organic compounds
(2E)-1-(2-Methyl-4-phenylquinolin-3-yl)-3-(3-methylthiophen-2-yl)prop-2-en-1-one
aDepartment of Chemistry, BITS, Pilani–K. K. Birla Goa Campus, Goa 403 726, India, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: edward.tiekink@gmail.com
In the title compound, C24H19NOS, the quinoline residue (r.m.s. deviation = 0.018 Å) is essentially orthogonal to both the phenyl [dihedral angle = 88.95 (8)°] and 2-thienyl [81.98 (9)°] rings. The carbonyl O atom lies to one side of the quinoline plane, the carbonyl C atom is almost coplanar and the remaining atoms of the chalcone residue lies to the other side, so that overall the molecule has an L-shape. The conformation about the ethylene bond [1.340 (2) Å] is E. In the crystal, a supramolecular chain with the shape of a square rod aligned along the b-axis direction is sustained by C—H⋯π interactions, the π-systems being the heterocyclic rings.
Related literature
For background details and the biological application of quinoline and quinoline et al. (2011); Prasath & Bhavana (2012); Kalanithi et al. (2012); Prasath et al. (2013). For the structure of the dimethyl-substituted quinolinyl compound without a methyl substituent on the 2-thienyl ring, see: Prasath et al. (2011).
see: JoshiExperimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Agilent, 2011); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536813004753/hb7043sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813004753/hb7043Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536813004753/hb7043Isup3.cml
A mixture of 3-acetyl-2-methyl-4-phenylquinoline (1.3 g, 0.005 M), 3-methylthiophene-2-carbaldehyde (630 mg, 0.005 M) and KOH (0.5 g) in distilled ethanol (50 ml) was stirred for 12 h at room temperature. The resulting mixture was neutralized with dilute acetic acid. The deposited solid was filtered, dried and purified by
using a 1:1 mixture of ethyl acetate and hexane. Re-crystallization was by slow evaporation of an acetone solution of (I), which yielded colourless prisms in 76% yield; M.pt: 453–455 K.The C-bound H atoms were geometrically placed (C—H = 0.95–0.96 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C).
Data collection: CrysAlis PRO (Agilent, 2011); cell
CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).C24H19NOS | Z = 2 |
Mr = 369.46 | F(000) = 388 |
Triclinic, P1 | Dx = 1.265 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.0815 (7) Å | Cell parameters from 2781 reflections |
b = 10.2956 (7) Å | θ = 3.1–27.5° |
c = 10.5403 (7) Å | µ = 0.18 mm−1 |
α = 71.013 (6)° | T = 295 K |
β = 78.697 (5)° | Prism, colourless |
γ = 70.412 (6)° | 0.40 × 0.20 × 0.10 mm |
V = 969.99 (11) Å3 |
Agilent SuperNova Dual diffractometer with an Atlas detector | 4473 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 3484 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.025 |
