2-Methyl-pyridinium 5-(2,4-dinitro-phen-yl)-1,3-dimethyl-barbiturate.

In the title mol-ecular salt [systematic name: 2-methyl-pyridinium 5-(2,4-dinitro-phen-yl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetra-hydro-pyrimidin-4-olate], C(6)H(8)N(+)·C(12)H(9)N(4)O(7) (-), the cation and anion are linked a through strong N-H⋯O hydrogen bond. In the crystal, C-H⋯O inter-actions 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 = 415.37

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.099

S = 1.04

3527 reflections

275 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.17 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812009440/bv2197sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812009440/bv2197Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C6H8N+·C12H9N4O7−	F(000) = 864
Mr = 415.37	Dx = 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

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

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(Fo2) + (0.045P)2 + 0.4365P] where P = (Fo2 + 2Fc2)/3
3527 reflections	(Δ/σ)max < 0.001
275 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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.

	x	y	z	Uiso*/Ueq	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*

	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)

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)

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···O6iv	0.93	2.58	3.323 (2)	138
C17—H17···O1v	0.93	2.52	3.303 (2)	143

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⋯O6iv	0.93	2.58	3.323 (2)	138
C17—H17⋯O1v	0.93	2.52	3.303 (2)	143

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .