Triethyl­ammonium 2,4-dinitro­phenyl­barbiturate

Kalaivani, D.; Malarvizhi, R.

doi:10.1107/S1600536809036976

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2548

doi:10.1107/S1600536809036976

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Triethylammonium 2,4-dinitrophenylbarbiturate

Doraisamyraja Kalaivani ^a ^* and Rangasamy Malarvizhi ^a

^aPG and Research Department of Chemistry, Seethalakshmi Ramaswami College, Tiruchirappalli 620 002, Tamil Nadu, India
^*Correspondence e-mail: kalaivbalaj@yahoo.co.in

(Received 21 August 2009; accepted 12 September 2009; online 26 September 2009)

In the title molecular salt [systematic name: triethylammonium 5-(2,4-dinitrophenyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate], C₆H₁₆N⁺·C₁₀H₅N₄O₇⁻, the cation and anion are linked by an N—H⋯O hydrogen bond. In the crystal, inversion-related barbiturate rings are centrosymmetrically connected through pairs of N—H⋯O hydrogen bonds, forming R₂²(8)R₂²(8) ring motifs.

Related literature

For further information on the anticonvulsant properties of the title compound and general background, see: Kalaivani et al. (2008 ). For a related structure, see: Craven (1964 ). For data on hydrogen-bond motifs in organic crystals, see: Allen et al. (1998 ).

Experimental

Crystal data

C₆H₁₆N⁺·C₁₀H₅N₄O₇⁻
M_r = 395.38
Monoclinic, C 2/c
a = 29.7900 (8) Å
b = 10.4533 (3) Å
c = 11.9606 (3) Å
β = 97.903 (1)°
V = 3689.20 (17) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.942, T_max = 0.971
32882 measured reflections
3217 independent reflections
2493 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.109
S = 1.04
3217 reflections
268 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.84 (2)	2.02 (2)	2.861 (2)	177 (2)
N2—H2⋯O3ⁱⁱ	0.82 (2)	2.10 (2)	2.918 (2)	172 (2)
N5—H5⋯O2	0.85 (2)	1.88 (2)	2.730 (2)	172 (2)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altornare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809036976/hb5061sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809036976/hb5061Isup2.hkl

checkCIF report

Comment top

We have recently prepared the title compound, (I), which has anticonvulsant activity (Kalaivani et al., 2008). We now report its crystal structure.

ORTEP view of the title compound is shown in Fig. 1. The presence of the leaving group (chlorine atom) para with respect to the nitrogroup of the starting molecule (1 – chloro – 2,4 – dinitrobenzene) facilitates the formation of the title compound in the presence of barbituric acid and triethylamine. Absence of chlorine atom, as indicated by the qualitative test on the synthesized barbirutrate has been supported by the crystallographic data. The title molecule is coloured red and it has been attributed to the delocalization of negative charge (Kalaivani et al., 2008) which has also been substantiated by the bond angles and bond lengths of single-crystal X-ray data of 2,4-dinitrophenyl and barbiturate rings. The bond angles and bond lengths of barbiturate residue of the title molecule are compatible with that of barbiturate ion (Craven, 1964), evidencing the delocalization of negative charge in the barbiturate ring.

Presence of double bond (delocalized) between C3 and C5 atoms fixes the configuration of the molecule as depicted in Fig. 1. The N5—H5···O2 hydrogen bond between the asymmetric units is the main driving force for the orientation of the triethylammonium cation (Fig. 2). Two inversion related barbiturate anions interact through a pair of N—H···O=C hydrogen bonds involving N1—H1 atoms and the carbonyl oxygen atom (O1) forming a R₂²(8) ring motif. The same ring motif is also due to a pair of N—H···O hydrogen bonds involving N2—H2 atoms and the carbonyl oxygen atom (O3). This motif is one of the 24 most frequently observed bimolecular cyclic hydrogen-bonded motifs in organic crystal structures (Allen et al., 1998). The hydrogen bonds observed in the title molecule are mainly responsible for its stability. The high solubility of the title drug molecule in water (4 g cc^-1 at 298 K) is due to the positively charged triethylammonium cation and negatively charged 2,4-dinitrophenylbarbiturate anion of the asymmetric unit.

Related literature top

For further information on the anticonvulsant properties of the title compound and general background, see: Kalaivani et al. (2008). For a related structure, see: Craven (1964). For data on hydrogen-bond motifs in organic crystals, see: Allen et al. (1998).

Experimental top

The title compound was prepared as described previously (Kalaivani et al., 2008) and recrystallized from absolute ethanol to yield maroon blocks of (I).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus/XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altornare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) showing 50% displacement ellipsoids.
	Fig. 2. Packing view of (I).

