organic compounds
of diethyl 2-[(2-sulfanylquinolin-3-yl)methylidene]malonate
aDepartment of Physics, Govt. First Grade College, Davangere 577 004, Karnataka, India, bDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, cDepartment of Physics, Y. Y. D. Govt. First Grade College, Belur 573 115, Hassan, Karnataka, India, and dDepartment of Chemistry, Karnatak University's Karnatak Science College, Dharwad, Karnataka 580 001, India
*Correspondence e-mail: devarajegowda@yahoo.com
In the title compound, C17H17N O4S, the quinoline ring system is nearly planar, with a maximum deviation of 0.0496 (16) Å. A weak intramolecular C—H⋯O interaction is observed. In the crystal, C—H⋯O, S—H⋯N and π–π stacking interactions between the fused benzene ring of quinoline and the pyridine moieties [shortest centroid–centroid distance = 3.6754 (11) Å] are observed. Inversion-related weak C—H⋯O intermolecular interactions diagonally along [010], with R22(10) ring motifs, and S—H⋯N intermolecular interactions diagonally along [100], with R22(8) ring motifs, are present, forming a three-dimensional network structure. No classical hydrogen bonds are observed.
Keywords: crystal structure; diester; quinoline; malonate; intermolecular interactions.
CCDC reference: 1413116
1. Related literature
For biological applications of quinolines, see: Nandeshwarappa et al.(2006); Noda et al. (2001); Pandey et al. (2004); Sharma et al. (2008).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014.
Supporting information
CCDC reference: 1413116
https://doi.org/10.1107/S2056989015013596/jj2194sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015013596/jj2194Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015013596/jj2194Isup3.cml
All the chemicals of analytical reagent grade were used directly without further purification. An equimolar quantity of 2-mercapto-3-formyl quinoline (0.01 mm) and diethylmalonate (0.001mm) were refluxed for 24 hr in acetonitrile at 353 K. After completion of the reaction the solvent was removed from the vacuue and recrystalized from ethanol. Yellow needles of the title compound were grown from ethanol solution by slow evaporation at room temperature. Colour: Yellow. Yield= 82%, m.p.:458 K.
All H atoms were positioned geometrically, with S—H = 1.2 Å, C—H = 0.93 Å for aromatic H, C—H = 0.97 Å for methylene H and C—H = 0.96 Å for methyl H,and refined using a riding model with Uiso(H) = 1.5Ueq(C) for methyl H and Uiso(H) = 1.2Ueq(C) for all other H.
Quinolines are a heterocyclic class of organic compounds containing a pyridine ring fused with benzene found in nature mainly in plants. Alkaloid quinine is a traditional anti-malarial drug also used in tonics. The quinoline skeleton has since been used as a basis for design of many synthetic anti-malarial compounds, of which chloroquinoline is one such example. Despite its relatively low efficacy and tolerability, quinine still plays an important role in the treatment of multi resistant malaria (Nandeshwarappa et al.2006). It has also played a historical role in organic chemistry as a target for structural determination and total synthesis reactions (Sharma et al.2008), as well as stereo selective (Noda et al.2001) and enantio selective (Pande et al., 2004) total synthesis reactions. The chemistry of quinoline has gained increasing attention due to its various diverse pharmacological activities. We report herin the
of a new quinoline derivative, diethyl 2-((2-mercaptoquinolin-3-yl) methylene)malonate, C17H17N O4S, (I) (Fig. 1).In the π–π stacking interactions between the fused benzene ring of quinoline, Cg(2) [C10—C15], and pyridine, Cg(1) [N6//C7–C11], [shortest centroid–centroid distance = 3.6751 (11) Å] are observed. Inversion related weak C—H···O intermolecular interactions diagonally along [010] with R22(10) ring motifs and S—H···N intermolecular interactions diagonally along [100] with R22(8) ring motifs are present forming a three-dimensional network structure (Fig. 2). No classical hydrogen bonds are observed.
of (I), the quinoline ring system is nearly planar, with a maximum deviation of 0.0496 (16) Å for atom C8. In the crystal, weak intramolecular C—H···O, intermolecular C—H···O, S—H···N (Table 1) andFor biological applications of quinolines, see: Nandeshwarappa et al.(2006); Noda et al. (2001); Pandey et al. (2004); Sharma et al. (2008).
Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).Fig. 1. ORTEP diagram of the title compound, C17H17N O4S. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius. | |
Fig. 2. A view of the packing in the title molecule, C17H17N O4S, along the a axis. Dashed lines indicate weak C—H···O and S—H···N intermolecular interactions with inversio- related C—H···O intermolecular interactions diagonally along [010] with R22(10) ring motifs and S—H···N intermolecular interactions diagonally along [100] with R22(8) ring motifs forming a three-dimensional network structure. |
C17H17NO4S | F(000) = 348 |
Mr = 331.37 | Dx = 1.337 Mg m−3 |
Triclinic, P1 | Melting point: 458 K |
a = 7.3739 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.8148 (4) Å | Cell parameters from 5853 reflections |
c = 15.8149 (7) Å | θ = 2.6–32.5° |
α = 90.158 (2)° | µ = 0.22 mm−1 |
β = 99.486 (2)° | T = 296 K |
γ = 113.301 (2)° | Plate, yellow |
V = 823.24 (7) Å3 | 0.24 × 0.20 × 0.12 mm |
Z = 2 |
Bruker SMART CCD area-detector diffractometer | 5853 independent reflections |
Radiation source: fine-focus sealed tube | 4295 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 10.0 pixels mm-1 | θmax = 32.5°, θmin = 2.6° |
ω and φ scans | h = −11→10 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) | k = −11→11 |
Tmin = 0.770, Tmax = 1.000 | l = −23→23 |
21213 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.062 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.213 | w = 1/[σ2(Fo2) + (0.1265P)2 + 0.1563P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
5853 reflections | Δρmax = 0.98 e Å−3 |
234 parameters | Δρmin = −0.48 e Å−3 |
C17H17NO4S | γ = 113.301 (2)° |
Mr = 331.37 | V = 823.24 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.3739 (4) Å | Mo Kα radiation |
b = 7.8148 (4) Å | µ = 0.22 mm−1 |
c = 15.8149 (7) Å | T = 296 K |
α = 90.158 (2)° | 0.24 × 0.20 × 0.12 mm |
β = 99.486 (2)° |
Bruker SMART CCD area-detector diffractometer | 5853 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) | 4295 reflections with I > 2σ(I) |
Tmin = 0.770, Tmax = 1.000 | Rint = 0.025 |
21213 measured reflections |
R[F2 > 2σ(F2)] = 0.062 | 0 restraints |
wR(F2) = 0.213 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.98 e Å−3 |
5853 reflections | Δρmin = −0.48 e Å−3 |
234 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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.89170 (8) | 0.93555 (6) | 0.36268 (3) | 0.05361 (17) | |
H1 | 0.9130 | 1.0542 | 0.4163 | 0.080* | |
O2 | 0.9018 (3) | 0.6179 (2) | 0.10198 (11) | 0.0741 (5) | |
O3 | 0.6426 (2) | 0.3469 (2) | 0.05791 (8) | 0.0546 (3) | |
