(E)-2-(4-Fluoro-benzyl-idene)cyclo-octanone.

The title compound, C(15)H(17)FO, was prepared directly from the aldol condensation of cyclo-octa-none with 4-fluoro-benz-aldehyde, catalysed by Pd(Ni,Ce) in the presence of trimethyl-silyl chloride. The eight-membered ring adopts a boat-chair conformation.

Related literature

For related structures, see: Huang, Zhu & Pan (2004 ▶); Huang, Zhu, Pan & Wan (2004 ▶); Zhu & Pan (2004 ▶). For general background, see: Amal Raj & Raghathan (2002 ▶); Deli et al. (1984 ▶).

Experimental

Crystal data

C15H17FO

M = 232.29

Orthorhombic,

a = 12.0310 (2) Å

b = 8.6056 (1) Å

c = 12.2438 (2) Å

V = 1267.65 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 273 (2) K

0.20 × 0.15 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.983, T max = 0.998

10067 measured reflections

1584 independent reflections

1584 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.082

S = 1.07

1584 reflections

155 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.11 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037653/rk2112sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037653/rk2112Isup2.hkl

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

C15H17FO	F000 = 496
Mr = 232.29	Dx = 1.217 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2166 reflections
a = 12.0310 (2) Å	θ = 2.9–22.2º
b = 8.60560 (10) Å	µ = 0.08 mm−1
c = 12.2438 (2) Å	T = 273 (2) K
V = 1267.65 (3) Å3	Block, colourless
Z = 4	0.20 × 0.15 × 0.10 mm

Bruker APEXII CCD diffractometer	1584 independent reflections
Radiation source: Fine-focus sealed tube	1584 reflections with I > 2σ(I)
Monochromator: Graphite	Rint = 0.036
T = 273(2) K	θmax = 27.9º
φ and ω scans	θmin = 2.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)	h = −15→12
Tmin = 0.983, Tmax = 0.998	k = −11→10
10067 measured reflections	l = −16→13

Refinement on F2	Hydrogen site location: Geom
Least-squares matrix: Full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.037	w = 1/[σ2(Fo2) + (0.0347P)2 + 0.02P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.082	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.11 e Å−3
1584 reflections	Δρmin = −0.10 e Å−3
155 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.011 (2)
Primary atom site location: Direct	Absolute structure: Since the molecule contains only light atoms, the intensities of 946 Friedels pairs were merged.
Secondary atom site location: Difmap

