organic compounds
2-(4-Methylphenyl)quinoline-4-carboxylic acid
aDepartment of Chemistry, The University of Jordan, Amman 11942, Jordan
*Correspondence e-mail: r.alqawasmeh@ju.edu.jo
In the title compound, C17H13NO2, the dihedral angle between the plane of the carboxy group and the quinoline mean plane is 45.05 (13)°, and that between the toluene ring mean plane and the quinoline mean plane is 25.29 (7)°. In the crystal, molecules are linked via O—H⋯.N hydrogen bonds, forming chains propagating along the b-axis direction. These chain are linked via C—H⋯O interactions, forming two-dimensional networks lying parallel to the ab plane.
Related literature
For the importance of the quinoline carboxylic acid analogues in the synthesis of various compounds with pharmacological properties, see: Deady et al. (1999, 2011); Kalluraya & Sreenivasa (1998); Tseng et al. (2008); Kravchenko et al. (2005). The structure of the related compound 2-phenylquinoline-4-carboxlic acid is described by Blackburn et al. (1996). For a description of puckering analysis, see: Cremer & Pople (1975). For synthetic preparation, see: Pfitzinger (1886).
Experimental
Crystal data
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Data collection
Refinement
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Data collection: CrysAlis PRO (Oxford Diffraction, 2009); 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: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2.
Supporting information
https://doi.org/10.1107/S160053681203797X/go2066sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681203797X/go2066Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S160053681203797X/go2066Isup3.cml
The title compound was synthesized according to Pfitzinger reaction (Pfitzinger, 1886). Herein, we use the microwave technology for this synthesis, in a typical procedure: a mixture of isatin (1 mmole), acetophenone (1.05 equivalents) and potassium hydroxide (10 equivalents) in aqueous ethanol (10 ml) was placed in a closed vessel and irradiated with MW for 12 minutes at 140°C. The reaction mixture was acidified with acetic acid and the product was recrystallized from ethanol to produce white crystals with a melting point of 214–216 °C. Crystal with two different morphologies were found, cubic crystals which did not produce good diffraction and needle-shaped crystals. A large needle crystal was selected since the others were too small to provide good diffraction data.
All H atoms attached to C atoms were treated as riding atoms with C—H(aromatic), 0.93Å and C—H(methyl), 0.96Å, with Uiso = 1.2Ueq().
The H atom attached to the carboxylic -OH was located on a difference map and refined isotropically.
The positions of the methyl and hydroxyl hydrogen were checked on a final difference map.
Quinoline derivatives are widely used as synthons for biologically important compounds (Tseng et al., 2008), (Kravchenko et al., 2005). In our group this moiety was used to synthesize new antitumor as well as antibacterial agents. The title molecule is shown in Fig. 1 with the numbering scheme. The dihedral angle between the plane of the carboxyl group and the quinoline mean plane is 45.05 (13)° and that between the toluene ring mean plane and the quinoline mean plane is 25.29 (7)°. The total puckering amplitude, Q, (Cremer & Pople, 1975) for the quinoline ring in the title compound is 0.044 (2)Å in the title compound as compared with the value of 0.080 (3) Å in the closely related compound 2-phenylquinoline-4-carboxlic acid (Blackburn et al., 1996). There is a hydrogen bond between the carboxylic acid oxygen atom, O1 and N1 in the quinoline ring, Table 1, Figure 2. In addition the molecules are linked by a weak C-H..O interaction between C3 and O1, Table 1. There is π–π stacking between molecules Molecules are stacked above and below one another with unit translation along the a-axis so that rings containing N1 stack above those containing N1, the same applies to the rings containing C1 and C12. This results in π–π stacking between the molecules: i) between rings containing N1 (centroid Cg1) [Cg1···Cg1(-1+x, y, z), centroid to centroid distance: 4.1001 (13) Å, perpendicular distance between rings: 3.7681 (8) Å slippage: 1.616Å] and ii) between rings containing C1, (centroid Cg2), [Cg2···Cg2(-1+x ,y, z), centroid to centroid distance 4.1000 (14) Å, perpendicular distance between rings 3.3521 (8) Å, slippage 2.361Å] and iii) between rings containing C12 (centroid Cg3) Cg3···Cg3 (-1+x, y, z), [centroid to centroid) distance 4.1003 (17) Å, perpendicular distance between rings 3.7411 (11)Å, slippage 1.678Å].
