2-(3-Pyridinio)benzimidazolium penta-chloridoanti-monate(III) monohydrate.

In the title compound, (C(12)H(11)N(3))[SbCl(5)]·H(2)O, the Sb(III) centre is surrounded by five Cl atoms and displays a distorted square-pyramidal coordination geometry. The dihedral angle formed by the plane of the imidazole ring system with the pyridine ring is 4.380 (15)°. The crystal structure is stabilized by N-H⋯Cl, O-H⋯Cl and N-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For the pharmacologic activity of benzimidazole derivatives, see: Minoura et al. (2004 ▶); Pawar et al. (2004 ▶); Demirayak et al. (2002 ▶).

Experimental

Crystal data

(C12H11N3)[SbCl5]·H2O

M = 514.25

Monoclinic,

a = 9.2619 (19) Å

b = 13.425 (3) Å

c = 14.380 (3) Å

β = 102.27 (3)°

V = 1747.2 (7) Å3

Z = 4

Mo Kα radiation

μ = 2.35 mm−1

T = 293 K

0.25 × 0.22 × 0.19 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.892, T max = 0.964 (expected range = 0.592–0.640)

15623 measured reflections

3410 independent reflections

3037 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.068

S = 0.93

3410 reflections

199 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.48 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018935/rz2324sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018935/rz2324Isup2.hkl

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

(C12H11N3)[SbCl5]·H2O	F(000) = 1000
Mr = 514.25	Dx = 1.955 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1647 reflections
a = 9.2619 (19) Å	θ = 3.0–27.6°
b = 13.425 (3) Å	µ = 2.35 mm−1
c = 14.380 (3) Å	T = 293 K
β = 102.27 (3)°	Prism, colourless
V = 1747.2 (7) Å3	0.25 × 0.22 × 0.19 mm
Z = 4

Rigaku SCXmini diffractometer	3410 independent reflections
Radiation source: fine-focus sealed tube	3037 reflections with I > 2σ(I)
graphite	Rint = 0.043
Detector resolution: 13.6612 pixels mm-1	θmax = 26.0°, θmin = 3.0°
ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −16→16
Tmin = 0.892, Tmax = 0.964	l = −17→17
15623 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.0319P)2 + 2.5497P] where P = (Fo2 + 2Fc2)/3
3410 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.32 e Å−3
6 restraints	Δρmin = −0.47 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
Sb1	0.98691 (2)	0.410246 (16)	0.112742 (15)	0.02964 (9)
Cl1	0.98813 (10)	0.24807 (7)	0.17778 (7)	0.0451 (2)
Cl2	1.06091 (10)	0.48665 (7)	0.29163 (6)	0.0446 (2)
Cl3	0.93983 (10)	0.34774 (8)	−0.06139 (6)	0.0445 (2)
Cl4	1.25689 (10)	0.38926 (8)	0.11321 (8)	0.0516 (3)
Cl5	0.68651 (10)	0.39170 (8)	0.09585 (6)	0.0434 (2)
C1	0.5091 (3)	0.3717 (2)	0.4685 (2)	0.0280 (7)
C2	0.4622 (4)	0.3711 (3)	0.3703 (2)	0.0346 (7)
H2A	0.3631	0.3642	0.3409	0.042*
C3	0.5715 (4)	0.3813 (3)	0.3187 (3)	0.0412 (9)
H3A	0.5457	0.3804	0.2526	0.049*
C4	0.7199 (4)	0.3929 (3)	0.3638 (3)	0.0463 (10)
H4A	0.7901	0.3989	0.3265	0.056*
C5	0.7658 (4)	0.3958 (3)	0.4611 (3)	0.0433 (9)
H5A	0.8646	0.4046	0.4905	0.052*
C6	0.6566 (4)	0.3849 (2)	0.5131 (2)	0.0304 (7)
C7	0.5252 (3)	0.3714 (2)	0.6244 (2)	0.0280 (7)
C8	0.4838 (4)	0.3694 (2)	0.7169 (2)	0.0289 (7)
C9	0.5913 (4)	0.3773 (3)	0.7992 (2)	0.0376 (8)
H9A	0.6906	0.3812	0.7963	0.045*
N3	0.5509 (4)	0.3794 (2)	0.8830 (2)	0.0421 (7)
H3B	0.6190	0.3841	0.9338	0.051*
C11	0.4115 (5)	0.3745 (3)	0.8920 (3)	0.0417 (9)
H11A	0.3891	0.3776	0.9520	0.050*
C12	0.3373 (4)	0.3627 (3)	0.7250 (2)	0.0364 (8)
H12A	0.2630	0.3566	0.6705	0.044*
N1	0.4320 (3)	0.3631 (2)	0.54084 (18)	0.0285 (6)
H1A	0.3383	0.3538	0.5328	0.034*
N2	0.6611 (3)	0.3840 (2)	0.6097 (2)	0.0335 (6)
H2B	0.7396	0.3905	0.6536	0.040*
C10	0.3011 (4)	0.3649 (3)	0.8128 (3)	0.0407 (8)
H10A	0.2031	0.3599	0.8182	0.049*
O1W	0.1429 (3)	0.3470 (2)	0.4754 (2)	0.0636 (9)
H1WA	0.1260	0.3892	0.4303	0.076*
H1WB	0.0951	0.2925	0.4676	0.076*

