2,7-Bis(4-acetyl-phen-oxy)naphthalene.

The title compound, C(26)H(20)O(4), has an asymmetrical conformation at 193 K. The 4-acetyl-phenyl groups are twisted away from the the naphthalene ring system, with one benzene ring turned towards the 1-position of the naphthalene ring and the other benzene ring turned towards the 6-position. The inter-planar angles between the mean planes of the benzene rings and the naphthalene ring system are 68.71 (6) and 74.01 (6)°. The structure displays C-H⋯O hydrogen bonding and π-π stacking inter-actions [centroid-centroid and interplanar distances are 3.5938 (9) and 3.517 Å, respectively].

Related literature

For related literature, see: Ocak et al. (2004 ▶).

Experimental

Crystal data

C26H20O4

M = 396.42

Triclinic,

a = 5.8691 (2) Å

b = 7.9105 (2) Å

c = 21.4040 (5) Å

α = 90.322 (2)°

β = 95.534 (2)°

γ = 102.283 (2)°

V = 966.11 (5) Å3

Z = 2

Cu Kα radiation

μ = 0.74 mm−1

T = 193 K

0.60 × 0.20 × 0.02 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.792, T max = 0.985

17040 measured reflections

3467 independent reflections

2617 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.125

S = 1.09

3467 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.24 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SIR2004 (Burla, et al, 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808007496/fl2193sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007496/fl2193Isup2.hkl

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

C26H20O4	Z = 2
Mr = 396.42	F000 = 416
Triclinic, P1	Dx = 1.363 Mg m−3
Hall symbol: -P 1	Melting point = 430.2–430.9 K
a = 5.8691 (2) Å	Cu Kα radiation λ = 1.54187 Å
b = 7.9105 (2) Å	Cell parameters from 12820 reflections
c = 21.4040 (5) Å	θ = 4.2–68.2º
α = 90.322 (2)º	µ = 0.74 mm−1
β = 95.534 (2)º	T = 193 K
γ = 102.283 (2)º	Platelet, clear pale purple
V = 966.11 (5) Å3	0.60 × 0.20 × 0.02 mm

