(3,6-Dimeth­oxy-2-naphth­yl)(4-fluoro­benzo­yl)methanone

Watanabe, S.; Muto, T.; Nagasawa, A.; Okamoto, A.; Yonezawa, N.

doi:10.1107/S1600536810006859

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o712

doi:10.1107/S1600536810006859

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(3,6-Dimethoxy-2-naphthyl)(4-fluorobenzoyl)methanone

Shoji Watanabe,^a Toyokazu Muto,^a Atsushi Nagasawa,^a Akiko Okamoto ^a and Noriyuki Yonezawa ^a ^*

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

(Received 19 February 2010; accepted 23 February 2010; online 27 February 2010)

In the title compound, C₁₉H₁₅FO₃, the dihedral angle between the naphthalene ring system and the benzene ring is 62.93 (5)°. The bridging carbonyl C—C(=O)—C plane makes dihedral angles of 45.55 (6) and 28.62 (7)°, respectively, with the naphthalene ring system and the benzene ring. Weak intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions stabilize the crystal packing.

Related literature

For general background to the regioselective formation of peri-aroylnaphthalene compounds, see: Okamoto & Yonezawa (2009 ). For related structures, see: Hijikata et al. (2010 ); Mitsui et al. (2008 ); Nakaema et al. (2007 , 2008 ); Watanabe et al. (2010a ,b ).

Experimental

Crystal data

C₁₉H₁₅FO₃
M_r = 310.31
Monoclinic, P 2₁ /c
a = 8.3690 (2) Å
b = 19.7603 (5) Å
c = 9.3897 (2) Å
β = 105.126 (2)°
V = 1499.01 (6) Å³
Z = 4
Cu Kα radiation
μ = 0.84 mm⁻¹
T = 193 K
0.55 × 0.50 × 0.45 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ) T_min = 0.657, T_max = 0.705
26258 measured reflections
2738 independent reflections
2530 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.090
S = 1.02
2738 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.11 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C5/C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18B⋯Cg1ⁱ	0.98	2.85	3.7479 (14)	152
C17—H17⋯O1ⁱⁱ	0.95	2.55	3.2930 (16)	136
C18—H18A⋯O3ⁱⁱⁱ	0.98	2.39	3.3603 (16)	169
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x, -y, -z; (iii) x-1, y, z-1.

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 I, global. DOI: 10.1107/S1600536810006859/bt5198sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810006859/bt5198Isup2.hkl

checkCIF report

Comment top

In the course of our study on electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene, peri-aroylnaphthalene compounds have proven to be formed regioselectively with the aid of suitable acidic mediators (Okamoto & Yonezawa, 2009). The aroyl groups at the 1,8-positions of the naphthalene rings in these compounds are twisted almost perpendicularly but the benzene ring moieties of the aroyl groups tilt slightly toward the exo sides of the naphthalene rings.

Recently, we reported the structures of 1,8-diaroyl-2,7-dimethoxynaphthalenes, i. e., 1,8-bis(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Nakaema et al., 2007), bis(4-bromobenzoyl)(2,7-dimethoxynaphthalene-1,8-diyl)dimethanone (Watanabe et al., 2010a). In addition, the crystal structural analysis of 1-aroyl-2,7-dimethoxynaphthalenes, i. e., methyl 4-(2,7-dimethoxy-1-naphthoyl)benzoate (Hijikata et al., 2010) and 1-(4-nitorobenzoyl)-2,7-dimethoxynaphthalene (Watanabe et al. 2010b), also has revealed essentially the same non-coplanar structure as the 1,8-diaroylated naphthalenes.

Furthermore, the structure of 3-aroyl-2,7-dimetoxynaphthalenes such as 2-(4-chlorobenzoyl)-3,6-dimethoxynaphthalene (Nakaema et al., 2008), which are generally regarded to be thermodynamically more stable than the corresponding 1-positioned isomeric molecules, 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Mitsui et al., 2008), has been also studied. As a part of our ongoing work on the formation reaction and the structure of the aroylated naphthalene derivatives, the synthesis and crystal structure of (I), a 3-monoaroylnaphthalene bearing fluoro group, is discussed in this report. (I) was prepared by electrophilic aromatic aroylation reaction of 2,7-dimethoxynaphthalene with 4-fluorobenzoic acid.

