2-Bromo-1-(4-methyl-phen-yl)-3-phenyl-prop-2-en-1-one.

In the crystal structure of the title compound, C(16)H(13)BrO, the two benzene rings are twisted from each other with a dihedral angle of 52.55 (9)°. Both an intra-molecular C-H⋯Br hydrogen bond, which generates an S(6) ring motif, and a short Br⋯O contact [2.9907 (19) Å] may influence the conformation of the mol-ecule. The crystal packing is stabilized by weak inter-molecular C-H⋯O inter-actions.

Related literature

For related literature on chalcone derivatives, see: Fun et al. (2008 ▶); Patil et al. (2006 ▶, 2007 ▶). For related literature on experimental preparation, see: Shivarama Holla et al. (2006 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H13BrO

M = 301.17

Orthorhombic,

a = 8.7192 (2) Å

b = 11.5819 (2) Å

c = 26.4769 (6) Å

V = 2673.77 (10) Å3

Z = 8

Mo Kα radiation

μ = 3.06 mm−1

T = 100.0 (1) K

0.20 × 0.20 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.556, T max = 0.715

14370 measured reflections

3893 independent reflections

2462 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.090

S = 1.00

3893 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.54 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022289/lh2662sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022289/lh2662Isup2.hkl

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

C16H13BrO	F000 = 1216
Mr = 301.17	Dx = 1.496 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1664 reflections
a = 8.7192 (2) Å	θ = 2.8–23.7º
b = 11.5819 (2) Å	µ = 3.06 mm−1
c = 26.4769 (6) Å	T = 100.0 (1) K
V = 2673.77 (10) Å3	Block, colourless
Z = 8	0.20 × 0.20 × 0.11 mm

Bruker SMART APEXII CCD area-detector diffractometer	3893 independent reflections
Radiation source: fine-focus sealed tube	2462 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.070
T = 100.0(1) K	θmax = 30.1º
φ and ω scans	θmin = 2.8º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −12→9
Tmin = 0.556, Tmax = 0.715	k = −16→12
14370 measured reflections	l = −36→16

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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0317P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
3893 reflections	Δρmax = 0.43 e Å−3
164 parameters	Δρmin = −0.54 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Br1	0.13862 (3)	0.42397 (2)	0.062535 (10)	0.02216 (9)
O1	0.3082 (2)	0.38663 (17)	0.15935 (7)	0.0253 (5)
C1	0.4236 (3)	0.6775 (2)	0.16809 (10)	0.0177 (6)
H1A	0.3563	0.7084	0.1444	0.021*
C2	0.4991 (4)	0.7501 (3)	0.20151 (10)	0.0228 (7)
H2A	0.4813	0.8292	0.2005	0.027*
C3	0.6008 (4)	0.7049 (3)	0.23638 (10)	0.0262 (7)
H3A	0.6512	0.7537	0.2588	0.031*
C4	0.6275 (4)	0.5867 (3)	0.23785 (10)	0.0266 (7)
H4A	0.6977	0.5565	0.2608	0.032*
C5	0.5499 (3)	0.5141 (3)	0.20533 (10)	0.0214 (6)
H5A	0.5657	0.4348	0.2071	0.026*
C6	0.4477 (3)	0.5591 (2)	0.16967 (9)	0.0158 (6)
C7	0.3529 (3)	0.4759 (2)	0.13968 (9)	0.0159 (6)
C8	0.3122 (3)	0.5048 (2)	0.08629 (9)	0.0144 (6)
C9	0.3995 (3)	0.5748 (2)	0.05796 (9)	0.0143 (5)
H9A	0.4848	0.6018	0.0754	0.017*
C10	0.3931 (3)	0.6191 (2)	0.00603 (9)	0.0150 (6)
C11	0.2836 (3)	0.5907 (2)	−0.03059 (10)	0.0188 (6)
H11A	0.2098	0.5348	−0.0238	0.023*
C12	0.2854 (3)	0.6461 (3)	−0.07730 (10)	0.0214 (6)
H12A	0.2119	0.6268	−0.1013	0.026*
C13	0.3942 (3)	0.7295 (2)	−0.08878 (9)	0.0198 (6)
C14	0.5065 (4)	0.7535 (2)	−0.05306 (9)	0.0208 (6)
H14A	0.5829	0.8070	−0.0605	0.025*
C15	0.5059 (3)	0.6990 (2)	−0.00666 (9)	0.0176 (6)
H15A	0.5825	0.7160	0.0166	0.021*
C16	0.3901 (4)	0.7951 (3)	−0.13811 (10)	0.0304 (8)
H16A	0.3307	0.7526	−0.1624	0.046*
H16B	0.4928	0.8047	−0.1506	0.046*
H16C	0.3444	0.8694	−0.1328	0.046*

