(E)-2-[4-(Trifluoro-meth-oxy)benzyl-idene]indan-1-one.

In the title compound, C(17)H(11)F(3)O(2), the dihydro-indene ring is approximately planar with a maximum deviation of 0.024 (2) Å and makes a dihedral angle of 3.17 (8) Å with the adjacent benzene ring. In the crystal, mol-ecules are inter-connected by C-H⋯O inter-actions, forming an infinite chain along the c axis.

Related literature

For the biological background to dihydro­indeno and heterocyclic derivatives, see: Dinges et al. (2006 ▶); Garton et al. (2006 ▶); Lin et al. (1997 ▶); Hsieh et al. (1998 ▶); Ko et al. (2003 ▶). For a related structure, see: Ali et al. (2011 ▶). For standard bond lengths, see: Allen et al. (1987 ▶) For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C17H11F3O2

M = 304.26

Monoclinic,

a = 15.2216 (4) Å

b = 14.6734 (4) Å

c = 6.1463 (1) Å

β = 95.872 (1)°

V = 1365.59 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.38 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.955, T max = 0.978

27814 measured reflections

4043 independent reflections

3389 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.181

S = 1.11

4043 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.87 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811028698/sj5181sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028698/sj5181Isup2.hkl

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

C17H11F3O2	F(000) = 624
Mr = 304.26	Dx = 1.480 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9932 reflections
a = 15.2216 (4) Å	θ = 2.7–30.0°
b = 14.6734 (4) Å	µ = 0.12 mm−1
c = 6.1463 (1) Å	T = 100 K
β = 95.872 (1)°	Block, light-yellow
V = 1365.59 (6) Å3	0.38 × 0.20 × 0.18 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	4043 independent reflections
Radiation source: fine-focus sealed tube	3389 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 30.2°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −21→21
Tmin = 0.955, Tmax = 0.978	k = −19→20
27814 measured reflections	l = −8→8

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0634P)2 + 1.8592P] where P = (Fo2 + 2Fc2)/3
4043 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.87 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.40870 (11)	0.43026 (14)	0.4881 (3)	0.0493 (5)
F2	0.47465 (10)	0.43584 (13)	0.1983 (3)	0.0481 (4)
F3	0.51278 (10)	0.33503 (13)	0.4426 (3)	0.0467 (4)
O1	−0.10593 (11)	0.45341 (11)	−0.4450 (2)	0.0277 (3)
O2	0.38837 (11)	0.31658 (12)	0.2471 (3)	0.0315 (4)
C1	−0.06329 (13)	0.35420 (13)	0.0949 (3)	0.0211 (4)
H1A	−0.0435	0.2906	0.1220	0.025*
H1B	−0.0424	0.3919	0.2234	0.025*
C2	−0.16251 (14)	0.35906 (13)	0.0484 (3)	0.0205 (4)
C3	−0.22701 (14)	0.33207 (14)	0.1806 (3)	0.0245 (4)
H3A	−0.2111	0.3077	0.3224	0.029*
C4	−0.31497 (15)	0.34167 (16)	0.1000 (4)	0.0294 (5)
H4A	−0.3595	0.3233	0.1883	0.035*
C5	−0.33995 (15)	0.37768 (16)	−0.1085 (4)	0.0287 (4)
H5A	−0.4007	0.3834	−0.1596	0.034*
C6	−0.27604 (14)	0.40491 (14)	−0.2400 (3)	0.0244 (4)
H6A	−0.2921	0.4295	−0.3815	0.029*
C7	−0.18764 (13)	0.39517 (13)	−0.1592 (3)	0.0199 (4)
C8	−0.10851 (14)	0.41903 (13)	−0.2650 (3)	0.0217 (4)
C9	−0.02974 (15)	0.39174 (14)	−0.1129 (3)	0.0236 (4)
C10	0.05182 (15)	0.40510 (14)	−0.1712 (3)	0.0238 (4)
H10A	0.0541	0.4300	−0.3132	0.029*
C11	0.13779 (14)	0.38722 (14)	−0.0497 (3)	0.0231 (4)
C12	0.21341 (14)	0.40795 (14)	−0.1522 (3)	0.0229 (4)
H12A	0.2071	0.4368	−0.2913	0.027*
C13	0.29726 (14)	0.38732 (14)	−0.0553 (3)	0.0245 (4)
H13A	0.3481	0.3999	−0.1280	0.029*
C14	0.30495 (14)	0.34785 (14)	0.1510 (3)	0.0231 (4)
C15	0.23247 (14)	0.32961 (14)	0.2623 (3)	0.0232 (4)
H15A	0.2398	0.3041	0.4051	0.028*
C16	0.14908 (14)	0.34919 (14)	0.1619 (3)	0.0247 (4)
H16A	0.0987	0.3368	0.2366	0.030*
C17	0.44420 (15)	0.37880 (19)	0.3410 (4)	0.0334 (5)

	U11	U22	U33	U12	U13	U23
F1	0.0378 (9)	0.0719 (12)	0.0369 (8)	0.0042 (8)	−0.0022 (6)	−0.0208 (8)
F2	0.0344 (8)	0.0604 (11)	0.0489 (9)	−0.0086 (7)	0.0013 (7)	0.0168 (8)
F3	0.0275 (7)	0.0728 (12)	0.0387 (8)	0.0091 (7)	−0.0019 (6)	0.0124 (8)
O1	0.0325 (8)	0.0316 (8)	0.0196 (7)	−0.0001 (6)	0.0050 (6)	0.0053 (6)
O2	0.0285 (8)	0.0346 (9)	0.0309 (8)	0.0073 (7)	0.0000 (6)	0.0027 (6)
C1	0.0264 (10)	0.0186 (9)	0.0186 (8)	−0.0006 (7)	0.0030 (7)	0.0032 (6)
C2	0.0271 (10)	0.0157 (8)	0.0188 (8)	0.0003 (7)	0.0039 (7)	−0.0003 (6)
C3	0.0305 (11)	0.0230 (9)	0.0211 (9)	0.0009 (8)	0.0076 (7)	0.0024 (7)
C4	0.0296 (11)	0.0299 (11)	0.0302 (11)	0.0011 (9)	0.0110 (8)	0.0025 (8)
C5	0.0262 (10)	0.0294 (11)	0.0306 (11)	0.0015 (8)	0.0035 (8)	0.0004 (8)
C6	0.0276 (10)	0.0238 (9)	0.0218 (9)	0.0018 (8)	0.0019 (7)	0.0002 (7)
C7	0.0261 (10)	0.0160 (8)	0.0178 (8)	−0.0006 (7)	0.0042 (7)	−0.0007 (6)
C8	0.0271 (10)	0.0192 (9)	0.0192 (8)	0.0002 (7)	0.0037 (7)	0.0014 (6)
C9	0.0331 (11)	0.0198 (9)	0.0183 (8)	0.0003 (8)	0.0040 (7)	0.0004 (7)
C10	0.0327 (11)	0.0208 (9)	0.0184 (8)	−0.0006 (8)	0.0043 (7)	−0.0009 (7)
C11	0.0285 (10)	0.0216 (9)	0.0194 (9)	−0.0007 (8)	0.0029 (7)	0.0024 (7)
C12	0.0300 (10)	0.0213 (9)	0.0173 (8)	−0.0030 (8)	0.0023 (7)	0.0006 (7)
C13	0.0281 (10)	0.0252 (10)	0.0208 (9)	0.0004 (8)	0.0050 (7)	−0.0010 (7)
C14	0.0271 (10)	0.0201 (9)	0.0214 (9)	0.0029 (7)	−0.0013 (7)	−0.0009 (7)
C15	0.0310 (10)	0.0207 (9)	0.0175 (8)	0.0004 (8)	0.0011 (7)	0.0014 (7)
C16	0.0272 (10)	0.0257 (10)	0.0214 (9)	−0.0010 (8)	0.0036 (7)	0.0057 (7)
C17	0.0248 (11)	0.0483 (14)	0.0268 (10)	0.0028 (10)	0.0014 (8)	0.0033 (9)

F1—C17	1.334 (3)	C6—C7	1.393 (3)
F2—C17	1.330 (3)	C6—H6A	0.9500
F3—C17	1.326 (3)	C7—C8	1.469 (3)
O1—C8	1.220 (2)	C8—C9	1.497 (3)
O2—C17	1.337 (3)	C9—C10	1.341 (3)
O2—C14	1.421 (2)	C10—C11	1.463 (3)
C1—C2	1.510 (3)	C10—H10A	0.9500
C1—C9	1.526 (3)	C11—C12	1.401 (3)
C1—H1A	0.9900	C11—C16	1.409 (3)
C1—H1B	0.9900	C12—C13	1.386 (3)
C2—C3	1.395 (3)	C12—H12A	0.9500
C2—C7	1.398 (3)	C13—C14	1.388 (3)
C3—C4	1.387 (3)	C13—H13A	0.9500
C3—H3A	0.9500	C14—C15	1.382 (3)
C4—C5	1.402 (3)	C15—C16	1.384 (3)
C4—H4A	0.9500	C15—H15A	0.9500
C5—C6	1.386 (3)	C16—H16A	0.9500
C5—H5A	0.9500
C17—O2—C14	117.40 (18)	C10—C9—C1	132.40 (19)
C2—C1—C9	103.78 (16)	C8—C9—C1	107.68 (17)
C2—C1—H1A	111.0	C9—C10—C11	129.92 (19)
C9—C1—H1A	111.0	C9—C10—H10A	115.0
C2—C1—H1B	111.0	C11—C10—H10A	115.0
C9—C1—H1B	111.0	C12—C11—C16	118.21 (19)
H1A—C1—H1B	109.0	C12—C11—C10	117.70 (17)
C3—C2—C7	119.75 (19)	C16—C11—C10	124.08 (19)
C3—C2—C1	128.79 (18)	C13—C12—C11	121.48 (18)
C7—C2—C1	111.46 (17)	C13—C12—H12A	119.3
C4—C3—C2	118.33 (19)	C11—C12—H12A	119.3
C4—C3—H3A	120.8	C12—C13—C14	118.15 (19)
C2—C3—H3A	120.8	C12—C13—H13A	120.9
C3—C4—C5	121.8 (2)	C14—C13—H13A	120.9
C3—C4—H4A	119.1	C15—C14—C13	122.39 (19)
C5—C4—H4A	119.1	C15—C14—O2	117.17 (18)
C6—C5—C4	120.1 (2)	C13—C14—O2	120.18 (19)
C6—C5—H5A	120.0	C14—C15—C16	118.77 (18)
C4—C5—H5A	120.0	C14—C15—H15A	120.6
C5—C6—C7	118.19 (19)	C16—C15—H15A	120.6
C5—C6—H6A	120.9	C15—C16—C11	120.89 (19)
C7—C6—H6A	120.9	C15—C16—H16A	119.6
C6—C7—C2	121.90 (18)	C11—C16—H16A	119.6
C6—C7—C8	128.58 (18)	F3—C17—F2	107.74 (19)
C2—C7—C8	109.52 (17)	F3—C17—F1	108.00 (19)
O1—C8—C7	127.16 (19)	F2—C17—F1	106.5 (2)
O1—C8—C9	125.34 (19)	F3—C17—O2	107.9 (2)
C7—C8—C9	107.49 (16)	F2—C17—O2	113.2 (2)
C10—C9—C8	119.89 (18)	F1—C17—O2	113.3 (2)
C9—C1—C2—C3	178.8 (2)	C2—C1—C9—C10	179.7 (2)
C9—C1—C2—C7	−0.3 (2)	C2—C1—C9—C8	1.8 (2)
C7—C2—C3—C4	0.4 (3)	C8—C9—C10—C11	177.73 (19)
C1—C2—C3—C4	−178.7 (2)	C1—C9—C10—C11	0.1 (4)
C2—C3—C4—C5	−0.2 (3)	C9—C10—C11—C12	179.9 (2)
C3—C4—C5—C6	−0.1 (4)	C9—C10—C11—C16	1.0 (4)
C4—C5—C6—C7	0.1 (3)	C16—C11—C12—C13	3.6 (3)
C5—C6—C7—C2	0.0 (3)	C10—C11—C12—C13	−175.43 (19)
C5—C6—C7—C8	−179.7 (2)	C11—C12—C13—C14	−2.0 (3)
C3—C2—C7—C6	−0.3 (3)	C12—C13—C14—C15	−0.7 (3)
C1—C2—C7—C6	178.95 (18)	C12—C13—C14—O2	173.25 (18)
C3—C2—C7—C8	179.50 (18)	C17—O2—C14—C15	−105.6 (2)
C1—C2—C7—C8	−1.3 (2)	C17—O2—C14—C13	80.1 (3)
C6—C7—C8—O1	1.1 (3)	C13—C14—C15—C16	1.8 (3)
C2—C7—C8—O1	−178.7 (2)	O2—C14—C15—C16	−172.35 (18)
C6—C7—C8—C9	−177.8 (2)	C14—C15—C16—C11	−0.2 (3)
C2—C7—C8—C9	2.4 (2)	C12—C11—C16—C15	−2.4 (3)
O1—C8—C9—C10	0.3 (3)	C10—C11—C16—C15	176.49 (19)
C7—C8—C9—C10	179.24 (18)	C14—O2—C17—F3	172.57 (17)
O1—C8—C9—C1	178.51 (19)	C14—O2—C17—F2	−68.3 (3)
C7—C8—C9—C1	−2.6 (2)	C14—O2—C17—F1	53.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O1i	0.99	2.51	3.304 (2)	137
C10—H10A···O1ii	0.95	2.45	3.309 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O1i	0.99	2.51	3.304 (2)	137
C10—H10A⋯O1ii	0.95	2.45	3.309 (2)	151

Symmetry codes: (i) ; (ii) .