N-(7-Methyl-1,8-naphthyridin-2-yl)acetamide-acetic acid (1/1).

In the title adduct, C11H11N3O·C2H4O2, all non-H atoms of the acetamide mol-ecule are roughly coplanar, with an r.m.s. deviation of 0.0720 Å. The dihedral angle between the ring plane and the acetamide group is 8.5 (2)°. In the crystal, O-H⋯N and N-H⋯O hydrogen bonds link the acetamide and acetic acid mol-ecules.

Related literature

For the synthesis of 7-amino-2-methyl-1,8-naphthyridine, see: Brown (1965 ▶); Henry & Hammond (1977 ▶). For the coordination modes of 1,8-naphthyridine ligands, see: Zong et al. (2004 ▶); Zúñiga et al. (2011 ▶); Li et al. (2011 ▶); Gan et al. (2011 ▶). For their biological activity, see: Sivakumar et al. (2011 ▶); Roma et al. (2000 ▶); Badawneh et al. (2001 ▶); Nagasawa et al. (2011 ▶); Capozzi et al. (2012 ▶).

Experimental

Crystal data

C11H11N3O·C2H4O2

M = 261.28

Triclinic,

a = 8.3628 (17) Å

b = 9.0904 (18) Å

c = 9.5093 (19) Å

α = 71.30 (3)°

β = 76.43 (3)°

γ = 78.64 (3)°

V = 659.8 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.15 × 0.10 × 0.07 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.986, T max = 0.993

5757 measured reflections

2591 independent reflections

1014 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.160

S = 0.91

2591 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813005242/qm2092sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005242/qm2092Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005242/qm2092Isup3.cml

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

C11H11N3O·C2H4O2	Z = 2
Mr = 261.28	F(000) = 276
Triclinic, P1	Dx = 1.315 Mg m−3
a = 8.3628 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.0904 (18) Å	Cell parameters from 25 reflections
c = 9.5093 (19) Å	θ = 3.1–26.0°
α = 71.30 (3)°	µ = 0.10 mm−1
β = 76.43 (3)°	T = 293 K
γ = 78.64 (3)°	Flaky, yellow
V = 659.8 (2) Å3	0.15 × 0.10 × 0.07 mm

Rigaku R-AXIS RAPID diffractometer	2591 independent reflections
Radiation source: fine-focus sealed tube	1014 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
ω scans	θmax = 26.0°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.986, Tmax = 0.993	k = −11→10
5757 measured reflections	l = −11→11

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H-atom parameters constrained
S = 0.91	w = 1/[σ2(Fo2) + (0.0724P)2] where P = (Fo2 + 2Fc2)/3
2591 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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
N2	0.0316 (3)	0.2121 (2)	0.5279 (2)	0.0452 (6)
N3	0.2361 (3)	0.1068 (3)	0.3663 (3)	0.0504 (7)
O3	0.9707 (3)	−0.5868 (2)	0.2515 (2)	0.0681 (7)
H3A	0.9822	−0.6417	0.3366	0.102*
C6	0.1937 (4)	−0.0352 (3)	0.6338 (3)	0.0449 (8)
C10	0.1549 (4)	0.0928 (3)	0.5099 (3)	0.0462 (8)
C3	−0.0509 (4)	0.2067 (3)	0.6651 (3)	0.0476 (8)
C4	−0.0218 (4)	0.0819 (3)	0.7965 (3)	0.0551 (9)
H4A	−0.0838	0.0818	0.8915	0.066*
O2	0.7624 (3)	−0.4612 (2)	0.3776 (3)	0.0735 (8)
C5	0.1006 (4)	−0.0375 (3)	0.7772 (3)	0.0541 (9)
H5A	0.1223	−0.1213	0.8603	0.065*
N1	−0.1743 (3)	0.3336 (3)	0.6728 (3)	0.0537 (8)
H1A	−0.1948	0.3949	0.5872	0.064*
O1	−0.2586 (3)	0.2989 (3)	0.9261 (2)	0.0799 (8)
C7	0.3229 (4)	−0.1511 (3)	0.6026 (4)	0.0559 (9)
H7A	0.3533	−0.2369	0.6808	0.067*
C12	0.8447 (4)	−0.4767 (3)	0.2609 (4)	0.0577 (9)
C8	0.4028 (4)	−0.1383 (3)	0.4598 (4)	0.0564 (9)
H8A	0.4878	−0.2153	0.4384	0.068*
C1	−0.3839 (4)	0.5235 (3)	0.7581 (3)	0.0659 (10)
H1B	−0.4453	0.5463	0.8492	0.099*
H1C	−0.4594	0.5117	0.7016	0.099*
H1D	−0.3215	0.6079	0.6984	0.099*
C9	0.3559 (4)	−0.0064 (3)	0.3426 (3)	0.0504 (8)
C11	0.4429 (5)	0.0117 (4)	0.1835 (4)	0.0734 (11)
H11A	0.3959	0.1073	0.1191	0.110*
H11B	0.4302	−0.0754	0.1526	0.110*
H11C	0.5587	0.0150	0.1761	0.110*
C2	−0.2675 (4)	0.3748 (3)	0.7971 (4)	0.0549 (9)
C13	0.8161 (5)	−0.3725 (4)	0.1088 (4)	0.0802 (12)
H13A	0.7230	−0.2939	0.1209	0.120*
H13B	0.7938	−0.4339	0.0519	0.120*
H13C	0.9131	−0.3229	0.0561	0.120*

	U11	U22	U33	U12	U13	U23
N2	0.0466 (16)	0.0427 (13)	0.0422 (14)	0.0025 (11)	−0.0123 (12)	−0.0088 (10)
N3	0.0497 (17)	0.0534 (14)	0.0479 (15)	−0.0011 (13)	−0.0106 (13)	−0.0165 (11)
O3	0.0696 (17)	0.0648 (13)	0.0544 (14)	0.0067 (12)	−0.0116 (12)	−0.0051 (10)
C6	0.049 (2)	0.0403 (15)	0.0454 (17)	0.0008 (14)	−0.0183 (15)	−0.0089 (13)
C10	0.046 (2)	0.0418 (16)	0.0518 (19)	0.0017 (14)	−0.0195 (16)	−0.0124 (14)
C3	0.050 (2)	0.0474 (16)	0.0463 (18)	0.0025 (14)	−0.0161 (15)	−0.0150 (13)
C4	0.069 (2)	0.0499 (16)	0.0403 (16)	0.0040 (16)	−0.0168 (16)	−0.0073 (13)
O2	0.0814 (19)	0.0733 (15)	0.0530 (15)	0.0150 (13)	−0.0145 (14)	−0.0142 (12)
C5	0.063 (2)	0.0435 (16)	0.0499 (19)	0.0003 (15)	−0.0160 (17)	−0.0061 (13)
N1	0.0588 (19)	0.0493 (13)	0.0455 (14)	0.0120 (13)	−0.0159 (13)	−0.0103 (11)
O1	0.093 (2)	0.0765 (15)	0.0464 (14)	0.0227 (14)	−0.0069 (12)	−0.0092 (11)
C7	0.055 (2)	0.0464 (17)	0.063 (2)	0.0073 (15)	−0.0226 (17)	−0.0115 (14)
C12	0.061 (2)	0.0537 (18)	0.052 (2)	−0.0009 (17)	−0.0167 (18)	−0.0058 (15)
C8	0.054 (2)	0.0514 (17)	0.065 (2)	0.0060 (16)	−0.0167 (18)	−0.0213 (15)
C1	0.062 (2)	0.0562 (19)	0.063 (2)	0.0124 (17)	−0.0070 (18)	−0.0096 (16)
C9	0.047 (2)	0.0543 (18)	0.0519 (19)	−0.0030 (15)	−0.0084 (16)	−0.0209 (15)
C11	0.068 (3)	0.079 (2)	0.070 (2)	0.007 (2)	−0.007 (2)	−0.0303 (18)
C2	0.052 (2)	0.0570 (18)	0.0480 (19)	0.0035 (16)	−0.0085 (16)	−0.0122 (15)
C13	0.083 (3)	0.076 (2)	0.064 (2)	0.000 (2)	−0.024 (2)	0.0049 (18)

N2—C3	1.315 (3)	O1—C2	1.211 (3)
N2—C10	1.365 (3)	C7—C8	1.344 (4)
N3—C9	1.322 (3)	C7—H7A	0.9300
N3—C10	1.353 (3)	C12—C13	1.497 (4)
O3—C12	1.310 (3)	C8—C9	1.413 (4)
O3—H3A	0.8200	C8—H8A	0.9300
C6—C5	1.399 (4)	C1—C2	1.498 (4)
C6—C7	1.402 (4)	C1—H1B	0.9600
C6—C10	1.414 (3)	C1—H1C	0.9600
C3—N1	1.397 (3)	C1—H1D	0.9600
C3—C4	1.426 (4)	C9—C11	1.489 (4)
C4—C5	1.364 (4)	C11—H11A	0.9600
C4—H4A	0.9300	C11—H11B	0.9600
O2—C12	1.195 (3)	C11—H11C	0.9600
C5—H5A	0.9300	C13—H13A	0.9600
N1—C2	1.371 (3)	C13—H13B	0.9600
N1—H1A	0.8600	C13—H13C	0.9600
C3—N2—C10	118.3 (2)	C7—C8—C9	119.2 (3)
C9—N3—C10	117.6 (2)	C7—C8—H8A	120.4
C12—O3—H3A	109.5	C9—C8—H8A	120.4
C5—C6—C7	125.0 (3)	C2—C1—H1B	109.5
C5—C6—C10	118.0 (2)	C2—C1—H1C	109.5
C7—C6—C10	117.0 (3)	H1B—C1—H1C	109.5
N3—C10—N2	115.3 (2)	C2—C1—H1D	109.5
N3—C10—C6	123.0 (2)	H1B—C1—H1D	109.5
N2—C10—C6	121.7 (3)	H1C—C1—H1D	109.5
N2—C3—N1	114.4 (2)	N3—C9—C8	123.1 (3)
N2—C3—C4	124.0 (2)	N3—C9—C11	116.5 (3)
N1—C3—C4	121.7 (3)	C8—C9—C11	120.4 (3)
C5—C4—C3	117.3 (3)	C9—C11—H11A	109.5
C5—C4—H4A	121.3	C9—C11—H11B	109.5
C3—C4—H4A	121.3	H11A—C11—H11B	109.5
C4—C5—C6	120.7 (3)	C9—C11—H11C	109.5
C4—C5—H5A	119.7	H11A—C11—H11C	109.5
C6—C5—H5A	119.7	H11B—C11—H11C	109.5
C2—N1—C3	129.4 (2)	O1—C2—N1	124.0 (3)
C2—N1—H1A	115.3	O1—C2—C1	122.8 (3)
C3—N1—H1A	115.3	N1—C2—C1	113.3 (3)
C8—C7—C6	120.1 (3)	C12—C13—H13A	109.5
C8—C7—H7A	120.0	C12—C13—H13B	109.5
C6—C7—H7A	120.0	H13A—C13—H13B	109.5
O2—C12—O3	123.8 (3)	C12—C13—H13C	109.5
O2—C12—C13	123.9 (3)	H13A—C13—H13C	109.5
O3—C12—C13	112.2 (3)	H13B—C13—H13C	109.5
C9—N3—C10—N2	−179.5 (3)	C7—C6—C5—C4	179.3 (3)
C9—N3—C10—C6	0.7 (4)	C10—C6—C5—C4	−1.1 (5)
C3—N2—C10—N3	−179.2 (3)	N2—C3—N1—C2	−170.8 (3)
C3—N2—C10—C6	0.6 (4)	C4—C3—N1—C2	10.3 (5)
C5—C6—C10—N3	−179.7 (3)	C5—C6—C7—C8	179.0 (3)
C7—C6—C10—N3	0.0 (4)	C10—C6—C7—C8	−0.6 (5)
C5—C6—C10—N2	0.6 (4)	C6—C7—C8—C9	0.6 (5)
C7—C6—C10—N2	−179.8 (3)	C10—N3—C9—C8	−0.7 (4)
C10—N2—C3—N1	179.9 (3)	C10—N3—C9—C11	179.8 (3)
C10—N2—C3—C4	−1.3 (5)	C7—C8—C9—N3	0.0 (5)
N2—C3—C4—C5	0.8 (5)	C7—C8—C9—C11	179.5 (3)
N1—C3—C4—C5	179.5 (3)	C3—N1—C2—O1	−2.5 (5)
C3—C4—C5—C6	0.5 (5)	C3—N1—C2—C1	177.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N2i	0.82	1.96	2.774 (3)	173
N1—H1A···O2ii	0.86	2.07	2.931 (3)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N2i	0.82	1.96	2.774 (3)	173
N1—H1A⋯O2ii	0.86	2.07	2.931 (3)	178

Symmetry codes: (i) ; (ii) .