organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

(E)-3-(3,4-Di­meth­oxy­phen­yl)-1-(2-thien­yl)prop-2-en-1-one

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India
*Correspondence e-mail: hkfun@usm.my

(Received 1 July 2008; accepted 4 July 2008; online 9 July 2008)

The title compound, C15H14O3S, has two symmetry-independent mol­ecules in the asymmetric unit with almost identical geometry. The dihedral angle between the benzene and thio­phene rings is 1.61 (11)° in one mol­ecule and 7.21 (11)° in the other. In both mol­ecules, C—H⋯O hydrogen bonds generate rings of graph-set motif S(5). The crystal structure is stabilized by C—H⋯O hydrogen bonds, C—H⋯π inter­actions and ππ inter­actions involving the benzene and thio­phene rings, with centroid–centroid distances of 3.5249 (13) and 3.6057 (13) Å.

Related literature

For related literature on the biological and non-linear optical properties of chalcone derivatives, see: Agrinskaya et al. (1999[Agrinskaya, N. V., Lukoshkin, V. A., Kudryavtsev, V. V., Nosova, G. I., Solovskaya, N. A. & Yakimanski, A. V. (1999). Phys. Solid State, 41, 1914-1917.]); Chopra et al. (2007[Chopra, D., Mohan, T. P., Vishalakshi, B. & Guru Row, T. N. (2007). Acta Cryst. C63, o704-o710.]); Patil et al. (2006[Patil, P. S., Teh, J. B.-J., Fun, H.-K., Razak, I. A. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o896-o898.]); Patil, Ng et al. (2007[Patil, P. S., Ng, S.-L., Razak, I. A., Fun, H.-K. & Dharmaprakash, S. M. (2007). Acta Cryst. E63, o59-o60.]); Patil, Fun et al. (2007[Patil, P. S., Fun, H.-K., Chantrapromma, S. & Dharmaprakash, S. M. (2007). Acta Cryst. E63, o2497-o2498.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-S19.]). For graph-set analysis of hydrogen-bond patterns, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C15H14O3S

  • Mr = 274.32

  • Monoclinic, P 21 /n

  • a = 12.1509 (3) Å

  • b = 14.3118 (3) Å

  • c = 16.3692 (4) Å

  • β = 106.570 (2)°

  • V = 2728.41 (11) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 100.0 (1) K

  • 0.60 × 0.17 × 0.11 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.871, Tmax = 0.974

  • 31879 measured reflections

  • 7997 independent reflections

  • 4723 reflections with I > 2σ(I)

  • Rint = 0.074

Refinement
  • R[F2 > 2σ(F2)] = 0.060

  • wR(F2) = 0.158

  • S = 1.07

  • 7997 reflections

  • 347 parameters

  • H-atom parameters constrained

  • Δρmax = 0.46 e Å−3

  • Δρmin = −0.44 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C7A—H7AA⋯O1A 0.93 2.43 2.792 (3) 103
C1B—H1BA⋯O1Ai 0.93 2.36 3.261 (3) 162
C7B—H7BA⋯O1B 0.93 2.47 2.816 (3) 102
C14B—H14F⋯O1Bii 0.96 2.53 3.401 (3) 151
C15A—H15ACg1iii 0.96 2.92 3.616 (3) 130
C10A—H10ACg3iv 0.93 2.84 3.636 (3) 144
C3A—H3AACg4 0.93 2.79 3.370 (3) 122
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1; (iii) [x-{\script{3\over 2}}, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]; (iv) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]. Cg1, Cg3 and Cg4 are the centroids of the S1A/C1A–C4A, S1B/C1B–C4B and C8B–C13B rings, respectively.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

Supporting information


Comment top

The synthesis and structural studies of chalcone derivatives have been of immense interest because of their biological as well as their increasingly important nonlinear optical properties (Agrinskaya et al., 1999; Chopra et al. 2007). We have previously reported the crystal structures of D–π–A type chalcone derivatives (Patil et al.. 2006; Patil, Ng et al., 2007; Patil, Fun et al., 2007). In continuation of our interest in these compounds, we report herein the crystal structure of the title compound, (I).

