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organic compounds
(E)-1-(2-Thienyl)-3-(2,4,5-trimethoxyphenyl)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
In the title molecule, C16H16O4S, the enone fragment, thiophene ring and benzene ring are individually essentially planar. The thiophene ring is disordered over two sites, corresponding to a rotation of approximately 180° about the single C—C bond to which it is attached. The approximate ratio of occupancies for the major and minor components is 0.872 (2):0.128 (2). The major component of the thiophene ring and the benzene ring are twisted from each other by 13.92 (19)°. An intramolecular C—H⋯O hydrogen bond generates an S(5)S(5) ring motif. The is stabilized by intermolecular C—H⋯O hydrogen-bonding interactions. In addition, a π–π stacking interaction, with a centroid–centroid distance of 3.852 (2) Å, and short S⋯O [2.9378 (12) Å] and O⋯O [2.5811 (16) Å] contacts are observed.
Related literature
For related literature, see: Chantrapromma et al. (2005, 2006
); Fun et al. (2006
); Patil, Fun et al. (2007
); Patil, Dharmaprakash et al.(2007
). For bond-length data, see: Allen et al. (1987
); Patil et al. (2006
). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2005); cell APEX2; data reduction: SAINT (Bruker, 2005
); program(s) used to solve structure: SHELXTL (Sheldrick, 2008
); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003
).
Supporting information
10.1107/S1600536808021375/lh2658sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808021375/lh2658Isup2.hkl
2,4,5-trimethoxybenzaldehyde (0.01 mol, 1.96 g m) in ethanol (30 ml) was mixed with 2-acetylthiophene (0.01 mol, 1.07 ml) in 30 ml ethanol and the mixture was treated with 10 ml of 10% sodium hydroxide solution and stirred at room temperature for 8 h. The precipitate obtained was poured into ice-cold water (500 ml) and left to stand for 5 h. The resulting crude solid was filtered, dried and recrystallized from N, N-dimethylformamide (DMF) by slow evaporation.
H atoms were positioned geometrically [C—H = 0.93Å; and CH3=0.96 Å] and refined using a riding model, with Uiso(H) = 1.2Ueq(C) and 1.5eq(Cmethyl). A rotating group model was used for the methyl groups. The ratio of the refined occupancies for the major and minor components of the disordered thiophene ring is 0.872 (2):0.128 (2). Similarity and rigid-bond restraints were applied to the disordered atoms.
Data collection: APEX2 (Bruker, 2005); cell
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).C16H16O4S | F(000) = 640 |
Mr = 304.35 | Dx = 1.401 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4291 reflections |
a = 7.5391 (1) Å | θ = 2.7–28.4° |
b = 7.9225 (1) Å | µ = 0.24 mm−1 |
c = 24.3399 (3) Å | T = 100 K |
β = 97.021 (1)° | Block, yellow |
V = 1442.88 (3) Å3 | 0.25 × 0.22 × 0.14 mm |
Z = 4 |
Bruker SMART APEXII CCD area-detector diffractometer | 4256 independent reflections |
Radiation source: fine-focus sealed tube | 3174 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.063 |
ϕ and ω scans | θmax = 30.1°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −10→10 |
Tmin = 0.942, Tmax = 0.967 | k = −11→10 |
33027 measured reflections | l = −34→34 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0532P)2 + 0.4695P] where P = (Fo2 + 2Fc2)/3 |
4256 reflections | (Δ/σ)max < 0.001 |
211 parameters | Δρmax = 0.41 e Å−3 |
120 restraints | Δρmin = −0.22 e Å−3 |
C16H16O4S | V = 1442.88 (3) Å3 |
Mr = 304.35 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.5391 (1) Å | µ = 0.24 mm−1 |
b = 7.9225 (1) Å | T = 100 K |
c = 24.3399 (3) Å | 0.25 × 0.22 × 0.14 mm |
β = 97.021 (1)° |
Bruker SMART APEXII CCD area-detector diffractometer | 4256 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 3174 reflections with I > 2σ(I) |
Tmin = 0.942, Tmax = 0.967 | Rint = 0.063 |
33027 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 120 restraints |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.41 e Å−3 |
4256 reflections | Δρmin = −0.22 e Å−3 |
211 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.21432 (18) | −0.07151 (14) | 0.09237 (4) | 0.0317 (3) | |
O2 | 0.17726 (15) | 0.05965 (14) | −0.21790 (4) | 0.0241 (2) | |
O3 | 0.32216 (15) | −0.21704 (14) | −0.24632 (4) | 0.0245 (2) | |
O4 | 0.38751 (16) | −0.41134 (14) | −0.05568 (4) | 0.0256 (3) | |
C4 | 0.1783 (2) | 0.22121 (18) | 0.08330 (6) | 0.0207 (3) | |
S1 | 0.17822 (8) | 0.24407 (6) | 0.153399 (18) | 0.02221 (15) | 0.870 (2) |
C1 | 0.1475 (5) | 0.4570 (4) | 0.14728 (11) | 0.0232 (6) | 0.870 (2) |
H1A | 0.1413 | 0.5286 | 0.1773 | 0.028* | 0.870 (2) |
C2 | 0.1330 (9) | 0.5112 (4) | 0.09346 (15) | 0.0270 (8) | 0.870 (2) |
H2A | 0.1119 | 0.6223 | 0.0822 | 0.032* | 0.870 (2) |
C3 | 0.1544 (10) | 0.3750 (7) | 0.05759 (18) | 0.0335 (12) | 0.870 (2) |
H3A | 0.1526 | 0.3883 | 0.0196 | 0.040* | 0.870 (2) |
S1X | 0.1377 (15) | 0.3871 (9) | 0.0437 (3) | 0.0239 (13) | 0.130 (2) |
C1X | 0.145 (7) | 0.511 (3) | 0.1014 (8) | 0.036 (8)* | 0.130 (2) |
H1XA | 0.1481 | 0.6281 | 0.1003 | 0.043* | 0.130 (2) |
C2X | 0.147 (4) | 0.421 (2) | 0.1494 (9) | 0.027 (6)* | 0.130 (2) |
H2XA | 0.1296 | 0.4635 | 0.1839 | 0.032* | 0.130 (2) |
C3X | 0.180 (3) | 0.253 (2) | 0.1369 (6) | 0.0335 (12) | 0.130 (2) |
H3XA | 0.2008 | 0.1699 | 0.1640 | 0.040* | 0.130 (2) |
C5 | 0.2048 (2) | 0.05105 (19) | 0.06134 (6) | 0.0227 (3) | |
C6 | 0.2186 (2) | 0.03664 (19) | 0.00174 (6) | 0.0237 (3) | |
H6A | 0.1975 | 0.1315 | −0.0206 | 0.028* | |
C7 | 0.2608 (2) | −0.10914 (19) | −0.02109 (6) | 0.0224 (3) | |
H7A | 0.2816 | −0.2009 | 0.0027 | 0.027* | |
C8 | 0.2776 (2) | −0.13959 (18) | −0.07931 (6) | 0.0203 (3) | |
C9 | 0.3410 (2) | −0.29444 (19) | −0.09632 (6) | 0.0205 (3) | |
C10 | 0.3580 (2) | −0.32485 (19) | −0.15198 (6) | 0.0210 (3) | |
H10A | 0.4022 | −0.4277 | −0.1627 | 0.025* | |
C11 | 0.3088 (2) | −0.20143 (19) | −0.19118 (6) | 0.0200 (3) | |
C12 | 0.2371 (2) | −0.04789 (19) | −0.17534 (6) | 0.0204 (3) | |
C13 | 0.2256 (2) | −0.01779 (19) | −0.12019 (6) | 0.0211 (3) | |
H13A | 0.1823 | 0.0857 | −0.1097 | 0.025* | |
C14 | 0.0920 (2) | 0.2100 (2) | −0.20310 (6) | 0.0280 (4) | |
H14A | 0.0559 | 0.2753 | −0.2358 | 0.042* | |
H14B | 0.1736 | 0.2746 | −0.1780 | 0.042* | |
H14C | −0.0113 | 0.1815 | −0.1855 | 0.042* | |
C15 | 0.3832 (2) | −0.3757 (2) | −0.26506 (7) | 0.0305 (4) | |
H15A | 0.3869 | −0.3710 | −0.3043 | 0.046* | |
H15B | 0.3028 | −0.4635 | −0.2568 | 0.046* | |
H15C | 0.5007 | −0.3988 | −0.2467 | 0.046* | |
C16 | 0.4083 (2) | −0.5814 (2) | −0.07198 (7) | 0.0278 (3) | |
H16B | 0.4405 | −0.6498 | −0.0397 | 0.042* | |
H16C | 0.5006 | −0.5879 | −0.0958 | 0.042* | |
H16D | 0.2979 | −0.6215 | −0.0914 | 0.042* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0575 (8) | 0.0197 (6) | 0.0187 (5) | 0.0009 (5) | 0.0076 (5) | 0.0019 (4) |
O2 | 0.0354 (6) | 0.0222 (5) | 0.0150 (5) | 0.0045 (5) | 0.0046 (4) | 0.0008 (4) |
O3 | 0.0346 (6) | 0.0249 (6) | 0.0151 (5) | 0.0023 (5) | 0.0077 (4) | −0.0036 (4) |
O4 | 0.0389 (6) | 0.0205 (5) | 0.0167 (5) | 0.0049 (5) | 0.0009 (4) | −0.0005 (4) |
C4 | 0.0270 (7) | 0.0213 (7) | 0.0144 (6) | −0.0020 (6) | 0.0050 (5) | −0.0017 (5) |
S1 | 0.0312 (3) | 0.0219 (2) | 0.0139 (2) | −0.00063 (17) | 0.0044 (2) | −0.00192 (18) |
C1 | 0.0330 (13) | 0.0168 (12) | 0.0206 (11) | 0.0017 (12) | 0.0061 (7) | −0.0042 (9) |
C2 | 0.0443 (19) | 0.0168 (11) | 0.0206 (11) | −0.0016 (8) | 0.0072 (15) | −0.0015 (7) |
C3 | 0.0466 (19) | 0.0352 (17) | 0.020 (2) | −0.0016 (12) | 0.0106 (17) | −0.0004 (13) |
S1X | 0.041 (3) | 0.0111 (18) | 0.022 (3) | −0.0021 (16) | 0.014 (2) | −0.0060 (17) |
C3X | 0.0466 (19) | 0.0352 (17) | 0.020 (2) | −0.0016 (12) | 0.0106 (17) | −0.0004 (13) |
C5 | 0.0312 (8) | 0.0208 (7) | 0.0167 (7) | −0.0011 (6) | 0.0048 (6) | −0.0011 (5) |
C6 | 0.0353 (8) | 0.0201 (7) | 0.0164 (7) | −0.0018 (6) | 0.0058 (6) | 0.0006 (5) |
C7 | 0.0277 (8) | 0.0234 (7) | 0.0163 (6) | −0.0010 (6) | 0.0025 (6) | −0.0002 (5) |
C8 | 0.0269 (7) | 0.0190 (7) | 0.0153 (6) | −0.0026 (6) | 0.0042 (5) | −0.0023 (5) |
C9 | 0.0242 (7) | 0.0203 (7) | 0.0166 (7) | −0.0006 (6) | 0.0005 (5) | −0.0002 (5) |
C10 | 0.0256 (7) | 0.0207 (7) | 0.0172 (7) | 0.0005 (6) | 0.0042 (5) | −0.0033 (5) |
C11 | 0.0228 (7) | 0.0234 (7) | 0.0140 (6) | −0.0023 (6) | 0.0037 (5) | −0.0021 (5) |
C12 | 0.0246 (7) | 0.0207 (7) | 0.0163 (6) | −0.0017 (6) | 0.0039 (5) | 0.0006 (5) |
C13 | 0.0286 (8) | 0.0184 (7) | 0.0169 (7) | −0.0009 (6) | 0.0047 (6) | −0.0022 (5) |
C14 | 0.0395 (9) | 0.0243 (8) | 0.0201 (7) | 0.0073 (7) | 0.0030 (6) | 0.0005 (6) |
C15 | 0.0429 (10) | 0.0298 (9) | 0.0196 (7) | 0.0075 (7) | 0.0064 (7) | −0.0071 (6) |
C16 | 0.0396 (9) | 0.0207 (7) | 0.0221 (7) | 0.0019 (7) | −0.0002 (6) | −0.0007 (6) |
O1—C5 | 1.2268 (18) | C3X—H3XA | 0.9300 |
O2—C12 | 1.3741 (17) | C5—C6 | 1.472 (2) |
O2—C14 | 1.4206 (19) | C6—C7 | 1.337 (2) |
O3—C11 | 1.3637 (17) | C6—H6A | 0.9300 |
O3—C15 | 1.4319 (19) | C7—C8 | 1.4582 (19) |
O4—C9 | 1.3692 (17) | C7—H7A | 0.9300 |
O4—C16 | 1.4182 (18) | C8—C9 | 1.398 (2) |
C4—C3X | 1.328 (13) | C8—C13 | 1.407 (2) |
C4—C3 | 1.371 (5) | C9—C10 | 1.3972 (19) |
C4—C5 | 1.473 (2) | C10—C11 | 1.385 (2) |
C4—S1X | 1.636 (7) | C10—H10A | 0.9300 |
C4—S1 | 1.7158 (15) | C11—C12 | 1.404 (2) |
S1—C1 | 1.707 (3) | C12—C13 | 1.376 (2) |
C1—C2 | 1.370 (4) | C13—H13A | 0.9300 |
C1—H1A | 0.9300 | C14—H14A | 0.9600 |
C2—C3 | 1.410 (6) | C14—H14B | 0.9600 |
C2—H2A | 0.9300 | C14—H14C | 0.9600 |
C3—H3A | 0.9300 | C15—H15A | 0.9600 |
S1X—C1X | 1.708 (18) | C15—H15B | 0.9600 |
C1X—C2X | 1.368 (17) | C15—H15C | 0.9600 |
C1X—H1XA | 0.9300 | C16—H16B | 0.9600 |
C2X—C3X | 1.391 (17) | C16—H16C | 0.9600 |
C2X—H2XA | 0.9300 | C16—H16D | 0.9600 |
C12—O2—C14 | 116.47 (11) | C6—C7—H7A | 116.6 |
C11—O3—C15 | 117.29 (12) | C8—C7—H7A | 116.6 |
C9—O4—C16 | 117.89 (11) | C9—C8—C13 | 117.93 (13) |
C3X—C4—C3 | 105.4 (8) | C9—C8—C7 | 120.43 (13) |
C3X—C4—C5 | 123.0 (8) | C13—C8—C7 | 121.61 (13) |
C3—C4—C5 | 131.6 (2) | O4—C9—C10 | 122.55 (13) |
C3X—C4—S1X | 113.9 (8) | O4—C9—C8 | 116.52 (12) |
C5—C4—S1X | 123.0 (3) | C10—C9—C8 | 120.92 (13) |
C3—C4—S1 | 110.1 (2) | C11—C10—C9 | 119.84 (14) |
C5—C4—S1 | 118.30 (11) | C11—C10—H10A | 120.1 |
S1X—C4—S1 | 118.6 (3) | C9—C10—H10A | 120.1 |
C1—S1—C4 | 91.96 (10) | O3—C11—C10 | 124.62 (13) |
C2—C1—S1 | 112.8 (2) | O3—C11—C12 | 115.23 (13) |
C2—C1—H1A | 123.6 | C10—C11—C12 | 120.15 (13) |
S1—C1—H1A | 123.6 | O2—C12—C13 | 125.01 (13) |
C1—C2—C3 | 110.5 (3) | O2—C12—C11 | 115.59 (12) |
C1—C2—H2A | 124.7 | C13—C12—C11 | 119.36 (13) |
C3—C2—H2A | 124.7 | C12—C13—C8 | 121.70 (14) |
C4—C3—C2 | 114.6 (3) | C12—C13—H13A | 119.2 |
C4—C3—H3A | 122.7 | C8—C13—H13A | 119.2 |
C2—C3—H3A | 122.7 | O2—C14—H14A | 109.5 |
C4—S1X—C1X | 89.5 (9) | O2—C14—H14B | 109.5 |
C2X—C1X—S1X | 113.4 (16) | H14A—C14—H14B | 109.5 |
