(2E)-3-(1,3-Benzodioxol-5-yl)-1-(3-bromo-2-thien­yl)prop-2-en-1-one

Harrison, W.T.A.; Chidan Kumar, C.S.; Yathirajan, H.S.; Ashalatha, B.V.; Narayana, B.

doi:10.1107/S1600536810035129

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2477

doi:10.1107/S1600536810035129

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(2E)-3-(1,3-Benzodioxol-5-yl)-1-(3-bromo-2-thienyl)prop-2-en-1-one

William T. A. Harrison,^a ^* C. S. Chidan Kumar,^b H. S. Yathirajan,^b B. V. Ashalatha ^c and B. Narayana ^c

^aDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland, ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^cDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, India
^*Correspondence e-mail: w.harrison@abdn.ac.uk

(Received 10 August 2010; accepted 31 August 2010; online 4 September 2010)

In the title molecule, C₁₄H₉BrO₃S, the the prop-2-en-1-one (enone) fragment is close to planar [C—C—C—O = 2.5 (7)°] and it subtends dihedral angles of 12.5 (3) and 5.3 (4)° with respect to the thiophene and benzene rings, respectively. The dihedral angle between the aromatic ring systems is 12.60 (18)°. Two C—H⋯O interactions help to consolidate the non-centrosymmetic crystal packing, which features undulating (100) sheets incorporating C(11) and C(12) chain motifs.

Related literature

For related structures, see: Butcher et al. (2007 ); Harrison et al. (2006 , 2007 ); Yathirajan et al. (2006a ,b ,c ). For background to chalcone derivatives as non-linear optical materials, see: Sarojini et al. (2006 ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₉BrO₃S
M_r = 337.18
Monoclinic, P 2₁
a = 4.0013 (3) Å
b = 11.0211 (9) Å
c = 14.6931 (11) Å
β = 95.781 (2)°
V = 644.65 (9) Å³
Z = 2
Mo Kα radiation
μ = 3.35 mm⁻¹
T = 291 K
0.48 × 0.16 × 0.09 mm

Data collection

Bruker SMART1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.296, T_max = 0.753
4452 measured reflections
2684 independent reflections
2180 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.091
S = 0.94
2684 reflections
172 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.43 e Å⁻³
Absolute structure: Flack (1983 ), 1127 Friedel pairs
Flack parameter: 0.057 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O2ⁱ	0.93	2.51	3.420 (6)	167
C14—H14A⋯O1ⁱⁱ	0.97	2.44	3.400 (6)	171
Symmetry codes: (i) x, y, z+1; (ii) $[-x+1, y-{\script{1\over 2}}, -z+1]$ .

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); 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 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035129/su2204sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810035129/su2204Isup2.hkl

checkCIF report

Comment top

The title compound (Fig. 1), was prepared as part of our ongoing synthetic and structural studies of molecules containing thienyl and aromatic rings linked by an enone bridge as possible non-linear optical materials (Sarojini et al., 2006). The crystal structures of (2E)-1-(3-bromo-2-thienyl)-3-(4,5-dimethoxy-2-nitrophenyl)prop-2-en-1-one (Yathirajan et al., 2006a), (2E)-1-(3-bromo-2-thienyl)-3-(2,5-dimethoxyphenyl)prop-2-en-1-one (Yathirajan et al., 2006b), (2E)-1-(3-bromo-2-thienyl)-3-(4-methoxy-2,3,6-trimethylphenyl)prop-2-en-1-one (Yathirajan et al., 2006c), (2E)-1-(3-bromo-2-thienyl)-3-(4-methoxyphenyl)prop-2-en-1-one (Harrison et al., 2006), 1-(3-bromo-2-thienyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one (Butcher et al., 2007), (2E)-1-(3-bromo-2-thienyl)-3-(4-nitrophenyl)prop-2-en-1-one (Harrison et al., 2007) have been reported previously.

The C4—C3—Br1 angle in the title molecule of 127.0 (3)° is significantly larger than angle C2—C3—Br1 [118.3 (3)°], perhaps due to steric repulsion between atoms Br1 and H6 (H···Br = 2.75 Å), as also seen in a related structure (Harrison et al., 2007). Br1 is displaced from the C1—C4/S1 ring mean plane by 0.047 (6) Å.

The enone fragment is close to planar [O1—C5—C6—C7 = 2.5 (7)°] and it subtends dihedral angles of 12.5 (3)° and 5.3 (4)°, respectively, with respect to the adjacent thienyl (C1—C4/S1) and benzene (C8—C13) rings. The O and S atoms are in a syn conformation [S1—C4—C5—O1 = 11.0 (5)°]. The dihedral angle between the thienyl and benzene ring systems is 12.60 (18)°. The five-membered C11/C12/C14/O2/O3 ring is almost planar (r.m.s. deviation = 0.003 Å) and it subtends a dihedral angle of 0.6 (3)° with ring C8–C13, i.e. the rings are statistically co-planar.

In the crystal of the title compound, two weak C—H···O interactions occur (Table 1). The bond involving atom H1 leads to C(12) chains propagating in [001], and that involving atom H14A to zigzag C(11) chains in [010]. Taken together, (100) sheets (Fig. 2) arise, in which unusual R⁴₄(31) loops are apparent.

Related literature top

For related structures, see: Butcher et al. (2007); Harrison et al. (2006, 2007); Yathirajan et al. (2006a,b,c). For background to chalcone derivatives as non-linear optical materials, see: Sarojini et al. (2006). For reference structural data, see: Allen et al. (1987).

Experimental top

To 1-(3-Bromo-2-thienyl)ethanone (2.0 g, 0.01 mol) and 1,3-benzodioxole-5-carbaldehyde (1.5 g, 0.01 mol) in 25 ml of methanol, 5 ml of 10% KOH solution was slowly added with stirring at 278 K, and the stirring was continued for 4 h at RT. The solid separated was filtered out and washed with cold methanol. Recrystallization from methanol yielded the pure compound in 90% yield. Pale yellow bar-like crystals of the title compound were obtained by slow evaporation of a solution in acetone (m.p.: 419–421 K).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. View of the molecular structure of the title molecule showing 50% displacement ellipsoids (arbitrary spheres for the H atoms).
	Fig. 2. View approximately down [100] of part of a (100) sheet in the crystal structure of the title compound, with C—H···O interactions indicated by double-dashed lines [Symmetry codes: (i) x, y, z + 1; (ii) 1–x, y–1/2, 1–z].

(2E)-3-(1,3-Benzodioxol-5-yl)-1-(3-bromo-2-thienyl)prop-2-en-1-one top

Crystal data top

C₁₄H₉BrO₃S	F(000) = 336
M_r = 337.18	D_x = 1.737 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2038 reflections
a = 4.0013 (3) Å	θ = 2.3–26.0°
b = 11.0211 (9) Å	µ = 3.35 mm⁻¹
c = 14.6931 (11) Å	T = 291 K
β = 95.781 (2)°	Bar, pale yellow
V = 644.65 (9) Å³	0.48 × 0.16 × 0.09 mm
Z = 2

Data collection top

Bruker SMART1000 CCD diffractometer	2684 independent reflections
Radiation source: fine-focus sealed tube	2180 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −5→5
T_min = 0.296, T_max = 0.753	k = −14→13
4452 measured reflections	l = −14→19

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0549P)²] where P = (F_o² + 2F_c²)/3
S = 0.94	(Δ/σ)_max < 0.001
2684 reflections	Δρ_max = 0.48 e Å⁻³
172 parameters	Δρ_min = −0.43 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1127 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.057 (11)

