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Acta Cryst. (2007). E63, o2433
https://doi.org/10.1107/S160053680701673X
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2-[(2-Furylmeth­yl)sulfan­yl]-1H-3,1-benzimidazol-3-ium chloride dihydrate

S. Ö. Yildirim, M. Akkurt, N. Sireci, H. Küçükbay and C. Kazak
The title compound, C12H11N2OS+·Cl-·2H2O, was synthesized from the potassium salt of 2-mercaptobenzimidazole and 2-chloro­methyl­furan in ethanol. The mol­ecule is not planar; the dihedral angle between the benzimidazole and furan ring systems is 83.2 (1)°. Cations, anions, and water molecules are extensively connected by hydrogen bonds.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680701673X/bt2335sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680701673X/bt2335Isup2.hkl
Contains datablock I

CCDC reference: 647569

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.036
  • wR factor = 0.093
  • Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found






Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C11    -   C12     ..       5.67 su
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              H2 O


   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

In the molecule of (I) (Fig. 1), the C—N bond lengths (Table 1) in the benzimidazole ring system confirm the delocalization of the π electrons in this system. The title molecule is composed of a five-membered ring and a nine-membered bicyclic system linked by a thio and methylene group. The nine-membered benzimidazole ring and the five-membered furan ring (Fig. 1) are planar. The molecule, on the other hand, is not planar; the dihedral angle between the two ring systems is 83.2 (1)°. Geometric parameters are as expected (Table 1) and agree well with those reported for other structures (Akkurt et al., 2004; Akkurt et al., 2005; Akkurt, Türktekin et al., 2006; Akkurt, Yıldırım et al., 2006; Yıldırım et al., 2005).

In the crystal structure, there are N—H···O, N—H···Cl, O—H···Cl, O—H···O and C—H···Cl intra- and intermolecular hydrogen bonds (Table 2) (Fig. 2).

Related literature top

The crystal structures of some related benzimidazole derivatives have previously reported (Akkurt et al., 2004; Akkurt et al., 2005; Akkurt, Türktekin et al., 2006; Akkurt, Yıldırım et al., 2006; Yıldırım et al., 2005).

Experimental top

A mixture of potassium salt of 2-mercaptobenzimidazole (1.0 g; 5.3 mmol) and 2-chloromethylfuran (0.65 g; 5.3 mmol) in ethanol (25 ml) was heated under reflux for 5 h. The mixture was cooled to room temperature and potassium chloride was then filtered off and washed a little EtOH. All volatiles were removed in vacuo (0.02 m mH g; 1 m mH g = 133.322 Pa) and HCl was added to convertsalt form before crystallization of crude product from EtOH. (yield:1.2 g, 75%;m.p. 424–425 (dec)K. 1H-NMR (DMSO-d6, p.p.m.): 4.96 (s, –S—CH2–, 2H),6.36 (t, furan-H, 1H), 6.50 (d, furan-H,1H),7.44 (t, Ar—H, 2H), 7.48 (s, –NH–, 1H), 7.67 (s, =NH–, 1H), 7.71 (m, Ar—H, 2H). 13C-NMR (CDCl3): δ 29.89, 107.30, 110.07, 113.77, 114.90, 125.59, 126.55, 130.86, 133.37, 144.16, 149.25. Analytical calculated for C12H15N2SO3Cl: C 47.60, H 4.95, N 9.25, S 10.57%. Found: C 47.25, H 4.95, N 9.06, S 11.07%.

Refinement top

The H atoms of the water molecules were found from a difference Fourier map and refined freely. The other H atoms were geometrically positioned with Caromatic–H = 0.93 Cmethylene–H = 0.97Å and N–H = 0.86 Å, and with Uiso(H) = 1.2Ueq(C,N).

Structure description top

In the molecule of (I) (Fig. 1), the C—N bond lengths (Table 1) in the benzimidazole ring system confirm the delocalization of the π electrons in this system. The title molecule is composed of a five-membered ring and a nine-membered bicyclic system linked by a thio and methylene group. The nine-membered benzimidazole ring and the five-membered furan ring (Fig. 1) are planar. The molecule, on the other hand, is not planar; the dihedral angle between the two ring systems is 83.2 (1)°. Geometric parameters are as expected (Table 1) and agree well with those reported for other structures (Akkurt et al., 2004; Akkurt et al., 2005; Akkurt, Türktekin et al., 2006; Akkurt, Yıldırım et al., 2006; Yıldırım et al., 2005).

In the crystal structure, there are N—H···O, N—H···Cl, O—H···Cl, O—H···O and C—H···Cl intra- and intermolecular hydrogen bonds (Table 2) (Fig. 2).

The crystal structures of some related benzimidazole derivatives have previously reported (Akkurt et al., 2004; Akkurt et al., 2005; Akkurt, Türktekin et al., 2006; Akkurt, Yıldırım et al., 2006; Yıldırım et al., 2005).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. An ORTEP-3 view of (I), with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
[Figure 2] Fig. 2. A view of the crystal packing of (I), looking down the a axis; H atoms not involved in hydrogen bonds omitted; dashed lines indicate hydrogen contacts.
2-[(2-furylmethyl)sulfanyl]-1H-3,1-benzimidazol-3-ium chloride dihydrate top
Crystal data top
C12H11N2OS+·Cl−·2H2OF(000) = 632
Mr = 302.78Dx = 1.393 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 12416 reflections
a = 7.0649 (6) Åθ = 1.9–27.1°
b = 21.5994 (17) ŵ = 0.41 mm−1
c = 9.5520 (7) ÅT = 296 K
β = 97.925 (6)°Prism, colourless
V = 1443.7 (2) Å30.51 × 0.42 × 0.32 mm
Z = 4
Data collection top
Stoe IPDS2
diffractometer		3158 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus1882 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.045
Detector resolution: 6.67 pixels mm-1θmax = 27.1°, θmin = 1.9°
ω scansh = −9→9
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		k = −27→27
Tmin = 0.817, Tmax = 0.879l = −12→12
12197 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.093 w = 1/[σ2(Fo2) + (0.0559P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.84(Δ/σ)max < 0.001
3158 reflectionsΔρmax = 0.19 e Å−3
189 parametersΔρmin = −0.25 e Å−3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0078 (13)
Crystal data top
C12H11N2OS+·Cl−·2H2OV = 1443.7 (2) Å3
Mr = 302.78Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.0649 (6) ŵ = 0.41 mm−1
b = 21.5994 (17) ÅT = 296 K
c = 9.5520 (7) Å0.51 × 0.42 × 0.32 mm
β = 97.925 (6)°
Data collection top
Stoe IPDS2
diffractometer		3158 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		1882 reflections with I > 2σ(I)
Tmin = 0.817, Tmax = 0.879Rint = 0.045
12197 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.093H atoms treated by a mixture of independent and constrained refinement
S = 0.84Δρmax = 0.19 e Å−3
3158 reflectionsΔρmin = −0.25 e Å−3
189 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
S10.28109 (10)0.18243 (3)0.44205 (7)0.0676 (2)
O1−0.0559 (2)0.26590 (7)0.57648 (17)0.0666 (6)
N10.2396 (2)0.05992 (7)0.41089 (17)0.0508 (6)
N20.3027 (2)0.08569 (7)0.63196 (17)0.0499 (5)
C10.2474 (3)0.00497 (9)0.4873 (2)0.0463 (6)
C20.2215 (3)−0.05649 (10)0.4465 (2)0.0563 (8)
C30.2386 (3)−0.09954 (10)0.5533 (3)0.0616 (8)
C40.2792 (3)−0.08243 (10)0.6947 (2)0.0649 (9)
C50.3050 (3)−0.02185 (10)0.7354 (2)0.0578 (8)
C60.2875 (3)0.02143 (9)0.6287 (2)0.0455 (6)
C70.2740 (3)0.10729 (9)0.4996 (2)0.0494 (7)
C80.2646 (3)0.22625 (9)0.6037 (2)0.0573 (8)
C90.0741 (3)0.22686 (8)0.6481 (2)0.0480 (6)
C10−0.0055 (3)0.19611 (10)0.7456 (2)0.0545 (7)
C11−0.1959 (3)0.21770 (11)0.7380 (2)0.0630 (8)
C12−0.2199 (3)0.25924 (11)0.6361 (3)0.0681 (9)
O2−0.1594 (3)0.06471 (12)0.9334 (2)0.0775 (8)
O30.1745 (3)0.06500 (8)1.12185 (18)0.0678 (6)
Cl10.44294 (7)0.13331 (2)0.93504 (6)0.0562 (2)
H10.216200.062800.320400.0610*
H20.19410−0.067900.352000.0680*
H2A0.326800.107900.707000.0600*
H30.22270−0.141300.530500.0740*
H40.28910−0.113100.763700.0780*
H50.33270−0.010600.830000.0690*
H8A0.354300.208900.679500.0690*
H8B0.303300.268600.589600.0690*
H100.052800.166200.807000.0650*
H11−0.286500.205000.794000.0760*
H12−0.332500.281000.608700.0820*
H21−0.274 (6)0.0857 (18)0.937 (4)0.152 (15)*
H22−0.182 (6)0.0299 (19)0.929 (4)0.138 (18)*
H310.252 (4)0.0849 (12)1.082 (3)0.084 (9)*
H320.055 (6)0.073 (2)1.070 (5)0.176 (18)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0905 (5)0.0574 (3)0.0611 (4)0.0132 (3)0.0330 (3)0.0147 (3)
O10.0700 (10)0.0607 (9)0.0695 (11)0.0096 (8)0.0112 (8)0.0167 (8)
N10.0570 (10)0.0601 (10)0.0360 (9)0.0062 (8)0.0094 (7)0.0019 (8)
N20.0623 (10)0.0496 (9)0.0387 (9)0.0012 (8)0.0104 (8)−0.0020 (7)
C10.0454 (10)0.0544 (11)0.0401 (11)0.0048 (9)0.0090 (8)0.0007 (9)
C20.0559 (13)0.0628 (13)0.0508 (13)−0.0004 (10)0.0091 (10)−0.0120 (10)
C30.0666 (14)0.0517 (12)0.0667 (16)−0.0010 (10)0.0103 (11)−0.0067 (11)
C40.0845 (17)0.0529 (12)0.0575 (15)0.0010 (11)0.0107 (12)0.0077 (11)
C50.0730 (15)0.0573 (12)0.0430 (12)0.0007 (10)0.0081 (10)0.0039 (9)
C60.0488 (11)0.0464 (10)0.0421 (11)0.0023 (8)0.0092 (8)−0.0008 (8)
C70.0515 (12)0.0556 (11)0.0430 (12)0.0068 (9)0.0137 (9)0.0049 (9)
C80.0591 (13)0.0468 (11)0.0677 (15)−0.0030 (9)0.0152 (11)0.0052 (10)
C90.0534 (11)0.0415 (10)0.0487 (12)0.0012 (9)0.0053 (9)−0.0025 (9)
C100.0541 (12)0.0555 (12)0.0535 (13)0.0005 (9)0.0057 (10)0.0112 (10)
C110.0580 (13)0.0800 (16)0.0527 (13)−0.0050 (12)0.0136 (10)0.0011 (12)
C120.0545 (14)0.0699 (14)0.0804 (18)0.0128 (11)0.0107 (12)−0.0016 (13)
O20.0754 (13)0.0817 (14)0.0744 (13)0.0137 (11)0.0066 (9)0.0059 (10)
O30.0687 (11)0.0866 (12)0.0487 (10)−0.0051 (9)0.0100 (8)0.0097 (8)
Cl10.0560 (3)0.0628 (3)0.0493 (3)−0.0030 (2)0.0055 (2)−0.0033 (2)
Geometric parameters (Å, º) top
S1—C71.717 (2)C3—C41.392 (3)
S1—C81.828 (2)C4—C51.370 (3)
O1—C91.360 (2)C5—C61.376 (3)
O1—C121.367 (3)C8—C91.466 (3)
O2—H210.93 (4)C9—C101.330 (3)
O2—H220.77 (4)C10—C111.416 (3)
O3—H310.83 (3)C11—C121.318 (3)
O3—H320.93 (4)C2—H20.9300
N1—C71.329 (2)C3—H30.9300
N1—C11.391 (2)C4—H40.9300
N2—C61.392 (2)C5—H50.9300
N2—C71.337 (2)C8—H8A0.9700
N1—H10.8600C8—H8B0.9700
N2—H2A0.8600C10—H100.9300
C1—C61.388 (3)C11—H110.9300
C1—C21.389 (3)C12—H120.9300
C2—C31.373 (3)
Cl1···N23.1032 (17)C10···H3viii3.1000
Cl1···O2i3.178 (2)C10···H2A3.0800
Cl1···O33.145 (2)C11···H3viii3.0300
Cl1···H11i2.9300C12···H3viii3.0000
Cl1···H2A2.2900C12···H4xi2.9800
Cl1···H8A2.9300H1···O3ix1.8800
Cl1···H102.9400H1···H31ix2.3700
Cl1···H8Bii2.8400H1···H32ix2.5100
Cl1···H21i2.25 (4)H2···O2viii2.7000
Cl1···H312.33 (3)H2A···Cl12.2900
Cl1···H12iii2.8200H2A···H8A2.2100
S1···O13.3780 (17)H2A···H102.6000
S1···C9iv3.568 (2)H2A···C82.7500
S1···C10iv3.668 (2)H2A···C103.0800
O1···C10iv3.332 (3)H3···C10viii3.1000
O1···S13.3780 (17)H3···C12viii3.0000
O1···C11iv3.267 (3)H3···C11viii3.0300
O2···Cl1v3.178 (2)H4···H12xii2.5900
O2···O3vi2.850 (3)H4···C12xii2.9800
O2···O32.763 (3)H8A···N22.7200
O3···O2vi2.850 (3)H8A···Cl12.9300
O3···Cl13.145 (2)H8A···H2A2.2100
O3···N1vii2.738 (2)H8B···H12i2.5700
O3···O22.763 (3)H8B···Cl1iv2.8400
O2···H321.87 (5)H10···Cl12.9400
O2···H2viii2.7000H10···H2A2.6000
O3···H22vi2.11 (4)H11···Cl1v2.9300
O3···H1vii1.8800H12···C8v3.0800
N1···O3ix2.738 (2)H12···Cl1xiii2.8200
N1···N22.170 (2)H12···H8Bv2.5700
N2···N12.170 (2)H12···H4xi2.5900
N2···Cl13.1032 (17)H21···H322.51 (6)
N2···H8A2.7200H21···Cl1v2.25 (4)
C1···C1x3.550 (3)H22···O3vi2.11 (4)
C1···C1viii3.544 (3)H22···H32vi2.40 (6)
C3···C7x3.553 (3)H22···H31vi2.53 (5)
C3···C7viii3.591 (3)H22···H322.21 (6)
C7···C3viii3.591 (3)H31···H22vi2.53 (5)
C7···C3x3.553 (3)H31···Cl12.33 (3)
C9···S1ii3.568 (2)H31···H1vii2.3700
C10···O1ii3.332 (3)H32···H1vii2.5100
C10···S1ii3.668 (2)H32···H212.51 (6)
C11···O1ii3.267 (3)H32···H222.21 (6)
C8···H12i3.0800H32···H22vi2.40 (6)
C8···H2A2.7500H32···O21.87 (5)
C7—S1—C8102.18 (9)O1—C9—C10109.90 (19)
C9—O1—C12106.11 (17)O1—C9—C8116.32 (16)
H21—O2—H22108 (4)C9—C10—C11106.86 (18)
H31—O3—H32106 (3)C10—C11—C12106.66 (19)
C1—N1—C7109.38 (16)O1—C12—C11110.4 (2)
C6—N2—C7109.01 (16)C1—C2—H2122.00
C7—N1—H1125.00C3—C2—H2122.00
C1—N1—H1125.00C4—C3—H3119.00
C7—N2—H2A125.00C2—C3—H3119.00
C6—N2—H2A126.00C5—C4—H4119.00
C2—C1—C6121.30 (18)C3—C4—H4119.00
N1—C1—C2132.42 (18)C6—C5—H5122.00
N1—C1—C6106.27 (16)C4—C5—H5122.00
C1—C2—C3116.37 (19)S1—C8—H8A109.00
C2—C3—C4121.8 (2)C9—C8—H8B109.00
C3—C4—C5122.05 (19)S1—C8—H8B109.00
C4—C5—C6116.35 (18)C9—C8—H8A109.00
C1—C6—C5122.17 (18)H8A—C8—H8B107.00
N2—C6—C5131.46 (18)C11—C10—H10127.00
N2—C6—C1106.38 (16)C9—C10—H10127.00
S1—C7—N1122.31 (15)C10—C11—H11127.00
S1—C7—N2128.73 (15)C12—C11—H11127.00
N1—C7—N2108.96 (17)C11—C12—H12125.00
S1—C8—C9114.64 (14)O1—C12—H12125.00
C8—C9—C10133.77 (19)
C8—S1—C7—N1164.63 (17)C2—C1—C6—N2−179.44 (19)
C8—S1—C7—N2−16.5 (2)C2—C1—C6—C50.5 (3)
C7—S1—C8—C9−74.29 (16)N1—C1—C2—C3−179.4 (2)
C12—O1—C9—C8−179.37 (18)N1—C1—C6—C5179.77 (19)
C9—O1—C12—C11−0.9 (3)C1—C2—C3—C40.2 (3)
C12—O1—C9—C101.4 (2)C2—C3—C4—C5−0.2 (3)
C1—N1—C7—N2−0.5 (2)C3—C4—C5—C60.4 (3)
C7—N1—C1—C60.4 (2)C4—C5—C6—C1−0.5 (3)
C7—N1—C1—C2179.6 (2)C4—C5—C6—N2179.4 (2)
C1—N1—C7—S1178.54 (15)S1—C8—C9—O1−77.85 (19)
C6—N2—C7—S1−178.54 (17)S1—C8—C9—C10101.1 (2)
C6—N2—C7—N10.4 (2)O1—C9—C10—C11−1.3 (2)
C7—N2—C6—C5179.9 (2)C8—C9—C10—C11179.6 (2)
C7—N2—C6—C1−0.2 (2)C9—C10—C11—C120.7 (3)
N1—C1—C6—N2−0.1 (2)C10—C11—C12—O10.1 (3)
C6—C1—C2—C3−0.3 (3)
Symmetry codes: (i) x+1, y, z; (ii) x, −y+1/2, z+1/2; (iii) x+1, −y+1/2, z+1/2; (iv) x, −y+1/2, z−1/2; (v) x−1, y, z; (vi) −x, −y, −z+2; (vii) x, y, z+1; (viii) −x, −y, −z+1; (ix) x, y, z−1; (x) −x+1, −y, −z+1; (xi) −x, y+1/2, −z+3/2; (xii) −x, y−1/2, −z+3/2; (xiii) x−1, −y+1/2, z−1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3ix0.861.882.738 (2)177
N2—H2A···Cl10.862.293.1032 (17)159
O2—H21···Cl1v0.93 (4)2.25 (4)3.178 (2)177 (4)
O2—H22···O3vi0.77 (4)2.11 (4)2.850 (3)162 (4)
O3—H31···Cl10.83 (3)2.33 (3)3.145 (2)170 (3)
O3—H32···O20.93 (4)1.87 (5)2.763 (3)160 (4)
C12—H12···Cl1xiii0.932.823.673 (3)152
Symmetry codes: (v) x−1, y, z; (vi) −x, −y, −z+2; (ix) x, y, z−1; (xiii) x−1, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formulaC12H11N2OS+·Cl−·2H2O
Mr302.78
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)7.0649 (6), 21.5994 (17), 9.5520 (7)
β (°) 97.925 (6)
V (Å3)1443.7 (2)
Z4
Radiation typeMo Kα
µ (mm−1)0.41
Crystal size (mm)0.51 × 0.42 × 0.32
Data collection
DiffractometerStoe IPDS2
Absorption correctionIntegration
(X-RED32; Stoe & Cie, 2002)
Tmin, Tmax0.817, 0.879
No. of measured, independent and
observed [I > 2σ(I)] reflections		12197, 3158, 1882
Rint0.045
(sin θ/λ)max (Å−1)0.642
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.093, 0.84
No. of reflections3158
No. of parameters189
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.19, −0.25

Computer programs: X-AREA (Stoe & Cie, 2002), X-AREA, X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top
S1—C71.717 (2)N1—C11.391 (2)
S1—C81.828 (2)N2—C61.392 (2)
N1—C71.329 (2)N2—C71.337 (2)
C7—S1—C8102.18 (9)S1—C7—N2128.73 (15)
C9—O1—C12106.11 (17)S1—C8—C9114.64 (14)
S1—C7—N1122.31 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.861.882.738 (2)177
N2—H2A···Cl10.862.293.1032 (17)159
O2—H21···Cl1ii0.93 (4)2.25 (4)3.178 (2)177 (4)
O2—H22···O3iii0.77 (4)2.11 (4)2.850 (3)162 (4)
O3—H31···Cl10.83 (3)2.33 (3)3.145 (2)170 (3)
O3—H32···O20.93 (4)1.87 (5)2.763 (3)160 (4)
C12—H12···Cl1iv0.932.823.673 (3)152
Symmetry codes: (i) x, y, z−1; (ii) x−1, y, z; (iii) −x, −y, −z+2; (iv) x−1, −y+1/2, z−1/2.
 

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