(2E)-1-(5-Bromothiophen-2-yl)-3-(4-chloro­phen­yl)prop-2-en-1-one

Kavitha, H.D.; Roopashree, K.R.; Vepuri, S.B.; Devarajegowda, H.C.; Devaru, V.B.

doi:10.1107/S1600536813012063

organic compounds

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doi:10.1107/S1600536813012063

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(2E)-1-(5-Bromothiophen-2-yl)-3-(4-chlorophenyl)prop-2-en-1-one

H. D. Kavitha,^a K. R. Roopashree,^b Suresh B. Vepuri,^c H. C. Devarajegowda ^b ^* and Venkatesh B. Devaru ^d

^aDepartment of Physics, Govt. Science College, Hassan 573 201, Karnataka, India, ^bDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570005, Karnataka, India, ^cInstitute of Pharmacy, GITAM University, Visakhapatnam-45, Andhrapradesh, India, and ^dDepartment of Physics, P. G. Department of Physics, LVD College, Raichur 584103, Karnataka, India
^*Correspondence e-mail: devarajegowda@yahoo.com

(Received 9 April 2013; accepted 3 May 2013; online 11 May 2013)

In the title compound, C₁₃H₈BrClOS, the thiophene and phenyl rings are inclined by 40.69 (11)° to each other. The crystal structure is characterized by C—H⋯π interactions, which link the molecules into broad layers parallel to (100). Short Br⋯Cl contacts [3.698 (1) Å] link these layers along [100].

Related literature

For general background to chalcones, see: Chun et al. (2001 ); Horng et al. (2003 ); Lopez et al. (2001 ); Mei et al. (2003 ). For related structures, see: Vepuri et al. (2012 ); Li & Su (1993 ).

Experimental

Crystal data

C₁₃H₈BrClOS
M_r = 327.61
Monoclinic, P 2₁ /c
a = 15.235 (3) Å
b = 13.959 (3) Å
c = 5.9153 (11) Å
β = 93.259 (3)°
V = 1255.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 3.63 mm⁻¹
T = 293 K
0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.770, T_max = 1.000
14247 measured reflections
3032 independent reflections
2204 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.081
S = 1.05
3032 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯Cg2ⁱ	0.93	2.87	3.557 (3)	132
C16—H16⋯Cg2ⁱⁱ	0.93	2.96	3.480 (3)	117
Symmetry codes: (i) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z+2.

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: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813012063/bg2505sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813012063/bg2505Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813012063/bg2505Isup3.cml

checkCIF report

Comment top

Chalcones are alpha beta unsaturated ketones, widely distributed in nature and are extensively studied for their biological activity (Chun et al., 2001; Horng et al., 2003; Lopez et al., 2001; Mei et al., 2003). We report here the crystal structure of a bromo derivative of hetero aryl chalcone which has shown aldose reductase inhibition in the virtual screening study conducted by us.

The titlecompound (2E)-1-(5-bromo-2-thienyl)-3-(4- chlorophenyl)prop-2-en-1-one, C₁₃H₈Br Cl O S, presents a five-membered thiophene ring (S3\C14\···C17) and a phenyl ring (C5\C6\···C10) at 40.69 (11)° to each other (Fig 1). All intermolecular bond lengths and angles are within normal ranges (Vepuri et al., 2012; Li & Su, 1993). The crystal structure is characterized by C—H···π interactions (C10—H10···Cg2; C16—H16···Cg2, Cg2 = C5->C10) (Table 1) which link molecules into broad 2D structures parallel to (100). There are in addition short intermolecular Br1···Cl2 contacts of 3.698 (1) Å, which link these structures along [100]. (Fig 2)

Related literature top

For general background to chalcones, see: Chun et al. (2001); Horng et al. (2003); Lopez et al. (2001); Mei et al. (2003). For related structures, see: Vepuri et al. (2012); Li & Su (1993).

