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

The title compound, C(15)H(10)BrFO, is isostructural with (2E)-1-(4-chloro-phen-yl)-3-(4-fluoro-phen-yl)prop-2-en-1-one [Qiu et al. (2006 ▶). Acta Cryst. E62, o3525-o3526], but the structures of other dihalogen analogues, without fluorine, are different, although they are also isostructural within the series. The mol-ecule is approximately flat, the dihedral angle between the ring planes being 8.49 (13)°. In the crystal structure, inter-molecular C-H⋯O, C-H⋯F and C-H⋯Br hydrogen bonds link mol-ecules into V-shaped ribbons running parallel to [101] and stacked with an inter-planar distance of approximately 3.53 Å (centroid-vcentroid distance = 3.857 Å)..

Related literature

For general background to chalcones, see: Dhar (1981 ▶); Goto et al. (1991 ▶); Uchida et al. (1998 ▶); Indira et al. (2002 ▶); Sarojini et al. (2006 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For the isostructurality index, see: Kálmán et al. (1991 ▶). For related halogen derivatives, see: Ng, Razak, et al. (2006 ▶); Ng, Shettigar et al. (2006 ▶); Qiu et al. (2006 ▶); Wang et al. (2005 ▶); Yang et al. (2006 ▶).

Experimental

Crystal data

C15H10BrFO

M = 305.14

Monoclinic,

a = 4.0060 (5) Å

b = 23.1253 (12) Å

c = 13.4933 (9) Å

β = 96.344 (6)°

V = 1242.36 (19) Å3

Z = 4

Cu Kα radiation

μ = 4.49 mm−1

T = 295 K

0.4 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction SuperNova (single source at offset) Atlas diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.386, T max = 1.000

4548 measured reflections

2435 independent reflections

2299 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.116

S = 1.12

2435 reflections

203 parameters

All H-atom parameters refined

Δρmax = 0.73 e Å−3

Δρmin = −0.50 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Siemens, 1989 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810015485/rz2439sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015485/rz2439Isup2.hkl

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

C15H10BrFO	F(000) = 608
Mr = 305.14	Dx = 1.631 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 4020 reflections
a = 4.0060 (5) Å	θ = 3.3–75.1°
b = 23.1253 (12) Å	µ = 4.49 mm−1
c = 13.4933 (9) Å	T = 295 K
β = 96.344 (6)°	Prism, colourless
V = 1242.36 (19) Å3	0.4 × 0.2 × 0.1 mm
Z = 4

Oxford Diffraction SuperNova (single source at offset) Atlas diffractometer	2435 independent reflections
Radiation source: Nova (Cu) X-ray Source	2299 reflections with I > 2σ(I)
mirror	Rint = 0.018
Detector resolution: 5.2679 pixels mm-1	θmax = 75.2°, θmin = 3.8°
ω–scan	h = −3→5
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −28→27
Tmin = 0.386, Tmax = 1.000	l = −16→14
4548 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	All H-atom parameters refined
S = 1.12	w = 1/[σ2(Fo2) + (0.0695P)2 + 0.5227P] where P = (Fo2 + 2Fc2)/3
2435 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.73 e Å−3
0 restraints	Δρmin = −0.50 e Å−3

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 > 2σ(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	0.64900 (8)	0.251119 (13)	0.06664 (2)	0.06378 (18)
F1	0.8178 (6)	0.08073 (9)	0.99300 (12)	0.0843 (6)
C1	0.7067 (7)	0.07919 (13)	0.89344 (19)	0.0548 (6)
C2	0.5320 (8)	0.03177 (13)	0.85733 (18)	0.0544 (6)
H2	0.507 (9)	−0.0022 (15)	0.902 (3)	0.073 (10)*
C3	0.4195 (7)	0.03031 (11)	0.75622 (18)	0.0482 (6)
H3	0.297 (9)	−0.0027 (13)	0.722 (3)	0.073 (10)*
C4	0.4894 (6)	0.07548 (10)	0.69363 (16)	0.0400 (5)
C5	0.6687 (7)	0.12313 (12)	0.73467 (19)	0.0489 (6)
H5	0.725 (10)	0.1543 (15)	0.699 (3)	0.078 (10)*
C6	0.7766 (8)	0.12519 (14)	0.8363 (2)	0.0572 (7)
H6	0.914 (9)	0.1585 (15)	0.870 (3)	0.078 (11)*
C7	0.3685 (6)	0.07087 (10)	0.58732 (16)	0.0417 (5)
H7	0.190 (7)	0.0422 (13)	0.571 (2)	0.051 (8)*
C8	0.4515 (6)	0.10426 (10)	0.51437 (17)	0.0423 (5)
H8	0.627 (7)	0.1331 (13)	0.525 (2)	0.053 (8)*
O9	0.1120 (5)	0.05436 (8)	0.38882 (13)	0.0589 (5)
C9	0.3051 (6)	0.09403 (10)	0.41020 (17)	0.0401 (5)
C10	0.3943 (5)	0.13412 (10)	0.32965 (16)	0.0368 (5)
C11	0.2928 (6)	0.11865 (11)	0.23070 (17)	0.0426 (5)
H11	0.184 (8)	0.0847 (13)	0.217 (2)	0.060 (8)*
C12	0.3662 (6)	0.15324 (11)	0.15256 (17)	0.0462 (5)
H12	0.294 (7)	0.1403 (12)	0.083 (2)	0.054 (8)*
C13	0.5401 (6)	0.20384 (11)	0.17354 (17)	0.0427 (5)
C14	0.6406 (6)	0.22126 (11)	0.27017 (19)	0.0461 (5)
H14	0.716 (12)	0.2556 (13)	0.277 (3)	0.075 (13)*
C15	0.5676 (6)	0.18557 (10)	0.34762 (17)	0.0436 (5)
H15	0.646 (8)	0.1983 (13)	0.419 (2)	0.059 (8)*

