Literature DB >> 24454261

4-Chloro-3-methyl-phenyl quinoline-2-carboxyl-ate.

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

Abstract

In the title compound, C17H12ClNO2, the dihedral angle between the mean planes of the quinoline ring system and the benzene ring is 68.7 (7)°. The mean plane of the carboxyl-ate group is twisted from the latter planes by 14.0 (1) and 80.2 (4)°, respectively. In the crystal, weak C-H⋯O inter-actions are observed, forming chains along [001]. In addition, π-π stacking inter-actions [centroid-centroid distances = 3.8343 (13) and 3.7372 (13)Å] occur. No classical hydrogen bonds were observed.

Entities:  

Year:  2013        PMID： 24454261      PMCID： PMC3885085          DOI： 10.1107/S1600536813032017

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 efficient 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 ▶).

Experimental

Crystal data

C17H12ClNO2 M = 297.73 Orthorhombic, a = 7.75379 (16) Å b = 11.9658 (3) Å c = 14.9005 (3) Å V = 1382.48 (5) Å3 Z = 4 Cu Kα radiation μ = 2.48 mm−1 T = 173 K 0.32 × 0.24 × 0.20 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.530, T max = 1.000 8419 measured reflections 2703 independent reflections 2636 reflections with I > 2σ(I) R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.032 wR(F 2) = 0.085 S = 1.05 2703 reflections 192 parameters H-atom parameters constrained Δρmax = 0.20 e Å−3 Δρmin = −0.19 e Å−3 Absolute structure: Flack parameter determined using 1081 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▶) Absolute structure parameter: −0.009 (10) 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/S1600536813032017/bt6947sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032017/bt6947Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813032017/bt6947Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H12ClNO2Dx = 1.430 Mg m−3
Mr = 297.73Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121Cell parameters from 4795 reflections
a = 7.75379 (16) Åθ = 4.7–72.2°
b = 11.9658 (3) ŵ = 2.48 mm−1
c = 14.9005 (3) ÅT = 173 K
V = 1382.48 (5) Å3Irregular, colourless
Z = 40.32 × 0.24 × 0.20 mm
F(000) = 616
Agilent Xcalibur (Eos, Gemini) diffractometer2703 independent reflections
Radiation source: Enhance (Cu) X-ray Source2636 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1Rint = 0.030
ω scansθmax = 72.3°, θmin = 4.7°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)h = −9→4
Tmin = 0.530, Tmax = 1.000k = −14→14
8419 measured reflectionsl = −17→18
Refinement on F2H-atom parameters constrained
Least-squares matrix: fullw = 1/[σ2(Fo2) + (0.0574P)2 + 0.1134P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.032(Δ/σ)max < 0.001
wR(F2) = 0.085Δρmax = 0.20 e Å−3
S = 1.05Δρmin = −0.19 e Å−3
2703 reflectionsExtinction correction: SHELXL2012 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
192 parametersExtinction coefficient: 0.0036 (6)
0 restraintsAbsolute structure: Flack parameter determined using 1081 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: −0.009 (10)
Hydrogen site location: inferred from neighbouring sites
