2,3-Diamino­pyridinium 4-meth­oxy­quinoline-2-carboxyl­ate

Thanigaimani, K.; Khalib, N.C.; Arshad, S.; Razak, I.A.

doi:10.1107/S1600536812047642

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages o3444-o3445

doi:10.1107/S1600536812047642

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2,3-Diaminopyridinium 4-methoxyquinoline-2-carboxylate

Kaliyaperumal Thanigaimani,^a Nuridayanti Che Khalib,^a Suhana Arshad ^a and Ibrahim Abdul Razak ^a ^*‡

^aSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: arazaki@usm.my

(Received 5 November 2012; accepted 20 November 2012; online 24 November 2012)

In the 4-methoxyquinoline-2-carboxylate anion of the title salt, C₅H₈N₃⁺·C₁₁H₈NO₃⁻, the dihedral angle between the quinoline ring system and the carboxylate group is 16.54 (15)°. In the crystal, the cations and anions are linked via N—H⋯O and N—H⋯N hydrogen bonds, forming a centrosymmetric 2 + 2 aggregate with R₂²(9) and R₄²(8) ring motifs. These units are further connected via N—H⋯O hydrogen bonds into a layer parallel to the bc plane. The crystal structure is also stabilized by weak C—H⋯O hydrogen bonds and π–π interactions between pyridine rings [centroid–centroid distance = 3.5886 (8) Å] and between pyridine and benzene rings [centroid–centroid distance = 3.6328 (8) Å].

Related literature

For background to the chemistry of substituted pyridines, see: Pozharski et al. (1997 ); Katritzky et al. (1996 ). For background to and the biological activity of quinoline derivatives, see: Morimoto et al. (1991 ); Markees et al. (1970 ). For a related structure, see: Hemamalini & Fun (2011 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₅H₈N₃⁺·C₁₁H₈NO₃⁻
M_r = 312.33
Monoclinic, P 2₁ /c
a = 12.4338 (12) Å
b = 7.7462 (7) Å
c = 19.4626 (14) Å
β = 128.806 (4)°
V = 1460.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.24 × 0.21 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.976, T_max = 0.989
17919 measured reflections
4820 independent reflections
3806 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.131
S = 1.02
4820 reflections
229 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H2⋯O3	0.91 (2)	1.890 (19)	2.7670 (18)	162.8 (19)
N2—H3⋯N1	0.94 (2)	1.94 (3)	2.843 (2)	162.5 (19)
N3—H1⋯O3ⁱ	0.89 (2)	1.94 (2)	2.812 (2)	163.4 (16)
N4—H4⋯O2ⁱⁱ	0.893 (18)	1.978 (19)	2.8617 (15)	169.8 (17)
N4—H5⋯O2ⁱ	0.88 (2)	2.17 (3)	2.9419 (18)	146 (3)
C4—H4A⋯O2ⁱⁱⁱ	0.95	2.45	3.3529 (15)	158
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812047642/is5215sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812047642/is5215Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812047642/is5215Isup3.cml

checkCIF report

Comment top

Pyridine and its derivatives play an important role in heterocyclic chemistry (Pozharski et al., 1997; Katritzky et al., 1996). Quinolines and their derivatives are very important compounds because of their wide occurrence in natural products (Morimoto et al., 1991) and biologically active compounds (Markees et al., 1970). Recently, hydrogen-bonding patterns involving 4-methoxyquinolinium-2-carboxylate dihydrate (Hemamalini & Fun, 2011) have been reported. In order to study some interesting hydrogen bonding interactions, the synthesis and structure of the title compound, (I), is presented here.

The asymmetric unit (Fig. 1) contains one 2,3-diaminopyridinium cation and one 4-methoxyquinoline-2-carboxylate anion. In the 2,3-diaminopyridinium cation, the protonated N2 atom has lead to a slight increase in the C12—N2—C16 angle to 123.67 (14)°. The 2,3-diaminopyridinium cation is planar, with a maximum deviation of 0.005 (1) Å for atom C14. The bond lengths (Allen et al., 1987) and angles are normal.