	U11	U22	U33	U12	U13	U23
Br1	0.0534 (3)	0.0764 (3)	0.0619 (3)	0.00176 (12)	0.00788 (16)	0.03331 (14)
F1	0.1142 (16)	0.1010 (15)	0.0343 (8)	−0.0239 (12)	−0.0074 (9)	−0.0034 (8)
C1	0.0614 (16)	0.0684 (16)	0.0341 (12)	−0.0027 (13)	0.0027 (10)	−0.0040 (11)
C2	0.0702 (17)	0.0569 (15)	0.0362 (12)	−0.0062 (13)	0.0067 (11)	0.0058 (11)
C3	0.0589 (14)	0.0470 (13)	0.0386 (11)	−0.0078 (11)	0.0049 (10)	0.0009 (10)
C4	0.0422 (12)	0.0436 (11)	0.0344 (10)	0.0012 (9)	0.0052 (8)	0.0013 (9)
C5	0.0573 (15)	0.0465 (13)	0.0429 (12)	−0.0077 (11)	0.0059 (10)	0.0020 (10)
C6	0.0648 (17)	0.0624 (16)	0.0437 (13)	−0.0148 (13)	0.0031 (12)	−0.0074 (12)
C7	0.0449 (12)	0.0435 (11)	0.0365 (11)	−0.0004 (9)	0.0036 (9)	−0.0011 (9)
C8	0.0441 (12)	0.0455 (12)	0.0368 (11)	−0.0024 (10)	0.0021 (9)	−0.0005 (9)
O9	0.0744 (13)	0.0577 (11)	0.0428 (9)	−0.0259 (10)	−0.0017 (8)	0.0021 (8)
C9	0.0440 (12)	0.0411 (11)	0.0351 (10)	−0.0001 (9)	0.0038 (8)	−0.0003 (9)
C10	0.0357 (11)	0.0393 (11)	0.0349 (10)	0.0039 (8)	0.0019 (8)	−0.0005 (8)
C11	0.0483 (13)	0.0418 (12)	0.0366 (11)	−0.0031 (9)	0.0000 (9)	−0.0012 (9)
C12	0.0499 (13)	0.0536 (13)	0.0337 (11)	0.0025 (10)	−0.0014 (9)	0.0032 (9)
C13	0.0360 (11)	0.0487 (12)	0.0432 (11)	0.0063 (9)	0.0037 (8)	0.0111 (9)
C14	0.0435 (12)	0.0430 (13)	0.0513 (13)	−0.0063 (10)	0.0027 (10)	0.0005 (10)
C15	0.0474 (12)	0.0454 (12)	0.0372 (11)	−0.0032 (10)	0.0008 (9)	−0.0032 (9)

