Ethyl 2-(4-hy­droxy-3-meth­oxy­phen­yl)-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate monohydrate

Yoon, Y.K.; Ali, M.A.; Choon, T.S.; Asik, S.I.J.; Razak, I.A.

doi:10.1107/S1600536811052391

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Pages o87-o88

doi:10.1107/S1600536811052391

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Ethyl 2-(4-hydroxy-3-methoxyphenyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-benzimidazole-5-carboxylate monohydrate

Yeong Keng Yoon,^a Mohamed Ashraf Ali,^a Tan Soo Choon,^a Safra Izuani Jama Asik ^b and Ibrahim Abdul Razak ^b ^*‡

^aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia, and ^bSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: arazaki@usm.my

(Received 30 November 2011; accepted 5 December 2011; online 10 December 2011)

In the title compound, C₂₄H₂₇N₃O₅·H₂O, the essentially planar benzimidazole ring system [maximum deviation = 0.020 (1) Å] forms dihedral angles of 54.10 (11) and 67.79 (6)°, respectively, with the mean plane of pyrrolidin-2-one ring and the benzene ring. The pyrrolidin-2-one ring adopts an envelope conformation with one of the methylene C atoms at the flap. An intramolecular C—H⋯π interaction is observed. In the crystal, O—H⋯O and O—H⋯N hydrogen bonds link the two components into a double-tape structure along the a axis. The crystal packing is further stabilized by weak π–π stacking [centroid–centroid distance = 3.6632 (9) Å] and C—H⋯O interactions.

Related literature

For the biological activity of benzimidazole derivatives, see: Rao et al. (2002 ); Thakurdesai et al. (2007 ); Dubey & Sanyal (2010 ). For related structures, see: Yoon et al. (2011 ). For the ring conformation, see: Cremer & Pople (1975).

Experimental

Crystal data

C₂₄H₂₇N₃O₅·H₂O
M_r = 455.50
Triclinic, $[P \overline 1]$
a = 9.7460 (8) Å
b = 10.0436 (8) Å
c = 12.6072 (10) Å
α = 85.737 (1)°
β = 89.684 (2)°
γ = 70.238 (1)°
V = 1157.91 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.43 × 0.32 × 0.16 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.960, T_max = 0.985
18195 measured reflections
6686 independent reflections
4485 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.185
S = 1.07
6686 reflections
312 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C8–C13 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2W1⋯O2ⁱ	0.85 (3)	2.06 (3)	2.879 (2)	164 (2)
O1W—H1W1⋯N1ⁱⁱ	0.95 (3)	1.90 (3)	2.8416 (19)	176 (2)
O4—H1O4⋯O1W	0.88 (3)	1.80 (3)	2.675 (2)	169 (3)
C16—H16A⋯O5ⁱⁱⁱ	0.96	2.44	3.380 (3)	166
C20—H20B⋯Cg4	0.97	2.86	3.750 (3)	153
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z+1; (iii) x-1, y, z-1.

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/S1600536811052391/is5022sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811052391/is5022Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811052391/is5022Isup3.cml

checkCIF report

Comment top

Benzimidazole derivatives are of wide interest because of their diverse biological activities and various clinical applications. This ring system is present in numerous anti-HIV (Rao et al., 2002), anti-inflammatory (Thakurdesai et al., 2007) and anthelmintics (Dubey and Sanyal, 2010) drugs. As part of our ongoing 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 benzimidazole (N1/N2/C1–C7) ring system is essentially planar with a maximum deviation of 0.020 (1) Å for atom N2. Dihedral angles of benzimidazole, (N1/N2/C1–C7) ring with the mean plane of pyrrolidin-2-one ring (N3/C20–C23) and the 2-methoxyphenol (C8–C13) ring are 54.10 (11) and 67.79 (6)°, respectively. The pyrrolidin-2-one ring adopts an envelope conformation with puckering parameters of Q = 0.148 (3) Å and ϕ = 78.5 (10)° (Cremer & Pople, 1975) with atom C21 at the flap, deviating by 0.095 (3) Å. In the crystal packing (Fig. 2), intermolecular O1W—H2W1···O2, O4—H1O4···O1W and O1W—H1W1···N1 hydrogen bonds link the molecules into a double-tape structure running along the a axis. There is a π–π stacking interaction between the benzene (C1–C6; centroid Cg3) rings with a Cg3···Cg3^iv distance of 3.6632 (9) Å [symmetry code: (iv) -x, -y, -z + 1]. The crystal packing is further stabilized by a C16—H16A···O5 hydrogen bond and a weak C20—H20B···Cg4 interaction (Table 1), where Cg4 is the centroid of the benzene (C8–C13) ring.

