Crystal structure of (2E)-1-(5-bromo-thio-phen-2-yl)-3-(2-chloro-phen-yl)prop-2-en-1-one.

In the title compound, C13H8BrClOS, the thienyl ring is not coplanar with the benzene ring, their planes forming a dihedral angle of 13.2 (4)°. In the crystal, mol-ecules stack along the a axis, with the inter-planar separation between thienyl rings and between benzene rings being 3.925 (6) Å. The sample is an inversion twin.

Related literature

For general background to chalcones, see: Lin et al. (2001 ▸); Horng et al. (2003 ▸); López et al. (2001 ▸); Liu et al. (2003 ▸). For related crystal structures, see: Liang et al. (2011 ▸); Alex et al. (1993 ▸); Li & Su (1993 ▸).

Experimental

Crystal data

C13H8BrClOS

M = 327.61

Orthorhombic,

a = 3.9247 (19) Å

b = 11.549 (6) Å

c = 28.111 (14) Å

V = 1274.1 (11) Å3

Z = 4

Mo Kα radiation

μ = 3.58 mm−1

T = 293 K

0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: ψ scan (SADABS; Sheldrick, 2007 ▸) T min = 0.770, T max = 1.000

12995 measured reflections

3007 independent reflections

2096 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.137

S = 1.10

3007 reflections

155 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.79 e Å−3

Δρmin = −0.33 e Å−3

Absolute structure: refined as an inversion twin

Absolute structure parameter: 0.15 (3)

Data collection: SMART (Bruker, 2001 ▸); cell refinement: SAINT (Bruker, 2001 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: SHELXL2014.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015021155/tk5406sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015021155/tk5406Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015021155/tk5406Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015021155/tk5406fig1.tif

The mol­ecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level.

CCDC reference: 1435865

Additional supporting information: crystallographic information; 3D view; checkCIF report

C13H8BrClOS	Dx = 1.708 Mg m−3
Mr = 327.61	Melting point: 342 K
Orthorhombic, Pc21b	Mo Kα radiation, λ = 0.71073 Å
a = 3.9247 (19) Å	Cell parameters from 3007 reflections
b = 11.549 (6) Å	θ = 2.3–28.0°
c = 28.111 (14) Å	µ = 3.58 mm−1
V = 1274.1 (11) Å3	T = 293 K
Z = 4	Prism, colourless
F(000) = 648	0.24 × 0.20 × 0.12 mm

Bruker SMART CCD area-detector diffractometer	3007 independent reflections
Radiation source: fine-focus sealed tube	2096 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
ω and φ scans	θmax = 28.0°, θmin = 2.3°
Absorption correction: ψ scan (SADABS; Sheldrick, 2007)	h = −5→5
Tmin = 0.770, Tmax = 1.000	k = −15→14
12995 measured reflections	l = −37→36

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.062	w = 1/[σ2(Fo2) + (0.0565P)2 + 0.585P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.137	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.79 e Å−3
3007 reflections	Δρmin = −0.33 e Å−3
155 parameters	Absolute structure: refined as an inversion twin
1 restraint	Absolute structure parameter: 0.15 (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. Refined as a 2-component inversion twin.

