(2E)-2-(4-Bromo-benzyl-idene)-2,3-di-hydro-1H-inden-1-one.

The title indan-1-one derivative, C(16)H(11)BrO, 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, supra-molecular layers in the ab plane are formed by C-H⋯O inter-actions, involving the bifurcated carbonyl O atom, as well as C-H⋯π inter-actions. 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 = 299.16

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.068

S = 0.99

2705 reflections

164 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.70 e Å−3

Δρmin = −0.35 e Å−3

Absolute structure: Flack (1983 ▶), 1288 Friedel pairs

Flack parameter: 0.343 (10)

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812006654/bt5818sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812006654/bt5818Isup3.cml

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

C16H11BrO	F(000) = 300
Mr = 299.16	Dx = 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

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	Rint = 0.039
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 3.4°
ω scan	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −6→6
Tmin = 0.798, Tmax = 1.000	l = −27→27
5083 measured reflections

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(Fo2) + (0.0265P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max < 0.001
2705 reflections	Δρmax = 0.70 e Å−3
164 parameters	Δρmin = −0.35 e Å−3
2 restraints	Absolute structure: Flack (1983), 1288 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.343 (10)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) .