Related literature top

For the biological activity of benzimidazole derivatives, see: Rao et al. (2002); Thakurdesai et al. (2007); Dubey & Sanyal (2010). For related structures, see: Yoon et al. (2011). For the ring conformation, see: Cremer & Pople (1975).

Experimental top

Ethyl 3-amino-4-(3(2-oxopyrrolidin-1yl)propylamino)benzoate (0.84 mmol) and sodium metabisulfite adduct of 4-hydroxy-3-metoxybenzaldehyde (1.68 mmol) were dissolved in DMF. The reaction mixture was reflux at 130 °C for 2 hrs. 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 the evaporated in vacuo to yield the product. The product was recrystallized from ethyl acetate.

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 structure of the title compound, showing 50% probability displacement ellipsoids. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. The crystal packing, viewed along the a-axis. Hydrogen bonds are shown as dashed lines.

Ethyl 2-(4-hydroxy-3-methoxyphenyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]- 1H-benzimidazole-5-carboxylate monohydrate top

Crystal data top

C₂₄H₂₇N₃O₅·H₂O	Z = 2
M_r = 455.50	F(000) = 484
Triclinic, P1	D_x = 1.306 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7460 (8) Å	Cell parameters from 4470 reflections
b = 10.0436 (8) Å	θ = 2.5–29.5°
c = 12.6072 (10) Å	µ = 0.10 mm⁻¹
α = 85.737 (1)°	T = 296 K
β = 89.684 (2)°	Block, brown
γ = 70.238 (1)°	0.43 × 0.32 × 0.16 mm
V = 1157.91 (16) Å³

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	6686 independent reflections
Radiation source: fine-focus sealed tube	4485 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 30.1°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
T_min = 0.960, T_max = 0.985	k = −14→14
18195 measured reflections	l = −17→17