	x	y	z	Uiso*/Ueq
Br1	0.8042 (2)	0.11487 (13)	0.17078 (3)	0.0615 (4)
S2	0.5184 (8)	0.2199 (2)	0.07773 (9)	0.0516 (7)
Cl2	−0.0696 (11)	0.3138 (3)	−0.17931 (10)	0.0789 (10)
O4	0.200 (2)	0.2992 (7)	−0.0100 (3)	0.072 (2)
C5	0.617 (2)	0.1001 (11)	0.1095 (3)	0.045 (2)
C6	0.541 (3)	0.0007 (10)	0.0881 (4)	0.056 (3)
H6	0.5781	−0.0720	0.1014	0.068*
C7	0.399 (3)	0.0198 (10)	0.0433 (4)	0.055 (3)
H7	0.3336	−0.0393	0.0228	0.066*
C8	0.367 (2)	0.1372 (9)	0.0325 (3)	0.040 (2)
C9	0.224 (2)	0.1930 (9)	−0.0097 (4)	0.047 (2)
C10	0.115 (2)	0.1212 (13)	−0.0502 (3)	0.056 (2)
H10	0.1262	0.0410	−0.0477	0.067*
C11	0.004 (3)	0.1676 (9)	−0.0897 (3)	0.050 (3)
H11	−0.0011	0.2481	−0.0904	0.060*
C12	−0.1123 (19)	0.1090 (13)	−0.1328 (3)	0.047 (2)
C13	−0.161 (2)	0.1657 (10)	−0.1751 (4)	0.056 (3)
C14	−0.284 (2)	0.1127 (16)	−0.2156 (3)	0.059 (2)
H14	−0.3209	0.1551	−0.2433	0.071*
C15	−0.351 (3)	−0.0028 (14)	−0.2143 (4)	0.071 (3)
H15	−0.4279	−0.0402	−0.2415	0.085*
C16	−0.305 (3)	−0.0644 (12)	−0.1730 (4)	0.070 (3)
H16	−0.3591	−0.1428	−0.1723	0.084*
C17	−0.179 (3)	−0.0115 (10)	−0.1326 (4)	0.065 (3)
H17	−0.1375	−0.0550	−0.1053	0.077*

	U11	U22	U33	U12	U13	U23
Br1	0.0533 (5)	0.0886 (8)	0.0426 (5)	0.0105 (8)	−0.0063 (4)	−0.0005 (9)
S2	0.0619 (19)	0.0474 (14)	0.0454 (14)	0.0001 (14)	−0.0050 (14)	−0.0022 (12)
Cl2	0.114 (3)	0.0636 (19)	0.0588 (18)	−0.0100 (19)	−0.0207 (17)	0.0143 (15)
O4	0.105 (6)	0.045 (5)	0.067 (5)	−0.003 (4)	−0.014 (4)	0.005 (4)
C5	0.043 (4)	0.049 (6)	0.043 (4)	0.002 (6)	0.003 (3)	0.003 (5)
C6	0.060 (7)	0.050 (7)	0.060 (7)	0.013 (6)	−0.009 (6)	0.012 (5)
C7	0.063 (7)	0.040 (6)	0.063 (7)	0.004 (5)	−0.004 (5)	−0.002 (5)
C8	0.038 (5)	0.046 (7)	0.036 (4)	0.002 (4)	0.001 (3)	0.008 (4)
C9	0.039 (6)	0.049 (7)	0.054 (6)	−0.006 (4)	−0.002 (4)	0.004 (5)
C10	0.056 (5)	0.059 (6)	0.053 (5)	0.006 (7)	−0.005 (4)	−0.010 (7)
C11	0.059 (7)	0.048 (5)	0.043 (5)	−0.016 (4)	−0.012 (5)	0.005 (4)
C12	0.037 (4)	0.063 (6)	0.041 (4)	0.001 (7)	0.004 (3)	−0.002 (6)
C13	0.042 (5)	0.065 (7)	0.062 (7)	0.005 (5)	0.012 (5)	0.005 (5)
C14	0.063 (6)	0.075 (7)	0.039 (4)	0.006 (8)	−0.009 (4)	−0.004 (9)
C15	0.069 (8)	0.110 (11)	0.034 (6)	0.007 (7)	0.002 (5)	−0.012 (6)
C16	0.074 (8)	0.059 (8)	0.077 (9)	−0.015 (6)	0.002 (7)	−0.023 (7)
C17	0.073 (7)	0.055 (7)	0.066 (7)	−0.007 (6)	−0.004 (6)	0.010 (6)

