2-Methyl­pyridinium 5-(2,4-dinitro­phen­yl)-1,3-dimethyl­barbiturate

Sridevi, G.; Kalaivani, D.

doi:10.1107/S1600536812009440

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1044

doi:10.1107/S1600536812009440

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2-Methylpyridinium 5-(2,4-dinitrophenyl)-1,3-dimethylbarbiturate

Gunaseelan Sridevi ^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 26 November 2011; accepted 4 March 2012; online 14 March 2012)

In the title molecular salt [systematic name: 2-methylpyridinium 5-(2,4-dinitrophenyl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate], C₆H₈N⁺·C₁₂H₉N₄O₇⁻, the cation and anion are linked a through strong N—H⋯O hydrogen bond. In the crystal, C—H⋯O interactions link the ions, generating a chain along [010].

Related literature

For the biological properties of molecules containing pyridine and pyrimidine units, see: Terekhova & Scriba (2007 ); Comins et al. (2008 ); Hueso et al. (2003 ); Jain et al. (2006 ). For the structures of barbiturates similar to the title compound, see: Kalaivani & Malarvizhi (2009 ); Kalaivani & Buvaneswari (2010 ); Buvaneswari & Kalaivani (2011 ).

Experimental

Crystal data

C₆H₈N⁺·C₁₂H₉N₄O₇⁻
M_r = 415.37
Monoclinic, P 2₁ /n
a = 12.8242 (8) Å
b = 7.0696 (5) Å
c = 21.5409 (14) Å
β = 101.029 (2)°
V = 1916.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.917, T_max = 0.983
3527 measured reflections
3527 independent reflections
2790 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.099
S = 1.04
3527 reflections
275 parameters
H-atom parameters constrained
Δρ_max = 0.15 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
N5—H5A⋯O3	0.86	1.82	2.6645 (16)	168
C13—H13B⋯O5ⁱ	0.96	2.42	3.340 (2)	161
C13—H13C⋯O1ⁱⁱ	0.96	2.42	3.160 (2)	134
C15—H15⋯O2ⁱⁱⁱ	0.93	2.29	3.021 (2)	135
C16—H16⋯O6^iv	0.93	2.58	3.323 (2)	138
C17—H17⋯O1^v	0.93	2.52	3.303 (2)	143
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) -x+2, -y+1, -z+1; (v) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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: 10.1107/S1600536812009440/bv2197sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812009440/bv2197Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812009440/bv2197Isup3.cml

checkCIF report

Comment top

Many molecules containing the pyridine moiety exhibit notable biological activity (Terekhova & Scriba, 2007; Comins et al., 2008). Molecules with pyrimidine ring residues are also biologically active (Hueso et al., 2003; Jain et al., 2006). The title molecular salt comprises of both pyrimidine (barbiturate moiety) and pyridine (2-methyl pyridinium) moieties and hence expected to have significant biological activity. Good crystallinity of the title compound prompted us to undertake single-crystal X-ray studies. The bond lengths and bond angles of the barbiturate residue of the molecular salt reported in the present article are compatible with those of related barbiturates synthesized in our laboratory earlier (Kalaivani & Malarvizhi, 2009; Kalaivani & Buvaneswari, 2010; Buvaneswari & Kalaivani, 2011). The structure of the molecular salt of the present work is shown in scheme 1. The ORTEP view showing 30% probability displacement ellipsoids is indicated in Fig.1. In the title molecule, the one dimensional zigzag chains which run along [010] direction are linked through C13—H13···O1, C17—H17···O1, C16—H16···O6, C13—H13···O3 and C15—H15···O2 weak interactions thus generating a three dimensional network and hence constituting the molecular packing of the crystal (Fig. 2). The 2,4-dinitrophenyl ring and 1,3-dimethylbarbiturate ring of the title molecule are not perfectly planar and the dihedral angle observed between them is 44.54 (2)degree.

Related literature top

For the biological properties of molecules containing pyridine and pyrimidine units, see: Terekhova & Scriba (2007); Comins et al. (2008); Hueso et al. (2003); Jain et al. (2006). For the structures of barbiturates similar to the title compound, see: Kalaivani & Malarvizhi (2009); Kalaivani & Buvaneswari (2010); Buvaneswari & Kalaivani (2011).

