(2,7-Dimethoxy-naphthalene-1,8-di-yl)bis-(4-fluoro-benzo-yl)dimethanone.

The title compound, C(26)H(18)F(2)O(4), is a naphthalene derivative in which the two aroyl groups at the 1- and 8-positions (peri positions) are anti to each other. There is an appreciable difference in the dihedral angles between the naphthalene ring system and the two benzene rings [66.88 (7)° and 88.09 (6)°]. In the crystal, weak C-H⋯O inter-actions involving one of the carbonyl groups and an aromatic C-H group ortho to the F atom seem to stabilize the packing of the mol-ecules.

Related literature

Our study on the selective electrophilic aromatic aroylation of 2,7-dimethoxy­naphthalene, has shown peri-aroylnaphthalene compounds to be formed regioselectively with the aid of a suitable acidic mediator, see: (Okamoto & Yonezawa, 2009 ▶). For related structures, see: Nakaema et al. (2007 ▶, 2008 ▶); Mitsui et al. (2009 ▶).

Experimental

Crystal data

C26H18F2O4

M = 432.42

Monoclinic,

a = 9.87444 (18) Å

b = 17.0275 (3) Å

c = 14.9671 (3) Å

β = 126.871 (1)°

V = 2013.19 (7) Å3

Z = 4

Cu Kα radiation

μ = 0.91 mm−1

T = 296 K

0.40 × 0.40 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.713, T max = 0.915

36825 measured reflections

3682 independent reflections

3338 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.095

S = 1.07

3682 reflections

314 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.18 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: ORTEP (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810000486/ds2015sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000486/ds2015Isup2.hkl

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

C26H18F2O4	F(000) = 896
Mr = 432.42	Dx = 1.427 Mg m−3
Monoclinic, P21/c	Melting point: 469 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54187 Å
a = 9.87444 (18) Å	Cell parameters from 33844 reflections
b = 17.0275 (3) Å	θ = 3.7–68.2°
c = 14.9671 (3) Å	µ = 0.91 mm−1
β = 126.871 (1)°	T = 296 K
V = 2013.19 (7) Å3	Platelet, yellow
Z = 4	0.40 × 0.40 × 0.10 mm

