(E)-2-(4-Bromo­benzyl­idene)indan-1-one

doi:10.1107/S1600536811031746

Acta Crystallogr Sect E Struct Rep Online. 2011 September 1; 67(Pt 9): o2306–o2307.

Published online 2011 August 11. doi: 10.1107/S1600536811031746

PMCID: PMC3200602

(E)-2-(4-Bromobenzylidene)indan-1-one

Mohamed Ashraf Ali,^a Rusli Ismail,^a Tan Soo Choon,^a Wan-Sin Loh,^b^‡ and Hoong-Kun Fun^b^*^§

^aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia

^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia

Correspondence e-mail: hkfun/at/usm.my

^‡Thomson Reuters ResearcherID: C-7581-2009.

^§Thomson Reuters ResearcherID: A-3561-2009.

Received July 29, 2011; Accepted August 5, 2011.

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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Abstract

In the title compound, C₁₆H₁₁BrO, the dihydroindene ring system is approximately planar, with a maximum deviation of 0.008 (2) Å. The mean plane of this ring system forms a dihedral angle of 3.73 (11)°, with the bromo-substituted benzene ring. In the crystal, weak intermolecular C—H (...)

O hydrogen bonds link the molecules into sheets parallel to the ab plane and further stabilization is provided by weak C—H (...)

π interactions involving the bromo-substituted benzene rings.

Related literature

For background information on indanones, see: Schumann et al. (2001

); Herzog et al. (2002

); Sato (1999

); Leoni et al. (2000

); Sugimoto (1999

); Beukes et al. (1998)

. For closely related structures, see: Ali et al. (2010

, 2011

An external file that holds a picture, illustration, etc.
Object name is e-67-o2306-scheme1.jpg Object name is e-67-o2306-scheme1.jpg

Experimental

Crystal data

C₁₆H₁₁BrO
M _r = 299.16
Monoclinic,
a = 6.1933 (7) Å
b = 4.7441 (5) Å
c = 21.8572 (19) Å
β = 99.108 (3)°
V = 634.10 (11) Å³
Z = 2
Mo Kα radiation
μ = 3.23 mm⁻¹
T = 297 K
0.35 × 0.16 × 0.06 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T _min = 0.398, T _max = 0.820
6671 measured reflections
2884 independent reflections
2314 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.027
wR(F ²) = 0.057
S = 1.00
2884 reflections
164 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.15 e Å⁻³
Absolute structure: Flack (1983 ) 1189 Friedel pairs
Flack parameter: 0.00 (6)

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

Table 1

Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811031746/lh5300sup1.cif

Click here to view.^{(17K, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031746/lh5300Isup2.hkl

Click here to view.^{(142K, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811031746/lh5300Isup3.cml

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

Acknowledgments

The authors wish to express their thanks to Universiti Sains Malaysia (USM), Penang, Malaysia, for providing research facilities. HKF and WSL thank USM for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the award of a research fellowship.

supplementary crystallographic information

Comment

Indanones and related compounds are important bioactive molecules. These compounds have been studied for various biological activities including cancer and alzheimer's type of diseases. Indanones are also used as drug intermediates, ligands of olefinic polymerisation catalysts and discotic liquid crystals (Schumann et al., 2001; Herzog et al., 2002; Sato, 1999). Another indanone analogue donepezil hydrochloride has been approved by US-FDA for the treatment of mild to moderate alzheimer's disease. This drug acts as an AChE (Acetylcholinesterase) inhibitor and some other indanones have been isolated from natural products. Being such a useful moiety, several synthetic strategies have also been developed for their synthesis (Leoni et al., 2000; Sugimoto, 1999; Beukes et al., 1998). They are very useful intermediates for the synthesis of five and six membered heterocyclic compounds. Dihydroindene derivatives exhibit diverse pharmacological activities. Chemistry of dihydroindene has been recognized as a significant field of study.

In the title compound (Fig. 1), the dihydroindene ring system (C8–C16) is approximately planar, with a maximum deviation of 0.008 (2) Å for atom C15. This ring system is almost coplanar with the benzene ring (C1–C6), with a dihedral angle of 3.73 (11)°. Bond lengths and angles are within the normal ranges and are comparable to those in the related crystal structures (Ali et al., 2010, 2011).

