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

In the title compound, C(16)H(12)BrFO(2), the dihedral angle between the aromatic rings is 23.75 (12)° and the dihedral angle between the prop-2-en-1-one fragment and the fluorobenzene ring is 20.9 (2)°. In the crystal, only van der Waals interactions occur.

Related literature

For the normal probability plot test, see: Abrahams & Keve (1971 ▶); Cromer (1974 ▶). For the influence of the substituents on the geometry of the phenyl ring, see: Domenicano & Murray-Rust (1979 ▶); Domenicano (1988 ▶). For a closely related structure, see: Dutkiewicz et al. (2011 ▶).

Experimental

Crystal data

C16H12BrFO2

M = 335.17

Monoclinic,

a = 11.056 (2) Å

b = 4.1110 (15) Å

c = 30.825 (5) Å

β = 96.76 (2)°

V = 1391.3 (6) Å3

Z = 4

Mo Kα radiation

μ = 2.96 mm−1

T = 295 K

0.5 × 0.4 × 0.15 mm

Data collection

Agilent Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.507, T max = 1.000

6983 measured reflections

2887 independent reflections

1918 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.092

S = 1.02

2887 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.52 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012505/dn2670sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012505/dn2670Isup2.hkl

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

C16H12BrFO2	F(000) = 672
Mr = 335.17	Dx = 1.600 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2417 reflections
a = 11.056 (2) Å	θ = 3.1–28.0°
b = 4.1110 (15) Å	µ = 2.96 mm−1
c = 30.825 (5) Å	T = 295 K
β = 96.76 (2)°	Prism, colourless
V = 1391.3 (6) Å3	0.5 × 0.4 × 0.15 mm
Z = 4

Agilent Xcalibur Eos diffractometer	2887 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1918 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 16.1544 pixels mm-1	θmax = 28.0°, θmin = 3.1°
ω scans	h = −13→14
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −5→5
Tmin = 0.507, Tmax = 1.000	l = −38→39
6983 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.045P)2] where P = (Fo2 + 2Fc2)/3
2887 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.52 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
C1	0.1287 (3)	0.1073 (8)	0.61784 (11)	0.0453 (9)
O1	0.0290 (2)	0.2293 (7)	0.60968 (8)	0.0649 (7)
C2	0.1926 (3)	0.1062 (8)	0.66297 (11)	0.0427 (8)
H2	0.2639	−0.0139	0.6689	0.051*
C3	0.1509 (3)	0.2716 (8)	0.69512 (11)	0.0397 (8)
H3	0.0814	0.3956	0.6873	0.048*
C4	0.1999 (3)	0.2836 (7)	0.74082 (10)	0.0328 (7)
C5	0.3100 (3)	0.1388 (7)	0.75684 (10)	0.0340 (7)
H5	0.3557	0.0294	0.7379	0.041*
C6	0.3511 (3)	0.1577 (7)	0.80038 (11)	0.0342 (7)
Br6	0.50370 (3)	−0.02669 (8)	0.820926 (12)	0.05081 (15)
C7	0.2842 (3)	0.3147 (7)	0.83016 (10)	0.0370 (8)
O7	0.3326 (2)	0.3123 (6)	0.87212 (7)	0.0539 (7)
C71	0.2665 (4)	0.4821 (10)	0.90272 (13)	0.0834 (15)
H71A	0.1882	0.3821	0.9033	0.125*
H71B	0.2558	0.7053	0.8939	0.125*
H71C	0.3114	0.4722	0.9313	0.125*
C8	0.1740 (3)	0.4534 (7)	0.81422 (12)	0.0434 (8)
H8	0.1263	0.5534	0.8333	0.052*
C9	0.1346 (3)	0.4439 (7)	0.77032 (12)	0.0414 (8)
H9	0.0622	0.5477	0.7600	0.050*
C11	0.1903 (3)	−0.0519 (8)	0.58326 (10)	0.0414 (8)
C12	0.3150 (3)	−0.1039 (9)	0.58687 (12)	0.0549 (10)
H12	0.3634	−0.0397	0.6121	0.066*
C13	0.3682 (4)	−0.2492 (10)	0.55362 (13)	0.0653 (11)
H13	0.4519	−0.2840	0.5562	0.078*
C14	0.2958 (4)	−0.3405 (10)	0.51699 (13)	0.0647 (11)
F14	0.3475 (3)	−0.4875 (6)	0.48435 (9)	0.1010 (9)
C15	0.1731 (4)	−0.2938 (10)	0.51172 (13)	0.0664 (11)
H15	0.1257	−0.3590	0.4863	0.080*
C16	0.1211 (3)	−0.1476 (10)	0.54502 (12)	0.0579 (10)
H16	0.0375	−0.1121	0.5418	0.069*

	U11	U22	U33	U12	U13	U23
C1	0.044 (2)	0.050 (2)	0.040 (2)	−0.0048 (18)	−0.0020 (16)	0.0113 (17)
O1	0.0470 (15)	0.096 (2)	0.0495 (17)	0.0107 (15)	−0.0012 (12)	0.0108 (15)
C2	0.040 (2)	0.0474 (19)	0.040 (2)	−0.0022 (16)	0.0025 (16)	0.0054 (17)
C3	0.0342 (18)	0.0413 (19)	0.043 (2)	−0.0046 (15)	0.0030 (15)	0.0054 (17)
C4	0.0280 (16)	0.0331 (17)	0.0376 (19)	−0.0056 (14)	0.0059 (14)	0.0018 (15)
C5	0.0352 (18)	0.0330 (16)	0.0360 (19)	−0.0028 (15)	0.0135 (14)	−0.0030 (15)
C6	0.0311 (17)	0.0309 (16)	0.041 (2)	−0.0039 (14)	0.0074 (14)	−0.0027 (15)
Br6	0.0406 (2)	0.0546 (2)	0.0557 (2)	0.01012 (18)	−0.00083 (15)	−0.00365 (19)
C7	0.0423 (19)	0.0339 (17)	0.036 (2)	0.0000 (16)	0.0111 (15)	0.0006 (15)
O7	0.0669 (17)	0.0631 (16)	0.0318 (15)	0.0137 (13)	0.0064 (12)	−0.0071 (12)
C71	0.125 (4)	0.090 (3)	0.037 (2)	0.046 (3)	0.014 (2)	−0.013 (2)
C8	0.0422 (19)	0.041 (2)	0.050 (2)	0.0063 (17)	0.0174 (16)	−0.0053 (17)
C9	0.0318 (17)	0.0398 (18)	0.052 (2)	0.0035 (15)	0.0049 (15)	0.0017 (17)
C11	0.048 (2)	0.0445 (19)	0.0297 (18)	−0.0072 (17)	−0.0026 (15)	0.0058 (16)
C12	0.060 (2)	0.069 (2)	0.034 (2)	−0.004 (2)	−0.0011 (17)	−0.0014 (19)
C13	0.062 (3)	0.084 (3)	0.049 (3)	0.009 (2)	0.006 (2)	−0.003 (2)
C14	0.097 (4)	0.059 (2)	0.037 (2)	0.002 (3)	0.009 (2)	−0.003 (2)
F14	0.141 (2)	0.112 (2)	0.0519 (16)	0.0258 (17)	0.0209 (15)	−0.0175 (15)
C15	0.086 (3)	0.074 (3)	0.036 (2)	−0.015 (3)	−0.007 (2)	−0.004 (2)
C16	0.053 (2)	0.075 (3)	0.043 (2)	−0.011 (2)	−0.0043 (18)	0.006 (2)

