(2E)-2-(4-Bromo­benzyl­idene)-2,3-di­hydro-1H-inden-1-one

Asiri, A.M.; Faidallah, H.M.; Al-Nemari, K.F.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812006654

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o755

doi:10.1107/S1600536812006654

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(2E)-2-(4-Bromobenzylidene)-2,3-dihydro-1H-inden-1-one

Abdullah M. Asiri,^a,^b ‡ Hassan M. Faidallah,^a Khulud F. Al-Nemari,^a,^b Seik Weng Ng ^c and Edward R. T. Tiekink ^c ^*

^aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah, Saudi Arabia, ^bThe Center of Excellence for Advanced Materials Research, King Abdulaziz University, Jeddah, PO Box 80203, Saudi Arabia, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 13 February 2012; accepted 14 February 2012; online 17 February 2012)

The title indan-1-one derivative, C₁₆H₁₁BrO, is planar, the r.m.s. deviation for all 18 non-H atoms being 0.071 Å. The configuration about the C=C bond [1.337 (5) Å] is E. In the crystal, supramolecular layers in the ab plane are formed by C—H⋯O interactions, involving the bifurcated carbonyl O atom, as well as C—H⋯π interactions. The studied crystal was an inversion twin.

Related literature

For the activity of related species for the treatment of Chagas disease, see: Vera-DiVaio et al. (2009 ).

Experimental

Crystal data

C₁₆H₁₁BrO
M_r = 299.16
Monoclinic, P n
a = 6.1359 (5) Å
b = 4.7512 (4) Å
c = 21.310 (3) Å
β = 96.195 (9)°
V = 617.61 (11) Å³
Z = 2
Mo Kα radiation
μ = 3.31 mm⁻¹
T = 100 K
0.20 × 0.10 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.798, T_max = 1.000
5083 measured reflections
2705 independent reflections
2455 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.068
S = 0.99
2705 reflections
164 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.35 e Å⁻³
Absolute structure: Flack (1983 ), 1288 Friedel pairs
Flack parameter: 0.343 (10)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1b⋯O1ⁱ	0.99	2.35	3.220 (5)	146
C15—H15⋯O1ⁱⁱ	0.95	2.54	3.171 (5)	124
C1—H1A⋯Cg1ⁱⁱⁱ	0.99	2.61	3.479 (4)	147
Symmetry codes: (i) x+1, y, z; (ii) x+1, y-1, z; (iii) x, y+1, z.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812006654/bt5818sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812006654/bt5818Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812006654/bt5818Isup3.cml

checkCIF report

Comment top

The motivation for the investigation of the title compound, 2-(4-bromobenzylidene)indan-1-one (I), is its relationship to some active compounds developed for the treatment of Chagas disease (Vera-DiVaio et al., 2009).

The molecule of (I), Fig. 1, is planar with a r.m.s. deviation for all 18 non-hydrogen atoms = 0.071 Å. The maximum deviations are found for the Br1 [-0.195 (1) Å] and C16 [-0.096 (3) Å] atoms. The configuration about the C9═C10 bond [1.337 (5) Å] is E.

In the crystal packing, C—H···O interactions involving the bifurcated carbonyl-O atom as well as C—H···π interactions link molecules into layers in the ab plane, Fig. 2 and Table 1. The layers stack along the c axis with no specific interactions between them, Fig. 2.

Related literature top

For the activity of related species for the treatment of Chagas disease, see: Vera-DiVaio et al. (2009).

Experimental top

A solution of the 4-bromobenzaldehyde (1.8 g, 0.01 mol) in ethanol (20 ml) was added to a stirred solution of 1-indanone (1.3 g, 0.01 mol) in ethanolic KOH (20%, 20 ml), and stirring was maintained at room temperature for 6 h. The reaction mixture was then poured onto water (200 ml) and set aside overnight. The precipitated solid product was collected by filtration, washed with water, dried and recrystallized from its ethanol solution as blocks; M.pt: 453–455 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the supramolecular layer in (I). The C—H···O and C—H···π interactions are shown as orange and purple dashed lines, respectively.
	Fig. 3. A view in projection down the a axis of the unit-cell contents of (I). The C—H···O and C—H···π interactions are shown as orange and purple dashed lines, respectively.