An ORTEPIII (Burnett & Johnson, 1996) plot of (I) is displayed in Fig. 1. The 4-fluorophenyl group is twisted away from the attached naphthalene ring. The dihedral angle between the best planes of the fluorophenyl ring (C12—C17) and the naphthalene ring (C1—C10) is 62.93 (5)°. The bridging carbonyl plane (O1—C11—C3—C12) makes relatively large dihedral angle of 45.55 (6)° with the naphthalene ring (C1—C10) [C4—C3—C11—O1 torsion angle = 43.90 (17)°], whereas it makes rather small one of 28.62 (7)° with 4-fluorophenyl ring (C12—C17) [O1—C11—C12—C17 torsion angle = 28.69 (18)°].

Molecules are linked by C—H···π interactions (Fig. 2). The methyl group acts as an hydrogen-bond donor and π system of the naphthalene ring [C1—C5/C10 ring (with centroid Cg1)] of an adjacent molecule acts as an accepter (C18—H18B···π).

The crystal packing is additionally stabilized by two types of intermolecular weak C—H···O hydrogen bondings: One is between the aromatic hydrogen (H17) at meta position to the F group, and the carbonyl oxygen (O1) (Fig.3, Table 1). The other is between an hydrogen (H18A) of the 2-methoxy group which is situated adjacent to the fluorophenyl group, and the ethereal oxygen (O3) of the 7-methoxy group in a neighboring molecule .

Related literature top

For general background to the regioselective formation of peri-aroylnaphthalene compounds, see: Okamoto & Yonezawa (2009). For related structures, see: Hijikata et al. (2010); Mitsui et al. (2008); Nakaema et al. (2007, 2008); Watanabe et al. (2010a,b).

Experimental top

The title compound was prepared by treatment of a mixture of 2,7-dimethoxynaphthalene (0.20 mmol) and 4-fluoroobenzoic acid (0.21 mmol) with phosphorus pentoxide–methanesulfonic acid mixture (P₂O₅–MsOH [1/10 w/w]; 0.44 ml) at 60°C for 24 hours followed by a typical work-up procedure (30% yield; Okamoto & Yonezawa, 2009). Colorless block single crystals suitable for X-ray diffraction were obtained by recrystallization from chloroform.

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.
	Fig. 2. C—H···π interactions (green dotted lines).
	Fig. 3. Two types of intermolecular weak C—H···O interactions (blue dotted lines).

(3,6-Dimethoxy-2-naphthyl)(4-fluorobenzoyl)methanone top

Crystal data top

C₁₉H₁₅FO₃	F(000) = 648
M_r = 310.31	D_x = 1.375 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 409.7–410.3 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54187 Å
a = 8.3690 (2) Å	Cell parameters from 20173 reflections
b = 19.7603 (5) Å	θ = 4.5–68.2°
c = 9.3897 (2) Å	µ = 0.84 mm⁻¹
β = 105.126 (2)°	T = 193 K
V = 1499.01 (6) Å³	Block, colorless
Z = 4	0.55 × 0.50 × 0.45 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2738 independent reflections
Radiation source: fine-focus sealed tube	2530 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 10.00 pixels mm^-1	θ_max = 68.2°, θ_min = 4.5°
ω scans	h = −10→9
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −23→23
T_min = 0.657, T_max = 0.705	l = −11→11
26258 measured reflections

Refinement top

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)] = 0.032	H-atom parameters constrained
wR(F²) = 0.090	w = 1/[σ²(F_o²) + (0.0489P)² + 0.3826P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2738 reflections	Δρ_max = 0.20 e Å⁻³
211 parameters	Δρ_min = −0.11 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: 0.0068 (5)