Rigaku R-AXIS RAPID diffractometer	3467 independent reflections
Radiation source: rotating anode	2617 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.030
Detector resolution: 10.00 pixels mm-1	θmax = 68.2º
T = 193 K	θmin = 4.2º
ω scans	h = −6→6
Absorption correction: numerical(NUMABS; Higashi, 1999)	k = −9→9
Tmin = 0.792, Tmax = 0.985	l = −25→25
17040 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.125	w = 1/[σ2(Fo2) + (0.0673P)2 + 0.0881P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
3467 reflections	Δρmax = 0.19 e Å−3
273 parameters	Δρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
O1	0.4929 (2)	0.04326 (15)	0.14405 (5)	0.0460 (3)
O2	0.7532 (2)	0.44294 (17)	−0.10302 (6)	0.0578 (4)
O3	−0.3337 (2)	0.45641 (15)	0.28446 (5)	0.0445 (3)
O4	−0.6274 (2)	0.81543 (16)	0.51905 (6)	0.0542 (4)
C1	0.3180 (3)	0.0478 (2)	0.18309 (7)	0.0364 (4)
C2	0.2243 (3)	0.1895 (2)	0.19006 (7)	0.0363 (4)
H2	0.2721	0.2894	0.1661	0.044*
C3	0.0555 (3)	0.18698 (19)	0.23309 (6)	0.0334 (4)
C4	−0.0519 (3)	0.3297 (2)	0.24098 (7)	0.0361 (4)
H4	−0.0100	0.4308	0.2173	0.043*
C5	−0.2151 (3)	0.3208 (2)	0.28259 (7)	0.0376 (4)
C6	−0.2807 (3)	0.1748 (2)	0.31916 (7)	0.0416 (4)
H6	−0.3939	0.1724	0.3482	0.050*
C7	−0.1796 (3)	0.0366 (2)	0.31236 (7)	0.0402 (4)
H7	−0.2233	−0.0622	0.3371	0.048*
C8	−0.0113 (3)	0.03715 (19)	0.26930 (6)	0.0344 (4)
C9	0.0924 (3)	−0.1059 (2)	0.26025 (7)	0.0410 (4)
H9	0.0496	−0.2065	0.2841	0.049*
C10	0.2526 (3)	−0.1022 (2)	0.21793 (7)	0.0407 (4)
H10	0.3194	−0.1997	0.2120	0.049*
C11	0.4961 (3)	0.13361 (19)	0.08868 (7)	0.0361 (4)
C12	0.2975 (3)	0.1256 (2)	0.04757 (7)	0.0402 (4)
H12	0.1489	0.0664	0.0586	0.048*
C13	0.3166 (3)	0.2042 (2)	−0.00971 (7)	0.0395 (4)
H13	0.1800	0.1984	−0.0380	0.047*
C14	0.5327 (3)	0.29172 (18)	−0.02654 (7)	0.0341 (4)
C15	0.7292 (3)	0.3012 (2)	0.01629 (7)	0.0393 (4)
H15	0.8777	0.3623	0.0059	0.047*
C16	0.7120 (3)	0.2230 (2)	0.07376 (7)	0.0392 (4)
H16	0.8473	0.2307	0.1027	0.047*
C17	0.5597 (3)	0.3703 (2)	−0.08936 (7)	0.0403 (4)
C18	0.3482 (3)	0.3545 (2)	−0.13569 (8)	0.0510 (5)
H18A	0.3925	0.4167	−0.1736	0.061*
H18B	0.2301	0.4043	−0.1172	0.061*
H18C	0.2835	0.2321	−0.1466	0.061*
C19	−0.3525 (3)	0.52941 (19)	0.34179 (7)	0.0359 (4)
C20	−0.1817 (3)	0.5418 (2)	0.39204 (7)	0.0404 (4)
H20	−0.0502	0.4910	0.3891	0.049*
C21	−0.2046 (3)	0.6289 (2)	0.44668 (7)	0.0409 (4)
H21	−0.0859	0.6398	0.4808	0.049*
C22	−0.3988 (3)	0.70055 (19)	0.45228 (7)	0.0359 (4)
C23	−0.5678 (3)	0.6862 (2)	0.40098 (7)	0.0408 (4)
H23	−0.7010	0.7351	0.4039	0.049*
C24	−0.5448 (3)	0.6021 (2)	0.34601 (7)	0.0398 (4)
H24	−0.6606	0.5942	0.3113	0.048*
C25	−0.4346 (3)	0.7891 (2)	0.51118 (7)	0.0407 (4)
C26	−0.2330 (3)	0.8422 (3)	0.56052 (8)	0.0545 (5)
H26A	−0.2649	0.9313	0.5884	0.065*
H26B	−0.0902	0.8885	0.5405	0.065*
H26C	−0.2117	0.7415	0.5851	0.065*

