Bis(1-benzoyl-7-meth-oxy-naphthalen-2-yl) terephthalate.

The title molecule, C44H30O8, lies about a crystallographic inversion centre located at the centre of the central benzene ring. The benzene rings in the benzoyl and the terephthalate units make dihedral angles of 67.05 (7)° and 57.57 (7)°, respectively, with the naphthalene ring system. There is an intra-molecular C-H⋯O inter-action between the ketonic carbonyl O atom and an H atom on the naphthalene ring system. In the crystal, C-H⋯O inter-action of the benzene ring in the benzoyl group and weak C=O⋯π inter-action [O⋯centroid = 3.375 (2) Å] of the naphthalene ring with the O atom in the ketonic carbonyl group are observed. These inter-actions form layers parallel to the bc plane.

Related literature

For electrophilic aromatic aroylation of the naphthalene core, see: Okamoto & Yonezawa (2009 ▶); Okamoto et al. (2011 ▶). For the structures of closely related compounds, see: Kato et al. (2010 ▶); Nakaema et al. (2008 ▶); Sakamoto et al. (2012 ▶, 2013 ▶).

Experimental

Crystal data

C44H30O8

M = 686.72

Monoclinic,

a = 9.977 (5) Å

b = 14.922 (7) Å

c = 11.709 (6) Å

β = 106.610 (5)°

V = 1670.5 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.16 × 0.13 × 0.03 mm

Data collection

Rigaku Saturn70 diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.985, T max = 0.997

10969 measured reflections

2909 independent reflections

2354 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.122

S = 1.04

2909 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrystalClear (Rigaku, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku, 2010 ▶); software used to prepare material for publication: CrystalStructure.

Click here for additional data file.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813007186/rn2113sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007186/rn2113Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007186/rn2113Isup3.cml

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

C44H30O8	F(000) = 716
Mr = 686.72	Dx = 1.365 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 4873 reflections
a = 9.977 (5) Å	θ = 2.1–31.2°
b = 14.922 (7) Å	µ = 0.09 mm−1
c = 11.709 (6) Å	T = 173 K
β = 106.610 (5)°	Block, colorless
V = 1670.5 (14) Å3	0.16 × 0.13 × 0.03 mm
Z = 2

Rigaku Saturn70 diffractometer	2909 independent reflections
Radiation source: fine-focus sealed tube	2354 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
Detector resolution: 7.314 pixels mm-1	θmax = 25.0°, θmin = 3.3°
ω scans	h = −11→11
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −13→17
Tmin = 0.985, Tmax = 0.997	l = −13→13
10969 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0716P)2 + 0.0599P] where P = (Fo2 + 2Fc2)/3
2909 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.18 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
O1	0.89735 (14)	0.10507 (8)	0.99483 (11)	0.0365 (3)
O2	0.58268 (14)	0.02769 (9)	1.24046 (11)	0.0370 (4)
O3	0.88903 (12)	−0.06534 (8)	0.75583 (10)	0.0274 (3)
O4	0.71518 (13)	−0.10741 (8)	0.59275 (11)	0.0331 (3)
C1	0.78482 (18)	−0.02789 (11)	0.90842 (14)	0.0250 (4)
C2	0.81191 (18)	−0.09200 (11)	0.83329 (15)	0.0268 (4)
C3	0.78049 (19)	−0.18316 (12)	0.83991 (16)	0.0300 (4)
H3	0.8021	−0.2253	0.7870	0.036*
C4	0.71849 (19)	−0.20981 (12)	0.92361 (16)	0.0317 (4)
H4	0.6966	−0.2714	0.9288	0.038*
C5	0.6193 (2)	−0.17586 (12)	1.08887 (16)	0.0323 (4)
H5	0.5964	−0.2373	1.0932	0.039*
C6	0.58792 (19)	−0.11631 (12)	1.16488 (16)	0.0328 (4)
H6	0.5437	−0.1363	1.2221	0.039*
C7	0.62077 (19)	−0.02485 (12)	1.15912 (15)	0.0298 (4)
C8	0.68635 (18)	0.00528 (12)	1.07862 (14)	0.0268 (4)
H8	0.7093	0.0670	1.0768	0.032*
C9	0.72028 (18)	−0.05563 (11)	0.99763 (15)	0.0263 (4)
C10	0.68584 (18)	−0.14785 (11)	1.00309 (15)	0.0286 (4)
C11	0.83238 (18)	0.06688 (11)	0.90305 (15)	0.0273 (4)
C12	0.79951 (18)	0.11478 (11)	0.78599 (15)	0.0272 (4)
C13	0.68449 (19)	0.09267 (11)	0.69170 (16)	0.0295 (4)
H13	0.6248	0.0451	0.7002	0.035*
C14	0.6557 (2)	0.13957 (12)	0.58465 (17)	0.0366 (5)
H14	0.5757	0.1250	0.5208	0.044*
C15	0.7446 (2)	0.20763 (13)	0.57206 (18)	0.0426 (5)
H15	0.7262	0.2393	0.4988	0.051*
C16	0.8603 (2)	0.22994 (13)	0.66549 (19)	0.0425 (5)
H16	0.9210	0.2765	0.6558	0.051*
C17	0.8877 (2)	0.18470 (12)	0.77284 (18)	0.0365 (5)
H17	0.9660	0.2010	0.8374	0.044*
C18	0.6184 (2)	0.12025 (13)	1.24527 (18)	0.0409 (5)
H18A	0.5809	0.1469	1.1661	0.049*
H18B	0.7204	0.1267	1.2711	0.049*
H18C	0.5784	0.1509	1.3020	0.049*
C19	0.82851 (18)	−0.07386 (11)	0.63596 (15)	0.0259 (4)
C20	0.91934 (18)	−0.03603 (11)	0.56745 (15)	0.0256 (4)
C21	0.87490 (19)	−0.04257 (12)	0.44403 (16)	0.0306 (4)
H21	0.7890	−0.0716	0.4059	0.037*
C22	1.04521 (19)	0.00720 (12)	0.62350 (15)	0.0316 (4)
H22	1.0756	0.0122	0.7079	0.038*

