(E)-1-(4-Bromo-phen-yl)-3-(2-chloro-phen-yl)prop-2-en-1-one.

The structure of the title compound, C(15)H(10)BrClO, comprises two substituted benzene rings bridged by a prop-2-en-1-one group and exists in an E configuration about the C=N double bond. The dihedral angle formed between the 4-bromo-phenyl and 2-chloro-phenyl rings is 23.77 (18)°. In the crystal structure, the mol-ecules are linked by weak C-H⋯O inter-actions, forming a supra-molecular zigzag chain. Intramolecular C-H⋯Cl and C-H⋯O hydrogen bonds are also present.

Related literature

For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Patil et al. (2007 ▶); Moorthi et al. (2005 ▶). For applications of chalcones, see: Gu et al. (2008 ▶); Mishra et al. (2008 ▶); Nel et al. (1998 ▶); Patil & Dharmaprakash (2008 ▶); Wang et al. (2004 ▶).

Experimental

Crystal data

C15H10BrClO

M = 321.59

Orthorhombic,

a = 27.8720 (6) Å

b = 3.9235 (1) Å

c = 11.6408 (2) Å

V = 1272.99 (5) Å3

Z = 4

Mo Kα radiation

μ = 3.42 mm−1

T = 100.0 (1) K

0.33 × 0.18 × 0.09 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.392, T max = 0.736

9658 measured reflections

3495 independent reflections

2938 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.086

S = 1.03

3495 reflections

163 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.44 e Å−3

Absolute structure: Flack (1983 ▶), 1545 Friedel pairs

Flack parameter: 0.011 (12)

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/S1600536808020795/tk2281sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020795/tk2281Isup2.hkl

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

C15H10BrClO	F000 = 640
Mr = 321.59	Dx = 1.678 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3495 reflections
a = 27.8720 (6) Å	θ = 1.5–30.0º
b = 3.9235 (1) Å	µ = 3.42 mm−1
c = 11.6408 (2) Å	T = 100.0 (1) K
V = 1272.99 (5) Å3	Block, colorless
Z = 4	0.33 × 0.18 × 0.09 mm

Bruker SMART APEX2 CCD area-detector diffractometer	3495 independent reflections
Radiation source: fine-focus sealed tube	2938 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.044
Detector resolution: 8.33 pixels mm-1	θmax = 30.0º
T = 100.0(1) K	θmin = 1.5º
ω scans	h = −36→39
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −5→3
Tmin = 0.392, Tmax = 0.736	l = −16→16
9658 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.033	w = 1/[σ2(Fo2) + 1.3265P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.086	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.41 e Å−3
3495 reflections	Δρmin = −0.44 e Å−3
163 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 1545 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.011 (12)
Secondary atom site location: difference Fourier map

Experimental. The low-temperature 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	0.165695 (11)	0.71499 (8)	0.27469 (5)	0.02346 (10)
Cl1	−0.18444 (4)	−0.5643 (3)	0.47411 (9)	0.0264 (2)
O1	−0.03953 (10)	0.0955 (8)	0.5096 (2)	0.0254 (6)
C1	0.03194 (13)	0.2560 (9)	0.2561 (3)	0.0187 (8)
H1A	0.0132	0.1502	0.2004	0.022*
C2	0.07645 (13)	0.3879 (11)	0.2266 (3)	0.0192 (8)
H2A	0.0878	0.3720	0.1517	0.023*
C3	0.10349 (14)	0.5426 (9)	0.3106 (3)	0.0192 (8)
C4	0.08725 (13)	0.5741 (10)	0.4230 (3)	0.0202 (8)
H4A	0.1059	0.6831	0.4782	0.024*
C5	0.04319 (13)	0.4411 (9)	0.4510 (3)	0.0177 (8)
H5A	0.0321	0.4585	0.5261	0.021*
C6	0.01502 (13)	0.2810 (9)	0.3686 (3)	0.0156 (7)
C7	−0.03108 (13)	0.1245 (10)	0.4073 (3)	0.0180 (8)
C8	−0.06613 (13)	0.0089 (10)	0.3202 (3)	0.0185 (8)
H8A	−0.0610	0.0543	0.2428	0.022*
C9	−0.10501 (14)	−0.1603 (10)	0.3534 (3)	0.0192 (8)
H9A	−0.1074	−0.2079	0.4315	0.023*
C10	−0.14477 (11)	−0.2809 (8)	0.2809 (5)	0.0180 (6)
C11	−0.18352 (14)	−0.4627 (10)	0.3288 (3)	0.0206 (8)
C12	−0.22195 (13)	−0.5699 (9)	0.2625 (4)	0.0246 (8)
H12A	−0.2470	−0.6907	0.2960	0.030*
C13	−0.22293 (15)	−0.4970 (11)	0.1464 (4)	0.0276 (9)
H13A	−0.2488	−0.5662	0.1017	0.033*
C14	−0.18509 (15)	−0.3199 (11)	0.0968 (3)	0.0239 (8)
H14A	−0.1856	−0.2719	0.0185	0.029*
C15	−0.14652 (15)	−0.2140 (10)	0.1632 (3)	0.0213 (8)
H15A	−0.1214	−0.0963	0.1287	0.026*

