(2E)-3-{4-[(1H-1,3-Benzimidazol-2-yl)meth­oxy]-3-eth­oxy­phen­yl}-1-(4-bromo­phen­yl)prop-2-en-1-one monohydrate

Jasinski, J.P.; Miller, W.M.; Samshuddin, S.; Narayana, B.; Yathirajan, H.S.

doi:10.1107/S1600536811008154

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Pages o834-o835

doi:10.1107/S1600536811008154

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(2E)-3-{4-[(1H-1,3-Benzimidazol-2-yl)methoxy]-3-ethoxyphenyl}-1-(4-bromophenyl)prop-2-en-1-one monohydrate

Jerry P. Jasinski,^a ^* William M. Miller,^a S. Samshuddin,^b B. Narayana ^b and H. S. Yathirajan ^c

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 30 January 2011; accepted 3 March 2011; online 12 March 2011)

In the title compound, C₂₅H₂₁BrN₂O₃·H₂O, the benzimidazole fragment and the water molecule of crystallization are each disordered over two sets of sites of equal occupancy. The dihedral angles between the least-squares planes of the benzimidazole and the 3-ethoxy- and 4-bromobenzene rings are 86.9 (6) and 85.1 (1)°, respectively in one disorder component. The crystal packing is stabilized by intermolecular O—H⋯O, O—H⋯N and N—H⋯N hydrogen bonds, which link the molecules into chains along the a axis.

Related literature

For the biological activity of benzimidazoles, see: Pujar et al. (1988 ); Bouwman et al. (1990 ). For the use of benzimidazoles in pest control, see: Madkour et al. (2006 ). For the properties and uses of chalcones, see: Dhar (1981 ); Dimmock et al. (1999 ); Satyanarayana et al. (2004 ); Sarojini et al. (2006 ). For related structures, see: Jian et al. (2003 ); Odabaşoğlu et al. (2007 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₅H₂₁BrN₂O₃·H₂O
M_r = 495.36
Orthorhombic, P b c n
a = 13.8406 (12) Å
b = 16.5192 (8) Å
c = 19.4719 (13) Å
V = 4452.0 (5) Å³
Z = 8
Mo Kα radiation
μ = 1.88 mm⁻¹
T = 295 K
0.52 × 0.38 × 0.31 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.518, T_max = 1.000
18755 measured reflections
4033 independent reflections
2083 reflections with I > 2σ(I)
R_int = 0.073

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.160
S = 1.04
4033 reflections
305 parameters
114 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯N2Bⁱ	0.86	2.10	2.908 (9)	157
N2B—H2BA⋯N2ⁱ	0.86	2.06	2.908 (9)	172
O1WA—H1W1⋯O1WAⁱⁱ	0.82 (2)	1.89 (3)	2.69 (2)	164 (7)
O1WA—H1W2⋯N1	0.82 (2)	1.87 (2)	2.674 (16)	166 (6)
O1WA—H1W2⋯N1B	0.82 (2)	2.20 (3)	2.997 (17)	164 (6)
O1WB—H1W4⋯O1ⁱⁱⁱ	0.82 (2)	2.33 (7)	2.912 (11)	129 (8)
Symmetry codes: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008154/ez2232sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811008154/ez2232Isup2.hkl

checkCIF report

Comment top

The benzimidazole ring system and its related compounds play an important role in pharmaceutical and agricultural fields due to their broad spectrum of biological activities (Pujar et al., 1988, Bouwman et al., 1990). The synthesis of novel benzimidazole derivatives remains a main focus of medicinal research. Benzimidazoles are also useful as insecticides, acaricides, nematocides, herbicides and other plant-protective agents in the field of pest control (Madkour et al., 2006). In recent years, attention has increasingly been given to the synthesis of benzimidazole derivatives as a source of new antimicrobial agents. In addition, benzimidazole derivatives have played a crucial role in the theoretical development of heterocyclic chemistry and are also used extensively in organic synthesis.

Chalcones constitute an important family of substances belonging to the flavonoids, a large group of natural and synthetic products with interesting physicochemical properties, biological activities and structural characteristics. Chalcones are highly reactive substances of varied nature. They have been reported to possess many interesting pharmacological activities (Dhar, 1981) including anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor and anticancer activities (Dimmock et al., 1999; Satyanarayana et al., 2004). Chalcones are also finding application as organic nonlinear optical materials (NLO) for their SHG conversion efficiency (Sarojini et al., 2006).