Crystal data top

C₁₉H₁₅FO₃	V = 1499.01 (6) Å³
M_r = 310.31	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 8.3690 (2) Å	µ = 0.84 mm⁻¹
b = 19.7603 (5) Å	T = 193 K
c = 9.3897 (2) Å	0.55 × 0.50 × 0.45 mm
β = 105.126 (2)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2738 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	2530 reflections with I > 2σ(I)
T_min = 0.657, T_max = 0.705	R_int = 0.023
26258 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.02	Δρ_max = 0.20 e Å⁻³
2738 reflections	Δρ_min = −0.11 e Å⁻³
211 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.23655 (12)	0.05261 (4)	−0.47975 (8)	0.0590 (3)
O1	0.24071 (11)	0.01533 (5)	0.18556 (10)	0.0455 (2)
O2	0.27326 (11)	0.19750 (4)	0.05828 (9)	0.0398 (2)
O3	0.94318 (11)	0.28084 (5)	0.70653 (10)	0.0440 (2)
C1	0.49935 (15)	0.22971 (6)	0.26543 (13)	0.0323 (3)
H1	0.4904	0.2759	0.2362	0.039*
C2	0.39672 (14)	0.18266 (6)	0.18062 (12)	0.0320 (3)
C3	0.41037 (14)	0.11285 (6)	0.22130 (12)	0.0324 (3)
C4	0.52148 (14)	0.09433 (6)	0.35119 (13)	0.0336 (3)
H4	0.5262	0.0483	0.3813	0.040*
C5	0.62836 (14)	0.14138 (6)	0.44084 (12)	0.0318 (3)
C6	0.74594 (15)	0.12300 (6)	0.57403 (13)	0.0365 (3)
H6	0.7542	0.0771	0.6052	0.044*
C7	0.84681 (15)	0.17022 (6)	0.65743 (13)	0.0384 (3)
H7	0.9247	0.1571	0.7461	0.046*
C8	0.83613 (14)	0.23878 (6)	0.61265 (13)	0.0349 (3)
C9	0.72528 (14)	0.25877 (6)	0.48456 (13)	0.0329 (3)
H9	0.7199	0.3049	0.4551	0.039*
C10	0.61869 (14)	0.21041 (6)	0.39610 (12)	0.0306 (3)
C11	0.30651 (14)	0.05923 (6)	0.12869 (13)	0.0342 (3)
C12	0.29002 (14)	0.05826 (6)	−0.03341 (13)	0.0325 (3)
C13	0.41406 (15)	0.08347 (6)	−0.09276 (14)	0.0377 (3)
H13	0.5108	0.1027	−0.0294	0.045*
C14	0.39778 (17)	0.08070 (6)	−0.24310 (15)	0.0428 (3)
H14	0.4831	0.0969	−0.2839	0.051*
C15	0.25461 (17)	0.05384 (6)	−0.33183 (13)	0.0409 (3)
C16	0.13017 (16)	0.02778 (7)	−0.27807 (14)	0.0420 (3)
H16	0.0334	0.0090	−0.3424	0.050*
C17	0.14990 (15)	0.02967 (6)	−0.12746 (14)	0.0382 (3)
H17	0.0663	0.0111	−0.0874	0.046*
C18	0.23490 (16)	0.26755 (6)	0.02792 (14)	0.0402 (3)
H18A	0.1387	0.2715	−0.0575	0.048*
H18B	0.3300	0.2904	0.0065	0.048*
H18C	0.2098	0.2887	0.1140	0.048*
C19	0.92919 (19)	0.35155 (7)	0.67676 (16)	0.0505 (4)
H19A	1.0101	0.3760	0.7539	0.061*
H19B	0.8173	0.3668	0.6752	0.061*
H19C	0.9506	0.3606	0.5808	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0822 (6)	0.0620 (5)	0.0351 (4)	−0.0059 (4)	0.0196 (4)	−0.0056 (4)
O1	0.0478 (5)	0.0476 (5)	0.0395 (5)	−0.0152 (4)	0.0088 (4)	0.0038 (4)
O2	0.0411 (5)	0.0351 (5)	0.0353 (4)	0.0021 (4)	−0.0042 (4)	−0.0002 (3)
O3	0.0421 (5)	0.0433 (5)	0.0387 (5)	−0.0027 (4)	−0.0039 (4)	−0.0046 (4)
C1	0.0351 (6)	0.0297 (6)	0.0313 (6)	0.0017 (5)	0.0071 (5)	0.0016 (4)
C2	0.0311 (6)	0.0352 (6)	0.0284 (5)	0.0017 (5)	0.0056 (4)	0.0004 (5)
C3	0.0319 (6)	0.0340 (6)	0.0315 (6)	−0.0009 (5)	0.0085 (5)	−0.0006 (5)
C4	0.0359 (6)	0.0310 (6)	0.0346 (6)	0.0009 (5)	0.0104 (5)	0.0021 (5)
C5	0.0314 (6)	0.0334 (6)	0.0310 (6)	0.0023 (4)	0.0090 (5)	0.0009 (4)
C6	0.0382 (6)	0.0353 (6)	0.0348 (6)	0.0044 (5)	0.0073 (5)	0.0043 (5)
C7	0.0368 (6)	0.0433 (7)	0.0311 (6)	0.0059 (5)	0.0015 (5)	0.0031 (5)
C8	0.0314 (6)	0.0400 (7)	0.0319 (6)	0.0005 (5)	0.0058 (5)	−0.0045 (5)
C9	0.0335 (6)	0.0321 (6)	0.0325 (6)	0.0012 (5)	0.0078 (5)	−0.0004 (5)
C10	0.0298 (6)	0.0333 (6)	0.0295 (6)	0.0017 (4)	0.0092 (4)	−0.0001 (4)
C11	0.0316 (6)	0.0320 (6)	0.0383 (6)	−0.0011 (5)	0.0081 (5)	0.0018 (5)
C12	0.0336 (6)	0.0273 (5)	0.0364 (6)	−0.0008 (4)	0.0085 (5)	−0.0014 (4)
C13	0.0374 (6)	0.0334 (6)	0.0427 (7)	−0.0064 (5)	0.0111 (5)	−0.0051 (5)
C14	0.0520 (8)	0.0349 (6)	0.0479 (7)	−0.0058 (5)	0.0247 (6)	−0.0038 (5)
C15	0.0562 (8)	0.0339 (6)	0.0336 (6)	0.0034 (5)	0.0136 (6)	−0.0033 (5)
C16	0.0415 (7)	0.0423 (7)	0.0389 (7)	−0.0020 (5)	0.0048 (5)	−0.0063 (5)
C17	0.0356 (6)	0.0387 (6)	0.0403 (6)	−0.0061 (5)	0.0103 (5)	−0.0026 (5)
C18	0.0400 (7)	0.0370 (6)	0.0376 (7)	0.0032 (5)	−0.0007 (5)	0.0047 (5)
C19	0.0513 (8)	0.0409 (7)	0.0509 (8)	−0.0057 (6)	−0.0018 (6)	−0.0071 (6)

