3,3'-[1,4-Phenyl-enebis(methyl-ene)]-bis-(1-propyl-benzimidazolium) dichloride dihydrate.

The asymmetric unit of the title compound, C(28)H(32)N(4) (2+)·2Cl(-)·2H(2)O, contains half of a 3,3'-[1,4-phenyl-enebis(methyl-ene)]bis-(1-propyl-benzimidazolium) cation, one chloride anion and one water mol-ecule. The complete cation is generated by a crystallographic inversion center. The central benzene ring forms a dihedral angle of 66.06 (11)° with its adjacent benzimidazolium ring system. In the crystal, the cations, anions and water mol-ecules are linked by O-H⋯Cl, C-H⋯O and C-H⋯Cl hydrogen bonds into a three-dimensional network. The crystal packing is further stabilized by π-π inter-actions, with centroid-centroid distances of 3.5561 (15) and 3.6708 (15) Å.

Related literature

For details and applications of benzimidazole derivatives, see: Narasimhan et al. (2012 ▶). For related structures, see: Haque et al. (2011 ▶, 2012 ▶); Iqbal et al. (2012 ▶). For reference bond lengths, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C28H32N4 2+·2Cl−·2H2O

M = 531.51

Monoclinic,

a = 8.1177 (5) Å

b = 9.1042 (5) Å

c = 18.3548 (11) Å

β = 94.323 (2)°

V = 1352.66 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.27 mm−1

T = 100 K

0.47 × 0.23 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.882, T max = 0.962

11942 measured reflections

3085 independent reflections

2660 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.196

S = 1.08

3085 reflections

172 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.86 e Å−3

Δρmin = −0.48 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812007738/is5076sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007738/is5076Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007738/is5076Isup3.cml

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

C28H32N42+·2Cl−·2H2O	F(000) = 564
Mr = 531.51	Dx = 1.305 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5809 reflections
a = 8.1177 (5) Å	θ = 2.5–32.5°
b = 9.1042 (5) Å	µ = 0.27 mm−1
c = 18.3548 (11) Å	T = 100 K
β = 94.323 (2)°	Block, colourless
V = 1352.66 (14) Å3	0.47 × 0.23 × 0.14 mm
Z = 2

Bruker SMART APEXII CCD area-detector diffractometer	3085 independent reflections
Radiation source: fine-focus sealed tube	2660 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
φ and ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.882, Tmax = 0.962	k = −11→11
11942 measured reflections	l = −22→23

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.196	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.1065P)2 + 2.1866P] where P = (Fo2 + 2Fc2)/3
3085 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.86 e Å−3
0 restraints	Δρmin = −0.48 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Cl1	0.45230 (8)	0.59270 (7)	0.33489 (4)	0.0240 (2)
O1W	0.3206 (3)	0.8654 (3)	0.23712 (12)	0.0269 (5)
N1	0.2941 (3)	0.6933 (2)	0.04689 (12)	0.0175 (5)
N2	0.2605 (3)	0.4951 (2)	0.11124 (12)	0.0179 (5)
C1	0.0921 (3)	0.9600 (3)	−0.05784 (15)	0.0201 (5)
H1A	0.1549	0.9329	−0.0974	0.024*
C2	0.1507 (3)	0.9274 (3)	0.01358 (15)	0.0175 (5)
C3	0.0581 (3)	0.9677 (3)	0.07154 (15)	0.0201 (5)
H3A	0.0977	0.9458	0.1203	0.024*
C4	0.3152 (3)	0.8500 (3)	0.02876 (15)	0.0206 (5)
H4A	0.3796	0.8579	−0.0148	0.025*
H4B	0.3786	0.8994	0.0699	0.025*
C5	0.2927 (3)	0.5759 (3)	−0.00194 (15)	0.0170 (5)
C6	0.3152 (3)	0.5696 (3)	−0.07626 (15)	0.0194 (5)
H6A	0.3306	0.6557	−0.1042	0.023*
C7	0.3140 (3)	0.4312 (3)	−0.10732 (15)	0.0199 (5)
H7A	0.3285	0.4223	−0.1580	0.024*
C8	0.2918 (3)	0.3032 (3)	−0.06619 (15)	0.0206 (5)
H8A	0.2917	0.2104	−0.0898	0.025*
C9	0.2701 (3)	0.3095 (3)	0.00817 (15)	0.0199 (5)
H9A	0.2553	0.2235	0.0362	0.024*
C10	0.2715 (3)	0.4492 (3)	0.03924 (14)	0.0172 (5)
C11	0.2750 (3)	0.6401 (3)	0.11360 (15)	0.0197 (5)
H11A	0.2722	0.6979	0.1566	0.024*
C12	0.2412 (3)	0.3977 (3)	0.17406 (14)	0.0197 (5)
H12A	0.2731	0.4515	0.2198	0.024*
H12B	0.3164	0.3125	0.1713	0.024*
C13	0.0641 (3)	0.3427 (3)	0.17592 (14)	0.0208 (5)
H13A	0.0267	0.3006	0.1278	0.025*
H13B	−0.0093	0.4262	0.1856	0.025*
C14	0.0517 (4)	0.2262 (3)	0.23502 (16)	0.0276 (6)
H14A	−0.0607	0.1865	0.2324	0.041*
H14B	0.0779	0.2705	0.2832	0.041*
H14C	0.1301	0.1468	0.2274	0.041*
H1W1	0.377 (6)	0.792 (5)	0.264 (2)	0.050 (12)*
H2W1	0.392 (6)	0.920 (5)	0.220 (2)	0.046 (12)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0237 (4)	0.0186 (4)	0.0300 (4)	−0.0012 (2)	0.0043 (3)	−0.0029 (2)
O1W	0.0269 (11)	0.0265 (12)	0.0276 (11)	−0.0050 (9)	0.0037 (8)	−0.0007 (9)
N1	0.0159 (10)	0.0109 (10)	0.0254 (11)	0.0014 (8)	0.0009 (8)	−0.0022 (8)
N2	0.0163 (10)	0.0152 (11)	0.0219 (11)	0.0002 (8)	0.0001 (8)	−0.0025 (8)
C1	0.0189 (12)	0.0129 (12)	0.0289 (14)	−0.0010 (9)	0.0052 (10)	−0.0004 (10)
C2	0.0162 (11)	0.0066 (11)	0.0300 (14)	−0.0004 (8)	0.0041 (9)	−0.0003 (9)
C3	0.0210 (12)	0.0111 (12)	0.0281 (13)	−0.0007 (9)	0.0024 (10)	−0.0003 (10)
C4	0.0173 (12)	0.0119 (12)	0.0328 (14)	0.0002 (9)	0.0032 (10)	0.0003 (10)
C5	0.0116 (11)	0.0110 (12)	0.0280 (13)	0.0000 (8)	−0.0012 (9)	−0.0017 (9)
C6	0.0154 (12)	0.0143 (12)	0.0281 (14)	−0.0004 (9)	−0.0010 (9)	0.0032 (10)
C7	0.0184 (12)	0.0169 (13)	0.0242 (13)	−0.0016 (9)	−0.0004 (9)	−0.0020 (10)
C8	0.0204 (12)	0.0159 (13)	0.0251 (13)	−0.0017 (10)	−0.0010 (9)	−0.0038 (10)
C9	0.0171 (11)	0.0124 (12)	0.0301 (14)	−0.0004 (9)	0.0013 (9)	0.0013 (10)
C10	0.0122 (11)	0.0168 (13)	0.0224 (13)	0.0013 (9)	−0.0010 (9)	−0.0009 (10)
C11	0.0142 (11)	0.0191 (13)	0.0257 (13)	0.0028 (9)	0.0001 (9)	−0.0029 (10)
C12	0.0186 (12)	0.0179 (13)	0.0223 (13)	0.0027 (9)	−0.0013 (9)	0.0042 (10)
C13	0.0175 (12)	0.0221 (14)	0.0227 (13)	0.0023 (10)	0.0017 (9)	−0.0001 (10)
C14	0.0257 (14)	0.0284 (16)	0.0291 (15)	0.0031 (11)	0.0054 (11)	0.0054 (12)

O1W—H1W1	0.93 (5)	C6—C7	1.382 (4)
O1W—H2W1	0.84 (5)	C6—H6A	0.9500
N1—C11	1.337 (3)	C7—C8	1.407 (4)
N1—C5	1.395 (3)	C7—H7A	0.9500
N1—C4	1.478 (3)	C8—C9	1.390 (4)
N2—C11	1.326 (4)	C8—H8A	0.9500
N2—C10	1.395 (3)	C9—C10	1.393 (4)
N2—C12	1.472 (3)	C9—H9A	0.9500
C1—C3i	1.392 (4)	C11—H11A	0.9500
C1—C2	1.393 (4)	C12—C13	1.526 (4)
C1—H1A	0.9500	C12—H12A	0.9900
C2—C3	1.397 (4)	C12—H12B	0.9900
C2—C4	1.517 (3)	C13—C14	1.526 (4)
C3—C1i	1.392 (4)	C13—H13A	0.9900
C3—H3A	0.9500	C13—H13B	0.9900
C4—H4A	0.9900	C14—H14A	0.9800
C4—H4B	0.9900	C14—H14B	0.9800
C5—C6	1.391 (4)	C14—H14C	0.9800
C5—C10	1.397 (4)
H1W1—O1W—H2W1	107 (4)	C9—C8—C7	121.6 (2)
C11—N1—C5	108.4 (2)	C9—C8—H8A	119.2
C11—N1—C4	125.4 (2)	C7—C8—H8A	119.2
C5—N1—C4	126.2 (2)	C8—C9—C10	116.2 (2)
C11—N2—C10	108.5 (2)	C8—C9—H9A	121.9
C11—N2—C12	126.1 (2)	C10—C9—H9A	121.9
C10—N2—C12	125.4 (2)	C9—C10—N2	131.5 (2)
C3i—C1—C2	120.2 (2)	C9—C10—C5	122.0 (2)
C3i—C1—H1A	119.9	N2—C10—C5	106.5 (2)
C2—C1—H1A	119.9	N2—C11—N1	110.3 (2)
C1—C2—C3	119.7 (2)	N2—C11—H11A	124.8
C1—C2—C4	120.4 (2)	N1—C11—H11A	124.8
C3—C2—C4	119.9 (2)	N2—C12—C13	111.8 (2)
C1i—C3—C2	120.1 (3)	N2—C12—H12A	109.3
C1i—C3—H3A	120.0	C13—C12—H12A	109.3
C2—C3—H3A	120.0	N2—C12—H12B	109.3
N1—C4—C2	112.0 (2)	C13—C12—H12B	109.3
N1—C4—H4A	109.2	H12A—C12—H12B	107.9
C2—C4—H4A	109.2	C12—C13—C14	110.9 (2)
N1—C4—H4B	109.2	C12—C13—H13A	109.5
C2—C4—H4B	109.2	C14—C13—H13A	109.5
H4A—C4—H4B	107.9	C12—C13—H13B	109.5
C6—C5—N1	131.8 (2)	C14—C13—H13B	109.5
C6—C5—C10	121.8 (2)	H13A—C13—H13B	108.1
N1—C5—C10	106.3 (2)	C13—C14—H14A	109.5
C7—C6—C5	116.4 (2)	C13—C14—H14B	109.5
C7—C6—H6A	121.8	H14A—C14—H14B	109.5
C5—C6—H6A	121.8	C13—C14—H14C	109.5
C6—C7—C8	122.0 (2)	H14A—C14—H14C	109.5
C6—C7—H7A	119.0	H14B—C14—H14C	109.5
C8—C7—H7A	119.0
C3i—C1—C2—C3	−0.1 (4)	C8—C9—C10—N2	−177.0 (2)
C3i—C1—C2—C4	−179.4 (2)	C8—C9—C10—C5	0.2 (4)
C1—C2—C3—C1i	0.1 (4)	C11—N2—C10—C9	177.2 (3)
C4—C2—C3—C1i	179.4 (2)	C12—N2—C10—C9	−1.1 (4)
C11—N1—C4—C2	−86.9 (3)	C11—N2—C10—C5	−0.3 (3)
C5—N1—C4—C2	94.0 (3)	C12—N2—C10—C5	−178.6 (2)
C1—C2—C4—N1	−103.9 (3)	C6—C5—C10—C9	−0.6 (4)
C3—C2—C4—N1	76.9 (3)	N1—C5—C10—C9	−177.7 (2)
C11—N1—C5—C6	−176.6 (3)	C6—C5—C10—N2	177.2 (2)
C4—N1—C5—C6	2.6 (4)	N1—C5—C10—N2	0.1 (3)
C11—N1—C5—C10	0.1 (3)	C10—N2—C11—N1	0.3 (3)
C4—N1—C5—C10	179.3 (2)	C12—N2—C11—N1	178.6 (2)
N1—C5—C6—C7	176.8 (2)	C5—N1—C11—N2	−0.3 (3)
C10—C5—C6—C7	0.6 (4)	C4—N1—C11—N2	−179.5 (2)
C5—C6—C7—C8	−0.2 (4)	C11—N2—C12—C13	104.6 (3)
C6—C7—C8—C9	−0.1 (4)	C10—N2—C12—C13	−77.4 (3)
C7—C8—C9—C10	0.1 (4)	N2—C12—C13—C14	172.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···Cl1	0.93 (4)	2.29 (4)	3.200 (3)	166 (4)
O1W—H2W1···Cl1ii	0.84 (5)	2.30 (4)	3.130 (3)	170 (4)
C1—H1A···Cl1iii	0.95	2.81	3.677 (3)	153
C4—H4B···Cl1ii	0.99	2.77	3.741 (3)	167
C6—H6A···Cl1iii	0.95	2.76	3.691 (3)	165
C11—H11A···O1W	0.95	2.14	3.059 (4)	163
C12—H12A···Cl1	0.99	2.79	3.747 (3)	164
C12—H12B···Cl1iv	0.99	2.75	3.740 (3)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯Cl1	0.93 (4)	2.29 (4)	3.200 (3)	166 (4)
O1W—H2W1⋯Cl1i	0.84 (5)	2.30 (4)	3.130 (3)	170 (4)
C1—H1A⋯Cl1ii	0.95	2.81	3.677 (3)	153
C4—H4B⋯Cl1i	0.99	2.77	3.741 (3)	167
C6—H6A⋯Cl1ii	0.95	2.76	3.691 (3)	165
C11—H11A⋯O1W	0.95	2.14	3.059 (4)	163
C12—H12A⋯Cl1	0.99	2.79	3.747 (3)	164
C12—H12B⋯Cl1iii	0.99	2.75	3.740 (3)	175

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