2-[(E)-(6-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetra-hydro-pyrimidin-5-yl)imino-meth-yl]pyridinium bromide.

The title compound, C(12)H(14)N(5)O(2) (+)·Br(-), is the hydro-bromide salt of a Schiff base in which protonation has taken place at the pyridine N atom. This organic cation is essentially planar (r.m.s. of all fitted non-H atoms = 0.0448 Å). In the crystal, N-H⋯Br hydrogen bonds as well as C-H⋯O and C-H⋯Br inter-actions connect the mol-ecules, forming a three-dimensional network.

Related literature

For the development of radiopharmaceuticals, see: Gerber et al. (2011 ▶). For the crystal structure of the neutral organic parent molecule, see: Booysen et al. (2011a ▶). For the crystal structures of polymorphs of 6-amino-1,3-dimethyl-5-[(E-2-(methyl­sulfan­yl)benzyl­idene­amino]pyrimidine-2,4(1H,3H)-dione, see: Booysen et al. (2011 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C12H14N5O2 +·Br−

M = 340.19

Monoclinic,

a = 8.9520 (2) Å

b = 4.9630 (1) Å

c = 30.9123 (6) Å

β = 105.391 (1)°

V = 1324.14 (5) Å3

Z = 4

Mo Kα radiation

μ = 3.11 mm−1

T = 200 K

0.55 × 0.28 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.660, T max = 1.000

10606 measured reflections

3277 independent reflections

2998 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.068

S = 1.16

3277 reflections

195 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811033290/su2307sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811033290/su2307Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033290/su2307Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536811033290/su2307Isup4.cml

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

C12H14N5O2+·Br−	F(000) = 688
Mr = 340.19	Dx = 1.706 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 7045 reflections
a = 8.9520 (2) Å	θ = 2.7–28.3°
b = 4.9630 (1) Å	µ = 3.11 mm−1
c = 30.9123 (6) Å	T = 200 K
β = 105.391 (1)°	Plate, orange
V = 1324.14 (5) Å3	0.55 × 0.28 × 0.12 mm
Z = 4

Bruker APEXII CCD diffractometer	3277 independent reflections
Radiation source: fine-focus sealed tube	2998 reflections with I > 2σ(I)
graphite	Rint = 0.017
φ and ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
Tmin = 0.660, Tmax = 1.000	k = −6→6
10606 measured reflections	l = −41→38

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ2(Fo2) + (0.0154P)2 + 1.8033P] where P = (Fo2 + 2Fc2)/3
3277 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

	x	y	z	Uiso*/Ueq
O1	1.37652 (19)	0.7382 (4)	0.17215 (6)	0.0318 (4)
O2	1.1136 (2)	0.0840 (3)	0.22406 (5)	0.0308 (4)
N1	1.2019 (2)	0.4910 (4)	0.12052 (6)	0.0207 (4)
N2	1.2433 (2)	0.4126 (4)	0.19775 (6)	0.0231 (4)
N3	0.94690 (19)	−0.0572 (4)	0.13177 (6)	0.0190 (3)
N4	1.0173 (2)	0.2538 (4)	0.06812 (6)	0.0242 (4)
H741	1.053 (3)	0.317 (6)	0.0469 (10)	0.039 (8)*
H742	0.950 (3)	0.138 (6)	0.0608 (9)	0.026 (7)*
N5	0.7294 (2)	−0.4378 (4)	0.09421 (6)	0.0222 (4)
H751	0.763 (3)	−0.333 (6)	0.0774 (9)	0.030 (7)*
C1	1.0559 (2)	0.1427 (4)	0.14542 (6)	0.0189 (4)
C2	1.0908 (2)	0.2922 (4)	0.11067 (7)	0.0188 (4)
C3	1.2809 (2)	0.5581 (4)	0.16435 (7)	0.0226 (4)
C4	1.1344 (2)	0.2018 (4)	0.19125 (7)	0.0212 (4)
C5	1.2294 (3)	0.6593 (5)	0.08419 (8)	0.0292 (5)
H5A	1.2784	0.5504	0.0653	0.044*
H5B	1.2977	0.8096	0.0971	0.044*
H5C	1.1304	0.7298	0.0659	0.044*
C6	1.3189 (3)	0.4895 (6)	0.24431 (8)	0.0354 (6)
H6A	1.4077	0.3709	0.2564	0.053*
H6B	1.2448	0.4724	0.2625	0.053*
H6C	1.3546	0.6766	0.2451	0.053*
C7	0.8975 (2)	−0.2117 (4)	0.15854 (7)	0.0201 (4)
H7	0.9368	−0.1947	0.1901	0.024*
C8	0.7801 (2)	−0.4132 (4)	0.13933 (7)	0.0194 (4)
C9	0.7160 (2)	−0.5808 (4)	0.16555 (7)	0.0235 (4)
H9	0.7485	−0.5673	0.1973	0.028*
C10	0.6044 (3)	−0.7680 (5)	0.14522 (8)	0.0269 (5)
H10	0.5598	−0.8822	0.1631	0.032*
C11	0.5580 (3)	−0.7884 (5)	0.09892 (8)	0.0287 (5)
H11	0.4823	−0.9173	0.0847	0.034*
C12	0.6233 (2)	−0.6188 (5)	0.07375 (7)	0.0269 (5)
H12	0.5930	−0.6304	0.0419	0.032*
Br1	0.75392 (3)	0.85034 (5)	0.004599 (7)	0.03093 (8)