	U11	U22	U33	U12	U13	U23
Br1	0.01631 (16)	0.02108 (18)	0.03298 (17)	−0.00286 (13)	0.0010 (2)	0.0002 (3)
Cl1	0.0257 (5)	0.0253 (5)	0.0282 (4)	−0.0021 (4)	0.0095 (4)	0.0033 (4)
O1	0.0260 (16)	0.0329 (18)	0.0171 (13)	−0.0047 (13)	0.0038 (11)	0.0008 (11)
C1	0.0159 (16)	0.0214 (19)	0.019 (2)	−0.0002 (13)	−0.0025 (13)	0.0006 (14)
C2	0.0177 (19)	0.021 (2)	0.0187 (16)	−0.0023 (15)	−0.0003 (14)	0.0018 (15)
C3	0.0170 (18)	0.0126 (19)	0.0278 (19)	0.0004 (14)	−0.0001 (14)	0.0023 (14)
C4	0.0186 (19)	0.017 (2)	0.0248 (19)	0.0025 (15)	−0.0068 (15)	−0.0046 (15)
C5	0.0180 (18)	0.017 (2)	0.0180 (17)	0.0023 (14)	0.0011 (13)	−0.0021 (14)
C6	0.0138 (17)	0.0161 (19)	0.0169 (16)	0.0025 (14)	−0.0010 (13)	0.0003 (13)
C7	0.0176 (18)	0.015 (2)	0.0218 (17)	0.0042 (14)	−0.0011 (14)	0.0011 (14)
C8	0.0153 (18)	0.022 (2)	0.0178 (16)	−0.0010 (15)	0.0015 (14)	0.0020 (14)
C9	0.018 (2)	0.020 (2)	0.0195 (16)	0.0021 (15)	−0.0003 (14)	0.0000 (14)
C10	0.0150 (14)	0.0143 (15)	0.0248 (15)	0.0030 (12)	0.001 (2)	0.0027 (19)
C11	0.0184 (19)	0.015 (2)	0.0280 (19)	0.0060 (15)	0.0042 (15)	0.0010 (15)
C12	0.0177 (17)	0.0158 (18)	0.040 (2)	0.0019 (13)	0.0016 (18)	−0.004 (2)
C13	0.020 (2)	0.022 (2)	0.041 (2)	0.0077 (17)	−0.0090 (18)	−0.0105 (18)
C14	0.025 (2)	0.025 (2)	0.0220 (19)	0.0065 (17)	−0.0067 (16)	−0.0013 (16)
C15	0.021 (2)	0.017 (2)	0.0257 (19)	−0.0003 (15)	0.0010 (15)	0.0019 (15)

