2-Amino-pyridinium 5-(5-chloro-2,4-dinitro-phen-yl)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetra-hydro-pyrimidin-6-olate.

In the title mol-ecular salt, C(5)H(7)N(2) (+)·C(12)H(8)ClN(4)O(7) (-), the dihedral angle between the aromatic rings of the anion is 51.88 (6)°. One of the nitro groups is disordered over two orientations in a 0.710 (6):0.290 (6) ratio. In the crystal, the cations and anions are linked by N-H⋯O hydrogen bonds, generating infinite ribbons extending along [100] which incorporate R(4) (4)(22) ring motifs. Weak C-H⋯O inter-actions also occur.

Related literature

For our previous work in this area and background to barbiturate drugs, see: Kalaivani & Buvaneswari (2010 ▶); Kalaivani et al. (2008 ▶). For a related structure, see: Swamy et al. (2008 ▶).

Experimental

Crystal data

C5H7N2 +·C12H8ClN4O7 −

M = 450.80

Monoclinic,

a = 8.578 (5) Å

b = 11.229 (5) Å

c = 19.952 (5) Å

β = 94.952 (5)°

V = 1914.7 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.26 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, 2004 ▶) T min = 0.882, T max = 0.941

19182 measured reflections

4053 independent reflections

2996 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.124

S = 1.06

4053 reflections

315 parameters

28 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.25 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., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811049518/hb6510sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049518/hb6510Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811049518/hb6510Isup3.cml

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

C5H7N2+·C12H8ClN4O7−	F(000) = 928
Mr = 450.80	Dx = 1.564 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4951 reflections
a = 8.578 (5) Å	θ = 2.4–25.1°
b = 11.229 (5) Å	µ = 0.26 mm−1
c = 19.952 (5) Å	T = 293 K
β = 94.952 (5)°	Block, colourless
V = 1914.7 (15) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4053 independent reflections
Radiation source: fine-focus sealed tube	2996 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω and φ scan	θmax = 26.7°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→10
Tmin = 0.882, Tmax = 0.941	k = −14→14
19182 measured reflections	l = −18→25

