Crystal structure of (2E)-1-(5-bromo­thio­phen-2-yl)-3-(2-chloro­phen­yl)prop-2-en-1-one

Anitha, B.R.; Vinduvahini, M.; Ravi, A.J.; Devarajegowda, H.C.

doi:10.1107/S2056989015021155

organic compounds

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Volume 71| Part 12| December 2015| Page o930

https://doi.org/10.1107/S2056989015021155

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Crystal structure of (2E)-1-(5-bromothiophen-2-yl)-3-(2-chlorophenyl)prop-2-en-1-one

B. R. Anitha,^a M. Vinduvahini,^b A. J. Ravi ^a and H. C. Devarajegowda ^a ^*

^aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, and ^bDepartment of Physics, Sri D Devaraja Urs Govt. First Grade College, Hunsur 571 105, Mysore District, Karnataka, India
^*Correspondence e-mail: devarajegowda@yahoo.com

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 7 November 2015; accepted 7 November 2015; online 14 November 2015)

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, molecules stack along the a axis, with the interplanar separation between thienyl rings and between benzene rings being 3.925 (6) Å. The sample is an inversion twin.

Keywords: crystal structure; chalcone; π–π interactions.

CCDC reference: 1435865

1. 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 ).

2. Experimental

2.1. Crystal data

C₁₃H₈BrClOS
M_r = 327.61
Orthorhombic, P c 2₁ b
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.137
S = 1.10
3007 reflections
155 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.79 e Å⁻³
Δρ_min = −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.

Supporting information

CCDC reference: 1435865

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989015021155/tk5406sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015021155/tk5406Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015021155/tk5406Isup3.cml

checkCIF report

Comment top

Chalcones are alpha,beta unsaturated ketones, widely distributed in nature and are extensively studied for their biological activity (Lin et al., 2001; Horng et al., 2003; López et al., 2001; Liu 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 asymmetric unit of (2E)-1-(5-bromo-2-thienyl)-3-(2-chlorophenyl) prop-2-en-1-one, C₁₃H₈Br Cl O S, contains just one molecule (Fig. 1). The five-membered thiophene ring (S2,C5–C8) is not coplanar with the benzene ring (C12–C17); the dihedral angle between the two planes is 13.2 (4)°. Bond lengths and angles are in good agreement with those observed in related crystal structures (Liang et al., 2011; Alex et al., 1993; Li et al., 1993).

Related literature top

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 top

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

Structure description top

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).

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: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Figures top

Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level.

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

Crystal data top

C₁₃H₈BrClOS	D_x = 1.708 Mg m⁻³
M_r = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0565P)² + 0.585P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.137	(Δ/σ)_max < 0.001
S = 1.10	Δρ_max = 0.79 e Å⁻³
3007 reflections	Δρ_min = −0.33 e Å⁻³
155 parameters	Absolute structure: refined as an inversion twin
1 restraint	Absolute structure parameter: 0.15 (3)

Crystal data top

C₁₃H₈BrClOS	V = 1274.1 (11) Å³
M_r = 327.61	Z = 4
Orthorhombic, Pc2₁b	Mo Kα radiation
a = 3.9247 (19) Å	µ = 3.58 mm⁻¹
b = 11.549 (6) Å	T = 293 K
c = 28.111 (14) Å	0.24 × 0.20 × 0.12 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3007 independent reflections
Absorption correction: ψ scan (SADABS; Sheldrick, 2007)	2096 reflections with I > 2σ(I)
T_min = 0.770, T_max = 1.000	R_int = 0.065
12995 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	H-atom parameters constrained
wR(F²) = 0.137	Δρ_max = 0.79 e Å⁻³
S = 1.10	Δρ_min = −0.33 e Å⁻³
3007 reflections	Absolute structure: refined as an inversion twin
155 parameters	Absolute structure parameter: 0.15 (3)
1 restraint

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₃H₈BrClOS
M_r	327.61
Crystal system, space group	Orthorhombic, Pc2₁b
Temperature (K)	293
a, b, c (Å)	3.9247 (19), 11.549 (6), 28.111 (14)
V (Å³)	1274.1 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.58
Crystal size (mm)	0.24 × 0.20 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	ψ scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.770, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12995, 3007, 2096
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.137, 1.10
No. of reflections	3007
No. of parameters	155
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.79, −0.33
Absolute structure	Refined as an inversion twin
Absolute structure parameter	0.15 (3)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), ORTEP-3 for Windows (Farrugia, 2012).

Acknowledgements

The authors thank Professor T. N. Guru Row, SSCU, IISc, Bangalore, for support in the X-ray data collection.

References

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