Triethyl­ammonium 1,3-dimethyl-5-(2,4,6-trinitro­phenyl)barbiturate

Rajamani, K.; Kalaivani, D.

doi:10.1107/S1600536812030450

organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2395

https://doi.org/10.1107/S1600536812030450

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Triethylammonium 1,3-dimethyl-5-(2,4,6-trinitrophenyl)barbiturate

Kulandaiya Rajamani ^a and Doraisamyraja Kalaivani ^a ^*

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

(Received 1 July 2012; accepted 4 July 2012; online 10 July 2012)

In the title molecular salt [systematic name: triethylammonium 1,3-dimethyl-2,6-dioxo-5-(2,4,6-trinitrophenyl)-1,2,3,6-tetrahydropyrimidin-4-olate], C₆H₁₆N⁺·C₁₂H₈N₅O₉⁻, the dihedral angle between the aromatic rings in the anion is 46.88 (8)°. The nitro group para to the ring junction is almost coplanar with its attached ring [dihedral angle = 0.76 (3)°], but the two ortho-nitro groups are substantially twisted from the ring plane, by 47.91 (2) and 42.90 (1)°. In the crystal, the cation and anion are linked by an N—H⋯O=C hydrogen bond; these dimeric associations are further connected by weak C—H⋯O bonds to form linear supramolecular chains extending in the [001] direction.

Related literature

For background to barbiturates, see: Tripathi (2009 ). For our recent work in this area, see: Kalaivani & Buvaneswari, 2010 ); Kalaivani & Malarvizhi (2009 ); Buvaneswari & Kalaivani (2011 ); Babykala & Kalaivani (2012 ).

Experimental

Crystal data

C₆H₁₆N⁺·C₁₂H₈N₅O₉⁻
M_r = 468.43
Monoclinic, P 2₁ /n
a = 10.967 (5) Å
b = 20.301 (5) Å
c = 11.072 (5) Å
β = 119.268 (5)°
V = 2150.4 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.12 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 = 0.941, T_max = 0.988
18535 measured reflections
3785 independent reflections
2955 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.108
S = 1.01
3785 reflections
304 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6⋯O9	0.91	2.09	2.903 (2)	148
C13—H13B⋯O7ⁱ	0.97	2.37	3.195 (3)	143
C14—H14B⋯O3ⁱⁱ	0.96	2.55	3.301 (3)	136
C15—H15A⋯O8ⁱⁱⁱ	0.97	2.52	3.275 (3)	134
C15—H15B⋯O8^iv	0.97	2.49	3.437 (3)	165
Symmetry codes: (i) x, y, z-1; (ii) x-1, y, z-1; (iii) x+1, y, z; (iv) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812030450/hb6883sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812030450/hb6883Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812030450/hb6883Isup3.cml

checkCIF report

Comment top

Barbiturates are pyrimidine derivatives and many of them are anticonvulsant agents (Tripathi, 2009). The crystalline barbiturate (Triethylammonium 5-(2,4,6-trinitrophenyl)barbiturate) reported by us (Kalaivani & Buvaneswari, 2010) also exhibits anticovulsant activity and is soluble in water.An attempt has now been made to increase the lipophilicity of the above mentioned barbiturate by introducing methyl groups to the nitrogen atoms of barbiturate anion (Scheme). Since the N—H protons of barbiturate residue are replaced by methyl groups, R²₂(8) motifs which have been normally observed in reported barbiturates (Kalaivani & Malarvizhi, 2009; Buvaneswari & Kalaivani, 2011; Babykala & Kalaivani, 2012), are absent in the crystal structure of the title barbiturate. The ORTEP view of the asymmetric unit of title molecule showing 40% probability displacement ellipsoids is shown in Fig.1. Weak N—H···O and C—H···O hydrogen bonds are noticed in the crystal structure which lead to supramolecular chains and these chains run along [001]direction [Fig.2]. In the title molecule, the two rings present in the anion moiety are not planar and the dihedral angle between them is 46.88 (8)°. The phenyl ring constituted by C1, C2, C3, C4, C5 and C6 carbon atoms and the nitro group with N2, O3 and O4 atoms are almost planar [dihedral angle 0.76 (3)°] which facilitates the delocalization of negative charge and thus the title molecular salt appears red in colour. The other two nitro groups (O1—N1—O2 and O5—N3—O6) make the dihedral angle 47.91 (2)° and 42.90 (1)° respectively with the aromatic ring.

