2-(2-Pyridylmethyl­ammonio)ethanesulfonate dihydrate

In the crystal structure of the title compound, C₈H₁₂N₂O₃S·2H₂O (HPMT·2H₂O), the organic molecule is a zwitterion. The crystal packing is determined by inter­molecular hydrogen bonds with participation of water mol­ecules, both as donors (O—H...O) and as acceptors (N⁺—H...O).

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.037
• wR factor = 0.099
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

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Computing details

Data collection: APEX-II (Bruker, 2004); cell refinement: APEX-II; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2004); software used to prepare material for publication: SHELXTL.

2-(2-Pyridylmethylammonio)ethanesulfonate dihydrate

Crystal data

C8H12N2O3S·2H2O	F(000) = 536
Mr = 252.29	Dx = 1.419 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1880 reflections
a = 7.810 (6) Å	θ = 2.6–28.1°
b = 5.942 (5) Å	µ = 0.28 mm^−1
c = 25.443 (19) Å	T = 273 K
β = 90.801 (9)°	Lamellar, colourless
V = 1180.7 (15) Å^3	0.39 × 0.23 × 0.22 mm
Z = 4

Data collection

Bruker APEX-II CCD area-detector diffractometer	2125 independent reflections
Radiation source: fine-focus sealed tube	1812 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→4
Tmin = 0.898, Tmax = 0.940	k = −7→7
4345 measured reflections	l = −30→30

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0524P)^2 + 0.3057P] where P = (Fo^2 + 2Fc^2)/3
2125 reflections	(Δ/σ)max = 0.001
161 parameters	Δρmax = 0.27 e Å^−3
6 restraints	Δρmin = −0.46 e Å^−3

Special details

Experimental. IR(KBr,ν,cm-1): 783.3 [γ(C=C—H)], 758.8 (γ CH2); 1200.5, 1171.3, 1056.1 (ν SO3-); 1645.7, 1598.5 (ν C=C+C=N); 3365.3 (ν N—H); 3462.5 (ν O—H)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)

are estimated using the full covariance matrix. The cell e.s.d.'s are taken

into account individually in the estimation of e.s.d.'s in distances, angles

and torsion angles; correlations between e.s.d.'s in cell parameters are only

used when they are defined by crystal symmetry. An approximate (isotropic)

treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.22879 (6)	0.45380 (8)	0.201023 (16)	0.03041 (17)
O1	0.09765 (18)	0.2926 (3)	0.18605 (5)	0.0464 (4)
O2	0.1880 (2)	0.6806 (3)	0.18359 (6)	0.0524 (4)
O3	0.40010 (17)	0.3809 (3)	0.18622 (5)	0.0454 (4)
O4	0.0178 (2)	0.5160 (3)	0.39868 (6)	0.0428 (4)
O5	0.5760 (2)	0.4618 (3)	0.36608 (6)	0.0463 (4)
N1	0.1939 (2)	−0.1546 (3)	0.46052 (6)	0.0358 (4)
N2	0.2620 (2)	0.2476 (3)	0.35343 (5)	0.0295 (4)
H2A	0.3607	0.3169	0.3623	0.035*
H2B	0.1751	0.3318	0.3654	0.035*
C1	0.2571 (2)	0.0320 (3)	0.43838 (7)	0.0295 (4)
C2	0.3178 (3)	0.2117 (4)	0.46797 (8)	0.0404 (5)
H2	0.3609	0.3394	0.4517	0.048*
C3	0.3131 (3)	0.1976 (4)	0.52236 (8)	0.0505 (6)
H3	0.3530	0.3160	0.5431	0.061*
C4	0.2488 (3)	0.0068 (4)	0.54526 (8)	0.0513 (6)
H4	0.2441	−0.0060	0.5816	0.062*
C5	0.1915 (3)	−0.1647 (4)	0.51342 (8)	0.0466 (6)
H5	0.1490	−0.2941	0.5291	0.056*
C6	0.2573 (3)	0.0223 (3)	0.37884 (7)	0.0358 (5)
H6A	0.3559	−0.0637	0.3677	0.043*
H6B	0.1554	−0.0567	0.3668	0.043*
C7	0.2479 (2)	0.2312 (3)	0.29459 (6)	0.0315 (4)
H7A	0.1493	0.1402	0.2849	0.038*
H7B	0.3493	0.1589	0.2809	0.038*
C8	0.2293 (3)	0.4640 (3)	0.27095 (7)	0.0338 (4)
H8A	0.3231	0.5582	0.2832	0.041*
H8B	0.1232	0.5312	0.2827	0.041*
H1W	−0.042 (3)	0.577 (4)	0.3741 (8)	0.095 (11)*
H2W	0.073 (3)	0.612 (4)	0.4173 (9)	0.073 (9)*
H3W	0.583 (3)	0.592 (2)	0.3521 (10)	0.074 (9)*
H4W	0.657 (3)	0.381 (4)	0.3537 (11)	0.093 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0343 (3)	0.0347 (3)	0.0222 (2)	−0.0033 (2)	0.00100 (18)	0.00298 (18)
O1	0.0441 (9)	0.0609 (10)	0.0339 (7)	−0.0181 (7)	−0.0082 (6)	0.0016 (7)
O2	0.0732 (11)	0.0432 (9)	0.0410 (8)	0.0041 (8)	0.0033 (7)	0.0171 (7)
O3	0.0365 (8)	0.0592 (10)	0.0408 (8)	−0.0015 (7)	0.0108 (6)	−0.0063 (7)
O4	0.0487 (10)	0.0407 (9)	0.0389 (8)	0.0032 (7)	−0.0039 (7)	−0.0013 (7)
O5	0.0403 (9)	0.0421 (10)	0.0565 (10)	−0.0064 (8)	0.0053 (7)	0.0005 (8)
N1	0.0399 (10)	0.0376 (10)	0.0301 (8)	0.0002 (8)	0.0030 (7)	0.0067 (7)
N2	0.0317 (9)	0.0333 (9)	0.0233 (7)	−0.0010 (7)	0.0004 (6)	0.0023 (6)
C1	0.0281 (10)	0.0347 (11)	0.0259 (9)	0.0033 (8)	0.0005 (7)	0.0024 (8)
C2	0.0477 (13)	0.0404 (12)	0.0329 (10)	−0.0042 (10)	−0.0046 (9)	0.0024 (9)
C3	0.0635 (16)	0.0543 (14)	0.0333 (11)	0.0077 (12)	−0.0116 (10)	−0.0085 (10)
C4	0.0637 (16)	0.0668 (16)	0.0232 (10)	0.0154 (13)	0.0008 (9)	0.0029 (10)
C5	0.0537 (14)	0.0516 (14)	0.0349 (11)	0.0054 (11)	0.0073 (10)	0.0144 (10)
C6	0.0480 (12)	0.0335 (11)	0.0259 (9)	−0.0026 (9)	0.0023 (8)	0.0034 (8)
C7	0.0372 (11)	0.0359 (11)	0.0213 (8)	−0.0001 (8)	0.0001 (7)	0.0008 (7)
C8	0.0426 (12)	0.0358 (11)	0.0230 (9)	0.0054 (9)	0.0000 (8)	0.0000 (8)

Geometric parameters (Å, º)

S1—O1	1.4492 (16)	C1—C6	1.516 (3)
S1—O2	1.4528 (18)	C2—C3	1.387 (3)
S1—O3	1.4608 (17)	C2—H2	0.9300
S1—C8	1.780 (2)	C3—C4	1.373 (4)
O4—H1W	0.856 (10)	C3—H3	0.9300
O4—H2W	0.855 (10)	C4—C5	1.373 (3)
O5—H3W	0.855 (10)	C4—H4	0.9300
O5—H4W	0.856 (10)	C5—H5	0.9300
N1—C1	1.341 (3)	C6—H6A	0.9700
N1—C5	1.348 (3)	C6—H6B	0.9700
N2—C6	1.487 (3)	C7—C8	1.515 (3)
N2—C7	1.503 (2)	C7—H7A	0.9700
N2—H2A	0.9000	C7—H7B	0.9700
N2—H2B	0.9000	C8—H8A	0.9700
C1—C2	1.386 (3)	C8—H8B	0.9700
O1—S1—O2	112.42 (10)	C5—C4—C3	118.71 (19)
O1—S1—O3	112.51 (11)	C5—C4—H4	120.6
O2—S1—O3	113.22 (10)	C3—C4—H4	120.6
O1—S1—C8	106.07 (9)	N1—C5—C4	123.2 (2)
O2—S1—C8	105.71 (9)	N1—C5—H5	118.4
O3—S1—C8	106.18 (9)	C4—C5—H5	118.4
H1W—O4—H2W	113 (2)	N2—C6—C1	113.63 (15)
H3W—O5—H4W	108 (2)	N2—C6—H6A	108.8
C1—N1—C5	117.80 (18)	C1—C6—H6A	108.8
C6—N2—C7	111.90 (14)	N2—C6—H6B	108.8
C6—N2—H2A	109.2	C1—C6—H6B	108.8
C7—N2—H2A	109.2	H6A—C6—H6B	107.7
C6—N2—H2B	109.2	N2—C7—C8	109.98 (15)
C7—N2—H2B	109.2	N2—C7—H7A	109.7
H2A—N2—H2B	107.9	C8—C7—H7A	109.7
N1—C1—C2	122.28 (17)	N2—C7—H7B	109.7
N1—C1—C6	113.20 (16)	C8—C7—H7B	109.7
C2—C1—C6	124.52 (17)	H7A—C7—H7B	108.2
C1—C2—C3	118.8 (2)	C7—C8—S1	111.38 (13)
C1—C2—H2	120.6	C7—C8—H8A	109.4
C3—C2—H2	120.6	S1—C8—H8A	109.4
C4—C3—C2	119.2 (2)	C7—C8—H8B	109.4
C4—C3—H3	120.4	S1—C8—H8B	109.4
C2—C3—H3	120.4	H8A—C8—H8B	108.0
C5—N1—C1—C2	−0.4 (3)	C7—N2—C6—C1	−175.47 (15)
C5—N1—C1—C6	178.66 (17)	N1—C1—C6—N2	157.93 (17)
N1—C1—C2—C3	0.1 (3)	C2—C1—C6—N2	−23.0 (3)
C6—C1—C2—C3	−178.87 (19)	C6—N2—C7—C8	172.44 (16)
C1—C2—C3—C4	0.0 (3)	N2—C7—C8—S1	175.48 (12)
C2—C3—C4—C5	0.2 (4)	O1—S1—C8—C7	53.16 (17)
C1—N1—C5—C4	0.6 (3)	O2—S1—C8—C7	172.72 (14)
C3—C4—C5—N1	−0.5 (4)	O3—S1—C8—C7	−66.74 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H4W···O2^i	0.86 (1)	1.96 (1)	2.802 (3)	170 (3)
O5—H3W···O3^ii	0.86 (1)	1.98 (1)	2.831 (3)	175 (3)
O4—H2W···N1^iii	0.86 (1)	2.00 (1)	2.852 (3)	178 (3)
O4—H1W···O1^iv	0.86 (1)	2.04 (2)	2.847 (2)	158 (3)
N2—H2B···O4	0.90	1.86	2.751 (3)	171
N2—H2A···O5	0.90	1.89	2.778 (3)	168

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) x, y+1, z; (iv) −x, y+1/2, −z+1/2.