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.185	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0974P)² + 0.1068P] where P = (F_o² + 2F_c²)/3
6686 reflections	(Δ/σ)_max < 0.001
312 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₄H₂₇N₃O₅·H₂O	γ = 70.238 (1)°
M_r = 455.50	V = 1157.91 (16) Å³
Triclinic, P1	Z = 2
a = 9.7460 (8) Å	Mo Kα radiation
b = 10.0436 (8) Å	µ = 0.10 mm⁻¹
c = 12.6072 (10) Å	T = 296 K
α = 85.737 (1)°	0.43 × 0.32 × 0.16 mm
β = 89.684 (2)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	6686 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4485 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.985	R_int = 0.029
18195 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.185	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.30 e Å⁻³
6686 reflections	Δρ_min = −0.26 e Å⁻³
312 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	−0.17090 (17)	0.13373 (19)	0.18216 (12)	0.0762 (4)
O2	−0.35072 (14)	0.11827 (17)	0.28604 (13)	0.0702 (4)
O3	0.1298 (3)	0.2186 (2)	1.00505 (19)	0.1183 (8)
O4	0.64165 (13)	0.40228 (14)	0.73582 (10)	0.0538 (3)
O5	0.64019 (13)	0.14280 (12)	0.76404 (10)	0.0552 (3)
N1	0.17611 (13)	0.25473 (14)	0.43596 (10)	0.0416 (3)
N2	0.09463 (13)	0.23337 (13)	0.60105 (10)	0.0401 (3)
N3	0.12756 (16)	0.41105 (17)	0.89776 (11)	0.0529 (4)
C1	0.04959 (15)	0.21973 (15)	0.43129 (12)	0.0379 (3)
C2	−0.02368 (16)	0.19669 (16)	0.34357 (13)	0.0412 (3)
H2A	0.0100	0.2035	0.2749	0.049*
C3	−0.14954 (15)	0.16306 (15)	0.36302 (13)	0.0421 (3)
C4	−0.20115 (16)	0.15385 (17)	0.46613 (14)	0.0456 (4)
H4A	−0.2863	0.1325	0.4759	0.055*
C5	−0.12959 (16)	0.17542 (17)	0.55325 (13)	0.0443 (3)
H5A	−0.1636	0.1686	0.6218	0.053*
C6	−0.00288 (15)	0.20810 (15)	0.53349 (12)	0.0378 (3)
C7	0.19826 (15)	0.26220 (15)	0.53799 (12)	0.0386 (3)
C8	0.31855 (15)	0.29914 (16)	0.58469 (12)	0.0391 (3)
C9	0.42362 (16)	0.19835 (15)	0.65042 (12)	0.0419 (3)
H9A	0.4206	0.1068	0.6616	0.050*
C10	0.53227 (15)	0.23334 (15)	0.69912 (12)	0.0397 (3)
C11	0.53539 (16)	0.37285 (16)	0.68324 (12)	0.0399 (3)
C12	0.43197 (17)	0.47134 (16)	0.61670 (13)	0.0436 (3)
H12A	0.4346	0.5630	0.6051	0.052*
C13	0.32404 (17)	0.43507 (16)	0.56685 (13)	0.0437 (3)
H13A	0.2557	0.5019	0.5216	0.052*
C14	−0.23434 (18)	0.13642 (17)	0.27471 (15)	0.0492 (4)
C15	−0.2499 (4)	0.1148 (4)	0.0897 (2)	0.1125 (11)
H15A	−0.2417	0.0159	0.0893	0.135*
H15B	−0.3524	0.1707	0.0942	0.135*
C16	−0.1953 (5)	0.1561 (5)	−0.0036 (3)	0.1330 (14)
H16A	−0.2453	0.1380	−0.0633	0.199*
H16B	−0.0930	0.1034	−0.0068	0.199*
H16C	−0.2095	0.2556	−0.0055	0.199*
C17	0.07375 (17)	0.25520 (17)	0.71444 (12)	0.0440 (3)
H17A	0.1679	0.2234	0.7510	0.053*
H17B	0.0174	0.1990	0.7447	0.053*
C18	−0.00473 (18)	0.41025 (18)	0.73095 (13)	0.0489 (4)
H18A	−0.1024	0.4388	0.7003	0.059*
H18B	0.0462	0.4669	0.6936	0.059*
C19	−0.01470 (19)	0.4404 (2)	0.84774 (15)	0.0574 (4)
H19A	−0.0725	0.5393	0.8537	0.069*
H19B	−0.0644	0.3828	0.8853	0.069*
C20	0.2172 (3)	0.4956 (3)	0.86944 (19)	0.0786 (7)
H20A	0.1655	0.5951	0.8783	0.094*
H20B	0.2485	0.4851	0.7964	0.094*
C21	0.3479 (3)	0.4349 (4)	0.9482 (2)	0.0957 (9)