Related literature top

For background to barbiturates, see: Tripathi (2009). For our recent work in this area, see: Kalaivani & Buvaneswari, 2010); Kalaivani & Malarvizhi (2009); Buvaneswari & Kalaivani (2011); Babykala & Kalaivani (2012).

Experimental top

Picrylchloride (1.3 g, 0.005 mol) was dissolved in 15 ml of absolute alcohol. 1,3-Dimethylbarbituric acid (0.8 g, 0.005 mol) was also dissolved in 15 ml of absolute alcohol.These two solution were mixed and to this 3 ml(0.03 mol) of analar grade triethylamine was added and shaken well for 6hrs. On standing maroon red crystals come out from this solution after 15 days. The crystals were filterded,powder well and washed with 30 ml of dry ether and recrystallized from absolute alcohol (yield of pure crystals 75%; m.pt; 458 K). Red block like single crystals suitable for X-ray studies were obtained by slow evapouration of ethanol at room temperature. The crystals obtained were non-hygroscopic and extraordinarly stable at room temperature. Solubility at 298 K: 19 g / dm³ (H₂O); 46 g / dm³ (EtOH); 131 g / dm³ (DMSO);6 g /dm³ (n-Octanol).

Structure description top

Computing details top

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

Figures top

	Fig. 1. The asymmetric unit of the title compound showing 40% probability displacement ellipsoids.
	Fig. 2. Packing view of title compound.

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

Crystal data top

C₆H₁₆N⁺·C₁₂H₈N₅O₉⁻	F(000) = 984
M_r = 468.43	D_x = 1.447 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.967 (5) Å	Cell parameters from 6627 reflections
b = 20.301 (5) Å	θ = 2.9–26.1°
c = 11.072 (5) Å	µ = 0.12 mm⁻¹
β = 119.268 (5)°	T = 293 K
V = 2150.4 (15) Å³	Block, red
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3785 independent reflections
Radiation source: fine-focus sealed tube	2955 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω and φ scan	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −13→12
T_min = 0.941, T_max = 0.988	k = −24→24
18535 measured reflections	l = −13→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.108	w = 1/[σ²(F_o²) + (0.0548P)² + 0.6716P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
3785 reflections	Δρ_max = 0.28 e Å⁻³
304 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0019 (6)