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1	0.1978 (2)	1.3725 (3)	0.0997 (2)	0.0624 (7)
H1	0.1549	1.4428	0.1392	0.075*
C2	0.1992 (2)	1.3747 (3)	−0.0114 (3)	0.0623 (7)
C3	0.2606 (2)	1.2750 (3)	−0.0732 (2)	0.0592 (6)
H3	0.2605	1.2816	−0.1490	0.071*
C4	0.32327 (19)	1.1634 (2)	−0.01984 (19)	0.0518 (6)
H4	0.3655	1.0940	−0.0607	0.062*
C5	0.32435 (18)	1.1529 (2)	0.09343 (18)	0.0471 (6)
C6	0.26236 (18)	1.2618 (2)	0.1518 (2)	0.0564 (6)
H6	0.2645	1.2601	0.2277	0.068*
C7	0.39214 (17)	1.0387 (2)	0.15185 (19)	0.0495 (5)
H7	0.4307	1.0764	0.2121	0.059*
C8	0.40628 (16)	0.8869 (2)	0.13044 (17)	0.0466 (5)
C9	0.4813 (2)	0.8002 (3)	0.20544 (19)	0.0529 (6)
C10	0.4617 (2)	0.6306 (3)	0.2298 (2)	0.0654 (7)
H10A	0.3849	0.6052	0.2133	0.078*
H10B	0.4735	0.6124	0.3071	0.078*
C11	0.5378 (2)	0.5233 (3)	0.1644 (2)	0.0694 (8)
H11A	0.6138	0.5581	0.1745	0.083*
H11B	0.5323	0.4197	0.1951	0.083*
C12	0.5154 (2)	0.5126 (3)	0.0430 (2)	0.0627 (6)
H12A	0.4396	0.4768	0.0327	0.075*
H12B	0.5643	0.4345	0.0122	0.075*
C13	0.53068 (18)	0.6639 (3)	−0.0216 (2)	0.0565 (6)
H13A	0.5763	0.7339	0.0214	0.068*
H13B	0.5715	0.6403	−0.0879	0.068*
C14	0.42430 (19)	0.7491 (3)	−0.05315 (19)	0.0586 (6)
H14A	0.3820	0.6829	−0.1020	0.070*
H14B	0.4446	0.8417	−0.0937	0.070*
C15	0.34864 (16)	0.7973 (2)	0.0413 (2)	0.0534 (5)
H15A	0.2886	0.8604	0.0125	0.064*
H15B	0.3159	0.7046	0.0728	0.064*
F1	0.13754 (15)	1.48509 (16)	−0.06379 (17)	0.0991 (5)
O1	0.56001 (15)	0.86558 (19)	0.24861 (14)	0.0704 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0563 (14)	0.0496 (14)	0.081 (2)	0.0065 (11)	0.0107 (15)	−0.0091 (14)
C2	0.0545 (14)	0.0467 (14)	0.086 (2)	0.0093 (12)	−0.0095 (14)	0.0034 (13)
C3	0.0650 (16)	0.0544 (13)	0.0583 (15)	0.0011 (12)	−0.0012 (12)	0.0033 (13)
C4	0.0543 (14)	0.0440 (12)	0.0572 (15)	0.0045 (10)	0.0064 (12)	−0.0006 (11)
C5	0.0503 (14)	0.0413 (12)	0.0499 (14)	0.0000 (9)	0.0058 (12)	−0.0013 (10)
C6	0.0613 (15)	0.0497 (12)	0.0583 (14)	−0.0031 (11)	0.0086 (13)	−0.0042 (13)
C7	0.0552 (13)	0.0497 (11)	0.0437 (12)	−0.0012 (10)	0.0040 (11)	0.0004 (11)
C8	0.0446 (12)	0.0456 (11)	0.0494 (14)	−0.0003 (9)	0.0051 (11)	0.0017 (10)
C9	0.0619 (15)	0.0542 (13)	0.0426 (13)	0.0023 (12)	0.0037 (12)	0.0032 (11)
C10	0.0829 (17)	0.0545 (14)	0.0587 (16)	0.0075 (13)	0.0069 (14)	0.0140 (12)
C11	0.0798 (19)	0.0520 (13)	0.077 (2)	0.0113 (12)	−0.0010 (16)	0.0103 (13)
C12	0.0629 (14)	0.0498 (13)	0.0754 (17)	0.0080 (10)	−0.0007 (14)	−0.0058 (14)
C13	0.0572 (13)	0.0571 (13)	0.0551 (14)	0.0038 (10)	0.0045 (11)	−0.0084 (11)
C14	0.0651 (15)	0.0564 (13)	0.0543 (14)	−0.0007 (11)	−0.0112 (13)	−0.0075 (11)
C15	0.0454 (11)	0.0466 (11)	0.0682 (14)	0.0005 (9)	−0.0094 (13)	0.0010 (12)
F1	0.1013 (12)	0.0788 (9)	0.1173 (13)	0.0376 (9)	−0.0210 (11)	0.0041 (9)
O1	0.0841 (12)	0.0686 (10)	0.0583 (11)	−0.0009 (9)	−0.0200 (10)	0.0053 (8)

