2,6 Di­methyl­quinolin 4(1H) one

organic papers

o1768

Structure Reports Online

ISSN 1600-5368

2,6-Dimethylquinolin-4(1

H

)-one

Rajnikant,a_{* Dinesh,}a

M. B. Deshmukhb_and

Kamnia

a_{Condensed Matter Physics Group, Department} of Physics, University of Jammu, Jammu Tawi 180 006, India, andb_{Department of Chemistry,} Sivaji University Kolhapur, Kolhapur 416 004, Maharastra, India

Correspondence e-mail: [email protected]

Key indicators

Single-crystal X-ray study T= 293 K

Mean(C±C) = 0.003 AÊ Rfactor = 0.043 wRfactor = 0.134

Data-to-parameter ratio = 13.5

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

#2003 International Union of Crystallography Printed in Great Britain ± all rights reserved

The structure of 2,6-dimethylquinolin-4(1H)-one, C11H11NO,

has been determined as part of our study on the synthesis and crystallography of quinoline and quinazoline derivatives. It crystallizes in the monoclinic space groupP21/c. The molecule

is planar, with the dihedral angle between the planes of the two rings being 2 (1)_.

Comment

Compounds containing a quinoline moiety are of considerable interest due to their biological properties (Zacharias & Glusker, 1988; Hua & Chen, 1997; Newellet al., 1998); these include high antibacterial, antiarrhythmic and anti-hypertensive activities (Yates, 1984; Jones, 1977). The crystal structures of related compounds have been reported previously (Rajnikantet al., 2000, 2001; Rajnikant, Gupta, Suri & Lal, 2002; Rajnikant, Gupta, Deshmukh & Varghese, 2002).

Bond distances and angles in the quinoline ring system of the title compound, (I), are normal (Sudha, Subramanian, Sivaraman, Ramakrishnan et al., 1995; Sudha, Subramanian, Sivaraman, Sriraghavan & Steiner, 1995; Sudha et al., 1997; Rajnikant, Gupta, Deshmukh & Varghese, 2002). The double-bond character of C4 O1 is con®rmed by its length [1.262 (2) AÊ]. The angle between the planes of the two rings is 2 (1)_{, con®rming that the molecule is planar. There is a strong}

intermolecular hydrogen bond N1ÐH1 O1i_{, with H A=}

1.89 AÊ,DÐH A= 174_{and D A= 2.743 (1) AÊ [symmetry}

code: (i)x,1

2ÿy,z+12].

Received 11 September 2003 Accepted 14 October 2003 Online 23 October 2003

Figure 1

Experimental

A mixture ofp-toluidine (0.01 mol) and ethyl acetoacetate (0.01 mol) in ethanol (20 ml) was stirred for 2±3 h and allowed to stand for 36 h. The mixture was then concentrated, giving a viscous oily liquid which was vacuum distilled to afford 2-(p-methylbenzylidene)ethyl butyrate in 60% yield. This latter compound (0.1 mol) and H2SO4(75 ml) were

heated on an oil bath at 323 K for 0.5 h, at 373 K for a further 3 h, cooled and poured on to crushed ice, giving the title compound (yield 50%), which was then recrystallized from ethanol.

Crystal data C11H11NO

Mr= 173.21

Monoclinic,P21=c

a= 9.068 (7) AÊ

b= 8.352 (3) AÊ

c= 12.253 (5) AÊ

= 94.15 (4)

V= 925.6 (9) AÊ3

Z= 4

Dx= 1.243 Mg mÿ3

Mo Kradiation Cell parameters from 25

re¯ections

= 6.2±11.5 = 0.08 mmÿ1

T= 293 (2) K Plate, yellow 0.40.30.1 mm Data collection

Enraf±Nonius CAD-4 diffractometer

!/2scans

Absorption correction: none 1737 measured re¯ections 1629 independent re¯ections 1306 re¯ections withI> 2(I)

Rint= 0.009

max= 25.0

h= 0!10

k= 0!9

l=ÿ14!14 2 standard re¯ections

frequency: 60 min intensity decay:<2%

Re®nement Re®nement onF2

R[F2_{> 2(F}2_{)] = 0.043}

wR(F2_{) = 0.135}

S= 1.09 1629 re¯ections 121 parameters

H-atom parameters constrained

w= 1/[2_(F

o2) + (0.0684P)2

+ 0.2584P]

whereP= (Fo2+ 2Fc2)/3

(/)max< 0.001 max= 0.24 e AÊÿ3 min=ÿ0.15 e AÊÿ3

Extinction correction:SHELXL97 Extinction coef®cient: 0.020 (5)

Table 1

Selected geometric parameters (AÊ,_).

O1ÐC4 1.2618 (19) N1ÐC2 1.351 (2) N1ÐC9 1.379 (2) C2ÐC3 1.366 (2) C2ÐC12 1.502 (3) C3ÐC4 1.418 (2) C4ÐC10 1.461 (2)

C5ÐC6 1.371 (2) C5ÐC10 1.406 (2) C6ÐC7 1.405 (3) C6ÐC11 1.505 (3) C7ÐC8 1.366 (3) C8ÐC9 1.406 (2) C9ÐC10 1.400 (2)

C2ÐN1ÐC9 121.81 (14) N1ÐC2ÐC3 120.48 (15) N1ÐC2ÐC12 116.38 (16) C3ÐC2ÐC12 123.13 (17) C2ÐC3ÐC4 122.37 (16) O1ÐC4ÐC3 122.82 (15) O1ÐC4ÐC10 121.44 (15) C3ÐC4ÐC10 115.74 (15) C6ÐC5ÐC10 122.28 (16) C5ÐC6ÐC7 117.55 (16)

C5ÐC6ÐC11 121.09 (17) C7ÐC6ÐC11 121.36 (17) C8ÐC7ÐC6 122.37 (16) C7ÐC8ÐC9 119.38 (16) N1ÐC9ÐC10 119.86 (14) N1ÐC9ÐC8 120.34 (15) C10ÐC9ÐC8 119.80 (15) C9ÐC10ÐC5 118.58 (15) C9ÐC10ÐC4 119.69 (15) C5ÐC10ÐC4 121.73 (15)

All H atoms were included in the ®nal cycles of re®nement; they were constrained to ride on their parent atoms, with Uiso(H) =

xUeq(parent), where x= 1.5 for methyl and 1.2 for all others. The

Data collection: CAD-4 Software (Enraf±Nonius, 1989); cell re®nement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure:SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); soft-ware used to prepare material for publication:PARST95 (Nardelli, 1995).

Rajnikant is grateful to the University Grants Commission, Government of India, for funding under DRS Project No. F.530/3/DRS/2001 (SAP±I).

References

Enraf±Nonius (1989).CAD-4Software. Version 5.0. Enraf±Nonius, Delft, The Netherlands.

Farrugia, L. J. (1997).J. Appl. Cryst.30, 565.

Hua, D. H., Chen, Y. &Sin, H. S. (1997).J. Org. Chem.62, 6888±6896. Jones, G. (1977).Chemistry of Heterocyclic Compounds: I.Quinolines, edited

by G. Jones, p. 93. Chichester: Wiley. Nardelli, M. (1995).J. Appl. Cryst.28, 659.

Newell, S. W., Perchellet, E. M. & Ladesich, J. B. (1998).Int. J. Oncol.12, 433± 437.

Rajnikant, Gupta, V. K., Deshmukh, M. B., Varghese, B. & Dinesh (2001).

Cryst. Res. Technol.36, 1451±1456.

Rajnikant, Gupta, V. K., Deshmukh, M. B., Varghese, B. & Dinesh (2002).

Crystallogr. Rep.47, 494±496.

Rajnikant, Gupta, V. K. & Singh, A. (2000).Crystallogr. Rep.45, 611±614. Rajnikant, Gupta, V. K., Suri, O. P. & Lal, M. (2002).Indian J. Pure Appl.

Phys.40, 59±61.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of GoÈttingen, Germany.

Sudha, L., Subramanian, K., Sivaraman, J., Ramakrishnan, V. T. R., Steiner, Th. & Koellner, G. (1995).Acta Cryst.C51, 1026±1028.

Sudha, L., Subramanian, K., Sivaraman, J., Sriraghavan, K. & Steiner, Th. (1995).Acta Cryst.C51, 1689±1691.

Sudha, L., Subramanian, K., Steiner, Th., Koellner, G., Ramakrishnan, V. T. R. & Sriraghavan, K. (1997).Acta Cryst.C53, 606±607.

Yates, F. S. (1984).Comprehensive Heterocyclic Chemistry, edited by A. R.

Figure 2

supporting information

sup-1 Acta Cryst. (2003). E59, o1768–o1769

supporting information

Acta Cryst. (2003). E59, o1768–o1769 [https://doi.org/10.1107/S1600536803023249]

2,6-Dimethylquinolin-4(1

H

)-one

Rajnikant, Dinesh, M. B. Deshmukh and Kamni

2,6-dimethylquinolin-4(1H)-one

Crystal data

C11H11NO Mr = 173.21

Monoclinic, P21/c

Hall symbol: -P2ybc

a = 9.068 (7) Å

b = 8.352 (3) Å

c = 12.253 (5) Å

β = 94.15 (4)°

V = 925.6 (9) Å3 Z = 4

F(000) = 368

Dx = 1.243 Mg m−3

Melting point: 533 K

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 25 reflections

θ = 6.2–11.5°

µ = 0.08 mm−1 T = 293 K Plate-like, yellow 0.4 × 0.3 × 0.1 mm

Data collection

Enraf-Nonius CAD-4 diffractometer

Radiation source: fine-focus sealed tube, Laboratory X-ray Generator

Graphite monochromator

ω/2θ scans

1737 measured reflections 1629 independent reflections

1306 reflections with I > 2σ(I)

Rint = 0.009

θmax = 25.0°, θmin = 2.3° h = 0→10

k = 0→9

l = −14→14

2 standard reflections every 60 min intensity decay: <2%

Refinement

Refinement on F2

Least-squares matrix: full

R[F2 _{> 2σ(F}2_{)] = 0.043} wR(F2_{) = 0.135} S = 1.09 1629 reflections 121 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained

w = 1/[σ2_(F

o2) + (0.0684P)2 + 0.2584P]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max < 0.001

Δρmax = 0.24 e Å−3

Δρmin = −0.15 e Å−3

Extinction correction: SHELXL97, fc*_{=kfc[1+0.001xfc}2_λ3_/sin(2θ)]-1/4

Special details

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 f}2_,

conventional r-factors r are based on f, with f set to zero for negative f2_{. the threshold expression of f}2 _{> σ(f}2_{) 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₎

x y z Uiso*/Ueq

O1 0.71725 (14) 0.42824 (15) −0.03411 (9) 0.0533 (4) N1 0.71513 (14) 0.20258 (17) 0.26042 (11) 0.0432 (4) H1 0.7136 0.1556 0.3228 0.052* C2 0.59707 (18) 0.2905 (2) 0.22294 (14) 0.0441 (4) C3 0.59554 (18) 0.3650 (2) 0.12367 (14) 0.0457 (4) H3 0.5118 0.4223 0.0988 0.055* C4 0.71705 (18) 0.3583 (2) 0.05716 (12) 0.0406 (4) C5 0.97234 (18) 0.2492 (2) 0.04407 (13) 0.0439 (4) H5 0.9769 0.3018 −0.0225 0.053* C6 1.09121 (19) 0.1596 (2) 0.08344 (15) 0.0473 (5) C7 1.08045 (19) 0.0802 (2) 0.18367 (15) 0.0520 (5) H7 1.1597 0.0183 0.2115 0.062* C8 0.95775 (19) 0.0909 (2) 0.24175 (14) 0.0481 (5) H8 0.9534 0.0356 0.3073 0.058* C9 0.83806 (17) 0.18606 (19) 0.20141 (12) 0.0390 (4) C10 0.84381 (17) 0.26447 (19) 0.10086 (12) 0.0382 (4) C11 1.2274 (2) 0.1455 (3) 0.02081 (18) 0.0648 (6) H11a 1.1990 0.1223 −0.0545 0.097* H11b 1.2888 0.0607 0.0513 0.097* H11c 1.2812 0.2445 0.0257 0.097* C12 0.4717 (2) 0.3012 (3) 0.29634 (18) 0.0631 (6) H12a 0.4408 0.1953 0.3149 0.095* H12b 0.3904 0.3572 0.2591 0.095* H12c 0.5039 0.3580 0.3619 0.095*

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

supporting information

sup-3 Acta Cryst. (2003). E59, o1768–o1769

C8 0.0504 (10) 0.0504 (10) 0.0433 (9) 0.0080 (8) 0.0006 (8) 0.0050 (8) C9 0.0395 (9) 0.0395 (9) 0.0380 (8) 0.0002 (7) 0.0028 (7) −0.0040 (7) C10 0.0403 (9) 0.0391 (9) 0.0351 (8) 0.0002 (7) 0.0009 (6) −0.0053 (6) C11 0.0475 (11) 0.0724 (14) 0.0762 (14) 0.0037 (10) 0.0158 (10) −0.0114 (11) C12 0.0512 (11) 0.0705 (13) 0.0701 (13) 0.0058 (10) 0.0210 (10) 0.0061 (10)

Geometric parameters (Å, º)

O1—C4 1.2618 (19) C6—C11 1.505 (3) N1—C2 1.351 (2) C7—C8 1.366 (3) N1—C9 1.379 (2) C7—H7 0.9300 N1—H1 0.8600 C8—C9 1.406 (2) C2—C3 1.366 (2) C8—H8 0.9300 C2—C12 1.502 (3) C9—C10 1.400 (2) C3—C4 1.418 (2) C11—H11a 0.9600 C3—H3 0.9300 C11—H11b 0.9600 C4—C10 1.461 (2) C11—H11c 0.9600 C5—C6 1.371 (2) C12—H12a 0.9600 C5—C10 1.406 (2) C12—H12b 0.9600 C5—H5 0.9300 C12—H12c 0.9600 C6—C7 1.405 (3)

C2—N1—C9 121.81 (14) C7—C8—C9 119.38 (16) C2—N1—H1 119.1 C7—C8—H8 120.3 C9—N1—H1 119.1 C9—C8—H8 120.3 N1—C2—C3 120.48 (15) N1—C9—C10 119.86 (14) N1—C2—C12 116.38 (16) N1—C9—C8 120.34 (15) C3—C2—C12 123.13 (17) C10—C9—C8 119.80 (15) C2—C3—C4 122.37 (16) C9—C10—C5 118.58 (15) C2—C3—H3 118.8 C9—C10—C4 119.69 (15) C4—C3—H3 118.8 C5—C10—C4 121.73 (15) O1—C4—C3 122.82 (15) C6—C11—H11a 109.5 O1—C4—C10 121.44 (15) C6—C11—H11b 109.5 C3—C4—C10 115.74 (15) H11a—C11—H11b 109.5 C6—C5—C10 122.28 (16) C6—C11—H11c 109.5 C6—C5—H5 118.9 H11a—C11—H11c 109.5 C10—C5—H5 118.9 H11b—C11—H11c 109.5 C5—C6—C7 117.55 (16) C2—C12—H12a 109.5 C5—C6—C11 121.09 (17) C2—C12—H12b 109.5 C7—C6—C11 121.36 (17) H12a—C12—H12b 109.5 C8—C7—C6 122.37 (16) C2—C12—H12c 109.5 C8—C7—H7 118.8 H12a—C12—H12c 109.5 C6—C7—H7 118.8 H12b—C12—H12c 109.5