Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680701673X/bt2335sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680701673X/bt2335Isup2.hkl |
CCDC reference: 647569
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.036
- wR factor = 0.093
- Data-to-parameter ratio = 16.7
checkCIF/PLATON results
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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
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).
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%.
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).
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).
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).
C12H11N2OS+·Cl−·2H2O | F(000) = 632 |
Mr = 302.78 | Dx = 1.393 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 12416 reflections |
a = 7.0649 (6) Å | θ = 1.9–27.1° |
b = 21.5994 (17) Å | µ = 0.41 mm−1 |
c = 9.5520 (7) Å | T = 296 K |
β = 97.925 (6)° | Prism, colourless |
V = 1443.7 (2) Å3 | 0.51 × 0.42 × 0.32 mm |
Z = 4 |
Stoe IPDS2 diffractometer | 3158 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1882 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.045 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.1°, θmin = 1.9° |
ω scans | h = −9→9 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −27→27 |
Tmin = 0.817, Tmax = 0.879 | l = −12→12 |
12197 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)] = 0.036 | H 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 reflections | Δρmax = 0.19 e Å−3 |
189 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0078 (13) |
C12H11N2OS+·Cl−·2H2O | V = 1443.7 (2) Å3 |
Mr = 302.78 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.0649 (6) Å | µ = 0.41 mm−1 |
b = 21.5994 (17) Å | T = 296 K |
c = 9.5520 (7) Å | 0.51 × 0.42 × 0.32 mm |
β = 97.925 (6)° |
Stoe IPDS2 diffractometer | 3158 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 1882 reflections with I > 2σ(I) |
Tmin = 0.817, Tmax = 0.879 | Rint = 0.045 |
12197 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.093 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.84 | Δρmax = 0.19 e Å−3 |
3158 reflections | Δρmin = −0.25 e Å−3 |
189 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.28109 (10) | 0.18243 (3) | 0.44205 (7) | 0.0676 (2) | |
O1 | −0.0559 (2) | 0.26590 (7) | 0.57648 (17) | 0.0666 (6) | |
N1 | 0.2396 (2) | 0.05992 (7) | 0.41089 (17) | 0.0508 (6) | |
N2 | 0.3027 (2) | 0.08569 (7) | 0.63196 (17) | 0.0499 (5) | |
C1 | 0.2474 (3) | 0.00497 (9) | 0.4873 (2) | 0.0463 (6) | |
C2 | 0.2215 (3) | −0.05649 (10) | 0.4465 (2) | 0.0563 (8) | |
C3 | 0.2386 (3) | −0.09954 (10) | 0.5533 (3) | 0.0616 (8) | |
C4 | 0.2792 (3) | −0.08243 (10) | 0.6947 (2) | 0.0649 (9) | |
C5 | 0.3050 (3) | −0.02185 (10) | 0.7354 (2) | 0.0578 (8) | |
C6 | 0.2875 (3) | 0.02143 (9) | 0.6287 (2) | 0.0455 (6) | |
C7 | 0.2740 (3) | 0.10729 (9) | 0.4996 (2) | 0.0494 (7) | |
C8 | 0.2646 (3) | 0.22625 (9) | 0.6037 (2) | 0.0573 (8) | |
C9 | 0.0741 (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) | |