Experimental top

1-Chloro-2,4-dinitrobenzene(2.02 g,0.01 mol) was dissolved in 20 ml of ethanol. 1,3-Dimethylbarbituric acid (1.56 g,0.01 mol) was also dissolved in 15 ml of ethanol. These two solutions were mixed and to this mixture a five fold excess of 2-methylpyridine (4.65 g, 0.05 mol) was added and the resulting blood red coloured solution was shaken well for about three hours and kept as such at 25 /%C. Dark shiny maroon red coloured crystals were deposited from the solution after seventy two hours. The crystals were filtered and washed with 30 ml of ether. The crystals were powdered well and washed with 40 ml of ether to remove the unreacted reactants and finally with 10 ml of ethanol. The pure powder was recrystallized from hot ethanol (Yield: 75%; m.p.; 451 K). The crystals for X-ray analysis were obtained by slow evaporation of ethanol at room temperature.

Structure description top

For the biological properties of molecules containing pyridine and pyrimidine units, see: Terekhova & Scriba (2007); Comins et al. (2008); Hueso et al. (2003); Jain et al. (2006). For the structures of barbiturates similar to the title compound, see: Kalaivani & Malarvizhi (2009); Kalaivani & Buvaneswari (2010); Buvaneswari & Kalaivani (2011).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and 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: PLATON (Spek, 2009).

Figures top

	Fig. 1. The asymmetric unit of title molecule showing 30% probability displacement ellipsoids.
	Fig. 2. Packing view of title molecule showing the chains in the [010] direction.

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

Crystal data top

C₆H₈N⁺·C₁₂H₉N₄O₇⁻	F(000) = 864
M_r = 415.37	D_x = 1.439 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6197 reflections
a = 12.8242 (8) Å	θ = 2.9–25.3°
b = 7.0696 (5) Å	µ = 0.11 mm⁻¹
c = 21.5409 (14) Å	T = 293 K
β = 101.029 (2)°	Block, red
V = 1916.9 (2) Å³	0.30 × 0.25 × 0.15 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3527 independent reflections
Radiation source: fine-focus sealed tube	2790 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.000
ω and φ scan	θ_max = 25.4°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −15→15
T_min = 0.917, T_max = 0.983	k = 0→8
3527 measured reflections	l = 0→25

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.045P)² + 0.4365P] where P = (F_o² + 2F_c²)/3
3527 reflections	(Δ/σ)_max < 0.001
275 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₆H₈N⁺·C₁₂H₉N₄O₇⁻	V = 1916.9 (2) Å³
M_r = 415.37	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.8242 (8) Å	µ = 0.11 mm⁻¹
b = 7.0696 (5) Å	T = 293 K
c = 21.5409 (14) Å	0.30 × 0.25 × 0.15 mm
β = 101.029 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3527 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2790 reflections with I > 2σ(I)
T_min = 0.917, T_max = 0.983	R_int = 0.000
3527 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.04	Δρ_max = 0.15 e Å⁻³
3527 reflections	Δρ_min = −0.17 e Å⁻³
275 parameters