There are two independent molecules (A and B) in the asymmetric unit of (I), with similar geometries (Fig. 1). The bond lengths and angles are found to have normal values (Allen et al., 1987). The thiophene rings in both the molecules are planar, with a maximum deviation of 0.002 (3) Å for atom C2A and -0.007 (3) Å for atom C3B. The dihedral angle between the benzene and thiophene rings is 1.61 (11)° in molecule A and 7.21 (11)° in molecule B. In each of the independent molecule, an intramolecular C—H···O hydrogen bond generates an S(5) ring motif (Bernstein et al., 1995).

The crystal structure is consolidated by weak C—H···O and C—H···π interactions (Table 1). The packing is further strengthened by ππ interactions between the S1A/C1A–C4A (centroid Cg1) and C8A–C13A (centroid Cg2) rings [Cg1···Cg2i = 3.5249 (13) Å] and between the S1B/C1B–C4B (centroid Cg3) and C8B–C13B (centroid Cg4) rings [Cg3···Cg4ii = 3.6057 (13) Å] [symmetry codes: (i) -x, 1-y, -z; (ii) -x, 1-y, -z].

Related literature top

For related literature on the biological and nonlinear optical properties of chalcone derivatives, see: Agrinskaya et al. (1999); Chopra et al. (2007); Patil et al. (2006); Patil, Ng et al. (2007); Patil, Fun et al. (2007). For bond-length data, see: Allen et al. (1987). For graph-set analysis of hydrogen-bond patterns, see: Bernstein et al. (1995).

Experimental top

The title compound was synthesized by the condensation of 3,4-dimethoxybenzaldehyde (0.01 mol, 1.66 g) with 2-acetylthiophene (0.01 mol, 1.07 ml) in methanol (60 ml) in the presence of a catalytic amount of sodium hydroxide solution (5 ml, 30%). After stirring for 6 h, the contents of the flask were poured into ice-cold water (500 ml) and left to stand for 5 h. The resulting crude solid was filtered and dried. The compound was recrystallized from acetone.

