2-(Ammonio-meth-yl)pyridinium sulfate monohydrate.

In the crystal of the title hydrated molecular salt, C(6)H(10)N(2) (2+)·SO(4) (2-)·H(2)O, N-H⋯O and O-H⋯O hydrogen bonds link the mol-ecules into layers parallel to the ab plane. C-H⋯O hydrogen bonds are observed both within these layers and between mol-ecules and ions in adjacent layers.

Related literature

For other salts of 2-amino­methyl­pyridine, see: Tooke et al. (2004 ▶); Mahjaub et al. (2005 ▶); Lemmerer et al. (2008 ▶); Khemiri et al. (2010 ▶); Døssing et al. (2001 ▶); Junk et al. (2006 ▶); Yuge et al. (2008 ▶).

Experimental

Crystal data

C6H10N2 2+·SO4 2−·H2O

M = 224.24

Triclinic,

a = 5.2804 (1) Å

b = 6.9458 (2) Å

c = 12.4262 (3) Å

α = 81.392 (1)°

β = 82.874 (1)°

γ = 85.193 (1)°

V = 446.15 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.36 mm−1

T = 100 K

0.35 × 0.34 × 0.23 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.881, T max = 0.921

9334 measured reflections

1926 independent reflections

1846 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.075

S = 1.07

1926 reflections

151 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.49 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812007714/fy2043sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007714/fy2043Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007714/fy2043Isup3.cml

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

C6H10N22+·SO42−·H2O	Z = 2
Mr = 224.24	F(000) = 236
Triclinic, P1	Dx = 1.669 Mg m−3
a = 5.2804 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 6.9458 (2) Å	Cell parameters from 7388 reflections
c = 12.4262 (3) Å	θ = 3.0–28.4°
α = 81.392 (1)°	µ = 0.36 mm−1
β = 82.874 (1)°	T = 100 K
γ = 85.193 (1)°	Cuboid, colourless
V = 446.15 (2) Å3	0.35 × 0.34 × 0.23 mm

Bruker APEXII CCD diffractometer	1846 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 27.0°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −5→6
Tmin = 0.881, Tmax = 0.921	k = −8→8
9334 measured reflections	l = −15→15
1926 independent reflections

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0416P)2 + 0.2718P] where P = (Fo2 + 2Fc2)/3
1926 reflections	(Δ/σ)max = 0.019
151 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.49 e Å−3

Experimental. The intensity data were collected on a Bruker X8 ApexII 4 K Kappa CCD diffractometer using an exposure time of 10 s/frame. A total of 2250 frames were collected with a frame width of 0.5° covering up to θ = 28.43° with 97.3% completeness accomplished.

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
S1	1.22129 (5)	−0.18907 (4)	0.83046 (2)	0.00951 (11)
O4	1.07225 (18)	−0.01241 (13)	0.86655 (8)	0.0137 (2)
O1	1.10127 (19)	−0.36349 (14)	0.89092 (8)	0.0170 (2)
O3	1.2139 (2)	−0.18084 (14)	0.71186 (7)	0.0171 (2)
O2	1.48757 (18)	−0.18785 (16)	0.85337 (8)	0.0206 (2)
N1	0.7557 (2)	0.15757 (15)	0.71789 (9)	0.0113 (2)
C1	0.7793 (3)	0.13486 (19)	0.61148 (11)	0.0144 (3)
H1	0.9219	0.0649	0.5815	0.017*
C2	0.5927 (3)	0.21501 (19)	0.54669 (11)	0.0148 (3)
H2	0.608	0.2008	0.4729	0.018*
C5	0.5565 (2)	0.25896 (18)	0.76561 (10)	0.0106 (2)
C4	0.3629 (2)	0.34100 (18)	0.70404 (10)	0.0121 (3)
H4	0.2225	0.4108	0.7358	0.015*
C3	0.3814 (3)	0.31756 (18)	0.59413 (11)	0.0137 (3)
H3	0.2518	0.3707	0.5522	0.016*
C6	0.5689 (2)	0.27891 (19)	0.88357 (10)	0.0124 (3)
H6A	0.6844	0.1755	0.9149	0.015*
H6B	0.6376	0.4026	0.8875	0.015*
O5	0.8069 (2)	−0.35284 (16)	0.64843 (9)	0.0215 (2)
N2	0.3142 (2)	0.26919 (17)	0.94897 (9)	0.0116 (2)
H9	0.924 (5)	−0.307 (3)	0.6720 (18)	0.034 (6)*
H10	0.682 (5)	−0.305 (3)	0.6830 (19)	0.041 (6)*
H7B	0.235 (3)	0.172 (3)	0.9344 (14)	0.014 (4)*
H7C	0.226 (4)	0.380 (3)	0.9352 (15)	0.023 (4)*
H7A	0.341 (4)	0.246 (3)	1.0179 (17)	0.023 (5)*
H8	0.864 (4)	0.100 (3)	0.7607 (15)	0.021 (4)*