Rigaku R-AXIS RAPID diffractometer	3682 independent reflections
Radiation source: fine-focus sealed tube	3338 reflections with I > 2σ(I)
graphite	Rint = 0.030
Detector resolution: 10.00 pixels mm-1	θmax = 68.2°, θmin = 4.5°
ω scans	h = −11→11
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −20→20
Tmin = 0.713, Tmax = 0.915	l = −18→18
36825 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095	w = 1/[σ2(Fo2) + (0.0494P)2 + 0.3061P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3682 reflections	Δρmax = 0.22 e Å−3
314 parameters	Δρmin = −0.18 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: 0.0030 (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
F1	−0.21053 (13)	0.44424 (5)	−0.09780 (9)	0.0824 (3)
F2	0.35965 (13)	0.21569 (6)	0.65179 (7)	0.0878 (3)
O1	−0.24490 (12)	0.16209 (5)	0.15843 (7)	0.0570 (2)
O2	0.09608 (12)	0.18156 (5)	0.15466 (8)	0.0598 (2)
O3	−0.55074 (11)	0.11265 (6)	−0.11168 (8)	0.0634 (3)
O4	0.31918 (12)	0.01602 (6)	0.31605 (8)	0.0684 (3)
C1	−0.26555 (15)	0.08412 (7)	0.02104 (9)	0.0444 (3)
C2	−0.42192 (16)	0.05978 (7)	−0.07141 (10)	0.0503 (3)
C3	−0.44496 (18)	−0.01516 (8)	−0.11871 (11)	0.0587 (3)
H1	−0.5531	−0.0296	−0.1825	0.070*
C4	−0.31155 (19)	−0.06521 (7)	−0.07028 (11)	0.0580 (3)
H2	−0.3237	−0.1170	−0.1017	0.070*
C5	−0.15072 (17)	−0.04486 (7)	0.02702 (10)	0.0501 (3)
C6	−0.01766 (19)	−0.10000 (7)	0.08034 (12)	0.0574 (3)
H3	−0.0389	−0.1520	0.0463	0.067*
C7	0.13559 (18)	−0.08282 (8)	0.17722 (11)	0.0573 (3)
H4	0.2247	−0.1225	0.2143	0.071*
C8	0.16525 (16)	−0.00701 (7)	0.22300 (10)	0.0516 (3)
C9	0.04104 (15)	0.05019 (7)	0.17254 (9)	0.0450 (3)
C10	−0.12396 (15)	0.03188 (7)	0.07386 (9)	0.0438 (3)
C11	−0.25571 (14)	0.16202 (7)	0.07300 (9)	0.0444 (3)
C12	−0.25352 (14)	0.23685 (7)	0.02252 (9)	0.0449 (3)
C13	−0.20106 (18)	0.30478 (8)	0.08654 (11)	0.0559 (3)
H5	−0.1715	0.3006	0.1573	0.068*
C14	−0.1873 (2)	0.37483 (8)	0.04636 (12)	0.0631 (4)
H6	−0.1474	0.4221	0.0902	0.077*
C15	−0.22767 (18)	0.37560 (8)	−0.05889 (12)	0.0592 (3)
C16	−0.28166 (19)	0.31051 (8)	−0.12562 (11)	0.0614 (3)
H7	−0.3057	0.3146	−0.2008	0.086*
C17	−0.29344 (17)	0.24052 (7)	−0.08343 (10)	0.0526 (3)
H8	−0.3335	0.1938	−0.1306	0.059*
C18	0.09933 (14)	0.13262 (7)	0.21535 (10)	0.0461 (3)
C19	0.16719 (14)	0.15291 (7)	0.33199 (10)	0.0459 (3)
C20	0.29027 (17)	0.21100 (8)	0.38710 (12)	0.0576 (3)
H9	0.3323	0.2342	0.3471	0.074*
C21	0.35501 (18)	0.23239 (9)	0.49493 (12)	0.0642 (4)
H10	0.4460	0.2721	0.5367	0.088*
C22	0.29323 (17)	0.19592 (8)	0.54466 (11)	0.0598 (4)
C23	0.17105 (17)	0.13886 (9)	0.49316 (11)	0.0597 (3)
H11	0.1302	0.1174	0.5288	0.071*
C24	0.10868 (16)	0.11671 (8)	0.38576 (10)	0.0527 (3)
H12	0.0217	0.0758	0.3467	0.062*
C25	−0.71784 (19)	0.08920 (13)	−0.20143 (14)	0.0706 (4)
C26	0.4565 (2)	−0.03775 (11)	0.36866 (15)	0.0697 (4)
H13	−0.751 (3)	0.0383 (12)	−0.1820 (16)	0.098 (6)*
H14	−0.786 (3)	0.1326 (12)	−0.2121 (15)	0.088 (6)*
H15	−0.728 (2)	0.0805 (11)	−0.2710 (16)	0.094 (6)*
H16	0.429 (2)	−0.0860 (11)	0.3956 (14)	0.081 (5)*
H17	0.556 (3)	−0.0075 (11)	0.4306 (16)	0.094 (6)*
H18	0.479 (2)	−0.0552 (10)	0.3166 (15)	0.082 (5)*

