2-Amino-5-bromo-pyridinium hydrogen succinate.

In the title compound, C(5)H(6)BrN(2) (+)·C(4)H(5)O(4) (-), the pyridine N atom of the 2-amino-5-bromo-pyridine mol-ecule is protonated. The protonated N atom and the amino group are linked via N-H⋯O hydrogen bonds to the carboxyl-ate O atoms of the singly deprotonated succinate anion. The hydrogen succinate anions are linked via O-H⋯O hydrogen bonds. A weak inter-molecular C-H⋯O hydrogen bond is also observed.

Related literature

For background to the chemistry of substituted pyridines, see: Pozharski et al. (1997 ▶); Katritzky et al. (1996 ▶). For related structures, see: Goubitz et al. (2001 ▶); Vaday & Foxman (1999 ▶). For applications of succinic acid, see: Sauer et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶). For details of hydrogen bonding, see: Jeffrey & Saenger (1991 ▶); Jeffrey (1997 ▶); Scheiner (1997 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C5H6N2Br+·C4H5O4 −

M = 291.11

Orthorhombic,

a = 5.3275 (2) Å

b = 13.6226 (5) Å

c = 15.1687 (5) Å

V = 1100.86 (7) Å3

Z = 4

Mo Kα radiation

μ = 3.74 mm−1

T = 296 K

0.80 × 0.15 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.155, T max = 0.650

10042 measured reflections

2472 independent reflections

2138 reflections with I > 2s(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.057

S = 0.99

2472 reflections

150 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.31 e Å−3

Absolute structure: Flack (1983 ▶), 995 Friedel pairs

Flack parameter: 0.013 (8)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810006495/is2526sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006495/is2526Isup2.hkl

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

C5H6N2Br+·C4H5O4−	F(000) = 584
Mr = 291.11	Dx = 1.756 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4688 reflections
a = 5.3275 (2) Å	θ = 3.0–26.7°
b = 13.6226 (5) Å	µ = 3.74 mm−1
c = 15.1687 (5) Å	T = 296 K
V = 1100.86 (7) Å3	Needle, yellow
Z = 4	0.80 × 0.15 × 0.13 mm

Bruker SMART APEXII CCD area-detector diffractometer	2472 independent reflections
Radiation source: fine-focus sealed tube	2138 reflections with I > 2s(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→6
Tmin = 0.155, Tmax = 0.650	k = −17→16
10042 measured reflections	l = −19→18

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)] = 0.025	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.057	w = 1/[σ2(Fo2) + (0.0248P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.002
2472 reflections	Δρmax = 0.21 e Å−3
150 parameters	Δρmin = −0.31 e Å−3
0 restraints	Absolute structure: Flack (1983), 995 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.013 (8)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1	0.0791 (3)	0.66915 (12)	0.38303 (10)	0.0490 (4)
O2	0.2588 (3)	0.53970 (10)	0.32236 (11)	0.0441 (4)
O3	0.0528 (4)	0.80559 (14)	0.20813 (14)	0.0633 (6)
O4	−0.3210 (4)	0.86482 (12)	0.24424 (12)	0.0561 (5)
H4	−0.2572	0.9169	0.2290	0.084*
C6	0.0954 (4)	0.60694 (15)	0.32351 (14)	0.0341 (5)
C7	−0.0907 (5)	0.61018 (17)	0.24855 (15)	0.0450 (6)
H7A	−0.1850	0.5493	0.2485	0.054*
H7B	0.0017	0.6134	0.1935	0.054*
C8	−0.2747 (5)	0.69486 (17)	0.25115 (16)	0.0437 (6)
H8A	−0.4068	0.6826	0.2085	0.052*
H8B	−0.3515	0.6971	0.3091	0.052*
C9	−0.1593 (5)	0.79274 (16)	0.23193 (13)	0.0377 (5)
Br1	1.17196 (5)	0.336238 (18)	0.513704 (18)	0.05230 (10)
N1	0.6002 (4)	0.52635 (13)	0.45518 (13)	0.0345 (4)
N2	0.4388 (4)	0.66737 (14)	0.51595 (13)	0.0459 (5)
H2A	0.3300	0.6690	0.4741	0.055*
H2B	0.4388	0.7123	0.5558	0.055*
C1	0.7639 (4)	0.45042 (15)	0.45213 (15)	0.0377 (5)
H1	0.7547	0.4047	0.4067	0.045*
C2	0.9404 (4)	0.44144 (16)	0.51537 (15)	0.0380 (5)
C3	0.9540 (5)	0.51139 (18)	0.58345 (16)	0.0414 (6)
H3	1.0756	0.5056	0.6271	0.050*
C4	0.7899 (5)	0.58693 (16)	0.58521 (14)	0.0405 (5)
H4A	0.7984	0.6332	0.6302	0.049*
C5	0.6060 (4)	0.59588 (15)	0.51909 (14)	0.0343 (5)
H1N1	0.482 (5)	0.5320 (17)	0.4180 (16)	0.047 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0616 (11)	0.0425 (9)	0.0428 (8)	0.0111 (9)	−0.0104 (8)	−0.0157 (8)
O2	0.0495 (10)	0.0309 (8)	0.0520 (9)	0.0067 (7)	−0.0090 (8)	−0.0090 (7)
O3	0.0470 (12)	0.0576 (12)	0.0852 (14)	−0.0024 (9)	0.0118 (11)	0.0229 (10)
O4	0.0603 (11)	0.0347 (9)	0.0733 (12)	0.0024 (10)	0.0199 (11)	0.0111 (8)
C6	0.0412 (13)	0.0265 (10)	0.0347 (11)	−0.0057 (9)	0.0013 (9)	−0.0001 (9)
C7	0.0572 (17)	0.0345 (12)	0.0432 (13)	−0.0017 (11)	−0.0075 (12)	−0.0049 (10)
C8	0.0426 (15)	0.0392 (12)	0.0493 (13)	−0.0033 (10)	−0.0088 (11)	0.0050 (10)
C9	0.0418 (13)	0.0385 (12)	0.0330 (10)	−0.0026 (12)	−0.0029 (12)	0.0039 (9)
Br1	0.04413 (14)	0.04024 (13)	0.07255 (17)	0.00556 (11)	−0.00191 (13)	0.00411 (12)
N1	0.0360 (11)	0.0308 (10)	0.0367 (10)	−0.0035 (8)	−0.0032 (9)	−0.0029 (8)
N2	0.0480 (11)	0.0377 (10)	0.0520 (10)	0.0049 (9)	−0.0099 (10)	−0.0151 (10)
C1	0.0415 (13)	0.0291 (11)	0.0426 (11)	−0.0051 (10)	0.0030 (10)	−0.0034 (9)
C2	0.0364 (12)	0.0334 (11)	0.0442 (11)	−0.0016 (9)	0.0024 (11)	0.0036 (10)
C3	0.0397 (13)	0.0436 (13)	0.0410 (12)	−0.0064 (12)	−0.0046 (11)	0.0035 (11)
C4	0.0443 (14)	0.0411 (12)	0.0362 (11)	−0.0048 (12)	−0.0015 (11)	−0.0057 (10)
C5	0.0355 (11)	0.0303 (10)	0.0370 (10)	−0.0069 (9)	0.0046 (10)	−0.0002 (9)

