(E)-2-(2-Fluoro­benzyl­idene)­cyclo­octanone

The title compound, C₁₅H₁₇FO, was synthesized directly from the condensation of cyclo­octanone with 2-fluorobenzaldehyde, catalysed effectively by palladium in the presence of tri­methyl­silyl chloride (TMSCl). The structure contains a boat–chair eight-membered ring and a benzene ring. The packing of the mol­ecules in the crystal structure is mainly due to C—H...π interactions and C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 287 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.032
• wR factor = 0.073
• Data-to-parameter ratio = 10.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT480_ALERT_4_B Long H...A H-Bond Reported H4A    ..  CGP     ..       2.85 Ang.
PLAT480_ALERT_4_B Long H...A H-Bond Reported H4B    ..  CGP     ..       2.90 Ang.

Alert level C
PLAT481_ALERT_4_C Long D...A H-Bond Reported C4     ..  CGP     ..       3.74 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C4     ..  CGP     ..       3.83 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.85
           From the CIF: _reflns_number_total               1560
           Count of symmetry unique reflns         1560
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(I)

Crystal data

C15H17FO	Dx = 1.233 Mg m^−3
Mr = 232.29	Melting point: 465–466 K K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 39 reflections
a = 12.291 (1) Å	θ = 3.0–14.6°
b = 8.294 (1) Å	µ = 0.09 mm^−1
c = 12.273 (1) Å	T = 287 K
V = 1251.2 (2) Å^3	Block, colorless
Z = 4	0.50 × 0.50 × 0.46 mm
F(000) = 496

