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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).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047568/kp2061sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047568/kp2061Isup2.hkl
Contains datablock I

CCDC reference: 630041

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 top

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 top
Crystal data top
C8H12N2O3S·2H2OF(000) = 536
Mr = 252.29Dx = 1.419 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1880 reflections
a = 7.810 (6) Åθ = 2.6–28.1°
b = 5.942 (5) ŵ = 0.28 mm1
c = 25.443 (19) ÅT = 273 K
β = 90.801 (9)°Lamellar, colourless
V = 1180.7 (15) Å30.39 × 0.23 × 0.22 mm
Z = 4
Data collection top
Bruker APEX-II CCD area-detector
diffractometer
2125 independent reflections
Radiation source: fine-focus sealed tube1812 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
φ and ω scansθmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 94
Tmin = 0.898, Tmax = 0.940k = 77
4345 measured reflectionsl = 3030
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0524P)2 + 0.3057P]
where P = (Fo2 + 2Fc2)/3
2125 reflections(Δ/σ)max = 0.001
161 parametersΔρmax = 0.27 e Å3
6 restraintsΔρmin = 0.46 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
S10.22879 (6)0.45380 (8)0.201023 (16)0.03041 (17)
O10.09765 (18)0.2926 (3)0.18605 (5)0.0464 (4)
O20.1880 (2)0.6806 (3)0.18359 (6)0.0524 (4)
O30.40010 (17)0.3809 (3)0.18622 (5)0.0454 (4)
O40.0178 (2)0.5160 (3)0.39868 (6)0.0428 (4)
O50.5760 (2)0.4618 (3)0.36608 (6)0.0463 (4)
N10.1939 (2)0.1546 (3)0.46052 (6)0.0358 (4)
N20.2620 (2)0.2476 (3)0.35343 (5)0.0295 (4)
H2A0.36070.31690.36230.035*
H2B0.17510.33180.36540.035*
C10.2571 (2)0.0320 (3)0.43838 (7)0.0295 (4)
C20.3178 (3)0.2117 (4)0.46797 (8)0.0404 (5)
H20.36090.33940.45170.048*
C30.3131 (3)0.1976 (4)0.52236 (8)0.0505 (6)
H30.35300.31600.54310.061*
C40.2488 (3)0.0068 (4)0.54526 (8)0.0513 (6)
H40.24410.00600.58160.062*
C50.1915 (3)0.1647 (4)0.51342 (8)0.0466 (6)
H50.14900.29410.52910.056*
C60.2573 (3)0.0223 (3)0.37884 (7)0.0358 (5)
H6A0.35590.06370.36770.043*
H6B0.15540.05670.36680.043*
C70.2479 (2)0.2312 (3)0.29459 (6)0.0315 (4)
H7A0.14930.14020.28490.038*
H7B0.34930.15890.28090.038*
C80.2293 (3)0.4640 (3)0.27095 (7)0.0338 (4)
H8A0.32310.55820.28320.041*
H8B0.12320.53120.28270.041*
H1W0.042 (3)0.577 (4)0.3741 (8)0.095 (11)*
H2W0.073 (3)0.612 (4)0.4173 (9)0.073 (9)*
H3W0.583 (3)0.592 (2)0.3521 (10)0.074 (9)*
H4W0.657 (3)0.381 (4)0.3537 (11)0.093 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0343 (3)0.0347 (3)0.0222 (2)0.0033 (2)0.00100 (18)0.00298 (18)
O10.0441 (9)0.0609 (10)0.0339 (7)0.0181 (7)0.0082 (6)0.0016 (7)
O20.0732 (11)0.0432 (9)0.0410 (8)0.0041 (8)0.0033 (7)0.0171 (7)
O30.0365 (8)0.0592 (10)0.0408 (8)0.0015 (7)0.0108 (6)0.0063 (7)
O40.0487 (10)0.0407 (9)0.0389 (8)0.0032 (7)0.0039 (7)0.0013 (7)
O50.0403 (9)0.0421 (10)0.0565 (10)0.0064 (8)0.0053 (7)0.0005 (8)
N10.0399 (10)0.0376 (10)0.0301 (8)0.0002 (8)0.0030 (7)0.0067 (7)
N20.0317 (9)0.0333 (9)0.0233 (7)0.0010 (7)0.0004 (6)0.0023 (6)
C10.0281 (10)0.0347 (11)0.0259 (9)0.0033 (8)0.0005 (7)0.0024 (8)
C20.0477 (13)0.0404 (12)0.0329 (10)0.0042 (10)0.0046 (9)0.0024 (9)
C30.0635 (16)0.0543 (14)0.0333 (11)0.0077 (12)0.0116 (10)0.0085 (10)
C40.0637 (16)0.0668 (16)0.0232 (10)0.0154 (13)0.0008 (9)0.0029 (10)
C50.0537 (14)0.0516 (14)0.0349 (11)0.0054 (11)0.0073 (10)0.0144 (10)
C60.0480 (12)0.0335 (11)0.0259 (9)0.0026 (9)0.0023 (8)0.0034 (8)
C70.0372 (11)0.0359 (11)0.0213 (8)0.0001 (8)0.0001 (7)0.0008 (7)
C80.0426 (12)0.0358 (11)0.0230 (9)0.0054 (9)0.0000 (8)0.0000 (8)
Geometric parameters (Å, º) top
S1—O11.4492 (16)C1—C61.516 (3)
S1—O21.4528 (18)C2—C31.387 (3)
S1—O31.4608 (17)C2—H20.9300
S1—C81.780 (2)C3—C41.373 (4)
O4—H1W0.856 (10)C3—H30.9300
O4—H2W0.855 (10)C4—C51.373 (3)
O5—H3W0.855 (10)C4—H40.9300
O5—H4W0.856 (10)C5—H50.9300
N1—C11.341 (3)C6—H6A0.9700
N1—C51.348 (3)C6—H6B0.9700
N2—C61.487 (3)C7—C81.515 (3)
N2—C71.503 (2)C7—H7A0.9700
N2—H2A0.9000C7—H7B0.9700
N2—H2B0.9000C8—H8A0.9700
C1—C21.386 (3)C8—H8B0.9700
O1—S1—O2112.42 (10)C5—C4—C3118.71 (19)
O1—S1—O3112.51 (11)C5—C4—H4120.6
O2—S1—O3113.22 (10)C3—C4—H4120.6
O1—S1—C8106.07 (9)N1—C5—C4123.2 (2)
O2—S1—C8105.71 (9)N1—C5—H5118.4
O3—S1—C8106.18 (9)C4—C5—H5118.4
H1W—O4—H2W113 (2)N2—C6—C1113.63 (15)
H3W—O5—H4W108 (2)N2—C6—H6A108.8
C1—N1—C5117.80 (18)C1—C6—H6A108.8
C6—N2—C7111.90 (14)N2—C6—H6B108.8
C6—N2—H2A109.2C1—C6—H6B108.8
C7—N2—H2A109.2H6A—C6—H6B107.7
C6—N2—H2B109.2N2—C7—C8109.98 (15)
C7—N2—H2B109.2N2—C7—H7A109.7
H2A—N2—H2B107.9C8—C7—H7A109.7
N1—C1—C2122.28 (17)N2—C7—H7B109.7
N1—C1—C6113.20 (16)C8—C7—H7B109.7
C2—C1—C6124.52 (17)H7A—C7—H7B108.2
C1—C2—C3118.8 (2)C7—C8—S1111.38 (13)
C1—C2—H2120.6C7—C8—H8A109.4
C3—C2—H2120.6S1—C8—H8A109.4
C4—C3—C2119.2 (2)C7—C8—H8B109.4
C4—C3—H3120.4S1—C8—H8B109.4
C2—C3—H3120.4H8A—C8—H8B108.0
C5—N1—C1—C20.4 (3)C7—N2—C6—C1175.47 (15)
C5—N1—C1—C6178.66 (17)N1—C1—C6—N2157.93 (17)
N1—C1—C2—C30.1 (3)C2—C1—C6—N223.0 (3)
C6—C1—C2—C3178.87 (19)C6—N2—C7—C8172.44 (16)
C1—C2—C3—C40.0 (3)N2—C7—C8—S1175.48 (12)
C2—C3—C4—C50.2 (4)O1—S1—C8—C753.16 (17)
C1—N1—C5—C40.6 (3)O2—S1—C8—C7172.72 (14)
C3—C4—C5—N10.5 (4)O3—S1—C8—C766.74 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H4W···O2i0.86 (1)1.96 (1)2.802 (3)170 (3)
O5—H3W···O3ii0.86 (1)1.98 (1)2.831 (3)175 (3)
O4—H2W···N1iii0.86 (1)2.00 (1)2.852 (3)178 (3)
O4—H1W···O1iv0.86 (1)2.04 (2)2.847 (2)158 (3)
N2—H2B···O40.901.862.751 (3)171
N2—H2A···O50.901.892.778 (3)168
Symmetry codes: (i) x+1, y1/2, 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.
 

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