Literature DB >> 21579109

1-[(2-Chloro-8-methyl-quinolin-3-yl)-meth-yl]pyridin-2(1H)-one.

Atul Kumar Kushwaha, S Mohana Roopan, F Nawaz Khan, Venkatesha R Hathwar, Mehmet Akkurt.   

Abstract

In the title compound, C(16)H(13)ClN(2)O, the quinoline ring system is approximately planar [maximum deviation 0.021 (2) Å] and forms a dihedral angle of 85.93 (6)° with the pyridone ring. Inter-molecular C-H⋯O hydrogen bonding, together with weak C-H⋯π and π-π inter-actions [centroid-to-centroid distances 3.5533 (9) and 3.7793 (9) Å], characterize the crystal structure.

Entities:  

Year:  2010        PMID： 21579109      PMCID： PMC2979145          DOI： 10.1107/S1600536810012730

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


Related literature

For 2-pyridone analogues, see: Arman et al. (2009 ▶); Clegg & Nichol (2004 ▶); Nichol & Clegg (2005 ▶). For the synthesis of 2-pyridone derivatives, see: Banerjee & Sereda (2009 ▶); Roopan & Khan (2009 ▶); Roopan et al. (2010 ▶); Dandepally & Williams (2009 ▶).

Experimental

Crystal data

C16H13ClN2O M = 284.73 Monoclinic, a = 10.1513 (2) Å b = 9.3917 (2) Å c = 14.1430 (2) Å β = 90.948 (2)° V = 1348.17 (4) Å3 Z = 4 Mo Kα radiation μ = 0.28 mm−1 T = 295 K 0.26 × 0.24 × 0.20 mm

Data collection

Oxford Xcalibur Eos (Nova) CCD detector diffractometer Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.931, T max = 0.946 17649 measured reflections 2511 independent reflections 2088 reflections with I > 2σ(I) R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.034 wR(F 2) = 0.100 S = 1.10 2511 reflections 182 parameters H-atom parameters constrained Δρmax = 0.16 e Å−3 Δρmin = −0.33 e Å−3 Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: 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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810012730/im2191sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012730/im2191Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H13ClN2OF(000) = 592
Mr = 284.73Dx = 1.403 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1116 reflections
a = 10.1513 (2) Åθ = 2.0–21.0°
b = 9.3917 (2) ŵ = 0.28 mm−1
c = 14.1430 (2) ÅT = 295 K
β = 90.948 (2)°Block, colourless
V = 1348.17 (4) Å30.26 × 0.24 × 0.20 mm
Z = 4
Oxford Xcalibur Eos (Nova) CCD detector diffractometer2511 independent reflections
Radiation source: Enhance (Mo) X-ray Source2088 reflections with I > 2σ(I)
graphiteRint = 0.033
ω scansθmax = 25.5°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)h = −12→12
Tmin = 0.931, Tmax = 0.946k = −11→11
17649 measured reflectionsl = −17→17
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.0626P)2 + 0.062P] where P = (Fo2 + 2Fc2)/3
2511 reflections(Δ/σ)max < 0.001
182 parametersΔρmax = 0.16 e Å−3
0 restraintsΔρmin = −0.33 e Å−3
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.
xyzUiso*/Ueq
Cl10.17214 (4)0.42990 (4)0.02479 (2)0.0424 (1)
O10.08041 (10)0.28868 (13)0.35614 (8)0.0481 (4)
N10.32267 (11)0.61310 (13)0.11096 (8)0.0315 (4)
N2−0.05971 (11)0.45168 (13)0.28993 (8)0.0331 (4)
C10.21630 (13)0.53822 (15)0.12066 (9)0.0292 (4)
C20.13534 (13)0.53361 (14)0.20141 (9)0.0281 (4)
C30.17568 (13)0.61625 (16)0.27547 (10)0.0304 (4)
C40.33798 (15)0.78326 (17)0.34745 (11)0.0407 (5)
C50.45224 (16)0.8575 (2)0.33878 (12)0.0498 (6)
C60.52323 (16)0.8519 (2)0.25493 (12)0.0499 (6)
C70.48186 (15)0.77503 (17)0.17819 (12)0.0405 (5)
C80.36339 (13)0.69521 (15)0.18602 (10)0.0307 (4)
C90.29139 (13)0.69933 (15)0.27116 (10)0.0305 (4)
C100.01318 (15)0.44264 (17)0.20158 (10)0.0365 (5)
C11−0.16498 (15)0.54157 (17)0.29568 (12)0.0430 (5)
C12−0.23606 (17)0.54973 (19)0.37505 (14)0.0520 (6)
C13−0.20074 (17)0.4635 (2)0.45186 (13)0.0507 (6)
C14−0.09706 (16)0.37454 (18)0.44725 (11)0.0433 (5)
C15−0.01782 (14)0.36501 (16)0.36452 (10)0.0342 (5)
C160.55794 (17)0.7727 (2)0.08775 (14)0.0626 (7)
H30.126000.618000.330100.0360*
H40.290900.787800.403200.0490*
H50.483400.912600.389100.0600*
H60.601700.902600.251400.0600*
H10A−0.044300.471700.149600.0440*
H10B0.038000.344300.190900.0440*
H11−0.188000.598000.244000.0520*
H12−0.307300.611600.378700.0630*
H13−0.249500.467600.506900.0610*
H14−0.076200.317700.499200.0520*
H16A0.510200.824500.039700.0940*
H16B0.569600.675900.067600.0940*
H16C0.642500.816100.098200.0940*
U11U22U33U12U13U23
Cl10.0429 (2)0.0526 (3)0.0316 (2)−0.0044 (2)0.0012 (2)−0.0104 (2)
O10.0446 (7)0.0512 (7)0.0485 (7)0.0098 (6)0.0006 (5)0.0002 (5)
N10.0289 (6)0.0345 (7)0.0311 (6)0.0019 (5)0.0023 (5)0.0027 (5)
N20.0289 (6)0.0350 (7)0.0354 (7)−0.0063 (5)0.0027 (5)−0.0005 (5)
C10.0295 (7)0.0312 (8)0.0269 (7)0.0038 (6)−0.0021 (5)0.0010 (6)
C20.0258 (7)0.0286 (7)0.0298 (7)0.0023 (6)0.0000 (5)0.0022 (6)
C30.0297 (7)0.0331 (8)0.0286 (7)0.0013 (6)0.0038 (5)−0.0001 (6)
C40.0464 (9)0.0410 (9)0.0347 (8)−0.0080 (7)0.0020 (7)−0.0044 (7)
C50.0568 (11)0.0489 (10)0.0433 (9)−0.0172 (9)−0.0076 (8)−0.0057 (8)
C60.0423 (9)0.0503 (10)0.0570 (10)−0.0196 (8)−0.0006 (8)0.0013 (9)
C70.0345 (8)0.0406 (9)0.0466 (9)−0.0065 (7)0.0036 (6)0.0031 (7)
C80.0293 (7)0.0288 (8)0.0341 (7)0.0018 (6)−0.0005 (6)0.0026 (6)
C90.0314 (7)0.0288 (8)0.0314 (7)−0.0001 (6)−0.0001 (6)0.0007 (6)
C100.0358 (8)0.0439 (9)0.0299 (7)−0.0073 (7)0.0017 (6)−0.0022 (6)
C110.0366 (9)0.0367 (9)0.0556 (10)−0.0018 (7)0.0006 (7)0.0073 (8)
C120.0406 (9)0.0459 (11)0.0701 (12)0.0062 (8)0.0151 (8)−0.0027 (9)
C130.0518 (10)0.0521 (11)0.0487 (10)−0.0047 (8)0.0186 (8)−0.0046 (8)
C140.0475 (9)0.0463 (10)0.0363 (8)−0.0073 (8)0.0046 (7)0.0008 (7)
C150.0351 (8)0.0324 (8)0.0352 (8)−0.0072 (7)−0.0003 (6)−0.0032 (6)
C160.0502 (11)0.0774 (14)0.0609 (12)−0.0236 (10)0.0197 (9)−0.0053 (10)
Cl1—C11.7476 (14)C11—C121.347 (3)
O1—C151.2354 (18)C12—C131.397 (3)
N1—C11.2978 (18)C13—C141.346 (2)
N1—C81.3704 (18)C14—C151.434 (2)
N2—C101.4651 (18)C3—H30.9300
N2—C111.3653 (19)C4—H40.9300
N2—C151.3934 (19)C5—H50.9300
C1—C21.4187 (18)C6—H60.9300
C2—C31.3612 (19)C10—H10A0.9700
C2—C101.506 (2)C10—H10B0.9700
C3—C91.4123 (19)C11—H110.9300
C4—C51.361 (2)C12—H120.9300
C4—C91.412 (2)C13—H130.9300
C5—C61.399 (2)C14—H140.9300
C6—C71.364 (2)C16—H16A0.9600
C7—C81.423 (2)C16—H16B0.9600
C7—C161.505 (3)C16—H16C0.9600
C8—C91.419 (2)
Cl1···O1i3.2706 (12)C14···C14ix3.401 (2)
Cl1···H10A2.8700C15···C3iv3.441 (2)
Cl1···H10Aii2.9200C15···C2iv3.456 (2)
Cl1···H16Biii3.1100C15···C33.331 (2)
Cl1···H10B2.8500C1···H6vi2.8600
O1···C23.2298 (17)C2···H6vi3.0000
O1···C2iv3.3375 (17)C3···H6vi3.0500
O1···C11iv3.286 (2)C3···H10Bvii3.0900
O1···Cl1v3.2706 (12)C8···H6vi2.9100
O1···H10B2.4300C9···H6vi3.0100
O1···H11iv2.5400C11···H33.0700
O1···H16Cvi2.8900C15···H32.8400
N1···C14vii3.448 (2)H3···N22.5100
N1···C5vi3.382 (2)H3···C113.0700
N2···C9iv3.4391 (18)H3···C152.8400
N1···H16B2.6600H3···H42.5200
N1···H5vi2.7200H3···H14ix2.5500
N1···H6vi2.8700H4···H32.5200
N1···H16A2.9400H5···N1viii2.7200
N2···H32.5100H6···H16C2.3600
C1···C14vii3.511 (2)H6···N1viii2.8700
C2···C15vii3.456 (2)H6···C1viii2.8600
C2···O13.2298 (17)H6···C2viii3.0000
C2···O1vii3.3375 (17)H6···C3viii3.0500
C3···C15vii3.441 (2)H6···C8viii2.9100
C3···C113.545 (2)H6···C9viii3.0100
C3···C153.331 (2)H10A···Cl12.8700
C4···C11vii3.599 (2)H10A···H112.3200
C5···N1viii3.382 (2)H10A···Cl1ii2.9200
C6···C8viii3.519 (2)H10B···Cl12.8500
C8···C13vii3.574 (2)H10B···O12.4300
C8···C6vi3.519 (2)H10B···C3iv3.0900
C9···C11vii3.582 (2)H11···H10A2.3200
C9···N2vii3.4391 (18)H11···O1vii2.5400
C11···C9iv3.582 (2)H14···H3ix2.5500
C11···C33.545 (2)H16A···N12.9400
C11···C4iv3.599 (2)H16B···N12.6600
C11···O1vii3.286 (2)H16B···Cl1iii3.1100
C13···C8iv3.574 (2)H16C···H62.3600
C14···N1iv3.448 (2)H16C···O1viii2.8900
C14···C1iv3.511 (2)
C1—N1—C8117.64 (12)O1—C15—C14125.40 (14)
C10—N2—C11119.57 (12)N2—C15—C14114.40 (13)
C10—N2—C15117.37 (12)C2—C3—H3119.00
C11—N2—C15123.06 (12)C9—C3—H3119.00
Cl1—C1—N1115.89 (10)C5—C4—H4120.00
Cl1—C1—C2117.53 (10)C9—C4—H4120.00
N1—C1—C2126.57 (12)C4—C5—H5120.00
C1—C2—C3115.54 (12)C6—C5—H5120.00
C1—C2—C10120.44 (12)C5—C6—H6119.00
C3—C2—C10124.02 (12)C7—C6—H6119.00
C2—C3—C9121.44 (13)N2—C10—H10A109.00
C5—C4—C9119.52 (14)N2—C10—H10B109.00
C4—C5—C6120.60 (16)C2—C10—H10A109.00
C5—C6—C7122.57 (16)C2—C10—H10B109.00
C6—C7—C8117.80 (15)H10A—C10—H10B108.00
C6—C7—C16121.89 (15)N2—C11—H11120.00
C8—C7—C16120.31 (14)C12—C11—H11119.00
N1—C8—C7118.73 (13)C11—C12—H12121.00
N1—C8—C9121.30 (12)C13—C12—H12121.00
C7—C8—C9119.96 (13)C12—C13—H13120.00
C3—C9—C4122.95 (13)C14—C13—H13120.00
C3—C9—C8117.51 (13)C13—C14—H14119.00
C4—C9—C8119.54 (13)C15—C14—H14119.00
N2—C10—C2113.33 (12)C7—C16—H16A110.00
N2—C11—C12121.03 (15)C7—C16—H16B109.00
C11—C12—C13118.75 (16)C7—C16—H16C109.00
C12—C13—C14120.86 (16)H16A—C16—H16B109.00
C13—C14—C15121.87 (15)H16A—C16—H16C109.00
O1—C15—N2120.20 (13)H16B—C16—H16C109.00
C8—N1—C1—Cl1−177.53 (10)C2—C3—C9—C80.9 (2)
C8—N1—C1—C20.9 (2)C9—C4—C5—C60.4 (3)
C1—N1—C8—C7178.16 (13)C5—C4—C9—C3178.26 (15)
C1—N1—C8—C9−0.5 (2)C5—C4—C9—C8−0.9 (2)
C11—N2—C10—C297.14 (15)C4—C5—C6—C71.0 (3)
C15—N2—C10—C2−83.63 (16)C5—C6—C7—C8−1.7 (3)
C10—N2—C11—C12178.31 (15)C5—C6—C7—C16178.65 (17)
C15—N2—C11—C12−0.9 (2)C6—C7—C8—N1−177.62 (14)
C10—N2—C15—O12.8 (2)C6—C7—C8—C91.1 (2)
C10—N2—C15—C14−177.33 (13)C16—C7—C8—N12.1 (2)
C11—N2—C15—O1−177.96 (14)C16—C7—C8—C9−179.25 (14)
C11—N2—C15—C141.9 (2)N1—C8—C9—C3−0.4 (2)
Cl1—C1—C2—C3178.03 (10)N1—C8—C9—C4178.84 (13)
Cl1—C1—C2—C10−2.45 (18)C7—C8—C9—C3−179.02 (13)
N1—C1—C2—C3−0.4 (2)C7—C8—C9—C40.2 (2)
N1—C1—C2—C10179.10 (14)N2—C11—C12—C13−0.4 (3)
C1—C2—C3—C9−0.6 (2)C11—C12—C13—C140.5 (3)
C10—C2—C3—C9179.96 (14)C12—C13—C14—C150.6 (3)
C1—C2—C10—N2−179.27 (12)C13—C14—C15—O1178.08 (16)
C3—C2—C10—N20.2 (2)C13—C14—C15—N2−1.7 (2)
C2—C3—C9—C4−178.28 (14)
D—H···AD—HH···AD···AD—H···A
C3—H3···N20.932.512.8560 (18)103
C11—H11···O1vii0.932.543.286 (2)137
C6—H6···Cg1viii0.932.613.4457 (18)150
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C1–C3/C8/C9 ring.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C11—H11⋯O1i0.932.543.286 (2)137
C6—H6⋯Cg1ii0.932.613.4457 (18)150

Symmetry codes: (i) ; (ii) .

  4 in total

1.  A short history of SHELX.

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

2.  6-Methyl-2-pyridone: an elusive structure finally solved.

Authors:  Gary S Nichol; William Clegg
Journal:  Acta Crystallogr C       Date:  2005-05-13       Impact factor: 1.172

3.  2-Pyridone: monoclinic polymorph.

Authors:  Hadi D Arman; Pavel Poplaukhin; Edward R T Tiekink
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-11-25

4.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  4 in total
  1 in total

1.  N-[2-(4-Methyl-2-quinol-yl)phen-yl]acetamide: a P1 structure with Z = 4.

Authors:  F Nawaz Khan; S Mohana Roopan; N Malathi; Venkatesha R Hathwar; Mehmet Akkurt
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-07-17
  1 in total

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