1,8-Dibenzoyl-2,7-dimethoxy­naphthalene

Nakaema, K.; Watanabe, S.; Okamoto, A.; Noguchi, K.; Yonezawa, N.

doi:10.1107/S1600536808007009

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o807

doi:10.1107/S1600536808007009

Open

access

1,8-Dibenzoyl-2,7-dimethoxynaphthalene

Kosuke Nakaema,^a Shoji Watanabe,^a Akiko Okamoto,^a Keiichi Noguchi ^b and Noriyuki Yonezawa ^a ^*

^aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, Koganei, Tokyo 184-8588, Japan, and ^bInstrumentation Analysis Center, Tokyo University of Agriculture & Technology, Koganei, Tokyo 184-8588, Japan
^*Correspondence e-mail: yonezawa@cc.tuat.ac.jp

(Received 10 March 2008; accepted 13 March 2008; online 4 April 2008)

The molecule of the title compound, C₂₆H₂₀O₄, is located on a twofold rotation axis. The two benzoyl groups are situated in an anti orientation. The dihedral angle between the mean planes of the phenyl ring and the naphthalene ring system is 80.25 (6)°. The phenyl and carbonyl groups in each benzoyl group are almost coplanar. The molecular packing is stabilized by weak C—H⋯O hydrogen bonds and a π–π stacking interaction between the phenyl rings [centroid–centroid and interplanar distances of 3.6383 (10) and 3.294 Å, respectively].

Related literature

For related literature, see: Cohen et al. (2004 ); Gore & Henrick (1980 ); Nakaema et al. (2007 ).

Experimental

Crystal data

C₂₆H₂₀O₄
M_r = 396.42
Monoclinic, C 2/c
a = 13.9677 (4) Å
b = 10.2145 (3) Å
c = 14.6966 (4) Å
β = 109.711 (2)°
V = 1973.95 (10) Å³
Z = 4
Cu Kα radiation
μ = 0.72 mm⁻¹
T = 93 (2) K
0.50 × 0.10 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ) T_min = 0.838, T_max = 0.930
17362 measured reflections
1807 independent reflections
1461 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.115
S = 1.08
1807 reflections
139 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1ⁱ	0.95	2.60	3.4987 (19)	159
C14—H14B⋯O1ⁱⁱ	0.98	2.39	3.344 (2)	164
Symmetry codes: (i) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808007009/is2282sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808007009/is2282Isup2.hkl

checkCIF report

Comment top

The molecules with naphthalene frame, especially, peri-substituted naphthalenes, have received much attention as unique structured aromatic core compounds for variety of the functional materials. Therefore, structural analyses of peri-substituted naphthalenes have been actively performed (Cohen et al., 2004; Gore & Henrick, 1980). Recently, we have reported the structure of 1,8-bis(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Nakaema et al., 2007). In this paper, the crystallographical structural characteristics of a 1,8-diphenylated naphthalene derivative having two methoxy groups at the 2,7-positions are described as the most simple homolog of the previously reported compound. The title compound was successfully synthesized by regioselective electrophilic aromatic substitution reaction of 2,7-dimethoxynaphthalene with benzoic acid.

ORTEPIII (Burnett & Johnson, 1996) plot of title compound is displayed in Fig. 1. The molecule of (I) lies across a crystallographic 2-fold axis so that the asymmetric unit contains one-half of the molecules. Thus, the two benzoyl groups are situated in anti orientation. The benzoyl groups are twisted away from the naphthalene moiety, and the dihedral angle is 80.25 (6)°. The torsion angles between the carbonyl groups and the naphthalene ring are -76.73 (18)° [C6—C1—C7—O1], and those between the carbonyl groups and the phenyl groups are 179.75 (15)° [C13—C8—C7—O1].

In the crystal structure, the molecular packing of (I) is mainly stabilized by van der Waals interaction. In addition, the packing of the molecule is stabilized by relatively weak C—H···O hydrogen bonding, namely, C12—H12···O1ⁱ [symmetry code: (i) x, -y+1, z + 1/2], C14—H14B···O1ⁱⁱ [symmetry code: (ii) -x+1/2, y - 1/2, -z+1/2], and a π—π stacking interaction. In the packing, the molecules are arranged by C—H···O hydrogen bonding along the c axis of the unit cell, and by a π—π stacking interaction perpendicular the bc plane of the unit cell (Fig. 2).