	U11	U22	U33	U12	U13	U23
O1	0.0435 (8)	0.0394 (8)	0.0269 (7)	−0.0090 (6)	0.0105 (6)	−0.0069 (6)
O2	0.0448 (8)	0.0425 (8)	0.0294 (7)	0.0008 (6)	0.0198 (6)	−0.0037 (5)
O3	0.0321 (7)	0.0316 (7)	0.0211 (6)	−0.0011 (5)	0.0120 (5)	−0.0004 (5)
O4	0.0366 (8)	0.0359 (7)	0.0287 (7)	−0.0071 (6)	0.0124 (6)	−0.0030 (5)
C1	0.0281 (9)	0.0274 (9)	0.0202 (9)	0.0003 (7)	0.0080 (7)	0.0017 (7)
C2	0.0286 (9)	0.0326 (10)	0.0206 (9)	0.0002 (7)	0.0092 (7)	0.0035 (7)
C3	0.0372 (10)	0.0271 (10)	0.0281 (10)	0.0013 (7)	0.0130 (8)	−0.0007 (7)
C4	0.0399 (11)	0.0252 (9)	0.0319 (10)	0.0005 (8)	0.0133 (8)	0.0024 (7)
C5	0.0364 (10)	0.0310 (10)	0.0311 (10)	0.0000 (8)	0.0122 (8)	0.0063 (8)
C6	0.0346 (10)	0.0403 (11)	0.0267 (10)	0.0005 (8)	0.0140 (8)	0.0073 (8)
C7	0.0298 (10)	0.0399 (11)	0.0211 (9)	0.0052 (8)	0.0097 (7)	0.0006 (7)
C8	0.0291 (9)	0.0303 (9)	0.0213 (9)	0.0016 (7)	0.0074 (7)	0.0012 (7)
C9	0.0268 (9)	0.0304 (10)	0.0211 (9)	0.0016 (7)	0.0059 (7)	0.0036 (7)
C10	0.0307 (10)	0.0301 (10)	0.0253 (9)	0.0000 (7)	0.0086 (8)	0.0046 (7)
C11	0.0283 (9)	0.0301 (10)	0.0262 (9)	−0.0003 (7)	0.0125 (8)	−0.0014 (7)
C12	0.0316 (10)	0.0254 (9)	0.0275 (10)	0.0023 (7)	0.0131 (8)	0.0004 (7)
C13	0.0327 (10)	0.0269 (9)	0.0314 (10)	0.0016 (7)	0.0134 (8)	0.0002 (7)
C14	0.0411 (11)	0.0342 (11)	0.0329 (11)	0.0030 (9)	0.0079 (9)	0.0040 (8)
C15	0.0561 (13)	0.0356 (11)	0.0366 (12)	0.0030 (10)	0.0143 (10)	0.0131 (8)
C16	0.0475 (12)	0.0329 (11)	0.0503 (13)	−0.0046 (9)	0.0191 (10)	0.0111 (9)
C17	0.0382 (11)	0.0331 (10)	0.0395 (11)	−0.0045 (8)	0.0131 (9)	0.0029 (8)
C18	0.0505 (13)	0.0428 (12)	0.0333 (11)	0.0048 (9)	0.0182 (10)	−0.0040 (8)
C19	0.0325 (10)	0.0227 (9)	0.0240 (9)	0.0024 (7)	0.0105 (8)	−0.0018 (7)
C20	0.0300 (9)	0.0240 (9)	0.0253 (9)	0.0027 (7)	0.0121 (7)	0.0007 (7)
C21	0.0307 (10)	0.0370 (10)	0.0261 (10)	−0.0051 (8)	0.0110 (8)	−0.0023 (7)
C22	0.0366 (10)	0.0392 (10)	0.0190 (9)	−0.0029 (8)	0.0078 (8)	−0.0016 (8)

