(Naphthalene-1,4-di-yl)dimethyl dibenzoate.

In the title compound, C(26)H(20)O(4), the complete molecule is generated by a crystallographic 2-fold axis and the naphthalene ring system is planar within 0.05 (4) Å. The dihedral angles between the -COO plane, the benzene ring and naphthalene ring system are 12.83 (3) and 12.93 (1)°, respectively. The -COO plane and the benzene ring are almost coplanar, forming a dihedral angle of 2.59 (8)°.

Related literature

For applications of related naphthalene derivatives, see: Fukuzumi et al. (1994 ▶); Madsen et al. (2002 ▶); Strey & Voss (1998 ▶); Tsukada et al. (1994 ▶).

Experimental

Crystal data

C26H20O4

M = 396.42

Orthorhombic,

a = 3.9919 (6) Å

b = 60.385 (8) Å

c = 16.231 (2) Å

V = 3912.5 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.50 × 0.38 × 0.07 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.957, T max = 0.994

6343 measured reflections

937 independent reflections

822 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.081

S = 1.08

937 reflections

136 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.10 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810008391/om2316sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008391/om2316Isup2.hkl

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

C26H20O4	F(000) = 1664
Mr = 396.42	Dx = 1.346 Mg m−3
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2 d	Cell parameters from 1789 reflections
a = 3.9919 (6) Å	θ = 2.6–25.3°
b = 60.385 (8) Å	µ = 0.09 mm−1
c = 16.231 (2) Å	T = 296 K
V = 3912.5 (9) Å3	Block, colourless
Z = 8	0.50 × 0.38 × 0.07 mm

Bruker APEXII diffractometer	937 independent reflections
Radiation source: fine-focus sealed tube	822 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −4→4
Tmin = 0.957, Tmax = 0.994	k = −72→72
6343 measured reflections	l = −19→19

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0506P)2] where P = (Fo2 + 2Fc2)/3
937 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.10 e Å−3
1 restraint	Δρmin = −0.15 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.1416 (5)	0.16848 (3)	0.65497 (12)	0.0680 (6)
O2	0.4250 (4)	0.19760 (2)	0.60506 (10)	0.0507 (4)
C1	0.2722 (6)	0.17767 (3)	0.59764 (15)	0.0467 (5)
C2	0.2903 (6)	0.16879 (3)	0.51236 (15)	0.0452 (5)
C3	0.1552 (6)	0.14804 (3)	0.49816 (16)	0.0556 (7)
H3	0.0516	0.1404	0.5408	0.067*
C4	0.1746 (8)	0.13876 (4)	0.42042 (17)	0.0652 (8)
H4	0.0881	0.1247	0.4112	0.078*
C5	0.3209 (7)	0.15021 (4)	0.35675 (18)	0.0655 (7)
H5	0.3302	0.1440	0.3044	0.079*
C6	0.4533 (7)	0.17084 (4)	0.37037 (17)	0.0611 (7)
H6	0.5522	0.1786	0.3272	0.073*
C7	0.4407 (7)	0.18018 (4)	0.44775 (16)	0.0522 (6)
H7	0.5328	0.1941	0.4568	0.063*
C8	0.4461 (6)	0.20608 (3)	0.68748 (14)	0.0455 (5)
H8A	0.5784	0.1961	0.7213	0.055*
H8B	0.2236	0.2071	0.7112	0.055*
C9	0.6053 (5)	0.22851 (3)	0.68603 (13)	0.0413 (5)
C10	0.6767 (5)	0.23923 (3)	0.76281 (14)	0.0391 (5)
C11	0.6072 (6)	0.22913 (4)	0.83964 (14)	0.0474 (6)
H11	0.5109	0.2151	0.8405	0.057*
C12	0.6774 (7)	0.23935 (4)	0.91223 (14)	0.0537 (6)
H12	0.6296	0.2323	0.9618	0.064*
C13	0.6778 (6)	0.23930 (4)	0.61428 (14)	0.0468 (6)
H13	0.6314	0.2324	0.5643	0.056*

	U11	U22	U33	U12	U13	U23
O1	0.0943 (15)	0.0554 (11)	0.0542 (11)	−0.0234 (10)	0.0100 (11)	0.0017 (9)
O2	0.0665 (11)	0.0417 (8)	0.0440 (9)	−0.0096 (7)	0.0002 (8)	−0.0032 (7)
C1	0.0565 (14)	0.0351 (10)	0.0486 (13)	−0.0024 (10)	−0.0037 (11)	0.0034 (11)
C2	0.0506 (13)	0.0390 (11)	0.0458 (13)	0.0011 (9)	−0.0074 (10)	0.0022 (10)
C3	0.0679 (17)	0.0407 (12)	0.0582 (17)	−0.0059 (11)	−0.0134 (13)	0.0024 (11)
C4	0.087 (2)	0.0445 (13)	0.0640 (18)	−0.0039 (13)	−0.0223 (15)	−0.0045 (13)
C5	0.084 (2)	0.0592 (15)	0.0538 (15)	0.0109 (14)	−0.0130 (14)	−0.0110 (14)
C6	0.0730 (18)	0.0615 (16)	0.0488 (15)	0.0047 (13)	0.0000 (13)	0.0010 (12)
C7	0.0627 (15)	0.0423 (11)	0.0517 (14)	−0.0017 (11)	−0.0027 (12)	0.0001 (11)
C8	0.0526 (13)	0.0420 (11)	0.0418 (13)	−0.0017 (10)	−0.0006 (11)	−0.0024 (11)
C9	0.0441 (13)	0.0398 (11)	0.0399 (13)	0.0027 (9)	−0.0010 (10)	0.0006 (10)
C10	0.0412 (11)	0.0398 (10)	0.0362 (11)	0.0054 (9)	0.0006 (10)	0.0003 (10)
C11	0.0558 (15)	0.0422 (11)	0.0442 (13)	−0.0007 (10)	0.0014 (12)	0.0053 (11)
C12	0.0667 (17)	0.0573 (14)	0.0371 (13)	0.0034 (11)	0.0039 (12)	0.0064 (10)
C13	0.0598 (14)	0.0445 (11)	0.0362 (12)	−0.0047 (10)	−0.0032 (11)	−0.0040 (10)

O1—C1	1.202 (3)	C7—H7	0.9300
O2—C1	1.354 (3)	C8—C9	1.496 (3)
O2—C8	1.435 (3)	C8—H8A	0.9700
C1—C2	1.486 (3)	C8—H8B	0.9700
C2—C3	1.384 (3)	C9—C13	1.365 (3)
C2—C7	1.390 (3)	C9—C10	1.433 (3)
C3—C4	1.383 (4)	C10—C11	1.416 (3)
C3—H3	0.9300	C10—C10i	1.426 (4)
C4—C5	1.374 (4)	C11—C12	1.359 (3)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.371 (4)	C12—C12i	1.410 (5)
C5—H5	0.9300	C12—H12	0.9300
C6—C7	1.378 (4)	C13—C13i	1.415 (4)
C6—H6	0.9300	C13—H13	0.9300
C1—O2—C8	115.25 (18)	O2—C8—C9	109.48 (18)
O1—C1—O2	122.4 (2)	O2—C8—H8A	109.8
O1—C1—C2	125.1 (2)	C9—C8—H8A	109.8
O2—C1—C2	112.43 (19)	O2—C8—H8B	109.8
C3—C2—C7	119.4 (2)	C9—C8—H8B	109.8
C3—C2—C1	117.6 (2)	H8A—C8—H8B	108.2
C7—C2—C1	123.03 (19)	C13—C9—C10	118.96 (18)
C4—C3—C2	119.8 (2)	C13—C9—C8	122.36 (19)
C4—C3—H3	120.1	C10—C9—C8	118.67 (18)
C2—C3—H3	120.1	C11—C10—C10i	118.26 (12)
C5—C4—C3	120.4 (2)	C11—C10—C9	122.17 (17)
C5—C4—H4	119.8	C10i—C10—C9	119.57 (11)
C3—C4—H4	119.8	C12—C11—C10	121.8 (2)
C6—C5—C4	120.0 (3)	C12—C11—H11	119.1
C6—C5—H5	120.0	C10—C11—H11	119.1
C4—C5—H5	120.0	C11—C12—C12i	119.92 (13)
C5—C6—C7	120.3 (3)	C11—C12—H12	120.0
C5—C6—H6	119.8	C12i—C12—H12	120.0
C7—C6—H6	119.8	C9—C13—C13i	121.47 (12)
C6—C7—C2	120.1 (2)	C9—C13—H13	119.3
C6—C7—H7	120.0	C13i—C13—H13	119.3
C2—C7—H7	120.0
C8—O2—C1—O1	5.3 (3)	C1—C2—C7—C6	179.0 (2)
C8—O2—C1—C2	−174.01 (19)	C1—O2—C8—C9	−177.40 (18)
O1—C1—C2—C3	−2.0 (4)	O2—C8—C9—C13	6.7 (3)
O2—C1—C2—C3	177.2 (2)	O2—C8—C9—C10	−174.77 (18)
O1—C1—C2—C7	179.2 (3)	C13—C9—C10—C11	179.7 (2)
O2—C1—C2—C7	−1.6 (3)	C8—C9—C10—C11	1.2 (3)
C7—C2—C3—C4	0.8 (4)	C13—C9—C10—C10i	−0.4 (3)
C1—C2—C3—C4	−178.1 (2)	C8—C9—C10—C10i	−179.0 (2)
C2—C3—C4—C5	−1.4 (4)	C10i—C10—C11—C12	−0.2 (4)
C3—C4—C5—C6	1.0 (4)	C9—C10—C11—C12	179.7 (2)
C4—C5—C6—C7	0.0 (4)	C10—C11—C12—C12i	0.2 (5)
C5—C6—C7—C2	−0.6 (4)	C10—C9—C13—C13i	0.2 (4)
C3—C2—C7—C6	0.2 (4)	C8—C9—C13—C13i	178.7 (3)