H21A	0.4390	0.4191	0.9113	0.115*
H21B	0.3420	0.4996	1.0028	0.115*
C22	0.3385 (3)	0.2990 (3)	0.9957 (2)	0.0910 (8)
H22A	0.3541	0.2909	1.0721	0.109*
H22B	0.4112	0.2194	0.9659	0.109*
C23	0.1884 (3)	0.3012 (2)	0.96930 (17)	0.0675 (5)
C24	0.6452 (2)	−0.0001 (2)	0.7783 (2)	0.0696 (6)
H24A	0.7301	−0.0550	0.8204	0.104*
H24B	0.6497	−0.0381	0.7102	0.104*
H24C	0.5593	−0.0041	0.8141	0.104*
O1W	0.63716 (17)	0.67068 (15)	0.71300 (12)	0.0565 (3)
H2W1	0.556 (3)	0.736 (3)	0.7004 (18)	0.073 (7)*
H1W1	0.703 (3)	0.695 (2)	0.6663 (19)	0.076 (7)*
H1O4	0.630 (3)	0.493 (3)	0.7238 (18)	0.075 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0729 (9)	0.1176 (13)	0.0612 (9)	−0.0609 (9)	−0.0102 (7)	−0.0141 (8)
O2	0.0485 (7)	0.0835 (10)	0.0904 (10)	−0.0369 (7)	−0.0121 (7)	−0.0103 (8)
O3	0.1466 (19)	0.0967 (14)	0.1279 (17)	−0.0717 (14)	−0.0518 (14)	0.0407 (12)
O4	0.0477 (6)	0.0476 (7)	0.0739 (8)	−0.0271 (5)	−0.0160 (6)	−0.0001 (6)
O5	0.0519 (6)	0.0420 (6)	0.0730 (8)	−0.0197 (5)	−0.0242 (6)	0.0066 (5)
N1	0.0363 (6)	0.0502 (7)	0.0435 (7)	−0.0221 (5)	−0.0036 (5)	−0.0006 (5)
N2	0.0382 (6)	0.0431 (7)	0.0430 (7)	−0.0192 (5)	−0.0022 (5)	−0.0026 (5)
N3	0.0548 (8)	0.0617 (9)	0.0458 (8)	−0.0234 (7)	−0.0013 (6)	−0.0086 (6)
C1	0.0316 (6)	0.0379 (7)	0.0462 (8)	−0.0151 (6)	−0.0041 (5)	0.0001 (6)
C2	0.0367 (7)	0.0432 (8)	0.0460 (8)	−0.0171 (6)	−0.0052 (6)	−0.0011 (6)
C3	0.0338 (7)	0.0362 (7)	0.0577 (9)	−0.0139 (6)	−0.0086 (6)	−0.0017 (6)
C4	0.0337 (7)	0.0423 (8)	0.0641 (10)	−0.0177 (6)	−0.0005 (7)	−0.0005 (7)
C5	0.0383 (7)	0.0458 (8)	0.0514 (9)	−0.0186 (6)	0.0033 (6)	−0.0004 (6)
C6	0.0337 (6)	0.0348 (7)	0.0457 (8)	−0.0131 (5)	−0.0038 (5)	0.0002 (5)
C7	0.0346 (7)	0.0388 (7)	0.0443 (8)	−0.0155 (6)	−0.0037 (6)	−0.0003 (6)
C8	0.0364 (7)	0.0419 (7)	0.0423 (8)	−0.0180 (6)	−0.0025 (6)	−0.0020 (6)
C9	0.0419 (7)	0.0351 (7)	0.0528 (9)	−0.0189 (6)	−0.0077 (6)	−0.0008 (6)
C10	0.0365 (7)	0.0366 (7)	0.0473 (8)	−0.0145 (6)	−0.0073 (6)	0.0006 (6)
C11	0.0360 (7)	0.0406 (7)	0.0478 (8)	−0.0191 (6)	0.0000 (6)	−0.0047 (6)
C12	0.0432 (8)	0.0378 (7)	0.0545 (9)	−0.0208 (6)	−0.0018 (6)	0.0015 (6)
C13	0.0417 (7)	0.0418 (8)	0.0491 (8)	−0.0176 (6)	−0.0066 (6)	0.0039 (6)
C14	0.0426 (8)	0.0444 (8)	0.0645 (11)	−0.0203 (7)	−0.0120 (7)	−0.0002 (7)
C15	0.124 (2)	0.192 (3)	0.0685 (16)	−0.112 (3)	−0.0155 (15)	−0.0232 (18)
C16	0.184 (4)	0.162 (3)	0.088 (2)	−0.108 (3)	−0.050 (2)	0.003 (2)
C17	0.0454 (8)	0.0480 (8)	0.0404 (8)	−0.0189 (7)	−0.0021 (6)	−0.0004 (6)
C18	0.0408 (8)	0.0543 (9)	0.0485 (9)	−0.0118 (7)	−0.0045 (6)	−0.0056 (7)
C19	0.0480 (9)	0.0665 (11)	0.0564 (10)	−0.0157 (8)	0.0059 (8)	−0.0154 (8)
C20	0.0812 (14)	0.1101 (19)	0.0640 (12)	−0.0598 (14)	−0.0060 (11)	0.0033 (12)
C21	0.0717 (15)	0.157 (3)	0.0758 (15)	−0.0603 (18)	−0.0095 (12)	−0.0113 (16)
C22	0.0764 (15)	0.103 (2)	0.0856 (17)	−0.0190 (15)	−0.0253 (13)	−0.0107 (14)
C23	0.0776 (13)	0.0626 (12)	0.0628 (12)	−0.0239 (11)	−0.0135 (10)	−0.0052 (9)
C24	0.0683 (12)	0.0404 (9)	0.0982 (16)	−0.0193 (9)	−0.0323 (11)	0.0140 (9)
O1W	0.0552 (7)	0.0477 (7)	0.0723 (9)	−0.0254 (6)	0.0088 (6)	−0.0028 (6)