Data collection

Siemens P4 diffractometer	Rint = 0.009
Radiation source: normal-focus sealed tube	θmax = 27.9°, θmin = 3.0°
Graphite monochromator	h = −1→16
ω scans	k = 0→10
1904 measured reflections	l = 0→16
1560 independent reflections	3 standard reflections every 97 reflections
1207 reflections with I > 2σ(I)	intensity decay: 2.7%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.073	w = 1/[σ^2(Fo^2) + (0.0429P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.94	(Δ/σ)max < 0.001
1560 reflections	Δρmax = 0.11 e Å^−3
154 parameters	Δρmin = −0.10 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.033 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
F1	0.74470 (11)	0.76983 (16)	0.40459 (10)	0.0722 (4)
O1	0.46008 (14)	0.37243 (18)	0.41115 (12)	0.0684 (5)
C1	0.52979 (17)	0.3016 (2)	0.35914 (16)	0.0461 (4)
C2	0.5466 (2)	0.1227 (2)	0.37770 (17)	0.0573 (6)
H2A	0.5406	0.1003	0.4550	0.069*
H2B	0.6196	0.0938	0.3549	0.069*
C3	0.4650 (2)	0.0181 (3)	0.31624 (19)	0.0621 (6)
H3A	0.4708	−0.0913	0.3437	0.075*
H3B	0.3924	0.0562	0.3334	0.075*
C4	0.47646 (18)	0.0126 (2)	0.19302 (18)	0.0546 (5)
H4A	0.4245	−0.0646	0.1646	0.066*
H4B	0.5487	−0.0268	0.1755	0.066*
C5	0.45920 (16)	0.1737 (2)	0.13445 (16)	0.0485 (5)
H5A	0.4126	0.1550	0.0720	0.058*
H5B	0.4206	0.2456	0.1834	0.058*
C6	0.56082 (18)	0.2586 (2)	0.09556 (16)	0.0498 (5)
H6A	0.5395	0.3585	0.0605	0.060*
H6B	0.5955	0.1917	0.0408	0.060*
C7	0.64514 (13)	0.2979 (2)	0.18409 (17)	0.0451 (4)
H7A	0.6763	0.1979	0.2107	0.054*
H7B	0.7034	0.3606	0.1519	0.054*
C8	0.59863 (13)	0.3901 (2)	0.27899 (14)	0.0382 (4)
C9	0.61667 (15)	0.5459 (2)	0.30104 (15)	0.0428 (4)
H9	0.5837	0.5854	0.3638	0.051*
C10	0.68198 (15)	0.6627 (2)	0.23886 (15)	0.0407 (4)
C11	0.68246 (16)	0.6746 (2)	0.12592 (16)	0.0475 (5)
H11	0.6400	0.6041	0.0852	0.057*
C12	0.74456 (19)	0.7889 (3)	0.0728 (2)	0.0563 (6)
H12	0.7431	0.7949	−0.0028	0.068*
C13	0.8086 (2)	0.8937 (3)	0.1311 (2)	0.0644 (6)
H13	0.8513	0.9690	0.0948	0.077*
C14	0.80958 (18)	0.8877 (3)	0.2435 (2)	0.0595 (6)
H14	0.8523	0.9585	0.2838	0.071*
C15	0.74594 (17)	0.7745 (2)	0.29407 (17)	0.0492 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0863 (9)	0.0736 (9)	0.0568 (8)	−0.0067 (7)	−0.0207 (7)	−0.0137 (7)
O1	0.0921 (11)	0.0618 (9)	0.0514 (9)	0.0018 (8)	0.0305 (9)	0.0017 (8)
C1	0.0590 (11)	0.0454 (10)	0.0341 (9)	−0.0037 (10)	−0.0048 (10)	0.0026 (8)
C2	0.0797 (14)	0.0466 (11)	0.0456 (12)	−0.0055 (11)	−0.0047 (11)	0.0126 (9)
C3	0.0805 (16)	0.0475 (11)	0.0583 (14)	−0.0167 (11)	0.0069 (13)	0.0081 (10)
C4	0.0589 (12)	0.0474 (11)	0.0576 (13)	−0.0115 (9)	0.0052 (11)	−0.0044 (10)
C5	0.0484 (10)	0.0531 (11)	0.0441 (9)	−0.0033 (10)	−0.0037 (9)	−0.0068 (9)
C6	0.0616 (12)	0.0496 (10)	0.0383 (9)	−0.0050 (9)	0.0111 (9)	−0.0057 (9)
C7	0.0390 (8)	0.0396 (9)	0.0568 (11)	0.0008 (8)	0.0117 (10)	0.0020 (10)
C8	0.0365 (9)	0.0391 (9)	0.0389 (9)	0.0032 (7)	−0.0060 (8)	0.0015 (8)
C9	0.0486 (10)	0.0433 (9)	0.0364 (9)	0.0030 (9)	−0.0056 (8)	−0.0005 (8)
C10	0.0405 (11)	0.0335 (10)	0.0482 (11)	0.0041 (8)	−0.0065 (9)	−0.0017 (8)
C11	0.0477 (11)	0.0432 (11)	0.0516 (12)	−0.0031 (10)	−0.0063 (10)	0.0019 (9)
C12	0.0577 (14)	0.0516 (13)	0.0595 (13)	−0.0006 (11)	0.0043 (11)	0.0084 (10)
C13	0.0563 (13)	0.0446 (12)	0.0923 (19)	−0.0061 (11)	0.0123 (13)	0.0042 (13)
C14	0.0488 (12)	0.0428 (12)	0.0870 (19)	−0.0074 (10)	−0.0085 (12)	−0.0107 (13)
C15	0.0484 (11)	0.0417 (11)	0.0575 (13)	0.0043 (9)	−0.0120 (10)	−0.0069 (10)

Geometric parameters (Å, º)

