organic compounds
2,5-Dimethylphenyl quinoline-2-carboxylate
aDepartment of Chemistry, Yuvaraja's College, Mysore 570 005, India, bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, cDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and dP.P.S.F.T. Department, Central Food Technplogy Research institute, Mysore 570 005, India
*Correspondence e-mail: jjasinski@keene.edu
In the title compound, C18H15NO2, the dihedral angle between the mean planes of the quinoline ring system and the phenyl ring is 78.8 (1)°. The mean plane of the carboxylate group is twisted from the mean planes of the quinoline ring system and phenyl ring by 1.5 (9) and 77.6 (4)°, respectively. In the crystal, molecules are linked by weak C—H⋯O interactions, generating C(8) chains along [001]. Weak π–π stacking interactions are also observed [centroid–centroid separation = 3.6238 (12) Å].
CCDC reference: 980675
Related literature
For related structures and background to quinoline derivatives, see: Fazal et al. (2014); Jasinski et al. (2010).
Experimental
Crystal data
|
Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2.
Supporting information
CCDC reference: 980675
10.1107/S160053681400052X/hb7183sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681400052X/hb7183Isup2.hkl
Supporting information file. DOI: 10.1107/S160053681400052X/hb7183Isup3.cml
To a mixture of 1.73 g (10 mmole) of quinaldic acid and 1.56 g (10 mmole) of 2,5-dimethylphenol in a round-bottomed flask fitted with a reflux condenser with a drying tube was added 0.15 g (10 mmole) of phosphorous oxychloride. The mixture was heated with occasional swirling, and temperature maintained at 348-353 K. At the end of eight hours the reaction mixture was poured in to a solution of 2 g of sodium bicarbonate in 25 ml of water. The precipitated ester was collected on a filter and washed with water. The yield of crude, air dried 2,5-dimethylphenyl quinoline-2-carboxylate was 1.71 to 1.85 g (65-70 %). Irregular colourless chunks were obtained by recrystallization from absolute ethanol solution by slow evaporation.
All of the H atoms were placed in their calculated positions and then refined using the riding model with Atom—H lengths of 0.95Å (CH) or 0.98Å (CH3). Isotropic displacement parameters for these atoms were set to 1.2 (CH) or 1.5 (CH3) times Ueq of the parent atom. Idealised Me refined as rotating group.
Following our recent report on 2-isopropyl-5-methylcyclohexyl quinoline-2-carboxylate (Fazal et al., 2014), we now describe the
of the title compound, (I), The synthesis, crystal structures and theoretical studies of four derived from 4-hydrazinyl-8-(trifluoromethyl) quinoline (Jasinski et al., 2010) have also been reported.The dihedral angle between the mean planes of the quinoline ring and the phenyl ring is 78.8 (1)° (Fig. 1). The mean plane of the carboxylate group is twisted from the mean planes of the quinoline ring and phenyl ring by 1.5 (9)° and 77.6 (4)°, respectively. The crystal packing is influenced by weak C17—H17B···O1 interactions making chains along [0 0 1](Fig. 2). In addition, weak Cg2–Cg3 π–π interactions are observed (Cg2–Cg3 = 3.6238 (12)Å; Cg2 = C5–C10; Cg3 = C11–C16; 1/2 + x, 1/2 - y, 1 - z).
For related structures and background to quinoline derivatives, see: Fazal et al. (2014); Jasinski et al. (2010).
Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).C18H15NO2 | Dx = 1.324 Mg m−3 |
Mr = 277.31 | Cu Kα radiation, λ = 1.54184 Å |
Orthorhombic, P212121 | Cell parameters from 3982 reflections |
a = 8.2261 (3) Å | θ = 3.0–72.4° |
b = 11.6007 (5) Å | µ = 0.69 mm−1 |
c = 14.5738 (5) Å | T = 173 K |
V = 1390.76 (9) Å3 | Irregular, colourless |
Z = 4 | 0.46 × 0.34 × 0.18 mm |
F(000) = 584 |
Agilent Gemini EOS diffractometer | 2721 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 2585 reflections with I > 2σ(I) |
Detector resolution: 16.0416 pixels mm-1 | Rint = 0.031 |
ω scans | θmax = 72.6°, θmin = 4.9° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | h = −6→10 |
Tmin = 0.711, Tmax = 1.000 | k = −14→13 |
8332 measured reflections | l = −17→17 |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0609P)2 + 0.1748P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.035 | (Δ/σ)max = 0.008 |
wR(F2) = 0.101 | Δρmax = 0.18 e Å−3 |
S = 1.05 | Δρmin = −0.16 e Å−3 |
2721 reflections | Extinction correction: SHELXL2012 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
193 parameters | Extinction coefficient: 0.0027 (7) |
0 restraints | Absolute structure: Flack parameter determined using 1049 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.04 (16) |
Hydrogen site location: inferred from neighbouring sites |
C18H15NO2 | V = 1390.76 (9) Å3 |
Mr = 277.31 | Z = 4 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 8.2261 (3) Å | µ = 0.69 mm−1 |
b = 11.6007 (5) Å | T = 173 K |
c = 14.5738 (5) Å | 0.46 × 0.34 × 0.18 mm |
Agilent Gemini EOS diffractometer | 2721 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | 2585 reflections with I > 2σ(I) |
Tmin = 0.711, Tmax = 1.000 | Rint = 0.031 |
8332 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.101 | Δρmax = 0.18 e Å−3 |
S = 1.05 | Δρmin = −0.16 e Å−3 |
2721 reflections | Absolute structure: Flack parameter determined using 1049 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
193 parameters | Absolute structure parameter: −0.04 (16) |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.4090 (2) | 0.00776 (14) | 0.45505 (11) | 0.0439 (4) | |
O2 | 0.5803 (2) | 0.13777 (12) | 0.39481 (9) | 0.0330 (4) | |
N1 | 0.3984 (2) | 0.13265 (14) | 0.61466 (11) | 0.0259 (4) | |
C1 | 0.4863 (2) | 0.09441 (16) | 0.46254 (13) | 0.0274 (4) | |
C2 | 0.4902 (2) | 0.16990 (15) | 0.54669 (12) | 0.0248 (4) | |
C3 | 0.5847 (2) | 0.27162 (16) | 0.54988 (13) | 0.0276 (4) | |
H3 | 0.6468 | 0.2956 | 0.4984 | 0.033* | |
C4 | 0.5840 (3) | 0.33438 (17) | 0.62920 (14) | 0.0292 (4) | |
H4 | 0.6464 | 0.4031 | 0.6334 | 0.035* | |
C5 | 0.4907 (3) | 0.29728 (16) | 0.70485 (13) | 0.0265 (4) | |
C6 | 0.4872 (3) | 0.35546 (17) | 0.79056 (14) | 0.0321 (4) | |
H6 | 0.5502 | 0.4232 | 0.7992 | 0.038* | |
C7 | 0.3934 (3) | 0.31404 (19) | 0.86066 (14) | 0.0349 (5) | |
H7 | 0.3927 | 0.3529 | 0.9180 | 0.042* | |
C8 | 0.2979 (3) | 0.21456 (19) | 0.84884 (14) | 0.0334 (5) | |
H8 | 0.2323 | 0.1877 | 0.8981 | 0.040* | |
C9 | 0.2982 (3) | 0.15600 (17) | 0.76741 (14) | 0.0296 (4) | |
H9 | 0.2325 | 0.0893 | 0.7601 | 0.035* | |
C10 | 0.3968 (2) | 0.19518 (16) | 0.69387 (13) | 0.0252 (4) | |
C11 | 0.5828 (2) | 0.07494 (17) | 0.31151 (12) | 0.0271 (4) | |
C12 | 0.6794 (2) | −0.02221 (17) | 0.30398 (14) | 0.0286 (4) | |
C13 | 0.6803 (3) | −0.07618 (18) | 0.21885 (14) | 0.0318 (4) | |
H13 | 0.7445 | −0.1435 | 0.2107 | 0.038* | |
C14 | 0.5903 (3) | −0.03456 (18) | 0.14550 (14) | 0.0326 (5) | |
H14 | 0.5932 | −0.0740 | 0.0884 | 0.039* | |
C15 | 0.4960 (2) | 0.06388 (18) | 0.15446 (13) | 0.0313 (4) | |
C16 | 0.4932 (3) | 0.11850 (17) | 0.23933 (14) | 0.0294 (4) | |
H16 | 0.4294 | 0.1860 | 0.2477 | 0.035* | |
C17 | 0.4019 (3) | 0.1117 (2) | 0.07440 (16) | 0.0452 (6) | |
H17A | 0.3427 | 0.1809 | 0.0938 | 0.068* | |
H17B | 0.3245 | 0.0537 | 0.0525 | 0.068* | |
H17C | 0.4772 | 0.1318 | 0.0248 | 0.068* | |
C18 | 0.7792 (3) | −0.0662 (2) | 0.38316 (16) | 0.0400 (5) | |
H18A | 0.8297 | −0.0011 | 0.4151 | 0.060* | |
H18B | 0.8640 | −0.1180 | 0.3601 | 0.060* | |
H18C | 0.7088 | −0.1083 | 0.4258 | 0.060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0543 (10) | 0.0445 (9) | 0.0330 (8) | −0.0212 (8) | 0.0128 (8) | −0.0122 (7) |
O2 | 0.0444 (8) | 0.0311 (7) | 0.0235 (7) | −0.0073 (6) | 0.0076 (6) | −0.0061 (5) |
N1 | 0.0281 (8) | 0.0265 (8) | 0.0232 (8) | 0.0012 (7) | 0.0003 (7) | −0.0005 (6) |
C1 | 0.0283 (9) | 0.0294 (9) | 0.0246 (9) | −0.0001 (8) | 0.0006 (8) | −0.0011 (7) |
C2 | 0.0270 (8) | 0.0262 (9) | 0.0211 (8) | 0.0032 (8) | −0.0015 (8) | −0.0008 (7) |
C3 | 0.0305 (9) | 0.0273 (9) | 0.0251 (9) | 0.0009 (8) | 0.0008 (8) | 0.0019 (7) |
C4 | 0.0327 (9) | 0.0237 (9) | 0.0311 (10) | −0.0010 (8) | −0.0015 (8) | −0.0002 (8) |
C5 | 0.0308 (9) | 0.0238 (9) | 0.0248 (9) | 0.0061 (8) | −0.0032 (8) | −0.0015 (7) |
C6 | 0.0415 (11) | 0.0251 (9) | 0.0296 (10) | 0.0033 (9) | −0.0039 (9) | −0.0041 (7) |
C7 | 0.0453 (11) | 0.0359 (11) | 0.0234 (9) | 0.0113 (10) | −0.0012 (9) | −0.0056 (8) |
C8 | 0.0372 (10) | 0.0397 (11) | 0.0232 (9) | 0.0093 (9) | 0.0029 (9) | 0.0028 (8) |
C9 | 0.0302 (9) | 0.0321 (10) | 0.0264 (10) | 0.0025 (8) | −0.0001 (8) | 0.0021 (8) |
C10 | 0.0269 (9) | 0.0255 (9) | 0.0234 (8) | 0.0052 (8) | −0.0015 (7) | 0.0004 (7) |
C11 | 0.0336 (10) | 0.0254 (9) | 0.0222 (8) | −0.0067 (8) | 0.0048 (8) | −0.0033 (7) |