	U11	U22	U33	U12	U13	U23
O1	0.0294 (8)	0.0307 (9)	0.0339 (9)	−0.0127 (7)	0.0057 (7)	−0.0055 (7)
O2	0.0388 (9)	0.0325 (9)	0.0189 (7)	−0.0090 (7)	0.0039 (6)	0.0023 (7)
N1	0.0219 (8)	0.0197 (9)	0.0213 (8)	−0.0046 (7)	0.0073 (7)	−0.0011 (7)
N2	0.0253 (9)	0.0225 (9)	0.0190 (8)	−0.0031 (7)	0.0013 (7)	−0.0029 (7)
N3	0.0189 (8)	0.0183 (8)	0.0200 (8)	−0.0004 (7)	0.0054 (6)	−0.0006 (7)
N4	0.0271 (9)	0.0271 (10)	0.0182 (8)	−0.0072 (8)	0.0056 (7)	0.0012 (7)
N5	0.0228 (8)	0.0245 (9)	0.0197 (8)	−0.0040 (7)	0.0067 (7)	0.0021 (7)
C1	0.0192 (9)	0.0187 (10)	0.0186 (9)	−0.0003 (8)	0.0047 (7)	−0.0009 (8)
C2	0.0185 (9)	0.0171 (10)	0.0207 (9)	0.0012 (7)	0.0052 (7)	−0.0008 (8)
C3	0.0193 (9)	0.0227 (10)	0.0250 (10)	0.0000 (8)	0.0042 (8)	−0.0026 (8)
C4	0.0224 (9)	0.0192 (10)	0.0209 (10)	0.0008 (8)	0.0035 (8)	−0.0008 (8)
C5	0.0359 (12)	0.0257 (11)	0.0290 (11)	−0.0091 (10)	0.0138 (9)	0.0017 (10)
C6	0.0413 (13)	0.0355 (14)	0.0223 (11)	−0.0073 (11)	−0.0038 (10)	−0.0053 (10)
C7	0.0211 (9)	0.0205 (10)	0.0188 (9)	−0.0001 (8)	0.0055 (7)	−0.0003 (8)
C8	0.0194 (9)	0.0199 (10)	0.0192 (9)	0.0012 (8)	0.0055 (7)	0.0002 (8)
C9	0.0254 (10)	0.0245 (11)	0.0213 (10)	−0.0004 (9)	0.0075 (8)	0.0024 (8)
C10	0.0245 (10)	0.0271 (11)	0.0301 (11)	−0.0033 (9)	0.0089 (9)	0.0055 (9)
C11	0.0232 (10)	0.0287 (12)	0.0318 (12)	−0.0068 (9)	0.0030 (9)	0.0010 (9)
C12	0.0246 (10)	0.0310 (12)	0.0223 (10)	−0.0043 (9)	0.0015 (8)	−0.0004 (9)
Br1	0.03684 (13)	0.03914 (14)	0.01623 (10)	−0.01255 (11)	0.00606 (8)	−0.00141 (10)