O4 | 0.5360 (3) | 0.1266 (2) | 0.23539 (12) | 0.0772 (5) | |
O5 | 0.3614 (2) | 0.2881 (2) | 0.17989 (10) | 0.0584 (4) | |
N6 | 0.8126 (2) | 0.71751 (18) | 0.48999 (9) | 0.0417 (3) | |
C7 | 0.8326 (2) | 0.7292 (2) | 0.40651 (10) | 0.0380 (3) | |
C8 | 0.7963 (2) | 0.5561 (2) | 0.35911 (10) | 0.0370 (3) | |
C9 | 0.7551 (2) | 0.3953 (2) | 0.40069 (10) | 0.0398 (3) | |
C10 | 0.7342 (2) | 0.3901 (2) | 0.48846 (10) | 0.0383 (3) | |
C11 | 0.7609 (2) | 0.5567 (2) | 0.53269 (10) | 0.0388 (3) | |
C12 | 0.7363 (3) | 0.5596 (3) | 0.61848 (11) | 0.0491 (4) | |
C13 | 0.6855 (3) | 0.3962 (3) | 0.65909 (13) | 0.0552 (4) | |
C14 | 0.6621 (3) | 0.2299 (3) | 0.61664 (14) | 0.0555 (5) | |
C15 | 0.6872 (3) | 0.2268 (2) | 0.53337 (13) | 0.0480 (4) | |
C16 | 0.8203 (2) | 0.5658 (2) | 0.26908 (10) | 0.0409 (3) | |
C17 | 0.7083 (2) | 0.4422 (2) | 0.20334 (10) | 0.0408 (3) | |
C18 | 0.5287 (3) | 0.2679 (2) | 0.20902 (10) | 0.0452 (4) | |
C19 | 0.7642 (3) | 0.4825 (3) | 0.11661 (11) | 0.0480 (4) | |
C20 | 0.1759 (3) | 0.1201 (4) | 0.17362 (19) | 0.0786 (7) | |
H20A | 0.1767 | 0.0250 | 0.1343 | 0.094* | |
H20B | 0.1638 | 0.0706 | 0.2296 | 0.094* | |
C21 | 0.0112 (5) | 0.1699 (7) | 0.1429 (4) | 0.153 (2) | |
H21A | 0.0306 | 0.2843 | 0.1731 | 0.229* | |
H21B | −0.1114 | 0.0724 | 0.1525 | 0.229* | |
H21C | 0.0038 | 0.1864 | 0.0825 | 0.229* | |
C22 | 0.6792 (4) | 0.3723 (4) | −0.03002 (13) | 0.0671 (6) | |
H22A | 0.6744 | 0.4891 | −0.0482 | 0.081* | |
H22B | 0.8109 | 0.3761 | −0.0333 | 0.081* | |
C23 | 0.5247 (5) | 0.2163 (5) | −0.08543 (16) | 0.0886 (9) | |
H23A | 0.5372 | 0.1023 | −0.0698 | 0.133* | |
H23B | 0.5403 | 0.2350 | −0.1442 | 0.133* | |
H23C | 0.3946 | 0.2086 | −0.0788 | 0.133* | |
H9 | 0.737 (4) | 0.276 (4) | 0.3721 (18) | 0.066 (7)* | |
H12 | 0.762 (4) | 0.689 (4) | 0.6437 (17) | 0.063 (7)* | |
H13 | 0.658 (4) | 0.395 (4) | 0.715 (2) | 0.079 (8)* | |
H14 | 0.628 (5) | 0.139 (5) | 0.643 (2) | 0.081 (9)* | |
H15 | 0.659 (4) | 0.107 (4) | 0.5002 (17) | 0.067 (7)* | |
H16 | 0.917 (3) | 0.662 (3) | 0.2553 (14) | 0.044 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0738 (3) | 0.0359 (2) | 0.0479 (3) | 0.0171 (2) | 0.0148 (2) | 0.00743 (17) |
O2 | 0.0679 (9) | 0.0726 (10) | 0.0589 (8) | −0.0024 (8) | 0.0283 (7) | −0.0006 (7) |
O3 | 0.0549 (7) | 0.0603 (8) | 0.0379 (6) | 0.0098 (6) | 0.0140 (5) | −0.0042 (5) |
O4 | 0.0872 (12) | 0.0437 (7) | 0.0777 (11) | 0.0108 (7) | −0.0076 (9) | 0.0067 (7) |
O5 | 0.0415 (6) | 0.0578 (8) | 0.0658 (8) | 0.0070 (5) | 0.0153 (6) | 0.0071 (6) |
N6 | 0.0510 (7) | 0.0334 (6) | 0.0386 (6) | 0.0135 (5) | 0.0112 (5) | 0.0010 (5) |
C7 | 0.0385 (7) | 0.0340 (6) | 0.0382 (7) | 0.0113 (5) | 0.0064 (5) | 0.0000 (5) |
C8 | 0.0334 (6) | 0.0358 (6) | 0.0370 (6) | 0.0097 (5) | 0.0042 (5) | −0.0023 (5) |
C9 | 0.0377 (7) | 0.0339 (6) | 0.0426 (7) | 0.0109 (5) | 0.0021 (5) | −0.0043 (5) |
C10 | 0.0329 (6) | 0.0341 (6) | 0.0424 (7) | 0.0089 (5) | 0.0037 (5) | 0.0026 (5) |
C11 | 0.0365 (7) | 0.0365 (7) | 0.0400 (7) | 0.0107 (5) | 0.0080 (5) | 0.0040 (5) |
C12 | 0.0539 (9) | 0.0499 (9) | 0.0425 (8) | 0.0176 (7) | 0.0146 (7) | 0.0047 (7) |
C13 | 0.0530 (10) | 0.0634 (11) | 0.0481 (9) | 0.0188 (8) | 0.0174 (8) | 0.0153 (8) |
C14 | 0.0499 (9) | 0.0497 (10) | 0.0597 (11) | 0.0121 (7) | 0.0108 (8) | 0.0200 (8) |
C15 | 0.0440 (8) | 0.0370 (7) | 0.0558 (9) | 0.0104 (6) | 0.0049 (7) | 0.0077 (7) |
C16 | 0.0379 (7) | 0.0400 (7) | 0.0408 (7) | 0.0112 (6) | 0.0082 (6) | −0.0002 (6) |
C17 | 0.0396 (7) | 0.0429 (7) | 0.0370 (7) | 0.0128 (6) | 0.0090 (5) | 0.0005 (6) |
C18 | 0.0496 (8) | 0.0419 (8) | 0.0340 (7) | 0.0084 (6) | 0.0062 (6) | −0.0028 (6) |
C19 | 0.0449 (8) | 0.0536 (9) | 0.0419 (8) | 0.0142 (7) | 0.0128 (6) | 0.0002 (7) |
C20 | 0.0509 (11) | 0.0720 (15) | 0.0844 (16) | −0.0077 (10) | 0.0189 (11) | 0.0015 (12) |
C21 | 0.0525 (17) | 0.125 (3) | 0.240 (6) | 0.0057 (18) | −0.007 (2) | 0.052 (4) |
C22 | 0.0709 (13) | 0.0810 (15) | 0.0411 (9) | 0.0172 (11) | 0.0226 (9) | 0.0020 (9) |
C23 | 0.115 (2) | 0.0886 (19) | 0.0448 (11) | 0.0240 (17) | 0.0127 (12) | −0.0065 (11) |
S1—C7 | 1.6796 (16) | C13—H13 | 0.94 (3) |
S1—H1 | 1.2000 | C14—C15 | 1.361 (3) |
O2—C19 | 1.197 (2) | C14—H14 | 0.80 (3) |
O3—C19 | 1.326 (2) | C15—H15 | 1.00 (3) |
O3—C22 | 1.459 (2) | C16—C17 | 1.333 (2) |
O4—C18 | 1.199 (2) | C16—H16 | 0.86 (2) |
O5—C18 | 1.314 (2) | C17—C18 | 1.494 (2) |
O5—C20 | 1.462 (3) | C17—C19 | 1.495 (2) |
N6—C7 | 1.352 (2) | C20—C21 | 1.429 (5) |
N6—C11 | 1.375 (2) | C20—H20A | 0.9700 |
C7—C8 | 1.451 (2) | C20—H20B | 0.9700 |
C8—C9 | 1.369 (2) | C21—H21A | 0.9600 |
C8—C16 | 1.462 (2) | C21—H21B | 0.9600 |
C9—C10 | 1.421 (2) | C21—H21C | 0.9600 |
C9—H9 | 0.99 (3) | C22—C23 | 1.456 (4) |
C10—C11 | 1.403 (2) | C22—H22A | 0.9700 |
C10—C15 | 1.411 (2) | C22—H22B | 0.9700 |
C11—C12 | 1.399 (2) | C23—H23A | 0.9600 |
C12—C13 | 1.374 (3) | C23—H23B | 0.9600 |
C12—H12 | 1.02 (3) | C23—H23C | 0.9600 |
C13—C14 | 1.396 (3) | ||
C7—S1—H1 | 109.5 | C16—C17—C18 | 125.18 (14) |
C19—O3—C22 | 116.21 (16) | C16—C17—C19 | 117.59 (15) |
C18—O5—C20 | 116.10 (19) | C18—C17—C19 | 117.22 (14) |
C7—N6—C11 | 125.49 (13) | O4—C18—O5 | 124.31 (18) |
N6—C7—C8 | 116.36 (14) | O4—C18—C17 | 124.41 (18) |