Experimental top

A mixture of 2-acetyl-5-BromoThiophene (0.01 mole) and 4-chlorobenzaldehyde (0.01 mole) were stirred in ethanol (30 ml) and then an aqueous solution of potassium hydroxide (40%,15 ml)was added to it. The mixture was kept over night at room temperature and then it was poured into crushed ice and acidified with dilute hydrochloric acid. The precipiteted chalcone was filtered and crystallized from ethanol.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing of the title compound. Dashed lines represent C-H···π and Br···Cl bonds.

(2E)-1-(5-Bromothiophen-2-yl)-3-(4-chlorophenyl)prop-2-en-1-one top

Crystal data top

C₁₃H₈BrClOS	F(000) = 648
M_r = 327.61	D_x = 1.733 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 399 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.235 (3) Å	Cell parameters from 2202 reflections
b = 13.959 (3) Å	θ = 2.0–25.0°
c = 5.9153 (11) Å	µ = 3.63 mm⁻¹
β = 93.259 (3)°	T = 293 K
V = 1255.9 (4) Å³	Plate, colourless
Z = 4	0.24 × 0.20 × 0.12 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3032 independent reflections
Radiation source: fine-focus sealed tube	2204 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω and ϕ scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −18→18
T_min = 0.770, T_max = 1.000	k = 0→16
14247 measured reflections	l = 0→7