The crystal structures of some benzimidazole derivatives viz., 2-chloromethyl-1H-benzimidazole nitrate (Jian et al., 2003) and 5-methoxy-1H-benzo[d]imidazole-2(3H)-thione (Odabaşoğlu et al., 2007) have been reported. Encouraged by the diverse biological activities of benzimidazoles and chalcones, it was decided to prepare a new chalcone derivative of 2-aryloxy methylbenzimidazole, thus bringing both types of functional groups together in a single molecule. This paper reports the crystal structure of the title compound, C₂₅H₂₁N₂O₃Br. H₂O, (I).

In the title compound, (I), the benzimidazole fragment and an associated water molecule are each disordered over two positions in a ratio of 0.50 (0) and 0.50 (0) (Fig. 2). The dihedral angles between the least squares planes of the benzimidazol (0.50 (0) component) and the 3-ethoxy and 4-bromo benzene rings are 86.9 (6)° and 85.1 (1)°, respectively (Fig. 3). Bond distances and angles are in normal ranges (Allen et al., 1987). Crystal packing is stabilized by O—H···O, N—H···O and N—H···N intermolecular hydrogen bonds (Table 1) linking the molecules into one-dimensional chains along the a axis (Fig. 4).

Related literature top

For the biological activity of benzimidazoles, see: Pujar et al. (1988); Bouwman et al. (1990). For the use of benzimidazoles in pest control, see: Madkour et al. (2006). For the properties and uses of chalcones, see: Dhar (1981); Dimmock et al. (1999); Satyanarayana et al. (2004); Sarojini et al. (2006). For related structures, see: Jian et al. (2003); Odabaşoğlu et al. (2007). For standard bond lengths, see: Allen et al. (1987). [Author: scheme should show solvent molecule]

Experimental top

A mixture of a 4-(1H-benzimidazol-2-ylmethoxy)-3-ethoxybenzaldehyde (0.005 mole) and p-bromo acetophenone (0.005 mole) in 50 ml ethanolic sodium hydroxide was stirred at 5–10°C for 3 h (Fig. 1), then maintained at room temperature for 24 h and poured into ice cold water. The precipitate that appeared after neutralization with dil. HCl was filtered off and recrystallized from 1,4-dioxane. The single crystals were grown from DMF by the slow evaporation method, with a yield of 85%. (m.p. 414 K). Analytical data: Found (Cald): C%: 62.89(62.90); H%: 4.39 (4.43); N%: 5.81 (5.87).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Reaction scheme for (I).
	Fig. 2. Molecular structure of the title compound showing the atom labeling scheme and 30% probability displacement ellipsoids. The disordered benzimidazol fragment has 0.50 (0) and 0.50 (0) occupancy components. Dashed lines indicate strong O—H···N intermolecular hydrogen bonds between O1WA and disordered N1 or N1B (0.50 (0) occupancy) atoms.
	Fig. 3. Packing diagram of the title compound viewed down the a axis. Dashed lines indicate N—H···N, O—H···O and O—H···N intermolecular hydrogen bonds linking the molecules into one-dimensional chains.

(2E)-3-{4-[(1H-1,3-Benzimidazol-2-yl)methoxy]-3-ethoxyphenyl}- 1-(4-bromophenyl)prop-2-en-1-one monohydrate top

Crystal data top

C₂₅H₂₁BrN₂O₃·H₂O	F(000) = 2032
M_r = 495.36	D_x = 1.478 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 4366 reflections
a = 13.8406 (12) Å	θ = 5.0–32.7°
b = 16.5192 (8) Å	µ = 1.88 mm⁻¹
c = 19.4719 (13) Å	T = 295 K
V = 4452.0 (5) Å³	Prism, pale yellow
Z = 8	0.52 × 0.38 × 0.31 mm

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	4033 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2083 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.073
Detector resolution: 10.5081 pixels mm^-1	θ_max = 25.4°, θ_min = 5.0°
ω scans	h = −16→12
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −19→19
T_min = 0.518, T_max = 1.000	l = −23→19
18755 measured reflections

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.068P)² + 2.7272P] where P = (F_o² + 2F_c²)/3
4033 reflections	(Δ/σ)_max < 0.001
305 parameters	Δρ_max = 0.46 e Å⁻³
114 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₂₅H₂₁BrN₂O₃·H₂O	V = 4452.0 (5) Å³
M_r = 495.36	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 13.8406 (12) Å	µ = 1.88 mm⁻¹
b = 16.5192 (8) Å	T = 295 K
c = 19.4719 (13) Å	0.52 × 0.38 × 0.31 mm