Crystal data top

C₆H₁₆N⁺·C₁₂H₈N₅O₉⁻	V = 2150.4 (15) Å³
M_r = 468.43	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.967 (5) Å	µ = 0.12 mm⁻¹
b = 20.301 (5) Å	T = 293 K
c = 11.072 (5) Å	0.30 × 0.20 × 0.20 mm
β = 119.268 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3785 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	2955 reflections with I > 2σ(I)
T_min = 0.941, T_max = 0.988	R_int = 0.029
18535 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.01	Δρ_max = 0.28 e Å⁻³
3785 reflections	Δρ_min = −0.16 e Å⁻³
304 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	0.88311 (17)	0.10654 (8)	0.91121 (17)	0.0341 (4)
C2	1.02255 (18)	0.12113 (9)	0.98506 (17)	0.0362 (4)
H2	1.0876	0.0978	0.9710	0.043*
C3	1.06380 (16)	0.17129 (9)	1.08071 (16)	0.0335 (4)
C4	0.96883 (17)	0.20600 (9)	1.10282 (17)	0.0354 (4)
H4	0.9979	0.2388	1.1700	0.042*
C5	0.82951 (17)	0.19082 (8)	1.02269 (16)	0.0330 (4)
C6	0.77688 (17)	0.14087 (8)	0.92164 (16)	0.0318 (4)
C7	0.62923 (17)	0.12556 (9)	0.83656 (16)	0.0345 (4)
C8	0.54703 (18)	0.11973 (9)	0.90224 (17)	0.0378 (4)
C9	0.34306 (18)	0.09753 (9)	0.67628 (17)	0.0369 (4)
C10	0.57272 (17)	0.11594 (8)	0.69361 (17)	0.0344 (4)
C11	0.3184 (2)	0.09483 (14)	0.8813 (2)	0.0681 (7)
H11A	0.2885	0.1368	0.8971	0.102*
H11B	0.3712	0.0723	0.9679	0.102*
H11C	0.2381	0.0689	0.8211	0.102*
C12	0.3617 (2)	0.09733 (12)	0.46746 (19)	0.0578 (6)
H12A	0.3738	0.0528	0.4458	0.087*
H12B	0.4041	0.1271	0.4313	0.087*
H12C	0.2638	0.1070	0.4266	0.087*
C13	0.63642 (18)	0.12726 (9)	0.33536 (18)	0.0409 (4)
H13A	0.5743	0.1558	0.3506	0.049*
H13B	0.6456	0.1453	0.2591	0.049*
C14	0.5725 (2)	0.06017 (10)	0.2963 (2)	0.0527 (5)
H14A	0.6219	0.0345	0.2612	0.079*
H14B	0.4762	0.0641	0.2263	0.079*
H14C	0.5783	0.0388	0.3763	0.079*
C15	0.87815 (18)	0.07822 (9)	0.45773 (18)	0.0420 (4)
H15A	0.9655	0.0800	0.5444	0.050*
H15B	0.8402	0.0342	0.4487	0.050*
C16	0.9074 (2)	0.09033 (12)	0.3404 (2)	0.0554 (5)
H16A	0.8216	0.0880	0.2541	0.083*
H16B	0.9710	0.0575	0.3418	0.083*
H16C	0.9481	0.1332	0.3504	0.083*
C17	0.8343 (2)	0.19556 (10)	0.4964 (2)	0.0514 (5)
H17A	0.8565	0.2100	0.4259	0.062*
H17B	0.7625	0.2246	0.4930	0.062*
C18	0.9621 (2)	0.20199 (12)	0.6351 (2)	0.0648 (6)
H18A	0.9427	0.1854	0.7052	0.097*
H18B	0.9885	0.2475	0.6530	0.097*
H18C	1.0371	0.1772	0.6360	0.097*
N1	0.85117 (16)	0.04632 (8)	0.82617 (16)	0.0453 (4)
N2	1.21193 (15)	0.18730 (8)	1.16185 (15)	0.0395 (4)
N3	0.73551 (15)	0.23498 (7)	1.04510 (15)	0.0397 (4)
N4	0.40581 (14)	0.10460 (8)	0.81685 (14)	0.0403 (4)
N5	0.42801 (14)	0.10512 (7)	0.61771 (14)	0.0373 (4)
N6	0.77754 (14)	0.12699 (7)	0.46335 (14)	0.0370 (3)
H6	0.7634	0.1141	0.5343	0.044*
O1	0.77641 (16)	0.00505 (7)	0.83646 (16)	0.0609 (4)
O2	0.90781 (17)	0.03998 (8)	0.75520 (16)	0.0690 (5)
O3	1.29408 (13)	0.15560 (8)	1.14104 (15)	0.0588 (4)
