(3,6-Dimeth-oxy-2-naphth-yl)(4-fluoro-benzo-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 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 inter-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions 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 = 310.31

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.090

S = 1.02

2738 reflections

211 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.11 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: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810006859/bt5198sup1.cif

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

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

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

Rigaku R-AXIS RAPID diffractometer	2738 independent reflections
Radiation source: fine-focus sealed tube	2530 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 10.00 pixels mm-1	θmax = 68.2°, θmin = 4.5°
ω scans	h = −10→9
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −23→23
Tmin = 0.657, Tmax = 0.705	l = −11→11
26258 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)] = 0.032	H-atom parameters constrained
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0489P)2 + 0.3826P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2738 reflections	Δρmax = 0.20 e Å−3
211 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) .