Experimental. 1HNMR(500 MHz,DMSO) δ 8.66 (1H,d, J= 8.51Hz), 8.27(1H,d, J= 8.5Hz),8.24(1H,d, J= 8.43 Hz), 8.15(1H,d, J= 8.2 Hz),7.93(1H,dt, J1= 8.07Hz, J2=6.73, J3=1.06Hz), 7.8(1H,t, J= 7.55Hz), 7.54(1H,d, J= 8.6Hz), 7.41(1H,d, J= 2.4Hz), 7.26(1H,dd, J1= 8.6Hz, J2=2.57 Hz), 3.3-3.4(1H,m),2.38(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
Cl10.64546 (8)−0.08068 (5)0.89548 (4)0.03791 (19)
O10.3575 (3)0.03286 (15)0.50511 (12)0.0448 (5)
O20.5593 (2)0.15377 (14)0.55202 (10)0.0319 (4)
N10.3627 (2)0.13829 (14)0.33957 (12)0.0241 (4)
C10.4441 (3)0.11335 (17)0.49220 (14)0.0262 (5)
C20.4431 (3)0.18389 (18)0.40823 (14)0.0244 (4)
C30.5281 (3)0.28841 (18)0.40610 (15)0.0271 (5)
H30.57870.31790.45750.032*
C40.5337 (3)0.34478 (19)0.32646 (16)0.0284 (5)
H40.58800.41400.32300.034*
C50.4568 (3)0.29779 (17)0.24938 (15)0.0244 (4)
C60.4651 (3)0.34833 (19)0.16312 (16)0.0305 (5)
H60.52190.41620.15570.037*
C70.3899 (3)0.2973 (2)0.09138 (16)0.0343 (5)
H70.39870.32960.03480.041*
C80.2985 (3)0.1955 (2)0.10181 (16)0.0324 (5)
H80.24670.16230.05230.039*
C90.2861 (3)0.14592 (19)0.18406 (15)0.0276 (5)
H90.22330.08020.19050.033*
C100.3685 (3)0.19422 (18)0.25977 (14)0.0231 (4)
C110.5754 (3)0.09412 (19)0.63323 (14)0.0270 (5)
C120.4958 (3)0.13691 (19)0.70842 (15)0.0259 (4)
H120.42950.20140.70390.031*
C130.5141 (3)0.08374 (19)0.79167 (14)0.0255 (4)
C140.6158 (3)−0.01188 (18)0.79341 (15)0.0265 (5)
C150.6979 (3)−0.05421 (19)0.71832 (16)0.0305 (5)
H150.7661−0.11790.72260.037*
C160.6771 (3)−0.00042 (19)0.63626 (15)0.0305 (5)
H160.7305−0.02750.58480.037*
C170.4262 (3)0.1281 (2)0.87402 (15)0.0340 (5)
H17A0.36640.19600.85940.051*
H17B0.51070.14300.91960.051*
H17C0.34520.07380.89570.051*
U11U22U33U12U13U23
Cl10.0486 (3)0.0340 (3)0.0312 (3)−0.0002 (3)−0.0084 (2)0.0109 (2)
O10.0585 (11)0.0405 (10)0.0356 (9)−0.0239 (9)−0.0172 (9)0.0143 (8)
O20.0431 (9)0.0316 (8)0.0209 (7)−0.0097 (7)−0.0046 (7)0.0033 (6)
N10.0279 (8)0.0201 (8)0.0241 (8)−0.0002 (8)−0.0002 (7)0.0010 (7)
C10.0301 (10)0.0250 (11)0.0235 (10)−0.0002 (9)−0.0018 (9)−0.0006 (8)
C20.0267 (10)0.0213 (9)0.0251 (10)0.0028 (8)0.0001 (8)0.0000 (8)
C30.0298 (11)0.0229 (10)0.0285 (11)−0.0003 (8)−0.0029 (9)−0.0029 (9)
C40.0299 (11)0.0193 (10)0.0360 (11)−0.0009 (8)0.0009 (9)0.0000 (9)
C50.0256 (10)0.0194 (9)0.0282 (10)0.0040 (8)0.0043 (8)0.0017 (8)
C60.0345 (12)0.0238 (11)0.0331 (11)0.0032 (9)0.0064 (9)0.0064 (9)
C70.0447 (14)0.0325 (12)0.0256 (11)0.0071 (10)0.0060 (10)0.0066 (9)
C80.0407 (12)0.0319 (12)0.0246 (10)0.0060 (9)−0.0007 (9)−0.0031 (9)
C90.0325 (10)0.0221 (10)0.0282 (11)0.0023 (9)−0.0002 (9)−0.0011 (9)
C100.0247 (10)0.0196 (9)0.0250 (10)0.0040 (8)0.0019 (8)0.0004 (8)
C110.0320 (10)0.0274 (11)0.0216 (10)−0.0082 (9)−0.0049 (8)0.0025 (8)
C120.0277 (10)0.0230 (10)0.0269 (10)−0.0016 (9)−0.0038 (8)0.0000 (9)
C130.0264 (10)0.0254 (10)0.0247 (10)−0.0047 (9)−0.0021 (8)−0.0009 (9)
C140.0310 (11)0.0249 (10)0.0236 (9)−0.0045 (9)−0.0060 (8)0.0041 (8)
C150.0338 (12)0.0222 (11)0.0354 (12)0.0004 (9)−0.0032 (9)−0.0025 (9)
C160.0352 (12)0.0299 (11)0.0263 (10)−0.0024 (9)0.0007 (9)−0.0070 (9)
C170.0378 (12)0.0375 (12)0.0268 (11)0.0003 (10)0.0050 (9)−0.0004 (9)
Cl1—C141.745 (2)C8—H80.9300
O1—C11.190 (3)C8—C91.365 (3)
O2—C11.352 (3)C9—H90.9300
O2—C111.410 (2)C9—C101.420 (3)
N1—C21.317 (3)C11—C121.378 (3)
N1—C101.365 (3)C11—C161.380 (3)
C1—C21.509 (3)C12—H120.9300
C2—C31.414 (3)C12—C131.401 (3)
C3—H30.9300C13—C141.390 (3)
C3—C41.366 (3)C13—C171.501 (3)
C4—H40.9300C14—C151.383 (3)
C4—C51.411 (3)C15—H150.9300
C5—C61.422 (3)C15—C161.391 (3)
C5—C101.424 (3)C16—H160.9300
C6—H60.9300C17—H17A0.9600
C6—C71.362 (4)C17—H17B0.9600
C7—H70.9300C17—H17C0.9600
C7—C81.418 (4)
C1—O2—C11116.31 (17)C10—C9—H9119.8
C2—N1—C10117.25 (18)N1—C10—C5122.49 (19)
O1—C1—O2123.8 (2)N1—C10—C9118.53 (19)
O1—C1—C2125.7 (2)C9—C10—C5119.0 (2)
O2—C1—C2110.48 (18)C12—C11—O2118.0 (2)
N1—C2—C1114.51 (18)C12—C11—C16122.3 (2)
N1—C2—C3124.7 (2)C16—C11—O2119.6 (2)
C3—C2—C1120.73 (19)C11—C12—H12119.8
C2—C3—H3120.9C11—C12—C13120.4 (2)
C4—C3—C2118.1 (2)C13—C12—H12119.8
C4—C3—H3120.9C12—C13—C17121.1 (2)
C3—C4—H4120.1C14—C13—C12116.6 (2)
C3—C4—C5119.8 (2)C14—C13—C17122.3 (2)
C5—C4—H4120.1C13—C14—Cl1118.67 (17)
C4—C5—C6123.2 (2)C15—C14—Cl1118.13 (17)
C4—C5—C10117.5 (2)C15—C14—C13123.2 (2)
C6—C5—C10119.4 (2)C14—C15—H15120.4
C5—C6—H6120.0C14—C15—C16119.2 (2)
C7—C6—C5119.9 (2)C16—C15—H15120.4
C7—C6—H6120.0C11—C16—C15118.3 (2)
C6—C7—H7119.6C11—C16—H16120.9
C6—C7—C8120.9 (2)C15—C16—H16120.9
C8—C7—H7119.6C13—C17—H17A109.5
C7—C8—H8119.8C13—C17—H17B109.5
C9—C8—C7120.5 (2)C13—C17—H17C109.5
C9—C8—H8119.8H17A—C17—H17B109.5
C8—C9—H9119.8H17A—C17—H17C109.5
C8—C9—C10120.3 (2)H17B—C17—H17C109.5
Cl1—C14—C15—C16−179.57 (17)C6—C5—C10—C9−2.0 (3)
O1—C1—C2—N1−13.1 (3)C6—C7—C8—C9−0.8 (4)
O1—C1—C2—C3168.7 (2)C7—C8—C9—C10−1.7 (4)
O2—C1—C2—N1166.49 (19)C8—C9—C10—N1−175.7 (2)
O2—C1—C2—C3−11.7 (3)C8—C9—C10—C53.1 (3)
O2—C11—C12—C13−177.10 (18)C10—N1—C2—C1−175.21 (17)
O2—C11—C16—C15176.69 (19)C10—N1—C2—C32.9 (3)
N1—C2—C3—C4−2.7 (3)C10—C5—C6—C7−0.4 (3)
C1—O2—C11—C12−102.0 (2)C11—O2—C1—O10.7 (3)
C1—O2—C11—C1681.7 (3)C11—O2—C1—C2−178.92 (17)
C1—C2—C3—C4175.29 (19)C11—C12—C13—C140.3 (3)
C2—N1—C10—C5−0.1 (3)C11—C12—C13—C17−179.1 (2)
C2—N1—C10—C9178.66 (19)C12—C11—C16—C150.6 (3)
C2—C3—C4—C5−0.4 (3)C12—C13—C14—Cl1179.22 (16)
C3—C4—C5—C6−176.53 (19)C12—C13—C14—C150.6 (3)
C3—C4—C5—C102.9 (3)C13—C14—C15—C16−0.9 (3)
C4—C5—C6—C7179.0 (2)C14—C15—C16—C110.3 (3)
C4—C5—C10—N1−2.8 (3)C16—C11—C12—C13−0.9 (3)
C4—C5—C10—C9178.5 (2)C17—C13—C14—Cl1−1.4 (3)
C5—C6—C7—C81.9 (4)C17—C13—C14—C15180.0 (2)
C6—C5—C10—N1176.7 (2)
D—H···AD—HH···AD···AD—H···A
C8—H8···O1i0.932.573.317 (3)138
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C8—H8⋯O1i 0.932.573.317 (3)138

Symmetry code: (i) .

  7 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.  Use of intensity quotients and differences in absolute structure refinement.

Authors:  Simon Parsons; Howard D Flack; Trixie Wagner
Journal:  Acta Crystallogr B Struct Sci Cryst Eng Mater       Date:  2013-05-17

7.  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
  7 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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