2,3-Dibromo-1,3-bis-(4-fluoro-phen-yl)propan-1-one.

In the title compound, C(15)H(10)Br(2)F(2)O, the dihedral angle between the two 3-fluoro-substituted benzene rings is 5.7 (5)°. The two bromine substituents on the chalcone moiety are close to anti as the Br-C-C-Br torsion angle is 176.9 (7)°. Weak C-Br⋯π inter-actions may contribute to the crystal stability.

Related literature

For bromo substitution of non-linerar optical (NLO) compounds, see: Uchida et al. (1998 ▶); Tam et al. (1989 ▶); Indira et al. (2002 ▶). For NLO first-order hyperpolarizabilities, see: Zhao et al. (2002 ▶). For related structures, see: Narayana et al. (2007 ▶); Sarojini et al. (2007 ▶); Yathirajan et al. (2007 ▶); Butcher et al. (2006 ▶).

Experimental

Crystal data

C15H10Br2F2O

M = 404.05

Triclinic,

a = 5.7381 (13) Å

b = 9.909 (2) Å

c = 12.575 (3) Å

α = 75.324 (3)°

β = 87.472 (3)°

γ = 82.300 (3)°

V = 685.4 (3) Å3

Z = 2

Mo Kα radiation

μ = 5.93 mm−1

T = 100 K

0.55 × 0.30 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.329, T max = 0.746

8841 measured reflections

4008 independent reflections

3408 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.079

S = 1.21

4008 reflections

181 parameters

H-atom parameters constrained

Δρmax = 1.08 e Å−3

Δρmin = −0.87 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810026905/tk2690sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026905/tk2690Isup2.hkl

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

C15H10Br2F2O	Z = 2
Mr = 404.05	F(000) = 392
Triclinic, P1	Dx = 1.958 Mg m−3
Hall symbol: -P 1	Melting point: 443 K
a = 5.7381 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.909 (2) Å	Cell parameters from 3859 reflections
c = 12.575 (3) Å	θ = 2.4–31.2°
α = 75.324 (3)°	µ = 5.93 mm−1
β = 87.472 (3)°	T = 100 K
γ = 82.300 (3)°	Block, colourless
V = 685.4 (3) Å3	0.55 × 0.30 × 0.25 mm

Bruker APEXII CCD diffractometer	4008 independent reflections
Radiation source: fine-focus sealed tube	3408 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω scans	θmax = 31.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −8→8
Tmin = 0.329, Tmax = 0.746	k = −14→14
8841 measured reflections	l = −17→17

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H-atom parameters constrained
S = 1.21	w = 1/[σ2(Fo2) + (0.0334P)2] where P = (Fo2 + 2Fc2)/3
4008 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 1.08 e Å−3
0 restraints	Δρmin = −0.87 e Å−3

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	0.01364 (4)	0.64928 (2)	0.325242 (18)	0.01732 (7)
Br3	0.63722 (4)	0.41938 (2)	0.166955 (18)	0.01767 (7)
F3	0.2805 (3)	0.01545 (14)	0.61742 (12)	0.0256 (3)
F4	−0.1808 (3)	0.97463 (15)	−0.24671 (12)	0.0269 (3)
O1	0.4729 (3)	0.76521 (17)	0.16467 (14)	0.0197 (3)
C1	0.1701 (4)	0.1693 (2)	0.44729 (19)	0.0198 (5)
H1	0.0491	0.1177	0.4421	0.024*
C2	0.3155 (4)	0.1313 (2)	0.53742 (19)	0.0177 (5)
C3	0.4942 (4)	0.2065 (2)	0.5500 (2)	0.0199 (5)
H3	0.5871	0.1797	0.6124	0.024*
C4	0.5301 (4)	0.3239 (2)	0.46579 (19)	0.0189 (5)
H4	0.6503	0.3759	0.4716	0.023*
C5	0.3885 (4)	0.3646 (2)	0.37295 (18)	0.0157 (4)
C6	0.2097 (4)	0.2867 (2)	0.36490 (19)	0.0188 (5)
H6	0.1147	0.3136	0.3031	0.023*
C7	0.4417 (4)	0.4886 (2)	0.28267 (18)	0.0152 (4)
H7	0.5313	0.5473	0.3131	0.018*
C24	−0.1493 (4)	0.7950 (2)	−0.08429 (19)	0.0180 (4)
H24	−0.2841	0.7630	−0.1019	0.022*
C25	−0.0292 (4)	0.7287 (2)	0.01293 (18)	0.0150 (4)
H25	−0.0851	0.6520	0.0613	0.018*
C26	0.1738 (4)	0.7767 (2)	0.03802 (18)	0.0133 (4)
C27	0.2560 (4)	0.8922 (2)	−0.03527 (18)	0.0146 (4)
H27	0.3918	0.9243	−0.0188	0.018*
C28	0.1387 (4)	0.9599 (2)	−0.13229 (19)	0.0178 (5)
H28	0.1938	1.0366	−0.1811	0.021*
C29	−0.0623 (4)	0.9097 (2)	−0.15370 (18)	0.0176 (5)
C30	0.3079 (4)	0.7134 (2)	0.14074 (18)	0.0146 (4)
C31	0.2346 (4)	0.5802 (2)	0.22021 (18)	0.0155 (4)
H31	0.1558	0.5266	0.1802	0.019*