Geometric parameters (Å, º) top

O1—C14	1.315 (2)	C11—C12	1.382 (2)
O1—C15	1.460 (2)	C12—C13	1.391 (2)
O2—C14	1.214 (2)	C12—H12A	0.9300
O3—C23	1.216 (3)	C13—H13A	0.9300
O4—C11	1.3575 (17)	C15—C16	1.382 (5)
O4—H1O4	0.88 (3)	C15—H15A	0.9700
O5—C10	1.3621 (18)	C15—H15B	0.9700
O5—C24	1.418 (2)	C16—H16A	0.9600
N1—C7	1.317 (2)	C16—H16B	0.9600
N1—C1	1.3944 (17)	C16—H16C	0.9600
N2—C7	1.3750 (19)	C17—C18	1.515 (2)
N2—C6	1.3774 (18)	C17—H17A	0.9700
N2—C17	1.465 (2)	C17—H17B	0.9700
N3—C23	1.341 (3)	C18—C19	1.521 (2)
N3—C20	1.437 (3)	C18—H18A	0.9700
N3—C19	1.453 (2)	C18—H18B	0.9700
C1—C2	1.395 (2)	C19—H19A	0.9700
C1—C6	1.395 (2)	C19—H19B	0.9700
C2—C3	1.394 (2)	C20—C21	1.542 (3)
C2—H2A	0.9300	C20—H20A	0.9700
C3—C4	1.399 (2)	C20—H20B	0.9700
C3—C14	1.483 (2)	C21—C22	1.481 (4)
C4—C5	1.373 (2)	C21—H21A	0.9700
C4—H4A	0.9300	C21—H21B	0.9700
C5—C6	1.398 (2)	C22—C23	1.494 (3)
C5—H5A	0.9300	C22—H22A	0.9700
C7—C8	1.4808 (19)	C22—H22B	0.9700
C8—C13	1.386 (2)	C24—H24A	0.9600
C8—C9	1.394 (2)	C24—H24B	0.9600
C9—C10	1.3830 (19)	C24—H24C	0.9600
C9—H9A	0.9300	O1W—H2W1	0.85 (3)
C10—C11	1.411 (2)	O1W—H1W1	0.95 (3)

