Redetermination of 2-[4-(2-hydroxy­ethyl)piperazin-1-ium-1-yl]ethanesul­fonate at 100 K

Sledz, P.; Minor, T.; Chruszcz, M.

doi:10.1107/S1600536809042512

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages o3027-o3028

doi:10.1107/S1600536809042512

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Redetermination of 2-[4-(2-hydroxyethyl)piperazin-1-ium-1-yl]ethanesulfonate at 100 K

Pawel Sledz,^a Thomas Minor ^a and Maksymilian Chruszcz ^a ^*

^aUniversity of Virginia, Department of Molecular Physiology & Biological Physics, 1340 Jefferson Park Avenue, Charlottesville, VA 22908, USA
^*Correspondence e-mail: maks@iwonka.med.virginia.edu

(Received 15 September 2009; accepted 15 October 2009; online 7 November 2009)

The crystal structure of the title compound (common name HEPES), C₈H₁₈N₂O₄S, has been redetermined at 100 K in order to properly elucidate the protonation state of the HEPES molecule. The piperazine ring has a chair conformation and one of the N atoms in the ring is protonated, which was not previously reported [Gao, Yin, Yang, & Xue (2004). Acta Cryst. E60, o1328–o1329]. The change of protonation state of the nitrogen atom significantly affects the intermolecular interactions in the HEPES crystal. The structure is stabilized by N—H⋯O and O—H⋯O hydrogen bonds and ionic interactions, as the title compound in solid state is a zwitterion. HEPES molecules pack in layers that are held together by ionic and weak interactions, while a hydrogen-bonded network connects the layers.

Related literature

For background to HEPES and analogous compounds, see: Ferguson et al. (1980 ); Good & Izawa (1972 ); Good et al. (1966 ). For the crystal structure of HEPES crystallized from methanol, see: Wouters et al. (1996 ) and from water, see: Gao et al. (2004 ). For related structures, see: Kubicki et al. (2007 ); Chruszcz et al. (2005 ); Zhao et al. (2006 ).

Experimental

Crystal data

C₈H₁₈N₂O₄S
M_r = 238.31
Orthorhombic, P b c a
a = 8.341 (1) Å
b = 9.567 (1) Å
c = 27.066 (1) Å
V = 2159.8 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 100 K
0.50 × 0.50 × 0.23 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (Otwinowski et al., 2003 ) T_min = 0.86, T_max = 0.93
613697 measured reflections
17694 independent reflections
14854 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.099
S = 1.04
17694 reflections
208 parameters
All H-atom parameters refined
Δρ_max = 0.83 e Å⁻³
Δρ_min = −0.80 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1O4⋯N2ⁱ	0.85 (1)	1.99 (1)	2.8368 (4)	173 (1)
N1—H1N⋯O2ⁱⁱ	0.83 (1)	1.92 (1)	2.7414 (4)	169 (1)
Symmetry codes: (i) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

Data collection: HKL-2000 (Otwinowski & Minor, 1997 ); cell refinement: HKL-2000; data reduction: HKL-2000; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ) and HKL-3000SM (Minor et al., 2006 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and HKL-3000SM; molecular graphics: HKL-3000SM, ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 (Farrugia, 1997 ), Mercury (Macrae et al., 2006 ) and POV-RAY (The POV-RAY Team, 2004 ); software used to prepare material for publication: HKL-3000SM.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809042512/fl2269sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809042512/fl2269Isup2.hkl

checkCIF report

Comment top

The title compound, (I), known commonly as HEPES, is a sulfonic compound used as a zwitterionic buffer. HEPES and analogous compounds (known as the Good buffers) are used during the study of biological processes (Good et al., 1966; Good & Izawa, 1972; Ferguson et al., 1980), and very often during crystallization of macromolecules.

The crystal structures of HEPES crystallized from methanol (determined at 293 K - Wouters et al., 1996) and from water (298 K - Gao et al., 2004) have been already reported. Both previously reported structures crystallized in the Pbca space group, but with different unit-cell parameters. Not only the unit-cell parameters, but also the conformations of the HEPES molecules were different. However, our attention was turned to differences in the reported protonation states of the HEPES molecules. In the structure reported by Wouters et al., the HEPES molecule was presented as zwitterionic (II), while in structure reported by Gao et al. HEPES had both piperazine nitrogen atoms non-protonated and a protonated sulfonic group (III). The non-zwitterionic form of HEPES is quite unusual, as all previously determined structures of compounds from this group, e.g. MES [2-(N-morpholino)ethanesulfonic acid] (Kubicki et al., 2007), MOPS [3-(N-morpholino)propanesulfonic acid] (Chruszcz et al., 2005), PBHPS [piperazine-1,4-diylbis(2-hydroxypropanesulfonic acid)] (Zhao et al., 2006), consistently report zwitterionic forms as being observed in the solid state.

In order to localize all hydrogen atoms, the structure determination was performed at 100 K. The crystal structure of the title compound reported here is isomorphous to the structure reported by Gao et al., but a more detailed analysis revealed that the HEPES molecules are zwitterionic and the nitrogen atom (N1) is protonated (Fig. 1). Change of the localization of the hydrogen atom in comparison with the previously reported structure (Gao et al., 2004) significantly affects the hydrogen bond network (Fig. 2, Table 1), which we believed was previously incorrectly determined. To confirm our finding, we also performed a structural analysis of HEPES crystals (crystallized from water or taken directly from the bottle provided by SIGMA) at 293 K. In both cases (100 K and 293 K) the structures had the same protonation state, which excluded the possibility of temperature dependent changes of protonation.

The differing protonation states reported here and in the structure determined by Wouters et al. suggest that the change in protonation state of the HEPES molecule (and/or the change of the conformations of 2-hydroxyethyl and enthanesulfonic moieties) results in generation of polymorphic forms.

The crystal structure of HEPES is stabilized mainly by hydrogen bonds and ionic interactions. Both nitrogen atoms from the piperazine ring, oxygen atom (O4) from the hydroxyl group and one of the oxygen atom (O2) from the sulfonic group are involved in formation of the hydrogen bond network. Hydrogen bonds extend along the [100] direction and details of their geometric parameters are summarized in Table 1.The HEPES molecules pack in layers that are held together by ionic and weak interactions.

Related literature top

For background to HEPES and analogous compounds, see: Ferguson et al. (1980); Good & Izawa (1972); Good et al. (1966). For the crystal structure of HEPES crystallized from methanol, see: Wouters et al. (1996) and from water, see: Gao et al. (2004). For related structures, see: Kubicki et al. (2007); Chruszcz et al. (2005); Zhao et al. (2006).

Experimental top

HEPES was purchased from SIGMA (99.5% purity, lot 036 K5461). The crystal of (I), used for X-ray diffraction study, was obtained by slow evaporation of HEPES solution in water.

Computing details top

Data collection: HKL-2000 (Otwinowski & Minor, 1997); cell refinement: HKL-2000 (Otwinowski & Minor, 1997); data reduction: HKL-2000 (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) and HKL-3000SM (Minor et al., 2006); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and HKL-3000SM (Minor et al., 2006); molecular graphics: HKL-3000SM (Minor et al., 2006), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 (Farrugia, 1997), Mercury (Macrae et al., 2006) and POV-RAY (The POV-RAY Team, 2004); software used to prepare material for publication: HKL-3000SM (Minor et al., 2006).

Figures top

	Fig. 1. The molecular structures of the title compound. Displacement ellipsoids are drawn at the 75% probability level and hydrogen atoms are drawn as spheres of an arbitrary radius.
	Fig. 2. The molecular packing of compound (I) shown along the [010] axis. Hydrogen atoms are bonds are marked in green, and H-bonds are shown as blue, dashed lines.
	Fig. 3. The structures of (I), (II) and (III).

2-[4-(2-Hydroxyethyl)piperazin-1-ium-1-yl]ethanesulfonate top

Crystal data top

C₈H₁₈N₂O₄S	F(000) = 1024.0
M_r = 238.31	D_x = 1.466 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 613697 reflections
a = 8.341 (1) Å	θ = 2.9–62.9°
b = 9.567 (1) Å	µ = 0.30 mm⁻¹
c = 27.066 (1) Å	T = 100 K
V = 2159.8 (4) Å³	Block, colorless
Z = 8	0.50 × 0.50 × 0.23 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	17694 independent reflections
Radiation source: fine-focus sealed tube	14854 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 10 pixels mm^-1	θ_max = 62.9°, θ_min = 2.9°
ω scan with χ offset	h = −20→20
Absorption correction: multi-scan (Otwinowski et al., 2003)	k = −23→23
T_min = 0.86, T_max = 0.93	l = −67→67
613697 measured reflections

Refinement top

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)] = 0.031	Hydrogen site location: difference Fourier map
wR(F²) = 0.099	All H-atom parameters refined
S = 1.04	w = 1/[σ²(F_o²) + (0.060P)² + 0.0821P] where P = (F_o² + 2F_c²)/3
17694 reflections	(Δ/σ)_max = 0.013
208 parameters	Δρ_max = 0.83 e Å⁻³
0 restraints	Δρ_min = −0.80 e Å⁻³

Crystal data top

C₈H₁₈N₂O₄S	V = 2159.8 (4) Å³
M_r = 238.31	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 8.341 (1) Å	µ = 0.30 mm⁻¹
b = 9.567 (1) Å	T = 100 K
c = 27.066 (1) Å	0.50 × 0.50 × 0.23 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	17694 independent reflections
Absorption correction: multi-scan (Otwinowski et al., 2003)	14854 reflections with I > 2σ(I)
T_min = 0.86, T_max = 0.93	R_int = 0.036
613697 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.099	All H-atom parameters refined
S = 1.04	Δρ_max = 0.83 e Å⁻³
17694 reflections	Δρ_min = −0.80 e Å⁻³
208 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.449764 (8)	0.776637 (6)	0.555875 (2)	0.01145 (1)
N2	0.52317 (2)	0.69925 (2)	0.302785 (7)	0.01111 (2)
O2	0.30713 (2)	0.86815 (2)	0.555768 (7)	0.01413 (3)
N1	0.53191 (2)	0.75196 (2)	0.408697 (7)	0.01121 (2)
O4	0.72742 (3)	0.83527 (2)	0.216353 (8)	0.01514 (3)
C1	0.45506 (3)	0.69919 (3)	0.495798 (9)	0.01321 (3)
C5	0.49778 (3)	0.58710 (2)	0.339211 (8)	0.01316 (3)
O1	0.59735 (3)	0.85596 (3)	0.560910 (9)	0.01744 (3)
C3	0.56026 (3)	0.86534 (2)	0.371519 (9)	0.01330 (3)
C6	0.42540 (3)	0.64240 (2)	0.386736 (8)	0.01298 (3)
C4	0.63131 (3)	0.80396 (2)	0.324618 (8)	0.01271 (3)
C2	0.46765 (3)	0.81142 (3)	0.456032 (9)	0.01364 (3)
C8	0.59941 (3)	0.73733 (3)	0.213505 (9)	0.01485 (3)
C7	0.58957 (3)	0.63743 (2)	0.257306 (8)	0.01343 (3)
O3	0.43278 (4)	0.66097 (3)	0.590283 (9)	0.02055 (4)
H1A	0.5416 (10)	0.6363 (10)	0.4955 (4)	0.030 (2)*
H7B	0.5234 (9)	0.5552 (9)	0.2488 (3)	0.0238 (17)*
H2A	0.5445 (9)	0.8874 (10)	0.4673 (3)	0.0253 (19)*
H4B	0.6453 (10)	0.8784 (8)	0.3001 (3)	0.0252 (16)*
H7A	0.7005 (8)	0.5925 (7)	0.2643 (3)	0.0184 (14)*
H3B	0.4576 (9)	0.9063 (10)	0.3665 (3)	0.0253 (19)*
H6A	0.4173 (11)	0.5721 (9)	0.4086 (3)	0.030 (2)*
H6B	0.3201 (9)	0.6878 (8)	0.3822 (3)	0.0199 (15)*
H4A	0.7367 (10)	0.7630 (8)	0.3328 (3)	0.0193 (15)*
H1O4	0.8138 (12)	0.7897 (9)	0.2127 (3)	0.038 (2)*
H5A	0.6006 (9)	0.5394 (8)	0.3472 (3)	0.0175 (14)*
H3A	0.6309 (10)	0.9315 (7)	0.3860 (3)	0.0217 (16)*
H5B	0.4242 (10)	0.5192 (9)	0.3260 (3)	0.0249 (18)*
H1B	0.3616 (9)	0.6429 (8)	0.4933 (3)	0.0220 (16)*
H8B	0.5045 (10)	0.7906 (9)	0.2102 (3)	0.0225 (17)*
H1N	0.6197 (10)	0.7168 (7)	0.4156 (3)	0.0209 (16)*
H2B	0.3673 (10)	0.8534 (8)	0.4489 (3)	0.0235 (17)*
H8A	0.6076 (9)	0.6844 (8)	0.1846 (3)	0.0193 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01147 (2)	0.01296 (2)	0.00992 (2)	0.00039 (1)	0.00046 (1)	0.00017 (1)
N2	0.01141 (5)	0.01171 (5)	0.01023 (5)	−0.00043 (4)	0.00008 (4)	−0.00049 (4)
O2	0.01144 (6)	0.01507 (5)	0.01589 (6)	0.00088 (4)	0.00135 (4)	−0.00176 (4)
N1	0.01141 (5)	0.01222 (5)	0.01001 (5)	0.00009 (4)	0.00001 (4)	−0.00027 (4)
O4	0.01385 (6)	0.01526 (6)	0.01631 (6)	0.00036 (5)	0.00216 (5)	0.00128 (4)
C1	0.01505 (8)	0.01313 (6)	0.01144 (6)	−0.00002 (5)	0.00161 (5)	−0.00042 (5)
C5	0.01598 (8)	0.01164 (6)	0.01185 (6)	−0.00126 (5)	0.00163 (5)	−0.00039 (4)
O1	0.01166 (6)	0.02271 (8)	0.01794 (7)	−0.00175 (5)	−0.00219 (5)	−0.00297 (6)
C3	0.01666 (8)	0.01192 (6)	0.01131 (6)	−0.00133 (5)	0.00028 (5)	−0.00032 (4)
C6	0.01328 (7)	0.01395 (6)	0.01170 (6)	−0.00217 (5)	0.00141 (5)	−0.00079 (5)
C4	0.01330 (7)	0.01364 (6)	0.01120 (6)	−0.00253 (5)	0.00046 (5)	−0.00035 (5)
C2	0.01686 (8)	0.01329 (6)	0.01078 (6)	0.00146 (6)	0.00107 (5)	−0.00046 (5)
C8	0.01395 (8)	0.01909 (8)	0.01151 (6)	−0.00078 (6)	0.00002 (5)	0.00110 (5)
C7	0.01524 (8)	0.01335 (6)	0.01171 (6)	−0.00001 (5)	0.00150 (5)	−0.00108 (5)
O3	0.03015 (11)	0.01750 (7)	0.01399 (6)	0.00248 (7)	0.00373 (6)	0.00455 (5)

Geometric parameters (Å, º) top

S1—O1	1.4525 (3)	C5—H5A	0.995 (8)
S1—O3	1.4532 (2)	C5—H5B	0.963 (8)
S1—O2	1.4771 (2)	C3—C4	1.5190 (3)
S1—C1	1.7874 (3)	C3—H3B	0.951 (8)
N2—C4	1.4719 (3)	C3—H3A	0.949 (8)
N2—C5	1.4724 (3)	C6—H6A	0.898 (9)
N2—C7	1.4736 (3)	C6—H6B	0.987 (8)
N1—C6	1.4971 (3)	C4—H4B	0.981 (8)
N1—C3	1.4984 (3)	C4—H4A	0.988 (8)
N1—C2	1.5008 (3)	C2—H2A	1.016 (9)
N1—H1N	0.827 (8)	C2—H2B	0.948 (8)
O4—C8	1.4226 (4)	C8—C7	1.5250 (4)
O4—H1O4	0.848 (10)	C8—H8B	0.946 (9)
C1—C2	1.5239 (4)	C8—H8A	0.935 (8)
C1—H1A	0.939 (9)	C7—H7B	0.988 (8)
C1—H1B	0.950 (8)	C7—H7A	1.037 (7)
C5—C6	1.5162 (3)

O1—S1—O3	114.856 (17)	C4—C3—H3A	111.1 (5)
O1—S1—O2	111.907 (17)	H3B—C3—H3A	110.1 (7)
O3—S1—O2	111.966 (15)	N1—C6—C5	110.17 (2)
O1—S1—C1	106.317 (13)	N1—C6—H6A	107.9 (6)
O3—S1—C1	105.650 (15)	C5—C6—H6A	109.1 (6)
O2—S1—C1	105.296 (12)	N1—C6—H6B	105.6 (4)
C4—N2—C5	108.376 (18)	C5—C6—H6B	113.7 (4)
C4—N2—C7	112.22 (2)	H6A—C6—H6B	110.1 (7)
C5—N2—C7	108.719 (19)	N2—C4—C3	111.07 (2)
C6—N1—C3	109.504 (18)	N2—C4—H4B	107.2 (5)
C6—N1—C2	113.10 (2)	C3—C4—H4B	109.3 (5)
C3—N1—C2	110.809 (19)	N2—C4—H4A	111.4 (4)
C6—N1—H1N	109.3 (5)	C3—C4—H4A	108.3 (4)
C3—N1—H1N	107.8 (5)	H4B—C4—H4A	109.5 (6)
C2—N1—H1N	106.1 (5)	N1—C2—C1	111.129 (19)
C8—O4—H1O4	107.0 (6)	N1—C2—H2A	107.6 (5)
C2—C1—S1	110.620 (17)	C1—C2—H2A	109.6 (5)
C2—C1—H1A	113.1 (6)	N1—C2—H2B	107.6 (5)
S1—C1—H1A	106.9 (6)	C1—C2—H2B	112.4 (5)
C2—C1—H1B	113.9 (5)	H2A—C2—H2B	108.4 (7)
S1—C1—H1B	106.2 (5)	O4—C8—C7	114.27 (2)
H1A—C1—H1B	105.5 (8)	O4—C8—H8B	106.2 (5)
N2—C5—C6	111.782 (19)	C7—C8—H8B	111.5 (5)
N2—C5—H5A	110.8 (4)	O4—C8—H8A	110.3 (5)
C6—C5—H5A	108.7 (4)	C7—C8—H8A	108.4 (5)
N2—C5—H5B	109.5 (5)	H8B—C8—H8A	105.8 (7)
C6—C5—H5B	107.3 (5)	N2—C7—C8	114.71 (2)
H5A—C5—H5B	108.7 (7)	N2—C7—H7B	107.7 (5)
N1—C3—C4	110.055 (19)	C8—C7—H7B	110.3 (5)
N1—C3—H3B	104.6 (5)	N2—C7—H7A	110.5 (4)
C4—C3—H3B	113.0 (5)	C8—C7—H7A	110.7 (4)
N1—C3—H3A	107.7 (4)	H7B—C7—H7A	102.1 (5)

O1—S1—C1—C2	−59.26 (2)	C5—N2—C4—C3	−59.66 (2)
O3—S1—C1—C2	178.27 (2)	C7—N2—C4—C3	−179.726 (19)
O2—S1—C1—C2	59.63 (2)	N1—C3—C4—N2	59.63 (3)
C4—N2—C5—C6	59.21 (3)	C6—N1—C2—C1	62.57 (3)
C7—N2—C5—C6	−178.55 (2)	C3—N1—C2—C1	−174.03 (2)
C6—N1—C3—C4	−56.75 (3)	S1—C1—C2—N1	159.105 (18)
C2—N1—C3—C4	177.80 (2)	C4—N2—C7—C8	−68.69 (3)
C3—N1—C6—C5	55.97 (3)	C5—N2—C7—C8	171.44 (2)
C2—N1—C6—C5	−179.911 (19)	O4—C8—C7—N2	76.07 (3)
N2—C5—C6—N1	−58.33 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1O4···N2ⁱ	0.85 (1)	1.99 (1)	2.8368 (4)	173 (1)
N1—H1N···O2ⁱⁱ	0.83 (1)	1.92 (1)	2.7414 (4)	169 (1)

Symmetry codes: (i) x+1/2, y, −z+1/2; (ii) x+1/2, −y+3/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₈H₁₈N₂O₄S
M_r	238.31
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	8.341 (1), 9.567 (1), 27.066 (1)
V (Å³)	2159.8 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.50 × 0.50 × 0.23

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (Otwinowski et al., 2003)
T_min, T_max	0.86, 0.93
No. of measured, independent and observed [I > 2σ(I)] reflections	613697, 17694, 14854
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	1.253

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.099, 1.04
No. of reflections	17694
No. of parameters	208
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.83, −0.80

Computer programs: HKL-2000 (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008) and HKL-3000SM (Minor et al., 2006), SHELXL97 (Sheldrick, 2008) and HKL-3000SM (Minor et al., 2006), HKL-3000SM (Minor et al., 2006), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 (Farrugia, 1997), Mercury (Macrae et al., 2006) and POV-RAY (The POV-RAY Team, 2004), HKL-3000SM (Minor et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1O4···N2ⁱ	0.85 (1)	1.99 (1)	2.8368 (4)	173 (1)
N1—H1N···O2ⁱⁱ	0.83 (1)	1.92 (1)	2.7414 (4)	169 (1)

Symmetry codes: (i) x+1/2, y, −z+1/2; (ii) x+1/2, −y+3/2, −z+1.

Acknowledgements

The authors thank Zbigniew Dauter for helpful discussions. This work was supported by contract GI11496 from HKL Research, Inc.

References

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Volume 65| Part 12| December 2009| Pages o3027-o3028

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Redetermination of 2-[4-(2-hy­droxy­ethyl)piperazin-1-ium-1-yl]ethanesul­fonate at 100 K

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Redetermination of 2-[4-(2-hydroxyethyl)piperazin-1-ium-1-yl]ethanesulfonate at 100 K