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

The title compound, C(23)H(18)O(4), 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 mol-ecules form π-π stacking inter-actions between naphthalene rings of inversion-related mol-ecules, with an inter-planar 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 = 358.37

Triclinic,

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[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.149

S = 1.05

3355 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −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 ▶).

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

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

Supplementary material file. DOI: 10.1107/S1600536811018745/pk2318Isup3.cml

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

C23H18O4	Z = 2
Mr = 358.37	F(000) = 376
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0672P)2 + 0.1681P] where P = (Fo2 + 2Fc2)/3
3355 reflections	(Δ/σ)max < 0.001
245 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.19 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	0.7525 (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)

	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)

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)