3,3′-[1,2-Phenyl­enebis(methyl­ene)]bis­(1-heptyl­benzimidazolium) dibromide monohydrate

Haque, R.A.; Iqbal, M.A.; Hemamalini, M.; Fun, H.-K.

doi:10.1107/S1600536811023476

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Pages o1814-o1815

doi:10.1107/S1600536811023476

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3,3′-[1,2-Phenylenebis(methylene)]bis(1-heptylbenzimidazolium) dibromide monohydrate

Rosenani A. Haque,^a Muhammad Adnan Iqbal,^a Madhukar Hemamalini ^b and Hoong-Kun Fun ^b ^*‡

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 14 June 2011; accepted 16 June 2011; online 25 June 2011)

In the title salt, C₃₆H₄₈N₄²⁺·2Br⁻·H₂O, the central benzene ring makes dihedral angles of 84.77 (9) and 69.92 (7)° with the adjacent imidazole rings. In the crystal, one of the heptyl groups is disordered over two sets of sites with an occupancy ratio of 0.474 (5):0.526 (5). In the crystal, the cations, anions and water molecules are connected via intermolecular O—H⋯Br, C—H⋯Br and C—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For details and applications of N-heterocyclic carbenes (NHCs), see: Winkelmann & Navarro (2010 ); Kascatan-Nebioglu et al. (2007 ); Teyssot et al. (2009 ); Herrmann et al. (1995 ); Choi et al. (2001 ); Kumar & Kumar (2009 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₃₆H₄₈N₄²⁺·2Br⁻·H₂O
M_r = 714.62
Triclinic, $[P \overline 1]$
a = 8.8494 (1) Å
b = 14.7170 (3) Å
c = 16.0838 (2) Å
α = 115.705 (1)°
β = 105.380 (1)°
γ = 91.946 (1)°
V = 1792.83 (5) Å³
Z = 2
Mo Kα radiation
μ = 2.29 mm⁻¹
T = 100 K
0.39 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.469, T_max = 0.715
50860 measured reflections
12945 independent reflections
10091 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.077
S = 1.02
12945 reflections
442 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.84 e Å⁻³
Δρ_min = −0.75 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯Br1	0.84 (3)	2.50 (3)	3.3271 (17)	169 (2)
O1W—H2W1⋯Br2	0.79 (3)	2.54 (3)	3.3280 (14)	177 (3)
C1—H1A⋯Br1ⁱ	0.95	2.80	3.6093 (15)	144
C3—H3A⋯Br2ⁱⁱ	0.95	2.92	3.7866 (16)	153
C5—H5A⋯Br2ⁱⁱⁱ	0.95	2.89	3.8162 (17)	167
C8—H8A⋯Br2^iv	0.99	2.93	3.9117 (16)	172
C15—H15A⋯Br2^iv	0.99	2.72	3.6809 (19)	165
C15—H15B⋯Br1^iv	0.99	2.80	3.7842 (15)	170
C18—H18A⋯O1W^v	0.95	2.46	3.187 (2)	133
C20—H20A⋯Br2	0.95	2.76	3.6602 (16)	158
C22—H22A⋯Br1ⁱ	0.95	2.70	3.5577 (15)	150
C23—H23A⋯Br2ⁱ	0.99	2.89	3.7836 (14)	151
C23—H23B⋯Br2ⁱⁱ	0.99	2.81	3.7285 (17)	154
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x+1, y, z+1; (iii) x, y, z+1; (iv) -x, -y+1, -z+1; (v) x-1, y, z.

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/S1600536811023476/is2732sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811023476/is2732Isup2.hkl

checkCIF report

Comment top

N-Heterocyclic Carbenes (NHCs) is a versatile class of ligands, which have widespread applications in organometallic chemistry (Winkelmann & Navarro, 2010). Metal complexes of NHCs have proven to be potential antimicrobial (Kascatan-Nebioglu et al., 2007) and anticancer (Teyssot et al., 2009) agents. Notably, NHCs also exhibit excellent catalytical activity for Heck and Suzuki coupling reactions (Herrmann et al., 1995) and Metathesis Cross-Coupling reactions (Choi et al., 2001). Benzimidazole-based NHCs of similar structures and their metal complexes are now known to be effective catalysts for the cross coupling reactions of different alcohols and ratiometric sensing (Kumar & Kumar, 2009).

The asymmetric unit of the title compound, (Fig. 1), consists of a 3,3'-[1,2-phenylenebis(methylene)]bis(1-heptylbenzimidazolium) cation, two bromine anions and one water molecule. One of the heptyl group is disordered over two sets of sites, with an occupancy ratio of 0.474 (5):0.526 (5). The central benzene (C9–C14) ring makes dihedral angles of 84.77 (9) and 69.92 (7)° with the adjacent imidazole (N1/N2/C1/C2/C7) and (N3/N4/C16/C21/C22) rings, respectively.

In the crystal structure (Fig. 2), the cations, anions and water molecules are linked together via intermolecular O1W—H1W1···Br1, O1W—H2W1···Br2, C1—H1A···Br1, C3—H3A···Br2, C5—H5A···Br2, C8—H8A···Br2, C15—H15A···Br2, C15—H15B···Br1, C18—H18A···O1W, C20—H20A···Br2, C22—H22A···Br1, C23—H23A···Br2 and C23—H23B···Br2 (Table 1) hydrogen bonds, forming a three-dimensional network.