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)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.124	w = 1/[σ2(Fo2) + (0.0563P)2 + 0.6796P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
4053 reflections	Δρmax = 0.38 e Å−3
315 parameters	Δρmin = −0.25 e Å−3
28 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: 0.0051 (11)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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)
Cl1	1.03304 (8)	0.08804 (7)	0.22906 (3)	0.0650 (2)
O1	1.11087 (18)	0.53725 (16)	−0.12650 (8)	0.0532 (6)
O2	1.24783 (16)	0.23068 (14)	0.01566 (8)	0.0460 (5)
O3	0.72232 (15)	0.33672 (15)	−0.03589 (7)	0.0459 (5)
O4	0.7709 (6)	−0.1850 (3)	0.15232 (19)	0.1030 (18)	0.710 (6)
O5	0.7145 (5)	−0.0500 (3)	0.22061 (16)	0.0947 (14)	0.710 (6)
O6	0.8277 (2)	0.09835 (17)	−0.09732 (8)	0.0562 (6)
O7	0.6060 (2)	0.0610 (2)	−0.05967 (10)	0.0784 (8)
N1	0.91735 (19)	0.43435 (15)	−0.08264 (8)	0.0365 (5)
N2	1.17873 (18)	0.38319 (16)	−0.05623 (8)	0.0388 (5)
N3	0.7806 (3)	−0.0840 (2)	0.17169 (11)	0.0648 (9)
N4	0.7452 (2)	0.08402 (17)	−0.05157 (9)	0.0448 (6)
C1	1.0719 (2)	0.4558 (2)	−0.09035 (10)	0.0381 (6)
C2	1.1398 (2)	0.29008 (19)	−0.01345 (10)	0.0365 (6)
C3	0.9800 (2)	0.27172 (18)	−0.00748 (10)	0.0350 (6)
C4	0.8653 (2)	0.34440 (18)	−0.04092 (9)	0.0351 (6)
C5	0.9311 (2)	0.17671 (18)	0.03654 (10)	0.0345 (6)
C6	0.9943 (2)	0.1711 (2)	0.10340 (10)	0.0398 (6)
C7	0.9474 (2)	0.0883 (2)	0.14804 (10)	0.0408 (7)
C8	0.8320 (2)	0.00736 (19)	0.12644 (11)	0.0423 (7)
C9	0.7662 (2)	0.00879 (19)	0.06162 (11)	0.0417 (7)
C10	0.8161 (2)	0.09193 (18)	0.01787 (10)	0.0355 (6)
C11	0.8007 (3)	0.5095 (2)	−0.11964 (11)	0.0456 (7)
C12	1.3446 (2)	0.4019 (2)	−0.06582 (13)	0.0545 (8)
O4'	0.6703 (16)	−0.1204 (15)	0.1656 (8)	0.152 (5)	0.290 (6)
O5'	0.8902 (10)	−0.1336 (8)	0.2104 (5)	0.102 (3)	0.290 (6)
N5	0.6809 (2)	0.31348 (18)	0.17967 (10)	0.0481 (6)
N6	0.5498 (2)	0.2728 (2)	0.07658 (10)	0.0532 (7)
C13	0.5615 (2)	0.2616 (2)	0.14244 (11)	0.0400 (7)
C14	0.4528 (3)	0.1982 (2)	0.17685 (12)	0.0495 (8)
C15	0.4704 (3)	0.1919 (3)	0.24481 (13)	0.0594 (9)
C16	0.5962 (3)	0.2470 (3)	0.28138 (13)	0.0619 (9)
C17	0.6990 (3)	0.3063 (2)	0.24771 (13)	0.0575 (9)
H6	1.07120	0.22570	0.11820	0.0480*
H11B	0.71160	0.46200	−0.13510	0.0680*
H11C	0.84510	0.54440	−0.15760	0.0680*
H12A	1.35390	0.43670	−0.10920	0.0820*
H12B	1.39840	0.32690	−0.06300	0.0820*
H12C	1.39000	0.45440	−0.03150	0.0820*
H9	0.68870	−0.04570	0.04740	0.0500*
H11A	0.76860	0.57140	−0.09060	0.0680*
H5A	0.744 (2)	0.3561 (18)	0.1589 (10)	0.049 (7)*
H6A	0.467 (2)	0.249 (3)	0.0536 (13)	0.073 (9)*
H6B	0.623 (2)	0.302 (2)	0.0556 (12)	0.069 (8)*
H14	0.36870	0.16050	0.15310	0.0590*
H15	0.39740	0.15020	0.26750	0.0710*
H16	0.60800	0.24250	0.32810	0.0740*
H17	0.78410	0.34320	0.27120	0.0690*