Refinement top

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.081	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0473P)² + 0.2986P] where P = (F_o² + 2F_c²)/3
2202 reflections	(Δ/σ)_max = 0.001
154 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₃H₈BrClOS	V = 1255.9 (4) Å³
M_r = 327.61	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.235 (3) Å	µ = 3.63 mm⁻¹
b = 13.959 (3) Å	T = 293 K
c = 5.9153 (11) Å	0.24 × 0.20 × 0.12 mm
β = 93.259 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3032 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2204 reflections with I > 2σ(I)
T_min = 0.770, T_max = 1.000	R_int = 0.023
14247 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.081	H-atom parameters constrained
S = 1.05	Δρ_max = 0.40 e Å⁻³
2202 reflections	Δρ_min = −0.29 e Å⁻³
154 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.876810 (18)	0.34860 (2)	0.10591 (6)	0.06662 (15)
Cl2	0.03637 (5)	0.36156 (7)	0.68667 (14)	0.0719 (3)
S3	0.67904 (4)	0.34879 (5)	−0.04338 (10)	0.04481 (18)
O4	0.48985 (13)	0.37196 (16)	−0.1517 (3)	0.0642 (6)
C5	0.13007 (16)	0.37433 (18)	0.5358 (4)	0.0436 (6)
C6	0.12401 (15)	0.41523 (19)	0.3238 (4)	0.0466 (6)
H6	0.0705	0.4381	0.2626	0.056*
C7	0.19854 (15)	0.42171 (17)	0.2044 (4)	0.0421 (6)
H7	0.1943	0.4480	0.0598	0.051*
C8	0.28016 (15)	0.39015 (16)	0.2928 (4)	0.0369 (5)
C9	0.28356 (16)	0.35027 (16)	0.5098 (4)	0.0407 (6)
H9	0.3372	0.3292	0.5743	0.049*
C10	0.20961 (17)	0.34157 (16)	0.6295 (4)	0.0431 (6)
H10	0.2129	0.3138	0.7727	0.052*
C11	0.35582 (15)	0.39464 (17)	0.1545 (4)	0.0399 (5)
H11	0.3445	0.4112	0.0034	0.048*
C12	0.43893 (16)	0.37794 (19)	0.2184 (4)	0.0450 (6)
H12	0.4544	0.3669	0.3706	0.054*
C13	0.50768 (17)	0.37658 (18)	0.0522 (4)	0.0431 (6)
C14	0.59921 (15)	0.37793 (16)	0.1398 (4)	0.0371 (5)
C15	0.63572 (16)	0.40178 (19)	0.3477 (4)	0.0454 (6)
H15	0.6027	0.4194	0.4684	0.055*
C16	0.72770 (16)	0.39728 (19)	0.3626 (4)	0.0464 (6)
H16	0.7625	0.4121	0.4922	0.056*
C17	0.75950 (15)	0.36879 (17)	0.1654 (4)	0.0410 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03415 (18)	0.0911 (3)	0.0755 (2)	0.00978 (13)	0.01087 (14)	0.00945 (16)
Cl2	0.0432 (4)	0.1058 (7)	0.0687 (5)	−0.0075 (4)	0.0196 (3)	0.0045 (4)
S3	0.0374 (4)	0.0601 (4)	0.0373 (3)	0.0041 (3)	0.0062 (3)	−0.0034 (3)
O4	0.0443 (11)	0.1042 (17)	0.0438 (11)	0.0027 (10)	−0.0004 (8)	−0.0067 (10)
C5	0.0348 (13)	0.0501 (14)	0.0466 (14)	−0.0074 (11)	0.0069 (11)	−0.0050 (12)
C6	0.0318 (13)	0.0592 (17)	0.0483 (15)	0.0033 (11)	−0.0024 (10)	0.0017 (12)
C7	0.0377 (13)	0.0474 (14)	0.0407 (13)	0.0003 (11)	−0.0025 (10)	0.0034 (11)
C8	0.0344 (12)	0.0350 (12)	0.0411 (13)	−0.0037 (10)	0.0003 (10)	−0.0021 (10)
C9	0.0351 (13)	0.0433 (14)	0.0431 (14)	0.0022 (10)	−0.0029 (11)	−0.0003 (10)
C10	0.0452 (14)	0.0432 (14)	0.0408 (14)	−0.0018 (11)	0.0013 (11)	0.0006 (10)
C11	0.0367 (13)	0.0429 (13)	0.0400 (13)	−0.0018 (10)	0.0020 (10)	−0.0024 (10)
C12	0.0369 (14)	0.0580 (15)	0.0402 (13)	0.0007 (11)	0.0039 (11)	0.0015 (11)
C13	0.0367 (13)	0.0484 (14)	0.0441 (15)	0.0010 (11)	0.0017 (11)	0.0003 (11)
C14	0.0320 (12)	0.0393 (13)	0.0406 (13)	0.0014 (10)	0.0077 (10)	−0.0008 (10)
C15	0.0424 (14)	0.0525 (16)	0.0420 (14)	0.0038 (11)	0.0077 (11)	−0.0078 (11)
C16	0.0407 (14)	0.0555 (16)	0.0430 (14)	−0.0036 (12)	0.0004 (11)	−0.0066 (12)
C17	0.0300 (12)	0.0426 (13)	0.0507 (14)	−0.0018 (10)	0.0042 (10)	0.0034 (11)

Geometric parameters (Å, º) top

Br1—C17	1.863 (2)	C9—C10	1.370 (3)
Cl2—C5	1.735 (3)	C9—H9	0.9300
S3—C17	1.713 (3)	C10—H10	0.9300
S3—C14	1.723 (2)	C11—C12	1.321 (3)
O4—C13	1.223 (3)	C11—H11	0.9300
C5—C6	1.376 (4)	C12—C13	1.477 (3)
C5—C10	1.381 (4)	C12—H12	0.9300
C6—C7	1.374 (3)	C13—C14	1.460 (3)
C6—H6	0.9300	C14—C15	1.362 (3)
C7—C8	1.393 (3)	C15—C16	1.400 (3)
C7—H7	0.9300	C15—H15	0.9300
C8—C9	1.397 (3)	C16—C17	1.348 (3)
C8—C11	1.452 (3)	C16—H16	0.9300