C2X—C1X—H1XA | 123.3 | O2—C14—H14C | 109.5 |
S1X—C1X—H1XA | 123.3 | H14A—C14—H14C | 109.5 |
C1X—C2X—C3X | 107.3 (17) | H14B—C14—H14C | 109.5 |
C1X—C2X—H2XA | 126.4 | O3—C15—H15A | 109.5 |
C3X—C2X—H2XA | 126.4 | O3—C15—H15B | 109.5 |
C4—C3X—C2X | 114.5 (14) | H15A—C15—H15B | 109.5 |
C4—C3X—H3XA | 122.8 | O3—C15—H15C | 109.5 |
C2X—C3X—H3XA | 122.8 | H15A—C15—H15C | 109.5 |
O1—C5—C6 | 122.66 (14) | H15B—C15—H15C | 109.5 |
O1—C5—C4 | 120.09 (13) | O4—C16—H16B | 109.5 |
C6—C5—C4 | 117.25 (13) | O4—C16—H16C | 109.5 |
C7—C6—C5 | 121.74 (14) | H16B—C16—H16C | 109.5 |
C7—C6—H6A | 119.1 | O4—C16—H16D | 109.5 |
C5—C6—H6A | 119.1 | H16B—C16—H16D | 109.5 |
C6—C7—C8 | 126.89 (14) | H16C—C16—H16D | 109.5 |
C3X—C4—S1—C1 | 13 (12) | S1—C4—C5—C6 | −175.26 (11) |
C3—C4—S1—C1 | −0.2 (4) | O1—C5—C6—C7 | −7.0 (3) |
C5—C4—S1—C1 | 178.97 (18) | C4—C5—C6—C7 | 173.08 (15) |
S1X—C4—S1—C1 | −4.5 (5) | C5—C6—C7—C8 | 179.63 (14) |
C4—S1—C1—C2 | 1.5 (4) | C6—C7—C8—C9 | 173.21 (16) |
S1—C1—C2—C3 | −2.2 (7) | C6—C7—C8—C13 | −8.9 (3) |
C3X—C4—C3—C2 | −2.2 (11) | C16—O4—C9—C10 | −16.9 (2) |
C5—C4—C3—C2 | 179.9 (4) | C16—O4—C9—C8 | 164.24 (14) |
S1X—C4—C3—C2 | 155 (5) | C13—C8—C9—O4 | −178.88 (13) |
S1—C4—C3—C2 | −1.0 (7) | C7—C8—C9—O4 | −0.9 (2) |
C1—C2—C3—C4 | 2.1 (8) | C13—C8—C9—C10 | 2.2 (2) |
C3X—C4—S1X—C1X | 6 (2) | C7—C8—C9—C10 | −179.86 (14) |
C3—C4—S1X—C1X | −18 (4) | O4—C9—C10—C11 | −179.94 (14) |
C5—C4—S1X—C1X | −175.8 (18) | C8—C9—C10—C11 | −1.1 (2) |
S1—C4—S1X—C1X | 7.8 (19) | C15—O3—C11—C10 | 3.3 (2) |
C4—S1X—C1X—C2X | −11 (4) | C15—O3—C11—C12 | −175.89 (14) |
S1X—C1X—C2X—C3X | 12 (5) | C9—C10—C11—O3 | 179.05 (13) |
C3—C4—C3X—C2X | 4 (2) | C9—C10—C11—C12 | −1.8 (2) |
C5—C4—C3X—C2X | −178.2 (17) | C14—O2—C12—C13 | −2.3 (2) |
S1X—C4—C3X—C2X | 0 (3) | C14—O2—C12—C11 | 175.38 (14) |
S1—C4—C3X—C2X | −163 (13) | O3—C11—C12—O2 | 4.99 (19) |
C1X—C2X—C3X—C4 | −8 (4) | C10—C11—C12—O2 | −174.20 (13) |
C3X—C4—C5—O1 | 6.3 (12) | O3—C11—C12—C13 | −177.23 (13) |
C3—C4—C5—O1 | −176.2 (4) | C10—C11—C12—C13 | 3.6 (2) |
S1X—C4—C5—O1 | −171.6 (5) | O2—C12—C13—C8 | 175.11 (14) |
S1—C4—C5—O1 | 4.8 (2) | C11—C12—C13—C8 | −2.4 (2) |
C3X—C4—C5—C6 | −173.8 (12) | C9—C8—C13—C12 | −0.4 (2) |
C3—C4—C5—C6 | 3.7 (5) | C7—C8—C13—C12 | −178.33 (14) |
S1X—C4—C5—C6 | 8.3 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···O1i | 0.93 | 2.55 | 3.363 (4) | 146 |
C7—H7A···O1 | 0.93 | 2.52 | 2.8416 (18) | 101 |
C7—H7A···O4 | 0.93 | 2.39 | 2.7477 (19) | 103 |
C16—H16B···O4ii | 0.96 | 2.56 | 3.2952 (19) | 133 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y−1, −z. |
Experimental details
Crystal data | |
Chemical formula | C16H16O4S |