Triethylammonium 5-(2,4-dinitrophenyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate top

Crystal data top

C₆H₁₆N⁺·C₁₀H₅N₄O₇⁻	F(000) = 1664
M_r = 395.38	D_x = 1.424 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8875 reflections
a = 29.7900 (8) Å	θ = 2.5–24.5°
b = 10.4533 (3) Å	µ = 0.11 mm⁻¹
c = 11.9606 (3) Å	T = 293 K
β = 97.903 (1)°	Block, maroon
V = 3689.20 (17) Å³	0.30 × 0.20 × 0.20 mm
Z = 8

Data collection top

Bruker Kappa APEXII CCD diffractometer	3217 independent reflections
Radiation source: fine-focus sealed tube	2493 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω and ϕ scan	θ_max = 24.9°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −35→35
T_min = 0.942, T_max = 0.971	k = −12→12
32882 measured reflections	l = −13→14

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) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0467P)² + 3.5895P] where P = (F_o² + 2F_c²)/3
3217 reflections	(Δ/σ)_max < 0.001
268 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₆H₁₆N⁺·C₁₀H₅N₄O₇⁻	V = 3689.20 (17) Å³
M_r = 395.38	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 29.7900 (8) Å	µ = 0.11 mm⁻¹
b = 10.4533 (3) Å	T = 293 K
c = 11.9606 (3) Å	0.30 × 0.20 × 0.20 mm
β = 97.903 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3217 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	2493 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.971	R_int = 0.036
32882 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.46 e Å⁻³
3217 reflections	Δρ_min = −0.19 e Å⁻³
268 parameters

