(S)-(−)-6-(4-Bromo­phen­yl)-2,3,5,6-tetra­hydro­thia­zolo[2,3-b]imidazolium hydrogen oxalate

Minor, T.; Chruszcz, M.

doi:10.1107/S1600536808029085

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1954

doi:10.1107/S1600536808029085

Open

access

(S)-(−)-6-(4-Bromophenyl)-2,3,5,6-tetrahydrothiazolo[2,3-b]imidazolium hydrogen oxalate

Thomas Minor ^a and Maksymilian Chruszcz ^a ^*

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

(Received 1 August 2008; accepted 10 September 2008; online 17 September 2008)

The structure of the title compound, C₁₁H₁₂BrN₂S⁺·C₂HO₄⁻ (common name 6-bromolevamisole hydrogen oxalate), is stabilized mainly by hydrogen bonds. Hydrogen oxalate anions form parallel coplanar chains via O—H⋯O hydrogen bonds, while there are N—H⋯O hydrogen-bonding interactions between the 6-bromolevamisole cations and oxalate anions. Both five-membered rings from the 6-bromolevamisole molecule have a twist conformation. The molecule has an extended conformation, with the 4-bromophenyl substituent positioned equatorially with N—C—C—C and C—C—C—C torsion angles of 39.8 (3) and 100.4 (3)°, respectively.

Related literature

For background information, see: Denier et al. (2002 ); Lee et al. (1975 ); Luo et al. (2000 ).

Experimental

Crystal data

C₁₁H₁₂BrN₂S⁺·C₂HO₄⁻
M_r = 373.22
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.615 (1) Å
b = 8.256 (1) Å
c = 32.539 (1) Å
V = 1508.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.88 mm⁻¹
T = 89 (2) K
0.50 × 0.03 × 0.03 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (Otwinowski et al., 2003 ) T_min = 0.90, T_max = 0.92
39658 measured reflections
4061 independent reflections
3438 reflections with I > 2σ(I)
R_int = 0.081

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.074
S = 1.10
4061 reflections
230 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.51 e Å⁻³
Absolute structure: Flack (1983 ), 1863 Friedel pairs
Flack parameter: −0.018 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O3ⁱ	1.03 (5)	1.48 (5)	2.483 (2)	164 (4)
N2—H1N⋯O4	0.83 (4)	1.95 (4)	2.753 (3)	163 (4)
N2—H1N⋯O1	0.83 (4)	2.37 (4)	2.879 (3)	120 (3)
Symmetry code: (i) x-1, y, z.

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, Mercury (Macrae et al., 2006 ), ORTEPIII (Burnett & Johnson, 1996 ) and ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: HKL-3000SM.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808029085/fl2215sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808029085/fl2215Isup2.hkl

checkCIF report

Comment top

6-Bromolevamisole (Fig. 1) is a salt of a strong activator of cystic fibrosis conductance regulator (CTFR) chloride channels, including those in human airway epithelial cells. It shows a strong reduction in activity of Protein Phosphatases 2C and 2A, two of the most likely candidates for being a CTFR phosphatase (Luo et al., 2000). It has also been shown to inhibit alkaline phosphatases, including being an uncompetitive inhibitor of an alkaline phosphatase involved in sarcoma (Lee et al., 1975). Furthermore, since inhibitors affect alkaline phosphatase from the white blood cells of mothers of fetuses with Down's syndrome differently, the cation could be involved in screening for it (Denier et al., 2002).

Packing (Fig. 2) is stabilized by hydrogen bonds (Table 1). The oxalate ions form parallel, coplanar, one-dimensional chains via O—H···O hydrogen bonds, with each link in the chain having an N—H···O hydrogen bond from the deprotonated oxygen to the protonated nitrogen (N2) of the 6-bromolevamisole. The bromine also forms a short contact (3.111 Å) with the O3 (-1/2 + x, 1/2 - y, 2 - z) atom.

Related literature top

For background information, see: Denier et al. (2002); Lee et al. (1975); Luo et al. (2000).

Experimental top

6-Bromolevamisole oxalate was purchased from Sigma, and dissolved in a mixture of 1-butanol and DMSO in a 1:1 ratio. A single crystal suitable for X-ray diffraction study was obtained by slow evaporation at room temperature.