Crystal data top

C₁₄H₉BrO₃S	V = 644.65 (9) Å³
M_r = 337.18	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 4.0013 (3) Å	µ = 3.35 mm⁻¹
b = 11.0211 (9) Å	T = 291 K
c = 14.6931 (11) Å	0.48 × 0.16 × 0.09 mm
β = 95.781 (2)°

Data collection top

Bruker SMART1000 CCD diffractometer	2684 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	2180 reflections with I > 2σ(I)
T_min = 0.296, T_max = 0.753	R_int = 0.032
4452 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.091	Δρ_max = 0.48 e Å⁻³
S = 0.94	Δρ_min = −0.43 e Å⁻³
2684 reflections	Absolute structure: Flack (1983), 1127 Friedel pairs
172 parameters	Absolute structure parameter: 0.057 (11)
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. 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.

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

	x	y	z	U_iso*/U_eq
C1	0.2722 (13)	0.4301 (5)	1.0496 (3)	0.0542 (12)
H1	0.2566	0.4347	1.1122	0.065*
C2	0.1769 (12)	0.3322 (4)	0.9984 (3)	0.0454 (10)
H2	0.0956	0.2606	1.0216	0.054*
C3	0.2158 (10)	0.3519 (4)	0.9061 (3)	0.0382 (9)
C4	0.3482 (10)	0.4619 (4)	0.8875 (3)	0.0372 (9)
C5	0.4449 (11)	0.5265 (4)	0.8055 (3)	0.0417 (9)
C6	0.3357 (11)	0.4825 (4)	0.7134 (3)	0.0448 (10)
H6	0.2024	0.4134	0.7060	0.054*
C7	0.4251 (10)	0.5406 (4)	0.6393 (3)	0.0420 (9)
H7	0.5671	0.6067	0.6512	0.050*
C8	0.3315 (10)	0.5148 (4)	0.5429 (3)	0.0375 (9)
C9	0.4268 (11)	0.5987 (4)	0.4795 (3)	0.0451 (10)
H9	0.5445	0.6676	0.5007	0.054*
C10	0.3519 (12)	0.5833 (4)	0.3846 (3)	0.0472 (11)
H10	0.4155	0.6394	0.3424	0.057*
C11	0.1795 (11)	0.4802 (4)	0.3591 (3)	0.0419 (10)
C12	0.0810 (11)	0.3961 (4)	0.4208 (3)	0.0409 (9)
C13	0.1519 (11)	0.4098 (4)	0.5127 (3)	0.0426 (10)
H13	0.0850	0.3526	0.5538	0.051*
C14	−0.0909 (13)	0.3301 (5)	0.2780 (3)	0.0560 (12)
H14A	0.0216	0.2669	0.2467	0.067*
H14B	−0.3212	0.3360	0.2506	0.067*
O1	0.6119 (9)	0.6200 (3)	0.8178 (2)	0.0626 (10)
O2	0.0773 (10)	0.4431 (3)	0.2707 (2)	0.0610 (9)
O3	−0.0837 (11)	0.3020 (3)	0.3741 (2)	0.0673 (10)
S1	0.4233 (3)	0.54359 (10)	0.98785 (7)	0.0466 (3)
Br1	0.10081 (12)	0.22426 (4)	0.82175 (3)	0.05698 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.075 (3)	0.052 (3)	0.036 (2)	0.008 (2)	0.010 (2)	0.003 (2)
C2	0.053 (3)	0.038 (2)	0.046 (2)	0.001 (2)	0.013 (2)	0.0039 (18)
C3	0.039 (2)	0.034 (2)	0.041 (2)	0.0020 (17)	0.0000 (17)	0.0001 (17)
C4	0.037 (2)	0.034 (2)	0.039 (2)	0.0027 (17)	−0.0029 (17)	0.0007 (16)
C5	0.044 (2)	0.042 (3)	0.039 (2)	0.0031 (19)	0.0028 (17)	0.0072 (18)
C6	0.051 (2)	0.041 (3)	0.042 (2)	−0.002 (2)	0.0050 (18)	0.0025 (19)
C7	0.045 (2)	0.038 (2)	0.044 (2)	0.0024 (19)	0.0048 (18)	0.0061 (19)
C8	0.043 (2)	0.035 (2)	0.035 (2)	0.0075 (17)	0.0028 (17)	0.0020 (16)
C9	0.054 (3)	0.036 (2)	0.046 (2)	−0.0042 (19)	0.006 (2)	0.0061 (18)
C10	0.057 (3)	0.043 (3)	0.043 (2)	−0.003 (2)	0.011 (2)	0.0155 (19)
C11	0.045 (2)	0.048 (3)	0.033 (2)	0.008 (2)	0.0071 (17)	−0.0012 (18)
C12	0.048 (2)	0.031 (2)	0.045 (2)	0.0013 (18)	0.0104 (18)	−0.0029 (17)
C13	0.051 (3)	0.036 (2)	0.043 (2)	0.0033 (19)	0.0157 (19)	0.0091 (18)
C14	0.063 (3)	0.057 (3)	0.048 (3)	0.004 (2)	0.004 (2)	−0.010 (2)
O1	0.084 (3)	0.047 (2)	0.055 (2)	−0.0276 (18)	−0.0008 (18)	0.0074 (16)
O2	0.088 (3)	0.058 (2)	0.0364 (17)	−0.0052 (19)	0.0062 (16)	0.0002 (15)
O3	0.104 (3)	0.047 (2)	0.051 (2)	−0.019 (2)	0.0081 (19)	−0.0067 (16)
S1	0.0637 (7)	0.0337 (6)	0.0415 (6)	−0.0011 (5)	0.0013 (5)	−0.0049 (4)
Br1	0.0737 (3)	0.0409 (2)	0.0554 (3)	−0.0142 (3)	0.00161 (19)	−0.0071 (3)