	U11	U22	U33	U12	U13	U23
Br1	0.01593 (12)	0.01512 (11)	0.02036 (13)	0.00004 (8)	0.00191 (8)	−0.00485 (8)
Br3	0.01936 (12)	0.01393 (11)	0.02088 (13)	−0.00394 (8)	0.00569 (9)	−0.00655 (8)
F3	0.0373 (9)	0.0182 (7)	0.0176 (7)	−0.0072 (6)	0.0014 (6)	0.0037 (5)
F4	0.0366 (9)	0.0234 (7)	0.0175 (7)	0.0027 (6)	−0.0117 (6)	−0.0004 (6)
O1	0.0211 (8)	0.0162 (7)	0.0228 (9)	−0.0080 (6)	−0.0057 (7)	−0.0027 (6)
C1	0.0231 (12)	0.0161 (10)	0.0205 (12)	−0.0076 (9)	0.0003 (9)	−0.0027 (9)
C2	0.0228 (12)	0.0128 (10)	0.0153 (10)	−0.0001 (8)	0.0022 (8)	−0.0009 (8)
C3	0.0228 (12)	0.0180 (11)	0.0171 (11)	0.0004 (9)	−0.0052 (9)	−0.0015 (9)
C4	0.0208 (11)	0.0172 (10)	0.0193 (11)	−0.0033 (8)	−0.0035 (9)	−0.0048 (9)
C5	0.0194 (11)	0.0122 (9)	0.0151 (10)	−0.0018 (8)	−0.0002 (8)	−0.0026 (8)
C6	0.0220 (11)	0.0165 (10)	0.0168 (11)	−0.0048 (8)	−0.0046 (9)	−0.0004 (8)
C7	0.0159 (10)	0.0138 (9)	0.0170 (11)	−0.0023 (8)	−0.0003 (8)	−0.0057 (8)
C24	0.0165 (11)	0.0177 (10)	0.0213 (12)	−0.0017 (8)	−0.0026 (9)	−0.0074 (9)
C25	0.0171 (10)	0.0132 (9)	0.0150 (10)	−0.0036 (8)	0.0010 (8)	−0.0035 (8)
C26	0.0166 (10)	0.0099 (9)	0.0134 (10)	−0.0002 (7)	−0.0001 (8)	−0.0036 (7)
C27	0.0164 (10)	0.0107 (9)	0.0181 (11)	−0.0026 (8)	0.0029 (8)	−0.0061 (8)
C28	0.0257 (12)	0.0111 (9)	0.0150 (11)	−0.0011 (8)	0.0018 (9)	−0.0013 (8)
C29	0.0234 (11)	0.0145 (10)	0.0134 (10)	0.0061 (8)	−0.0028 (8)	−0.0046 (8)
C30	0.0170 (10)	0.0110 (9)	0.0163 (10)	−0.0030 (8)	−0.0011 (8)	−0.0036 (8)
C31	0.0188 (11)	0.0127 (9)	0.0151 (10)	−0.0041 (8)	−0.0019 (8)	−0.0022 (8)