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), HKL-3000SM (Minor et al., 2006); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008), HKL-3000SM (Minor et al., 2006); molecular graphics: HKL-3000SM (Minor et al., 2006), Mercury (Macrae et al., 2006), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: HKL-3000SM (Minor et al., 2006).

Figures top

	Fig. 1. An asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level, while hydrogen atoms are drawn as spheres of an arbitrary radius.
	Fig. 2. A packing diagram with hydrogen bonds marked with blue, dashed lines. Short contacts between Br···O3 (-1/2 + x, 1/2 - y, 2 - z) are marked with red, dashed lines.

(S)-(-)-6-(4-Bromophenyl)-2,3,5,6-tetrahydrothiazolo[2,3- b]imidazolium hydrogen oxalate top

Crystal data top

C₁₁H₁₂BrN₂S⁺·C₂HO₄⁻	D_x = 1.643 Mg m⁻³
M_r = 373.22	Melting point: 465 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71074 Å
Hall symbol: P 2ac 2ab	Cell parameters from 39658 reflections
a = 5.615 (1) Å	θ = 2.6–29.1°
b = 8.256 (1) Å	µ = 2.88 mm⁻¹
c = 32.539 (1) Å	T = 89 K
V = 1508.4 (3) Å³	Needle, colourless
Z = 4	0.50 × 0.03 × 0.03 mm
F(000) = 752

Data collection top

Rigaku R-AXIS RAPID diffractometer	4061 independent reflections
Radiation source: fine-focus sealed tube	3438 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.081
Detector resolution: 10 pixels mm^-1	θ_max = 29.1°, θ_min = 2.6°
ω scans with χ offset	h = −7→7
Absorption correction: multi-scan (Otwinowski et al., 2003)	k = −11→11
T_min = 0.90, T_max = 0.92	l = −44→44
39658 measured reflections

Refinement top

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)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.074	w = 1/[σ²(F_o²) + (0.0326P)² + 0.8007P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.001
4061 reflections	Δρ_max = 0.67 e Å⁻³
230 parameters	Δρ_min = −0.51 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1686 Friedel pairs?
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.018 (7)

Crystal data top

C₁₁H₁₂BrN₂S⁺·C₂HO₄⁻	V = 1508.4 (3) Å³
M_r = 373.22	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.615 (1) Å	µ = 2.88 mm⁻¹
b = 8.256 (1) Å	T = 89 K
c = 32.539 (1) Å	0.50 × 0.03 × 0.03 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	4061 independent reflections
Absorption correction: multi-scan (Otwinowski et al., 2003)	3438 reflections with I > 2σ(I)
T_min = 0.90, T_max = 0.92	R_int = 0.081
39658 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.074	Δρ_max = 0.67 e Å⁻³
S = 1.10	Δρ_min = −0.51 e Å⁻³
4061 reflections	Absolute structure: Flack (1983), 1686 Friedel pairs?
230 parameters	Absolute structure parameter: −0.018 (7)
0 restraints