O1—C3	1.217 (3)	C1—C4	1.435 (3)
O2—C4	1.227 (3)	C5—H5A	0.9800
N1—C2	1.377 (3)	C5—H5B	0.9800
N1—C3	1.392 (3)	C5—H5C	0.9800
N1—C5	1.471 (3)	C6—H6A	0.9800
N2—C3	1.373 (3)	C6—H6B	0.9800
N2—C4	1.407 (3)	C6—H6C	0.9800
N2—C6	1.469 (3)	C7—C8	1.458 (3)
N3—C7	1.290 (3)	C7—H7	0.9500
N3—C1	1.377 (3)	C8—C9	1.387 (3)
N4—C2	1.319 (3)	C9—C10	1.387 (3)
N4—H741	0.87 (3)	C9—H9	0.9500
N4—H742	0.82 (3)	C10—C11	1.384 (3)
N5—C12	1.338 (3)	C10—H10	0.9500
N5—C8	1.353 (3)	C11—C12	1.377 (3)
N5—H751	0.85 (3)	C11—H11	0.9500
C1—C2	1.407 (3)	C12—H12	0.9500
C2—N1—C3	122.47 (17)	N1—C5—H5C	109.5
C2—N1—C5	119.69 (18)	H5A—C5—H5C	109.5
C3—N1—C5	117.56 (18)	H5B—C5—H5C	109.5
C3—N2—C4	125.60 (18)	N2—C6—H6A	109.5
C3—N2—C6	117.31 (19)	N2—C6—H6B	109.5
C4—N2—C6	117.04 (18)	H6A—C6—H6B	109.5
C7—N3—C1	124.61 (18)	N2—C6—H6C	109.5
C2—N4—H741	121 (2)	H6A—C6—H6C	109.5
C2—N4—H742	120.8 (18)	H6B—C6—H6C	109.5
H741—N4—H742	116 (3)	N3—C7—C8	118.67 (18)
C12—N5—C8	123.33 (19)	N3—C7—H7	120.7
C12—N5—H751	116.5 (18)	C8—C7—H7	120.7
C8—N5—H751	120.1 (18)	N5—C8—C9	118.09 (19)
N3—C1—C2	115.38 (17)	N5—C8—C7	119.33 (18)
N3—C1—C4	124.84 (18)	C9—C8—C7	122.58 (19)
C2—C1—C4	119.77 (18)	C10—C9—C8	119.8 (2)
N4—C2—N1	117.62 (19)	C10—C9—H9	120.1
N4—C2—C1	122.17 (19)	C8—C9—H9	120.1
N1—C2—C1	120.19 (18)	C11—C10—C9	120.0 (2)
O1—C3—N2	122.5 (2)	C11—C10—H10	120.0
O1—C3—N1	121.2 (2)	C9—C10—H10	120.0
N2—C3—N1	116.34 (18)	C12—C11—C10	118.9 (2)
O2—C4—N2	119.16 (19)	C12—C11—H11	120.5
O2—C4—C1	125.2 (2)	C10—C11—H11	120.5
N2—C4—C1	115.60 (18)	N5—C12—C11	119.8 (2)
N1—C5—H5A	109.5	N5—C12—H12	120.1
N1—C5—H5B	109.5	C11—C12—H12	120.1
H5A—C5—H5B	109.5
C7—N3—C1—C2	−178.59 (19)	C6—N2—C4—O2	−3.8 (3)
C7—N3—C1—C4	2.4 (3)	C3—N2—C4—C1	−1.3 (3)
C3—N1—C2—N4	176.60 (19)	C6—N2—C4—C1	176.35 (19)
C5—N1—C2—N4	2.8 (3)	N3—C1—C4—O2	−0.7 (3)
C3—N1—C2—C1	−1.7 (3)	C2—C1—C4—O2	−179.7 (2)
C5—N1—C2—C1	−175.54 (19)	N3—C1—C4—N2	179.18 (18)
N3—C1—C2—N4	3.9 (3)	C2—C1—C4—N2	0.2 (3)
C4—C1—C2—N4	−177.0 (2)	C1—N3—C7—C8	179.27 (18)
N3—C1—C2—N1	−177.84 (17)	C12—N5—C8—C9	−1.5 (3)
C4—C1—C2—N1	1.3 (3)	C12—N5—C8—C7	179.3 (2)
C4—N2—C3—O1	−179.9 (2)	N3—C7—C8—N5	1.8 (3)
C6—N2—C3—O1	2.5 (3)	N3—C7—C8—C9	−177.43 (19)
C4—N2—C3—N1	0.9 (3)	N5—C8—C9—C10	0.6 (3)
C6—N2—C3—N1	−176.75 (19)	C7—C8—C9—C10	179.8 (2)
C2—N1—C3—O1	−178.6 (2)	C8—C9—C10—C11	0.4 (3)
C5—N1—C3—O1	−4.7 (3)	C9—C10—C11—C12	−0.6 (4)
C2—N1—C3—N2	0.7 (3)	C8—N5—C12—C11	1.3 (3)
C5—N1—C3—N2	174.62 (19)	C10—C11—C12—N5	−0.2 (4)
C3—N2—C4—O2	178.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H741···Br1i	0.87 (3)	2.77 (3)	3.4584 (19)	138 (2)
N4—H742···Br1ii	0.82 (3)	2.55 (3)	3.312 (2)	154 (2)
N5—H751···Br1ii	0.85 (3)	2.41 (3)	3.1763 (18)	151 (2)
C5—H5A···Br1i	0.98	2.89	3.764 (2)	148.
C6—H6A···O1iii	0.98	2.60	3.453 (3)	145.
C9—H9···O2iv	0.95	2.53	3.446 (3)	162.
C10—H10···O1v	0.95	2.56	3.429 (3)	152.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H741⋯Br1i	0.87 (3)	2.77 (3)	3.4584 (19)	138 (2)
N4—H742⋯Br1ii	0.82 (3)	2.55 (3)	3.312 (2)	154 (2)
N5—H751⋯Br1ii	0.85 (3)	2.41 (3)	3.1763 (18)	151 (2)
C5—H5A⋯Br1i	0.98	2.89	3.764 (2)	148
C6—H6A⋯O1iii	0.98	2.60	3.453 (3)	145
C9—H9⋯O2iv	0.95	2.53	3.446 (3)	162
C10—H10⋯O1v	0.95	2.56	3.429 (3)	152

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