Related literature top

For details and applications of N-heterocyclic carbenes (NHCs), see: Winkelmann & Navarro (2010); Kascatan-Nebioglu et al. (2007); Teyssot et al. (2009); Herrmann et al. (1995); Choi et al. (2001); Kumar & Kumar (2009). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of benzimidazole (2.36 g, 20 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 minutes. 1-bromoheptane (3.14 ml, 20 mmol) was added drop-wise in this consistently stirred mixture with further stirring for 2 h at the same temperature, poured into water (300 ml) and was extracted by chloroform (5 × 20 ml). The extract was dried by magnesium sulphate and evaporated under reduced pressure to afford N-heptylbenzimidazole (1) as a thick yellowish fluid (3.87 g, 89.6%). Furthermore, a mixture of 1 (2.16 g, 10 mmol) and 1,2-bis(bromomethyl)benzene (1.32 g, 5 mmol) in dioxane (30 ml) was refluxed at 90 °C for 12 h. Desired compound (2.2Br) appeared as beige-colored precipitates in dark brown solution. The mixture was filtered and precipitates were washed by fresh dioxane (3 × 5 ml), dried at room temperature for 24 h, and soft lumps so obtained were ground to fine powder (1.72 g, 49.4%). Hot (saturated) solution of 2.2Br in deuterated DMSO (0.5 ml) was cooled to room temperature in NMR tube overnight to get single (prismatic) 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 asymmetric unit of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. H atoms have been omitted for clarity.
	Fig. 2. The crystal packing of the title compound, showing hydrogen-bonded (dashed lines) network.

3,3'-[1,2-Phenylenebis(methylene)]bis(1-heptylbenzimidazolium) dibromide monohydrate top

Crystal data top

C₃₆H₄₈N₄²⁺·2Br⁻·H₂O	Z = 2
M_r = 714.62	F(000) = 744
Triclinic, P1	D_x = 1.324 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8494 (1) Å	Cell parameters from 9922 reflections
b = 14.7170 (3) Å	θ = 2.6–33.7°
c = 16.0838 (2) Å	µ = 2.29 mm⁻¹
α = 115.705 (1)°	T = 100 K
β = 105.380 (1)°	Block, colourless
γ = 91.946 (1)°	0.39 × 0.18 × 0.16 mm
V = 1792.83 (5) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	12945 independent reflections
Radiation source: fine-focus sealed tube	10091 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 32.5°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
T_min = 0.469, T_max = 0.715	k = −22→22
50860 measured reflections	l = −24→24

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0359P)² + 0.6181P] where P = (F_o² + 2F_c²)/3
12945 reflections	(Δ/σ)_max = 0.001
442 parameters	Δρ_max = 0.84 e Å⁻³
9 restraints	Δρ_min = −0.75 e Å⁻³

Crystal data top

C₃₆H₄₈N₄²⁺·2Br⁻·H₂O	γ = 91.946 (1)°
M_r = 714.62	V = 1792.83 (5) Å³
Triclinic, P1	Z = 2
a = 8.8494 (1) Å	Mo Kα radiation
b = 14.7170 (3) Å	µ = 2.29 mm⁻¹
c = 16.0838 (2) Å	T = 100 K
α = 115.705 (1)°	0.39 × 0.18 × 0.16 mm
β = 105.380 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	12945 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	10091 reflections with I > 2σ(I)
T_min = 0.469, T_max = 0.715	R_int = 0.027
50860 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	9 restraints
wR(F²) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.84 e Å⁻³
12945 reflections	Δρ_min = −0.75 e Å⁻³
442 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 s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
Br1	0.365462 (16)	0.228743 (11)	0.219134 (10)	0.02173 (4)
Br2	0.031239 (16)	0.512483 (11)	0.193441 (10)	0.02124 (4)
N1	0.48319 (13)	0.66074 (9)	0.94225 (8)	0.0168 (2)
N2	0.72144 (13)	0.65150 (9)	1.01988 (8)	0.0172 (2)
N3	0.07774 (13)	0.69630 (9)	0.68277 (8)	0.0178 (2)
N4	0.19471 (14)	0.67552 (10)	0.57302 (9)	0.0198 (2)
C1	0.63655 (16)	0.66612 (10)	0.94634 (10)	0.0171 (2)
H1A	0.6787	0.6786	0.9030	0.021*
C2	0.61934 (16)	0.63548 (10)	1.06701 (10)	0.0167 (2)
C3	0.64670 (17)	0.61359 (11)	1.14536 (10)	0.0193 (3)
H3A	0.7500	0.6096	1.1792	0.023*
C4	0.51353 (18)	0.59803 (11)	1.17085 (10)	0.0207 (3)
H4A	0.5262	0.5831	1.2239	0.025*
C5	0.36033 (18)	0.60365 (11)	1.12058 (11)	0.0215 (3)
H5A	0.2727	0.5921	1.1405	0.026*
C6	0.33375 (16)	0.62550 (11)	1.04280 (10)	0.0193 (3)
H6A	0.2306	0.6294	1.0088	0.023*
C7	0.46771 (16)	0.64135 (10)	1.01748 (10)	0.0166 (2)
C8	0.35503 (16)	0.67445 (11)	0.87201 (10)	0.0187 (3)
H8A	0.2604	0.6221	0.8496	0.022*
H8B	0.3889	0.6635	0.8149	0.022*
C9	0.30936 (16)	0.77994 (11)	0.91357 (10)	0.0177 (3)
C10	0.40829 (17)	0.86003 (11)	0.99982 (11)	0.0220 (3)
H10A	0.5053	0.8482	1.0332	0.026*
C11	0.36713 (19)	0.95694 (12)	1.03770 (11)	0.0252 (3)
H11A	0.4355	1.0105	1.0967	0.030*
C12	0.2263 (2)	0.97520 (12)	0.98931 (11)	0.0266 (3)
H12A	0.1980	1.0413	1.0148	0.032*
C13	0.12706 (19)	0.89630 (13)	0.90350 (11)	0.0253 (3)
H13A	0.0305	0.9089	0.8705	0.030*
C14	0.16660 (16)	0.79853 (11)	0.86476 (10)	0.0193 (3)
C15	0.04692 (16)	0.71575 (12)	0.77466 (10)	0.0204 (3)
H15A	0.0452	0.6514	0.7803	0.025*
H15B	−0.0599	0.7348	0.7715	0.025*
C16	−0.03893 (16)	0.64533 (11)	0.59265 (10)	0.0183 (3)
C17	−0.20136 (17)	0.61256 (12)	0.56824 (11)	0.0215 (3)
H17A	−0.2515	0.6215	0.6160	0.026*
C18	−0.28532 (18)	0.56616 (12)	0.46997 (11)	0.0250 (3)
H18A	−0.3966	0.5430	0.4497	0.030*
C19	−0.21027 (19)	0.55241 (12)	0.39959 (11)	0.0261 (3)
H19A	−0.2724	0.5198	0.3330	0.031*
C20	−0.04885 (19)	0.58480 (12)	0.42390 (11)	0.0246 (3)
H20A	0.0016	0.5754	0.3761	0.029*
C21	0.03504 (17)	0.63207 (11)	0.52276 (10)	0.0197 (3)
C22	0.21526 (16)	0.71327 (11)	0.66812 (10)	0.0190 (3)
H22A	0.3135	0.7472	0.7180	0.023*
C23	0.89380 (16)	0.64783 (11)	1.04495 (10)	0.0199 (3)
H23A	0.9285	0.6320	0.9872	0.024*
H23B	0.9132	0.5921	1.0632	0.024*
C24	0.99196 (17)	0.74804 (11)	1.12807 (11)	0.0217 (3)
H24A	1.1005	0.7363	1.1530	0.026*
H24B	0.9441	0.7700	1.1814	0.026*
C25	1.0042 (2)	0.83405 (12)	1.10038 (12)	0.0279 (3)
H25A	0.8967	0.8498	1.0803	0.033*
H25B	1.0449	0.8106	1.0440	0.033*
C26	1.1138 (2)	0.93188 (13)	1.18354 (13)	0.0312 (4)
H26A	1.2184	0.9146	1.2074	0.037*
H26B	1.1310	0.9804	1.1580	0.037*
C27	1.0495 (2)	0.98436 (13)	1.26812 (13)	0.0318 (4)
H27A	1.0368	0.9369	1.2954	0.038*
H27B	0.9428	0.9987	1.2436	0.038*
C28	1.1542 (3)	1.08388 (15)	1.34891 (15)	0.0474 (4)
H28A	1.1636	1.1328	1.3227	0.057*
H28B	1.2621	1.0704	1.3724	0.057*
C29	1.0880 (3)	1.13208 (15)	1.43403 (15)	0.0474 (4)
H29A	1.1598	1.1953	1.4847	0.071*
H29B	1.0790	1.0841	1.4605	0.071*
H29C	0.9827	1.1478	1.4116	0.071*
C30	0.31844 (18)	0.68129 (12)	0.52875 (11)	0.0237 (3)
H30A	0.3231	0.6112	0.4817	0.028*	0.474 (5)
H30B	0.4229	0.7092	0.5801	0.028*	0.474 (5)
H30C	0.3035	0.6192	0.4701	0.028*	0.526 (5)
H30D	0.4214	0.6897	0.5729	0.028*	0.526 (5)
C31	0.2912 (8)	0.7454 (5)	0.4784 (4)	0.0235 (11)	0.474 (5)
H31A	0.2774	0.8131	0.5252	0.028*	0.474 (5)
H31D	0.1887	0.7142	0.4256	0.028*	0.474 (5)
C32	0.4121 (14)	0.7637 (9)	0.4352 (8)	0.0239 (12)	0.474 (5)
H32A	0.3838	0.7084	0.3677	0.029*	0.474 (5)
H32D	0.5159	0.7554	0.4712	0.029*	0.474 (5)
C33	0.4379 (5)	0.8674 (3)	0.4321 (3)	0.0283 (9)	0.474 (5)
H33A	0.3348	0.8910	0.4194	0.034*	0.474 (5)
H33B	0.5095	0.9198	0.4956	0.034*	0.474 (5)
C34	0.5109 (7)	0.8542 (6)	0.3522 (5)	0.0284 (13)	0.474 (5)
H34A	0.6021	0.8179	0.3584	0.034*	0.474 (5)
H34B	0.4308	0.8102	0.2884	0.034*	0.474 (5)
C35	0.5674 (5)	0.9528 (3)	0.3533 (3)	0.0302 (9)	0.474 (5)
H35A	0.4821	0.9949	0.3581	0.036*	0.474 (5)
H35B	0.6609	0.9917	0.4114	0.036*	0.474 (5)
C36	0.6121 (7)	0.9350 (6)	0.2638 (4)	0.0435 (14)	0.474 (5)
H36A	0.6544	1.0007	0.2699	0.065*	0.474 (5)
H36B	0.5177	0.9018	0.2064	0.065*	0.474 (5)
H36C	0.6932	0.8909	0.2571	0.065*	0.474 (5)
C31X	0.3150 (8)	0.7765 (4)	0.5075 (4)	0.0293 (11)	0.526 (5)
H31B	0.2075	0.7748	0.4674	0.035*	0.526 (5)
H31C	0.3463	0.8414	0.5687	0.035*	0.526 (5)
C32X	0.4359 (12)	0.7661 (8)	0.4522 (7)	0.0239 (12)	0.526 (5)
H32B	0.4350	0.6924	0.4124	0.029*	0.526 (5)
H32C	0.5435	0.7961	0.5000	0.029*	0.526 (5)
C33X	0.4057 (4)	0.8177 (3)	0.3857 (3)	0.0265 (8)	0.526 (5)
H33C	0.3278	0.7700	0.3223	0.032*	0.526 (5)
H33D	0.3582	0.8792	0.4150	0.032*	0.526 (5)
C34X	0.5560 (6)	0.8489 (5)	0.3687 (5)	0.0227 (10)	0.526 (5)
H34C	0.6078	0.7883	0.3439	0.027*	0.526 (5)
H34D	0.6308	0.9005	0.4314	0.027*	0.526 (5)
C35X	0.5249 (4)	0.8934 (3)	0.2968 (3)	0.0292 (8)	0.526 (5)
H35C	0.4514	0.8415	0.2337	0.035*	0.526 (5)
H35D	0.4720	0.9535	0.3210	0.035*	0.526 (5)
C36X	0.6762 (6)	0.9258 (4)	0.2811 (4)	0.0358 (10)	0.526 (5)
H36D	0.6505	0.9590	0.2391	0.054*	0.526 (5)
H36E	0.7231	0.8653	0.2503	0.054*	0.526 (5)
H36F	0.7524	0.9738	0.3439	0.054*	0.526 (5)
O1W	0.39216 (15)	0.47948 (11)	0.29323 (9)	0.0324 (3)
H1W1	0.380 (3)	0.4177 (19)	0.2809 (17)	0.050 (7)*
H2W1	0.307 (3)	0.4896 (18)	0.2719 (17)	0.048 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.01641 (7)	0.02614 (8)	0.02309 (7)	0.00403 (5)	0.00799 (5)	0.01061 (6)
Br2	0.01825 (7)	0.02841 (8)	0.02049 (7)	0.00428 (5)	0.00856 (5)	0.01277 (6)
N1	0.0142 (5)	0.0200 (5)	0.0152 (5)	0.0023 (4)	0.0050 (4)	0.0069 (4)
N2	0.0143 (5)	0.0208 (6)	0.0172 (5)	0.0032 (4)	0.0067 (4)	0.0081 (5)
N3	0.0144 (5)	0.0243 (6)	0.0144 (5)	0.0029 (4)	0.0046 (4)	0.0087 (5)
N4	0.0181 (5)	0.0254 (6)	0.0185 (5)	0.0043 (5)	0.0083 (4)	0.0108 (5)
C1	0.0166 (6)	0.0182 (6)	0.0158 (6)	0.0028 (5)	0.0064 (5)	0.0064 (5)
C2	0.0159 (6)	0.0175 (6)	0.0166 (6)	0.0039 (5)	0.0077 (5)	0.0063 (5)
C3	0.0211 (6)	0.0203 (6)	0.0169 (6)	0.0055 (5)	0.0074 (5)	0.0078 (5)
C4	0.0262 (7)	0.0201 (6)	0.0186 (6)	0.0053 (5)	0.0112 (6)	0.0089 (5)
C5	0.0215 (7)	0.0210 (7)	0.0218 (7)	0.0023 (5)	0.0119 (6)	0.0068 (6)
C6	0.0157 (6)	0.0205 (6)	0.0202 (6)	0.0024 (5)	0.0079 (5)	0.0067 (5)
C7	0.0163 (6)	0.0171 (6)	0.0152 (6)	0.0026 (5)	0.0059 (5)	0.0060 (5)
C8	0.0159 (6)	0.0211 (6)	0.0155 (6)	0.0017 (5)	0.0025 (5)	0.0066 (5)
C9	0.0164 (6)	0.0214 (6)	0.0161 (6)	0.0029 (5)	0.0061 (5)	0.0087 (5)
C10	0.0194 (6)	0.0242 (7)	0.0199 (7)	0.0030 (5)	0.0041 (5)	0.0090 (6)
C11	0.0299 (8)	0.0224 (7)	0.0204 (7)	0.0030 (6)	0.0084 (6)	0.0071 (6)
C12	0.0350 (8)	0.0250 (7)	0.0243 (7)	0.0127 (6)	0.0144 (7)	0.0118 (6)
C13	0.0251 (7)	0.0347 (8)	0.0228 (7)	0.0131 (6)	0.0116 (6)	0.0163 (6)
C14	0.0169 (6)	0.0276 (7)	0.0159 (6)	0.0048 (5)	0.0071 (5)	0.0110 (6)
C15	0.0145 (6)	0.0327 (8)	0.0153 (6)	0.0032 (5)	0.0050 (5)	0.0119 (6)
C16	0.0172 (6)	0.0221 (6)	0.0152 (6)	0.0038 (5)	0.0042 (5)	0.0088 (5)
C17	0.0172 (6)	0.0272 (7)	0.0202 (7)	0.0042 (5)	0.0056 (5)	0.0111 (6)
C18	0.0193 (7)	0.0274 (7)	0.0235 (7)	0.0030 (6)	0.0022 (6)	0.0100 (6)
C19	0.0259 (7)	0.0301 (8)	0.0162 (6)	0.0045 (6)	0.0017 (6)	0.0080 (6)
C20	0.0267 (7)	0.0294 (8)	0.0173 (6)	0.0063 (6)	0.0078 (6)	0.0097 (6)
C21	0.0188 (6)	0.0229 (7)	0.0181 (6)	0.0044 (5)	0.0062 (5)	0.0096 (5)
C22	0.0162 (6)	0.0241 (7)	0.0180 (6)	0.0038 (5)	0.0055 (5)	0.0107 (5)
C23	0.0144 (6)	0.0255 (7)	0.0204 (6)	0.0062 (5)	0.0073 (5)	0.0097 (6)
C24	0.0170 (6)	0.0262 (7)	0.0201 (7)	0.0032 (5)	0.0053 (5)	0.0093 (6)
C25	0.0299 (8)	0.0288 (8)	0.0273 (8)	0.0018 (6)	0.0098 (6)	0.0146 (7)
C26	0.0244 (7)	0.0263 (8)	0.0414 (9)	0.0019 (6)	0.0123 (7)	0.0133 (7)
C27	0.0341 (9)	0.0273 (8)	0.0314 (8)	0.0028 (7)	0.0096 (7)	0.0117 (7)
C28	0.0601 (10)	0.0289 (7)	0.0402 (8)	0.0077 (6)	0.0086 (7)	0.0084 (6)
C29	0.0601 (10)	0.0289 (7)	0.0402 (8)	0.0077 (6)	0.0086 (7)	0.0084 (6)
C30	0.0207 (7)	0.0316 (8)	0.0224 (7)	0.0046 (6)	0.0120 (6)	0.0125 (6)
C31	0.021 (2)	0.025 (3)	0.026 (3)	0.003 (2)	0.010 (2)	0.011 (2)
C32	0.026 (3)	0.0297 (9)	0.012 (3)	−0.0043 (14)	0.004 (2)	0.0073 (17)
C33	0.037 (2)	0.0225 (19)	0.030 (2)	0.0061 (16)	0.0182 (17)	0.0121 (17)
C34	0.032 (3)	0.027 (2)	0.023 (3)	0.005 (2)	0.009 (2)	0.0084 (18)
C35	0.0307 (18)	0.033 (2)	0.030 (2)	0.0012 (15)	0.0108 (15)	0.0166 (18)
C36	0.038 (3)	0.062 (3)	0.042 (3)	0.003 (3)	0.017 (3)	0.030 (2)
C31X	0.031 (3)	0.030 (3)	0.037 (3)	0.008 (2)	0.017 (3)	0.021 (2)
C32X	0.026 (3)	0.0297 (9)	0.012 (3)	−0.0043 (14)	0.004 (2)	0.0073 (17)
C33X	0.0217 (14)	0.0299 (19)	0.0300 (18)	0.0033 (13)	0.0101 (13)	0.0146 (16)
C34X	0.023 (2)	0.0247 (18)	0.024 (2)	0.0026 (18)	0.0094 (19)	0.0138 (16)
C35X	0.0295 (16)	0.0322 (19)	0.0263 (17)	0.0002 (13)	0.0099 (13)	0.0135 (16)
C36X	0.035 (2)	0.042 (2)	0.039 (2)	0.002 (2)	0.017 (2)	0.0231 (19)
O1W	0.0238 (6)	0.0322 (7)	0.0347 (7)	−0.0010 (5)	−0.0019 (5)	0.0163 (6)

