Literature DB >> 24454268

3,4-Di-methyl-phenyl quinoline-2-carboxyl-ate.

E Fazal1, Manpreet Kaur2, B S Sudha1, S Nagarajan3, Jerry P Jasinski4.   

Abstract

In the title compound, C18H15NO2, the dihedral angle between the mean planes of the quinoline ring system and the phenyl ring is 48.1 (5)°. The mean plane of the carboxyl-ate group is twisted from the mean planes of the latter by 19.8 (8) and 64.9 (5)°, respectively. The crystal packing features weak C-H⋯O inter-actions, which form chains along [010].

Entities:  

Year:  2013        PMID： 24454268      PMCID： PMC3885092          DOI： 10.1107/S1600536813032157

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For heterocycles in natural products, see: Morimoto et al. (1991 ▶); Michael (1997 ▶). For heterocycles in fragrances and dyes, see: Padwa et al. (1999 ▶). For heterocycles in biologically active compounds, see: Markees et al. (1970 ▶); Campbell et al. (1988 ▶). For the use of quinoline alkaloids as drugs for the treatment of malaria, see: Robert & Meunier (1998 ▶). For quinoline as a privileged scaffold in cancer drug discovery, see: Solomon & Lee (2011 ▶). For related structures, see: Fazal et al. (2012 ▶); Butcher et al. (2007 ▶); Jing & Qin (2008 ▶); Jasinski et al. (2010 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H15NO2 M = 277.32 Monoclinic, a = 6.19172 (17) Å b = 15.4196 (4) Å c = 14.6585 (4) Å β = 90.761 (3)° V = 1399.38 (7) Å3 Z = 4 Cu Kα radiation μ = 0.69 mm−1 T = 173 K 0.44 × 0.22 × 0.16 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.921, T max = 1.000 8355 measured reflections 2740 independent reflections 2387 reflections with I > 2σ(I) R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.042 wR(F 2) = 0.121 S = 1.05 2740 reflections 193 parameters H-atom parameters constrained Δρmax = 0.28 e Å−3 Δρmin = −0.24 e Å−3 Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: 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. Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813032157/qm2101sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032157/qm2101Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813032157/qm2101Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C18H15NO2F(000) = 608
Mr = 277.32Dx = 1.316 Mg m−3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 6.19172 (17) ÅCell parameters from 6294 reflections
b = 15.4196 (4) Åθ = 4.7–72.3°
c = 14.6585 (4) ŵ = 0.69 mm−1
β = 90.761 (3)°T = 173 K
V = 1399.38 (7) Å3Irregular, clear red
Z = 40.44 × 0.22 × 0.16 mm
Agilent Xcalibur (Eos, Gemini) diffractometer2740 independent reflections
Radiation source: Enhance (Cu) X-ray Source2387 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1Rint = 0.042
ω scansθmax = 72.3°, θmin = 4.2°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)h = −7→6
Tmin = 0.921, Tmax = 1.000k = −18→19
8355 measured reflectionsl = −14→18
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.042w = 1/[σ2(Fo2) + (0.0716P)2 + 0.1805P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.121(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.28 e Å−3
2740 reflectionsΔρmin = −0.24 e Å−3
193 parametersExtinction correction: SHELXL2012 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0048 (6)
Primary atom site location: structure-invariant direct methods
Experimental. 1H NMR(500 MHz,DMSO) δ 8.66 (1H,d, J= 8.5Hz), 8.26(1H,d, J= 8.5Hz),8.24(1H,d, J= 8.5 Hz), 8.15(1H,d, J= 8.03 Hz),7.93(1H,dt, J1= 8.2Hz, J2=6.46, J3=1.08Hz), 7.8(1H,t, J= 7.5Hz), 7.25(1H,d, J= 8.2Hz), 7.14(1H,d, J= 2.15Hz), 7.06(1H,dd, J1= 8.03Hz,J2=2.35),2.28(3H,s),2.25(3H,s).
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.
xyzUiso*/Ueq
O10.03672 (17)0.48206 (6)0.20779 (8)0.0457 (3)
O20.26816 (14)0.53658 (5)0.10569 (6)0.0302 (2)
N10.23607 (16)0.32280 (7)0.18546 (7)0.0247 (2)
C10.19203 (19)0.47407 (8)0.16176 (8)0.0269 (3)
C20.33036 (19)0.39405 (8)0.15562 (8)0.0247 (3)
C30.54041 (19)0.39753 (8)0.11950 (8)0.0286 (3)
H30.59960.45000.10100.034*
C40.65466 (19)0.32226 (8)0.11227 (8)0.0287 (3)
H40.79450.32290.08990.034*
C50.55877 (19)0.24325 (8)0.13906 (8)0.0258 (3)
C60.6605 (2)0.16151 (9)0.12935 (9)0.0315 (3)
H60.79760.15830.10440.038*
C70.5586 (2)0.08740 (9)0.15634 (9)0.0358 (3)
H70.62580.03400.14870.043*
C80.3518 (2)0.09127 (8)0.19569 (9)0.0339 (3)
H80.28520.04040.21460.041*
C90.2485 (2)0.16894 (8)0.20625 (9)0.0284 (3)
H90.11290.17070.23280.034*
C100.34768 (19)0.24685 (8)0.17682 (8)0.0240 (3)
C120.26169 (19)0.69008 (8)0.12548 (8)0.0254 (3)
H120.39950.68630.15120.031*
C130.1647 (2)0.77085 (8)0.11323 (8)0.0263 (3)
C14−0.0431 (2)0.77561 (8)0.07407 (8)0.0280 (3)
C15−0.1486 (2)0.69903 (9)0.04954 (8)0.0296 (3)
H15−0.28700.70200.02430.036*
C16−0.0521 (2)0.61829 (8)0.06192 (8)0.0287 (3)
H16−0.12400.56760.04530.034*
C170.1535 (2)0.61561 (8)0.09951 (8)0.0257 (3)
C180.2807 (2)0.85201 (9)0.14296 (10)0.0362 (3)
H18A0.41970.83700.16810.054*
H18B0.19740.88130.18840.054*
H18C0.29890.88950.09130.054*
C19−0.1517 (2)0.86210 (9)0.05940 (10)0.0402 (3)
H19A−0.17320.88970.11730.060*
H19B−0.28880.85350.02940.060*
H19C−0.06220.89810.02220.060*
U11U22U33U12U13U23
O10.0474 (6)0.0355 (5)0.0550 (7)0.0099 (4)0.0268 (5)0.0120 (4)
O20.0339 (5)0.0233 (5)0.0335 (5)0.0028 (3)0.0083 (4)0.0041 (3)
N10.0242 (5)0.0260 (5)0.0240 (5)−0.0007 (4)0.0019 (4)0.0017 (4)
C10.0291 (6)0.0257 (6)0.0258 (6)−0.0021 (5)0.0025 (5)0.0001 (5)
C20.0269 (6)0.0256 (6)0.0215 (6)−0.0014 (4)0.0000 (4)0.0012 (4)
C30.0282 (6)0.0287 (6)0.0290 (6)−0.0052 (5)0.0021 (5)0.0046 (5)
C40.0223 (6)0.0356 (7)0.0282 (6)−0.0012 (5)0.0040 (5)0.0033 (5)
C50.0259 (6)0.0295 (6)0.0221 (6)0.0010 (5)−0.0008 (4)0.0010 (4)
C60.0290 (6)0.0362 (7)0.0293 (6)0.0059 (5)0.0024 (5)0.0002 (5)
C70.0438 (8)0.0273 (7)0.0362 (7)0.0085 (5)−0.0010 (6)−0.0010 (5)
C80.0420 (7)0.0246 (6)0.0352 (7)−0.0038 (5)−0.0012 (6)0.0027 (5)
C90.0276 (6)0.0290 (6)0.0288 (6)−0.0035 (5)0.0019 (5)0.0021 (5)
C100.0250 (6)0.0256 (6)0.0214 (6)−0.0004 (4)−0.0007 (4)0.0010 (4)
C120.0253 (6)0.0283 (6)0.0228 (6)0.0005 (5)0.0009 (5)0.0003 (4)
C130.0314 (6)0.0255 (6)0.0221 (6)−0.0004 (5)0.0041 (5)−0.0012 (4)
C140.0306 (6)0.0304 (6)0.0230 (6)0.0058 (5)0.0047 (5)0.0006 (5)
C150.0249 (6)0.0390 (7)0.0250 (6)0.0009 (5)0.0004 (5)0.0012 (5)
C160.0316 (6)0.0290 (6)0.0255 (6)−0.0064 (5)0.0026 (5)−0.0012 (5)
C170.0304 (6)0.0237 (6)0.0231 (6)0.0022 (4)0.0058 (5)0.0016 (4)
C180.0433 (8)0.0278 (7)0.0374 (7)−0.0023 (5)−0.0016 (6)−0.0038 (5)
C190.0420 (8)0.0372 (8)0.0415 (8)0.0129 (6)0.0024 (6)0.0027 (6)
O1—C11.1885 (15)C9—H90.9300
O2—C11.3554 (14)C9—C101.4191 (16)
O2—C171.4127 (14)C12—H120.9300
N1—C21.3214 (15)C12—C131.3933 (17)
N1—C101.3665 (15)C12—C171.3806 (17)
C1—C21.5053 (16)C13—C141.4039 (18)
C2—C31.4118 (17)C13—C181.5045 (17)
C3—H30.9300C14—C151.3943 (18)
C3—C41.3640 (17)C14—C191.5077 (17)
C4—H40.9300C15—H150.9300
C4—C51.4132 (17)C15—C161.3918 (18)
C5—C61.4170 (17)C16—H160.9300
C5—C101.4272 (17)C16—C171.3809 (18)
C6—H60.9300C18—H18A0.9600
C6—C71.3666 (19)C18—H18B0.9600
C7—H70.9300C18—H18C0.9600
C7—C81.4122 (19)C19—H19A0.9600
C8—H80.9300C19—H19B0.9600
C8—C91.3676 (18)C19—H19C0.9600
C1—O2—C17118.28 (9)C9—C10—C5119.16 (11)
C2—N1—C10117.11 (10)C13—C12—H12120.0
O1—C1—O2124.13 (11)C17—C12—H12120.0
O1—C1—C2125.75 (11)C17—C12—C13120.08 (11)
O2—C1—C2110.12 (10)C12—C13—C14119.38 (11)
N1—C2—C1114.05 (10)C12—C13—C18120.20 (11)
N1—C2—C3124.68 (11)C14—C13—C18120.42 (11)
C3—C2—C1121.26 (10)C13—C14—C19120.60 (12)
C2—C3—H3120.7C15—C14—C13119.01 (11)
C4—C3—C2118.56 (11)C15—C14—C19120.39 (12)
C4—C3—H3120.7C14—C15—H15119.2
C3—C4—H4120.3C16—C15—C14121.67 (11)
C3—C4—C5119.46 (11)C16—C15—H15119.2
C5—C4—H4120.3C15—C16—H16121.0
C4—C5—C6123.37 (11)C17—C16—C15118.08 (11)
C4—C5—C10117.68 (11)C17—C16—H16121.0
C6—C5—C10118.95 (11)C12—C17—O2117.27 (11)
C5—C6—H6119.8C12—C17—C16121.77 (11)
C7—C6—C5120.48 (12)C16—C17—O2120.75 (11)
C7—C6—H6119.8C13—C18—H18A109.5
C6—C7—H7119.7C13—C18—H18B109.5
C6—C7—C8120.50 (12)C13—C18—H18C109.5
C8—C7—H7119.7H18A—C18—H18B109.5
C7—C8—H8119.6H18A—C18—H18C109.5
C9—C8—C7120.74 (12)H18B—C18—H18C109.5
C9—C8—H8119.6C14—C19—H19A109.5
C8—C9—H9119.9C14—C19—H19B109.5
C8—C9—C10120.13 (11)C14—C19—H19C109.5
C10—C9—H9119.9H19A—C19—H19B109.5
N1—C10—C5122.42 (10)H19A—C19—H19C109.5
N1—C10—C9118.42 (11)H19B—C19—H19C109.5
O1—C1—C2—N118.18 (18)C8—C9—C10—N1177.64 (11)
O1—C1—C2—C3−162.66 (13)C8—C9—C10—C5−2.07 (18)
O2—C1—C2—N1−160.96 (10)C10—N1—C2—C1176.20 (10)
O2—C1—C2—C318.20 (16)C10—N1—C2—C3−2.92 (18)
N1—C2—C3—C41.69 (19)C10—C5—C6—C7−0.47 (19)
C1—O2—C17—C12118.93 (12)C12—C13—C14—C150.89 (18)
C1—O2—C17—C16−66.23 (14)C12—C13—C14—C19−179.61 (11)
C1—C2—C3—C4−177.37 (11)C13—C12—C17—O2174.15 (10)
C2—N1—C10—C51.18 (17)C13—C12—C17—C16−0.63 (18)
C2—N1—C10—C9−178.52 (11)C13—C14—C15—C16−0.78 (18)
C2—C3—C4—C51.36 (18)C14—C15—C16—C17−0.04 (18)
C3—C4—C5—C6176.44 (12)C15—C16—C17—O2−173.85 (10)
C3—C4—C5—C10−2.87 (18)C15—C16—C17—C120.75 (18)
C4—C5—C6—C7−179.76 (12)C17—O2—C1—O1−1.63 (18)
C4—C5—C10—N11.64 (18)C17—O2—C1—C2177.53 (10)
C4—C5—C10—C9−178.66 (11)C17—C12—C13—C14−0.21 (18)
C5—C6—C7—C8−1.0 (2)C17—C12—C13—C18178.94 (11)
C6—C5—C10—N1−177.69 (11)C18—C13—C14—C15−178.26 (11)
C6—C5—C10—C92.00 (18)C18—C13—C14—C191.24 (18)
C6—C7—C8—C91.0 (2)C19—C14—C15—C16179.73 (11)
C7—C8—C9—C100.58 (19)
D—H···AD—HH···AD···AD—H···A
C8—H8···O1i0.932.483.2735 (16)144
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C8—H8⋯O1i 0.932.483.2735 (16)144

Symmetry code: (i) .

  6 in total

Review 1.  Quinoline as a privileged scaffold in cancer drug discovery.

Authors:  V R Solomon; H Lee
Journal:  Curr Med Chem       Date:  2011       Impact factor: 4.530

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  Antiprotozoal 4-aryloxy-2-aminoquinolines and related compounds.

Authors:  D G Markees; V C Dewey; G W Kidder
Journal:  J Med Chem       Date:  1970-03       Impact factor: 7.446

4.  A Cycloaddition Approach toward the Synthesis of Substituted Indolines and Tetrahydroquinolines.

Authors:  Albert Padwa; Michael A. Brodney; Bing Liu; Kyosuke Satake; Tianhua Wu
Journal:  J Org Chem       Date:  1999-05-14       Impact factor: 4.354

5.  2,4-Diamino-6,7-dimethoxyquinoline derivatives as alpha 1-adrenoceptor antagonists and antihypertensive agents.

Authors:  S F Campbell; J D Hardstone; M J Palmer
Journal:  J Med Chem       Date:  1988-05       Impact factor: 7.446

6.  4-Methyl-phenyl quinoline-2-carboxyl-ate.

Authors:  E Fazal; Jerry P Jasinski; Shannon T Krauss; B S Sudha; H S Yathirajan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-10-27
  6 in total
  1 in total

1.  2-Isopropyl-5-methyl-cyclo-hexyl quinoline-2-carboxyl-ate.

Authors:  E Fazal; Jerry P Jasinski; Brian J Anderson; B S Sudha; S Nagarajan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-12-11
  1 in total

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