[2,7-Dieth-oxy-8-(4-fluoro-benzo-yl)naphthalen-1-yl](4-fluoro-phen-yl)methanone.

In the mol-ecule of the title compound, C28H22F2O4, the benzoyl groups are aligned almost anti-parallel and the fluorobenzene rings form a dihedral angle of 14.12 (7)°. The dihedral angles between the 2,7-dieth-oxy-naphthalene ring system and the benzene rings are 70.00 (4) and 67.28 (4)°. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯F hydrogen bonds, forming layers parallel to the ab plane. The layers are further connected by π-π inter-actions [centroid-centroid distances of 3.6115 (10) Å] into a three-dimensional structure.

Related literature

For electrophilic aroylation of naphthalene derivatives, see: Okamoto & Yonezawa (2009 ▶); Okamoto et al. (2011 ▶). For the structures of closely related compounds, see: Nakaema et al. (2008 ▶); Watanabe et al. (2010 ▶), Isogai et al. (2013 ▶).

Experimental

Crystal data

C28H22F2O4

M = 460.46

Monoclinic,

a = 7.8592 (18) Å

b = 21.243 (5) Å

c = 13.941 (3) Å

β = 105.141 (3)°

V = 2246.6 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Saturn70 diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.980, T max = 0.980

14368 measured reflections

3836 independent reflections

3439 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.108

S = 1.00

3836 reflections

309 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: Il Milione (Burla et al., 2007 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813008295/rz5052sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008295/rz5052Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008295/rz5052Isup3.cml

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

C28H22F2O4	F(000) = 960
Mr = 460.46	Dx = 1.361 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2yn	Cell parameters from 7582 reflections
a = 7.8592 (18) Å	θ = 1.8–31.3°
b = 21.243 (5) Å	µ = 0.10 mm−1
c = 13.941 (3) Å	T = 173 K
β = 105.141 (3)°	Block, colorless
V = 2246.6 (9) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Rigaku Saturn70 diffractometer	3836 independent reflections
Radiation source: fine-focus sealed tube	3439 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 7.314 pixels mm-1	θmax = 25.0°, θmin = 2.9°
ω scans	h = −9→9
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −25→24
Tmin = 0.980, Tmax = 0.980	l = −14→16
14368 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0756P)2 + 0.3064P] where P = (Fo2 + 2Fc2)/3
3836 reflections	(Δ/σ)max < 0.001
309 parameters	Δρmax = 0.20 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
