[2,7-Dieth­oxy-8-(4-fluoro­benzo­yl)naphthalen-1-yl](4-fluoro­phen­yl)methanone

Mouri, S.; Hijikata, D.; Isozaki, K.; Yonezawa, N.; Okamoto, A.

doi:10.1107/S1600536813008295

organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page o637

https://doi.org/10.1107/S1600536813008295

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[2,7-Diethoxy-8-(4-fluorobenzoyl)naphthalen-1-yl](4-fluorophenyl)methanone

Saki Mouri,^a Daichi Hijikata,^a Katsuhiro Isozaki,^b Noriyuki Yonezawa ^a and Akiko Okamoto ^a ^*

^aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology (TUAT), Koganei, Tokyo 184-8588, Japan, and ^bInternational Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan
^*Correspondence e-mail: aokamoto@cc.tuat.ac.jp

(Received 15 March 2013; accepted 26 March 2013; online 5 April 2013)

In the molecule of the title compound, C₂₈H₂₂F₂O₄, the benzoyl groups are aligned almost antiparallel and the fluorobenzene rings form a dihedral angle of 14.12 (7)°. The dihedral angles between the 2,7-diethoxynaphthalene ring system and the benzene rings are 70.00 (4) and 67.28 (4)°. In the crystal, molecules 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 interactions [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_r = 460.46
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.036
wR(F²) = 0.108
S = 1.00
3836 reflections
309 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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) x-1, y, z; (ii) x+1, y, z; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813008295/rz5052sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813008295/rz5052Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813008295/rz5052Isup3.cml

checkCIF report

Comment top

In the course of our studies on the selective electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene, peri-aroylnaphthalene compounds have proved to be formed regioselectively with the aid of a suitable acidic mediator (Okamoto & Yonezawa, 2009; Okamoto et al., 2011). The two aroyl groups at the 1,8-positions of the naphthalene ring in the resulting compounds are attached in perpendicular fashion to the naphthalene ring and oriented in opposite direction. Recently, we have reported the X-ray crystal structures of 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema et al., 2008), 1,8-bis(4-fluorobenzoyl)-2,7-dimethoxynaphthalene [(2,7-dimethoxynaphthalene-1,8-diyl)-bis(4-fluorobenzoyl)dimethanone; Watanabe et al., 2010], and 1,8-dibenzoyl-2,7-diethoxynaphthalene [(8-benzoyl-2,7-diethoxynaphthalen-1-yl)-(phenyl)methanone (Isogai et al., 2013). In the crystal of 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema et al., 2008), the molecule lies across a crystallographic twofold axis so that the asymmetric unit contains one-half of the molecule. The dihedral angle between the benzene ring and the naphthalene ring is 83.59 (5)°. In the case of 1,8-dibenzoyl-2,7-diethoxynaphthalene (Isogai et al., 2013), the dihedral angles are 68.42 (5)° and 71.69 (5)°. On the other hand, two aroyl groups in 1,8-bis(4-fluorobenzoyl)-2,7-dimethoxynaphthalene (Watanabe et al., 2010) are attached to the naphthalene ring with appreciably different dihedral angles of 66.88 (7)° and 88.09 (6)°.

In the crystal packing of 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema et al., 2008) and analogous compounds (Watanabe et al., 2010, Isogai et al., 2013), the molecules are linked by C—H···O hydrogen bonds between the benzene rings and the ketonic carbonyl groups forming a three-dimensional network. The distances are shorter in the order of 1,8-dibenzoyl-2,7-dimethoxynaphthalene (2.60 Å), 1,8-bis(4-fluorobenzoyl) analogue (2.55 Å), and the 2,7-diethoxy analogue (2.37 Å).

As a part of our continuous studies on the molecular structures of this kind of homologous molecules, the X-ray crystal structure of the title compound, 1,8-bis(4-fluorobenzoyl)-2,7-diethoxynaphthalene is discussed in this article.

In the molecule (Fig. 1), two aroyl groups are non-coplanarly attached to the naphthalene ring and are oriented in opposite direction. The dihedral angles between the planes of the benzene rings [C12—C17 and C19—C24] and the naphthalene ring system (C1—C10) are 70.00 (4)° and 67.28 (4)°, respectively. Besides, the dihedral angle between the benzene rings is 14.12 (7)°.

The molecular packing of the title compound is mainly stabilized by dual C—H···O hydrogen bonds between the benzene rings and the ketonic carbonyl groups along the a axis (C16—H16···O1ⁱ=2.30 Å and C23—H23···O2ⁱⁱ=2.37 Å; Table 1 and Fig. 2) and by C—H···F hydrogen bonds between the naphthalene rings and the fluorine atoms on the benzene rings (C6—H6···F1ⁱⁱⁱ=2.44 Å; Table 1 and Fig. 3), resulting in the formation of molecular layers parallel to the ab plane. In addition, the layers interact through π–π interactions with centroid–centroid distances of 3.6115 (10) Å to form a three-dimensional structure.

The above mentioned results suggest that the title compound has similarities with 1,8-dibenzoyl-2,7-diethoxynaphthalene (Isogai et al., 2013) in the dihedral angles between the benzene rings and the naphthalene ring and the distance of the C—H···O hydrogen bond between the benzene ring and the ketonic carbonyl group.