Special details top

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
C1	0.49607 (6)	0.30537 (17)	0.47768 (17)	0.0402 (5)
C2	0.43235 (6)	0.33505 (16)	0.32947 (15)	0.0336 (4)
C3	0.42904 (6)	0.20117 (16)	0.31524 (15)	0.0339 (4)
C4	0.45876 (6)	0.11860 (16)	0.38266 (15)	0.0348 (4)
C5	0.39223 (6)	0.15178 (15)	0.23248 (14)	0.0321 (4)
C6	0.34717 (6)	0.18925 (16)	0.22995 (14)	0.0317 (4)
C7	0.31314 (6)	0.15443 (17)	0.14568 (15)	0.0372 (4)
H7	0.2835	0.1820	0.1463	0.045*
C8	0.32439 (6)	0.07760 (17)	0.06070 (15)	0.0371 (4)
C9	0.36810 (7)	0.03485 (18)	0.05876 (16)	0.0408 (5)
H9	0.3751	−0.0173	0.0006	0.049*
C10	0.40118 (7)	0.07127 (17)	0.14501 (16)	0.0387 (5)
H10	0.4305	0.0411	0.1449	0.046*
C11	0.39539 (7)	0.7557 (2)	0.27509 (19)	0.0498 (5)
H11A	0.4126	0.7659	0.3495	0.060*
H11B	0.3779	0.8331	0.2577	0.060*
C12	0.42740 (9)	0.7390 (3)	0.1905 (2)	0.0700 (7)
H12A	0.4425	0.6580	0.2022	0.105*
H12B	0.4495	0.8065	0.1991	0.105*
H12C	0.4109	0.7419	0.1158	0.105*
C13	0.33902 (8)	0.6466 (2)	0.37901 (18)	0.0570 (6)
H13A	0.3268	0.7316	0.3877	0.068*
H13B	0.3137	0.5877	0.3659	0.068*
C14	0.36764 (10)	0.6107 (2)	0.48412 (19)	0.0702 (7)
H14A	0.3803	0.5274	0.4757	0.105*
H14B	0.3497	0.6092	0.5448	0.105*
H14C	0.3916	0.6720	0.5006	0.105*
C15	0.33107 (7)	0.6313 (2)	0.17207 (18)	0.0494 (5)
H15A	0.3145	0.5521	0.1768	0.059*
H15B	0.3478	0.6243	0.1083	0.059*
C16	0.29765 (8)	0.7386 (3)	0.1498 (2)	0.0690 (7)
H16A	0.2792	0.7424	0.2096	0.104*
H16B	0.2787	0.7240	0.0793	0.104*
H16C	0.3136	0.8179	0.1464	0.104*
N1	0.46707 (5)	0.37959 (15)	0.40826 (14)	0.0416 (4)
N2	0.49133 (5)	0.17742 (14)	0.46111 (14)	0.0387 (4)
N3	0.33250 (6)	0.26868 (15)	0.31972 (14)	0.0414 (4)
N4	0.28841 (7)	0.04383 (17)	−0.03058 (15)	0.0515 (5)
N5	0.36397 (6)	0.64590 (15)	0.27695 (13)	0.0387 (4)
O1	0.52439 (5)	0.35119 (13)	0.55104 (13)	0.0575 (4)
O2	0.40649 (4)	0.41466 (11)	0.27608 (11)	0.0425 (4)
O3	0.45764 (5)	−0.00016 (12)	0.38115 (12)	0.0496 (4)
O4	0.35005 (6)	0.25162 (15)	0.41664 (12)	0.0582 (4)
O5	0.30234 (5)	0.34649 (15)	0.29215 (14)	0.0582 (4)
O6	0.24947 (6)	0.0672 (2)	−0.01885 (17)	0.0964 (7)
O7	0.29920 (6)	−0.00325 (19)	−0.11540 (15)	0.0808 (6)
H1	0.4688 (7)	0.459 (2)	0.4188 (17)	0.046 (6)*
H2	0.5078 (7)	0.133 (2)	0.5064 (19)	0.050 (6)*
H5	0.3796 (7)	0.577 (2)	0.2791 (17)	0.044 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0371 (10)	0.0255 (9)	0.0527 (12)	−0.0008 (8)	−0.0122 (9)	−0.0017 (8)
C2	0.0337 (10)	0.0252 (9)	0.0386 (10)	0.0012 (7)	−0.0070 (8)	0.0001 (7)
C3	0.0353 (10)	0.0231 (9)	0.0395 (10)	0.0002 (7)	−0.0087 (8)	−0.0012 (7)
C4	0.0373 (10)	0.0231 (9)	0.0408 (10)	0.0002 (7)	−0.0061 (8)	−0.0025 (7)
C5	0.0393 (10)	0.0194 (8)	0.0344 (10)	−0.0015 (7)	−0.0058 (8)	0.0035 (7)
C6	0.0388 (10)	0.0247 (9)	0.0300 (9)	−0.0034 (7)	−0.0005 (8)	0.0003 (7)
C7	0.0349 (10)	0.0353 (10)	0.0394 (11)	−0.0039 (8)	−0.0016 (8)	0.0028 (8)
C8	0.0443 (11)	0.0295 (9)	0.0335 (10)	−0.0057 (8)	−0.0092 (8)	−0.0003 (8)
C9	0.0537 (12)	0.0284 (9)	0.0382 (10)	0.0004 (9)	−0.0019 (9)	−0.0062 (8)
C10	0.0410 (11)	0.0283 (9)	0.0441 (11)	0.0031 (8)	−0.0044 (9)	−0.0032 (8)
C11	0.0497 (13)	0.0374 (11)	0.0579 (13)	−0.0010 (9)	−0.0077 (10)	0.0042 (10)
C12	0.0664 (16)	0.0652 (16)	0.0797 (18)	−0.0033 (13)	0.0145 (14)	0.0200 (14)
C13	0.0710 (15)	0.0484 (13)	0.0549 (14)	0.0046 (11)	0.0203 (12)	−0.0038 (11)
C14	0.107 (2)	0.0575 (15)	0.0484 (14)	0.0062 (14)	0.0207 (14)	0.0066 (11)
C15	0.0528 (13)	0.0432 (12)	0.0495 (12)	−0.0039 (10)	−0.0029 (10)	−0.0025 (10)
C16	0.0522 (14)	0.0725 (17)	0.0766 (17)	0.0098 (12)	−0.0119 (12)	0.0106 (14)
N1	0.0444 (10)	0.0180 (8)	0.0554 (10)	−0.0014 (7)	−0.0185 (8)	−0.0011 (7)
N2	0.0391 (9)	0.0227 (8)	0.0480 (10)	0.0024 (7)	−0.0161 (8)	0.0015 (7)
N3	0.0436 (10)	0.0370 (9)	0.0435 (10)	−0.0082 (8)	0.0053 (8)	−0.0049 (7)
N4	0.0576 (12)	0.0441 (10)	0.0466 (11)	−0.0041 (9)	−0.0151 (9)	−0.0070 (8)
N5	0.0508 (10)	0.0255 (8)	0.0392 (9)	0.0094 (8)	0.0041 (7)	0.0014 (7)
O1	0.0558 (9)	0.0284 (7)	0.0756 (10)	−0.0022 (6)	−0.0366 (8)	−0.0024 (7)
O2	0.0464 (8)	0.0225 (6)	0.0522 (8)	0.0041 (6)	−0.0162 (6)	0.0014 (6)
O3	0.0594 (9)	0.0205 (7)	0.0600 (9)	0.0023 (6)	−0.0234 (7)	−0.0011 (6)
O4	0.0764 (11)	0.0639 (10)	0.0330 (8)	−0.0074 (8)	0.0031 (7)	−0.0084 (7)
O5	0.0499 (9)	0.0512 (9)	0.0730 (11)	0.0085 (8)	0.0067 (8)	−0.0125 (8)
O6	0.0495 (11)	0.150 (2)	0.0822 (14)	−0.0072 (12)	−0.0177 (10)	−0.0414 (13)
O7	0.0883 (13)	0.0883 (14)	0.0564 (11)	0.0148 (11)	−0.0234 (9)	−0.0350 (10)