	U11	U22	U33	U12	U13	U23
S1	0.00975 (17)	0.00982 (17)	0.00827 (17)	0.00146 (11)	−0.00037 (11)	−0.00074 (11)
O4	0.0147 (4)	0.0112 (4)	0.0154 (4)	0.0017 (3)	−0.0013 (3)	−0.0048 (3)
O1	0.0185 (5)	0.0109 (4)	0.0181 (5)	0.0016 (4)	0.0055 (4)	0.0017 (4)
O3	0.0247 (5)	0.0183 (5)	0.0090 (5)	−0.0038 (4)	−0.0010 (4)	−0.0035 (4)
O2	0.0097 (5)	0.0313 (6)	0.0186 (5)	0.0013 (4)	−0.0033 (4)	0.0036 (4)
N1	0.0120 (5)	0.0098 (5)	0.0115 (5)	0.0013 (4)	−0.0014 (4)	−0.0009 (4)
C1	0.0165 (6)	0.0132 (6)	0.0128 (6)	−0.0004 (5)	0.0019 (5)	−0.0033 (5)
C2	0.0202 (6)	0.0143 (6)	0.0099 (6)	−0.0041 (5)	−0.0006 (5)	−0.0010 (5)
C5	0.0120 (6)	0.0088 (5)	0.0108 (6)	−0.0019 (4)	0.0005 (4)	−0.0015 (4)
C4	0.0116 (6)	0.0105 (6)	0.0140 (6)	−0.0006 (4)	−0.0008 (5)	−0.0012 (5)
C3	0.0153 (6)	0.0119 (6)	0.0138 (6)	−0.0039 (5)	−0.0042 (5)	0.0019 (5)
C6	0.0108 (6)	0.0154 (6)	0.0112 (6)	0.0005 (4)	−0.0007 (5)	−0.0039 (5)
O5	0.0183 (5)	0.0250 (5)	0.0229 (5)	−0.0029 (4)	−0.0016 (4)	−0.0087 (4)
N2	0.0119 (5)	0.0120 (5)	0.0108 (5)	0.0008 (4)	−0.0003 (4)	−0.0029 (4)

