Ethyl 2-(4-bromophenyl)-1-[3-(1H-imidazol-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate monohydrate

Yoon, Y.K.; Ali, M.A.; Choon, T.S.; Hemamalini, M.; Fun, H.-K.

doi:10.1107/S160053681104342X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3060

doi:10.1107/S160053681104342X

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Ethyl 2-(4-bromophenyl)-1-[3-(1H-imidazol-1-yl)propyl]-1H-benzimidazole-5-carboxylate monohydrate

Yeong Keng Yoon,^a Mohamed Ashraf Ali,^a Tan Soo Choon,^a Madhukar Hemamalini ^b and Hoong-Kun Fun ^b ^*‡

^aInstitute for Research in Molecular Medicine, 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 18 October 2011; accepted 19 October 2011; online 29 October 2011)

In the title compound, C₂₂H₂₁BrN₄O₂·H₂O, the two pyrazole rings are essentially planar [maximum deviations 0.002 (1) and 0.002 (1) Å], and form a dihedral angle of 73.46 (9)°. The dihedral angle between the benzene rings is 29.33 (7)°. In the crystal, molecules are connected via C—H⋯O and O—H⋯N hydrogen bonds, forming layers in the ab plane.

Related literature

For applications of benzimidazole derivatives, see: Garuti et al. (2000 ); Rao et al. (2002 ); Thakurdesai et al. (2007 ); Yoon et al. (2011 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₂H₂₁BrN₄O₂·H₂O
M_r = 471.35
Monoclinic, P 2₁ /n
a = 9.1854 (1) Å
b = 16.7389 (2) Å
c = 13.7379 (2) Å
β = 98.283 (1)°
V = 2090.22 (5) Å³
Z = 4
Mo Kα radiation
μ = 2.00 mm⁻¹
T = 100 K
0.47 × 0.42 × 0.41 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.452, T_max = 0.494
28847 measured reflections
7482 independent reflections
5514 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.085
S = 1.03
7482 reflections
280 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2W1⋯N4ⁱ	0.92 (3)	1.99 (3)	2.910 (2)	175 (3)
O1W—H1W1⋯N1ⁱⁱ	0.81 (3)	2.16 (3)	2.891 (2)	151 (2)
C17—H17B⋯O1Wⁱⁱⁱ	0.99	2.41	3.236 (2)	141
C19—H19B⋯O1Wⁱⁱⁱ	0.99	2.56	3.327 (2)	135
C20—H20A⋯O2^iv	0.95	2.58	3.301 (2)	133
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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/S160053681104342X/tk5002sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681104342X/tk5002Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681104342X/tk5002Isup3.cml

checkCIF report

Comment top

Benzimidazole derivatives are of wide interest because of their diverse biological activities and various clinical applications. Benzimidazoles are a class of bioactive heterocyclic compounds which exhibit a wide range of activities such as anti-proliferative (Garuti et al., 2000), anti-HIV (Rao et al., 2002), anti-inflammatory and anthelmintic (Thakurdesai et al., 2007) properties. As part of our on-going structural studies of benzimidazole derivatives (Yoon et al., 2011), we now report the structure of the title compound.

In the title compound (Fig. 1), the two pyrazole (N1,N2/C7,C8/C13 and N3,N4/C20–C22) rings are essentially planar, with a maximum deviation of 0.002 (1) Å for atom C8 and 0.002 (1) Å for atom N3. The dihedral angle between the two pyrazole (N1,N2/C7,C8/C13 : N3,N4/C20–C22) rings is 73.46 (9)° and between the two benzene (C8–C13 : C1–C6) rings is 29.33 (7)°.

In the crystal structure, molecules are connected via intermolecular C—H···O and O—H···N (Table 1) hydrogen bonds, forming layers in the ab plane.

Related literature top

For applications of benzimidazole derivatives, see: Garuti et al. (2000); Rao et al. (2002); Thakurdesai et al. (2007); Yoon et al. (2011). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

Ethyl-4-(3-(1H-imidazol-1-yl-propylamino)-3-aminobenzoate (0.84 mmol) and sodium metabisulfite adduct of bromobenzaldehyde (1.68 mmol) were dissolved in DMF. The reaction mixture was refluxed at 130°C for 2 h. After completion, the reaction mixture was diluted in ethyl acetate (20 ml) and washed with water (20 ml). The organic layer was collected, dried over Na₂SO₄ and then evaporated in vacuo to yield the product. The product was recrystallised from its ethyl acetate solution.

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.

Ethyl 2-(4-bromophenyl)-1-[3-(1H-imidazol-1-yl)propyl]- 1H-benzimidazole-5-carboxylate monohydrate top

Crystal data top

C₂₂H₂₁BrN₄O₂·H₂O	F(000) = 968
M_r = 471.35	D_x = 1.498 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9939 reflections
a = 9.1854 (1) Å	θ = 2.5–31.3°
b = 16.7389 (2) Å	µ = 2.00 mm⁻¹
c = 13.7379 (2) Å	T = 100 K
β = 98.283 (1)°	Block, yellow
V = 2090.22 (5) Å³	0.47 × 0.42 × 0.41 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7482 independent reflections
Radiation source: fine-focus sealed tube	5514 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 32.4°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
T_min = 0.452, T_max = 0.494	k = −25→17
28847 measured reflections	l = −20→19

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0386P)² + 0.518P] where P = (F_o² + 2F_c²)/3
7482 reflections	(Δ/σ)_max = 0.001
280 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₂₂H₂₁BrN₄O₂·H₂O	V = 2090.22 (5) Å³
M_r = 471.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.1854 (1) Å	µ = 2.00 mm⁻¹
b = 16.7389 (2) Å	T = 100 K
c = 13.7379 (2) Å	0.47 × 0.42 × 0.41 mm
β = 98.283 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7482 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5514 reflections with I > 2σ(I)
T_min = 0.452, T_max = 0.494	R_int = 0.032
28847 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.63 e Å⁻³
7482 reflections	Δρ_min = −0.34 e Å⁻³
280 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
Br1	0.123446 (18)	0.050021 (9)	0.931417 (13)	0.02720 (6)
O1	0.40323 (12)	0.80153 (6)	0.87745 (9)	0.0247 (2)
O2	0.17930 (13)	0.76409 (7)	0.90802 (9)	0.0260 (2)
N1	0.23105 (14)	0.45313 (7)	0.89922 (10)	0.0199 (3)
N2	0.46106 (14)	0.42561 (7)	0.87069 (9)	0.0174 (2)
N3	0.71289 (14)	0.23427 (8)	0.76584 (10)	0.0216 (3)
N4	0.61875 (16)	0.11193 (8)	0.75103 (11)	0.0265 (3)
C1	0.18138 (17)	0.29413 (9)	0.95735 (11)	0.0207 (3)
H1A	0.1411	0.3363	0.9913	0.025*
C2	0.13384 (17)	0.21676 (9)	0.96832 (12)	0.0209 (3)
H2A	0.0622	0.2056	1.0099	0.025*
C3	0.19242 (17)	0.15558 (9)	0.91768 (11)	0.0197 (3)
C4	0.29838 (17)	0.17037 (9)	0.85769 (12)	0.0212 (3)
H4A	0.3385	0.1279	0.8242	0.025*
C5	0.34509 (17)	0.24861 (9)	0.84737 (11)	0.0201 (3)
H5A	0.4170	0.2595	0.8059	0.024*
C6	0.28788 (16)	0.31134 (8)	0.89703 (11)	0.0174 (3)
C7	0.32652 (16)	0.39632 (9)	0.88789 (11)	0.0181 (3)
C8	0.44933 (16)	0.50829 (8)	0.87200 (11)	0.0175 (3)
C9	0.54989 (17)	0.56882 (9)	0.86054 (12)	0.0207 (3)
H9A	0.6473	0.5574	0.8490	0.025*
C10	0.50014 (17)	0.64649 (9)	0.86687 (11)	0.0204 (3)
H10A	0.5648	0.6895	0.8589	0.025*
C11	0.35573 (17)	0.66335 (8)	0.88480 (11)	0.0188 (3)
C12	0.25683 (17)	0.60237 (9)	0.89609 (11)	0.0201 (3)
H12A	0.1595	0.6137	0.9078	0.024*
C13	0.30541 (16)	0.52409 (9)	0.88960 (11)	0.0186 (3)
C14	0.30222 (17)	0.74678 (9)	0.89169 (11)	0.0209 (3)
C15	0.35706 (19)	0.88442 (9)	0.88439 (14)	0.0271 (4)
H15A	0.3201	0.8936	0.9477	0.033*
H15B	0.2771	0.8970	0.8302	0.033*
C16	0.4876 (2)	0.93640 (10)	0.87762 (16)	0.0345 (4)
