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Acta Cryst. (2007). E63, o3705-o3706    [ doi:10.1107/S1600536807037841 ]

(2E)-1-(3-Bromothien-2-yl)-3-phenylprop-2-en-1-one

R. J. Butcher, J. P. Jasinski, H. S. Yathirajan, B. V. Ashalatha and B. Narayana

Abstract top

The title compound, C13H9BrOS, crystallizes with two independent molecules (A and B) in the asymmetric unit. The mean planes of the 3-bromothien-2-yl and 3-phenyl groups in A and B form dihedral angles of 4.9 (7) and 12.2 (4)°, respectively. The angles between the mean plane of the prop-2-en-1-one group and those of the 3-bromothien-2-yl and 3-phenyl groups are 2.8 (2) and 3.8 (2)°, respectively, in molecule A, and 5.1 (1) and 9.8 (9)° in molecule B. Essentially planar groups of molecule A pack zigzag to similar groups of molecule B along the a axis of the unit cell.

Comment top

Chalcones and their heterocyclic derivatives show numerous biological effects. Among several organic compounds reported for non-linear optical (NLO) property, chalcone derivatives are noticeable materials for their excellent blue light transmittance and good crystallizability. Chalcones provide a necessary configuration to show NLO property with two planar rings connected through a conjugated double bond. The NLO effect in organic molecules originates from a strong intermolecular donor-acceptor interaction, a delocalized π-electron system, and the ability to crystallize in a non-centrosymmetric structure. Secondly, the backbone is usually twisted, and this twist is inherently chiral and often results in these compounds crystallizing in non-centrosymmetric space groups. Substitution on either of the phenyl rings greatly influences non-centrosymmetric crystal packing. It is speculated that, in order to improve the activity, more bulky substituents should be introduced to increase the spontaneous polarization of a non-centrosymmetric crystal structure The molecular hyperpolarizability, β, is strongly influenced not only by the electronic effect, but also by the steric effect of the subsistent. Prompted by this, and in continuation of our quest to synthesize new materials which can find use in the photonics industries, we have synthesized a new chalcone and the present paper reports the crystal structure of a newly synthesized chalcone, (I), C13H9BrOS.

The mean planes of the 3-Bromothien-2-yl and 3-phenyl groups in molecules A and B form dihedral angles of 4.9 (7)° and 12.2 (4)°, respectively, with each other (Fig. 1). The angles between the mean plane of the prop-2-en-1-one group and those of the 3-Bromothien-2-yl and 3-phenyl groups are 2.8 (2)° and 3.8 (2)° in molecule A, and 5.1 (1)° and 9.8 (9)° in molecule B.

The packing diagram displays a zigzag array of mean planes of adjacent planar arranged groups of molecules A located next to mean planes of molecules B located diagonal along the a axis of the unit cell (Fig. 2). The closest centroid-centroid distance of 4.63 (2) Å occurs between the nearby mean planes of the inverted 3-Bromothien-2-yl and 3-phenyl groups for molecule A.

Related literature top

For related structures, see: Baxter et al. (1990); Ng et al. (2006); Yathirajan, Sarojini, Narayana, Ashalatha & Bolte (2006); Yathirajan, Sarojini, Narayana, Bindya & Bolte (2006); Harrison et al. (2006); Butcher et al. (2007a,b,c). For related background, see: Fichou et al. (1988); Goto et al. (1991); Cho et al. (1996); Uchida et al. (1998); Tam et al. (1989); Indira et al. (2002); Opletalova & Sedivy (1999); Butcher, Yathirajan, Sarojini et al. (2006); Butcher et al. (2006a,b).

Experimental top

3-bromo-2-acetylthiophene (10 g, 0.048 mol) in 50 ml me thanol is mixed with benzaldehyde (5.0 g, 0.048 mol) and the mixture was treated with an 10 ml of 30% potassium hydroxide solution at 278 K (Fig. 3). The reaction mixture was then brought to room temperature and stirred for 3 h. The solid precipated was filtered and washed with water, dried and recrytallized from toluene (m.p.: 339 K).