S1—O2	1.4697 (10)	C5—C6	1.5028 (16)
S1—O3	1.4715 (9)	C4—C3	1.3900 (18)
S1—O1	1.4737 (10)	C4—H4	0.93
S1—O4	1.4971 (9)	C3—H3	0.93
N1—C5	1.3419 (16)	C6—N2	1.4835 (16)
N1—C1	1.3443 (17)	C6—H6A	0.97
N1—H8	0.86 (2)	C6—H6B	0.97
C1—C2	1.3783 (19)	O5—H9	0.82 (2)
C1—H1	0.93	O5—H10	0.82 (3)
C2—C3	1.3891 (19)	N2—H7B	0.875 (18)
C2—H2	0.93	N2—H7C	0.87 (2)
C5—C4	1.3860 (17)	N2—H7A	0.87 (2)
O2—S1—O3	109.59 (6)	C5—C4—H4	120.5
O2—S1—O1	110.90 (6)	C3—C4—H4	120.5
O3—S1—O1	110.65 (6)	C2—C3—C4	120.26 (12)
O2—S1—O4	109.13 (6)	C2—C3—H3	119.9
O3—S1—O4	108.33 (6)	C4—C3—H3	119.9
O1—S1—O4	108.17 (5)	N2—C6—C5	112.19 (10)
C5—N1—C1	122.78 (11)	N2—C6—H6A	109.2
C5—N1—H8	116.0 (12)	C5—C6—H6A	109.2
C1—N1—H8	121.1 (12)	N2—C6—H6B	109.2
N1—C1—C2	120.15 (12)	C5—C6—H6B	109.2
N1—C1—H1	119.9	H6A—C6—H6B	107.9
C2—C1—H1	119.9	H9—O5—H10	101 (2)
C1—C2—C3	118.50 (12)	C6—N2—H7B	110.1 (11)
C1—C2—H2	120.8	C6—N2—H7C	109.4 (13)
C3—C2—H2	120.8	H7B—N2—H7C	111.4 (17)
N1—C5—C4	119.20 (11)	C6—N2—H7A	106.9 (12)
N1—C5—C6	115.55 (11)	H7B—N2—H7A	108.3 (16)
C4—C5—C6	125.22 (11)	H7C—N2—H7A	110.7 (17)
C5—C4—C3	119.09 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H7C···O1i	0.87 (2)	2.587 (19)	2.8753 (14)	100.3 (14)
N2—H7A···O2ii	0.87 (2)	1.91 (2)	2.7514 (15)	161.2 (18)
N2—H7B···O4iii	0.875 (18)	1.944 (18)	2.8019 (15)	166.4 (16)
N2—H7C···O1iv	0.87 (2)	1.87 (2)	2.7320 (15)	168.0 (18)
N1—H8···O4	0.86 (2)	1.86 (2)	2.7170 (15)	173.0 (18)
O5—H9···O3	0.82 (2)	1.97 (3)	2.7928 (15)	173 (2)
O5—H10···O2iii	0.82 (3)	2.46 (2)	3.1822 (15)	149 (2)
O5—H10···O3iii	0.82 (3)	2.55 (3)	3.3009 (16)	154 (2)
C2—H2···O3v	0.93	2.39	3.2856 (16)	162
C3—H3···O5vi	0.93	2.57	3.2581 (17)	131
C6—H6A···O4	0.97	2.4	3.2080 (15)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H7C⋯O1i	0.87 (2)	2.587 (19)	2.8753 (14)	100.3 (14)
N2—H7A⋯O2ii	0.87 (2)	1.91 (2)	2.7514 (15)	161.2 (18)
N2—H7B⋯O4iii	0.875 (18)	1.944 (18)	2.8019 (15)	166.4 (16)
N2—H7C⋯O1iv	0.87 (2)	1.87 (2)	2.7320 (15)	168.0 (18)
N1—H8⋯O4	0.86 (2)	1.86 (2)	2.7170 (15)	173.0 (18)
O5—H9⋯O3	0.82 (2)	1.97 (3)	2.7928 (15)	173 (2)
O5—H10⋯O2iii	0.82 (3)	2.46 (2)	3.1822 (15)	149 (2)
O5—H10⋯O3iii	0.82 (3)	2.55 (3)	3.3009 (16)	154 (2)
C2—H2⋯O3v	0.93	2.39	3.2856 (16)	162
C3—H3⋯O5vi	0.93	2.57	3.2581 (17)	131
C6—H6A⋯O4	0.97	2.40	3.2080 (15)	141

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