A hydrogen-bonded supramolecular chain in thiabendazolium perchlorate

In the title compound, thia­bendazolium perchlorate [2-(4-thia­zolyl)-1H-benzimidazol-1-ium perchlorate], C₁₀H₈N₃S⁺·ClO₄⁻, 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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

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Computing details

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).

(I)

Crystal data

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) Å^3	0.30 × 0.30 × 0.15 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.182	H atoms treated by a mixture of independent and constrained refinement
S = 1.22	w = 1/[σ^2(Fo^2) + (0.0544P)^2 + 2.689P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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···O2^x	3.331 (8)
Cl1···H1^i	3.1178	C5···O3^vii	3.372 (9)
S1···C12^ii	3.601 (7)	C5···C5^xii	3.438 (9)
S1···O1^iii	3.439 (6)	C7···O3^ix	3.336 (13)
O1···N3	2.984 (8)	C10···O2^x	3.300 (8)
O1···N1^iv	3.240 (7)	C11···O1	3.234 (8)
O1···S1^v	3.439 (6)	C12···C12^xi	3.599 (9)
O1···C2^iv	3.169 (8)	C12···S1^ii	3.601 (7)
O1···C11	3.234 (8)	C12···O2^iii	3.332 (8)
O2···C10^vi	3.300 (8)	C5···H7^xiii	3.09 (5)
O2···C12^v	3.332 (8)	C5···H5^xii	3.10 (6)
O2···N1^i	2.881 (7)	C6···H6^xiii	3.06 (6)
O2···C2^vi	3.331 (8)	C11···H3	2.8667
O3···C7^i	3.336 (13)	C12···H12^xi	3.03 (7)
O3···C5^vii	3.372 (9)	H1···N13	2.6805
O4···N1^vi	3.094 (12)	H1···Cl1^ix	3.1178
O4···N3^iv	3.075 (12)	H1···O2^ix	2.0399
O1···H3	2.1326	H1···O4^x	2.8987
O1···H11	2.43 (5)	H3···Cl1	3.0581
O2···H1^i	2.0399	H3···O1	2.1326
O2···H12^v	2.69 (7)	H3···C11	2.8667
O3···H7^i	2.48 (6)	H3···H11	2.4846
O3···H5^vii	2.50 (5)	H4···H5^vii	2.36 (9)
O4···H1^vi	2.8987	H5···O3^vii	2.50 (5)
N1···O1^viii	3.240 (7)	H5···C5^xii	3.10 (6)
N1···N13	2.871 (7)	H5···H4^vii	2.36 (9)
N1···O2^ix	2.881 (7)	H6···C6^xiv	3.06 (6)
N1···O4^x	3.094 (12)	H7···C5^xiv	3.09 (5)
N3···O1	2.984 (8)	H7···O3^ix	2.48 (6)
N3···O4^viii	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···O2^iii	2.69 (7)
N13···H12^xi	2.68 (7)	H12···N13^xi	2.68 (7)
C2···O1^viii	3.169 (8)	H12···C12^xi	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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^ix	0.8597	2.0399	2.881 (7)	165.70
N3—H3···O1	0.8603	2.1326	2.984 (8)	169.94
C5—H5···O3^vii	1.00 (5)	2.50 (5)	3.372 (9)	145 (5)
C7—H7···O3^ix	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.