F1	−0.20117 (11)	0.21137 (4)	0.11577 (9)	0.0549 (3)
F2	1.12357 (11)	0.23089 (4)	0.40563 (7)	0.0453 (2)
O1	0.52489 (11)	0.33949 (4)	0.12884 (7)	0.0287 (2)
O2	0.39925 (11)	0.37322 (4)	0.32983 (7)	0.0300 (2)
O3	0.19889 (11)	0.41165 (4)	−0.05336 (6)	0.0281 (2)
O4	0.71334 (12)	0.48080 (4)	0.44235 (7)	0.0332 (2)
C1	0.36340 (14)	0.43375 (6)	0.10775 (9)	0.0207 (3)
C2	0.27492 (15)	0.45634 (6)	0.01510 (9)	0.0235 (3)
C3	0.27392 (16)	0.52098 (6)	−0.00825 (9)	0.0261 (3)
H3	0.2124	0.5357	−0.0723	0.031*
C4	0.36247 (16)	0.56209 (6)	0.06242 (10)	0.0269 (3)
H4	0.3626	0.6056	0.0467	0.032*
C5	0.54467 (17)	0.58524 (6)	0.23023 (10)	0.0279 (3)
H5	0.5434	0.6286	0.2131	0.033*
C6	0.63394 (17)	0.56678 (6)	0.32334 (10)	0.0287 (3)
H6	0.6949	0.5968	0.3704	0.034*
C7	0.63480 (16)	0.50247 (6)	0.34901 (9)	0.0257 (3)
C8	0.55115 (15)	0.45756 (5)	0.28119 (9)	0.0216 (3)
C9	0.45706 (14)	0.47612 (5)	0.18297 (9)	0.0208 (3)
C10	0.45389 (15)	0.54162 (6)	0.15839 (9)	0.0240 (3)
C11	0.37995 (15)	0.36319 (5)	0.11976 (8)	0.0210 (3)
C12	0.22361 (15)	0.32380 (5)	0.11927 (9)	0.0220 (3)
C13	0.24445 (17)	0.25880 (6)	0.12850 (11)	0.0324 (3)
H13	0.3575	0.2406	0.1358	0.039*
C14	0.10147 (19)	0.22059 (7)	0.12717 (13)	0.0412 (4)
H14	0.1145	0.1762	0.1331	0.049*
C15	−0.06047 (17)	0.24858 (7)	0.11706 (11)	0.0346 (3)
C16	−0.08619 (16)	0.31241 (6)	0.10869 (10)	0.0305 (3)
H16	−0.1995	0.3303	0.1021	0.037*
C17	0.05794 (16)	0.34984 (6)	0.11013 (9)	0.0260 (3)
H17	0.0437	0.3942	0.1048	0.031*
C18	0.54065 (15)	0.39165 (6)	0.32057 (8)	0.0223 (3)
C19	0.70005 (15)	0.35089 (6)	0.34630 (8)	0.0224 (3)
C20	0.68344 (17)	0.28956 (6)	0.37819 (10)	0.0307 (3)
H20	0.5731	0.2755	0.3859	0.037*
C21	0.82595 (19)	0.24894 (6)	0.39870 (11)	0.0354 (3)
H21	0.8148	0.2070	0.4199	0.042*
C22	0.98441 (17)	0.27100 (6)	0.38757 (10)	0.0306 (3)
C23	1.00746 (17)	0.33129 (6)	0.35714 (10)	0.0312 (3)
H23	1.1189	0.3452	0.3508	0.037*
C24	0.86278 (16)	0.37107 (6)	0.33609 (9)	0.0274 (3)
H24	0.8749	0.4128	0.3143	0.033*
C25	0.06420 (17)	0.43112 (7)	−0.13949 (10)	0.0302 (3)
H25A	0.1171	0.4542	−0.1863	0.036*
H25B	−0.0216	0.4591	−0.1199	0.036*
C26	−0.0255 (2)	0.37232 (7)	−0.18738 (12)	0.0454 (4)
H26A	−0.0673	0.3479	−0.1384	0.055*
H26B	0.0582	0.3470	−0.2121	0.055*
H26C	−0.1259	0.3837	−0.2429	0.055*
C27	0.76537 (19)	0.52558 (7)	0.52180 (10)	0.0344 (3)
H27A	0.6655	0.5536	0.5234	0.041*
H27B	0.8641	0.5518	0.5127	0.041*
C28	0.82134 (19)	0.48859 (8)	0.61620 (10)	0.0383 (3)
H28A	0.8508	0.5175	0.6729	0.046*
H28B	0.9250	0.4632	0.6154	0.046*
H28C	0.7249	0.4609	0.6221	0.046*

	U11	U22	U33	U12	U13	U23
F1	0.0318 (5)	0.0366 (5)	0.0949 (8)	−0.0117 (4)	0.0141 (5)	0.0159 (5)
F2	0.0370 (5)	0.0385 (5)	0.0562 (6)	0.0174 (4)	0.0046 (4)	0.0041 (4)
O1	0.0185 (4)	0.0284 (5)	0.0384 (5)	0.0045 (3)	0.0059 (4)	−0.0015 (4)
O2	0.0231 (5)	0.0318 (5)	0.0367 (5)	−0.0034 (4)	0.0105 (4)	0.0029 (4)
O3	0.0288 (5)	0.0281 (5)	0.0231 (5)	0.0021 (4)	−0.0008 (4)	0.0001 (3)
O4	0.0414 (5)	0.0268 (5)	0.0251 (5)	0.0018 (4)	−0.0025 (4)	−0.0040 (4)
C1	0.0162 (5)	0.0229 (6)	0.0242 (6)	0.0004 (4)	0.0073 (5)	0.0013 (5)
C2	0.0178 (6)	0.0274 (6)	0.0256 (6)	0.0010 (5)	0.0062 (5)	−0.0011 (5)
C3	0.0242 (6)	0.0279 (6)	0.0262 (6)	0.0053 (5)	0.0067 (5)	0.0060 (5)
C4	0.0260 (6)	0.0229 (6)	0.0331 (7)	0.0032 (5)	0.0102 (5)	0.0063 (5)
C5	0.0291 (6)	0.0192 (6)	0.0365 (7)	0.0005 (5)	0.0104 (5)	−0.0005 (5)
C6	0.0283 (6)	0.0227 (6)	0.0341 (7)	−0.0019 (5)	0.0062 (5)	−0.0064 (5)
C7	0.0231 (6)	0.0259 (6)	0.0272 (7)	0.0022 (5)	0.0048 (5)	−0.0014 (5)
C8	0.0181 (5)	0.0210 (6)	0.0260 (6)	0.0017 (5)	0.0062 (5)	−0.0006 (5)
C9	0.0162 (5)	0.0217 (6)	0.0258 (6)	0.0011 (4)	0.0078 (5)	−0.0002 (5)
C10	0.0211 (6)	0.0222 (6)	0.0303 (7)	0.0016 (5)	0.0094 (5)	0.0016 (5)
C11	0.0190 (6)	0.0232 (6)	0.0198 (6)	0.0016 (5)	0.0035 (4)	−0.0014 (5)
C12	0.0216 (6)	0.0218 (6)	0.0207 (6)	0.0009 (5)	0.0024 (4)	0.0004 (4)
C13	0.0253 (6)	0.0258 (7)	0.0447 (8)	0.0046 (5)	0.0066 (6)	0.0056 (6)
C14	0.0355 (8)	0.0223 (7)	0.0637 (10)	−0.0003 (6)	0.0094 (7)	0.0088 (6)
C15	0.0265 (7)	0.0309 (7)	0.0440 (8)	−0.0084 (6)	0.0052 (6)	0.0077 (6)
C16	0.0207 (6)	0.0326 (7)	0.0369 (7)	0.0014 (5)	0.0054 (5)	0.0052 (6)
C17	0.0229 (6)	0.0222 (6)	0.0324 (7)	0.0018 (5)	0.0065 (5)	0.0021 (5)
C18	0.0229 (6)	0.0244 (6)	0.0190 (6)	−0.0019 (5)	0.0044 (5)	−0.0019 (5)
C19	0.0235 (6)	0.0226 (6)	0.0198 (6)	−0.0005 (5)	0.0034 (5)	−0.0001 (5)
C20	0.0293 (7)	0.0288 (7)	0.0347 (7)	−0.0012 (5)	0.0092 (5)	0.0063 (5)
C21	0.0410 (8)	0.0244 (6)	0.0394 (8)	0.0032 (6)	0.0082 (6)	0.0084 (6)
C22	0.0302 (7)	0.0292 (7)	0.0284 (7)	0.0100 (5)	0.0006 (5)	0.0004 (5)
C23	0.0221 (6)	0.0328 (7)	0.0374 (7)	−0.0005 (5)	0.0057 (5)	−0.0011 (6)
C24	0.0255 (6)	0.0225 (6)	0.0333 (7)	−0.0015 (5)	0.0059 (5)	0.0020 (5)
C25	0.0260 (6)	0.0348 (7)	0.0259 (7)	0.0028 (5)	−0.0003 (5)	0.0029 (5)
C26	0.0436 (8)	0.0419 (9)	0.0395 (8)	−0.0017 (7)	−0.0094 (7)	−0.0002 (7)
C27	0.0387 (7)	0.0339 (7)	0.0285 (7)	−0.0037 (6)	0.0049 (6)	−0.0085 (6)
C28	0.0374 (8)	0.0470 (9)	0.0280 (7)	−0.0011 (6)	0.0041 (6)	−0.0037 (6)

