Buy article online - an online subscription or single-article purchase is required to access this article.
In the title compound, thiabendazolium perchlorate [2-(4-thiazolyl)-1
H-benzimidazol-1-ium perchlorate], C
10H
8N
3S
+·ClO
4−, one of the N atoms of the benzimidazole moiety is protonated rather than that in the thiazole group. This protonation leads to equalization of the bond angles at the two N atoms of the benzimidazole group. The C—C bond connecting the two ring systems has a length of 1.455 (7) Å. The dihedral angle between the benzimidazole system and the thiazole ring is 10.4 (3)°. The perchlorate anions bridge the thiabendazolium cations through a pair of N—H
O hydrogen bonds, leading to a hydrogen-bonded supramolecular chain.
Supporting information
CCDC reference: 183801
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.008 Å
- R factor = 0.068
- wR factor = 0.182
- Data-to-parameter ratio = 10.8
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 1990).
Crystal data top
C10H8N3S+·ClO4− | F(000) = 616 |
Mr = 301.71 | Dx = 1.646 Mg m−3 |
Monoclinic, P21/a | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yab | Cell parameters from 25 reflections |
a = 14.121 (15) Å | θ = 10–15° |
b = 5.245 (2) Å | µ = 0.50 mm−1 |
c = 17.384 (15) Å | T = 293 K |
β = 108.99 (11)° | Needle, colourless |
V = 1217.4 (19) Å3 | 0.30 × 0.30 × 0.15 mm |
Z = 4 | |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.018 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.5° |
Graphite monochromator | h = 0→16 |
ω–2θ scans | k = 0→6 |
2238 measured reflections | l = −20→19 |
2136 independent reflections | 2 standard reflections every 60 min |
1447 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.182 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.22 | w = 1/[σ2(Fo2) + (0.0544P)2 + 2.689P] where P = (Fo2 + 2Fc2)/3 |
2136 reflections | (Δ/σ)max < 0.001 |
198 parameters | Δρmax = 0.73 e Å−3 |
0 restraints | Δρmin = −0.63 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All e.s.d.'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 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.48723 (9) | 0.9113 (3) | 0.24362 (9) | 0.0557 (5) | |
O1 | 0.3863 (3) | 0.8527 (11) | 0.2121 (3) | 0.100 (2) | |
O2 | 0.5422 (3) | 0.8082 (10) | 0.1967 (3) | 0.0870 (19) | |
O3 | 0.5199 (7) | 0.822 (3) | 0.3180 (4) | 0.296 (10) | |
O4 | 0.4888 (7) | 1.1712 (14) | 0.2379 (9) | 0.259 (7) | |
S1 | 0.14255 (12) | 0.5237 (3) | −0.01476 (9) | 0.0605 (5) | |
N1 | 0.1919 (3) | 0.0856 (8) | 0.2474 (2) | 0.0419 (11) | |
