(2,7-Dimeth­oxy­naphthalen-1-yl)(4-fluoro­phen­yl)methanone

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

doi:10.1107/S1600536811018332

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1466

doi:10.1107/S1600536811018332

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(2,7-Dimethoxynaphthalen-1-yl)(4-fluorophenyl)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: aokamoto@cc.tuat.ac.jp

(Received 7 May 2011; accepted 14 May 2011; online 20 May 2011)

In the title compound, C₁₉H₁₅FO₃, the dihedral angle between the naphthalene ring system and the benzene ring is 80.46 (4)°. In the crystal, molecules are linked by intermolecular C—H⋯O hydrogen bonds into chains parallel to the b axis.

Related literature

For the formation reaction of aroylated naphthalene compounds via electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene, see: Okamoto & Yonezawa (2009 ). For related structures reported by our group, see: Kato et al. (2010 ); Muto et al. (2010 ); Watanabe, Nagasawa et al. (2010 ); Watanabe, Nakaema, Muto et al. (2010 ); Watanabe, Nakaema, Nishijima et al. (2010 ).

Experimental

Crystal data

C₁₉H₁₅FO₃
M_r = 310.31
Monoclinic, P 2₁ /n
a = 10.9714 (2) Å
b = 7.51791 (14) Å
c = 18.7832 (3) Å
β = 99.917 (1)°
V = 1526.13 (5) Å³
Z = 4
Cu Kα radiation
μ = 0.82 mm⁻¹
T = 193 K
0.40 × 0.30 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ) T_min = 0.735, T_max = 0.853
26625 measured reflections
2789 independent reflections
2566 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.109
S = 1.01
2789 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O1ⁱ	0.95	2.35	3.2139 (15)	151
Symmetry code: (i) x, y+1, z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018332/rz2596sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811018332/rz2596Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811018332/rz2596Isup3.cml

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., (2,7-dimethoxynaphthalene-1,8-diyl)bis(4-fluorophenyl)dimethanone (Watanabe, Nagasawa et al., 2010), bis(4-bromophenyl)(2,7-dimethoxynaphthalene-1,8-diyl)dimethanone (Watanabe, Nakaema, Muto et al., 2010), and [2,7-dimethoxy-8-(4-methylbenzoyl)-1-naphthyl](4-methylphenyl)methanone (Muto et al., 2010). Furthermore, the crystal structures of 1-aroyl-2,7-dimethoxynaphthalenes, i. e., 2,7-dimethoxy-1-(4-nitrobenzoyl)naphthalene (Watanabe, Nakaema, Nishijima et al., 2010) and (2,7-dimethoxynaphthalen-1-yl)(phenyl)methanone (Kato et al., 2010), also exhibit essentially the same non-coplanar structure as the 1,8-diaroylated naphthalenes. As a part of our ongoing studies on the formation and the structure of the aroylated naphthalene derivatives, the synthesis and crystal structure of (I), a 1-monoaroylnaphthalene bearing fluoro group, is discussed in this report. (I) was prepared by electrophilic aromatic aroylation reaction of 2,7-dimethoxynaphthalene with 4-fluorobenzoyl chloride.

The molecular structure of (I) is displayed in Fig. 1. The interplanar angle between the benzene ring (C12—C17) and the naphthalene ring (C1—C10) is 80.46 (4)°. The torsion angle between the carbonyl group and the naphthalene ring [C10–C1–C11–O1 = -77.77 (13)°] is larger than that between the carbonyl group and fluorophenyl ring [O1–C11–C12–C17 = 4.20 (15)°].

In the crystal packing, the molecules are aligned consecutively in stacks along the b axis (Fig. 2). This stack of naphthalene rings occludes the adjacent counter part and vice versa. The crystal packing is stabilized by weak intermolecular C—H···O hydrogen bond between the hydrogen atom of the 4-fluorophenyl group and the carbonyl oxygen atom (Table 1; Fig. 3).

Related literature top

For the formation reaction of aroylated naphthalene compounds via electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene, see: Okamoto & Yonezawa (2009). For related structures reported by our group, see: Kato et al. (2010); Muto et al. (2010); Watanabe, Nagasawa et al. (2010); Watanabe, Nakaema, Muto et al. (2010); Watanabe, Nakaema, Nishijima et al. (2010).

Experimental top

The title compound was prepared by treatment of a mixture of 2,7-dimethoxynaphthalene (75.29 mg, 0.4 mmol), 4-fluorobenzoyl chloride (69.77 mg, 0.44 mmol), CH₂Cl₂ (1 ml) with AlCl₃ (0.48 mmol, 64.00 mg). After the reaction mixture was stirred at 273 K for 3 h, the mixture was poured into ice-cooled water and extracted with CHCl₃ (10 ml × 3). The combined extracts were washed with 2 M aqueous NaOH followed by washing with brine. The organic layer thus obtained was dried over anhydrous MgSO₄. The solvent was removed under reduced pressure to give cake. The crude product was purified by recrystallization from ethanol (isolated yield 76%). Colourless platelet single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution (m.p. 381 K). Anal. Calcd for C₁₉H₁₅O₃F: C, 73.54; H, 4.87. Found: C, 73.45; H, 4.83. Spectroscopic data:

¹H NMR (300 MHz, CDCl₃. p.p.m.) 3.67 (3H, s), 3.75 (3H, s), 6.79 (1H, d, J = 2.4 Hz), 6.70 (1H, dd, J = 9.0, 2.4 Hz), 7.07 (2H, dd, J = 9.0, 9.0 Hz), 7.12 (1H, d, J = 9.0 Hz), 7.69 (1H, d, J = 9.0 Hz), 7.83 (1H, d, J = 9.0 Hz), 7.87 (2H, dd, J = 5.7, 8.7 Hz);

¹³C NMR (75.0 MHz, CDCl₃, p.p.m.); 55.2945, 56.4131, 102.1511, 110.2777, 115.7894 (J_C–F = 22.39 Hz), 117.2283, 121.4923, 124.5039, 129.8388, 131.2824, 132.3007 (J_C–F = 9.39 Hz), 133.0798, 134.6669 (J_C–F = 2.88 Hz), 155.0597, 159.0656, 166.0784 (J_C–F = 255.03 Hz), 196.5529;

IR (KBr, cm^-1): 1662, 1627, 1597, 1513, 1279, 1242;

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: ORTEP (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids.
	Fig. 2. The alignment of the molecules in the crystal structure, viewed down the b axis.
	Fig. 3. C–H···O interaction between hydrogen atom of fluorophenyl ring and carbonyl oxygen atom.

(2,7-Dimethoxynaphthalen-1-yl)(4-fluorophenyl)methanone top

Crystal data top

C₁₉H₁₅FO₃	F(000) = 648
M_r = 310.31	D_x = 1.351 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 381 K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54187 Å
a = 10.9714 (2) Å	Cell parameters from 24946 reflections
b = 7.51791 (14) Å	θ = 4.1–68.3°
c = 18.7832 (3) Å	µ = 0.82 mm⁻¹
β = 99.917 (1)°	T = 193 K
V = 1526.13 (5) Å³	Platelet, colourless
Z = 4	0.40 × 0.30 × 0.20 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2789 independent reflections
Radiation source: fine-focus sealed tube	2566 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 10.00 pixels mm^-1	θ_max = 68.3°, θ_min = 4.4°
ω scans	h = −13→13
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −9→9
T_min = 0.735, T_max = 0.853	l = −22→22
26625 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)] = 0.034	H-atom parameters constrained
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0726P)² + 0.253P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
2789 reflections	Δρ_max = 0.23 e Å⁻³
211 parameters	Δρ_min = −0.15 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: 0.0116 (8)

