3,3′-[1,4-Phenyl­enebis(methyl­ene)]­bis­(1-propyl­benzimidazolium) dichloride dihydrate

Haque, R.A.; Iqbal, M.A.; Ahmad, S.A.; Chia, T.S.; Fun, H.-K.

doi:10.1107/S1600536812007738

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o845-o846

doi:10.1107/S1600536812007738

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3,3′-[1,4-Phenylenebis(methylene)]bis(1-propylbenzimidazolium) dichloride dihydrate

Rosenani A. Haque,^a Muhammad Adnan Iqbal,^a Safaa A. Ahmad,^b Tze Shyang Chia ^c and Hoong-Kun Fun ^c ^*‡

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Chemistry, College of Education Samarra, University of Tikrit, Tikrit 43001, Iraq, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 18 February 2012; accepted 21 February 2012; online 24 February 2012)

The asymmetric unit of the title compound, C₂₈H₃₂N₄²⁺·2Cl⁻·2H₂O, contains half of a 3,3′-[1,4-phenylenebis(methylene)]bis(1-propylbenzimidazolium) cation, one chloride anion and one water molecule. 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 molecules 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 interactions, 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

C₂₈H₃₂N₄²⁺·2Cl⁻·2H₂O
M_r = 531.51
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.061
wR(F²) = 0.196
S = 1.08
3085 reflections
172 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.86 e Å⁻³
Δρ_min = −0.48 e Å⁻³

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) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812007738/is5076sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812007738/is5076Isup3.cml

checkCIF report

Comment top

Benzimidazole constituted compounds have diverse biological and clinical applications (Narasimhan et al., 2012). Previously, we have reported crystal structures of ortho-xylyl linked bis-benzimidazolium salts with heptyl (Haque et al., 2011), propyl (Iqbal et al., 2012), and ethyl (Haque et al., 2012) substitutions. In this report, we describe the crystal structure of a para-xylyl linked bis-benzimidazolium salt with propyl substitutions.

The molecular structure of the title compound is shown in Fig. 1. The asymmetric unit of the title compound, C₂₈H₃₂N₄²⁺.2Cl^-.2H₂O, consists of one half-molecule of 3,3'-[1,4-phenylenebis(methylene)]bis(1-propyl-benzimidazolium) cation, one chlorine anion and one water molecule. The complete cation is generated by a crystallographic inversion center (-x, -y + 2, -z). The central benzene ring (C1–C3/C1A–C3A) forms a dihedral angle of 66.06 (11)° with its adjacent benzimidazolium ring (N1/N2/C5–C11) [maximum deviation = 0.031 (2) Å at atom C5]. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Haque et al., 2011,2012; Iqbal et al., 2012).

In the crystal structure, (Fig. 2), the cations, anions and water molecules are linked by intermolecular O1W—H1W1···Cl1, O1W—H2W1···Cl1, C1—H1A···Cl1, C4—H4B···Cl1, C6—H6A···Cl1, C11—H11A···O1W, C12—H12A···Cl1, and C12—H12B···Cl1 hydrogen bonds (Table 1) into a three-dimensional network. The crystal packing is further stabilized by π–π interactions with Cg1···Cg3 (1-x, 1-y, -z) distance = 3.5561 (15) Å and Cg3···Cg3 (1-x, 1-y, -z) distance = 3.6708 (15) Å, where Cg1 and Cg3 are the centroids of N1/N2/C5/C10/C11 and C5–C10 rings, respectively.

Related literature top

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 top

A mixture of benzimidazole (2.95 g, 25 mmol) and finely ground potassium hydroxide (2.36 g, 30 mmol) in 30 ml of DMSO was stirred at room temperature (27–28 °C) for 30 min. 1-Bromopropane (2.27 ml, 25 mmol) was added drop-wise into this consistently stirred mixture with further stirring for 2 h at the same temperature. The mixture was then poured into water (400 ml) and was extracted by chloroform (5 x 20 ml). The extract was dried by magnesium sulfate and evaporated under reduced pressure to get N-ethylbenzimidazole (1) as a thick yellowish fluid. Furthermore, a mixture of 1 (1.60 g, 10 mmol) and 1,4-bis(chloromethyl)benzene (0.88 g, 5 mmol) in dioxane (30 ml) was refluxed at 100 °C for 18 h. This desired compound (2.2Cl) appeared as white precipitates in the light brown solution. The mixture was filtered and the precipitates were washed with fresh dioxane (3 × 5 ml), dried at room temperature for 24 h, and the soft lumps obtained were ground into a fine powder (2.15 g, 87%). Saturated solution of 2.2Cl in methanol (0.5 ml) was exposed to diethyl ether vapours (vapour diffusion) at room temperature overnight to get single crystals suitable for X-ray diffraction study.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids. Atoms with suffix A were generated by symmetry code -x, -y + 2, -z.
	Fig. 2. The crystal packing of the title compound. Intermolecular hydrogen bonds are shown as dashed lines. H atoms not involved in the hydrogen bonds have been omitted for clarity.

3,3'-[1,4-Phenylenebis(methylene)]bis(1-propylbenzimidazolium) dichloride dihydrate top

Crystal data top

C₂₈H₃₂N₄²⁺·2Cl⁻·2H₂O	F(000) = 564
M_r = 531.51	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.1065P)² + 2.1866P] where P = (F_o² + 2F_c²)/3
3085 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.86 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

C₂₈H₃₂N₄²⁺·2Cl⁻·2H₂O	V = 1352.66 (14) Å³
M_r = 531.51	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.1177 (5) Å	µ = 0.27 mm⁻¹
b = 9.1042 (5) Å	T = 100 K
c = 18.3548 (11) Å	0.47 × 0.23 × 0.14 mm
β = 94.323 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3085 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2660 reflections with I > 2σ(I)
T_min = 0.882, T_max = 0.962	R_int = 0.053
11942 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.196	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.86 e Å⁻³
3085 reflections	Δρ_min = −0.48 e Å⁻³
172 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

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···Cl1^iv	0.99	2.75	3.740 (3)	175

Symmetry codes: (ii) −x+1, y+1/2, −z+1/2; (iii) x, −y+3/2, z−1/2; (iv) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₈H₃₂N₄²⁺·2Cl⁻·2H₂O
M_r	531.51
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	8.1177 (5), 9.1042 (5), 18.3548 (11)
β (°)	94.323 (2)
V (Å³)	1352.66 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.47 × 0.23 × 0.14

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.882, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	11942, 3085, 2660
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.196, 1.08
No. of reflections	3085
No. of parameters	172
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.86, −0.48

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+1, y+1/2, −z+1/2; (ii) x, −y+3/2, z−1/2; (iii) −x+1, y−1/2, −z+1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

RAH thanks Universiti Sains Malaysia (USM) for the Research University (RU) grants Nos. 1001/PKIMIA/811157 and 1001/PKIMIA/823082. MAI is grateful to (IPS) USM for financial support [fellowship USM.IPS/JWT/1/19 (JLD 6)] and a research attachment fund [P-KM0018/10(R) − 308/AIPS/415401]. HKF and TSC thank USM for the RU grant No. 1001/PFIZIK/811160. TSC thanks the Malaysian Government and USM for the award of the post of Research Officer under the RU grant No. 1001/PSKBP/8630013.

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