(2E)-2-(4-Bromobenzylidene)-2,3-dihydro-1H-inden-1-one top

Crystal data top

C₁₆H₁₁BrO	F(000) = 300
M_r = 299.16	D_x = 1.609 Mg m⁻³
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yac	Cell parameters from 2365 reflections
a = 6.1359 (5) Å	θ = 2.9–27.5°
b = 4.7512 (4) Å	µ = 3.31 mm⁻¹
c = 21.310 (3) Å	T = 100 K
β = 96.195 (9)°	Prism, orange
V = 617.61 (11) Å³	0.20 × 0.10 × 0.05 mm
Z = 2

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2705 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2455 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.039
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 3.4°
ω scan	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −6→6
T_min = 0.798, T_max = 1.000	l = −27→27
5083 measured reflections

Refinement top

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)] = 0.036	H-atom parameters constrained
wR(F²) = 0.068	w = 1/[σ²(F_o²) + (0.0265P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max < 0.001
2705 reflections	Δρ_max = 0.70 e Å⁻³
164 parameters	Δρ_min = −0.35 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 1288 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.343 (10)

Crystal data top

C₁₆H₁₁BrO	V = 617.61 (11) Å³
M_r = 299.16	Z = 2
Monoclinic, Pn	Mo Kα radiation
a = 6.1359 (5) Å	µ = 3.31 mm⁻¹
b = 4.7512 (4) Å	T = 100 K
c = 21.310 (3) Å	0.20 × 0.10 × 0.05 mm
β = 96.195 (9)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2705 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2455 reflections with I > 2σ(I)
T_min = 0.798, T_max = 1.000	R_int = 0.039
5083 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.068	Δρ_max = 0.70 e Å⁻³
S = 0.99	Δρ_min = −0.35 e Å⁻³
2705 reflections	Absolute structure: Flack (1983), 1288 Friedel pairs
164 parameters	Absolute structure parameter: 0.343 (10)
2 restraints

Special details top

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

	x	y	z	U_iso*/U_eq
Br1	0.50001 (3)	0.38435 (6)	0.489989 (19)	0.02212 (10)
O1	−0.1668 (4)	1.6578 (5)	0.71975 (12)	0.0216 (6)
C1	0.3820 (7)	1.3644 (7)	0.74899 (19)	0.0166 (9)
H1A	0.4144	1.1744	0.7667	0.020*
H1B	0.4993	1.4196	0.7230	0.020*
C2	0.3597 (7)	1.5761 (7)	0.80064 (19)	0.0161 (9)
C3	0.5184 (7)	1.6540 (7)	0.84972 (18)	0.0194 (8)
H3	0.6596	1.5695	0.8541	0.023*