Geometric parameters (Å, º) top

C1—O1	1.228 (2)	C12—H12A	0.9600
C1—N2	1.357 (2)	C12—H12B	0.9600
C1—N1	1.357 (2)	C12—H12C	0.9600
C2—O2	1.248 (2)	C13—C14	1.467 (3)
C2—N1	1.381 (2)	C13—N5	1.514 (3)
C2—C3	1.412 (2)	C13—H13A	0.9700
C3—C4	1.408 (2)	C13—H13B	0.9700
C3—C5	1.466 (2)	C14—H14A	0.9600
C4—O3	1.242 (2)	C14—H14B	0.9600
C4—N2	1.396 (2)	C14—H14C	0.9600
C5—C6	1.395 (2)	C15—N5	1.490 (2)
C5—C10	1.397 (3)	C15—C16	1.498 (3)
C6—C7	1.377 (2)	C15—H15A	0.9700
C6—N3	1.471 (2)	C15—H15B	0.9700
C7—C8	1.373 (3)	C16—H16A	0.9600
C7—H7	0.9300	C16—H16B	0.9600
C8—C9	1.380 (3)	C16—H16C	0.9600
C8—N4	1.464 (2)	N1—H1	0.84 (2)
C9—C10	1.379 (3)	N2—H2	0.82 (2)
C9—H9	0.9300	N3—O4	1.217 (2)
C10—H10	0.9300	N3—O5	1.223 (2)
C11—N5	1.483 (3)	N4—O7	1.210 (2)
C11—C12	1.492 (3)	N4—O6	1.212 (2)
C11—H11A	0.9700	N5—H5	0.85 (2)
C11—H11B	0.9700

O1—C1—N2	122.44 (17)	C14—C13—N5	113.4 (2)
O1—C1—N1	122.11 (17)	C14—C13—H13A	108.9
N2—C1—N1	115.45 (16)	N5—C13—H13A	108.9
O2—C2—N1	118.42 (15)	C14—C13—H13B	108.9
O2—C2—C3	124.84 (16)	N5—C13—H13B	108.9
N1—C2—C3	116.74 (15)	H13A—C13—H13B	107.7
C4—C3—C2	120.71 (16)	C13—C14—H14A	109.5
C4—C3—C5	121.58 (15)	C13—C14—H14B	109.5
C2—C3—C5	117.63 (15)	H14A—C14—H14B	109.5
O3—C4—N2	117.69 (16)	C13—C14—H14C	109.5
O3—C4—C3	126.22 (16)	H14A—C14—H14C	109.5
N2—C4—C3	116.04 (15)	H14B—C14—H14C	109.5
C6—C5—C10	115.80 (16)	N5—C15—C16	114.65 (18)
C6—C5—C3	122.95 (16)	N5—C15—H15A	108.6
C10—C5—C3	121.05 (17)	C16—C15—H15A	108.6
C7—C6—C5	123.46 (16)	N5—C15—H15B	108.6
C7—C6—N3	114.89 (16)	C16—C15—H15B	108.6
C5—C6—N3	121.64 (15)	H15A—C15—H15B	107.6
C8—C7—C6	117.81 (17)	C15—C16—H16A	109.5
C8—C7—H7	121.1	C15—C16—H16B	109.5
C6—C7—H7	121.1	H16A—C16—H16B	109.5
C7—C8—C9	121.94 (16)	C15—C16—H16C	109.5
C7—C8—N4	117.70 (18)	H16A—C16—H16C	109.5
C9—C8—N4	120.34 (17)	H16B—C16—H16C	109.5
C10—C9—C8	118.50 (17)	C1—N1—C2	125.39 (16)
C10—C9—H9	120.8	C1—N1—H1	116.9 (14)
C8—C9—H9	120.8	C2—N1—H1	117.4 (14)
C9—C10—C5	122.44 (18)	C1—N2—C4	125.53 (16)
C9—C10—H10	118.8	C1—N2—H2	114.8 (16)
C5—C10—H10	118.8	C4—N2—H2	119.4 (16)
N5—C11—C12	112.55 (18)	O4—N3—O5	123.88 (17)
N5—C11—H11A	109.1	O4—N3—C6	118.73 (16)
C12—C11—H11A	109.1	O5—N3—C6	117.36 (16)
N5—C11—H11B	109.1	O7—N4—O6	123.20 (18)
C12—C11—H11B	109.1	O7—N4—C8	118.14 (19)
H11A—C11—H11B	107.8	O6—N4—C8	118.64 (19)
C11—C12—H12A	109.5	C11—N5—C15	114.20 (16)
C11—C12—H12B	109.5	C11—N5—C13	112.90 (17)
H12A—C12—H12B	109.5	C15—N5—C13	109.90 (17)
C11—C12—H12C	109.5	C11—N5—H5	107.9 (14)
H12A—C12—H12C	109.5	C15—N5—H5	103.4 (14)
H12B—C12—H12C	109.5	C13—N5—H5	107.9 (14)

