(E)-Ethyl 2-benzoyl-4-(naphthalen-2-yl)-4-oxobut-2-enoate

Wu, L.; Deng, C.; Yang, Y.

doi:10.1107/S1600536811018745

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1499

doi:10.1107/S1600536811018745

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(E)-Ethyl 2-benzoyl-4-(naphthalen-2-yl)-4-oxobut-2-enoate

Liuming Wu,^a Cong Deng ^a and Yan Yang ^a ^*

^aKey Laboratory of Pesticide and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
^*Correspondence e-mail: wuliuming19870721@126.com

(Received 13 April 2011; accepted 17 May 2011; online 25 May 2011)

The title compound, C₂₃H₁₈O₄, is a 1,4-enedione compound which contains a naphthalene ring and a benzene ring. The dihedral angle between the ring systems is 74.9 (2)°. In the crystal, the molecules form π–π stacking interactions between naphthalene rings of inversion-related molecules, with an interplanar spacing of 3.499 (2) Å.

Related literature

For the preparation of the title compound, see: Gao et al. (2010 ). For related structures, see: Prakash et al. (2005 ); Raj et al. (1996 ).

Experimental

Crystal data

C₂₃H₁₈O₄
M_r = 358.37
Triclinic, $[P \overline 1]$
a = 7.8571 (13) Å
b = 9.6157 (16) Å
c = 13.934 (2) Å
α = 99.364 (3)°
β = 105.094 (3)°
γ = 110.648 (3)°
V = 912.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
5661 measured reflections
3355 independent reflections
2818 reflections with I > 2σ(I)
R_int = 0.065

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.149
S = 1.05
3355 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON, SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018745/pk2318sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811018745/pk2318Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811018745/pk2318Isup3.cml

checkCIF report

Comment top

The 1,4-enedione framework is frequently found in bioactive natural products and medicinal compounds. In addition, by virtue of their multifunctional composition, 1,4-enediones could serve as versatile precursors for heterocycle synthesis, Diels-Alder cycloaddition, as well as many other useful transformations. We report here the crystal structure of the title compound (Fig. 1). The crystal packing exhibits offset π-π stacking interactions.

Related literature top

For the preparation of the title compound, see: Gao et al. (2010). For a related structure, see: Prakash et al. (2005); Raj et al. (1996).

Experimental top

The title compound was synthesized according to the reported literature (Gao et al., 2010). Crystals suitable for X-ray diffraction were grown by slow evaporation of a ethyl acetate-hexane (2:1) solution of the title compound at 293 K.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

Fig. 1. A view of the compound with displacement ellipsoids drawn at the 30% probability level.

(E)-Ethyl 2-benzoyl-4-(naphthalen-2-yl)-4-oxobut-2-enoate top

Crystal data top

C₂₃H₁₈O₄	Z = 2
M_r = 358.37	F(000) = 376
Triclinic, P1	D_x = 1.304 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8571 (13) Å	Cell parameters from 2846 reflections
b = 9.6157 (16) Å	θ = 2.4–27.7°
c = 13.934 (2) Å	µ = 0.09 mm⁻¹
α = 99.364 (3)°	T = 298 K
β = 105.094 (3)°	Block, colorless
γ = 110.648 (3)°	0.16 × 0.12 × 0.10 mm
V = 912.6 (3) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	2818 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.065
Graphite monochromator	θ_max = 25.5°, θ_min = 2.4°
ϕ and ω scans	h = −8→9
5661 measured reflections	k = −11→9
3355 independent reflections	l = −16→16