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	4033 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	2083 reflections with I > 2σ(I)
T_min = 0.518, T_max = 1.000	R_int = 0.073
18755 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	114 restraints
wR(F²) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.46 e Å⁻³
4033 reflections	Δρ_min = −0.36 e Å⁻³
305 parameters

Special details top

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	Occ. (<1)
Br1	0.36419 (4)	−0.33624 (3)	0.39000 (3)	0.0699 (2)
O1	0.3916 (3)	0.02167 (18)	0.55959 (18)	0.0678 (11)
O2	0.3780 (2)	0.45425 (15)	0.47027 (14)	0.0491 (8)
O3	0.3733 (3)	0.45641 (16)	0.33737 (14)	0.0564 (9)
C1	0.3652 (3)	−0.2277 (3)	0.4205 (2)	0.0483 (12)
C2	0.3675 (4)	−0.1650 (3)	0.3743 (3)	0.0595 (14)
H2A	0.3669	−0.1754	0.3274	0.071*
C3	0.3708 (4)	−0.0862 (3)	0.3983 (2)	0.0564 (14)
H3A	0.3717	−0.0436	0.3671	0.068*
C4	0.3727 (3)	−0.0700 (2)	0.4679 (2)	0.0440 (12)
C5	0.3679 (4)	−0.1340 (3)	0.5130 (2)	0.0579 (14)
H5A	0.3680	−0.1240	0.5600	0.069*
C6	0.3630 (4)	−0.2123 (3)	0.4897 (3)	0.0569 (14)
H6A	0.3582	−0.2548	0.5208	0.068*
C7	0.3810 (3)	0.0138 (3)	0.4975 (3)	0.0475 (12)
C8	0.3796 (3)	0.0841 (3)	0.4527 (3)	0.0532 (13)
H8A	0.3674	0.0767	0.4061	0.064*
C9	0.3949 (3)	0.1581 (2)	0.4756 (2)	0.0481 (12)
H9A	0.4073	0.1623	0.5225	0.058*
C10	0.3952 (3)	0.2344 (2)	0.4375 (2)	0.0443 (12)
C11	0.3915 (3)	0.3077 (2)	0.4727 (2)	0.0453 (12)
H11A	0.3936	0.3071	0.5204	0.054*
C12	0.3848 (3)	0.3807 (2)	0.4397 (2)	0.0422 (12)
C13	0.3839 (3)	0.3816 (3)	0.3674 (2)	0.0454 (12)
C14	0.3914 (4)	0.3099 (3)	0.3323 (2)	0.0606 (15)
H14A	0.3936	0.3107	0.2846	0.073*
C15	0.3957 (4)	0.2361 (3)	0.3664 (2)	0.0568 (14)
H15A	0.3989	0.1881	0.3416	0.068*
C16	0.3816 (4)	0.4565 (3)	0.5438 (2)	0.0559 (14)
H16A	0.4430	0.4355	0.5599	0.067*
H16B	0.3302	0.4235	0.5630	0.067*
C17	0.3696 (4)	0.5425 (3)	0.5656 (3)	0.0616 (15)
H17A	0.3617	0.5449	0.6146	0.092*
H17B	0.3137	0.5651	0.5437	0.092*
H17C	0.4259	0.5729	0.5526	0.092*
C18	0.3559 (4)	0.4556 (3)	0.2653 (2)	0.0596 (15)
H18A	0.3025	0.4195	0.2550	0.072*
H18B	0.4127	0.4361	0.2413	0.072*
C19	0.3322 (4)	0.5392 (3)	0.2419 (2)	0.0507 (13)
N1	0.2329 (9)	0.5577 (7)	0.2317 (6)	0.0470 (17)	0.50
N2	0.3896 (9)	0.5909 (8)	0.2252 (6)	0.0442 (16)	0.50
H2B	0.4515	0.5865	0.2258	0.053*	0.50
C20	0.3371 (4)	0.6595 (4)	0.2046 (4)	0.0440 (15)	0.50
C21	0.3602 (4)	0.7363 (4)	0.1805 (4)	0.058 (2)	0.50
H21A	0.4244	0.7528	0.1787	0.070*	0.50
C22	0.2874 (5)	0.7883 (4)	0.1589 (4)	0.048 (2)	0.50
H22A	0.3029	0.8397	0.1427	0.058*	0.50
C23	0.1915 (4)	0.7637 (4)	0.1615 (4)	0.049 (2)	0.50
H23A	0.1428	0.7985	0.1471	0.059*	0.50
C24	0.1684 (4)	0.6869 (4)	0.1857 (4)	0.055 (2)	0.50
H24A	0.1042	0.6704	0.1874	0.066*	0.50
C25	0.2412 (5)	0.6348 (4)	0.2072 (4)	0.0440 (15)	0.50
O1WA	0.0810 (8)	0.4606 (6)	0.2117 (5)	0.098 (2)	0.50
H1W1	0.036 (3)	0.468 (5)	0.239 (3)	0.148*	0.50
H1W2	0.121 (3)	0.495 (4)	0.222 (5)	0.148*	0.50
N1B	0.2526 (10)	0.5698 (8)	0.2266 (7)	0.0470 (17)	0.50
N2B	0.4086 (10)	0.5968 (8)	0.2335 (7)	0.0442 (16)	0.50
H2BA	0.4690	0.5911	0.2426	0.053*	0.50
C20B	0.3630 (5)	0.6620 (4)	0.2080 (4)	0.0440 (15)	0.50
C21B	0.3995 (4)	0.7368 (4)	0.1880 (4)	0.058 (2)	0.50
H21B	0.4656	0.7467	0.1903	0.070*	0.50