N3 | 0.2995 (3) | 0.3906 (8) | 0.2638 (2) | 0.0451 (12) | |
N13 | 0.1171 (3) | 0.1600 (9) | 0.0744 (3) | 0.0510 (16) | |
C2 | 0.2237 (3) | 0.2715 (9) | 0.2099 (3) | 0.0410 (16) | |
C4 | 0.3916 (4) | 0.3241 (13) | 0.4141 (3) | 0.0584 (19) | |
C5 | 0.3898 (4) | 0.1683 (13) | 0.4770 (3) | 0.0610 (19) | |
C6 | 0.3207 (4) | −0.0278 (13) | 0.4675 (4) | 0.059 (2) | |
C7 | 0.2490 (4) | −0.0729 (11) | 0.3931 (3) | 0.0519 (17) | |
C8 | 0.2501 (3) | 0.0818 (9) | 0.3292 (3) | 0.0400 (16) | |
C9 | 0.3192 (3) | 0.2790 (10) | 0.3396 (3) | 0.0451 (17) | |
C10 | 0.1836 (3) | 0.3288 (10) | 0.1234 (3) | 0.0411 (16) | |
C11 | 0.2054 (4) | 0.5340 (11) | 0.0865 (3) | 0.0540 (19) | |
C12 | 0.0903 (4) | 0.2415 (12) | −0.0005 (3) | 0.0549 (19) | |
H1 | 0.14310 | −0.01620 | 0.22463 | 0.0505* | |
H3 | 0.33158 | 0.51799 | 0.25318 | 0.0539* | |
H4 | 0.439 (5) | 0.473 (13) | 0.422 (4) | 0.08 (2)* | |
H5 | 0.442 (4) | 0.199 (12) | 0.531 (3) | 0.071 (17)* | |
H6 | 0.327 (4) | −0.132 (10) | 0.509 (3) | 0.048 (15)* | |
H7 | 0.199 (4) | −0.214 (11) | 0.386 (3) | 0.061 (16)* | |
H11 | 0.244 (4) | 0.656 (10) | 0.111 (3) | 0.049 (15)* | |
H12 | 0.046 (5) | 0.136 (13) | −0.044 (4) | 0.09 (2)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0381 (7) | 0.0670 (10) | 0.0637 (9) | −0.0035 (6) | 0.0191 (6) | −0.0158 (7) |
O1 | 0.055 (3) | 0.112 (4) | 0.127 (4) | −0.011 (3) | 0.020 (3) | −0.009 (4) |
O2 | 0.093 (3) | 0.096 (4) | 0.093 (3) | 0.044 (3) | 0.059 (3) | 0.022 (3) |
O3 | 0.185 (7) | 0.63 (3) | 0.055 (4) | 0.211 (12) | 0.016 (4) | 0.018 (8) |
O4 | 0.199 (8) | 0.088 (5) | 0.60 (2) | −0.070 (5) | 0.280 (12) | −0.122 (9) |
S1 | 0.0732 (10) | 0.0589 (10) | 0.0543 (8) | 0.0002 (8) | 0.0275 (7) | 0.0071 (7) |
N1 | 0.0331 (19) | 0.047 (2) | 0.047 (2) | −0.0074 (19) | 0.0148 (17) | −0.005 (2) |
N3 | 0.043 (2) | 0.044 (2) | 0.052 (2) | −0.011 (2) | 0.0207 (19) | −0.004 (2) |
N13 | 0.045 (2) | 0.052 (3) | 0.055 (3) | −0.008 (2) | 0.015 (2) | 0.001 (2) |
C2 | 0.035 (2) | 0.041 (3) | 0.052 (3) | −0.001 (2) | 0.021 (2) | −0.005 (2) |
C4 | 0.053 (3) | 0.066 (4) | 0.055 (3) | −0.014 (3) | 0.016 (3) | −0.015 (3) |
C5 | 0.048 (3) | 0.081 (4) | 0.047 (3) | −0.005 (3) | 0.006 (3) | −0.012 (3) |
C6 | 0.062 (4) | 0.065 (4) | 0.048 (3) | 0.002 (3) | 0.016 (3) | 0.004 (3) |
C7 | 0.051 (3) | 0.051 (3) | 0.055 (3) | −0.009 (3) | 0.019 (3) | 0.000 (3) |
C8 | 0.034 (2) | 0.043 (3) | 0.044 (3) | −0.004 (2) | 0.014 (2) | −0.005 (2) |
C9 | 0.041 (3) | 0.048 (3) | 0.050 (3) | −0.003 (2) | 0.020 (2) | −0.007 (2) |
C10 | 0.036 (2) | 0.042 (3) | 0.051 (3) | 0.000 (2) | 0.022 (2) | −0.003 (2) |
C11 | 0.063 (4) | 0.046 (3) | 0.057 (3) | −0.012 (3) | 0.025 (3) | −0.008 (3) |
C12 | 0.050 (3) | 0.062 (4) | 0.051 (3) | −0.001 (3) | 0.014 (3) | 0.002 (3) |
Geometric parameters (Å, º) top
Cl1—O1 | 1.385 (5) | C2—C10 | 1.455 (7) |
Cl1—O2 | 1.404 (5) | C4—C9 | 1.384 (7) |
Cl1—O3 | 1.310 (9) | C4—C5 | 1.372 (8) |
Cl1—O4 | 1.368 (8) | C5—C6 | 1.390 (9) |
S1—C11 | 1.695 (5) | C6—C7 | 1.379 (8) |
S1—C12 | 1.708 (7) | C7—C8 | 1.380 (7) |
N1—C2 | 1.330 (6) | C8—C9 | 1.393 (7) |
N1—C8 | 1.392 (6) | C10—C11 | 1.339 (8) |
N3—C2 | 1.327 (6) | C4—H4 | 1.01 (7) |
N3—C9 | 1.385 (6) | C5—H5 | 1.00 (5) |
N13—C10 | 1.368 (7) | C6—H6 | 0.89 (5) |
N13—C12 | 1.304 (7) | C7—H7 | 1.00 (6) |
N1—H1 | 0.8597 | C11—H11 | 0.86 (6) |
N3—H3 | 0.8603 | C12—H12 | 0.98 (7) |
| | | |
Cl1···H3 | 3.0581 | C2···O2x | 3.331 (8) |
Cl1···H1i | 3.1178 | C5···O3vii | 3.372 (9) |
S1···C12ii | 3.601 (7) | C5···C5xii | 3.438 (9) |
S1···O1iii | 3.439 (6) | C7···O3ix | 3.336 (13) |
O1···N3 | 2.984 (8) | C10···O2x | 3.300 (8) |
O1···N1iv | 3.240 (7) | C11···O1 | 3.234 (8) |
O1···S1v | 3.439 (6) | C12···C12xi | 3.599 (9) |
O1···C2iv | 3.169 (8) | C12···S1ii | 3.601 (7) |
O1···C11 | 3.234 (8) | C12···O2iii | 3.332 (8) |
O2···C10vi | 3.300 (8) | C5···H7xiii | 3.09 (5) |
O2···C12v | 3.332 (8) | C5···H5xii | 3.10 (6) |
O2···N1i | 2.881 (7) | C6···H6xiii | 3.06 (6) |
O2···C2vi | 3.331 (8) | C11···H3 | 2.8667 |
O3···C7i | 3.336 (13) | C12···H12xi | 3.03 (7) |
O3···C5vii | 3.372 (9) | H1···N13 | 2.6805 |
O4···N1vi | 3.094 (12) | H1···Cl1ix | 3.1178 |
O4···N3iv | 3.075 (12) | H1···O2ix | 2.0399 |
O1···H3 | 2.1326 | H1···O4x | 2.8987 |
O1···H11 | 2.43 (5) | H3···Cl1 | 3.0581 |
O2···H1i | 2.0399 | H3···O1 | 2.1326 |
O2···H12v | 2.69 (7) | H3···C11 | 2.8667 |
O3···H7i | 2.48 (6) | H3···H11 | 2.4846 |
O3···H5vii | 2.50 (5) | H4···H5vii | 2.36 (9) |
O4···H1vi | 2.8987 | H5···O3vii | 2.50 (5) |
N1···O1viii | 3.240 (7) | H5···C5xii | 3.10 (6) |
N1···N13 | 2.871 (7) | H5···H4vii | 2.36 (9) |
N1···O2ix | 2.881 (7) | H6···C6xiv | 3.06 (6) |
N1···O4x | 3.094 (12) | H7···C5xiv | 3.09 (5) |
N3···O1 | 2.984 (8) | H7···O3ix | 2.48 (6) |
N3···O4viii | 3.075 (12) | H11···O1 | 2.43 (5) |
N13···N1 | 2.871 (7) | H11···N3 | 2.87 (5) |
N3···H11 | 2.87 (5) | H11···H3 | 2.4846 |
N13···H1 | 2.6805 | H12···O2iii | 2.69 (7) |
N13···H12xi | 2.68 (7) | H12···N13xi | 2.68 (7) |
C2···O1viii | 3.169 (8) | H12···C12xi | 3.03 (7) |
| | | |
O1—Cl1—O2 | 112.1 (3) | C7—C8—C9 | 121.5 (5) |
O1—Cl1—O3 | 107.3 (5) | N1—C8—C7 | 132.3 (5) |
O1—Cl1—O4 | 103.4 (6) | N3—C9—C4 | 132.6 (5) |
O2—Cl1—O3 | 110.6 (6) | N3—C9—C8 | 106.0 (4) |
O2—Cl1—O4 | 108.5 (6) | C4—C9—C8 | 121.4 (5) |
O3—Cl1—O4 | 114.8 (9) | N13—C10—C2 | 117.9 (5) |
C11—S1—C12 | 89.0 (3) | C2—C10—C11 | 126.0 (5) |
C2—N1—C8 | 109.3 (4) | N13—C10—C11 | 116.1 (5) |
C2—N3—C9 | 109.8 (4) | S1—C11—C10 | 110.3 (4) |
C10—N13—C12 | 109.1 (5) | S1—C12—N13 | 115.5 (4) |
C2—N1—H1 | 125.29 | C5—C4—H4 | 122 (4) |
C8—N1—H1 | 125.44 | C9—C4—H4 | 121 (4) |
C2—N3—H3 | 125.04 | C4—C5—H5 | 117 (3) |
C9—N3—H3 | 125.15 | C6—C5—H5 | 120 (3) |
N1—C2—C10 | 125.3 (4) | C5—C6—H6 | 119 (4) |
N3—C2—C10 | 125.8 (4) | C7—C6—H6 | 120 (4) |
N1—C2—N3 | 108.8 (4) | C6—C7—H7 | 121 (3) |
C5—C4—C9 | 116.4 (6) | C8—C7—H7 | 122 (3) |
C4—C5—C6 | 122.7 (5) | S1—C11—H11 | 125 (3) |
C5—C6—C7 | 120.7 (6) | C10—C11—H11 | 125 (3) |
C6—C7—C8 | 117.2 (5) | S1—C12—H12 | 125 (4) |
N1—C8—C9 | 106.1 (4) | N13—C12—H12 | 119 (4) |
| | | |
C12—S1—C11—C10 | 0.2 (5) | N3—C2—C10—N13 | 168.9 (5) |
C11—S1—C12—N13 | 0.3 (5) | N3—C2—C10—C11 | −11.3 (8) |
C8—N1—C2—C10 | 177.7 (5) | C5—C4—C9—N3 | −178.3 (6) |
C2—N1—C8—C7 | −179.0 (6) | C9—C4—C5—C6 | 1.0 (9) |
C8—N1—C2—N3 | −0.6 (6) | C5—C4—C9—C8 | −1.5 (8) |
C2—N1—C8—C9 | 0.5 (5) | C4—C5—C6—C7 | −0.7 (10) |
C9—N3—C2—C10 | −177.8 (5) | C5—C6—C7—C8 | 0.9 (9) |
C9—N3—C2—N1 | 0.4 (6) | C6—C7—C8—N1 | 178.1 (5) |
C2—N3—C9—C8 | −0.1 (6) | C6—C7—C8—C9 | −1.4 (8) |
C2—N3—C9—C4 | 177.1 (6) | C7—C8—C9—N3 | 179.4 (5) |
C12—N13—C10—C11 | 0.8 (7) | N1—C8—C9—N3 | −0.2 (5) |
C12—N13—C10—C2 | −179.4 (5) | C7—C8—C9—C4 | 1.8 (8) |
C10—N13—C12—S1 | −0.6 (6) | N1—C8—C9—C4 | −177.8 (5) |
N1—C2—C10—N13 | −9.0 (7) | N13—C10—C11—S1 | −0.6 (6) |
N1—C2—C10—C11 | 170.7 (5) | C2—C10—C11—S1 | 179.7 (4) |
Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) −x, −y+1, −z; (iii) −x+1/2, y−1/2, −z; (iv) x, y+1, z; (v) −x+1/2, y+1/2, −z; (vi) x+1/2, −y+3/2, z; (vii) −x+1, −y+1, −z+1; (viii) x, y−1, z; (ix) x−1/2, −y+1/2, z; (x) x−1/2, −y+3/2, z; (xi) −x, −y, −z; (xii) −x+1, −y, −z+1; (xiii) −x+1/2, y+1/2, −z+1; (xiv) −x+1/2, y−1/2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2ix | 0.8597 | 2.0399 | 2.881 (7) | 165.70 |
N3—H3···O1 | 0.8603 | 2.1326 | 2.984 (8) | 169.94 |
C5—H5···O3vii | 1.00 (5) | 2.50 (5) | 3.372 (9) | 145 (5) |
C7—H7···O3ix | 1.00 (6) | 2.48 (6) | 3.336 (13) | 143 (4) |
C11—H11···O1 | 0.86 (6) | 2.43 (5) | 3.234 (8) | 157 (4) |
Symmetry codes: (vii) −x+1, −y+1, −z+1; (ix) x−1/2, −y+1/2, z. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.