7-Acetyl-amino-2,4-dimethyl-1,8-naphthyridine.

The air-stable title compound, C(12)H(13)N(3)O, which is of inter-est due to its anti-bacterial properties, is an almost planar mol-ecule 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 acetyl-amino 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 ▶); 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

Crystal data

C12H13N3O

M = 215.25

Monoclinic,

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 ▶) T min = 0.970, T max = 0.980

5375 measured reflections

1959 independent reflections

1169 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 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 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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 ▶).

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807042948/er2027Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H13N3O	F000 = 456.0
Mr = 215.25	Dx = 1.288 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1274 reflections
a = 7.970 (8) Å	θ = 2.7–25.2º
b = 7.309 (7) Å	µ = 0.09 mm−1
c = 19.071 (18) Å	T = 298 (2) K
β = 91.883 (14)º	Block, pale yellow
V = 1110.4 (18) Å3	0.52 × 0.36 × 0.24 mm
Z = 4

SMART 1K CCD diffractometer	1959 independent reflections
Radiation source: fine-focus sealed tube	1169 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.036
Detector resolution: 10 pixels mm-1	θmax = 25.0º
T = 298(2) K	θmin = 2.1º
φ and ω scans	h = −9→9
Absorption correction: multi-scan(SADABS; Sheldrick, 2002)	k = −8→8
Tmin = 0.970, Tmax = 0.980	l = −18→22
5375 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H-atom parameters constrained
wR(F2) = 0.153	w = 1/[σ2(Fo2) + (0.0724P)2 + 0.2527P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
1959 reflections	Δρmax = 0.27 e Å−3
145 parameters	Δρmin = −0.19 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
N1	0.8038 (2)	0.1591 (3)	0.16857 (10)	0.0416 (5)
N2	0.6692 (2)	−0.1164 (3)	0.15749 (10)	0.0443 (6)
N3	0.9292 (3)	0.4340 (3)	0.18935 (10)	0.0483 (6)
H3	0.8956	0.4199	0.2314	0.058*
O1	1.0871 (3)	0.6171 (3)	0.12288 (10)	0.0856 (8)
C1	0.7455 (3)	0.0253 (3)	0.12480 (11)	0.0391 (6)
C2	0.6113 (3)	−0.2514 (4)	0.11782 (13)	0.0480 (7)
C3	0.6280 (3)	−0.2537 (4)	0.04464 (14)	0.0546 (7)
H3A	0.5891	−0.3546	0.0192	0.066*
C4	0.6991 (3)	−0.1130 (4)	0.01004 (12)	0.0472 (7)
C5	0.7602 (3)	0.0348 (3)	0.05134 (12)	0.0410 (6)
C6	0.8324 (3)	0.1936 (4)	0.02437 (13)	0.0498 (7)
H6	0.8425	0.2063	−0.0238	0.060*
C7	0.8875 (3)	0.3283 (4)	0.06768 (13)	0.0519 (7)
H7	0.9331	0.4351	0.0499	0.062*
C8	0.8742 (3)	0.3032 (3)	0.14080 (12)	0.0415 (6)
C9	0.5235 (4)	−0.4030 (4)	0.15366 (15)	0.0654 (8)
H9A	0.5582	−0.4054	0.2023	0.098*
H9B	0.5514	−0.5173	0.1322	0.098*
H9C	0.4045	−0.3839	0.1496	0.098*
C10	0.7102 (4)	−0.1127 (4)	−0.06836 (13)	0.0670 (9)
H10A	0.6876	−0.2334	−0.0861	0.100*
H10B	0.8208	−0.0758	−0.0809	0.100*
H10C	0.6291	−0.0287	−0.0882	0.100*
C11	1.0292 (3)	0.5810 (4)	0.17874 (14)	0.0531 (7)
C12	1.0655 (4)	0.6957 (4)	0.24196 (16)	0.0728 (9)
H12A	1.1689	0.7605	0.2364	0.109*
H12B	1.0749	0.6188	0.2827	0.109*
H12C	0.9759	0.7818	0.2475	0.109*

	U11	U22	U33	U12	U13	U23
N1	0.0491 (12)	0.0434 (12)	0.0325 (11)	−0.0017 (10)	0.0048 (9)	0.0003 (10)
N2	0.0509 (12)	0.0426 (13)	0.0394 (12)	0.0014 (10)	0.0001 (9)	0.0032 (10)
N3	0.0605 (13)	0.0505 (14)	0.0348 (11)	−0.0094 (11)	0.0131 (10)	−0.0031 (10)
O1	0.1048 (17)	0.1011 (18)	0.0518 (13)	−0.0489 (14)	0.0190 (12)	0.0028 (12)
C1	0.0413 (13)	0.0436 (15)	0.0323 (13)	0.0071 (11)	0.0007 (10)	−0.0007 (11)
C2	0.0502 (15)	0.0443 (16)	0.0490 (16)	0.0052 (12)	−0.0052 (13)	0.0001 (13)
C3	0.0593 (17)	0.0520 (18)	0.0515 (17)	0.0047 (14)	−0.0120 (14)	−0.0105 (14)
C4	0.0478 (15)	0.0560 (17)	0.0376 (14)	0.0117 (13)	−0.0033 (11)	−0.0068 (13)
C5	0.0408 (13)	0.0503 (16)	0.0318 (13)	0.0076 (12)	0.0005 (10)	0.0005 (12)
C6	0.0562 (15)	0.0649 (18)	0.0285 (13)	0.0037 (14)	0.0053 (11)	0.0025 (13)
C7	0.0626 (17)	0.0556 (17)	0.0381 (14)	−0.0031 (14)	0.0096 (12)	0.0073 (13)
C8	0.0463 (14)	0.0448 (15)	0.0339 (13)	0.0024 (12)	0.0073 (11)	0.0011 (12)
C9	0.073 (2)	0.0542 (19)	0.069 (2)	−0.0094 (15)	−0.0014 (16)	0.0020 (15)
C10	0.078 (2)	0.085 (2)	0.0372 (15)	0.0111 (17)	−0.0053 (14)	−0.0135 (15)
C11	0.0555 (16)	0.0564 (18)	0.0479 (16)	−0.0107 (14)	0.0118 (13)	0.0033 (14)
C12	0.087 (2)	0.068 (2)	0.065 (2)	−0.0249 (18)	0.0199 (16)	−0.0170 (16)

N1—C8	1.313 (3)	C5—C6	1.401 (3)
N1—C1	1.357 (3)	C6—C7	1.349 (4)
N2—C2	1.318 (3)	C6—H6	0.9300
N2—C1	1.363 (3)	C7—C8	1.414 (3)
N3—C11	1.357 (3)	C7—H7	0.9300
N3—C8	1.392 (3)	C9—H9A	0.9600
N3—H3	0.8600	C9—H9B	0.9600
O1—C11	1.204 (3)	C9—H9C	0.9600
C1—C5	1.411 (3)	C10—H10A	0.9600
C2—C3	1.406 (4)	C10—H10B	0.9600
C2—C9	1.488 (4)	C10—H10C	0.9600
C3—C4	1.356 (4)	C11—C12	1.489 (4)
C3—H3A	0.9300	C12—H12A	0.9600
C4—C5	1.414 (3)	C12—H12B	0.9600
C4—C10	1.501 (4)	C12—H12C	0.9600
C8—N1—C1	118.2 (2)	C8—C7—H7	120.8
C2—N2—C1	117.4 (2)	N1—C8—N3	114.4 (2)
C11—N3—C8	128.2 (2)	N1—C8—C7	123.3 (2)
C11—N3—H3	115.9	N3—C8—C7	122.3 (2)
C8—N3—H3	115.9	C2—C9—H9A	109.5
N1—C1—N2	114.5 (2)	C2—C9—H9B	109.5
N1—C1—C5	122.5 (2)	H9A—C9—H9B	109.5
N2—C1—C5	123.0 (2)	C2—C9—H9C	109.5
N2—C2—C3	122.4 (2)	H9A—C9—H9C	109.5
N2—C2—C9	117.0 (2)	H9B—C9—H9C	109.5
C3—C2—C9	120.5 (2)	C4—C10—H10A	109.5
C4—C3—C2	121.9 (2)	C4—C10—H10B	109.5
C4—C3—H3A	119.0	H10A—C10—H10B	109.5
C2—C3—H3A	119.0	C4—C10—H10C	109.5
C3—C4—C5	116.7 (2)	H10A—C10—H10C	109.5
C3—C4—C10	121.7 (2)	H10B—C10—H10C	109.5
C5—C4—C10	121.6 (3)	O1—C11—N3	123.3 (3)
C6—C5—C1	117.0 (2)	O1—C11—C12	121.6 (3)
C6—C5—C4	124.5 (2)	N3—C11—C12	115.1 (2)
C1—C5—C4	118.5 (2)	C11—C12—H12A	109.5
C7—C6—C5	120.6 (2)	C11—C12—H12B	109.5
C7—C6—H6	119.7	H12A—C12—H12B	109.5
C5—C6—H6	119.7	C11—C12—H12C	109.5
C6—C7—C8	118.4 (2)	H12A—C12—H12C	109.5
C6—C7—H7	120.8	H12B—C12—H12C	109.5