	U11	U22	U33	U12	U13	U23
Cl1	0.0728 (4)	0.0825 (5)	0.0377 (3)	−0.0051 (3)	−0.0068 (3)	0.0101 (3)
O1	0.0544 (9)	0.0594 (11)	0.0458 (9)	−0.0187 (8)	0.0043 (7)	0.0157 (8)
O2	0.0325 (7)	0.0504 (9)	0.0544 (9)	−0.0007 (6)	0.0004 (6)	0.0074 (8)
O3	0.0312 (7)	0.0556 (10)	0.0516 (9)	0.0007 (7)	0.0071 (6)	0.0137 (8)
O4	0.186 (4)	0.0408 (19)	0.091 (3)	−0.016 (2)	0.063 (3)	0.0045 (17)
O5	0.149 (3)	0.082 (2)	0.0616 (19)	−0.041 (2)	0.058 (2)	−0.0098 (17)
O6	0.0605 (10)	0.0705 (12)	0.0379 (9)	−0.0008 (8)	0.0061 (7)	−0.0040 (8)
O7	0.0489 (10)	0.1158 (18)	0.0668 (12)	−0.0312 (11)	−0.0159 (8)	0.0137 (12)
N1	0.0365 (8)	0.0383 (10)	0.0345 (9)	−0.0047 (7)	0.0023 (7)	0.0049 (8)
N2	0.0319 (8)	0.0457 (11)	0.0397 (9)	−0.0083 (7)	0.0079 (7)	0.0043 (8)
N3	0.0844 (17)	0.0585 (16)	0.0519 (14)	−0.0244 (13)	0.0078 (12)	0.0123 (12)
N4	0.0436 (10)	0.0453 (11)	0.0443 (10)	−0.0049 (8)	−0.0024 (8)	0.0028 (9)
C1	0.0434 (11)	0.0418 (12)	0.0292 (10)	−0.0116 (9)	0.0035 (8)	−0.0015 (9)
C2	0.0334 (10)	0.0394 (12)	0.0368 (11)	−0.0061 (8)	0.0030 (8)	−0.0013 (9)
C3	0.0322 (10)	0.0380 (11)	0.0347 (10)	−0.0040 (8)	0.0027 (8)	0.0035 (9)
C4	0.0349 (10)	0.0370 (11)	0.0338 (10)	−0.0045 (8)	0.0049 (8)	0.0015 (9)
C5	0.0285 (9)	0.0361 (11)	0.0390 (11)	0.0009 (8)	0.0040 (8)	0.0023 (9)
C6	0.0370 (10)	0.0408 (12)	0.0408 (11)	−0.0062 (9)	−0.0003 (8)	0.0027 (10)
C7	0.0460 (11)	0.0416 (12)	0.0345 (11)	0.0016 (9)	0.0015 (9)	0.0038 (10)
C8	0.0479 (12)	0.0378 (12)	0.0426 (12)	−0.0017 (9)	0.0113 (9)	0.0075 (10)
C9	0.0379 (10)	0.0377 (12)	0.0495 (12)	−0.0060 (9)	0.0047 (9)	0.0010 (10)
C10	0.0330 (9)	0.0382 (11)	0.0349 (10)	−0.0002 (8)	0.0011 (8)	0.0017 (9)
C11	0.0496 (12)	0.0420 (13)	0.0441 (12)	−0.0024 (10)	−0.0028 (9)	0.0092 (10)
C12	0.0361 (11)	0.0690 (17)	0.0598 (15)	−0.0140 (11)	0.0121 (10)	0.0068 (13)
O4'	0.117 (7)	0.166 (9)	0.170 (9)	−0.057 (7)	−0.003 (6)	0.078 (8)
O5'	0.096 (5)	0.092 (6)	0.116 (6)	0.000 (4)	−0.007 (4)	0.078 (5)
N5	0.0361 (9)	0.0528 (12)	0.0555 (12)	−0.0102 (8)	0.0046 (8)	0.0082 (10)
N6	0.0390 (11)	0.0754 (15)	0.0458 (12)	−0.0071 (10)	0.0080 (9)	0.0075 (11)
C13	0.0328 (10)	0.0425 (12)	0.0451 (12)	0.0019 (9)	0.0066 (8)	0.0022 (10)
C14	0.0414 (11)	0.0566 (15)	0.0512 (14)	−0.0118 (10)	0.0081 (10)	−0.0022 (12)
C15	0.0610 (15)	0.0685 (18)	0.0508 (14)	−0.0150 (13)	0.0166 (12)	0.0058 (13)
C16	0.0702 (16)	0.0725 (18)	0.0429 (13)	−0.0057 (14)	0.0048 (12)	0.0003 (13)
C17	0.0535 (14)	0.0628 (17)	0.0542 (15)	−0.0091 (12)	−0.0064 (11)	−0.0014 (13)