Crystal data top

C₁₉H₁₅FO₃	V = 1526.13 (5) Å³
M_r = 310.31	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 10.9714 (2) Å	µ = 0.82 mm⁻¹
b = 7.51791 (14) Å	T = 193 K
c = 18.7832 (3) Å	0.40 × 0.30 × 0.20 mm
β = 99.917 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2789 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	2566 reflections with I > 2σ(I)
T_min = 0.735, T_max = 0.853	R_int = 0.036
26625 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.01	Δρ_max = 0.23 e Å⁻³
2789 reflections	Δρ_min = −0.15 e Å⁻³
211 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	0.88989 (8)	1.11551 (11)	0.39053 (4)	0.0625 (3)
O1	0.83508 (8)	0.41722 (11)	0.56528 (4)	0.0452 (2)
O2	0.56864 (7)	0.61906 (13)	0.58208 (4)	0.0467 (3)
O3	1.18714 (7)	0.58367 (13)	0.78977 (5)	0.0485 (3)
C1	0.76748 (10)	0.61523 (14)	0.64820 (6)	0.0316 (3)
C2	0.64274 (10)	0.63620 (15)	0.64810 (6)	0.0366 (3)
C3	0.59851 (10)	0.67163 (16)	0.71271 (6)	0.0407 (3)
H3	0.5124	0.6863	0.7123	0.049*
C4	0.68059 (11)	0.68475 (15)	0.77614 (6)	0.0391 (3)
H4	0.6504	0.7093	0.8196	0.047*
C5	0.80873 (10)	0.66282 (14)	0.77862 (6)	0.0345 (3)
C6	0.89515 (11)	0.67527 (16)	0.84395 (6)	0.0403 (3)
H6	0.8663	0.7023	0.8876	0.048*
C7	1.01804 (11)	0.64943 (17)	0.84565 (6)	0.0426 (3)
H7	1.0742	0.6570	0.8901	0.051*
C8	1.06219 (10)	0.61110 (15)	0.78062 (6)	0.0374 (3)
C9	0.98303 (10)	0.60226 (14)	0.71590 (6)	0.0332 (3)
H9	1.0143	0.5797	0.6726	0.040*
C10	0.85384 (10)	0.62683 (13)	0.71348 (5)	0.0312 (3)
C11	0.81034 (9)	0.57083 (14)	0.57830 (5)	0.0317 (3)
C12	0.82601 (9)	0.71631 (14)	0.52758 (5)	0.0315 (3)
C13	0.79565 (10)	0.89121 (15)	0.54125 (6)	0.0391 (3)
H13	0.7610	0.9179	0.5830	0.047*
C14	0.81544 (11)	1.02663 (16)	0.49468 (7)	0.0450 (3)
H14	0.7940	1.1461	0.5034	0.054*
C15	0.86713 (11)	0.98285 (17)	0.43532 (6)	0.0435 (3)
C16	0.89914 (10)	0.81228 (17)	0.42000 (6)	0.0425 (3)
H16	0.9352	0.7874	0.3786	0.051*
C17	0.87757 (10)	0.67828 (16)	0.46618 (6)	0.0367 (3)
H17	0.8979	0.5590	0.4563	0.044*
C18	0.43866 (11)	0.6376 (2)	0.57767 (8)	0.0608 (4)
H18A	0.3977	0.6210	0.5275	0.073*
H18B	0.4200	0.7567	0.5941	0.073*
H18C	0.4087	0.5480	0.6084	0.073*
C19	1.23927 (11)	0.5406 (2)	0.72769 (7)	0.0501 (3)
H19A	1.3281	0.5187	0.7421	0.060*
H19B	1.2264	0.6399	0.6934	0.060*
H19C	1.1992	0.4336	0.7048	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0694 (5)	0.0562 (5)	0.0572 (5)	−0.0178 (4)	−0.0021 (4)	0.0216 (4)
O1	0.0652 (6)	0.0331 (5)	0.0399 (5)	0.0095 (4)	0.0167 (4)	−0.0010 (3)
O2	0.0323 (4)	0.0658 (6)	0.0400 (5)	0.0059 (4)	0.0003 (3)	−0.0088 (4)
O3	0.0354 (4)	0.0644 (6)	0.0426 (5)	−0.0001 (4)	−0.0025 (3)	−0.0037 (4)
C1	0.0346 (5)	0.0299 (5)	0.0307 (5)	0.0018 (4)	0.0066 (4)	−0.0017 (4)
C2	0.0355 (6)	0.0369 (6)	0.0367 (6)	0.0024 (4)	0.0038 (4)	−0.0040 (4)
C3	0.0346 (6)	0.0434 (6)	0.0464 (6)	0.0019 (5)	0.0133 (5)	−0.0059 (5)
C4	0.0453 (6)	0.0375 (6)	0.0375 (6)	0.0000 (5)	0.0154 (5)	−0.0052 (5)
C5	0.0423 (6)	0.0294 (5)	0.0326 (5)	−0.0016 (4)	0.0091 (4)	−0.0014 (4)
C6	0.0523 (7)	0.0396 (6)	0.0299 (5)	−0.0029 (5)	0.0092 (5)	−0.0032 (4)
C7	0.0487 (7)	0.0451 (7)	0.0307 (6)	−0.0029 (5)	−0.0027 (5)	−0.0017 (5)
C8	0.0362 (6)	0.0367 (6)	0.0379 (6)	−0.0031 (4)	0.0019 (4)	0.0004 (4)
C9	0.0355 (6)	0.0330 (6)	0.0313 (5)	−0.0018 (4)	0.0062 (4)	−0.0003 (4)
C10	0.0363 (6)	0.0262 (5)	0.0313 (5)	−0.0012 (4)	0.0064 (4)	−0.0004 (4)
C11	0.0297 (5)	0.0342 (6)	0.0299 (5)	0.0030 (4)	0.0013 (4)	−0.0033 (4)
C12	0.0281 (5)	0.0345 (6)	0.0300 (5)	0.0016 (4)	−0.0002 (4)	−0.0020 (4)
C13	0.0412 (6)	0.0367 (6)	0.0381 (6)	0.0033 (4)	0.0032 (5)	−0.0040 (5)
C14	0.0483 (7)	0.0324 (6)	0.0500 (7)	−0.0001 (5)	−0.0038 (5)	0.0006 (5)
C15	0.0399 (6)	0.0454 (7)	0.0407 (6)	−0.0092 (5)	−0.0061 (5)	0.0116 (5)
C16	0.0400 (6)	0.0542 (7)	0.0327 (6)	−0.0020 (5)	0.0044 (4)	0.0036 (5)
C17	0.0359 (5)	0.0410 (6)	0.0323 (5)	0.0044 (4)	0.0036 (4)	−0.0012 (4)
C18	0.0351 (7)	0.0828 (11)	0.0602 (8)	0.0114 (6)	−0.0034 (6)	−0.0184 (8)
C19	0.0356 (6)	0.0621 (8)	0.0513 (7)	0.0045 (5)	0.0038 (5)	−0.0006 (6)