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0672P)² + 0.1681P] where P = (F_o² + 2F_c²)/3
3355 reflections	(Δ/σ)_max < 0.001
245 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₃H₁₈O₄	γ = 110.648 (3)°
M_r = 358.37	V = 912.6 (3) Å³
Triclinic, P1	Z = 2
a = 7.8571 (13) Å	Mo Kα radiation
b = 9.6157 (16) Å	µ = 0.09 mm⁻¹
c = 13.934 (2) Å	T = 298 K
α = 99.364 (3)°	0.16 × 0.12 × 0.10 mm
β = 105.094 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2818 reflections with I > 2σ(I)
5661 measured reflections	R_int = 0.065
3355 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.05	Δρ_max = 0.18 e Å⁻³
3355 reflections	Δρ_min = −0.19 e Å⁻³
245 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	0.7525 (2)	0.3380 (2)	0.02603 (13)	0.0480 (4)
C2	0.6361 (3)	0.2384 (2)	−0.07533 (14)	0.0594 (5)
H2	0.6065	0.1330	−0.0892	0.071*
C3	0.5681 (3)	0.2958 (2)	−0.15181 (14)	0.0634 (5)
H3	0.4969	0.2295	−0.2183	0.076*
C4	0.6024 (3)	0.4539 (2)	−0.13326 (13)	0.0526 (4)
C5	0.5236 (3)	0.5168 (3)	−0.20967 (15)	0.0644 (5)
H5	0.4507	0.4533	−0.2768	0.077*
C6	0.5524 (3)	0.6673 (3)	−0.18670 (17)	0.0666 (6)
H6	0.4974	0.7056	−0.2377	0.080*
C7	0.6642 (3)	0.7654 (3)	−0.08709 (17)	0.0673 (6)
H7	0.6839	0.8689	−0.0721	0.081*
C8	0.7445 (3)	0.7107 (2)	−0.01181 (15)	0.0602 (5)
H8	0.8192	0.7776	0.0542	0.072*
C9	0.7167 (2)	0.5546 (2)	−0.03195 (13)	0.0479 (4)
C10	0.7908 (3)	0.4926 (2)	0.04557 (13)	0.0486 (4)
H10	0.8677	0.5582	0.1117	0.058*
C11	0.8160 (3)	0.2679 (2)	0.10791 (14)	0.0529 (4)
C12	0.9526 (3)	0.3702 (2)	0.21270 (14)	0.0508 (4)
H12	1.0266	0.4736	0.2201	0.061*
C13	0.9720 (2)	0.31813 (19)	0.29631 (13)	0.0458 (4)
C14	0.8554 (3)	0.1555 (2)	0.29805 (14)	0.0502 (4)
C15	0.9508 (2)	0.04721 (18)	0.29869 (13)	0.0466 (4)
C16	0.9100 (3)	−0.0649 (2)	0.35035 (17)	0.0670 (6)
H16	0.8236	−0.0716	0.3859	0.080*
C17	0.9978 (4)	−0.1679 (3)	0.3492 (2)	0.0811 (7)
H17	0.9701	−0.2430	0.3841	0.097*
C18	1.1244 (4)	−0.1585 (2)	0.29701 (19)	0.0737 (6)
H18	1.1812	−0.2285	0.2954	0.088*
C19	1.1676 (3)	−0.0474 (3)	0.24748 (18)	0.0707 (6)
H19	1.2550	−0.0409	0.2126	0.085*
C20	1.0828 (3)	0.0558 (2)	0.24846 (15)	0.0562 (5)
H20	1.1147	0.1322	0.2149	0.067*
C21	1.1107 (3)	0.4188 (2)	0.40120 (13)	0.0500 (4)
C22	1.3699 (3)	0.6602 (3)	0.49986 (16)	0.0761 (6)
H22A	1.4252	0.6045	0.5412	0.091*
H22B	1.3052	0.7056	0.5372	0.091*
C23	1.5227 (4)	0.7817 (3)	0.4819 (2)	0.0995 (9)