C1—C2	1.361 (4)	C10—C11	1.527 (3)
C1—C6	1.385 (3)	C10—H10A	0.9700
C1—H1	0.9300	C10—H10B	0.9700
C2—C3	1.361 (3)	C11—C12	1.514 (4)
C2—F1	1.365 (3)	C11—H11A	0.9700
C3—C4	1.384 (3)	C11—H11B	0.9700
C3—H3	0.9300	C12—C13	1.535 (3)
C4—C5	1.390 (3)	C12—H12A	0.9700
C4—H4	0.9300	C12—H12B	0.9700
C5—C6	1.395 (3)	C13—C14	1.524 (3)
C5—C7	1.464 (3)	C13—H13A	0.9700
C6—H6	0.9300	C13—H13B	0.9700
C7—C8	1.343 (3)	C14—C15	1.529 (3)
C7—H7	0.9300	C14—H14A	0.9700
C8—C9	1.488 (3)	C14—H14B	0.9700
C8—C15	1.506 (3)	C15—H15A	0.9700
C9—O1	1.222 (3)	C15—H15B	0.9700
C9—C10	1.508 (3)
C2—C1—C6	117.6 (2)	H10A—C10—H10B	107.8
C2—C1—H1	121.2	C12—C11—C10	116.4 (2)
C6—C1—H1	121.2	C12—C11—H11A	108.2
C1—C2—C3	123.6 (2)	C10—C11—H11A	108.2
C1—C2—F1	118.1 (3)	C12—C11—H11B	108.2
C3—C2—F1	118.2 (3)	C10—C11—H11B	108.2
C2—C3—C4	118.1 (2)	H11A—C11—H11B	107.3
C2—C3—H3	121.0	C11—C12—C13	115.7 (2)
C4—C3—H3	121.0	C11—C12—H12A	108.4
C3—C4—C5	121.4 (2)	C13—C12—H12A	108.4
C3—C4—H4	119.3	C11—C12—H12B	108.4
C5—C4—H4	119.3	C13—C12—H12B	108.4
C4—C5—C6	117.6 (2)	H12A—C12—H12B	107.4
C4—C5—C7	122.4 (2)	C14—C13—C12	115.95 (19)
C6—C5—C7	119.9 (2)	C14—C13—H13A	108.3
C1—C6—C5	121.7 (3)	C12—C13—H13A	108.3
C1—C6—H6	119.1	C14—C13—H13B	108.3
C5—C6—H6	119.1	C12—C13—H13B	108.3
C8—C7—C5	128.9 (2)	H13A—C13—H13B	107.4
C8—C7—H7	115.5	C13—C14—C15	116.02 (19)
C5—C7—H7	115.5	C13—C14—H14A	108.3
C7—C8—C9	116.4 (2)	C15—C14—H14A	108.3
C7—C8—C15	125.55 (19)	C13—C14—H14B	108.3
C9—C8—C15	118.01 (17)	C15—C14—H14B	108.3
O1—C9—C8	120.40 (19)	H14A—C14—H14B	107.4
O1—C9—C10	118.8 (2)	C8—C15—C14	114.40 (16)
C8—C9—C10	120.8 (2)	C8—C15—H15A	108.7
C9—C10—C11	112.8 (2)	C14—C15—H15A	108.7
C9—C10—H10A	109.0	C8—C15—H15B	108.7
C11—C10—H10A	109.0	C14—C15—H15B	108.7
C9—C10—H10B	109.0	H15A—C15—H15B	107.6
C11—C10—H10B	109.0
C6—C1—C2—C3	−0.2 (4)	C7—C8—C9—O1	−31.5 (3)
C6—C1—C2—F1	−178.79 (18)	C15—C8—C9—O1	151.4 (2)
C1—C2—C3—C4	1.3 (4)	C7—C8—C9—C10	148.4 (2)
F1—C2—C3—C4	179.8 (2)	C15—C8—C9—C10	−28.7 (3)
C2—C3—C4—C5	−0.2 (4)	O1—C9—C10—C11	−79.6 (3)
C3—C4—C5—C6	−1.8 (4)	C8—C9—C10—C11	100.6 (3)
C3—C4—C5—C7	−178.35 (18)	C9—C10—C11—C12	−70.2 (3)
C2—C1—C6—C5	−1.9 (4)	C10—C11—C12—C13	63.3 (3)
C4—C5—C6—C1	2.9 (3)	C11—C12—C13—C14	−102.8 (3)
C7—C5—C6—C1	179.6 (2)	C12—C13—C14—C15	58.4 (3)
C4—C5—C7—C8	−44.6 (4)	C7—C8—C15—C14	109.4 (2)
C6—C5—C7—C8	138.9 (2)	C9—C8—C15—C14	−73.8 (2)
C5—C7—C8—C9	180.0 (2)	C13—C14—C15—C8	51.9 (3)
C5—C7—C8—C15	−3.2 (4)