N6—C7—S1 | 119.98 (11) | O5—C18—C17 | 111.27 (15) |
C8—C7—S1 | 123.65 (12) | O2—C19—O3 | 124.24 (16) |
C9—C8—C7 | 119.72 (14) | O2—C19—C17 | 124.71 (17) |
C9—C8—C16 | 122.79 (14) | O3—C19—C17 | 111.04 (15) |
C7—C8—C16 | 117.33 (14) | C21—C20—O5 | 108.0 (3) |
C8—C9—C10 | 121.62 (14) | C21—C20—H20A | 110.1 |
C8—C9—H9 | 122.7 (16) | O5—C20—H20A | 110.1 |
C10—C9—H9 | 115.7 (16) | C21—C20—H20B | 110.1 |
C11—C10—C15 | 118.31 (15) | O5—C20—H20B | 110.1 |
C11—C10—C9 | 118.09 (14) | H20A—C20—H20B | 108.4 |
C15—C10—C9 | 123.61 (15) | C20—C21—H21A | 109.5 |
N6—C11—C12 | 120.63 (14) | C20—C21—H21B | 109.5 |
N6—C11—C10 | 118.56 (14) | H21A—C21—H21B | 109.5 |
C12—C11—C10 | 120.81 (15) | C20—C21—H21C | 109.5 |
C13—C12—C11 | 118.92 (17) | H21A—C21—H21C | 109.5 |
C13—C12—H12 | 127.7 (14) | H21B—C21—H21C | 109.5 |
C11—C12—H12 | 113.3 (14) | C23—C22—O3 | 108.17 (19) |
C12—C13—C14 | 121.07 (18) | C23—C22—H22A | 110.1 |
C12—C13—H13 | 119.0 (18) | O3—C22—H22A | 110.1 |
C14—C13—H13 | 119.8 (18) | C23—C22—H22B | 110.1 |
C15—C14—C13 | 120.20 (17) | O3—C22—H22B | 110.1 |
C15—C14—H14 | 124 (2) | H22A—C22—H22B | 108.4 |
C13—C14—H14 | 116 (2) | C22—C23—H23A | 109.5 |
C14—C15—C10 | 120.66 (17) | C22—C23—H23B | 109.5 |
C14—C15—H15 | 121.4 (15) | H23A—C23—H23B | 109.5 |
C10—C15—H15 | 117.6 (15) | C22—C23—H23C | 109.5 |
C17—C16—C8 | 127.50 (15) | H23A—C23—H23C | 109.5 |
C17—C16—H16 | 114.3 (14) | H23B—C23—H23C | 109.5 |
C8—C16—H16 | 118.2 (14) | ||
C11—N6—C7—C8 | −0.1 (2) | C11—C10—C15—C14 | 2.2 (2) |
C11—N6—C7—S1 | 178.63 (13) | C9—C10—C15—C14 | −177.58 (16) |
N6—C7—C8—C9 | −3.4 (2) | C9—C8—C16—C17 | 42.8 (3) |
S1—C7—C8—C9 | 177.93 (12) | C7—C8—C16—C17 | −141.69 (17) |
N6—C7—C8—C16 | −179.02 (14) | C8—C16—C17—C18 | 1.8 (3) |
S1—C7—C8—C16 | 2.3 (2) | C8—C16—C17—C19 | −179.45 (16) |
C7—C8—C9—C10 | 4.1 (2) | C20—O5—C18—O4 | −5.2 (3) |
C16—C8—C9—C10 | 179.47 (14) | C20—O5—C18—C17 | 173.63 (17) |
C8—C9—C10—C11 | −1.3 (2) | C16—C17—C18—O4 | −78.9 (3) |
C8—C9—C10—C15 | 178.46 (15) | C19—C17—C18—O4 | 102.4 (2) |
C7—N6—C11—C12 | −177.33 (16) | C16—C17—C18—O5 | 102.3 (2) |
C7—N6—C11—C10 | 2.9 (2) | C19—C17—C18—O5 | −76.47 (19) |
C15—C10—C11—N6 | 178.10 (14) | C22—O3—C19—O2 | −2.2 (3) |
C9—C10—C11—N6 | −2.1 (2) | C22—O3—C19—C17 | 178.64 (18) |
C15—C10—C11—C12 | −1.7 (2) | C16—C17—C19—O2 | −0.2 (3) |
C9—C10—C11—C12 | 178.05 (15) | C18—C17—C19—O2 | 178.7 (2) |
N6—C11—C12—C13 | −179.72 (17) | C16—C17—C19—O3 | 178.96 (16) |
C10—C11—C12—C13 | 0.1 (3) | C18—C17—C19—O3 | −2.2 (2) |
C11—C12—C13—C14 | 1.2 (3) | C18—O5—C20—C21 | 178.7 (3) |
C12—C13—C14—C15 | −0.7 (3) | C19—O3—C22—C23 | −176.6 (2) |