O4	1.24725 (14)	0.23153 (8)	1.24621 (15)	0.0605 (4)
O5	0.77284 (14)	0.25027 (7)	1.16504 (13)	0.0534 (4)
O6	0.63133 (14)	0.25617 (7)	0.94531 (14)	0.0532 (4)
O7	0.59132 (14)	0.12529 (8)	1.02758 (13)	0.0545 (4)
O8	0.21962 (12)	0.08442 (7)	0.60642 (13)	0.0507 (4)
O9	0.63886 (13)	0.11793 (7)	0.62877 (12)	0.0470 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0351 (9)	0.0377 (9)	0.0296 (9)	−0.0007 (7)	0.0159 (7)	−0.0015 (7)
C2	0.0339 (9)	0.0426 (10)	0.0369 (9)	0.0050 (7)	0.0209 (8)	0.0019 (8)
C3	0.0277 (8)	0.0425 (10)	0.0299 (8)	0.0000 (7)	0.0137 (7)	0.0021 (7)
C4	0.0359 (9)	0.0407 (10)	0.0294 (9)	−0.0018 (7)	0.0160 (7)	−0.0026 (7)
C5	0.0326 (9)	0.0397 (10)	0.0303 (9)	0.0024 (7)	0.0183 (7)	0.0007 (7)
C6	0.0331 (9)	0.0404 (9)	0.0245 (8)	−0.0003 (7)	0.0160 (7)	0.0039 (7)
C7	0.0305 (9)	0.0446 (10)	0.0288 (9)	−0.0012 (7)	0.0147 (7)	0.0001 (7)
C8	0.0336 (9)	0.0498 (11)	0.0305 (9)	−0.0024 (8)	0.0161 (8)	−0.0021 (7)
C9	0.0310 (10)	0.0413 (10)	0.0356 (9)	0.0009 (7)	0.0143 (8)	−0.0021 (7)
C10	0.0328 (9)	0.0406 (10)	0.0301 (9)	−0.0002 (7)	0.0157 (8)	0.0008 (7)
C11	0.0449 (12)	0.119 (2)	0.0525 (13)	−0.0154 (12)	0.0337 (11)	−0.0137 (12)
C12	0.0460 (12)	0.0905 (17)	0.0299 (10)	−0.0027 (11)	0.0132 (9)	−0.0005 (10)
C13	0.0357 (10)	0.0494 (11)	0.0360 (10)	0.0086 (8)	0.0162 (8)	0.0042 (8)
C14	0.0371 (10)	0.0581 (13)	0.0529 (12)	0.0011 (9)	0.0142 (9)	−0.0018 (10)
C15	0.0344 (10)	0.0454 (11)	0.0410 (10)	0.0055 (8)	0.0145 (8)	0.0017 (8)
C16	0.0458 (12)	0.0736 (15)	0.0521 (12)	0.0104 (10)	0.0281 (10)	−0.0039 (10)
C17	0.0601 (13)	0.0454 (11)	0.0546 (12)	−0.0036 (9)	0.0327 (11)	−0.0063 (9)
C18	0.0546 (13)	0.0687 (15)	0.0713 (15)	−0.0167 (11)	0.0310 (12)	−0.0205 (12)
N1	0.0412 (9)	0.0464 (10)	0.0439 (9)	0.0012 (7)	0.0173 (8)	−0.0074 (7)
N2	0.0323 (8)	0.0496 (9)	0.0372 (8)	−0.0013 (7)	0.0176 (7)	0.0010 (7)
N3	0.0360 (8)	0.0470 (9)	0.0385 (9)	0.0034 (7)	0.0202 (7)	−0.0026 (7)
N4	0.0307 (8)	0.0596 (10)	0.0345 (8)	−0.0039 (7)	0.0190 (7)	−0.0033 (7)
N5	0.0305 (8)	0.0527 (9)	0.0261 (7)	−0.0019 (6)	0.0118 (6)	−0.0007 (6)
N6	0.0377 (8)	0.0433 (8)	0.0336 (8)	0.0024 (6)	0.0203 (7)	0.0031 (6)
O1	0.0591 (9)	0.0453 (8)	0.0744 (10)	−0.0100 (7)	0.0295 (8)	−0.0083 (7)
O2	0.0717 (10)	0.0792 (11)	0.0714 (10)	−0.0022 (8)	0.0470 (9)	−0.0295 (8)
O3	0.0326 (7)	0.0740 (10)	0.0692 (10)	0.0027 (7)	0.0244 (7)	−0.0134 (8)
O4	0.0431 (8)	0.0759 (10)	0.0599 (9)	−0.0148 (7)	0.0232 (7)	−0.0280 (8)
O5	0.0512 (8)	0.0702 (10)	0.0411 (8)	0.0074 (7)	0.0244 (6)	−0.0139 (7)
O6	0.0412 (8)	0.0656 (9)	0.0472 (8)	0.0187 (6)	0.0172 (7)	0.0046 (7)
O7	0.0452 (8)	0.0924 (11)	0.0289 (7)	−0.0134 (7)	0.0205 (6)	−0.0051 (6)
O8	0.0282 (7)	0.0692 (9)	0.0474 (8)	−0.0049 (6)	0.0127 (6)	−0.0074 (6)
O9	0.0398 (7)	0.0745 (9)	0.0324 (7)	−0.0049 (6)	0.0220 (6)	−0.0027 (6)