Refinement top

The high value of Rint is probably due to poor crystal quality. The H atoms were included in the riding model approximation with C—H = 0.95 Å, and with Uiso(H) = 1.18–1.21Ueq(C). The maximum residual electron density peaks of 2.40 and −1.49 e Å3, were located at 0.90 and 0.76 Å from the Br1A and Br1B atoms, respectively.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top
[Figure 1] Fig. 1. Molecular structure of C13H9BrOS, (I), showing atom labeling and 50% probability displacement ellipsoids for independent molecules A and B in the asymmetric unit.
[Figure 2] Fig. 2. Packing diagram of C13H9BrOS viewed down the b axis.
[Figure 3] Fig. 3. Synthesis scheme of C13H9BrOS.
(2E)-1-(3-Bromothien-2-yl)-3-phenylprop-2-en-1-one top
Crystal data top
C13H9BrOSDx = 1.683 Mg m−3
Mr = 293.17Mo Kα radiation
λ = 0.71073 Å
Orthorhombic, Pca21Cell parameters from 5433 reflections
a = 17.321 (4) Åθ = 2.4–28.3º
b = 5.4295 (12) ŵ = 3.71 mm−1
c = 24.600 (5) ÅT = 123 K
V = 2313.5 (9) Å3Rectangular, colourless
Z = 80.69 × 0.32 × 0.10 mm
F000 = 1168
Data collection top
Bruker APEXII CCD area-detector
diffractometer		5590 independent reflections
Radiation source: fine-focus sealed tube4041 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.105
T = 123 Kθmax = 28.7º
φ and ω scansθmin = 2.4º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −23→23
Tmin = 0.335, Tmax = 1.000k = −5→7
17031 measured reflectionsl = −31→33
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.069  w = 1/[σ2(Fo2) + (0.114P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.178(Δ/σ)max = 0.001
S = 0.99Δρmax = 2.41 e Å−3
5590 reflectionsΔρmin = −1.49 e Å−3
289 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983), 2580 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.014 (15)
Secondary atom site location: difference Fourier map
Crystal data top
C13H9BrOSV = 2313.5 (9) Å3
Mr = 293.17Z = 8
Orthorhombic, Pca21Mo Kα
a = 17.321 (4) ŵ = 3.71 mm−1
b = 5.4295 (12) ÅT = 123 K
c = 24.600 (5) Å0.69 × 0.32 × 0.10 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer		5590 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4041 reflections with I > 2σ(I)
Tmin = 0.335, Tmax = 1.000Rint = 0.105
17031 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.069H-atom parameters constrained
wR(F2) = 0.178Δρmax = 2.41 e Å−3
S = 0.99Δρmin = −1.49 e Å−3
5590 reflectionsAbsolute structure: Flack (1983), 2580 Friedel pairs
289 parametersFlack parameter: 0.014 (15)
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 > 2sigma(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
xyzUiso*/Ueq
Br1A0.19487 (4)−0.04060 (15)0.04400 (3)0.0344 (2)
Br1B−0.10871 (5)0.54938 (16)0.45589 (3)0.0362 (2)
S1A0.25796 (9)−0.2937 (3)0.20837 (8)0.0247 (4)
S1B−0.15628 (9)0.7896 (3)0.28805 (8)0.0242 (4)
O1A0.1645 (3)0.1132 (10)0.2363 (2)0.0248 (10)
O1B−0.0611 (3)0.3863 (11)0.2652 (2)0.0309 (12)
C1A0.2977 (4)−0.4717 (15)0.1588 (4)0.0274 (17)
H1AA0.3305−0.60850.16560.033*
C2A0.2771 (4)−0.3951 (16)0.1081 (3)0.0291 (17)
H2AA0.2935−0.47290.07550.035*
C3A0.2279 (4)−0.1846 (13)0.1098 (3)0.0218 (14)
C4A0.2109 (4)−0.1080 (15)0.1615 (3)0.0224 (15)
C5A0.1631 (3)0.0939 (14)0.1870 (3)0.0220 (15)
C6A0.1159 (3)0.2476 (14)0.1517 (3)0.0233 (15)
H6AA0.11610.22090.11350.028*
C7A0.0719 (4)0.4273 (14)0.1731 (3)0.0258 (16)
H7AA0.07410.44790.21140.031*
C8A0.0203 (4)0.5969 (14)0.1426 (3)0.0234 (15)
C9A−0.0133 (3)0.7948 (14)0.1707 (4)0.0282 (16)
H9AA−0.00330.81840.20830.034*
C10A−0.0618 (4)0.9568 (14)0.1427 (4)0.0323 (19)
H10A−0.08561.08850.16170.039*
C11A−0.0754 (4)0.9286 (14)0.0882 (4)0.0329 (19)
H11A−0.10641.04460.06930.040*
C12A−0.0432 (4)0.7272 (16)0.0604 (3)0.0350 (19)
H12A−0.05410.70310.02290.042*
C13A0.0046 (4)0.5632 (16)0.0877 (3)0.0321 (18)
H13A0.02670.42780.06880.039*
C1B−0.1999 (4)0.9667 (14)0.3363 (4)0.0276 (16)
H1BA−0.23301.10050.32760.033*
C2B−0.1839 (4)0.9028 (15)0.3871 (3)0.0253 (16)
H2BA−0.20260.98520.41850.030*
C3B−0.1345 (4)0.6920 (14)0.3877 (3)0.0243 (14)
C4B−0.1132 (3)0.6062 (15)0.3372 (3)0.0220 (15)
C5B−0.0641 (4)0.4081 (12)0.3151 (3)0.0206 (14)
C6B−0.0212 (4)0.2400 (15)0.3516 (3)0.0272 (16)
H6BA−0.02640.25680.38990.033*
C7B0.0246 (4)0.0655 (14)0.3314 (3)0.0250 (15)
H7BA0.02600.05080.29290.030*
C8B0.0732 (3)−0.1073 (13)0.3625 (3)0.0252 (16)
C9B0.1140 (4)−0.2874 (13)0.3332 (3)0.0254 (15)
H9BA0.1109−0.29240.29460.030*
C10B0.1595 (4)−0.4607 (15)0.3615 (4)0.0330 (18)
H10B0.1873−0.58220.34170.040*
C11B0.1642 (4)−0.4563 (15)0.4168 (4)0.0354 (19)
H11B0.1947−0.57410.43560.042*
C12B0.1238 (5)−0.2768 (18)0.4451 (4)0.046 (2)
H12B0.1277−0.27000.48360.055*
C13B0.0778 (5)−0.1073 (16)0.4182 (4)0.0320 (17)
H13B0.04920.01020.43850.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br1A0.0368 (4)0.0379 (5)0.0284 (4)0.0097 (3)−0.0013 (3)0.0006 (4)
Br1B0.0410 (4)0.0391 (5)0.0286 (4)0.0139 (3)0.0015 (3)0.0031 (5)
S1A0.0172 (7)0.0230 (9)0.0340 (9)0.0013 (6)−0.0024 (6)0.0024 (8)
S1B0.0190 (7)0.0232 (9)0.0303 (9)0.0022 (6)−0.0020 (6)−0.0003 (7)
O1A0.020 (2)0.022 (3)0.032 (3)0.003 (2)0.003 (2)0.001 (2)
O1B0.031 (3)0.027 (3)0.034 (3)0.011 (2)0.004 (2)0.001 (2)
C1A0.009 (3)0.028 (4)0.045 (5)0.005 (3)−0.002 (3)−0.002 (3)
C2A0.017 (3)0.033 (5)0.037 (4)−0.005 (3)0.000 (3)−0.004 (3)
C3A0.021 (3)0.017 (4)0.027 (4)0.000 (2)−0.003 (3)0.006 (3)
C4A0.018 (3)0.021 (4)0.029 (4)−0.008 (3)0.002 (3)−0.008 (3)
C5A0.007 (2)0.026 (4)0.034 (4)0.001 (2)0.001 (2)0.002 (3)