C1—O1	1.210 (4)	C71—H71B	0.9600
C1—C11	1.483 (5)	C71—H71C	0.9600
C1—C2	1.484 (5)	C8—C9	1.372 (5)
C2—C3	1.328 (4)	C8—H8	0.9300
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.449 (4)	C11—C16	1.385 (5)
C3—H3	0.9300	C11—C12	1.387 (4)
C4—C9	1.391 (4)	C12—C13	1.377 (5)
C4—C5	1.393 (4)	C12—H12	0.9300
C5—C6	1.367 (4)	C13—C14	1.358 (5)
C5—H5	0.9300	C13—H13	0.9300
C6—C7	1.402 (4)	C14—F14	1.357 (4)
C6—Br6	1.890 (3)	C14—C15	1.361 (5)
C7—O7	1.340 (4)	C15—C16	1.372 (5)
C7—C8	1.383 (4)	C15—H15	0.9300
O7—C71	1.440 (4)	C16—H16	0.9300
C71—H71A	0.9600
O1—C1—C11	121.2 (3)	H71A—C71—H71C	109.5
O1—C1—C2	121.1 (3)	H71B—C71—H71C	109.5
C11—C1—C2	117.7 (3)	C9—C8—C7	120.1 (3)
C3—C2—C1	122.0 (3)	C9—C8—H8	119.9
C3—C2—H2	119.0	C7—C8—H8	119.9
C1—C2—H2	119.0	C8—C9—C4	122.0 (3)
C2—C3—C4	128.3 (3)	C8—C9—H9	119.0
C2—C3—H3	115.8	C4—C9—H9	119.0
C4—C3—H3	115.8	C16—C11—C12	118.0 (3)
C9—C4—C5	118.0 (3)	C16—C11—C1	118.9 (3)
C9—C4—C3	119.2 (3)	C12—C11—C1	123.1 (3)
C5—C4—C3	122.8 (3)	C13—C12—C11	121.0 (3)
C6—C5—C4	119.9 (3)	C13—C12—H12	119.5
C6—C5—H5	120.0	C11—C12—H12	119.5
C4—C5—H5	120.0	C14—C13—C12	118.5 (4)
C5—C6—C7	122.0 (3)	C14—C13—H13	120.8
C5—C6—Br6	119.1 (2)	C12—C13—H13	120.8
C7—C6—Br6	118.9 (2)	F14—C14—C13	118.8 (4)
O7—C7—C8	125.5 (3)	F14—C14—C15	118.4 (4)
O7—C7—C6	116.6 (3)	C13—C14—C15	122.8 (4)
C8—C7—C6	117.9 (3)	C14—C15—C16	118.1 (4)
C7—O7—C71	117.0 (3)	C14—C15—H15	120.9
O7—C71—H71A	109.5	C16—C15—H15	120.9
O7—C71—H71B	109.5	C15—C16—C11	121.6 (4)
H71A—C71—H71B	109.5	C15—C16—H16	119.2
O7—C71—H71C	109.5	C11—C16—H16	119.2
O1—C1—C2—C3	−8.4 (5)	C7—C8—C9—C4	3.2 (5)
C11—C1—C2—C3	172.8 (3)	C5—C4—C9—C8	−2.0 (4)
C1—C2—C3—C4	177.2 (3)	C3—C4—C9—C8	177.6 (3)
C2—C3—C4—C9	−172.8 (3)	O1—C1—C11—C16	−19.2 (5)
C2—C3—C4—C5	6.7 (5)	C2—C1—C11—C16	159.6 (3)
C9—C4—C5—C6	−0.2 (4)	O1—C1—C11—C12	159.3 (3)
C3—C4—C5—C6	−179.7 (3)	C2—C1—C11—C12	−21.8 (5)
C4—C5—C6—C7	1.2 (4)	C16—C11—C12—C13	−0.6 (5)
C4—C5—C6—Br6	−177.6 (2)	C1—C11—C12—C13	−179.2 (3)
C5—C6—C7—O7	178.8 (3)	C11—C12—C13—C14	0.1 (6)
Br6—C6—C7—O7	−2.3 (4)	C12—C13—C14—F14	−179.2 (3)
C5—C6—C7—C8	−0.2 (5)	C12—C13—C14—C15	0.2 (6)
Br6—C6—C7—C8	178.7 (2)	F14—C14—C15—C16	179.4 (4)
C8—C7—O7—C71	−3.1 (5)	C13—C14—C15—C16	0.1 (6)
C6—C7—O7—C71	178.0 (3)	C14—C15—C16—C11	−0.6 (6)
O7—C7—C8—C9	179.2 (3)	C12—C11—C16—C15	0.9 (6)
C6—C7—C8—C9	−2.0 (5)	C1—C11—C16—C15	179.5 (3)