O3 | 0.1745 (3) | 0.06500 (8) | 1.12185 (18) | 0.0678 (6) | |
Cl1 | 0.44294 (7) | 0.13331 (2) | 0.93504 (6) | 0.0562 (2) | |
H1 | 0.21620 | 0.06280 | 0.32040 | 0.0610* | |
H2 | 0.19410 | −0.06790 | 0.35200 | 0.0680* | |
H2A | 0.32680 | 0.10790 | 0.70700 | 0.0600* | |
H3 | 0.22270 | −0.14130 | 0.53050 | 0.0740* | |
H4 | 0.28910 | −0.11310 | 0.76370 | 0.0780* | |
H5 | 0.33270 | −0.01060 | 0.83000 | 0.0690* | |
H8A | 0.35430 | 0.20890 | 0.67950 | 0.0690* | |
H8B | 0.30330 | 0.26860 | 0.58960 | 0.0690* | |
H10 | 0.05280 | 0.16620 | 0.80700 | 0.0650* | |
H11 | −0.28650 | 0.20500 | 0.79400 | 0.0760* | |
H12 | −0.33250 | 0.28100 | 0.60870 | 0.0820* | |
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)* | |
H31 | 0.252 (4) | 0.0849 (12) | 1.082 (3) | 0.084 (9)* | |
H32 | 0.055 (6) | 0.073 (2) | 1.070 (5) | 0.176 (18)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0905 (5) | 0.0574 (3) | 0.0611 (4) | 0.0132 (3) | 0.0330 (3) | 0.0147 (3) |
O1 | 0.0700 (10) | 0.0607 (9) | 0.0695 (11) | 0.0096 (8) | 0.0112 (8) | 0.0167 (8) |
N1 | 0.0570 (10) | 0.0601 (10) | 0.0360 (9) | 0.0062 (8) | 0.0094 (7) | 0.0019 (8) |
N2 | 0.0623 (10) | 0.0496 (9) | 0.0387 (9) | 0.0012 (8) | 0.0104 (8) | −0.0020 (7) |
C1 | 0.0454 (10) | 0.0544 (11) | 0.0401 (11) | 0.0048 (9) | 0.0090 (8) | 0.0007 (9) |
C2 | 0.0559 (13) | 0.0628 (13) | 0.0508 (13) | −0.0004 (10) | 0.0091 (10) | −0.0120 (10) |
C3 | 0.0666 (14) | 0.0517 (12) | 0.0667 (16) | −0.0010 (10) | 0.0103 (11) | −0.0067 (11) |
C4 | 0.0845 (17) | 0.0529 (12) | 0.0575 (15) | 0.0010 (11) | 0.0107 (12) | 0.0077 (11) |
C5 | 0.0730 (15) | 0.0573 (12) | 0.0430 (12) | 0.0007 (10) | 0.0081 (10) | 0.0039 (9) |
C6 | 0.0488 (11) | 0.0464 (10) | 0.0421 (11) | 0.0023 (8) | 0.0092 (8) | −0.0008 (8) |
C7 | 0.0515 (12) | 0.0556 (11) | 0.0430 (12) | 0.0068 (9) | 0.0137 (9) | 0.0049 (9) |
C8 | 0.0591 (13) | 0.0468 (11) | 0.0677 (15) | −0.0030 (9) | 0.0152 (11) | 0.0052 (10) |
C9 | 0.0534 (11) | 0.0415 (10) | 0.0487 (12) | 0.0012 (9) | 0.0053 (9) | −0.0025 (9) |
C10 | 0.0541 (12) | 0.0555 (12) | 0.0535 (13) | 0.0005 (9) | 0.0057 (10) | 0.0112 (10) |
C11 | 0.0580 (13) | 0.0800 (16) | 0.0527 (13) | −0.0050 (12) | 0.0136 (10) | 0.0011 (12) |
C12 | 0.0545 (14) | 0.0699 (14) | 0.0804 (18) | 0.0128 (11) | 0.0107 (12) | −0.0016 (13) |
O2 | 0.0754 (13) | 0.0817 (14) | 0.0744 (13) | 0.0137 (11) | 0.0066 (9) | 0.0059 (10) |
O3 | 0.0687 (11) | 0.0866 (12) | 0.0487 (10) | −0.0051 (9) | 0.0100 (8) | 0.0097 (8) |
Cl1 | 0.0560 (3) | 0.0628 (3) | 0.0493 (3) | −0.0030 (2) | 0.0055 (2) | −0.0033 (2) |
S1—C7 | 1.717 (2) | C3—C4 | 1.392 (3) |
S1—C8 | 1.828 (2) | C4—C5 | 1.370 (3) |
O1—C9 | 1.360 (2) | C5—C6 | 1.376 (3) |
O1—C12 | 1.367 (3) | C8—C9 | 1.466 (3) |
O2—H21 | 0.93 (4) | C9—C10 | 1.330 (3) |
O2—H22 | 0.77 (4) | C10—C11 | 1.416 (3) |
O3—H31 | 0.83 (3) | C11—C12 | 1.318 (3) |
O3—H32 | 0.93 (4) | C2—H2 | 0.9300 |
N1—C7 | 1.329 (2) | C3—H3 | 0.9300 |
N1—C1 | 1.391 (2) | C4—H4 | 0.9300 |
N2—C6 | 1.392 (2) | C5—H5 | 0.9300 |
N2—C7 | 1.337 (2) | C8—H8A | 0.9700 |
N1—H1 | 0.8600 | C8—H8B | 0.9700 |
N2—H2A | 0.8600 | C10—H10 | 0.9300 |
C1—C6 | 1.388 (3) | C11—H11 | 0.9300 |
C1—C2 | 1.389 (3) | C12—H12 | 0.9300 |
C2—C3 | 1.373 (3) | ||
Cl1···N2 | 3.1032 (17) | C10···H3viii | 3.1000 |
Cl1···O2i | 3.178 (2) | C10···H2A | 3.0800 |
Cl1···O3 | 3.145 (2) | C11···H3viii | 3.0300 |
Cl1···H11i | 2.9300 | C12···H3viii | 3.0000 |
Cl1···H2A | 2.2900 | C12···H4xi | 2.9800 |
Cl1···H8A | 2.9300 | H1···O3ix | 1.8800 |
Cl1···H10 | 2.9400 | H1···H31ix | 2.3700 |
Cl1···H8Bii | 2.8400 | H1···H32ix | 2.5100 |
Cl1···H21i | 2.25 (4) | H2···O2viii | 2.7000 |
Cl1···H31 | 2.33 (3) | H2A···Cl1 | 2.2900 |
Cl1···H12iii | 2.8200 | H2A···H8A | 2.2100 |
S1···O1 | 3.3780 (17) | H2A···H10 | 2.6000 |
S1···C9iv | 3.568 (2) | H2A···C8 | 2.7500 |
S1···C10iv | 3.668 (2) | H2A···C10 | 3.0800 |
O1···C10iv | 3.332 (3) | H3···C10viii | 3.1000 |
O1···S1 | 3.3780 (17) | H3···C12viii | 3.0000 |
O1···C11iv | 3.267 (3) | H3···C11viii | 3.0300 |
O2···Cl1v | 3.178 (2) | H4···H12xii | 2.5900 |
O2···O3vi | 2.850 (3) | H4···C12xii | 2.9800 |
O2···O3 | 2.763 (3) | H8A···N2 | 2.7200 |
O3···O2vi | 2.850 (3) | H8A···Cl1 | 2.9300 |
O3···Cl1 | 3.145 (2) | H8A···H2A | 2.2100 |
O3···N1vii | 2.738 (2) | H8B···H12i | 2.5700 |
O3···O2 | 2.763 (3) | H8B···Cl1iv | 2.8400 |
O2···H32 | 1.87 (5) | H10···Cl1 | 2.9400 |
O2···H2viii | 2.7000 | H10···H2A | 2.6000 |
O3···H22vi | 2.11 (4) | H11···Cl1v | 2.9300 |
O3···H1vii | 1.8800 | H12···C8v | 3.0800 |
N1···O3ix | 2.738 (2) | H12···Cl1xiii | 2.8200 |
N1···N2 | 2.170 (2) | H12···H8Bv | 2.5700 |
N2···N1 | 2.170 (2) | H12···H4xi | 2.5900 |
N2···Cl1 | 3.1032 (17) | H21···H32 | 2.51 (6) |
N2···H8A | 2.7200 | H21···Cl1v | 2.25 (4) |
C1···C1x | 3.550 (3) | H22···O3vi | 2.11 (4) |
C1···C1viii | 3.544 (3) | H22···H32vi | 2.40 (6) |
C3···C7x | 3.553 (3) | H22···H31vi | 2.53 (5) |
C3···C7viii | 3.591 (3) | H22···H32 | 2.21 (6) |
C7···C3viii | 3.591 (3) | H31···H22vi | 2.53 (5) |
C7···C3x | 3.553 (3) | H31···Cl1 | 2.33 (3) |
C9···S1ii | 3.568 (2) | H31···H1vii | 2.3700 |
C10···O1ii | 3.332 (3) | H32···H1vii | 2.5100 |
C10···S1ii | 3.668 (2) | H32···H21 | 2.51 (6) |
C11···O1ii | 3.267 (3) | H32···H22 | 2.21 (6) |
C8···H12i | 3.0800 | H32···H22vi | 2.40 (6) |
C8···H2A | 2.7500 | H32···O2 | 1.87 (5) |
C7—S1—C8 | 102.18 (9) | O1—C9—C10 | 109.90 (19) |
C9—O1—C12 | 106.11 (17) | O1—C9—C8 | 116.32 (16) |
H21—O2—H22 | 108 (4) | C9—C10—C11 | 106.86 (18) |
H31—O3—H32 | 106 (3) | C10—C11—C12 | 106.66 (19) |
C1—N1—C7 | 109.38 (16) | O1—C12—C11 | 110.4 (2) |
C6—N2—C7 | 109.01 (16) | C1—C2—H2 | 122.00 |
C7—N1—H1 | 125.00 | C3—C2—H2 | 122.00 |
C1—N1—H1 | 125.00 | C4—C3—H3 | 119.00 |
C7—N2—H2A | 125.00 | C2—C3—H3 | 119.00 |
C6—N2—H2A | 126.00 | C5—C4—H4 | 119.00 |
C2—C1—C6 | 121.30 (18) | C3—C4—H4 | 119.00 |
N1—C1—C2 | 132.42 (18) | C6—C5—H5 | 122.00 |
N1—C1—C6 | 106.27 (16) | C4—C5—H5 | 122.00 |
C1—C2—C3 | 116.37 (19) | S1—C8—H8A | 109.00 |
C2—C3—C4 | 121.8 (2) | C9—C8—H8B | 109.00 |
C3—C4—C5 | 122.05 (19) | S1—C8—H8B | 109.00 |
C4—C5—C6 | 116.35 (18) | C9—C8—H8A | 109.00 |
C1—C6—C5 | 122.17 (18) | H8A—C8—H8B | 107.00 |
N2—C6—C5 | 131.46 (18) | C11—C10—H10 | 127.00 |
N2—C6—C1 | 106.38 (16) | C9—C10—H10 | 127.00 |
S1—C7—N1 | 122.31 (15) | C10—C11—H11 | 127.00 |
S1—C7—N2 | 128.73 (15) | C12—C11—H11 | 127.00 |
N1—C7—N2 | 108.96 (17) | C11—C12—H12 | 125.00 |
S1—C8—C9 | 114.64 (14) | O1—C12—H12 | 125.00 |
C8—C9—C10 | 133.77 (19) | ||
C8—S1—C7—N1 | 164.63 (17) | C2—C1—C6—N2 | −179.44 (19) |
C8—S1—C7—N2 | −16.5 (2) | C2—C1—C6—C5 | 0.5 (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—C5 | 179.77 (19) |
C9—O1—C12—C11 | −0.9 (3) | C1—C2—C3—C4 | 0.2 (3) |
C12—O1—C9—C10 | 1.4 (2) | C2—C3—C4—C5 | −0.2 (3) |
C1—N1—C7—N2 | −0.5 (2) | C3—C4—C5—C6 | 0.4 (3) |
C7—N1—C1—C6 | 0.4 (2) | C4—C5—C6—C1 | −0.5 (3) |
C7—N1—C1—C2 | 179.6 (2) | C4—C5—C6—N2 | 179.4 (2) |
C1—N1—C7—S1 | 178.54 (15) | S1—C8—C9—O1 | −77.85 (19) |
C6—N2—C7—S1 | −178.54 (17) | S1—C8—C9—C10 | 101.1 (2) |
C6—N2—C7—N1 | 0.4 (2) | O1—C9—C10—C11 | −1.3 (2) |
C7—N2—C6—C5 | 179.9 (2) | C8—C9—C10—C11 | 179.6 (2) |
C7—N2—C6—C1 | −0.2 (2) | C9—C10—C11—C12 | 0.7 (3) |
N1—C1—C6—N2 | −0.1 (2) | C10—C11—C12—O1 | 0.1 (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. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3ix | 0.86 | 1.88 | 2.738 (2) | 177 |
N2—H2A···Cl1 | 0.86 | 2.29 | 3.1032 (17) | 159 |
O2—H21···Cl1v | 0.93 (4) | 2.25 (4) | 3.178 (2) | 177 (4) |
O2—H22···O3vi | 0.77 (4) | 2.11 (4) | 2.850 (3) | 162 (4) |
O3—H31···Cl1 | 0.83 (3) | 2.33 (3) | 3.145 (2) | 170 (3) |
O3—H32···O2 | 0.93 (4) | 1.87 (5) | 2.763 (3) | 160 (4) |
C12—H12···Cl1xiii | 0.93 | 2.82 | 3.673 (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 formula | C12H11N2OS+·Cl−·2H2O |
Mr | 302.78 |
Crystal system, space group | Monoclinic, 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) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.41 |
Crystal size (mm) | 0.51 × 0.42 × 0.32 |
Data collection | |
Diffractometer | Stoe IPDS2 |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.817, 0.879 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12197, 3158, 1882 |
Rint | 0.045 |
(sin θ/λ)max (Å−1) | 0.642 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.093, 0.84 |
No. of reflections | 3158 |
No. of parameters | 189 |
H-atom treatment | H 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).
S1—C7 | 1.717 (2) | N1—C1 | 1.391 (2) |
S1—C8 | 1.828 (2) | N2—C6 | 1.392 (2) |
N1—C7 | 1.329 (2) | N2—C7 | 1.337 (2) |
C7—S1—C8 | 102.18 (9) | S1—C7—N2 | 128.73 (15) |
C9—O1—C12 | 106.11 (17) | S1—C8—C9 | 114.64 (14) |
S1—C7—N1 | 122.31 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.86 | 1.88 | 2.738 (2) | 177 |
N2—H2A···Cl1 | 0.86 | 2.29 | 3.1032 (17) | 159 |
O2—H21···Cl1ii | 0.93 (4) | 2.25 (4) | 3.178 (2) | 177 (4) |
O2—H22···O3iii | 0.77 (4) | 2.11 (4) | 2.850 (3) | 162 (4) |
O3—H31···Cl1 | 0.83 (3) | 2.33 (3) | 3.145 (2) | 170 (3) |
O3—H32···O2 | 0.93 (4) | 1.87 (5) | 2.763 (3) | 160 (4) |
C12—H12···Cl1iv | 0.93 | 2.82 | 3.673 (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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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).