O2—C2—C3—C4	−177.48 (19)	C3—C5—C10—C9	−172.52 (17)
N1—C2—C3—C4	2.8 (3)	O1—C1—N1—C2	−175.1 (2)
O2—C2—C3—C5	−0.7 (3)	N2—C1—N1—C2	4.3 (3)
N1—C2—C3—C5	179.64 (17)	O2—C2—N1—C1	175.63 (19)
C2—C3—C4—O3	176.4 (2)	C3—C2—N1—C1	−4.7 (3)
C5—C3—C4—O3	−0.2 (3)	O1—C1—N2—C4	177.2 (2)
C2—C3—C4—N2	−1.0 (3)	N1—C1—N2—C4	−2.2 (3)
C5—C3—C4—N2	−177.72 (17)	O3—C4—N2—C1	−177.0 (2)
C4—C3—C5—C6	126.7 (2)	C3—C4—N2—C1	0.7 (3)
C2—C3—C5—C6	−50.1 (3)	C7—C6—N3—O4	142.69 (17)
C4—C3—C5—C10	−58.6 (3)	C5—C6—N3—O4	−36.5 (2)
C2—C3—C5—C10	124.63 (19)	C7—C6—N3—O5	−35.6 (2)
C10—C5—C6—C7	−2.2 (3)	C5—C6—N3—O5	145.17 (17)
C3—C5—C6—C7	172.76 (17)	C7—C8—N4—O7	166.62 (19)
C10—C5—C6—N3	176.93 (15)	C9—C8—N4—O7	−12.1 (3)
C3—C5—C6—N3	−8.1 (3)	C7—C8—N4—O6	−11.6 (3)
C5—C6—C7—C8	0.7 (3)	C9—C8—N4—O6	169.7 (2)
N3—C6—C7—C8	−178.44 (16)	C12—C11—N5—C15	−66.8 (2)
C6—C7—C8—C9	0.5 (3)	C12—C11—N5—C13	166.72 (18)
C6—C7—C8—N4	−178.22 (16)	C16—C15—N5—C11	−65.2 (3)
C7—C8—C9—C10	−0.2 (3)	C16—C15—N5—C13	62.8 (2)
N4—C8—C9—C10	178.53 (17)	C14—C13—N5—C11	−73.7 (2)
C8—C9—C10—C5	−1.4 (3)	C14—C13—N5—C15	157.55 (19)
C6—C5—C10—C9	2.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.84 (2)	2.02 (2)	2.861 (2)	177 (2)
N2—H2···O3ⁱⁱ	0.82 (2)	2.10 (2)	2.918 (2)	172 (2)
N5—H5···O2	0.85 (2)	1.88 (2)	2.730 (2)	172 (2)

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

Experimental details

Crystal data
Chemical formula	C₆H₁₆N⁺·C₁₀H₅N₄O₇⁻
M_r	395.38
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	29.7900 (8), 10.4533 (3), 11.9606 (3)
β (°)	97.903 (1)
V (Å³)	3689.20 (17)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.942, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	32882, 3217, 2493
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.593

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.109, 1.04
No. of reflections	3217
No. of parameters	268
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.19

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SAINT-Plus/XPREP (Bruker, 2004), SIR92 (Altornare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.84 (2)	2.02 (2)	2.861 (2)	177 (2)
N2—H2···O3ⁱⁱ	0.82 (2)	2.10 (2)	2.918 (2)	172 (2)
N5—H5···O2	0.85 (2)	1.88 (2)	2.730 (2)	172 (2)

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

Acknowledgements

The authors are thankful to SAIF, IIT Madras, for the crystal data.

References

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