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.32101 (6)	0.56744 (4)	1.059826 (8)	0.03817 (9)
S1	0.35196 (13)	0.49266 (9)	0.76858 (2)	0.02854 (14)
N2	0.2692 (4)	0.4064 (3)	0.84952 (6)	0.0204 (4)
C11	0.2064 (4)	0.4764 (3)	0.81524 (7)	0.0196 (5)
C7	0.0668 (4)	0.4192 (3)	0.87900 (7)	0.0198 (5)
H7	−0.0267	0.3190	0.8781	0.024*
N1	−0.0024 (4)	0.5521 (3)	0.81664 (6)	0.0201 (4)
C8	−0.0808 (4)	0.5585 (3)	0.85977 (7)	0.0211 (5)
H8A	−0.2505	0.5387	0.8622	0.025*
H8B	−0.0427	0.6620	0.8723	0.025*
C9	−0.0363 (6)	0.6744 (4)	0.78469 (8)	0.0261 (6)
C1	0.1407 (4)	0.4519 (3)	0.92285 (7)	0.0208 (5)
C2	0.3255 (5)	0.5587 (3)	0.93230 (7)	0.0247 (5)
C10	0.0970 (6)	0.6059 (4)	0.74766 (9)	0.0329 (7)
C3	0.3820 (5)	0.5913 (4)	0.97307 (9)	0.0307 (6)
C5	0.0649 (5)	0.4154 (4)	0.99535 (9)	0.0313 (6)
C6	0.0123 (6)	0.3807 (4)	0.95449 (9)	0.0288 (6)
C4	0.2489 (5)	0.5198 (3)	1.00383 (8)	0.0272 (6)
O3	0.8027 (3)	−0.0585 (2)	0.84464 (5)	0.0197 (3)
O4	0.6388 (3)	0.1887 (2)	0.84329 (6)	0.0238 (4)
C1B	0.6295 (4)	0.0378 (3)	0.84479 (7)	0.0172 (5)
C2B	0.3822 (4)	−0.0442 (3)	0.84594 (7)	0.0186 (5)
O1	0.2089 (3)	0.0602 (2)	0.84707 (6)	0.0279 (4)
O2	0.3598 (3)	−0.1898 (2)	0.84549 (7)	0.0320 (5)
H2	0.405 (6)	0.611 (4)	0.9106 (11)	0.040 (10)*
H5	−0.032 (7)	0.372 (5)	1.0134 (12)	0.051 (11)*
H10B	0.158 (8)	0.694 (5)	0.7302 (12)	0.058 (11)*
H9A	−0.201 (7)	0.684 (4)	0.7791 (9)	0.027 (8)*
H3	0.500 (7)	0.655 (4)	0.9791 (10)	0.037 (9)*
H9B	0.031 (6)	0.780 (4)	0.7948 (9)	0.027 (8)*
H10A	0.009 (7)	0.530 (5)	0.7315 (12)	0.052 (11)*
H6	−0.104 (7)	0.305 (5)	0.9487 (10)	0.045 (10)*
H1O	0.042 (9)	0.012 (5)	0.8512 (14)	0.076 (15)*
H1N	0.361 (7)	0.327 (4)	0.8501 (11)	0.044 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0587 (2)	0.03403 (15)	0.02182 (11)	0.00178 (15)	−0.00718 (13)	−0.00204 (11)
S1	0.0306 (3)	0.0314 (3)	0.0237 (3)	0.0028 (3)	0.0062 (3)	−0.0047 (2)
N2	0.0192 (10)	0.0191 (11)	0.0230 (9)	0.0027 (8)	−0.0002 (8)	−0.0023 (8)
C11	0.0207 (11)	0.0133 (12)	0.0248 (11)	−0.0011 (9)	−0.0004 (9)	−0.0053 (8)
C7	0.0188 (11)	0.0176 (12)	0.0230 (11)	0.0011 (10)	0.0009 (9)	−0.0003 (9)
N1	0.0192 (9)	0.0205 (11)	0.0206 (9)	0.0028 (9)	−0.0001 (7)	−0.0001 (8)
C8	0.0186 (11)	0.0235 (12)	0.0212 (10)	0.0031 (11)	0.0009 (8)	0.0011 (10)
C9	0.0315 (16)	0.0259 (14)	0.0209 (12)	0.0032 (12)	−0.0035 (11)	0.0018 (10)
C1	0.0212 (12)	0.0186 (12)	0.0225 (10)	0.0015 (10)	−0.0018 (9)	0.0009 (9)
C2	0.0248 (12)	0.0240 (12)	0.0254 (11)	−0.0056 (12)	0.0014 (10)	−0.0017 (9)
C10	0.0430 (18)	0.0332 (16)	0.0225 (12)	0.0072 (13)	−0.0009 (12)	−0.0022 (11)
C3	0.0328 (16)	0.0310 (16)	0.0282 (13)	−0.0079 (12)	−0.0028 (11)	−0.0046 (11)
C5	0.0358 (15)	0.0316 (16)	0.0263 (12)	−0.0052 (13)	0.0022 (11)	0.0044 (12)
C6	0.0315 (15)	0.0262 (14)	0.0285 (13)	−0.0081 (12)	−0.0030 (11)	0.0025 (11)
C4	0.0369 (14)	0.0251 (13)	0.0195 (11)	0.0047 (11)	−0.0038 (10)	0.0006 (9)
O3	0.0130 (7)	0.0178 (7)	0.0285 (8)	0.0007 (7)	0.0008 (6)	−0.0009 (7)
O4	0.0174 (9)	0.0172 (8)	0.0368 (9)	−0.0001 (7)	−0.0003 (8)	−0.0004 (7)
C1B	0.0153 (10)	0.0211 (13)	0.0153 (9)	0.0003 (9)	0.0006 (8)	−0.0010 (8)
C2B	0.0153 (11)	0.0214 (13)	0.0191 (10)	0.0004 (9)	−0.0011 (8)	−0.0012 (9)
O1	0.0113 (8)	0.0192 (8)	0.0532 (11)	0.0004 (7)	0.0000 (7)	−0.0015 (9)
O2	0.0170 (9)	0.0183 (9)	0.0606 (13)	−0.0004 (7)	0.0001 (9)	−0.0025 (9)