F1—C15	1.3555 (15)	C14—C15	1.378 (2)
F2—C22	1.3571 (15)	C14—H14	0.9500
O1—C11	1.2213 (14)	C15—C16	1.371 (2)
O2—C18	1.2165 (15)	C16—C17	1.3799 (18)
O3—C2	1.3680 (15)	C16—H16	0.9500
O3—C25	1.4385 (15)	C17—H17	0.9500
O4—C7	1.3662 (16)	C18—C19	1.4876 (16)
O4—C27	1.4360 (16)	C19—C24	1.3909 (17)
C1—C2	1.3831 (17)	C19—C20	1.3936 (18)
C1—C9	1.4313 (17)	C20—C21	1.3833 (19)
C1—C11	1.5100 (16)	C20—H20	0.9500
C2—C3	1.4107 (17)	C21—C22	1.377 (2)
C3—C4	1.3636 (19)	C21—H21	0.9500
C3—H3	0.9500	C22—C23	1.3760 (19)
C4—C10	1.4118 (18)	C23—C24	1.3852 (18)
C4—H4	0.9500	C23—H23	0.9500
C5—C6	1.3619 (19)	C24—H24	0.9500
C5—C10	1.4132 (18)	C25—C26	1.502 (2)
C5—H5	0.9500	C25—H25A	0.9900
C6—C7	1.4118 (18)	C25—H25B	0.9900
C6—H6	0.9500	C26—H26A	0.9800
C7—C8	1.3826 (17)	C26—H26B	0.9800
C8—C9	1.4311 (17)	C26—H26C	0.9800
C8—C18	1.5140 (16)	C27—C28	1.497 (2)
C9—C10	1.4316 (17)	C27—H27A	0.9900
C11—C12	1.4851 (16)	C27—H27B	0.9900
C12—C17	1.3896 (17)	C28—H28A	0.9800
C12—C13	1.3925 (18)	C28—H28B	0.9800
C13—C14	1.3823 (19)	C28—H28C	0.9800
C13—H13	0.9500
C2—O3—C25	118.36 (10)	C17—C16—H16	121.1
C7—O4—C27	118.57 (10)	C16—C17—C12	121.19 (12)
C2—C1—C9	120.19 (11)	C16—C17—H17	119.4
C2—C1—C11	117.11 (10)	C12—C17—H17	119.4
C9—C1—C11	122.02 (10)	O2—C18—C19	121.48 (11)
O3—C2—C1	115.60 (11)	O2—C18—C8	118.29 (11)
O3—C2—C3	122.64 (11)	C19—C18—C8	120.23 (10)
C1—C2—C3	121.63 (11)	C24—C19—C20	119.08 (11)
C4—C3—C2	119.05 (11)	C24—C19—C18	122.33 (11)
C4—C3—H3	120.5	C20—C19—C18	118.55 (11)
C2—C3—H3	120.5	C21—C20—C19	120.72 (12)
C3—C4—C10	121.66 (12)	C21—C20—H20	119.6
C3—C4—H4	119.2	C19—C20—H20	119.6
C10—C4—H4	119.2	C22—C21—C20	118.15 (12)
C6—C5—C10	121.71 (12)	C22—C21—H21	120.9
C6—C5—H5	119.1	C20—C21—H21	120.9
C10—C5—H5	119.1	F2—C22—C23	118.49 (12)
C5—C6—C7	119.17 (12)	F2—C22—C21	118.31 (12)
C5—C6—H6	120.4	C23—C22—C21	123.19 (12)
C7—C6—H6	120.4	C22—C23—C24	117.79 (12)
O4—C7—C8	115.77 (11)	C22—C23—H23	121.1
O4—C7—C6	122.58 (11)	C24—C23—H23	121.1
C8—C7—C6	121.62 (12)	C23—C24—C19	121.07 (12)
C7—C8—C9	119.92 (11)	C23—C24—H24	119.5
C7—C8—C18	116.83 (11)	C19—C24—H24	119.5
C9—C8—C18	122.57 (10)	O3—C25—C26	106.83 (11)
C8—C9—C1	124.47 (11)	O3—C25—H25A	110.4
C8—C9—C10	117.98 (11)	C26—C25—H25A	110.4
C1—C9—C10	117.54 (11)	O3—C25—H25B	110.4
C4—C10—C5	120.50 (11)	C26—C25—H25B	110.4
C4—C10—C9	119.92 (11)	H25A—C25—H25B	108.6
C5—C10—C9	119.57 (11)	C25—C26—H26A	109.5
O1—C11—C12	121.09 (11)	C25—C26—H26B	109.5
O1—C11—C1	118.14 (10)	H26A—C26—H26B	109.5
C12—C11—C1	120.77 (9)	C25—C26—H26C	109.5
C17—C12—C13	119.21 (11)	H26A—C26—H26C	109.5
C17—C12—C11	122.03 (11)	H26B—C26—H26C	109.5
C13—C12—C11	118.76 (11)	O4—C27—C28	106.82 (12)