Br1—C13	1.899 (2)	C8—C9	1.481 (3)
F1—C1	1.368 (3)	C8—H8	0.97 (3)
C1—C6	1.361 (4)	O9—C9	1.214 (3)
C1—C2	1.362 (4)	C9—C10	1.501 (3)
C2—C3	1.389 (3)	C10—C15	1.385 (3)
C2—H2	1.00 (3)	C10—C11	1.399 (3)
C3—C4	1.391 (3)	C11—C12	1.381 (3)
C3—H3	0.99 (3)	C11—H11	0.91 (3)
C4—C5	1.396 (3)	C12—C13	1.375 (4)
C4—C7	1.466 (3)	C12—H12	1.00 (3)
C5—C6	1.392 (4)	C13—C14	1.381 (3)
C5—H5	0.91 (4)	C14—C15	1.388 (3)
C6—H6	1.02 (4)	C14—H14	0.85 (3)
C7—C8	1.322 (3)	C15—H15	1.02 (3)
C7—H7	0.98 (3)
C6—C1—C2	123.8 (2)	C9—C8—H8	117.1 (18)
C6—C1—F1	118.1 (3)	O9—C9—C8	121.4 (2)
C2—C1—F1	118.1 (3)	O9—C9—C10	119.4 (2)
C1—C2—C3	118.0 (2)	C8—C9—C10	119.2 (2)
C1—C2—H2	119.8 (19)	C15—C10—C11	118.3 (2)
C3—C2—H2	122.0 (19)	C15—C10—C9	123.94 (19)
C2—C3—C4	120.9 (2)	C11—C10—C9	117.8 (2)
C2—C3—H3	124 (2)	C12—C11—C10	121.1 (2)
C4—C3—H3	115 (2)	C12—C11—H11	119 (2)
C3—C4—C5	118.8 (2)	C10—C11—H11	120 (2)
C3—C4—C7	118.2 (2)	C13—C12—C11	118.8 (2)
C5—C4—C7	123.0 (2)	C13—C12—H12	122.5 (17)
C6—C5—C4	120.5 (2)	C11—C12—H12	118.7 (17)
C6—C5—H5	115 (2)	C12—C13—C14	122.0 (2)
C4—C5—H5	124 (2)	C12—C13—Br1	119.16 (18)
C1—C6—C5	118.1 (3)	C14—C13—Br1	118.80 (19)
C1—C6—H6	118 (2)	C13—C14—C15	118.3 (2)
C5—C6—H6	124 (2)	C13—C14—H14	116 (3)
C8—C7—C4	127.1 (2)	C15—C14—H14	125 (3)
C8—C7—H7	118.0 (16)	C10—C15—C14	121.5 (2)
C4—C7—H7	114.6 (16)	C10—C15—H15	120.5 (17)
C7—C8—C9	120.5 (2)	C14—C15—H15	118.0 (17)
C7—C8—H8	122.0 (18)
C6—C1—C2—C3	0.1 (5)	O9—C9—C10—C15	169.3 (2)
F1—C1—C2—C3	−180.0 (3)	C8—C9—C10—C15	−9.8 (3)
C1—C2—C3—C4	1.2 (4)	O9—C9—C10—C11	−10.0 (3)
C2—C3—C4—C5	−1.5 (4)	C8—C9—C10—C11	170.8 (2)
C2—C3—C4—C7	179.0 (2)	C15—C10—C11—C12	0.7 (4)
C3—C4—C5—C6	0.3 (4)	C9—C10—C11—C12	−179.8 (2)
C7—C4—C5—C6	179.9 (3)	C10—C11—C12—C13	−0.4 (4)
C2—C1—C6—C5	−1.3 (5)	C11—C12—C13—C14	−0.6 (4)
F1—C1—C6—C5	178.9 (3)	C11—C12—C13—Br1	178.96 (18)
C4—C5—C6—C1	1.0 (5)	C12—C13—C14—C15	1.3 (4)
C3—C4—C7—C8	−168.8 (3)	Br1—C13—C14—C15	−178.27 (18)
C5—C4—C7—C8	11.6 (4)	C11—C10—C15—C14	0.0 (4)
C4—C7—C8—C9	−179.7 (2)	C9—C10—C15—C14	−179.4 (2)
C7—C8—C9—O9	−1.5 (4)	C13—C14—C15—C10	−1.0 (4)
C7—C8—C9—C10	177.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O9i	0.98 (3)	2.62 (3)	3.512 (3)	151 (2)
C3—H3···O9i	0.99 (3)	2.41 (3)	3.358 (3)	160 (2)
C15—H15···Br1ii	1.02 (3)	2.92 (3)	3.845 (2)	151 (2)
C12—H12···F1iii	1.00 (3)	2.55 (3)	3.351 (3)	137 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O9i	0.98 (3)	2.62 (3)	3.512 (3)	151 (2)
C3—H3⋯O9i	0.99 (3)	2.41 (3)	3.358 (3)	160 (2)
C15—H15⋯Br1ii	1.02 (3)	2.92 (3)	3.845 (2)	151 (2)
C12—H12⋯F1iii	1.00 (3)	2.55 (3)	3.351 (3)	137 (2)

Symmetry codes: (i) ; (ii) ; (iii) .