C14—O1—C15	117.16 (17)	C16—C15—H15B	109.4
C11—O4—H1O4	109.2 (16)	O1—C15—H15B	109.4
C10—O5—C24	117.13 (13)	H15A—C15—H15B	108.0
C7—N1—C1	104.76 (12)	C15—C16—H16A	109.5
C7—N2—C6	106.56 (12)	C15—C16—H16B	109.5
C7—N2—C17	126.45 (12)	H16A—C16—H16B	109.5
C6—N2—C17	125.80 (13)	C15—C16—H16C	109.5
C23—N3—C20	114.78 (18)	H16A—C16—H16C	109.5
C23—N3—C19	123.57 (18)	H16B—C16—H16C	109.5
C20—N3—C19	121.59 (17)	N2—C17—C18	110.95 (13)
N1—C1—C2	129.84 (14)	N2—C17—H17A	109.4
N1—C1—C6	109.94 (12)	C18—C17—H17A	109.4
C2—C1—C6	120.21 (13)	N2—C17—H17B	109.4
C3—C2—C1	117.26 (15)	C18—C17—H17B	109.4
C3—C2—H2A	121.4	H17A—C17—H17B	108.0
C1—C2—H2A	121.4	C17—C18—C19	112.78 (15)
C2—C3—C4	121.49 (14)	C17—C18—H18A	109.0
C2—C3—C14	121.05 (15)	C19—C18—H18A	109.0
C4—C3—C14	117.46 (14)	C17—C18—H18B	109.0
C5—C4—C3	121.84 (14)	C19—C18—H18B	109.0
C5—C4—H4A	119.1	H18A—C18—H18B	107.8
C3—C4—H4A	119.1	N3—C19—C18	112.58 (14)
C4—C5—C6	116.48 (15)	N3—C19—H19A	109.1
C4—C5—H5A	121.8	C18—C19—H19A	109.1
C6—C5—H5A	121.8	N3—C19—H19B	109.1
N2—C6—C1	105.75 (12)	C18—C19—H19B	109.1
N2—C6—C5	131.54 (14)	H19A—C19—H19B	107.8
C1—C6—C5	122.71 (13)	N3—C20—C21	103.2 (2)
N1—C7—N2	112.96 (12)	N3—C20—H20A	111.1
N1—C7—C8	125.86 (13)	C21—C20—H20A	111.1
N2—C7—C8	121.17 (13)	N3—C20—H20B	111.1
C13—C8—C9	119.76 (13)	C21—C20—H20B	111.1
C13—C8—C7	120.35 (13)	H20A—C20—H20B	109.1
C9—C8—C7	119.84 (13)	C22—C21—C20	105.7 (2)
C10—C9—C8	120.56 (13)	C22—C21—H21A	110.6
C10—C9—H9A	119.7	C20—C21—H21A	110.6
C8—C9—H9A	119.7	C22—C21—H21B	110.6
O5—C10—C9	125.15 (13)	C20—C21—H21B	110.6
O5—C10—C11	115.23 (12)	H21A—C21—H21B	108.7
C9—C10—C11	119.62 (13)	C21—C22—C23	106.0 (2)
O4—C11—C12	123.67 (13)	C21—C22—H22A	110.5
O4—C11—C10	117.02 (13)	C23—C22—H22A	110.5
C12—C11—C10	119.31 (13)	C21—C22—H22B	110.5
C11—C12—C13	120.81 (13)	C23—C22—H22B	110.5
C11—C12—H12A	119.6	H22A—C22—H22B	108.7
C13—C12—H12A	119.6	O3—C23—N3	125.0 (2)
C8—C13—C12	119.90 (14)	O3—C23—C22	126.9 (2)
C8—C13—H13A	120.1	N3—C23—C22	108.1 (2)
C12—C13—H13A	120.1	O5—C24—H24A	109.5
O2—C14—O1	122.90 (16)	O5—C24—H24B	109.5
O2—C14—C3	123.72 (18)	H24A—C24—H24B	109.5
O1—C14—C3	113.38 (14)	O5—C24—H24C	109.5
C16—C15—O1	111.0 (2)	H24A—C24—H24C	109.5
C16—C15—H15A	109.4	H24B—C24—H24C	109.5
O1—C15—H15A	109.4	H2W1—O1W—H1W1	105 (2)