H23A	1.5909	0.7365	0.4485	0.149*
H23B	1.6114	0.8551	0.5470	0.149*
H23C	1.4664	0.8333	0.4386	0.149*
O1	0.7583 (2)	0.12815 (15)	0.09194 (11)	0.0762 (5)
O2	0.6987 (2)	0.12270 (17)	0.30777 (13)	0.0743 (4)
O3	1.1113 (3)	0.37690 (18)	0.47767 (11)	0.0809 (5)
O4	1.23194 (19)	0.55455 (14)	0.40043 (9)	0.0607 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0466 (9)	0.0505 (10)	0.0416 (9)	0.0165 (8)	0.0136 (7)	0.0100 (7)
C2	0.0688 (12)	0.0530 (11)	0.0468 (10)	0.0222 (9)	0.0148 (9)	0.0046 (8)
C3	0.0684 (13)	0.0687 (13)	0.0375 (10)	0.0227 (10)	0.0092 (9)	0.0027 (9)
C4	0.0498 (10)	0.0692 (12)	0.0398 (9)	0.0226 (9)	0.0194 (8)	0.0162 (8)
C5	0.0597 (12)	0.0911 (16)	0.0425 (10)	0.0295 (11)	0.0167 (9)	0.0247 (10)
C6	0.0641 (12)	0.0915 (16)	0.0609 (12)	0.0379 (12)	0.0272 (10)	0.0422 (12)
C7	0.0742 (14)	0.0692 (13)	0.0709 (14)	0.0330 (11)	0.0309 (11)	0.0340 (11)
C8	0.0648 (12)	0.0586 (11)	0.0517 (11)	0.0216 (9)	0.0159 (9)	0.0179 (9)
C9	0.0431 (9)	0.0567 (10)	0.0424 (9)	0.0166 (8)	0.0168 (7)	0.0160 (8)
C10	0.0474 (9)	0.0519 (10)	0.0365 (8)	0.0142 (8)	0.0098 (7)	0.0090 (7)
C11	0.0521 (10)	0.0458 (10)	0.0518 (10)	0.0169 (8)	0.0099 (8)	0.0115 (8)
C12	0.0506 (10)	0.0422 (9)	0.0497 (10)	0.0143 (8)	0.0088 (8)	0.0129 (8)
C13	0.0459 (9)	0.0436 (9)	0.0483 (9)	0.0203 (7)	0.0144 (7)	0.0130 (7)
C14	0.0471 (10)	0.0506 (10)	0.0478 (10)	0.0138 (8)	0.0173 (8)	0.0137 (8)
C15	0.0460 (9)	0.0398 (9)	0.0421 (9)	0.0088 (7)	0.0087 (7)	0.0126 (7)
C16	0.0611 (12)	0.0646 (12)	0.0654 (13)	0.0114 (10)	0.0177 (10)	0.0327 (10)
C17	0.0806 (16)	0.0546 (12)	0.0858 (16)	0.0134 (11)	0.0011 (13)	0.0409 (12)
C18	0.0717 (14)	0.0504 (12)	0.0797 (15)	0.0260 (10)	−0.0012 (12)	0.0122 (11)
C19	0.0788 (15)	0.0704 (14)	0.0694 (13)	0.0409 (12)	0.0239 (11)	0.0163 (11)
C20	0.0666 (12)	0.0527 (10)	0.0564 (11)	0.0274 (9)	0.0244 (9)	0.0224 (9)
C21	0.0552 (10)	0.0496 (10)	0.0468 (10)	0.0230 (8)	0.0165 (8)	0.0164 (8)
C22	0.0786 (15)	0.0692 (14)	0.0457 (11)	0.0092 (12)	0.0082 (10)	−0.0021 (10)
C23	0.0779 (17)	0.0856 (18)	0.0757 (16)	−0.0030 (14)	−0.0046 (13)	0.0066 (13)
O1	0.0878 (11)	0.0466 (8)	0.0652 (9)	0.0192 (7)	−0.0030 (8)	0.0097 (7)
O2	0.0568 (9)	0.0716 (9)	0.0978 (11)	0.0209 (7)	0.0394 (8)	0.0244 (8)
O3	0.1044 (12)	0.0704 (10)	0.0491 (8)	0.0171 (9)	0.0188 (8)	0.0249 (7)
O4	0.0654 (8)	0.0528 (8)	0.0406 (7)	0.0071 (6)	0.0084 (6)	0.0092 (6)

