1,3-Bis[4-(meth-oxy-carbon-yl)benz-yl]benzimidazolium bromide monohydrate.

In the title compound, C(25)H(23)N(2)O(4) (+)·Br(-)·H(2)O, the dihedral angles between the benzimidazole ring system and the two benzene rings are 87.77 (11) and 63.05 (11)°; the dihedral angle between the two benzene rings is 66.25 (13)°. The crystal structure exhibits C-H⋯O and O-H⋯Br inter-actions; it is also stabilized by π-π stacking inter-actions, with a face-to-face separation of 3.456 Å between parallel benzimidazole ring systems.

Related literature

For general background to and the therapeutic properties of benzimidazole derivatives, see: Herrmann (2002 ▶); Herrmann et al. (1995 ▶, 1998 ▶); Navarro et al. (2006 ▶). For related structures, see: Akkurt et al. (2005 ▶); Pınar et al. (2006 ▶); Arslan et al. (2009 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C25H23N2O4 +·Br−·H2O

M = 513.38

Monoclinic,

a = 13.604 (2) Å

b = 9.3537 (16) Å

c = 18.962 (3) Å

β = 107.006 (3)°

V = 2307.4 (7) Å3

Z = 4

Mo Kα radiation

μ = 1.82 mm−1

T = 110 K

0.39 × 0.36 × 0.35 mm

Data collection

Bruker SMART CCD 1K area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.537, T max = 0.568

13524 measured reflections

5002 independent reflections

3422 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.096

S = 1.05

5002 reflections

300 parameters

H-atom parameters constrained

Δρmax = 0.78 e Å−3

Δρmin = −0.35 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT-Plus (Bruker, 1999 ▶); data reduction: SAINT-Plus; 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810041929/wn2412sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041929/wn2412Isup2.hkl

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

C25H23N2O4+·Br−·H2O	F(000) = 1056
Mr = 513.38	Dx = 1.478 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3740 reflections
a = 13.604 (2) Å	θ = 2.3–26.8°
b = 9.3537 (16) Å	µ = 1.82 mm−1
c = 18.962 (3) Å	T = 110 K
β = 107.006 (3)°	Block, colorless
V = 2307.4 (7) Å3	0.39 × 0.36 × 0.35 mm
Z = 4

Bruker SMART CCD 1K area-detector diffractometer	5002 independent reflections
Radiation source: fine-focus sealed tube	3422 reflections with I > 2σ(I)
graphite	Rint = 0.046
φ and ω scans	θmax = 27.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→15
Tmin = 0.537, Tmax = 0.568	k = −11→11
13524 measured reflections	l = −18→24