Geometric parameters (Å, º) top

F1—C15	1.3554 (13)	C8—C9	1.3685 (15)
O1—C11	1.2207 (13)	C9—C10	1.4223 (15)
O2—C2	1.3668 (13)	C9—H9	0.9500
O2—C18	1.4210 (14)	C11—C12	1.4798 (15)
O3—C8	1.3676 (13)	C12—C13	1.3912 (15)
O3—C19	1.4217 (15)	C12—C17	1.3988 (15)
C1—C2	1.3773 (15)	C13—C14	1.3835 (17)
C1—C10	1.4173 (15)	C13—H13	0.9500
C1—C11	1.5063 (14)	C14—C15	1.3752 (18)
C2—C3	1.4078 (16)	C14—H14	0.9500
C3—C4	1.3676 (17)	C15—C16	1.3731 (18)
C3—H3	0.9500	C16—C17	1.3762 (17)
C4—C5	1.4083 (16)	C16—H16	0.9500
C4—H4	0.9500	C17—H17	0.9500
C5—C6	1.4188 (16)	C18—H18A	0.9800
C5—C10	1.4227 (15)	C18—H18B	0.9800
C6—C7	1.3572 (17)	C18—H18C	0.9800
C6—H6	0.9500	C19—H19A	0.9800
C7—C8	1.4189 (16)	C19—H19B	0.9800
C7—H7	0.9500	C19—H19C	0.9800

C2—O2—C18	118.54 (10)	O1—C11—C1	119.86 (9)
C8—O3—C19	117.86 (9)	C12—C11—C1	119.06 (9)
C2—C1—C10	120.68 (10)	C13—C12—C17	119.28 (10)
C2—C1—C11	118.92 (9)	C13—C12—C11	121.45 (10)
C10—C1—C11	120.34 (9)	C17—C12—C11	119.21 (10)
O2—C2—C1	115.21 (9)	C14—C13—C12	120.68 (11)
O2—C2—C3	124.09 (10)	C14—C13—H13	119.7
C1—C2—C3	120.70 (10)	C12—C13—H13	119.7
C4—C3—C2	119.44 (10)	C15—C14—C13	117.91 (11)
C4—C3—H3	120.3	C15—C14—H14	121.0
C2—C3—H3	120.3	C13—C14—H14	121.0
C3—C4—C5	121.61 (10)	F1—C15—C16	118.42 (11)
C3—C4—H4	119.2	F1—C15—C14	118.23 (12)
C5—C4—H4	119.2	C16—C15—C14	123.33 (11)
C4—C5—C6	122.38 (10)	C15—C16—C17	118.27 (11)
C4—C5—C10	119.14 (10)	C15—C16—H16	120.9
C6—C5—C10	118.48 (10)	C17—C16—H16	120.9
C7—C6—C5	121.60 (10)	C16—C17—C12	120.52 (11)
C7—C6—H6	119.2	C16—C17—H17	119.7
C5—C6—H6	119.2	C12—C17—H17	119.7
C6—C7—C8	119.60 (10)	O2—C18—H18A	109.5
C6—C7—H7	120.2	O2—C18—H18B	109.5
C8—C7—H7	120.2	H18A—C18—H18B	109.5
O3—C8—C9	124.99 (10)	O2—C18—H18C	109.5
O3—C8—C7	113.94 (10)	H18A—C18—H18C	109.5
C9—C8—C7	121.07 (10)	H18B—C18—H18C	109.5
C8—C9—C10	119.91 (10)	O3—C19—H19A	109.5
C8—C9—H9	120.0	O3—C19—H19B	109.5
C10—C9—H9	120.0	H19A—C19—H19B	109.5
C1—C10—C5	118.42 (10)	O3—C19—H19C	109.5
C1—C10—C9	122.26 (9)	H19A—C19—H19C	109.5
C5—C10—C9	119.31 (10)	H19B—C19—H19C	109.5
O1—C11—C12	121.05 (9)

C18—O2—C2—C1	179.54 (11)	C4—C5—C10—C1	0.29 (15)
C18—O2—C2—C3	−0.10 (18)	C6—C5—C10—C1	−179.72 (10)
C10—C1—C2—O2	−178.91 (9)	C4—C5—C10—C9	−179.17 (10)
C11—C1—C2—O2	−1.87 (15)	C6—C5—C10—C9	0.82 (15)
C10—C1—C2—C3	0.74 (17)	C8—C9—C10—C1	−178.60 (10)
C11—C1—C2—C3	177.78 (10)	C8—C9—C10—C5	0.85 (15)
O2—C2—C3—C4	179.43 (11)	C2—C1—C11—O1	−99.28 (12)
C1—C2—C3—C4	−0.19 (18)	C10—C1—C11—O1	77.78 (13)
C2—C3—C4—C5	−0.31 (18)	C2—C1—C11—C12	82.89 (13)
C3—C4—C5—C6	−179.74 (11)	C10—C1—C11—C12	−100.06 (11)
C3—C4—C5—C10	0.25 (17)	O1—C11—C12—C13	178.65 (10)
C4—C5—C6—C7	178.35 (11)	C1—C11—C12—C13	−3.54 (14)
C10—C5—C6—C7	−1.64 (17)	O1—C11—C12—C17	−4.20 (15)
C5—C6—C7—C8	0.78 (18)	C1—C11—C12—C17	173.60 (9)
C19—O3—C8—C9	−0.77 (18)	C17—C12—C13—C14	0.30 (16)
C19—O3—C8—C7	178.67 (11)	C11—C12—C13—C14	177.44 (10)
C6—C7—C8—O3	−178.50 (11)	C12—C13—C14—C15	−0.74 (17)
C6—C7—C8—C9	0.96 (18)	C13—C14—C15—F1	−178.23 (10)
O3—C8—C9—C10	177.64 (10)	C13—C14—C15—C16	0.37 (17)
C7—C8—C9—C10	−1.76 (17)	F1—C15—C16—C17	179.06 (10)
C2—C1—C10—C5	−0.78 (16)	C14—C15—C16—C17	0.45 (17)
C11—C1—C10—C5	−177.78 (9)	C15—C16—C17—C12	−0.91 (16)
C2—C1—C10—C9	178.67 (10)	C13—C12—C17—C16	0.55 (15)
C11—C1—C10—C9	1.66 (16)	C11—C12—C17—C16	−176.65 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1ⁱ	0.95	2.35	3.2139 (15)	151

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅FO₃
M_r	310.31
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	193
a, b, c (Å)	10.9714 (2), 7.51791 (14), 18.7832 (3)
β (°)	99.917 (1)
V (Å³)	1526.13 (5)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.82
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.735, 0.853
No. of measured, independent and observed [I > 2σ(I)] reflections	26625, 2789, 2566
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.109, 1.01
No. of reflections	2789
No. of parameters	211
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.15

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP (Burnett & Johnson, 1996).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1ⁱ	0.95	2.35	3.2139 (15)	151

Symmetry code: (i) x, y+1, z.

Acknowledgements

The authors would express their gratitude to Professor Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture & Technology, for his technical advice. This work was partially supported by the Mukai Science and Technology Foundation, Tokyo, Japan.

References

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