Geometric parameters (Å, º) top

F1—C15	1.3575 (14)	C8—C9	1.3715 (16)
O1—C11	1.2224 (15)	C9—C10	1.4186 (16)
O2—C2	1.3615 (14)	C9—H9	0.9500
O2—C18	1.4327 (15)	C11—C12	1.4922 (16)
O3—C8	1.3632 (14)	C12—C17	1.3906 (17)
O3—C19	1.4238 (16)	C12—C13	1.3922 (17)
C1—C2	1.3709 (16)	C13—C14	1.3835 (18)
C1—C10	1.4174 (16)	C13—H13	0.9500
C1—H1	0.9500	C14—C15	1.3750 (19)
C2—C3	1.4279 (16)	C14—H14	0.9500
C3—C4	1.3763 (16)	C15—C16	1.3708 (19)
C3—C11	1.4965 (16)	C16—C17	1.3808 (18)
C4—C5	1.4072 (16)	C16—H16	0.9500
C4—H4	0.9500	C17—H17	0.9500
C5—C6	1.4219 (16)	C18—H18A	0.9800
C5—C10	1.4232 (16)	C18—H18B	0.9800
C6—C7	1.3608 (18)	C18—H18C	0.9800
C6—H6	0.9500	C19—H19A	0.9800
C7—C8	1.4144 (17)	C19—H19B	0.9800
C7—H7	0.9500	C19—H19C	0.9800

C2—O2—C18	117.22 (9)	O1—C11—C3	120.54 (11)
C8—O3—C19	117.70 (10)	C12—C11—C3	119.14 (10)
C2—C1—C10	120.89 (11)	C17—C12—C13	118.98 (11)
C2—C1—H1	119.6	C17—C12—C11	119.42 (10)
C10—C1—H1	119.6	C13—C12—C11	121.57 (11)
O2—C2—C1	124.50 (11)	C14—C13—C12	120.60 (12)
O2—C2—C3	115.09 (10)	C14—C13—H13	119.7
C1—C2—C3	120.37 (10)	C12—C13—H13	119.7
C4—C3—C2	118.84 (11)	C15—C14—C13	118.15 (12)
C4—C3—C11	118.84 (11)	C15—C14—H14	120.9
C2—C3—C11	122.32 (10)	C13—C14—H14	120.9
C3—C4—C5	122.10 (11)	F1—C15—C16	118.53 (12)
C3—C4—H4	118.9	F1—C15—C14	118.26 (12)
C5—C4—H4	118.9	C16—C15—C14	123.20 (12)
C4—C5—C6	122.91 (11)	C15—C16—C17	117.88 (12)
C4—C5—C10	118.57 (10)	C15—C16—H16	121.1
C6—C5—C10	118.52 (11)	C17—C16—H16	121.1
C7—C6—C5	120.93 (11)	C16—C17—C12	121.13 (11)
C7—C6—H6	119.5	C16—C17—H17	119.4
C5—C6—H6	119.5	C12—C17—H17	119.4
C6—C7—C8	120.28 (11)	O2—C18—H18A	109.5
C6—C7—H7	119.9	O2—C18—H18B	109.5
C8—C7—H7	119.9	H18A—C18—H18B	109.5
O3—C8—C9	124.86 (11)	O2—C18—H18C	109.5
O3—C8—C7	114.32 (10)	H18A—C18—H18C	109.5
C9—C8—C7	120.82 (11)	H18B—C18—H18C	109.5
C8—C9—C10	119.84 (11)	O3—C19—H19A	109.5
C8—C9—H9	120.1	O3—C19—H19B	109.5
C10—C9—H9	120.1	H19A—C19—H19B	109.5
C1—C10—C9	121.26 (11)	O3—C19—H19C	109.5
C1—C10—C5	119.10 (10)	H19A—C19—H19C	109.5
C9—C10—C5	119.61 (10)	H19B—C19—H19C	109.5
O1—C11—C12	120.27 (11)

