2-Thio-ureido-1H-benzimidazol-3-ium chloride monohydrate.

In the title compound, C8H9N4S(+)·Cl(-)·H2O, the cation is approximately planar, with a dihedral angle of 7.71 (8)° between the mean planes of the benzo-imidazole ring system and the thio-urea unit. In the crystal, cations, anions and water molecules of crystallization are linked by O-H⋯Cl, N-H⋯O, N-H⋯Cl and N-H⋯S hydrogen bonds into a three-dimensional network. π-π stacking is observed between the benzene and imidazole rings of neighbouring mol-ecules, the centroid-centroid distance being 3.5774 (11) Å.

Related literature

For the synthesis and biological activity of benzimidazoles, see: Siva & Subhash (2011 ▶); Sharghi et al. (2008 ▶); Refaat (2010 ▶); Puratchikody et al. (2008 ▶); Achar et al. (2010 ▶); Starcevic et al. (2007 ▶). For hydrogen-bond classification, see: Jeffrey et al. (1985 ▶).

Experimental

Crystal data

C8H9N4S+·Cl+·H2O

M = 246.72

Monoclinic,

a = 9.3027 (6) Å

b = 8.7038 (5) Å

c = 14.5503 (8) Å

β = 109.143 (3)°

V = 1112.97 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.51 mm−1

T = 293 K

0.33 × 0.19 × 0.14 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.850, T max = 0.932

10318 measured reflections

1958 independent reflections

1818 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.083

S = 1.07

1958 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814006837/xu5781sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814006837/xu5781Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814006837/xu5781Isup3.cml

CCDC reference: 994075

Additional supporting information: crystallographic information; 3D view; checkCIF report

C8H9N4S+·Cl+·H2O	F(000) = 512
Mr = 246.72	Dx = 1.472 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ybc	Cell parameters from 5220 reflections
a = 9.3027 (6) Å	θ = 2.3–27.9°
b = 8.7038 (5) Å	µ = 0.51 mm−1
c = 14.5503 (8) Å	T = 293 K
β = 109.143 (3)°	Block, yellow
V = 1112.97 (11) Å3	0.33 × 0.19 × 0.14 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	1958 independent reflections
Radiation source: fine-focus sealed tube	1818 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
Tmin = 0.850, Tmax = 0.932	k = −10→10
10318 measured reflections	l = −17→17

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.041P)2 + 0.391P] where P = (Fo2 + 2Fc2)/3
1958 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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	0.37873 (6)	−0.13735 (5)	0.83964 (4)	0.05278 (17)
N1	0.45104 (18)	0.12730 (17)	0.77931 (11)	0.0483 (4)
H1N	0.4545	0.2261	0.7785	0.058*
H2N	0.4887	0.0771	0.7417	0.058*
N2	0.33167 (17)	0.15159 (16)	0.89088 (10)	0.0415 (3)
H2	0.3490	0.2470	0.8830	0.050*
N3	0.25238 (15)	−0.02567 (16)	0.99381 (10)	0.0372 (3)
H3N	0.2705	−0.1020	0.9695	0.045*
N4	0.22253 (15)	0.22080 (16)	1.00973 (10)	0.0394 (3)
H4N	0.2267	0.3140	0.9987	0.047*
C1	0.38850 (19)	0.0537 (2)	0.83586 (12)	0.0383 (4)
C2	0.27105 (19)	0.11420 (19)	0.96112 (12)	0.0366 (4)
C3	0.19110 (17)	−0.00866 (19)	1.06892 (11)	0.0348 (4)
C4	0.1550 (2)	−0.1157 (2)	1.12841 (13)	0.0421 (4)
H4	0.1668	−0.2207	1.1213	0.051*
C5	0.1006 (2)	−0.0573 (2)	1.19897 (14)	0.0475 (4)
H5	0.0780	−0.1248	1.2418	0.057*
C6	0.0785 (2)	0.1001 (2)	1.20790 (14)	0.0487 (4)
H6	0.0397	0.1343	1.2556	0.058*
C7	0.11296 (19)	0.2059 (2)	1.14772 (13)	0.0445 (4)
H7	0.0972	0.3106	1.1531	0.053*
C8	0.17212 (18)	0.14874 (18)	1.07901 (12)	0.0360 (4)
O1	0.44295 (16)	0.44905 (15)	0.86287 (10)	0.0522 (3)
H1O	0.5262	0.4440	0.9042	0.078*
H2O	0.3841	0.4980	0.8881	0.078*
Cl1	0.23786 (6)	0.57314 (5)	0.98063 (4)	0.05321 (17)

	U11	U22	U33	U12	U13	U23
S1	0.0756 (4)	0.0303 (3)	0.0653 (3)	−0.0048 (2)	0.0406 (3)	−0.0053 (2)
N1	0.0621 (10)	0.0372 (8)	0.0539 (9)	−0.0004 (7)	0.0303 (8)	0.0037 (7)
N2	0.0569 (9)	0.0264 (7)	0.0446 (8)	−0.0004 (6)	0.0210 (7)	0.0028 (6)
N3	0.0462 (8)	0.0258 (7)	0.0404 (7)	0.0011 (6)	0.0152 (6)	−0.0025 (6)
N4	0.0479 (8)	0.0243 (7)	0.0456 (8)	0.0015 (6)	0.0150 (6)	0.0010 (6)
C1	0.0400 (9)	0.0361 (9)	0.0372 (8)	−0.0004 (7)	0.0104 (7)	0.0009 (7)
C2	0.0411 (9)	0.0288 (8)	0.0372 (8)	0.0000 (7)	0.0092 (7)	0.0006 (7)
C3	0.0347 (8)	0.0307 (8)	0.0371 (8)	0.0004 (6)	0.0094 (7)	−0.0016 (7)
C4	0.0455 (9)	0.0320 (9)	0.0489 (10)	0.0001 (7)	0.0156 (8)	0.0012 (7)
C5	0.0490 (10)	0.0459 (10)	0.0513 (11)	−0.0029 (8)	0.0214 (9)	0.0050 (8)
C6	0.0484 (10)	0.0511 (11)	0.0529 (11)	0.0017 (8)	0.0248 (9)	−0.0047 (9)
C7	0.0445 (10)	0.0356 (9)	0.0531 (10)	0.0049 (7)	0.0156 (8)	−0.0057 (8)
C8	0.0358 (8)	0.0313 (9)	0.0389 (9)	0.0001 (6)	0.0096 (7)	0.0001 (7)
O1	0.0616 (8)	0.0418 (7)	0.0558 (8)	0.0010 (6)	0.0227 (6)	−0.0045 (6)
Cl1	0.0654 (3)	0.0333 (3)	0.0646 (3)	0.0053 (2)	0.0264 (2)	0.0047 (2)

S1—C1	1.6673 (18)	C3—C4	1.386 (2)
N1—C1	1.319 (2)	C3—C8	1.395 (2)
N1—H1N	0.8607	C4—C5	1.382 (3)
N1—H2N	0.8592	C4—H4	0.9300
N2—C2	1.359 (2)	C5—C6	1.397 (3)
N2—C1	1.387 (2)	C5—H5	0.9300
N2—H2	0.8606	C6—C7	1.379 (3)
N3—C2	1.339 (2)	C6—H6	0.9300
N3—C3	1.396 (2)	C7—C8	1.382 (2)
N3—H3N	0.7964	C7—H7	0.9300
N4—C2	1.332 (2)	O1—H1O	0.8112
N4—C8	1.393 (2)	O1—H2O	0.8651
N4—H4N	0.8304
C1—N1—H1N	121.3	C4—C3—N3	131.46 (15)
C1—N1—H2N	120.4	C8—C3—N3	106.54 (14)
H1N—N1—H2N	118.4	C5—C4—C3	116.06 (16)
C2—N2—C1	128.15 (14)	C5—C4—H4	122.0
C2—N2—H2	118.3	C3—C4—H4	122.0
C1—N2—H2	113.1	C4—C5—C6	122.05 (18)
C2—N3—C3	108.39 (14)	C4—C5—H5	119.0
C2—N3—H3N	122.0	C6—C5—H5	119.0
C3—N3—H3N	129.5	C7—C6—C5	121.59 (17)
C2—N4—C8	108.90 (13)	C7—C6—H6	119.2
C2—N4—H4N	122.2	C5—C6—H6	119.2
C8—N4—H4N	128.9	C6—C7—C8	116.69 (17)
N1—C1—N2	113.04 (15)	C6—C7—H7	121.7
N1—C1—S1	123.02 (14)	C8—C7—H7	121.7
N2—C1—S1	123.94 (13)	C7—C8—N4	132.05 (15)
N4—C2—N3	109.79 (15)	C7—C8—C3	121.58 (16)
N4—C2—N2	121.94 (15)	N4—C8—C3	106.37 (14)
N3—C2—N2	128.26 (15)	H1O—O1—H2O	107.1
C4—C3—C8	121.98 (16)
C2—N2—C1—N1	−174.63 (16)	C3—C4—C5—C6	2.0 (3)
C2—N2—C1—S1	5.7 (3)	C4—C5—C6—C7	−1.3 (3)
C8—N4—C2—N3	1.18 (19)	C5—C6—C7—C8	−0.8 (3)
C8—N4—C2—N2	−177.76 (15)	C6—C7—C8—N4	−177.98 (17)
C3—N3—C2—N4	−1.16 (18)	C6—C7—C8—C3	2.1 (2)
C3—N3—C2—N2	177.68 (16)	C2—N4—C8—C7	179.38 (17)
C1—N2—C2—N4	178.93 (15)	C2—N4—C8—C3	−0.71 (18)
C1—N2—C2—N3	0.2 (3)	C4—C3—C8—C7	−1.5 (3)
C2—N3—C3—C4	−177.73 (17)	N3—C3—C8—C7	179.93 (15)
C2—N3—C3—C8	0.69 (18)	C4—C3—C8—N4	178.62 (15)
C8—C3—C4—C5	−0.6 (2)	N3—C3—C8—N4	0.01 (17)
N3—C3—C4—C5	177.59 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···Cl1i	0.81	2.29	3.0991 (15)	179
O1—H2O···Cl1	0.87	2.30	3.1443 (14)	165
N1—H1N···O1	0.86	2.32	3.064 (2)	145
N1—H2N···O1ii	0.86	2.14	3.000 (2)	174
N2—H2···O1	0.86	2.03	2.8667 (19)	165
N3—H3N···S1	0.80	2.43	3.0146 (14)	131
N4—H4N···Cl1	0.83	2.28	3.1055 (15)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯Cl1i	0.81	2.29	3.0991 (15)	179
O1—H2O⋯Cl1	0.87	2.30	3.1443 (14)	165
N1—H1N⋯O1	0.86	2.32	3.064 (2)	145
N1—H2N⋯O1ii	0.86	2.14	3.000 (2)	174
N2—H2⋯O1	0.86	2.03	2.8667 (19)	165
N3—H3N⋯S1	0.80	2.43	3.0146 (14)	131
N4—H4N⋯Cl1	0.83	2.28	3.1055 (15)	175

Symmetry codes: (i) ; (ii) .