C17—S3—C14	90.57 (12)	C12—C11—H11	116.2
C6—C5—C10	121.0 (2)	C8—C11—H11	116.2
C6—C5—Cl2	119.8 (2)	C11—C12—C13	121.1 (2)
C10—C5—Cl2	119.2 (2)	C11—C12—H12	119.5
C7—C6—C5	118.8 (2)	C13—C12—H12	119.5
C7—C6—H6	120.6	O4—C13—C14	120.3 (2)
C5—C6—H6	120.6	O4—C13—C12	122.1 (2)
C6—C7—C8	122.2 (2)	C14—C13—C12	117.6 (2)
C6—C7—H7	118.9	C15—C14—C13	131.0 (2)
C8—C7—H7	118.9	C15—C14—S3	111.04 (18)
C7—C8—C9	117.2 (2)	C13—C14—S3	117.92 (18)
C7—C8—C11	119.7 (2)	C14—C15—C16	113.7 (2)
C9—C8—C11	123.1 (2)	C14—C15—H15	123.2
C10—C9—C8	121.4 (2)	C16—C15—H15	123.2
C10—C9—H9	119.3	C17—C16—C15	111.5 (2)
C8—C9—H9	119.3	C17—C16—H16	124.3
C9—C10—C5	119.4 (2)	C15—C16—H16	124.3
C9—C10—H10	120.3	C16—C17—S3	113.23 (19)
C5—C10—H10	120.3	C16—C17—Br1	127.2 (2)
C12—C11—C8	127.6 (2)	S3—C17—Br1	119.61 (14)

C10—C5—C6—C7	1.0 (4)	C11—C12—C13—C14	167.3 (2)
Cl2—C5—C6—C7	−177.9 (2)	O4—C13—C14—C15	164.8 (3)
C5—C6—C7—C8	−1.4 (4)	C12—C13—C14—C15	−17.0 (4)
C6—C7—C8—C9	0.6 (4)	O4—C13—C14—S3	−12.8 (3)
C6—C7—C8—C11	177.1 (2)	C12—C13—C14—S3	165.31 (18)
C7—C8—C9—C10	0.7 (3)	C17—S3—C14—C15	0.3 (2)
C11—C8—C9—C10	−175.7 (2)	C17—S3—C14—C13	178.47 (19)
C8—C9—C10—C5	−1.1 (4)	C13—C14—C15—C16	−177.6 (2)
C6—C5—C10—C9	0.2 (4)	S3—C14—C15—C16	0.2 (3)
Cl2—C5—C10—C9	179.09 (18)	C14—C15—C16—C17	−0.8 (3)
C7—C8—C11—C12	171.9 (3)	C15—C16—C17—S3	1.0 (3)
C9—C8—C11—C12	−11.8 (4)	C15—C16—C17—Br1	−177.94 (19)
C8—C11—C12—C13	174.2 (2)	C14—S3—C17—C16	−0.8 (2)
C11—C12—C13—O4	−14.5 (4)	C14—S3—C17—Br1	178.26 (15)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C5–C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cg2ⁱ	0.93	2.87	3.557 (3)	132
C16—H16···Cg2ⁱⁱ	0.93	2.96	3.480 (3)	117

Symmetry codes: (i) x, −y−1/2, z−1/2; (ii) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₃H₈BrClOS
M_r	327.61
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	15.235 (3), 13.959 (3), 5.9153 (11)
β (°)	93.259 (3)
V (Å³)	1255.9 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.63
Crystal size (mm)	0.24 × 0.20 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.770, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	14247, 3032, 2204
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.081, 1.05
No. of reflections	2202
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.29

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C5–C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cg2ⁱ	0.93	2.87	3.557 (3)	132
C16—H16···Cg2ⁱⁱ	0.93	2.96	3.480 (3)	117

Symmetry codes: (i) x, −y−1/2, z−1/2; (ii) −x+1, −y, −z+2.

Acknowledgements

The authors thank Professor T. N. Guru Row, Soild State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for his constant support and for the data collection.

References

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