Special details top

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	Occ. (<1)
O1	0.25790 (8)	0.59806 (19)	0.13771 (6)	0.0652 (4)
O2	0.58313 (8)	0.84817 (17)	0.13910 (5)	0.0521 (3)
O3	0.49962 (8)	0.55652 (17)	0.31960 (5)	0.0550 (3)
O4	0.53244 (10)	0.9752 (2)	0.33842 (6)	0.0694 (4)
O5	0.60991 (12)	0.8263 (2)	0.42199 (6)	0.0831 (4)
O6	0.98964 (12)	0.8224 (3)	0.43012 (8)	0.1054 (6)
O7	1.04967 (11)	0.7451 (2)	0.34758 (8)	0.0851 (5)
N1	0.41979 (10)	0.72838 (19)	0.13974 (6)	0.0457 (3)
N2	0.37859 (9)	0.58307 (18)	0.22914 (6)	0.0453 (3)
N3	0.60166 (12)	0.8717 (2)	0.36639 (6)	0.0552 (4)
N4	0.97702 (13)	0.7814 (2)	0.37450 (9)	0.0678 (5)
C1	0.38684 (15)	0.7872 (3)	0.07370 (8)	0.0711 (6)
H1A	0.4128	0.9125	0.0685	0.107*	0.62 (3)
H1B	0.3107	0.7867	0.0625	0.107*	0.62 (3)
H1C	0.4154	0.7011	0.0468	0.107*	0.62 (3)
H1C1	0.4484	0.8199	0.0567	0.107*	0.38 (3)
H1C2	0.3408	0.8951	0.0715	0.107*	0.38 (3)
H1C3	0.3497	0.6853	0.0496	0.107*	0.38 (3)
C2	0.34662 (11)	0.6346 (2)	0.16695 (7)	0.0461 (4)
C3	0.30525 (14)	0.4711 (3)	0.25827 (10)	0.0714 (6)
H3A	0.2900	0.5371	0.2945	0.107*
H3B	0.3370	0.3510	0.2713	0.107*
H3C	0.2405	0.4516	0.2282	0.107*
C4	0.48022 (11)	0.6176 (2)	0.26412 (7)	0.0404 (3)
C5	0.55251 (10)	0.71463 (19)	0.23462 (6)	0.0363 (3)
C6	0.52461 (11)	0.7686 (2)	0.17015 (7)	0.0390 (3)
C7	0.65998 (11)	0.74854 (18)	0.26967 (6)	0.0351 (3)
C8	0.68428 (11)	0.8054 (2)	0.33312 (7)	0.0412 (3)
C9	0.78652 (12)	0.8162 (2)	0.36788 (7)	0.0476 (4)
H9	0.7991	0.8498	0.4104	0.057*
C10	0.86841 (12)	0.7759 (2)	0.33778 (8)	0.0472 (4)
C11	0.85129 (12)	0.7277 (2)	0.27469 (8)	0.0466 (4)
H11	0.9082	0.7047	0.2547	0.056*
C12	0.74849 (11)	0.7141 (2)	0.24194 (7)	0.0405 (3)
H12	0.7372	0.6805	0.1994	0.049*
N5	0.61757 (9)	0.36331 (18)	0.41383 (6)	0.0434 (3)
H5A	0.5829	0.4153	0.3800	0.052*
C13	0.44507 (13)	0.3047 (3)	0.43878 (8)	0.0616 (5)
H13A	0.4246	0.4261	0.4205	0.092*
H13B	0.4158	0.2883	0.4762	0.092*
H13C	0.4187	0.2072	0.4089	0.092*
C14	0.56244 (12)	0.2933 (2)	0.45537 (7)	0.0447 (4)
C15	0.72358 (12)	0.3570 (2)	0.42194 (8)	0.0530 (4)
H15	0.7579	0.4067	0.3913	0.064*
C16	0.78080 (14)	0.2779 (3)	0.47504 (9)	0.0638 (5)
H16	0.8545	0.2717	0.4811	0.077*
C17	0.72821 (16)	0.2074 (3)	0.51962 (9)	0.0686 (5)
H17	0.7664	0.1546	0.5566	0.082*
C18	0.61948 (15)	0.2143 (3)	0.50993 (8)	0.0602 (5)