	U11	U22	U33	U12	U13	U23
Br1	0.02062 (15)	0.02191 (16)	0.02395 (15)	−0.00743 (14)	−0.00516 (12)	0.00364 (12)
O1	0.0315 (13)	0.0193 (11)	0.0252 (11)	−0.0079 (10)	−0.0037 (9)	0.0057 (9)
C1	0.0193 (15)	0.0186 (15)	0.0152 (13)	0.0013 (13)	0.0009 (11)	0.0003 (11)
C2	0.0271 (17)	0.0233 (16)	0.0180 (13)	−0.0026 (14)	0.0031 (12)	−0.0054 (12)
C3	0.0308 (19)	0.0347 (19)	0.0130 (13)	−0.0064 (16)	−0.0013 (12)	−0.0074 (12)
C4	0.0237 (16)	0.039 (2)	0.0169 (13)	−0.0012 (17)	−0.0041 (12)	0.0032 (12)
C5	0.0280 (17)	0.0193 (16)	0.0170 (13)	0.0043 (14)	0.0008 (13)	0.0025 (11)
C6	0.0167 (14)	0.0197 (16)	0.0110 (12)	0.0007 (12)	0.0033 (10)	0.0019 (10)
C7	0.0152 (14)	0.0149 (14)	0.0177 (13)	0.0020 (12)	0.0008 (11)	0.0013 (11)
C8	0.0141 (13)	0.0136 (14)	0.0155 (13)	−0.0018 (11)	−0.0013 (11)	−0.0022 (10)
C9	0.0121 (13)	0.0138 (13)	0.0168 (12)	0.0022 (12)	−0.0004 (10)	−0.0039 (11)
C10	0.0198 (16)	0.0109 (13)	0.0142 (12)	0.0038 (12)	−0.0001 (11)	−0.0029 (10)
C11	0.0184 (15)	0.0199 (16)	0.0181 (13)	0.0010 (13)	0.0005 (11)	−0.0011 (11)
C12	0.0199 (16)	0.0273 (17)	0.0171 (13)	0.0038 (14)	−0.0025 (11)	−0.0013 (12)
C13	0.0250 (17)	0.0218 (15)	0.0125 (13)	0.0074 (13)	0.0041 (11)	0.0027 (11)
C14	0.0274 (17)	0.0174 (15)	0.0177 (13)	−0.0021 (13)	0.0047 (12)	0.0022 (11)
C15	0.0214 (15)	0.0157 (15)	0.0157 (13)	−0.0024 (13)	−0.0004 (11)	−0.0033 (11)
C16	0.036 (2)	0.0352 (19)	0.0198 (14)	0.0072 (16)	−0.0008 (13)	0.0096 (13)

