(2,7-Dimeth-oxy-naphthalen-1-yl)(4-fluoro-phen-yl)methanone.

In the title compound, C(19)H(15)FO(3), the dihedral angle between the naphthalene ring system and the benzene ring is 80.46 (4)°. In the crystal, mol-ecules are linked by inter-molecular 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 = 310.31

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.109

S = 1.01

2789 reflections

211 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.15 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/S1600536811018332/rz2596sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811018332/rz2596Isup3.cml

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

C19H15FO3	F(000) = 648
Mr = 310.31	Dx = 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

Rigaku R-AXIS RAPID diffractometer	2789 independent reflections
Radiation source: fine-focus sealed tube	2566 reflections with I > 2σ(I)
graphite	Rint = 0.036
Detector resolution: 10.00 pixels mm-1	θmax = 68.3°, θmin = 4.4°
ω scans	h = −13→13
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −9→9
Tmin = 0.735, Tmax = 0.853	l = −22→22
26625 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-atom parameters constrained
wR(F2) = 0.109	w = 1/[σ2(Fo2) + (0.0726P)2 + 0.253P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
2789 reflections	Δρmax = 0.23 e Å−3
211 parameters	Δρmin = −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)

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	0.88989 (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*

	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)

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)

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

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) .