H16A	0.4609	0.9924	0.8859	0.052*
H16B	0.5196	0.9293	0.8131	0.052*
H16C	0.5679	0.9215	0.9294	0.052*
C17	0.59623 (16)	0.38267 (9)	0.85909 (11)	0.0186 (3)
H17A	0.5934	0.3290	0.8891	0.022*
H17B	0.6814	0.4118	0.8948	0.022*
C18	0.61756 (17)	0.37351 (9)	0.75149 (12)	0.0209 (3)
H18A	0.5262	0.3523	0.7132	0.025*
H18B	0.6376	0.4265	0.7242	0.025*
C19	0.74492 (18)	0.31714 (9)	0.74141 (13)	0.0241 (3)
H19A	0.7669	0.3193	0.6730	0.029*
H19B	0.8335	0.3354	0.7854	0.029*
C20	0.62362 (17)	0.18286 (9)	0.70936 (12)	0.0223 (3)
H20A	0.5706	0.1962	0.6469	0.027*
C21	0.7101 (2)	0.11857 (11)	0.83933 (14)	0.0318 (4)
H21A	0.7297	0.0769	0.8864	0.038*
C22	0.76797 (19)	0.19311 (11)	0.84941 (13)	0.0310 (4)
H22A	0.8338	0.2130	0.9037	0.037*
O1W	0.41413 (16)	0.03202 (9)	0.36883 (13)	0.0409 (4)
H2W1	0.406 (4)	−0.015 (2)	0.334 (2)	0.092 (10)*
H1W1	0.496 (3)	0.0391 (14)	0.3976 (19)	0.052 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02447 (9)	0.01647 (7)	0.04180 (11)	−0.00321 (6)	0.00871 (7)	0.00484 (6)
O1	0.0236 (6)	0.0141 (5)	0.0369 (7)	−0.0002 (4)	0.0064 (5)	0.0000 (4)
O2	0.0224 (6)	0.0207 (5)	0.0355 (7)	0.0011 (4)	0.0059 (5)	−0.0032 (5)
N1	0.0168 (6)	0.0168 (6)	0.0267 (7)	−0.0011 (5)	0.0054 (5)	0.0010 (5)
N2	0.0152 (6)	0.0147 (5)	0.0232 (6)	−0.0008 (4)	0.0056 (5)	0.0004 (5)
N3	0.0179 (6)	0.0207 (6)	0.0270 (7)	0.0007 (5)	0.0065 (5)	−0.0022 (5)
N4	0.0254 (7)	0.0227 (7)	0.0324 (8)	0.0012 (5)	0.0077 (6)	0.0011 (6)
C1	0.0190 (7)	0.0200 (7)	0.0239 (8)	−0.0014 (6)	0.0056 (6)	−0.0009 (6)
C2	0.0179 (7)	0.0215 (7)	0.0239 (8)	−0.0016 (6)	0.0054 (6)	0.0029 (6)
C3	0.0187 (7)	0.0157 (6)	0.0245 (8)	−0.0022 (5)	0.0025 (6)	0.0041 (6)
C4	0.0213 (8)	0.0178 (7)	0.0250 (8)	0.0001 (6)	0.0051 (6)	0.0002 (6)
C5	0.0190 (7)	0.0193 (7)	0.0232 (8)	−0.0012 (5)	0.0070 (6)	0.0010 (6)
C6	0.0158 (7)	0.0170 (6)	0.0197 (7)	−0.0021 (5)	0.0032 (5)	0.0013 (5)
C7	0.0178 (7)	0.0172 (6)	0.0198 (7)	−0.0014 (5)	0.0039 (5)	0.0003 (5)
C8	0.0180 (7)	0.0149 (6)	0.0199 (7)	−0.0001 (5)	0.0039 (5)	−0.0004 (5)
C9	0.0176 (7)	0.0197 (7)	0.0255 (8)	−0.0019 (5)	0.0056 (6)	0.0000 (6)
C10	0.0205 (7)	0.0174 (6)	0.0237 (8)	−0.0035 (6)	0.0042 (6)	0.0011 (6)
C11	0.0199 (7)	0.0164 (6)	0.0199 (7)	−0.0001 (5)	0.0023 (6)	−0.0006 (5)
C12	0.0169 (7)	0.0196 (7)	0.0238 (8)	0.0003 (5)	0.0031 (6)	0.0003 (6)
C13	0.0166 (7)	0.0172 (6)	0.0221 (7)	−0.0019 (5)	0.0035 (6)	0.0008 (5)
C14	0.0214 (8)	0.0186 (7)	0.0221 (8)	−0.0010 (6)	0.0007 (6)	−0.0014 (6)
C15	0.0292 (9)	0.0142 (7)	0.0384 (10)	0.0025 (6)	0.0062 (7)	−0.0004 (6)
C16	0.0313 (10)	0.0184 (8)	0.0557 (12)	−0.0001 (6)	0.0127 (9)	−0.0008 (7)
C17	0.0162 (7)	0.0175 (6)	0.0229 (7)	0.0004 (5)	0.0055 (6)	0.0002 (5)
C18	0.0208 (7)	0.0183 (7)	0.0250 (8)	−0.0012 (6)	0.0079 (6)	−0.0007 (6)
C19	0.0208 (8)	0.0213 (7)	0.0325 (9)	−0.0039 (6)	0.0113 (6)	−0.0039 (6)
C20	0.0211 (8)	0.0215 (7)	0.0250 (8)	−0.0002 (6)	0.0063 (6)	−0.0018 (6)
C21	0.0301 (9)	0.0293 (9)	0.0351 (10)	0.0053 (7)	0.0013 (8)	0.0065 (7)
C22	0.0259 (9)	0.0338 (9)	0.0313 (9)	0.0032 (7)	−0.0027 (7)	0.0001 (7)
O1W	0.0218 (7)	0.0354 (8)	0.0648 (10)	0.0047 (6)	0.0035 (7)	−0.0090 (7)

Geometric parameters (Å, º) top

Br1—C3	1.8957 (14)	C9—H9A	0.9500
O1—C14	1.3384 (19)	C10—C11	1.412 (2)
O1—C15	1.4579 (18)	C10—H10A	0.9500
O2—C14	1.2174 (19)	C11—C12	1.390 (2)
N1—C7	1.3179 (19)	C11—C14	1.488 (2)
N1—C13	1.3860 (18)	C12—C13	1.391 (2)
N2—C7	1.3811 (19)	C12—H12A	0.9500
N2—C8	1.3884 (18)	C15—C16	1.495 (2)
N2—C17	1.4630 (19)	C15—H15A	0.9900
N3—C20	1.353 (2)	C15—H15B	0.9900
N3—C22	1.372 (2)	C16—H16A	0.9800
N3—C19	1.4668 (19)	C16—H16B	0.9800
N4—C20	1.322 (2)	C16—H16C	0.9800
N4—C21	1.376 (2)	C17—C18	1.527 (2)
C1—C2	1.382 (2)	C17—H17A	0.9900
C1—C6	1.400 (2)	C17—H17B	0.9900
C1—H1A	0.9500	C18—C19	1.525 (2)
C2—C3	1.389 (2)	C18—H18A	0.9900
C2—H2A	0.9500	C18—H18B	0.9900
C3—C4	1.385 (2)	C19—H19A	0.9900
C4—C5	1.392 (2)	C19—H19B	0.9900
C4—H4A	0.9500	C20—H20A	0.9500
C5—C6	1.396 (2)	C21—C22	1.355 (3)
C5—H5A	0.9500	C21—H21A	0.9500
C6—C7	1.476 (2)	C22—H22A	0.9500
C8—C9	1.395 (2)	O1W—H2W1	0.92 (3)
C8—C13	1.403 (2)	O1W—H1W1	0.80 (3)
C9—C10	1.385 (2)

C14—O1—C15	115.33 (12)	N1—C13—C8	110.14 (13)
C7—N1—C13	105.17 (13)	C12—C13—C8	120.50 (14)
C7—N2—C8	106.18 (12)	O2—C14—O1	123.01 (14)
C7—N2—C17	129.68 (12)	O2—C14—C11	123.97 (14)
C8—N2—C17	124.04 (12)	O1—C14—C11	113.02 (13)
C20—N3—C22	106.29 (14)	O1—C15—C16	107.83 (14)
C20—N3—C19	126.52 (14)	O1—C15—H15A	110.1
C22—N3—C19	127.19 (14)	C16—C15—H15A	110.1
C20—N4—C21	104.76 (14)	O1—C15—H15B	110.1
C2—C1—C6	121.07 (15)	C16—C15—H15B	110.1
C2—C1—H1A	119.5	H15A—C15—H15B	108.5
C6—C1—H1A	119.5	C15—C16—H16A	109.5
C1—C2—C3	119.01 (15)	C15—C16—H16B	109.5
C1—C2—H2A	120.5	H16A—C16—H16B	109.5
C3—C2—H2A	120.5	C15—C16—H16C	109.5
C4—C3—C2	121.48 (14)	H16A—C16—H16C	109.5
C4—C3—Br1	119.95 (12)	H16B—C16—H16C	109.5
C2—C3—Br1	118.56 (12)	N2—C17—C18	112.59 (12)
C3—C4—C5	118.83 (14)	N2—C17—H17A	109.1
C3—C4—H4A	120.6	C18—C17—H17A	109.1
C5—C4—H4A	120.6	N2—C17—H17B	109.1
C4—C5—C6	120.99 (14)	C18—C17—H17B	109.1
C4—C5—H5A	119.5	H17A—C17—H17B	107.8
C6—C5—H5A	119.5	C19—C18—C17	110.93 (13)
C5—C6—C1	118.62 (13)	C19—C18—H18A	109.5
C5—C6—C7	124.85 (14)	C17—C18—H18A	109.5
C1—C6—C7	116.47 (13)	C19—C18—H18B	109.5
N1—C7—N2	113.02 (13)	C17—C18—H18B	109.5
N1—C7—C6	120.87 (13)	H18A—C18—H18B	108.0
N2—C7—C6	126.07 (13)	N3—C19—C18	112.50 (13)
N2—C8—C9	131.96 (14)	N3—C19—H19A	109.1
N2—C8—C13	105.48 (12)	C18—C19—H19A	109.1
C9—C8—C13	122.55 (13)	N3—C19—H19B	109.1
C10—C9—C8	116.42 (14)	C18—C19—H19B	109.1
C10—C9—H9A	121.8	H19A—C19—H19B	107.8
C8—C9—H9A	121.8	N4—C20—N3	112.23 (15)
C9—C10—C11	121.69 (14)	N4—C20—H20A	123.9
C9—C10—H10A	119.2	N3—C20—H20A	123.9
C11—C10—H10A	119.2	C22—C21—N4	110.16 (15)
C12—C11—C10	121.21 (14)	C22—C21—H21A	124.9
C12—C11—C14	117.06 (14)	N4—C21—H21A	124.9
C10—C11—C14	121.73 (13)	C21—C22—N3	106.55 (15)
C11—C12—C13	117.63 (14)	C21—C22—H22A	126.7
C11—C12—H12A	121.2	N3—C22—H22A	126.7
C13—C12—H12A	121.2	H2W1—O1W—H1W1	113 (3)
N1—C13—C12	129.35 (14)

C6—C1—C2—C3	−0.6 (2)	C14—C11—C12—C13	179.87 (13)
C1—C2—C3—C4	0.8 (2)	C7—N1—C13—C12	−179.26 (15)
C1—C2—C3—Br1	−178.80 (11)	C7—N1—C13—C8	0.03 (17)
C2—C3—C4—C5	−0.9 (2)	C11—C12—C13—N1	179.06 (15)
Br1—C3—C4—C5	178.77 (11)	C11—C12—C13—C8	−0.2 (2)
C3—C4—C5—C6	0.6 (2)	N2—C8—C13—N1	0.23 (16)
C4—C5—C6—C1	−0.4 (2)	C9—C8—C13—N1	−179.16 (14)
C4—C5—C6—C7	−177.66 (14)	N2—C8—C13—C12	179.59 (13)
C2—C1—C6—C5	0.3 (2)	C9—C8—C13—C12	0.2 (2)
C2—C1—C6—C7	177.85 (13)	C15—O1—C14—O2	1.0 (2)
C13—N1—C7—N2	−0.29 (17)	C15—O1—C14—C11	−179.41 (13)
C13—N1—C7—C6	177.75 (13)	C12—C11—C14—O2	1.2 (2)
C8—N2—C7—N1	0.43 (17)	C10—C11—C14—O2	−179.21 (15)
C17—N2—C7—N1	176.78 (14)	C12—C11—C14—O1	−178.39 (13)
C8—N2—C7—C6	−177.48 (14)	C10—C11—C14—O1	1.2 (2)
C17—N2—C7—C6	−1.1 (2)	C14—O1—C15—C16	173.90 (14)
C5—C6—C7—N1	150.20 (15)	C7—N2—C17—C18	100.34 (17)
C1—C6—C7—N1	−27.1 (2)	C8—N2—C17—C18	−83.90 (17)
C5—C6—C7—N2	−32.0 (2)	N2—C17—C18—C19	−170.67 (12)
C1—C6—C7—N2	150.63 (15)	C20—N3—C19—C18	75.0 (2)
C7—N2—C8—C9	178.93 (16)	C22—N3—C19—C18	−105.67 (18)
C17—N2—C8—C9	2.3 (2)	C17—C18—C19—N3	68.15 (17)
C7—N2—C8—C13	−0.38 (15)	C21—N4—C20—N3	0.10 (19)
C17—N2—C8—C13	−176.99 (13)	C22—N3—C20—N4	−0.28 (19)
N2—C8—C9—C10	−179.58 (15)	C19—N3—C20—N4	179.12 (14)
C13—C8—C9—C10	−0.4 (2)	C20—N4—C21—C22	0.1 (2)
C8—C9—C10—C11	0.5 (2)	N4—C21—C22—N3	−0.3 (2)
C9—C10—C11—C12	−0.5 (2)	C20—N3—C22—C21	0.35 (19)
C9—C10—C11—C14	179.95 (14)	C19—N3—C22—C21	−179.05 (15)
C10—C11—C12—C13	0.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W1···N4ⁱ	0.92 (3)	1.99 (3)	2.910 (2)	175 (3)
O1W—H1W1···N1ⁱⁱ	0.81 (3)	2.16 (3)	2.891 (2)	151 (2)
C17—H17B···O1Wⁱⁱⁱ	0.99	2.41	3.236 (2)	141
C19—H19B···O1Wⁱⁱⁱ	0.99	2.56	3.327 (2)	135
C20—H20A···O2^iv	0.95	2.58	3.301 (2)	133

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

Experimental details

Crystal data
Chemical formula	C₂₂H₂₁BrN₄O₂·H₂O
M_r	471.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	9.1854 (1), 16.7389 (2), 13.7379 (2)
β (°)	98.283 (1)
V (Å³)	2090.22 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.00
Crystal size (mm)	0.47 × 0.42 × 0.41

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.452, 0.494
No. of measured, independent and observed [I > 2σ(I)] reflections	28847, 7482, 5514
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.754

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.085, 1.03
No. of reflections	7482
No. of parameters	280
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.34

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—H2W1···N4ⁱ	0.92 (3)	1.99 (3)	2.910 (2)	175 (3)
O1W—H1W1···N1ⁱⁱ	0.81 (3)	2.16 (3)	2.891 (2)	151 (2)
C17—H17B···O1Wⁱⁱⁱ	0.9900	2.4100	3.236 (2)	141.00
C19—H19B···O1Wⁱⁱⁱ	0.9900	2.5600	3.327 (2)	135.00
C20—H20A···O2^iv	0.9500	2.5800	3.301 (2)	133.00

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

YKY, MAA and TSC thank the Department of Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Molecular Medicine, Universiti Sains Malaysia, Penang. This work was funded through a Research Grant (No. RUC 1001/PSK/8620012). HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for a Research University grant (No. 1001/PFIZIK/811160). MH thanks Universiti Sains Malaysia for a postdoctoral research fellowship.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Garuti, L., Roberti, M., Malagoli, M., Rossi, T. & Castelli, M. (2000). Bioorg. Med. Chem. Lett. 10, 2193–2195. Web of Science CrossRef PubMed CAS Google Scholar
Rao, A., Chimirri, A., Clercq, E. D., Monforte, A. M., Monforte, P., Pannecouque, C. & Zappala, M. (2002). Il Farmaco, 57, 819–823. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thakurdesai, P. A., Wadodkar, S. G. & Chopade, C. T. (2007). Pharmacologyonline, 1, 314–329. Google Scholar
Yoon, Y. K., Ali, M. A., Wei, A. C., Quah, C. K. & Fun, H.-K. (2011). Acta Cryst. E67, o2405. Web of Science CSD CrossRef IUCr Journals Google Scholar

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

Ethyl 2-(4-bromo­phenyl)-1-[3-(1H-imidazol-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

Ethyl 2-(4-bromophenyl)-1-[3-(1H-imidazol-1-yl)propyl]-1H-benzimidazole-5-carboxylate monohydrate