(S)-(-)-6-(4-Bromo-phen-yl)-2,3,5,6-tetra-hydro-thia-zolo[2,3-b]imidazolium hydrogen oxalate.

The structure of the title compound, C(11)H(12)BrN(2)S(+)·C(2)HO(4) (-) (common name 6-bromo-levamisole 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 inter-actions between the 6-bromo-levamisole cations and oxalate anions. Both five-membered rings from the 6-bromo-levamisole mol-ecule have a twist conformation. The mol-ecule has an extended conformation, with the 4-bromo-phenyl 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 = 373.22

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.074

S = 1.10

4061 reflections

230 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.67 e Å−3

Δρmin = −0.51 e Å−3

Absolute structure: Flack (1983 ▶), 1863 Friedel pairs

Flack parameter: −0.018 (7)

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 (n class="Species">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.

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

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

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

C11H12BrN2S+·C2HO4−	Dx = 1.643 Mg m−3
Mr = 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

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

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(Fo2) + (0.0326P)2 + 0.8007P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
4061 reflections	Δρmax = 0.67 e Å−3
230 parameters	Δρmin = −0.51 e Å−3
0 restraints	Absolute structure: Flack (1983), 1686 Friedel pairs?
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.018 (7)

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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)

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) .