Br1—C8	1.888 (3)	C9—C10	1.469 (3)
O1—C7	1.221 (3)	C9—H9A	0.9300
C1—C2	1.386 (4)	C10—C15	1.391 (4)
C1—C6	1.388 (4)	C10—C11	1.400 (4)
C1—H1A	0.9300	C11—C12	1.394 (4)
C2—C3	1.383 (4)	C11—H11A	0.9300
C2—H2A	0.9300	C12—C13	1.387 (4)
C3—C4	1.390 (4)	C12—H12A	0.9300
C3—H3A	0.9300	C13—C14	1.389 (4)
C4—C5	1.381 (4)	C13—C16	1.511 (4)
C4—H4A	0.9300	C14—C15	1.382 (3)
C5—C6	1.399 (4)	C14—H14A	0.9300
C5—H5A	0.9300	C15—H15A	0.9300
C6—C7	1.497 (4)	C16—H16A	0.9600
C7—C8	1.496 (3)	C16—H16B	0.9600
C8—C9	1.341 (4)	C16—H16C	0.9600
C2—C1—C6	120.5 (3)	C10—C9—H9A	112.3
C2—C1—H1A	119.7	C15—C10—C11	118.1 (2)
C6—C1—H1A	119.7	C15—C10—C9	115.5 (2)
C3—C2—C1	120.1 (3)	C11—C10—C9	126.3 (3)
C3—C2—H2A	120.0	C12—C11—C10	119.9 (3)
C1—C2—H2A	120.0	C12—C11—H11A	120.1
C2—C3—C4	119.9 (3)	C10—C11—H11A	120.1
C2—C3—H3A	120.0	C13—C12—C11	121.5 (3)
C4—C3—H3A	120.0	C13—C12—H12A	119.2
C5—C4—C3	120.0 (3)	C11—C12—H12A	119.2
C5—C4—H4A	120.0	C12—C13—C14	118.2 (2)
C3—C4—H4A	120.0	C12—C13—C16	121.5 (3)
C4—C5—C6	120.4 (3)	C14—C13—C16	120.3 (3)
C4—C5—H5A	119.8	C15—C14—C13	120.7 (3)
C6—C5—H5A	119.8	C15—C14—H14A	119.6
C1—C6—C5	119.0 (3)	C13—C14—H14A	119.6
C1—C6—C7	122.4 (2)	C14—C15—C10	121.4 (3)
C5—C6—C7	118.0 (2)	C14—C15—H15A	119.3
O1—C7—C8	121.1 (2)	C10—C15—H15A	119.3
O1—C7—C6	119.7 (2)	C13—C16—H16A	109.5
C8—C7—C6	119.2 (2)	C13—C16—H16B	109.5
C9—C8—C7	122.0 (2)	H16A—C16—H16B	109.5
C9—C8—Br1	124.7 (2)	C13—C16—H16C	109.5
C7—C8—Br1	113.19 (19)	H16A—C16—H16C	109.5
C8—C9—C10	135.5 (3)	H16B—C16—H16C	109.5
C8—C9—H9A	112.3
C6—C1—C2—C3	0.8 (4)	C6—C7—C8—Br1	−158.5 (2)
C1—C2—C3—C4	0.1 (4)	C7—C8—C9—C10	179.8 (3)
C2—C3—C4—C5	−1.5 (4)	Br1—C8—C9—C10	5.1 (5)
C3—C4—C5—C6	2.0 (4)	C8—C9—C10—C15	175.3 (3)
C2—C1—C6—C5	−0.3 (4)	C8—C9—C10—C11	−3.2 (5)
C2—C1—C6—C7	171.0 (3)	C15—C10—C11—C12	−3.1 (4)
C4—C5—C6—C1	−1.1 (4)	C9—C10—C11—C12	175.3 (3)
C4—C5—C6—C7	−172.8 (3)	C10—C11—C12—C13	0.3 (4)
C1—C6—C7—O1	−136.9 (3)	C11—C12—C13—C14	2.5 (4)
C5—C6—C7—O1	34.5 (4)	C11—C12—C13—C16	−176.0 (3)
C1—C6—C7—C8	42.0 (4)	C12—C13—C14—C15	−2.4 (4)
C5—C6—C7—C8	−146.6 (3)	C16—C13—C14—C15	176.1 (3)
O1—C7—C8—C9	−154.8 (3)	C13—C14—C15—C10	−0.5 (4)
C6—C7—C8—C9	26.3 (4)	C11—C10—C15—C14	3.2 (4)
O1—C7—C8—Br1	20.4 (3)	C9—C10—C15—C14	−175.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1i	0.93	2.54	3.163 (3)	124
C11—H11A···Br1	0.93	2.69	3.377 (3)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O1i	0.93	2.54	3.163 (3)	124
C11—H11A⋯Br1	0.93	2.69	3.377 (3)	131

Symmetry code: (i) .