C6A0.017 (3)0.021 (4)0.031 (4)0.003 (3)0.000 (3)−0.001 (3)
C7A0.016 (3)0.022 (4)0.040 (4)0.001 (2)−0.002 (3)0.001 (3)
C8A0.013 (3)0.022 (4)0.035 (4)0.000 (2)0.002 (3)0.003 (3)
C9A0.012 (3)0.021 (4)0.051 (5)−0.004 (3)0.002 (3)−0.001 (3)
C10A0.014 (3)0.020 (4)0.063 (6)0.003 (3)0.007 (3)0.011 (4)
C11A0.019 (3)0.020 (4)0.060 (6)0.001 (3)0.000 (3)0.014 (4)
C12A0.029 (3)0.038 (5)0.038 (5)0.005 (3)0.000 (3)0.011 (3)
C13A0.027 (3)0.030 (5)0.040 (5)0.004 (3)0.003 (3)0.004 (4)
C1B0.018 (3)0.020 (4)0.045 (5)0.000 (3)−0.002 (3)−0.001 (3)
C2B0.015 (3)0.025 (4)0.035 (4)−0.005 (3)0.007 (3)−0.006 (3)
C3B0.023 (3)0.021 (4)0.028 (4)−0.007 (3)−0.003 (3)0.003 (3)
C4B0.008 (2)0.022 (4)0.036 (4)0.000 (2)0.002 (2)0.006 (3)
C5B0.021 (3)0.007 (3)0.034 (4)−0.002 (2)0.000 (3)−0.003 (3)
C6B0.020 (3)0.030 (4)0.032 (4)0.005 (3)−0.005 (3)0.000 (3)
C7B0.014 (3)0.025 (4)0.036 (4)0.001 (3)−0.002 (3)−0.001 (3)
C8B0.012 (3)0.011 (3)0.053 (5)0.003 (2)−0.003 (3)−0.004 (3)
C9B0.018 (3)0.012 (3)0.046 (4)0.000 (2)0.004 (3)−0.001 (3)
C10B0.014 (3)0.025 (4)0.060 (6)0.003 (3)0.001 (3)0.001 (4)
C11B0.020 (3)0.030 (5)0.056 (6)0.009 (3)−0.003 (3)0.004 (4)
C12B0.050 (5)0.038 (5)0.050 (6)0.019 (4)−0.009 (4)0.006 (4)
C13B0.033 (4)0.023 (4)0.039 (4)0.015 (3)−0.009 (3)−0.008 (3)
Geometric parameters (Å, °) top
Br1A—C3A1.886 (7)C11A—H11A0.9500
Br1B—C3B1.900 (7)C12A—C13A1.389 (11)
S1A—C1A1.702 (8)C12A—H12A0.9500
S1A—C4A1.736 (8)C13A—H13A0.9500
S1B—C1B1.705 (8)C1B—C2B1.324 (12)
S1B—C4B1.735 (8)C1B—H1BA0.9500
O1A—C5A1.216 (9)C2B—C3B1.429 (11)
O1B—C5B1.235 (9)C2B—H2BA0.9500
C1A—C2A1.361 (12)C3B—C4B1.378 (11)
C1A—H1AA0.9500C4B—C5B1.475 (10)
C2A—C3A1.426 (10)C5B—C6B1.480 (10)
C2A—H2AA0.9500C6B—C7B1.332 (10)
C3A—C4A1.371 (10)C6B—H6BA0.9500
C4A—C5A1.510 (10)C7B—C8B1.476 (10)
C5A—C6A1.457 (10)C7B—H7BA0.9500
C6A—C7A1.345 (10)C8B—C13B1.371 (12)
C6A—H6AA0.9500C8B—C9B1.406 (10)
C7A—C8A1.487 (10)C9B—C10B1.412 (11)
C7A—H7AA0.9500C9B—H9BA0.9500
C8A—C13A1.390 (11)C10B—C11B1.363 (13)
C8A—C9A1.403 (10)C10B—H10B0.9500
C9A—C10A1.397 (11)C11B—C12B1.388 (12)
C9A—H9AA0.9500C11B—H11B0.9500
C10A—C11A1.370 (13)C12B—C13B1.386 (11)
C10A—H10A0.9500C12B—H12B0.9500
C11A—C12A1.405 (12)C13B—H13B0.9500
C1A—S1A—C4A92.5 (4)C8A—C13A—H13A119.9
C1B—S1B—C4B91.7 (4)C2B—C1B—S1B114.6 (6)
C2A—C1A—S1A112.1 (6)C2B—C1B—H1BA122.7
C2A—C1A—H1AA123.9S1B—C1B—H1BA122.7
S1A—C1A—H1AA123.9C1B—C2B—C3B110.2 (7)
C1A—C2A—C3A112.0 (7)C1B—C2B—H2BA124.9
C1A—C2A—H2AA124.0C3B—C2B—H2BA124.9
C3A—C2A—H2AA124.0C4B—C3B—C2B114.9 (7)
C4A—C3A—C2A113.5 (6)C4B—C3B—Br1B126.5 (6)
C4A—C3A—Br1A127.2 (6)C2B—C3B—Br1B118.5 (6)
C2A—C3A—Br1A119.3 (5)C3B—C4B—C5B137.1 (7)
C3A—C4A—C5A136.4 (7)C3B—C4B—S1B108.6 (6)
C3A—C4A—S1A109.8 (6)C5B—C4B—S1B114.2 (6)
C5A—C4A—S1A113.7 (5)O1B—C5B—C4B117.4 (6)