H18	0.5841	0.1655	0.5403	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0384 (6)	0.0833 (9)	0.0665 (7)	−0.0017 (6)	−0.0081 (5)	−0.0018 (7)
O2	0.0521 (6)	0.0640 (7)	0.0406 (6)	−0.0043 (5)	0.0101 (5)	0.0080 (5)
O3	0.0508 (6)	0.0660 (8)	0.0458 (6)	−0.0074 (5)	0.0030 (5)	0.0188 (5)
O4	0.0682 (8)	0.0715 (9)	0.0722 (8)	0.0120 (7)	0.0225 (7)	−0.0144 (7)
O5	0.1004 (10)	0.1142 (12)	0.0405 (7)	−0.0185 (9)	0.0278 (7)	−0.0079 (7)
O6	0.0762 (10)	0.1480 (16)	0.0739 (10)	−0.0106 (10)	−0.0311 (8)	−0.0053 (10)
O7	0.0414 (7)	0.0957 (11)	0.1117 (12)	−0.0104 (7)	−0.0020 (8)	0.0226 (9)
N1	0.0428 (7)	0.0528 (8)	0.0379 (7)	0.0017 (6)	−0.0018 (5)	0.0019 (6)
N2	0.0368 (6)	0.0482 (8)	0.0497 (7)	−0.0033 (5)	0.0050 (5)	0.0045 (6)
N3	0.0637 (9)	0.0614 (9)	0.0440 (8)	−0.0126 (8)	0.0187 (7)	−0.0133 (7)
N4	0.0493 (9)	0.0633 (10)	0.0807 (12)	−0.0116 (7)	−0.0128 (8)	0.0157 (9)
C1	0.0662 (11)	0.0939 (15)	0.0451 (10)	−0.0040 (10)	−0.0097 (8)	0.0135 (10)
C2	0.0386 (8)	0.0465 (9)	0.0505 (9)	0.0043 (7)	0.0021 (7)	−0.0032 (7)
C3	0.0498 (10)	0.0804 (14)	0.0828 (13)	−0.0159 (9)	0.0093 (9)	0.0196 (11)
C4	0.0389 (7)	0.0388 (8)	0.0423 (8)	0.0018 (6)	0.0048 (6)	0.0017 (6)
C5	0.0374 (7)	0.0344 (7)	0.0360 (7)	0.0018 (6)	0.0047 (6)	−0.0009 (6)
C6	0.0398 (7)	0.0373 (8)	0.0393 (8)	0.0034 (6)	0.0059 (6)	−0.0030 (6)
C7	0.0399 (7)	0.0289 (7)	0.0356 (7)	−0.0002 (6)	0.0050 (6)	0.0019 (5)
C8	0.0468 (8)	0.0383 (8)	0.0384 (8)	−0.0052 (6)	0.0084 (6)	0.0009 (6)
C9	0.0556 (9)	0.0452 (9)	0.0378 (8)	−0.0107 (7)	−0.0018 (7)	0.0024 (7)
C10	0.0413 (8)	0.0397 (8)	0.0541 (9)	−0.0072 (7)	−0.0073 (7)	0.0089 (7)
C11	0.0395 (8)	0.0399 (8)	0.0607 (10)	0.0014 (6)	0.0102 (7)	0.0050 (7)
C12	0.0425 (7)	0.0374 (8)	0.0411 (8)	0.0030 (6)	0.0062 (6)	−0.0019 (6)
N5	0.0440 (7)	0.0465 (7)	0.0380 (6)	−0.0003 (6)	0.0035 (5)	0.0016 (6)
C13	0.0480 (9)	0.0805 (13)	0.0576 (10)	−0.0059 (9)	0.0132 (8)	0.0028 (9)
C14	0.0498 (8)	0.0434 (9)	0.0402 (8)	−0.0049 (7)	0.0070 (7)	−0.0030 (7)
C15	0.0449 (9)	0.0567 (10)	0.0574 (10)	−0.0032 (7)	0.0097 (7)	−0.0012 (8)
C16	0.0472 (9)	0.0676 (12)	0.0707 (12)	0.0041 (8)	−0.0040 (9)	−0.0013 (10)
C17	0.0714 (12)	0.0662 (12)	0.0584 (11)	0.0080 (10)	−0.0121 (9)	0.0101 (9)
C18	0.0725 (12)	0.0598 (11)	0.0466 (9)	−0.0047 (9)	0.0071 (8)	0.0110 (8)