Detector resolution: 10.4041 pixels mm-1 | θmax = 27.6°, θmin = 3.1° |
ω scan | h = −12→13 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | k = −13→13 |
Tmin = 0.780, Tmax = 1.000 | l = −12→13 |
8430 measured reflections |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0573P)2 + 0.2365P] where P = (Fo2 + 2Fc2)/3 |
4473 reflections | (Δ/σ)max < 0.001 |
246 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
C24H19NOS | γ = 70.412 (6)° |
Mr = 369.46 | V = 969.99 (11) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.0815 (7) Å | Mo Kα radiation |
b = 10.2956 (7) Å | µ = 0.18 mm−1 |
c = 10.5403 (7) Å | T = 295 K |
α = 71.013 (6)° | 0.40 × 0.20 × 0.10 mm |
β = 78.697 (5)° |
Agilent SuperNova Dual diffractometer with an Atlas detector | 4473 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | 3484 reflections with I > 2σ(I) |
Tmin = 0.780, Tmax = 1.000 | Rint = 0.025 |
8430 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.28 e Å−3 |
4473 reflections | Δρmin = −0.26 e Å−3 |
246 parameters |
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 | ||
S1 | 0.33532 (6) | 0.72592 (6) | 0.97283 (5) | 0.05153 (17) | |
O1 | 0.33453 (18) | 0.20079 (15) | 1.00072 (14) | 0.0629 (4) | |
N1 | 0.08222 (15) | 0.34043 (16) | 0.65204 (16) | 0.0454 (4) | |
C1 | 0.18240 (18) | 0.31032 (18) | 0.54916 (17) | 0.0399 (4) | |
C2 | 0.1367 (2) | 0.3073 (2) | 0.4323 (2) | 0.0527 (5) | |
H2 | 0.0406 | 0.3285 | 0.4262 | 0.063* | |
C3 | 0.2316 (3) | 0.2738 (2) | 0.3286 (2) | 0.0602 (5) | |
H3 | 0.2002 | 0.2718 | 0.2522 | 0.072* | |
C4 | 0.3757 (2) | 0.2425 (3) | 0.3361 (2) | 0.0608 (6) | |
H4 | 0.4397 | 0.2196 | 0.2645 | 0.073* | |
C5 | 0.4241 (2) | 0.2449 (2) | 0.44696 (19) | 0.0511 (5) | |
H5 | 0.5208 | 0.2241 | 0.4502 | 0.061* | |
C6 | 0.32869 (18) | 0.27881 (17) | 0.55698 (17) | 0.0379 (4) | |
C7 | 0.37112 (17) | 0.28190 (17) | 0.67702 (17) | 0.0363 (4) | |
C8 | 0.26889 (17) | 0.31240 (17) | 0.77857 (17) | 0.0367 (4) | |
C9 | 0.12435 (18) | 0.33970 (19) | 0.76224 (19) | 0.0432 (4) | |
C10 | 0.0110 (2) | 0.3675 (3) | 0.8747 (2) | 0.0672 (6) | |
H10A | −0.0802 | 0.3905 | 0.8445 | 0.101* | |
H10B | 0.0164 | 0.4466 | 0.9008 | 0.101* | |
H10C | 0.0244 | 0.2833 | 0.9505 | 0.101* | |
C11 | 0.52458 (17) | 0.24958 (18) | 0.69071 (16) | 0.0377 (4) | |
C12 | 0.6053 (2) | 0.1100 (2) | 0.7428 (2) | 0.0514 (5) | |
H12 | 0.5634 | 0.0361 | 0.7717 | 0.062* | |
C13 | 0.7480 (2) | 0.0793 (2) | 0.7525 (2) | 0.0561 (5) | |
H13 | 0.8016 | −0.0151 | 0.7874 | 0.067* | |
C14 | 0.8112 (2) | 0.1878 (2) | 0.71062 (19) | 0.0520 (5) | |
H14 | 0.9074 | 0.1666 | 0.7162 | 0.062* | |
C15 | 0.7321 (2) | 0.3266 (2) | 0.6608 (2) | 0.0526 (5) | |
H15 | 0.7745 | 0.4002 | 0.6334 | 0.063* | |
C16 | 0.5892 (2) | 0.3582 (2) | 0.65095 (19) | 0.0467 (4) | |