	U11	U22	U33	U12	U13	U23
Sb1	0.02958 (13)	0.02996 (14)	0.02782 (13)	−0.00150 (9)	0.00262 (9)	0.00183 (9)
Cl1	0.0391 (5)	0.0362 (5)	0.0563 (6)	−0.0002 (4)	0.0014 (4)	0.0136 (4)
Cl2	0.0442 (5)	0.0505 (5)	0.0366 (5)	−0.0094 (4)	0.0033 (4)	−0.0069 (4)
Cl3	0.0465 (5)	0.0524 (6)	0.0302 (4)	0.0073 (4)	−0.0016 (4)	−0.0029 (4)
Cl4	0.0338 (5)	0.0687 (7)	0.0536 (6)	−0.0061 (4)	0.0121 (4)	−0.0013 (5)
Cl5	0.0362 (5)	0.0638 (6)	0.0294 (4)	0.0076 (4)	0.0051 (4)	−0.0009 (4)
C1	0.0268 (16)	0.0268 (16)	0.0303 (17)	−0.0023 (13)	0.0056 (13)	0.0006 (13)
C2	0.0346 (18)	0.0373 (19)	0.0307 (17)	−0.0029 (15)	0.0042 (14)	0.0015 (15)
C3	0.050 (2)	0.041 (2)	0.0347 (19)	0.0018 (17)	0.0125 (17)	0.0028 (16)
C4	0.043 (2)	0.052 (2)	0.050 (2)	0.0057 (18)	0.0234 (19)	0.0063 (18)
C5	0.0252 (18)	0.054 (2)	0.052 (2)	0.0025 (16)	0.0107 (16)	−0.0012 (18)
C6	0.0258 (16)	0.0304 (17)	0.0345 (18)	0.0018 (13)	0.0051 (14)	0.0005 (14)
C7	0.0243 (16)	0.0278 (16)	0.0296 (17)	−0.0012 (13)	0.0003 (13)	0.0004 (13)
C8	0.0297 (16)	0.0262 (16)	0.0284 (16)	−0.0001 (13)	0.0011 (13)	0.0001 (13)
C9	0.0345 (19)	0.042 (2)	0.0316 (18)	−0.0054 (15)	−0.0032 (15)	−0.0015 (15)
N3	0.0470 (19)	0.0465 (19)	0.0260 (15)	−0.0043 (14)	−0.0073 (13)	−0.0020 (13)
C11	0.056 (2)	0.039 (2)	0.0301 (19)	−0.0013 (17)	0.0093 (17)	−0.0027 (16)
C12	0.0316 (18)	0.043 (2)	0.0312 (18)	−0.0028 (15)	−0.0005 (14)	0.0018 (15)
N1	0.0199 (13)	0.0392 (16)	0.0252 (13)	−0.0065 (11)	0.0026 (10)	0.0025 (12)
N2	0.0215 (13)	0.0430 (17)	0.0331 (15)	−0.0011 (12)	−0.0008 (11)	−0.0007 (13)
C10	0.039 (2)	0.048 (2)	0.0365 (19)	−0.0003 (17)	0.0103 (16)	−0.0029 (17)
O1W	0.0352 (15)	0.074 (2)	0.073 (2)	−0.0205 (14)	−0.0072 (14)	0.0269 (17)

Sb1—Cl1	2.3687 (10)	C7—N1	1.327 (4)
Sb1—Cl4	2.5149 (11)	C7—C8	1.461 (4)
Sb1—Cl3	2.5885 (10)	C8—C9	1.379 (5)
Sb1—Cl2	2.7184 (11)	C8—C12	1.389 (5)
Sb1—Cl5	2.7522 (11)	C9—N3	1.336 (5)
C1—C2	1.386 (5)	C9—H9A	0.9300
C1—N1	1.387 (4)	N3—C11	1.327 (5)
C1—C6	1.391 (4)	N3—H3B	0.8600
C2—C3	1.383 (5)	C11—C10	1.365 (5)
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.398 (6)	C12—C10	1.374 (5)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.374 (6)	N1—H1A	0.8600
C4—H4A	0.9300	N2—H2B	0.8600
C5—C6	1.388 (5)	C10—H10A	0.9300
C5—H5A	0.9300	O1W—H1WA	0.8501
C6—N2	1.381 (4)	O1W—H1WB	0.8499
C7—N2	1.331 (4)
Cl1—Sb1—Cl4	88.55 (4)	N2—C7—N1	108.8 (3)
Cl1—Sb1—Cl3	93.99 (4)	N2—C7—C8	126.0 (3)
Cl4—Sb1—Cl3	85.94 (4)	N1—C7—C8	125.2 (3)
Cl1—Sb1—Cl2	89.66 (4)	C9—C8—C12	118.3 (3)
Cl4—Sb1—Cl2	89.38 (4)	C9—C8—C7	119.8 (3)
Cl3—Sb1—Cl2	173.98 (3)	C12—C8—C7	121.8 (3)
Cl1—Sb1—Cl5	82.62 (3)	N3—C9—C8	119.0 (3)
Cl4—Sb1—Cl5	167.42 (4)	N3—C9—H9A	120.5
Cl3—Sb1—Cl5	85.76 (4)	C8—C9—H9A	120.5
Cl2—Sb1—Cl5	99.46 (4)	C11—N3—C9	123.5 (3)
C2—C1—N1	131.6 (3)	C11—N3—H3B	118.2
C2—C1—C6	122.4 (3)	C9—N3—H3B	118.2
N1—C1—C6	106.0 (3)	N3—C11—C10	119.7 (3)
C3—C2—C1	116.0 (3)	N3—C11—H11A	120.2
C3—C2—H2A	122.0	C10—C11—H11A	120.2
C1—C2—H2A	122.0	C10—C12—C8	120.6 (3)
C2—C3—C4	121.5 (4)	C10—C12—H12A	119.7
C2—C3—H3A	119.3	C8—C12—H12A	119.7
C4—C3—H3A	119.3	C7—N1—C1	109.4 (3)
C5—C4—C3	122.4 (4)	C7—N1—H1A	125.3
C5—C4—H4A	118.8	C1—N1—H1A	125.3
C3—C4—H4A	118.8	C7—N2—C6	109.5 (3)
C4—C5—C6	116.2 (3)	C7—N2—H2B	125.3
C4—C5—H5A	121.9	C6—N2—H2B	125.3
C6—C5—H5A	121.9	C11—C10—C12	118.9 (4)
N2—C6—C5	132.3 (3)	C11—C10—H10A	120.5
N2—C6—C1	106.3 (3)	C12—C10—H10A	120.5
C5—C6—C1	121.4 (3)	H1WA—O1W—H1WB	117.8

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1W	0.86	1.82	2.652 (4)	161
N3—H3B···Cl5i	0.86	2.28	3.056 (3)	150
N2—H2B···Cl2ii	0.86	2.48	3.179 (3)	139
O1W—H1WA···Cl2iii	0.85	2.35	3.197 (3)	172
O1W—H1WB···Cl3iv	0.85	2.35	3.198 (3)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1W	0.86	1.82	2.652 (4)	161
N3—H3B⋯Cl5i	0.86	2.28	3.056 (3)	150
N2—H2B⋯Cl2ii	0.86	2.48	3.179 (3)	139
O1W—H1WA⋯Cl2iii	0.85	2.35	3.197 (3)	172
O1W—H1WB⋯Cl3iv	0.85	2.35	3.198 (3)	174

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .