7-Hy-droxy-methyl-2-pivaloyl-amino-1,8-naphthyridine.

In the title compound, C14H17N3O2, the mean plane of the 1,8-naphthyridine ring system (r.m.s deviation = 0.020 Å) forms a dihedral angle of 23.4 (1)° with the acetamide moiety (r.m.s deviation = 0.001 Å). The mol-ecular structure is stabilized by an intra-molecular O-H⋯N hydrogen bond, which generates an S(5) ring motif. In the crystal, mol-ecules are linked into inversion dimers by pairs of N-H⋯O hydrogen bonds, generating 18-membered R 2 (2)(18) ring motifs.

Related literature

For general background to and the medicinal properties of 1,8-naphthyridine derivatives see: Badawneh et al. (2001 ▶); Litvinov (2004 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H17N3O2

M = 259.31

Monoclinic,

a = 14.7026 (3) Å

b = 6.2586 (1) Å

c = 14.7035 (3) Å

β = 97.447 (2)°

V = 1341.57 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 297 K

0.51 × 0.46 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.956, T max = 0.993

20410 measured reflections

3949 independent reflections

2551 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.148

S = 1.14

3949 reflections

183 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813005527/rz5047sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005527/rz5047Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005527/rz5047Isup3.cml

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

C14H17N3O2	F(000) = 552
Mr = 259.31	Dx = 1.284 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4518 reflections
a = 14.7026 (3) Å	θ = 2.8–30.1°
b = 6.2586 (1) Å	µ = 0.09 mm−1
c = 14.7035 (3) Å	T = 297 K
β = 97.447 (2)°	Plate, brown
V = 1341.57 (4) Å3	0.51 × 0.46 × 0.08 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3949 independent reflections
Radiation source: fine-focus sealed tube	2551 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
φ and ω scans	θmax = 30.2°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −20→20
Tmin = 0.956, Tmax = 0.993	k = −8→8
20410 measured reflections	l = −20→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ2(Fo2) + (0.0366P)2 + 0.506P] where P = (Fo2 + 2Fc2)/3
3949 reflections	(Δ/σ)max = 0.001
183 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.70708 (11)	−0.0049 (3)	0.72243 (11)	0.0731 (5)
O2	1.20193 (11)	0.4754 (2)	0.50680 (10)	0.0564 (4)
N1	0.93270 (10)	0.1958 (2)	0.60449 (9)	0.0398 (4)
N2	1.08422 (10)	0.2310 (2)	0.58087 (9)	0.0403 (4)
C1	1.01722 (12)	0.1059 (3)	0.60905 (10)	0.0369 (4)
C2	1.16763 (13)	0.1520 (3)	0.58648 (11)	0.0424 (4)
C3	1.19173 (15)	−0.0552 (3)	0.61930 (12)	0.0509 (5)
H3A	1.2519	−0.1032	0.6226	0.061*
C4	1.12550 (14)	−0.1827 (3)	0.64593 (12)	0.0495 (5)
H4A	1.1396	−0.3206	0.6668	0.059*
C5	1.03554 (13)	−0.1052 (3)	0.64177 (11)	0.0410 (4)
C6	0.96182 (14)	−0.2230 (3)	0.66823 (11)	0.0468 (5)
H6A	0.9707	−0.3639	0.6876	0.056*
C7	0.87830 (14)	−0.1325 (3)	0.66566 (12)	0.0475 (5)
H7A	0.8296	−0.2073	0.6850	0.057*
C8	0.86672 (13)	0.0803 (3)	0.63253 (11)	0.0406 (4)
N3	0.78116 (12)	0.1817 (3)	0.62256 (12)	0.0490 (4)
C9	0.70570 (14)	0.1334 (3)	0.66391 (14)	0.0505 (5)
C10	0.61984 (14)	0.2648 (3)	0.63154 (15)	0.0578 (6)
C11	0.59481 (17)	0.2364 (5)	0.52733 (18)	0.0814 (8)
H11A	0.5892	0.0869	0.5130	0.122*
H11B	0.6420	0.2979	0.4962	0.122*
H11C	0.5376	0.3066	0.5077	0.122*
C12	0.54109 (18)	0.1846 (5)	0.6811 (2)	0.0986 (10)
H12A	0.5286	0.0376	0.6656	0.148*
H12B	0.4872	0.2687	0.6627	0.148*
H12C	0.5580	0.1973	0.7462	0.148*
C13	0.63721 (16)	0.5019 (4)	0.65370 (17)	0.0688 (6)
H13A	0.6540	0.5190	0.7186	0.103*
H13B	0.5824	0.5822	0.6344	0.103*
H13C	0.6860	0.5530	0.6220	0.103*
C14	1.23927 (14)	0.2947 (3)	0.55470 (14)	0.0536 (5)
H14A	1.2810	0.3412	0.6075	0.064*
H14B	1.2745	0.2136	0.5152	0.064*
H1N3	0.7793 (14)	0.288 (4)	0.5889 (14)	0.057 (6)*
H1O2	1.1439 (18)	0.474 (4)	0.5097 (18)	0.087 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0823 (11)	0.0626 (10)	0.0797 (11)	−0.0054 (9)	0.0311 (9)	0.0198 (9)
O2	0.0555 (9)	0.0436 (8)	0.0725 (10)	0.0026 (7)	0.0170 (8)	0.0102 (7)
N1	0.0502 (9)	0.0312 (8)	0.0379 (7)	0.0001 (7)	0.0052 (6)	0.0041 (6)
N2	0.0505 (9)	0.0323 (8)	0.0381 (7)	0.0023 (7)	0.0061 (6)	0.0028 (6)
C1	0.0543 (11)	0.0285 (9)	0.0277 (8)	0.0023 (8)	0.0041 (7)	−0.0003 (7)
C2	0.0531 (11)	0.0408 (10)	0.0333 (8)	0.0059 (9)	0.0058 (8)	−0.0014 (7)
C3	0.0610 (13)	0.0464 (12)	0.0453 (10)	0.0178 (10)	0.0074 (9)	0.0020 (9)
C4	0.0760 (14)	0.0356 (10)	0.0373 (9)	0.0169 (10)	0.0082 (9)	0.0056 (8)
C5	0.0648 (12)	0.0305 (9)	0.0276 (8)	0.0050 (8)	0.0060 (8)	−0.0004 (7)
C6	0.0770 (14)	0.0275 (9)	0.0354 (9)	0.0005 (9)	0.0058 (9)	0.0041 (7)
C7	0.0673 (13)	0.0343 (10)	0.0415 (10)	−0.0090 (9)	0.0087 (9)	0.0036 (8)
C8	0.0524 (11)	0.0351 (9)	0.0339 (8)	−0.0032 (8)	0.0035 (8)	−0.0002 (7)
N3	0.0524 (10)	0.0409 (9)	0.0547 (10)	−0.0029 (8)	0.0105 (8)	0.0112 (8)
C9	0.0579 (12)	0.0413 (11)	0.0538 (11)	−0.0123 (9)	0.0132 (9)	−0.0048 (9)
C10	0.0519 (12)	0.0484 (12)	0.0749 (14)	−0.0070 (10)	0.0151 (11)	−0.0055 (11)
C11	0.0617 (15)	0.0837 (19)	0.0930 (18)	0.0035 (13)	−0.0122 (13)	−0.0208 (15)
C12	0.0694 (17)	0.084 (2)	0.152 (3)	−0.0073 (15)	0.0491 (18)	0.009 (2)
C13	0.0699 (15)	0.0540 (14)	0.0838 (16)	−0.0001 (12)	0.0141 (12)	−0.0100 (12)
C14	0.0532 (12)	0.0512 (12)	0.0571 (12)	0.0051 (10)	0.0094 (9)	0.0030 (10)

O1—C9	1.219 (2)	C8—N3	1.399 (2)
O2—C14	1.406 (2)	N3—C9	1.366 (2)
O2—H1O2	0.86 (3)	N3—H1N3	0.83 (2)
N1—C8	1.318 (2)	C9—C10	1.530 (3)
N1—C1	1.358 (2)	C10—C12	1.531 (3)
N2—C2	1.315 (2)	C10—C13	1.534 (3)
N2—C1	1.364 (2)	C10—C11	1.539 (3)
C1—C5	1.420 (2)	C11—H11A	0.9600
C2—C3	1.412 (3)	C11—H11B	0.9600
C2—C14	1.501 (3)	C11—H11C	0.9600
C3—C4	1.356 (3)	C12—H12A	0.9600
C3—H3A	0.9300	C12—H12B	0.9600
C4—C5	1.403 (3)	C12—H12C	0.9600
C4—H4A	0.9300	C13—H13A	0.9600
C5—C6	1.407 (3)	C13—H13B	0.9600
C6—C7	1.348 (3)	C13—H13C	0.9600
C6—H6A	0.9300	C14—H14A	0.9700
C7—C8	1.421 (3)	C14—H14B	0.9700
C7—H7A	0.9300
C14—O2—H1O2	106.9 (18)	N3—C9—C10	115.32 (18)
C8—N1—C1	117.60 (15)	C9—C10—C12	108.7 (2)
C2—N2—C1	117.98 (15)	C9—C10—C13	110.25 (18)
N1—C1—N2	116.06 (15)	C12—C10—C13	109.4 (2)
N1—C1—C5	122.31 (17)	C9—C10—C11	109.20 (18)
N2—C1—C5	121.63 (16)	C12—C10—C11	109.8 (2)
N2—C2—C3	123.87 (18)	C13—C10—C11	109.6 (2)
N2—C2—C14	116.29 (16)	C10—C11—H11A	109.5
C3—C2—C14	119.83 (17)	C10—C11—H11B	109.5
C4—C3—C2	118.79 (18)	H11A—C11—H11B	109.5
C4—C3—H3A	120.6	C10—C11—H11C	109.5
C2—C3—H3A	120.6	H11A—C11—H11C	109.5
C3—C4—C5	119.48 (17)	H11B—C11—H11C	109.5
C3—C4—H4A	120.3	C10—C12—H12A	109.5
C5—C4—H4A	120.3	C10—C12—H12B	109.5
C4—C5—C6	124.22 (17)	H12A—C12—H12B	109.5
C4—C5—C1	118.24 (17)	C10—C12—H12C	109.5
C6—C5—C1	117.54 (17)	H12A—C12—H12C	109.5
C7—C6—C5	120.21 (17)	H12B—C12—H12C	109.5
C7—C6—H6A	119.9	C10—C13—H13A	109.5
C5—C6—H6A	119.9	C10—C13—H13B	109.5
C6—C7—C8	118.16 (18)	H13A—C13—H13B	109.5
C6—C7—H7A	120.9	C10—C13—H13C	109.5
C8—C7—H7A	120.9	H13A—C13—H13C	109.5
N1—C8—N3	113.99 (16)	H13B—C13—H13C	109.5
N1—C8—C7	124.12 (18)	O2—C14—C2	112.97 (16)
N3—C8—C7	121.81 (18)	O2—C14—H14A	109.0
C9—N3—C8	128.60 (18)	C2—C14—H14A	109.0
C9—N3—H1N3	118.5 (15)	O2—C14—H14B	109.0
C8—N3—H1N3	112.8 (15)	C2—C14—H14B	109.0
O1—C9—N3	122.1 (2)	H14A—C14—H14B	107.8
O1—C9—C10	122.61 (19)
C8—N1—C1—N2	−178.99 (14)	C5—C6—C7—C8	2.3 (3)
C8—N1—C1—C5	0.6 (2)	C1—N1—C8—N3	−177.86 (14)
C2—N2—C1—N1	178.24 (14)	C1—N1—C8—C7	−1.0 (2)
C2—N2—C1—C5	−1.3 (2)	C6—C7—C8—N1	−0.4 (3)
C1—N2—C2—C3	0.5 (2)	C6—C7—C8—N3	176.20 (16)
C1—N2—C2—C14	179.94 (15)	N1—C8—N3—C9	−162.20 (18)
N2—C2—C3—C4	0.7 (3)	C7—C8—N3—C9	20.9 (3)
C14—C2—C3—C4	−178.71 (17)	C8—N3—C9—O1	5.0 (3)
C2—C3—C4—C5	−1.1 (3)	C8—N3—C9—C10	−174.93 (18)
C3—C4—C5—C6	−179.53 (17)	O1—C9—C10—C12	−2.5 (3)
C3—C4—C5—C1	0.3 (2)	N3—C9—C10—C12	177.52 (19)
N1—C1—C5—C4	−178.57 (15)	O1—C9—C10—C13	117.4 (2)
N2—C1—C5—C4	0.9 (2)	N3—C9—C10—C13	−62.6 (2)
N1—C1—C5—C6	1.3 (2)	O1—C9—C10—C11	−122.2 (2)
N2—C1—C5—C6	−179.22 (15)	N3—C9—C10—C11	57.8 (2)
C4—C5—C6—C7	177.13 (17)	N2—C2—C14—O2	−12.0 (2)
C1—C5—C6—C7	−2.7 (2)	C3—C2—C14—O2	167.53 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···O2i	0.83 (2)	2.09 (2)	2.900 (2)	168 (2)
O2—H1O2···N2	0.86 (3)	2.10 (3)	2.648 (2)	121 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯O2i	0.83 (2)	2.09 (2)	2.900 (2)	168 (2)
O2—H1O2⋯N2	0.86 (3)	2.10 (3)	2.648 (2)	121 (2)

Symmetry code: (i) .