C4	0.4630 (7)	1.8602 (7)	0.89226 (18)	0.0235 (9)
H4	0.5677	1.9145	0.9262	0.028*
C5	0.2575 (7)	1.9869 (8)	0.88561 (19)	0.0219 (9)
H5	0.2247	2.1283	0.9147	0.026*
C6	0.0998 (7)	1.9098 (8)	0.83714 (17)	0.0198 (8)
H6	−0.0412	1.9947	0.8328	0.024*
C7	0.1545 (6)	1.7034 (7)	0.79481 (17)	0.0166 (8)
C8	0.0200 (7)	1.5875 (8)	0.73932 (19)	0.0162 (9)
C9	0.1582 (6)	1.3722 (7)	0.71053 (19)	0.0137 (8)
C10	0.0759 (6)	1.2291 (7)	0.65939 (17)	0.0155 (8)
H10	−0.0727	1.2694	0.6449	0.019*
C11	0.1822 (6)	1.0181 (7)	0.62235 (17)	0.0147 (8)
C12	0.0596 (6)	0.9077 (7)	0.56840 (17)	0.0184 (8)
H12	−0.0877	0.9670	0.5581	0.022*
C13	0.1497 (6)	0.7144 (8)	0.53015 (17)	0.0197 (9)
H13	0.0652	0.6404	0.4939	0.024*
C14	0.3645 (6)	0.6305 (7)	0.54539 (17)	0.0168 (8)
C15	0.4890 (6)	0.7281 (8)	0.59864 (18)	0.0184 (8)
H15	0.6355	0.6652	0.6088	0.022*
C16	0.3964 (6)	0.9197 (7)	0.63707 (17)	0.0177 (8)
H16	0.4803	0.9856	0.6742	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02551 (18)	0.02170 (16)	0.01955 (16)	0.0011 (2)	0.00433 (13)	−0.0025 (2)
O1	0.0155 (14)	0.0269 (14)	0.0218 (14)	0.0010 (11)	−0.0003 (12)	−0.0013 (11)
C1	0.020 (2)	0.017 (2)	0.0131 (19)	0.0002 (16)	0.0018 (18)	0.0031 (15)
C2	0.022 (2)	0.0155 (18)	0.0107 (19)	−0.0047 (16)	−0.0006 (18)	0.0059 (16)
C3	0.0197 (19)	0.0189 (18)	0.0184 (19)	−0.0011 (16)	−0.0036 (16)	0.0032 (16)
C4	0.032 (2)	0.022 (2)	0.0157 (19)	−0.0059 (17)	−0.0009 (17)	0.0035 (16)
C5	0.029 (2)	0.0162 (19)	0.021 (2)	−0.0011 (17)	0.0057 (18)	0.0020 (17)
C6	0.022 (2)	0.021 (2)	0.018 (2)	−0.0028 (17)	0.0079 (16)	0.0013 (16)
C7	0.020 (2)	0.0139 (17)	0.0160 (18)	−0.0033 (15)	0.0024 (16)	0.0027 (15)
C8	0.018 (2)	0.018 (2)	0.0130 (19)	−0.0058 (17)	0.0037 (18)	0.0039 (16)
C9	0.0134 (18)	0.0120 (19)	0.016 (2)	−0.0036 (14)	0.0034 (17)	0.0046 (15)
C10	0.0146 (18)	0.0200 (19)	0.0122 (17)	−0.0016 (15)	0.0025 (15)	0.0032 (16)
C11	0.019 (2)	0.0118 (17)	0.0138 (19)	−0.0043 (15)	0.0035 (16)	0.0034 (15)
C12	0.0180 (19)	0.0155 (18)	0.0215 (19)	−0.0006 (15)	0.0010 (16)	0.0050 (16)
C13	0.020 (2)	0.0188 (19)	0.0187 (19)	−0.0022 (15)	−0.0054 (17)	0.0021 (15)
C14	0.023 (2)	0.0132 (17)	0.0157 (18)	−0.0038 (15)	0.0068 (16)	0.0025 (14)
C15	0.0158 (19)	0.0207 (18)	0.0187 (18)	0.0008 (15)	0.0022 (16)	0.0051 (16)
C16	0.020 (2)	0.0183 (19)	0.0149 (18)	−0.0040 (16)	0.0012 (15)	0.0013 (16)