In the crystal (Fig. 2), intermolecular C4—H4A···O1ⁱ and C9—H9B···O1ⁱⁱ hydrogen bonds (Table 1) link the molecules into sheets parallel to the ab plane (Fig. 2) and further stabilization is provided by C—H···πⁱⁱⁱ interactions, involving the centroids of benzene rings (C10–C15; Cg1).

Experimental

A mixture of 2,3-dihydro-1H-indene-1-one (0.001 mmol) and 4-bromobenzaldehyde (0.001 mmol) was dissolved in methanol (10 mL) and to this mixture was added 30% sodium hydroxide solution (5ml). The mixture was stirred for 5 h. After completion of the reaction, as evident from TLC, the mixture was poured into crushed ice, then neutralized with concentrated HCl. The precipitated solid was filtered, washed with water and recrystallised from ethanol to yield the title compound as light yellow crystals.

Figures

Fig. 1.

The molecular structure of the title compound, showing 30% probability displacement ellipsoids.

Fig. 2.

The crystal packing of the title compound, viewed along the a axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

Crystal data

C₁₆H₁₁BrO	F(000) = 300
M_r = 299.16	D_x = 1.567 Mg m⁻³
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 2130 reflections
a = 6.1933 (7) Å	θ = 3.3–24.6°
b = 4.7441 (5) Å	µ = 3.23 mm⁻¹
c = 21.8572 (19) Å	T = 297 K
β = 99.108 (3)°	Plate, colourless
V = 634.10 (11) Å³	0.35 × 0.16 × 0.06 mm
Z = 2

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer	2884 independent reflections
Radiation source: fine-focus sealed tube	2314 reflections with I > 2σ(I)
graphite	R_int = 0.023
and ω scans	θ_max = 29.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
T_min = 0.398, T_max = 0.820	k = −6→6
6671 measured reflections	l = −29→29

Refinement

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.057	w = 1/[σ²(F_o²) + (0.0281P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
2884 reflections	Δρ_max = 0.25 e Å⁻³
164 parameters	Δρ_min = −0.15 e Å⁻³
2 restraints	Absolute structure: Flack (1983) 1189 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (6)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 (Å²)

	x	y	z	U_iso*/U_eq
Br1	1.082380 (15)	1.59421 (5)	0.528270 (11)	0.06352 (10)
O1	0.1862 (3)	0.3615 (4)	0.29957 (9)	0.0621 (5)
C1	0.5691 (4)	1.0857 (5)	0.45115 (11)	0.0475 (6)
H1A	0.4363	1.0274	0.4617	0.057*
C2	0.6967 (4)	1.2730 (6)	0.48919 (11)	0.0508 (6)
H2A	0.6505	1.3426	0.5247	0.061*
C3	0.8943 (4)	1.3551 (5)	0.47354 (11)	0.0469 (5)
C4	0.9614 (4)	1.2637 (6)	0.41993 (11)	0.0478 (6)
H4A	1.0926	1.3275	0.4093	0.057*
C5	0.8327 (4)	1.0764 (6)	0.38194 (11)	0.0466 (6)
H5A	0.8784	1.0126	0.3458	0.056*
C6	0.6340 (4)	0.9814 (6)	0.39723 (11)	0.0409 (5)
C7	0.4929 (3)	0.7746 (6)	0.36006 (10)	0.0438 (5)
H7A	0.3638	0.7333	0.3749	0.053*
C8	0.5191 (4)	0.6371 (5)	0.30879 (11)	0.0399 (5)
C9	0.7021 (4)	0.6449 (5)	0.26989 (10)	0.0414 (6)
H9A	0.7175	0.8319	0.2532	0.050*
H9B	0.8403	0.5885	0.2941	0.050*
C10	0.6285 (4)	0.4365 (5)	0.21908 (12)	0.0415 (6)
C11	0.7351 (5)	0.3606 (6)	0.17000 (12)	0.0541 (6)
H11A	0.8682	0.4418	0.1654	0.065*
C12	0.6374 (5)	0.1604 (6)	0.12821 (13)	0.0635 (7)
H12A	0.7059	0.1078	0.0951	0.076*
C13	0.4405 (6)	0.0381 (7)	0.13496 (14)	0.0609 (7)
H13A	0.3791	−0.0966	0.1065	0.073*
C14	0.3334 (4)	0.1125 (6)	0.18326 (12)	0.0529 (6)
H14A	0.2006	0.0305	0.1879	0.063*
C15	0.4308 (4)	0.3145 (5)	0.22484 (10)	0.0445 (5)
C16	0.3531 (4)	0.4282 (5)	0.28031 (12)	0.0450 (6)