C7—N1—C1—C2	−179.26 (15)	C8—C9—C10—C11	0.9 (2)
C7—N1—C1—C6	0.55 (16)	O5—C10—C11—O4	−1.7 (2)
N1—C1—C2—C3	−179.84 (15)	C9—C10—C11—O4	177.88 (14)
C6—C1—C2—C3	0.4 (2)	O5—C10—C11—C12	178.61 (14)
C1—C2—C3—C4	0.5 (2)	C9—C10—C11—C12	−1.8 (2)
C1—C2—C3—C14	−179.84 (13)	O4—C11—C12—C13	−178.67 (15)
C2—C3—C4—C5	−0.9 (2)	C10—C11—C12—C13	1.0 (2)
C14—C3—C4—C5	179.39 (14)	C9—C8—C13—C12	−1.7 (2)
C3—C4—C5—C6	0.4 (2)	C7—C8—C13—C12	175.77 (14)
C7—N2—C6—C1	1.43 (15)	C11—C12—C13—C8	0.7 (2)
C17—N2—C6—C1	169.57 (13)	C15—O1—C14—O2	3.1 (3)
C7—N2—C6—C5	−179.21 (16)	C15—O1—C14—C3	−177.2 (2)
C17—N2—C6—C5	−11.1 (3)	C2—C3—C14—O2	−173.74 (17)
N1—C1—C6—N2	−1.25 (16)	C4—C3—C14—O2	5.9 (2)
C2—C1—C6—N2	178.58 (13)	C2—C3—C14—O1	6.5 (2)
N1—C1—C6—C5	179.31 (14)	C4—C3—C14—O1	−173.82 (15)
C2—C1—C6—C5	−0.9 (2)	C14—O1—C15—C16	161.8 (3)
C4—C5—C6—N2	−178.83 (15)	C7—N2—C17—C18	77.86 (19)
C4—C5—C6—C1	0.4 (2)	C6—N2—C17—C18	−87.97 (18)
C1—N1—C7—N2	0.40 (17)	N2—C17—C18—C19	−173.95 (13)
C1—N1—C7—C8	−178.76 (14)	C23—N3—C19—C18	−108.7 (2)
C6—N2—C7—N1	−1.19 (17)	C20—N3—C19—C18	68.2 (2)
C17—N2—C7—N1	−169.23 (14)	C17—C18—C19—N3	63.3 (2)
C6—N2—C7—C8	178.01 (13)	C23—N3—C20—C21	−7.6 (3)
C17—N2—C7—C8	10.0 (2)	C19—N3—C20—C21	175.20 (18)
N1—C7—C8—C13	67.7 (2)	N3—C20—C21—C22	13.8 (3)
N2—C7—C8—C13	−111.44 (17)	C20—C21—C22—C23	−15.0 (3)
N1—C7—C8—C9	−114.92 (18)	C20—N3—C23—O3	178.6 (3)
N2—C7—C8—C9	65.99 (19)	C19—N3—C23—O3	−4.3 (3)
C13—C8—C9—C10	0.8 (2)	C20—N3—C23—C22	−1.7 (3)
C7—C8—C9—C10	−176.60 (14)	C19—N3—C23—C22	175.38 (18)
C24—O5—C10—C9	3.3 (3)	C21—C22—C23—O3	−169.5 (3)
C24—O5—C10—C11	−177.18 (17)	C21—C22—C23—N3	10.8 (3)
C8—C9—C10—O5	−179.58 (15)

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C8–C13 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W1···O2ⁱ	0.85 (3)	2.06 (3)	2.879 (2)	164 (2)
O1W—H1W1···N1ⁱⁱ	0.95 (3)	1.90 (3)	2.8416 (19)	176 (2)
O4—H1O4···O1W	0.88 (3)	1.80 (3)	2.675 (2)	169 (3)
C16—H16A···O5ⁱⁱⁱ	0.96	2.44	3.380 (3)	166
C20—H20B···Cg4	0.97	2.86	3.750 (3)	153

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

Experimental details

Crystal data
Chemical formula	C₂₄H₂₇N₃O₅·H₂O
M_r	455.50
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.7460 (8), 10.0436 (8), 12.6072 (10)
α, β, γ (°)	85.737 (1), 89.684 (2), 70.238 (1)
V (Å³)	1157.91 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.43 × 0.32 × 0.16

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.960, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	18195, 6686, 4485
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.185, 1.07
No. of reflections	6686
No. of parameters	312
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.26

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

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C8–C13 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W1···O2ⁱ	0.85 (3)	2.06 (3)	2.879 (2)	164 (2)
O1W—H1W1···N1ⁱⁱ	0.95 (3)	1.90 (3)	2.8416 (19)	176 (2)
O4—H1O4···O1W	0.88 (3)	1.80 (3)	2.675 (2)	169 (3)
C16—H16A···O5ⁱⁱⁱ	0.96	2.44	3.380 (3)	165.7
C20—H20B···Cg4	0.97	2.86	3.750 (3)	153

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

Footnotes

‡Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant Nos. 1001/PFIZIK/811151 and 1001/PSK/8620012. The authors also wish to express their thanks to the Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Molecular Medicine, Universiti of Sains Malaysia.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Dubey, A. K. & Sanyal, P. K. (2010). Vet Scan, 5, 63. Google Scholar
Rao, A., Chimirri, A., Clercq, E. D., Monforte, A. M., Monforte, P., Pannecouque, C. & Zappala, M. (2002). 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). Pharmacol. Online, 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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Volume 68| Part 1| January 2012| Pages o87-o88

doi:10.1107/S1600536811052391

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Ethyl 2-(4-hy­dr­oxy-3-meth­­oxy­phen­yl)-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate monohydrate

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Experimental

Crystal data

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organic compounds

Ethyl 2-(4-hydroxy-3-methoxyphenyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-benzimidazole-5-carboxylate monohydrate