H16 | 0.5360 | 0.4531 | 0.6174 | 0.056* | |
C17 | 0.30768 (19) | 0.31202 (19) | 0.90990 (18) | 0.0415 (4) | |
C18 | 0.30830 (19) | 0.44686 (19) | 0.92575 (18) | 0.0416 (4) | |
H18 | 0.3353 | 0.4453 | 1.0059 | 0.050* | |
C19 | 0.27227 (18) | 0.57334 (18) | 0.83162 (17) | 0.0391 (4) | |
H19 | 0.2463 | 0.5721 | 0.7522 | 0.047* | |
C20 | 0.26953 (18) | 0.71087 (18) | 0.84036 (17) | 0.0385 (4) | |
C21 | 0.2191 (2) | 0.84246 (19) | 0.75107 (18) | 0.0454 (4) | |
C22 | 0.2355 (2) | 0.9534 (2) | 0.7922 (2) | 0.0590 (5) | |
H22 | 0.2071 | 1.0497 | 0.7435 | 0.071* | |
C23 | 0.2960 (3) | 0.9070 (2) | 0.9081 (2) | 0.0606 (6) | |
H23 | 0.3141 | 0.9670 | 0.9480 | 0.073* | |
C24 | 0.1539 (3) | 0.8692 (3) | 0.6258 (2) | 0.0666 (6) | |
H24A | 0.2032 | 0.7936 | 0.5843 | 0.100* | |
H24B | 0.1604 | 0.9595 | 0.5644 | 0.100* | |
H24C | 0.0563 | 0.8715 | 0.6484 | 0.100* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0653 (3) | 0.0586 (3) | 0.0420 (3) | −0.0270 (3) | −0.0072 (2) | −0.0187 (2) |
O1 | 0.0963 (12) | 0.0451 (8) | 0.0471 (8) | −0.0234 (8) | −0.0149 (8) | −0.0052 (6) |
N1 | 0.0385 (8) | 0.0491 (9) | 0.0537 (9) | −0.0144 (7) | −0.0028 (7) | −0.0203 (7) |
C1 | 0.0421 (9) | 0.0381 (9) | 0.0429 (9) | −0.0148 (7) | −0.0045 (7) | −0.0126 (7) |
C2 | 0.0524 (11) | 0.0573 (12) | 0.0557 (11) | −0.0191 (10) | −0.0130 (9) | −0.0178 (10) |
C3 | 0.0766 (15) | 0.0704 (14) | 0.0451 (11) | −0.0282 (12) | −0.0101 (10) | −0.0222 (10) |
C4 | 0.0661 (14) | 0.0750 (15) | 0.0488 (11) | −0.0261 (12) | 0.0074 (10) | −0.0290 (11) |
C5 | 0.0475 (10) | 0.0645 (12) | 0.0479 (10) | −0.0219 (10) | 0.0050 (9) | −0.0245 (9) |
C6 | 0.0401 (9) | 0.0364 (8) | 0.0404 (9) | −0.0156 (7) | −0.0011 (7) | −0.0120 (7) |
C7 | 0.0380 (8) | 0.0321 (8) | 0.0412 (9) | −0.0137 (7) | −0.0025 (7) | −0.0108 (7) |
C8 | 0.0396 (9) | 0.0345 (8) | 0.0392 (8) | −0.0135 (7) | −0.0007 (7) | −0.0135 (7) |
C9 | 0.0381 (9) | 0.0454 (10) | 0.0493 (10) | −0.0135 (8) | 0.0028 (8) | −0.0199 (8) |
C10 | 0.0439 (11) | 0.1004 (18) | 0.0656 (14) | −0.0208 (12) | 0.0099 (10) | −0.0432 (13) |
C11 | 0.0366 (9) | 0.0420 (9) | 0.0371 (8) | −0.0139 (7) | −0.0011 (7) | −0.0134 (7) |
C12 | 0.0469 (10) | 0.0448 (10) | 0.0613 (12) | −0.0176 (9) | −0.0012 (9) | −0.0114 (9) |
C13 | 0.0451 (11) | 0.0522 (12) | 0.0639 (13) | −0.0066 (9) | −0.0087 (9) | −0.0128 (10) |
C14 | 0.0379 (9) | 0.0735 (14) | 0.0508 (11) | −0.0182 (10) | −0.0040 (8) | −0.0239 (10) |
C15 | 0.0509 (11) | 0.0640 (13) | 0.0551 (11) | −0.0318 (10) | −0.0013 (9) | −0.0194 (10) |
C16 | 0.0476 (10) | 0.0449 (10) | 0.0523 (11) | −0.0189 (8) | −0.0074 (8) | −0.0129 (8) |
C17 | 0.0421 (9) | 0.0416 (9) | 0.0419 (9) | −0.0136 (8) | 0.0001 (7) | −0.0142 (8) |
C18 | 0.0449 (9) | 0.0446 (10) | 0.0395 (9) | −0.0130 (8) | −0.0047 (7) | −0.0171 (8) |
C19 | 0.0414 (9) | 0.0427 (9) | 0.0380 (9) | −0.0134 (8) | −0.0026 (7) | −0.0172 (7) |