Br1—C3	1.907 (4)	C8—C9	1.328 (5)
Cl1—C11	1.738 (4)	C8—H8A	0.9300
O1—C7	1.219 (4)	C9—C10	1.472 (6)
C1—C2	1.387 (5)	C9—H9A	0.9300
C1—C6	1.396 (5)	C10—C15	1.395 (7)
C1—H1A	0.9300	C10—C11	1.409 (5)
C2—C3	1.376 (5)	C11—C12	1.386 (6)
C2—H2A	0.9300	C12—C13	1.381 (7)
C3—C4	1.390 (5)	C12—H12A	0.9300
C4—C5	1.373 (5)	C13—C14	1.389 (6)
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.389 (5)	C14—C15	1.388 (6)
C5—H5A	0.9300	C14—H14A	0.9300
C6—C7	1.493 (5)	C15—H15A	0.9300
C7—C8	1.479 (5)
C2—C1—C6	120.5 (3)	C7—C8—H8A	120.2
C2—C1—H1A	119.7	C8—C9—C10	127.4 (4)
C6—C1—H1A	119.7	C8—C9—H9A	116.3
C3—C2—C1	118.6 (3)	C10—C9—H9A	116.3
C3—C2—H2A	120.7	C15—C10—C11	117.2 (4)
C1—C2—H2A	120.7	C15—C10—C9	122.0 (3)
C2—C3—C4	122.0 (4)	C11—C10—C9	120.8 (5)
C2—C3—Br1	119.9 (3)	C12—C11—C10	121.7 (4)
C4—C3—Br1	118.1 (3)	C12—C11—Cl1	117.5 (3)
C5—C4—C3	118.7 (3)	C10—C11—Cl1	120.8 (3)
C5—C4—H4A	120.6	C13—C12—C11	119.8 (4)
C3—C4—H4A	120.6	C13—C12—H12A	120.1
C4—C5—C6	120.9 (3)	C11—C12—H12A	120.1
C4—C5—H5A	119.6	C12—C13—C14	119.7 (4)
C6—C5—H5A	119.6	C12—C13—H13A	120.1
C5—C6—C1	119.2 (3)	C14—C13—H13A	120.1
C5—C6—C7	117.7 (3)	C15—C14—C13	120.4 (4)
C1—C6—C7	123.0 (3)	C15—C14—H14A	119.8
O1—C7—C8	120.9 (4)	C13—C14—H14A	119.8
O1—C7—C6	119.9 (3)	C14—C15—C10	121.2 (4)
C8—C7—C6	119.2 (3)	C14—C15—H15A	119.4
C9—C8—C7	119.5 (3)	C10—C15—H15A	119.4
C9—C8—H8A	120.2
C6—C1—C2—C3	0.1 (6)	C6—C7—C8—C9	173.5 (4)
C1—C2—C3—C4	−0.9 (6)	C7—C8—C9—C10	176.9 (3)
C1—C2—C3—Br1	178.1 (3)	C8—C9—C10—C15	−2.7 (6)
C2—C3—C4—C5	1.1 (6)	C8—C9—C10—C11	179.0 (4)
Br1—C3—C4—C5	−177.9 (3)	C15—C10—C11—C12	−0.3 (5)
C3—C4—C5—C6	−0.7 (6)	C9—C10—C11—C12	178.1 (3)
C4—C5—C6—C1	0.0 (6)	C15—C10—C11—Cl1	179.1 (3)
C4—C5—C6—C7	176.4 (3)	C9—C10—C11—Cl1	−2.5 (5)
C2—C1—C6—C5	0.3 (6)	C10—C11—C12—C13	−0.4 (6)
C2—C1—C6—C7	−175.9 (4)	Cl1—C11—C12—C13	−179.8 (3)
C5—C6—C7—O1	−10.8 (5)	C11—C12—C13—C14	0.7 (6)
C1—C6—C7—O1	165.5 (4)	C12—C13—C14—C15	−0.4 (6)
C5—C6—C7—C8	168.8 (3)	C13—C14—C15—C10	−0.2 (6)
C1—C6—C7—C8	−15.0 (5)	C11—C10—C15—C14	0.6 (5)
O1—C7—C8—C9	−7.0 (6)	C9—C10—C15—C14	−177.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1i	0.93	2.53	3.191 (4)	128
C9—H9A···Cl1	0.93	2.61	3.064 (4)	111
C9—H9A···O1	0.93	2.41	2.765 (5)	102

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O1i	0.93	2.53	3.191 (4)	128
C9—H9A⋯Cl1	0.93	2.61	3.064 (4)	111
C9—H9A⋯O1	0.93	2.41	2.765 (5)	102

Symmetry code: (i) .