5
C6—C7—H7	119.5	C14—C15—H15B	109.5
C8—C7—H7	119.5	H15A—C15—H15B	109.5
C9—C8—C7	122.9 (2)	C14—C15—H15C	109.5
C9—C8—C3	118.25 (19)	H15A—C15—H15C	109.5
C7—C8—C3	118.8 (2)	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.92 (2)	1.85 (2)	2.657 (2)	144 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1	0.92 (2)	1.85 (2)	2.657 (2)	144 (2)