Br1—C31	1.974 (2)	C7—C31	1.511 (3)
Br3—C7	2.001 (2)	C7—H7	0.9800
F3—C2	1.352 (2)	C24—C29	1.383 (3)
F4—C29	1.347 (2)	C24—C25	1.395 (3)
O1—C30	1.218 (3)	C24—H24	0.9300
C1—C2	1.380 (3)	C25—C26	1.392 (3)
C1—C6	1.384 (3)	C25—H25	0.9300
C1—H1	0.9300	C26—C27	1.398 (3)
C2—C3	1.383 (3)	C26—C30	1.484 (3)
C3—C4	1.392 (3)	C27—C28	1.389 (3)
C3—H3	0.9300	C27—H27	0.9300
C4—C5	1.394 (3)	C28—C29	1.378 (3)
C4—H4	0.9300	C28—H28	0.9300
C5—C6	1.386 (3)	C30—C31	1.537 (3)
C5—C7	1.502 (3)	C31—H31	0.9800
C6—H6	0.9300
C2—C1—C6	118.1 (2)	C25—C24—H24	120.9
C2—C1—H1	121.0	C24—C25—C26	120.4 (2)
C6—C1—H1	121.0	C24—C25—H25	119.8
F3—C2—C1	118.4 (2)	C26—C25—H25	119.8
F3—C2—C3	118.5 (2)	C25—C26—C27	119.3 (2)
C1—C2—C3	123.0 (2)	C25—C26—C30	123.47 (19)
C2—C3—C4	117.6 (2)	C27—C26—C30	117.3 (2)
C2—C3—H3	121.2	C28—C27—C26	121.2 (2)
C4—C3—H3	121.2	C28—C27—H27	119.4
C5—C4—C3	120.9 (2)	C26—C27—H27	119.4
C5—C4—H4	119.5	C29—C28—C27	117.7 (2)
C3—C4—H4	119.5	C29—C28—H28	121.1
C6—C5—C4	119.2 (2)	C27—C28—H28	121.1
C6—C5—C7	122.1 (2)	F4—C29—C28	118.8 (2)
C4—C5—C7	118.6 (2)	F4—C29—C24	118.0 (2)
C1—C6—C5	121.1 (2)	C28—C29—C24	123.2 (2)
C1—C6—H6	119.5	O1—C30—C26	121.82 (19)
C5—C6—H6	119.5	O1—C30—C31	118.95 (19)
C5—C7—C31	116.96 (19)	C26—C30—C31	119.22 (19)
C5—C7—Br3	108.97 (15)	C7—C31—C30	111.97 (19)
C31—C7—Br3	103.93 (16)	C7—C31—Br1	108.95 (16)
C5—C7—H7	108.9	C30—C31—Br1	105.03 (14)
C31—C7—H7	108.9	C7—C31—H31	110.3
Br3—C7—H7	108.9	C30—C31—H31	110.3
C29—C24—C25	118.2 (2)	Br1—C31—H31	110.3
C29—C24—H24	120.9
C6—C1—C2—F3	−178.9 (2)	C30—C26—C27—C28	−178.6 (2)
C6—C1—C2—C3	1.5 (4)	C26—C27—C28—C29	0.3 (3)
F3—C2—C3—C4	178.8 (2)	C27—C28—C29—F4	179.2 (2)
C1—C2—C3—C4	−1.5 (4)	C27—C28—C29—C24	−0.9 (4)
C2—C3—C4—C5	0.8 (4)	C25—C24—C29—F4	−179.1 (2)
C3—C4—C5—C6	0.0 (4)	C25—C24—C29—C28	1.1 (4)
C3—C4—C5—C7	−177.5 (2)	C25—C26—C30—O1	−173.5 (2)
C2—C1—C6—C5	−0.6 (4)	C27—C26—C30—O1	5.2 (3)
C4—C5—C6—C1	−0.1 (4)	C25—C26—C30—C31	5.4 (3)
C7—C5—C6—C1	177.4 (2)	C27—C26—C30—C31	−175.9 (2)
C6—C5—C7—C31	36.4 (3)	C5—C7—C31—C30	172.58 (18)
C4—C5—C7—C31	−146.1 (2)	Br3—C7—C31—C30	−67.3 (2)
C6—C5—C7—Br3	−81.0 (2)	C5—C7—C31—Br1	56.8 (2)
C4—C5—C7—Br3	96.5 (2)	Br3—C7—C31—Br1	176.97 (9)
C29—C24—C25—C26	−0.6 (3)	O1—C30—C31—C7	−31.3 (3)
C24—C25—C26—C27	0.0 (3)	C26—C30—C31—C7	149.7 (2)
C24—C25—C26—C30	178.7 (2)	O1—C30—C31—Br1	86.8 (2)
C25—C26—C27—C28	0.1 (3)	C26—C30—C31—Br1	−92.2 (2)

Y—X···Cg	X···Cg	Y···Cg	Y—X···Cg
C8—Br1···Cg1i	3.650 (7)	5.617 (2)	174
C7—Br3···Cg2ii	3.479 (6)	5.341 (1)	153

Table 1

Y—X⋯Cg inter­actions (Å)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

Y—X⋯Cg	X⋯Cg	Y⋯Cg	Y—X⋯Cg
C8—Br1⋯Cg1i	3.650 (7)	5.617 (2)	174
C7—Br3⋯Cg2ii	3.479 (6)	5.341 (1)	153

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