Cl1—C7	1.717 (2)	C3—C4	1.402 (3)
O1—C1	1.229 (3)	C3—C5	1.466 (3)
O2—C2	1.244 (3)	C5—C6	1.397 (3)
O3—C4	1.242 (2)	C5—C10	1.398 (3)
O4—N3	1.199 (4)	C6—C7	1.372 (3)
O4'—N3	1.028 (15)	C7—C8	1.385 (3)
O5—N3	1.231 (4)	C8—C9	1.366 (3)
O5'—N3	1.290 (10)	C9—C10	1.372 (3)
O6—N4	1.213 (3)	C6—H6	0.9300
O7—N4	1.219 (3)	C9—H9	0.9300
N1—C4	1.406 (3)	C11—H11C	0.9600
N1—C1	1.369 (3)	C11—H11A	0.9600
N1—C11	1.460 (3)	C11—H11B	0.9600
N2—C12	1.467 (2)	C12—H12A	0.9600
N2—C2	1.408 (3)	C12—H12B	0.9600
N2—C1	1.364 (3)	C12—H12C	0.9600
N3—C8	1.460 (3)	C13—C14	1.399 (3)
N4—C10	1.467 (3)	C14—C15	1.353 (4)
N5—C13	1.345 (3)	C15—C16	1.394 (4)
N5—C17	1.355 (3)	C16—C17	1.332 (4)
N6—C13	1.315 (3)	C14—H14	0.9300
N5—H5A	0.856 (19)	C15—H15	0.9300
N6—H6B	0.85 (2)	C16—H16	0.9300
N6—H6A	0.85 (2)	C17—H17	0.9300
C2—C3	1.401 (3)
C1—N1—C4	123.57 (17)	C6—C7—C8	118.99 (19)
C1—N1—C11	118.01 (17)	N3—C8—C7	121.0 (2)
C4—N1—C11	118.42 (16)	N3—C8—C9	118.15 (19)
C1—N2—C2	124.21 (16)	C7—C8—C9	120.85 (19)
C1—N2—C12	117.82 (17)	C8—C9—C10	118.98 (18)
C2—N2—C12	117.96 (16)	C5—C10—C9	123.07 (19)
O4—N3—O5	121.7 (3)	N4—C10—C5	121.22 (18)
O4—N3—C8	118.8 (3)	N4—C10—C9	115.67 (17)
O5—N3—C8	117.2 (2)	C5—C6—H6	119.00
O4'—N3—C8	122.0 (9)	C7—C6—H6	119.00
O5'—N3—C8	115.5 (4)	C10—C9—H9	121.00
O4'—N3—O5'	121.0 (10)	C8—C9—H9	120.00
O6—N4—O7	123.84 (19)	H11A—C11—H11C	110.00
O6—N4—C10	118.78 (17)	N1—C11—H11A	109.00
O7—N4—C10	117.37 (17)	N1—C11—H11B	109.00
C13—N5—C17	122.9 (2)	H11A—C11—H11B	110.00
C17—N5—H5A	119.7 (13)	H11B—C11—H11C	109.00
C13—N5—H5A	117.3 (13)	N1—C11—H11C	109.00
C13—N6—H6B	122.2 (15)	H12B—C12—H12C	109.00
C13—N6—H6A	119.6 (17)	H12A—C12—H12C	109.00
H6A—N6—H6B	118 (2)	N2—C12—H12A	109.00
O1—C1—N1	120.80 (18)	N2—C12—H12B	109.00
N1—C1—N2	117.01 (18)	N2—C12—H12C	109.00
O1—C1—N2	122.19 (17)	H12A—C12—H12B	109.00
O2—C2—N2	118.36 (16)	N5—C13—C14	117.2 (2)
O2—C2—C3	125.17 (19)	N6—C13—C14	122.84 (19)
N2—C2—C3	116.47 (17)	N5—C13—N6	119.95 (19)
C4—C3—C5	118.91 (16)	C13—C14—C15	119.8 (2)
C2—C3—C4	121.69 (18)	C14—C15—C16	121.0 (3)
C2—C3—C5	119.38 (17)	C15—C16—C17	118.3 (2)
O3—C4—C3	125.33 (18)	N5—C17—C16	120.8 (2)
O3—C4—N1	117.64 (17)	C13—C14—H14	120.00
N1—C4—C3	117.02 (16)	C15—C14—H14	120.00
C3—C5—C10	124.59 (18)	C14—C15—H15	120.00
C6—C5—C10	115.49 (18)	C16—C15—H15	119.00
C3—C5—C6	119.82 (17)	C15—C16—H16	121.00
C5—C6—C7	122.62 (18)	C17—C16—H16	121.00
Cl1—C7—C8	121.88 (17)	N5—C17—H17	120.00
Cl1—C7—C6	119.14 (15)	C16—C17—H17	120.00
C4—N1—C1—O1	−178.55 (19)	O2—C2—C3—C5	0.7 (3)
C11—N1—C1—O1	1.2 (3)	C2—C3—C4—O3	−176.86 (19)
C4—N1—C1—N2	1.4 (3)	C4—C3—C5—C10	50.9 (3)
C11—N1—C1—N2	−178.89 (18)	C2—C3—C5—C10	−131.1 (2)
C1—N1—C4—C3	−1.9 (3)	C4—C3—C5—C6	−125.3 (2)
C11—N1—C4—C3	178.34 (18)	C5—C3—C4—O3	1.1 (3)
C1—N1—C4—O3	177.10 (18)	C2—C3—C5—C6	52.7 (3)
C11—N1—C4—O3	−2.6 (3)	C2—C3—C4—N1	2.1 (3)
C1—N2—C2—O2	−179.13 (19)	C5—C3—C4—N1	−179.97 (18)
C2—N2—C1—N1	−1.0 (3)	C6—C5—C10—N4	−177.07 (17)
C12—N2—C1—N1	177.76 (18)	C3—C5—C10—N4	6.6 (3)
C2—N2—C1—O1	178.9 (2)	C3—C5—C10—C9	−175.78 (18)
C12—N2—C1—O1	−2.3 (3)	C6—C5—C10—C9	0.5 (3)
C12—N2—C2—C3	−177.59 (19)	C10—C5—C6—C7	0.0 (3)
C12—N2—C2—O2	2.2 (3)	C3—C5—C6—C7	176.49 (18)
C1—N2—C2—C3	1.1 (3)	C5—C6—C7—Cl1	179.60 (16)
O5—N3—C8—C9	−116.6 (3)	C5—C6—C7—C8	−0.5 (3)
O4—N3—C8—C9	46.4 (4)	C6—C7—C8—C9	0.5 (3)
O5—N3—C8—C7	65.2 (3)	Cl1—C7—C8—C9	−179.60 (16)
O4—N3—C8—C7	−131.8 (3)	C6—C7—C8—N3	178.68 (19)
O6—N4—C10—C5	38.9 (3)	Cl1—C7—C8—N3	−1.4 (3)
O7—N4—C10—C5	−142.5 (2)	N3—C8—C9—C10	−178.23 (19)
O7—N4—C10—C9	39.8 (3)	C7—C8—C9—C10	0.0 (3)
O6—N4—C10—C9	−138.9 (2)	C8—C9—C10—C5	−0.5 (3)
C13—N5—C17—C16	−0.6 (4)	C8—C9—C10—N4	177.19 (17)
C17—N5—C13—C14	0.1 (3)	N5—C13—C14—C15	0.4 (3)
C17—N5—C13—N6	179.4 (2)	N6—C13—C14—C15	−178.9 (2)
N2—C2—C3—C5	−179.65 (17)	C13—C14—C15—C16	−0.5 (4)
O2—C2—C3—C4	178.6 (2)	C14—C15—C16—C17	0.0 (5)
N2—C2—C3—C4	−1.7 (3)	C15—C16—C17—N5	0.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···O1i	0.856 (19)	1.882 (19)	2.730 (3)	170.8 (19)
N6—H6A···O2ii	0.85 (2)	1.976 (19)	2.805 (3)	163 (3)
N6—H6B···O3	0.85 (2)	2.12 (2)	2.883 (3)	150 (2)
C9—H9···O2iii	0.93	2.51	3.097 (3)	121
C9—H9···O7iv	0.93	2.57	3.285 (3)	134
C11—H11C···O5v	0.96	2.59	3.241 (4)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5A⋯O1i	0.856 (19)	1.882 (19)	2.730 (3)	170.8 (19)
N6—H6A⋯O2ii	0.85 (2)	1.976 (19)	2.805 (3)	163 (3)
N6—H6B⋯O3	0.85 (2)	2.12 (2)	2.883 (3)	150 (2)
C9—H9⋯O2iii	0.93	2.51	3.097 (3)	121
C9—H9⋯O7iv	0.93	2.57	3.285 (3)	134
C11—H11C⋯O5v	0.96	2.59	3.241 (4)	126

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