C18—O2—C2—C1	−8.47 (17)	C8—C9—C10—C5	−0.31 (17)
C18—O2—C2—C3	169.07 (10)	C4—C5—C10—C1	1.65 (16)
C10—C1—C2—O2	176.29 (10)	C6—C5—C10—C1	−178.51 (11)
C10—C1—C2—C3	−1.12 (18)	C4—C5—C10—C9	−179.93 (10)
O2—C2—C3—C4	−173.95 (10)	C6—C5—C10—C9	−0.08 (16)
C1—C2—C3—C4	3.70 (17)	C4—C3—C11—O1	43.90 (16)
O2—C2—C3—C11	5.21 (16)	C2—C3—C11—O1	−135.26 (12)
C1—C2—C3—C11	−177.14 (11)	C4—C3—C11—C12	−133.52 (12)
C2—C3—C4—C5	−3.63 (17)	C2—C3—C11—C12	47.32 (16)
C11—C3—C4—C5	177.18 (10)	O1—C11—C12—C17	28.70 (17)
C3—C4—C5—C6	−178.86 (11)	C3—C11—C12—C17	−153.88 (11)
C3—C4—C5—C10	0.98 (17)	O1—C11—C12—C13	−149.31 (12)
C4—C5—C6—C7	−179.94 (11)	C3—C11—C12—C13	28.11 (16)
C10—C5—C6—C7	0.22 (18)	C17—C12—C13—C14	0.55 (18)
C5—C6—C7—C8	0.02 (19)	C11—C12—C13—C14	178.57 (11)
C19—O3—C8—C9	5.92 (18)	C12—C13—C14—C15	1.42 (19)
C19—O3—C8—C7	−174.07 (11)	C13—C14—C15—F1	178.38 (11)
C6—C7—C8—O3	179.56 (11)	C13—C14—C15—C16	−2.2 (2)
C6—C7—C8—C9	−0.42 (18)	F1—C15—C16—C17	−179.69 (11)
O3—C8—C9—C10	−179.42 (10)	C14—C15—C16—C17	0.9 (2)
C7—C8—C9—C10	0.56 (17)	C15—C16—C17—C12	1.21 (19)
C2—C1—C10—C9	−179.95 (10)	C13—C12—C17—C16	−1.91 (18)
C2—C1—C10—C5	−1.55 (17)	C11—C12—C17—C16	−179.97 (11)
C8—C9—C10—C1	178.08 (11)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C5/C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···Cg1ⁱ	0.98	2.85	3.7479 (14)	152
C17—H17···O1ⁱⁱ	0.95	2.55	3.2930 (16)	136
C18—H18A···O3ⁱⁱⁱ	0.98	2.39	3.3603 (16)	169

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅FO₃
M_r	310.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	193
a, b, c (Å)	8.3690 (2), 19.7603 (5), 9.3897 (2)
β (°)	105.126 (2)
V (Å³)	1499.01 (6)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.84
Crystal size (mm)	0.55 × 0.50 × 0.45

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.657, 0.705
No. of measured, independent and observed [I > 2σ(I)] reflections	26258, 2738, 2530
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.090, 1.02
No. of reflections	2738
No. of parameters	211
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.11

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

Cg1 is the centroid of the C1–C5/C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···Cg1ⁱ	0.98	2.85	3.7479 (14)	152
C17—H17···O1ⁱⁱ	0.95	2.55	3.2930 (16)	136
C18—H18A···O3ⁱⁱⁱ	0.98	2.39	3.3603 (16)	169

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

Acknowledgements

The authors would express their gratitude to professor Keiichi Noguchi for his technical advice. This work was partially supported by the Ogasawara Foundation for the Promotion of Science & Engineering, Tokyo, Japan.

References

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Volume 66| Part 3| March 2010| Page o712

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