Refinement top

H atoms were positioned geometrically [C-H = 0.93-0.96 Å] and refined using a riding model, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(Cmethyl). A rotating group model was used for the methyl groups.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.
(E)-3-(3,4-Dimethoxyphenyl)-1-(2-thienyl)prop-2-en-1-one top
Crystal data top
C15H14O3SF(000) = 1152
Mr = 274.32Dx = 1.336 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3182 reflections
a = 12.1509 (3) Åθ = 2.3–22.9°
b = 14.3118 (3) ŵ = 0.24 mm1
c = 16.3692 (4) ÅT = 100 K
β = 106.570 (2)°Needle, white
V = 2728.41 (11) Å30.60 × 0.17 × 0.11 mm
Z = 8
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
7997 independent reflections
Radiation source: fine-focus sealed tube4723 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.074
ϕ and ω scansθmax = 30.1°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1617
Tmin = 0.871, Tmax = 0.974k = 2020
31879 measured reflectionsl = 2323
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0645P)2 + 0.0849P]
where P = (Fo2 + 2Fc2)/3
7997 reflections(Δ/σ)max = 0.001
347 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = 0.44 e Å3
Crystal data top
C15H14O3SV = 2728.41 (11) Å3
Mr = 274.32Z = 8
Monoclinic, P21/nMo Kα radiation
a = 12.1509 (3) ŵ = 0.24 mm1
b = 14.3118 (3) ÅT = 100 K
c = 16.3692 (4) Å0.60 × 0.17 × 0.11 mm
β = 106.570 (2)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
7997 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
4723 reflections with I > 2σ(I)
Tmin = 0.871, Tmax = 0.974Rint = 0.074
31879 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.158H-atom parameters constrained
S = 1.07Δρmax = 0.46 e Å3
7997 reflectionsΔρmin = 0.44 e Å3
347 parameters
Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
xyzUiso*/Ueq
S1A0.30263 (5)0.34458 (4)0.21155 (4)0.03061 (17)
O1A0.29234 (14)0.52178 (12)0.12000 (11)0.0341 (4)
O2A0.29137 (13)0.76488 (11)0.01772 (10)0.0271 (4)
O3A0.23198 (13)0.90679 (11)0.08963 (10)0.0263 (4)
C1A0.2263 (2)0.26572 (18)0.24872 (16)0.0347 (6)
H1AA0.25820.21240.27870.042*
C2A0.1135 (2)0.28805 (18)0.23049 (18)0.0381 (6)
H2AA0.06020.25160.24700.046*
C3A0.08511 (19)0.37196 (15)0.18408 (14)0.0241 (5)
H3AA0.01170.39750.16600.029*
C4A0.18303 (19)0.41151 (16)0.16895 (14)0.0254 (5)
C5A0.1974 (2)0.49958 (16)0.12684 (14)0.0261 (5)
C6A0.09567 (19)0.56023 (16)0.09447 (14)0.0276 (5)
H6AA0.02440.54110.09870.033*
C7A0.1065 (2)0.64255 (17)0.05911 (15)0.0294 (5)
H7AA0.18000.65720.05650.035*
C8A0.01813 (19)0.71264 (17)0.02396 (14)0.0273 (5)
C9A0.0492 (2)0.79240 (17)0.01259 (15)0.0302 (5)
H9AA0.12550.80110.01140.036*
C10A0.03157 (19)0.85911 (17)0.05077 (14)0.0279 (5)
H10A0.00960.91190.07530.034*
C11A0.14488 (19)0.84704 (16)0.05229 (13)0.0241 (5)
C12A0.17800 (18)0.76786 (16)0.01398 (14)0.0228 (5)
C13A0.09658 (19)0.70150 (16)0.02383 (14)0.0248 (5)
H13A0.11810.64920.04930.030*
C14A0.3308 (2)0.67985 (16)0.01146 (17)0.0321 (6)
H14A0.41240.68300.00200.048*
H14B0.29370.67200.07120.048*
H14C0.31270.62780.01940.048*
C15A0.2024 (2)0.98748 (17)0.13146 (16)0.0323 (6)
H15A0.26981.02470.15470.048*
H15B0.17190.96770.17660.048*
H15C0.14591.02380.09100.048*
S1B0.37037 (5)0.38880 (4)0.72047 (4)0.03122 (17)
O1B0.16770 (14)0.30240 (11)0.59734 (11)0.0326 (4)
O2B0.10219 (14)0.60874 (11)0.21110 (10)0.0298 (4)
O3B0.24951 (13)0.49172 (11)0.12281 (10)0.0307 (4)
C1B0.45590 (19)0.48496 (18)0.73969 (15)0.0318 (6)
H1BA0.51990.49130.78680.038*
C2B0.42056 (19)0.55139 (17)0.67877 (15)0.0293 (5)
H2BA0.45780.60820.67910.035*
C3B0.32112 (18)0.52442 (15)0.61500 (14)0.0236 (5)
H3BA0.28470.56210.56900.028*
C4B0.28323 (18)0.43643 (15)0.62777 (14)0.0230 (5)
C5B0.18737 (18)0.38180 (16)0.57549 (14)0.0240 (5)
C6B0.11733 (18)0.42482 (16)0.49650 (14)0.0240 (5)
H6BA0.13160.48630.48420.029*
C7B0.03331 (19)0.37724 (16)0.44176 (15)0.0262 (5)
H7BA0.02140.31650.45770.031*
C8B0.04199 (18)0.40867 (16)0.36023 (14)0.0236 (5)
C9B0.12424 (19)0.34745 (16)0.31244 (14)0.0254 (5)
H9BA0.13150.28840.33400.030*
C10B0.19590 (19)0.37269 (16)0.23295 (14)0.0249 (5)
H10B0.25020.33070.20180.030*
C11B0.18609 (18)0.45996 (16)0.20059 (14)0.0237 (5)
C12B0.10419 (18)0.52376 (15)0.24885 (14)0.0218 (5)
C13B0.03375 (18)0.49828 (16)0.32695 (14)0.0231 (5)
H13B0.02000.54060.35830.028*
C14B0.0190 (2)0.67467 (17)0.25647 (16)0.0336 (6)
H14D0.02300.73000.22260.050*
H14E0.05630.64780.26830.050*
H14F0.03450.69060.30910.050*
C15B0.3363 (2)0.43030 (18)0.07416 (16)0.0374 (6)
H15D0.37300.45830.01990.056*
H15E0.39230.41930.10430.056*
H15F0.30200.37200.06560.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0259 (3)0.0293 (3)0.0321 (3)0.0024 (2)0.0008 (2)0.0001 (3)
O1A0.0258 (9)0.0367 (10)0.0373 (10)0.0039 (7)0.0047 (7)0.0070 (8)
O2A0.0241 (8)0.0226 (9)0.0342 (9)0.0016 (7)0.0076 (7)0.0018 (7)
O3A0.0254 (8)0.0255 (9)0.0270 (9)0.0027 (7)0.0060 (7)0.0050 (7)
C1A0.0423 (15)0.0250 (13)0.0364 (15)0.0033 (11)0.0104 (12)0.0002 (11)
C2A0.0387 (15)0.0299 (15)0.0513 (17)0.0063 (11)0.0219 (13)0.0096 (13)
C3A0.0225 (11)0.0194 (12)0.0285 (12)0.0018 (9)0.0041 (9)0.0080 (10)
C4A0.0240 (11)0.0258 (13)0.0236 (12)0.0038 (9)0.0021 (9)0.0081 (10)
C5A0.0283 (12)0.0251 (13)0.0205 (11)0.0043 (10)0.0001 (9)0.0052 (10)
C6A0.0247 (11)0.0285 (14)0.0261 (12)0.0042 (10)0.0015 (9)0.0030 (10)
C7A0.0256 (12)0.0331 (14)0.0261 (13)0.0038 (10)0.0017 (10)0.0016 (11)
C8A0.0245 (11)0.0309 (14)0.0214 (12)0.0037 (10)0.0015 (9)0.0015 (10)
C9A0.0237 (12)0.0369 (15)0.0271 (13)0.0002 (10)0.0027 (10)0.0032 (11)
C10A0.0276 (12)0.0289 (13)0.0251 (12)0.0016 (10)0.0040 (10)0.0036 (10)
C11A0.0262 (11)0.0273 (13)0.0157 (11)0.0042 (10)0.0009 (9)0.0006 (9)
C12A0.0229 (11)0.0249 (12)0.0203 (11)0.0015 (9)0.0054 (9)0.0034 (9)