Geometric parameters (Å, º) top

O1—C2	1.2181 (17)	C5—C7	1.4591 (18)
O2—C6	1.2325 (17)	C7—C12	1.401 (2)
O3—C4	1.2501 (17)	C7—C8	1.4014 (19)
O4—N3	1.2174 (19)	C8—C9	1.382 (2)
O5—N3	1.2248 (18)	C9—C10	1.366 (2)
O6—N4	1.213 (2)	C9—H9	0.9300
O7—N4	1.215 (2)	C10—C11	1.377 (2)
N1—C2	1.369 (2)	C11—C12	1.374 (2)
N1—C6	1.4071 (18)	C11—H11	0.9300
N1—C1	1.465 (2)	C12—H12	0.9300
N2—C2	1.3728 (19)	N5—C14	1.3370 (19)
N2—C4	1.3966 (18)	N5—C15	1.3379 (19)
N2—C3	1.460 (2)	N5—H5A	0.8600
N3—C8	1.465 (2)	C13—C14	1.481 (2)
N4—C10	1.465 (2)	C13—H13A	0.9600
C1—H1A	0.9600	C13—H13B	0.9600
C1—H1B	0.9600	C13—H13C	0.9600
C1—H1C	0.9600	C14—C18	1.378 (2)
C1—H1C1	0.9599	C15—C16	1.356 (2)
C1—H1C2	0.9600	C15—H15	0.9300
C1—H1C3	0.9600	C16—C17	1.369 (3)
C3—H3A	0.9600	C16—H16	0.9300
C3—H3B	0.9600	C17—C18	1.371 (3)
C3—H3C	0.9600	C17—H17	0.9300
C4—C5	1.400 (2)	C18—H18	0.9300
C5—C6	1.418 (2)

C2—N1—C6	124.79 (12)	C8—C7—C5	124.30 (13)
C2—N1—C1	117.35 (13)	C9—C8—C7	123.72 (14)
C6—N1—C1	117.85 (13)	C9—C8—N3	114.66 (13)
C2—N2—C4	123.63 (13)	C7—C8—N3	121.48 (13)
C2—N2—C3	117.81 (13)	C10—C9—C8	117.86 (14)
C4—N2—C3	118.32 (13)	C10—C9—H9	121.1
O4—N3—O5	124.05 (15)	C8—C9—H9	121.1
O4—N3—C8	118.52 (13)	C9—C10—C11	121.88 (13)
O5—N3—C8	117.33 (15)	C9—C10—N4	118.44 (15)
O6—N4—O7	123.52 (16)	C11—C10—N4	119.67 (16)
O6—N4—C10	118.22 (18)	C12—C11—C10	118.68 (15)
O7—N4—C10	118.26 (17)	C12—C11—H11	120.7
N1—C1—H1A	109.5	C10—C11—H11	120.7
N1—C1—H1B	109.5	C11—C12—C7	123.00 (14)
N1—C1—H1C	109.5	C11—C12—H12	118.5
N1—C1—H1C1	109.5	C7—C12—H12	118.5
N1—C1—H1C2	109.5	C14—N5—C15	123.68 (13)
H1C1—C1—H1C2	109.5	C14—N5—H5A	118.2
N1—C1—H1C3	109.5	C15—N5—H5A	118.2
H1C1—C1—H1C3	109.5	C14—C13—H13A	109.5
H1C2—C1—H1C3	109.5	C14—C13—H13B	109.5
O1—C2—N1	122.01 (14)	H13A—C13—H13B	109.5
O1—C2—N2	121.56 (15)	C14—C13—H13C	109.5
N1—C2—N2	116.43 (12)	H13A—C13—H13C	109.5
N2—C3—H3A	109.5	H13B—C13—H13C	109.5
N2—C3—H3B	109.5	N5—C14—C18	117.29 (15)
H3A—C3—H3B	109.5	N5—C14—C13	117.48 (13)
N2—C3—H3C	109.5	C18—C14—C13	125.23 (15)
H3A—C3—H3C	109.5	N5—C15—C16	119.76 (16)
H3B—C3—H3C	109.5	N5—C15—H15	120.1
O3—C4—N2	116.74 (13)	C16—C15—H15	120.1
O3—C4—C5	125.13 (13)	C15—C16—C17	118.83 (17)
N2—C4—C5	118.13 (13)	C15—C16—H16	120.6
C4—C5—C6	120.76 (12)	C17—C16—H16	120.6
C4—C5—C7	119.19 (12)	C16—C17—C18	120.25 (16)
C6—C5—C7	119.92 (12)	C16—C17—H17	119.9
O2—C6—N1	117.79 (13)	C18—C17—H17	119.9
O2—C6—C5	126.04 (13)	C17—C18—C14	120.18 (17)
N1—C6—C5	116.17 (13)	C17—C18—H18	119.9
C12—C7—C8	114.74 (13)	C14—C18—H18	119.9
C12—C7—C5	120.86 (13)

