2-(1,3-Thia-zol-4-yl)benzimidazolium nitrate monohydrate.

In the title compound, C(10)H(8)N(3)S(+)·NO(3) (-)·H(2)O, one of the N atoms of the benzimidazole unit is protonated, unlike than that in the thia-zole group. This protonation leads to equalization of the bond angles at the two N atoms of the benzimidazole group. The benzimidazole and thia-zole systems are almost coplanar, forming a dihedral angle of 0.5 (2)°. In the crystal, the nitrate anion and water mol-ecule bridge the thia-bendazolium cations through N-H⋯O and O-H⋯O hydrogen bonds, leading to a supra-molecular network based on an infinite one-dimensional chain using [001] as base vector.

Related literature

For the anti­viral action and anthelmintic activity of substituted benzimidazoles, see: Goodgame et al. (1985 ▶). Related structures have been reported: thia­bendazole (Trus & Marsh, 1973 ▶); thia­bendazolium n class="Chemical">nitrate (Murugesan et al., 1998 ▶; Devereux et al., 2004 ▶); thia­bendazolium perchlorate (Stanley et al., 2002 ▶); thia­bendazolium halide dihydrates (Prabakaran et al., 2000 ▶). For structures of transition metal complexes bearing thia­bendazole as ligand, see: Kowala & Wunderlich (1973 ▶); Udupa & Krebs (1979 ▶); Rong et al. (1991 ▶).

Experimental

Crystal data

C10H8N3S+·NO3 −·H2O

M = 282.28

Monoclinic,

a = 7.6140 (3) Å

b = 16.3130 (5) Å

c = 10.0990 (3) Å

β = 102.731 (4)°

V = 1223.53 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 298 K

0.54 × 0.39 × 0.26 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini Mo) detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.920, T max = 0.952

5590 measured reflections

2426 independent reflections

1859 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.100

S = 1.08

2426 reflections

184 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis n class="Disease">RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810008433/bh2274sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008433/bh2274Isup2.hkl

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

C10H8N3S+·NO3−·H2O	F(000) = 584
Mr = 282.28	Dx = 1.532 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3277 reflections
a = 7.6140 (3) Å	θ = 3.2–26.0°
b = 16.3130 (5) Å	µ = 0.28 mm−1
c = 10.0990 (3) Å	T = 298 K
β = 102.731 (4)°	Prism, pale yellow
V = 1223.53 (7) Å3	0.54 × 0.39 × 0.26 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini Mo) detector	2426 independent reflections
Radiation source: X-ray	1859 reflections with I > 2σ(I)
graphite	Rint = 0.017
Detector resolution: 10.4685 pixels mm-1	θmax = 26.1°, θmin = 3.2°
ω scans	h = −9→7
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −19→20
Tmin = 0.920, Tmax = 0.952	l = −12→10
5590 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0565P)2 + 0.057P] where P = (Fo2 + 2Fc2)/3
2426 reflections	(Δ/σ)max < 0.001
184 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.21 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
C2	0.7417 (2)	−0.01688 (10)	0.01259 (16)	0.0385 (4)
C4	0.8456 (2)	0.11013 (10)	0.02130 (18)	0.0416 (4)
C5	0.8891 (3)	0.18937 (11)	−0.0082 (2)	0.0542 (5)
H5	0.8578	0.2102	−0.096	0.065*
C6	0.9813 (3)	0.23603 (12)	0.0988 (2)	0.0606 (5)
H6	1.0132	0.2897	0.084	0.073*
C7	1.0266 (2)	0.20260 (12)	0.2293 (2)	0.0576 (5)
H7	1.0923	0.2346	0.2992	0.069*
C8	0.9784 (2)	0.12463 (12)	0.25917 (19)	0.0517 (5)
H8	1.0062	0.1042	0.3473	0.062*
C9	0.8865 (2)	0.07819 (10)	0.15118 (16)	0.0416 (4)
C10	0.6544 (2)	−0.09278 (9)	−0.03838 (16)	0.0387 (4)
C11	0.5761 (2)	−0.10865 (11)	−0.17031 (17)	0.0467 (4)
H11	0.5695	−0.0718	−0.2415	0.056*
C13	0.5667 (3)	−0.21780 (11)	−0.01579 (18)	0.0507 (4)
H13	0.5495	−0.2667	0.027	0.061*
N1	0.81909 (19)	−0.00164 (8)	0.14122 (14)	0.0403 (3)
N3	0.7559 (2)	0.04857 (9)	−0.06229 (15)	0.0434 (4)
N14	0.6484 (2)	−0.15582 (9)	0.05111 (15)	0.0487 (4)
N15	0.6705 (2)	0.07673 (9)	0.58671 (15)	0.0502 (4)
O1W	0.2195 (2)	0.07887 (10)	0.62504 (15)	0.0621 (4)
O16	0.7817 (3)	0.02340 (12)	0.61835 (19)	0.1061 (7)
O17	0.6049 (2)	0.10779 (9)	0.67836 (14)	0.0724 (4)
O18	0.6223 (3)	0.09795 (10)	0.47009 (14)	0.0989 (6)
S12	0.49270 (6)	−0.20485 (3)	−0.18646 (4)	0.05076 (18)
H2D	0.329 (3)	0.0937 (14)	0.647 (2)	0.076*
H1D	0.205 (3)	0.0427 (15)	0.574 (2)	0.076*
H1N	0.814 (3)	−0.0313 (12)	0.210 (2)	0.061*
H3N	0.722 (3)	0.0536 (13)	−0.145 (2)	0.061*

	U11	U22	U33	U12	U13	U23
C2	0.0382 (9)	0.0415 (9)	0.0363 (9)	0.0061 (7)	0.0094 (7)	0.0024 (7)
C4	0.0385 (9)	0.0433 (9)	0.0447 (9)	−0.0003 (7)	0.0131 (7)	0.0001 (7)
C5	0.0536 (11)	0.0513 (11)	0.0609 (12)	−0.0058 (8)	0.0193 (10)	0.0072 (9)
C6	0.0486 (11)	0.0507 (11)	0.0877 (16)	−0.0080 (9)	0.0261 (11)	−0.0116 (11)
C7	0.0421 (10)	0.0577 (12)	0.0726 (13)	−0.0018 (8)	0.0119 (9)	−0.0247 (10)
C8	0.0462 (10)	0.0564 (11)	0.0496 (10)	0.0067 (8)	0.0041 (8)	−0.0116 (9)
C9	0.0379 (9)	0.0435 (9)	0.0437 (9)	0.0060 (7)	0.0100 (7)	−0.0020 (8)
C10	0.0369 (9)	0.0413 (9)	0.0385 (9)	0.0043 (7)	0.0098 (7)	0.0007 (7)
C11	0.0543 (11)	0.0477 (10)	0.0371 (9)	0.0004 (8)	0.0080 (8)	0.0035 (7)
C13	0.0614 (11)	0.0457 (10)	0.0452 (10)	−0.0069 (8)	0.0124 (9)	0.0037 (8)
N1	0.0464 (8)	0.0403 (8)	0.0337 (7)	0.0064 (6)	0.0076 (6)	0.0026 (6)
N3	0.0473 (9)	0.0488 (8)	0.0340 (7)	−0.0021 (6)	0.0086 (7)	0.0057 (7)
N14	0.0591 (9)	0.0464 (8)	0.0390 (8)	−0.0046 (7)	0.0070 (7)	0.0044 (7)
N15	0.0613 (10)	0.0447 (8)	0.0414 (8)	0.0024 (7)	0.0044 (7)	0.0033 (7)
O1W	0.0733 (10)	0.0623 (9)	0.0512 (8)	0.0057 (8)	0.0149 (8)	0.0038 (6)
O16	0.1230 (16)	0.1025 (14)	0.0874 (12)	0.0633 (12)	0.0118 (11)	0.0130 (10)
O17	0.0828 (11)	0.0859 (11)	0.0469 (8)	0.0184 (8)	0.0104 (7)	−0.0106 (7)
O18	0.1616 (18)	0.0918 (12)	0.0357 (8)	0.0366 (11)	0.0057 (10)	0.0079 (7)
S12	0.0541 (3)	0.0533 (3)	0.0437 (3)	−0.0063 (2)	0.0082 (2)	−0.0065 (2)