C13A0.0300 (12)0.0215 (12)0.0220 (12)0.0008 (9)0.0059 (9)0.0002 (9)
C14A0.0343 (13)0.0246 (13)0.0423 (15)0.0019 (10)0.0185 (12)0.0014 (11)
C15A0.0313 (13)0.0298 (14)0.0351 (14)0.0028 (10)0.0082 (11)0.0120 (11)
S1B0.0260 (3)0.0321 (4)0.0313 (3)0.0046 (2)0.0013 (2)0.0055 (3)
O1B0.0321 (9)0.0229 (9)0.0387 (10)0.0015 (7)0.0036 (8)0.0055 (8)
O2B0.0342 (9)0.0224 (9)0.0284 (9)0.0067 (7)0.0017 (7)0.0020 (7)
O3B0.0332 (9)0.0256 (9)0.0260 (9)0.0052 (7)0.0034 (7)0.0010 (7)
C1B0.0221 (11)0.0390 (15)0.0312 (13)0.0035 (10)0.0027 (10)0.0071 (12)
C2B0.0239 (11)0.0277 (13)0.0344 (13)0.0022 (10)0.0054 (10)0.0032 (11)
C3B0.0219 (11)0.0222 (12)0.0243 (12)0.0016 (9)0.0027 (9)0.0017 (10)
C4B0.0227 (11)0.0224 (12)0.0233 (12)0.0032 (9)0.0058 (9)0.0011 (9)
C5B0.0236 (11)0.0230 (12)0.0263 (12)0.0019 (9)0.0083 (9)0.0018 (10)
C6B0.0253 (11)0.0200 (12)0.0253 (12)0.0010 (9)0.0048 (9)0.0014 (9)
C7B0.0263 (12)0.0198 (12)0.0315 (13)0.0013 (9)0.0068 (10)0.0034 (10)
C8B0.0225 (11)0.0257 (13)0.0220 (11)0.0024 (9)0.0053 (9)0.0029 (9)
C9B0.0262 (11)0.0233 (12)0.0251 (12)0.0024 (9)0.0048 (9)0.0001 (10)
C10B0.0240 (11)0.0211 (12)0.0274 (12)0.0037 (9)0.0036 (9)0.0055 (10)
C11B0.0229 (11)0.0239 (12)0.0218 (11)0.0003 (9)0.0025 (9)0.0007 (10)
C12B0.0247 (11)0.0164 (11)0.0255 (12)0.0007 (9)0.0091 (9)0.0014 (9)
C13B0.0229 (11)0.0214 (12)0.0240 (12)0.0037 (9)0.0052 (9)0.0041 (9)
C14B0.0400 (14)0.0223 (13)0.0343 (14)0.0124 (11)0.0041 (11)0.0027 (11)
C15B0.0413 (15)0.0332 (15)0.0284 (14)0.0105 (12)0.0051 (11)0.0002 (11)
Geometric parameters (Å, º) top
S1A—C1A1.681 (3)S1B—C1B1.699 (3)
S1A—C4A1.714 (2)S1B—C4B1.724 (2)
O1A—C5A1.232 (3)O1B—C5B1.235 (3)
O2A—C12A1.362 (2)O2B—C12B1.368 (3)
O2A—C14A1.439 (3)O2B—C14B1.426 (3)
O3A—C11A1.362 (3)O3B—C11B1.364 (3)
O3A—C15A1.439 (3)O3B—C15B1.429 (3)
C1A—C2A1.355 (3)C1B—C2B1.356 (3)
C1A—H1AA0.93C1B—H1BA0.93
C2A—C3A1.410 (3)C2B—C3B1.407 (3)
C2A—H2AA0.93C2B—H2BA0.93
C3A—C4A1.402 (3)C3B—C4B1.377 (3)
C3A—H3AA0.93C3B—H3BA0.93
C4A—C5A1.471 (3)C4B—C5B1.460 (3)
C5A—C6A1.479 (3)C5B—C6B1.466 (3)
C6A—C7A1.336 (3)C6B—C7B1.337 (3)
C6A—H6AA0.93C6B—H6BA0.93
C7A—C8A1.462 (3)C7B—C8B1.457 (3)
C7A—H7AA0.93C7B—H7BA0.93
C8A—C9A1.390 (3)C8B—C9B1.390 (3)
C8A—C13A1.402 (3)C8B—C13B1.408 (3)
C9A—C10A1.384 (3)C9B—C10B1.391 (3)
C9A—H9AA0.93C9B—H9BA0.93
C10A—C11A1.381 (3)C10B—C11B1.375 (3)
C10A—H10A0.93C10B—H10B0.93
C11A—C12A1.408 (3)C11B—C12B1.414 (3)
C12A—C13A1.384 (3)C12B—C13B1.370 (3)
C13A—H13A0.93C13B—H13B0.93
C14A—H14A0.96C14B—H14D0.96
C14A—H14B0.96C14B—H14E0.96
C14A—H14C0.96C14B—H14F0.96
C15A—H15A0.96C15B—H15D0.96
C15A—H15B0.96C15B—H15E0.96
C15A—H15C0.96C15B—H15F0.96
C1A—S1A—C4A91.80 (12)C1B—S1B—C4B91.86 (12)
C12A—O2A—C14A116.11 (17)C12B—O2B—C14B117.02 (18)
C11A—O3A—C15A116.73 (17)C11B—O3B—C15B116.49 (18)
C2A—C1A—S1A112.9 (2)C2B—C1B—S1B112.52 (18)