Br1—C5	1.880 (9)	C10—H10	0.9300
S2—C5	1.691 (11)	C11—C12	1.462 (13)
S2—C8	1.697 (10)	C11—H11	0.9300
Cl2—C13	1.750 (12)	C12—C13	1.370 (14)
O4—C9	1.230 (12)	C12—C17	1.417 (19)
C5—C6	1.329 (16)	C13—C14	1.382 (15)
C6—C7	1.397 (14)	C14—C15	1.36 (3)
C6—H6	0.9300	C14—H14	0.9300
C7—C8	1.395 (16)	C15—C16	1.374 (17)
C7—H7	0.9300	C15—H15	0.9300
C8—C9	1.462 (13)	C16—C17	1.381 (16)
C9—C10	1.473 (15)	C16—H16	0.9300
C10—C11	1.306 (13)	C17—H17	0.9300
C5—S2—C8	90.9 (5)	C10—C11—H11	115.9
C6—C5—S2	114.6 (7)	C12—C11—H11	115.9
C6—C5—Br1	125.4 (9)	C13—C12—C17	116.6 (10)
S2—C5—Br1	120.0 (7)	C13—C12—C11	122.8 (12)
C5—C6—C7	111.2 (10)	C17—C12—C11	120.6 (10)
C5—C6—H6	124.4	C12—C13—C14	123.5 (13)
C7—C6—H6	124.4	C12—C13—Cl2	119.8 (10)
C8—C7—C6	112.7 (10)	C14—C13—Cl2	116.7 (10)
C8—C7—H7	123.7	C15—C14—C13	118.7 (11)
C6—C7—H7	123.7	C15—C14—H14	120.7
C7—C8—C9	129.7 (9)	C13—C14—H14	120.7
C7—C8—S2	110.7 (7)	C14—C15—C16	120.4 (10)
C9—C8—S2	119.6 (8)	C14—C15—H15	119.8
O4—C9—C8	118.4 (10)	C16—C15—H15	119.8
O4—C9—C10	122.2 (10)	C15—C16—C17	120.8 (12)
C8—C9—C10	119.5 (10)	C15—C16—H16	119.6
C11—C10—C9	121.5 (13)	C17—C16—H16	119.6
C11—C10—H10	119.2	C16—C17—C12	119.8 (11)
C9—C10—H10	119.2	C16—C17—H17	120.1
C10—C11—C12	128.2 (12)	C12—C17—H17	120.1
C8—S2—C5—C6	−0.3 (8)	C9—C10—C11—C12	−179.9 (9)
C8—S2—C5—Br1	−178.3 (5)	C10—C11—C12—C13	−166.9 (10)
S2—C5—C6—C7	0.8 (12)	C10—C11—C12—C17	12.5 (16)
Br1—C5—C6—C7	178.7 (7)	C17—C12—C13—C14	3.3 (14)
C5—C6—C7—C8	−1.1 (14)	C11—C12—C13—C14	−177.3 (9)
C6—C7—C8—C9	−178.2 (10)	C17—C12—C13—Cl2	−177.6 (8)
C6—C7—C8—S2	0.9 (12)	C11—C12—C13—Cl2	1.9 (13)
C5—S2—C8—C7	−0.4 (8)	C12—C13—C14—C15	−2.4 (15)
C5—S2—C8—C9	178.8 (8)	Cl2—C13—C14—C15	178.5 (8)
C7—C8—C9—O4	175.0 (10)	C13—C14—C15—C16	1.8 (17)
S2—C8—C9—O4	−4.0 (13)	C14—C15—C16—C17	−2.3 (19)
C7—C8—C9—C10	−5.4 (16)	C15—C16—C17—C12	3.3 (18)
S2—C8—C9—C10	175.6 (7)	C13—C12—C17—C16	−3.7 (15)
O4—C9—C10—C11	3.5 (16)	C11—C12—C17—C16	176.8 (10)
C8—C9—C10—C11	−176.1 (9)