Atomic displacement parameters (Å²)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.06614 (16)	0.06279 (16)	0.06060 (15)	−0.0043 (2)	0.00682 (10)	−0.00762 (18)
O1	0.0404 (9)	0.0778 (14)	0.0716 (12)	−0.0037 (9)	0.0194 (8)	−0.0069 (10)
C1	0.0478 (12)	0.0513 (15)	0.0479 (12)	0.0046 (13)	0.0210 (10)	0.0048 (12)
C2	0.0597 (15)	0.0527 (16)	0.0439 (12)	0.0045 (13)	0.0204 (11)	0.0013 (11)
C3	0.0507 (12)	0.0432 (14)	0.0467 (12)	0.0087 (11)	0.0078 (10)	0.0069 (10)
C4	0.0453 (12)	0.0522 (16)	0.0481 (12)	−0.0004 (12)	0.0138 (9)	0.0055 (12)
C5	0.0465 (12)	0.0543 (17)	0.0421 (12)	0.0031 (13)	0.0171 (9)	0.0028 (11)
C6	0.0414 (11)	0.0427 (12)	0.0402 (12)	0.0073 (11)	0.0116 (10)	0.0060 (11)
C7	0.0361 (10)	0.0533 (15)	0.0451 (12)	0.0051 (11)	0.0157 (9)	0.0090 (11)
C8	0.0346 (10)	0.0449 (14)	0.0417 (12)	0.0098 (10)	0.0109 (10)	0.0070 (10)
C9	0.0388 (12)	0.0442 (15)	0.0438 (12)	0.0063 (11)	0.0143 (10)	0.0058 (10)
C10	0.0450 (12)	0.0384 (14)	0.0425 (13)	0.0117 (11)	0.0111 (10)	0.0062 (10)
C11	0.0613 (14)	0.0538 (16)	0.0519 (13)	0.0039 (13)	0.0232 (12)	−0.0010 (12)
C12	0.083 (2)	0.0614 (18)	0.0494 (14)	0.0138 (16)	0.0208 (13)	−0.0018 (13)
C13	0.073 (2)	0.0552 (17)	0.0513 (16)	0.0106 (17)	−0.0003 (13)	−0.0036 (13)
C14	0.0481 (13)	0.0514 (16)	0.0558 (14)	0.0044 (13)	−0.0026 (11)	0.0017 (12)
C15	0.0435 (11)	0.0442 (13)	0.0455 (12)	0.0102 (11)	0.0065 (9)	0.0051 (10)
C16	0.0360 (12)	0.0512 (16)	0.0480 (13)	0.0111 (11)	0.0073 (10)	0.0076 (11)

Geometric parameters (Å, °)

Br1—C3	1.906 (3)	C8—C9	1.521 (3)
O1—C16	1.219 (3)	C9—C10	1.503 (4)
C1—C2	1.378 (4)	C9—H9A	0.9700
C1—C6	1.395 (3)	C9—H9B	0.9700
C1—H1A	0.9300	C10—C15	1.377 (4)
C2—C3	1.378 (4)	C10—C11	1.393 (4)
C2—H2A	0.9300	C11—C12	1.388 (4)
C3—C4	1.374 (3)	C11—H11A	0.9300
C4—C5	1.380 (4)	C12—C13	1.379 (5)
C4—H4A	0.9300	C12—H12A	0.9300
C5—C6	1.400 (3)	C13—C14	1.378 (4)
C5—H5A	0.9300	C13—H13A	0.9300
C6—C7	1.470 (4)	C14—C15	1.391 (4)
C7—C8	1.329 (3)	C14—H14A	0.9300
C7—H7A	0.9300	C15—C16	1.476 (3)
C8—C16	1.491 (4)

C2—C1—C6	121.6 (2)	C8—C9—H9A	111.1
C2—C1—H1A	119.2	C10—C9—H9B	111.1
C6—C1—H1A	119.2	C8—C9—H9B	111.1
C1—C2—C3	118.7 (2)	H9A—C9—H9B	109.1
C1—C2—H2A	120.7	C15—C10—C11	119.9 (2)
C3—C2—H2A	120.7	C15—C10—C9	112.3 (2)
C4—C3—C2	121.5 (2)	C11—C10—C9	127.9 (2)
C4—C3—Br1	119.07 (19)	C12—C11—C10	118.2 (3)
C2—C3—Br1	119.40 (19)	C12—C11—H11A	120.9
C3—C4—C5	119.5 (2)	C10—C11—H11A	120.9
C3—C4—H4A	120.3	C13—C12—C11	121.2 (3)
C5—C4—H4A	120.3	C13—C12—H12A	119.4
C4—C5—C6	120.6 (2)	C11—C12—H12A	119.4
C4—C5—H5A	119.7	C14—C13—C12	121.0 (3)
C6—C5—H5A	119.7	C14—C13—H13A	119.5
C1—C6—C5	118.0 (2)	C12—C13—H13A	119.5
C1—C6—C7	118.6 (2)	C13—C14—C15	117.7 (3)
C5—C6—C7	123.4 (2)	C13—C14—H14A	121.1
C8—C7—C6	130.7 (2)	C15—C14—H14A	121.1
C8—C7—H7A	114.6	C10—C15—C14	122.0 (2)
C6—C7—H7A	114.6	C10—C15—C16	109.4 (2)
C7—C8—C16	120.7 (2)	C14—C15—C16	128.7 (2)
C7—C8—C9	131.4 (2)	O1—C16—C15	126.4 (2)
C16—C8—C9	108.0 (2)	O1—C16—C8	126.5 (2)
C10—C9—C8	103.4 (2)	C15—C16—C8	107.0 (2)
C10—C9—H9A	111.1

C6—C1—C2—C3	−0.8 (4)	C9—C10—C11—C12	179.6 (3)
C1—C2—C3—C4	2.7 (4)	C10—C11—C12—C13	−0.3 (4)
C1—C2—C3—Br1	−175.86 (18)	C11—C12—C13—C14	0.5 (5)
C2—C3—C4—C5	−2.6 (4)	C12—C13—C14—C15	−0.1 (4)
Br1—C3—C4—C5	175.93 (18)	C11—C10—C15—C14	0.8 (4)
C3—C4—C5—C6	0.7 (4)	C9—C10—C15—C14	−179.1 (2)
C2—C1—C6—C5	−1.1 (4)	C11—C10—C15—C16	179.7 (2)
C2—C1—C6—C7	177.9 (2)	C9—C10—C15—C16	−0.3 (3)
C4—C5—C6—C1	1.2 (4)	C13—C14—C15—C10	−0.6 (4)
C4—C5—C6—C7	−177.8 (2)	C13—C14—C15—C16	−179.2 (3)
C1—C6—C7—C8	−177.5 (3)	C10—C15—C16—O1	−178.5 (3)
C5—C6—C7—C8	1.5 (4)	C14—C15—C16—O1	0.3 (4)
C6—C7—C8—C16	178.2 (2)	C10—C15—C16—C8	0.7 (3)
C6—C7—C8—C9	−0.6 (5)	C14—C15—C16—C8	179.5 (2)
C7—C8—C9—C10	179.5 (3)	C7—C8—C16—O1	−0.7 (4)
C16—C8—C9—C10	0.7 (2)	C9—C8—C16—O1	178.3 (3)
C8—C9—C10—C15	−0.2 (3)	C7—C8—C16—C15	−179.8 (2)
C8—C9—C10—C11	179.8 (3)	C9—C8—C16—C15	−0.9 (2)
C15—C10—C11—C12	−0.4 (4)

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O1ⁱ	0.93	2.56	3.199 (3)	126
C9—H9B···O1ⁱⁱ	0.97	2.38	3.256 (3)	149
C9—H9A···Cg1ⁱⁱⁱ	0.97	2.68	3.528 (3)	147

Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z; (iii) x, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5300).

References

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