Geometric parameters (Å, º) top

C1—C10	1.373 (2)	C13—C14	1.517 (2)
C1—C2	1.420 (3)	C14—O2	1.208 (2)
C1—C11	1.482 (2)	C14—C15	1.482 (3)
C2—C3	1.352 (3)	C15—C20	1.381 (3)
C2—H2	0.9300	C15—C16	1.383 (3)
C3—C4	1.413 (3)	C16—C17	1.392 (3)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.419 (3)	C17—C18	1.365 (4)
C4—C9	1.421 (3)	C17—H17	0.9300
C5—C6	1.352 (3)	C18—C19	1.356 (3)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.394 (3)	C19—C20	1.377 (3)
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.358 (3)	C20—H20	0.9300
C7—H7	0.9300	C21—O3	1.198 (2)
C8—C9	1.406 (3)	C21—O4	1.321 (2)
C8—H8	0.9300	C22—O4	1.453 (2)
C9—C10	1.410 (2)	C22—C23	1.459 (3)
C10—H10	0.9300	C22—H22A	0.9700
C11—O1	1.217 (2)	C22—H22B	0.9700
C11—C12	1.491 (2)	C23—H23A	0.9600
C12—C13	1.335 (2)	C23—H23B	0.9600
C12—H12	0.9300	C23—H23C	0.9600
C13—C21	1.492 (2)

C10—C1—C2	118.91 (16)	C21—C13—C14	112.15 (14)
C10—C1—C11	122.81 (15)	O2—C14—C15	122.53 (16)
C2—C1—C11	118.14 (16)	O2—C14—C13	120.11 (16)
C3—C2—C1	120.47 (18)	C15—C14—C13	117.05 (15)
C3—C2—H2	119.8	C20—C15—C16	118.37 (18)
C1—C2—H2	119.8	C20—C15—C14	121.17 (15)
C2—C3—C4	121.70 (17)	C16—C15—C14	120.46 (17)
C2—C3—H3	119.2	C15—C16—C17	120.2 (2)
C4—C3—H3	119.2	C15—C16—H16	119.9
C3—C4—C5	123.50 (18)	C17—C16—H16	119.9
C3—C4—C9	118.46 (17)	C18—C17—C16	120.1 (2)
C5—C4—C9	118.00 (18)	C18—C17—H17	120.0
C6—C5—C4	121.28 (19)	C16—C17—H17	120.0
C6—C5—H5	119.4	C19—C18—C17	120.2 (2)
C4—C5—H5	119.4	C19—C18—H18	119.9
C5—C6—C7	120.40 (19)	C17—C18—H18	119.9
C5—C6—H6	119.8	C18—C19—C20	120.4 (2)
C7—C6—H6	119.8	C18—C19—H19	119.8
C8—C7—C6	120.4 (2)	C20—C19—H19	119.8
C8—C7—H7	119.8	C19—C20—C15	120.80 (18)
C6—C7—H7	119.8	C19—C20—H20	119.6
C7—C8—C9	121.17 (19)	C15—C20—H20	119.6
C7—C8—H8	119.4	O3—C21—O4	124.25 (17)
C9—C8—H8	119.4	O3—C21—C13	122.09 (17)
C8—C9—C10	122.55 (16)	O4—C21—C13	113.65 (15)
C8—C9—C4	118.77 (17)	O4—C22—C23	108.74 (19)
C10—C9—C4	118.61 (16)	O4—C22—H22A	109.9
C1—C10—C9	121.80 (16)	C23—C22—H22A	109.9
C1—C10—H10	119.1	O4—C22—H22B	109.9
C9—C10—H10	119.1	C23—C22—H22B	109.9
O1—C11—C1	121.54 (17)	H22A—C22—H22B	108.3
O1—C11—C12	118.93 (16)	C22—C23—H23A	109.5
C1—C11—C12	119.53 (15)	C22—C23—H23B	109.5
C13—C12—C11	122.11 (16)	H23A—C23—H23B	109.5
C13—C12—H12	118.9	C22—C23—H23C	109.5
C11—C12—H12	118.9	H23A—C23—H23C	109.5
C12—C13—C21	122.55 (16)	H23B—C23—H23C	109.5
C12—C13—C14	125.27 (16)	C21—O4—C22	116.98 (15)

C10—C1—C2—C3	1.5 (3)	C11—C12—C13—C21	178.92 (16)
C11—C1—C2—C3	177.41 (18)	C11—C12—C13—C14	−3.1 (3)
C1—C2—C3—C4	−2.8 (3)	C12—C13—C14—O2	−84.9 (2)
C2—C3—C4—C5	−175.90 (18)	C21—C13—C14—O2	93.3 (2)
C2—C3—C4—C9	2.0 (3)	C12—C13—C14—C15	101.4 (2)
C3—C4—C5—C6	176.54 (19)	C21—C13—C14—C15	−80.41 (19)
C9—C4—C5—C6	−1.4 (3)	O2—C14—C15—C20	153.77 (19)
C4—C5—C6—C7	1.2 (3)	C13—C14—C15—C20	−32.7 (2)
C5—C6—C7—C8	−0.4 (3)	O2—C14—C15—C16	−26.5 (3)
C6—C7—C8—C9	−0.3 (3)	C13—C14—C15—C16	147.00 (18)
C7—C8—C9—C10	−177.10 (18)	C20—C15—C16—C17	−1.3 (3)
C7—C8—C9—C4	0.1 (3)	C14—C15—C16—C17	178.96 (18)
C3—C4—C9—C8	−177.29 (18)	C15—C16—C17—C18	−0.1 (3)
C5—C4—C9—C8	0.7 (3)	C16—C17—C18—C19	1.1 (4)
C3—C4—C9—C10	0.0 (2)	C17—C18—C19—C20	−0.7 (3)
C5—C4—C9—C10	178.01 (16)	C18—C19—C20—C15	−0.8 (3)
C2—C1—C10—C9	0.4 (3)	C16—C15—C20—C19	1.7 (3)
C11—C1—C10—C9	−175.22 (16)	C14—C15—C20—C19	−178.54 (18)
C8—C9—C10—C1	176.00 (17)	C12—C13—C21—O3	170.97 (19)
C4—C9—C10—C1	−1.2 (3)	C14—C13—C21—O3	−7.2 (2)
C10—C1—C11—O1	169.80 (19)	C12—C13—C21—O4	−10.2 (2)
C2—C1—C11—O1	−5.9 (3)	C14—C13—C21—O4	171.62 (15)
C10—C1—C11—C12	−9.7 (3)	O3—C21—O4—C22	−2.0 (3)
C2—C1—C11—C12	174.56 (16)	C13—C21—O4—C22	179.16 (16)
O1—C11—C12—C13	−19.2 (3)	C23—C22—O4—C21	164.2 (2)
C1—C11—C12—C13	160.31 (17)

Experimental details

Crystal data
Chemical formula	C₂₃H₁₈O₄
M_r	358.37
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.8571 (13), 9.6157 (16), 13.934 (2)
α, β, γ (°)	99.364 (3), 105.094 (3), 110.648 (3)
V (Å³)	912.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.16 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5661, 3355, 2818
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.149, 1.05
No. of reflections	3355
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.19

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Acknowledgements

The author are grateful to Dr Xiang-Gao Meng for the X-ray data collection.

References

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