Related literature top

For related literature, see: Cohen et al. (2004); Gore & Henrick (1980); Nakaema et al. (2007).

Experimental top

The title compound was prepared by electrophilic aromatic diaroylation reaction of 2,7-dimethoxynaphthalene with benzoic acid. White single crystals suitable for X-ray diffraction were obtained by recrystallization from ethanol.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I), with the atom-labeling scheme and displacement ellipsoids drawn at the 50% probability level. The symbol "_2" refers to symmetry code: -x, y, -z+1/2.
	Fig. 2. A partial packing diagram of the title compound, viewed down the b axis. The dashed lines indicate hydrogen bonds (blue dashed lines) and π—π stacking interactions (green dashed lines).

1,8-Dibenzoyl-2,7-dimethoxynaphthalene top

Crystal data top

C₂₆H₂₀O₄	F(000) = 832
M_r = 396.42	D_x = 1.334 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -C 2yc	Cell parameters from 10115 reflections
a = 13.9677 (4) Å	θ = 3.2–68.1°
b = 10.2145 (3) Å	µ = 0.72 mm⁻¹
c = 14.6966 (4) Å	T = 93 K
β = 109.711 (2)°	Needle, colorless
V = 1973.95 (10) Å³	0.50 × 0.10 × 0.10 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	1807 independent reflections
Radiation source: rotating anode	1461 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 10.00 pixels mm^-1	θ_max = 68.2°, θ_min = 5.5°
ω scans	h = −16→16
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −12→12
T_min = 0.838, T_max = 0.930	l = −17→17
17362 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.115	w = 1/[σ²(F_o²) + (0.0579P)² + 0.9602P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
1807 reflections	Δρ_max = 0.19 e Å⁻³
139 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00121 (18)