Geometric parameters (Å, º) top

Br1—C14	1.914 (4)	C7—C8	1.474 (5)
O1—C8	1.223 (5)	C8—C9	1.501 (5)
C1—C2	1.508 (5)	C9—C10	1.337 (5)
C1—C9	1.522 (5)	C10—C11	1.471 (5)
C1—H1A	0.9900	C10—H10	0.9500
C1—H1B	0.9900	C11—C16	1.398 (5)
C2—C7	1.390 (5)	C11—C12	1.406 (5)
C2—C3	1.400 (5)	C12—C13	1.382 (5)
C3—C4	1.401 (5)	C12—H12	0.9500
C3—H3	0.9500	C13—C14	1.382 (5)
C4—C5	1.391 (6)	C13—H13	0.9500
C4—H4	0.9500	C14—C15	1.378 (5)
C5—C6	1.386 (5)	C15—C16	1.387 (5)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.398 (5)	C16—H16	0.9500
C6—H6	0.9500

C2—C1—C9	103.2 (3)	C7—C8—C9	106.9 (3)
C2—C1—H1A	111.1	C10—C9—C8	119.9 (4)
C9—C1—H1A	111.1	C10—C9—C1	131.8 (4)
C2—C1—H1B	111.1	C8—C9—C1	108.3 (3)
C9—C1—H1B	111.1	C9—C10—C11	129.3 (3)
H1A—C1—H1B	109.1	C9—C10—H10	115.3
C7—C2—C3	120.1 (4)	C11—C10—H10	115.3
C7—C2—C1	112.2 (3)	C16—C11—C12	117.8 (3)
C3—C2—C1	127.7 (4)	C16—C11—C10	124.6 (3)
C2—C3—C4	118.1 (4)	C12—C11—C10	117.6 (3)
C2—C3—H3	121.0	C13—C12—C11	121.2 (4)
C4—C3—H3	121.0	C13—C12—H12	119.4
C5—C4—C3	121.2 (4)	C11—C12—H12	119.4
C5—C4—H4	119.4	C14—C13—C12	119.0 (3)
C3—C4—H4	119.4	C14—C13—H13	120.5
C6—C5—C4	120.9 (4)	C12—C13—H13	120.5
C6—C5—H5	119.5	C15—C14—C13	121.8 (3)
C4—C5—H5	119.5	C15—C14—Br1	118.3 (3)
C5—C6—C7	118.0 (4)	C13—C14—Br1	119.9 (3)
C5—C6—H6	121.0	C14—C15—C16	118.8 (3)
C7—C6—H6	121.0	C14—C15—H15	120.6
C2—C7—C6	121.7 (3)	C16—C15—H15	120.6
C2—C7—C8	109.4 (3)	C15—C16—C11	121.5 (3)
C6—C7—C8	128.8 (4)	C15—C16—H16	119.3
O1—C8—C7	126.5 (4)	C11—C16—H16	119.3
O1—C8—C9	126.6 (4)

C9—C1—C2—C7	−1.2 (4)	O1—C8—C9—C1	177.3 (4)
C9—C1—C2—C3	−179.9 (4)	C7—C8—C9—C1	−1.2 (4)
C7—C2—C3—C4	0.4 (5)	C2—C1—C9—C10	−178.9 (4)
C1—C2—C3—C4	179.0 (4)	C2—C1—C9—C8	1.5 (4)
C2—C3—C4—C5	−0.8 (5)	C8—C9—C10—C11	177.7 (4)
C3—C4—C5—C6	1.0 (6)	C1—C9—C10—C11	−1.9 (7)
C4—C5—C6—C7	−0.7 (6)	C9—C10—C11—C16	2.8 (6)
C3—C2—C7—C6	−0.2 (6)	C9—C10—C11—C12	−177.2 (4)
C1—C2—C7—C6	−178.9 (3)	C16—C11—C12—C13	−1.8 (5)
C3—C2—C7—C8	179.3 (3)	C10—C11—C12—C13	178.2 (3)
C1—C2—C7—C8	0.5 (5)	C11—C12—C13—C14	−0.3 (5)
C5—C6—C7—C2	0.3 (5)	C12—C13—C14—C15	1.9 (5)
C5—C6—C7—C8	−179.0 (4)	C12—C13—C14—Br1	−175.5 (3)
C2—C7—C8—O1	−178.1 (4)	C13—C14—C15—C16	−1.3 (5)
C6—C7—C8—O1	1.3 (7)	Br1—C14—C15—C16	176.2 (3)
C2—C7—C8—C9	0.4 (4)	C14—C15—C16—C11	−1.0 (5)
C6—C7—C8—C9	179.9 (4)	C12—C11—C16—C15	2.5 (5)
O1—C8—C9—C10	−2.3 (6)	C10—C11—C16—C15	−177.5 (3)
C7—C8—C9—C10	179.1 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1b···O1ⁱ	0.99	2.35	3.220 (5)	146
C15—H15···O1ⁱⁱ	0.95	2.54	3.171 (5)	124
C1—H1A···Cg1ⁱⁱⁱ	0.99	2.61	3.479 (4)	147

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₁BrO
M_r	299.16
Crystal system, space group	Monoclinic, Pn
Temperature (K)	100
a, b, c (Å)	6.1359 (5), 4.7512 (4), 21.310 (3)
β (°)	96.195 (9)
V (Å³)	617.61 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.31
Crystal size (mm)	0.20 × 0.10 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.798, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5083, 2705, 2455
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.068, 0.99
No. of reflections	2705
No. of parameters	164
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.35
Absolute structure	Flack (1983), 1288 Friedel pairs
Absolute structure parameter	0.343 (10)

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1b···O1ⁱ	0.99	2.35	3.220 (5)	146
C15—H15···O1ⁱⁱ	0.95	2.54	3.171 (5)	124
C1—H1A···Cg1ⁱⁱⁱ	0.99	2.61	3.479 (4)	147

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

Footnotes

‡Additional correspondence author, e-mail: aasiri2@kau.edu.sa.

Acknowledgements

The authors are thankful to the Center of Excellence for Advanced Materials Research and the Chemistry Department of King Abdulaziz University for providing research facilities. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
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Volume 68| Part 3| March 2012| Page o755

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