	U11	U22	U33	U12	U13	U23
O1	0.0475 (7)	0.0581 (7)	0.0407 (6)	0.0246 (6)	0.0160 (5)	0.0149 (5)
O2	0.0560 (8)	0.0639 (8)	0.0516 (7)	0.0043 (6)	0.0144 (6)	0.0169 (6)
O3	0.0530 (7)	0.0528 (7)	0.0338 (6)	0.0234 (6)	0.0082 (5)	0.0020 (5)
O4	0.0503 (8)	0.0594 (8)	0.0558 (7)	0.0128 (6)	0.0184 (6)	−0.0041 (6)
C1	0.0351 (9)	0.0458 (9)	0.0299 (8)	0.0113 (7)	0.0054 (6)	0.0031 (6)
C2	0.0380 (9)	0.0388 (9)	0.0315 (8)	0.0067 (7)	0.0041 (6)	0.0051 (6)
C3	0.0338 (8)	0.0389 (8)	0.0266 (7)	0.0062 (7)	0.0010 (6)	0.0007 (6)
C4	0.0395 (9)	0.0370 (8)	0.0311 (8)	0.0064 (7)	0.0038 (6)	0.0030 (6)
C5	0.0385 (9)	0.0427 (9)	0.0332 (8)	0.0127 (7)	0.0025 (6)	−0.0026 (6)
C6	0.0407 (10)	0.0492 (10)	0.0352 (8)	0.0070 (8)	0.0117 (7)	0.0014 (7)
C7	0.0418 (10)	0.0405 (9)	0.0364 (8)	0.0029 (7)	0.0073 (7)	0.0050 (7)
C8	0.0338 (9)	0.0388 (8)	0.0294 (7)	0.0054 (7)	0.0024 (6)	0.0014 (6)
C9	0.0466 (10)	0.0372 (9)	0.0383 (8)	0.0063 (7)	0.0058 (7)	0.0059 (7)
C10	0.0464 (10)	0.0401 (9)	0.0386 (9)	0.0151 (7)	0.0063 (7)	0.0032 (7)
C11	0.0411 (9)	0.0378 (8)	0.0328 (8)	0.0136 (7)	0.0087 (7)	0.0033 (6)
C12	0.0335 (9)	0.0448 (9)	0.0413 (9)	0.0034 (7)	0.0099 (7)	0.0014 (7)
C13	0.0352 (9)	0.0461 (9)	0.0363 (8)	0.0075 (7)	0.0021 (7)	−0.0014 (7)
C14	0.0375 (9)	0.0310 (8)	0.0349 (8)	0.0085 (6)	0.0064 (6)	−0.0014 (6)
C15	0.0339 (9)	0.0390 (9)	0.0438 (9)	0.0031 (7)	0.0085 (7)	0.0023 (7)
C16	0.0341 (9)	0.0466 (9)	0.0375 (8)	0.0106 (7)	0.0025 (7)	0.0004 (7)
C17	0.0483 (10)	0.0364 (8)	0.0390 (9)	0.0126 (7)	0.0103 (7)	0.0020 (7)
C18	0.0608 (12)	0.0583 (11)	0.0380 (9)	0.0221 (9)	0.0049 (8)	0.0060 (8)
C19	0.0377 (9)	0.0370 (8)	0.0346 (8)	0.0083 (7)	0.0103 (7)	0.0032 (6)
C20	0.0353 (9)	0.0462 (9)	0.0426 (9)	0.0143 (7)	0.0053 (7)	0.0019 (7)
C21	0.0388 (9)	0.0459 (9)	0.0390 (9)	0.0123 (7)	0.0019 (7)	0.0027 (7)
C22	0.0358 (9)	0.0335 (8)	0.0383 (8)	0.0053 (6)	0.0079 (7)	0.0031 (6)
C23	0.0332 (9)	0.0433 (9)	0.0478 (9)	0.0103 (7)	0.0081 (7)	0.0022 (7)
C24	0.0345 (9)	0.0446 (9)	0.0411 (9)	0.0110 (7)	0.0020 (7)	0.0016 (7)
C25	0.0445 (10)	0.0369 (8)	0.0418 (9)	0.0073 (7)	0.0129 (7)	0.0054 (7)
C26	0.0574 (12)	0.0635 (12)	0.0432 (10)	0.0149 (9)	0.0048 (8)	−0.0075 (8)

O1—C11	1.3871 (17)	C13—C14	1.391 (2)
O1—C1	1.3905 (17)	C13—H13	0.9500
O2—C17	1.2225 (18)	C14—C15	1.391 (2)
O3—C19	1.3772 (17)	C14—C17	1.492 (2)
O3—C5	1.4001 (18)	C15—C16	1.383 (2)
O4—C25	1.2201 (19)	C15—H15	0.9500
C1—C2	1.363 (2)	C16—H16	0.9500
C1—C10	1.408 (2)	C17—C18	1.495 (2)
C2—C3	1.413 (2)	C18—H18A	0.9800
C2—H2	0.9500	C18—H18B	0.9800
C3—C4	1.422 (2)	C18—H18C	0.9800
C3—C8	1.425 (2)	C19—C24	1.381 (2)
C4—C5	1.361 (2)	C19—C20	1.386 (2)
C4—H4	0.9500	C20—C21	1.386 (2)
C5—C6	1.405 (2)	C20—H20	0.9500
C6—C7	1.363 (2)	C21—C22	1.391 (2)
C6—H6	0.9500	C21—H21	0.9500
C7—C8	1.414 (2)	C22—C23	1.394 (2)
C7—H7	0.9500	C22—C25	1.493 (2)
C8—C9	1.415 (2)	C23—C24	1.381 (2)
C9—C10	1.363 (2)	C23—H23	0.9500
C9—H9	0.9500	C24—H24	0.9500
C10—H10	0.9500	C25—C26	1.495 (2)
C11—C16	1.381 (2)	C26—H26A	0.9800
C11—C12	1.381 (2)	C26—H26B	0.9800
C12—C13	1.381 (2)	C26—H26C	0.9800
C12—H12	0.9500
C11—O1—C1	119.52 (12)	C13—C14—C17	122.02 (14)
C19—O3—C5	118.88 (11)	C16—C15—C14	121.10 (14)
C2—C1—O1	123.00 (14)	C16—C15—H15	119.5
C2—C1—C10	121.89 (14)	C14—C15—H15	119.5
O1—C1—C10	115.03 (14)	C11—C16—C15	119.34 (15)
C1—C2—C3	119.57 (14)	C11—C16—H16	120.3
C1—C2—H2	120.2	C15—C16—H16	120.3
C3—C2—H2	120.2	O2—C17—C14	120.20 (15)
C2—C3—C4	121.79 (14)	O2—C17—C18	120.69 (14)
C2—C3—C8	119.44 (14)	C14—C17—C18	119.09 (14)
C4—C3—C8	118.76 (13)	C17—C18—H18A	109.5
C5—C4—C3	119.74 (14)	C17—C18—H18B	109.5
C5—C4—H4	120.1	H18A—C18—H18B	109.5
C3—C4—H4	120.1	C17—C18—H18C	109.5
C4—C5—O3	117.97 (14)	H18A—C18—H18C	109.5
C4—C5—C6	122.15 (15)	H18B—C18—H18C	109.5
O3—C5—C6	119.65 (14)	O3—C19—C24	116.52 (14)
C7—C6—C5	119.04 (14)	O3—C19—C20	122.80 (14)
C7—C6—H6	120.5	C24—C19—C20	120.53 (14)
C5—C6—H6	120.5	C19—C20—C21	119.39 (15)
C6—C7—C8	121.46 (14)	C19—C20—H20	120.3
C6—C7—H7	119.3	C21—C20—H20	120.3
C8—C7—H7	119.3	C20—C21—C22	121.00 (15)
C7—C8—C9	122.66 (14)	C20—C21—H21	119.5
C7—C8—C3	118.84 (14)	C22—C21—H21	119.5
C9—C8—C3	118.50 (14)	C21—C22—C23	118.36 (14)
C10—C9—C8	121.31 (14)	C21—C22—C25	122.64 (15)
C10—C9—H9	119.3	C23—C22—C25	118.98 (14)
C8—C9—H9	119.3	C24—C23—C22	121.06 (15)
C9—C10—C1	119.28 (15)	C24—C23—H23	119.5
C9—C10—H10	120.4	C22—C23—H23	119.5
C1—C10—H10	120.4	C23—C24—C19	119.63 (15)
C16—C11—C12	120.70 (14)	C23—C24—H24	120.2
C16—C11—O1	116.81 (14)	C19—C24—H24	120.2
C12—C11—O1	122.32 (14)	O4—C25—C22	120.09 (15)
C11—C12—C13	119.49 (14)	O4—C25—C26	120.68 (15)
C11—C12—H12	120.3	C22—C25—C26	119.22 (14)
C13—C12—H12	120.3	C25—C26—H26A	109.5
C12—C13—C14	121.00 (15)	C25—C26—H26B	109.5
C12—C13—H13	119.5	H26A—C26—H26B	109.5
C14—C13—H13	119.5	C25—C26—H26C	109.5
C15—C14—C13	118.34 (14)	H26A—C26—H26C	109.5
C15—C14—C17	119.62 (14)	H26B—C26—H26C	109.5
C11—O1—C1—C2	−34.0 (2)	O1—C11—C12—C13	−173.43 (14)
C11—O1—C1—C10	149.36 (14)	C11—C12—C13—C14	−0.2 (2)
O1—C1—C2—C3	−176.78 (13)	C12—C13—C14—C15	−1.2 (2)
C10—C1—C2—C3	−0.4 (2)	C12—C13—C14—C17	176.96 (14)
C1—C2—C3—C4	−178.38 (14)	C13—C14—C15—C16	1.2 (2)
C1—C2—C3—C8	1.0 (2)	C17—C14—C15—C16	−177.04 (14)
C2—C3—C4—C5	179.42 (14)	C12—C11—C16—C15	−1.7 (2)
C8—C3—C4—C5	0.0 (2)	O1—C11—C16—C15	173.65 (13)
C3—C4—C5—O3	−173.71 (12)	C14—C15—C16—C11	0.3 (2)
C3—C4—C5—C6	0.7 (2)	C15—C14—C17—O2	−0.2 (2)
C19—O3—C5—C4	−132.00 (15)	C13—C14—C17—O2	−178.38 (14)
C19—O3—C5—C6	53.40 (19)	C15—C14—C17—C18	178.13 (14)
C4—C5—C6—C7	−0.7 (2)	C13—C14—C17—C18	0.0 (2)
O3—C5—C6—C7	173.69 (14)	C5—O3—C19—C24	−152.32 (14)
C5—C6—C7—C8	−0.2 (2)	C5—O3—C19—C20	32.1 (2)
C6—C7—C8—C9	−178.51 (14)	O3—C19—C20—C21	175.05 (14)
C6—C7—C8—C3	0.9 (2)	C24—C19—C20—C21	−0.4 (2)
C2—C3—C8—C7	179.76 (13)	C19—C20—C21—C22	1.4 (2)
C4—C3—C8—C7	−0.8 (2)	C20—C21—C22—C23	−1.5 (2)
C2—C3—C8—C9	−0.8 (2)	C20—C21—C22—C25	177.50 (14)
C4—C3—C8—C9	178.62 (13)	C21—C22—C23—C24	0.4 (2)
C7—C8—C9—C10	179.34 (14)	C25—C22—C23—C24	−178.56 (14)
C3—C8—C9—C10	−0.1 (2)	C22—C23—C24—C19	0.6 (2)
C8—C9—C10—C1	0.7 (2)	O3—C19—C24—C23	−176.32 (13)
C2—C1—C10—C9	−0.5 (2)	C20—C19—C24—C23	−0.6 (2)
O1—C1—C10—C9	176.16 (13)	C21—C22—C25—O4	−163.64 (15)
C1—O1—C11—C16	137.94 (14)	C23—C22—C25—O4	15.3 (2)
C1—O1—C11—C12	−46.8 (2)	C21—C22—C25—C26	15.4 (2)
C16—C11—C12—C13	1.7 (2)	C23—C22—C25—C26	−165.70 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2i	0.95	2.54	3.448 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2i	0.95	2.54	3.448 (2)	160

Symmetry code: (i) .