In the crystal packing (Fig. 2), the 2-amino groups (N3 and N4) are hydrogen bonded to the carboxylate oxygen atoms (O3 and O2) via a pair of intermolecular N3—H1···O3ⁱ and N4—H5···O2ⁱ hydrogen bonds (symmetry code in Table 1), forming an R₂²(9) (Bernstein et al., 1995) ring motif. These motifs are crosslinked via N3—H2···O3 and N2—H3···N1 hydrogen bonds to produce a DDAA array (where D is a hydrogen-bond donor and A is a hydrogen-bond acceptor) with R₂²(9) and R₄²(8) motifs. The crystal structure also features weak N4—H4···O2ⁱⁱ and C4—H4A···O2ⁱⁱⁱ hydrogen bonds (symmetry codes in Table 1). Furthermore, the crystal structure is stabilized by the following π–π interactions: (a) between pyridine rings (N2/C12–C16, centroid Cg4) Cg4···Cg4 (1 - x, 1 - y, 1 - z) 3.5886 (8) Å and (b) between pyridine (N1/C1/C6–C9, centroid Cg1) and benzene (C1–C6, centroid Cg2) rings Cg1···Cg2 (2 - x, 1 - y, 1 - z) 3.6328 (8) Å.

Related literature top

For background to the chemistry of substituted pyridines, see: Pozharski et al. (1997); Katritzky et al. (1996). For background to and the biological activity of quinoline derivatives, see: Morimoto et al. (1991); Markees et al. (1970). For a related structure, see: Hemamalini & Fun (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

Hot methanol solutions (20 ml) of 2,3-diaminopyrimidine (27 mg, Aldrich) and 4-Methoxy-2-quinolinecarboxylic acid (50 mg, Merck) were mixed and warmed over a heating magnetic stirrer hotplate for a few minutes. The resulting solution was allowed to cool slowly at room temperature and crystals of the title compound (I) appeared after a few days.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with atom labels with 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound. The H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

2,3-Diaminopyridinium 4-methoxyquinoline-2-carboxylate top

Crystal data top

C₅H₈N₃⁺·C₁₁H₈NO₃⁻	F(000) = 656
M_r = 312.33	D_x = 1.420 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4575 reflections
a = 12.4338 (12) Å	θ = 2.7–31.3°
b = 7.7462 (7) Å	µ = 0.10 mm⁻¹
c = 19.4626 (14) Å	T = 100 K
β = 128.806 (4)°	Block, brown
V = 1460.8 (2) Å³	0.24 × 0.21 × 0.11 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4820 independent reflections
Radiation source: fine-focus sealed tube	3806 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 31.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −18→18
T_min = 0.976, T_max = 0.989	k = −11→11
17919 measured reflections	l = −28→28

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0667P)² + 0.4735P] where P = (F_o² + 2F_c²)/3
4820 reflections	(Δ/σ)_max < 0.001
229 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₅H₈N₃⁺·C₁₁H₈NO₃⁻	V = 1460.8 (2) Å³
M_r = 312.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.4338 (12) Å	µ = 0.10 mm⁻¹
b = 7.7462 (7) Å	T = 100 K
c = 19.4626 (14) Å	0.24 × 0.21 × 0.11 mm
β = 128.806 (4)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4820 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3806 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.989	R_int = 0.036
17919 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.54 e Å⁻³
4820 reflections	Δρ_min = −0.24 e Å⁻³
229 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

