7-(2,2-Dimethylpropanamido)-2-methyl-1,8-naphthyridin-1-ium chloride monohydrate.

The asymmetric unit of the title compound, C(14)H(18)N(3)O(+)·Cl(-)·H(2)O, comprises a substituted amido-naphthyridine cation, a chloride anion and a water mol-ecule of crystallization. Intra-molecular C-H⋯O hydrogen bonds generate six-membered rings, producing an S(6) ring motif. The amido group is twisted from the naphthyridine ring, making a dihedral angle of 17.65 (7)°. The crystal structure is stabilized by inter-molecular N-H⋯O, N-H⋯Cl, O-H⋯Cl (× 2), and C-H⋯O (× 2) hydrogen bonds. These inter-actions linked neighbouring mol-ecules into chains along the a and b axes of the crystal, thus forming mol-ecular sheets parallel to the (001) plane.

Related literature

For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For biological activity and mol­ecular recognition, see: Goswami et al. (2005 ▶); Carmen et al. (2004 ▶); Goswami & Mukherjee (1997 ▶); Yu et al. (2008 ▶).

Experimental

Crystal data

C14H18N3O+·Cl−·H2O

M = 297.78

Orthorhombic,

a = 19.0092 (5) Å

b = 9.0077 (2) Å

c = 17.7294 (5) Å

V = 3035.79 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.26 mm−1

T = 100.0 (1) K

0.41 × 0.29 × 0.19 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.902, T max = 0.954

19927 measured reflections

4489 independent reflections

3470 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.102

S = 1.07

4489 reflections

198 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶)’; 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, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042955/ng2528sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042955/ng2528Isup2.hkl

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

C14H18N3O+·Cl−·H2O	F(000) = 1264
Mr = 297.78	Dx = 1.303 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 5042 reflections
a = 19.0092 (5) Å	θ = 2.3–29.9°
b = 9.0077 (2) Å	µ = 0.26 mm−1
c = 17.7294 (5) Å	T = 100 K
V = 3035.79 (14) Å3	Block, colourless
Z = 8	0.41 × 0.29 × 0.19 mm

Bruker SMART APEXII CCD area-detector diffractometer	4489 independent reflections
Radiation source: fine-focus sealed tube	3470 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 30.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −26→23
Tmin = 0.902, Tmax = 0.954	k = −12→12
19927 measured reflections	l = −25→18

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0453P)2 + 0.653P] where P = (Fo2 + 2Fc2)/3
4489 reflections	(Δ/σ)max = 0.001
198 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Cl1	0.613003 (17)	0.14014 (4)	0.995585 (18)	0.02130 (9)
O1	0.35100 (5)	0.43024 (11)	0.71527 (5)	0.0247 (2)
N1	0.41076 (6)	0.32279 (13)	0.81210 (7)	0.0197 (2)
N2	0.50292 (6)	0.40348 (12)	0.88207 (6)	0.0180 (2)
N3	0.59795 (6)	0.47140 (12)	0.95397 (6)	0.0174 (2)
C1	0.54282 (6)	0.51370 (14)	0.90903 (7)	0.0166 (3)
C2	0.64346 (7)	0.56681 (15)	0.98399 (7)	0.0194 (3)
C3	0.63409 (7)	0.71897 (15)	0.97088 (8)	0.0224 (3)
H3A	0.6653	0.7870	0.9918	0.027*
C4	0.57933 (7)	0.76783 (15)	0.92753 (8)	0.0218 (3)
H4A	0.5730	0.8690	0.9196	0.026*
C5	0.53258 (7)	0.66552 (14)	0.89490 (7)	0.0182 (3)
C6	0.47437 (7)	0.70180 (15)	0.84855 (8)	0.0216 (3)
H6A	0.4641	0.8006	0.8381	0.026*
C7	0.43369 (7)	0.59217 (15)	0.81942 (8)	0.0209 (3)
H7A	0.3958	0.6147	0.7883	0.025*
C8	0.45006 (7)	0.44204 (14)	0.83733 (7)	0.0178 (3)
C9	0.36274 (7)	0.32093 (15)	0.75354 (7)	0.0191 (3)
C10	0.32593 (7)	0.17247 (15)	0.74131 (7)	0.0209 (3)
C11	0.27199 (8)	0.19006 (18)	0.67779 (8)	0.0276 (3)
H11A	0.2482	0.0973	0.6698	0.041*
H11B	0.2956	0.2190	0.6323	0.041*
H11C	0.2383	0.2648	0.6914	0.041*
C12	0.28790 (8)	0.12662 (18)	0.81407 (8)	0.0288 (3)
H12A	0.3216	0.1148	0.8539	0.043*
H12B	0.2637	0.0344	0.8060	0.043*
H12C	0.2545	0.2020	0.8278	0.043*
C13	0.38030 (8)	0.05470 (16)	0.71945 (8)	0.0272 (3)
H13A	0.4136	0.0431	0.7597	0.041*
H13B	0.4044	0.0853	0.6745	0.041*
H13C	0.3569	−0.0381	0.7105	0.041*
C14	0.70189 (7)	0.50748 (17)	1.03071 (8)	0.0254 (3)
H14A	0.6971	0.4017	1.0352	0.038*
H14B	0.7003	0.5518	1.0799	0.038*
H14C	0.7460	0.5305	1.0072	0.038*
O1W	0.46432 (6)	0.07427 (12)	0.89481 (6)	0.0233 (2)
H1N1	0.4218 (9)	0.244 (2)	0.8337 (9)	0.028 (4)*
H1N3	0.6013 (9)	0.376 (2)	0.9631 (11)	0.037 (5)*
H1W1	0.4421 (10)	0.016 (2)	0.9277 (11)	0.042 (5)*
H2W1	0.4959 (11)	0.119 (2)	0.9197 (11)	0.048 (6)*

	U11	U22	U33	U12	U13	U23
Cl1	0.02288 (18)	0.01664 (16)	0.02439 (17)	−0.00058 (12)	0.00160 (12)	0.00273 (13)
O1	0.0238 (5)	0.0249 (5)	0.0254 (5)	0.0023 (4)	−0.0030 (4)	0.0028 (4)
N1	0.0191 (6)	0.0159 (6)	0.0241 (6)	−0.0016 (4)	−0.0036 (4)	0.0020 (5)
N2	0.0171 (5)	0.0146 (5)	0.0223 (5)	−0.0005 (4)	−0.0002 (4)	0.0004 (4)
N3	0.0182 (5)	0.0136 (5)	0.0204 (5)	−0.0008 (4)	0.0004 (4)	0.0003 (4)
C1	0.0163 (6)	0.0157 (6)	0.0177 (6)	0.0000 (5)	0.0027 (5)	0.0003 (5)
C2	0.0182 (6)	0.0200 (7)	0.0200 (6)	−0.0025 (5)	0.0013 (5)	−0.0020 (5)
C3	0.0232 (7)	0.0193 (7)	0.0247 (7)	−0.0064 (5)	0.0020 (5)	−0.0026 (6)
C4	0.0265 (7)	0.0146 (6)	0.0242 (7)	−0.0022 (5)	0.0039 (5)	−0.0005 (5)
C5	0.0211 (7)	0.0147 (6)	0.0187 (6)	−0.0002 (5)	0.0042 (5)	−0.0004 (5)
C6	0.0250 (7)	0.0159 (6)	0.0238 (6)	0.0027 (5)	0.0027 (5)	0.0015 (5)
C7	0.0211 (7)	0.0188 (6)	0.0228 (6)	0.0029 (5)	−0.0013 (5)	0.0018 (5)
C8	0.0163 (6)	0.0177 (6)	0.0193 (6)	0.0001 (5)	0.0022 (5)	−0.0001 (5)
C9	0.0146 (6)	0.0235 (7)	0.0191 (6)	0.0011 (5)	0.0033 (5)	−0.0016 (5)
C10	0.0187 (7)	0.0253 (7)	0.0187 (6)	−0.0052 (5)	0.0017 (5)	−0.0023 (5)
C11	0.0221 (7)	0.0360 (8)	0.0248 (7)	−0.0061 (6)	−0.0017 (6)	−0.0019 (6)
C12	0.0277 (8)	0.0362 (9)	0.0226 (7)	−0.0125 (7)	0.0037 (6)	−0.0010 (6)
C13	0.0301 (8)	0.0246 (7)	0.0270 (7)	−0.0018 (6)	0.0006 (6)	−0.0048 (6)
C14	0.0207 (7)	0.0254 (7)	0.0300 (7)	−0.0025 (6)	−0.0049 (6)	−0.0010 (6)
O1W	0.0259 (6)	0.0190 (5)	0.0251 (5)	−0.0034 (4)	−0.0011 (4)	0.0035 (4)

O1—C9	1.2164 (16)	C7—H7A	0.9300
N1—C9	1.3824 (17)	C9—C10	1.5248 (19)
N1—C8	1.3827 (17)	C10—C13	1.531 (2)
N1—H1N1	0.834 (17)	C10—C11	1.5312 (19)
N2—C8	1.3266 (17)	C10—C12	1.5353 (19)
N2—C1	1.3377 (16)	C11—H11A	0.9600
N3—C2	1.3305 (17)	C11—H11B	0.9600
N3—C1	1.3705 (17)	C11—H11C	0.9600
N3—H1N3	0.881 (18)	C12—H12A	0.9600
C1—C5	1.4039 (18)	C12—H12B	0.9600
C2—C3	1.401 (2)	C12—H12C	0.9600
C2—C14	1.4851 (19)	C13—H13A	0.9600
C3—C4	1.367 (2)	C13—H13B	0.9600
C3—H3A	0.9300	C13—H13C	0.9600
C4—C5	1.4050 (19)	C14—H14A	0.9600
C4—H4A	0.9300	C14—H14B	0.9600
C5—C6	1.4163 (19)	C14—H14C	0.9600
C6—C7	1.3565 (19)	O1W—H1W1	0.89 (2)
C6—H6A	0.9300	O1W—H2W1	0.85 (2)
C7—C8	1.4236 (18)
C9—N1—C8	127.52 (12)	N1—C9—C10	114.86 (12)
C9—N1—H1N1	120.1 (12)	C9—C10—C13	109.50 (11)
C8—N1—H1N1	112.1 (12)	C9—C10—C11	108.73 (12)
C8—N2—C1	116.67 (11)	C13—C10—C11	109.72 (11)
C2—N3—C1	123.38 (12)	C9—C10—C12	109.43 (11)
C2—N3—H1N3	120.8 (12)	C13—C10—C12	110.14 (12)
C1—N3—H1N3	115.8 (12)	C11—C10—C12	109.30 (11)
N2—C1—N3	115.78 (11)	C10—C11—H11A	109.5
N2—C1—C5	125.49 (12)	C10—C11—H11B	109.5
N3—C1—C5	118.73 (12)	H11A—C11—H11B	109.5
N3—C2—C3	118.86 (12)	C10—C11—H11C	109.5
N3—C2—C14	118.48 (12)	H11A—C11—H11C	109.5
C3—C2—C14	122.65 (13)	H11B—C11—H11C	109.5
C4—C3—C2	120.34 (13)	C10—C12—H12A	109.5
C4—C3—H3A	119.8	C10—C12—H12B	109.5
C2—C3—H3A	119.8	H12A—C12—H12B	109.5
C3—C4—C5	120.14 (13)	C10—C12—H12C	109.5
C3—C4—H4A	119.9	H12A—C12—H12C	109.5
C5—C4—H4A	119.9	H12B—C12—H12C	109.5
C1—C5—C4	118.54 (12)	C10—C13—H13A	109.5
C1—C5—C6	115.89 (12)	C10—C13—H13B	109.5
C4—C5—C6	125.57 (12)	H13A—C13—H13B	109.5
C7—C6—C5	119.89 (13)	C10—C13—H13C	109.5
C7—C6—H6A	120.1	H13A—C13—H13C	109.5
C5—C6—H6A	120.1	H13B—C13—H13C	109.5
C6—C7—C8	118.81 (13)	C2—C14—H14A	109.5
C6—C7—H7A	120.6	C2—C14—H14B	109.5
C8—C7—H7A	120.6	H14A—C14—H14B	109.5
N2—C8—N1	113.54 (12)	C2—C14—H14C	109.5
N2—C8—C7	123.21 (12)	H14A—C14—H14C	109.5
N1—C8—C7	123.21 (12)	H14B—C14—H14C	109.5
O1—C9—N1	122.02 (13)	H1W1—O1W—H2W1	106.0 (17)
O1—C9—C10	123.12 (12)
C8—N2—C1—N3	−178.82 (11)	C4—C5—C6—C7	178.98 (13)
C8—N2—C1—C5	1.12 (19)	C5—C6—C7—C8	1.0 (2)
C2—N3—C1—N2	178.57 (12)	C1—N2—C8—N1	−179.49 (11)
C2—N3—C1—C5	−1.37 (19)	C1—N2—C8—C7	−1.82 (19)
C1—N3—C2—C3	1.62 (19)	C9—N1—C8—N2	−165.13 (12)
C1—N3—C2—C14	−178.93 (12)	C9—N1—C8—C7	17.2 (2)
N3—C2—C3—C4	−0.5 (2)	C6—C7—C8—N2	0.8 (2)
C14—C2—C3—C4	−179.88 (13)	C6—C7—C8—N1	178.26 (12)
C2—C3—C4—C5	−0.9 (2)	C8—N1—C9—O1	1.8 (2)
N2—C1—C5—C4	−179.98 (12)	C8—N1—C9—C10	−177.97 (12)
N3—C1—C5—C4	−0.04 (18)	O1—C9—C10—C13	117.22 (14)
N2—C1—C5—C6	0.55 (19)	N1—C9—C10—C13	−63.06 (15)
N3—C1—C5—C6	−179.51 (11)	O1—C9—C10—C11	−2.65 (18)
C3—C4—C5—C1	1.12 (19)	N1—C9—C10—C11	177.07 (11)
C3—C4—C5—C6	−179.46 (13)	O1—C9—C10—C12	−121.97 (15)
C1—C5—C6—C7	−1.59 (18)	N1—C9—C10—C12	57.75 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1W	0.833 (18)	2.041 (17)	2.8633 (16)	169.1 (16)
N3—H1N3···Cl1	0.877 (18)	2.213 (18)	3.0870 (11)	175.2 (16)
O1W—H1W1···Cl1i	0.891 (19)	2.219 (19)	3.1091 (12)	176.5 (18)
O1W—H2W1···Cl1	0.85 (2)	2.61 (2)	3.3960 (12)	155.3 (16)
C7—H7A···O1	0.93	2.27	2.8298 (17)	118
C11—H11A···O1ii	0.96	2.54	3.3742 (18)	145
C13—H13A···O1W	0.96	2.60	3.4997 (18)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1W	0.833 (18)	2.041 (17)	2.8633 (16)	169.1 (16)
N3—H1N3⋯Cl1	0.877 (18)	2.213 (18)	3.0870 (11)	175.2 (16)
O1W—H1W1⋯Cl1i	0.891 (19)	2.219 (19)	3.1091 (12)	176.5 (18)
O1W—H2W1⋯Cl1	0.85 (2)	2.61 (2)	3.3960 (12)	155.3 (16)
C7—H7A⋯O1	0.93	2.27	2.8298 (17)	118
C11—H11A⋯O1ii	0.96	2.54	3.3742 (18)	145
C13—H13A⋯O1W	0.96	2.60	3.4997 (18)	157

Symmetry codes: (i) ; (ii) .