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In the title mol­ecule, C13H11NO2, one of the acetyl groups is coplanar with the quinoline ring system, whereas the other is slightly twisted from it. Inter­molecular C—H...O hydrogen bonding between methyl H atoms and both of the acetyl O atoms links the mol­ecules into a ribbon. The crystal packing is further stabilized by π–π stacking inter­actions between the pyridine rings of inversion-related mol­ecules, with the ring centroids separated by 3.5246 (9) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034769/ci2417sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034769/ci2417Isup2.hkl
Contains datablock I

CCDC reference: 657808

Key indicators

  • Single-crystal X-ray study
  • T = 203 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.049
  • wR factor = 0.114
  • Data-to-parameter ratio = 24.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 31 Perc.
Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.752
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Quinolines have been interesting to researchers for many years because a large number of natural products contain these heterocycles. They are found in numerous commercial products, including pharmaceuticals, fragrances and dyes. Quinoline alkaloids such as quinine, chloroquin, mefloquine and amodiaquine are used as efficient drugs for the treatment of malaria. Several quinoline derivatives have been evaluated in vitro against several parasites and HTLV-1 transformed cells. Prompted by the varied biological activities, the crystal structure of the title compound is reported (Fig. 1).

One acetyl group is coplanar with the quinoline ring system, with a N—C1—C10—O1 torsion angle of -178.24 (14) Å, while the second is slightly twisted out of the plane, with a C2—C3—C12—C13 torsion angle of -20.9 (2)°.

Intermolecular C—H···O hydrogen bonding interactions involving the H13A and H13B methyl hydrogen atoms and acetyl oxygen atoms O1 and O2 link the molecules into a ribbon (Fig. 2). In addition, the crystal structure is stabilized by π-π stacking interactions between the pyridine rings of the inversion-related molecules at (x, y, z) and (-x, -y, -z), with the ring centroids separated by 3.5246 (9) Å.

Related literature top

For related structures, see: Lynch & McClenaghan (2001); Firley et al. (2005); Yathirajan et al. (2007). For related literature, see: Robert & Meunier (1998); Padwa et al. (1999); Franck et al. (2004).

Experimental top

The title compound was obtained as a gift sample from Sequent Scientific Ltd, Mangalore, India. The sample was crystallized from methanol (m.p. 341–343 K).

Refinement top

The H atoms were included in the riding model approximation with C—H = 0.94 or 0.97 Å, and with Uiso(H) = 1.18–1.49Ueq(C). Owing to the poor diffraction quality of the crystal, the ratio of observed to unique reflections is low (31%).

Structure description top

Quinolines have been interesting to researchers for many years because a large number of natural products contain these heterocycles. They are found in numerous commercial products, including pharmaceuticals, fragrances and dyes. Quinoline alkaloids such as quinine, chloroquin, mefloquine and amodiaquine are used as efficient drugs for the treatment of malaria. Several quinoline derivatives have been evaluated in vitro against several parasites and HTLV-1 transformed cells. Prompted by the varied biological activities, the crystal structure of the title compound is reported (Fig. 1).

One acetyl group is coplanar with the quinoline ring system, with a N—C1—C10—O1 torsion angle of -178.24 (14) Å, while the second is slightly twisted out of the plane, with a C2—C3—C12—C13 torsion angle of -20.9 (2)°.

Intermolecular C—H···O hydrogen bonding interactions involving the H13A and H13B methyl hydrogen atoms and acetyl oxygen atoms O1 and O2 link the molecules into a ribbon (Fig. 2). In addition, the crystal structure is stabilized by π-π stacking interactions between the pyridine rings of the inversion-related molecules at (x, y, z) and (-x, -y, -z), with the ring centroids separated by 3.5246 (9) Å.

For related structures, see: Lynch & McClenaghan (2001); Firley et al. (2005); Yathirajan et al. (2007). For related literature, see: Robert & Meunier (1998); Padwa et al. (1999); Franck et al. (2004).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing atom labelling and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Part of the crystal structure of the title compound, showing the formation of C—H···O hydrogen-bonded (dashed lines) ribbons.
2,4-Diacetylquinoline top
Crystal data top
C13H11NO2F(000) = 448
Mr = 213.23Dx = 1.337 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1840 reflections
a = 7.5285 (6) Åθ = 4.6–32.5°
b = 15.0366 (12) ŵ = 0.09 mm1
c = 9.7202 (7) ÅT = 203 K
β = 105.704 (9)°Prism, pale yellow
V = 1059.28 (14) Å30.57 × 0.43 × 0.41 mm
Z = 4
Data collection top
Oxford Diffraction Gemini R
diffractometer
1078 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.058
Graphite monochromatorθmax = 32.6°, θmin = 4.6°
Detector resolution: 10.5081 pixels mm-1h = 1111
φ and ω scansk = 2219
9975 measured reflectionsl = 1414
3533 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 0.75 w = 1/[σ2(Fo2) + (0.0508P)2]
where P = (Fo2 + 2Fc2)/3
3533 reflections(Δ/σ)max = 0.001
147 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C13H11NO2V = 1059.28 (14) Å3
Mr = 213.23Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.5285 (6) ŵ = 0.09 mm1
b = 15.0366 (12) ÅT = 203 K
c = 9.7202 (7) Å0.57 × 0.43 × 0.41 mm
β = 105.704 (9)°
Data collection top
Oxford Diffraction Gemini R
diffractometer
1078 reflections with I > 2σ(I)
9975 measured reflectionsRint = 0.058
3533 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.114H-atom parameters constrained
S = 0.75Δρmax = 0.29 e Å3
3533 reflectionsΔρmin = 0.20 e Å3
147 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.19345 (15)0.03032 (8)0.46646 (11)0.0490 (3)
O20.25235 (18)0.21491 (9)0.09646 (12)0.0755 (5)
N0.09472 (16)0.07751 (9)0.17029 (12)0.0350 (3)
C10.0180 (2)0.00917 (10)0.24815 (15)0.0327 (4)
C20.05337 (19)0.07988 (11)0.20552 (15)0.0337 (4)
H20.00490.12600.26640.040*
C30.17264 (19)0.09967 (10)0.07536 (15)0.0322 (4)
C40.26019 (19)0.02745 (11)0.01274 (15)0.0313 (4)
C50.3888 (2)0.03630 (11)0.14916 (16)0.0384 (4)
H50.42450.09340.18580.046*
C60.4609 (2)0.03655 (12)0.22760 (17)0.0432 (4)
H60.54480.02900.31800.052*
C70.4124 (2)0.12220 (12)0.17607 (17)0.0444 (5)
H70.46130.17180.23240.053*
C80.2942 (2)0.13380 (11)0.04399 (17)0.0408 (4)
H80.26440.19160.00850.049*
C90.21614 (19)0.06001 (10)0.03993 (15)0.0327 (4)
C100.1207 (2)0.02998 (11)0.38780 (16)0.0375 (4)
C110.1623 (2)0.12551 (11)0.42487 (18)0.0516 (5)
H11A0.26810.12960.50790.077*
H11B0.18960.15570.34480.077*
H11C0.05640.15320.44600.077*
C120.1988 (2)0.19507 (11)0.02893 (17)0.0424 (4)
C130.1504 (2)0.26635 (12)0.13877 (18)0.0595 (5)
H13A0.18140.32380.09330.089*
H13B0.01920.26420.18560.089*
H13C0.21900.25760.20900.089*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0586 (8)0.0419 (8)0.0376 (7)0.0030 (6)0.0023 (6)0.0038 (6)
O20.1174 (11)0.0434 (9)0.0470 (8)0.0042 (8)0.0099 (7)0.0099 (7)
N0.0388 (7)0.0316 (8)0.0335 (7)0.0013 (6)0.0077 (6)0.0007 (6)
C10.0387 (9)0.0292 (9)0.0292 (9)0.0001 (7)0.0075 (7)0.0021 (7)
C20.0374 (9)0.0323 (9)0.0308 (9)0.0025 (7)0.0084 (7)0.0042 (7)
C30.0362 (9)0.0290 (9)0.0308 (9)0.0004 (7)0.0081 (7)0.0002 (8)
C40.0308 (8)0.0328 (10)0.0298 (8)0.0004 (7)0.0074 (7)0.0007 (7)
C50.0380 (9)0.0378 (11)0.0364 (9)0.0029 (8)0.0048 (7)0.0012 (8)
C60.0391 (9)0.0534 (13)0.0324 (9)0.0031 (9)0.0015 (7)0.0007 (9)
C70.0452 (10)0.0426 (12)0.0414 (10)0.0091 (8)0.0048 (8)0.0102 (9)
C80.0447 (10)0.0316 (10)0.0443 (10)0.0047 (8)0.0087 (8)0.0061 (8)
C90.0329 (8)0.0339 (10)0.0303 (8)0.0012 (7)0.0071 (7)0.0024 (8)
C100.0420 (9)0.0369 (10)0.0315 (9)0.0013 (8)0.0062 (7)0.0015 (8)
C110.0627 (11)0.0378 (11)0.0434 (10)0.0064 (9)0.0041 (9)0.0031 (9)
C120.0435 (10)0.0356 (11)0.0415 (10)0.0010 (8)0.0002 (8)0.0023 (9)
C130.0752 (13)0.0351 (11)0.0554 (11)0.0019 (10)0.0045 (10)0.0005 (9)
Geometric parameters (Å, º) top
O1—C101.2164 (17)C6—C71.394 (2)
O2—C121.2128 (17)C6—H60.94
N—C11.3137 (18)C7—C81.361 (2)
N—C91.3723 (17)C7—H70.94
C1—C21.406 (2)C8—C91.408 (2)
C1—C101.505 (2)C8—H80.94
C2—C31.3713 (19)C10—C111.493 (2)
C2—H20.94C11—H11A0.97
C3—C41.429 (2)C11—H11B0.97
C3—C121.501 (2)C11—H11C0.97
C4—C91.418 (2)C12—C131.487 (2)
C4—C51.4206 (19)C13—H13A0.97
C5—C61.361 (2)C13—H13B0.97
C5—H50.94C13—H13C0.97
C1—N—C9117.46 (13)C7—C8—H8119.7
N—C1—C2123.82 (13)C9—C8—H8119.7
N—C1—C10116.53 (14)N—C9—C8116.95 (14)
C2—C1—C10119.60 (13)N—C9—C4122.92 (13)
C3—C2—C1120.21 (14)C8—C9—C4120.10 (13)
C3—C2—H2119.9O1—C10—C11122.41 (14)
C1—C2—H2119.9O1—C10—C1119.76 (15)
C2—C3—C4117.95 (14)C11—C10—C1117.82 (14)
C2—C3—C12118.99 (13)C10—C11—H11A109.5
C4—C3—C12122.99 (13)C10—C11—H11B109.5
C9—C4—C5117.24 (14)H11A—C11—H11B109.5
C9—C4—C3117.63 (13)C10—C11—H11C109.5
C5—C4—C3125.13 (15)H11A—C11—H11C109.5
C6—C5—C4121.02 (16)H11B—C11—H11C109.5
C6—C5—H5119.5O2—C12—C13119.64 (16)
C4—C5—H5119.5O2—C12—C3121.21 (15)
C5—C6—C7121.08 (15)C13—C12—C3119.10 (13)
C5—C6—H6119.5C12—C13—H13A109.5
C7—C6—H6119.5C12—C13—H13B109.5
C8—C7—C6119.87 (16)H13A—C13—H13B109.5
C8—C7—H7120.1C12—C13—H13C109.5
C6—C7—H7120.1H13A—C13—H13C109.5
C7—C8—C9120.63 (16)H13B—C13—H13C109.5
C9—N—C1—C20.0 (2)C1—N—C9—C40.2 (2)
C9—N—C1—C10177.46 (12)C7—C8—C9—N178.39 (14)
N—C1—C2—C30.6 (2)C7—C8—C9—C40.0 (2)
C10—C1—C2—C3176.78 (13)C5—C4—C9—N179.72 (12)
C1—C2—C3—C40.9 (2)C3—C4—C9—N0.1 (2)
C1—C2—C3—C12176.29 (14)C5—C4—C9—C82.0 (2)
C2—C3—C4—C90.7 (2)C3—C4—C9—C8178.20 (13)
C12—C3—C4—C9176.44 (13)N—C1—C10—O1178.24 (14)
C2—C3—C4—C5179.12 (13)C2—C1—C10—O14.2 (2)
C12—C3—C4—C53.8 (2)N—C1—C10—C111.2 (2)
C9—C4—C5—C62.3 (2)C2—C1—C10—C11176.43 (15)
C3—C4—C5—C6177.91 (15)C2—C3—C12—O2156.46 (15)
C4—C5—C6—C70.6 (2)C4—C3—C12—O220.6 (2)
C5—C6—C7—C81.5 (3)C2—C3—C12—C1320.9 (2)
C6—C7—C8—C91.7 (2)C4—C3—C12—C13162.01 (14)
C1—N—C9—C8178.57 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13A···O1i0.972.573.531 (2)173
C13—H13B···O2ii0.972.513.392 (2)151
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x1/2, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC13H11NO2
Mr213.23
Crystal system, space groupMonoclinic, P21/n
Temperature (K)203
a, b, c (Å)7.5285 (6), 15.0366 (12), 9.7202 (7)
β (°) 105.704 (9)
V3)1059.28 (14)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.57 × 0.43 × 0.41
Data collection
DiffractometerOxford Diffraction Gemini R
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
9975, 3533, 1078
Rint0.058
(sin θ/λ)max1)0.758
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.114, 0.75
No. of reflections3533
No. of parameters147
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.20

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis PRO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13A···O1i0.972.573.531 (2)173
C13—H13B···O2ii0.972.513.392 (2)151
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x1/2, y+1/2, z1/2.
 

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