Geometric parameters (Å, º) top

C1—C2	1.348 (7)	C8—C9	1.394 (6)
C1—S1	1.692 (5)	C8—C13	1.410 (6)
C1—H1	0.9300	C9—C10	1.406 (6)
C2—C3	1.397 (6)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.362 (6)
C3—C4	1.362 (6)	C10—H10	0.9300
C3—Br1	1.901 (4)	C11—C12	1.382 (6)
C4—C5	1.483 (6)	C11—O2	1.383 (5)
C4—S1	1.728 (4)	C12—C13	1.361 (6)
C5—O1	1.232 (6)	C12—O3	1.374 (5)
C5—C6	1.463 (6)	C13—H13	0.9300
C6—C7	1.341 (6)	C14—O2	1.425 (6)
C6—H6	0.9300	C14—O3	1.442 (6)
C7—C8	1.456 (6)	C14—H14A	0.9700
C7—H7	0.9300	C14—H14B	0.9700

C2—C1—S1	112.9 (3)	C8—C9—C10	122.5 (4)
C2—C1—H1	123.6	C8—C9—H9	118.7
S1—C1—H1	123.6	C10—C9—H9	118.7
C1—C2—C3	111.3 (4)	C11—C10—C9	115.2 (4)
C1—C2—H2	124.3	C11—C10—H10	122.4
C3—C2—H2	124.3	C9—C10—H10	122.4
C4—C3—C2	114.7 (4)	C10—C11—C12	123.3 (4)
C4—C3—Br1	127.0 (3)	C10—C11—O2	126.8 (4)
C2—C3—Br1	118.3 (3)	C12—C11—O2	109.9 (4)
C3—C4—C5	136.8 (4)	C13—C12—O3	128.4 (4)
C3—C4—S1	109.3 (3)	C13—C12—C11	122.1 (4)
C5—C4—S1	113.9 (3)	O3—C12—C11	109.5 (4)
O1—C5—C6	121.3 (4)	C12—C13—C8	116.9 (4)
O1—C5—C4	117.7 (4)	C12—C13—H13	121.5
C6—C5—C4	121.0 (4)	C8—C13—H13	121.5
C7—C6—C5	120.9 (4)	O2—C14—O3	107.4 (4)
C7—C6—H6	119.5	O2—C14—H14A	110.2
C5—C6—H6	119.5	O3—C14—H14A	110.2
C6—C7—C8	129.2 (4)	O2—C14—H14B	110.2
C6—C7—H7	115.4	O3—C14—H14B	110.2
C8—C7—H7	115.4	H14A—C14—H14B	108.5
C9—C8—C13	119.9 (4)	C11—O2—C14	106.6 (3)
C9—C8—C7	117.4 (4)	C12—O3—C14	106.7 (4)
C13—C8—C7	122.6 (4)	C1—S1—C4	91.8 (2)

S1—C1—C2—C3	−2.3 (5)	C9—C10—C11—C12	0.4 (7)
C1—C2—C3—C4	1.8 (6)	C9—C10—C11—O2	−179.5 (4)
C1—C2—C3—Br1	179.3 (3)	C10—C11—C12—C13	−0.4 (7)
C2—C3—C4—C5	178.6 (4)	O2—C11—C12—C13	179.5 (4)
Br1—C3—C4—C5	1.4 (7)	C10—C11—C12—O3	−179.3 (4)
C2—C3—C4—S1	−0.5 (5)	O2—C11—C12—O3	0.6 (5)
Br1—C3—C4—S1	−177.6 (2)	O3—C12—C13—C8	178.8 (4)
C3—C4—C5—O1	−168.1 (5)	C11—C12—C13—C8	0.1 (6)
S1—C4—C5—O1	11.0 (5)	C9—C8—C13—C12	0.2 (6)
C3—C4—C5—C6	13.9 (7)	C7—C8—C13—C12	−179.7 (4)
S1—C4—C5—C6	−167.0 (3)	C10—C11—O2—C14	179.6 (4)
O1—C5—C6—C7	2.5 (7)	C12—C11—O2—C14	−0.3 (5)
C4—C5—C6—C7	−179.6 (4)	O3—C14—O2—C11	0.0 (5)
C5—C6—C7—C8	−177.0 (4)	C13—C12—O3—C14	−179.4 (4)
C6—C7—C8—C9	172.3 (5)	C11—C12—O3—C14	−0.6 (5)
C6—C7—C8—C13	−7.8 (7)	O2—C14—O3—C12	0.4 (5)
C13—C8—C9—C10	−0.2 (7)	C2—C1—S1—C4	1.8 (4)
C7—C8—C9—C10	179.7 (4)	C3—C4—S1—C1	−0.7 (3)
C8—C9—C10—C11	−0.1 (7)	C5—C4—S1—C1	180.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2ⁱ	0.93	2.51	3.420 (6)	167
C14—H14A···O1ⁱⁱ	0.97	2.44	3.400 (6)	171

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

Experimental details

Crystal data
Chemical formula	C₁₄H₉BrO₃S
M_r	337.18
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	291
a, b, c (Å)	4.0013 (3), 11.0211 (9), 14.6931 (11)
β (°)	95.781 (2)
V (Å³)	644.65 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.35
Crystal size (mm)	0.48 × 0.16 × 0.09

Data collection
Diffractometer	Bruker SMART1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.296, 0.753
No. of measured, independent and observed [I > 2σ(I)] reflections	4452, 2684, 2180
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.091, 0.94
No. of reflections	2684
No. of parameters	172
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.43
Absolute structure	Flack (1983), 1127 Friedel pairs
Absolute structure parameter	0.057 (11)

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2ⁱ	0.93	2.51	3.420 (6)	167
C14—H14A···O1ⁱⁱ	0.97	2.44	3.400 (6)	171

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

Acknowledgements

CSC thanks the Department of Studies in Chemistry, University of Mysore, for the provision of research facilities.

References

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