	U11	U22	U33	U12	U13	U23
F1	0.1025 (7)	0.0541 (5)	0.1006 (7)	0.0052 (4)	0.0663 (6)	0.0177 (4)
F2	0.0833 (6)	0.1105 (8)	0.0550 (5)	−0.0057 (5)	0.0337 (5)	−0.0239 (5)
O1	0.0680 (6)	0.0644 (6)	0.0454 (5)	0.0048 (4)	0.0377 (4)	0.0000 (4)
O2	0.0666 (6)	0.0548 (5)	0.0592 (5)	−0.0018 (4)	0.0384 (5)	0.0083 (4)
O3	0.0468 (5)	0.0667 (6)	0.0569 (5)	−0.0010 (4)	0.0206 (4)	−0.0085 (4)
O4	0.0548 (5)	0.0657 (6)	0.0631 (6)	0.0165 (4)	0.0237 (5)	0.0001 (5)
C1	0.0507 (6)	0.0438 (6)	0.0414 (6)	−0.0025 (5)	0.0291 (5)	−0.0006 (5)
C2	0.0523 (7)	0.0531 (7)	0.0445 (6)	−0.0034 (5)	0.0285 (6)	−0.0011 (5)
C3	0.0631 (8)	0.0568 (7)	0.0490 (7)	−0.0149 (6)	0.0297 (6)	−0.0093 (6)
C4	0.0771 (9)	0.0442 (7)	0.0547 (7)	−0.0094 (6)	0.0406 (7)	−0.0078 (5)
C5	0.0678 (8)	0.0425 (6)	0.0498 (6)	−0.0030 (5)	0.0405 (6)	−0.0011 (5)
C6	0.0821 (9)	0.0425 (6)	0.0613 (8)	0.0044 (6)	0.0503 (8)	0.0006 (6)
C7	0.0729 (9)	0.0493 (7)	0.0589 (8)	0.0160 (6)	0.0444 (7)	0.0089 (6)
C8	0.0579 (7)	0.0525 (7)	0.0489 (6)	0.0078 (6)	0.0345 (6)	0.0051 (5)
C9	0.0527 (7)	0.0435 (6)	0.0443 (6)	0.0026 (5)	0.0321 (5)	0.0020 (5)
C10	0.0548 (7)	0.0418 (6)	0.0416 (6)	−0.0004 (5)	0.0325 (5)	0.0016 (5)
C11	0.0403 (6)	0.0519 (7)	0.0381 (6)	0.0034 (5)	0.0218 (5)	−0.0015 (5)
C12	0.0437 (6)	0.0462 (6)	0.0427 (6)	0.0053 (5)	0.0248 (5)	−0.0016 (5)
C13	0.0647 (8)	0.0530 (7)	0.0477 (7)	0.0040 (6)	0.0325 (6)	−0.0046 (5)
C14	0.0718 (9)	0.0458 (7)	0.0674 (8)	0.0003 (6)	0.0395 (7)	−0.0074 (6)
C15	0.0637 (8)	0.0480 (7)	0.0692 (8)	0.0074 (6)	0.0417 (7)	0.0103 (6)
C16	0.0732 (9)	0.0610 (8)	0.0541 (7)	0.0048 (7)	0.0405 (7)	0.0063 (6)
C17	0.0621 (8)	0.0508 (7)	0.0463 (6)	0.0010 (6)	0.0332 (6)	−0.0035 (5)
C18	0.0426 (6)	0.0462 (6)	0.0491 (6)	0.0034 (5)	0.0272 (5)	0.0038 (5)
C19	0.0427 (6)	0.0425 (6)	0.0486 (6)	0.0023 (5)	0.0253 (5)	0.0003 (5)
C20	0.0559 (7)	0.0527 (7)	0.0665 (8)	−0.0071 (6)	0.0380 (7)	−0.0078 (6)
C21	0.0566 (8)	0.0597 (8)	0.0686 (9)	−0.0104 (6)	0.0334 (7)	−0.0187 (7)
C22	0.0516 (7)	0.0667 (8)	0.0469 (7)	0.0060 (6)	0.0220 (6)	−0.0099 (6)
C23	0.0537 (7)	0.0735 (9)	0.0485 (7)	0.0017 (6)	0.0288 (6)	0.0034 (6)
C24	0.0478 (6)	0.0552 (7)	0.0477 (6)	−0.0050 (5)	0.0246 (5)	0.0001 (5)
C25	0.0494 (8)	0.0904 (12)	0.0578 (9)	−0.0087 (8)	0.0247 (7)	−0.0112 (8)
C26	0.0586 (9)	0.0752 (10)	0.0733 (10)	0.0202 (8)	0.0385 (8)	0.0156 (8)