C14—C13—C12	120.36 (12)	O4—C27—H27A	110.4
C14—C13—H13	119.8	C28—C27—H27A	110.4
C12—C13—H13	119.8	O4—C27—H27B	110.4
C15—C14—C13	118.29 (13)	C28—C27—H27B	110.4
C15—C14—H14	120.9	H27A—C27—H27B	108.6
C13—C14—H14	120.9	C27—C28—H28A	109.5
F1—C15—C16	118.28 (12)	C27—C28—H28B	109.5
F1—C15—C14	118.57 (12)	H28A—C28—H28B	109.5
C16—C15—C14	123.15 (12)	C27—C28—H28C	109.5
C15—C16—C17	117.80 (12)	H28A—C28—H28C	109.5
C15—C16—H16	121.1	H28B—C28—H28C	109.5
C25—O3—C2—C1	162.02 (10)	C2—C1—C11—C12	−70.49 (14)
C25—O3—C2—C3	−21.99 (16)	C9—C1—C11—C12	118.99 (12)
C9—C1—C2—O3	176.08 (9)	O1—C11—C12—C17	179.27 (11)
C11—C1—C2—O3	5.37 (15)	C1—C11—C12—C17	−1.48 (17)
C9—C1—C2—C3	0.05 (17)	O1—C11—C12—C13	−0.57 (17)
C11—C1—C2—C3	−170.66 (10)	C1—C11—C12—C13	178.68 (11)
O3—C2—C3—C4	−175.76 (11)	C17—C12—C13—C14	0.9 (2)
C1—C2—C3—C4	−0.01 (18)	C11—C12—C13—C14	−179.24 (13)
C2—C3—C4—C10	−0.45 (18)	C12—C13—C14—C15	−0.3 (2)
C10—C5—C6—C7	−0.46 (18)	C13—C14—C15—F1	−179.95 (13)
C27—O4—C7—C8	−165.39 (11)	C13—C14—C15—C16	−0.3 (2)
C27—O4—C7—C6	12.87 (17)	F1—C15—C16—C17	179.97 (12)
C5—C6—C7—O4	−176.44 (11)	C14—C15—C16—C17	0.3 (2)
C5—C6—C7—C8	1.72 (19)	C15—C16—C17—C12	0.31 (19)
O4—C7—C8—C9	176.68 (10)	C13—C12—C17—C16	−0.90 (19)
C6—C7—C8—C9	−1.59 (18)	C11—C12—C17—C16	179.25 (11)
O4—C7—C8—C18	5.96 (16)	C7—C8—C18—O2	106.26 (13)
C6—C7—C8—C18	−172.32 (11)	C9—C8—C18—O2	−64.20 (15)
C7—C8—C9—C1	−178.81 (11)	C7—C8—C18—C19	−74.15 (14)
C18—C8—C9—C1	−8.64 (17)	C9—C8—C18—C19	115.39 (12)
C7—C8—C9—C10	0.23 (16)	O2—C18—C19—C24	179.91 (11)
C18—C8—C9—C10	170.41 (10)	C8—C18—C19—C24	0.33 (17)
C2—C1—C9—C8	179.41 (11)	O2—C18—C19—C20	2.35 (18)
C11—C1—C9—C8	−10.35 (17)	C8—C18—C19—C20	−177.23 (11)
C2—C1—C9—C10	0.36 (16)	C24—C19—C20—C21	−0.56 (19)
C11—C1—C9—C10	170.60 (10)	C18—C19—C20—C21	177.08 (12)
C3—C4—C10—C5	179.97 (11)	C19—C20—C21—C22	0.6 (2)
C3—C4—C10—C9	0.86 (18)	C20—C21—C22—F2	−178.65 (12)
C6—C5—C10—C4	−179.98 (12)	C20—C21—C22—C23	0.0 (2)
C6—C5—C10—C9	−0.87 (18)	F2—C22—C23—C24	178.07 (11)
C8—C9—C10—C4	−179.91 (10)	C21—C22—C23—C24	−0.6 (2)
C1—C9—C10—C4	−0.80 (16)	C22—C23—C24—C19	0.60 (19)
C8—C9—C10—C5	0.97 (16)	C20—C19—C24—C23	−0.05 (19)
C1—C9—C10—C5	−179.92 (10)	C18—C19—C24—C23	−177.59 (11)
C2—C1—C11—O1	108.79 (12)	C2—O3—C25—C26	−166.28 (11)
C9—C1—C11—O1	−61.74 (15)	C7—O4—C27—C28	171.67 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1i	0.95	2.30	3.1939 (17)	156
C23—H23···O2ii	0.95	2.37	3.3214 (18)	176
C6—H6···F1iii	0.95	2.44	3.1937 (17)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O1i	0.95	2.30	3.1939 (17)	156
C23—H23⋯O2ii	0.95	2.37	3.3214 (18)	176
C6—H6⋯F1iii	0.95	2.44	3.1937 (17)	136

Symmetry codes: (i) ; (ii) ; (iii) .