O1—C11	1.225 (2)	C11—C12	1.497 (2)
O2—C7	1.369 (2)	C12—C13	1.386 (3)
O2—C18	1.423 (2)	C12—C17	1.401 (3)
O3—C19	1.366 (2)	C13—C14	1.392 (3)
O3—C2	1.404 (2)	C13—H13	0.9500
O4—C19	1.208 (2)	C14—C15	1.384 (3)
C1—C2	1.378 (2)	C14—H14	0.9500
C1—C9	1.436 (2)	C15—C16	1.385 (3)
C1—C11	1.499 (2)	C15—H15	0.9500
C2—C3	1.403 (3)	C16—C17	1.383 (3)
C3—C4	1.359 (2)	C16—H16	0.9500
C3—H3	0.9500	C17—H17	0.9500
C4—C10	1.414 (3)	C18—H18A	0.9800
C4—H4	0.9500	C18—H18B	0.9800
C5—C6	1.356 (3)	C18—H18C	0.9800
C5—C10	1.416 (2)	C19—C20	1.483 (2)
C5—H5	0.9500	C20—C21	1.389 (3)
C6—C7	1.410 (3)	C20—C22	1.397 (3)
C6—H6	0.9500	C21—C22i	1.378 (3)
C7—C8	1.368 (2)	C21—H21	0.9500
C8—C9	1.422 (2)	C22—C21i	1.378 (3)
C8—H8	0.9500	C22—H22	0.9500
C9—C10	1.424 (3)
C7—O2—C18	117.86 (14)	C13—C12—C11	122.05 (16)
C19—O3—C2	118.32 (13)	C17—C12—C11	118.43 (16)
C2—C1—C9	118.35 (15)	C12—C13—C14	120.55 (17)
C2—C1—C11	120.41 (15)	C12—C13—H13	119.7
C9—C1—C11	121.05 (15)	C14—C13—H13	119.7
C1—C2—C3	123.39 (16)	C15—C14—C13	119.44 (18)
C1—C2—O3	117.35 (15)	C15—C14—H14	120.3
C3—C2—O3	118.86 (15)	C13—C14—H14	120.3
C4—C3—C2	118.58 (16)	C14—C15—C16	120.47 (18)
C4—C3—H3	120.7	C14—C15—H15	119.8
C2—C3—H3	120.7	C16—C15—H15	119.8
C3—C4—C10	121.40 (17)	C17—C16—C15	120.28 (19)
C3—C4—H4	119.3	C17—C16—H16	119.9
C10—C4—H4	119.3	C15—C16—H16	119.9
C6—C5—C10	121.01 (17)	C16—C17—C12	119.72 (19)
C6—C5—H5	119.5	C16—C17—H17	120.1
C10—C5—H5	119.5	C12—C17—H17	120.1
C5—C6—C7	120.15 (16)	O2—C18—H18A	109.5
C5—C6—H6	119.9	O2—C18—H18B	109.5
C7—C6—H6	119.9	H18A—C18—H18B	109.5
O2—C7—C8	125.02 (17)	O2—C18—H18C	109.5
O2—C7—C6	114.00 (15)	H18A—C18—H18C	109.5
C8—C7—C6	120.98 (16)	H18B—C18—H18C	109.5
C7—C8—C9	120.07 (17)	O4—C19—O3	123.71 (16)
C7—C8—H8	120.0	O4—C19—C20	125.10 (16)
C9—C8—H8	120.0	O3—C19—C20	111.19 (14)
C8—C9—C10	118.76 (15)	C21—C20—C22	119.86 (16)
C8—C9—C1	122.84 (16)	C21—C20—C19	118.26 (16)
C10—C9—C1	118.38 (15)	C22—C20—C19	121.86 (16)
C4—C10—C5	121.11 (16)	C22i—C21—C20	120.34 (17)
C4—C10—C9	119.88 (16)	C22i—C21—H21	119.8
C5—C10—C9	119.02 (16)	C20—C21—H21	119.8
O1—C11—C12	120.23 (16)	C21i—C22—C20	119.80 (17)
O1—C11—C1	119.77 (16)	C21i—C22—H22	120.1
C12—C11—C1	120.00 (15)	C20—C22—H22	120.1
C13—C12—C17	119.52 (17)
C9—C1—C2—C3	−0.4 (3)	C8—C9—C10—C5	−0.1 (2)
C11—C1—C2—C3	174.71 (16)	C1—C9—C10—C5	−178.62 (16)
C9—C1—C2—O3	−173.00 (14)	C2—C1—C11—O1	−129.92 (19)
C11—C1—C2—O3	2.1 (2)	C9—C1—C11—O1	45.1 (2)
C19—O3—C2—C1	−120.17 (17)	C2—C1—C11—C12	50.6 (2)
C19—O3—C2—C3	66.9 (2)	C9—C1—C11—C12	−134.45 (17)
C1—C2—C3—C4	0.9 (3)	O1—C11—C12—C13	−152.96 (17)
O3—C2—C3—C4	173.35 (16)	C1—C11—C12—C13	26.6 (2)
C2—C3—C4—C10	−0.1 (3)	O1—C11—C12—C17	26.3 (2)
C10—C5—C6—C7	0.3 (3)	C1—C11—C12—C17	−154.14 (16)
C18—O2—C7—C8	−2.5 (3)	C17—C12—C13—C14	−0.3 (3)
C18—O2—C7—C6	176.79 (16)	C11—C12—C13—C14	178.96 (16)
C5—C6—C7—O2	179.69 (17)	C12—C13—C14—C15	1.2 (3)
C5—C6—C7—C8	−1.0 (3)	C13—C14—C15—C16	−0.9 (3)
O2—C7—C8—C9	−179.64 (16)	C14—C15—C16—C17	−0.4 (3)
C6—C7—C8—C9	1.1 (3)	C15—C16—C17—C12	1.3 (3)
C7—C8—C9—C10	−0.6 (2)	C13—C12—C17—C16	−1.0 (3)
C7—C8—C9—C1	177.87 (16)	C11—C12—C17—C16	179.72 (17)
C2—C1—C9—C8	−179.22 (16)	C2—O3—C19—O4	−4.1 (2)
C11—C1—C9—C8	5.7 (3)	C2—O3—C19—C20	175.43 (13)
C2—C1—C9—C10	−0.8 (2)	O4—C19—C20—C21	−2.9 (3)
C11—C1—C9—C10	−175.87 (15)	O3—C19—C20—C21	177.60 (14)
C3—C4—C10—C5	179.04 (17)	O4—C19—C20—C22	175.60 (17)
C3—C4—C10—C9	−1.1 (3)	O3—C19—C20—C22	−3.9 (2)
C6—C5—C10—C4	−179.90 (17)	C22—C20—C21—C22i	0.5 (3)
C6—C5—C10—C9	0.2 (3)	C19—C20—C21—C22i	179.03 (16)
C8—C9—C10—C4	−179.97 (16)	C21—C20—C22—C21i	−0.5 (3)
C1—C9—C10—C4	1.5 (2)	C19—C20—C22—C21i	−178.97 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1	0.95	2.41	2.965 (3)	117
C16—H16···O1ii	0.95	2.55	3.258 (3)	132
C22—H22···O3	0.95	2.39	2.717 (3)	100

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1	0.95	2.41	2.965 (3)	117
C16—H16⋯O1i	0.95	2.55	3.258 (3)	132

Symmetry code: (i) .