C13—C14—C15—C10 | −1.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
S1—H1···N6i | 1.20 | 2.37 | 3.3389 (14) | 136 |
C9—H9···O4 | 0.99 (3) | 2.41 (3) | 3.122 (2) | 129 (2) |
C22—H22B···O2ii | 0.97 | 2.52 | 3.438 (4) | 158 |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+2, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
S1—H1···N6i | 1.20 | 2.3700 | 3.3389 (14) | 136.00 |
C9—H9···O4 | 0.99 (3) | 2.41 (3) | 3.122 (2) | 129 (2) |
C22—H22B···O2ii | 0.97 | 2.5200 | 3.438 (4) | 158 |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+2, −y+1, −z. |
Acknowledgements
The authors thank to Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad for CCD X-ray facilities, the X-ray data collection, GCMS, IR, CHNS and NMR data, and the UGC, New Delhi, for financial assistance.
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Quinolines are a heterocyclic class of organic compounds containing a pyridine ring fused with benzene found in nature mainly in plants. Alkaloid quinine is a traditional anti-malarial drug also used in tonics. The quinoline skeleton has since been used as a basis for design of many synthetic anti-malarial compounds, of which chloroquinoline is one such example. Despite its relatively low efficacy and tolerability, quinine still plays an important role in the treatment of multi resistant malaria (Nandeshwarappa et al.2006). It has also played a historical role in organic chemistry as a target for structural determination and total synthesis reactions (Sharma et al.2008), as well as stereo selective (Noda et al.2001) and enantio selective (Pande et al., 2004) total synthesis reactions. The chemistry of quinoline has gained increasing attention due to its various diverse pharmacological activities. We report herin the crystal structure of a new quinoline derivative, diethyl 2-((2-mercaptoquinolin-3-yl) methylene)malonate, C17H17N O4S, (I) (Fig. 1).
In the asymmetric unit of (I), the quinoline ring system is nearly planar, with a maximum deviation of 0.0496 (16) Å for atom C8. In the crystal, weak intramolecular C—H···O, intermolecular C—H···O, S—H···N (Table 1) and π–π stacking interactions between the fused benzene ring of quinoline, Cg(2) [C10—C15], and pyridine, Cg(1) [N6//C7–C11], [shortest centroid–centroid distance = 3.6751 (11) Å] are observed. Inversion related weak C—H···O intermolecular interactions diagonally along [010] with R22(10) ring motifs and S—H···N intermolecular interactions diagonally along [100] with R22(8) ring motifs are present forming a three-dimensional network structure (Fig. 2). No classical hydrogen bonds are observed.