F1—C15	1.3610 (15)	C12—C13	1.3888 (17)
F2—C22	1.3611 (15)	C13—C14	1.379 (2)
O1—C11	1.2176 (14)	C13—H5	0.9168
O2—C18	1.2188 (14)	C14—C15	1.374 (2)
O3—C2	1.3681 (16)	C14—H6	0.9600
O3—C25	1.4236 (17)	C15—C16	1.368 (2)
O4—C8	1.3651 (16)	C16—C17	1.3859 (19)
O4—C26	1.4197 (17)	C16—H7	1.0036
C1—C2	1.3808 (17)	C17—H8	0.9758
C1—C10	1.4299 (16)	C18—C19	1.4874 (16)
C1—C11	1.5110 (16)	C19—C24	1.3854 (17)
C2—C3	1.4100 (18)	C19—C20	1.3902 (17)
C3—C4	1.357 (2)	C20—C21	1.381 (2)
C3—H1	0.9430	C20—H9	0.9912
C4—C5	1.4099 (19)	C21—C22	1.363 (2)
C4—H2	0.9717	C21—H10	0.9902
C5—C6	1.4094 (18)	C22—C23	1.370 (2)
C5—C10	1.4305 (16)	C23—C24	1.3847 (18)
C6—C7	1.358 (2)	C23—H11	0.9157
C6—H3	0.9791	C24—H12	0.9809
C7—C8	1.4074 (18)	C25—H13	1.03 (2)
C7—H4	0.9755	C25—H14	0.95 (2)
C8—C9	1.3826 (17)	C25—H15	1.00 (2)
C9—C10	1.4302 (17)	C26—H16	1.018 (19)
C9—C18	1.5065 (16)	C26—H17	1.00 (2)
C11—C12	1.4881 (16)	C26—H18	0.975 (19)
C12—C17	1.3869 (16)
C2—O3—C25	118.43 (12)	C13—C14—H6	122.3
C8—O4—C26	119.26 (12)	F1—C15—C16	118.51 (13)
C2—C1—C10	120.12 (11)	F1—C15—C14	118.29 (13)
C2—C1—C11	117.85 (11)	C16—C15—C14	123.19 (12)
C10—C1—C11	121.47 (10)	C15—C16—C17	117.81 (12)
O3—C2—C1	115.41 (11)	C15—C16—H7	119.3
O3—C2—C3	123.16 (11)	C17—C16—H7	122.8
C1—C2—C3	121.42 (12)	C16—C17—C12	121.05 (12)
C4—C3—C2	119.20 (12)	C16—C17—H8	118.7
C4—C3—H1	121.6	C12—C17—H8	120.3
C2—C3—H1	119.2	O2—C18—C19	120.52 (11)
C3—C4—C5	121.88 (12)	O2—C18—C9	119.18 (11)
C3—C4—H2	120.8	C19—C18—C9	120.24 (10)
C5—C4—H2	117.3	C24—C19—C20	119.52 (11)
C6—C5—C4	120.71 (11)	C24—C19—C18	121.83 (11)
C6—C5—C10	119.72 (12)	C20—C19—C18	118.64 (11)
C4—C5—C10	119.55 (12)	C21—C20—C19	120.52 (13)
C7—C6—C5	121.59 (12)	C21—C20—H9	122.1
C7—C6—H3	120.2	C19—C20—H9	117.3
C5—C6—H3	118.2	C22—C21—C20	118.23 (13)
C6—C7—C8	119.37 (12)	C22—C21—H10	120.0
C6—C7—H4	120.4	C20—C21—H10	121.7
C8—C7—H4	120.3	F2—C22—C21	118.26 (13)
O4—C8—C9	115.77 (11)	F2—C22—C23	118.51 (14)
O4—C8—C7	122.63 (11)	C21—C22—C23	123.20 (12)
C9—C8—C7	121.52 (12)	C22—C23—C24	118.31 (13)
C8—C9—C10	119.88 (11)	C22—C23—H11	120.2
C8—C9—C18	115.89 (11)	C24—C23—H11	121.5
C10—C9—C18	123.37 (10)	C23—C24—C19	120.21 (12)
C1—C10—C9	124.44 (10)	C23—C24—H12	120.4
C1—C10—C5	117.74 (11)	C19—C24—H12	119.4
C9—C10—C5	117.78 (11)	O3—C25—H13	110.7 (11)
O1—C11—C12	120.91 (10)	O3—C25—H14	104.1 (11)
O1—C11—C1	118.64 (11)	H13—C25—H14	113.3 (16)
C12—C11—C1	120.42 (9)	O3—C25—H15	111.1 (11)