Related literature top

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 top

To a 50 ml flask, 2,7-diethoxynaphthalene (2.0 mmol, 489 mg), 4-fluorobenzoic acid (5.6 mmol, 785 mg), and phosphorus pentoxide–methanesulfonic acid (8.8 ml) were placed. The reaction mixture was stirred at 60°C for 1.5 h. After the reaction, the mixture was poured into ice-cold water and extracted with 25 ml of CHCl₃ for three times. The combined extracts were washed with water, and 2 M aqueous NaOH followed by washing with brine. The organic layers thus obtained were dried over anhydrous MgSO₄. The solvent was removed under reduced pressure to give cake. The crude product was purified by reprecipitation (CHCl₃/methanol; isolated yield 91%). Furthermore, the isolated product was crystallized from CHCl₃ to give single-crystal suitable for X-ray analysis, m.p. 482.7–483.3 K.

Structure description top

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).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear (Rigaku/MSC, 2006); data reduction: CrystalClear (Rigaku/MSC, 2006); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of title molecule, with the atom numbering. The displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial view of the crystal packing of the title compound, showing the intermolecular C—H···O hydrogen bonds (see Table 1 for details; symmetry codes: (i) -1 + x, y, z; (ii) 1 + x, y, z).
	Fig. 3. A partial view of the crystal packing of the title compound, showing the intermolecular C—H···F hydrogen bonds (see Table 1 for details; symmetry codes: (iii) 1/2 - x, 1/2 + y, 1/2 - z).

[2,7-Diethoxy-8-(4-fluorobenzoyl)naphthalen-1-yl](4-fluorophenyl)methanone top

Crystal data top

C₂₈H₂₂F₂O₄	F(000) = 960
M_r = 460.46	D_x = 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

Data collection top

Rigaku Saturn70 diffractometer	3836 independent reflections
Radiation source: fine-focus sealed tube	3439 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 7.314 pixels mm^-1	θ_max = 25.0°, θ_min = 2.9°
ω scans	h = −9→9
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −25→24
T_min = 0.980, T_max = 0.980	l = −14→16
14368 measured reflections

Refinement top

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(F_o²) + (0.0756P)² + 0.3064P] where P = (F_o² + 2F_c²)/3
3836 reflections	(Δ/σ)_max < 0.001
309 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₈H₂₂F₂O₄	V = 2246.6 (9) Å³
M_r = 460.46	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.8592 (18) Å	µ = 0.10 mm⁻¹
b = 21.243 (5) Å	T = 173 K
c = 13.941 (3) Å	0.20 × 0.20 × 0.20 mm
β = 105.141 (3)°

Data collection top

Rigaku Saturn70 diffractometer	3836 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	3439 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.980	R_int = 0.031
14368 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.00	Δρ_max = 0.20 e Å⁻³
3836 reflections	Δρ_min = −0.18 e Å⁻³
309 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₂₈H₂₂F₂O₄
M_r	460.46
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	7.8592 (18), 21.243 (5), 13.941 (3)
β (°)	105.141 (3)
V (Å³)	2246.6 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku Saturn70
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.980, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	14368, 3836, 3439
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.108, 1.00
No. of reflections	3836
No. of parameters	309
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.18

Computer programs: CrystalClear (Rigaku/MSC, 2006), Il Milione (Burla et al., 2007), 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
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) x−1, y, z; (ii) x+1, y, z; (iii) −x+1/2, y+1/2, −z+1/2.

Acknowledgements

The authors express their gratitude to Associate Professor Hikaru Takaya and Professor Masaharu Nakamura, Institute for Chemical Research, Kyoto University, for their kind advice. This work was partially supported by the Collaborative Research Program of the Institute for Chemical Research, Kyoto University (grant No. 2012–72).

References

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609–613. 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
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan. Google Scholar
Isogai, A., Tsumuki, T., Murohashi, S., Okamoto, A. & Yonezawa, N. (2013). Acta Cryst. E69, o71. CSD CrossRef IUCr Journals Google Scholar
Nakaema, K., Watanabe, S., Okamoto, A., Noguchi, K. & Yonezawa, N. (2008). Acta Cryst. E64, o807. Web of Science CSD CrossRef IUCr Journals Google Scholar
Okamoto, A., Mitsui, R., Oike, H. & Yonezawa, N. (2011). Chem. Lett. 40, 1283–1284. Web of Science CrossRef CAS Google Scholar
Okamoto, A. & Yonezawa, N. (2009). Chem. Lett. 38, 914–915. Web of Science CrossRef CAS Google Scholar
Rigaku/MSC (2006). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Watanabe, S., Nagasawa, A., Okamoto, A., Noguchi, K. & Yonezawa, N. (2010). Acta Cryst. E66, o329. Web of Science CSD CrossRef IUCr Journals Google Scholar

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[2,7-Dieth­­oxy-8-(4-fluoro­benzo­yl)naphthalen-1-yl](4-fluoro­phen­yl)methanone

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[2,7-Diethoxy-8-(4-fluorobenzoyl)naphthalen-1-yl](4-fluorophenyl)methanone