O1A—C5A—C6A123.8 (6)O1B—C5B—C6B121.5 (6)
O1A—C5A—C4A117.8 (6)C4B—C5B—C6B121.1 (6)
C6A—C5A—C4A118.3 (7)C7B—C6B—C5B120.7 (7)
C7A—C6A—C5A120.0 (7)C7B—C6B—H6BA119.6
C7A—C6A—H6AA120.0C5B—C6B—H6BA119.6
C5A—C6A—H6AA120.0C6B—C7B—C8B126.8 (8)
C6A—C7A—C8A126.4 (7)C6B—C7B—H7BA116.6
C6A—C7A—H7AA116.8C8B—C7B—H7BA116.6
C8A—C7A—H7AA116.8C13B—C8B—C9B118.9 (7)
C13A—C8A—C9A119.9 (7)C13B—C8B—C7B123.5 (7)
C13A—C8A—C7A121.7 (7)C9B—C8B—C7B117.5 (7)
C9A—C8A—C7A118.4 (7)C8B—C9B—C10B119.4 (8)
C10A—C9A—C8A119.2 (8)C8B—C9B—H9BA120.3
C10A—C9A—H9AA120.4C10B—C9B—H9BA120.3
C8A—C9A—H9AA120.4C11B—C10B—C9B120.9 (7)
C11A—C10A—C9A121.1 (8)C11B—C10B—H10B119.5
C11A—C10A—H10A119.5C9B—C10B—H10B119.5
C9A—C10A—H10A119.5C10B—C11B—C12B118.9 (8)
C10A—C11A—C12A119.6 (7)C10B—C11B—H11B120.5
C10A—C11A—H11A120.2C12B—C11B—H11B120.5
C12A—C11A—H11A120.2C13B—C12B—C11B121.1 (9)
C13A—C12A—C11A120.0 (8)C13B—C12B—H12B119.5
C13A—C12A—H12A120.0C11B—C12B—H12B119.5
C11A—C12A—H12A120.0C8B—C13B—C12B120.7 (8)
C12A—C13A—C8A120.1 (8)C8B—C13B—H13B119.6
C12A—C13A—H13A119.9C12B—C13B—H13B119.6
C4A—S1A—C1A—C2A0.3 (6)C4B—S1B—C1B—C2B1.1 (6)
S1A—C1A—C2A—C3A0.4 (8)S1B—C1B—C2B—C3B−1.6 (8)
C1A—C2A—C3A—C4A−1.2 (9)C1B—C2B—C3B—C4B1.4 (9)
C1A—C2A—C3A—Br1A178.0 (5)C1B—C2B—C3B—Br1B−175.8 (5)
C2A—C3A—C4A—C5A−179.2 (7)C2B—C3B—C4B—C5B178.3 (7)
Br1A—C3A—C4A—C5A1.6 (12)Br1B—C3B—C4B—C5B−4.8 (12)
C2A—C3A—C4A—S1A1.4 (7)C2B—C3B—C4B—S1B−0.6 (7)
Br1A—C3A—C4A—S1A−177.7 (4)Br1B—C3B—C4B—S1B176.3 (4)
C1A—S1A—C4A—C3A−1.0 (5)C1B—S1B—C4B—C3B−0.2 (5)
C1A—S1A—C4A—C5A179.5 (5)C1B—S1B—C4B—C5B−179.4 (5)
C3A—C4A—C5A—O1A−176.5 (7)C3B—C4B—C5B—O1B178.2 (8)
S1A—C4A—C5A—O1A2.8 (8)S1B—C4B—C5B—O1B−2.9 (8)
C3A—C4A—C5A—C6A5.9 (12)C3B—C4B—C5B—C6B−0.8 (12)
S1A—C4A—C5A—C6A−174.8 (5)S1B—C4B—C5B—C6B178.1 (5)
O1A—C5A—C6A—C7A1.8 (11)O1B—C5B—C6B—C7B2.7 (11)
C4A—C5A—C6A—C7A179.2 (6)C4B—C5B—C6B—C7B−178.3 (7)
C5A—C6A—C7A—C8A−179.3 (6)C5B—C6B—C7B—C8B177.1 (7)
C6A—C7A—C8A—C13A8.7 (11)C6B—C7B—C8B—C13B−0.6 (12)
C6A—C7A—C8A—C9A−171.5 (7)C6B—C7B—C8B—C9B176.4 (7)
C13A—C8A—C9A—C10A−0.5 (10)C13B—C8B—C9B—C10B−1.0 (10)
C7A—C8A—C9A—C10A179.7 (6)C7B—C8B—C9B—C10B−178.2 (6)
C8A—C9A—C10A—C11A−1.6 (10)C8B—C9B—C10B—C11B0.2 (11)
C9A—C10A—C11A—C12A3.0 (11)C9B—C10B—C11B—C12B−0.4 (12)
C10A—C11A—C12A—C13A−2.5 (11)C10B—C11B—C12B—C13B1.4 (13)
C11A—C12A—C13A—C8A0.4 (12)C9B—C8B—C13B—C12B2.1 (12)
C9A—C8A—C13A—C12A1.0 (11)C7B—C8B—C13B—C12B179.1 (8)
C7A—C8A—C13A—C12A−179.2 (7)C11B—C12B—C13B—C8B−2.3 (14)
Acknowledgements top

BVA thanks Mangalore University for access to their research facilities. RJB acknowledges the Laboratory for the Structure of Matter at the Naval Research Laboratory for access to their diffractometers.

references
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