O1—C6	1.241 (2)	N1—C1	1.354 (3)
O2—C6	1.264 (3)	N1—C5	1.356 (3)
O3—C9	1.199 (3)	N1—H1N1	0.85 (3)
O4—C9	1.319 (3)	N2—C5	1.321 (3)
O4—H4	0.8200	N2—H2A	0.8600
C6—C7	1.509 (3)	N2—H2B	0.8600
C7—C8	1.514 (3)	C1—C2	1.349 (3)
C7—H7A	0.9700	C1—H1	0.9300
C7—H7B	0.9700	C2—C3	1.407 (3)
C8—C9	1.497 (3)	C3—C4	1.351 (3)
C8—H8A	0.9700	C3—H3	0.9300
C8—H8B	0.9700	C4—C5	1.407 (3)
Br1—C2	1.891 (2)	C4—H4A	0.9300
C9—O4—H4	109.5	C1—N1—H1N1	121.6 (17)
O1—C6—O2	123.6 (2)	C5—N1—H1N1	115.4 (17)
O1—C6—C7	118.8 (2)	C5—N2—H2A	120.0
O2—C6—C7	117.60 (18)	C5—N2—H2B	120.0
C6—C7—C8	115.32 (18)	H2A—N2—H2B	120.0
C6—C7—H7A	108.4	C2—C1—N1	119.6 (2)
C8—C7—H7A	108.4	C2—C1—H1	120.2
C6—C7—H7B	108.4	N1—C1—H1	120.2
C8—C7—H7B	108.4	C1—C2—C3	119.8 (2)
H7A—C7—H7B	107.5	C1—C2—Br1	120.93 (17)
C9—C8—C7	114.1 (2)	C3—C2—Br1	119.31 (18)
C9—C8—H8A	108.7	C4—C3—C2	119.8 (2)
C7—C8—H8A	108.7	C4—C3—H3	120.1
C9—C8—H8B	108.7	C2—C3—H3	120.1
C7—C8—H8B	108.7	C3—C4—C5	120.2 (2)
H8A—C8—H8B	107.6	C3—C4—H4A	119.9
O3—C9—O4	123.3 (2)	C5—C4—H4A	119.9
O3—C9—C8	125.1 (2)	N2—C5—N1	118.3 (2)
O4—C9—C8	111.5 (2)	N2—C5—C4	123.99 (19)
C1—N1—C5	122.9 (2)	N1—C5—C4	117.7 (2)
O1—C6—C7—C8	3.3 (3)	C1—C2—C3—C4	0.2 (3)
O2—C6—C7—C8	−177.4 (2)	Br1—C2—C3—C4	179.88 (18)
C6—C7—C8—C9	70.8 (3)	C2—C3—C4—C5	−0.1 (3)
C7—C8—C9—O3	6.8 (3)	C1—N1—C5—N2	179.6 (2)
C7—C8—C9—O4	−173.26 (18)	C1—N1—C5—C4	−0.7 (3)
C5—N1—C1—C2	0.8 (3)	C3—C4—C5—N2	−180.0 (2)
N1—C1—C2—C3	−0.5 (3)	C3—C4—C5—N1	0.4 (3)
N1—C1—C2—Br1	179.82 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2	0.85 (3)	1.88 (3)	2.720 (3)	171 (3)
N2—H2A···O1	0.86	1.92	2.782 (3)	178
N2—H2B···O1i	0.86	2.01	2.805 (3)	154
O4—H4···O2ii	0.82	1.85	2.609 (2)	154
C1—H1···O3iii	0.93	2.43	3.280 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2	0.85 (3)	1.88 (3)	2.720 (3)	171 (3)
N2—H2A⋯O1	0.86	1.92	2.782 (3)	178
N2—H2B⋯O1i	0.86	2.01	2.805 (3)	154
O4—H4⋯O2ii	0.82	1.85	2.609 (2)	154
C1—H1⋯O3iii	0.93	2.43	3.280 (3)	152

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