(E)-2-[4-(Trifluoro-meth-yl)benzyl-idene]-2,3-dihydro-1H-inden-1-one.

In the title mol-ecule, C(17)H(11)F(3)O, the indan ring system and the trifluoro-methyl-substituted benzene ring are approximately individually planar and form a dihedral angle of 1.81 (5)° with each other. In the crystal, mol-ecules are linked by pairs of weak bifurcated (C-H)(2)⋯O hydrogen bonds to form centrosymmetric dimers, generating R(2) (1)(6) and R(2) (2)(10) ring motifs. These dimers are connected by further weak C-H⋯O hydrogen bonds into one-dimensional chains along the b axis. Weak C-H⋯π inter-actions are also present.

Related literature

For the biological activity of chalcone compounds, see: Gurubasavaraja Swamy & Agasimundin (2008 ▶); Shibata (1994 ▶); Charris et al. (2007 ▶); Sharma et al. (2009 ▶). For related structures, see: Ali et al. (2011a ▶,b ▶,c ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C17H11F3O

M = 288.26

Monoclinic,

a = 15.6546 (13) Å

b = 6.2050 (6) Å

c = 14.6546 (13) Å

β = 113.774 (2)°

V = 1302.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.40 × 0.18 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.954, T max = 0.988

10643 measured reflections

3804 independent reflections

3033 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.129

S = 1.06

3804 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.32 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) global, I. DOI: 10.1107/S1600536812003157/lh5408sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003157/lh5408Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812003157/lh5408Isup3.cml

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

C17H11F3O	F(000) = 592
Mr = 288.26	Dx = 1.470 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3626 reflections
a = 15.6546 (13) Å	θ = 2.8–30.1°
b = 6.2050 (6) Å	µ = 0.12 mm−1
c = 14.6546 (13) Å	T = 100 K
β = 113.774 (2)°	Plate, colourless
V = 1302.7 (2) Å3	0.40 × 0.18 × 0.10 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3804 independent reflections
Radiation source: fine-focus sealed tube	3033 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 30.1°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −21→22
Tmin = 0.954, Tmax = 0.988	k = −8→8
10643 measured reflections	l = −20→20

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0567P)2 + 0.6847P] where P = (Fo2 + 2Fc2)/3
3804 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.32 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	−0.41885 (6)	0.88298 (16)	0.17877 (8)	0.0335 (2)
F2	−0.47050 (6)	0.62598 (19)	0.23994 (8)	0.0392 (3)
F3	−0.45949 (7)	0.5856 (2)	0.09945 (8)	0.0450 (3)
O1	0.11757 (7)	0.05902 (17)	0.48959 (8)	0.0225 (2)
C1	0.07259 (8)	0.5913 (2)	0.37708 (10)	0.0170 (3)
H1A	0.0478	0.6137	0.3041	0.020*
H1B	0.0544	0.7149	0.4081	0.020*
C2	0.17752 (8)	0.5624 (2)	0.42083 (9)	0.0158 (2)
C3	0.24539 (9)	0.7074 (2)	0.42066 (10)	0.0192 (3)
H3A	0.2285	0.8445	0.3897	0.023*
C4	0.33894 (9)	0.6456 (3)	0.46729 (10)	0.0221 (3)
H4A	0.3861	0.7427	0.4680	0.026*
C5	0.36474 (9)	0.4440 (3)	0.51297 (10)	0.0215 (3)
H5A	0.4289	0.4062	0.5440	0.026*
C6	0.29734 (9)	0.2987 (2)	0.51332 (9)	0.0187 (3)
H6A	0.3141	0.1614	0.5441	0.022*
C7	0.20371 (8)	0.3623 (2)	0.46647 (9)	0.0154 (2)
C8	0.12026 (8)	0.2400 (2)	0.45815 (9)	0.0166 (3)
C9	0.03802 (8)	0.3802 (2)	0.40223 (9)	0.0163 (2)
C10	−0.04785 (8)	0.3083 (2)	0.38672 (9)	0.0167 (2)
H10A	−0.0496	0.1677	0.4116	0.020*
C11	−0.13924 (8)	0.4128 (2)	0.33745 (9)	0.0164 (2)
C12	−0.21766 (8)	0.2952 (2)	0.33344 (9)	0.0159 (2)
H12A	−0.2091	0.1570	0.3637	0.019*
C13	−0.30716 (8)	0.3780 (2)	0.28612 (9)	0.0173 (3)
H13A	−0.3595	0.2959	0.2829	0.021*
C14	−0.31963 (8)	0.5819 (2)	0.24335 (9)	0.0166 (3)
C15	−0.24327 (9)	0.7038 (2)	0.24696 (9)	0.0175 (3)
H15A	−0.2523	0.8430	0.2176	0.021*
C16	−0.15373 (9)	0.6189 (2)	0.29410 (10)	0.0182 (3)
H16A	−0.1016	0.7016	0.2970	0.022*
C17	−0.41652 (9)	0.6688 (3)	0.19105 (10)	0.0219 (3)