C2A—C1A—H1AA123.5C2B—C1B—H1BA123.7
S1A—C1A—H1AA123.5S1B—C1B—H1BA123.7
C1A—C2A—C3A113.4 (2)C1B—C2B—C3B112.2 (2)
C1A—C2A—H2AA123.3C1B—C2B—H2BA123.9
C3A—C2A—H2AA123.3C3B—C2B—H2BA123.9
C4A—C3A—C2A110.4 (2)C4B—C3B—C2B113.1 (2)
C4A—C3A—H3AA124.8C4B—C3B—H3BA123.5
C2A—C3A—H3AA124.8C2B—C3B—H3BA123.5
C3A—C4A—C5A130.5 (2)C3B—C4B—C5B130.2 (2)
C3A—C4A—S1A111.49 (18)C3B—C4B—S1B110.32 (17)
C5A—C4A—S1A118.01 (16)C5B—C4B—S1B119.42 (17)
O1A—C5A—C4A120.2 (2)O1B—C5B—C4B120.7 (2)
O1A—C5A—C6A121.6 (2)O1B—C5B—C6B122.0 (2)
C4A—C5A—C6A118.2 (2)C4B—C5B—C6B117.2 (2)
C7A—C6A—C5A119.8 (2)C7B—C6B—C5B121.2 (2)
C7A—C6A—H6AA120.1C7B—C6B—H6BA119.4
C5A—C6A—H6AA120.1C5B—C6B—H6BA119.4
C6A—C7A—C8A128.6 (2)C6B—C7B—C8B128.1 (2)
C6A—C7A—H7AA115.7C6B—C7B—H7BA116.0
C8A—C7A—H7AA115.7C8B—C7B—H7BA116.0
C9A—C8A—C13A119.0 (2)C9B—C8B—C13B118.4 (2)
C9A—C8A—C7A118.3 (2)C9B—C8B—C7B118.9 (2)
C13A—C8A—C7A122.7 (2)C13B—C8B—C7B122.7 (2)
C10A—C9A—C8A121.1 (2)C8B—C9B—C10B121.4 (2)
C10A—C9A—H9AA119.5C8B—C9B—H9BA119.3
C8A—C9A—H9AA119.5C10B—C9B—H9BA119.3
C11A—C10A—C9A119.8 (2)C11B—C10B—C9B119.7 (2)
C11A—C10A—H10A120.1C11B—C10B—H10B120.1
C9A—C10A—H10A120.1C9B—C10B—H10B120.1
O3A—C11A—C10A124.9 (2)O3B—C11B—C10B125.0 (2)
O3A—C11A—C12A114.88 (19)O3B—C11B—C12B115.24 (19)
C10A—C11A—C12A120.2 (2)C10B—C11B—C12B119.7 (2)
O2A—C12A—C13A125.7 (2)O2B—C12B—C13B124.9 (2)
O2A—C12A—C11A114.77 (19)O2B—C12B—C11B114.97 (19)
C13A—C12A—C11A119.53 (19)C13B—C12B—C11B120.2 (2)
C12A—C13A—C8A120.4 (2)C12B—C13B—C8B120.6 (2)
C12A—C13A—H13A119.8C12B—C13B—H13B119.7
C8A—C13A—H13A119.8C8B—C13B—H13B119.7
O2A—C14A—H14A109.5O2B—C14B—H14D109.5
O2A—C14A—H14B109.5O2B—C14B—H14E109.5
H14A—C14A—H14B109.5H14D—C14B—H14E109.5
O2A—C14A—H14C109.5O2B—C14B—H14F109.5
H14A—C14A—H14C109.5H14D—C14B—H14F109.5
H14B—C14A—H14C109.5H14E—C14B—H14F109.5
O3A—C15A—H15A109.5O3B—C15B—H15D109.5
O3A—C15A—H15B109.5O3B—C15B—H15E109.5
H15A—C15A—H15B109.5H15D—C15B—H15E109.5
O3A—C15A—H15C109.5O3B—C15B—H15F109.5
H15A—C15A—H15C109.5H15D—C15B—H15F109.5
H15B—C15A—H15C109.5H15E—C15B—H15F109.5
C4A—S1A—C1A—C2A0.2 (2)C4B—S1B—C1B—C2B0.18 (19)
S1A—C1A—C2A—C3A0.3 (3)S1B—C1B—C2B—C3B0.5 (3)
C1A—C2A—C3A—C4A0.3 (3)C1B—C2B—C3B—C4B1.1 (3)
C2A—C3A—C4A—C5A177.2 (2)C2B—C3B—C4B—C5B177.3 (2)
C2A—C3A—C4A—S1A0.1 (2)C2B—C3B—C4B—S1B1.2 (2)
C1A—S1A—C4A—C3A0.04 (18)C1B—S1B—C4B—C3B0.78 (17)
C1A—S1A—C4A—C5A177.78 (18)C1B—S1B—C4B—C5B177.88 (17)
C3A—C4A—C5A—O1A180.0 (2)C3B—C4B—C5B—O1B178.9 (2)
S1A—C4A—C5A—O1A2.8 (3)S1B—C4B—C5B—O1B0.6 (3)
C3A—C4A—C5A—C6A0.8 (3)C3B—C4B—C5B—C6B0.5 (3)
S1A—C4A—C5A—C6A176.47 (16)S1B—C4B—C5B—C6B178.83 (15)
O1A—C5A—C6A—C7A2.0 (3)O1B—C5B—C6B—C7B4.4 (3)
C4A—C5A—C6A—C7A177.2 (2)C4B—C5B—C6B—C7B175.0 (2)
C5A—C6A—C7A—C8A179.6 (2)C5B—C6B—C7B—C8B178.5 (2)
C6A—C7A—C8A—C9A177.7 (2)C6B—C7B—C8B—C9B179.7 (2)
C6A—C7A—C8A—C13A0.7 (4)C6B—C7B—C8B—C13B0.8 (4)
C13A—C8A—C9A—C10A1.7 (3)C13B—C8B—C9B—C10B1.1 (3)
C7A—C8A—C9A—C10A176.7 (2)C7B—C8B—C9B—C10B177.9 (2)
C8A—C9A—C10A—C11A0.5 (4)C8B—C9B—C10B—C11B0.2 (3)
C15A—O3A—C11A—C10A1.0 (3)C15B—O3B—C11B—C10B3.4 (3)
C15A—O3A—C11A—C12A178.46 (19)C15B—O3B—C11B—C12B177.40 (19)
C9A—C10A—C11A—O3A178.4 (2)C9B—C10B—C11B—O3B178.4 (2)
C9A—C10A—C11A—C12A1.0 (3)C9B—C10B—C11B—C12B0.8 (3)
C14A—O2A—C12A—C13A7.8 (3)C14B—O2B—C12B—C13B1.0 (3)
C14A—O2A—C12A—C11A172.71 (19)C14B—O2B—C12B—C11B178.52 (19)
O3A—C11A—C12A—O2A2.1 (3)O3B—C11B—C12B—O2B1.3 (3)
C10A—C11A—C12A—O2A178.4 (2)C10B—C11B—C12B—O2B179.50 (19)
O3A—C11A—C12A—C13A178.34 (19)O3B—C11B—C12B—C13B178.29 (18)
C10A—C11A—C12A—C13A1.1 (3)C10B—C11B—C12B—C13B1.0 (3)
O2A—C12A—C13A—C8A179.7 (2)O2B—C12B—C13B—C8B179.62 (19)
C11A—C12A—C13A—C8A0.2 (3)C11B—C12B—C13B—C8B0.1 (3)
C9A—C8A—C13A—C12A1.6 (3)C9B—C8B—C13B—C12B0.9 (3)
C7A—C8A—C13A—C12A176.8 (2)C7B—C8B—C13B—C12B178.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7A—H7AA···O1A0.932.432.792 (3)103
C1B—H1BA···O1Ai0.932.363.261 (3)162
C7B—H7BA···O1B0.932.472.816 (3)102
C14B—H14F···O1Bii0.962.533.401 (3)151
C15A—H15A···Cg1iii0.962.923.616 (3)130
C10A—H10A···Cg3iv0.932.843.636 (3)144
C3A—H3AA···Cg40.932.793.370 (3)122
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z+1; (iii) x3/2, y+1/2, z3/2; (iv) x+1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC15H14O3S
Mr274.32
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)12.1509 (3), 14.3118 (3), 16.3692 (4)
β (°) 106.570 (2)
V3)2728.41 (11)
Z8
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.60 × 0.17 × 0.11
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.871, 0.974
No. of measured, independent and
observed [I > 2σ(I)] reflections
31879, 7997, 4723
Rint0.074
(sin θ/λ)max1)0.705
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.158, 1.07
No. of reflections7997
No. of parameters347
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.46, 0.44

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7A—H7AA···O1A0.932.432.792 (3)103
C1B—H1BA···O1Ai0.932.363.261 (3)162
C7B—H7BA···O1B0.932.472.816 (3)102
C14B—H14F···O1Bii0.962.533.401 (3)151
C15A—H15A···Cg1iii0.962.923.616 (3)130
C10A—H10A···Cg3iv0.932.843.636 (3)144
C3A—H3AA···Cg40.932.793.370 (3)122
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z+1; (iii) x3/2, y+1/2, z3/2; (iv) x+1/2, y+1/2, z+1/2.
 

Footnotes

Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India

Acknowledgements

FHK and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks the Universiti Sains Malaysia for a post-doctoral research fellowship.

References

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First citationPatil, P. S., Teh, J. B.-J., Fun, H.-K., Razak, I. A. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o896–o898.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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