Geometric parameters (Å, º) top

N1—C1	1.3391 (17)	C25—H25B	0.9900
N1—C7	1.3961 (17)	C26—C27	1.517 (2)
N1—C8	1.4618 (18)	C26—H26A	0.9900
N2—C1	1.3304 (18)	C26—H26B	0.9900
N2—C2	1.3965 (17)	C27—C28	1.520 (3)
N2—C23	1.4799 (18)	C27—H27A	0.9900
N3—C22	1.3348 (17)	C27—H27B	0.9900
N3—C16	1.3928 (17)	C28—C29	1.527 (3)
N3—C15	1.4808 (18)	C28—H28A	0.9900
N4—C22	1.3377 (18)	C28—H28B	0.9900
N4—C21	1.3940 (18)	C29—H29A	0.9800
N4—C30	1.4740 (18)	C29—H29B	0.9800
C1—H1A	0.9500	C29—H29C	0.9800
C2—C7	1.3940 (19)	C30—C31	1.475 (8)
C2—C3	1.3949 (19)	C30—C31X	1.580 (7)
C3—C4	1.389 (2)	C30—H30A	0.9900
C3—H3A	0.9500	C30—H30B	0.9900
C4—C5	1.408 (2)	C30—H30C	0.9600
C4—H4A	0.9500	C30—H30D	0.9600
C5—C6	1.386 (2)	C31—C32	1.496 (9)
C5—H5A	0.9500	C31—H31A	0.9900
C6—C7	1.3947 (19)	C31—H31D	0.9900
C6—H6A	0.9500	C32—C33	1.560 (10)
C8—C9	1.519 (2)	C32—H32A	0.9900
C8—H8A	0.9900	C32—H32D	0.9900
C8—H8B	0.9900	C33—C34	1.529 (7)
C9—C10	1.3955 (19)	C33—H33A	0.9900
C9—C14	1.404 (2)	C33—H33B	0.9900
C10—C11	1.392 (2)	C34—C35	1.511 (7)
C10—H10A	0.9500	C34—H34A	0.9900
C11—C12	1.386 (2)	C34—H34B	0.9900
C11—H11A	0.9500	C35—C36	1.508 (6)
C12—C13	1.386 (2)	C35—H35A	0.9900
C12—H12A	0.9500	C35—H35B	0.9900
C13—C14	1.398 (2)	C36—H36A	0.9800
C13—H13A	0.9500	C36—H36B	0.9800
C14—C15	1.507 (2)	C36—H36C	0.9800
C15—H15A	0.9900	C31X—C32X	1.534 (9)
C15—H15B	0.9900	C31X—H31B	0.9900
C16—C21	1.392 (2)	C31X—H31C	0.9900
C16—C17	1.3936 (19)	C32X—C33X	1.536 (8)
C17—C18	1.387 (2)	C32X—H32B	0.9900
C17—H17A	0.9500	C32X—H32C	0.9900
C18—C19	1.404 (2)	C33X—C34X	1.522 (6)
C18—H18A	0.9500	C33X—H33C	0.9900
C19—C20	1.384 (2)	C33X—H33D	0.9900
C19—H19A	0.9500	C34X—C35X	1.529 (6)
C20—C21	1.394 (2)	C34X—H34C	0.9900
C20—H20A	0.9500	C34X—H34D	0.9900
C22—H22A	0.9500	C35X—C36X	1.524 (5)
C23—C24	1.518 (2)	C35X—H35C	0.9900
C23—H23A	0.9900	C35X—H35D	0.9900
C23—H23B	0.9900	C36X—H36D	0.9800
C24—C25	1.522 (2)	C36X—H36E	0.9800
C24—H24A	0.9900	C36X—H36F	0.9800
C24—H24B	0.9900	O1W—H1W1	0.84 (2)
C25—C26	1.533 (2)	O1W—H2W1	0.79 (3)
C25—H25A	0.9900

C1—N1—C7	108.14 (11)	C27—C26—H26B	108.8
C1—N1—C8	125.77 (12)	C25—C26—H26B	108.8
C7—N1—C8	126.08 (11)	H26A—C26—H26B	107.7
C1—N2—C2	108.59 (11)	C26—C27—C28	114.01 (16)
C1—N2—C23	125.85 (12)	C26—C27—H27A	108.8
C2—N2—C23	125.50 (12)	C28—C27—H27A	108.8
C22—N3—C16	108.14 (11)	C26—C27—H27B	108.8
C22—N3—C15	128.98 (12)	C28—C27—H27B	108.8
C16—N3—C15	122.61 (11)	H27A—C27—H27B	107.6
C22—N4—C21	108.35 (12)	C27—C28—C29	112.23 (19)
C22—N4—C30	125.98 (12)	C27—C28—H28A	109.2
C21—N4—C30	125.65 (12)	C29—C28—H28A	109.2
N2—C1—N1	110.19 (12)	C27—C28—H28B	109.2
N2—C1—H1A	124.9	C29—C28—H28B	109.2
N1—C1—H1A	124.9	H28A—C28—H28B	107.9
C7—C2—C3	122.01 (13)	C28—C29—H29A	109.5
C7—C2—N2	106.38 (12)	C28—C29—H29B	109.5
C3—C2—N2	131.57 (13)	H29A—C29—H29B	109.5
C4—C3—C2	115.83 (13)	C28—C29—H29C	109.5
C4—C3—H3A	122.1	H29A—C29—H29C	109.5
C2—C3—H3A	122.1	H29B—C29—H29C	109.5
C3—C4—C5	122.12 (13)	N4—C30—C31	113.6 (3)
C3—C4—H4A	118.9	N4—C30—C31X	110.5 (3)
C5—C4—H4A	118.9	N4—C30—H30A	108.9
C6—C5—C4	121.84 (13)	C31—C30—H30A	108.9
C6—C5—H5A	119.1	N4—C30—H30B	108.9
C4—C5—H5A	119.1	C31—C30—H30B	108.9
C5—C6—C7	115.94 (13)	H30A—C30—H30B	107.7
C5—C6—H6A	122.0	N4—C30—H30C	110.1
C7—C6—H6A	122.0	C31—C30—H30C	93.8
C2—C7—C6	122.25 (13)	C31X—C30—H30C	110.5
C2—C7—N1	106.71 (11)	H30B—C30—H30C	121.1
C6—C7—N1	130.99 (13)	N4—C30—H30D	109.5
N1—C8—C9	112.83 (11)	C31—C30—H30D	120.1
N1—C8—H8A	109.0	C31X—C30—H30D	107.8
C9—C8—H8A	109.0	H30A—C30—H30D	93.7
N1—C8—H8B	109.0	H30C—C30—H30D	108.3
C9—C8—H8B	109.0	C30—C31—C32	119.6 (6)
H8A—C8—H8B	107.8	C30—C31—H31A	107.4
C10—C9—C14	118.88 (13)	C32—C31—H31A	107.4
C10—C9—C8	120.99 (13)	C30—C31—H31D	107.4
C14—C9—C8	120.13 (12)	C32—C31—H31D	107.4
C11—C10—C9	121.08 (14)	H31A—C31—H31D	106.9
C11—C10—H10A	119.5	C31—C32—C33	119.7 (9)
C9—C10—H10A	119.5	C31—C32—H32A	107.4
C12—C11—C10	119.96 (14)	C33—C32—H32A	107.4
C12—C11—H11A	120.0	C31—C32—H32D	107.4
C10—C11—H11A	120.0	C33—C32—H32D	107.4
C11—C12—C13	119.53 (15)	H32A—C32—H32D	106.9
C11—C12—H12A	120.2	C34—C33—C32	110.0 (6)
C13—C12—H12A	120.2	C34—C33—H33A	109.7
C12—C13—C14	121.15 (14)	C32—C33—H33A	109.7
C12—C13—H13A	119.4	C34—C33—H33B	109.7
C14—C13—H13A	119.4	C32—C33—H33B	109.7
C13—C14—C9	119.41 (13)	H33A—C33—H33B	108.2
C13—C14—C15	117.53 (13)	C35—C34—C33	114.8 (5)
C9—C14—C15	122.95 (13)	C35—C34—H34A	108.6
N3—C15—C14	114.66 (11)	C33—C34—H34A	108.6
N3—C15—H15A	108.6	C35—C34—H34B	108.6
C14—C15—H15A	108.6	C33—C34—H34B	108.6
N3—C15—H15B	108.6	H34A—C34—H34B	107.5
C14—C15—H15B	108.6	C36—C35—C34	112.6 (5)
H15A—C15—H15B	107.6	C36—C35—H35A	109.1
C21—C16—N3	106.94 (12)	C34—C35—H35A	109.1
C21—C16—C17	122.16 (13)	C36—C35—H35B	109.1
N3—C16—C17	130.88 (13)	C34—C35—H35B	109.1
C18—C17—C16	115.95 (14)	H35A—C35—H35B	107.8
C18—C17—H17A	122.0	C32X—C31X—C30	104.7 (5)
C16—C17—H17A	122.0	C32X—C31X—H31B	110.8
C17—C18—C19	121.77 (14)	C30—C31X—H31B	110.8
C17—C18—H18A	119.1	C32X—C31X—H31C	110.8
C19—C18—H18A	119.1	C30—C31X—H31C	110.8
C20—C19—C18	122.23 (14)	H31B—C31X—H31C	108.9
C20—C19—H19A	118.9	C31X—C32X—C33X	114.6 (7)
C18—C19—H19A	118.9	C31X—C32X—H32B	108.6
C19—C20—C21	115.87 (14)	C33X—C32X—H32B	108.6
C19—C20—H20A	122.1	C31X—C32X—H32C	108.6
C21—C20—H20A	122.1	C33X—C32X—H32C	108.6
C16—C21—C20	122.01 (13)	H32B—C32X—H32C	107.6
C16—C21—N4	106.38 (12)	C34X—C33X—C32X	113.1 (5)
C20—C21—N4	131.60 (14)	C34X—C33X—H33C	109.0
N3—C22—N4	110.19 (12)	C32X—C33X—H33C	109.0
N3—C22—H22A	124.9	C34X—C33X—H33D	109.0
N4—C22—H22A	124.9	C32X—C33X—H33D	109.0
N2—C23—C24	112.21 (12)	H33C—C33X—H33D	107.8
N2—C23—H23A	109.2	C33X—C34X—C35X	113.3 (4)
C24—C23—H23A	109.2	C33X—C34X—H34C	108.9
N2—C23—H23B	109.2	C35X—C34X—H34C	108.9
C24—C23—H23B	109.2	C33X—C34X—H34D	108.9
H23A—C23—H23B	107.9	C35X—C34X—H34D	108.9
C23—C24—C25	113.95 (13)	H34C—C34X—H34D	107.7
C23—C24—H24A	108.8	C36X—C35X—C34X	113.0 (4)
C25—C24—H24A	108.8	C36X—C35X—H35C	109.0
C23—C24—H24B	108.8	C34X—C35X—H35C	109.0
C25—C24—H24B	108.8	C36X—C35X—H35D	109.0
H24A—C24—H24B	107.7	C34X—C35X—H35D	109.0
C24—C25—C26	112.82 (14)	H35C—C35X—H35D	107.8
C24—C25—H25A	109.0	C35X—C36X—H36D	109.5
C26—C25—H25A	109.0	C35X—C36X—H36E	109.5
C24—C25—H25B	109.0	H36D—C36X—H36E	109.5
C26—C25—H25B	109.0	C35X—C36X—H36F	109.5
H25A—C25—H25B	107.8	H36D—C36X—H36F	109.5
C27—C26—C25	113.75 (14)	H36E—C36X—H36F	109.5
C27—C26—H26A	108.8	H1W1—O1W—H2W1	106 (2)
C25—C26—H26A	108.8

C2—N2—C1—N1	0.07 (16)	C22—N3—C16—C17	−178.32 (16)
C23—N2—C1—N1	177.39 (12)	C15—N3—C16—C17	7.2 (2)
C7—N1—C1—N2	−0.09 (16)	C21—C16—C17—C18	−0.2 (2)
C8—N1—C1—N2	179.03 (12)	N3—C16—C17—C18	178.08 (15)
C1—N2—C2—C7	−0.02 (15)	C16—C17—C18—C19	0.5 (2)
C23—N2—C2—C7	−177.35 (12)	C17—C18—C19—C20	−0.4 (3)
C1—N2—C2—C3	177.66 (15)	C18—C19—C20—C21	0.0 (2)
C23—N2—C2—C3	0.3 (2)	N3—C16—C21—C20	−178.90 (14)
C7—C2—C3—C4	0.0 (2)	C17—C16—C21—C20	−0.3 (2)
N2—C2—C3—C4	−177.37 (14)	N3—C16—C21—N4	0.06 (16)
C2—C3—C4—C5	0.2 (2)	C17—C16—C21—N4	178.71 (14)
C3—C4—C5—C6	−0.3 (2)	C19—C20—C21—C16	0.4 (2)
C4—C5—C6—C7	0.1 (2)	C19—C20—C21—N4	−178.30 (15)
C3—C2—C7—C6	−0.2 (2)	C22—N4—C21—C16	−0.27 (16)
N2—C2—C7—C6	177.79 (13)	C30—N4—C21—C16	−178.69 (13)
C3—C2—C7—N1	−177.98 (12)	C22—N4—C21—C20	178.56 (16)
N2—C2—C7—N1	−0.03 (15)	C30—N4—C21—C20	0.1 (3)
C5—C6—C7—C2	0.1 (2)	C16—N3—C22—N4	−0.34 (17)
C5—C6—C7—N1	177.34 (14)	C15—N3—C22—N4	173.71 (14)
C1—N1—C7—C2	0.07 (15)	C21—N4—C22—N3	0.38 (17)
C8—N1—C7—C2	−179.04 (12)	C30—N4—C22—N3	178.80 (13)
C1—N1—C7—C6	−177.48 (14)	C1—N2—C23—C24	100.16 (16)
C8—N1—C7—C6	3.4 (2)	C2—N2—C23—C24	−82.96 (17)
C1—N1—C8—C9	−101.05 (16)	N2—C23—C24—C25	−73.02 (16)
C7—N1—C8—C9	77.90 (16)	C23—C24—C25—C26	−175.79 (13)
N1—C8—C9—C10	15.32 (18)	C24—C25—C26—C27	−67.89 (19)
N1—C8—C9—C14	−165.31 (12)	C25—C26—C27—C28	−177.48 (16)
C14—C9—C10—C11	0.2 (2)	C26—C27—C28—C29	−177.98 (17)
C8—C9—C10—C11	179.59 (13)	C22—N4—C30—C31	−113.8 (3)
C9—C10—C11—C12	−0.3 (2)	C21—N4—C30—C31	64.4 (3)
C10—C11—C12—C13	0.3 (2)	C22—N4—C30—C31X	−95.1 (3)
C11—C12—C13—C14	−0.1 (2)	C21—N4—C30—C31X	83.1 (3)
C12—C13—C14—C9	−0.1 (2)	N4—C30—C31—C32	176.3 (6)
C12—C13—C14—C15	176.19 (14)	C31X—C30—C31—C32	92.5 (18)
C10—C9—C14—C13	0.0 (2)	C30—C31—C32—C33	−147.7 (6)
C8—C9—C14—C13	−179.39 (13)	C31—C32—C33—C34	−157.1 (7)
C10—C9—C14—C15	−176.05 (13)	C32—C33—C34—C35	−170.0 (5)
C8—C9—C14—C15	4.6 (2)	C33—C34—C35—C36	−170.2 (4)
C22—N3—C15—C14	25.2 (2)	N4—C30—C31X—C32X	−174.1 (4)
C16—N3—C15—C14	−161.53 (13)	C31—C30—C31X—C32X	−70.8 (16)
C13—C14—C15—N3	97.87 (16)	C30—C31X—C32X—C33X	154.5 (6)
C9—C14—C15—N3	−86.02 (17)	C31X—C32X—C33X—C34X	154.0 (6)
C22—N3—C16—C21	0.16 (16)	C32X—C33X—C34X—C35X	175.9 (6)
C15—N3—C16—C21	−174.34 (13)	C33X—C34X—C35X—C36X	179.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···Br1	0.84 (3)	2.50 (3)	3.3271 (17)	169 (2)
O1W—H2W1···Br2	0.79 (3)	2.54 (3)	3.3280 (14)	177 (3)
C1—H1A···Br1ⁱ	0.95	2.80	3.6093 (15)	144
C3—H3A···Br2ⁱⁱ	0.95	2.92	3.7866 (16)	153
C5—H5A···Br2ⁱⁱⁱ	0.95	2.89	3.8162 (17)	167
C8—H8A···Br2^iv	0.99	2.93	3.9117 (16)	172
C15—H15A···Br2^iv	0.99	2.72	3.6809 (19)	165
C15—H15B···Br1^iv	0.99	2.80	3.7842 (15)	170
C18—H18A···O1W^v	0.95	2.46	3.187 (2)	133
C20—H20A···Br2	0.95	2.76	3.6602 (16)	158
C22—H22A···Br1ⁱ	0.95	2.70	3.5577 (15)	150
C23—H23A···Br2ⁱ	0.99	2.89	3.7836 (14)	151
C23—H23B···Br2ⁱⁱ	0.99	2.81	3.7285 (17)	154

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z+1; (iii) x, y, z+1; (iv) −x, −y+1, −z+1; (v) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₃₆H₄₈N₄²⁺·2Br⁻·H₂O
M_r	714.62
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.8494 (1), 14.7170 (3), 16.0838 (2)
α, β, γ (°)	115.705 (1), 105.380 (1), 91.946 (1)
V (Å³)	1792.83 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.29
Crystal size (mm)	0.39 × 0.18 × 0.16

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.469, 0.715
No. of measured, independent and observed [I > 2σ(I)] reflections	50860, 12945, 10091
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.077, 1.02
No. of reflections	12945
No. of parameters	442
No. of restraints	9
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.84, −0.75

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···Br1	0.84 (3)	2.50 (3)	3.3271 (17)	169 (2)
O1W—H2W1···Br2	0.79 (3)	2.54 (3)	3.3280 (14)	177 (3)
C1—H1A···Br1ⁱ	0.95	2.80	3.6093 (15)	144
C3—H3A···Br2ⁱⁱ	0.95	2.92	3.7866 (16)	153
C5—H5A···Br2ⁱⁱⁱ	0.95	2.89	3.8162 (17)	167
C8—H8A···Br2^iv	0.99	2.93	3.9117 (16)	172
C15—H15A···Br2^iv	0.99	2.72	3.6809 (19)	165
C15—H15B···Br1^iv	0.99	2.80	3.7842 (15)	170
C18—H18A···O1W^v	0.95	2.46	3.187 (2)	133
C20—H20A···Br2	0.95	2.76	3.6602 (16)	158
C22—H22A···Br1ⁱ	0.95	2.70	3.5577 (15)	150
C23—H23A···Br2ⁱ	0.99	2.89	3.7836 (14)	151
C23—H23B···Br2ⁱⁱ	0.99	2.81	3.7285 (17)	154

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z+1; (iii) x, y, z+1; (iv) −x, −y+1, −z+1; (v) x−1, y, z.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

RAH thanks Universiti Sains Malaysia (USM) for the FRGS fund (203/PKIMIA/671115), short term grant (304/PKIMIA639001), and RU grants (1001/PKIMIA/811157) and (1001/PKIMIA/823082). MAI is grateful to (IPS) USM for financial support [fellowship: USM.IPS/JWT/1/19 (JLD 6)]. HKF and MH thank the Malaysian Government and UUSM for the Research University Grant No. 1001/PFIZIK/811160. MH thanks USM for a post-doctoral research fellowship.

References

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Volume 67| Part 7| July 2011| Pages o1814-o1815

doi:10.1107/S1600536811023476

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3,3′-[1,2-Phenyl­enebis(methyl­ene)]bis­­(1-heptyl­benzimidazolium) dibromide monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

3,3′-[1,2-Phenylenebis(methylene)]bis(1-heptylbenzimidazolium) dibromide monohydrate