C22B	0.3372 (5)	0.7968 (4)	0.1647 (4)	0.048 (2)	0.50
H22B	0.3616	0.8469	0.1514	0.058*	0.50
C23B	0.2384 (5)	0.7820 (4)	0.1614 (4)	0.049 (2)	0.50
H23B	0.1967	0.8222	0.1458	0.059*	0.50
C24B	0.2020 (4)	0.7072 (5)	0.1813 (5)	0.055 (2)	0.50
H24B	0.1359	0.6973	0.1791	0.066*	0.50
C25B	0.2643 (5)	0.6472 (4)	0.2046 (4)	0.0440 (15)	0.50
O1WB	0.0642 (8)	0.5103 (6)	0.2033 (5)	0.098 (2)	0.50
H1W3	0.082 (6)	0.464 (2)	0.199 (4)	0.148*	0.50
H1W4	0.050 (8)	0.525 (5)	0.165 (2)	0.148*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0949 (4)	0.0427 (3)	0.0722 (4)	0.0038 (3)	0.0105 (3)	−0.0083 (3)
O1	0.104 (3)	0.0461 (19)	0.053 (2)	−0.0001 (19)	−0.008 (2)	0.0056 (16)
O2	0.081 (2)	0.0316 (15)	0.0344 (17)	0.0001 (15)	−0.0072 (17)	−0.0021 (13)
O3	0.102 (3)	0.0329 (15)	0.0340 (17)	−0.0041 (17)	−0.0102 (18)	0.0018 (13)
C1	0.060 (3)	0.036 (2)	0.049 (3)	0.000 (2)	0.017 (3)	0.001 (2)
C2	0.075 (4)	0.049 (3)	0.054 (3)	0.006 (3)	0.001 (3)	−0.002 (2)
C3	0.073 (4)	0.043 (2)	0.053 (3)	0.006 (3)	0.005 (3)	0.010 (2)
C4	0.046 (3)	0.039 (2)	0.048 (3)	0.001 (2)	0.000 (2)	0.004 (2)
C5	0.081 (4)	0.045 (3)	0.048 (3)	−0.001 (3)	0.005 (3)	0.006 (2)
C6	0.075 (4)	0.036 (2)	0.060 (3)	0.005 (3)	0.007 (3)	0.012 (2)
C7	0.049 (3)	0.044 (3)	0.049 (3)	0.003 (2)	0.001 (2)	0.005 (2)
C8	0.067 (4)	0.040 (2)	0.053 (3)	0.000 (2)	−0.001 (3)	0.006 (2)
C9	0.058 (3)	0.040 (2)	0.047 (3)	0.005 (2)	0.000 (2)	0.003 (2)
C10	0.049 (3)	0.035 (2)	0.048 (3)	0.004 (2)	−0.003 (2)	0.002 (2)
C11	0.059 (3)	0.039 (2)	0.038 (2)	0.003 (2)	−0.007 (2)	−0.001 (2)
C12	0.052 (3)	0.032 (2)	0.042 (3)	−0.001 (2)	0.000 (2)	−0.003 (2)
C13	0.064 (3)	0.036 (2)	0.037 (2)	−0.004 (2)	−0.005 (2)	0.006 (2)
C14	0.101 (4)	0.040 (2)	0.041 (3)	0.003 (3)	0.002 (3)	0.002 (2)
C15	0.088 (4)	0.030 (2)	0.052 (3)	0.004 (2)	0.003 (3)	−0.003 (2)
C16	0.075 (4)	0.048 (3)	0.044 (3)	−0.001 (3)	−0.001 (3)	−0.002 (2)
C17	0.086 (4)	0.050 (3)	0.049 (3)	−0.004 (3)	−0.004 (3)	−0.008 (2)
C18	0.092 (4)	0.041 (2)	0.046 (3)	−0.002 (3)	−0.012 (3)	0.005 (2)
C19	0.069 (4)	0.042 (3)	0.041 (3)	−0.002 (3)	−0.006 (3)	−0.005 (2)
N1	0.051 (4)	0.049 (3)	0.042 (2)	−0.004 (3)	−0.003 (3)	0.000 (2)
N2	0.046 (4)	0.038 (2)	0.049 (3)	0.001 (2)	−0.007 (3)	0.000 (2)
C20	0.060 (4)	0.040 (2)	0.031 (2)	0.005 (3)	0.001 (3)	0.000 (2)
C21	0.064 (5)	0.055 (3)	0.055 (3)	−0.002 (4)	0.009 (4)	0.000 (3)
C22	0.061 (6)	0.040 (3)	0.045 (3)	0.008 (4)	0.005 (4)	0.001 (3)
C23	0.064 (5)	0.048 (4)	0.035 (3)	0.003 (4)	0.002 (4)	−0.001 (3)
C24	0.059 (4)	0.070 (4)	0.036 (3)	0.003 (4)	−0.005 (3)	−0.014 (3)
C25	0.053 (4)	0.053 (3)	0.026 (2)	0.013 (3)	−0.007 (3)	−0.008 (2)
O1WA	0.090 (4)	0.111 (5)	0.094 (4)	−0.011 (4)	0.004 (3)	−0.003 (4)
N1B	0.051 (4)	0.049 (3)	0.042 (2)	−0.004 (3)	−0.003 (3)	0.000 (2)
N2B	0.046 (4)	0.038 (2)	0.049 (3)	0.001 (2)	−0.007 (3)	0.000 (2)
C20B	0.060 (4)	0.040 (2)	0.031 (2)	0.005 (3)	0.001 (3)	0.000 (2)
C21B	0.064 (5)	0.055 (3)	0.055 (3)	−0.002 (4)	0.009 (4)	0.000 (3)
C22B	0.061 (6)	0.040 (3)	0.045 (3)	0.008 (4)	0.005 (4)	0.001 (3)
C23B	0.064 (5)	0.048 (4)	0.035 (3)	0.003 (4)	0.002 (4)	−0.001 (3)
C24B	0.059 (4)	0.070 (4)	0.036 (3)	0.003 (4)	−0.005 (3)	−0.014 (3)
C25B	0.053 (4)	0.053 (3)	0.026 (2)	0.013 (3)	−0.007 (3)	−0.008 (2)
O1WB	0.090 (4)	0.111 (5)	0.094 (4)	−0.011 (4)	0.004 (3)	−0.003 (4)