	U11	U22	U33	U12	U13	U23
F1	0.0274 (4)	0.0258 (5)	0.0519 (6)	0.0129 (4)	0.0208 (4)	0.0134 (5)
F2	0.0209 (4)	0.0532 (7)	0.0507 (6)	0.0122 (4)	0.0218 (4)	0.0260 (5)
F3	0.0284 (5)	0.0563 (8)	0.0316 (5)	0.0171 (5)	−0.0074 (4)	−0.0106 (5)
O1	0.0210 (4)	0.0179 (5)	0.0275 (5)	−0.0019 (4)	0.0086 (4)	0.0045 (4)
C1	0.0148 (5)	0.0169 (6)	0.0181 (5)	−0.0023 (5)	0.0055 (4)	0.0026 (5)
C2	0.0156 (5)	0.0179 (6)	0.0143 (5)	−0.0030 (5)	0.0065 (4)	−0.0011 (5)
C3	0.0192 (6)	0.0195 (7)	0.0196 (6)	−0.0044 (5)	0.0086 (5)	−0.0004 (5)
C4	0.0177 (6)	0.0274 (8)	0.0227 (6)	−0.0077 (5)	0.0097 (5)	−0.0034 (6)
C5	0.0143 (5)	0.0296 (8)	0.0197 (6)	−0.0025 (5)	0.0061 (5)	−0.0029 (6)
C6	0.0161 (5)	0.0218 (7)	0.0175 (5)	−0.0004 (5)	0.0059 (4)	−0.0018 (5)
C7	0.0140 (5)	0.0178 (6)	0.0145 (5)	−0.0026 (5)	0.0059 (4)	−0.0015 (5)
C8	0.0145 (5)	0.0179 (6)	0.0162 (5)	−0.0016 (5)	0.0050 (4)	−0.0003 (5)
C9	0.0162 (5)	0.0154 (6)	0.0165 (5)	−0.0003 (5)	0.0059 (4)	−0.0002 (5)
C10	0.0159 (5)	0.0157 (6)	0.0176 (5)	0.0001 (5)	0.0059 (4)	−0.0002 (5)
C11	0.0141 (5)	0.0178 (6)	0.0155 (5)	−0.0006 (5)	0.0042 (4)	0.0008 (5)
C12	0.0146 (5)	0.0157 (6)	0.0164 (5)	−0.0010 (5)	0.0053 (4)	0.0008 (5)
C13	0.0141 (5)	0.0194 (6)	0.0186 (6)	−0.0013 (5)	0.0069 (4)	0.0002 (5)
C14	0.0149 (5)	0.0191 (6)	0.0161 (5)	0.0032 (5)	0.0065 (4)	0.0002 (5)
C15	0.0185 (6)	0.0163 (6)	0.0176 (5)	0.0019 (5)	0.0071 (4)	0.0021 (5)
C16	0.0163 (5)	0.0180 (6)	0.0190 (6)	−0.0020 (5)	0.0057 (4)	0.0023 (5)
C17	0.0174 (6)	0.0252 (7)	0.0236 (6)	0.0059 (5)	0.0088 (5)	0.0054 (6)