Mr | 304.35 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 7.5391 (1), 7.9225 (1), 24.3399 (3) |
β (°) | 97.021 (1) |
V (Å3) | 1442.88 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.25 × 0.22 × 0.14 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.942, 0.967 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 33027, 4256, 3174 |
Rint | 0.063 |
(sin θ/λ)max (Å−1) | 0.706 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.120, 1.07 |
No. of reflections | 4256 |
No. of parameters | 211 |
No. of restraints | 120 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.41, −0.22 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···O1i | 0.93 | 2.55 | 3.363 (4) | 146 |
C7—H7A···O1 | 0.93 | 2.52 | 2.8416 (18) | 101 |
C7—H7A···O4 | 0.93 | 2.39 | 2.7477 (19) | 103 |
C16—H16B···O4ii | 0.96 | 2.56 | 3.2952 (19) | 133 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y−1, −z. |
Footnotes
‡Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India.
Acknowledgements
HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a post-doctoral research fellowship. This work was supported by the Department of Science and Technology (DST), Government of India (grant No. SR/S2/LOP-17/2006).
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The title compound (I) has been synthesized as part of our crystallographic studies on nonlinear optical materials (Chantrapromma et al., 2005, 2006; Fun et al., 2006; Patil, Fun et al., 2007; Patil, Dharmaprakash et al., 2007). We report herein the crystal structure of the title compound, (I).
In the title molecular structure (I), the thiophene ring is disordered over two sites (atoms of the minor occupancy component are labelled with the suffix X), corresponding to a rotation of approximately 180° about the C4—C5 bond. The bond lengths and bond angles are found to have normal values (Allen et al., 1987) and agree with a related structure (Patil et al., 2006) with the execption of some parameters of the thiophene ring, which are probably a consequence of the disorder. The benzene and thiophene rings are individually planar, with maximum deviations of 0.019 (2) Å for atom C12 and -0.074 (2)Å for atom C1X. The molecule is twisted about the C7—C8 bond with a dihedral angle of 13.93 (19)° between the benzene ring and S1/C1—C4 [15.9 (19)° for S1X/C1X—C3X].
Intramolecular hydrogen bond C—H···O generates ring motif S(5)S(5) (Bernstein et al., 1995). The crystal packing is stabilized by intra and intermolecular C—H···O interactions. π—π interactions between the S1/C1—C4 (centroid Cg1) and C8—C13 (centroid Cg3) rings [Cg1···Cg3i=3.852 (2) Å] [symmetry code: (i) -x,-y,-z] together with S···O=2.9378 (12)Å and O···O=2.5811 (16)Å short contacts are observed.