F1—C15	1.357 (2)	C6—H6B	0.97
O1—C1	1.219 (2)	C7—C8	1.506 (3)
C1—C8	1.491 (3)	C7—H7A	0.97
C1—C2	1.515 (3)	C7—H7B	0.97
C2—C3	1.526 (3)	C8—C9	1.339 (2)
C2—H2A	0.97	C9—C10	1.472 (3)
C2—H2B	0.97	C9—H9	0.93
C3—C4	1.520 (3)	C10—C11	1.390 (2)
C3—H3A	0.97	C10—C15	1.391 (3)
C3—H3B	0.97	C11—C12	1.380 (3)
C4—C5	1.532 (3)	C11—H11	0.93
C4—H4A	0.97	C12—C13	1.374 (3)
C4—H4B	0.97	C12—H12	0.93
C5—C6	1.511 (3)	C13—C14	1.380 (3)
C5—H5A	0.97	C13—H13	0.93
C5—H5B	0.97	C14—C15	1.370 (3)
C6—C7	1.537 (3)	C14—H14	0.93
C6—H6A	0.97
O1—C1—C8	120.46 (17)	H6A—C6—H6B	107.4
O1—C1—C2	119.27 (19)	C8—C7—C6	113.48 (14)
C8—C1—C2	120.27 (18)	C8—C7—H7A	108.9
C1—C2—C3	113.17 (18)	C6—C7—H7A	108.9
C1—C2—H2A	108.9	C8—C7—H7B	108.9
C3—C2—H2A	108.9	C6—C7—H7B	108.9
C1—C2—H2B	108.9	H7A—C7—H7B	107.7
C3—C2—H2B	108.9	C9—C8—C1	115.84 (17)
H2A—C2—H2B	107.8	C9—C8—C7	125.70 (17)
C4—C3—C2	116.59 (19)	C1—C8—C7	118.41 (15)
C4—C3—H3A	108.1	C8—C9—C10	128.40 (17)
C2—C3—H3A	108.1	C8—C9—H9	115.8
C4—C3—H3B	108.1	C10—C9—H9	115.8
C2—C3—H3B	108.1	C11—C10—C15	115.85 (19)
H3A—C3—H3B	107.3	C11—C10—C9	124.50 (18)
C3—C4—C5	115.37 (17)	C15—C10—C9	119.62 (17)
C3—C4—H4A	108.4	C12—C11—C10	121.5 (2)
C5—C4—H4A	108.4	C12—C11—H11	119.3
C3—C4—H4B	108.4	C10—C11—H11	119.3
C5—C4—H4B	108.4	C13—C12—C11	120.4 (2)
H4A—C4—H4B	107.5	C13—C12—H12	119.8
C6—C5—C4	116.11 (18)	C11—C12—H12	119.8
C6—C5—H5A	108.3	C12—C13—C14	120.2 (2)
C4—C5—H5A	108.3	C12—C13—H13	119.9
C6—C5—H5B	108.3	C14—C13—H13	119.9
C4—C5—H5B	108.3	C15—C14—C13	118.2 (2)
H5A—C5—H5B	107.4	C15—C14—H14	120.9
C5—C6—C7	115.65 (16)	C13—C14—H14	120.9
C5—C6—H6A	108.4	F1—C15—C14	118.6 (2)
C7—C6—H6A	108.4	F1—C15—C10	117.48 (19)
C5—C6—H6B	108.4	C14—C15—C10	123.9 (2)
C7—C6—H6B	108.4
O1—C1—C2—C3	81.3 (2)	C7—C8—C9—C10	1.6 (3)
C8—C1—C2—C3	−99.3 (2)	C8—C9—C10—C11	41.5 (3)
C1—C2—C3—C4	69.8 (3)	C8—C9—C10—C15	−140.8 (2)
C2—C3—C4—C5	−63.1 (3)	C15—C10—C11—C12	1.2 (3)
C3—C4—C5—C6	103.5 (2)	C9—C10—C11—C12	179.01 (17)
C4—C5—C6—C7	−57.8 (2)	C10—C11—C12—C13	0.5 (3)
C5—C6—C7—C8	−53.3 (2)	C11—C12—C13—C14	−1.3 (4)
O1—C1—C8—C9	29.4 (3)	C12—C13—C14—C15	0.4 (4)
C2—C1—C8—C9	−149.91 (18)	C13—C14—C15—F1	−178.7 (2)
O1—C1—C8—C7	−152.93 (19)	C13—C14—C15—C10	1.4 (4)
C2—C1—C8—C7	27.7 (2)	C11—C10—C15—F1	177.92 (18)
C6—C7—C8—C9	−107.7 (2)	C9—C10—C15—F1	0.0 (3)
C6—C7—C8—C1	74.9 (2)	C11—C10—C15—C14	−2.2 (3)
C1—C8—C9—C10	179.00 (17)	C9—C10—C15—C14	179.88 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1^i	0.93	2.47	3.189 (3)	134
C14—H14···O1^ii	0.93	2.48	3.408 (3)	173
C4—H4A···CgP^iii	0.97	2.85	3.738 (3)	153
C4—H4B···CgP^iv	0.97	2.90	3.829 (2)	160

Symmetry codes: (i) −x+1, −y+1, z−1/2; (ii) x+1/2, −y+3/2, z; (iii) x−1/2, −y+3/2, z; (iv) x, y−1, z.