C20 | 0.0397 (9) | 0.0426 (9) | 0.0374 (8) | −0.0139 (7) | 0.0003 (7) | −0.0170 (7) |
C21 | 0.0489 (10) | 0.0430 (10) | 0.0456 (10) | −0.0133 (8) | −0.0019 (8) | −0.0157 (8) |
C22 | 0.0767 (14) | 0.0408 (10) | 0.0626 (13) | −0.0196 (10) | −0.0046 (11) | −0.0173 (9) |
C23 | 0.0802 (15) | 0.0572 (12) | 0.0616 (13) | −0.0354 (12) | 0.0030 (11) | −0.0293 (11) |
C24 | 0.0771 (15) | 0.0589 (13) | 0.0609 (13) | −0.0090 (12) | −0.0250 (12) | −0.0138 (11) |
S1—C23 | 1.698 (2) | C11—C16 | 1.389 (2) |
S1—C20 | 1.7281 (17) | C12—C13 | 1.382 (3) |
O1—C17 | 1.217 (2) | C12—H12 | 0.9300 |
N1—C9 | 1.310 (2) | C13—C14 | 1.376 (3) |
N1—C1 | 1.368 (2) | C13—H13 | 0.9300 |
C1—C6 | 1.413 (2) | C14—C15 | 1.366 (3) |
C1—C2 | 1.410 (3) | C14—H14 | 0.9300 |
C2—C3 | 1.358 (3) | C15—C16 | 1.384 (3) |
C2—H2 | 0.9300 | C15—H15 | 0.9300 |
C3—C4 | 1.390 (3) | C16—H16 | 0.9300 |
C3—H3 | 0.9300 | C17—C18 | 1.453 (2) |
C4—C5 | 1.362 (3) | C18—C19 | 1.340 (2) |
C4—H4 | 0.9300 | C18—H18 | 0.9300 |
C5—C6 | 1.412 (2) | C19—C20 | 1.439 (2) |
C5—H5 | 0.9300 | C19—H19 | 0.9300 |
C6—C7 | 1.426 (2) | C20—C21 | 1.370 (3) |
C7—C8 | 1.370 (2) | C21—C22 | 1.413 (3) |
C7—C11 | 1.495 (2) | C21—C24 | 1.494 (3) |
C8—C9 | 1.423 (2) | C22—C23 | 1.345 (3) |
C8—C17 | 1.509 (2) | C22—H22 | 0.9300 |
C9—C10 | 1.505 (2) | C23—H23 | 0.9300 |
C10—H10A | 0.9600 | C24—H24A | 0.9600 |
C10—H10B | 0.9600 | C24—H24B | 0.9600 |
C10—H10C | 0.9600 | C24—H24C | 0.9600 |
C11—C12 | 1.381 (3) | ||
C23—S1—C20 | 91.61 (10) | C13—C12—H12 | 119.7 |
C9—N1—C1 | 118.32 (15) | C14—C13—C12 | 120.29 (19) |
N1—C1—C6 | 122.78 (16) | C14—C13—H13 | 119.9 |
N1—C1—C2 | 118.05 (16) | C12—C13—H13 | 119.9 |
C6—C1—C2 | 119.15 (16) | C15—C14—C13 | 119.83 (18) |
C3—C2—C1 | 120.68 (19) | C15—C14—H14 | 120.1 |
C3—C2—H2 | 119.7 | C13—C14—H14 | 120.1 |
C1—C2—H2 | 119.7 | C14—C15—C16 | 120.21 (17) |
C2—C3—C4 | 120.30 (19) | C14—C15—H15 | 119.9 |
C2—C3—H3 | 119.9 | C16—C15—H15 | 119.9 |
C4—C3—H3 | 119.9 | C15—C16—C11 | 120.58 (18) |
C5—C4—C3 | 120.85 (19) | C15—C16—H16 | 119.7 |
C5—C4—H4 | 119.6 | C11—C16—H16 | 119.7 |
C3—C4—H4 | 119.6 | O1—C17—C18 | 121.50 (17) |
C4—C5—C6 | 120.50 (18) | O1—C17—C8 | 119.87 (15) |
C4—C5—H5 | 119.8 | C18—C17—C8 | 118.60 (15) |
C6—C5—H5 | 119.8 | C19—C18—C17 | 123.79 (16) |
C1—C6—C5 | 118.52 (16) | C19—C18—H18 | 118.1 |
C1—C6—C7 | 117.62 (15) | C17—C18—H18 | 118.1 |
C5—C6—C7 | 123.85 (16) | C18—C19—C20 | 126.93 (16) |
C8—C7—C6 | 118.51 (15) | C18—C19—H19 | 116.5 |
C8—C7—C11 | 121.58 (15) | C20—C19—H19 | 116.5 |
C6—C7—C11 | 119.90 (14) | C21—C20—C19 | 127.31 (16) |
C7—C8—C9 | 119.67 (16) | C21—C20—S1 | 111.30 (13) |
C7—C8—C17 | 120.94 (15) | C19—C20—S1 | 121.39 (13) |
C9—C8—C17 | 119.35 (15) | C20—C21—C22 | 111.32 (18) |
N1—C9—C8 | 123.07 (15) | C20—C21—C24 | 125.56 (17) |
N1—C9—C10 | 116.42 (16) | C22—C21—C24 | 123.12 (18) |