C6—N1—C2—O1	−177.51 (15)	C5—C7—C8—C9	172.31 (14)
C1—N1—C2—O1	1.1 (2)	C12—C7—C8—N3	171.51 (13)
C6—N1—C2—N2	2.3 (2)	C5—C7—C8—N3	−12.2 (2)
C1—N1—C2—N2	−179.10 (15)	O4—N3—C8—C9	134.74 (15)
C4—N2—C2—O1	178.35 (15)	O5—N3—C8—C9	−41.7 (2)
C3—N2—C2—O1	4.1 (2)	O4—N3—C8—C7	−41.1 (2)
C4—N2—C2—N1	−1.5 (2)	O5—N3—C8—C7	142.42 (15)
C3—N2—C2—N1	−175.71 (15)	C7—C8—C9—C10	2.6 (2)
C2—N2—C4—O3	−177.37 (14)	N3—C8—C9—C10	−173.16 (14)
C3—N2—C4—O3	−3.1 (2)	C8—C9—C10—C11	0.6 (2)
C2—N2—C4—C5	1.8 (2)	C8—C9—C10—N4	−178.24 (14)
C3—N2—C4—C5	176.00 (15)	O6—N4—C10—C9	−0.4 (2)
O3—C4—C5—C6	176.28 (14)	O7—N4—C10—C9	179.87 (15)
N2—C4—C5—C6	−2.8 (2)	O6—N4—C10—C11	−179.24 (17)
O3—C4—C5—C7	0.5 (2)	O7—N4—C10—C11	1.0 (2)
N2—C4—C5—C7	−178.55 (12)	C9—C10—C11—C12	−2.1 (2)
C2—N1—C6—O2	177.41 (14)	N4—C10—C11—C12	176.75 (14)
C1—N1—C6—O2	−1.2 (2)	C10—C11—C12—C7	0.5 (2)
C2—N1—C6—C5	−3.3 (2)	C8—C7—C12—C11	2.4 (2)
C1—N1—C6—C5	178.11 (14)	C5—C7—C12—C11	−174.04 (13)
C4—C5—C6—O2	−177.32 (14)	C15—N5—C14—C18	1.4 (2)
C7—C5—C6—O2	−1.6 (2)	C15—N5—C14—C13	−177.90 (16)
C4—C5—C6—N1	3.4 (2)	C14—N5—C15—C16	−0.7 (2)
C7—C5—C6—N1	179.18 (12)	N5—C15—C16—C17	−0.6 (3)
C4—C5—C7—C12	133.84 (15)	C15—C16—C17—C18	1.1 (3)
C6—C5—C7—C12	−41.96 (19)	C16—C17—C18—C14	−0.4 (3)
C4—C5—C7—C8	−42.2 (2)	N5—C14—C18—C17	−0.8 (3)
C6—C5—C7—C8	142.00 (14)	C13—C14—C18—C17	178.41 (18)
C12—C7—C8—C9	−3.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···O3	0.86	1.82	2.6645 (16)	168
C13—H13B···O5ⁱ	0.96	2.42	3.340 (2)	161
C13—H13C···O1ⁱⁱ	0.96	2.42	3.160 (2)	134
C15—H15···O2ⁱⁱⁱ	0.93	2.29	3.021 (2)	135
C16—H16···O6^iv	0.93	2.58	3.323 (2)	138
C17—H17···O1^v	0.93	2.52	3.303 (2)	143

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

Experimental details

Crystal data
Chemical formula	C₆H₈N⁺·C₁₂H₉N₄O₇⁻
M_r	415.37
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	12.8242 (8), 7.0696 (5), 21.5409 (14)
β (°)	101.029 (2)
V (Å³)	1916.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.30 × 0.25 × 0.15

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.917, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	3527, 3527, 2790
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.099, 1.04
No. of reflections	3527
No. of parameters	275
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.17

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···O3	0.86	1.82	2.6645 (16)	168.4
C13—H13B···O5ⁱ	0.96	2.42	3.340 (2)	161.0
C13—H13C···O1ⁱⁱ	0.96	2.42	3.160 (2)	133.5
C15—H15···O2ⁱⁱⁱ	0.93	2.29	3.021 (2)	134.5
C16—H16···O6^iv	0.93	2.58	3.323 (2)	137.7
C17—H17···O1^v	0.93	2.52	3.303 (2)	142.6

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

Acknowledgements

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

References

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