F1—C17	1.3395 (18)	C6—H6A	0.9500
F2—C17	1.3365 (16)	C7—C8	1.4727 (17)
F3—C17	1.3391 (18)	C8—C9	1.4951 (18)
O1—C8	1.2211 (17)	C9—C10	1.3460 (17)
C1—C2	1.5141 (17)	C10—C11	1.4683 (17)
C1—C9	1.5180 (19)	C10—H10A	0.9500
C1—H1A	0.9900	C11—C16	1.4049 (19)
C1—H1B	0.9900	C11—C12	1.4090 (17)
C2—C7	1.3912 (19)	C12—C13	1.3871 (17)
C2—C3	1.3932 (18)	C12—H12A	0.9500
C3—C4	1.3971 (19)	C13—C14	1.3907 (19)
C3—H3A	0.9500	C13—H13A	0.9500
C4—C5	1.399 (2)	C14—C15	1.3974 (18)
C4—H4A	0.9500	C14—C17	1.4972 (17)
C5—C6	1.3895 (19)	C15—C16	1.3926 (18)
C5—H5A	0.9500	C15—H15A	0.9500
C6—C7	1.4016 (17)	C16—H16A	0.9500
C2—C1—C9	103.13 (11)	C8—C9—C1	108.82 (10)
C2—C1—H1A	111.1	C9—C10—C11	130.19 (13)
C9—C1—H1A	111.1	C9—C10—H10A	114.9
C2—C1—H1B	111.1	C11—C10—H10A	114.9
C9—C1—H1B	111.1	C16—C11—C12	118.25 (11)
H1A—C1—H1B	109.1	C16—C11—C10	124.90 (11)
C7—C2—C3	120.00 (12)	C12—C11—C10	116.85 (12)
C7—C2—C1	111.62 (11)	C13—C12—C11	121.11 (12)
C3—C2—C1	128.37 (12)	C13—C12—H12A	119.4
C2—C3—C4	118.14 (13)	C11—C12—H12A	119.4
C2—C3—H3A	120.9	C12—C13—C14	119.48 (12)
C4—C3—H3A	120.9	C12—C13—H13A	120.3
C3—C4—C5	121.53 (13)	C14—C13—H13A	120.3
C3—C4—H4A	119.2	C13—C14—C15	120.86 (12)
C5—C4—H4A	119.2	C13—C14—C17	119.19 (12)
C6—C5—C4	120.58 (12)	C15—C14—C17	119.94 (12)
C6—C5—H5A	119.7	C16—C15—C14	119.25 (13)
C4—C5—H5A	119.7	C16—C15—H15A	120.4
C5—C6—C7	117.46 (13)	C14—C15—H15A	120.4
C5—C6—H6A	121.3	C15—C16—C11	121.03 (12)
C7—C6—H6A	121.3	C15—C16—H16A	119.5
C2—C7—C6	122.29 (12)	C11—C16—H16A	119.5
C2—C7—C8	109.90 (11)	F2—C17—F3	106.87 (13)
C6—C7—C8	127.81 (13)	F2—C17—F1	106.30 (12)
O1—C8—C7	127.37 (12)	F3—C17—F1	105.80 (12)
O1—C8—C9	126.09 (12)	F2—C17—C14	112.52 (11)
C7—C8—C9	106.53 (11)	F3—C17—C14	111.72 (12)
C10—C9—C8	118.70 (12)	F1—C17—C14	113.15 (12)
C10—C9—C1	132.43 (12)
C9—C1—C2—C7	−0.08 (14)	C2—C1—C9—C8	0.30 (13)
C9—C1—C2—C3	−179.37 (13)	C8—C9—C10—C11	178.11 (12)
C7—C2—C3—C4	−0.10 (19)	C1—C9—C10—C11	1.1 (2)
C1—C2—C3—C4	179.14 (13)	C9—C10—C11—C16	0.8 (2)
C2—C3—C4—C5	0.2 (2)	C9—C10—C11—C12	−179.53 (13)
C3—C4—C5—C6	−0.1 (2)	C16—C11—C12—C13	1.41 (19)
C4—C5—C6—C7	0.02 (19)	C10—C11—C12—C13	−178.26 (12)
C3—C2—C7—C6	0.01 (19)	C11—C12—C13—C14	−1.11 (19)
C1—C2—C7—C6	−179.36 (12)	C12—C13—C14—C15	0.38 (19)
C3—C2—C7—C8	179.18 (11)	C12—C13—C14—C17	179.09 (12)
C1—C2—C7—C8	−0.18 (15)	C13—C14—C15—C16	0.01 (19)
C5—C6—C7—C2	0.03 (19)	C17—C14—C15—C16	−178.69 (12)
C5—C6—C7—C8	−178.99 (12)	C14—C15—C16—C11	0.3 (2)
C2—C7—C8—O1	179.80 (13)	C12—C11—C16—C15	−1.01 (19)
C6—C7—C8—O1	−1.1 (2)	C10—C11—C16—C15	178.63 (12)
C2—C7—C8—C9	0.36 (14)	C13—C14—C17—F2	41.38 (18)
C6—C7—C8—C9	179.48 (12)	C15—C14—C17—F2	−139.90 (14)
O1—C8—C9—C10	2.5 (2)	C13—C14—C17—F3	−78.84 (16)
C7—C8—C9—C10	−178.09 (11)	C15—C14—C17—F3	99.88 (16)
O1—C8—C9—C1	−179.86 (13)	C13—C14—C17—F1	161.88 (12)
C7—C8—C9—C1	−0.41 (14)	C15—C14—C17—F1	−19.40 (18)
C2—C1—C9—C10	177.55 (14)

Cg1 and Cg2 are the centroids of the C2–C7 and C11–C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O1i	0.99	2.45	3.2713 (17)	140.
C10—H10A···O1ii	0.95	2.54	3.3566 (17)	144.
C12—H12A···O1ii	0.95	2.45	3.2765 (17)	146.
C15—H15A···Cg1iii	0.95	2.78	3.5163 (14)	135.
C3—H3A···Cg2iii	0.95	2.81	3.5035 (15)	130.

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C11–C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O1i	0.99	2.45	3.2713 (17)	140
C10—H10A⋯O1ii	0.95	2.54	3.3566 (17)	144
C12—H12A⋯O1ii	0.95	2.45	3.2765 (17)	146
C15—H15A⋯Cg1iii	0.95	2.78	3.5163 (14)	135
C3—H3A⋯Cg2iii	0.95	2.81	3.5035 (15)	130

Symmetry codes: (i) ; (ii) ; (iii) .