C8—C9—C10 | 120.50 (17) | C23—C22—C21 | 113.90 (19) |
C9—C10—H10A | 109.5 | C23—C22—H22 | 123.1 |
C9—C10—H10B | 109.5 | C21—C22—H22 | 123.1 |
H10A—C10—H10B | 109.5 | C22—C23—S1 | 111.86 (15) |
C9—C10—H10C | 109.5 | C22—C23—H23 | 124.1 |
H10A—C10—H10C | 109.5 | S1—C23—H23 | 124.1 |
H10B—C10—H10C | 109.5 | C21—C24—H24A | 109.5 |
C12—C11—C16 | 118.55 (16) | C21—C24—H24B | 109.5 |
C12—C11—C7 | 120.36 (15) | H24A—C24—H24B | 109.5 |
C16—C11—C7 | 121.08 (16) | C21—C24—H24C | 109.5 |
C11—C12—C13 | 120.52 (17) | H24A—C24—H24C | 109.5 |
C11—C12—H12 | 119.7 | H24B—C24—H24C | 109.5 |
C9—N1—C1—C6 | −0.1 (3) | C8—C7—C11—C16 | −90.2 (2) |
C9—N1—C1—C2 | 178.26 (16) | C6—C7—C11—C16 | 91.0 (2) |
N1—C1—C2—C3 | −178.02 (18) | C16—C11—C12—C13 | −1.3 (3) |
C6—C1—C2—C3 | 0.4 (3) | C7—C11—C12—C13 | 178.36 (18) |
C1—C2—C3—C4 | −0.3 (3) | C11—C12—C13—C14 | 0.3 (3) |
C2—C3—C4—C5 | −0.1 (3) | C12—C13—C14—C15 | 0.8 (3) |
C3—C4—C5—C6 | 0.3 (3) | C13—C14—C15—C16 | −0.7 (3) |
N1—C1—C6—C5 | 178.14 (16) | C14—C15—C16—C11 | −0.3 (3) |
C2—C1—C6—C5 | −0.2 (2) | C12—C11—C16—C15 | 1.3 (3) |
N1—C1—C6—C7 | −1.3 (2) | C7—C11—C16—C15 | −178.31 (17) |
C2—C1—C6—C7 | −179.58 (15) | C7—C8—C17—O1 | −87.5 (2) |
C4—C5—C6—C1 | −0.1 (3) | C9—C8—C17—O1 | 90.2 (2) |
C4—C5—C6—C7 | 179.22 (17) | C7—C8—C17—C18 | 94.1 (2) |
C1—C6—C7—C8 | 1.2 (2) | C9—C8—C17—C18 | −88.2 (2) |
C5—C6—C7—C8 | −178.19 (16) | O1—C17—C18—C19 | −176.33 (18) |
C1—C6—C7—C11 | −179.93 (15) | C8—C17—C18—C19 | 2.0 (3) |
C5—C6—C7—C11 | 0.7 (2) | C17—C18—C19—C20 | 179.62 (16) |
C6—C7—C8—C9 | 0.1 (2) | C18—C19—C20—C21 | −172.65 (18) |
C11—C7—C8—C9 | −178.75 (15) | C18—C19—C20—S1 | 7.9 (3) |
C6—C7—C8—C17 | 177.80 (14) | C23—S1—C20—C21 | −0.25 (14) |
C11—C7—C8—C17 | −1.1 (2) | C23—S1—C20—C19 | 179.28 (15) |
C1—N1—C9—C8 | 1.5 (3) | C19—C20—C21—C22 | −179.31 (17) |
C1—N1—C9—C10 | −177.62 (17) | S1—C20—C21—C22 | 0.2 (2) |
C7—C8—C9—N1 | −1.6 (3) | C19—C20—C21—C24 | 1.0 (3) |
C17—C8—C9—N1 | −179.27 (15) | S1—C20—C21—C24 | −179.51 (16) |
C7—C8—C9—C10 | 177.54 (18) | C20—C21—C22—C23 | 0.0 (3) |
C17—C8—C9—C10 | −0.2 (3) | C24—C21—C22—C23 | 179.70 (19) |
C8—C7—C11—C12 | 90.2 (2) | C21—C22—C23—S1 | −0.2 (3) |
C6—C7—C11—C12 | −88.7 (2) | C20—S1—C23—C22 | 0.24 (17) |
Cg1 and Cg2 are the centroids of the S1,C20–C23 and N1,C1,C6–C9 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···Cg1i | 0.93 | 2.88 | 3.688 (2) | 146 |
C22—H22···Cg2ii | 0.93 | 2.60 | 3.457 (2) | 153 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C24H19NOS |
Mr | 369.46 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 10.0815 (7), 10.2956 (7), 10.5403 (7) |
α, β, γ (°) | 71.013 (6), 78.697 (5), 70.412 (6) |
V (Å3) | 969.99 (11) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.18 |