Geometric parameters (Å, º) top

C1—C2	1.368 (2)	C13—C14	1.496 (3)
C1—C6	1.410 (2)	C13—N6	1.503 (2)
C1—N1	1.477 (2)	C13—H13A	0.9700
C2—C3	1.376 (2)	C13—H13B	0.9700
C2—H2	0.9300	C14—H14A	0.9600
C3—C4	1.375 (2)	C14—H14B	0.9600
C3—N2	1.458 (2)	C14—H14C	0.9600
C4—C5	1.375 (2)	C15—C16	1.502 (3)
C4—H4	0.9300	C15—N6	1.506 (2)
C5—C6	1.408 (2)	C15—H15A	0.9700
C5—N3	1.476 (2)	C15—H15B	0.9700
C6—C7	1.454 (2)	C16—H16A	0.9600
C7—C10	1.403 (2)	C16—H16B	0.9600
C7—C8	1.413 (2)	C16—H16C	0.9600
C8—O7	1.231 (2)	C17—C18	1.494 (3)
C8—N4	1.398 (2)	C17—N6	1.496 (2)
C9—O8	1.216 (2)	C17—H17A	0.9700
C9—N4	1.367 (2)	C17—H17B	0.9700
C9—N5	1.379 (2)	C18—H18A	0.9600
C10—O9	1.246 (2)	C18—H18B	0.9600
C10—N5	1.403 (2)	C18—H18C	0.9600
C11—N4	1.461 (2)	N1—O1	1.216 (2)
C11—H11A	0.9600	N1—O2	1.224 (2)
C11—H11B	0.9600	N2—O4	1.214 (2)
C11—H11C	0.9600	N2—O3	1.2174 (19)
C12—N5	1.462 (2)	N3—O6	1.2153 (19)
C12—H12A	0.9600	N3—O5	1.2231 (19)
C12—H12B	0.9600	N6—H6	0.9100
C12—H12C	0.9600