Geometric parameters (Å, º) top

Br1—C4	1.908 (3)	C1—C2	1.396 (4)
S1—C11	1.729 (2)	C2—C3	1.390 (3)
S1—C10	1.840 (3)	C2—H2	0.94 (4)
N2—C11	1.305 (3)	C10—H10B	0.98 (4)
N2—C7	1.491 (3)	C10—H10A	0.96 (4)
N2—H1N	0.83 (4)	C3—C4	1.382 (4)
C11—N1	1.329 (3)	C3—H3	0.87 (4)
C7—C1	1.510 (3)	C5—C4	1.373 (4)
C7—C8	1.549 (3)	C5—C6	1.392 (4)
C7—H7	0.9800	C5—H5	0.88 (4)
N1—C9	1.461 (3)	C6—H6	0.92 (4)
N1—C8	1.472 (3)	O3—C1B	1.257 (3)
C8—H8A	0.9700	O4—C1B	1.248 (3)
C8—H8B	0.9700	C1B—C2B	1.546 (3)
C9—C10	1.527 (4)	C2B—O2	1.208 (3)
C9—H9A	0.95 (4)	C2B—O1	1.300 (3)
C9—H9B	1.00 (3)	O1—H1O	1.03 (5)
C1—C6	1.387 (4)

C11—S1—C10	89.80 (13)	C2—C1—C7	121.7 (2)
C11—N2—C7	108.2 (2)	C3—C2—C1	120.2 (2)
C11—N2—H1N	122 (2)	C3—C2—H2	121 (2)
C7—N2—H1N	121 (3)	C1—C2—H2	118 (2)
N2—C11—N1	114.6 (2)	C9—C10—S1	106.10 (19)
N2—C11—S1	131.1 (2)	C9—C10—H10B	111 (2)
N1—C11—S1	114.23 (18)	S1—C10—H10B	109 (3)
N2—C7—C1	114.3 (2)	C9—C10—H10A	115 (2)
N2—C7—C8	101.55 (19)	S1—C10—H10A	106 (2)
C1—C7—C8	113.3 (2)	H10B—C10—H10A	110 (3)
N2—C7—H7	109.1	C4—C3—C2	119.0 (3)
C1—C7—H7	109.1	C4—C3—H3	121 (2)
C8—C7—H7	109.1	C2—C3—H3	120 (2)
C11—N1—C9	114.5 (2)	C4—C5—C6	118.7 (3)
C11—N1—C8	108.2 (2)	C4—C5—H5	126 (3)
C9—N1—C8	127.9 (2)	C6—C5—H5	115 (3)
N1—C8—C7	101.46 (19)	C1—C6—C5	120.8 (3)
N1—C8—H8A	111.5	C1—C6—H6	120 (2)
C7—C8—H8A	111.5	C5—C6—H6	119 (2)
N1—C8—H8B	111.5	C5—C4—C3	122.0 (3)
C7—C8—H8B	111.5	C5—C4—Br1	118.7 (2)
H8A—C8—H8B	109.3	C3—C4—Br1	119.3 (2)
N1—C9—C10	104.0 (2)	O4—C1B—O3	126.8 (2)
N1—C9—H9A	108.6 (19)	O4—C1B—C2B	118.5 (2)
C10—C9—H9A	110.9 (18)	O3—C1B—C2B	114.69 (19)
N1—C9—H9B	108.4 (17)	O2—C2B—O1	125.6 (2)
C10—C9—H9B	113.1 (18)	O2—C2B—C1B	121.9 (2)
H9A—C9—H9B	111 (3)	O1—C2B—C1B	112.4 (2)
C6—C1—C2	119.3 (2)	C2B—O1—H1O	115 (3)
C6—C1—C7	118.9 (2)

C7—N2—C11—N1	6.2 (3)	N2—C7—C1—C2	39.8 (3)
C7—N2—C11—S1	−175.80 (19)	C8—C7—C1—C2	−75.9 (3)
C10—S1—C11—N2	179.2 (3)	C6—C1—C2—C3	0.9 (4)
C10—S1—C11—N1	−2.8 (2)	C7—C1—C2—C3	177.2 (2)
C11—N2—C7—C1	−141.1 (2)	N1—C9—C10—S1	−32.9 (3)
C11—N2—C7—C8	−18.8 (2)	C11—S1—C10—C9	21.4 (2)
N2—C11—N1—C9	159.8 (2)	C1—C2—C3—C4	−1.6 (4)
S1—C11—N1—C9	−18.5 (3)	C2—C1—C6—C5	0.4 (4)
N2—C11—N1—C8	10.3 (3)	C7—C1—C6—C5	−176.0 (3)
S1—C11—N1—C8	−168.00 (17)	C4—C5—C6—C1	−0.9 (5)
C11—N1—C8—C7	−21.0 (3)	C6—C5—C4—C3	0.2 (4)
C9—N1—C8—C7	−165.2 (2)	C6—C5—C4—Br1	180.0 (2)
N2—C7—C8—N1	23.0 (2)	C2—C3—C4—C5	1.1 (4)
C1—C7—C8—N1	146.1 (2)	C2—C3—C4—Br1	−178.7 (2)
C11—N1—C9—C10	33.8 (3)	O4—C1B—C2B—O2	176.5 (2)
C8—N1—C9—C10	176.1 (2)	O3—C1B—C2B—O2	−2.1 (3)
N2—C7—C1—C6	−143.9 (3)	O4—C1B—C2B—O1	−3.0 (3)
C8—C7—C1—C6	100.4 (3)	O3—C1B—C2B—O1	178.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O3ⁱ	1.03 (5)	1.48 (5)	2.483 (2)	164 (4)
N2—H1N···O4	0.83 (4)	1.95 (4)	2.753 (3)	163 (4)
N2—H1N···O1	0.83 (4)	2.37 (4)	2.879 (3)	120 (3)

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₂BrN₂S⁺·C₂HO₄⁻
M_r	373.22
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	89
a, b, c (Å)	5.615 (1), 8.256 (1), 32.539 (1)
V (Å³)	1508.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.88
Crystal size (mm)	0.50 × 0.03 × 0.03

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (Otwinowski et al., 2003)
T_min, T_max	0.90, 0.92
No. of measured, independent and observed [I > 2σ(I)] reflections	39658, 4061, 3438
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.684

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.074, 1.10
No. of reflections	4061
No. of parameters	230
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.51
Absolute structure	Flack (1983), 1686 Friedel pairs?
Absolute structure parameter	−0.018 (7)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O3ⁱ	1.03 (5)	1.48 (5)	2.483 (2)	164 (4)
N2—H1N···O4	0.83 (4)	1.95 (4)	2.753 (3)	163 (4)
N2—H1N···O1	0.83 (4)	2.37 (4)	2.879 (3)	120 (3)

Symmetry code: (i) x−1, y, z.

Acknowledgements

The authors thank Zbigniew Dauter for helpful discussions. This work was supported by contract No. GI11496 from HKL Research, Inc.

References

Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Denier, C. C., Brisson-Lougarre, A. A., Biasini, G. G., Grozdea, J. J. & Fournier, D. D. (2002). BMC Biochem. 3, 2. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Lee, M. H., Huang, Y. M., Agrawal, C. W. & Sartorelli, A. C. (1975). Biochem. Pharmacol. 24, 1175–1178. PubMed CAS Web of Science Google Scholar
Luo, J. X., Zhu, T., Evagelidis, A., Pato, M. D. & Hanrahan, J. W. (2000). Am. J. Physiol. Cell Physiol. 279, 108–119. Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Minor, W., Cymborowski, M., Otwinowski, Z. & Chruszcz, M. (2006). Acta Cryst. D62, 859–866. Web of Science CrossRef CAS IUCr Journals Google Scholar
Otwinowski, Z., Borek, D., Majewski, W. & Minor, W. (2003). Acta Cryst. A59, 228–234. Web of Science CrossRef CAS IUCr Journals Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1954

doi:10.1107/S1600536808029085

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

(S)-(−)-6-(4-Bromo­phen­yl)-2,3,5,6-tetra­hydro­thia­zolo[2,3-b]imidazolium hydrogen oxalate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(S)-(−)-6-(4-Bromophenyl)-2,3,5,6-tetrahydrothiazolo[2,3-b]imidazolium hydrogen oxalate