Crystal size (mm) | 0.40 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Agilent SuperNova Dual diffractometer with an Atlas detector |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2011) |
Tmin, Tmax | 0.780, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8430, 4473, 3484 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.651 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.135, 1.03 |
No. of reflections | 4473 |
No. of parameters | 246 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.26 |
Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).
Cg1 and Cg2 are the centroids of the S1,C20–C23 and N1,C1,C6–C9 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···Cg1i | 0.93 | 2.88 | 3.688 (2) | 146 |
C22—H22···Cg2ii | 0.93 | 2.60 | 3.457 (2) | 153 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z. |
Footnotes
‡Additional correspondence author, e-mail: juliebhavana@gmail.com.
Acknowledgements
PB and RP gratefully acknowledge the Council of Scientific and Industrial Research (CSIR), India, for research grant 02 (0076)/12/EMR-II and Senior Research Fellowship (09/919/(0014)/2012 EMR-I), respectively. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).
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.
In addition to their being valuable intermediates in organic synthesis (Prasath & Bhavana, 2012; Joshi et al., 2011), quinoline and heterocyclic analogues, such as chalcones, exhibit a variety of biological activities, e.g. anti-plasmodial, anti-microbial and anticancer activities (Prasath et al., 2013; Kalanithi et al., 2012). The title quinolinyl/chalcone bearing a thienyl substituent, (I), was investigated in the context of the above.
In (I), Fig. 1, the phenyl ring is perpendicular to the quinolinyl residue (r.m.s. deviation = 0.018 Å), forming a dihedral angle of 88.95 (8)°. The 3-thienyl ring also occupies a position approximately orthogonal to the quinolinyl residue with a dihedral angle of 81.98 (9)°. With respect to the plane through the quinolinyl residue, the carbonyl-O1 atom lies to one side, the carbonyl-C17 atom is almost co-planar and the remaining chalcone residue lies to the other side so that the molecule has an L-shape. The conformation about the ethylene bond [1.340 (2) Å] is E. A similar conformation and displacement of atoms was found in the most closely related structure, namely that of the recently reported (2E)-1-(2,4-dimethylquinolin-3-yl)-3-(thiophen-2-yl)prop-2-en-1-one (Prasath et al., 2011).
The most notable feature of the crystal packing is the formation of supramolecular chains along the b axis and sustained by C—H···π interactions between quinolinyl-C6—H4 and the 3-thienyl ring, and between 3-thienyl-H22 and the pyridyl ring, Fig. 2 and Table 1. Owing to the L-shape of the molecule, the chain has the shape of a square rod. Chains stack with no specific interactions between them, Fig. 3.