C2—C1—C6	124.81 (16)	H14A—C14—H14B	109.5
C2—C1—N1	114.05 (15)	C13—C14—H14C	109.5
C6—C1—N1	120.89 (15)	H14A—C14—H14C	109.5
C1—C2—C3	118.09 (15)	H14B—C14—H14C	109.5
C1—C2—H2	121.0	C16—C15—N6	113.47 (15)
C3—C2—H2	121.0	C16—C15—H15A	108.9
C4—C3—C2	121.56 (15)	N6—C15—H15A	108.9
C4—C3—N2	119.27 (15)	C16—C15—H15B	108.9
C2—C3—N2	119.16 (15)	N6—C15—H15B	108.9
C3—C4—C5	118.02 (16)	H15A—C15—H15B	107.7
C3—C4—H4	121.0	C15—C16—H16A	109.5
C5—C4—H4	121.0	C15—C16—H16B	109.5
C4—C5—C6	124.66 (15)	H16A—C16—H16B	109.5
C4—C5—N3	113.74 (15)	C15—C16—H16C	109.5
C6—C5—N3	121.49 (14)	H16A—C16—H16C	109.5
C5—C6—C1	112.77 (15)	H16B—C16—H16C	109.5
C5—C6—C7	124.26 (15)	C18—C17—N6	113.69 (18)
C1—C6—C7	122.98 (15)	C18—C17—H17A	108.8
C10—C7—C8	121.86 (15)	N6—C17—H17A	108.8
C10—C7—C6	119.90 (15)	C18—C17—H17B	108.8
C8—C7—C6	118.23 (15)	N6—C17—H17B	108.8
O7—C8—N4	118.59 (15)	H17A—C17—H17B	107.7
O7—C8—C7	124.97 (16)	C17—C18—H18A	109.5
N4—C8—C7	116.41 (15)	C17—C18—H18B	109.5
O8—C9—N4	122.11 (16)	H18A—C18—H18B	109.5
O8—C9—N5	121.55 (16)	C17—C18—H18C	109.5
N4—C9—N5	116.33 (15)	H18A—C18—H18C	109.5
O9—C10—C7	125.81 (16)	H18B—C18—H18C	109.5
O9—C10—N5	117.82 (15)	O1—N1—O2	124.41 (17)
C7—C10—N5	116.35 (15)	O1—N1—C1	118.11 (16)
N4—C11—H11A	109.5	O2—N1—C1	117.37 (16)
N4—C11—H11B	109.5	O4—N2—O3	123.31 (15)
H11A—C11—H11B	109.5	O4—N2—C3	118.63 (15)
N4—C11—H11C	109.5	O3—N2—C3	118.05 (15)
H11A—C11—H11C	109.5	O6—N3—O5	124.33 (15)
H11B—C11—H11C	109.5	O6—N3—C5	119.06 (14)
N5—C12—H12A	109.5	O5—N3—C5	116.51 (14)
N5—C12—H12B	109.5	C9—N4—C8	124.58 (14)
H12A—C12—H12B	109.5	C9—N4—C11	117.14 (15)
N5—C12—H12C	109.5	C8—N4—C11	118.28 (15)
H12A—C12—H12C	109.5	C9—N5—C10	124.20 (14)
H12B—C12—H12C	109.5	C9—N5—C12	116.65 (15)
C14—C13—N6	112.98 (15)	C10—N5—C12	119.06 (15)
C14—C13—H13A	109.0	C17—N6—C13	109.94 (14)
N6—C13—H13A	109.0	C17—N6—C15	113.33 (14)
C14—C13—H13B	109.0	C13—N6—C15	113.64 (14)
N6—C13—H13B	109.0	C17—N6—H6	106.5
H13A—C13—H13B	107.8	C13—N6—H6	106.5
C13—C14—H14A	109.5	C15—N6—H6	106.5
C13—C14—H14B	109.5

C6—C1—C2—C3	2.7 (3)	C6—C1—N1—O2	138.16 (18)
N1—C1—C2—C3	−171.73 (15)	C4—C3—N2—O4	−0.7 (2)
C1—C2—C3—C4	0.2 (3)	C2—C3—N2—O4	−179.81 (16)
C1—C2—C3—N2	179.31 (15)	C4—C3—N2—O3	179.52 (16)
C2—C3—C4—C5	−2.3 (3)	C2—C3—N2—O3	0.4 (2)
N2—C3—C4—C5	178.59 (15)	C4—C5—N3—O6	135.01 (17)
C3—C4—C5—C6	1.8 (3)	C6—C5—N3—O6	−41.4 (2)
C3—C4—C5—N3	−174.45 (15)	C4—C5—N3—O5	−41.5 (2)
C4—C5—C6—C1	0.7 (2)	C6—C5—N3—O5	142.10 (16)
N3—C5—C6—C1	176.70 (14)	O8—C9—N4—C8	−179.90 (17)
C4—C5—C6—C7	−179.45 (16)	N5—C9—N4—C8	1.0 (3)
N3—C5—C6—C7	−3.4 (2)	O8—C9—N4—C11	0.8 (3)
C2—C1—C6—C5	−3.0 (2)	N5—C9—N4—C11	−178.25 (18)
N1—C1—C6—C5	171.01 (15)	O7—C8—N4—C9	179.50 (17)
C2—C1—C6—C7	177.13 (16)	C7—C8—N4—C9	−2.3 (3)
N1—C1—C6—C7	−8.8 (2)	O7—C8—N4—C11	−1.2 (3)
C5—C6—C7—C10	134.21 (17)	C7—C8—N4—C11	176.98 (18)
C1—C6—C7—C10	−46.0 (2)	O8—C9—N5—C10	−175.62 (17)
C5—C6—C7—C8	−46.9 (2)	N4—C9—N5—C10	3.4 (2)
C1—C6—C7—C8	132.98 (18)	O8—C9—N5—C12	0.7 (3)
C10—C7—C8—O7	177.32 (18)	N4—C9—N5—C12	179.73 (17)
C6—C7—C8—O7	−1.6 (3)	O9—C10—N5—C9	175.68 (16)
C10—C7—C8—N4	−0.7 (3)	C7—C10—N5—C9	−6.2 (2)
C6—C7—C8—N4	−179.65 (16)	O9—C10—N5—C12	−0.5 (2)
C8—C7—C10—O9	−177.38 (17)	C7—C10—N5—C12	177.61 (17)
C6—C7—C10—O9	1.5 (3)	C18—C17—N6—C13	169.79 (16)
C8—C7—C10—N5	4.7 (2)	C18—C17—N6—C15	−61.8 (2)
C6—C7—C10—N5	−176.45 (15)	C14—C13—N6—C17	−179.66 (16)
C2—C1—N1—O1	129.19 (17)	C14—C13—N6—C15	52.1 (2)
C6—C1—N1—O1	−45.4 (2)	C16—C15—N6—C17	−66.4 (2)
C2—C1—N1—O2	−47.2 (2)	C16—C15—N6—C13	60.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···O9	0.91	2.09	2.903 (2)	148
C13—H13B···O7ⁱ	0.97	2.37	3.195 (3)	143
C14—H14B···O3ⁱⁱ	0.96	2.55	3.301 (3)	136
C15—H15A···O8ⁱⁱⁱ	0.97	2.52	3.275 (3)	134
C15—H15B···O8^iv	0.97	2.49	3.437 (3)	165

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

Experimental details

Crystal data
Chemical formula	C₆H₁₆N⁺·C₁₂H₈N₅O₉⁻
M_r	468.43
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.967 (5), 20.301 (5), 11.072 (5)
β (°)	119.268 (5)
V (Å³)	2150.4 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.941, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	18535, 3785, 2955
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.108, 1.01
No. of reflections	3785
No. of parameters	304
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.16

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···O9	0.91	2.09	2.903 (2)	148.2
C13—H13B···O7ⁱ	0.97	2.37	3.195 (3)	143
C14—H14B···O3ⁱⁱ	0.96	2.55	3.301 (3)	136
C15—H15A···O8ⁱⁱⁱ	0.97	2.52	3.275 (3)	134
C15—H15B···O8^iv	0.97	2.49	3.437 (3)	165

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

Acknowledgements

The authors thank SAIF, IIT Madras, for the data collection.

References

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