Crystal data top

C₂₆H₂₀O₄	V = 1973.95 (10) Å³
M_r = 396.42	Z = 4
Monoclinic, C2/c	Cu Kα radiation
a = 13.9677 (4) Å	µ = 0.72 mm⁻¹
b = 10.2145 (3) Å	T = 93 K
c = 14.6966 (4) Å	0.50 × 0.10 × 0.10 mm
β = 109.711 (2)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	1807 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	1461 reflections with I > 2σ(I)
T_min = 0.838, T_max = 0.930	R_int = 0.027
17362 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.08	Δρ_max = 0.19 e Å⁻³
1807 reflections	Δρ_min = −0.21 e Å⁻³
139 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
O1	0.11104 (8)	0.59739 (10)	0.22559 (7)	0.0399 (3)
O2	0.26822 (8)	0.39816 (11)	0.37874 (9)	0.0530 (4)
C1	0.09424 (11)	0.39621 (13)	0.29711 (10)	0.0325 (3)
C2	0.18262 (12)	0.32529 (15)	0.33814 (11)	0.0393 (4)
C3	0.18231 (14)	0.18652 (16)	0.33535 (12)	0.0470 (4)
H3	0.2436	0.1385	0.3626	0.056*
C4	0.09246 (14)	0.12359 (15)	0.29280 (11)	0.0463 (4)
H4	0.0919	0.0306	0.2919	0.056*
C5	0.0000	0.19109 (19)	0.2500	0.0383 (5)
C6	0.0000	0.33146 (18)	0.2500	0.0319 (4)
C7	0.10671 (10)	0.54368 (14)	0.29822 (10)	0.0313 (3)
C8	0.11341 (10)	0.61894 (13)	0.38633 (10)	0.0316 (3)
C9	0.12438 (11)	0.75478 (14)	0.38552 (11)	0.0368 (4)
H9	0.1276	0.7970	0.3291	0.044*
C10	0.13055 (12)	0.82794 (16)	0.46611 (12)	0.0431 (4)
H10	0.1384	0.9203	0.4652	0.052*
C11	0.12535 (12)	0.76686 (17)	0.54845 (12)	0.0448 (4)
H11	0.1296	0.8173	0.6040	0.054*
C12	0.11397 (12)	0.63233 (17)	0.54997 (11)	0.0447 (4)
H12	0.1102	0.5906	0.6064	0.054*
C13	0.10816 (11)	0.55857 (15)	0.46934 (10)	0.0376 (4)
H13	0.1006	0.4662	0.4707	0.045*
C14	0.36309 (13)	0.3343 (2)	0.42144 (14)	0.0592 (5)
H14A	0.4171	0.3999	0.4447	0.071*
H14B	0.3771	0.2783	0.3733	0.071*
H14C	0.3606	0.2805	0.4758	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0505 (6)	0.0371 (6)	0.0351 (6)	−0.0020 (4)	0.0185 (5)	0.0020 (4)
O2	0.0393 (6)	0.0456 (7)	0.0658 (8)	0.0087 (5)	0.0068 (5)	−0.0046 (6)
C1	0.0421 (8)	0.0273 (7)	0.0311 (7)	0.0034 (6)	0.0161 (6)	0.0006 (5)
C2	0.0446 (9)	0.0366 (8)	0.0366 (8)	0.0058 (6)	0.0134 (7)	−0.0009 (6)
C3	0.0591 (10)	0.0375 (9)	0.0442 (9)	0.0160 (7)	0.0170 (8)	0.0021 (7)
C4	0.0708 (12)	0.0281 (8)	0.0428 (9)	0.0076 (7)	0.0227 (8)	0.0014 (6)
C5	0.0583 (13)	0.0268 (10)	0.0342 (11)	0.000	0.0212 (10)	0.000
C6	0.0454 (11)	0.0266 (9)	0.0278 (10)	0.000	0.0177 (9)	0.000
C7	0.0307 (7)	0.0306 (7)	0.0330 (8)	0.0011 (5)	0.0116 (6)	0.0022 (6)
C8	0.0300 (7)	0.0312 (7)	0.0333 (8)	−0.0003 (5)	0.0101 (6)	−0.0011 (6)
C9	0.0415 (8)	0.0320 (7)	0.0367 (8)	0.0012 (6)	0.0130 (6)	0.0018 (6)
C10	0.0453 (9)	0.0353 (8)	0.0478 (10)	0.0000 (6)	0.0143 (7)	−0.0069 (7)
C11	0.0426 (9)	0.0515 (10)	0.0415 (9)	−0.0001 (7)	0.0157 (7)	−0.0136 (7)
C12	0.0493 (9)	0.0534 (10)	0.0356 (9)	−0.0040 (7)	0.0199 (7)	−0.0013 (7)
C13	0.0408 (8)	0.0359 (8)	0.0381 (8)	−0.0025 (6)	0.0159 (6)	0.0013 (6)
C14	0.0465 (10)	0.0653 (11)	0.0578 (11)	0.0221 (9)	0.0070 (8)	−0.0151 (9)

Geometric parameters (Å, º) top

O1—C7	1.2197 (16)	C8—C9	1.396 (2)
O2—C2	1.3633 (19)	C9—C10	1.378 (2)
O2—C14	1.4194 (19)	C9—H9	0.9500
C1—C2	1.382 (2)	C10—C11	1.385 (2)
C1—C6	1.4264 (17)	C10—H10	0.9500
C1—C7	1.5158 (19)	C11—C12	1.384 (2)
C2—C3	1.418 (2)	C11—H11	0.9500
C3—C4	1.360 (2)	C12—C13	1.383 (2)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.4110 (19)	C13—H13	0.9500
C4—H4	0.9500	C14—H14A	0.9800
C5—C6	1.434 (3)	C14—H14B	0.9800
C7—C8	1.4814 (19)	C14—H14C	0.9800
C8—C13	1.3908 (19)

C2—O2—C14	119.52 (13)	C13—C8—C7	122.02 (13)
C2—C1—C6	120.72 (14)	C9—C8—C7	118.88 (13)
C2—C1—C7	115.70 (13)	C10—C9—C8	120.44 (14)
C6—C1—C7	123.36 (13)	C10—C9—H9	119.8
O2—C2—C1	115.29 (13)	C8—C9—H9	119.8
O2—C2—C3	123.51 (14)	C9—C10—C11	120.00 (15)
C1—C2—C3	121.19 (15)	C9—C10—H10	120.0
C4—C3—C2	118.62 (15)	C11—C10—H10	120.0
C4—C3—H3	120.7	C12—C11—C10	120.09 (15)
C2—C3—H3	120.7	C12—C11—H11	120.0
C3—C4—C5	122.54 (15)	C10—C11—H11	120.0
C3—C4—H4	118.7	C13—C12—C11	120.05 (15)
C5—C4—H4	118.7	C13—C12—H12	120.0
C4ⁱ—C5—C4	121.50 (19)	C11—C12—H12	120.0
C4ⁱ—C5—C6	119.25 (10)	C12—C13—C8	120.31 (14)
C4—C5—C6	119.25 (10)	C12—C13—H13	119.8
C1—C6—C1ⁱ	124.75 (17)	C8—C13—H13	119.8
C1—C6—C5	117.62 (9)	O2—C14—H14A	109.5
C1ⁱ—C6—C5	117.62 (9)	O2—C14—H14B	109.5
O1—C7—C8	121.63 (13)	H14A—C14—H14B	109.5
O1—C7—C1	118.49 (12)	O2—C14—H14C	109.5
C8—C7—C1	119.88 (12)	H14A—C14—H14C	109.5
C13—C8—C9	119.10 (13)	H14B—C14—H14C	109.5

C14—O2—C2—C1	−179.05 (14)	C4—C5—C6—C1ⁱ	177.70 (9)
C14—O2—C2—C3	−0.3 (2)	C2—C1—C7—O1	97.99 (16)
C6—C1—C2—O2	178.29 (11)	C6—C1—C7—O1	−76.73 (16)
C7—C1—C2—O2	3.43 (18)	C2—C1—C7—C8	−81.97 (16)
C6—C1—C2—C3	−0.5 (2)	C6—C1—C7—C8	103.32 (14)
C7—C1—C2—C3	−175.33 (14)	O1—C7—C8—C13	179.76 (13)
O2—C2—C3—C4	−179.86 (14)	C1—C7—C8—C13	−0.29 (19)
C1—C2—C3—C4	−1.2 (2)	O1—C7—C8—C9	0.4 (2)
C2—C3—C4—C5	1.1 (2)	C1—C7—C8—C9	−179.69 (12)
C3—C4—C5—C4ⁱ	−179.31 (17)	C13—C8—C9—C10	0.4 (2)
C3—C4—C5—C6	0.69 (17)	C7—C8—C9—C10	179.81 (13)
C2—C1—C6—C1ⁱ	−177.80 (14)	C8—C9—C10—C11	−0.3 (2)
C7—C1—C6—C1ⁱ	−3.35 (9)	C9—C10—C11—C12	0.0 (2)
C2—C1—C6—C5	2.20 (14)	C10—C11—C12—C13	0.2 (2)
C7—C1—C6—C5	176.65 (9)	C11—C12—C13—C8	−0.2 (2)
C4ⁱ—C5—C6—C1	177.70 (9)	C9—C8—C13—C12	−0.1 (2)
C4—C5—C6—C1	−2.30 (9)	C7—C8—C13—C12	−179.53 (13)
C4ⁱ—C5—C6—C1ⁱ	−2.30 (9)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱⁱ	0.95	2.60	3.4987 (19)	159
C14—H14B···O1ⁱⁱⁱ	0.98	2.39	3.344 (2)	164

Symmetry codes: (ii) x, −y+1, z+1/2; (iii) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₀O₄
M_r	396.42
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	93
a, b, c (Å)	13.9677 (4), 10.2145 (3), 14.6966 (4)
β (°)	109.711 (2)
V (Å³)	1973.95 (10)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.72
Crystal size (mm)	0.50 × 0.10 × 0.10

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.838, 0.930
No. of measured, independent and observed [I > 2σ(I)] reflections	17362, 1807, 1461
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.115, 1.08
No. of reflections	1807
No. of parameters	139
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.21

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱ	0.95	2.60	3.4987 (19)	159
C14—H14B···O1ⁱⁱ	0.98	2.39	3.344 (2)	164

Symmetry codes: (i) x, −y+1, z+1/2; (ii) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

This work was partially supported by the Ogasawara Foundation for the Promotion of Science & Engineering, Tokyo, Japan.

References

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Cohen, S., Thirumalaikumar, M., Pogodin, S. & Agranat, I. (2004). Struct. Chem. 15, 339–345. Web of Science CSD CrossRef CAS Google Scholar
Gore, P. H. & Henrick, K. (1980). Acta Cryst. B36, 2462–2465. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan. Google Scholar
Nakaema, K., Okamoto, A., Noguchi, K. & Yonezawa, N. (2007). Acta Cryst. E63, o4120. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar