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

Fun, H.-K.; Kia, R.; Das, N.K.; Sen, D.; Goswami, S.

doi:10.1107/S1600536808042955

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o340

doi:10.1107/S1600536808042955

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

Hoong-Kun Fun,^a ^* Reza Kia,^a Nirmal Kumar Das,^b Debabrata Sen ^b and Shyamaprosad Goswami ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Bengal Engineering and Science University, Shibpur, Howrah 711 103, India
^*Correspondence e-mail: hkfun@usm.my

(Received 15 December 2008; accepted 17 December 2008; online 17 January 2009)

The asymmetric unit of the title compound, C₁₄H₁₈N₃O⁺·Cl⁻·H₂O, comprises a substituted amido–naphthyridine cation, a chloride anion and a water molecule of crystallization. Intramolecular 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 intermolecular N—H⋯O, N—H⋯Cl, O—H⋯Cl (× 2), and C—H⋯O (× 2) hydrogen bonds. These interactions linked neighbouring molecules into chains along the a and b axes of the crystal, thus forming molecular 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_r = 297.78
Orthorhombic, P b c n
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 (SADABS; 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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.102
S = 1.07
4489 reflections
198 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.27 e Å⁻³

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) -x+1, -y, -z+2; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

Naphthyridine or naphthyridone systems are of great importance due to their broad spectrum of biological activities. Substituted 1,8-naphthyridine compounds are used as antihypertensives, antiarrhythmics, herbicide safeners and also as immunostimulants (Goswami et al., 2005). Naphthyridine molecules also have interesting crystal structures (Carmen et al., 2004) and are used in molecular recognition chemistry (Goswami et al., 2005; Yu et al., 2008).

In the title compound (I), Fig. 1, intramolecular C—H···O hydrogen bond generates six-membered ring, producing S(6) ring motif (Bernstein et al., 1995). The chloride anion and water molecule are mediated to link neighbouring molecules together through hydrogen bonds. The amido group is twisted from the naphthyridine ring making a dihedral angle of 17.65 (7)°. The crystal structure is stabilized by intermolecular N—H···O, N—H···Cl, O—H···Cl(x 2), and C—H···O (x 2) hydrogen bonds. These interactions linked neighbouring molecules together as chains along the a and b axes of the crystal, thus forming 2-D molecular sheets parallel to the (001) plane.

Related literature top

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 top

In a round bottom flask, 7-methyl-[1,8]naphthyridin-2-ylamine (100 mg, 0.63 mmol) and triethyl amine (0.1 mL) were stirred in dry dichloromethane (1 mL) under nitrogen at 0 ^° C. Pivaloyl chloride (0.116 mL, 0.95 mmol) was then added dropwise. After 1 h, the solvent was removed and the residue was neutralized with saturated NaHCO₃ and fresh dichloromethane was added. The organic part was collected and removed under reduced pressure. The crude product was then purified by column chromatography using ethylacetate and petroleum ether (1:1) which offered the entitled compound as an off-white crystalline solid (82 mg, 53%), m.p. 66-68 ^° C.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005)'; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atomic numbering. Dashed line show intramolecular hydrogen bond.
	Fig. 2. The crystal packing for (I), viewed down the b-axis showing linking of molecules along the a-axis. Intermolecular interactions are drawn as dashed lines.

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

Crystal data top

C₁₄H₁₈N₃O⁺·Cl⁻·H₂O	F(000) = 1264
M_r = 297.78	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0453P)² + 0.653P] where P = (F_o² + 2F_c²)/3
4489 reflections	(Δ/σ)_max = 0.001
198 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₄H₁₈N₃O⁺·Cl⁻·H₂O	V = 3035.79 (14) Å³
M_r = 297.78	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 19.0092 (5) Å	µ = 0.26 mm⁻¹
b = 9.0077 (2) Å	T = 100 K
c = 17.7294 (5) Å	0.41 × 0.29 × 0.19 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4489 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3470 reflections with I > 2σ(I)
T_min = 0.902, T_max = 0.954	R_int = 0.037
19927 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.36 e Å⁻³
4489 reflections	Δρ_min = −0.27 e Å⁻³
198 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+2; (ii) −x+1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₈N₃O⁺·Cl⁻·H₂O
M_r	297.78
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	100
a, b, c (Å)	19.0092 (5), 9.0077 (2), 17.7294 (5)
V (Å³)	3035.79 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.41 × 0.29 × 0.19

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.902, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	19927, 4489, 3470
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.708

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.102, 1.07
No. of reflections	4489
No. of parameters	198
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.27

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005)', SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

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	0.9300	2.2700	2.8298 (17)	118.00
C11—H11A···O1ⁱⁱ	0.9600	2.5400	3.3742 (18)	145.00
C13—H13A···O1W	0.9600	2.6000	3.4997 (18)	157.00

Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+1/2, y−1/2, z.

Acknowledgements

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. We thank the DST [SR /S1/OC-13/2005], Government of India, for financial support. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chamg, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Carmen, A.-R., Garcia-Granda, S., Goswami, S., Mukherjee, R., Dey, S., Claramunt, R. M., Santa Maria, M. D., Rozas, I., Jagerovic, N., Alkorta, I. & Elguero, J. (2004). New J. Chem. 28, 700–705. Google Scholar
Goswami, S. & Mukherjee, R. (1997). Tetrahedron Lett. 38, 1619–1621. CrossRef CAS Web of Science Google Scholar
Goswami, S., Mukherjee, R., Mukherjee, S., Jana, S., Maity, A. C. & Adak, A. K. (2005). Molecules, 10, 929–934. Web of Science CrossRef PubMed CAS Google Scholar
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Volume 65| Part 2| February 2009| Page o340

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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