C17—C12—C13	118.93 (11)	H13—C25—H15	108.7 (15)
C17—C12—C11	122.58 (10)	H14—C25—H15	109.0 (15)
C13—C12—C11	118.41 (10)	O4—C26—H16	110.5 (10)
C14—C13—C12	120.87 (12)	O4—C26—H17	105.2 (11)
C14—C13—H5	121.7	H16—C26—H17	113.2 (15)
C12—C13—H5	117.4	O4—C26—H18	110.6 (10)
C15—C14—C13	118.15 (12)	H16—C26—H18	108.1 (14)
C15—C14—H6	119.6	H17—C26—H18	109.3 (16)
C25—O3—C2—C1	−175.20 (12)	C10—C1—C11—O1	−68.78 (15)
C25—O3—C2—C3	3.86 (19)	C2—C1—C11—C12	−79.42 (14)
C10—C1—C2—O3	176.46 (10)	C10—C1—C11—C12	109.20 (12)
C11—C1—C2—O3	4.95 (16)	O1—C11—C12—C17	−168.99 (12)
C10—C1—C2—C3	−2.62 (18)	C1—C11—C12—C17	13.08 (17)
C11—C1—C2—C3	−174.13 (11)	O1—C11—C12—C13	14.35 (17)
O3—C2—C3—C4	−177.06 (12)	C1—C11—C12—C13	−163.58 (11)
C1—C2—C3—C4	2.0 (2)	C17—C12—C13—C14	−0.5 (2)
C2—C3—C4—C5	0.9 (2)	C11—C12—C13—C14	176.26 (12)
C3—C4—C5—C6	175.24 (12)	C12—C13—C14—C15	0.3 (2)
C3—C4—C5—C10	−2.9 (2)	C13—C14—C15—F1	−178.54 (13)
C4—C5—C6—C7	−176.63 (13)	C13—C14—C15—C16	0.4 (2)
C10—C5—C6—C7	1.52 (19)	F1—C15—C16—C17	178.04 (13)
C5—C6—C7—C8	−3.0 (2)	C14—C15—C16—C17	−0.9 (2)
C26—O4—C8—C9	−176.00 (12)	C15—C16—C17—C12	0.7 (2)
C26—O4—C8—C7	0.9 (2)	C13—C12—C17—C16	0.01 (19)
C6—C7—C8—O4	−175.71 (12)	C11—C12—C17—C16	−176.63 (12)
C6—C7—C8—C9	1.0 (2)	C8—C9—C18—O2	111.97 (13)
O4—C8—C9—C10	179.36 (10)	C10—C9—C18—O2	−57.38 (16)
C7—C8—C9—C10	2.44 (18)	C8—C9—C18—C19	−65.30 (14)
O4—C8—C9—C18	9.61 (16)	C10—C9—C18—C19	125.35 (12)
C7—C8—C9—C18	−167.31 (11)	O2—C18—C19—C24	150.27 (12)
C2—C1—C10—C9	−177.21 (11)	C9—C18—C19—C24	−32.49 (17)
C11—C1—C10—C9	−6.01 (17)	O2—C18—C19—C20	−28.41 (17)
C2—C1—C10—C5	0.53 (16)	C9—C18—C19—C20	148.83 (12)
C11—C1—C10—C5	171.73 (10)	C24—C19—C20—C21	0.4 (2)
C8—C9—C10—C1	173.95 (11)	C18—C19—C20—C21	179.11 (12)
C18—C9—C10—C1	−17.11 (17)	C19—C20—C21—C22	−0.9 (2)
C8—C9—C10—C5	−3.79 (16)	C20—C21—C22—F2	178.54 (12)
C18—C9—C10—C5	165.16 (11)	C20—C21—C22—C23	0.4 (2)
C6—C5—C10—C1	−176.01 (10)	F2—C22—C23—C24	−177.46 (12)
C4—C5—C10—C1	2.16 (16)	C21—C22—C23—C24	0.7 (2)
C6—C5—C10—C9	1.88 (16)	C22—C23—C24—C19	−1.2 (2)
C4—C5—C10—C9	−179.95 (11)	C20—C19—C24—C23	0.70 (19)
C2—C1—C11—O1	102.61 (13)	C18—C19—C24—C23	−177.97 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H7···O1i	1.00	2.54	3.493 (2)	158
C21—H10···O1ii	0.99	2.68	3.636 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H7⋯O1i	1.00	2.54	3.493 (2)	158
C21—H10⋯O1ii	0.99	2.68	3.636 (2)	161

Symmetry codes: (i) ; (ii) .