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0417P)2 + 0.4447P] where P = (Fo2 + 2Fc2)/3
5002 reflections	(Δ/σ)max < 0.001
300 parameters	Δρmax = 0.78 e Å−3
0 restraints	Δρmin = −0.35 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
Br1	0.51077 (2)	0.40648 (3)	0.834559 (16)	0.02439 (10)
C1	0.6347 (2)	0.3275 (3)	0.63706 (15)	0.0175 (6)
H1	0.6346	0.2667	0.6772	0.021*
C2	0.6389 (2)	0.5212 (3)	0.57082 (15)	0.0145 (6)
C3	0.63019 (19)	0.4021 (3)	0.52566 (14)	0.0137 (6)
C4	0.6237 (2)	0.4155 (3)	0.45119 (15)	0.0178 (6)
H4	0.6179	0.3347	0.4198	0.021*
C5	0.6263 (2)	0.5528 (3)	0.42594 (16)	0.0233 (7)
H5	0.6223	0.5668	0.3756	0.028*
C6	0.6346 (2)	0.6733 (3)	0.47144 (16)	0.0214 (7)
H6	0.6357	0.7658	0.4511	0.026*
C7	0.6410 (2)	0.6601 (3)	0.54498 (16)	0.0201 (7)
H7	0.6466	0.7410	0.5762	0.024*
C8	0.6423 (2)	0.5565 (3)	0.70503 (15)	0.0200 (7)
H8A	0.6190	0.4961	0.7399	0.024*
H8B	0.5916	0.6346	0.6886	0.024*
C9	0.7443 (2)	0.6214 (3)	0.74563 (15)	0.0175 (6)
C10	0.8378 (2)	0.5707 (3)	0.74080 (15)	0.0198 (7)
H10	0.8398	0.4923	0.7094	0.024*
C11	0.9281 (2)	0.6342 (3)	0.78168 (16)	0.0209 (7)
H11	0.9919	0.5990	0.7780	0.025*
C12	0.9273 (2)	0.7487 (3)	0.82806 (15)	0.0172 (6)
C13	0.8336 (2)	0.7982 (3)	0.83393 (16)	0.0229 (7)
H13	0.8317	0.8746	0.8665	0.027*
C14	0.7432 (2)	0.7356 (3)	0.79225 (16)	0.0237 (7)
H14	0.6793	0.7713	0.7955	0.028*
C15	1.0268 (2)	0.8163 (3)	0.86905 (16)	0.0202 (7)
C16	1.1068 (2)	0.9863 (4)	0.96014 (18)	0.0311 (8)
H16A	1.1500	0.9130	0.9913	0.047*
H16B	1.0889	1.0592	0.9914	0.047*
H16C	1.1443	1.0309	0.9290	0.047*
C17	0.6111 (2)	0.1329 (3)	0.54368 (16)	0.0180 (6)
H17A	0.5744	0.1315	0.4902	0.022*
H17B	0.5669	0.0846	0.5696	0.022*
C18	0.7096 (2)	0.0511 (3)	0.55708 (16)	0.0183 (6)
C19	0.7559 (2)	−0.0094 (3)	0.62603 (16)	0.0198 (7)
H19	0.7242	0.0011	0.6643	0.024*
C20	0.8467 (2)	−0.0841 (3)	0.63950 (16)	0.0203 (6)
H20	0.8774	−0.1250	0.6867	0.024*
C21	0.8938 (2)	−0.0994 (3)	0.58324 (17)	0.0221 (7)
C22	0.8476 (2)	−0.0409 (3)	0.51461 (17)	0.0246 (7)
H22	0.8788	−0.0526	0.4762	0.029*
C23	0.7567 (2)	0.0343 (3)	0.50129 (17)	0.0238 (7)
H23	0.7260	0.0747	0.4540	0.029*
C24	0.9937 (2)	−0.1754 (3)	0.5955 (2)	0.0281 (8)
C25	1.1340 (2)	−0.2807 (4)	0.6830 (2)	0.0410 (9)
H25A	1.1294	−0.3672	0.6531	0.061*
H25B	1.1572	−0.3061	0.7354	0.061*
H25C	1.1832	−0.2141	0.6720	0.061*
N1	0.64248 (17)	0.4697 (2)	0.64073 (12)	0.0159 (5)
N2	0.62711 (17)	0.2832 (2)	0.56895 (12)	0.0150 (5)
O1	1.10918 (15)	0.7850 (2)	0.86183 (11)	0.0258 (5)
O2	1.01338 (14)	0.9206 (2)	0.91378 (11)	0.0246 (5)
O3	1.03392 (18)	−0.1982 (3)	0.54791 (14)	0.0406 (6)
O4	1.03454 (16)	−0.2138 (2)	0.66612 (12)	0.0312 (5)
O1W	0.63208 (16)	0.1475 (2)	0.77270 (11)	0.0273 (5)
H1A	0.5960	0.2114	0.7851	0.041*
H1B	0.5933	0.0829	0.7485	0.041*

	U11	U22	U33	U12	U13	U23
Br1	0.02588 (17)	0.02610 (17)	0.02259 (17)	0.00320 (15)	0.00927 (12)	0.00488 (14)
C1	0.0135 (15)	0.0212 (16)	0.0173 (16)	0.0022 (12)	0.0037 (12)	0.0028 (13)
C2	0.0114 (14)	0.0154 (15)	0.0157 (15)	−0.0003 (11)	0.0027 (11)	0.0001 (12)
C3	0.0089 (13)	0.0144 (13)	0.0162 (14)	−0.0020 (12)	0.0012 (10)	0.0015 (12)
C4	0.0184 (15)	0.0191 (15)	0.0160 (14)	−0.0049 (13)	0.0052 (11)	−0.0032 (13)
C5	0.0225 (16)	0.0270 (17)	0.0200 (16)	−0.0031 (13)	0.0054 (13)	0.0037 (13)
C6	0.0181 (16)	0.0179 (16)	0.0272 (17)	−0.0026 (13)	0.0054 (13)	0.0061 (13)
C7	0.0178 (16)	0.0163 (15)	0.0261 (17)	−0.0013 (12)	0.0065 (13)	−0.0001 (13)
C8	0.0220 (16)	0.0240 (16)	0.0159 (15)	0.0011 (13)	0.0087 (12)	−0.0054 (12)
C9	0.0186 (15)	0.0216 (16)	0.0140 (15)	−0.0008 (12)	0.0073 (12)	0.0011 (12)
C10	0.0236 (16)	0.0175 (15)	0.0183 (15)	0.0029 (13)	0.0062 (12)	−0.0007 (12)
C11	0.0163 (15)	0.0210 (16)	0.0259 (17)	0.0043 (12)	0.0069 (13)	0.0042 (13)
C12	0.0175 (15)	0.0193 (15)	0.0142 (14)	−0.0014 (12)	0.0040 (12)	0.0016 (12)
C13	0.0238 (17)	0.0246 (17)	0.0218 (17)	−0.0007 (13)	0.0091 (13)	−0.0083 (13)
C14	0.0150 (15)	0.0323 (18)	0.0256 (17)	0.0026 (13)	0.0084 (13)	−0.0106 (14)
C15	0.0177 (16)	0.0213 (16)	0.0213 (16)	0.0019 (13)	0.0051 (12)	0.0041 (13)
C16	0.0222 (18)	0.041 (2)	0.0300 (19)	−0.0085 (15)	0.0067 (14)	−0.0140 (16)
C17	0.0208 (16)	0.0119 (14)	0.0199 (16)	−0.0027 (12)	0.0039 (12)	−0.0001 (12)
C18	0.0184 (15)	0.0118 (14)	0.0246 (16)	−0.0042 (12)	0.0060 (12)	−0.0025 (12)
C19	0.0216 (16)	0.0175 (15)	0.0223 (16)	−0.0033 (13)	0.0097 (13)	−0.0007 (13)
C20	0.0196 (15)	0.0146 (14)	0.0248 (16)	−0.0036 (13)	0.0033 (12)	−0.0004 (13)
C21	0.0208 (15)	0.0135 (14)	0.0333 (18)	−0.0008 (13)	0.0100 (13)	−0.0006 (14)
C22	0.0268 (17)	0.0201 (16)	0.0306 (18)	−0.0003 (14)	0.0145 (14)	−0.0017 (14)
C23	0.0291 (18)	0.0193 (16)	0.0238 (17)	0.0008 (14)	0.0089 (14)	0.0044 (13)
C24	0.0225 (17)	0.0198 (17)	0.045 (2)	−0.0019 (14)	0.0142 (16)	0.0007 (15)
C25	0.0204 (18)	0.034 (2)	0.064 (3)	0.0094 (16)	0.0054 (17)	−0.0011 (19)
N1	0.0152 (13)	0.0175 (12)	0.0161 (13)	0.0005 (10)	0.0061 (10)	−0.0024 (10)
N2	0.0146 (12)	0.0133 (12)	0.0163 (13)	−0.0014 (10)	0.0029 (10)	0.0017 (10)
O1	0.0178 (12)	0.0253 (12)	0.0345 (13)	0.0012 (9)	0.0077 (9)	−0.0024 (10)
O2	0.0154 (10)	0.0332 (13)	0.0247 (11)	−0.0023 (10)	0.0050 (8)	−0.0103 (10)
O3	0.0364 (14)	0.0392 (15)	0.0547 (17)	0.0107 (12)	0.0267 (13)	0.0050 (12)
O4	0.0196 (11)	0.0291 (12)	0.0432 (15)	0.0067 (10)	0.0065 (10)	0.0029 (11)
O1W	0.0282 (12)	0.0296 (12)	0.0249 (12)	−0.0060 (10)	0.0092 (10)	−0.0058 (10)

C1—N2	1.331 (3)	C15—O1	1.205 (3)
C1—N1	1.334 (3)	C15—O2	1.340 (3)
C1—H1	0.9500	C16—O2	1.453 (3)
C2—C3	1.389 (4)	C16—H16A	0.9800
C2—C7	1.392 (4)	C16—H16B	0.9800
C2—N1	1.398 (3)	C16—H16C	0.9800
C3—N2	1.390 (3)	C17—N2	1.481 (3)
C3—C4	1.394 (4)	C17—C18	1.499 (4)
C4—C5	1.375 (4)	C17—H17A	0.9900
C4—H4	0.9500	C17—H17B	0.9900
C5—C6	1.403 (4)	C18—C19	1.394 (4)
C5—H5	0.9500	C18—C23	1.396 (4)
C6—C7	1.377 (4)	C19—C20	1.378 (4)
C6—H6	0.9500	C19—H19	0.9500
C7—H7	0.9500	C20—C21	1.403 (4)
C8—N1	1.466 (3)	C20—H20	0.9500
C8—C9	1.504 (4)	C21—C22	1.382 (4)
C8—H8A	0.9900	C21—C24	1.490 (4)
C8—H8B	0.9900	C22—C23	1.381 (4)
C9—C10	1.385 (4)	C22—H22	0.9500
C9—C14	1.390 (4)	C23—H23	0.9500
C10—C11	1.381 (4)	C24—O3	1.204 (4)
C10—H10	0.9500	C24—O4	1.340 (4)
C11—C12	1.388 (4)	C25—O4	1.439 (4)
C11—H11	0.9500	C25—H25A	0.9800
C12—C13	1.391 (4)	C25—H25B	0.9800
C12—C15	1.490 (4)	C25—H25C	0.9800
C13—C14	1.382 (4)	O1W—H1A	0.8490
C13—H13	0.9500	O1W—H1B	0.8441
C14—H14	0.9500
N2—C1—N1	110.0 (3)	O2—C16—H16A	109.5
N2—C1—H1	125.0	O2—C16—H16B	109.5
N1—C1—H1	125.0	H16A—C16—H16B	109.5
C3—C2—C7	122.6 (3)	O2—C16—H16C	109.5
C3—C2—N1	106.3 (2)	H16A—C16—H16C	109.5
C7—C2—N1	131.1 (3)	H16B—C16—H16C	109.5
C2—C3—N2	106.8 (2)	N2—C17—C18	112.9 (2)
C2—C3—C4	121.4 (2)	N2—C17—H17A	109.0
N2—C3—C4	131.8 (2)	C18—C17—H17A	109.0
C5—C4—C3	115.9 (3)	N2—C17—H17B	109.0
C5—C4—H4	122.1	C18—C17—H17B	109.0
C3—C4—H4	122.1	H17A—C17—H17B	107.8
C4—C5—C6	122.8 (3)	C19—C18—C23	118.9 (3)
C4—C5—H5	118.6	C19—C18—C17	120.1 (3)
C6—C5—H5	118.6	C23—C18—C17	121.0 (3)
C7—C6—C5	121.4 (3)	C20—C19—C18	120.9 (3)
C7—C6—H6	119.3	C20—C19—H19	119.5
C5—C6—H6	119.3	C18—C19—H19	119.5
C6—C7—C2	116.0 (3)	C19—C20—C21	119.7 (3)
C6—C7—H7	122.0	C19—C20—H20	120.2
C2—C7—H7	122.0	C21—C20—H20	120.2
N1—C8—C9	115.1 (2)	C22—C21—C20	119.5 (3)
N1—C8—H8A	108.5	C22—C21—C24	118.6 (3)
C9—C8—H8A	108.5	C20—C21—C24	121.9 (3)
N1—C8—H8B	108.5	C23—C22—C21	120.7 (3)
C9—C8—H8B	108.5	C23—C22—H22	119.7
H8A—C8—H8B	107.5	C21—C22—H22	119.7
C10—C9—C14	119.1 (3)	C22—C23—C18	120.2 (3)
C10—C9—C8	123.8 (3)	C22—C23—H23	119.9
C14—C9—C8	117.1 (2)	C18—C23—H23	119.9
C11—C10—C9	120.0 (3)	O3—C24—O4	123.7 (3)
C11—C10—H10	120.0	O3—C24—C21	124.2 (3)
C9—C10—H10	120.0	O4—C24—C21	112.2 (3)
C10—C11—C12	121.1 (3)	O4—C25—H25A	109.5
C10—C11—H11	119.4	O4—C25—H25B	109.5
C12—C11—H11	119.4	H25A—C25—H25B	109.5
C11—C12—C13	119.0 (3)	O4—C25—H25C	109.5
C11—C12—C15	118.9 (3)	H25A—C25—H25C	109.5
C13—C12—C15	122.1 (3)	H25B—C25—H25C	109.5
C14—C13—C12	119.8 (3)	C1—N1—C2	108.3 (2)
C14—C13—H13	120.1	C1—N1—C8	125.2 (2)
C12—C13—H13	120.1	C2—N1—C8	126.1 (2)
C13—C14—C9	121.0 (3)	C1—N2—C3	108.5 (2)
C13—C14—H14	119.5	C1—N2—C17	124.8 (2)
C9—C14—H14	119.5	C3—N2—C17	126.5 (2)
O1—C15—O2	123.5 (3)	C15—O2—C16	115.7 (2)
O1—C15—C12	124.8 (3)	C24—O4—C25	115.3 (3)
O2—C15—C12	111.6 (2)	H1A—O1W—H1B	109.6
C7—C2—C3—N2	−178.0 (2)	C19—C20—C21—C22	−0.9 (4)
N1—C2—C3—N2	0.9 (3)	C19—C20—C21—C24	178.2 (3)
C7—C2—C3—C4	0.5 (4)	C20—C21—C22—C23	1.1 (4)
N1—C2—C3—C4	179.4 (2)	C24—C21—C22—C23	−178.0 (3)
C2—C3—C4—C5	−0.1 (4)	C21—C22—C23—C18	−0.6 (4)
N2—C3—C4—C5	177.9 (3)	C19—C18—C23—C22	−0.2 (4)
C3—C4—C5—C6	−0.2 (4)	C17—C18—C23—C22	179.8 (3)
C4—C5—C6—C7	0.2 (4)	C22—C21—C24—O3	−5.4 (5)
C5—C6—C7—C2	0.1 (4)	C20—C21—C24—O3	175.5 (3)
C3—C2—C7—C6	−0.4 (4)	C22—C21—C24—O4	173.7 (3)
N1—C2—C7—C6	−179.1 (3)	C20—C21—C24—O4	−5.3 (4)
N1—C8—C9—C10	−20.6 (4)	N2—C1—N1—C2	0.5 (3)
N1—C8—C9—C14	161.6 (3)	N2—C1—N1—C8	173.9 (2)
C14—C9—C10—C11	−0.4 (4)	C3—C2—N1—C1	−0.9 (3)
C8—C9—C10—C11	−178.1 (3)	C7—C2—N1—C1	177.9 (3)
C9—C10—C11—C12	0.1 (4)	C3—C2—N1—C8	−174.2 (2)
C10—C11—C12—C13	1.0 (4)	C7—C2—N1—C8	4.6 (5)
C10—C11—C12—C15	−178.0 (3)	C9—C8—N1—C1	108.2 (3)
C11—C12—C13—C14	−1.8 (4)	C9—C8—N1—C2	−79.5 (3)
C15—C12—C13—C14	177.2 (3)	N1—C1—N2—C3	0.1 (3)
C12—C13—C14—C9	1.6 (5)	N1—C1—N2—C17	−176.2 (2)
C10—C9—C14—C13	−0.5 (4)	C2—C3—N2—C1	−0.7 (3)
C8—C9—C14—C13	177.4 (3)	C4—C3—N2—C1	−178.9 (3)
C11—C12—C15—O1	4.8 (4)	C2—C3—N2—C17	175.5 (2)
C13—C12—C15—O1	−174.2 (3)	C4—C3—N2—C17	−2.7 (5)
C11—C12—C15—O2	−177.2 (2)	C18—C17—N2—C1	−86.9 (3)
C13—C12—C15—O2	3.9 (4)	C18—C17—N2—C3	97.5 (3)
N2—C17—C18—C19	83.0 (3)	O1—C15—O2—C16	−6.2 (4)
N2—C17—C18—C23	−96.9 (3)	C12—C15—O2—C16	175.7 (2)
C23—C18—C19—C20	0.4 (4)	O3—C24—O4—C25	2.5 (5)
C17—C18—C19—C20	−179.6 (3)	C21—C24—O4—C25	−176.6 (3)
C18—C19—C20—C21	0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1W	0.95	2.14	3.083 (3)	175.
O1W—H1A···Br1	0.85	2.49	3.332 (2)	173.
O1W—H1B···Br1i	0.84	2.43	3.269 (2)	173.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1W	0.95	2.14	3.083 (3)	175
O1W—H1A⋯Br1	0.85	2.49	3.332 (2)	173
O1W—H1B⋯Br1i	0.84	2.43	3.269 (2)	173

Symmetry code: (i) .