N1—C2	1.326 (2)	C8—C9	1.385 (2)
N1—C9	1.395 (2)	C8—H8	0.93
N3—C2	1.327 (2)	C10—C11	1.359 (2)
N3—C4	1.390 (2)	C11—S12	1.6874 (18)
N14—C10	1.376 (2)	C11—H11	0.93
N14—C13	1.296 (2)	C13—S12	1.7045 (19)
C2—C10	1.445 (2)	C13—H13	0.93
C4—C9	1.382 (2)	N1—H1N	0.85 (2)
C4—C5	1.383 (2)	N3—H3N	0.82 (2)
C5—C6	1.380 (3)	N15—O18	1.205 (2)
C5—H5	0.93	N15—O16	1.207 (2)
C6—C7	1.398 (3)	N15—O17	1.2516 (19)
C6—H6	0.93	O1W—H2D	0.85 (2)
C7—C8	1.375 (3)	O1W—H1D	0.78 (2)
C7—H7	0.93
C2—N1—C9	108.82 (13)	C7—C8—H8	121.7
C2—N1—H1N	126.9 (14)	C9—C8—H8	121.7
C9—N1—H1N	123.4 (13)	C4—C9—C8	120.69 (16)
C2—N3—C4	109.03 (14)	C4—C9—N1	106.34 (14)
C2—N3—H3N	127.8 (15)	C8—C9—N1	132.97 (16)
C4—N3—H3N	123.2 (15)	C11—C10—N14	115.50 (15)
N1—C2—N3	109.45 (15)	C11—C10—C2	125.47 (15)
N1—C2—C10	125.43 (14)	N14—C10—C2	119.03 (14)
N3—C2—C10	125.13 (15)	C10—C11—S12	110.26 (13)
C9—C4—C5	122.87 (17)	C10—C11—H11	124.9
C9—C4—N3	106.36 (14)	S12—C11—H11	124.9
C5—C4—N3	130.76 (16)	N14—C13—S12	116.36 (14)
C6—C5—C4	116.81 (19)	N14—C13—H13	121.8
C6—C5—H5	121.6	S12—C13—H13	121.8
C4—C5—H5	121.6	C13—N14—C10	108.79 (15)
C5—C6—C7	120.04 (18)	O18—N15—O16	120.71 (18)
C5—C6—H6	120	O18—N15—O17	121.43 (17)
C7—C6—H6	120	O16—N15—O17	117.84 (16)
C8—C7—C6	123.02 (19)	O18—N15—O17	121.43 (17)
C8—C7—H7	118.5	O16—N15—O17	117.84 (16)
C6—C7—H7	118.5	H2D—O1W—H1D	112 (2)
C7—C8—C9	116.52 (18)	C11—S12—C13	89.08 (8)
C9—C4—C5—C6	1.6 (3)	N14—C10—C11—S12	−0.39 (19)
N3—C4—C5—C6	−179.56 (17)	C2—C10—C11—S12	179.16 (13)
C4—C5—C6—C7	0.2 (3)	N3—C2—N1—C9	0.41 (18)
C5—C6—C7—C8	−2.2 (3)	C10—C2—N1—C9	−179.28 (14)
C6—C7—C8—C9	2.3 (3)	C4—C9—N1—C2	−0.09 (17)
C5—C4—C9—C8	−1.5 (3)	C8—C9—N1—C2	−179.72 (17)
N3—C4—C9—C8	179.44 (14)	N1—C2—N3—C4	−0.58 (18)
C5—C4—C9—N1	178.82 (15)	C10—C2—N3—C4	179.11 (14)
N3—C4—C9—N1	−0.25 (17)	C9—C4—N3—C2	0.51 (18)
C7—C8—C9—C4	−0.5 (2)	C5—C4—N3—C2	−178.47 (18)
C7—C8—C9—N1	179.10 (16)	S12—C13—N14—C10	−0.2 (2)
N1—C2—C10—C11	−179.51 (16)	C11—C10—N14—C13	0.4 (2)
N3—C2—C10—C11	0.8 (3)	C2—C10—N14—C13	−179.21 (15)
N1—C2—C10—N14	0.0 (2)	C10—C11—S12—C13	0.22 (14)
N3—C2—C10—N14	−179.62 (15)	N14—C13—S12—C11	−0.01 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2D···O17	0.85 (2)	2.06 (2)	2.903 (2)	168 (2)
O1W—H1D···O16i	0.78 (2)	2.24 (3)	2.969 (2)	156 (2)
N1—H1N···O1Wi	0.85 (2)	1.91 (2)	2.748 (2)	168.5 (18)
N3—H3N···O16ii	0.82 (2)	2.58 (2)	3.300 (2)	147.5 (18)
N3—H3N···O17ii	0.82 (2)	2.02 (2)	2.791 (2)	157 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2D⋯O17	0.85 (2)	2.06 (2)	2.903 (2)	168 (2)
O1W—H1D⋯O16i	0.78 (2)	2.24 (3)	2.969 (2)	156 (2)
N1—H1N⋯O1Wi	0.85 (2)	1.91 (2)	2.748 (2)	168.5 (18)
N3—H3N⋯O16ii	0.82 (2)	2.58 (2)	3.300 (2)	147.5 (18)
N3—H3N⋯O17ii	0.82 (2)	2.02 (2)	2.791 (2)	157 (2)

Symmetry codes: (i) ; (ii) .