Geometric parameters (Å, º) top

Br1—C1	1.888 (4)	C18—H18B	0.9700
O1—C7	1.225 (5)	C19—N2	1.212 (13)
O2—C12	1.356 (5)	C19—N1B	1.249 (14)
O2—C16	1.433 (5)	C19—N1	1.422 (14)
O3—C13	1.375 (5)	C19—N2B	1.431 (14)
O3—C18	1.424 (5)	N1—C25	1.365 (13)
C1—C2	1.372 (6)	N2—C20	1.404 (14)
C1—C6	1.372 (6)	N2—H2B	0.8600
C2—C3	1.383 (6)	C20—C21	1.3900
C2—H2A	0.9300	C20—C25	1.3900
C3—C4	1.382 (6)	C21—C22	1.3900
C3—H3A	0.9300	C21—H21A	0.9300
C4—C5	1.375 (6)	C22—C23	1.3900
C4—C7	1.504 (6)	C22—H22A	0.9300
C5—C6	1.373 (6)	C23—C24	1.3900
C5—H5A	0.9300	C23—H23A	0.9300
C6—H6A	0.9300	C24—C25	1.3900
C7—C8	1.452 (6)	C24—H24A	0.9300
C8—C9	1.318 (6)	O1WA—H1W1	0.82 (2)
C8—H8A	0.9300	O1WA—H1W2	0.82 (2)
C9—C10	1.463 (6)	O1WA—H1W3	0.25 (9)
C9—H9A	0.9300	O1WA—H1W4	1.47 (4)
C10—C15	1.385 (7)	N1B—C25B	1.359 (14)
C10—C11	1.391 (6)	N2B—C20B	1.343 (15)
C11—C12	1.370 (6)	N2B—H2BA	0.8600
C11—H11A	0.9300	C20B—C21B	1.3900
C12—C13	1.407 (6)	C20B—C25B	1.3900
C13—C14	1.371 (6)	C21B—C22B	1.3900
C14—C15	1.390 (6)	C21B—H21B	0.9300
C14—H14A	0.9300	C22B—C23B	1.3900
C15—H15A	0.9300	C22B—H22B	0.9300
C16—C17	1.493 (6)	C23B—C24B	1.3900
C16—H16A	0.9700	C23B—H23B	0.9300
C16—H16B	0.9700	C24B—C25B	1.3900
C17—H17A	0.9600	C24B—H24B	0.9300
C17—H17B	0.9600	O1WB—H1W1	1.05 (7)
C17—H17C	0.9600	O1WB—H1W2	0.90 (8)
C18—C19	1.490 (6)	O1WB—H1W3	0.82 (2)
C18—H18A	0.9700	O1WB—H1W4	0.82 (2)

C12—O2—C16	117.4 (3)	N2—C19—N1	116.4 (8)
C13—O3—C18	115.4 (3)	N1B—C19—N1	13.2 (10)
C2—C1—C6	120.3 (4)	N2—C19—N2B	10.3 (11)
C2—C1—Br1	120.7 (4)	N1B—C19—N2B	110.8 (9)
C6—C1—Br1	119.0 (3)	N1—C19—N2B	123.7 (8)
C1—C2—C3	119.4 (5)	N2—C19—C18	126.3 (8)
C1—C2—H2A	120.3	N1B—C19—C18	129.9 (7)
C3—C2—H2A	120.3	N1—C19—C18	117.0 (6)
C4—C3—C2	120.9 (4)	N2B—C19—C18	119.3 (7)
C4—C3—H3A	119.5	C25—N1—C19	99.7 (8)
C2—C3—H3A	119.5	C19—N2—C20	107.9 (10)
C5—C4—C3	118.4 (4)	C19—N2—H2B	126.1
C5—C4—C7	117.8 (4)	C20—N2—H2B	126.1
C3—C4—C7	123.8 (4)	C21—C20—C25	120.0
C6—C5—C4	121.0 (4)	C21—C20—N2	135.5 (7)
C6—C5—H5A	119.5	C25—C20—N2	104.3 (6)
C4—C5—H5A	119.5	C22—C21—C20	120.0
C1—C6—C5	119.9 (4)	C22—C21—H21A	120.0
C1—C6—H6A	120.0	C20—C21—H21A	120.0
C5—C6—H6A	120.0	C23—C22—C21	120.0
O1—C7—C8	120.7 (4)	C23—C22—H22A	120.0
O1—C7—C4	119.0 (4)	C21—C22—H22A	120.0
C8—C7—C4	120.3 (4)	C22—C23—C24	120.0
C9—C8—C7	122.3 (5)	C22—C23—H23A	120.0
C9—C8—H8A	118.8	C24—C23—H23A	120.0
C7—C8—H8A	118.8	C25—C24—C23	120.0
C8—C9—C10	128.8 (4)	C25—C24—H24A	120.0
C8—C9—H9A	115.6	C23—C24—H24A	120.0
C10—C9—H9A	115.6	N1—C25—C24	128.5 (7)
C15—C10—C11	118.3 (4)	N1—C25—C20	111.5 (7)
C15—C10—C9	121.6 (4)	C24—C25—C20	120.0
C11—C10—C9	120.0 (4)	H1W1—O1WA—H1W2	105 (3)
C12—C11—C10	122.6 (4)	H1W1—O1WA—H1W3	131 (10)
C12—C11—H11A	118.7	H1W2—O1WA—H1W3	92 (10)
C10—C11—H11A	118.7	H1W1—O1WA—H1W4	94 (7)
O2—C12—C11	126.0 (4)	H1W2—O1WA—H1W4	81 (9)
O2—C12—C13	115.4 (4)	H1W3—O1WA—H1W4	43 (8)
C11—C12—C13	118.6 (4)	C19—N1B—C25B	110.6 (10)
C14—C13—O3	124.9 (4)	C20B—N2B—C19	103.3 (10)
C14—C13—C12	119.3 (4)	C20B—N2B—H2BA	128.4
O3—C13—C12	115.8 (4)	C19—N2B—H2BA	128.4
C13—C14—C15	121.5 (4)	N2B—C20B—C21B	130.2 (7)
C13—C14—H14A	119.2	N2B—C20B—C25B	109.7 (7)
C15—C14—H14A	119.2	C21B—C20B—C25B	120.0
C10—C15—C14	119.6 (4)	C22B—C21B—C20B	120.0
C10—C15—H15A	120.2	C22B—C21B—H21B	120.0
C14—C15—H15A	120.2	C20B—C21B—H21B	120.0
O2—C16—C17	107.8 (4)	C21B—C22B—C23B	120.0
O2—C16—H16A	110.2	C21B—C22B—H22B	120.0
C17—C16—H16A	110.2	C23B—C22B—H22B	120.0
O2—C16—H16B	110.2	C24B—C23B—C22B	120.0
C17—C16—H16B	110.2	C24B—C23B—H23B	120.0
H16A—C16—H16B	108.5	C22B—C23B—H23B	120.0
C16—C17—H17A	109.5	C23B—C24B—C25B	120.0
C16—C17—H17B	109.5	C23B—C24B—H24B	120.0
H17A—C17—H17B	109.5	C25B—C24B—H24B	120.0
C16—C17—H17C	109.5	N1B—C25B—C24B	134.5 (8)
H17A—C17—H17C	109.5	N1B—C25B—C20B	105.5 (8)
H17B—C17—H17C	109.5	C24B—C25B—C20B	120.0
O3—C18—C19	109.2 (4)	H1W1—O1WB—H1W2	83 (6)
O3—C18—H18A	109.8	H1W1—O1WB—H1W3	64 (7)
C19—C18—H18A	109.8	H1W2—O1WB—H1W3	60 (7)
O3—C18—H18B	109.8	H1W1—O1WB—H1W4	136 (9)
C19—C18—H18B	109.8	H1W2—O1WB—H1W4	131 (10)
H18A—C18—H18B	108.3	H1W3—O1WB—H1W4	106 (3)
N2—C19—N1B	103.2 (9)

C6—C1—C2—C3	2.1 (7)	N2B—C19—N1—C25	6.0 (13)
Br1—C1—C2—C3	−178.3 (4)	C18—C19—N1—C25	−176.4 (6)
C1—C2—C3—C4	0.6 (8)	N1B—C19—N2—C20	6.0 (12)
C2—C3—C4—C5	−2.2 (7)	N1—C19—N2—C20	4.7 (13)
C2—C3—C4—C7	177.0 (4)	N2B—C19—N2—C20	−132 (7)
C3—C4—C5—C6	1.1 (7)	C18—C19—N2—C20	178.0 (6)
C7—C4—C5—C6	−178.1 (4)	C19—N2—C20—C21	−179.9 (6)
C2—C1—C6—C5	−3.2 (8)	C19—N2—C20—C25	−4.9 (10)
Br1—C1—C6—C5	177.2 (4)	C25—C20—C21—C22	0.0
C4—C5—C6—C1	1.6 (8)	N2—C20—C21—C22	174.4 (10)
C5—C4—C7—O1	6.2 (7)	C20—C21—C22—C23	0.0
C3—C4—C7—O1	−172.9 (5)	C21—C22—C23—C24	0.0
C5—C4—C7—C8	−175.7 (4)	C22—C23—C24—C25	0.0
C3—C4—C7—C8	5.1 (7)	C19—N1—C25—C24	178.4 (5)
O1—C7—C8—C9	3.9 (7)	C19—N1—C25—C20	−1.0 (9)
C4—C7—C8—C9	−174.1 (4)	C23—C24—C25—N1	−179.4 (10)
C7—C8—C9—C10	−179.5 (4)	C23—C24—C25—C20	0.0
C8—C9—C10—C15	−12.1 (8)	C21—C20—C25—N1	179.5 (8)
C8—C9—C10—C11	165.7 (5)	N2—C20—C25—N1	3.5 (9)
C15—C10—C11—C12	2.4 (7)	C21—C20—C25—C24	0.0
C9—C10—C11—C12	−175.4 (4)	N2—C20—C25—C24	−176.0 (7)
C16—O2—C12—C11	2.4 (6)	N2—C19—N1B—C25B	−5.4 (13)
C16—O2—C12—C13	−178.1 (4)	N1—C19—N1B—C25B	170 (6)
C10—C11—C12—O2	177.9 (4)	N2B—C19—N1B—C25B	2.0 (13)
C10—C11—C12—C13	−1.5 (7)	C18—C19—N1B—C25B	−177.0 (6)
C18—O3—C13—C14	8.9 (7)	N2—C19—N2B—C20B	41 (6)
C18—O3—C13—C12	−169.6 (4)	N1B—C19—N2B—C20B	−3.3 (12)
O2—C12—C13—C14	179.4 (4)	N1—C19—N2B—C20B	−6.6 (13)
C11—C12—C13—C14	−1.1 (7)	C18—C19—N2B—C20B	175.8 (6)
O2—C12—C13—O3	−1.9 (6)	C19—N2B—C20B—C21B	−178.7 (5)
C11—C12—C13—O3	177.6 (4)	C19—N2B—C20B—C25B	3.2 (10)
O3—C13—C14—C15	−175.8 (5)	N2B—C20B—C21B—C22B	−177.9 (10)
C12—C13—C14—C15	2.7 (8)	C25B—C20B—C21B—C22B	0.0
C11—C10—C15—C14	−0.8 (7)	C20B—C21B—C22B—C23B	0.0
C9—C10—C15—C14	177.0 (5)	C21B—C22B—C23B—C24B	0.0
C13—C14—C15—C10	−1.8 (8)	C22B—C23B—C24B—C25B	0.0
C12—O2—C16—C17	−178.2 (4)	C19—N1B—C25B—C24B	179.4 (6)
C13—O3—C18—C19	172.1 (4)	C19—N1B—C25B—C20B	0.1 (12)
O3—C18—C19—N2	86.4 (9)	C23B—C24B—C25B—N1B	−179.2 (11)
O3—C18—C19—N1B	−103.7 (10)	C23B—C24B—C25B—C20B	0.0
O3—C18—C19—N1	−100.3 (7)	N2B—C20B—C25B—N1B	−2.3 (10)
O3—C18—C19—N2B	77.4 (8)	C21B—C20B—C25B—N1B	179.4 (8)
N2—C19—N1—C25	−2.4 (12)	N2B—C20B—C25B—C24B	178.3 (8)
N1B—C19—N1—C25	−8 (4)	C21B—C20B—C25B—C24B	0.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N2Bⁱ	0.86	2.10	2.908 (9)	157
N2B—H2BA···N2ⁱ	0.86	2.06	2.908 (9)	172
O1WA—H1W1···O1WAⁱⁱ	0.82 (2)	1.89 (3)	2.69 (2)	164 (7)
O1WA—H1W2···N1	0.82 (2)	1.87 (2)	2.674 (16)	166 (6)
O1WA—H1W2···N1B	0.82 (2)	2.20 (3)	2.997 (17)	164 (6)
O1WB—H1W4···O1ⁱⁱⁱ	0.82 (2)	2.33 (7)	2.912 (11)	129 (8)

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

Experimental details

Crystal data
Chemical formula	C₂₅H₂₁BrN₂O₃·H₂O
M_r	495.36
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	295
a, b, c (Å)	13.8406 (12), 16.5192 (8), 19.4719 (13)
V (Å³)	4452.0 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.88
Crystal size (mm)	0.52 × 0.38 × 0.31

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.518, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	18755, 4033, 2083
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.160, 1.04
No. of reflections	4033
No. of parameters	305
No. of restraints	114
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.36

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N2Bⁱ	0.86	2.10	2.908 (9)	157
N2B—H2BA···N2ⁱ	0.86	2.06	2.908 (9)	172
O1WA—H1W1···O1WAⁱⁱ	0.82 (2)	1.89 (3)	2.69 (2)	164 (7)
O1WA—H1W2···N1	0.82 (2)	1.87 (2)	2.674 (16)	166 (6)
O1WA—H1W2···N1B	0.82 (2)	2.20 (3)	2.997 (17)	164 (6)
O1WB—H1W4···O1ⁱⁱⁱ	0.82 (2)	2.33 (7)	2.912 (11)	129 (8)

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

Acknowledgements

SS thanks Mangalore University and the UGC SAP for financial assistance for the purchase of chemicals. JPJ thanks Dr Ray J. Butcher and the Howard University Department of Chemistry for their assistance with the data collection. The diffractometer was funded by NSF grant No. CHE-0619278.

References

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Volume 67| Part 4| April 2011| Pages o834-o835

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

(2E)-3-{4-[(1H-1,3-Benzimidazol-2-yl)meth­­oxy]-3-eth­­oxy­phen­yl}-1-(4-bromo­phen­yl)prop-2-en-1-one monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(2E)-3-{4-[(1H-1,3-Benzimidazol-2-yl)methoxy]-3-ethoxyphenyl}-1-(4-bromophenyl)prop-2-en-1-one monohydrate