6-Fluoro-indan-1-one.

The title compound, C9H7FO, crystallizes with two independent mol-ecules in the asymmetric unit, in which corresponding bond lengths are the same within experimental error. The five-membered ring in each molecule is almost planar, with r.m.s. deviations of 0.016 and 0.029 Å. In the crystal, mol-ecules form sheets parallel to (1 0 0) via C-H⋯O and C-H⋯F inter-actions with F⋯F contacts [3.1788 (16) and 3.2490 (16) Å] between the sheets.

Related literature

For the synthesis of 6-fluoroindan-1-one, see: Cui et al. (2004 ▶) and for its use in synthesis, see: Musso et al. (2003 ▶); Ślusarczyk et al. (2007 ▶); Yin et al. (2013 ▶). For the structure of the parent comound, 1-indanone, see: Morin et al. (1974 ▶) and Ruiz et al. (2004 ▶), the later containing a detailed analysis of the hydrogen bonding. For a related isomeric structure, 5-fluoroindan-1-one, see: Garcia et al. (1995 ▶). For more information on C—H⋯X inter­actions, see Desiraju & Steiner (1999 ▶) and on fluorine–fluorine inter­actions in the solid state, see: Baker et al. (2012 ▶). For van der Waals radii, see: Bondi (1964 ▶).

Experimental

Crystal data

C9H7FO

M = 150.15

Monoclinic,

a = 7.1900 (4) Å

b = 12.4811 (6) Å

c = 15.8685 (8) Å

β = 99.453 (1)°

V = 1404.69 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 125 K

0.37 × 0.26 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker 2007 ▶) T min = 0.91, T max = 1.00

22840 measured reflections

4298 independent reflections

3345 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.121

S = 1.03

4298 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, OLEX2 (Dolomanov et al., 2009 ▶) and Mercury (Macrae et al., 2006 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814015049/kj2241sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814015049/kj2241Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814015049/kj2241Isup3.cml

CCDC reference: 1010372

Additional supporting information: crystallographic information; 3D view; checkCIF report

C9H7FO	F(000) = 624
Mr = 150.15	Dx = 1.420 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.1900 (4) Å	Cell parameters from 9796 reflections
b = 12.4811 (6) Å	θ = 2.6–30.5°
c = 15.8685 (8) Å	µ = 0.11 mm−1
β = 99.453 (1)°	T = 125 K
V = 1404.69 (13) Å3	Plate, colourless
Z = 8	0.37 × 0.26 × 0.04 mm

