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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o112
https://doi.org/10.1107/S1600536807042948

7-Acetyl­amino-2,4-di­methyl-1,8-naphthyridine

De-Hui Wang,a Yao-Ming Yu,a Jian-Hua Chena and Wen-Fu Fub*

aCollege of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650092, People's Republic of China, and bCollege of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650092, People's Republic of China, and Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100080, People's Republic of China
*Correspondence e-mail: fuwfu@sohu.com

(Received 1 December 2006; accepted 2 September 2007; online 6 December 2007)

The air-stable title compound, C12H13N3O, which is of inter­est due to its anti­bacterial properties, is an almost planar mol­ecule in which the ten atoms forming the 1,8-naphthyridine ring have an r.m.s. deviation of 0.03 Å from the least-squares plane calculated using the ten atoms. The plane of the acetyl­amino group is slightly inclined [11.7 (2)°] to the plane of the 1,8-naphthyridine ring.

Related literature

For related literature, see: Catalano et al. (2000[Catalano, V. J., Kar, H. M. & Bennett, B. L. (2000). Inorg. Chem. 39, 121-127.]); Chen et al. (2001[Chen, Y.-L., Fang, K.-C., Sheu, J.-Y., Hsu, S.-L. & Tzeng, C.-C. (2001). J. Med. Chem. 44, 2374-2378.]); Ferrarini et al. (1997[Ferrarini, P. L., Mori, C., Badawneh, M., Manera, C., Martinelli, A., Miceli, M., Ramagnoli, F. & Saccomanni, G. (1997). J. Heterocycl. Chem. 34, 1501-1504.], 2000[Ferrarini, P. L., Mori, C., Badawneh, M., Calderone, V., Greco, R., Manera, C., Martinelli, A., Nieri, P. & Saccomanni, G. (2000). Eur. J. Chem. 35, 815-819.]); He & Lippard (2001[He, C. & Lippard, S. J. (2001). J. Am. Chem. Soc. 40, 1414-1419.]); Henry & Hammond (1977[Henry, R. A. & Hammond, P. R. (1977). J. Heterocycl. Chem. 14, 1109-1112.]); Mogilaiah et al. (2001[Mogilaiah, K., Chowdary, D. S. & Rao, R. B. (2001). Indian J. Chem. pp. 40-43.]); Nakatani et al. (2000[Nakatani, K., Sando, S. & Saito, I. (2000). J. Am. Chem. Soc. 122, 2172-2178.]); Roma et al. (2000[Roma, G., Braccio, M. D., Grossi, G., Mattioli, F. & Ghia, M. (2000). Eur. J. Med. Chem. 35, 1021-1026.]); Saito et al. (2001[Saito, I., Sando, S. & Nakatani, K. (2001). Bioorg. Med. Chem. 9, 2381-2387.]).

[Scheme 1]

Experimental

Crystal data

  • C12H13N3O

  • Mr = 215.25

  • Monoclinic, P 21 /n

  • a = 7.970 (8) Å

  • b = 7.309 (7) Å

  • c = 19.071 (18) Å

  • β = 91.883 (14)°

  • V = 1110.4 (18) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 298 (2) K

  • 0.52 × 0.36 × 0.24 mm
Data collection

  • SMART 1K CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2002[Sheldrick, G. M. (2002). SADABS. Version 2.03. University of Göttingen, Germany.]) Tmin = 0.970, Tmax = 0.980

  • 5375 measured reflections

  • 1959 independent reflections

  • 1169 reflections with I > 2σ(I)

  • Rint = 0.036
Refinement

  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.153

  • S = 1.02

  • 1959 reflections

  • 145 parameters

  • H-atom parameters constrained

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT, XPREP and XP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT, XPREP and XP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: DIAMOND (Bergerhoff, 1996[Bergerhoff, G. (1996). DIAMOND. Version 1.2. Gerhard-Domagk Str. 1, D-53121 Bonn, Germany.]) and XP (Bruker, 2000[Bruker (2000). SMART, SAINT, XPREP and XP. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2000[Sheldrick, G. M. (2000). SHELXTL. Version 6.10. Bruker AXS Inc., Madison, Wisconsin, USA.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807042948/er2027sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807042948/er2027Isup2.hkl

checkCIF report


Comment top

The 1,8-naphthyridine compounds have been the focus of studies and practical applications as antibacterial agents (Mogilaiah et al., 2001). Recent parallels in biological activity of this class of compounds have been found in the form of antibacterial (Chen et al., 2001), antiinflammatory (Roma et al., 2000), antihypertensive (Ferrarini et al., 2000), and antiplatelet activity (Ferrarini et al., 1997). In addition to medicinal applications, this class of compounds have been employed in the study of bioorganic and bioorganometallic processes (Saito et al., 2001; He et al., 2001; Nakatani et al., 2000). The structure of the C12H13N3O in (I) is shown in Fig. 1 and selected bond lengths and angles are given in Table. 1. The structure of this compound is a rigid nearly planar molecule with an r.m.s. deviation of 0.03 Å for the ten atoms making up the 1,8-naphthyridine ring. The least square plane calculated from the atoms of the acetyl amino group make an dihedral angle of 11.7 (2) ° to the least square plane of the 1,8-naphthyridine ring All bond distances are essentially identical to those found in the literature (Catalano et al., 2000).

Related literature top

For related literature, see: Bergerhoff (1996); Bruker (2000); Catalano et al. (2000); Chen et al. (2001); Ferrarini et al. (1997, 2000); He & Lippard (2001); Henry & Hammond (1977); Mogilaiah et al. (2001); Nakatani et al. (2000); Roma et al. (2000); Saito et al. (2001).

Experimental top

2-amino-5, 7-Dimethyl-1, 8-naphthyridine (Henry et al., 1977) (4.0 g, 0.10 mol) was added to a Ac2O (15 ml) solution under an atmosphere of N2. After the solution was stirred at reflux temperature for 1 h, excess solvent was removed and the final product was obtained following flash chromatography. Then, the compound was dissolved in CH2Cl2 and recrystallized by slow diffusion of aether into the CH2Cl2 solution. Yellow crystals suitable for X-ray diffraction were obtained.

Refinement top

All H atoms were placed in calculated positions. The H atoms were then constrained to an ideal geometry with C—H distances of 0.93–0.96 Å, Uiso(H) = 1.2Ueq(C) and N—H distance of 0.86 Å with Uiso(H) = 1.2Ueq(N).

Structure description top

The 1,8-naphthyridine compounds have been the focus of studies and practical applications as antibacterial agents (Mogilaiah et al., 2001). Recent parallels in biological activity of this class of compounds have been found in the form of antibacterial (Chen et al., 2001), antiinflammatory (Roma et al., 2000), antihypertensive (Ferrarini et al., 2000), and antiplatelet activity (Ferrarini et al., 1997). In addition to medicinal applications, this class of compounds have been employed in the study of bioorganic and bioorganometallic processes (Saito et al., 2001; He et al., 2001; Nakatani et al., 2000). The structure of the C12H13N3O in (I) is shown in Fig. 1 and selected bond lengths and angles are given in Table. 1. The structure of this compound is a rigid nearly planar molecule with an r.m.s. deviation of 0.03 Å for the ten atoms making up the 1,8-naphthyridine ring. The least square plane calculated from the atoms of the acetyl amino group make an dihedral angle of 11.7 (2) ° to the least square plane of the 1,8-naphthyridine ring All bond distances are essentially identical to those found in the literature (Catalano et al., 2000).

For related literature, see: Bergerhoff (1996); Bruker (2000); Catalano et al. (2000); Chen et al. (2001); Ferrarini et al. (1997, 2000); He & Lippard (2001); Henry & Hammond (1977); Mogilaiah et al. (2001); Nakatani et al. (2000); Roma et al. (2000); Saito et al. (2001).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Bergerhoff, 1996) and XP (Bruker, 2000); software used to prepare material for publication: SHELXTL (Sheldrick, 2000).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound drawn with DIAMOND (Bergerhoff, 1996). Displacement ellipsoids at the 30% probability level.
[Figure 2] Fig. 2. The packing of the title compound viewed along the c axis, drawn with XP (Bruker, 2000). H atoms have been omitted. The molecules shown are centered around z=0.0.
7-Acetylamino-2,4-dimethyl-1,8-naphthyridine top
Crystal data top
C12H13N3OF(000) = 456.0
Mr = 215.25Dx = 1.288 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1274 reflections
a = 7.970 (8) Åθ = 2.7–25.2°
b = 7.309 (7) ŵ = 0.09 mm−1
c = 19.071 (18) ÅT = 298 K
β = 91.883 (14)°Block, pale yellow
V = 1110.4 (18) Å30.52 × 0.36 × 0.24 mm
Z = 4
Data collection top
SMART 1K CCD
diffractometer		1959 independent reflections
Radiation source: fine-focus sealed tube1169 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
Detector resolution: 10 pixels mm-1θmax = 25.0°, θmin = 2.1°
φ and ω scansh = −9→9
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)		k = −8→8
Tmin = 0.970, Tmax = 0.980l = −18→22
5375 measured 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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0724P)2 + 0.2527P]
where P = (Fo2 + 2Fc2)/3
1959 reflections(Δ/σ)max < 0.001
145 parametersΔρmax = 0.27 e Å−3
0 restraintsΔρmin = −0.19 e Å−3
Crystal data top
C12H13N3OV = 1110.4 (18) Å3
Mr = 215.25Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.970 (8) ŵ = 0.09 mm−1
b = 7.309 (7) ÅT = 298 K
c = 19.071 (18) Å0.52 × 0.36 × 0.24 mm
β = 91.883 (14)°
Data collection top
SMART 1K CCD
diffractometer		1959 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)		1169 reflections with I > 2σ(I)
Tmin = 0.970, Tmax = 0.980Rint = 0.036
5375 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.153H-atom parameters constrained
S = 1.02Δρmax = 0.27 e Å−3
1959 reflectionsΔρmin = −0.19 e Å−3
145 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
N10.8038 (2)0.1591 (3)0.16857 (10)0.0416 (5)
N20.6692 (2)−0.1164 (3)0.15749 (10)0.0443 (6)
N30.9292 (3)0.4340 (3)0.18935 (10)0.0483 (6)
H30.89560.41990.23140.058*
O11.0871 (3)0.6171 (3)0.12288 (10)0.0856 (8)
C10.7455 (3)0.0253 (3)0.12480 (11)0.0391 (6)
C20.6113 (3)−0.2514 (4)0.11782 (13)0.0480 (7)
C30.6280 (3)−0.2537 (4)0.04464 (14)0.0546 (7)
H3A0.5891−0.35460.01920.066*
C40.6991 (3)−0.1130 (4)0.01004 (12)0.0472 (7)
C50.7602 (3)0.0348 (3)0.05134 (12)0.0410 (6)
C60.8324 (3)0.1936 (4)0.02437 (13)0.0498 (7)
H60.84250.2063−0.02380.060*
C70.8875 (3)0.3283 (4)0.06768 (13)0.0519 (7)
H70.93310.43510.04990.062*
C80.8742 (3)0.3032 (3)0.14080 (12)0.0415 (6)
C90.5235 (4)−0.4030 (4)0.15366 (15)0.0654 (8)
H9A0.5582−0.40540.20230.098*
H9B0.5514−0.51730.13220.098*
H9C0.4045−0.38390.14960.098*
C100.7102 (4)−0.1127 (4)−0.06836 (13)0.0670 (9)
H10A0.6876−0.2334−0.08610.100*
H10B0.8208−0.0758−0.08090.100*
H10C0.6291−0.0287−0.08820.100*
C111.0292 (3)0.5810 (4)0.17874 (14)0.0531 (7)
C121.0655 (4)0.6957 (4)0.24196 (16)0.0728 (9)
H12A1.16890.76050.23640.109*
H12B1.07490.61880.28270.109*
H12C0.97590.78180.24750.109*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0491 (12)0.0434 (12)0.0325 (11)−0.0017 (10)0.0048 (9)0.0003 (10)
N20.0509 (12)0.0426 (13)0.0394 (12)0.0014 (10)0.0001 (9)0.0032 (10)
N30.0605 (13)0.0505 (14)0.0348 (11)−0.0094 (11)0.0131 (10)−0.0031 (10)
O10.1048 (17)0.1011 (18)0.0518 (13)−0.0489 (14)0.0190 (12)0.0028 (12)
C10.0413 (13)0.0436 (15)0.0323 (13)0.0071 (11)0.0007 (10)−0.0007 (11)
C20.0502 (15)0.0443 (16)0.0490 (16)0.0052 (12)−0.0052 (13)0.0001 (13)
C30.0593 (17)0.0520 (18)0.0515 (17)0.0047 (14)−0.0120 (14)−0.0105 (14)
C40.0478 (15)0.0560 (17)0.0376 (14)0.0117 (13)−0.0033 (11)−0.0068 (13)
C50.0408 (13)0.0503 (16)0.0318 (13)0.0076 (12)0.0005 (10)0.0005 (12)
C60.0562 (15)0.0649 (18)0.0285 (13)0.0037 (14)0.0053 (11)0.0025 (13)
C70.0626 (17)0.0556 (17)0.0381 (14)−0.0031 (14)0.0096 (12)0.0073 (13)
C80.0463 (14)0.0448 (15)0.0339 (13)0.0024 (12)0.0073 (11)0.0011 (12)
C90.073 (2)0.0542 (19)0.069 (2)−0.0094 (15)−0.0014 (16)0.0020 (15)
C100.078 (2)0.085 (2)0.0372 (15)0.0111 (17)−0.0053 (14)−0.0135 (15)
C110.0555 (16)0.0564 (18)0.0479 (16)−0.0107 (14)0.0118 (13)0.0033 (14)
C120.087 (2)0.068 (2)0.065 (2)−0.0249 (18)0.0199 (16)−0.0170 (16)
Geometric parameters (Å, º) top
N1—C81.313 (3)C5—C61.401 (3)
N1—C11.357 (3)C6—C71.349 (4)
N2—C21.318 (3)C6—H60.9300
N2—C11.363 (3)C7—C81.414 (3)
N3—C111.357 (3)C7—H70.9300
N3—C81.392 (3)C9—H9A0.9600
N3—H30.8600C9—H9B0.9600
O1—C111.204 (3)C9—H9C0.9600
C1—C51.411 (3)C10—H10A0.9600
C2—C31.406 (4)C10—H10B0.9600
C2—C91.488 (4)C10—H10C0.9600
C3—C41.356 (4)C11—C121.489 (4)
C3—H3A0.9300C12—H12A0.9600
C4—C51.414 (3)C12—H12B0.9600
C4—C101.501 (4)C12—H12C0.9600
C8—N1—C1118.2 (2)C8—C7—H7120.8
C2—N2—C1117.4 (2)N1—C8—N3114.4 (2)
C11—N3—C8128.2 (2)N1—C8—C7123.3 (2)
C11—N3—H3115.9N3—C8—C7122.3 (2)
C8—N3—H3115.9C2—C9—H9A109.5
N1—C1—N2114.5 (2)C2—C9—H9B109.5
N1—C1—C5122.5 (2)H9A—C9—H9B109.5
N2—C1—C5123.0 (2)C2—C9—H9C109.5
N2—C2—C3122.4 (2)H9A—C9—H9C109.5
N2—C2—C9117.0 (2)H9B—C9—H9C109.5
C3—C2—C9120.5 (2)C4—C10—H10A109.5
C4—C3—C2121.9 (2)C4—C10—H10B109.5
C4—C3—H3A119.0H10A—C10—H10B109.5
C2—C3—H3A119.0C4—C10—H10C109.5
C3—C4—C5116.7 (2)H10A—C10—H10C109.5
C3—C4—C10121.7 (2)H10B—C10—H10C109.5
C5—C4—C10121.6 (3)O1—C11—N3123.3 (3)
C6—C5—C1117.0 (2)O1—C11—C12121.6 (3)
C6—C5—C4124.5 (2)N3—C11—C12115.1 (2)
C1—C5—C4118.5 (2)C11—C12—H12A109.5
C7—C6—C5120.6 (2)C11—C12—H12B109.5
C7—C6—H6119.7H12A—C12—H12B109.5
C5—C6—H6119.7C11—C12—H12C109.5
C6—C7—C8118.4 (2)H12A—C12—H12C109.5
C6—C7—H7120.8H12B—C12—H12C109.5

Experimental details

Crystal data
Chemical formulaC12H13N3O
Mr215.25
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)7.970 (8), 7.309 (7), 19.071 (18)
β (°) 91.883 (14)
V (Å3)1110.4 (18)
Z4
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.52 × 0.36 × 0.24
Data collection
DiffractometerSMART 1K CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2002)
Tmin, Tmax0.970, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections		5375, 1959, 1169
Rint0.036
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.153, 1.02
No. of reflections1959
No. of parameters145
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.27, −0.19

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), DIAMOND (Bergerhoff, 1996) and XP (Bruker, 2000), SHELXTL (Sheldrick, 2000).

Selected geometric parameters (Å, º) top
N1—C81.313 (3)N3—C111.357 (3)
N1—C11.357 (3)N3—C81.392 (3)
N2—C21.318 (3)O1—C111.204 (3)
N2—C11.363 (3)
C8—N1—C1118.2 (2)N2—C2—C3122.4 (2)
C2—N2—C1117.4 (2)N2—C2—C9117.0 (2)
C11—N3—C8128.2 (2)N1—C8—N3114.4 (2)
C11—N3—H3115.9N1—C8—C7123.3 (2)
C8—N3—H3115.9N3—C8—C7122.3 (2)
N1—C1—N2114.5 (2)O1—C11—N3123.3 (3)
N1—C1—C5122.5 (2)O1—C11—C12121.6 (3)
N2—C1—C5123.0 (2)N3—C11—C12115.1 (2)
 

Acknowledgements

We are grateful to the NSFC/RGC Joint Research Foundation (50418010) and a State Key Project (No. 2005CCA06800) for financial support.

References

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ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o112
https://doi.org/10.1107/S1600536807042948
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