C12 | 0.0289 (9) | 0.0281 (9) | 0.0288 (10) | −0.0035 (8) | 0.0038 (8) | 0.0017 (8) |
C13 | 0.0338 (10) | 0.0272 (9) | 0.0344 (10) | −0.0004 (9) | 0.0087 (9) | −0.0026 (8) |
C14 | 0.0377 (10) | 0.0345 (11) | 0.0256 (9) | −0.0093 (9) | 0.0046 (9) | −0.0091 (8) |
C15 | 0.0300 (9) | 0.0375 (10) | 0.0263 (9) | −0.0080 (9) | 0.0015 (9) | 0.0012 (8) |
C16 | 0.0316 (9) | 0.0271 (9) | 0.0296 (10) | 0.0012 (9) | 0.0056 (8) | 0.0005 (7) |
C17 | 0.0443 (12) | 0.0608 (15) | 0.0306 (11) | −0.0007 (12) | −0.0047 (10) | 0.0035 (10) |
C18 | 0.0411 (12) | 0.0450 (12) | 0.0338 (11) | 0.0028 (10) | 0.0004 (10) | 0.0049 (10) |
O1—C1 | 1.194 (2) | C9—H9 | 0.9500 |
O2—C1 | 1.351 (2) | C9—C10 | 1.419 (3) |
O2—C11 | 1.416 (2) | C11—C12 | 1.383 (3) |
N1—C2 | 1.319 (2) | C11—C16 | 1.380 (3) |
N1—C10 | 1.363 (2) | C12—C13 | 1.390 (3) |
C1—C2 | 1.507 (2) | C12—C18 | 1.505 (3) |
C2—C3 | 1.414 (3) | C13—H13 | 0.9500 |
C3—H3 | 0.9500 | C13—C14 | 1.387 (3) |
C3—C4 | 1.366 (3) | C14—H14 | 0.9500 |
C4—H4 | 0.9500 | C14—C15 | 1.387 (3) |
C4—C5 | 1.411 (3) | C15—C16 | 1.390 (3) |
C5—C6 | 1.420 (2) | C15—C17 | 1.507 (3) |
C5—C10 | 1.423 (3) | C16—H16 | 0.9500 |
C6—H6 | 0.9500 | C17—H17A | 0.9800 |
C6—C7 | 1.368 (3) | C17—H17B | 0.9800 |
C7—H7 | 0.9500 | C17—H17C | 0.9800 |
C7—C8 | 1.407 (3) | C18—H18A | 0.9800 |
C8—H8 | 0.9500 | C18—H18B | 0.9800 |
C8—C9 | 1.367 (3) | C18—H18C | 0.9800 |
C1—O2—C11 | 116.31 (15) | C9—C10—C5 | 119.47 (17) |
C2—N1—C10 | 117.84 (16) | C12—C11—O2 | 119.72 (17) |
O1—C1—O2 | 123.44 (18) | C16—C11—O2 | 117.19 (17) |
O1—C1—C2 | 125.08 (18) | C16—C11—C12 | 123.00 (17) |
O2—C1—C2 | 111.47 (16) | C11—C12—C13 | 116.18 (18) |
N1—C2—C1 | 114.13 (16) | C11—C12—C18 | 121.93 (18) |
N1—C2—C3 | 124.32 (17) | C13—C12—C18 | 121.89 (19) |
C3—C2—C1 | 121.55 (17) | C12—C13—H13 | 119.1 |
C2—C3—H3 | 121.0 | C14—C13—C12 | 121.88 (19) |
C4—C3—C2 | 118.05 (18) | C14—C13—H13 | 119.1 |
C4—C3—H3 | 121.0 | C13—C14—H14 | 119.6 |
C3—C4—H4 | 120.0 | C15—C14—C13 | 120.84 (18) |
C3—C4—C5 | 120.07 (18) | C15—C14—H14 | 119.6 |
C5—C4—H4 | 120.0 | C14—C15—C16 | 117.95 (19) |
C4—C5—C6 | 123.59 (18) | C14—C15—C17 | 121.20 (19) |
C4—C5—C10 | 117.47 (16) | C16—C15—C17 | 120.8 (2) |
C6—C5—C10 | 118.93 (17) | C11—C16—C15 | 120.15 (19) |
C5—C6—H6 | 120.0 | C11—C16—H16 | 119.9 |
C7—C6—C5 | 120.08 (19) | C15—C16—H16 | 119.9 |
C7—C6—H6 | 120.0 | C15—C17—H17A | 109.5 |
C6—C7—H7 | 119.6 | C15—C17—H17B | 109.5 |
C6—C7—C8 | 120.80 (18) | C15—C17—H17C | 109.5 |
C8—C7—H7 | 119.6 | H17A—C17—H17B | 109.5 |
C7—C8—H8 | 119.6 | H17A—C17—H17C | 109.5 |
C9—C8—C7 | 120.9 (2) | H17B—C17—H17C | 109.5 |
C9—C8—H8 | 119.6 | C12—C18—H18A | 109.5 |
C8—C9—H9 | 120.1 | C12—C18—H18B | 109.5 |
C8—C9—C10 | 119.82 (19) | C12—C18—H18C | 109.5 |
C10—C9—H9 | 120.1 | H18A—C18—H18B | 109.5 |
N1—C10—C5 | 122.21 (17) | H18A—C18—H18C | 109.5 |
N1—C10—C9 | 118.32 (17) | H18B—C18—H18C | 109.5 |
O1—C1—C2—N1 | −0.1 (3) | C6—C5—C10—C9 | 2.1 (3) |
O1—C1—C2—C3 | −179.8 (2) | C6—C7—C8—C9 | 0.9 (3) |
O2—C1—C2—N1 | 178.98 (16) | C7—C8—C9—C10 | 0.5 (3) |
O2—C1—C2—C3 | −0.7 (3) | C8—C9—C10—N1 | 177.87 (18) |
O2—C11—C12—C13 | −177.39 (17) | C8—C9—C10—C5 | −1.9 (3) |
O2—C11—C12—C18 | 2.0 (3) | C10—N1—C2—C1 | 179.07 (16) |
O2—C11—C16—C15 | 177.19 (17) | C10—N1—C2—C3 | −1.3 (3) |
N1—C2—C3—C4 | 1.5 (3) | C10—C5—C6—C7 | −0.8 (3) |
C1—O2—C11—C12 | −79.9 (2) | C11—O2—C1—O1 | 0.5 (3) |
C1—O2—C11—C16 | 103.4 (2) | C11—O2—C1—C2 | −178.63 (15) |
C1—C2—C3—C4 | −178.88 (17) | C11—C12—C13—C14 | 0.3 (3) |
C2—N1—C10—C5 | −0.3 (3) | C12—C11—C16—C15 | 0.6 (3) |
C2—N1—C10—C9 | 179.87 (17) | C12—C13—C14—C15 | 0.5 (3) |
C2—C3—C4—C5 | −0.1 (3) | C13—C14—C15—C16 | −0.8 (3) |
C3—C4—C5—C6 | 177.96 (18) | C13—C14—C15—C17 | 178.1 (2) |
C3—C4—C5—C10 | −1.4 (3) | C14—C15—C16—C11 | 0.2 (3) |
C4—C5—C6—C7 | 179.9 (2) | C16—C11—C12—C13 | −0.9 (3) |
C4—C5—C10—N1 | 1.6 (3) | C16—C11—C12—C18 | 178.5 (2) |
C4—C5—C10—C9 | −178.58 (18) | C17—C15—C16—C11 | −178.65 (19) |
C5—C6—C7—C8 | −0.7 (3) | C18—C12—C13—C14 | −179.00 (19) |
C6—C5—C10—N1 | −177.74 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17B···O1i | 0.98 | 2.49 | 3.389 (3) | 152 |
Symmetry code: (i) −x+1/2, −y, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17B···O1i | 0.98 | 2.49 | 3.389 (3) | 152 |
Symmetry code: (i) −x+1/2, −y, z−1/2. |
Acknowledgements
EF thanks the CFTRI, Mysore and Yuvaraja's College, UOM, for providing research facilities. EF is grateful to Mr J. R. Manjunatha, PPSFT, CFTRI for the NMR spectra. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.
References
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Following our recent report on 2-isopropyl-5-methylcyclohexyl quinoline-2-carboxylate (Fazal et al., 2014), we now describe the crystal structure of the title compound, (I), The synthesis, crystal structures and theoretical studies of four Schiff bases derived from 4-hydrazinyl-8-(trifluoromethyl) quinoline (Jasinski et al., 2010) have also been reported.
The dihedral angle between the mean planes of the quinoline ring and the phenyl ring is 78.8 (1)° (Fig. 1). The mean plane of the carboxylate group is twisted from the mean planes of the quinoline ring and phenyl ring by 1.5 (9)° and 77.6 (4)°, respectively. The crystal packing is influenced by weak C17—H17B···O1 interactions making chains along [0 0 1](Fig. 2). In addition, weak Cg2–Cg3 π–π interactions are observed (Cg2–Cg3 = 3.6238 (12)Å; Cg2 = C5–C10; Cg3 = C11–C16; 1/2 + x, 1/2 - y, 1 - z).