For the importance of the quinoline carboxylic acid analogues in the synthesis of various compounds with pharmacological properties, see: Deady et al. (1999, 2011); Kalluraya & Sreenivasa (1998); Tseng et al. (2008); Kravchenko et al. (2005). The structure of the related compound 2-phenylquinoline-4-carboxlic acid is described by Blackburn et al. (1996). For a description of puckering analysis, see: Cremer & Pople (1975). For synthetic preparation, see: Pfitzinger (1886).
Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell
CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).C17H13NO2 | F(000) = 552 |
Mr = 263.28 | Dx = 1.369 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1144 reflections |
a = 4.1001 (6) Å | θ = 3.0–29.0° |
b = 15.3464 (11) Å | µ = 0.09 mm−1 |
c = 20.3037 (17) Å | T = 291 K |
β = 90.859 (9)° | Needle, clear colourless |
V = 1277.4 (2) Å3 | 0.70 × 0.08 × 0.05 mm |
Z = 4 |
Oxford Diffraction Xcalibur Eos diffractometer | 2238 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1747 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 16.0534 pixels mm-1 | θmax = 25.0°, θmin = 3.3° |
ω scans | h = −4→4 |
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009), based on expressions derived from Clark & Reid (1995)] | k = −18→12 |
Tmin = 0.992, Tmax = 0.999 | l = −24→15 |
4867 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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0574P)2 + 0.213P] where P = (Fo2 + 2Fc2)/3 |
2238 reflections | (Δ/σ)max = 0.001 |
186 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C17H13NO2 | V = 1277.4 (2) Å3 |
Mr = 263.28 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 4.1001 (6) Å | µ = 0.09 mm−1 |
b = 15.3464 (11) Å | T = 291 K |
c = 20.3037 (17) Å | 0.70 × 0.08 × 0.05 mm |
β = 90.859 (9)° |
Oxford Diffraction Xcalibur Eos diffractometer | 2238 independent reflections |
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009), based on expressions derived from Clark & Reid (1995)] | 1747 reflections with I > 2σ(I) |
Tmin = 0.992, Tmax = 0.999 | Rint = 0.025 |
4867 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.126 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.20 e Å−3 |
2238 reflections | Δρmin = −0.24 e Å−3 |
186 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 | ||
O1 | 0.5305 (4) | 0.25205 (9) | 0.25810 (7) | 0.0455 (4) | |
O2 | 0.7609 (5) | 0.28629 (9) | 0.16337 (8) | 0.0636 (6) | |
N1 | 0.3552 (4) | 0.57466 (9) | 0.24364 (7) | 0.0347 (4) | |
C1 | −0.0757 (5) | 0.69209 (12) | 0.02784 (10) | 0.0371 (5) | |
C2 | −0.1462 (5) | 0.71004 (12) | 0.09272 (10) | 0.0385 (5) | |
H2 | −0.2786 | 0.7574 | 0.1024 | 0.046* | |
C3 | −0.0247 (5) | 0.65926 (12) | 0.14342 (9) | 0.0350 (5) | |
H3 | −0.0740 | 0.6734 | 0.1867 | 0.042* | |
C4 | 0.1703 (5) | 0.58721 (11) | 0.13094 (9) | 0.0316 (5) | |
C5 | 0.2352 (6) | 0.56779 (12) | 0.06552 (9) | 0.0382 (5) | |
H5 | 0.3618 | 0.5194 | 0.0556 | 0.046* | |
C6 | 0.1145 (5) | 0.61934 (13) | 0.01517 (10) | 0.0398 (5) | |
H6 | 0.1615 | 0.6051 | −0.0282 | 0.048* | |
C7 | 0.3111 (5) | 0.53556 (11) | 0.18595 (9) | 0.0315 (5) | |
C8 | 0.3996 (5) | 0.44729 (11) | 0.17666 (9) | 0.0346 (5) | |
H8 | 0.3658 | 0.4214 | 0.1357 | 0.041* | |
C9 | 0.5335 (5) | 0.39967 (11) | 0.22678 (9) | 0.0331 (5) | |
C10 | 0.5825 (5) | 0.43954 (11) | 0.28941 (9) | 0.0346 (5) | |
C11 | 0.4852 (6) | 0.52799 (12) | 0.29539 (9) | 0.0365 (5) | |
C12 | 0.5238 (7) | 0.57039 (13) | 0.35660 (10) | 0.0529 (7) | |
H12 | 0.4589 | 0.6281 | 0.3612 | 0.064* | |
C13 | 0.6553 (8) | 0.52727 (14) | 0.40883 (11) | 0.0630 (8) | |
H13 | 0.6767 | 0.5555 | 0.4492 | 0.076* | |
C14 | 0.7593 (7) | 0.44087 (14) | 0.40289 (11) | 0.0585 (7) | |
H14 | 0.8527 | 0.4126 | 0.4390 | 0.070* | |
C15 | 0.7249 (6) | 0.39806 (13) | 0.34481 (10) | 0.0456 (6) | |
H15 | 0.7960 | 0.3407 | 0.3414 | 0.055* | |
C16 | 0.6231 (5) | 0.30697 (12) | 0.21252 (10) | 0.0360 (5) | |
C17 | −0.2037 (7) | 0.74933 (14) | −0.02685 (11) | 0.0532 (6) | |
H17A | −0.2977 | 0.7137 | −0.0610 | 0.064* | |
H17B | −0.0278 | 0.7830 | −0.0444 | 0.064* | |
H17C | −0.3670 | 0.7878 | −0.0100 | 0.064* | |
H1 | 0.582 (7) | 0.1965 (19) | 0.2521 (12) | 0.072 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0703 (12) | 0.0208 (7) | 0.0457 (9) | 0.0014 (7) | 0.0106 (8) | 0.0032 (6) |
O2 | 0.1040 (16) | 0.0342 (8) | 0.0534 (10) | 0.0071 (9) | 0.0301 (10) | −0.0010 (7) |
N1 | 0.0480 (11) | 0.0239 (8) | 0.0324 (9) | −0.0006 (7) | 0.0012 (8) | 0.0016 (7) |
C1 | 0.0379 (13) | 0.0319 (11) | 0.0414 (12) | −0.0059 (9) | −0.0056 (9) | 0.0034 (9) |
C2 | 0.0379 (13) | 0.0281 (10) | 0.0493 (13) | 0.0039 (9) | −0.0034 (10) | 0.0002 (9) |
C3 | 0.0385 (13) | 0.0307 (10) | 0.0360 (11) | −0.0017 (9) | 0.0016 (9) | −0.0031 (8) |
C4 | 0.0364 (12) | 0.0229 (9) | 0.0356 (11) | −0.0058 (8) | 0.0009 (9) | −0.0002 (8) |
C5 | 0.0476 (14) | 0.0283 (10) | 0.0388 (12) | 0.0018 (9) | 0.0017 (10) | −0.0030 (8) |
C6 | 0.0489 (14) | 0.0389 (11) | 0.0315 (11) | −0.0006 (10) | 0.0002 (9) | 0.0002 (9) |
C7 | 0.0371 (12) | 0.0237 (9) | 0.0338 (11) | −0.0038 (8) | 0.0043 (9) | 0.0013 (8) |
C8 | 0.0467 (13) | 0.0237 (10) | 0.0332 (11) | −0.0016 (9) | 0.0003 (9) | −0.0018 (8) |
C9 | 0.0396 (13) | 0.0227 (9) | 0.0369 (11) | −0.0029 (8) | 0.0030 (9) | 0.0010 (8) |
C10 | 0.0440 (13) | 0.0225 (9) | 0.0371 (11) | −0.0047 (9) | 0.0003 (9) | 0.0021 (8) |
C11 | 0.0520 (14) | 0.0238 (10) | 0.0338 (11) | −0.0029 (9) | −0.0004 (9) | 0.0029 (8) |
C12 | 0.090 (2) | 0.0286 (11) | 0.0396 (13) | 0.0023 (12) | −0.0062 (12) | −0.0028 (9) |
C13 | 0.110 (2) | 0.0386 (13) | 0.0395 (13) | −0.0017 (14) | −0.0164 (13) | −0.0051 (10) |
C14 | 0.092 (2) | 0.0380 (12) | 0.0446 (14) | 0.0000 (13) | −0.0220 (13) | 0.0045 (10) |
C15 | 0.0641 (16) | 0.0280 (10) | 0.0444 (13) | 0.0025 (10) | −0.0095 (11) | 0.0026 (9) |
C16 | 0.0462 (14) | 0.0246 (10) | 0.0373 (11) | −0.0013 (9) | 0.0015 (10) | 0.0011 (8) |
C17 | 0.0620 (17) | 0.0482 (13) | 0.0490 (13) | 0.0059 (12) | −0.0083 (12) | 0.0107 (10) |
O1—C16 | 1.312 (2) | C8—C9 | 1.362 (3) |
O1—H1 | 0.89 (3) | C8—H8 | 0.9300 |
O2—C16 | 1.197 (2) | C9—C10 | 1.423 (3) |
N1—C7 | 1.326 (2) | C9—C16 | 1.499 (3) |
N1—C11 | 1.372 (2) | C10—C15 | 1.411 (3) |
C1—C2 | 1.381 (3) | C10—C11 | 1.421 (3) |
C1—C6 | 1.388 (3) | C11—C12 | 1.410 (3) |
C1—C17 | 1.504 (3) | C12—C13 | 1.355 (3) |
C2—C3 | 1.378 (3) | C12—H12 | 0.9300 |
C2—H2 | 0.9300 | C13—C14 | 1.399 (3) |
C3—C4 | 1.390 (3) | C13—H13 | 0.9300 |
C3—H3 | 0.9300 | C14—C15 | 1.355 (3) |
C4—C5 | 1.391 (3) | C14—H14 | 0.9300 |
C4—C7 | 1.480 (3) | C15—H15 | 0.9300 |
C5—C6 | 1.379 (3) | C17—H17A | 0.9600 |
C5—H5 | 0.9300 | C17—H17B | 0.9600 |
C6—H6 | 0.9300 | C17—H17C | 0.9600 |
C7—C8 | 1.416 (3) | ||
C16—O1—H1 | 116.7 (16) | C10—C9—C16 | 123.30 (18) |
C7—N1—C11 | 119.10 (15) | C15—C10—C11 | 118.45 (17) |
C2—C1—C6 | 117.62 (18) | C15—C10—C9 | 124.72 (17) |
C2—C1—C17 | 120.81 (19) | C11—C10—C9 | 116.82 (17) |
C6—C1—C17 | 121.57 (19) | N1—C11—C12 | 118.12 (17) |
C3—C2—C1 | 121.42 (18) | N1—C11—C10 | 122.65 (17) |
C3—C2—H2 | 119.3 | C12—C11—C10 | 119.23 (18) |
C1—C2—H2 | 119.3 | C13—C12—C11 | 120.2 (2) |
C2—C3—C4 | 121.07 (18) | C13—C12—H12 | 119.9 |
C2—C3—H3 | 119.5 | C11—C12—H12 | 119.9 |
C4—C3—H3 | 119.5 | C12—C13—C14 | 120.9 (2) |
C3—C4—C5 | 117.60 (18) | C12—C13—H13 | 119.5 |
C3—C4—C7 | 120.50 (16) | C14—C13—H13 | 119.5 |
C5—C4—C7 | 121.87 (17) | C15—C14—C13 | 120.5 (2) |
C6—C5—C4 | 120.90 (19) | C15—C14—H14 | 119.8 |
C6—C5—H5 | 119.6 | C13—C14—H14 | 119.8 |
C4—C5—H5 | 119.6 | C14—C15—C10 | 120.7 (2) |
C5—C6—C1 | 121.37 (18) | C14—C15—H15 | 119.6 |
C5—C6—H6 | 119.3 | C10—C15—H15 | 119.6 |
C1—C6—H6 | 119.3 | O2—C16—O1 | 124.26 (18) |
N1—C7—C8 | 121.25 (18) | O2—C16—C9 | 122.20 (17) |
N1—C7—C4 | 118.09 (16) | O1—C16—C9 | 113.53 (17) |
C8—C7—C4 | 120.65 (17) | C1—C17—H17A | 109.5 |
C9—C8—C7 | 121.01 (18) | C1—C17—H17B | 109.5 |
C9—C8—H8 | 119.5 | H17A—C17—H17B | 109.5 |
C7—C8—H8 | 119.5 | C1—C17—H17C | 109.5 |
C8—C9—C10 | 119.15 (16) | H17A—C17—H17C | 109.5 |
C8—C9—C16 | 117.55 (17) | H17B—C17—H17C | 109.5 |
C6—C1—C2—C3 | 1.9 (3) | C16—C9—C10—C15 | 1.2 (3) |
C17—C1—C2—C3 | −178.5 (2) | C8—C9—C10—C11 | 0.2 (3) |
C1—C2—C3—C4 | −0.9 (3) | C16—C9—C10—C11 | −179.99 (19) |
C2—C3—C4—C5 | −0.6 (3) | C7—N1—C11—C12 | −178.7 (2) |
C2—C3—C4—C7 | 177.28 (18) | C7—N1—C11—C10 | 1.6 (3) |
C3—C4—C5—C6 | 1.1 (3) | C15—C10—C11—N1 | 177.7 (2) |
C7—C4—C5—C6 | −176.78 (19) | C9—C10—C11—N1 | −1.2 (3) |
C4—C5—C6—C1 | −0.1 (3) | C15—C10—C11—C12 | −2.0 (3) |
C2—C1—C6—C5 | −1.4 (3) | C9—C10—C11—C12 | 179.1 (2) |
C17—C1—C6—C5 | 179.0 (2) | N1—C11—C12—C13 | −179.1 (2) |
C11—N1—C7—C8 | −0.9 (3) | C10—C11—C12—C13 | 0.6 (4) |
C11—N1—C7—C4 | 179.92 (17) | C11—C12—C13—C14 | 1.0 (4) |
C3—C4—C7—N1 | −25.0 (3) | C12—C13—C14—C15 | −1.2 (4) |
C5—C4—C7—N1 | 152.79 (19) | C13—C14—C15—C10 | −0.3 (4) |
C3—C4—C7—C8 | 155.78 (19) | C11—C10—C15—C14 | 1.9 (4) |
C5—C4—C7—C8 | −26.4 (3) | C9—C10—C15—C14 | −179.3 (2) |
N1—C7—C8—C9 | −0.1 (3) | C8—C9—C16—O2 | 44.3 (3) |
C4—C7—C8—C9 | 179.09 (18) | C10—C9—C16—O2 | −135.5 (2) |
C7—C8—C9—C10 | 0.4 (3) | C8—C9—C16—O1 | −134.5 (2) |
C7—C8—C9—C16 | −179.40 (18) | C10—C9—C16—O1 | 45.7 (3) |
C8—C9—C10—C15 | −178.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1i | 0.89 (3) | 1.89 (3) | 2.763 (2) | 168 (2) |
C3—H3···O1ii | 0.93 | 2.51 | 3.233 (2) | 135 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C17H13NO2 |
Mr | 263.28 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 291 |
a, b, c (Å) | 4.1001 (6), 15.3464 (11), 20.3037 (17) |
β (°) | 90.859 (9) |
V (Å3) | 1277.4 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.70 × 0.08 × 0.05 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur Eos |
Absorption correction | Analytical [CrysAlis PRO (Oxford Diffraction, 2009), based on expressions derived from Clark & Reid (1995)] |
Tmin, Tmax | 0.992, 0.999 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4867, 2238, 1747 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.126, 1.04 |
No. of reflections | 2238 |
No. of parameters | 186 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.20, −0.24 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1i | 0.89 (3) | 1.89 (3) | 2.763 (2) | 168 (2) |
C3—H3···O1ii | 0.93 | 2.51 | 3.233 (2) | 135 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2. |
Acknowledgements
This work was carried out during sabbatical leave granted to MAK during the academic year 2011–2012.
References
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Quinoline derivatives are widely used as synthons for biologically important compounds (Tseng et al., 2008), (Kravchenko et al., 2005). In our group this moiety was used to synthesize new antitumor as well as antibacterial agents. The title molecule is shown in Fig. 1 with the numbering scheme. The dihedral angle between the plane of the carboxyl group and the quinoline mean plane is 45.05 (13)° and that between the toluene ring mean plane and the quinoline mean plane is 25.29 (7)°. The total puckering amplitude, Q, (Cremer & Pople, 1975) for the quinoline ring in the title compound is 0.044 (2)Å in the title compound as compared with the value of 0.080 (3) Å in the closely related compound 2-phenylquinoline-4-carboxlic acid (Blackburn et al., 1996). There is a hydrogen bond between the carboxylic acid oxygen atom, O1 and N1 in the quinoline ring, Table 1, Figure 2. In addition the molecules are linked by a weak C-H..O interaction between C3 and O1, Table 1. There is π–π stacking between molecules Molecules are stacked above and below one another with unit translation along the a-axis so that rings containing N1 stack above those containing N1, the same applies to the rings containing C1 and C12. This results in π–π stacking between the molecules: i) between rings containing N1 (centroid Cg1) [Cg1···Cg1(-1+x, y, z), centroid to centroid distance: 4.1001 (13) Å, perpendicular distance between rings: 3.7681 (8) Å slippage: 1.616Å] and ii) between rings containing C1, (centroid Cg2), [Cg2···Cg2(-1+x ,y, z), centroid to centroid distance 4.1000 (14) Å, perpendicular distance between rings 3.3521 (8) Å, slippage 2.361Å] and iii) between rings containing C12 (centroid Cg3) Cg3···Cg3 (-1+x, y, z), [centroid to centroid) distance 4.1003 (17) Å, perpendicular distance between rings 3.7411 (11)Å, slippage 1.678Å].