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

	x	y	z	U_iso*/U_eq
O1	1.05026 (9)	0.82361 (12)	0.41897 (6)	0.02018 (19)
O2	0.57301 (9)	0.98701 (12)	0.31851 (6)	0.02111 (19)
O3	0.59315 (10)	0.93999 (14)	0.43875 (7)	0.0273 (2)
N1	0.82921 (10)	0.75610 (13)	0.51232 (6)	0.0165 (2)
C1	0.96096 (11)	0.69323 (14)	0.55691 (7)	0.0157 (2)
C2	1.02304 (12)	0.60542 (16)	0.63772 (8)	0.0195 (2)
H2A	0.9720	0.5869	0.6583	0.023*
C3	1.15663 (13)	0.54699 (16)	0.68650 (8)	0.0214 (2)
H3A	1.1969	0.4874	0.7403	0.026*
C4	1.23432 (12)	0.57458 (16)	0.65750 (8)	0.0222 (2)
H4A	1.3269	0.5347	0.6921	0.027*
C5	1.17713 (12)	0.65876 (16)	0.57956 (8)	0.0193 (2)
H5A	1.2303	0.6772	0.5605	0.023*
C6	1.03897 (11)	0.71840 (15)	0.52728 (7)	0.0159 (2)
C7	0.97352 (11)	0.80680 (15)	0.44581 (8)	0.0156 (2)
C8	0.84151 (11)	0.87022 (15)	0.40172 (7)	0.0156 (2)
H8A	0.7961	0.9300	0.3474	0.019*
C9	0.77543 (11)	0.84423 (15)	0.43910 (7)	0.0151 (2)
C10	0.63500 (12)	0.92902 (15)	0.39471 (8)	0.0167 (2)
C11	0.98637 (14)	0.90182 (19)	0.33460 (9)	0.0239 (3)
H11A	1.0535	0.9092	0.3239	0.036*
H11B	0.9545	1.0180	0.3339	0.036*
H11C	0.9075	0.8316	0.2884	0.036*
N2	0.69022 (11)	0.60036 (14)	0.56941 (7)	0.0186 (2)
N3	0.61802 (11)	0.86007 (14)	0.58672 (7)	0.0187 (2)
N4	0.53416 (12)	0.68143 (16)	0.67353 (8)	0.0242 (2)
C12	0.63244 (11)	0.68819 (15)	0.59866 (7)	0.0156 (2)
C13	0.59474 (11)	0.59571 (16)	0.64456 (7)	0.0169 (2)
C14	0.62055 (13)	0.41992 (16)	0.65640 (8)	0.0205 (2)
H14A	0.5978	0.3557	0.6873	0.025*
C15	0.67973 (13)	0.33474 (17)	0.62363 (9)	0.0230 (3)
H15A	0.6954	0.2138	0.6316	0.028*
C16	0.71448 (13)	0.42631 (16)	0.58045 (8)	0.0222 (2)
H16A	0.7550	0.3702	0.5583	0.027*
H1	0.5578 (18)	0.916 (2)	0.5893 (11)	0.026 (4)*
H2	0.6256 (18)	0.899 (2)	0.5461 (11)	0.025 (4)*
H3	0.7185 (18)	0.663 (2)	0.5421 (12)	0.032 (5)*
H4	0.5352 (19)	0.630 (2)	0.7151 (12)	0.032 (5)*
H5	0.525 (2)	0.795 (3)	0.6708 (13)	0.041 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0191 (4)	0.0250 (4)	0.0228 (4)	0.0005 (3)	0.0162 (4)	0.0014 (3)
O2	0.0206 (4)	0.0255 (5)	0.0171 (4)	0.0057 (3)	0.0118 (3)	0.0008 (3)
O3	0.0298 (5)	0.0345 (5)	0.0303 (5)	0.0146 (4)	0.0251 (4)	0.0128 (4)
N1	0.0184 (4)	0.0158 (4)	0.0181 (4)	0.0026 (3)	0.0128 (4)	0.0007 (3)
C1	0.0179 (5)	0.0139 (5)	0.0172 (5)	0.0012 (4)	0.0119 (4)	−0.0007 (4)
C2	0.0222 (5)	0.0188 (5)	0.0184 (5)	0.0021 (4)	0.0132 (5)	0.0010 (4)
C3	0.0217 (5)	0.0193 (6)	0.0169 (5)	0.0013 (4)	0.0090 (4)	0.0009 (4)
C4	0.0161 (5)	0.0196 (6)	0.0229 (6)	0.0010 (4)	0.0083 (5)	−0.0010 (4)
C5	0.0158 (5)	0.0183 (5)	0.0226 (6)	−0.0006 (4)	0.0114 (4)	−0.0026 (4)
C6	0.0159 (5)	0.0139 (5)	0.0180 (5)	−0.0003 (4)	0.0107 (4)	−0.0024 (4)
C7	0.0167 (5)	0.0151 (5)	0.0189 (5)	−0.0021 (4)	0.0130 (4)	−0.0028 (4)
C8	0.0174 (5)	0.0151 (5)	0.0165 (5)	0.0003 (4)	0.0117 (4)	−0.0007 (4)
C9	0.0171 (5)	0.0142 (5)	0.0165 (5)	0.0013 (4)	0.0117 (4)	−0.0009 (4)
C10	0.0182 (5)	0.0155 (5)	0.0197 (5)	0.0020 (4)	0.0136 (4)	0.0005 (4)
C11	0.0258 (6)	0.0296 (7)	0.0236 (6)	0.0015 (5)	0.0191 (5)	0.0027 (5)
N2	0.0216 (5)	0.0197 (5)	0.0207 (5)	0.0027 (4)	0.0162 (4)	0.0017 (4)
N3	0.0231 (5)	0.0176 (5)	0.0226 (5)	0.0035 (4)	0.0178 (4)	0.0037 (4)
N4	0.0329 (6)	0.0248 (6)	0.0300 (6)	0.0098 (4)	0.0271 (5)	0.0095 (4)
C12	0.0149 (4)	0.0183 (5)	0.0146 (5)	0.0021 (4)	0.0097 (4)	0.0010 (4)
C13	0.0158 (5)	0.0205 (5)	0.0159 (5)	0.0015 (4)	0.0107 (4)	0.0023 (4)
C14	0.0218 (5)	0.0195 (5)	0.0231 (6)	0.0013 (4)	0.0154 (5)	0.0038 (4)
C15	0.0254 (6)	0.0174 (5)	0.0260 (6)	0.0029 (4)	0.0160 (5)	0.0017 (5)
C16	0.0263 (6)	0.0197 (6)	0.0237 (6)	0.0049 (4)	0.0172 (5)	0.0004 (5)

Geometric parameters (Å, º) top

O1—C7	1.3509 (13)	C9—C10	1.5284 (15)
O1—C11	1.4351 (15)	C11—H11A	0.9800
O2—C10	1.2501 (14)	C11—H11B	0.9800
O3—C10	1.2537 (14)	C11—H11C	0.9800
N1—C9	1.3227 (15)	N2—C12	1.3475 (15)
N1—C1	1.3755 (14)	N2—C16	1.3688 (16)
C1—C2	1.4179 (16)	N2—H3	0.936 (18)
C1—C6	1.4185 (16)	N3—C12	1.3441 (15)
C2—C3	1.3743 (17)	N3—H1	0.893 (18)
C2—H2A	0.9500	N3—H2	0.905 (17)
C3—C4	1.4073 (19)	N4—C13	1.3634 (16)
C3—H3A	0.9500	N4—H4	0.893 (18)
C4—C5	1.3712 (18)	N4—H5	0.88 (2)
C4—H4A	0.9500	C12—C13	1.4337 (16)
C5—C6	1.4174 (15)	C13—C14	1.3848 (17)
C5—H5A	0.9500	C14—C15	1.4041 (18)
C6—C7	1.4242 (16)	C14—H14A	0.9500
C7—C8	1.3808 (15)	C15—C16	1.3606 (19)
C8—C9	1.4121 (16)	C15—H15A	0.9500
C8—H8A	0.9500	C16—H16A	0.9500

C7—O1—C11	117.67 (9)	O3—C10—C9	117.34 (10)
C9—N1—C1	117.42 (10)	O1—C11—H11A	109.5
N1—C1—C2	118.35 (10)	O1—C11—H11B	109.5
N1—C1—C6	122.84 (10)	H11A—C11—H11B	109.5
C2—C1—C6	118.76 (10)	O1—C11—H11C	109.5
C3—C2—C1	120.42 (11)	H11A—C11—H11C	109.5
C3—C2—H2A	119.8	H11B—C11—H11C	109.5
C1—C2—H2A	119.8	C12—N2—C16	123.66 (11)
C2—C3—C4	120.61 (11)	C12—N2—H3	117.9 (11)
C2—C3—H3A	119.7	C16—N2—H3	118.4 (11)
C4—C3—H3A	119.7	C12—N3—H1	119.7 (11)
C5—C4—C3	120.36 (11)	C12—N3—H2	113.9 (11)
C5—C4—H4A	119.8	H1—N3—H2	116.0 (16)
C3—C4—H4A	119.8	C13—N4—H4	117.5 (12)
C4—C5—C6	120.27 (11)	C13—N4—H5	122.8 (13)
C4—C5—H5A	119.9	H4—N4—H5	115.1 (17)
C6—C5—H5A	119.9	N3—C12—N2	118.40 (11)
C5—C6—C1	119.56 (11)	N3—C12—C13	122.85 (11)
C5—C6—C7	123.07 (11)	N2—C12—C13	118.68 (11)
C1—C6—C7	117.36 (10)	N4—C13—C14	122.73 (11)
O1—C7—C8	125.32 (11)	N4—C13—C12	119.69 (11)
O1—C7—C6	115.32 (10)	C14—C13—C12	117.57 (11)
C8—C7—C6	119.35 (10)	C13—C14—C15	121.28 (11)
C7—C8—C9	118.56 (10)	C13—C14—H14A	119.4
C7—C8—H8A	120.7	C15—C14—H14A	119.4
C9—C8—H8A	120.7	C16—C15—C14	119.68 (12)
N1—C9—C8	124.34 (10)	C16—C15—H15A	120.2
N1—C9—C10	117.26 (10)	C14—C15—H15A	120.2
C8—C9—C10	118.36 (10)	C15—C16—N2	119.11 (11)
O2—C10—O3	125.12 (11)	C15—C16—H16A	120.4
O2—C10—C9	117.50 (10)	N2—C16—H16A	120.4

C9—N1—C1—C2	177.07 (11)	C6—C7—C8—C9	−0.28 (16)
C9—N1—C1—C6	−0.38 (16)	C1—N1—C9—C8	3.32 (17)
N1—C1—C2—C3	−177.15 (11)	C1—N1—C9—C10	−174.09 (10)
C6—C1—C2—C3	0.41 (18)	C7—C8—C9—N1	−3.03 (18)
C1—C2—C3—C4	0.56 (19)	C7—C8—C9—C10	174.35 (10)
C2—C3—C4—C5	−0.68 (19)	N1—C9—C10—O2	−168.15 (11)
C3—C4—C5—C6	−0.19 (19)	C8—C9—C10—O2	14.27 (16)
C4—C5—C6—C1	1.15 (17)	N1—C9—C10—O3	14.14 (16)
C4—C5—C6—C7	179.93 (11)	C8—C9—C10—O3	−163.43 (11)
N1—C1—C6—C5	176.19 (11)	C16—N2—C12—N3	177.71 (11)
C2—C1—C6—C5	−1.25 (17)	C16—N2—C12—C13	0.46 (17)
N1—C1—C6—C7	−2.65 (16)	N3—C12—C13—N4	3.90 (17)
C2—C1—C6—C7	179.90 (11)	N2—C12—C13—N4	−178.98 (11)
C11—O1—C7—C8	−5.09 (17)	N3—C12—C13—C14	−176.96 (11)
C11—O1—C7—C6	176.10 (10)	N2—C12—C13—C14	0.16 (16)
C5—C6—C7—O1	2.97 (16)	N4—C13—C14—C15	178.25 (12)
C1—C6—C7—O1	−178.23 (10)	C12—C13—C14—C15	−0.86 (18)
C5—C6—C7—C8	−175.92 (11)	C13—C14—C15—C16	0.96 (19)
C1—C6—C7—C8	2.88 (16)	C14—C15—C16—N2	−0.34 (19)
O1—C7—C8—C9	−179.05 (11)	C12—N2—C16—C15	−0.37 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H2···O3	0.91 (2)	1.890 (19)	2.7670 (18)	162.8 (19)
N2—H3···N1	0.94 (2)	1.94 (3)	2.843 (2)	162.5 (19)
N3—H1···O3ⁱ	0.89 (2)	1.94 (2)	2.812 (2)	163.4 (16)
N4—H4···O2ⁱⁱ	0.893 (18)	1.978 (19)	2.8617 (15)	169.8 (17)
N4—H5···O2ⁱ	0.88 (2)	2.17 (3)	2.9419 (18)	146 (3)
C4—H4A···O2ⁱⁱⁱ	0.95	2.45	3.3529 (15)	158

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x, −y+3/2, z+1/2; (iii) x+1, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₅H₈N₃⁺·C₁₁H₈NO₃⁻
M_r	312.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	12.4338 (12), 7.7462 (7), 19.4626 (14)
β (°)	128.806 (4)
V (Å³)	1460.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.24 × 0.21 × 0.11

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.976, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	17919, 4820, 3806
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.734

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.131, 1.02
No. of reflections	4820
No. of parameters	229
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.24

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H2···O3	0.91 (2)	1.890 (19)	2.7670 (18)	162.8 (19)
N2—H3···N1	0.94 (2)	1.94 (3)	2.843 (2)	162.5 (19)
N3—H1···O3ⁱ	0.89 (2)	1.94 (2)	2.812 (2)	163.4 (16)
N4—H4···O2ⁱⁱ	0.893 (18)	1.978 (19)	2.8617 (15)	169.8 (17)
N4—H5···O2ⁱ	0.88 (2)	2.17 (3)	2.9419 (18)	146 (3)
C4—H4A···O2ⁱⁱⁱ	0.95	2.45	3.3529 (15)	158

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x, −y+3/2, z+1/2; (iii) x+1, −y+3/2, z+1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the research facilities and Fundamental Research Grant Scheme (FRGS) No. 203/PFIZIK/6711171 to conduct this work. KT thanks The Academy of Sciences for the Developing World and USM for a TWAS–USM fellowship.

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