Bruker APEXII CCD diffractometer	4298 independent reflections
Radiation source: fine-focus sealed tube	3345 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 8.3333 pixels mm-1	θmax = 30.5°, θmin = 2.1°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker 2007)	k = −17→17
Tmin = 0.91, Tmax = 1.00	l = −22→22
22840 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0654P)2 + 0.2949P] where P = (Fo2 + 2Fc2)/3
4298 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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	0.57983 (11)	0.61035 (7)	0.04096 (4)	0.03306 (19)
F2	0.08173 (11)	0.60328 (6)	0.05655 (4)	0.03227 (19)
O1	0.58188 (12)	0.56668 (7)	0.37571 (5)	0.02425 (18)
O2	0.10060 (13)	0.64991 (7)	0.39289 (5)	0.0290 (2)
C1	0.63562 (14)	0.65257 (8)	0.35245 (6)	0.01661 (19)
C2	0.69797 (16)	0.74848 (9)	0.40858 (7)	0.0209 (2)
H2A	0.8032	0.7285	0.4543	0.025*
H2B	0.5922	0.7756	0.4354	0.025*
C3	0.76215 (15)	0.83443 (8)	0.35003 (7)	0.0198 (2)
H3A	0.6904	0.9017	0.3526	0.024*
H3B	0.8983	0.8498	0.3666	0.024*
C4	0.72154 (14)	0.78578 (8)	0.26152 (7)	0.0170 (2)
C5	0.74667 (15)	0.83033 (9)	0.18320 (7)	0.0217 (2)
H5	0.7957	0.9007	0.1806	0.026*
C6	0.69871 (16)	0.76990 (10)	0.10921 (7)	0.0238 (2)
H6	0.7148	0.7986	0.0555	0.029*
C7	0.62701 (15)	0.66714 (9)	0.11444 (7)	0.0218 (2)
C8	0.60039 (14)	0.62037 (9)	0.19016 (7)	0.0188 (2)
H8	0.5513	0.5499	0.1923	0.023*
C9	0.64971 (14)	0.68253 (8)	0.26346 (6)	0.01567 (19)
C10	0.14218 (14)	0.56199 (9)	0.36835 (6)	0.0184 (2)
C11	0.19726 (16)	0.46437 (9)	0.42394 (7)	0.0214 (2)
H11A	0.0886	0.4385	0.4493	0.026*
H11B	0.3016	0.4821	0.4707	0.026*
C12	0.26009 (15)	0.37845 (9)	0.36496 (7)	0.0195 (2)
H12A	0.3964	0.363	0.381	0.023*
H12B	0.1884	0.3112	0.3678	0.023*
C13	0.21781 (14)	0.42705 (8)	0.27662 (6)	0.01607 (19)
C14	0.24187 (15)	0.38210 (9)	0.19853 (7)	0.0195 (2)
H14	0.2889	0.3112	0.196	0.023*
C15	0.19576 (15)	0.44297 (9)	0.12451 (7)	0.0212 (2)
H15	0.2117	0.4142	0.0707	0.025*
C16	0.12627 (15)	0.54614 (9)	0.13004 (6)	0.0204 (2)
C17	0.10060 (15)	0.59323 (8)	0.20572 (7)	0.0189 (2)
H17	0.0525	0.6639	0.2079	0.023*
C18	0.14943 (14)	0.53097 (8)	0.27900 (6)	0.01578 (19)

	U11	U22	U33	U12	U13	U23
F1	0.0391 (4)	0.0439 (5)	0.0154 (3)	0.0011 (3)	0.0024 (3)	−0.0091 (3)
F2	0.0434 (4)	0.0365 (4)	0.0151 (3)	−0.0035 (3)	−0.0006 (3)	0.0100 (3)
O1	0.0307 (4)	0.0212 (4)	0.0204 (4)	−0.0055 (3)	0.0027 (3)	0.0036 (3)
O2	0.0401 (5)	0.0244 (4)	0.0227 (4)	0.0082 (4)	0.0053 (3)	−0.0045 (3)
C1	0.0165 (4)	0.0173 (5)	0.0158 (4)	0.0016 (4)	0.0022 (3)	−0.0003 (3)
C2	0.0274 (5)	0.0192 (5)	0.0165 (5)	−0.0002 (4)	0.0044 (4)	−0.0029 (4)
C3	0.0217 (5)	0.0158 (5)	0.0220 (5)	−0.0010 (4)	0.0041 (4)	−0.0034 (4)
C4	0.0163 (4)	0.0160 (5)	0.0192 (5)	0.0021 (3)	0.0039 (4)	0.0005 (4)
C5	0.0210 (5)	0.0195 (5)	0.0254 (5)	0.0013 (4)	0.0067 (4)	0.0051 (4)
C6	0.0224 (5)	0.0307 (6)	0.0193 (5)	0.0050 (4)	0.0070 (4)	0.0061 (4)
C7	0.0214 (5)	0.0287 (6)	0.0149 (5)	0.0047 (4)	0.0018 (4)	−0.0040 (4)
C8	0.0184 (5)	0.0195 (5)	0.0179 (5)	0.0009 (4)	0.0013 (4)	−0.0024 (4)
C9	0.0166 (4)	0.0154 (4)	0.0151 (4)	0.0010 (3)	0.0027 (3)	−0.0008 (3)
C10	0.0187 (5)	0.0205 (5)	0.0159 (4)	0.0010 (4)	0.0026 (3)	−0.0004 (4)
C11	0.0262 (5)	0.0234 (5)	0.0147 (4)	0.0006 (4)	0.0037 (4)	0.0026 (4)
C12	0.0214 (5)	0.0191 (5)	0.0182 (5)	0.0026 (4)	0.0040 (4)	0.0048 (4)
C13	0.0156 (4)	0.0166 (5)	0.0160 (4)	−0.0011 (3)	0.0027 (3)	0.0012 (3)
C14	0.0189 (5)	0.0195 (5)	0.0206 (5)	−0.0004 (4)	0.0044 (4)	−0.0027 (4)
C15	0.0212 (5)	0.0270 (5)	0.0159 (5)	−0.0047 (4)	0.0045 (4)	−0.0039 (4)
C16	0.0209 (5)	0.0258 (5)	0.0135 (4)	−0.0047 (4)	0.0003 (4)	0.0049 (4)
C17	0.0200 (5)	0.0178 (5)	0.0178 (5)	0.0000 (4)	−0.0002 (4)	0.0029 (4)
C18	0.0157 (4)	0.0169 (5)	0.0145 (4)	−0.0007 (3)	0.0019 (3)	0.0002 (3)

F1—C7	1.3592 (12)	C7—C8	1.3772 (15)
F1—F1i	3.1788 (16)	C8—C9	1.3947 (14)
F2—C16	1.3596 (11)	C8—H8	0.95
F2—F2ii	3.2490 (16)	C10—C18	1.4790 (14)
O1—C1	1.2172 (13)	C10—C11	1.5181 (15)
O2—C10	1.2179 (13)	C11—C12	1.5392 (15)
C1—C9	1.4802 (14)	C11—H11A	0.99
C1—C2	1.5152 (14)	C11—H11B	0.99
C2—C3	1.5387 (15)	C12—C13	1.5118 (14)
C2—H2A	0.99	C12—H12A	0.99
C2—H2B	0.99	C12—H12B	0.99
C3—C4	1.5140 (14)	C13—C18	1.3898 (14)
C3—H3A	0.99	C13—C14	1.3967 (14)
C3—H3B	0.99	C14—C15	1.3924 (15)
C4—C9	1.3905 (14)	C14—H14	0.95
C4—C5	1.4000 (14)	C15—C16	1.3892 (16)
C5—C6	1.3904 (16)	C15—H15	0.95
C5—H5	0.95	C16—C17	1.3764 (15)
C6—C7	1.3898 (17)	C17—C18	1.3946 (14)
C6—H6	0.95	C17—H17	0.95
F1···F1i	3.1788 (16)	F2···F2ii	3.2490 (16)
C7—F1—F1i	145.61 (8)	C8—C9—C1	127.39 (9)
C16—F2—F2ii	94.04 (6)	O2—C10—C18	126.26 (10)
O1—C1—C9	125.92 (9)	O2—C10—C11	126.27 (10)
O1—C1—C2	126.55 (9)	C18—C10—C11	107.46 (9)
C9—C1—C2	107.53 (8)	C10—C11—C12	106.29 (8)
C1—C2—C3	106.56 (8)	C10—C11—H11A	110.5
C1—C2—H2A	110.4	C12—C11—H11A	110.5
C3—C2—H2A	110.4	C10—C11—H11B	110.5
C1—C2—H2B	110.4	C12—C11—H11B	110.5
C3—C2—H2B	110.4	H11A—C11—H11B	108.7
H2A—C2—H2B	108.6	C13—C12—C11	104.47 (8)
C4—C3—C2	104.43 (8)	C13—C12—H12A	110.9
C4—C3—H3A	110.9	C11—C12—H12A	110.9
C2—C3—H3A	110.9	C13—C12—H12B	110.9
C4—C3—H3B	110.9	C11—C12—H12B	110.9
C2—C3—H3B	110.9	H12A—C12—H12B	108.9
H3A—C3—H3B	108.9	C18—C13—C14	119.66 (9)
C9—C4—C5	119.36 (10)	C18—C13—C12	111.56 (9)
C9—C4—C3	111.52 (9)	C14—C13—C12	128.76 (10)
C5—C4—C3	129.12 (10)	C15—C14—C13	118.83 (10)
C6—C5—C4	118.94 (10)	C15—C14—H14	120.6
C6—C5—H5	120.5	C13—C14—H14	120.6
C4—C5—H5	120.5	C16—C15—C14	119.39 (9)
C7—C6—C5	119.55 (10)	C16—C15—H15	120.3
C7—C6—H6	120.2	C14—C15—H15	120.3
C5—C6—H6	120.2	F2—C16—C17	118.56 (10)
F1—C7—C8	118.46 (10)	F2—C16—C15	117.94 (9)
F1—C7—C6	118.21 (10)	C17—C16—C15	123.51 (9)
C8—C7—C6	123.32 (10)	C16—C17—C18	115.98 (10)
C7—C8—C9	116.05 (10)	C16—C17—H17	122.0
C7—C8—H8	122.0	C18—C17—H17	122.0
C9—C8—H8	122.0	C13—C18—C17	122.62 (9)
C4—C9—C8	122.78 (9)	C13—C18—C10	109.79 (9)
C4—C9—C1	109.83 (9)	C17—C18—C10	127.58 (10)
O2—C10—C18—C17	−3.94 (18)	C3—C4—C5—C6	−179.93 (10)
O2—C10—C18—C13	174.94 (11)	C2—C3—C4—C9	−2.21 (11)
O2—C10—C11—C12	−173.07 (11)	C2—C3—C4—C5	177.79 (10)
O1—C1—C9—C8	1.81 (17)	C2—C1—C9—C8	−177.56 (10)
O1—C1—C9—C4	−178.32 (10)	C2—C1—C9—C4	2.31 (11)
O1—C1—C2—C3	177.04 (10)	C1—C2—C3—C4	3.48 (11)
F2ii—F2—C16—C17	−142.91 (9)	C18—C13—C14—C15	−0.21 (15)
F2ii—F2—C16—C15	37.18 (10)	C18—C10—C11—C12	6.57 (11)
F2—C16—C17—C18	−179.74 (9)	C16—C17—C18—C13	−0.78 (15)
F1i—F1—C7—C8	−1.14 (19)	C16—C17—C18—C10	177.97 (10)
F1i—F1—C7—C6	179.25 (9)	C15—C16—C17—C18	0.17 (16)
F1—C7—C8—C9	−179.49 (9)	C14—C15—C16—F2	−179.69 (9)
C9—C4—C5—C6	0.07 (15)	C14—C15—C16—C17	0.40 (16)
C9—C1—C2—C3	−3.60 (11)	C14—C13—C18—C17	0.82 (15)
C7—C8—C9—C4	0.06 (15)	C14—C13—C18—C10	−178.13 (9)
C7—C8—C9—C1	179.91 (10)	C13—C14—C15—C16	−0.38 (15)
C6—C7—C8—C9	0.10 (16)	C12—C13—C18—C17	179.76 (9)
C5—C6—C7—F1	179.42 (9)	C12—C13—C18—C10	0.81 (12)
C5—C6—C7—C8	−0.16 (17)	C12—C13—C14—C15	−178.95 (10)
C5—C4—C9—C8	−0.14 (15)	C11—C12—C13—C18	3.30 (11)
C5—C4—C9—C1	179.98 (9)	C11—C12—C13—C14	−177.87 (10)
C4—C5—C6—C7	0.07 (16)	C11—C10—C18—C17	176.42 (10)
C3—C4—C9—C8	179.86 (9)	C11—C10—C18—C13	−4.70 (12)
C3—C4—C9—C1	−0.02 (12)	C10—C11—C12—C13	−5.93 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1iii	0.95	2.47	3.3873 (14)	161
C14—H14···O2iv	0.95	2.65	3.5107 (14)	150
C2—H2B···F2v	0.99	2.46	3.2062 (13)	132
C6—H6···O2vi	0.95	2.65	3.5338 (14)	154
C11—H11B···O1vii	0.99	2.52	3.3348 (13)	140
C15—H15···F1i	0.95	2.52	3.3664 (13)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1i	0.95	2.47	3.3873 (14)	161
C14—H14⋯O2ii	0.95	2.65	3.5107 (14)	150
C2—H2B⋯F2iii	0.99	2.46	3.2062 (13)	132
C6—H6⋯O2iv	0.95	2.65	3.5338 (14)	154
C11—H11B⋯O1v	0.99	2.52	3.3348 (13)	140
C15—H15⋯F1vi	0.95	2.52	3.3664 (13)	148

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .